4-Methyl-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamo­yl]phen­yl}benzene­sulfonamide

Sohail, M.; Asghar, M.N.; Tahir, M.N.; Shafique, M.; Ashfaq, M.

doi:10.1107/S1600536812005260

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o693

doi:10.1107/S1600536812005260

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4-Methyl-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}benzenesulfonamide

Muhammad Sohail,^a Muhammad Nadeem Asghar,^a M. Nawaz Tahir,^b ^* Muhammad Shafique ^c and Muhammad Ashfaq ^d

^aForman Christian College (A Chartered University), Ferozepur Road, Lahore 54600, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, ^cDepartment of Chemistry, GC University, Lahore 54000, Pakistan, and ^dUniversity of Gujrat, Department of Chemistry, Gujrat, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 2 February 2012; accepted 6 February 2012; online 17 February 2012)

In the title compound, C₁₇H₁₇N₃O₅S₂, the dihedral angle between the two benzene rings is 81.27 (8)° and the heterocyclic ring is oriented at 9.1 (2) and 76.01 (9)° with respect to these rings. Molecules are connected via N—H⋯N and N—H⋯O hydrogen bonds, generating an R₂²(8) motif, into chains running along the [001] direction. There is also an intramolecular C—H⋯O hydrogen bond completing an S(6) ring motif. The polymeric chains are interlinked through intermolecular C—H⋯O hydrogen bonds.

Related literature

For a related crystal structure, see: Ashfaq et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₇N₃O₅S₂
M_r = 407.46
Monoclinic, P 2₁ /c
a = 10.6294 (6) Å
b = 12.2394 (7) Å
c = 14.9673 (11) Å
β = 106.863 (2)°
V = 1863.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.915, T_max = 0.938
17943 measured reflections
4629 independent reflections
2488 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.141
S = 1.02
4629 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3ⁱ	0.86	2.04	2.859 (3)	159
N2—H2A⋯O1ⁱⁱ	0.86	2.39	2.979 (3)	127
C2—H2⋯O4ⁱⁱⁱ	0.93	2.42	3.208 (4)	143
C13—H13⋯O2	0.93	2.49	3.134 (3)	126
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005260/gk2455sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005260/gk2455Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005260/gk2455Isup3.cml

checkCIF report

Comment top

The title compound (Fig. 1) has been synthesized as a part of the series of new sulfonamide derivatives. The aim of our research work is to find the potential sulfonamide derivatives possesing anti-microbial activity. The crystal structures of a similar compound, N-[4-(p-toluenesulfonamido)phenylsulfonyl]acetamide (Ashfaq et al., 2010) has already been reported.

In (I), the phenyl rings A (C1–C6), B (C8—C13) and the heterocyclic five- membered ring C (C14/C15/C16/O5/N3) are planar with r. m. s. deviation of 0.0068 Å, 0.0031 Å and 0.0058 Å, respectively. The dihedral angles between A/B, A/C and B/C are 81.27 (8)°, 9.12 (20)° and 76.01 (9)°, respectively. There exist intramolecular hydrogen bond of C—H···O type (Table 1, Fig. 1) forming an S(6) ring motif (Bernstein et al., 1995). There exist intermolecular hydrogen bonds of N—H···N and N—H···O types (Table 1, Fig. 2) due to which the molecules are connected from the ends to form one-dimensional polymeric network along the [0 0 1] direction and complete R₂²(8) ring motifs. The polymeric chains are interlinked through intermolecular hydrogen bond of C—H···O type (Table 1, Fig. 2).

Related literature top

For a related crystal structure, see: Ashfaq et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

Equimolar amount of 4-amino-N-(5-methyl-4,5-dihydro-1,2-oxazol-3-yl)benzenesulfonamide and p-toluenesulfonyl chloride was dissolved in 20 ml distilled water. The pH was adjusted to 8–9 using Na₂CO₃ (1 M) and the solution was stirred at room temperature for 6 h. The progress of reaction was monitored by the consumption of suspended p-toluenesulfonyl chloride. On completion, pH was adjusted to 2–3 using HCl (2 N). The precipitate formed was filtered, washed with distilled water and recrystallized from methanol to afford colorless prisms (m.p. 403 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecule with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown as small circles of arbitrary radii. The dotted line represents an intramolecular C-H···O hydrogen bond
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric chains extending along [0 0 1] direction.

4-Methyl-N-{4-[(5-methyl-1,2-oxazol-3- yl)sulfamoyl]phenyl}benzenesulfonamide top

Crystal data top

C₁₇H₁₇N₃O₅S₂	F(000) = 848
M_r = 407.46	D_x = 1.452 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2488 reflections
a = 10.6294 (6) Å	θ = 2.2–28.3°
b = 12.2394 (7) Å	µ = 0.32 mm⁻¹
c = 14.9673 (11) Å	T = 296 K
β = 106.863 (2)°	Prism, colorless
V = 1863.5 (2) Å³	0.35 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4629 independent reflections
Radiation source: fine-focus sealed tube	2488 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 7.50 pixels mm^-1	θ_max = 28.3°, θ_min = 2.2°
ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→16
T_min = 0.915, T_max = 0.938	l = −19→19
17943 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0577P)² + 0.1435P] where P = (F_o² + 2F_c²)/3
4629 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₇H₁₇N₃O₅S₂	V = 1863.5 (2) Å³
M_r = 407.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6294 (6) Å	µ = 0.32 mm⁻¹
b = 12.2394 (7) Å	T = 296 K
c = 14.9673 (11) Å	0.35 × 0.25 × 0.22 mm
β = 106.863 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4629 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2488 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.938	R_int = 0.056
17943 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.02	Δρ_max = 0.47 e Å⁻³
4629 reflections	Δρ_min = −0.37 e Å⁻³
246 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S1	0.17178 (7)	0.12476 (6)	0.43330 (5)	0.0475 (3)
S2	0.42023 (7)	0.58034 (6)	0.24478 (5)	0.0485 (3)
O1	0.20899 (18)	0.03512 (15)	0.49755 (15)	0.0596 (8)
O2	0.09435 (18)	0.10311 (16)	0.33965 (14)	0.0575 (7)
O3	0.54004 (19)	0.62547 (15)	0.30218 (14)	0.0594 (7)
O4	0.30436 (19)	0.64578 (16)	0.21489 (15)	0.0642 (8)
O5	0.65024 (19)	0.33654 (16)	0.10010 (15)	0.0618 (8)
N1	0.3101 (2)	0.18092 (19)	0.43406 (16)	0.0519 (8)
N2	0.4456 (2)	0.53685 (18)	0.14776 (16)	0.0486 (8)
N3	0.5291 (2)	0.3918 (2)	0.08307 (18)	0.0605 (9)
C1	0.0863 (2)	0.2224 (2)	0.47933 (18)	0.0398 (8)
C2	−0.0473 (3)	0.2308 (3)	0.4409 (2)	0.0573 (11)
C3	−0.1174 (3)	0.3048 (3)	0.4774 (2)	0.0684 (14)
C4	−0.0567 (3)	0.3690 (3)	0.5522 (2)	0.0615 (12)
C5	0.0766 (4)	0.3572 (3)	0.5909 (3)	0.0703 (14)
C6	0.1495 (3)	0.2850 (3)	0.5556 (2)	0.0592 (11)
C7	−0.1339 (4)	0.4484 (3)	0.5932 (3)	0.1003 (19)
C8	0.3303 (2)	0.2762 (2)	0.38676 (19)	0.0440 (9)
C9	0.4465 (3)	0.3330 (3)	0.4242 (2)	0.0607 (11)
C10	0.4738 (3)	0.4247 (3)	0.3811 (2)	0.0578 (11)
C11	0.3859 (2)	0.4623 (2)	0.30027 (18)	0.0427 (9)
C12	0.2695 (3)	0.4061 (2)	0.2627 (2)	0.0509 (10)
C13	0.2425 (3)	0.3132 (2)	0.3054 (2)	0.0513 (10)
C14	0.5480 (3)	0.4644 (2)	0.14888 (19)	0.0430 (9)
C15	0.6744 (3)	0.4591 (2)	0.2104 (2)	0.0498 (10)
C16	0.7342 (3)	0.3799 (2)	0.1768 (2)	0.0482 (10)
C17	0.8701 (3)	0.3364 (3)	0.2031 (2)	0.0661 (11)
H1	0.37992	0.14872	0.46739	0.0623*
H2	−0.09040	0.18700	0.39052	0.0687*
H2A	0.39496	0.55907	0.09507	0.0583*
H3	−0.20773	0.31110	0.45045	0.0821*
H5	0.11898	0.39923	0.64258	0.0842*
H6	0.23972	0.27863	0.58283	0.0707*
H7A	−0.22555	0.42985	0.57205	0.1503*
H7B	−0.12163	0.52121	0.57344	0.1503*
H7C	−0.10358	0.44443	0.66009	0.1503*
H9	0.50638	0.30849	0.47898	0.0729*
H10	0.55227	0.46190	0.40663	0.0696*
H12	0.20926	0.43125	0.20833	0.0610*
H13	0.16469	0.27516	0.27928	0.0614*
H15	0.70953	0.50155	0.26337	0.0597*
H17A	0.90803	0.34876	0.15310	0.0992*
H17B	0.86837	0.25935	0.21492	0.0992*
H17C	0.92184	0.37272	0.25840	0.0992*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0381 (4)	0.0495 (4)	0.0522 (5)	0.0024 (3)	0.0088 (3)	−0.0024 (4)
S2	0.0440 (4)	0.0468 (4)	0.0504 (5)	0.0060 (3)	0.0071 (3)	−0.0020 (3)
O1	0.0506 (12)	0.0490 (12)	0.0743 (15)	0.0042 (10)	0.0104 (10)	0.0135 (11)
O2	0.0497 (11)	0.0649 (13)	0.0521 (13)	0.0017 (10)	0.0054 (10)	−0.0180 (10)
O3	0.0567 (12)	0.0535 (12)	0.0586 (14)	−0.0064 (10)	0.0019 (11)	−0.0103 (10)
O4	0.0588 (13)	0.0586 (13)	0.0694 (15)	0.0221 (11)	0.0095 (11)	0.0017 (11)
O5	0.0484 (12)	0.0645 (13)	0.0666 (15)	0.0060 (11)	0.0075 (11)	−0.0149 (11)
N1	0.0332 (12)	0.0610 (15)	0.0591 (16)	0.0086 (11)	0.0097 (11)	0.0108 (13)
N2	0.0456 (13)	0.0547 (14)	0.0425 (14)	0.0071 (12)	0.0083 (11)	0.0061 (11)
N3	0.0435 (14)	0.0665 (17)	0.0629 (18)	0.0073 (13)	0.0018 (13)	−0.0123 (14)
C1	0.0350 (14)	0.0425 (15)	0.0391 (15)	−0.0024 (12)	0.0063 (12)	−0.0003 (12)
C2	0.0443 (16)	0.074 (2)	0.0498 (19)	0.0014 (16)	0.0076 (14)	−0.0161 (16)
C3	0.0527 (19)	0.087 (3)	0.065 (2)	0.0168 (18)	0.0165 (17)	−0.005 (2)
C4	0.073 (2)	0.058 (2)	0.062 (2)	0.0090 (18)	0.0330 (19)	0.0019 (17)
C5	0.082 (3)	0.063 (2)	0.065 (2)	−0.014 (2)	0.020 (2)	−0.0241 (18)
C6	0.0465 (16)	0.066 (2)	0.059 (2)	−0.0070 (16)	0.0059 (15)	−0.0122 (17)
C7	0.128 (4)	0.084 (3)	0.105 (3)	0.030 (3)	0.059 (3)	−0.007 (2)
C8	0.0335 (14)	0.0518 (17)	0.0465 (17)	0.0084 (14)	0.0113 (13)	−0.0003 (14)
C9	0.0451 (17)	0.071 (2)	0.053 (2)	−0.0002 (16)	−0.0063 (15)	0.0160 (17)
C10	0.0416 (16)	0.068 (2)	0.054 (2)	−0.0052 (16)	−0.0018 (14)	0.0076 (17)
C11	0.0353 (14)	0.0511 (16)	0.0409 (16)	0.0056 (13)	0.0098 (12)	−0.0021 (13)
C12	0.0399 (16)	0.0602 (19)	0.0451 (17)	0.0064 (15)	0.0007 (14)	0.0041 (15)
C13	0.0353 (14)	0.061 (2)	0.0507 (18)	−0.0007 (14)	0.0017 (13)	−0.0019 (16)
C14	0.0414 (16)	0.0438 (16)	0.0438 (16)	−0.0055 (14)	0.0126 (13)	0.0034 (14)
C15	0.0392 (15)	0.0574 (19)	0.0480 (17)	−0.0066 (14)	0.0052 (14)	−0.0071 (15)
C16	0.0384 (15)	0.0499 (17)	0.0537 (19)	−0.0048 (14)	0.0094 (14)	0.0042 (15)
C17	0.0455 (17)	0.067 (2)	0.083 (2)	0.0075 (16)	0.0141 (17)	−0.0025 (18)

Geometric parameters (Å, º) top

S1—O1	1.437 (2)	C8—C9	1.386 (4)
S1—O2	1.429 (2)	C9—C10	1.367 (5)
S1—N1	1.620 (2)	C10—C11	1.376 (4)
S1—C1	1.758 (3)	C11—C12	1.384 (4)
S2—O3	1.425 (2)	C12—C13	1.375 (4)
S2—O4	1.428 (2)	C14—C15	1.393 (4)
S2—N2	1.641 (2)	C15—C16	1.335 (4)
S2—C11	1.757 (3)	C16—C17	1.482 (5)
O5—N3	1.411 (3)	C2—H2	0.9300
O5—C16	1.342 (4)	C3—H3	0.9300
N1—C8	1.413 (3)	C5—H5	0.9300
N2—C14	1.400 (4)	C6—H6	0.9300
N3—C14	1.298 (4)	C7—H7A	0.9600
N1—H1	0.8600	C7—H7B	0.9600
N2—H2A	0.8600	C7—H7C	0.9600
C1—C2	1.373 (4)	C9—H9	0.9300
C1—C6	1.377 (4)	C10—H10	0.9300
C2—C3	1.382 (5)	C12—H12	0.9300
C3—C4	1.367 (4)	C13—H13	0.9300
C4—C7	1.512 (5)	C15—H15	0.9300
C4—C5	1.374 (5)	C17—H17A	0.9600
C5—C6	1.378 (5)	C17—H17B	0.9600
C8—C13	1.378 (4)	C17—H17C	0.9600

O1—S1—O2	118.90 (12)	C8—C13—C12	120.2 (3)
O1—S1—N1	104.26 (12)	N2—C14—N3	118.4 (3)
O1—S1—C1	109.27 (12)	N2—C14—C15	129.4 (2)
O2—S1—N1	110.41 (12)	N3—C14—C15	112.2 (3)
O2—S1—C1	107.11 (12)	C14—C15—C16	105.0 (3)
N1—S1—C1	106.26 (12)	O5—C16—C17	116.1 (2)
O3—S2—O4	120.68 (12)	C15—C16—C17	134.0 (3)
O3—S2—N2	108.17 (12)	O5—C16—C15	109.8 (3)
O3—S2—C11	107.80 (12)	C1—C2—H2	120.00
O4—S2—N2	104.65 (12)	C3—C2—H2	120.00
O4—S2—C11	109.32 (12)	C2—C3—H3	119.00
N2—S2—C11	105.17 (12)	C4—C3—H3	119.00
N3—O5—C16	108.1 (2)	C4—C5—H5	119.00
S1—N1—C8	128.05 (18)	C6—C5—H5	119.00
S2—N2—C14	121.44 (19)	C1—C6—H6	121.00
O5—N3—C14	105.0 (2)	C5—C6—H6	121.00
C8—N1—H1	116.00	C4—C7—H7A	109.00
S1—N1—H1	116.00	C4—C7—H7B	109.00
S2—N2—H2A	119.00	C4—C7—H7C	109.00
C14—N2—H2A	119.00	H7A—C7—H7B	109.00
S1—C1—C6	121.3 (2)	H7A—C7—H7C	109.00
C2—C1—C6	120.2 (3)	H7B—C7—H7C	110.00
S1—C1—C2	118.4 (2)	C8—C9—H9	120.00
C1—C2—C3	119.6 (3)	C10—C9—H9	120.00
C2—C3—C4	121.3 (3)	C9—C10—H10	120.00
C3—C4—C5	118.0 (3)	C11—C10—H10	120.00
C3—C4—C7	121.3 (3)	C11—C12—H12	120.00
C5—C4—C7	120.7 (3)	C13—C12—H12	120.00
C4—C5—C6	122.1 (4)	C8—C13—H13	120.00
C1—C6—C5	118.8 (3)	C12—C13—H13	120.00
N1—C8—C9	117.3 (2)	C14—C15—H15	128.00
N1—C8—C13	123.5 (2)	C16—C15—H15	128.00
C9—C8—C13	119.2 (3)	C16—C17—H17A	110.00
C8—C9—C10	120.5 (3)	C16—C17—H17B	109.00
C9—C10—C11	120.4 (3)	C16—C17—H17C	109.00
S2—C11—C12	120.0 (2)	H17A—C17—H17B	109.00
C10—C11—C12	119.3 (3)	H17A—C17—H17C	110.00
S2—C11—C10	120.6 (2)	H17B—C17—H17C	109.00
C11—C12—C13	120.3 (3)

O1—S1—N1—C8	−176.4 (2)	O5—N3—C14—C15	−1.4 (3)
O2—S1—N1—C8	54.8 (3)	S1—C1—C2—C3	178.3 (2)
C1—S1—N1—C8	−61.0 (3)	C6—C1—C2—C3	2.0 (5)
O1—S1—C1—C2	−106.2 (2)	S1—C1—C6—C5	−177.5 (3)
O1—S1—C1—C6	70.1 (3)	C2—C1—C6—C5	−1.3 (5)
O2—S1—C1—C2	23.9 (3)	C1—C2—C3—C4	−1.0 (5)
O2—S1—C1—C6	−159.9 (2)	C2—C3—C4—C5	−0.6 (5)
N1—S1—C1—C2	141.9 (2)	C2—C3—C4—C7	−178.8 (3)
N1—S1—C1—C6	−41.9 (3)	C3—C4—C5—C6	1.2 (6)
O3—S2—N2—C14	53.7 (2)	C7—C4—C5—C6	179.5 (3)
O4—S2—N2—C14	−176.5 (2)	C4—C5—C6—C1	−0.3 (5)
C11—S2—N2—C14	−61.3 (2)	N1—C8—C9—C10	178.7 (3)
O3—S2—C11—C10	−4.6 (3)	C13—C8—C9—C10	0.1 (5)
O3—S2—C11—C12	175.4 (2)	N1—C8—C13—C12	−179.3 (3)
O4—S2—C11—C10	−137.5 (2)	C9—C8—C13—C12	−0.8 (4)
O4—S2—C11—C12	42.5 (3)	C8—C9—C10—C11	0.4 (5)
N2—S2—C11—C10	110.6 (2)	C9—C10—C11—S2	179.8 (2)
N2—S2—C11—C12	−69.4 (2)	C9—C10—C11—C12	−0.2 (4)
C16—O5—N3—C14	0.7 (3)	S2—C11—C12—C13	179.5 (2)
N3—O5—C16—C15	0.4 (3)	C10—C11—C12—C13	−0.5 (4)
N3—O5—C16—C17	−176.7 (2)	C11—C12—C13—C8	1.0 (4)
S1—N1—C8—C9	154.9 (2)	N2—C14—C15—C16	−176.3 (3)
S1—N1—C8—C13	−26.6 (4)	N3—C14—C15—C16	1.6 (3)
S2—N2—C14—N3	145.2 (2)	C14—C15—C16—O5	−1.1 (3)
S2—N2—C14—C15	−37.0 (4)	C14—C15—C16—C17	175.2 (3)
O5—N3—C14—N2	176.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.86	2.04	2.859 (3)	159
N2—H2A···O1ⁱⁱ	0.86	2.39	2.979 (3)	127
C2—H2···O4ⁱⁱⁱ	0.93	2.42	3.208 (4)	143
C13—H13···O2	0.93	2.49	3.134 (3)	126

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇N₃O₅S₂
M_r	407.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.6294 (6), 12.2394 (7), 14.9673 (11)
β (°)	106.863 (2)
V (Å³)	1863.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.35 × 0.25 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.915, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	17943, 4629, 2488
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.141, 1.02
No. of reflections	4629
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.37

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.86	2.04	2.859 (3)	159
N2—H2A···O1ⁱⁱ	0.86	2.39	2.979 (3)	127
C2—H2···O4ⁱⁱⁱ	0.93	2.42	3.208 (4)	143
C13—H13···O2	0.93	2.49	3.134 (3)	126

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

References

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