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The crystal structure of the title compound, C19H13BrN2O2S, contains two mol­ecules (A and B) in the asymmetric unit. The planar coumarin systems make dihedral angles of 5.47 (1) and 6.42 (1)° with the thia­zole rings in the two unique mol­ecules. The structure is stabilized by inter­molecular N—H...N, N—H...O, C—H...O and C—H...π hydrogen bonds and aromatic stacking inter­actions; intra­molecular C—H...O hydrogen bonds also influence the mol­ecular conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019994/sj2082sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019994/sj2082Isup2.hkl
Contains datablock I

CCDC reference: 613819

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.091
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.58 Ratio PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

3-(2-Anilino-1,3-thiazol-4-yl)-2H-chromen-2-one top
Crystal data top
C19H13BrN2O2SZ = 4
Mr = 413.28F(000) = 832
Triclinic, P1Dx = 1.598 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.940 (7) ÅCell parameters from 625 reflections
b = 12.172 (8) Åθ = 1.4–25.6°
c = 15.039 (10) ŵ = 2.53 mm1
α = 93.025 (10)°T = 290 K
β = 108.484 (10)°Needle, yellow
γ = 112.653 (9)°0.36 × 0.06 × 0.05 mm
V = 1717 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
6816 independent reflections
Radiation source: fine-focus sealed tube5066 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.463, Tmax = 0.884k = 1515
17861 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0469P)2 + 0.3557P]
where P = (Fo2 + 2Fc2)/3
6816 reflections(Δ/σ)max = 0.018
461 parametersΔρmax = 0.72 e Å3
0 restraintsΔρmin = 0.53 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.52445 (4)0.32661 (3)0.02141 (2)0.05893 (11)
Br20.42374 (4)0.69624 (3)0.62613 (2)0.06852 (13)
S10.08557 (8)0.26173 (6)0.12186 (5)0.04264 (17)
S20.26814 (8)0.18085 (6)0.43050 (5)0.04228 (17)
O10.1056 (2)0.08726 (19)0.13853 (13)0.0542 (5)
O20.2154 (2)0.02802 (17)0.14249 (12)0.0459 (5)
O30.5239 (2)0.26594 (15)0.74310 (12)0.0430 (4)
O40.4957 (2)0.07761 (17)0.71794 (13)0.0578 (6)
N10.1682 (2)0.1955 (2)0.29409 (15)0.0417 (5)
N20.2038 (2)0.11413 (18)0.16415 (14)0.0352 (5)
N30.2655 (2)0.02860 (18)0.41519 (14)0.0361 (5)
N40.1428 (2)0.11534 (19)0.27029 (15)0.0453 (6)
C10.3851 (3)0.2304 (3)0.1248 (2)0.0474 (7)
C20.4256 (3)0.2311 (2)0.02716 (19)0.0407 (6)
C30.3979 (3)0.1634 (2)0.03383 (18)0.0384 (6)
C40.3257 (3)0.0932 (2)0.00347 (17)0.0339 (5)
C50.2854 (3)0.0950 (2)0.10167 (17)0.0391 (6)
C60.3149 (3)0.1623 (3)0.16217 (19)0.0518 (7)
C70.2908 (3)0.0191 (2)0.05274 (17)0.0342 (6)
C80.2175 (3)0.0441 (2)0.01221 (17)0.0342 (6)
C90.1743 (3)0.0392 (2)0.09180 (18)0.0396 (6)
C100.1773 (3)0.1190 (2)0.06709 (17)0.0341 (6)
C110.1160 (3)0.1928 (2)0.03334 (19)0.0421 (6)
C120.1608 (3)0.1847 (2)0.20114 (17)0.0340 (5)
C130.1181 (3)0.2702 (2)0.33351 (18)0.0408 (6)
C140.1663 (3)0.3917 (3)0.3262 (2)0.0537 (8)
C150.1132 (5)0.4645 (3)0.3584 (2)0.0748 (11)
C160.0170 (5)0.4186 (4)0.4004 (3)0.0873 (13)
C170.0250 (4)0.3008 (4)0.4132 (2)0.0749 (11)
C180.0227 (3)0.2223 (3)0.37921 (19)0.0493 (7)
C190.0287 (4)0.0926 (3)0.3903 (2)0.0676 (9)
C200.4549 (3)0.5596 (2)0.66092 (19)0.0423 (6)
C210.5305 (3)0.5656 (2)0.75656 (19)0.0421 (6)
C220.5536 (3)0.4662 (2)0.78315 (18)0.0407 (6)
C230.5015 (3)0.3638 (2)0.71389 (17)0.0353 (6)
C240.4271 (3)0.3571 (2)0.61766 (17)0.0348 (6)
C250.4042 (3)0.4580 (2)0.59162 (19)0.0451 (7)
C260.3777 (3)0.2468 (2)0.55138 (18)0.0388 (6)
C270.3962 (3)0.1486 (2)0.57929 (17)0.0331 (5)
C280.4717 (3)0.1561 (2)0.68148 (18)0.0397 (6)
C290.3415 (3)0.0347 (2)0.51136 (17)0.0324 (5)
C300.3532 (3)0.0680 (2)0.53197 (18)0.0404 (6)
C310.2201 (3)0.0796 (2)0.36530 (17)0.0348 (6)
C320.1237 (4)0.2718 (4)0.2884 (3)0.0756 (10)
C330.0565 (3)0.3164 (3)0.2304 (2)0.0517 (7)
C340.0710 (3)0.2411 (2)0.22322 (17)0.0396 (6)
C350.1310 (3)0.2841 (3)0.1703 (2)0.0509 (7)
C360.0639 (4)0.4041 (3)0.1225 (2)0.0715 (10)
C370.0624 (4)0.4793 (3)0.1283 (3)0.0786 (11)
C380.1208 (4)0.4354 (3)0.1807 (3)0.0731 (10)
H10.40600.27620.16430.057*
H30.42680.16450.09890.046*
H60.28730.16110.22720.062*
H70.31940.01460.11850.041*
H110.09310.20490.02930.051*
H140.23510.42400.29940.064*
H150.14320.54500.35110.090*
H160.02060.46730.42090.105*
H170.08740.27230.44540.090*
H19A0.05850.04070.33000.101*
H19B0.10760.07240.41130.101*
H19C0.04690.08140.43680.101*
H210.56490.63570.80200.051*
H220.60340.46830.84660.049*
H250.35540.45660.52810.054*
H260.33120.24240.48680.047*
H300.40070.07680.59260.048*
H32A0.06590.25380.35510.113*
H32B0.21690.33350.27740.113*
H32C0.13100.19960.26980.113*
H350.21690.23230.16650.061*
H360.10450.43330.08670.086*
H370.10820.56020.09670.094*
H380.20750.48740.18320.088*
H1000.200 (3)0.148 (3)0.330 (2)0.051 (8)*
H1010.131 (3)0.067 (3)0.237 (2)0.063 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0751 (2)0.0597 (2)0.0688 (2)0.04466 (18)0.03829 (18)0.02517 (16)
Br20.1042 (3)0.0483 (2)0.0624 (2)0.0499 (2)0.02014 (19)0.01299 (15)
S10.0504 (4)0.0428 (4)0.0415 (4)0.0285 (3)0.0143 (3)0.0090 (3)
S20.0558 (4)0.0301 (3)0.0373 (4)0.0217 (3)0.0081 (3)0.0071 (3)
O10.0662 (13)0.0663 (14)0.0364 (10)0.0434 (12)0.0079 (10)0.0098 (10)
O20.0578 (12)0.0606 (12)0.0270 (9)0.0353 (10)0.0126 (9)0.0079 (8)
O30.0603 (12)0.0354 (10)0.0290 (9)0.0233 (9)0.0073 (8)0.0056 (8)
O40.0901 (16)0.0431 (11)0.0367 (11)0.0364 (11)0.0080 (10)0.0121 (9)
N10.0591 (15)0.0433 (13)0.0384 (12)0.0319 (12)0.0241 (11)0.0135 (10)
N20.0407 (12)0.0358 (12)0.0322 (11)0.0187 (10)0.0143 (10)0.0063 (9)
N30.0464 (13)0.0323 (11)0.0310 (11)0.0217 (10)0.0098 (10)0.0058 (9)
N40.0613 (15)0.0345 (12)0.0332 (12)0.0244 (11)0.0037 (11)0.0047 (10)
C10.0552 (18)0.0493 (17)0.0439 (16)0.0270 (15)0.0211 (14)0.0021 (13)
C20.0415 (15)0.0353 (14)0.0483 (16)0.0165 (12)0.0200 (13)0.0097 (12)
C30.0406 (15)0.0418 (15)0.0347 (14)0.0172 (13)0.0162 (12)0.0103 (11)
C40.0328 (14)0.0330 (13)0.0309 (13)0.0094 (11)0.0116 (11)0.0036 (10)
C50.0410 (15)0.0428 (15)0.0328 (14)0.0196 (13)0.0107 (12)0.0058 (11)
C60.0615 (19)0.067 (2)0.0301 (14)0.0315 (17)0.0158 (14)0.0047 (13)
C70.0370 (14)0.0356 (14)0.0271 (12)0.0130 (12)0.0115 (11)0.0051 (10)
C80.0348 (14)0.0337 (13)0.0318 (13)0.0127 (12)0.0116 (11)0.0060 (10)
C90.0401 (15)0.0436 (15)0.0322 (14)0.0180 (13)0.0098 (12)0.0040 (12)
C100.0340 (14)0.0329 (14)0.0323 (13)0.0128 (11)0.0100 (11)0.0055 (11)
C110.0502 (17)0.0438 (16)0.0339 (14)0.0240 (14)0.0125 (12)0.0064 (12)
C120.0339 (14)0.0310 (13)0.0379 (14)0.0135 (11)0.0144 (11)0.0079 (11)
C130.0503 (17)0.0467 (16)0.0310 (13)0.0289 (14)0.0121 (12)0.0052 (12)
C140.071 (2)0.0465 (18)0.0470 (17)0.0304 (16)0.0194 (15)0.0047 (14)
C150.122 (3)0.066 (2)0.0505 (19)0.061 (2)0.024 (2)0.0018 (17)
C160.136 (4)0.110 (3)0.059 (2)0.096 (3)0.036 (2)0.009 (2)
C170.087 (3)0.120 (3)0.052 (2)0.068 (3)0.0388 (19)0.020 (2)
C180.0518 (18)0.070 (2)0.0353 (15)0.0341 (16)0.0165 (14)0.0115 (14)
C190.062 (2)0.090 (3)0.066 (2)0.035 (2)0.0353 (18)0.0326 (19)
C200.0535 (17)0.0350 (15)0.0463 (16)0.0245 (13)0.0202 (14)0.0118 (12)
C210.0486 (16)0.0356 (15)0.0417 (15)0.0158 (13)0.0194 (13)0.0024 (12)
C220.0487 (16)0.0399 (15)0.0306 (13)0.0180 (13)0.0120 (12)0.0057 (11)
C230.0394 (15)0.0333 (14)0.0348 (13)0.0156 (12)0.0147 (12)0.0096 (11)
C240.0405 (15)0.0320 (13)0.0337 (13)0.0173 (12)0.0133 (11)0.0072 (10)
C250.0590 (18)0.0431 (16)0.0343 (14)0.0280 (14)0.0104 (13)0.0080 (12)
C260.0467 (16)0.0400 (15)0.0309 (13)0.0232 (13)0.0094 (12)0.0084 (11)
C270.0369 (14)0.0339 (13)0.0300 (13)0.0173 (11)0.0109 (11)0.0083 (10)
C280.0469 (16)0.0363 (15)0.0344 (14)0.0190 (13)0.0110 (12)0.0079 (11)
C290.0343 (14)0.0307 (13)0.0315 (13)0.0141 (11)0.0103 (11)0.0075 (10)
C300.0486 (16)0.0353 (14)0.0329 (13)0.0204 (13)0.0061 (12)0.0072 (11)
C310.0373 (14)0.0334 (13)0.0351 (14)0.0170 (12)0.0123 (11)0.0085 (11)
C320.071 (2)0.088 (3)0.080 (3)0.034 (2)0.042 (2)0.026 (2)
C330.0548 (19)0.0505 (18)0.0463 (17)0.0222 (16)0.0144 (15)0.0103 (14)
C340.0460 (16)0.0344 (14)0.0308 (13)0.0183 (13)0.0035 (12)0.0034 (11)
C350.0528 (18)0.0512 (18)0.0448 (16)0.0215 (15)0.0145 (14)0.0046 (14)
C360.094 (3)0.063 (2)0.060 (2)0.039 (2)0.025 (2)0.0062 (17)
C370.087 (3)0.045 (2)0.070 (2)0.012 (2)0.009 (2)0.0134 (17)
C380.061 (2)0.053 (2)0.075 (2)0.0018 (18)0.0145 (19)0.0074 (18)
Geometric parameters (Å, º) top
Br1—C21.901 (3)C1—C21.394 (4)
Br2—C201.890 (3)C1—H10.9300
S2—C301.725 (3)C26—H260.9300
S2—C311.748 (3)C4—C31.400 (4)
S1—C111.722 (3)C3—C21.378 (4)
S1—C121.752 (3)C3—H30.9300
O2—C51.365 (3)C30—H300.9300
O2—C91.373 (3)C25—C201.375 (4)
O3—C231.373 (3)C25—H250.9300
O3—C281.384 (3)C21—C221.382 (4)
O4—C281.200 (3)C21—C201.395 (4)
O1—C91.204 (3)C21—H210.9300
N4—C311.351 (3)C11—H110.9300
N4—C341.437 (3)C22—H220.9300
N4—H1010.81 (3)C35—C341.375 (4)
N1—C121.370 (3)C35—C361.386 (4)
N1—C131.418 (3)C35—H350.9300
N1—H1000.90 (3)C33—C341.385 (4)
N3—C311.303 (3)C33—C381.385 (4)
N3—C291.403 (3)C33—C321.504 (4)
N2—C121.302 (3)C6—H60.9300
N2—C101.405 (3)C18—C171.396 (4)
C27—C261.353 (3)C18—C191.497 (5)
C27—C291.465 (3)C19—H19A0.9600
C27—C281.474 (4)C19—H19B0.9600
C24—C251.397 (4)C19—H19C0.9600
C24—C231.398 (4)C14—C151.373 (4)
C24—C261.431 (3)C14—H140.9300
C7—C81.350 (3)C32—H32A0.9600
C7—C41.436 (3)C32—H32B0.9600
C7—H70.9300C32—H32C0.9600
C5—C61.383 (4)C17—C161.372 (6)
C5—C41.397 (3)C17—H170.9300
C8—C101.470 (3)C36—C371.366 (5)
C8—C91.474 (3)C36—H360.9300
C29—C301.347 (3)C38—C371.361 (5)
C23—C221.379 (3)C38—H380.9300
C13—C181.389 (4)C15—C161.351 (6)
C13—C141.390 (4)C15—H150.9300
C10—C111.347 (4)C37—H370.9300
C1—C61.364 (4)C16—H160.9300
C30—S2—C3188.87 (13)C22—C21—C20119.3 (2)
C11—S1—C1288.70 (13)C22—C21—H21120.3
C5—O2—C9122.8 (2)C20—C21—H21120.3
C23—O3—C28122.9 (2)C10—C11—S1110.8 (2)
C31—N4—C34122.1 (2)C10—C11—H11124.6
C31—N4—H101122 (2)S1—C11—H11124.6
C34—N4—H101116 (2)O4—C28—O3115.4 (2)
C12—N1—C13123.2 (2)O4—C28—C27127.2 (2)
C12—N1—H100118.0 (18)O3—C28—C27117.4 (2)
C13—N1—H100118.6 (18)C23—C22—C21118.8 (2)
C31—N3—C29110.1 (2)C23—C22—H22120.6
C12—N2—C10109.8 (2)C21—C22—H22120.6
C26—C27—C29122.0 (2)C34—C35—C36120.2 (3)
C26—C27—C28118.8 (2)C34—C35—H35119.9
C29—C27—C28119.2 (2)C36—C35—H35119.9
C25—C24—C23118.2 (2)C34—C33—C38116.9 (3)
C25—C24—C26123.7 (2)C34—C33—C32122.0 (3)
C23—C24—C26118.1 (2)C38—C33—C32121.1 (3)
C8—C7—C4121.5 (2)C35—C34—C33121.1 (3)
C8—C7—H7119.3C35—C34—N4118.5 (3)
C4—C7—H7119.3C33—C34—N4120.5 (3)
O2—C5—C6116.6 (2)C3—C2—C1121.9 (2)
O2—C5—C4120.8 (2)C3—C2—Br1120.1 (2)
C6—C5—C4122.6 (2)C1—C2—Br1118.1 (2)
C7—C8—C10123.1 (2)C1—C6—C5118.8 (3)
C7—C8—C9119.5 (2)C1—C6—H6120.6
C10—C8—C9117.5 (2)C5—C6—H6120.6
C30—C29—N3115.5 (2)C13—C18—C17116.6 (3)
C30—C29—C27126.6 (2)C13—C18—C19122.0 (3)
N3—C29—C27117.9 (2)C17—C18—C19121.3 (3)
O3—C23—C22117.3 (2)C25—C20—C21121.9 (2)
O3—C23—C24120.3 (2)C25—C20—Br2119.4 (2)
C22—C23—C24122.5 (2)C21—C20—Br2118.7 (2)
C18—C13—C14120.6 (3)C18—C19—H19A109.5
C18—C13—N1120.3 (3)C18—C19—H19B109.5
C14—C13—N1119.1 (3)H19A—C19—H19B109.5
C11—C10—N2115.6 (2)C18—C19—H19C109.5
C11—C10—C8126.3 (2)H19A—C19—H19C109.5
N2—C10—C8118.1 (2)H19B—C19—H19C109.5
C6—C1—C2119.7 (2)C15—C14—C13120.5 (3)
C6—C1—H1120.1C15—C14—H14119.7
C2—C1—H1120.1C13—C14—H14119.7
O1—C9—O2115.3 (2)C33—C32—H32A109.5
O1—C9—C8127.3 (2)C33—C32—H32B109.5
O2—C9—C8117.4 (2)H32A—C32—H32B109.5
C27—C26—C24122.4 (2)C33—C32—H32C109.5
C27—C26—H26118.8H32A—C32—H32C109.5
C24—C26—H26118.8H32B—C32—H32C109.5
C5—C4—C3117.9 (2)C16—C17—C18122.0 (3)
C5—C4—C7117.9 (2)C16—C17—H17119.0
C3—C4—C7124.2 (2)C18—C17—H17119.0
N3—C31—N4125.1 (2)C37—C36—C35119.4 (3)
N3—C31—S2114.83 (19)C37—C36—H36120.3
N4—C31—S2120.11 (19)C35—C36—H36120.3
N2—C12—N1123.2 (2)C37—C38—C33122.7 (3)
N2—C12—S1115.06 (19)C37—C38—H38118.6
N1—C12—S1121.66 (19)C33—C38—H38118.6
C2—C3—C4119.1 (2)C16—C15—C14119.7 (4)
C2—C3—H3120.5C16—C15—H15120.2
C4—C3—H3120.5C14—C15—H15120.2
C29—C30—S2110.66 (19)C38—C37—C36119.7 (3)
C29—C30—H30124.7C38—C37—H37120.1
S2—C30—H30124.7C36—C37—H37120.1
C20—C25—C24119.2 (2)C15—C16—C17120.3 (3)
C20—C25—H25120.4C15—C16—H16119.8
C24—C25—H25120.4C17—C16—H16119.8
C9—O2—C5—C6177.4 (2)C7—C4—C3—C2180.0 (2)
C9—O2—C5—C43.4 (4)N3—C29—C30—S20.1 (3)
C4—C7—C8—C10178.7 (2)C27—C29—C30—S2178.1 (2)
C4—C7—C8—C91.1 (4)C31—S2—C30—C290.4 (2)
C31—N3—C29—C300.6 (3)C23—C24—C25—C200.2 (4)
C31—N3—C29—C27177.7 (2)C26—C24—C25—C20179.4 (3)
C26—C27—C29—C30179.4 (3)N2—C10—C11—S10.4 (3)
C28—C27—C29—C300.5 (4)C8—C10—C11—S1179.3 (2)
C26—C27—C29—N31.3 (4)C12—S1—C11—C100.3 (2)
C28—C27—C29—N3177.7 (2)C23—O3—C28—O4177.5 (2)
C28—O3—C23—C22177.1 (2)C23—O3—C28—C273.6 (4)
C28—O3—C23—C242.1 (4)C26—C27—C28—O4179.2 (3)
C25—C24—C23—O3178.7 (2)C29—C27—C28—O40.2 (4)
C26—C24—C23—O31.0 (4)C26—C27—C28—O32.1 (4)
C25—C24—C23—C220.5 (4)C29—C27—C28—O3178.9 (2)
C26—C24—C23—C22179.9 (2)O3—C23—C22—C21178.7 (2)
C12—N1—C13—C18127.0 (3)C24—C23—C22—C210.5 (4)
C12—N1—C13—C1453.2 (4)C20—C21—C22—C230.3 (4)
C12—N2—C10—C110.3 (3)C36—C35—C34—C330.3 (4)
C12—N2—C10—C8179.5 (2)C36—C35—C34—N4179.0 (3)
C7—C8—C10—C11173.6 (3)C38—C33—C34—C351.0 (4)
C9—C8—C10—C116.6 (4)C32—C33—C34—C35179.5 (3)
C7—C8—C10—N26.7 (4)C38—C33—C34—N4178.4 (3)
C9—C8—C10—N2173.1 (2)C32—C33—C34—N41.1 (4)
C5—O2—C9—O1175.5 (2)C31—N4—C34—C35102.6 (3)
C5—O2—C9—C84.2 (4)C31—N4—C34—C3378.0 (4)
C7—C8—C9—O1177.7 (3)C4—C3—C2—C10.7 (4)
C10—C8—C9—O12.1 (4)C4—C3—C2—Br1179.63 (18)
C7—C8—C9—O21.9 (4)C6—C1—C2—C30.6 (4)
C10—C8—C9—O2178.3 (2)C6—C1—C2—Br1179.5 (2)
C29—C27—C26—C24178.1 (2)C2—C1—C6—C50.0 (4)
C28—C27—C26—C240.8 (4)O2—C5—C6—C1179.8 (3)
C25—C24—C26—C27177.2 (3)C4—C5—C6—C10.6 (4)
C23—C24—C26—C272.4 (4)C14—C13—C18—C172.4 (4)
O2—C5—C4—C3179.6 (2)N1—C13—C18—C17177.8 (3)
C6—C5—C4—C30.4 (4)C14—C13—C18—C19178.5 (3)
O2—C5—C4—C70.1 (4)N1—C13—C18—C191.2 (4)
C6—C5—C4—C7179.3 (3)C24—C25—C20—C211.0 (4)
C8—C7—C4—C52.0 (4)C24—C25—C20—Br2179.8 (2)
C8—C7—C4—C3178.2 (2)C22—C21—C20—C251.0 (4)
C29—N3—C31—N4179.7 (2)C22—C21—C20—Br2179.8 (2)
C29—N3—C31—S20.9 (3)C18—C13—C14—C154.4 (4)
C34—N4—C31—N3166.7 (3)N1—C13—C14—C15175.9 (3)
C34—N4—C31—S213.9 (4)C13—C18—C17—C161.5 (5)
C30—S2—C31—N30.7 (2)C19—C18—C17—C16177.5 (3)
C30—S2—C31—N4179.8 (2)C34—C35—C36—C370.1 (5)
C10—N2—C12—N1177.6 (2)C34—C33—C38—C371.3 (5)
C10—N2—C12—S10.0 (3)C32—C33—C38—C37179.2 (3)
C13—N1—C12—N2178.5 (2)C13—C14—C15—C162.4 (5)
C13—N1—C12—S10.9 (4)C33—C38—C37—C360.9 (6)
C11—S1—C12—N20.2 (2)C35—C36—C37—C380.2 (6)
C11—S1—C12—N1177.9 (2)C14—C15—C16—C171.6 (6)
C5—C4—C3—C20.2 (4)C18—C17—C16—C153.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H101···N20.81 (4)2.48 (4)3.245 (4)156 (3)
N1—H100···N30.90 (3)2.17 (3)3.067 (4)177 (3)
C7—H7···N20.932.552.873 (4)101
C26—H26···N30.932.492.841 (4)102
C30—H30···O40.932.252.825 (3)120
C11—H11···O10.932.202.774 (4)120
N4—H101···O1i0.81 (4)2.45 (3)2.970 (4)123 (3)
C32—H32C···O1i0.962.493.262 (5)138
C30—H30···Br2ii0.932.923.504 (3)122
C14—H14···Cg8iii0.932.833.677 (5)152
Symmetry codes: (i) x, y, z; (ii) x, y1, z; (iii) x+1, y+1, z+1.
 

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