organic compounds
N,N-Diethylhydroxylamine(O–B)triphenylboroxin N,N-dimethylformamide [2-(diethylammoniooxy)-2,4,6-triphenyl-1,3,5-trioxa-4,6-dibora-2-boratacyclohexane N,N-dimethylformamide], C22H26B3NO4·C3H7NO, contains one molecule of N,N-diethylhydroxylamine in its N-oxide form added to a boroxin heterocycle, with N,N-dimethylformamide solvent linked by an OH—N hydrogen bond to the protonated hydroxylamine moiety.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011820/om6095sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011820/om6095IVsup2.hkl |
CCDC reference: 193738
Computing details top
Data collection: D*TREK (Molecular Structure Corporation, 1997); cell refinement: D*TREK; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.
(IV) top
Crystal data top
C22H26B3NO4·C3H7NO | Z = 2 |
Mr = 473.98 | F(000) = 504 |
Triclinic, P1 | Dx = 1.151 Mg m−3 |
a = 13.0046 (7) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 14.071 (1) Å | Cell parameters from 5239 reflections |
c = 7.9235 (8) Å | θ = 3.0–25.0° |
α = 92.79 (2)° | µ = 0.08 mm−1 |
β = 96.95 (2)° | T = 273 K |
γ = 71.85 (1)° | Prism, colorless |
V = 1367.5 (2) Å3 | 0.50 × 0.25 × 0.10 mm |
Data collection top
Quantum CCD diffractometer | 4675 independent reflections |
Radiation source: X-ray tube | 2346 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.041 |
CCD scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: multi-scan (d*TREK; Molecular Structure Corporation, 1997) | h = −15→15 |
Tmin = 0.96, Tmax = 0.99 | k = −16→16 |
11054 measured reflections | l = −9→9 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.264 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2) + 0.0025(Fo2)2] |
S = 1.40 | (Δ/σ)max = 0.05 |
4675 reflections | Δρmax = 0.56 e Å−3 |
320 parameters | Δρmin = −0.38 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.3832 (2) | 0.3713 (1) | 0.4080 (2) | 0.0628 (6) | |
O2 | 0.2525 (2) | 0.3109 (1) | 0.2394 (2) | 0.0594 (6) | |
O3 | 0.3847 (1) | 0.2002 (1) | 0.4311 (2) | 0.0611 (6) | |
O4 | 0.4895 (2) | 0.2712 (1) | 0.6457 (2) | 0.0676 (6) | |
O5 | 0.1918 (3) | 0.3016 (4) | 0.6712 (6) | 0.159 (2) | |
N1 | 0.4061 (3) | 0.2907 (2) | 0.7530 (3) | 0.077 (1) | |
N2 | 0.0479 (4) | 0.2484 (6) | 0.5607 (7) | 0.156 (2) | |
C1 | 0.5582 (2) | 0.2322 (2) | 0.3648 (3) | 0.0637 (9) | |
C2 | 0.5975 (3) | 0.1353 (3) | 0.2994 (5) | 0.080 (1) | |
C3 | 0.6889 (4) | 0.1036 (3) | 0.2158 (6) | 0.101 (1) | |
C4 | 0.7470 (4) | 0.1677 (4) | 0.1975 (6) | 0.116 (2) | |
C5 | 0.7118 (4) | 0.2632 (5) | 0.2571 (7) | 0.122 (2) | |
C6 | 0.6177 (3) | 0.2953 (3) | 0.3388 (5) | 0.094 (1) | |
C7 | 0.2345 (2) | 0.4956 (2) | 0.2257 (4) | 0.0592 (8) | |
C8 | 0.2800 (3) | 0.5724 (2) | 0.2653 (4) | 0.070 (1) | |
C9 | 0.2305 (3) | 0.6677 (2) | 0.1980 (5) | 0.089 (1) | |
C10 | 0.1355 (3) | 0.6872 (3) | 0.0952 (6) | 0.098 (1) | |
C11 | 0.0882 (3) | 0.6142 (3) | 0.0561 (6) | 0.107 (1) | |
C12 | 0.1380 (3) | 0.5187 (2) | 0.1185 (5) | 0.083 (1) | |
C13 | 0.2425 (2) | 0.1349 (2) | 0.2660 (3) | 0.0538 (8) | |
C14 | 0.1576 (3) | 0.1468 (2) | 0.1367 (4) | 0.075 (1) | |
C15 | 0.1112 (3) | 0.0713 (3) | 0.0964 (6) | 0.099 (1) | |
C16 | 0.1477 (3) | −0.0165 (3) | 0.1836 (6) | 0.096 (1) | |
C17 | 0.2316 (3) | −0.0308 (2) | 0.3096 (5) | 0.094 (1) | |
C18 | 0.2788 (3) | 0.0435 (2) | 0.3493 (4) | 0.075 (1) | |
C19 | 0.4386 (4) | 0.2206 (4) | 0.8928 (5) | 0.119 (2) | |
C20 | 0.4464 (5) | 0.1221 (4) | 0.8347 (7) | 0.146 (2) | |
C21 | 0.3676 (7) | 0.4062 (7) | 0.8125 (9) | 0.186 (3) | |
C22 | 0.440 (1) | 0.4309 (7) | 0.901 (2) | 0.252 (6) | |
C23 | 0.1440 (6) | 0.2393 (7) | 0.6496 (9) | 0.179 (3) | |
C24 | 0.0018 (8) | 0.167 (1) | 0.536 (1) | 0.269 (6) | |
C25 | −0.0020 (8) | 0.3382 (9) | 0.485 (1) | 0.219 (4) | |
B1 | 0.4506 (3) | 0.2692 (3) | 0.4587 (4) | 0.0580 (9) | |
B2 | 0.2930 (3) | 0.3881 (2) | 0.2964 (4) | 0.0531 (9) | |
B3 | 0.2965 (2) | 0.2179 (2) | 0.3158 (4) | 0.0518 (9) | |
H2 | 0.5580 | 0.0879 | 0.3136 | 0.097* | |
H3 | 0.7127 | 0.0356 | 0.1696 | 0.121* | |
H4 | 0.8137 | 0.1453 | 0.1415 | 0.139* | |
H5 | 0.7527 | 0.3096 | 0.2430 | 0.147* | |
H6 | 0.5930 | 0.3648 | 0.3796 | 0.113* | |
H8 | 0.3478 | 0.5593 | 0.3418 | 0.085* | |
H9 | 0.2646 | 0.7205 | 0.2250 | 0.106* | |
H10 | 0.1004 | 0.7543 | 0.0488 | 0.118* | |
H11 | 0.0186 | 0.6292 | −0.0163 | 0.129* | |
H12 | 0.1041 | 0.4663 | 0.0864 | 0.100* | |
H14 | 0.1303 | 0.2094 | 0.0732 | 0.090* | |
H15 | 0.0516 | 0.0811 | 0.0039 | 0.119* | |
H16 | 0.1131 | −0.0688 | 0.1554 | 0.116* | |
H17 | 0.2586 | −0.0939 | 0.3714 | 0.113* | |
H18 | 0.3399 | 0.0319 | 0.4391 | 0.090* | |
H19B | 0.3845 | 0.2411 | 0.9743 | 0.143* | |
H19A | 0.5097 | 0.2214 | 0.9493 | 0.143* | |
H20C | 0.5102 | 0.0958 | 0.7725 | 0.176* | |
H20A | 0.3805 | 0.1229 | 0.7592 | 0.176* | |
H20B | 0.4535 | 0.0793 | 0.9322 | 0.176* | |
H21B | 0.3039 | 0.4187 | 0.8759 | 0.222* | |
H21A | 0.3446 | 0.4490 | 0.7096 | 0.222* | |
H22A | 0.4621 | 0.3905 | 1.0060 | 0.310* | |
H22B | 0.4154 | 0.5019 | 0.9338 | 0.310* | |
H22C | 0.5046 | 0.4183 | 0.8394 | 0.310* | |
H23 | 0.1800 | 0.1744 | 0.7040 | 0.216* | |
H24 | −0.0682 | 0.1898 | 0.4646 | 0.332* | |
H25 | 0.0519 | 0.1117 | 0.4781 | 0.332* | |
H26 | −0.0085 | 0.1458 | 0.6455 | 0.332* | |
H27 | −0.0132 | 0.3923 | 0.5717 | 0.262* | |
H28 | 0.0429 | 0.3507 | 0.4028 | 0.262* | |
H29 | −0.0732 | 0.3392 | 0.4260 | 0.262* | |
H30 | 0.345 (3) | 0.283 (2) | 0.696 (4) | 0.071 (9)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.072 (1) | 0.062 (1) | 0.057 (1) | −0.031 (1) | −0.015 (1) | 0.0090 (9) |
O2 | 0.067 (1) | 0.057 (1) | 0.054 (1) | −0.0244 (9) | −0.0144 (9) | 0.0083 (9) |
O3 | 0.067 (1) | 0.065 (1) | 0.055 (1) | −0.029 (1) | −0.0153 (9) | 0.0166 (9) |
O4 | 0.074 (1) | 0.084 (1) | 0.047 (1) | −0.034 (1) | −0.015 (1) | 0.009 (1) |
O5 | 0.100 (3) | 0.213 (4) | 0.168 (4) | −0.062 (3) | 0.012 (3) | −0.047 (3) |
N1 | 0.096 (2) | 0.092 (2) | 0.050 (2) | −0.040 (2) | −0.001 (2) | 0.004 (1) |
N2 | 0.081 (3) | 0.262 (7) | 0.118 (4) | −0.042 (4) | 0.029 (2) | −0.051 (4) |
C1 | 0.063 (2) | 0.082 (2) | 0.047 (2) | −0.030 (2) | −0.014 (1) | 0.013 (1) |
C2 | 0.077 (2) | 0.076 (2) | 0.085 (2) | −0.017 (2) | 0.002 (2) | 0.021 (2) |
C3 | 0.093 (3) | 0.094 (3) | 0.109 (3) | −0.015 (2) | 0.022 (2) | 0.011 (2) |
C4 | 0.084 (3) | 0.149 (4) | 0.116 (4) | −0.032 (3) | 0.028 (3) | −0.007 (3) |
C5 | 0.104 (3) | 0.156 (4) | 0.141 (4) | −0.084 (3) | 0.037 (3) | −0.030 (4) |
C6 | 0.093 (3) | 0.109 (3) | 0.099 (3) | −0.061 (2) | 0.020 (2) | −0.024 (2) |
C7 | 0.064 (2) | 0.057 (2) | 0.058 (2) | −0.020 (1) | 0.005 (1) | 0.005 (1) |
C8 | 0.072 (2) | 0.066 (2) | 0.075 (2) | −0.025 (2) | 0.006 (2) | 0.000 (2) |
C9 | 0.096 (3) | 0.053 (2) | 0.121 (3) | −0.028 (2) | 0.013 (2) | 0.007 (2) |
C10 | 0.092 (3) | 0.059 (2) | 0.136 (4) | −0.015 (2) | −0.002 (3) | 0.025 (2) |
C11 | 0.082 (3) | 0.081 (2) | 0.148 (4) | −0.021 (2) | −0.032 (3) | 0.043 (3) |
C12 | 0.077 (2) | 0.067 (2) | 0.106 (3) | −0.031 (2) | −0.022 (2) | 0.022 (2) |
C13 | 0.054 (2) | 0.055 (2) | 0.051 (1) | −0.018 (1) | −0.002 (1) | −0.002 (1) |
C14 | 0.070 (2) | 0.059 (2) | 0.087 (2) | −0.020 (2) | −0.024 (2) | 0.001 (2) |
C15 | 0.080 (2) | 0.088 (3) | 0.121 (3) | −0.033 (2) | −0.040 (2) | −0.008 (2) |
C16 | 0.100 (3) | 0.067 (2) | 0.124 (3) | −0.041 (2) | −0.020 (3) | −0.008 (2) |
C17 | 0.113 (3) | 0.063 (2) | 0.109 (3) | −0.044 (2) | −0.025 (2) | 0.010 (2) |
C18 | 0.084 (2) | 0.065 (2) | 0.074 (2) | −0.031 (2) | −0.020 (2) | 0.010 (2) |
C19 | 0.158 (4) | 0.143 (4) | 0.063 (2) | −0.060 (3) | −0.006 (2) | 0.029 (3) |
C20 | 0.212 (6) | 0.091 (3) | 0.123 (4) | −0.045 (3) | −0.037 (4) | 0.036 (3) |
C21 | 0.180 (6) | 0.274 (9) | 0.138 (5) | −0.126 (6) | 0.048 (4) | −0.131 (6) |
C22 | 0.31 (1) | 0.189 (7) | 0.29 (1) | −0.074 (8) | 16 (1) | −0.023 (8) |
C23 | 0.111 (5) | 0.29 (1) | 0.117 (5) | −0.031 (5) | 0.019 (4) | −0.043 (5) |
C24 | 0.173 (8) | 0.43 (2) | 0.25 (1) | −0.16 (1) | 0.089 (7) | −0.14 (1) |
C25 | 0.192 (8) | 0.27 (1) | 0.165 (7) | −0.002 (7) | 0.078 (6) | 0.016 (7) |
B1 | 0.063 (2) | 0.068 (2) | 0.045 (2) | −0.028 (2) | −0.012 (1) | 0.012 (1) |
B2 | 0.058 (2) | 0.059 (2) | 0.044 (2) | −0.021 (2) | 0.000 (1) | 0.004 (1) |
B3 | 0.054 (2) | 0.059 (2) | 0.043 (2) | −0.020 (1) | 0.001 (1) | 0.003 (1) |
Geometric parameters (Å, º) top
O1—B1 | 1.477 (4) | C10—H10 | 0.98 |
O1—B2 | 1.346 (4) | C11—C12 | 1.383 (4) |
O2—B2 | 1.384 (4) | C11—H11 | 0.98 |
O2—B3 | 1.390 (3) | C12—H12 | 0.98 |
O3—B1 | 1.475 (4) | C13—C14 | 1.388 (4) |
O3—B3 | 1.343 (3) | C13—C18 | 1.393 (4) |
O4—N1 | 1.411 (4) | C13—B3 | 1.554 (4) |
O4—B1 | 1.508 (3) | C14—C15 | 1.384 (4) |
O5—C23 | 1.22 (1) | C14—H14 | 0.98 |
N1—C19 | 1.454 (4) | C15—C16 | 1.367 (5) |
N1—C21 | 1.610 (8) | C15—H15 | 0.98 |
N1—H30 | 0.90 (3) | C16—C17 | 1.360 (5) |
N2—C23 | 1.330 (8) | C16—H16 | 0.98 |
N2—C24 | 1.44 (1) | C17—C18 | 1.374 (4) |
N2—C25 | 1.36 (1) | C17—H17 | 0.98 |
C1—C2 | 1.396 (5) | C18—H18 | 0.98 |
C1—C6 | 1.383 (4) | C19—C20 | 1.416 (7) |
C1—B1 | 1.595 (5) | C19—H19B | 0.98 |
C2—C3 | 1.371 (5) | C19—H19A | 0.98 |
C2—H2 | 0.98 | C20—H20C | 0.98 |
C3—C4 | 1.368 (6) | C20—H20A | 0.98 |
C3—H3 | 0.98 | C20—H20B | 0.98 |
C4—C5 | 1.358 (7) | C21—C22 | 1.24 (1) |
C4—H4 | 0.98 | C21—H21B | 0.99 |
C5—C6 | 1.393 (6) | C21—H21A | 1.00 |
C5—H5 | 0.98 | C22—H22A | 0.99 |
C6—H6 | 0.98 | C22—H22B | 0.98 |
C7—C8 | 1.392 (4) | C22—H22C | 0.98 |
C7—C12 | 1.385 (4) | C23—H23 | 0.98 |
C7—B2 | 1.563 (4) | C24—H24 | 0.98 |
C8—C9 | 1.396 (4) | C24—H25 | 0.98 |
C8—H8 | 0.98 | C24—H26 | 0.97 |
C9—C10 | 1.354 (5) | C25—H27 | 0.99 |
C9—H9 | 0.98 | C25—H28 | 0.98 |
C10—C11 | 1.359 (5) | C25—H29 | 0.98 |
O3···O5 | 3.257 (5) | N2···C13 | 3.600 (5) |
O5···N1 | 2.741 (5) | C13···C23 | 3.517 (7) |
O5···C21 | 3.157 (8) | C22···C22i | 3.10 (3) |
O5···B3 | 3.283 (6) | C23···B3 | 3.441 (8) |
O5···C19 | 3.353 (6) | ||
B1—O1—B2 | 121.9 (2) | C15—C16—H16 | 119.9 |
B2—O2—B3 | 119.2 (2) | C17—C16—H16 | 120.2 |
B1—O3—B3 | 122.2 (2) | C16—C17—C18 | 119.8 (3) |
N1—O4—B1 | 114.3 (2) | C16—C17—H17 | 120.1 |
O4—N1—C19 | 110.2 (3) | C18—C17—H17 | 120.1 |
O4—N1—C21 | 111.6 (4) | C13—C18—C17 | 122.2 (3) |
O4—N1—H30 | 111 (2) | C13—C18—H18 | 118.8 |
C19—N1—C21 | 113.9 (4) | C17—C18—H18 | 119.0 |
C19—N1—H30 | 107 (2) | N1—C19—C20 | 111.3 (4) |
C21—N1—H30 | 103 (2) | N1—C19—H19B | 109.0 |
C23—N2—C24 | 122.9 (9) | N1—C19—H19A | 109.1 |
C23—N2—C25 | 115.5 (9) | C20—C19—H19B | 109.0 |
C24—N2—C25 | 121.4 (7) | C20—C19—H19A | 109.0 |
C2—C1—C6 | 115.3 (3) | H19B—C19—H19A | 109.4 |
C2—C1—B1 | 122.7 (3) | C19—C20—H20C | 109.5 |
C6—C1—B1 | 121.9 (3) | C19—C20—H20A | 109.5 |
C1—C2—C3 | 123.0 (4) | C19—C20—H20B | 109.5 |
C1—C2—H2 | 118.5 | H20C—C20—H20A | 109.5 |
C3—C2—H2 | 118.5 | H20C—C20—H20B | 109.5 |
C2—C3—C4 | 119.6 (4) | H20A—C20—H20B | 109.4 |
C2—C3—H3 | 120.4 | N1—C21—C22 | 112.8 (9) |
C4—C3—H3 | 119.9 | N1—C21—H21B | 109.3 |
C3—C4—C5 | 119.8 (4) | N1—C21—H21A | 108.8 |
C3—C4—H4 | 120.5 | C22—C21—H21B | 109.6 |
C5—C4—H4 | 119.8 | C22—C21—H21A | 108.6 |
C4—C5—C6 | 120.1 (4) | H21B—C21—H21A | 107.7 |
C4—C5—H5 | 120.0 | C21—C22—H22A | 109.3 |
C6—C5—H5 | 119.9 | C21—C22—H22B | 111.2 |
C1—C6—C5 | 122.1 (4) | C21—C22—H22C | 110.3 |
C1—C6—H6 | 119.0 | H22A—C22—H22B | 108.6 |
C5—C6—H6 | 118.9 | H22A—C22—H22C | 108.3 |
C8—C7—C12 | 116.9 (3) | H22B—C22—H22C | 109.1 |
C8—C7—B2 | 120.5 (3) | O5—C23—N2 | 127.8 (9) |
C12—C7—B2 | 122.5 (3) | O5—C23—H23 | 116.8 |
C7—C8—C9 | 121.1 (3) | N2—C23—H23 | 115.5 |
C7—C8—H8 | 119.5 | N2—C24—H24 | 109.3 |
C9—C8—H8 | 119.4 | N2—C24—H25 | 108.8 |
C8—C9—C10 | 119.9 (3) | N2—C24—H26 | 109.2 |
C8—C9—H9 | 120.0 | H24—C24—H25 | 109.4 |
C10—C9—H9 | 120.1 | H24—C24—H26 | 110.1 |
C9—C10—C11 | 120.4 (3) | H25—C24—H26 | 110.0 |
C9—C10—H10 | 119.9 | N2—C25—H27 | 110.1 |
C11—C10—H10 | 119.7 | N2—C25—H28 | 110.4 |
C10—C11—C12 | 120.2 (3) | N2—C25—H29 | 110.0 |
C10—C11—H11 | 119.9 | H27—C25—H28 | 108.6 |
C12—C11—H11 | 119.9 | H27—C25—H29 | 108.7 |
C7—C12—C11 | 121.5 (3) | H28—C25—H29 | 109.0 |
C7—C12—H12 | 119.2 | O1—B1—O3 | 109.9 (2) |
C11—C12—H12 | 119.3 | O1—B1—O4 | 108.3 (2) |
C14—C13—C18 | 116.7 (3) | O1—B1—C1 | 111.8 (2) |
C14—C13—B3 | 122.4 (2) | O3—B1—O4 | 108.5 (2) |
C18—C13—B3 | 120.9 (2) | O3—B1—C1 | 112.4 (3) |
C13—C14—C15 | 120.7 (3) | O4—B1—C1 | 105.6 (2) |
C13—C14—H14 | 119.6 | O1—B2—O2 | 120.9 (2) |
C15—C14—H14 | 119.7 | O1—B2—C7 | 119.9 (3) |
C14—C15—C16 | 120.7 (3) | O2—B2—C7 | 119.2 (2) |
C14—C15—H15 | 119.4 | O2—B3—O3 | 120.4 (3) |
C16—C15—H15 | 119.8 | O2—B3—C13 | 119.2 (2) |
C15—C16—C17 | 119.8 (3) | O3—B3—C13 | 120.4 (2) |
O1—B1—O3—B3 | 25.3 (4) | C1—B1—O3—B3 | −99.9 (3) |
O1—B1—O4—N1 | 67.3 (3) | C2—C1—C6—C5 | −1.7 (5) |
O1—B1—C1—C2 | −138.4 (3) | C2—C3—C4—C5 | −2.2 (7) |
O1—B1—C1—C6 | 40.0 (4) | C3—C2—C1—C6 | 0.4 (5) |
O1—B2—O2—B3 | 9.0 (4) | C3—C2—C1—B1 | 178.8 (3) |
O1—B2—C7—C8 | 5.7 (5) | C3—C4—C5—C6 | 0.9 (8) |
O1—B2—C7—C12 | −176.1 (3) | C5—C6—C1—B1 | 179.9 (4) |
O2—B2—O1—B1 | 7.6 (4) | C7—C8—C9—C10 | 1.4 (6) |
O2—B2—C7—C8 | −172.6 (3) | C7—C12—C11—C10 | 2.1 (7) |
O2—B2—C7—C12 | 5.6 (5) | C7—B2—O1—B1 | −170.7 (3) |
O2—B3—O3—B1 | −11.7 (4) | C7—B2—O2—B3 | −172.8 (2) |
O2—B3—C13—C14 | 5.9 (4) | C8—C7—C12—C11 | −1.1 (6) |
O2—B3—C13—C18 | −174.9 (3) | C8—C9—C10—C11 | −0.4 (7) |
O3—B1—O1—B2 | −23.2 (4) | C9—C8—C7—C12 | −0.6 (5) |
O3—B1—O4—N1 | −52.1 (3) | C9—C8—C7—B2 | 177.7 (3) |
O3—B1—C1—C2 | −14.2 (4) | C9—C10—C11—C12 | −1.3 (7) |
O3—B1—C1—C6 | 164.2 (3) | C11—C12—C7—B2 | −179.4 (4) |
O3—B3—O2—B2 | −6.9 (4) | C13—C14—C15—C16 | 0.3 (6) |
O3—B3—C13—C14 | −174.0 (3) | C13—C18—C17—C16 | 1.0 (7) |
O3—B3—C13—C18 | 5.2 (4) | C13—B3—O2—B2 | 173.1 (2) |
O4—N1—C19—C20 | −67.7 (5) | C13—B3—O3—B1 | 168.3 (3) |
O4—N1—C21—C22 | −64.3 (9) | C14—C13—C18—C17 | −1.7 (5) |
O4—B1—O1—B2 | −141.7 (3) | C14—C15—C16—C17 | −1.0 (7) |
O4—B1—O3—B3 | 143.7 (3) | C15—C14—C13—C18 | 1.0 (5) |
O4—B1—C1—C2 | 104.0 (3) | C15—C14—C13—B3 | −179.7 (3) |
O4—B1—C1—C6 | −77.7 (3) | C15—C16—C17—C18 | 0.4 (7) |
O5—C23—N2—C24 | 176.3 (7) | C17—C18—C13—B3 | 179.0 (3) |
O5—C23—N2—C25 | 0 (1) | C19—N1—O4—B1 | 133.5 (3) |
N1—O4—B1—C1 | −172.8 (2) | C19—N1—C21—C22 | 61 (1) |
C1—C2—C3—C4 | 1.6 (6) | C20—C19—N1—C21 | 166.0 (5) |
C1—C6—C5—C4 | 1.1 (7) | C21—N1—O4—B1 | −98.9 (4) |
C1—B1—O1—B2 | 102.4 (3) |
Symmetry code: (i) −x+1, −y+1, −z+2. |