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

In the title compound, C(7)H(4)ClNO(4)·C(9)H(7)N, 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 benzoic acid is 3.15 (7)°. In the crystal, units are linked by inter-molecular C-H⋯O hydrogen bonds, forming a tape along the c axis. The tapes are stacked along the b axis through a C-H⋯O hydrogen bond into a layer parallel to the bc plane.

Related literature

For related structures, see: Gotoh & Ishida (2009 ▶); Gotoh et al. (2010 ▶).

Experimental

Crystal data

C9H7N·C7H4ClNO4

M = 330.73

Orthorhombic,

a = 31.125 (3) Å

b = 3.7560 (3) Å

c = 12.3615 (12) Å

V = 1445.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 185 K

0.35 × 0.22 × 0.06 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.925, T max = 0.983

17044 measured reflections

4166 independent reflections

3681 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.083

S = 1.06

4166 reflections

212 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1989 Friedel pairs

Flack parameter: 0.01 (5)

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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104075X/lh5345sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104075X/lh5345Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104075X/lh5345Isup3.cml

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

C9H7N·C7H4ClNO4	F(000) = 680.00
Mr = 330.73	Dx = 1.520 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2c -2ac	Cell parameters from 13096 reflections
a = 31.125 (3) Å	θ = 3.1–29.9°
b = 3.7560 (3) Å	µ = 0.29 mm−1
c = 12.3615 (12) Å	T = 185 K
V = 1445.1 (2) Å3	Platelet, colorless
Z = 4	0.35 × 0.22 × 0.06 mm

Rigaku R-AXIS RAPID II diffractometer	3681 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1	Rint = 0.053
ω scans	θmax = 29.9°, θmin = 3.1°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −42→43
Tmin = 0.925, Tmax = 0.983	k = −4→5
17044 measured reflections	l = −17→17
4166 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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0315P)2 + 0.3405P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.002
4166 reflections	Δρmax = 0.23 e Å−3
212 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 1989 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (5)

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	0.543417 (13)	0.59426 (12)	0.23410 (4)	0.02675 (10)
O1	0.45038 (4)	0.5860 (4)	0.48865 (12)	0.0318 (3)
O2	0.45582 (4)	0.8025 (5)	0.32051 (12)	0.0388 (4)
O3	0.67381 (4)	0.9928 (5)	0.46192 (13)	0.0456 (4)
O4	0.65022 (5)	1.2634 (5)	0.60477 (13)	0.0426 (4)
N1	0.64473 (5)	1.0872 (5)	0.52256 (13)	0.0292 (4)
N2	0.37038 (5)	0.4475 (4)	0.44710 (14)	0.0263 (3)
C1	0.51745 (5)	0.8089 (5)	0.43578 (14)	0.0201 (3)
C2	0.55126 (5)	0.7634 (5)	0.36266 (14)	0.0193 (3)
C3	0.59320 (5)	0.8484 (5)	0.39161 (14)	0.0215 (3)
H3	0.6163	0.8124	0.3427	0.026*
C4	0.60026 (5)	0.9870 (5)	0.49371 (15)	0.0219 (3)
C5	0.56809 (6)	1.0347 (5)	0.56935 (14)	0.0238 (4)
H5	0.5741	1.1294	0.6390	0.029*
C6	0.52678 (6)	0.9388 (5)	0.53943 (14)	0.0230 (4)
H6	0.5042	0.9618	0.5906	0.028*
C7	0.47115 (6)	0.7299 (5)	0.40757 (15)	0.0237 (4)
C8	0.36085 (7)	0.3048 (5)	0.35296 (17)	0.0303 (4)
H8	0.3834	0.2672	0.3024	0.036*
C9	0.31878 (7)	0.2050 (5)	0.32333 (16)	0.0312 (4)
H9	0.3132	0.1036	0.2543	0.037*
C10	0.28633 (6)	0.2568 (5)	0.39549 (16)	0.0276 (4)
H10	0.2579	0.1874	0.3775	0.033*
C11	0.29493 (5)	0.4134 (5)	0.49705 (15)	0.0223 (4)
C12	0.26293 (6)	0.4842 (5)	0.57556 (16)	0.0280 (4)
H12	0.2338	0.4248	0.5610	0.034*
C13	0.27357 (7)	0.6361 (5)	0.67138 (17)	0.0322 (4)
H13	0.2518	0.6830	0.7232	0.039*
C14	0.31654 (7)	0.7255 (5)	0.69516 (18)	0.0325 (4)
H14	0.3235	0.8291	0.7631	0.039*
C15	0.34829 (6)	0.6641 (5)	0.62122 (16)	0.0280 (4)
H15	0.3771	0.7274	0.6375	0.034*
C16	0.33828 (5)	0.5067 (5)	0.52058 (14)	0.0216 (4)
H1	0.4212 (11)	0.530 (9)	0.475 (3)	0.092 (11)*

	U11	U22	U33	U12	U13	U23
Cl1	0.03042 (19)	0.0318 (2)	0.01799 (17)	0.00371 (18)	−0.00209 (19)	−0.00441 (19)
O1	0.0202 (6)	0.0471 (9)	0.0279 (7)	−0.0040 (6)	0.0009 (5)	0.0086 (7)
O2	0.0261 (6)	0.0614 (10)	0.0289 (8)	−0.0008 (7)	−0.0046 (6)	0.0121 (8)
O3	0.0224 (6)	0.0755 (12)	0.0389 (9)	−0.0026 (7)	0.0008 (6)	0.0006 (8)
O4	0.0397 (8)	0.0547 (10)	0.0332 (8)	−0.0134 (8)	−0.0120 (7)	−0.0041 (7)
N1	0.0250 (7)	0.0365 (10)	0.0261 (8)	−0.0057 (7)	−0.0072 (6)	0.0073 (7)
N2	0.0203 (7)	0.0288 (8)	0.0298 (8)	0.0012 (6)	0.0013 (6)	0.0033 (7)
C1	0.0207 (8)	0.0200 (8)	0.0197 (8)	0.0023 (6)	0.0009 (6)	0.0028 (7)
C2	0.0249 (8)	0.0183 (8)	0.0148 (7)	0.0020 (7)	−0.0011 (6)	−0.0005 (6)
C3	0.0198 (7)	0.0256 (9)	0.0191 (8)	0.0023 (7)	0.0025 (6)	0.0032 (7)
C4	0.0205 (7)	0.0230 (8)	0.0222 (8)	−0.0011 (7)	−0.0039 (6)	0.0031 (7)
C5	0.0316 (9)	0.0224 (9)	0.0175 (8)	0.0014 (7)	−0.0028 (7)	0.0001 (7)
C6	0.0248 (8)	0.0253 (10)	0.0191 (8)	0.0010 (7)	0.0039 (6)	0.0010 (7)
C7	0.0225 (8)	0.0278 (10)	0.0209 (9)	0.0019 (7)	0.0005 (7)	0.0015 (7)
C8	0.0316 (9)	0.0298 (10)	0.0295 (10)	0.0043 (8)	0.0055 (8)	0.0010 (8)
C9	0.0392 (10)	0.0291 (10)	0.0254 (10)	−0.0019 (8)	−0.0026 (8)	−0.0027 (8)
C10	0.0264 (9)	0.0254 (9)	0.0309 (10)	−0.0042 (8)	−0.0049 (8)	0.0006 (8)
C11	0.0207 (7)	0.0193 (9)	0.0269 (9)	0.0014 (6)	−0.0015 (7)	0.0023 (7)
C12	0.0221 (8)	0.0240 (9)	0.0380 (11)	0.0002 (7)	0.0036 (7)	0.0029 (9)
C13	0.0356 (10)	0.0273 (10)	0.0337 (11)	0.0023 (8)	0.0104 (8)	0.0011 (8)
C14	0.0455 (11)	0.0268 (10)	0.0252 (9)	−0.0019 (9)	−0.0012 (9)	−0.0018 (8)
C15	0.0274 (9)	0.0285 (10)	0.0282 (10)	−0.0032 (8)	−0.0076 (7)	0.0032 (8)
C16	0.0214 (7)	0.0187 (8)	0.0248 (9)	0.0011 (6)	−0.0009 (6)	0.0029 (7)

Cl1—C2	1.7288 (18)	C6—H6	0.9500
O1—C7	1.309 (2)	C8—C9	1.411 (3)
O1—H1	0.95 (4)	C8—H8	0.9500
O2—C7	1.208 (2)	C9—C10	1.361 (3)
O3—N1	1.228 (2)	C9—H9	0.9500
O4—N1	1.225 (2)	C10—C11	1.412 (3)
N1—C4	1.478 (2)	C10—H10	0.9500
N2—C8	1.315 (3)	C11—C12	1.416 (2)
N2—C16	1.368 (2)	C11—C16	1.424 (2)
C1—C2	1.398 (2)	C12—C13	1.356 (3)
C1—C6	1.402 (2)	C12—H12	0.9500
C1—C7	1.512 (2)	C13—C14	1.410 (3)
C2—C3	1.391 (2)	C13—H13	0.9500
C3—C4	1.383 (3)	C14—C15	1.366 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.382 (2)	C15—C16	1.412 (3)
C5—C6	1.386 (3)	C15—H15	0.9500
C5—H5	0.9500
C7—O1—H1	115 (2)	N2—C8—H8	118.4
O4—N1—O3	124.05 (16)	C9—C8—H8	118.4
O4—N1—C4	117.93 (16)	C10—C9—C8	118.72 (19)
O3—N1—C4	118.01 (17)	C10—C9—H9	120.6
C8—N2—C16	119.27 (16)	C8—C9—H9	120.6
C2—C1—C6	118.54 (16)	C9—C10—C11	120.10 (18)
C2—C1—C7	122.99 (16)	C9—C10—H10	119.9
C6—C1—C7	118.46 (15)	C11—C10—H10	119.9
C3—C2—C1	120.81 (16)	C10—C11—C12	123.67 (16)
C3—C2—Cl1	116.97 (13)	C10—C11—C16	117.62 (16)
C1—C2—Cl1	122.21 (13)	C12—C11—C16	118.71 (17)
C4—C3—C2	118.06 (16)	C13—C12—C11	120.40 (17)
C4—C3—H3	121.0	C13—C12—H12	119.8
C2—C3—H3	121.0	C11—C12—H12	119.8
C5—C4—C3	123.47 (16)	C12—C13—C14	120.93 (19)
C5—C4—N1	118.84 (16)	C12—C13—H13	119.5
C3—C4—N1	117.70 (16)	C14—C13—H13	119.5
C4—C5—C6	117.27 (16)	C15—C14—C13	120.44 (19)
C4—C5—H5	121.4	C15—C14—H14	119.8
C6—C5—H5	121.4	C13—C14—H14	119.8
C5—C6—C1	121.79 (16)	C14—C15—C16	120.04 (18)
C5—C6—H6	119.1	C14—C15—H15	120.0
C1—C6—H6	119.1	C16—C15—H15	120.0
O2—C7—O1	125.46 (17)	N2—C16—C15	119.44 (16)
O2—C7—C1	122.49 (17)	N2—C16—C11	121.08 (16)
O1—C7—C1	112.03 (15)	C15—C16—C11	119.48 (16)
N2—C8—C9	123.19 (18)
C6—C1—C2—C3	−0.6 (3)	C6—C1—C7—O1	−39.1 (2)
C7—C1—C2—C3	178.35 (17)	C16—N2—C8—C9	−0.6 (3)
C6—C1—C2—Cl1	178.32 (14)	N2—C8—C9—C10	−0.3 (3)
C7—C1—C2—Cl1	−2.7 (2)	C8—C9—C10—C11	1.1 (3)
C1—C2—C3—C4	−1.5 (3)	C9—C10—C11—C12	178.46 (18)
Cl1—C2—C3—C4	179.46 (13)	C9—C10—C11—C16	−1.1 (3)
C2—C3—C4—C5	2.1 (3)	C10—C11—C12—C13	−179.86 (18)
C2—C3—C4—N1	−178.12 (16)	C16—C11—C12—C13	−0.3 (3)
O4—N1—C4—C5	−12.2 (3)	C11—C12—C13—C14	−0.3 (3)
O3—N1—C4—C5	168.76 (18)	C12—C13—C14—C15	0.8 (3)
O4—N1—C4—C3	168.02 (18)	C13—C14—C15—C16	−0.7 (3)
O3—N1—C4—C3	−11.0 (3)	C8—N2—C16—C15	−179.17 (18)
C3—C4—C5—C6	−0.4 (3)	C8—N2—C16—C11	0.6 (3)
N1—C4—C5—C6	179.82 (17)	C14—C15—C16—N2	179.84 (18)
C4—C5—C6—C1	−1.9 (3)	C14—C15—C16—C11	0.1 (3)
C2—C1—C6—C5	2.4 (3)	C10—C11—C16—N2	0.2 (3)
C7—C1—C6—C5	−176.60 (18)	C12—C11—C16—N2	−179.33 (16)
C2—C1—C7—O2	−39.8 (3)	C10—C11—C16—C15	179.98 (17)
C6—C1—C7—O2	139.2 (2)	C12—C11—C16—C15	0.4 (3)
C2—C1—C7—O1	141.92 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.95 (3)	1.65 (3)	2.595 (2)	177 (3)
C5—H5···O2i	0.95	2.44	3.251 (2)	143
C9—H9···O4ii	0.95	2.57	3.365 (3)	141
C14—H14···O3i	0.95	2.55	3.476 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.95 (3)	1.65 (3)	2.595 (2)	177 (3)
C5—H5⋯O2i	0.95	2.44	3.251 (2)	143
C9—H9⋯O4ii	0.95	2.57	3.365 (3)	141
C14—H14⋯O3i	0.95	2.55	3.476 (3)	165

Symmetry codes: (i) ; (ii) .