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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1567.
Published online 2008 July 23. doi:  10.1107/S1600536808022174
PMCID: PMC2962237

3,6-Dibromo-9-(4-tert-butyl­benz­yl)-9H-carbazole

Abstract

In the title compound, C23H21Br2N, which was synthesized by the N-alkyl­ation of 1-tert-butyl-4-(chloro­meth­yl)benzene with 3,6-dibromo-9H-carbazole, the asymmetric unit contains two unique mol­ecules. Each carbazole ring system is essentially planar, with mean deviations of 0.0077 and 0.0089 Å for the two mol­ecules. The carbazole planes make dihedral angles of 78.9 (2) and 81.8 (2)° with the planes of the respective benzene rings.

Related literature

For the pharmaceutical properties of carbazole derivatives, see: Buu-Hoï & Royer (1950 [triangle]); Caulfield et al. (2002 [triangle]); Harfenist & Joyner (1983 [triangle]); Harper et al. (2002 [triangle]). For the preparation of the title compound, see: Duan et al. (2005 [triangle]); Smith et al. (1992 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1567-scheme1.jpg

Experimental

Crystal data

  • C23H21Br2N
  • M r = 471.23
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1567-efi1.jpg
  • a = 11.240 (2) Å
  • b = 12.921 (3) Å
  • c = 15.694 (3) Å
  • α = 105.43 (3)°
  • β = 108.53 (3)°
  • γ = 103.09 (3)°
  • V = 1958.9 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 4.14 mm−1
  • T = 113 (2) K
  • 0.10 × 0.08 × 0.04 mm

Data collection

  • Rigaku Saturn CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.682, T max = 0.852
  • 12085 measured reflections
  • 6891 independent reflections
  • 4712 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.112
  • S = 1.01
  • 6891 reflections
  • 475 parameters
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022174/sj2514sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022174/sj2514Isup2.hkl

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

supplementary crystallographic information

Comment

Carbazole derivatives substituted by N-alkylation possess valuable pharmaceutical properties (Buu-Hoï & Royer, 1950; Harfenist & Joyner, 1983; Caulfield et al., 2002; Harper et al., 2002). In this paper, the structure of 3,6-dibromo-9-(4-tert-butylbenzyl)-9H-carbazole, (I), which was synthesized by the N-alkylation of 1-tert-butyl-4-(chloromethyl)benzene with 3,6-dibromo-9H-carbazole is reported, Fig. 1. The compound crystallises with two unique molecules in the asymmetric unit. Each carbazole ring system is essentially planar with mean deviations of 0.0077Å and 0.0089Å for the two molecules. In each molecule, the carbazole planes and make dihedral angles of 78.9 (2)° and 81.8 (2)° with the planes of the respective benzene rings. The C—Br distances fall in the range 1.894 (6) to 1.909 (5) Å, consistent with the literature (Allen et al., 1987).

Experimental

The title compound was prepared according to the procedures of Smith et al. (1992) and Duan et al. (2005). The compound, (I) (40 mg), was dissolved in a mixture of chloroform (10 ml) and ethanol (5 ml) and the solution was kept at room temperature for 18 d. Natural evaporation of the solution gave colourless crystals suitable for X-Ray analysis (m.p. 434–435 K).

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for CH2 H atoms and C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for CH3 H atoms.

Figures

Fig. 1.
A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for H atoms).

Crystal data

C23H21Br2NZ = 4
Mr = 471.23F000 = 944
Triclinic, P1Dx = 1.598 Mg m3
Hall symbol: -P 1Melting point = 434–435 K
a = 11.240 (2) ÅMo Kα radiation λ = 0.71073 Å
b = 12.921 (3) ÅCell parameters from 3716 reflections
c = 15.694 (3) Åθ = 1.5–27.9º
α = 105.43 (3)ºµ = 4.15 mm1
β = 108.53 (3)ºT = 113 (2) K
γ = 103.09 (3)ºPrism, colorless
V = 1958.9 (10) Å30.10 × 0.08 × 0.04 mm

Data collection

Rigaku Saturn CCD diffractometer6891 independent reflections
Radiation source: rotating anode4712 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.051
T = 293(2) Kθmax = 25.0º
ω scansθmin = 1.5º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)h = −9→13
Tmin = 0.682, Tmax = 0.852k = −15→15
12085 measured reflectionsl = −18→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.112  w = 1/[σ2(Fo2) + (0.0441P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6891 reflectionsΔρmax = 0.46 e Å3
475 parametersΔρmin = −0.46 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Br10.96240 (7)0.27334 (4)1.22201 (4)0.03941 (19)
Br21.17197 (7)0.38918 (5)0.76081 (4)0.04177 (19)
Br30.40645 (7)−0.22495 (4)0.71466 (4)0.04018 (19)
Br40.72986 (7)−0.12045 (5)0.29922 (4)0.03927 (18)
N10.7041 (5)0.3752 (3)0.8695 (3)0.0221 (10)
N20.2243 (5)−0.1201 (3)0.3530 (3)0.0215 (10)
C10.7459 (6)0.3489 (4)0.9523 (3)0.0250 (13)
C20.6817 (6)0.3308 (4)1.0116 (4)0.0297 (14)
H20.59640.33450.99860.036*
C30.7475 (6)0.3070 (4)1.0907 (4)0.0288 (14)
H30.70630.29491.13180.035*
C40.8725 (7)0.3011 (4)1.1094 (3)0.0304 (15)
C50.9398 (6)0.3174 (3)1.0509 (3)0.0237 (12)
H51.02480.31271.06450.028*
C60.8735 (6)0.3410 (3)0.9708 (3)0.0216 (13)
C70.9125 (6)0.3640 (4)0.8957 (3)0.0217 (12)
C81.0244 (6)0.3672 (3)0.8753 (3)0.0240 (13)
H81.09640.35400.91460.029*
C91.0251 (6)0.3906 (4)0.7951 (4)0.0277 (14)
C100.9171 (6)0.4106 (4)0.7345 (4)0.0292 (15)
H100.92080.42570.68050.035*
C110.8074 (6)0.4081 (4)0.7545 (3)0.0254 (13)
H110.73600.42160.71500.031*
C120.8049 (6)0.3847 (3)0.8359 (3)0.0229 (13)
C130.5880 (6)0.4076 (4)0.8353 (4)0.0336 (15)
H13A0.51960.36970.85270.040*
H13B0.55290.38220.76540.040*
C140.6203 (6)0.5352 (4)0.8772 (3)0.0232 (12)
C150.6477 (6)0.6037 (4)0.8271 (3)0.0320 (15)
H150.63900.56980.76420.038*
C160.6884 (6)0.7231 (4)0.8683 (3)0.0289 (14)
H160.70700.76720.83290.035*
C170.7008 (5)0.7753 (4)0.9615 (3)0.0198 (12)
C180.6714 (6)0.7060 (4)1.0113 (4)0.0250 (13)
H180.67810.73951.07370.030*
C190.6323 (6)0.5881 (4)0.9705 (4)0.0283 (14)
H190.61410.54401.00600.034*
C200.7512 (6)0.9073 (4)1.0123 (3)0.0233 (13)
C210.7776 (7)0.9676 (4)0.9457 (4)0.0401 (17)
H21A0.81441.04870.98060.060*
H21B0.69540.94960.89200.060*
H21C0.83960.94280.92250.060*
C220.6453 (7)0.9413 (4)1.0432 (4)0.0412 (17)
H22A0.62900.90431.08600.062*
H22B0.56420.91840.98720.062*
H22C0.67631.02261.07590.062*
C230.8795 (6)0.9417 (4)1.1000 (4)0.0365 (16)
H23A0.94360.91601.08010.055*
H23B0.86200.90761.14410.055*
H23C0.91441.02331.13130.055*
C240.2497 (6)−0.1459 (3)0.4368 (3)0.0232 (13)
C250.1684 (6)−0.1601 (4)0.4870 (3)0.0267 (13)
H250.0844−0.15310.46610.032*
C260.2170 (7)−0.1848 (4)0.5688 (4)0.0312 (15)
H260.1651−0.19510.60370.037*
C270.3413 (6)−0.1944 (4)0.5992 (3)0.0242 (13)
C280.4236 (6)−0.1816 (3)0.5510 (3)0.0225 (13)
H280.5070−0.18950.57270.027*
C290.3755 (6)−0.1560 (4)0.4675 (3)0.0202 (12)
C300.4306 (6)−0.1369 (3)0.3996 (3)0.0209 (12)
C310.5495 (6)−0.1379 (4)0.3913 (3)0.0244 (13)
H310.6138−0.15280.43610.029*
C320.5699 (6)−0.1164 (4)0.3150 (4)0.0253 (13)
C330.4756 (6)−0.0936 (4)0.2466 (4)0.0267 (13)
H330.4931−0.07870.19610.032*
C340.3577 (6)−0.0931 (3)0.2537 (3)0.0257 (14)
H340.2938−0.07910.20800.031*
C350.3351 (6)−0.1141 (3)0.3311 (3)0.0185 (12)
C360.1124 (6)−0.0882 (3)0.3058 (3)0.0249 (13)
H36A0.0335−0.13030.31110.030*
H36B0.0947−0.10870.23780.030*
C370.1396 (6)0.0393 (4)0.3505 (3)0.0245 (13)
C380.2053 (6)0.1155 (4)0.3192 (3)0.0256 (13)
H380.22760.08810.26740.031*
C390.2386 (6)0.2327 (4)0.3642 (3)0.0268 (13)
H390.28270.28210.34180.032*
C400.2080 (5)0.2775 (4)0.4414 (3)0.0188 (11)
C410.1410 (6)0.1999 (4)0.4720 (3)0.0266 (13)
H410.11890.22700.52400.032*
C420.1066 (6)0.0831 (4)0.4264 (4)0.0281 (13)
H420.06020.03340.44750.034*
C430.2505 (6)0.4068 (4)0.4975 (3)0.0218 (12)
C440.1313 (6)0.4382 (4)0.5087 (4)0.0309 (14)
H44A0.09540.39540.54170.046*
H44B0.06390.42040.44600.046*
H44C0.16000.51830.54530.046*
C450.3586 (6)0.4352 (4)0.5971 (3)0.0304 (14)
H45A0.32350.39190.63000.046*
H45B0.38660.51530.63390.046*
H45C0.43350.41640.58970.046*
C460.3061 (6)0.4770 (4)0.4454 (4)0.0323 (15)
H46A0.33310.55690.48230.048*
H46B0.23850.45890.38270.048*
H46C0.38170.45920.43840.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0530 (5)0.0296 (3)0.0276 (3)0.0098 (3)0.0069 (3)0.0133 (2)
Br20.0489 (5)0.0399 (3)0.0429 (3)0.0163 (3)0.0301 (4)0.0095 (3)
Br30.0521 (5)0.0372 (3)0.0297 (3)0.0113 (3)0.0126 (3)0.0177 (2)
Br40.0338 (5)0.0463 (3)0.0379 (3)0.0149 (3)0.0215 (3)0.0062 (3)
N10.014 (3)0.0200 (19)0.025 (2)0.007 (2)−0.001 (2)0.0091 (17)
N20.023 (3)0.0172 (19)0.028 (2)0.011 (2)0.007 (2)0.0121 (17)
C10.033 (4)0.012 (2)0.030 (3)0.010 (3)0.012 (3)0.005 (2)
C20.031 (4)0.018 (2)0.037 (3)0.007 (3)0.013 (3)0.009 (2)
C30.030 (4)0.024 (2)0.032 (3)0.007 (3)0.015 (3)0.008 (2)
C40.044 (5)0.016 (2)0.024 (3)0.005 (3)0.010 (3)0.005 (2)
C50.021 (4)0.015 (2)0.028 (3)0.007 (2)0.004 (3)0.004 (2)
C60.025 (4)0.010 (2)0.021 (2)0.005 (2)0.004 (3)0.0003 (19)
C70.024 (4)0.013 (2)0.021 (2)0.006 (2)0.003 (3)0.0018 (19)
C80.026 (4)0.015 (2)0.023 (3)0.006 (2)0.005 (3)0.001 (2)
C90.036 (4)0.015 (2)0.030 (3)0.006 (3)0.018 (3)0.003 (2)
C100.045 (5)0.016 (2)0.026 (3)0.005 (3)0.018 (3)0.007 (2)
C110.023 (4)0.019 (2)0.022 (3)0.001 (2)−0.001 (3)0.007 (2)
C120.029 (4)0.012 (2)0.026 (3)0.005 (2)0.013 (3)0.002 (2)
C130.030 (4)0.025 (3)0.034 (3)0.007 (3)0.002 (3)0.009 (2)
C140.012 (4)0.022 (2)0.026 (3)0.005 (2)−0.001 (3)0.005 (2)
C150.046 (5)0.026 (3)0.023 (3)0.022 (3)0.009 (3)0.008 (2)
C160.035 (4)0.028 (3)0.022 (3)0.012 (3)0.003 (3)0.015 (2)
C170.012 (3)0.020 (2)0.023 (2)0.005 (2)0.003 (3)0.007 (2)
C180.025 (4)0.027 (3)0.027 (3)0.011 (3)0.015 (3)0.009 (2)
C190.032 (4)0.024 (2)0.038 (3)0.013 (3)0.020 (3)0.016 (2)
C200.023 (4)0.018 (2)0.021 (2)0.004 (2)0.003 (3)0.003 (2)
C210.063 (6)0.019 (2)0.034 (3)0.009 (3)0.019 (4)0.009 (2)
C220.048 (5)0.031 (3)0.049 (4)0.017 (3)0.024 (4)0.012 (3)
C230.036 (5)0.024 (3)0.034 (3)−0.001 (3)0.007 (3)0.004 (2)
C240.026 (4)0.012 (2)0.019 (2)0.000 (2)0.001 (3)0.0006 (19)
C250.022 (4)0.022 (2)0.028 (3)0.005 (2)0.006 (3)0.005 (2)
C260.039 (5)0.025 (3)0.032 (3)0.008 (3)0.020 (3)0.010 (2)
C270.023 (4)0.017 (2)0.028 (3)0.002 (2)0.007 (3)0.008 (2)
C280.022 (4)0.015 (2)0.023 (2)0.005 (2)0.004 (3)0.003 (2)
C290.019 (4)0.015 (2)0.019 (2)0.004 (2)0.004 (3)0.0010 (19)
C300.026 (4)0.012 (2)0.024 (3)0.006 (2)0.012 (3)0.0015 (19)
C310.028 (4)0.019 (2)0.021 (2)0.007 (2)0.006 (3)0.004 (2)
C320.025 (4)0.014 (2)0.030 (3)0.003 (2)0.013 (3)−0.002 (2)
C330.028 (4)0.020 (2)0.030 (3)0.002 (3)0.014 (3)0.006 (2)
C340.034 (4)0.016 (2)0.022 (3)0.004 (3)0.010 (3)0.007 (2)
C350.020 (4)0.011 (2)0.020 (2)0.007 (2)0.006 (3)0.0008 (19)
C360.027 (4)0.016 (2)0.026 (3)0.007 (2)0.009 (3)0.002 (2)
C370.024 (4)0.026 (2)0.023 (3)0.012 (3)0.006 (3)0.009 (2)
C380.032 (4)0.031 (3)0.021 (2)0.017 (3)0.014 (3)0.012 (2)
C390.036 (4)0.024 (2)0.030 (3)0.014 (3)0.016 (3)0.017 (2)
C400.009 (3)0.023 (2)0.014 (2)0.006 (2)−0.005 (2)0.0032 (19)
C410.027 (4)0.029 (3)0.026 (3)0.010 (3)0.012 (3)0.011 (2)
C420.024 (4)0.022 (2)0.041 (3)0.005 (3)0.016 (3)0.013 (2)
C430.019 (4)0.021 (2)0.023 (2)0.005 (2)0.009 (3)0.005 (2)
C440.036 (5)0.026 (3)0.031 (3)0.013 (3)0.015 (3)0.007 (2)
C450.032 (4)0.027 (3)0.027 (3)0.008 (3)0.008 (3)0.009 (2)
C460.042 (5)0.022 (2)0.033 (3)0.013 (3)0.015 (3)0.010 (2)

Geometric parameters (Å, °)

Br1—C41.908 (5)C22—H22B0.9600
Br2—C91.894 (6)C22—H22C0.9600
Br3—C271.909 (5)C23—H23A0.9600
Br4—C321.901 (6)C23—H23B0.9600
N1—C121.388 (7)C23—H23C0.9600
N1—C11.395 (6)C24—C291.391 (8)
N1—C131.445 (7)C24—C251.397 (7)
N2—C351.384 (6)C25—C261.379 (7)
N2—C241.399 (6)C25—H250.9300
N2—C361.452 (7)C26—C271.372 (8)
C1—C21.381 (7)C26—H260.9300
C1—C61.403 (8)C27—C281.377 (7)
C2—C31.380 (7)C28—C291.408 (6)
C2—H20.9300C28—H280.9300
C3—C41.366 (8)C29—C301.438 (6)
C3—H30.9300C30—C311.386 (7)
C4—C51.390 (7)C30—C351.406 (7)
C5—C61.393 (7)C31—C321.374 (6)
C5—H50.9300C31—H310.9300
C6—C71.457 (6)C32—C331.396 (8)
C7—C81.388 (7)C33—C341.367 (8)
C7—C121.405 (8)C33—H330.9300
C8—C91.372 (6)C34—C351.398 (6)
C8—H80.9300C34—H340.9300
C9—C101.409 (8)C36—C371.522 (6)
C10—C111.362 (8)C36—H36A0.9700
C10—H100.9300C36—H36B0.9700
C11—C121.396 (6)C37—C421.377 (6)
C11—H110.9300C37—C381.384 (6)
C13—C141.512 (6)C38—C391.392 (6)
C13—H13A0.9700C38—H380.9300
C13—H13B0.9700C39—C401.379 (6)
C14—C151.376 (6)C39—H390.9300
C14—C191.389 (6)C40—C411.396 (6)
C15—C161.403 (6)C40—C431.544 (6)
C15—H150.9300C41—C421.387 (6)
C16—C171.385 (6)C41—H410.9300
C16—H160.9300C42—H420.9300
C17—C181.386 (6)C43—C451.529 (7)
C17—C201.554 (6)C43—C441.531 (7)
C18—C191.387 (6)C43—C461.531 (6)
C18—H180.9300C44—H44A0.9600
C19—H190.9300C44—H44B0.9600
C20—C231.515 (8)C44—H44C0.9600
C20—C211.521 (6)C45—H45A0.9600
C20—C221.529 (8)C45—H45B0.9600
C21—H21A0.9600C45—H45C0.9600
C21—H21B0.9600C46—H46A0.9600
C21—H21C0.9600C46—H46B0.9600
C22—H22A0.9600C46—H46C0.9600
C12—N1—C1108.1 (5)C20—C23—H23C109.5
C12—N1—C13125.4 (4)H23A—C23—H23C109.5
C1—N1—C13125.6 (5)H23B—C23—H23C109.5
C35—N2—C24107.4 (5)C29—C24—C25121.7 (5)
C35—N2—C36125.4 (4)C29—C24—N2109.5 (4)
C24—N2—C36126.5 (4)C25—C24—N2128.8 (6)
C2—C1—N1130.2 (6)C26—C25—C24117.6 (6)
C2—C1—C6121.0 (5)C26—C25—H25121.2
N1—C1—C6108.8 (4)C24—C25—H25121.2
C3—C2—C1118.2 (6)C27—C26—C25120.6 (5)
C3—C2—H2120.9C27—C26—H26119.7
C1—C2—H2120.9C25—C26—H26119.7
C4—C3—C2120.7 (5)C26—C27—C28123.2 (5)
C4—C3—H3119.6C26—C27—Br3119.2 (4)
C2—C3—H3119.6C28—C27—Br3117.6 (4)
C3—C4—C5122.8 (5)C27—C28—C29116.9 (5)
C3—C4—Br1119.4 (4)C27—C28—H28121.5
C5—C4—Br1117.8 (5)C29—C28—H28121.5
C4—C5—C6116.6 (6)C24—C29—C28119.9 (5)
C4—C5—H5121.7C24—C29—C30107.0 (4)
C6—C5—H5121.7C28—C29—C30133.0 (5)
C5—C6—C1120.7 (5)C31—C30—C35119.9 (4)
C5—C6—C7131.9 (5)C31—C30—C29133.6 (5)
C1—C6—C7107.4 (4)C35—C30—C29106.5 (5)
C8—C7—C12120.5 (4)C32—C31—C30118.2 (5)
C8—C7—C6134.0 (5)C32—C31—H31120.9
C12—C7—C6105.5 (5)C30—C31—H31120.9
C9—C8—C7117.6 (5)C31—C32—C33122.3 (5)
C9—C8—H8121.2C31—C32—Br4119.5 (4)
C7—C8—H8121.2C33—C32—Br4118.2 (4)
C8—C9—C10122.1 (5)C34—C33—C32120.0 (5)
C8—C9—Br2119.3 (5)C34—C33—H33120.0
C10—C9—Br2118.5 (4)C32—C33—H33120.0
C11—C10—C9120.4 (5)C33—C34—C35118.7 (5)
C11—C10—H10119.8C33—C34—H34120.7
C9—C10—H10119.8C35—C34—H34120.7
C10—C11—C12118.3 (5)N2—C35—C34129.6 (5)
C10—C11—H11120.8N2—C35—C30109.5 (4)
C12—C11—H11120.8C34—C35—C30120.9 (5)
N1—C12—C11128.8 (5)N2—C36—C37111.7 (4)
N1—C12—C7110.2 (4)N2—C36—H36A109.3
C11—C12—C7121.0 (5)C37—C36—H36A109.3
N1—C13—C14111.9 (5)N2—C36—H36B109.3
N1—C13—H13A109.2C37—C36—H36B109.3
C14—C13—H13A109.2H36A—C36—H36B107.9
N1—C13—H13B109.2C42—C37—C38117.8 (4)
C14—C13—H13B109.2C42—C37—C36121.4 (4)
H13A—C13—H13B107.9C38—C37—C36120.7 (4)
C15—C14—C19117.8 (4)C37—C38—C39120.9 (4)
C15—C14—C13121.3 (4)C37—C38—H38119.6
C19—C14—C13120.7 (4)C39—C38—H38119.6
C14—C15—C16121.9 (4)C40—C39—C38121.7 (4)
C14—C15—H15119.1C40—C39—H39119.1
C16—C15—H15119.1C38—C39—H39119.1
C17—C16—C15120.1 (4)C39—C40—C41116.9 (4)
C17—C16—H16120.0C39—C40—C43123.5 (4)
C15—C16—H16120.0C41—C40—C43119.4 (4)
C16—C17—C18117.9 (4)C42—C41—C40121.3 (4)
C16—C17—C20122.3 (4)C42—C41—H41119.4
C18—C17—C20119.8 (4)C40—C41—H41119.4
C17—C18—C19121.8 (4)C37—C42—C41121.3 (4)
C17—C18—H18119.1C37—C42—H42119.3
C19—C18—H18119.1C41—C42—H42119.3
C18—C19—C14120.6 (4)C45—C43—C44109.8 (4)
C18—C19—H19119.7C45—C43—C46109.4 (4)
C14—C19—H19119.7C44—C43—C46108.2 (4)
C23—C20—C21109.3 (5)C45—C43—C40107.6 (4)
C23—C20—C22110.1 (4)C44—C43—C40110.5 (4)
C21—C20—C22109.0 (4)C46—C43—C40111.3 (4)
C23—C20—C17108.0 (4)C43—C44—H44A109.5
C21—C20—C17111.7 (4)C43—C44—H44B109.5
C22—C20—C17108.8 (4)H44A—C44—H44B109.5
C20—C21—H21A109.5C43—C44—H44C109.5
C20—C21—H21B109.5H44A—C44—H44C109.5
H21A—C21—H21B109.5H44B—C44—H44C109.5
C20—C21—H21C109.5C43—C45—H45A109.5
H21A—C21—H21C109.5C43—C45—H45B109.5
H21B—C21—H21C109.5H45A—C45—H45B109.5
C20—C22—H22A109.5C43—C45—H45C109.5
C20—C22—H22B109.5H45A—C45—H45C109.5
H22A—C22—H22B109.5H45B—C45—H45C109.5
C20—C22—H22C109.5C43—C46—H46A109.5
H22A—C22—H22C109.5C43—C46—H46B109.5
H22B—C22—H22C109.5H46A—C46—H46B109.5
C20—C23—H23A109.5C43—C46—H46C109.5
C20—C23—H23B109.5H46A—C46—H46C109.5
H23A—C23—H23B109.5H46B—C46—H46C109.5
C12—N1—C1—C2−179.9 (4)C35—N2—C24—C290.0 (5)
C13—N1—C1—C210.5 (8)C36—N2—C24—C29−171.3 (4)
C12—N1—C1—C6−0.3 (5)C35—N2—C24—C25179.6 (4)
C13—N1—C1—C6−169.9 (4)C36—N2—C24—C258.3 (7)
N1—C1—C2—C3−179.2 (5)C29—C24—C25—C26−0.1 (7)
C6—C1—C2—C31.3 (7)N2—C24—C25—C26−179.6 (4)
C1—C2—C3—C4−0.3 (7)C24—C25—C26—C270.3 (7)
C2—C3—C4—C5−0.5 (8)C25—C26—C27—C28−0.7 (8)
C2—C3—C4—Br1177.8 (3)C25—C26—C27—Br3178.4 (3)
C3—C4—C5—C60.3 (7)C26—C27—C28—C290.8 (7)
Br1—C4—C5—C6−178.1 (3)Br3—C27—C28—C29−178.3 (3)
C4—C5—C6—C10.7 (6)C25—C24—C29—C280.2 (7)
C4—C5—C6—C7179.1 (4)N2—C24—C29—C28179.9 (4)
C2—C1—C6—C5−1.5 (7)C25—C24—C29—C30179.8 (4)
N1—C1—C6—C5178.9 (4)N2—C24—C29—C30−0.6 (5)
C2—C1—C6—C7179.7 (4)C27—C28—C29—C24−0.6 (6)
N1—C1—C6—C70.1 (5)C27—C28—C29—C30−180.0 (4)
C5—C6—C7—C82.2 (8)C24—C29—C30—C31−178.7 (5)
C1—C6—C7—C8−179.2 (5)C28—C29—C30—C310.8 (9)
C5—C6—C7—C12−178.5 (5)C24—C29—C30—C350.9 (5)
C1—C6—C7—C120.1 (5)C28—C29—C30—C35−179.6 (5)
C12—C7—C8—C9−0.3 (6)C35—C30—C31—C32−0.1 (6)
C6—C7—C8—C9178.9 (4)C29—C30—C31—C32179.5 (4)
C7—C8—C9—C10−0.1 (7)C30—C31—C32—C330.1 (7)
C7—C8—C9—Br2−177.2 (3)C30—C31—C32—Br4−178.5 (3)
C8—C9—C10—C110.5 (7)C31—C32—C33—C34−0.5 (7)
Br2—C9—C10—C11177.5 (3)Br4—C32—C33—C34178.1 (3)
C9—C10—C11—C12−0.3 (7)C32—C33—C34—C350.9 (7)
C1—N1—C12—C11178.9 (4)C24—N2—C35—C34178.6 (4)
C13—N1—C12—C11−11.5 (7)C36—N2—C35—C34−9.9 (7)
C1—N1—C12—C70.4 (5)C24—N2—C35—C300.6 (5)
C13—N1—C12—C7170.0 (4)C36—N2—C35—C30172.0 (4)
C10—C11—C12—N1−178.5 (4)C33—C34—C35—N2−178.7 (4)
C10—C11—C12—C7−0.1 (7)C33—C34—C35—C30−0.9 (6)
C8—C7—C12—N1179.1 (4)C31—C30—C35—N2178.7 (4)
C6—C7—C12—N1−0.3 (5)C29—C30—C35—N2−0.9 (5)
C8—C7—C12—C110.5 (7)C31—C30—C35—C340.5 (7)
C6—C7—C12—C11−179.0 (4)C29—C30—C35—C34−179.2 (4)
C12—N1—C13—C14−78.4 (6)C35—N2—C36—C37−84.9 (5)
C1—N1—C13—C1489.4 (6)C24—N2—C36—C3785.0 (6)
N1—C13—C14—C1596.5 (6)N2—C36—C37—C42−90.0 (6)
N1—C13—C14—C19−78.9 (7)N2—C36—C37—C3886.4 (6)
C19—C14—C15—C160.8 (9)C42—C37—C38—C391.0 (8)
C13—C14—C15—C16−174.7 (6)C36—C37—C38—C39−175.5 (5)
C14—C15—C16—C17−0.6 (9)C37—C38—C39—C400.0 (9)
C15—C16—C17—C18−0.2 (9)C38—C39—C40—C41−0.4 (8)
C15—C16—C17—C20177.3 (5)C38—C39—C40—C43176.1 (5)
C16—C17—C18—C190.8 (9)C39—C40—C41—C42−0.3 (8)
C20—C17—C18—C19−176.8 (5)C43—C40—C41—C42−176.9 (5)
C17—C18—C19—C14−0.5 (9)C38—C37—C42—C41−1.7 (9)
C15—C14—C19—C18−0.3 (9)C36—C37—C42—C41174.8 (5)
C13—C14—C19—C18175.3 (5)C40—C41—C42—C371.4 (9)
C16—C17—C20—C23−117.6 (6)C39—C40—C43—C45−109.0 (6)
C18—C17—C20—C2359.8 (6)C41—C40—C43—C4567.4 (6)
C16—C17—C20—C212.6 (8)C39—C40—C43—C44131.1 (5)
C18—C17—C20—C21−180.0 (5)C41—C40—C43—C44−52.5 (6)
C16—C17—C20—C22122.9 (6)C39—C40—C43—C4610.8 (7)
C18—C17—C20—C22−59.7 (6)C41—C40—C43—C46−172.8 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2514).

References

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