organic compounds
3-Chloro-N-(3-chlorophenyl)benzamide
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com
In the 13H9Cl2NO, the N—H and C=O bonds are anti to each other in the two independent molecules. In one molecule, the N—H bond is syn to the meta-chloro group of the attached ring; it is anti in the other molecule. This relationship is also observed between the C=O bond and the meta-chloro substituent of its attached ring. The amide –NHCO– group makes dihedral angles of 31.5 (4) and 34.7 (3)° with the aniline rings; it makes dihedral angles of 37.4 (3) and 37.2 (3)° with the benzoyl rings. The two rings are nearly coplanar, with dihedral angles of 9.1 (2) and 7.3 (3)° in the two independent molecules. Adjacent molecules are linked into infinite chains through N—H⋯O hydrogen bonds.
of the title compound, CExperimental
Crystal data
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Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell 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, 2003); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536808012099/ng2449sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808012099/ng2449Isup2.hkl
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.
The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å, N—H = 0.86 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).
Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell
CAD-4-PC (Enraf–Nonius, 1996); 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, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C13H9Cl2NO | F(000) = 544 |
Mr = 266.11 | Dx = 1.470 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 8.577 (1) Å | θ = 6.5–27.0° |
b = 13.551 (1) Å | µ = 4.70 mm−1 |
c = 10.357 (1) Å | T = 296 K |
β = 93.04 (1)° | Thick needle, colourless |
V = 1202.1 (2) Å3 | 0.60 × 0.28 × 0.23 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 2165 reflections with I > 2˘I) |
Radiation source: medium-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 67.0°, θmin = 4.3° |
ω–2θ scans | h = −10→3 |
Absorption correction: ψ scan (North et al., 1968) | k = −16→0 |
Tmin = 0.265, Tmax = 0.341 | l = −12→12 |
3088 measured reflections | 3 standard reflections every 120 min |
2249 independent reflections | intensity decay: none |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0835P)2 + 0.4755P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.131 | (Δ/σ)max = 0.010 |
S = 1.10 | Δρmax = 0.37 e Å−3 |
2249 reflections | Δρmin = −0.50 e Å−3 |
308 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0062 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: No Flack (1983), no Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.07 (2) |
C13H9Cl2NO | V = 1202.1 (2) Å3 |
Mr = 266.11 | Z = 4 |
Monoclinic, P21 | Cu Kα radiation |
a = 8.577 (1) Å | µ = 4.70 mm−1 |
b = 13.551 (1) Å | T = 296 K |
c = 10.357 (1) Å | 0.60 × 0.28 × 0.23 mm |
β = 93.04 (1)° |
Enraf–Nonius CAD-4 diffractometer | 2165 reflections with I > 2˘I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.022 |
Tmin = 0.265, Tmax = 0.341 | 3 standard reflections every 120 min |
3088 measured reflections | intensity decay: none |
2249 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.131 | Δρmax = 0.37 e Å−3 |
S = 1.10 | Δρmin = −0.50 e Å−3 |
2249 reflections | Absolute structure: No Flack (1983), no Friedel pairs |
308 parameters | Absolute structure parameter: 0.07 (2) |
1 restraint |
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 | 0.32030 (17) | −0.00289 (12) | −0.13075 (14) | 0.0740 (5) | |
Cl2 | 1.14912 (18) | 0.14458 (13) | 0.63527 (15) | 0.0799 (5) | |
O1 | 0.5608 (3) | 0.1667 (2) | 0.2587 (3) | 0.0503 (8) | |
N1 | 0.7425 (4) | 0.0481 (3) | 0.2308 (4) | 0.0460 (8) | |
H1N | 0.8369 | 0.0308 | 0.2520 | 0.055* | |
C1 | 0.6552 (5) | −0.0173 (3) | 0.1482 (4) | 0.0431 (10) | |
C2 | 0.5418 (5) | 0.0182 (4) | 0.0581 (4) | 0.0456 (10) | |
H2 | 0.5206 | 0.0853 | 0.0511 | 0.055* | |
C3 | 0.4622 (5) | −0.0494 (4) | −0.0200 (4) | 0.0445 (10) | |
C4 | 0.4926 (6) | −0.1489 (4) | −0.0152 (5) | 0.0515 (11) | |
H4 | 0.4385 | −0.1926 | −0.0703 | 0.062* | |
C5 | 0.6063 (6) | −0.1817 (4) | 0.0742 (4) | 0.0535 (11) | |
H5 | 0.6279 | −0.2489 | 0.0807 | 0.064* | |
C6 | 0.6879 (5) | −0.1163 (4) | 0.1537 (4) | 0.0488 (10) | |
H6 | 0.7660 | −0.1394 | 0.2117 | 0.059* | |
C7 | 0.6948 (4) | 0.1331 (3) | 0.2792 (4) | 0.0422 (9) | |
C8 | 0.8119 (4) | 0.1892 (4) | 0.3622 (4) | 0.0393 (9) | |
C9 | 0.9189 (5) | 0.1425 (4) | 0.4483 (4) | 0.0441 (9) | |
H9 | 0.9228 | 0.0741 | 0.4541 | 0.053* | |
C10 | 1.0191 (5) | 0.2006 (4) | 0.5251 (4) | 0.0459 (10) | |
C11 | 1.0193 (6) | 0.3013 (4) | 0.5145 (5) | 0.0485 (10) | |
H11 | 1.0898 | 0.3389 | 0.5649 | 0.058* | |
C12 | 0.9142 (5) | 0.3464 (4) | 0.4286 (5) | 0.0496 (11) | |
H12 | 0.9139 | 0.4148 | 0.4208 | 0.060* | |
C13 | 0.8099 (5) | 0.2910 (4) | 0.3546 (4) | 0.0456 (10) | |
H13 | 0.7371 | 0.3222 | 0.2987 | 0.055* | |
Cl3 | 0.1457 (2) | 0.46405 (11) | 0.18206 (16) | 0.0753 (4) | |
Cl4 | 0.39972 (18) | −0.34554 (10) | 0.31885 (16) | 0.0731 (4) | |
O2 | 0.0590 (3) | −0.0229 (2) | 0.2416 (3) | 0.0517 (8) | |
N2 | 0.2432 (4) | 0.0962 (3) | 0.2377 (4) | 0.0485 (9) | |
H2N | 0.3378 | 0.1108 | 0.2621 | 0.058* | |
C14 | 0.1548 (5) | 0.1709 (3) | 0.1702 (4) | 0.0428 (10) | |
C15 | 0.1861 (5) | 0.2671 (4) | 0.2042 (4) | 0.0465 (10) | |
H15 | 0.2607 | 0.2819 | 0.2697 | 0.056* | |
C16 | 0.1049 (6) | 0.3412 (4) | 0.1395 (5) | 0.0502 (11) | |
C17 | −0.0064 (6) | 0.3217 (4) | 0.0413 (5) | 0.0576 (12) | |
H17 | −0.0604 | 0.3727 | −0.0011 | 0.069* | |
C18 | −0.0353 (6) | 0.2251 (4) | 0.0079 (5) | 0.0604 (13) | |
H18 | −0.1089 | 0.2106 | −0.0585 | 0.072* | |
C19 | 0.0435 (6) | 0.1493 (4) | 0.0719 (4) | 0.0532 (10) | |
H19 | 0.0222 | 0.0841 | 0.0493 | 0.064* | |
C20 | 0.1947 (5) | 0.0069 (3) | 0.2667 (4) | 0.0433 (9) | |
C21 | 0.3143 (5) | −0.0594 (3) | 0.3333 (4) | 0.0425 (9) | |
C22 | 0.3057 (5) | −0.1578 (4) | 0.3017 (4) | 0.0425 (10) | |
H22 | 0.2313 | −0.1802 | 0.2400 | 0.051* | |
C23 | 0.4090 (5) | −0.2227 (3) | 0.3627 (4) | 0.0464 (10) | |
C24 | 0.5166 (5) | −0.1926 (4) | 0.4561 (5) | 0.0518 (11) | |
H24 | 0.5846 | −0.2378 | 0.4966 | 0.062* | |
C25 | 0.5229 (6) | −0.0953 (4) | 0.4891 (5) | 0.0560 (12) | |
H25 | 0.5951 | −0.0742 | 0.5535 | 0.067* | |
C26 | 0.4227 (5) | −0.0268 (4) | 0.4277 (4) | 0.0477 (10) | |
H26 | 0.4286 | 0.0397 | 0.4498 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0702 (8) | 0.0747 (9) | 0.0728 (8) | −0.0055 (7) | −0.0370 (6) | 0.0012 (7) |
Cl2 | 0.0704 (8) | 0.0792 (10) | 0.0852 (10) | −0.0037 (8) | −0.0431 (7) | 0.0120 (8) |
O1 | 0.0270 (13) | 0.052 (2) | 0.0705 (19) | 0.0027 (12) | −0.0092 (12) | −0.0101 (15) |
N1 | 0.0294 (16) | 0.051 (2) | 0.056 (2) | 0.0007 (15) | −0.0091 (14) | −0.0052 (18) |
C1 | 0.0343 (19) | 0.048 (3) | 0.046 (2) | −0.0029 (18) | 0.0001 (16) | −0.0051 (19) |
C2 | 0.042 (2) | 0.045 (2) | 0.049 (2) | −0.0022 (18) | −0.0042 (17) | −0.0010 (19) |
C3 | 0.034 (2) | 0.056 (3) | 0.042 (2) | −0.0049 (19) | −0.0059 (17) | −0.004 (2) |
C4 | 0.047 (2) | 0.059 (3) | 0.048 (2) | −0.011 (2) | −0.0056 (19) | −0.009 (2) |
C5 | 0.060 (3) | 0.046 (3) | 0.055 (3) | 0.003 (2) | 0.003 (2) | −0.006 (2) |
C6 | 0.042 (2) | 0.061 (3) | 0.042 (2) | 0.000 (2) | −0.0042 (17) | −0.001 (2) |
C7 | 0.0293 (18) | 0.050 (3) | 0.047 (2) | −0.0013 (18) | −0.0030 (15) | 0.0009 (19) |
C8 | 0.0307 (18) | 0.048 (2) | 0.0391 (19) | −0.0065 (17) | −0.0021 (15) | −0.0006 (17) |
C9 | 0.041 (2) | 0.042 (2) | 0.048 (2) | −0.0057 (19) | −0.0043 (17) | 0.0012 (19) |
C10 | 0.037 (2) | 0.057 (3) | 0.043 (2) | 0.0004 (19) | −0.0072 (16) | 0.002 (2) |
C11 | 0.047 (2) | 0.052 (3) | 0.047 (2) | −0.010 (2) | −0.0028 (18) | −0.011 (2) |
C12 | 0.049 (3) | 0.041 (2) | 0.058 (3) | −0.0035 (19) | 0.003 (2) | −0.006 (2) |
C13 | 0.039 (2) | 0.049 (3) | 0.049 (2) | 0.0023 (18) | 0.0013 (17) | 0.002 (2) |
Cl3 | 0.0863 (10) | 0.0465 (7) | 0.0935 (10) | 0.0010 (7) | 0.0074 (8) | 0.0058 (7) |
Cl4 | 0.0804 (8) | 0.0452 (7) | 0.0932 (10) | 0.0119 (6) | 0.0009 (7) | −0.0068 (7) |
O2 | 0.0252 (13) | 0.0485 (18) | 0.080 (2) | −0.0024 (13) | −0.0067 (12) | 0.0044 (16) |
N2 | 0.0358 (19) | 0.047 (2) | 0.062 (2) | 0.0023 (16) | −0.0041 (16) | 0.0028 (19) |
C14 | 0.0340 (19) | 0.049 (3) | 0.046 (2) | 0.0101 (17) | 0.0044 (16) | 0.0074 (19) |
C15 | 0.040 (2) | 0.049 (3) | 0.051 (2) | 0.0023 (19) | 0.0038 (18) | 0.0041 (19) |
C16 | 0.049 (2) | 0.044 (3) | 0.059 (3) | 0.0066 (19) | 0.009 (2) | 0.005 (2) |
C17 | 0.051 (3) | 0.062 (3) | 0.059 (3) | 0.015 (2) | −0.004 (2) | 0.015 (2) |
C18 | 0.053 (3) | 0.066 (3) | 0.060 (3) | 0.007 (2) | −0.015 (2) | 0.008 (3) |
C19 | 0.060 (3) | 0.049 (2) | 0.049 (2) | 0.004 (2) | −0.0058 (19) | 0.002 (2) |
C20 | 0.038 (2) | 0.044 (2) | 0.048 (2) | 0.0064 (18) | −0.0026 (16) | −0.0033 (19) |
C21 | 0.039 (2) | 0.045 (2) | 0.043 (2) | 0.0084 (18) | 0.0011 (16) | 0.0008 (18) |
C22 | 0.0335 (19) | 0.052 (3) | 0.041 (2) | 0.0070 (18) | −0.0013 (16) | −0.0019 (18) |
C23 | 0.046 (2) | 0.042 (2) | 0.051 (2) | 0.0043 (19) | 0.0058 (18) | 0.0039 (19) |
C24 | 0.044 (2) | 0.051 (3) | 0.060 (3) | 0.012 (2) | −0.005 (2) | 0.012 (2) |
C25 | 0.047 (3) | 0.066 (3) | 0.054 (2) | −0.004 (2) | −0.013 (2) | 0.004 (2) |
C26 | 0.050 (2) | 0.040 (2) | 0.052 (2) | 0.002 (2) | −0.0029 (18) | 0.000 (2) |
Cl1—C3 | 1.745 (4) | Cl3—C16 | 1.753 (5) |
Cl2—C10 | 1.729 (4) | Cl4—C23 | 1.726 (5) |
O1—C7 | 1.244 (5) | O2—C20 | 1.246 (5) |
N1—C7 | 1.330 (6) | N2—C20 | 1.319 (6) |
N1—C1 | 1.418 (5) | N2—C14 | 1.425 (5) |
N1—H1N | 0.8600 | N2—H2N | 0.8600 |
C1—C6 | 1.370 (7) | C14—C15 | 1.373 (7) |
C1—C2 | 1.397 (6) | C14—C19 | 1.390 (6) |
C2—C3 | 1.379 (6) | C15—C16 | 1.376 (7) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.373 (7) | C16—C17 | 1.383 (7) |
C4—C5 | 1.383 (7) | C17—C18 | 1.373 (8) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C5—C6 | 1.376 (7) | C18—C19 | 1.380 (7) |
C5—H5 | 0.9300 | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C7—C8 | 1.493 (6) | C20—C21 | 1.503 (6) |
C8—C13 | 1.382 (6) | C21—C22 | 1.374 (6) |
C8—C9 | 1.397 (6) | C21—C26 | 1.386 (6) |
C9—C10 | 1.385 (6) | C22—C23 | 1.378 (6) |
C9—H9 | 0.9300 | C22—H22 | 0.9300 |
C10—C11 | 1.369 (7) | C23—C24 | 1.363 (7) |
C11—C12 | 1.375 (7) | C24—C25 | 1.364 (8) |
C11—H11 | 0.9300 | C24—H24 | 0.9300 |
C12—C13 | 1.372 (6) | C25—C26 | 1.395 (7) |
C12—H12 | 0.9300 | C25—H25 | 0.9300 |
C13—H13 | 0.9300 | C26—H26 | 0.9300 |
C7—N1—C1 | 127.3 (4) | C20—N2—C14 | 126.6 (4) |
C7—N1—H1N | 116.3 | C20—N2—H2N | 116.7 |
C1—N1—H1N | 116.3 | C14—N2—H2N | 116.7 |
C6—C1—C2 | 119.9 (4) | C15—C14—C19 | 120.3 (4) |
C6—C1—N1 | 119.1 (4) | C15—C14—N2 | 117.2 (4) |
C2—C1—N1 | 121.0 (4) | C19—C14—N2 | 122.5 (4) |
C3—C2—C1 | 117.9 (4) | C14—C15—C16 | 118.8 (4) |
C3—C2—H2 | 121.0 | C14—C15—H15 | 120.6 |
C1—C2—H2 | 121.0 | C16—C15—H15 | 120.6 |
C4—C3—C2 | 122.9 (5) | C15—C16—C17 | 122.0 (5) |
C4—C3—Cl1 | 120.2 (4) | C15—C16—Cl3 | 118.8 (4) |
C2—C3—Cl1 | 116.9 (4) | C17—C16—Cl3 | 119.2 (4) |
C3—C4—C5 | 117.8 (4) | C18—C17—C16 | 118.4 (5) |
C3—C4—H4 | 121.1 | C18—C17—H17 | 120.8 |
C5—C4—H4 | 121.1 | C16—C17—H17 | 120.8 |
C6—C5—C4 | 120.7 (5) | C17—C18—C19 | 120.8 (5) |
C6—C5—H5 | 119.6 | C17—C18—H18 | 119.6 |
C4—C5—H5 | 119.6 | C19—C18—H18 | 119.6 |
C1—C6—C5 | 120.6 (4) | C18—C19—C14 | 119.7 (5) |
C1—C6—H6 | 119.7 | C18—C19—H19 | 120.2 |
C5—C6—H6 | 119.7 | C14—C19—H19 | 120.2 |
O1—C7—N1 | 123.5 (4) | O2—C20—N2 | 123.5 (4) |
O1—C7—C8 | 120.0 (4) | O2—C20—C21 | 120.6 (4) |
N1—C7—C8 | 116.5 (4) | N2—C20—C21 | 115.9 (4) |
C13—C8—C9 | 119.6 (4) | C22—C21—C26 | 120.2 (4) |
C13—C8—C7 | 118.0 (4) | C22—C21—C20 | 116.3 (4) |
C9—C8—C7 | 122.4 (4) | C26—C21—C20 | 123.3 (4) |
C10—C9—C8 | 118.4 (4) | C21—C22—C23 | 119.0 (4) |
C10—C9—H9 | 120.8 | C21—C22—H22 | 120.5 |
C8—C9—H9 | 120.8 | C23—C22—H22 | 120.5 |
C11—C10—C9 | 121.6 (4) | C24—C23—C22 | 121.9 (5) |
C11—C10—Cl2 | 119.2 (4) | C24—C23—Cl4 | 119.7 (4) |
C9—C10—Cl2 | 119.2 (4) | C22—C23—Cl4 | 118.4 (4) |
C10—C11—C12 | 119.4 (5) | C25—C24—C23 | 118.9 (4) |
C10—C11—H11 | 120.3 | C25—C24—H24 | 120.5 |
C12—C11—H11 | 120.3 | C23—C24—H24 | 120.5 |
C13—C12—C11 | 120.3 (5) | C24—C25—C26 | 120.9 (5) |
C13—C12—H12 | 119.9 | C24—C25—H25 | 119.5 |
C11—C12—H12 | 119.9 | C26—C25—H25 | 119.5 |
C12—C13—C8 | 120.6 (4) | C21—C26—C25 | 118.9 (5) |
C12—C13—H13 | 119.7 | C21—C26—H26 | 120.5 |
C8—C13—H13 | 119.7 | C25—C26—H26 | 120.5 |
C7—N1—C1—C6 | −150.4 (5) | C20—N2—C14—C15 | 147.2 (5) |
C7—N1—C1—C2 | 32.5 (7) | C20—N2—C14—C19 | −34.2 (7) |
C6—C1—C2—C3 | 2.2 (6) | C19—C14—C15—C16 | 0.3 (6) |
N1—C1—C2—C3 | 179.4 (4) | N2—C14—C15—C16 | 178.9 (4) |
C1—C2—C3—C4 | −1.8 (7) | C14—C15—C16—C17 | −0.3 (7) |
C1—C2—C3—Cl1 | 179.6 (3) | C14—C15—C16—Cl3 | −179.6 (3) |
C2—C3—C4—C5 | 1.3 (7) | C15—C16—C17—C18 | −0.3 (8) |
Cl1—C3—C4—C5 | 179.9 (4) | Cl3—C16—C17—C18 | 179.1 (4) |
C3—C4—C5—C6 | −1.2 (7) | C16—C17—C18—C19 | 0.8 (8) |
C2—C1—C6—C5 | −2.3 (7) | C17—C18—C19—C14 | −0.8 (8) |
N1—C1—C6—C5 | −179.5 (4) | C15—C14—C19—C18 | 0.2 (7) |
C4—C5—C6—C1 | 1.7 (7) | N2—C14—C19—C18 | −178.3 (4) |
C1—N1—C7—O1 | 1.2 (7) | C14—N2—C20—O2 | −2.7 (7) |
C1—N1—C7—C8 | −178.8 (4) | C14—N2—C20—C21 | 177.2 (4) |
O1—C7—C8—C13 | −36.2 (6) | O2—C20—C21—C22 | 35.5 (6) |
N1—C7—C8—C13 | 143.8 (4) | N2—C20—C21—C22 | −144.4 (4) |
O1—C7—C8—C9 | 142.1 (4) | O2—C20—C21—C26 | −140.5 (4) |
N1—C7—C8—C9 | −37.9 (6) | N2—C20—C21—C26 | 39.5 (6) |
C13—C8—C9—C10 | 0.8 (6) | C26—C21—C22—C23 | −1.7 (6) |
C7—C8—C9—C10 | −177.5 (4) | C20—C21—C22—C23 | −177.9 (4) |
C8—C9—C10—C11 | −2.6 (7) | C21—C22—C23—C24 | 1.9 (7) |
C8—C9—C10—Cl2 | 178.4 (3) | C21—C22—C23—Cl4 | −178.4 (3) |
C9—C10—C11—C12 | 2.1 (8) | C22—C23—C24—C25 | −0.6 (7) |
Cl2—C10—C11—C12 | −178.8 (4) | Cl4—C23—C24—C25 | 179.7 (4) |
C10—C11—C12—C13 | 0.2 (7) | C23—C24—C25—C26 | −0.8 (8) |
C11—C12—C13—C8 | −2.0 (7) | C22—C21—C26—C25 | 0.3 (6) |
C9—C8—C13—C12 | 1.5 (7) | C20—C21—C26—C25 | 176.3 (4) |
C7—C8—C13—C12 | 179.8 (4) | C24—C25—C26—C21 | 0.9 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O2i | 0.86 | 2.05 | 2.877 (4) | 162 |
N2—H2n···O1 | 0.86 | 2.06 | 2.884 (5) | 161 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C13H9Cl2NO |
Mr | 266.11 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 8.577 (1), 13.551 (1), 10.357 (1) |
β (°) | 93.04 (1) |
V (Å3) | 1202.1 (2) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 4.70 |
Crystal size (mm) | 0.60 × 0.28 × 0.23 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.265, 0.341 |
No. of measured, independent and observed [I > 2˘I)] reflections | 3088, 2249, 2165 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.131, 1.10 |
No. of reflections | 2249 |
No. of parameters | 308 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.50 |
Absolute structure | No Flack (1983), no Friedel pairs |
Absolute structure parameter | 0.07 (2) |
Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···O2i | 0.86 | 2.05 | 2.877 (4) | 161.7 |
N2—H2n···O1 | 0.86 | 2.06 | 2.884 (5) | 160.5 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.
References
Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2007). Acta Cryst. E63, o3789. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o462. Web of Science CSD CrossRef IUCr Journals Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
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As part of a study of the substituent effects on the structures of N-aromatic amides,in the present work, the structure of 3-Chloro-N-(3-chlorophenyl)- benzamide(N3CP3CBA) has been determined(Gowda et al., 2003; 2007, 2008). In the structure of N3CP3CBA (Fig. 1),the conformations of the N—H and C=O bonds are anti to each other. The asymmetric unit of the structure contains two molecules. In one of the molecules, the conformation of the N—H bond is syn to the meta-chloro group in the aniline ring and anti to each other in the other molecule. Similar conformations were observed between the C=O bond and meta-chloro substituent in the benzoyl ring. This is in contrast to the single molecule observed in the asymmetric unit of 2-chloro-N-(2-Chlorophenyl)-benzamide (N2CP2CBA) and syn conformation of the N—H bond to the ortho-chloro substituent in the aniline ring and the C=O bond to the ortho-chloro substituent in the benzoyl ring (Gowda et al., 2007). The bond parameters in N3CP3CBA are similar to those in N-(3-chlorophenyl)-benzamide, N2CP2CBA and other benzanilides (Gowda et al., 2003; 2008). The amide group,-NHCO– makes the dihedral angles of 31.5 (4), 37.4 (3)° (molecule 1) and 34.7 (3), 37.2 (3)° (molecule 2) with the aniline and benzoyl rings, respectively, while those between the benzoyl and aniline rings are 9.1 (2)° and 7.3 (3)° in the molecules 1 and 2, respectively. The packing diagram of N3CP3CBA molecules showing the hydrogen bonds N1—H1N···O2 and N2—H2N···O1 (Table 1) involved in the formation of molecular chains is given in Fig. 2.