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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-(4-Meth­­oxy­benzene­sulfonamido)­benzoic acid

aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: iukhan@gcu.edu.pk, akkurt@erciyes.edu.tr

(Received 23 June 2011; accepted 26 June 2011; online 30 June 2011)

The asymmetric unit of the title compound, C14H13NO5S, contains two independent mol­ecules in which the dihedral angles between the aromatic rings are 83.45 (11) and 86.65 (9)°. In the crystal, the independent mol­ecules are connected by N—H⋯O and O—H⋯O hydrogen bonds, forming a double-chain structure along [401]. A weak ππ stacking inter­action with a centroid–centroid distance of 3.7509 (13) Å and C—H⋯O hydrogen bonds are also observed.

Related literature

For background to the biological activity of sulfonamides, see: Hanson et al. (1999[Hanson, P. R., Probst, D. A., Robinson, R. E. & Yau, M. (1999). Tetrahedron Lett. 40, 4761-4763.]). For related structures, see: Mustafa et al. (2010[Mustafa, G., Akkurt, M., Khan, I. U., Naseem, R. & Sajjad, B. (2010). Acta Cryst. E66, o1768.], 2011[Mustafa, G., Khan, I. U., Zia-ur-Rehman, M., Sharif, S. & Arshad, M. N. (2011). Acta Cryst. E67, o1018.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13NO5S

  • Mr = 307.32

  • Monoclinic, P 21 /c

  • a = 8.6980 (3) Å

  • b = 21.7471 (8) Å

  • c = 14.5824 (6) Å

  • β = 95.153 (2)°

  • V = 2747.21 (18) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 296 K

  • 0.38 × 0.31 × 0.28 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.909, Tmax = 0.931

  • 25188 measured reflections

  • 6806 independent reflections

  • 5475 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.120

  • S = 1.04

  • 6806 reflections

  • 394 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—HN1⋯O8i 0.84 (2) 2.31 (2) 3.122 (2) 165 (2)
O2—HO1⋯O7ii 0.81 (2) 1.78 (2) 2.583 (2) 172 (2)
N2—HN2⋯O3iii 0.82 (2) 2.15 (2) 2.959 (2) 173 (2)
O6—HO2⋯O1iv 0.82 (2) 2.02 (2) 2.8338 (19) 173 (2)
C4—H4⋯O4 0.93 2.54 3.149 (2) 123
C9—H9⋯O7 0.93 2.32 3.224 (3) 165
C13—H13⋯O10v 0.93 2.57 3.381 (3) 146
C14—H14A⋯O8iv 0.96 2.42 3.370 (3) 169
C23—H23⋯O2 0.93 2.52 3.286 (2) 140
C26—H26⋯O1vi 0.93 2.57 3.197 (2) 125
Symmetry codes: (i) x-1, y, z; (ii) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) x+1, y, z; (iv) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (v) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (vi) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Sulfonamides are well known for their various types of biological activities (e.g. Hanson et al., 1999). In the present paper, the structure of the title compound, (I), is reported.

As shown in Fig. 1, the asymmetric unit of the title compound (I) contains two crystallographically independent molecules A (with S1) and B (with S2). All the bond lengths (Allen et al., 1987) and angles are within normal ranges and they are similar to those of the related molecules (Mustafa et al., 2010, 2011). The dihedral angles between the aromatic rings of (I) is 83.45 (11)° for molecule A and 86.65 (9)° for molecule B.

The crystal packing (Fig. 2, Table 1) is stabilized by C—H···O, N—H···O and O—H···O hydrogen bonds and a weak ππ interaction between the benzene rings attached with the methoxy group of the symmetry independent molecules [Cg2···Cg4iv = 3.7509 (13) Å; symmetry code: (iv) x - 1, -y + 1/2, z - 1/2; Cg2 and Cg4 are the centroid of the C8–C13 and C22–C27 benzene rings, respectively].

Related literature top

For background to the biological activity of sulfonamides, see: Hanson et al. (1999). For related structures, see: Mustafa et al. (2010, 2011). For bond-length data, see: Allen et al. (1987).

Experimental top

To a mixture of p-amino benzoic acid (1.0 g, 7.3 mmoles) and distilled water (10 ml) in a round bottomflask (25 ml) 1M aqueous sodium carbonate solution was added to maintain the pH between 8–9. 4-Methoxy benzenesulfonyl chloride (1.51 g, 7.3 mmol) was added to this solution and was kept stirred at room temperature for 5 h. pH of the reaction mixture was adjusted to 1–2, using 1 N HCl and the precipitates obtained were filtered, washed with distilled water, dried and recrystallized from methanol to yield light brown crystals of (I).

Refinement top

Five reflections giving bad agreements with Fc, viz. (110), (100), (020), (021) and (011), were omitted during the final cycles of refinement. The H atoms of the NH and OH groups of the two molecules in the asymmetric unit were located in a difference map and refined with the distance restraints N—H = 0.86 (2) Å and O—H = 0.82 (2) Å. Their isotropic displacement parameters were set to be 1.2Ueq(N) for NH groups and 1.5Ueq(O) for OH groups. The aromatic and methyl H atoms were placed in calculated positions [C—H = 0.93 and 0.96 Å], with Uiso constrained to be 1.5 times Ueq of the carrier atom for the methyl-H and 1.2 times Ueq for the remaining H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing the labelling of all non-H atoms. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound with hydrogen bonds, viewed down a axis. Hydrogen atoms that not involved in the hydrogen-bonding (dashed lines) have been omitted for clarity.
4-(4-Methoxybenzenesulfonamido)benzoic acid top
Crystal data top
C14H13NO5SF(000) = 1280
Mr = 307.32Dx = 1.486 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9988 reflections
a = 8.6980 (3) Åθ = 2.4–28.4°
b = 21.7471 (8) ŵ = 0.26 mm1
c = 14.5824 (6) ÅT = 296 K
β = 95.153 (2)°Block, light brown
V = 2747.21 (18) Å30.38 × 0.31 × 0.28 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer
6806 independent reflections
Radiation source: sealed tube5475 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ϕ and ω scansθmax = 28.4°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker 2007)
h = 1111
Tmin = 0.909, Tmax = 0.931k = 2428
25188 measured reflectionsl = 1419
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0499P)2 + 1.497P]
where P = (Fo2 + 2Fc2)/3
6806 reflections(Δ/σ)max = 0.001
394 parametersΔρmax = 0.45 e Å3
4 restraintsΔρmin = 0.30 e Å3
Crystal data top
C14H13NO5SV = 2747.21 (18) Å3
Mr = 307.32Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.6980 (3) ŵ = 0.26 mm1
b = 21.7471 (8) ÅT = 296 K
c = 14.5824 (6) Å0.38 × 0.31 × 0.28 mm
β = 95.153 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
6806 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker 2007)
5475 reflections with I > 2σ(I)
Tmin = 0.909, Tmax = 0.931Rint = 0.018
25188 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0444 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.45 e Å3
6806 reflectionsΔρmin = 0.30 e Å3
394 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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.24733 (5)0.16859 (2)0.57376 (4)0.0419 (1)
O10.53350 (14)0.11383 (6)0.80744 (9)0.0418 (4)
O20.57070 (16)0.21434 (6)0.79480 (13)0.0606 (5)
O30.36648 (15)0.20947 (6)0.53547 (12)0.0562 (5)
O40.28249 (17)0.12512 (7)0.64187 (11)0.0564 (5)
O50.0035 (3)0.02617 (9)0.27559 (14)0.0870 (8)
N10.11308 (18)0.21531 (7)0.61562 (13)0.0469 (5)
C10.4873 (2)0.16478 (8)0.78203 (12)0.0373 (5)
C20.33184 (19)0.17603 (8)0.73538 (12)0.0349 (5)
C30.2252 (2)0.12892 (8)0.72183 (12)0.0371 (5)
C40.0773 (2)0.14010 (8)0.68239 (13)0.0407 (5)
C50.03454 (19)0.19958 (8)0.65561 (12)0.0361 (5)
C60.1406 (2)0.24698 (8)0.66846 (13)0.0417 (5)
C70.2870 (2)0.23542 (9)0.70806 (14)0.0444 (6)
C80.1707 (2)0.12793 (8)0.48507 (13)0.0396 (5)
C90.1128 (2)0.15868 (9)0.41275 (16)0.0511 (7)
C100.0545 (3)0.12605 (11)0.34123 (16)0.0567 (7)
C110.0575 (3)0.06309 (11)0.34217 (17)0.0599 (8)
C120.1172 (4)0.03327 (11)0.4127 (2)0.0762 (10)
C130.1732 (3)0.06474 (10)0.48410 (17)0.0612 (8)
C140.0691 (3)0.05350 (15)0.20391 (19)0.0827 (10)
S20.65408 (5)0.38949 (2)0.58411 (3)0.0410 (1)
O60.15326 (16)0.40548 (7)0.37226 (11)0.0520 (5)
O70.15559 (17)0.30391 (7)0.37416 (16)0.0794 (7)
O80.79224 (15)0.35378 (7)0.60408 (11)0.0537 (5)
O90.65854 (17)0.44420 (7)0.53070 (11)0.0550 (5)
O100.3728 (2)0.45077 (9)0.92259 (12)0.0764 (7)
N20.53708 (18)0.34000 (7)0.53111 (12)0.0440 (5)
C150.0880 (2)0.35269 (9)0.38936 (14)0.0433 (5)
C160.07422 (19)0.35329 (8)0.42858 (12)0.0369 (5)
C170.1530 (2)0.40609 (8)0.45785 (13)0.0419 (5)
C180.3058 (2)0.40391 (8)0.49278 (14)0.0435 (6)
C190.38196 (19)0.34749 (8)0.49887 (11)0.0347 (5)
C200.3038 (2)0.29444 (8)0.46977 (13)0.0395 (5)
C210.1526 (2)0.29756 (8)0.43499 (14)0.0429 (5)
C220.57550 (19)0.40798 (8)0.68678 (13)0.0375 (5)
C230.5632 (2)0.36265 (8)0.75171 (14)0.0430 (5)
C240.4966 (2)0.37489 (9)0.83181 (14)0.0468 (6)
C250.4431 (2)0.43392 (10)0.84718 (14)0.0496 (6)
C260.4594 (3)0.48007 (9)0.78309 (15)0.0513 (7)
C270.5238 (2)0.46746 (8)0.70259 (14)0.0444 (6)
C280.3489 (4)0.40625 (16)0.9901 (2)0.1000 (14)
HN10.129 (3)0.2526 (7)0.6033 (15)0.0500*
HO10.654 (2)0.2050 (11)0.8197 (16)0.0630*
H30.253400.089100.739500.0450*
H40.006800.108000.673800.0490*
H60.112700.286700.650200.0500*
H70.357300.267600.716800.0530*
H90.112800.201400.411800.0610*
H100.013800.146900.293200.0680*
H120.120100.009500.412600.0910*
H130.212800.043300.531900.0730*
H14A0.004000.078500.167400.1240*
H14B0.107900.022100.166000.1240*
H14C0.153100.078700.229200.1240*
HN20.571 (2)0.3049 (8)0.5344 (15)0.0490*
HO20.245 (2)0.3998 (11)0.3583 (17)0.0610*
H170.102000.443700.453900.0500*
H180.357400.439700.512000.0520*
H200.354200.256700.473900.0470*
H210.101300.261700.415300.0520*
H230.600400.323400.741300.0520*
H240.487400.344100.875200.0560*
H260.426600.519800.794700.0620*
H270.532900.498200.659100.0530*
H28A0.282500.374500.963500.1500*
H28B0.301700.425301.040000.1500*
H28C0.446200.388701.012900.1500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0310 (2)0.0358 (2)0.0574 (3)0.0010 (2)0.0046 (2)0.0053 (2)
O10.0374 (6)0.0350 (6)0.0519 (8)0.0030 (5)0.0018 (5)0.0010 (5)
O20.0371 (7)0.0354 (7)0.1042 (13)0.0012 (6)0.0225 (8)0.0033 (8)
O30.0364 (7)0.0425 (7)0.0860 (11)0.0076 (6)0.0154 (7)0.0127 (7)
O40.0517 (8)0.0546 (9)0.0638 (9)0.0061 (7)0.0110 (7)0.0009 (7)
O50.1154 (16)0.0666 (11)0.0801 (13)0.0167 (11)0.0143 (12)0.0180 (10)
N10.0376 (8)0.0318 (7)0.0680 (11)0.0034 (6)0.0133 (7)0.0069 (7)
C10.0345 (8)0.0343 (8)0.0424 (9)0.0017 (7)0.0001 (7)0.0041 (7)
C20.0330 (8)0.0352 (8)0.0358 (8)0.0011 (6)0.0003 (6)0.0031 (7)
C30.0395 (9)0.0312 (8)0.0399 (9)0.0027 (7)0.0009 (7)0.0030 (7)
C40.0392 (9)0.0318 (8)0.0499 (10)0.0025 (7)0.0032 (7)0.0062 (7)
C50.0335 (8)0.0373 (9)0.0365 (8)0.0020 (7)0.0022 (6)0.0059 (7)
C60.0423 (9)0.0312 (8)0.0500 (10)0.0009 (7)0.0052 (8)0.0028 (7)
C70.0391 (9)0.0354 (9)0.0568 (11)0.0057 (7)0.0061 (8)0.0014 (8)
C80.0355 (8)0.0331 (8)0.0481 (10)0.0000 (7)0.0082 (7)0.0018 (7)
C90.0476 (11)0.0381 (10)0.0661 (13)0.0008 (8)0.0028 (9)0.0036 (9)
C100.0500 (11)0.0632 (14)0.0565 (13)0.0019 (10)0.0026 (9)0.0046 (11)
C110.0631 (13)0.0512 (12)0.0633 (14)0.0103 (10)0.0055 (11)0.0105 (11)
C120.112 (2)0.0380 (12)0.0800 (18)0.0057 (13)0.0163 (16)0.0088 (11)
C130.0842 (16)0.0351 (10)0.0653 (14)0.0013 (10)0.0117 (12)0.0018 (10)
C140.0737 (17)0.108 (2)0.0657 (17)0.0365 (17)0.0026 (13)0.0108 (16)
S20.0325 (2)0.0355 (2)0.0537 (3)0.0009 (2)0.0035 (2)0.0059 (2)
O60.0353 (7)0.0463 (8)0.0725 (10)0.0065 (6)0.0051 (6)0.0095 (7)
O70.0405 (8)0.0438 (8)0.1466 (18)0.0054 (6)0.0317 (9)0.0155 (10)
O80.0321 (6)0.0509 (8)0.0756 (10)0.0035 (6)0.0081 (6)0.0153 (7)
O90.0607 (9)0.0432 (8)0.0621 (9)0.0048 (7)0.0111 (7)0.0019 (7)
O100.1012 (14)0.0737 (11)0.0574 (10)0.0305 (10)0.0240 (9)0.0128 (9)
N20.0356 (8)0.0331 (8)0.0602 (10)0.0064 (6)0.0130 (7)0.0107 (7)
C150.0335 (8)0.0392 (9)0.0564 (11)0.0020 (7)0.0007 (8)0.0085 (8)
C160.0310 (8)0.0389 (9)0.0403 (9)0.0020 (7)0.0004 (7)0.0061 (7)
C170.0392 (9)0.0365 (9)0.0489 (10)0.0081 (7)0.0027 (8)0.0012 (8)
C180.0419 (9)0.0331 (9)0.0532 (11)0.0028 (7)0.0077 (8)0.0069 (8)
C190.0319 (8)0.0375 (9)0.0338 (8)0.0014 (6)0.0020 (6)0.0020 (7)
C200.0347 (8)0.0300 (8)0.0527 (10)0.0043 (6)0.0024 (7)0.0009 (7)
C210.0345 (8)0.0345 (9)0.0583 (11)0.0032 (7)0.0043 (8)0.0023 (8)
C220.0338 (8)0.0303 (8)0.0464 (10)0.0015 (6)0.0078 (7)0.0021 (7)
C230.0412 (9)0.0286 (8)0.0571 (11)0.0022 (7)0.0072 (8)0.0017 (8)
C240.0454 (10)0.0399 (10)0.0534 (11)0.0013 (8)0.0046 (8)0.0109 (8)
C250.0498 (11)0.0488 (11)0.0490 (11)0.0076 (9)0.0020 (9)0.0021 (9)
C260.0661 (13)0.0323 (9)0.0548 (12)0.0104 (9)0.0021 (10)0.0009 (8)
C270.0541 (11)0.0288 (8)0.0494 (11)0.0010 (7)0.0010 (8)0.0017 (7)
C280.110 (2)0.119 (3)0.0770 (19)0.058 (2)0.0408 (18)0.0445 (19)
Geometric parameters (Å, º) top
S1—O31.4395 (15)C3—H30.9300
S1—O41.4242 (16)C4—H40.9300
S1—N11.6249 (17)C6—H60.9300
S1—C81.7475 (19)C7—H70.9300
S2—O81.4385 (15)C9—H90.9300
S2—O91.4245 (16)C10—H100.9300
S2—N21.6279 (17)C12—H120.9300
S2—C221.7476 (19)C13—H130.9300
O1—C11.225 (2)C14—H14A0.9600
O2—C11.303 (2)C14—H14B0.9600
O5—C111.375 (3)C14—H14C0.9600
O5—C141.401 (4)C15—C161.474 (2)
O2—HO10.807 (19)C16—C211.390 (2)
O6—C151.295 (2)C16—C171.385 (2)
O7—C151.223 (2)C17—C181.381 (3)
O10—C251.356 (3)C18—C191.393 (2)
O10—C281.409 (4)C19—C201.386 (2)
O6—HO20.815 (18)C20—C211.368 (3)
N1—C51.404 (2)C22—C271.395 (2)
N1—HN10.839 (16)C22—C231.378 (3)
N2—C191.398 (2)C23—C241.376 (3)
N2—HN20.818 (18)C24—C251.391 (3)
C1—C21.478 (2)C25—C261.387 (3)
C2—C71.397 (3)C26—C271.373 (3)
C2—C31.384 (2)C17—H170.9300
C3—C41.383 (2)C18—H180.9300
C4—C51.392 (2)C20—H200.9300
C5—C61.385 (2)C21—H210.9300
C6—C71.373 (3)C23—H230.9300
C8—C91.382 (3)C24—H240.9300
C8—C131.374 (3)C26—H260.9300
C9—C101.394 (3)C27—H270.9300
C10—C111.370 (3)C28—H28A0.9600
C11—C121.358 (4)C28—H28B0.9600
C12—C131.371 (4)C28—H28C0.9600
O3—S1—O4119.23 (9)C11—C10—H10120.00
O3—S1—N1103.16 (8)C11—C12—H12119.00
O3—S1—C8109.55 (10)C13—C12—H12119.00
O4—S1—N1110.19 (10)C12—C13—H13120.00
O4—S1—C8107.48 (9)C8—C13—H13120.00
N1—S1—C8106.58 (9)H14A—C14—H14C109.00
O9—S2—N2109.83 (9)H14B—C14—H14C109.00
O9—S2—C22107.95 (9)O5—C14—H14A109.00
N2—S2—C22106.44 (8)H14A—C14—H14B109.00
O8—S2—C22109.55 (9)O5—C14—H14B109.00
O8—S2—O9119.89 (9)O5—C14—H14C110.00
O8—S2—N2102.38 (8)O6—C15—O7122.59 (17)
C11—O5—C14119.0 (2)O6—C15—C16117.04 (16)
C1—O2—HO1108.8 (17)O7—C15—C16120.37 (17)
C25—O10—C28119.1 (2)C15—C16—C21117.72 (16)
C15—O6—HO2108.4 (17)C15—C16—C17123.83 (16)
S1—N1—C5127.10 (13)C17—C16—C21118.44 (16)
C5—N1—HN1116.8 (17)C16—C17—C18121.23 (16)
S1—N1—HN1115.1 (17)C17—C18—C19119.35 (16)
S2—N2—C19128.76 (13)C18—C19—C20119.74 (16)
C19—N2—HN2117.4 (13)N2—C19—C18124.27 (16)
S2—N2—HN2112.5 (13)N2—C19—C20115.98 (15)
O1—C1—O2122.80 (16)C19—C20—C21120.06 (16)
O1—C1—C2123.41 (16)C16—C21—C20121.18 (16)
O2—C1—C2113.78 (15)S2—C22—C23118.99 (14)
C3—C2—C7118.51 (16)S2—C22—C27120.76 (14)
C1—C2—C7120.31 (16)C23—C22—C27120.24 (17)
C1—C2—C3121.11 (16)C22—C23—C24120.65 (17)
C2—C3—C4121.04 (16)C23—C24—C25119.21 (18)
C3—C4—C5119.68 (16)O10—C25—C26115.58 (19)
N1—C5—C6116.62 (15)O10—C25—C24124.20 (19)
N1—C5—C4123.66 (16)C24—C25—C26120.22 (19)
C4—C5—C6119.72 (16)C25—C26—C27120.38 (18)
C5—C6—C7120.13 (17)C22—C27—C26119.25 (18)
C2—C7—C6120.92 (17)C16—C17—H17119.00
C9—C8—C13118.86 (19)C18—C17—H17119.00
S1—C8—C13120.45 (16)C17—C18—H18120.00
S1—C8—C9120.63 (14)C19—C18—H18120.00
C8—C9—C10120.45 (19)C19—C20—H20120.00
C9—C10—C11119.5 (2)C21—C20—H20120.00
O5—C11—C10124.7 (2)C16—C21—H21119.00
C10—C11—C12119.6 (2)C20—C21—H21119.00
O5—C11—C12115.7 (2)C22—C23—H23120.00
C11—C12—C13121.5 (2)C24—C23—H23120.00
C8—C13—C12120.0 (2)C23—C24—H24120.00
C4—C3—H3119.00C25—C24—H24120.00
C2—C3—H3120.00C25—C26—H26120.00
C3—C4—H4120.00C27—C26—H26120.00
C5—C4—H4120.00C22—C27—H27120.00
C7—C6—H6120.00C26—C27—H27120.00
C5—C6—H6120.00O10—C28—H28A109.00
C2—C7—H7120.00O10—C28—H28B109.00
C6—C7—H7120.00O10—C28—H28C110.00
C10—C9—H9120.00H28A—C28—H28B110.00
C8—C9—H9120.00H28A—C28—H28C109.00
C9—C10—H10120.00H28B—C28—H28C109.00
O3—S1—N1—C5175.24 (17)N1—C5—C6—C7179.32 (18)
O4—S1—N1—C556.43 (19)C4—C5—C6—C70.5 (3)
C8—S1—N1—C559.89 (19)C5—C6—C7—C20.4 (3)
N1—S1—C8—C956.08 (18)S1—C8—C9—C10178.76 (17)
O3—S1—C8—C954.89 (17)C13—C8—C9—C101.6 (3)
O4—S1—C8—C9174.20 (15)S1—C8—C13—C12178.0 (2)
N1—S1—C8—C13126.77 (18)C9—C8—C13—C120.7 (4)
O3—S1—C8—C13122.27 (18)C8—C9—C10—C111.2 (3)
O4—S1—C8—C138.7 (2)C9—C10—C11—O5180.0 (2)
O8—S2—C22—C2346.00 (17)C9—C10—C11—C120.0 (4)
O8—S2—C22—C27134.90 (15)C10—C11—C12—C130.8 (5)
O9—S2—C22—C23178.14 (14)O5—C11—C12—C13179.2 (3)
N2—S2—C22—C2364.00 (16)C11—C12—C13—C80.5 (4)
C22—S2—N2—C1961.60 (18)O7—C15—C16—C17172.0 (2)
O9—S2—C22—C272.76 (17)O6—C15—C16—C178.0 (3)
N2—S2—C22—C27115.10 (15)O6—C15—C16—C21170.94 (18)
O9—S2—N2—C1955.01 (19)O7—C15—C16—C219.0 (3)
O8—S2—N2—C19176.56 (16)C21—C16—C17—C180.1 (3)
C14—O5—C11—C104.3 (4)C17—C16—C21—C200.4 (3)
C14—O5—C11—C12175.8 (3)C15—C16—C17—C18179.01 (18)
C28—O10—C25—C241.0 (3)C15—C16—C21—C20179.36 (18)
C28—O10—C25—C26178.7 (2)C16—C17—C18—C190.2 (3)
S1—N1—C5—C413.7 (3)C17—C18—C19—C200.1 (3)
S1—N1—C5—C6166.56 (15)C17—C18—C19—N2178.53 (17)
S2—N2—C19—C20169.78 (14)N2—C19—C20—C21178.38 (17)
S2—N2—C19—C1811.7 (3)C18—C19—C20—C210.2 (3)
O1—C1—C2—C7179.84 (17)C19—C20—C21—C160.4 (3)
O2—C1—C2—C3175.85 (17)S2—C22—C27—C26178.50 (16)
O2—C1—C2—C71.0 (3)C23—C22—C27—C260.6 (3)
O1—C1—C2—C33.4 (3)S2—C22—C23—C24177.51 (14)
C3—C2—C7—C60.1 (3)C27—C22—C23—C241.6 (3)
C1—C2—C3—C4176.70 (17)C22—C23—C24—C250.7 (3)
C7—C2—C3—C40.2 (3)C23—C24—C25—C261.1 (3)
C1—C2—C7—C6177.01 (17)C23—C24—C25—O10178.56 (18)
C2—C3—C4—C50.1 (3)O10—C25—C26—C27177.6 (2)
C3—C4—C5—C60.2 (3)C24—C25—C26—C272.2 (3)
C3—C4—C5—N1179.58 (17)C25—C26—C27—C221.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O8i0.84 (2)2.31 (2)3.122 (2)165 (2)
O2—HO1···O7ii0.81 (2)1.78 (2)2.583 (2)172 (2)
N2—HN2···O3iii0.82 (2)2.15 (2)2.959 (2)173 (2)
O6—HO2···O1iv0.82 (2)2.02 (2)2.8338 (19)173 (2)
C4—H4···O40.932.543.149 (2)123
C7—H7···O20.932.392.709 (2)100
C9—H9···O70.932.323.224 (3)165
C13—H13···O40.932.512.883 (3)105
C13—H13···O10v0.932.573.381 (3)146
C14—H14A···O8iv0.962.423.370 (3)169
C23—H23···O20.932.523.286 (2)140
C26—H26···O1vi0.932.573.197 (2)125
C27—H27···O90.932.542.905 (3)104
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x1, y+1/2, z1/2; (v) x, y1/2, z+3/2; (vi) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC14H13NO5S
Mr307.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.6980 (3), 21.7471 (8), 14.5824 (6)
β (°) 95.153 (2)
V3)2747.21 (18)
Z8
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.38 × 0.31 × 0.28
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker 2007)
Tmin, Tmax0.909, 0.931
No. of measured, independent and
observed [I > 2σ(I)] reflections
25188, 6806, 5475
Rint0.018
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.120, 1.04
No. of reflections6806
No. of parameters394
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.45, 0.30

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O8i0.839 (16)2.305 (17)3.122 (2)165 (2)
O2—HO1···O7ii0.807 (19)1.782 (19)2.583 (2)172 (2)
N2—HN2···O3iii0.818 (18)2.145 (17)2.959 (2)173.1 (19)
O6—HO2···O1iv0.815 (18)2.023 (19)2.8338 (19)173 (2)
C4—H4···O40.932.543.149 (2)123
C9—H9···O70.932.323.224 (3)165
C13—H13···O10v0.932.573.381 (3)146
C14—H14A···O8iv0.962.423.370 (3)169
C23—H23···O20.932.523.286 (2)140
C26—H26···O1vi0.932.573.197 (2)125
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x1, y+1/2, z1/2; (v) x, y1/2, z+3/2; (vi) x+1, y+1/2, z+3/2.
 

Acknowledgements

The authors are grateful to Mr Shahzad Shrif for his assistance and the Higher Education Commission (HEC), Pakistan, for financial support under the project to strengthen the Materials Chemistry Laboratory at GCUL.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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First citationMustafa, G., Khan, I. U., Zia-ur-Rehman, M., Sharif, S. & Arshad, M. N. (2011). Acta Cryst. E67, o1018.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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