Methyl 4-hydr­oxy-2H-1,2-benzothia­zine-3-carboxyl­ate 1,1-dioxide

Siddiqui, W.A.; Ahmad, S.; Siddiqui, H.L.; Bukhari, M.H.; Parvez, M.

doi:10.1107/S1600536808028584

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1922

doi:10.1107/S1600536808028584

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Methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Waseeq Ahmad Siddiqui,^a ^* Saeed Ahmad,^b Hamid Latif Siddiqui,^c Mujahid Hussain Bukhari ^c and Masood Parvez ^d

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, University of Science and Technology, Bannu, Pakistan, ^cInstitute of Chemistry, University of the Punjab, Lahore, Pakistan, and ^dDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada, T2N 1N4
^*Correspondence e-mail: waseeq_786@yahoo.com

(Received 20 August 2008; accepted 6 September 2008; online 13 September 2008)

The asymmetric unit of the title compound, C₁₀H₉NO₅S, contains two independent molecules. The heterocyclic thiazine rings in both molecules adopt half-chair conformations, with the S atoms in each molecule displaced by 0.455 (3) and 0.539 (3) Å and the N atoms displaced in the opposite direction by 0.214 (3) and 0.203 (3) Å, from the planes defined by the remaining ring atoms. The crystal structure is stabilized by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds involving both inter- and intramolecular interactions.

Related literature

For related literature, see: Banerjee & Sarkar (2002 ); Cremer & Pople, 1975 ; Hirai et al. (1997 ); Khalil et al. (2000 ); Myung et al. (2002 ); Siddiqui et al. (2006 , 2008 ).

Experimental

Crystal data

C₁₀H₉NO₅S
M_r = 255.24
Triclinic, $[P \overline 1]$
a = 7.777 (2) Å
b = 10.932 (4) Å
c = 12.890 (4) Å
α = 105.569 (16)°
β = 94.588 (15)°
γ = 97.763 (16)°
V = 1038.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 173 (2) K
0.24 × 0.22 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.927, T_max = 0.950
8716 measured reflections
4693 independent reflections
4191 reflections with (I) > 2.0 σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.03
4693 reflections
321 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4	0.81 (2)	1.86 (2)	2.600 (2)	152 (2)
N1—H1N⋯O9	0.81 (2)	2.22 (2)	2.994 (2)	162 (2)
O6—H6O⋯O9	0.81 (2)	1.91 (2)	2.634 (2)	147 (2)
N2—H2N⋯O3ⁱ	0.83 (2)	2.13 (2)	2.966 (2)	175 (2)
C4—H4⋯O8ⁱⁱ	0.95	2.36	3.259 (2)	158
C20—H20A⋯O2ⁱ	0.98	2.51	3.267 (2)	134
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z-1.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: HKL DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S1600536808028584/lh2686sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028584/lh2686Isup2.hkl

checkCIF report

Comment top

The 1,2-benzothiazine-3-carboxamide 1,1-dioxide derivatives belong to oxicams, a new class of non-steroidal anti-inflammatory drugs (NSAIDs). They are important for their analgesic and anti-inflammatory activities (Hirai et al., 1997, Khalil et al., 2000; Myung et al., 2002). Besides great therapeutic potential, these are very motivating polyfunctional heterocyclic molecules by virtue of their dynamic structural features, which include different tautomeric forms and their possible polymorphism (Banerjee et al., 2002). Continuing our investigations in this important field, (Siddiqui et al., 2006, 2008), we now report the crystal structure of the title compound, (I), in this paper.

An asymmetric unit of (I) contains two independent molecules presented in Figures 1 (molecule a) and 2 (molecule b). The heterocyclic thiazine rings in both molecules adopt half-chair conformations, with atoms S1 and N1 in molecule a and atoms S2 and N2 in molecule b displaced by -0.455 (3), 0.214 (3), -0.539 (3) and 0.203 (3) Å, from the planes defined by C1/C6/C7/C8 and C11/C16/C17/C18, respectively; the puckering parameters (Cremer & Pople, 1975) are Q = 0.4365 (12) and 0.4901 (12) Å, θ = 61.8 (2) and 64.1 (2)° and ϕ = 19.6 (2) and 17.5 (2)°, respectively. Similar conformations of the corresponding rings have been reported in some closely related compounds (Siddiqui et al., 2008).

The structure is stabilized by classical as well as non-classical hydrogen bonding (Fig. 3). Details of the hydrogen bonding geometry have been provided in Table 1.

Related literature top

For related literature, see: Banerjee & Sarkar (2002); Cremer & Pople, 1975; Hirai et al. (1997); Khalil et al. (2000); Myung et al. (2002); Siddiqui et al. (2006, 2008).

Experimental top

The synthesis of the title compound as an important intermediate in the synthesis of oxicams has been reported (Siddiqui et al., 2006). Crystals suitable for crystallographic studies were obtained from a solution of MeOH by slow evaporation at 313 K.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of molecule a with displacement ellipsoids plotted at 50% probability level.
	Fig. 2. ORTEP-3 (Farrugia, 1997) drawing of molecule b with displacement ellipsoids plotted at 50% probability level.
	Fig. 3. Part of the crystal structure showing H-bonding interactions (classical in red, non-classical in green and intramolecular in black) indicated by dashed lines, H-atoms not involved in H-bonds have been excluded.

Methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide top

Crystal data top

C₁₀H₉NO₅S	Z = 4
M_r = 255.24	F(000) = 528
Triclinic, P1	D_x = 1.633 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.777 (2) Å	Cell parameters from 8716 reflections
b = 10.932 (4) Å	θ = 3.3–27.5°
c = 12.890 (4) Å	µ = 0.32 mm⁻¹
α = 105.569 (16)°	T = 173 K
β = 94.588 (15)°	Block, colorless
γ = 97.763 (16)°	0.24 × 0.22 × 0.16 mm
V = 1038.2 (6) Å³

Data collection top

Nonius KappaCCD diffractometer	4693 independent reflections
Radiation source: fine-focus sealed tube	4191 reflections with (I) > 2.0 σ(I)
Graphite monochromator	R_int = 0.019
ω and ϕ scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→10
T_min = 0.927, T_max = 0.950	k = −14→13
8716 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.041P)² + 0.6P] where P = (F_o² + 2F_c²)/3
4693 reflections	(Δ/σ)_max = 0.001
321 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₀H₉NO₅S	γ = 97.763 (16)°
M_r = 255.24	V = 1038.2 (6) Å³
Triclinic, P1	Z = 4
a = 7.777 (2) Å	Mo Kα radiation
b = 10.932 (4) Å	µ = 0.32 mm⁻¹
c = 12.890 (4) Å	T = 173 K
α = 105.569 (16)°	0.24 × 0.22 × 0.16 mm
β = 94.588 (15)°

Data collection top

Nonius KappaCCD diffractometer	4693 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	4191 reflections with (I) > 2.0 σ(I)
T_min = 0.927, T_max = 0.950	R_int = 0.019
8716 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.39 e Å⁻³
4693 reflections	Δρ_min = −0.41 e Å⁻³
321 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.30114 (5)	0.07908 (3)	0.24748 (3)	0.01734 (10)
O1	0.23427 (16)	−0.14432 (12)	−0.08819 (9)	0.0293 (3)
H1O	0.263 (3)	−0.213 (2)	−0.0882 (18)	0.035*
O2	0.40121 (15)	0.17533 (10)	0.33806 (9)	0.0245 (2)
O3	0.14058 (14)	0.00794 (10)	0.26334 (9)	0.0218 (2)
O4	0.37308 (17)	−0.31701 (11)	−0.02096 (9)	0.0311 (3)
O5	0.49305 (15)	−0.26084 (10)	0.15392 (9)	0.0243 (2)
N1	0.42676 (17)	−0.02186 (12)	0.19684 (10)	0.0200 (3)
H1N	0.528 (3)	−0.0058 (18)	0.2220 (16)	0.024*
C1	0.25147 (19)	0.14330 (14)	0.13951 (12)	0.0192 (3)
C2	0.2150 (2)	0.26789 (15)	0.16002 (13)	0.0247 (3)
H2	0.2298	0.3231	0.2320	0.030*
C3	0.1567 (2)	0.31014 (17)	0.07309 (15)	0.0297 (4)
H3	0.1312	0.3951	0.0855	0.036*
C4	0.1354 (2)	0.22878 (18)	−0.03175 (14)	0.0303 (4)
H4	0.0919	0.2579	−0.0903	0.036*
C5	0.1764 (2)	0.10609 (17)	−0.05230 (13)	0.0251 (3)
H5	0.1628	0.0520	−0.1247	0.030*
C6	0.23809 (18)	0.06130 (15)	0.03369 (12)	0.0195 (3)
C7	0.28587 (19)	−0.06738 (15)	0.01323 (12)	0.0207 (3)
C8	0.37515 (19)	−0.10618 (14)	0.09083 (12)	0.0194 (3)
C9	0.4123 (2)	−0.23777 (15)	0.06838 (12)	0.0220 (3)
C10	0.5260 (3)	−0.39148 (16)	0.13991 (15)	0.0326 (4)
H10A	0.5654	−0.4022	0.2106	0.039*
H10B	0.6167	−0.4083	0.0917	0.039*
H10C	0.4183	−0.4522	0.1079	0.039*
S2	0.86977 (5)	0.34163 (3)	0.69700 (3)	0.01856 (10)
O6	0.98831 (15)	0.24939 (12)	0.36870 (9)	0.0243 (2)
H6O	0.932 (3)	0.180 (2)	0.3347 (17)	0.029*
O7	0.72248 (14)	0.39245 (11)	0.66203 (9)	0.0253 (2)
O8	0.89790 (15)	0.34412 (11)	0.80904 (9)	0.0252 (2)
O9	0.77047 (14)	0.03249 (11)	0.33635 (9)	0.0261 (2)
O10	0.70377 (16)	−0.02541 (11)	0.48543 (9)	0.0271 (3)
N2	0.86481 (19)	0.19551 (13)	0.62361 (10)	0.0237 (3)
H2N	0.869 (3)	0.138 (2)	0.6548 (16)	0.028*
C11	1.05550 (19)	0.41894 (14)	0.65790 (12)	0.0187 (3)
C12	1.1639 (2)	0.52218 (15)	0.73162 (13)	0.0235 (3)
H12	1.1443	0.5475	0.8056	0.028*
C13	1.3017 (2)	0.58800 (15)	0.69539 (14)	0.0268 (3)
H13	1.3775	0.6586	0.7448	0.032*
C14	1.3285 (2)	0.55026 (16)	0.58671 (14)	0.0263 (3)
H14	1.4209	0.5970	0.5621	0.032*
C15	1.2225 (2)	0.44570 (15)	0.51417 (13)	0.0226 (3)
H15	1.2436	0.4204	0.4404	0.027*
C16	1.08448 (19)	0.37690 (14)	0.54858 (12)	0.0188 (3)
C17	0.97645 (19)	0.26167 (14)	0.47423 (12)	0.0189 (3)
C18	0.8758 (2)	0.17361 (14)	0.51071 (12)	0.0202 (3)
C19	0.77841 (19)	0.05550 (15)	0.43550 (12)	0.0210 (3)
C20	0.6136 (2)	−0.14884 (16)	0.41616 (14)	0.0314 (4)
H20A	0.5696	−0.2026	0.4612	0.038*
H20B	0.6949	−0.1918	0.3703	0.038*
H20C	0.5154	−0.1354	0.3702	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02110 (18)	0.01460 (17)	0.01551 (17)	0.00158 (13)	0.00185 (13)	0.00366 (13)
O1	0.0381 (7)	0.0269 (6)	0.0176 (5)	0.0025 (5)	−0.0021 (5)	0.0001 (5)
O2	0.0315 (6)	0.0189 (5)	0.0189 (5)	0.0002 (4)	−0.0004 (4)	0.0010 (4)
O3	0.0232 (5)	0.0212 (5)	0.0227 (5)	0.0017 (4)	0.0056 (4)	0.0091 (4)
O4	0.0415 (7)	0.0223 (6)	0.0243 (6)	0.0063 (5)	0.0025 (5)	−0.0023 (5)
O5	0.0300 (6)	0.0194 (5)	0.0242 (5)	0.0078 (4)	0.0048 (4)	0.0052 (4)
N1	0.0187 (6)	0.0191 (6)	0.0189 (6)	0.0035 (5)	−0.0025 (5)	0.0009 (5)
C1	0.0182 (7)	0.0201 (7)	0.0203 (7)	0.0006 (5)	0.0029 (5)	0.0087 (6)
C2	0.0268 (8)	0.0227 (8)	0.0274 (8)	0.0053 (6)	0.0072 (6)	0.0100 (6)
C3	0.0292 (8)	0.0280 (8)	0.0400 (9)	0.0088 (7)	0.0099 (7)	0.0196 (7)
C4	0.0251 (8)	0.0404 (10)	0.0338 (9)	0.0062 (7)	0.0037 (7)	0.0243 (8)
C5	0.0214 (7)	0.0342 (9)	0.0213 (7)	0.0020 (6)	0.0018 (6)	0.0119 (7)
C6	0.0153 (6)	0.0233 (7)	0.0200 (7)	−0.0004 (5)	0.0019 (5)	0.0081 (6)
C7	0.0200 (7)	0.0223 (7)	0.0169 (7)	−0.0005 (6)	0.0028 (5)	0.0026 (6)
C8	0.0200 (7)	0.0172 (7)	0.0179 (7)	0.0014 (5)	0.0017 (5)	0.0006 (5)
C9	0.0225 (7)	0.0201 (7)	0.0222 (7)	0.0022 (6)	0.0058 (6)	0.0037 (6)
C10	0.0453 (10)	0.0215 (8)	0.0359 (9)	0.0137 (7)	0.0117 (8)	0.0105 (7)
S2	0.02101 (18)	0.01819 (18)	0.01673 (17)	0.00130 (13)	0.00248 (13)	0.00623 (13)
O6	0.0270 (6)	0.0265 (6)	0.0175 (5)	0.0004 (5)	0.0052 (4)	0.0045 (4)
O7	0.0216 (5)	0.0304 (6)	0.0277 (6)	0.0065 (4)	0.0061 (4)	0.0128 (5)
O8	0.0328 (6)	0.0254 (6)	0.0168 (5)	0.0017 (5)	0.0022 (4)	0.0069 (4)
O9	0.0244 (5)	0.0298 (6)	0.0193 (5)	−0.0009 (5)	0.0018 (4)	0.0019 (4)
O10	0.0362 (6)	0.0198 (5)	0.0211 (5)	−0.0044 (5)	−0.0014 (5)	0.0044 (4)
N2	0.0358 (7)	0.0173 (6)	0.0172 (6)	−0.0004 (5)	0.0012 (5)	0.0065 (5)
C11	0.0184 (7)	0.0171 (7)	0.0224 (7)	0.0042 (5)	0.0023 (5)	0.0080 (6)
C12	0.0247 (7)	0.0204 (7)	0.0236 (7)	0.0028 (6)	0.0036 (6)	0.0032 (6)
C13	0.0240 (8)	0.0193 (7)	0.0326 (8)	−0.0013 (6)	0.0021 (6)	0.0024 (6)
C14	0.0209 (7)	0.0236 (8)	0.0358 (9)	0.0023 (6)	0.0085 (6)	0.0102 (7)
C15	0.0221 (7)	0.0222 (7)	0.0252 (7)	0.0054 (6)	0.0066 (6)	0.0077 (6)
C16	0.0185 (7)	0.0175 (7)	0.0217 (7)	0.0053 (5)	0.0019 (5)	0.0068 (6)
C17	0.0184 (7)	0.0211 (7)	0.0176 (7)	0.0055 (5)	0.0020 (5)	0.0051 (6)
C18	0.0228 (7)	0.0191 (7)	0.0174 (7)	0.0030 (6)	0.0004 (5)	0.0039 (6)
C19	0.0188 (7)	0.0219 (7)	0.0214 (7)	0.0039 (6)	0.0008 (5)	0.0048 (6)
C20	0.0410 (10)	0.0193 (8)	0.0267 (8)	−0.0059 (7)	−0.0052 (7)	0.0026 (6)

Geometric parameters (Å, º) top

S1—O2	1.4318 (12)	S2—O7	1.4310 (12)
S1—O3	1.4386 (11)	S2—O8	1.4356 (12)
S1—N1	1.6139 (14)	S2—N2	1.6170 (15)
S1—C1	1.7581 (15)	S2—C11	1.7521 (15)
O1—C7	1.3462 (18)	O6—C17	1.3426 (18)
O1—H1O	0.81 (2)	O6—H6O	0.81 (2)
O4—C9	1.2273 (19)	O9—C19	1.2292 (19)
O5—C9	1.3246 (19)	O10—C19	1.3267 (19)
O5—C10	1.4513 (19)	O10—C20	1.4516 (19)
N1—C8	1.4192 (19)	N2—C18	1.4216 (19)
N1—H1N	0.81 (2)	N2—H2N	0.83 (2)
C1—C2	1.389 (2)	C11—C12	1.388 (2)
C1—C6	1.404 (2)	C11—C16	1.407 (2)
C2—C3	1.389 (2)	C12—C13	1.392 (2)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.387 (3)	C13—C14	1.391 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.382 (3)	C14—C15	1.382 (2)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.403 (2)	C15—C16	1.397 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.464 (2)	C16—C17	1.466 (2)
C7—C8	1.363 (2)	C17—C18	1.363 (2)
C8—C9	1.463 (2)	C18—C19	1.459 (2)
C10—H10A	0.9800	C20—H20A	0.9800
C10—H10B	0.9800	C20—H20B	0.9800
C10—H10C	0.9800	C20—H20C	0.9800

O2—S1—O3	119.12 (7)	O7—S2—O8	118.19 (7)
O2—S1—N1	107.80 (7)	O7—S2—N2	110.26 (8)
O3—S1—N1	108.47 (7)	O8—S2—N2	108.16 (7)
O2—S1—C1	111.19 (7)	O7—S2—C11	107.46 (7)
O3—S1—C1	106.82 (7)	O8—S2—C11	110.99 (7)
N1—S1—C1	102.09 (7)	N2—S2—C11	100.30 (7)
C7—O1—H1O	105.2 (16)	C17—O6—H6O	107.2 (14)
C9—O5—C10	116.20 (13)	C19—O10—C20	116.26 (13)
C8—N1—S1	118.66 (10)	C18—N2—S2	118.32 (11)
C8—N1—H1N	120.1 (14)	C18—N2—H2N	122.7 (14)
S1—N1—H1N	117.5 (14)	S2—N2—H2N	118.5 (14)
C2—C1—C6	122.02 (14)	C12—C11—C16	121.77 (14)
C2—C1—S1	120.29 (12)	C12—C11—S2	120.58 (12)
C6—C1—S1	117.53 (11)	C16—C11—S2	117.57 (11)
C1—C2—C3	118.62 (15)	C11—C12—C13	118.93 (15)
C1—C2—H2	120.7	C11—C12—H12	120.5
C3—C2—H2	120.7	C13—C12—H12	120.5
C4—C3—C2	120.26 (16)	C14—C13—C12	119.95 (15)
C4—C3—H3	119.9	C14—C13—H13	120.0
C2—C3—H3	119.9	C12—C13—H13	120.0
C5—C4—C3	121.02 (15)	C15—C14—C13	120.86 (15)
C5—C4—H4	119.5	C15—C14—H14	119.6
C3—C4—H4	119.5	C13—C14—H14	119.6
C4—C5—C6	120.04 (15)	C14—C15—C16	120.39 (15)
C4—C5—H5	120.0	C14—C15—H15	119.8
C6—C5—H5	120.0	C16—C15—H15	119.8
C5—C6—C1	117.94 (14)	C15—C16—C11	118.04 (14)
C5—C6—C7	120.79 (14)	C15—C16—C17	121.18 (14)
C1—C6—C7	121.28 (13)	C11—C16—C17	120.75 (13)
O1—C7—C8	122.72 (14)	O6—C17—C18	123.41 (14)
O1—C7—C6	114.65 (13)	O6—C17—C16	114.53 (13)
C8—C7—C6	122.63 (13)	C18—C17—C16	122.04 (13)
C7—C8—N1	120.81 (13)	C17—C18—N2	120.21 (13)
C7—C8—C9	120.74 (14)	C17—C18—C19	121.04 (14)
N1—C8—C9	118.38 (13)	N2—C18—C19	118.75 (13)
O4—C9—O5	124.32 (14)	O9—C19—O10	123.81 (14)
O4—C9—C8	122.83 (14)	O9—C19—C18	123.27 (14)
O5—C9—C8	112.84 (13)	O10—C19—C18	112.90 (13)
O5—C10—H10A	109.5	O10—C20—H20A	109.5
O5—C10—H10B	109.5	O10—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
O5—C10—H10C	109.5	O10—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5

O2—S1—N1—C8	−163.59 (11)	O7—S2—N2—C18	62.59 (13)
O3—S1—N1—C8	66.16 (13)	O8—S2—N2—C18	−166.78 (11)
C1—S1—N1—C8	−46.39 (13)	C11—S2—N2—C18	−50.50 (13)
O2—S1—C1—C2	−36.33 (14)	O7—S2—C11—C12	98.46 (13)
O3—S1—C1—C2	95.16 (13)	O8—S2—C11—C12	−32.17 (15)
N1—S1—C1—C2	−151.06 (12)	N2—S2—C11—C12	−146.32 (13)
O2—S1—C1—C6	148.12 (11)	O7—S2—C11—C16	−78.25 (13)
O3—S1—C1—C6	−80.39 (12)	O8—S2—C11—C16	151.13 (11)
N1—S1—C1—C6	33.39 (13)	N2—S2—C11—C16	36.98 (13)
C6—C1—C2—C3	2.7 (2)	C16—C11—C12—C13	1.9 (2)
S1—C1—C2—C3	−172.61 (12)	S2—C11—C12—C13	−174.65 (12)
C1—C2—C3—C4	0.1 (2)	C11—C12—C13—C14	0.3 (2)
C2—C3—C4—C5	−1.9 (3)	C12—C13—C14—C15	−1.7 (2)
C3—C4—C5—C6	1.0 (2)	C13—C14—C15—C16	0.9 (2)
C4—C5—C6—C1	1.7 (2)	C14—C15—C16—C11	1.2 (2)
C4—C5—C6—C7	−178.64 (14)	C14—C15—C16—C17	−176.71 (14)
C2—C1—C6—C5	−3.6 (2)	C12—C11—C16—C15	−2.7 (2)
S1—C1—C6—C5	171.83 (11)	S2—C11—C16—C15	174.00 (11)
C2—C1—C6—C7	176.74 (14)	C12—C11—C16—C17	175.28 (14)
S1—C1—C6—C7	−7.80 (18)	S2—C11—C16—C17	−8.05 (18)
C5—C6—C7—O1	−12.3 (2)	C15—C16—C17—O6	−17.4 (2)
C1—C6—C7—O1	167.33 (13)	C11—C16—C17—O6	164.76 (13)
C5—C6—C7—C8	167.84 (14)	C15—C16—C17—C18	161.26 (14)
C1—C6—C7—C8	−12.5 (2)	C11—C16—C17—C18	−16.6 (2)
O1—C7—C8—N1	−179.89 (14)	O6—C17—C18—N2	−177.69 (13)
C6—C7—C8—N1	0.0 (2)	C16—C17—C18—N2	3.8 (2)
O1—C7—C8—C9	−3.0 (2)	O6—C17—C18—C19	2.6 (2)
C6—C7—C8—C9	176.87 (13)	C16—C17—C18—C19	−175.92 (13)
S1—N1—C8—C7	34.08 (19)	S2—N2—C18—C17	34.94 (19)
S1—N1—C8—C9	−142.91 (12)	S2—N2—C18—C19	−145.32 (12)
C10—O5—C9—O4	−3.7 (2)	C20—O10—C19—O9	2.1 (2)
C10—O5—C9—C8	176.75 (13)	C20—O10—C19—C18	−176.20 (13)
C7—C8—C9—O4	3.3 (2)	C17—C18—C19—O9	−5.4 (2)
N1—C8—C9—O4	−179.71 (14)	N2—C18—C19—O9	174.86 (14)
C7—C8—C9—O5	−177.16 (13)	C17—C18—C19—O10	172.87 (14)
N1—C8—C9—O5	−0.17 (19)	N2—C18—C19—O10	−6.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.81 (2)	1.86 (2)	2.600 (2)	152 (2)
N1—H1N···O9	0.81 (2)	2.22 (2)	2.994 (2)	162 (2)
O6—H6O···O9	0.81 (2)	1.91 (2)	2.634 (2)	147 (2)
N2—H2N···O3ⁱ	0.83 (2)	2.13 (2)	2.966 (2)	175 (2)
C4—H4···O8ⁱⁱ	0.95	2.36	3.259 (2)	158
C20—H20A···O2ⁱ	0.98	2.51	3.267 (2)	134

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

Experimental details

Crystal data
Chemical formula	C₁₀H₉NO₅S
M_r	255.24
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.777 (2), 10.932 (4), 12.890 (4)
α, β, γ (°)	105.569 (16), 94.588 (15), 97.763 (16)
V (Å³)	1038.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.24 × 0.22 × 0.16

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.927, 0.950
No. of measured, independent and observed [(I) > 2.0 σ(I)] reflections	8716, 4693, 4191
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.03
No. of reflections	4693
No. of parameters	321
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.41

Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.81 (2)	1.86 (2)	2.600 (2)	152 (2)
N1—H1N···O9	0.81 (2)	2.22 (2)	2.994 (2)	162 (2)
O6—H6O···O9	0.81 (2)	1.91 (2)	2.634 (2)	147 (2)
N2—H2N···O3ⁱ	0.83 (2)	2.13 (2)	2.966 (2)	175 (2)
C4—H4···O8ⁱⁱ	0.95	2.36	3.259 (2)	158
C20—H20A···O2ⁱ	0.98	2.51	3.267 (2)	134

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

References

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