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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Jul 23;64(Pt 8):o1567. doi: 10.1107/S1600536808022174

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

Duan-Lin Cao a,b,*, Jian-Lan Cui b, Wei Mao b
PMCID: PMC2962237  PMID: 21203270

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 ▶); Caulfield et al. (2002 ▶); Harfenist & Joyner (1983 ▶); Harper et al. (2002 ▶). For the preparation of the title compound, see: Duan et al. (2005 ▶); Smith et al. (1992 ▶). For reference structural data, see: Allen et al. (1987 ▶).graphic file with name e-64-o1567-scheme1.jpg

Experimental

Crystal data

  • C23H21Br2N

  • M r = 471.23

  • Triclinic, Inline graphic

  • 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 ▶) 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 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

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

e-64-o1567-sup1.cif (30.9KB, cif)

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

e-64-o1567-Isup2.hkl (337.2KB, 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.

Fig. 1.

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

Crystal data

C23H21Br2N Z = 4
Mr = 471.23 F000 = 944
Triclinic, P1 Dx = 1.598 Mg m−3
Hall symbol: -P 1 Melting point = 434–435 K
a = 11.240 (2) Å Mo Kα radiation λ = 0.71073 Å
b = 12.921 (3) Å Cell parameters from 3716 reflections
c = 15.694 (3) Å θ = 1.5–27.9º
α = 105.43 (3)º µ = 4.15 mm−1
β = 108.53 (3)º T = 113 (2) K
γ = 103.09 (3)º Prism, colorless
V = 1958.9 (10) Å3 0.10 × 0.08 × 0.04 mm
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Data collection

Rigaku Saturn CCD diffractometer 6891 independent reflections
Radiation source: rotating anode 4712 reflections with I > 2σ(I)
Monochromator: confocal Rint = 0.051
T = 293(2) K θmax = 25.0º
ω scans θmin = 1.5º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005) h = −9→13
Tmin = 0.682, Tmax = 0.852 k = −15→15
12085 measured reflections l = −18→17
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Refinement

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)] = 0.055 H-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 reflections Δρmax = 0.46 e Å−3
475 parameters Δρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Br1 0.96240 (7) 0.27334 (4) 1.22201 (4) 0.03941 (19)
Br2 1.17197 (7) 0.38918 (5) 0.76081 (4) 0.04177 (19)
Br3 0.40645 (7) −0.22495 (4) 0.71466 (4) 0.04018 (19)
Br4 0.72986 (7) −0.12045 (5) 0.29922 (4) 0.03927 (18)
N1 0.7041 (5) 0.3752 (3) 0.8695 (3) 0.0221 (10)
N2 0.2243 (5) −0.1201 (3) 0.3530 (3) 0.0215 (10)
C1 0.7459 (6) 0.3489 (4) 0.9523 (3) 0.0250 (13)
C2 0.6817 (6) 0.3308 (4) 1.0116 (4) 0.0297 (14)
H2 0.5964 0.3345 0.9986 0.036*
C3 0.7475 (6) 0.3070 (4) 1.0907 (4) 0.0288 (14)
H3 0.7063 0.2949 1.1318 0.035*
C4 0.8725 (7) 0.3011 (4) 1.1094 (3) 0.0304 (15)
C5 0.9398 (6) 0.3174 (3) 1.0509 (3) 0.0237 (12)
H5 1.0248 0.3127 1.0645 0.028*
C6 0.8735 (6) 0.3410 (3) 0.9708 (3) 0.0216 (13)
C7 0.9125 (6) 0.3640 (4) 0.8957 (3) 0.0217 (12)
C8 1.0244 (6) 0.3672 (3) 0.8753 (3) 0.0240 (13)
H8 1.0964 0.3540 0.9146 0.029*
C9 1.0251 (6) 0.3906 (4) 0.7951 (4) 0.0277 (14)
C10 0.9171 (6) 0.4106 (4) 0.7345 (4) 0.0292 (15)
H10 0.9208 0.4257 0.6805 0.035*
C11 0.8074 (6) 0.4081 (4) 0.7545 (3) 0.0254 (13)
H11 0.7360 0.4216 0.7150 0.031*
C12 0.8049 (6) 0.3847 (3) 0.8359 (3) 0.0229 (13)
C13 0.5880 (6) 0.4076 (4) 0.8353 (4) 0.0336 (15)
H13A 0.5196 0.3697 0.8527 0.040*
H13B 0.5529 0.3822 0.7654 0.040*
C14 0.6203 (6) 0.5352 (4) 0.8772 (3) 0.0232 (12)
C15 0.6477 (6) 0.6037 (4) 0.8271 (3) 0.0320 (15)
H15 0.6390 0.5698 0.7642 0.038*
C16 0.6884 (6) 0.7231 (4) 0.8683 (3) 0.0289 (14)
H16 0.7070 0.7672 0.8329 0.035*
C17 0.7008 (5) 0.7753 (4) 0.9615 (3) 0.0198 (12)
C18 0.6714 (6) 0.7060 (4) 1.0113 (4) 0.0250 (13)
H18 0.6781 0.7395 1.0737 0.030*
C19 0.6323 (6) 0.5881 (4) 0.9705 (4) 0.0283 (14)
H19 0.6141 0.5440 1.0060 0.034*
C20 0.7512 (6) 0.9073 (4) 1.0123 (3) 0.0233 (13)
C21 0.7776 (7) 0.9676 (4) 0.9457 (4) 0.0401 (17)
H21A 0.8144 1.0487 0.9806 0.060*
H21B 0.6954 0.9496 0.8920 0.060*
H21C 0.8396 0.9428 0.9225 0.060*
C22 0.6453 (7) 0.9413 (4) 1.0432 (4) 0.0412 (17)
H22A 0.6290 0.9043 1.0860 0.062*
H22B 0.5642 0.9184 0.9872 0.062*
H22C 0.6763 1.0226 1.0759 0.062*
C23 0.8795 (6) 0.9417 (4) 1.1000 (4) 0.0365 (16)
H23A 0.9436 0.9160 1.0801 0.055*
H23B 0.8620 0.9076 1.1441 0.055*
H23C 0.9144 1.0233 1.1313 0.055*
C24 0.2497 (6) −0.1459 (3) 0.4368 (3) 0.0232 (13)
C25 0.1684 (6) −0.1601 (4) 0.4870 (3) 0.0267 (13)
H25 0.0844 −0.1531 0.4661 0.032*
C26 0.2170 (7) −0.1848 (4) 0.5688 (4) 0.0312 (15)
H26 0.1651 −0.1951 0.6037 0.037*
C27 0.3413 (6) −0.1944 (4) 0.5992 (3) 0.0242 (13)
C28 0.4236 (6) −0.1816 (3) 0.5510 (3) 0.0225 (13)
H28 0.5070 −0.1895 0.5727 0.027*
C29 0.3755 (6) −0.1560 (4) 0.4675 (3) 0.0202 (12)
C30 0.4306 (6) −0.1369 (3) 0.3996 (3) 0.0209 (12)
C31 0.5495 (6) −0.1379 (4) 0.3913 (3) 0.0244 (13)
H31 0.6138 −0.1528 0.4361 0.029*
C32 0.5699 (6) −0.1164 (4) 0.3150 (4) 0.0253 (13)
C33 0.4756 (6) −0.0936 (4) 0.2466 (4) 0.0267 (13)
H33 0.4931 −0.0787 0.1961 0.032*
C34 0.3577 (6) −0.0931 (3) 0.2537 (3) 0.0257 (14)
H34 0.2938 −0.0791 0.2080 0.031*
C35 0.3351 (6) −0.1141 (3) 0.3311 (3) 0.0185 (12)
C36 0.1124 (6) −0.0882 (3) 0.3058 (3) 0.0249 (13)
H36A 0.0335 −0.1303 0.3111 0.030*
H36B 0.0947 −0.1087 0.2378 0.030*
C37 0.1396 (6) 0.0393 (4) 0.3505 (3) 0.0245 (13)
C38 0.2053 (6) 0.1155 (4) 0.3192 (3) 0.0256 (13)
H38 0.2276 0.0881 0.2674 0.031*
C39 0.2386 (6) 0.2327 (4) 0.3642 (3) 0.0268 (13)
H39 0.2827 0.2821 0.3418 0.032*
C40 0.2080 (5) 0.2775 (4) 0.4414 (3) 0.0188 (11)
C41 0.1410 (6) 0.1999 (4) 0.4720 (3) 0.0266 (13)
H41 0.1189 0.2270 0.5240 0.032*
C42 0.1066 (6) 0.0831 (4) 0.4264 (4) 0.0281 (13)
H42 0.0602 0.0334 0.4475 0.034*
C43 0.2505 (6) 0.4068 (4) 0.4975 (3) 0.0218 (12)
C44 0.1313 (6) 0.4382 (4) 0.5087 (4) 0.0309 (14)
H44A 0.0954 0.3954 0.5417 0.046*
H44B 0.0639 0.4204 0.4460 0.046*
H44C 0.1600 0.5183 0.5453 0.046*
C45 0.3586 (6) 0.4352 (4) 0.5971 (3) 0.0304 (14)
H45A 0.3235 0.3919 0.6300 0.046*
H45B 0.3866 0.5153 0.6339 0.046*
H45C 0.4335 0.4164 0.5897 0.046*
C46 0.3061 (6) 0.4770 (4) 0.4454 (4) 0.0323 (15)
H46A 0.3331 0.5569 0.4823 0.048*
H46B 0.2385 0.4589 0.3827 0.048*
H46C 0.3817 0.4592 0.4384 0.048*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Br1 0.0530 (5) 0.0296 (3) 0.0276 (3) 0.0098 (3) 0.0069 (3) 0.0133 (2)
Br2 0.0489 (5) 0.0399 (3) 0.0429 (3) 0.0163 (3) 0.0301 (4) 0.0095 (3)
Br3 0.0521 (5) 0.0372 (3) 0.0297 (3) 0.0113 (3) 0.0126 (3) 0.0177 (2)
Br4 0.0338 (5) 0.0463 (3) 0.0379 (3) 0.0149 (3) 0.0215 (3) 0.0062 (3)
N1 0.014 (3) 0.0200 (19) 0.025 (2) 0.007 (2) −0.001 (2) 0.0091 (17)
N2 0.023 (3) 0.0172 (19) 0.028 (2) 0.011 (2) 0.007 (2) 0.0121 (17)
C1 0.033 (4) 0.012 (2) 0.030 (3) 0.010 (3) 0.012 (3) 0.005 (2)
C2 0.031 (4) 0.018 (2) 0.037 (3) 0.007 (3) 0.013 (3) 0.009 (2)
C3 0.030 (4) 0.024 (2) 0.032 (3) 0.007 (3) 0.015 (3) 0.008 (2)
C4 0.044 (5) 0.016 (2) 0.024 (3) 0.005 (3) 0.010 (3) 0.005 (2)
C5 0.021 (4) 0.015 (2) 0.028 (3) 0.007 (2) 0.004 (3) 0.004 (2)
C6 0.025 (4) 0.010 (2) 0.021 (2) 0.005 (2) 0.004 (3) 0.0003 (19)
C7 0.024 (4) 0.013 (2) 0.021 (2) 0.006 (2) 0.003 (3) 0.0018 (19)
C8 0.026 (4) 0.015 (2) 0.023 (3) 0.006 (2) 0.005 (3) 0.001 (2)
C9 0.036 (4) 0.015 (2) 0.030 (3) 0.006 (3) 0.018 (3) 0.003 (2)
C10 0.045 (5) 0.016 (2) 0.026 (3) 0.005 (3) 0.018 (3) 0.007 (2)
C11 0.023 (4) 0.019 (2) 0.022 (3) 0.001 (2) −0.001 (3) 0.007 (2)
C12 0.029 (4) 0.012 (2) 0.026 (3) 0.005 (2) 0.013 (3) 0.002 (2)
C13 0.030 (4) 0.025 (3) 0.034 (3) 0.007 (3) 0.002 (3) 0.009 (2)
C14 0.012 (4) 0.022 (2) 0.026 (3) 0.005 (2) −0.001 (3) 0.005 (2)
C15 0.046 (5) 0.026 (3) 0.023 (3) 0.022 (3) 0.009 (3) 0.008 (2)
C16 0.035 (4) 0.028 (3) 0.022 (3) 0.012 (3) 0.003 (3) 0.015 (2)
C17 0.012 (3) 0.020 (2) 0.023 (2) 0.005 (2) 0.003 (3) 0.007 (2)
C18 0.025 (4) 0.027 (3) 0.027 (3) 0.011 (3) 0.015 (3) 0.009 (2)
C19 0.032 (4) 0.024 (2) 0.038 (3) 0.013 (3) 0.020 (3) 0.016 (2)
C20 0.023 (4) 0.018 (2) 0.021 (2) 0.004 (2) 0.003 (3) 0.003 (2)
C21 0.063 (6) 0.019 (2) 0.034 (3) 0.009 (3) 0.019 (4) 0.009 (2)
C22 0.048 (5) 0.031 (3) 0.049 (4) 0.017 (3) 0.024 (4) 0.012 (3)
C23 0.036 (5) 0.024 (3) 0.034 (3) −0.001 (3) 0.007 (3) 0.004 (2)
C24 0.026 (4) 0.012 (2) 0.019 (2) 0.000 (2) 0.001 (3) 0.0006 (19)
C25 0.022 (4) 0.022 (2) 0.028 (3) 0.005 (2) 0.006 (3) 0.005 (2)
C26 0.039 (5) 0.025 (3) 0.032 (3) 0.008 (3) 0.020 (3) 0.010 (2)
C27 0.023 (4) 0.017 (2) 0.028 (3) 0.002 (2) 0.007 (3) 0.008 (2)
C28 0.022 (4) 0.015 (2) 0.023 (2) 0.005 (2) 0.004 (3) 0.003 (2)
C29 0.019 (4) 0.015 (2) 0.019 (2) 0.004 (2) 0.004 (3) 0.0010 (19)
C30 0.026 (4) 0.012 (2) 0.024 (3) 0.006 (2) 0.012 (3) 0.0015 (19)
C31 0.028 (4) 0.019 (2) 0.021 (2) 0.007 (2) 0.006 (3) 0.004 (2)
C32 0.025 (4) 0.014 (2) 0.030 (3) 0.003 (2) 0.013 (3) −0.002 (2)
C33 0.028 (4) 0.020 (2) 0.030 (3) 0.002 (3) 0.014 (3) 0.006 (2)
C34 0.034 (4) 0.016 (2) 0.022 (3) 0.004 (3) 0.010 (3) 0.007 (2)
C35 0.020 (4) 0.011 (2) 0.020 (2) 0.007 (2) 0.006 (3) 0.0008 (19)
C36 0.027 (4) 0.016 (2) 0.026 (3) 0.007 (2) 0.009 (3) 0.002 (2)
C37 0.024 (4) 0.026 (2) 0.023 (3) 0.012 (3) 0.006 (3) 0.009 (2)
C38 0.032 (4) 0.031 (3) 0.021 (2) 0.017 (3) 0.014 (3) 0.012 (2)
C39 0.036 (4) 0.024 (2) 0.030 (3) 0.014 (3) 0.016 (3) 0.017 (2)
C40 0.009 (3) 0.023 (2) 0.014 (2) 0.006 (2) −0.005 (2) 0.0032 (19)
C41 0.027 (4) 0.029 (3) 0.026 (3) 0.010 (3) 0.012 (3) 0.011 (2)
C42 0.024 (4) 0.022 (2) 0.041 (3) 0.005 (3) 0.016 (3) 0.013 (2)
C43 0.019 (4) 0.021 (2) 0.023 (2) 0.005 (2) 0.009 (3) 0.005 (2)
C44 0.036 (5) 0.026 (3) 0.031 (3) 0.013 (3) 0.015 (3) 0.007 (2)
C45 0.032 (4) 0.027 (3) 0.027 (3) 0.008 (3) 0.008 (3) 0.009 (2)
C46 0.042 (5) 0.022 (2) 0.033 (3) 0.013 (3) 0.015 (3) 0.010 (2)
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Geometric parameters (Å, °)

Br1—C4 1.908 (5) C22—H22B 0.9600
Br2—C9 1.894 (6) C22—H22C 0.9600
Br3—C27 1.909 (5) C23—H23A 0.9600
Br4—C32 1.901 (6) C23—H23B 0.9600
N1—C12 1.388 (7) C23—H23C 0.9600
N1—C1 1.395 (6) C24—C29 1.391 (8)
N1—C13 1.445 (7) C24—C25 1.397 (7)
N2—C35 1.384 (6) C25—C26 1.379 (7)
N2—C24 1.399 (6) C25—H25 0.9300
N2—C36 1.452 (7) C26—C27 1.372 (8)
C1—C2 1.381 (7) C26—H26 0.9300
C1—C6 1.403 (8) C27—C28 1.377 (7)
C2—C3 1.380 (7) C28—C29 1.408 (6)
C2—H2 0.9300 C28—H28 0.9300
C3—C4 1.366 (8) C29—C30 1.438 (6)
C3—H3 0.9300 C30—C31 1.386 (7)
C4—C5 1.390 (7) C30—C35 1.406 (7)
C5—C6 1.393 (7) C31—C32 1.374 (6)
C5—H5 0.9300 C31—H31 0.9300
C6—C7 1.457 (6) C32—C33 1.396 (8)
C7—C8 1.388 (7) C33—C34 1.367 (8)
C7—C12 1.405 (8) C33—H33 0.9300
C8—C9 1.372 (6) C34—C35 1.398 (6)
C8—H8 0.9300 C34—H34 0.9300
C9—C10 1.409 (8) C36—C37 1.522 (6)
C10—C11 1.362 (8) C36—H36A 0.9700
C10—H10 0.9300 C36—H36B 0.9700
C11—C12 1.396 (6) C37—C42 1.377 (6)
C11—H11 0.9300 C37—C38 1.384 (6)
C13—C14 1.512 (6) C38—C39 1.392 (6)
C13—H13A 0.9700 C38—H38 0.9300
C13—H13B 0.9700 C39—C40 1.379 (6)
C14—C15 1.376 (6) C39—H39 0.9300
C14—C19 1.389 (6) C40—C41 1.396 (6)
C15—C16 1.403 (6) C40—C43 1.544 (6)
C15—H15 0.9300 C41—C42 1.387 (6)
C16—C17 1.385 (6) C41—H41 0.9300
C16—H16 0.9300 C42—H42 0.9300
C17—C18 1.386 (6) C43—C45 1.529 (7)
C17—C20 1.554 (6) C43—C44 1.531 (7)
C18—C19 1.387 (6) C43—C46 1.531 (6)
C18—H18 0.9300 C44—H44A 0.9600
C19—H19 0.9300 C44—H44B 0.9600
C20—C23 1.515 (8) C44—H44C 0.9600
C20—C21 1.521 (6) C45—H45A 0.9600
C20—C22 1.529 (8) C45—H45B 0.9600
C21—H21A 0.9600 C45—H45C 0.9600
C21—H21B 0.9600 C46—H46A 0.9600
C21—H21C 0.9600 C46—H46B 0.9600
C22—H22A 0.9600 C46—H46C 0.9600
C12—N1—C1 108.1 (5) C20—C23—H23C 109.5
C12—N1—C13 125.4 (4) H23A—C23—H23C 109.5
C1—N1—C13 125.6 (5) H23B—C23—H23C 109.5
C35—N2—C24 107.4 (5) C29—C24—C25 121.7 (5)
C35—N2—C36 125.4 (4) C29—C24—N2 109.5 (4)
C24—N2—C36 126.5 (4) C25—C24—N2 128.8 (6)
C2—C1—N1 130.2 (6) C26—C25—C24 117.6 (6)
C2—C1—C6 121.0 (5) C26—C25—H25 121.2
N1—C1—C6 108.8 (4) C24—C25—H25 121.2
C3—C2—C1 118.2 (6) C27—C26—C25 120.6 (5)
C3—C2—H2 120.9 C27—C26—H26 119.7
C1—C2—H2 120.9 C25—C26—H26 119.7
C4—C3—C2 120.7 (5) C26—C27—C28 123.2 (5)
C4—C3—H3 119.6 C26—C27—Br3 119.2 (4)
C2—C3—H3 119.6 C28—C27—Br3 117.6 (4)
C3—C4—C5 122.8 (5) C27—C28—C29 116.9 (5)
C3—C4—Br1 119.4 (4) C27—C28—H28 121.5
C5—C4—Br1 117.8 (5) C29—C28—H28 121.5
C4—C5—C6 116.6 (6) C24—C29—C28 119.9 (5)
C4—C5—H5 121.7 C24—C29—C30 107.0 (4)
C6—C5—H5 121.7 C28—C29—C30 133.0 (5)
C5—C6—C1 120.7 (5) C31—C30—C35 119.9 (4)
C5—C6—C7 131.9 (5) C31—C30—C29 133.6 (5)
C1—C6—C7 107.4 (4) C35—C30—C29 106.5 (5)
C8—C7—C12 120.5 (4) C32—C31—C30 118.2 (5)
C8—C7—C6 134.0 (5) C32—C31—H31 120.9
C12—C7—C6 105.5 (5) C30—C31—H31 120.9
C9—C8—C7 117.6 (5) C31—C32—C33 122.3 (5)
C9—C8—H8 121.2 C31—C32—Br4 119.5 (4)
C7—C8—H8 121.2 C33—C32—Br4 118.2 (4)
C8—C9—C10 122.1 (5) C34—C33—C32 120.0 (5)
C8—C9—Br2 119.3 (5) C34—C33—H33 120.0
C10—C9—Br2 118.5 (4) C32—C33—H33 120.0
C11—C10—C9 120.4 (5) C33—C34—C35 118.7 (5)
C11—C10—H10 119.8 C33—C34—H34 120.7
C9—C10—H10 119.8 C35—C34—H34 120.7
C10—C11—C12 118.3 (5) N2—C35—C34 129.6 (5)
C10—C11—H11 120.8 N2—C35—C30 109.5 (4)
C12—C11—H11 120.8 C34—C35—C30 120.9 (5)
N1—C12—C11 128.8 (5) N2—C36—C37 111.7 (4)
N1—C12—C7 110.2 (4) N2—C36—H36A 109.3
C11—C12—C7 121.0 (5) C37—C36—H36A 109.3
N1—C13—C14 111.9 (5) N2—C36—H36B 109.3
N1—C13—H13A 109.2 C37—C36—H36B 109.3
C14—C13—H13A 109.2 H36A—C36—H36B 107.9
N1—C13—H13B 109.2 C42—C37—C38 117.8 (4)
C14—C13—H13B 109.2 C42—C37—C36 121.4 (4)
H13A—C13—H13B 107.9 C38—C37—C36 120.7 (4)
C15—C14—C19 117.8 (4) C37—C38—C39 120.9 (4)
C15—C14—C13 121.3 (4) C37—C38—H38 119.6
C19—C14—C13 120.7 (4) C39—C38—H38 119.6
C14—C15—C16 121.9 (4) C40—C39—C38 121.7 (4)
C14—C15—H15 119.1 C40—C39—H39 119.1
C16—C15—H15 119.1 C38—C39—H39 119.1
C17—C16—C15 120.1 (4) C39—C40—C41 116.9 (4)
C17—C16—H16 120.0 C39—C40—C43 123.5 (4)
C15—C16—H16 120.0 C41—C40—C43 119.4 (4)
C16—C17—C18 117.9 (4) C42—C41—C40 121.3 (4)
C16—C17—C20 122.3 (4) C42—C41—H41 119.4
C18—C17—C20 119.8 (4) C40—C41—H41 119.4
C17—C18—C19 121.8 (4) C37—C42—C41 121.3 (4)
C17—C18—H18 119.1 C37—C42—H42 119.3
C19—C18—H18 119.1 C41—C42—H42 119.3
C18—C19—C14 120.6 (4) C45—C43—C44 109.8 (4)
C18—C19—H19 119.7 C45—C43—C46 109.4 (4)
C14—C19—H19 119.7 C44—C43—C46 108.2 (4)
C23—C20—C21 109.3 (5) C45—C43—C40 107.6 (4)
C23—C20—C22 110.1 (4) C44—C43—C40 110.5 (4)
C21—C20—C22 109.0 (4) C46—C43—C40 111.3 (4)
C23—C20—C17 108.0 (4) C43—C44—H44A 109.5
C21—C20—C17 111.7 (4) C43—C44—H44B 109.5
C22—C20—C17 108.8 (4) H44A—C44—H44B 109.5
C20—C21—H21A 109.5 C43—C44—H44C 109.5
C20—C21—H21B 109.5 H44A—C44—H44C 109.5
H21A—C21—H21B 109.5 H44B—C44—H44C 109.5
C20—C21—H21C 109.5 C43—C45—H45A 109.5
H21A—C21—H21C 109.5 C43—C45—H45B 109.5
H21B—C21—H21C 109.5 H45A—C45—H45B 109.5
C20—C22—H22A 109.5 C43—C45—H45C 109.5
C20—C22—H22B 109.5 H45A—C45—H45C 109.5
H22A—C22—H22B 109.5 H45B—C45—H45C 109.5
C20—C22—H22C 109.5 C43—C46—H46A 109.5
H22A—C22—H22C 109.5 C43—C46—H46B 109.5
H22B—C22—H22C 109.5 H46A—C46—H46B 109.5
C20—C23—H23A 109.5 C43—C46—H46C 109.5
C20—C23—H23B 109.5 H46A—C46—H46C 109.5
H23A—C23—H23B 109.5 H46B—C46—H46C 109.5
C12—N1—C1—C2 −179.9 (4) C35—N2—C24—C29 0.0 (5)
C13—N1—C1—C2 10.5 (8) C36—N2—C24—C29 −171.3 (4)
C12—N1—C1—C6 −0.3 (5) C35—N2—C24—C25 179.6 (4)
C13—N1—C1—C6 −169.9 (4) C36—N2—C24—C25 8.3 (7)
N1—C1—C2—C3 −179.2 (5) C29—C24—C25—C26 −0.1 (7)
C6—C1—C2—C3 1.3 (7) N2—C24—C25—C26 −179.6 (4)
C1—C2—C3—C4 −0.3 (7) C24—C25—C26—C27 0.3 (7)
C2—C3—C4—C5 −0.5 (8) C25—C26—C27—C28 −0.7 (8)
C2—C3—C4—Br1 177.8 (3) C25—C26—C27—Br3 178.4 (3)
C3—C4—C5—C6 0.3 (7) C26—C27—C28—C29 0.8 (7)
Br1—C4—C5—C6 −178.1 (3) Br3—C27—C28—C29 −178.3 (3)
C4—C5—C6—C1 0.7 (6) C25—C24—C29—C28 0.2 (7)
C4—C5—C6—C7 179.1 (4) N2—C24—C29—C28 179.9 (4)
C2—C1—C6—C5 −1.5 (7) C25—C24—C29—C30 179.8 (4)
N1—C1—C6—C5 178.9 (4) N2—C24—C29—C30 −0.6 (5)
C2—C1—C6—C7 179.7 (4) C27—C28—C29—C24 −0.6 (6)
N1—C1—C6—C7 0.1 (5) C27—C28—C29—C30 −180.0 (4)
C5—C6—C7—C8 2.2 (8) C24—C29—C30—C31 −178.7 (5)
C1—C6—C7—C8 −179.2 (5) C28—C29—C30—C31 0.8 (9)
C5—C6—C7—C12 −178.5 (5) C24—C29—C30—C35 0.9 (5)
C1—C6—C7—C12 0.1 (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—C9 178.9 (4) C29—C30—C31—C32 179.5 (4)
C7—C8—C9—C10 −0.1 (7) C30—C31—C32—C33 0.1 (7)
C7—C8—C9—Br2 −177.2 (3) C30—C31—C32—Br4 −178.5 (3)
C8—C9—C10—C11 0.5 (7) C31—C32—C33—C34 −0.5 (7)
Br2—C9—C10—C11 177.5 (3) Br4—C32—C33—C34 178.1 (3)
C9—C10—C11—C12 −0.3 (7) C32—C33—C34—C35 0.9 (7)
C1—N1—C12—C11 178.9 (4) C24—N2—C35—C34 178.6 (4)
C13—N1—C12—C11 −11.5 (7) C36—N2—C35—C34 −9.9 (7)
C1—N1—C12—C7 0.4 (5) C24—N2—C35—C30 0.6 (5)
C13—N1—C12—C7 170.0 (4) C36—N2—C35—C30 172.0 (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—N1 179.1 (4) C31—C30—C35—N2 178.7 (4)
C6—C7—C12—N1 −0.3 (5) C29—C30—C35—N2 −0.9 (5)
C8—C7—C12—C11 0.5 (7) C31—C30—C35—C34 0.5 (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—C14 89.4 (6) C24—N2—C36—C37 85.0 (6)
N1—C13—C14—C15 96.5 (6) N2—C36—C37—C42 −90.0 (6)
N1—C13—C14—C19 −78.9 (7) N2—C36—C37—C38 86.4 (6)
C19—C14—C15—C16 0.8 (9) C42—C37—C38—C39 1.0 (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—C40 0.0 (9)
C15—C16—C17—C18 −0.2 (9) C38—C39—C40—C41 −0.4 (8)
C15—C16—C17—C20 177.3 (5) C38—C39—C40—C43 176.1 (5)
C16—C17—C18—C19 0.8 (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—C41 174.8 (5)
C13—C14—C19—C18 175.3 (5) C40—C41—C42—C37 1.4 (9)
C16—C17—C20—C23 −117.6 (6) C39—C40—C43—C45 −109.0 (6)
C18—C17—C20—C23 59.8 (6) C41—C40—C43—C45 67.4 (6)
C16—C17—C20—C21 2.6 (8) C39—C40—C43—C44 131.1 (5)
C18—C17—C20—C21 −180.0 (5) C41—C40—C43—C44 −52.5 (6)
C16—C17—C20—C22 122.9 (6) C39—C40—C43—C46 10.8 (7)
C18—C17—C20—C22 −59.7 (6) C41—C40—C43—C46 −172.8 (5)
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Footnotes

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

References

  1. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  2. Buu-Hoï, N. P. & Royer, R. (1950). J. Org. Chem.15, 123–130.
  3. Caulfield, T., Cherrier, M. P., Combeau, C. & Mailliet, P. (2002). European Patent 1253141.
  4. Duan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005). Fine Chem.22, 39–40, 52.
  5. Harfenist, M. & Joyner, C. T. (1983). US Patent No. 4 379 160.
  6. Harper, R. W., Lin, H. S. & Richett, M. E. (2002). World Patent No. 02079154.
  7. Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  8. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  9. Smith, K., James, D. M., Mistry, A. G., Bye, M. R. & Faulkner, D. J. (1992). Tetrahedron, 48, 7479–7488.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-64-o1567-sup1.cif (30.9KB, cif)

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

e-64-o1567-Isup2.hkl (337.2KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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