4-Chloro-N-(2,6-dichloro-phen-yl)benzamide.

The title compound, C(13)H(8)Cl(3)NO, crystallizes with four mol-ecules in the asymmetric unit. In the mol-ecular structure, the conformations of the central amide -CONH group show a wide range of dihedral angles with respect to the attached aromatic rings (benzoyl and anilino). The dihedral angles between the amide group and the benzoyl ring are 8.1 (3), 4.3 (3), 27.8 (1) and 32.7 (2)° in the four mol-ecules. The amide group is twisted out of the plane of the anilino ring, as shown by the dihedral angles of 85.4 (1), 74.3 (1), 88.1 (1) and 77.6 (1)° in the four mol-ecules. The aromatic rings are oriented at dihedral angles of 86.6 (1), 78.0 (1), 60.3 (1) and 69.8 (1)° in the four mol-ecules. The crystal structure is stabilized via inter-molecular N-H⋯O hydrogen bonds, aromatic aromatic inter-actions, short Cl⋯Cl contacts and C-H⋯Cl hydrogen bonds. Inter-molecular hydrogen bonds connect the mol-ecules into two distinct chains running along the c axis of the crystal. One mol-ecule forms an inversion dimer in which the main inter-actions are π-π stacking [centroid-centroid distances = 3.749 (1) and 3.760 (1) Å] and a short Cl⋯Cl contact of 3.408 (1) Å.

Related literature

For the biological activity of benzamide and benzanilide derivatives, see: Glaser (2007 ▶); Pasha et al. (2008 ▶); Brunhofer et al. (2008 ▶); Calderone et al. (2006 ▶); Stauffer et al. (2000 ▶); Lindgren et al. (2001 ▶). For anion recognition, see: Kang et al. (2006 ▶); Sun et al. (2009 ▶). For theoretical study of inter­nal rotations, see: Nishikawa et al. (2005 ▶). For related structures, see: Bowes et al. (2003 ▶); Gowda et al. (2003 ▶); Saeed et al. (2008 ▶).

Experimental

Crystal data

C13H8Cl3NO

M = 300.55

Monoclinic,

a = 16.9411 (3) Å

b = 16.3246 (2) Å

c = 19.5505 (3) Å

β = 95.3678 (13)°

V = 5383.11 (14) Å3

Z = 16

Mo Kα radiation

μ = 0.67 mm−1

T = 295 K

0.51 × 0.11 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2008 ▶), based on Clark & Reid (1995 ▶)] T min = 0.754, T max = 0.944

180094 measured reflections

10264 independent reflections

5984 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 0.98

10278 reflections

670 parameters

15 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902265X/zl2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902265X/zl2218Isup2.hkl

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

C13H8Cl3NO	F(000) = 2432
Mr = 300.55	Dx = 1.483 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 40513 reflections
a = 16.9411 (3) Å	θ = 3.0–29.6°
b = 16.3246 (2) Å	µ = 0.67 mm−1
c = 19.5505 (3) Å	T = 295 K
β = 95.3678 (13)°	Needle, colourless
V = 5383.11 (14) Å3	0.51 × 0.11 × 0.09 mm
Z = 16

Oxford Diffraction Xcalibur diffractometer	Rint = 0.053
graphite	θmax = 25.8°, θmin = 2.3°
ω scans with κ offsets	h = −20→20
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2008), based on Clark & Reid (1995)]	k = −19→19
Tmin = 0.754, Tmax = 0.944	l = −23→23
180094 measured reflections	3 standard reflections every 120 min
10264 independent reflections	intensity decay: 0.5%
5984 reflections with I > 2σ(I)

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0583P)2] where P = (Fo2 + 2Fc2)/3
10278 reflections	(Δ/σ)max < 0.001
670 parameters	Δρmax = 0.33 e Å−3
15 restraints	Δρmin = −0.22 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
N1A	−0.01521 (12)	0.24995 (13)	0.20152 (9)	0.0679 (6)
H1N	−0.0020 (14)	0.2564 (15)	0.1607 (9)	0.081*
O1A	0.00098 (11)	0.27519 (12)	0.31328 (7)	0.0872 (6)
Cl1A	0.34739 (5)	0.42659 (5)	0.23734 (4)	0.1008 (3)
Cl2A	−0.02618 (5)	0.06753 (5)	0.21458 (4)	0.1059 (3)
Cl3A	−0.14461 (5)	0.37320 (5)	0.19803 (4)	0.1009 (3)
C1A	0.02724 (13)	0.27901 (14)	0.25719 (10)	0.0578 (6)
C2A	0.10565 (13)	0.31648 (13)	0.24908 (9)	0.0517 (5)
C3A	0.15350 (15)	0.33685 (15)	0.30778 (11)	0.0658 (6)
H3A	0.1354	0.3275	0.3505	0.079*
C4A	0.22717 (16)	0.37056 (15)	0.30429 (12)	0.0711 (7)
H4A	0.2586	0.3838	0.3443	0.085*
C5A	0.25378 (14)	0.38453 (14)	0.24193 (12)	0.0643 (6)
C6A	0.20812 (16)	0.36548 (17)	0.18329 (12)	0.0800 (8)
H6A	0.2264	0.3757	0.1407	0.096*
C7A	0.13480 (15)	0.33111 (16)	0.18723 (11)	0.0735 (7)
H7A	0.1041	0.3174	0.1469	0.088*
C8A	−0.09215 (14)	0.21751 (17)	0.20417 (10)	0.0627 (6)
C9A	−0.10499 (15)	0.13470 (18)	0.20852 (11)	0.0702 (7)
C10A	−0.18105 (19)	0.10314 (19)	0.20735 (12)	0.0800 (8)
H10A	−0.1888	0.047	0.2109	0.096*
C11A	−0.24487 (17)	0.1553 (2)	0.20087 (12)	0.0820 (8)
H11A	−0.296	0.1342	0.1987	0.098*
C12A	−0.23399 (16)	0.2376 (2)	0.19764 (11)	0.0807 (8)
H12A	−0.2775	0.2726	0.1939	0.097*
C13A	−0.15816 (16)	0.26914 (17)	0.19990 (10)	0.0712 (7)
N1B	0.54004 (11)	0.25961 (12)	0.28954 (8)	0.0578 (5)
H2N	0.5318 (13)	0.2534 (14)	0.2481 (8)	0.069*
O1B	0.49853 (9)	0.25248 (11)	0.39413 (7)	0.0762 (5)
Cl1B	0.17328 (5)	0.09853 (6)	0.22580 (6)	0.1275 (3)
Cl2B	0.65068 (5)	0.13398 (5)	0.35411 (4)	0.1043 (3)
Cl3B	0.56847 (5)	0.43598 (5)	0.26545 (4)	0.1017 (3)
C1B	0.48504 (13)	0.24196 (13)	0.33249 (10)	0.0517 (5)
C2B	0.40793 (12)	0.20796 (12)	0.30239 (10)	0.0484 (5)
C3B	0.35060 (15)	0.19335 (15)	0.34661 (12)	0.0658 (6)
H3B	0.3606	0.2064	0.3929	0.079*
C4B	0.27899 (16)	0.15970 (16)	0.32283 (16)	0.0787 (7)
H4B	0.2407	0.1497	0.353	0.094*
C5B	0.26417 (15)	0.14095 (15)	0.25493 (17)	0.0753 (7)
C6B	0.31894 (17)	0.15589 (18)	0.21067 (14)	0.0841 (8)
H6B	0.308	0.1438	0.1643	0.101*
C7B	0.39097 (15)	0.18910 (15)	0.23434 (11)	0.0700 (7)
H7B	0.4287	0.1989	0.2037	0.084*
C8B	0.61598 (13)	0.28835 (14)	0.31361 (9)	0.0520 (5)
C9B	0.67220 (15)	0.23618 (16)	0.34592 (11)	0.0665 (6)
C10B	0.74665 (17)	0.2637 (2)	0.36897 (13)	0.0840 (8)
H10B	0.7835	0.2283	0.3912	0.101*
C11B	0.76574 (18)	0.3435 (2)	0.35883 (14)	0.0883 (9)
H11B	0.8162	0.3621	0.374	0.106*
C12B	0.71239 (18)	0.39649 (18)	0.32688 (13)	0.0803 (8)
H12B	0.7263	0.4507	0.3199	0.096*
C13B	0.63704 (14)	0.36865 (15)	0.30494 (10)	0.0630 (6)
N1C	0.54579 (11)	0.23320 (10)	0.53835 (8)	0.0508 (4)
H3N	0.5371 (12)	0.2468 (13)	0.4968 (8)	0.061*
O1C	0.56197 (9)	0.27476 (9)	0.64809 (7)	0.0632 (4)
Cl1C	0.62723 (4)	0.63315 (4)	0.49957 (4)	0.0881 (2)
Cl2C	0.38314 (4)	0.16952 (5)	0.55737 (4)	0.0940 (2)
Cl3C	0.69772 (5)	0.14330 (5)	0.54692 (4)	0.1055 (3)
C1C	0.56049 (11)	0.29103 (13)	0.58689 (10)	0.0459 (5)
C2C	0.57685 (11)	0.37500 (12)	0.56292 (9)	0.0441 (5)
C3C	0.56156 (13)	0.44075 (14)	0.60366 (10)	0.0588 (6)
H3C	0.5406	0.4316	0.6453	0.071*
C4C	0.57648 (14)	0.51957 (15)	0.58425 (12)	0.0656 (6)
H4C	0.5645	0.5633	0.6119	0.079*
C5C	0.60899 (12)	0.53327 (13)	0.52411 (11)	0.0554 (6)
C6C	0.62633 (14)	0.46970 (14)	0.48319 (11)	0.0638 (6)
H6C	0.6492	0.4795	0.4426	0.077*
C7C	0.60982 (13)	0.39061 (13)	0.50214 (10)	0.0566 (6)
H7C	0.621	0.3473	0.4737	0.068*
C8C	0.54059 (15)	0.14968 (13)	0.55637 (9)	0.0543 (6)
C9C	0.46937 (16)	0.11342 (14)	0.56777 (11)	0.0653 (6)
C10C	0.4646 (2)	0.03189 (16)	0.58582 (12)	0.0832 (8)
H10C	0.416	0.0085	0.593	0.1*
C11C	0.5325 (3)	−0.01375 (18)	0.59289 (13)	0.0975 (10)
H11C	0.5298	−0.0685	0.6057	0.117*
C12C	0.6042 (2)	0.01942 (19)	0.58145 (13)	0.0915 (9)
H12C	0.6499	−0.0125	0.5859	0.11*
C13C	0.60779 (16)	0.10095 (15)	0.56319 (11)	0.0683 (6)
N1D	1.00625 (13)	0.21879 (12)	0.44495 (8)	0.0716 (6)
H4N	0.9902 (15)	0.2400 (14)	0.4068 (10)	0.086*
O1D	0.98706 (12)	0.21685 (11)	0.55695 (7)	0.0870 (6)
Cl1D	0.82750 (6)	0.58103 (5)	0.47748 (5)	0.1224 (3)
Cl2D	1.17656 (5)	0.21164 (5)	0.49982 (4)	0.1061 (3)
Cl3D	0.90147 (6)	0.08528 (6)	0.38692 (4)	0.1133 (3)
C1D	0.98079 (14)	0.25205 (15)	0.50152 (10)	0.0637 (6)
C2D	0.94263 (13)	0.33420 (15)	0.49198 (10)	0.0574 (6)
C3D	0.88233 (16)	0.35364 (17)	0.53201 (11)	0.0741 (7)
H3D	0.866	0.3153	0.5629	0.089*
C4D	0.84624 (16)	0.42912 (18)	0.52672 (12)	0.0783 (8)
H4D	0.8052	0.4417	0.5534	0.094*
C5D	0.87110 (15)	0.48473 (16)	0.48241 (14)	0.0705 (7)
C6D	0.93043 (15)	0.46719 (15)	0.44139 (12)	0.0681 (6)
H6D	0.9464	0.506	0.4107	0.082*
C7D	0.96600 (13)	0.39125 (15)	0.44644 (11)	0.0589 (6)
H7D	1.0061	0.3786	0.4188	0.071*
C8D	1.04163 (19)	0.14073 (17)	0.44522 (11)	0.0743 (8)
C9D	1.12048 (19)	0.12862 (17)	0.47012 (12)	0.0820 (8)
C10D	1.1547 (2)	0.0528 (2)	0.47083 (15)	0.0975 (10)
H10D	1.2093 (14)	0.046 (2)	0.4889 (15)	0.117*
C11D	1.1102 (3)	−0.0126 (2)	0.44464 (17)	0.1084 (12)
H11D	1.1308 (19)	−0.0659 (15)	0.4433 (16)	0.13*
C12D	1.0336 (3)	−0.0034 (2)	0.41819 (16)	0.1030 (11)
H12D	0.9978 (18)	−0.0453 (18)	0.4045 (16)	0.124*
C13D	0.99924 (19)	0.07337 (19)	0.41871 (12)	0.0846 (8)

	U11	U22	U33	U12	U13	U23
N1A	0.0625 (13)	0.1037 (16)	0.0392 (10)	−0.0228 (11)	0.0139 (9)	−0.0045 (10)
O1A	0.0911 (13)	0.1352 (16)	0.0365 (8)	−0.0286 (11)	0.0115 (8)	0.0063 (9)
Cl1A	0.0782 (5)	0.1158 (6)	0.1075 (5)	−0.0385 (4)	0.0039 (4)	−0.0079 (4)
Cl2A	0.0891 (6)	0.1078 (6)	0.1235 (6)	0.0028 (4)	0.0240 (4)	−0.0029 (5)
Cl3A	0.1086 (6)	0.0957 (6)	0.1020 (5)	−0.0071 (4)	0.0295 (4)	0.0193 (4)
C1A	0.0626 (16)	0.0715 (16)	0.0393 (12)	−0.0033 (12)	0.0053 (11)	0.0076 (10)
C2A	0.0569 (14)	0.0571 (14)	0.0402 (11)	0.0003 (11)	0.0006 (10)	0.0020 (9)
C3A	0.0697 (18)	0.0791 (17)	0.0480 (13)	−0.0042 (14)	0.0024 (11)	0.0017 (11)
C4A	0.0731 (19)	0.0763 (18)	0.0609 (15)	−0.0083 (14)	−0.0096 (13)	−0.0054 (12)
C5A	0.0612 (16)	0.0586 (15)	0.0724 (16)	−0.0085 (12)	0.0024 (13)	−0.0040 (12)
C6A	0.0740 (19)	0.108 (2)	0.0592 (15)	−0.0269 (16)	0.0118 (13)	−0.0024 (13)
C7A	0.0689 (17)	0.104 (2)	0.0466 (13)	−0.0254 (15)	0.0023 (11)	−0.0026 (12)
C8A	0.0577 (17)	0.095 (2)	0.0373 (11)	−0.0174 (15)	0.0132 (10)	0.0008 (11)
C9A	0.0646 (18)	0.092 (2)	0.0552 (14)	−0.0106 (15)	0.0143 (11)	−0.0032 (13)
C10A	0.085 (2)	0.092 (2)	0.0653 (15)	−0.0261 (19)	0.0156 (14)	−0.0031 (13)
C11A	0.0604 (19)	0.122 (3)	0.0647 (16)	−0.0252 (19)	0.0140 (13)	0.0002 (16)
C12A	0.0644 (19)	0.117 (3)	0.0627 (15)	−0.0042 (17)	0.0148 (12)	0.0089 (15)
C13A	0.0693 (19)	0.098 (2)	0.0487 (13)	−0.0138 (16)	0.0171 (11)	0.0058 (12)
N1B	0.0569 (12)	0.0811 (14)	0.0355 (9)	−0.0187 (10)	0.0055 (9)	−0.0068 (9)
O1B	0.0692 (11)	0.1225 (15)	0.0375 (9)	−0.0120 (10)	0.0079 (7)	−0.0091 (8)
Cl1B	0.0605 (5)	0.1105 (7)	0.2077 (10)	−0.0205 (4)	−0.0065 (5)	−0.0284 (6)
Cl2B	0.1170 (7)	0.0748 (5)	0.1224 (6)	0.0019 (4)	0.0172 (5)	0.0197 (4)
Cl3B	0.1091 (6)	0.0838 (5)	0.1127 (5)	0.0075 (4)	0.0135 (5)	0.0211 (4)
C1B	0.0559 (14)	0.0576 (14)	0.0418 (12)	0.0010 (11)	0.0066 (10)	−0.0015 (10)
C2B	0.0500 (13)	0.0466 (12)	0.0490 (12)	0.0026 (10)	0.0069 (10)	0.0033 (9)
C3B	0.0592 (17)	0.0748 (17)	0.0650 (14)	0.0039 (13)	0.0139 (12)	0.0040 (12)
C4B	0.0545 (18)	0.0732 (18)	0.112 (2)	0.0007 (14)	0.0272 (15)	0.0118 (16)
C5B	0.0510 (16)	0.0578 (16)	0.116 (2)	−0.0005 (12)	0.0007 (16)	−0.0101 (15)
C6B	0.0687 (19)	0.101 (2)	0.0806 (17)	−0.0128 (16)	−0.0032 (15)	−0.0196 (15)
C7B	0.0613 (17)	0.0889 (19)	0.0600 (14)	−0.0165 (14)	0.0065 (12)	−0.0091 (12)
C8B	0.0546 (15)	0.0651 (16)	0.0367 (10)	−0.0110 (12)	0.0069 (10)	−0.0084 (10)
C9B	0.0646 (17)	0.0793 (17)	0.0552 (13)	−0.0067 (14)	0.0043 (12)	−0.0062 (12)
C10B	0.067 (2)	0.107 (2)	0.0757 (17)	0.0041 (17)	−0.0062 (14)	−0.0021 (15)
C11B	0.0616 (19)	0.123 (3)	0.0793 (18)	−0.0240 (19)	−0.0015 (14)	−0.0253 (18)
C12B	0.085 (2)	0.0799 (19)	0.0788 (17)	−0.0300 (17)	0.0223 (16)	−0.0221 (15)
C13B	0.0664 (17)	0.0700 (17)	0.0537 (13)	−0.0098 (13)	0.0116 (11)	−0.0087 (11)
N1C	0.0691 (12)	0.0469 (11)	0.0359 (9)	0.0005 (9)	0.0015 (8)	0.0018 (8)
O1C	0.0834 (11)	0.0681 (10)	0.0381 (8)	−0.0007 (8)	0.0063 (7)	0.0022 (7)
Cl1C	0.0757 (5)	0.0547 (4)	0.1344 (6)	−0.0027 (3)	0.0129 (4)	0.0078 (4)
Cl2C	0.0776 (5)	0.0817 (5)	0.1262 (6)	0.0045 (4)	0.0272 (4)	0.0300 (4)
Cl3C	0.0733 (5)	0.1196 (7)	0.1222 (6)	0.0188 (5)	0.0019 (4)	−0.0090 (5)
C1C	0.0435 (13)	0.0566 (14)	0.0376 (12)	0.0071 (10)	0.0036 (9)	−0.0021 (10)
C2C	0.0412 (12)	0.0520 (13)	0.0379 (10)	0.0028 (9)	−0.0020 (9)	−0.0048 (9)
C3C	0.0686 (16)	0.0580 (16)	0.0507 (12)	−0.0006 (12)	0.0103 (11)	−0.0080 (11)
C4C	0.0674 (16)	0.0563 (16)	0.0736 (16)	0.0035 (12)	0.0087 (12)	−0.0192 (12)
C5C	0.0429 (13)	0.0490 (14)	0.0728 (15)	−0.0009 (10)	−0.0029 (11)	0.0017 (11)
C6C	0.0750 (17)	0.0552 (16)	0.0639 (14)	−0.0062 (13)	0.0208 (12)	0.0013 (12)
C7C	0.0664 (16)	0.0504 (14)	0.0546 (13)	0.0009 (11)	0.0143 (11)	−0.0089 (10)
C8C	0.0742 (16)	0.0479 (14)	0.0405 (11)	0.0069 (12)	0.0031 (10)	−0.0007 (9)
C9C	0.0870 (18)	0.0528 (15)	0.0570 (13)	0.0039 (13)	0.0107 (12)	0.0090 (11)
C10C	0.116 (2)	0.0564 (18)	0.0794 (17)	−0.0065 (17)	0.0226 (16)	0.0112 (13)
C11C	0.166 (4)	0.0521 (18)	0.0757 (18)	0.017 (2)	0.018 (2)	0.0114 (13)
C12C	0.129 (3)	0.068 (2)	0.0773 (18)	0.040 (2)	0.0069 (18)	0.0011 (15)
C13C	0.0857 (18)	0.0654 (17)	0.0529 (13)	0.0140 (14)	0.0008 (12)	−0.0059 (11)
N1D	0.1072 (17)	0.0729 (14)	0.0357 (10)	0.0363 (12)	0.0129 (10)	0.0074 (9)
O1D	0.1234 (16)	0.1011 (13)	0.0381 (8)	0.0518 (12)	0.0168 (8)	0.0132 (8)
Cl1D	0.1094 (7)	0.0829 (6)	0.1709 (8)	0.0390 (5)	−0.0071 (6)	−0.0135 (5)
Cl2D	0.1100 (6)	0.1067 (6)	0.1018 (5)	0.0202 (5)	0.0107 (4)	0.0049 (4)
Cl3D	0.1341 (8)	0.1160 (7)	0.0871 (5)	0.0134 (5)	−0.0045 (5)	−0.0027 (4)
C1D	0.0775 (17)	0.0775 (17)	0.0357 (12)	0.0244 (13)	0.0039 (11)	−0.0003 (11)
C2D	0.0624 (15)	0.0749 (16)	0.0336 (10)	0.0183 (12)	−0.0028 (10)	−0.0047 (11)
C3D	0.0843 (19)	0.093 (2)	0.0461 (12)	0.0298 (16)	0.0099 (12)	0.0066 (12)
C4D	0.0760 (19)	0.102 (2)	0.0575 (14)	0.0329 (17)	0.0070 (13)	−0.0023 (15)
C5D	0.0596 (17)	0.0672 (17)	0.0802 (17)	0.0184 (13)	−0.0173 (14)	−0.0169 (14)
C6D	0.0598 (16)	0.0634 (17)	0.0788 (16)	−0.0047 (13)	−0.0056 (13)	−0.0020 (12)
C7D	0.0469 (14)	0.0691 (16)	0.0599 (13)	0.0048 (12)	0.0010 (10)	−0.0093 (12)
C8D	0.116 (2)	0.0710 (19)	0.0386 (12)	0.0345 (18)	0.0239 (13)	0.0051 (12)
C9D	0.109 (2)	0.080 (2)	0.0606 (15)	0.0398 (18)	0.0284 (15)	0.0092 (13)
C10D	0.118 (3)	0.100 (3)	0.0791 (19)	0.048 (2)	0.0332 (18)	0.0100 (17)
C11D	0.160 (4)	0.083 (2)	0.088 (2)	0.058 (2)	0.042 (2)	0.0066 (18)
C12D	0.151 (4)	0.082 (3)	0.080 (2)	0.024 (2)	0.028 (2)	−0.0053 (16)
C13D	0.120 (2)	0.086 (2)	0.0501 (14)	0.0349 (19)	0.0186 (14)	0.0024 (14)

N1A—C1A	1.334 (3)	N1C—C1C	1.345 (2)
N1A—C8A	1.412 (3)	N1C—C8C	1.413 (3)
N1A—H1N	0.855 (16)	N1C—H3N	0.842 (15)
O1A—C1A	1.223 (2)	O1C—C1C	1.224 (2)
Cl1A—C5A	1.738 (2)	Cl1C—C5C	1.736 (2)
Cl2A—C9A	1.723 (3)	Cl2C—C9C	1.720 (3)
Cl3A—C13A	1.715 (3)	Cl3C—C13C	1.729 (3)
C1A—C2A	1.484 (3)	C1C—C2C	1.483 (3)
C2A—C7A	1.369 (3)	C2C—C3C	1.376 (3)
C2A—C3A	1.382 (3)	C2C—C7C	1.383 (3)
C3A—C4A	1.371 (3)	C3C—C4C	1.372 (3)
C3A—H3A	0.93	C3C—H3C	0.93
C4A—C5A	1.358 (3)	C4C—C5C	1.363 (3)
C4A—H4A	0.93	C4C—H4C	0.93
C5A—C6A	1.358 (3)	C5C—C6C	1.359 (3)
C6A—C7A	1.372 (3)	C6C—C7C	1.379 (3)
C6A—H6A	0.93	C6C—H6C	0.93
C7A—H7A	0.93	C7C—H7C	0.93
C8A—C9A	1.373 (3)	C8C—C9C	1.381 (3)
C8A—C13A	1.397 (4)	C8C—C13C	1.385 (3)
C9A—C10A	1.386 (4)	C9C—C10C	1.381 (3)
C10A—C11A	1.373 (4)	C10C—C11C	1.366 (4)
C10A—H10A	0.93	C10C—H10C	0.93
C11A—C12A	1.358 (4)	C11C—C12C	1.368 (4)
C11A—H11A	0.93	C11C—H11C	0.93
C12A—C13A	1.381 (4)	C12C—C13C	1.381 (4)
C12A—H12A	0.93	C12C—H12C	0.93
N1B—C1B	1.343 (3)	N1D—C1D	1.339 (3)
N1B—C8B	1.408 (3)	N1D—C8D	1.408 (3)
N1B—H2N	0.816 (15)	N1D—H4N	0.844 (16)
O1B—C1B	1.218 (2)	O1D—C1D	1.222 (2)
Cl1B—C5B	1.735 (3)	Cl1D—C5D	1.736 (2)
Cl2B—C9B	1.718 (3)	Cl2D—C9D	1.724 (3)
Cl3B—C13B	1.728 (3)	Cl3D—C13D	1.725 (3)
C1B—C2B	1.489 (3)	C1D—C2D	1.493 (3)
C2B—C7B	1.370 (3)	C2D—C7D	1.372 (3)
C2B—C3B	1.380 (3)	C2D—C3D	1.381 (3)
C3B—C4B	1.373 (4)	C3D—C4D	1.375 (3)
C3B—H3B	0.93	C3D—H3D	0.93
C4B—C5B	1.363 (4)	C4D—C5D	1.349 (4)
C4B—H4B	0.93	C4D—H4D	0.93
C5B—C6B	1.349 (4)	C5D—C6D	1.373 (3)
C6B—C7B	1.375 (3)	C6D—C7D	1.378 (3)
C6B—H6B	0.93	C6D—H6D	0.93
C7B—H7B	0.93	C7D—H7D	0.93
C8B—C13B	1.373 (3)	C8D—C13D	1.387 (4)
C8B—C9B	1.385 (3)	C8D—C9D	1.392 (4)
C9B—C10B	1.375 (3)	C9D—C10D	1.366 (4)
C10B—C11B	1.360 (4)	C10D—C11D	1.378 (5)
C10B—H10B	0.93	C10D—H10D	0.96 (2)
C11B—C12B	1.361 (4)	C11D—C12D	1.360 (5)
C11B—H11B	0.93	C11D—H11D	0.94 (2)
C12B—C13B	1.385 (3)	C12D—C13D	1.382 (4)
C12B—H12B	0.93	C12D—H12D	0.94 (2)
C1A—N1A—C8A	122.16 (17)	C1C—N1C—C8C	120.87 (16)
C1A—N1A—H1N	123.3 (17)	C1C—N1C—H3N	119.9 (15)
C8A—N1A—H1N	113.8 (17)	C8C—N1C—H3N	119.1 (15)
O1A—C1A—N1A	120.0 (2)	O1C—C1C—N1C	121.53 (19)
O1A—C1A—C2A	121.40 (19)	O1C—C1C—C2C	121.48 (17)
N1A—C1A—C2A	118.61 (18)	N1C—C1C—C2C	116.97 (16)
C7A—C2A—C3A	117.3 (2)	C3C—C2C—C7C	117.8 (2)
C7A—C2A—C1A	124.51 (19)	C3C—C2C—C1C	119.17 (18)
C3A—C2A—C1A	118.14 (19)	C7C—C2C—C1C	122.96 (18)
C4A—C3A—C2A	121.4 (2)	C4C—C3C—C2C	121.5 (2)
C4A—C3A—H3A	119.3	C4C—C3C—H3C	119.3
C2A—C3A—H3A	119.3	C2C—C3C—H3C	119.3
C5A—C4A—C3A	119.5 (2)	C5C—C4C—C3C	119.5 (2)
C5A—C4A—H4A	120.3	C5C—C4C—H4C	120.3
C3A—C4A—H4A	120.3	C3C—C4C—H4C	120.3
C6A—C5A—C4A	120.6 (2)	C6C—C5C—C4C	120.6 (2)
C6A—C5A—Cl1A	119.8 (2)	C6C—C5C—Cl1C	120.05 (18)
C4A—C5A—Cl1A	119.59 (19)	C4C—C5C—Cl1C	119.30 (18)
C5A—C6A—C7A	119.6 (2)	C5C—C6C—C7C	119.7 (2)
C5A—C6A—H6A	120.2	C5C—C6C—H6C	120.1
C7A—C6A—H6A	120.2	C7C—C6C—H6C	120.1
C2A—C7A—C6A	121.6 (2)	C6C—C7C—C2C	120.78 (19)
C2A—C7A—H7A	119.2	C6C—C7C—H7C	119.6
C6A—C7A—H7A	119.2	C2C—C7C—H7C	119.6
C9A—C8A—C13A	117.9 (2)	C9C—C8C—C13C	117.5 (2)
C9A—C8A—N1A	121.6 (2)	C9C—C8C—N1C	122.0 (2)
C13A—C8A—N1A	120.5 (2)	C13C—C8C—N1C	120.6 (2)
C8A—C9A—C10A	121.1 (3)	C8C—C9C—C10C	121.8 (2)
C8A—C9A—Cl2A	120.3 (2)	C8C—C9C—Cl2C	119.87 (17)
C10A—C9A—Cl2A	118.5 (2)	C10C—C9C—Cl2C	118.3 (2)
C11A—C10A—C9A	119.6 (3)	C11C—C10C—C9C	118.8 (3)
C11A—C10A—H10A	120.2	C11C—C10C—H10C	120.6
C9A—C10A—H10A	120.2	C9C—C10C—H10C	120.6
C12A—C11A—C10A	120.6 (3)	C10C—C11C—C12C	121.3 (3)
C12A—C11A—H11A	119.7	C10C—C11C—H11C	119.3
C10A—C11A—H11A	119.7	C12C—C11C—H11C	119.3
C11A—C12A—C13A	119.8 (3)	C11C—C12C—C13C	119.0 (3)
C11A—C12A—H12A	120.1	C11C—C12C—H12C	120.5
C13A—C12A—H12A	120.1	C13C—C12C—H12C	120.5
C12A—C13A—C8A	121.0 (3)	C12C—C13C—C8C	121.5 (3)
C12A—C13A—Cl3A	119.6 (2)	C12C—C13C—Cl3C	119.6 (2)
C8A—C13A—Cl3A	119.4 (2)	C8C—C13C—Cl3C	118.9 (2)
C1B—N1B—C8B	121.88 (16)	C1D—N1D—C8D	122.27 (18)
C1B—N1B—H2N	122.1 (16)	C1D—N1D—H4N	117.4 (17)
C8B—N1B—H2N	116.1 (16)	C8D—N1D—H4N	118.5 (17)
O1B—C1B—N1B	120.78 (19)	O1D—C1D—N1D	122.2 (2)
O1B—C1B—C2B	121.35 (19)	O1D—C1D—C2D	122.27 (19)
N1B—C1B—C2B	117.86 (17)	N1D—C1D—C2D	115.48 (18)
C7B—C2B—C3B	118.3 (2)	C7D—C2D—C3D	119.0 (2)
C7B—C2B—C1B	124.35 (19)	C7D—C2D—C1D	122.9 (2)
C3B—C2B—C1B	117.37 (18)	C3D—C2D—C1D	118.1 (2)
C4B—C3B—C2B	120.6 (2)	C4D—C3D—C2D	120.7 (2)
C4B—C3B—H3B	119.7	C4D—C3D—H3D	119.6
C2B—C3B—H3B	119.7	C2D—C3D—H3D	119.6
C5B—C4B—C3B	119.8 (2)	C5D—C4D—C3D	119.2 (2)
C5B—C4B—H4B	120.1	C5D—C4D—H4D	120.4
C3B—C4B—H4B	120.1	C3D—C4D—H4D	120.4
C6B—C5B—C4B	120.6 (2)	C4D—C5D—C6D	121.6 (2)
C6B—C5B—Cl1B	120.3 (2)	C4D—C5D—Cl1D	119.2 (2)
C4B—C5B—Cl1B	119.1 (2)	C6D—C5D—Cl1D	119.2 (2)
C5B—C6B—C7B	119.8 (2)	C5D—C6D—C7D	119.0 (2)
C5B—C6B—H6B	120.1	C5D—C6D—H6D	120.5
C7B—C6B—H6B	120.1	C7D—C6D—H6D	120.5
C2B—C7B—C6B	121.0 (2)	C2D—C7D—C6D	120.4 (2)
C2B—C7B—H7B	119.5	C2D—C7D—H7D	119.8
C6B—C7B—H7B	119.5	C6D—C7D—H7D	119.8
C13B—C8B—C9B	117.9 (2)	C13D—C8D—C9D	117.7 (2)
C13B—C8B—N1B	121.1 (2)	C13D—C8D—N1D	120.7 (3)
C9B—C8B—N1B	121.0 (2)	C9D—C8D—N1D	121.6 (3)
C10B—C9B—C8B	121.3 (2)	C10D—C9D—C8D	121.6 (3)
C10B—C9B—Cl2B	118.9 (2)	C10D—C9D—Cl2D	119.2 (3)
C8B—C9B—Cl2B	119.77 (19)	C8D—C9D—Cl2D	119.1 (2)
C11B—C10B—C9B	119.3 (3)	C9D—C10D—C11D	118.8 (3)
C11B—C10B—H10B	120.4	C9D—C10D—H10D	120 (2)
C9B—C10B—H10B	120.4	C11D—C10D—H10D	121 (2)
C10B—C11B—C12B	121.3 (3)	C12D—C11D—C10D	121.6 (3)
C10B—C11B—H11B	119.4	C12D—C11D—H11D	116 (2)
C12B—C11B—H11B	119.4	C10D—C11D—H11D	123 (2)
C11B—C12B—C13B	119.1 (3)	C11D—C12D—C13D	119.1 (3)
C11B—C12B—H12B	120.4	C11D—C12D—H12D	127 (2)
C13B—C12B—H12B	120.4	C13D—C12D—H12D	114 (2)
C8B—C13B—C12B	121.2 (2)	C12D—C13D—C8D	121.2 (3)
C8B—C13B—Cl3B	119.39 (19)	C12D—C13D—Cl3D	119.4 (3)
C12B—C13B—Cl3B	119.4 (2)	C8D—C13D—Cl3D	119.4 (2)
C8A—N1A—C1A—O1A	2.8 (4)	C8C—N1C—C1C—O1C	−7.4 (3)
C8A—N1A—C1A—C2A	−176.4 (2)	C8C—N1C—C1C—C2C	171.07 (18)
O1A—C1A—C2A—C7A	−172.4 (2)	O1C—C1C—C2C—C3C	−27.0 (3)
N1A—C1A—C2A—C7A	6.9 (4)	N1C—C1C—C2C—C3C	154.53 (19)
O1A—C1A—C2A—C3A	8.9 (3)	O1C—C1C—C2C—C7C	150.5 (2)
N1A—C1A—C2A—C3A	−171.9 (2)	N1C—C1C—C2C—C7C	−28.0 (3)
C7A—C2A—C3A—C4A	0.2 (4)	C7C—C2C—C3C—C4C	1.6 (3)
C1A—C2A—C3A—C4A	179.0 (2)	C1C—C2C—C3C—C4C	179.2 (2)
C2A—C3A—C4A—C5A	0.2 (4)	C2C—C3C—C4C—C5C	−1.6 (3)
C3A—C4A—C5A—C6A	0.0 (4)	C3C—C4C—C5C—C6C	0.3 (3)
C3A—C4A—C5A—Cl1A	−179.6 (2)	C3C—C4C—C5C—Cl1C	179.65 (17)
C4A—C5A—C6A—C7A	−0.6 (4)	C4C—C5C—C6C—C7C	1.0 (3)
Cl1A—C5A—C6A—C7A	179.0 (2)	Cl1C—C5C—C6C—C7C	−178.36 (17)
C3A—C2A—C7A—C6A	−0.8 (4)	C5C—C6C—C7C—C2C	−1.0 (3)
C1A—C2A—C7A—C6A	−179.5 (2)	C3C—C2C—C7C—C6C	−0.3 (3)
C5A—C6A—C7A—C2A	1.0 (4)	C1C—C2C—C7C—C6C	−177.8 (2)
C1A—N1A—C8A—C9A	−97.7 (3)	C1C—N1C—C8C—C9C	91.7 (2)
C1A—N1A—C8A—C13A	84.6 (3)	C1C—N1C—C8C—C13C	−88.3 (2)
C13A—C8A—C9A—C10A	1.3 (3)	C13C—C8C—C9C—C10C	0.5 (3)
N1A—C8A—C9A—C10A	−176.47 (19)	N1C—C8C—C9C—C10C	−179.56 (19)
C13A—C8A—C9A—Cl2A	−179.50 (15)	C13C—C8C—C9C—Cl2C	−177.83 (15)
N1A—C8A—C9A—Cl2A	2.8 (3)	N1C—C8C—C9C—Cl2C	2.1 (3)
C8A—C9A—C10A—C11A	0.8 (3)	C8C—C9C—C10C—C11C	0.4 (4)
Cl2A—C9A—C10A—C11A	−178.44 (18)	Cl2C—C9C—C10C—C11C	178.7 (2)
C9A—C10A—C11A—C12A	−1.9 (4)	C9C—C10C—C11C—C12C	−1.0 (4)
C10A—C11A—C12A—C13A	0.9 (4)	C10C—C11C—C12C—C13C	0.8 (4)
C11A—C12A—C13A—C8A	1.2 (3)	C11C—C12C—C13C—C8C	0.1 (4)
C11A—C12A—C13A—Cl3A	−178.34 (18)	C11C—C12C—C13C—Cl3C	−178.7 (2)
C9A—C8A—C13A—C12A	−2.3 (3)	C9C—C8C—C13C—C12C	−0.7 (3)
N1A—C8A—C13A—C12A	175.46 (19)	N1C—C8C—C13C—C12C	179.31 (19)
C9A—C8A—C13A—Cl3A	177.28 (16)	C9C—C8C—C13C—Cl3C	178.16 (16)
N1A—C8A—C13A—Cl3A	−5.0 (3)	N1C—C8C—C13C—Cl3C	−1.8 (3)
C8B—N1B—C1B—O1B	2.0 (3)	C8D—N1D—C1D—O1D	0.4 (4)
C8B—N1B—C1B—C2B	−176.97 (19)	C8D—N1D—C1D—C2D	−178.3 (3)
O1B—C1B—C2B—C7B	−175.1 (2)	O1D—C1D—C2D—C7D	147.4 (2)
N1B—C1B—C2B—C7B	3.9 (3)	N1D—C1D—C2D—C7D	−33.9 (3)
O1B—C1B—C2B—C3B	3.7 (3)	O1D—C1D—C2D—C3D	−31.2 (3)
N1B—C1B—C2B—C3B	−177.3 (2)	N1D—C1D—C2D—C3D	147.5 (2)
C7B—C2B—C3B—C4B	0.9 (3)	C7D—C2D—C3D—C4D	−0.3 (3)
C1B—C2B—C3B—C4B	−178.0 (2)	C1D—C2D—C3D—C4D	178.4 (2)
C2B—C3B—C4B—C5B	−0.3 (4)	C2D—C3D—C4D—C5D	−0.8 (4)
C3B—C4B—C5B—C6B	−0.7 (4)	C3D—C4D—C5D—C6D	1.4 (4)
C3B—C4B—C5B—Cl1B	−180.0 (2)	C3D—C4D—C5D—Cl1D	−178.18 (19)
C4B—C5B—C6B—C7B	1.1 (4)	C4D—C5D—C6D—C7D	−0.9 (4)
Cl1B—C5B—C6B—C7B	−179.6 (2)	Cl1D—C5D—C6D—C7D	178.70 (16)
C3B—C2B—C7B—C6B	−0.5 (4)	C3D—C2D—C7D—C6D	0.8 (3)
C1B—C2B—C7B—C6B	178.3 (2)	C1D—C2D—C7D—C6D	−177.8 (2)
C5B—C6B—C7B—C2B	−0.5 (4)	C5D—C6D—C7D—C2D	−0.3 (3)
C1B—N1B—C8B—C13B	−107.0 (2)	C1D—N1D—C8D—C13D	102.9 (3)
C1B—N1B—C8B—C9B	73.9 (3)	C1D—N1D—C8D—C9D	−78.9 (3)
C13B—C8B—C9B—C10B	0.3 (3)	C13D—C8D—C9D—C10D	−2.2 (4)
N1B—C8B—C9B—C10B	179.4 (2)	N1D—C8D—C9D—C10D	179.6 (2)
C13B—C8B—C9B—Cl2B	−176.64 (16)	C13D—C8D—C9D—Cl2D	177.01 (17)
N1B—C8B—C9B—Cl2B	2.4 (3)	N1D—C8D—C9D—Cl2D	−1.2 (3)
C8B—C9B—C10B—C11B	−1.0 (4)	C8D—C9D—C10D—C11D	1.6 (4)
Cl2B—C9B—C10B—C11B	175.9 (2)	Cl2D—C9D—C10D—C11D	−177.6 (2)
C9B—C10B—C11B—C12B	0.6 (4)	C9D—C10D—C11D—C12D	0.1 (5)
C10B—C11B—C12B—C13B	0.6 (4)	C10D—C11D—C12D—C13D	−1.1 (5)
C9B—C8B—C13B—C12B	0.9 (3)	C11D—C12D—C13D—C8D	0.4 (4)
N1B—C8B—C13B—C12B	−178.19 (19)	C11D—C12D—C13D—Cl3D	−178.7 (2)
C9B—C8B—C13B—Cl3B	−179.54 (15)	C9D—C8D—C13D—C12D	1.2 (4)
N1B—C8B—C13B—Cl3B	1.4 (3)	N1D—C8D—C13D—C12D	179.4 (2)
C11B—C12B—C13B—C8B	−1.4 (3)	C9D—C8D—C13D—Cl3D	−179.74 (17)
C11B—C12B—C13B—Cl3B	179.1 (2)	N1D—C8D—C13D—Cl3D	−1.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1N···O1Di	0.86 (2)	2.07 (2)	2.882 (2)	159 (2)
N1B—H2N···O1Cii	0.82 (2)	2.12 (2)	2.880 (2)	156 (2)
N1C—H3N···O1B	0.84 (2)	2.05 (2)	2.875 (2)	165 (2)
N1D—H4N···O1Aiii	0.84 (2)	1.94 (2)	2.728 (2)	154 (2)
C7A—H7A···O1Di	0.93	2.59	3.489 (3)	164
C10C—H10C···Cl2Biv	0.93	2.82	3.599 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1N⋯O1Di	0.855 (16)	2.066 (17)	2.882 (2)	159 (2)
N1B—H2N⋯O1Cii	0.816 (15)	2.117 (17)	2.880 (2)	156 (2)
N1C—H3N⋯O1B	0.842 (15)	2.054 (16)	2.875 (2)	165 (2)
N1D—H4N⋯O1Aiii	0.844 (16)	1.942 (19)	2.728 (2)	154 (2)
C7A—H7A⋯O1Di	0.93	2.59	3.489 (3)	164
C10C—H10C⋯Cl2Biv	0.93	2.82	3.599 (3)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .