1-Ethyl-4-{2-[1-(4-methyl­phen­yl)ethyl­idene]hydrazinyl­idene}-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Tahir, M.N.; Harrison, W.T.A.; Bokhari, T.H.; Safder, M.

doi:10.1107/S1600536813000202

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o200

doi:10.1107/S1600536813000202

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1-Ethyl-4-{2-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq,^a ^* M. Nawaz Tahir,^b William T. A. Harrison,^c Tanveer Hussain Bokhari ^a and Muhammad Safder ^a

^aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, University of Aberdeen, Mston Walk, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: hafizshafique@hotmail.com

(Received 27 December 2012; accepted 3 January 2013; online 9 January 2013)

In the title compound, C₁₉H₂₁N₃O₂S, the dihedral angle between the aromatic rings is 6.7 (2)° and the C=N—N=C torsion angle is 178.0 (2)°. The conformation of the thiazine ring is an envelope, with the S atom displaced by 0.802 (2) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.022 Å). In the crystal, molecules are linked by C—H⋯O interactions, generating C(5) chains propagating in [010]. A weak C—H⋯π interaction is also observed.

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq et al. (2011a ). For further synthetic details, see: Shafiq et al. (2011b ). For a related structure, see: Shafiq et al. (2013 ).

Experimental

Crystal data

C₁₉H₂₁N₃O₂S
M_r = 355.45
Monoclinic, P 2₁ /n
a = 15.9018 (10) Å
b = 7.3716 (4) Å
c = 16.8376 (10) Å
β = 111.644 (3)°
V = 1834.57 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.34 × 0.26 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.937, T_max = 0.955
14168 measured reflections
3597 independent reflections
2598 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.139
S = 1.02
3597 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O2ⁱ	0.97	2.50	3.402 (4)	155
C9—H9A⋯Cg3ⁱⁱ	0.97	2.67	3.613 (2)	165
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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 (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813000202/ld2091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000202/ld2091Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000202/ld2091Isup3.cml

checkCIF report

Comment top

As a part of our ongoing studies of benzothiazine derivatives with potential biactivity (Shafiq et al., 2011a,b), we now describe the synthesis and structure of the title compound, (I).

The dihedral angle between the C1–C6 and C13–C18 aromatic rings is 6.68 (15)° and the C10=N2—N3=C11 torsion angle is 177.98 (19)°. The conformation of the C1/C6/C9/C10/N1/S1 thiazine ring is an envelope, with the S atom displaced by 0.802 (2) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.022 Å). A very similar conformation was observed in a related structure (Shafiq et al., 2013). Atoms C7 and C8 in (I) are displaced from the mean plane of the thiazine ring by -0.416 (5) and 0.704 (6) Å, respectively.

In the crystal, the moelcules are linked by C—H···O interactions (Table 1) to generate C(5) chains propagating in the b axis direction. A weak C—H···π interaction to the C13—C18 ring also occurs (Table 1).

Related literature top

For the synthesis and biological activity of the title compound and related materials, see: Shafiq et al. (2011a). For further synthetic details, see: Shafiq et al. (2011b). For a related structure, see: Shafiq et al. (2013).

Experimental top

4-Hydrazinylidene-1-ethyl-3H-2?6,1-benzothiazine-2,2-dione (Shafiq et al., 2011b) was reacted with para-methyl acetophenone according to literature procedure (Shafiq, et al., 2011a). The product obtained was re-crystallized from ethyl acetate solution to yield yellow prisms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 50% probability level.

1-Ethyl-4-{2-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3,4-dihydro- 1H-2λ⁶,1-benzothiazine-2,2-dione top

Crystal data top

C₁₉H₂₁N₃O₂S	F(000) = 752
M_r = 355.45	D_x = 1.287 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 335 reflections
a = 15.9018 (10) Å	θ = 3.1–23.5°
b = 7.3716 (4) Å	µ = 0.19 mm⁻¹
c = 16.8376 (10) Å	T = 296 K
β = 111.644 (3)°	Prism, yellow
V = 1834.57 (19) Å³	0.34 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3597 independent reflections
Radiation source: fine-focus sealed tube	2598 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −19→18
T_min = 0.937, T_max = 0.955	k = −9→8
14168 measured reflections	l = −18→20

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) = 0.139	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0649P)² + 0.6783P] where P = (F_o² + 2F_c²)/3
3597 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₉H₂₁N₃O₂S	V = 1834.57 (19) Å³
M_r = 355.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.9018 (10) Å	µ = 0.19 mm⁻¹
b = 7.3716 (4) Å	T = 296 K
c = 16.8376 (10) Å	0.34 × 0.26 × 0.24 mm
β = 111.644 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3597 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2598 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.955	R_int = 0.025
14168 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.02	Δρ_max = 0.45 e Å⁻³
3597 reflections	Δρ_min = −0.40 e Å⁻³
229 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	0.53653 (13)	0.1072 (3)	0.23121 (12)	0.0401 (5)
C2	0.62165 (14)	0.1299 (3)	0.22572 (14)	0.0504 (6)
H2	0.6306	0.2260	0.1940	0.060*
C3	0.69200 (16)	0.0146 (4)	0.26570 (16)	0.0610 (7)
H3	0.7478	0.0324	0.2609	0.073*
C4	0.67962 (16)	−0.1279 (4)	0.31306 (17)	0.0629 (7)
H4	0.7274	−0.2057	0.3411	0.076*
C5	0.59694 (17)	−0.1552 (3)	0.31882 (16)	0.0609 (7)
H5	0.5891	−0.2528	0.3504	0.073*
C6	0.52430 (14)	−0.0399 (3)	0.27836 (14)	0.0460 (5)
C7	0.4152 (2)	−0.2572 (4)	0.3072 (2)	0.0795 (9)
H7A	0.3511	−0.2787	0.2768	0.095*
H7B	0.4483	−0.3488	0.2894	0.095*
C8	0.4360 (3)	−0.2746 (6)	0.3986 (3)	0.1315 (16)
H8A	0.4972	−0.2366	0.4293	0.197*
H8B	0.4290	−0.3989	0.4121	0.197*
H8C	0.3954	−0.1999	0.4147	0.197*
C9	0.37033 (14)	0.2050 (3)	0.18892 (14)	0.0478 (5)
H9A	0.3372	0.1275	0.1410	0.057*
H9B	0.3380	0.3191	0.1820	0.057*
C10	0.46398 (13)	0.2394 (3)	0.18915 (12)	0.0411 (5)
C11	0.43384 (14)	0.6397 (3)	0.08403 (13)	0.0451 (5)
C12	0.52607 (16)	0.6781 (3)	0.08357 (17)	0.0603 (6)
H12A	0.5486	0.7891	0.1138	0.090*
H12B	0.5226	0.6896	0.0257	0.090*
H12C	0.5661	0.5804	0.1110	0.090*
C13	0.36016 (14)	0.7729 (3)	0.04561 (13)	0.0443 (5)
C14	0.36872 (17)	0.9137 (3)	−0.00555 (15)	0.0558 (6)
H14	0.4221	0.9255	−0.0157	0.067*
C15	0.30017 (17)	1.0357 (4)	−0.04138 (15)	0.0620 (7)
H15	0.3081	1.1287	−0.0753	0.074*
C16	0.21992 (17)	1.0238 (3)	−0.02836 (14)	0.0553 (6)
C17	0.21100 (16)	0.8847 (3)	0.02377 (14)	0.0532 (6)
H17	0.1578	0.8748	0.0344	0.064*
C18	0.27955 (15)	0.7613 (3)	0.05990 (13)	0.0497 (5)
H18	0.2719	0.6691	0.0943	0.060*
C19	0.1445 (2)	1.1567 (5)	−0.0695 (2)	0.0903 (10)
H19A	0.1632	1.2757	−0.0467	0.135*
H19B	0.0920	1.1212	−0.0580	0.135*
H19C	0.1301	1.1580	−0.1302	0.135*
S1	0.37561 (4)	0.10183 (9)	0.28376 (4)	0.0544 (2)
O1	0.42132 (12)	0.2209 (3)	0.35183 (11)	0.0773 (6)
O2	0.28939 (11)	0.0333 (3)	0.27645 (13)	0.0771 (6)
N1	0.43901 (13)	−0.0742 (3)	0.28385 (14)	0.0600 (6)
N2	0.48467 (12)	0.3786 (3)	0.15443 (12)	0.0536 (5)
N3	0.41244 (13)	0.4972 (3)	0.11660 (12)	0.0546 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0382 (11)	0.0417 (12)	0.0417 (10)	0.0006 (9)	0.0160 (8)	−0.0016 (9)
C2	0.0434 (12)	0.0530 (14)	0.0597 (13)	0.0020 (10)	0.0248 (10)	0.0066 (11)
C3	0.0432 (13)	0.0687 (17)	0.0777 (16)	0.0086 (11)	0.0300 (12)	0.0084 (14)
C4	0.0482 (14)	0.0678 (17)	0.0753 (16)	0.0203 (12)	0.0257 (12)	0.0186 (13)
C5	0.0576 (15)	0.0597 (16)	0.0716 (15)	0.0152 (12)	0.0311 (12)	0.0236 (13)
C6	0.0406 (12)	0.0484 (13)	0.0526 (12)	0.0046 (9)	0.0214 (9)	0.0069 (10)
C7	0.0672 (18)	0.071 (2)	0.109 (2)	−0.0089 (14)	0.0431 (17)	0.0118 (17)
C8	0.167 (4)	0.132 (4)	0.138 (3)	0.049 (3)	0.105 (3)	0.063 (3)
C9	0.0376 (11)	0.0468 (13)	0.0555 (12)	0.0009 (9)	0.0132 (9)	0.0071 (10)
C10	0.0383 (11)	0.0425 (12)	0.0425 (10)	0.0002 (9)	0.0146 (9)	0.0005 (9)
C11	0.0472 (12)	0.0440 (13)	0.0459 (11)	−0.0017 (9)	0.0194 (9)	0.0027 (10)
C12	0.0517 (14)	0.0525 (15)	0.0792 (16)	−0.0029 (11)	0.0272 (12)	0.0070 (13)
C13	0.0477 (12)	0.0415 (12)	0.0425 (10)	−0.0024 (9)	0.0150 (9)	0.0020 (9)
C14	0.0538 (14)	0.0563 (15)	0.0589 (13)	−0.0025 (11)	0.0227 (11)	0.0149 (11)
C15	0.0665 (16)	0.0588 (16)	0.0601 (14)	0.0018 (12)	0.0226 (12)	0.0227 (12)
C16	0.0605 (15)	0.0522 (14)	0.0467 (12)	0.0083 (11)	0.0122 (11)	0.0093 (11)
C17	0.0489 (13)	0.0597 (15)	0.0511 (12)	0.0041 (11)	0.0186 (10)	0.0026 (11)
C18	0.0528 (13)	0.0472 (13)	0.0492 (12)	−0.0005 (10)	0.0191 (10)	0.0074 (10)
C19	0.083 (2)	0.099 (2)	0.089 (2)	0.0348 (18)	0.0322 (17)	0.0373 (19)
S1	0.0401 (3)	0.0653 (4)	0.0638 (4)	0.0066 (3)	0.0262 (3)	0.0137 (3)
O1	0.0671 (12)	0.1064 (16)	0.0636 (10)	0.0069 (10)	0.0302 (9)	−0.0119 (10)
O2	0.0449 (10)	0.0878 (13)	0.1101 (15)	0.0094 (9)	0.0422 (10)	0.0334 (11)
N1	0.0461 (11)	0.0570 (13)	0.0836 (14)	0.0062 (9)	0.0316 (10)	0.0266 (11)
N2	0.0456 (11)	0.0509 (12)	0.0679 (12)	0.0070 (8)	0.0251 (9)	0.0179 (10)
N3	0.0481 (11)	0.0499 (12)	0.0687 (12)	0.0076 (9)	0.0249 (9)	0.0193 (10)

Geometric parameters (Å, º) top

C1—C6	1.399 (3)	C11—N3	1.287 (3)
C1—C2	1.400 (3)	C11—C13	1.482 (3)
C1—C10	1.477 (3)	C11—C12	1.497 (3)
C2—C3	1.368 (3)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.376 (3)	C12—H12C	0.9600
C3—H3	0.9300	C13—C14	1.387 (3)
C4—C5	1.368 (3)	C13—C18	1.391 (3)
C4—H4	0.9300	C14—C15	1.370 (3)
C5—C6	1.393 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.375 (3)
C6—N1	1.416 (3)	C15—H15	0.9300
C7—C8	1.456 (5)	C16—C17	1.391 (3)
C7—N1	1.493 (3)	C16—C19	1.505 (3)
C7—H7A	0.9700	C17—C18	1.377 (3)
C7—H7B	0.9700	C17—H17	0.9300
C8—H8A	0.9600	C18—H18	0.9300
C8—H8B	0.9600	C19—H19A	0.9600
C8—H8C	0.9600	C19—H19B	0.9600
C9—C10	1.509 (3)	C19—H19C	0.9600
C9—S1	1.742 (2)	S1—O1	1.4135 (19)
C9—H9A	0.9700	S1—O2	1.4233 (17)
C9—H9B	0.9700	S1—N1	1.643 (2)
C10—N2	1.282 (3)	N2—N3	1.397 (2)

C6—C1—C2	118.04 (19)	C11—C12—H12A	109.5
C6—C1—C10	122.43 (18)	C11—C12—H12B	109.5
C2—C1—C10	119.52 (19)	H12A—C12—H12B	109.5
C3—C2—C1	121.9 (2)	C11—C12—H12C	109.5
C3—C2—H2	119.1	H12A—C12—H12C	109.5
C1—C2—H2	119.1	H12B—C12—H12C	109.5
C2—C3—C4	119.6 (2)	C14—C13—C18	117.4 (2)
C2—C3—H3	120.2	C14—C13—C11	121.6 (2)
C4—C3—H3	120.2	C18—C13—C11	120.97 (19)
C5—C4—C3	120.0 (2)	C15—C14—C13	121.4 (2)
C5—C4—H4	120.0	C15—C14—H14	119.3
C3—C4—H4	120.0	C13—C14—H14	119.3
C4—C5—C6	121.4 (2)	C14—C15—C16	121.5 (2)
C4—C5—H5	119.3	C14—C15—H15	119.3
C6—C5—H5	119.3	C16—C15—H15	119.3
C5—C6—C1	119.1 (2)	C15—C16—C17	117.7 (2)
C5—C6—N1	120.1 (2)	C15—C16—C19	120.9 (2)
C1—C6—N1	120.82 (18)	C17—C16—C19	121.4 (2)
C8—C7—N1	112.2 (3)	C18—C17—C16	121.2 (2)
C8—C7—H7A	109.2	C18—C17—H17	119.4
N1—C7—H7A	109.2	C16—C17—H17	119.4
C8—C7—H7B	109.2	C17—C18—C13	120.9 (2)
N1—C7—H7B	109.2	C17—C18—H18	119.6
H7A—C7—H7B	107.9	C13—C18—H18	119.6
C7—C8—H8A	109.5	C16—C19—H19A	109.5
C7—C8—H8B	109.5	C16—C19—H19B	109.5
H8A—C8—H8B	109.5	H19A—C19—H19B	109.5
C7—C8—H8C	109.5	C16—C19—H19C	109.5
H8A—C8—H8C	109.5	H19A—C19—H19C	109.5
H8B—C8—H8C	109.5	H19B—C19—H19C	109.5
C10—C9—S1	110.92 (14)	O1—S1—O2	118.78 (12)
C10—C9—H9A	109.5	O1—S1—N1	110.96 (11)
S1—C9—H9A	109.5	O2—S1—N1	106.91 (11)
C10—C9—H9B	109.5	O1—S1—C9	107.98 (12)
S1—C9—H9B	109.5	O2—S1—C9	110.88 (10)
H9A—C9—H9B	108.0	N1—S1—C9	99.65 (11)
N2—C10—C1	117.42 (19)	C6—N1—C7	121.4 (2)
N2—C10—C9	123.51 (19)	C6—N1—S1	117.47 (16)
C1—C10—C9	119.07 (18)	C7—N1—S1	119.90 (17)
N3—C11—C13	115.83 (19)	C10—N2—N3	113.76 (18)
N3—C11—C12	124.8 (2)	C11—N3—N2	113.78 (19)
C13—C11—C12	119.40 (19)

C6—C1—C2—C3	−0.8 (3)	C15—C16—C17—C18	−1.1 (3)
C10—C1—C2—C3	177.9 (2)	C19—C16—C17—C18	178.7 (2)
C1—C2—C3—C4	−0.2 (4)	C16—C17—C18—C13	0.3 (3)
C2—C3—C4—C5	1.0 (4)	C14—C13—C18—C17	0.5 (3)
C3—C4—C5—C6	−0.8 (4)	C11—C13—C18—C17	−179.7 (2)
C4—C5—C6—C1	−0.3 (4)	C10—C9—S1—O1	61.17 (18)
C4—C5—C6—N1	178.5 (2)	C10—C9—S1—O2	−167.11 (16)
C2—C1—C6—C5	1.1 (3)	C10—C9—S1—N1	−54.73 (18)
C10—C1—C6—C5	−177.7 (2)	C5—C6—N1—C7	−19.6 (4)
C2—C1—C6—N1	−177.7 (2)	C1—C6—N1—C7	159.1 (2)
C10—C1—C6—N1	3.6 (3)	C5—C6—N1—S1	147.7 (2)
C6—C1—C10—N2	173.5 (2)	C1—C6—N1—S1	−33.5 (3)
C2—C1—C10—N2	−5.2 (3)	C8—C7—N1—C6	92.8 (3)
C6—C1—C10—C9	−6.5 (3)	C8—C7—N1—S1	−74.3 (3)
C2—C1—C10—C9	174.75 (19)	O1—S1—N1—C6	−57.8 (2)
S1—C9—C10—N2	−144.76 (19)	O2—S1—N1—C6	171.25 (17)
S1—C9—C10—C1	35.3 (2)	C9—S1—N1—C6	55.80 (19)
N3—C11—C13—C14	−167.5 (2)	O1—S1—N1—C7	109.8 (2)
C12—C11—C13—C14	13.1 (3)	O2—S1—N1—C7	−21.2 (2)
N3—C11—C13—C18	12.7 (3)	C9—S1—N1—C7	−136.6 (2)
C12—C11—C13—C18	−166.7 (2)	C1—C10—N2—N3	−179.62 (17)
C18—C13—C14—C15	−0.7 (3)	C9—C10—N2—N3	0.4 (3)
C11—C13—C14—C15	179.6 (2)	C13—C11—N3—N2	−178.06 (18)
C13—C14—C15—C16	−0.1 (4)	C12—C11—N3—N2	1.3 (3)
C14—C15—C16—C17	1.0 (4)	C10—N2—N3—C11	177.98 (19)
C14—C15—C16—C19	−178.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2ⁱ	0.97	2.50	3.402 (4)	155
C9—H9A···Cg3ⁱⁱ	0.97	2.67	3.613 (2)	165

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁N₃O₂S
M_r	355.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	15.9018 (10), 7.3716 (4), 16.8376 (10)
β (°)	111.644 (3)
V (Å³)	1834.57 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.34 × 0.26 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.937, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	14168, 3597, 2598
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.139, 1.02
No. of reflections	3597
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.40

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2ⁱ	0.97	2.50	3.402 (4)	155
C9—H9A···Cg3ⁱⁱ	0.97	2.67	3.613 (2)	165

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, y−1, z.

Acknowledgements

MS acknowledges the HEC Pakistan for providing a PhD fellowship and the University of Sargodha for the X-ray diffraction facility.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011b). Asian J. Chem. 23, 2101–2106. CAS Google Scholar
Shafiq, M., Tahir, M. N., Harrison, W. T. A., Khan, I. U. & Shafique, S. (2013). Acta Cryst. E69, o165. CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). J. Chilean Chem. Soc. 56, 527–531. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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