Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701450X/at2245sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680701450X/at2245Isup2.hkl |
CCDC reference: 646698
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.
C17H13Br2Cl2NO5 | F(000) = 4256 |
Mr = 542.00 | Dx = 1.863 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 71102 reflections |
a = 13.7847 (4) Å | θ = 1.9–26.7° |
b = 18.7740 (5) Å | µ = 4.50 mm−1 |
c = 29.8756 (10) Å | T = 173 K |
V = 7731.6 (4) Å3 | Block, light yellow |
Z = 16 | 0.35 × 0.32 × 0.22 mm |
Stoe IPDSII two-circle diffractometer | 7902 independent reflections |
Radiation source: fine-focus sealed tube | 6553 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.090 |
ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −17→17 |
Tmin = 0.232, Tmax = 0.388 | k = −23→23 |
114175 measured reflections | l = −37→37 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.053P)2 + 5.2549P] where P = (Fo2 + 2Fc2)/3 |
7902 reflections | (Δ/σ)max = 0.002 |
491 parameters | Δρmax = 1.05 e Å−3 |
0 restraints | Δρmin = −0.99 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.34736 (3) | 0.19494 (2) | 0.296868 (16) | 0.04086 (11) | |
Br2 | 0.01843 (3) | 0.23847 (2) | 0.313699 (12) | 0.02994 (9) | |
Cl1 | 0.10217 (8) | 0.45244 (5) | 0.35599 (3) | 0.0380 (2) | |
Cl2 | 0.11140 (7) | 0.57268 (5) | 0.19429 (3) | 0.0362 (2) | |
N1 | 0.1804 (2) | 0.07933 (16) | 0.39276 (10) | 0.0296 (7) | |
O1 | 0.2526 (2) | 0.11462 (16) | 0.40227 (9) | 0.0459 (8) | |
O2 | 0.1238 (2) | 0.05664 (17) | 0.42084 (9) | 0.0446 (7) | |
O3 | 0.22854 (19) | 0.32542 (12) | 0.34546 (8) | 0.0278 (5) | |
C1 | 0.2126 (3) | 0.18511 (18) | 0.31910 (11) | 0.0250 (7) | |
H1 | 0.2117 | 0.1953 | 0.3520 | 0.030* | |
C2 | 0.1559 (3) | 0.24322 (18) | 0.29489 (11) | 0.0252 (7) | |
H2 | 0.1620 | 0.2380 | 0.2617 | 0.030* | |
C3 | 0.1864 (3) | 0.31773 (17) | 0.30990 (11) | 0.0230 (7) | |
C11 | 0.1786 (2) | 0.11002 (18) | 0.31160 (11) | 0.0239 (7) | |
C12 | 0.1626 (2) | 0.06121 (18) | 0.34556 (11) | 0.0231 (7) | |
C13 | 0.1279 (2) | −0.00729 (18) | 0.33788 (11) | 0.0236 (7) | |
H13 | 0.1149 | −0.0381 | 0.3624 | 0.028* | |
C14 | 0.1126 (2) | −0.03034 (17) | 0.29470 (11) | 0.0226 (7) | |
C15 | 0.1286 (2) | 0.01807 (17) | 0.25876 (11) | 0.0218 (6) | |
C16 | 0.1604 (3) | 0.08630 (18) | 0.26790 (11) | 0.0242 (7) | |
H16 | 0.1703 | 0.1183 | 0.2437 | 0.029* | |
O17 | 0.08269 (19) | −0.09633 (12) | 0.28302 (8) | 0.0283 (5) | |
C17 | 0.0329 (3) | −0.13690 (19) | 0.31647 (14) | 0.0334 (8) | |
H17A | 0.0797 | −0.1543 | 0.3386 | 0.050* | |
H17B | 0.0003 | −0.1775 | 0.3024 | 0.050* | |
H17C | −0.0152 | −0.1067 | 0.3313 | 0.050* | |
O18 | 0.11068 (18) | −0.00839 (13) | 0.21769 (8) | 0.0269 (5) | |
C18 | 0.1171 (3) | 0.0399 (2) | 0.18053 (11) | 0.0296 (8) | |
H18A | 0.0712 | 0.0792 | 0.1848 | 0.044* | |
H18B | 0.1013 | 0.0145 | 0.1528 | 0.044* | |
H18C | 0.1831 | 0.0589 | 0.1786 | 0.044* | |
C21 | 0.1602 (2) | 0.37956 (17) | 0.28114 (11) | 0.0210 (6) | |
C22 | 0.1284 (3) | 0.44415 (18) | 0.29944 (10) | 0.0225 (7) | |
C23 | 0.1131 (2) | 0.50301 (18) | 0.27275 (11) | 0.0256 (7) | |
H23 | 0.0919 | 0.5467 | 0.2855 | 0.031* | |
C24 | 0.1291 (3) | 0.49745 (19) | 0.22715 (12) | 0.0266 (7) | |
C25 | 0.1592 (3) | 0.4345 (2) | 0.20787 (12) | 0.0298 (8) | |
H25 | 0.1697 | 0.4315 | 0.1765 | 0.036* | |
C26 | 0.1740 (3) | 0.37549 (19) | 0.23502 (11) | 0.0275 (7) | |
H26 | 0.1938 | 0.3317 | 0.2220 | 0.033* | |
Br1A | 0.12798 (3) | 0.62092 (2) | 0.537826 (15) | 0.03877 (11) | |
Br2A | 0.45220 (3) | 0.56514 (2) | 0.556602 (15) | 0.03595 (10) | |
Cl1A | 0.39209 (7) | 0.36144 (5) | 0.59140 (3) | 0.0327 (2) | |
Cl2A | 0.37804 (7) | 0.25580 (5) | 0.42570 (3) | 0.0343 (2) | |
N1A | 0.2714 (3) | 0.73618 (17) | 0.63575 (10) | 0.0441 (9) | |
O1A | 0.3063 (4) | 0.7664 (2) | 0.66765 (10) | 0.0813 (15) | |
O2A | 0.1971 (3) | 0.69909 (16) | 0.63830 (10) | 0.0475 (8) | |
O3A | 0.24269 (18) | 0.48270 (13) | 0.59001 (8) | 0.0275 (5) | |
C1A | 0.2613 (3) | 0.62491 (19) | 0.56295 (12) | 0.0297 (8) | |
H1A | 0.2588 | 0.6133 | 0.5956 | 0.036* | |
C2A | 0.3130 (3) | 0.56613 (18) | 0.53875 (11) | 0.0263 (7) | |
H2A | 0.3063 | 0.5718 | 0.5056 | 0.032* | |
C3A | 0.2797 (2) | 0.49174 (17) | 0.55358 (11) | 0.0233 (7) | |
C11A | 0.3042 (3) | 0.69838 (18) | 0.55698 (11) | 0.0260 (7) | |
C12A | 0.3151 (3) | 0.74758 (18) | 0.59164 (11) | 0.0276 (7) | |
C13A | 0.3643 (3) | 0.81213 (18) | 0.58631 (11) | 0.0265 (7) | |
H13A | 0.3724 | 0.8433 | 0.6111 | 0.032* | |
C14A | 0.4011 (2) | 0.83043 (18) | 0.54508 (11) | 0.0236 (7) | |
C15A | 0.3866 (2) | 0.78340 (17) | 0.50860 (10) | 0.0215 (7) | |
C16A | 0.3405 (3) | 0.71866 (17) | 0.51515 (11) | 0.0228 (7) | |
H16A | 0.3334 | 0.6871 | 0.4905 | 0.027* | |
O17A | 0.44972 (19) | 0.89104 (13) | 0.53532 (8) | 0.0308 (6) | |
C17A | 0.4874 (3) | 0.9313 (2) | 0.57219 (14) | 0.0356 (9) | |
H17D | 0.4335 | 0.9505 | 0.5899 | 0.053* | |
H17E | 0.5271 | 0.9707 | 0.5608 | 0.053* | |
H17F | 0.5274 | 0.9003 | 0.5911 | 0.053* | |
O18A | 0.42239 (18) | 0.80665 (13) | 0.46941 (7) | 0.0268 (5) | |
C18A | 0.4059 (3) | 0.7646 (2) | 0.43021 (11) | 0.0305 (8) | |
H18D | 0.4329 | 0.7168 | 0.4347 | 0.046* | |
H18E | 0.4375 | 0.7871 | 0.4045 | 0.046* | |
H18F | 0.3360 | 0.7609 | 0.4246 | 0.046* | |
C21A | 0.3037 (2) | 0.43203 (17) | 0.52252 (11) | 0.0224 (7) | |
C22A | 0.3530 (2) | 0.37080 (18) | 0.53647 (11) | 0.0236 (7) | |
C23A | 0.3761 (2) | 0.31665 (18) | 0.50703 (12) | 0.0245 (7) | |
H23A | 0.4111 | 0.2759 | 0.5169 | 0.029* | |
C24A | 0.3470 (2) | 0.32315 (18) | 0.46278 (12) | 0.0249 (7) | |
C25A | 0.2953 (3) | 0.38161 (18) | 0.44777 (11) | 0.0248 (7) | |
H25A | 0.2742 | 0.3846 | 0.4176 | 0.030* | |
C26A | 0.2752 (2) | 0.43563 (17) | 0.47785 (11) | 0.0234 (7) | |
H26A | 0.2408 | 0.4764 | 0.4677 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0312 (2) | 0.02526 (19) | 0.0661 (3) | −0.00365 (15) | 0.00757 (18) | −0.01044 (18) |
Br2 | 0.02930 (19) | 0.03270 (19) | 0.02783 (18) | −0.00184 (14) | −0.00275 (14) | −0.00038 (14) |
Cl1 | 0.0597 (6) | 0.0335 (5) | 0.0208 (4) | 0.0133 (4) | 0.0087 (4) | −0.0026 (3) |
Cl2 | 0.0432 (5) | 0.0306 (5) | 0.0347 (5) | 0.0008 (4) | −0.0001 (4) | 0.0133 (4) |
N1 | 0.0400 (18) | 0.0248 (15) | 0.0240 (15) | 0.0009 (13) | −0.0073 (13) | 0.0010 (12) |
O1 | 0.060 (2) | 0.0438 (17) | 0.0339 (15) | −0.0172 (15) | −0.0208 (14) | 0.0021 (13) |
O2 | 0.0561 (19) | 0.0536 (18) | 0.0241 (14) | −0.0054 (15) | 0.0038 (13) | 0.0036 (13) |
O3 | 0.0419 (15) | 0.0226 (12) | 0.0189 (11) | 0.0014 (10) | −0.0084 (10) | −0.0031 (9) |
C1 | 0.0294 (18) | 0.0222 (17) | 0.0234 (17) | −0.0010 (13) | −0.0018 (14) | −0.0015 (13) |
C2 | 0.0349 (19) | 0.0230 (17) | 0.0179 (15) | −0.0002 (14) | 0.0002 (13) | 0.0015 (13) |
C3 | 0.0285 (17) | 0.0206 (16) | 0.0199 (16) | 0.0018 (13) | 0.0048 (13) | −0.0010 (13) |
C11 | 0.0267 (17) | 0.0204 (16) | 0.0247 (17) | 0.0013 (13) | −0.0022 (14) | −0.0004 (13) |
C12 | 0.0261 (17) | 0.0228 (16) | 0.0206 (16) | 0.0009 (13) | −0.0050 (13) | 0.0012 (13) |
C13 | 0.0241 (16) | 0.0231 (16) | 0.0235 (16) | 0.0017 (13) | −0.0023 (13) | 0.0059 (13) |
C14 | 0.0225 (17) | 0.0170 (15) | 0.0284 (17) | −0.0009 (12) | −0.0039 (13) | 0.0002 (13) |
C15 | 0.0228 (16) | 0.0225 (16) | 0.0202 (16) | 0.0007 (13) | −0.0017 (12) | −0.0010 (12) |
C16 | 0.0293 (18) | 0.0213 (16) | 0.0220 (16) | −0.0014 (13) | −0.0008 (13) | 0.0027 (13) |
O17 | 0.0355 (14) | 0.0182 (11) | 0.0314 (13) | −0.0056 (10) | −0.0038 (11) | 0.0002 (10) |
C17 | 0.036 (2) | 0.0199 (17) | 0.044 (2) | −0.0023 (15) | 0.0026 (17) | 0.0066 (16) |
O18 | 0.0349 (14) | 0.0253 (12) | 0.0204 (11) | −0.0057 (10) | −0.0038 (10) | −0.0023 (9) |
C18 | 0.039 (2) | 0.0295 (18) | 0.0201 (17) | −0.0061 (15) | 0.0011 (15) | 0.0034 (14) |
C21 | 0.0241 (16) | 0.0215 (16) | 0.0175 (15) | −0.0012 (13) | −0.0015 (12) | −0.0016 (12) |
C22 | 0.0275 (17) | 0.0225 (16) | 0.0174 (15) | 0.0001 (13) | 0.0022 (13) | −0.0023 (12) |
C23 | 0.0282 (18) | 0.0215 (16) | 0.0270 (17) | 0.0016 (13) | −0.0002 (14) | −0.0003 (13) |
C24 | 0.0269 (17) | 0.0250 (17) | 0.0277 (18) | −0.0015 (14) | −0.0028 (14) | 0.0068 (14) |
C25 | 0.039 (2) | 0.0311 (19) | 0.0191 (17) | −0.0030 (15) | 0.0015 (14) | −0.0001 (14) |
C26 | 0.038 (2) | 0.0229 (17) | 0.0218 (16) | −0.0015 (14) | 0.0012 (14) | −0.0034 (13) |
Br1A | 0.02470 (19) | 0.0303 (2) | 0.0613 (3) | −0.00031 (14) | −0.00662 (17) | 0.01230 (18) |
Br2A | 0.02294 (18) | 0.02966 (19) | 0.0553 (2) | 0.00009 (14) | −0.00315 (16) | 0.00539 (17) |
Cl1A | 0.0460 (5) | 0.0298 (4) | 0.0223 (4) | 0.0067 (4) | −0.0081 (4) | −0.0002 (3) |
Cl2A | 0.0418 (5) | 0.0302 (4) | 0.0308 (4) | 0.0057 (4) | −0.0046 (4) | −0.0105 (4) |
N1A | 0.085 (3) | 0.0258 (17) | 0.0211 (16) | −0.0067 (18) | 0.0103 (17) | −0.0013 (13) |
O1A | 0.157 (4) | 0.069 (2) | 0.0177 (15) | −0.046 (3) | 0.007 (2) | −0.0095 (15) |
O2A | 0.069 (2) | 0.0361 (16) | 0.0377 (16) | −0.0077 (15) | 0.0219 (15) | 0.0009 (13) |
O3A | 0.0337 (14) | 0.0269 (12) | 0.0220 (12) | 0.0022 (10) | 0.0037 (10) | 0.0011 (10) |
C1A | 0.037 (2) | 0.0265 (18) | 0.0253 (17) | 0.0006 (15) | 0.0017 (15) | 0.0010 (14) |
C2A | 0.0347 (19) | 0.0226 (17) | 0.0217 (16) | −0.0011 (14) | −0.0019 (14) | −0.0010 (13) |
C3A | 0.0260 (17) | 0.0205 (16) | 0.0233 (17) | 0.0011 (13) | −0.0034 (13) | 0.0001 (13) |
C11A | 0.039 (2) | 0.0187 (16) | 0.0203 (16) | 0.0018 (14) | −0.0018 (14) | −0.0012 (13) |
C12A | 0.043 (2) | 0.0234 (17) | 0.0164 (15) | 0.0016 (15) | 0.0004 (15) | −0.0008 (13) |
C13A | 0.0360 (19) | 0.0228 (17) | 0.0207 (16) | −0.0001 (14) | −0.0027 (14) | −0.0045 (13) |
C14A | 0.0228 (16) | 0.0237 (16) | 0.0243 (16) | −0.0014 (13) | −0.0024 (13) | −0.0033 (13) |
C15A | 0.0224 (16) | 0.0237 (16) | 0.0184 (15) | 0.0018 (13) | −0.0003 (12) | −0.0016 (12) |
C16A | 0.0309 (18) | 0.0198 (15) | 0.0178 (15) | 0.0011 (13) | −0.0011 (13) | −0.0047 (12) |
O17A | 0.0352 (14) | 0.0292 (13) | 0.0281 (13) | −0.0133 (11) | 0.0026 (11) | −0.0069 (10) |
C17A | 0.037 (2) | 0.0305 (19) | 0.040 (2) | −0.0077 (16) | −0.0056 (17) | −0.0124 (17) |
O18A | 0.0322 (13) | 0.0306 (13) | 0.0174 (11) | −0.0066 (10) | 0.0039 (9) | −0.0029 (10) |
C18A | 0.036 (2) | 0.039 (2) | 0.0162 (16) | −0.0006 (16) | −0.0010 (14) | −0.0056 (15) |
C21A | 0.0241 (16) | 0.0206 (16) | 0.0226 (16) | −0.0035 (13) | −0.0005 (13) | −0.0003 (13) |
C22A | 0.0263 (17) | 0.0207 (16) | 0.0239 (17) | −0.0034 (13) | −0.0025 (13) | −0.0002 (13) |
C23A | 0.0228 (16) | 0.0207 (16) | 0.0299 (18) | −0.0011 (13) | −0.0036 (13) | −0.0010 (13) |
C24A | 0.0265 (17) | 0.0221 (16) | 0.0260 (17) | −0.0032 (13) | 0.0001 (14) | −0.0077 (13) |
C25A | 0.0289 (18) | 0.0239 (17) | 0.0215 (16) | −0.0054 (13) | −0.0041 (13) | −0.0005 (13) |
C26A | 0.0261 (17) | 0.0195 (15) | 0.0246 (16) | −0.0008 (13) | −0.0024 (13) | 0.0037 (13) |
Br1—C1 | 1.982 (4) | Br1A—C1A | 1.987 (4) |
Br2—C2 | 1.979 (4) | Br2A—C2A | 1.992 (4) |
Cl1—C22 | 1.735 (3) | Cl1A—C22A | 1.736 (3) |
Cl2—C24 | 1.737 (3) | Cl2A—C24A | 1.735 (3) |
N1—O2 | 1.222 (4) | N1A—O1A | 1.209 (5) |
N1—O1 | 1.229 (4) | N1A—O2A | 1.242 (5) |
N1—C12 | 1.471 (4) | N1A—C12A | 1.464 (5) |
O3—C3 | 1.220 (4) | O3A—C3A | 1.214 (4) |
C1—C11 | 1.502 (5) | C1A—C2A | 1.499 (5) |
C1—C2 | 1.524 (5) | C1A—C11A | 1.511 (5) |
C1—H1 | 1.0000 | C1A—H1A | 1.0000 |
C2—C3 | 1.528 (5) | C2A—C3A | 1.535 (5) |
C2—H2 | 1.0000 | C2A—H2A | 1.0000 |
C3—C21 | 1.489 (5) | C3A—C21A | 1.493 (5) |
C11—C12 | 1.385 (5) | C11A—C12A | 1.396 (5) |
C11—C16 | 1.402 (5) | C11A—C16A | 1.399 (5) |
C12—C13 | 1.391 (5) | C12A—C13A | 1.398 (5) |
C13—C14 | 1.377 (5) | C13A—C14A | 1.375 (5) |
C13—H13 | 0.9500 | C13A—H13A | 0.9500 |
C14—O17 | 1.351 (4) | C14A—O17A | 1.353 (4) |
C14—C15 | 1.424 (5) | C14A—C15A | 1.417 (4) |
C15—O18 | 1.347 (4) | C15A—O18A | 1.343 (4) |
C15—C16 | 1.381 (5) | C15A—C16A | 1.385 (5) |
C16—H16 | 0.9500 | C16A—H16A | 0.9500 |
O17—C17 | 1.432 (4) | O17A—C17A | 1.434 (4) |
C17—H17A | 0.9800 | C17A—H17D | 0.9800 |
C17—H17B | 0.9800 | C17A—H17E | 0.9800 |
C17—H17C | 0.9800 | C17A—H17F | 0.9800 |
O18—C18 | 1.436 (4) | O18A—C18A | 1.431 (4) |
C18—H18A | 0.9800 | C18A—H18D | 0.9800 |
C18—H18B | 0.9800 | C18A—H18E | 0.9800 |
C18—H18C | 0.9800 | C18A—H18F | 0.9800 |
C21—C26 | 1.393 (5) | C21A—C26A | 1.393 (5) |
C21—C22 | 1.400 (5) | C21A—C22A | 1.399 (5) |
C22—C23 | 1.379 (5) | C22A—C23A | 1.381 (5) |
C23—C24 | 1.384 (5) | C23A—C24A | 1.387 (5) |
C23—H23 | 0.9500 | C23A—H23A | 0.9500 |
C24—C25 | 1.379 (5) | C24A—C25A | 1.383 (5) |
C25—C26 | 1.388 (5) | C25A—C26A | 1.383 (5) |
C25—H25 | 0.9500 | C25A—H25A | 0.9500 |
C26—H26 | 0.9500 | C26A—H26A | 0.9500 |
O2—N1—O1 | 123.1 (3) | O1A—N1A—O2A | 122.9 (4) |
O2—N1—C12 | 118.1 (3) | O1A—N1A—C12A | 118.5 (4) |
O1—N1—C12 | 118.8 (3) | O2A—N1A—C12A | 118.5 (3) |
C11—C1—C2 | 116.2 (3) | C2A—C1A—C11A | 115.4 (3) |
C11—C1—Br1 | 109.2 (2) | C2A—C1A—Br1A | 103.3 (2) |
C2—C1—Br1 | 104.8 (2) | C11A—C1A—Br1A | 110.6 (2) |
C11—C1—H1 | 108.8 | C2A—C1A—H1A | 109.1 |
C2—C1—H1 | 108.8 | C11A—C1A—H1A | 109.1 |
Br1—C1—H1 | 108.8 | Br1A—C1A—H1A | 109.1 |
C1—C2—C3 | 112.0 (3) | C1A—C2A—C3A | 112.9 (3) |
C1—C2—Br2 | 108.9 (2) | C1A—C2A—Br2A | 109.6 (2) |
C3—C2—Br2 | 102.8 (2) | C3A—C2A—Br2A | 101.7 (2) |
C1—C2—H2 | 111.0 | C1A—C2A—H2A | 110.8 |
C3—C2—H2 | 111.0 | C3A—C2A—H2A | 110.8 |
Br2—C2—H2 | 111.0 | Br2A—C2A—H2A | 110.8 |
O3—C3—C21 | 121.7 (3) | O3A—C3A—C21A | 123.1 (3) |
O3—C3—C2 | 119.7 (3) | O3A—C3A—C2A | 120.8 (3) |
C21—C3—C2 | 118.5 (3) | C21A—C3A—C2A | 115.9 (3) |
C12—C11—C16 | 116.3 (3) | C12A—C11A—C16A | 116.4 (3) |
C12—C11—C1 | 124.2 (3) | C12A—C11A—C1A | 124.0 (3) |
C16—C11—C1 | 119.5 (3) | C16A—C11A—C1A | 119.6 (3) |
C11—C12—C13 | 123.1 (3) | C11A—C12A—C13A | 122.8 (3) |
C11—C12—N1 | 121.5 (3) | C11A—C12A—N1A | 121.8 (3) |
C13—C12—N1 | 115.4 (3) | C13A—C12A—N1A | 115.4 (3) |
C14—C13—C12 | 119.9 (3) | C14A—C13A—C12A | 119.8 (3) |
C14—C13—H13 | 120.1 | C14A—C13A—H13A | 120.1 |
C12—C13—H13 | 120.1 | C12A—C13A—H13A | 120.1 |
O17—C14—C13 | 125.2 (3) | O17A—C14A—C13A | 125.9 (3) |
O17—C14—C15 | 116.0 (3) | O17A—C14A—C15A | 115.3 (3) |
C13—C14—C15 | 118.8 (3) | C13A—C14A—C15A | 118.8 (3) |
O18—C15—C16 | 125.5 (3) | O18A—C15A—C16A | 125.2 (3) |
O18—C15—C14 | 115.0 (3) | O18A—C15A—C14A | 114.6 (3) |
C16—C15—C14 | 119.5 (3) | C16A—C15A—C14A | 120.2 (3) |
C15—C16—C11 | 122.4 (3) | C15A—C16A—C11A | 121.9 (3) |
C15—C16—H16 | 118.8 | C15A—C16A—H16A | 119.0 |
C11—C16—H16 | 118.8 | C11A—C16A—H16A | 119.0 |
C14—O17—C17 | 117.0 (3) | C14A—O17A—C17A | 117.2 (3) |
O17—C17—H17A | 109.5 | O17A—C17A—H17D | 109.5 |
O17—C17—H17B | 109.5 | O17A—C17A—H17E | 109.5 |
H17A—C17—H17B | 109.5 | H17D—C17A—H17E | 109.5 |
O17—C17—H17C | 109.5 | O17A—C17A—H17F | 109.5 |
H17A—C17—H17C | 109.5 | H17D—C17A—H17F | 109.5 |
H17B—C17—H17C | 109.5 | H17E—C17A—H17F | 109.5 |
C15—O18—C18 | 117.4 (3) | C15A—O18A—C18A | 118.4 (3) |
O18—C18—H18A | 109.5 | O18A—C18A—H18D | 109.5 |
O18—C18—H18B | 109.5 | O18A—C18A—H18E | 109.5 |
H18A—C18—H18B | 109.5 | H18D—C18A—H18E | 109.5 |
O18—C18—H18C | 109.5 | O18A—C18A—H18F | 109.5 |
H18A—C18—H18C | 109.5 | H18D—C18A—H18F | 109.5 |
H18B—C18—H18C | 109.5 | H18E—C18A—H18F | 109.5 |
C26—C21—C22 | 118.5 (3) | C26A—C21A—C22A | 117.5 (3) |
C26—C21—C3 | 119.7 (3) | C26A—C21A—C3A | 119.8 (3) |
C22—C21—C3 | 121.7 (3) | C22A—C21A—C3A | 122.7 (3) |
C23—C22—C21 | 121.1 (3) | C23A—C22A—C21A | 121.8 (3) |
C23—C22—Cl1 | 117.3 (3) | C23A—C22A—Cl1A | 117.1 (3) |
C21—C22—Cl1 | 121.5 (3) | C21A—C22A—Cl1A | 121.0 (3) |
C22—C23—C24 | 119.0 (3) | C22A—C23A—C24A | 118.4 (3) |
C22—C23—H23 | 120.5 | C22A—C23A—H23A | 120.8 |
C24—C23—H23 | 120.5 | C24A—C23A—H23A | 120.8 |
C25—C24—C23 | 121.6 (3) | C25A—C24A—C23A | 121.9 (3) |
C25—C24—Cl2 | 120.2 (3) | C25A—C24A—Cl2A | 119.9 (3) |
C23—C24—Cl2 | 118.2 (3) | C23A—C24A—Cl2A | 118.3 (3) |
C24—C25—C26 | 119.0 (3) | C26A—C25A—C24A | 118.3 (3) |
C24—C25—H25 | 120.5 | C26A—C25A—H25A | 120.8 |
C26—C25—H25 | 120.5 | C24A—C25A—H25A | 120.8 |
C25—C26—C21 | 121.0 (3) | C25A—C26A—C21A | 122.0 (3) |
C25—C26—H26 | 119.5 | C25A—C26A—H26A | 119.0 |
C21—C26—H26 | 119.5 | C21A—C26A—H26A | 119.0 |
C11—C1—C2—C3 | 171.7 (3) | C11A—C1A—C2A—C3A | 168.1 (3) |
Br1—C1—C2—C3 | −67.7 (3) | Br1A—C1A—C2A—C3A | −71.1 (3) |
C11—C1—C2—Br2 | 58.7 (3) | C11A—C1A—C2A—Br2A | 55.6 (4) |
Br1—C1—C2—Br2 | 179.31 (15) | Br1A—C1A—C2A—Br2A | 176.42 (15) |
C1—C2—C3—O3 | −19.6 (5) | C1A—C2A—C3A—O3A | −23.2 (5) |
Br2—C2—C3—O3 | 97.1 (3) | Br2A—C2A—C3A—O3A | 94.1 (3) |
C1—C2—C3—C21 | 162.6 (3) | C1A—C2A—C3A—C21A | 162.0 (3) |
Br2—C2—C3—C21 | −80.7 (3) | Br2A—C2A—C3A—C21A | −80.7 (3) |
C2—C1—C11—C12 | −131.5 (4) | C2A—C1A—C11A—C12A | −137.7 (4) |
Br1—C1—C11—C12 | 110.4 (3) | Br1A—C1A—C11A—C12A | 105.6 (4) |
C2—C1—C11—C16 | 47.9 (5) | C2A—C1A—C11A—C16A | 38.8 (5) |
Br1—C1—C11—C16 | −70.3 (4) | Br1A—C1A—C11A—C16A | −78.0 (4) |
C16—C11—C12—C13 | −1.6 (5) | C16A—C11A—C12A—C13A | −3.7 (6) |
C1—C11—C12—C13 | 177.7 (3) | C1A—C11A—C12A—C13A | 172.9 (4) |
C16—C11—C12—N1 | 179.1 (3) | C16A—C11A—C12A—N1A | 173.5 (4) |
C1—C11—C12—N1 | −1.6 (5) | C1A—C11A—C12A—N1A | −9.9 (6) |
O2—N1—C12—C11 | 141.6 (4) | O1A—N1A—C12A—C11A | 156.9 (4) |
O1—N1—C12—C11 | −40.5 (5) | O2A—N1A—C12A—C11A | −27.1 (6) |
O2—N1—C12—C13 | −37.8 (5) | O1A—N1A—C12A—C13A | −25.8 (6) |
O1—N1—C12—C13 | 140.2 (3) | O2A—N1A—C12A—C13A | 150.3 (4) |
C11—C12—C13—C14 | 3.2 (5) | C11A—C12A—C13A—C14A | 2.6 (6) |
N1—C12—C13—C14 | −177.5 (3) | N1A—C12A—C13A—C14A | −174.8 (3) |
C12—C13—C14—O17 | 177.4 (3) | C12A—C13A—C14A—O17A | 179.8 (3) |
C12—C13—C14—C15 | −2.8 (5) | C12A—C13A—C14A—C15A | 1.0 (5) |
O17—C14—C15—O18 | 0.7 (4) | O17A—C14A—C15A—O18A | −0.9 (4) |
C13—C14—C15—O18 | −179.2 (3) | C13A—C14A—C15A—O18A | 178.0 (3) |
O17—C14—C15—C16 | −179.2 (3) | O17A—C14A—C15A—C16A | 177.8 (3) |
C13—C14—C15—C16 | 1.0 (5) | C13A—C14A—C15A—C16A | −3.2 (5) |
O18—C15—C16—C11 | −179.3 (3) | O18A—C15A—C16A—C11A | −179.3 (3) |
C14—C15—C16—C11 | 0.6 (5) | C14A—C15A—C16A—C11A | 2.1 (5) |
C12—C11—C16—C15 | −0.3 (5) | C12A—C11A—C16A—C15A | 1.3 (5) |
C1—C11—C16—C15 | −179.6 (3) | C1A—C11A—C16A—C15A | −175.4 (3) |
C13—C14—O17—C17 | 22.1 (5) | C13A—C14A—O17A—C17A | 16.5 (5) |
C15—C14—O17—C17 | −157.8 (3) | C15A—C14A—O17A—C17A | −164.7 (3) |
C16—C15—O18—C18 | −5.7 (5) | C16A—C15A—O18A—C18A | 5.1 (5) |
C14—C15—O18—C18 | 174.5 (3) | C14A—C15A—O18A—C18A | −176.3 (3) |
O3—C3—C21—C26 | 137.2 (4) | O3A—C3A—C21A—C26A | 130.9 (4) |
C2—C3—C21—C26 | −45.0 (5) | C2A—C3A—C21A—C26A | −54.5 (4) |
O3—C3—C21—C22 | −38.0 (5) | O3A—C3A—C21A—C22A | −47.9 (5) |
C2—C3—C21—C22 | 139.8 (3) | C2A—C3A—C21A—C22A | 126.7 (3) |
C26—C21—C22—C23 | −1.4 (5) | C26A—C21A—C22A—C23A | 2.3 (5) |
C3—C21—C22—C23 | 173.9 (3) | C3A—C21A—C22A—C23A | −178.8 (3) |
C26—C21—C22—Cl1 | 176.0 (3) | C26A—C21A—C22A—Cl1A | 179.7 (3) |
C3—C21—C22—Cl1 | −8.8 (5) | C3A—C21A—C22A—Cl1A | −1.5 (5) |
C21—C22—C23—C24 | 0.3 (5) | C21A—C22A—C23A—C24A | −1.6 (5) |
Cl1—C22—C23—C24 | −177.1 (3) | Cl1A—C22A—C23A—C24A | −179.1 (3) |
C22—C23—C24—C25 | 0.5 (5) | C22A—C23A—C24A—C25A | −0.6 (5) |
C22—C23—C24—Cl2 | −178.9 (3) | C22A—C23A—C24A—Cl2A | 178.9 (3) |
C23—C24—C25—C26 | −0.1 (6) | C23A—C24A—C25A—C26A | 2.0 (5) |
Cl2—C24—C25—C26 | 179.2 (3) | Cl2A—C24A—C25A—C26A | −177.5 (3) |
C24—C25—C26—C21 | −1.0 (6) | C24A—C25A—C26A—C21A | −1.2 (5) |
C22—C21—C26—C25 | 1.7 (5) | C22A—C21A—C26A—C25A | −0.9 (5) |
C3—C21—C26—C25 | −173.7 (3) | C3A—C21A—C26A—C25A | −179.7 (3) |