N-(2,6-Dichloro­phen­yl)benzamide

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S160053680800305X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o540

doi:10.1107/S160053680800305X

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N-(2,6-Dichlorophenyl)benzamide

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b B. P. Sowmya ^a and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri-574 199, Mangalore, India, ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 15 January 2008; accepted 28 January 2008; online 30 January 2008)

The conformation of the N—H and C=O bonds in the structure of the title compound (N26DCPBA), C₁₃H₉Cl₂NO, are anti to each other, similar to that observed in N-phenylbenzamide (NPBA), N-(2-chlorophenyl)benzamide (N2CPBA), N-(2,3-dichlorophenyl)benzamide (N23DCPBA) and other benzanilides. The asymmetric unit of N26DCPBA contains two molecules. The bond parameters in N26DCPBA are similar to those in NPBA, N2CPBA, N23DCPBA and other benzanilides. The amide group, –NHCO–, makes a dihedral angle of 30.8 (1)° with the benzoyl ring in the first molecule and 35.1 (2)° in the second molecule of the asymmetric unit. The dihedral angle between the two benzene rings (benzoyl and aniline) is 56.8 (1)° in the first molecule and 59.1 (1)° in the second molecule. N—H⋯O hydrogen bonds give rise to infinite chains running along the a axis of the crystal structure.

Related literature

For related literature, see: Gowda et al. (2003 , 2007a ,b ,c , 2008 ).

Experimental

Crystal data

C₁₃H₉Cl₂NO
M_r = 266.11
Monoclinic, P 2₁ /c
a = 10.0431 (2) Å
b = 13.7150 (3) Å
c = 18.4585 (4) Å
β = 93.623 (2)°
V = 2537.41 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 295 (2) K
0.26 × 0.24 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer
Absorption correction: analytical [(Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995 )] T_min = 0.882, T_max = 0.904
54956 measured reflections
4956 independent reflections
3810 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.127
S = 1.10
4956 reflections
314 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.860 (19)	2.09 (2)	2.9035 (18)	158 (2)
N2—H2N⋯O1ⁱ	0.843 (18)	2.060 (19)	2.8831 (18)	165.1 (19)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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, 2002 ); software used to prepare material for publication: SHELXL97], PLATON (Spek, 2003 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800305X/om2209sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800305X/om2209Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of N-(2,6-dichlorophenyl)-benzamide (N26DCPBA) has been determined to explore the effect of substituents on the structure of N-aromatic amides (Gowda et al., 2003,2007a,b,c,2008). The conformation of the N—H and C=O bonds in the structure of N26DCPBA (Fig.1) are anti to each other, similar to that observed in N-(phenyl)-benzamide (NPBA)(Gowda et al., 2003), N-(2-chlorophenyl)-benzamide (N2CPBA), N-(2,3-dichlorophenyl)-benzamide (N23DCPBA) and other benzanilides(Gowda et al., 2007a,b,c, 2008). The title compound crystallizes in the space group P21/c, with two molecules in the asymmetric unit. The bond parameters in N26DCPBA are similar to those in NPBA, N2CPBA, N23DCPBA and other benzanilides. The amide group –NHCO– has the dihedral angle of 30.8 (1)° with the benzoyl ring in the first molecule and 35.1 (2)° in the second molecule of the asymmetric unit. The dihedral angle between the two benzene rings (benzoyl and aniline) is 56.8 (1)° in the first molecule and 59.1 (1)° in the second molecule. One-dimensional chains of N26DCPBA along the base vector [1 0 0] formed by hydrogen bonds N1–H1N···O2(i) and N2–H2N···O1 (Table 1) as viewed down the b axis is shown in Fig.2. Symmetry code (i): x + 1,y,z.

Related literature top

For related literature, see: Gowda et al. (2003, 2007a,b,c, 2008).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CrysAlis CCD, Oxford Diffraction, 2007; cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Numbers of the C atoms in the second molecule are increased by 20. Displacement ellipsoids are drawn at the 30% probability level. The hydrogen bond N2—H2N···O1 is shown as a dashed line.
	Fig. 2. Crystal structure of the title compound viewed down the b axis. One-dimensional chains along the base vector [1 0 0] are formed by hydrogen bonds N1–H1N···O2 and N2–H2N···O1(i). Symmetry code (i): x + 1,y,z. H atoms not involved in hydrogen bonding are omitted.

N-(2,6-Dichlorophenyl)benzamide top

Crystal data top

C₁₃H₉Cl₂NO	F(000) = 1088
M_r = 266.11	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 24495 reflections
a = 10.0431 (2) Å	θ = 3.1–29.5°
b = 13.7150 (3) Å	µ = 0.49 mm⁻¹
c = 18.4585 (4) Å	T = 295 K
β = 93.623 (2)°	Block, colorless
V = 2537.41 (9) Å³	0.26 × 0.24 × 0.21 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur System diffractometer	4956 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3810 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.434 pixels mm^-1	θ_max = 26.0°, θ_min = 5.1°
ϕ scans, and ω scans with κ offsets	h = −12→12
Absorption correction: analytical [(Oxford Diffraction, 2007); analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995)]	k = −16→16
T_min = 0.883, T_max = 0.904	l = −22→22
54956 measured reflections

Refinement top

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0646P)² + 0.4979P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
4956 reflections	Δρ_max = 0.40 e Å⁻³
314 parameters	Δρ_min = −0.35 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0083 (11)

Crystal data top

C₁₃H₉Cl₂NO	V = 2537.41 (9) Å³
M_r = 266.11	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0431 (2) Å	µ = 0.49 mm⁻¹
b = 13.7150 (3) Å	T = 295 K
c = 18.4585 (4) Å	0.26 × 0.24 × 0.21 mm
β = 93.623 (2)°

Data collection top

Oxford Diffraction Xcalibur System diffractometer	4956 independent reflections
Absorption correction: analytical [(Oxford Diffraction, 2007); analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995)]	3810 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.904	R_int = 0.023
54956 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	2 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.40 e Å⁻³
4956 reflections	Δρ_min = −0.35 e Å⁻³
314 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
C1	0.29163 (15)	0.88930 (13)	0.13557 (10)	0.0468 (4)
C2	0.31340 (17)	0.99515 (13)	0.12131 (10)	0.0496 (4)
C3	0.2344 (2)	1.06295 (18)	0.1520 (2)	0.0957 (10)
H3	0.1718	1.0433	0.184	0.115*
C4	0.2478 (3)	1.1613 (2)	0.1353 (2)	0.1205 (13)
H4	0.1942	1.2072	0.1564	0.145*
C5	0.3392 (3)	1.19053 (19)	0.08819 (19)	0.0957 (10)
H5	0.3447	1.2559	0.0752	0.115*
C6	0.4206 (4)	1.1252 (2)	0.06070 (14)	0.0979 (9)
H6	0.4856	1.1456	0.0304	0.118*
C7	0.4090 (3)	1.02747 (17)	0.07699 (13)	0.0798 (7)
H7	0.4667	0.9828	0.0577	0.096*
C8	0.39430 (16)	0.73180 (13)	0.15565 (12)	0.0555 (5)
C9	0.41165 (19)	0.70599 (15)	0.22837 (14)	0.0661 (6)
C10	0.4153 (2)	0.60990 (18)	0.25095 (17)	0.0805 (7)
H10	0.4284	0.5945	0.3	0.097*
C11	0.3993 (2)	0.53776 (18)	0.19996 (19)	0.0853 (8)
H11	0.4011	0.4729	0.2146	0.102*
C12	0.3805 (2)	0.55993 (17)	0.12743 (18)	0.0822 (8)
H12	0.3702	0.5102	0.0933	0.099*
C13	0.3771 (2)	0.65690 (16)	0.10524 (14)	0.0664 (6)
N1	0.39953 (14)	0.83121 (11)	0.13436 (10)	0.0535 (4)
H1N	0.4772 (19)	0.8565 (16)	0.1310 (11)	0.064*
O1	0.18181 (11)	0.85646 (10)	0.14687 (9)	0.0635 (4)
Cl1	0.42425 (7)	0.79839 (5)	0.29312 (4)	0.0924 (2)
Cl2	0.35242 (9)	0.68484 (5)	0.01367 (4)	0.1030 (3)
C21	0.79317 (15)	0.84885 (12)	0.13788 (10)	0.0457 (4)
C22	0.81608 (17)	0.75379 (13)	0.10084 (11)	0.0505 (4)
C23	0.7373 (2)	0.67477 (16)	0.11555 (17)	0.0803 (8)
H23	0.6724	0.6804	0.1491	0.096*
C24	0.7548 (3)	0.58684 (18)	0.0802 (2)	0.1034 (11)
H24	0.7023	0.5334	0.0906	0.124*
C25	0.8487 (3)	0.57822 (19)	0.03020 (18)	0.0922 (9)
H25	0.8588	0.5193	0.0062	0.111*
C26	0.9277 (3)	0.65546 (18)	0.01526 (13)	0.0761 (7)
H26	0.9919	0.6491	−0.0186	0.091*
C27	0.9124 (2)	0.74372 (15)	0.05076 (11)	0.0588 (5)
H27	0.9669	0.7963	0.0409	0.071*
C28	0.89884 (14)	0.99789 (11)	0.18305 (9)	0.0412 (4)
C29	0.92285 (17)	1.01514 (13)	0.25670 (10)	0.0501 (4)
C30	0.9290 (2)	1.10850 (16)	0.28488 (12)	0.0622 (5)
H30	0.9468	1.1184	0.3344	0.075*
C31	0.9085 (2)	1.18598 (15)	0.23909 (13)	0.0670 (6)
H31	0.9121	1.249	0.2578	0.08*
C32	0.8826 (2)	1.17230 (14)	0.16579 (13)	0.0653 (5)
H32	0.8683	1.2255	0.1351	0.078*
C33	0.87794 (18)	1.07878 (13)	0.13833 (10)	0.0511 (4)
N2	0.90279 (14)	0.90255 (10)	0.15368 (8)	0.0450 (4)
H2N	0.9794 (18)	0.8817 (14)	0.1457 (10)	0.054*
O2	0.68208 (11)	0.87638 (10)	0.15285 (9)	0.0677 (4)
Cl3	0.94534 (8)	0.91674 (5)	0.31518 (3)	0.0865 (2)
Cl4	0.84784 (8)	1.06116 (5)	0.04585 (3)	0.0869 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0336 (8)	0.0493 (10)	0.0569 (10)	−0.0039 (7)	−0.0009 (7)	0.0105 (8)
C2	0.0427 (9)	0.0468 (10)	0.0576 (10)	−0.0041 (8)	−0.0106 (8)	0.0080 (8)
C3	0.0452 (11)	0.0592 (14)	0.185 (3)	0.0027 (10)	0.0251 (15)	0.0048 (16)
C4	0.0598 (15)	0.0540 (15)	0.247 (4)	0.0129 (12)	0.004 (2)	−0.001 (2)
C5	0.0892 (19)	0.0524 (14)	0.139 (3)	−0.0148 (13)	−0.0468 (18)	0.0265 (16)
C6	0.163 (3)	0.0603 (15)	0.0716 (15)	−0.0325 (18)	0.0185 (17)	0.0136 (12)
C7	0.125 (2)	0.0535 (12)	0.0637 (13)	−0.0217 (13)	0.0321 (13)	0.0015 (10)
C8	0.0290 (8)	0.0467 (10)	0.0905 (15)	−0.0013 (7)	0.0021 (8)	0.0144 (10)
C9	0.0424 (10)	0.0583 (12)	0.0961 (16)	−0.0013 (9)	−0.0076 (10)	0.0177 (11)
C10	0.0614 (13)	0.0643 (15)	0.114 (2)	0.0050 (11)	−0.0110 (13)	0.0311 (14)
C11	0.0612 (13)	0.0495 (13)	0.145 (3)	0.0099 (10)	0.0081 (14)	0.0293 (15)
C12	0.0664 (14)	0.0485 (12)	0.133 (2)	−0.0020 (10)	0.0192 (15)	−0.0005 (14)
C13	0.0478 (10)	0.0548 (12)	0.0976 (16)	−0.0053 (9)	0.0116 (10)	0.0053 (11)
N1	0.0312 (7)	0.0452 (8)	0.0843 (11)	−0.0067 (6)	0.0043 (7)	0.0129 (8)
O1	0.0320 (6)	0.0573 (8)	0.1014 (11)	−0.0022 (5)	0.0056 (6)	0.0213 (7)
Cl1	0.1026 (5)	0.0785 (4)	0.0927 (5)	−0.0146 (3)	−0.0221 (4)	0.0098 (3)
Cl2	0.1321 (6)	0.0836 (5)	0.0940 (5)	−0.0293 (4)	0.0131 (4)	−0.0028 (4)
C21	0.0333 (8)	0.0438 (9)	0.0596 (10)	0.0012 (7)	0.0003 (7)	−0.0075 (8)
C22	0.0382 (9)	0.0435 (9)	0.0679 (12)	0.0031 (7)	−0.0111 (8)	−0.0117 (8)
C23	0.0445 (11)	0.0524 (12)	0.145 (2)	−0.0056 (9)	0.0107 (12)	−0.0206 (13)
C24	0.0651 (15)	0.0515 (14)	0.192 (3)	−0.0098 (11)	−0.0021 (18)	−0.0332 (17)
C25	0.0757 (16)	0.0631 (15)	0.134 (2)	0.0173 (13)	−0.0220 (16)	−0.0463 (15)
C26	0.0871 (16)	0.0718 (15)	0.0681 (14)	0.0202 (13)	−0.0060 (12)	−0.0257 (11)
C27	0.0664 (12)	0.0531 (11)	0.0563 (11)	0.0077 (9)	−0.0004 (9)	−0.0102 (9)
C28	0.0288 (7)	0.0404 (9)	0.0547 (10)	−0.0010 (6)	0.0049 (7)	−0.0089 (7)
C29	0.0464 (9)	0.0506 (10)	0.0536 (10)	0.0008 (8)	0.0050 (8)	−0.0060 (8)
C30	0.0624 (12)	0.0631 (13)	0.0613 (12)	−0.0083 (10)	0.0060 (10)	−0.0219 (10)
C31	0.0693 (13)	0.0448 (11)	0.0887 (16)	−0.0085 (9)	0.0194 (11)	−0.0236 (11)
C32	0.0701 (13)	0.0409 (10)	0.0862 (16)	−0.0001 (9)	0.0148 (11)	0.0002 (10)
C33	0.0468 (9)	0.0513 (10)	0.0554 (10)	0.0013 (8)	0.0054 (8)	−0.0051 (8)
N2	0.0290 (6)	0.0427 (8)	0.0634 (9)	0.0026 (6)	0.0029 (6)	−0.0147 (6)
O2	0.0316 (6)	0.0583 (8)	0.1137 (12)	−0.0017 (6)	0.0088 (7)	−0.0256 (8)
Cl3	0.1228 (5)	0.0719 (4)	0.0638 (4)	0.0113 (3)	−0.0019 (3)	0.0093 (3)
Cl4	0.1163 (5)	0.0878 (4)	0.0553 (3)	0.0093 (4)	−0.0057 (3)	0.0019 (3)

Geometric parameters (Å, º) top

C1—O1	1.2214 (19)	C21—O2	1.2258 (19)
C1—N1	1.346 (2)	C21—N2	1.341 (2)
C1—C2	1.494 (2)	C21—C22	1.497 (2)
C2—C3	1.368 (3)	C22—C23	1.379 (3)
C2—C7	1.373 (3)	C22—C27	1.386 (3)
C3—C4	1.391 (4)	C23—C24	1.388 (3)
C3—H3	0.93	C23—H23	0.93
C4—C5	1.364 (5)	C24—C25	1.366 (4)
C4—H4	0.93	C24—H24	0.93
C5—C6	1.335 (4)	C25—C26	1.362 (4)
C5—H5	0.93	C25—H25	0.93
C6—C7	1.380 (3)	C26—C27	1.390 (3)
C6—H6	0.93	C26—H26	0.93
C7—H7	0.93	C27—H27	0.93
C8—C9	1.389 (3)	C28—C29	1.386 (2)
C8—C13	1.389 (3)	C28—C33	1.391 (3)
C8—N1	1.421 (2)	C28—N2	1.417 (2)
C9—C10	1.382 (3)	C29—C30	1.382 (3)
C9—Cl1	1.741 (3)	C29—Cl3	1.734 (2)
C10—C11	1.368 (4)	C30—C31	1.365 (3)
C10—H10	0.93	C30—H30	0.93
C11—C12	1.374 (4)	C31—C32	1.374 (3)
C11—H11	0.93	C31—H31	0.93
C12—C13	1.391 (3)	C32—C33	1.379 (3)
C12—H12	0.93	C32—H32	0.93
C13—Cl2	1.736 (3)	C33—Cl4	1.732 (2)
N1—H1N	0.860 (19)	N2—H2N	0.843 (18)

O1—C1—N1	121.41 (16)	O2—C21—N2	121.88 (16)
O1—C1—C2	122.15 (16)	O2—C21—C22	122.66 (15)
N1—C1—C2	116.43 (14)	N2—C21—C22	115.46 (14)
C3—C2—C7	118.2 (2)	C23—C22—C27	119.09 (18)
C3—C2—C1	119.51 (18)	C23—C22—C21	119.21 (18)
C7—C2—C1	122.29 (18)	C27—C22—C21	121.68 (16)
C2—C3—C4	120.1 (3)	C22—C23—C24	119.9 (2)
C2—C3—H3	120	C22—C23—H23	120
C4—C3—H3	120	C24—C23—H23	120
C5—C4—C3	120.3 (3)	C25—C24—C23	120.4 (2)
C5—C4—H4	119.9	C25—C24—H24	119.8
C3—C4—H4	119.9	C23—C24—H24	119.8
C6—C5—C4	119.9 (2)	C26—C25—C24	120.4 (2)
C6—C5—H5	120.1	C26—C25—H25	119.8
C4—C5—H5	120.1	C24—C25—H25	119.8
C5—C6—C7	120.5 (3)	C25—C26—C27	119.9 (2)
C5—C6—H6	119.8	C25—C26—H26	120.1
C7—C6—H6	119.8	C27—C26—H26	120.1
C2—C7—C6	121.0 (3)	C22—C27—C26	120.3 (2)
C2—C7—H7	119.5	C22—C27—H27	119.9
C6—C7—H7	119.5	C26—C27—H27	119.9
C9—C8—C13	117.49 (18)	C29—C28—C33	117.15 (15)
C9—C8—N1	120.5 (2)	C29—C28—N2	121.70 (16)
C13—C8—N1	122.0 (2)	C33—C28—N2	121.06 (16)
C10—C9—C8	122.3 (2)	C30—C29—C28	121.88 (18)
C10—C9—Cl1	119.2 (2)	C30—C29—Cl3	119.07 (15)
C8—C9—Cl1	118.51 (16)	C28—C29—Cl3	119.05 (13)
C11—C10—C9	118.8 (3)	C31—C30—C29	119.13 (19)
C11—C10—H10	120.6	C31—C30—H30	120.4
C9—C10—H10	120.6	C29—C30—H30	120.4
C10—C11—C12	120.9 (2)	C30—C31—C32	120.99 (18)
C10—C11—H11	119.6	C30—C31—H31	119.5
C12—C11—H11	119.6	C32—C31—H31	119.5
C11—C12—C13	119.8 (3)	C31—C32—C33	119.3 (2)
C11—C12—H12	120.1	C31—C32—H32	120.4
C13—C12—H12	120.1	C33—C32—H32	120.4
C8—C13—C12	120.7 (2)	C32—C33—C28	121.57 (18)
C8—C13—Cl2	119.53 (16)	C32—C33—Cl4	119.47 (16)
C12—C13—Cl2	119.8 (2)	C28—C33—Cl4	118.95 (14)
C1—N1—C8	121.29 (14)	C21—N2—C28	123.19 (14)
C1—N1—H1N	119.9 (14)	C21—N2—H2N	121.5 (13)
C8—N1—H1N	117.2 (15)	C28—N2—H2N	115.3 (13)

O1—C1—C2—C3	30.4 (3)	O2—C21—C22—C23	−34.2 (3)
N1—C1—C2—C3	−150.5 (2)	N2—C21—C22—C23	145.9 (2)
O1—C1—C2—C7	−148.3 (2)	O2—C21—C22—C27	144.2 (2)
N1—C1—C2—C7	30.8 (3)	N2—C21—C22—C27	−35.7 (3)
C7—C2—C3—C4	3.0 (4)	C27—C22—C23—C24	−0.2 (4)
C1—C2—C3—C4	−175.7 (3)	C21—C22—C23—C24	178.3 (2)
C2—C3—C4—C5	0.2 (5)	C22—C23—C24—C25	−0.8 (4)
C3—C4—C5—C6	−3.3 (5)	C23—C24—C25—C26	1.0 (5)
C4—C5—C6—C7	3.0 (5)	C24—C25—C26—C27	−0.4 (4)
C3—C2—C7—C6	−3.3 (4)	C23—C22—C27—C26	0.9 (3)
C1—C2—C7—C6	175.4 (2)	C21—C22—C27—C26	−177.54 (18)
C5—C6—C7—C2	0.4 (4)	C25—C26—C27—C22	−0.6 (3)
C13—C8—C9—C10	1.5 (3)	C33—C28—C29—C30	−1.4 (3)
N1—C8—C9—C10	−176.03 (18)	N2—C28—C29—C30	175.06 (16)
C13—C8—C9—Cl1	−176.52 (14)	C33—C28—C29—Cl3	178.37 (13)
N1—C8—C9—Cl1	5.9 (2)	N2—C28—C29—Cl3	−5.1 (2)
C8—C9—C10—C11	−1.0 (3)	C28—C29—C30—C31	1.2 (3)
Cl1—C9—C10—C11	177.08 (18)	Cl3—C29—C30—C31	−178.63 (16)
C9—C10—C11—C12	0.3 (4)	C29—C30—C31—C32	−0.3 (3)
C10—C11—C12—C13	−0.3 (4)	C30—C31—C32—C33	−0.3 (3)
C9—C8—C13—C12	−1.5 (3)	C31—C32—C33—C28	0.0 (3)
N1—C8—C13—C12	176.04 (18)	C31—C32—C33—Cl4	−179.03 (16)
C9—C8—C13—Cl2	179.02 (14)	C29—C28—C33—C32	0.8 (3)
N1—C8—C13—Cl2	−3.4 (2)	N2—C28—C33—C32	−175.69 (17)
C11—C12—C13—C8	0.9 (3)	C29—C28—C33—Cl4	179.88 (12)
C11—C12—C13—Cl2	−179.60 (17)	N2—C28—C33—Cl4	3.4 (2)
O1—C1—N1—C8	−8.5 (3)	O2—C21—N2—C28	−5.4 (3)
C2—C1—N1—C8	172.35 (18)	C22—C21—N2—C28	174.49 (16)
C9—C8—N1—C1	−84.0 (2)	C29—C28—N2—C21	98.8 (2)
C13—C8—N1—C1	98.5 (2)	C33—C28—N2—C21	−84.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86 (2)	2.09 (2)	2.9035 (18)	158 (2)
N2—H2N···O1ⁱ	0.84 (2)	2.06 (2)	2.8831 (18)	165 (2)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉Cl₂NO
M_r	266.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.0431 (2), 13.7150 (3), 18.4585 (4)
β (°)	93.623 (2)
V (Å³)	2537.41 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.26 × 0.24 × 0.21

Data collection
Diffractometer	Oxford Diffraction Xcalibur System diffractometer
Absorption correction	Analytical [(Oxford Diffraction, 2007); analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995)]
T_min, T_max	0.883, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	54956, 4956, 3810
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.127, 1.10
No. of reflections	4956
No. of parameters	314
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.35

Computer programs: CrysAlis CCD, Oxford Diffraction, 2007, CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.860 (19)	2.09 (2)	2.9035 (18)	158 (2)
N2—H2N···O1ⁱ	0.843 (18)	2.060 (19)	2.8831 (18)	165.1 (19)

Symmetry code: (i) x+1, y, z.

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (Grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

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