2-Bromo-5-tert-butyl-N-methyl-N-[2-(methyl-amino)-phen-yl]-3-(1-methyl-1H-benzimidazol-2-yl)benzamide.

In the title compound, C27H29BrN4O, benzimidazole ring system and the amide moiety are planar [r.m.s. deviations = 0.016 (2) and 0.017 (1) Å, respectively]. The mol-ecule adopts a conformation in which the amide linkage is almost perpendicular to the central ring [dihedral angle = 85.79 (8)°], while the benzimidazole ring system makes a dihedral angle of 70.26 (11)° with the central ring. In the crystal, the mol-ecules form dimers through N-H⋯O hydrogen bonds and C-H⋯O interactions. These dimers are further linked into zigzag ribbons along [201] by weak C-H⋯Br inter-actions. As a result of the bulky nature of the mol-ecule, as evidenced by the large dihedral angles between rings, there is little evidence for any π-π inter-actions.

Related literature

The metal binding properties of imidazole-containing pincer ligands can be modified by the type of donor atoms and the electron-withdrawing and electron-releasing character of their substituents, see: Selander & Szabó (2011 ▶). For the effect of N-substitution on the catalytic activity of phosphinoimidazolines in palladium-catalysed Heck reactions, see: Busacca et al. (2003 ▶). For the use of bromine-substituted benzimidazole in Heck reactions, see: Reddy & Krishna (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the preparation of the precursor, 2-bromo-5-(tert-but­yl)isophthalic acid, see: Field et al. (2003 ▶).

Experimental

Crystal data

C27H29BrN4O

M = 505.45

Monoclinic,

a = 34.4327 (13) Å

b = 9.4152 (2) Å

c = 17.1092 (7) Å

β = 118.312 (5)°

V = 4883.2 (3) Å3

Z = 8

Cu Kα radiation

μ = 2.50 mm−1

T = 123 K

0.38 × 0.32 × 0.23 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.788, T max = 1.000

9307 measured reflections

4929 independent reflections

4100 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.03

4929 reflections

308 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814014433/jj2190sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014433/jj2190Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014433/jj2190Isup3.cml

CCDC reference: 1009070

Additional supporting information: crystallographic information; 3D view; checkCIF report

C27H29BrN4O	F(000) = 2096
Mr = 505.45	Dx = 1.375 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 4036 reflections
a = 34.4327 (13) Å	θ = 2.9–75.5°
b = 9.4152 (2) Å	µ = 2.50 mm−1
c = 17.1092 (7) Å	T = 123 K
β = 118.312 (5)°	Prism, colorless
V = 4883.2 (3) Å3	0.38 × 0.32 × 0.23 mm
Z = 8

Agilent Xcalibur Ruby Gemini diffractometer	4929 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4100 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.5081 pixels mm-1	θmax = 75.6°, θmin = 2.9°
ω scans	h = −42→42
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −8→11
Tmin = 0.788, Tmax = 1.000	l = −20→21
9307 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.4711P] where P = (Fo2 + 2Fc2)/3
4929 reflections	(Δ/σ)max = 0.004
308 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. 1H NMR (400 MHz, CDCl3): δ (ppm) 7.87-7.71 (1H, m), 7.46-7.31 (4H, m), 7.09-7.07 (1H, m), 6.54-6.48 (1H, m), 3.53 (2H, s), 3.45 (2H, s), 2.89 (2H, s), 1.38 (1H, s), 1.13 (6H, s). 13C NMR (CDCl3): δ 29.4, 30.9, 31.1, 31.9, 31.2, 34.7, 35.1, 35.5, 53.9, 109.7, 109.9, 120.2, 122.1, 122.5, 122.7, 123.1, 123.3, 129.4, 129.7, 131.2, 133.0, 135.6, 142.8, 151.7, 152.6, 152.8.

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.

	x	y	z	Uiso*/Ueq
Br	0.630352 (8)	0.53882 (3)	0.543344 (15)	0.03435 (9)
O1	0.52147 (5)	0.66100 (17)	0.36987 (11)	0.0338 (3)
N1	0.70366 (6)	0.3018 (2)	0.53797 (13)	0.0370 (4)
N2	0.65609 (7)	0.1320 (2)	0.53017 (14)	0.0380 (4)
N3	0.56938 (7)	0.7887 (2)	0.19074 (15)	0.0406 (5)
H3B	0.5490 (9)	0.765 (3)	0.1989 (18)	0.033 (7)*
N4	0.57538 (6)	0.78517 (19)	0.36118 (13)	0.0315 (4)
C1	0.72063 (8)	0.4328 (3)	0.52039 (19)	0.0447 (6)
H1A	0.6998	0.4684	0.4614	0.067*
H1B	0.7492	0.4142	0.5227	0.067*
H1C	0.7244	0.5039	0.5653	0.067*
C2	0.72791 (8)	0.2049 (3)	0.60366 (16)	0.0401 (5)
C3	0.77297 (9)	0.1991 (4)	0.66449 (19)	0.0541 (7)
H3A	0.7929	0.2717	0.6682	0.065*
C4	0.78664 (11)	0.0803 (4)	0.7190 (2)	0.0620 (9)
H4A	0.8171	0.0697	0.7600	0.074*
C5	0.75708 (12)	−0.0240 (4)	0.7155 (2)	0.0615 (8)
H5A	0.7679	−0.1020	0.7554	0.074*
C6	0.71279 (11)	−0.0174 (3)	0.6561 (2)	0.0542 (7)
H6A	0.6929	−0.0892	0.6541	0.065*
C7	0.69805 (8)	0.1004 (3)	0.59819 (16)	0.0402 (5)
C8	0.66112 (7)	0.2518 (2)	0.49703 (15)	0.0323 (4)
C9	0.62557 (7)	0.3270 (2)	0.42009 (14)	0.0292 (4)
C10	0.60873 (7)	0.2663 (2)	0.33589 (15)	0.0300 (4)
H10A	0.6198	0.1769	0.3297	0.036*
C11	0.57614 (7)	0.3331 (2)	0.26044 (14)	0.0292 (4)
C12	0.55997 (7)	0.4627 (2)	0.27251 (15)	0.0294 (4)
H12A	0.5371	0.5086	0.2224	0.035*
C13	0.57612 (6)	0.5266 (2)	0.35517 (14)	0.0264 (4)
C14	0.60895 (7)	0.4577 (2)	0.42851 (14)	0.0276 (4)
C15	0.55815 (8)	0.2676 (2)	0.16780 (16)	0.0358 (5)
C16	0.59482 (11)	0.1859 (3)	0.15917 (19)	0.0543 (7)
H16A	0.6042	0.1043	0.1996	0.081*
H16B	0.6200	0.2490	0.1744	0.081*
H16C	0.5835	0.1524	0.0980	0.081*
C17	0.52108 (12)	0.1646 (4)	0.1534 (2)	0.0693 (11)
H17A	0.4978	0.2157	0.1592	0.104*
H17B	0.5328	0.0888	0.1979	0.104*
H17C	0.5089	0.1232	0.0938	0.104*
C18	0.54015 (8)	0.3820 (3)	0.09601 (15)	0.0363 (5)
H18A	0.5131	0.4223	0.0925	0.054*
H18B	0.5336	0.3400	0.0387	0.054*
H18C	0.5622	0.4573	0.1108	0.054*
C19	0.55554 (7)	0.6638 (2)	0.36324 (13)	0.0275 (4)
C20	0.55836 (9)	0.9201 (2)	0.3754 (2)	0.0426 (6)
H20A	0.5362	0.9011	0.3947	0.064*
H20B	0.5448	0.9743	0.3199	0.064*
H20C	0.5827	0.9751	0.4212	0.064*
C21	0.61458 (7)	0.7918 (2)	0.35017 (17)	0.0326 (5)
C22	0.65527 (8)	0.8083 (3)	0.42439 (18)	0.0414 (5)
H22A	0.6574	0.8092	0.4818	0.050*
C23	0.69305 (8)	0.8234 (3)	0.4155 (2)	0.0511 (7)
H23A	0.7211	0.8336	0.4664	0.061*
C24	0.68929 (8)	0.8235 (3)	0.3315 (2)	0.0507 (7)
H24A	0.7151	0.8333	0.3251	0.061*
C25	0.64900 (8)	0.8098 (3)	0.2569 (2)	0.0435 (6)
H25A	0.6474	0.8101	0.2000	0.052*
C26	0.60991 (7)	0.7951 (2)	0.26395 (17)	0.0346 (5)
C27	0.56379 (9)	0.7866 (3)	0.10141 (18)	0.0464 (6)
H27A	0.5323	0.7794	0.0588	0.070*
H27B	0.5795	0.7047	0.0945	0.070*
H27C	0.5758	0.8743	0.0905	0.070*

	U11	U22	U33	U12	U13	U23
Br	0.03690 (13)	0.03680 (13)	0.02700 (13)	0.00268 (9)	0.01323 (10)	−0.00251 (9)
O1	0.0297 (7)	0.0358 (8)	0.0387 (8)	−0.0016 (6)	0.0186 (7)	−0.0021 (7)
N1	0.0310 (9)	0.0397 (10)	0.0355 (10)	0.0022 (8)	0.0118 (8)	0.0008 (9)
N2	0.0409 (10)	0.0310 (9)	0.0377 (10)	0.0037 (8)	0.0151 (9)	0.0023 (8)
N3	0.0332 (10)	0.0481 (12)	0.0406 (11)	−0.0087 (9)	0.0175 (9)	−0.0048 (9)
N4	0.0269 (9)	0.0257 (8)	0.0416 (10)	0.0007 (7)	0.0159 (8)	−0.0004 (8)
C1	0.0359 (12)	0.0481 (14)	0.0495 (15)	−0.0062 (11)	0.0196 (12)	−0.0017 (12)
C2	0.0389 (12)	0.0445 (13)	0.0324 (12)	0.0115 (10)	0.0132 (10)	0.0003 (10)
C3	0.0398 (14)	0.072 (2)	0.0381 (14)	0.0112 (13)	0.0085 (12)	−0.0019 (14)
C4	0.0498 (16)	0.083 (2)	0.0357 (14)	0.0283 (16)	0.0059 (13)	0.0053 (15)
C5	0.071 (2)	0.0625 (19)	0.0414 (15)	0.0313 (17)	0.0189 (15)	0.0140 (14)
C6	0.0675 (19)	0.0453 (15)	0.0460 (15)	0.0195 (14)	0.0237 (15)	0.0108 (12)
C7	0.0439 (13)	0.0377 (12)	0.0349 (12)	0.0119 (10)	0.0153 (11)	0.0026 (10)
C8	0.0334 (11)	0.0304 (10)	0.0312 (11)	0.0043 (9)	0.0138 (9)	−0.0007 (9)
C9	0.0270 (10)	0.0282 (10)	0.0307 (11)	−0.0011 (8)	0.0124 (9)	0.0003 (8)
C10	0.0302 (10)	0.0243 (9)	0.0355 (11)	−0.0010 (8)	0.0155 (9)	−0.0012 (8)
C11	0.0321 (10)	0.0241 (9)	0.0313 (11)	−0.0072 (8)	0.0150 (9)	−0.0027 (8)
C12	0.0292 (10)	0.0267 (10)	0.0294 (10)	−0.0019 (8)	0.0115 (9)	0.0023 (8)
C13	0.0246 (9)	0.0239 (9)	0.0302 (10)	−0.0031 (8)	0.0125 (8)	−0.0007 (8)
C14	0.0279 (10)	0.0289 (10)	0.0249 (10)	−0.0031 (8)	0.0117 (8)	−0.0022 (8)
C15	0.0483 (13)	0.0268 (10)	0.0300 (11)	−0.0073 (10)	0.0167 (10)	−0.0028 (9)
C16	0.082 (2)	0.0392 (13)	0.0388 (14)	0.0177 (14)	0.0262 (15)	0.0001 (11)
C17	0.089 (2)	0.071 (2)	0.0360 (14)	−0.053 (2)	0.0204 (16)	−0.0103 (14)
C18	0.0436 (12)	0.0350 (11)	0.0307 (11)	0.0006 (10)	0.0179 (10)	−0.0003 (9)
C19	0.0249 (9)	0.0289 (10)	0.0242 (10)	0.0005 (8)	0.0080 (8)	−0.0015 (8)
C20	0.0406 (12)	0.0276 (11)	0.0617 (16)	0.0050 (10)	0.0261 (12)	0.0003 (11)
C21	0.0271 (10)	0.0223 (9)	0.0484 (13)	−0.0001 (8)	0.0179 (10)	0.0013 (9)
C22	0.0332 (12)	0.0383 (12)	0.0450 (14)	−0.0049 (10)	0.0123 (11)	0.0063 (11)
C23	0.0282 (12)	0.0508 (15)	0.0623 (18)	−0.0053 (11)	0.0116 (12)	0.0077 (13)
C24	0.0316 (12)	0.0470 (14)	0.077 (2)	−0.0034 (11)	0.0282 (13)	0.0031 (14)
C25	0.0407 (13)	0.0375 (12)	0.0617 (16)	−0.0055 (10)	0.0320 (13)	−0.0044 (12)
C26	0.0310 (11)	0.0244 (9)	0.0477 (13)	−0.0018 (8)	0.0182 (10)	−0.0021 (9)
C27	0.0515 (15)	0.0427 (13)	0.0443 (14)	−0.0125 (12)	0.0221 (12)	−0.0076 (11)

Br—C14	1.901 (2)	C12—C13	1.388 (3)
O1—C19	1.232 (3)	C12—H12A	0.9500
N1—C8	1.373 (3)	C13—C14	1.389 (3)
N1—C2	1.379 (3)	C13—C19	1.510 (3)
N1—C1	1.456 (3)	C15—C18	1.526 (3)
N2—C8	1.310 (3)	C15—C17	1.527 (3)
N2—C7	1.391 (3)	C15—C16	1.545 (4)
N3—C26	1.365 (3)	C16—H16A	0.9800
N3—C27	1.447 (3)	C16—H16B	0.9800
N3—H3B	0.81 (3)	C16—H16C	0.9800
N4—C19	1.340 (3)	C17—H17A	0.9800
N4—C21	1.450 (3)	C17—H17B	0.9800
N4—C20	1.467 (3)	C17—H17C	0.9800
C1—H1A	0.9800	C18—H18A	0.9800
C1—H1B	0.9800	C18—H18B	0.9800
C1—H1C	0.9800	C18—H18C	0.9800
C2—C7	1.394 (4)	C20—H20A	0.9800
C2—C3	1.401 (4)	C20—H20B	0.9800
C3—C4	1.388 (5)	C20—H20C	0.9800
C3—H3A	0.9500	C21—C22	1.383 (3)
C4—C5	1.395 (5)	C21—C26	1.406 (3)
C4—H4A	0.9500	C22—C23	1.387 (3)
C5—C6	1.376 (5)	C22—H22A	0.9500
C5—H5A	0.9500	C23—C24	1.379 (4)
C6—C7	1.412 (4)	C23—H23A	0.9500
C6—H6A	0.9500	C24—C25	1.375 (4)
C8—C9	1.484 (3)	C24—H24A	0.9500
C9—C14	1.393 (3)	C25—C26	1.414 (3)
C9—C10	1.395 (3)	C25—H25A	0.9500
C10—C11	1.395 (3)	C27—H27A	0.9800
C10—H10A	0.9500	C27—H27B	0.9800
C11—C12	1.396 (3)	C27—H27C	0.9800
C11—C15	1.531 (3)
C8—N1—C2	106.0 (2)	C18—C15—C11	111.07 (18)
C8—N1—C1	128.4 (2)	C17—C15—C11	108.6 (2)
C2—N1—C1	125.5 (2)	C18—C15—C16	108.3 (2)
C8—N2—C7	104.4 (2)	C17—C15—C16	109.0 (3)
C26—N3—C27	122.4 (2)	C11—C15—C16	110.6 (2)
C26—N3—H3B	117 (2)	C15—C16—H16A	109.5
C27—N3—H3B	119 (2)	C15—C16—H16B	109.5
C19—N4—C21	123.86 (18)	H16A—C16—H16B	109.5
C19—N4—C20	119.04 (18)	C15—C16—H16C	109.5
C21—N4—C20	117.02 (18)	H16A—C16—H16C	109.5
N1—C1—H1A	109.5	H16B—C16—H16C	109.5
N1—C1—H1B	109.5	C15—C17—H17A	109.5
H1A—C1—H1B	109.5	C15—C17—H17B	109.5
N1—C1—H1C	109.5	H17A—C17—H17B	109.5
H1A—C1—H1C	109.5	C15—C17—H17C	109.5
H1B—C1—H1C	109.5	H17A—C17—H17C	109.5
N1—C2—C7	105.7 (2)	H17B—C17—H17C	109.5
N1—C2—C3	131.4 (3)	C15—C18—H18A	109.5
C7—C2—C3	123.0 (3)	C15—C18—H18B	109.5
C4—C3—C2	115.7 (3)	H18A—C18—H18B	109.5
C4—C3—H3A	122.1	C15—C18—H18C	109.5
C2—C3—H3A	122.1	H18A—C18—H18C	109.5
C3—C4—C5	122.0 (3)	H18B—C18—H18C	109.5
C3—C4—H4A	119.0	O1—C19—N4	122.7 (2)
C5—C4—H4A	119.0	O1—C19—C13	119.92 (19)
C6—C5—C4	122.0 (3)	N4—C19—C13	117.37 (17)
C6—C5—H5A	119.0	N4—C20—H20A	109.5
C4—C5—H5A	119.0	N4—C20—H20B	109.5
C5—C6—C7	117.2 (3)	H20A—C20—H20B	109.5
C5—C6—H6A	121.4	N4—C20—H20C	109.5
C7—C6—H6A	121.4	H20A—C20—H20C	109.5
N2—C7—C2	110.2 (2)	H20B—C20—H20C	109.5
N2—C7—C6	129.8 (3)	C22—C21—C26	121.5 (2)
C2—C7—C6	120.0 (3)	C22—C21—N4	119.1 (2)
N2—C8—N1	113.7 (2)	C26—C21—N4	119.1 (2)
N2—C8—C9	124.9 (2)	C21—C22—C23	120.3 (3)
N1—C8—C9	121.4 (2)	C21—C22—H22A	119.8
C14—C9—C10	118.6 (2)	C23—C22—H22A	119.8
C14—C9—C8	122.40 (19)	C24—C23—C22	119.0 (3)
C10—C9—C8	119.00 (19)	C24—C23—H23A	120.5
C9—C10—C11	121.9 (2)	C22—C23—H23A	120.5
C9—C10—H10A	119.0	C25—C24—C23	121.4 (2)
C11—C10—H10A	119.0	C25—C24—H24A	119.3
C10—C11—C12	117.3 (2)	C23—C24—H24A	119.3
C10—C11—C15	121.96 (19)	C24—C25—C26	120.8 (3)
C12—C11—C15	120.7 (2)	C24—C25—H25A	119.6
C13—C12—C11	122.3 (2)	C26—C25—H25A	119.6
C13—C12—H12A	118.8	N3—C26—C21	121.4 (2)
C11—C12—H12A	118.8	N3—C26—C25	121.8 (2)
C12—C13—C14	118.62 (19)	C21—C26—C25	116.8 (2)
C12—C13—C19	119.05 (19)	N3—C27—H27A	109.5
C14—C13—C19	122.21 (19)	N3—C27—H27B	109.5
C13—C14—C9	121.17 (19)	H27A—C27—H27B	109.5
C13—C14—Br	119.78 (16)	N3—C27—H27C	109.5
C9—C14—Br	119.01 (16)	H27A—C27—H27C	109.5
C18—C15—C17	109.2 (2)	H27B—C27—H27C	109.5
C8—N1—C2—C7	0.1 (2)	C12—C13—C14—Br	−177.74 (14)
C1—N1—C2—C7	177.6 (2)	C19—C13—C14—Br	−1.6 (3)
C8—N1—C2—C3	178.1 (3)	C10—C9—C14—C13	0.4 (3)
C1—N1—C2—C3	−4.3 (4)	C8—C9—C14—C13	179.08 (19)
N1—C2—C3—C4	−176.7 (3)	C10—C9—C14—Br	178.12 (15)
C7—C2—C3—C4	1.0 (4)	C8—C9—C14—Br	−3.2 (3)
C2—C3—C4—C5	−2.2 (4)	C10—C11—C15—C18	−154.3 (2)
C3—C4—C5—C6	1.9 (5)	C12—C11—C15—C18	26.3 (3)
C4—C5—C6—C7	−0.2 (5)	C10—C11—C15—C17	85.6 (3)
C8—N2—C7—C2	−0.3 (3)	C12—C11—C15—C17	−93.8 (3)
C8—N2—C7—C6	−178.8 (3)	C10—C11—C15—C16	−34.1 (3)
N1—C2—C7—N2	0.1 (3)	C12—C11—C15—C16	146.5 (2)
C3—C2—C7—N2	−178.1 (2)	C21—N4—C19—O1	−177.7 (2)
N1—C2—C7—C6	178.7 (2)	C20—N4—C19—O1	5.7 (3)
C3—C2—C7—C6	0.5 (4)	C21—N4—C19—C13	1.1 (3)
C5—C6—C7—N2	177.4 (3)	C20—N4—C19—C13	−175.5 (2)
C5—C6—C7—C2	−0.9 (4)	C12—C13—C19—O1	82.7 (3)
C7—N2—C8—N1	0.4 (3)	C14—C13—C19—O1	−93.4 (2)
C7—N2—C8—C9	177.9 (2)	C12—C13—C19—N4	−96.1 (2)
C2—N1—C8—N2	−0.3 (3)	C14—C13—C19—N4	87.7 (2)
C1—N1—C8—N2	−177.8 (2)	C19—N4—C21—C22	−98.6 (3)
C2—N1—C8—C9	−177.9 (2)	C20—N4—C21—C22	78.2 (3)
C1—N1—C8—C9	4.6 (4)	C19—N4—C21—C26	87.6 (3)
N2—C8—C9—C14	112.4 (3)	C20—N4—C21—C26	−95.7 (3)
N1—C8—C9—C14	−70.3 (3)	C26—C21—C22—C23	−2.4 (4)
N2—C8—C9—C10	−68.9 (3)	N4—C21—C22—C23	−176.1 (2)
N1—C8—C9—C10	108.4 (2)	C21—C22—C23—C24	0.8 (4)
C14—C9—C10—C11	0.4 (3)	C22—C23—C24—C25	0.4 (4)
C8—C9—C10—C11	−178.28 (19)	C23—C24—C25—C26	0.1 (4)
C9—C10—C11—C12	−1.6 (3)	C27—N3—C26—C21	−177.6 (2)
C9—C10—C11—C15	179.03 (19)	C27—N3—C26—C25	4.3 (4)
C10—C11—C12—C13	2.0 (3)	C22—C21—C26—N3	−175.4 (2)
C15—C11—C12—C13	−178.63 (19)	N4—C21—C26—N3	−1.7 (3)
C11—C12—C13—C14	−1.2 (3)	C22—C21—C26—C25	2.8 (3)
C11—C12—C13—C19	−177.46 (18)	N4—C21—C26—C25	176.5 (2)
C12—C13—C14—C9	0.0 (3)	C24—C25—C26—N3	176.5 (2)
C19—C13—C14—C9	176.10 (18)	C24—C25—C26—C21	−1.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1i	0.81 (3)	2.35 (3)	3.038 (3)	143 (3)
C4—H4A···Brii	0.95	2.98	3.719 (3)	135
C12—H12A···O1i	0.95	2.37	3.287 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1i	0.81 (3)	2.35 (3)	3.038 (3)	143 (3)
C4—H4A⋯Brii	0.95	2.98	3.719 (3)	135
C12—H12A⋯O1i	0.95	2.37	3.287 (3)	163

Symmetry codes: (i) ; (ii) .