4-[(1-Hydroxycyclohexyl)methyl]-5-(2-hydroxy-1-phenylethyl)-2,2-diphenyl-1,3-dioxa-4-azonia-2-borata-4-cyclopentene benzene hemisolvate, C
28H
32BNO
4·0.5C
6H
6, 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
CCDC reference: 200757
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
Alert Level B:
PLAT_420 Alert B D-H Without Acceptor O(4) - H(4) ?
| Author response: See Comment, final paragraph
|
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
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).
Crystal data top
C28H32BNO4·0.5C6H6 | F(000) = 1060 |
Mr = 496.42 | Dx = 1.164 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.310 (1) Å | Cell parameters from 25 reflections |
b = 22.089 (2) Å | θ = 15.1–18.9° |
c = 10.965 (1) Å | µ = 0.08 mm−1 |
β = 108.26 (1)° | T = 294 K |
V = 2831.4 (5) Å3 | Prism, colorless |
Z = 4 | 0.45 × 0.25 × 0.25 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 2467 reflections with I > 3σ(I) |
Radiation source: X-ray tube | Rint = 0.0 |
Graphite monochromator | θmax = 27.5°, θmin = 0.0° |
ω–2θ scans | h = 0→15 |
Absorption correction: ψ scan (local program; Rettig, 1978) | k = 0→28 |
Tmin = 0.96, Tmax = 0.98 | l = −14→13 |
6443 measured reflections | 3 standard reflections every 150 reflections |
6443 independent reflections | intensity decay: 0.0% |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.054 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.0004Fo2] |
S = 1.96 | (Δ/σ)max = 0.04 |
6443 reflections | Δρmax = 0.35 e Å−3 |
342 parameters | Δρmin = −0.36 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.0772 (2) | 0.1700 (1) | 0.1423 (2) | 0.061 (1) | |
O2 | 0.1889 (2) | 0.0819 (1) | 0.1973 (2) | 0.052 (1) | |
O3 | −0.0550 (2) | 0.1004 (1) | −0.1830 (2) | 0.064 (1) | |
O4 | 0.1218 (2) | −0.0300 (1) | 0.0071 (3) | 0.075 (1) | |
N1 | 0.1099 (2) | 0.1450 (1) | 0.0435 (2) | 0.049 (1) | |
C1 | 0.1725 (2) | 0.0970 (1) | 0.0794 (3) | 0.045 (3) | |
C2 | 0.0769 (3) | 0.1779 (1) | −0.0776 (3) | 0.052 (3) | |
C3 | −0.0443 (3) | 0.1641 (1) | −0.1630 (3) | 0.049 (3) | |
C4 | −0.0605 (3) | 0.1915 (1) | −0.2954 (3) | 0.067 (3) | |
C5 | −0.1829 (4) | 0.1841 (2) | −0.3831 (3) | 0.094 (4) | |
C6 | −0.2688 (4) | 0.2104 (2) | −0.3251 (5) | 0.107 (5) | |
C7 | −0.2548 (3) | 0.1817 (2) | −0.1956 (4) | 0.091 (4) | |
C8 | −0.1340 (3) | 0.1885 (1) | −0.1067 (3) | 0.064 (3) | |
C9 | 0.2269 (2) | 0.0627 (1) | −0.0043 (3) | 0.045 (3) | |
C10 | 0.2319 (3) | −0.0052 (1) | 0.0274 (3) | 0.058 (3) | |
C11 | 0.3453 (3) | 0.0867 (1) | 0.0096 (3) | 0.053 (3) | |
C12 | 0.4165 (3) | 0.1093 (2) | 0.1245 (3) | 0.073 (3) | |
C13 | 0.5249 (3) | 0.1298 (2) | 0.1335 (4) | 0.092 (4) | |
C14 | 0.5634 (3) | 0.1278 (2) | 0.0304 (5) | 0.092 (4) | |
C15 | 0.4942 (4) | 0.1065 (2) | −0.0829 (4) | 0.094 (4) | |
C16 | 0.3856 (3) | 0.0857 (2) | −0.0942 (3) | 0.077 (3) | |
C17 | 0.0165 (3) | 0.0886 (1) | 0.2813 (3) | 0.053 (3) | |
C18 | 0.0235 (3) | 0.0271 (2) | 0.3070 (3) | 0.062 (3) | |
C19 | −0.0625 (4) | −0.0041 (2) | 0.3371 (3) | 0.079 (4) | |
C20 | −0.1568 (4) | 0.0256 (2) | 0.3428 (4) | 0.087 (4) | |
C21 | −0.1683 (3) | 0.0863 (3) | 0.3171 (4) | 0.095 (4) | |
C22 | −0.0823 (3) | 0.1176 (2) | 0.2864 (4) | 0.082 (4) | |
C23 | 0.2022 (3) | 0.1600 (1) | 0.3779 (3) | 0.055 (3) | |
C24 | 0.2851 (3) | 0.1990 (2) | 0.3635 (3) | 0.075 (3) | |
C25 | 0.3604 (3) | 0.2277 (2) | 0.4671 (4) | 0.089 (4) | |
C26 | 0.3554 (4) | 0.2191 (2) | 0.5878 (4) | 0.090 (4) | |
C27 | 0.2728 (4) | 0.1821 (2) | 0.6052 (3) | 0.088 (4) | |
C28 | 0.1971 (3) | 0.1532 (2) | 0.5015 (3) | 0.071 (3) | |
C29 | 0.4421 (9) | 0.4792 (5) | 0.0751 (11) | 0.28 (2) | |
C30 | 0.5262 (11) | 0.4437 (4) | 0.0519 (12) | 0.27 (2) | |
C31 | 0.5949 (9) | 0.4690 (7) | 0.0111 (12) | 0.33 (2) | |
B1 | 0.1188 (3) | 0.1260 (2) | 0.2563 (3) | 0.051 (3) | |
H2a | 0.0824 | 0.2214 | −0.0587 | 0.065* | |
H2b | 0.1301 | 0.1674 | −0.1244 | 0.065* | |
H3 | −0.069 (3) | 0.0864 (16) | −0.119 (3) | 0.083 (13)* | |
H4 | 0.083 (4) | −0.032 (2) | −0.074 (5) | 0.14 (2)* | |
H4a | −0.0420 | 0.2348 | −0.2855 | 0.080* | |
H4b | −0.0086 | 0.1714 | −0.3343 | 0.080* | |
H5a | −0.1906 | 0.2046 | −0.4646 | 0.107* | |
H5b | −0.1986 | 0.1408 | −0.3991 | 0.107* | |
H6a | −0.2566 | 0.2541 | −0.3145 | 0.120* | |
H6b | −0.3461 | 0.2025 | −0.3827 | 0.120* | |
H7a | −0.3072 | 0.2015 | −0.1566 | 0.104* | |
H7b | −0.2736 | 0.1386 | −0.2075 | 0.104* | |
H8a | −0.1188 | 0.2316 | −0.0876 | 0.077* | |
H8b | −0.1272 | 0.1666 | −0.0270 | 0.077* | |
H9 | 0.1795 | 0.0680 | −0.0940 | 0.058* | |
H10 | 0.2689 | −0.0265 | −0.0273 | 0.071* | |
H11 | 0.2772 | −0.0108 | 0.1177 | 0.071* | |
H12 | 0.3903 | 0.1109 | 0.1991 | 0.086* | |
H13 | 0.5739 | 0.1456 | 0.2143 | 0.105* | |
H14 | 0.6400 | 0.1415 | 0.0380 | 0.104* | |
H15 | 0.5211 | 0.1054 | −0.1571 | 0.107* | |
H16 | 0.3372 | 0.0703 | −0.1761 | 0.090* | |
H18 | 0.0908 | 0.0051 | 0.3041 | 0.074* | |
H19 | −0.0553 | −0.0471 | 0.3539 | 0.092* | |
H20 | −0.2166 | 0.0040 | 0.3648 | 0.100* | |
H21 | −0.2363 | 0.1076 | 0.3204 | 0.108* | |
H22 | −0.0916 | 0.1605 | 0.2678 | 0.095* | |
H24 | 0.2901 | 0.2064 | 0.2784 | 0.088* | |
H25 | 0.4182 | 0.2543 | 0.4542 | 0.102* | |
H26 | 0.4093 | 0.2389 | 0.6606 | 0.102* | |
H27 | 0.2670 | 0.1762 | 0.6906 | 0.101* | |
H28 | 0.1386 | 0.1273 | 0.5156 | 0.084* | |
H29 | 0.4100 | 0.4703 | 0.1428 | 0.29* | |
H30 | 0.5297 | 0.4006 | 0.0675 | 0.28* | |
H31 | 0.6733 | 0.4551 | 0.0356 | 0.34* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.085 (2) | 0.049 (1) | 0.059 (1) | 0.020 (1) | 0.035 (1) | 0.002 (1) |
O2 | 0.064 (1) | 0.046 (1) | 0.051 (1) | 0.011 (1) | 0.025 (1) | 0.005 (1) |
O3 | 0.092 (2) | 0.037 (1) | 0.071 (2) | −0.006 (1) | 0.037 (1) | 0.001 (1) |
O4 | 0.090 (2) | 0.066 (2) | 0.070 (2) | −0.028 (1) | 0.027 (1) | 0.001 (1) |
N1 | 0.056 (2) | 0.046 (2) | 0.053 (1) | 0.005 (1) | 0.026 (1) | 0.003 (1) |
C1 | 0.045 (2) | 0.040 (2) | 0.055 (2) | −0.002 (1) | 0.020 (1) | 0.003 (2) |
C2 | 0.063 (2) | 0.040 (2) | 0.060 (2) | 0.002 (2) | 0.029 (2) | 0.011 (1) |
C3 | 0.059 (2) | 0.035 (2) | 0.054 (2) | −0.001 (1) | 0.021 (2) | 0.004 (1) |
C4 | 0.079 (3) | 0.062 (2) | 0.063 (2) | −0.007 (2) | 0.025 (2) | 0.015 (2) |
C5 | 0.097 (3) | 0.099 (3) | 0.070 (2) | −0.027 (3) | 0.001 (2) | 0.031 (2) |
C6 | 0.069 (3) | 0.105 (4) | 0.128 (4) | −0.002 (2) | 0.004 (3) | 0.035 (3) |
C7 | 0.061 (3) | 0.098 (3) | 0.116 (3) | 0.002 (2) | 0.029 (2) | 0.013 (3) |
C8 | 0.061 (2) | 0.056 (2) | 0.080 (2) | 0.004 (2) | 0.031 (2) | 0.002 (2) |
C9 | 0.046 (2) | 0.043 (2) | 0.049 (2) | 0.004 (1) | 0.019 (1) | 0.000 (1) |
C10 | 0.071 (2) | 0.047 (2) | 0.061 (2) | 0.004 (2) | 0.028 (2) | −0.004 (2) |
C11 | 0.048 (2) | 0.048 (2) | 0.067 (2) | 0.007 (2) | 0.026 (2) | 0.005 (2) |
C12 | 0.054 (2) | 0.099 (3) | 0.069 (2) | −0.002 (2) | 0.021 (2) | −0.008 (2) |
C13 | 0.056 (2) | 0.118 (4) | 0.098 (3) | −0.005 (2) | 0.017 (2) | −0.019 (3) |
C14 | 0.059 (2) | 0.092 (3) | 0.133 (4) | −0.006 (2) | 0.044 (3) | −0.005 (3) |
C15 | 0.079 (3) | 0.122 (4) | 0.102 (3) | −0.018 (3) | 0.058 (3) | −0.013 (3) |
C16 | 0.066 (2) | 0.094 (3) | 0.082 (2) | −0.013 (2) | 0.038 (2) | −0.014 (2) |
C17 | 0.059 (2) | 0.057 (2) | 0.046 (2) | 0.003 (2) | 0.019 (2) | −0.006 (2) |
C18 | 0.073 (2) | 0.055 (2) | 0.065 (2) | −0.005 (2) | 0.032 (2) | −0.005 (2) |
C19 | 0.094 (3) | 0.071 (3) | 0.081 (3) | −0.023 (2) | 0.042 (2) | −0.010 (2) |
C20 | 0.078 (3) | 0.110 (4) | 0.079 (3) | −0.033 (3) | 0.033 (2) | −0.017 (3) |
C21 | 0.057 (3) | 0.129 (4) | 0.107 (3) | 0.011 (3) | 0.037 (2) | −0.009 (3) |
C22 | 0.069 (3) | 0.079 (3) | 0.108 (3) | 0.016 (2) | 0.040 (2) | 0.006 (2) |
C23 | 0.064 (2) | 0.044 (2) | 0.061 (2) | 0.003 (2) | 0.027 (2) | −0.003 (2) |
C24 | 0.091 (3) | 0.071 (2) | 0.073 (2) | −0.018 (2) | 0.040 (2) | −0.009 (2) |
C25 | 0.087 (3) | 0.080 (3) | 0.109 (3) | −0.027 (2) | 0.043 (3) | −0.022 (3) |
C26 | 0.092 (3) | 0.087 (3) | 0.084 (3) | −0.006 (3) | 0.019 (2) | −0.027 (2) |
C27 | 0.118 (3) | 0.089 (3) | 0.059 (2) | −0.018 (3) | 0.030 (2) | −0.011 (2) |
C28 | 0.091 (3) | 0.067 (2) | 0.060 (2) | −0.016 (2) | 0.031 (2) | −0.004 (2) |
C29 | 0.279 (10) | 0.268 (11) | 0.399 (14) | 0.124 (9) | 0.257 (11) | 0.196 (11) |
C30 | 0.297 (12) | 0.173 (7) | 0.468 (17) | 0.094 (8) | 0.283 (12) | 0.134 (9) |
C31 | 0.226 (10) | 0.407 (17) | 0.443 (16) | 0.192 (11) | 0.236 (11) | 0.283 (14) |
B1 | 0.064 (2) | 0.042 (2) | 0.054 (2) | 0.011 (2) | 0.027 (2) | 0.002 (2) |
Geometric parameters (Å, º) top
O1—N1 | 1.383 (4) | C12—H12 | 0.97 |
O1—B1 | 1.539 (4) | C13—C14 | 1.357 (7) |
O2—C1 | 1.288 (4) | C13—H13 | 0.97 |
O2—B1 | 1.569 (5) | C14—C15 | 1.352 (6) |
O3—C3 | 1.424 (3) | C14—H14 | 0.97 |
O3—H3 | 0.83 (4) | C15—C16 | 1.382 (6) |
O4—C10 | 1.413 (4) | C15—H15 | 0.97 |
O4—H4 | 0.87 (4) | C16—H16 | 0.97 |
N1—C1 | 1.297 (3) | C17—C18 | 1.385 (5) |
N1—C2 | 1.456 (4) | C17—C22 | 1.391 (5) |
C1—C9 | 1.500 (4) | C17—B1 | 1.600 (5) |
C2—C3 | 1.523 (4) | C18—C19 | 1.387 (6) |
C2—H2a | 0.98 | C18—H18 | 0.97 |
C2—H2b | 0.98 | C19—C20 | 1.352 (7) |
C3—C4 | 1.527 (4) | C19—H19 | 0.97 |
C3—C8 | 1.523 (5) | C20—C21 | 1.368 (8) |
C4—C5 | 1.521 (5) | C20—H20 | 0.97 |
C4—H4a | 0.98 | C21—C22 | 1.391 (7) |
C4—H4b | 0.98 | C21—H21 | 0.97 |
C5—C6 | 1.510 (7) | C22—H22 | 0.97 |
C5—H5a | 0.98 | C23—C24 | 1.382 (5) |
C5—H5b | 0.98 | C23—C28 | 1.384 (5) |
C6—C7 | 1.515 (7) | C23—B1 | 1.593 (4) |
C6—H6a | 0.98 | C24—C25 | 1.375 (5) |
C6—H6b | 0.98 | C24—H24 | 0.97 |
C7—C8 | 1.508 (4) | C25—C26 | 1.357 (7) |
C7—H7a | 0.98 | C25—H25 | 0.97 |
C7—H7b | 0.98 | C26—C27 | 1.364 (7) |
C8—H8a | 0.98 | C26—H26 | 0.97 |
C8—H8b | 0.98 | C27—C28 | 1.380 (5) |
C9—C10 | 1.536 (3) | C27—H27 | 0.97 |
C9—C11 | 1.513 (4) | C28—H28 | 0.97 |
C9—H9 | 0.98 | C29—C30 | 1.38 (2) |
C10—H10 | 0.98 | C29—C31i | 1.46 (2) |
C10—H11 | 0.98 | C29—H29 | 0.96 |
C11—C12 | 1.383 (4) | C30—C31 | 1.21 (2) |
C11—C16 | 1.377 (5) | C30—H30 | 0.97 |
C12—C13 | 1.383 (5) | C31—H31 | 0.97 |
| | | |
O3···O4ii | 2.794 (4) | O4···C17ii | 3.347 (4) |
O3···C18ii | 3.203 (5) | O4···C18ii | 3.347 (4) |
O3···C19ii | 3.317 (5) | C19···C19iii | 3.423 (6) |
O4···O4ii | 3.237 (5) | | |
| | | |
N1—O1—B1 | 106.2 (2) | C11—C12—C13 | 120.3 (4) |
C1—O2—B1 | 108.6 (2) | C11—C12—H12 | 119.9 |
C3—O3—H3 | 106 (2) | C13—C12—H12 | 119.8 |
C10—O4—H4 | 112 (4) | C12—C13—C14 | 120.7 (3) |
O1—N1—C1 | 112.3 (2) | C12—C13—H13 | 119.6 |
O1—N1—C2 | 116.7 (2) | C14—C13—H13 | 119.6 |
C1—N1—C2 | 130.9 (3) | C13—C14—C15 | 119.5 (4) |
O2—C1—N1 | 114.0 (3) | C13—C14—H14 | 120.2 |
O2—C1—C9 | 121.6 (2) | C15—C14—H14 | 120.3 |
N1—C1—C9 | 124.3 (3) | C14—C15—C16 | 120.8 (5) |
N1—C2—C3 | 113.6 (3) | C14—C15—H15 | 119.8 |
N1—C2—H2a | 108.4 | C16—C15—H15 | 119.4 |
N1—C2—H2b | 108.6 | C11—C16—C15 | 120.6 (3) |
C3—C2—H2a | 108.4 | C11—C16—H16 | 119.7 |
C3—C2—H2b | 108.5 | C15—C16—H16 | 119.7 |
H2a—C2—H2b | 109.3 | C18—C17—C22 | 116.3 (4) |
O3—C3—C2 | 108.5 (2) | C18—C17—B1 | 122.6 (3) |
O3—C3—C4 | 105.5 (2) | C22—C17—B1 | 120.9 (3) |
O3—C3—C8 | 111.6 (3) | C17—C18—C19 | 122.2 (4) |
C2—C3—C4 | 108.4 (3) | C17—C18—H18 | 119.0 |
C2—C3—C8 | 112.0 (3) | C19—C18—H18 | 118.9 |
C4—C3—C8 | 110.5 (2) | C18—C19—C20 | 120.0 (4) |
C3—C4—C5 | 111.5 (3) | C18—C19—H19 | 120.2 |
C3—C4—H4a | 108.9 | C20—C19—H19 | 119.8 |
C3—C4—H4b | 109.0 | C19—C20—C21 | 120.1 (5) |
C5—C4—H4a | 108.9 | C19—C20—H20 | 120.2 |
C5—C4—H4b | 109.2 | C21—C20—H20 | 119.7 |
H4a—C4—H4b | 109.3 | C20—C21—C22 | 120.0 (4) |
C4—C5—C6 | 112.2 (3) | C20—C21—H21 | 120.1 |
C4—C5—H5a | 108.7 | C22—C21—H21 | 119.9 |
C4—C5—H5b | 108.6 | C17—C22—C21 | 121.5 (4) |
C6—C5—H5a | 109.0 | C17—C22—H22 | 119.3 |
C6—C5—H5b | 109.0 | C21—C22—H22 | 119.2 |
H5a—C5—H5b | 109.3 | C24—C23—C28 | 116.2 (3) |
C5—C6—C7 | 110.2 (3) | C24—C23—B1 | 120.2 (3) |
C5—C6—H6a | 109.1 | C28—C23—B1 | 123.6 (3) |
C5—C6—H6b | 109.1 | C23—C24—C25 | 121.6 (3) |
C7—C6—H6a | 109.5 | C23—C24—H24 | 119.2 |
C7—C6—H6b | 109.4 | C25—C24—H24 | 119.2 |
H6a—C6—H6b | 109.5 | C24—C25—C26 | 121.1 (4) |
C6—C7—C8 | 111.3 (3) | C24—C25—H25 | 119.7 |
C6—C7—H7a | 108.9 | C26—C25—H25 | 119.2 |
C6—C7—H7b | 109.2 | C25—C26—C27 | 118.9 (4) |
C8—C7—H7a | 108.9 | C25—C26—H26 | 120.8 |
C8—C7—H7b | 109.1 | C27—C26—H26 | 120.3 |
H7a—C7—H7b | 109.3 | C26—C27—C28 | 120.2 (4) |
C3—C8—C7 | 113.3 (3) | C26—C27—H27 | 119.9 |
C3—C8—H8a | 108.4 | C28—C27—H27 | 119.9 |
C3—C8—H8b | 108.5 | C23—C28—C27 | 122.0 (4) |
C7—C8—H8a | 108.6 | C23—C28—H28 | 118.9 |
C7—C8—H8b | 108.6 | C27—C28—H28 | 119.0 |
H8a—C8—H8b | 109.4 | C30—C29—C31i | 115 (1) |
C1—C9—C10 | 110.4 (3) | C30—C29—H29 | 122.4 |
C1—C9—C11 | 111.2 (2) | C31i—C29—H29 | 122.5 |
C1—C9—H9 | 108.3 | C29—C30—C31 | 117 (1) |
C10—C9—C11 | 110.5 (2) | C29—C30—H30 | 121.3 |
C10—C9—H9 | 108.2 | C31—C30—H30 | 121.5 |
C11—C9—H9 | 108.1 | C29i—C31—C30 | 119 (1) |
O4—C10—C9 | 112.0 (2) | C29i—C31—H31 | 120.6 |
O4—C10—H10 | 108.9 | C30—C31—H31 | 120.2 |
O4—C10—H11 | 108.9 | O1—B1—O2 | 98.2 (2) |
C9—C10—H10 | 108.9 | O1—B1—C17 | 112.7 (2) |
C9—C10—H11 | 108.8 | O1—B1—C23 | 110.2 (3) |
H10—C10—H11 | 109.4 | O2—B1—C17 | 108.3 (3) |
C9—C11—C12 | 122.3 (3) | O2—B1—C23 | 110.1 (3) |
C9—C11—C16 | 119.8 (3) | C17—B1—C23 | 115.8 (3) |
C12—C11—C16 | 118.0 (3) | | |
| | | |
O1—N1—C1—O2 | 1.5 (3) | C3—C4—C5—C6 | 55.6 (4) |
O1—N1—C1—C9 | −175.7 (2) | C3—C8—C7—C6 | −54.9 (4) |
O1—N1—C2—C3 | −83.9 (3) | C4—C3—C8—C7 | 52.6 (3) |
O1—B1—O2—C1 | −6.4 (3) | C4—C5—C6—C7 | −56.7 (4) |
O1—B1—C17—C18 | 136.2 (3) | C5—C4—C3—C8 | −52.2 (3) |
O1—B1—C17—C22 | −48.0 (4) | C5—C6—C7—C8 | 55.7 (4) |
O1—B1—C23—C24 | −43.2 (4) | C9—C1—O2—B1 | −179.1 (2) |
O1—B1—C23—C28 | 136.5 (3) | C9—C11—C12—C13 | 178.8 (3) |
O2—C1—N1—C2 | 176.6 (3) | C9—C11—C16—C15 | −178.9 (3) |
O2—C1—C9—C10 | 36.1 (3) | C10—C9—C11—C12 | −89.3 (4) |
O2—C1—C9—C11 | −86.9 (3) | C10—C9—C11—C16 | 89.9 (3) |
O2—B1—O1—N1 | 6.9 (3) | C11—C12—C13—C14 | −0.4 (6) |
O2—B1—C17—C18 | 28.6 (4) | C11—C16—C15—C14 | 0.5 (6) |
O2—B1—C17—C22 | −155.6 (3) | C12—C11—C16—C15 | 0.3 (5) |
O2—B1—C23—C24 | 64.1 (4) | C12—C13—C14—C15 | 1.2 (7) |
O2—B1—C23—C28 | −116.2 (4) | C13—C12—C11—C16 | −0.3 (5) |
O3—C3—C2—N1 | −55.3 (4) | C13—C14—C15—C16 | −1.2 (7) |
O3—C3—C4—C5 | 68.6 (3) | C17—C18—C19—C20 | −0.4 (5) |
O3—C3—C8—C7 | −64.4 (3) | C17—C22—C21—C20 | −0.2 (6) |
O4—C10—C9—C1 | 60.5 (3) | C17—B1—C23—C24 | −172.6 (3) |
O4—C10—C9—C11 | −176.1 (3) | C17—B1—C23—C28 | 7.1 (5) |
N1—O1—B1—C17 | −106.9 (3) | C18—C17—C22—C21 | 0.7 (5) |
N1—O1—B1—C23 | 122.0 (3) | C18—C17—B1—C23 | −95.7 (4) |
N1—C1—O2—B1 | 3.6 (3) | C18—C19—C20—C21 | 0.9 (5) |
N1—C1—C9—C10 | −146.8 (2) | C19—C18—C17—C22 | −0.4 (5) |
N1—C1—C9—C11 | 90.1 (3) | C19—C18—C17—B1 | 175.5 (3) |
N1—C2—C3—C4 | −169.4 (2) | C19—C20—C21—C22 | −0.7 (6) |
N1—C2—C3—C8 | 68.4 (3) | C21—C22—C17—B1 | −175.4 (3) |
C1—O2—B1—C17 | 110.9 (3) | C22—C17—B1—C23 | 80.1 (4) |
C1—O2—B1—C23 | −121.5 (3) | C23—C24—C25—C26 | −0.5 (6) |
C1—N1—O1—B1 | −5.9 (3) | C23—C28—C27—C26 | 0.5 (7) |
C1—N1—C2—C3 | 101.2 (4) | C24—C23—C28—C27 | −2.1 (6) |
C1—C9—C11—C12 | 33.7 (4) | C24—C25—C26—C27 | −1.1 (7) |
C1—C9—C11—C16 | −147.1 (3) | C25—C24—C23—C28 | 2.1 (5) |
C2—N1—O1—B1 | 178.3 (2) | C25—C24—C23—B1 | −178.2 (4) |
C2—N1—C1—C9 | −0.7 (4) | C25—C26—C27—C28 | 1.1 (7) |
C2—C3—C4—C5 | −175.3 (3) | C27—C28—C23—B1 | 178.2 (4) |
C2—C3—C8—C7 | 173.6 (3) | | |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z; (iii) −x, −y, −z+1. |