Crystal structure of (E)-1,2-bis­(6-bromo-9-hexyl-9H-carbazol-3-yl)ethene

In the title compound, the two carbazole groups are nearly coplanar, making a dihedral angle of 16.90 (5)°, and are bridged by vinyl. The crystal structure features π–π and C—H...π inter­actions and C—H...Br short contacts.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.106
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level A
SYMOP01_ALERT_1_A  Wrong symmetry operator for _geom_hbond_site_symmetry_A
            Please use the correct form as defined by the CIF
            dictionary.
PLAT707_ALERT_1_A D...A   Calc  3.9062(19), Rep    2.790(3), Dev..     587.47 Sigma
              C9       -BR1             1.555   2.576 ........     #   87 Check
PLAT707_ALERT_1_A D...A   Calc    3.921(2), Rep    2.790(3), Dev..     565.50 Sigma
              C12      -BR1             1.555   2.576 ........     #   87 Check
PLAT707_ALERT_1_A D...A   Calc    3.932(2), Rep    2.790(3), Dev..     571.00 Sigma
              C11      -BR2             1.555   2.667 ........     #   87 Check

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.768
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....     Please Do !
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9       ..BR1              3.04 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12      ..BR1              3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11      ..BR2              3.03 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14      ..BR2              2.94 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         12 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT728_ALERT_1_G D-H..A  Calc      157.00, Rep      150.00 Dev...       7.00 Degree
              C9      -H9      -BR1        1.555  1.555  2.576     #  156 Check
PLAT728_ALERT_1_G D-H..A  Calc      172.00, Rep      158.00 Dev...      14.00 Degree
              C12     -H12     -BR1        1.555  1.555  2.576     #  156 Check
PLAT728_ALERT_1_G D-H..A  Calc      163.00, Rep      154.00 Dev...       9.00 Degree
              C11     -H11     -BR2        1.555  1.555  2.667     #  156 Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2017 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        115 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   4 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2005).

(E)-1,2-Bis(6-bromo-9-hexyl-9H-carbazol-3-yl)ethene

Crystal data

C38H40Br2N2	Z = 2
Mr = 684.54	F(000) = 704
Triclinic, P1	Dx = 1.446 Mg m^−3
a = 8.5553 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4379 (16) Å	Cell parameters from 7151 reflections
c = 17.333 (2) Å	θ = 2.5–27.4°
α = 101.247 (2)°	µ = 2.61 mm^−1
β = 98.392 (1)°	T = 296 K
γ = 104.990 (2)°	Block, pale yellow
V = 1572.0 (4) Å^3	0.50 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer	7063 independent reflections
Radiation source: fine-focus sealed tube	5602 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −11→11
Tmin = 0.477, Tmax = 0.659	k = −14→14
18097 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 0.77	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
7063 reflections	(Δ/σ)max = 0.033
381 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.07518 (3)	1.08100 (2)	0.368357 (13)	0.03674 (9)
Br2	0.48276 (3)	0.47768 (2)	1.151520 (13)	0.03649 (9)
N1	0.4919 (2)	0.74884 (16)	0.43613 (10)	0.0292 (4)
N2	−0.0392 (2)	0.70603 (16)	1.03984 (10)	0.0290 (4)
C1	1.1045 (3)	0.4685 (2)	0.39475 (17)	0.0485 (6)
H1A	1.1716	0.5189	0.4456	0.073*
H1B	1.1708	0.4298	0.3643	0.073*
H1C	1.0153	0.4052	0.4035	0.073*
C2	1.0354 (3)	0.5495 (2)	0.34896 (14)	0.0357 (5)
H2A	0.9748	0.4989	0.2961	0.043*
H2B	1.1265	0.6142	0.3415	0.043*
C3	0.9216 (3)	0.6105 (2)	0.39002 (13)	0.0316 (5)
H3A	0.9814	0.6600	0.4432	0.038*
H3B	0.8292	0.5459	0.3966	0.038*
C4	0.8552 (3)	0.6937 (2)	0.34368 (13)	0.0311 (4)
H4A	0.7862	0.6423	0.2927	0.037*
H4B	0.9476	0.7526	0.3322	0.037*
C5	0.7551 (3)	0.7660 (2)	0.38762 (13)	0.0320 (5)
H5A	0.7431	0.8322	0.3619	0.038*
H5B	0.8151	0.8044	0.4426	0.038*
C6	0.5841 (3)	0.68408 (19)	0.38851 (13)	0.0319 (5)
H6A	0.5210	0.6516	0.3337	0.038*
H6B	0.5961	0.6136	0.4096	0.038*
C7	0.4684 (2)	0.73873 (18)	0.51204 (12)	0.0260 (4)
C8	0.3640 (2)	0.80997 (17)	0.53622 (12)	0.0240 (4)
C9	0.3180 (2)	0.81224 (17)	0.61012 (11)	0.0264 (4)
H9	0.2492	0.8592	0.6261	0.032*
C10	0.3754 (2)	0.74392 (18)	0.66009 (12)	0.0274 (4)
C11	0.3229 (3)	0.7348 (2)	0.73609 (12)	0.0298 (4)
H11	0.3830	0.7018	0.7707	0.036*
C12	0.1974 (3)	0.76918 (19)	0.76010 (12)	0.0290 (4)
H12	0.1424	0.8068	0.7267	0.035*
C13	0.1359 (2)	0.75442 (19)	0.83351 (12)	0.0283 (4)
C14	0.2124 (2)	0.70651 (17)	0.89176 (11)	0.0267 (4)
H14	0.3077	0.6841	0.8855	0.032*
C15	0.1458 (2)	0.69252 (18)	0.95890 (12)	0.0265 (4)
C16	0.0028 (2)	0.72944 (19)	0.96916 (12)	0.0278 (4)
C17	−0.1801 (2)	0.7281 (2)	1.07101 (13)	0.0314 (5)
H17A	−0.2301	0.6583	1.0923	0.038*
H17B	−0.2617	0.7320	1.0272	0.038*
C18	−0.1347 (3)	0.8482 (2)	1.13693 (14)	0.0361 (5)
H18A	−0.0536	0.8443	1.1810	0.043*
H18B	−0.0844	0.9182	1.1158	0.043*
C19	−0.2842 (3)	0.8703 (2)	1.16877 (13)	0.0344 (5)
H19A	−0.3470	0.7934	1.1792	0.041*
H19B	−0.2453	0.9325	1.2196	0.041*
C20	−0.3993 (3)	0.9134 (2)	1.11272 (12)	0.0306 (4)
H20A	−0.3361	0.9880	1.0998	0.037*
H20B	−0.4442	0.8492	1.0630	0.037*
C21	−0.5411 (3)	0.9413 (2)	1.14864 (13)	0.0323 (5)
H21A	−0.4966	0.9951	1.2023	0.039*
H21B	−0.6138	0.8638	1.1537	0.039*
C22	−0.6416 (3)	1.0029 (2)	1.10040 (16)	0.0448 (6)
H22A	−0.5721	1.0817	1.0972	0.067*
H22B	−0.7299	1.0161	1.1261	0.067*
H22C	−0.6870	0.9502	1.0472	0.067*
C23	0.3243 (2)	0.86664 (18)	0.47177 (11)	0.0241 (4)
C24	0.2259 (2)	0.94360 (18)	0.45978 (12)	0.0244 (4)
H24	0.1709	0.9708	0.4989	0.029*
C25	0.2127 (2)	0.97824 (19)	0.38768 (12)	0.0276 (4)
C26	0.2924 (3)	0.9391 (2)	0.32750 (13)	0.0317 (5)
H26	0.2804	0.9650	0.2799	0.038*
C27	0.3894 (3)	0.8616 (2)	0.33856 (12)	0.0314 (5)
H27	0.4425	0.8340	0.2987	0.038*
C28	0.4054 (2)	0.82602 (19)	0.41109 (12)	0.0268 (4)
C29	0.0727 (2)	0.65426 (19)	1.07554 (12)	0.0275 (4)
C30	0.0789 (3)	0.6144 (2)	1.14621 (13)	0.0319 (5)
H30	0.0020	0.6224	1.1781	0.038*
C31	0.2025 (3)	0.5627 (2)	1.16787 (13)	0.0326 (5)
H31	0.2091	0.5345	1.2147	0.039*
C32	0.3170 (3)	0.55263 (19)	1.11963 (12)	0.0288 (4)
C33	0.3143 (2)	0.59188 (18)	1.04918 (11)	0.0260 (4)
H33	0.3921	0.5835	1.0179	0.031*
C34	0.1905 (2)	0.64437 (18)	1.02687 (12)	0.0250 (4)
C35	−0.0731 (3)	0.7797 (2)	0.91302 (14)	0.0330 (5)
H35	−0.1658	0.8052	0.9203	0.040*
C36	−0.0061 (3)	0.7904 (2)	0.84590 (13)	0.0315 (4)
H36	−0.0567	0.8226	0.8073	0.038*
C37	0.4842 (3)	0.6770 (2)	0.63531 (13)	0.0309 (4)
H37	0.5258	0.6340	0.6696	0.037*
C38	0.5315 (3)	0.6729 (2)	0.56168 (13)	0.0315 (5)
H38	0.6027	0.6278	0.5463	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.03362 (13)	0.04857 (15)	0.03772 (14)	0.02071 (10)	0.00922 (10)	0.01996 (10)
Br2	0.03889 (14)	0.04713 (15)	0.03280 (14)	0.02262 (11)	0.01095 (10)	0.01533 (10)
N1	0.0315 (9)	0.0318 (9)	0.0308 (9)	0.0152 (7)	0.0158 (8)	0.0076 (7)
N2	0.0274 (9)	0.0350 (9)	0.0298 (9)	0.0131 (7)	0.0133 (7)	0.0092 (7)
C1	0.0410 (14)	0.0496 (15)	0.0563 (16)	0.0221 (12)	0.0036 (12)	0.0093 (12)
C2	0.0280 (10)	0.0365 (12)	0.0435 (13)	0.0109 (9)	0.0136 (10)	0.0052 (10)
C3	0.0285 (10)	0.0356 (11)	0.0324 (11)	0.0096 (9)	0.0136 (9)	0.0063 (9)
C4	0.0292 (10)	0.0352 (11)	0.0302 (11)	0.0096 (9)	0.0123 (9)	0.0063 (8)
C5	0.0341 (11)	0.0317 (11)	0.0347 (11)	0.0126 (9)	0.0154 (9)	0.0081 (8)
C6	0.0311 (11)	0.0309 (11)	0.0367 (11)	0.0143 (8)	0.0144 (9)	0.0028 (9)
C7	0.0254 (9)	0.0256 (10)	0.0281 (10)	0.0076 (8)	0.0099 (8)	0.0058 (8)
C8	0.0217 (9)	0.0237 (9)	0.0269 (10)	0.0070 (7)	0.0067 (8)	0.0051 (7)
C9	0.0257 (10)	0.0277 (10)	0.0290 (11)	0.0105 (8)	0.0109 (8)	0.0069 (8)
C10	0.0267 (10)	0.0276 (10)	0.0307 (11)	0.0097 (8)	0.0099 (8)	0.0084 (8)
C11	0.0321 (11)	0.0343 (11)	0.0289 (11)	0.0134 (9)	0.0090 (9)	0.0147 (8)
C12	0.0328 (11)	0.0314 (11)	0.0277 (11)	0.0133 (9)	0.0091 (9)	0.0114 (8)
C13	0.0304 (10)	0.0278 (10)	0.0295 (11)	0.0104 (8)	0.0110 (9)	0.0077 (8)
C14	0.0271 (10)	0.0288 (11)	0.0279 (11)	0.0116 (8)	0.0111 (8)	0.0065 (8)
C15	0.0267 (10)	0.0265 (10)	0.0268 (10)	0.0092 (8)	0.0088 (8)	0.0034 (8)
C16	0.0272 (10)	0.0284 (10)	0.0297 (10)	0.0101 (8)	0.0109 (8)	0.0053 (8)
C17	0.0252 (10)	0.0363 (11)	0.0356 (11)	0.0128 (8)	0.0137 (9)	0.0050 (9)
C18	0.0299 (11)	0.0395 (12)	0.0380 (12)	0.0144 (9)	0.0099 (9)	0.0002 (9)
C19	0.0351 (11)	0.0414 (12)	0.0303 (11)	0.0193 (10)	0.0107 (9)	0.0034 (9)
C20	0.0326 (11)	0.0320 (11)	0.0293 (11)	0.0111 (9)	0.0130 (9)	0.0052 (8)
C21	0.0311 (10)	0.0329 (11)	0.0344 (11)	0.0113 (8)	0.0129 (9)	0.0046 (8)
C22	0.0398 (13)	0.0455 (14)	0.0540 (15)	0.0190 (11)	0.0112 (11)	0.0134 (11)
C23	0.0242 (9)	0.0247 (9)	0.0227 (9)	0.0057 (7)	0.0069 (8)	0.0044 (7)
C24	0.0222 (9)	0.0257 (10)	0.0259 (10)	0.0076 (7)	0.0067 (8)	0.0054 (7)
C25	0.0242 (9)	0.0309 (10)	0.0287 (10)	0.0080 (8)	0.0068 (8)	0.0088 (8)
C26	0.0321 (11)	0.0392 (12)	0.0249 (10)	0.0085 (9)	0.0083 (9)	0.0114 (8)
C27	0.0328 (11)	0.0363 (11)	0.0261 (10)	0.0099 (9)	0.0125 (9)	0.0059 (8)
C28	0.0260 (10)	0.0278 (10)	0.0268 (10)	0.0079 (8)	0.0100 (8)	0.0038 (8)
C29	0.0269 (10)	0.0272 (10)	0.0282 (10)	0.0084 (8)	0.0103 (8)	0.0024 (8)
C30	0.0338 (11)	0.0364 (11)	0.0280 (11)	0.0108 (9)	0.0154 (9)	0.0064 (8)
C31	0.0386 (12)	0.0363 (11)	0.0262 (10)	0.0124 (9)	0.0120 (9)	0.0096 (8)
C32	0.0310 (10)	0.0302 (11)	0.0265 (10)	0.0116 (8)	0.0090 (8)	0.0042 (8)
C33	0.0274 (10)	0.0272 (10)	0.0244 (10)	0.0096 (8)	0.0094 (8)	0.0036 (7)
C34	0.0261 (10)	0.0248 (10)	0.0239 (10)	0.0073 (8)	0.0082 (8)	0.0032 (7)
C35	0.0298 (11)	0.0345 (11)	0.0415 (12)	0.0163 (9)	0.0138 (9)	0.0112 (9)
C36	0.0315 (11)	0.0341 (11)	0.0349 (11)	0.0155 (9)	0.0098 (9)	0.0126 (9)
C37	0.0307 (10)	0.0323 (11)	0.0360 (12)	0.0148 (8)	0.0099 (9)	0.0133 (9)
C38	0.0309 (10)	0.0324 (11)	0.0393 (12)	0.0182 (9)	0.0140 (9)	0.0106 (9)

Geometric parameters (Å, º)

Br1—C25	1.906 (2)	C16—C35	1.388 (3)
Br2—C32	1.907 (2)	C17—C18	1.525 (3)
N1—C7	1.382 (3)	C17—H17A	0.9700
N1—C28	1.382 (3)	C17—H17B	0.9700
N1—C6	1.451 (2)	C18—C19	1.524 (3)
N2—C16	1.382 (3)	C18—H18A	0.9700
N2—C29	1.383 (3)	C18—H18B	0.9700
N2—C17	1.450 (2)	C19—C20	1.522 (3)
C1—C2	1.507 (3)	C19—H19A	0.9700
C1—H1A	0.9600	C19—H19B	0.9700
C1—H1B	0.9600	C20—C21	1.518 (3)
C1—H1C	0.9600	C20—H20A	0.9700
C2—C3	1.517 (3)	C20—H20B	0.9700
C2—H2A	0.9700	C21—C22	1.506 (3)
C2—H2B	0.9700	C21—H21A	0.9700
C3—C4	1.523 (3)	C21—H21B	0.9700
C3—H3A	0.9700	C22—H22A	0.9600
C3—H3B	0.9700	C22—H22B	0.9600
C4—C5	1.519 (3)	C22—H22C	0.9600
C4—H4A	0.9700	C23—C24	1.389 (3)
C4—H4B	0.9700	C23—C28	1.412 (3)
C5—C6	1.524 (3)	C24—C25	1.381 (3)
C5—H5A	0.9700	C24—H24	0.9300
C5—H5B	0.9700	C25—C26	1.392 (3)
C6—H6A	0.9700	C26—C27	1.383 (3)
C6—H6B	0.9700	C26—H26	0.9300
C7—C38	1.388 (3)	C27—C28	1.394 (3)
C7—C8	1.411 (3)	C27—H27	0.9300
C8—C9	1.391 (3)	C29—C30	1.386 (3)
C8—C23	1.438 (3)	C29—C34	1.417 (3)
C9—C10	1.393 (3)	C30—C31	1.380 (3)
C9—H9	0.9300	C30—H30	0.9300
C10—C37	1.412 (3)	C31—C32	1.390 (3)
C10—C11	1.466 (3)	C31—H31	0.9300
C11—C12	1.329 (3)	C32—C33	1.380 (3)
C11—H11	0.9300	C33—C34	1.390 (3)
C12—C13	1.469 (3)	C33—H33	0.9300
C12—H12	0.9300	C35—C36	1.382 (3)
C13—C14	1.399 (3)	C35—H35	0.9300
C13—C36	1.411 (3)	C36—H36	0.9300
C14—C15	1.387 (3)	C37—C38	1.390 (3)
C14—H14	0.9300	C37—H37	0.9300
C15—C16	1.417 (3)	C38—H38	0.9300
C15—C34	1.438 (3)
C7—N1—C28	108.54 (16)	C19—C18—C17	112.46 (18)
C7—N1—C6	125.99 (18)	C19—C18—H18A	109.1
C28—N1—C6	125.38 (18)	C17—C18—H18A	109.1
C16—N2—C29	108.88 (16)	C19—C18—H18B	109.1
C16—N2—C17	126.08 (18)	C17—C18—H18B	109.1
C29—N2—C17	125.02 (18)	H18A—C18—H18B	107.8
C2—C1—H1A	109.5	C20—C19—C18	114.68 (18)
C2—C1—H1B	109.5	C20—C19—H19A	108.6
H1A—C1—H1B	109.5	C18—C19—H19A	108.6
C2—C1—H1C	109.5	C20—C19—H19B	108.6
H1A—C1—H1C	109.5	C18—C19—H19B	108.6
H1B—C1—H1C	109.5	H19A—C19—H19B	107.6
C1—C2—C3	113.9 (2)	C21—C20—C19	112.96 (17)
C1—C2—H2A	108.8	C21—C20—H20A	109.0
C3—C2—H2A	108.8	C19—C20—H20A	109.0
C1—C2—H2B	108.8	C21—C20—H20B	109.0
C3—C2—H2B	108.8	C19—C20—H20B	109.0
H2A—C2—H2B	107.7	H20A—C20—H20B	107.8
C2—C3—C4	113.19 (18)	C20—C21—C22	114.16 (19)
C2—C3—H3A	108.9	C20—C21—H21A	108.7
C4—C3—H3A	108.9	C22—C21—H21A	108.7
C2—C3—H3B	108.9	C20—C21—H21B	108.7
C4—C3—H3B	108.9	C22—C21—H21B	108.7
H3A—C3—H3B	107.8	H21A—C21—H21B	107.6
C3—C4—C5	114.11 (17)	C21—C22—H22A	109.5
C3—C4—H4A	108.7	C21—C22—H22B	109.5
C5—C4—H4A	108.7	H22A—C22—H22B	109.5
C3—C4—H4B	108.7	C21—C22—H22C	109.5
C5—C4—H4B	108.7	H22A—C22—H22C	109.5
H4A—C4—H4B	107.6	H22B—C22—H22C	109.5
C4—C5—C6	112.79 (17)	C24—C23—C28	119.99 (18)
C4—C5—H5A	109.0	C24—C23—C8	133.57 (17)
C6—C5—H5A	109.0	C28—C23—C8	106.41 (17)
C4—C5—H5B	109.0	C25—C24—C23	117.61 (17)
C6—C5—H5B	109.0	C25—C24—H24	121.2
H5A—C5—H5B	107.8	C23—C24—H24	121.2
N1—C6—C5	113.69 (17)	C24—C25—C26	122.94 (19)
N1—C6—H6A	108.8	C24—C25—Br1	118.72 (15)
C5—C6—H6A	108.8	C26—C25—Br1	118.33 (16)
N1—C6—H6B	108.8	C27—C26—C25	119.9 (2)
C5—C6—H6B	108.8	C27—C26—H26	120.1
H6A—C6—H6B	107.7	C25—C26—H26	120.1
N1—C7—C38	129.56 (18)	C28—C27—C26	118.18 (18)
N1—C7—C8	109.08 (17)	C28—C27—H27	120.9
C38—C7—C8	121.37 (18)	C26—C27—H27	120.9
C9—C8—C7	120.07 (18)	N1—C28—C27	129.37 (18)
C9—C8—C23	133.19 (18)	N1—C28—C23	109.24 (18)
C7—C8—C23	106.73 (16)	C27—C28—C23	121.38 (19)
C8—C9—C10	119.78 (17)	C30—C29—N2	129.50 (18)
C8—C9—H9	120.1	C30—C29—C34	121.60 (19)
C10—C9—H9	120.1	N2—C29—C34	108.90 (18)
C9—C10—C37	118.72 (18)	C29—C30—C31	118.11 (18)
C9—C10—C11	122.78 (17)	C29—C30—H30	120.9
C37—C10—C11	118.46 (19)	C31—C30—H30	120.9
C12—C11—C10	126.0 (2)	C30—C31—C32	120.0 (2)
C12—C11—H11	117.0	C30—C31—H31	120.0
C10—C11—H11	117.0	C32—C31—H31	120.0
C11—C12—C13	127.3 (2)	C33—C32—C31	123.2 (2)
C11—C12—H12	116.4	C33—C32—Br2	118.65 (15)
C13—C12—H12	116.4	C31—C32—Br2	118.17 (16)
C14—C13—C36	118.61 (18)	C32—C33—C34	117.33 (18)
C14—C13—C12	122.78 (18)	C32—C33—H33	121.3
C36—C13—C12	118.61 (19)	C34—C33—H33	121.3
C15—C14—C13	119.81 (17)	C33—C34—C29	119.81 (19)
C15—C14—H14	120.1	C33—C34—C15	133.55 (18)
C13—C14—H14	120.1	C29—C34—C15	106.61 (17)
C14—C15—C16	119.93 (19)	C16—C35—C36	117.65 (19)
C14—C15—C34	133.42 (18)	C16—C35—H35	121.2
C16—C15—C34	106.66 (17)	C36—C35—H35	121.2
N2—C16—C35	129.78 (18)	C35—C36—C13	122.7 (2)
N2—C16—C15	108.96 (18)	C35—C36—H36	118.6
C35—C16—C15	121.26 (18)	C13—C36—H36	118.6
N2—C17—C18	113.14 (17)	C38—C37—C10	122.59 (19)
N2—C17—H17A	109.0	C38—C37—H37	118.7
C18—C17—H17A	109.0	C10—C37—H37	118.7
N2—C17—H17B	109.0	C7—C38—C37	117.42 (18)
C18—C17—H17B	109.0	C7—C38—H38	121.3
H17A—C17—H17B	107.8	C37—C38—H38	121.3

Hydrogen-bond geometry (Å, º)

Cg6 is the centroid of the C29–C34 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Br1^i	0.93	3.04	3.9062 (19)	157
C12—H12···Br1^i	0.93	3.00	3.921 (2)	172
C11—H11···Br2^ii	0.93	3.03	3.932 (2)	163
C14—H14···Br2^ii	0.93	2.94	3.821 (2)	159
C21—H21B···Cg6^iii	0.93	2.89	3.791 (3)	154

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

Analysis of Short Ring-Interactions with Cg-Cg (Å, °)

Cg(I)	Cg(J) [ ARU(J)]	Cg-Cg	α	CgI_Perp	CgJ_Perp
Cg(1)	Cg(1) [2656.01]	4.3365	0	-3.5042	-3.5042
Cg(1)	Cg(3) [2656.01]	5.4195	1.424	-3.5070	-3.5193
Cg(1)	Cg(5) [2656.01]	3.6898	1.126	-3.5290	-3.5284
Cg(2)	Cg(2) [2765.01]	4.0065	0	3.5166	3.5166
Cg(2)	Cg(4) [2765.01]	5.2650	0.997	3.5672	3.5002
Cg(2)	Cg(6) [2765.01]	3.5000	1.275	3.4956	3.4909
Cg(3)	Cg(1) [2656.01]	5.4195	1.424	-3.5193	-3.5070
Cg(3)	Cg(5) [2656.01]	4.0524	1.960	-3.5814	-3.5354
Cg(4)	Cg(2) [2765.01]	5.2650	0.997	3.5002	3.5672
Cg(4)	Cg(6) [2765.01]	4.0191	2.123	3.4465	3.5085
Cg(5)	Cg(1) [2656.01]	3.6898	1.126	-3.5284	-3.5290
Cg(5)	Cg(3) [2656.01]	4.0524	1.960	-3.5354	-3.5814
Cg(5)	Cg(5) [2656.01]	4.2114	0	-3.5109	-3.5109
Cg(5)	Cg(6) [1556.01]	5.4638	16.970	-4.0104	3.0948
Cg(6)	Cg(2) [2765.01]	3.5000	1.275	3.4909	3.4956
Cg(6)	Cg(4) [2765.01]	4.0191	2.123	3.5085	3.4465
Cg(6)	Cg(5) [1554.01]	5.4638	16.970	3.0948	-4.0104
Cg(6)	Cg(6) [2765.01]	4.2119	0	3.5165	3.5165

Cg(I), Cg(J): Plane number I,J (ring number in figure 1); Cg-Cg: Distance between ring Centroids (Ang.); α: Dihedral Angle between Planes I and J (Deg); CgI_Perp: Perpendicular distance of Cg(I) on ring J (Ang.); CgJ_Perp: Perpendicular distance of Cg(J) on ring I (Ang.); [2656.01]: 1-X, -Y, 1-Z; [2765.01] = 2-X, 1-Y, -Z; [1556.01] = X, Y, 1+Z; [1554.01] = X, Y, -1+Z.

The fractional coordinates of single crystal

CgI	x	y	z
Cg1	0.589228	0.201962	0.526550
Cg2	0.925482	0.314678	-0.014062
Cg3	0.576427	0.257533	0.414090
Cg4	0.930362	0.257838	0.097958
Cg5	0.691673	0.097473	0.600602
Cg6	0.804030	0.396628	-0.097550