4-Chloro­phenyl thio­benzoate

The title compound, C₁₃H₉ClOS, crystallizes in the ortho­rhombic system in the non-centrosymmetric space group P2₁2₁2₁, with one molecule in the asymmetric unit. The repulsion between two Cl atoms of neighbouring molecules is minimized by a 2₁ screw arrangement of the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.037
• wR factor = 0.096
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing ..          ?

Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.95
           From the CIF: _reflns_number_total               1912
           Count of symmetry unique reflns         1524
           Completeness (_total/calc)            125.46%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       388
           Fraction of Friedel pairs measured     0.255
           Are heavy atom types Z>Si present        yes

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, (1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

4-Chlorophenyl thiobenzoate

Crystal data

C13H9ClOS	Dx = 1.381 Mg m^−3 Dm = 1.38 Mg m^−3 Dm measured by flotation in a mixture of carbon tetrachloride and xylene
Mr = 248.71	Melting point: 373 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 5.8410 (5) Å	θ = 10.1–14.1°
b = 13.3630 (11) Å	µ = 0.47 mm^−1
c = 15.3250 (17) Å	T = 293 K
V = 1196.17 (19) Å^3	Needle, colourless
Z = 4	0.25 × 0.2 × 0.15 mm
F(000) = 512

Data collection

Nonius MACH3 sealed-tube diffractometer	1338 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 27.0°, θmin = 2.0°
ω–2θ scans	h = −1→7
Absorption correction: ψ scan (North et al., 1968)	k = −1→17
Tmin = 0.862, Tmax = 0.932	l = −1→19
2084 measured reflections	3 standard reflections every 60 min
1912 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0358P)^2 + 0.4019P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.096	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.26 e Å^−3
1912 reflections	Δρmin = −0.27 e Å^−3
146 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0085 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 388 Friedel pairs?
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.04 (13)

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	0.2576 (6)	0.2208 (2)	0.4235 (2)	0.0609 (9)
H1	0.3879	0.2006	0.4537	0.073*
C2	0.2287 (6)	0.3207 (2)	0.4009 (2)	0.0631 (9)
H2	0.3395	0.3678	0.4155	0.076*
C3	0.0356 (6)	0.3489 (2)	0.3570 (2)	0.0576 (8)
Cl1	−0.0020 (2)	0.47375 (7)	0.32915 (7)	0.0970 (4)
C4	−0.1297 (7)	0.2806 (3)	0.3334 (2)	0.0655 (9)
H4	−0.2595	0.3010	0.3031	0.079*
C5	−0.0996 (7)	0.1816 (3)	0.3554 (2)	0.0666 (9)
H5	−0.2093	0.1347	0.3394	0.080*
C6	0.0916 (6)	0.1515 (2)	0.4010 (2)	0.0571 (8)
S1	0.1099 (2)	0.02496 (7)	0.43453 (6)	0.0836 (4)
C7	0.3421 (6)	−0.0179 (3)	0.36933 (19)	0.0579 (8)
O1	0.4504 (4)	0.03712 (17)	0.32328 (17)	0.0812 (7)
C8	0.3861 (6)	−0.1277 (2)	0.37399 (17)	0.0525 (7)
C9	0.5841 (6)	−0.1646 (2)	0.3358 (2)	0.0649 (9)
H9	0.6903	−0.1206	0.3119	0.078*
C10	0.6244 (7)	−0.2665 (3)	0.3332 (2)	0.0702 (10)
H10	0.7560	−0.2908	0.3064	0.084*
C11	0.4708 (8)	−0.3320 (3)	0.3699 (2)	0.0725 (11)
H11	0.4979	−0.4005	0.3681	0.087*
C12	0.2761 (7)	−0.2953 (3)	0.4095 (2)	0.0709 (10)
H12	0.1731	−0.3394	0.4352	0.085*
C13	0.2327 (6)	−0.1943 (2)	0.4115 (2)	0.0644 (9)
H13	0.1002	−0.1706	0.4381	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.049 (2)	0.073 (2)	0.061 (2)	0.0059 (18)	−0.0062 (18)	−0.0039 (17)
C2	0.057 (2)	0.067 (2)	0.066 (2)	−0.0120 (19)	−0.0037 (19)	−0.0092 (17)
C3	0.058 (2)	0.0576 (17)	0.0572 (17)	0.0025 (18)	0.0035 (17)	0.0024 (14)
Cl1	0.1120 (9)	0.0671 (5)	0.1117 (8)	0.0125 (6)	0.0062 (7)	0.0156 (6)
C4	0.0494 (19)	0.085 (2)	0.0621 (19)	−0.002 (2)	−0.005 (2)	0.0087 (18)
C5	0.057 (2)	0.077 (2)	0.0662 (19)	−0.020 (2)	0.002 (2)	−0.0038 (17)
C6	0.060 (2)	0.0591 (17)	0.0527 (16)	0.0006 (18)	0.0113 (18)	−0.0021 (14)
S1	0.1050 (8)	0.0614 (5)	0.0845 (6)	0.0088 (6)	0.0441 (6)	0.0075 (5)
C7	0.0544 (18)	0.0622 (17)	0.0571 (16)	−0.0065 (18)	0.0011 (15)	−0.0016 (16)
O1	0.0656 (16)	0.0693 (14)	0.1087 (18)	−0.0120 (14)	0.0255 (16)	0.0049 (14)
C8	0.0485 (18)	0.0594 (17)	0.0496 (16)	−0.0010 (17)	−0.0034 (16)	−0.0044 (13)
C9	0.056 (2)	0.070 (2)	0.068 (2)	−0.0036 (18)	0.004 (2)	−0.0026 (18)
C10	0.057 (2)	0.077 (2)	0.076 (2)	0.010 (2)	0.002 (2)	−0.008 (2)
C11	0.088 (3)	0.061 (2)	0.068 (2)	0.011 (2)	−0.007 (2)	−0.0023 (17)
C12	0.079 (3)	0.061 (2)	0.072 (2)	−0.008 (2)	0.008 (2)	0.0041 (18)
C13	0.063 (2)	0.0658 (19)	0.065 (2)	−0.002 (2)	0.0147 (19)	−0.0015 (17)

Geometric parameters (Å, º)

C1—C6	1.385 (4)	C7—O1	1.200 (4)
C1—C2	1.389 (5)	C7—C8	1.491 (4)
C1—H1	0.9300	C8—C9	1.387 (4)
C2—C3	1.366 (5)	C8—C13	1.388 (4)
C2—H2	0.9300	C9—C10	1.382 (4)
C3—C4	1.377 (5)	C9—H9	0.9300
C3—Cl1	1.736 (3)	C10—C11	1.374 (5)
C4—C5	1.376 (5)	C10—H10	0.9300
C4—H4	0.9300	C11—C12	1.379 (5)
C5—C6	1.377 (5)	C11—H11	0.9300
C5—H5	0.9300	C12—C13	1.373 (5)
C6—S1	1.771 (3)	C12—H12	0.9300
S1—C7	1.780 (4)	C13—H13	0.9300
C6—C1—C2	119.7 (3)	O1—C7—S1	122.3 (3)
C6—C1—H1	120.2	C8—C7—S1	114.9 (2)
C2—C1—H1	120.2	C9—C8—C13	119.0 (3)
C3—C2—C1	119.2 (3)	C9—C8—C7	118.2 (3)
C3—C2—H2	120.4	C13—C8—C7	122.7 (3)
C1—C2—H2	120.4	C10—C9—C8	120.3 (3)
C2—C3—C4	121.7 (3)	C10—C9—H9	119.8
C2—C3—Cl1	119.4 (3)	C8—C9—H9	119.8
C4—C3—Cl1	118.9 (3)	C11—C10—C9	120.3 (4)
C5—C4—C3	118.9 (4)	C11—C10—H10	119.9
C5—C4—H4	120.6	C9—C10—H10	119.9
C3—C4—H4	120.6	C10—C11—C12	119.5 (3)
C4—C5—C6	120.6 (3)	C10—C11—H11	120.3
C4—C5—H5	119.7	C12—C11—H11	120.3
C6—C5—H5	119.7	C13—C12—C11	120.8 (4)
C5—C6—C1	119.9 (3)	C13—C12—H12	119.6
C5—C6—S1	118.4 (3)	C11—C12—H12	119.6
C1—C6—S1	121.6 (3)	C12—C13—C8	120.1 (3)
C6—S1—C7	101.00 (16)	C12—C13—H13	119.9
O1—C7—C8	122.7 (3)	C8—C13—H13	119.9
C6—C1—C2—C3	0.3 (5)	C6—S1—C7—C8	−173.0 (2)
C1—C2—C3—C4	−1.0 (5)	O1—C7—C8—C9	11.7 (5)
C1—C2—C3—Cl1	179.7 (3)	S1—C7—C8—C9	−170.4 (2)
C2—C3—C4—C5	0.5 (5)	O1—C7—C8—C13	−165.5 (3)
Cl1—C3—C4—C5	179.9 (3)	S1—C7—C8—C13	12.4 (4)
C3—C4—C5—C6	0.6 (5)	C13—C8—C9—C10	1.8 (5)
C4—C5—C6—C1	−1.3 (5)	C7—C8—C9—C10	−175.5 (3)
C4—C5—C6—S1	175.3 (3)	C8—C9—C10—C11	−1.3 (5)
C2—C1—C6—C5	0.8 (5)	C9—C10—C11—C12	0.0 (5)
C2—C1—C6—S1	−175.6 (3)	C10—C11—C12—C13	0.9 (5)
C5—C6—S1—C7	112.9 (3)	C11—C12—C13—C8	−0.5 (6)
C1—C6—S1—C7	−70.5 (3)	C9—C8—C13—C12	−0.9 (5)
C6—S1—C7—O1	4.9 (3)	C7—C8—C13—C12	176.3 (3)