organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o983-o984

A triclinic polymorph of N-[4-(4-methyl­benzene­sulfonamido)­phenyl­sulfon­yl]acetamide

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

(Received 3 February 2012; accepted 26 February 2012; online 7 March 2012)

In the asymmetric unit of the title compound, C15H16N2O5S2, there are two symmetry-independent mol­ecules which adopt similar conformations, with dihedral angles between the aromatic rings of 59.30 (8) and 61.81 (8)°, and dihedral angles between acetamide group and the benzene ring of 77.08 (10) and 78.40 (10)°. Each type of mol­ecule forms similar one-dimensional polymeric structures extending along the b axis via N—H⋯O hydrogen bonds. These hydrogen bonds generate two types of centrosymmetric motifs, R22(8) and R22(20). Moreover C—H⋯O inter­actions assemble the mol­ecules into a three-dimensional framework. The crystal structure was determined from a non-merohedral twin [ratio of the twin components = 0.322 (4):0.678 (4)].

Related literature

For a monoclinic polymorph of the title compound, see: Ashfaq et al. (2010[Ashfaq, M., Khan, I. U., Arshad, M. N., Ahmad, H. & Asghar, M. N. (2010). Acta Cryst. E66, o299.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16N2O5S2

  • Mr = 368.42

  • Triclinic, [P \overline 1]

  • a = 9.6722 (3) Å

  • b = 11.9968 (4) Å

  • c = 15.4784 (6) Å

  • α = 82.802 (2)°

  • β = 79.232 (1)°

  • γ = 89.653 (2)°

  • V = 1750.24 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.33 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[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.915, Tmax = 0.938

  • 31011 measured reflections

  • 8382 independent reflections

  • 5598 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.153

  • S = 1.02

  • 8382 reflections

  • 438 parameters

  • H-atom parameters constrained

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O5i 0.86 2.14 2.841 (3) 138
N2—H2A⋯O4ii 0.86 2.06 2.876 (3) 158
N3—H3A⋯O10iii 0.86 2.18 2.859 (3) 136
N4—H4⋯O8iv 0.86 2.05 2.867 (3) 157
C13—H13⋯O2 0.93 2.49 3.062 (4) 120
C22—H22A⋯O6v 0.96 2.59 3.338 (5) 135
C24—H24⋯O6 0.93 2.46 3.026 (4) 119
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+1; (v) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information


Comment top

The title compound (I), (Fig. 1) has been synthesized as a part of the series of sulfonamide derivatives. The aim of our research work is to find the potential sulfonamide derivatives possesing anti-microbial activity. The crystal structure of the monoclinic polymorph of the title compound has been reported earlier by Ashfaq et al. (2010). The molecules in the two polymorphs differ in conformation.

In (I), two molecules in the asymmetric unit are present, which differ from each other geometrically. In one molecule, the toluene group A (C1–C7), benzene ring B (C8–C13) and the acetamide group C (N2/C14/C15/O5) are planar with r. m. s. deviation of 0.0089 Å, 0.0080 Å and 0.0028 Å, respectively. The dihedral angles between A/B, A/C and B/C are 61.81 (8)°, 45.90 (14)° and 77.08 (10)°, respectively. In second molecule, the toluene group D (C16–C22), benzene ring E (C23–C28) and the acetamide group F (N4/C29/C30/O10) are planar with r. m. s. deviation of 0.0116 Å, 0.0066 Å and 0.0006 Å, respectively. The dihedral angles between D/E, D/F and E/F are 59.30 (8)°, 46.10 (14)° and 78.40 (10)°, respectively. The dihedral angle between two aromatic rings in its polymrph (Ashfaq et al., 2010) is 81.33 (6)° compared to 61.81 (8)° and 59.30 (8)°. In both molecules, there exist weak intramolecular H–bonding of C—H···O type (Table 1). Both molecules are dimerized themselves due to intermolecular H-bonding of N—H···O type forming R22(8) ring motifs (Bernstein et al., 1995). The dimers are interliked due to strong N—H···O type of H–bondings (Table 1, Fig. 2) and form R22(20) ring motifs.

Related literature top

For a monoclinic polymorph of the title compound, see: Ashfaq et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

Equal molar ratio of N-[(4-aminophenyl)sulfonyl]acetamide and p-toluene sulfonyl chloride was dissolved in 20 ml distilled water. The solution with pH = 8–9 adjusted using Na2CO3 (1 M) was stirrered at room temperature for 6 h. Progress of the reaction was monitored by the consumption of suspended p-toluene sulfonyl chloride. On completion, pH was adjusted to 2–3 using HCl (2 N). The precipitate formed was filtered, washed with ditilled water and recrystallized from methanol to afford colorless prisms with m.p. 385 K.

Refinement top

The crystal structure was solved from non-merohedral twin with the twin law in the reciprocal space of 0.211, 0.700, 280.000: 1.211, 0.211, 0.000: 0.429, 0.429, 1.000 and the twin component ratio of 0.322 (4)/0.678 (4). In the refinement the HKLF 5 reflection file format in SHELXL was used.

The H-atoms were positioned geometrically (N—H = 0.86 Å, C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl groups and x = 1.2 for all other H-atoms.

Structure description top

The title compound (I), (Fig. 1) has been synthesized as a part of the series of sulfonamide derivatives. The aim of our research work is to find the potential sulfonamide derivatives possesing anti-microbial activity. The crystal structure of the monoclinic polymorph of the title compound has been reported earlier by Ashfaq et al. (2010). The molecules in the two polymorphs differ in conformation.

In (I), two molecules in the asymmetric unit are present, which differ from each other geometrically. In one molecule, the toluene group A (C1–C7), benzene ring B (C8–C13) and the acetamide group C (N2/C14/C15/O5) are planar with r. m. s. deviation of 0.0089 Å, 0.0080 Å and 0.0028 Å, respectively. The dihedral angles between A/B, A/C and B/C are 61.81 (8)°, 45.90 (14)° and 77.08 (10)°, respectively. In second molecule, the toluene group D (C16–C22), benzene ring E (C23–C28) and the acetamide group F (N4/C29/C30/O10) are planar with r. m. s. deviation of 0.0116 Å, 0.0066 Å and 0.0006 Å, respectively. The dihedral angles between D/E, D/F and E/F are 59.30 (8)°, 46.10 (14)° and 78.40 (10)°, respectively. The dihedral angle between two aromatic rings in its polymrph (Ashfaq et al., 2010) is 81.33 (6)° compared to 61.81 (8)° and 59.30 (8)°. In both molecules, there exist weak intramolecular H–bonding of C—H···O type (Table 1). Both molecules are dimerized themselves due to intermolecular H-bonding of N—H···O type forming R22(8) ring motifs (Bernstein et al., 1995). The dimers are interliked due to strong N—H···O type of H–bondings (Table 1, Fig. 2) and form R22(20) ring motifs.

For a monoclinic polymorph of the title compound, see: Ashfaq et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

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
[Figure 1] Fig. 1. View of the title compound with the displacement ellipsoids drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
[Figure 2] Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form dimers forming R22(8) ring motif and dimers are interlinked and complete R22(20) ring motif. The H-atoms not involved in hydrogen bonding have been omitted for clarity.
N-[4-(4-Methylbenzenesulfonamido)phenylsulfonyl]acetamide top
Crystal data top
C15H16N2O5S2Z = 4
Mr = 368.42F(000) = 768
Triclinic, P1Dx = 1.398 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6722 (3) ÅCell parameters from 4587 reflections
b = 11.9968 (4) Åθ = 1.7–25.0°
c = 15.4784 (6) ŵ = 0.33 mm1
α = 82.802 (2)°T = 296 K
β = 79.232 (1)°Prism, colorless
γ = 89.653 (2)°0.35 × 0.25 × 0.22 mm
V = 1750.24 (11) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
8382 independent reflections
Radiation source: fine-focus sealed tube5598 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 7.60 pixels mm-1θmax = 28.3°, θmin = 1.7°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1515
Tmin = 0.915, Tmax = 0.938l = 2020
31011 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0652P)2 + 0.7795P]
where P = (Fo2 + 2Fc2)/3
8382 reflections(Δ/σ)max = 0.001
438 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
C15H16N2O5S2γ = 89.653 (2)°
Mr = 368.42V = 1750.24 (11) Å3
Triclinic, P1Z = 4
a = 9.6722 (3) ÅMo Kα radiation
b = 11.9968 (4) ŵ = 0.33 mm1
c = 15.4784 (6) ÅT = 296 K
α = 82.802 (2)°0.35 × 0.25 × 0.22 mm
β = 79.232 (1)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
8382 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
5598 reflections with I > 2σ(I)
Tmin = 0.915, Tmax = 0.938Rint = 0.028
31011 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.02Δρmax = 0.52 e Å3
8382 reflectionsΔρmin = 0.45 e Å3
438 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
xyzUiso*/Ueq
S11.18463 (8)0.05657 (7)0.15628 (5)0.0535 (3)
S20.84421 (7)0.35232 (5)0.49521 (5)0.0415 (2)
O11.2489 (3)0.0454 (2)0.13292 (16)0.0730 (9)
O21.2545 (2)0.1621 (2)0.12469 (15)0.0698 (8)
O30.70702 (19)0.30834 (16)0.53244 (14)0.0515 (7)
O40.8603 (2)0.46483 (15)0.44956 (14)0.0523 (7)
O50.8812 (2)0.18161 (16)0.64458 (14)0.0585 (7)
N11.1577 (3)0.0404 (2)0.26522 (15)0.0494 (8)
N20.9331 (2)0.35691 (18)0.57571 (15)0.0441 (7)
C11.0166 (3)0.0638 (3)0.12810 (18)0.0500 (9)
C20.9520 (4)0.1664 (3)0.1181 (2)0.0687 (12)
C30.8155 (4)0.1685 (4)0.1015 (3)0.0785 (16)
C40.7443 (4)0.0727 (4)0.0942 (2)0.0710 (14)
C50.8117 (4)0.0286 (4)0.1023 (2)0.0747 (14)
C60.9484 (4)0.0339 (3)0.1193 (2)0.0650 (12)
C70.5962 (4)0.0779 (5)0.0770 (3)0.107 (2)
C81.0824 (3)0.1175 (2)0.31772 (17)0.0423 (8)
C90.9745 (3)0.0768 (2)0.38598 (18)0.0464 (9)
C100.9013 (3)0.1481 (2)0.44060 (19)0.0450 (8)
C110.9352 (3)0.2614 (2)0.42570 (17)0.0380 (8)
C121.0441 (3)0.3032 (2)0.35796 (19)0.0516 (10)
C131.1186 (3)0.2313 (2)0.3047 (2)0.0562 (10)
C140.9428 (3)0.2699 (2)0.64153 (18)0.0447 (9)
C151.0310 (4)0.2954 (3)0.7061 (2)0.0662 (12)
S30.69039 (8)0.54642 (6)0.15666 (5)0.0506 (2)
S40.34505 (7)0.15067 (5)0.49579 (5)0.0415 (2)
O60.7593 (2)0.4488 (2)0.12796 (15)0.0663 (8)
O70.7553 (2)0.65458 (19)0.12984 (16)0.0685 (8)
O80.3612 (2)0.05275 (15)0.45035 (14)0.0517 (7)
O90.20777 (19)0.18511 (16)0.53232 (14)0.0522 (7)
O100.3820 (2)0.27238 (17)0.64627 (14)0.0581 (7)
N30.6647 (3)0.53153 (19)0.26533 (15)0.0473 (8)
N40.4330 (2)0.11853 (18)0.57696 (15)0.0435 (7)
C160.5211 (3)0.5480 (3)0.13051 (18)0.0494 (9)
C170.4500 (4)0.6488 (3)0.1236 (2)0.0664 (12)
C180.3142 (4)0.6490 (4)0.1090 (3)0.0805 (16)
C190.2471 (4)0.5512 (4)0.1003 (2)0.0774 (16)
C200.3210 (4)0.4524 (4)0.1049 (2)0.0762 (14)
C210.4574 (4)0.4491 (3)0.1199 (2)0.0630 (11)
C220.0974 (4)0.5515 (6)0.0856 (3)0.121 (3)
C230.5887 (3)0.4391 (2)0.31887 (17)0.0412 (8)
C240.6247 (3)0.3287 (2)0.3074 (2)0.0533 (10)
C250.5486 (3)0.2412 (2)0.36048 (19)0.0506 (9)
C260.4380 (3)0.2630 (2)0.42648 (17)0.0389 (8)
C270.4030 (3)0.3724 (2)0.43997 (19)0.0457 (8)
C280.4781 (3)0.4596 (2)0.38568 (18)0.0452 (8)
C290.4428 (3)0.1842 (2)0.64282 (18)0.0450 (9)
C300.5321 (4)0.1372 (3)0.7070 (2)0.0655 (11)
H11.191130.018070.291750.0592*
H20.998570.232500.122440.0824*
H2A0.977040.418650.576840.0530*
H30.771090.237180.095040.0937*
H50.765540.094200.096410.0899*
H60.993240.102500.124620.0780*
H7A0.588290.141130.033630.1594*
H7B0.531930.085980.131090.1594*
H7C0.573750.010050.055240.1594*
H90.951040.000570.395120.0557*
H100.829750.120180.487070.0540*
H121.066660.379530.348570.0619*
H131.193020.258700.260040.0675*
H15A1.083420.230200.721700.0989*
H15B0.971420.315990.758330.0989*
H15C1.094870.356480.679740.0989*
H3A0.698790.581850.290840.0568*
H40.476300.055690.578350.0522*
H170.494060.715640.128700.0796*
H180.266610.716460.104980.0965*
H200.277600.386090.097620.0914*
H210.505380.381720.122810.0753*
H22A0.093750.521630.031340.1804*
H22B0.063710.627030.082010.1804*
H22C0.039280.505900.134130.1804*
H240.700380.314170.263840.0640*
H250.571390.167440.352030.0608*
H270.329610.386730.485150.0548*
H280.454440.533310.393870.0542*
H30A0.474640.092060.756060.0981*
H30B0.575260.197600.728200.0981*
H30C0.603860.091640.678050.0981*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0472 (4)0.0611 (5)0.0493 (4)0.0080 (3)0.0011 (3)0.0085 (3)
S20.0363 (3)0.0328 (3)0.0565 (4)0.0002 (3)0.0108 (3)0.0063 (3)
O10.0676 (15)0.0839 (17)0.0679 (15)0.0294 (13)0.0038 (12)0.0259 (12)
O20.0589 (14)0.0778 (16)0.0642 (14)0.0104 (12)0.0028 (11)0.0026 (12)
O30.0348 (10)0.0470 (11)0.0718 (13)0.0029 (8)0.0058 (9)0.0101 (9)
O40.0540 (12)0.0328 (10)0.0723 (13)0.0028 (8)0.0208 (10)0.0016 (9)
O50.0577 (13)0.0408 (11)0.0734 (14)0.0052 (10)0.0097 (10)0.0028 (10)
N10.0536 (14)0.0459 (13)0.0485 (13)0.0113 (11)0.0110 (11)0.0038 (10)
N20.0470 (13)0.0358 (11)0.0512 (13)0.0061 (10)0.0130 (10)0.0056 (10)
C10.0504 (16)0.0572 (18)0.0418 (15)0.0054 (14)0.0056 (12)0.0088 (13)
C20.073 (2)0.063 (2)0.078 (2)0.0111 (18)0.0283 (19)0.0188 (17)
C30.075 (2)0.085 (3)0.086 (3)0.030 (2)0.033 (2)0.026 (2)
C40.057 (2)0.105 (3)0.0506 (19)0.001 (2)0.0073 (15)0.0122 (19)
C50.073 (2)0.085 (3)0.065 (2)0.024 (2)0.0119 (18)0.0052 (19)
C60.074 (2)0.061 (2)0.058 (2)0.0000 (18)0.0095 (17)0.0041 (15)
C70.064 (3)0.174 (5)0.083 (3)0.001 (3)0.019 (2)0.014 (3)
C80.0442 (14)0.0397 (14)0.0443 (14)0.0046 (11)0.0120 (11)0.0054 (11)
C90.0491 (16)0.0327 (13)0.0562 (17)0.0046 (12)0.0066 (13)0.0058 (12)
C100.0404 (14)0.0388 (14)0.0536 (16)0.0057 (11)0.0042 (12)0.0036 (12)
C110.0360 (13)0.0313 (12)0.0484 (15)0.0019 (10)0.0116 (11)0.0057 (10)
C120.0583 (18)0.0345 (14)0.0574 (18)0.0089 (13)0.0008 (14)0.0027 (12)
C130.0577 (18)0.0446 (16)0.0587 (18)0.0117 (14)0.0060 (14)0.0016 (13)
C140.0380 (14)0.0435 (15)0.0500 (16)0.0057 (12)0.0003 (12)0.0076 (12)
C150.067 (2)0.075 (2)0.059 (2)0.0006 (18)0.0183 (16)0.0083 (16)
S30.0428 (4)0.0556 (4)0.0502 (4)0.0075 (3)0.0006 (3)0.0061 (3)
S40.0370 (3)0.0335 (3)0.0558 (4)0.0017 (3)0.0102 (3)0.0105 (3)
O60.0583 (13)0.0745 (15)0.0614 (14)0.0071 (11)0.0061 (10)0.0172 (11)
O70.0567 (13)0.0655 (14)0.0760 (15)0.0230 (11)0.0049 (11)0.0085 (11)
O80.0558 (12)0.0375 (10)0.0670 (13)0.0009 (9)0.0179 (10)0.0167 (9)
O90.0357 (10)0.0473 (11)0.0733 (14)0.0022 (8)0.0071 (9)0.0108 (9)
O100.0561 (12)0.0486 (12)0.0730 (14)0.0048 (10)0.0105 (10)0.0238 (10)
N30.0508 (14)0.0434 (12)0.0499 (13)0.0085 (10)0.0123 (10)0.0094 (10)
N40.0463 (12)0.0333 (11)0.0522 (13)0.0067 (10)0.0115 (10)0.0075 (9)
C160.0480 (16)0.0589 (18)0.0405 (15)0.0075 (14)0.0046 (12)0.0086 (12)
C170.065 (2)0.067 (2)0.073 (2)0.0022 (18)0.0188 (17)0.0230 (17)
C180.064 (2)0.106 (3)0.080 (3)0.019 (2)0.0204 (19)0.035 (2)
C190.0507 (19)0.136 (4)0.0482 (19)0.011 (2)0.0060 (15)0.026 (2)
C200.074 (2)0.098 (3)0.056 (2)0.042 (2)0.0102 (18)0.0086 (19)
C210.069 (2)0.065 (2)0.0556 (19)0.0159 (17)0.0133 (16)0.0063 (15)
C220.057 (2)0.232 (7)0.084 (3)0.010 (3)0.017 (2)0.058 (4)
C230.0421 (14)0.0379 (13)0.0457 (15)0.0003 (11)0.0125 (11)0.0075 (11)
C240.0525 (17)0.0449 (16)0.0581 (18)0.0098 (13)0.0056 (14)0.0136 (13)
C250.0606 (18)0.0347 (14)0.0553 (17)0.0108 (13)0.0033 (14)0.0128 (12)
C260.0360 (13)0.0343 (13)0.0486 (15)0.0025 (10)0.0110 (11)0.0093 (11)
C270.0389 (14)0.0419 (14)0.0550 (16)0.0079 (12)0.0007 (12)0.0139 (12)
C280.0471 (15)0.0337 (13)0.0550 (16)0.0065 (11)0.0063 (12)0.0121 (11)
C290.0403 (14)0.0422 (15)0.0499 (16)0.0041 (12)0.0003 (12)0.0084 (12)
C300.067 (2)0.078 (2)0.0555 (19)0.0052 (18)0.0188 (16)0.0127 (16)
Geometric parameters (Å, º) top
S1—O11.425 (3)C3—H30.9300
S1—O21.425 (2)C5—H50.9300
S1—N11.644 (2)C6—H60.9300
S1—C11.759 (3)C7—H7A0.9600
S2—O31.421 (2)C7—H7B0.9600
S2—O41.438 (2)C7—H7C0.9600
S2—N21.647 (2)C9—H90.9300
S2—C111.747 (3)C10—H100.9300
S3—O71.424 (2)C12—H120.9300
S3—N31.641 (2)C13—H130.9300
S3—O61.423 (2)C15—H15C0.9600
S3—C161.758 (3)C15—H15B0.9600
S4—O91.423 (2)C15—H15A0.9600
S4—N41.651 (2)C16—C171.390 (5)
S4—O81.436 (2)C16—C211.382 (5)
S4—C261.751 (3)C17—C181.374 (6)
O5—C141.210 (3)C18—C191.378 (7)
O10—C291.209 (3)C19—C201.382 (6)
N1—C81.416 (4)C19—C221.507 (6)
N2—C141.380 (3)C20—C211.381 (6)
N1—H10.8600C23—C281.386 (4)
N2—H2A0.8600C23—C241.392 (3)
N3—C231.417 (4)C24—C251.373 (4)
N4—C291.381 (3)C25—C261.383 (4)
N3—H3A0.8600C26—C271.385 (3)
N4—H40.8600C27—C281.374 (4)
C1—C61.382 (5)C29—C301.492 (5)
C1—C21.382 (5)C17—H170.9300
C2—C31.391 (6)C18—H180.9300
C3—C41.371 (6)C20—H200.9300
C4—C51.379 (7)C21—H210.9300
C4—C71.505 (6)C22—H22A0.9600
C5—C61.395 (5)C22—H22B0.9600
C8—C131.392 (3)C22—H22C0.9600
C8—C91.382 (4)C24—H240.9300
C9—C101.378 (4)C25—H250.9300
C10—C111.381 (3)C27—H270.9300
C11—C121.387 (4)C28—H280.9300
C12—C131.375 (4)C30—H30A0.9600
C14—C151.490 (5)C30—H30B0.9600
C2—H20.9300C30—H30C0.9600
O1—S1—O2120.70 (15)C4—C7—H7B110.00
O1—S1—N1104.06 (14)C4—C7—H7C110.00
O1—S1—C1109.20 (17)C4—C7—H7A109.00
O2—S1—N1108.23 (14)H7B—C7—H7C109.00
O2—S1—C1107.86 (15)C8—C9—H9120.00
N1—S1—C1105.84 (14)C10—C9—H9120.00
O3—S2—O4119.35 (12)C11—C10—H10120.00
O3—S2—N2108.69 (12)C9—C10—H10120.00
O3—S2—C11110.10 (13)C13—C12—H12120.00
O4—S2—N2103.10 (12)C11—C12—H12120.00
O4—S2—C11108.62 (12)C8—C13—H13120.00
N2—S2—C11106.04 (12)C12—C13—H13120.00
N3—S3—C16105.24 (14)C14—C15—H15C109.00
O7—S3—C16109.50 (15)H15B—C15—H15C110.00
O6—S3—N3107.70 (13)C14—C15—H15A109.00
O6—S3—C16108.13 (15)H15A—C15—H15B110.00
O6—S3—O7120.60 (14)H15A—C15—H15C110.00
O7—S3—N3104.61 (14)C14—C15—H15B109.00
O8—S4—C26108.63 (12)S3—C16—C17119.5 (3)
O9—S4—N4108.81 (12)S3—C16—C21120.2 (3)
O8—S4—N4102.93 (12)C17—C16—C21120.3 (3)
O8—S4—O9119.59 (12)C16—C17—C18119.6 (4)
O9—S4—C26109.97 (13)C17—C18—C19121.3 (4)
N4—S4—C26105.93 (12)C18—C19—C22121.2 (5)
S1—N1—C8123.5 (2)C20—C19—C22120.6 (5)
S2—N2—C14125.40 (18)C18—C19—C20118.2 (4)
C8—N1—H1118.00C19—C20—C21122.0 (4)
S1—N1—H1118.00C16—C21—C20118.6 (4)
S2—N2—H2A117.00C24—C23—C28119.4 (2)
C14—N2—H2A117.00N3—C23—C24121.6 (2)
S3—N3—C23122.68 (19)N3—C23—C28119.0 (2)
S4—N4—C29125.40 (18)C23—C24—C25120.0 (3)
C23—N3—H3A119.00C24—C25—C26119.9 (2)
S3—N3—H3A119.00S4—C26—C25119.41 (19)
C29—N4—H4117.00S4—C26—C27119.8 (2)
S4—N4—H4117.00C25—C26—C27120.7 (2)
C2—C1—C6120.6 (3)C26—C27—C28119.1 (3)
S1—C1—C6119.6 (3)C23—C28—C27120.8 (2)
S1—C1—C2119.8 (3)O10—C29—C30124.3 (3)
C1—C2—C3118.4 (4)N4—C29—C30114.7 (2)
C2—C3—C4122.2 (4)O10—C29—N4121.0 (3)
C3—C4—C5118.6 (4)C16—C17—H17120.00
C5—C4—C7120.6 (4)C18—C17—H17120.00
C3—C4—C7120.8 (4)C17—C18—H18119.00
C4—C5—C6120.8 (4)C19—C18—H18119.00
C1—C6—C5119.4 (4)C19—C20—H20119.00
C9—C8—C13119.7 (2)C21—C20—H20119.00
N1—C8—C13121.7 (3)C16—C21—H21121.00
N1—C8—C9118.5 (2)C20—C21—H21121.00
C8—C9—C10120.6 (2)C19—C22—H22A109.00
C9—C10—C11119.4 (3)C19—C22—H22B110.00
S2—C11—C12119.58 (19)C19—C22—H22C109.00
S2—C11—C10119.7 (2)H22A—C22—H22B109.00
C10—C11—C12120.6 (2)H22A—C22—H22C109.00
C11—C12—C13119.7 (2)H22B—C22—H22C109.00
C8—C13—C12119.9 (3)C23—C24—H24120.00
N2—C14—C15114.8 (2)C25—C24—H24120.00
O5—C14—C15124.7 (3)C24—C25—H25120.00
O5—C14—N2120.5 (3)C26—C25—H25120.00
C1—C2—H2121.00C26—C27—H27120.00
C3—C2—H2121.00C28—C27—H27120.00
C4—C3—H3119.00C23—C28—H28120.00
C2—C3—H3119.00C27—C28—H28120.00
C4—C5—H5120.00C29—C30—H30A109.00
C6—C5—H5120.00C29—C30—H30B109.00
C1—C6—H6120.00C29—C30—H30C109.00
C5—C6—H6120.00H30A—C30—H30B109.00
H7A—C7—H7C109.00H30A—C30—H30C109.00
H7A—C7—H7B109.00H30B—C30—H30C109.00
O1—S1—N1—C8173.5 (3)S4—N4—C29—O101.7 (4)
O2—S1—N1—C857.0 (3)S4—N4—C29—C30178.4 (2)
C1—S1—N1—C858.4 (3)C2—C1—C6—C51.6 (4)
O1—S1—C1—C2159.9 (2)S1—C1—C2—C3175.9 (3)
O1—S1—C1—C622.5 (3)C6—C1—C2—C31.8 (5)
O2—S1—C1—C227.0 (3)S1—C1—C6—C5176.1 (2)
O2—S1—C1—C6155.3 (2)C1—C2—C3—C40.5 (6)
N1—S1—C1—C288.7 (3)C2—C3—C4—C51.0 (6)
N1—S1—C1—C689.0 (3)C2—C3—C4—C7179.5 (4)
O3—S2—N2—C1448.6 (2)C7—C4—C5—C6179.2 (3)
O4—S2—N2—C14176.2 (2)C3—C4—C5—C61.3 (5)
C11—S2—N2—C1469.7 (2)C4—C5—C6—C10.0 (5)
O3—S2—C11—C1027.0 (3)N1—C8—C13—C12179.1 (3)
O3—S2—C11—C12155.3 (2)C13—C8—C9—C100.8 (4)
O4—S2—C11—C10159.3 (2)N1—C8—C9—C10177.9 (3)
O4—S2—C11—C1222.9 (3)C9—C8—C13—C122.0 (4)
N2—S2—C11—C1090.4 (3)C8—C9—C10—C111.0 (4)
N2—S2—C11—C1287.3 (2)C9—C10—C11—S2179.4 (2)
N3—S3—C16—C1786.6 (3)C9—C10—C11—C121.6 (4)
N3—S3—C16—C2191.3 (3)S2—C11—C12—C13178.2 (2)
O6—S3—N3—C2357.2 (3)C10—C11—C12—C130.4 (4)
O7—S3—N3—C23173.4 (2)C11—C12—C13—C81.4 (4)
C16—S3—N3—C2358.0 (3)S3—C16—C17—C18175.7 (3)
O6—S3—C16—C17158.6 (2)C21—C16—C17—C182.1 (5)
O6—S3—C16—C2123.6 (3)S3—C16—C21—C20176.0 (2)
O7—S3—C16—C1725.4 (3)C17—C16—C21—C201.8 (4)
O7—S3—C16—C21156.8 (2)C16—C17—C18—C190.5 (6)
O8—S4—N4—C29176.4 (2)C17—C18—C19—C201.3 (6)
O9—S4—N4—C2948.6 (2)C17—C18—C19—C22179.1 (4)
C26—S4—N4—C2969.6 (2)C18—C19—C20—C211.6 (5)
O8—S4—C26—C2523.8 (3)C22—C19—C20—C21178.8 (3)
O8—S4—C26—C27158.2 (2)C19—C20—C21—C160.0 (5)
O9—S4—C26—C25156.4 (2)N3—C23—C24—C25180.0 (3)
O9—S4—C26—C2725.6 (3)C28—C23—C24—C251.7 (4)
N4—S4—C26—C2586.2 (2)N3—C23—C28—C27179.0 (3)
N4—S4—C26—C2791.9 (2)C24—C23—C28—C270.6 (4)
S1—N1—C8—C9128.8 (3)C23—C24—C25—C261.3 (4)
S1—N1—C8—C1354.2 (4)C24—C25—C26—S4178.2 (2)
S2—N2—C14—C15179.5 (2)C24—C25—C26—C270.2 (4)
S2—N2—C14—O51.4 (4)S4—C26—C27—C28179.2 (2)
S3—N3—C23—C28127.2 (3)C25—C26—C27—C281.2 (4)
S3—N3—C23—C2454.5 (4)C26—C27—C28—C230.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.862.142.841 (3)138
N2—H2A···O4ii0.862.062.876 (3)158
N3—H3A···O10iii0.862.182.859 (3)136
N4—H4···O8iv0.862.052.867 (3)157
C13—H13···O20.932.493.062 (4)120
C22—H22A···O6v0.962.593.338 (5)135
C24—H24···O60.932.463.026 (4)119
Symmetry codes: (i) x+2, y, z+1; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y, z+1; (v) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H16N2O5S2
Mr368.42
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.6722 (3), 11.9968 (4), 15.4784 (6)
α, β, γ (°)82.802 (2), 79.232 (1), 89.653 (2)
V3)1750.24 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.35 × 0.25 × 0.22
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.915, 0.938
No. of measured, independent and
observed [I > 2σ(I)] reflections
31011, 8382, 5598
Rint0.028
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.153, 1.02
No. of reflections8382
No. of parameters438
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.52, 0.45

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···AD—HH···AD···AD—H···A
N1—H1···O5i0.862.142.841 (3)138
N2—H2A···O4ii0.862.062.876 (3)158
N3—H3A···O10iii0.862.182.859 (3)136
N4—H4···O8iv0.862.052.867 (3)157
C13—H13···O20.932.493.062 (4)120
C22—H22A···O6v0.962.593.338 (5)135
C24—H24···O60.932.463.026 (4)119
Symmetry codes: (i) x+2, y, z+1; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y, z+1; (v) x+1, y+1, z.
 

Acknowledgements

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

References

First citationAshfaq, M., Khan, I. U., Arshad, M. N., Ahmad, H. & Asghar, M. N. (2010). Acta Cryst. E66, o299.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Pages o983-o984
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