4-Chloro-benzoic acid-quinoline (1/1).

In the title compound, C(7)H(5)ClO(2)·C(9)H(7)N, the 4-chloro-benzoic acid mol-ecule is almost planar, with a dihedral angle of 2.9 (14)° between the carb-oxy group and the benzene ring. In the crystal, the two components are connected by an O-H⋯N hydrogen bond. In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of the benzoic acid is 44.75 (4)°. The two components are further linked by inter-molecular C-H⋯O hydrogen bonds, forming a layer parallel to the ab plane.

Related literature

For related structures, see, for example: Gotoh & Ishida (2007 ▶, 2009 ▶); Ishida & Fukunaga (2004 ▶).

Experimental

Crystal data

C7H5ClO2·C9H7N

M = 285.73

Orthorhombic,

a = 13.2385 (5) Å

b = 3.8307 (2) Å

c = 26.2464 (9) Å

V = 1331.03 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 185 K

0.30 × 0.26 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.933, T max = 0.950

21775 measured reflections

3907 independent reflections

3777 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.071

S = 1.07

3907 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 1909 Friedel pairs

Flack parameter: 0.03 (4)

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997) ▶; software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046416/im2244sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046416/im2244Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H5ClO2·C9H7N	F(000) = 592.00
Mr = 285.73	Dx = 1.426 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2c -2ac	Cell parameters from 20625 reflections
a = 13.2385 (5) Å	θ = 3.1–30.0°
b = 3.8307 (2) Å	µ = 0.29 mm−1
c = 26.2464 (9) Å	T = 185 K
V = 1331.03 (10) Å3	Block, colorless
Z = 4	0.30 × 0.26 × 0.18 mm

Rigaku R-AXIS RAPID II diffractometer	3777 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1	Rint = 0.017
ω scans	θmax = 30.0°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −18→17
Tmin = 0.933, Tmax = 0.950	k = −5→5
21775 measured reflections	l = −36→36
3907 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.0837P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3907 reflections	Δρmax = 0.29 e Å−3
185 parameters	Δρmin = −0.15 e Å−3
1 restraint	Absolute structure: Flack (1983), 1909 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (4)

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	0.16026 (2)	1.03905 (7)	0.806049 (12)	0.03662 (8)
O1	0.40632 (7)	0.4457 (3)	0.60147 (3)	0.03433 (19)
O2	0.53847 (6)	0.6264 (3)	0.64747 (3)	0.03630 (19)
N1	0.54986 (7)	0.2446 (2)	0.53696 (4)	0.02677 (17)
C1	0.37402 (7)	0.6999 (3)	0.68200 (4)	0.02308 (18)
C2	0.41115 (8)	0.8623 (3)	0.72551 (4)	0.02695 (19)
H2	0.4817	0.9015	0.7289	0.032*
C3	0.34608 (9)	0.9674 (3)	0.76389 (4)	0.0283 (2)
H3	0.3713	1.0796	0.7936	0.034*
C4	0.24300 (9)	0.9056 (3)	0.75818 (4)	0.02659 (19)
C5	0.20408 (8)	0.7420 (3)	0.71540 (4)	0.0284 (2)
H5	0.1336	0.7010	0.7123	0.034*
C6	0.27012 (7)	0.6389 (3)	0.67712 (4)	0.02561 (19)
H6	0.2447	0.5266	0.6475	0.031*
C7	0.44796 (8)	0.5884 (3)	0.64212 (4)	0.02529 (19)
C8	0.63210 (9)	0.1038 (3)	0.55654 (5)	0.0312 (2)
H8	0.6346	0.0685	0.5923	0.037*
C9	0.71666 (9)	0.0024 (3)	0.52725 (5)	0.0323 (2)
H9	0.7742	−0.0989	0.5430	0.039*
C10	0.71388 (8)	0.0531 (3)	0.47574 (5)	0.0297 (2)
H10	0.7696	−0.0144	0.4552	0.036*
C11	0.62751 (7)	0.2070 (3)	0.45316 (4)	0.02400 (18)
C12	0.61876 (9)	0.2723 (3)	0.40025 (4)	0.0304 (2)
H12	0.6730	0.2140	0.3781	0.037*
C13	0.53272 (10)	0.4190 (3)	0.38070 (4)	0.0331 (2)
H13	0.5275	0.4598	0.3451	0.040*
C14	0.45165 (10)	0.5100 (3)	0.41306 (5)	0.0314 (2)
H14	0.3922	0.6106	0.3990	0.038*
C15	0.45801 (8)	0.4545 (3)	0.46454 (5)	0.0272 (2)
H15	0.4035	0.5189	0.4861	0.033*
C16	0.54610 (7)	0.3005 (2)	0.48551 (4)	0.02275 (18)
H1	0.4522 (17)	0.392 (6)	0.5808 (9)	0.061 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.04236 (14)	0.03938 (14)	0.02811 (12)	0.00840 (10)	0.00809 (12)	−0.00104 (13)
O1	0.0260 (4)	0.0509 (5)	0.0261 (4)	−0.0014 (3)	0.0017 (3)	−0.0079 (3)
O2	0.0238 (4)	0.0525 (5)	0.0326 (4)	−0.0001 (4)	−0.0006 (3)	−0.0010 (4)
N1	0.0264 (4)	0.0293 (4)	0.0246 (4)	−0.0015 (3)	0.0013 (3)	−0.0015 (3)
C1	0.0232 (4)	0.0249 (4)	0.0211 (4)	0.0006 (3)	−0.0009 (4)	0.0027 (3)
C2	0.0265 (4)	0.0305 (5)	0.0238 (4)	−0.0040 (4)	−0.0027 (4)	0.0023 (4)
C3	0.0356 (5)	0.0272 (5)	0.0221 (5)	−0.0033 (4)	−0.0037 (4)	0.0006 (4)
C4	0.0332 (5)	0.0246 (4)	0.0220 (4)	0.0041 (4)	0.0035 (4)	0.0021 (3)
C5	0.0251 (5)	0.0320 (5)	0.0280 (5)	0.0017 (4)	−0.0015 (4)	0.0004 (4)
C6	0.0238 (4)	0.0303 (5)	0.0228 (4)	0.0014 (4)	−0.0034 (4)	−0.0003 (4)
C7	0.0255 (5)	0.0281 (4)	0.0222 (4)	0.0013 (4)	−0.0006 (4)	0.0038 (3)
C8	0.0330 (5)	0.0319 (5)	0.0286 (5)	−0.0034 (4)	−0.0030 (4)	0.0018 (4)
C9	0.0260 (5)	0.0303 (5)	0.0406 (7)	0.0021 (4)	−0.0066 (5)	−0.0001 (4)
C10	0.0225 (4)	0.0278 (5)	0.0387 (6)	0.0006 (4)	0.0022 (4)	−0.0047 (4)
C11	0.0220 (4)	0.0229 (4)	0.0271 (4)	−0.0034 (3)	0.0022 (4)	−0.0043 (3)
C12	0.0330 (5)	0.0318 (5)	0.0266 (5)	−0.0053 (4)	0.0060 (4)	−0.0050 (4)
C13	0.0427 (6)	0.0319 (5)	0.0248 (5)	−0.0065 (4)	−0.0016 (5)	0.0007 (4)
C14	0.0325 (5)	0.0290 (5)	0.0328 (6)	−0.0008 (4)	−0.0064 (4)	0.0016 (4)
C15	0.0240 (5)	0.0268 (5)	0.0308 (5)	0.0018 (4)	0.0004 (4)	−0.0016 (4)
C16	0.0228 (4)	0.0210 (4)	0.0245 (4)	−0.0028 (3)	0.0019 (4)	−0.0022 (3)

Cl1—C4	1.7434 (11)	C8—C9	1.4123 (18)
O1—C7	1.3194 (14)	C8—H8	0.9500
O1—H1	0.84 (2)	C9—C10	1.3666 (18)
O2—C7	1.2151 (14)	C9—H9	0.9500
N1—C8	1.3194 (15)	C10—C11	1.4162 (15)
N1—C16	1.3681 (13)	C10—H10	0.9500
C1—C2	1.3903 (14)	C11—C12	1.4160 (15)
C1—C6	1.4010 (14)	C11—C16	1.4179 (13)
C1—C7	1.4953 (14)	C12—C13	1.3697 (18)
C2—C3	1.3854 (16)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.4125 (18)
C3—C4	1.3931 (16)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.3703 (16)
C4—C5	1.3854 (16)	C14—H14	0.9500
C5—C6	1.3891 (15)	C15—C16	1.4180 (14)
C5—H5	0.9500	C15—H15	0.9500
C6—H6	0.9500
C7—O1—H1	108.7 (15)	C9—C8—H8	118.2
C8—N1—C16	118.58 (10)	C10—C9—C8	118.55 (11)
C2—C1—C6	119.79 (9)	C10—C9—H9	120.7
C2—C1—C7	118.11 (9)	C8—C9—H9	120.7
C6—C1—C7	122.08 (9)	C9—C10—C11	119.66 (10)
C3—C2—C1	120.50 (10)	C9—C10—H10	120.2
C3—C2—H2	119.8	C11—C10—H10	120.2
C1—C2—H2	119.8	C12—C11—C10	123.36 (10)
C2—C3—C4	118.78 (10)	C12—C11—C16	118.71 (10)
C2—C3—H3	120.6	C10—C11—C16	117.92 (10)
C4—C3—H3	120.6	C13—C12—C11	120.53 (10)
C5—C4—C3	121.90 (10)	C13—C12—H12	119.7
C5—C4—Cl1	118.89 (9)	C11—C12—H12	119.7
C3—C4—Cl1	119.21 (9)	C12—C13—C14	120.52 (11)
C4—C5—C6	118.74 (10)	C12—C13—H13	119.7
C4—C5—H5	120.6	C14—C13—H13	119.7
C6—C5—H5	120.6	C15—C14—C13	120.52 (11)
C5—C6—C1	120.29 (10)	C15—C14—H14	119.7
C5—C6—H6	119.9	C13—C14—H14	119.7
C1—C6—H6	119.9	C14—C15—C16	119.86 (11)
O2—C7—O1	123.72 (11)	C14—C15—H15	120.1
O2—C7—C1	122.03 (10)	C16—C15—H15	120.1
O1—C7—C1	114.25 (9)	N1—C16—C11	121.59 (9)
N1—C8—C9	123.68 (11)	N1—C16—C15	118.55 (9)
N1—C8—H8	118.2	C11—C16—C15	119.85 (9)
C6—C1—C2—C3	−0.61 (16)	C8—C9—C10—C11	0.47 (17)
C7—C1—C2—C3	−179.29 (10)	C9—C10—C11—C12	179.31 (11)
C1—C2—C3—C4	0.35 (16)	C9—C10—C11—C16	−0.50 (15)
C2—C3—C4—C5	0.13 (16)	C10—C11—C12—C13	179.38 (10)
C2—C3—C4—Cl1	−179.61 (8)	C16—C11—C12—C13	−0.81 (15)
C3—C4—C5—C6	−0.34 (16)	C11—C12—C13—C14	0.51 (17)
Cl1—C4—C5—C6	179.40 (8)	C12—C13—C14—C15	0.29 (18)
C4—C5—C6—C1	0.07 (16)	C13—C14—C15—C16	−0.77 (17)
C2—C1—C6—C5	0.40 (16)	C8—N1—C16—C11	0.75 (15)
C7—C1—C6—C5	179.02 (10)	C8—N1—C16—C15	−179.50 (10)
C2—C1—C7—O2	2.21 (16)	C12—C11—C16—N1	−179.93 (9)
C6—C1—C7—O2	−176.43 (11)	C10—C11—C16—N1	−0.11 (14)
C2—C1—C7—O1	−178.14 (10)	C12—C11—C16—C15	0.33 (14)
C6—C1—C7—O1	3.21 (14)	C10—C11—C16—C15	−179.85 (9)
C16—N1—C8—C9	−0.81 (17)	C14—C15—C16—N1	−179.29 (10)
N1—C8—C9—C10	0.20 (18)	C14—C15—C16—C11	0.45 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84 (2)	1.82 (2)	2.659 (1)	176 (2)
C5—H5···O2i	0.95	2.46	3.159 (1)	130
C8—H8···O2ii	0.95	2.57	3.252 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84 (2)	1.82 (2)	2.659 (1)	176 (2)
C5—H5⋯O2i	0.95	2.46	3.159 (1)	130
C8—H8⋯O2ii	0.95	2.57	3.252 (2)	129

Symmetry codes: (i) ; (ii) .