7-Benzenesulfonamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid monohydrate

Sharif, S.; Akkurt, M.; Khan, I.U.; Salariya, M.A.; Ahmad, S.

doi:10.1107/S1600536809051769

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o73-o74

doi:10.1107/S1600536809051769

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7-Benzenesulfonamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid monohydrate

Shahzad Sharif,^a Mehmet Akkurt,^b ^* Islam Ullah Khan,^a ‡ Manan Ayub Salariya ^c and Sarfraz Ahmad ^d

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cPharmagen Ltd, Lahore 54000, Pakistan, and ^dPharmagen Ltd., Lahore 54000, Pakistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 11 November 2009; accepted 1 December 2009; online 9 December 2009)

In the title compound, C₁₄H₁₄N₂O₅S₂·H₂O, the six-membered ring fused to the β-lactam unit has a twisted conformation. Weak intramolecular N—H⋯S and C—H⋯O interactions occur. Intermolecular C—H⋯S, N—H⋯O, C—H⋯O and O—H⋯O hydrogen-bonding interactions stabilize the crystal structure, forming a three-dimensional network. Weak C—H⋯π interactions are also present.

Related literature

For the production of 7-amino-deacetoxycephalosporanic acid-like components by direct fermentation, see: Schroen et al. (2000 ). For 7-benzenesulfonamido-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid methanol solvate, see: Mariam et al. (2009 ). For structures with the β-lactam unit, see: Akkurt et al. (2008a ,b ,c ); Baktır et al. (2009 ); Pınar et al. (2006 ); Yalçın et al. (2009 ); Çelik et al. (2009a ,b ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₅S₂·H₂O
M_r = 372.43
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.9535 (7) Å
b = 15.8248 (19) Å
c = 18.411 (2) Å
V = 1734.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
10847 measured reflections
3572 independent reflections
1890 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.109
S = 0.97
3572 reflections
226 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1425 Friedel pairs
Flack parameter: −0.07 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯OW1ⁱ	0.82	1.86	2.663 (6)	166
OW1—HW1⋯O5ⁱⁱ	0.83 (4)	2.14 (5)	2.799 (6)	136 (5)
N2—H2⋯S1	0.86	2.82	3.136 (3)	103
N2—H2⋯O2ⁱⁱⁱ	0.86	2.30	2.846 (4)	122
OW1—HW2⋯O3	0.84 (5)	2.54 (5)	3.135 (6)	129 (5)
C3—H3A⋯O1	0.96	2.22	2.902 (6)	127
C6—H6⋯S1^iv	0.98	2.80	3.756 (4)	165
C8—H8⋯O4ⁱ	0.98	2.30	3.100 (5)	138
C11—H11⋯O3^v	0.93	2.51	3.192 (6)	130
C3—H3B⋯Cg3ⁱⁱ	0.96	2.72	3.640 (5)	161
Symmetry codes: (i) x-1, y, z; (ii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (v) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ . Cg3 is the centroid of the C9–C14 ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051769/vm2014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051769/vm2014Isup2.hkl

checkCIF report

Comment top

One of the building blocks of cephalosporin antibiotics is 7-amino-deacetoxycephalosporanic acid (7-ADCA). It is currently produced from penicillin G using an elaborate chemical ring-expansion step followed by an enzyme-catalyzed hydrolysis. However, 7-ADCA-like components can also be produced by direct fermentation (Schroen et al. 2000).

In the title molecule (I) shown in Fig. 1, the β-lactam unit (N1/C6–C8) has a twisted conformation with the dihedral angles of 164.7 (4)° and 164.7 (4)° between the planes N1 C6 C7 and C6 C8 C7 and the planes N1 C6 C8 and N1 C8 C7, respectively. The six-membered ring fused to the β-lactam unit, (N1/S1/C1/C2/C4/C6) is puckered with the puckering parameters (Cremer & Pople, 1975): Q_T = 0.618 (3) Å, θ = 54.2 (4) °, ϕ = 340.4 (5) °, respectively.

The crystal stucture is stabilized by intermolecular C—H···S, N—H···O, C—H···O and O—H···O hydrogen bonding interactions between symmetry-related molecules, forming a network in three dimensions (Table 1, Fig. 2). Furthermore, there is a weak C—H···π interaction [C3—H3B···Cg3(-x + 3/2, -y + 1, z + 1/2); H3B···Cg3 = 2.72 Å, C3···Cg3 = 3.640 (5) Å, C3—H3B···Cg3 = 161°, where Cg3 is a centroid of the phenyl ring C9–C14].

Related literature top

For the production of 7-amino-deacetoxycephalosporanic acid-like components by direct fermentation, see: Schroen et al. (2000). For 7-benzenesulfonamido-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid methanol solvate, see: Mariam et al. (2009). For structures with the β-lactam unit, see: Akkurt et al. (2008a,b,c); Baktır et al. (2009); Pınar et al. (2006); Yalçın et al. (2009); Çelik et al. (2009a,b). For puckering parameters, see: Cremer & Pople (1975). Cg3 is the centroid of the C9–C14 ring.

Experimental top

7-ADCA (1 g, 4.7 mmol) was dissolved in distilled water (20 ml) in a round bottom flask (50 ml). Na₂CO₃ (3M) solution was added to maintain the solution at pH 8–9, then benzene sulfonyl chloride (0.82 g, 4.7 mmol) was added dropwise to the solution and stirred at room temperature. As all benzene sulfonyl chloride was consumed, pH becomes stable at 8–9, which confirms the completion of reaction. Then pH was adjusted to 1–2, by using 3 N HCl. The precipitate obtained was filtered, washed with distilled water, dried and recrystalized in ethyl acetate. Light yellow prisms of (I) appeared after two days.

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

	Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The packing and hydrogen bonding of the title compound viewed down a axis. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

7-Benzenesulfonamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene- 2-carboxylic acid monohydrate top

Crystal data top

C₁₄H₁₄N₂O₅S₂·H₂O	F(000) = 776
M_r = 372.43	D_x = 1.426 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1402 reflections
a = 5.9535 (7) Å	θ = 2.8–17.3°
b = 15.8248 (19) Å	µ = 0.34 mm⁻¹
c = 18.411 (2) Å	T = 296 K
V = 1734.6 (3) Å³	Prismatic, light yellow
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	1890 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.064
Graphite monochromator	θ_max = 26.8°, θ_min = 2.6°
ϕ and ω scans	h = −4→7
10847 measured reflections	k = −12→20
3572 independent reflections	l = −15→23

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.055	w = 1/[σ²(F_o²) + (0.0407P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.109	(Δ/σ)_max < 0.001
S = 0.97	Δρ_max = 0.20 e Å⁻³
3572 reflections	Δρ_min = −0.25 e Å⁻³
226 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0083 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1425 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.07 (11)

Crystal data top

C₁₄H₁₄N₂O₅S₂·H₂O	V = 1734.6 (3) Å³
M_r = 372.43	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.9535 (7) Å	µ = 0.34 mm⁻¹
b = 15.8248 (19) Å	T = 296 K
c = 18.411 (2) Å	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	1890 reflections with I > 2σ(I)
10847 measured reflections	R_int = 0.064
3572 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	Δρ_max = 0.20 e Å⁻³
S = 0.97	Δρ_min = −0.25 e Å⁻³
3572 reflections	Absolute structure: Flack (1983), 1425 Friedel pairs
226 parameters	Absolute structure parameter: −0.07 (11)
3 restraints

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

	x	y	z	U_iso*/U_eq
S1	0.8308 (2)	0.30975 (7)	0.07531 (7)	0.0628 (5)
S2	1.06325 (17)	0.48679 (7)	−0.11299 (6)	0.0452 (4)
O1	0.1740 (7)	0.4774 (2)	0.21094 (17)	0.0880 (16)
O2	0.1461 (5)	0.51706 (18)	0.09585 (15)	0.0573 (11)
O3	0.6341 (5)	0.56743 (17)	0.05463 (18)	0.0719 (13)
O4	1.3013 (4)	0.48188 (19)	−0.11039 (15)	0.0595 (11)
O5	0.9420 (5)	0.44363 (17)	−0.16919 (15)	0.0554 (10)
N1	0.5130 (5)	0.42642 (19)	0.06042 (18)	0.0410 (11)
N2	0.9775 (5)	0.44881 (19)	−0.03638 (18)	0.0447 (12)
C1	0.6086 (8)	0.2712 (3)	0.1326 (3)	0.072 (2)
C2	0.4335 (7)	0.3333 (3)	0.1575 (2)	0.0500 (17)
C3	0.2901 (9)	0.2995 (3)	0.2184 (2)	0.077 (2)
C4	0.3988 (6)	0.4074 (3)	0.1247 (2)	0.0427 (16)
C5	0.2262 (7)	0.4725 (3)	0.1418 (3)	0.0507 (17)
C6	0.6407 (7)	0.3665 (2)	0.0176 (2)	0.0500 (17)
C7	0.6267 (6)	0.4950 (3)	0.0341 (2)	0.0480 (16)
C8	0.7372 (7)	0.4416 (3)	−0.0250 (2)	0.0470 (17)
C9	0.9814 (6)	0.5938 (2)	−0.1135 (2)	0.0430 (14)
C10	1.1108 (7)	0.6515 (3)	−0.0765 (2)	0.0587 (17)
C11	1.0450 (10)	0.7349 (3)	−0.0734 (3)	0.074 (2)
C12	0.8513 (10)	0.7598 (3)	−0.1058 (3)	0.069 (2)
C13	0.7206 (8)	0.7021 (3)	−0.1421 (3)	0.0683 (19)
C14	0.7853 (7)	0.6178 (3)	−0.1457 (3)	0.0577 (19)
OW1	0.8355 (9)	0.5874 (3)	0.2110 (3)	0.128 (2)
H1	0.07960	0.51450	0.21690	0.1320*
H1A	0.53260	0.22610	0.10690	0.0860*
H1B	0.67690	0.24650	0.17550	0.0860*
H2	1.07130	0.43340	−0.00340	0.0530*
H3A	0.17150	0.33880	0.22870	0.1160*
H3B	0.38080	0.29200	0.26100	0.1160*
H3C	0.22680	0.24620	0.20430	0.1160*
H6	0.54600	0.32940	−0.01210	0.0600*
H8	0.65710	0.44840	−0.07110	0.0560*
H10	1.24240	0.63430	−0.05370	0.0710*
H11	1.13350	0.77410	−0.04910	0.0890*
H12	0.80690	0.81610	−0.10330	0.0830*
H13	0.58820	0.71950	−0.16430	0.0820*
H14	0.69620	0.57840	−0.16970	0.0690*
HW1	0.706 (6)	0.587 (5)	0.228 (3)	0.1920*
HW2	0.819 (12)	0.614 (4)	0.172 (2)	0.1920*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0590 (8)	0.0401 (6)	0.0892 (10)	0.0106 (6)	0.0078 (8)	0.0044 (6)
S2	0.0366 (6)	0.0512 (7)	0.0479 (7)	0.0031 (5)	0.0001 (6)	0.0012 (6)
O1	0.104 (3)	0.110 (3)	0.050 (2)	0.032 (3)	0.014 (2)	−0.012 (2)
O2	0.0538 (19)	0.0611 (19)	0.057 (2)	0.0140 (18)	0.0046 (17)	−0.0017 (17)
O3	0.062 (2)	0.0368 (17)	0.117 (3)	0.0035 (17)	0.029 (2)	−0.0053 (18)
O4	0.0328 (16)	0.080 (2)	0.0656 (19)	0.0071 (16)	0.0052 (15)	0.0055 (18)
O5	0.0591 (18)	0.0585 (17)	0.0485 (19)	−0.0021 (16)	−0.0076 (17)	−0.0051 (15)
N1	0.0398 (19)	0.0353 (18)	0.048 (2)	0.0017 (17)	0.0067 (18)	−0.0016 (17)
N2	0.029 (2)	0.054 (2)	0.051 (2)	0.0090 (16)	0.0011 (16)	0.0119 (18)
C1	0.077 (4)	0.048 (3)	0.091 (4)	−0.003 (3)	−0.002 (3)	0.012 (3)
C2	0.043 (3)	0.057 (3)	0.050 (3)	−0.010 (3)	0.000 (2)	0.007 (2)
C3	0.080 (4)	0.086 (4)	0.066 (3)	−0.013 (3)	−0.005 (3)	0.017 (3)
C4	0.038 (2)	0.050 (3)	0.040 (3)	−0.005 (2)	−0.001 (2)	−0.002 (2)
C5	0.040 (3)	0.063 (3)	0.049 (3)	−0.005 (2)	0.004 (2)	−0.012 (3)
C6	0.048 (3)	0.046 (3)	0.056 (3)	−0.010 (2)	0.000 (2)	−0.011 (2)
C7	0.041 (3)	0.039 (2)	0.064 (3)	0.005 (2)	0.003 (2)	0.010 (2)
C8	0.037 (3)	0.054 (3)	0.050 (3)	0.006 (2)	−0.003 (2)	0.004 (2)
C9	0.037 (2)	0.044 (2)	0.048 (3)	−0.005 (2)	0.004 (2)	0.007 (2)
C10	0.052 (3)	0.058 (3)	0.066 (3)	−0.005 (3)	−0.012 (3)	0.001 (3)
C11	0.094 (4)	0.046 (3)	0.083 (4)	−0.015 (3)	−0.020 (4)	−0.004 (3)
C12	0.082 (4)	0.044 (3)	0.081 (4)	0.001 (3)	0.009 (4)	0.000 (3)
C13	0.053 (3)	0.062 (3)	0.090 (4)	0.012 (3)	−0.012 (3)	0.013 (3)
C14	0.047 (3)	0.048 (3)	0.078 (4)	−0.004 (2)	−0.004 (3)	0.002 (2)
OW1	0.152 (4)	0.104 (3)	0.129 (4)	0.035 (3)	0.085 (4)	0.000 (3)

Geometric parameters (Å, º) top

S1—C1	1.799 (5)	C6—C8	1.535 (6)
S1—C6	1.793 (4)	C7—C8	1.527 (6)
S2—O4	1.420 (3)	C9—C14	1.363 (6)
S2—O5	1.435 (3)	C9—C10	1.375 (6)
S2—N2	1.616 (3)	C10—C11	1.378 (7)
S2—C9	1.762 (3)	C11—C12	1.357 (8)
O1—C5	1.313 (6)	C12—C13	1.373 (7)
O2—C5	1.200 (6)	C13—C14	1.390 (7)
O3—C7	1.208 (5)	C1—H1B	0.9700
O1—H1	0.8200	C1—H1A	0.9700
OW1—HW2	0.84 (5)	C3—H3C	0.9600
OW1—HW1	0.83 (4)	C3—H3A	0.9600
N1—C4	1.398 (5)	C3—H3B	0.9600
N1—C7	1.368 (5)	C6—H6	0.9800
N1—C6	1.449 (5)	C8—H8	0.9800
N2—C8	1.450 (5)	C10—H10	0.9300
N2—H2	0.8600	C11—H11	0.9300
C1—C2	1.504 (7)	C12—H12	0.9300
C2—C4	1.335 (6)	C13—H13	0.9300
C2—C3	1.507 (6)	C14—H14	0.9300
C4—C5	1.489 (6)

S1···N2	3.136 (3)	C5···OW1ⁱⁱⁱ	3.216 (7)
S1···C5ⁱ	3.698 (5)	C7···O4ⁱⁱⁱ	3.297 (5)
S1···H2	2.8200	C7···O2ⁱ	3.313 (5)
S1···H6ⁱⁱ	2.8000	C7···O2	3.099 (5)
O1···OW1ⁱⁱⁱ	2.663 (6)	C8···C14	3.577 (7)
O1···C3	2.902 (6)	C8···O4ⁱⁱⁱ	3.100 (5)
OW1···O2ⁱ	3.025 (6)	C11···O3^vii	3.192 (6)
OW1···O3	3.135 (6)	C12···O3^vii	3.346 (6)
OW1···C5ⁱ	3.216 (7)	C14···C8	3.577 (7)
OW1···O5^iv	2.799 (6)	C4···H2ⁱⁱⁱ	3.0900
OW1···O1ⁱ	2.663 (6)	C5···H3A	2.6700
O2···N1	2.693 (4)	C5···H2ⁱⁱⁱ	2.8900
O2···C7ⁱⁱⁱ	3.313 (5)	C9···H3B^vi	3.0500
O2···C7	3.099 (5)	C12···H3B^vi	3.0400
O2···OW1ⁱⁱⁱ	3.025 (6)	C13···H3B^vi	2.9700
O2···O3	3.107 (4)	C14···H3B^vi	2.9900
O2···N2ⁱⁱⁱ	2.846 (4)	H1···HW2ⁱⁱⁱ	2.3600
O3···O2	3.107 (4)	H1···OW1ⁱⁱⁱ	1.8600
O3···OW1	3.135 (6)	H1···HW1ⁱⁱⁱ	2.5100
O3···C5	3.276 (6)	HW1···O5^iv	2.14 (5)
O3···C12^v	3.346 (6)	HW1···H1ⁱ	2.5100
O3···N2	3.242 (4)	H1A···H3C	2.5800
O3···C11^v	3.192 (6)	H1B···H3B	2.4700
O4···C7ⁱ	3.297 (5)	H2···O2ⁱ	2.3000
O4···C8ⁱ	3.100 (5)	H2···N1ⁱ	2.8800
O5···OW1^vi	2.799 (6)	H2···S1	2.8200
O1···H3A	2.2200	H2···C5ⁱ	2.8900
OW1···H1ⁱ	1.8600	H2···C4ⁱ	3.0900
O2···HW2ⁱⁱⁱ	2.85 (6)	HW2···O3	2.54 (5)
O2···H2ⁱⁱⁱ	2.3000	HW2···O2ⁱ	2.85 (6)
O2···H12^v	2.8100	HW2···H1ⁱ	2.3600
O3···HW2	2.54 (5)	H3A···O1	2.2200
O3···H12^v	2.8300	H3A···C5	2.6700
O3···H11^v	2.5100	H3B···C12^iv	3.0400
O4···H10	2.6500	H3B···C14^iv	2.9900
O4···H8ⁱ	2.3000	H3B···C9^iv	3.0500
O5···HW1^vi	2.14 (5)	H3B···C13^iv	2.9700
O5···H14	2.5900	H3B···H1B	2.4700
O5···H8	2.4800	H3C···H1A	2.5800
N1···O2	2.693 (4)	H6···S1^viii	2.8000
N2···O2ⁱ	2.846 (4)	H8···O5	2.4800
N2···S1	3.136 (3)	H8···O4ⁱⁱⁱ	2.3000
N2···O3	3.242 (4)	H10···O4	2.6500
N1···H2ⁱⁱⁱ	2.8800	H11···O3^vii	2.5100
C3···O1	2.902 (6)	H12···O3^vii	2.8300
C5···O3	3.276 (6)	H12···O2^vii	2.8100
C5···S1ⁱⁱⁱ	3.698 (5)	H14···O5	2.5900

C1—S1—C6	93.1 (2)	S2—C9—C14	120.5 (3)
O4—S2—O5	120.03 (18)	C10—C9—C14	120.7 (4)
O4—S2—N2	105.40 (17)	C9—C10—C11	119.8 (4)
O4—S2—C9	109.19 (18)	C10—C11—C12	120.1 (5)
O5—S2—N2	107.07 (17)	C11—C12—C13	120.2 (5)
O5—S2—C9	108.33 (17)	C12—C13—C14	120.3 (5)
N2—S2—C9	105.95 (17)	C9—C14—C13	118.9 (4)
C5—O1—H1	110.00	S1—C1—H1A	108.00
HW1—OW1—HW2	103 (6)	S1—C1—H1B	108.00
C6—N1—C7	93.8 (3)	C2—C1—H1B	108.00
C4—N1—C6	125.1 (3)	H1A—C1—H1B	107.00
C4—N1—C7	135.4 (3)	C2—C1—H1A	108.00
S2—N2—C8	117.8 (3)	C2—C3—H3B	109.00
C8—N2—H2	121.00	C2—C3—H3C	109.00
S2—N2—H2	121.00	H3A—C3—H3B	109.00
S1—C1—C2	117.8 (3)	H3A—C3—H3C	110.00
C1—C2—C4	122.9 (4)	H3B—C3—H3C	109.00
C3—C2—C4	124.1 (4)	C2—C3—H3A	109.00
C1—C2—C3	112.8 (4)	S1—C6—H6	113.00
N1—C4—C2	119.8 (4)	C8—C6—H6	113.00
N1—C4—C5	111.5 (4)	N1—C6—H6	113.00
C2—C4—C5	128.2 (4)	C6—C8—H8	110.00
O1—C5—C4	114.2 (4)	C7—C8—H8	110.00
O2—C5—C4	122.1 (5)	N2—C8—H8	110.00
O1—C5—O2	123.7 (4)	C11—C10—H10	120.00
S1—C6—N1	109.7 (3)	C9—C10—H10	120.00
S1—C6—C8	117.0 (3)	C10—C11—H11	120.00
N1—C6—C8	88.2 (3)	C12—C11—H11	120.00
N1—C7—C8	91.5 (3)	C13—C12—H12	120.00
O3—C7—N1	131.3 (4)	C11—C12—H12	120.00
O3—C7—C8	137.1 (4)	C12—C13—H13	120.00
N2—C8—C7	119.0 (3)	C14—C13—H13	120.00
C6—C8—C7	84.4 (3)	C9—C14—H14	121.00
N2—C8—C6	120.3 (4)	C13—C14—H14	121.00
S2—C9—C10	118.7 (3)

C6—S1—C1—C2	−46.4 (4)	S1—C1—C2—C3	−166.4 (3)
C1—S1—C6—N1	57.8 (3)	S1—C1—C2—C4	18.8 (6)
C1—S1—C6—C8	156.1 (3)	C1—C2—C4—N1	6.2 (6)
O4—S2—N2—C8	−176.8 (3)	C1—C2—C4—C5	177.2 (4)
O5—S2—N2—C8	−47.9 (3)	C3—C2—C4—N1	−168.1 (4)
C9—S2—N2—C8	67.6 (3)	C3—C2—C4—C5	3.0 (7)
O4—S2—C9—C10	−32.7 (4)	N1—C4—C5—O1	−155.7 (4)
O4—S2—C9—C14	151.9 (4)	N1—C4—C5—O2	23.2 (6)
O5—S2—C9—C10	−165.0 (3)	C2—C4—C5—O1	32.6 (6)
O5—S2—C9—C14	19.5 (4)	C2—C4—C5—O2	−148.5 (5)
N2—S2—C9—C10	80.4 (3)	S1—C6—C8—N2	19.3 (5)
N2—S2—C9—C14	−95.1 (4)	S1—C6—C8—C7	−101.1 (3)
C6—N1—C4—C2	11.5 (6)	N1—C6—C8—N2	130.5 (4)
C6—N1—C4—C5	−161.0 (4)	N1—C6—C8—C7	10.1 (3)
C7—N1—C4—C2	−134.5 (5)	O3—C7—C8—N2	45.1 (7)
C7—N1—C4—C5	53.1 (6)	O3—C7—C8—C6	166.7 (5)
C4—N1—C6—S1	−49.9 (4)	N1—C7—C8—N2	−132.3 (4)
C4—N1—C6—C8	−168.0 (3)	N1—C7—C8—C6	−10.7 (3)
C7—N1—C6—S1	106.9 (3)	S2—C9—C10—C11	−177.2 (4)
C7—N1—C6—C8	−11.2 (3)	C14—C9—C10—C11	−1.7 (6)
C4—N1—C7—O3	−13.7 (7)	S2—C9—C14—C13	177.0 (4)
C4—N1—C7—C8	164.0 (4)	C10—C9—C14—C13	1.6 (7)
C6—N1—C7—O3	−166.4 (4)	C9—C10—C11—C12	1.0 (7)
C6—N1—C7—C8	11.3 (3)	C10—C11—C12—C13	−0.3 (8)
S2—N2—C8—C6	143.8 (3)	C11—C12—C13—C14	0.2 (8)
S2—N2—C8—C7	−114.9 (3)	C12—C13—C14—C9	−0.8 (8)

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, −z; (iii) x−1, y, z; (iv) −x+3/2, −y+1, z+1/2; (v) x−1/2, −y+3/2, −z; (vi) −x+3/2, −y+1, z−1/2; (vii) x+1/2, −y+3/2, −z; (viii) x−1/2, −y+1/2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···OW1ⁱⁱⁱ	0.82	1.86	2.663 (6)	166
OW1—HW1···O5^iv	0.83 (4)	2.14 (5)	2.799 (6)	136 (5)
N2—H2···S1	0.86	2.82	3.136 (3)	103
N2—H2···O2ⁱ	0.86	2.30	2.846 (4)	122
OW1—HW2···O3	0.84 (5)	2.54 (5)	3.135 (6)	129 (5)
C3—H3A···O1	0.96	2.22	2.902 (6)	127
C6—H6···S1^viii	0.98	2.80	3.756 (4)	165
C8—H8···O4ⁱⁱⁱ	0.98	2.30	3.100 (5)	138
C8—H8···O5	0.98	2.48	2.922 (5)	107
C11—H11···O3^vii	0.93	2.51	3.192 (6)	130
C14—H14···O5	0.93	2.59	2.942 (5)	103
C3—H3B···Cg3^iv	0.96	2.72	3.640 (5)	161

Symmetry codes: (i) x+1, y, z; (iii) x−1, y, z; (iv) −x+3/2, −y+1, z+1/2; (vii) x+1/2, −y+3/2, −z; (viii) x−1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₅S₂·H₂O
M_r	372.43
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.9535 (7), 15.8248 (19), 18.411 (2)
V (Å³)	1734.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10847, 3572, 1890
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.109, 0.97
No. of reflections	3572
No. of parameters	226
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25
Absolute structure	Flack (1983), 1425 Friedel pairs
Absolute structure parameter	−0.07 (11)

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···A	D—H	H···A	D···A	D—H···A
O1—H1···OW1ⁱ	0.8200	1.8600	2.663 (6)	166.00
OW1—HW1···O5ⁱⁱ	0.83 (4)	2.14 (5)	2.799 (6)	136 (5)
N2—H2···S1	0.8600	2.8200	3.136 (3)	103.00
N2—H2···O2ⁱⁱⁱ	0.8600	2.3000	2.846 (4)	122.00
OW1—HW2···O3	0.84 (5)	2.54 (5)	3.135 (6)	129 (5)
C3—H3A···O1	0.9600	2.2200	2.902 (6)	127.00
C6—H6···S1^iv	0.9800	2.8000	3.756 (4)	165.00
C8—H8···O4ⁱ	0.9800	2.3000	3.100 (5)	138.00
C8—H8···O5	0.9800	2.4800	2.922 (5)	107.00
C11—H11···O3^v	0.9300	2.5100	3.192 (6)	130.00
C14—H14···O5	0.9300	2.5900	2.942 (5)	103.00
C3—H3B···Cg3ⁱⁱ	0.96	2.72	3.640 (5)	161

Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, −y+1, z+1/2; (iii) x+1, y, z; (iv) x−1/2, −y+1/2, −z; (v) x+1/2, −y+3/2, −z.

Footnotes

‡Additional correspondence author, e-mail: iukhan@gcu.edu.pk.

References

Akkurt, M., Jarrahpour, A., Ebrahimi, E., Gençaslan, M. & Büyükgüngör, O. (2008a). Acta Cryst. E64, o2466–o2467. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Akkurt, M., Karaca, S., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2008b). Acta Cryst. E64, o902–o903. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Akkurt, M., Karaca, S., Jarrahpour, A. A., Zarei, M. & Büyükgüngör, O. (2008c). Acta Cryst. E64, o924. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Baktır, Z., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009). Acta Cryst. E65, o1623–o1624. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Çelik, Í., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009a). Acta Cryst. E65, o2522–o2523. Web of Science CSD CrossRef IUCr Journals Google Scholar
Çelik, Í., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009b). Acta Cryst. E65, o501–o502. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Mariam, I., Akkurt, M., Sharif, S., Haider, S. K. & Khan, I. U. (2009). Acta Cryst. E65, o1737. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pınar, S., Akkurt, M., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o804–o806. CSD CrossRef IUCr Journals Google Scholar
Schroen, C. G. P. H., VandeWiel, S., Kroon, P. J., DeVroom, E., Janssen, A. E. M. & Tramper, J. (2000). Biotechnol. Bioeng. 70, 654–661. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yalçın, Ş. P., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009). Acta Cryst. E65, o626–o627. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 1| January 2010| Pages o73-o74

doi:10.1107/S1600536809051769

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

7-Benzenesulfonamido-3-methyl-8-oxo-5-thia-1-azabi­cyclo[4.2.0]octa-2-ene-2-carboxylic acid monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

References

organic compounds

7-Benzenesulfonamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid monohydrate