2-Chloro-4-nitro­benzoic acid–quinoline (1/1)

Gotoh, K.; Ishida, H.

doi:10.1107/S160053681104075X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2883

doi:10.1107/S160053681104075X

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2-Chloro-4-nitrobenzoic acid–quinoline (1/1)

Kazuma Gotoh ^a and Hiroyuki Ishida ^a ^*

^aDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
^*Correspondence e-mail: ishidah@cc.okayama-u.ac.jp

(Received 28 September 2011; accepted 4 October 2011; online 8 October 2011)

In the title compound, C₇H₄ClNO₄·C₉H₇N, 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 intermolecular 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_r = 330.73
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.083
S = 1.06
4166 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1989 Friedel pairs
Flack parameter: 0.01 (5)

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) $[-x+1, -y+2, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681104075X/lh5345sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681104075X/lh5345Isup3.cml

checkCIF report

Comment top

The title compound was prepared in order to extend our study on D—H···A hydrogen bonding (D = N, O, or C; A = N, O or Cl) in quinoline–substituted benzoic acid systems (Gotoh & Ishida, 2009; Gotoh et al., 2010).

In the crystal structure of the title compound, no acid-base interaction involving proton transfer is observed between the two components, which are linked by an O—H···N hydrogen bond (Table 1 and Fig. 1). In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of the benzoic acid is 3.15 (7)°. The carboxyl plane makes dihedral angles of 43.0 (2) and 39.9 (2)°, respectively, with the quinoline ring system and the benzene ring. The two components are further linked by intermolecular C—H···O hydrogen bonds (Table 1), forming a tape along the c axis and the tapes are stacked along the b axis through an C—H···O hydrogen bond into a layer parallel to the bc plane (Fig. 2). No significant interaction is observed between the layers.

Related literature top

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

Experimental top

Single crystals were obtained by slow evaporation from an acetonitrile solution (30 ml) of 2-chloro-4-nitrobenzoic acid (233 mg) and quinoline (150 mg) at room temperature.

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2004); 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).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level. The dashed line indicates the O—H···N hydrogen bond.
	Fig. 2. A partial packing diagram of the title compound viewed along the b axis, showing a layer parallel to the bc plane formed by O—H···N and C—H···O hydrogen bonds (dashed lines). [Symmetry codes: (i) -x + 1, -y + 2, z + 1/2; (iii) -x + 1, -y + 2, z - 1/2.]

2-Chloro-4-nitrobenzoic acid–quinoline (1/1) top

Crystal data top

C₉H₇N·C₇H₄ClNO₄	F(000) = 680.00
M_r = 330.73	D_x = 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

Data collection top

Rigaku R-AXIS RAPID II diffractometer	3681 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.053
ω scans	θ_max = 29.9°, θ_min = 3.1°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −42→43
T_min = 0.925, T_max = 0.983	k = −4→5
17044 measured reflections	l = −17→17
4166 independent reflections

Refinement top

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(F_o²) + (0.0315P)² + 0.3405P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.002
4166 reflections	Δρ_max = 0.23 e Å⁻³
212 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1989 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

Crystal data top

C₉H₇N·C₇H₄ClNO₄	V = 1445.1 (2) Å³
M_r = 330.73	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 31.125 (3) Å	µ = 0.29 mm⁻¹
b = 3.7560 (3) Å	T = 185 K
c = 12.3615 (12) Å	0.35 × 0.22 × 0.06 mm

Data collection top

Rigaku R-AXIS RAPID II diffractometer	4166 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	3681 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.983	R_int = 0.053
17044 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.083	Δρ_max = 0.23 e Å⁻³
S = 1.06	Δρ_min = −0.25 e Å⁻³
4166 reflections	Absolute structure: Flack (1983), 1989 Friedel pairs
212 parameters	Absolute structure parameter: 0.01 (5)
1 restraint

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, z+1/2; (ii) −x+1, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₉H₇N·C₇H₄ClNO₄
M_r	330.73
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	185
a, b, c (Å)	31.125 (3), 3.7560 (3), 12.3615 (12)
V (Å³)	1445.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.35 × 0.22 × 0.06

Data collection
Diffractometer	Rigaku R-AXIS RAPID II diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.925, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	17044, 4166, 3681
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.083, 1.06
No. of reflections	4166
No. of parameters	212
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.25
Absolute structure	Flack (1983), 1989 Friedel pairs
Absolute structure parameter	0.01 (5)

Computer programs: PROCESS-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, z+1/2; (ii) −x+1, −y+1, z−1/2.

Acknowledgements

This work was supported by a Grant-in-Aid for Scientific Research (C) (No. 22550013) from the Japan Society for the Promotion of Science.

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