3-(4-Methoxybenzyl)-1,5-benzo­thiazepin-4(5H)-one

Selvakumar, R.; Bakthadoss, M.; Vijayakumar, S.; Murugavel, S.

doi:10.1107/S1600536813009215

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o693

https://doi.org/10.1107/S1600536813009215

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3-(4-Methoxybenzyl)-1,5-benzothiazepin-4(5H)-one

R. Selvakumar,^a M. Bakthadoss,^a,^b ‡ S. Vijayakumar ^c and S. Murugavel ^d ^*

^aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India, ^bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India, ^cDepartment of Physics, Sri Balaji Chokkalingam Engineering College, Arni, Thiruvannamalai 632 317, India, and ^dDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 31 March 2013; accepted 4 April 2013; online 10 April 2013)

In the title compound, C₁₇H₁₅NO₂S, the thiazepine ring adopts a slightly distorted twist-boat conformation. The dihedral angle between the mean plane of the benzothiazepin ring system and the benzene ring is 65.7 (1)°. In the crystal, pairs of N—H⋯O hydrogen bonds link inversion-related molecules into dimers, generating R₂²(8) ring motifs. These dimers are further linked by C—H⋯π and π–π interactions [inter-centroid distance between the benzene rings of the benzothiazepine unit = 3.656 (3) Å] into a three-dimensional supramolecular network.

Related literature

For background to the biology of thiazepin derivatives and for a related structure, see: Bakthadoss et al. (2013 ). For ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₁₅NO₂S
M_r = 297.36
Triclinic, $[P \overline 1]$
a = 7.678 (5) Å
b = 9.612 (5) Å
c = 10.860 (5) Å
α = 77.208 (5)°
β = 74.117 (4)°
γ = 81.522 (5)°
V = 748.5 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.951, T_max = 0.968
18449 measured reflections
5363 independent reflections
3676 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.134
S = 1.05
5363 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.02	2.860 (2)	167
C17—H17B⋯Cgⁱⁱ	0.96	2.96	3.561 (3)	122
Symmetry codes: (i) -x, -y+1, -z; (ii) x+1, y+1, z.

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: https://doi.org/10.1107/S1600536813009215/sj5315sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009215/sj5315Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009215/sj5315Isup3.cml

checkCIF report

Comment top

The background to the biology of thiazepin derivatives and a related structure have 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 slightly distorted twist-boat conformation as indicated by puckering parameters (Cremer & Pople, 1975) QT = 0.9884 (11) Å, φ₂ = 357.9 (1)° and φ₃ = 355.6 (3)°. The dihedral angle between the benzothiazepin ring system and the benzene ring is 65.7 (1) (1)°. The atom O1 deviates by -0.458 (1) Å from the least-squares plane of the thiazepin ring. The sum of angles at N1 atom of the thiazepin ring (359.9⁰) is in accordance with sp² hybridization. The geometric parameters of the title molecule agree well with those reported for a similar structure (Bakthadoss et al., 2013).

In the crystal, molecules are linked by N1—H1A···O1 hydrogen bonds into cylic centrosymmetric R₂²(8) dimers (Fig. 2 and Table 1). These dimers are further linked by C17—H17B···Cgⁱⁱ (Table 1; Symmetry code:(ii) = 1 + x, 1 + y, z) hydrogen bonds and π—π interactions between benzothiazepine benzene rings with Cg···Cgⁱⁱⁱ = 3.656 (3) Å (Symmetry code:(iii) = -x, 1 - y, 1 - z) forming a three-dimensional supramolecular network (Fig. 3; Cg is the centroid of the C2–C7 benzene ring).

Related literature top

For background to the biology of thiazepin derivatives and for a related structure, see: Bakthadoss et al. (2013). For ring-puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of (Z)-methyl 2-(bromomethyl)-3-(4-methoxyphenyl)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. It was then concentrated to successfully provide the crude final product ((Z)-3-(4-methoxybenzyl)benzo[b][1,4]thiazepin-4(5H)-one). This was purified by column chromatography on silica gel with ethylacetate/hexane 1:19 as eluent to afford the title compound in good yield (45%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethylacetate solution at room temperature.

Structure description top

For background to the biology of thiazepin derivatives and for a related structure, see: Bakthadoss et al. (2013). For ring-puckering parameters, see: Cremer & Pople (1975).

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 an R²₂(8) centrosymmetric dimer. [Symmetry code: (i) -x, 1 - y, -z]. Hydrogen atoms not included in hydrogen bonding are omitted for clarity.
	Fig. 3. View of three-dimensional supramolecular network. The N—H···O, C—H···π and π—π interactions are shown as blue, red and green dashed lines, respectively. Cg is the centroid of the (C2···C7) benzene ring.[Symmetry code: (i) -x, 1 - y, -z; (ii) 1 + x, 1 + y, z; (iii) -x, 1 - y, 1 - z]. Hydrogen atoms not included in hydrogen bonding are omitted for clarity.

3-(4-Methoxybenzyl)-1,5-benzothiazepin-4(5H)-one top

Crystal data top

C₁₇H₁₅NO₂S	Z = 2
M_r = 297.36	F(000) = 312
Triclinic, P1	D_x = 1.319 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.678 (5) Å	Cell parameters from 5471 reflections
b = 9.612 (5) Å	θ = 2.0–32.6°
c = 10.860 (5) Å	µ = 0.22 mm⁻¹
α = 77.208 (5)°	T = 293 K
β = 74.117 (4)°	Block, colourless
γ = 81.522 (5)°	0.23 × 0.21 × 0.15 mm
V = 748.5 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	5363 independent reflections
Radiation source: fine-focus sealed tube	3676 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 32.6°, θ_min = 2.0°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
T_min = 0.951, T_max = 0.968	l = −15→16
18449 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0608P)² + 0.1157P] where P = (F_o² + 2F_c²)/3
5363 reflections	(Δ/σ)_max = 0.002
191 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₇H₁₅NO₂S	γ = 81.522 (5)°
M_r = 297.36	V = 748.5 (7) Å³
Triclinic, P1	Z = 2
a = 7.678 (5) Å	Mo Kα radiation
b = 9.612 (5) Å	µ = 0.22 mm⁻¹
c = 10.860 (5) Å	T = 293 K
α = 77.208 (5)°	0.23 × 0.21 × 0.15 mm
β = 74.117 (4)°

Data collection top

Bruker APEXII CCD diffractometer	5363 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3676 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.968	R_int = 0.027
18449 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	Δρ_max = 0.28 e Å⁻³
5363 reflections	Δρ_min = −0.33 e Å⁻³
191 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	0.42839 (17)	0.53284 (13)	0.19547 (13)	0.0389 (3)
H1	0.5174	0.5738	0.2152	0.047*
C2	0.18042 (19)	0.35576 (13)	0.34697 (13)	0.0404 (3)
C3	0.1350 (2)	0.29642 (16)	0.47950 (15)	0.0552 (4)
H3	0.2268	0.2590	0.5217	0.066*
C4	−0.0434 (3)	0.29249 (19)	0.54865 (16)	0.0639 (5)
H4	−0.0720	0.2511	0.6368	0.077*
C5	−0.1794 (2)	0.34965 (18)	0.48779 (16)	0.0595 (4)
H5	−0.3004	0.3466	0.5347	0.071*
C6	−0.1378 (2)	0.41157 (16)	0.35764 (14)	0.0475 (3)
H6	−0.2307	0.4514	0.3172	0.057*
C7	0.04227 (17)	0.41513 (13)	0.28606 (12)	0.0366 (3)
C8	0.19209 (16)	0.56421 (13)	0.07296 (12)	0.0344 (2)
C9	0.32623 (15)	0.61867 (13)	0.12345 (11)	0.0336 (2)
C10	0.34837 (18)	0.77722 (14)	0.07485 (14)	0.0415 (3)
H10A	0.3754	0.7968	−0.0196	0.050*
H10B	0.2336	0.8310	0.1066	0.050*
C11	0.49498 (17)	0.83050 (13)	0.11561 (13)	0.0377 (3)
C12	0.45462 (19)	0.90507 (15)	0.21596 (14)	0.0452 (3)
H12	0.3338	0.9228	0.2601	0.054*
C13	0.5907 (2)	0.95475 (16)	0.25307 (15)	0.0504 (3)
H13	0.5607	1.0052	0.3210	0.060*
C14	0.76966 (19)	0.92861 (14)	0.18852 (15)	0.0456 (3)
C15	0.81273 (19)	0.85446 (15)	0.08668 (16)	0.0497 (3)
H15	0.9335	0.8372	0.0423	0.060*
C16	0.67642 (19)	0.80638 (15)	0.05125 (15)	0.0462 (3)
H16	0.7066	0.7567	−0.0172	0.055*
C17	0.8784 (3)	1.0769 (2)	0.2951 (3)	0.0859 (7)
H17A	0.8026	1.1564	0.2609	0.129*
H17B	0.9907	1.1094	0.2953	0.129*
H17C	0.8171	1.0362	0.3825	0.129*
N1	0.07583 (14)	0.47009 (12)	0.15072 (10)	0.0391 (2)
H1A	0.0114	0.4382	0.1114	0.047*
O1	0.18656 (13)	0.60841 (11)	−0.04169 (9)	0.0456 (2)
O2	0.91500 (16)	0.97189 (13)	0.21607 (13)	0.0668 (3)
S1	0.41037 (5)	0.34901 (4)	0.25677 (4)	0.05008 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0361 (6)	0.0382 (6)	0.0460 (7)	−0.0061 (5)	−0.0172 (5)	−0.0053 (5)
C2	0.0500 (7)	0.0328 (6)	0.0419 (7)	−0.0089 (5)	−0.0177 (6)	−0.0033 (5)
C3	0.0772 (11)	0.0465 (8)	0.0470 (8)	−0.0166 (7)	−0.0288 (8)	0.0044 (6)
C4	0.0900 (13)	0.0610 (9)	0.0383 (8)	−0.0249 (9)	−0.0106 (8)	0.0002 (7)
C5	0.0627 (10)	0.0624 (9)	0.0476 (9)	−0.0190 (8)	0.0023 (7)	−0.0097 (7)
C6	0.0440 (7)	0.0525 (8)	0.0460 (8)	−0.0094 (6)	−0.0091 (6)	−0.0090 (6)
C7	0.0424 (6)	0.0363 (6)	0.0346 (6)	−0.0104 (5)	−0.0117 (5)	−0.0070 (5)
C8	0.0328 (6)	0.0381 (6)	0.0352 (6)	−0.0030 (4)	−0.0122 (5)	−0.0083 (5)
C9	0.0315 (5)	0.0364 (5)	0.0351 (6)	−0.0053 (4)	−0.0111 (5)	−0.0064 (4)
C10	0.0415 (7)	0.0381 (6)	0.0480 (7)	−0.0074 (5)	−0.0196 (6)	−0.0017 (5)
C11	0.0377 (6)	0.0320 (5)	0.0441 (7)	−0.0069 (5)	−0.0140 (5)	−0.0018 (5)
C12	0.0401 (7)	0.0446 (7)	0.0500 (8)	−0.0056 (5)	−0.0076 (6)	−0.0108 (6)
C13	0.0590 (9)	0.0453 (7)	0.0532 (8)	−0.0077 (6)	−0.0170 (7)	−0.0168 (6)
C14	0.0458 (7)	0.0337 (6)	0.0629 (9)	−0.0073 (5)	−0.0253 (6)	−0.0037 (6)
C15	0.0358 (7)	0.0471 (7)	0.0667 (10)	−0.0037 (5)	−0.0121 (6)	−0.0132 (7)
C16	0.0424 (7)	0.0462 (7)	0.0535 (8)	−0.0048 (5)	−0.0114 (6)	−0.0169 (6)
C17	0.0936 (15)	0.0580 (10)	0.138 (2)	−0.0058 (10)	−0.0690 (14)	−0.0361 (12)
N1	0.0399 (5)	0.0479 (6)	0.0349 (5)	−0.0135 (5)	−0.0146 (4)	−0.0064 (4)
O1	0.0453 (5)	0.0596 (6)	0.0358 (5)	−0.0154 (4)	−0.0168 (4)	−0.0019 (4)
O2	0.0591 (7)	0.0568 (6)	0.1027 (10)	−0.0091 (5)	−0.0422 (7)	−0.0231 (6)
S1	0.0448 (2)	0.03683 (18)	0.0684 (3)	0.00032 (13)	−0.02330 (17)	−0.00078 (15)

Geometric parameters (Å, º) top

C1—C9	1.3292 (18)	C10—C11	1.5061 (18)
C1—S1	1.7565 (15)	C10—H10A	0.9700
C1—H1	0.9300	C10—H10B	0.9700
C2—C7	1.3881 (19)	C11—C12	1.3758 (19)
C2—C3	1.392 (2)	C11—C16	1.388 (2)
C2—S1	1.7688 (17)	C12—C13	1.395 (2)
C3—C4	1.372 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.375 (2)
C4—C5	1.370 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—O2	1.3721 (17)
C5—C6	1.375 (2)	C14—C15	1.386 (2)
C5—H5	0.9300	C15—C16	1.378 (2)
C6—C7	1.389 (2)	C15—H15	0.9300
C6—H6	0.9300	C16—H16	0.9300
C7—N1	1.4124 (17)	C17—O2	1.415 (2)
C8—O1	1.2337 (16)	C17—H17A	0.9600
C8—N1	1.3474 (16)	C17—H17B	0.9600
C8—C9	1.4935 (16)	C17—H17C	0.9600
C9—C10	1.5170 (18)	N1—H1A	0.8600

C9—C1—S1	125.87 (10)	C9—C10—H10B	108.6
C9—C1—H1	117.1	H10A—C10—H10B	107.6
S1—C1—H1	117.1	C12—C11—C16	117.91 (12)
C7—C2—C3	119.01 (14)	C12—C11—C10	121.68 (12)
C7—C2—S1	120.68 (11)	C16—C11—C10	120.41 (12)
C3—C2—S1	120.27 (12)	C11—C12—C13	121.51 (13)
C4—C3—C2	120.83 (15)	C11—C12—H12	119.2
C4—C3—H3	119.6	C13—C12—H12	119.2
C2—C3—H3	119.6	C14—C13—C12	119.54 (13)
C5—C4—C3	119.96 (15)	C14—C13—H13	120.2
C5—C4—H4	120.0	C12—C13—H13	120.2
C3—C4—H4	120.0	O2—C14—C13	124.88 (14)
C4—C5—C6	120.22 (16)	O2—C14—C15	115.39 (13)
C4—C5—H5	119.9	C13—C14—C15	119.73 (12)
C6—C5—H5	119.9	C16—C15—C14	119.91 (13)
C5—C6—C7	120.46 (15)	C16—C15—H15	120.0
C5—C6—H6	119.8	C14—C15—H15	120.0
C7—C6—H6	119.8	C15—C16—C11	121.40 (13)
C2—C7—C6	119.49 (13)	C15—C16—H16	119.3
C2—C7—N1	122.61 (12)	C11—C16—H16	119.3
C6—C7—N1	117.72 (12)	O2—C17—H17A	109.5
O1—C8—N1	119.75 (10)	O2—C17—H17B	109.5
O1—C8—C9	118.99 (11)	H17A—C17—H17B	109.5
N1—C8—C9	121.26 (11)	O2—C17—H17C	109.5
C1—C9—C8	122.57 (11)	H17A—C17—H17C	109.5
C1—C9—C10	122.99 (11)	H17B—C17—H17C	109.5
C8—C9—C10	114.20 (10)	C8—N1—C7	130.70 (10)
C11—C10—C9	114.61 (10)	C8—N1—H1A	114.6
C11—C10—H10A	108.6	C7—N1—H1A	114.6
C9—C10—H10A	108.6	C14—O2—C17	117.51 (14)
C11—C10—H10B	108.6	C1—S1—C2	99.41 (6)

C7—C2—C3—C4	1.9 (2)	C9—C10—C11—C16	78.58 (16)
S1—C2—C3—C4	−175.66 (12)	C16—C11—C12—C13	−0.3 (2)
C2—C3—C4—C5	−1.1 (2)	C10—C11—C12—C13	−179.73 (13)
C3—C4—C5—C6	−0.3 (3)	C11—C12—C13—C14	−0.2 (2)
C4—C5—C6—C7	0.9 (2)	C12—C13—C14—O2	180.00 (14)
C3—C2—C7—C6	−1.28 (18)	C12—C13—C14—C15	0.6 (2)
S1—C2—C7—C6	176.27 (10)	O2—C14—C15—C16	−179.96 (13)
C3—C2—C7—N1	−176.30 (11)	C13—C14—C15—C16	−0.5 (2)
S1—C2—C7—N1	1.25 (16)	C14—C15—C16—C11	0.0 (2)
C5—C6—C7—C2	−0.1 (2)	C12—C11—C16—C15	0.4 (2)
C5—C6—C7—N1	175.17 (12)	C10—C11—C16—C15	179.84 (13)
S1—C1—C9—C8	−6.64 (19)	O1—C8—N1—C7	−172.86 (12)
S1—C1—C9—C10	179.39 (10)	C9—C8—N1—C7	6.0 (2)
O1—C8—C9—C1	−134.74 (14)	C2—C7—N1—C8	−51.01 (19)
N1—C8—C9—C1	46.39 (18)	C6—C7—N1—C8	133.88 (14)
O1—C8—C9—C10	39.71 (16)	C13—C14—O2—C17	−14.9 (2)
N1—C8—C9—C10	−139.16 (12)	C15—C14—O2—C17	164.55 (16)
C1—C9—C10—C11	−0.45 (19)	C9—C1—S1—C2	−57.47 (14)
C8—C9—C10—C11	−174.88 (11)	C7—C2—S1—C1	58.98 (11)
C9—C10—C11—C12	−102.00 (15)	C3—C2—S1—C1	−123.50 (11)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C3–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.02	2.860 (2)	167
C17—H17B···Cgⁱⁱ	0.96	2.96	3.561 (3)	122

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅NO₂S
M_r	297.36
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.678 (5), 9.612 (5), 10.860 (5)
α, β, γ (°)	77.208 (5), 74.117 (4), 81.522 (5)
V (Å³)	748.5 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.23 × 0.21 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.951, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	18449, 5363, 3676
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.134, 1.05
No. of reflections	5363
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.33

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

Cg is the centroid of the C3–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.02	2.860 (2)	166.8
C17—H17B···Cgⁱⁱ	0.96	2.96	3.561 (3)	122.0

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

Footnotes

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

Acknowledgements

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

References

Bakthadoss, M., Selvakumar, R., Manikandan, N. & Murugavel, S. (2013). Acta Cryst. E69, o562–o563. CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, U. S. A. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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