Methyl 4-hy­droxy-2-meth­oxy­carbonyl­methyl-1,1-dioxo-1,2-dihydro-1λ6,2-benzothia­zine-3-carboxyl­ate

Arshad, M.N.; Khan, I.U.; Zia-ur-Rehman, M.; Ahmad, S.A.; Rafique, H.M.

doi:10.1107/S1600536811034921

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2527

doi:10.1107/S1600536811034921

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Methyl 4-hydroxy-2-methoxycarbonylmethyl-1,1-dioxo-1,2-dihydro-1λ⁶,2-benzothiazine-3-carboxylate †

Muhammad Nadeem Arshad,^a ^*‡ Islam Ullah Khan,^b Muhammad Zia-ur-Rehman,^c Sheikh Asrar Ahmad ^d and H. M. Rafique ^a

^aX-ray Diffraction and Crystallography Laboratory, Department of Physics, School of Physical Sciences, University of the Punjab, Quaid-e-Azam Campus, Lahore 54590, Pakistan, ^bMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, ^cApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, and ^dDepartment of Chemistry, Division of Science and Technology, University of Education, Lahore, Pakistan
^*Correspondence e-mail: mnachemist@hotmail.com

(Received 24 August 2011; accepted 25 August 2011; online 31 August 2011)

There are two independent molecules in the asymmetric unit of the title compound, C₁₃H₁₃NO₇S, which have almost identical geometries. The thiazine ring adopts a sofa conformation in both molecules and the molecular conformations are stabilized by intramolecular O—H⋯O hydrogen bonds. Intermolecular C—H⋯O hydrogen bonds stabilize the crystal packing.

Related literature

For related structures, see; Arshad et al. (2009 , 2010 ). For the synthesis, see; Arshad et al. (2011 ).

Experimental

Crystal data

C₁₃H₁₃NO₇S
M_r = 327.30
Triclinic, $[P \overline 1]$
a = 8.9128 (14) Å
b = 12.414 (2) Å
c = 13.443 (2) Å
α = 79.784 (2)°
β = 72.981 (3)°
γ = 88.503 (3)°
V = 1399.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.48 × 0.36 × 0.33 mm

Data collection

Siemens SMART diffractometer equipped with a Bruker APEXII detector
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.882, T_max = 0.917
17331 measured reflections
6923 independent reflections
6322 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.06
6923 reflections
407 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4	0.79 (3)	1.87 (3)	2.5754 (18)	149 (3)
O8—H8O⋯O11	0.98 (3)	1.68 (3)	2.5623 (17)	148 (3)
C13—H13A⋯O10ⁱ	0.98	2.44	3.202 (2)	134
C2—H2⋯O11ⁱⁱ	0.95	2.59	3.339 (2)	136
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and X-SEED (Barbour, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811034921/bt5629sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034921/bt5629Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034921/bt5629Isup3.cml

checkCIF report

Comment top

The crystal structure of title compound is being reported in continuation of our structural studies of various benzothiazines (Arshad et al., 2009, 2010).

The title compound crystallizes with two independent molecules in the asymmetric unit (Fig. 1). In molecule A, the two fused rings are oriented at dihedral angle of 14.18 (7)° while in B this dihedral angle amounts to 18.40 (6)°. The root mean square deviation values for thiazine ring in both molecules are 0.1991Å and 0.2119Å respectively. The alkylated groups attached to the nitrogen atom in molecule A and B are inclined at almost perpendicular position with respect to the thiazine rings and given values are 85.81 (5)° and 88.12 (5)°. Both of the molecules are involved in intra and intermolecular hydrogen bondings. The intramolecular hydrogen bonding of O—H···O type forms six membered ring motif in each molecule. Other inter molecular C—H···O and O—H···O type hydrogen bonding interactions produce three dimensional network (Fig. 2 and Tab. 1).

Related literature top

For related structures, see; Arshad et al. (2009, 2010). For the synthesis, see; Arshad et al. (2011).

Experimental top

The synthesis of title compound is already reported (Arshad et al., 2011). The compound was recrystallized under slow evaporation technique in ethylacetate.

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and X-SEED (Barbour, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The ORTEP diagram of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Unit cell packing of the title compound showing hydrogen bonding interaction as dashed lines.

Methyl 4-hydroxy-2-methoxycarbonylmethyl-1,1-dioxo-1,2-dihydro- 1λ⁶,2-benzothiazine-3-carboxylate top

Crystal data top

C₁₃H₁₃NO₇S	Z = 4
M_r = 327.30	F(000) = 680
Triclinic, P1	D_x = 1.554 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9128 (14) Å	Cell parameters from 9730 reflections
b = 12.414 (2) Å	θ = 2.4–28.9°
c = 13.443 (2) Å	µ = 0.27 mm⁻¹
α = 79.784 (2)°	T = 100 K
β = 72.981 (3)°	Blocks, colorless
γ = 88.503 (3)°	0.48 × 0.36 × 0.33 mm
V = 1399.2 (4) Å³

Data collection top

Siemens SMART diffractometer equipped with a Bruker APEXII detector	6923 independent reflections
Radiation source: fine-focus sealed tube	6322 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 28.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.882, T_max = 0.917	k = −16→16
17331 measured reflections	l = −18→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0516P)² + 0.9585P] where P = (F_o² + 2F_c²)/3
6923 reflections	(Δ/σ)_max = 0.001
407 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₃H₁₃NO₇S	γ = 88.503 (3)°
M_r = 327.30	V = 1399.2 (4) Å³
Triclinic, P1	Z = 4
a = 8.9128 (14) Å	Mo Kα radiation
b = 12.414 (2) Å	µ = 0.27 mm⁻¹
c = 13.443 (2) Å	T = 100 K
α = 79.784 (2)°	0.48 × 0.36 × 0.33 mm
β = 72.981 (3)°

Data collection top

Siemens SMART diffractometer equipped with a Bruker APEXII detector	6923 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	6322 reflections with I > 2σ(I)
T_min = 0.882, T_max = 0.917	R_int = 0.018
17331 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.48 e Å⁻³
6923 reflections	Δρ_min = −0.42 e Å⁻³
407 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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 > 2sigma(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	0.16821 (4)	0.59653 (3)	0.19082 (3)	0.01849 (9)
S2	0.52552 (5)	0.92829 (3)	0.77528 (3)	0.02196 (10)
O8	0.48743 (15)	0.72159 (10)	0.56519 (9)	0.0263 (3)
O1	0.30206 (15)	0.68027 (10)	0.44663 (9)	0.0240 (2)
O12	0.38864 (14)	0.59665 (9)	0.88368 (9)	0.0225 (2)
O4	0.56249 (14)	0.75774 (10)	0.31183 (9)	0.0267 (3)
O7	0.12303 (14)	0.95735 (10)	0.08091 (9)	0.0269 (3)
O11	0.39383 (14)	0.56505 (10)	0.72314 (9)	0.0259 (2)
O14	0.89610 (14)	0.70395 (10)	0.86890 (10)	0.0276 (3)
O3	0.25344 (14)	0.49769 (9)	0.20325 (9)	0.0245 (2)
N1	0.29039 (15)	0.70033 (10)	0.17185 (10)	0.0181 (2)
O13	0.86686 (14)	0.77263 (11)	0.70832 (10)	0.0286 (3)
O2	0.09291 (14)	0.61619 (10)	0.10870 (9)	0.0236 (2)
O5	0.59329 (13)	0.76066 (10)	0.13910 (9)	0.0229 (2)
N2	0.53834 (15)	0.79462 (11)	0.80675 (10)	0.0179 (2)
O9	0.59840 (17)	0.97841 (11)	0.83798 (10)	0.0343 (3)
O6	0.06605 (15)	0.85459 (10)	0.24309 (9)	0.0275 (3)
O10	0.36468 (15)	0.94991 (11)	0.78104 (11)	0.0342 (3)
C19	0.61858 (19)	0.87842 (13)	0.58043 (12)	0.0211 (3)
C11	0.27512 (18)	0.80160 (13)	0.10098 (12)	0.0202 (3)
H11A	0.2567	0.7827	0.0369	0.024*
H11B	0.3751	0.8446	0.0785	0.024*
C3	−0.2273 (2)	0.57856 (14)	0.43419 (13)	0.0249 (3)
H3	−0.3349	0.5583	0.4499	0.030*
C14	0.63731 (19)	0.95418 (13)	0.64225 (12)	0.0203 (3)
C9	0.50907 (19)	0.74369 (12)	0.24092 (12)	0.0201 (3)
C8	0.34682 (18)	0.70707 (12)	0.26034 (12)	0.0189 (3)
C20	0.53123 (18)	0.77482 (13)	0.63114 (12)	0.0200 (3)
C6	0.08927 (18)	0.64003 (12)	0.38905 (12)	0.0188 (3)
C1	0.03184 (18)	0.60509 (12)	0.31319 (12)	0.0187 (3)
C2	−0.12533 (19)	0.57587 (13)	0.33394 (13)	0.0215 (3)
H2	−0.1625	0.5545	0.2807	0.026*
C15	0.7366 (2)	1.04599 (13)	0.60003 (14)	0.0269 (3)
H15	0.7499	1.0952	0.6436	0.032*
C5	−0.01566 (19)	0.64217 (12)	0.48944 (12)	0.0216 (3)
H5	0.0204	0.6651	0.5424	0.026*
C22	0.42446 (18)	0.62469 (13)	0.77922 (12)	0.0204 (3)
C24	0.64439 (19)	0.75062 (14)	0.86710 (12)	0.0229 (3)
H24A	0.6064	0.6760	0.9049	0.027*
H24B	0.6399	0.7964	0.9211	0.027*
C21	0.50090 (17)	0.73286 (12)	0.73654 (12)	0.0184 (3)
C18	0.6976 (2)	0.89909 (15)	0.47193 (13)	0.0302 (4)
H18	0.6846	0.8501	0.4280	0.036*
C12	0.14236 (18)	0.87217 (13)	0.15144 (12)	0.0207 (3)
C25	0.81345 (18)	0.74493 (13)	0.80252 (13)	0.0209 (3)
C4	−0.1721 (2)	0.61080 (13)	0.51154 (13)	0.0246 (3)
H4	−0.2422	0.6113	0.5800	0.029*
C23	0.3242 (2)	0.48585 (14)	0.92729 (14)	0.0303 (4)
H23A	0.2267	0.4773	0.9093	0.045*
H23B	0.3021	0.4727	1.0043	0.045*
H23C	0.4002	0.4330	0.8976	0.045*
C10	0.7541 (2)	0.79979 (16)	0.11653 (14)	0.0290 (4)
H10A	0.7569	0.8799	0.1072	0.043*
H10B	0.8190	0.7768	0.0517	0.043*
H10C	0.7949	0.7690	0.1755	0.043*
C7	0.25286 (19)	0.67701 (12)	0.36224 (12)	0.0195 (3)
C17	0.7950 (3)	0.99176 (17)	0.42903 (14)	0.0366 (4)
H17	0.8479	1.0059	0.3554	0.044*
C13	0.0082 (2)	1.03446 (15)	0.12689 (15)	0.0309 (4)
H13A	−0.0919	0.9955	0.1652	0.046*
H13B	−0.0070	1.0915	0.0705	0.046*
H13C	0.0464	1.0681	0.1759	0.046*
C16	0.8164 (3)	1.06409 (15)	0.49221 (15)	0.0348 (4)
H16	0.8855	1.1260	0.4618	0.042*
C26	1.0610 (2)	0.6897 (2)	0.8203 (2)	0.0437 (5)
H26A	1.0733	0.6389	0.7705	0.066*
H26B	1.1107	0.6600	0.8750	0.066*
H26C	1.1108	0.7606	0.7823	0.066*
H1O	0.389 (4)	0.703 (3)	0.425 (2)	0.066*
H8O	0.437 (4)	0.653 (3)	0.608 (2)	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01975 (18)	0.01908 (18)	0.01976 (18)	0.00083 (13)	−0.00782 (14)	−0.00819 (13)
S2	0.0236 (2)	0.02065 (19)	0.02086 (19)	0.00131 (14)	−0.00283 (14)	−0.00805 (14)
O8	0.0324 (6)	0.0306 (6)	0.0196 (5)	−0.0077 (5)	−0.0116 (5)	−0.0059 (5)
O1	0.0298 (6)	0.0259 (6)	0.0195 (5)	−0.0054 (5)	−0.0127 (5)	−0.0018 (4)
O12	0.0272 (6)	0.0190 (5)	0.0187 (5)	−0.0014 (4)	−0.0031 (4)	−0.0024 (4)
O4	0.0269 (6)	0.0318 (6)	0.0258 (6)	−0.0035 (5)	−0.0129 (5)	−0.0069 (5)
O7	0.0287 (6)	0.0288 (6)	0.0216 (5)	0.0065 (5)	−0.0076 (5)	−0.0012 (5)
O11	0.0279 (6)	0.0255 (6)	0.0253 (6)	−0.0050 (5)	−0.0079 (5)	−0.0062 (5)
O14	0.0231 (6)	0.0296 (6)	0.0337 (6)	0.0044 (5)	−0.0146 (5)	−0.0047 (5)
O3	0.0268 (6)	0.0202 (5)	0.0302 (6)	0.0040 (4)	−0.0102 (5)	−0.0111 (5)
N1	0.0196 (6)	0.0197 (6)	0.0178 (6)	−0.0005 (5)	−0.0083 (5)	−0.0055 (5)
O13	0.0232 (6)	0.0343 (7)	0.0254 (6)	0.0027 (5)	−0.0037 (5)	−0.0036 (5)
O2	0.0236 (6)	0.0301 (6)	0.0216 (5)	−0.0004 (4)	−0.0102 (4)	−0.0097 (5)
O5	0.0193 (5)	0.0272 (6)	0.0239 (5)	−0.0013 (4)	−0.0064 (4)	−0.0088 (4)
N2	0.0194 (6)	0.0204 (6)	0.0160 (6)	0.0000 (5)	−0.0075 (5)	−0.0048 (5)
O9	0.0453 (8)	0.0330 (7)	0.0241 (6)	−0.0119 (6)	−0.0030 (5)	−0.0142 (5)
O6	0.0313 (6)	0.0231 (6)	0.0235 (6)	0.0025 (5)	−0.0023 (5)	−0.0025 (4)
O10	0.0265 (6)	0.0325 (7)	0.0385 (7)	0.0104 (5)	−0.0024 (5)	−0.0063 (6)
C19	0.0250 (8)	0.0216 (7)	0.0185 (7)	−0.0011 (6)	−0.0098 (6)	−0.0021 (6)
C11	0.0222 (7)	0.0225 (7)	0.0167 (7)	0.0009 (6)	−0.0068 (6)	−0.0039 (5)
C3	0.0215 (8)	0.0227 (8)	0.0288 (8)	0.0004 (6)	−0.0061 (6)	−0.0019 (6)
C14	0.0233 (7)	0.0194 (7)	0.0182 (7)	0.0026 (6)	−0.0065 (6)	−0.0031 (5)
C9	0.0230 (7)	0.0169 (7)	0.0227 (7)	0.0013 (5)	−0.0091 (6)	−0.0054 (5)
C8	0.0222 (7)	0.0186 (7)	0.0196 (7)	0.0008 (5)	−0.0099 (6)	−0.0064 (5)
C20	0.0200 (7)	0.0233 (7)	0.0194 (7)	−0.0008 (6)	−0.0081 (6)	−0.0063 (6)
C6	0.0236 (7)	0.0143 (6)	0.0195 (7)	0.0002 (5)	−0.0079 (6)	−0.0028 (5)
C1	0.0226 (7)	0.0155 (6)	0.0189 (7)	0.0012 (5)	−0.0068 (6)	−0.0044 (5)
C2	0.0228 (7)	0.0187 (7)	0.0251 (7)	0.0000 (6)	−0.0097 (6)	−0.0043 (6)
C15	0.0349 (9)	0.0193 (8)	0.0265 (8)	−0.0023 (6)	−0.0085 (7)	−0.0045 (6)
C5	0.0293 (8)	0.0178 (7)	0.0183 (7)	0.0008 (6)	−0.0080 (6)	−0.0028 (5)
C22	0.0167 (7)	0.0230 (7)	0.0216 (7)	0.0013 (5)	−0.0053 (6)	−0.0050 (6)
C24	0.0210 (7)	0.0327 (8)	0.0167 (7)	0.0006 (6)	−0.0090 (6)	−0.0031 (6)
C21	0.0190 (7)	0.0205 (7)	0.0176 (7)	−0.0013 (5)	−0.0068 (5)	−0.0056 (5)
C18	0.0431 (10)	0.0297 (9)	0.0182 (7)	−0.0068 (7)	−0.0091 (7)	−0.0037 (6)
C12	0.0211 (7)	0.0199 (7)	0.0235 (7)	−0.0006 (6)	−0.0102 (6)	−0.0041 (6)
C25	0.0210 (7)	0.0185 (7)	0.0249 (7)	0.0009 (5)	−0.0090 (6)	−0.0045 (6)
C4	0.0269 (8)	0.0220 (8)	0.0219 (7)	0.0033 (6)	−0.0038 (6)	−0.0022 (6)
C23	0.0421 (10)	0.0170 (8)	0.0257 (8)	−0.0006 (7)	−0.0024 (7)	−0.0003 (6)
C10	0.0202 (8)	0.0378 (10)	0.0303 (9)	−0.0047 (7)	−0.0060 (6)	−0.0111 (7)
C7	0.0259 (8)	0.0154 (7)	0.0205 (7)	−0.0001 (5)	−0.0110 (6)	−0.0041 (5)
C17	0.0505 (12)	0.0348 (10)	0.0198 (8)	−0.0098 (8)	−0.0043 (8)	−0.0015 (7)
C13	0.0314 (9)	0.0281 (9)	0.0316 (9)	0.0054 (7)	−0.0085 (7)	−0.0035 (7)
C16	0.0465 (11)	0.0255 (9)	0.0272 (9)	−0.0110 (8)	−0.0048 (8)	0.0004 (7)
C26	0.0275 (10)	0.0493 (12)	0.0578 (13)	0.0141 (9)	−0.0168 (9)	−0.0134 (10)

Geometric parameters (Å, º) top

S1—O2	1.4347 (12)	C14—C15	1.391 (2)
S1—O3	1.4365 (12)	C9—O4	1.2226 (19)
S1—N1	1.6449 (13)	C9—C8	1.462 (2)
S1—C1	1.7548 (16)	C8—C7	1.371 (2)
S2—O9	1.4308 (13)	C20—O8	1.3413 (18)
S2—O10	1.4337 (14)	C20—C21	1.369 (2)
S2—N2	1.6477 (14)	C6—C1	1.401 (2)
S2—C14	1.7504 (16)	C6—C5	1.403 (2)
O8—C20	1.3413 (18)	C6—C7	1.461 (2)
O8—H8O	0.98 (3)	C1—C2	1.391 (2)
O1—C7	1.3377 (18)	C2—H2	0.9500
O1—H1O	0.79 (3)	C15—C16	1.395 (2)
O12—C22	1.3285 (19)	C15—H15	0.9500
O12—C23	1.457 (2)	C5—C4	1.389 (2)
O4—C9	1.2226 (19)	C5—H5	0.9500
O7—C12	1.3330 (19)	C22—C21	1.464 (2)
O7—C13	1.461 (2)	C24—C25	1.510 (2)
O11—C22	1.2329 (19)	C24—H24A	0.9900
O14—C25	1.3423 (19)	C24—H24B	0.9900
O14—C26	1.443 (2)	C18—C17	1.391 (3)
N1—C8	1.4362 (18)	C18—H18	0.9500
N1—C11	1.4658 (19)	C4—H4	0.9500
O13—C25	1.204 (2)	C23—H23A	0.9800
O5—C9	1.3364 (19)	C23—H23B	0.9800
O5—C10	1.4535 (19)	C23—H23C	0.9800
N2—C21	1.4298 (18)	C10—H10A	0.9800
N2—C24	1.4543 (19)	C10—H10B	0.9800
O6—C12	1.204 (2)	C10—H10C	0.9800
C19—C18	1.402 (2)	C17—C16	1.392 (3)
C19—C14	1.403 (2)	C17—H17	0.9500
C19—C20	1.468 (2)	C13—H13A	0.9800
C11—C12	1.521 (2)	C13—H13B	0.9800
C11—H11A	0.9900	C13—H13C	0.9800
C11—H11B	0.9900	C16—H16	0.9500
C3—C4	1.393 (2)	C26—H26A	0.9800
C3—C2	1.393 (2)	C26—H26B	0.9800
C3—H3	0.9500	C26—H26C	0.9800

O2—S1—O3	118.97 (7)	C14—C15—H15	120.8
O2—S1—N1	107.65 (7)	C16—C15—H15	120.8
O3—S1—N1	107.63 (7)	C4—C5—C6	120.16 (15)
O2—S1—C1	110.07 (7)	C4—C5—H5	119.9
O3—S1—C1	108.17 (7)	C6—C5—H5	119.9
N1—S1—C1	103.18 (7)	O11—C22—O12	122.69 (14)
O9—S2—O10	119.43 (9)	O11—C22—C21	122.86 (14)
O9—S2—N2	107.81 (8)	O12—C22—C21	114.45 (13)
O10—S2—N2	107.01 (7)	N2—C24—C25	114.97 (13)
O9—S2—C14	110.62 (8)	N2—C24—H24A	108.5
O10—S2—C14	108.43 (8)	C25—C24—H24A	108.5
N2—S2—C14	102.09 (7)	N2—C24—H24B	108.5
C20—O8—H8O	106.3 (17)	C25—C24—H24B	108.5
C7—O1—H1O	107 (2)	H24A—C24—H24B	107.5
C22—O12—C23	115.47 (13)	C20—C21—N2	120.96 (13)
C12—O7—C13	113.54 (13)	C20—C21—C22	119.85 (13)
C25—O14—C26	115.71 (15)	N2—C21—C22	119.16 (13)
C8—N1—C11	118.88 (12)	C17—C18—C19	119.55 (16)
C8—N1—S1	114.54 (10)	C17—C18—H18	120.2
C11—N1—S1	119.24 (10)	C19—C18—H18	120.2
C9—O5—C10	115.65 (12)	O6—C12—O7	124.32 (15)
C21—N2—C24	119.88 (13)	O6—C12—C11	124.73 (14)
C21—N2—S2	114.97 (10)	O7—C12—C11	110.94 (13)
C24—N2—S2	119.48 (11)	O13—C25—O14	125.30 (15)
C18—C19—C14	118.56 (15)	O13—C25—C24	126.78 (14)
C18—C19—C20	121.16 (14)	O14—C25—C24	107.92 (13)
C14—C19—C20	119.98 (14)	C5—C4—C3	120.59 (15)
N1—C11—C12	113.26 (13)	C5—C4—H4	119.7
N1—C11—H11A	108.9	C3—C4—H4	119.7
C12—C11—H11A	108.9	O12—C23—H23A	109.5
N1—C11—H11B	108.9	O12—C23—H23B	109.5
C12—C11—H11B	108.9	H23A—C23—H23B	109.5
H11A—C11—H11B	107.7	O12—C23—H23C	109.5
C4—C3—C2	120.26 (15)	H23A—C23—H23C	109.5
C4—C3—H3	119.9	H23B—C23—H23C	109.5
C2—C3—H3	119.9	O5—C10—H10A	109.5
C15—C14—C19	122.05 (15)	O5—C10—H10B	109.5
C15—C14—S2	121.66 (12)	H10A—C10—H10B	109.5
C19—C14—S2	116.28 (12)	O5—C10—H10C	109.5
O4—C9—O5	123.11 (14)	H10A—C10—H10C	109.5
O4—C9—O5	123.11 (14)	H10B—C10—H10C	109.5
O4—C9—C8	122.76 (14)	O1—C7—C8	123.00 (14)
O4—C9—C8	122.76 (14)	O1—C7—C6	113.63 (13)
O5—C9—C8	114.13 (13)	C8—C7—C6	123.36 (14)
C7—C8—N1	121.26 (14)	C18—C17—C16	121.10 (17)
C7—C8—C9	119.61 (13)	C18—C17—H17	119.4
N1—C8—C9	119.10 (13)	C16—C17—H17	119.4
O8—C20—C21	121.98 (14)	O7—C13—H13A	109.5
O8—C20—C21	121.98 (14)	O7—C13—H13B	109.5
O8—C20—C19	114.68 (13)	H13A—C13—H13B	109.5
O8—C20—C19	114.68 (13)	O7—C13—H13C	109.5
C21—C20—C19	123.29 (14)	H13A—C13—H13C	109.5
C1—C6—C5	118.23 (14)	H13B—C13—H13C	109.5
C1—C6—C7	120.43 (14)	C17—C16—C15	120.20 (17)
C5—C6—C7	121.30 (14)	C17—C16—H16	119.9
C2—C1—C6	121.94 (14)	C15—C16—H16	119.9
C2—C1—S1	120.99 (12)	O14—C26—H26A	109.5
C6—C1—S1	117.05 (12)	O14—C26—H26B	109.5
C1—C2—C3	118.78 (15)	H26A—C26—H26B	109.5
C1—C2—H2	120.6	O14—C26—H26C	109.5
C3—C2—H2	120.6	H26A—C26—H26C	109.5
C14—C15—C16	118.48 (16)	H26B—C26—H26C	109.5

O2—S1—N1—C8	165.62 (10)	N1—S1—C1—C2	145.82 (13)
O3—S1—N1—C8	−65.00 (12)	O2—S1—C1—C6	−150.26 (12)
C1—S1—N1—C8	49.24 (12)	O3—S1—C1—C6	78.24 (13)
O2—S1—N1—C11	15.84 (13)	N1—S1—C1—C6	−35.61 (13)
O3—S1—N1—C11	145.22 (11)	C6—C1—C2—C3	−1.9 (2)
C1—S1—N1—C11	−100.54 (12)	S1—C1—C2—C3	176.63 (12)
O9—S2—N2—C21	−167.55 (11)	C4—C3—C2—C1	0.5 (2)
O10—S2—N2—C21	62.81 (12)	C19—C14—C15—C16	1.7 (3)
C14—S2—N2—C21	−50.99 (12)	S2—C14—C15—C16	−176.97 (15)
O9—S2—N2—C24	−14.11 (14)	C1—C6—C5—C4	−0.4 (2)
O10—S2—N2—C24	−143.74 (12)	C7—C6—C5—C4	177.35 (14)
C14—S2—N2—C24	102.45 (12)	C23—O12—C22—O11	5.7 (2)
C8—N1—C11—C12	−70.27 (17)	C23—O12—C22—C21	−175.20 (14)
S1—N1—C11—C12	78.20 (15)	C21—N2—C24—C25	69.53 (18)
C18—C19—C14—C15	−2.8 (3)	S2—N2—C24—C25	−82.61 (16)
C20—C19—C14—C15	170.92 (15)	O8—C20—C21—N2	−175.35 (14)
C18—C19—C14—S2	175.91 (13)	O8—C20—C21—N2	−175.35 (14)
C20—C19—C14—S2	−10.3 (2)	C19—C20—C21—N2	7.1 (2)
O9—S2—C14—C15	−25.92 (17)	O8—C20—C21—C22	2.7 (2)
O10—S2—C14—C15	106.82 (15)	O8—C20—C21—C22	2.7 (2)
N2—S2—C14—C15	−140.43 (14)	C19—C20—C21—C22	−174.91 (14)
O9—S2—C14—C19	155.31 (13)	C24—N2—C21—C20	−121.58 (16)
O10—S2—C14—C19	−71.94 (14)	S2—N2—C21—C20	31.75 (19)
N2—S2—C14—C19	40.81 (14)	C24—N2—C21—C22	60.39 (19)
O4—O4—C9—O5	0.00 (13)	S2—N2—C21—C22	−146.28 (12)
O4—O4—C9—C8	0.00 (6)	O11—C22—C21—C20	4.7 (2)
C10—O5—C9—O4	−1.3 (2)	O12—C22—C21—C20	−174.38 (14)
C10—O5—C9—O4	−1.3 (2)	O11—C22—C21—N2	−177.28 (14)
C10—O5—C9—C8	178.51 (14)	O12—C22—C21—N2	3.7 (2)
C11—N1—C8—C7	114.97 (16)	C14—C19—C18—C17	1.7 (3)
S1—N1—C8—C7	−34.92 (18)	C20—C19—C18—C17	−171.98 (18)
C11—N1—C8—C9	−66.85 (18)	C13—O7—C12—O6	5.0 (2)
S1—N1—C8—C9	143.26 (12)	C13—O7—C12—C11	−174.02 (13)
O4—C9—C8—C7	−6.3 (2)	N1—C11—C12—O6	7.2 (2)
O4—C9—C8—C7	−6.3 (2)	N1—C11—C12—O7	−173.69 (12)
O5—C9—C8—C7	173.89 (13)	C26—O14—C25—O13	−2.1 (2)
O4—C9—C8—N1	175.49 (14)	C26—O14—C25—C24	178.36 (15)
O4—C9—C8—N1	175.49 (14)	N2—C24—C25—O13	−0.1 (2)
O5—C9—C8—N1	−4.3 (2)	N2—C24—C25—O14	179.43 (13)
O8—O8—C20—C21	0.00 (15)	C6—C5—C4—C3	−1.0 (2)
O8—O8—C20—C19	0.00 (19)	C2—C3—C4—C5	1.0 (2)
C18—C19—C20—O8	−22.0 (2)	N1—C8—C7—O1	178.77 (13)
C14—C19—C20—O8	164.35 (14)	C9—C8—C7—O1	0.6 (2)
C18—C19—C20—O8	−22.0 (2)	N1—C8—C7—C6	−2.2 (2)
C14—C19—C20—O8	164.35 (14)	C9—C8—C7—C6	179.64 (14)
C18—C19—C20—C21	155.70 (17)	C1—C6—C7—O1	−163.40 (14)
C14—C19—C20—C21	−17.9 (2)	C5—C6—C7—O1	18.9 (2)
C5—C6—C1—C2	1.8 (2)	C1—C6—C7—C8	17.5 (2)
C7—C6—C1—C2	−175.91 (14)	C5—C6—C7—C8	−160.19 (15)
C5—C6—C1—S1	−176.74 (11)	C19—C18—C17—C16	0.5 (3)
C7—C6—C1—S1	5.53 (19)	C18—C17—C16—C15	−1.6 (3)
O2—S1—C1—C2	31.17 (15)	C14—C15—C16—C17	0.5 (3)
O3—S1—C1—C2	−100.33 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.79 (3)	1.87 (3)	2.5754 (18)	149 (3)
O8—H8O···O11	0.98 (3)	1.68 (3)	2.5623 (17)	148 (3)
C13—H13A···O10ⁱ	0.98	2.44	3.202 (2)	134
C2—H2···O11ⁱⁱ	0.95	2.59	3.339 (2)	136

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO₇S
M_r	327.30
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.9128 (14), 12.414 (2), 13.443 (2)
α, β, γ (°)	79.784 (2), 72.981 (3), 88.503 (3)
V (Å³)	1399.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.48 × 0.36 × 0.33

Data collection
Diffractometer	Siemens SMART diffractometer equipped with a Bruker APEXII detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.882, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	17331, 6923, 6322
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.681

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.06
No. of reflections	6923
No. of parameters	407
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.42

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and X-SEED (Barbour, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.79 (3)	1.87 (3)	2.5754 (18)	149 (3)
O8—H8O···O11	0.98 (3)	1.68 (3)	2.5623 (17)	148 (3)
C13—H13A···O10ⁱ	0.98	2.44	3.202 (2)	134.4
C2—H2···O11ⁱⁱ	0.95	2.59	3.339 (2)	136.0

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

Footnotes

†I (MNA) dedicate this article to my first child (a boy), Mr Muhammad Ali Hassan, as he was born on 22nd August 2011, the day I compiled this article.

‡Materials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan.

Acknowledgements

MNA acknowledges the Higher Education Commission of Pakistan for granting a scholarship under its indigenous and IRSIP schemes.

References

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