2-(4-Chloro­benzo­yl)benzoic acid

Crystals of the title compound, C₁₄H₉ClO₃, are stabilized by O—H...O and C—H...O hydrogen bonds and C—H...π inter­actions. O—H...O hydrogen bonds generate centrosymmetric dimers. O—H...O and two C—H...O hydrogen bonds generate spiro­cyclic R₂²(8)R₂¹(5) ring motifs. The R₂²(8) and R₂¹(5) ring motifs are connected to each other by C(6) chains and C—H...π inter­actions. The dihedral angle between the aromatic rings is 88.07 (11)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.110
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.72 mm
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit     -P 2yc
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  O1      ..       2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  O1      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O3      ..       2.83 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 5 Informative message, check

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S1. Comment

The present work is part of a structural study of carbonyl compounds (Odabaşoğlu & Büyükgüngör, 2006) and we report here the structure of 3-(4-ethoxyanilino)isobenzofuran-1(3H)-one, (I), Fig. 1, Table 1. The dihedral angle between aromatic rings is 88.07 (11)°. The bond lengths and angles are in normal ranges, and comparable with in our previous work on carbonyl compounds (Büyükgüngör & Odabaşoğlu, 2006; Odabaşoğlu & Büyükgüngör, 2006; Odabaşoğlu et al., 2006; Odabaşoğlu et al., 2005; Ersanlı et al., 2005; Allen et al., 1987). The C2—O1 bond distance in (I) is also consistent with the value of the C=O double bond in carbonyl compounds (Loudon, 2002).

The title compound, I, are stabilized by one O—H···O, three C—H···O intermolecular hydrogen bonds and one C—H···π interactions. O—H···O hydrogen bonds generate centrocymmetric dimers. O—H···O and two C—H···O hydrogenbonds generate spirocyclic R₂²(8)R₂¹(5) ring motifs (Etter, 1990) these motifs are connected by C(6) chains and C—H···π interactions (Fig. 2 and 3).

Related literature

For related structures, see: Allen et al. (1987); Odabaşoğlu et al. (2005); Büyükgüngör & Odabaşoğlu (2006); Odabaşoğlu & Büyükgüngör (2006); Odabaşoğlu et al. (2006); Ersanlı et al. (2005); Etter (1990); Loudon (2002); Sheldrick (1990).

S2. Experimental

A pure sample of the compound was obtained from Alfa Aeser GmbH & Co KG, Germany, and crystallized by slow evaporation of a solution in ethyl DMF-H₂O (1:1 v/v) solution at room temperature, m.p. 425–425 K.

S3. Refinement

H atoms were placed in idealized positions with d(C—H) = 0.93 for aromatic, d(C—H) = 0.98 Å for methine and d(C—O)=0.82 Å for hydroxy and thereafter treated as riding. U_iso for H was assigned as 1.2 times U_eq of the attached C atoms (1.5 for O)

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. A view of (I) showing the atomic numbering scheme with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The R2^2(8)R2^1(5) ring motifs and π···π interactions of (I), with C For the sake of clarity, H atoms not involved in the hydrogen bonding motifs shown have been omitted; hydrogen bonds are drawn as dashed lines. [Symmetry codes: (i) -x, 1 - y, 1 - z; (ii) x - 1/2, y, z + 1/2].
	Fig. 3. The C(6) chain and R2^1(5) ring of (I),, with C For the sake of clarity, H atoms not involved in the hydrogen bonding motifs shown have been omitted; hydrogen bonds are drawn as dashed lines. [Symmetry codes: (i) x, 1/2 - y, z - 1/2; (ii) x, 1/2 - y, z + 1/2; (iii) -x, 1 - y, 1 - z].

2-(4-Chlorobenzoyl)benzoic acid

Crystal data

C14H9ClO3	F(000) = 536
Mr = 260.66	Dx = 1.394 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 6666 reflections
a = 15.3209 (17) Å	θ = 2.1–27.9°
b = 7.3171 (6) Å	µ = 0.30 mm^−1
c = 11.1988 (14) Å	T = 296 K
β = 98.467 (10)°	Prism, colorless
V = 1241.8 (2) Å^3	0.72 × 0.44 × 0.27 mm
Z = 4

Data collection

Stoe IPDSII diffractometer	2381 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1611 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.030
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 3.1°
ω scans	h = −18→15
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.839, Tmax = 0.919	l = −13→13
6666 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 0.074P] where P = (Fo^2 + 2Fc^2)/3
2381 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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	0.17454 (12)	0.0458 (2)	0.56843 (15)	0.0466 (4)
C2	0.10791 (12)	0.0997 (2)	0.47700 (15)	0.0438 (4)
C3	0.08082 (13)	−0.0174 (2)	0.38059 (16)	0.0520 (5)
H3	0.0357	0.0182	0.3202	0.062*
C4	0.12036 (14)	−0.1853 (3)	0.37402 (19)	0.0585 (5)
H4	0.1027	−0.2619	0.3086	0.070*
C5	0.18558 (16)	−0.2393 (2)	0.46361 (19)	0.0627 (6)
H5	0.2119	−0.3532	0.4595	0.075*
C6	0.21235 (14)	−0.1254 (2)	0.55999 (18)	0.0593 (5)
H6	0.2566	−0.1639	0.6206	0.071*
C7	0.06322 (12)	0.2779 (2)	0.48544 (15)	0.0449 (4)
C8	0.20686 (13)	0.1576 (2)	0.67855 (16)	0.0518 (5)
C9	0.27299 (12)	0.3042 (2)	0.67000 (16)	0.0509 (5)
C10	0.31668 (15)	0.3224 (3)	0.5719 (2)	0.0702 (6)
H10	0.3037	0.2425	0.5071	0.084*
C11	0.37936 (17)	0.4568 (4)	0.5675 (3)	0.0861 (8)
H11	0.4089	0.4672	0.5009	0.103*
C12	0.39722 (16)	0.5748 (3)	0.6631 (3)	0.0802 (7)
C13	0.35424 (16)	0.5614 (3)	0.7606 (2)	0.0742 (7)
H13	0.3668	0.6430	0.8245	0.089*
C14	0.29228 (15)	0.4270 (3)	0.76445 (18)	0.0624 (6)
H14	0.2629	0.4182	0.8312	0.075*
O1	0.00022 (9)	0.31239 (18)	0.39744 (11)	0.0607 (4)
H1	−0.0213	0.4126	0.4081	0.091*
O2	0.08373 (9)	0.38031 (16)	0.57144 (11)	0.0551 (4)
O3	0.18427 (12)	0.1185 (2)	0.77436 (12)	0.0769 (5)
Cl1	0.47438 (7)	0.74585 (13)	0.65780 (11)	0.1428 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0519 (11)	0.0417 (9)	0.0464 (9)	0.0039 (8)	0.0078 (8)	0.0043 (7)
C2	0.0461 (10)	0.0415 (8)	0.0445 (9)	0.0030 (7)	0.0087 (8)	0.0046 (7)
C3	0.0540 (12)	0.0511 (10)	0.0504 (10)	0.0019 (8)	0.0059 (8)	0.0005 (8)
C4	0.0668 (14)	0.0475 (10)	0.0611 (12)	−0.0015 (9)	0.0089 (10)	−0.0075 (9)
C5	0.0741 (15)	0.0390 (9)	0.0757 (14)	0.0078 (9)	0.0126 (11)	−0.0009 (9)
C6	0.0658 (14)	0.0473 (10)	0.0624 (12)	0.0133 (9)	0.0008 (10)	0.0096 (9)
C7	0.0468 (11)	0.0457 (9)	0.0424 (9)	0.0042 (7)	0.0074 (7)	0.0054 (8)
C8	0.0603 (13)	0.0490 (10)	0.0446 (10)	0.0136 (8)	0.0027 (9)	0.0060 (8)
C9	0.0491 (11)	0.0557 (10)	0.0443 (10)	0.0116 (8)	−0.0055 (8)	−0.0032 (8)
C10	0.0603 (14)	0.0828 (15)	0.0676 (13)	−0.0109 (12)	0.0097 (10)	−0.0228 (11)
C11	0.0650 (16)	0.0989 (18)	0.0979 (18)	−0.0186 (14)	0.0237 (13)	−0.0207 (15)
C12	0.0492 (14)	0.0755 (15)	0.112 (2)	−0.0041 (11)	−0.0013 (13)	−0.0195 (14)
C13	0.0692 (16)	0.0642 (13)	0.0816 (15)	0.0087 (11)	−0.0145 (12)	−0.0217 (11)
C14	0.0726 (15)	0.0596 (12)	0.0510 (11)	0.0146 (10)	−0.0039 (10)	−0.0042 (9)
O1	0.0658 (10)	0.0594 (7)	0.0523 (8)	0.0217 (7)	−0.0062 (6)	−0.0014 (6)
O2	0.0574 (9)	0.0466 (7)	0.0574 (8)	0.0108 (6)	−0.0048 (6)	−0.0061 (6)
O3	0.1141 (14)	0.0690 (9)	0.0496 (8)	0.0006 (8)	0.0187 (8)	0.0079 (7)
Cl1	0.0970 (7)	0.1214 (7)	0.2131 (11)	−0.0513 (5)	0.0328 (7)	−0.0505 (7)

Geometric parameters (Å, º)

C1—C6	1.389 (3)	C8—O3	1.209 (2)
C1—C2	1.392 (2)	C8—C9	1.488 (3)
C1—C8	1.502 (2)	C9—C10	1.375 (3)
C2—C3	1.393 (2)	C9—C14	1.386 (3)
C2—C7	1.483 (2)	C10—C11	1.381 (3)
C3—C4	1.377 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.371 (3)
C4—C5	1.366 (3)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.359 (4)
C5—C6	1.378 (3)	C12—Cl1	1.729 (3)
C5—H5	0.9300	C13—C14	1.372 (3)
C6—H6	0.9300	C13—H13	0.9300
C7—O2	1.224 (2)	C14—H14	0.9300
C7—O1	1.299 (2)	O1—H1	0.8200
C6—C1—C2	118.24 (16)	O3—C8—C1	119.80 (18)
C6—C1—C8	117.17 (16)	C9—C8—C1	119.02 (16)
C2—C1—C8	124.56 (15)	C10—C9—C14	118.2 (2)
C1—C2—C3	119.93 (16)	C10—C9—C8	122.50 (17)
C1—C2—C7	119.84 (15)	C14—C9—C8	119.27 (18)
C3—C2—C7	120.17 (16)	C9—C10—C11	121.4 (2)
C4—C3—C2	120.46 (18)	C9—C10—H10	119.3
C4—C3—H3	119.8	C11—C10—H10	119.3
C2—C3—H3	119.8	C12—C11—C10	118.7 (2)
C5—C4—C3	119.95 (18)	C12—C11—H11	120.6
C5—C4—H4	120.0	C10—C11—H11	120.6
C3—C4—H4	120.0	C13—C12—C11	121.2 (2)
C4—C5—C6	120.09 (17)	C13—C12—Cl1	119.6 (2)
C4—C5—H5	120.0	C11—C12—Cl1	119.2 (2)
C6—C5—H5	120.0	C12—C13—C14	119.8 (2)
C5—C6—C1	121.33 (18)	C12—C13—H13	120.1
C5—C6—H6	119.3	C14—C13—H13	120.1
C1—C6—H6	119.3	C13—C14—C9	120.8 (2)
O2—C7—O1	123.66 (15)	C13—C14—H14	119.6
O2—C7—C2	121.41 (15)	C9—C14—H14	119.6
O1—C7—C2	114.90 (15)	C7—O1—H1	109.5
O3—C8—C9	120.93 (17)
C6—C1—C2—C3	0.1 (3)	C6—C1—C8—C9	99.6 (2)
C8—C1—C2—C3	−177.79 (17)	C2—C1—C8—C9	−82.5 (2)
C6—C1—C2—C7	177.32 (17)	O3—C8—C9—C10	163.2 (2)
C8—C1—C2—C7	−0.6 (3)	C1—C8—C9—C10	−11.0 (3)
C1—C2—C3—C4	−0.9 (3)	O3—C8—C9—C14	−16.3 (3)
C7—C2—C3—C4	−178.14 (17)	C1—C8—C9—C14	169.48 (16)
C2—C3—C4—C5	1.2 (3)	C14—C9—C10—C11	1.1 (3)
C3—C4—C5—C6	−0.6 (3)	C8—C9—C10—C11	−178.4 (2)
C4—C5—C6—C1	−0.3 (3)	C9—C10—C11—C12	−0.6 (4)
C2—C1—C6—C5	0.5 (3)	C10—C11—C12—C13	−0.2 (4)
C8—C1—C6—C5	178.56 (19)	C10—C11—C12—Cl1	−179.1 (2)
C1—C2—C7—O2	0.2 (3)	C11—C12—C13—C14	0.5 (4)
C3—C2—C7—O2	177.39 (18)	Cl1—C12—C13—C14	179.28 (17)
C1—C2—C7—O1	−177.92 (16)	C12—C13—C14—C9	0.1 (3)
C3—C2—C7—O1	−0.7 (2)	C10—C9—C14—C13	−0.9 (3)
C6—C1—C8—O3	−74.7 (2)	C8—C9—C14—C13	178.60 (18)
C2—C1—C8—O3	103.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.82	2.6389 (17)	172
C3—H3···O1^ii	0.93	2.85	3.413 (2)	120
C4—H4···O1^ii	0.93	2.65	3.317 (2)	129
C5—H5···O3^iii	0.93	2.83	3.489 (2)	129
C14—H14···Cg^iii	0.93	2.77	3.592 (2)	149

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x, −y−1/2, z−1/2.