

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030243/bt2404sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030243/bt2404Isup2.hkl |
CCDC reference: 655047
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.
H atoms were found in a difference map and refined using a riding model with C—H distances of 0.93 Å and 0.86 Å for the H—N distance and with Uiso(H) = 1.2 Ueq(C,N).
In the present work, the structure of N-(2,3-dichlorophenyl)-benzamide has been determined to explore the substituent effects on the structures of N-aromatic amides (Gowda et al., 2003; Gowda, Foro, & Fuess, 2007; Gowda, Kozisek, et al., 2007; Gowda, Sowmya, et al., 2007). The conformation of the N—H bond (Fig. 1) is syn to the chloro substituents in the aniline phenyl ring, similar to that observed in N-(2,3-dichlorophenyl)-acetamide (Gowda, Foro, & Fuess, 2007), but in contrast to the anti conformation observed with respect to the ortho-Cl substituent in N-(2-chlorophenyl)-benzamide (Gowda, Sowmya, et al., 2007). The structure resembles the structure of N-(phenyl)-2-chlorobenzamide (Gowda et al., 2003), N-(2-chlorophenyl)-benzamide (Gowda, Sowmya, et al., 2007) and N-(2,3-dichlorophenyl)-acetamide (Gowda, Foro, & Fuess, 2007). The packing diagram showis the infinite chain of molecules along [0 0 1] linked by N—H···O hydrogen bonds (Fig. 2 and Table 2).
For related literature, see: Gowda et al. (2003); Gowda, Foro & Fuess (2007); Gowda, Kozisek et al. (2007); Gowda, Sowmya et al. (2007).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); 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).
C13H9Cl2NO | F(000) = 1088 |
Mr = 266.11 | Dx = 1.47 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 2616 reflections |
a = 24.2968 (12) Å | θ = 3.1–29.4° |
b = 11.3273 (5) Å | µ = 0.52 mm−1 |
c = 8.7396 (3) Å | T = 295 K |
V = 2405.29 (18) Å3 | Needle, colorless |
Z = 8 | 0.45 × 0.09 × 0.07 mm |
Oxford Diffraction Xcalibur diffractometer | 2319 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 981 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
Detector resolution: 10.4340 pixels mm-1 | θmax = 25.9°, θmin = 4.3° |
φ scans, and ω scans with κ offsets | h = −29→29 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −13→13 |
Tmin = 0.894, Tmax = 0.961 | l = −10→10 |
21027 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0374P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.093 | (Δ/σ)max = 0.002 |
S = 0.91 | Δρmax = 0.17 e Å−3 |
2319 reflections | Δρmin = −0.19 e Å−3 |
154 parameters |
C13H9Cl2NO | V = 2405.29 (18) Å3 |
Mr = 266.11 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 24.2968 (12) Å | µ = 0.52 mm−1 |
b = 11.3273 (5) Å | T = 295 K |
c = 8.7396 (3) Å | 0.45 × 0.09 × 0.07 mm |
Oxford Diffraction Xcalibur diffractometer | 2319 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 981 reflections with I > 2σ(I) |
Tmin = 0.894, Tmax = 0.961 | Rint = 0.097 |
21027 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.17 e Å−3 |
2319 reflections | Δρmin = −0.19 e Å−3 |
154 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.37448 (11) | 0.4513 (3) | 0.2398 (3) | 0.0476 (7) | |
C2 | 0.33837 (11) | 0.3829 (3) | 0.3452 (3) | 0.0444 (7) | |
C3 | 0.34131 (12) | 0.2616 (3) | 0.3412 (3) | 0.0555 (8) | |
H3 | 0.3652 | 0.2249 | 0.2730 | 0.067* | |
C4 | 0.30922 (14) | 0.1938 (3) | 0.4369 (4) | 0.0676 (9) | |
H4 | 0.3122 | 0.1120 | 0.4358 | 0.081* | |
C5 | 0.27301 (13) | 0.2478 (4) | 0.5336 (4) | 0.0709 (10) | |
H5 | 0.2513 | 0.2023 | 0.5986 | 0.085* | |
C6 | 0.26823 (13) | 0.3682 (4) | 0.5359 (4) | 0.0712 (10) | |
H6 | 0.2429 | 0.4040 | 0.6009 | 0.085* | |
C7 | 0.30086 (12) | 0.4365 (3) | 0.4420 (3) | 0.0562 (8) | |
H7 | 0.2977 | 0.5183 | 0.4437 | 0.067* | |
C8 | 0.41571 (11) | 0.6480 (3) | 0.1992 (3) | 0.0422 (7) | |
C9 | 0.45461 (12) | 0.6195 (3) | 0.0898 (3) | 0.0559 (8) | |
H9 | 0.4629 | 0.5408 | 0.0700 | 0.067* | |
C10 | 0.48119 (12) | 0.7080 (3) | 0.0099 (3) | 0.0632 (9) | |
H10 | 0.5071 | 0.6881 | −0.0641 | 0.076* | |
C11 | 0.47010 (12) | 0.8235 (3) | 0.0375 (4) | 0.0646 (9) | |
H11 | 0.4883 | 0.8820 | −0.0174 | 0.078* | |
C12 | 0.43170 (13) | 0.8539 (3) | 0.1474 (3) | 0.0560 (8) | |
C13 | 0.40443 (11) | 0.7666 (3) | 0.2283 (3) | 0.0477 (8) | |
N1 | 0.38766 (9) | 0.5620 (2) | 0.2842 (2) | 0.0491 (6) | |
H1N | 0.3777 | 0.5821 | 0.3750 | 0.059* | |
O1 | 0.39099 (8) | 0.40812 (18) | 0.1197 (2) | 0.0641 (6) | |
Cl1 | 0.35585 (4) | 0.80396 (7) | 0.36269 (8) | 0.0689 (3) | |
Cl2 | 0.41772 (4) | 1.00012 (8) | 0.18131 (11) | 0.0968 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0566 (19) | 0.043 (2) | 0.0428 (17) | 0.0072 (16) | −0.0068 (15) | −0.0002 (16) |
C2 | 0.0485 (19) | 0.045 (2) | 0.0400 (15) | −0.0013 (15) | −0.0039 (14) | −0.0011 (16) |
C3 | 0.060 (2) | 0.055 (2) | 0.0521 (17) | 0.0006 (16) | −0.0035 (17) | −0.0026 (17) |
C4 | 0.071 (2) | 0.054 (2) | 0.077 (2) | −0.014 (2) | −0.012 (2) | 0.012 (2) |
C5 | 0.056 (2) | 0.090 (3) | 0.066 (2) | −0.022 (2) | −0.0032 (19) | 0.018 (2) |
C6 | 0.058 (2) | 0.083 (3) | 0.072 (2) | −0.011 (2) | 0.0035 (18) | −0.004 (2) |
C7 | 0.057 (2) | 0.054 (2) | 0.0570 (18) | −0.0028 (18) | −0.0022 (17) | −0.0011 (18) |
C8 | 0.0471 (18) | 0.044 (2) | 0.0357 (15) | 0.0009 (15) | −0.0022 (13) | 0.0061 (14) |
C9 | 0.0564 (19) | 0.059 (2) | 0.0526 (17) | 0.0070 (17) | 0.0064 (16) | 0.0028 (17) |
C10 | 0.050 (2) | 0.077 (3) | 0.0624 (19) | 0.0063 (19) | 0.0122 (16) | 0.003 (2) |
C11 | 0.055 (2) | 0.063 (3) | 0.075 (2) | −0.0085 (19) | 0.0081 (18) | 0.0079 (19) |
C12 | 0.060 (2) | 0.051 (2) | 0.0569 (18) | −0.0016 (16) | −0.0002 (17) | 0.0035 (17) |
C13 | 0.0522 (19) | 0.051 (2) | 0.0402 (15) | −0.0011 (16) | −0.0025 (14) | 0.0012 (15) |
N1 | 0.0679 (16) | 0.0411 (16) | 0.0383 (12) | 0.0027 (14) | 0.0059 (11) | −0.0020 (13) |
O1 | 0.0942 (16) | 0.0539 (14) | 0.0442 (11) | 0.0014 (12) | 0.0097 (11) | −0.0086 (10) |
Cl1 | 0.0925 (6) | 0.0530 (5) | 0.0613 (5) | 0.0056 (5) | 0.0242 (4) | −0.0040 (4) |
Cl2 | 0.1238 (8) | 0.0477 (6) | 0.1188 (8) | −0.0073 (5) | 0.0328 (6) | 0.0059 (5) |
C1—O1 | 1.226 (3) | C8—C9 | 1.383 (4) |
C1—N1 | 1.351 (3) | C8—C13 | 1.395 (4) |
C1—C2 | 1.490 (4) | C8—N1 | 1.401 (3) |
C2—C3 | 1.377 (4) | C9—C10 | 1.382 (4) |
C2—C7 | 1.384 (4) | C9—H9 | 0.9300 |
C3—C4 | 1.377 (4) | C10—C11 | 1.357 (4) |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
C4—C5 | 1.364 (4) | C11—C12 | 1.383 (4) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—C6 | 1.369 (5) | C12—C13 | 1.384 (4) |
C5—H5 | 0.9300 | C12—Cl2 | 1.716 (3) |
C6—C7 | 1.378 (4) | C13—Cl1 | 1.718 (3) |
C6—H6 | 0.9300 | N1—H1N | 0.8600 |
C7—H7 | 0.9300 | ||
O1—C1—N1 | 122.6 (3) | C9—C8—C13 | 119.0 (3) |
O1—C1—C2 | 120.9 (3) | C9—C8—N1 | 122.5 (3) |
N1—C1—C2 | 116.4 (2) | C13—C8—N1 | 118.5 (2) |
C3—C2—C7 | 119.2 (3) | C10—C9—C8 | 120.0 (3) |
C3—C2—C1 | 118.3 (3) | C10—C9—H9 | 120.0 |
C7—C2—C1 | 122.5 (3) | C8—C9—H9 | 120.0 |
C2—C3—C4 | 120.7 (3) | C11—C10—C9 | 121.1 (3) |
C2—C3—H3 | 119.6 | C11—C10—H10 | 119.4 |
C4—C3—H3 | 119.6 | C9—C10—H10 | 119.4 |
C5—C4—C3 | 119.4 (3) | C10—C11—C12 | 119.9 (3) |
C5—C4—H4 | 120.3 | C10—C11—H11 | 120.1 |
C3—C4—H4 | 120.3 | C12—C11—H11 | 120.1 |
C4—C5—C6 | 120.7 (3) | C11—C12—C13 | 119.9 (3) |
C4—C5—H5 | 119.7 | C11—C12—Cl2 | 119.6 (3) |
C6—C5—H5 | 119.7 | C13—C12—Cl2 | 120.4 (2) |
C5—C6—C7 | 120.1 (3) | C12—C13—C8 | 120.1 (2) |
C5—C6—H6 | 120.0 | C12—C13—Cl1 | 120.1 (2) |
C7—C6—H6 | 120.0 | C8—C13—Cl1 | 119.8 (2) |
C6—C7—C2 | 119.8 (3) | C1—N1—C8 | 127.4 (2) |
C6—C7—H7 | 120.1 | C1—N1—H1N | 116.3 |
C2—C7—H7 | 120.1 | C8—N1—H1N | 116.3 |
O1—C1—C2—C3 | 25.7 (4) | C9—C10—C11—C12 | 0.1 (5) |
N1—C1—C2—C3 | −154.3 (2) | C10—C11—C12—C13 | −0.4 (4) |
O1—C1—C2—C7 | −151.9 (3) | C10—C11—C12—Cl2 | −179.8 (2) |
N1—C1—C2—C7 | 28.1 (4) | C11—C12—C13—C8 | 0.1 (4) |
C7—C2—C3—C4 | −2.9 (4) | Cl2—C12—C13—C8 | 179.5 (2) |
C1—C2—C3—C4 | 179.4 (2) | C11—C12—C13—Cl1 | −178.9 (2) |
C2—C3—C4—C5 | 1.9 (4) | Cl2—C12—C13—Cl1 | 0.5 (3) |
C3—C4—C5—C6 | 0.2 (5) | C9—C8—C13—C12 | 0.4 (4) |
C4—C5—C6—C7 | −1.2 (5) | N1—C8—C13—C12 | 179.5 (2) |
C5—C6—C7—C2 | 0.1 (4) | C9—C8—C13—Cl1 | 179.48 (19) |
C3—C2—C7—C6 | 1.9 (4) | N1—C8—C13—Cl1 | −1.5 (3) |
C1—C2—C7—C6 | 179.4 (3) | O1—C1—N1—C8 | 7.4 (4) |
C13—C8—C9—C10 | −0.7 (4) | C2—C1—N1—C8 | −172.6 (2) |
N1—C8—C9—C10 | −179.7 (3) | C9—C8—N1—C1 | −30.1 (4) |
C8—C9—C10—C11 | 0.5 (4) | C13—C8—N1—C1 | 150.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 2.17 | 2.952 (3) | 152 |
N1—H1N···Cl1 | 0.86 | 2.57 | 2.929 (3) | 106 |
C9—H9···O1 | 0.93 | 2.34 | 2.861 (4) | 115 |
Symmetry code: (i) x, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H9Cl2NO |
Mr | 266.11 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 295 |
a, b, c (Å) | 24.2968 (12), 11.3273 (5), 8.7396 (3) |
V (Å3) | 2405.29 (18) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.52 |
Crystal size (mm) | 0.45 × 0.09 × 0.07 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.894, 0.961 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21027, 2319, 981 |
Rint | 0.097 |
(sin θ/λ)max (Å−1) | 0.613 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.093, 0.91 |
No. of reflections | 2319 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.19 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 2.17 | 2.952 (3) | 151.9 |
N1—H1N···Cl1 | 0.86 | 2.57 | 2.929 (3) | 106.1 |
C9—H9···O1 | 0.93 | 2.34 | 2.861 (4) | 114.8 |
Symmetry code: (i) x, −y+1, z+1/2. |
In the present work, the structure of N-(2,3-dichlorophenyl)-benzamide has been determined to explore the substituent effects on the structures of N-aromatic amides (Gowda et al., 2003; Gowda, Foro, & Fuess, 2007; Gowda, Kozisek, et al., 2007; Gowda, Sowmya, et al., 2007). The conformation of the N—H bond (Fig. 1) is syn to the chloro substituents in the aniline phenyl ring, similar to that observed in N-(2,3-dichlorophenyl)-acetamide (Gowda, Foro, & Fuess, 2007), but in contrast to the anti conformation observed with respect to the ortho-Cl substituent in N-(2-chlorophenyl)-benzamide (Gowda, Sowmya, et al., 2007). The structure resembles the structure of N-(phenyl)-2-chlorobenzamide (Gowda et al., 2003), N-(2-chlorophenyl)-benzamide (Gowda, Sowmya, et al., 2007) and N-(2,3-dichlorophenyl)-acetamide (Gowda, Foro, & Fuess, 2007). The packing diagram showis the infinite chain of molecules along [0 0 1] linked by N—H···O hydrogen bonds (Fig. 2 and Table 2).