Home Crystal structure of (E)-7-bromo-2-(4-(4-methylpiperazin-1-yl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23BrN2O
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Crystal structure of (E)-7-bromo-2-(4-(4-methylpiperazin-1-yl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23BrN2O

  • Qin-Bing Qi , Wen-Xuan Li , Gui-Ge Hou ORCID logo and Cheng-Bo Li EMAIL logo
Published/Copyright: January 24, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 2

Abstract

C22H23BrN2O, triclinic, P 1 ‾ (no. 2), a = 10.0543(1) Å, b = 11.4893(1) Å, c = 16.5853(1) Å, α = 93.152(1)°, β = 91.877(1)°, γ = 97.097(1)°, V = 1896.81(3) Å3, Z = 4, Rgt(F) = 0.0318, wRref(F2) = 0.0840, T = 293 K.

CCDC no.: 2213155

The asymmetric unit of the title crystal structure is shown in the figure. Displacement ellipsoids are drawn at the 30% probability level. 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: Yellow block
Size: 0.15 × 0.12 × 0.10 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 3.05 mm−1
Diffractometer, scan mode: XtaLAB AFC12 (RINC)
θmax, completeness: 71.6°, 99%
N(hkl)measured, N(hkl)unique, Rint: 19,658, 7178, 0.019
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 6731
N(param)refined: 509
Programs: CrysAlisPRO [1], SHELX [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
Br1 0.55109 (3) 1.18181 (3) 0.02866 (2) 0.05807 (10)
Br2 0.98301 (3) −0.33930 (2) 1.00966 (2) 0.04605 (9)
C1 0.65254 (17) 0.91681 (15) 0.27152 (11) 0.0258 (4)
C2 0.61538 (17) 0.86870 (15) 0.35041 (10) 0.0242 (3)
C3 0.48203 (18) 0.89444 (16) 0.38236 (11) 0.0278 (4)
H3A 0.477650 0.876015 0.438667 0.033*
H3B 0.409750 0.845210 0.352255 0.033*
C4 0.46444 (18) 1.02330 (16) 0.37466 (11) 0.0279 (4)
H4A 0.375762 1.036487 0.391487 0.033*
H4B 0.529869 1.071903 0.410271 0.033*
C5 0.41138 (18) 1.14445 (15) 0.25819 (12) 0.0287 (4)
H5 0.349990 1.178107 0.289899 0.034*
C6 0.43130 (19) 1.18046 (16) 0.18076 (12) 0.0317 (4)
H6 0.384206 1.237978 0.160513 0.038*
C7 0.5224 (2) 1.12948 (17) 0.13400 (12) 0.0342 (4)
C8 0.59297 (19) 1.04367 (17) 0.16270 (12) 0.0315 (4)
H8 0.653526 1.010116 0.130286 0.038*
C9 0.57262 (17) 1.00781 (15) 0.24064 (11) 0.0248 (4)
C10 0.48152 (17) 1.05876 (15) 0.28957 (11) 0.0239 (3)
C11 0.70590 (17) 0.81238 (14) 0.38886 (11) 0.0245 (3)
H11 0.787415 0.812126 0.363954 0.029*
C12 0.69554 (17) 0.75157 (14) 0.46378 (11) 0.0235 (3)
C13 0.81137 (17) 0.74359 (14) 0.51098 (11) 0.0241 (3)
H13 0.893045 0.779068 0.493998 0.029*
C14 0.81014 (17) 0.68541 (15) 0.58170 (11) 0.0250 (4)
H14 0.889597 0.684606 0.611874 0.030*
C15 0.68908 (17) 0.62714 (15) 0.60850 (11) 0.0251 (4)
C16 0.57304 (17) 0.63223 (16) 0.56006 (11) 0.0275 (4)
H16 0.491809 0.593575 0.575349 0.033*
C17 0.57584 (18) 0.69270 (16) 0.49063 (11) 0.0271 (4)
H17 0.496350 0.694616 0.460724 0.032*
C18 0.7992 (2) 0.5779 (2) 0.73218 (13) 0.0414 (5)
H18A 0.836956 0.659919 0.738093 0.050*
H18B 0.864601 0.535397 0.705583 0.050*
C21 0.5734 (2) 0.4857 (3) 0.69326 (18) 0.0707 (10)
H21A 0.578453 0.418691 0.655733 0.085*
H21B 0.493066 0.519253 0.677891 0.085*
C23 0.95557 (18) −0.06368 (16) 0.76427 (11) 0.0270 (4)
C24 0.91578 (17) 0.04370 (15) 0.72836 (11) 0.0250 (4)
C25 0.8890 (2) 0.14180 (16) 0.78761 (11) 0.0308 (4)
H25A 0.844630 0.198734 0.759194 0.037*
H25B 0.973622 0.181329 0.810651 0.037*
C26 0.80134 (19) 0.09647 (16) 0.85566 (11) 0.0293 (4)
H26A 0.799132 0.159607 0.896710 0.035*
H26B 0.710399 0.073599 0.834189 0.035*
C27 0.8179 (2) −0.03271 (18) 0.97274 (12) 0.0329 (4)
H27 0.769151 0.017114 1.002460 0.040*
C28 0.8562 (2) −0.13082 (18) 1.00763 (12) 0.0345 (4)
H28 0.832600 −0.147769 1.059853 0.041*
C29 0.9303 (2) −0.20305 (16) 0.96294 (11) 0.0323 (4)
C30 0.96656 (19) −0.17964 (16) 0.88581 (11) 0.0300 (4)
H30 1.017861 −0.228574 0.857250 0.036*
C31 0.92545 (18) −0.08132 (15) 0.85067 (10) 0.0256 (4)
C32 0.85062 (18) −0.00689 (16) 0.89425 (11) 0.0268 (4)
C33 0.90671 (17) 0.04022 (15) 0.64704 (11) 0.0237 (3)
H33 0.924816 −0.030888 0.623029 0.028*
C34 0.87460 (16) 0.12394 (14) 0.58833 (10) 0.0220 (3)
C35 0.85196 (17) 0.07993 (14) 0.50764 (10) 0.0233 (3)
H35 0.851856 −0.000215 0.496104 0.028*
C36 0.83000 (17) 0.14948 (14) 0.44499 (10) 0.0234 (3)
H36 0.814541 0.115373 0.392837 0.028*
C37 0.83051 (15) 0.27195 (14) 0.45854 (10) 0.0211 (3)
C38 0.84667 (17) 0.31645 (14) 0.53973 (10) 0.0235 (3)
H38 0.842108 0.395852 0.551721 0.028*
C39 0.86916 (17) 0.24485 (15) 0.60212 (10) 0.0242 (3)
H39 0.881005 0.277959 0.654702 0.029*
C40 0.74615 (18) 0.29786 (15) 0.32088 (11) 0.0268 (4)
H40A 0.651304 0.296433 0.330408 0.032*
H40B 0.763227 0.217815 0.307961 0.032*
C41 0.78164 (19) 0.37181 (16) 0.25002 (11) 0.0287 (4)
H41A 0.873826 0.366010 0.236517 0.034*
H41B 0.724365 0.341837 0.203382 0.034*
C42 0.85447 (17) 0.53768 (15) 0.33753 (11) 0.0261 (4)
H42A 0.847342 0.620188 0.349648 0.031*
H42B 0.946332 0.530849 0.323790 0.031*
C43 0.82172 (17) 0.47027 (14) 0.41166 (11) 0.0242 (3)
H43A 0.886430 0.498392 0.455203 0.029*
H43B 0.733480 0.483802 0.429093 0.029*
C44 0.7981 (2) 0.56460 (18) 0.19939 (13) 0.0381 (4)
H44A 0.784488 0.644673 0.212151 0.057*
H44B 0.741262 0.533660 0.153610 0.057*
H44C 0.890217 0.561393 0.186883 0.057*
N1 0.68307 (17) 0.56910 (15) 0.68005 (10) 0.0360 (4)
N3 0.82436 (14) 0.34417 (12) 0.39443 (9) 0.0229 (3)
N4 0.76539 (15) 0.49481 (13) 0.26860 (9) 0.0275 (3)
O1 0.74353 (14) 0.88416 (13) 0.23240 (8) 0.0373 (3)
O2 1.00634 (16) −0.13885 (12) 0.72495 (8) 0.0383 (3)
C19Aa 0.7819 (19) 0.5324 (12) 0.8181 (8) 0.029 (2)
H19Aa 0.867941 0.517453 0.840712 0.034*
H19Ba 0.747554 0.591051 0.853209 0.034*
C20Aa 0.5523 (15) 0.4385 (11) 0.7762 (7) 0.030 (2)
H20Aa 0.511887 0.494453 0.810483 0.036*
H20Ba 0.492372 0.365313 0.771448 0.036*
C22Aa 0.657 (2) 0.3853 (13) 0.8932 (12) 0.056 (3)
H22Aa 0.617403 0.446233 0.921887 0.084*
H22Ba 0.739593 0.373672 0.920605 0.084*
H22Ca 0.596551 0.313586 0.890969 0.084*
N2Aa 0.6838 (3) 0.4187 (3) 0.8122 (2) 0.0253 (7)
C19Ba 0.784 (2) 0.5149 (14) 0.8018 (9) 0.039 (3)
H19Ca 0.819060 0.441234 0.790176 0.047*
H19Da 0.843351 0.558132 0.843288 0.047*
C20Ba 0.5780 (15) 0.4368 (10) 0.7692 (8) 0.039 (4)
H20Ca 0.598050 0.356948 0.759292 0.047*
H20Da 0.487472 0.430909 0.788437 0.047*
C22Ba 0.6623 (19) 0.4215 (13) 0.9087 (11) 0.059 (4)
H22Da 0.688385 0.345148 0.896070 0.089*
H22Ea 0.573048 0.413056 0.928303 0.089*
H22Fa 0.723231 0.462582 0.949415 0.089*
N2Ba 0.6656 (4) 0.4875 (5) 0.8363 (3) 0.0575 (12)

  1. aOccupancy: 0.5.

Source of material

Referring to the literature synthesis [4], 7-bromo-3,4-dihydronaphthalen-1(2H)-one was synthesized with succinic anhydride with the aid of Friedel–Crafts reaction, reduction reaction by hydrazine hydrate, and dehydration condensation. In a round bottom flask, 7-bromo-3,4-dihydronaphthalen-1(2H)-one (0.90 g, 4.00 mmol) and 4-(4-methylpiperazin-1-yl)benzaldehyde (0.82 g, 4.00 mmol) were dissolved in 10 mL of methanol. The mixture stirred in an ice-cold brine bath at 268 K until clarified. Then 5 mL of 25% sodium hydroxide solution was added and the reaction was switched to room temperature and stirred for 1.5 h. The entire reaction was monitored by using thin layer chromatography (TLC). After the reaction, the solvent was removed by filtration, while the filter residue was passed through silica gel column chromatography (dichloromethane: methanol = 40:1), (v/v) to acquire the yellow title compound. The title compound was recrystallized from 30 mL of dichloromethane and 15 mL of methanol at room temperature to get yellow crystals, (E)-7-bromo-2-(4-(4-methylpiperazin-1-yl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one.

Experimental details

The H atoms were placed in idealized positions and treated as riding on their parent atoms, with d(C–H) = 0.96 Å (methyl), Uiso(H) = 1.5Ueq(C), d(C–H) = 0.97 Å (methylene), Uiso(H) = 1.2Ueq(C), and d(C–H) = 0.93 Å (aromatic), Uiso(H) = 1.2Ueq(C).

Comment

In recent years, some heterocyclic anti-inflammatory agents, such as (E)-4-(4-ethylbenzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one [5], and (E)-7-methoxy-2-(4-methoxy-3-(trifluoromethyl) benzylidene)-3,4-dihydronaphthalen-1(2H)-one [6] have been reported and possessed the positive anti-inflammatory and anti-tumor activities with low toxicity. Some meta–CF3 and para–OMe substituted 3,4-dihydronaphthalen-1(2H)-one (DHN) derivatives showed more potential anti-neuroinflammatory actions through inhibiting the activation of NF-kappaB signaling pathway [7]. In order to study the substituent effect, 7-substitute of DHN was replaced by an electron-withdrawing substitute (–Br), while the 2-aromatic ring was replaced by a great electron-donating substitute, such as 4-(4-methylpiperazin-1-yl)benzylidene group.

Single-crystal structure analysis reveals that there are two DHN molecules in the asymmetric unit (cf. the Figure). Bond lengths and angles are all in the expected ranges [8–11]. The pharmacophore of the title compound is 3,4-dihydronaphthalen-1 (2H)-one, with bromine substitution at the 7th position and 4-methylpiperazine substitution at the 2-aromatic ring. In a molecule, 4-methylpiperazine group has a mixed order structurally. Therefore, the 4-methylpiperazine exhibits two types of “chair” conformation and “boat” conformation [8]. In another molecule, 4-methylpiperazine only exhibits “chair” conformation. Both DHN molecules adopt the E stereochemistry of the olefinic double bond [9, 10]. Bond length of C(2) = C(11) is 1.344(3) Å, while bond length of C(24) = C(33) is 1.347(3) Å. The entire molecule forms a linear structure under the action of the olefin bond. In pharmacophore, two methylene groups affect the molecular coplanarity. So, the 2-aromatic ring and the 3,4-dihydronaphthalen-1(2H)-one moiety are not coplanar with each other, and the dihedral angles are about 56.04(4)° and 34.86(2)°, respecitvely. In addition, some active groups, such as carbonyl, α,β-unsaturated keto, and 4-methylpiperazine of the title compound may contribute to the anti-inflammatory activity.

Corresponding author: Cheng-Bo Li, School of Pharmacy, The Key Laboratory of Prescription Effect and Clinical Evaluation of State Administration of Traditional Chinese Medicine of China, Binzhou Medical University, Yantai, 264003, P. R. China, 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: College Youth Innovation Science and Technology Support Programme of Shandong province (No. 2020KJK003) and Key support projects (inheritance and development of traditional Chinese Medicine) of the State Administration of traditional Chinese medicine.

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

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Received: 2022-12-17
Accepted: 2023-01-10
Published Online: 2023-01-24
Published in Print: 2023-04-25

© 2022 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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  37. Crystal structure of dimethyl 4,4′-(((1R, 2R)-cyclohexane-1,2-diyl)bis(azanediyl))dibenzoate, C22H26N2O4
  38. Crystal structure of dimethyl 4,4′-((4R, 5R)-4,5-diphenylimidazolidine-1,3-diyl)dibenzoate, C31H28N2O4
  39. The crystal structure of 2-(2-bromophenyl)-4-phenylbenzo[b][1,4]oxaphosphinine 4-oxide, C20H14BrO2P
  40. The crystal structure of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one, C18H21NO4
  41. Crystal structure of catena-poly[[μ2-1,3-bis[(1H-imidazol-1- yl)methyl]benzene-N:N′]-(μ2–D–camphorato-O, O′: O″, O‴)cadmium(II)], C48H56Cd2N8O8
  42. Crystal structure of N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide, C18H17BrF3N3S
  43. The crystal structure of cis-Dicyano-bis(2,2′-bipyridine)k2N,N′-chromium(III) hexafluorophosphate, C22H16N6F6PCr
  44. Crystal structure of 4-((6-bromohexyl)oxy)-2-hydroxybenzaldehyde, C13H17BrO3
  45. Crystal structure of hydrazinium methanesulfonate, CH8N2O3S
  46. Crystal structure of 1-(2-iodobenzoyl)-6-methoxy-1H-indole-3-carbaldehyde, C17H12INO3
  47. Crystal structure of bis(acridinium) tetrabromidomanganate(II), C26H20Br4MnN2
  48. The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene)) bis(2-(tert-butyl)phenol), C22H28N2O2
  49. The crystal structure of the cocrystal di-μ2-chlorido-tetramethyl-tetraphenyl-di-μ3-oxido-dichloridotetratin(IV) – diphenyl-methyl-chloridotin(IV)(1/2), C54H58Cl6O2Sn6
  50. Crystal structure of (3a7R,13bR)-3-((1R)-1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3a,11,11,13b-tetramethyl-2,3,3a,4,5,11,11a,12,13,13b-decahydroindeno[5′,4′:4,5] cyclohepta[1,2-c]oxepin-9(1H)-one, C30H40O5
  51. Crystal structure of 1-(4-methoxyphenyl)-2-phenoxyethan-1-one, C15H14O3
  52. Crystal structure of trans-tetrakis(3-phenylpyridine-κN)bis(thiocyanato-κN)nickel(II), C46H36N6NiS2
  53. Crystal structure of sodium catena-poly[bis(thiourea-κ1S)-tetrakis(μ2-thiourea-κ2S,S)tricopper(I)] difumarate, C14H29Cu3N12NaO8S6
  54. Crystal structure of bis(benzylamine-κ1N)-bis((E)-2-methyl-3-phenylacrylato-κ1O)copper(II), C34H36CuN2O4
  55. The crystal structure of 3,4-dihydroxybenzoic acid – 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol – water (1/1/1), C30H36F2N6O9S
  56. Crystal structure of catena-poly[dipyridine-bis(pyridine-2-carboxylato-κ 2 N,O)-bis(μ 2-pyridine-2-carboxylato-κ 2 N,O)-dinickel(II)], C34H26N6Ni2O8
  57. The crystal structure of 1-((1-methyl-1H-1,2,4-triazol-3-yl) methyl)-3-(2,4,5-trifluorobenzyl)-1,3,5-triazinane-2,4,6-trione, C14H11F3N6O3
  58. Crystal structure of (E)-2-((Z)-2-((1S,4R)-3,3-dimethylbicyclo[2.2.1] heptan-2-ylidene)ethylidene)hydrazine-1-carbothioamide, C24H38N6S2
  59. Crystal structure of photochromic 3-(5-(2,5-dimethylthiophen-3-yl)-2,2,3,3,4,4-hexafluorocyclopentyl)-2-methylbenzo[b]-thiophene, C20H14F6S2
  60. Crystal structure of bis(2,5,5,7-tetramethyl-1,4-diazepane-1,4-diium) diaqua-bis(1,2-diaminopropane)copper(II) bis(μ6-oxido)tetrakis(μ3-oxido)-tetradecakis(μ2-oxido)-octaoxido-decavanadium(V) – water (1/4), C24H76CuN8V10O34
  61. Crystal structure of 1,2,3,5,13-pentamethoxy-6,7-dimethyl-1,2,3,4,4a,5,6,7,8,13b-decahydrobenzo[3′,4′]cycloocta[1′,2′:4,5]benzo[1,2-d][1,3]dioxole, C24H30O7
  62. Crystal structure of bis(6-carboxyhexyl)-4,4′-bipyridinium dibromide – 2,6-dihydroxynaphthalene (1/2), C42H46Br2N2O8
  63. Crystal structure of methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H21ClN2O5
  64. Crystal structure of bis(dimethylammonium) poly[{μ4-1,1ʹ-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato)-κ6N4O2}zinc(II)], C22H26N6O8Zn
  65. Crystal structure of 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile, C16H13N3O
  66. Crystal structure of (E)-7-methoxy-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23NO3
  67. The crystal structure of N′1,N′2-bis((E)-3-(tert-butyl)-2-hydroxybenzylidene)oxalohydrazide, C24H30N4O4
  68. The crystal structure of trimethyl 2,2′,2′′-(benzene-1,3,5-triyltris(oxy))triacetate, C15H18O9
  69. Crystal structure of bis(N,N-dimethylformamide-κO)-bis(pyridine-2-carboxylato-κ2N,O)-bis(μ2-pyridine-2-carboxylato-κ2N,O)-dinickel(II), C30H30N6Ni2O10
  70. Crystal structure of bis(μ2-1-pyrenecarboxylato-κ3O,O′:O′)-bis(1-pyrenecarboxylato-κ2O,O′)-(benzimidazole-κ1N)dicadmium(II), C82H48Cd2N4O8
  71. One-pot synthesis and crystal structure of diethyl 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C21H23N5O6
  72. The crystal structure of 1-(2-fluorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carbonitrile, C18H13FN2O2
  73. Crystal structure of bis(trimethylphenylammonium) aqua-oxido-octathiotritungstate, (Me3PhN)2[W3OS8(H2O)]
  74. The crystal structure of trichlorido[N-[(2-oxyphenyl)methylidene]phenylglycinemethylester-κ3O,N,O′]-tin(IV) – methylene chloride (1/1), C16H14Cl3NO3Sn·CH2Cl2
  75. The crystal structure of furan-2,5-diylbis((4-chlorophenyl)methanol), C18H14Cl2O3
  76. The crystal structure of hexalithium decavanadate hexadecahydrate, H32Li6O44V10
  77. Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S
  78. Crystal structure of aqua(μ2-2,2′,2″-((nitrilo)tris(ethane-2,1-diyl(nitrilo)methylylidene))tris (6-ethoxyphenolato))(pentane-2,4-dionato-κ2O,O′)-dinickel(II), C38H48N4Ni2O9
https://doi.org/10.1515/ncrs-2022-0590
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of methyl 2-((4-chloro-2-fluoro-6-((2,2,2-trifluoroethyl) thio)phenoxy)methyl)benzoate, C17H13ClF4O3S
  4. The crystal structure of 3-hydroxy-5-oxo-4-propanoylcyclohex-3-ene-1-carboxylic monohydrate, C10H14O6
  5. Crystal structure of 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile, C20H22N4OS
  6. Crystal structure of 1-(3-bromopropyl)-2-((4-chlorophenoxy)methyl)-4-methyl-1H-benzo[d]imidazole, C18H18BrClN2O
  7. Crystal structure of 2-methoxy-6-[(2-morpholin-4-yl-phenylamino)-methylene]-4-nitro-cyclohexa-2,4-dienone, C18H19N3O5
  8. The crystal structure of 2-(7-(2,3-dimethoxyphenyl)-[1,2,4]triazolo[1,5-a]-pyrimidin-5-yl)-3-methoxyphenol, C20H18N4O4
  9. The crystal structure of 3-(1-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinyl)ethylidene)chroman-2,4-dione dihydrate, C20H22N2O8
  10. Crystal structure of 3,5,7-trimethoxy-3′,4′-methylenedioxy-flavone, C19H16O7
  11. The crystal structure of strictic acid, C20H26O3
  12. Crystal structure of 1,1′-(pyrazine-1,4-diyl)-bis(propan-2-one), C10H14N2O2
  13. The crystal structure of 1-(adamantan-1-yl)-3-(4-chlorophenyl)urea, C17H21ClN2O
  14. The crystal structure of (2R,6′R)-2′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-2′-ene-3,4′-dione, C16H14Cl2O5
  15. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-3-((4-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]-phenanthren-17-yl)ethan-1-one, C28H41NO2
  16. Crystal structure of N-2,6-difluorobenzoyl-N′-[1-(3-chloro-4-methyl-phenyl)-4-cyano-1H-pyrazol-5-carbamoyl]urea, C19H12ClF2N5O2
  17. Crystal structure of (−)-β-D-19-glucopiranosyl-9,15-dihydroxy kaurenoate, C26H40O9
  18. Crystal structure of 7-hydroxy-6-(2-hydroxyethyl)-2H-chromen-2-one, C11H10O4
  19. Crystal structure of S-(benzo[d]thiazol-2-yl)-N-(tert-butyl)thiohydroxylamine, C11H14N2S2
  20. Crystal structure of poly[di-µ2-aqua-aqua-nitrato-κ2O,O′-(µ3-2-nitroisophthalato-κ4O,O′:O″:O′″)barium(II)natrium(II)] monohydrate, C8H11BaN2NaO13
  21. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2 N,O)-cobalt(II) dihydrate, C14H16N6O8Co
  22. Crystal structure of (S,E)-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-4-yl)-2,3- dihydroquinazolin-4(1H)-one monohydrate, C19H15N5O⋅H2O
  23. Synthesis and crystal structure of 5-(8-(((5-carboxypentyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxy-3-nitrobenzenesulfonate monohydrate, C22H24N2O12S
  24. Synthesis and crystal structure of 8-bromo-3-(1H-pyrazole-1-carbonyl)-2H-chromen-2-one, C13H7BrN2O3
  25. Crystal structure of E-7-fluoro-2-(4-methoxy-3-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  26. Hydrogen bonded dimers in the crystal structure of 2-chloro-N-((3,5-dimethylphenyl)carbamoyl)-nicotinamide, C30H28Cl2N6O4
  27. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-allyl-1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C10H12F6N2P
  28. Crystal structure of (E)-7-bromo-2-(4-(4-methylpiperazin-1-yl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23BrN2O
  29. Crystal structure of pentacarbonyl-(μ2-ethane-1,2-dithiolato-κ4S:S,S′:S′)-(diphenyl(o-tolyl)phosphine-κ1P)diiron (Fe–Fe), C26H21Fe2O5PS2
  30. Crystal structure of 9-(2-chloroethoxy)-4-(4-methoxy-3-(trifluoromethyl)phenyl)- 5,6-dihydrobenzo[h]quinazolin-2-amine, C22H19ClF3N3O2
  31. Crystal structure of triaqua-[5-bromo-2-(carboxylatomethoxy)benzoate-κ3 O,O′,O″]nickel(II), C9H11BrNiO8
  32. The crystal structure of 4,4′-dichloro-3,5′-diphenyl-1′H-1,3′- bipyrazole, C18H12Cl2N4
  33. The crystal structure of bis(1H-pyrazole-carboxamidine-κN,N′)bis(nitrato-κO)-copper(II), C8H12CuN10O6
  34. Synthesis and crystal structure of 3-bromo-4-phenyl-2H-chromene, C15H11BrO
  35. Crystal structure of (E)-5-(diethylamino)-2-((morpholinoimino)methyl)phenol, C15H23N3O2
  36. Crystal structure of niobium trigallide, NbGa3
  37. Crystal structure of dimethyl 4,4′-(((1R, 2R)-cyclohexane-1,2-diyl)bis(azanediyl))dibenzoate, C22H26N2O4
  38. Crystal structure of dimethyl 4,4′-((4R, 5R)-4,5-diphenylimidazolidine-1,3-diyl)dibenzoate, C31H28N2O4
  39. The crystal structure of 2-(2-bromophenyl)-4-phenylbenzo[b][1,4]oxaphosphinine 4-oxide, C20H14BrO2P
  40. The crystal structure of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one, C18H21NO4
  41. Crystal structure of catena-poly[[μ2-1,3-bis[(1H-imidazol-1- yl)methyl]benzene-N:N′]-(μ2–D–camphorato-O, O′: O″, O‴)cadmium(II)], C48H56Cd2N8O8
  42. Crystal structure of N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide, C18H17BrF3N3S
  43. The crystal structure of cis-Dicyano-bis(2,2′-bipyridine)k2N,N′-chromium(III) hexafluorophosphate, C22H16N6F6PCr
  44. Crystal structure of 4-((6-bromohexyl)oxy)-2-hydroxybenzaldehyde, C13H17BrO3
  45. Crystal structure of hydrazinium methanesulfonate, CH8N2O3S
  46. Crystal structure of 1-(2-iodobenzoyl)-6-methoxy-1H-indole-3-carbaldehyde, C17H12INO3
  47. Crystal structure of bis(acridinium) tetrabromidomanganate(II), C26H20Br4MnN2
  48. The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene)) bis(2-(tert-butyl)phenol), C22H28N2O2
  49. The crystal structure of the cocrystal di-μ2-chlorido-tetramethyl-tetraphenyl-di-μ3-oxido-dichloridotetratin(IV) – diphenyl-methyl-chloridotin(IV)(1/2), C54H58Cl6O2Sn6
  50. Crystal structure of (3a7R,13bR)-3-((1R)-1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3a,11,11,13b-tetramethyl-2,3,3a,4,5,11,11a,12,13,13b-decahydroindeno[5′,4′:4,5] cyclohepta[1,2-c]oxepin-9(1H)-one, C30H40O5
  51. Crystal structure of 1-(4-methoxyphenyl)-2-phenoxyethan-1-one, C15H14O3
  52. Crystal structure of trans-tetrakis(3-phenylpyridine-κN)bis(thiocyanato-κN)nickel(II), C46H36N6NiS2
  53. Crystal structure of sodium catena-poly[bis(thiourea-κ1S)-tetrakis(μ2-thiourea-κ2S,S)tricopper(I)] difumarate, C14H29Cu3N12NaO8S6
  54. Crystal structure of bis(benzylamine-κ1N)-bis((E)-2-methyl-3-phenylacrylato-κ1O)copper(II), C34H36CuN2O4
  55. The crystal structure of 3,4-dihydroxybenzoic acid – 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol – water (1/1/1), C30H36F2N6O9S
  56. Crystal structure of catena-poly[dipyridine-bis(pyridine-2-carboxylato-κ 2 N,O)-bis(μ 2-pyridine-2-carboxylato-κ 2 N,O)-dinickel(II)], C34H26N6Ni2O8
  57. The crystal structure of 1-((1-methyl-1H-1,2,4-triazol-3-yl) methyl)-3-(2,4,5-trifluorobenzyl)-1,3,5-triazinane-2,4,6-trione, C14H11F3N6O3
  58. Crystal structure of (E)-2-((Z)-2-((1S,4R)-3,3-dimethylbicyclo[2.2.1] heptan-2-ylidene)ethylidene)hydrazine-1-carbothioamide, C24H38N6S2
  59. Crystal structure of photochromic 3-(5-(2,5-dimethylthiophen-3-yl)-2,2,3,3,4,4-hexafluorocyclopentyl)-2-methylbenzo[b]-thiophene, C20H14F6S2
  60. Crystal structure of bis(2,5,5,7-tetramethyl-1,4-diazepane-1,4-diium) diaqua-bis(1,2-diaminopropane)copper(II) bis(μ6-oxido)tetrakis(μ3-oxido)-tetradecakis(μ2-oxido)-octaoxido-decavanadium(V) – water (1/4), C24H76CuN8V10O34
  61. Crystal structure of 1,2,3,5,13-pentamethoxy-6,7-dimethyl-1,2,3,4,4a,5,6,7,8,13b-decahydrobenzo[3′,4′]cycloocta[1′,2′:4,5]benzo[1,2-d][1,3]dioxole, C24H30O7
  62. Crystal structure of bis(6-carboxyhexyl)-4,4′-bipyridinium dibromide – 2,6-dihydroxynaphthalene (1/2), C42H46Br2N2O8
  63. Crystal structure of methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H21ClN2O5
  64. Crystal structure of bis(dimethylammonium) poly[{μ4-1,1ʹ-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato)-κ6N4O2}zinc(II)], C22H26N6O8Zn
  65. Crystal structure of 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile, C16H13N3O
  66. Crystal structure of (E)-7-methoxy-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23NO3
  67. The crystal structure of N′1,N′2-bis((E)-3-(tert-butyl)-2-hydroxybenzylidene)oxalohydrazide, C24H30N4O4
  68. The crystal structure of trimethyl 2,2′,2′′-(benzene-1,3,5-triyltris(oxy))triacetate, C15H18O9
  69. Crystal structure of bis(N,N-dimethylformamide-κO)-bis(pyridine-2-carboxylato-κ2N,O)-bis(μ2-pyridine-2-carboxylato-κ2N,O)-dinickel(II), C30H30N6Ni2O10
  70. Crystal structure of bis(μ2-1-pyrenecarboxylato-κ3O,O′:O′)-bis(1-pyrenecarboxylato-κ2O,O′)-(benzimidazole-κ1N)dicadmium(II), C82H48Cd2N4O8
  71. One-pot synthesis and crystal structure of diethyl 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C21H23N5O6
  72. The crystal structure of 1-(2-fluorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carbonitrile, C18H13FN2O2
  73. Crystal structure of bis(trimethylphenylammonium) aqua-oxido-octathiotritungstate, (Me3PhN)2[W3OS8(H2O)]
  74. The crystal structure of trichlorido[N-[(2-oxyphenyl)methylidene]phenylglycinemethylester-κ3O,N,O′]-tin(IV) – methylene chloride (1/1), C16H14Cl3NO3Sn·CH2Cl2
  75. The crystal structure of furan-2,5-diylbis((4-chlorophenyl)methanol), C18H14Cl2O3
  76. The crystal structure of hexalithium decavanadate hexadecahydrate, H32Li6O44V10
  77. Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S
  78. Crystal structure of aqua(μ2-2,2′,2″-((nitrilo)tris(ethane-2,1-diyl(nitrilo)methylylidene))tris (6-ethoxyphenolato))(pentane-2,4-dionato-κ2O,O′)-dinickel(II), C38H48N4Ni2O9
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