9-Benzyl-3,6-dibromo-9H-carbazole

Duan, X.-M.; Huang, P.-M.; Zheng, P.-W.; Li, J.-S.

doi:10.1107/S1600536805029430

9-Benzyl-3,6-dibromo-9H-carbazole

X.-M. Duan, P.-M. Huang, P.-W. Zheng and J. Li

Two independent molecules comprise the asymmetric unit of the title compound, C₁₉H₁₃Br₂N, which was synthesized by N-alkylation of benzyl bromide with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar and forms a dihedral angle with the pendant phenyl ring of 66.0 (2)° [70.6 (2)° for the second molecule]. In the crystal structure, π–π interactions and weak C—H

Br interactions are observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029430/tk6261sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029430/tk6261Isup2.hkl Contains datablock I

CCDC reference: 287739

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.012 Å
R factor = 0.045
wR factor = 0.095
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  BR3     ..       3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  BR1     ..       3.01 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H25    ..  BR4     ..       2.97 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.40
           From the CIF: _reflns_number_total               5698
           Count of symmetry unique reflns         3318
           Completeness (_total/calc)            171.73%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2380
           Fraction of Friedel pairs measured     0.717
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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, the structure of 9-benzyl-3,6-dibromo-9H-carbazole (I), is reported which was synthesized by N-alkylation of benzyl bromide with 3,6-dibromo-9H-carbazole.

The asymmetric unit of (I) comprises two independent but similar molecules, Fig. 1. The carbazole ring in each is essentially planar, with mean deviations of 0.030 and 0.016 Å, respectively. The dihedral angles formed between the carbazole ring and the plane through the pendant phenyl ring is 66.0 (2)° [70.6 (2)° for the second molecule]. The C—Br distances fall in the range 1.903 (7) to 1.925 (8) Å, consistent with the literature (Allen et al., 1987). In the crystal structure, there are π-π interactions with the closest of these, 3.66 Å, is formed between the N1—C7 and C7—C12 rings of translationally related molecules [x, −1 + y, z]. In addition, there are C—H···Br interactions, as shown in Fig. 2 and detailed in Table 1.

Experimental top

The title compound was prepared according to the procedure of Duan et al. (2005). A solution of potassium hydroxide (7.0 g) in dimethylformamide (50 ml) was stirred at room temperature for 20 min. 3,6-Dibromo-carbazole (6.5 g, 20 mmol), prepared as in Smith et al. (1992) was added and the mixture stirred for a further 40 min. A solution of benzyl bromide (5.1 g, 30 mmol) in dimethylformamide (50 ml) was added dropwise with stirring. The resulting mixture was then stirred at room temperature for 10 h and poured into water (500 ml), yielding a white precipitate. The solid product was filtered off, washed with cold water and recrystallized from EtOH, giving crystals of (I). Yield: 7.51 g (90.5%); m.p. 430–432 K. ¹H NMR (DMSO-d₆, δ, p.p.m.) 5.6 (s, 2H), 7.2–7.6 (m, 9H), 8.5 (m, 2H); ¹³C NMR (DMSO-d₆, δ, p.p.m.) 46.8, 112.4, 112.9, 124.1, 124.5, 127.4, 128.3, 129.6, 129.9, 138.2, 140.2. Compound (I) (40 mg) was dissolved in mixture of chloroform (5 ml) and ethanol (5 ml) and the solution was kept at room temperature for 16 d. Natural evaporation of the solution gave colourless crystals suitable for X-Ray analysis.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. A view of the two independent molecules of (I); displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A portion of the crystal packing in (I), viewed down the b- direction. Dashed lines indicate C—H···Br interactions.

9-Benzyl-3,6-dibromo-9H-carbazole top

Crystal data top

C₁₉H₁₃Br₂N	F(000) = 1632
M_r = 415.12	D_x = 1.707 Mg m⁻³
Monoclinic, Cc	Melting point: 431(1) K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 39.113 (6) Å	Cell parameters from 1791 reflections
b = 4.5063 (7) Å	θ = 2.3–21.4°
c = 20.469 (3) Å	µ = 5.01 mm⁻¹
β = 116.449 (2)°	T = 294 K
V = 3230.1 (9) Å³	Rod, colourless
Z = 8	0.24 × 0.18 × 0.14 mm

Data collection top

CCD area detector diffractometer	5698 independent reflections
Radiation source: fine-focus sealed tube	3115 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.2°
Absorption correction: multi-scan SADABS (Bruker, 1997)	h = −48→44
T_min = 0.310, T_max = 0.496	k = −3→5
8574 measured reflections	l = −24→25

Refinement top

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0127P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max = 0.001
5698 reflections	Δρ_max = 0.34 e Å⁻³
397 parameters	Δρ_min = −0.40 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2371 Friedel pairs.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.010 (11)

Crystal data top

C₁₉H₁₃Br₂N	V = 3230.1 (9) Å³
M_r = 415.12	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 39.113 (6) Å	µ = 5.01 mm⁻¹
b = 4.5063 (7) Å	T = 294 K
c = 20.469 (3) Å	0.24 × 0.18 × 0.14 mm
β = 116.449 (2)°

Data collection top

CCD area detector diffractometer	5698 independent reflections
Absorption correction: multi-scan SADABS (Bruker, 1997)	3115 reflections with I > 2σ(I)
T_min = 0.310, T_max = 0.496	R_int = 0.043
8574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.095	Δρ_max = 0.34 e Å⁻³
S = 0.94	Δρ_min = −0.40 e Å⁻³
5698 reflections	Absolute structure: Flack (1983), 2371 Friedel pairs.
397 parameters	Absolute structure parameter: 0.010 (11)
2 restraints

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	0.83899 (2)	−0.05386 (19)	0.92134 (4)	0.0685 (3)
Br2	0.95821 (2)	1.06460 (18)	0.74368 (5)	0.0702 (3)
Br3	0.71044 (2)	0.4670 (2)	0.70656 (5)	0.0761 (3)
Br4	0.58665 (3)	0.48885 (19)	0.96645 (5)	0.0756 (3)
N1	0.81271 (16)	0.3578 (12)	0.6242 (3)	0.0420 (15)
N2	0.56825 (18)	1.0561 (13)	0.6868 (4)	0.0518 (17)
C1	0.8140 (2)	0.2487 (14)	0.6875 (4)	0.0349 (19)
C2	0.8468 (2)	0.3583 (16)	0.7476 (4)	0.0413 (19)
C3	0.8540 (2)	0.2714 (17)	0.8177 (4)	0.0452 (19)
H3	0.8752	0.3434	0.8580	0.054*
C4	0.8296 (2)	0.0802 (16)	0.8267 (4)	0.0451 (18)
C5	0.7970 (2)	−0.0274 (15)	0.7680 (4)	0.0494 (19)
H5	0.7806	−0.1554	0.7762	0.059*
C6	0.7889 (2)	0.0564 (14)	0.6975 (4)	0.0423 (18)
H6	0.7672	−0.0140	0.6578	0.051*
C7	0.8450 (2)	0.5360 (15)	0.6419 (4)	0.0391 (18)
C8	0.86589 (18)	0.5454 (14)	0.7181 (4)	0.0341 (17)
C9	0.8998 (2)	0.7069 (14)	0.7490 (4)	0.0456 (18)
H9	0.9142	0.7172	0.7993	0.055*
C10	0.9113 (2)	0.8507 (14)	0.7030 (5)	0.051 (2)
C11	0.8900 (2)	0.8387 (17)	0.6272 (5)	0.062 (2)
H11	0.8987	0.9368	0.5976	0.074*
C12	0.8567 (2)	0.6854 (15)	0.5964 (4)	0.0461 (18)
H12	0.8421	0.6810	0.5460	0.055*
C13	0.78659 (19)	0.2692 (16)	0.5498 (3)	0.0464 (18)
H13A	0.7743	0.0849	0.5520	0.056*
H13B	0.8014	0.2299	0.5234	0.056*
C14	0.75608 (19)	0.4919 (14)	0.5072 (3)	0.0399 (17)
C15	0.7288 (2)	0.5695 (16)	0.5294 (4)	0.0491 (19)
H15	0.7293	0.4839	0.5712	0.059*
C16	0.7006 (2)	0.774 (2)	0.4900 (5)	0.062 (2)
H16	0.6828	0.8310	0.5061	0.074*
C17	0.6992 (3)	0.8892 (19)	0.4283 (5)	0.072 (3)
H17	0.6798	1.0219	0.4013	0.086*
C18	0.7253 (3)	0.817 (2)	0.4044 (4)	0.065 (3)
H18	0.7240	0.9008	0.3617	0.078*
C19	0.7545 (2)	0.6153 (16)	0.4447 (4)	0.0475 (19)
H19	0.7727	0.5653	0.4290	0.057*
C20	0.5994 (2)	0.9402 (17)	0.6817 (4)	0.0435 (18)
C21	0.61892 (19)	0.7470 (15)	0.7412 (4)	0.0385 (17)
C22	0.65250 (19)	0.6069 (15)	0.7496 (4)	0.0456 (18)
H22	0.6660	0.4821	0.7889	0.055*
C23	0.6649 (2)	0.6603 (17)	0.6975 (4)	0.055 (2)
C24	0.6459 (3)	0.8433 (19)	0.6392 (4)	0.065 (2)
H24	0.6554	0.8731	0.6054	0.078*
C25	0.6125 (2)	0.9854 (17)	0.6301 (4)	0.057 (2)
H25	0.5993	1.1082	0.5902	0.068*
C26	0.5671 (2)	0.9419 (16)	0.7489 (4)	0.044 (2)
C27	0.5987 (2)	0.7515 (16)	0.7848 (4)	0.0399 (17)
C28	0.6040 (2)	0.6122 (15)	0.8495 (4)	0.0435 (18)
H28	0.6240	0.4799	0.8732	0.052*
C29	0.5788 (2)	0.6777 (17)	0.8765 (4)	0.055 (2)
C30	0.5472 (2)	0.8627 (17)	0.8410 (5)	0.057 (2)
H30	0.5301	0.8939	0.8605	0.068*
C31	0.5417 (2)	0.9963 (17)	0.7778 (4)	0.056 (2)
H31	0.5211	1.1234	0.7541	0.067*
C32	0.5397 (2)	1.2495 (16)	0.6329 (4)	0.057 (2)
H32A	0.5517	1.3668	0.6091	0.069*
H32B	0.5301	1.3852	0.6578	0.069*
C33	0.5066 (2)	1.0807 (16)	0.5758 (4)	0.057 (2)
C34	0.4725 (3)	1.0500 (19)	0.5790 (5)	0.075 (3)
H34	0.4694	1.1392	0.6171	0.090*
C35	0.4428 (3)	0.891 (2)	0.5276 (5)	0.084 (3)
H35	0.4200	0.8711	0.5313	0.101*
C36	0.4468 (3)	0.762 (2)	0.4708 (5)	0.079 (3)
H36	0.4265	0.6569	0.4355	0.095*
C37	0.4803 (3)	0.788 (2)	0.4656 (5)	0.084 (3)
H37	0.4832	0.6987	0.4273	0.101*
C38	0.5098 (3)	0.948 (2)	0.5179 (5)	0.077 (3)
H38	0.5325	0.9678	0.5142	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0723 (6)	0.0920 (7)	0.0466 (5)	0.0006 (6)	0.0315 (5)	0.0050 (6)
Br2	0.0428 (5)	0.0592 (5)	0.1048 (7)	−0.0068 (5)	0.0294 (5)	−0.0054 (6)
Br3	0.0519 (5)	0.1045 (8)	0.0825 (6)	−0.0144 (6)	0.0394 (5)	−0.0204 (6)
Br4	0.1052 (7)	0.0843 (6)	0.0493 (5)	−0.0112 (6)	0.0452 (5)	−0.0086 (5)
N1	0.036 (4)	0.048 (4)	0.039 (4)	−0.007 (3)	0.014 (3)	−0.005 (3)
N2	0.039 (4)	0.054 (4)	0.042 (4)	−0.009 (3)	0.000 (3)	0.003 (3)
C1	0.038 (5)	0.028 (5)	0.039 (4)	−0.001 (3)	0.017 (4)	−0.005 (3)
C2	0.039 (5)	0.039 (4)	0.044 (5)	0.006 (3)	0.017 (4)	−0.006 (4)
C3	0.036 (5)	0.056 (5)	0.042 (5)	0.003 (4)	0.015 (4)	−0.011 (4)
C4	0.044 (5)	0.055 (5)	0.031 (4)	0.007 (4)	0.012 (4)	0.001 (4)
C5	0.044 (5)	0.047 (5)	0.063 (5)	−0.008 (4)	0.029 (4)	0.000 (4)
C6	0.035 (4)	0.044 (5)	0.042 (4)	0.004 (4)	0.011 (4)	−0.007 (4)
C7	0.029 (4)	0.039 (4)	0.045 (5)	0.000 (4)	0.012 (4)	0.002 (4)
C8	0.029 (4)	0.033 (4)	0.041 (4)	0.002 (3)	0.016 (4)	0.000 (4)
C9	0.033 (4)	0.037 (4)	0.057 (5)	0.005 (3)	0.012 (4)	−0.008 (4)
C10	0.040 (5)	0.035 (4)	0.081 (6)	0.002 (3)	0.029 (5)	−0.001 (4)
C11	0.055 (6)	0.060 (5)	0.080 (7)	0.009 (4)	0.038 (5)	0.013 (5)
C12	0.039 (5)	0.053 (5)	0.041 (4)	0.003 (4)	0.013 (4)	0.007 (4)
C13	0.045 (5)	0.055 (5)	0.032 (4)	−0.004 (4)	0.010 (4)	−0.013 (4)
C14	0.036 (4)	0.042 (4)	0.033 (4)	−0.009 (4)	0.007 (3)	−0.006 (4)
C15	0.054 (5)	0.052 (5)	0.039 (4)	−0.011 (4)	0.018 (4)	−0.002 (4)
C16	0.039 (6)	0.074 (7)	0.068 (6)	0.009 (5)	0.019 (5)	−0.004 (5)
C17	0.050 (6)	0.064 (6)	0.068 (7)	0.013 (5)	−0.004 (5)	−0.004 (5)
C18	0.075 (7)	0.066 (7)	0.032 (5)	−0.012 (5)	0.004 (5)	−0.006 (4)
C19	0.042 (5)	0.054 (5)	0.038 (4)	−0.009 (4)	0.011 (4)	−0.005 (4)
C20	0.045 (5)	0.044 (5)	0.035 (4)	−0.019 (4)	0.012 (4)	−0.001 (4)
C21	0.027 (4)	0.047 (5)	0.032 (4)	−0.005 (3)	0.004 (3)	−0.003 (4)
C22	0.035 (4)	0.063 (5)	0.031 (4)	−0.009 (4)	0.008 (3)	−0.002 (4)
C23	0.039 (5)	0.067 (5)	0.053 (5)	−0.021 (4)	0.015 (4)	−0.017 (5)
C24	0.070 (7)	0.087 (6)	0.038 (5)	−0.037 (5)	0.023 (5)	−0.008 (5)
C25	0.051 (5)	0.073 (6)	0.035 (4)	−0.025 (5)	0.008 (4)	0.001 (4)
C26	0.037 (5)	0.033 (4)	0.047 (5)	−0.013 (4)	0.006 (4)	−0.006 (4)
C27	0.034 (5)	0.041 (5)	0.039 (4)	−0.005 (4)	0.011 (4)	−0.008 (4)
C28	0.039 (4)	0.050 (5)	0.030 (4)	−0.002 (3)	0.006 (4)	−0.006 (3)
C29	0.072 (6)	0.051 (5)	0.052 (5)	−0.015 (4)	0.036 (5)	−0.014 (4)
C30	0.032 (5)	0.063 (5)	0.068 (6)	−0.012 (4)	0.018 (4)	−0.028 (5)
C31	0.046 (5)	0.062 (6)	0.049 (5)	−0.001 (4)	0.011 (4)	−0.012 (5)
C32	0.057 (6)	0.035 (5)	0.058 (5)	0.003 (4)	0.007 (5)	0.008 (4)
C33	0.057 (6)	0.042 (5)	0.049 (5)	0.006 (4)	0.003 (4)	0.009 (4)
C34	0.058 (6)	0.098 (7)	0.060 (6)	−0.003 (6)	0.019 (5)	−0.010 (5)
C35	0.062 (7)	0.112 (9)	0.055 (6)	−0.025 (6)	0.004 (6)	−0.001 (6)
C36	0.072 (8)	0.080 (7)	0.055 (6)	−0.026 (6)	0.001 (6)	0.004 (6)
C37	0.068 (8)	0.114 (9)	0.052 (6)	−0.005 (6)	0.009 (6)	−0.020 (6)
C38	0.057 (6)	0.101 (7)	0.060 (6)	−0.006 (5)	0.014 (5)	−0.004 (6)

Geometric parameters (Å, º) top

Br1—C4	1.903 (7)	C17—C18	1.353 (11)
Br2—C10	1.906 (7)	C17—H17	0.9300
Br3—C23	1.917 (8)	C18—C19	1.404 (10)
Br4—C29	1.925 (8)	C18—H18	0.9300
N1—C1	1.366 (8)	C19—H19	0.9300
N1—C7	1.403 (8)	C20—C25	1.379 (11)
N1—C13	1.461 (7)	C20—C21	1.414 (9)
N2—C20	1.371 (10)	C21—C22	1.398 (9)
N2—C26	1.393 (10)	C21—C27	1.431 (9)
N2—C32	1.458 (9)	C22—C23	1.374 (9)
C1—C6	1.392 (9)	C22—H22	0.9300
C1—C2	1.413 (9)	C23—C24	1.365 (10)
C2—C3	1.390 (10)	C24—C25	1.391 (11)
C2—C8	1.428 (10)	C24—H24	0.9300
C3—C4	1.356 (10)	C25—H25	0.9300
C3—H3	0.9300	C26—C31	1.384 (11)
C4—C5	1.393 (10)	C26—C27	1.413 (10)
C5—C6	1.386 (10)	C27—C28	1.395 (9)
C5—H5	0.9300	C28—C29	1.361 (9)
C6—H6	0.9300	C28—H28	0.9300
C7—C12	1.381 (9)	C29—C30	1.395 (10)
C7—C8	1.402 (9)	C30—C31	1.353 (11)
C8—C9	1.392 (9)	C30—H30	0.9300
C9—C10	1.373 (9)	C31—H31	0.9300
C9—H9	0.9300	C32—C33	1.508 (10)
C10—C11	1.397 (10)	C32—H32A	0.9700
C11—C12	1.356 (10)	C32—H32B	0.9700
C11—H11	0.9300	C33—C34	1.370 (11)
C12—H12	0.9300	C33—C38	1.382 (11)
C13—C14	1.505 (9)	C34—C35	1.372 (12)
C13—H13A	0.9700	C34—H34	0.9300
C13—H13B	0.9700	C35—C36	1.370 (13)
C14—C19	1.372 (10)	C35—H35	0.9300
C14—C15	1.377 (9)	C36—C37	1.367 (11)
C15—C16	1.388 (11)	C36—H36	0.9300
C15—H15	0.9300	C37—C38	1.378 (12)
C16—C17	1.345 (12)	C37—H37	0.9300
C16—H16	0.9300	C38—H38	0.9300

C1—N1—C7	108.2 (6)	C14—C19—C18	119.9 (8)
C1—N1—C13	127.1 (6)	C14—C19—H19	120.0
C7—N1—C13	123.9 (6)	C18—C19—H19	120.0
C20—N2—C26	108.7 (6)	N2—C20—C25	130.4 (8)
C20—N2—C32	125.3 (7)	N2—C20—C21	109.0 (6)
C26—N2—C32	125.8 (7)	C25—C20—C21	120.6 (8)
N1—C1—C6	129.3 (7)	C22—C21—C20	120.0 (7)
N1—C1—C2	109.6 (6)	C22—C21—C27	132.9 (7)
C6—C1—C2	121.1 (7)	C20—C21—C27	107.0 (6)
C3—C2—C1	119.2 (7)	C23—C22—C21	117.6 (7)
C3—C2—C8	134.5 (7)	C23—C22—H22	121.2
C1—C2—C8	106.3 (6)	C21—C22—H22	121.2
C4—C3—C2	119.1 (7)	C24—C23—C22	122.8 (7)
C4—C3—H3	120.4	C24—C23—Br3	118.6 (6)
C2—C3—H3	120.4	C22—C23—Br3	118.6 (6)
C3—C4—C5	122.3 (7)	C23—C24—C25	120.5 (7)
C3—C4—Br1	120.7 (6)	C23—C24—H24	119.7
C5—C4—Br1	117.0 (6)	C25—C24—H24	119.7
C6—C5—C4	120.0 (7)	C20—C25—C24	118.5 (8)
C6—C5—H5	120.0	C20—C25—H25	120.8
C4—C5—H5	120.0	C24—C25—H25	120.8
C5—C6—C1	118.3 (7)	C31—C26—N2	130.3 (7)
C5—C6—H6	120.9	C31—C26—C27	120.9 (7)
C1—C6—H6	120.9	N2—C26—C27	108.7 (7)
C12—C7—C8	122.2 (7)	C28—C27—C26	119.5 (7)
C12—C7—N1	129.4 (7)	C28—C27—C21	134.0 (7)
C8—C7—N1	108.4 (6)	C26—C27—C21	106.5 (6)
C9—C8—C7	119.0 (7)	C29—C28—C27	117.3 (7)
C9—C8—C2	133.5 (7)	C29—C28—H28	121.3
C7—C8—C2	107.4 (6)	C27—C28—H28	121.3
C10—C9—C8	118.1 (7)	C28—C29—C30	123.4 (7)
C10—C9—H9	120.9	C28—C29—Br4	117.2 (6)
C8—C9—H9	120.9	C30—C29—Br4	119.4 (6)
C9—C10—C11	121.8 (7)	C31—C30—C29	119.4 (8)
C9—C10—Br2	119.0 (6)	C31—C30—H30	120.3
C11—C10—Br2	119.1 (6)	C29—C30—H30	120.3
C12—C11—C10	120.7 (8)	C30—C31—C26	119.3 (7)
C12—C11—H11	119.7	C30—C31—H31	120.3
C10—C11—H11	119.7	C26—C31—H31	120.3
C11—C12—C7	118.1 (7)	N2—C32—C33	112.9 (5)
C11—C12—H12	120.9	N2—C32—H32A	109.0
C7—C12—H12	120.9	C33—C32—H32A	109.0
N1—C13—C14	115.3 (5)	N2—C32—H32B	109.0
N1—C13—H13A	108.5	C33—C32—H32B	109.0
C14—C13—H13A	108.5	H32A—C32—H32B	107.8
N1—C13—H13B	108.5	C34—C33—C38	117.4 (8)
C14—C13—H13B	108.5	C34—C33—C32	122.1 (8)
H13A—C13—H13B	107.5	C38—C33—C32	120.5 (8)
C19—C14—C15	119.0 (7)	C33—C34—C35	121.7 (9)
C19—C14—C13	120.4 (7)	C33—C34—H34	119.1
C15—C14—C13	120.6 (6)	C35—C34—H34	119.1
C14—C15—C16	120.6 (7)	C36—C35—C34	119.6 (10)
C14—C15—H15	119.7	C36—C35—H35	120.2
C16—C15—H15	119.7	C34—C35—H35	120.2
C17—C16—C15	119.4 (8)	C37—C36—C35	120.4 (10)
C17—C16—H16	120.3	C37—C36—H36	119.8
C15—C16—H16	120.3	C35—C36—H36	119.8
C16—C17—C18	121.8 (9)	C36—C37—C38	118.9 (9)
C16—C17—H17	119.1	C36—C37—H37	120.6
C18—C17—H17	119.1	C38—C37—H37	120.6
C17—C18—C19	119.3 (8)	C37—C38—C33	121.9 (9)
C17—C18—H18	120.4	C37—C38—H38	119.0
C19—C18—H18	120.4	C33—C38—H38	119.0

C7—N1—C1—C6	−178.1 (7)	C26—N2—C20—C25	179.9 (7)
C13—N1—C1—C6	−8.1 (12)	C32—N2—C20—C25	4.1 (12)
C7—N1—C1—C2	1.1 (8)	C26—N2—C20—C21	0.0 (8)
C13—N1—C1—C2	171.1 (6)	C32—N2—C20—C21	−175.8 (6)
N1—C1—C2—C3	−179.2 (6)	N2—C20—C21—C22	−178.1 (6)
C6—C1—C2—C3	0.1 (10)	C25—C20—C21—C22	2.0 (10)
N1—C1—C2—C8	0.5 (8)	N2—C20—C21—C27	−0.9 (8)
C6—C1—C2—C8	179.8 (6)	C25—C20—C21—C27	179.2 (6)
C1—C2—C3—C4	0.9 (10)	C20—C21—C22—C23	−1.2 (10)
C8—C2—C3—C4	−178.6 (8)	C27—C21—C22—C23	−177.6 (7)
C2—C3—C4—C5	−1.6 (11)	C21—C22—C23—C24	0.3 (11)
C2—C3—C4—Br1	178.3 (5)	C21—C22—C23—Br3	−179.1 (5)
C3—C4—C5—C6	1.2 (11)	C22—C23—C24—C25	−0.2 (11)
Br1—C4—C5—C6	−178.7 (5)	Br3—C23—C24—C25	179.3 (6)
C4—C5—C6—C1	−0.1 (10)	N2—C20—C25—C24	178.4 (7)
N1—C1—C6—C5	178.6 (7)	C21—C20—C25—C24	−1.8 (11)
C2—C1—C6—C5	−0.5 (10)	C23—C24—C25—C20	0.9 (11)
C1—N1—C7—C12	177.9 (7)	C20—N2—C26—C31	178.6 (8)
C13—N1—C7—C12	7.4 (12)	C32—N2—C26—C31	−5.6 (12)
C1—N1—C7—C8	−2.3 (8)	C20—N2—C26—C27	0.9 (8)
C13—N1—C7—C8	−172.7 (6)	C32—N2—C26—C27	176.7 (6)
C12—C7—C8—C9	−1.0 (10)	C31—C26—C27—C28	1.2 (10)
N1—C7—C8—C9	179.1 (6)	N2—C26—C27—C28	179.2 (6)
C12—C7—C8—C2	−177.6 (7)	C31—C26—C27—C21	−179.4 (6)
N1—C7—C8—C2	2.5 (8)	N2—C26—C27—C21	−1.4 (8)
C3—C2—C8—C9	1.8 (14)	C22—C21—C27—C28	−2.6 (13)
C1—C2—C8—C9	−177.7 (7)	C20—C21—C27—C28	−179.3 (7)
C3—C2—C8—C7	177.7 (8)	C22—C21—C27—C26	178.1 (7)
C1—C2—C8—C7	−1.9 (8)	C20—C21—C27—C26	1.4 (8)
C7—C8—C9—C10	0.0 (10)	C26—C27—C28—C29	−2.5 (10)
C2—C8—C9—C10	175.5 (7)	C21—C27—C28—C29	178.3 (7)
C8—C9—C10—C11	0.1 (10)	C27—C28—C29—C30	3.4 (11)
C8—C9—C10—Br2	−178.3 (5)	C27—C28—C29—Br4	−179.2 (5)
C9—C10—C11—C12	0.7 (11)	C28—C29—C30—C31	−2.8 (11)
Br2—C10—C11—C12	179.2 (5)	Br4—C29—C30—C31	179.8 (6)
C10—C11—C12—C7	−1.6 (11)	C29—C30—C31—C26	1.3 (11)
C8—C7—C12—C11	1.8 (11)	N2—C26—C31—C30	−178.1 (7)
N1—C7—C12—C11	−178.3 (7)	C27—C26—C31—C30	−0.6 (11)
C1—N1—C13—C14	107.4 (8)	C20—N2—C32—C33	90.7 (9)
C7—N1—C13—C14	−84.0 (8)	C26—N2—C32—C33	−84.5 (9)
N1—C13—C14—C19	118.0 (7)	N2—C32—C33—C34	99.7 (9)
N1—C13—C14—C15	−63.6 (8)	N2—C32—C33—C38	−79.8 (10)
C19—C14—C15—C16	−1.4 (10)	C38—C33—C34—C35	0.8 (13)
C13—C14—C15—C16	−179.8 (7)	C32—C33—C34—C35	−178.7 (8)
C14—C15—C16—C17	2.3 (12)	C33—C34—C35—C36	−0.9 (15)
C15—C16—C17—C18	−1.8 (14)	C34—C35—C36—C37	0.9 (15)
C16—C17—C18—C19	0.5 (14)	C35—C36—C37—C38	−0.8 (15)
C15—C14—C19—C18	0.0 (10)	C36—C37—C38—C33	0.7 (15)
C13—C14—C19—C18	178.4 (6)	C34—C33—C38—C37	−0.8 (13)
C17—C18—C19—C14	0.5 (12)	C32—C33—C38—C37	178.8 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Br3ⁱ	0.93	3.00	3.800 (4)	146
C12—H12···Br1ⁱⁱ	0.93	3.01	3.724 (4)	135
C25—H25···Br4ⁱⁱⁱ	0.93	2.97	3.852 (4)	158

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1, z−1/2; (iii) x, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃Br₂N
M_r	415.12
Crystal system, space group	Monoclinic, Cc
Temperature (K)	294
a, b, c (Å)	39.113 (6), 4.5063 (7), 20.469 (3)
β (°)	116.449 (2)
V (Å³)	3230.1 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.01
Crystal size (mm)	0.24 × 0.18 × 0.14

Data collection
Diffractometer	CCD area detector diffractometer
Absorption correction	Multi-scan SADABS (Bruker, 1997)
T_min, T_max	0.310, 0.496
No. of measured, independent and observed [I > 2σ(I)] reflections	8574, 5698, 3115
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.095, 0.94
No. of reflections	5698
No. of parameters	397
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.40
Absolute structure	Flack (1983), 2371 Friedel pairs.
Absolute structure parameter	0.010 (11)

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Br3ⁱ	0.93	3.00	3.800 (4)	146
C12—H12···Br1ⁱⁱ	0.93	3.01	3.724 (4)	135
C25—H25···Br4ⁱⁱⁱ	0.93	2.97	3.852 (4)	158

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1, z−1/2; (iii) x, −y+2, z−1/2.

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