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Three new blue-luminescent complexes of selected imidazo[1,2-a]pyridine derivatives and 1,2-phenyl­ene­diboronic acid have been synthesized and structurally characterized using single-crystal X-ray diffraction. Additionally, the crystal structures of two of the (N,O)-donor compounds have been evaluated for the first time. The crystal packing and molecular motifs observed in the studied crystals have been thoroughly analysed, including computational studies, and are also discussed within the context of analogous systems reported in the literature. It appears that the new compounds form different crystal networks with regard to the asymmetric unit content and packing, although some similarities can be found. In all cases a typical centrosymmetric dimer bound via boronic acid groups is formed, characterized by an interaction energy of about −80 kJ mol−1, while the 2-(2′-hy­droxy­phenyl)­imidazo[1,2-a]pyridine complex and its meth­oxy derivative form solvate structures, somewhat resembling the previously studied 8-oxy­quinolinate analogues. As far as the spectroscopic properties are concerned, the lowest energy excitation observed in the studied complexes is based on the highest occupied molecular orbital–lowest unoccupied molecular orbital transition, and both these molecular orbitals are centred predominantly on the (N,O)-donor species according to the results of time-dependent density functional theory. Thus, the charge transfer observed for the 8-oxyquinolinate equivalents does not occur in these cases. Consequently, the spectroscopic behaviour of the series is very much comparable with that of the parent imidazo[1,2-a]pyridine derivatives, if the excited-state intramolecular proton-transfer process does not take place, as shown by the absorption and emission spectra collected in toluene and acetone solutions. Complexation causes a reduction in the Stokes shift compared with the respective (N,O)-donor molecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520618015469/dk5074sup1.cif
Contains datablocks global, b, c, odba-a, odba-b, odba-d

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618015469/dk5074bsup2.hkl
Contains datablock b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618015469/dk5074csup3.hkl
Contains datablock c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618015469/dk5074odba-asup4.hkl
Contains datablock odba-a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618015469/dk5074odba-bsup5.hkl
Contains datablock odba-b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618015469/dk5074odba-dsup6.hkl
Contains datablock odba-d

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520618015469/dk5074sup7.pdf
Additional text, figures and tables

CCDC references: 1846570; 1846571; 1846572; 1846573; 1846574

Computing details top

(b) top
Crystal data top
C14H12N2O2F(000) = 1008
Mr = 240.3Dx = 1.412 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2abCell parameters from 9422 reflections
a = 14.5448 (2) Åθ = 3.7–76.9°
b = 6.5214 (4) ŵ = 0.79 mm1
c = 23.8246 (6) ÅT = 100 K
V = 2259.82 (15) Å3Block, colourless
Z = 80.20 × 0.14 × 0.11 mm
Data collection top
Bruker D8 VENTURE
diffractometer
2331 independent reflections
Radiation source: microfocus source1831 reflections with I > 3σ(I)
Multi-layer optics monochromatorRint = 0.042
φ or ω oscillation scansθmax = 77.4°, θmin = 3.7°
Absorption correction: multi-scan
Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015
h = 1618
Tmin = 0.690, Tmax = 0.754k = 78
18355 measured reflectionsl = 3020
Refinement top
Refinement on F2600 constraints
R[F2 > 2σ(F2)] = 0.033All H-atom parameters refined
wR(F2) = 0.075Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.70(Δ/σ)max = 0.015
2331 reflectionsΔρmax = 0.25 e Å3
199 parametersΔρmin = 0.32 e Å3
12 restraints
Special details top

Refinement. TAAM refinement done with JANA program Petricek, V.; Dusek, M.; Palatinus, L., Crystallographic Computing System Jana2006: General Features. Z. Kristallogr. 2014, 229, 345

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.04817 (7)0.30245 (14)0.10446 (4)0.0191 (3)
O20.12775 (7)0.28056 (14)0.09012 (4)0.0197 (3)
N10.10048 (7)0.61288 (17)0.16520 (4)0.0164 (3)
N20.14932 (7)0.93075 (16)0.18284 (4)0.0160 (3)
C10.11032 (8)0.7527 (2)0.20507 (6)0.0167 (4)
C20.09013 (9)0.7473 (2)0.26316 (6)0.0211 (4)
C30.11129 (9)0.9131 (2)0.29580 (6)0.0224 (4)
C40.15087 (10)1.0921 (2)0.27128 (6)0.0224 (4)
C50.16851 (9)1.0995 (2)0.21510 (6)0.0202 (4)
C60.16468 (9)0.8963 (2)0.12662 (5)0.0157 (4)
C70.13363 (9)0.69904 (19)0.11647 (5)0.0143 (4)
C80.13111 (8)0.58662 (19)0.06352 (5)0.0137 (4)
C90.17093 (9)0.66836 (19)0.01462 (6)0.0154 (4)
C100.16879 (9)0.5650 (2)0.03598 (5)0.0158 (4)
C110.12562 (9)0.37264 (19)0.03903 (5)0.0152 (4)
C120.08560 (9)0.2877 (2)0.00845 (5)0.0152 (4)
C130.08811 (8)0.3931 (2)0.05965 (5)0.0148 (4)
C140.08758 (11)0.0821 (2)0.09476 (6)0.0230 (4)
H20.0578 (9)0.6088 (12)0.2786 (6)0.0253*
H30.0983 (10)0.913 (2)0.34054 (14)0.0269*
H40.1692 (9)1.2211 (14)0.2976 (5)0.0269*
H50.1954 (9)1.2334 (13)0.1938 (5)0.0242*
H60.1945 (8)1.0110 (15)0.0993 (4)0.0188*
H90.2060 (8)0.8147 (10)0.0166 (6)0.0185*
H100.2018 (8)0.627 (2)0.0730 (3)0.0189*
H120.0532 (8)0.1383 (9)0.0075 (5)0.0182*
H14a0.1024 (9)0.035 (2)0.1371 (2)0.0276*
H14b0.1219 (9)0.0249 (18)0.0674 (5)0.0276*
H14c0.0148 (2)0.085 (2)0.0867 (6)0.0276*
H150.0603 (12)0.395 (2)0.1366 (5)0.0286*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0229 (5)0.0157 (5)0.0186 (5)0.0042 (4)0.0044 (4)0.0019 (4)
O20.0247 (5)0.0184 (5)0.0161 (5)0.0009 (4)0.0015 (4)0.0009 (4)
N10.0187 (6)0.0157 (6)0.0148 (5)0.0019 (4)0.0019 (4)0.0017 (4)
N20.0146 (5)0.0156 (5)0.0177 (6)0.0003 (4)0.0002 (4)0.0005 (4)
C10.0160 (6)0.0181 (7)0.0159 (7)0.0016 (5)0.0022 (5)0.0012 (5)
C20.0204 (7)0.0278 (8)0.0151 (7)0.0016 (6)0.0028 (6)0.0008 (6)
C30.0208 (7)0.0299 (8)0.0166 (7)0.0009 (6)0.0016 (6)0.0027 (6)
C40.0212 (7)0.0259 (8)0.0202 (7)0.0024 (6)0.0007 (6)0.0063 (6)
C50.0208 (7)0.0191 (7)0.0207 (7)0.0035 (6)0.0020 (5)0.0037 (6)
C60.0165 (6)0.0140 (7)0.0165 (6)0.0028 (5)0.0008 (5)0.0019 (5)
C70.0149 (6)0.0138 (6)0.0142 (6)0.0001 (5)0.0010 (5)0.0013 (5)
C80.0137 (6)0.0122 (6)0.0152 (6)0.0017 (5)0.0000 (5)0.0020 (5)
C90.0169 (6)0.0145 (6)0.0149 (6)0.0027 (5)0.0007 (5)0.0018 (5)
C100.0175 (6)0.0152 (6)0.0146 (6)0.0008 (5)0.0004 (5)0.0013 (5)
C110.0163 (6)0.0145 (6)0.0147 (6)0.0003 (5)0.0009 (5)0.0006 (5)
C120.0173 (6)0.0134 (6)0.0149 (7)0.0018 (5)0.0005 (5)0.0015 (5)
C130.0152 (6)0.0138 (6)0.0155 (6)0.0005 (5)0.0002 (5)0.0011 (5)
C140.0306 (8)0.0201 (7)0.0183 (7)0.0021 (6)0.0024 (6)0.0015 (6)
Geometric parameters (Å, º) top
O1—C131.3514 (15)C3—C41.4268 (19)
O2—C111.3574 (15)C4—C51.364 (2)
O2—C141.4244 (15)C6—C71.3849 (18)
N1—C11.3244 (18)C7—C81.4593 (17)
N1—C71.3768 (16)C8—C91.4064 (18)
N2—C11.3964 (18)C8—C131.4114 (18)
N2—C51.3713 (18)C9—C101.3816 (19)
N2—C61.3763 (15)C10—C111.4049 (19)
C1—C21.415 (2)C11—C121.3874 (17)
C2—C31.3669 (19)C12—C131.4006 (17)
C11—O2—C14117.51 (10)N1—C7—C8121.01 (12)
C1—N1—C7106.63 (12)C6—C7—C8128.74 (11)
C1—N2—C5122.51 (11)C7—C8—C9121.02 (12)
C1—N2—C6107.43 (11)C7—C8—C13121.12 (11)
C5—N2—C6130.04 (12)C9—C8—C13117.86 (11)
N1—C1—N2110.13 (12)C8—C9—C10121.91 (12)
N1—C1—C2131.44 (12)C9—C10—C11119.41 (11)
N2—C1—C2118.42 (12)O2—C11—C10115.53 (11)
C1—C2—C3119.34 (12)O2—C11—C12124.35 (11)
C2—C3—C4120.34 (13)C10—C11—C12120.11 (11)
C3—C4—C5120.44 (12)C11—C12—C13120.22 (12)
N2—C5—C4118.92 (12)O1—C13—C8121.98 (11)
N2—C6—C7105.57 (11)O1—C13—C12117.53 (11)
N1—C7—C6110.23 (11)C8—C13—C12120.49 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H15···N10.990 (12)1.682 (13)2.6020 (14)152.7 (11)
O1—H15···C70.990 (12)2.304 (13)2.8832 (15)116.4 (9)
(c) top
Crystal data top
C13H9BrN2OF(000) = 576
Mr = 289.1Dx = 1.747 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9928 reflections
a = 12.8423 (7) Åθ = 3.3–30.5°
b = 7.0971 (4) ŵ = 3.72 mm1
c = 12.6239 (7) ÅT = 100 K
β = 107.1883 (16)°Plate, colourless
V = 1099.19 (11) Å30.22 × 0.19 × 0.12 mm
Z = 4
Data collection top
Bruker D8 VENTURE
diffractometer
3358 independent reflections
Radiation source: sealed-tube2530 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.044
φ or ω oscillation scansθmax = 30.6°, θmin = 3.3°
Absorption correction: multi-scan
Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015
h = 1818
Tmin = 0.65, Tmax = 0.746k = 1010
29038 measured reflectionsl = 1818
Refinement top
Refinement on F2541 constraints
R[F2 > 2σ(F2)] = 0.025All H-atom parameters refined
wR(F2) = 0.050Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.21(Δ/σ)max = 0.010
3358 reflectionsΔρmax = 0.56 e Å3
181 parametersΔρmin = 0.45 e Å3
9 restraints
Special details top

Refinement. TAAM refinement done with JANA program Petricek, V.; Dusek, M.; Palatinus, L., Crystallographic Computing System Jana2006: General Features. Z. Kristallogr. 2014, 229, 345

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.024615 (12)0.82947 (2)0.394802 (12)0.02217 (5)
O10.38303 (8)0.52590 (14)0.78020 (8)0.0189 (3)
N10.52718 (10)0.60478 (16)0.67938 (10)0.0153 (4)
N20.59074 (10)0.72289 (15)0.54704 (9)0.0144 (4)
C10.61605 (12)0.62819 (18)0.64821 (12)0.0147 (5)
C20.72582 (12)0.5737 (2)0.69912 (12)0.0187 (5)
C30.80275 (13)0.6186 (2)0.64809 (13)0.0212 (5)
C40.77407 (13)0.7191 (2)0.54545 (13)0.0207 (5)
C50.66814 (12)0.7680 (2)0.49653 (12)0.0177 (5)
C60.48141 (12)0.7597 (2)0.51468 (11)0.0141 (4)
C70.44317 (12)0.68606 (18)0.59776 (11)0.0136 (4)
C80.33092 (11)0.68371 (18)0.60273 (11)0.0132 (4)
C90.24601 (12)0.7562 (2)0.51538 (12)0.0155 (4)
C100.13902 (12)0.7443 (2)0.51817 (12)0.0171 (5)
C110.11366 (12)0.6615 (2)0.60756 (13)0.0194 (5)
C120.19715 (13)0.5897 (2)0.69474 (12)0.0183 (5)
C130.30551 (12)0.59955 (19)0.69338 (11)0.0153 (5)
H20.7450 (12)0.499 (2)0.7773 (7)0.0224*
H30.8874 (4)0.581 (2)0.6856 (12)0.0254*
H40.8351 (10)0.757 (2)0.5055 (12)0.0248*
H50.6383 (12)0.8372 (18)0.4168 (6)0.0213*
H60.4397 (11)0.8335 (17)0.4390 (7)0.0169*
H90.2633 (12)0.8218 (18)0.4449 (8)0.0186*
H110.0305 (5)0.654 (2)0.6108 (13)0.0233*
H120.1741 (11)0.530 (2)0.7635 (8)0.022*
H130.4517 (8)0.526 (3)0.7592 (15)0.0283*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01409 (8)0.03204 (9)0.01871 (8)0.00325 (7)0.00223 (6)0.00481 (7)
O10.0236 (6)0.0188 (5)0.0138 (5)0.0002 (5)0.0050 (4)0.0025 (4)
N10.0169 (6)0.0145 (6)0.0137 (6)0.0001 (5)0.0032 (5)0.0015 (5)
N20.0172 (6)0.0117 (5)0.0141 (6)0.0018 (5)0.0042 (5)0.0016 (5)
C10.0163 (8)0.0120 (7)0.0143 (7)0.0003 (5)0.0022 (6)0.0005 (5)
C20.0167 (8)0.0190 (8)0.0188 (8)0.0023 (6)0.0029 (6)0.0014 (6)
C30.0164 (8)0.0236 (8)0.0224 (8)0.0015 (6)0.0040 (6)0.0041 (6)
C40.0189 (8)0.0217 (8)0.0234 (8)0.0011 (6)0.0091 (6)0.0030 (6)
C50.0185 (8)0.0173 (7)0.0177 (7)0.0011 (6)0.0060 (6)0.0007 (6)
C60.0173 (8)0.0128 (6)0.0119 (7)0.0014 (6)0.0037 (6)0.0017 (5)
C70.0154 (7)0.0116 (6)0.0127 (6)0.0008 (5)0.0024 (5)0.0004 (5)
C80.0157 (7)0.0111 (6)0.0127 (6)0.0009 (5)0.0038 (5)0.0006 (5)
C90.0148 (7)0.0166 (7)0.0143 (7)0.0008 (6)0.0030 (6)0.0019 (6)
C100.0154 (8)0.0186 (7)0.0167 (7)0.0010 (6)0.0038 (6)0.0001 (6)
C110.0172 (8)0.0221 (7)0.0200 (7)0.0002 (6)0.0072 (6)0.0016 (6)
C120.0189 (8)0.0200 (7)0.0179 (8)0.0010 (6)0.0083 (6)0.0014 (6)
C130.0190 (8)0.0130 (6)0.0140 (7)0.0011 (6)0.0048 (6)0.0001 (5)
Geometric parameters (Å, º) top
Br1—C101.8967 (11)C4—C51.3631 (17)
O1—C131.3494 (14)C6—C71.385 (2)
N1—C11.324 (2)C7—C81.4618 (19)
N1—C71.3788 (16)C8—C91.3993 (16)
N2—C11.3938 (17)C8—C131.412 (2)
N2—C51.368 (2)C9—C101.3876 (19)
N2—C61.3662 (18)C10—C111.393 (2)
C1—C21.4185 (17)C11—C121.3856 (16)
C2—C31.366 (2)C12—C131.3988 (19)
C3—C41.4294 (18)
C1—N1—C7106.16 (12)C6—C7—C8127.68 (11)
C1—N2—C5122.30 (11)C7—C8—C9120.75 (12)
C1—N2—C6107.91 (12)C7—C8—C13120.42 (10)
C5—N2—C6129.77 (12)C9—C8—C13118.76 (12)
N1—C1—N2110.14 (11)C8—C9—C10120.30 (13)
N1—C1—C2131.26 (12)Br1—C10—C9119.48 (10)
N2—C1—C2118.60 (13)Br1—C10—C11119.36 (9)
C1—C2—C3118.84 (12)C9—C10—C11121.07 (11)
C2—C3—C4121.06 (11)C10—C11—C12119.16 (12)
C3—C4—C5119.50 (13)C11—C12—C13120.72 (13)
N2—C5—C4119.68 (12)O1—C13—C8122.03 (12)
N2—C6—C7105.32 (11)O1—C13—C12117.97 (12)
N1—C7—C6110.47 (12)C8—C13—C12119.99 (11)
N1—C7—C8121.83 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i1.083 (10)2.162 (10)3.2349 (15)170.1 (11)
O1—H13···N10.994 (12)1.685 (14)2.5987 (18)150.8 (14)
O1—H13···C70.994 (12)2.305 (15)2.8711 (18)115.1 (10)
Symmetry code: (i) x, y+3/2, z1/2.
(odba-a) top
Crystal data top
C19H14B2N2O3·C3H6OF(000) = 1664
Mr = 398.02Dx = 1.321 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 99881 reflections
a = 10.7147 (11) Åθ = 2.2–29.8°
b = 34.282 (3) ŵ = 0.09 mm1
c = 10.9168 (11) ÅT = 100 K
β = 93.176 (2)°Block, colourless
V = 4003.8 (7) Å30.29 × 0.13 × 0.06 mm
Z = 8
Data collection top
Bruker D8 VENTURE
diffractometer
21060 independent reflections
Radiation source: sealed-tube9603 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.135
φ or ω oscillation scansθmax = 29.8°, θmin = 2.2°
Absorption correction: multi-scan
Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015
h = 1413
Tmin = 0.650, Tmax = 0.746k = 4747
99881 measured reflectionsl = 1414
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.055Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
wR(F2) = 0.102(Δ/σ)max = 0.027
S = 1.19Δρmax = 0.76 e Å3
21060 reflectionsΔρmin = 0.71 e Å3
1093 parametersAbsolute structure: 10020 of Friedel pairs used in the refinement
4 restraintsAbsolute structure parameter: 0.5 (7)
4229 constraints
Special details top

Refinement. TAAM refinement done with JANA program Petricek, V.; Dusek, M.; Palatinus, L., Crystallographic Computing System Jana2006: General Features. Z. Kristallogr. 2014, 229, 345

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.5650 (2)0.68486 (8)0.4050 (2)0.0108 (10)
N20.7015 (3)0.71855 (8)0.3033 (3)0.0148 (10)
O10.57633 (19)0.63517 (6)0.56932 (18)0.0139 (7)
O20.3829 (2)0.67039 (6)0.52069 (19)0.0151 (8)
O30.6553 (2)0.57292 (6)0.6357 (2)0.0213 (8)
B10.4913 (4)0.65183 (11)0.4690 (3)0.0128 (13)
B20.5882 (4)0.59542 (11)0.5536 (4)0.0168 (13)
C10.6506 (3)0.68188 (9)0.3197 (3)0.0141 (11)
C20.6922 (3)0.65052 (10)0.2493 (3)0.0199 (13)
C30.7802 (3)0.65753 (10)0.1660 (3)0.0201 (12)
C40.8322 (3)0.69524 (10)0.1526 (3)0.0211 (12)
C50.7909 (3)0.72538 (10)0.2221 (3)0.0193 (12)
C60.6435 (3)0.74444 (10)0.3787 (3)0.0160 (12)
C70.5594 (3)0.72356 (10)0.4401 (3)0.0118 (11)
C80.4712 (3)0.73475 (10)0.5289 (3)0.0129 (12)
C90.4655 (3)0.77270 (9)0.5762 (3)0.0194 (12)
C100.3747 (3)0.78317 (10)0.6542 (3)0.0211 (13)
C110.2876 (3)0.75559 (10)0.6884 (3)0.0214 (13)
C120.2919 (3)0.71757 (10)0.6449 (3)0.0166 (12)
C130.3840 (3)0.70663 (9)0.5658 (3)0.0138 (11)
C140.5151 (3)0.58196 (9)0.4346 (3)0.0139 (11)
C150.5017 (3)0.54593 (9)0.3744 (3)0.0158 (11)
C160.4282 (3)0.54349 (9)0.2655 (3)0.0190 (12)
C170.3694 (3)0.57659 (10)0.2157 (3)0.0208 (12)
C180.3848 (3)0.61273 (9)0.2750 (3)0.0193 (12)
C190.4555 (3)0.61533 (9)0.3841 (3)0.0132 (11)
H20.6551940.6214350.2609350.0239*
H30.8107390.6338540.1092560.0242*
H40.9037930.7001480.0880360.0254*
H50.8291360.7543990.2126530.0231*
H60.6616440.7754230.3871050.0192*
H90.5338530.7941130.5510440.0233*
H100.3707710.8127330.6887570.0253*
H110.2159110.7638840.7495090.0257*
H120.2239140.6963760.6723980.02*
H150.5482390.5202310.41230.019*
H160.4166360.5156870.2191470.0228*
H170.3119020.5744310.1312050.0249*
H180.3411510.6385920.2350640.0232*
H3o0.707 (3)0.5883 (9)0.695 (3)0.0319*
N31.0826 (3)0.52836 (8)0.6940 (3)0.0131 (10)
N40.9665 (2)0.56530 (8)0.8101 (2)0.0106 (9)
O40.7608 (2)0.67766 (6)0.68289 (19)0.0151 (8)
O50.8397 (2)0.58276 (6)0.9799 (2)0.0160 (8)
O60.80577 (18)0.61667 (5)0.78490 (18)0.0127 (7)
B30.8996 (4)0.59972 (10)0.8759 (4)0.0123 (12)
B40.8329 (3)0.65531 (11)0.7624 (3)0.0116 (12)
C201.0590 (3)0.56631 (9)0.7320 (3)0.0130 (11)
C211.1283 (3)0.59720 (10)0.6856 (3)0.0177 (12)
C221.2201 (3)0.58897 (10)0.6061 (3)0.0240 (13)
C231.2425 (3)0.54977 (10)0.5708 (3)0.0226 (13)
C241.1735 (3)0.52016 (9)0.6154 (3)0.0171 (12)
C251.0020 (3)0.50372 (10)0.7506 (3)0.0142 (11)
C260.9313 (3)0.52655 (9)0.8215 (3)0.0112 (11)
C270.8368 (3)0.51683 (10)0.9052 (3)0.0117 (12)
C280.7909 (3)0.47883 (9)0.9170 (3)0.0160 (11)
C290.7030 (3)0.47008 (11)0.9996 (3)0.0212 (13)
C300.6586 (3)0.49941 (10)1.0751 (3)0.0198 (12)
C310.7043 (3)0.53740 (10)1.0657 (3)0.0195 (13)
C320.7931 (3)0.54636 (10)0.9813 (3)0.0144 (11)
C330.9488 (3)0.66851 (8)0.8425 (3)0.0127 (11)
C340.9894 (3)0.63547 (9)0.9102 (3)0.0116 (10)
C351.0961 (3)0.63834 (9)0.9892 (3)0.0156 (11)
C361.1614 (3)0.67377 (9)1.0005 (3)0.0152 (11)
C371.1199 (3)0.70627 (10)0.9334 (3)0.0199 (12)
C381.0142 (3)0.70367 (9)0.8546 (3)0.0144 (11)
H211.1097790.6270180.7119530.0213*
H221.2753160.6123930.5704380.0288*
H231.3147850.543440.5081590.0271*
H241.1906520.4903080.5885570.0205*
H250.9961160.4723380.7404710.017*
H280.8255250.4558740.8597450.0192*
H290.6681160.4405531.0063570.0255*
H300.5892750.492691.1403920.0238*
H310.6704850.5600841.1243990.0234*
H351.1285470.6131751.0418570.0187*
H361.2442810.6758421.0615610.0182*
H371.1702020.73360.9426940.0239*
H380.9822140.7289610.8023890.0173*
H4o0.693 (2)0.6635 (9)0.638 (3)0.0226*
N50.5261 (3)0.47235 (8)0.7445 (3)0.0154 (10)
N60.4157 (2)0.43525 (7)0.8638 (2)0.0121 (9)
O70.26247 (19)0.38230 (6)0.82645 (18)0.0125 (7)
O80.2815 (2)0.41484 (6)1.02494 (19)0.0153 (7)
O90.2297 (2)0.32245 (6)0.7176 (2)0.0152 (8)
B50.3498 (4)0.39929 (10)0.9228 (4)0.0124 (13)
B60.2925 (4)0.34415 (10)0.8043 (3)0.0131 (13)
C390.5057 (3)0.43479 (10)0.7821 (3)0.0147 (12)
C400.5775 (3)0.40404 (10)0.7362 (3)0.0195 (12)
C410.6643 (3)0.41278 (10)0.6524 (3)0.0171 (12)
C420.6816 (3)0.45193 (10)0.6144 (3)0.0236 (13)
C430.6132 (3)0.48134 (11)0.6628 (3)0.0201 (13)
C440.4477 (3)0.49616 (10)0.8045 (3)0.0162 (12)
C450.3781 (3)0.47365 (10)0.8776 (3)0.0147 (12)
C460.2790 (3)0.48174 (9)0.9593 (3)0.0137 (11)
C470.2290 (3)0.51913 (9)0.9701 (3)0.0163 (12)
C480.1346 (3)0.52610 (9)1.0481 (3)0.0174 (12)
C490.0889 (3)0.49519 (10)1.1181 (3)0.0205 (12)
C500.1384 (3)0.45812 (9)1.1095 (3)0.0199 (12)
C510.2342 (3)0.45101 (10)1.0295 (3)0.0166 (12)
C520.4058 (3)0.33132 (9)0.8893 (3)0.0132 (11)
C530.4410 (3)0.36437 (9)0.9615 (3)0.0123 (11)
C540.5438 (3)0.36245 (9)1.0443 (3)0.0158 (11)
C550.6153 (3)0.32821 (10)1.0559 (3)0.0173 (11)
C560.5802 (3)0.29566 (9)0.9845 (3)0.0168 (12)
C570.4767 (3)0.29685 (9)0.9014 (3)0.0183 (12)
H400.5643540.3742990.7663290.0233*
H410.7197670.3896980.615050.0205*
H420.7490290.4585540.5469810.0284*
H430.6281770.5113670.6365340.0241*
H440.4417590.5275740.7955730.0194*
H470.2648320.542870.9168290.0196*
H480.0957640.5551131.0554560.0208*
H490.0143710.500541.1790040.0246*
H500.1034770.4346131.1643720.0239*
H540.5691990.3875851.1003990.019*
H550.6965790.3269661.1193250.0207*
H560.634530.2690790.9939580.0201*
H570.4509620.2714420.8467330.0219*
H9o0.157 (2)0.3367 (9)0.681 (3)0.0229*
N70.0112 (2)0.31365 (7)0.4504 (2)0.0098 (9)
N80.1474 (3)0.27917 (7)0.3486 (3)0.0144 (10)
O100.04092 (19)0.36405 (6)0.60880 (18)0.0123 (7)
O110.1348 (2)0.42562 (6)0.66171 (19)0.0167 (8)
O120.1602 (2)0.33060 (6)0.57772 (19)0.0156 (7)
B70.0541 (4)0.34770 (10)0.5178 (4)0.0102 (12)
B80.0550 (4)0.40347 (10)0.5899 (3)0.0123 (12)
C580.0976 (3)0.31583 (9)0.3645 (3)0.0119 (12)
C590.1390 (3)0.34725 (9)0.2941 (3)0.0144 (11)
C600.2288 (3)0.34038 (10)0.2122 (3)0.0173 (12)
C610.2795 (3)0.30206 (10)0.1990 (3)0.0211 (13)
C620.2366 (3)0.27220 (10)0.2686 (3)0.0161 (12)
C630.0912 (3)0.25402 (9)0.4270 (3)0.0125 (11)
C640.0074 (3)0.27522 (9)0.4903 (3)0.0128 (12)
C650.0810 (3)0.26481 (9)0.5800 (3)0.0124 (11)
C660.0908 (3)0.22639 (10)0.6222 (3)0.0173 (12)
C670.1810 (3)0.21695 (10)0.7024 (3)0.0241 (13)
C680.2636 (3)0.24530 (10)0.7416 (3)0.0201 (13)
C690.2527 (3)0.28328 (10)0.6998 (3)0.0199 (12)
C700.1625 (3)0.29366 (10)0.6198 (3)0.0151 (12)
C710.0297 (3)0.41745 (9)0.4797 (3)0.0123 (11)
C720.0959 (3)0.38424 (9)0.4350 (3)0.0124 (11)
C730.1830 (3)0.38805 (9)0.3370 (3)0.0164 (11)
C740.2061 (3)0.42456 (9)0.2835 (3)0.0199 (11)
C750.1393 (3)0.45757 (9)0.3268 (3)0.0188 (12)
C760.0517 (3)0.45400 (9)0.4237 (3)0.0178 (12)
H590.1006830.3762140.3045790.0172*
H600.2616360.3641080.1569240.0208*
H610.350990.2967440.1346560.0253*
H620.2740460.2430720.2595790.0194*
H630.1098810.2230980.4369480.015*
H660.0276470.2041680.5918230.0208*
H670.1878950.1872750.7353590.029*
H680.3350830.2377130.803760.0242*
H690.316280.3053340.730470.0239*
H730.2333220.3626590.3017580.0197*
H740.2757140.4274560.2083110.0238*
H750.1566010.4857240.2842520.0226*
H760.0002560.4793560.456750.0214*
H11o0.177 (3)0.4128 (10)0.733 (2)0.025*
O130.4642 (2)0.69217 (7)0.0773 (2)0.0279 (9)
C770.5040 (3)0.68147 (10)0.0185 (3)0.0217 (13)
C780.5724 (4)0.70845 (11)0.0996 (3)0.0379 (16)
C790.4907 (4)0.64038 (10)0.0632 (3)0.0491 (18)
O140.9242 (3)0.63590 (8)0.4737 (2)0.0551 (12)
C800.9497 (4)0.60851 (12)0.4117 (4)0.0339 (14)
C810.8932 (4)0.56969 (12)0.4284 (5)0.060 (2)
C821.0399 (4)0.61136 (13)0.3128 (4)0.070 (2)
O150.0843 (2)0.30769 (7)0.1202 (2)0.0268 (9)
C830.0458 (3)0.32067 (10)0.0268 (4)0.0268 (14)
C840.0246 (3)0.29524 (11)0.0574 (3)0.0351 (15)
C850.0653 (4)0.36248 (11)0.0118 (4)0.0518 (18)
O160.4803 (2)0.44236 (7)1.2607 (2)0.0403 (10)
C860.4357 (3)0.42619 (10)1.3456 (3)0.0264 (13)
C870.4713 (3)0.38551 (11)1.3825 (3)0.0349 (15)
C880.3415 (4)0.44557 (10)1.4201 (4)0.0445 (16)
H78a0.6151260.7315320.0450120.0455*
H78b0.6436940.6924450.1439770.0455*
H78c0.5076670.7207630.1679910.0455*
H79a0.4355230.6399510.1486880.059*
H79b0.5817810.6284020.0767390.059*
H79c0.4450780.6231830.0037980.059*
H81a0.9651860.5477370.4293560.0715*
H81b0.8479160.5690240.5139680.0715*
H81c0.8254890.5640110.3539290.0715*
H82a1.0118780.5917610.2392570.0838*
H82b1.041040.6408060.2784780.0838*
H82c1.1320060.603580.3493170.0838*
H84a0.1227690.3019910.0472140.0421*
H84b0.0102520.2650670.0345930.0421*
H84c0.0087650.3004190.1508790.0421*
H85a0.096550.3635160.1072210.0622*
H85b0.1346890.3756420.0427170.0622*
H85c0.0214610.3781830.0014620.0622*
H87a0.4169120.3764251.4574580.0418*
H87b0.4535590.3661661.3057410.0418*
H87c0.5691850.3846371.4107710.0418*
H88a0.3355920.4760191.3962030.0534*
H88b0.2517150.432021.4019980.0534*
H88c0.3691260.4427011.516040.0534*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0097 (16)0.0109 (17)0.0122 (17)0.0006 (13)0.0028 (14)0.0034 (13)
N20.0173 (18)0.0124 (16)0.0145 (18)0.0022 (14)0.0006 (15)0.0043 (14)
O10.0209 (13)0.0044 (11)0.0164 (12)0.0032 (10)0.0002 (11)0.0013 (10)
O20.0153 (13)0.0089 (12)0.0216 (14)0.0044 (10)0.0057 (11)0.0029 (10)
O30.0320 (16)0.0068 (12)0.0241 (15)0.0009 (11)0.0068 (13)0.0014 (10)
B10.014 (2)0.014 (2)0.011 (2)0.0039 (17)0.0041 (19)0.0001 (17)
B20.017 (2)0.016 (2)0.018 (2)0.0009 (17)0.007 (2)0.0085 (18)
C10.021 (2)0.0063 (18)0.015 (2)0.0039 (15)0.0052 (16)0.0034 (15)
C20.021 (2)0.015 (2)0.025 (2)0.0001 (17)0.0120 (19)0.0055 (17)
C30.020 (2)0.016 (2)0.026 (2)0.0008 (16)0.0103 (18)0.0020 (17)
C40.025 (2)0.017 (2)0.022 (2)0.0003 (17)0.0079 (18)0.0020 (17)
C50.027 (2)0.013 (2)0.020 (2)0.0080 (17)0.0109 (18)0.0047 (17)
C60.024 (2)0.0047 (17)0.020 (2)0.0016 (16)0.0066 (18)0.0011 (15)
C70.012 (2)0.0143 (19)0.009 (2)0.0031 (16)0.0011 (16)0.0020 (16)
C80.012 (2)0.010 (2)0.017 (2)0.0008 (15)0.0025 (17)0.0007 (16)
C90.029 (2)0.0068 (18)0.023 (2)0.0018 (16)0.0059 (19)0.0039 (16)
C100.029 (2)0.012 (2)0.024 (2)0.0012 (18)0.0091 (19)0.0010 (17)
C110.028 (2)0.015 (2)0.023 (2)0.0010 (18)0.0075 (19)0.0065 (17)
C120.017 (2)0.014 (2)0.019 (2)0.0011 (16)0.0046 (17)0.0001 (16)
C130.016 (2)0.0092 (18)0.016 (2)0.0008 (16)0.0009 (16)0.0019 (15)
C140.021 (2)0.0037 (16)0.017 (2)0.0001 (15)0.0062 (17)0.0031 (15)
C150.019 (2)0.0064 (17)0.022 (2)0.0024 (15)0.0013 (17)0.0034 (16)
C160.020 (2)0.0111 (18)0.026 (2)0.0022 (15)0.0014 (18)0.0085 (16)
C170.023 (2)0.0149 (19)0.024 (2)0.0016 (16)0.0032 (17)0.0062 (16)
C180.022 (2)0.0103 (18)0.025 (2)0.0026 (16)0.0006 (17)0.0031 (16)
C190.0142 (19)0.0103 (17)0.0151 (19)0.0008 (15)0.0003 (16)0.0030 (15)
N30.0151 (17)0.0066 (15)0.0177 (17)0.0006 (13)0.0029 (14)0.0007 (13)
N40.0119 (17)0.0063 (15)0.0139 (17)0.0033 (12)0.0047 (14)0.0020 (13)
O40.0196 (14)0.0094 (12)0.0159 (13)0.0000 (10)0.0011 (11)0.0021 (10)
O50.0212 (14)0.0079 (12)0.0194 (14)0.0014 (10)0.0053 (12)0.0010 (10)
O60.0159 (13)0.0032 (11)0.0192 (13)0.0016 (10)0.0033 (11)0.0004 (10)
B30.013 (2)0.011 (2)0.013 (2)0.0017 (17)0.0035 (19)0.0021 (17)
B40.012 (2)0.012 (2)0.012 (2)0.0033 (17)0.0103 (19)0.0023 (17)
C200.018 (2)0.0017 (17)0.020 (2)0.0033 (15)0.0029 (17)0.0041 (15)
C210.023 (2)0.0084 (19)0.022 (2)0.0061 (16)0.0114 (18)0.0001 (16)
C220.026 (2)0.017 (2)0.030 (2)0.0068 (17)0.0143 (19)0.0037 (17)
C230.023 (2)0.0123 (19)0.035 (2)0.0058 (17)0.0160 (18)0.0062 (17)
C240.018 (2)0.0067 (18)0.027 (2)0.0003 (15)0.0042 (18)0.0016 (16)
C250.018 (2)0.0066 (18)0.018 (2)0.0009 (15)0.0049 (17)0.0038 (15)
C260.011 (2)0.0112 (18)0.012 (2)0.0023 (16)0.0011 (16)0.0076 (15)
C270.013 (2)0.010 (2)0.012 (2)0.0013 (15)0.0024 (17)0.0003 (16)
C280.024 (2)0.0085 (18)0.016 (2)0.0018 (16)0.0054 (17)0.0017 (15)
C290.022 (2)0.016 (2)0.025 (2)0.0080 (17)0.0021 (18)0.0059 (17)
C300.019 (2)0.022 (2)0.020 (2)0.0042 (17)0.0039 (17)0.0086 (17)
C310.023 (2)0.013 (2)0.024 (2)0.0015 (17)0.0098 (18)0.0059 (17)
C320.0121 (19)0.0166 (19)0.015 (2)0.0004 (16)0.0045 (16)0.0043 (16)
C330.018 (2)0.0062 (17)0.0139 (19)0.0013 (14)0.0052 (16)0.0003 (14)
C340.0130 (19)0.0109 (17)0.0110 (18)0.0015 (15)0.0011 (15)0.0007 (14)
C350.020 (2)0.0105 (18)0.0159 (19)0.0003 (15)0.0013 (16)0.0003 (15)
C360.019 (2)0.0135 (18)0.0134 (19)0.0038 (15)0.0014 (16)0.0001 (15)
C370.022 (2)0.0143 (19)0.024 (2)0.0047 (16)0.0058 (19)0.0021 (17)
C380.0157 (19)0.0115 (18)0.0160 (19)0.0016 (15)0.0003 (16)0.0034 (15)
N50.0215 (18)0.0105 (16)0.0140 (17)0.0023 (14)0.0009 (14)0.0020 (13)
N60.0180 (17)0.0047 (14)0.0133 (16)0.0001 (12)0.0006 (13)0.0014 (12)
O70.0164 (13)0.0032 (11)0.0178 (13)0.0037 (10)0.0013 (11)0.0001 (10)
O80.0221 (14)0.0064 (12)0.0176 (13)0.0027 (10)0.0040 (11)0.0022 (10)
O90.0169 (14)0.0049 (12)0.0234 (14)0.0009 (9)0.0031 (12)0.0006 (10)
B50.018 (2)0.007 (2)0.012 (2)0.0037 (17)0.0010 (19)0.0025 (17)
B60.019 (2)0.011 (2)0.011 (2)0.0040 (17)0.0070 (19)0.0003 (17)
C390.024 (2)0.0033 (19)0.017 (2)0.0053 (16)0.0035 (18)0.0017 (16)
C400.027 (2)0.0118 (19)0.020 (2)0.0008 (17)0.0058 (18)0.0000 (16)
C410.021 (2)0.0114 (19)0.019 (2)0.0001 (16)0.0084 (17)0.0018 (16)
C420.033 (2)0.020 (2)0.019 (2)0.0057 (19)0.0066 (18)0.0020 (18)
C430.024 (2)0.016 (2)0.021 (2)0.0040 (18)0.0092 (19)0.0041 (17)
C440.023 (2)0.0054 (18)0.019 (2)0.0035 (16)0.0027 (18)0.0005 (16)
C450.015 (2)0.016 (2)0.013 (2)0.0005 (17)0.0022 (17)0.0025 (17)
C460.019 (2)0.0025 (17)0.019 (2)0.0006 (15)0.0003 (17)0.0007 (15)
C470.015 (2)0.0068 (19)0.026 (2)0.0008 (15)0.0073 (18)0.0003 (16)
C480.024 (2)0.0065 (17)0.022 (2)0.0038 (15)0.0025 (18)0.0000 (16)
C490.020 (2)0.0170 (19)0.025 (2)0.0081 (17)0.0026 (17)0.0034 (17)
C500.024 (2)0.0105 (19)0.026 (2)0.0061 (16)0.0052 (18)0.0009 (16)
C510.022 (2)0.0090 (19)0.018 (2)0.0003 (16)0.0025 (18)0.0041 (16)
C520.016 (2)0.0091 (17)0.0147 (19)0.0010 (15)0.0027 (16)0.0009 (14)
C530.0127 (19)0.0123 (18)0.0123 (18)0.0030 (15)0.0031 (16)0.0001 (15)
C540.016 (2)0.0139 (18)0.017 (2)0.0024 (15)0.0027 (17)0.0011 (16)
C550.013 (2)0.0188 (19)0.019 (2)0.0013 (16)0.0041 (16)0.0016 (16)
C560.018 (2)0.0159 (19)0.016 (2)0.0039 (16)0.0028 (17)0.0046 (16)
C570.027 (2)0.0094 (18)0.018 (2)0.0056 (16)0.0018 (18)0.0004 (15)
N70.0195 (17)0.0015 (13)0.0082 (15)0.0002 (12)0.0009 (13)0.0017 (11)
N80.0153 (17)0.0071 (15)0.0211 (18)0.0011 (13)0.0025 (14)0.0043 (13)
O100.0166 (13)0.0060 (11)0.0144 (12)0.0009 (9)0.0019 (10)0.0006 (10)
O110.0220 (14)0.0064 (12)0.0209 (13)0.0001 (10)0.0047 (12)0.0021 (10)
O120.0207 (14)0.0075 (11)0.0189 (13)0.0013 (10)0.0043 (11)0.0019 (10)
B70.011 (2)0.0053 (19)0.015 (2)0.0049 (16)0.0023 (19)0.0011 (16)
B80.012 (2)0.010 (2)0.015 (2)0.0019 (16)0.0057 (18)0.0044 (16)
C580.018 (2)0.0034 (18)0.014 (2)0.0003 (15)0.0013 (17)0.0047 (16)
C590.015 (2)0.0072 (17)0.021 (2)0.0022 (15)0.0018 (17)0.0007 (15)
C600.023 (2)0.013 (2)0.016 (2)0.0010 (16)0.0049 (18)0.0052 (16)
C610.020 (2)0.017 (2)0.027 (2)0.0024 (17)0.0082 (18)0.0004 (18)
C620.022 (2)0.0053 (19)0.022 (2)0.0014 (16)0.0107 (18)0.0033 (17)
C630.019 (2)0.0027 (17)0.016 (2)0.0033 (15)0.0012 (17)0.0053 (15)
C640.020 (2)0.0066 (18)0.011 (2)0.0051 (16)0.0008 (17)0.0006 (15)
C650.020 (2)0.0077 (18)0.0103 (18)0.0012 (15)0.0019 (16)0.0020 (15)
C660.027 (2)0.0078 (19)0.017 (2)0.0009 (17)0.0012 (18)0.0021 (16)
C670.037 (3)0.016 (2)0.019 (2)0.0017 (18)0.0061 (19)0.0103 (17)
C680.019 (2)0.022 (2)0.020 (2)0.0005 (17)0.0059 (18)0.0047 (17)
C690.022 (2)0.018 (2)0.020 (2)0.0035 (17)0.0050 (18)0.0035 (17)
C700.019 (2)0.0120 (19)0.015 (2)0.0021 (16)0.0041 (17)0.0002 (16)
C710.0138 (19)0.0075 (18)0.0159 (19)0.0004 (14)0.0042 (15)0.0026 (15)
C720.0132 (19)0.0088 (17)0.0154 (19)0.0021 (15)0.0013 (16)0.0013 (15)
C730.0173 (19)0.0114 (19)0.020 (2)0.0021 (15)0.0052 (16)0.0028 (15)
C740.023 (2)0.0155 (19)0.020 (2)0.0013 (16)0.0063 (17)0.0061 (16)
C750.024 (2)0.0108 (18)0.021 (2)0.0004 (16)0.0026 (17)0.0107 (16)
C760.023 (2)0.0100 (18)0.021 (2)0.0027 (16)0.0002 (18)0.0044 (16)
O130.0317 (16)0.0294 (16)0.0236 (15)0.0013 (13)0.0104 (13)0.0025 (13)
C770.024 (2)0.018 (2)0.024 (2)0.0032 (17)0.0041 (19)0.0009 (18)
C780.045 (3)0.031 (2)0.039 (3)0.004 (2)0.019 (2)0.004 (2)
C790.062 (4)0.029 (2)0.058 (3)0.010 (2)0.024 (3)0.017 (2)
O140.068 (2)0.0473 (19)0.0502 (19)0.0203 (16)0.0072 (17)0.0142 (16)
C800.035 (2)0.033 (3)0.035 (3)0.007 (2)0.015 (2)0.005 (2)
C810.038 (3)0.046 (3)0.095 (4)0.001 (2)0.007 (3)0.018 (3)
C820.082 (4)0.056 (3)0.077 (4)0.028 (3)0.054 (3)0.030 (3)
O150.0264 (16)0.0281 (16)0.0266 (16)0.0027 (12)0.0086 (13)0.0015 (13)
C830.031 (2)0.018 (2)0.033 (3)0.0042 (18)0.006 (2)0.0007 (19)
C840.036 (3)0.029 (2)0.041 (3)0.001 (2)0.014 (2)0.007 (2)
C850.057 (3)0.028 (2)0.072 (3)0.006 (2)0.020 (3)0.016 (2)
O160.0445 (18)0.0305 (15)0.0477 (18)0.0053 (13)0.0199 (15)0.0040 (14)
C860.030 (2)0.017 (2)0.033 (2)0.0035 (17)0.0093 (19)0.0008 (18)
C870.035 (3)0.025 (2)0.044 (3)0.0037 (19)0.004 (2)0.000 (2)
C880.038 (3)0.028 (2)0.071 (3)0.004 (2)0.029 (2)0.004 (2)
Geometric parameters (Å, º) top
N1—B11.568 (4)C41—H411.0833
N1—C11.347 (4)C42—C431.369 (5)
N1—C71.384 (4)C42—H421.0838
N2—C11.386 (4)C43—H431.0842
N2—C51.361 (5)C44—C451.362 (5)
N2—C61.380 (5)C44—H441.0815
O1—B11.498 (4)C45—C461.450 (5)
O1—B21.381 (4)C46—C471.397 (4)
O2—B11.465 (5)C46—C511.403 (5)
O2—C131.336 (4)C47—C481.379 (5)
O3—B21.357 (4)C47—H471.0829
O3—H3o0.98 (3)C48—C491.410 (5)
B1—C191.591 (5)C48—H481.0829
B2—C141.549 (5)C49—C501.383 (5)
C1—C21.409 (5)C49—H491.0826
C2—C31.367 (5)C50—C511.405 (5)
C2—H21.0825C50—H501.0831
C3—C41.418 (5)C52—C531.420 (4)
C3—H31.0818C52—C571.407 (4)
C4—C51.371 (5)C53—C541.387 (4)
C4—H41.0835C54—C551.404 (5)
C5—H51.0824C54—H541.0831
C6—C71.355 (5)C55—C561.400 (5)
C6—H61.0841C55—H551.083
C7—C81.442 (5)C56—C571.394 (4)
C8—C91.404 (5)C56—H561.0832
C8—C131.415 (5)C57—H571.0829
C9—C101.376 (5)N7—B71.565 (5)
C9—H91.083N7—C581.356 (4)
C10—C111.394 (5)N7—C641.389 (4)
C10—H101.0821N8—C581.380 (4)
C11—C121.388 (5)N8—C621.351 (5)
C11—H111.0828N8—C631.377 (4)
C12—C131.398 (5)O10—B71.492 (5)
C12—H121.0837O10—B81.378 (4)
C14—C151.403 (4)O11—B81.359 (4)
C14—C191.408 (4)O11—H11o0.98 (3)
C15—C161.392 (4)O12—B71.465 (5)
C15—H151.0831O12—C701.347 (4)
C16—C171.394 (5)B7—C721.594 (5)
C16—H161.083B8—C711.542 (5)
C17—C181.403 (5)C58—C591.409 (5)
C17—H171.083C59—C601.370 (5)
C18—C191.379 (4)C59—H591.083
C18—H181.0827C60—C611.431 (5)
N3—C201.393 (4)C60—H601.0826
N3—C241.363 (5)C61—C621.370 (5)
N3—C251.379 (5)C61—H611.0833
N4—B31.574 (5)C62—H621.0827
N4—C201.343 (4)C63—C641.371 (5)
N4—C261.388 (4)C63—H631.0831
O4—B41.365 (4)C64—C651.444 (5)
O4—H4o0.98 (3)C65—C661.401 (5)
O5—B31.456 (5)C65—C701.405 (5)
O5—C321.343 (4)C66—C671.379 (5)
O6—B31.492 (5)C66—H661.0833
O6—B41.381 (4)C67—C681.399 (5)
B3—C341.591 (5)C67—H671.0814
B4—C331.546 (4)C68—C691.387 (5)
C20—C211.404 (5)C68—H681.0828
C21—C221.376 (5)C69—C701.385 (5)
C21—H211.0832C69—H691.0826
C22—C231.422 (5)C71—C721.414 (4)
C22—H221.0818C71—C761.408 (4)
C23—C241.362 (5)C72—C731.386 (4)
C23—H231.0834C73—C741.397 (4)
C24—H241.083C73—H731.0833
C25—C261.361 (5)C74—C751.407 (4)
C25—H251.0823C74—H741.0826
C26—C271.440 (5)C75—C761.380 (4)
C27—C281.400 (5)C75—H751.0827
C27—C321.408 (5)C76—H761.0833
C28—C291.373 (5)O13—C771.208 (4)
C28—H281.0832C77—C781.500 (5)
C29—C301.399 (5)C77—C791.495 (5)
C29—H291.0836C78—H78a1.0761
C30—C311.397 (5)C78—H78b1.078
C30—H301.0823C78—H78c1.076
C31—C321.395 (5)C79—H79a1.0768
C31—H311.0828C79—H79b1.0768
C33—C341.408 (4)C79—H79c1.0779
C33—C381.397 (4)O14—C801.198 (5)
C34—C351.397 (4)C80—C811.477 (5)
C35—C361.404 (4)C80—C821.492 (6)
C35—H351.0833C81—H81a1.0775
C36—C371.394 (5)C81—H81b1.0765
C36—H361.0828C81—H81c1.077
C37—C381.387 (4)C82—H82a1.0776
C37—H371.082C82—H82b1.0758
C38—H381.0828C82—H82c1.0776
N5—C391.372 (4)O15—C831.206 (5)
N5—C431.361 (5)C83—C841.502 (5)
N5—C441.365 (5)C83—C851.505 (5)
N6—B51.576 (5)C84—H84a1.077
N6—C391.349 (4)C84—H84b1.0756
N6—C451.389 (4)C84—H84c1.0774
O7—B51.487 (5)C85—H85a1.0769
O7—B61.370 (4)C85—H85b1.0766
O8—B51.467 (5)C85—H85c1.0767
O8—C511.341 (4)O16—C861.201 (4)
O9—B61.354 (4)C86—C871.496 (5)
O9—H9o0.99 (3)C86—C881.488 (5)
B5—C531.588 (5)C87—H87a1.0765
B6—C521.551 (5)C87—H87b1.077
C39—C401.414 (5)C87—H87c1.0772
C40—C411.374 (5)C88—H88a1.076
C40—H401.0816C88—H88b1.0771
C41—C421.418 (5)C88—H88c1.0771
B1—N1—C1129.2 (3)N5—C43—C42119.2 (3)
B1—N1—C7122.7 (2)N5—C43—H43120.3
C1—N1—C7107.8 (3)C42—C43—H43120.5
C1—N2—C5122.5 (3)N5—C44—C45108.3 (3)
C1—N2—C6108.2 (3)N5—C44—H44125.95
C5—N2—C6129.3 (3)C45—C44—H44125.79
B1—O1—B2110.0 (3)N6—C45—C44107.6 (3)
B1—O2—C13123.7 (3)N6—C45—C46118.3 (3)
B2—O3—H3o112.9 (18)C44—C45—C46134.1 (3)
N1—B1—O1107.5 (3)C45—C46—C47121.6 (3)
N1—B1—O2106.7 (2)C45—C46—C51118.5 (3)
N1—B1—C19114.8 (3)C47—C46—C51119.9 (3)
O1—B1—O2110.3 (2)C46—C47—C48120.6 (3)
O1—B1—C19104.1 (2)C46—C47—H47119.69
O2—B1—C19113.3 (3)C48—C47—H47119.7
O1—B2—O3121.9 (3)C47—C48—C49119.6 (3)
O1—B2—C14110.6 (3)C47—C48—H48120.2
O3—B2—C14127.5 (3)C49—C48—H48120.24
N1—C1—N2108.0 (3)C48—C49—C50120.5 (3)
N1—C1—C2133.1 (3)C48—C49—H49119.74
N2—C1—C2118.9 (3)C50—C49—H49119.73
C1—C2—C3118.7 (3)C49—C50—C51119.9 (3)
C1—C2—H2120.66C49—C50—H50120.06
C3—C2—H2120.68C51—C50—H50120.07
C2—C3—C4121.2 (3)O8—C51—C46122.2 (3)
C2—C3—H3119.41O8—C51—C50118.3 (3)
C4—C3—H3119.39C46—C51—C50119.5 (3)
C3—C4—C5119.4 (3)B6—C52—C53106.3 (3)
C3—C4—H4120.41B6—C52—C57134.1 (3)
C5—C4—H4120.23C53—C52—C57119.5 (3)
N2—C5—C4119.4 (3)B5—C53—C52108.3 (3)
N2—C5—H5120.28B5—C53—C54131.6 (3)
C4—C5—H5120.35C52—C53—C54120.0 (3)
N2—C6—C7106.9 (3)C53—C54—C55120.6 (3)
N2—C6—H6126.56C53—C54—H54119.74
C7—C6—H6126.54C55—C54—H54119.71
N1—C7—C6109.1 (3)C54—C55—C56119.2 (3)
N1—C7—C8118.6 (3)C54—C55—H55120.39
C6—C7—C8132.2 (3)C56—C55—H55120.43
C7—C8—C9122.4 (3)C55—C56—C57121.2 (3)
C7—C8—C13118.7 (3)C55—C56—H56119.39
C9—C8—C13118.9 (3)C57—C56—H56119.38
C8—C9—C10121.1 (3)C52—C57—C56119.4 (3)
C8—C9—H9119.46C52—C57—H57120.27
C10—C9—H9119.4C56—C57—H57120.28
C9—C10—C11119.7 (3)B7—N7—C58128.6 (3)
C9—C10—H10120.2B7—N7—C64122.6 (3)
C11—C10—H10120.13C58—N7—C64107.6 (2)
C10—C11—C12120.7 (3)C58—N8—C62122.3 (3)
C10—C11—H11119.68C58—N8—C63107.9 (3)
C12—C11—H11119.67C62—N8—C63129.8 (3)
C11—C12—C13120.1 (3)B7—O10—B8110.2 (2)
C11—C12—H12119.98B8—O11—H11o117 (2)
C13—C12—H12119.91B7—O12—C70123.9 (3)
O2—C13—C8121.3 (3)N7—B7—O10106.7 (3)
O2—C13—C12119.0 (3)N7—B7—O12106.8 (2)
C8—C13—C12119.5 (3)N7—B7—C72116.0 (3)
B2—C14—C15133.5 (3)O10—B7—O12111.8 (3)
B2—C14—C19106.5 (3)O10—B7—C72104.0 (2)
C15—C14—C19120.0 (3)O12—B7—C72111.5 (3)
C14—C15—C16119.4 (3)O10—B8—O11122.2 (3)
C14—C15—H15120.28O10—B8—C71110.9 (3)
C16—C15—H15120.28O11—B8—C71126.9 (3)
C15—C16—C17120.4 (3)N7—C58—N8108.7 (3)
C15—C16—H16119.78N7—C58—C59131.8 (3)
C17—C16—H16119.79N8—C58—C59119.5 (3)
C16—C17—C18120.0 (3)C58—C59—C60118.6 (3)
C16—C17—H17119.98C58—C59—H59120.71
C18—C17—H17120.03C60—C59—H59120.69
C17—C18—C19120.0 (3)C59—C60—C61120.5 (3)
C17—C18—H18120C59—C60—H60119.8
C19—C18—H18119.96C61—C60—H60119.72
B1—C19—C14108.7 (3)C60—C61—C62119.3 (3)
B1—C19—C18131.1 (3)C60—C61—H61120.45
C14—C19—C18120.1 (3)C62—C61—H61120.24
C20—N3—C24121.9 (3)N8—C62—C61119.8 (3)
C20—N3—C25108.1 (3)N8—C62—H62120.06
C24—N3—C25130.0 (3)C61—C62—H62120.14
B3—N4—C20129.9 (3)N8—C63—C64107.6 (3)
B3—N4—C26122.9 (3)N8—C63—H63126.19
C20—N4—C26107.2 (3)C64—C63—H63126.2
B4—O4—H4o114.6 (18)N7—C64—C63108.3 (3)
B3—O5—C32124.0 (3)N7—C64—C65118.6 (3)
B3—O6—B4110.6 (2)C63—C64—C65133.1 (3)
N4—B3—O5106.8 (2)C64—C65—C66121.3 (3)
N4—B3—O6107.2 (3)C64—C65—C70118.5 (3)
N4—B3—C34113.6 (3)C66—C65—C70120.1 (3)
O5—B3—O6111.4 (3)C65—C66—C67119.9 (3)
O5—B3—C34114.3 (3)C65—C66—H66120.08
O6—B3—C34103.4 (2)C67—C66—H66120
O4—B4—O6122.3 (3)C66—C67—C68120.5 (3)
O4—B4—C33127.1 (3)C66—C67—H67119.76
O6—B4—C33110.5 (3)C68—C67—H67119.73
N3—C20—N4108.5 (3)C67—C68—C69119.1 (3)
N3—C20—C21119.3 (3)C67—C68—H68120.4
N4—C20—C21132.2 (3)C69—C68—H68120.47
C20—C21—C22119.0 (3)C68—C69—C70121.6 (3)
C20—C21—H21120.51C68—C69—H69119.18
C22—C21—H21120.53C70—C69—H69119.24
C21—C22—C23120.1 (3)O12—C70—C65122.2 (3)
C21—C22—H22119.98O12—C70—C69118.9 (3)
C23—C22—H22119.94C65—C70—C69118.7 (3)
C22—C23—C24120.3 (3)B8—C71—C72106.3 (3)
C22—C23—H23119.9B8—C71—C76133.8 (3)
C24—C23—H23119.77C72—C71—C76119.9 (3)
N3—C24—C23119.5 (3)B7—C72—C71108.5 (3)
N3—C24—H24120.22B7—C72—C73131.9 (3)
C23—C24—H24120.3C71—C72—C73119.6 (3)
N3—C25—C26106.5 (3)C72—C73—C74120.2 (3)
N3—C25—H25126.7C72—C73—H73119.93
C26—C25—H25126.79C74—C73—H73119.88
N4—C26—C25109.7 (3)C73—C74—C75120.3 (3)
N4—C26—C27118.9 (3)C73—C74—H74119.84
C25—C26—C27131.3 (3)C75—C74—H74119.82
C26—C27—C28122.5 (3)C74—C75—C76119.9 (3)
C26—C27—C32118.4 (3)C74—C75—H75120.08
C28—C27—C32119.1 (3)C76—C75—H75120.06
C27—C28—C29121.4 (3)C71—C76—C75120.1 (3)
C27—C28—H28119.28C71—C76—H76119.92
C29—C28—H28119.35C75—C76—H76119.95
C28—C29—C30119.9 (3)O13—C77—C78122.1 (3)
C28—C29—H29120.03O13—C77—C79122.4 (3)
C30—C29—H29120.07C78—C77—C79115.4 (3)
C29—C30—C31119.6 (3)C77—C78—H78a109.43
C29—C30—H30120.23C77—C78—H78b109.38
C31—C30—H30120.17C77—C78—H78c109.48
C30—C31—C32120.6 (3)H78a—C78—H78b109.46
C30—C31—H31119.73H78a—C78—H78c109.61
C32—C31—H31119.66H78b—C78—H78c109.46
O5—C32—C27121.7 (3)C77—C79—H79a109.52
O5—C32—C31118.7 (3)C77—C79—H79b109.51
C27—C32—C31119.4 (3)C77—C79—H79c109.46
B4—C33—C34106.0 (3)H79a—C79—H79b109.5
B4—C33—C38133.6 (3)H79a—C79—H79c109.41
C34—C33—C38120.4 (3)H79b—C79—H79c109.42
B3—C34—C33109.4 (3)O14—C80—C81121.9 (4)
B3—C34—C35131.6 (3)O14—C80—C82122.3 (3)
C33—C34—C35119.1 (3)C81—C80—C82115.8 (3)
C34—C35—C36120.1 (3)C80—C81—H81a109.42
C34—C35—H35119.94C80—C81—H81b109.51
C36—C35—H35119.92C80—C81—H81c109.48
C35—C36—C37120.2 (3)H81a—C81—H81b109.47
C35—C36—H36119.91H81a—C81—H81c109.43
C37—C36—H36119.87H81b—C81—H81c109.51
C36—C37—C38120.0 (3)C80—C82—H82a109.43
C36—C37—H37120.01C80—C82—H82b109.56
C38—C37—H37119.99C80—C82—H82c109.42
C33—C38—C37120.2 (3)H82a—C82—H82b109.51
C33—C38—H38119.91H82a—C82—H82c109.38
C37—C38—H38119.89H82b—C82—H82c109.52
C39—N5—C43122.3 (3)O15—C83—C84120.6 (3)
C39—N5—C44107.8 (3)O15—C83—C85122.7 (3)
C43—N5—C44129.9 (3)C84—C83—C85116.7 (3)
B5—N6—C39127.9 (3)C83—C84—H84a109.38
B5—N6—C45124.0 (3)C83—C84—H84b109.53
C39—N6—C45107.7 (3)C83—C84—H84c109.36
B5—O7—B6110.7 (3)H84a—C84—H84b109.57
B5—O8—C51124.7 (3)H84a—C84—H84c109.44
B6—O9—H9o111.2 (18)H84b—C84—H84c109.55
N6—B5—O7107.2 (3)C83—C85—H85a109.42
N6—B5—O8106.3 (2)C83—C85—H85b109.46
N6—B5—C53114.5 (3)C83—C85—H85c109.41
O7—B5—O8111.0 (3)H85a—C85—H85b109.51
O7—B5—C53104.3 (3)H85a—C85—H85c109.5
O8—B5—C53113.4 (3)H85b—C85—H85c109.53
O7—B6—O9122.4 (3)O16—C86—C87122.1 (3)
O7—B6—C52110.4 (3)O16—C86—C88121.8 (3)
O9—B6—C52127.1 (3)C87—C86—C88116.1 (3)
N5—C39—N6108.6 (3)C86—C87—H87a109.49
N5—C39—C40119.7 (3)C86—C87—H87b109.46
N6—C39—C40131.7 (3)C86—C87—H87c109.42
C39—C40—C41118.3 (3)H87a—C87—H87b109.51
C39—C40—H40120.83H87a—C87—H87c109.5
C41—C40—H40120.9H87b—C87—H87c109.46
C40—C41—C42120.4 (3)C86—C88—H88a109.47
C40—C41—H41119.73C86—C88—H88b109.42
C42—C41—H41119.84C86—C88—H88c109.4
C41—C42—C43120.1 (3)H88a—C88—H88b109.54
C41—C42—H42120.02H88a—C88—H88c109.54
C43—C42—H42119.89H88b—C88—H88c109.45
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O5i1.082.283.353 (4)170.17
C6—H6···O9ii1.082.333.205 (4)136.95
O3—H3o···O60.98 (3)1.71 (3)2.685 (3)174 (3)
C22—H22···O2iii1.082.383.446 (4)169.89
C24—H24···O11iii1.082.443.310 (4)136.15
C25—H25···O11iii1.082.383.207 (4)132.22
C30—H30···O161.082.503.465 (4)148.35
C36—H36···O13iv1.082.423.365 (4)145.23
O4—H4o···O10.98 (3)1.72 (3)2.701 (3)175 (3)
C41—H41···O12iii1.082.453.509 (4)166.60
C43—H43···O31.082.133.189 (4)164.82
C55—H55···O15iv1.082.443.331 (4)138.86
O9—H9o···O100.99 (3)1.71 (3)2.696 (3)174 (3)
C60—H60···O8i1.082.283.338 (4)166.22
C62—H62···O4v1.082.363.284 (4)141.81
C68—H68···O13vi1.082.503.510 (4)155.16
O11—H11o···O70.98 (3)1.70 (3)2.654 (3)164 (3)
C78—H78b···O4i1.082.383.371 (4)152.05
Symmetry codes: (i) x, y, z1; (ii) x+1, y+1/2, z+1; (iii) x+1, y, z; (iv) x+1, y, z+1; (v) x+1, y1/2, z+1; (vi) x, y1/2, z+1.
(odba-b) top
Crystal data top
2(C20H16B2N2O4)·C3H6OF(000) = 1664
Mr = 798.01Dx = 1.296 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2ycCell parameters from 9873 reflections
a = 21.8035 (16) Åθ = 4.4–77.2°
b = 10.4647 (8) ŵ = 0.73 mm1
c = 19.3032 (14) ÅT = 100 K
β = 111.794 (3)°Plate, colourless
V = 4089.6 (5) Å30.29 × 0.13 × 0.06 mm
Z = 4
Data collection top
Bruker D8 VENTURE
diffractometer
4107 independent reflections
Radiation source: microfocus source3264 reflections with I > 3σ(I)
Multi-layer optics monochromatorRint = 0.052
φ or ω oscillation scansθmax = 77.3°, θmin = 4.4°
Absorption correction: multi-scan
Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015
h = 1526
Tmin = 0.688, Tmax = 0.744k = 1112
17247 measured reflectionsl = 2322
Refinement top
Refinement on F21080 constraints
R[F2 > 2σ(F2)] = 0.060H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 2.59(Δ/σ)max = 0.046
4107 reflectionsΔρmax = 0.33 e Å3
333 parametersΔρmin = 0.43 e Å3
13 restraints
Special details top

Refinement. TAAM refinement done with JANA program Petricek, V.; Dusek, M.; Palatinus, L., Crystallographic Computing System Jana2006: General Features. Z. Kristallogr. 2014, 229, 345

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.74274 (9)0.07530 (17)0.03909 (11)0.0550 (9)
O20.54439 (7)0.60890 (12)0.08611 (7)0.0267 (5)
O30.61182 (7)0.22760 (12)0.02899 (7)0.0232 (5)
O40.54555 (7)0.38757 (12)0.05509 (7)0.0253 (5)
N10.53967 (8)0.15995 (15)0.09284 (8)0.0223 (6)
N20.47974 (9)0.03701 (19)0.13639 (9)0.0349 (7)
C10.49301 (10)0.1621 (2)0.12277 (12)0.0317 (8)
C20.45888 (14)0.2625 (3)0.14070 (17)0.0517 (11)
C30.41441 (15)0.2350 (3)0.17301 (18)0.0684 (14)
C40.40290 (16)0.1062 (4)0.18777 (17)0.0721 (15)
C50.43496 (14)0.0089 (3)0.16868 (14)0.0527 (11)
C60.51884 (11)0.0435 (2)0.11367 (11)0.0286 (7)
C70.55590 (9)0.03331 (18)0.08748 (10)0.0209 (6)
C80.60581 (9)0.00523 (18)0.05668 (10)0.0202 (6)
C90.62680 (10)0.11971 (19)0.05130 (11)0.0255 (7)
C100.67249 (11)0.1443 (2)0.01947 (13)0.0329 (8)
C110.69858 (11)0.0421 (2)0.00820 (13)0.0350 (8)
C120.67910 (11)0.0823 (2)0.00308 (12)0.0289 (8)
C130.63197 (9)0.10695 (17)0.02880 (10)0.0203 (6)
C140.7678 (2)0.0232 (3)0.0722 (3)0.080 (2)
C150.62853 (10)0.44673 (18)0.17352 (10)0.0217 (6)
C160.63876 (9)0.31582 (18)0.16308 (10)0.0207 (6)
C170.69048 (10)0.25151 (19)0.21700 (10)0.0245 (7)
C180.73122 (10)0.3153 (2)0.28114 (11)0.0293 (7)
C190.72064 (11)0.4444 (2)0.29193 (11)0.0288 (7)
C200.66957 (10)0.51095 (19)0.23783 (11)0.0258 (7)
B10.56966 (11)0.4906 (2)0.10248 (12)0.0227 (7)
B20.58504 (11)0.2718 (2)0.08456 (12)0.0216 (7)
H20.4678 (15)0.339 (3)0.1327 (17)0.0621*
H30.3840 (15)0.307 (3)0.1830 (16)0.0821*
H40.3691 (17)0.089 (3)0.2082 (17)0.0865*
H50.4323 (14)0.0922 (6)0.1790 (14)0.0633*
H60.5207 (11)0.1460 (4)0.1209 (12)0.0344*
H90.6089 (10)0.2018 (12)0.0724 (11)0.0306*
H100.6890 (11)0.2416 (8)0.0181 (12)0.0394*
H120.6939 (10)0.1598 (14)0.0306 (11)0.0347*
H14a0.7343 (13)0.084 (3)0.1146 (13)0.0965*
H14b0.8000 (13)0.077 (3)0.0251 (11)0.0965*
H14c0.8005 (13)0.018 (3)0.0963 (17)0.0965*
H170.6986 (11)0.1525 (7)0.2064 (11)0.0294*
H180.7692 (8)0.2647 (17)0.3255 (8)0.0351*
H190.7512 (9)0.4913 (17)0.3432 (6)0.0346*
H200.6572 (11)0.6092 (7)0.2445 (12)0.031*
H210.5115 (10)0.616 (2)0.0351 (6)0.0401*
O50.4620 (3)0.2366 (4)0.2304 (3)0.106 (3)0.5
C210.50.4468 (3)0.250.0466 (15)
C220.4567 (3)0.3476 (4)0.2090 (3)0.047 (2)0.5
C230.4046 (3)0.3821 (5)0.1357 (3)0.052 (2)0.5
H23a0.3717180.302230.1148470.0629*0.5
H23b0.4274440.4056750.0964970.0629*0.5
H23c0.37710.4631430.1427860.0629*0.5
H21a0.4713050.5247510.258510.0559*0.5
H21b0.5291280.4802410.2191880.0559*0.5
H21c0.5321980.4102380.3032440.0559*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0505 (11)0.0451 (10)0.0919 (15)0.0053 (9)0.0525 (11)0.0223 (10)
O20.0329 (8)0.0178 (7)0.0256 (7)0.0016 (6)0.0064 (6)0.0031 (6)
O30.0307 (8)0.0197 (7)0.0224 (7)0.0020 (6)0.0135 (6)0.0005 (5)
O40.0270 (7)0.0211 (7)0.0220 (7)0.0035 (6)0.0026 (6)0.0049 (5)
N10.0228 (8)0.0239 (8)0.0221 (8)0.0045 (7)0.0107 (7)0.0080 (6)
N20.0362 (11)0.0483 (11)0.0282 (9)0.0217 (9)0.0213 (8)0.0171 (8)
C10.0294 (11)0.0371 (12)0.0354 (11)0.0126 (10)0.0199 (9)0.0219 (9)
C20.0391 (14)0.0577 (18)0.0722 (18)0.0196 (13)0.0367 (13)0.0456 (16)
C30.0487 (17)0.089 (2)0.090 (2)0.0361 (17)0.0515 (16)0.066 (2)
C40.0585 (19)0.112 (3)0.072 (2)0.0498 (19)0.0539 (16)0.064 (2)
C50.0560 (16)0.075 (2)0.0448 (14)0.0397 (16)0.0397 (13)0.0316 (14)
C60.0379 (12)0.0289 (11)0.0229 (10)0.0128 (10)0.0158 (9)0.0051 (8)
C70.0213 (9)0.0255 (9)0.0161 (8)0.0034 (8)0.0071 (7)0.0040 (7)
C80.0221 (9)0.0191 (9)0.0193 (9)0.0009 (7)0.0077 (7)0.0011 (7)
C90.0241 (10)0.0203 (10)0.0298 (10)0.0019 (8)0.0074 (8)0.0011 (8)
C100.0281 (11)0.0238 (10)0.0485 (13)0.0022 (9)0.0164 (10)0.0049 (9)
C110.0298 (11)0.0321 (12)0.0503 (13)0.0022 (10)0.0231 (10)0.0114 (10)
C120.0328 (11)0.0263 (11)0.0360 (11)0.0037 (9)0.0226 (9)0.0058 (8)
C130.0230 (9)0.0190 (9)0.0211 (9)0.0014 (8)0.0106 (7)0.0012 (7)
C140.089 (3)0.064 (2)0.135 (3)0.028 (2)0.096 (3)0.039 (2)
C150.0216 (9)0.0217 (10)0.0209 (9)0.0026 (8)0.0069 (8)0.0026 (7)
C160.0213 (9)0.0196 (9)0.0231 (9)0.0003 (8)0.0104 (8)0.0002 (7)
C170.0252 (10)0.0234 (10)0.0229 (10)0.0009 (8)0.0067 (8)0.0006 (8)
C180.0264 (10)0.0301 (11)0.0245 (10)0.0006 (9)0.0016 (8)0.0004 (8)
C190.0296 (11)0.0280 (11)0.0232 (10)0.0037 (9)0.0033 (8)0.0024 (8)
C200.0266 (10)0.0254 (10)0.0222 (10)0.0043 (9)0.0052 (8)0.0045 (8)
B10.0256 (11)0.0206 (11)0.0242 (10)0.0015 (9)0.0119 (9)0.0008 (8)
B20.0224 (11)0.0207 (10)0.0221 (10)0.0017 (9)0.0086 (8)0.0003 (8)
O50.159 (6)0.031 (2)0.086 (4)0.002 (3)0.002 (4)0.003 (2)
C210.050 (2)0.039 (2)0.055 (2)00.0242 (18)0
C220.066 (3)0.026 (2)0.046 (3)0.005 (2)0.019 (3)0.005 (2)
C230.056 (3)0.057 (3)0.045 (3)0.005 (3)0.020 (3)0.019 (3)
Geometric parameters (Å, º) top
O1—C111.352 (3)C8—C131.407 (3)
O1—C141.424 (5)C9—C101.375 (3)
O2—B11.344 (2)C10—C111.407 (3)
O3—C131.337 (2)C11—C121.384 (3)
O4—B11.385 (2)C12—C131.404 (3)
N1—C11.344 (3)C15—C161.414 (3)
N1—C71.385 (3)C15—C201.404 (2)
N1—B21.578 (3)C15—B11.558 (2)
N2—C11.387 (3)C16—C171.392 (2)
N2—C51.371 (3)C16—B21.601 (2)
N2—C61.380 (3)C17—C181.396 (2)
C1—C21.402 (4)C18—C191.399 (3)
C2—C31.365 (5)C19—C201.397 (3)
C2—H20.85 (3)O5—O5i1.545 (8)
C3—C41.419 (5)O5—C221.224 (6)
C4—C51.362 (5)C21—C221.428 (5)
C4—H40.97 (5)C21—C22i1.428 (5)
C6—C71.364 (3)C22—C231.493 (7)
C7—C81.451 (3)C22—H21ci0.7659
C8—C91.401 (3)H21a—H21bi0.6367
C11—O1—C14117.8 (3)O1—C11—C12124.1 (2)
C1—N1—C7107.67 (19)C10—C11—C12120.6 (2)
C1—N1—B2129.28 (19)C11—C12—C13119.9 (2)
C7—N1—B2121.03 (18)O3—C13—C8122.2 (2)
C1—N2—C5121.5 (2)O3—C13—C12118.02 (19)
C1—N2—C6108.6 (2)C8—C13—C12119.69 (19)
C5—N2—C6129.9 (2)C16—C15—C20120.47 (16)
N1—C1—N2108.0 (2)C16—C15—B1106.41 (15)
N1—C1—C2132.4 (2)C20—C15—B1133.08 (19)
N2—C1—C2119.6 (2)C15—C16—C17119.29 (16)
C1—C2—C3119.1 (3)C15—C16—B2108.31 (15)
C1—C2—H2119 (3)C17—C16—B2132.38 (19)
C3—C2—H2122 (3)C16—C17—C18120.23 (19)
C2—C3—C4120.1 (3)C17—C18—C19120.53 (16)
C3—C4—C5120.6 (4)C18—C19—C20120.01 (16)
C3—C4—H4118.3 (19)C15—C20—C19119.45 (19)
C5—C4—H4120.9 (19)O2—B1—O4122.61 (14)
N2—C5—C4119.1 (3)O2—B1—C15127.60 (16)
N2—C6—C7106.20 (19)O4—B1—C15109.78 (16)
N1—C7—C6109.5 (2)N1—B2—C16112.57 (15)
N1—C7—C8118.40 (19)O5i—O5—C2296.6 (5)
C6—C7—C8132.1 (2)C22—C21—C22i86.8 (3)
C7—C8—C9122.3 (2)O5—C22—C21122.9 (4)
C7—C8—C13118.42 (19)O5—C22—C23119.5 (5)
C9—C8—C13119.2 (2)O5—C22—H21ci156.26
C8—C9—C10121.2 (2)C21—C22—C23117.6 (4)
C9—C10—C11119.3 (2)C21—C22—H21ci47.89
O1—C11—C10115.3 (2)C23—C22—H21ci73.56
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O51.083 (8)1.793 (11)2.801 (5)152.9 (14)
C10—H10···O1ii1.084 (11)2.367 (14)3.413 (3)161.7 (13)
C12—H12···C141.089 (18)2.49 (2)2.796 (6)94.3 (9)
O2—H21···O4iii0.979 (12)1.728 (12)2.7032 (17)174.4 (19)
C21—H21c···O5i1.081.952.331 (5)96.50
C21—H21c···C22i1.080.771.428 (5)100.27
C21—H21c···C23i1.081.472.499 (5)156.86
C22i—H21c···C210.771.081.428 (5)100.27
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+3/2, y1/2, z; (iii) x+1, y+1, z.
(odba-d) top
Crystal data top
C19H13B2BrN2O3Z = 4
Mr = 418.8F(000) = 840
Triclinic, P1Dx = 1.551 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9492 (7) ÅCell parameters from 9881 reflections
b = 14.5926 (12) Åθ = 3.3–28.9°
c = 15.0762 (12) ŵ = 2.31 mm1
α = 66.778 (3)°T = 100 K
β = 82.477 (3)°Block, colourless
γ = 86.204 (3)°0.28 × 0.17 × 0.09 mm
V = 1793.5 (3) Å3
Data collection top
Bruker D8 VENTURE
diffractometer
12047 independent reflections
Radiation source: sealed-tube7212 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.054
φ or ω oscillation scansθmax = 32.7°, θmin = 3.0°
Absorption correction: multi-scan
Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015
h = 1313
Tmin = 0.682, Tmax = 0.746k = 2121
72753 measured reflectionsl = 2122
Refinement top
Refinement on F21689 constraints
R[F2 > 2σ(F2)] = 0.048All H-atom parameters refined
wR(F2) = 0.102Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.97(Δ/σ)max = 0.019
12047 reflectionsΔρmax = 3.73 e Å3
566 parametersΔρmin = 0.79 e Å3
26 restraints
Special details top

Refinement. TAAM refinement done with JANA program Petricek, V.; Dusek, M.; Palatinus, L., Crystallographic Computing System Jana2006: General Features. Z. Kristallogr. 2014, 229, 345

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.72056 (3)0.60623 (2)0.181589 (19)0.02767 (11)
O10.29092 (17)0.03593 (12)0.52095 (11)0.0157 (6)
O20.43056 (16)0.09949 (11)0.51705 (11)0.0144 (6)
O30.50466 (17)0.26646 (12)0.42160 (11)0.0180 (6)
B10.2966 (3)0.0570 (2)0.51839 (18)0.0131 (9)
B20.4074 (3)0.2040 (2)0.50760 (19)0.0151 (10)
N10.4637 (2)0.21537 (14)0.59749 (13)0.0144 (7)
N20.4966 (2)0.19935 (15)0.74527 (14)0.0183 (8)
C10.4300 (3)0.15803 (18)0.69256 (17)0.0159 (9)
C20.3424 (3)0.07184 (19)0.74038 (18)0.0209 (9)
C30.3281 (3)0.03025 (19)0.83981 (18)0.0238 (10)
C40.3993 (3)0.0733 (2)0.89218 (18)0.0257 (10)
C50.4819 (3)0.1570 (2)0.84486 (18)0.0251 (10)
C60.5712 (3)0.28423 (18)0.68149 (18)0.0191 (9)
C70.5491 (3)0.29390 (17)0.59076 (17)0.0155 (9)
C80.5945 (2)0.36898 (17)0.49466 (17)0.0158 (9)
C90.6620 (3)0.45883 (18)0.48029 (18)0.0184 (9)
C100.7036 (3)0.52888 (19)0.38814 (19)0.0207 (9)
C110.6741 (3)0.50881 (18)0.30865 (17)0.0193 (9)
C120.6083 (3)0.42172 (19)0.31880 (18)0.0191 (9)
C130.5665 (2)0.35069 (18)0.41361 (17)0.0160 (9)
C140.2291 (3)0.22189 (17)0.50571 (16)0.0144 (8)
C150.1634 (2)0.13282 (17)0.51499 (16)0.0147 (8)
C160.0075 (3)0.12682 (19)0.51715 (17)0.0187 (9)
C170.0835 (3)0.2104 (2)0.50891 (19)0.0218 (10)
C180.0189 (3)0.2996 (2)0.49794 (19)0.0233 (10)
C190.1359 (3)0.30518 (18)0.49656 (17)0.0188 (9)
H1o0.3910 (13)0.0647 (18)0.5108 (19)0.014 (7)*
H20.297 (3)0.0444 (18)0.6925 (15)0.0251*
H30.258 (2)0.0351 (12)0.8722 (17)0.0285*
H40.382 (3)0.0497 (19)0.9704 (3)0.0308*
H50.530 (3)0.1992 (17)0.8792 (17)0.0302*
H60.633 (2)0.3298 (16)0.7056 (17)0.0229*
H90.675 (3)0.4769 (18)0.5419 (11)0.022*
H100.752 (3)0.5995 (9)0.3762 (18)0.0249*
H120.590 (3)0.4076 (19)0.2558 (11)0.023*
H160.046 (3)0.0585 (10)0.5267 (18)0.0225*
H170.2040 (6)0.2075 (19)0.5088 (18)0.0261*
H180.082 (2)0.3682 (10)0.4876 (18)0.028*
H190.184 (3)0.3736 (10)0.4914 (18)0.0225*
Br20.05274 (3)0.02847 (2)1.19386 (2)0.03556 (13)
O40.57948 (18)0.39765 (12)0.98467 (11)0.0187 (6)
O50.57061 (19)0.56489 (13)0.86603 (11)0.0207 (7)
O60.53723 (19)0.22455 (13)1.01301 (11)0.0221 (7)
B30.6188 (3)0.4688 (2)0.89453 (19)0.0180 (10)
B40.6508 (3)0.2996 (2)0.99513 (19)0.0194 (10)
N30.7316 (2)0.26363 (15)1.09036 (13)0.0175 (7)
N40.8717 (2)0.25682 (16)1.20356 (14)0.0214 (8)
C200.8641 (3)0.29243 (18)1.10489 (17)0.0196 (9)
C210.9840 (3)0.3482 (2)1.04002 (18)0.0255 (10)
C221.1066 (3)0.3642 (2)1.0781 (2)0.0282 (11)
C231.1118 (3)0.3258 (2)1.17989 (19)0.0284 (11)
C240.9947 (3)0.2724 (2)1.24092 (18)0.0254 (10)
C250.7411 (3)0.20622 (19)1.25110 (17)0.0215 (9)
C260.6545 (3)0.21151 (18)1.18055 (16)0.0184 (9)
C270.5082 (3)0.17192 (18)1.18682 (17)0.0196 (9)
C280.4222 (3)0.1206 (2)1.27462 (18)0.0260 (10)
C290.2861 (3)0.0768 (2)1.27880 (19)0.0294 (11)
C300.2373 (3)0.0870 (2)1.19143 (19)0.0249 (10)
C310.3169 (3)0.13956 (19)1.10202 (18)0.0222 (10)
C320.4552 (3)0.18086 (18)1.09940 (17)0.0189 (9)
C330.7538 (3)0.32250 (18)0.89358 (17)0.0189 (9)
C340.7302 (3)0.42263 (19)0.83309 (16)0.0186 (9)
C350.8027 (3)0.4626 (2)0.73856 (17)0.0214 (10)
C360.8994 (3)0.4013 (2)0.70402 (19)0.0276 (11)
C370.9228 (3)0.3024 (2)0.7628 (2)0.0274 (11)
C380.8509 (3)0.2619 (2)0.85778 (19)0.0249 (10)
H210.973 (3)0.3798 (18)0.9630 (5)0.0306*
H221.198 (2)0.4066 (17)1.0275 (15)0.0338*
H231.2101 (18)0.337 (2)1.2091 (18)0.0341*
H240.977 (3)0.2404 (18)1.3196 (2)0.0305*
H280.462 (3)0.114 (2)1.3420 (10)0.0313*
H290.221 (3)0.0267 (16)1.3436 (11)0.0353*
H310.263 (3)0.1440 (19)1.0401 (11)0.0266*
H350.777 (3)0.5393 (6)0.6936 (15)0.0256*
H360.953 (3)0.4371 (18)0.6304 (7)0.0331*
H370.994 (2)0.2517 (16)0.7389 (19)0.0329*
H380.880 (3)0.1857 (7)0.9023 (16)0.0299*
H200.505 (3)0.579 (2)0.9171 (16)0.031*
H5o0.716 (3)0.1764 (18)1.3294 (3)0.0259*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03108 (16)0.02376 (15)0.02174 (14)0.00886 (12)0.00000 (11)0.00167 (11)
O10.0135 (8)0.0173 (9)0.0181 (8)0.0007 (7)0.0029 (7)0.0083 (7)
O20.0114 (8)0.0174 (9)0.0170 (8)0.0004 (6)0.0018 (6)0.0093 (7)
O30.0184 (9)0.0211 (9)0.0171 (8)0.0044 (7)0.0006 (7)0.0103 (7)
B10.0187 (13)0.0153 (14)0.0062 (12)0.0007 (11)0.0005 (10)0.0053 (10)
B20.0151 (13)0.0187 (14)0.0139 (13)0.0001 (11)0.0031 (10)0.0084 (11)
N10.0128 (10)0.0157 (10)0.0168 (10)0.0010 (8)0.0019 (8)0.0084 (8)
N20.0221 (11)0.0183 (11)0.0184 (10)0.0004 (9)0.0079 (8)0.0096 (9)
C10.0173 (12)0.0166 (12)0.0169 (12)0.0021 (10)0.0052 (9)0.0084 (10)
C20.0264 (14)0.0203 (13)0.0163 (13)0.0074 (11)0.0021 (10)0.0065 (11)
C30.0296 (14)0.0217 (14)0.0190 (13)0.0015 (11)0.0014 (11)0.0070 (11)
C40.0360 (16)0.0257 (15)0.0164 (13)0.0000 (12)0.0061 (11)0.0085 (12)
C50.0369 (16)0.0242 (15)0.0175 (13)0.0022 (12)0.0103 (11)0.0090 (11)
C60.0223 (13)0.0195 (13)0.0207 (13)0.0015 (10)0.0082 (10)0.0115 (11)
C70.0127 (11)0.0142 (12)0.0198 (12)0.0014 (9)0.0019 (9)0.0070 (10)
C80.0148 (11)0.0146 (12)0.0198 (12)0.0014 (9)0.0036 (9)0.0078 (10)
C90.0185 (12)0.0152 (13)0.0237 (13)0.0026 (10)0.0040 (10)0.0092 (11)
C100.0201 (13)0.0161 (13)0.0247 (14)0.0033 (10)0.0029 (10)0.0059 (11)
C110.0150 (12)0.0184 (13)0.0214 (13)0.0030 (10)0.0002 (10)0.0048 (10)
C120.0180 (12)0.0201 (13)0.0178 (13)0.0037 (10)0.0003 (10)0.0058 (11)
C130.0140 (11)0.0176 (12)0.0165 (12)0.0014 (9)0.0013 (9)0.0069 (10)
C140.0157 (12)0.0151 (12)0.0136 (11)0.0018 (9)0.0019 (9)0.0066 (9)
C150.0128 (11)0.0166 (12)0.0146 (11)0.0013 (9)0.0042 (9)0.0052 (10)
C160.0124 (12)0.0225 (14)0.0235 (13)0.0018 (10)0.0012 (10)0.0114 (11)
C170.0128 (12)0.0240 (14)0.0332 (14)0.0047 (11)0.0048 (11)0.0162 (12)
C180.0164 (13)0.0248 (15)0.0321 (14)0.0058 (11)0.0053 (11)0.0148 (12)
C190.0197 (13)0.0159 (13)0.0232 (13)0.0016 (10)0.0052 (10)0.0097 (11)
Br20.02619 (16)0.0470 (2)0.03340 (17)0.01478 (13)0.00007 (12)0.01435 (15)
O40.0237 (9)0.0206 (9)0.0098 (8)0.0033 (7)0.0002 (7)0.0040 (7)
O50.0243 (10)0.0216 (10)0.0138 (9)0.0021 (8)0.0015 (7)0.0044 (7)
O60.0296 (10)0.0273 (10)0.0113 (8)0.0077 (8)0.0002 (7)0.0089 (7)
B30.0173 (14)0.0233 (16)0.0160 (13)0.0040 (12)0.0062 (11)0.0084 (12)
B40.0221 (15)0.0255 (16)0.0121 (13)0.0036 (12)0.0014 (11)0.0086 (12)
N30.0219 (11)0.0168 (11)0.0129 (10)0.0015 (8)0.0001 (8)0.0052 (8)
N40.0289 (12)0.0231 (12)0.0122 (10)0.0030 (9)0.0029 (9)0.0062 (9)
C200.0256 (14)0.0201 (13)0.0117 (12)0.0048 (11)0.0007 (10)0.0045 (10)
C210.0287 (15)0.0292 (15)0.0158 (13)0.0102 (12)0.0006 (11)0.0049 (11)
C220.0288 (15)0.0333 (16)0.0230 (14)0.0121 (12)0.0032 (11)0.0096 (12)
C230.0308 (15)0.0345 (16)0.0211 (14)0.0087 (13)0.0068 (12)0.0097 (12)
C240.0301 (15)0.0298 (15)0.0162 (13)0.0058 (12)0.0052 (11)0.0072 (12)
C250.0280 (14)0.0268 (14)0.0080 (11)0.0035 (11)0.0016 (10)0.0045 (11)
C260.0218 (13)0.0165 (13)0.0167 (12)0.0016 (10)0.0008 (10)0.0069 (10)
C270.0253 (13)0.0209 (13)0.0114 (12)0.0006 (10)0.0011 (10)0.0053 (10)
C280.0241 (14)0.0360 (16)0.0136 (13)0.0055 (12)0.0004 (11)0.0049 (12)
C290.0258 (15)0.0400 (17)0.0180 (14)0.0094 (12)0.0006 (11)0.0057 (12)
C300.0247 (14)0.0287 (15)0.0207 (14)0.0046 (12)0.0009 (11)0.0094 (12)
C310.0244 (14)0.0237 (14)0.0190 (13)0.0044 (11)0.0012 (11)0.0088 (11)
C320.0216 (13)0.0193 (13)0.0156 (12)0.0021 (10)0.0001 (10)0.0071 (10)
C330.0229 (13)0.0216 (14)0.0144 (12)0.0033 (11)0.0015 (10)0.0090 (11)
C340.0220 (13)0.0231 (14)0.0101 (11)0.0069 (10)0.0018 (9)0.0049 (10)
C350.0212 (13)0.0278 (15)0.0140 (12)0.0042 (11)0.0029 (10)0.0080 (11)
C360.0259 (14)0.0404 (18)0.0175 (13)0.0074 (13)0.0026 (11)0.0129 (13)
C370.0237 (14)0.0390 (18)0.0237 (14)0.0008 (12)0.0012 (11)0.0182 (13)
C380.0275 (14)0.0305 (16)0.0188 (14)0.0014 (12)0.0020 (11)0.0124 (12)
Geometric parameters (Å, º) top
Br1—C111.894 (2)Br2—C301.899 (3)
O1—B11.345 (4)O4—B31.364 (3)
O2—B11.381 (3)O5—B31.353 (3)
O3—C131.336 (3)O6—C321.341 (3)
B1—C151.563 (4)B3—C341.571 (4)
B2—N11.577 (4)B4—N31.578 (3)
B2—C141.602 (4)B4—C331.603 (4)
N1—C11.350 (3)N3—C201.355 (4)
N1—C71.382 (4)N3—C261.383 (3)
N2—C11.379 (4)N4—C201.379 (3)
N2—C51.372 (3)N4—C241.370 (4)
N2—C61.380 (3)N4—C251.379 (3)
C1—C21.409 (4)C20—C211.409 (3)
C2—C31.369 (4)C21—C221.376 (4)
C3—C41.414 (5)C22—C231.417 (4)
C4—C51.357 (4)C23—C241.357 (3)
C6—C71.358 (5)C25—C261.371 (4)
C7—C81.455 (3)C26—C271.443 (4)
C8—C91.405 (4)C27—C281.390 (3)
C8—C131.406 (5)C27—C321.413 (5)
C9—C101.382 (3)C28—C291.395 (4)
C10—C111.399 (5)C29—C301.392 (5)
C11—C121.381 (4)C30—C311.385 (3)
C12—C131.414 (3)C31—C321.401 (4)
C14—C151.411 (4)C33—C341.403 (3)
C14—C191.399 (4)C33—C381.407 (4)
C15—C161.399 (3)C34—C351.394 (4)
C16—C171.394 (4)C35—C361.403 (4)
C17—C181.400 (4)C36—C371.383 (3)
C18—C191.390 (4)C37—C381.399 (4)
O1—B1—O2122.1 (2)O4—B3—O5123.6 (2)
O1—B1—C15128.1 (2)O4—B3—C34109.8 (2)
O2—B1—C15109.8 (2)O5—B3—C34126.6 (2)
N1—B2—C14112.2 (2)N3—B4—C33118.0 (2)
B2—N1—C1127.9 (2)B4—N3—C20129.71 (16)
B2—N1—C7124.03 (17)B4—N3—C26121.1 (2)
C1—N1—C7107.8 (2)C20—N3—C26107.6 (2)
C1—N2—C5121.15 (19)C20—N4—C24121.8 (2)
C1—N2—C6108.7 (2)C20—N4—C25108.6 (2)
C5—N2—C6130.2 (2)C24—N4—C25129.66 (19)
N1—C1—N2107.8 (2)N3—C20—N4108.20 (19)
N1—C1—C2131.8 (3)N3—C20—C21132.2 (3)
N2—C1—C2120.4 (2)N4—C20—C21119.6 (3)
C1—C2—C3117.9 (3)C20—C21—C22118.2 (3)
C2—C3—C4120.6 (2)C21—C22—C23120.9 (2)
C3—C4—C5120.6 (3)C22—C23—C24119.8 (3)
N2—C5—C4119.3 (3)N4—C24—C23119.7 (3)
N2—C6—C7106.5 (3)N4—C25—C26106.6 (2)
N1—C7—C6109.2 (2)N3—C26—C25109.0 (2)
N1—C7—C8118.2 (3)N3—C26—C27119.5 (3)
C6—C7—C8132.6 (3)C25—C26—C27131.5 (2)
C7—C8—C9122.8 (3)C26—C27—C28123.0 (3)
C7—C8—C13117.9 (3)C26—C27—C32117.9 (2)
C9—C8—C13119.3 (2)C28—C27—C32119.0 (3)
C8—C9—C10121.5 (3)C27—C28—C29121.8 (3)
C9—C10—C11118.0 (3)C28—C29—C30117.7 (2)
Br1—C11—C10119.0 (2)Br2—C30—C29119.04 (18)
Br1—C11—C12118.1 (2)Br2—C30—C31118.3 (2)
C10—C11—C12122.9 (2)C29—C30—C31122.7 (3)
C11—C12—C13118.4 (3)C30—C31—C32118.8 (3)
O3—C13—C8122.7 (2)O6—C32—C27121.6 (2)
O3—C13—C12117.4 (3)O6—C32—C31118.3 (3)
C8—C13—C12119.9 (3)C27—C32—C31120.0 (2)
B2—C14—C15108.7 (2)B4—C33—C34108.2 (2)
B2—C14—C19132.5 (3)B4—C33—C38132.3 (2)
C15—C14—C19118.8 (2)C34—C33—C38119.4 (2)
B1—C15—C14106.20 (19)B3—C34—C33106.6 (2)
B1—C15—C16132.9 (3)B3—C34—C35132.6 (2)
C14—C15—C16120.8 (2)C33—C34—C35120.8 (3)
C15—C16—C17119.4 (3)C34—C35—C36119.2 (2)
C16—C17—C18120.1 (3)C35—C36—C37120.5 (2)
C17—C18—C19120.4 (3)C36—C37—C38120.6 (3)
C14—C19—C18120.4 (3)C33—C38—C37119.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.985 (16)1.693 (15)2.672 (2)172 (2)
C5—H5···O61.08 (4)2.20 (3)3.163 (4)146.7 (18)
C12—H12···O5ii1.08 (2)2.38 (2)3.326 (4)146 (2)
C16—H16···O1iii1.08 (2)2.48 (3)3.270 (4)129.5 (15)
C23—H23···O5iv1.08 (3)2.39 (2)3.212 (3)132.0 (18)
O5—H20···O4v0.98 (3)1.72 (3)2.692 (2)169 (3)
C25—H5o···O1vi1.082 (6)2.370 (15)3.343 (3)149 (2)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x, y, z+1; (iv) x+2, y+1, z+2; (v) x+1, y+1, z+2; (vi) x+1, y, z+2.
 

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