π-stacking and C—X...D (X = H, NO₂; D = O, π) inter­actions in the crystal network of both C—H...N and π-stacked dimers of 1,2-bis­(4-bromo­phenyl)-1H-benzimidazole and 2-(4-bromo­phenyl)-1-(4-nitro­phenyl)-1H-benzimidazole

Mol­ecules of 1,2-bis­(4-bromo­phenyl)-1H-benzimidazole, C₁₉H₁₂Br₂N₂, (I), and 2-(4-bromo­phenyl)-1-(4-nitro­phenyl)-1H-benzimidazole, C₁₉H₁₂BrN₃O₂, (II), are arranged in dimeric units through C—H...N and parallel-displaced π-stacking inter­actions favoured by the appropriate disposition of N- and C-bonded phenyl rings with respect to the mean benzimidazole plane. The mol­ecular packing of the dimers of (I) and (II) arises by the concurrence of a diverse set of weak inter­molecular C—X...D (X = H, NO₂; D = O, π) inter­actions.

Computing details

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), WinGX2003 (Farrugia, 2012) and publCIF (Westrip, 2010) for (I); SHELXL97 (Sheldrick, 2008), and WinGX2003 (Farrugia, 2012) and publCIF (Westrip, 2010) for (II).

(I) 1,2-Bis(4-bromophenyl)-1H-benzimidazole

Crystal data

C19H12Br2N2	Z = 2
Mr = 428.13	F(000) = 420
Triclinic, P1	Dx = 1.713 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.6621 (5) Å	Cell parameters from 600 reflections
b = 10.8241 (7) Å	θ = 20–25°
c = 11.0422 (7) Å	µ = 6.18 mm^−1
α = 105.078 (6)°	T = 293 K
β = 106.456 (6)°	Block, colourless
γ = 96.677 (5)°	0.30 × 0.26 × 0.24 × 0.15 (radius) mm
V = 830.00 (9) Å^3

Data collection

Oxford Xcalibur Ruby Gemini diffractometer	3743 independent reflections
Radiation source: fine-focus sealed tube	2586 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scans	θmax = 88.7°, θmin = 6.8°
Absorption correction: for a sphere (Dwiggins, 1975)	h = −9→9
Tmin = 0.278, Tmax = 0.360	k = −14→13
12778 measured reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0717P)^2] where P = (Fo^2 + 2Fc^2)/3
3743 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.95 e Å^−3
0 restraints	Δρmin = −0.61 e Å^−3

Special details

Experimental. Interpolation using International Tables Vol. C (1992) p. 523, Table 6.3.3.3 for values of muR in the range 0–2.5, and International Tables Vol. II (1959) p. 302, Table 5.3.6B for muR in the range 2.6–10.0. The interpolation procedure of C. W. Dwiggins Jr [Acta Cryst. (1975) A31, 146–148] is used with some modification.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
Br13	0.79691 (5)	1.06330 (4)	0.37402 (4)	0.0578 (2)
Br19	0.27246 (8)	0.31022 (5)	0.53911 (5)	0.0743 (2)
N1	0.0150 (4)	0.7327 (3)	0.1590 (3)	0.0445 (10)
N3	−0.2154 (4)	0.5539 (3)	0.0613 (3)	0.0506 (11)
C2	−0.0499 (5)	0.6033 (3)	0.1501 (3)	0.0456 (12)
C4	−0.4298 (6)	0.6530 (5)	−0.0892 (4)	0.0618 (14)
C5	−0.4474 (6)	0.7648 (5)	−0.1212 (4)	0.0706 (18)
C6	−0.3039 (6)	0.8790 (5)	−0.0575 (5)	0.0685 (17)
C7	−0.1426 (6)	0.8787 (4)	0.0360 (4)	0.0550 (12)
C8	−0.1251 (5)	0.7645 (4)	0.0674 (3)	0.0450 (11)
C9	−0.2665 (5)	0.6523 (4)	0.0072 (3)	0.0488 (12)
C10	0.2012 (5)	0.8076 (3)	0.2149 (3)	0.0403 (11)
C11	0.2371 (5)	0.9339 (3)	0.2995 (3)	0.0438 (11)
C12	0.4150 (5)	1.0091 (3)	0.3460 (3)	0.0456 (11)
C13	0.5540 (5)	0.9570 (3)	0.3094 (3)	0.0409 (11)
C14	0.5201 (5)	0.8317 (3)	0.2268 (4)	0.0474 (12)
C15	0.3435 (5)	0.7565 (3)	0.1794 (4)	0.0466 (11)
C16	0.0443 (5)	0.5365 (3)	0.2413 (4)	0.0453 (12)
C17	0.1621 (6)	0.6025 (4)	0.3688 (4)	0.0581 (16)
C18	0.2324 (6)	0.5361 (4)	0.4575 (4)	0.0633 (17)
C19	0.1843 (6)	0.4016 (4)	0.4168 (4)	0.0539 (14)
C20	0.0694 (7)	0.3340 (4)	0.2901 (4)	0.0647 (16)
C21	−0.0014 (6)	0.4003 (4)	0.2028 (4)	0.0575 (14)
H4	−0.52423	0.57870	−0.13044	0.0744*
H5	−0.55469	0.76679	−0.18576	0.0848*
H6	−0.31997	0.95505	−0.07979	0.0821*
H7	−0.04811	0.95290	0.07694	0.0658*
H11	0.14224	0.96781	0.32476	0.0524*
H12	0.44014	1.09446	0.40175	0.0547*
H14	0.61598	0.79774	0.20310	0.0570*
H15	0.31955	0.67134	0.12340	0.0557*
H17	0.19485	0.69329	0.39554	0.0695*
H18	0.31078	0.58167	0.54313	0.0760*
H20	0.03949	0.24319	0.26320	0.0775*
H21	−0.08029	0.35394	0.11748	0.0693*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br13	0.0380 (3)	0.0566 (3)	0.0641 (3)	−0.0054 (2)	0.0143 (2)	0.0033 (2)
Br19	0.0863 (4)	0.0669 (3)	0.0877 (4)	0.0334 (3)	0.0341 (3)	0.0398 (3)
N1	0.0392 (16)	0.0431 (17)	0.0486 (17)	−0.0007 (13)	0.0152 (14)	0.0127 (14)
N3	0.0422 (18)	0.0495 (19)	0.0511 (18)	−0.0052 (15)	0.0152 (15)	0.0072 (15)
C2	0.046 (2)	0.041 (2)	0.046 (2)	−0.0018 (16)	0.0211 (18)	0.0050 (16)
C4	0.044 (2)	0.080 (3)	0.049 (2)	−0.007 (2)	0.008 (2)	0.016 (2)
C5	0.049 (2)	0.093 (4)	0.068 (3)	0.002 (2)	0.004 (2)	0.044 (3)
C6	0.061 (3)	0.079 (3)	0.070 (3)	0.009 (2)	0.014 (2)	0.041 (2)
C7	0.049 (2)	0.059 (2)	0.058 (2)	0.0007 (19)	0.016 (2)	0.026 (2)
C8	0.0385 (19)	0.053 (2)	0.0431 (19)	0.0009 (16)	0.0155 (16)	0.0153 (17)
C9	0.043 (2)	0.055 (2)	0.045 (2)	−0.0026 (17)	0.0177 (18)	0.0117 (18)
C10	0.0401 (19)	0.0387 (19)	0.0401 (19)	0.0013 (15)	0.0139 (16)	0.0110 (15)
C11	0.0391 (19)	0.043 (2)	0.048 (2)	0.0106 (15)	0.0166 (16)	0.0082 (16)
C12	0.047 (2)	0.0364 (19)	0.045 (2)	0.0057 (16)	0.0123 (17)	0.0027 (15)
C13	0.0343 (18)	0.0405 (19)	0.0401 (18)	−0.0007 (15)	0.0080 (15)	0.0078 (15)
C14	0.043 (2)	0.045 (2)	0.053 (2)	0.0098 (16)	0.0215 (18)	0.0065 (17)
C15	0.049 (2)	0.0353 (19)	0.051 (2)	0.0029 (16)	0.0200 (18)	0.0043 (16)
C16	0.045 (2)	0.041 (2)	0.050 (2)	0.0036 (16)	0.0225 (18)	0.0089 (16)
C17	0.068 (3)	0.037 (2)	0.061 (3)	0.0049 (19)	0.016 (2)	0.0096 (18)
C18	0.068 (3)	0.053 (3)	0.058 (3)	0.009 (2)	0.010 (2)	0.012 (2)
C19	0.061 (2)	0.046 (2)	0.067 (3)	0.0195 (19)	0.031 (2)	0.023 (2)
C20	0.085 (3)	0.035 (2)	0.076 (3)	0.005 (2)	0.036 (3)	0.013 (2)
C21	0.069 (3)	0.040 (2)	0.056 (2)	−0.0013 (19)	0.023 (2)	0.0049 (18)

Geometric parameters (Å, º)

Br13—C13	1.903 (4)	C14—C15	1.374 (6)
Br19—C19	1.895 (4)	C16—C17	1.384 (6)
N1—C2	1.399 (5)	C16—C21	1.395 (6)
N1—C8	1.395 (5)	C17—C18	1.387 (6)
N1—C10	1.430 (5)	C18—C19	1.378 (6)
N3—C2	1.312 (5)	C19—C20	1.374 (6)
N3—C9	1.393 (5)	C20—C21	1.376 (6)
C2—C16	1.465 (5)	C4—H4	0.9300
C4—C5	1.357 (8)	C5—H5	0.9300
C4—C9	1.397 (6)	C6—H6	0.9300
C5—C6	1.423 (7)	C7—H7	0.9300
C6—C7	1.369 (7)	C11—H11	0.9300
C7—C8	1.379 (6)	C12—H12	0.9300
C8—C9	1.399 (6)	C14—H14	0.9300
C10—C11	1.386 (5)	C15—H15	0.9300
C10—C15	1.385 (6)	C17—H17	0.9300
C11—C12	1.383 (5)	C18—H18	0.9300
C12—C13	1.371 (5)	C20—H20	0.9300
C13—C14	1.371 (5)	C21—H21	0.9300
C2—N1—C8	105.9 (3)	C17—C18—C19	119.0 (4)
C2—N1—C10	128.8 (3)	Br19—C19—C18	119.3 (3)
C8—N1—C10	122.7 (3)	Br19—C19—C20	120.0 (3)
C2—N3—C9	106.2 (3)	C18—C19—C20	120.6 (4)
N1—C2—N3	112.2 (3)	C19—C20—C21	120.2 (4)
N1—C2—C16	123.8 (3)	C16—C21—C20	120.5 (4)
N3—C2—C16	123.5 (3)	C5—C4—H4	121.00
C5—C4—C9	118.4 (4)	C9—C4—H4	121.00
C4—C5—C6	121.0 (4)	C4—C5—H5	120.00
C5—C6—C7	121.1 (5)	C6—C5—H5	120.00
C6—C7—C8	117.7 (4)	C5—C6—H6	119.00
N1—C8—C7	132.2 (4)	C7—C6—H6	119.00
N1—C8—C9	106.0 (4)	C6—C7—H7	121.00
C7—C8—C9	121.8 (4)	C8—C7—H7	121.00
N3—C9—C4	130.2 (4)	C10—C11—H11	120.00
N3—C9—C8	109.6 (3)	C12—C11—H11	120.00
C4—C9—C8	120.1 (4)	C11—C12—H12	120.00
N1—C10—C11	119.7 (3)	C13—C12—H12	120.00
N1—C10—C15	120.1 (3)	C13—C14—H14	120.00
C11—C10—C15	120.1 (3)	C15—C14—H14	120.00
C10—C11—C12	119.5 (4)	C10—C15—H15	120.00
C11—C12—C13	119.6 (3)	C14—C15—H15	120.00
Br13—C13—C12	118.6 (2)	C16—C17—H17	119.00
Br13—C13—C14	120.1 (3)	C18—C17—H17	119.00
C12—C13—C14	121.3 (4)	C17—C18—H18	121.00
C13—C14—C15	119.6 (4)	C19—C18—H18	121.00
C10—C15—C14	120.0 (3)	C19—C20—H20	120.00
C2—C16—C17	122.9 (3)	C21—C20—H20	120.00
C2—C16—C21	118.4 (3)	C16—C21—H21	120.00
C17—C16—C21	118.4 (4)	C20—C21—H21	120.00
C16—C17—C18	121.4 (4)
C8—N1—C2—N3	0.4 (4)	C6—C7—C8—N1	−177.7 (4)
C10—N1—C2—N3	−161.6 (3)	C7—C8—C9—C4	1.1 (6)
C8—N1—C2—C16	−172.0 (3)	N1—C8—C9—N3	0.5 (4)
C10—N1—C2—C16	26.0 (6)	N1—C8—C9—C4	179.1 (3)
C2—N1—C8—C9	−0.5 (4)	C7—C8—C9—N3	−177.5 (4)
C10—N1—C8—C9	162.9 (3)	N1—C10—C11—C12	−175.5 (3)
C8—N1—C10—C11	67.2 (4)	C15—C10—C11—C12	1.2 (5)
C2—N1—C10—C15	49.8 (5)	N1—C10—C15—C14	175.9 (3)
C8—N1—C10—C15	−109.6 (4)	C11—C10—C15—C14	−0.8 (5)
C2—N1—C10—C11	−133.5 (4)	C10—C11—C12—C13	−1.0 (5)
C2—N1—C8—C7	177.2 (4)	C11—C12—C13—Br13	179.6 (2)
C10—N1—C8—C7	−19.5 (6)	C11—C12—C13—C14	0.4 (5)
C2—N3—C9—C8	−0.3 (4)	Br13—C13—C14—C15	−179.1 (3)
C9—N3—C2—C16	172.3 (3)	C12—C13—C14—C15	0.1 (5)
C2—N3—C9—C4	−178.7 (4)	C13—C14—C15—C10	0.2 (6)
C9—N3—C2—N1	0.0 (4)	C2—C16—C17—C18	172.6 (4)
N3—C2—C16—C21	26.2 (6)	C21—C16—C17—C18	−0.7 (7)
N1—C2—C16—C21	−162.4 (4)	C2—C16—C21—C20	−173.5 (4)
N3—C2—C16—C17	−147.1 (4)	C17—C16—C21—C20	0.1 (7)
N1—C2—C16—C17	24.3 (6)	C16—C17—C18—C19	0.4 (7)
C9—C4—C5—C6	−0.5 (7)	C17—C18—C19—Br19	−177.8 (4)
C5—C4—C9—C8	−0.6 (6)	C17—C18—C19—C20	0.4 (7)
C5—C4—C9—N3	177.6 (4)	Br19—C19—C20—C21	177.2 (4)
C4—C5—C6—C7	1.3 (7)	C18—C19—C20—C21	−1.0 (8)
C5—C6—C7—C8	−0.8 (7)	C19—C20—C21—C16	0.8 (8)
C6—C7—C8—C9	−0.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N3^i	0.93	2.60	3.525 (5)	171

Symmetry code: (i) −x, −y+1, −z.

(II) 2-(4-Bromophenyl)-1-(4-nitrophenyl)-1H-benzimidazole

Crystal data

C19H12BrN3O2	Z = 2
Mr = 394.23	F(000) = 396
Triclinic, P1	Dx = 1.540 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.8689 (4) Å	Cell parameters from 600 reflections
b = 10.0444 (4) Å	θ = 20–25°
c = 11.8867 (5) Å	µ = 3.44 mm^−1
α = 68.534 (4)°	T = 293 K
β = 76.677 (4)°	Block, pale yellow
γ = 86.869 (4)°	0.33 × 0.28 × 0.26 × 0.15 (radius) mm
V = 850.35 (7) Å^3

Data collection

Oxford Xcalibur Ruby Gemini diffractometer	3030 reflections with I > 2σ(I)
ω scans	Rint = 0.026
Absorption correction: for a sphere (Dwiggins, 1975)	θmax = 78.7°, θmin = 4.1°
Tmin = 0.482, Tmax = 0.527	h = −9→9
15531 measured reflections	k = −12→12
3560 independent reflections	l = −15→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0545P)^2 + 0.2882P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3560 reflections	Δρmax = 0.66 e Å^−3
227 parameters	Δρmin = −0.64 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (4)

Special details

Experimental. Interpolation using International Tables Vol. C (1992) p. 523, Table 6.3.3.3 for values of muR in the range 0–2.5, and International Tables Vol. II (1959) p. 302, Table 5.3.6B for muR in the range 2.6–10.0. The interpolation procedure of C. W. Dwiggins Jr [Acta Cryst. (1975) A31, 146–148] is used with some modification.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
Br19	0.60320 (6)	−0.13648 (4)	0.82836 (5)	0.1183 (2)
O13A	0.7074 (3)	0.3829 (3)	−0.0574 (2)	0.0966 (10)
O13B	0.9350 (3)	0.2692 (2)	−0.01132 (19)	0.0861 (8)
N1	0.7690 (2)	0.56674 (18)	0.38271 (15)	0.0494 (5)
N3	0.7743 (3)	0.5887 (2)	0.56310 (17)	0.0541 (6)
N13	0.8165 (3)	0.3464 (2)	0.00549 (17)	0.0657 (7)
C2	0.7574 (3)	0.4986 (2)	0.50915 (18)	0.0478 (6)
C4	0.8273 (4)	0.8556 (3)	0.4756 (3)	0.0723 (10)
C5	0.8505 (4)	0.9725 (3)	0.3676 (3)	0.0810 (10)
C6	0.8461 (4)	0.9605 (3)	0.2556 (3)	0.0789 (10)
C7	0.8192 (3)	0.8298 (3)	0.2468 (2)	0.0655 (8)
C8	0.7955 (3)	0.7120 (2)	0.3568 (2)	0.0529 (6)
C9	0.7992 (3)	0.7219 (2)	0.4700 (2)	0.0552 (7)
C10	0.7804 (3)	0.5068 (2)	0.28960 (17)	0.0465 (6)
C11	0.6561 (3)	0.5410 (3)	0.2189 (2)	0.0617 (8)
C12	0.6677 (3)	0.4881 (3)	0.1259 (2)	0.0641 (8)
C13	0.8037 (3)	0.4013 (2)	0.10580 (18)	0.0523 (6)
C14	0.9286 (3)	0.3662 (2)	0.17517 (19)	0.0514 (6)
C15	0.9178 (3)	0.4205 (2)	0.26803 (18)	0.0479 (6)
C16	0.7222 (3)	0.3448 (2)	0.57881 (18)	0.0483 (6)
C17	0.6422 (3)	0.2541 (3)	0.5397 (2)	0.0565 (7)
C18	0.6075 (3)	0.1116 (3)	0.6135 (3)	0.0676 (8)
C19	0.6509 (3)	0.0601 (3)	0.7270 (3)	0.0692 (8)
C20	0.7277 (3)	0.1465 (3)	0.7696 (2)	0.0687 (8)
C21	0.7630 (3)	0.2876 (3)	0.6953 (2)	0.0584 (7)
H4	0.83005	0.86468	0.55024	0.0867*
H5	0.86982	1.06217	0.36923	0.0970*
H6	0.86171	1.04261	0.18437	0.0947*
H7	0.81706	0.82164	0.17171	0.0786*
H11	0.56502	0.59955	0.23422	0.0740*
H12	0.58523	0.51061	0.07742	0.0769*
H14	1.01875	0.30689	0.15992	0.0617*
H15	1.00165	0.39932	0.31531	0.0575*
H17	0.61195	0.28999	0.46316	0.0678*
H18	0.55538	0.05133	0.58670	0.0811*
H20	0.75500	0.10999	0.84712	0.0824*
H21	0.81551	0.34674	0.72303	0.0701*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br19	0.1101 (3)	0.0678 (3)	0.1331 (4)	−0.0110 (2)	−0.0188 (3)	0.0108 (2)
O13A	0.1064 (17)	0.139 (2)	0.0682 (12)	−0.0022 (14)	−0.0304 (12)	−0.0578 (13)
O13B	0.1190 (17)	0.0811 (13)	0.0639 (10)	0.0078 (12)	−0.0073 (11)	−0.0416 (10)
N1	0.0547 (10)	0.0521 (9)	0.0435 (8)	0.0066 (7)	−0.0096 (7)	−0.0215 (7)
N3	0.0593 (10)	0.0600 (10)	0.0534 (9)	0.0094 (8)	−0.0177 (8)	−0.0306 (8)
N13	0.0830 (14)	0.0691 (12)	0.0439 (9)	−0.0152 (10)	−0.0015 (9)	−0.0247 (9)
C2	0.0469 (10)	0.0585 (11)	0.0440 (9)	0.0084 (8)	−0.0128 (8)	−0.0250 (9)
C4	0.0768 (17)	0.0651 (15)	0.0908 (18)	0.0109 (12)	−0.0260 (14)	−0.0436 (14)
C5	0.0857 (19)	0.0546 (14)	0.106 (2)	0.0044 (13)	−0.0191 (16)	−0.0349 (15)
C6	0.0808 (18)	0.0531 (13)	0.0867 (19)	0.0058 (12)	−0.0068 (14)	−0.0146 (12)
C7	0.0690 (15)	0.0605 (13)	0.0589 (13)	0.0097 (11)	−0.0073 (11)	−0.0178 (10)
C8	0.0502 (11)	0.0536 (11)	0.0562 (11)	0.0086 (9)	−0.0093 (9)	−0.0241 (9)
C9	0.0543 (12)	0.0570 (12)	0.0620 (12)	0.0096 (9)	−0.0157 (9)	−0.0300 (10)
C10	0.0478 (10)	0.0529 (10)	0.0390 (9)	0.0029 (8)	−0.0067 (7)	−0.0191 (8)
C11	0.0539 (12)	0.0828 (16)	0.0563 (12)	0.0192 (11)	−0.0175 (10)	−0.0339 (12)
C12	0.0585 (13)	0.0902 (17)	0.0528 (12)	0.0071 (11)	−0.0219 (10)	−0.0316 (12)
C13	0.0610 (12)	0.0576 (11)	0.0377 (9)	−0.0082 (9)	−0.0052 (8)	−0.0188 (8)
C14	0.0571 (12)	0.0483 (10)	0.0467 (10)	0.0026 (8)	−0.0046 (8)	−0.0193 (8)
C15	0.0497 (10)	0.0504 (10)	0.0448 (9)	0.0039 (8)	−0.0128 (8)	−0.0178 (8)
C16	0.0465 (10)	0.0559 (11)	0.0435 (9)	0.0069 (8)	−0.0069 (8)	−0.0220 (8)
C17	0.0533 (12)	0.0645 (13)	0.0523 (11)	−0.0018 (9)	−0.0097 (9)	−0.0228 (10)
C18	0.0619 (14)	0.0636 (14)	0.0746 (15)	−0.0065 (11)	−0.0065 (12)	−0.0264 (12)
C19	0.0589 (14)	0.0568 (13)	0.0715 (15)	0.0013 (10)	−0.0035 (11)	−0.0066 (11)
C20	0.0667 (15)	0.0747 (16)	0.0546 (12)	0.0087 (12)	−0.0160 (11)	−0.0115 (11)
C21	0.0588 (13)	0.0673 (13)	0.0506 (11)	0.0084 (10)	−0.0140 (9)	−0.0231 (10)

Geometric parameters (Å, º)

Br19—C19	1.903 (3)	C13—C14	1.376 (3)
O13A—N13	1.221 (3)	C14—C15	1.384 (3)
O13B—N13	1.208 (3)	C16—C17	1.396 (4)
N1—C2	1.388 (3)	C16—C21	1.398 (3)
N1—C8	1.394 (3)	C17—C18	1.381 (4)
N1—C10	1.425 (3)	C18—C19	1.374 (4)
N3—C2	1.314 (3)	C19—C20	1.377 (4)
N3—C9	1.378 (3)	C20—C21	1.371 (4)
N13—C13	1.468 (3)	C4—H4	0.9300
C2—C16	1.468 (3)	C5—H5	0.9300
C4—C5	1.368 (5)	C6—H6	0.9300
C4—C9	1.401 (4)	C7—H7	0.9300
C5—C6	1.388 (5)	C11—H11	0.9300
C6—C7	1.386 (4)	C12—H12	0.9300
C7—C8	1.387 (3)	C14—H14	0.9300
C8—C9	1.392 (3)	C15—H15	0.9300
C10—C11	1.383 (3)	C17—H17	0.9300
C10—C15	1.385 (3)	C18—H18	0.9300
C11—C12	1.375 (4)	C20—H20	0.9300
C12—C13	1.377 (4)	C21—H21	0.9300
C2—N1—C8	106.13 (17)	C17—C16—C21	118.1 (2)
C2—N1—C10	129.54 (18)	C16—C17—C18	120.7 (2)
C8—N1—C10	123.67 (17)	C17—C18—C19	119.1 (3)
C2—N3—C9	105.68 (18)	Br19—C19—C18	119.0 (2)
O13A—N13—O13B	123.6 (2)	Br19—C19—C20	119.1 (2)
O13A—N13—C13	117.9 (2)	C18—C19—C20	121.9 (3)
O13B—N13—C13	118.5 (2)	C19—C20—C21	118.6 (2)
N1—C2—N3	112.33 (19)	C16—C21—C20	121.6 (2)
N1—C2—C16	125.22 (19)	C5—C4—H4	121.00
N3—C2—C16	122.40 (18)	C9—C4—H4	121.00
C5—C4—C9	117.8 (3)	C4—C5—H5	119.00
C4—C5—C6	121.7 (3)	C6—C5—H5	119.00
C5—C6—C7	122.0 (3)	C5—C6—H6	119.00
C6—C7—C8	116.0 (2)	C7—C6—H6	119.00
N1—C8—C7	131.8 (2)	C6—C7—H7	122.00
N1—C8—C9	105.24 (18)	C8—C7—H7	122.00
C7—C8—C9	122.9 (2)	C10—C11—H11	120.00
N3—C9—C4	129.7 (2)	C12—C11—H11	120.00
N3—C9—C8	110.62 (19)	C11—C12—H12	121.00
C4—C9—C8	119.7 (2)	C13—C12—H12	121.00
N1—C10—C11	118.7 (2)	C13—C14—H14	121.00
N1—C10—C15	120.08 (19)	C15—C14—H14	121.00
C11—C10—C15	121.1 (2)	C10—C15—H15	120.00
C10—C11—C12	119.7 (2)	C14—C15—H15	120.00
C11—C12—C13	118.8 (2)	C16—C17—H17	120.00
N13—C13—C12	118.5 (2)	C18—C17—H17	120.00
N13—C13—C14	119.2 (2)	C17—C18—H18	120.00
C12—C13—C14	122.3 (2)	C19—C18—H18	120.00
C13—C14—C15	118.9 (2)	C19—C20—H20	121.00
C10—C15—C14	119.1 (2)	C21—C20—H20	121.00
C2—C16—C17	124.5 (2)	C16—C21—H21	119.00
C2—C16—C21	117.4 (2)	C20—C21—H21	119.00
C8—N1—C2—N3	0.0 (3)	C5—C6—C7—C8	0.5 (4)
C8—N1—C2—C16	177.3 (2)	C6—C7—C8—N1	−178.7 (3)
C10—N1—C2—N3	170.8 (2)	C6—C7—C8—C9	−0.4 (4)
C10—N1—C2—C16	−11.9 (4)	N1—C8—C9—N3	−0.6 (3)
C2—N1—C8—C7	178.8 (3)	N1—C8—C9—C4	178.9 (2)
C2—N1—C8—C9	0.3 (2)	C7—C8—C9—N3	−179.2 (2)
C10—N1—C8—C7	7.3 (4)	C7—C8—C9—C4	0.2 (4)
C10—N1—C8—C9	−171.2 (2)	N1—C10—C11—C12	177.9 (2)
C2—N1—C10—C11	123.1 (2)	C15—C10—C11—C12	0.4 (4)
C2—N1—C10—C15	−59.4 (3)	N1—C10—C15—C14	−178.47 (19)
C8—N1—C10—C11	−67.5 (3)	C11—C10—C15—C14	−1.0 (3)
C8—N1—C10—C15	110.0 (2)	C10—C11—C12—C13	0.2 (4)
C9—N3—C2—N1	−0.4 (3)	C11—C12—C13—N13	−179.3 (2)
C9—N3—C2—C16	−177.7 (2)	C11—C12—C13—C14	−0.3 (4)
C2—N3—C9—C4	−178.8 (3)	N13—C13—C14—C15	178.8 (2)
C2—N3—C9—C8	0.6 (3)	C12—C13—C14—C15	−0.3 (3)
O13A—N13—C13—C12	1.5 (3)	C13—C14—C15—C10	0.9 (3)
O13A—N13—C13—C14	−177.6 (2)	C2—C16—C17—C18	−177.3 (2)
O13B—N13—C13—C12	−179.3 (2)	C21—C16—C17—C18	−1.1 (4)
O13B—N13—C13—C14	1.6 (3)	C2—C16—C21—C20	177.1 (2)
N1—C2—C16—C17	−21.4 (4)	C17—C16—C21—C20	0.6 (4)
N1—C2—C16—C21	162.4 (2)	C16—C17—C18—C19	0.7 (4)
N3—C2—C16—C17	155.6 (2)	C17—C18—C19—Br19	−179.9 (2)
N3—C2—C16—C21	−20.6 (4)	C17—C18—C19—C20	0.2 (4)
C9—C4—C5—C6	0.2 (5)	Br19—C19—C20—C21	179.4 (2)
C5—C4—C9—N3	179.2 (3)	C18—C19—C20—C21	−0.7 (4)
C5—C4—C9—C8	−0.1 (4)	C19—C20—C21—C16	0.3 (4)
C4—C5—C6—C7	−0.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O13B^i	0.93	2.56	3.491 (4)	175
C12—H12···O13A^ii	0.93	2.51	3.312 (4)	145
C15—H15···N3^iii	0.93	2.56	3.463 (3)	165
C21—H21···N3	0.93	2.54	2.848 (4)	100

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