1-[3-(2,4-Dichloro-5-fluoro­phen­yl)-5-(3-methyl-2-thien­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Anuradha, N.; Thiruvalluvar, A.; Mahalinga, M.; Butcher, R.J.

doi:10.1107/S1600536808033837

1-[3-(2,4-Dichloro-5-fluorophenyl)-5-(3-methyl-2-thienyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

N. Anuradha, A. Thiruvalluvar, M. Mahalinga and R. J. Butcher

In the title molecule, C₁₆H₁₃Cl₂FN₂OS, the dihedral angle between the thiophene and benzene rings is 80.34 (12)°. The pyrazoline ring is in an envelope conformation, and the plane through the four coplanar atoms makes dihedral angles of 85.13 (9) and 6.89 (10)° with the thiophene and benzene rings, respectively. The C and O atoms of the acetyl group are nearly coplanar with the attached pyrazoline ring. In the crystal structure, inversion dimers arise from pairs of intermolecular C—H

O hydrogen bonds. A short intermolecular Cl

S contact of 3.4250 (13) Å is also found.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808033837/wn2286sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808033837/wn2286Isup2.hkl Contains datablock I

CCDC reference: 709391

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R factor = 0.051
wR factor = 0.179
Data-to-parameter ratio = 25.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.786     1.000
            Tmin(prime) and Tmax expected:      0.755     0.831
            RR(prime) =      0.866
            Please check that your absorption correction is appropriate.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4    ..  S21     ..       3.42 Ang.
PLAT061_ALERT_4_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.83

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.831
            Tmax scaled      0.831 Tmin scaled      0.654
PLAT793_ALERT_4_G The Model has Chirality at C5      (Verify) ....          S

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

   0 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
   2 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

Comment top

A great deal of attention has been paid to the synthesis and structural aspects of pyrazolines, as witnessed by continued activity in this area (Thiruvalluvar et al., 2007).

In the title molecule, C₁₆H₁₃Cl₂FN₂OS, Fig.1., the dihedral angle between the thiophene and benzene rings is 80.34 (12)°. The pyrazoline ring is in an envelope conformation and the plane through the four coplanar atoms makes dihedral angles of 85.13 (9)° and 6.89 (10)° with the thiophene and benzene rings, respectively. The acetyl group, except for the hydrogen atoms, is nearly coplanar with the attached pyrazoline ring. An intermolecular C2—H2A···O1(-1 - x, 1 - y, -z) hydrogen bond is found in the crystal structure (Table 1). Further, a short intermolecular Cl4···S21(1-x,1-y,1-z) contact of 3.4250 (13) Å is also found in the crystal structure.

Related literature top

For a related crystal structure, see: Thiruvalluvar et al. (2007).

Experimental top

A mixture of 1-(2,4-dichloro-5-fluorophenyl)-3-(3-methylthien-2-yl) prop-2-en-1-one (5 g, 0.016 mol) and a molar equivalent of hydrazine hydrate (80%) in glacial acetic acid (25 ml) was heated on a water bath at 363–365 K for 5–6 h. The reaction mass was then poured into ice-cold water. The solid obtained was filtered, washed with water, dried and crystallized from methanol to yield the title compound. Yield 5.5 g (93.5%).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

1-[3-(2,4-Dichloro-5-fluorophenyl)-5-(3-methyl-2-thienyl)-4,5-dihydro-1H- pyrazol-1-yl]ethanone top

Crystal data top

C₁₆H₁₃Cl₂FN₂OS	Z = 2
M_r = 371.25	F(000) = 380
Triclinic, P1	D_x = 1.478 Mg m⁻³
Hall symbol: -P 1	Melting point: 369.5 K
a = 7.2240 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8642 (4) Å	Cell parameters from 4639 reflections
c = 14.0518 (9) Å	θ = 4.6–32.4°
α = 100.794 (5)°	µ = 0.53 mm⁻¹
β = 103.307 (6)°	T = 295 K
γ = 101.003 (5)°	Chunk, pale-yellow
V = 833.99 (10) Å³	0.52 × 0.43 × 0.35 mm

Data collection top

Oxford Diffraction R Gemini diffractometer	5445 independent reflections
Radiation source: fine-focus sealed tube	3028 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.5°, θ_min = 4.6°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −13→13
T_min = 0.786, T_max = 1.000	l = −21→21
12358 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.083P)² + 0.1183P] where P = (F_o² + 2F_c²)/3
5445 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₆H₁₃Cl₂FN₂OS	γ = 101.003 (5)°
M_r = 371.25	V = 833.99 (10) Å³
Triclinic, P1	Z = 2
a = 7.2240 (5) Å	Mo Kα radiation
b = 8.8642 (4) Å	µ = 0.53 mm⁻¹
c = 14.0518 (9) Å	T = 295 K
α = 100.794 (5)°	0.52 × 0.43 × 0.35 mm
β = 103.307 (6)°

Data collection top

Oxford Diffraction R Gemini diffractometer	5445 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	3028 reflections with I > 2σ(I)
T_min = 0.786, T_max = 1.000	R_int = 0.020
12358 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.12	Δρ_max = 0.32 e Å⁻³
5445 reflections	Δρ_min = −0.39 e Å⁻³
210 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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

	x	y	z	U_iso*/U_eq
Cl2	0.31301 (12)	0.93549 (8)	0.58594 (5)	0.0696 (3)
Cl4	0.45313 (12)	0.40815 (13)	0.68787 (6)	0.0875 (4)
S21	0.33962 (10)	0.82555 (8)	0.17261 (5)	0.0572 (2)
F5	0.2322 (3)	0.25555 (19)	0.47920 (15)	0.0820 (7)
O1	−0.2572 (3)	0.7121 (2)	0.06719 (14)	0.0721 (7)
N1	−0.0630 (3)	0.6973 (2)	0.21112 (13)	0.0432 (5)
N2	0.0012 (3)	0.6131 (2)	0.28019 (13)	0.0388 (5)
C1	−0.1967 (4)	0.6281 (3)	0.12037 (17)	0.0499 (7)
C2	−0.2599 (5)	0.4503 (3)	0.0905 (2)	0.0753 (10)
C3	0.1042 (3)	0.7120 (2)	0.36402 (15)	0.0352 (6)
C4	0.1162 (4)	0.8829 (3)	0.36061 (16)	0.0460 (7)
C5	0.0216 (3)	0.8696 (2)	0.24839 (16)	0.0434 (7)
C11	0.1899 (3)	0.6464 (3)	0.44812 (15)	0.0383 (6)
C12	0.2871 (3)	0.7332 (3)	0.54694 (16)	0.0464 (7)
C13	0.3677 (3)	0.6604 (4)	0.62105 (18)	0.0574 (9)
C14	0.3507 (4)	0.5009 (4)	0.5990 (2)	0.0574 (9)
C15	0.2522 (4)	0.4140 (3)	0.5020 (2)	0.0533 (8)
C16	0.1750 (3)	0.4835 (3)	0.42821 (18)	0.0457 (7)
C22	0.1646 (3)	0.9275 (3)	0.19146 (16)	0.0429 (6)
C23	0.1824 (4)	1.0568 (3)	0.15275 (18)	0.0514 (8)
C24	0.3412 (4)	1.0737 (3)	0.10905 (19)	0.0629 (9)
C25	0.4390 (4)	0.9588 (4)	0.1136 (2)	0.0634 (10)
C26	0.0455 (5)	1.1637 (3)	0.1527 (3)	0.0800 (11)
H2A	−0.39392	0.41733	0.05015	0.1130*
H2B	−0.24825	0.41020	0.14997	0.1130*
H2C	−0.17792	0.40987	0.05240	0.1130*
H4A	0.25124	0.94454	0.38196	0.0552*
H4B	0.04343	0.93070	0.40277	0.0552*
H5	−0.08333	0.92575	0.24149	0.0520*
H13	0.43338	0.72114	0.68588	0.0688*
H16	0.11130	0.42108	0.36356	0.0549*
H24	0.37514	1.15693	0.07973	0.0755*
H25	0.54602	0.95296	0.08813	0.0761*
H26A	−0.01973	1.15300	0.20427	0.1200*
H26B	−0.05021	1.13543	0.08824	0.1200*
H26C	0.11838	1.27147	0.16557	0.1200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.0784 (5)	0.0659 (4)	0.0470 (4)	0.0100 (3)	0.0044 (3)	−0.0045 (3)
Cl4	0.0679 (5)	0.1559 (8)	0.0819 (5)	0.0599 (5)	0.0340 (4)	0.0827 (5)
S21	0.0645 (4)	0.0652 (4)	0.0544 (4)	0.0279 (3)	0.0223 (3)	0.0251 (3)
F5	0.0976 (14)	0.0656 (10)	0.1059 (14)	0.0393 (10)	0.0337 (11)	0.0495 (10)
O1	0.0727 (13)	0.0737 (12)	0.0585 (11)	0.0147 (10)	−0.0122 (9)	0.0292 (10)
N1	0.0460 (10)	0.0385 (9)	0.0402 (9)	0.0047 (8)	0.0017 (8)	0.0163 (7)
N2	0.0357 (9)	0.0400 (9)	0.0378 (9)	0.0061 (7)	0.0032 (7)	0.0146 (7)
C1	0.0470 (13)	0.0536 (13)	0.0429 (12)	0.0087 (10)	0.0013 (10)	0.0142 (10)
C2	0.082 (2)	0.0553 (15)	0.0583 (16)	0.0023 (14)	−0.0197 (14)	0.0040 (13)
C3	0.0335 (10)	0.0376 (10)	0.0371 (10)	0.0093 (8)	0.0117 (8)	0.0123 (8)
C4	0.0565 (14)	0.0401 (11)	0.0394 (11)	0.0083 (10)	0.0135 (10)	0.0083 (9)
C5	0.0493 (12)	0.0368 (10)	0.0445 (12)	0.0116 (9)	0.0088 (9)	0.0150 (9)
C11	0.0345 (10)	0.0487 (11)	0.0353 (10)	0.0117 (9)	0.0116 (8)	0.0147 (9)
C12	0.0371 (11)	0.0611 (14)	0.0386 (11)	0.0083 (10)	0.0095 (9)	0.0115 (10)
C13	0.0408 (12)	0.095 (2)	0.0397 (12)	0.0185 (13)	0.0095 (10)	0.0242 (13)
C14	0.0424 (12)	0.093 (2)	0.0593 (15)	0.0309 (13)	0.0232 (11)	0.0465 (14)
C15	0.0467 (13)	0.0635 (15)	0.0669 (16)	0.0231 (11)	0.0255 (11)	0.0354 (12)
C16	0.0435 (12)	0.0524 (12)	0.0468 (12)	0.0146 (10)	0.0147 (9)	0.0195 (10)
C22	0.0489 (12)	0.0388 (10)	0.0373 (10)	0.0064 (9)	0.0049 (9)	0.0133 (8)
C23	0.0632 (15)	0.0427 (12)	0.0436 (12)	0.0093 (10)	0.0059 (11)	0.0136 (10)
C24	0.0743 (18)	0.0605 (15)	0.0468 (14)	−0.0042 (13)	0.0134 (12)	0.0209 (12)
C25	0.0626 (17)	0.0799 (19)	0.0507 (14)	0.0115 (14)	0.0215 (12)	0.0215 (13)
C26	0.100 (2)	0.0523 (15)	0.085 (2)	0.0327 (16)	0.0071 (18)	0.0184 (15)

Geometric parameters (Å, º) top

Cl2—C12	1.734 (3)	C14—C15	1.382 (4)
Cl4—C14	1.725 (3)	C15—C16	1.367 (4)
S21—C22	1.728 (2)	C22—C23	1.355 (4)
S21—C25	1.707 (3)	C23—C24	1.417 (4)
F5—C15	1.352 (3)	C23—C26	1.495 (4)
O1—C1	1.219 (3)	C24—C25	1.349 (4)
N1—N2	1.382 (3)	C2—H2A	0.9600
N1—C1	1.360 (3)	C2—H2B	0.9600
N1—C5	1.476 (3)	C2—H2C	0.9600
N2—C3	1.293 (3)	C4—H4A	0.9700
C1—C2	1.503 (4)	C4—H4B	0.9700
C3—C4	1.511 (3)	C5—H5	0.9800
C3—C11	1.475 (3)	C13—H13	0.9300
C4—C5	1.540 (3)	C16—H16	0.9300
C5—C22	1.517 (3)	C24—H24	0.9300
C11—C12	1.399 (3)	C25—H25	0.9300
C11—C16	1.397 (4)	C26—H26A	0.9600
C12—C13	1.399 (4)	C26—H26B	0.9600
C13—C14	1.365 (5)	C26—H26C	0.9600

Cl2···C4	3.064 (2)	C11···C15ⁱⁱ	3.391 (4)
Cl2···S21ⁱ	3.6953 (10)	C14···C15ⁱⁱⁱ	3.502 (4)
Cl4···N1ⁱⁱ	3.488 (2)	C14···C16ⁱⁱⁱ	3.514 (4)
Cl4···N2ⁱⁱ	3.389 (2)	C15···C14ⁱⁱⁱ	3.502 (4)
Cl4···C11ⁱⁱⁱ	3.596 (2)	C15···C11ⁱⁱ	3.391 (4)
Cl4···C16ⁱⁱⁱ	3.524 (3)	C16···Cl4ⁱⁱⁱ	3.524 (3)
Cl4···F5	2.917 (2)	C16···C14ⁱⁱⁱ	3.514 (4)
Cl4···S21ⁱⁱⁱ	3.4250 (13)	C16···C16ⁱⁱ	3.600 (3)
Cl4···C1ⁱⁱ	3.632 (3)	C22···O1	3.172 (3)
Cl2···H4A	2.8200	C24···O1^vi	3.408 (3)
Cl2···H4B	2.8400	C5···H26A	2.7500
Cl2···H4Aⁱ	3.0200	C24···H13ⁱ	3.0000
Cl2···H4B^iv	3.0600	C24···H25^x	3.0400
S21···N1	3.121 (2)	C24···H26B^vi	3.0700
S21···C3	3.689 (2)	C25···H25^x	3.1000
S21···Cl2ⁱ	3.6953 (10)	C26···H5	2.7600
S21···Cl4ⁱⁱⁱ	3.4250 (13)	H2A···O1^viii	2.5800
S21···H4A	3.1800	H2B···N2	2.4200
F5···Cl4	2.917 (2)	H4A···Cl2	2.8200
F5···C4^v	3.260 (3)	H4A···S21	3.1800
F5···H4B^v	2.8200	H4A···Cl2ⁱ	3.0200
O1···C22	3.172 (3)	H4B···Cl2	2.8400
O1···C24^vi	3.408 (3)	H4B···F5^ix	2.8200
O1···H5	2.6600	H4B···Cl2^iv	3.0600
O1···H25^vii	2.7900	H5···O1	2.6600
O1···H2A^viii	2.5800	H5···C26	2.7600
O1···H24^vi	2.6100	H5···H26A	2.1700
N1···S21	3.121 (2)	H13···C24ⁱ	3.0000
N1···Cl4ⁱⁱ	3.488 (2)	H16···N2	2.4000
N2···Cl4ⁱⁱ	3.389 (2)	H24···O1^vi	2.6100
N2···H2B	2.4200	H25···O1^xi	2.7900
N2···H16	2.4000	H25···C24^x	3.0400
C1···Cl4ⁱⁱ	3.632 (3)	H25···C25^x	3.1000
C3···S21	3.689 (2)	H26A···C5	2.7500
C4···Cl2	3.064 (2)	H26A···H5	2.1700
C4···F5^ix	3.260 (3)	H26B···C24^vi	3.0700
C11···Cl4ⁱⁱⁱ	3.596 (2)

C22—S21—C25	91.98 (14)	C22—C23—C26	123.8 (3)
N2—N1—C1	123.08 (19)	C24—C23—C26	124.6 (3)
N2—N1—C5	112.89 (16)	C23—C24—C25	114.3 (3)
C1—N1—C5	123.97 (19)	S21—C25—C24	110.8 (2)
N1—N2—C3	108.80 (17)	C1—C2—H2A	109.00
O1—C1—N1	118.9 (2)	C1—C2—H2B	109.00
O1—C1—C2	123.5 (2)	C1—C2—H2C	109.00
N1—C1—C2	117.6 (2)	H2A—C2—H2B	109.00
N2—C3—C4	113.05 (18)	H2A—C2—H2C	110.00
N2—C3—C11	117.69 (18)	H2B—C2—H2C	109.00
C4—C3—C11	129.25 (19)	C3—C4—H4A	111.00
C3—C4—C5	102.60 (17)	C3—C4—H4B	111.00
N1—C5—C4	101.26 (16)	C5—C4—H4A	111.00
N1—C5—C22	110.98 (18)	C5—C4—H4B	111.00
C4—C5—C22	114.48 (19)	H4A—C4—H4B	109.00
C3—C11—C12	125.8 (2)	N1—C5—H5	110.00
C3—C11—C16	117.75 (19)	C4—C5—H5	110.00
C12—C11—C16	116.5 (2)	C22—C5—H5	110.00
Cl2—C12—C11	122.69 (19)	C12—C13—H13	120.00
Cl2—C12—C13	115.80 (19)	C14—C13—H13	120.00
C11—C12—C13	121.5 (2)	C11—C16—H16	119.00
C12—C13—C14	120.5 (2)	C15—C16—H16	119.00
Cl4—C14—C13	121.7 (2)	C23—C24—H24	123.00
Cl4—C14—C15	120.0 (3)	C25—C24—H24	123.00
C13—C14—C15	118.3 (3)	S21—C25—H25	125.00
F5—C15—C14	119.0 (3)	C24—C25—H25	125.00
F5—C15—C16	119.0 (2)	C23—C26—H26A	110.00
C14—C15—C16	122.0 (3)	C23—C26—H26B	110.00
C11—C16—C15	121.2 (2)	C23—C26—H26C	109.00
S21—C22—C5	119.58 (18)	H26A—C26—H26B	109.00
S21—C22—C23	111.36 (19)	H26A—C26—H26C	109.00
C5—C22—C23	129.0 (2)	H26B—C26—H26C	109.00
C22—C23—C24	111.6 (2)

C25—S21—C22—C5	−177.60 (19)	C4—C5—C22—S21	66.8 (2)
C25—S21—C22—C23	0.6 (2)	C4—C5—C22—C23	−111.1 (3)
C22—S21—C25—C24	−0.2 (2)	C3—C11—C12—Cl2	2.4 (3)
C1—N1—N2—C3	−170.7 (2)	C3—C11—C12—C13	−178.4 (2)
C5—N1—N2—C3	6.6 (3)	C16—C11—C12—Cl2	−178.11 (18)
N2—N1—C1—O1	174.2 (2)	C16—C11—C12—C13	1.1 (3)
C5—N1—C1—O1	−2.8 (4)	C3—C11—C16—C15	179.5 (2)
N2—N1—C1—C2	−6.6 (4)	C12—C11—C16—C15	−0.1 (4)
C5—N1—C1—C2	176.4 (2)	Cl2—C12—C13—C14	178.2 (2)
N2—N1—C5—C4	−11.3 (3)	C11—C12—C13—C14	−1.0 (4)
C1—N1—C5—C4	166.0 (2)	C12—C13—C14—Cl4	178.5 (2)
N2—N1—C5—C22	110.7 (2)	C12—C13—C14—C15	0.0 (4)
C1—N1—C5—C22	−72.1 (3)	Cl4—C14—C15—F5	2.2 (4)
N1—N2—C3—C11	−179.1 (2)	Cl4—C14—C15—C16	−177.6 (2)
N1—N2—C3—C4	1.6 (3)	C13—C14—C15—F5	−179.3 (3)
N2—C3—C4—C5	−8.4 (3)	C13—C14—C15—C16	1.0 (4)
C4—C3—C11—C16	−173.1 (2)	F5—C15—C16—C11	179.3 (2)
N2—C3—C11—C12	−172.7 (2)	C14—C15—C16—C11	−1.0 (4)
N2—C3—C11—C16	7.8 (3)	S21—C22—C23—C24	−0.9 (3)
C11—C3—C4—C5	172.4 (2)	S21—C22—C23—C26	176.7 (2)
C4—C3—C11—C12	6.4 (4)	C5—C22—C23—C24	177.1 (2)
C3—C4—C5—N1	10.9 (2)	C5—C22—C23—C26	−5.3 (4)
C3—C4—C5—C22	−108.6 (2)	C22—C23—C24—C25	0.8 (3)
N1—C5—C22—S21	−47.0 (2)	C26—C23—C24—C25	−176.8 (3)
N1—C5—C22—C23	135.1 (2)	C23—C24—C25—S21	−0.3 (3)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+2, −z+1; (v) x, y−1, z; (vi) −x, −y+2, −z; (vii) x−1, y, z; (viii) −x−1, −y+1, −z; (ix) x, y+1, z; (x) −x+1, −y+2, −z; (xi) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1^viii	0.96	2.58	3.533 (4)	171

Symmetry code: (viii) −x−1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃Cl₂FN₂OS
M_r	371.25
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.2240 (5), 8.8642 (4), 14.0518 (9)
α, β, γ (°)	100.794 (5), 103.307 (6), 101.003 (5)
V (Å³)	833.99 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.52 × 0.43 × 0.35

Data collection
Diffractometer	Oxford Diffraction R Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.786, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12358, 5445, 3028
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.755

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.179, 1.12
No. of reflections	5445
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.39

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).