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

Shoaib, M.; Shah, I.; Shah, S.W.A.; Tahir, M.N.; Ullah, S.; Ayaz, M.

doi:10.1107/S1600536814021904

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Page o1153

doi:10.1107/S1600536814021904

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

Mohammad Shoaib,^a Ismail Shah,^a Syed Wadood Ali Shah,^a Muhammad Nawaz Tahir,^b ^* Shafi Ullah ^a and Muhammad Ayaz ^a

^aDepartment of Pharmacy, University of Malakand, Khyber Pakhtunkhwa, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 4 October 2014; accepted 4 October 2014; online 11 October 2014)

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 R₂²(8) loops. The dimers are linked by C—H⋯O interactions, generating (101) sheets.

Keywords: crystal structure; 3-[(2-acetylphenoxy)carbonyl]benzoic acid; hydrogen bonding; 2′-hydroxyacetophenone; isopthaloyl chloride.

CCDC reference: 1027627

1. Related literature

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

2. Experimental

2.1. Crystal data

C₁₆H₁₂O₅
M_r = 284.26
Monoclinic, P 2₁ /n
a = 13.5081 (10) Å
b = 7.4743 (6) Å
c = 13.9421 (11) Å
β = 106.671 (3)°
V = 1348.48 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.38 × 0.28 × 0.25 mm

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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

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.

Supporting information

CCDC reference: 1027627

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814021904/hb7293sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814021904/hb7293Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814021904/hb7293Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

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.

3-[(2-Acetylphenoxy)carbonyl]benzoic acid top

Crystal data top

C₁₆H₁₂O₅	F(000) = 592
M_r = 284.26	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0505P)² + 0.4011P] where P = (F_o² + 2F_c²)/3
2655 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₆H₁₂O₅	V = 1348.48 (18) Å³
M_r = 284.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.5081 (10) Å	µ = 0.11 mm⁻¹
b = 7.4743 (6) Å	T = 296 K
c = 13.9421 (11) Å	0.38 × 0.28 × 0.25 mm
β = 106.671 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2655 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1971 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.977	R_int = 0.022
10280 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
2655 reflections	Δρ_min = −0.20 e Å⁻³
192 parameters

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
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 (Å²) top

	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) top

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) top

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.

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

The authors are grateful to the University of Malakand, Khyber Pakhtunkhwa, Pakistan, for provision of laboratory facilities for carrying out this research work.

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