3-Chloro-N-(2-methyl­phen­yl)benzamide

In the mol­ecular structure of the title compound, C₁₄H₁₂ClNO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-methyl group in the aniline ring is positioned syn to the N—H bond. The two benzene rings are nearly coplanar [dihedral angle = 3.48 (5)°]. The crystal structure is stabilized by N—H...O hydrogen bonds, which link the mol­ecules into chains along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.098
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          7

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.83 mm
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          !
PLAT931_ALERT_5_G Check Twin Law (       )[ 0 0  1] Estimated BASF       0.07
PLAT931_ALERT_5_G Check Twin Law ( 0 0  1)[       ] Estimated BASF       0.07

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

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S1. Comment

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2000; Rodrigues et al., 2011; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylamides (Gowda et al., 1996), in the present work, the crystal structure of 3-Chloro-N-(2-methylphenyl)- benzamide (I) has been determined (Fig.1).

In (I), the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other. The meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-methyl group in the anilino ring is positioned syn to the N—H bond, in contrast to the syn conformation observed between the meta-Cl atom in the benzoyl ring and the C=O bond in 3-Chloro-N-(3-methylphenyl)benzamide (II) (Rodrigues et al., 2011), while the meta-methyl group in the anilino ring is positioned anti to the N—H bond. Further, the two aromatic rings are nearly coplanar with the dihedral angle of 3.48 (5)°, compared to the value of 77.4 (1)° in (II).

In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the b-axis. Part of the crystal structure is shown in Fig. 2.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2000); Rodrigues et al. (2011); Saeed et al. (2010), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004) on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloroarylamides, see: Gowda et al. (1996).

S2. Experimental

The title compound was prepared according to the method described by 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.

Rod like colorless single crystals of the title compound used in x-ray diffraction studies were obtained by slow evaporation of an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

S3. Refinement

All H atoms were visible in difference maps and then treated as riding atoms with C–H distances of 0.93 Å (C-aromatic), 0.96 Å (C-methyl) and N—H = 0.86 Å. The U_iso(H) values were set at 1.2 U_eq(C-aromatic, N) and 1.5 U_eq(C-methyl).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of the title compound. Molecular chains are generated by N—H···O hydrogen bonds which are shown by dashed lines.

3-Chloro-N-(2-methylphenyl)benzamide

Crystal data

C14H12ClNO	F(000) = 512
Mr = 245.70	Dx = 1.383 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7179 reflections
a = 11.1699 (5) Å	θ = 3.4–26.4°
b = 4.9171 (2) Å	µ = 0.31 mm^−1
c = 21.4778 (8) Å	T = 293 K
β = 90.339 (3)°	Rod, colorless
V = 1179.63 (8) Å^3	0.83 × 0.55 × 0.10 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2411 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2154 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 10.4340 pixels mm^-1	θmax = 26.4°, θmin = 3.4°
ω scans	h = −13→13
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	k = −6→6
Tmin = 0.818, Tmax = 0.970	l = −26→26
22104 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0481P)^2 + 0.4496P] where P = (Fo^2 + 2Fc^2)/3
2411 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.78713 (15)	0.6810 (3)	0.51026 (8)	0.0347 (4)
C2	0.84225 (16)	0.5801 (3)	0.45112 (8)	0.0342 (4)
C3	0.78692 (16)	0.3823 (3)	0.41438 (8)	0.0357 (4)
H3A	0.7150	0.3041	0.4267	0.043*
C4	0.84060 (17)	0.3043 (3)	0.35942 (8)	0.0380 (4)
C5	0.94821 (18)	0.4136 (4)	0.34075 (9)	0.0434 (4)
H5A	0.9839	0.3563	0.3040	0.052*
C6	1.00224 (17)	0.6092 (4)	0.37740 (9)	0.0452 (4)
H6A	1.0750	0.6837	0.3652	0.054*
C7	0.94945 (17)	0.6957 (4)	0.43205 (8)	0.0395 (4)
H7A	0.9856	0.8308	0.4559	0.047*
C8	0.66916 (16)	0.5439 (3)	0.60171 (8)	0.0333 (4)
C9	0.56240 (16)	0.4044 (3)	0.61282 (8)	0.0362 (4)
C10	0.50367 (19)	0.4563 (4)	0.66843 (9)	0.0483 (5)
H10A	0.4327	0.3650	0.6769	0.058*
C11	0.5475 (2)	0.6388 (5)	0.71132 (9)	0.0547 (5)
H11A	0.5059	0.6712	0.7479	0.066*
C12	0.6531 (2)	0.7737 (4)	0.69999 (9)	0.0513 (5)
H12A	0.6831	0.8967	0.7290	0.062*
C13	0.71473 (18)	0.7262 (4)	0.64539 (8)	0.0418 (4)
H13A	0.7865	0.8159	0.6379	0.050*
C14	0.51064 (18)	0.2054 (4)	0.56700 (9)	0.0446 (4)
H14C	0.4336	0.1460	0.5811	0.053*
H14B	0.5630	0.0515	0.5635	0.053*
H14A	0.5022	0.2914	0.5271	0.053*
N1	0.73102 (13)	0.4923 (3)	0.54513 (6)	0.0348 (3)
H1A	0.7328	0.3269	0.5321	0.042*
O1	0.79372 (14)	0.9221 (2)	0.52456 (7)	0.0504 (4)
Cl1	0.77036 (5)	0.06380 (10)	0.31224 (2)	0.05338 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0383 (9)	0.0273 (8)	0.0386 (9)	0.0012 (7)	0.0004 (7)	−0.0005 (7)
C2	0.0385 (9)	0.0286 (8)	0.0356 (8)	0.0035 (7)	0.0020 (7)	0.0037 (6)
C3	0.0392 (9)	0.0319 (8)	0.0361 (8)	−0.0009 (7)	0.0040 (7)	0.0026 (7)
C4	0.0462 (10)	0.0328 (9)	0.0348 (9)	0.0036 (7)	−0.0019 (7)	0.0011 (7)
C5	0.0481 (10)	0.0468 (11)	0.0353 (9)	0.0062 (8)	0.0088 (8)	0.0017 (8)
C6	0.0383 (10)	0.0503 (11)	0.0469 (10)	−0.0025 (8)	0.0074 (8)	0.0069 (9)
C7	0.0415 (9)	0.0370 (9)	0.0401 (9)	−0.0023 (7)	0.0002 (7)	0.0013 (7)
C8	0.0386 (9)	0.0278 (8)	0.0336 (8)	0.0039 (7)	0.0019 (7)	−0.0005 (6)
C9	0.0406 (9)	0.0313 (8)	0.0369 (9)	0.0024 (7)	0.0002 (7)	−0.0004 (7)
C10	0.0485 (11)	0.0481 (11)	0.0484 (11)	−0.0019 (9)	0.0127 (9)	−0.0004 (9)
C11	0.0669 (14)	0.0582 (12)	0.0393 (10)	0.0033 (11)	0.0142 (9)	−0.0078 (9)
C12	0.0666 (13)	0.0481 (11)	0.0392 (10)	0.0016 (10)	−0.0026 (9)	−0.0138 (8)
C13	0.0449 (10)	0.0374 (9)	0.0429 (10)	−0.0016 (8)	−0.0011 (8)	−0.0074 (8)
C14	0.0440 (10)	0.0418 (10)	0.0479 (10)	−0.0062 (8)	0.0002 (8)	−0.0041 (8)
N1	0.0439 (8)	0.0258 (6)	0.0348 (7)	0.0000 (6)	0.0058 (6)	−0.0047 (5)
O1	0.0717 (10)	0.0252 (6)	0.0547 (8)	−0.0019 (6)	0.0158 (7)	−0.0037 (5)
Cl1	0.0666 (3)	0.0502 (3)	0.0434 (3)	−0.0055 (2)	−0.0005 (2)	−0.0113 (2)

Geometric parameters (Å, º)

C1—O1	1.227 (2)	C8—C9	1.398 (3)
C1—N1	1.349 (2)	C8—N1	1.424 (2)
C1—C2	1.499 (2)	C9—C10	1.390 (3)
C2—C7	1.389 (3)	C9—C14	1.501 (2)
C2—C3	1.395 (2)	C10—C11	1.374 (3)
C3—C4	1.381 (2)	C10—H10A	0.9300
C3—H3A	0.9300	C11—C12	1.376 (3)
C4—C5	1.378 (3)	C11—H11A	0.9300
C4—Cl1	1.7412 (18)	C12—C13	1.383 (3)
C5—C6	1.380 (3)	C12—H12A	0.9300
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.384 (3)	C14—H14C	0.9600
C6—H6A	0.9300	C14—H14B	0.9600
C7—H7A	0.9300	C14—H14A	0.9600
C8—C13	1.392 (2)	N1—H1A	0.8600
O1—C1—N1	123.60 (16)	C10—C9—C8	117.66 (17)
O1—C1—C2	120.50 (16)	C10—C9—C14	120.08 (17)
N1—C1—C2	115.91 (14)	C8—C9—C14	122.26 (16)
C7—C2—C3	119.89 (16)	C11—C10—C9	121.86 (19)
C7—C2—C1	118.25 (16)	C11—C10—H10A	119.1
C3—C2—C1	121.82 (16)	C9—C10—H10A	119.1
C4—C3—C2	118.93 (17)	C10—C11—C12	119.91 (18)
C4—C3—H3A	120.5	C10—C11—H11A	120.0
C2—C3—H3A	120.5	C12—C11—H11A	120.0
C5—C4—C3	121.61 (17)	C11—C12—C13	119.99 (18)
C5—C4—Cl1	119.08 (14)	C11—C12—H12A	120.0
C3—C4—Cl1	119.31 (14)	C13—C12—H12A	120.0
C4—C5—C6	119.01 (17)	C12—C13—C8	119.91 (18)
C4—C5—H5A	120.5	C12—C13—H13A	120.0
C6—C5—H5A	120.5	C8—C13—H13A	120.0
C5—C6—C7	120.75 (18)	C9—C14—H14C	109.5
C5—C6—H6A	119.6	C9—C14—H14B	109.5
C7—C6—H6A	119.6	H14C—C14—H14B	109.5
C6—C7—C2	119.78 (17)	C9—C14—H14A	109.5
C6—C7—H7A	120.1	H14C—C14—H14A	109.5
C2—C7—H7A	120.1	H14B—C14—H14A	109.5
C13—C8—C9	120.67 (16)	C1—N1—C8	125.45 (14)
C13—C8—N1	120.84 (16)	C1—N1—H1A	117.3
C9—C8—N1	118.48 (15)	C8—N1—H1A	117.3
O1—C1—C2—C7	36.2 (2)	N1—C8—C9—C10	179.64 (16)
N1—C1—C2—C7	−144.13 (16)	C13—C8—C9—C14	−179.74 (17)
O1—C1—C2—C3	−141.61 (19)	N1—C8—C9—C14	−0.6 (3)
N1—C1—C2—C3	38.0 (2)	C8—C9—C10—C11	0.3 (3)
C7—C2—C3—C4	0.2 (3)	C14—C9—C10—C11	−179.4 (2)
C1—C2—C3—C4	177.98 (15)	C9—C10—C11—C12	−0.7 (3)
C2—C3—C4—C5	1.2 (3)	C10—C11—C12—C13	0.3 (3)
C2—C3—C4—Cl1	−178.37 (13)	C11—C12—C13—C8	0.6 (3)
C3—C4—C5—C6	−1.2 (3)	C9—C8—C13—C12	−1.0 (3)
Cl1—C4—C5—C6	178.37 (15)	N1—C8—C13—C12	179.91 (17)
C4—C5—C6—C7	−0.2 (3)	O1—C1—N1—C8	1.9 (3)
C5—C6—C7—C2	1.6 (3)	C2—C1—N1—C8	−177.71 (15)
C3—C2—C7—C6	−1.5 (3)	C13—C8—N1—C1	−40.0 (3)
C1—C2—C7—C6	−179.42 (16)	C9—C8—N1—C1	140.87 (17)
C13—C8—C9—C10	0.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.11	2.9237 (18)	158

Symmetry code: (i) x, y−1, z.