Crystal structure of 2-(4-chloro-benzamido)-benzoic acid.

In the title mol-ecule, C14H10ClNO3, the amide C=O bond is anti to the o-carb-oxy substituent in the adjacent benzene ring, a conformation that facilitates the formation of an intra-molecular amide-N-H⋯O(carbon-yl) hydrogen bond that closes an S(6) loop. The central amide segment is twisted away from the carb-oxy- and chloro-substituted benzene rings by 13.93 (17) and 15.26 (15)°, respectively. The most prominent supra-molecular inter-actions in the crystal packing are carb-oxy-lic acid-H⋯O(carbox-yl) hydrogen bonds that lead to centrosymmetric dimeric aggregates connected by eight-membered {⋯HOC=O}2 synthons.

Related literature

For our studies on the effects of substituents on the structures of N-(ar­yl)-amides, see: Moreno-Fuquen et al. (2014 ▸, 2015 ▸). For benzanilide properties, see: Nuta et al. (2013 ▸); Leander (1992 ▸); Ahles et al. (2004 ▸). For related structures, see: Saeed et al. (2008 ▸, 2010 ▸); Rodrigues et al. (2011 ▸). For hydrogen bonding, see: Desiraju & Steiner (1999 ▸), Nardelli (1995 ▸).

Experimental

Crystal data

C14H10ClNO3

M = 275.69

Monoclinic

a = 26.8843 (10) Å

b = 5.0367 (2) Å

c = 20.9264 (12) Å

β = 117.489 (2)°

V = 2513.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 295 K

0.40 × 0.08 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

4248 measured reflections

2295 independent reflections

1049 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.132

S = 0.92

2295 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Nonius, 2000 ▸); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ▸); data reduction: HKL DENZO (Otwinowski & Minor, 1997 ▸) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2006 ▸); software used to prepare material for publication: SHELXL2014/7.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015017879/tk5391sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017879/tk5391Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015017879/tk5391Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015017879/tk5391fig1.tif

The mol­ecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

CCDC reference: 1427117

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H10ClNO3	Dx = 1.457 Mg m−3
Mr = 275.69	Melting point: 470(1) K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.8843 (10) Å	Cell parameters from 2553 reflections
b = 5.0367 (2) Å	θ = 3.1–25.4°
c = 20.9264 (12) Å	µ = 0.31 mm−1
β = 117.489 (2)°	T = 295 K
V = 2513.7 (2) Å3	Needle, yellow
Z = 8	0.40 × 0.08 × 0.06 mm
F(000) = 1136

Nonius KappaCCD diffractometer	1049 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 25.4°, θmin = 3.1°
CCD rotation images, thick slices scans	h = −31→32
4248 measured reflections	k = −6→6
2295 independent reflections	l = −25→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ2(Fo2) + (0.0632P)2] where P = (Fo2 + 2Fc2)/3
2295 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.74640 (9)	−0.2731 (4)	0.30942 (12)	0.0824 (7)
C5	0.90834 (14)	−0.0840 (7)	0.34839 (18)	0.0786 (9)
H5	0.9265	−0.1847	0.3282	0.094*
C10	0.58970 (13)	−0.0955 (6)	0.29315 (17)	0.0739 (9)
H10	0.5647	−0.2205	0.2623	0.089*
C9	0.64347 (12)	−0.0846 (5)	0.30083 (15)	0.0623 (8)
H9	0.6543	−0.2008	0.2750	0.075*
C2	0.85453 (13)	0.2133 (6)	0.40771 (18)	0.0766 (9)
H2	0.8366	0.3155	0.4280	0.092*
C11	0.57224 (13)	0.0750 (6)	0.33029 (18)	0.0754 (9)
H11	0.5357	0.0667	0.3242	0.090*
C6	0.85319 (14)	−0.1349 (6)	0.33124 (17)	0.0730 (9)
H6	0.8344	−0.2716	0.2993	0.088*
C3	0.90974 (14)	0.2649 (6)	0.42543 (18)	0.0801 (10)
H3	0.9289	0.4004	0.4577	0.096*
C4	0.93606 (13)	0.1173 (7)	0.39566 (17)	0.0701 (9)
NH1	0.7536 (13)	0.280 (6)	0.3758 (17)	0.102 (11)*
Cl1	1.00534 (4)	0.1835 (2)	0.41722 (6)	0.1062 (4)
N1	0.73632 (10)	0.1205 (5)	0.35559 (12)	0.0592 (7)
O3	0.67865 (8)	0.6206 (3)	0.46790 (10)	0.0688 (6)
OH3	0.7015	0.7286	0.4949	0.103*
O2	0.75129 (8)	0.5079 (3)	0.45041 (10)	0.0641 (6)
C14	0.70192 (12)	0.4755 (5)	0.43671 (14)	0.0548 (7)
C8	0.68169 (11)	0.1015 (5)	0.34751 (14)	0.0529 (7)
C7	0.76554 (12)	−0.0609 (6)	0.33845 (15)	0.0599 (7)
C13	0.66432 (11)	0.2748 (5)	0.38605 (14)	0.0535 (7)
C1	0.82537 (12)	0.0120 (5)	0.36030 (15)	0.0568 (7)
C12	0.60946 (12)	0.2573 (6)	0.37640 (15)	0.0664 (8)
H12	0.5979	0.3718	0.4018	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0839 (16)	0.0631 (13)	0.1073 (17)	−0.0111 (11)	0.0502 (14)	−0.0225 (12)
C5	0.075 (2)	0.090 (2)	0.083 (2)	0.0100 (19)	0.047 (2)	−0.004 (2)
C10	0.063 (2)	0.071 (2)	0.072 (2)	−0.0093 (16)	0.0174 (18)	0.0023 (17)
C9	0.063 (2)	0.0595 (17)	0.0591 (19)	−0.0054 (15)	0.0242 (16)	−0.0031 (15)
C2	0.066 (2)	0.081 (2)	0.090 (2)	−0.0010 (17)	0.0417 (18)	−0.0156 (19)
C11	0.056 (2)	0.083 (2)	0.083 (2)	−0.0118 (18)	0.0279 (18)	−0.0009 (19)
C6	0.080 (2)	0.072 (2)	0.074 (2)	0.0010 (17)	0.0420 (19)	−0.0089 (16)
C3	0.066 (2)	0.085 (2)	0.089 (2)	−0.0102 (17)	0.035 (2)	−0.0121 (19)
C4	0.0581 (19)	0.083 (2)	0.073 (2)	0.0059 (17)	0.0343 (17)	0.0122 (18)
Cl1	0.0657 (6)	0.1390 (9)	0.1189 (8)	0.0021 (5)	0.0469 (6)	0.0093 (6)
N1	0.0576 (16)	0.0555 (15)	0.0681 (16)	−0.0068 (13)	0.0322 (13)	−0.0118 (13)
O3	0.0622 (13)	0.0726 (12)	0.0763 (13)	−0.0053 (10)	0.0360 (11)	−0.0183 (11)
O2	0.0560 (13)	0.0685 (12)	0.0694 (13)	−0.0070 (10)	0.0304 (11)	−0.0138 (10)
C14	0.0581 (19)	0.0553 (17)	0.0522 (18)	0.0026 (15)	0.0264 (16)	0.0028 (14)
C8	0.0513 (17)	0.0527 (15)	0.0506 (16)	−0.0041 (13)	0.0202 (14)	0.0055 (14)
C7	0.068 (2)	0.0570 (18)	0.0555 (18)	0.0000 (16)	0.0298 (16)	0.0024 (15)
C13	0.0515 (17)	0.0564 (16)	0.0514 (17)	−0.0007 (14)	0.0228 (14)	0.0040 (14)
C1	0.0608 (19)	0.0581 (17)	0.0554 (18)	0.0033 (15)	0.0302 (16)	0.0025 (14)
C12	0.0564 (19)	0.074 (2)	0.071 (2)	−0.0005 (16)	0.0314 (16)	0.0024 (16)

O1—C7	1.219 (3)	C6—H6	0.9300
C5—C4	1.371 (4)	C3—C4	1.360 (4)
C5—C6	1.379 (4)	C3—H3	0.9300
C5—H5	0.9300	C4—Cl1	1.734 (3)
C10—C11	1.378 (4)	N1—C7	1.357 (3)
C10—C9	1.380 (4)	N1—C8	1.402 (3)
C10—H10	0.9300	N1—NH1	0.93 (3)
C9—C8	1.401 (4)	O3—C14	1.315 (3)
C9—H9	0.9300	O3—OH3	0.8200
C2—C3	1.378 (4)	O2—C14	1.233 (3)
C2—C1	1.382 (4)	C14—C13	1.476 (4)
C2—H2	0.9300	C8—C13	1.406 (4)
C11—C12	1.373 (4)	C7—C1	1.501 (4)
C11—H11	0.9300	C13—C12	1.396 (4)
C6—C1	1.377 (4)	C12—H12	0.9300
C4—C5—C6	119.1 (3)	C5—C4—Cl1	119.4 (3)
C4—C5—H5	120.5	C7—N1—C8	128.6 (3)
C6—C5—H5	120.5	C7—N1—NH1	118 (2)
C11—C10—C9	121.4 (3)	C8—N1—NH1	113 (2)
C11—C10—H10	119.3	C14—O3—OH3	109.5
C9—C10—H10	119.3	O2—C14—O3	121.3 (3)
C10—C9—C8	120.0 (3)	O2—C14—C13	124.4 (3)
C10—C9—H9	120.0	O3—C14—C13	114.3 (3)
C8—C9—H9	120.0	C9—C8—N1	121.3 (3)
C3—C2—C1	121.0 (3)	C9—C8—C13	119.0 (3)
C3—C2—H2	119.5	N1—C8—C13	119.7 (2)
C1—C2—H2	119.5	O1—C7—N1	124.0 (3)
C12—C11—C10	119.1 (3)	O1—C7—C1	120.8 (3)
C12—C11—H11	120.5	N1—C7—C1	115.1 (3)
C10—C11—H11	120.5	C12—C13—C8	119.1 (3)
C1—C6—C5	121.5 (3)	C12—C13—C14	118.3 (3)
C1—C6—H6	119.2	C8—C13—C14	122.6 (3)
C5—C6—H6	119.2	C6—C1—C2	117.9 (3)
C4—C3—C2	119.8 (3)	C6—C1—C7	117.3 (3)
C4—C3—H3	120.1	C2—C1—C7	124.9 (3)
C2—C3—H3	120.1	C11—C12—C13	121.5 (3)
C3—C4—C5	120.7 (3)	C11—C12—H12	119.2
C3—C4—Cl1	119.9 (3)	C13—C12—H12	119.2
C11—C10—C9—C8	0.4 (4)	N1—C8—C13—C14	−1.4 (4)
C9—C10—C11—C12	−0.7 (5)	O2—C14—C13—C12	179.1 (3)
C4—C5—C6—C1	0.2 (5)	O3—C14—C13—C12	−0.2 (3)
C1—C2—C3—C4	0.4 (5)	O2—C14—C13—C8	−0.8 (4)
C2—C3—C4—C5	−0.4 (5)	O3—C14—C13—C8	179.9 (2)
C2—C3—C4—Cl1	179.4 (2)	C5—C6—C1—C2	−0.2 (4)
C6—C5—C4—C3	0.1 (5)	C5—C6—C1—C7	−179.6 (3)
C6—C5—C4—Cl1	−179.7 (2)	C3—C2—C1—C6	−0.1 (4)
C10—C9—C8—N1	−178.9 (2)	C3—C2—C1—C7	179.3 (3)
C10—C9—C8—C13	0.1 (4)	O1—C7—C1—C6	15.5 (4)
C7—N1—C8—C9	−18.7 (4)	N1—C7—C1—C6	−166.6 (2)
C7—N1—C8—C13	162.3 (3)	O1—C7—C1—C2	−163.9 (3)
C8—N1—C7—O1	3.2 (5)	N1—C7—C1—C2	14.0 (4)
C8—N1—C7—C1	−174.6 (2)	C10—C11—C12—C13	0.4 (4)
C9—C8—C13—C12	−0.3 (4)	C8—C13—C12—C11	0.1 (4)
N1—C8—C13—C12	178.7 (2)	C14—C13—C12—C11	−179.8 (2)
C9—C8—C13—C14	179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—NH1···O2	0.93 (3)	1.96 (3)	2.678 (3)	133 (3)
O3—OH3···O2i	0.82	1.83	2.645 (3)	175

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1NH1O2	0.93(3)	1.96(3)	2.678(3)	133(3)
O3OH3O2i	0.82	1.83	2.645(3)	175

Symmetry code: (i) .