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In the structure of the title compound (N2CPBA), C13H10ClNO, the conformation of the N—H bond is anti to the ortho-Cl substituent in the aniline benzene ring. It closely resembles the structure of 2-chloro-N-phenyl­benzamide (NP2CBA), although the two amides crystallize in different crystal systems. The mol­ecules of N2CPBA are linked into a chain through an N—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022878/kp2106sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022878/kp2106Isup2.hkl
Contains datablock I

CCDC reference: 651441

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.051
  • wR factor = 0.171
  • Data-to-parameter ratio = 14.6

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Comment top

In the present work, the structure of N-(2-chlorophenyl)-benzamide (N2CPBA) has been determined to explore the substituent effects on the structure of N-aromatic amides (Gowda et al., 2003; 2007a-d). In the structure of N2CPBA the N—H bond is anti to the ortho-Cl substituent in the aniline phenyl ring (Fig. 1). The structure of N2CPBA closely resembles the structure of N-(phenyl)-2-chlorobenzamide (NP2CBA) (Gowda et al., 2003), although the two amides, N2CPBA and NP2CBA crystallize in different crystal systems: orthorhombic Pbca and tetragonal P43 space groups, respectively. The packing diagram of N2CPBA molecules showing the hydrogen bonds N1—H1N···O1i, generating a chain along [010] [symmetry operation (i): -x + 1/2, y + 1/2, z] (Table 1, Fig. 2).

Related literature top

For related literature, see: Gowda et al. (2003); Gowda, Foro & Fuess (2007); Gowda, Kozisek, Svoboda & Fuess (2007); Gowda et al. (2007a, 2007b).

Experimental top

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

Refinement top

H atoms were placed geometrically and refined using a riding model with C—H distances 0.93 Å for the ring H atoms, and N—H 0.86Å for the NH hydrogen atom.

Structure description top

In the present work, the structure of N-(2-chlorophenyl)-benzamide (N2CPBA) has been determined to explore the substituent effects on the structure of N-aromatic amides (Gowda et al., 2003; 2007a-d). In the structure of N2CPBA the N—H bond is anti to the ortho-Cl substituent in the aniline phenyl ring (Fig. 1). The structure of N2CPBA closely resembles the structure of N-(phenyl)-2-chlorobenzamide (NP2CBA) (Gowda et al., 2003), although the two amides, N2CPBA and NP2CBA crystallize in different crystal systems: orthorhombic Pbca and tetragonal P43 space groups, respectively. The packing diagram of N2CPBA molecules showing the hydrogen bonds N1—H1N···O1i, generating a chain along [010] [symmetry operation (i): -x + 1/2, y + 1/2, z] (Table 1, Fig. 2).

For related literature, see: Gowda et al. (2003); Gowda, Foro & Fuess (2007); Gowda, Kozisek, Svoboda & Fuess (2007); Gowda et al. (2007a, 2007b).

Computing details top

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 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Detail of crystal packing showing the hydrogen bonds N1—H1N···O1 generating a chain along [010] [symmetry operation: (i) -x + 1/2, y + 1/2, z].
N-(2-Chlorophenyl)benzamide top
Crystal data top
C13H10ClNOF(000) = 960
Mr = 231.67Dx = 1.346 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3908 reflections
a = 8.1122 (2) Åθ = 3.2–29.5°
b = 9.3093 (2) ŵ = 0.31 mm1
c = 30.2818 (8) ÅT = 295 K
V = 2286.85 (10) Å3Prism, colourless
Z = 80.44 × 0.10 × 0.10 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer
2224 independent reflections
Graphite monochromator1630 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1Rint = 0.022
φ scans, and ω scans with κ offsetsθmax = 26.0°, θmin = 5.0°
Absorption correction: analytical
(Clark & Reid, 1995)
h = 99
Tmin = 0.879, Tmax = 0.994k = 1111
23061 measured reflectionsl = 3737
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.099P)2 + 0.48P]
where P = (Fo2 + 2Fc2)/3
2224 reflections(Δ/σ)max = 0.01
152 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C13H10ClNOV = 2286.85 (10) Å3
Mr = 231.67Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 8.1122 (2) ŵ = 0.31 mm1
b = 9.3093 (2) ÅT = 295 K
c = 30.2818 (8) Å0.44 × 0.10 × 0.10 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer
2224 independent reflections
Absorption correction: analytical
(Clark & Reid, 1995)
1630 reflections with I > 2σ(I)
Tmin = 0.879, Tmax = 0.994Rint = 0.022
23061 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.171H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.24 e Å3
2224 reflectionsΔρmin = 0.37 e Å3
152 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
xyzUiso*/Ueq
Cl10.15606 (9)0.39267 (9)0.45504 (2)0.0871 (3)
O10.16921 (19)0.36964 (15)0.35146 (6)0.0637 (5)
N10.2540 (2)0.58328 (16)0.37875 (6)0.0528 (5)
H1N0.23640.67430.37990.063*
C10.1565 (2)0.5005 (2)0.35303 (6)0.0476 (5)
C20.0327 (2)0.57676 (19)0.32524 (6)0.0463 (5)
C30.0134 (3)0.5129 (2)0.28601 (7)0.0555 (5)
H30.035 (3)0.423 (3)0.2796 (8)0.067*
C40.1259 (3)0.5798 (3)0.25857 (8)0.0644 (6)
H40.15420.53780.23180.077*
C50.1957 (3)0.7079 (3)0.27083 (9)0.0704 (7)
H50.27240.7520.25250.085*
C60.1530 (3)0.7706 (3)0.30982 (10)0.0726 (7)
H60.20160.85690.31810.087*
C70.0373 (3)0.7065 (2)0.33722 (8)0.0606 (6)
H70.010 (3)0.750 (3)0.3651 (9)0.073*
C80.3846 (3)0.5237 (2)0.40398 (6)0.0511 (5)
C90.3559 (3)0.4297 (2)0.43837 (7)0.0590 (6)
C100.4858 (4)0.3669 (3)0.46060 (9)0.0776 (7)
H100.46480.30070.48290.093*
C110.6447 (4)0.4011 (3)0.45009 (10)0.0819 (8)
H110.73170.35810.46510.098*
C120.6751 (3)0.4993 (3)0.41732 (10)0.0781 (8)
H120.7830.52510.41060.094*
C130.5455 (3)0.5601 (3)0.39423 (8)0.0660 (6)
H130.5670.62610.37190.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0785 (5)0.1082 (7)0.0747 (5)0.0152 (3)0.0059 (3)0.0285 (4)
O10.0778 (11)0.0361 (8)0.0771 (11)0.0031 (6)0.0165 (8)0.0041 (6)
N10.0603 (10)0.0347 (8)0.0634 (10)0.0006 (7)0.0096 (8)0.0067 (7)
C10.0520 (10)0.0375 (10)0.0534 (11)0.0006 (7)0.0015 (8)0.0060 (8)
C20.0462 (10)0.0385 (9)0.0541 (10)0.0032 (7)0.0021 (8)0.0085 (8)
C30.0528 (11)0.0469 (11)0.0670 (13)0.0038 (9)0.0023 (9)0.0007 (9)
C40.0628 (13)0.0671 (14)0.0634 (13)0.0115 (10)0.0128 (10)0.0036 (11)
C50.0667 (13)0.0571 (14)0.0875 (16)0.0012 (11)0.0243 (12)0.0165 (12)
C60.0749 (15)0.0500 (12)0.0930 (17)0.0143 (10)0.0166 (12)0.0027 (12)
C70.0662 (13)0.0479 (11)0.0678 (13)0.0069 (9)0.0089 (10)0.0018 (10)
C80.0581 (11)0.0396 (10)0.0556 (11)0.0012 (8)0.0048 (8)0.0017 (8)
C90.0661 (13)0.0558 (13)0.0552 (12)0.0026 (9)0.0056 (9)0.0056 (10)
C100.0890 (19)0.0765 (16)0.0673 (15)0.0076 (14)0.0182 (13)0.0206 (12)
C110.0736 (18)0.087 (2)0.0855 (19)0.0151 (13)0.0237 (14)0.0040 (15)
C120.0573 (13)0.0841 (18)0.0928 (19)0.0010 (12)0.0082 (12)0.0025 (15)
C130.0643 (14)0.0599 (13)0.0739 (14)0.0082 (10)0.0031 (11)0.0062 (11)
Geometric parameters (Å, º) top
Cl1—C91.733 (2)C6—C71.387 (3)
O1—C11.224 (2)C6—H60.93
N1—C11.351 (3)C7—H70.96 (3)
N1—C81.419 (3)C8—C91.379 (3)
N1—H1N0.86C8—C131.381 (3)
C1—C21.490 (3)C9—C101.380 (3)
C2—C31.380 (3)C10—C111.365 (4)
C2—C71.383 (3)C10—H100.93
C3—C41.382 (3)C11—C121.372 (4)
C3—H30.95 (3)C11—H110.93
C4—C51.372 (4)C12—C131.383 (4)
C4—H40.93C12—H120.93
C5—C61.362 (4)C13—H130.93
C5—H50.93
C1—N1—C8121.61 (16)C2—C7—C6119.8 (2)
C1—N1—H1N119.2C2—C7—H7120.3 (15)
C8—N1—H1N119.2C6—C7—H7119.8 (15)
O1—C1—N1122.76 (18)C9—C8—C13118.5 (2)
O1—C1—C2120.59 (18)C9—C8—N1121.90 (19)
N1—C1—C2116.64 (16)C13—C8—N1119.65 (18)
C3—C2—C7119.37 (19)C8—C9—C10120.6 (2)
C3—C2—C1117.64 (17)C8—C9—Cl1120.24 (17)
C7—C2—C1122.99 (18)C10—C9—Cl1119.18 (19)
C2—C3—C4120.2 (2)C11—C10—C9120.5 (2)
C2—C3—H3116.5 (15)C11—C10—H10119.7
C4—C3—H3123.3 (15)C9—C10—H10119.7
C5—C4—C3120.1 (2)C10—C11—C12119.6 (2)
C5—C4—H4120C10—C11—H11120.2
C3—C4—H4120C12—C11—H11120.2
C6—C5—C4120.1 (2)C11—C12—C13120.1 (2)
C6—C5—H5119.9C11—C12—H12119.9
C4—C5—H5119.9C13—C12—H12119.9
C5—C6—C7120.4 (2)C8—C13—C12120.7 (2)
C5—C6—H6119.8C8—C13—H13119.7
C7—C6—H6119.8C12—C13—H13119.7
C8—N1—C1—O13.6 (3)C1—N1—C8—C965.3 (3)
C8—N1—C1—C2175.03 (17)C1—N1—C8—C13114.8 (2)
O1—C1—C2—C327.7 (3)C13—C8—C9—C104.0 (3)
N1—C1—C2—C3151.00 (19)N1—C8—C9—C10176.1 (2)
O1—C1—C2—C7151.9 (2)C13—C8—C9—Cl1174.40 (18)
N1—C1—C2—C729.4 (3)N1—C8—C9—Cl15.5 (3)
C7—C2—C3—C41.4 (3)C8—C9—C10—C112.6 (4)
C1—C2—C3—C4179.02 (19)Cl1—C9—C10—C11175.8 (2)
C2—C3—C4—C51.9 (3)C9—C10—C11—C120.4 (5)
C3—C4—C5—C60.8 (4)C10—C11—C12—C131.9 (4)
C4—C5—C6—C70.7 (4)C9—C8—C13—C122.5 (4)
C3—C2—C7—C60.1 (3)N1—C8—C13—C12177.6 (2)
C1—C2—C7—C6179.4 (2)C11—C12—C13—C80.4 (4)
C5—C6—C7—C21.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.862.152.860 (2)139
Symmetry code: (i) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC13H10ClNO
Mr231.67
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)295
a, b, c (Å)8.1122 (2), 9.3093 (2), 30.2818 (8)
V3)2286.85 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.44 × 0.10 × 0.10
Data collection
DiffractometerOxford Diffraction Xcalibur
Absorption correctionAnalytical
(Clark & Reid, 1995)
Tmin, Tmax0.879, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
23061, 2224, 1630
Rint0.022
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.171, 1.11
No. of reflections2224
No. of parameters152
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.37

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.862.152.860 (2)139.3
Symmetry code: (i) x+1/2, y+1/2, z.
 

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