Methyl 4-hy-droxy-2-meth-oxy-carbonyl-methyl-1,1-dioxo-1,2-dihydro-1λ,2-benzothia-zine-3-carboxyl-ate.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(13)H(13)NO(7)S, which have almost identical geometries. The thia-zine ring adopts a sofa conformation in both mol-ecules and the mol-ecular conformations are stabilized by intramolecular O-H⋯O hydrogen bonds. Inter-molecular 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 = 327.30

Triclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.06

6923 reflections

407 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.42 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034921/bt5629sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811034921/bt5629Isup3.cml

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

C13H13NO7S	Z = 4
Mr = 327.30	F(000) = 680
Triclinic, P1	Dx = 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

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	Rint = 0.018
φ and ω scans	θmax = 28.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.882, Tmax = 0.917	k = −16→16
17331 measured reflections	l = −18→17

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(Fo2) + (0.0516P)2 + 0.9585P] where P = (Fo2 + 2Fc2)/3
6923 reflections	(Δ/σ)max = 0.001
407 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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.

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) ; (ii) .