N,N′-Bis(3-chloro­phen­yl)malonamide

Rodrigues, V.Z.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811031333

N,N′-Bis(3-chlorophenyl)malonamide

V. Z. Rodrigues, S. Foro and B. T. Gowda

The asymmetric unit of the title compound, C₁₅H₁₂Cl₂N₂O₂, contains two independent molecules. In both independent molecules, 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 molecules, 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 molecules. In the crystal, molecules are linked into a chain by intermolecular N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811031333/nc2242sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811031333/nc2242Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811031333/nc2242Isup3.cml Supplementary material

CCDC reference: 845338

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.047
wR factor = 0.114
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......      0.949

Author Response: The compound is a weak scatterer with low intensity at high theta value. Low fraction of unique data is above the 2 sigma level (49.4 \%).


Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.18
           From the CIF: _diffrn_reflns_theta_full          25.18
           From the CIF: _reflns_number_total               5164
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5436
           Completeness (_total/calc)             95.00%
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C10    -C15           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0048 Ang
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          6
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.599        272

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The amide and sulfonamide moieties are important constituents of many biologically significant compounds. As a part of studying the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004, Gowda et al., 2010, Saraswathi et al., 2011); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloro-arylsulfonamides (Gowda & Kumar, 2003), in the present work, the structure of N,N-bis(3-chlorophenyl)-malonamide (I) has been determined (Fig.1). The asymmetric unit of (I) contains two independent molecules. The conformations of all the N—H, C=O and C—H bonds in the central amide and aliphatic segments are anti to their adjacent bonds. Further, in both of the independent molecules, the N—H bonds in the amide fragments are anti to the meta-chloro groups in one of the adjacent benzene rings and syn to the meta-chloro group in the other, in contrast to the syn conformations of the N—H bonds with respect to the meta-methyl groups in the adjacent benzene rings of N,N-bis(3-methylphenyl)-malonamide (II)(Gowda et al., 2010) and anti conformations of the N—H bonds with respect to the meta-chloro groups in N,N- bis(3-chlorophenyl)-succinamide (III) (Saraswathi et al., 2011).

In the geometry of the molecule, each amide group is almost coplanar with the adjacent phenyl rings, as indicated by the dihedral angles of 10.5 (2)°, 8.7 (2)° (molecule 1) and 9.0 (2)°, 9.6 (2)° (molecule 2), compared to the value of 9.2 (2)° in (II). The planes of amide groups are inclined at angles of 83.4 (1)° (molecule 1) and 87.4 (1)° (molecule 2), in contrast to the value of 68.5 (1)° in (II). The phenyl rings of the two molecules make a dihedral angle of 21.5 (1)°.

In the crystal, the molecules are linked into chains by intermolecular N–H···O hydrogen bonding as shown in Fig. 2 (Table 1) .

Related literature top

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 top

Malonic acid (0.3 mol) in dichloromethane (30 ml) was treated with m-chloroaniline (0.6 mol) in dichloromethane (30 ml), dropwise with stirring. The resulting mixture was stirred for 3 hrs and kept aside for 12 hrs for the completion of reaction and evaporation of the solvent, dichloromethane. The product obtained was added to crushed ice to obtain the precipitate. The latter was thoroughly washed with water and then with saturated sodium bicarbonate solution and washed again with water. It was then given a wash with 2 N HCl. It was again washed with water, filtered, dried and recrystallized to the constant melting point from ethanol.

Prism like colorless single crystals of the title compound used in X-ray diffraction studies were obtained by a slow evaporation of its ehanolic solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal structure of (I) with hydrogen bonding shown as dashed lines.

N,N'-Bis(3-chlorophenyl)malonamide top

Crystal data top

C₁₅H₁₂Cl₂N₂O₂	F(000) = 1328
M_r = 323.17	D_x = 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

Data collection top

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 monochromator	R_int = 0.027
Rotation method data acquisition using ω and ϕ scans	θ_max = 25.2°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→12
T_min = 0.819, T_max = 0.903	k = −19→18
12003 measured reflections	l = −20→15

Refinement top

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(F_o²) + (0.0536P)²] where P = (F_o² + 2F_c²)/3
5164 reflections	(Δ/σ)_max < 0.001
391 parameters	Δρ_max = 0.25 e Å⁻³
4 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₅H₁₂Cl₂N₂O₂	V = 3025.0 (3) Å³
M_r = 323.17	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9209 (8) Å	µ = 0.43 mm⁻¹
b = 16.416 (1) Å	T = 293 K
c = 17.490 (1) Å	0.48 × 0.28 × 0.24 mm
β = 105.260 (6)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5164 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2767 reflections with I > 2σ(I)
T_min = 0.819, T_max = 0.903	R_int = 0.027
12003 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	4 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.25 e Å⁻³
5164 reflections	Δρ_min = −0.29 e Å⁻³
391 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂Cl₂N₂O₂
M_r	323.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.9209 (8), 16.416 (1), 17.490 (1)
β (°)	105.260 (6)
V (Å³)	3025.0 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.48 × 0.28 × 0.24

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.819, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	12003, 5164, 2767
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.114, 0.96
No. of reflections	5164
No. of parameters	391
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.29

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).