(2E)-1-(2,4-Dichloro­phen­yl)-3-[4-(methyl­sulfan­yl)­phen­yl]prop-2-en-1-one

The title compound, C₁₆H₁₂Cl₂OS, crystallizes in a non-centrosymmetric space group and shows a significant nonlinear optical activity. The source of the optical activity lies in the twist of the chalcone backbone, as exemplified by the dihedral angle of 42.45 (6)° between the two benzene rings. Weak inter­molecular C—H...O hydrogen bonds may contribute to the stabilization of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 103 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.028
• wR factor = 0.071
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H16B   ..  O       ..       3.21 Ang.

Alert level C
PLAT481_ALERT_4_C Long D...A H-Bond Reported C16    ..  O       ..       3.85 Ang.

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           28.11
           From the CIF: _reflns_number_total               2893
           Count of symmetry unique reflns         1967
           Completeness (_total/calc)            147.08%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       926
           Fraction of Friedel pairs measured     0.471
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); 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, 2003); software used to prepare material for publication: SHELXTL.

(2E)-1-(2,4-Dichlorophenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one

Crystal data

C16H12Cl2OS	F(000) = 332
Mr = 323.22	Dx = 1.520 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3886 reflections
a = 12.957 (3) Å	θ = 2.9–28.1°
b = 3.8920 (8) Å	µ = 0.60 mm^−1
c = 14.135 (3) Å	T = 103 K
β = 97.736 (2)°	Rectangular, colorless
V = 706.3 (3) Å^3	0.55 × 0.26 × 0.11 mm
Z = 2

Data collection

Bruker APEX-II CCD area-detector diffractometer	2893 independent reflections
Radiation source: fine-focus sealed tube	2811 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 28.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→17
Tmin = 0.712, Tmax = 0.937	k = −5→3
6061 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.071	w = 1/[σ^2(Fo^2) + (0.0419P)^2 + 0.1565P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2893 reflections	Δρmax = 0.33 e Å^−3
182 parameters	Δρmin = −0.35 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 926 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.16 (6)

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
Cl1	−0.00538 (3)	0.37572 (13)	0.89930 (3)	0.01717 (11)
Cl2	−0.18050 (4)	−0.19704 (15)	0.57168 (3)	0.02374 (14)
S	0.47612 (4)	0.18582 (14)	1.38761 (3)	0.01730 (12)
O	0.27298 (11)	0.4264 (5)	0.77095 (10)	0.0233 (4)
C1	0.10934 (14)	0.1597 (6)	0.76136 (12)	0.0142 (4)
C2	0.01142 (14)	0.1855 (6)	0.79079 (12)	0.0138 (4)
C3	−0.07867 (15)	0.0779 (6)	0.73320 (13)	0.0164 (4)
H3A	−0.1451	0.1013	0.7539	0.020*
C4	−0.06879 (15)	−0.0640 (6)	0.64492 (12)	0.0159 (4)
C5	0.02720 (14)	−0.0971 (6)	0.61312 (12)	0.0172 (4)
H5A	0.0328	−0.1983	0.5529	0.021*
C6	0.11498 (15)	0.0205 (6)	0.67111 (13)	0.0170 (4)
H6A	0.1808	0.0060	0.6488	0.020*
C7	0.21045 (14)	0.2845 (6)	0.81600 (12)	0.0160 (4)
C8	0.23343 (14)	0.2203 (6)	0.91937 (12)	0.0153 (4)
H8A	0.1887	0.0781	0.9504	0.018*
C9	0.31791 (13)	0.3638 (6)	0.96960 (12)	0.0145 (4)
H9A	0.3587	0.5072	0.9348	0.017*
C10	0.35436 (13)	0.3250 (6)	1.07136 (12)	0.0140 (4)
C11	0.29612 (14)	0.1612 (6)	1.13499 (13)	0.0160 (4)
H11A	0.2289	0.0734	1.1123	0.019*
C12	0.33543 (14)	0.1260 (6)	1.23055 (13)	0.0163 (4)
H12A	0.2949	0.0155	1.2728	0.020*
C13	0.43522 (14)	0.2531 (5)	1.26544 (12)	0.0142 (4)
C14	0.49327 (14)	0.4181 (6)	1.20340 (12)	0.0155 (4)
H14A	0.5605	0.5057	1.2261	0.019*
C15	0.45252 (14)	0.4548 (6)	1.10765 (13)	0.0150 (4)
H15A	0.4924	0.5709	1.0658	0.018*
C16	0.60977 (14)	0.3260 (6)	1.40322 (13)	0.0188 (4)
H16A	0.6418	0.2757	1.4686	0.028*
H16B	0.6125	0.5739	1.3917	0.028*
H16C	0.6478	0.2047	1.3579	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0203 (2)	0.0206 (3)	0.01072 (17)	0.00303 (19)	0.00264 (14)	−0.00155 (18)
Cl2	0.0229 (2)	0.0290 (3)	0.0171 (2)	−0.0051 (2)	−0.00527 (16)	−0.00106 (19)
S	0.0194 (2)	0.0212 (3)	0.01093 (19)	−0.0016 (2)	0.00084 (16)	0.00101 (19)
O	0.0193 (7)	0.0326 (11)	0.0178 (6)	−0.0045 (7)	0.0017 (5)	0.0072 (7)
C1	0.0170 (9)	0.0138 (11)	0.0113 (7)	0.0015 (8)	0.0004 (6)	0.0036 (8)
C2	0.0207 (9)	0.0113 (10)	0.0096 (7)	0.0022 (8)	0.0031 (6)	0.0011 (7)
C3	0.0167 (9)	0.0189 (11)	0.0137 (8)	0.0006 (8)	0.0023 (7)	0.0034 (7)
C4	0.0201 (9)	0.0136 (11)	0.0122 (7)	−0.0016 (8)	−0.0041 (6)	0.0026 (7)
C5	0.0243 (10)	0.0162 (12)	0.0110 (8)	0.0013 (9)	0.0020 (7)	0.0010 (8)
C6	0.0194 (9)	0.0182 (11)	0.0136 (8)	0.0033 (8)	0.0031 (7)	0.0031 (8)
C7	0.0177 (8)	0.0164 (11)	0.0138 (8)	0.0020 (8)	0.0016 (6)	0.0011 (7)
C8	0.0187 (9)	0.0142 (11)	0.0129 (8)	0.0020 (8)	0.0013 (7)	0.0032 (8)
C9	0.0156 (8)	0.0146 (11)	0.0133 (7)	0.0025 (8)	0.0022 (6)	0.0013 (8)
C10	0.0148 (8)	0.0135 (11)	0.0132 (8)	0.0025 (8)	0.0005 (6)	−0.0004 (7)
C11	0.0140 (8)	0.0182 (11)	0.0153 (8)	−0.0021 (8)	0.0000 (6)	−0.0017 (8)
C12	0.0191 (9)	0.0169 (12)	0.0134 (8)	−0.0027 (8)	0.0038 (7)	0.0000 (8)
C13	0.0183 (8)	0.0106 (11)	0.0134 (8)	0.0019 (7)	0.0015 (6)	−0.0014 (7)
C14	0.0147 (8)	0.0163 (12)	0.0151 (8)	−0.0029 (8)	0.0002 (6)	−0.0004 (8)
C15	0.0166 (9)	0.0151 (11)	0.0137 (8)	−0.0004 (8)	0.0039 (6)	0.0013 (7)
C16	0.0189 (9)	0.0212 (12)	0.0156 (8)	−0.0007 (9)	−0.0004 (6)	−0.0029 (8)

Geometric parameters (Å, º)

Cl1—C2	1.7430 (19)	C8—H8A	0.9500
Cl2—C4	1.7411 (19)	C9—C10	1.460 (2)
S—C13	1.7564 (18)	C9—H9A	0.9500
S—C16	1.801 (2)	C10—C15	1.400 (3)
O—C7	1.227 (2)	C10—C11	1.403 (3)
C1—C2	1.391 (2)	C11—C12	1.385 (2)
C1—C6	1.397 (3)	C11—H11A	0.9500
C1—C7	1.509 (2)	C12—C13	1.410 (3)
C2—C3	1.395 (3)	C12—H12A	0.9500
C3—C4	1.386 (3)	C13—C14	1.387 (3)
C3—H3A	0.9500	C14—C15	1.392 (2)
C4—C5	1.384 (3)	C14—H14A	0.9500
C5—C6	1.387 (3)	C15—H15A	0.9500
C5—H5A	0.9500	C16—H16A	0.9800
C6—H6A	0.9500	C16—H16B	0.9800
C7—C8	1.473 (2)	C16—H16C	0.9800
C8—C9	1.343 (3)
C13—S—C16	103.49 (9)	C8—C9—H9A	116.2
C2—C1—C6	117.58 (16)	C10—C9—H9A	116.2
C2—C1—C7	126.01 (17)	C15—C10—C11	118.00 (16)
C6—C1—C7	116.34 (16)	C15—C10—C9	118.75 (17)
C1—C2—C3	121.96 (17)	C11—C10—C9	123.24 (17)
C1—C2—Cl1	121.38 (14)	C12—C11—C10	120.77 (18)
C3—C2—Cl1	116.58 (14)	C12—C11—H11A	119.6
C4—C3—C2	118.27 (17)	C10—C11—H11A	119.6
C4—C3—H3A	120.9	C11—C12—C13	120.40 (18)
C2—C3—H3A	120.9	C11—C12—H12A	119.8
C5—C4—C3	121.69 (16)	C13—C12—H12A	119.8
C5—C4—Cl2	119.38 (14)	C14—C13—C12	119.39 (17)
C3—C4—Cl2	118.92 (15)	C14—C13—S	124.96 (14)
C4—C5—C6	118.58 (17)	C12—C13—S	115.64 (14)
C4—C5—H5A	120.7	C13—C14—C15	119.67 (17)
C6—C5—H5A	120.7	C13—C14—H14A	120.2
C5—C6—C1	121.88 (17)	C15—C14—H14A	120.2
C5—C6—H6A	119.1	C14—C15—C10	121.75 (18)
C1—C6—H6A	119.1	C14—C15—H15A	119.1
O—C7—C8	122.12 (17)	C10—C15—H15A	119.1
O—C7—C1	117.89 (16)	S—C16—H16A	109.5
C8—C7—C1	119.93 (17)	S—C16—H16B	109.5
C9—C8—C7	119.70 (18)	H16A—C16—H16B	109.5
C9—C8—H8A	120.2	S—C16—H16C	109.5
C7—C8—H8A	120.2	H16A—C16—H16C	109.5
C8—C9—C10	127.60 (18)	H16B—C16—H16C	109.5
C6—C1—C2—C3	−0.1 (3)	O—C7—C8—C9	10.2 (3)
C7—C1—C2—C3	176.7 (2)	C1—C7—C8—C9	−172.7 (2)
C6—C1—C2—Cl1	−176.58 (16)	C7—C8—C9—C10	−178.69 (19)
C7—C1—C2—Cl1	0.2 (3)	C8—C9—C10—C15	170.7 (2)
C1—C2—C3—C4	1.2 (3)	C8—C9—C10—C11	−8.8 (4)
Cl1—C2—C3—C4	177.84 (17)	C15—C10—C11—C12	−0.8 (3)
C2—C3—C4—C5	−0.6 (3)	C9—C10—C11—C12	178.8 (2)
C2—C3—C4—Cl2	−179.57 (17)	C10—C11—C12—C13	−0.3 (3)
C3—C4—C5—C6	−1.0 (3)	C11—C12—C13—C14	0.9 (3)
Cl2—C4—C5—C6	177.92 (17)	C11—C12—C13—S	−179.15 (17)
C4—C5—C6—C1	2.2 (3)	C16—S—C13—C14	−7.2 (2)
C2—C1—C6—C5	−1.6 (3)	C16—S—C13—C12	172.80 (16)
C7—C1—C6—C5	−178.8 (2)	C12—C13—C14—C15	−0.3 (3)
C2—C1—C7—O	−139.1 (2)	S—C13—C14—C15	179.74 (16)
C6—C1—C7—O	37.8 (3)	C13—C14—C15—C10	−0.9 (3)
C2—C1—C7—C8	43.7 (3)	C11—C10—C15—C14	1.4 (3)
C6—C1—C7—C8	−139.5 (2)	C9—C10—C15—C14	−178.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O^i	0.98	3.21	3.852 (3)	125

Symmetry code: (i) −x+1, y+1/2, −z+2.