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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o598.
Published online 2009 February 25. doi:  10.1107/S1600536809006151
PMCID: PMC2968632

Benzyl 2-(4-bromo­anilino)-4,4-dimethyl-6-oxo­cyclo­hex-1-enecarbodithio­ate: second triclinic polymorph

Abstract

The title structure, C22H22BrNOS2, is a triclinic modification. Whereas the other reported modification crystallizes with just one mol­ecule in the asymmetric unit, the present modification has Z′ = 2. The six-membered cyclo­hexene ring adopts an envelope conformation, with the C atom bearing the two methyl groups representing the flap. This atom deviates by 0.674 (4) Å from the plane passing through the other five atoms of the ring (r.m.s. deviation = 0.027 Å). For the second independent mol­ecule, the deviation is 0.669 (3) Å and the r.m.s. deviation is 0.010 Å. The mol­ecular conformation of both mol­ecules is stabilized by intra­molecular N—H(...)S hydrogen bonds.

Related literature

For background and the other triclinic modification of C22H22BrNOS2, see: El Ashry et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o598-scheme1.jpg

Experimental

Crystal data

  • C22H22BrNOS2
  • M r = 460.44
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o598-efi1.jpg
  • a = 11.8210 (2) Å
  • b = 12.8904 (2) Å
  • c = 15.8833 (3) Å
  • α = 67.670 (1)°
  • β = 71.434 (1)°
  • γ = 73.283 (1)°
  • V = 2083.56 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.19 mm−1
  • T = 100 K
  • 0.40 × 0.15 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.667, T max = 0.899
  • 19892 measured reflections
  • 9548 independent reflections
  • 7113 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.091
  • S = 1.00
  • 9548 reflections
  • 499 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.80 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006151/bt2877sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006151/bt2877Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

To a solution of 3-(4-bromoanilino)-5,5-dimethyl-cyclohex-2-en-1-one (0.1 mol) in DMSO (20 ml) and sodium hydroxide (0.1 mol) in water (1 ml) was added carbon disulphide (0.3 mol). The mixture was kept at 263 K for 20 min. Benzyl bromide (0.1 mol) was added. The mixture was left for 24 h, after which it was quenched with water (200 ml) and then acidified with 10% hydrochloric acid. The resulting precipitate was collected by filtration, dried and purified on a silica gel column (30% ethyl acetate in hexane) to give orange crystals (40% yield).

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The methyl groups were allowed to rotate but not to tip. The amino H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.88±0.01 Å; their isotropic displacement parameters were freely refined.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) plot of the two indepedent molecules of C22H22BrNOS2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C22H22BrNOS2Z = 4
Mr = 460.44F(000) = 944
Triclinic, P1Dx = 1.468 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.8210 (2) ÅCell parameters from 5387 reflections
b = 12.8904 (2) Åθ = 2.3–28.2°
c = 15.8833 (3) ŵ = 2.19 mm1
α = 67.670 (1)°T = 100 K
β = 71.434 (1)°Prism, orange
γ = 73.283 (1)°0.40 × 0.15 × 0.05 mm
V = 2083.56 (6) Å3

Data collection

Bruker SMART APEX diffractometer9548 independent reflections
Radiation source: fine-focus sealed tube7113 reflections with I > 2σ(I)
graphiteRint = 0.029
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.667, Tmax = 0.899k = −16→16
19892 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0461P)2 + 0.3098P] where P = (Fo2 + 2Fc2)/3
9548 reflections(Δ/σ)max = 0.001
499 parametersΔρmax = 0.64 e Å3
2 restraintsΔρmin = −0.80 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br10.82709 (3)0.56564 (2)0.965667 (18)0.03058 (8)
Br20.99128 (3)0.68807 (2)0.63996 (2)0.03598 (9)
S10.39347 (5)1.31023 (5)0.49538 (4)0.02024 (14)
S20.37604 (6)1.16479 (6)0.69198 (4)0.02758 (16)
S31.27628 (5)−0.14493 (5)1.10260 (4)0.01872 (13)
S41.34366 (5)0.04070 (5)0.92901 (4)0.02128 (14)
O10.53444 (15)1.20078 (15)0.38665 (11)0.0229 (4)
O21.05587 (16)−0.10005 (15)1.18173 (12)0.0284 (4)
N10.57049 (19)0.96785 (18)0.69482 (13)0.0196 (4)
H10.508 (2)1.015 (2)0.7196 (18)0.032 (8)*
N21.12817 (19)0.21396 (17)0.90374 (13)0.0188 (4)
H21.2047 (17)0.180 (2)0.8909 (19)0.030 (8)*
C10.5876 (2)1.1224 (2)0.44225 (16)0.0170 (5)
C20.6995 (2)1.0483 (2)0.40214 (16)0.0194 (5)
H2A0.74411.09710.34320.023*
H2B0.67360.99300.38600.023*
C30.7861 (2)0.9824 (2)0.46599 (16)0.0200 (5)
C40.7094 (2)0.9213 (2)0.56034 (16)0.0203 (5)
H4A0.67850.86270.55230.024*
H4B0.76230.88110.60510.024*
C50.6032 (2)0.9988 (2)0.60205 (16)0.0164 (5)
C60.5432 (2)1.1002 (2)0.54397 (15)0.0154 (5)
C70.8473 (2)1.0645 (3)0.4769 (2)0.0320 (7)
H7A0.78551.12830.49210.048*
H7B0.90561.09390.41820.048*
H7C0.88991.02410.52750.048*
C80.8822 (2)0.8941 (2)0.42616 (18)0.0303 (6)
H8A0.84240.84060.42080.045*
H8B0.93740.85210.46800.045*
H8C0.92840.93290.36410.045*
C90.4444 (2)1.1827 (2)0.57809 (16)0.0180 (5)
C100.2870 (2)1.3944 (2)0.56783 (18)0.0269 (6)
H10A0.21311.36110.60180.032*
H10B0.32491.39710.61410.032*
C110.2561 (2)1.5122 (2)0.50118 (17)0.0232 (5)
C120.1633 (2)1.5403 (2)0.45648 (19)0.0289 (6)
H120.11701.48480.46850.035*
C130.1373 (3)1.6485 (2)0.3944 (2)0.0342 (7)
H130.07201.66740.36530.041*
C140.2052 (3)1.7288 (3)0.3746 (2)0.0353 (7)
H140.18831.80260.33100.042*
C150.2980 (3)1.7010 (2)0.4186 (2)0.0355 (7)
H150.34501.75640.40540.043*
C160.3237 (2)1.5941 (2)0.48143 (19)0.0288 (6)
H160.38791.57640.51140.035*
C170.6270 (2)0.8713 (2)0.75945 (16)0.0187 (5)
C180.6361 (2)0.7603 (2)0.76156 (17)0.0224 (5)
H180.60180.74690.72090.027*
C190.6955 (2)0.6694 (2)0.82331 (17)0.0229 (5)
H190.70490.59360.82350.027*
C200.7409 (2)0.6895 (2)0.88443 (16)0.0204 (5)
C210.7265 (2)0.7985 (2)0.88659 (17)0.0239 (6)
H210.75550.81080.93070.029*
C220.6695 (2)0.8898 (2)0.82369 (17)0.0226 (5)
H220.65940.96530.82450.027*
C231.0611 (2)0.1570 (2)0.98324 (15)0.0166 (5)
C240.9302 (2)0.2136 (2)1.00927 (16)0.0193 (5)
H24A0.88270.19460.97760.023*
H24B0.92520.29740.98460.023*
C250.8708 (2)0.1806 (2)1.11405 (16)0.0194 (5)
C260.8923 (2)0.0509 (2)1.14967 (16)0.0186 (5)
H26A0.86030.02571.21850.022*
H26B0.84540.02511.12210.022*
C271.0235 (2)−0.0064 (2)1.12748 (16)0.0169 (5)
C280.7351 (2)0.2307 (2)1.12632 (18)0.0275 (6)
H28A0.69980.19981.09490.041*
H28B0.72330.31401.09870.041*
H28C0.69520.21041.19320.041*
C290.9267 (2)0.2264 (2)1.16430 (18)0.0265 (6)
H29A1.01280.19071.15890.040*
H29B0.88400.20851.23060.040*
H29C0.91900.30941.13560.040*
C301.1090 (2)0.0481 (2)1.04203 (15)0.0152 (5)
C311.2339 (2)−0.0098 (2)1.02289 (16)0.0166 (5)
C321.4361 (2)−0.1873 (2)1.05017 (17)0.0214 (5)
H32A1.4471−0.18690.98560.026*
H32B1.4845−0.13481.04820.026*
C331.4739 (2)−0.3061 (2)1.11252 (17)0.0207 (5)
C341.4845 (2)−0.4005 (2)1.08631 (19)0.0273 (6)
H341.4704−0.38961.02760.033*
C351.5153 (2)−0.5095 (2)1.1445 (2)0.0336 (7)
H351.5237−0.57311.12510.040*
C361.5339 (2)−0.5270 (2)1.2301 (2)0.0359 (7)
H361.5540−0.60241.27040.043*
C371.5232 (3)−0.4349 (3)1.2572 (2)0.0373 (7)
H371.5354−0.44661.31670.045*
C381.4945 (2)−0.3244 (2)1.19834 (19)0.0286 (6)
H381.4891−0.26111.21720.034*
C391.0933 (2)0.3240 (2)0.84045 (16)0.0189 (5)
C400.9947 (2)0.3501 (2)0.80151 (16)0.0224 (5)
H400.94840.29380.81570.027*
C410.9646 (2)0.4589 (2)0.74193 (17)0.0238 (6)
H410.89610.47870.71620.029*
C421.0350 (2)0.5383 (2)0.72021 (16)0.0238 (6)
C431.1365 (2)0.5124 (2)0.75478 (17)0.0226 (5)
H431.18550.56770.73720.027*
C441.1655 (2)0.4037 (2)0.81590 (16)0.0217 (5)
H441.23470.38380.84090.026*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.03315 (16)0.02846 (16)0.02383 (14)0.00095 (11)−0.01404 (11)−0.00052 (11)
Br20.04175 (18)0.01728 (14)0.02988 (15)0.00188 (12)−0.00511 (12)0.00474 (12)
S10.0217 (3)0.0171 (3)0.0186 (3)0.0022 (2)−0.0048 (2)−0.0066 (3)
S20.0303 (4)0.0259 (4)0.0159 (3)0.0059 (3)−0.0007 (3)−0.0072 (3)
S30.0171 (3)0.0149 (3)0.0184 (3)−0.0002 (2)−0.0038 (2)−0.0014 (2)
S40.0167 (3)0.0201 (3)0.0189 (3)−0.0025 (2)−0.0011 (2)−0.0008 (3)
O10.0242 (9)0.0226 (9)0.0157 (8)0.0037 (7)−0.0061 (7)−0.0043 (7)
O20.0243 (10)0.0178 (9)0.0251 (9)−0.0005 (7)0.0015 (7)0.0040 (8)
N10.0219 (11)0.0185 (11)0.0143 (10)0.0002 (9)−0.0038 (8)−0.0040 (9)
N20.0187 (11)0.0166 (11)0.0156 (10)−0.0005 (8)−0.0034 (8)−0.0018 (8)
C10.0174 (12)0.0163 (12)0.0159 (11)−0.0036 (9)−0.0040 (9)−0.0034 (10)
C20.0171 (12)0.0215 (13)0.0139 (11)−0.0021 (10)−0.0006 (9)−0.0032 (10)
C30.0151 (12)0.0207 (13)0.0162 (11)0.0012 (10)−0.0022 (9)−0.0017 (10)
C40.0186 (12)0.0196 (13)0.0154 (11)0.0007 (10)−0.0019 (9)−0.0026 (10)
C50.0163 (12)0.0170 (12)0.0154 (11)−0.0035 (9)−0.0033 (9)−0.0048 (10)
C60.0132 (11)0.0178 (12)0.0135 (11)−0.0015 (9)−0.0022 (9)−0.0051 (10)
C70.0195 (14)0.0412 (17)0.0360 (16)−0.0087 (12)−0.0041 (12)−0.0127 (14)
C80.0247 (14)0.0311 (15)0.0186 (13)0.0080 (11)−0.0013 (11)−0.0030 (12)
C90.0198 (12)0.0182 (12)0.0155 (11)−0.0019 (9)−0.0056 (9)−0.0050 (10)
C100.0285 (15)0.0233 (14)0.0247 (13)0.0044 (11)−0.0043 (11)−0.0116 (12)
C110.0248 (13)0.0195 (13)0.0228 (13)0.0046 (10)−0.0046 (10)−0.0111 (11)
C120.0299 (15)0.0241 (14)0.0367 (16)0.0000 (11)−0.0115 (12)−0.0146 (13)
C130.0361 (17)0.0325 (16)0.0385 (16)0.0127 (13)−0.0207 (13)−0.0204 (14)
C140.0442 (18)0.0254 (15)0.0269 (15)0.0059 (13)−0.0054 (13)−0.0098 (13)
C150.0333 (16)0.0246 (15)0.0466 (18)−0.0061 (12)0.0009 (14)−0.0172 (14)
C160.0237 (14)0.0288 (15)0.0363 (15)−0.0004 (11)−0.0071 (12)−0.0161 (13)
C170.0155 (12)0.0209 (13)0.0131 (11)−0.0010 (10)−0.0016 (9)−0.0017 (10)
C180.0260 (14)0.0257 (14)0.0173 (12)−0.0080 (11)−0.0071 (10)−0.0047 (11)
C190.0281 (14)0.0187 (13)0.0196 (12)−0.0049 (10)−0.0054 (10)−0.0035 (11)
C200.0170 (12)0.0251 (14)0.0137 (11)−0.0019 (10)−0.0051 (9)−0.0006 (10)
C210.0271 (14)0.0284 (14)0.0185 (12)−0.0035 (11)−0.0086 (10)−0.0086 (11)
C220.0248 (14)0.0215 (13)0.0211 (12)−0.0021 (10)−0.0057 (10)−0.0079 (11)
C230.0192 (12)0.0172 (12)0.0133 (11)−0.0028 (9)−0.0031 (9)−0.0057 (10)
C240.0207 (13)0.0152 (12)0.0166 (12)0.0024 (9)−0.0054 (9)−0.0027 (10)
C250.0204 (12)0.0180 (12)0.0153 (11)0.0002 (10)−0.0016 (9)−0.0051 (10)
C260.0186 (12)0.0206 (13)0.0159 (11)−0.0045 (10)−0.0016 (9)−0.0065 (10)
C270.0187 (12)0.0140 (12)0.0172 (11)−0.0026 (9)−0.0029 (9)−0.0055 (10)
C280.0237 (14)0.0247 (14)0.0233 (13)0.0037 (11)−0.0006 (11)−0.0062 (12)
C290.0298 (15)0.0269 (15)0.0236 (13)−0.0066 (11)0.0001 (11)−0.0130 (12)
C300.0166 (12)0.0157 (12)0.0132 (11)−0.0031 (9)−0.0024 (9)−0.0053 (9)
C310.0202 (12)0.0153 (12)0.0147 (11)−0.0037 (9)−0.0052 (9)−0.0040 (9)
C320.0151 (12)0.0193 (13)0.0224 (12)−0.0010 (10)−0.0021 (10)−0.0023 (11)
C330.0122 (12)0.0204 (13)0.0237 (13)0.0001 (9)−0.0016 (10)−0.0052 (11)
C340.0213 (13)0.0271 (15)0.0301 (14)0.0003 (11)−0.0049 (11)−0.0099 (12)
C350.0258 (15)0.0224 (15)0.0451 (18)−0.0013 (11)−0.0024 (13)−0.0100 (13)
C360.0258 (15)0.0192 (14)0.0414 (17)0.0010 (11)−0.0025 (13)0.0051 (13)
C370.0326 (16)0.0418 (18)0.0252 (14)0.0048 (13)−0.0112 (12)−0.0024 (13)
C380.0272 (15)0.0266 (15)0.0316 (15)0.0006 (11)−0.0116 (12)−0.0092 (12)
C390.0229 (13)0.0159 (12)0.0118 (11)−0.0010 (10)−0.0018 (9)−0.0017 (10)
C400.0298 (14)0.0181 (13)0.0198 (12)−0.0050 (11)−0.0063 (10)−0.0059 (11)
C410.0274 (14)0.0223 (14)0.0177 (12)0.0001 (11)−0.0063 (10)−0.0047 (11)
C420.0320 (15)0.0139 (12)0.0143 (11)0.0017 (10)−0.0019 (10)0.0004 (10)
C430.0274 (14)0.0164 (13)0.0190 (12)−0.0059 (10)0.0000 (10)−0.0032 (10)
C440.0197 (13)0.0229 (13)0.0181 (12)−0.0024 (10)−0.0013 (10)−0.0057 (11)

Geometric parameters (Å, °)

Br1—C201.895 (2)C18—C191.385 (3)
Br2—C421.896 (2)C18—H180.9500
S1—C91.756 (2)C19—C201.378 (3)
S1—C101.824 (2)C19—H190.9500
S2—C91.685 (2)C20—C211.378 (4)
S3—C311.765 (2)C21—C221.385 (3)
S3—C321.820 (2)C21—H210.9500
S4—C311.687 (2)C22—H220.9500
O1—C11.227 (3)C23—C301.431 (3)
O2—C271.225 (3)C23—C241.506 (3)
N1—C51.326 (3)C24—C251.528 (3)
N1—C171.427 (3)C24—H24A0.9900
N1—H10.90 (2)C24—H24B0.9900
N2—C231.325 (3)C25—C261.519 (3)
N2—C391.427 (3)C25—C281.525 (3)
N2—H20.88 (2)C25—C291.530 (3)
C1—C61.471 (3)C26—C271.506 (3)
C1—C21.506 (3)C26—H26A0.9900
C2—C31.518 (3)C26—H26B0.9900
C2—H2A0.9900C27—C301.472 (3)
C2—H2B0.9900C28—H28A0.9800
C3—C81.527 (3)C28—H28B0.9800
C3—C71.528 (4)C28—H28C0.9800
C3—C41.529 (3)C29—H29A0.9800
C4—C51.505 (3)C29—H29B0.9800
C4—H4A0.9900C29—H29C0.9800
C4—H4B0.9900C30—C311.443 (3)
C5—C61.425 (3)C32—C331.504 (3)
C6—C91.452 (3)C32—H32A0.9900
C7—H7A0.9800C32—H32B0.9900
C7—H7B0.9800C33—C381.381 (4)
C7—H7C0.9800C33—C341.390 (4)
C8—H8A0.9800C34—C351.376 (4)
C8—H8B0.9800C34—H340.9500
C8—H8C0.9800C35—C361.370 (4)
C10—C111.505 (3)C35—H350.9500
C10—H10A0.9900C36—C371.371 (4)
C10—H10B0.9900C36—H360.9500
C11—C121.382 (4)C37—C381.389 (4)
C11—C161.389 (4)C37—H370.9500
C12—C131.384 (4)C38—H380.9500
C12—H120.9500C39—C441.387 (3)
C13—C141.372 (4)C39—C401.389 (3)
C13—H130.9500C40—C411.381 (3)
C14—C151.376 (4)C40—H400.9500
C14—H140.9500C41—C421.378 (4)
C15—C161.376 (4)C41—H410.9500
C15—H150.9500C42—C431.380 (4)
C16—H160.9500C43—C441.388 (3)
C17—C221.389 (3)C43—H430.9500
C17—C181.392 (3)C44—H440.9500
C9—S1—C10103.16 (11)C22—C21—H21120.4
C31—S3—C32103.22 (11)C21—C22—C17120.1 (2)
C5—N1—C17127.3 (2)C21—C22—H22119.9
C5—N1—H1116.3 (18)C17—C22—H22119.9
C17—N1—H1116.3 (18)N2—C23—C30122.5 (2)
C23—N2—C39128.3 (2)N2—C23—C24116.2 (2)
C23—N2—H2114.4 (18)C30—C23—C24121.2 (2)
C39—N2—H2117.3 (18)C23—C24—C25115.47 (19)
O1—C1—C6121.6 (2)C23—C24—H24A108.4
O1—C1—C2117.2 (2)C25—C24—H24A108.4
C6—C1—C2121.1 (2)C23—C24—H24B108.4
C1—C2—C3115.15 (19)C25—C24—H24B108.4
C1—C2—H2A108.5H24A—C24—H24B107.5
C3—C2—H2A108.5C26—C25—C28110.6 (2)
C1—C2—H2B108.5C26—C25—C24106.01 (19)
C3—C2—H2B108.5C28—C25—C24108.15 (19)
H2A—C2—H2B107.5C26—C25—C29111.1 (2)
C2—C3—C8110.2 (2)C28—C25—C29110.0 (2)
C2—C3—C7110.0 (2)C24—C25—C29110.8 (2)
C8—C3—C7110.0 (2)C27—C26—C25114.4 (2)
C2—C3—C4106.50 (19)C27—C26—H26A108.6
C8—C3—C4109.4 (2)C25—C26—H26A108.6
C7—C3—C4110.6 (2)C27—C26—H26B108.6
C5—C4—C3114.3 (2)C25—C26—H26B108.6
C5—C4—H4A108.7H26A—C26—H26B107.6
C3—C4—H4A108.7O2—C27—C30121.4 (2)
C5—C4—H4B108.7O2—C27—C26117.9 (2)
C3—C4—H4B108.7C30—C27—C26120.6 (2)
H4A—C4—H4B107.6C25—C28—H28A109.5
N1—C5—C6122.6 (2)C25—C28—H28B109.5
N1—C5—C4116.3 (2)H28A—C28—H28B109.5
C6—C5—C4121.1 (2)C25—C28—H28C109.5
C5—C6—C9124.8 (2)H28A—C28—H28C109.5
C5—C6—C1116.6 (2)H28B—C28—H28C109.5
C9—C6—C1118.6 (2)C25—C29—H29A109.5
C3—C7—H7A109.5C25—C29—H29B109.5
C3—C7—H7B109.5H29A—C29—H29B109.5
H7A—C7—H7B109.5C25—C29—H29C109.5
C3—C7—H7C109.5H29A—C29—H29C109.5
H7A—C7—H7C109.5H29B—C29—H29C109.5
H7B—C7—H7C109.5C23—C30—C31124.3 (2)
C3—C8—H8A109.5C23—C30—C27116.7 (2)
C3—C8—H8B109.5C31—C30—C27119.0 (2)
H8A—C8—H8B109.5C30—C31—S4125.17 (18)
C3—C8—H8C109.5C30—C31—S3118.00 (17)
H8A—C8—H8C109.5S4—C31—S3116.82 (13)
H8B—C8—H8C109.5C33—C32—S3105.03 (16)
C6—C9—S2124.35 (18)C33—C32—H32A110.7
C6—C9—S1117.94 (17)S3—C32—H32A110.7
S2—C9—S1117.71 (14)C33—C32—H32B110.7
C11—C10—S1105.70 (17)S3—C32—H32B110.7
C11—C10—H10A110.6H32A—C32—H32B108.8
S1—C10—H10A110.6C38—C33—C34118.4 (2)
C11—C10—H10B110.6C38—C33—C32121.1 (2)
S1—C10—H10B110.6C34—C33—C32120.5 (2)
H10A—C10—H10B108.7C35—C34—C33120.7 (3)
C12—C11—C16118.7 (2)C35—C34—H34119.7
C12—C11—C10121.4 (3)C33—C34—H34119.7
C16—C11—C10119.9 (2)C36—C35—C34120.6 (3)
C11—C12—C13120.6 (3)C36—C35—H35119.7
C11—C12—H12119.7C34—C35—H35119.7
C13—C12—H12119.7C35—C36—C37119.5 (3)
C14—C13—C12120.4 (3)C35—C36—H36120.3
C14—C13—H13119.8C37—C36—H36120.3
C12—C13—H13119.8C36—C37—C38120.5 (3)
C13—C14—C15119.2 (3)C36—C37—H37119.8
C13—C14—H14120.4C38—C37—H37119.8
C15—C14—H14120.4C33—C38—C37120.4 (3)
C14—C15—C16120.9 (3)C33—C38—H38119.8
C14—C15—H15119.5C37—C38—H38119.8
C16—C15—H15119.5C44—C39—C40120.7 (2)
C15—C16—C11120.2 (3)C44—C39—N2117.0 (2)
C15—C16—H16119.9C40—C39—N2122.2 (2)
C11—C16—H16119.9C41—C40—C39119.3 (2)
C22—C17—C18119.9 (2)C41—C40—H40120.4
C22—C17—N1118.4 (2)C39—C40—H40120.4
C18—C17—N1121.6 (2)C42—C41—C40119.4 (2)
C19—C18—C17119.6 (2)C42—C41—H41120.3
C19—C18—H18120.2C40—C41—H41120.3
C17—C18—H18120.2C41—C42—C43122.2 (2)
C20—C19—C18119.7 (2)C41—C42—Br2119.00 (19)
C20—C19—H19120.1C43—C42—Br2118.8 (2)
C18—C19—H19120.1C42—C43—C44118.4 (2)
C21—C20—C19121.3 (2)C42—C43—H43120.8
C21—C20—Br1119.17 (18)C44—C43—H43120.8
C19—C20—Br1119.56 (19)C39—C44—C43120.0 (2)
C20—C21—C22119.2 (2)C39—C44—H44120.0
C20—C21—H21120.4C43—C44—H44120.0
O1—C1—C2—C3159.1 (2)C39—N2—C23—C30−177.8 (2)
C6—C1—C2—C3−21.9 (3)C39—N2—C23—C241.9 (4)
C1—C2—C3—C8169.2 (2)N2—C23—C24—C25−153.0 (2)
C1—C2—C3—C7−69.3 (3)C30—C23—C24—C2526.7 (3)
C1—C2—C3—C450.6 (3)C23—C24—C25—C26−52.7 (3)
C2—C3—C4—C5−55.0 (3)C23—C24—C25—C28−171.4 (2)
C8—C3—C4—C5−174.1 (2)C23—C24—C25—C2968.0 (3)
C7—C3—C4—C564.6 (3)C28—C25—C26—C27171.30 (19)
C17—N1—C5—C6−177.1 (2)C24—C25—C26—C2754.3 (3)
C17—N1—C5—C42.2 (4)C29—C25—C26—C27−66.1 (3)
C3—C4—C5—N1−148.8 (2)C25—C26—C27—O2150.5 (2)
C3—C4—C5—C630.5 (3)C25—C26—C27—C30−30.8 (3)
N1—C5—C6—C92.6 (4)N2—C23—C30—C311.4 (4)
C4—C5—C6—C9−176.7 (2)C24—C23—C30—C31−178.3 (2)
N1—C5—C6—C1−178.7 (2)N2—C23—C30—C27−178.9 (2)
C4—C5—C6—C12.1 (3)C24—C23—C30—C271.3 (3)
O1—C1—C6—C5172.4 (2)O2—C27—C30—C23179.4 (2)
C2—C1—C6—C5−6.5 (3)C26—C27—C30—C230.7 (3)
O1—C1—C6—C9−8.7 (3)O2—C27—C30—C31−0.9 (3)
C2—C1—C6—C9172.3 (2)C26—C27—C30—C31−179.7 (2)
C5—C6—C9—S2−6.4 (3)C23—C30—C31—S40.1 (3)
C1—C6—C9—S2174.91 (18)C27—C30—C31—S4−179.54 (17)
C5—C6—C9—S1173.03 (18)C23—C30—C31—S3−179.07 (18)
C1—C6—C9—S1−5.7 (3)C27—C30—C31—S31.3 (3)
C10—S1—C9—C6−172.39 (19)C32—S3—C31—C30178.16 (18)
C10—S1—C9—S27.04 (18)C32—S3—C31—S4−1.10 (17)
C9—S1—C10—C11170.72 (18)C31—S3—C32—C33−176.12 (17)
S1—C10—C11—C1286.5 (3)S3—C32—C33—C38−76.0 (3)
S1—C10—C11—C16−91.5 (2)S3—C32—C33—C34101.5 (2)
C16—C11—C12—C13−1.0 (4)C38—C33—C34—C35−0.2 (4)
C10—C11—C12—C13−179.1 (2)C32—C33—C34—C35−177.9 (2)
C11—C12—C13—C141.6 (4)C33—C34—C35—C361.2 (4)
C12—C13—C14—C15−1.2 (4)C34—C35—C36—C37−0.8 (4)
C13—C14—C15—C160.3 (4)C35—C36—C37—C38−0.4 (4)
C14—C15—C16—C110.2 (4)C34—C33—C38—C37−1.0 (4)
C12—C11—C16—C150.1 (4)C32—C33—C38—C37176.6 (2)
C10—C11—C16—C15178.2 (2)C36—C37—C38—C331.4 (4)
C5—N1—C17—C22122.2 (3)C23—N2—C39—C44127.2 (3)
C5—N1—C17—C18−60.3 (3)C23—N2—C39—C40−55.4 (3)
C22—C17—C18—C19−4.7 (4)C44—C39—C40—C41−3.7 (4)
N1—C17—C18—C19177.8 (2)N2—C39—C40—C41178.9 (2)
C17—C18—C19—C202.5 (4)C39—C40—C41—C421.8 (4)
C18—C19—C20—C211.1 (4)C40—C41—C42—C431.2 (4)
C18—C19—C20—Br1−177.76 (18)C40—C41—C42—Br2−178.97 (18)
C19—C20—C21—C22−2.5 (4)C41—C42—C43—C44−2.2 (4)
Br1—C20—C21—C22176.43 (18)Br2—C42—C43—C44177.91 (18)
C20—C21—C22—C170.2 (4)C40—C39—C44—C432.7 (4)
C18—C17—C22—C213.4 (4)N2—C39—C44—C43−179.9 (2)
N1—C17—C22—C21−179.0 (2)C42—C43—C44—C390.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···S20.90 (2)2.11 (2)2.890 (2)146 (2)
N2—H2···S40.88 (2)2.10 (2)2.887 (2)149 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2877).

References

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  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • El Ashry, E. S. H., Amer, M. R., Raza Shah, M. & Ng, S. W. (2009). Acta Cryst. E65, o597. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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