Crystal structure of 4-bromo-N-[(3,6-di-tert-butyl-9H-carbazol-1-yl)methyl­idene]aniline

In the title compound, C₂₇H₂₉BrN₂, an intra­molecular N—H...N hydrogen bond forms an S(6) ring motif. In the crystal, two mol­ecules are associated into an inversion dimer via a pair of C—H...π inter­actions. The dimers are linked by another pair of C—H...π inter­actions, forming a ribbon along the c-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.034
• wR factor = 0.076
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT352_ALERT_3_C Short  N-H (X0.87,N1.01A)  N3       - H3       .       0.76 Ang.

Author Response: The N3...H3 bond length is 0.76(3) \%A, shorter than the ideal value. As described in pub_section_exptl_refinement, the amino H atom was located in difference Fourier map and freely refined. We tried to refine the amino H atom in the riding model (0.86 \%A); nevertheless, R, wR and GOF in the freely refinement are better than those in the riding model.

PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.818 Check

Author Response: We examined about the cause of this Alert, but could not find it. We consider that the Alert is not so serious problem...

PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Author Response: The completeness of the data collection is 0.999. We consider that the missing reflections dose not affect refinment of the structure.

Alert level G
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        10% Note
PLAT882_ALERT_1_G No Datum for _diffrn_reflns_av_unetI/netI ......     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         21 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: CrystalStructure (Rigaku, 2016).

4-Bromo-N-[(3,6-di-tert-butyl-9H-carbazol-1-yl)methylidene]aniline

Crystal data

C27H29BrN2	F(000) = 960.00
Mr = 461.42	Dx = 1.333 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 9.9949 (5) Å	Cell parameters from 8890 reflections
b = 23.546 (1) Å	θ = 2.3–30.3°
c = 10.2919 (6) Å	µ = 1.80 mm^−1
β = 108.334 (6)°	T = 123 K
V = 2299.2 (2) Å^3	Prism, yellow
Z = 4	0.40 × 0.30 × 0.20 mm

Data collection

Rigaku AFC HyPix-6000 diffractometer	5268 independent reflections
Radiation source: rotating anode X-ray generator, FR-E+	4580 reflections with F^2 > 2.0σ(F^2)
Multi-layer mirror optics monochromator	Rint = 0.025
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 2.3°
ω scans	h = −10→12
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −26→30
Tmin = 0.610, Tmax = 0.696	l = −13→13
19373 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0306P)^2 + 1.3852P] where P = (Fo^2 + 2Fc^2)/3
5268 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3
Primary atom site location: structure-invariant direct methods

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.32389 (2)	−0.22866 (2)	−0.02368 (2)	0.04191 (8)
N2	0.10884 (14)	−0.03518 (6)	0.24791 (14)	0.0214 (3)
N3	0.13607 (14)	0.05539 (6)	0.44000 (14)	0.0194 (3)
C4	−0.00730 (16)	0.05269 (6)	0.37843 (15)	0.0178 (3)
C5	−0.07237 (16)	0.09426 (6)	0.43609 (15)	0.0171 (3)
C6	−0.21856 (16)	0.10061 (7)	0.38848 (16)	0.0190 (3)
H6	−0.2609	0.1292	0.4243	0.023*
C7	−0.30146 (16)	0.06474 (7)	0.28826 (16)	0.0202 (3)
C8	−0.23344 (17)	0.02255 (7)	0.23600 (16)	0.0210 (3)
H8	−0.2887	−0.0021	0.1703	0.025*
C9	−0.08739 (16)	0.01562 (6)	0.27729 (16)	0.0187 (3)
C10	0.16594 (16)	0.09673 (6)	0.54128 (16)	0.0183 (3)
C11	0.03872 (15)	0.12215 (6)	0.54154 (15)	0.0169 (3)
C12	0.03888 (16)	0.16442 (6)	0.63623 (15)	0.0172 (3)
H12	−0.0456	0.1811	0.6359	0.021*
C13	0.16444 (16)	0.18174 (6)	0.73110 (15)	0.0183 (3)
C14	0.29004 (16)	0.15590 (7)	0.72658 (16)	0.0213 (3)
H14	0.3748	0.1675	0.7894	0.026*
C15	0.29330 (16)	0.11409 (7)	0.63310 (17)	0.0216 (3)
H15	0.3781	0.0982	0.6319	0.026*
C16	−0.46276 (17)	0.06969 (7)	0.23445 (18)	0.0249 (4)
C17	−0.5292 (2)	0.01470 (9)	0.2628 (2)	0.0423 (5)
H17A	−0.5002	0.0079	0.3597	0.051*
H17B	−0.4991	−0.0163	0.2182	0.051*
H17C	−0.6300	0.0179	0.2285	0.051*
C18	−0.5096 (2)	0.07977 (9)	0.07942 (19)	0.0351 (4)
H18A	−0.6106	0.0811	0.0447	0.042*
H18B	−0.4758	0.0494	0.0359	0.042*
H18C	−0.4716	0.1152	0.0606	0.042*
C19	−0.51743 (19)	0.11897 (9)	0.2992 (2)	0.0386 (5)
H19A	−0.4766	0.1538	0.2812	0.046*
H19B	−0.4920	0.1132	0.3963	0.046*
H19C	−0.6182	0.1210	0.2610	0.046*
C20	0.16630 (17)	0.22683 (7)	0.83868 (17)	0.0226 (3)
C21A	0.2398 (4)	0.20070 (14)	0.9822 (3)	0.0349 (8)	0.592 (3)
H21A	0.2411	0.2281	1.0517	0.042*	0.592 (3)
H21B	0.3347	0.1903	0.9893	0.042*	0.592 (3)
H21C	0.1890	0.1676	0.9943	0.042*	0.592 (3)
C22A	0.0240 (4)	0.24682 (17)	0.8322 (4)	0.0458 (11)	0.592 (3)
H22A	−0.0202	0.2644	0.7452	0.055*	0.592 (3)
H22B	0.0317	0.2739	0.9040	0.055*	0.592 (3)
H22C	−0.0318	0.2151	0.8434	0.055*	0.592 (3)
C23A	0.2585 (4)	0.27633 (13)	0.8214 (3)	0.0344 (8)	0.592 (3)
H23A	0.2170	0.2935	0.7333	0.041*	0.592 (3)
H23B	0.3509	0.2625	0.8284	0.041*	0.592 (3)
H23C	0.2655	0.3040	0.8917	0.041*	0.592 (3)
C21B	0.0816 (5)	0.2036 (2)	0.9295 (4)	0.0310 (11)	0.408 (3)
H21D	0.1277	0.1705	0.9775	0.037*	0.408 (3)
H21E	−0.0118	0.1937	0.8731	0.037*	0.408 (3)
H21F	0.0762	0.2321	0.9943	0.037*	0.408 (3)
C22B	0.0843 (5)	0.28167 (19)	0.7672 (5)	0.0324 (11)	0.408 (3)
H22D	0.0760	0.3078	0.8359	0.039*	0.408 (3)
H22E	−0.0080	0.2711	0.7094	0.039*	0.408 (3)
H22F	0.1351	0.2994	0.7130	0.039*	0.408 (3)
C23B	0.3089 (4)	0.2460 (2)	0.9280 (5)	0.0346 (12)	0.408 (3)
H23D	0.3601	0.2140	0.9772	0.041*	0.408 (3)
H23E	0.2979	0.2739	0.9917	0.041*	0.408 (3)
H23F	0.3599	0.2622	0.8721	0.041*	0.408 (3)
C24	−0.02473 (16)	−0.02866 (7)	0.21740 (16)	0.0197 (3)
H24	−0.0838	−0.0533	0.1544	0.024*
C25	0.15800 (17)	−0.07912 (7)	0.18052 (16)	0.0207 (3)
C26	0.26499 (17)	−0.11434 (7)	0.25860 (18)	0.0235 (3)
H26	0.3037	−0.1079	0.3521	0.028*
C27	0.31439 (17)	−0.15892 (7)	0.19842 (19)	0.0263 (4)
H27	0.3834	−0.1833	0.2514	0.032*
C28	0.25953 (18)	−0.16661 (7)	0.05853 (19)	0.0263 (4)
C29	0.15945 (19)	−0.13042 (8)	−0.02231 (19)	0.0288 (4)
H29	0.1269	−0.1351	−0.1168	0.035*
C30	0.10778 (18)	−0.08681 (7)	0.03954 (17)	0.0261 (4)
H30	0.0389	−0.0625	−0.0140	0.031*
H3	0.187 (2)	0.0341 (9)	0.426 (2)	0.027 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.03992 (12)	0.03025 (11)	0.05975 (15)	0.00525 (8)	0.02168 (10)	−0.01567 (9)
N2	0.0257 (7)	0.0183 (6)	0.0222 (7)	−0.0004 (5)	0.0103 (6)	−0.0001 (5)
N3	0.0172 (6)	0.0193 (7)	0.0222 (7)	0.0024 (5)	0.0069 (5)	−0.0017 (5)
C4	0.0192 (7)	0.0168 (7)	0.0181 (7)	0.0000 (6)	0.0066 (6)	0.0036 (6)
C5	0.0208 (7)	0.0157 (7)	0.0154 (7)	−0.0007 (6)	0.0065 (6)	0.0015 (6)
C6	0.0196 (7)	0.0182 (7)	0.0194 (8)	0.0025 (6)	0.0065 (6)	0.0007 (6)
C7	0.0185 (8)	0.0211 (8)	0.0198 (8)	0.0005 (6)	0.0045 (6)	0.0009 (6)
C8	0.0229 (8)	0.0183 (7)	0.0202 (8)	−0.0021 (6)	0.0045 (6)	−0.0017 (6)
C9	0.0225 (8)	0.0161 (7)	0.0188 (7)	0.0000 (6)	0.0082 (6)	0.0016 (6)
C10	0.0214 (8)	0.0160 (7)	0.0186 (7)	0.0009 (6)	0.0078 (6)	0.0021 (6)
C11	0.0166 (7)	0.0165 (7)	0.0175 (7)	−0.0006 (6)	0.0053 (6)	0.0035 (6)
C12	0.0163 (7)	0.0166 (7)	0.0193 (7)	0.0007 (6)	0.0063 (6)	0.0020 (6)
C13	0.0200 (7)	0.0178 (7)	0.0178 (7)	−0.0018 (6)	0.0068 (6)	0.0018 (6)
C14	0.0164 (7)	0.0246 (8)	0.0207 (8)	−0.0023 (6)	0.0025 (6)	0.0006 (6)
C15	0.0159 (7)	0.0234 (8)	0.0258 (8)	0.0029 (6)	0.0067 (6)	0.0020 (7)
C16	0.0175 (8)	0.0246 (8)	0.0291 (9)	−0.0008 (6)	0.0023 (7)	−0.0044 (7)
C17	0.0228 (9)	0.0388 (11)	0.0652 (14)	−0.0008 (8)	0.0135 (9)	0.0078 (10)
C18	0.0256 (9)	0.0400 (11)	0.0324 (10)	0.0030 (8)	−0.0013 (8)	−0.0039 (8)
C19	0.0195 (8)	0.0479 (12)	0.0426 (11)	0.0070 (8)	0.0017 (8)	−0.0161 (9)
C20	0.0229 (8)	0.0219 (8)	0.0220 (8)	−0.0047 (6)	0.0058 (6)	−0.0037 (6)
C21A	0.049 (2)	0.0336 (17)	0.0241 (16)	−0.0039 (14)	0.0149 (14)	−0.0042 (13)
C22A	0.0303 (17)	0.047 (2)	0.054 (2)	0.0007 (15)	0.0055 (16)	−0.0364 (19)
C23A	0.0448 (19)	0.0241 (15)	0.0292 (17)	−0.0123 (13)	0.0045 (14)	−0.0049 (13)
C21B	0.039 (3)	0.035 (2)	0.021 (2)	−0.012 (2)	0.0112 (19)	−0.0070 (18)
C22B	0.045 (3)	0.026 (2)	0.026 (2)	0.0088 (19)	0.012 (2)	−0.0038 (18)
C23B	0.021 (2)	0.038 (3)	0.043 (3)	−0.0064 (18)	0.006 (2)	−0.016 (2)
C24	0.0243 (8)	0.0169 (7)	0.0179 (7)	−0.0011 (6)	0.0066 (6)	0.0000 (6)
C25	0.0229 (8)	0.0171 (7)	0.0248 (8)	−0.0020 (6)	0.0114 (7)	−0.0019 (6)
C26	0.0199 (8)	0.0268 (8)	0.0244 (8)	−0.0016 (6)	0.0080 (7)	−0.0007 (7)
C27	0.0202 (8)	0.0238 (8)	0.0368 (10)	0.0024 (6)	0.0117 (7)	0.0028 (7)
C28	0.0258 (8)	0.0194 (8)	0.0389 (10)	−0.0004 (6)	0.0175 (8)	−0.0067 (7)
C29	0.0342 (9)	0.0286 (9)	0.0244 (9)	0.0021 (7)	0.0104 (7)	−0.0050 (7)
C30	0.0306 (9)	0.0232 (8)	0.0244 (9)	0.0054 (7)	0.0084 (7)	0.0016 (7)

Geometric parameters (Å, º)

Br1—C28	1.8992 (16)	C19—H19B	0.9600
N2—C24	1.281 (2)	C19—H19C	0.9600
N2—C25	1.417 (2)	C20—C22A	1.479 (4)
N3—C4	1.374 (2)	C20—C23B	1.502 (4)
N3—C10	1.388 (2)	C20—C23A	1.530 (3)
N3—H3	0.76 (2)	C20—C21B	1.545 (5)
C4—C9	1.401 (2)	C20—C21A	1.555 (4)
C4—C5	1.406 (2)	C20—C22B	1.581 (5)
C5—C6	1.395 (2)	C21A—H21A	0.9600
C5—C11	1.444 (2)	C21A—H21B	0.9600
C6—C7	1.388 (2)	C21A—H21C	0.9600
C6—H6	0.9300	C22A—H22A	0.9600
C7—C8	1.403 (2)	C22A—H22B	0.9600
C7—C16	1.535 (2)	C22A—H22C	0.9600
C8—C9	1.396 (2)	C23A—H23A	0.9600
C8—H8	0.9300	C23A—H23B	0.9600
C9—C24	1.450 (2)	C23A—H23C	0.9600
C10—C15	1.387 (2)	C21B—H21D	0.9600
C10—C11	1.406 (2)	C21B—H21E	0.9600
C11—C12	1.393 (2)	C21B—H21F	0.9600
C12—C13	1.387 (2)	C22B—H22D	0.9600
C12—H12	0.9300	C22B—H22E	0.9600
C13—C14	1.409 (2)	C22B—H22F	0.9600
C13—C20	1.530 (2)	C23B—H23D	0.9600
C14—C15	1.384 (2)	C23B—H23E	0.9600
C14—H14	0.9300	C23B—H23F	0.9600
C15—H15	0.9300	C24—H24	0.9300
C16—C19	1.523 (2)	C25—C30	1.390 (2)
C16—C17	1.525 (3)	C25—C26	1.392 (2)
C16—C18	1.533 (3)	C26—C27	1.386 (2)
C17—H17A	0.9600	C26—H26	0.9300
C17—H17B	0.9600	C27—C28	1.382 (3)
C17—H17C	0.9600	C27—H27	0.9300
C18—H18A	0.9600	C28—C29	1.377 (3)
C18—H18B	0.9600	C29—C30	1.390 (2)
C18—H18C	0.9600	C29—H29	0.9300
C19—H19A	0.9600	C30—H30	0.9300
C24—N2—C25	117.55 (14)	C13—C20—C23A	108.37 (17)
C4—N3—C10	108.99 (13)	C23B—C20—C21B	109.3 (3)
C4—N3—H3	123.0 (15)	C13—C20—C21B	107.9 (2)
C10—N3—H3	127.4 (15)	C22A—C20—C21A	109.2 (2)
N3—C4—C9	129.86 (14)	C13—C20—C21A	107.92 (17)
N3—C4—C5	109.09 (13)	C23A—C20—C21A	106.8 (2)
C9—C4—C5	121.03 (14)	C23B—C20—C22B	107.0 (3)
C6—C5—C4	119.92 (14)	C13—C20—C22B	110.1 (2)
C6—C5—C11	133.48 (14)	C21B—C20—C22B	105.5 (3)
C4—C5—C11	106.59 (13)	C20—C21A—H21A	109.5
C7—C6—C5	120.68 (14)	C20—C21A—H21B	109.5
C7—C6—H6	119.7	H21A—C21A—H21B	109.5
C5—C6—H6	119.7	C20—C21A—H21C	109.5
C6—C7—C8	117.89 (14)	H21A—C21A—H21C	109.5
C6—C7—C16	122.38 (14)	H21B—C21A—H21C	109.5
C8—C7—C16	119.73 (14)	C20—C22A—H22A	109.5
C9—C8—C7	123.55 (15)	C20—C22A—H22B	109.5
C9—C8—H8	118.2	H22A—C22A—H22B	109.5
C7—C8—H8	118.2	C20—C22A—H22C	109.5
C8—C9—C4	116.87 (14)	H22A—C22A—H22C	109.5
C8—C9—C24	120.32 (14)	H22B—C22A—H22C	109.5
C4—C9—C24	122.80 (14)	C20—C23A—H23A	109.5
C15—C10—N3	130.74 (14)	C20—C23A—H23B	109.5
C15—C10—C11	120.66 (14)	H23A—C23A—H23B	109.5
N3—C10—C11	108.59 (13)	C20—C23A—H23C	109.5
C12—C11—C10	120.24 (14)	H23A—C23A—H23C	109.5
C12—C11—C5	133.04 (14)	H23B—C23A—H23C	109.5
C10—C11—C5	106.69 (13)	C20—C21B—H21D	109.5
C13—C12—C11	120.29 (14)	C20—C21B—H21E	109.5
C13—C12—H12	119.9	H21D—C21B—H21E	109.5
C11—C12—H12	119.9	C20—C21B—H21F	109.5
C12—C13—C14	117.91 (14)	H21D—C21B—H21F	109.5
C12—C13—C20	121.06 (14)	H21E—C21B—H21F	109.5
C14—C13—C20	121.03 (14)	C20—C22B—H22D	109.5
C15—C14—C13	123.11 (14)	C20—C22B—H22E	109.5
C15—C14—H14	118.4	H22D—C22B—H22E	109.5
C13—C14—H14	118.4	C20—C22B—H22F	109.5
C14—C15—C10	117.77 (14)	H22D—C22B—H22F	109.5
C14—C15—H15	121.1	H22E—C22B—H22F	109.5
C10—C15—H15	121.1	C20—C23B—H23D	109.5
C19—C16—C17	109.00 (16)	C20—C23B—H23E	109.5
C19—C16—C18	107.66 (15)	H23D—C23B—H23E	109.5
C17—C16—C18	108.79 (15)	C20—C23B—H23F	109.5
C19—C16—C7	112.37 (14)	H23D—C23B—H23F	109.5
C17—C16—C7	109.72 (14)	H23E—C23B—H23F	109.5
C18—C16—C7	109.22 (14)	N2—C24—C9	122.55 (15)
C16—C17—H17A	109.5	N2—C24—H24	118.7
C16—C17—H17B	109.5	C9—C24—H24	118.7
H17A—C17—H17B	109.5	C30—C25—C26	119.00 (15)
C16—C17—H17C	109.5	C30—C25—N2	122.63 (15)
H17A—C17—H17C	109.5	C26—C25—N2	118.32 (14)
H17B—C17—H17C	109.5	C27—C26—C25	120.68 (16)
C16—C18—H18A	109.5	C27—C26—H26	119.7
C16—C18—H18B	109.5	C25—C26—H26	119.7
H18A—C18—H18B	109.5	C28—C27—C26	118.97 (16)
C16—C18—H18C	109.5	C28—C27—H27	120.5
H18A—C18—H18C	109.5	C26—C27—H27	120.5
H18B—C18—H18C	109.5	C29—C28—C27	121.56 (15)
C16—C19—H19A	109.5	C29—C28—Br1	119.37 (14)
C16—C19—H19B	109.5	C27—C28—Br1	119.07 (13)
H19A—C19—H19B	109.5	C28—C29—C30	118.97 (16)
C16—C19—H19C	109.5	C28—C29—H29	120.5
H19A—C19—H19C	109.5	C30—C29—H29	120.5
H19B—C19—H19C	109.5	C25—C30—C29	120.66 (16)
C22A—C20—C13	113.32 (17)	C25—C30—H30	119.7
C23B—C20—C13	116.4 (2)	C29—C30—H30	119.7
C22A—C20—C23A	111.0 (2)
C10—N3—C4—C9	−175.87 (15)	N3—C10—C15—C14	−178.10 (16)
C10—N3—C4—C5	2.32 (17)	C11—C10—C15—C14	1.7 (2)
N3—C4—C5—C6	178.89 (13)	C6—C7—C16—C19	2.2 (2)
C9—C4—C5—C6	−2.7 (2)	C8—C7—C16—C19	−178.06 (16)
N3—C4—C5—C11	−1.96 (16)	C6—C7—C16—C17	−119.19 (18)
C9—C4—C5—C11	176.41 (14)	C8—C7—C16—C17	60.5 (2)
C4—C5—C6—C7	2.6 (2)	C6—C7—C16—C18	121.64 (17)
C11—C5—C6—C7	−176.26 (16)	C8—C7—C16—C18	−58.7 (2)
C5—C6—C7—C8	−0.6 (2)	C12—C13—C20—C22A	2.2 (3)
C5—C6—C7—C16	179.10 (14)	C14—C13—C20—C22A	−176.9 (2)
C6—C7—C8—C9	−1.4 (2)	C12—C13—C20—C23B	−174.8 (3)
C16—C7—C8—C9	178.89 (15)	C14—C13—C20—C23B	6.2 (3)
C7—C8—C9—C4	1.3 (2)	C12—C13—C20—C23A	−121.4 (2)
C7—C8—C9—C24	−179.34 (15)	C14—C13—C20—C23A	59.5 (2)
N3—C4—C9—C8	178.81 (15)	C12—C13—C20—C21B	61.9 (3)
C5—C4—C9—C8	0.8 (2)	C14—C13—C20—C21B	−117.1 (2)
N3—C4—C9—C24	−0.6 (3)	C12—C13—C20—C21A	123.2 (2)
C5—C4—C9—C24	−178.55 (14)	C14—C13—C20—C21A	−55.9 (2)
C4—N3—C10—C15	178.11 (16)	C12—C13—C20—C22B	−52.8 (3)
C4—N3—C10—C11	−1.74 (17)	C14—C13—C20—C22B	128.1 (2)
C15—C10—C11—C12	−1.3 (2)	C25—N2—C24—C9	−178.58 (14)
N3—C10—C11—C12	178.55 (13)	C8—C9—C24—N2	177.08 (15)
C15—C10—C11—C5	−179.37 (14)	C4—C9—C24—N2	−3.6 (2)
N3—C10—C11—C5	0.50 (17)	C24—N2—C25—C30	48.4 (2)
C6—C5—C11—C12	2.2 (3)	C24—N2—C25—C26	−134.37 (16)
C4—C5—C11—C12	−176.82 (16)	C30—C25—C26—C27	−4.4 (2)
C6—C5—C11—C10	179.87 (16)	N2—C25—C26—C27	178.28 (14)
C4—C5—C11—C10	0.88 (16)	C25—C26—C27—C28	2.5 (2)
C10—C11—C12—C13	−0.1 (2)	C26—C27—C28—C29	1.3 (3)
C5—C11—C12—C13	177.38 (15)	C26—C27—C28—Br1	−178.58 (12)
C11—C12—C13—C14	0.9 (2)	C27—C28—C29—C30	−3.1 (3)
C11—C12—C13—C20	−178.14 (14)	Br1—C28—C29—C30	176.80 (13)
C12—C13—C14—C15	−0.5 (2)	C26—C25—C30—C29	2.5 (3)
C20—C13—C14—C15	178.59 (15)	N2—C25—C30—C29	179.78 (15)
C13—C14—C15—C10	−0.8 (2)	C28—C29—C30—C25	1.1 (3)

Hydrogen-bond geometry (Å, º)

Cg1, Cg2 and Cg3 are the centroids of the C25–C30, C4–C9 and N3/C4/C5/C11/C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2	0.76 (2)	2.39 (2)	2.862 (2)	121.3 (16)
C22A—H22C···Cg1^i	0.96	2.92	3.878 (4)	177
C29—H29···Cg2^ii	0.93	2.95	3.613 (2)	129
C21B—H21E···Cg1^i	0.96	2.62	3.391 (5)	138
C22B—H22D···Cg3^iii	0.96	2.92	3.839 (5)	159

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