Crystal structure of ethyl 4-(2-chloro­phen­yl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzo­thia­zole-3-carboxyl­ate

Kumar, B.; Kour, M.; Paul, S.; Kant, R.; Gupta, V.K.

doi:10.1107/S2056989015014905

organic compounds

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Volume 71| Part 9| September 2015| Page o669

https://doi.org/10.1107/S2056989015014905

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Crystal structure of ethyl 4-(2-chlorophenyl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazole-3-carboxylate

Balbir Kumar,^a Manmeet Kour,^b Satya Paul,^b Rajni Kant ^a and Vivek K. Gupta ^a ^*

^aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Chemistry, University of Jammu, Jammu Tawi 180 006, India
^*Correspondence e-mail: vivek_gupta2k2@hotmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 1 August 2015; accepted 9 August 2015; online 22 August 2015)

In the title compound, C₂₀H₁₇ClN₂O₂S, the dihedral angle between the planes of the benzothiazole fused ring system (r.m.s. deviation = 0.024 Å) and the chlorobenzene ring is 89.62 (12)°. The ester C—O—C—C side chain has an anti orientation [torsion angle = −155.2 (3)°]. In the crystal, weak aromatic π–π stacking interactions are observed between the phenyl and pyrimidine rings [centroid–centroid seperation = 3.666 (2) Å].

Keywords: crystal structure; pyrimido[2,1-b][1,3]benzothiazole; ester; biological activity.

CCDC reference: 1406433

1. Related literature

For biological activities of benzothiazoles, see: Landreau et al. (2002 ); Russo et al. (1985 ). For a related structure, see: Sankar et al. (2015 ).

2. Experimental

2.1. Crystal data

C₂₀H₁₇ClN₂O₂S
M_r = 384.87
Triclinic, $[P \overline 1]$
a = 8.9049 (8) Å
b = 8.9275 (10) Å
c = 12.3564 (11) Å
α = 88.434 (8)°
β = 83.536 (7)°
γ = 66.201 (10)°
V = 892.90 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

2.2. Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.880, T_max = 1.000
6440 measured reflections
3477 independent reflections
2275 reflections with I > 2σ(I)
R_int = 0.033

2.3. Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.142
S = 1.03
3477 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1406433

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015014905/hb7475sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014905/hb7475Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015014905/hb7475Isup3.cml

checkCIF report

Related literature top

For the biological activities of benzothiazoles, see: Landreau et al. (2002); Russo et al. (1985). For a related structure, see: Sankar et al. (2015).

Experimental top

To a mixture of ethylacetoacetate (1.0 mmol, 0.13 g), 2-chlorobenzadehyde (1.0 mmol, 0.14 g) and 2-aminobenzothiazole (1.0 mmol, 0.152 g) in a round bottom flask (25 ml), C/TiO₂·SO₃·SbCl₂ (0.1 g) was added and the reaction mixture was heated at 363 K under solvent-free conditions for 1 h. Hot ethanol (2 × 5 ml) was added to the reaction mixture and the catalyst was separated by simple filteration. Removal of the solvent under reduced pressure afforded the product, which was further crystallized from ethanol as yellow crystals (Yield: 88%).

Structure description top

For the biological activities of benzothiazoles, see: Landreau et al. (2002); Russo et al. (1985). For a related structure, see: Sankar et al. (2015).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the molecule with displacement ellipsoids drawn at the 40% probability level.
	Fig. 2. The packing arrangement of molecules viewed down the a axis.

Ethyl 4-(2-chlorophenyl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazole- 3-carboxylate top

Crystal data top

C₂₀H₁₇ClN₂O₂S	Z = 2
M_r = 384.87	F(000) = 400
Triclinic, P1	D_x = 1.431 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9049 (8) Å	Cell parameters from 1737 reflections
b = 8.9275 (10) Å	θ = 4.1–27.4°
c = 12.3564 (11) Å	µ = 0.35 mm⁻¹
α = 88.434 (8)°	T = 293 K
β = 83.536 (7)°	Block, colourless
γ = 66.201 (10)°	0.30 × 0.20 × 0.20 mm
V = 892.90 (15) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3477 independent reflections
Radiation source: fine-focus sealed tube	2275 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.9°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −10→10
T_min = 0.880, T_max = 1.000	l = −9→15
6440 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0556P)² + 0.235P] where P = (F_o² + 2F_c²)/3
3477 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₁₇ClN₂O₂S	γ = 66.201 (10)°
M_r = 384.87	V = 892.90 (15) Å³
Triclinic, P1	Z = 2
a = 8.9049 (8) Å	Mo Kα radiation
b = 8.9275 (10) Å	µ = 0.35 mm⁻¹
c = 12.3564 (11) Å	T = 293 K
α = 88.434 (8)°	0.30 × 0.20 × 0.20 mm
β = 83.536 (7)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3477 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2275 reflections with I > 2σ(I)
T_min = 0.880, T_max = 1.000	R_int = 0.033
6440 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	Δρ_max = 0.64 e Å⁻³
3477 reflections	Δρ_min = −0.35 e Å⁻³
237 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S7	0.83804 (10)	0.01946 (11)	0.38623 (8)	0.0592 (3)
Cl1	0.02890 (10)	0.33670 (11)	0.39074 (8)	0.0648 (3)
N9	0.5363 (3)	0.0924 (2)	0.35456 (18)	0.0370 (6)
C25	0.1519 (4)	0.3941 (3)	0.2942 (2)	0.0431 (7)
C12	0.4497 (3)	−0.0172 (3)	0.2052 (2)	0.0368 (7)
O16	0.1721 (3)	0.0825 (2)	0.17927 (17)	0.0531 (6)
N10	0.7388 (3)	−0.0979 (3)	0.2270 (2)	0.0503 (7)
C21	0.4011 (4)	0.3408 (3)	0.1786 (2)	0.0445 (7)
H21	0.5087	0.2715	0.1531	0.053*
C8	0.6924 (3)	−0.0008 (3)	0.3117 (2)	0.0427 (7)
C20	0.3121 (3)	0.2857 (3)	0.2573 (2)	0.0345 (6)
C15	0.3219 (4)	−0.0328 (3)	0.1475 (2)	0.0446 (7)
O19	0.3434 (3)	−0.1335 (3)	0.0766 (2)	0.0719 (7)
C13	0.3919 (3)	0.1118 (3)	0.2977 (2)	0.0341 (6)
H13	0.3110	0.0911	0.3495	0.041*
C1	0.5264 (3)	0.1829 (3)	0.4491 (2)	0.0370 (7)
C11	0.6124 (4)	−0.1115 (3)	0.1764 (2)	0.0443 (7)
C3	0.4058 (4)	0.3661 (4)	0.6003 (3)	0.0553 (9)
H3	0.3125	0.4372	0.6429	0.066*
C24	0.0834 (4)	0.5496 (4)	0.2540 (3)	0.0612 (10)
H24	−0.0238	0.6201	0.2795	0.073*
C2	0.3873 (4)	0.2860 (4)	0.5114 (2)	0.0473 (8)
H2	0.2829	0.3019	0.4944	0.057*
C17	0.0396 (4)	0.0912 (4)	0.1179 (3)	0.0608 (9)
H17A	−0.0047	0.0128	0.1455	0.073*
H17B	0.0815	0.0642	0.0419	0.073*
C6	0.6823 (4)	0.1580 (3)	0.4765 (2)	0.0439 (7)
C14	0.6786 (4)	−0.2416 (4)	0.0879 (3)	0.0640 (10)
H14A	0.6468	−0.3300	0.1087	0.096*
H14B	0.7969	−0.2819	0.0772	0.096*
H14C	0.6343	−0.1959	0.0214	0.096*
C5	0.6991 (4)	0.2383 (4)	0.5662 (3)	0.0561 (9)
H5	0.8031	0.2214	0.5845	0.067*
C4	0.5604 (4)	0.3422 (4)	0.6264 (3)	0.0601 (9)
H4	0.5697	0.3978	0.6861	0.072*
C23	0.1744 (5)	0.5998 (4)	0.1761 (3)	0.0675 (11)
H23	0.1283	0.7051	0.1491	0.081*
C18	−0.0923 (5)	0.2586 (5)	0.1279 (4)	0.0812 (12)
H18A	−0.1419	0.2802	0.2021	0.122*
H18B	−0.1747	0.2677	0.0813	0.122*
H18C	−0.0457	0.3365	0.1069	0.122*
C22	0.3327 (5)	0.4969 (4)	0.1373 (3)	0.0594 (10)
H22	0.3932	0.5316	0.0839	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S7	0.0328 (4)	0.0641 (5)	0.0699 (6)	−0.0056 (4)	−0.0153 (4)	−0.0055 (5)
Cl1	0.0374 (5)	0.0726 (6)	0.0751 (6)	−0.0129 (4)	−0.0018 (4)	−0.0116 (5)
N9	0.0318 (13)	0.0316 (11)	0.0424 (14)	−0.0058 (10)	−0.0106 (11)	0.0003 (10)
C25	0.0382 (16)	0.0343 (14)	0.0534 (19)	−0.0077 (13)	−0.0169 (15)	−0.0053 (13)
C12	0.0402 (16)	0.0244 (12)	0.0425 (16)	−0.0089 (12)	−0.0075 (14)	−0.0002 (12)
O16	0.0401 (12)	0.0549 (12)	0.0632 (14)	−0.0144 (10)	−0.0165 (11)	−0.0126 (11)
N10	0.0361 (14)	0.0421 (13)	0.0579 (17)	−0.0002 (11)	−0.0040 (13)	−0.0080 (13)
C21	0.0514 (19)	0.0383 (15)	0.0456 (18)	−0.0177 (14)	−0.0141 (16)	−0.0004 (13)
C8	0.0324 (16)	0.0349 (14)	0.0517 (18)	−0.0028 (12)	−0.0107 (14)	0.0046 (14)
C20	0.0341 (15)	0.0295 (13)	0.0395 (16)	−0.0100 (12)	−0.0131 (13)	−0.0019 (12)
C15	0.0512 (19)	0.0349 (15)	0.0499 (18)	−0.0189 (14)	−0.0085 (16)	0.0017 (14)
O19	0.0711 (17)	0.0584 (14)	0.0851 (18)	−0.0210 (13)	−0.0161 (15)	−0.0285 (13)
C13	0.0299 (14)	0.0297 (13)	0.0421 (16)	−0.0097 (11)	−0.0104 (13)	0.0026 (12)
C1	0.0351 (16)	0.0344 (14)	0.0413 (16)	−0.0112 (12)	−0.0152 (13)	0.0058 (13)
C11	0.0492 (18)	0.0291 (14)	0.0487 (18)	−0.0092 (13)	−0.0068 (15)	−0.0011 (13)
C3	0.050 (2)	0.0590 (19)	0.0467 (19)	−0.0105 (16)	−0.0080 (16)	−0.0088 (16)
C24	0.053 (2)	0.0373 (17)	0.081 (3)	0.0000 (16)	−0.028 (2)	−0.0075 (17)
C2	0.0403 (17)	0.0554 (18)	0.0430 (17)	−0.0143 (15)	−0.0111 (15)	−0.0004 (15)
C17	0.052 (2)	0.068 (2)	0.074 (2)	−0.0304 (18)	−0.0224 (19)	−0.0030 (18)
C6	0.0400 (17)	0.0410 (15)	0.0484 (18)	−0.0121 (13)	−0.0129 (15)	0.0037 (14)
C14	0.058 (2)	0.0497 (18)	0.068 (2)	−0.0050 (17)	−0.0011 (19)	−0.0180 (18)
C5	0.048 (2)	0.064 (2)	0.060 (2)	−0.0208 (17)	−0.0246 (18)	0.0024 (18)
C4	0.065 (2)	0.066 (2)	0.053 (2)	−0.0261 (19)	−0.0207 (19)	−0.0087 (18)
C23	0.087 (3)	0.0312 (16)	0.079 (3)	−0.0107 (19)	−0.042 (2)	0.0046 (18)
C18	0.064 (3)	0.082 (3)	0.098 (3)	−0.022 (2)	−0.043 (2)	0.008 (2)
C22	0.092 (3)	0.0491 (19)	0.051 (2)	−0.039 (2)	−0.021 (2)	0.0095 (16)

Geometric parameters (Å, º) top

S7—C8	1.741 (3)	C11—C14	1.505 (4)
S7—C6	1.744 (3)	C3—C4	1.379 (4)
Cl1—C25	1.735 (3)	C3—C2	1.388 (4)
N9—C8	1.353 (3)	C3—H3	0.9300
N9—C1	1.413 (3)	C24—C23	1.370 (5)
N9—C13	1.481 (3)	C24—H24	0.9300
C25—C24	1.376 (4)	C2—H2	0.9300
C25—C20	1.394 (4)	C17—C18	1.479 (5)
C12—C11	1.360 (4)	C17—H17A	0.9700
C12—C15	1.462 (4)	C17—H17B	0.9700
C12—C13	1.536 (3)	C6—C5	1.390 (4)
O16—C15	1.338 (3)	C14—H14A	0.9600
O16—C17	1.448 (3)	C14—H14B	0.9600
N10—C8	1.296 (4)	C14—H14C	0.9600
N10—C11	1.394 (4)	C5—C4	1.359 (4)
C21—C22	1.385 (4)	C5—H5	0.9300
C21—C20	1.389 (4)	C4—H4	0.9300
C21—H21	0.9300	C23—C22	1.374 (5)
C20—C13	1.521 (3)	C23—H23	0.9300
C15—O19	1.216 (3)	C18—H18A	0.9600
C13—H13	0.9800	C18—H18B	0.9600
C1—C2	1.370 (4)	C18—H18C	0.9600
C1—C6	1.394 (4)	C22—H22	0.9300

C8—S7—C6	91.01 (14)	C23—C24—C25	119.5 (3)
C8—N9—C1	114.1 (2)	C23—C24—H24	120.2
C8—N9—C13	121.6 (2)	C25—C24—H24	120.2
C1—N9—C13	123.8 (2)	C1—C2—C3	118.5 (3)
C24—C25—C20	121.5 (3)	C1—C2—H2	120.7
C24—C25—Cl1	117.2 (3)	C3—C2—H2	120.7
C20—C25—Cl1	121.3 (2)	O16—C17—C18	109.4 (3)
C11—C12—C15	121.0 (2)	O16—C17—H17A	109.8
C11—C12—C13	121.9 (2)	C18—C17—H17A	109.8
C15—C12—C13	117.1 (2)	O16—C17—H17B	109.8
C15—O16—C17	116.6 (2)	C18—C17—H17B	109.8
C8—N10—C11	115.9 (2)	H17A—C17—H17B	108.2
C22—C21—C20	121.3 (3)	C5—C6—C1	120.7 (3)
C22—C21—H21	119.3	C5—C6—S7	128.0 (2)
C20—C21—H21	119.3	C1—C6—S7	111.2 (2)
N10—C8—N9	127.7 (3)	C11—C14—H14A	109.5
N10—C8—S7	120.5 (2)	C11—C14—H14B	109.5
N9—C8—S7	111.8 (2)	H14A—C14—H14B	109.5
C21—C20—C25	117.5 (3)	C11—C14—H14C	109.5
C21—C20—C13	119.1 (2)	H14A—C14—H14C	109.5
C25—C20—C13	123.4 (3)	H14B—C14—H14C	109.5
O19—C15—O16	121.7 (3)	C4—C5—C6	118.6 (3)
O19—C15—C12	126.3 (3)	C4—C5—H5	120.7
O16—C15—C12	112.0 (2)	C6—C5—H5	120.7
N9—C13—C20	110.1 (2)	C5—C4—C3	120.9 (3)
N9—C13—C12	108.4 (2)	C5—C4—H4	119.6
C20—C13—C12	112.7 (2)	C3—C4—H4	119.6
N9—C13—H13	108.5	C24—C23—C22	120.9 (3)
C20—C13—H13	108.5	C24—C23—H23	119.5
C12—C13—H13	108.5	C22—C23—H23	119.5
C2—C1—C6	120.2 (2)	C17—C18—H18A	109.5
C2—C1—N9	128.0 (2)	C17—C18—H18B	109.5
C6—C1—N9	111.9 (2)	H18A—C18—H18B	109.5
C12—C11—N10	123.1 (2)	C17—C18—H18C	109.5
C12—C11—C14	125.1 (3)	H18A—C18—H18C	109.5
N10—C11—C14	111.8 (3)	H18B—C18—H18C	109.5
C4—C3—C2	121.1 (3)	C23—C22—C21	119.2 (4)
C4—C3—H3	119.5	C23—C22—H22	120.4
C2—C3—H3	119.5	C21—C22—H22	120.4

C11—N10—C8—N9	−2.2 (5)	C15—C12—C13—C20	−65.5 (3)
C11—N10—C8—S7	176.9 (2)	C8—N9—C1—C2	−179.2 (3)
C1—N9—C8—N10	178.7 (3)	C13—N9—C1—C2	8.4 (4)
C13—N9—C8—N10	−8.7 (5)	C8—N9—C1—C6	1.1 (3)
C1—N9—C8—S7	−0.4 (3)	C13—N9—C1—C6	−171.3 (2)
C13—N9—C8—S7	172.18 (18)	C15—C12—C11—N10	178.2 (3)
C6—S7—C8—N10	−179.5 (3)	C13—C12—C11—N10	−0.7 (4)
C6—S7—C8—N9	−0.3 (2)	C15—C12—C11—C14	−2.0 (5)
C22—C21—C20—C25	−0.7 (4)	C13—C12—C11—C14	179.1 (3)
C22—C21—C20—C13	178.5 (2)	C8—N10—C11—C12	6.8 (4)
C24—C25—C20—C21	0.4 (4)	C8—N10—C11—C14	−173.1 (3)
Cl1—C25—C20—C21	178.98 (19)	C20—C25—C24—C23	−0.2 (4)
C24—C25—C20—C13	−178.9 (2)	Cl1—C25—C24—C23	−178.8 (2)
Cl1—C25—C20—C13	−0.3 (4)	C6—C1—C2—C3	1.1 (4)
C17—O16—C15—O19	−5.8 (4)	N9—C1—C2—C3	−178.6 (3)
C17—O16—C15—C12	172.5 (2)	C4—C3—C2—C1	−0.5 (5)
C11—C12—C15—O19	5.4 (5)	C15—O16—C17—C18	−155.2 (3)
C13—C12—C15—O19	−175.7 (3)	C2—C1—C6—C5	−0.8 (4)
C11—C12—C15—O16	−172.8 (3)	N9—C1—C6—C5	179.0 (3)
C13—C12—C15—O16	6.1 (4)	C2—C1—C6—S7	179.0 (2)
C8—N9—C13—C20	−110.7 (3)	N9—C1—C6—S7	−1.3 (3)
C1—N9—C13—C20	61.2 (3)	C8—S7—C6—C5	−179.4 (3)
C8—N9—C13—C12	12.9 (3)	C8—S7—C6—C1	0.9 (2)
C1—N9—C13—C12	−175.2 (2)	C1—C6—C5—C4	−0.2 (5)
C21—C20—C13—N9	64.4 (3)	S7—C6—C5—C4	−179.9 (3)
C25—C20—C13—N9	−116.4 (3)	C6—C5—C4—C3	0.8 (5)
C21—C20—C13—C12	−56.7 (3)	C2—C3—C4—C5	−0.5 (5)
C25—C20—C13—C12	122.5 (3)	C25—C24—C23—C22	0.3 (5)
C11—C12—C13—N9	−8.7 (4)	C24—C23—C22—C21	−0.6 (5)
C15—C12—C13—N9	172.4 (2)	C20—C21—C22—C23	0.9 (4)
C11—C12—C13—C20	113.4 (3)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇ClN₂O₂S
M_r	384.87
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.9049 (8), 8.9275 (10), 12.3564 (11)
α, β, γ (°)	88.434 (8), 83.536 (7), 66.201 (10)
V (Å³)	892.90 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.880, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6440, 3477, 2275
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.142, 1.03
No. of reflections	3477
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.35

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

Acknowledgements

RK acknowledges the Department of Science & Technology for single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.

References

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