3-Benzoyl-4-hydr-oxy-2H-1,2-benzothia-zine 1,1-dioxide.

There are two mol-ecules in the asymmetric unit of the title compound, C(15)H(11)NO(4)S. The heterocyclic thia-zine rings in both mol-ecules adopt half-chair conformations with the S and N atoms displaced by 0.455 (4) and 0.254 (4) Å, respectively, in one mol-ecule, and 0.480 (4) and 0.224 (5) Å in the other, on opposite sides of the mean planes formed by the remaining ring atoms. The crystal structure is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds. In addition, intra-molecular O-H⋯O inter-actions are also present.

Related literature

For the biological activity of 1,2-benzothia­zine derivatives, see: Ahmad et al. (2010 ▶); Lombardino et al. (1971 ▶, 1973 ▶). For the synthesis of benzothia­zine derivatives, see: Siddiqui et al. (2007 ▶). For comparison of bond distancess, see: Allen (2002 ▶). For related structures, see: Siddiqui et al. (2008 ▶)

Experimental

Crystal data

C15H11NO4S

M = 301.31

Monoclinic,

a = 13.8675 (4) Å

b = 7.6289 (2) Å

c = 25.7553 (9) Å

β = 102.4519 (12)°

V = 2660.66 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.12 × 0.11 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.970, T max = 0.980

10424 measured reflections

5971 independent reflections

5100 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.119

S = 1.09

5971 reflections

391 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.45 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009359/jh2134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009359/jh2134Isup2.hkl

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

C15H11NO4S	F(000) = 1248
Mr = 301.31	Dx = 1.504 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5113 reflections
a = 13.8675 (4) Å	θ = 1.0–27.5°
b = 7.6289 (2) Å	µ = 0.26 mm−1
c = 25.7553 (9) Å	T = 173 K
β = 102.4519 (12)°	Block, yellow
V = 2660.66 (14) Å3	0.12 × 0.11 × 0.08 mm
Z = 8

Nonius KappaCCD diffractometer	5971 independent reflections
Radiation source: fine-focus sealed tube	5100 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω and φ scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −17→18
Tmin = 0.970, Tmax = 0.980	k = −9→9
10424 measured reflections	l = −33→33

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0348P)2 + 2.7188P] where P = (Fo2 + 2Fc2)/3
5971 reflections	(Δ/σ)max < 0.001
391 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.44 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 > 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.

	x	y	z	Uiso*/Ueq
S1	0.26603 (4)	0.49396 (7)	−0.15139 (2)	0.02569 (13)
S2	0.26612 (4)	0.00960 (7)	0.14780 (2)	0.02805 (13)
O1	0.34849 (11)	0.3951 (2)	−0.16022 (6)	0.0392 (4)
O2	0.26099 (11)	0.6780 (2)	−0.16221 (6)	0.0338 (4)
O3	−0.00584 (11)	0.5375 (2)	−0.10052 (6)	0.0344 (4)
H3O	0.0138 (19)	0.580 (3)	−0.0643 (12)	0.041*
O4	0.08737 (11)	0.6136 (2)	−0.01058 (6)	0.0365 (4)
O5	0.24183 (12)	0.1891 (2)	0.15448 (6)	0.0367 (4)
O6	0.20854 (12)	−0.1254 (2)	0.16478 (6)	0.0362 (4)
O7	0.49817 (12)	0.1805 (2)	0.07325 (7)	0.0386 (4)
H7O	0.467 (2)	0.200 (4)	0.0367 (12)	0.046*
O8	0.37534 (12)	0.1864 (2)	−0.01398 (6)	0.0392 (4)
N1	0.25817 (13)	0.4634 (2)	−0.08997 (7)	0.0255 (4)
H1N	0.2839 (18)	0.370 (3)	−0.0763 (10)	0.031*
N2	0.26406 (13)	−0.0224 (2)	0.08502 (7)	0.0277 (4)
H2N	0.2516 (18)	−0.123 (4)	0.0752 (10)	0.033*
C1	0.15563 (15)	0.4015 (3)	−0.18693 (8)	0.0257 (4)
C2	0.15101 (18)	0.3292 (3)	−0.23688 (9)	0.0333 (5)
H2	0.2086	0.3204	−0.2511	0.040*
C3	0.0605 (2)	0.2700 (3)	−0.26569 (9)	0.0401 (6)
H3	0.0557	0.2224	−0.3002	0.048*
C4	−0.02274 (19)	0.2799 (3)	−0.24437 (9)	0.0391 (6)
H4	−0.0841	0.2378	−0.2643	0.047*
C5	−0.01775 (17)	0.3508 (3)	−0.19421 (9)	0.0322 (5)
H5	−0.0753	0.3561	−0.1799	0.039*
C6	0.07235 (15)	0.4143 (3)	−0.16478 (8)	0.0254 (4)
C7	0.07853 (15)	0.4912 (3)	−0.11193 (8)	0.0252 (4)
C8	0.16798 (14)	0.5127 (3)	−0.07560 (8)	0.0237 (4)
C9	0.16839 (15)	0.5735 (3)	−0.02290 (8)	0.0259 (4)
C10	0.25834 (14)	0.5793 (3)	0.02069 (8)	0.0244 (4)
C11	0.24653 (16)	0.5335 (3)	0.07145 (8)	0.0281 (4)
H11	0.1836	0.4978	0.0765	0.034*
C12	0.32640 (16)	0.5397 (3)	0.11451 (9)	0.0310 (5)
H12	0.3182	0.5073	0.1489	0.037*
C13	0.41781 (16)	0.5932 (3)	0.10724 (9)	0.0334 (5)
H13	0.4724	0.5978	0.1367	0.040*
C14	0.43023 (16)	0.6402 (3)	0.05692 (9)	0.0349 (5)
H14	0.4931	0.6778	0.0523	0.042*
C15	0.35116 (16)	0.6326 (3)	0.01342 (9)	0.0306 (5)
H15	0.3600	0.6633	−0.0210	0.037*
C16	0.39179 (16)	−0.0183 (3)	0.17731 (8)	0.0273 (4)
C17	0.42052 (18)	−0.0878 (3)	0.22798 (9)	0.0325 (5)
H17	0.3726	−0.1277	0.2466	0.039*
C18	0.52034 (18)	−0.0982 (3)	0.25096 (9)	0.0375 (5)
H18	0.5414	−0.1462	0.2856	0.045*
C19	0.58960 (18)	−0.0385 (3)	0.22344 (10)	0.0390 (5)
H19	0.6579	−0.0447	0.2397	0.047*
C20	0.56077 (17)	0.0299 (3)	0.17279 (9)	0.0345 (5)
H20	0.6091	0.0712	0.1546	0.041*
C21	0.46065 (16)	0.0384 (3)	0.14820 (8)	0.0270 (4)
C22	0.42919 (16)	0.0983 (3)	0.09300 (9)	0.0277 (4)
C23	0.33618 (15)	0.0685 (3)	0.06266 (8)	0.0263 (4)
C24	0.31153 (16)	0.1149 (3)	0.00718 (9)	0.0293 (4)
C25	0.21394 (16)	0.0753 (3)	−0.02777 (8)	0.0279 (4)
C26	0.21372 (17)	0.0020 (3)	−0.07754 (9)	0.0322 (5)
H26	0.2744	−0.0279	−0.0868	0.039*
C27	0.12542 (19)	−0.0269 (3)	−0.11332 (9)	0.0380 (5)
H27	0.1252	−0.0804	−0.1466	0.046*
C28	0.03701 (18)	0.0222 (3)	−0.10051 (10)	0.0368 (5)
H28	−0.0236	0.0037	−0.1253	0.044*
C29	0.03689 (17)	0.0983 (3)	−0.05150 (10)	0.0355 (5)
H29	−0.0237	0.1342	−0.0432	0.043*
C30	0.12487 (16)	0.1219 (3)	−0.01456 (9)	0.0309 (5)
H30	0.1245	0.1695	0.0195	0.037*

	U11	U22	U33	U12	U13	U23
S1	0.0246 (3)	0.0329 (3)	0.0208 (2)	−0.0011 (2)	0.00740 (19)	0.00065 (19)
S2	0.0320 (3)	0.0295 (3)	0.0255 (3)	−0.0025 (2)	0.0125 (2)	0.0031 (2)
O1	0.0309 (8)	0.0580 (11)	0.0314 (8)	0.0087 (8)	0.0122 (7)	−0.0032 (8)
O2	0.0362 (8)	0.0348 (8)	0.0305 (8)	−0.0102 (7)	0.0072 (7)	0.0043 (7)
O3	0.0214 (7)	0.0516 (10)	0.0303 (8)	0.0001 (7)	0.0057 (6)	−0.0036 (7)
O4	0.0257 (8)	0.0555 (10)	0.0299 (8)	0.0021 (7)	0.0096 (6)	−0.0074 (7)
O5	0.0463 (9)	0.0317 (8)	0.0369 (9)	0.0050 (7)	0.0196 (7)	0.0028 (7)
O6	0.0373 (9)	0.0413 (9)	0.0326 (8)	−0.0091 (7)	0.0133 (7)	0.0082 (7)
O7	0.0328 (8)	0.0504 (10)	0.0343 (9)	−0.0122 (8)	0.0114 (7)	0.0062 (8)
O8	0.0379 (9)	0.0531 (10)	0.0296 (8)	−0.0098 (8)	0.0138 (7)	0.0070 (7)
N1	0.0236 (8)	0.0339 (9)	0.0192 (8)	0.0037 (7)	0.0052 (6)	0.0028 (7)
N2	0.0320 (10)	0.0278 (9)	0.0252 (9)	−0.0069 (8)	0.0101 (7)	0.0008 (7)
C1	0.0305 (10)	0.0254 (10)	0.0206 (9)	−0.0019 (8)	0.0043 (8)	0.0022 (8)
C2	0.0451 (13)	0.0304 (11)	0.0253 (11)	−0.0003 (10)	0.0096 (9)	−0.0007 (9)
C3	0.0595 (16)	0.0334 (12)	0.0246 (11)	−0.0095 (11)	0.0029 (10)	−0.0048 (9)
C4	0.0473 (14)	0.0322 (12)	0.0320 (12)	−0.0120 (10)	−0.0047 (10)	−0.0006 (9)
C5	0.0332 (11)	0.0314 (11)	0.0294 (11)	−0.0074 (9)	0.0011 (9)	0.0053 (9)
C6	0.0290 (10)	0.0226 (10)	0.0237 (10)	−0.0032 (8)	0.0036 (8)	0.0032 (8)
C7	0.0249 (10)	0.0275 (10)	0.0242 (10)	−0.0024 (8)	0.0077 (8)	0.0041 (8)
C8	0.0226 (9)	0.0285 (10)	0.0207 (9)	−0.0001 (8)	0.0064 (7)	0.0025 (8)
C9	0.0239 (10)	0.0294 (10)	0.0247 (10)	−0.0030 (8)	0.0062 (8)	0.0002 (8)
C10	0.0246 (10)	0.0270 (10)	0.0222 (10)	−0.0026 (8)	0.0064 (8)	−0.0020 (8)
C11	0.0304 (11)	0.0291 (10)	0.0257 (10)	−0.0052 (8)	0.0081 (8)	−0.0016 (8)
C12	0.0350 (11)	0.0323 (11)	0.0241 (10)	−0.0024 (9)	0.0025 (9)	0.0039 (8)
C13	0.0295 (11)	0.0357 (12)	0.0313 (12)	−0.0021 (9)	−0.0019 (9)	0.0002 (9)
C14	0.0257 (10)	0.0437 (13)	0.0353 (12)	−0.0075 (10)	0.0067 (9)	−0.0025 (10)
C15	0.0299 (11)	0.0372 (12)	0.0259 (10)	−0.0064 (9)	0.0089 (9)	−0.0007 (9)
C16	0.0327 (11)	0.0238 (10)	0.0262 (10)	−0.0042 (8)	0.0085 (8)	−0.0033 (8)
C17	0.0428 (12)	0.0281 (11)	0.0274 (11)	−0.0034 (9)	0.0098 (9)	0.0017 (9)
C18	0.0494 (15)	0.0318 (12)	0.0282 (11)	−0.0005 (10)	0.0018 (10)	0.0030 (9)
C19	0.0361 (12)	0.0381 (13)	0.0394 (13)	0.0030 (10)	0.0005 (10)	−0.0020 (10)
C20	0.0351 (12)	0.0343 (12)	0.0352 (12)	−0.0036 (9)	0.0103 (10)	−0.0059 (10)
C21	0.0326 (11)	0.0237 (10)	0.0258 (10)	−0.0029 (8)	0.0090 (8)	−0.0026 (8)
C22	0.0316 (11)	0.0262 (10)	0.0282 (11)	−0.0041 (8)	0.0128 (9)	−0.0019 (8)
C23	0.0304 (10)	0.0264 (10)	0.0252 (10)	−0.0027 (8)	0.0128 (8)	0.0000 (8)
C24	0.0344 (11)	0.0288 (11)	0.0270 (11)	−0.0014 (9)	0.0113 (9)	−0.0006 (8)
C25	0.0357 (11)	0.0242 (10)	0.0253 (10)	−0.0021 (8)	0.0101 (9)	0.0043 (8)
C26	0.0359 (12)	0.0363 (12)	0.0261 (11)	0.0039 (9)	0.0107 (9)	0.0013 (9)
C27	0.0462 (14)	0.0391 (13)	0.0272 (11)	0.0012 (11)	0.0050 (10)	−0.0018 (10)
C28	0.0369 (12)	0.0381 (13)	0.0334 (12)	−0.0016 (10)	0.0029 (10)	0.0073 (10)
C29	0.0342 (12)	0.0343 (12)	0.0409 (13)	0.0023 (10)	0.0148 (10)	0.0094 (10)
C30	0.0378 (12)	0.0283 (11)	0.0292 (11)	−0.0003 (9)	0.0130 (9)	0.0017 (9)

S1—O1	1.4283 (16)	C11—C12	1.389 (3)
S1—O2	1.4303 (17)	C11—H11	0.9500
S1—N1	1.6257 (17)	C12—C13	1.382 (3)
S1—C1	1.753 (2)	C12—H12	0.9500
S2—O6	1.4281 (16)	C13—C14	1.391 (3)
S2—O5	1.4296 (17)	C13—H13	0.9500
S2—N2	1.6294 (19)	C14—C15	1.390 (3)
S2—C16	1.757 (2)	C14—H14	0.9500
O3—C7	1.314 (2)	C15—H15	0.9500
O3—H3O	0.97 (3)	C16—C17	1.385 (3)
O4—C9	1.269 (2)	C16—C21	1.404 (3)
O7—C22	1.333 (2)	C17—C18	1.385 (3)
O7—H7O	0.96 (3)	C17—H17	0.9500
O8—C24	1.259 (3)	C18—C19	1.388 (3)
N1—C8	1.429 (2)	C18—H18	0.9500
N1—H1N	0.84 (3)	C19—C20	1.382 (3)
N2—C23	1.436 (3)	C19—H19	0.9500
N2—H2N	0.82 (3)	C20—C21	1.398 (3)
C1—C2	1.389 (3)	C20—H20	0.9500
C1—C6	1.397 (3)	C21—C22	1.467 (3)
C2—C3	1.389 (3)	C22—C23	1.375 (3)
C2—H2	0.9500	C23—C24	1.440 (3)
C3—C4	1.383 (4)	C24—C25	1.486 (3)
C3—H3	0.9500	C25—C30	1.396 (3)
C4—C5	1.388 (3)	C25—C26	1.398 (3)
C4—H4	0.9500	C26—C27	1.382 (3)
C5—C6	1.401 (3)	C26—H26	0.9500
C5—H5	0.9500	C27—C28	1.388 (3)
C6—C7	1.468 (3)	C27—H27	0.9500
C7—C8	1.393 (3)	C28—C29	1.390 (3)
C8—C9	1.433 (3)	C28—H28	0.9500
C9—C10	1.488 (3)	C29—C30	1.388 (3)
C10—C11	1.397 (3)	C29—H29	0.9500
C10—C15	1.400 (3)	C30—H30	0.9500
O1—S1—O2	119.62 (10)	C11—C12—H12	120.0
O1—S1—N1	107.65 (10)	C12—C13—C14	120.2 (2)
O2—S1—N1	108.64 (10)	C12—C13—H13	119.9
O1—S1—C1	110.09 (10)	C14—C13—H13	119.9
O2—S1—C1	107.01 (10)	C15—C14—C13	120.4 (2)
N1—S1—C1	102.49 (9)	C15—C14—H14	119.8
O6—S2—O5	119.47 (10)	C13—C14—H14	119.8
O6—S2—N2	107.73 (10)	C14—C15—C10	119.5 (2)
O5—S2—N2	107.98 (10)	C14—C15—H15	120.2
O6—S2—C16	110.37 (10)	C10—C15—H15	120.2
O5—S2—C16	107.55 (10)	C17—C16—C21	122.1 (2)
N2—S2—C16	102.38 (10)	C17—C16—S2	120.70 (17)
C7—O3—H3O	103.1 (15)	C21—C16—S2	117.20 (17)
C22—O7—H7O	103.9 (16)	C16—C17—C18	118.8 (2)
C8—N1—S1	117.40 (14)	C16—C17—H17	120.6
C8—N1—H1N	115.7 (17)	C18—C17—H17	120.6
S1—N1—H1N	114.6 (17)	C17—C18—C19	120.1 (2)
C23—N2—S2	117.47 (15)	C17—C18—H18	120.0
C23—N2—H2N	116.7 (18)	C19—C18—H18	120.0
S2—N2—H2N	114.0 (18)	C20—C19—C18	121.0 (2)
C2—C1—C6	121.9 (2)	C20—C19—H19	119.5
C2—C1—S1	120.28 (17)	C18—C19—H19	119.5
C6—C1—S1	117.65 (15)	C19—C20—C21	120.2 (2)
C1—C2—C3	118.7 (2)	C19—C20—H20	119.9
C1—C2—H2	120.7	C21—C20—H20	119.9
C3—C2—H2	120.7	C20—C21—C16	117.9 (2)
C4—C3—C2	120.4 (2)	C20—C21—C22	120.82 (19)
C4—C3—H3	119.8	C16—C21—C22	121.28 (19)
C2—C3—H3	119.8	O7—C22—C23	121.55 (19)
C3—C4—C5	120.8 (2)	O7—C22—C21	115.35 (19)
C3—C4—H4	119.6	C23—C22—C21	123.07 (18)
C5—C4—H4	119.6	C22—C23—N2	120.07 (18)
C4—C5—C6	119.9 (2)	C22—C23—C24	121.07 (18)
C4—C5—H5	120.1	N2—C23—C24	118.69 (19)
C6—C5—H5	120.1	O8—C24—C23	119.8 (2)
C1—C6—C5	118.30 (19)	O8—C24—C25	117.33 (19)
C1—C6—C7	121.23 (18)	C23—C24—C25	122.79 (18)
C5—C6—C7	120.46 (19)	C30—C25—C26	119.9 (2)
O3—C7—C8	121.67 (19)	C30—C25—C24	122.61 (19)
O3—C7—C6	115.97 (18)	C26—C25—C24	117.28 (19)
C8—C7—C6	122.37 (18)	C27—C26—C25	120.1 (2)
C7—C8—N1	119.84 (18)	C27—C26—H26	119.9
C7—C8—C9	119.69 (18)	C25—C26—H26	119.9
N1—C8—C9	120.35 (17)	C26—C27—C28	120.0 (2)
O4—C9—C8	119.47 (18)	C26—C27—H27	120.0
O4—C9—C10	116.58 (18)	C28—C27—H27	120.0
C8—C9—C10	123.76 (18)	C27—C28—C29	120.2 (2)
C11—C10—C15	119.64 (19)	C27—C28—H28	119.9
C11—C10—C9	116.76 (18)	C29—C28—H28	119.9
C15—C10—C9	123.57 (18)	C30—C29—C28	120.3 (2)
C12—C11—C10	120.3 (2)	C30—C29—H29	119.9
C12—C11—H11	119.8	C28—C29—H29	119.9
C10—C11—H11	119.8	C29—C30—C25	119.5 (2)
C13—C12—C11	119.9 (2)	C29—C30—H30	120.2
C13—C12—H12	120.0	C25—C30—H30	120.2
O1—S1—N1—C8	−164.69 (16)	C13—C14—C15—C10	0.9 (4)
O2—S1—N1—C8	64.40 (17)	C11—C10—C15—C14	−0.4 (3)
C1—S1—N1—C8	−48.61 (18)	C9—C10—C15—C14	177.5 (2)
O6—S2—N2—C23	−164.50 (16)	O6—S2—C16—C17	−33.0 (2)
O5—S2—N2—C23	65.20 (18)	O5—S2—C16—C17	98.90 (19)
C16—S2—N2—C23	−48.12 (18)	N2—S2—C16—C17	−147.47 (18)
O1—S1—C1—C2	−36.5 (2)	O6—S2—C16—C21	149.25 (16)
O2—S1—C1—C2	94.97 (19)	O5—S2—C16—C21	−78.84 (18)
N1—S1—C1—C2	−150.81 (18)	N2—S2—C16—C21	34.79 (18)
O1—S1—C1—C6	147.68 (16)	C21—C16—C17—C18	1.4 (3)
O2—S1—C1—C6	−80.85 (18)	S2—C16—C17—C18	−176.28 (17)
N1—S1—C1—C6	33.37 (18)	C16—C17—C18—C19	0.4 (3)
C6—C1—C2—C3	0.8 (3)	C17—C18—C19—C20	−0.8 (4)
S1—C1—C2—C3	−174.87 (17)	C18—C19—C20—C21	−0.6 (4)
C1—C2—C3—C4	−1.3 (4)	C19—C20—C21—C16	2.2 (3)
C2—C3—C4—C5	0.7 (4)	C19—C20—C21—C22	−175.4 (2)
C3—C4—C5—C6	0.5 (3)	C17—C16—C21—C20	−2.7 (3)
C2—C1—C6—C5	0.4 (3)	S2—C16—C21—C20	175.06 (16)
S1—C1—C6—C5	176.13 (16)	C17—C16—C21—C22	174.9 (2)
C2—C1—C6—C7	−180.0 (2)	S2—C16—C21—C22	−7.4 (3)
S1—C1—C6—C7	−4.2 (3)	C20—C21—C22—O7	−15.2 (3)
C4—C5—C6—C1	−1.0 (3)	C16—C21—C22—O7	167.30 (19)
C4—C5—C6—C7	179.4 (2)	C20—C21—C22—C23	163.1 (2)
C1—C6—C7—O3	163.40 (19)	C16—C21—C22—C23	−14.4 (3)
C5—C6—C7—O3	−17.0 (3)	O7—C22—C23—N2	179.2 (2)
C1—C6—C7—C8	−17.3 (3)	C21—C22—C23—N2	1.1 (3)
C5—C6—C7—C8	162.4 (2)	O7—C22—C23—C24	4.1 (3)
O3—C7—C8—N1	−178.91 (18)	C21—C22—C23—C24	−174.0 (2)
C6—C7—C8—N1	1.8 (3)	S2—N2—C23—C22	34.4 (3)
O3—C7—C8—C9	5.1 (3)	S2—N2—C23—C24	−150.31 (17)
C6—C7—C8—C9	−174.25 (19)	C22—C23—C24—O8	−1.1 (3)
S1—N1—C8—C7	35.2 (3)	N2—C23—C24—O8	−176.3 (2)
S1—N1—C8—C9	−148.77 (16)	C22—C23—C24—C25	176.2 (2)
C7—C8—C9—O4	−2.7 (3)	N2—C23—C24—C25	1.0 (3)
N1—C8—C9—O4	−178.73 (19)	O8—C24—C25—C30	−130.8 (2)
C7—C8—C9—C10	172.00 (19)	C23—C24—C25—C30	51.8 (3)
N1—C8—C9—C10	−4.0 (3)	O8—C24—C25—C26	43.7 (3)
O4—C9—C10—C11	33.7 (3)	C23—C24—C25—C26	−133.7 (2)
C8—C9—C10—C11	−141.1 (2)	C30—C25—C26—C27	−1.0 (3)
O4—C9—C10—C15	−144.3 (2)	C24—C25—C26—C27	−175.7 (2)
C8—C9—C10—C15	40.9 (3)	C25—C26—C27—C28	2.1 (4)
C15—C10—C11—C12	−0.3 (3)	C26—C27—C28—C29	−0.9 (4)
C9—C10—C11—C12	−178.4 (2)	C27—C28—C29—C30	−1.5 (3)
C10—C11—C12—C13	0.6 (3)	C28—C29—C30—C25	2.6 (3)
C11—C12—C13—C14	−0.2 (4)	C26—C25—C30—C29	−1.3 (3)
C12—C13—C14—C15	−0.6 (4)	C24—C25—C30—C29	173.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O8	0.84 (3)	2.30 (3)	3.093 (3)	159 (2)
O3—H3O···O4	0.97 (3)	1.55 (3)	2.466 (2)	155 (2)
O7—H7O···O8	0.96 (3)	1.62 (3)	2.510 (2)	153 (3)
C2—H2···O5i	0.95	2.57	3.310 (3)	135
C13—H13···O1ii	0.95	2.43	3.235 (3)	143
C14—H14···O8ii	0.95	2.48	3.396 (3)	162
C15—H15···N1	0.95	2.53	2.990 (3)	110

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O8	0.84 (3)	2.30 (3)	3.093 (3)	159 (2)
O3—H3O⋯O4	0.97 (3)	1.55 (3)	2.466 (2)	155 (2)
O7—H7O⋯O8	0.96 (3)	1.62 (3)	2.510 (2)	153 (3)
C2—H2⋯O5i	0.95	2.57	3.310 (3)	135
C13—H13⋯O1ii	0.95	2.43	3.235 (3)	143
C14—H14⋯O8ii	0.95	2.48	3.396 (3)	162

Symmetry codes: (i) ; (ii) .