(2E)-3-Anilino-1-(2-chloro­phen­yl)-3-(methyl­sulfan­yl)prop-2-en-1-one

In the title compound, C₁₆H₁₄ClNOS, the dihedral angle between the aromatic rings is 86.34 (9)° and an intra­molecular N—H...O hydrogen bond closes an S(6) ring. The methyl­sulfanyl group and Cl atom lie to the same side of the mol­ecule. In the crystal, C—H...O hydrogen bonds link the mol­ecules into (010) double sheets.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.133
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C3     --  C4      ..        7.7 s.u.

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5855
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.586         32 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          83 % Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Note

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

   2 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
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(2E)-3-Anilino-1-(2-chlorophenyl)-3-(methylsulfanyl)prop-2-en-1-one

Crystal data

C16H14ClNOS	Dx = 1.324 Mg m^−3
Mr = 303.79	Melting point: 461 K
Orthorhombic, Pccn	Cu Kα radiation, λ = 1.54178 Å
a = 15.9745 (6) Å	Cell parameters from 2521 reflections
b = 25.7276 (10) Å	θ = 5.5–64.5°
c = 7.4153 (3) Å	µ = 3.45 mm^−1
V = 3047.6 (2) Å^3	T = 293 K
Z = 8	Prism, colourless
F(000) = 1264	0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer	2521 independent reflections
Radiation source: fine-focus sealed tube	2372 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω and φ scans	θmax = 64.5°, θmin = 5.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −17→17
Tmin = 0.770, Tmax = 1.000	k = −29→29
19433 measured reflections	l = −8→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.079P)^2 + 1.4469P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2521 reflections	Δρmax = 0.49 e Å^−3
181 parameters	Δρmin = −0.46 e Å^−3
0 restraints

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
S11	0.80692 (3)	0.46779 (2)	0.21016 (8)	0.0459 (2)
O8	0.54141 (10)	0.53861 (6)	0.2078 (3)	0.0576 (5)
N13	0.64227 (11)	0.45814 (7)	0.1896 (3)	0.0434 (4)
H13	0.5930	0.4716	0.1870	0.052*
C10	0.70480 (13)	0.49199 (8)	0.2154 (2)	0.0359 (5)
C14	0.64485 (12)	0.40362 (7)	0.1658 (3)	0.0383 (5)
C15	0.59380 (14)	0.38200 (9)	0.0350 (3)	0.0479 (5)
H15	0.5597	0.4032	−0.0352	0.057*
C1	0.63779 (15)	0.66268 (9)	0.2213 (3)	0.0478 (5)
C6	0.59290 (13)	0.62072 (9)	0.2879 (3)	0.0421 (5)
C18	0.69367 (16)	0.31856 (10)	0.2422 (4)	0.0554 (6)
H18	0.7276	0.2971	0.3120	0.066*
C16	0.59351 (17)	0.32902 (10)	0.0088 (4)	0.0567 (6)
H16	0.5589	0.3146	−0.0788	0.068*
C9	0.68755 (13)	0.54435 (8)	0.2402 (3)	0.0389 (5)
H9	0.7321	0.5670	0.2592	0.047*
C12	0.86963 (15)	0.52501 (10)	0.2226 (4)	0.0572 (6)
H12A	0.9278	0.5156	0.2206	0.086*
H12B	0.8575	0.5470	0.1215	0.086*
H12C	0.8574	0.5432	0.3325	0.086*
C19	0.69407 (16)	0.37150 (9)	0.2720 (3)	0.0492 (6)
H19	0.7272	0.3856	0.3629	0.059*
C2	0.62222 (19)	0.71335 (10)	0.2789 (4)	0.0627 (7)
H2	0.6531	0.7409	0.2323	0.075*
C7	0.60564 (13)	0.56482 (8)	0.2381 (3)	0.0400 (5)
C17	0.64396 (15)	0.29716 (9)	0.1111 (4)	0.0553 (6)
H17	0.6443	0.2615	0.0913	0.066*
C5	0.53032 (18)	0.63185 (11)	0.4144 (4)	0.0628 (7)
H5	0.4980	0.6049	0.4607	0.075*
C4	0.5158 (2)	0.68208 (15)	0.4713 (4)	0.0821 (10)
H4	0.4744	0.6886	0.5566	0.099*
C3	0.5617 (2)	0.72210 (12)	0.4031 (4)	0.0741 (9)
H3	0.5514	0.7558	0.4423	0.089*
Cl20	0.71297 (6)	0.65572 (3)	0.05499 (12)	0.0822 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S11	0.0398 (4)	0.0438 (4)	0.0543 (4)	0.0122 (2)	0.0001 (2)	0.0011 (2)
O8	0.0343 (9)	0.0455 (9)	0.0931 (13)	0.0023 (7)	−0.0026 (8)	0.0005 (8)
N13	0.0386 (10)	0.0337 (9)	0.0579 (11)	0.0046 (7)	−0.0030 (8)	0.0017 (8)
C10	0.0368 (11)	0.0376 (11)	0.0335 (10)	0.0042 (8)	−0.0009 (7)	0.0033 (8)
C14	0.0393 (11)	0.0339 (10)	0.0415 (10)	0.0003 (8)	0.0024 (8)	0.0021 (8)
C15	0.0420 (12)	0.0465 (12)	0.0551 (13)	−0.0084 (9)	−0.0074 (10)	0.0094 (10)
C1	0.0497 (13)	0.0409 (12)	0.0528 (13)	0.0074 (10)	−0.0064 (10)	−0.0030 (9)
C6	0.0400 (11)	0.0429 (12)	0.0432 (11)	0.0123 (9)	−0.0043 (9)	−0.0025 (9)
C18	0.0613 (16)	0.0370 (12)	0.0678 (15)	0.0046 (10)	−0.0090 (12)	0.0058 (11)
C16	0.0594 (15)	0.0526 (13)	0.0581 (13)	−0.0193 (11)	−0.0075 (12)	−0.0027 (11)
C9	0.0345 (11)	0.0350 (11)	0.0471 (11)	0.0019 (8)	0.0003 (8)	−0.0010 (9)
C12	0.0347 (12)	0.0616 (15)	0.0752 (17)	0.0035 (11)	−0.0053 (11)	0.0037 (12)
C19	0.0609 (15)	0.0388 (12)	0.0480 (12)	0.0009 (10)	−0.0136 (10)	0.0010 (9)
C2	0.0687 (17)	0.0427 (13)	0.0767 (17)	0.0126 (12)	−0.0213 (14)	−0.0101 (12)
C7	0.0358 (11)	0.0388 (11)	0.0454 (11)	0.0034 (9)	0.0013 (8)	0.0025 (8)
C17	0.0603 (15)	0.0360 (11)	0.0696 (15)	−0.0063 (10)	0.0040 (12)	−0.0062 (11)
C5	0.0584 (15)	0.0699 (16)	0.0601 (14)	0.0232 (13)	0.0038 (12)	−0.0044 (13)
C4	0.080 (2)	0.102 (3)	0.0648 (17)	0.047 (2)	0.0060 (15)	−0.0224 (17)
C3	0.085 (2)	0.0623 (17)	0.0748 (18)	0.0291 (16)	−0.0190 (16)	−0.0257 (15)
Cl20	0.0963 (6)	0.0550 (4)	0.0954 (6)	0.0047 (3)	0.0439 (4)	0.0124 (3)

Geometric parameters (Å, º)

S11—C10	1.747 (2)	C18—H18	0.9300
S11—C12	1.783 (3)	C16—C17	1.377 (4)
O8—C7	1.248 (3)	C16—H16	0.9300
N13—C10	1.339 (3)	C9—C7	1.411 (3)
N13—C14	1.414 (3)	C9—H9	0.9300
N13—H13	0.8600	C12—H12A	0.9600
C10—C9	1.387 (3)	C12—H12B	0.9600
C14—C15	1.384 (3)	C12—H12C	0.9600
C14—C19	1.386 (3)	C19—H19	0.9300
C15—C16	1.377 (3)	C2—C3	1.354 (5)
C15—H15	0.9300	C2—H2	0.9300
C1—C6	1.387 (3)	C17—H17	0.9300
C1—C2	1.394 (3)	C5—C4	1.379 (4)
C1—Cl20	1.731 (3)	C5—H5	0.9300
C6—C5	1.400 (3)	C4—C3	1.362 (5)
C6—C7	1.499 (3)	C4—H4	0.9300
C18—C17	1.371 (4)	C3—H3	0.9300
C18—C19	1.380 (3)
C10—S11—C12	103.25 (11)	S11—C12—H12A	109.5
C10—N13—C14	129.89 (18)	S11—C12—H12B	109.5
C10—N13—H13	115.1	H12A—C12—H12B	109.5
C14—N13—H13	115.1	S11—C12—H12C	109.5
N13—C10—C9	120.16 (19)	H12A—C12—H12C	109.5
N13—C10—S11	117.49 (16)	H12B—C12—H12C	109.5
C9—C10—S11	122.32 (16)	C18—C19—C14	119.7 (2)
C15—C14—C19	119.5 (2)	C18—C19—H19	120.2
C15—C14—N13	117.94 (18)	C14—C19—H19	120.2
C19—C14—N13	122.49 (19)	C3—C2—C1	119.4 (3)
C16—C15—C14	119.9 (2)	C3—C2—H2	120.3
C16—C15—H15	120.0	C1—C2—H2	120.3
C14—C15—H15	120.0	O8—C7—C9	124.24 (19)
C6—C1—C2	121.8 (2)	O8—C7—C6	116.82 (19)
C6—C1—Cl20	122.15 (17)	C9—C7—C6	118.79 (19)
C2—C1—Cl20	116.0 (2)	C18—C17—C16	119.4 (2)
C1—C6—C5	116.7 (2)	C18—C17—H17	120.3
C1—C6—C7	126.07 (19)	C16—C17—H17	120.3
C5—C6—C7	117.3 (2)	C4—C5—C6	121.1 (3)
C17—C18—C19	120.8 (2)	C4—C5—H5	119.4
C17—C18—H18	119.6	C6—C5—H5	119.4
C19—C18—H18	119.6	C3—C4—C5	120.3 (3)
C15—C16—C17	120.7 (2)	C3—C4—H4	119.9
C15—C16—H16	119.7	C5—C4—H4	119.9
C17—C16—H16	119.7	C2—C3—C4	120.8 (3)
C10—C9—C7	123.1 (2)	C2—C3—H3	119.6
C10—C9—H9	118.5	C4—C3—H3	119.6
C7—C9—H9	118.5
C14—N13—C10—C9	−178.4 (2)	N13—C14—C19—C18	179.9 (2)
C14—N13—C10—S11	3.3 (3)	C6—C1—C2—C3	0.0 (4)
C12—S11—C10—N13	173.40 (17)	Cl20—C1—C2—C3	177.2 (2)
C12—S11—C10—C9	−4.9 (2)	C10—C9—C7—O8	−2.6 (3)
C10—N13—C14—C15	−137.6 (2)	C10—C9—C7—C6	172.84 (19)
C10—N13—C14—C19	44.6 (3)	C1—C6—C7—O8	−135.6 (2)
C19—C14—C15—C16	−1.3 (3)	C5—C6—C7—O8	44.8 (3)
N13—C14—C15—C16	−179.2 (2)	C1—C6—C7—C9	48.6 (3)
C2—C1—C6—C5	0.8 (3)	C5—C6—C7—C9	−131.0 (2)
Cl20—C1—C6—C5	−176.24 (18)	C19—C18—C17—C16	−0.4 (4)
C2—C1—C6—C7	−178.7 (2)	C15—C16—C17—C18	1.2 (4)
Cl20—C1—C6—C7	4.2 (3)	C1—C6—C5—C4	−1.2 (4)
C14—C15—C16—C17	−0.4 (4)	C7—C6—C5—C4	178.4 (2)
N13—C10—C9—C7	−0.7 (3)	C6—C5—C4—C3	0.9 (4)
S11—C10—C9—C7	177.57 (16)	C1—C2—C3—C4	−0.4 (4)
C17—C18—C19—C14	−1.3 (4)	C5—C4—C3—C2	0.0 (5)
C15—C14—C19—C18	2.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···O8	0.86	1.92	2.627 (2)	139
C12—H12A···O8^i	0.96	2.35	3.237 (3)	153
C15—H15···O8^ii	0.93	2.55	3.475 (3)	176

Symmetry codes: (i) x+1/2, −y+1, −z+1/2; (ii) −x+1, −y+1, −z.