1,8-Bis(3-chloro-anilino)-N,N'-bis-(3-chloro-phen-yl)octane-1,8-diimine.

There are two half-mol-ecules in the asymmetric unit of the title compound, C(32)H(30)Cl(4)N(4), in both of which the N-H bonds are syn to the meta-chloro substituents in the adjacent benzene ring. The other two Cl atoms of these two mol-ecules are disordered with occunpancy ratios of 0.79 (2):0.21 (2) and 0.68 (1):0.32 (1). Adjacent chloro-phenyl rings make dihedral angles of 74.3 (2) and 63.0 (2)° in the two mol-ecules. In the crystal, inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into infinite chains.

Related literature

For our study on the effect of substituents on the structures of this class of compounds, see: Gowda et al. (2007 ▶, 2009 ▶, 2010 ▶).

Experimental

Crystal data

C32H30Cl4N4

M = 612.40

Monoclinic,

a = 22.349 (3) Å

b = 13.223 (2) Å

c = 22.644 (3) Å

β = 108.79 (1)°

V = 6335.1 (15) Å3

Z = 8

Cu Kα radiation

μ = 3.61 mm−1

T = 299 K

0.35 × 0.28 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.365, T max = 0.466

11300 measured reflections

5657 independent reflections

3976 reflections with I > 2σ(I)

R int = 0.057

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.251

S = 1.13

5657 reflections

381 parameters

41 restraints

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.80 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004612/bq2276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004612/bq2276Isup2.hkl

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

C32H30Cl4N4	F(000) = 2544
Mr = 612.40	Dx = 1.284 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 22.349 (3) Å	θ = 4.1–18.3°
b = 13.223 (2) Å	µ = 3.61 mm−1
c = 22.644 (3) Å	T = 299 K
β = 108.79 (1)°	Prism, colourless
V = 6335.1 (15) Å3	0.35 × 0.28 × 0.25 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	3976 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
graphite	θmax = 67.0°, θmin = 3.9°
ω/2θ scans	h = −26→26
Absorption correction: ψ scan (North et al., 1968)	k = −15→0
Tmin = 0.365, Tmax = 0.466	l = −27→27
11300 measured reflections	3 standard reflections every 120 min
5657 independent reflections	intensity decay: 1.0%

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.251	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.1192P)2 + 8.1108P] where P = (Fo2 + 2Fc2)/3
5657 reflections	(Δ/σ)max = 0.012
381 parameters	Δρmax = 1.08 e Å−3
41 restraints	Δρmin = −0.80 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)
C1	0.63535 (16)	0.8110 (3)	0.10493 (18)	0.0540 (9)
C2	0.61041 (18)	0.7419 (4)	0.0579 (2)	0.0638 (11)
H2	0.6206	0.6737	0.0650	0.077*
C3	0.57069 (19)	0.7723 (5)	0.0006 (2)	0.0774 (14)
C4	0.5548 (2)	0.8728 (5)	−0.0114 (3)	0.0926 (18)
H4	0.5283	0.8933	−0.0504	0.111*
C5	0.5787 (2)	0.9407 (5)	0.0347 (3)	0.0955 (19)
H5	0.5678	1.0085	0.0272	0.115*
C6	0.6187 (2)	0.9125 (4)	0.0929 (3)	0.0751 (13)
H6	0.6344	0.9609	0.1238	0.090*
C7	0.66481 (15)	0.7380 (3)	0.20450 (18)	0.0492 (8)
C8	0.77434 (16)	0.6888 (3)	0.26857 (18)	0.0478 (8)
C9	0.80067 (18)	0.6761 (3)	0.2217 (2)	0.0620 (10)
H9	0.7756	0.6764	0.1799	0.074*
C10	0.8655 (2)	0.6627 (4)	0.2385 (3)	0.0802 (14)
C11	0.9041 (2)	0.6637 (5)	0.2994 (3)	0.0901 (17)
H11	0.9477	0.6566	0.3095	0.108*
C12	0.8765 (2)	0.6757 (4)	0.3453 (3)	0.0830 (15)
H12	0.9015	0.6754	0.3870	0.100*
C13	0.8120 (2)	0.6880 (3)	0.3298 (2)	0.0657 (11)
H13	0.7939	0.6958	0.3611	0.079*
C14	0.59767 (18)	0.7315 (4)	0.2054 (2)	0.0710 (13)
H14A	0.5928	0.6712	0.2278	0.085*
H14B	0.5690	0.7264	0.1631	0.085*
C15	0.5809 (3)	0.8240 (6)	0.2367 (3)	0.117 (2)
H15A	0.5921	0.8852	0.2190	0.140*
H15B	0.6038	0.8231	0.2810	0.140*
C16	0.5112 (4)	0.8207 (10)	0.2255 (3)	0.199 (4)
H16A	0.4926	0.8784	0.1996	0.238*
H16B	0.4949	0.7606	0.2011	0.238*
C17	0.63312 (17)	0.6138 (3)	0.38310 (17)	0.0518 (9)
C18	0.6569 (2)	0.7033 (4)	0.4113 (2)	0.0776 (14)
H18	0.6913	0.7335	0.4038	0.093*
C19	0.6292 (3)	0.7482 (4)	0.4511 (3)	0.0897 (16)
C20	0.5771 (2)	0.7112 (5)	0.4608 (2)	0.0844 (15)
H20	0.5567	0.7467	0.4842	0.101*
C21	0.5554 (3)	0.6213 (5)	0.4355 (3)	0.0998 (19)
H21	0.5220	0.5910	0.4449	0.120*
C22	0.5819 (3)	0.5725 (4)	0.3954 (3)	0.0885 (17)
H22	0.5649	0.5117	0.3769	0.106*
C23	0.69546 (16)	0.4917 (3)	0.35604 (16)	0.0447 (8)
C24	0.68501 (19)	0.4508 (3)	0.24635 (17)	0.0528 (9)
C25	0.7241 (2)	0.4475 (3)	0.21015 (19)	0.0644 (11)
H25	0.7677	0.4434	0.2285	0.077*
C26	0.6968 (4)	0.4506 (4)	0.1452 (2)	0.0906 (18)
C27	0.6336 (4)	0.4577 (5)	0.1182 (3)	0.104 (2)
H27	0.6162	0.4606	0.0750	0.125*
C28	0.5958 (3)	0.4607 (5)	0.1543 (3)	0.110 (2)
H28	0.5522	0.4660	0.1356	0.132*
C29	0.6208 (2)	0.4560 (4)	0.2186 (2)	0.0784 (13)
H29	0.5942	0.4564	0.2429	0.094*
C30	0.72564 (18)	0.4535 (3)	0.42161 (16)	0.0509 (8)
H30A	0.7085	0.4913	0.4492	0.061*
H30B	0.7706	0.4673	0.4342	0.061*
C31	0.71619 (18)	0.3416 (3)	0.43018 (17)	0.0526 (9)
H31A	0.7307	0.3034	0.4008	0.063*
H31B	0.6715	0.3281	0.4211	0.063*
C32	0.75182 (19)	0.3065 (3)	0.49619 (17)	0.0524 (9)
H32A	0.7958	0.3263	0.5067	0.063*
H32B	0.7344	0.3400	0.5251	0.063*
Cl1	0.53949 (8)	0.68487 (18)	−0.05730 (8)	0.1244 (7)
Cl2A	0.8972 (3)	0.6372 (10)	0.1775 (3)	0.125 (2)	0.79 (2)
Cl2B	0.9069 (5)	0.695 (2)	0.1895 (8)	0.092 (6)	0.21 (2)
Cl3	0.74629 (14)	0.44327 (16)	0.10060 (9)	0.1560 (10)
Cl4A	0.6688 (3)	0.8514 (4)	0.4962 (3)	0.123 (2)	0.677 (14)
Cl4B	0.6346 (7)	0.8849 (7)	0.4577 (9)	0.154 (4)	0.323 (14)
N1	0.68110 (12)	0.7822 (2)	0.16139 (14)	0.0510 (7)
N2	0.70837 (13)	0.6998 (2)	0.25587 (14)	0.0508 (7)
H2A	0.6941	0.6794	0.2848	0.061*
N3	0.65826 (15)	0.5678 (2)	0.33991 (14)	0.0522 (7)
N4	0.71358 (15)	0.4416 (2)	0.31194 (13)	0.0519 (7)
H4A	0.7451	0.4009	0.3250	0.062*

	U11	U22	U33	U12	U13	U23
C1	0.0362 (16)	0.065 (2)	0.063 (2)	−0.0013 (16)	0.0191 (16)	0.0114 (19)
C2	0.049 (2)	0.075 (3)	0.072 (3)	−0.0037 (19)	0.026 (2)	0.006 (2)
C3	0.044 (2)	0.118 (4)	0.071 (3)	−0.013 (2)	0.020 (2)	0.001 (3)
C4	0.058 (3)	0.120 (5)	0.089 (4)	0.004 (3)	0.008 (3)	0.038 (4)
C5	0.062 (3)	0.090 (4)	0.120 (5)	0.011 (3)	0.009 (3)	0.040 (4)
C6	0.054 (2)	0.064 (3)	0.098 (3)	0.0056 (19)	0.013 (2)	0.016 (3)
C7	0.0392 (17)	0.050 (2)	0.064 (2)	0.0006 (14)	0.0234 (16)	0.0047 (17)
C8	0.0425 (17)	0.0381 (17)	0.063 (2)	0.0004 (14)	0.0169 (16)	0.0077 (16)
C9	0.050 (2)	0.072 (3)	0.069 (3)	0.0139 (18)	0.0263 (19)	0.016 (2)
C10	0.053 (2)	0.097 (4)	0.100 (4)	0.020 (2)	0.037 (2)	0.030 (3)
C11	0.047 (2)	0.103 (4)	0.115 (4)	0.011 (2)	0.018 (3)	0.027 (3)
C12	0.057 (2)	0.091 (4)	0.085 (3)	0.001 (2)	0.000 (2)	0.009 (3)
C13	0.061 (2)	0.067 (3)	0.065 (3)	0.003 (2)	0.016 (2)	0.003 (2)
C14	0.0414 (19)	0.096 (3)	0.082 (3)	−0.001 (2)	0.0286 (19)	0.024 (3)
C15	0.077 (3)	0.177 (7)	0.113 (5)	0.050 (4)	0.055 (3)	0.009 (5)
C16	0.107 (5)	0.317 (10)	0.190 (8)	0.058 (6)	0.072 (5)	−0.038 (7)
C17	0.054 (2)	0.055 (2)	0.0505 (19)	0.0127 (16)	0.0225 (16)	0.0046 (17)
C18	0.080 (3)	0.076 (3)	0.094 (3)	−0.015 (2)	0.053 (3)	−0.026 (3)
C19	0.109 (4)	0.082 (3)	0.101 (4)	−0.013 (3)	0.065 (3)	−0.032 (3)
C20	0.077 (3)	0.104 (4)	0.085 (3)	0.007 (3)	0.044 (3)	−0.025 (3)
C21	0.083 (3)	0.127 (5)	0.113 (4)	−0.023 (3)	0.064 (3)	−0.032 (4)
C22	0.093 (3)	0.089 (4)	0.107 (4)	−0.028 (3)	0.064 (3)	−0.032 (3)
C23	0.0500 (18)	0.0448 (18)	0.0433 (17)	0.0003 (15)	0.0206 (15)	0.0021 (15)
C24	0.072 (2)	0.0434 (19)	0.0433 (18)	0.0061 (17)	0.0195 (17)	−0.0022 (16)
C25	0.100 (3)	0.047 (2)	0.054 (2)	0.008 (2)	0.036 (2)	0.0037 (18)
C26	0.172 (6)	0.054 (3)	0.060 (3)	0.016 (3)	0.056 (3)	0.003 (2)
C27	0.152 (5)	0.081 (4)	0.058 (3)	0.024 (4)	0.003 (3)	−0.004 (3)
C28	0.112 (5)	0.107 (5)	0.079 (4)	0.022 (4)	−0.014 (4)	−0.022 (4)
C29	0.075 (3)	0.083 (3)	0.067 (3)	0.004 (2)	0.008 (2)	−0.010 (2)
C30	0.059 (2)	0.051 (2)	0.0449 (19)	0.0078 (16)	0.0199 (16)	0.0033 (16)
C31	0.056 (2)	0.054 (2)	0.049 (2)	0.0063 (16)	0.0190 (16)	0.0091 (16)
C32	0.062 (2)	0.054 (2)	0.0449 (18)	0.0097 (17)	0.0221 (16)	0.0059 (16)
Cl1	0.0920 (10)	0.187 (2)	0.0875 (10)	−0.0210 (11)	0.0193 (8)	−0.0408 (11)
Cl2A	0.0884 (18)	0.174 (6)	0.139 (2)	0.049 (3)	0.0729 (17)	0.027 (3)
Cl2B	0.056 (4)	0.138 (11)	0.096 (6)	0.032 (5)	0.043 (4)	0.032 (6)
Cl3	0.283 (3)	0.1340 (16)	0.1014 (12)	0.0364 (16)	0.1314 (17)	0.0228 (11)
Cl4A	0.159 (4)	0.116 (3)	0.124 (3)	−0.053 (2)	0.088 (3)	−0.066 (2)
Cl4B	0.195 (8)	0.116 (5)	0.171 (9)	0.002 (5)	0.088 (7)	−0.069 (5)
N1	0.0355 (14)	0.0593 (18)	0.0599 (18)	−0.0003 (12)	0.0177 (13)	0.0126 (15)
N2	0.0437 (15)	0.0574 (18)	0.0564 (17)	0.0006 (13)	0.0232 (13)	0.0100 (14)
N3	0.0661 (19)	0.0493 (17)	0.0488 (16)	0.0118 (14)	0.0293 (14)	0.0063 (14)
N4	0.0592 (17)	0.0569 (18)	0.0432 (15)	0.0162 (14)	0.0216 (13)	0.0029 (13)

C1—C2	1.378 (6)	C17—C22	1.375 (6)
C1—C6	1.395 (6)	C17—N3	1.413 (5)
C1—N1	1.409 (5)	C18—C19	1.383 (6)
C2—C3	1.375 (6)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.344 (7)
C3—C4	1.380 (8)	C19—Cl4A	1.763 (6)
C3—Cl1	1.718 (6)	C19—Cl4B	1.815 (10)
C4—C5	1.351 (9)	C20—C21	1.340 (8)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.384 (7)	C21—C22	1.391 (7)
C5—H5	0.9300	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—N1	1.287 (5)	C23—N3	1.281 (5)
C7—N2	1.351 (5)	C23—N4	1.364 (4)
C7—C14	1.510 (5)	C23—C30	1.506 (5)
C8—C13	1.370 (6)	C24—C29	1.371 (6)
C8—C9	1.381 (6)	C24—C25	1.377 (6)
C8—N2	1.416 (4)	C24—N4	1.420 (5)
C9—C10	1.386 (6)	C25—C26	1.399 (7)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.371 (8)	C26—C27	1.348 (9)
C10—Cl2B	1.712 (10)	C26—Cl3	1.725 (6)
C10—Cl2A	1.777 (7)	C27—C28	1.353 (10)
C11—C12	1.378 (8)	C27—H27	0.9300
C11—H11	0.9300	C28—C29	1.383 (8)
C12—C13	1.379 (6)	C28—H28	0.9300
C12—H12	0.9300	C29—H29	0.9300
C13—H13	0.9300	C30—C31	1.516 (5)
C14—C15	1.518 (8)	C30—H30A	0.9700
C14—H14A	0.9700	C30—H30B	0.9700
C14—H14B	0.9700	C31—C32	1.522 (5)
C15—C16	1.498 (10)	C31—H31A	0.9700
C15—H15A	0.9700	C31—H31B	0.9700
C15—H15B	0.9700	C32—C32ii	1.509 (8)
C16—C16i	1.355 (9)	C32—H32A	0.9700
C16—H16A	0.9700	C32—H32B	0.9700
C16—H16B	0.9700	N2—H2A	0.8600
C17—C18	1.368 (6)	N4—H4A	0.8600
C2—C1—C6	118.1 (4)	C17—C18—H18	120.4
C2—C1—N1	121.1 (4)	C19—C18—H18	120.4
C6—C1—N1	120.5 (4)	C20—C19—C18	122.9 (5)
C3—C2—C1	120.8 (5)	C20—C19—Cl4A	119.2 (4)
C3—C2—H2	119.6	C18—C19—Cl4A	117.6 (4)
C1—C2—H2	119.6	C20—C19—Cl4B	112.8 (5)
C2—C3—C4	121.0 (5)	C18—C19—Cl4B	116.7 (5)
C2—C3—Cl1	120.2 (5)	C21—C20—C19	117.8 (5)
C4—C3—Cl1	118.8 (4)	C21—C20—H20	121.1
C5—C4—C3	118.3 (5)	C19—C20—H20	121.1
C5—C4—H4	120.8	C20—C21—C22	121.3 (5)
C3—C4—H4	120.8	C20—C21—H21	119.4
C4—C5—C6	122.0 (5)	C22—C21—H21	119.4
C4—C5—H5	119.0	C17—C22—C21	120.3 (5)
C6—C5—H5	119.0	C17—C22—H22	119.8
C5—C6—C1	119.7 (5)	C21—C22—H22	119.8
C5—C6—H6	120.1	N3—C23—N4	119.4 (3)
C1—C6—H6	120.1	N3—C23—C30	126.0 (3)
N1—C7—N2	121.4 (3)	N4—C23—C30	114.5 (3)
N1—C7—C14	124.2 (3)	C29—C24—C25	120.0 (4)
N2—C7—C14	114.2 (3)	C29—C24—N4	122.3 (4)
C13—C8—C9	120.1 (3)	C25—C24—N4	117.5 (4)
C13—C8—N2	117.8 (3)	C24—C25—C26	118.6 (5)
C9—C8—N2	122.0 (3)	C24—C25—H25	120.7
C8—C9—C10	118.1 (4)	C26—C25—H25	120.7
C8—C9—H9	121.0	C27—C26—C25	121.1 (5)
C10—C9—H9	121.0	C27—C26—Cl3	120.9 (5)
C11—C10—C9	122.7 (5)	C25—C26—Cl3	117.9 (5)
C11—C10—Cl2B	110.7 (7)	C26—C27—C28	119.7 (5)
C9—C10—Cl2B	121.7 (5)	C26—C27—H27	120.2
C11—C10—Cl2A	120.3 (4)	C28—C27—H27	120.2
C9—C10—Cl2A	116.9 (5)	C27—C28—C29	121.0 (6)
C10—C11—C12	118.0 (4)	C27—C28—H28	119.5
C10—C11—H11	121.0	C29—C28—H28	119.5
C12—C11—H11	121.0	C24—C29—C28	119.5 (6)
C13—C12—C11	120.5 (5)	C24—C29—H29	120.2
C13—C12—H12	119.8	C28—C29—H29	120.2
C11—C12—H12	119.8	C23—C30—C31	114.6 (3)
C8—C13—C12	120.7 (4)	C23—C30—H30A	108.6
C8—C13—H13	119.7	C31—C30—H30A	108.6
C12—C13—H13	119.7	C23—C30—H30B	108.6
C7—C14—C15	110.9 (4)	C31—C30—H30B	108.6
C7—C14—H14A	109.5	H30A—C30—H30B	107.6
C15—C14—H14A	109.5	C30—C31—C32	111.9 (3)
C7—C14—H14B	109.5	C30—C31—H31A	109.2
C15—C14—H14B	109.5	C32—C31—H31A	109.2
H14A—C14—H14B	108.1	C30—C31—H31B	109.2
C14—C15—C16	107.3 (7)	C32—C31—H31B	109.2
C14—C15—H15A	110.3	H31A—C31—H31B	107.9
C16—C15—H15A	110.3	C32ii—C32—C31	112.6 (4)
C14—C15—H15B	110.3	C32ii—C32—H32A	109.1
C16—C15—H15B	110.3	C31—C32—H32A	109.1
H15A—C15—H15B	108.5	C32ii—C32—H32B	109.1
C16i—C16—C15	120.0 (11)	C31—C32—H32B	109.1
C16i—C16—H16A	107.3	H32A—C32—H32B	107.8
C15—C16—H16A	107.3	C7—N1—C1	120.8 (3)
C16i—C16—H16B	107.3	C7—N2—C8	128.9 (3)
C15—C16—H16B	107.3	C7—N2—H2A	115.6
H16A—C16—H16B	106.9	C8—N2—H2A	115.6
C18—C17—C22	118.2 (4)	C23—N3—C17	120.5 (3)
C18—C17—N3	120.9 (4)	C23—N4—C24	125.8 (3)
C22—C17—N3	120.8 (4)	C23—N4—H4A	117.1
C17—C18—C19	119.2 (4)	C24—N4—H4A	117.1
C6—C1—C2—C3	0.6 (6)	C19—C20—C21—C22	−6.4 (10)
N1—C1—C2—C3	−173.3 (3)	C18—C17—C22—C21	0.1 (8)
C1—C2—C3—C4	0.1 (6)	N3—C17—C22—C21	−176.5 (5)
C1—C2—C3—Cl1	−179.4 (3)	C20—C21—C22—C17	3.0 (10)
C2—C3—C4—C5	−0.8 (7)	C29—C24—C25—C26	0.6 (6)
Cl1—C3—C4—C5	178.8 (4)	N4—C24—C25—C26	176.4 (4)
C3—C4—C5—C6	0.7 (8)	C24—C25—C26—C27	0.7 (7)
C4—C5—C6—C1	0.0 (8)	C24—C25—C26—Cl3	−178.5 (3)
C2—C1—C6—C5	−0.6 (6)	C25—C26—C27—C28	−0.9 (9)
N1—C1—C6—C5	173.3 (4)	Cl3—C26—C27—C28	178.3 (5)
C13—C8—C9—C10	−0.1 (6)	C26—C27—C28—C29	−0.3 (10)
N2—C8—C9—C10	−178.0 (4)	C25—C24—C29—C28	−1.7 (8)
C8—C9—C10—C11	−1.3 (8)	N4—C24—C29—C28	−177.3 (5)
C8—C9—C10—Cl2B	−154.1 (14)	C27—C28—C29—C24	1.6 (10)
C8—C9—C10—Cl2A	175.5 (6)	N3—C23—C30—C31	128.1 (4)
C9—C10—C11—C12	1.9 (9)	N4—C23—C30—C31	−55.7 (4)
Cl2B—C10—C11—C12	157.4 (13)	C23—C30—C31—C32	175.8 (3)
Cl2A—C10—C11—C12	−174.8 (7)	C30—C31—C32—C32ii	−174.4 (4)
C10—C11—C12—C13	−1.1 (9)	N2—C7—N1—C1	172.6 (4)
C9—C8—C13—C12	0.7 (7)	C14—C7—N1—C1	−12.8 (6)
N2—C8—C13—C12	178.8 (4)	C2—C1—N1—C7	−80.4 (5)
C11—C12—C13—C8	−0.1 (8)	C6—C1—N1—C7	105.8 (5)
N1—C7—C14—C15	−87.0 (6)	N1—C7—N2—C8	−8.7 (6)
N2—C7—C14—C15	88.0 (5)	C14—C7—N2—C8	176.2 (4)
C7—C14—C15—C16	170.0 (5)	C13—C8—N2—C7	153.9 (4)
C14—C15—C16—C16i	122.4 (4)	C9—C8—N2—C7	−28.1 (6)
C22—C17—C18—C19	0.4 (8)	N4—C23—N3—C17	172.8 (3)
N3—C17—C18—C19	177.1 (5)	C30—C23—N3—C17	−11.2 (6)
C17—C18—C19—C20	−4.2 (9)	C18—C17—N3—C23	103.0 (5)
C17—C18—C19—Cl4A	169.8 (5)	C22—C17—N3—C23	−80.4 (6)
C17—C18—C19—Cl4B	−151.6 (8)	N3—C23—N4—C24	−14.6 (6)
C18—C19—C20—C21	7.1 (10)	C30—C23—N4—C24	169.0 (3)
Cl4A—C19—C20—C21	−166.8 (6)	C29—C24—N4—C23	−41.1 (6)
Cl4B—C19—C20—C21	155.6 (9)	C25—C24—N4—C23	143.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3	0.86	2.24	3.049 (4)	157
N4—H4A···N1iii	0.86	2.23	3.072 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N3	0.86	2.24	3.049 (4)	157
N4—H4A⋯N1i	0.86	2.23	3.072 (4)	168

Symmetry code: (i) .