8,11,24-Trioxa-21-thia-19-aza­penta­cyclo­[16.6.0.02,7.012,17.019,23]tetra­cosa-2(7),3,5,12,14,16-hexa­ene

Devi, S.K.; Srinivasan, T.; Purushothaman, S.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536813012798

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o898

doi:10.1107/S1600536813012798

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8,11,24-Trioxa-21-thia-19-azapentacyclo[16.6.0.0^2,7.0^12,17.0^19,23]tetracosa-2(7),3,5,12,14,16-hexaene

Seenivasan Karthiga Devi,^a Thothadri Srinivasan,^a Santhanagopalan Purushothaman,^b Raghavachary Raghunathan ^b and Devadasan Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 27 April 2013; accepted 9 May 2013; online 15 May 2013)

In the title compound, C₁₉H₁₉NO₃S, the thiazole and oxazolidine rings each adopt an envelope conformation, with the S and O atoms as the respective flap atoms. The thiazole and oxazolidine rings (all atoms) make a dihedral angle of 66.39 (11)° while the phenyl rings subtend a dihedral angle of 22.71 (10)°.

Related literature

For the biological activity of thiazole derivatives, see: Guo et al. (2006 ); Karegoudar et al. (2008 ); Reddy et al. (1999 ).

Experimental

Crystal data

C₁₉H₁₉NO₃S
M_r = 341.42
Monoclinic, P 2₁ /c
a = 10.725 (5) Å
b = 10.405 (5) Å
c = 14.930 (5) Å
β = 100.262 (5)°
V = 1639.4 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.938, T_max = 0.958
15331 measured reflections
4067 independent reflections
2586 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.149
S = 1.03
4067 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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/S1600536813012798/bt6902sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012798/bt6902Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012798/bt6902Isup3.cml

checkCIF report

Comment top

Thiazole derivatives have a varity of physiological effects, such as antiinflammatory (Guo et al., 2006) and antimicrobial (Karegoudar et al., 2008). Against this background, we report herein the crystal structure of the title compound.

In the title compound, C₁₉H₁₉NO₃S, (Fig. 1) both the thiazole ring and the oxazolidine ring adopt an envelope conformation. The thiazole ring (S1/N1/C17/C18/C19) makes a dihedral angle of 66.39 (11)° with the oxazolidine ring (O3/N1/C7/C8/C17). The thiazole ring makes a dihedral angle of 61.25 (11)° with the phenyl ring (C1-C6), it makes a dihedral angle of 79.60 (11)° with the other phenyl ring (C9-C14).

The oxazolidine ring makes a dihedral angle of 64.80 (11)° with the phenyl ring (C1-C6), it makes a dihedral angle of 67.26 (10)° with the other phenyl ring (C9-C14). The dihedral angle between the two phenyl rings is 22.71 (10)°. The molecular structure features weak intramolecular C–H···O and C–H···N hydrogen bonds (Table 1).

Related literature top

For the biological activity of thiazole derivatives, see: Guo et al. (2006); Karegoudar et al. (2008); Reddy et al. (1999).

Experimental top

A mixture of 2,2'-(ethane-1,2-diylbis(oxy))dibenzaldehyde (1 mMol) and thiazolidine-4-carboxylic acid (1 mMol) was refluxed in acetonitrile (30ml) for about 5 hrs under N₂ atm. After the completion of reaction as indicated by TLC, acetonitrile was evaporated under reduced pressure. The crude product was purified by column chromatography using hexane: EtOAc (8:2) mixture as eluent. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

8,11,24-Trioxa-21-thia-19-azapentacyclo[16.6.0.0^2,7.0^12,17.0^19,23]tetracosa-2(7),3,5,12,14,16-hexaene top

Crystal data top

C₁₉H₁₉NO₃S	F(000) = 720
M_r = 341.42	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4067 reflections
a = 10.725 (5) Å	θ = 1.9–28.4°
b = 10.405 (5) Å	µ = 0.22 mm⁻¹
c = 14.930 (5) Å	T = 293 K
β = 100.262 (5)°	Block, colourless
V = 1639.4 (12) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	4067 independent reflections
Radiation source: fine-focus sealed tube	2586 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
T_min = 0.938, T_max = 0.958	k = −13→13
15331 measured reflections	l = −19→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0712P)² + 0.3653P] where P = (F_o² + 2F_c²)/3
4067 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₉H₁₉NO₃S	V = 1639.4 (12) Å³
M_r = 341.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.725 (5) Å	µ = 0.22 mm⁻¹
b = 10.405 (5) Å	T = 293 K
c = 14.930 (5) Å	0.30 × 0.25 × 0.20 mm
β = 100.262 (5)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	4067 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2586 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.958	R_int = 0.030
15331 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.03	Δρ_max = 0.64 e Å⁻³
4067 reflections	Δρ_min = −0.34 e Å⁻³
217 parameters

Special details top

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.

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 > 2sigma(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	0.67608 (18)	0.00360 (19)	0.35262 (13)	0.0435 (4)
C2	0.5857 (2)	0.0394 (2)	0.40363 (16)	0.0580 (6)
H2	0.5126	−0.0095	0.4013	0.070*
C3	0.6040 (3)	0.1464 (3)	0.45719 (16)	0.0685 (7)
H3	0.5437	0.1692	0.4920	0.082*
C4	0.7105 (3)	0.2208 (2)	0.46029 (16)	0.0661 (7)
H4	0.7221	0.2943	0.4963	0.079*
C5	0.8005 (2)	0.1848 (2)	0.40896 (14)	0.0556 (5)
H5	0.8725	0.2352	0.4109	0.067*
C6	0.78602 (17)	0.07568 (18)	0.35488 (12)	0.0417 (4)
C7	0.88455 (17)	0.03869 (17)	0.29832 (12)	0.0386 (4)
H7	0.8874	−0.0551	0.2933	0.046*
C8	0.85966 (16)	0.09868 (18)	0.20073 (12)	0.0404 (4)
H8	0.8024	0.1723	0.1992	0.048*
C9	0.80786 (17)	0.00603 (18)	0.12575 (12)	0.0401 (4)
C10	0.8866 (2)	−0.0566 (2)	0.07553 (13)	0.0487 (5)
H10	0.9731	−0.0392	0.0872	0.058*
C11	0.8391 (2)	−0.1444 (2)	0.00832 (14)	0.0587 (6)
H11	0.8933	−0.1864	−0.0243	0.070*
C12	0.7101 (2)	−0.1691 (2)	−0.00986 (14)	0.0582 (6)
H12	0.6774	−0.2282	−0.0547	0.070*
C13	0.6300 (2)	−0.1062 (2)	0.03824 (14)	0.0517 (5)
H13	0.5434	−0.1224	0.0255	0.062*
C14	0.67837 (17)	−0.01947 (18)	0.10528 (12)	0.0404 (4)
C15	0.50032 (19)	−0.0129 (2)	0.18360 (16)	0.0538 (5)
H15A	0.4389	−0.0404	0.1314	0.065*
H15B	0.4584	0.0468	0.2184	0.065*
C16	0.54456 (18)	−0.1283 (2)	0.24204 (15)	0.0535 (5)
H16A	0.4819	−0.1488	0.2793	0.064*
H16B	0.5516	−0.2015	0.2031	0.064*
C17	1.05652 (19)	0.1675 (2)	0.27269 (14)	0.0507 (5)
H17	1.0490	0.2583	0.2885	0.061*
C18	1.1925 (2)	0.1351 (3)	0.27092 (18)	0.0690 (7)
H18A	1.2486	0.1820	0.3178	0.083*
H18B	1.2140	0.1560	0.2122	0.083*
C19	1.1041 (2)	−0.0106 (2)	0.37495 (17)	0.0653 (6)
H19A	1.0625	−0.0903	0.3861	0.078*
H19B	1.1540	0.0186	0.4320	0.078*
N1	1.01005 (14)	0.08607 (16)	0.33910 (11)	0.0472 (4)
O1	0.66449 (12)	−0.10640 (12)	0.29984 (9)	0.0473 (3)
O2	0.60208 (12)	0.05173 (13)	0.15245 (9)	0.0488 (4)
O3	0.98101 (12)	0.14160 (14)	0.18684 (9)	0.0507 (4)
S1	1.20505 (6)	−0.03571 (7)	0.29167 (6)	0.0782 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0465 (10)	0.0417 (10)	0.0441 (10)	0.0101 (8)	0.0126 (8)	0.0106 (8)
C2	0.0566 (13)	0.0594 (14)	0.0645 (13)	0.0105 (10)	0.0288 (11)	0.0127 (11)
C3	0.0815 (18)	0.0714 (16)	0.0609 (14)	0.0299 (14)	0.0351 (13)	0.0091 (12)
C4	0.0878 (18)	0.0574 (14)	0.0537 (12)	0.0204 (13)	0.0147 (12)	−0.0083 (11)
C5	0.0636 (13)	0.0524 (13)	0.0502 (11)	0.0061 (10)	0.0086 (10)	−0.0087 (10)
C6	0.0450 (10)	0.0420 (10)	0.0374 (9)	0.0067 (8)	0.0053 (8)	0.0034 (8)
C7	0.0368 (9)	0.0384 (10)	0.0402 (9)	0.0004 (7)	0.0064 (7)	−0.0012 (8)
C8	0.0376 (9)	0.0396 (10)	0.0436 (9)	−0.0009 (7)	0.0061 (7)	0.0032 (8)
C9	0.0437 (10)	0.0402 (10)	0.0353 (8)	0.0010 (8)	0.0045 (8)	0.0072 (8)
C10	0.0463 (11)	0.0575 (13)	0.0429 (10)	0.0006 (9)	0.0090 (8)	0.0003 (9)
C11	0.0670 (14)	0.0629 (14)	0.0479 (11)	0.0057 (11)	0.0153 (10)	−0.0063 (10)
C12	0.0724 (15)	0.0548 (13)	0.0444 (11)	−0.0044 (11)	0.0025 (10)	−0.0077 (10)
C13	0.0488 (11)	0.0515 (12)	0.0514 (11)	−0.0051 (9)	−0.0007 (9)	0.0001 (10)
C14	0.0410 (10)	0.0410 (10)	0.0379 (9)	0.0019 (8)	0.0036 (8)	0.0063 (8)
C15	0.0374 (10)	0.0616 (13)	0.0622 (12)	0.0019 (9)	0.0083 (9)	0.0054 (11)
C16	0.0416 (11)	0.0523 (13)	0.0676 (13)	−0.0057 (9)	0.0127 (10)	0.0010 (10)
C17	0.0539 (12)	0.0419 (11)	0.0545 (11)	−0.0115 (9)	0.0044 (9)	−0.0019 (9)
C18	0.0471 (12)	0.0852 (18)	0.0733 (15)	−0.0232 (12)	0.0072 (11)	0.0086 (14)
C19	0.0432 (11)	0.0781 (16)	0.0700 (14)	0.0011 (11)	−0.0025 (10)	0.0228 (13)
N1	0.0386 (8)	0.0540 (10)	0.0465 (9)	−0.0036 (7)	0.0012 (7)	−0.0003 (8)
O1	0.0407 (7)	0.0416 (8)	0.0598 (8)	0.0031 (6)	0.0095 (6)	0.0025 (6)
O2	0.0420 (7)	0.0461 (8)	0.0591 (8)	0.0028 (6)	0.0114 (6)	0.0029 (6)
O3	0.0468 (8)	0.0582 (9)	0.0470 (7)	−0.0132 (6)	0.0076 (6)	0.0059 (7)
S1	0.0494 (4)	0.0816 (5)	0.1040 (6)	0.0119 (3)	0.0148 (3)	−0.0004 (4)

Geometric parameters (Å, º) top

C1—O1	1.383 (2)	C12—C13	1.378 (3)
C1—C2	1.386 (3)	C12—H12	0.9300
C1—C6	1.393 (3)	C13—C14	1.379 (3)
C2—C3	1.364 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—O2	1.386 (2)
C3—C4	1.374 (4)	C15—O2	1.428 (2)
C3—H3	0.9300	C15—C16	1.510 (3)
C4—C5	1.386 (3)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.386 (3)	C16—O1	1.434 (2)
C5—H5	0.9300	C16—H16A	0.9700
C6—C7	1.515 (3)	C16—H16B	0.9700
C7—N1	1.461 (2)	C17—O3	1.415 (2)
C7—C8	1.564 (2)	C17—N1	1.458 (3)
C7—H7	0.9800	C17—C18	1.501 (3)
C8—O3	1.426 (2)	C17—H17	0.9800
C8—C9	1.506 (3)	C18—S1	1.805 (3)
C8—H8	0.9800	C18—H18A	0.9700
C9—C10	1.388 (3)	C18—H18B	0.9700
C9—C14	1.393 (3)	C19—N1	1.457 (3)
C10—C11	1.386 (3)	C19—S1	1.808 (3)
C10—H10	0.9300	C19—H19A	0.9700
C11—C12	1.386 (3)	C19—H19B	0.9700
C11—H11	0.9300

O1—C1—C2	122.33 (19)	C12—C13—H13	120.0
O1—C1—C6	116.70 (16)	C14—C13—H13	120.0
C2—C1—C6	120.9 (2)	C13—C14—O2	122.64 (17)
C3—C2—C1	120.0 (2)	C13—C14—C9	121.01 (18)
C3—C2—H2	120.0	O2—C14—C9	116.27 (16)
C1—C2—H2	120.0	O2—C15—C16	112.49 (16)
C2—C3—C4	120.8 (2)	O2—C15—H15A	109.1
C2—C3—H3	119.6	C16—C15—H15A	109.1
C4—C3—H3	119.6	O2—C15—H15B	109.1
C3—C4—C5	119.0 (2)	C16—C15—H15B	109.1
C3—C4—H4	120.5	H15A—C15—H15B	107.8
C5—C4—H4	120.5	O1—C16—C15	112.16 (16)
C4—C5—C6	121.8 (2)	O1—C16—H16A	109.2
C4—C5—H5	119.1	C15—C16—H16A	109.2
C6—C5—H5	119.1	O1—C16—H16B	109.2
C5—C6—C1	117.49 (18)	C15—C16—H16B	109.2
C5—C6—C7	121.07 (18)	H16A—C16—H16B	107.9
C1—C6—C7	121.41 (17)	O3—C17—N1	107.18 (15)
N1—C7—C6	111.36 (15)	O3—C17—C18	110.00 (18)
N1—C7—C8	104.20 (14)	N1—C17—C18	109.38 (18)
C6—C7—C8	113.43 (14)	O3—C17—H17	110.1
N1—C7—H7	109.2	N1—C17—H17	110.1
C6—C7—H7	109.2	C18—C17—H17	110.1
C8—C7—H7	109.2	C17—C18—S1	105.17 (14)
O3—C8—C9	108.52 (14)	C17—C18—H18A	110.7
O3—C8—C7	104.59 (14)	S1—C18—H18A	110.7
C9—C8—C7	114.59 (15)	C17—C18—H18B	110.7
O3—C8—H8	109.7	S1—C18—H18B	110.7
C9—C8—H8	109.7	H18A—C18—H18B	108.8
C7—C8—H8	109.7	N1—C19—S1	107.90 (15)
C10—C9—C14	118.11 (18)	N1—C19—H19A	110.1
C10—C9—C8	121.49 (17)	S1—C19—H19A	110.1
C14—C9—C8	120.40 (16)	N1—C19—H19B	110.1
C11—C10—C9	121.33 (19)	S1—C19—H19B	110.1
C11—C10—H10	119.3	H19A—C19—H19B	108.4
C9—C10—H10	119.3	C17—N1—C19	110.68 (17)
C12—C11—C10	119.3 (2)	C17—N1—C7	108.30 (15)
C12—C11—H11	120.3	C19—N1—C7	116.49 (17)
C10—C11—H11	120.3	C1—O1—C16	117.03 (14)
C13—C12—C11	120.2 (2)	C14—O2—C15	117.95 (16)
C13—C12—H12	119.9	C17—O3—C8	108.54 (14)
C11—C12—H12	119.9	C18—S1—C19	86.56 (12)
C12—C13—C14	120.0 (2)

O1—C1—C2—C3	177.59 (19)	C10—C9—C14—C13	1.2 (3)
C6—C1—C2—C3	−0.2 (3)	C8—C9—C14—C13	−178.50 (17)
C1—C2—C3—C4	1.0 (3)	C10—C9—C14—O2	−175.54 (16)
C2—C3—C4—C5	−0.8 (4)	C8—C9—C14—O2	4.7 (2)
C3—C4—C5—C6	−0.2 (3)	O2—C15—C16—O1	37.5 (3)
C4—C5—C6—C1	1.0 (3)	O3—C17—C18—S1	−83.13 (18)
C4—C5—C6—C7	179.23 (18)	N1—C17—C18—S1	34.3 (2)
O1—C1—C6—C5	−178.67 (16)	O3—C17—N1—C19	112.63 (19)
C2—C1—C6—C5	−0.8 (3)	C18—C17—N1—C19	−6.6 (2)
O1—C1—C6—C7	3.1 (2)	O3—C17—N1—C7	−16.2 (2)
C2—C1—C6—C7	−179.04 (17)	C18—C17—N1—C7	−135.44 (18)
C5—C6—C7—N1	27.6 (2)	S1—C19—N1—C17	−24.3 (2)
C1—C6—C7—N1	−154.15 (16)	S1—C19—N1—C7	100.01 (18)
C5—C6—C7—C8	−89.5 (2)	C6—C7—N1—C17	−122.40 (17)
C1—C6—C7—C8	88.7 (2)	C8—C7—N1—C17	0.25 (19)
N1—C7—C8—O3	15.47 (18)	C6—C7—N1—C19	112.12 (19)
C6—C7—C8—O3	136.75 (16)	C8—C7—N1—C19	−125.24 (18)
N1—C7—C8—C9	134.16 (16)	C2—C1—O1—C16	47.3 (2)
C6—C7—C8—C9	−104.56 (18)	C6—C1—O1—C16	−134.80 (18)
O3—C8—C9—C10	20.6 (2)	C15—C16—O1—C1	51.5 (2)
C7—C8—C9—C10	−95.9 (2)	C13—C14—O2—C15	44.0 (2)
O3—C8—C9—C14	−159.70 (16)	C9—C14—O2—C15	−139.28 (17)
C7—C8—C9—C14	83.8 (2)	C16—C15—O2—C14	55.3 (2)
C14—C9—C10—C11	−1.5 (3)	N1—C17—O3—C8	27.1 (2)
C8—C9—C10—C11	178.18 (18)	C18—C17—O3—C8	145.91 (17)
C9—C10—C11—C12	0.8 (3)	C9—C8—O3—C17	−148.93 (15)
C10—C11—C12—C13	0.3 (3)	C7—C8—O3—C17	−26.20 (19)
C11—C12—C13—C14	−0.6 (3)	C17—C18—S1—C19	−40.58 (17)
C12—C13—C14—O2	176.39 (17)	N1—C19—S1—C18	37.84 (17)
C12—C13—C14—C9	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1	0.93	2.51	2.834 (3)	101
C7—H7···O1	0.98	2.47	2.805 (3)	100
C10—H10···O3	0.93	2.39	2.728 (3)	101

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉NO₃S
M_r	341.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.725 (5), 10.405 (5), 14.930 (5)
β (°)	100.262 (5)
V (Å³)	1639.4 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.938, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	15331, 4067, 2586
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.149, 1.03
No. of reflections	4067
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.34

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

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SK,TS and DV acknowlege the UGC (SAP–CAS) for the departmental facilties. SK thanks the DST PURSE for a Junior Research Fellowship and TS thanks the DST Inspire for a fellowship.

References

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