N,N'-Bis(3-chloro-phen-yl)malonamide.

The asymmetric unit of the title compound, C(15)H(12)Cl(2)N(2)O(2), contains two independent mol-ecules. In both independent mol-ecules, the N-H bond in one of the amide fragments is anti to the meta-chloro group of the adjacent benzene ring and that in the other amide group is syn to the other meta-chloro group. Furthermore, in both mol-ecules, each amide group is almost coplanar with the adjacent phenyl ring, making dihedral angles of 10.5 (2) and 8.7 (2)° in one molecule and 9.0 (2) and 9.6 (2)° in the other. The planes of the amide groups are inclined at dihedral angles of 83.4 (1) and 87.4 (1)° in the two mol-ecules. In the crystal, mol-ecules are linked into a chain by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004 ▶); Gowda et al. (2010 ▶); Saraswathi et al. (2011 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and on N-chloro-aryl­sulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C15H12Cl2N2O2

M = 323.17

Monoclinic,

a = 10.9209 (8) Å

b = 16.416 (1) Å

c = 17.490 (1) Å

β = 105.260 (6)°

V = 3025.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.48 × 0.28 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.819, T max = 0.903

12003 measured reflections

5164 independent reflections

2767 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.114

S = 0.96

5164 reflections

391 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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 datablock(s) I, global. DOI: 10.1107/S1600536811031333/nc2242sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031333/nc2242Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031333/nc2242Isup3.cml

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

C15H12Cl2N2O2	F(000) = 1328
Mr = 323.17	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2892 reflections
a = 10.9209 (8) Å	θ = 2.7–27.8°
b = 16.416 (1) Å	µ = 0.43 mm−1
c = 17.490 (1) Å	T = 293 K
β = 105.260 (6)°	Prism, colourless
V = 3025.0 (3) Å3	0.48 × 0.28 × 0.24 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5164 independent reflections
Radiation source: fine-focus sealed tube	2767 reflections with I > 2σ(I)
graphite	Rint = 0.027
Rotation method data acquisition using ω and φ scans	θmax = 25.2°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→12
Tmin = 0.819, Tmax = 0.903	k = −19→18
12003 measured reflections	l = −20→15

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0536P)2] where P = (Fo2 + 2Fc2)/3
5164 reflections	(Δ/σ)max < 0.001
391 parameters	Δρmax = 0.25 e Å−3
4 restraints	Δρmin = −0.29 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
Cl1	0.08136 (11)	0.24962 (7)	−0.09253 (6)	0.1097 (4)
Cl2	1.03780 (9)	0.56633 (6)	0.20849 (5)	0.0876 (3)
O1	0.42401 (19)	0.33751 (13)	0.14639 (11)	0.0623 (6)
O2	0.6972 (2)	0.21642 (13)	0.22591 (12)	0.0640 (6)
N1	0.3525 (2)	0.22476 (16)	0.19545 (14)	0.0479 (7)
H1N	0.375 (3)	0.1947 (15)	0.2358 (12)	0.058*
N2	0.7334 (2)	0.35055 (16)	0.25539 (13)	0.0464 (6)
H2N	0.702 (2)	0.3931 (13)	0.2729 (15)	0.056*
C1	0.2485 (3)	0.20088 (18)	0.13298 (19)	0.0495 (8)
C2	0.2199 (3)	0.23552 (19)	0.05850 (18)	0.0541 (8)
H2	0.2692	0.2777	0.0472	0.065*
C3	0.1173 (3)	0.2066 (2)	0.0013 (2)	0.0684 (10)
C4	0.0426 (3)	0.1446 (3)	0.0162 (3)	0.0912 (13)
H4	−0.0271	0.1261	−0.0229	0.109*
C5	0.0740 (4)	0.1104 (3)	0.0908 (3)	0.1005 (14)
H5	0.0257	0.0675	0.1018	0.121*
C6	0.1748 (3)	0.1384 (2)	0.1490 (2)	0.0751 (10)
H6	0.1935	0.1154	0.1993	0.090*
C7	0.4340 (3)	0.28635 (19)	0.19877 (17)	0.0454 (8)
C8	0.5425 (3)	0.28865 (18)	0.27290 (15)	0.0506 (8)
H8A	0.5345	0.2441	0.3077	0.061*
H8B	0.5408	0.3394	0.3009	0.061*
C9	0.6661 (3)	0.2813 (2)	0.24981 (15)	0.0459 (8)
C10	0.8452 (3)	0.3654 (2)	0.23050 (15)	0.0439 (7)
C11	0.8857 (3)	0.4459 (2)	0.23304 (15)	0.0504 (8)
H11	0.8418	0.4864	0.2521	0.060*
C12	0.9902 (3)	0.4656 (2)	0.20745 (16)	0.0574 (9)
C13	1.0551 (3)	0.4076 (3)	0.1792 (2)	0.0786 (11)
H13	1.1260	0.4212	0.1618	0.094*
C14	1.0143 (4)	0.3290 (3)	0.1768 (2)	0.0896 (12)
H14	1.0584	0.2893	0.1570	0.108*
C15	0.9102 (3)	0.3058 (2)	0.20266 (19)	0.0660 (9)
H15	0.8852	0.2515	0.2012	0.079*
Cl3	0.23604 (9)	−0.20233 (6)	0.53548 (6)	0.0919 (4)
Cl4	0.20833 (9)	0.00640 (8)	−0.10657 (5)	0.1024 (4)
O3	0.4176 (2)	0.11744 (14)	0.33566 (12)	0.0667 (6)
O4	0.4030 (2)	−0.01860 (13)	0.18439 (11)	0.0593 (6)
N3	0.4492 (2)	−0.01203 (14)	0.38243 (12)	0.0413 (6)
H3N	0.488 (2)	−0.0561 (13)	0.3785 (14)	0.050*
N4	0.5293 (2)	0.08006 (14)	0.15599 (13)	0.0438 (6)
H4N	0.586 (2)	0.1142 (14)	0.1768 (14)	0.053*
C16	0.3616 (3)	−0.01776 (19)	0.42933 (13)	0.0394 (7)
C17	0.3449 (3)	−0.09478 (19)	0.45764 (15)	0.0465 (8)
H17	0.3916	−0.1387	0.4470	0.056*
C18	0.2586 (3)	−0.1056 (2)	0.50165 (16)	0.0546 (8)
C19	0.1891 (3)	−0.0411 (2)	0.51849 (17)	0.0622 (10)
H19	0.1308	−0.0489	0.5481	0.075*
C20	0.2076 (3)	0.0342 (2)	0.49082 (17)	0.0622 (9)
H20	0.1612	0.0780	0.5022	0.075*
C21	0.2933 (3)	0.04743 (19)	0.44636 (15)	0.0502 (8)
H21	0.3049	0.0994	0.4282	0.060*
C22	0.4710 (3)	0.0515 (2)	0.33970 (15)	0.0460 (8)
C23	0.5658 (3)	0.03563 (18)	0.29160 (14)	0.0490 (8)
H23A	0.6115	−0.0146	0.3087	0.059*
H23B	0.6266	0.0799	0.2987	0.059*
C24	0.4916 (3)	0.02930 (19)	0.20509 (16)	0.0448 (7)
C25	0.4727 (3)	0.09431 (18)	0.07396 (15)	0.0429 (7)
C26	0.3772 (3)	0.04626 (19)	0.02923 (17)	0.0506 (8)
H26	0.3471	0.0016	0.0515	0.061*
C27	0.3274 (3)	0.0660 (2)	−0.04923 (18)	0.0600 (9)
C28	0.3689 (3)	0.1322 (3)	−0.08368 (19)	0.0762 (11)
H28	0.3323	0.1451	−0.1365	0.091*
C29	0.4653 (4)	0.1787 (2)	−0.03847 (19)	0.0762 (11)
H29	0.4949	0.2235	−0.0609	0.091*
C30	0.5188 (3)	0.15961 (19)	0.04018 (17)	0.0575 (9)
H30	0.5856	0.1906	0.0702	0.069*

	U11	U22	U33	U12	U13	U23
Cl1	0.1013 (8)	0.1303 (10)	0.0822 (7)	0.0026 (7)	−0.0028 (6)	0.0018 (6)
Cl2	0.0953 (7)	0.0791 (8)	0.0886 (7)	−0.0246 (6)	0.0245 (5)	0.0113 (5)
O1	0.0801 (16)	0.0477 (15)	0.0581 (13)	−0.0170 (12)	0.0161 (11)	0.0143 (11)
O2	0.0779 (16)	0.0394 (15)	0.0806 (15)	−0.0013 (12)	0.0314 (12)	−0.0179 (12)
N1	0.0533 (17)	0.0379 (19)	0.0581 (17)	0.0049 (14)	0.0244 (14)	0.0116 (13)
N2	0.0567 (17)	0.0329 (19)	0.0520 (15)	0.0060 (14)	0.0183 (12)	−0.0084 (12)
C1	0.0450 (19)	0.033 (2)	0.076 (2)	0.0052 (16)	0.0267 (17)	0.0051 (17)
C2	0.049 (2)	0.045 (2)	0.072 (2)	−0.0011 (17)	0.0235 (16)	−0.0012 (18)
C3	0.057 (2)	0.059 (3)	0.084 (3)	0.006 (2)	0.0103 (19)	−0.004 (2)
C4	0.053 (2)	0.074 (3)	0.134 (4)	−0.014 (2)	0.002 (2)	−0.015 (3)
C5	0.070 (3)	0.074 (3)	0.155 (4)	−0.022 (2)	0.025 (3)	0.024 (3)
C6	0.059 (2)	0.056 (3)	0.111 (3)	−0.011 (2)	0.024 (2)	0.021 (2)
C7	0.055 (2)	0.033 (2)	0.0572 (19)	0.0008 (17)	0.0297 (16)	0.0018 (16)
C8	0.070 (2)	0.040 (2)	0.0474 (17)	−0.0036 (17)	0.0264 (15)	−0.0015 (15)
C9	0.059 (2)	0.040 (2)	0.0379 (16)	0.0043 (19)	0.0130 (14)	−0.0023 (15)
C10	0.0422 (18)	0.046 (2)	0.0416 (16)	0.0050 (17)	0.0085 (13)	−0.0045 (15)
C11	0.055 (2)	0.049 (2)	0.0460 (17)	0.0058 (18)	0.0122 (14)	−0.0066 (15)
C12	0.057 (2)	0.063 (3)	0.0501 (18)	−0.0036 (19)	0.0098 (15)	0.0052 (17)
C13	0.066 (3)	0.086 (3)	0.093 (3)	−0.003 (3)	0.037 (2)	−0.001 (2)
C14	0.076 (3)	0.082 (4)	0.129 (3)	0.019 (3)	0.058 (2)	−0.013 (3)
C15	0.067 (2)	0.046 (2)	0.091 (2)	0.0126 (19)	0.0323 (19)	−0.0072 (19)
Cl3	0.0972 (8)	0.0803 (8)	0.1077 (7)	−0.0137 (6)	0.0441 (6)	0.0323 (6)
Cl4	0.0661 (6)	0.1521 (11)	0.0806 (6)	−0.0219 (6)	0.0044 (5)	−0.0187 (6)
O3	0.0951 (17)	0.0433 (16)	0.0743 (14)	0.0199 (13)	0.0445 (12)	0.0203 (11)
O4	0.0681 (15)	0.0522 (16)	0.0596 (13)	−0.0158 (13)	0.0202 (11)	0.0084 (11)
N3	0.0560 (16)	0.0297 (17)	0.0407 (12)	0.0078 (13)	0.0174 (11)	0.0041 (12)
N4	0.0558 (17)	0.0353 (18)	0.0450 (15)	−0.0108 (12)	0.0218 (12)	−0.0038 (12)
C16	0.0478 (18)	0.041 (2)	0.0290 (14)	0.0003 (16)	0.0085 (12)	−0.0003 (14)
C17	0.0533 (19)	0.042 (2)	0.0432 (16)	0.0020 (16)	0.0102 (14)	0.0024 (15)
C18	0.056 (2)	0.059 (3)	0.0485 (17)	−0.0079 (18)	0.0140 (15)	0.0105 (16)
C19	0.057 (2)	0.082 (3)	0.0536 (19)	−0.006 (2)	0.0251 (15)	−0.002 (2)
C20	0.067 (2)	0.064 (3)	0.063 (2)	0.0073 (19)	0.0289 (17)	−0.0031 (19)
C21	0.061 (2)	0.043 (2)	0.0477 (17)	0.0008 (17)	0.0171 (15)	−0.0021 (15)
C22	0.057 (2)	0.040 (2)	0.0411 (16)	0.0048 (18)	0.0137 (14)	0.0046 (15)
C23	0.0547 (19)	0.047 (2)	0.0492 (17)	0.0036 (16)	0.0200 (14)	0.0108 (15)
C24	0.0523 (19)	0.038 (2)	0.0508 (18)	0.0014 (17)	0.0262 (15)	0.0021 (15)
C25	0.0553 (19)	0.040 (2)	0.0403 (17)	−0.0007 (16)	0.0255 (14)	−0.0032 (15)
C26	0.055 (2)	0.050 (2)	0.0515 (19)	0.0012 (17)	0.0233 (15)	0.0010 (16)
C27	0.0464 (19)	0.082 (3)	0.055 (2)	−0.0023 (18)	0.0182 (16)	−0.0085 (19)
C28	0.079 (3)	0.111 (4)	0.0435 (19)	0.002 (2)	0.0246 (19)	0.009 (2)
C29	0.097 (3)	0.088 (3)	0.052 (2)	−0.015 (2)	0.0347 (19)	0.011 (2)
C30	0.076 (2)	0.054 (2)	0.0502 (19)	−0.0157 (19)	0.0300 (16)	−0.0015 (17)

Cl1—C3	1.734 (3)	Cl3—C18	1.734 (3)
Cl2—C12	1.731 (3)	Cl4—C27	1.723 (3)
O1—C7	1.226 (3)	O3—C22	1.223 (3)
O2—C9	1.224 (3)	O4—C24	1.225 (3)
N1—C7	1.338 (3)	N3—C22	1.340 (3)
N1—C1	1.409 (4)	N3—C16	1.418 (3)
N1—H1N	0.843 (16)	N3—H3N	0.853 (16)
N2—C9	1.343 (4)	N4—C24	1.337 (3)
N2—C10	1.421 (4)	N4—C25	1.424 (3)
N2—H2N	0.867 (17)	N4—H4N	0.845 (16)
C1—C6	1.377 (4)	C16—C21	1.381 (4)
C1—C2	1.380 (4)	C16—C17	1.387 (3)
C2—C3	1.376 (4)	C17—C18	1.376 (4)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.372 (5)	C18—C19	1.379 (4)
C4—C5	1.378 (5)	C19—C20	1.363 (4)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.367 (5)	C20—C21	1.383 (4)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.509 (4)	C22—C23	1.518 (4)
C8—C9	1.513 (4)	C23—C24	1.520 (4)
C8—H8A	0.9700	C23—H23A	0.9700
C8—H8B	0.9700	C23—H23B	0.9700
C10—C15	1.372 (4)	C25—C26	1.376 (4)
C10—C11	1.391 (4)	C25—C30	1.382 (3)
C11—C12	1.370 (4)	C26—C27	1.375 (4)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.356 (4)	C27—C28	1.376 (4)
C13—C14	1.362 (5)	C28—C29	1.370 (4)
C13—H13	0.9300	C28—H28	0.9300
C14—C15	1.383 (5)	C29—C30	1.382 (4)
C14—H14	0.9300	C29—H29	0.9300
C15—H15	0.9300	C30—H30	0.9300
C7—N1—C1	129.4 (3)	C22—N3—C16	128.3 (2)
C7—N1—H1N	111 (2)	C22—N3—H3N	116.7 (18)
C1—N1—H1N	119 (2)	C16—N3—H3N	114.8 (18)
C9—N2—C10	128.4 (3)	C24—N4—C25	128.6 (2)
C9—N2—H2N	116.6 (19)	C24—N4—H4N	116.9 (18)
C10—N2—H2N	114.8 (19)	C25—N4—H4N	113.6 (18)
C6—C1—C2	120.0 (3)	C21—C16—C17	120.0 (3)
C6—C1—N1	116.4 (3)	C21—C16—N3	123.9 (3)
C2—C1—N1	123.6 (3)	C17—C16—N3	116.0 (3)
C3—C2—C1	118.9 (3)	C18—C17—C16	119.4 (3)
C3—C2—H2	120.5	C18—C17—H17	120.3
C1—C2—H2	120.5	C16—C17—H17	120.3
C4—C3—C2	121.9 (3)	C17—C18—C19	121.1 (3)
C4—C3—Cl1	119.0 (3)	C17—C18—Cl3	119.3 (3)
C2—C3—Cl1	119.1 (3)	C19—C18—Cl3	119.6 (3)
C3—C4—C5	118.0 (4)	C20—C19—C18	118.7 (3)
C3—C4—H4	121.0	C20—C19—H19	120.6
C5—C4—H4	121.0	C18—C19—H19	120.6
C6—C5—C4	121.3 (4)	C19—C20—C21	121.8 (3)
C6—C5—H5	119.4	C19—C20—H20	119.1
C4—C5—H5	119.4	C21—C20—H20	119.1
C5—C6—C1	119.9 (4)	C20—C21—C16	118.9 (3)
C5—C6—H6	120.1	C20—C21—H21	120.5
C1—C6—H6	120.1	C16—C21—H21	120.5
O1—C7—N1	123.9 (3)	O3—C22—N3	124.7 (3)
O1—C7—C8	121.3 (3)	O3—C22—C23	120.3 (3)
N1—C7—C8	114.8 (3)	N3—C22—C23	115.0 (3)
C7—C8—C9	108.8 (2)	C22—C23—C24	107.5 (2)
C7—C8—H8A	109.9	C22—C23—H23A	110.2
C9—C8—H8A	109.9	C24—C23—H23A	110.2
C7—C8—H8B	109.9	C22—C23—H23B	110.2
C9—C8—H8B	109.9	C24—C23—H23B	110.2
H8A—C8—H8B	108.3	H23A—C23—H23B	108.5
O2—C9—N2	124.4 (3)	O4—C24—N4	124.2 (3)
O2—C9—C8	120.5 (3)	O4—C24—C23	120.7 (2)
N2—C9—C8	115.0 (3)	N4—C24—C23	115.1 (3)
C15—C10—C11	120.0 (3)	C26—C25—C30	120.6 (3)
C15—C10—N2	123.6 (3)	C26—C25—N4	122.8 (3)
C11—C10—N2	116.4 (3)	C30—C25—N4	116.6 (3)
C12—C11—C10	119.9 (3)	C25—C26—C27	118.3 (3)
C12—C11—H11	120.0	C25—C26—H26	120.9
C10—C11—H11	120.0	C27—C26—H26	120.9
C13—C12—C11	120.9 (3)	C28—C27—C26	122.3 (3)
C13—C12—Cl2	119.3 (3)	C28—C27—Cl4	118.6 (3)
C11—C12—Cl2	119.7 (3)	C26—C27—Cl4	119.1 (3)
C12—C13—C14	118.6 (3)	C29—C28—C27	118.6 (3)
C12—C13—H13	120.7	C29—C28—H28	120.7
C14—C13—H13	120.7	C27—C28—H28	120.7
C13—C14—C15	122.8 (4)	C28—C29—C30	120.5 (3)
C13—C14—H14	118.6	C28—C29—H29	119.8
C15—C14—H14	118.6	C30—C29—H29	119.8
C10—C15—C14	117.8 (3)	C25—C30—C29	119.7 (3)
C10—C15—H15	121.1	C25—C30—H30	120.1
C14—C15—H15	121.1	C29—C30—H30	120.1
C7—N1—C1—C6	−174.9 (3)	C22—N3—C16—C21	−8.5 (4)
C7—N1—C1—C2	6.2 (5)	C22—N3—C16—C17	170.5 (3)
C6—C1—C2—C3	0.0 (4)	C21—C16—C17—C18	1.0 (4)
N1—C1—C2—C3	178.9 (3)	N3—C16—C17—C18	−178.1 (2)
C1—C2—C3—C4	0.1 (5)	C16—C17—C18—C19	−0.4 (4)
C1—C2—C3—Cl1	−179.7 (2)	C16—C17—C18—Cl3	178.88 (19)
C2—C3—C4—C5	−0.7 (6)	C17—C18—C19—C20	−0.2 (4)
Cl1—C3—C4—C5	179.0 (3)	Cl3—C18—C19—C20	−179.5 (2)
C3—C4—C5—C6	1.4 (6)	C18—C19—C20—C21	0.2 (5)
C4—C5—C6—C1	−1.3 (6)	C19—C20—C21—C16	0.3 (4)
C2—C1—C6—C5	0.6 (5)	C17—C16—C21—C20	−0.9 (4)
N1—C1—C6—C5	−178.4 (3)	N3—C16—C21—C20	178.1 (3)
C1—N1—C7—O1	5.5 (5)	C16—N3—C22—O3	1.3 (5)
C1—N1—C7—C8	−174.1 (3)	C16—N3—C22—C23	−176.1 (2)
O1—C7—C8—C9	−60.1 (4)	O3—C22—C23—C24	−70.9 (3)
N1—C7—C8—C9	119.5 (3)	N3—C22—C23—C24	106.7 (3)
C10—N2—C9—O2	5.1 (5)	C25—N4—C24—O4	5.2 (5)
C10—N2—C9—C8	−172.8 (2)	C25—N4—C24—C23	−173.6 (3)
C7—C8—C9—O2	−71.9 (3)	C22—C23—C24—O4	−54.1 (4)
C7—C8—C9—N2	106.1 (3)	C22—C23—C24—N4	124.7 (3)
C9—N2—C10—C15	−6.8 (5)	C24—N4—C25—C26	−10.5 (4)
C9—N2—C10—C11	171.2 (3)	C24—N4—C25—C30	169.7 (3)
C15—C10—C11—C12	0.3 (4)	C30—C25—C26—C27	−1.3 (4)
N2—C10—C11—C12	−177.8 (2)	N4—C25—C26—C27	179.0 (3)
C10—C11—C12—C13	0.2 (4)	C25—C26—C27—C28	−0.8 (4)
C10—C11—C12—Cl2	178.4 (2)	C25—C26—C27—Cl4	179.7 (2)
C11—C12—C13—C14	−0.1 (5)	C26—C27—C28—C29	1.6 (5)
Cl2—C12—C13—C14	−178.3 (3)	Cl4—C27—C28—C29	−178.8 (3)
C12—C13—C14—C15	−0.6 (6)	C27—C28—C29—C30	−0.4 (5)
C11—C10—C15—C14	−0.9 (5)	C26—C25—C30—C29	2.5 (4)
N2—C10—C15—C14	177.0 (3)	N4—C25—C30—C29	−177.8 (3)
C13—C14—C15—C10	1.1 (6)	C28—C29—C30—C25	−1.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.84 (2)	2.11 (2)	2.950 (3)	176 (3)
N2—H2N···O4i	0.87 (2)	2.11 (2)	2.961 (3)	169 (3)
N3—H3N···O1ii	0.85 (2)	2.09 (2)	2.939 (3)	173 (2)
N4—H4N···O2	0.85 (2)	2.12 (2)	2.947 (3)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.84 (2)	2.11 (2)	2.950 (3)	176 (3)
N2—H2N⋯O4i	0.87 (2)	2.11 (2)	2.961 (3)	169 (3)
N3—H3N⋯O1ii	0.85 (2)	2.09 (2)	2.939 (3)	173 (2)
N4—H4N⋯O2	0.85 (2)	2.12 (2)	2.947 (3)	168 (3)

Symmetry codes: (i) ; (ii) .