Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Jan 8;65(Pt 2):o216. doi: 10.1107/S1600536808042827

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

Jian-lan Cui a,*, Mei Duan b, Liu-qing Cai a
PMCID: PMC2968375  PMID: 21581835

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 ▶); Caulfield et al. (2002 ▶); Harfenist & Joyner (1983 ▶); Harper et al. (2002 ▶). For bond length data, see: Allen et al. (1987 ▶). For the synthesis of the title compound, see: Duan et al. (2005a ▶,b ▶); Smith et al. (1992 ▶). For related literature, see: Borzatta & Carrozza (1991 ▶). For a related structure, see: Cui et al. (2009 ▶).graphic file with name e-65-0o216-scheme1.jpg

Experimental

Crystal data

  • C19H12Br3N

  • M r = 494.00

  • Monoclinic, Inline graphic

  • 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 ▶) 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 ▶); 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/S1600536808042827/sj2546sup1.cif

e-65-0o216-sup1.cif (26.8KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042827/sj2546Isup2.hkl

e-65-0o216-Isup2.hkl (382.8KB, 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.

Fig. 1.

Open in a new tab

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

Crystal data

C19H12Br3N F(000) = 1904
Mr = 494.00 Dx = 1.996 Mg m−3
Monoclinic, P21/n Melting point = 480–481 K
Hall symbol: -P 2yn Mo Kα radiation, λ = 0.71073 Å
a = 9.4784 (19) Å Cell parameters from 6869 reflections
b = 17.132 (3) Å θ = 1.6–28.0°
c = 20.456 (4) Å µ = 7.36 mm−1
β = 98.16 (3)° T = 113 K
V = 3288.1 (11) Å3 Prism, colorless
Z = 8 0.08 × 0.02 × 0.02 mm
Open in a new tab

Data collection

Rigaku Saturn diffractometer 7824 independent reflections
Radiation source: rotating anode 6058 reflections with I > 2σ(I)
confocal Rint = 0.054
ω scans θmax = 27.9°, θmin = 1.6°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) h = −12→10
Tmin = 0.591, Tmax = 0.867 k = −20→22
25134 measured reflections l = −26→26
Open in a new tab

Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103 H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
7824 reflections (Δ/σ)max = 0.002
415 parameters Δρmax = 0.62 e Å−3
0 restraints Δρmin = −0.86 e Å−3
Open in a new tab

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.
Open in a new tab

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

x y z Uiso*/Ueq
Br1 −0.14151 (4) 0.08974 (2) 0.20844 (2) 0.02780 (12)
Br2 0.26336 (5) 0.39468 (3) 0.51841 (2) 0.03025 (12)
Br3 0.10307 (5) 0.67522 (3) 0.01113 (2) 0.02914 (12)
Br4 0.36237 (4) 0.08294 (2) 0.17850 (2) 0.02334 (11)
Br5 0.71818 (6) 0.37880 (3) 0.50564 (2) 0.03361 (13)
Br6 0.57775 (5) 0.68767 (2) 0.03165 (2) 0.02995 (12)
N1 0.2671 (3) 0.36064 (19) 0.22607 (17) 0.0202 (7)
N2 0.7685 (3) 0.35444 (19) 0.21649 (16) 0.0191 (7)
C1 0.1733 (4) 0.2987 (2) 0.2121 (2) 0.0185 (8)
C2 0.1328 (4) 0.2593 (2) 0.1533 (2) 0.0209 (9)
H2 0.1683 0.2737 0.1150 0.025*
C3 0.0377 (4) 0.1977 (2) 0.1532 (2) 0.0226 (9)
H3 0.0097 0.1698 0.1145 0.027*
C4 −0.0161 (4) 0.1774 (2) 0.2112 (2) 0.0228 (9)
C5 0.0207 (4) 0.2165 (2) 0.2699 (2) 0.0218 (9)
H5 −0.0178 0.2025 0.3076 0.026*
C6 0.1174 (4) 0.2777 (2) 0.2708 (2) 0.0198 (9)
C7 0.1859 (4) 0.3280 (2) 0.3219 (2) 0.0192 (8)
C8 0.1804 (4) 0.3334 (2) 0.3900 (2) 0.0204 (9)
H8 0.1203 0.3014 0.4104 0.024*
C9 0.2673 (5) 0.3878 (2) 0.4256 (2) 0.0229 (9)
C10 0.3593 (4) 0.4368 (2) 0.3975 (2) 0.0214 (9)
H10 0.4161 0.4723 0.4237 0.026*
C11 0.3660 (4) 0.4324 (2) 0.3301 (2) 0.0204 (9)
H11 0.4266 0.4646 0.3103 0.025*
C12 0.2786 (4) 0.3777 (2) 0.2932 (2) 0.0181 (8)
C13 0.3542 (4) 0.3943 (2) 0.1802 (2) 0.0197 (9)
H13A 0.3758 0.3538 0.1500 0.024*
H13B 0.4437 0.4115 0.2050 0.024*
C14 0.2862 (4) 0.4627 (2) 0.1401 (2) 0.0202 (9)
C15 0.2893 (4) 0.5380 (2) 0.1667 (2) 0.0223 (9)
H15 0.3293 0.5461 0.2103 0.027*
C16 0.2335 (4) 0.6010 (2) 0.1286 (2) 0.0228 (9)
H16 0.2349 0.6508 0.1466 0.027*
C17 0.1758 (4) 0.5882 (2) 0.0636 (2) 0.0205 (9)
C18 0.1704 (4) 0.5147 (2) 0.0362 (2) 0.0217 (9)
H18 0.1308 0.5071 −0.0076 0.026*
C19 0.2245 (4) 0.4523 (2) 0.0745 (2) 0.0204 (9)
H19 0.2198 0.4024 0.0564 0.024*
C20 0.6758 (4) 0.2931 (2) 0.1978 (2) 0.0175 (8)
C21 0.6408 (4) 0.2566 (2) 0.1368 (2) 0.0187 (8)
H21 0.6808 0.2732 0.1003 0.022*
C22 0.5455 (4) 0.1955 (2) 0.1317 (2) 0.0195 (8)
H22 0.5214 0.1699 0.0916 0.023*
C23 0.4851 (4) 0.1720 (2) 0.1870 (2) 0.0202 (9)
C24 0.5139 (4) 0.2079 (2) 0.2474 (2) 0.0195 (8)
H24 0.4704 0.1918 0.2831 0.023*
C25 0.6115 (4) 0.2698 (2) 0.25318 (19) 0.0169 (8)
C26 0.6708 (4) 0.3185 (2) 0.3077 (2) 0.0202 (9)
C27 0.6534 (5) 0.3220 (2) 0.3746 (2) 0.0224 (9)
H27 0.5888 0.2895 0.3917 0.027*
C28 0.7347 (4) 0.3749 (2) 0.4143 (2) 0.0225 (9)
C29 0.8310 (5) 0.4252 (2) 0.3896 (2) 0.0253 (10)
H29 0.8839 0.4601 0.4180 0.030*
C30 0.8487 (4) 0.4238 (2) 0.3237 (2) 0.0240 (9)
H30 0.9119 0.4575 0.3072 0.029*
C31 0.7682 (4) 0.3698 (2) 0.2827 (2) 0.0192 (8)
C32 0.8553 (4) 0.3959 (2) 0.1744 (2) 0.0214 (9)
H32A 0.8769 0.3609 0.1399 0.026*
H32B 0.9448 0.4106 0.2006 0.026*
C33 0.7844 (4) 0.4684 (2) 0.14287 (19) 0.0191 (8)
C34 0.8599 (5) 0.5385 (2) 0.1439 (2) 0.0239 (9)
H34 0.9524 0.5411 0.1661 0.029*
C35 0.7984 (5) 0.6039 (2) 0.1124 (2) 0.0256 (10)
H35 0.8491 0.6505 0.1135 0.031*
C36 0.6604 (4) 0.5997 (2) 0.0790 (2) 0.0218 (9)
C37 0.5819 (4) 0.5316 (2) 0.0782 (2) 0.0219 (9)
H37 0.4884 0.5298 0.0570 0.026*
C38 0.6452 (4) 0.4661 (2) 0.1096 (2) 0.0217 (9)
H38 0.5939 0.4198 0.1085 0.026*
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Br1 0.0208 (2) 0.0208 (2) 0.0402 (3) −0.00171 (17) −0.00107 (19) 0.00121 (19)
Br2 0.0424 (3) 0.0291 (3) 0.0198 (2) 0.0031 (2) 0.0065 (2) 0.00106 (18)
Br3 0.0335 (2) 0.0247 (2) 0.0277 (2) 0.00291 (18) −0.0008 (2) 0.00693 (19)
Br4 0.0224 (2) 0.0197 (2) 0.0266 (2) −0.00224 (16) −0.00116 (18) 0.00099 (17)
Br5 0.0505 (3) 0.0309 (3) 0.0183 (2) 0.0093 (2) 0.0009 (2) −0.00347 (19)
Br6 0.0369 (3) 0.0202 (2) 0.0314 (3) 0.00635 (18) 0.0000 (2) 0.00390 (19)
N1 0.0176 (16) 0.0219 (18) 0.0208 (18) −0.0027 (14) 0.0016 (14) 0.0009 (15)
N2 0.0230 (17) 0.0165 (17) 0.0172 (17) −0.0009 (14) 0.0005 (15) −0.0007 (14)
C1 0.0189 (19) 0.0113 (19) 0.025 (2) 0.0029 (15) 0.0014 (17) 0.0007 (17)
C2 0.020 (2) 0.021 (2) 0.021 (2) 0.0048 (17) −0.0010 (17) 0.0020 (17)
C3 0.019 (2) 0.021 (2) 0.025 (2) 0.0010 (17) −0.0058 (18) −0.0044 (18)
C4 0.021 (2) 0.017 (2) 0.029 (2) 0.0033 (17) −0.0019 (18) 0.0031 (18)
C5 0.019 (2) 0.018 (2) 0.027 (2) 0.0041 (16) 0.0004 (18) 0.0041 (18)
C6 0.0169 (19) 0.021 (2) 0.022 (2) 0.0040 (16) 0.0018 (17) 0.0057 (17)
C7 0.0160 (19) 0.016 (2) 0.025 (2) 0.0037 (16) 0.0015 (17) 0.0015 (17)
C8 0.023 (2) 0.019 (2) 0.019 (2) 0.0013 (17) 0.0017 (17) 0.0035 (17)
C9 0.030 (2) 0.021 (2) 0.017 (2) 0.0076 (18) 0.0002 (18) 0.0029 (17)
C10 0.027 (2) 0.016 (2) 0.021 (2) 0.0080 (17) 0.0002 (18) −0.0014 (17)
C11 0.022 (2) 0.016 (2) 0.022 (2) 0.0065 (16) 0.0002 (18) 0.0024 (17)
C12 0.0196 (19) 0.017 (2) 0.017 (2) 0.0086 (16) −0.0009 (16) 0.0050 (16)
C13 0.0184 (19) 0.021 (2) 0.020 (2) 0.0002 (16) 0.0052 (17) −0.0009 (17)
C14 0.018 (2) 0.021 (2) 0.021 (2) −0.0001 (16) 0.0032 (17) 0.0038 (17)
C15 0.024 (2) 0.028 (2) 0.014 (2) −0.0019 (18) 0.0016 (17) −0.0034 (18)
C16 0.024 (2) 0.018 (2) 0.027 (2) −0.0012 (17) 0.0052 (19) −0.0030 (18)
C17 0.020 (2) 0.021 (2) 0.020 (2) −0.0014 (17) 0.0027 (17) 0.0016 (17)
C18 0.020 (2) 0.029 (2) 0.015 (2) −0.0055 (17) −0.0019 (17) −0.0013 (18)
C19 0.0183 (19) 0.020 (2) 0.023 (2) −0.0026 (16) 0.0048 (17) 0.0007 (17)
C20 0.0151 (18) 0.016 (2) 0.020 (2) 0.0031 (15) −0.0020 (16) −0.0016 (16)
C21 0.021 (2) 0.018 (2) 0.017 (2) 0.0033 (16) 0.0025 (17) 0.0012 (16)
C22 0.022 (2) 0.019 (2) 0.017 (2) 0.0020 (16) 0.0012 (17) −0.0016 (16)
C23 0.020 (2) 0.016 (2) 0.023 (2) 0.0023 (16) −0.0022 (17) 0.0046 (17)
C24 0.025 (2) 0.016 (2) 0.018 (2) 0.0015 (17) 0.0036 (17) 0.0014 (16)
C25 0.0188 (19) 0.016 (2) 0.0150 (19) 0.0045 (15) −0.0008 (16) 0.0033 (16)
C26 0.024 (2) 0.018 (2) 0.018 (2) 0.0071 (17) 0.0010 (17) 0.0048 (17)
C27 0.027 (2) 0.019 (2) 0.020 (2) 0.0053 (17) 0.0023 (18) 0.0021 (17)
C28 0.028 (2) 0.023 (2) 0.016 (2) 0.0100 (18) −0.0016 (18) 0.0012 (17)
C29 0.028 (2) 0.017 (2) 0.028 (2) 0.0042 (18) −0.005 (2) −0.0080 (18)
C30 0.024 (2) 0.019 (2) 0.028 (2) 0.0024 (17) 0.0005 (19) −0.0009 (18)
C31 0.0168 (19) 0.015 (2) 0.025 (2) 0.0070 (16) −0.0004 (17) 0.0025 (17)
C32 0.020 (2) 0.020 (2) 0.026 (2) 0.0001 (16) 0.0059 (18) 0.0031 (18)
C33 0.021 (2) 0.020 (2) 0.015 (2) 0.0045 (16) −0.0016 (16) 0.0012 (16)
C34 0.024 (2) 0.022 (2) 0.024 (2) −0.0034 (17) −0.0001 (18) −0.0021 (18)
C35 0.032 (2) 0.018 (2) 0.026 (2) −0.0057 (18) 0.001 (2) −0.0025 (18)
C36 0.023 (2) 0.021 (2) 0.022 (2) 0.0050 (17) 0.0049 (18) 0.0012 (17)
C37 0.020 (2) 0.025 (2) 0.021 (2) 0.0013 (17) 0.0038 (17) 0.0027 (18)
C38 0.021 (2) 0.021 (2) 0.024 (2) −0.0040 (17) 0.0058 (18) 0.0036 (18)
Open in a new tab

Geometric parameters (Å, °)

Br1—C4 1.911 (4) C16—C17 1.381 (6)
Br2—C9 1.908 (4) C16—H16 0.9300
Br3—C17 1.907 (4) C17—C18 1.377 (5)
Br4—C23 1.911 (4) C18—C19 1.381 (6)
Br5—C28 1.899 (4) C18—H18 0.9300
Br6—C36 1.900 (4) C19—H19 0.9300
N1—C1 1.387 (5) C20—C21 1.392 (5)
N1—C12 1.394 (5) C20—C25 1.418 (5)
N1—C13 1.454 (5) C21—C22 1.377 (5)
N2—C31 1.380 (5) C21—H21 0.9300
N2—C20 1.389 (5) C22—C23 1.397 (5)
N2—C32 1.457 (5) C22—H22 0.9300
C1—C2 1.385 (6) C23—C24 1.373 (6)
C1—C6 1.426 (5) C24—C25 1.401 (5)
C2—C3 1.387 (5) C24—H24 0.9300
C2—H2 0.9300 C25—C26 1.442 (6)
C3—C4 1.400 (6) C26—C27 1.403 (6)
C3—H3 0.9300 C26—C31 1.422 (5)
C4—C5 1.375 (6) C27—C28 1.377 (6)
C5—C6 1.392 (6) C27—H27 0.9300
C5—H5 0.9300 C28—C29 1.400 (6)
C6—C7 1.436 (6) C29—C30 1.382 (6)
C7—C8 1.404 (5) C29—H29 0.9300
C7—C12 1.410 (5) C30—C31 1.400 (6)
C8—C9 1.382 (6) C30—H30 0.9300
C8—H8 0.9300 C32—C33 1.512 (5)
C9—C10 1.392 (6) C32—H32A 0.9700
C10—C11 1.391 (6) C32—H32B 0.9700
C10—H10 0.9300 C33—C38 1.396 (6)
C11—C12 1.398 (6) C33—C34 1.396 (5)
C11—H11 0.9300 C34—C35 1.381 (6)
C13—C14 1.521 (5) C34—H34 0.9300
C13—H13A 0.9700 C35—C36 1.389 (6)
C13—H13B 0.9700 C35—H35 0.9300
C14—C19 1.397 (6) C36—C37 1.382 (5)
C14—C15 1.399 (6) C37—C38 1.387 (6)
C15—C16 1.390 (6) C37—H37 0.9300
C15—H15 0.9300 C38—H38 0.9300
C1—N1—C12 108.8 (3) C18—C19—C14 121.1 (4)
C1—N1—C13 125.2 (3) C18—C19—H19 119.4
C12—N1—C13 125.5 (3) C14—C19—H19 119.4
C31—N2—C20 109.0 (3) N2—C20—C21 130.3 (4)
C31—N2—C32 124.5 (3) N2—C20—C25 108.7 (3)
C20—N2—C32 126.5 (3) C21—C20—C25 121.0 (4)
C2—C1—N1 129.9 (4) C22—C21—C20 118.7 (4)
C2—C1—C6 121.2 (4) C22—C21—H21 120.7
N1—C1—C6 108.9 (4) C20—C21—H21 120.7
C1—C2—C3 118.2 (4) C21—C22—C23 119.8 (4)
C1—C2—H2 120.9 C21—C22—H22 120.1
C3—C2—H2 120.9 C23—C22—H22 120.1
C2—C3—C4 120.1 (4) C24—C23—C22 123.2 (4)
C2—C3—H3 119.9 C24—C23—Br4 118.7 (3)
C4—C3—H3 119.9 C22—C23—Br4 118.0 (3)
C5—C4—C3 122.8 (4) C23—C24—C25 117.3 (4)
C5—C4—Br1 119.2 (3) C23—C24—H24 121.3
C3—C4—Br1 118.0 (3) C25—C24—H24 121.3
C4—C5—C6 117.7 (4) C24—C25—C20 120.0 (4)
C4—C5—H5 121.2 C24—C25—C26 133.1 (4)
C6—C5—H5 121.2 C20—C25—C26 106.9 (3)
C5—C6—C1 120.1 (4) C27—C26—C31 119.9 (4)
C5—C6—C7 133.8 (4) C27—C26—C25 133.8 (4)
C1—C6—C7 106.1 (3) C31—C26—C25 106.3 (3)
C8—C7—C12 119.1 (4) C28—C27—C26 117.9 (4)
C8—C7—C6 133.2 (4) C28—C27—H27 121.0
C12—C7—C6 107.7 (3) C26—C27—H27 121.0
C9—C8—C7 117.6 (4) C27—C28—C29 122.2 (4)
C9—C8—H8 121.2 C27—C28—Br5 119.0 (3)
C7—C8—H8 121.2 C29—C28—Br5 118.8 (3)
C8—C9—C10 123.4 (4) C30—C29—C28 121.0 (4)
C8—C9—Br2 118.2 (3) C30—C29—H29 119.5
C10—C9—Br2 118.4 (3) C28—C29—H29 119.5
C11—C10—C9 119.7 (4) C29—C30—C31 117.8 (4)
C11—C10—H10 120.1 C29—C30—H30 121.1
C9—C10—H10 120.1 C31—C30—H30 121.1
C10—C11—C12 117.7 (4) N2—C31—C30 129.6 (4)
C10—C11—H11 121.2 N2—C31—C26 109.1 (4)
C12—C11—H11 121.2 C30—C31—C26 121.2 (4)
N1—C12—C11 129.1 (4) N2—C32—C33 113.5 (3)
N1—C12—C7 108.5 (4) N2—C32—H32A 108.9
C11—C12—C7 122.4 (4) C33—C32—H32A 108.9
N1—C13—C14 114.7 (3) N2—C32—H32B 108.9
N1—C13—H13A 108.6 C33—C32—H32B 108.9
C14—C13—H13A 108.6 H32A—C32—H32B 107.7
N1—C13—H13B 108.6 C38—C33—C34 118.6 (4)
C14—C13—H13B 108.6 C38—C33—C32 121.2 (4)
H13A—C13—H13B 107.6 C34—C33—C32 120.2 (4)
C19—C14—C15 118.3 (4) C35—C34—C33 120.6 (4)
C19—C14—C13 120.4 (4) C35—C34—H34 119.7
C15—C14—C13 121.2 (4) C33—C34—H34 119.7
C16—C15—C14 120.8 (4) C34—C35—C36 119.5 (4)
C16—C15—H15 119.6 C34—C35—H35 120.2
C14—C15—H15 119.6 C36—C35—H35 120.2
C17—C16—C15 119.0 (4) C37—C36—C35 121.2 (4)
C17—C16—H16 120.5 C37—C36—Br6 118.7 (3)
C15—C16—H16 120.5 C35—C36—Br6 120.1 (3)
C18—C17—C16 121.5 (4) C36—C37—C38 118.7 (4)
C18—C17—Br3 119.8 (3) C36—C37—H37 120.7
C16—C17—Br3 118.7 (3) C38—C37—H37 120.7
C17—C18—C19 119.2 (4) C37—C38—C33 121.3 (4)
C17—C18—H18 120.4 C37—C38—H38 119.3
C19—C18—H18 120.4 C33—C38—H38 119.3
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—C6 2.9 (4) C31—N2—C20—C25 1.6 (4)
C13—N1—C1—C6 174.7 (3) C32—N2—C20—C25 −179.5 (3)
N1—C1—C2—C3 178.9 (4) N2—C20—C21—C22 179.2 (4)
C6—C1—C2—C3 −1.0 (6) C25—C20—C21—C22 −2.2 (6)
C1—C2—C3—C4 0.8 (6) C20—C21—C22—C23 0.8 (6)
C2—C3—C4—C5 0.3 (6) C21—C22—C23—C24 1.2 (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—C6 177.1 (3) Br4—C23—C24—C25 175.9 (3)
C4—C5—C6—C1 0.8 (6) C23—C24—C25—C20 0.1 (6)
C4—C5—C6—C7 −175.9 (4) C23—C24—C25—C26 −177.4 (4)
C2—C1—C6—C5 0.2 (6) N2—C20—C25—C24 −179.4 (3)
N1—C1—C6—C5 −179.7 (3) C21—C20—C25—C24 1.7 (6)
C2—C1—C6—C7 177.8 (4) N2—C20—C25—C26 −1.2 (4)
N1—C1—C6—C7 −2.1 (4) C21—C20—C25—C26 179.9 (3)
C5—C6—C7—C8 0.3 (8) C24—C25—C26—C27 0.1 (8)
C1—C6—C7—C8 −176.8 (4) C20—C25—C26—C27 −177.7 (4)
C5—C6—C7—C12 177.7 (4) C24—C25—C26—C31 178.2 (4)
C1—C6—C7—C12 0.6 (4) C20—C25—C26—C31 0.5 (4)
C12—C7—C8—C9 0.0 (6) C31—C26—C27—C28 −1.3 (6)
C6—C7—C8—C9 177.1 (4) C25—C26—C27—C28 176.7 (4)
C7—C8—C9—C10 −0.3 (6) C26—C27—C28—C29 1.0 (6)
C7—C8—C9—Br2 −179.0 (3) C26—C27—C28—Br5 −178.0 (3)
C8—C9—C10—C11 0.4 (6) C27—C28—C29—C30 −0.1 (6)
Br2—C9—C10—C11 179.1 (3) Br5—C28—C29—C30 179.0 (3)
C9—C10—C11—C12 −0.2 (6) C28—C29—C30—C31 −0.7 (6)
C1—N1—C12—C11 176.2 (4) C20—N2—C31—C30 176.9 (4)
C13—N1—C12—C11 4.4 (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—C26 179.8 (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—C26 0.4 (6)
C8—C7—C12—N1 178.9 (3) C27—C26—C31—N2 178.9 (4)
C6—C7—C12—N1 1.1 (4) C25—C26—C31—N2 0.5 (4)
C8—C7—C12—C11 0.2 (6) C27—C26—C31—C30 0.6 (6)
C6—C7—C12—C11 −177.6 (4) C25—C26—C31—C30 −177.9 (4)
C1—N1—C13—C14 92.1 (5) C31—N2—C32—C33 −88.0 (5)
C12—N1—C13—C14 −97.4 (5) C20—N2—C32—C33 93.2 (5)
N1—C13—C14—C19 −101.7 (4) N2—C32—C33—C38 −49.9 (5)
N1—C13—C14—C15 81.2 (5) N2—C32—C33—C34 133.0 (4)
C19—C14—C15—C16 −0.5 (6) C38—C33—C34—C35 −0.5 (6)
C13—C14—C15—C16 176.7 (3) C32—C33—C34—C35 176.7 (4)
C14—C15—C16—C17 −0.7 (6) C33—C34—C35—C36 −0.3 (6)
C15—C16—C17—C18 1.1 (6) C34—C35—C36—C37 1.7 (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—C19 179.5 (3) Br6—C36—C37—C38 176.4 (3)
C17—C18—C19—C14 −0.9 (6) C36—C37—C38—C33 1.3 (6)
C15—C14—C19—C18 1.3 (6) C34—C33—C38—C37 −0.1 (6)
C13—C14—C19—C18 −175.9 (3) C32—C33—C38—C37 −177.2 (4)
Open in a new tab

Footnotes

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

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. Borzatta, V. & Carrozza, P. (1991). European Patent EP 0 462 069.
  3. Buu-Hoï, N. P. & Royer, R. (1950). J. Org. Chem.15, 123–130.
  4. Caulfield, T., Cherrier, M. P., Combeau, C. & Mailliet, P. (2002). European Patent No. 1 253 141.
  5. Cui, J., Duan, M. & Cai, L. (2009). Acta Cryst. E65, o215. [DOI] [PMC free article] [PubMed]
  6. Duan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005a). Fine Chem.22, 39–40, 52.
  7. Duan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005b). Fine Chem.22, 52.
  8. Harfenist, M. & Joyner, C. T. (1983). US Patent No. 4 379 160.
  9. Harper, R. W., Lin, H. S. & Richett, M. E. (2002). World Patent No. 02 079 154.
  10. Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku/MSC, The Woodlands, Texas,.
  11. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  12. 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/S1600536808042827/sj2546sup1.cif

e-65-0o216-sup1.cif (26.8KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042827/sj2546Isup2.hkl

e-65-0o216-Isup2.hkl (382.8KB, 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

RESOURCES