1-Butyl-3-(1-naphthyl-meth-yl)benzimidazolium hemi{di-μ-iodido-bis-[diiodidomercurate(II)]} dimethyl sulfoxide monosolvate.

In the title compound, (C(22)H(23)N(2))[Hg(2)I(6)](0.5)·(CH(3))(2)SO, the 1-butyl-3-(1-naphthyl-meth-yl)benzimidazolium anion lies across a centre of inversion. The dihedral angle between the benzimidazolium and naphthalene ring systems is 81.9 (3)°. In the crystal structure, π-π stacking inter-actions are observed between the imidazolium ring and the unsubstituted benzene ring of the naphthalene ring system, with a centroid-centroid separation of 3.510 (5) Å. In the centrosymmetric anion, the Hg(II) atoms are in a distorted tetrahedral coordination. The dimethyl sulfoxide solvent mol-ecule is disordered over two sites with occupancies of 0.615 (9) and 0.385 (9).

Related literature

For background to the chemistry of imidazolium compounds, see: Arduengo et al. (1991 ▶); Garrison & Youngs (2005 ▶). For a related structure, see: Liu et al. (2003 ▶).

Experimental

Crystal data

(C22H23N2)[Hg2I6]0.5·C2H6OS

M = 974.85

Monoclinic,

a = 12.0565 (13) Å

b = 13.7312 (16) Å

c = 18.378 (2) Å

β = 102.089 (2)°

V = 2975.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 8.38 mm−1

T = 296 K

0.28 × 0.26 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.110, T max = 0.158

14876 measured reflections

5253 independent reflections

3641 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.03

5253 reflections

327 parameters

60 restraints

H-atom parameters constrained

Δρmax = 1.16 e Å−3

Δρmin = −1.71 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536809046376/ci2946sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046376/ci2946Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C22H23N2)[Hg2I6]0.5·C2H6OS	F(000) = 1800
Mr = 974.85	Dx = 2.177 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3658 reflections
a = 12.0565 (13) Å	θ = 2.3–23.9°
b = 13.7312 (16) Å	µ = 8.38 mm−1
c = 18.378 (2) Å	T = 296 K
β = 102.089 (2)°	Block, yellow
V = 2975.0 (6) Å3	0.28 × 0.26 × 0.22 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5253 independent reflections
Radiation source: fine-focus sealed tube	3641 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.110, Tmax = 0.158	k = −16→11
14876 measured reflections	l = −21→21

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0474P)2 + 6.0193P] where P = (Fo2 + 2Fc2)/3
5253 reflections	(Δ/σ)max = 0.001
327 parameters	Δρmax = 1.16 e Å−3
60 restraints	Δρmin = −1.71 e Å−3

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	Occ. (<1)
Hg1	0.61164 (3)	0.57544 (3)	0.95810 (2)	0.07147 (16)
I1	0.83044 (5)	0.51958 (4)	0.98219 (4)	0.06220 (19)
I2	0.47338 (6)	0.40737 (6)	0.90484 (4)	0.0883 (3)
I3	0.53530 (6)	0.73713 (6)	0.88235 (5)	0.0985 (3)
N1	−0.0121 (6)	0.4144 (4)	0.2680 (3)	0.0446 (15)
N2	0.0684 (5)	0.3180 (4)	0.3578 (3)	0.0433 (15)
C1	−0.1740 (8)	0.6136 (6)	0.2289 (5)	0.059 (2)
H1	−0.2223	0.5783	0.1922	0.071*
C2	−0.2176 (9)	0.6929 (7)	0.2618 (6)	0.071 (3)
H2	−0.2938	0.7092	0.2468	0.085*
C3	−0.1503 (9)	0.7452 (7)	0.3148 (5)	0.065 (3)
H3	−0.1804	0.7969	0.3370	0.078*
C4	−0.0332 (8)	0.7225 (6)	0.3373 (4)	0.051 (2)
C5	0.0393 (9)	0.7759 (6)	0.3924 (5)	0.063 (2)
H5	0.0099	0.8269	0.4158	0.076*
C6	0.1503 (10)	0.7553 (7)	0.4125 (5)	0.071 (3)
H6	0.1966	0.7916	0.4495	0.085*
C7	0.1962 (9)	0.6798 (7)	0.3781 (5)	0.071 (3)
H7	0.2732	0.6658	0.3922	0.085*
C8	0.1289 (7)	0.6259 (6)	0.3235 (5)	0.057 (2)
H8	0.1614	0.5769	0.2999	0.068*
C9	0.0119 (7)	0.6431 (5)	0.3025 (4)	0.0476 (19)
C10	−0.0635 (7)	0.5867 (5)	0.2488 (4)	0.0460 (19)
C11	−0.0249 (7)	0.4955 (6)	0.2146 (4)	0.052 (2)
H11A	−0.0801	0.4782	0.1700	0.063*
H11B	0.0470	0.5078	0.2005	0.063*
C12	0.0855 (7)	0.3871 (5)	0.3116 (4)	0.0431 (18)
H12	0.1560	0.4131	0.3096	0.052*
C13	−0.0978 (6)	0.3588 (5)	0.2866 (4)	0.0412 (17)
C14	−0.2127 (8)	0.3544 (6)	0.2578 (5)	0.058 (2)
H14	−0.2478	0.3943	0.2189	0.069*
C15	−0.2726 (8)	0.2872 (8)	0.2901 (6)	0.069 (3)
H15	−0.3506	0.2823	0.2728	0.083*
C16	−0.2195 (9)	0.2262 (7)	0.3481 (6)	0.070 (3)
H16	−0.2632	0.1813	0.3677	0.084*
C17	−0.1077 (8)	0.2305 (6)	0.3763 (5)	0.057 (2)
H17	−0.0729	0.1902	0.4151	0.068*
C18	−0.0465 (7)	0.2981 (5)	0.3446 (4)	0.0445 (18)
C19	0.1555 (8)	0.2795 (6)	0.4189 (4)	0.058 (2)
H19A	0.2299	0.2893	0.4078	0.070*
H19B	0.1442	0.2101	0.4239	0.070*
C20	0.1505 (8)	0.3299 (6)	0.4918 (5)	0.059 (2)
H20A	0.0752	0.3207	0.5016	0.071*
H20B	0.2039	0.2981	0.5315	0.071*
C21	0.1762 (9)	0.4371 (7)	0.4943 (5)	0.072 (3)
H21A	0.2527	0.4460	0.4867	0.086*
H21B	0.1250	0.4684	0.4532	0.086*
C22	0.1665 (9)	0.4881 (8)	0.5648 (5)	0.084 (3)
H22A	0.0898	0.4837	0.5715	0.126*
H22B	0.1870	0.5553	0.5619	0.126*
H22C	0.2165	0.4579	0.6062	0.126*
S1	0.5566 (4)	0.8983 (4)	0.1687 (3)	0.0831 (19)	0.615 (9)
O1	0.6734 (8)	0.9226 (16)	0.1578 (11)	0.132 (10)	0.615 (9)
C23	0.5144 (19)	0.9966 (15)	0.2185 (12)	0.127 (11)	0.615 (9)
H23A	0.5567	0.9953	0.2689	0.191*	0.615 (9)
H23B	0.4349	0.9912	0.2181	0.191*	0.615 (9)
H23C	0.5285	1.0568	0.1954	0.191*	0.615 (9)
C24	0.4652 (16)	0.921 (2)	0.0812 (8)	0.160 (13)	0.615 (9)
H24A	0.4795	0.8736	0.0457	0.241*	0.615 (9)
H24B	0.4790	0.9850	0.0645	0.241*	0.615 (9)
H24C	0.3877	0.9157	0.0861	0.241*	0.615 (9)
S1'	0.5614 (7)	0.9773 (6)	0.1314 (4)	0.089 (3)	0.385 (9)
O1'	0.6753 (11)	0.943 (2)	0.1700 (14)	0.100 (11)	0.385 (9)
C23'	0.481 (2)	0.995 (2)	0.2005 (13)	0.077 (9)	0.385 (9)
H23D	0.5145	1.0455	0.2339	0.116*	0.385 (9)
H23E	0.4789	0.9355	0.2278	0.116*	0.385 (9)
H23F	0.4046	1.0133	0.1772	0.116*	0.385 (9)
C24'	0.485 (2)	0.8777 (19)	0.0855 (15)	0.112 (12)	0.385 (9)
H24D	0.5197	0.8569	0.0454	0.168*	0.385 (9)
H24E	0.4083	0.8968	0.0659	0.168*	0.385 (9)
H24F	0.4866	0.8250	0.1200	0.168*	0.385 (9)

	U11	U22	U33	U12	U13	U23
Hg1	0.0457 (2)	0.0806 (3)	0.0874 (3)	0.00266 (18)	0.01229 (19)	0.0094 (2)
I1	0.0479 (3)	0.0505 (3)	0.0878 (4)	0.0062 (3)	0.0134 (3)	−0.0007 (3)
I2	0.0773 (5)	0.1162 (6)	0.0770 (5)	−0.0384 (4)	0.0289 (4)	−0.0373 (4)
I3	0.0758 (5)	0.1001 (6)	0.1121 (6)	0.0222 (4)	0.0029 (4)	0.0270 (5)
N1	0.060 (4)	0.042 (4)	0.034 (3)	0.004 (3)	0.015 (3)	−0.001 (3)
N2	0.051 (4)	0.041 (3)	0.041 (4)	0.007 (3)	0.014 (3)	0.001 (3)
C1	0.075 (6)	0.050 (5)	0.053 (5)	0.005 (4)	0.013 (5)	0.016 (4)
C2	0.085 (7)	0.057 (6)	0.076 (7)	0.021 (5)	0.027 (6)	0.018 (5)
C3	0.099 (8)	0.047 (5)	0.060 (6)	0.015 (5)	0.039 (6)	0.002 (5)
C4	0.075 (6)	0.039 (4)	0.046 (5)	0.001 (4)	0.029 (4)	0.012 (4)
C5	0.091 (8)	0.048 (5)	0.059 (6)	−0.007 (5)	0.035 (5)	0.002 (4)
C6	0.108 (9)	0.053 (6)	0.057 (6)	−0.018 (6)	0.025 (6)	−0.002 (5)
C7	0.073 (6)	0.057 (6)	0.080 (7)	−0.015 (5)	0.012 (5)	0.009 (5)
C8	0.068 (6)	0.043 (5)	0.068 (6)	−0.002 (4)	0.036 (5)	0.010 (4)
C9	0.065 (5)	0.038 (4)	0.046 (5)	0.002 (4)	0.026 (4)	0.016 (4)
C10	0.070 (6)	0.043 (4)	0.028 (4)	0.008 (4)	0.014 (4)	0.009 (3)
C11	0.068 (5)	0.052 (5)	0.038 (4)	0.005 (4)	0.012 (4)	0.004 (4)
C12	0.047 (5)	0.044 (4)	0.038 (4)	0.000 (3)	0.009 (4)	−0.003 (4)
C13	0.046 (4)	0.042 (4)	0.039 (4)	0.003 (3)	0.016 (4)	−0.008 (4)
C14	0.069 (6)	0.055 (5)	0.050 (5)	0.009 (5)	0.014 (4)	−0.009 (4)
C15	0.047 (5)	0.086 (7)	0.075 (7)	−0.012 (5)	0.015 (5)	−0.027 (6)
C16	0.076 (7)	0.069 (6)	0.071 (6)	−0.017 (5)	0.029 (6)	−0.004 (5)
C17	0.071 (6)	0.055 (5)	0.049 (5)	−0.008 (4)	0.024 (5)	0.002 (4)
C18	0.057 (5)	0.042 (4)	0.038 (4)	0.003 (4)	0.017 (4)	−0.006 (4)
C19	0.064 (5)	0.053 (5)	0.056 (5)	0.006 (4)	0.008 (4)	0.007 (4)
C20	0.062 (5)	0.063 (6)	0.048 (5)	−0.004 (4)	0.002 (4)	0.010 (4)
C21	0.079 (7)	0.080 (7)	0.058 (6)	−0.003 (5)	0.018 (5)	0.004 (5)
C22	0.099 (8)	0.098 (8)	0.058 (6)	−0.015 (7)	0.022 (6)	−0.016 (6)
S1	0.078 (3)	0.085 (3)	0.094 (3)	0.016 (2)	0.036 (2)	0.019 (2)
O1	0.119 (11)	0.140 (11)	0.139 (11)	0.006 (5)	0.033 (5)	−0.008 (5)
C23	0.128 (12)	0.129 (12)	0.127 (12)	0.003 (5)	0.030 (5)	−0.004 (5)
C24	0.159 (13)	0.161 (13)	0.161 (13)	0.004 (5)	0.033 (6)	−0.001 (5)
S1'	0.093 (4)	0.086 (5)	0.098 (5)	0.007 (3)	0.043 (3)	0.009 (3)
O1'	0.090 (12)	0.107 (12)	0.108 (12)	0.004 (5)	0.028 (5)	−0.008 (5)
C23'	0.077 (10)	0.079 (10)	0.077 (10)	0.002 (5)	0.019 (5)	−0.004 (5)
C24'	0.110 (13)	0.111 (13)	0.114 (13)	0.002 (5)	0.024 (6)	−0.003 (5)

Hg1—I3	2.6792 (9)	C15—C16	1.402 (13)
Hg1—I1	2.6933 (7)	C15—H15	0.93
Hg1—I2	2.8943 (5)	C16—C17	1.341 (12)
Hg1—I2	2.8943 (4)	C16—H16	0.93
I2—Hg1	2.8943 (4)	C17—C18	1.387 (11)
N1—C12	1.331 (9)	C17—H17	0.93
N1—C13	1.384 (9)	C19—C20	1.519 (12)
N1—C11	1.472 (9)	C19—H19A	0.97
N2—C12	1.318 (9)	C19—H19B	0.97
N2—C18	1.383 (9)	C20—C21	1.503 (12)
N2—C19	1.466 (10)	C20—H20A	0.97
C1—C10	1.357 (11)	C20—H20B	0.97
C1—C2	1.400 (13)	C21—C22	1.498 (13)
C1—H1	0.93	C21—H21A	0.97
C2—C3	1.339 (13)	C21—H21B	0.97
C2—H2	0.93	C22—H22A	0.96
C3—C4	1.420 (13)	C22—H22B	0.96
C3—H3	0.93	C22—H22C	0.96
C4—C5	1.400 (12)	S1—O1	1.5010 (9)
C4—C9	1.428 (11)	S1—C23	1.7650 (9)
C5—C6	1.342 (14)	S1—C24	1.7750 (9)
C5—H5	0.93	C23—H23A	0.96
C6—C7	1.387 (14)	C23—H23B	0.96
C6—H6	0.93	C23—H23C	0.96
C7—C8	1.368 (12)	C24—H24A	0.96
C7—H7	0.93	C24—H24B	0.96
C8—C9	1.403 (11)	C24—H24C	0.96
C8—H8	0.93	S1'—O1'	1.484 (10)
C9—C10	1.423 (11)	S1'—C24'	1.761 (10)
C10—C11	1.518 (11)	S1'—C23'	1.771 (9)
C11—H11A	0.97	C23'—H23D	0.96
C11—H11B	0.97	C23'—H23E	0.96
C12—H12	0.9300	C23'—H23F	0.96
C13—C14	1.376 (11)	C24'—H24D	0.96
C13—C18	1.392 (10)	C24'—H24E	0.96
C14—C15	1.380 (13)	C24'—H24F	0.96
C14—H14	0.93
I3—Hg1—I1	122.65 (3)	C17—C16—H16	119.0
I3—Hg1—I2	111.97 (3)	C15—C16—H16	119.0
I1—Hg1—I2	107.66 (3)	C16—C17—C18	116.6 (9)
I3—Hg1—I2i	103.69 (3)	C16—C17—H17	121.7
I1—Hg1—I2i	112.94 (3)	C18—C17—H17	121.7
I2—Hg1—I2i	94.29 (2)	N2—C18—C17	131.3 (8)
Hg1—I2—Hg1i	85.71 (2)	N2—C18—C13	106.5 (6)
C12—N1—C13	108.0 (6)	C17—C18—C13	122.1 (8)
C12—N1—C11	124.8 (7)	N2—C19—C20	110.9 (7)
C13—N1—C11	127.1 (7)	N2—C19—H19A	109.5
C12—N2—C18	108.4 (6)	C20—C19—H19A	109.5
C12—N2—C19	124.8 (7)	N2—C19—H19B	109.5
C18—N2—C19	126.4 (7)	C20—C19—H19B	109.5
C10—C1—C2	122.1 (9)	H19A—C19—H19B	108.0
C10—C1—H1	118.9	C21—C20—C19	115.3 (8)
C2—C1—H1	118.9	C21—C20—H20A	108.4
C3—C2—C1	120.4 (9)	C19—C20—H20A	108.4
C3—C2—H2	119.8	C21—C20—H20B	108.4
C1—C2—H2	119.8	C19—C20—H20B	108.4
C2—C3—C4	120.6 (8)	H20A—C20—H20B	107.5
C2—C3—H3	119.7	C22—C21—C20	115.6 (9)
C4—C3—H3	119.7	C22—C21—H21A	108.4
C5—C4—C3	121.9 (8)	C20—C21—H21A	108.4
C5—C4—C9	119.0 (8)	C22—C21—H21B	108.4
C3—C4—C9	119.1 (8)	C20—C21—H21B	108.4
C6—C5—C4	121.6 (9)	H21A—C21—H21B	107.4
C6—C5—H5	119.2	C21—C22—H22A	109.5
C4—C5—H5	119.2	C21—C22—H22B	109.5
C5—C6—C7	120.1 (10)	H22A—C22—H22B	109.5
C5—C6—H6	119.9	C21—C22—H22C	109.5
C7—C6—H6	119.9	H22A—C22—H22C	109.5
C8—C7—C6	120.5 (10)	H22B—C22—H22C	109.5
C8—C7—H7	119.8	O1—S1—C23	106.2 (8)
C6—C7—H7	119.8	O1—S1—C24	105.2 (7)
C7—C8—C9	121.2 (9)	C23—S1—C24	98.3 (6)
C7—C8—H8	119.4	S1—C23—H23A	109.5
C9—C8—H8	119.4	S1—C23—H23B	109.5
C8—C9—C10	124.0 (7)	H23A—C23—H23B	109.5
C8—C9—C4	117.5 (8)	S1—C23—H23C	109.5
C10—C9—C4	118.6 (8)	H23A—C23—H23C	109.5
C1—C10—C9	119.2 (7)	H23B—C23—H23C	109.5
C1—C10—C11	118.8 (8)	S1—C24—H24A	109.5
C9—C10—C11	122.0 (7)	S1—C24—H24B	109.5
N1—C11—C10	110.3 (6)	H24A—C24—H24B	109.5
N1—C11—H11A	109.6	S1—C24—H24C	109.5
C10—C11—H11A	109.6	H24A—C24—H24C	109.5
N1—C11—H11B	109.6	H24B—C24—H24C	109.5
C10—C11—H11B	109.6	O1'—S1'—C24'	108.6 (8)
H11A—C11—H11B	108.1	O1'—S1'—C23'	107.1 (8)
N2—C12—N1	110.6 (7)	C24'—S1'—C23'	98.1 (7)
N2—C12—H12	124.7	S1'—C23'—H23D	109.5
N1—C12—H12	124.7	S1'—C23'—H23E	109.5
C14—C13—N1	132.3 (8)	H23D—C23'—H23E	109.5
C14—C13—C18	121.2 (8)	S1'—C23'—H23F	109.5
N1—C13—C18	106.5 (6)	H23D—C23'—H23F	109.5
C13—C14—C15	116.1 (8)	H23E—C23'—H23F	109.5
C13—C14—H14	122.0	S1'—C24'—H24D	109.5
C15—C14—H14	122.0	S1'—C24'—H24E	109.5
C14—C15—C16	122.0 (8)	H24D—C24'—H24E	109.5
C14—C15—H15	119.0	S1'—C24'—H24F	109.5
C16—C15—H15	119.0	H24D—C24'—H24F	109.5
C17—C16—C15	121.9 (9)	H24E—C24'—H24F	109.5
I3—Hg1—I2—Hg1i	−106.63 (3)	C18—N2—C12—N1	0.0 (8)
I1—Hg1—I2—Hg1i	115.73 (3)	C19—N2—C12—N1	−172.5 (6)
I2i—Hg1—I2—Hg1i	0.0	C13—N1—C12—N2	−0.7 (8)
C10—C1—C2—C3	0.0 (13)	C11—N1—C12—N2	174.5 (6)
C1—C2—C3—C4	1.3 (13)	C12—N1—C13—C14	−177.3 (8)
C2—C3—C4—C5	180.0 (8)	C11—N1—C13—C14	7.7 (12)
C2—C3—C4—C9	0.2 (12)	C12—N1—C13—C18	1.1 (8)
C3—C4—C5—C6	−178.7 (8)	C11—N1—C13—C18	−174.0 (6)
C9—C4—C5—C6	1.1 (12)	N1—C13—C14—C15	178.6 (7)
C4—C5—C6—C7	0.4 (13)	C18—C13—C14—C15	0.4 (11)
C5—C6—C7—C8	0.1 (14)	C13—C14—C15—C16	−0.8 (13)
C6—C7—C8—C9	−2.0 (13)	C14—C15—C16—C17	0.9 (14)
C7—C8—C9—C10	−176.8 (7)	C15—C16—C17—C18	−0.6 (13)
C7—C8—C9—C4	3.4 (11)	C12—N2—C18—C17	177.9 (8)
C5—C4—C9—C8	−2.9 (10)	C19—N2—C18—C17	−9.7 (13)
C3—C4—C9—C8	176.9 (7)	C12—N2—C18—C13	0.7 (8)
C5—C4—C9—C10	177.3 (7)	C19—N2—C18—C13	173.1 (7)
C3—C4—C9—C10	−2.9 (10)	C16—C17—C18—N2	−176.7 (8)
C2—C1—C10—C9	−2.8 (12)	C16—C17—C18—C13	0.1 (12)
C2—C1—C10—C11	175.5 (7)	C14—C13—C18—N2	177.5 (7)
C8—C9—C10—C1	−175.6 (7)	N1—C13—C18—N2	−1.1 (7)
C4—C9—C10—C1	4.2 (10)	C14—C13—C18—C17	−0.1 (11)
C8—C9—C10—C11	6.1 (11)	N1—C13—C18—C17	−178.7 (7)
C4—C9—C10—C11	−174.1 (6)	C12—N2—C19—C20	95.8 (9)
C12—N1—C11—C10	−97.1 (9)	C18—N2—C19—C20	−75.3 (9)
C13—N1—C11—C10	77.2 (9)	N2—C19—C20—C21	−63.9 (10)
C1—C10—C11—N1	−102.6 (8)	C19—C20—C21—C22	177.5 (8)
C9—C10—C11—N1	75.7 (9)