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

In the title compound, C(14)H(14)N(2)O(5)S(2)·H(2)O, the six-membered ring fused to the β-lactam unit has a twisted conformation. Weak intra-molecular N-H⋯S and C-H⋯O inter-actions occur. Inter-molecular C-H⋯S, N-H⋯O, C-H⋯O and O-H⋯O hydrogen-bonding inter-actions stabilize the crystal structure, forming a three-dimensional network. Weak C-H⋯π inter-actions 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 = 372.43

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.109

S = 0.97

3572 reflections

226 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1425 Friedel pairs

Flack parameter: −0.07 (11)

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H14N2O5S2·H2O	F(000) = 776
Mr = 372.43	Dx = 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

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

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(Fo2) + (0.0407P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109	(Δ/σ)max < 0.001
S = 0.97	Δρmax = 0.20 e Å−3
3572 reflections	Δρmin = −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	Flack parameter: −0.07 (11)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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···O3vii	3.192 (6)
OW1···O3	3.135 (6)	C12···O3vii	3.346 (6)
OW1···C5i	3.216 (7)	C14···C8	3.577 (7)
OW1···O5iv	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···H3Bvi	3.0500
O2···C7	3.099 (5)	C12···H3Bvi	3.0400
O2···OW1iii	3.025 (6)	C13···H3Bvi	2.9700
O2···O3	3.107 (4)	C14···H3Bvi	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···O5iv	2.14 (5)
O3···C12v	3.346 (6)	HW1···H1i	2.5100
O3···N2	3.242 (4)	H1A···H3C	2.5800
O3···C11v	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···OW1vi	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···H12v	2.8100	HW2···H1i	2.3600
O3···HW2	2.54 (5)	H3A···O1	2.2200
O3···H12v	2.8300	H3A···C5	2.6700
O3···H11v	2.5100	H3B···C12iv	3.0400
O4···H10	2.6500	H3B···C14iv	2.9900
O4···H8i	2.3000	H3B···C9iv	3.0500
O5···HW1vi	2.14 (5)	H3B···C13iv	2.9700
O5···H14	2.5900	H3B···H1B	2.4700
O5···H8	2.4800	H3C···H1A	2.5800
N1···O2	2.693 (4)	H6···S1viii	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···O3vii	2.5100
C3···O1	2.902 (6)	H12···O3vii	2.8300
C5···O3	3.276 (6)	H12···O2vii	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)

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···O5iv	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···S1viii	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···O3vii	0.93	2.51	3.192 (6)	130
C14—H14···O5	0.93	2.59	2.942 (5)	103
C3—H3B···Cg3iv	0.96	2.72	3.640 (5)	161

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⋯S1iv	0.98	2.80	3.756 (4)	165
C8—H8⋯O4i	0.98	2.30	3.100 (5)	138
C11—H11⋯O3v	0.93	2.51	3.192 (6)	130
C3—H3B⋯Cg3ii	0.96	2.72	3.640 (5)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg3 is the centroid of the C9–C14 ring.