N-(2-Chloro-phen-yl)-4-hydr-oxy-2H-1,2-benzothia-zine-3-carboxamide 1,1-dioxide.

In the title compound, C(15)H(11)ClN(2)O(4)S, there are two independent mol-ecules in the asymmetric unit, in which the heterocyclic thia-zine rings in both mol-ecules adopt half-chair conformations. The conformations about the C-C and C-N bonds in the central C-C-N-C chain in both mol-ecules are all EZ. There are strong intra-molecular O-H⋯O and N-H⋯N hydrogen bonds resulting in graph-set patterns S(6) and S(5) for the oxo and amino rings, in addition to intra-molecular N-H⋯Cl inter-actions. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds into chains along [100].

Related literature

For details of the synthesis, see: Siddiqui et al. (2008 ▶). For background to benzothia­zine carboxamide derivatives as analgesic and anti-inflammatory agents, see: Myung et al. (2002 ▶); Shin et al. (2000 ▶); Banerjee & Sarkar (2002 ▶). For related structures, see: Siddiqui et al. (2006 ▶, 2007 ▶, 2008 ▶). Allen et al. (1987 ▶). For hydrogen-bond patterns and graph sets, see: Bernstein et al. (1994 ▶).

Experimental

Crystal data

C15H11ClN2O4S

M = 350.77

Monoclinic,

a = 10.077 (2) Å

b = 13.818 (3) Å

c = 21.426 (4) Å

β = 97.070 (13)°

V = 2960.8 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.42 mm−1

T = 200 K

0.16 × 0.14 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.936, T max = 0.951

12965 measured reflections

6732 independent reflections

5711 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.101

S = 1.05

6732 reflections

433 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.39 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/S1600536809033972/lh2886sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033972/lh2886Isup2.hkl

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

C15H11ClN2O4S	F(000) = 1440
Mr = 350.77	Dx = 1.574 Mg m−3
Monoclinic, P21/c	Melting point = 491–492 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.077 (2) Å	Cell parameters from 12965 reflections
b = 13.818 (3) Å	θ = 2.8–27.5°
c = 21.426 (4) Å	µ = 0.42 mm−1
β = 97.070 (13)°	T = 200 K
V = 2960.8 (10) Å3	Block, colorless
Z = 8	0.16 × 0.14 × 0.12 mm

Nonius KappaCCD diffractometer	6732 independent reflections
Radiation source: fine-focus sealed tube	5711 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω and φ scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −13→13
Tmin = 0.936, Tmax = 0.951	k = −17→17
12965 measured reflections	l = −27→27

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.032P)2 + 2.78P] where P = (Fo2 + 2Fc2)/3
6732 reflections	(Δ/σ)max = 0.001
433 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.53894 (6)	0.85003 (4)	0.44704 (3)	0.03897 (14)
Cl2	1.01898 (6)	0.42658 (4)	0.72988 (3)	0.03888 (14)
S1	0.56632 (5)	0.56337 (4)	0.29991 (2)	0.02616 (11)
S2	0.88023 (5)	0.18009 (4)	0.55861 (2)	0.02725 (12)
O1	0.42471 (14)	0.56870 (11)	0.28299 (7)	0.0345 (3)
O2	0.65098 (16)	0.63267 (11)	0.27504 (7)	0.0376 (4)
O3	0.91579 (14)	0.44058 (11)	0.40450 (7)	0.0306 (3)
H3O	0.942 (3)	0.475 (2)	0.4358 (13)	0.046*
O4	0.90157 (13)	0.58281 (10)	0.48371 (7)	0.0299 (3)
O5	1.01519 (15)	0.14585 (11)	0.56604 (8)	0.0394 (4)
O6	0.79336 (16)	0.15325 (11)	0.60351 (7)	0.0361 (3)
O7	0.55675 (14)	0.35003 (11)	0.46691 (7)	0.0316 (3)
H7O	0.552 (3)	0.405 (2)	0.4885 (13)	0.047*
O8	0.62498 (14)	0.48103 (10)	0.55245 (6)	0.0285 (3)
N1	0.59401 (16)	0.56899 (12)	0.37671 (8)	0.0246 (3)
H1N	0.527 (2)	0.5434 (17)	0.3934 (11)	0.030*
N2	0.72054 (17)	0.68431 (12)	0.46688 (8)	0.0273 (4)
H2N	0.653 (2)	0.6924 (17)	0.4419 (11)	0.033*
N3	0.88570 (16)	0.29841 (12)	0.55636 (8)	0.0256 (3)
H3N	0.956 (2)	0.3194 (17)	0.5386 (11)	0.031*
N4	0.81507 (17)	0.45318 (12)	0.62112 (8)	0.0259 (3)
H4N	0.881 (2)	0.4116 (17)	0.6302 (11)	0.031*
C1	0.7962 (2)	0.32702 (15)	0.30815 (10)	0.0331 (5)
H1	0.8737	0.3034	0.3333	0.040*
C2	0.7414 (2)	0.27512 (17)	0.25567 (11)	0.0384 (5)
H2	0.7817	0.2161	0.2452	0.046*
C3	0.6289 (2)	0.30844 (17)	0.21865 (10)	0.0380 (5)
H3	0.5912	0.2716	0.1834	0.046*
C4	0.5707 (2)	0.39514 (16)	0.23257 (10)	0.0339 (5)
H4	0.4937	0.4185	0.2069	0.041*
C5	0.6264 (2)	0.44760 (14)	0.28448 (9)	0.0255 (4)
C6	0.73784 (19)	0.41364 (14)	0.32404 (9)	0.0248 (4)
C7	0.79336 (18)	0.46879 (14)	0.38005 (8)	0.0227 (4)
C8	0.72638 (18)	0.54292 (14)	0.40405 (9)	0.0235 (4)
C9	0.78939 (19)	0.60425 (14)	0.45506 (9)	0.0235 (4)
C10	0.75144 (19)	0.75747 (14)	0.51204 (9)	0.0256 (4)
C11	0.6697 (2)	0.83982 (15)	0.50801 (10)	0.0298 (4)
C12	0.6902 (2)	0.91379 (16)	0.55174 (11)	0.0391 (5)
H12	0.6331	0.9687	0.5486	0.047*
C13	0.7943 (3)	0.90723 (17)	0.60010 (11)	0.0411 (5)
H13	0.8091	0.9575	0.6304	0.049*
C14	0.8764 (2)	0.82715 (17)	0.60399 (11)	0.0391 (5)
H14	0.9487	0.8233	0.6369	0.047*
C15	0.8559 (2)	0.75196 (16)	0.56085 (10)	0.0326 (5)
H15	0.9129	0.6970	0.5647	0.039*
C16	0.6273 (2)	0.19136 (17)	0.39968 (10)	0.0375 (5)
H16	0.5581	0.2327	0.3811	0.045*
C17	0.6553 (3)	0.10598 (19)	0.36988 (11)	0.0454 (6)
H17	0.6051	0.0894	0.3309	0.054*
C18	0.7550 (3)	0.04472 (18)	0.39617 (11)	0.0430 (6)
H18	0.7738	−0.0131	0.3749	0.052*
C19	0.8279 (2)	0.06714 (16)	0.45352 (11)	0.0361 (5)
H19	0.8957	0.0247	0.4722	0.043*
C20	0.7998 (2)	0.15269 (14)	0.48302 (9)	0.0266 (4)
C21	0.7005 (2)	0.21657 (14)	0.45671 (9)	0.0259 (4)
C22	0.67419 (19)	0.30822 (14)	0.48818 (9)	0.0244 (4)
C23	0.76116 (18)	0.34608 (14)	0.53550 (9)	0.0233 (4)
C24	0.72824 (18)	0.43260 (14)	0.57014 (9)	0.0239 (4)
C25	0.81369 (19)	0.52796 (14)	0.66608 (9)	0.0260 (4)
C26	0.9062 (2)	0.52284 (15)	0.72014 (9)	0.0300 (4)
C27	0.9109 (2)	0.59287 (18)	0.76655 (10)	0.0398 (5)
H27	0.9747	0.5883	0.8030	0.048*
C28	0.8223 (3)	0.66939 (18)	0.75945 (11)	0.0430 (6)
H28	0.8241	0.7174	0.7913	0.052*
C29	0.7307 (2)	0.67612 (16)	0.70588 (12)	0.0403 (5)
H29	0.6705	0.7293	0.7011	0.048*
C30	0.7255 (2)	0.60632 (15)	0.65903 (10)	0.0331 (5)
H30	0.6625	0.6118	0.6224	0.040*

	U11	U22	U33	U12	U13	U23
Cl1	0.0360 (3)	0.0319 (3)	0.0464 (3)	0.0097 (2)	−0.0055 (2)	0.0013 (2)
Cl2	0.0392 (3)	0.0409 (3)	0.0342 (3)	0.0065 (2)	−0.0048 (2)	0.0003 (2)
S1	0.0264 (2)	0.0246 (2)	0.0261 (2)	0.00015 (19)	−0.00253 (18)	0.00546 (19)
S2	0.0291 (3)	0.0255 (2)	0.0263 (2)	0.00761 (19)	−0.00002 (18)	−0.00181 (19)
O1	0.0272 (8)	0.0375 (8)	0.0357 (8)	0.0038 (6)	−0.0079 (6)	0.0052 (7)
O2	0.0430 (9)	0.0289 (8)	0.0412 (8)	−0.0027 (7)	0.0064 (7)	0.0130 (7)
O3	0.0240 (7)	0.0338 (8)	0.0318 (7)	0.0074 (6)	−0.0048 (6)	−0.0051 (6)
O4	0.0238 (7)	0.0311 (8)	0.0325 (7)	0.0060 (6)	−0.0054 (6)	−0.0056 (6)
O5	0.0329 (8)	0.0378 (9)	0.0453 (9)	0.0164 (7)	−0.0044 (7)	−0.0066 (7)
O6	0.0456 (9)	0.0340 (8)	0.0293 (7)	0.0036 (7)	0.0066 (6)	0.0025 (6)
O7	0.0269 (7)	0.0305 (8)	0.0350 (8)	0.0057 (6)	−0.0059 (6)	−0.0003 (6)
O8	0.0247 (7)	0.0279 (7)	0.0320 (7)	0.0065 (6)	0.0004 (5)	−0.0014 (6)
N1	0.0208 (8)	0.0267 (8)	0.0255 (8)	0.0011 (6)	−0.0004 (6)	0.0007 (7)
N2	0.0253 (9)	0.0258 (8)	0.0289 (8)	0.0041 (7)	−0.0037 (7)	−0.0022 (7)
N3	0.0201 (8)	0.0247 (8)	0.0312 (8)	0.0039 (6)	−0.0005 (6)	−0.0031 (7)
N4	0.0227 (8)	0.0243 (8)	0.0299 (8)	0.0043 (7)	0.0001 (6)	−0.0042 (7)
C1	0.0342 (11)	0.0307 (11)	0.0338 (11)	0.0055 (9)	0.0019 (8)	−0.0029 (9)
C2	0.0466 (14)	0.0315 (11)	0.0373 (11)	0.0017 (10)	0.0057 (10)	−0.0073 (9)
C3	0.0478 (14)	0.0359 (12)	0.0296 (10)	−0.0062 (10)	0.0019 (9)	−0.0079 (9)
C4	0.0372 (12)	0.0353 (11)	0.0272 (10)	−0.0038 (9)	−0.0034 (8)	0.0015 (9)
C5	0.0280 (10)	0.0247 (9)	0.0234 (9)	−0.0016 (8)	0.0013 (7)	0.0035 (7)
C6	0.0243 (9)	0.0251 (9)	0.0248 (9)	−0.0014 (7)	0.0026 (7)	0.0013 (7)
C7	0.0196 (9)	0.0245 (9)	0.0233 (9)	0.0008 (7)	0.0004 (7)	0.0028 (7)
C8	0.0190 (9)	0.0257 (9)	0.0249 (9)	0.0006 (7)	−0.0008 (7)	0.0014 (7)
C9	0.0225 (9)	0.0230 (9)	0.0244 (9)	0.0000 (7)	0.0015 (7)	0.0015 (7)
C10	0.0273 (10)	0.0226 (9)	0.0271 (9)	−0.0005 (8)	0.0042 (7)	−0.0007 (8)
C11	0.0305 (11)	0.0269 (10)	0.0317 (10)	0.0022 (8)	0.0029 (8)	0.0022 (8)
C12	0.0465 (14)	0.0245 (10)	0.0466 (13)	0.0066 (9)	0.0069 (10)	−0.0024 (9)
C13	0.0544 (15)	0.0286 (11)	0.0394 (12)	−0.0002 (10)	0.0021 (10)	−0.0090 (10)
C14	0.0455 (13)	0.0371 (12)	0.0325 (11)	0.0003 (10)	−0.0038 (9)	−0.0065 (9)
C15	0.0351 (11)	0.0295 (11)	0.0321 (10)	0.0052 (9)	−0.0007 (8)	−0.0028 (9)
C16	0.0458 (13)	0.0359 (12)	0.0283 (10)	−0.0002 (10)	−0.0051 (9)	−0.0002 (9)
C17	0.0616 (16)	0.0451 (14)	0.0274 (11)	−0.0086 (12)	−0.0032 (10)	−0.0099 (10)
C18	0.0577 (16)	0.0365 (12)	0.0356 (12)	−0.0025 (11)	0.0093 (11)	−0.0143 (10)
C19	0.0377 (12)	0.0326 (11)	0.0388 (12)	0.0040 (9)	0.0077 (9)	−0.0066 (9)
C20	0.0283 (10)	0.0269 (10)	0.0247 (9)	0.0014 (8)	0.0040 (7)	−0.0035 (8)
C21	0.0288 (10)	0.0243 (9)	0.0244 (9)	−0.0013 (8)	0.0027 (7)	0.0003 (8)
C22	0.0218 (9)	0.0255 (9)	0.0257 (9)	0.0023 (7)	0.0018 (7)	0.0037 (8)
C23	0.0208 (9)	0.0221 (9)	0.0269 (9)	0.0040 (7)	0.0023 (7)	0.0004 (7)
C24	0.0223 (9)	0.0227 (9)	0.0268 (9)	0.0003 (7)	0.0038 (7)	0.0001 (7)
C25	0.0272 (10)	0.0229 (9)	0.0288 (9)	−0.0032 (8)	0.0075 (7)	−0.0030 (8)
C26	0.0314 (11)	0.0308 (10)	0.0286 (10)	−0.0021 (9)	0.0062 (8)	−0.0015 (8)
C27	0.0475 (14)	0.0412 (13)	0.0306 (11)	−0.0081 (11)	0.0047 (9)	−0.0087 (10)
C28	0.0542 (15)	0.0364 (12)	0.0400 (12)	−0.0059 (11)	0.0127 (11)	−0.0163 (10)
C29	0.0442 (14)	0.0283 (11)	0.0502 (13)	0.0024 (10)	0.0126 (11)	−0.0108 (10)
C30	0.0334 (11)	0.0277 (10)	0.0379 (11)	0.0014 (9)	0.0036 (9)	−0.0035 (9)

Cl1—C11	1.744 (2)	C6—C7	1.473 (3)
Cl2—C26	1.745 (2)	C7—C8	1.362 (3)
S1—O2	1.4284 (15)	C8—C9	1.465 (3)
S1—O1	1.4304 (15)	C10—C15	1.391 (3)
S1—N1	1.6368 (17)	C10—C11	1.401 (3)
S1—C5	1.756 (2)	C11—C12	1.385 (3)
S2—O6	1.4271 (16)	C12—C13	1.384 (3)
S2—O5	1.4302 (15)	C12—H12	0.9500
S2—N3	1.6368 (18)	C13—C14	1.378 (3)
S2—C20	1.761 (2)	C13—H13	0.9500
O3—C7	1.338 (2)	C14—C15	1.389 (3)
O3—H3O	0.83 (3)	C14—H14	0.9500
O4—C9	1.254 (2)	C15—H15	0.9500
O7—C22	1.345 (2)	C16—C17	1.387 (3)
O7—H7O	0.89 (3)	C16—C21	1.392 (3)
O8—C24	1.256 (2)	C16—H16	0.9500
N1—C8	1.435 (2)	C17—C18	1.380 (4)
N1—H1N	0.87 (2)	C17—H17	0.9500
N2—C9	1.346 (2)	C18—C19	1.387 (3)
N2—C10	1.408 (3)	C18—H18	0.9500
N2—H2N	0.82 (2)	C19—C20	1.386 (3)
N3—C23	1.439 (2)	C19—H19	0.9500
N3—H3N	0.89 (2)	C20—C21	1.400 (3)
N4—C24	1.343 (2)	C21—C22	1.474 (3)
N4—C25	1.414 (2)	C22—C23	1.361 (3)
N4—H4N	0.88 (2)	C23—C24	1.467 (3)
C1—C2	1.389 (3)	C25—C26	1.396 (3)
C1—C6	1.394 (3)	C25—C30	1.397 (3)
C1—H1	0.9500	C26—C27	1.384 (3)
C2—C3	1.380 (3)	C27—C28	1.380 (4)
C2—H2	0.9500	C27—H27	0.9500
C3—C4	1.382 (3)	C28—C29	1.385 (4)
C3—H3	0.9500	C28—H28	0.9500
C4—C5	1.387 (3)	C29—C30	1.388 (3)
C4—H4	0.9500	C29—H29	0.9500
C5—C6	1.402 (3)	C30—H30	0.9500
O2—S1—O1	119.61 (9)	C10—C11—Cl1	119.75 (16)
O2—S1—N1	107.91 (9)	C13—C12—C11	119.6 (2)
O1—S1—N1	107.08 (9)	C13—C12—H12	120.2
O2—S1—C5	107.76 (10)	C11—C12—H12	120.2
O1—S1—C5	110.81 (9)	C14—C13—C12	119.5 (2)
N1—S1—C5	102.26 (9)	C14—C13—H13	120.3
O6—S2—O5	119.52 (10)	C12—C13—H13	120.3
O6—S2—N3	107.77 (9)	C13—C14—C15	121.4 (2)
O5—S2—N3	107.38 (10)	C13—C14—H14	119.3
O6—S2—C20	108.25 (10)	C15—C14—H14	119.3
O5—S2—C20	110.78 (9)	C14—C15—C10	119.7 (2)
N3—S2—C20	101.59 (9)	C14—C15—H15	120.1
C7—O3—H3O	109.8 (19)	C10—C15—H15	120.1
C22—O7—H7O	107.0 (17)	C17—C16—C21	120.1 (2)
C8—N1—S1	115.68 (13)	C17—C16—H16	119.9
C8—N1—H1N	117.0 (15)	C21—C16—H16	119.9
S1—N1—H1N	110.4 (15)	C18—C17—C16	120.9 (2)
C9—N2—C10	130.09 (17)	C18—C17—H17	119.6
C9—N2—H2N	113.3 (17)	C16—C17—H17	119.6
C10—N2—H2N	116.5 (17)	C17—C18—C19	120.3 (2)
C23—N3—S2	115.79 (13)	C17—C18—H18	119.9
C23—N3—H3N	115.3 (15)	C19—C18—H18	119.9
S2—N3—H3N	111.6 (15)	C20—C19—C18	118.6 (2)
C24—N4—C25	130.44 (17)	C20—C19—H19	120.7
C24—N4—H4N	116.0 (15)	C18—C19—H19	120.7
C25—N4—H4N	113.4 (15)	C19—C20—C21	122.03 (19)
C2—C1—C6	120.2 (2)	C19—C20—S2	120.40 (16)
C2—C1—H1	119.9	C21—C20—S2	117.38 (15)
C6—C1—H1	119.9	C16—C21—C20	118.09 (19)
C3—C2—C1	120.6 (2)	C16—C21—C22	120.74 (19)
C3—C2—H2	119.7	C20—C21—C22	121.17 (17)
C1—C2—H2	119.7	O7—C22—C23	123.13 (18)
C2—C3—C4	120.3 (2)	O7—C22—C21	114.48 (17)
C2—C3—H3	119.8	C23—C22—C21	122.39 (17)
C4—C3—H3	119.8	C22—C23—N3	120.84 (17)
C3—C4—C5	119.1 (2)	C22—C23—C24	121.70 (17)
C3—C4—H4	120.5	N3—C23—C24	117.32 (16)
C5—C4—H4	120.5	O8—C24—N4	124.42 (18)
C4—C5—C6	121.64 (19)	O8—C24—C23	120.82 (17)
C4—C5—S1	120.83 (16)	N4—C24—C23	114.76 (16)
C6—C5—S1	117.38 (15)	C26—C25—C30	118.66 (19)
C1—C6—C5	118.06 (18)	C26—C25—N4	117.81 (18)
C1—C6—C7	120.92 (18)	C30—C25—N4	123.53 (19)
C5—C6—C7	121.01 (17)	C27—C26—C25	121.4 (2)
O3—C7—C8	123.19 (17)	C27—C26—Cl2	118.85 (17)
O3—C7—C6	114.07 (16)	C25—C26—Cl2	119.75 (16)
C8—C7—C6	122.73 (17)	C28—C27—C26	119.5 (2)
C7—C8—N1	120.91 (17)	C28—C27—H27	120.3
C7—C8—C9	121.83 (17)	C26—C27—H27	120.3
N1—C8—C9	117.07 (16)	C27—C28—C29	119.9 (2)
O4—C9—N2	123.81 (18)	C27—C28—H28	120.0
O4—C9—C8	120.71 (17)	C29—C28—H28	120.0
N2—C9—C8	115.45 (17)	C28—C29—C30	121.0 (2)
C15—C10—C11	118.37 (18)	C28—C29—H29	119.5
C15—C10—N2	124.07 (18)	C30—C29—H29	119.5
C11—C10—N2	117.55 (18)	C29—C30—C25	119.6 (2)
C12—C11—C10	121.4 (2)	C29—C30—H30	120.2
C12—C11—Cl1	118.89 (17)	C25—C30—H30	120.2
O2—S1—N1—C8	−63.66 (16)	C13—C14—C15—C10	0.8 (4)
O1—S1—N1—C8	166.37 (14)	C11—C10—C15—C14	0.1 (3)
C5—S1—N1—C8	49.81 (16)	N2—C10—C15—C14	−178.5 (2)
O6—S2—N3—C23	−63.06 (16)	C21—C16—C17—C18	0.3 (4)
O5—S2—N3—C23	166.96 (14)	C16—C17—C18—C19	0.9 (4)
C20—S2—N3—C23	50.61 (16)	C17—C18—C19—C20	−1.0 (4)
C6—C1—C2—C3	0.0 (3)	C18—C19—C20—C21	0.1 (3)
C1—C2—C3—C4	1.4 (4)	C18—C19—C20—S2	175.04 (18)
C2—C3—C4—C5	−0.5 (3)	O6—S2—C20—C19	−97.28 (19)
C3—C4—C5—C6	−1.7 (3)	O5—S2—C20—C19	35.6 (2)
C3—C4—C5—S1	173.86 (16)	N3—S2—C20—C19	149.40 (18)
O2—S1—C5—C4	−96.73 (18)	O6—S2—C20—C21	77.92 (18)
O1—S1—C5—C4	35.9 (2)	O5—S2—C20—C21	−149.22 (16)
N1—S1—C5—C4	149.69 (17)	N3—S2—C20—C21	−35.39 (18)
O2—S1—C5—C6	78.99 (17)	C17—C16—C21—C20	−1.2 (3)
O1—S1—C5—C6	−148.42 (15)	C17—C16—C21—C22	178.5 (2)
N1—S1—C5—C6	−34.59 (17)	C19—C20—C21—C16	1.1 (3)
C2—C1—C6—C5	−2.2 (3)	S2—C20—C21—C16	−174.06 (16)
C2—C1—C6—C7	179.0 (2)	C19—C20—C21—C22	−178.64 (19)
C4—C5—C6—C1	3.0 (3)	S2—C20—C21—C22	6.2 (3)
S1—C5—C6—C1	−172.66 (15)	C16—C21—C22—O7	16.3 (3)
C4—C5—C6—C7	−178.18 (18)	C20—C21—C22—O7	−163.96 (18)
S1—C5—C6—C7	6.1 (2)	C16—C21—C22—C23	−164.7 (2)
C1—C6—C7—O3	13.8 (3)	C20—C21—C22—C23	15.0 (3)
C5—C6—C7—O3	−164.97 (17)	O7—C22—C23—N3	−179.88 (17)
C1—C6—C7—C8	−167.18 (19)	C21—C22—C23—N3	1.2 (3)
C5—C6—C7—C8	14.1 (3)	O7—C22—C23—C24	4.5 (3)
O3—C7—C8—N1	−178.75 (17)	C21—C22—C23—C24	−174.39 (17)
C6—C7—C8—N1	2.3 (3)	S2—N3—C23—C22	−38.4 (2)
O3—C7—C8—C9	6.4 (3)	S2—N3—C23—C24	137.43 (15)
C6—C7—C8—C9	−172.57 (17)	C25—N4—C24—O8	1.1 (3)
S1—N1—C8—C7	−38.3 (2)	C25—N4—C24—C23	−177.98 (18)
S1—N1—C8—C9	136.81 (15)	C22—C23—C24—O8	−8.3 (3)
C10—N2—C9—O4	−2.1 (3)	N3—C23—C24—O8	175.95 (17)
C10—N2—C9—C8	179.71 (19)	C22—C23—C24—N4	170.83 (18)
C7—C8—C9—O4	−9.2 (3)	N3—C23—C24—N4	−4.9 (3)
N1—C8—C9—O4	175.77 (17)	C24—N4—C25—C26	169.9 (2)
C7—C8—C9—N2	169.08 (18)	C24—N4—C25—C30	−10.4 (3)
N1—C8—C9—N2	−6.0 (3)	C30—C25—C26—C27	0.6 (3)
C9—N2—C10—C15	−10.1 (3)	N4—C25—C26—C27	−179.67 (19)
C9—N2—C10—C11	171.3 (2)	C30—C25—C26—Cl2	−179.24 (16)
C15—C10—C11—C12	−0.9 (3)	N4—C25—C26—Cl2	0.5 (3)
N2—C10—C11—C12	177.8 (2)	C25—C26—C27—C28	0.1 (3)
C15—C10—C11—Cl1	179.31 (16)	Cl2—C26—C27—C28	−179.99 (18)
N2—C10—C11—Cl1	−2.0 (3)	C26—C27—C28—C29	−0.7 (4)
C10—C11—C12—C13	0.8 (3)	C27—C28—C29—C30	0.5 (4)
Cl1—C11—C12—C13	−179.42 (19)	C28—C29—C30—C25	0.2 (3)
C11—C12—C13—C14	0.1 (4)	C26—C25—C30—C29	−0.8 (3)
C12—C13—C14—C15	−0.9 (4)	N4—C25—C30—C29	179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.83 (3)	1.89 (3)	2.612 (2)	144 (3)
O3—H3O···O4i	0.83 (3)	2.33 (3)	2.854 (2)	122 (2)
O7—H7O···O8	0.89 (3)	1.81 (3)	2.607 (2)	147 (2)
O7—H7O···O8ii	0.89 (3)	2.46 (3)	2.964 (2)	116 (2)
N1—H1N···O8ii	0.87 (2)	2.06 (2)	2.911 (2)	164 (2)
N2—H2N···N1	0.82 (2)	2.24 (2)	2.700 (2)	116 (2)
N2—H2N···Cl1	0.82 (2)	2.47 (2)	2.930 (2)	116 (2)
N3—H3N···O4i	0.89 (2)	2.07 (2)	2.912 (2)	157 (2)
N4—H4N···N3	0.88 (2)	2.23 (2)	2.692 (2)	113 (2)
N4—H4N···Cl2	0.88 (2)	2.41 (2)	2.934 (2)	119 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.83 (3)	1.89 (3)	2.612 (2)	144 (3)
O3—H3O⋯O4i	0.83 (3)	2.33 (3)	2.854 (2)	122 (2)
O7—H7O⋯O8	0.89 (3)	1.81 (3)	2.607 (2)	147 (2)
O7—H7O⋯O8ii	0.89 (3)	2.46 (3)	2.964 (2)	116 (2)
N1—H1N⋯O8ii	0.87 (2)	2.06 (2)	2.911 (2)	164 (2)
N2—H2N⋯N1	0.82 (2)	2.24 (2)	2.700 (2)	116 (2)
N2—H2N⋯Cl1	0.82 (2)	2.47 (2)	2.930 (2)	116 (2)
N3—H3N⋯O4i	0.89 (2)	2.07 (2)	2.912 (2)	157 (2)
N4—H4N⋯N3	0.88 (2)	2.23 (2)	2.692 (2)	113 (2)
N4—H4N⋯Cl2	0.88 (2)	2.41 (2)	2.934 (2)	119 (2)

Symmetry codes: (i) ; (ii) .