Crystal structure of 3-[(2-acetyl­phen­oxy)carbon­yl]benzoic acid

Abstract

In the title compound, C₁₆H₁₂O₅, synthesized from isopthaloyl chloride and 2′-hy­droxy­aceto­phenone, the dihedral angle between the planes of the aromatic rings is 71.37 (9)°. In the crystal, carb­oxy­lic acid inversion dimers generate R ₂ ²(8) loops. The dimers are linked by C—H⋯O inter­actions, generating (101) sheets.

Related literature  

For related structures, see: Derissen (1974 ▶); Tanimoto et al. (1973 ▶).

Experimental  

Crystal data  

• C₁₆H₁₂O₅

• M _r = 284.26

• Monoclinic,

• a = 13.5081 (10) Å

• b = 7.4743 (6) Å

• c = 13.9421 (11) Å

• β = 106.671 (3)°

• V = 1348.48 (18) ų

• Z = 4

• Mo Kα radiation

• μ = 0.11 mm⁻¹

• T = 296 K

• 0.38 × 0.28 × 0.25 mm

Data collection  

• Bruker Kappa APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.963, T _max = 0.977

• 10280 measured reflections

• 2655 independent reflections

• 1971 reflections with I > 2σ(I)

• R _int = 0.022

Refinement  

• R[F ² > 2σ(F ²)] = 0.041

• wR(F ²) = 0.115

• S = 1.03

• 2655 reflections

• 192 parameters

• H-atom parameters constrained

• Δρ_max = 0.18 e Å⁻³

• Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Supplementary Material

CCDC reference: 1027627

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1H1O2i	0.82	1.84	2.6623(18)	175
C4H4O5ii	0.93	2.58	3.257(3)	130

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

S1. Comment

The title compound (I), (Fig. 1) has been synthesized for forming different metal complexes. The crystal structures of isophthalic acid and acetophenone have been published by (Derissen, 1974) and (Tanimoto, et al., 1973) which are related to the title compound (I).

In (I) the group A (C1—C8/O1—O4) being like a part of isophthalic acid and benzene ring attached to it B (C9—C13) are almost planar with r. m. s. deviation of 0.0308 and 0.0034 Å, respectively. The dihedral angle between A/B is 71.98 (5)°. The acetaldehyde group C (O5/C15/C16) attached to ring B is of course planar. The dihedral angle between B/C is 9.56 (23)°. The molecules are dimerized due to coventional H-bondings of O—H···O type (Table 1, Fig. 2) forming R₂²(8) loop. The dimers are further interlinked due to C—H···O bondings where C—H is of benzene containing carboxylate and O is of acetaldehyde group.

S2. Experimental

Isopthaloyl chloride (25 mmol) and 2'-hydroxyacetophenone (35 mmol) were refluxed in the aquauos solution of pyridine for 30 min. The mixture was cooled to room temperature and added to a beaker containing 2 N HCl. The crushed ice was added and stirred vigorously. The precipitate formed were obtained though filteration. The column chromatography was done ethyl acetate:n-hexane (4:6) to obtain the pure product. Light yellow prisms were obtained after two days.

S3. Refinement

All H atoms were geometrically placed [(O–H = 0.82 Å (hydroxyl), C–H = 0.93 Å (aromatic) and C–H = 0.96 Å (methyl) and refined as riding with with U_iso(H) = xU_eq(C, O), where x = 1.5 for hydroxy & methyl and x = 1.2 for aromatic H-atoms.

Figures

Fig. 1.

View of the title compound with displacement ellipsoids drawn at the 50% probability level.

Fig. 2.

The partial packing (PLATON; Spek, 2009), which shows that molecules form dimers which are interlinked.

Crystal data

C16H12O5	F(000) = 592
Mr = 284.26	Dx = 1.400 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.5081 (10) Å	Cell parameters from 1971 reflections
b = 7.4743 (6) Å	θ = 1.9–26.0°
c = 13.9421 (11) Å	µ = 0.11 mm−1
β = 106.671 (3)°	T = 296 K
V = 1348.48 (18) Å3	Prism, light yellow
Z = 4	0.38 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	2655 independent reflections
Radiation source: fine-focus sealed tube	1971 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 7.50 pixels mm-1	θmax = 26.0°, θmin = 1.9°
ω scans	h = −15→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→9
Tmin = 0.963, Tmax = 0.977	l = −17→17
10280 measured reflections

Refinement

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.4011P] where P = (Fo2 + 2Fc2)/3
2655 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 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
O1	0.36130 (10)	0.0311 (2)	0.47366 (9)	0.0704 (5)
H1	0.4166	0.0276	0.5177	0.106*
O2	0.46474 (9)	−0.0058 (2)	0.37694 (9)	0.0627 (4)
O3	0.14695 (9)	−0.0066 (2)	−0.05814 (9)	0.0669 (4)
O4	0.31564 (8)	−0.05274 (16)	0.01634 (7)	0.0411 (3)
O5	0.48190 (13)	0.2965 (2)	−0.11562 (12)	0.0767 (5)
C1	0.37753 (13)	0.0154 (2)	0.38694 (11)	0.0435 (4)
C2	0.28422 (12)	0.0221 (2)	0.29912 (11)	0.0370 (4)
C3	0.18668 (13)	0.0478 (2)	0.31086 (12)	0.0435 (4)
H3	0.1791	0.0628	0.3746	0.052*
C4	0.10086 (13)	0.0512 (3)	0.22840 (13)	0.0505 (5)
H4	0.0355	0.0673	0.2366	0.061*
C5	0.11211 (13)	0.0306 (3)	0.13359 (13)	0.0471 (4)
H5	0.0542	0.0336	0.0780	0.056*
C6	0.20966 (12)	0.0052 (2)	0.12066 (11)	0.0368 (4)
C7	0.29593 (12)	0.0005 (2)	0.20355 (11)	0.0370 (4)
H7	0.3613	−0.0169	0.1955	0.044*
C8	0.21703 (12)	−0.0183 (2)	0.01684 (12)	0.0404 (4)
C9	0.33430 (12)	−0.0900 (2)	−0.07617 (11)	0.0381 (4)
C10	0.30562 (14)	−0.2564 (3)	−0.11818 (13)	0.0485 (4)
H10	0.2692	−0.3350	−0.0892	0.058*
C11	0.33147 (15)	−0.3054 (3)	−0.20375 (13)	0.0560 (5)
H11	0.3132	−0.4178	−0.2319	0.067*
C12	0.38433 (14)	−0.1876 (3)	−0.24715 (13)	0.0552 (5)
H12	0.4012	−0.2199	−0.3049	0.066*
C13	0.41194 (13)	−0.0225 (3)	−0.20493 (12)	0.0476 (5)
H13	0.4474	0.0559	−0.2351	0.057*
C14	0.38845 (12)	0.0318 (2)	−0.11770 (11)	0.0375 (4)
C15	0.42394 (13)	0.2153 (2)	−0.07883 (12)	0.0456 (4)
C16	0.38994 (17)	0.3003 (3)	0.00334 (16)	0.0614 (5)
H16A	0.4174	0.4195	0.0148	0.092*
H16B	0.4148	0.2311	0.0635	0.092*
H16C	0.3158	0.3051	−0.0154	0.092*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0455 (8)	0.1379 (14)	0.0272 (6)	0.0069 (9)	0.0097 (5)	−0.0055 (7)
O2	0.0363 (7)	0.1189 (13)	0.0323 (6)	0.0023 (7)	0.0089 (5)	−0.0024 (7)
O3	0.0391 (7)	0.1245 (13)	0.0328 (7)	0.0139 (7)	0.0037 (5)	0.0015 (7)
O4	0.0325 (6)	0.0653 (8)	0.0264 (5)	−0.0005 (5)	0.0097 (4)	−0.0007 (5)
O5	0.0916 (11)	0.0748 (10)	0.0791 (10)	−0.0290 (9)	0.0495 (9)	−0.0073 (8)
C1	0.0401 (10)	0.0629 (12)	0.0286 (8)	−0.0013 (8)	0.0116 (7)	−0.0012 (7)
C2	0.0356 (9)	0.0454 (10)	0.0305 (8)	−0.0018 (7)	0.0104 (6)	0.0008 (6)
C3	0.0430 (10)	0.0594 (11)	0.0321 (8)	−0.0023 (8)	0.0169 (7)	−0.0031 (7)
C4	0.0338 (9)	0.0763 (13)	0.0449 (10)	0.0017 (9)	0.0171 (8)	−0.0054 (9)
C5	0.0329 (9)	0.0706 (13)	0.0360 (9)	0.0009 (8)	0.0071 (7)	−0.0027 (8)
C6	0.0324 (8)	0.0483 (10)	0.0300 (8)	−0.0011 (7)	0.0097 (6)	0.0008 (7)
C7	0.0313 (8)	0.0500 (10)	0.0312 (8)	−0.0018 (7)	0.0113 (6)	0.0011 (7)
C8	0.0317 (8)	0.0574 (11)	0.0311 (8)	0.0010 (7)	0.0074 (7)	0.0027 (7)
C9	0.0317 (8)	0.0567 (11)	0.0256 (7)	0.0028 (7)	0.0077 (6)	−0.0007 (7)
C10	0.0474 (10)	0.0557 (11)	0.0418 (9)	−0.0069 (9)	0.0118 (8)	−0.0027 (8)
C11	0.0544 (11)	0.0617 (13)	0.0480 (10)	−0.0025 (9)	0.0082 (9)	−0.0173 (9)
C12	0.0499 (11)	0.0804 (15)	0.0376 (9)	0.0033 (10)	0.0161 (8)	−0.0135 (9)
C13	0.0411 (9)	0.0692 (13)	0.0362 (9)	0.0021 (8)	0.0172 (7)	0.0005 (8)
C14	0.0296 (8)	0.0522 (10)	0.0307 (8)	0.0036 (7)	0.0087 (6)	0.0012 (7)
C15	0.0404 (9)	0.0555 (11)	0.0419 (9)	−0.0006 (8)	0.0135 (8)	0.0047 (8)
C16	0.0714 (14)	0.0531 (12)	0.0682 (13)	−0.0077 (10)	0.0335 (11)	−0.0133 (10)

Geometric parameters (Å, º)

O1—C1	1.2946 (19)	C6—C8	1.489 (2)
O1—H1	0.8200	C7—H7	0.9300
O2—C1	1.236 (2)	C9—C10	1.382 (2)
O3—C8	1.1953 (19)	C9—C14	1.394 (2)
O4—C8	1.3587 (19)	C10—C11	1.385 (2)
O4—C9	1.4111 (17)	C10—H10	0.9300
O5—C15	1.215 (2)	C11—C12	1.379 (3)
C1—C2	1.485 (2)	C11—H11	0.9300
C2—C3	1.387 (2)	C12—C13	1.372 (3)
C2—C7	1.395 (2)	C12—H12	0.9300
C3—C4	1.379 (2)	C13—C14	1.402 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.382 (2)	C14—C15	1.502 (2)
C4—H4	0.9300	C15—C16	1.493 (2)
C5—C6	1.393 (2)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.386 (2)	C16—H16C	0.9600
C1—O1—H1	109.5	C10—C9—O4	117.60 (14)
C8—O4—C9	118.33 (12)	C14—C9—O4	120.23 (15)
O2—C1—O1	122.65 (15)	C9—C10—C11	119.60 (17)
O2—C1—C2	121.50 (14)	C9—C10—H10	120.2
O1—C1—C2	115.84 (14)	C11—C10—H10	120.2
C3—C2—C7	120.03 (15)	C12—C11—C10	119.96 (18)
C3—C2—C1	121.19 (14)	C12—C11—H11	120.0
C7—C2—C1	118.78 (14)	C10—C11—H11	120.0
C4—C3—C2	120.27 (15)	C13—C12—C11	119.85 (16)
C4—C3—H3	119.9	C13—C12—H12	120.1
C2—C3—H3	119.9	C11—C12—H12	120.1
C3—C4—C5	119.91 (15)	C12—C13—C14	122.08 (17)
C3—C4—H4	120.0	C12—C13—H13	119.0
C5—C4—H4	120.0	C14—C13—H13	119.0
C4—C5—C6	120.44 (15)	C9—C14—C13	116.61 (16)
C4—C5—H5	119.8	C9—C14—C15	126.71 (14)
C6—C5—H5	119.8	C13—C14—C15	116.68 (15)
C7—C6—C5	119.71 (14)	O5—C15—C16	119.23 (18)
C7—C6—C8	122.18 (14)	O5—C15—C14	118.82 (16)
C5—C6—C8	118.11 (14)	C16—C15—C14	121.95 (15)
C6—C7—C2	119.65 (15)	C15—C16—H16A	109.5
C6—C7—H7	120.2	C15—C16—H16B	109.5
C2—C7—H7	120.2	H16A—C16—H16B	109.5
O3—C8—O4	122.75 (15)	C15—C16—H16C	109.5
O3—C8—C6	125.75 (15)	H16A—C16—H16C	109.5
O4—C8—C6	111.49 (13)	H16B—C16—H16C	109.5
C10—C9—C14	121.90 (14)
O2—C1—C2—C3	−179.32 (18)	C5—C6—C8—O4	−176.17 (15)
O1—C1—C2—C3	1.4 (3)	C8—O4—C9—C10	−74.90 (19)
O2—C1—C2—C7	1.2 (3)	C8—O4—C9—C14	110.95 (17)
O1—C1—C2—C7	−178.08 (17)	C14—C9—C10—C11	0.3 (3)
C7—C2—C3—C4	0.4 (3)	O4—C9—C10—C11	−173.72 (15)
C1—C2—C3—C4	−179.14 (17)	C9—C10—C11—C12	−0.8 (3)
C2—C3—C4—C5	−0.6 (3)	C10—C11—C12—C13	0.5 (3)
C3—C4—C5—C6	0.4 (3)	C11—C12—C13—C14	0.2 (3)
C4—C5—C6—C7	0.0 (3)	C10—C9—C14—C13	0.4 (2)
C4—C5—C6—C8	179.31 (17)	O4—C9—C14—C13	174.31 (13)
C5—C6—C7—C2	−0.3 (3)	C10—C9—C14—C15	−179.79 (16)
C8—C6—C7—C2	−179.53 (15)	O4—C9—C14—C15	−5.9 (2)
C3—C2—C7—C6	0.1 (2)	C12—C13—C14—C9	−0.7 (2)
C1—C2—C7—C6	179.60 (15)	C12—C13—C14—C15	179.48 (16)
C9—O4—C8—O3	−5.1 (3)	C9—C14—C15—O5	170.50 (17)
C9—O4—C8—C6	175.91 (14)	C13—C14—C15—O5	−9.7 (2)
C7—C6—C8—O3	−175.87 (18)	C9—C14—C15—C16	−9.6 (3)
C5—C6—C8—O3	4.9 (3)	C13—C14—C15—C16	170.19 (17)
C7—C6—C8—O4	3.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.84	2.6623 (18)	175
C4—H4···O5ii	0.93	2.58	3.257 (3)	130

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