Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030662/lh2149sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030662/lh2149Isup2.hkl |
CCDC reference: 621406
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.092
- Data-to-parameter ratio = 21.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br1 .. S1 .. 3.20 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.07; Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C24H17N2O2S+·Br−·CH4O | Z = 2 |
Mr = 509.41 | F(000) = 520 |
Triclinic, P1 | Dx = 1.515 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5909 (1) Å | Cell parameters from 37016 reflections |
b = 10.9374 (1) Å | θ = 2.0–30.0° |
c = 11.0418 (2) Å | µ = 1.96 mm−1 |
α = 82.2188 (8)° | T = 160 K |
β = 62.9030 (6)° | Prism, colourless |
γ = 79.2876 (8)° | 0.28 × 0.25 × 0.20 mm |
V = 1116.93 (2) Å3 |
Nonius KappaCCD area-detector diffractometer | 6538 independent reflections |
Radiation source: Nonius FR590 sealed tube generator | 5532 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.057 |
Detector resolution: 10 pixels mm-1 | θmax = 30.0°, θmin = 2.1° |
φ and ω scans with κ offsets | h = −14→14 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −15→15 |
Tmin = 0.565, Tmax = 0.678 | l = −15→15 |
31111 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0463P)2 + 0.3319P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
6538 reflections | Δρmax = 0.56 e Å−3 |
299 parameters | Δρmin = −0.57 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.089 (3) |
Experimental. Solvent used: MeOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.447 (1) Frames collected: 753 Seconds exposure per frame: 10 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 30.0 |
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 | ||
S1 | 0.34396 (4) | 0.45180 (4) | 0.47933 (4) | 0.01926 (10) | |
O41 | 0.42036 (14) | −0.09078 (11) | 0.71941 (14) | 0.0255 (3) | |
O42 | 0.30681 (15) | 0.00728 (13) | 0.60161 (16) | 0.0319 (3) | |
N3 | 0.22315 (14) | 0.31129 (13) | 0.69259 (14) | 0.0176 (3) | |
N21 | 0.07269 (15) | 0.49531 (13) | 0.67969 (15) | 0.0189 (3) | |
H21 | 0.000 (3) | 0.471 (2) | 0.744 (2) | 0.027 (6)* | |
C2 | 0.19820 (17) | 0.42168 (15) | 0.63120 (16) | 0.0179 (3) | |
C4 | 0.36273 (17) | 0.24953 (15) | 0.62103 (17) | 0.0187 (3) | |
C5 | 0.43885 (18) | 0.31166 (16) | 0.50450 (17) | 0.0206 (3) | |
H5 | 0.5343 | 0.2822 | 0.4425 | 0.025* | |
C21 | 0.04956 (18) | 0.61375 (15) | 0.61460 (16) | 0.0185 (3) | |
C22 | 0.14511 (19) | 0.69909 (16) | 0.57640 (19) | 0.0238 (3) | |
H22 | 0.2270 | 0.6796 | 0.5934 | 0.029* | |
C23 | 0.1197 (2) | 0.81339 (17) | 0.5130 (2) | 0.0285 (4) | |
H23 | 0.1854 | 0.8717 | 0.4848 | 0.034* | |
C24 | −0.0017 (2) | 0.84229 (17) | 0.4907 (2) | 0.0298 (4) | |
H24 | −0.0174 | 0.9193 | 0.4449 | 0.036* | |
C25 | −0.0999 (2) | 0.75899 (17) | 0.5352 (2) | 0.0281 (4) | |
H25 | −0.1850 | 0.7807 | 0.5236 | 0.034* | |
C26 | −0.07430 (19) | 0.64388 (17) | 0.59674 (18) | 0.0231 (3) | |
H26 | −0.1410 | 0.5863 | 0.6263 | 0.028* | |
C31 | 0.11776 (17) | 0.26791 (15) | 0.82335 (17) | 0.0183 (3) | |
C32 | 0.0930 (2) | 0.32448 (17) | 0.93871 (18) | 0.0248 (4) | |
H32 | 0.1472 | 0.3872 | 0.9325 | 0.030* | |
C33 | −0.0128 (2) | 0.28755 (19) | 1.06330 (19) | 0.0307 (4) | |
H33 | −0.0316 | 0.3256 | 1.1433 | 0.037* | |
C34 | −0.0909 (2) | 0.19586 (18) | 1.0721 (2) | 0.0302 (4) | |
H34 | −0.1631 | 0.1711 | 1.1579 | 0.036* | |
C35 | −0.0638 (2) | 0.14027 (18) | 0.9559 (2) | 0.0305 (4) | |
H35 | −0.1173 | 0.0769 | 0.9623 | 0.037* | |
C36 | 0.0410 (2) | 0.17621 (17) | 0.82970 (19) | 0.0253 (4) | |
H36 | 0.0593 | 0.1385 | 0.7496 | 0.030* | |
C42 | 0.37537 (19) | 0.01636 (16) | 0.66146 (18) | 0.0233 (3) | |
C43 | 0.41513 (18) | 0.13224 (15) | 0.67738 (17) | 0.0197 (3) | |
C44 | 0.50542 (19) | 0.13010 (16) | 0.73350 (18) | 0.0226 (3) | |
H44 | 0.5332 | 0.2058 | 0.7399 | 0.027* | |
C45 | 0.6552 (2) | 0.00577 (18) | 0.8413 (2) | 0.0320 (4) | |
H45 | 0.6909 | 0.0780 | 0.8449 | 0.038* | |
C46 | 0.6972 (2) | −0.1083 (2) | 0.8930 (2) | 0.0371 (5) | |
H46 | 0.7626 | −0.1144 | 0.9313 | 0.045* | |
C47 | 0.6441 (2) | −0.21433 (19) | 0.8892 (2) | 0.0361 (5) | |
H47 | 0.6721 | −0.2919 | 0.9267 | 0.043* | |
C48 | 0.5510 (2) | −0.20840 (18) | 0.8315 (2) | 0.0318 (4) | |
H48 | 0.5152 | −0.2808 | 0.8284 | 0.038* | |
C49 | 0.51150 (19) | −0.09351 (16) | 0.77837 (19) | 0.0240 (3) | |
C50 | 0.55996 (19) | 0.01471 (16) | 0.78368 (19) | 0.0236 (3) | |
O52 | 0.19235 (14) | 0.55060 (14) | 0.12625 (15) | 0.0303 (3) | |
H52 | 0.222 (3) | 0.539 (3) | 0.047 (3) | 0.043 (7)* | |
C51 | 0.2752 (3) | 0.6140 (2) | 0.1611 (3) | 0.0445 (5) | |
H511 | 0.2949 | 0.6915 | 0.1040 | 0.067* | |
H512 | 0.3658 | 0.5610 | 0.1462 | 0.067* | |
H513 | 0.2222 | 0.6335 | 0.2572 | 0.067* | |
Br1 | 0.624322 (18) | 0.480547 (18) | 0.198808 (18) | 0.02805 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01656 (18) | 0.0218 (2) | 0.01647 (18) | −0.00477 (15) | −0.00482 (15) | 0.00206 (15) |
O41 | 0.0259 (6) | 0.0193 (6) | 0.0321 (7) | −0.0045 (5) | −0.0131 (6) | −0.0008 (5) |
O42 | 0.0331 (7) | 0.0301 (7) | 0.0398 (8) | −0.0052 (6) | −0.0209 (7) | −0.0067 (6) |
N3 | 0.0156 (6) | 0.0191 (6) | 0.0154 (6) | −0.0035 (5) | −0.0049 (5) | 0.0015 (5) |
N21 | 0.0146 (6) | 0.0198 (7) | 0.0184 (7) | −0.0032 (5) | −0.0047 (5) | 0.0026 (5) |
C2 | 0.0175 (7) | 0.0204 (7) | 0.0165 (7) | −0.0056 (6) | −0.0076 (6) | 0.0007 (6) |
C4 | 0.0161 (7) | 0.0201 (8) | 0.0190 (7) | −0.0024 (6) | −0.0068 (6) | −0.0022 (6) |
C5 | 0.0173 (7) | 0.0214 (8) | 0.0202 (8) | −0.0021 (6) | −0.0058 (6) | −0.0019 (6) |
C21 | 0.0196 (7) | 0.0183 (7) | 0.0160 (7) | −0.0012 (6) | −0.0067 (6) | −0.0015 (6) |
C22 | 0.0215 (8) | 0.0233 (8) | 0.0255 (8) | −0.0043 (7) | −0.0091 (7) | −0.0011 (7) |
C23 | 0.0315 (10) | 0.0203 (8) | 0.0304 (10) | −0.0067 (7) | −0.0099 (8) | −0.0008 (7) |
C24 | 0.0449 (11) | 0.0184 (8) | 0.0290 (9) | −0.0014 (8) | −0.0204 (9) | 0.0001 (7) |
C25 | 0.0325 (10) | 0.0248 (9) | 0.0313 (10) | 0.0023 (7) | −0.0192 (8) | −0.0046 (7) |
C26 | 0.0240 (8) | 0.0239 (8) | 0.0243 (8) | −0.0029 (7) | −0.0131 (7) | −0.0018 (7) |
C31 | 0.0152 (7) | 0.0188 (7) | 0.0173 (7) | −0.0025 (6) | −0.0052 (6) | 0.0028 (6) |
C32 | 0.0249 (8) | 0.0293 (9) | 0.0200 (8) | −0.0100 (7) | −0.0082 (7) | 0.0006 (7) |
C33 | 0.0323 (10) | 0.0369 (10) | 0.0186 (8) | −0.0087 (8) | −0.0062 (8) | −0.0010 (7) |
C34 | 0.0240 (9) | 0.0318 (10) | 0.0235 (9) | −0.0067 (7) | −0.0021 (7) | 0.0068 (7) |
C35 | 0.0280 (9) | 0.0268 (9) | 0.0322 (10) | −0.0124 (7) | −0.0081 (8) | 0.0049 (8) |
C36 | 0.0271 (9) | 0.0235 (8) | 0.0248 (9) | −0.0078 (7) | −0.0098 (7) | 0.0001 (7) |
C42 | 0.0205 (8) | 0.0210 (8) | 0.0243 (8) | −0.0020 (6) | −0.0060 (7) | −0.0044 (7) |
C43 | 0.0172 (7) | 0.0180 (7) | 0.0200 (8) | −0.0026 (6) | −0.0048 (6) | −0.0014 (6) |
C44 | 0.0224 (8) | 0.0192 (8) | 0.0240 (8) | −0.0031 (6) | −0.0083 (7) | −0.0014 (6) |
C45 | 0.0341 (10) | 0.0274 (9) | 0.0402 (11) | −0.0028 (8) | −0.0225 (9) | 0.0006 (8) |
C46 | 0.0385 (11) | 0.0375 (11) | 0.0413 (12) | 0.0019 (9) | −0.0257 (10) | −0.0010 (9) |
C47 | 0.0401 (11) | 0.0273 (10) | 0.0365 (11) | 0.0047 (8) | −0.0180 (9) | 0.0026 (8) |
C48 | 0.0338 (10) | 0.0215 (9) | 0.0350 (11) | −0.0021 (8) | −0.0121 (9) | 0.0008 (8) |
C49 | 0.0214 (8) | 0.0222 (8) | 0.0241 (8) | −0.0005 (6) | −0.0072 (7) | −0.0022 (7) |
C50 | 0.0226 (8) | 0.0214 (8) | 0.0252 (8) | −0.0009 (6) | −0.0101 (7) | −0.0010 (7) |
O52 | 0.0220 (6) | 0.0402 (8) | 0.0224 (7) | −0.0081 (6) | −0.0038 (5) | 0.0009 (6) |
C51 | 0.0403 (12) | 0.0597 (15) | 0.0418 (13) | −0.0175 (11) | −0.0240 (11) | 0.0066 (11) |
Br1 | 0.02183 (11) | 0.03659 (13) | 0.02210 (11) | −0.01148 (7) | −0.00354 (7) | −0.00292 (7) |
S1—C2 | 1.7276 (17) | C32—H32 | 0.9500 |
S1—C5 | 1.7329 (17) | C33—C34 | 1.382 (3) |
O41—C42 | 1.370 (2) | C33—H33 | 0.9500 |
O41—C49 | 1.383 (2) | C34—C35 | 1.382 (3) |
O42—C42 | 1.206 (2) | C34—H34 | 0.9500 |
N3—C2 | 1.345 (2) | C35—C36 | 1.391 (3) |
N3—C4 | 1.405 (2) | C35—H35 | 0.9500 |
N3—C31 | 1.449 (2) | C36—H36 | 0.9500 |
N21—C2 | 1.331 (2) | C42—C43 | 1.463 (2) |
N21—C21 | 1.430 (2) | C43—C44 | 1.352 (2) |
N21—H21 | 0.84 (2) | C44—C50 | 1.437 (2) |
C4—C5 | 1.338 (2) | C44—H44 | 0.9500 |
C4—C43 | 1.475 (2) | C45—C46 | 1.383 (3) |
C5—H5 | 0.9500 | C45—C50 | 1.401 (3) |
C21—C26 | 1.388 (2) | C45—H45 | 0.9500 |
C21—C22 | 1.389 (2) | C46—C47 | 1.393 (3) |
C22—C23 | 1.391 (3) | C46—H46 | 0.9500 |
C22—H22 | 0.9500 | C47—C48 | 1.385 (3) |
C23—C24 | 1.388 (3) | C47—H47 | 0.9500 |
C23—H23 | 0.9500 | C48—C49 | 1.388 (3) |
C24—C25 | 1.385 (3) | C48—H48 | 0.9500 |
C24—H24 | 0.9500 | C49—C50 | 1.393 (3) |
C25—C26 | 1.389 (3) | O52—C51 | 1.416 (3) |
C25—H25 | 0.9500 | O52—H52 | 0.80 (3) |
C26—H26 | 0.9500 | C51—H511 | 0.9800 |
C31—C36 | 1.380 (2) | C51—H512 | 0.9800 |
C31—C32 | 1.386 (2) | C51—H513 | 0.9800 |
C32—C33 | 1.387 (3) | ||
C2—S1—C5 | 89.81 (8) | C35—C34—C33 | 119.84 (18) |
C42—O41—C49 | 122.40 (14) | C35—C34—H34 | 120.1 |
C2—N3—C4 | 112.85 (13) | C33—C34—H34 | 120.1 |
C2—N3—C31 | 122.02 (13) | C34—C35—C36 | 120.63 (18) |
C4—N3—C31 | 125.00 (13) | C34—C35—H35 | 119.7 |
C2—N21—C21 | 122.33 (15) | C36—C35—H35 | 119.7 |
C2—N21—H21 | 121.6 (15) | C31—C36—C35 | 118.52 (17) |
C21—N21—H21 | 115.7 (15) | C31—C36—H36 | 120.7 |
N21—C2—N3 | 123.26 (15) | C35—C36—H36 | 120.7 |
N21—C2—S1 | 124.48 (13) | O42—C42—O41 | 117.45 (16) |
N3—C2—S1 | 112.18 (12) | O42—C42—C43 | 125.59 (17) |
C5—C4—N3 | 112.63 (14) | O41—C42—C43 | 116.96 (15) |
C5—C4—C43 | 126.14 (15) | C44—C43—C42 | 120.60 (16) |
N3—C4—C43 | 121.17 (14) | C44—C43—C4 | 121.25 (15) |
C4—C5—S1 | 112.48 (13) | C42—C43—C4 | 117.99 (15) |
C4—C5—H5 | 123.8 | C43—C44—C50 | 120.82 (16) |
S1—C5—H5 | 123.8 | C43—C44—H44 | 119.6 |
C26—C21—C22 | 120.74 (16) | C50—C44—H44 | 119.6 |
C26—C21—N21 | 118.40 (15) | C46—C45—C50 | 119.98 (19) |
C22—C21—N21 | 120.79 (15) | C46—C45—H45 | 120.0 |
C21—C22—C23 | 119.34 (17) | C50—C45—H45 | 120.0 |
C21—C22—H22 | 120.3 | C45—C46—C47 | 120.19 (19) |
C23—C22—H22 | 120.3 | C45—C46—H46 | 119.9 |
C24—C23—C22 | 120.07 (18) | C47—C46—H46 | 119.9 |
C24—C23—H23 | 120.0 | C48—C47—C46 | 121.03 (19) |
C22—C23—H23 | 120.0 | C48—C47—H47 | 119.5 |
C25—C24—C23 | 120.11 (17) | C46—C47—H47 | 119.5 |
C25—C24—H24 | 119.9 | C47—C48—C49 | 118.03 (19) |
C23—C24—H24 | 119.9 | C47—C48—H48 | 121.0 |
C24—C25—C26 | 120.20 (17) | C49—C48—H48 | 121.0 |
C24—C25—H25 | 119.9 | O41—C49—C48 | 116.76 (17) |
C26—C25—H25 | 119.9 | O41—C49—C50 | 120.92 (16) |
C21—C26—C25 | 119.43 (17) | C48—C49—C50 | 122.33 (18) |
C21—C26—H26 | 120.3 | C49—C50—C45 | 118.41 (16) |
C25—C26—H26 | 120.3 | C49—C50—C44 | 117.84 (16) |
C36—C31—C32 | 121.85 (16) | C45—C50—C44 | 123.71 (17) |
C36—C31—N3 | 119.79 (15) | C51—O52—H52 | 116 (2) |
C32—C31—N3 | 118.30 (15) | O52—C51—H511 | 109.5 |
C31—C32—C33 | 118.54 (17) | O52—C51—H512 | 109.5 |
C31—C32—H32 | 120.7 | H511—C51—H512 | 109.5 |
C33—C32—H32 | 120.7 | O52—C51—H513 | 109.5 |
C34—C33—C32 | 120.62 (18) | H511—C51—H513 | 109.5 |
C34—C33—H33 | 119.7 | H512—C51—H513 | 109.5 |
C32—C33—H33 | 119.7 | ||
C21—N21—C2—N3 | 178.40 (15) | C32—C33—C34—C35 | 0.0 (3) |
C21—N21—C2—S1 | −5.1 (2) | C33—C34—C35—C36 | −0.4 (3) |
C4—N3—C2—N21 | 178.93 (15) | C32—C31—C36—C35 | −0.1 (3) |
C31—N3—C2—N21 | −5.0 (2) | N3—C31—C36—C35 | −177.24 (16) |
C4—N3—C2—S1 | 2.07 (17) | C34—C35—C36—C31 | 0.4 (3) |
C31—N3—C2—S1 | 178.11 (12) | C49—O41—C42—O42 | 173.31 (16) |
C5—S1—C2—N21 | −177.74 (15) | C49—O41—C42—C43 | −6.6 (2) |
C5—S1—C2—N3 | −0.94 (13) | O42—C42—C43—C44 | −172.69 (18) |
C2—N3—C4—C5 | −2.5 (2) | O41—C42—C43—C44 | 7.2 (2) |
C31—N3—C4—C5 | −178.36 (15) | O42—C42—C43—C4 | 2.7 (3) |
C2—N3—C4—C43 | 174.76 (15) | O41—C42—C43—C4 | −177.42 (14) |
C31—N3—C4—C43 | −1.1 (2) | C5—C4—C43—C44 | 73.4 (2) |
N3—C4—C5—S1 | 1.72 (19) | N3—C4—C43—C44 | −103.4 (2) |
C43—C4—C5—S1 | −175.34 (13) | C5—C4—C43—C42 | −102.0 (2) |
C2—S1—C5—C4 | −0.48 (14) | N3—C4—C43—C42 | 81.2 (2) |
C2—N21—C21—C26 | 134.22 (17) | C42—C43—C44—C50 | −2.5 (3) |
C2—N21—C21—C22 | −49.0 (2) | C4—C43—C44—C50 | −177.73 (16) |
C26—C21—C22—C23 | −3.4 (3) | C50—C45—C46—C47 | −0.6 (3) |
N21—C21—C22—C23 | 179.84 (16) | C45—C46—C47—C48 | 1.3 (3) |
C21—C22—C23—C24 | 1.2 (3) | C46—C47—C48—C49 | −0.4 (3) |
C22—C23—C24—C25 | 1.9 (3) | C42—O41—C49—C48 | −178.94 (17) |
C23—C24—C25—C26 | −2.9 (3) | C42—O41—C49—C50 | 1.2 (3) |
C22—C21—C26—C25 | 2.4 (3) | C47—C48—C49—O41 | 178.95 (18) |
N21—C21—C26—C25 | 179.25 (16) | C47—C48—C49—C50 | −1.2 (3) |
C24—C25—C26—C21 | 0.7 (3) | O41—C49—C50—C45 | −178.31 (17) |
C2—N3—C31—C36 | 104.48 (19) | C48—C49—C50—C45 | 1.9 (3) |
C4—N3—C31—C36 | −80.0 (2) | O41—C49—C50—C44 | 3.7 (3) |
C2—N3—C31—C32 | −72.8 (2) | C48—C49—C50—C44 | −176.11 (18) |
C4—N3—C31—C32 | 102.75 (19) | C46—C45—C50—C49 | −0.9 (3) |
C36—C31—C32—C33 | −0.3 (3) | C46—C45—C50—C44 | 176.95 (19) |
N3—C31—C32—C33 | 176.88 (16) | C43—C44—C50—C49 | −3.0 (3) |
C31—C32—C33—C34 | 0.4 (3) | C43—C44—C50—C45 | 179.16 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O52i | 0.84 (2) | 1.92 (2) | 2.734 (2) | 165 (2) |
O52—H52···Br1ii | 0.80 (3) | 2.46 (3) | 3.2412 (15) | 164 (3) |
C32—H32···Br1iii | 0.95 | 2.75 | 3.6296 (18) | 153 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+1, −z+1. |