2-(2-Methoxy­phenyl­sulfan­yl)benzoic acid

The title compound, C₁₄H₁₂O₃S, was synthesized from 2-methoxy­thio­phenol and 2-chloro­benzoic acid with copper powder as catalyst. In the mol­ecule, the two benzene ring planes are roughly perpendicular. The mol­ecules are linked through an inversion center by O—H...O hydrogen bonds, forming a pseudo-dimer.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.162
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.85
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

2-(2-methoxyphenylsulfanyl)benzoic acid

Crystal data

C14H12O3S	Z = 2
Mr = 260.30	F(000) = 272
Triclinic, P1	Dx = 1.413 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.165 (3) Å	Cell parameters from 1160 reflections
b = 7.768 (3) Å	θ = 2.9–26.0°
c = 11.907 (4) Å	µ = 0.26 mm^−1
α = 103.505 (6)°	T = 294 K
β = 100.886 (6)°	Block, colourless
γ = 101.474 (6)°	0.32 × 0.30 × 0.24 mm
V = 612.0 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2131 independent reflections
Radiation source: fine-focus sealed tube	1578 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→8
Tmin = 0.920, Tmax = 0.939	k = −9→8
3112 measured reflections	l = −14→12

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.104P)^2] where P = (Fo^2 + 2Fc^2)/3
2131 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −0.23 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
S1	0.38059 (11)	0.84065 (10)	0.28674 (7)	0.0405 (3)
O1	0.9762 (3)	1.2007 (3)	0.4553 (2)	0.0549 (7)
H1	1.0497	1.1552	0.4939	0.082*
O2	0.7597 (3)	0.9411 (3)	0.43516 (19)	0.0457 (6)
O3	0.2960 (3)	0.8358 (4)	0.0329 (2)	0.0573 (7)
C1	0.7966 (4)	1.0962 (4)	0.4247 (2)	0.0353 (7)
C2	0.6456 (4)	1.1831 (4)	0.3790 (2)	0.0336 (7)
C3	0.6957 (5)	1.3732 (4)	0.4007 (3)	0.0419 (8)
H3	0.8245	1.4390	0.4390	0.050*
C4	0.5605 (5)	1.4653 (4)	0.3672 (3)	0.0478 (9)
H4	0.5968	1.5919	0.3826	0.057*
C5	0.3699 (5)	1.3676 (4)	0.3102 (3)	0.0458 (8)
H5	0.2762	1.4286	0.2877	0.055*
C6	0.3179 (5)	1.1802 (4)	0.2866 (3)	0.0398 (7)
H6	0.1888	1.1165	0.2474	0.048*
C7	0.4511 (4)	1.0837 (4)	0.3192 (2)	0.0321 (7)
C8	0.1477 (4)	0.7824 (4)	0.1845 (3)	0.0343 (7)
C9	−0.0198 (5)	0.7292 (5)	0.2224 (3)	0.0473 (8)
H9	−0.0082	0.7300	0.3017	0.057*
C10	−0.2038 (5)	0.6750 (6)	0.1453 (4)	0.0625 (10)
H10	−0.3155	0.6401	0.1720	0.075*
C11	−0.2194 (5)	0.6734 (5)	0.0293 (4)	0.0630 (11)
H11	−0.3429	0.6360	−0.0236	0.076*
C12	−0.0570 (5)	0.7259 (5)	−0.0105 (3)	0.0534 (9)
H12	−0.0712	0.7251	−0.0899	0.064*
C13	0.1287 (4)	0.7804 (4)	0.0654 (3)	0.0392 (7)
C14	0.2810 (7)	0.8322 (6)	−0.0890 (3)	0.0724 (12)
H14A	0.2189	0.7100	−0.1391	0.109*
H14B	0.4100	0.8707	−0.1007	0.109*
H14C	0.2038	0.9135	−0.1092	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0352 (5)	0.0328 (5)	0.0440 (5)	0.0059 (3)	−0.0069 (3)	0.0084 (3)
O1	0.0278 (12)	0.0501 (14)	0.0820 (18)	0.0043 (10)	−0.0036 (11)	0.0276 (12)
O2	0.0338 (11)	0.0388 (13)	0.0552 (14)	0.0085 (10)	−0.0079 (10)	0.0113 (10)
O3	0.0431 (13)	0.0774 (18)	0.0416 (13)	−0.0053 (12)	0.0098 (10)	0.0160 (12)
C1	0.0304 (16)	0.0372 (18)	0.0298 (15)	0.0038 (13)	−0.0022 (12)	0.0053 (13)
C2	0.0331 (15)	0.0370 (16)	0.0276 (14)	0.0075 (13)	0.0017 (12)	0.0089 (12)
C3	0.0359 (16)	0.0389 (17)	0.0421 (17)	0.0025 (13)	−0.0014 (13)	0.0093 (14)
C4	0.053 (2)	0.0303 (16)	0.050 (2)	0.0078 (15)	−0.0065 (16)	0.0087 (14)
C5	0.0429 (18)	0.0429 (19)	0.0445 (19)	0.0155 (15)	−0.0069 (15)	0.0091 (15)
C6	0.0355 (16)	0.0412 (18)	0.0354 (16)	0.0109 (13)	−0.0056 (13)	0.0074 (13)
C7	0.0359 (16)	0.0329 (15)	0.0264 (14)	0.0081 (12)	0.0058 (12)	0.0084 (12)
C8	0.0310 (15)	0.0295 (15)	0.0347 (16)	0.0055 (12)	0.0000 (12)	0.0032 (12)
C9	0.0403 (18)	0.052 (2)	0.0449 (19)	0.0054 (15)	0.0111 (15)	0.0102 (15)
C10	0.0338 (19)	0.068 (3)	0.082 (3)	0.0052 (17)	0.0184 (18)	0.017 (2)
C11	0.0327 (19)	0.065 (3)	0.072 (3)	0.0005 (17)	−0.0086 (18)	0.010 (2)
C12	0.047 (2)	0.055 (2)	0.0452 (19)	0.0022 (16)	−0.0081 (16)	0.0143 (16)
C13	0.0352 (16)	0.0338 (16)	0.0413 (17)	0.0019 (13)	0.0020 (13)	0.0086 (13)
C14	0.085 (3)	0.077 (3)	0.049 (2)	−0.002 (2)	0.021 (2)	0.021 (2)

Geometric parameters (Å, º)

S1—C8	1.774 (3)	C6—C7	1.380 (4)
S1—C7	1.782 (3)	C6—H6	0.9300
O1—C1	1.311 (3)	C8—C9	1.382 (4)
O1—H1	0.8200	C8—C13	1.394 (4)
O2—C1	1.222 (3)	C9—C10	1.379 (5)
O3—C13	1.349 (4)	C9—H9	0.9300
O3—C14	1.429 (4)	C10—C11	1.361 (6)
C1—C2	1.470 (4)	C10—H10	0.9300
C2—C3	1.398 (4)	C11—C12	1.362 (5)
C2—C7	1.409 (4)	C11—H11	0.9300
C3—C4	1.368 (4)	C12—C13	1.382 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.378 (4)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.375 (4)	C14—H14C	0.9600
C5—H5	0.9300
C8—S1—C7	102.44 (13)	C9—C8—C13	118.9 (3)
C1—O1—H1	109.5	C9—C8—S1	119.1 (2)
C13—O3—C14	117.9 (3)	C13—C8—S1	122.0 (2)
O2—C1—O1	122.3 (3)	C10—C9—C8	121.4 (3)
O2—C1—C2	123.6 (3)	C10—C9—H9	119.3
O1—C1—C2	114.2 (3)	C8—C9—H9	119.3
C3—C2—C7	118.9 (3)	C11—C10—C9	118.9 (3)
C3—C2—C1	118.3 (3)	C11—C10—H10	120.5
C7—C2—C1	122.7 (3)	C9—C10—H10	120.5
C4—C3—C2	121.8 (3)	C10—C11—C12	121.0 (3)
C4—C3—H3	119.1	C10—C11—H11	119.5
C2—C3—H3	119.1	C12—C11—H11	119.5
C3—C4—C5	119.0 (3)	C11—C12—C13	120.9 (3)
C3—C4—H4	120.5	C11—C12—H12	119.5
C5—C4—H4	120.5	C13—C12—H12	119.5
C6—C5—C4	120.2 (3)	O3—C13—C12	124.3 (3)
C6—C5—H5	119.9	O3—C13—C8	116.7 (3)
C4—C5—H5	119.9	C12—C13—C8	118.9 (3)
C5—C6—C7	122.1 (3)	O3—C14—H14A	109.5
C5—C6—H6	119.0	O3—C14—H14B	109.5
C7—C6—H6	119.0	H14A—C14—H14B	109.5
C6—C7—C2	118.0 (3)	O3—C14—H14C	109.5
C6—C7—S1	121.3 (2)	H14A—C14—H14C	109.5
C2—C7—S1	120.7 (2)	H14B—C14—H14C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.85	2.658 (3)	171

Symmetry code: (i) −x+2, −y+2, −z+1.