2-[(4-Chloro­phen­yl)sulfan­yl]-2-meth­oxy-1-phenyl­ethan-1-one: crystal structure and Hirshfeld surface analysis

A chiral methine-C atom connects the (4-chloro­phen­yl)sulfanyl, benzaldehyde and meth­oxy residues in the racemic title compound. Supra­molecular helical chains are formed in the crystal, being sustained by methyl- and methine-C—H...O(carbon­yl) inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.048
• wR factor = 0.116
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full           ! Check
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       7.32 Note
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00957 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.594         54 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         70 %
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT792_ALERT_1_G Model has Chirality at C8        (Polar  SPGR)            R Verify

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   4 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.
PUBL022_ALERT_1_A There is a mismatched ~ on line 319
              vase-shaped distribution of points beginning at <i>d</i>~e~ + <i>d</i>~i~ \~
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   2 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

2-[(4-Chlorophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one

Crystal data

C15H13ClO2S	Dx = 1.380 Mg m^−3
Mr = 292.76	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 1839 reflections
a = 17.964 (3) Å	θ = 2.5–23.7°
b = 8.0234 (15) Å	µ = 0.41 mm^−1
c = 9.7761 (19) Å	T = 293 K
V = 1409.0 (5) Å^3	Irregular, colourless
Z = 4	0.42 × 0.21 × 0.12 mm
F(000) = 608

Data collection

Bruker APEXII CCD diffractometer	1505 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.049
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 25.0°, θmin = 2.3°
Tmin = 0.365, Tmax = 0.745	h = −20→21
5010 measured reflections	k = −7→9
2081 independent reflections	l = −11→8

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)] = 0.048	w = 1/[σ^2(Fo^2) + (0.043P)^2 + 0.3264P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.116	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.28 e Å^−3
2081 reflections	Δρmin = −0.18 e Å^−3
173 parameters	Absolute structure: Flack x determined using 465 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.06 (9)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.36121 (11)	0.3177 (3)	1.0687 (2)	0.0916 (7)
S1	0.41934 (10)	0.2492 (2)	0.4390 (2)	0.0646 (5)
O1	0.5511 (2)	0.0919 (5)	0.4909 (4)	0.0616 (11)
O2	0.4654 (2)	−0.1253 (5)	0.6070 (4)	0.0685 (12)
C1	0.3786 (4)	0.2943 (8)	0.8946 (7)	0.0571 (17)
C2	0.3254 (4)	0.2193 (8)	0.8147 (9)	0.069 (2)
H2	0.2812	0.1806	0.8527	0.083*
C3	0.3396 (4)	0.2028 (8)	0.6744 (8)	0.0644 (18)
H3	0.3048	0.1506	0.6186	0.077*
C4	0.4045 (3)	0.2632 (7)	0.6186 (7)	0.0529 (15)
C5	0.4565 (4)	0.3385 (7)	0.7019 (7)	0.0579 (16)
H5	0.5005	0.3793	0.6647	0.069*
C6	0.4432 (4)	0.3534 (8)	0.8404 (7)	0.0593 (18)
H6	0.4784	0.4038	0.8967	0.071*
C7	0.6003 (4)	0.1950 (9)	0.4167 (9)	0.081 (2)
H7A	0.6078	0.1492	0.3271	0.121*
H7B	0.6472	0.2011	0.4637	0.121*
H7C	0.5794	0.3047	0.4090	0.121*
C8	0.4828 (3)	0.0677 (6)	0.4279 (7)	0.0504 (14)
H8	0.4915	0.0421	0.3312	0.060*
C9	0.4447 (3)	−0.0804 (7)	0.4942 (6)	0.0493 (14)
C10	0.3836 (3)	−0.1693 (7)	0.4225 (7)	0.0465 (13)
C11	0.3538 (3)	−0.3095 (7)	0.4869 (7)	0.0577 (16)
H11	0.3719	−0.3431	0.5716	0.069*
C12	0.2974 (3)	−0.3981 (7)	0.4246 (9)	0.0690 (18)
H12	0.2784	−0.4924	0.4674	0.083*
C13	0.2691 (4)	−0.3500 (9)	0.3017 (9)	0.073 (2)
H13	0.2306	−0.4097	0.2613	0.087*
C14	0.2984 (4)	−0.2114 (9)	0.2377 (8)	0.075 (2)
H14	0.2794	−0.1774	0.1537	0.090*
C15	0.3559 (3)	−0.1224 (8)	0.2978 (7)	0.0621 (17)
H15	0.3758	−0.0303	0.2531	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1147 (15)	0.1100 (15)	0.0501 (11)	0.0357 (11)	0.0107 (12)	−0.0064 (10)
S1	0.0977 (11)	0.0519 (8)	0.0441 (8)	0.0100 (8)	−0.0060 (11)	0.0053 (8)
O1	0.072 (3)	0.068 (3)	0.045 (3)	−0.012 (2)	−0.002 (2)	0.001 (2)
O2	0.103 (3)	0.066 (3)	0.037 (3)	−0.010 (2)	−0.008 (3)	0.009 (2)
C1	0.074 (4)	0.054 (4)	0.042 (4)	0.022 (3)	0.005 (4)	−0.003 (3)
C2	0.075 (5)	0.061 (4)	0.071 (5)	0.002 (3)	0.014 (4)	−0.002 (4)
C3	0.073 (4)	0.054 (4)	0.066 (5)	0.000 (3)	−0.005 (4)	−0.006 (3)
C4	0.074 (4)	0.036 (3)	0.048 (4)	0.009 (3)	−0.003 (4)	0.001 (3)
C5	0.068 (4)	0.051 (4)	0.055 (4)	0.005 (3)	0.001 (4)	−0.004 (3)
C6	0.068 (4)	0.058 (4)	0.052 (4)	0.014 (3)	−0.010 (3)	−0.015 (3)
C7	0.087 (5)	0.092 (5)	0.063 (6)	−0.026 (4)	0.004 (5)	−0.004 (5)
C8	0.068 (3)	0.049 (3)	0.034 (3)	0.001 (3)	0.003 (3)	0.003 (3)
C9	0.075 (4)	0.046 (3)	0.028 (3)	0.009 (3)	0.009 (3)	0.002 (3)
C10	0.061 (3)	0.044 (3)	0.035 (3)	0.006 (3)	0.006 (3)	−0.002 (3)
C11	0.067 (4)	0.056 (4)	0.050 (4)	0.005 (3)	0.004 (3)	0.008 (3)
C12	0.073 (4)	0.053 (4)	0.081 (6)	−0.007 (3)	0.012 (5)	0.005 (4)
C13	0.073 (5)	0.076 (5)	0.069 (5)	−0.011 (3)	0.002 (4)	−0.011 (4)
C14	0.088 (5)	0.092 (5)	0.046 (5)	−0.003 (4)	−0.010 (4)	−0.006 (4)
C15	0.082 (4)	0.059 (4)	0.046 (4)	−0.013 (3)	−0.003 (4)	0.001 (3)

Geometric parameters (Å, º)

Cl1—C1	1.741 (7)	C7—H7B	0.9600
S1—C4	1.780 (7)	C7—H7C	0.9600
S1—C8	1.853 (5)	C8—C9	1.517 (7)
O1—C8	1.386 (6)	C8—H8	0.9800
O1—C7	1.412 (8)	C9—C10	1.485 (8)
O2—C9	1.219 (7)	C10—C15	1.370 (9)
C1—C6	1.362 (9)	C10—C11	1.395 (8)
C1—C2	1.372 (10)	C11—C12	1.379 (9)
C2—C3	1.401 (10)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.360 (11)
C3—C4	1.376 (9)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.380 (9)
C4—C5	1.378 (8)	C13—H13	0.9300
C5—C6	1.381 (9)	C14—C15	1.387 (8)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—H7A	0.9600
C4—S1—C8	101.5 (3)	O1—C8—S1	114.1 (4)
C8—O1—C7	114.1 (5)	C9—C8—S1	108.2 (4)
C6—C1—C2	121.6 (7)	O1—C8—H8	108.6
C6—C1—Cl1	119.7 (6)	C9—C8—H8	108.6
C2—C1—Cl1	118.6 (6)	S1—C8—H8	108.6
C1—C2—C3	118.2 (7)	O2—C9—C10	120.7 (5)
C1—C2—H2	120.9	O2—C9—C8	118.8 (5)
C3—C2—H2	120.9	C10—C9—C8	120.6 (5)
C4—C3—C2	120.6 (6)	C15—C10—C11	118.9 (6)
C4—C3—H3	119.7	C15—C10—C9	123.8 (5)
C2—C3—H3	119.7	C11—C10—C9	117.3 (5)
C3—C4—C5	119.6 (7)	C12—C11—C10	119.9 (7)
C3—C4—S1	119.7 (5)	C12—C11—H11	120.0
C5—C4—S1	120.6 (5)	C10—C11—H11	120.0
C4—C5—C6	120.0 (6)	C13—C12—C11	121.2 (6)
C4—C5—H5	120.0	C13—C12—H12	119.4
C6—C5—H5	120.0	C11—C12—H12	119.4
C1—C6—C5	119.9 (6)	C12—C13—C14	119.1 (7)
C1—C6—H6	120.1	C12—C13—H13	120.5
C5—C6—H6	120.1	C14—C13—H13	120.5
O1—C7—H7A	109.5	C13—C14—C15	120.5 (7)
O1—C7—H7B	109.5	C13—C14—H14	119.8
H7A—C7—H7B	109.5	C15—C14—H14	119.8
O1—C7—H7C	109.5	C10—C15—C14	120.4 (6)
H7A—C7—H7C	109.5	C10—C15—H15	119.8
H7B—C7—H7C	109.5	C14—C15—H15	119.8
O1—C8—C9	108.6 (5)
C6—C1—C2—C3	0.8 (9)	O1—C8—C9—O2	19.3 (7)
Cl1—C1—C2—C3	179.3 (5)	S1—C8—C9—O2	−105.1 (5)
C1—C2—C3—C4	−1.2 (9)	O1—C8—C9—C10	−160.4 (5)
C2—C3—C4—C5	0.9 (9)	S1—C8—C9—C10	75.2 (6)
C2—C3—C4—S1	−177.2 (5)	O2—C9—C10—C15	177.7 (6)
C8—S1—C4—C3	−101.5 (5)	C8—C9—C10—C15	−2.5 (8)
C8—S1—C4—C5	80.5 (5)	O2—C9—C10—C11	−2.9 (8)
C3—C4—C5—C6	−0.2 (8)	C8—C9—C10—C11	176.9 (5)
S1—C4—C5—C6	177.9 (5)	C15—C10—C11—C12	0.0 (9)
C2—C1—C6—C5	0.0 (9)	C9—C10—C11—C12	−179.4 (5)
Cl1—C1—C6—C5	−178.5 (5)	C10—C11—C12—C13	−1.0 (9)
C4—C5—C6—C1	−0.3 (9)	C11—C12—C13—C14	1.0 (10)
C7—O1—C8—C9	163.9 (5)	C12—C13—C14—C15	0.1 (10)
C7—O1—C8—S1	−75.3 (6)	C11—C10—C15—C14	1.0 (10)
C4—S1—C8—O1	−63.7 (4)	C9—C10—C15—C14	−179.6 (5)
C4—S1—C8—C9	57.3 (5)	C13—C14—C15—C10	−1.1 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2^i	0.96	2.53	3.297 (9)	137
C8—H8···O2^i	0.98	2.42	3.305 (8)	150

Symmetry code: (i) −x+1, −y, z−1/2.