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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o216.
Published online 2009 January 8. doi:  10.1107/S1600536808042827
PMCID: PMC2968375

3,6-Dibromo-9-(4-bromo­benz­yl)-9H-carbazole

Abstract

The title compound, C19H12Br3N, was synthesized by N-alkyl­ation of 1-bromo-4-(bromo­meth­yl)benzene with 3,6-dibromo-9H-carbazole. There are two unique mol­ecules in the asymmetric unit. The carbazole ring system is essentially planar, with a mean deviation of 0.0402 Å for one mol­ecule and 0.0279 Å for the other. The carbazole planes are inclined to the benzene ring planes at dihedral angles of 58.3 (3) and 71.1 (3)° in the two mol­ecules.

Related literature

For the pharmaceutical properties of carbazoles, see: Buu-Hoï & Royer (1950 [triangle]); Caulfield et al. (2002 [triangle]); Harfenist & Joyner (1983 [triangle]); Harper et al. (2002 [triangle]). For bond length data, see: Allen et al. (1987 [triangle]). For the synthesis of the title compound, see: Duan et al. (2005a [triangle],b [triangle]); Smith et al. (1992 [triangle]). For related literature, see: Borzatta & Carrozza (1991 [triangle]). For a related structure, see: Cui et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o216-scheme1.jpg

Experimental

Crystal data

  • C19H12Br3N
  • M r = 494.00
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o216-efi1.jpg
  • a = 9.4784 (19) Å
  • b = 17.132 (3) Å
  • c = 20.456 (4) Å
  • β = 98.16 (3)°
  • V = 3288.1 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 7.36 mm−1
  • T = 113 (2) K
  • 0.08 × 0.02 × 0.02 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.591, T max = 0.867
  • 25134 measured reflections
  • 7824 independent reflections
  • 6058 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.103
  • S = 1.02
  • 7824 reflections
  • 415 parameters
  • H-atom parameters constrained
  • Δρmax = 0.62 e Å−3
  • Δρmin = −0.86 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/S1600536808042827/sj2546sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042827/sj2546Isup2.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, we report the structure of 3,6-dibromo-9-(4-bromobenzyl)-9H-carbazole (I), which was synthesized by N-alkylation of 1-bromo-4-(bromomethyl)benzene with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar with mean deviations of 0.0402Å for one molecule and 0.0279 Å for the other. The carbazole planes are inclined to the benzene ring planes at dihedral angles of 58.3 (3)° and 108.9 (3) ° respectively. The C—Br distances fall in the range 1.894 (6) to 1.911 (5) Å, consistent with the literature (Allen et al., 1987).

Experimental

The title compound was prepared according to the procedure of Duan et al. (2005a,b) from 3,6-dibromo-carbazole (Smith et al. 1992) and 1-bromo-4-(bromomethyl)benzene. Compound (I) (40 mg) was dissolved in 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. 480–481 K).

Refinement

All H atoms were included in the riding model approximation with C—H distances = 0.93 (aromatic) and 0.97 (methylene) Å, and with Uiso(H) = 1.2xUeq(C).

Figures

Fig. 1.
The asymmetric unit of (I) with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C19H12Br3NF(000) = 1904
Mr = 494.00Dx = 1.996 Mg m3
Monoclinic, P21/nMelting point = 480–481 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.4784 (19) ÅCell parameters from 6869 reflections
b = 17.132 (3) Åθ = 1.6–28.0°
c = 20.456 (4) ŵ = 7.36 mm1
β = 98.16 (3)°T = 113 K
V = 3288.1 (11) Å3Prism, colorless
Z = 80.08 × 0.02 × 0.02 mm

Data collection

Rigaku Saturn diffractometer7824 independent reflections
Radiation source: rotating anode6058 reflections with I > 2σ(I)
confocalRint = 0.054
ω scansθmax = 27.9°, θmin = 1.6°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)h = −12→10
Tmin = 0.591, Tmax = 0.867k = −20→22
25134 measured reflectionsl = −26→26

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
7824 reflections(Δ/σ)max = 0.002
415 parametersΔρmax = 0.62 e Å3
0 restraintsΔρmin = −0.86 e Å3

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
Br1−0.14151 (4)0.08974 (2)0.20844 (2)0.02780 (12)
Br20.26336 (5)0.39468 (3)0.51841 (2)0.03025 (12)
Br30.10307 (5)0.67522 (3)0.01113 (2)0.02914 (12)
Br40.36237 (4)0.08294 (2)0.17850 (2)0.02334 (11)
Br50.71818 (6)0.37880 (3)0.50564 (2)0.03361 (13)
Br60.57775 (5)0.68767 (2)0.03165 (2)0.02995 (12)
N10.2671 (3)0.36064 (19)0.22607 (17)0.0202 (7)
N20.7685 (3)0.35444 (19)0.21649 (16)0.0191 (7)
C10.1733 (4)0.2987 (2)0.2121 (2)0.0185 (8)
C20.1328 (4)0.2593 (2)0.1533 (2)0.0209 (9)
H20.16830.27370.11500.025*
C30.0377 (4)0.1977 (2)0.1532 (2)0.0226 (9)
H30.00970.16980.11450.027*
C4−0.0161 (4)0.1774 (2)0.2112 (2)0.0228 (9)
C50.0207 (4)0.2165 (2)0.2699 (2)0.0218 (9)
H5−0.01780.20250.30760.026*
C60.1174 (4)0.2777 (2)0.2708 (2)0.0198 (9)
C70.1859 (4)0.3280 (2)0.3219 (2)0.0192 (8)
C80.1804 (4)0.3334 (2)0.3900 (2)0.0204 (9)
H80.12030.30140.41040.024*
C90.2673 (5)0.3878 (2)0.4256 (2)0.0229 (9)
C100.3593 (4)0.4368 (2)0.3975 (2)0.0214 (9)
H100.41610.47230.42370.026*
C110.3660 (4)0.4324 (2)0.3301 (2)0.0204 (9)
H110.42660.46460.31030.025*
C120.2786 (4)0.3777 (2)0.2932 (2)0.0181 (8)
C130.3542 (4)0.3943 (2)0.1802 (2)0.0197 (9)
H13A0.37580.35380.15000.024*
H13B0.44370.41150.20500.024*
C140.2862 (4)0.4627 (2)0.1401 (2)0.0202 (9)
C150.2893 (4)0.5380 (2)0.1667 (2)0.0223 (9)
H150.32930.54610.21030.027*
C160.2335 (4)0.6010 (2)0.1286 (2)0.0228 (9)
H160.23490.65080.14660.027*
C170.1758 (4)0.5882 (2)0.0636 (2)0.0205 (9)
C180.1704 (4)0.5147 (2)0.0362 (2)0.0217 (9)
H180.13080.5071−0.00760.026*
C190.2245 (4)0.4523 (2)0.0745 (2)0.0204 (9)
H190.21980.40240.05640.024*
C200.6758 (4)0.2931 (2)0.1978 (2)0.0175 (8)
C210.6408 (4)0.2566 (2)0.1368 (2)0.0187 (8)
H210.68080.27320.10030.022*
C220.5455 (4)0.1955 (2)0.1317 (2)0.0195 (8)
H220.52140.16990.09160.023*
C230.4851 (4)0.1720 (2)0.1870 (2)0.0202 (9)
C240.5139 (4)0.2079 (2)0.2474 (2)0.0195 (8)
H240.47040.19180.28310.023*
C250.6115 (4)0.2698 (2)0.25318 (19)0.0169 (8)
C260.6708 (4)0.3185 (2)0.3077 (2)0.0202 (9)
C270.6534 (5)0.3220 (2)0.3746 (2)0.0224 (9)
H270.58880.28950.39170.027*
C280.7347 (4)0.3749 (2)0.4143 (2)0.0225 (9)
C290.8310 (5)0.4252 (2)0.3896 (2)0.0253 (10)
H290.88390.46010.41800.030*
C300.8487 (4)0.4238 (2)0.3237 (2)0.0240 (9)
H300.91190.45750.30720.029*
C310.7682 (4)0.3698 (2)0.2827 (2)0.0192 (8)
C320.8553 (4)0.3959 (2)0.1744 (2)0.0214 (9)
H32A0.87690.36090.13990.026*
H32B0.94480.41060.20060.026*
C330.7844 (4)0.4684 (2)0.14287 (19)0.0191 (8)
C340.8599 (5)0.5385 (2)0.1439 (2)0.0239 (9)
H340.95240.54110.16610.029*
C350.7984 (5)0.6039 (2)0.1124 (2)0.0256 (10)
H350.84910.65050.11350.031*
C360.6604 (4)0.5997 (2)0.0790 (2)0.0218 (9)
C370.5819 (4)0.5316 (2)0.0782 (2)0.0219 (9)
H370.48840.52980.05700.026*
C380.6452 (4)0.4661 (2)0.1096 (2)0.0217 (9)
H380.59390.41980.10850.026*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0208 (2)0.0208 (2)0.0402 (3)−0.00171 (17)−0.00107 (19)0.00121 (19)
Br20.0424 (3)0.0291 (3)0.0198 (2)0.0031 (2)0.0065 (2)0.00106 (18)
Br30.0335 (2)0.0247 (2)0.0277 (2)0.00291 (18)−0.0008 (2)0.00693 (19)
Br40.0224 (2)0.0197 (2)0.0266 (2)−0.00224 (16)−0.00116 (18)0.00099 (17)
Br50.0505 (3)0.0309 (3)0.0183 (2)0.0093 (2)0.0009 (2)−0.00347 (19)
Br60.0369 (3)0.0202 (2)0.0314 (3)0.00635 (18)0.0000 (2)0.00390 (19)
N10.0176 (16)0.0219 (18)0.0208 (18)−0.0027 (14)0.0016 (14)0.0009 (15)
N20.0230 (17)0.0165 (17)0.0172 (17)−0.0009 (14)0.0005 (15)−0.0007 (14)
C10.0189 (19)0.0113 (19)0.025 (2)0.0029 (15)0.0014 (17)0.0007 (17)
C20.020 (2)0.021 (2)0.021 (2)0.0048 (17)−0.0010 (17)0.0020 (17)
C30.019 (2)0.021 (2)0.025 (2)0.0010 (17)−0.0058 (18)−0.0044 (18)
C40.021 (2)0.017 (2)0.029 (2)0.0033 (17)−0.0019 (18)0.0031 (18)
C50.019 (2)0.018 (2)0.027 (2)0.0041 (16)0.0004 (18)0.0041 (18)
C60.0169 (19)0.021 (2)0.022 (2)0.0040 (16)0.0018 (17)0.0057 (17)
C70.0160 (19)0.016 (2)0.025 (2)0.0037 (16)0.0015 (17)0.0015 (17)
C80.023 (2)0.019 (2)0.019 (2)0.0013 (17)0.0017 (17)0.0035 (17)
C90.030 (2)0.021 (2)0.017 (2)0.0076 (18)0.0002 (18)0.0029 (17)
C100.027 (2)0.016 (2)0.021 (2)0.0080 (17)0.0002 (18)−0.0014 (17)
C110.022 (2)0.016 (2)0.022 (2)0.0065 (16)0.0002 (18)0.0024 (17)
C120.0196 (19)0.017 (2)0.017 (2)0.0086 (16)−0.0009 (16)0.0050 (16)
C130.0184 (19)0.021 (2)0.020 (2)0.0002 (16)0.0052 (17)−0.0009 (17)
C140.018 (2)0.021 (2)0.021 (2)−0.0001 (16)0.0032 (17)0.0038 (17)
C150.024 (2)0.028 (2)0.014 (2)−0.0019 (18)0.0016 (17)−0.0034 (18)
C160.024 (2)0.018 (2)0.027 (2)−0.0012 (17)0.0052 (19)−0.0030 (18)
C170.020 (2)0.021 (2)0.020 (2)−0.0014 (17)0.0027 (17)0.0016 (17)
C180.020 (2)0.029 (2)0.015 (2)−0.0055 (17)−0.0019 (17)−0.0013 (18)
C190.0183 (19)0.020 (2)0.023 (2)−0.0026 (16)0.0048 (17)0.0007 (17)
C200.0151 (18)0.016 (2)0.020 (2)0.0031 (15)−0.0020 (16)−0.0016 (16)
C210.021 (2)0.018 (2)0.017 (2)0.0033 (16)0.0025 (17)0.0012 (16)
C220.022 (2)0.019 (2)0.017 (2)0.0020 (16)0.0012 (17)−0.0016 (16)
C230.020 (2)0.016 (2)0.023 (2)0.0023 (16)−0.0022 (17)0.0046 (17)
C240.025 (2)0.016 (2)0.018 (2)0.0015 (17)0.0036 (17)0.0014 (16)
C250.0188 (19)0.016 (2)0.0150 (19)0.0045 (15)−0.0008 (16)0.0033 (16)
C260.024 (2)0.018 (2)0.018 (2)0.0071 (17)0.0010 (17)0.0048 (17)
C270.027 (2)0.019 (2)0.020 (2)0.0053 (17)0.0023 (18)0.0021 (17)
C280.028 (2)0.023 (2)0.016 (2)0.0100 (18)−0.0016 (18)0.0012 (17)
C290.028 (2)0.017 (2)0.028 (2)0.0042 (18)−0.005 (2)−0.0080 (18)
C300.024 (2)0.019 (2)0.028 (2)0.0024 (17)0.0005 (19)−0.0009 (18)
C310.0168 (19)0.015 (2)0.025 (2)0.0070 (16)−0.0004 (17)0.0025 (17)
C320.020 (2)0.020 (2)0.026 (2)0.0001 (16)0.0059 (18)0.0031 (18)
C330.021 (2)0.020 (2)0.015 (2)0.0045 (16)−0.0016 (16)0.0012 (16)
C340.024 (2)0.022 (2)0.024 (2)−0.0034 (17)−0.0001 (18)−0.0021 (18)
C350.032 (2)0.018 (2)0.026 (2)−0.0057 (18)0.001 (2)−0.0025 (18)
C360.023 (2)0.021 (2)0.022 (2)0.0050 (17)0.0049 (18)0.0012 (17)
C370.020 (2)0.025 (2)0.021 (2)0.0013 (17)0.0038 (17)0.0027 (18)
C380.021 (2)0.021 (2)0.024 (2)−0.0040 (17)0.0058 (18)0.0036 (18)

Geometric parameters (Å, °)

Br1—C41.911 (4)C16—C171.381 (6)
Br2—C91.908 (4)C16—H160.9300
Br3—C171.907 (4)C17—C181.377 (5)
Br4—C231.911 (4)C18—C191.381 (6)
Br5—C281.899 (4)C18—H180.9300
Br6—C361.900 (4)C19—H190.9300
N1—C11.387 (5)C20—C211.392 (5)
N1—C121.394 (5)C20—C251.418 (5)
N1—C131.454 (5)C21—C221.377 (5)
N2—C311.380 (5)C21—H210.9300
N2—C201.389 (5)C22—C231.397 (5)
N2—C321.457 (5)C22—H220.9300
C1—C21.385 (6)C23—C241.373 (6)
C1—C61.426 (5)C24—C251.401 (5)
C2—C31.387 (5)C24—H240.9300
C2—H20.9300C25—C261.442 (6)
C3—C41.400 (6)C26—C271.403 (6)
C3—H30.9300C26—C311.422 (5)
C4—C51.375 (6)C27—C281.377 (6)
C5—C61.392 (6)C27—H270.9300
C5—H50.9300C28—C291.400 (6)
C6—C71.436 (6)C29—C301.382 (6)
C7—C81.404 (5)C29—H290.9300
C7—C121.410 (5)C30—C311.400 (6)
C8—C91.382 (6)C30—H300.9300
C8—H80.9300C32—C331.512 (5)
C9—C101.392 (6)C32—H32A0.9700
C10—C111.391 (6)C32—H32B0.9700
C10—H100.9300C33—C381.396 (6)
C11—C121.398 (6)C33—C341.396 (5)
C11—H110.9300C34—C351.381 (6)
C13—C141.521 (5)C34—H340.9300
C13—H13A0.9700C35—C361.389 (6)
C13—H13B0.9700C35—H350.9300
C14—C191.397 (6)C36—C371.382 (5)
C14—C151.399 (6)C37—C381.387 (6)
C15—C161.390 (6)C37—H370.9300
C15—H150.9300C38—H380.9300
C1—N1—C12108.8 (3)C18—C19—C14121.1 (4)
C1—N1—C13125.2 (3)C18—C19—H19119.4
C12—N1—C13125.5 (3)C14—C19—H19119.4
C31—N2—C20109.0 (3)N2—C20—C21130.3 (4)
C31—N2—C32124.5 (3)N2—C20—C25108.7 (3)
C20—N2—C32126.5 (3)C21—C20—C25121.0 (4)
C2—C1—N1129.9 (4)C22—C21—C20118.7 (4)
C2—C1—C6121.2 (4)C22—C21—H21120.7
N1—C1—C6108.9 (4)C20—C21—H21120.7
C1—C2—C3118.2 (4)C21—C22—C23119.8 (4)
C1—C2—H2120.9C21—C22—H22120.1
C3—C2—H2120.9C23—C22—H22120.1
C2—C3—C4120.1 (4)C24—C23—C22123.2 (4)
C2—C3—H3119.9C24—C23—Br4118.7 (3)
C4—C3—H3119.9C22—C23—Br4118.0 (3)
C5—C4—C3122.8 (4)C23—C24—C25117.3 (4)
C5—C4—Br1119.2 (3)C23—C24—H24121.3
C3—C4—Br1118.0 (3)C25—C24—H24121.3
C4—C5—C6117.7 (4)C24—C25—C20120.0 (4)
C4—C5—H5121.2C24—C25—C26133.1 (4)
C6—C5—H5121.2C20—C25—C26106.9 (3)
C5—C6—C1120.1 (4)C27—C26—C31119.9 (4)
C5—C6—C7133.8 (4)C27—C26—C25133.8 (4)
C1—C6—C7106.1 (3)C31—C26—C25106.3 (3)
C8—C7—C12119.1 (4)C28—C27—C26117.9 (4)
C8—C7—C6133.2 (4)C28—C27—H27121.0
C12—C7—C6107.7 (3)C26—C27—H27121.0
C9—C8—C7117.6 (4)C27—C28—C29122.2 (4)
C9—C8—H8121.2C27—C28—Br5119.0 (3)
C7—C8—H8121.2C29—C28—Br5118.8 (3)
C8—C9—C10123.4 (4)C30—C29—C28121.0 (4)
C8—C9—Br2118.2 (3)C30—C29—H29119.5
C10—C9—Br2118.4 (3)C28—C29—H29119.5
C11—C10—C9119.7 (4)C29—C30—C31117.8 (4)
C11—C10—H10120.1C29—C30—H30121.1
C9—C10—H10120.1C31—C30—H30121.1
C10—C11—C12117.7 (4)N2—C31—C30129.6 (4)
C10—C11—H11121.2N2—C31—C26109.1 (4)
C12—C11—H11121.2C30—C31—C26121.2 (4)
N1—C12—C11129.1 (4)N2—C32—C33113.5 (3)
N1—C12—C7108.5 (4)N2—C32—H32A108.9
C11—C12—C7122.4 (4)C33—C32—H32A108.9
N1—C13—C14114.7 (3)N2—C32—H32B108.9
N1—C13—H13A108.6C33—C32—H32B108.9
C14—C13—H13A108.6H32A—C32—H32B107.7
N1—C13—H13B108.6C38—C33—C34118.6 (4)
C14—C13—H13B108.6C38—C33—C32121.2 (4)
H13A—C13—H13B107.6C34—C33—C32120.2 (4)
C19—C14—C15118.3 (4)C35—C34—C33120.6 (4)
C19—C14—C13120.4 (4)C35—C34—H34119.7
C15—C14—C13121.2 (4)C33—C34—H34119.7
C16—C15—C14120.8 (4)C34—C35—C36119.5 (4)
C16—C15—H15119.6C34—C35—H35120.2
C14—C15—H15119.6C36—C35—H35120.2
C17—C16—C15119.0 (4)C37—C36—C35121.2 (4)
C17—C16—H16120.5C37—C36—Br6118.7 (3)
C15—C16—H16120.5C35—C36—Br6120.1 (3)
C18—C17—C16121.5 (4)C36—C37—C38118.7 (4)
C18—C17—Br3119.8 (3)C36—C37—H37120.7
C16—C17—Br3118.7 (3)C38—C37—H37120.7
C17—C18—C19119.2 (4)C37—C38—C33121.3 (4)
C17—C18—H18120.4C37—C38—H38119.3
C19—C18—H18120.4C33—C38—H38119.3
C12—N1—C1—C2−177.0 (4)C31—N2—C20—C21−179.7 (4)
C13—N1—C1—C2−5.2 (7)C32—N2—C20—C21−0.8 (7)
C12—N1—C1—C62.9 (4)C31—N2—C20—C251.6 (4)
C13—N1—C1—C6174.7 (3)C32—N2—C20—C25−179.5 (3)
N1—C1—C2—C3178.9 (4)N2—C20—C21—C22179.2 (4)
C6—C1—C2—C3−1.0 (6)C25—C20—C21—C22−2.2 (6)
C1—C2—C3—C40.8 (6)C20—C21—C22—C230.8 (6)
C2—C3—C4—C50.3 (6)C21—C22—C23—C241.2 (6)
C2—C3—C4—Br1−177.9 (3)C21—C22—C23—Br4−176.4 (3)
C3—C4—C5—C6−1.1 (6)C22—C23—C24—C25−1.6 (6)
Br1—C4—C5—C6177.1 (3)Br4—C23—C24—C25175.9 (3)
C4—C5—C6—C10.8 (6)C23—C24—C25—C200.1 (6)
C4—C5—C6—C7−175.9 (4)C23—C24—C25—C26−177.4 (4)
C2—C1—C6—C50.2 (6)N2—C20—C25—C24−179.4 (3)
N1—C1—C6—C5−179.7 (3)C21—C20—C25—C241.7 (6)
C2—C1—C6—C7177.8 (4)N2—C20—C25—C26−1.2 (4)
N1—C1—C6—C7−2.1 (4)C21—C20—C25—C26179.9 (3)
C5—C6—C7—C80.3 (8)C24—C25—C26—C270.1 (8)
C1—C6—C7—C8−176.8 (4)C20—C25—C26—C27−177.7 (4)
C5—C6—C7—C12177.7 (4)C24—C25—C26—C31178.2 (4)
C1—C6—C7—C120.6 (4)C20—C25—C26—C310.5 (4)
C12—C7—C8—C90.0 (6)C31—C26—C27—C28−1.3 (6)
C6—C7—C8—C9177.1 (4)C25—C26—C27—C28176.7 (4)
C7—C8—C9—C10−0.3 (6)C26—C27—C28—C291.0 (6)
C7—C8—C9—Br2−179.0 (3)C26—C27—C28—Br5−178.0 (3)
C8—C9—C10—C110.4 (6)C27—C28—C29—C30−0.1 (6)
Br2—C9—C10—C11179.1 (3)Br5—C28—C29—C30179.0 (3)
C9—C10—C11—C12−0.2 (6)C28—C29—C30—C31−0.7 (6)
C1—N1—C12—C11176.2 (4)C20—N2—C31—C30176.9 (4)
C13—N1—C12—C114.4 (6)C32—N2—C31—C30−2.0 (6)
C1—N1—C12—C7−2.5 (4)C20—N2—C31—C26−1.3 (4)
C13—N1—C12—C7−174.3 (3)C32—N2—C31—C26179.8 (3)
C10—C11—C12—N1−178.6 (4)C29—C30—C31—N2−177.6 (4)
C10—C11—C12—C7−0.1 (6)C29—C30—C31—C260.4 (6)
C8—C7—C12—N1178.9 (3)C27—C26—C31—N2178.9 (4)
C6—C7—C12—N11.1 (4)C25—C26—C31—N20.5 (4)
C8—C7—C12—C110.2 (6)C27—C26—C31—C300.6 (6)
C6—C7—C12—C11−177.6 (4)C25—C26—C31—C30−177.9 (4)
C1—N1—C13—C1492.1 (5)C31—N2—C32—C33−88.0 (5)
C12—N1—C13—C14−97.4 (5)C20—N2—C32—C3393.2 (5)
N1—C13—C14—C19−101.7 (4)N2—C32—C33—C38−49.9 (5)
N1—C13—C14—C1581.2 (5)N2—C32—C33—C34133.0 (4)
C19—C14—C15—C16−0.5 (6)C38—C33—C34—C35−0.5 (6)
C13—C14—C15—C16176.7 (3)C32—C33—C34—C35176.7 (4)
C14—C15—C16—C17−0.7 (6)C33—C34—C35—C36−0.3 (6)
C15—C16—C17—C181.1 (6)C34—C35—C36—C371.7 (6)
C15—C16—C17—Br3−178.7 (3)C34—C35—C36—Br6−176.8 (3)
C16—C17—C18—C19−0.4 (6)C35—C36—C37—C38−2.1 (6)
Br3—C17—C18—C19179.5 (3)Br6—C36—C37—C38176.4 (3)
C17—C18—C19—C14−0.9 (6)C36—C37—C38—C331.3 (6)
C15—C14—C19—C181.3 (6)C34—C33—C38—C37−0.1 (6)
C13—C14—C19—C18−175.9 (3)C32—C33—C38—C37−177.2 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2546).

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