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
CCDC references: 1846570; 1846571; 1846572; 1846573; 1846574
Crystal data top
C14H12N2O2 | F(000) = 1008 |
Mr = 240.3 | Dx = 1.412 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 9422 reflections |
a = 14.5448 (2) Å | θ = 3.7–76.9° |
b = 6.5214 (4) Å | µ = 0.79 mm−1 |
c = 23.8246 (6) Å | T = 100 K |
V = 2259.82 (15) Å3 | Block, colourless |
Z = 8 | 0.20 × 0.14 × 0.11 mm |
Data collection top
Bruker D8 VENTURE diffractometer | 2331 independent reflections |
Radiation source: microfocus source | 1831 reflections with I > 3σ(I) |
Multi-layer optics monochromator | Rint = 0.042 |
φ or ω oscillation scans | θmax = 77.4°, θmin = 3.7° |
Absorption correction: multi-scan Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015 | h = −16→18 |
Tmin = 0.690, Tmax = 0.754 | k = −7→8 |
18355 measured reflections | l = −30→20 |
Refinement top
Refinement on F2 | 600 constraints |
R[F2 > 2σ(F2)] = 0.033 | All H-atom parameters refined |
wR(F2) = 0.075 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
S = 1.70 | (Δ/σ)max = 0.015 |
2331 reflections | Δρmax = 0.25 e Å−3 |
199 parameters | Δρmin = −0.32 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.04817 (7) | 0.30245 (14) | 0.10446 (4) | 0.0191 (3) | |
O2 | 0.12775 (7) | 0.28056 (14) | −0.09012 (4) | 0.0197 (3) | |
N1 | 0.10048 (7) | 0.61288 (17) | 0.16520 (4) | 0.0164 (3) | |
N2 | 0.14932 (7) | 0.93075 (16) | 0.18284 (4) | 0.0160 (3) | |
C1 | 0.11032 (8) | 0.7527 (2) | 0.20507 (6) | 0.0167 (4) | |
C2 | 0.09013 (9) | 0.7473 (2) | 0.26316 (6) | 0.0211 (4) | |
C3 | 0.11129 (9) | 0.9131 (2) | 0.29580 (6) | 0.0224 (4) | |
C4 | 0.15087 (10) | 1.0921 (2) | 0.27128 (6) | 0.0224 (4) | |
C5 | 0.16851 (9) | 1.0995 (2) | 0.21510 (6) | 0.0202 (4) | |
C6 | 0.16468 (9) | 0.8963 (2) | 0.12662 (5) | 0.0157 (4) | |
C7 | 0.13363 (9) | 0.69904 (19) | 0.11647 (5) | 0.0143 (4) | |
C8 | 0.13111 (8) | 0.58662 (19) | 0.06352 (5) | 0.0137 (4) | |
C9 | 0.17093 (9) | 0.66836 (19) | 0.01462 (6) | 0.0154 (4) | |
C10 | 0.16879 (9) | 0.5650 (2) | −0.03598 (5) | 0.0158 (4) | |
C11 | 0.12562 (9) | 0.37264 (19) | −0.03903 (5) | 0.0152 (4) | |
C12 | 0.08560 (9) | 0.2877 (2) | 0.00845 (5) | 0.0152 (4) | |
C13 | 0.08811 (8) | 0.3931 (2) | 0.05965 (5) | 0.0148 (4) | |
C14 | 0.08758 (11) | 0.0821 (2) | −0.09476 (6) | 0.0230 (4) | |
H2 | 0.0578 (9) | 0.6088 (12) | 0.2786 (6) | 0.0253* | |
H3 | 0.0983 (10) | 0.913 (2) | 0.34054 (14) | 0.0269* | |
H4 | 0.1692 (9) | 1.2211 (14) | 0.2976 (5) | 0.0269* | |
H5 | 0.1954 (9) | 1.2334 (13) | 0.1938 (5) | 0.0242* | |
H6 | 0.1945 (8) | 1.0110 (15) | 0.0993 (4) | 0.0188* | |
H9 | 0.2060 (8) | 0.8147 (10) | 0.0166 (6) | 0.0185* | |
H10 | 0.2018 (8) | 0.627 (2) | −0.0730 (3) | 0.0189* | |
H12 | 0.0532 (8) | 0.1383 (9) | 0.0075 (5) | 0.0182* | |
H14a | 0.1024 (9) | 0.035 (2) | −0.1371 (2) | 0.0276* | |
H14b | 0.1219 (9) | −0.0249 (18) | −0.0674 (5) | 0.0276* | |
H14c | 0.0148 (2) | 0.085 (2) | −0.0867 (6) | 0.0276* | |
H15 | 0.0603 (12) | 0.395 (2) | 0.1366 (5) | 0.0286* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0229 (5) | 0.0157 (5) | 0.0186 (5) | −0.0042 (4) | 0.0044 (4) | 0.0019 (4) |
O2 | 0.0247 (5) | 0.0184 (5) | 0.0161 (5) | −0.0009 (4) | −0.0015 (4) | 0.0009 (4) |
N1 | 0.0187 (6) | 0.0157 (6) | 0.0148 (5) | −0.0019 (4) | 0.0019 (4) | 0.0017 (4) |
N2 | 0.0146 (5) | 0.0156 (5) | 0.0177 (6) | −0.0003 (4) | 0.0002 (4) | −0.0005 (4) |
C1 | 0.0160 (6) | 0.0181 (7) | 0.0159 (7) | −0.0016 (5) | 0.0022 (5) | 0.0012 (5) |
C2 | 0.0204 (7) | 0.0278 (8) | 0.0151 (7) | −0.0016 (6) | 0.0028 (6) | −0.0008 (6) |
C3 | 0.0208 (7) | 0.0299 (8) | 0.0166 (7) | −0.0009 (6) | 0.0016 (6) | −0.0027 (6) |
C4 | 0.0212 (7) | 0.0259 (8) | 0.0202 (7) | −0.0024 (6) | 0.0007 (6) | −0.0063 (6) |
C5 | 0.0208 (7) | 0.0191 (7) | 0.0207 (7) | −0.0035 (6) | 0.0020 (5) | −0.0037 (6) |
C6 | 0.0165 (6) | 0.0140 (7) | 0.0165 (6) | −0.0028 (5) | 0.0008 (5) | 0.0019 (5) |
C7 | 0.0149 (6) | 0.0138 (6) | 0.0142 (6) | 0.0001 (5) | 0.0010 (5) | 0.0013 (5) |
C8 | 0.0137 (6) | 0.0122 (6) | 0.0152 (6) | −0.0017 (5) | 0.0000 (5) | 0.0020 (5) |
C9 | 0.0169 (6) | 0.0145 (6) | 0.0149 (6) | −0.0027 (5) | 0.0007 (5) | 0.0018 (5) |
C10 | 0.0175 (6) | 0.0152 (6) | 0.0146 (6) | −0.0008 (5) | 0.0004 (5) | 0.0013 (5) |
C11 | 0.0163 (6) | 0.0145 (6) | 0.0147 (6) | 0.0003 (5) | −0.0009 (5) | 0.0006 (5) |
C12 | 0.0173 (6) | 0.0134 (6) | 0.0149 (7) | −0.0018 (5) | 0.0005 (5) | 0.0015 (5) |
C13 | 0.0152 (6) | 0.0138 (6) | 0.0155 (6) | −0.0005 (5) | 0.0002 (5) | 0.0011 (5) |
C14 | 0.0306 (8) | 0.0201 (7) | 0.0183 (7) | −0.0021 (6) | −0.0024 (6) | −0.0015 (6) |
Geometric parameters (Å, º) top
O1—C13 | 1.3514 (15) | C3—C4 | 1.4268 (19) |
O2—C11 | 1.3574 (15) | C4—C5 | 1.364 (2) |
O2—C14 | 1.4244 (15) | C6—C7 | 1.3849 (18) |
N1—C1 | 1.3244 (18) | C7—C8 | 1.4593 (17) |
N1—C7 | 1.3768 (16) | C8—C9 | 1.4064 (18) |
N2—C1 | 1.3964 (18) | C8—C13 | 1.4114 (18) |
N2—C5 | 1.3713 (18) | C9—C10 | 1.3816 (19) |
N2—C6 | 1.3763 (15) | C10—C11 | 1.4049 (19) |
C1—C2 | 1.415 (2) | C11—C12 | 1.3874 (17) |
C2—C3 | 1.3669 (19) | C12—C13 | 1.4006 (17) |
| | | |
C11—O2—C14 | 117.51 (10) | N1—C7—C8 | 121.01 (12) |
C1—N1—C7 | 106.63 (12) | C6—C7—C8 | 128.74 (11) |
C1—N2—C5 | 122.51 (11) | C7—C8—C9 | 121.02 (12) |
C1—N2—C6 | 107.43 (11) | C7—C8—C13 | 121.12 (11) |
C5—N2—C6 | 130.04 (12) | C9—C8—C13 | 117.86 (11) |
N1—C1—N2 | 110.13 (12) | C8—C9—C10 | 121.91 (12) |
N1—C1—C2 | 131.44 (12) | C9—C10—C11 | 119.41 (11) |
N2—C1—C2 | 118.42 (12) | O2—C11—C10 | 115.53 (11) |
C1—C2—C3 | 119.34 (12) | O2—C11—C12 | 124.35 (11) |
C2—C3—C4 | 120.34 (13) | C10—C11—C12 | 120.11 (11) |
C3—C4—C5 | 120.44 (12) | C11—C12—C13 | 120.22 (12) |
N2—C5—C4 | 118.92 (12) | O1—C13—C8 | 121.98 (11) |
N2—C6—C7 | 105.57 (11) | O1—C13—C12 | 117.53 (11) |
N1—C7—C6 | 110.23 (11) | C8—C13—C12 | 120.49 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H15···N1 | 0.990 (12) | 1.682 (13) | 2.6020 (14) | 152.7 (11) |
O1—H15···C7 | 0.990 (12) | 2.304 (13) | 2.8832 (15) | 116.4 (9) |
Crystal data top
C13H9BrN2O | F(000) = 576 |
Mr = 289.1 | Dx = 1.747 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9928 reflections |
a = 12.8423 (7) Å | θ = 3.3–30.5° |
b = 7.0971 (4) Å | µ = 3.72 mm−1 |
c = 12.6239 (7) Å | T = 100 K |
β = 107.1883 (16)° | Plate, colourless |
V = 1099.19 (11) Å3 | 0.22 × 0.19 × 0.12 mm |
Z = 4 | |
Data collection top
Bruker D8 VENTURE diffractometer | 3358 independent reflections |
Radiation source: sealed-tube | 2530 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.044 |
φ or ω oscillation scans | θmax = 30.6°, θmin = 3.3° |
Absorption correction: multi-scan Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015 | h = −18→18 |
Tmin = 0.65, Tmax = 0.746 | k = −10→10 |
29038 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | 541 constraints |
R[F2 > 2σ(F2)] = 0.025 | All H-atom parameters refined |
wR(F2) = 0.050 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
S = 1.21 | (Δ/σ)max = 0.010 |
3358 reflections | Δρmax = 0.56 e Å−3 |
181 parameters | Δρmin = −0.45 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.024615 (12) | 0.82947 (2) | 0.394802 (12) | 0.02217 (5) | |
O1 | 0.38303 (8) | 0.52590 (14) | 0.78020 (8) | 0.0189 (3) | |
N1 | 0.52718 (10) | 0.60478 (16) | 0.67938 (10) | 0.0153 (4) | |
N2 | 0.59074 (10) | 0.72289 (15) | 0.54704 (9) | 0.0144 (4) | |
C1 | 0.61605 (12) | 0.62819 (18) | 0.64821 (12) | 0.0147 (5) | |
C2 | 0.72582 (12) | 0.5737 (2) | 0.69912 (12) | 0.0187 (5) | |
C3 | 0.80275 (13) | 0.6186 (2) | 0.64809 (13) | 0.0212 (5) | |
C4 | 0.77407 (13) | 0.7191 (2) | 0.54545 (13) | 0.0207 (5) | |
C5 | 0.66814 (12) | 0.7680 (2) | 0.49653 (12) | 0.0177 (5) | |
C6 | 0.48141 (12) | 0.7597 (2) | 0.51468 (11) | 0.0141 (4) | |
C7 | 0.44317 (12) | 0.68606 (18) | 0.59776 (11) | 0.0136 (4) | |
C8 | 0.33092 (11) | 0.68371 (18) | 0.60273 (11) | 0.0132 (4) | |
C9 | 0.24601 (12) | 0.7562 (2) | 0.51538 (12) | 0.0155 (4) | |
C10 | 0.13902 (12) | 0.7443 (2) | 0.51817 (12) | 0.0171 (5) | |
C11 | 0.11366 (12) | 0.6615 (2) | 0.60756 (13) | 0.0194 (5) | |
C12 | 0.19715 (13) | 0.5897 (2) | 0.69474 (12) | 0.0183 (5) | |
C13 | 0.30551 (12) | 0.59955 (19) | 0.69338 (11) | 0.0153 (5) | |
H2 | 0.7450 (12) | 0.499 (2) | 0.7773 (7) | 0.0224* | |
H3 | 0.8874 (4) | 0.581 (2) | 0.6856 (12) | 0.0254* | |
H4 | 0.8351 (10) | 0.757 (2) | 0.5055 (12) | 0.0248* | |
H5 | 0.6383 (12) | 0.8372 (18) | 0.4168 (6) | 0.0213* | |
H6 | 0.4397 (11) | 0.8335 (17) | 0.4390 (7) | 0.0169* | |
H9 | 0.2633 (12) | 0.8218 (18) | 0.4449 (8) | 0.0186* | |
H11 | 0.0305 (5) | 0.654 (2) | 0.6108 (13) | 0.0233* | |
H12 | 0.1741 (11) | 0.530 (2) | 0.7635 (8) | 0.022* | |
H13 | 0.4517 (8) | 0.526 (3) | 0.7592 (15) | 0.0283* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.01409 (8) | 0.03204 (9) | 0.01871 (8) | 0.00325 (7) | 0.00223 (6) | 0.00481 (7) |
O1 | 0.0236 (6) | 0.0188 (5) | 0.0138 (5) | 0.0002 (5) | 0.0050 (4) | 0.0025 (4) |
N1 | 0.0169 (6) | 0.0145 (6) | 0.0137 (6) | −0.0001 (5) | 0.0032 (5) | 0.0015 (5) |
N2 | 0.0172 (6) | 0.0117 (5) | 0.0141 (6) | −0.0018 (5) | 0.0042 (5) | −0.0016 (5) |
C1 | 0.0163 (8) | 0.0120 (7) | 0.0143 (7) | 0.0003 (5) | 0.0022 (6) | −0.0005 (5) |
C2 | 0.0167 (8) | 0.0190 (8) | 0.0188 (8) | 0.0023 (6) | 0.0029 (6) | −0.0014 (6) |
C3 | 0.0164 (8) | 0.0236 (8) | 0.0224 (8) | 0.0015 (6) | 0.0040 (6) | −0.0041 (6) |
C4 | 0.0189 (8) | 0.0217 (8) | 0.0234 (8) | −0.0011 (6) | 0.0091 (6) | −0.0030 (6) |
C5 | 0.0185 (8) | 0.0173 (7) | 0.0177 (7) | −0.0011 (6) | 0.0060 (6) | −0.0007 (6) |
C6 | 0.0173 (8) | 0.0128 (6) | 0.0119 (7) | −0.0014 (6) | 0.0037 (6) | 0.0017 (5) |
C7 | 0.0154 (7) | 0.0116 (6) | 0.0127 (6) | −0.0008 (5) | 0.0024 (5) | −0.0004 (5) |
C8 | 0.0157 (7) | 0.0111 (6) | 0.0127 (6) | −0.0009 (5) | 0.0038 (5) | 0.0006 (5) |
C9 | 0.0148 (7) | 0.0166 (7) | 0.0143 (7) | −0.0008 (6) | 0.0030 (6) | 0.0019 (6) |
C10 | 0.0154 (8) | 0.0186 (7) | 0.0167 (7) | −0.0010 (6) | 0.0038 (6) | 0.0001 (6) |
C11 | 0.0172 (8) | 0.0221 (7) | 0.0200 (7) | −0.0002 (6) | 0.0072 (6) | 0.0016 (6) |
C12 | 0.0189 (8) | 0.0200 (7) | 0.0179 (8) | −0.0010 (6) | 0.0083 (6) | 0.0014 (6) |
C13 | 0.0190 (8) | 0.0130 (6) | 0.0140 (7) | −0.0011 (6) | 0.0048 (6) | 0.0001 (5) |
Geometric parameters (Å, º) top
Br1—C10 | 1.8967 (11) | C4—C5 | 1.3631 (17) |
O1—C13 | 1.3494 (14) | C6—C7 | 1.385 (2) |
N1—C1 | 1.324 (2) | C7—C8 | 1.4618 (19) |
N1—C7 | 1.3788 (16) | C8—C9 | 1.3993 (16) |
N2—C1 | 1.3938 (17) | C8—C13 | 1.412 (2) |
N2—C5 | 1.368 (2) | C9—C10 | 1.3876 (19) |
N2—C6 | 1.3662 (18) | C10—C11 | 1.393 (2) |
C1—C2 | 1.4185 (17) | C11—C12 | 1.3856 (16) |
C2—C3 | 1.366 (2) | C12—C13 | 1.3988 (19) |
C3—C4 | 1.4294 (18) | | |
| | | |
C1—N1—C7 | 106.16 (12) | C6—C7—C8 | 127.68 (11) |
C1—N2—C5 | 122.30 (11) | C7—C8—C9 | 120.75 (12) |
C1—N2—C6 | 107.91 (12) | C7—C8—C13 | 120.42 (10) |
C5—N2—C6 | 129.77 (12) | C9—C8—C13 | 118.76 (12) |
N1—C1—N2 | 110.14 (11) | C8—C9—C10 | 120.30 (13) |
N1—C1—C2 | 131.26 (12) | Br1—C10—C9 | 119.48 (10) |
N2—C1—C2 | 118.60 (13) | Br1—C10—C11 | 119.36 (9) |
C1—C2—C3 | 118.84 (12) | C9—C10—C11 | 121.07 (11) |
C2—C3—C4 | 121.06 (11) | C10—C11—C12 | 119.16 (12) |
C3—C4—C5 | 119.50 (13) | C11—C12—C13 | 120.72 (13) |
N2—C5—C4 | 119.68 (12) | O1—C13—C8 | 122.03 (12) |
N2—C6—C7 | 105.32 (11) | O1—C13—C12 | 117.97 (12) |
N1—C7—C6 | 110.47 (12) | C8—C13—C12 | 119.99 (11) |
N1—C7—C8 | 121.83 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 1.083 (10) | 2.162 (10) | 3.2349 (15) | 170.1 (11) |
O1—H13···N1 | 0.994 (12) | 1.685 (14) | 2.5987 (18) | 150.8 (14) |
O1—H13···C7 | 0.994 (12) | 2.305 (15) | 2.8711 (18) | 115.1 (10) |
Symmetry code: (i) x, −y+3/2, z−1/2. |
Crystal data top
C19H14B2N2O3·C3H6O | F(000) = 1664 |
Mr = 398.02 | Dx = 1.321 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 99881 reflections |
a = 10.7147 (11) Å | θ = 2.2–29.8° |
b = 34.282 (3) Å | µ = 0.09 mm−1 |
c = 10.9168 (11) Å | T = 100 K |
β = 93.176 (2)° | Block, colourless |
V = 4003.8 (7) Å3 | 0.29 × 0.13 × 0.06 mm |
Z = 8 | |
Data collection top
Bruker D8 VENTURE diffractometer | 21060 independent reflections |
Radiation source: sealed-tube | 9603 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.135 |
φ or ω oscillation scans | θmax = 29.8°, θmin = 2.2° |
Absorption correction: multi-scan Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015 | h = −14→13 |
Tmin = 0.650, Tmax = 0.746 | k = −47→47 |
99881 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.055 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
wR(F2) = 0.102 | (Δ/σ)max = 0.027 |
S = 1.19 | Δρmax = 0.76 e Å−3 |
21060 reflections | Δρmin = −0.71 e Å−3 |
1093 parameters | Absolute structure: 10020 of Friedel pairs used in the refinement |
4 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | |
N1 | 0.5650 (2) | 0.68486 (8) | 0.4050 (2) | 0.0108 (10) | |
N2 | 0.7015 (3) | 0.71855 (8) | 0.3033 (3) | 0.0148 (10) | |
O1 | 0.57633 (19) | 0.63517 (6) | 0.56932 (18) | 0.0139 (7) | |
O2 | 0.3829 (2) | 0.67039 (6) | 0.52069 (19) | 0.0151 (8) | |
O3 | 0.6553 (2) | 0.57292 (6) | 0.6357 (2) | 0.0213 (8) | |
B1 | 0.4913 (4) | 0.65183 (11) | 0.4690 (3) | 0.0128 (13) | |
B2 | 0.5882 (4) | 0.59542 (11) | 0.5536 (4) | 0.0168 (13) | |
C1 | 0.6506 (3) | 0.68188 (9) | 0.3197 (3) | 0.0141 (11) | |
C2 | 0.6922 (3) | 0.65052 (10) | 0.2493 (3) | 0.0199 (13) | |
C3 | 0.7802 (3) | 0.65753 (10) | 0.1660 (3) | 0.0201 (12) | |
C4 | 0.8322 (3) | 0.69524 (10) | 0.1526 (3) | 0.0211 (12) | |
C5 | 0.7909 (3) | 0.72538 (10) | 0.2221 (3) | 0.0193 (12) | |
C6 | 0.6435 (3) | 0.74444 (10) | 0.3787 (3) | 0.0160 (12) | |
C7 | 0.5594 (3) | 0.72356 (10) | 0.4401 (3) | 0.0118 (11) | |
C8 | 0.4712 (3) | 0.73475 (10) | 0.5289 (3) | 0.0129 (12) | |
C9 | 0.4655 (3) | 0.77270 (9) | 0.5762 (3) | 0.0194 (12) | |
C10 | 0.3747 (3) | 0.78317 (10) | 0.6542 (3) | 0.0211 (13) | |
C11 | 0.2876 (3) | 0.75559 (10) | 0.6884 (3) | 0.0214 (13) | |
C12 | 0.2919 (3) | 0.71757 (10) | 0.6449 (3) | 0.0166 (12) | |
C13 | 0.3840 (3) | 0.70663 (9) | 0.5658 (3) | 0.0138 (11) | |
C14 | 0.5151 (3) | 0.58196 (9) | 0.4346 (3) | 0.0139 (11) | |
C15 | 0.5017 (3) | 0.54593 (9) | 0.3744 (3) | 0.0158 (11) | |
C16 | 0.4282 (3) | 0.54349 (9) | 0.2655 (3) | 0.0190 (12) | |
C17 | 0.3694 (3) | 0.57659 (10) | 0.2157 (3) | 0.0208 (12) | |
C18 | 0.3848 (3) | 0.61273 (9) | 0.2750 (3) | 0.0193 (12) | |
C19 | 0.4555 (3) | 0.61533 (9) | 0.3841 (3) | 0.0132 (11) | |
H2 | 0.655194 | 0.621435 | 0.260935 | 0.0239* | |
H3 | 0.810739 | 0.633854 | 0.109256 | 0.0242* | |
H4 | 0.903793 | 0.700148 | 0.088036 | 0.0254* | |
H5 | 0.829136 | 0.754399 | 0.212653 | 0.0231* | |
H6 | 0.661644 | 0.775423 | 0.387105 | 0.0192* | |
H9 | 0.533853 | 0.794113 | 0.551044 | 0.0233* | |
H10 | 0.370771 | 0.812733 | 0.688757 | 0.0253* | |
H11 | 0.215911 | 0.763884 | 0.749509 | 0.0257* | |
H12 | 0.223914 | 0.696376 | 0.672398 | 0.02* | |
H15 | 0.548239 | 0.520231 | 0.4123 | 0.019* | |
H16 | 0.416636 | 0.515687 | 0.219147 | 0.0228* | |
H17 | 0.311902 | 0.574431 | 0.131205 | 0.0249* | |
H18 | 0.341151 | 0.638592 | 0.235064 | 0.0232* | |
H3o | 0.707 (3) | 0.5883 (9) | 0.695 (3) | 0.0319* | |
N3 | 1.0826 (3) | 0.52836 (8) | 0.6940 (3) | 0.0131 (10) | |
N4 | 0.9665 (2) | 0.56530 (8) | 0.8101 (2) | 0.0106 (9) | |
O4 | 0.7608 (2) | 0.67766 (6) | 0.68289 (19) | 0.0151 (8) | |
O5 | 0.8397 (2) | 0.58276 (6) | 0.9799 (2) | 0.0160 (8) | |
O6 | 0.80577 (18) | 0.61667 (5) | 0.78490 (18) | 0.0127 (7) | |
B3 | 0.8996 (4) | 0.59972 (10) | 0.8759 (4) | 0.0123 (12) | |
B4 | 0.8329 (3) | 0.65531 (11) | 0.7624 (3) | 0.0116 (12) | |
C20 | 1.0590 (3) | 0.56631 (9) | 0.7320 (3) | 0.0130 (11) | |
C21 | 1.1283 (3) | 0.59720 (10) | 0.6856 (3) | 0.0177 (12) | |
C22 | 1.2201 (3) | 0.58897 (10) | 0.6061 (3) | 0.0240 (13) | |
C23 | 1.2425 (3) | 0.54977 (10) | 0.5708 (3) | 0.0226 (13) | |
C24 | 1.1735 (3) | 0.52016 (9) | 0.6154 (3) | 0.0171 (12) | |
C25 | 1.0020 (3) | 0.50372 (10) | 0.7506 (3) | 0.0142 (11) | |
C26 | 0.9313 (3) | 0.52655 (9) | 0.8215 (3) | 0.0112 (11) | |
C27 | 0.8368 (3) | 0.51683 (10) | 0.9052 (3) | 0.0117 (12) | |
C28 | 0.7909 (3) | 0.47883 (9) | 0.9170 (3) | 0.0160 (11) | |
C29 | 0.7030 (3) | 0.47008 (11) | 0.9996 (3) | 0.0212 (13) | |
C30 | 0.6586 (3) | 0.49941 (10) | 1.0751 (3) | 0.0198 (12) | |
C31 | 0.7043 (3) | 0.53740 (10) | 1.0657 (3) | 0.0195 (13) | |
C32 | 0.7931 (3) | 0.54636 (10) | 0.9813 (3) | 0.0144 (11) | |
C33 | 0.9488 (3) | 0.66851 (8) | 0.8425 (3) | 0.0127 (11) | |
C34 | 0.9894 (3) | 0.63547 (9) | 0.9102 (3) | 0.0116 (10) | |
C35 | 1.0961 (3) | 0.63834 (9) | 0.9892 (3) | 0.0156 (11) | |
C36 | 1.1614 (3) | 0.67377 (9) | 1.0005 (3) | 0.0152 (11) | |
C37 | 1.1199 (3) | 0.70627 (10) | 0.9334 (3) | 0.0199 (12) | |
C38 | 1.0142 (3) | 0.70367 (9) | 0.8546 (3) | 0.0144 (11) | |
H21 | 1.109779 | 0.627018 | 0.711953 | 0.0213* | |
H22 | 1.275316 | 0.612393 | 0.570438 | 0.0288* | |
H23 | 1.314785 | 0.54344 | 0.508159 | 0.0271* | |
H24 | 1.190652 | 0.490308 | 0.588557 | 0.0205* | |
H25 | 0.996116 | 0.472338 | 0.740471 | 0.017* | |
H28 | 0.825525 | 0.455874 | 0.859745 | 0.0192* | |
H29 | 0.668116 | 0.440553 | 1.006357 | 0.0255* | |
H30 | 0.589275 | 0.49269 | 1.140392 | 0.0238* | |
H31 | 0.670485 | 0.560084 | 1.124399 | 0.0234* | |
H35 | 1.128547 | 0.613175 | 1.041857 | 0.0187* | |
H36 | 1.244281 | 0.675842 | 1.061561 | 0.0182* | |
H37 | 1.170202 | 0.7336 | 0.942694 | 0.0239* | |
H38 | 0.982214 | 0.728961 | 0.802389 | 0.0173* | |
H4o | 0.693 (2) | 0.6635 (9) | 0.638 (3) | 0.0226* | |
N5 | 0.5261 (3) | 0.47235 (8) | 0.7445 (3) | 0.0154 (10) | |
N6 | 0.4157 (2) | 0.43525 (7) | 0.8638 (2) | 0.0121 (9) | |
O7 | 0.26247 (19) | 0.38230 (6) | 0.82645 (18) | 0.0125 (7) | |
O8 | 0.2815 (2) | 0.41484 (6) | 1.02494 (19) | 0.0153 (7) | |
O9 | 0.2297 (2) | 0.32245 (6) | 0.7176 (2) | 0.0152 (8) | |
B5 | 0.3498 (4) | 0.39929 (10) | 0.9228 (4) | 0.0124 (13) | |
B6 | 0.2925 (4) | 0.34415 (10) | 0.8043 (3) | 0.0131 (13) | |
C39 | 0.5057 (3) | 0.43479 (10) | 0.7821 (3) | 0.0147 (12) | |
C40 | 0.5775 (3) | 0.40404 (10) | 0.7362 (3) | 0.0195 (12) | |
C41 | 0.6643 (3) | 0.41278 (10) | 0.6524 (3) | 0.0171 (12) | |
C42 | 0.6816 (3) | 0.45193 (10) | 0.6144 (3) | 0.0236 (13) | |
C43 | 0.6132 (3) | 0.48134 (11) | 0.6628 (3) | 0.0201 (13) | |
C44 | 0.4477 (3) | 0.49616 (10) | 0.8045 (3) | 0.0162 (12) | |
C45 | 0.3781 (3) | 0.47365 (10) | 0.8776 (3) | 0.0147 (12) | |
C46 | 0.2790 (3) | 0.48174 (9) | 0.9593 (3) | 0.0137 (11) | |
C47 | 0.2290 (3) | 0.51913 (9) | 0.9701 (3) | 0.0163 (12) | |
C48 | 0.1346 (3) | 0.52610 (9) | 1.0481 (3) | 0.0174 (12) | |
C49 | 0.0889 (3) | 0.49519 (10) | 1.1181 (3) | 0.0205 (12) | |
C50 | 0.1384 (3) | 0.45812 (9) | 1.1095 (3) | 0.0199 (12) | |
C51 | 0.2342 (3) | 0.45101 (10) | 1.0295 (3) | 0.0166 (12) | |
C52 | 0.4058 (3) | 0.33132 (9) | 0.8893 (3) | 0.0132 (11) | |
C53 | 0.4410 (3) | 0.36437 (9) | 0.9615 (3) | 0.0123 (11) | |
C54 | 0.5438 (3) | 0.36245 (9) | 1.0443 (3) | 0.0158 (11) | |
C55 | 0.6153 (3) | 0.32821 (10) | 1.0559 (3) | 0.0173 (11) | |
C56 | 0.5802 (3) | 0.29566 (9) | 0.9845 (3) | 0.0168 (12) | |
C57 | 0.4767 (3) | 0.29685 (9) | 0.9014 (3) | 0.0183 (12) | |
H40 | 0.564354 | 0.374299 | 0.766329 | 0.0233* | |
H41 | 0.719767 | 0.389698 | 0.61505 | 0.0205* | |
H42 | 0.749029 | 0.458554 | 0.546981 | 0.0284* | |
H43 | 0.628177 | 0.511367 | 0.636534 | 0.0241* | |
H44 | 0.441759 | 0.527574 | 0.795573 | 0.0194* | |
H47 | 0.264832 | 0.54287 | 0.916829 | 0.0196* | |
H48 | 0.095764 | 0.555113 | 1.055456 | 0.0208* | |
H49 | 0.014371 | 0.50054 | 1.179004 | 0.0246* | |
H50 | 0.103477 | 0.434613 | 1.164372 | 0.0239* | |
H54 | 0.569199 | 0.387585 | 1.100399 | 0.019* | |
H55 | 0.696579 | 0.326966 | 1.119325 | 0.0207* | |
H56 | 0.63453 | 0.269079 | 0.993958 | 0.0201* | |
H57 | 0.450962 | 0.271442 | 0.846733 | 0.0219* | |
H9o | 0.157 (2) | 0.3367 (9) | 0.681 (3) | 0.0229* | |
N7 | 0.0112 (2) | 0.31365 (7) | 0.4504 (2) | 0.0098 (9) | |
N8 | 0.1474 (3) | 0.27917 (7) | 0.3486 (3) | 0.0144 (10) | |
O10 | 0.04092 (19) | 0.36405 (6) | 0.60880 (18) | 0.0123 (7) | |
O11 | 0.1348 (2) | 0.42562 (6) | 0.66171 (19) | 0.0167 (8) | |
O12 | −0.1602 (2) | 0.33060 (6) | 0.57772 (19) | 0.0156 (7) | |
B7 | −0.0541 (4) | 0.34770 (10) | 0.5178 (4) | 0.0102 (12) | |
B8 | 0.0550 (4) | 0.40347 (10) | 0.5899 (3) | 0.0123 (12) | |
C58 | 0.0976 (3) | 0.31583 (9) | 0.3645 (3) | 0.0119 (12) | |
C59 | 0.1390 (3) | 0.34725 (9) | 0.2941 (3) | 0.0144 (11) | |
C60 | 0.2288 (3) | 0.34038 (10) | 0.2122 (3) | 0.0173 (12) | |
C61 | 0.2795 (3) | 0.30206 (10) | 0.1990 (3) | 0.0211 (13) | |
C62 | 0.2366 (3) | 0.27220 (10) | 0.2686 (3) | 0.0161 (12) | |
C63 | 0.0912 (3) | 0.25402 (9) | 0.4270 (3) | 0.0125 (11) | |
C64 | 0.0074 (3) | 0.27522 (9) | 0.4903 (3) | 0.0128 (12) | |
C65 | −0.0810 (3) | 0.26481 (9) | 0.5800 (3) | 0.0124 (11) | |
C66 | −0.0908 (3) | 0.22639 (10) | 0.6222 (3) | 0.0173 (12) | |
C67 | −0.1810 (3) | 0.21695 (10) | 0.7024 (3) | 0.0241 (13) | |
C68 | −0.2636 (3) | 0.24530 (10) | 0.7416 (3) | 0.0201 (13) | |
C69 | −0.2527 (3) | 0.28328 (10) | 0.6998 (3) | 0.0199 (12) | |
C70 | −0.1625 (3) | 0.29366 (10) | 0.6198 (3) | 0.0151 (12) | |
C71 | −0.0297 (3) | 0.41745 (9) | 0.4797 (3) | 0.0123 (11) | |
C72 | −0.0959 (3) | 0.38424 (9) | 0.4350 (3) | 0.0124 (11) | |
C73 | −0.1830 (3) | 0.38805 (9) | 0.3370 (3) | 0.0164 (11) | |
C74 | −0.2061 (3) | 0.42456 (9) | 0.2835 (3) | 0.0199 (11) | |
C75 | −0.1393 (3) | 0.45757 (9) | 0.3268 (3) | 0.0188 (12) | |
C76 | −0.0517 (3) | 0.45400 (9) | 0.4237 (3) | 0.0178 (12) | |
H59 | 0.100683 | 0.376214 | 0.304579 | 0.0172* | |
H60 | 0.261636 | 0.364108 | 0.156924 | 0.0208* | |
H61 | 0.35099 | 0.296744 | 0.134656 | 0.0253* | |
H62 | 0.274046 | 0.243072 | 0.259579 | 0.0194* | |
H63 | 0.109881 | 0.223098 | 0.436948 | 0.015* | |
H66 | −0.027647 | 0.204168 | 0.591823 | 0.0208* | |
H67 | −0.187895 | 0.187275 | 0.735359 | 0.029* | |
H68 | −0.335083 | 0.237713 | 0.80376 | 0.0242* | |
H69 | −0.31628 | 0.305334 | 0.73047 | 0.0239* | |
H73 | −0.233322 | 0.362659 | 0.301758 | 0.0197* | |
H74 | −0.275714 | 0.427456 | 0.208311 | 0.0238* | |
H75 | −0.156601 | 0.485724 | 0.284252 | 0.0226* | |
H76 | 0.000256 | 0.479356 | 0.45675 | 0.0214* | |
H11o | 0.177 (3) | 0.4128 (10) | 0.733 (2) | 0.025* | |
O13 | 0.4642 (2) | 0.69217 (7) | 0.0773 (2) | 0.0279 (9) | |
C77 | 0.5040 (3) | 0.68147 (10) | −0.0185 (3) | 0.0217 (13) | |
C78 | 0.5724 (4) | 0.70845 (11) | −0.0996 (3) | 0.0379 (16) | |
C79 | 0.4907 (4) | 0.64038 (10) | −0.0632 (3) | 0.0491 (18) | |
O14 | 0.9242 (3) | 0.63590 (8) | 0.4737 (2) | 0.0551 (12) | |
C80 | 0.9497 (4) | 0.60851 (12) | 0.4117 (4) | 0.0339 (14) | |
C81 | 0.8932 (4) | 0.56969 (12) | 0.4284 (5) | 0.060 (2) | |
C82 | 1.0399 (4) | 0.61136 (13) | 0.3128 (4) | 0.070 (2) | |
O15 | −0.0843 (2) | 0.30769 (7) | 0.1202 (2) | 0.0268 (9) | |
C83 | −0.0458 (3) | 0.32067 (10) | 0.0268 (4) | 0.0268 (14) | |
C84 | 0.0246 (3) | 0.29524 (11) | −0.0574 (3) | 0.0351 (15) | |
C85 | −0.0653 (4) | 0.36248 (11) | −0.0118 (4) | 0.0518 (18) | |
O16 | 0.4803 (2) | 0.44236 (7) | 1.2607 (2) | 0.0403 (10) | |
C86 | 0.4357 (3) | 0.42619 (10) | 1.3456 (3) | 0.0264 (13) | |
C87 | 0.4713 (3) | 0.38551 (11) | 1.3825 (3) | 0.0349 (15) | |
C88 | 0.3415 (4) | 0.44557 (10) | 1.4201 (4) | 0.0445 (16) | |
H78a | 0.615126 | 0.731532 | −0.045012 | 0.0455* | |
H78b | 0.643694 | 0.692445 | −0.143977 | 0.0455* | |
H78c | 0.507667 | 0.720763 | −0.167991 | 0.0455* | |
H79a | 0.435523 | 0.639951 | −0.148688 | 0.059* | |
H79b | 0.581781 | 0.628402 | −0.076739 | 0.059* | |
H79c | 0.445078 | 0.623183 | 0.003798 | 0.059* | |
H81a | 0.965186 | 0.547737 | 0.429356 | 0.0715* | |
H81b | 0.847916 | 0.569024 | 0.513968 | 0.0715* | |
H81c | 0.825489 | 0.564011 | 0.353929 | 0.0715* | |
H82a | 1.011878 | 0.591761 | 0.239257 | 0.0838* | |
H82b | 1.04104 | 0.640806 | 0.278478 | 0.0838* | |
H82c | 1.132006 | 0.60358 | 0.349317 | 0.0838* | |
H84a | 0.122769 | 0.301991 | −0.047214 | 0.0421* | |
H84b | 0.010252 | 0.265067 | −0.034593 | 0.0421* | |
H84c | −0.008765 | 0.300419 | −0.150879 | 0.0421* | |
H85a | −0.09655 | 0.363516 | −0.107221 | 0.0622* | |
H85b | −0.134689 | 0.375642 | 0.042717 | 0.0622* | |
H85c | 0.021461 | 0.378183 | 0.001462 | 0.0622* | |
H87a | 0.416912 | 0.376425 | 1.457458 | 0.0418* | |
H87b | 0.453559 | 0.366166 | 1.305741 | 0.0418* | |
H87c | 0.569185 | 0.384637 | 1.410771 | 0.0418* | |
H88a | 0.335592 | 0.476019 | 1.396203 | 0.0534* | |
H88b | 0.251715 | 0.43202 | 1.401998 | 0.0534* | |
H88c | 0.369126 | 0.442701 | 1.51604 | 0.0534* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0097 (16) | 0.0109 (17) | 0.0122 (17) | −0.0006 (13) | 0.0028 (14) | −0.0034 (13) |
N2 | 0.0173 (18) | 0.0124 (16) | 0.0145 (18) | −0.0022 (14) | 0.0006 (15) | −0.0043 (14) |
O1 | 0.0209 (13) | 0.0044 (11) | 0.0164 (12) | −0.0032 (10) | 0.0002 (11) | −0.0013 (10) |
O2 | 0.0153 (13) | 0.0089 (12) | 0.0216 (14) | −0.0044 (10) | 0.0057 (11) | −0.0029 (10) |
O3 | 0.0320 (16) | 0.0068 (12) | 0.0241 (15) | −0.0009 (11) | −0.0068 (13) | 0.0014 (10) |
B1 | 0.014 (2) | 0.014 (2) | 0.011 (2) | −0.0039 (17) | 0.0041 (19) | −0.0001 (17) |
B2 | 0.017 (2) | 0.016 (2) | 0.018 (2) | −0.0009 (17) | 0.007 (2) | 0.0085 (18) |
C1 | 0.021 (2) | 0.0063 (18) | 0.015 (2) | −0.0039 (15) | 0.0052 (16) | −0.0034 (15) |
C2 | 0.021 (2) | 0.015 (2) | 0.025 (2) | −0.0001 (17) | 0.0120 (19) | −0.0055 (17) |
C3 | 0.020 (2) | 0.016 (2) | 0.026 (2) | −0.0008 (16) | 0.0103 (18) | −0.0020 (17) |
C4 | 0.025 (2) | 0.017 (2) | 0.022 (2) | −0.0003 (17) | 0.0079 (18) | −0.0020 (17) |
C5 | 0.027 (2) | 0.013 (2) | 0.020 (2) | −0.0080 (17) | 0.0109 (18) | −0.0047 (17) |
C6 | 0.024 (2) | 0.0047 (17) | 0.020 (2) | −0.0016 (16) | 0.0066 (18) | −0.0011 (15) |
C7 | 0.012 (2) | 0.0143 (19) | 0.009 (2) | 0.0031 (16) | 0.0011 (16) | −0.0020 (16) |
C8 | 0.012 (2) | 0.010 (2) | 0.017 (2) | −0.0008 (15) | 0.0025 (17) | 0.0007 (16) |
C9 | 0.029 (2) | 0.0068 (18) | 0.023 (2) | 0.0018 (16) | 0.0059 (19) | −0.0039 (16) |
C10 | 0.029 (2) | 0.012 (2) | 0.024 (2) | −0.0012 (18) | 0.0091 (19) | −0.0010 (17) |
C11 | 0.028 (2) | 0.015 (2) | 0.023 (2) | 0.0010 (18) | 0.0075 (19) | −0.0065 (17) |
C12 | 0.017 (2) | 0.014 (2) | 0.019 (2) | −0.0011 (16) | 0.0046 (17) | −0.0001 (16) |
C13 | 0.016 (2) | 0.0092 (18) | 0.016 (2) | 0.0008 (16) | 0.0009 (16) | −0.0019 (15) |
C14 | 0.021 (2) | 0.0037 (16) | 0.017 (2) | −0.0001 (15) | 0.0062 (17) | −0.0031 (15) |
C15 | 0.019 (2) | 0.0064 (17) | 0.022 (2) | −0.0024 (15) | 0.0013 (17) | −0.0034 (16) |
C16 | 0.020 (2) | 0.0111 (18) | 0.026 (2) | −0.0022 (15) | 0.0014 (18) | −0.0085 (16) |
C17 | 0.023 (2) | 0.0149 (19) | 0.024 (2) | −0.0016 (16) | −0.0032 (17) | −0.0062 (16) |
C18 | 0.022 (2) | 0.0103 (18) | 0.025 (2) | −0.0026 (16) | −0.0006 (17) | −0.0031 (16) |
C19 | 0.0142 (19) | 0.0103 (17) | 0.0151 (19) | −0.0008 (15) | −0.0003 (16) | −0.0030 (15) |
N3 | 0.0151 (17) | 0.0066 (15) | 0.0177 (17) | −0.0006 (13) | 0.0029 (14) | 0.0007 (13) |
N4 | 0.0119 (17) | 0.0063 (15) | 0.0139 (17) | −0.0033 (12) | 0.0047 (14) | −0.0020 (13) |
O4 | 0.0196 (14) | 0.0094 (12) | 0.0159 (13) | 0.0000 (10) | −0.0011 (11) | 0.0021 (10) |
O5 | 0.0212 (14) | 0.0079 (12) | 0.0194 (14) | −0.0014 (10) | 0.0053 (12) | −0.0010 (10) |
O6 | 0.0159 (13) | 0.0032 (11) | 0.0192 (13) | −0.0016 (10) | 0.0033 (11) | −0.0004 (10) |
B3 | 0.013 (2) | 0.011 (2) | 0.013 (2) | −0.0017 (17) | 0.0035 (19) | −0.0021 (17) |
B4 | 0.012 (2) | 0.012 (2) | 0.012 (2) | 0.0033 (17) | 0.0103 (19) | −0.0023 (17) |
C20 | 0.018 (2) | 0.0017 (17) | 0.020 (2) | −0.0033 (15) | 0.0029 (17) | −0.0041 (15) |
C21 | 0.023 (2) | 0.0084 (19) | 0.022 (2) | −0.0061 (16) | 0.0114 (18) | −0.0001 (16) |
C22 | 0.026 (2) | 0.017 (2) | 0.030 (2) | −0.0068 (17) | 0.0143 (19) | −0.0037 (17) |
C23 | 0.023 (2) | 0.0123 (19) | 0.035 (2) | −0.0058 (17) | 0.0160 (18) | −0.0062 (17) |
C24 | 0.018 (2) | 0.0067 (18) | 0.027 (2) | 0.0003 (15) | 0.0042 (18) | −0.0016 (16) |
C25 | 0.018 (2) | 0.0066 (18) | 0.018 (2) | −0.0009 (15) | 0.0049 (17) | −0.0038 (15) |
C26 | 0.011 (2) | 0.0112 (18) | 0.012 (2) | −0.0023 (16) | −0.0011 (16) | 0.0076 (15) |
C27 | 0.013 (2) | 0.010 (2) | 0.012 (2) | 0.0013 (15) | 0.0024 (17) | −0.0003 (16) |
C28 | 0.024 (2) | 0.0085 (18) | 0.016 (2) | −0.0018 (16) | 0.0054 (17) | 0.0017 (15) |
C29 | 0.022 (2) | 0.016 (2) | 0.025 (2) | −0.0080 (17) | 0.0021 (18) | 0.0059 (17) |
C30 | 0.019 (2) | 0.022 (2) | 0.020 (2) | −0.0042 (17) | 0.0039 (17) | 0.0086 (17) |
C31 | 0.023 (2) | 0.013 (2) | 0.024 (2) | −0.0015 (17) | 0.0098 (18) | 0.0059 (17) |
C32 | 0.0121 (19) | 0.0166 (19) | 0.015 (2) | 0.0004 (16) | 0.0045 (16) | 0.0043 (16) |
C33 | 0.018 (2) | 0.0062 (17) | 0.0139 (19) | −0.0013 (14) | 0.0052 (16) | −0.0003 (14) |
C34 | 0.0130 (19) | 0.0109 (17) | 0.0110 (18) | 0.0015 (15) | 0.0011 (15) | 0.0007 (14) |
C35 | 0.020 (2) | 0.0105 (18) | 0.0159 (19) | 0.0003 (15) | 0.0013 (16) | −0.0003 (15) |
C36 | 0.019 (2) | 0.0135 (18) | 0.0134 (19) | −0.0038 (15) | 0.0014 (16) | −0.0001 (15) |
C37 | 0.022 (2) | 0.0143 (19) | 0.024 (2) | −0.0047 (16) | 0.0058 (19) | 0.0021 (17) |
C38 | 0.0157 (19) | 0.0115 (18) | 0.0160 (19) | 0.0016 (15) | −0.0003 (16) | 0.0034 (15) |
N5 | 0.0215 (18) | 0.0105 (16) | 0.0140 (17) | −0.0023 (14) | −0.0009 (14) | 0.0020 (13) |
N6 | 0.0180 (17) | 0.0047 (14) | 0.0133 (16) | −0.0001 (12) | −0.0006 (13) | −0.0014 (12) |
O7 | 0.0164 (13) | 0.0032 (11) | 0.0178 (13) | 0.0037 (10) | −0.0013 (11) | 0.0001 (10) |
O8 | 0.0221 (14) | 0.0064 (12) | 0.0176 (13) | 0.0027 (10) | 0.0040 (11) | 0.0022 (10) |
O9 | 0.0169 (14) | 0.0049 (12) | 0.0234 (14) | 0.0009 (9) | −0.0031 (12) | −0.0006 (10) |
B5 | 0.018 (2) | 0.007 (2) | 0.012 (2) | −0.0037 (17) | 0.0010 (19) | 0.0025 (17) |
B6 | 0.019 (2) | 0.011 (2) | 0.011 (2) | −0.0040 (17) | 0.0070 (19) | −0.0003 (17) |
C39 | 0.024 (2) | 0.0033 (19) | 0.017 (2) | −0.0053 (16) | 0.0035 (18) | −0.0017 (16) |
C40 | 0.027 (2) | 0.0118 (19) | 0.020 (2) | −0.0008 (17) | 0.0058 (18) | 0.0000 (16) |
C41 | 0.021 (2) | 0.0114 (19) | 0.019 (2) | −0.0001 (16) | 0.0084 (17) | 0.0018 (16) |
C42 | 0.033 (2) | 0.020 (2) | 0.019 (2) | −0.0057 (19) | 0.0066 (18) | 0.0020 (18) |
C43 | 0.024 (2) | 0.016 (2) | 0.021 (2) | −0.0040 (18) | 0.0092 (19) | 0.0041 (17) |
C44 | 0.023 (2) | 0.0054 (18) | 0.019 (2) | 0.0035 (16) | −0.0027 (18) | 0.0005 (16) |
C45 | 0.015 (2) | 0.016 (2) | 0.013 (2) | −0.0005 (17) | −0.0022 (17) | 0.0025 (17) |
C46 | 0.019 (2) | 0.0025 (17) | 0.019 (2) | −0.0006 (15) | −0.0003 (17) | −0.0007 (15) |
C47 | 0.015 (2) | 0.0068 (19) | 0.026 (2) | 0.0008 (15) | −0.0073 (18) | 0.0003 (16) |
C48 | 0.024 (2) | 0.0065 (17) | 0.022 (2) | 0.0038 (15) | 0.0025 (18) | 0.0000 (16) |
C49 | 0.020 (2) | 0.0170 (19) | 0.025 (2) | 0.0081 (17) | 0.0026 (17) | −0.0034 (17) |
C50 | 0.024 (2) | 0.0105 (19) | 0.026 (2) | 0.0061 (16) | 0.0052 (18) | −0.0009 (16) |
C51 | 0.022 (2) | 0.0090 (19) | 0.018 (2) | −0.0003 (16) | −0.0025 (18) | 0.0041 (16) |
C52 | 0.016 (2) | 0.0091 (17) | 0.0147 (19) | 0.0010 (15) | 0.0027 (16) | 0.0009 (14) |
C53 | 0.0127 (19) | 0.0123 (18) | 0.0123 (18) | −0.0030 (15) | 0.0031 (16) | −0.0001 (15) |
C54 | 0.016 (2) | 0.0139 (18) | 0.017 (2) | −0.0024 (15) | −0.0027 (17) | 0.0011 (16) |
C55 | 0.013 (2) | 0.0188 (19) | 0.019 (2) | 0.0013 (16) | −0.0041 (16) | 0.0016 (16) |
C56 | 0.018 (2) | 0.0159 (19) | 0.016 (2) | 0.0039 (16) | −0.0028 (17) | 0.0046 (16) |
C57 | 0.027 (2) | 0.0094 (18) | 0.018 (2) | 0.0056 (16) | −0.0018 (18) | 0.0004 (15) |
N7 | 0.0195 (17) | 0.0015 (13) | 0.0082 (15) | −0.0002 (12) | −0.0009 (13) | −0.0017 (11) |
N8 | 0.0153 (17) | 0.0071 (15) | 0.0211 (18) | −0.0011 (13) | 0.0025 (14) | −0.0043 (13) |
O10 | 0.0166 (13) | 0.0060 (11) | 0.0144 (12) | −0.0009 (9) | 0.0019 (10) | 0.0006 (10) |
O11 | 0.0220 (14) | 0.0064 (12) | 0.0209 (13) | 0.0001 (10) | −0.0047 (12) | −0.0021 (10) |
O12 | 0.0207 (14) | 0.0075 (11) | 0.0189 (13) | 0.0013 (10) | 0.0043 (11) | 0.0019 (10) |
B7 | 0.011 (2) | 0.0053 (19) | 0.015 (2) | 0.0049 (16) | 0.0023 (19) | 0.0011 (16) |
B8 | 0.012 (2) | 0.010 (2) | 0.015 (2) | 0.0019 (16) | 0.0057 (18) | −0.0044 (16) |
C58 | 0.018 (2) | 0.0034 (18) | 0.014 (2) | −0.0003 (15) | 0.0013 (17) | −0.0047 (16) |
C59 | 0.015 (2) | 0.0072 (17) | 0.021 (2) | −0.0022 (15) | 0.0018 (17) | 0.0007 (15) |
C60 | 0.023 (2) | 0.013 (2) | 0.016 (2) | 0.0010 (16) | 0.0049 (18) | 0.0052 (16) |
C61 | 0.020 (2) | 0.017 (2) | 0.027 (2) | 0.0024 (17) | 0.0082 (18) | −0.0004 (18) |
C62 | 0.022 (2) | 0.0053 (19) | 0.022 (2) | 0.0014 (16) | 0.0107 (18) | −0.0033 (17) |
C63 | 0.019 (2) | 0.0027 (17) | 0.016 (2) | 0.0033 (15) | 0.0012 (17) | 0.0053 (15) |
C64 | 0.020 (2) | 0.0066 (18) | 0.011 (2) | −0.0051 (16) | −0.0008 (17) | 0.0006 (15) |
C65 | 0.020 (2) | 0.0077 (18) | 0.0103 (18) | 0.0012 (15) | 0.0019 (16) | 0.0020 (15) |
C66 | 0.027 (2) | 0.0078 (19) | 0.017 (2) | −0.0009 (17) | 0.0012 (18) | 0.0021 (16) |
C67 | 0.037 (3) | 0.016 (2) | 0.019 (2) | −0.0017 (18) | 0.0061 (19) | 0.0103 (17) |
C68 | 0.019 (2) | 0.022 (2) | 0.020 (2) | 0.0005 (17) | 0.0059 (18) | 0.0047 (17) |
C69 | 0.022 (2) | 0.018 (2) | 0.020 (2) | −0.0035 (17) | 0.0050 (18) | 0.0035 (17) |
C70 | 0.019 (2) | 0.0120 (19) | 0.015 (2) | −0.0021 (16) | 0.0041 (17) | 0.0002 (16) |
C71 | 0.0138 (19) | 0.0075 (18) | 0.0159 (19) | 0.0004 (14) | 0.0042 (15) | 0.0026 (15) |
C72 | 0.0132 (19) | 0.0088 (17) | 0.0154 (19) | −0.0021 (15) | 0.0013 (16) | −0.0013 (15) |
C73 | 0.0173 (19) | 0.0114 (19) | 0.020 (2) | −0.0021 (15) | −0.0052 (16) | 0.0028 (15) |
C74 | 0.023 (2) | 0.0155 (19) | 0.020 (2) | −0.0013 (16) | −0.0063 (17) | 0.0061 (16) |
C75 | 0.024 (2) | 0.0108 (18) | 0.021 (2) | 0.0004 (16) | −0.0026 (17) | 0.0107 (16) |
C76 | 0.023 (2) | 0.0100 (18) | 0.021 (2) | −0.0027 (16) | −0.0002 (18) | 0.0044 (16) |
O13 | 0.0317 (16) | 0.0294 (16) | 0.0236 (15) | 0.0013 (13) | 0.0104 (13) | 0.0025 (13) |
C77 | 0.024 (2) | 0.018 (2) | 0.024 (2) | −0.0032 (17) | 0.0041 (19) | 0.0009 (18) |
C78 | 0.045 (3) | 0.031 (2) | 0.039 (3) | 0.004 (2) | 0.019 (2) | 0.004 (2) |
C79 | 0.062 (4) | 0.029 (2) | 0.058 (3) | −0.010 (2) | 0.024 (3) | −0.017 (2) |
O14 | 0.068 (2) | 0.0473 (19) | 0.0502 (19) | 0.0203 (16) | 0.0072 (17) | −0.0142 (16) |
C80 | 0.035 (2) | 0.033 (3) | 0.035 (3) | 0.007 (2) | 0.015 (2) | 0.005 (2) |
C81 | 0.038 (3) | 0.046 (3) | 0.095 (4) | −0.001 (2) | 0.007 (3) | 0.018 (3) |
C82 | 0.082 (4) | 0.056 (3) | 0.077 (4) | 0.028 (3) | 0.054 (3) | 0.030 (3) |
O15 | 0.0264 (16) | 0.0281 (16) | 0.0266 (16) | −0.0027 (12) | 0.0086 (13) | 0.0015 (13) |
C83 | 0.031 (2) | 0.018 (2) | 0.033 (3) | −0.0042 (18) | 0.006 (2) | −0.0007 (19) |
C84 | 0.036 (3) | 0.029 (2) | 0.041 (3) | 0.001 (2) | 0.014 (2) | −0.007 (2) |
C85 | 0.057 (3) | 0.028 (2) | 0.072 (3) | 0.006 (2) | 0.020 (3) | 0.016 (2) |
O16 | 0.0445 (18) | 0.0305 (15) | 0.0477 (18) | 0.0053 (13) | 0.0199 (15) | 0.0040 (14) |
C86 | 0.030 (2) | 0.017 (2) | 0.033 (2) | −0.0035 (17) | 0.0093 (19) | 0.0008 (18) |
C87 | 0.035 (3) | 0.025 (2) | 0.044 (3) | −0.0037 (19) | −0.004 (2) | 0.000 (2) |
C88 | 0.038 (3) | 0.028 (2) | 0.071 (3) | −0.004 (2) | 0.029 (2) | −0.004 (2) |
Geometric parameters (Å, º) top
N1—B1 | 1.568 (4) | C41—H41 | 1.0833 |
N1—C1 | 1.347 (4) | C42—C43 | 1.369 (5) |
N1—C7 | 1.384 (4) | C42—H42 | 1.0838 |
N2—C1 | 1.386 (4) | C43—H43 | 1.0842 |
N2—C5 | 1.361 (5) | C44—C45 | 1.362 (5) |
N2—C6 | 1.380 (5) | C44—H44 | 1.0815 |
O1—B1 | 1.498 (4) | C45—C46 | 1.450 (5) |
O1—B2 | 1.381 (4) | C46—C47 | 1.397 (4) |
O2—B1 | 1.465 (5) | C46—C51 | 1.403 (5) |
O2—C13 | 1.336 (4) | C47—C48 | 1.379 (5) |
O3—B2 | 1.357 (4) | C47—H47 | 1.0829 |
O3—H3o | 0.98 (3) | C48—C49 | 1.410 (5) |
B1—C19 | 1.591 (5) | C48—H48 | 1.0829 |
B2—C14 | 1.549 (5) | C49—C50 | 1.383 (5) |
C1—C2 | 1.409 (5) | C49—H49 | 1.0826 |
C2—C3 | 1.367 (5) | C50—C51 | 1.405 (5) |
C2—H2 | 1.0825 | C50—H50 | 1.0831 |
C3—C4 | 1.418 (5) | C52—C53 | 1.420 (4) |
C3—H3 | 1.0818 | C52—C57 | 1.407 (4) |
C4—C5 | 1.371 (5) | C53—C54 | 1.387 (4) |
C4—H4 | 1.0835 | C54—C55 | 1.404 (5) |
C5—H5 | 1.0824 | C54—H54 | 1.0831 |
C6—C7 | 1.355 (5) | C55—C56 | 1.400 (5) |
C6—H6 | 1.0841 | C55—H55 | 1.083 |
C7—C8 | 1.442 (5) | C56—C57 | 1.394 (4) |
C8—C9 | 1.404 (5) | C56—H56 | 1.0832 |
C8—C13 | 1.415 (5) | C57—H57 | 1.0829 |
C9—C10 | 1.376 (5) | N7—B7 | 1.565 (5) |
C9—H9 | 1.083 | N7—C58 | 1.356 (4) |
C10—C11 | 1.394 (5) | N7—C64 | 1.389 (4) |
C10—H10 | 1.0821 | N8—C58 | 1.380 (4) |
C11—C12 | 1.388 (5) | N8—C62 | 1.351 (5) |
C11—H11 | 1.0828 | N8—C63 | 1.377 (4) |
C12—C13 | 1.398 (5) | O10—B7 | 1.492 (5) |
C12—H12 | 1.0837 | O10—B8 | 1.378 (4) |
C14—C15 | 1.403 (4) | O11—B8 | 1.359 (4) |
C14—C19 | 1.408 (4) | O11—H11o | 0.98 (3) |
C15—C16 | 1.392 (4) | O12—B7 | 1.465 (5) |
C15—H15 | 1.0831 | O12—C70 | 1.347 (4) |
C16—C17 | 1.394 (5) | B7—C72 | 1.594 (5) |
C16—H16 | 1.083 | B8—C71 | 1.542 (5) |
C17—C18 | 1.403 (5) | C58—C59 | 1.409 (5) |
C17—H17 | 1.083 | C59—C60 | 1.370 (5) |
C18—C19 | 1.379 (4) | C59—H59 | 1.083 |
C18—H18 | 1.0827 | C60—C61 | 1.431 (5) |
N3—C20 | 1.393 (4) | C60—H60 | 1.0826 |
N3—C24 | 1.363 (5) | C61—C62 | 1.370 (5) |
N3—C25 | 1.379 (5) | C61—H61 | 1.0833 |
N4—B3 | 1.574 (5) | C62—H62 | 1.0827 |
N4—C20 | 1.343 (4) | C63—C64 | 1.371 (5) |
N4—C26 | 1.388 (4) | C63—H63 | 1.0831 |
O4—B4 | 1.365 (4) | C64—C65 | 1.444 (5) |
O4—H4o | 0.98 (3) | C65—C66 | 1.401 (5) |
O5—B3 | 1.456 (5) | C65—C70 | 1.405 (5) |
O5—C32 | 1.343 (4) | C66—C67 | 1.379 (5) |
O6—B3 | 1.492 (5) | C66—H66 | 1.0833 |
O6—B4 | 1.381 (4) | C67—C68 | 1.399 (5) |
B3—C34 | 1.591 (5) | C67—H67 | 1.0814 |
B4—C33 | 1.546 (4) | C68—C69 | 1.387 (5) |
C20—C21 | 1.404 (5) | C68—H68 | 1.0828 |
C21—C22 | 1.376 (5) | C69—C70 | 1.385 (5) |
C21—H21 | 1.0832 | C69—H69 | 1.0826 |
C22—C23 | 1.422 (5) | C71—C72 | 1.414 (4) |
C22—H22 | 1.0818 | C71—C76 | 1.408 (4) |
C23—C24 | 1.362 (5) | C72—C73 | 1.386 (4) |
C23—H23 | 1.0834 | C73—C74 | 1.397 (4) |
C24—H24 | 1.083 | C73—H73 | 1.0833 |
C25—C26 | 1.361 (5) | C74—C75 | 1.407 (4) |
C25—H25 | 1.0823 | C74—H74 | 1.0826 |
C26—C27 | 1.440 (5) | C75—C76 | 1.380 (4) |
C27—C28 | 1.400 (5) | C75—H75 | 1.0827 |
C27—C32 | 1.408 (5) | C76—H76 | 1.0833 |
C28—C29 | 1.373 (5) | O13—C77 | 1.208 (4) |
C28—H28 | 1.0832 | C77—C78 | 1.500 (5) |
C29—C30 | 1.399 (5) | C77—C79 | 1.495 (5) |
C29—H29 | 1.0836 | C78—H78a | 1.0761 |
C30—C31 | 1.397 (5) | C78—H78b | 1.078 |
C30—H30 | 1.0823 | C78—H78c | 1.076 |
C31—C32 | 1.395 (5) | C79—H79a | 1.0768 |
C31—H31 | 1.0828 | C79—H79b | 1.0768 |
C33—C34 | 1.408 (4) | C79—H79c | 1.0779 |
C33—C38 | 1.397 (4) | O14—C80 | 1.198 (5) |
C34—C35 | 1.397 (4) | C80—C81 | 1.477 (5) |
C35—C36 | 1.404 (4) | C80—C82 | 1.492 (6) |
C35—H35 | 1.0833 | C81—H81a | 1.0775 |
C36—C37 | 1.394 (5) | C81—H81b | 1.0765 |
C36—H36 | 1.0828 | C81—H81c | 1.077 |
C37—C38 | 1.387 (4) | C82—H82a | 1.0776 |
C37—H37 | 1.082 | C82—H82b | 1.0758 |
C38—H38 | 1.0828 | C82—H82c | 1.0776 |
N5—C39 | 1.372 (4) | O15—C83 | 1.206 (5) |
N5—C43 | 1.361 (5) | C83—C84 | 1.502 (5) |
N5—C44 | 1.365 (5) | C83—C85 | 1.505 (5) |
N6—B5 | 1.576 (5) | C84—H84a | 1.077 |
N6—C39 | 1.349 (4) | C84—H84b | 1.0756 |
N6—C45 | 1.389 (4) | C84—H84c | 1.0774 |
O7—B5 | 1.487 (5) | C85—H85a | 1.0769 |
O7—B6 | 1.370 (4) | C85—H85b | 1.0766 |
O8—B5 | 1.467 (5) | C85—H85c | 1.0767 |
O8—C51 | 1.341 (4) | O16—C86 | 1.201 (4) |
O9—B6 | 1.354 (4) | C86—C87 | 1.496 (5) |
O9—H9o | 0.99 (3) | C86—C88 | 1.488 (5) |
B5—C53 | 1.588 (5) | C87—H87a | 1.0765 |
B6—C52 | 1.551 (5) | C87—H87b | 1.077 |
C39—C40 | 1.414 (5) | C87—H87c | 1.0772 |
C40—C41 | 1.374 (5) | C88—H88a | 1.076 |
C40—H40 | 1.0816 | C88—H88b | 1.0771 |
C41—C42 | 1.418 (5) | C88—H88c | 1.0771 |
| | | |
B1—N1—C1 | 129.2 (3) | N5—C43—C42 | 119.2 (3) |
B1—N1—C7 | 122.7 (2) | N5—C43—H43 | 120.3 |
C1—N1—C7 | 107.8 (3) | C42—C43—H43 | 120.5 |
C1—N2—C5 | 122.5 (3) | N5—C44—C45 | 108.3 (3) |
C1—N2—C6 | 108.2 (3) | N5—C44—H44 | 125.95 |
C5—N2—C6 | 129.3 (3) | C45—C44—H44 | 125.79 |
B1—O1—B2 | 110.0 (3) | N6—C45—C44 | 107.6 (3) |
B1—O2—C13 | 123.7 (3) | N6—C45—C46 | 118.3 (3) |
B2—O3—H3o | 112.9 (18) | C44—C45—C46 | 134.1 (3) |
N1—B1—O1 | 107.5 (3) | C45—C46—C47 | 121.6 (3) |
N1—B1—O2 | 106.7 (2) | C45—C46—C51 | 118.5 (3) |
N1—B1—C19 | 114.8 (3) | C47—C46—C51 | 119.9 (3) |
O1—B1—O2 | 110.3 (2) | C46—C47—C48 | 120.6 (3) |
O1—B1—C19 | 104.1 (2) | C46—C47—H47 | 119.69 |
O2—B1—C19 | 113.3 (3) | C48—C47—H47 | 119.7 |
O1—B2—O3 | 121.9 (3) | C47—C48—C49 | 119.6 (3) |
O1—B2—C14 | 110.6 (3) | C47—C48—H48 | 120.2 |
O3—B2—C14 | 127.5 (3) | C49—C48—H48 | 120.24 |
N1—C1—N2 | 108.0 (3) | C48—C49—C50 | 120.5 (3) |
N1—C1—C2 | 133.1 (3) | C48—C49—H49 | 119.74 |
N2—C1—C2 | 118.9 (3) | C50—C49—H49 | 119.73 |
C1—C2—C3 | 118.7 (3) | C49—C50—C51 | 119.9 (3) |
C1—C2—H2 | 120.66 | C49—C50—H50 | 120.06 |
C3—C2—H2 | 120.68 | C51—C50—H50 | 120.07 |
C2—C3—C4 | 121.2 (3) | O8—C51—C46 | 122.2 (3) |
C2—C3—H3 | 119.41 | O8—C51—C50 | 118.3 (3) |
C4—C3—H3 | 119.39 | C46—C51—C50 | 119.5 (3) |
C3—C4—C5 | 119.4 (3) | B6—C52—C53 | 106.3 (3) |
C3—C4—H4 | 120.41 | B6—C52—C57 | 134.1 (3) |
C5—C4—H4 | 120.23 | C53—C52—C57 | 119.5 (3) |
N2—C5—C4 | 119.4 (3) | B5—C53—C52 | 108.3 (3) |
N2—C5—H5 | 120.28 | B5—C53—C54 | 131.6 (3) |
C4—C5—H5 | 120.35 | C52—C53—C54 | 120.0 (3) |
N2—C6—C7 | 106.9 (3) | C53—C54—C55 | 120.6 (3) |
N2—C6—H6 | 126.56 | C53—C54—H54 | 119.74 |
C7—C6—H6 | 126.54 | C55—C54—H54 | 119.71 |
N1—C7—C6 | 109.1 (3) | C54—C55—C56 | 119.2 (3) |
N1—C7—C8 | 118.6 (3) | C54—C55—H55 | 120.39 |
C6—C7—C8 | 132.2 (3) | C56—C55—H55 | 120.43 |
C7—C8—C9 | 122.4 (3) | C55—C56—C57 | 121.2 (3) |
C7—C8—C13 | 118.7 (3) | C55—C56—H56 | 119.39 |
C9—C8—C13 | 118.9 (3) | C57—C56—H56 | 119.38 |
C8—C9—C10 | 121.1 (3) | C52—C57—C56 | 119.4 (3) |
C8—C9—H9 | 119.46 | C52—C57—H57 | 120.27 |
C10—C9—H9 | 119.4 | C56—C57—H57 | 120.28 |
C9—C10—C11 | 119.7 (3) | B7—N7—C58 | 128.6 (3) |
C9—C10—H10 | 120.2 | B7—N7—C64 | 122.6 (3) |
C11—C10—H10 | 120.13 | C58—N7—C64 | 107.6 (2) |
C10—C11—C12 | 120.7 (3) | C58—N8—C62 | 122.3 (3) |
C10—C11—H11 | 119.68 | C58—N8—C63 | 107.9 (3) |
C12—C11—H11 | 119.67 | C62—N8—C63 | 129.8 (3) |
C11—C12—C13 | 120.1 (3) | B7—O10—B8 | 110.2 (2) |
C11—C12—H12 | 119.98 | B8—O11—H11o | 117 (2) |
C13—C12—H12 | 119.91 | B7—O12—C70 | 123.9 (3) |
O2—C13—C8 | 121.3 (3) | N7—B7—O10 | 106.7 (3) |
O2—C13—C12 | 119.0 (3) | N7—B7—O12 | 106.8 (2) |
C8—C13—C12 | 119.5 (3) | N7—B7—C72 | 116.0 (3) |
B2—C14—C15 | 133.5 (3) | O10—B7—O12 | 111.8 (3) |
B2—C14—C19 | 106.5 (3) | O10—B7—C72 | 104.0 (2) |
C15—C14—C19 | 120.0 (3) | O12—B7—C72 | 111.5 (3) |
C14—C15—C16 | 119.4 (3) | O10—B8—O11 | 122.2 (3) |
C14—C15—H15 | 120.28 | O10—B8—C71 | 110.9 (3) |
C16—C15—H15 | 120.28 | O11—B8—C71 | 126.9 (3) |
C15—C16—C17 | 120.4 (3) | N7—C58—N8 | 108.7 (3) |
C15—C16—H16 | 119.78 | N7—C58—C59 | 131.8 (3) |
C17—C16—H16 | 119.79 | N8—C58—C59 | 119.5 (3) |
C16—C17—C18 | 120.0 (3) | C58—C59—C60 | 118.6 (3) |
C16—C17—H17 | 119.98 | C58—C59—H59 | 120.71 |
C18—C17—H17 | 120.03 | C60—C59—H59 | 120.69 |
C17—C18—C19 | 120.0 (3) | C59—C60—C61 | 120.5 (3) |
C17—C18—H18 | 120 | C59—C60—H60 | 119.8 |
C19—C18—H18 | 119.96 | C61—C60—H60 | 119.72 |
B1—C19—C14 | 108.7 (3) | C60—C61—C62 | 119.3 (3) |
B1—C19—C18 | 131.1 (3) | C60—C61—H61 | 120.45 |
C14—C19—C18 | 120.1 (3) | C62—C61—H61 | 120.24 |
C20—N3—C24 | 121.9 (3) | N8—C62—C61 | 119.8 (3) |
C20—N3—C25 | 108.1 (3) | N8—C62—H62 | 120.06 |
C24—N3—C25 | 130.0 (3) | C61—C62—H62 | 120.14 |
B3—N4—C20 | 129.9 (3) | N8—C63—C64 | 107.6 (3) |
B3—N4—C26 | 122.9 (3) | N8—C63—H63 | 126.19 |
C20—N4—C26 | 107.2 (3) | C64—C63—H63 | 126.2 |
B4—O4—H4o | 114.6 (18) | N7—C64—C63 | 108.3 (3) |
B3—O5—C32 | 124.0 (3) | N7—C64—C65 | 118.6 (3) |
B3—O6—B4 | 110.6 (2) | C63—C64—C65 | 133.1 (3) |
N4—B3—O5 | 106.8 (2) | C64—C65—C66 | 121.3 (3) |
N4—B3—O6 | 107.2 (3) | C64—C65—C70 | 118.5 (3) |
N4—B3—C34 | 113.6 (3) | C66—C65—C70 | 120.1 (3) |
O5—B3—O6 | 111.4 (3) | C65—C66—C67 | 119.9 (3) |
O5—B3—C34 | 114.3 (3) | C65—C66—H66 | 120.08 |
O6—B3—C34 | 103.4 (2) | C67—C66—H66 | 120 |
O4—B4—O6 | 122.3 (3) | C66—C67—C68 | 120.5 (3) |
O4—B4—C33 | 127.1 (3) | C66—C67—H67 | 119.76 |
O6—B4—C33 | 110.5 (3) | C68—C67—H67 | 119.73 |
N3—C20—N4 | 108.5 (3) | C67—C68—C69 | 119.1 (3) |
N3—C20—C21 | 119.3 (3) | C67—C68—H68 | 120.4 |
N4—C20—C21 | 132.2 (3) | C69—C68—H68 | 120.47 |
C20—C21—C22 | 119.0 (3) | C68—C69—C70 | 121.6 (3) |
C20—C21—H21 | 120.51 | C68—C69—H69 | 119.18 |
C22—C21—H21 | 120.53 | C70—C69—H69 | 119.24 |
C21—C22—C23 | 120.1 (3) | O12—C70—C65 | 122.2 (3) |
C21—C22—H22 | 119.98 | O12—C70—C69 | 118.9 (3) |
C23—C22—H22 | 119.94 | C65—C70—C69 | 118.7 (3) |
C22—C23—C24 | 120.3 (3) | B8—C71—C72 | 106.3 (3) |
C22—C23—H23 | 119.9 | B8—C71—C76 | 133.8 (3) |
C24—C23—H23 | 119.77 | C72—C71—C76 | 119.9 (3) |
N3—C24—C23 | 119.5 (3) | B7—C72—C71 | 108.5 (3) |
N3—C24—H24 | 120.22 | B7—C72—C73 | 131.9 (3) |
C23—C24—H24 | 120.3 | C71—C72—C73 | 119.6 (3) |
N3—C25—C26 | 106.5 (3) | C72—C73—C74 | 120.2 (3) |
N3—C25—H25 | 126.7 | C72—C73—H73 | 119.93 |
C26—C25—H25 | 126.79 | C74—C73—H73 | 119.88 |
N4—C26—C25 | 109.7 (3) | C73—C74—C75 | 120.3 (3) |
N4—C26—C27 | 118.9 (3) | C73—C74—H74 | 119.84 |
C25—C26—C27 | 131.3 (3) | C75—C74—H74 | 119.82 |
C26—C27—C28 | 122.5 (3) | C74—C75—C76 | 119.9 (3) |
C26—C27—C32 | 118.4 (3) | C74—C75—H75 | 120.08 |
C28—C27—C32 | 119.1 (3) | C76—C75—H75 | 120.06 |
C27—C28—C29 | 121.4 (3) | C71—C76—C75 | 120.1 (3) |
C27—C28—H28 | 119.28 | C71—C76—H76 | 119.92 |
C29—C28—H28 | 119.35 | C75—C76—H76 | 119.95 |
C28—C29—C30 | 119.9 (3) | O13—C77—C78 | 122.1 (3) |
C28—C29—H29 | 120.03 | O13—C77—C79 | 122.4 (3) |
C30—C29—H29 | 120.07 | C78—C77—C79 | 115.4 (3) |
C29—C30—C31 | 119.6 (3) | C77—C78—H78a | 109.43 |
C29—C30—H30 | 120.23 | C77—C78—H78b | 109.38 |
C31—C30—H30 | 120.17 | C77—C78—H78c | 109.48 |
C30—C31—C32 | 120.6 (3) | H78a—C78—H78b | 109.46 |
C30—C31—H31 | 119.73 | H78a—C78—H78c | 109.61 |
C32—C31—H31 | 119.66 | H78b—C78—H78c | 109.46 |
O5—C32—C27 | 121.7 (3) | C77—C79—H79a | 109.52 |
O5—C32—C31 | 118.7 (3) | C77—C79—H79b | 109.51 |
C27—C32—C31 | 119.4 (3) | C77—C79—H79c | 109.46 |
B4—C33—C34 | 106.0 (3) | H79a—C79—H79b | 109.5 |
B4—C33—C38 | 133.6 (3) | H79a—C79—H79c | 109.41 |
C34—C33—C38 | 120.4 (3) | H79b—C79—H79c | 109.42 |
B3—C34—C33 | 109.4 (3) | O14—C80—C81 | 121.9 (4) |
B3—C34—C35 | 131.6 (3) | O14—C80—C82 | 122.3 (3) |
C33—C34—C35 | 119.1 (3) | C81—C80—C82 | 115.8 (3) |
C34—C35—C36 | 120.1 (3) | C80—C81—H81a | 109.42 |
C34—C35—H35 | 119.94 | C80—C81—H81b | 109.51 |
C36—C35—H35 | 119.92 | C80—C81—H81c | 109.48 |
C35—C36—C37 | 120.2 (3) | H81a—C81—H81b | 109.47 |
C35—C36—H36 | 119.91 | H81a—C81—H81c | 109.43 |
C37—C36—H36 | 119.87 | H81b—C81—H81c | 109.51 |
C36—C37—C38 | 120.0 (3) | C80—C82—H82a | 109.43 |
C36—C37—H37 | 120.01 | C80—C82—H82b | 109.56 |
C38—C37—H37 | 119.99 | C80—C82—H82c | 109.42 |
C33—C38—C37 | 120.2 (3) | H82a—C82—H82b | 109.51 |
C33—C38—H38 | 119.91 | H82a—C82—H82c | 109.38 |
C37—C38—H38 | 119.89 | H82b—C82—H82c | 109.52 |
C39—N5—C43 | 122.3 (3) | O15—C83—C84 | 120.6 (3) |
C39—N5—C44 | 107.8 (3) | O15—C83—C85 | 122.7 (3) |
C43—N5—C44 | 129.9 (3) | C84—C83—C85 | 116.7 (3) |
B5—N6—C39 | 127.9 (3) | C83—C84—H84a | 109.38 |
B5—N6—C45 | 124.0 (3) | C83—C84—H84b | 109.53 |
C39—N6—C45 | 107.7 (3) | C83—C84—H84c | 109.36 |
B5—O7—B6 | 110.7 (3) | H84a—C84—H84b | 109.57 |
B5—O8—C51 | 124.7 (3) | H84a—C84—H84c | 109.44 |
B6—O9—H9o | 111.2 (18) | H84b—C84—H84c | 109.55 |
N6—B5—O7 | 107.2 (3) | C83—C85—H85a | 109.42 |
N6—B5—O8 | 106.3 (2) | C83—C85—H85b | 109.46 |
N6—B5—C53 | 114.5 (3) | C83—C85—H85c | 109.41 |
O7—B5—O8 | 111.0 (3) | H85a—C85—H85b | 109.51 |
O7—B5—C53 | 104.3 (3) | H85a—C85—H85c | 109.5 |
O8—B5—C53 | 113.4 (3) | H85b—C85—H85c | 109.53 |
O7—B6—O9 | 122.4 (3) | O16—C86—C87 | 122.1 (3) |
O7—B6—C52 | 110.4 (3) | O16—C86—C88 | 121.8 (3) |
O9—B6—C52 | 127.1 (3) | C87—C86—C88 | 116.1 (3) |
N5—C39—N6 | 108.6 (3) | C86—C87—H87a | 109.49 |
N5—C39—C40 | 119.7 (3) | C86—C87—H87b | 109.46 |
N6—C39—C40 | 131.7 (3) | C86—C87—H87c | 109.42 |
C39—C40—C41 | 118.3 (3) | H87a—C87—H87b | 109.51 |
C39—C40—H40 | 120.83 | H87a—C87—H87c | 109.5 |
C41—C40—H40 | 120.9 | H87b—C87—H87c | 109.46 |
C40—C41—C42 | 120.4 (3) | C86—C88—H88a | 109.47 |
C40—C41—H41 | 119.73 | C86—C88—H88b | 109.42 |
C42—C41—H41 | 119.84 | C86—C88—H88c | 109.4 |
C41—C42—C43 | 120.1 (3) | H88a—C88—H88b | 109.54 |
C41—C42—H42 | 120.02 | H88a—C88—H88c | 109.54 |
C43—C42—H42 | 119.89 | H88b—C88—H88c | 109.45 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5i | 1.08 | 2.28 | 3.353 (4) | 170.17 |
C6—H6···O9ii | 1.08 | 2.33 | 3.205 (4) | 136.95 |
O3—H3o···O6 | 0.98 (3) | 1.71 (3) | 2.685 (3) | 174 (3) |
C22—H22···O2iii | 1.08 | 2.38 | 3.446 (4) | 169.89 |
C24—H24···O11iii | 1.08 | 2.44 | 3.310 (4) | 136.15 |
C25—H25···O11iii | 1.08 | 2.38 | 3.207 (4) | 132.22 |
C30—H30···O16 | 1.08 | 2.50 | 3.465 (4) | 148.35 |
C36—H36···O13iv | 1.08 | 2.42 | 3.365 (4) | 145.23 |
O4—H4o···O1 | 0.98 (3) | 1.72 (3) | 2.701 (3) | 175 (3) |
C41—H41···O12iii | 1.08 | 2.45 | 3.509 (4) | 166.60 |
C43—H43···O3 | 1.08 | 2.13 | 3.189 (4) | 164.82 |
C55—H55···O15iv | 1.08 | 2.44 | 3.331 (4) | 138.86 |
O9—H9o···O10 | 0.99 (3) | 1.71 (3) | 2.696 (3) | 174 (3) |
C60—H60···O8i | 1.08 | 2.28 | 3.338 (4) | 166.22 |
C62—H62···O4v | 1.08 | 2.36 | 3.284 (4) | 141.81 |
C68—H68···O13vi | 1.08 | 2.50 | 3.510 (4) | 155.16 |
O11—H11o···O7 | 0.98 (3) | 1.70 (3) | 2.654 (3) | 164 (3) |
C78—H78b···O4i | 1.08 | 2.38 | 3.371 (4) | 152.05 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, y+1/2, −z+1; (iii) x+1, y, z; (iv) x+1, y, z+1; (v) −x+1, y−1/2, −z+1; (vi) −x, y−1/2, −z+1. |
Crystal data top
2(C20H16B2N2O4)·C3H6O | F(000) = 1664 |
Mr = 798.01 | Dx = 1.296 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -C 2yc | Cell parameters from 9873 reflections |
a = 21.8035 (16) Å | θ = 4.4–77.2° |
b = 10.4647 (8) Å | µ = 0.73 mm−1 |
c = 19.3032 (14) Å | T = 100 K |
β = 111.794 (3)° | Plate, colourless |
V = 4089.6 (5) Å3 | 0.29 × 0.13 × 0.06 mm |
Z = 4 | |
Data collection top
Bruker D8 VENTURE diffractometer | 4107 independent reflections |
Radiation source: microfocus source | 3264 reflections with I > 3σ(I) |
Multi-layer optics monochromator | Rint = 0.052 |
φ or ω oscillation scans | θmax = 77.3°, θmin = 4.4° |
Absorption correction: multi-scan Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015 | h = −15→26 |
Tmin = 0.688, Tmax = 0.744 | k = −11→12 |
17247 measured reflections | l = −23→22 |
Refinement top
Refinement on F2 | 1080 constraints |
R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.154 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
S = 2.59 | (Δ/σ)max = 0.046 |
4107 reflections | Δρmax = 0.33 e Å−3 |
333 parameters | Δρmin = −0.43 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.74274 (9) | −0.07530 (17) | −0.03909 (11) | 0.0550 (9) | |
O2 | 0.54439 (7) | 0.60890 (12) | 0.08611 (7) | 0.0267 (5) | |
O3 | 0.61182 (7) | 0.22760 (12) | 0.02899 (7) | 0.0232 (5) | |
O4 | 0.54555 (7) | 0.38757 (12) | 0.05509 (7) | 0.0253 (5) | |
N1 | 0.53967 (8) | 0.15995 (15) | 0.09284 (8) | 0.0223 (6) | |
N2 | 0.47974 (9) | 0.03701 (19) | 0.13639 (9) | 0.0349 (7) | |
C1 | 0.49301 (10) | 0.1621 (2) | 0.12277 (12) | 0.0317 (8) | |
C2 | 0.45888 (14) | 0.2625 (3) | 0.14070 (17) | 0.0517 (11) | |
C3 | 0.41441 (15) | 0.2350 (3) | 0.17301 (18) | 0.0684 (14) | |
C4 | 0.40290 (16) | 0.1062 (4) | 0.18777 (17) | 0.0721 (15) | |
C5 | 0.43496 (14) | 0.0089 (3) | 0.16868 (14) | 0.0527 (11) | |
C6 | 0.51884 (11) | −0.0435 (2) | 0.11367 (11) | 0.0286 (7) | |
C7 | 0.55590 (9) | 0.03331 (18) | 0.08748 (10) | 0.0209 (6) | |
C8 | 0.60581 (9) | 0.00523 (18) | 0.05668 (10) | 0.0202 (6) | |
C9 | 0.62680 (10) | −0.11971 (19) | 0.05130 (11) | 0.0255 (7) | |
C10 | 0.67249 (11) | −0.1443 (2) | 0.01947 (13) | 0.0329 (8) | |
C11 | 0.69858 (11) | −0.0421 (2) | −0.00820 (13) | 0.0350 (8) | |
C12 | 0.67910 (11) | 0.0823 (2) | −0.00308 (12) | 0.0289 (8) | |
C13 | 0.63197 (9) | 0.10695 (17) | 0.02880 (10) | 0.0203 (6) | |
C14 | 0.7678 (2) | 0.0232 (3) | −0.0722 (3) | 0.080 (2) | |
C15 | 0.62853 (10) | 0.44673 (18) | 0.17352 (10) | 0.0217 (6) | |
C16 | 0.63876 (9) | 0.31582 (18) | 0.16308 (10) | 0.0207 (6) | |
C17 | 0.69048 (10) | 0.25151 (19) | 0.21700 (10) | 0.0245 (7) | |
C18 | 0.73122 (10) | 0.3153 (2) | 0.28114 (11) | 0.0293 (7) | |
C19 | 0.72064 (11) | 0.4444 (2) | 0.29193 (11) | 0.0288 (7) | |
C20 | 0.66957 (10) | 0.51095 (19) | 0.23783 (11) | 0.0258 (7) | |
B1 | 0.56966 (11) | 0.4906 (2) | 0.10248 (12) | 0.0227 (7) | |
B2 | 0.58504 (11) | 0.2718 (2) | 0.08456 (12) | 0.0216 (7) | |
H2 | 0.4678 (15) | 0.339 (3) | 0.1327 (17) | 0.0621* | |
H3 | 0.3840 (15) | 0.307 (3) | 0.1830 (16) | 0.0821* | |
H4 | 0.3691 (17) | 0.089 (3) | 0.2082 (17) | 0.0865* | |
H5 | 0.4323 (14) | −0.0922 (6) | 0.1790 (14) | 0.0633* | |
H6 | 0.5207 (11) | −0.1460 (4) | 0.1209 (12) | 0.0344* | |
H9 | 0.6089 (10) | −0.2018 (12) | 0.0724 (11) | 0.0306* | |
H10 | 0.6890 (11) | −0.2416 (8) | 0.0181 (12) | 0.0394* | |
H12 | 0.6939 (10) | 0.1598 (14) | −0.0306 (11) | 0.0347* | |
H14a | 0.7343 (13) | 0.084 (3) | −0.1146 (13) | 0.0965* | |
H14b | 0.8000 (13) | 0.077 (3) | −0.0251 (11) | 0.0965* | |
H14c | 0.8005 (13) | −0.018 (3) | −0.0963 (17) | 0.0965* | |
H17 | 0.6986 (11) | 0.1525 (7) | 0.2064 (11) | 0.0294* | |
H18 | 0.7692 (8) | 0.2647 (17) | 0.3255 (8) | 0.0351* | |
H19 | 0.7512 (9) | 0.4913 (17) | 0.3432 (6) | 0.0346* | |
H20 | 0.6572 (11) | 0.6092 (7) | 0.2445 (12) | 0.031* | |
H21 | 0.5115 (10) | 0.616 (2) | 0.0351 (6) | 0.0401* | |
O5 | 0.4620 (3) | −0.2366 (4) | 0.2304 (3) | 0.106 (3) | 0.5 |
C21 | 0.5 | −0.4468 (3) | 0.25 | 0.0466 (15) | |
C22 | 0.4567 (3) | −0.3476 (4) | 0.2090 (3) | 0.047 (2) | 0.5 |
C23 | 0.4046 (3) | −0.3821 (5) | 0.1357 (3) | 0.052 (2) | 0.5 |
H23a | 0.371718 | −0.30223 | 0.114847 | 0.0629* | 0.5 |
H23b | 0.427444 | −0.405675 | 0.096497 | 0.0629* | 0.5 |
H23c | 0.3771 | −0.463143 | 0.142786 | 0.0629* | 0.5 |
H21a | 0.471305 | −0.524751 | 0.25851 | 0.0559* | 0.5 |
H21b | 0.529128 | −0.480241 | 0.219188 | 0.0559* | 0.5 |
H21c | 0.532198 | −0.410238 | 0.303244 | 0.0559* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0505 (11) | 0.0451 (10) | 0.0919 (15) | −0.0053 (9) | 0.0525 (11) | −0.0223 (10) |
O2 | 0.0329 (8) | 0.0178 (7) | 0.0256 (7) | 0.0016 (6) | 0.0064 (6) | −0.0031 (6) |
O3 | 0.0307 (8) | 0.0197 (7) | 0.0224 (7) | −0.0020 (6) | 0.0135 (6) | −0.0005 (5) |
O4 | 0.0270 (7) | 0.0211 (7) | 0.0220 (7) | 0.0035 (6) | 0.0026 (6) | −0.0049 (5) |
N1 | 0.0228 (8) | 0.0239 (8) | 0.0221 (8) | −0.0045 (7) | 0.0107 (7) | −0.0080 (6) |
N2 | 0.0362 (11) | 0.0483 (11) | 0.0282 (9) | −0.0217 (9) | 0.0213 (8) | −0.0171 (8) |
C1 | 0.0294 (11) | 0.0371 (12) | 0.0354 (11) | −0.0126 (10) | 0.0199 (9) | −0.0219 (9) |
C2 | 0.0391 (14) | 0.0577 (18) | 0.0722 (18) | −0.0196 (13) | 0.0367 (13) | −0.0456 (16) |
C3 | 0.0487 (17) | 0.089 (2) | 0.090 (2) | −0.0361 (17) | 0.0515 (16) | −0.066 (2) |
C4 | 0.0585 (19) | 0.112 (3) | 0.072 (2) | −0.0498 (19) | 0.0539 (16) | −0.064 (2) |
C5 | 0.0560 (16) | 0.075 (2) | 0.0448 (14) | −0.0397 (16) | 0.0397 (13) | −0.0316 (14) |
C6 | 0.0379 (12) | 0.0289 (11) | 0.0229 (10) | −0.0128 (10) | 0.0158 (9) | −0.0051 (8) |
C7 | 0.0213 (9) | 0.0255 (9) | 0.0161 (8) | −0.0034 (8) | 0.0071 (7) | −0.0040 (7) |
C8 | 0.0221 (9) | 0.0191 (9) | 0.0193 (9) | −0.0009 (7) | 0.0077 (7) | 0.0011 (7) |
C9 | 0.0241 (10) | 0.0203 (10) | 0.0298 (10) | 0.0019 (8) | 0.0074 (8) | −0.0011 (8) |
C10 | 0.0281 (11) | 0.0238 (10) | 0.0485 (13) | 0.0022 (9) | 0.0164 (10) | −0.0049 (9) |
C11 | 0.0298 (11) | 0.0321 (12) | 0.0503 (13) | −0.0022 (10) | 0.0231 (10) | −0.0114 (10) |
C12 | 0.0328 (11) | 0.0263 (11) | 0.0360 (11) | −0.0037 (9) | 0.0226 (9) | −0.0058 (8) |
C13 | 0.0230 (9) | 0.0190 (9) | 0.0211 (9) | −0.0014 (8) | 0.0106 (7) | −0.0012 (7) |
C14 | 0.089 (3) | 0.064 (2) | 0.135 (3) | −0.028 (2) | 0.096 (3) | −0.039 (2) |
C15 | 0.0216 (9) | 0.0217 (10) | 0.0209 (9) | −0.0026 (8) | 0.0069 (8) | −0.0026 (7) |
C16 | 0.0213 (9) | 0.0196 (9) | 0.0231 (9) | −0.0003 (8) | 0.0104 (8) | −0.0002 (7) |
C17 | 0.0252 (10) | 0.0234 (10) | 0.0229 (10) | −0.0009 (8) | 0.0067 (8) | −0.0006 (8) |
C18 | 0.0264 (10) | 0.0301 (11) | 0.0245 (10) | 0.0006 (9) | 0.0016 (8) | −0.0004 (8) |
C19 | 0.0296 (11) | 0.0280 (11) | 0.0232 (10) | −0.0037 (9) | 0.0033 (8) | −0.0024 (8) |
C20 | 0.0266 (10) | 0.0254 (10) | 0.0222 (10) | −0.0043 (9) | 0.0052 (8) | −0.0045 (8) |
B1 | 0.0256 (11) | 0.0206 (11) | 0.0242 (10) | 0.0015 (9) | 0.0119 (9) | −0.0008 (8) |
B2 | 0.0224 (11) | 0.0207 (10) | 0.0221 (10) | 0.0017 (9) | 0.0086 (8) | 0.0003 (8) |
O5 | 0.159 (6) | 0.031 (2) | 0.086 (4) | 0.002 (3) | −0.002 (4) | 0.003 (2) |
C21 | 0.050 (2) | 0.039 (2) | 0.055 (2) | 0 | 0.0242 (18) | 0 |
C22 | 0.066 (3) | 0.026 (2) | 0.046 (3) | 0.005 (2) | 0.019 (3) | 0.005 (2) |
C23 | 0.056 (3) | 0.057 (3) | 0.045 (3) | 0.005 (3) | 0.020 (3) | 0.019 (3) |
Geometric parameters (Å, º) top
O1—C11 | 1.352 (3) | C8—C13 | 1.407 (3) |
O1—C14 | 1.424 (5) | C9—C10 | 1.375 (3) |
O2—B1 | 1.344 (2) | C10—C11 | 1.407 (3) |
O3—C13 | 1.337 (2) | C11—C12 | 1.384 (3) |
O4—B1 | 1.385 (2) | C12—C13 | 1.404 (3) |
N1—C1 | 1.344 (3) | C15—C16 | 1.414 (3) |
N1—C7 | 1.385 (3) | C15—C20 | 1.404 (2) |
N1—B2 | 1.578 (3) | C15—B1 | 1.558 (2) |
N2—C1 | 1.387 (3) | C16—C17 | 1.392 (2) |
N2—C5 | 1.371 (3) | C16—B2 | 1.601 (2) |
N2—C6 | 1.380 (3) | C17—C18 | 1.396 (2) |
C1—C2 | 1.402 (4) | C18—C19 | 1.399 (3) |
C2—C3 | 1.365 (5) | C19—C20 | 1.397 (3) |
C2—H2 | 0.85 (3) | O5—O5i | 1.545 (8) |
C3—C4 | 1.419 (5) | O5—C22 | 1.224 (6) |
C4—C5 | 1.362 (5) | C21—C22 | 1.428 (5) |
C4—H4 | 0.97 (5) | C21—C22i | 1.428 (5) |
C6—C7 | 1.364 (3) | C22—C23 | 1.493 (7) |
C7—C8 | 1.451 (3) | C22—H21ci | 0.7659 |
C8—C9 | 1.401 (3) | H21a—H21bi | 0.6367 |
| | | |
C11—O1—C14 | 117.8 (3) | O1—C11—C12 | 124.1 (2) |
C1—N1—C7 | 107.67 (19) | C10—C11—C12 | 120.6 (2) |
C1—N1—B2 | 129.28 (19) | C11—C12—C13 | 119.9 (2) |
C7—N1—B2 | 121.03 (18) | O3—C13—C8 | 122.2 (2) |
C1—N2—C5 | 121.5 (2) | O3—C13—C12 | 118.02 (19) |
C1—N2—C6 | 108.6 (2) | C8—C13—C12 | 119.69 (19) |
C5—N2—C6 | 129.9 (2) | C16—C15—C20 | 120.47 (16) |
N1—C1—N2 | 108.0 (2) | C16—C15—B1 | 106.41 (15) |
N1—C1—C2 | 132.4 (2) | C20—C15—B1 | 133.08 (19) |
N2—C1—C2 | 119.6 (2) | C15—C16—C17 | 119.29 (16) |
C1—C2—C3 | 119.1 (3) | C15—C16—B2 | 108.31 (15) |
C1—C2—H2 | 119 (3) | C17—C16—B2 | 132.38 (19) |
C3—C2—H2 | 122 (3) | C16—C17—C18 | 120.23 (19) |
C2—C3—C4 | 120.1 (3) | C17—C18—C19 | 120.53 (16) |
C3—C4—C5 | 120.6 (4) | C18—C19—C20 | 120.01 (16) |
C3—C4—H4 | 118.3 (19) | C15—C20—C19 | 119.45 (19) |
C5—C4—H4 | 120.9 (19) | O2—B1—O4 | 122.61 (14) |
N2—C5—C4 | 119.1 (3) | O2—B1—C15 | 127.60 (16) |
N2—C6—C7 | 106.20 (19) | O4—B1—C15 | 109.78 (16) |
N1—C7—C6 | 109.5 (2) | N1—B2—C16 | 112.57 (15) |
N1—C7—C8 | 118.40 (19) | O5i—O5—C22 | 96.6 (5) |
C6—C7—C8 | 132.1 (2) | C22—C21—C22i | 86.8 (3) |
C7—C8—C9 | 122.3 (2) | O5—C22—C21 | 122.9 (4) |
C7—C8—C13 | 118.42 (19) | O5—C22—C23 | 119.5 (5) |
C9—C8—C13 | 119.2 (2) | O5—C22—H21ci | 156.26 |
C8—C9—C10 | 121.2 (2) | C21—C22—C23 | 117.6 (4) |
C9—C10—C11 | 119.3 (2) | C21—C22—H21ci | 47.89 |
O1—C11—C10 | 115.3 (2) | C23—C22—H21ci | 73.56 |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O5 | 1.083 (8) | 1.793 (11) | 2.801 (5) | 152.9 (14) |
C10—H10···O1ii | 1.084 (11) | 2.367 (14) | 3.413 (3) | 161.7 (13) |
C12—H12···C14 | 1.089 (18) | 2.49 (2) | 2.796 (6) | 94.3 (9) |
O2—H21···O4iii | 0.979 (12) | 1.728 (12) | 2.7032 (17) | 174.4 (19) |
C21—H21c···O5i | 1.08 | 1.95 | 2.331 (5) | 96.50 |
C21—H21c···C22i | 1.08 | 0.77 | 1.428 (5) | 100.27 |
C21—H21c···C23i | 1.08 | 1.47 | 2.499 (5) | 156.86 |
C22i—H21c···C21 | 0.77 | 1.08 | 1.428 (5) | 100.27 |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+3/2, −y−1/2, −z; (iii) −x+1, −y+1, −z. |
Crystal data top
C19H13B2BrN2O3 | Z = 4 |
Mr = 418.8 | F(000) = 840 |
Triclinic, P1 | Dx = 1.551 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9492 (7) Å | Cell parameters from 9881 reflections |
b = 14.5926 (12) Å | θ = 3.3–28.9° |
c = 15.0762 (12) Å | µ = 2.31 mm−1 |
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-tube | 7212 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.054 |
φ or ω oscillation scans | θmax = 32.7°, θmin = 3.0° |
Absorption correction: multi-scan Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015 | h = −13→13 |
Tmin = 0.682, Tmax = 0.746 | k = −21→21 |
72753 measured reflections | l = −21→22 |
Refinement top
Refinement on F2 | 1689 constraints |
R[F2 > 2σ(F2)] = 0.048 | All H-atom parameters refined |
wR(F2) = 0.102 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
S = 1.97 | (Δ/σ)max = 0.019 |
12047 reflections | Δρmax = 3.73 e Å−3 |
566 parameters | Δρmin = −0.79 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.72056 (3) | 0.60623 (2) | 0.181589 (19) | 0.02767 (11) | |
O1 | 0.29092 (17) | −0.03593 (12) | 0.52095 (11) | 0.0157 (6) | |
O2 | 0.43056 (16) | 0.09949 (11) | 0.51705 (11) | 0.0144 (6) | |
O3 | 0.50466 (17) | 0.26646 (12) | 0.42160 (11) | 0.0180 (6) | |
B1 | 0.2966 (3) | 0.0570 (2) | 0.51839 (18) | 0.0131 (9) | |
B2 | 0.4074 (3) | 0.2040 (2) | 0.50760 (19) | 0.0151 (10) | |
N1 | 0.4637 (2) | 0.21537 (14) | 0.59749 (13) | 0.0144 (7) | |
N2 | 0.4966 (2) | 0.19935 (15) | 0.74527 (14) | 0.0183 (8) | |
C1 | 0.4300 (3) | 0.15803 (18) | 0.69256 (17) | 0.0159 (9) | |
C2 | 0.3424 (3) | 0.07184 (19) | 0.74038 (18) | 0.0209 (9) | |
C3 | 0.3281 (3) | 0.03025 (19) | 0.83981 (18) | 0.0238 (10) | |
C4 | 0.3993 (3) | 0.0733 (2) | 0.89218 (18) | 0.0257 (10) | |
C5 | 0.4819 (3) | 0.1570 (2) | 0.84486 (18) | 0.0251 (10) | |
C6 | 0.5712 (3) | 0.28423 (18) | 0.68149 (18) | 0.0191 (9) | |
C7 | 0.5491 (3) | 0.29390 (17) | 0.59076 (17) | 0.0155 (9) | |
C8 | 0.5945 (2) | 0.36898 (17) | 0.49466 (17) | 0.0158 (9) | |
C9 | 0.6620 (3) | 0.45883 (18) | 0.48029 (18) | 0.0184 (9) | |
C10 | 0.7036 (3) | 0.52888 (19) | 0.38814 (19) | 0.0207 (9) | |
C11 | 0.6741 (3) | 0.50881 (18) | 0.30865 (17) | 0.0193 (9) | |
C12 | 0.6083 (3) | 0.42172 (19) | 0.31880 (18) | 0.0191 (9) | |
C13 | 0.5665 (2) | 0.35069 (18) | 0.41361 (17) | 0.0160 (9) | |
C14 | 0.2291 (3) | 0.22189 (17) | 0.50571 (16) | 0.0144 (8) | |
C15 | 0.1634 (2) | 0.13282 (17) | 0.51499 (16) | 0.0147 (8) | |
C16 | 0.0075 (3) | 0.12682 (19) | 0.51715 (17) | 0.0187 (9) | |
C17 | −0.0835 (3) | 0.2104 (2) | 0.50891 (19) | 0.0218 (10) | |
C18 | −0.0189 (3) | 0.2996 (2) | 0.49794 (19) | 0.0233 (10) | |
C19 | 0.1359 (3) | 0.30518 (18) | 0.49656 (17) | 0.0188 (9) | |
H1o | 0.3910 (13) | −0.0647 (18) | 0.5108 (19) | 0.014 (7)* | |
H2 | 0.297 (3) | 0.0444 (18) | 0.6925 (15) | 0.0251* | |
H3 | 0.258 (2) | −0.0351 (12) | 0.8722 (17) | 0.0285* | |
H4 | 0.382 (3) | 0.0497 (19) | 0.9704 (3) | 0.0308* | |
H5 | 0.530 (3) | 0.1992 (17) | 0.8792 (17) | 0.0302* | |
H6 | 0.633 (2) | 0.3298 (16) | 0.7056 (17) | 0.0229* | |
H9 | 0.675 (3) | 0.4769 (18) | 0.5419 (11) | 0.022* | |
H10 | 0.752 (3) | 0.5995 (9) | 0.3762 (18) | 0.0249* | |
H12 | 0.590 (3) | 0.4076 (19) | 0.2558 (11) | 0.023* | |
H16 | −0.046 (3) | 0.0585 (10) | 0.5267 (18) | 0.0225* | |
H17 | −0.2040 (6) | 0.2075 (19) | 0.5088 (18) | 0.0261* | |
H18 | −0.082 (2) | 0.3682 (10) | 0.4876 (18) | 0.028* | |
H19 | 0.184 (3) | 0.3736 (10) | 0.4914 (18) | 0.0225* | |
Br2 | 0.05274 (3) | 0.02847 (2) | 1.19386 (2) | 0.03556 (13) | |
O4 | 0.57948 (18) | 0.39765 (12) | 0.98467 (11) | 0.0187 (6) | |
O5 | 0.57061 (19) | 0.56489 (13) | 0.86603 (11) | 0.0207 (7) | |
O6 | 0.53723 (19) | 0.22455 (13) | 1.01301 (11) | 0.0221 (7) | |
B3 | 0.6188 (3) | 0.4688 (2) | 0.89453 (19) | 0.0180 (10) | |
B4 | 0.6508 (3) | 0.2996 (2) | 0.99513 (19) | 0.0194 (10) | |
N3 | 0.7316 (2) | 0.26363 (15) | 1.09036 (13) | 0.0175 (7) | |
N4 | 0.8717 (2) | 0.25682 (16) | 1.20356 (14) | 0.0214 (8) | |
C20 | 0.8641 (3) | 0.29243 (18) | 1.10489 (17) | 0.0196 (9) | |
C21 | 0.9840 (3) | 0.3482 (2) | 1.04002 (18) | 0.0255 (10) | |
C22 | 1.1066 (3) | 0.3642 (2) | 1.0781 (2) | 0.0282 (11) | |
C23 | 1.1118 (3) | 0.3258 (2) | 1.17989 (19) | 0.0284 (11) | |
C24 | 0.9947 (3) | 0.2724 (2) | 1.24092 (18) | 0.0254 (10) | |
C25 | 0.7411 (3) | 0.20622 (19) | 1.25110 (17) | 0.0215 (9) | |
C26 | 0.6545 (3) | 0.21151 (18) | 1.18055 (16) | 0.0184 (9) | |
C27 | 0.5082 (3) | 0.17192 (18) | 1.18682 (17) | 0.0196 (9) | |
C28 | 0.4222 (3) | 0.1206 (2) | 1.27462 (18) | 0.0260 (10) | |
C29 | 0.2861 (3) | 0.0768 (2) | 1.27880 (19) | 0.0294 (11) | |
C30 | 0.2373 (3) | 0.0870 (2) | 1.19143 (19) | 0.0249 (10) | |
C31 | 0.3169 (3) | 0.13956 (19) | 1.10202 (18) | 0.0222 (10) | |
C32 | 0.4552 (3) | 0.18086 (18) | 1.09940 (17) | 0.0189 (9) | |
C33 | 0.7538 (3) | 0.32250 (18) | 0.89358 (17) | 0.0189 (9) | |
C34 | 0.7302 (3) | 0.42263 (19) | 0.83309 (16) | 0.0186 (9) | |
C35 | 0.8027 (3) | 0.4626 (2) | 0.73856 (17) | 0.0214 (10) | |
C36 | 0.8994 (3) | 0.4013 (2) | 0.70402 (19) | 0.0276 (11) | |
C37 | 0.9228 (3) | 0.3024 (2) | 0.7628 (2) | 0.0274 (11) | |
C38 | 0.8509 (3) | 0.2619 (2) | 0.85778 (19) | 0.0249 (10) | |
H21 | 0.973 (3) | 0.3798 (18) | 0.9630 (5) | 0.0306* | |
H22 | 1.198 (2) | 0.4066 (17) | 1.0275 (15) | 0.0338* | |
H23 | 1.2101 (18) | 0.337 (2) | 1.2091 (18) | 0.0341* | |
H24 | 0.977 (3) | 0.2404 (18) | 1.3196 (2) | 0.0305* | |
H28 | 0.462 (3) | 0.114 (2) | 1.3420 (10) | 0.0313* | |
H29 | 0.221 (3) | 0.0267 (16) | 1.3436 (11) | 0.0353* | |
H31 | 0.263 (3) | 0.1440 (19) | 1.0401 (11) | 0.0266* | |
H35 | 0.777 (3) | 0.5393 (6) | 0.6936 (15) | 0.0256* | |
H36 | 0.953 (3) | 0.4371 (18) | 0.6304 (7) | 0.0331* | |
H37 | 0.994 (2) | 0.2517 (16) | 0.7389 (19) | 0.0329* | |
H38 | 0.880 (3) | 0.1857 (7) | 0.9023 (16) | 0.0299* | |
H20 | 0.505 (3) | 0.579 (2) | 0.9171 (16) | 0.031* | |
H5o | 0.716 (3) | 0.1764 (18) | 1.3294 (3) | 0.0259* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.03108 (16) | 0.02376 (15) | 0.02174 (14) | −0.00886 (12) | 0.00000 (11) | −0.00167 (11) |
O1 | 0.0135 (8) | 0.0173 (9) | 0.0181 (8) | −0.0007 (7) | −0.0029 (7) | −0.0083 (7) |
O2 | 0.0114 (8) | 0.0174 (9) | 0.0170 (8) | −0.0004 (6) | −0.0018 (6) | −0.0093 (7) |
O3 | 0.0184 (9) | 0.0211 (9) | 0.0171 (8) | −0.0044 (7) | 0.0006 (7) | −0.0103 (7) |
B1 | 0.0187 (13) | 0.0153 (14) | 0.0062 (12) | −0.0007 (11) | −0.0005 (10) | −0.0053 (10) |
B2 | 0.0151 (13) | 0.0187 (14) | 0.0139 (13) | 0.0001 (11) | −0.0031 (10) | −0.0084 (11) |
N1 | 0.0128 (10) | 0.0157 (10) | 0.0168 (10) | −0.0010 (8) | −0.0019 (8) | −0.0084 (8) |
N2 | 0.0221 (11) | 0.0183 (11) | 0.0184 (10) | 0.0004 (9) | −0.0079 (8) | −0.0096 (9) |
C1 | 0.0173 (12) | 0.0166 (12) | 0.0169 (12) | −0.0021 (10) | −0.0052 (9) | −0.0084 (10) |
C2 | 0.0264 (14) | 0.0203 (13) | 0.0163 (13) | −0.0074 (11) | −0.0021 (10) | −0.0065 (11) |
C3 | 0.0296 (14) | 0.0217 (14) | 0.0190 (13) | −0.0015 (11) | −0.0014 (11) | −0.0070 (11) |
C4 | 0.0360 (16) | 0.0257 (15) | 0.0164 (13) | 0.0000 (12) | −0.0061 (11) | −0.0085 (12) |
C5 | 0.0369 (16) | 0.0242 (15) | 0.0175 (13) | −0.0022 (12) | −0.0103 (11) | −0.0090 (11) |
C6 | 0.0223 (13) | 0.0195 (13) | 0.0207 (13) | −0.0015 (10) | −0.0082 (10) | −0.0115 (11) |
C7 | 0.0127 (11) | 0.0142 (12) | 0.0198 (12) | 0.0014 (9) | −0.0019 (9) | −0.0070 (10) |
C8 | 0.0148 (11) | 0.0146 (12) | 0.0198 (12) | −0.0014 (9) | −0.0036 (9) | −0.0078 (10) |
C9 | 0.0185 (12) | 0.0152 (13) | 0.0237 (13) | −0.0026 (10) | −0.0040 (10) | −0.0092 (11) |
C10 | 0.0201 (13) | 0.0161 (13) | 0.0247 (14) | −0.0033 (10) | −0.0029 (10) | −0.0059 (11) |
C11 | 0.0150 (12) | 0.0184 (13) | 0.0214 (13) | −0.0030 (10) | −0.0002 (10) | −0.0048 (10) |
C12 | 0.0180 (12) | 0.0201 (13) | 0.0178 (13) | −0.0037 (10) | −0.0003 (10) | −0.0058 (11) |
C13 | 0.0140 (11) | 0.0176 (12) | 0.0165 (12) | −0.0014 (9) | −0.0013 (9) | −0.0069 (10) |
C14 | 0.0157 (12) | 0.0151 (12) | 0.0136 (11) | −0.0018 (9) | −0.0019 (9) | −0.0066 (9) |
C15 | 0.0128 (11) | 0.0166 (12) | 0.0146 (11) | −0.0013 (9) | −0.0042 (9) | −0.0052 (10) |
C16 | 0.0124 (12) | 0.0225 (14) | 0.0235 (13) | −0.0018 (10) | −0.0012 (10) | −0.0114 (11) |
C17 | 0.0128 (12) | 0.0240 (14) | 0.0332 (14) | 0.0047 (11) | −0.0048 (11) | −0.0162 (12) |
C18 | 0.0164 (13) | 0.0248 (15) | 0.0321 (14) | 0.0058 (11) | −0.0053 (11) | −0.0148 (12) |
C19 | 0.0197 (13) | 0.0159 (13) | 0.0232 (13) | 0.0016 (10) | −0.0052 (10) | −0.0097 (11) |
Br2 | 0.02619 (16) | 0.0470 (2) | 0.03340 (17) | −0.01478 (13) | −0.00007 (12) | −0.01435 (15) |
O4 | 0.0237 (9) | 0.0206 (9) | 0.0098 (8) | −0.0033 (7) | 0.0002 (7) | −0.0040 (7) |
O5 | 0.0243 (10) | 0.0216 (10) | 0.0138 (9) | −0.0021 (8) | −0.0015 (7) | −0.0044 (7) |
O6 | 0.0296 (10) | 0.0273 (10) | 0.0113 (8) | −0.0077 (8) | −0.0002 (7) | −0.0089 (7) |
B3 | 0.0173 (14) | 0.0233 (16) | 0.0160 (13) | −0.0040 (12) | −0.0062 (11) | −0.0084 (12) |
B4 | 0.0221 (15) | 0.0255 (16) | 0.0121 (13) | −0.0036 (12) | −0.0014 (11) | −0.0086 (12) |
N3 | 0.0219 (11) | 0.0168 (11) | 0.0129 (10) | −0.0015 (8) | 0.0001 (8) | −0.0052 (8) |
N4 | 0.0289 (12) | 0.0231 (12) | 0.0122 (10) | −0.0030 (9) | −0.0029 (9) | −0.0062 (9) |
C20 | 0.0256 (14) | 0.0201 (13) | 0.0117 (12) | −0.0048 (11) | −0.0007 (10) | −0.0045 (10) |
C21 | 0.0287 (15) | 0.0292 (15) | 0.0158 (13) | −0.0102 (12) | −0.0006 (11) | −0.0049 (11) |
C22 | 0.0288 (15) | 0.0333 (16) | 0.0230 (14) | −0.0121 (12) | −0.0032 (11) | −0.0096 (12) |
C23 | 0.0308 (15) | 0.0345 (16) | 0.0211 (14) | −0.0087 (13) | −0.0068 (12) | −0.0097 (12) |
C24 | 0.0301 (15) | 0.0298 (15) | 0.0162 (13) | −0.0058 (12) | −0.0052 (11) | −0.0072 (12) |
C25 | 0.0280 (14) | 0.0268 (14) | 0.0080 (11) | −0.0035 (11) | −0.0016 (10) | −0.0045 (11) |
C26 | 0.0218 (13) | 0.0165 (13) | 0.0167 (12) | −0.0016 (10) | 0.0008 (10) | −0.0069 (10) |
C27 | 0.0253 (13) | 0.0209 (13) | 0.0114 (12) | −0.0006 (10) | −0.0011 (10) | −0.0053 (10) |
C28 | 0.0241 (14) | 0.0360 (16) | 0.0136 (13) | −0.0055 (12) | 0.0004 (11) | −0.0049 (12) |
C29 | 0.0258 (15) | 0.0400 (17) | 0.0180 (14) | −0.0094 (12) | −0.0006 (11) | −0.0057 (12) |
C30 | 0.0247 (14) | 0.0287 (15) | 0.0207 (14) | −0.0046 (12) | 0.0009 (11) | −0.0094 (12) |
C31 | 0.0244 (14) | 0.0237 (14) | 0.0190 (13) | −0.0044 (11) | −0.0012 (11) | −0.0088 (11) |
C32 | 0.0216 (13) | 0.0193 (13) | 0.0156 (12) | −0.0021 (10) | −0.0001 (10) | −0.0071 (10) |
C33 | 0.0229 (13) | 0.0216 (14) | 0.0144 (12) | −0.0033 (11) | −0.0015 (10) | −0.0090 (11) |
C34 | 0.0220 (13) | 0.0231 (14) | 0.0101 (11) | −0.0069 (10) | −0.0018 (9) | −0.0049 (10) |
C35 | 0.0212 (13) | 0.0278 (15) | 0.0140 (12) | −0.0042 (11) | 0.0029 (10) | −0.0080 (11) |
C36 | 0.0259 (14) | 0.0404 (18) | 0.0175 (13) | −0.0074 (13) | 0.0026 (11) | −0.0129 (13) |
C37 | 0.0237 (14) | 0.0390 (18) | 0.0237 (14) | 0.0008 (12) | 0.0012 (11) | −0.0182 (13) |
C38 | 0.0275 (14) | 0.0305 (16) | 0.0188 (14) | 0.0014 (12) | −0.0020 (11) | −0.0124 (12) |
Geometric parameters (Å, º) top
Br1—C11 | 1.894 (2) | Br2—C30 | 1.899 (3) |
O1—B1 | 1.345 (4) | O4—B3 | 1.364 (3) |
O2—B1 | 1.381 (3) | O5—B3 | 1.353 (3) |
O3—C13 | 1.336 (3) | O6—C32 | 1.341 (3) |
B1—C15 | 1.563 (4) | B3—C34 | 1.571 (4) |
B2—N1 | 1.577 (4) | B4—N3 | 1.578 (3) |
B2—C14 | 1.602 (4) | B4—C33 | 1.603 (4) |
N1—C1 | 1.350 (3) | N3—C20 | 1.355 (4) |
N1—C7 | 1.382 (4) | N3—C26 | 1.383 (3) |
N2—C1 | 1.379 (4) | N4—C20 | 1.379 (3) |
N2—C5 | 1.372 (3) | N4—C24 | 1.370 (4) |
N2—C6 | 1.380 (3) | N4—C25 | 1.379 (3) |
C1—C2 | 1.409 (4) | C20—C21 | 1.409 (3) |
C2—C3 | 1.369 (4) | C21—C22 | 1.376 (4) |
C3—C4 | 1.414 (5) | C22—C23 | 1.417 (4) |
C4—C5 | 1.357 (4) | C23—C24 | 1.357 (3) |
C6—C7 | 1.358 (5) | C25—C26 | 1.371 (4) |
C7—C8 | 1.455 (3) | C26—C27 | 1.443 (4) |
C8—C9 | 1.405 (4) | C27—C28 | 1.390 (3) |
C8—C13 | 1.406 (5) | C27—C32 | 1.413 (5) |
C9—C10 | 1.382 (3) | C28—C29 | 1.395 (4) |
C10—C11 | 1.399 (5) | C29—C30 | 1.392 (5) |
C11—C12 | 1.381 (4) | C30—C31 | 1.385 (3) |
C12—C13 | 1.414 (3) | C31—C32 | 1.401 (4) |
C14—C15 | 1.411 (4) | C33—C34 | 1.403 (3) |
C14—C19 | 1.399 (4) | C33—C38 | 1.407 (4) |
C15—C16 | 1.399 (3) | C34—C35 | 1.394 (4) |
C16—C17 | 1.394 (4) | C35—C36 | 1.403 (4) |
C17—C18 | 1.400 (4) | C36—C37 | 1.383 (3) |
C18—C19 | 1.390 (4) | C37—C38 | 1.399 (4) |
| | | |
O1—B1—O2 | 122.1 (2) | O4—B3—O5 | 123.6 (2) |
O1—B1—C15 | 128.1 (2) | O4—B3—C34 | 109.8 (2) |
O2—B1—C15 | 109.8 (2) | O5—B3—C34 | 126.6 (2) |
N1—B2—C14 | 112.2 (2) | N3—B4—C33 | 118.0 (2) |
B2—N1—C1 | 127.9 (2) | B4—N3—C20 | 129.71 (16) |
B2—N1—C7 | 124.03 (17) | B4—N3—C26 | 121.1 (2) |
C1—N1—C7 | 107.8 (2) | C20—N3—C26 | 107.6 (2) |
C1—N2—C5 | 121.15 (19) | C20—N4—C24 | 121.8 (2) |
C1—N2—C6 | 108.7 (2) | C20—N4—C25 | 108.6 (2) |
C5—N2—C6 | 130.2 (2) | C24—N4—C25 | 129.66 (19) |
N1—C1—N2 | 107.8 (2) | N3—C20—N4 | 108.20 (19) |
N1—C1—C2 | 131.8 (3) | N3—C20—C21 | 132.2 (3) |
N2—C1—C2 | 120.4 (2) | N4—C20—C21 | 119.6 (3) |
C1—C2—C3 | 117.9 (3) | C20—C21—C22 | 118.2 (3) |
C2—C3—C4 | 120.6 (2) | C21—C22—C23 | 120.9 (2) |
C3—C4—C5 | 120.6 (3) | C22—C23—C24 | 119.8 (3) |
N2—C5—C4 | 119.3 (3) | N4—C24—C23 | 119.7 (3) |
N2—C6—C7 | 106.5 (3) | N4—C25—C26 | 106.6 (2) |
N1—C7—C6 | 109.2 (2) | N3—C26—C25 | 109.0 (2) |
N1—C7—C8 | 118.2 (3) | N3—C26—C27 | 119.5 (3) |
C6—C7—C8 | 132.6 (3) | C25—C26—C27 | 131.5 (2) |
C7—C8—C9 | 122.8 (3) | C26—C27—C28 | 123.0 (3) |
C7—C8—C13 | 117.9 (3) | C26—C27—C32 | 117.9 (2) |
C9—C8—C13 | 119.3 (2) | C28—C27—C32 | 119.0 (3) |
C8—C9—C10 | 121.5 (3) | C27—C28—C29 | 121.8 (3) |
C9—C10—C11 | 118.0 (3) | C28—C29—C30 | 117.7 (2) |
Br1—C11—C10 | 119.0 (2) | Br2—C30—C29 | 119.04 (18) |
Br1—C11—C12 | 118.1 (2) | Br2—C30—C31 | 118.3 (2) |
C10—C11—C12 | 122.9 (2) | C29—C30—C31 | 122.7 (3) |
C11—C12—C13 | 118.4 (3) | C30—C31—C32 | 118.8 (3) |
O3—C13—C8 | 122.7 (2) | O6—C32—C27 | 121.6 (2) |
O3—C13—C12 | 117.4 (3) | O6—C32—C31 | 118.3 (3) |
C8—C13—C12 | 119.9 (3) | C27—C32—C31 | 120.0 (2) |
B2—C14—C15 | 108.7 (2) | B4—C33—C34 | 108.2 (2) |
B2—C14—C19 | 132.5 (3) | B4—C33—C38 | 132.3 (2) |
C15—C14—C19 | 118.8 (2) | C34—C33—C38 | 119.4 (2) |
B1—C15—C14 | 106.20 (19) | B3—C34—C33 | 106.6 (2) |
B1—C15—C16 | 132.9 (3) | B3—C34—C35 | 132.6 (2) |
C14—C15—C16 | 120.8 (2) | C33—C34—C35 | 120.8 (3) |
C15—C16—C17 | 119.4 (3) | C34—C35—C36 | 119.2 (2) |
C16—C17—C18 | 120.1 (3) | C35—C36—C37 | 120.5 (2) |
C17—C18—C19 | 120.4 (3) | C36—C37—C38 | 120.6 (3) |
C14—C19—C18 | 120.4 (3) | C33—C38—C37 | 119.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···O2i | 0.985 (16) | 1.693 (15) | 2.672 (2) | 172 (2) |
C5—H5···O6 | 1.08 (4) | 2.20 (3) | 3.163 (4) | 146.7 (18) |
C12—H12···O5ii | 1.08 (2) | 2.38 (2) | 3.326 (4) | 146 (2) |
C16—H16···O1iii | 1.08 (2) | 2.48 (3) | 3.270 (4) | 129.5 (15) |
C23—H23···O5iv | 1.08 (3) | 2.39 (2) | 3.212 (3) | 132.0 (18) |
O5—H20···O4v | 0.98 (3) | 1.72 (3) | 2.692 (2) | 169 (3) |
C25—H5o···O1vi | 1.082 (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. |