9-(4-Bromo­phen­yl)-3,6-di-tert-butyl-9H-carbazole

Zhang, J.-Y.; Zhang, W.-Y.

doi:10.1107/S1600536811047386

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3307

https://doi.org/10.1107/S1600536811047386

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9-(4-Bromophenyl)-3,6-di-tert-butyl-9H-carbazole

Jing-Ya Zhang ^a ^* and Wei-Yi Zhang ^b

^aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bDepartment of Obstetrics and Gynecology, The First Affiliated Hospital of Henan University of Traditional Chinese Medicine, Zhengzhou 450003, People's Republic of China
^*Correspondence e-mail: zhangjy_2002@163.com

(Received 23 October 2011; accepted 9 November 2011; online 16 November 2011)

The asymmetric unit of the title compound, C₂₆H₂₈BrN, contains two independent molecules in which the carbazole rings are almost planar, with r.m.s. deviations of 0.0212 (1) and 0.0229 (1) Å. The dihedral angles between the carbazole ring system and the pendent benzene ring are 60.5 (1) and 56.3 (1)° in the two molecules. In the crystal, molecules are linked into chains along the b axis by C—H⋯π interactions.

Related literature

For background to the applications of the title compound, see: Wang et al. (2008 ). For the synthesis of the title compound, see: Weber et al. (2011 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₆H₂₈BrN
M_r = 434.40
Triclinic, $[P \overline 1]$
a = 5.9300 (12) Å
b = 17.634 (4) Å
c = 22.343 (5) Å
α = 100.38 (3)°
β = 95.13 (3)°
γ = 99.32 (3)°
V = 2250.8 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.84 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.710, T_max = 0.838
9130 measured reflections
8267 independent reflections
3724 reflections with I > 2σ(I)
R_int = 0.054
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.160
S = 1.00
8267 reflections
505 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg11 and Cg8 are the centroids of the C7–C12, C47–C52 and N2/C27/C32–C34 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯Cg3ⁱ	0.93	2.75	3.544 (8)	144
C25—H25A⋯Cg11ⁱⁱ	0.93	2.92	3.511 (7)	123
C52—H52A⋯Cg8ⁱⁱⁱ	0.93	2.95	3.591 (8)	127
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ); 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: https://doi.org/10.1107/S1600536811047386/vm2131sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047386/vm2131Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047386/vm2131Isup3.cml

checkCIF report

Comment top

The title compound, 9-(4-bromophenyl)-3,6-di-tert-butyl-9H-carbazole, is an important intermediate, which can be utilized to synthesize organic semiconductors and conjugated polymers (Wang et al. , 2008). Here we report here its crystal structure (Fig. 1).

The two molecules in the asymmetric unit have the same conformation (r.m.s. deviation 0.2092 Å for all non-H atoms fitted) . The bond lengths and angles are within normal ranges (Allen et al., 1987). The carbazole rings are almost planar. The dihedral angles of the rings A(C1—C6/N1/C7—C12), B(C21—C26), C(C27—C32/N2/C33—C38), D(C47—C52) are: A/B = 60.5 (1)°, C/D = 56.3 (1)°.

In the crystal packing, there are not classic hydrogen bonds found. The molecular chains are linked by C—H···π interactions (Table 1) to give a three-dimensional network, which seems to be very effective in the stabilization of the crystal structure.

Related literature top

For background to the applications of the title compound, see: Wang et al. (2008). For the synthesis of the title compound, see: Weber et al. (2011). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I) was prepared by a method reported in literature (Weber et al. , 2011). The crystals were obtained by dissolving (I) (0.5 g) in methanol (50 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Structure description top

For background to the applications of the title compound, see: Wang et al. (2008). For the synthesis of the title compound, see: Weber et al. (2011). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo,1995); 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. Molecular structure of (I) with the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram of (I) showing C—H···π interactions as dashed lines.

9-(4-Bromophenyl)-3,6-di-tert-butyl-9H-carbazole top

Crystal data top

C₂₆H₂₈BrN	Z = 4
M_r = 434.40	F(000) = 904
Triclinic, P1	D_x = 1.282 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9300 (12) Å	Cell parameters from 25 reflections
b = 17.634 (4) Å	θ = 10–13°
c = 22.343 (5) Å	µ = 1.84 mm⁻¹
α = 100.38 (3)°	T = 293 K
β = 95.13 (3)°	Block, colourless
γ = 99.32 (3)°	0.20 × 0.10 × 0.10 mm
V = 2250.8 (8) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	3724 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 25.4°, θ_min = 1.2°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = −21→20
T_min = 0.710, T_max = 0.838	l = −26→26
9130 measured reflections	3 standard reflections every 200 reflections
8267 independent reflections	intensity decay: 1%

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.059P)²] where P = (F_o² + 2F_c²)/3
8267 reflections	(Δ/σ)_max < 0.001
505 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₂₆H₂₈BrN	γ = 99.32 (3)°
M_r = 434.40	V = 2250.8 (8) Å³
Triclinic, P1	Z = 4
a = 5.9300 (12) Å	Mo Kα radiation
b = 17.634 (4) Å	µ = 1.84 mm⁻¹
c = 22.343 (5) Å	T = 293 K
α = 100.38 (3)°	0.20 × 0.10 × 0.10 mm
β = 95.13 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3724 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.054
T_min = 0.710, T_max = 0.838	3 standard reflections every 200 reflections
9130 measured reflections	intensity decay: 1%
8267 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.00	Δρ_max = 0.52 e Å⁻³
8267 reflections	Δρ_min = −0.54 e Å⁻³
505 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	1.18728 (13)	0.51528 (4)	0.36422 (3)	0.0683 (3)
N1	0.6647 (9)	0.7449 (3)	0.2618 (2)	0.0568 (15)
C1	0.5559 (11)	0.7335 (3)	0.2012 (3)	0.0503 (17)
C2	0.5832 (11)	0.6807 (3)	0.1511 (3)	0.0556 (18)
H2A	0.6799	0.6445	0.1535	0.067*
C3	0.4579 (13)	0.6840 (4)	0.0960 (3)	0.066 (2)
H3A	0.4754	0.6491	0.0609	0.079*
C4	0.3087 (11)	0.7362 (4)	0.0903 (3)	0.0546 (17)
C5	0.2891 (11)	0.7887 (3)	0.1427 (3)	0.0549 (18)
H5A	0.1913	0.8246	0.1405	0.066*
C6	0.4127 (10)	0.7888 (3)	0.1984 (3)	0.0472 (16)
C7	0.4345 (11)	0.8367 (3)	0.2589 (3)	0.0505 (17)
C8	0.5856 (11)	0.8078 (3)	0.2972 (3)	0.0523 (17)
C9	0.3366 (11)	0.9001 (3)	0.2840 (3)	0.0480 (16)
H9A	0.2386	0.9210	0.2592	0.058*
C10	0.3866 (12)	0.9320 (4)	0.3466 (3)	0.0553 (18)
C11	0.5337 (13)	0.8995 (4)	0.3825 (3)	0.070 (2)
H11A	0.5652	0.9209	0.4242	0.084*
C12	0.6350 (12)	0.8375 (4)	0.3596 (3)	0.0610 (19)
H12A	0.7317	0.8165	0.3847	0.073*
C13	0.1759 (12)	0.7339 (4)	0.0287 (3)	0.0584 (18)
C14	0.0161 (13)	0.7946 (4)	0.0318 (3)	0.084 (3)
H14A	−0.0921	0.7849	0.0602	0.127*
H14B	−0.0654	0.7905	−0.0081	0.127*
H14C	0.1061	0.8463	0.0451	0.127*
C15	0.3463 (15)	0.7520 (5)	−0.0174 (4)	0.113 (3)
H15A	0.4463	0.7142	−0.0212	0.169*
H15B	0.4363	0.8036	−0.0031	0.169*
H15C	0.2621	0.7496	−0.0567	0.169*
C16	0.0283 (15)	0.6533 (4)	0.0045 (4)	0.103 (3)
H16A	−0.0786	0.6419	0.0329	0.154*
H16B	0.1253	0.6145	−0.0001	0.154*
H16C	−0.0548	0.6527	−0.0345	0.154*
C17	0.2911 (12)	1.0038 (4)	0.3755 (3)	0.0586 (18)
C18	0.4896 (15)	1.0737 (4)	0.3912 (4)	0.119 (3)
H18A	0.5515	1.0830	0.3544	0.178*
H18B	0.6077	1.0628	0.4190	0.178*
H18C	0.4344	1.1194	0.4102	0.178*
C19	0.1969 (14)	0.9909 (4)	0.4331 (3)	0.094 (3)
H19A	0.1380	1.0363	0.4509	0.140*
H19B	0.3169	0.9822	0.4615	0.140*
H19C	0.0750	0.9460	0.4242	0.140*
C20	0.0997 (14)	1.0215 (4)	0.3337 (3)	0.093 (3)
H20A	0.1563	1.0310	0.2963	0.139*
H20B	0.0469	1.0671	0.3537	0.139*
H20C	−0.0255	0.9776	0.3247	0.139*
C21	0.7872 (12)	0.6911 (4)	0.2852 (3)	0.0483 (16)
C22	1.0060 (13)	0.7177 (4)	0.3155 (3)	0.0626 (19)
H22A	1.0738	0.7700	0.3194	0.075*
C23	1.1281 (12)	0.6664 (4)	0.3407 (3)	0.065 (2)
H23A	1.2742	0.6842	0.3622	0.078*
C24	1.0248 (12)	0.5896 (4)	0.3323 (3)	0.0550 (18)
C25	0.8063 (12)	0.5632 (4)	0.3026 (3)	0.0608 (19)
H25A	0.7385	0.5108	0.2980	0.073*
C26	0.6872 (12)	0.6147 (3)	0.2794 (3)	0.0554 (18)
H26A	0.5379	0.5971	0.2598	0.066*
Br2	−0.10255 (13)	0.46827 (4)	0.85902 (4)	0.0709 (3)
N2	0.5597 (9)	0.7103 (3)	0.7642 (2)	0.0541 (14)
C27	0.5939 (11)	0.6989 (3)	0.7025 (3)	0.0484 (16)
C28	0.4698 (12)	0.6432 (4)	0.6522 (3)	0.0607 (19)
H28A	0.3398	0.6084	0.6568	0.073*
C29	0.5478 (12)	0.6425 (4)	0.5968 (3)	0.0621 (19)
H29A	0.4670	0.6062	0.5633	0.074*
C30	0.7458 (12)	0.6941 (4)	0.5872 (3)	0.0561 (18)
C31	0.8639 (12)	0.7489 (4)	0.6379 (3)	0.0591 (18)
H31A	0.9930	0.7842	0.6335	0.071*
C32	0.7872 (11)	0.7503 (3)	0.6948 (3)	0.0506 (17)
C33	0.8728 (11)	0.7983 (4)	0.7553 (3)	0.0508 (17)
C34	0.7351 (12)	0.7715 (4)	0.7960 (3)	0.0552 (18)
C35	1.0543 (12)	0.8605 (4)	0.7758 (3)	0.0601 (19)
H35A	1.1509	0.8773	0.7484	0.072*
C36	1.0928 (13)	0.8978 (4)	0.8369 (3)	0.0594 (19)
C37	0.9450 (13)	0.8687 (4)	0.8764 (3)	0.067 (2)
H37A	0.9663	0.8937	0.9174	0.080*
C38	0.7728 (13)	0.8061 (4)	0.8576 (3)	0.067 (2)
H38A	0.6822	0.7869	0.8854	0.081*
C39	0.8219 (12)	0.6878 (4)	0.5232 (3)	0.0601 (19)
C40	0.6346 (14)	0.7003 (5)	0.4787 (3)	0.102 (3)
H40A	0.6860	0.6975	0.4390	0.154*
H40B	0.5961	0.7510	0.4922	0.154*
H40C	0.5011	0.6605	0.4764	0.154*
C41	1.0313 (14)	0.7502 (5)	0.5216 (4)	0.109 (3)
H41A	1.0722	0.7449	0.4807	0.163*
H41B	1.1582	0.7436	0.5488	0.163*
H41C	0.9950	0.8013	0.5344	0.163*
C42	0.8816 (17)	0.6065 (5)	0.5030 (4)	0.122 (4)
H42A	0.9307	0.6022	0.4629	0.183*
H42B	0.7483	0.5671	0.5019	0.183*
H42C	1.0034	0.5992	0.5315	0.183*
C43	1.2806 (14)	0.9709 (4)	0.8600 (3)	0.072 (2)
C44	1.3953 (19)	0.9693 (6)	0.9218 (4)	0.159 (5)
H44A	1.4664	0.9238	0.9195	0.239*
H44B	1.2829	0.9674	0.9501	0.239*
H44C	1.5105	1.0157	0.9357	0.239*
C45	1.1659 (15)	1.0427 (4)	0.8613 (5)	0.149 (5)
H45A	1.2799	1.0895	0.8749	0.223*
H45B	1.0508	1.0414	0.8888	0.223*
H45C	1.0951	1.0424	0.8208	0.223*
C46	1.4614 (15)	0.9776 (5)	0.8171 (4)	0.106 (3)
H46A	1.5384	0.9335	0.8148	0.158*
H46B	1.5713	1.0251	0.8320	0.158*
H46C	1.3897	0.9786	0.7770	0.158*
C47	0.4023 (13)	0.6594 (3)	0.7889 (3)	0.0512 (17)
C48	0.4838 (12)	0.6231 (4)	0.8355 (3)	0.0593 (18)
H48A	0.6383	0.6354	0.8516	0.071*
C49	0.3324 (13)	0.5688 (3)	0.8573 (3)	0.0571 (18)
H49A	0.3858	0.5444	0.8879	0.069*
C50	0.1026 (12)	0.5510 (4)	0.8337 (3)	0.0575 (18)
C51	0.0264 (13)	0.5897 (4)	0.7890 (3)	0.0636 (19)
H51A	−0.1283	0.5786	0.7731	0.076*
C52	0.1742 (12)	0.6433 (4)	0.7683 (3)	0.0565 (18)
H52A	0.1179	0.6696	0.7393	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0855 (6)	0.0567 (5)	0.0698 (5)	0.0332 (4)	−0.0015 (4)	0.0187 (4)
N1	0.079 (4)	0.041 (3)	0.057 (4)	0.024 (3)	0.007 (3)	0.017 (3)
C1	0.068 (5)	0.046 (4)	0.038 (4)	0.017 (4)	0.002 (3)	0.008 (3)
C2	0.064 (5)	0.039 (4)	0.064 (5)	0.025 (3)	0.004 (4)	0.001 (3)
C3	0.090 (6)	0.053 (4)	0.054 (5)	0.019 (4)	0.014 (4)	−0.001 (4)
C4	0.065 (5)	0.051 (4)	0.050 (4)	0.016 (4)	0.010 (4)	0.008 (3)
C5	0.072 (5)	0.042 (4)	0.058 (5)	0.021 (4)	0.008 (4)	0.020 (3)
C6	0.056 (4)	0.042 (4)	0.049 (4)	0.019 (3)	0.011 (3)	0.013 (3)
C7	0.079 (5)	0.034 (3)	0.044 (4)	0.017 (3)	0.012 (4)	0.012 (3)
C8	0.070 (5)	0.035 (4)	0.051 (4)	0.012 (3)	−0.002 (4)	0.009 (3)
C9	0.060 (5)	0.043 (4)	0.044 (4)	0.019 (3)	0.010 (3)	0.007 (3)
C10	0.069 (5)	0.045 (4)	0.056 (5)	0.016 (4)	0.013 (4)	0.013 (3)
C11	0.092 (6)	0.062 (5)	0.053 (5)	0.026 (5)	−0.004 (4)	0.001 (4)
C12	0.083 (6)	0.044 (4)	0.058 (5)	0.018 (4)	−0.001 (4)	0.016 (4)
C13	0.061 (5)	0.057 (4)	0.052 (4)	0.006 (4)	−0.004 (4)	0.006 (3)
C14	0.116 (7)	0.094 (6)	0.049 (5)	0.046 (5)	−0.011 (4)	0.015 (4)
C15	0.132 (8)	0.147 (9)	0.080 (6)	0.048 (7)	0.047 (6)	0.041 (6)
C16	0.122 (8)	0.077 (6)	0.089 (6)	−0.007 (5)	−0.024 (6)	0.003 (5)
C17	0.067 (5)	0.054 (4)	0.057 (5)	0.025 (4)	0.005 (4)	0.005 (4)
C18	0.108 (8)	0.050 (5)	0.176 (10)	0.006 (5)	0.024 (7)	−0.029 (5)
C19	0.111 (7)	0.101 (6)	0.070 (6)	0.038 (6)	0.013 (5)	0.002 (5)
C20	0.120 (7)	0.068 (5)	0.094 (6)	0.051 (5)	0.005 (6)	−0.001 (4)
C21	0.055 (5)	0.043 (4)	0.050 (4)	0.013 (4)	−0.003 (3)	0.019 (3)
C22	0.073 (6)	0.041 (4)	0.077 (5)	0.012 (4)	0.008 (4)	0.018 (4)
C23	0.063 (5)	0.057 (5)	0.075 (5)	0.010 (4)	−0.005 (4)	0.019 (4)
C24	0.063 (5)	0.044 (4)	0.061 (4)	0.009 (4)	0.008 (4)	0.017 (3)
C25	0.062 (5)	0.042 (4)	0.083 (5)	0.018 (4)	0.005 (4)	0.019 (4)
C26	0.061 (5)	0.039 (4)	0.066 (5)	0.011 (4)	0.004 (4)	0.010 (3)
Br2	0.0782 (6)	0.0519 (5)	0.0866 (6)	0.0015 (4)	0.0305 (4)	0.0237 (4)
N2	0.065 (4)	0.045 (3)	0.048 (3)	−0.007 (3)	0.009 (3)	0.011 (3)
C27	0.054 (5)	0.039 (4)	0.050 (4)	0.002 (3)	0.007 (4)	0.009 (3)
C28	0.067 (5)	0.054 (4)	0.059 (5)	0.004 (4)	0.008 (4)	0.013 (4)
C29	0.080 (6)	0.042 (4)	0.062 (5)	0.011 (4)	0.011 (4)	0.002 (3)
C30	0.074 (5)	0.053 (4)	0.047 (4)	0.018 (4)	0.011 (4)	0.020 (4)
C31	0.075 (5)	0.055 (4)	0.048 (4)	0.006 (4)	0.003 (4)	0.018 (4)
C32	0.062 (5)	0.043 (4)	0.049 (4)	0.013 (4)	0.005 (4)	0.012 (3)
C33	0.053 (5)	0.043 (4)	0.060 (5)	0.007 (4)	0.013 (4)	0.017 (4)
C34	0.068 (5)	0.046 (4)	0.046 (4)	0.001 (4)	0.000 (4)	0.008 (3)
C35	0.065 (5)	0.058 (4)	0.060 (5)	0.006 (4)	0.008 (4)	0.023 (4)
C36	0.080 (6)	0.039 (4)	0.057 (5)	0.007 (4)	−0.007 (4)	0.017 (4)
C37	0.076 (6)	0.048 (4)	0.071 (5)	0.005 (4)	0.006 (4)	0.005 (4)
C38	0.093 (6)	0.055 (4)	0.052 (5)	0.004 (4)	0.016 (4)	0.011 (4)
C39	0.064 (5)	0.072 (5)	0.048 (4)	0.025 (4)	0.009 (4)	0.008 (4)
C40	0.087 (7)	0.153 (8)	0.075 (6)	0.030 (6)	0.009 (5)	0.035 (6)
C41	0.093 (7)	0.136 (8)	0.089 (6)	−0.008 (6)	0.030 (5)	0.018 (6)
C42	0.193 (11)	0.110 (7)	0.090 (7)	0.079 (7)	0.053 (7)	0.026 (6)
C43	0.084 (6)	0.058 (5)	0.060 (5)	−0.006 (4)	−0.007 (4)	0.003 (4)
C44	0.190 (12)	0.152 (10)	0.096 (8)	−0.060 (8)	−0.053 (8)	0.035 (7)
C45	0.103 (8)	0.039 (5)	0.284 (14)	−0.003 (5)	0.020 (9)	−0.004 (7)
C46	0.107 (7)	0.095 (7)	0.101 (7)	−0.024 (5)	0.012 (6)	0.020 (5)
C47	0.071 (5)	0.036 (4)	0.053 (4)	0.021 (4)	0.018 (4)	0.014 (3)
C48	0.061 (5)	0.062 (5)	0.062 (5)	0.022 (4)	0.016 (4)	0.017 (4)
C49	0.072 (6)	0.048 (4)	0.060 (5)	0.017 (4)	0.017 (4)	0.023 (3)
C50	0.056 (5)	0.061 (5)	0.058 (5)	0.018 (4)	0.021 (4)	0.006 (4)
C51	0.070 (5)	0.063 (5)	0.061 (5)	0.011 (4)	0.022 (4)	0.015 (4)
C52	0.059 (5)	0.055 (4)	0.065 (5)	0.026 (4)	0.007 (4)	0.024 (4)

Geometric parameters (Å, º) top

Br1—C24	1.944 (6)	Br2—C50	1.944 (7)
N1—C1	1.411 (7)	N2—C27	1.395 (7)
N1—C8	1.413 (7)	N2—C47	1.405 (7)
N1—C21	1.427 (7)	N2—C34	1.407 (7)
C1—C2	1.361 (8)	C27—C32	1.386 (8)
C1—C6	1.398 (7)	C27—C28	1.411 (8)
C2—C3	1.396 (8)	C28—C29	1.357 (8)
C2—H2A	0.9300	C28—H28A	0.9300
C3—C4	1.391 (8)	C29—C30	1.422 (9)
C3—H3A	0.9300	C29—H29A	0.9300
C4—C5	1.382 (8)	C30—C31	1.397 (8)
C4—C13	1.514 (8)	C30—C39	1.528 (8)
C5—C6	1.387 (8)	C31—C32	1.387 (8)
C5—H5A	0.9300	C31—H31A	0.9300
C6—C7	1.441 (8)	C32—C33	1.457 (8)
C7—C9	1.394 (7)	C33—C34	1.372 (8)
C7—C8	1.402 (8)	C33—C35	1.385 (8)
C8—C12	1.385 (8)	C34—C38	1.383 (8)
C9—C10	1.398 (8)	C35—C36	1.386 (8)
C9—H9A	0.9300	C35—H35A	0.9300
C10—C11	1.391 (8)	C36—C37	1.402 (9)
C10—C17	1.530 (8)	C36—C43	1.536 (9)
C11—C12	1.372 (8)	C37—C38	1.352 (9)
C11—H11A	0.9300	C37—H37A	0.9300
C12—H12A	0.9300	C38—H38A	0.9300
C13—C16	1.521 (9)	C39—C40	1.494 (9)
C13—C14	1.536 (8)	C39—C41	1.527 (9)
C13—C15	1.544 (9)	C39—C42	1.531 (9)
C14—H14A	0.9600	C40—H40A	0.9600
C14—H14B	0.9600	C40—H40B	0.9600
C14—H14C	0.9600	C40—H40C	0.9600
C15—H15A	0.9600	C41—H41A	0.9600
C15—H15B	0.9600	C41—H41B	0.9600
C15—H15C	0.9600	C41—H41C	0.9600
C16—H16A	0.9600	C42—H42A	0.9600
C16—H16B	0.9600	C42—H42B	0.9600
C16—H16C	0.9600	C42—H42C	0.9600
C17—C19	1.487 (9)	C43—C44	1.491 (10)
C17—C20	1.513 (9)	C43—C46	1.505 (10)
C17—C18	1.526 (9)	C43—C45	1.530 (10)
C18—H18A	0.9600	C44—H44A	0.9600
C18—H18B	0.9600	C44—H44B	0.9600
C18—H18C	0.9600	C44—H44C	0.9600
C19—H19A	0.9600	C45—H45A	0.9600
C19—H19B	0.9600	C45—H45B	0.9600
C19—H19C	0.9600	C45—H45C	0.9600
C20—H20A	0.9600	C46—H46A	0.9600
C20—H20B	0.9600	C46—H46B	0.9600
C20—H20C	0.9600	C46—H46C	0.9600
C21—C26	1.359 (8)	C47—C52	1.356 (8)
C21—C22	1.376 (8)	C47—C48	1.406 (8)
C22—C23	1.407 (8)	C48—C49	1.390 (8)
C22—H22A	0.9300	C48—H48A	0.9300
C23—C24	1.365 (8)	C49—C50	1.381 (8)
C23—H23A	0.9300	C49—H49A	0.9300
C24—C25	1.370 (8)	C50—C51	1.388 (8)
C25—C26	1.379 (8)	C51—C52	1.356 (8)
C25—H25A	0.9300	C51—H51A	0.9300
C26—H26A	0.9300	C52—H52A	0.9300

C1—N1—C8	107.6 (5)	C27—N2—C47	124.0 (5)
C1—N1—C21	125.1 (5)	C27—N2—C34	107.1 (5)
C8—N1—C21	125.8 (5)	C47—N2—C34	128.0 (5)
C2—C1—C6	122.7 (6)	C32—C27—N2	109.9 (5)
C2—C1—N1	128.3 (6)	C32—C27—C28	120.5 (6)
C6—C1—N1	108.9 (5)	N2—C27—C28	129.5 (6)
C1—C2—C3	116.2 (6)	C29—C28—C27	117.3 (6)
C1—C2—H2A	121.9	C29—C28—H28A	121.3
C3—C2—H2A	121.9	C27—C28—H28A	121.3
C4—C3—C2	124.1 (6)	C28—C29—C30	123.8 (6)
C4—C3—H3A	118.0	C28—C29—H29A	118.1
C2—C3—H3A	118.0	C30—C29—H29A	118.1
C5—C4—C3	117.0 (6)	C31—C30—C29	117.5 (6)
C5—C4—C13	122.9 (6)	C31—C30—C39	122.7 (6)
C3—C4—C13	120.1 (6)	C29—C30—C39	119.8 (6)
C4—C5—C6	121.2 (6)	C32—C31—C30	119.5 (6)
C4—C5—H5A	119.4	C32—C31—H31A	120.2
C6—C5—H5A	119.4	C30—C31—H31A	120.2
C5—C6—C1	118.7 (6)	C27—C32—C31	121.3 (6)
C5—C6—C7	133.9 (6)	C27—C32—C33	106.1 (6)
C1—C6—C7	107.4 (5)	C31—C32—C33	132.5 (6)
C9—C7—C8	118.8 (6)	C34—C33—C35	119.9 (6)
C9—C7—C6	133.8 (6)	C34—C33—C32	107.4 (6)
C8—C7—C6	107.4 (5)	C35—C33—C32	132.7 (6)
C12—C8—C7	122.8 (6)	C33—C34—C38	121.0 (7)
C12—C8—N1	128.6 (6)	C33—C34—N2	109.4 (6)
C7—C8—N1	108.6 (5)	C38—C34—N2	129.6 (6)
C7—C9—C10	119.5 (6)	C33—C35—C36	120.4 (6)
C7—C9—H9A	120.2	C33—C35—H35A	119.8
C10—C9—H9A	120.2	C36—C35—H35A	119.8
C11—C10—C9	118.9 (6)	C35—C36—C37	117.3 (6)
C11—C10—C17	119.9 (6)	C35—C36—C43	121.6 (7)
C9—C10—C17	121.2 (6)	C37—C36—C43	121.0 (7)
C12—C11—C10	123.5 (6)	C38—C37—C36	123.1 (7)
C12—C11—H11A	118.2	C38—C37—H37A	118.5
C10—C11—H11A	118.2	C36—C37—H37A	118.5
C11—C12—C8	116.5 (6)	C37—C38—C34	118.2 (7)
C11—C12—H12A	121.8	C37—C38—H38A	120.9
C8—C12—H12A	121.8	C34—C38—H38A	120.9
C4—C13—C16	110.3 (6)	C40—C39—C41	106.4 (6)
C4—C13—C14	112.5 (5)	C40—C39—C30	110.4 (6)
C16—C13—C14	107.8 (6)	C41—C39—C30	112.0 (6)
C4—C13—C15	109.5 (6)	C40—C39—C42	110.0 (7)
C16—C13—C15	109.1 (6)	C41—C39—C42	109.1 (7)
C14—C13—C15	107.5 (6)	C30—C39—C42	109.0 (6)
C13—C14—H14A	109.5	C39—C40—H40A	109.5
C13—C14—H14B	109.5	C39—C40—H40B	109.5
H14A—C14—H14B	109.5	H40A—C40—H40B	109.5
C13—C14—H14C	109.5	C39—C40—H40C	109.5
H14A—C14—H14C	109.5	H40A—C40—H40C	109.5
H14B—C14—H14C	109.5	H40B—C40—H40C	109.5
C13—C15—H15A	109.5	C39—C41—H41A	109.5
C13—C15—H15B	109.5	C39—C41—H41B	109.5
H15A—C15—H15B	109.5	H41A—C41—H41B	109.5
C13—C15—H15C	109.5	C39—C41—H41C	109.5
H15A—C15—H15C	109.5	H41A—C41—H41C	109.5
H15B—C15—H15C	109.5	H41B—C41—H41C	109.5
C13—C16—H16A	109.5	C39—C42—H42A	109.5
C13—C16—H16B	109.5	C39—C42—H42B	109.5
H16A—C16—H16B	109.5	H42A—C42—H42B	109.5
C13—C16—H16C	109.5	C39—C42—H42C	109.5
H16A—C16—H16C	109.5	H42A—C42—H42C	109.5
H16B—C16—H16C	109.5	H42B—C42—H42C	109.5
C19—C17—C20	107.6 (6)	C44—C43—C46	108.6 (8)
C19—C17—C18	108.5 (6)	C44—C43—C45	111.4 (8)
C20—C17—C18	110.0 (6)	C46—C43—C45	106.5 (7)
C19—C17—C10	110.2 (6)	C44—C43—C36	110.7 (6)
C20—C17—C10	112.6 (6)	C46—C43—C36	112.0 (6)
C18—C17—C10	107.9 (6)	C45—C43—C36	107.5 (6)
C17—C18—H18A	109.5	C43—C44—H44A	109.5
C17—C18—H18B	109.5	C43—C44—H44B	109.5
H18A—C18—H18B	109.5	H44A—C44—H44B	109.5
C17—C18—H18C	109.5	C43—C44—H44C	109.5
H18A—C18—H18C	109.5	H44A—C44—H44C	109.5
H18B—C18—H18C	109.5	H44B—C44—H44C	109.5
C17—C19—H19A	109.5	C43—C45—H45A	109.5
C17—C19—H19B	109.5	C43—C45—H45B	109.5
H19A—C19—H19B	109.5	H45A—C45—H45B	109.5
C17—C19—H19C	109.5	C43—C45—H45C	109.5
H19A—C19—H19C	109.5	H45A—C45—H45C	109.5
H19B—C19—H19C	109.5	H45B—C45—H45C	109.5
C17—C20—H20A	109.5	C43—C46—H46A	109.5
C17—C20—H20B	109.5	C43—C46—H46B	109.5
H20A—C20—H20B	109.5	H46A—C46—H46B	109.5
C17—C20—H20C	109.5	C43—C46—H46C	109.5
H20A—C20—H20C	109.5	H46A—C46—H46C	109.5
H20B—C20—H20C	109.5	H46B—C46—H46C	109.5
C26—C21—C22	120.0 (6)	C52—C47—N2	121.9 (6)
C26—C21—N1	120.6 (6)	C52—C47—C48	118.9 (6)
C22—C21—N1	119.3 (6)	N2—C47—C48	119.2 (7)
C21—C22—C23	120.5 (6)	C49—C48—C47	119.7 (7)
C21—C22—H22A	119.7	C49—C48—H48A	120.1
C23—C22—H22A	119.7	C47—C48—H48A	120.1
C24—C23—C22	117.8 (7)	C50—C49—C48	120.1 (6)
C24—C23—H23A	121.1	C50—C49—H49A	120.0
C22—C23—H23A	121.1	C48—C49—H49A	120.0
C23—C24—C25	121.7 (6)	C49—C50—C51	118.8 (6)
C23—C24—Br1	119.8 (5)	C49—C50—Br2	119.9 (5)
C25—C24—Br1	118.5 (5)	C51—C50—Br2	121.2 (6)
C24—C25—C26	119.7 (6)	C52—C51—C50	121.0 (7)
C24—C25—H25A	120.1	C52—C51—H51A	119.5
C26—C25—H25A	120.1	C50—C51—H51A	119.5
C21—C26—C25	120.2 (6)	C47—C52—C51	121.4 (6)
C21—C26—H26A	119.9	C47—C52—H52A	119.3
C25—C26—H26A	119.9	C51—C52—H52A	119.3

C8—N1—C1—C2	178.5 (7)	C47—N2—C27—C32	−169.1 (6)
C21—N1—C1—C2	−15.0 (11)	C34—N2—C27—C32	0.9 (7)
C8—N1—C1—C6	0.6 (7)	C47—N2—C27—C28	7.9 (10)
C21—N1—C1—C6	167.1 (6)	C34—N2—C27—C28	177.9 (6)
C6—C1—C2—C3	−0.5 (10)	C32—C27—C28—C29	0.0 (9)
N1—C1—C2—C3	−178.1 (6)	N2—C27—C28—C29	−176.7 (6)
C1—C2—C3—C4	−1.0 (10)	C27—C28—C29—C30	0.3 (10)
C2—C3—C4—C5	1.4 (10)	C28—C29—C30—C31	−0.7 (10)
C2—C3—C4—C13	−178.5 (6)	C28—C29—C30—C39	179.1 (6)
C3—C4—C5—C6	−0.2 (10)	C29—C30—C31—C32	0.9 (9)
C13—C4—C5—C6	179.7 (6)	C39—C30—C31—C32	−178.9 (6)
C4—C5—C6—C1	−1.1 (9)	N2—C27—C32—C31	177.5 (5)
C4—C5—C6—C7	177.4 (7)	C28—C27—C32—C31	0.2 (9)
C2—C1—C6—C5	1.5 (10)	N2—C27—C32—C33	−2.1 (7)
N1—C1—C6—C5	179.6 (5)	C28—C27—C32—C33	−179.4 (6)
C2—C1—C6—C7	−177.3 (6)	C30—C31—C32—C27	−0.7 (9)
N1—C1—C6—C7	0.7 (7)	C30—C31—C32—C33	178.8 (6)
C5—C6—C7—C9	1.3 (13)	C27—C32—C33—C34	2.6 (7)
C1—C6—C7—C9	179.9 (7)	C31—C32—C33—C34	−177.0 (7)
C5—C6—C7—C8	179.6 (7)	C27—C32—C33—C35	−177.6 (7)
C1—C6—C7—C8	−1.7 (7)	C31—C32—C33—C35	2.8 (12)
C9—C7—C8—C12	2.5 (10)	C35—C33—C34—C38	0.7 (10)
C6—C7—C8—C12	−176.1 (6)	C32—C33—C34—C38	−179.5 (6)
C9—C7—C8—N1	−179.2 (5)	C35—C33—C34—N2	178.0 (5)
C6—C7—C8—N1	2.1 (7)	C32—C33—C34—N2	−2.1 (7)
C1—N1—C8—C12	176.4 (7)	C27—N2—C34—C33	0.8 (7)
C21—N1—C8—C12	10.0 (11)	C47—N2—C34—C33	170.3 (6)
C1—N1—C8—C7	−1.7 (7)	C27—N2—C34—C38	177.9 (7)
C21—N1—C8—C7	−168.1 (6)	C47—N2—C34—C38	−12.6 (11)
C8—C7—C9—C10	−1.4 (9)	C34—C33—C35—C36	−2.4 (10)
C6—C7—C9—C10	176.8 (7)	C32—C33—C35—C36	177.8 (6)
C7—C9—C10—C11	0.0 (10)	C33—C35—C36—C37	1.4 (10)
C7—C9—C10—C17	177.3 (6)	C33—C35—C36—C43	−175.2 (6)
C9—C10—C11—C12	0.4 (11)	C35—C36—C37—C38	1.3 (11)
C17—C10—C11—C12	−176.9 (7)	C43—C36—C37—C38	177.9 (6)
C10—C11—C12—C8	0.6 (11)	C36—C37—C38—C34	−2.9 (11)
C7—C8—C12—C11	−2.1 (10)	C33—C34—C38—C37	2.0 (10)
N1—C8—C12—C11	−180.0 (6)	N2—C34—C38—C37	−174.9 (6)
C5—C4—C13—C16	−121.7 (7)	C31—C30—C39—C40	−120.9 (7)
C3—C4—C13—C16	58.2 (9)	C29—C30—C39—C40	59.3 (8)
C5—C4—C13—C14	−1.2 (9)	C31—C30—C39—C41	−2.6 (9)
C3—C4—C13—C14	178.7 (6)	C29—C30—C39—C41	177.6 (6)
C5—C4—C13—C15	118.2 (7)	C31—C30—C39—C42	118.2 (7)
C3—C4—C13—C15	−61.9 (8)	C29—C30—C39—C42	−61.6 (8)
C11—C10—C17—C19	−48.6 (9)	C35—C36—C43—C44	−142.2 (8)
C9—C10—C17—C19	134.1 (7)	C37—C36—C43—C44	41.3 (10)
C11—C10—C17—C20	−168.7 (7)	C35—C36—C43—C46	−20.8 (10)
C9—C10—C17—C20	14.0 (10)	C37—C36—C43—C46	162.7 (7)
C11—C10—C17—C18	69.7 (9)	C35—C36—C43—C45	95.9 (9)
C9—C10—C17—C18	−107.6 (7)	C37—C36—C43—C45	−80.6 (9)
C1—N1—C21—C26	−52.7 (9)	C27—N2—C47—C52	−58.5 (9)
C8—N1—C21—C26	111.3 (7)	C34—N2—C47—C52	133.7 (7)
C1—N1—C21—C22	129.1 (7)	C27—N2—C47—C48	120.4 (7)
C8—N1—C21—C22	−66.8 (9)	C34—N2—C47—C48	−47.4 (9)
C26—C21—C22—C23	0.0 (10)	C52—C47—C48—C49	3.2 (9)
N1—C21—C22—C23	178.2 (6)	N2—C47—C48—C49	−175.8 (6)
C21—C22—C23—C24	1.9 (10)	C47—C48—C49—C50	−0.5 (9)
C22—C23—C24—C25	−2.5 (10)	C48—C49—C50—C51	−1.4 (9)
C22—C23—C24—Br1	178.6 (5)	C48—C49—C50—Br2	174.4 (5)
C23—C24—C25—C26	1.1 (10)	C49—C50—C51—C52	0.7 (10)
Br1—C24—C25—C26	−179.9 (5)	Br2—C50—C51—C52	−175.1 (5)
C22—C21—C26—C25	−1.5 (10)	N2—C47—C52—C51	174.9 (6)
N1—C21—C26—C25	−179.6 (6)	C48—C47—C52—C51	−4.0 (10)
C24—C25—C26—C21	0.9 (10)	C50—C51—C52—C47	2.1 (10)

Hydrogen-bond geometry (Å, º) top

Cg3, Cg11 and Cg8 are the centroids of the C7–C12, C47–C52 and N2/C27/C32–C34 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Cg3ⁱ	0.93	2.75	3.544 (8)	144
C25—H25A···Cg11ⁱⁱ	0.93	2.92	3.511 (7)	123
C52—H52A···Cg8ⁱⁱⁱ	0.93	2.95	3.591 (8)	127

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₈BrN
M_r	434.40
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.9300 (12), 17.634 (4), 22.343 (5)
α, β, γ (°)	100.38 (3), 95.13 (3), 99.32 (3)
V (Å³)	2250.8 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.84
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.710, 0.838
No. of measured, independent and observed [I > 2σ(I)] reflections	9130, 8267, 3724
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.160, 1.00
No. of reflections	8267
No. of parameters	505
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.54

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg3, Cg11 and Cg8 are the centroids of the C7–C12, C47–C52 and N2/C27/C32–C34 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Cg3ⁱ	0.93	2.75	3.544 (8)	144
C25—H25A···Cg11ⁱⁱ	0.93	2.92	3.511 (7)	123
C52—H52A···Cg8ⁱⁱⁱ	0.93	2.95	3.591 (8)	127

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z.

Acknowledgements

This work was supported by the Fund of Henan Chinese Medicine (BSJJ2009–29). The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

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. CSD CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, C. S., Batsanov, A. S., West, K. & Bryce, M. R. (2008). Org. Lett. 14, 3069–3072. Web of Science CSD CrossRef Google Scholar
Weber, L. H. J., Boehling, L., Chrostowska, A., Dargelos, A., Stammler, H. G. & Neumann, B. (2011). Eur. J. Inorg. Chem. 20, 3091–3101. Web of Science CSD CrossRef Google Scholar

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