N-(2,6-Dichloro-phen-yl)benzamide.

The conformation of the N-H and C=O bonds in the structure of the title compound (N26DCPBA), C(13)H(9)Cl(2)NO, are anti to each other, similar to that observed in N-phenyl-benzamide (NPBA), N-(2-chloro-phen-yl)benzamide (N2CPBA), N-(2,3-dichloro-phen-yl)benzamide (N23DCPBA) and other benzanilides. The asymmetric unit of N26DCPBA contains two mol-ecules. 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 mol-ecule and 35.1 (2)° in the second mol-ecule of the asymmetric unit. The dihedral angle between the two benzene rings (benzoyl and aniline) is 56.8 (1)° in the first mol-ecule and 59.1 (1)° in the second mol-ecule. 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 = 266.11

Monoclinic,

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 ▶); 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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.10

4956 reflections

314 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 ▶).

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

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

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

C13H9Cl2NO	F000 = 1088
Mr = 266.11	Dx = 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 = 3.1–29.5º
b = 13.7150 (3) Å	µ = 0.49 mm−1
c = 18.4585 (4) Å	T = 295 (2) K
β = 93.623 (2)º	Block, colorless
V = 2537.41 (9) Å3	0.26 × 0.24 × 0.21 mm
Z = 8

Oxford Diffraction Xcalibur System diffractometer	4956 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3810 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
Detector resolution: 10.434 pixels mm-1	θmax = 26.0º
T = 295(2) K	θmin = 5.1º
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
Tmin = 0.883, Tmax = 0.904	l = −22→22
54956 measured reflections

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(Fo2) + (0.0646P)2 + 0.4979P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
4956 reflections	Δρmax = 0.40 e Å−3
314 parameters	Δρmin = −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)

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
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)

	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)

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)

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)

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) .