(Z)-3-(2,4-Dichloro­benz­yl)-1,5-benzo­thia­zepin-4(5H)-one

Murugavel, S.; Manikandan, N.; Selvakumar, R.; Bakthadoss, M.

doi:10.1107/S1600536813007435

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o564

doi:10.1107/S1600536813007435

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(Z)-3-(2,4-Dichlorobenzyl)-1,5-benzothiazepin-4(5H)-one

S. Murugavel,^a ^* N. Manikandan,^b R. Selvakumar ^c and M. Bakthadoss ^c ‡

^aDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, ^bDepartment of Physics, Bharathidasan Engineering College, Nattrampalli, Vellore 635 854, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 16 March 2013; accepted 18 March 2013; online 23 March 2013)

In the title compound, C₁₆H₁₁Cl₂NOS, the seven-membered thiazepine ring adopts a distorted twist-boat conformation. The dihedral angle between the mean plane of the benzothiazepine ring system and the benzene ring is 78.6 (1)°. The molecular conformation is stabilized by a weak intramolecular C—H⋯Cl hydrogen bond, which generates an S(5) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds link inversion-related molecules into dimers, generating R₂²(8) ring motifs. The crystal packing also features alternating π–π interactions between benzothiazepine benzene rings [inter-centroid distance = 3.740 (3) Å] and dichlorobenzene rings [inter-centroid distance = 3.882 (3) Å] to consolidate a three-dimensional architecture.

Related literature

For background to the biology and related structures of thiazepin derivatives, see: Bakthadoss et al. (2013 ). For ring-puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₁Cl₂NOS
M_r = 336.22
Triclinic, $[P \overline 1]$
a = 7.879 (5) Å
b = 9.667 (5) Å
c = 9.979 (5) Å
α = 89.052 (5)°
β = 78.161 (4)°
γ = 83.647 (5)°
V = 739.3 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 293 K
0.24 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.871, T_max = 0.917
18415 measured reflections
5225 independent reflections
4013 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.123
S = 1.04
5225 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯Cl1	0.97	2.64	3.103 (3)	109
N1—H1A⋯O1ⁱ	0.86	2.10	2.873 (2)	149
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813007435/tk5208sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813007435/tk5208Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813007435/tk5208Isup3.cml

checkCIF report

Comment top

The background to the biology and related structures of thiazepin derivatives, has been described recently (Bakthadoss et al., 2013). In view of this biological importance, the crystal structure of the title compound has been carried out and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The seven membered thiazepine ring (N1/S1/C1/C2/C7/C8/C9) adopts distorted twist-boat conformation as indicated by puckering parameters (Cremer & Pople, 1975): QT = 0.8962 (12) Å, ϕ₂ = 353.2 (1)° and ϕ₃ = 358.9 (3)°. The atom O1 deviates by 0.667 (1) Å from the least-squares plane of the thiazepin ring. The dihedral angle between the benzothiazepin ring system and the benzene ring is 78.6 (1)°. The atoms Cl1 and Cl2 deviate by 0.075 (1) and -0.006 (1) Å, respectively, from the plane of the attached benzene ring (C11–C16). The sum of angles at N1 atom of the thiazepin ring (360.0°) is in accordance with sp² hybridization. The geometric parameters of the title molecule agree well with those reported for similar structures (Bakthadoss et al., 2013).

The molecular conformation is stabilized by a weak intramolecular C10—H10B···Cl1 hydrogen bond, which generates an S(5) ring motif (Bernstein et al., 1995). In the crystal packing, molecules are linked by N1—H1A···O1 hydrogen bonds into cyclic centrosymmetric R₂²(8) dimers (Fig. 2 and Table 1). The crystal packing is further stabilized by alternating π–π interactions with Cg1···Cg1ⁱⁱ = 3.740 (3) Å (symmetry code: (ii) = 2-x, -y, 2-z) and Cg2···Cg2ⁱⁱⁱ = 3.882 (3) Å (symmetry code: (iii) = 1-x, 1-y, 1-z) forming supramolecular stacks along the a axis (Fig. 3; Cg1 and Cg2 are the centroids of the C2–C7 and C11–C16 benzene rings, respectively).

Related literature top

For background to the biology and related structures of thiazepin derivatives, see: Bakthadoss et al. (2013). For ring-puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of (Z)-methyl 2-(bromomethyl)-3-(2,4-dichlorophenyl)acrylate 2 mmol) and o-aminothiophenol (2 mmol) in the presence of potassium tert-butoxide (4.8 mmol) in dry THF (10 ml) was stirred at room temperature for 1 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (20 ml) and extracted with ethyl acetate (3 x 20 ml). The organic layer was washed with brine (2 x 20 ml) and dried over anhydrous sodium sulfate. The organic layer was concentrated, which successfully provide the crude final product ((Z)-3-(2,4dichlorobenzyl)benzo[b][1,4]thiazepin-4(5H)-one). The final product was purified by column chromatography on silica gel to afford the title compound in good yield (42%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of its ethylacetate solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound showing displacement ellipsoids at the 30% probability level. H atoms are presented as a small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of the title compound showing N—H···O intermolecular hydrogen bonds (dotted lines) generating R²₂(8) centrosymmetric dimers [Symmetry code: (i) 2-x, 1-y, 2-z].
	Fig. 3. A view of alternating π—π interactions forming supramolecular stacks along the a axis in the crystal structure of the title compound. Cg1 and Cg2 are the centroids of the (C2–C7) and (C11–C16) benzene rings, respectively [Symmetry code: (ii) 2-x, -y, 2-z; (iii) 1-x, 1-y, 1-z; (iv) -1+x, 1+y, -1+z; (v) -x, 2-y, -z].

(Z)-3-(2,4-Dichlorobenzyl)-1,5-benzothiazepin-4(5H)-one top

Crystal data top

C₁₆H₁₁Cl₂NOS	Z = 2
M_r = 336.22	F(000) = 344
Triclinic, P1	D_x = 1.510 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.879 (5) Å	Cell parameters from 5914 reflections
b = 9.667 (5) Å	θ = 2.1–33.7°
c = 9.979 (5) Å	µ = 0.58 mm⁻¹
α = 89.052 (5)°	T = 293 K
β = 78.161 (4)°	Block, colourless
γ = 83.647 (5)°	0.24 × 0.21 × 0.15 mm
V = 739.3 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	5225 independent reflections
Radiation source: fine-focus sealed tube	4013 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.0 pixels mm^-1	θ_max = 33.7°, θ_min = 2.1°
ω scans	h = −12→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
T_min = 0.871, T_max = 0.917	l = −14→15
18415 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0583P)² + 0.2157P] where P = (F_o² + 2F_c²)/3
5225 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₆H₁₁Cl₂NOS	γ = 83.647 (5)°
M_r = 336.22	V = 739.3 (7) Å³
Triclinic, P1	Z = 2
a = 7.879 (5) Å	Mo Kα radiation
b = 9.667 (5) Å	µ = 0.58 mm⁻¹
c = 9.979 (5) Å	T = 293 K
α = 89.052 (5)°	0.24 × 0.21 × 0.15 mm
β = 78.161 (4)°

Data collection top

Bruker APEXII CCD diffractometer	5225 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4013 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.917	R_int = 0.026
18415 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.04	Δρ_max = 0.55 e Å⁻³
5225 reflections	Δρ_min = −0.44 e Å⁻³
190 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
C1	0.53450 (18)	0.28937 (15)	0.94205 (15)	0.0366 (3)
H1	0.4546	0.2673	0.8911	0.044*
C2	0.6952 (2)	0.14986 (15)	1.12880 (14)	0.0371 (3)
C3	0.6971 (3)	0.01550 (17)	1.18247 (17)	0.0510 (4)
H3	0.5951	−0.0277	1.1996	0.061*
C4	0.8473 (3)	−0.05324 (19)	1.21016 (19)	0.0622 (5)
H4	0.8466	−0.1424	1.2467	0.075*
C5	0.9993 (3)	0.0092 (2)	1.18406 (19)	0.0600 (5)
H5	1.1010	−0.0374	1.2038	0.072*
C6	1.0008 (2)	0.14161 (19)	1.12835 (17)	0.0469 (3)
H6	1.1037	0.1836	1.1106	0.056*
C7	0.84959 (19)	0.21138 (14)	1.09904 (14)	0.0352 (3)
C8	0.79730 (18)	0.41136 (14)	0.94238 (15)	0.0349 (3)
C9	0.66727 (17)	0.35381 (13)	0.87569 (14)	0.0321 (2)
C10	0.6884 (2)	0.39317 (17)	0.72620 (15)	0.0423 (3)
H10A	0.6968	0.4924	0.7186	0.051*
H10B	0.7978	0.3460	0.6767	0.051*
C11	0.5449 (2)	0.35964 (15)	0.65712 (14)	0.0371 (3)
C12	0.55727 (19)	0.24270 (15)	0.57559 (15)	0.0359 (3)
C13	0.42879 (19)	0.21821 (15)	0.50589 (15)	0.0388 (3)
H13	0.4419	0.1402	0.4499	0.047*
C14	0.28122 (19)	0.31163 (16)	0.52118 (14)	0.0390 (3)
C15	0.2600 (2)	0.42737 (18)	0.60401 (18)	0.0477 (4)
H15	0.1583	0.4886	0.6158	0.057*
C16	0.3933 (2)	0.45071 (17)	0.66928 (17)	0.0469 (4)
H16	0.3808	0.5302	0.7232	0.056*
N1	0.85975 (16)	0.34776 (12)	1.04633 (13)	0.0375 (3)
H1A	0.9155	0.3990	1.0879	0.045*
O1	0.84965 (17)	0.52292 (12)	0.89978 (14)	0.0545 (3)
Cl1	0.73749 (6)	0.11906 (5)	0.55837 (6)	0.06427 (15)
Cl2	0.11969 (6)	0.27905 (6)	0.43563 (5)	0.05837 (14)
S1	0.49323 (5)	0.24136 (4)	1.11466 (4)	0.04389 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0354 (7)	0.0435 (7)	0.0355 (7)	−0.0151 (5)	−0.0122 (5)	0.0003 (5)
C2	0.0443 (7)	0.0377 (6)	0.0304 (6)	−0.0118 (5)	−0.0059 (5)	0.0013 (5)
C3	0.0692 (11)	0.0425 (8)	0.0405 (8)	−0.0178 (8)	−0.0032 (7)	0.0067 (6)
C4	0.0933 (16)	0.0444 (9)	0.0444 (9)	−0.0023 (9)	−0.0077 (9)	0.0139 (7)
C5	0.0720 (13)	0.0603 (11)	0.0463 (9)	0.0113 (9)	−0.0196 (9)	0.0086 (8)
C6	0.0460 (8)	0.0559 (9)	0.0417 (8)	−0.0047 (7)	−0.0169 (7)	0.0046 (7)
C7	0.0413 (7)	0.0372 (6)	0.0298 (6)	−0.0090 (5)	−0.0111 (5)	0.0016 (5)
C8	0.0351 (6)	0.0342 (6)	0.0405 (7)	−0.0127 (5)	−0.0153 (5)	0.0023 (5)
C9	0.0344 (6)	0.0322 (6)	0.0339 (6)	−0.0106 (5)	−0.0129 (5)	−0.0001 (5)
C10	0.0475 (8)	0.0506 (8)	0.0355 (7)	−0.0246 (7)	−0.0142 (6)	0.0037 (6)
C11	0.0453 (7)	0.0411 (7)	0.0295 (6)	−0.0162 (6)	−0.0121 (5)	0.0028 (5)
C12	0.0359 (7)	0.0376 (6)	0.0369 (7)	−0.0105 (5)	−0.0103 (5)	0.0015 (5)
C13	0.0416 (7)	0.0419 (7)	0.0367 (7)	−0.0144 (6)	−0.0114 (6)	−0.0024 (5)
C14	0.0392 (7)	0.0492 (8)	0.0328 (6)	−0.0151 (6)	−0.0121 (5)	0.0086 (5)
C15	0.0457 (8)	0.0507 (9)	0.0466 (8)	0.0005 (7)	−0.0122 (7)	−0.0001 (7)
C16	0.0563 (10)	0.0449 (8)	0.0416 (8)	−0.0057 (7)	−0.0144 (7)	−0.0072 (6)
N1	0.0406 (6)	0.0388 (6)	0.0405 (6)	−0.0169 (5)	−0.0194 (5)	0.0046 (5)
O1	0.0638 (8)	0.0471 (6)	0.0703 (8)	−0.0323 (6)	−0.0422 (6)	0.0212 (5)
Cl1	0.0451 (2)	0.0557 (3)	0.0965 (4)	0.00095 (18)	−0.0269 (2)	−0.0159 (2)
Cl2	0.0465 (2)	0.0776 (3)	0.0608 (3)	−0.0192 (2)	−0.0275 (2)	0.0075 (2)
S1	0.03570 (19)	0.0574 (2)	0.0392 (2)	−0.01553 (16)	−0.00402 (14)	0.00582 (15)

Geometric parameters (Å, º) top

C1—C9	1.3294 (19)	C8—C9	1.4901 (18)
C1—S1	1.7508 (17)	C9—C10	1.514 (2)
C1—H1	0.9300	C10—C11	1.505 (2)
C2—C7	1.388 (2)	C10—H10A	0.9700
C2—C3	1.396 (2)	C10—H10B	0.9700
C2—S1	1.7642 (18)	C11—C12	1.387 (2)
C3—C4	1.368 (3)	C11—C16	1.389 (2)
C3—H3	0.9300	C12—C13	1.383 (2)
C4—C5	1.376 (3)	C12—Cl1	1.7336 (17)
C4—H4	0.9300	C13—C14	1.375 (2)
C5—C6	1.387 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.377 (2)
C6—C7	1.385 (2)	C14—Cl2	1.7295 (16)
C6—H6	0.9300	C15—C16	1.384 (2)
C7—N1	1.4158 (19)	C15—H15	0.9300
C8—O1	1.2350 (17)	C16—H16	0.9300
C8—N1	1.3481 (19)	N1—H1A	0.8600

C9—C1—S1	127.26 (11)	C11—C10—H10A	108.3
C9—C1—H1	116.4	C9—C10—H10A	108.3
S1—C1—H1	116.4	C11—C10—H10B	108.3
C7—C2—C3	119.11 (15)	C9—C10—H10B	108.3
C7—C2—S1	121.99 (12)	H10A—C10—H10B	107.4
C3—C2—S1	118.67 (13)	C12—C11—C16	116.63 (14)
C4—C3—C2	120.73 (17)	C12—C11—C10	123.35 (15)
C4—C3—H3	119.6	C16—C11—C10	119.97 (14)
C2—C3—H3	119.6	C13—C12—C11	122.51 (14)
C3—C4—C5	120.14 (17)	C13—C12—Cl1	117.07 (12)
C3—C4—H4	119.9	C11—C12—Cl1	120.42 (12)
C5—C4—H4	119.9	C14—C13—C12	118.59 (14)
C4—C5—C6	119.97 (18)	C14—C13—H13	120.7
C4—C5—H5	120.0	C12—C13—H13	120.7
C6—C5—H5	120.0	C13—C14—C15	121.28 (14)
C7—C6—C5	120.20 (17)	C13—C14—Cl2	118.34 (12)
C7—C6—H6	119.9	C15—C14—Cl2	120.38 (13)
C5—C6—H6	119.9	C14—C15—C16	118.61 (16)
C6—C7—C2	119.78 (14)	C14—C15—H15	120.7
C6—C7—N1	117.04 (13)	C16—C15—H15	120.7
C2—C7—N1	123.08 (13)	C15—C16—C11	122.33 (15)
O1—C8—N1	118.83 (12)	C15—C16—H16	118.8
O1—C8—C9	117.93 (12)	C11—C16—H16	118.8
N1—C8—C9	123.23 (12)	C8—N1—C7	131.25 (11)
C1—C9—C8	124.33 (13)	C8—N1—H1A	114.4
C1—C9—C10	122.86 (12)	C7—N1—H1A	114.4
C8—C9—C10	112.36 (11)	C1—S1—C2	101.45 (7)
C11—C10—C9	115.75 (12)

C7—C2—C3—C4	2.3 (2)	C16—C11—C12—C13	1.8 (2)
S1—C2—C3—C4	−172.38 (14)	C10—C11—C12—C13	−175.75 (13)
C2—C3—C4—C5	−0.6 (3)	C16—C11—C12—Cl1	−177.66 (12)
C3—C4—C5—C6	−0.6 (3)	C10—C11—C12—Cl1	4.7 (2)
C4—C5—C6—C7	0.1 (3)	C11—C12—C13—C14	−1.8 (2)
C5—C6—C7—C2	1.6 (2)	Cl1—C12—C13—C14	177.71 (11)
C5—C6—C7—N1	178.10 (15)	C12—C13—C14—C15	−0.1 (2)
C3—C2—C7—C6	−2.8 (2)	C12—C13—C14—Cl2	−179.09 (11)
S1—C2—C7—C6	171.71 (12)	C13—C14—C15—C16	1.9 (2)
C3—C2—C7—N1	−179.04 (14)	Cl2—C14—C15—C16	−179.17 (13)
S1—C2—C7—N1	−4.5 (2)	C14—C15—C16—C11	−1.8 (3)
S1—C1—C9—C8	−7.0 (2)	C12—C11—C16—C15	0.0 (2)
S1—C1—C9—C10	−178.71 (12)	C10—C11—C16—C15	177.70 (15)
O1—C8—C9—C1	−141.76 (16)	O1—C8—N1—C7	−167.01 (16)
N1—C8—C9—C1	38.2 (2)	C9—C8—N1—C7	13.1 (2)
O1—C8—C9—C10	30.69 (19)	C6—C7—N1—C8	135.73 (17)
N1—C8—C9—C10	−149.37 (15)	C2—C7—N1—C8	−47.9 (2)
C1—C9—C10—C11	2.2 (2)	C9—C1—S1—C2	−51.65 (16)
C8—C9—C10—C11	−170.34 (13)	C7—C2—S1—C1	58.57 (13)
C9—C10—C11—C12	−98.99 (18)	C3—C2—S1—C1	−126.89 (13)
C9—C10—C11—C16	83.49 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···Cl1	0.97	2.64	3.103 (3)	109
N1—H1A···O1ⁱ	0.86	2.10	2.873 (2)	149

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁Cl₂NOS
M_r	336.22
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.879 (5), 9.667 (5), 9.979 (5)
α, β, γ (°)	89.052 (5), 78.161 (4), 83.647 (5)
V (Å³)	739.3 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.24 × 0.21 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.871, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	18415, 5225, 4013
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.781

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.123, 1.04
No. of reflections	5225
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.44

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···Cl1	0.97	2.64	3.103 (3)	109
N1—H1A···O1ⁱ	0.86	2.10	2.873 (2)	149

Symmetry code: (i) −x+2, −y+1, −z+2.

Footnotes

‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for the data collection.

References

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