Home Redetermination of the crystal structure of 5,14-dihydro-6,17-dimethyl-8,15-diphenyldibenzo(b,i)(1,4,8,11)tetra-azacyclotetradecine, C32H28N4
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Redetermination of the crystal structure of 5,14-dihydro-6,17-dimethyl-8,15-diphenyldibenzo(b,i)(1,4,8,11)tetra-azacyclotetradecine, C32H28N4

  • Lucky Dey , Saswata Rabi ORCID logo , Debashis Palit ORCID logo , Ismail M. M. Rahman ORCID logo EMAIL logo , Edward R. T. Tiekink ORCID logo EMAIL logo and Tapashi Ghosh Roy ORCID logo EMAIL logo
Published/Copyright: May 1, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 4

Abstract

C32H28N4, monoclinic, P21/c (no. 14), a = 17.7218(4) Å, b = 20.7769(5) Å, c = 14.9434(3) Å, β =  113.598 ( 3 ) ° , V = 5042.1(2) Å3, Z = 8, R gt (F) = 0.0519, wR ref (F 2) = 0.1544, T = 294 K.

CCDC no.: 2256334

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Red block
Size 0.14 × 0.08 × 0.05 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.57 mm−1
Diffractometer, scan mode: XtaLAB Synergy, ω
θ max, completeness: 67.1°, >99 %
N(hkl)measured, N(hkl)unique, R int: 61,154, 8987, 0.050
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 7152
N(param)refined: 662
Programs: CrysAlisPRO [1], SHELX [2, 3], WinGX/ORTEP [4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
N1 0.63057 (11) 0.21429 (9) 0.97094 (12) 0.0515 (4)
H1N 0.5858 (10) 0.2334 (11) 0.9335 (15) 0.062*
N2 0.53963 (10) 0.31781 (9) 0.88668 (12) 0.0517 (4)
N3 0.45995 (11) 0.25619 (9) 0.71711 (12) 0.0526 (4)
H3N 0.4877 (14) 0.2318 (10) 0.7655 (13) 0.063*
N4 0.55001 (10) 0.15062 (8) 0.79833 (11) 0.0456 (4)
C1 0.69313 (13) 0.25547 (11) 1.01063 (14) 0.0521 (5)
C2 0.68113 (14) 0.32139 (11) 0.99288 (15) 0.0555 (5)
H2 0.725192 0.348257 1.027389 0.067*
C3 0.60834 (13) 0.35110 (10) 0.92742 (14) 0.0503 (5)
C4 0.46386 (12) 0.34405 (10) 0.82207 (14) 0.0459 (4)
C5 0.42139 (12) 0.31133 (10) 0.73432 (14) 0.0463 (4)
C6 0.34326 (13) 0.33192 (12) 0.67237 (16) 0.0587 (5)
H6 0.314576 0.309940 0.614396 0.070*
C7 0.30793 (14) 0.38477 (12) 0.69627 (18) 0.0614 (6)
H7 0.255718 0.398349 0.654253 0.074*
C8 0.34964 (14) 0.41736 (11) 0.78193 (18) 0.0592 (6)
H8 0.325959 0.453294 0.797427 0.071*
C9 0.42695 (14) 0.39674 (10) 0.84525 (17) 0.0543 (5)
H9 0.454413 0.418393 0.903854 0.065*
C10 0.45917 (12) 0.23380 (10) 0.63292 (14) 0.0447 (4)
C11 0.49909 (13) 0.17745 (10) 0.63006 (14) 0.0495 (5)
H11 0.494599 0.163851 0.568840 0.059*
C12 0.54629 (12) 0.13794 (10) 0.71038 (14) 0.0473 (4)
C13 0.59362 (11) 0.11363 (10) 0.88233 (14) 0.0465 (4)
C14 0.63390 (12) 0.14656 (11) 0.97152 (14) 0.0488 (5)
C15 0.67159 (15) 0.11160 (13) 1.05728 (16) 0.0639 (6)
H15 0.696281 0.133264 1.116396 0.077*
C16 0.67291 (17) 0.04492 (14) 1.05598 (19) 0.0736 (7)
H16 0.699779 0.022136 1.113648 0.088*
C17 0.63464 (17) 0.01270 (13) 0.9697 (2) 0.0719 (7)
H17 0.635836 −0.032042 0.968731 0.086*
C18 0.59406 (14) 0.04654 (11) 0.88376 (17) 0.0594 (5)
H18 0.566599 0.024057 0.825942 0.071*
C19 0.77959 (14) 0.23247 (13) 1.06839 (17) 0.0651 (6)
H19Aa 0.815677 0.268865 1.090823 0.098*
H19Ba 0.781090 0.207909 1.123496 0.098*
H19Ca 0.797174 0.205952 1.027726 0.098*
H19Da 0.780284 0.186286 1.070540 0.098*
H19Ea 0.814870 0.247242 1.037867 0.098*
H19Fa 0.798787 0.249199 1.133637 0.098*
C20 0.61502 (13) 0.41936 (11) 0.89907 (15) 0.0505 (5)
C21 0.60038 (14) 0.43395 (13) 0.80336 (16) 0.0603 (6)
H21 0.585579 0.401381 0.756791 0.072*
C22 0.60753 (16) 0.49659 (15) 0.7760 (2) 0.0728 (7)
H22 0.598641 0.505655 0.711624 0.087*
C23 0.62777 (15) 0.54555 (14) 0.8439 (2) 0.0727 (7)
H23 0.631307 0.587755 0.825198 0.087*
C24 0.64254 (17) 0.53162 (13) 0.9384 (2) 0.0733 (7)
H24 0.655760 0.564557 0.984328 0.088*
C25 0.63804 (16) 0.46908 (12) 0.96673 (17) 0.0646 (6)
H25 0.650630 0.460077 1.032114 0.078*
C26 0.42112 (13) 0.27138 (10) 0.54026 (14) 0.0484 (5)
C27 0.35835 (16) 0.24507 (13) 0.46017 (17) 0.0683 (6)
H27 0.337628 0.204657 0.464771 0.082*
C28 0.3262 (2) 0.27863 (18) 0.3731 (2) 0.0947 (10)
H28 0.283336 0.260832 0.319670 0.114*
C29 0.3567 (2) 0.33777 (18) 0.3647 (2) 0.0915 (10)
H29 0.334418 0.360313 0.306089 0.110*
C30 0.4202 (2) 0.36344 (14) 0.4432 (2) 0.0793 (8)
H30 0.442011 0.403191 0.437417 0.095*
C31 0.45229 (16) 0.33075 (12) 0.53086 (19) 0.0634 (6)
H31 0.495143 0.348807 0.583974 0.076*
C32 0.59283 (17) 0.08498 (13) 0.68721 (19) 0.0698 (7)
H32Aa 0.580331 0.085081 0.618488 0.105*
H32Ba 0.650852 0.091519 0.723044 0.105*
H32Ca 0.577172 0.044361 0.705241 0.105*
H32Da 0.625239 0.062227 0.746027 0.105*
H32Ea 0.554718 0.055788 0.641471 0.105*
H32Fa 0.628397 0.102946 0.659275 0.105*
N5 0.85358 (11) 0.22182 (8) 0.83225 (13) 0.0510 (4)
H5N 0.8979 (10) 0.2418 (11) 0.8388 (17) 0.061*
N6 0.94547 (10) 0.32469 (8) 0.83876 (11) 0.0448 (4)
N7 1.01554 (11) 0.26686 (9) 0.73130 (12) 0.0506 (4)
H7N 0.9880 (13) 0.2453 (10) 0.7569 (16) 0.061*
N8 0.93210 (10) 0.15837 (8) 0.73492 (12) 0.0472 (4)
C33 0.79168 (13) 0.26388 (11) 0.81390 (14) 0.0497 (5)
C34 0.80484 (12) 0.32959 (10) 0.81409 (14) 0.0459 (4)
H34 0.761638 0.356465 0.810072 0.055*
C35 0.87906 (11) 0.35946 (10) 0.81993 (12) 0.0418 (4)
C36 1.02174 (11) 0.34914 (9) 0.84551 (13) 0.0401 (4)
C37 1.05892 (11) 0.31840 (9) 0.78982 (13) 0.0420 (4)
C38 1.13667 (12) 0.33829 (11) 0.79888 (15) 0.0501 (5)
H38 1.161355 0.318764 0.761440 0.060*
C39 1.17731 (13) 0.38686 (11) 0.86318 (15) 0.0543 (5)
H39 1.229049 0.400005 0.868318 0.065*
C40 1.14216 (13) 0.41601 (10) 0.91969 (15) 0.0522 (5)
H40 1.170388 0.448221 0.963535 0.063*
C41 1.06453 (12) 0.39726 (10) 0.91112 (14) 0.0469 (4)
H41 1.040814 0.416939 0.949458 0.056*
C42 1.01915 (12) 0.24155 (10) 0.65022 (14) 0.0461 (4)
C43 0.98189 (14) 0.18351 (10) 0.61373 (15) 0.0513 (5)
H43 0.986371 0.168880 0.557238 0.062*
C44 0.93749 (13) 0.14359 (10) 0.65261 (15) 0.0484 (5)
C45 0.89150 (12) 0.12105 (10) 0.78052 (14) 0.0476 (5)
C46 0.85081 (13) 0.15404 (10) 0.83057 (15) 0.0503 (5)
C47 0.81487 (17) 0.11901 (13) 0.88226 (19) 0.0697 (7)
H47 0.787946 0.140584 0.915489 0.084*
C48 0.81851 (19) 0.05206 (14) 0.8851 (2) 0.0783 (8)
H48 0.793666 0.029282 0.919594 0.094*
C49 0.85843 (17) 0.01985 (12) 0.8375 (2) 0.0701 (7)
H49 0.860548 −0.024882 0.839079 0.084*
C50 0.89547 (14) 0.05356 (11) 0.78708 (17) 0.0599 (6)
H50 0.923946 0.031159 0.756481 0.072*
C51 0.70504 (15) 0.24006 (13) 0.7823 (2) 0.0664 (6)
H51A 0.667922 0.276015 0.765134 0.100*
H51B 0.699751 0.216552 0.834778 0.100*
H51C 0.691937 0.212340 0.726669 0.100*
C52 0.87404 (12) 0.42957 (10) 0.79436 (13) 0.0439 (4)
C53 0.90029 (14) 0.45110 (12) 0.72398 (17) 0.0607 (6)
H53 0.921874 0.422078 0.693061 0.073*
C54 0.89453 (17) 0.51588 (14) 0.6993 (2) 0.0786 (8)
H54 0.912919 0.529947 0.652475 0.094*
C55 0.86205 (18) 0.55944 (13) 0.7433 (2) 0.0771 (7)
H55 0.858818 0.602803 0.726703 0.093*
C56 0.83443 (18) 0.53852 (12) 0.81182 (18) 0.0706 (7)
H56 0.812592 0.567794 0.842117 0.085*
C57 0.83897 (15) 0.47399 (11) 0.83599 (15) 0.0578 (5)
H57 0.818240 0.460048 0.880828 0.069*
C58 1.05683 (13) 0.27752 (10) 0.59236 (14) 0.0496 (5)
C59 1.11143 (15) 0.24678 (13) 0.56110 (17) 0.0635 (6)
H59 1.127636 0.204675 0.580478 0.076*
C60 1.14202 (18) 0.27870 (18) 0.5009 (2) 0.0813 (9)
H60 1.178443 0.257886 0.479838 0.098*
C61 1.1186 (2) 0.34059 (19) 0.47263 (19) 0.0916 (10)
H61 1.139330 0.361902 0.432608 0.110*
C62 1.0648 (2) 0.37138 (16) 0.50287 (19) 0.0831 (9)
H62 1.048891 0.413458 0.482996 0.100*
C63 1.03398 (16) 0.34053 (12) 0.56257 (16) 0.0636 (6)
H63 0.997649 0.361973 0.583081 0.076*
C64 0.89527 (18) 0.08669 (12) 0.58934 (19) 0.0705 (7)
H64Aa 0.908291 0.085711 0.532875 0.106*
H64Ba 0.913944 0.047643 0.625927 0.106*
H64Ca 0.836771 0.090570 0.569054 0.106*
H64Da 0.864380 0.063571 0.619029 0.106*
H64Ea 0.858727 0.101640 0.525978 0.106*
H64Fa 0.935900 0.058713 0.582850 0.106*

  1. aOccupancy: 0.5.

1 Source of material

The brick-red free diphenyl macrocycle, (I), was prepared employing the same procedure described in a recent study [5] using benzoyl acetone (2.592 g) instead of 2,4-pentanedione. Suitable crystals for the X-ray crystallographic study were prepared by the slow evaporation of the solution of (I) in a solvent mixture of chloroform and xylene in the ratio of 1:1. X-ray crystallography proved the structure to be a known compound [6, 7].

2 Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.93–0.96 Å) and refined as riding with U iso(H) = 1.2–1.5 U eq(C). The N-bound H atom was located in a difference map and refined with N–H = 0.86 ± 0.01 Å. The hydrogen atoms of three methyl groups, i.e. the C19-, C32- and C64-methyl groups, were modelled over two positions of equal weight and rotated 60° to each other. A number of reflections were omitted from the final cycles of refinement owing to poor agreement; see the CIF for details.

3 Comment

The crystal structure of the title macrocycle, (I), has been reported previously [6]; the molecule has also been characterised crystallographically as its 1:1 1,2-dichloroethane solvate [7]. In a recent study, the crystal structure [8] of the all methyl derivative of (I) was re-investigated [5]. The new data allowed a definitive analysis of the nature of the bonding in the N=C–C(H) = C–N(H) residue. The improved data reported here for (I) has similarly allowed a resolution of the bonding in the four N=C–C(H)–C–N(H) residues in the two independent molecules of (I).

Two independent molecules comprise the crystallographic asymmetric-unit of (I); their molecular structures are shown in the figure (35 % probability ellipsoids). To a first approximation, the molecular conformations of the independent molecules are equivalent (see below). The four nitrogen atoms define an approximate plane and feature intramolecular secondary-amine–N–H···N(imine) hydrogen bonds [N1–H1n···N2: H1n···N2 = 1.94(2) Å, N1···N2 = 2.680(3) Å with angle at H1n =  143 ( 2 ) ° ; N3–H3n···N4: H3n···N4 = 1.97(2) Å, N3···N4 = 2.698(3) Å with angle at H3n =  142.3 ( 18 ) ° ; N5–H5n···N6: H5n···N6 = 1.92(2) Å, N5···N6 = 2.665(3) Å with angle at H5n =  145 ( 2 ) ° ; and N7–H7n···N8: H7n···N8 = 2.02(2) Å, N7···N8 = 2.708(3) Å with angle at H7n =  136 ( 2 ) ° ] which close six-membered {···NC3NH} synthons. When viewed side-on through the N4 plane, the N-bound phenyl rings and the two methyl substituents lie to one side of the plane and the remaining chemistry lies to the other side of the plane. Thus, the molecule has the shape of a flattened bowl.

An overlay diagram of the N1-containing molecule (red image) and the inverse of the N5-containing molecule (blue image) is included as an insert in the figure. This diagram illustrates the closeness in conformation between the independent molecules. The differences between the molecules are not chemically significant and are best illustrated by the sequence of C4–C9/C13–C14 [ 44.06 ( 12 ) ° cf. 50.62 ( 11 ) ° for the equivalent angle in the N5-containing molecule], C4–C9/C20–C25 [ 63.02 ( 13 ) ° cf. 59.86 ( 11 ) ° ], C4–C9/C26–C31 [ 64.99 ( 14 ) ° cf. 65.34 ( 13 ) ° ], C13–C14/C20–C25 [ 21.56 ( 13 ) ° cf. 10.43 ( 13 ) ° ], C13–C14/C26–C31 [ 28.54 ( 14 ) ° cf. 17.27 ( 13 ) ° ] and C20–C25/C26–C31 [ 33.34 ( 15 ) ° cf. 15.73 ( 13 ) ° ] dihedral angles.

Considerable delocalisation of π-electron density is noted in the formally N=C–C(H)=C–N(H) residues. Using the C14–N1(H)–C1–C2–C3=N2–C4 sequence as an example for the three remaining residues, the C3=N2 bond of 1.318(3) Å is consistent with a formal double bond. However, the experimentally equivalent C1–C2 and C2–C3 bond lengths, at 1.395(3) and 1.411(3) Å, respectively, are longer and shorter than formal double and single bonds, respectively. Further, the C1–N1 bond is shorter, at 1.337(3) Å, than that expected for a C–N single bond. The delocalisation extends to the fused six-membered rings as seen in the C4–N2 and C14–N1 bond lengths of 1.412(3) and 1.408(3) Å, respectively. Thus, with the possible exception of the C3=N2 bond, the bonding in the remaining atoms of the C14–N1(H)–C1–C2–C3=N2–C4 sequence more closely resembles the bonding, i.e. with extensive delocalisation of π-electron density over this residue, when doubly-deprotonated (I) complexes to M = copper(II) [9] and M = nickel(II) [10], defining square-planar MN4 geometries.

A search for directional interactions in the crystal of (I), with the aid of PLATON [11], only revealed a weak N-bound-phenyl–C–H···π(terminal phenyl) [C16–H16···Cg(C52–C57) i : H16···Cg(C52–C57) i  = 2.96 Å, C16···Cg(C52–C57) i  = 3.723(3) Å and angle at H16 = 140° for symmetry operation (i): x, 1/2 − y, 1/2 + z] contact. These interactions occur between the independent molecules within a helical arrangement of molecules along the b-axis. This conclusion is supported by an analysis of the calculated Hirshfeld surfaces. Thus, with the program suite CrystalExplorer [12] and following standard procedures [13], the surface contacts were evaluated. Previous work [14] has shown how useful such an approach can be in distinguishing independent molecules in a crystal and how these results can confirm space group assignment.

The analysis of surface contacts in (I) indicates shows that 64.1 % of all surface contacts are due to H···H contacts. These are complimented by contributions by C···H/H···C [29.9 %] and N···H/N···N [4.0 %] along with very small contributions from C···C [1.5 %] and N···C/C···N [0.6 %] contacts. In terms of the individual molecules, the nature of the surface contacts closely resemble each other. The greatest difference is noted for H···H contacts where, for the N1-containing molecule, these account for 61.8 % of contacts which is less than 63.1 % for the N5-containing molecule. Smaller differences are noted for the C···H/H···C [32.0 % cf. 31.0 %] and N···H/N···N [4.7 % cf. 3.0 % contacts].

Corresponding author: Edward R. T. Tiekink, Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia, E-mail: . Tapashi Ghosh Roy, Department of Chemistry, Faculty of Science, University of Chittagong, Chattogram 4331, Bangladesh, E-mail: . Ismail M. M. Rahman, Institute of Environmental Radioactivity, Fukushima University, 1 Kanayagawa, Fukushima City, Fukushima 960–1296, Japan, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by grants from the Environmental Radioactivity Research Network Center (ERAN: I-23–13 and I-23–15) and Grants-in–Aid for Scientific Research (21K12287) from the Japan Society for the Promotion of Science (JSPS).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2023-03-27
Accepted: 2023-04-14
Published Online: 2023-05-01
Published in Print: 2023-08-28

© 2023 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  3. Crystal structure of a polymorph of potassium picrate, C6H2KN3O7
  4. The crystal structure of (1E,2E)-1,2-bis(quinolin-2-ylmethylene)hydrazine, C20H14N4
  5. 5-Amino-2-chloro-4-fluoro-N-(N-isopropyl-N-methylsulfamoyl) benzamide, C11H15O3ClFN3S
  6. Crystal structure of trans-N 1,N 8-bis(2-cyanoethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H42N6
  7. The crystal structure of [N-{[2-(oxy)-4-methoxyphenyl](phenyl)methylidene}alaninato]-diphenyl-silicon(IV) – chloroform (1/1), C29H25NO4Si·CHCl3
  8. Crystal structure of tetracarbonyl-{μ-[N-(diphenylphosphanyl)-N,P,P-triphenylphosphinous amide]}-bis[μ-(phenylmethanethiolato)]diiron (Fe–Fe), C48H39Fe2NO4P2S2
  9. Crystal structure of baryte from Mine du Pradet (France)
  10. The crystal structure of [(2,2′-bipyridine-6-carboxylato-κ3 N,N,O)-(6-phenylpyridine-2-carboxylate-κ2 N,O)copper(II)] monohydrate, C23H17N3O5Cu
  11. Crystal structure of bis(μ-benzeneselenolato)-(μ-[N-benzyl-N-(diphenylphosphanyl)-P,P-diphenylphosphinous amide])-tetracarbonyl diiron (Fe–Fe), C47H37Fe2NO4P2Se2
  12. The crystal structure of diaqua-methanol-κ1 O- (3-thiophenecarboxylato-κO)-(2,2′-dipyridyl-κ2 N,N′)manganese(II) 3-thiophenecarboxylate, C21H22N2O7S2Mn
  13. Crystal structure of catena-poly[tetrakis(butyl)-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O:O,O′,N-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O,N,O′:N′-ditin(IV)], C34H50N6O6Sn2
  14. Crystal structure of 4-chloro-N′-[(1E)-(2-nitrophenyl)methylidene]benzohydrazide, C14H10ClN3O3
  15. The crystal structure of 3-(1′-deoxy-3′,5′-O-dibenzy-β-d-ribosyl)adenine dichloromethane solvate, C49H52Cl2N10O6
  16. The crystal structure of (Z)-4-amino-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H17N3O
  17. The co-crystal structure of etoricoxib–phthalic acid (1/1), C18H15ClN2O2S·C8H6O4
  18. Crystal structure of (glycinto-κ 2 O,N ′)-[5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ 4 N,N ′,N ″,N ‴]nickel(II) perchlorate monohydrate C18H42ClN5NiO7
  19. The crystal structure of catena-poly[bis(1-ethylimidazole-k1 N)-(μ 2-benzene-1-carboxyl-3,5-dicarboxylato-κ 2 O, O′)zinc(II)], C19H20N4O6Zn
  20. Crystal structure of 3-(thiazol-2-ylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C11H12N2O4S
  21. Rietveld structure analysis of keatite, a rare, metastable SiO2 polymorph
  22. Crystal structure of catena-poly[(μ2-isophthalato-k3 O,O′:O″)(4-(4-pyridyl)-2,5-dipyrazylpyridine-k3 N,N′,N″)cobalt(II)] trihydrate C26H22N6O7Co1
  23. Crystal structure of 3,5–di-O-benzoyl-1,2-O-isopropylidene-α–D-ribose, C22H22O7
  24. The crystal structure of fac-tricarbonyl(6-bromo-2,2-bipyridine-κ2 N,N)-(nitrato-κO)rhenium(I), C13H7BrN3O6Re
  25. The crystal structure of (E)-N′-(4-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide monohydrate, C19H18N2O4
  26. The crystal structure of 5,5′-diselanediyl-bis(2-hydroxybenzaldehyde), C14H10O4Se2
  27. The crystal structure of catena-poly[diaqua-m2-dicyanido-κ2 C:N-dicyanido-κ1 C-bis(4-(pyridin-4-yl)benzaldehyde-κ1N)iron(II)-platinum(II), C28H22N6O4PtFe
  28. Redetermination of the crystal structure of 5,14-dihydro-6,17-dimethyl-8,15-diphenyldibenzo(b,i)(1,4,8,11)tetra-azacyclotetradecine, C32H28N4
  29. Crystal structure of poly[(μ3-2-(3,5-dicarboxyphenyl) benzimidazole-6-carboxylato-κ4O:O:O′:O″)lead(II)] monohydrate, C16H10N2O7Pb
  30. The crystal structure of fac-tricarbonyl(2-pyridin-2-yl-quinoline-κ2 N,N′)-(pyrazole-κN)rhenium(I)nitrate, C20H14N4O3ReNO3
  31. Crystal structure of dibromo-dicarbonyl-bis(tricyclohexylphosphine)-osmium(II) dichloromethane solvate, C38H66Br2O2OsP2
  32. Crystal structure of poly[bis(μ 2-2,6-bis(1-imidazoly)pyridine-κ 2 N:N′)copper(II)] diperchlorate dihydrate, C22H22Cl2CuN10O10
  33. The crystal structure of fac-tricarbonyl(N-benzoyl-N,N-cyclohexylmethylcarbamimidothioato-κ2 S,O)-(pyridine-κN)rhenium(I), C23H24N3O4ReS
  34. Crystal structure of (E)-7-fluoro-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O
  35. Synthesis and crystal structure of 1-((3R,10S,13S, 17S)-3-((2-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO2
  36. The crystal structure of fac-tricarbonyl((pyridin-2-yl)methanamino-κ2 N,N′)-((pyridin-2-yl)methanamino-κN)rhenium(I) nitrate, C15H16O3N4Re
  37. The crystal structure of (1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)-N-((1-(4-vinylbenzyl)-1H-benzo[d]imidazol-2-yl)methyl)methanamine-κ 4 N,N′,N″,N‴)tris(nitrato-kO,O′)-erbium(III), C29H27ErN8O9
  38. Crystal structure of tetracene-5,12-dione, C18H10O2
  39. Crystal structure of (3R,3aS,6R,6aR)-6-hexyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione, C13H20O4
  40. The crystal structure of N′1,N′3-bis((E)-thiophen-2-ylmethylene)isophthalohydrazide monohydrate, C18H16N4O3S2
  41. Crystal structure of methyl ((4-aminobenzyl)sulfonyl)-L-prolinate, C13H18N2O4S
  42. Crystal structure of (E)-3-(3-methoxybenzylidene)benzofuran-2(3H)-one, C16H12O3
  43. Synthesis and crystal structure (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C11H12BrNO2
  44. Synthesis and crystal structure of (S,E)-4-hydroxy-3-(2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C23H34O5
  45. The crystal structure of N,N′-(1,2-phenylene)bis (2-((2-oxopropyl)selanyl)benzamide), C26H24N2O4Se2
  46. The crystal structure of 1-ethyl-2-nitro-imidazole oxide, C5H7N3O3
  47. The crystal structure of 2-(2-fluorophenyl)naphtho[2,1-d]thiazole, C17H10FNS
  48. Crystal structure of (E)-2,4-di-tert-butyl-6-(((2-fluorophenyl)imino) methyl)phenol, C21H26FNO
  49. Synthesis and crystal structure of 3-methyl-2-(methylthio)-4H-chromen-4-one, C12H12O2S
  50. Crystal structure of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione, C14H4O2S4
  51. The crystal structure of dimethyl 2,2ʹ-((adamantane-1,3-diylbis(4,1-phenylene)) bis(oxy))diacetate, C28H32O6
  52. The crystal structure of N-(6-chloro-2-methyl-2H-indazol-5-yl)acetamide, C10H10ClN3O
  53. Crystal structure of triaqua-(5-bromoisophthalato-κ1 O)-(2,2′-bipyridine-κ2 N:N′)nickel(II) hydrate, C18H19BrN2NiO8
  54. The crystal structure of 2-amino-4-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  55. The crystal structure of catena-poly[5-aminonicotinic acid-k1 N-m2-bromido-copper(I)], Cu(C6N2H6O2)Br
  56. The crystal structure of 2,2-bis(3-methoxyphenyl)-1-tosyl-1,2-dihydro- 2λ4,3λ4  -[1,3,2]diazaborolo[4,5,1-ij]quinoline - dichloromethane (1/1)
  57. The crystal structure of catena-poly[bis(6-phenylpyridine-2-carboxylato-κ2 N,O)-(μ2-4,4′-bipyridne-κ2 N:N)cadmium(II)], C34H24N4O4Cd
  58. The crystal structure of 5,7-dinitropyrazolo[5,1-b]quinazolin-9(4H)-one, C10H5N5O5
  59. Crystal structure of rac-1,8-bis(2-carbamoylethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H46N6O2
  60. The crystal structure of (E)-N ′-(2-bromobenzylidene)-2-naphthohydrazide, C36H26Br2N4O2
  61. The crystal structure of 5-nitronaphthoquinone, C10H5NO4
  62. The crystal structure of (S, R p )-4–benzhydrylideneamino-12-(4-tert-butyl oxazolin-2-yl)[2.2]paracyclophane, C36H36N2O
  63. Synthesis and crystal structure of 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
  64. Crystal structure of 2-(thiazol-2-yl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C11H10N2O3S
  65. Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
  66. Crystal structure of poly[(μ3-3, 5-dichloro-2-hydroxy-benzoato-κ4 Cl,O:O′:O″) silver(I)], C7H3AgCl2O3
  67. The crystal structure of tetrakis(1-isopropylimidazole-κ1 N)-[μ2- imidazole-4,5-dicarboxylato-κ4 O,N,O′,N′)]- trioxido-divanadium, C29H41N10O7V2
  68. Crystal structure of catena-[(μ3-bromido)-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N)copper(I)], C9H7BrCuN3O2
  69. The crystal structure of (E)-4-fluoro-N′-(1-(2-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
https://doi.org/10.1515/ncrs-2023-0146
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of a polymorph of potassium picrate, C6H2KN3O7
  4. The crystal structure of (1E,2E)-1,2-bis(quinolin-2-ylmethylene)hydrazine, C20H14N4
  5. 5-Amino-2-chloro-4-fluoro-N-(N-isopropyl-N-methylsulfamoyl) benzamide, C11H15O3ClFN3S
  6. Crystal structure of trans-N 1,N 8-bis(2-cyanoethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H42N6
  7. The crystal structure of [N-{[2-(oxy)-4-methoxyphenyl](phenyl)methylidene}alaninato]-diphenyl-silicon(IV) – chloroform (1/1), C29H25NO4Si·CHCl3
  8. Crystal structure of tetracarbonyl-{μ-[N-(diphenylphosphanyl)-N,P,P-triphenylphosphinous amide]}-bis[μ-(phenylmethanethiolato)]diiron (Fe–Fe), C48H39Fe2NO4P2S2
  9. Crystal structure of baryte from Mine du Pradet (France)
  10. The crystal structure of [(2,2′-bipyridine-6-carboxylato-κ3 N,N,O)-(6-phenylpyridine-2-carboxylate-κ2 N,O)copper(II)] monohydrate, C23H17N3O5Cu
  11. Crystal structure of bis(μ-benzeneselenolato)-(μ-[N-benzyl-N-(diphenylphosphanyl)-P,P-diphenylphosphinous amide])-tetracarbonyl diiron (Fe–Fe), C47H37Fe2NO4P2Se2
  12. The crystal structure of diaqua-methanol-κ1 O- (3-thiophenecarboxylato-κO)-(2,2′-dipyridyl-κ2 N,N′)manganese(II) 3-thiophenecarboxylate, C21H22N2O7S2Mn
  13. Crystal structure of catena-poly[tetrakis(butyl)-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O:O,O′,N-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O,N,O′:N′-ditin(IV)], C34H50N6O6Sn2
  14. Crystal structure of 4-chloro-N′-[(1E)-(2-nitrophenyl)methylidene]benzohydrazide, C14H10ClN3O3
  15. The crystal structure of 3-(1′-deoxy-3′,5′-O-dibenzy-β-d-ribosyl)adenine dichloromethane solvate, C49H52Cl2N10O6
  16. The crystal structure of (Z)-4-amino-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H17N3O
  17. The co-crystal structure of etoricoxib–phthalic acid (1/1), C18H15ClN2O2S·C8H6O4
  18. Crystal structure of (glycinto-κ 2 O,N ′)-[5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ 4 N,N ′,N ″,N ‴]nickel(II) perchlorate monohydrate C18H42ClN5NiO7
  19. The crystal structure of catena-poly[bis(1-ethylimidazole-k1 N)-(μ 2-benzene-1-carboxyl-3,5-dicarboxylato-κ 2 O, O′)zinc(II)], C19H20N4O6Zn
  20. Crystal structure of 3-(thiazol-2-ylcarbamoyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C11H12N2O4S
  21. Rietveld structure analysis of keatite, a rare, metastable SiO2 polymorph
  22. Crystal structure of catena-poly[(μ2-isophthalato-k3 O,O′:O″)(4-(4-pyridyl)-2,5-dipyrazylpyridine-k3 N,N′,N″)cobalt(II)] trihydrate C26H22N6O7Co1
  23. Crystal structure of 3,5–di-O-benzoyl-1,2-O-isopropylidene-α–D-ribose, C22H22O7
  24. The crystal structure of fac-tricarbonyl(6-bromo-2,2-bipyridine-κ2 N,N)-(nitrato-κO)rhenium(I), C13H7BrN3O6Re
  25. The crystal structure of (E)-N′-(4-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide monohydrate, C19H18N2O4
  26. The crystal structure of 5,5′-diselanediyl-bis(2-hydroxybenzaldehyde), C14H10O4Se2
  27. The crystal structure of catena-poly[diaqua-m2-dicyanido-κ2 C:N-dicyanido-κ1 C-bis(4-(pyridin-4-yl)benzaldehyde-κ1N)iron(II)-platinum(II), C28H22N6O4PtFe
  28. Redetermination of the crystal structure of 5,14-dihydro-6,17-dimethyl-8,15-diphenyldibenzo(b,i)(1,4,8,11)tetra-azacyclotetradecine, C32H28N4
  29. Crystal structure of poly[(μ3-2-(3,5-dicarboxyphenyl) benzimidazole-6-carboxylato-κ4O:O:O′:O″)lead(II)] monohydrate, C16H10N2O7Pb
  30. The crystal structure of fac-tricarbonyl(2-pyridin-2-yl-quinoline-κ2 N,N′)-(pyrazole-κN)rhenium(I)nitrate, C20H14N4O3ReNO3
  31. Crystal structure of dibromo-dicarbonyl-bis(tricyclohexylphosphine)-osmium(II) dichloromethane solvate, C38H66Br2O2OsP2
  32. Crystal structure of poly[bis(μ 2-2,6-bis(1-imidazoly)pyridine-κ 2 N:N′)copper(II)] diperchlorate dihydrate, C22H22Cl2CuN10O10
  33. The crystal structure of fac-tricarbonyl(N-benzoyl-N,N-cyclohexylmethylcarbamimidothioato-κ2 S,O)-(pyridine-κN)rhenium(I), C23H24N3O4ReS
  34. Crystal structure of (E)-7-fluoro-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O
  35. Synthesis and crystal structure of 1-((3R,10S,13S, 17S)-3-((2-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO2
  36. The crystal structure of fac-tricarbonyl((pyridin-2-yl)methanamino-κ2 N,N′)-((pyridin-2-yl)methanamino-κN)rhenium(I) nitrate, C15H16O3N4Re
  37. The crystal structure of (1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)-N-((1-(4-vinylbenzyl)-1H-benzo[d]imidazol-2-yl)methyl)methanamine-κ 4 N,N′,N″,N‴)tris(nitrato-kO,O′)-erbium(III), C29H27ErN8O9
  38. Crystal structure of tetracene-5,12-dione, C18H10O2
  39. Crystal structure of (3R,3aS,6R,6aR)-6-hexyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione, C13H20O4
  40. The crystal structure of N′1,N′3-bis((E)-thiophen-2-ylmethylene)isophthalohydrazide monohydrate, C18H16N4O3S2
  41. Crystal structure of methyl ((4-aminobenzyl)sulfonyl)-L-prolinate, C13H18N2O4S
  42. Crystal structure of (E)-3-(3-methoxybenzylidene)benzofuran-2(3H)-one, C16H12O3
  43. Synthesis and crystal structure (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C11H12BrNO2
  44. Synthesis and crystal structure of (S,E)-4-hydroxy-3-(2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethylidene)dihydrofuran-2(3H)-one, C23H34O5
  45. The crystal structure of N,N′-(1,2-phenylene)bis (2-((2-oxopropyl)selanyl)benzamide), C26H24N2O4Se2
  46. The crystal structure of 1-ethyl-2-nitro-imidazole oxide, C5H7N3O3
  47. The crystal structure of 2-(2-fluorophenyl)naphtho[2,1-d]thiazole, C17H10FNS
  48. Crystal structure of (E)-2,4-di-tert-butyl-6-(((2-fluorophenyl)imino) methyl)phenol, C21H26FNO
  49. Synthesis and crystal structure of 3-methyl-2-(methylthio)-4H-chromen-4-one, C12H12O2S
  50. Crystal structure of dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene-5,10-dione, C14H4O2S4
  51. The crystal structure of dimethyl 2,2ʹ-((adamantane-1,3-diylbis(4,1-phenylene)) bis(oxy))diacetate, C28H32O6
  52. The crystal structure of N-(6-chloro-2-methyl-2H-indazol-5-yl)acetamide, C10H10ClN3O
  53. Crystal structure of triaqua-(5-bromoisophthalato-κ1 O)-(2,2′-bipyridine-κ2 N:N′)nickel(II) hydrate, C18H19BrN2NiO8
  54. The crystal structure of 2-amino-4-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  55. The crystal structure of catena-poly[5-aminonicotinic acid-k1 N-m2-bromido-copper(I)], Cu(C6N2H6O2)Br
  56. The crystal structure of 2,2-bis(3-methoxyphenyl)-1-tosyl-1,2-dihydro- 2λ4,3λ4  -[1,3,2]diazaborolo[4,5,1-ij]quinoline - dichloromethane (1/1)
  57. The crystal structure of catena-poly[bis(6-phenylpyridine-2-carboxylato-κ2 N,O)-(μ2-4,4′-bipyridne-κ2 N:N)cadmium(II)], C34H24N4O4Cd
  58. The crystal structure of 5,7-dinitropyrazolo[5,1-b]quinazolin-9(4H)-one, C10H5N5O5
  59. Crystal structure of rac-1,8-bis(2-carbamoylethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H46N6O2
  60. The crystal structure of (E)-N ′-(2-bromobenzylidene)-2-naphthohydrazide, C36H26Br2N4O2
  61. The crystal structure of 5-nitronaphthoquinone, C10H5NO4
  62. The crystal structure of (S, R p )-4–benzhydrylideneamino-12-(4-tert-butyl oxazolin-2-yl)[2.2]paracyclophane, C36H36N2O
  63. Synthesis and crystal structure of 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
  64. Crystal structure of 2-(thiazol-2-yl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C11H10N2O3S
  65. Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
  66. Crystal structure of poly[(μ3-3, 5-dichloro-2-hydroxy-benzoato-κ4 Cl,O:O′:O″) silver(I)], C7H3AgCl2O3
  67. The crystal structure of tetrakis(1-isopropylimidazole-κ1 N)-[μ2- imidazole-4,5-dicarboxylato-κ4 O,N,O′,N′)]- trioxido-divanadium, C29H41N10O7V2
  68. Crystal structure of catena-[(μ3-bromido)-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N)copper(I)], C9H7BrCuN3O2
  69. The crystal structure of (E)-4-fluoro-N′-(1-(2-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
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