5-Chloro-1-nonyl-1H-benzimidazol-2(3H)-one.

The asymmetric unit of the title compound, C(16)H(23)ClN(2)O, comtains two independent mol-ecules in which the fused-ring systems are essentially planar, the largest deviation from the mean plane of each mol-ecule being 0.011 (2) Å and 0.016 (2) Å. The benzimidazole rings of the two mol-ecules make a dihedral angle of 66.65 (7)°. The nonyl substituents are almost perpendicular to the benzimidazole planes [C-N-C-C tosrsion angles = 96.0 (3) and 81.0 (2)°]. In the crystal, each independent molecule forms an inversion dimer via a pair of N-H⋯O hydrogen bonds. In one of the independent molecules, the terminal -CH(2)-CH(3) group of the alkyl chain is disordered over two sets of sites with a refined occupancy ratio of 0.746 (7):0.254 (7).

Related literature

For the pharmacological, biochemical and structural properties of benzimidazolo­nes, see: Al Muhaimeed (1997 ▶); Nakano et al. (2000 ▶); Scott et al. (2002 ▶); Zarrinmayeh et al. (1998 ▶); Zhu et al. (2000 ▶); Ouzidan et al. (2011a ▶,b ▶).

Experimental

Crystal data

C16H23ClN2O

M = 294.81

Triclinic,

a = 5.51441 (17) Å

b = 15.6507 (4) Å

c = 20.0540 (6) Å

α = 71.807 (3)°

β = 86.612 (2)°

γ = 80.709 (2)°

V = 1622.59 (8) Å3

Z = 4

Cu Kα radiation

μ = 2.06 mm−1

T = 296 K

0.43 × 0.20 × 0.16 mm

Data collection

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.640, T max = 0.720

31859 measured reflections

6416 independent reflections

5705 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.03

6416 reflections

379 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047829/im2336sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047829/im2336Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047829/im2336Isup3.cml

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

C16H23ClN2O	Z = 4
Mr = 294.81	F(000) = 632
Triclinic, P1	Dx = 1.207 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.51441 (17) Å	Cell parameters from 5000 reflections
b = 15.6507 (4) Å	θ = 5–50°
c = 20.0540 (6) Å	µ = 2.06 mm−1
α = 71.807 (3)°	T = 296 K
β = 86.612 (2)°	Block, yellow
γ = 80.709 (2)°	0.43 × 0.20 × 0.16 mm
V = 1622.59 (8) Å3

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer	6416 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	5705 reflections with I > 2σ(I)
mirror	Rint = 0.031
Detector resolution: 10.4051 pixels mm-1	θmax = 73.5°, θmin = 3.0°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −19→19
Tmin = 0.640, Tmax = 0.720	l = −24→24
31859 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.658P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
6416 reflections	Δρmax = 0.46 e Å−3
379 parameters	Δρmin = −0.32 e Å−3
9 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (3)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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)
Cl1	0.25688 (10)	1.14681 (4)	0.21378 (3)	0.05904 (16)
O1	0.9124 (2)	0.88615 (9)	0.54464 (7)	0.0510 (3)
N1	0.6002 (3)	0.87446 (10)	0.47672 (8)	0.0432 (3)
N2	0.7802 (3)	0.99710 (11)	0.44015 (8)	0.0434 (3)
H2	0.873 (4)	1.0339 (15)	0.4395 (11)	0.049 (6)*
C1	0.4881 (3)	0.92923 (12)	0.41404 (9)	0.0409 (4)
C2	0.6050 (3)	1.00686 (12)	0.39072 (9)	0.0400 (4)
C3	0.5395 (3)	1.07491 (12)	0.32944 (9)	0.0434 (4)
H3	0.6185	1.1259	0.3135	0.052*
C4	0.3486 (3)	1.06323 (13)	0.29259 (9)	0.0441 (4)
C5	0.2297 (3)	0.98786 (14)	0.31460 (10)	0.0469 (4)
H5	0.1026	0.9832	0.2881	0.056*
C6	0.2996 (3)	0.91879 (13)	0.37635 (10)	0.0463 (4)
H6	0.2220	0.8674	0.3917	0.056*
C7	0.7793 (3)	0.91679 (13)	0.49246 (9)	0.0430 (4)
C11	0.5279 (4)	0.79200 (14)	0.52610 (10)	0.0521 (5)
H11A	0.3529	0.7936	0.5218	0.063*
H11B	0.5576	0.7914	0.5734	0.063*
C12	0.6626 (4)	0.70491 (14)	0.51532 (11)	0.0555 (5)
H12A	0.8369	0.7087	0.5110	0.067*
H12B	0.6391	0.6548	0.5570	0.067*
C13	0.5848 (4)	0.68309 (13)	0.45206 (11)	0.0526 (5)
H13A	0.6122	0.7321	0.4100	0.063*
H13B	0.4102	0.6797	0.4557	0.063*
C14	0.7238 (4)	0.59384 (14)	0.44517 (12)	0.0573 (5)
H14A	0.8975	0.5986	0.4395	0.069*
H14B	0.7032	0.5457	0.4884	0.069*
C15	0.6427 (4)	0.56742 (13)	0.38457 (12)	0.0578 (5)
H15A	0.6546	0.6168	0.3415	0.069*
H15B	0.4716	0.5589	0.3916	0.069*
C16	0.7941 (5)	0.48115 (16)	0.37656 (15)	0.0746 (7)
H16A	0.9640	0.4908	0.3680	0.090*
H16B	0.7876	0.4326	0.4205	0.090*
C17	0.7129 (7)	0.4510 (2)	0.31899 (18)	0.0965 (10)
H17A	0.7396	0.4950	0.2739	0.116*	0.746 (7)
H17B	0.5388	0.4469	0.3241	0.116*	0.746 (7)
H17C	0.6367	0.5062	0.2847	0.116*	0.254 (7)
H17D	0.5809	0.4166	0.3392	0.116*	0.254 (7)
C18	0.8622 (12)	0.3558 (3)	0.3220 (2)	0.118 (2)	0.746 (7)
H18A	1.0352	0.3620	0.3170	0.141*	0.746 (7)
H18B	0.8392	0.3142	0.3684	0.141*	0.746 (7)
C19	0.8116 (13)	0.3189 (4)	0.2768 (4)	0.167 (3)	0.746 (7)
H19A	0.9265	0.2645	0.2810	0.250*	0.746 (7)
H19B	0.8222	0.3606	0.2304	0.250*	0.746 (7)
H19C	0.6481	0.3040	0.2853	0.250*	0.746 (7)
C18'	0.869 (2)	0.3959 (10)	0.2756 (8)	0.095 (4)*	0.254 (7)
H18C	0.7580	0.3612	0.2632	0.115*	0.254 (7)
H18D	0.9086	0.4405	0.2321	0.115*	0.254 (7)
C19'	1.056 (2)	0.3440 (8)	0.2934 (7)	0.084 (4)*	0.254 (7)
H19D	1.1224	0.3233	0.2548	0.126*	0.254 (7)
H19E	1.0224	0.2929	0.3321	0.126*	0.254 (7)
H19F	1.1727	0.3744	0.3073	0.126*	0.254 (7)
Cl1A	1.08169 (10)	−0.26825 (3)	0.31097 (3)	0.06033 (16)
O1A	1.2494 (2)	0.09656 (8)	−0.01986 (6)	0.0430 (3)
N1A	0.9635 (2)	0.06117 (9)	0.07076 (7)	0.0368 (3)
N2A	1.3088 (2)	−0.03410 (9)	0.07700 (7)	0.0367 (3)
H2A	1.445 (4)	−0.0579 (13)	0.0637 (10)	0.042 (5)*
C1A	0.9508 (3)	−0.01099 (11)	0.13176 (9)	0.0347 (3)
C2A	1.1701 (3)	−0.07145 (11)	0.13562 (9)	0.0345 (3)
C3A	1.2157 (3)	−0.15133 (11)	0.18992 (9)	0.0386 (4)
H3A	1.3617	−0.1914	0.1927	0.046*
C4A	1.0307 (3)	−0.16868 (12)	0.24037 (9)	0.0414 (4)
C5A	0.8119 (3)	−0.11037 (13)	0.23750 (9)	0.0425 (4)
H5A	0.6934	−0.1251	0.2724	0.051*
C6A	0.7689 (3)	−0.02980 (12)	0.18245 (9)	0.0395 (4)
H6A	0.6228	0.0102	0.1798	0.047*
C7A	1.1823 (3)	0.04634 (11)	0.03651 (9)	0.0358 (3)
C11A	0.7749 (3)	0.13966 (11)	0.04375 (9)	0.0394 (4)
H11C	0.6153	0.1195	0.0505	0.047*
H11D	0.8009	0.1657	−0.0063	0.047*
C12A	0.7736 (3)	0.21293 (11)	0.07887 (10)	0.0403 (4)
H12C	0.9238	0.2394	0.0667	0.048*
H12D	0.7690	0.1857	0.1294	0.048*
C13A	0.5537 (3)	0.28753 (11)	0.05638 (10)	0.0416 (4)
H13C	0.4042	0.2603	0.0661	0.050*
H13D	0.5634	0.3166	0.0061	0.050*
C14A	0.5394 (3)	0.35946 (12)	0.09357 (11)	0.0477 (4)
H14C	0.5532	0.3293	0.1437	0.057*
H14D	0.6785	0.3920	0.0788	0.057*
C15A	0.3046 (3)	0.42779 (12)	0.07968 (11)	0.0486 (4)
H15C	0.1654	0.3954	0.0950	0.058*
H15D	0.2899	0.4577	0.0295	0.058*
C16A	0.2936 (4)	0.49973 (13)	0.11649 (12)	0.0521 (5)
H16C	0.4253	0.5352	0.0984	0.062*
H16D	0.3220	0.4696	0.1662	0.062*
C17A	0.0511 (4)	0.56397 (13)	0.10765 (12)	0.0513 (5)
H17E	0.0253	0.5955	0.0581	0.062*
H17F	−0.0811	0.5283	0.1244	0.062*
C18A	0.0374 (4)	0.63392 (15)	0.14628 (14)	0.0618 (6)
H18E	0.0751	0.6027	0.1953	0.074*
H18F	0.1612	0.6728	0.1271	0.074*
C19A	−0.2113 (4)	0.69262 (15)	0.14139 (15)	0.0666 (6)
H19G	−0.2089	0.7353	0.1668	0.100*
H19H	−0.3346	0.6548	0.1613	0.100*
H19I	−0.2483	0.7250	0.0930	0.100*

	U11	U22	U33	U12	U13	U23
Cl1	0.0582 (3)	0.0627 (3)	0.0485 (3)	0.0098 (2)	−0.0121 (2)	−0.0134 (2)
O1	0.0467 (7)	0.0585 (8)	0.0468 (7)	−0.0017 (6)	−0.0114 (6)	−0.0160 (6)
N1	0.0388 (8)	0.0488 (8)	0.0421 (8)	−0.0026 (6)	−0.0022 (6)	−0.0155 (6)
N2	0.0385 (8)	0.0489 (8)	0.0446 (8)	−0.0044 (7)	−0.0046 (6)	−0.0173 (7)
C1	0.0345 (8)	0.0476 (9)	0.0414 (9)	0.0018 (7)	0.0004 (7)	−0.0191 (7)
C2	0.0326 (8)	0.0486 (9)	0.0417 (9)	0.0009 (7)	−0.0006 (7)	−0.0216 (7)
C3	0.0403 (9)	0.0458 (9)	0.0444 (9)	0.0003 (7)	0.0009 (7)	−0.0180 (8)
C4	0.0389 (9)	0.0520 (10)	0.0409 (9)	0.0072 (7)	−0.0030 (7)	−0.0199 (8)
C5	0.0350 (9)	0.0607 (11)	0.0495 (10)	0.0022 (8)	−0.0059 (7)	−0.0269 (9)
C6	0.0378 (9)	0.0531 (10)	0.0513 (10)	−0.0031 (8)	−0.0009 (8)	−0.0225 (8)
C7	0.0361 (9)	0.0513 (10)	0.0429 (9)	0.0024 (7)	−0.0026 (7)	−0.0202 (8)
C11	0.0491 (11)	0.0587 (11)	0.0450 (10)	−0.0084 (9)	0.0010 (8)	−0.0111 (9)
C12	0.0517 (11)	0.0519 (11)	0.0547 (11)	−0.0041 (9)	−0.0080 (9)	−0.0050 (9)
C13	0.0498 (11)	0.0475 (10)	0.0527 (11)	−0.0016 (8)	−0.0024 (9)	−0.0068 (8)
C14	0.0552 (12)	0.0441 (10)	0.0616 (12)	−0.0007 (9)	−0.0009 (10)	−0.0037 (9)
C15	0.0588 (12)	0.0414 (10)	0.0664 (13)	−0.0022 (9)	0.0010 (10)	−0.0098 (9)
C16	0.0811 (17)	0.0474 (12)	0.0872 (17)	0.0025 (11)	0.0077 (14)	−0.0166 (12)
C17	0.119 (3)	0.0678 (17)	0.111 (2)	−0.0117 (16)	0.022 (2)	−0.0447 (17)
C18	0.199 (6)	0.065 (2)	0.074 (3)	0.010 (3)	0.041 (3)	−0.023 (2)
C19	0.153 (6)	0.113 (5)	0.272 (9)	−0.012 (4)	0.016 (6)	−0.119 (6)
Cl1A	0.0607 (3)	0.0530 (3)	0.0560 (3)	−0.0081 (2)	0.0013 (2)	−0.0012 (2)
O1A	0.0374 (6)	0.0425 (6)	0.0453 (7)	−0.0005 (5)	0.0027 (5)	−0.0113 (5)
N1A	0.0302 (7)	0.0375 (7)	0.0436 (7)	0.0013 (5)	−0.0006 (6)	−0.0170 (6)
N2A	0.0275 (7)	0.0388 (7)	0.0432 (8)	0.0019 (5)	0.0023 (6)	−0.0156 (6)
C1A	0.0293 (8)	0.0379 (8)	0.0411 (8)	−0.0019 (6)	−0.0028 (6)	−0.0193 (7)
C2A	0.0279 (7)	0.0385 (8)	0.0415 (8)	−0.0033 (6)	−0.0005 (6)	−0.0195 (7)
C3A	0.0311 (8)	0.0373 (8)	0.0486 (9)	−0.0009 (6)	−0.0024 (7)	−0.0169 (7)
C4A	0.0403 (9)	0.0410 (9)	0.0438 (9)	−0.0081 (7)	−0.0021 (7)	−0.0131 (7)
C5A	0.0347 (9)	0.0524 (10)	0.0443 (9)	−0.0101 (7)	0.0051 (7)	−0.0196 (8)
C6A	0.0277 (8)	0.0484 (9)	0.0462 (9)	−0.0004 (7)	0.0000 (7)	−0.0229 (8)
C7A	0.0307 (8)	0.0373 (8)	0.0428 (9)	−0.0025 (6)	−0.0016 (7)	−0.0180 (7)
C11A	0.0311 (8)	0.0411 (9)	0.0470 (9)	0.0034 (6)	−0.0060 (7)	−0.0182 (7)
C12A	0.0327 (8)	0.0385 (8)	0.0512 (10)	0.0006 (6)	−0.0060 (7)	−0.0180 (7)
C13A	0.0365 (9)	0.0385 (9)	0.0480 (10)	0.0032 (7)	−0.0047 (7)	−0.0146 (7)
C14A	0.0437 (10)	0.0408 (9)	0.0598 (11)	0.0029 (7)	−0.0064 (8)	−0.0206 (8)
C15A	0.0428 (10)	0.0432 (9)	0.0617 (12)	0.0037 (8)	−0.0047 (8)	−0.0229 (9)
C16A	0.0442 (10)	0.0466 (10)	0.0686 (13)	0.0046 (8)	−0.0058 (9)	−0.0270 (9)
C17A	0.0435 (10)	0.0449 (10)	0.0684 (13)	0.0037 (8)	−0.0053 (9)	−0.0260 (9)
C18A	0.0461 (11)	0.0578 (12)	0.0918 (16)	0.0046 (9)	−0.0058 (10)	−0.0428 (12)
C19A	0.0532 (12)	0.0552 (12)	0.1005 (18)	0.0067 (9)	−0.0053 (12)	−0.0434 (13)

Cl1—C4	1.7478 (19)	C18'—H18D	0.9700
O1—C7	1.236 (2)	C19'—H19D	0.9600
N1—C7	1.376 (2)	C19'—H19E	0.9600
N1—C1	1.395 (2)	C19'—H19F	0.9600
N1—C11	1.458 (2)	Cl1A—C4A	1.7435 (18)
N2—C7	1.363 (2)	O1A—C7A	1.234 (2)
N2—C2	1.382 (2)	N1A—C7A	1.376 (2)
N2—H2	0.83 (2)	N1A—C1A	1.389 (2)
C1—C6	1.379 (3)	N1A—C11A	1.457 (2)
C1—C2	1.405 (3)	N2A—C7A	1.370 (2)
C2—C3	1.373 (3)	N2A—C2A	1.385 (2)
C3—C4	1.388 (3)	N2A—H2A	0.85 (2)
C3—H3	0.9300	C1A—C6A	1.383 (2)
C4—C5	1.381 (3)	C1A—C2A	1.400 (2)
C5—C6	1.392 (3)	C2A—C3A	1.376 (2)
C5—H5	0.9300	C3A—C4A	1.391 (2)
C6—H6	0.9300	C3A—H3A	0.9300
C11—C12	1.515 (3)	C4A—C5A	1.383 (2)
C11—H11A	0.9700	C5A—C6A	1.389 (3)
C11—H11B	0.9700	C5A—H5A	0.9300
C12—C13	1.514 (3)	C6A—H6A	0.9300
C12—H12A	0.9700	C11A—C12A	1.521 (2)
C12—H12B	0.9700	C11A—H11C	0.9700
C13—C14	1.523 (3)	C11A—H11D	0.9700
C13—H13A	0.9700	C12A—C13A	1.522 (2)
C13—H13B	0.9700	C12A—H12C	0.9700
C14—C15	1.512 (3)	C12A—H12D	0.9700
C14—H14A	0.9700	C13A—C14A	1.523 (2)
C14—H14B	0.9700	C13A—H13C	0.9700
C15—C16	1.517 (3)	C13A—H13D	0.9700
C15—H15A	0.9700	C14A—C15A	1.519 (2)
C15—H15B	0.9700	C14A—H14C	0.9700
C16—C17	1.492 (4)	C14A—H14D	0.9700
C16—H16A	0.9700	C15A—C16A	1.519 (3)
C16—H16B	0.9700	C15A—H15C	0.9700
C17—C18'	1.543 (11)	C15A—H15D	0.9700
C17—C18	1.566 (5)	C16A—C17A	1.521 (2)
C17—H17A	0.9700	C16A—H16C	0.9700
C17—H17B	0.9700	C16A—H16D	0.9700
C17—H17C	0.9700	C17A—C18A	1.517 (3)
C17—H17D	0.9700	C17A—H17E	0.9700
C18—C19	1.282 (7)	C17A—H17F	0.9700
C18—H18A	0.9700	C18A—C19A	1.512 (3)
C18—H18B	0.9700	C18A—H18E	0.9700
C19—H19A	0.9600	C18A—H18F	0.9700
C19—H19B	0.9600	C19A—H19G	0.9600
C19—H19C	0.9600	C19A—H19H	0.9600
C18'—C19'	1.202 (12)	C19A—H19I	0.9600
C18'—H18C	0.9700
C7—N1—C1	109.15 (15)	H19B—C19—H19C	109.5
C7—N1—C11	121.78 (16)	C19'—C18'—C17	126.9 (12)
C1—N1—C11	128.50 (16)	C19'—C18'—H18C	105.6
C7—N2—C2	110.23 (16)	C17—C18'—H18C	105.6
C7—N2—H2	123.3 (15)	C19'—C18'—H18D	105.6
C2—N2—H2	126.5 (15)	C17—C18'—H18D	105.6
C6—C1—N1	132.18 (18)	H18C—C18'—H18D	106.1
C6—C1—C2	121.04 (17)	C18'—C19'—H19D	109.5
N1—C1—C2	106.78 (15)	C18'—C19'—H19E	109.5
C3—C2—N2	131.50 (17)	H19D—C19'—H19E	109.5
C3—C2—C1	121.83 (16)	C18'—C19'—H19F	109.5
N2—C2—C1	106.67 (16)	H19D—C19'—H19F	109.5
C2—C3—C4	116.14 (17)	H19E—C19'—H19F	109.5
C2—C3—H3	121.9	C7A—N1A—C1A	109.46 (13)
C4—C3—H3	121.9	C7A—N1A—C11A	123.64 (14)
C5—C4—C3	123.14 (17)	C1A—N1A—C11A	126.86 (13)
C5—C4—Cl1	118.22 (14)	C7A—N2A—C2A	109.97 (13)
C3—C4—Cl1	118.63 (15)	C7A—N2A—H2A	122.0 (13)
C4—C5—C6	120.23 (17)	C2A—N2A—H2A	127.7 (13)
C4—C5—H5	119.9	C6A—C1A—N1A	131.97 (15)
C6—C5—H5	119.9	C6A—C1A—C2A	121.06 (15)
C1—C6—C5	117.62 (18)	N1A—C1A—C2A	106.96 (13)
C1—C6—H6	121.2	C3A—C2A—N2A	131.38 (14)
C5—C6—H6	121.2	C3A—C2A—C1A	121.85 (15)
O1—C7—N2	127.51 (18)	N2A—C2A—C1A	106.77 (14)
O1—C7—N1	125.34 (18)	C2A—C3A—C4A	116.09 (15)
N2—C7—N1	107.16 (15)	C2A—C3A—H3A	122.0
N1—C11—C12	113.94 (16)	C4A—C3A—H3A	122.0
N1—C11—H11A	108.8	C5A—C4A—C3A	123.16 (16)
C12—C11—H11A	108.8	C5A—C4A—Cl1A	118.98 (14)
N1—C11—H11B	108.8	C3A—C4A—Cl1A	117.85 (13)
C12—C11—H11B	108.8	C4A—C5A—C6A	120.05 (16)
H11A—C11—H11B	107.7	C4A—C5A—H5A	120.0
C13—C12—C11	115.51 (17)	C6A—C5A—H5A	120.0
C13—C12—H12A	108.4	C1A—C6A—C5A	117.78 (15)
C11—C12—H12A	108.4	C1A—C6A—H6A	121.1
C13—C12—H12B	108.4	C5A—C6A—H6A	121.1
C11—C12—H12B	108.4	O1A—C7A—N2A	127.19 (15)
H12A—C12—H12B	107.5	O1A—C7A—N1A	125.98 (15)
C12—C13—C14	112.76 (17)	N2A—C7A—N1A	106.83 (14)
C12—C13—H13A	109.0	N1A—C11A—C12A	113.23 (14)
C14—C13—H13A	109.0	N1A—C11A—H11C	108.9
C12—C13—H13B	109.0	C12A—C11A—H11C	108.9
C14—C13—H13B	109.0	N1A—C11A—H11D	108.9
H13A—C13—H13B	107.8	C12A—C11A—H11D	108.9
C15—C14—C13	114.34 (17)	H11C—C11A—H11D	107.7
C15—C14—H14A	108.7	C11A—C12A—C13A	111.52 (14)
C13—C14—H14A	108.7	C11A—C12A—H12C	109.3
C15—C14—H14B	108.7	C13A—C12A—H12C	109.3
C13—C14—H14B	108.7	C11A—C12A—H12D	109.3
H14A—C14—H14B	107.6	C13A—C12A—H12D	109.3
C14—C15—C16	113.1 (2)	H12C—C12A—H12D	108.0
C14—C15—H15A	109.0	C12A—C13A—C14A	112.85 (15)
C16—C15—H15A	109.0	C12A—C13A—H13C	109.0
C14—C15—H15B	109.0	C14A—C13A—H13C	109.0
C16—C15—H15B	109.0	C12A—C13A—H13D	109.0
H15A—C15—H15B	107.8	C14A—C13A—H13D	109.0
C17—C16—C15	114.6 (2)	H13C—C13A—H13D	107.8
C17—C16—H16A	108.6	C15A—C14A—C13A	114.10 (16)
C15—C16—H16A	108.6	C15A—C14A—H14C	108.7
C17—C16—H16B	108.6	C13A—C14A—H14C	108.7
C15—C16—H16B	108.6	C15A—C14A—H14D	108.7
H16A—C16—H16B	107.6	C13A—C14A—H14D	108.7
C16—C17—C18'	128.3 (6)	H14C—C14A—H14D	107.6
C16—C17—C18	109.5 (3)	C14A—C15A—C16A	113.61 (16)
C18'—C17—C18	35.5 (5)	C14A—C15A—H15C	108.8
C16—C17—H17A	109.8	C16A—C15A—H15C	108.8
C18'—C17—H17A	74.6	C14A—C15A—H15D	108.8
C18—C17—H17A	109.8	C16A—C15A—H15D	108.8
C16—C17—H17B	109.8	H15C—C15A—H15D	107.7
C18'—C17—H17B	117.5	C15A—C16A—C17A	114.03 (16)
C18—C17—H17B	109.8	C15A—C16A—H16C	108.7
H17A—C17—H17B	108.2	C17A—C16A—H16C	108.7
C16—C17—H17C	105.2	C15A—C16A—H16D	108.7
C18'—C17—H17C	105.2	C17A—C16A—H16D	108.7
C18—C17—H17C	139.6	H16C—C16A—H16D	107.6
H17A—C17—H17C	36.9	C18A—C17A—C16A	114.01 (17)
H17B—C17—H17C	76.1	C18A—C17A—H17E	108.8
C16—C17—H17D	105.2	C16A—C17A—H17E	108.8
C18'—C17—H17D	105.2	C18A—C17A—H17F	108.8
C18—C17—H17D	84.3	C16A—C17A—H17F	108.8
H17A—C17—H17D	134.3	H17E—C17A—H17F	107.6
H17B—C17—H17D	30.1	C19A—C18A—C17A	113.28 (18)
H17C—C17—H17D	105.9	C19A—C18A—H18E	108.9
C19—C18—C17	117.6 (5)	C17A—C18A—H18E	108.9
C19—C18—H18A	107.9	C19A—C18A—H18F	108.9
C17—C18—H18A	107.9	C17A—C18A—H18F	108.9
C19—C18—H18B	107.9	H18E—C18A—H18F	107.7
C17—C18—H18B	107.9	C18A—C19A—H19G	109.5
H18A—C18—H18B	107.2	C18A—C19A—H19H	109.5
C18—C19—H19A	109.5	H19G—C19A—H19H	109.5
C18—C19—H19B	109.5	C18A—C19A—H19I	109.5
H19A—C19—H19B	109.5	H19G—C19A—H19I	109.5
C18—C19—H19C	109.5	H19H—C19A—H19I	109.5
H19A—C19—H19C	109.5
C7—N1—C1—C6	−179.22 (18)	C16—C17—C18'—C19'	26 (2)
C11—N1—C1—C6	−7.9 (3)	C18—C17—C18'—C19'	−42.3 (13)
C7—N1—C1—C2	0.62 (18)	C7A—N1A—C1A—C6A	−177.64 (17)
C11—N1—C1—C2	171.91 (16)	C11A—N1A—C1A—C6A	−0.1 (3)
C7—N2—C2—C3	−179.52 (17)	C7A—N1A—C1A—C2A	0.82 (18)
C7—N2—C2—C1	0.68 (18)	C11A—N1A—C1A—C2A	178.39 (14)
C6—C1—C2—C3	−0.7 (3)	C7A—N2A—C2A—C3A	178.36 (17)
N1—C1—C2—C3	179.40 (14)	C7A—N2A—C2A—C1A	−0.95 (18)
C6—C1—C2—N2	179.08 (15)	C6A—C1A—C2A—C3A	−0.6 (2)
N1—C1—C2—N2	−0.78 (18)	N1A—C1A—C2A—C3A	−179.32 (14)
N2—C2—C3—C4	−178.71 (17)	C6A—C1A—C2A—N2A	178.74 (15)
C1—C2—C3—C4	1.1 (2)	N1A—C1A—C2A—N2A	0.07 (17)
C2—C3—C4—C5	−0.7 (2)	N2A—C2A—C3A—C4A	−178.81 (16)
C2—C3—C4—Cl1	−179.55 (12)	C1A—C2A—C3A—C4A	0.4 (2)
C3—C4—C5—C6	−0.1 (3)	C2A—C3A—C4A—C5A	0.0 (3)
Cl1—C4—C5—C6	178.81 (13)	C2A—C3A—C4A—Cl1A	−179.05 (12)
N1—C1—C6—C5	179.77 (17)	C3A—C4A—C5A—C6A	−0.3 (3)
C2—C1—C6—C5	0.0 (2)	Cl1A—C4A—C5A—C6A	178.81 (13)
C4—C5—C6—C1	0.4 (3)	N1A—C1A—C6A—C5A	178.69 (16)
C2—N2—C7—O1	179.57 (17)	C2A—C1A—C6A—C5A	0.4 (2)
C2—N2—C7—N1	−0.30 (19)	C4A—C5A—C6A—C1A	0.0 (3)
C1—N1—C7—O1	179.92 (16)	C2A—N2A—C7A—O1A	−178.60 (16)
C11—N1—C7—O1	7.9 (3)	C2A—N2A—C7A—N1A	1.45 (18)
C1—N1—C7—N2	−0.20 (18)	C1A—N1A—C7A—O1A	178.65 (15)
C11—N1—C7—N2	−172.19 (15)	C11A—N1A—C7A—O1A	1.0 (3)
C7—N1—C11—C12	−93.8 (2)	C1A—N1A—C7A—N2A	−1.40 (18)
C1—N1—C11—C12	95.8 (2)	C11A—N1A—C7A—N2A	−179.06 (14)
N1—C11—C12—C13	−73.8 (2)	C7A—N1A—C11A—C12A	−101.69 (18)
C11—C12—C13—C14	−178.88 (17)	C1A—N1A—C11A—C12A	81.1 (2)
C12—C13—C14—C15	177.21 (18)	N1A—C11A—C12A—C13A	−172.36 (14)
C13—C14—C15—C16	176.70 (19)	C11A—C12A—C13A—C14A	176.96 (15)
C14—C15—C16—C17	177.7 (2)	C12A—C13A—C14A—C15A	−172.27 (16)
C15—C16—C17—C18'	151.9 (8)	C13A—C14A—C15A—C16A	−179.44 (17)
C15—C16—C17—C18	−173.2 (3)	C14A—C15A—C16A—C17A	−175.42 (18)
C16—C17—C18—C19	178.6 (6)	C15A—C16A—C17A—C18A	178.20 (19)
C18'—C17—C18—C19	−51.9 (10)	C16A—C17A—C18A—C19A	−175.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.83 (2)	1.96 (2)	2.778 (2)	170 (2)
N2A—H2A···O1Aii	0.85 (2)	1.95 (2)	2.7937 (18)	171.1 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.83 (2)	1.96 (2)	2.778 (2)	170 (2)
N2A—H2A⋯O1Aii	0.85 (2)	1.95 (2)	2.7937 (18)	171.1 (19)

Symmetry codes: (i) ; (ii) .