Home The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
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The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3

  • Marcus Herbig ORCID logo and Uwe Böhme ORCID logo EMAIL logo
Published/Copyright: February 22, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 3

Abstract

C10H20BNO3, monoclinic, P21/c (no. 14), a = 11.0681(8) Å, b = 6.1883(3) Å, c = 18.1603(13) Å, β = 105.111(6)°, V = 1200.84(14) Å3, Z = 4, R gt(F) = 0.0338, wR ref(F 2) = 0.0861, T = 153 K.

CCDC no.: 2241072

The molecular structure is shown in the figure. 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: Colourless plate
Size: 0.45 × 0.25 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: STOE IPDS 2T, Omega scan
θ max, completeness: 27.2°, >99%
N(hkl)measured, N(hkl)unique, R int: 14,127, 2663, 0.043
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2235
N(param)refined: 140
Programs: X-Red [1], Shelx [2, 3], Ortep-III [4]
Table 2:

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

Atom x y z U iso*/U eq
B1 0.26364 (11) 0.28816 (19) 0.48106 (7) 0.0234 (2)
O1 0.35529 (7) 0.23210 (13) 0.54606 (4) 0.02751 (19)
O2 0.18477 (7) 0.44944 (12) 0.49341 (4) 0.02599 (18)
C1 0.34902 (10) 0.39470 (18) 0.60321 (6) 0.0268 (2)
C2 0.21010 (10) 0.47318 (17) 0.57596 (6) 0.0248 (2)
C3 0.44204 (12) 0.5722 (2) 0.59845 (8) 0.0391 (3)
H3A 0.525489 0.509092 0.605470 0.059*
H3B 0.444228 0.679558 0.638443 0.059*
H3C 0.416247 0.642113 0.548371 0.059*
C4 0.38405 (12) 0.2889 (2) 0.68126 (7) 0.0375 (3)
H4A 0.332664 0.159548 0.680496 0.056*
H4B 0.369452 0.390741 0.719365 0.056*
H4C 0.472648 0.248115 0.694328 0.056*
C5 0.18759 (13) 0.70723 (19) 0.59385 (7) 0.0354 (3)
H5A 0.240123 0.801645 0.571840 0.053*
H5B 0.208805 0.727580 0.649260 0.053*
H5C 0.099303 0.743467 0.571987 0.053*
C6 0.11912 (11) 0.3267 (2) 0.60222 (7) 0.0315 (3)
H6A 0.033124 0.365720 0.575342 0.047*
H6B 0.130744 0.343934 0.657269 0.047*
H6C 0.134889 0.175989 0.590961 0.047*
N1 0.25101 (8) 0.19277 (15) 0.40961 (5) 0.0260 (2)
C7 0.32938 (10) 0.01700 (18) 0.39482 (6) 0.0287 (2)
H7A 0.388500 −0.028772 0.443184 0.034*
H7B 0.378696 0.067386 0.359821 0.034*
C8 0.24809 (12) −0.17242 (19) 0.35943 (7) 0.0344 (3)
H8A 0.301403 −0.287892 0.346932 0.041*
H8B 0.205397 −0.231453 0.396646 0.041*
O3 0.15666 (8) −0.10884 (14) 0.29171 (5) 0.0361 (2)
C9 0.07691 (11) 0.0550 (2) 0.30894 (7) 0.0324 (3)
H9A 0.032906 −0.002381 0.345761 0.039*
H9B 0.013130 0.095937 0.261815 0.039*
C10 0.15182 (10) 0.25192 (18) 0.34232 (6) 0.0271 (2)
H10A 0.189093 0.317892 0.303686 0.033*
H10B 0.095932 0.359964 0.356573 0.033*

1 Source of materials

In a representative experiment 1.037 g morpholine (11.9 mmol, Sigma–Aldrich, distilled from CaH2) was placed in a 100-ml round bottom flask. About 20 mL of THF (VWR AnalaR Normapur, dried with MBraun SPS 800) and 1.472 g TMEDA (12.7 mmol, Sigma–Aldrich, distilled from CaH2) were added. The solution was cooled in an ice bath and CO2 (Linde, 5.4) was introduced into this solution for 20 min forming a white suspension within 5 min. To this supension 1.874 g HBpin (14.6 mmol, TCI, >97%) was added. A gas evolution took place during the addition and afterwards the solution was heated to about 50 °C for about 1 h. After standing overnight at room temperature, crystals were obtained. All volatiles were removed in vacuo and a white solid was yielded used for further analyses.

NMR (CDCl3, ppm): 11B NMR (160 MHz) δ = 23; 1H NMR (500 MHz) δ = 3.55–3.49 (m, 4H, O–CH2), 3.08–3.02 (m, 4H, N–CH2), 1.20 (s, 12H, CH3); 13 C NMR (125 MHz) δ = 81.7 (C1 and C2), 67.9 (O–CH2), 44.1 (N–CH2), 24.3 (CH3).

IR (cm−1): 2991.2 (w), 2970.0 (w), 2929.5 (vw), 1546.7 (w), 1508.1 (m), 1475.3 (m), 1456.1 (m), 1409.8 (w), 1386.6 (w), 1367.4 (m), 1357.7 (w), 1305.6 (w), 1269.0 (s), 1216.9 (vw), 1151.4 (s), 1124.4 (vw), 1101.2 (vs), 1080.0 (m), 1062.6 (m), 1049.1 (w), 1002.9 (vs), 989.4 (vs), 954.6 (vs), 933.4 (s), 918.0 (m), 875.6 (vs), 865.9 (vs), 840.9 (m), 784.9 (w), 756.0 (vw), 730.9 (w), 705.9 (w), 676.9 (s), 642.2 (w), 603.6 (w).

2 Experimental details

The carbon-bound hydrogen atoms were geometrically placed (C—H = 0.98–0.99 Å) and refined as riding atoms with U iso (H) = 1.2–1.5 U eq (C).

3 Comment

Aminoboranes R2N–BR2 are utilized in a variety of transformations like Strecker type aminative cyanation, Mannich-type reaction, and reductive amination [5, 6 5,6]. Herein we describe the crystal structure of a simple aminoborane formed out of pinacolborane (“HBpin”) and morpholine.

The asymmetric unit contains one molecule of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine. The bond lengths are in the expected ranges. Bond angles in the five membered 1,3,2–dioxaborolane ring are smaller than expected due to the five membered ring, for instance B1—O1—C1 105.85(8)° and B1—O2—C2 106.20(8)°. The planes O1—B1—O2 and C7—N1—-C10 are nearly coplanar, as can be seen from the values of the torsion angles O1—B1—N1—C7 and O2—B1—N1—C10 with 2.38(17)° and −1.39(17)°, respectively. The five membered 1,3,2–dioxaborolane ring is twisted on C1 and C2. These two atoms are 0.1848(6) Å (C1) below and 0.1876(6) Å above the least squares plane of the ring atoms C1—C2—O2—B1—O1. The six membered morpholine ring adopts a chair conformation.

About 70 related crystal structures of aminoboranes containing the 1,3,2–dioxaborolane ring bound to secondary amines are listed in the Cambridge Structural Database [7].

Corresponding author: Uwe Böhme, Institut für Anorganische Chemie Technische, Universität Bergakademie Freiberg, Leipziger Str. 29, 09599 Freiberg, Germany, E-mail:

Funding source: TU Bergakademie Freiberg (Freiberg, Germany) http://dx.doi.org/10.13039/501100021786

  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 funded by TU Bergakademie Freiberg (Freiberg, Germany, https://doi.org/10.13039/501100021786).

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

References

1. Stoe & Cie. X–Red (Version 1.53) and X–Area (Version 1.55); Stoe & Cie GmbH: Darmstadt, Germany, 2009.Search in Google Scholar

2. Sheldrick, G. M. Shelxtl – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M. Crystal structure refinement with Shelxl. Acta Crystallogr. 2015, C71, 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

4. Farrugia, L. J. Ortep-3 for Windows-a version of Ortep–III with a graphical user interface (GUI). J. Appl. Crystallogr. 1997, 30, 565; https://doi.org/10.1107/S0021889897003117.Search in Google Scholar

5. Liptrot, D. J., Hill, M. S., Mahon, M. F., Wilson, A. S. S. Alkaline-earth-catalyzed dehydrocoupling of amines and boranes. Angew. Chem. Int. Ed. 2015, 54, 13362–13365; https://doi.org/10.1002/anie.201505949.Search in Google Scholar PubMed PubMed Central

6. Suginome, M. Aminoboranes as new iminium ion generators in amination reactions. Pure Appl. Chem. 2006, 78, 1377–1387; https://doi.org/10.1351/pac200678071377.Search in Google Scholar

7. Groom, C. R., Bruno, I. J., Lightfoot, M. P., Ward, S. C. The Cambridge structural database. Acta Crystallogr. 2016, B72, 171–179; https://doi.org/10.1107/S2052520616003954.Search in Google Scholar PubMed PubMed Central

Received: 2023-01-17
Accepted: 2023-02-10
Published Online: 2023-02-22
Published in Print: 2023-06-27

© 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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  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
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  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
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https://doi.org/10.1515/ncrs-2023-0030
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,Nʹ,Nʺ]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N′1,N′3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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