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

Cui, J.; Duan, M.; Cai, L.

doi:10.1107/S1600536808042827

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o216

doi:10.1107/S1600536808042827

Open

access

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

Jian-lan Cui,^a ^* Mei Duan ^b and Liu-qing Cai ^a

^aSchool of Chemical Engineering and Environment, North University of China, Taiyuan 030051, People's Republic of China, and ^bShanxi Provincial People's Hospital, Taiyuan 030012, People's Republic of China
^*Correspondence e-mail: cuijianlan2005@yahoo.com.cn

(Received 6 October 2008; accepted 16 December 2008; online 8 January 2009)

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 ).

Experimental

Crystal data

C₁₉H₁₂Br₃N
M_r = 494.00
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.103
S = 1.02
7824 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042827/sj2546sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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).

Experimental top

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).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top

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

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

Crystal data top

C₁₉H₁₂Br₃N	F(000) = 1904
M_r = 494.00	D_x = 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

Data collection top

Rigaku Saturn diffractometer	7824 independent reflections
Radiation source: rotating anode	6058 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.054
ω scans	θ_max = 27.9°, θ_min = 1.6°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −12→10
T_min = 0.591, T_max = 0.867	k = −20→22
25134 measured reflections	l = −26→26

Refinement top

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(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
7824 reflections	(Δ/σ)_max = 0.002
415 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

C₁₉H₁₂Br₃N	V = 3288.1 (11) Å³
M_r = 494.00	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4784 (19) Å	µ = 7.36 mm⁻¹
b = 17.132 (3) Å	T = 113 K
c = 20.456 (4) Å	0.08 × 0.02 × 0.02 mm
β = 98.16 (3)°

Data collection top

Rigaku Saturn diffractometer	7824 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	6058 reflections with I > 2σ(I)
T_min = 0.591, T_max = 0.867	R_int = 0.054
25134 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.02	Δρ_max = 0.62 e Å⁻³
7824 reflections	Δρ_min = −0.86 e Å⁻³
415 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂Br₃N
M_r	494.00
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	9.4784 (19), 17.132 (3), 20.456 (4)
β (°)	98.16 (3)
V (Å³)	3288.1 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	7.36
Crystal size (mm)	0.08 × 0.02 × 0.02

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.591, 0.867
No. of measured, independent and observed [I > 2σ(I)] reflections	25134, 7824, 6058
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.103, 1.02
No. of reflections	7824
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.86

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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. CrossRef Web of Science Google Scholar
Borzatta, V. & Carrozza, P. (1991). European Patent EP 0 462 069. Google Scholar
Buu-Hoï, N. P. & Royer, R. (1950). J. Org. Chem. 15, 123–130. CrossRef CAS Google Scholar
Caulfield, T., Cherrier, M. P., Combeau, C. & Mailliet, P. (2002). European Patent No. 1 253 141. Google Scholar
Cui, J., Duan, M. & Cai, L. (2009). Acta Cryst. E65, o215. Web of Science CSD CrossRef IUCr Journals Google Scholar
Duan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005a). Fine Chem. 22, 39–40, 52. Google Scholar
Duan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005b). Fine Chem. 22, 52. Google Scholar
Harfenist, M. & Joyner, C. T. (1983). US Patent No. 4 379 160. Google Scholar
Harper, R. W., Lin, H. S. & Richett, M. E. (2002). World Patent No. 02 079 154. Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas,. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith, K., James, D. M., Mistry, A. G., Bye, M. R. & Faulkner, D. J. (1992). Tetrahedron, 48, 7479–7488. CrossRef CAS Web of Science Google Scholar