3-[4-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zin-2-yl)phen-yl]-2-hy-droxy-1-mesitylprop-2-en-1-one hexane hemisolvate.

In the title compound, C(29)H(27)N(3)O(4)S·0.5C(6)H(14), the heterocyclic thia-zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.500 (5) and 0.229 (5) Å, respectively, on opposite sides from the mean plane formed by the remaining ring atoms. The mean planes of the pyrazole ring and the benzene ring bonded to it form a dihedral angle of 35.76 (11)° and an intra-molecular O-H⋯O hydrogen bond ocurs. The crystal structure features O-H⋯O and C-H⋯O hydrogen bonds. There is a half-mol-ecule of hexane in the asymmetric unit lying about an inversion center. It is disordered over two sets of sites with occupancy factors 0.590 (9) and 0.410 (9).

Related literature

For the synthesis and biological activity of benzothia­zine derivatives, see: Ahmad et al. (2010 ▶); Siddiqui et al. (2007 ▶). For related structures, see: Siddiqui et al. (2008 ▶); Bukhari et al. (2008 ▶). For the preparation of the chalcone, see: Furniss et al. (1989 ▶).

Experimental

Crystal data

C29H27N3O4S·0.5C6H14

M = 556.68

Monoclinic,

a = 7.1772 (2) Å

b = 23.2178 (5) Å

c = 16.7740 (4) Å

β = 99.526 (1)°

V = 2756.65 (12) Å3

Z = 4

Cu Kα radiation

μ = 1.39 mm−1

T = 173 K

0.20 × 0.05 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.768, T max = 0.946

28059 measured reflections

4979 independent reflections

4190 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.158

S = 1.04

4979 reflections

377 parameters

10 restraints

H-atom parameters constrained

Δρmax = 1.21 e Å−3

Δρmin = −0.66 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000712/fj2493sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000712/fj2493Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000712/fj2493Isup3.cml

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

C29H27N3O4S·0.5C6H14	F(000) = 1180
Mr = 556.68	Dx = 1.341 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 6317 reflections
a = 7.1772 (2) Å	θ = 3.3–68.1°
b = 23.2178 (5) Å	µ = 1.39 mm−1
c = 16.7740 (4) Å	T = 173 K
β = 99.526 (1)°	Needle, yellow
V = 2756.65 (12) Å3	0.20 × 0.05 × 0.04 mm
Z = 4

Bruker APEXII CCD diffractometer	4979 independent reflections
Radiation source: fine-focus sealed tube	4190 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω and φ scans	θmax = 68.1°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.768, Tmax = 0.946	k = −27→26
28059 measured reflections	l = −17→20

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0769P)2 + 4.2798P] where P = (Fo2 + 2Fc2)/3
4979 reflections	(Δ/σ)max = 0.003
377 parameters	Δρmax = 1.21 e Å−3
10 restraints	Δρmin = −0.66 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	Occ. (<1)
S1	1.13474 (10)	0.58533 (3)	0.20982 (4)	0.02532 (19)
O1	1.0238 (3)	0.62094 (8)	0.25325 (12)	0.0302 (5)
O2	1.1891 (3)	0.60647 (8)	0.13687 (12)	0.0332 (5)
O3	0.4765 (3)	0.20587 (8)	0.44658 (11)	0.0285 (4)
H3O	0.4255	0.1733	0.4458	0.043*
O4	0.3515 (3)	0.14501 (8)	0.56022 (13)	0.0350 (5)
N1	1.0174 (3)	0.52495 (10)	0.18792 (13)	0.0285 (5)
N2	1.0892 (3)	0.45865 (9)	0.38601 (13)	0.0222 (5)
N3	0.9178 (3)	0.43723 (9)	0.35111 (13)	0.0217 (5)
C1	1.3383 (4)	0.56538 (11)	0.27865 (16)	0.0252 (6)
C2	1.5067 (4)	0.59522 (12)	0.27961 (18)	0.0304 (6)
H2	1.5181	0.6231	0.2392	0.037*
C3	1.6571 (4)	0.58368 (12)	0.34021 (19)	0.0327 (7)
H3	1.7718	0.6045	0.3424	0.039*
C4	1.6416 (4)	0.54185 (12)	0.39796 (18)	0.0295 (6)
H4	1.7452	0.5346	0.4399	0.035*
C5	1.4761 (4)	0.51059 (11)	0.39475 (17)	0.0251 (6)
H5	1.4689	0.4809	0.4330	0.030*
C6	1.3202 (4)	0.52247 (11)	0.33576 (16)	0.0225 (5)
C7	1.1412 (4)	0.49174 (11)	0.32872 (16)	0.0221 (5)
C8	1.0034 (4)	0.49272 (11)	0.25929 (16)	0.0240 (6)
C9	1.0698 (7)	0.49052 (15)	0.1201 (2)	0.0551 (11)
H9A	0.9775	0.4595	0.1059	0.083*
H9B	1.1957	0.4738	0.1366	0.083*
H9C	1.0706	0.5155	0.0730	0.083*
C10	0.8590 (4)	0.45768 (11)	0.27444 (16)	0.0239 (6)
C11	0.6749 (4)	0.44530 (13)	0.22205 (17)	0.0313 (6)
H11A	0.6405	0.4776	0.1849	0.047*
H11B	0.5771	0.4401	0.2558	0.047*
H11C	0.6859	0.4101	0.1909	0.047*
C12	0.8229 (3)	0.39903 (11)	0.39740 (16)	0.0210 (5)
C13	0.8406 (4)	0.40655 (11)	0.48052 (16)	0.0230 (6)
H13	0.9112	0.4380	0.5062	0.028*
C14	0.7546 (4)	0.36800 (11)	0.52546 (16)	0.0224 (5)
H14	0.7668	0.3733	0.5822	0.027*
C15	0.6494 (3)	0.32111 (11)	0.48915 (16)	0.0211 (5)
C16	0.6317 (4)	0.31543 (11)	0.40510 (16)	0.0232 (5)
H16	0.5587	0.2847	0.3788	0.028*
C17	0.7180 (4)	0.35349 (11)	0.35994 (16)	0.0227 (5)
H17	0.7057	0.3486	0.3031	0.027*
C18	0.5692 (4)	0.28073 (11)	0.54079 (16)	0.0226 (5)
H18	0.5722	0.2927	0.5952	0.027*
C19	0.4912 (4)	0.22864 (11)	0.52148 (16)	0.0238 (6)
C20	0.4184 (4)	0.19208 (11)	0.58181 (17)	0.0252 (6)
C21	0.4307 (4)	0.21365 (11)	0.66674 (16)	0.0251 (6)
C22	0.2874 (4)	0.24899 (11)	0.68694 (16)	0.0252 (6)
C23	0.3056 (4)	0.27042 (12)	0.76527 (17)	0.0282 (6)
H23	0.2093	0.2946	0.7794	0.034*
C24	0.4618 (4)	0.25727 (13)	0.82337 (17)	0.0331 (7)
C25	0.5993 (4)	0.22111 (14)	0.80197 (18)	0.0356 (7)
H25	0.7050	0.2113	0.8416	0.043*
C26	0.5871 (4)	0.19889 (13)	0.72447 (18)	0.0309 (6)
C27	0.1172 (4)	0.26465 (13)	0.62553 (17)	0.0314 (6)
H27A	0.0241	0.2843	0.6526	0.047*
H27B	0.0611	0.2296	0.5993	0.047*
H27C	0.1556	0.2903	0.5848	0.047*
C28	0.4801 (5)	0.28102 (17)	0.90764 (19)	0.0476 (9)
H28A	0.5311	0.2512	0.9466	0.071*
H28B	0.3556	0.2931	0.9181	0.071*
H28C	0.5656	0.3142	0.9131	0.072*
C29	0.7408 (4)	0.16001 (15)	0.7048 (2)	0.0438 (8)
H29A	0.7206	0.1209	0.7235	0.066*
H29B	0.8637	0.1742	0.7318	0.066*
H29C	0.7382	0.1596	0.6462	0.066*
C31	0.803 (3)	0.1081 (5)	0.5070 (14)	0.217 (9)	0.590 (10)
H31A	0.7757	0.1441	0.4766	0.326*	0.590 (10)
H31B	0.8510	0.1170	0.5637	0.326*	0.590 (10)
H31C	0.6864	0.0854	0.5034	0.326*	0.590 (10)
C32	0.948 (3)	0.0742 (4)	0.4719 (11)	0.133 (5)	0.590 (10)
H32A	1.0731	0.0932	0.4809	0.159*	0.590 (10)
H32B	0.9081	0.0664	0.4135	0.159*	0.590 (10)
C33	0.9451 (14)	0.0198 (3)	0.5233 (6)	0.122 (5)	0.590 (10)
H33A	1.0099	0.0257	0.5795	0.146*	0.590 (10)
H33B	0.8150	0.0057	0.5235	0.146*	0.590 (10)
C34	0.955 (5)	0.0886 (9)	0.5440 (16)	0.217 (9)	0.410 (10)
H34A	0.9759	0.1303	0.5444	0.326*	0.410 (10)
H34B	1.0703	0.0691	0.5695	0.326*	0.410 (10)
H34C	0.8520	0.0798	0.5740	0.326*	0.410 (10)
C35	0.902 (4)	0.0682 (7)	0.4580 (14)	0.133 (5)	0.410 (10)
H35A	0.7733	0.0811	0.4337	0.159*	0.410 (10)
H35B	0.9935	0.0814	0.4239	0.159*	0.410 (10)
C36	0.9098 (19)	0.0039 (6)	0.4696 (12)	0.122 (5)	0.410 (10)
H36A	0.9175	−0.0162	0.4183	0.146*	0.410 (10)
H36B	0.7983	−0.0103	0.4914	0.146*	0.410 (10)

	U11	U22	U33	U12	U13	U23
S1	0.0326 (4)	0.0185 (3)	0.0261 (4)	0.0007 (3)	0.0084 (3)	0.0052 (2)
O1	0.0337 (11)	0.0220 (10)	0.0367 (11)	0.0032 (8)	0.0109 (9)	0.0033 (8)
O2	0.0439 (12)	0.0270 (10)	0.0306 (11)	0.0030 (9)	0.0117 (9)	0.0109 (8)
O3	0.0361 (11)	0.0214 (10)	0.0290 (10)	−0.0087 (8)	0.0085 (8)	−0.0041 (8)
O4	0.0454 (12)	0.0229 (10)	0.0378 (12)	−0.0097 (9)	0.0099 (9)	−0.0008 (9)
N1	0.0407 (14)	0.0235 (12)	0.0218 (12)	−0.0029 (10)	0.0063 (10)	0.0045 (9)
N2	0.0236 (11)	0.0187 (11)	0.0242 (11)	−0.0022 (9)	0.0040 (9)	0.0012 (9)
N3	0.0249 (11)	0.0178 (10)	0.0221 (11)	−0.0026 (9)	0.0032 (9)	0.0010 (9)
C1	0.0306 (14)	0.0206 (13)	0.0259 (14)	0.0011 (11)	0.0094 (11)	0.0004 (11)
C2	0.0372 (16)	0.0221 (14)	0.0356 (16)	−0.0010 (12)	0.0165 (13)	0.0046 (12)
C3	0.0288 (15)	0.0274 (15)	0.0444 (18)	−0.0036 (12)	0.0131 (13)	0.0001 (13)
C4	0.0246 (14)	0.0283 (14)	0.0362 (16)	0.0001 (11)	0.0064 (12)	−0.0003 (12)
C5	0.0286 (14)	0.0206 (13)	0.0277 (14)	0.0001 (11)	0.0087 (11)	0.0019 (11)
C6	0.0269 (13)	0.0180 (12)	0.0242 (13)	−0.0004 (10)	0.0094 (11)	−0.0013 (10)
C7	0.0279 (14)	0.0162 (12)	0.0231 (13)	0.0007 (10)	0.0065 (11)	0.0007 (10)
C8	0.0309 (14)	0.0203 (13)	0.0210 (13)	0.0009 (11)	0.0052 (11)	0.0023 (10)
C9	0.108 (3)	0.0327 (18)	0.0291 (17)	−0.0122 (19)	0.0229 (19)	−0.0026 (14)
C10	0.0293 (14)	0.0186 (13)	0.0230 (13)	0.0007 (10)	0.0019 (11)	−0.0001 (10)
C11	0.0332 (15)	0.0283 (15)	0.0291 (15)	−0.0037 (12)	−0.0040 (12)	0.0033 (12)
C12	0.0208 (12)	0.0171 (12)	0.0254 (13)	0.0019 (10)	0.0045 (10)	0.0022 (10)
C13	0.0244 (13)	0.0172 (12)	0.0265 (14)	−0.0024 (10)	0.0018 (11)	−0.0016 (10)
C14	0.0270 (13)	0.0196 (12)	0.0205 (13)	0.0015 (10)	0.0035 (10)	0.0009 (10)
C15	0.0201 (12)	0.0192 (12)	0.0247 (13)	0.0013 (10)	0.0053 (10)	0.0002 (10)
C16	0.0234 (13)	0.0192 (12)	0.0270 (14)	−0.0026 (10)	0.0045 (11)	−0.0034 (11)
C17	0.0259 (13)	0.0196 (13)	0.0230 (13)	0.0013 (10)	0.0053 (10)	−0.0004 (10)
C18	0.0228 (13)	0.0229 (13)	0.0226 (13)	0.0005 (10)	0.0049 (10)	0.0004 (10)
C19	0.0231 (13)	0.0224 (13)	0.0259 (14)	0.0004 (10)	0.0042 (11)	−0.0001 (11)
C20	0.0220 (13)	0.0195 (13)	0.0335 (15)	0.0004 (10)	0.0035 (11)	0.0040 (11)
C21	0.0282 (14)	0.0192 (13)	0.0281 (14)	−0.0061 (11)	0.0052 (11)	0.0050 (11)
C22	0.0306 (14)	0.0200 (13)	0.0250 (14)	−0.0049 (11)	0.0049 (11)	0.0048 (11)
C23	0.0337 (15)	0.0252 (14)	0.0270 (14)	−0.0070 (12)	0.0087 (12)	0.0036 (11)
C24	0.0368 (16)	0.0372 (16)	0.0257 (15)	−0.0151 (13)	0.0067 (12)	0.0046 (12)
C25	0.0275 (15)	0.0454 (18)	0.0314 (16)	−0.0085 (13)	−0.0029 (12)	0.0106 (14)
C26	0.0239 (14)	0.0307 (15)	0.0371 (16)	−0.0047 (11)	0.0019 (12)	0.0088 (12)
C27	0.0334 (15)	0.0327 (15)	0.0270 (15)	0.0053 (12)	0.0014 (12)	0.0030 (12)
C28	0.050 (2)	0.064 (2)	0.0285 (17)	−0.0206 (18)	0.0037 (14)	−0.0018 (16)
C29	0.0319 (16)	0.0445 (19)	0.053 (2)	0.0068 (14)	0.0022 (15)	0.0049 (16)
C31	0.20 (2)	0.205 (18)	0.25 (2)	−0.049 (16)	0.053 (18)	0.100 (15)
C32	0.131 (11)	0.098 (5)	0.191 (11)	−0.030 (6)	0.092 (9)	−0.036 (7)
C33	0.078 (6)	0.076 (7)	0.196 (14)	−0.039 (5)	−0.021 (8)	0.007 (7)
C34	0.20 (2)	0.205 (18)	0.25 (2)	−0.049 (16)	0.053 (18)	0.100 (15)
C35	0.131 (11)	0.098 (5)	0.191 (11)	−0.030 (6)	0.092 (9)	−0.036 (7)
C36	0.078 (6)	0.076 (7)	0.196 (14)	−0.039 (5)	−0.021 (8)	0.007 (7)

S1—O1	1.428 (2)	C18—C19	1.349 (4)
S1—O2	1.431 (2)	C18—H18	0.9500
S1—N1	1.645 (2)	C19—C20	1.481 (4)
S1—C1	1.767 (3)	C20—C21	1.499 (4)
O3—C19	1.351 (3)	C21—C26	1.398 (4)
O3—H3O	0.8400	C21—C22	1.401 (4)
O4—C20	1.224 (3)	C22—C23	1.391 (4)
N1—C8	1.429 (3)	C22—C27	1.506 (4)
N1—C9	1.489 (4)	C23—C24	1.392 (4)
N2—C7	1.331 (3)	C23—H23	0.9500
N2—N3	1.366 (3)	C24—C25	1.387 (5)
N3—C10	1.370 (3)	C24—C28	1.503 (4)
N3—C12	1.424 (3)	C25—C26	1.388 (4)
C1—C2	1.391 (4)	C25—H25	0.9500
C1—C6	1.403 (4)	C26—C29	1.504 (4)
C2—C3	1.381 (4)	C27—H27A	0.9800
C2—H2	0.9500	C27—H27B	0.9800
C3—C4	1.389 (4)	C27—H27C	0.9800
C3—H3	0.9500	C28—H28A	0.9800
C4—C5	1.386 (4)	C28—H28B	0.9800
C4—H4	0.9500	C28—H28C	0.9800
C5—C6	1.393 (4)	C29—H29A	0.9800
C5—H5	0.9500	C29—H29B	0.9800
C6—C7	1.457 (4)	C29—H29C	0.9800
C7—C8	1.398 (4)	C31—C32	1.502 (10)
C8—C10	1.374 (4)	C31—H31A	0.9800
C9—H9A	0.9800	C31—H31B	0.9800
C9—H9B	0.9800	C31—H31C	0.9800
C9—H9C	0.9800	C32—C33	1.531 (9)
C10—C11	1.489 (4)	C32—H32A	0.9900
C11—H11A	0.9800	C32—H32B	0.9900
C11—H11B	0.9800	C33—C33i	1.509 (10)
C11—H11C	0.9800	C33—H33A	0.9900
C12—C17	1.387 (4)	C33—H33B	0.9900
C12—C13	1.390 (4)	C34—C35	1.507 (10)
C13—C14	1.380 (4)	C34—H34A	0.9800
C13—H13	0.9500	C34—H34B	0.9800
C14—C15	1.405 (4)	C34—H34C	0.9800
C14—H14	0.9500	C35—C36	1.504 (10)
C15—C16	1.401 (4)	C35—H35A	0.9900
C15—C18	1.458 (4)	C35—H35B	0.9900
C16—C17	1.376 (4)	C36—C36i	1.520 (10)
C16—H16	0.9500	C36—H36A	0.9900
C17—H17	0.9500	C36—H36B	0.9900
O1—S1—O2	119.43 (12)	O3—C19—C20	115.4 (2)
O1—S1—N1	107.41 (12)	O4—C20—C19	118.4 (3)
O2—S1—N1	107.64 (12)	O4—C20—C21	122.5 (2)
O1—S1—C1	106.79 (12)	C19—C20—C21	119.1 (2)
O2—S1—C1	109.62 (13)	C26—C21—C22	120.9 (3)
N1—S1—C1	105.05 (12)	C26—C21—C20	119.4 (3)
C19—O3—H3O	109.5	C22—C21—C20	119.7 (2)
C8—N1—C9	114.9 (2)	C23—C22—C21	118.7 (3)
C8—N1—S1	111.31 (18)	C23—C22—C27	119.9 (3)
C9—N1—S1	116.3 (2)	C21—C22—C27	121.4 (2)
C7—N2—N3	103.9 (2)	C22—C23—C24	121.4 (3)
N2—N3—C10	113.1 (2)	C22—C23—H23	119.3
N2—N3—C12	118.1 (2)	C24—C23—H23	119.3
C10—N3—C12	128.8 (2)	C25—C24—C23	118.5 (3)
C2—C1—C6	121.6 (3)	C25—C24—C28	120.7 (3)
C2—C1—S1	120.0 (2)	C23—C24—C28	120.9 (3)
C6—C1—S1	118.2 (2)	C24—C25—C26	122.0 (3)
C3—C2—C1	118.9 (3)	C24—C25—H25	119.0
C3—C2—H2	120.5	C26—C25—H25	119.0
C1—C2—H2	120.5	C25—C26—C21	118.5 (3)
C2—C3—C4	120.4 (3)	C25—C26—C29	119.6 (3)
C2—C3—H3	119.8	C21—C26—C29	121.9 (3)
C4—C3—H3	119.8	C22—C27—H27A	109.5
C5—C4—C3	120.4 (3)	C22—C27—H27B	109.5
C5—C4—H4	119.8	H27A—C27—H27B	109.5
C3—C4—H4	119.8	C22—C27—H27C	109.5
C4—C5—C6	120.4 (3)	H27A—C27—H27C	109.5
C4—C5—H5	119.8	H27B—C27—H27C	109.5
C6—C5—H5	119.8	C24—C28—H28A	109.5
C5—C6—C1	118.1 (2)	C24—C28—H28B	109.5
C5—C6—C7	123.7 (2)	H28A—C28—H28B	109.5
C1—C6—C7	118.2 (2)	C24—C28—H28C	109.5
N2—C7—C8	111.5 (2)	H28A—C28—H28C	109.5
N2—C7—C6	125.0 (2)	H28B—C28—H28C	109.5
C8—C7—C6	123.5 (2)	C26—C29—H29A	109.5
C10—C8—C7	106.7 (2)	C26—C29—H29B	109.5
C10—C8—N1	128.7 (2)	H29A—C29—H29B	109.5
C7—C8—N1	124.6 (2)	C26—C29—H29C	109.5
N1—C9—H9A	109.5	H29A—C29—H29C	109.5
N1—C9—H9B	109.5	H29B—C29—H29C	109.5
H9A—C9—H9B	109.5	C32—C31—H31A	109.5
N1—C9—H9C	109.5	C32—C31—H31B	109.5
H9A—C9—H9C	109.5	H31A—C31—H31B	109.5
H9B—C9—H9C	109.5	C32—C31—H31C	109.5
N3—C10—C8	104.7 (2)	H31A—C31—H31C	109.5
N3—C10—C11	126.3 (2)	H31B—C31—H31C	109.5
C8—C10—C11	128.9 (2)	C31—C32—C33	97.9 (8)
C10—C11—H11A	109.5	C31—C32—H32A	112.2
C10—C11—H11B	109.5	C33—C32—H32A	112.2
H11A—C11—H11B	109.5	C31—C32—H32B	112.2
C10—C11—H11C	109.5	C33—C32—H32B	112.2
H11A—C11—H11C	109.5	H32A—C32—H32B	109.8
H11B—C11—H11C	109.5	C33i—C33—C32	98.9 (8)
C17—C12—C13	120.2 (2)	C33i—C33—H33A	112.0
C17—C12—N3	120.0 (2)	C32—C33—H33A	112.0
C13—C12—N3	119.7 (2)	C33i—C33—H33B	112.0
C14—C13—C12	119.4 (2)	C32—C33—H33B	112.0
C14—C13—H13	120.3	H33A—C33—H33B	109.7
C12—C13—H13	120.3	C35—C34—H34A	109.5
C13—C14—C15	121.5 (2)	C35—C34—H34B	109.5
C13—C14—H14	119.2	H34A—C34—H34B	109.5
C15—C14—H14	119.2	C35—C34—H34C	109.5
C16—C15—C14	117.5 (2)	H34A—C34—H34C	109.5
C16—C15—C18	123.9 (2)	H34B—C34—H34C	109.5
C14—C15—C18	118.5 (2)	C36—C35—C34	101.0 (8)
C17—C16—C15	121.3 (2)	C36—C35—H35A	111.6
C17—C16—H16	119.4	C34—C35—H35A	111.6
C15—C16—H16	119.4	C36—C35—H35B	111.6
C16—C17—C12	120.0 (2)	C34—C35—H35B	111.6
C16—C17—H17	120.0	H35A—C35—H35B	109.4
C12—C17—H17	120.0	C35—C36—C36i	102.5 (8)
C19—C18—C15	128.5 (2)	C35—C36—H36A	111.3
C19—C18—H18	115.7	C36i—C36—H36A	111.3
C15—C18—H18	115.7	C35—C36—H36B	111.3
C18—C19—O3	122.6 (2)	C36i—C36—H36B	111.3
C18—C19—C20	121.9 (2)	H36A—C36—H36B	109.2
O1—S1—N1—C8	−66.4 (2)	N1—C8—C10—C11	−2.4 (5)
O2—S1—N1—C8	163.78 (18)	N2—N3—C12—C17	−144.2 (2)
C1—S1—N1—C8	47.0 (2)	C10—N3—C12—C17	37.6 (4)
O1—S1—N1—C9	159.4 (2)	N2—N3—C12—C13	33.9 (3)
O2—S1—N1—C9	29.6 (3)	C10—N3—C12—C13	−144.3 (3)
C1—S1—N1—C9	−87.2 (3)	C17—C12—C13—C14	0.7 (4)
C7—N2—N3—C10	−2.0 (3)	N3—C12—C13—C14	−177.4 (2)
C7—N2—N3—C12	179.5 (2)	C12—C13—C14—C15	0.1 (4)
O1—S1—C1—C2	−98.2 (2)	C13—C14—C15—C16	−1.2 (4)
O2—S1—C1—C2	32.5 (3)	C13—C14—C15—C18	177.4 (2)
N1—S1—C1—C2	147.9 (2)	C14—C15—C16—C17	1.6 (4)
O1—S1—C1—C6	76.6 (2)	C18—C15—C16—C17	−177.0 (2)
O2—S1—C1—C6	−152.7 (2)	C15—C16—C17—C12	−0.9 (4)
N1—S1—C1—C6	−37.3 (2)	C13—C12—C17—C16	−0.3 (4)
C6—C1—C2—C3	−2.5 (4)	N3—C12—C17—C16	177.8 (2)
S1—C1—C2—C3	172.1 (2)	C16—C15—C18—C19	10.3 (4)
C1—C2—C3—C4	1.7 (4)	C14—C15—C18—C19	−168.2 (3)
C2—C3—C4—C5	1.0 (4)	C15—C18—C19—O3	−0.1 (4)
C3—C4—C5—C6	−2.9 (4)	C15—C18—C19—C20	178.9 (2)
C4—C5—C6—C1	2.1 (4)	C18—C19—C20—O4	−179.2 (3)
C4—C5—C6—C7	−179.7 (2)	O3—C19—C20—O4	−0.1 (4)
C2—C1—C6—C5	0.6 (4)	C18—C19—C20—C21	0.3 (4)
S1—C1—C6—C5	−174.1 (2)	O3—C19—C20—C21	179.4 (2)
C2—C1—C6—C7	−177.7 (2)	O4—C20—C21—C26	86.3 (3)
S1—C1—C6—C7	7.6 (3)	C19—C20—C21—C26	−93.1 (3)
N3—N2—C7—C8	1.6 (3)	O4—C20—C21—C22	−94.7 (3)
N3—N2—C7—C6	−177.3 (2)	C19—C20—C21—C22	85.9 (3)
C5—C6—C7—N2	15.8 (4)	C26—C21—C22—C23	1.6 (4)
C1—C6—C7—N2	−166.0 (2)	C20—C21—C22—C23	−177.4 (2)
C5—C6—C7—C8	−162.9 (3)	C26—C21—C22—C27	−179.3 (2)
C1—C6—C7—C8	15.3 (4)	C20—C21—C22—C27	1.7 (4)
N2—C7—C8—C10	−0.7 (3)	C21—C22—C23—C24	−0.3 (4)
C6—C7—C8—C10	178.2 (2)	C27—C22—C23—C24	−179.4 (3)
N2—C7—C8—N1	179.2 (2)	C22—C23—C24—C25	−1.1 (4)
C6—C7—C8—N1	−1.9 (4)	C22—C23—C24—C28	179.6 (3)
C9—N1—C8—C10	−78.1 (4)	C23—C24—C25—C26	1.3 (4)
S1—N1—C8—C10	147.0 (2)	C28—C24—C25—C26	−179.5 (3)
C9—N1—C8—C7	102.0 (3)	C24—C25—C26—C21	−0.1 (4)
S1—N1—C8—C7	−32.9 (3)	C24—C25—C26—C29	179.8 (3)
N2—N3—C10—C8	1.6 (3)	C22—C21—C26—C25	−1.4 (4)
C12—N3—C10—C8	180.0 (2)	C20—C21—C26—C25	177.6 (2)
N2—N3—C10—C11	−176.4 (2)	C22—C21—C26—C29	178.7 (3)
C12—N3—C10—C11	1.9 (4)	C20—C21—C26—C29	−2.4 (4)
C7—C8—C10—N3	−0.6 (3)	C31—C32—C33—C33i	167.7 (17)
N1—C8—C10—N3	179.6 (3)	C34—C35—C36—C36i	−43 (3)
C7—C8—C10—C11	177.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2ii	0.84	2.15	2.854 (3)	141.
O3—H3O···O4	0.84	2.18	2.646 (3)	115.
C3—H3···O1iii	0.95	2.56	3.328 (3)	138.
C23—H23···O1iv	0.95	2.58	3.436 (4)	150.
C9—H9C···O2	0.98	2.46	2.825 (4)	102.
C16—H16···O3	0.95	2.28	2.907 (3)	123.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2i	0.84	2.15	2.854 (3)	141
O3—H3O⋯O4	0.84	2.18	2.646 (3)	115
C3—H3⋯O1ii	0.95	2.56	3.328 (3)	138
C23—H23⋯O1iii	0.95	2.58	3.436 (4)	150
C16—H16⋯O3	0.95	2.28	2.907 (3)	123

Symmetry codes: (i) ; (ii) ; (iii) .