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4-[(1-Hydro­xy­cyclo­hexyl)­methyl]-5-(2-hydroxy-1-phenyl­ethyl)-2,2-di­phenyl-1,3-dioxa-4-azonia-2-borata-4-cyclo­pentene benzene hemisolvate, C28H32BNO4·0.5C6H6, contains a five-membered BONCO heterocycle with a B-envelope conformation, formed by the hydro­xamate portion of the mol­ecule. Bond lengths and angles are similar to those in related compounds. The crystal structure contains a mol­ecule of benzene lying on a crystallographic inversion centre. The heterocycle mol­ecules are linked by pairs of O—H...O hydrogen bonds and possible O—H...π-interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018172/cf6214sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018172/cf6214IIsup2.hkl
Contains datablock II

CCDC reference: 200757

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.051
  • wR factor = 0.054
  • Data-to-parameter ratio = 18.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
PLAT_420 Alert B D-H Without Acceptor O(4) - H(4) ?
Author response: See Comment, final paragraph

Yellow Alert Alert Level C:
PLAT_368 Alert C Short C(sp2)-C(sp2) Bond C(30) - C(31) = 1.21 Ang.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Diffractometer Control Software (Enraf-Nonius, 1978); cell refinement: CAD-4 Diffractometer Control Software; data reduction: local programs (Rettig, 1978); program(s) used to solve structure: MULTAN80 (Main et al., 1980); program(s) used to refine structure: ORFLS (Busing et al., 1962); software used to prepare material for publication: TEXSAN (Molecular Structure Corporation, 1989).

(II) top
Crystal data top
C28H32BNO4·0.5C6H6F(000) = 1060
Mr = 496.42Dx = 1.164 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.310 (1) ÅCell parameters from 25 reflections
b = 22.089 (2) Åθ = 15.1–18.9°
c = 10.965 (1) ŵ = 0.08 mm1
β = 108.26 (1)°T = 294 K
V = 2831.4 (5) Å3Prism, colorless
Z = 40.45 × 0.25 × 0.25 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2467 reflections with I > 3σ(I)
Radiation source: X-ray tubeRint = 0.0
Graphite monochromatorθmax = 27.5°, θmin = 0.0°
ω–2θ scansh = 015
Absorption correction: ψ scan
(local program; Rettig, 1978)
k = 028
Tmin = 0.96, Tmax = 0.98l = 1413
6443 measured reflections3 standard reflections every 150 reflections
6443 independent reflections intensity decay: 0.0%
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.054Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.0004Fo2]
S = 1.96(Δ/σ)max = 0.04
6443 reflectionsΔρmax = 0.35 e Å3
342 parametersΔρmin = 0.36 e Å3
Special details top

Experimental. The scan width was (0.95 + 0.35tanθ)° with a variable ω scan speed (1.5–10°/min). Scan time:background time ratio was 2:1. Three standard reflections remained constant in intensity throughout the data collection.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0772 (2)0.1700 (1)0.1423 (2)0.061 (1)
O20.1889 (2)0.0819 (1)0.1973 (2)0.052 (1)
O30.0550 (2)0.1004 (1)0.1830 (2)0.064 (1)
O40.1218 (2)0.0300 (1)0.0071 (3)0.075 (1)
N10.1099 (2)0.1450 (1)0.0435 (2)0.049 (1)
C10.1725 (2)0.0970 (1)0.0794 (3)0.045 (3)
C20.0769 (3)0.1779 (1)0.0776 (3)0.052 (3)
C30.0443 (3)0.1641 (1)0.1630 (3)0.049 (3)
C40.0605 (3)0.1915 (1)0.2954 (3)0.067 (3)
C50.1829 (4)0.1841 (2)0.3831 (3)0.094 (4)
C60.2688 (4)0.2104 (2)0.3251 (5)0.107 (5)
C70.2548 (3)0.1817 (2)0.1956 (4)0.091 (4)
C80.1340 (3)0.1885 (1)0.1067 (3)0.064 (3)
C90.2269 (2)0.0627 (1)0.0043 (3)0.045 (3)
C100.2319 (3)0.0052 (1)0.0274 (3)0.058 (3)
C110.3453 (3)0.0867 (1)0.0096 (3)0.053 (3)
C120.4165 (3)0.1093 (2)0.1245 (3)0.073 (3)
C130.5249 (3)0.1298 (2)0.1335 (4)0.092 (4)
C140.5634 (3)0.1278 (2)0.0304 (5)0.092 (4)
C150.4942 (4)0.1065 (2)0.0829 (4)0.094 (4)
C160.3856 (3)0.0857 (2)0.0942 (3)0.077 (3)
C170.0165 (3)0.0886 (1)0.2813 (3)0.053 (3)
C180.0235 (3)0.0271 (2)0.3070 (3)0.062 (3)
C190.0625 (4)0.0041 (2)0.3371 (3)0.079 (4)
C200.1568 (4)0.0256 (2)0.3428 (4)0.087 (4)
C210.1683 (3)0.0863 (3)0.3171 (4)0.095 (4)
C220.0823 (3)0.1176 (2)0.2864 (4)0.082 (4)
C230.2022 (3)0.1600 (1)0.3779 (3)0.055 (3)
C240.2851 (3)0.1990 (2)0.3635 (3)0.075 (3)
C250.3604 (3)0.2277 (2)0.4671 (4)0.089 (4)
C260.3554 (4)0.2191 (2)0.5878 (4)0.090 (4)
C270.2728 (4)0.1821 (2)0.6052 (3)0.088 (4)
C280.1971 (3)0.1532 (2)0.5015 (3)0.071 (3)
C290.4421 (9)0.4792 (5)0.0751 (11)0.28 (2)
C300.5262 (11)0.4437 (4)0.0519 (12)0.27 (2)
C310.5949 (9)0.4690 (7)0.0111 (12)0.33 (2)
B10.1188 (3)0.1260 (2)0.2563 (3)0.051 (3)
H2a0.08240.22140.05870.065*
H2b0.13010.16740.12440.065*
H30.069 (3)0.0864 (16)0.119 (3)0.083 (13)*
H40.083 (4)0.032 (2)0.074 (5)0.14 (2)*
H4a0.04200.23480.28550.080*
H4b0.00860.17140.33430.080*
H5a0.19060.20460.46460.107*
H5b0.19860.14080.39910.107*
H6a0.25660.25410.31450.120*
H6b0.34610.20250.38270.120*
H7a0.30720.20150.15660.104*
H7b0.27360.13860.20750.104*
H8a0.11880.23160.08760.077*
H8b0.12720.16660.02700.077*
H90.17950.06800.09400.058*
H100.26890.02650.02730.071*
H110.27720.01080.11770.071*
H120.39030.11090.19910.086*
H130.57390.14560.21430.105*
H140.64000.14150.03800.104*
H150.52110.10540.15710.107*
H160.33720.07030.17610.090*
H180.09080.00510.30410.074*
H190.05530.04710.35390.092*
H200.21660.00400.36480.100*
H210.23630.10760.32040.108*
H220.09160.16050.26780.095*
H240.29010.20640.27840.088*
H250.41820.25430.45420.102*
H260.40930.23890.66060.102*
H270.26700.17620.69060.101*
H280.13860.12730.51560.084*
H290.41000.47030.14280.29*
H300.52970.40060.06750.28*
H310.67330.45510.03560.34*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.085 (2)0.049 (1)0.059 (1)0.020 (1)0.035 (1)0.002 (1)
O20.064 (1)0.046 (1)0.051 (1)0.011 (1)0.025 (1)0.005 (1)
O30.092 (2)0.037 (1)0.071 (2)0.006 (1)0.037 (1)0.001 (1)
O40.090 (2)0.066 (2)0.070 (2)0.028 (1)0.027 (1)0.001 (1)
N10.056 (2)0.046 (2)0.053 (1)0.005 (1)0.026 (1)0.003 (1)
C10.045 (2)0.040 (2)0.055 (2)0.002 (1)0.020 (1)0.003 (2)
C20.063 (2)0.040 (2)0.060 (2)0.002 (2)0.029 (2)0.011 (1)
C30.059 (2)0.035 (2)0.054 (2)0.001 (1)0.021 (2)0.004 (1)
C40.079 (3)0.062 (2)0.063 (2)0.007 (2)0.025 (2)0.015 (2)
C50.097 (3)0.099 (3)0.070 (2)0.027 (3)0.001 (2)0.031 (2)
C60.069 (3)0.105 (4)0.128 (4)0.002 (2)0.004 (3)0.035 (3)
C70.061 (3)0.098 (3)0.116 (3)0.002 (2)0.029 (2)0.013 (3)
C80.061 (2)0.056 (2)0.080 (2)0.004 (2)0.031 (2)0.002 (2)
C90.046 (2)0.043 (2)0.049 (2)0.004 (1)0.019 (1)0.000 (1)
C100.071 (2)0.047 (2)0.061 (2)0.004 (2)0.028 (2)0.004 (2)
C110.048 (2)0.048 (2)0.067 (2)0.007 (2)0.026 (2)0.005 (2)
C120.054 (2)0.099 (3)0.069 (2)0.002 (2)0.021 (2)0.008 (2)
C130.056 (2)0.118 (4)0.098 (3)0.005 (2)0.017 (2)0.019 (3)
C140.059 (2)0.092 (3)0.133 (4)0.006 (2)0.044 (3)0.005 (3)
C150.079 (3)0.122 (4)0.102 (3)0.018 (3)0.058 (3)0.013 (3)
C160.066 (2)0.094 (3)0.082 (2)0.013 (2)0.038 (2)0.014 (2)
C170.059 (2)0.057 (2)0.046 (2)0.003 (2)0.019 (2)0.006 (2)
C180.073 (2)0.055 (2)0.065 (2)0.005 (2)0.032 (2)0.005 (2)
C190.094 (3)0.071 (3)0.081 (3)0.023 (2)0.042 (2)0.010 (2)
C200.078 (3)0.110 (4)0.079 (3)0.033 (3)0.033 (2)0.017 (3)
C210.057 (3)0.129 (4)0.107 (3)0.011 (3)0.037 (2)0.009 (3)
C220.069 (3)0.079 (3)0.108 (3)0.016 (2)0.040 (2)0.006 (2)
C230.064 (2)0.044 (2)0.061 (2)0.003 (2)0.027 (2)0.003 (2)
C240.091 (3)0.071 (2)0.073 (2)0.018 (2)0.040 (2)0.009 (2)
C250.087 (3)0.080 (3)0.109 (3)0.027 (2)0.043 (3)0.022 (3)
C260.092 (3)0.087 (3)0.084 (3)0.006 (3)0.019 (2)0.027 (2)
C270.118 (3)0.089 (3)0.059 (2)0.018 (3)0.030 (2)0.011 (2)
C280.091 (3)0.067 (2)0.060 (2)0.016 (2)0.031 (2)0.004 (2)
C290.279 (10)0.268 (11)0.399 (14)0.124 (9)0.257 (11)0.196 (11)
C300.297 (12)0.173 (7)0.468 (17)0.094 (8)0.283 (12)0.134 (9)
C310.226 (10)0.407 (17)0.443 (16)0.192 (11)0.236 (11)0.283 (14)
B10.064 (2)0.042 (2)0.054 (2)0.011 (2)0.027 (2)0.002 (2)
Geometric parameters (Å, º) top
O1—N11.383 (4)C12—H120.97
O1—B11.539 (4)C13—C141.357 (7)
O2—C11.288 (4)C13—H130.97
O2—B11.569 (5)C14—C151.352 (6)
O3—C31.424 (3)C14—H140.97
O3—H30.83 (4)C15—C161.382 (6)
O4—C101.413 (4)C15—H150.97
O4—H40.87 (4)C16—H160.97
N1—C11.297 (3)C17—C181.385 (5)
N1—C21.456 (4)C17—C221.391 (5)
C1—C91.500 (4)C17—B11.600 (5)
C2—C31.523 (4)C18—C191.387 (6)
C2—H2a0.98C18—H180.97
C2—H2b0.98C19—C201.352 (7)
C3—C41.527 (4)C19—H190.97
C3—C81.523 (5)C20—C211.368 (8)
C4—C51.521 (5)C20—H200.97
C4—H4a0.98C21—C221.391 (7)
C4—H4b0.98C21—H210.97
C5—C61.510 (7)C22—H220.97
C5—H5a0.98C23—C241.382 (5)
C5—H5b0.98C23—C281.384 (5)
C6—C71.515 (7)C23—B11.593 (4)
C6—H6a0.98C24—C251.375 (5)
C6—H6b0.98C24—H240.97
C7—C81.508 (4)C25—C261.357 (7)
C7—H7a0.98C25—H250.97
C7—H7b0.98C26—C271.364 (7)
C8—H8a0.98C26—H260.97
C8—H8b0.98C27—C281.380 (5)
C9—C101.536 (3)C27—H270.97
C9—C111.513 (4)C28—H280.97
C9—H90.98C29—C301.38 (2)
C10—H100.98C29—C31i1.46 (2)
C10—H110.98C29—H290.96
C11—C121.383 (4)C30—C311.21 (2)
C11—C161.377 (5)C30—H300.97
C12—C131.383 (5)C31—H310.97
O3···O4ii2.794 (4)O4···C17ii3.347 (4)
O3···C18ii3.203 (5)O4···C18ii3.347 (4)
O3···C19ii3.317 (5)C19···C19iii3.423 (6)
O4···O4ii3.237 (5)
N1—O1—B1106.2 (2)C11—C12—C13120.3 (4)
C1—O2—B1108.6 (2)C11—C12—H12119.9
C3—O3—H3106 (2)C13—C12—H12119.8
C10—O4—H4112 (4)C12—C13—C14120.7 (3)
O1—N1—C1112.3 (2)C12—C13—H13119.6
O1—N1—C2116.7 (2)C14—C13—H13119.6
C1—N1—C2130.9 (3)C13—C14—C15119.5 (4)
O2—C1—N1114.0 (3)C13—C14—H14120.2
O2—C1—C9121.6 (2)C15—C14—H14120.3
N1—C1—C9124.3 (3)C14—C15—C16120.8 (5)
N1—C2—C3113.6 (3)C14—C15—H15119.8
N1—C2—H2a108.4C16—C15—H15119.4
N1—C2—H2b108.6C11—C16—C15120.6 (3)
C3—C2—H2a108.4C11—C16—H16119.7
C3—C2—H2b108.5C15—C16—H16119.7
H2a—C2—H2b109.3C18—C17—C22116.3 (4)
O3—C3—C2108.5 (2)C18—C17—B1122.6 (3)
O3—C3—C4105.5 (2)C22—C17—B1120.9 (3)
O3—C3—C8111.6 (3)C17—C18—C19122.2 (4)
C2—C3—C4108.4 (3)C17—C18—H18119.0
C2—C3—C8112.0 (3)C19—C18—H18118.9
C4—C3—C8110.5 (2)C18—C19—C20120.0 (4)
C3—C4—C5111.5 (3)C18—C19—H19120.2
C3—C4—H4a108.9C20—C19—H19119.8
C3—C4—H4b109.0C19—C20—C21120.1 (5)
C5—C4—H4a108.9C19—C20—H20120.2
C5—C4—H4b109.2C21—C20—H20119.7
H4a—C4—H4b109.3C20—C21—C22120.0 (4)
C4—C5—C6112.2 (3)C20—C21—H21120.1
C4—C5—H5a108.7C22—C21—H21119.9
C4—C5—H5b108.6C17—C22—C21121.5 (4)
C6—C5—H5a109.0C17—C22—H22119.3
C6—C5—H5b109.0C21—C22—H22119.2
H5a—C5—H5b109.3C24—C23—C28116.2 (3)
C5—C6—C7110.2 (3)C24—C23—B1120.2 (3)
C5—C6—H6a109.1C28—C23—B1123.6 (3)
C5—C6—H6b109.1C23—C24—C25121.6 (3)
C7—C6—H6a109.5C23—C24—H24119.2
C7—C6—H6b109.4C25—C24—H24119.2
H6a—C6—H6b109.5C24—C25—C26121.1 (4)
C6—C7—C8111.3 (3)C24—C25—H25119.7
C6—C7—H7a108.9C26—C25—H25119.2
C6—C7—H7b109.2C25—C26—C27118.9 (4)
C8—C7—H7a108.9C25—C26—H26120.8
C8—C7—H7b109.1C27—C26—H26120.3
H7a—C7—H7b109.3C26—C27—C28120.2 (4)
C3—C8—C7113.3 (3)C26—C27—H27119.9
C3—C8—H8a108.4C28—C27—H27119.9
C3—C8—H8b108.5C23—C28—C27122.0 (4)
C7—C8—H8a108.6C23—C28—H28118.9
C7—C8—H8b108.6C27—C28—H28119.0
H8a—C8—H8b109.4C30—C29—C31i115 (1)
C1—C9—C10110.4 (3)C30—C29—H29122.4
C1—C9—C11111.2 (2)C31i—C29—H29122.5
C1—C9—H9108.3C29—C30—C31117 (1)
C10—C9—C11110.5 (2)C29—C30—H30121.3
C10—C9—H9108.2C31—C30—H30121.5
C11—C9—H9108.1C29i—C31—C30119 (1)
O4—C10—C9112.0 (2)C29i—C31—H31120.6
O4—C10—H10108.9C30—C31—H31120.2
O4—C10—H11108.9O1—B1—O298.2 (2)
C9—C10—H10108.9O1—B1—C17112.7 (2)
C9—C10—H11108.8O1—B1—C23110.2 (3)
H10—C10—H11109.4O2—B1—C17108.3 (3)
C9—C11—C12122.3 (3)O2—B1—C23110.1 (3)
C9—C11—C16119.8 (3)C17—B1—C23115.8 (3)
C12—C11—C16118.0 (3)
O1—N1—C1—O21.5 (3)C3—C4—C5—C655.6 (4)
O1—N1—C1—C9175.7 (2)C3—C8—C7—C654.9 (4)
O1—N1—C2—C383.9 (3)C4—C3—C8—C752.6 (3)
O1—B1—O2—C16.4 (3)C4—C5—C6—C756.7 (4)
O1—B1—C17—C18136.2 (3)C5—C4—C3—C852.2 (3)
O1—B1—C17—C2248.0 (4)C5—C6—C7—C855.7 (4)
O1—B1—C23—C2443.2 (4)C9—C1—O2—B1179.1 (2)
O1—B1—C23—C28136.5 (3)C9—C11—C12—C13178.8 (3)
O2—C1—N1—C2176.6 (3)C9—C11—C16—C15178.9 (3)
O2—C1—C9—C1036.1 (3)C10—C9—C11—C1289.3 (4)
O2—C1—C9—C1186.9 (3)C10—C9—C11—C1689.9 (3)
O2—B1—O1—N16.9 (3)C11—C12—C13—C140.4 (6)
O2—B1—C17—C1828.6 (4)C11—C16—C15—C140.5 (6)
O2—B1—C17—C22155.6 (3)C12—C11—C16—C150.3 (5)
O2—B1—C23—C2464.1 (4)C12—C13—C14—C151.2 (7)
O2—B1—C23—C28116.2 (4)C13—C12—C11—C160.3 (5)
O3—C3—C2—N155.3 (4)C13—C14—C15—C161.2 (7)
O3—C3—C4—C568.6 (3)C17—C18—C19—C200.4 (5)
O3—C3—C8—C764.4 (3)C17—C22—C21—C200.2 (6)
O4—C10—C9—C160.5 (3)C17—B1—C23—C24172.6 (3)
O4—C10—C9—C11176.1 (3)C17—B1—C23—C287.1 (5)
N1—O1—B1—C17106.9 (3)C18—C17—C22—C210.7 (5)
N1—O1—B1—C23122.0 (3)C18—C17—B1—C2395.7 (4)
N1—C1—O2—B13.6 (3)C18—C19—C20—C210.9 (5)
N1—C1—C9—C10146.8 (2)C19—C18—C17—C220.4 (5)
N1—C1—C9—C1190.1 (3)C19—C18—C17—B1175.5 (3)
N1—C2—C3—C4169.4 (2)C19—C20—C21—C220.7 (6)
N1—C2—C3—C868.4 (3)C21—C22—C17—B1175.4 (3)
C1—O2—B1—C17110.9 (3)C22—C17—B1—C2380.1 (4)
C1—O2—B1—C23121.5 (3)C23—C24—C25—C260.5 (6)
C1—N1—O1—B15.9 (3)C23—C28—C27—C260.5 (7)
C1—N1—C2—C3101.2 (4)C24—C23—C28—C272.1 (6)
C1—C9—C11—C1233.7 (4)C24—C25—C26—C271.1 (7)
C1—C9—C11—C16147.1 (3)C25—C24—C23—C282.1 (5)
C2—N1—O1—B1178.3 (2)C25—C24—C23—B1178.2 (4)
C2—N1—C1—C90.7 (4)C25—C26—C27—C281.1 (7)
C2—C3—C4—C5175.3 (3)C27—C28—C23—B1178.2 (4)
C2—C3—C8—C7173.6 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x, y, z; (iii) x, y, z+1.
 

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