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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006428/dn6302sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006428/dn6302Isup2.hkl
Contains datablock I

CCDC reference: 601157

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

Computing details top

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 top
Crystal data top
C14H12O3SZ = 2
Mr = 260.30F(000) = 272
Triclinic, P1Dx = 1.413 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.165 (3) ÅCell parameters from 1160 reflections
b = 7.768 (3) Åθ = 2.9–26.0°
c = 11.907 (4) ŵ = 0.26 mm1
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) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2131 independent reflections
Radiation source: fine-focus sealed tube1578 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 88
Tmin = 0.920, Tmax = 0.939k = 98
3112 measured reflectionsl = 1412
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.104P)2]
where P = (Fo2 + 2Fc2)/3
2131 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
S10.38059 (11)0.84065 (10)0.28674 (7)0.0405 (3)
O10.9762 (3)1.2007 (3)0.4553 (2)0.0549 (7)
H11.04971.15520.49390.082*
O20.7597 (3)0.9411 (3)0.43516 (19)0.0457 (6)
O30.2960 (3)0.8358 (4)0.0329 (2)0.0573 (7)
C10.7966 (4)1.0962 (4)0.4247 (2)0.0353 (7)
C20.6456 (4)1.1831 (4)0.3790 (2)0.0336 (7)
C30.6957 (5)1.3732 (4)0.4007 (3)0.0419 (8)
H30.82451.43900.43900.050*
C40.5605 (5)1.4653 (4)0.3672 (3)0.0478 (9)
H40.59681.59190.38260.057*
C50.3699 (5)1.3676 (4)0.3102 (3)0.0458 (8)
H50.27621.42860.28770.055*
C60.3179 (5)1.1802 (4)0.2866 (3)0.0398 (7)
H60.18881.11650.24740.048*
C70.4511 (4)1.0837 (4)0.3192 (2)0.0321 (7)
C80.1477 (4)0.7824 (4)0.1845 (3)0.0343 (7)
C90.0198 (5)0.7292 (5)0.2224 (3)0.0473 (8)
H90.00820.73000.30170.057*
C100.2038 (5)0.6750 (6)0.1453 (4)0.0625 (10)
H100.31550.64010.17200.075*
C110.2194 (5)0.6734 (5)0.0293 (4)0.0630 (11)
H110.34290.63600.02360.076*
C120.0570 (5)0.7259 (5)0.0105 (3)0.0534 (9)
H120.07120.72510.08990.064*
C130.1287 (4)0.7804 (4)0.0654 (3)0.0392 (7)
C140.2810 (7)0.8322 (6)0.0890 (3)0.0724 (12)
H14A0.21890.71000.13910.109*
H14B0.41000.87070.10070.109*
H14C0.20380.91350.10920.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0352 (5)0.0328 (5)0.0440 (5)0.0059 (3)0.0069 (3)0.0084 (3)
O10.0278 (12)0.0501 (14)0.0820 (18)0.0043 (10)0.0036 (11)0.0276 (12)
O20.0338 (11)0.0388 (13)0.0552 (14)0.0085 (10)0.0079 (10)0.0113 (10)
O30.0431 (13)0.0774 (18)0.0416 (13)0.0053 (12)0.0098 (10)0.0160 (12)
C10.0304 (16)0.0372 (18)0.0298 (15)0.0038 (13)0.0022 (12)0.0053 (13)
C20.0331 (15)0.0370 (16)0.0276 (14)0.0075 (13)0.0017 (12)0.0089 (12)
C30.0359 (16)0.0389 (17)0.0421 (17)0.0025 (13)0.0014 (13)0.0093 (14)
C40.053 (2)0.0303 (16)0.050 (2)0.0078 (15)0.0065 (16)0.0087 (14)
C50.0429 (18)0.0429 (19)0.0445 (19)0.0155 (15)0.0069 (15)0.0091 (15)
C60.0355 (16)0.0412 (18)0.0354 (16)0.0109 (13)0.0056 (13)0.0074 (13)
C70.0359 (16)0.0329 (15)0.0264 (14)0.0081 (12)0.0058 (12)0.0084 (12)
C80.0310 (15)0.0295 (15)0.0347 (16)0.0055 (12)0.0000 (12)0.0032 (12)
C90.0403 (18)0.052 (2)0.0449 (19)0.0054 (15)0.0111 (15)0.0102 (15)
C100.0338 (19)0.068 (3)0.082 (3)0.0052 (17)0.0184 (18)0.017 (2)
C110.0327 (19)0.065 (3)0.072 (3)0.0005 (17)0.0086 (18)0.010 (2)
C120.047 (2)0.055 (2)0.0452 (19)0.0022 (16)0.0081 (16)0.0143 (16)
C130.0352 (16)0.0338 (16)0.0413 (17)0.0019 (13)0.0020 (13)0.0086 (13)
C140.085 (3)0.077 (3)0.049 (2)0.002 (2)0.021 (2)0.021 (2)
Geometric parameters (Å, º) top
S1—C81.774 (3)C6—C71.380 (4)
S1—C71.782 (3)C6—H60.9300
O1—C11.311 (3)C8—C91.382 (4)
O1—H10.8200C8—C131.394 (4)
O2—C11.222 (3)C9—C101.379 (5)
O3—C131.349 (4)C9—H90.9300
O3—C141.429 (4)C10—C111.361 (6)
C1—C21.470 (4)C10—H100.9300
C2—C31.398 (4)C11—C121.362 (5)
C2—C71.409 (4)C11—H110.9300
C3—C41.368 (4)C12—C131.382 (4)
C3—H30.9300C12—H120.9300
C4—C51.378 (4)C14—H14A0.9600
C4—H40.9300C14—H14B0.9600
C5—C61.375 (4)C14—H14C0.9600
C5—H50.9300
C8—S1—C7102.44 (13)C9—C8—C13118.9 (3)
C1—O1—H1109.5C9—C8—S1119.1 (2)
C13—O3—C14117.9 (3)C13—C8—S1122.0 (2)
O2—C1—O1122.3 (3)C10—C9—C8121.4 (3)
O2—C1—C2123.6 (3)C10—C9—H9119.3
O1—C1—C2114.2 (3)C8—C9—H9119.3
C3—C2—C7118.9 (3)C11—C10—C9118.9 (3)
C3—C2—C1118.3 (3)C11—C10—H10120.5
C7—C2—C1122.7 (3)C9—C10—H10120.5
C4—C3—C2121.8 (3)C10—C11—C12121.0 (3)
C4—C3—H3119.1C10—C11—H11119.5
C2—C3—H3119.1C12—C11—H11119.5
C3—C4—C5119.0 (3)C11—C12—C13120.9 (3)
C3—C4—H4120.5C11—C12—H12119.5
C5—C4—H4120.5C13—C12—H12119.5
C6—C5—C4120.2 (3)O3—C13—C12124.3 (3)
C6—C5—H5119.9O3—C13—C8116.7 (3)
C4—C5—H5119.9C12—C13—C8118.9 (3)
C5—C6—C7122.1 (3)O3—C14—H14A109.5
C5—C6—H6119.0O3—C14—H14B109.5
C7—C6—H6119.0H14A—C14—H14B109.5
C6—C7—C2118.0 (3)O3—C14—H14C109.5
C6—C7—S1121.3 (2)H14A—C14—H14C109.5
C2—C7—S1120.7 (2)H14B—C14—H14C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.852.658 (3)171
Symmetry code: (i) x+2, y+2, z+1.
 

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