Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005490/nc6024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005490/nc6024Isup2.hkl |
CCDC reference: 269824
Key indicators
- Single-crystal X-ray study
- T = 173 K
- R factor = 0.044
- wR factor = 0.102
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); 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 and PLATON (Spek, 2003).
C33H25BrN4 | F(000) = 1144 |
Mr = 557.48 | Dx = 1.376 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 46712 reflections |
a = 10.6150 (6) Å | θ = 3.6–25.6° |
b = 14.9140 (5) Å | µ = 1.56 mm−1 |
c = 17.3961 (9) Å | T = 173 K |
β = 102.263 (4)° | Block, colourless |
V = 2691.2 (2) Å3 | 0.28 × 0.26 × 0.25 mm |
Z = 4 |
Stoe IPDS-II two-circle diffractometer | 4939 independent reflections |
Radiation source: fine-focus sealed tube | 4290 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 25.4°, θmin = 3.6° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −12→12 |
Tmin = 0.670, Tmax = 0.687 | k = −18→17 |
31845 measured reflections | l = −20→20 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.047P)2 + 3.0688P] where P = (Fo2 + 2Fc2)/3 |
4939 reflections | (Δ/σ)max = 0.001 |
343 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.87 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 | ||
N1 | 0.60825 (18) | 0.38667 (14) | 0.73782 (12) | 0.0144 (4) | |
N2 | 0.4869 (2) | 0.41555 (15) | 0.71005 (13) | 0.0200 (5) | |
C3 | 0.4728 (2) | 0.40187 (16) | 0.63327 (14) | 0.0146 (5) | |
N4 | 0.5807 (2) | 0.36741 (17) | 0.61461 (13) | 0.0236 (5) | |
N5 | 0.6660 (2) | 0.35774 (16) | 0.68203 (13) | 0.0210 (5) | |
C1 | 0.6679 (2) | 0.38389 (17) | 0.82493 (14) | 0.0144 (5) | |
C11 | 0.7855 (2) | 0.31968 (16) | 0.83616 (14) | 0.0148 (5) | |
C12 | 0.8971 (2) | 0.34701 (18) | 0.81077 (15) | 0.0188 (5) | |
H12 | 0.8990 | 0.4040 | 0.7866 | 0.023* | |
C13 | 1.0046 (2) | 0.29123 (19) | 0.82080 (17) | 0.0229 (6) | |
H13 | 1.0790 | 0.3100 | 0.8030 | 0.027* | |
C14 | 1.0032 (3) | 0.20779 (19) | 0.85691 (17) | 0.0260 (6) | |
H14 | 1.0765 | 0.1697 | 0.8639 | 0.031* | |
C15 | 0.8939 (3) | 0.1808 (2) | 0.88257 (18) | 0.0290 (7) | |
H15 | 0.8927 | 0.1241 | 0.9073 | 0.035* | |
C16 | 0.7855 (3) | 0.23666 (19) | 0.87217 (16) | 0.0227 (6) | |
H16 | 0.7112 | 0.2175 | 0.8900 | 0.027* | |
C21 | 0.7154 (2) | 0.47861 (17) | 0.85317 (14) | 0.0150 (5) | |
C22 | 0.7998 (2) | 0.48690 (18) | 0.92685 (15) | 0.0199 (5) | |
H22 | 0.8268 | 0.4348 | 0.9574 | 0.024* | |
C23 | 0.8443 (2) | 0.57115 (19) | 0.95558 (16) | 0.0222 (6) | |
H23 | 0.9001 | 0.5761 | 1.0059 | 0.027* | |
C24 | 0.8073 (3) | 0.64799 (19) | 0.91078 (17) | 0.0242 (6) | |
H24 | 0.8381 | 0.7052 | 0.9302 | 0.029* | |
C25 | 0.7250 (3) | 0.64001 (19) | 0.83755 (18) | 0.0265 (6) | |
H25 | 0.6997 | 0.6921 | 0.8067 | 0.032* | |
C26 | 0.6790 (3) | 0.55605 (18) | 0.80889 (16) | 0.0221 (6) | |
H26 | 0.6224 | 0.5516 | 0.7588 | 0.027* | |
C31 | 0.5598 (2) | 0.34901 (17) | 0.86463 (14) | 0.0151 (5) | |
C32 | 0.5364 (2) | 0.38664 (18) | 0.93369 (15) | 0.0186 (5) | |
H32 | 0.5882 | 0.4351 | 0.9578 | 0.022* | |
C33 | 0.4376 (2) | 0.35387 (19) | 0.96782 (16) | 0.0217 (6) | |
H33 | 0.4229 | 0.3800 | 1.0149 | 0.026* | |
C34 | 0.3609 (2) | 0.28314 (19) | 0.93293 (17) | 0.0240 (6) | |
H34 | 0.2932 | 0.2614 | 0.9558 | 0.029* | |
C35 | 0.3836 (3) | 0.24445 (19) | 0.86459 (17) | 0.0245 (6) | |
H35 | 0.3318 | 0.1957 | 0.8410 | 0.029* | |
C36 | 0.4821 (2) | 0.27675 (18) | 0.83041 (15) | 0.0206 (5) | |
H36 | 0.4969 | 0.2498 | 0.7836 | 0.025* | |
C41 | 0.2482 (2) | 0.35903 (17) | 0.56175 (14) | 0.0169 (5) | |
C42 | 0.3512 (2) | 0.42050 (17) | 0.57453 (14) | 0.0155 (5) | |
C43 | 0.3402 (3) | 0.50141 (17) | 0.53305 (16) | 0.0208 (5) | |
H43 | 0.4106 | 0.5421 | 0.5418 | 0.025* | |
C44 | 0.2272 (3) | 0.5233 (2) | 0.47898 (17) | 0.0271 (6) | |
H44 | 0.2204 | 0.5783 | 0.4509 | 0.033* | |
C45 | 0.1250 (3) | 0.4633 (2) | 0.46701 (16) | 0.0285 (6) | |
H45 | 0.0476 | 0.4776 | 0.4305 | 0.034* | |
C46 | 0.1345 (2) | 0.3826 (2) | 0.50772 (16) | 0.0239 (6) | |
H46 | 0.0632 | 0.3427 | 0.4990 | 0.029* | |
C51 | 0.2543 (2) | 0.26879 (17) | 0.59983 (15) | 0.0182 (5) | |
C52 | 0.1558 (2) | 0.23989 (19) | 0.63600 (16) | 0.0229 (6) | |
H52 | 0.0882 | 0.2800 | 0.6406 | 0.028* | |
C53 | 0.1556 (3) | 0.1530 (2) | 0.66529 (16) | 0.0253 (6) | |
H53 | 0.0882 | 0.1348 | 0.6900 | 0.030* | |
C54 | 0.2529 (3) | 0.09229 (18) | 0.65893 (15) | 0.0224 (6) | |
C55 | 0.3529 (3) | 0.12168 (18) | 0.62384 (16) | 0.0234 (6) | |
H55 | 0.4211 | 0.0818 | 0.6201 | 0.028* | |
C56 | 0.3535 (2) | 0.20802 (18) | 0.59453 (16) | 0.0213 (6) | |
H56 | 0.4217 | 0.2264 | 0.5705 | 0.026* | |
C57 | 0.2509 (3) | −0.00222 (19) | 0.68819 (18) | 0.0304 (7) | |
H57A | 0.2758 | −0.0439 | 0.6497 | 0.037* | |
H57B | 0.1627 | −0.0179 | 0.6938 | 0.037* | |
Br1 | 0.37148 (3) | −0.01461 (2) | 0.790376 (18) | 0.03817 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0111 (10) | 0.0200 (10) | 0.0116 (10) | 0.0027 (8) | 0.0018 (8) | −0.0001 (8) |
N2 | 0.0135 (10) | 0.0304 (12) | 0.0151 (11) | 0.0069 (9) | 0.0011 (8) | −0.0013 (9) |
C3 | 0.0154 (12) | 0.0157 (12) | 0.0126 (11) | −0.0014 (9) | 0.0025 (9) | 0.0002 (9) |
N4 | 0.0177 (11) | 0.0395 (14) | 0.0131 (11) | 0.0059 (10) | 0.0021 (9) | −0.0008 (9) |
N5 | 0.0167 (11) | 0.0324 (13) | 0.0146 (11) | 0.0043 (9) | 0.0050 (9) | −0.0015 (9) |
C1 | 0.0117 (11) | 0.0208 (13) | 0.0106 (12) | 0.0018 (10) | 0.0017 (9) | 0.0019 (9) |
C11 | 0.0117 (11) | 0.0196 (12) | 0.0125 (12) | 0.0038 (10) | 0.0008 (9) | −0.0005 (9) |
C12 | 0.0135 (12) | 0.0202 (13) | 0.0222 (13) | −0.0002 (10) | 0.0028 (10) | 0.0021 (10) |
C13 | 0.0120 (12) | 0.0284 (15) | 0.0295 (15) | 0.0001 (10) | 0.0073 (10) | 0.0011 (11) |
C14 | 0.0171 (13) | 0.0315 (15) | 0.0287 (15) | 0.0099 (11) | 0.0036 (11) | 0.0042 (12) |
C15 | 0.0288 (15) | 0.0269 (15) | 0.0334 (16) | 0.0089 (12) | 0.0114 (13) | 0.0150 (12) |
C16 | 0.0182 (13) | 0.0295 (15) | 0.0220 (14) | 0.0048 (11) | 0.0077 (11) | 0.0089 (11) |
C21 | 0.0107 (11) | 0.0202 (12) | 0.0149 (12) | 0.0018 (9) | 0.0046 (9) | 0.0010 (10) |
C22 | 0.0173 (12) | 0.0239 (13) | 0.0181 (12) | 0.0023 (10) | 0.0032 (10) | 0.0017 (10) |
C23 | 0.0147 (12) | 0.0317 (15) | 0.0202 (13) | −0.0035 (11) | 0.0036 (10) | −0.0070 (11) |
C24 | 0.0192 (13) | 0.0235 (14) | 0.0335 (16) | −0.0056 (11) | 0.0139 (12) | −0.0051 (12) |
C25 | 0.0265 (14) | 0.0209 (14) | 0.0328 (16) | −0.0011 (11) | 0.0080 (12) | 0.0062 (12) |
C26 | 0.0204 (13) | 0.0249 (14) | 0.0211 (13) | 0.0028 (11) | 0.0044 (10) | 0.0048 (11) |
C31 | 0.0099 (11) | 0.0206 (12) | 0.0146 (12) | 0.0038 (9) | 0.0022 (9) | 0.0021 (10) |
C32 | 0.0151 (12) | 0.0244 (13) | 0.0165 (13) | 0.0015 (10) | 0.0037 (10) | 0.0006 (10) |
C33 | 0.0196 (13) | 0.0300 (14) | 0.0176 (13) | 0.0051 (11) | 0.0084 (11) | 0.0008 (11) |
C34 | 0.0147 (12) | 0.0304 (15) | 0.0283 (15) | 0.0010 (11) | 0.0075 (11) | 0.0062 (12) |
C35 | 0.0177 (13) | 0.0263 (14) | 0.0286 (15) | −0.0054 (11) | 0.0027 (11) | −0.0011 (12) |
C36 | 0.0177 (13) | 0.0260 (14) | 0.0174 (13) | 0.0003 (11) | 0.0024 (10) | −0.0028 (10) |
C41 | 0.0140 (12) | 0.0231 (13) | 0.0137 (12) | 0.0008 (10) | 0.0036 (9) | −0.0027 (10) |
C42 | 0.0140 (11) | 0.0222 (13) | 0.0096 (11) | 0.0020 (10) | 0.0011 (9) | −0.0021 (9) |
C43 | 0.0217 (13) | 0.0205 (14) | 0.0207 (13) | 0.0016 (10) | 0.0054 (10) | 0.0003 (10) |
C44 | 0.0286 (15) | 0.0272 (15) | 0.0258 (15) | 0.0102 (12) | 0.0066 (12) | 0.0094 (12) |
C45 | 0.0215 (14) | 0.0413 (17) | 0.0201 (14) | 0.0103 (12) | −0.0017 (11) | 0.0042 (12) |
C46 | 0.0140 (12) | 0.0358 (16) | 0.0208 (14) | 0.0012 (11) | 0.0010 (10) | −0.0046 (11) |
C51 | 0.0153 (12) | 0.0225 (13) | 0.0158 (12) | −0.0028 (10) | 0.0014 (10) | −0.0029 (10) |
C52 | 0.0154 (13) | 0.0309 (15) | 0.0235 (14) | −0.0005 (11) | 0.0064 (11) | −0.0021 (11) |
C53 | 0.0193 (13) | 0.0346 (16) | 0.0237 (14) | −0.0093 (12) | 0.0081 (11) | −0.0002 (12) |
C54 | 0.0244 (14) | 0.0242 (14) | 0.0177 (13) | −0.0090 (11) | 0.0025 (11) | 0.0004 (10) |
C55 | 0.0223 (14) | 0.0220 (14) | 0.0264 (15) | 0.0006 (11) | 0.0063 (11) | −0.0001 (11) |
C56 | 0.0180 (13) | 0.0242 (14) | 0.0234 (14) | −0.0028 (10) | 0.0081 (10) | 0.0007 (11) |
C57 | 0.0361 (16) | 0.0272 (16) | 0.0258 (15) | −0.0106 (12) | 0.0018 (12) | 0.0022 (12) |
Br1 | 0.0549 (2) | 0.03184 (17) | 0.02359 (17) | 0.00009 (15) | −0.00102 (13) | 0.00386 (13) |
N1—N5 | 1.325 (3) | C32—C33 | 1.399 (4) |
N1—N2 | 1.347 (3) | C32—H32 | 0.9500 |
N1—C1 | 1.514 (3) | C33—C34 | 1.391 (4) |
N2—C3 | 1.328 (3) | C33—H33 | 0.9500 |
C3—N4 | 1.356 (3) | C34—C35 | 1.388 (4) |
C3—C42 | 1.492 (3) | C34—H34 | 0.9500 |
N4—N5 | 1.328 (3) | C35—C36 | 1.393 (4) |
C1—C21 | 1.545 (3) | C35—H35 | 0.9500 |
C1—C31 | 1.550 (3) | C36—H36 | 0.9500 |
C1—C11 | 1.552 (3) | C41—C46 | 1.408 (4) |
C11—C16 | 1.388 (4) | C41—C42 | 1.408 (3) |
C11—C12 | 1.409 (3) | C41—C51 | 1.495 (4) |
C12—C13 | 1.393 (4) | C42—C43 | 1.398 (4) |
C12—H12 | 0.9500 | C43—C44 | 1.397 (4) |
C13—C14 | 1.396 (4) | C43—H43 | 0.9500 |
C13—H13 | 0.9500 | C44—C45 | 1.387 (4) |
C14—C15 | 1.388 (4) | C44—H44 | 0.9500 |
C14—H14 | 0.9500 | C45—C46 | 1.389 (4) |
C15—C16 | 1.401 (4) | C45—H45 | 0.9500 |
C15—H15 | 0.9500 | C46—H46 | 0.9500 |
C16—H16 | 0.9500 | C51—C52 | 1.399 (4) |
C21—C26 | 1.397 (4) | C51—C56 | 1.407 (4) |
C21—C22 | 1.405 (4) | C52—C53 | 1.392 (4) |
C22—C23 | 1.397 (4) | C52—H52 | 0.9500 |
C22—H22 | 0.9500 | C53—C54 | 1.395 (4) |
C23—C24 | 1.395 (4) | C53—H53 | 0.9500 |
C23—H23 | 0.9500 | C54—C55 | 1.402 (4) |
C24—C25 | 1.388 (4) | C54—C57 | 1.500 (4) |
C24—H24 | 0.9500 | C55—C56 | 1.385 (4) |
C25—C26 | 1.397 (4) | C55—H55 | 0.9500 |
C25—H25 | 0.9500 | C56—H56 | 0.9500 |
C26—H26 | 0.9500 | C57—Br1 | 1.966 (3) |
C31—C32 | 1.395 (3) | C57—H57A | 0.9900 |
C31—C36 | 1.410 (4) | C57—H57B | 0.9900 |
N5—N1—N2 | 113.42 (19) | C33—C32—H32 | 119.6 |
N5—N1—C1 | 124.34 (19) | C34—C33—C32 | 120.1 (2) |
N2—N1—C1 | 122.17 (19) | C34—C33—H33 | 119.9 |
C3—N2—N1 | 101.90 (19) | C32—C33—H33 | 119.9 |
N2—C3—N4 | 112.3 (2) | C35—C34—C33 | 119.8 (2) |
N2—C3—C42 | 123.8 (2) | C35—C34—H34 | 120.1 |
N4—C3—C42 | 123.9 (2) | C33—C34—H34 | 120.1 |
N5—N4—C3 | 106.3 (2) | C34—C35—C36 | 120.3 (3) |
N1—N5—N4 | 106.08 (19) | C34—C35—H35 | 119.9 |
N1—C1—C21 | 109.41 (19) | C36—C35—H35 | 119.9 |
N1—C1—C31 | 105.28 (18) | C35—C36—C31 | 120.6 (2) |
C21—C1—C31 | 112.83 (19) | C35—C36—H36 | 119.7 |
N1—C1—C11 | 107.27 (18) | C31—C36—H36 | 119.7 |
C21—C1—C11 | 108.94 (19) | C46—C41—C42 | 118.0 (2) |
C31—C1—C11 | 112.87 (19) | C46—C41—C51 | 118.1 (2) |
C16—C11—C12 | 118.7 (2) | C42—C41—C51 | 123.8 (2) |
C16—C11—C1 | 122.0 (2) | C43—C42—C41 | 120.2 (2) |
C12—C11—C1 | 119.3 (2) | C43—C42—C3 | 118.7 (2) |
C13—C12—C11 | 120.6 (2) | C41—C42—C3 | 121.1 (2) |
C13—C12—H12 | 119.7 | C44—C43—C42 | 121.0 (2) |
C11—C12—H12 | 119.7 | C44—C43—H43 | 119.5 |
C12—C13—C14 | 120.1 (2) | C42—C43—H43 | 119.5 |
C12—C13—H13 | 119.9 | C45—C44—C43 | 118.9 (3) |
C14—C13—H13 | 119.9 | C45—C44—H44 | 120.6 |
C15—C14—C13 | 119.5 (2) | C43—C44—H44 | 120.6 |
C15—C14—H14 | 120.2 | C44—C45—C46 | 120.8 (2) |
C13—C14—H14 | 120.2 | C44—C45—H45 | 119.6 |
C14—C15—C16 | 120.4 (3) | C46—C45—H45 | 119.6 |
C14—C15—H15 | 119.8 | C45—C46—C41 | 121.1 (3) |
C16—C15—H15 | 119.8 | C45—C46—H46 | 119.5 |
C11—C16—C15 | 120.6 (2) | C41—C46—H46 | 119.5 |
C11—C16—H16 | 119.7 | C52—C51—C56 | 118.2 (2) |
C15—C16—H16 | 119.7 | C52—C51—C41 | 120.7 (2) |
C26—C21—C22 | 118.6 (2) | C56—C51—C41 | 120.9 (2) |
C26—C21—C1 | 123.2 (2) | C53—C52—C51 | 120.7 (2) |
C22—C21—C1 | 118.2 (2) | C53—C52—H52 | 119.6 |
C23—C22—C21 | 120.5 (2) | C51—C52—H52 | 119.6 |
C23—C22—H22 | 119.8 | C52—C53—C54 | 121.1 (2) |
C21—C22—H22 | 119.8 | C52—C53—H53 | 119.4 |
C24—C23—C22 | 120.4 (2) | C54—C53—H53 | 119.4 |
C24—C23—H23 | 119.8 | C53—C54—C55 | 118.2 (2) |
C22—C23—H23 | 119.8 | C53—C54—C57 | 121.3 (3) |
C25—C24—C23 | 119.3 (3) | C55—C54—C57 | 120.5 (3) |
C25—C24—H24 | 120.3 | C56—C55—C54 | 120.9 (3) |
C23—C24—H24 | 120.3 | C56—C55—H55 | 119.5 |
C24—C25—C26 | 120.6 (3) | C54—C55—H55 | 119.5 |
C24—C25—H25 | 119.7 | C55—C56—C51 | 120.8 (2) |
C26—C25—H25 | 119.7 | C55—C56—H56 | 119.6 |
C21—C26—C25 | 120.6 (3) | C51—C56—H56 | 119.6 |
C21—C26—H26 | 119.7 | C54—C57—Br1 | 109.99 (19) |
C25—C26—H26 | 119.7 | C54—C57—H57A | 109.7 |
C32—C31—C36 | 118.4 (2) | Br1—C57—H57A | 109.7 |
C32—C31—C1 | 122.2 (2) | C54—C57—H57B | 109.7 |
C36—C31—C1 | 119.4 (2) | Br1—C57—H57B | 109.7 |
C31—C32—C33 | 120.8 (2) | H57A—C57—H57B | 108.2 |
C31—C32—H32 | 119.6 | ||
N5—N1—N2—C3 | 0.5 (3) | C21—C1—C31—C32 | −17.8 (3) |
C1—N1—N2—C3 | −176.6 (2) | C11—C1—C31—C32 | 106.2 (3) |
N1—N2—C3—N4 | −0.8 (3) | N1—C1—C31—C36 | 43.1 (3) |
N1—N2—C3—C42 | 178.0 (2) | C21—C1—C31—C36 | 162.3 (2) |
N2—C3—N4—N5 | 0.8 (3) | C11—C1—C31—C36 | −73.6 (3) |
C42—C3—N4—N5 | −178.0 (2) | C36—C31—C32—C33 | −0.5 (4) |
N2—N1—N5—N4 | 0.0 (3) | C1—C31—C32—C33 | 179.7 (2) |
C1—N1—N5—N4 | 177.0 (2) | C31—C32—C33—C34 | −0.2 (4) |
C3—N4—N5—N1 | −0.4 (3) | C32—C33—C34—C35 | 0.7 (4) |
N5—N1—C1—C21 | 102.8 (3) | C33—C34—C35—C36 | −0.6 (4) |
N2—N1—C1—C21 | −80.4 (3) | C34—C35—C36—C31 | 0.0 (4) |
N5—N1—C1—C31 | −135.7 (2) | C32—C31—C36—C35 | 0.6 (4) |
N2—N1—C1—C31 | 41.1 (3) | C1—C31—C36—C35 | −179.6 (2) |
N5—N1—C1—C11 | −15.2 (3) | C46—C41—C42—C43 | −1.3 (4) |
N2—N1—C1—C11 | 161.5 (2) | C51—C41—C42—C43 | 176.2 (2) |
N1—C1—C11—C16 | −110.1 (3) | C46—C41—C42—C3 | 177.5 (2) |
C21—C1—C11—C16 | 131.5 (2) | C51—C41—C42—C3 | −5.0 (4) |
C31—C1—C11—C16 | 5.4 (3) | N2—C3—C42—C43 | 97.8 (3) |
N1—C1—C11—C12 | 71.4 (3) | N4—C3—C42—C43 | −83.6 (3) |
C21—C1—C11—C12 | −47.0 (3) | N2—C3—C42—C41 | −81.0 (3) |
C31—C1—C11—C12 | −173.1 (2) | N4—C3—C42—C41 | 97.6 (3) |
C16—C11—C12—C13 | 0.8 (4) | C41—C42—C43—C44 | 0.6 (4) |
C1—C11—C12—C13 | 179.3 (2) | C3—C42—C43—C44 | −178.2 (2) |
C11—C12—C13—C14 | −0.6 (4) | C42—C43—C44—C45 | 0.2 (4) |
C12—C13—C14—C15 | 0.1 (4) | C43—C44—C45—C46 | −0.2 (4) |
C13—C14—C15—C16 | 0.2 (5) | C44—C45—C46—C41 | −0.5 (4) |
C12—C11—C16—C15 | −0.5 (4) | C42—C41—C46—C45 | 1.3 (4) |
C1—C11—C16—C15 | −179.0 (2) | C51—C41—C46—C45 | −176.4 (2) |
C14—C15—C16—C11 | 0.0 (4) | C46—C41—C51—C52 | −50.7 (3) |
N1—C1—C21—C26 | 14.4 (3) | C42—C41—C51—C52 | 131.7 (3) |
C31—C1—C21—C26 | −102.5 (3) | C46—C41—C51—C56 | 123.9 (3) |
C11—C1—C21—C26 | 131.4 (2) | C42—C41—C51—C56 | −53.6 (4) |
N1—C1—C21—C22 | −165.4 (2) | C56—C51—C52—C53 | −0.5 (4) |
C31—C1—C21—C22 | 77.8 (3) | C41—C51—C52—C53 | 174.3 (2) |
C11—C1—C21—C22 | −48.4 (3) | C51—C52—C53—C54 | −0.5 (4) |
C26—C21—C22—C23 | 1.1 (4) | C52—C53—C54—C55 | 1.5 (4) |
C1—C21—C22—C23 | −179.2 (2) | C52—C53—C54—C57 | −178.1 (3) |
C21—C22—C23—C24 | −1.2 (4) | C53—C54—C55—C56 | −1.6 (4) |
C22—C23—C24—C25 | 0.5 (4) | C57—C54—C55—C56 | 178.1 (3) |
C23—C24—C25—C26 | 0.2 (4) | C54—C55—C56—C51 | 0.6 (4) |
C22—C21—C26—C25 | −0.4 (4) | C52—C51—C56—C55 | 0.5 (4) |
C1—C21—C26—C25 | 179.9 (2) | C41—C51—C56—C55 | −174.3 (2) |
C24—C25—C26—C21 | −0.3 (4) | C53—C54—C57—Br1 | −101.6 (3) |
N1—C1—C31—C32 | −137.1 (2) | C55—C54—C57—Br1 | 78.8 (3) |