2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zin-2-yl)-N-(3-meth-oxy-benz-yl)acetamide.

The asymmetric unit of the title compound, C(21)H(22)N(4)O(4)S, contains two mol-ecules (A and B), in which the thia-zine rings adopt an S-envelope conformation with the S atoms displaced by 0.621 (2) and 0.697 (2) Å from the mean planes formed by the remaining ring atoms. The dihedral angles between the N-methyl-acetamide groups and the meth-oxy-benzene rings are 8.67 (10) and 54.49 (6)° in the two mol-ecules and the equivalent torsion angles in the N-methyl-acetamide chains connecting the ring systems also differ. In the crystal, N-H⋯O hydrogen bonds connect the components into C(4) [100] chains of alternating A and B mol-ecules. The packing is consolidated by weak C-H⋯O inter-actions, which generate a three-dimensional network.

Related literature

For therapeutic applications of benzothia­zines, see: Turck et al. (1996) ▶; Lombardino et al. (1973 ▶); Zinnes et al. (1973 ▶). For therapeutic applications of pyrrazoles, see: Silverstein et al. (2000 ▶). For the properties and crystal structures of related pyrazolo­benzothia­zine derivatives, see: Ahmad et al. (2010a ▶,b ▶, 2012 ▶; 2011a ▶,b ▶).

Experimental

Crystal data

C21H22N4O4S

M = 426.49

Monoclinic,

a = 8.6541 (1) Å

b = 25.8809 (3) Å

c = 18.3892 (2) Å

β = 92.208 (1)°

V = 4115.68 (8) Å3

Z = 8

Cu Kα radiation

μ = 1.71 mm−1

T = 173 K

0.14 × 0.12 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.796, T max = 0.967

70993 measured reflections

7975 independent reflections

6621 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.02

7975 reflections

547 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.37 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040226/hb6961sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040226/hb6961Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812040226/hb6961Isup3.cml

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

C21H22N4O4S	F(000) = 1792
Mr = 426.49	Dx = 1.377 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9915 reflections
a = 8.6541 (1) Å	θ = 3.4–71.7°
b = 25.8809 (3) Å	µ = 1.71 mm−1
c = 18.3892 (2) Å	T = 173 K
β = 92.208 (1)°	Plate, colorless
V = 4115.68 (8) Å3	0.14 × 0.12 × 0.02 mm
Z = 8

Bruker APEXII CCD diffractometer	7975 independent reflections
Radiation source: fine-focus sealed tube	6621 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω and φ scans	θmax = 72.7°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.796, Tmax = 0.967	k = −31→32
70993 measured reflections	l = −22→22

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0486P)2 + 1.780P] where P = (Fo2 + 2Fc2)/3
7975 reflections	(Δ/σ)max = 0.001
547 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.37 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
S1	0.73006 (5)	0.718057 (16)	0.68662 (2)	0.03077 (11)
O1	0.73608 (18)	0.75309 (5)	0.74693 (7)	0.0448 (3)
O2	0.58770 (14)	0.69282 (5)	0.66768 (8)	0.0427 (3)
O3	0.66878 (13)	0.64371 (5)	0.36992 (6)	0.0305 (3)
O4	1.13937 (15)	0.51550 (5)	0.09408 (7)	0.0442 (3)
N1	0.78516 (16)	0.74988 (5)	0.61494 (7)	0.0283 (3)
N2	0.94469 (15)	0.64777 (5)	0.50587 (7)	0.0268 (3)
N3	0.90464 (15)	0.68467 (5)	0.45640 (7)	0.0258 (3)
N4	0.83869 (15)	0.61454 (5)	0.28889 (7)	0.0257 (3)
H4N	0.9357	0.6140	0.2762	0.031*
C1	0.86939 (19)	0.66886 (6)	0.70074 (9)	0.0277 (3)
C2	0.9089 (2)	0.65336 (7)	0.77123 (10)	0.0379 (4)
H2	0.8681	0.6709	0.8116	0.045*
C3	1.0082 (2)	0.61207 (8)	0.78196 (11)	0.0439 (5)
H3	1.0366	0.6012	0.8300	0.053*
C4	1.0666 (2)	0.58638 (7)	0.72289 (11)	0.0398 (4)
H4	1.1326	0.5574	0.7308	0.048*
C5	1.02988 (19)	0.60238 (6)	0.65256 (10)	0.0310 (4)
H5	1.0717	0.5847	0.6126	0.037*
C6	0.93145 (18)	0.64456 (6)	0.64015 (9)	0.0252 (3)
C7	0.90162 (17)	0.66776 (6)	0.56918 (8)	0.0238 (3)
C8	0.83336 (18)	0.71665 (6)	0.55833 (8)	0.0242 (3)
C9	0.83390 (18)	0.72636 (6)	0.48488 (8)	0.0247 (3)
C10	0.7748 (2)	0.77070 (7)	0.44095 (9)	0.0324 (4)
H10A	0.7004	0.7902	0.4689	0.039*
H10B	0.7238	0.7579	0.3960	0.039*
H10C	0.8612	0.7932	0.4289	0.039*
C11	0.8664 (2)	0.79951 (7)	0.62507 (10)	0.0343 (4)
H11A	0.8964	0.8127	0.5777	0.041*
H11B	0.9590	0.7944	0.6566	0.041*
H11C	0.7977	0.8244	0.6477	0.041*
C12	0.93011 (19)	0.67463 (7)	0.38043 (8)	0.0288 (3)
H12A	1.0292	0.6560	0.3760	0.035*
H12B	0.9377	0.7078	0.3541	0.035*
C13	0.79951 (18)	0.64258 (6)	0.34597 (8)	0.0237 (3)
C14	0.72376 (19)	0.58481 (7)	0.24711 (9)	0.0303 (4)
H14A	0.6516	0.6091	0.2218	0.036*
H14B	0.6632	0.5642	0.2813	0.036*
C15	0.78873 (19)	0.54888 (6)	0.19144 (8)	0.0260 (3)
C16	0.94083 (19)	0.55117 (6)	0.16971 (9)	0.0290 (3)
H16	1.0103	0.5759	0.1909	0.035*
C17	0.9909 (2)	0.51720 (7)	0.11689 (9)	0.0315 (4)
C18	0.8897 (2)	0.48220 (7)	0.08388 (9)	0.0350 (4)
H18	0.9240	0.4596	0.0471	0.042*
C19	0.7390 (2)	0.48049 (7)	0.10484 (10)	0.0381 (4)
H19	0.6688	0.4567	0.0821	0.046*
C20	0.6881 (2)	0.51308 (7)	0.15891 (10)	0.0339 (4)
H20	0.5844	0.5109	0.1737	0.041*
C21	1.2412 (2)	0.55582 (9)	0.11614 (13)	0.0518 (5)
H21A	1.3392	0.5519	0.0917	0.062*
H21B	1.2605	0.5542	0.1690	0.062*
H21C	1.1945	0.5892	0.1030	0.062*
S2	0.75867 (5)	0.300172 (18)	1.06466 (2)	0.03455 (11)
O5	0.77325 (18)	0.27220 (6)	1.13161 (7)	0.0496 (4)
O6	0.88416 (15)	0.33157 (6)	1.04272 (7)	0.0425 (3)
O7	0.84261 (13)	0.35681 (5)	0.74617 (6)	0.0311 (3)
O8	0.25890 (16)	0.51780 (5)	0.54673 (8)	0.0489 (4)
N5	0.72180 (17)	0.25814 (6)	0.99927 (7)	0.0318 (3)
N6	0.54399 (15)	0.34265 (5)	0.86314 (7)	0.0248 (3)
N7	0.61082 (15)	0.30530 (5)	0.82299 (7)	0.0240 (3)
N8	0.64844 (16)	0.38308 (6)	0.66855 (8)	0.0308 (3)
H8N	0.5534	0.3765	0.6524	0.037*
C22	0.5931 (2)	0.34022 (7)	1.06449 (9)	0.0307 (4)
C23	0.5371 (2)	0.35857 (8)	1.12924 (10)	0.0404 (4)
H23	0.5812	0.3473	1.1746	0.048*
C24	0.4164 (2)	0.39335 (8)	1.12678 (11)	0.0457 (5)
H24	0.3766	0.4060	1.1708	0.055*
C25	0.3525 (2)	0.41003 (7)	1.06055 (11)	0.0411 (4)
H25	0.2717	0.4349	1.0595	0.049*
C26	0.4056 (2)	0.39074 (7)	0.99589 (10)	0.0328 (4)
H26	0.3599	0.4020	0.9508	0.039*
C27	0.52598 (19)	0.35489 (6)	0.99667 (9)	0.0273 (3)
C28	0.57863 (18)	0.32881 (6)	0.93188 (8)	0.0240 (3)
C29	0.66903 (18)	0.28375 (6)	0.93412 (9)	0.0256 (3)
C30	0.68912 (18)	0.26942 (6)	0.86324 (9)	0.0257 (3)
C31	0.7701 (2)	0.22448 (7)	0.83220 (10)	0.0354 (4)
H31A	0.8316	0.2071	0.8708	0.042*
H31B	0.8385	0.2364	0.7944	0.042*
H31C	0.6939	0.2003	0.8109	0.042*
C32	0.6376 (3)	0.21044 (7)	1.01727 (11)	0.0452 (5)
H32A	0.6335	0.1874	0.9749	0.054*
H32B	0.5322	0.2192	1.0305	0.054*
H32C	0.6912	0.1930	1.0583	0.054*
C33	0.60293 (19)	0.30988 (6)	0.74456 (8)	0.0257 (3)
H33A	0.4954	0.3177	0.7278	0.031*
H33B	0.6333	0.2767	0.7225	0.031*
C34	0.71003 (17)	0.35267 (6)	0.72004 (8)	0.0236 (3)
C35	0.7295 (2)	0.42690 (8)	0.63715 (11)	0.0396 (4)
H35A	0.7603	0.4179	0.5874	0.048*
H35B	0.8246	0.4343	0.6670	0.048*
C36	0.6281 (2)	0.47419 (7)	0.63410 (10)	0.0354 (4)
C37	0.4907 (2)	0.47291 (7)	0.59220 (9)	0.0326 (4)
H37	0.4611	0.4421	0.5672	0.039*
C38	0.3965 (2)	0.51621 (7)	0.58663 (10)	0.0387 (4)
C39	0.4419 (3)	0.56167 (8)	0.62194 (13)	0.0509 (5)
H39	0.3795	0.5918	0.6172	0.061*
C40	0.5767 (3)	0.56283 (8)	0.66352 (13)	0.0565 (6)
H40	0.6066	0.5938	0.6879	0.068*
C41	0.6705 (3)	0.51915 (9)	0.67061 (12)	0.0496 (5)
H41	0.7628	0.5202	0.7002	0.059*
C42	0.2039 (2)	0.47010 (9)	0.51694 (13)	0.0520 (5)
H42A	0.1065	0.4760	0.4893	0.062*
H42B	0.1867	0.4456	0.5565	0.062*
H42C	0.2807	0.4559	0.4846	0.062*

	U11	U22	U33	U12	U13	U23
S1	0.0327 (2)	0.0311 (2)	0.0291 (2)	0.00564 (16)	0.00925 (17)	−0.00061 (15)
O1	0.0658 (9)	0.0403 (7)	0.0290 (6)	0.0125 (7)	0.0132 (6)	−0.0043 (5)
O2	0.0280 (6)	0.0434 (8)	0.0573 (8)	0.0044 (6)	0.0111 (6)	0.0064 (6)
O3	0.0220 (6)	0.0431 (7)	0.0266 (6)	−0.0017 (5)	0.0033 (5)	−0.0041 (5)
O4	0.0383 (7)	0.0459 (8)	0.0493 (8)	−0.0035 (6)	0.0146 (6)	−0.0187 (6)
N1	0.0340 (8)	0.0260 (7)	0.0250 (7)	0.0039 (6)	0.0045 (6)	−0.0037 (5)
N2	0.0250 (7)	0.0284 (7)	0.0267 (7)	0.0026 (5)	−0.0011 (6)	−0.0039 (5)
N3	0.0229 (7)	0.0314 (7)	0.0229 (6)	0.0013 (5)	0.0001 (5)	−0.0040 (5)
N4	0.0201 (6)	0.0330 (7)	0.0242 (6)	−0.0010 (5)	0.0029 (5)	−0.0037 (5)
C1	0.0274 (8)	0.0274 (8)	0.0285 (8)	−0.0017 (6)	0.0026 (7)	0.0018 (6)
C2	0.0462 (11)	0.0396 (10)	0.0281 (9)	−0.0011 (8)	0.0040 (8)	0.0022 (7)
C3	0.0519 (12)	0.0451 (11)	0.0342 (10)	0.0007 (9)	−0.0046 (9)	0.0124 (8)
C4	0.0384 (10)	0.0344 (10)	0.0461 (11)	0.0049 (8)	−0.0058 (9)	0.0098 (8)
C5	0.0269 (8)	0.0289 (8)	0.0372 (9)	0.0005 (7)	0.0003 (7)	−0.0003 (7)
C6	0.0217 (7)	0.0251 (8)	0.0287 (8)	−0.0034 (6)	−0.0013 (6)	−0.0008 (6)
C7	0.0192 (7)	0.0260 (8)	0.0262 (8)	0.0000 (6)	−0.0009 (6)	−0.0041 (6)
C8	0.0220 (7)	0.0263 (8)	0.0243 (7)	0.0021 (6)	0.0001 (6)	−0.0032 (6)
C9	0.0199 (7)	0.0285 (8)	0.0256 (8)	0.0005 (6)	−0.0005 (6)	−0.0037 (6)
C10	0.0324 (9)	0.0363 (9)	0.0286 (8)	0.0050 (7)	0.0009 (7)	0.0023 (7)
C11	0.0415 (10)	0.0282 (8)	0.0332 (9)	−0.0004 (7)	0.0007 (8)	−0.0053 (7)
C12	0.0243 (8)	0.0378 (9)	0.0244 (8)	−0.0029 (7)	0.0034 (7)	−0.0061 (7)
C13	0.0214 (7)	0.0286 (8)	0.0209 (7)	0.0018 (6)	0.0001 (6)	0.0031 (6)
C14	0.0234 (8)	0.0382 (9)	0.0292 (8)	−0.0033 (7)	0.0004 (7)	−0.0069 (7)
C15	0.0283 (8)	0.0270 (8)	0.0225 (7)	0.0001 (6)	−0.0016 (7)	0.0009 (6)
C16	0.0288 (8)	0.0305 (8)	0.0277 (8)	−0.0035 (7)	0.0003 (7)	−0.0043 (6)
C17	0.0340 (9)	0.0322 (9)	0.0286 (8)	−0.0001 (7)	0.0048 (7)	−0.0016 (7)
C18	0.0464 (11)	0.0294 (9)	0.0293 (9)	−0.0002 (8)	0.0014 (8)	−0.0062 (7)
C19	0.0430 (10)	0.0327 (9)	0.0381 (10)	−0.0089 (8)	−0.0053 (8)	−0.0071 (7)
C20	0.0290 (9)	0.0364 (9)	0.0361 (9)	−0.0053 (7)	−0.0015 (8)	−0.0017 (7)
C21	0.0338 (10)	0.0597 (13)	0.0632 (14)	−0.0082 (9)	0.0192 (10)	−0.0177 (11)
S2	0.0328 (2)	0.0449 (3)	0.0257 (2)	−0.00011 (18)	−0.00307 (17)	0.00447 (17)
O5	0.0581 (9)	0.0620 (9)	0.0283 (7)	0.0026 (7)	−0.0064 (6)	0.0098 (6)
O6	0.0301 (7)	0.0562 (8)	0.0409 (7)	−0.0053 (6)	−0.0041 (6)	0.0006 (6)
O7	0.0211 (6)	0.0437 (7)	0.0284 (6)	−0.0027 (5)	0.0003 (5)	−0.0008 (5)
O8	0.0414 (8)	0.0413 (8)	0.0641 (9)	0.0124 (6)	0.0046 (7)	0.0058 (7)
N5	0.0333 (8)	0.0337 (8)	0.0283 (7)	0.0045 (6)	−0.0008 (6)	0.0066 (6)
N6	0.0235 (7)	0.0260 (7)	0.0252 (7)	0.0017 (5)	0.0032 (5)	−0.0012 (5)
N7	0.0223 (6)	0.0269 (7)	0.0230 (6)	0.0019 (5)	0.0027 (5)	−0.0013 (5)
N8	0.0217 (7)	0.0377 (8)	0.0327 (7)	−0.0052 (6)	−0.0018 (6)	0.0060 (6)
C22	0.0307 (9)	0.0338 (9)	0.0278 (8)	−0.0063 (7)	0.0047 (7)	−0.0002 (7)
C23	0.0463 (11)	0.0487 (11)	0.0267 (9)	−0.0112 (9)	0.0074 (8)	−0.0039 (8)
C24	0.0496 (12)	0.0515 (12)	0.0374 (10)	−0.0103 (10)	0.0204 (9)	−0.0148 (9)
C25	0.0376 (10)	0.0367 (10)	0.0501 (11)	−0.0014 (8)	0.0144 (9)	−0.0108 (8)
C26	0.0308 (9)	0.0309 (9)	0.0371 (9)	−0.0012 (7)	0.0066 (8)	−0.0020 (7)
C27	0.0267 (8)	0.0278 (8)	0.0278 (8)	−0.0052 (6)	0.0069 (7)	0.0001 (6)
C28	0.0213 (7)	0.0270 (8)	0.0239 (8)	−0.0017 (6)	0.0029 (6)	0.0018 (6)
C29	0.0225 (8)	0.0282 (8)	0.0262 (8)	0.0019 (6)	0.0006 (6)	0.0037 (6)
C30	0.0192 (7)	0.0272 (8)	0.0307 (8)	0.0012 (6)	0.0011 (6)	−0.0001 (6)
C31	0.0305 (9)	0.0364 (9)	0.0392 (9)	0.0102 (7)	−0.0003 (8)	−0.0047 (7)
C32	0.0568 (13)	0.0354 (10)	0.0434 (11)	−0.0003 (9)	0.0001 (10)	0.0115 (8)
C33	0.0247 (8)	0.0304 (8)	0.0219 (7)	−0.0012 (6)	−0.0003 (6)	−0.0024 (6)
C34	0.0206 (7)	0.0314 (8)	0.0191 (7)	0.0004 (6)	0.0036 (6)	−0.0055 (6)
C35	0.0276 (9)	0.0452 (11)	0.0460 (11)	−0.0052 (8)	0.0027 (8)	0.0148 (8)
C36	0.0342 (9)	0.0364 (9)	0.0361 (9)	−0.0084 (7)	0.0065 (8)	0.0056 (7)
C37	0.0343 (9)	0.0298 (9)	0.0343 (9)	−0.0024 (7)	0.0076 (8)	0.0021 (7)
C38	0.0377 (10)	0.0360 (10)	0.0431 (10)	0.0017 (8)	0.0120 (8)	0.0041 (8)
C39	0.0550 (13)	0.0318 (10)	0.0672 (14)	0.0017 (9)	0.0199 (11)	−0.0030 (9)
C40	0.0708 (16)	0.0388 (11)	0.0610 (14)	−0.0169 (11)	0.0181 (12)	−0.0129 (10)
C41	0.0510 (12)	0.0506 (12)	0.0471 (11)	−0.0193 (10)	0.0016 (10)	−0.0020 (9)
C42	0.0365 (11)	0.0541 (13)	0.0649 (14)	0.0035 (9)	−0.0064 (10)	0.0050 (11)

S1—O2	1.4257 (14)	S2—O6	1.4270 (14)
S1—O1	1.4319 (13)	S2—O5	1.4296 (13)
S1—N1	1.6406 (14)	S2—N5	1.6436 (15)
S1—C1	1.7659 (17)	S2—C22	1.7684 (18)
O3—C13	1.2302 (19)	O7—C34	1.2314 (19)
O4—C17	1.367 (2)	O8—C38	1.375 (3)
O4—C21	1.415 (2)	O8—C42	1.425 (3)
N1—C8	1.4250 (19)	N5—C29	1.429 (2)
N1—C11	1.473 (2)	N5—C32	1.478 (2)
N2—C7	1.340 (2)	N6—C28	1.337 (2)
N2—N3	1.3547 (19)	N6—N7	1.3592 (18)
N3—C9	1.356 (2)	N7—C30	1.353 (2)
N3—C12	1.4462 (19)	N7—C33	1.4461 (19)
N4—C13	1.331 (2)	N8—C34	1.327 (2)
N4—C14	1.453 (2)	N8—C35	1.464 (2)
N4—H4N	0.8800	N8—H8N	0.8800
C1—C2	1.387 (2)	C22—C23	1.387 (2)
C1—C6	1.404 (2)	C22—C27	1.408 (2)
C2—C3	1.381 (3)	C23—C24	1.378 (3)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.385 (3)	C24—C25	1.387 (3)
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.383 (3)	C25—C26	1.384 (2)
C4—H4	0.9500	C25—H25	0.9500
C5—C6	1.398 (2)	C26—C27	1.395 (2)
C5—H5	0.9500	C26—H26	0.9500
C6—C7	1.451 (2)	C27—C28	1.457 (2)
C7—C8	1.407 (2)	C28—C29	1.404 (2)
C8—C9	1.374 (2)	C29—C30	1.373 (2)
C9—C10	1.483 (2)	C30—C31	1.483 (2)
C10—H10A	0.9800	C31—H31A	0.9800
C10—H10B	0.9800	C31—H31B	0.9800
C10—H10C	0.9800	C31—H31C	0.9800
C11—H11A	0.9800	C32—H32A	0.9800
C11—H11B	0.9800	C32—H32B	0.9800
C11—H11C	0.9800	C32—H32C	0.9800
C12—C13	1.521 (2)	C33—C34	1.524 (2)
C12—H12A	0.9900	C33—H33A	0.9900
C12—H12B	0.9900	C33—H33B	0.9900
C14—C15	1.508 (2)	C35—C36	1.506 (3)
C14—H14A	0.9900	C35—H35A	0.9900
C14—H14B	0.9900	C35—H35B	0.9900
C15—C20	1.391 (2)	C36—C41	1.386 (3)
C15—C16	1.391 (2)	C36—C37	1.392 (3)
C16—C17	1.392 (2)	C37—C38	1.387 (3)
C16—H16	0.9500	C37—H37	0.9500
C17—C18	1.384 (2)	C38—C39	1.393 (3)
C18—C19	1.375 (3)	C39—C40	1.370 (4)
C18—H18	0.9500	C39—H39	0.9500
C19—C20	1.388 (3)	C40—C41	1.395 (3)
C19—H19	0.9500	C40—H40	0.9500
C20—H20	0.9500	C41—H41	0.9500
C21—H21A	0.9800	C42—H42A	0.9800
C21—H21B	0.9800	C42—H42B	0.9800
C21—H21C	0.9800	C42—H42C	0.9800
O2—S1—O1	118.99 (9)	O6—S2—O5	119.27 (9)
O2—S1—N1	107.99 (8)	O6—S2—N5	107.37 (8)
O1—S1—N1	107.54 (8)	O5—S2—N5	107.64 (8)
O2—S1—C1	106.52 (8)	O6—S2—C22	106.94 (8)
O1—S1—C1	109.78 (8)	O5—S2—C22	110.05 (9)
N1—S1—C1	105.20 (7)	N5—S2—C22	104.61 (8)
C17—O4—C21	118.06 (14)	C38—O8—C42	116.66 (15)
C8—N1—C11	117.85 (13)	C29—N5—C32	115.53 (14)
C8—N1—S1	112.72 (11)	C29—N5—S2	110.68 (11)
C11—N1—S1	119.23 (11)	C32—N5—S2	118.20 (12)
C7—N2—N3	103.82 (12)	C28—N6—N7	103.79 (12)
N2—N3—C9	114.16 (12)	C30—N7—N6	113.93 (12)
N2—N3—C12	118.52 (13)	C30—N7—C33	127.25 (13)
C9—N3—C12	127.16 (14)	N6—N7—C33	118.60 (12)
C13—N4—C14	121.04 (13)	C34—N8—C35	123.75 (14)
C13—N4—H4N	119.5	C34—N8—H8N	118.1
C14—N4—H4N	119.5	C35—N8—H8N	118.1
C2—C1—C6	121.61 (16)	C23—C22—C27	121.50 (17)
C2—C1—S1	119.22 (13)	C23—C22—S2	120.63 (15)
C6—C1—S1	119.08 (12)	C27—C22—S2	117.79 (12)
C3—C2—C1	119.14 (17)	C24—C23—C22	119.02 (18)
C3—C2—H2	120.4	C24—C23—H23	120.5
C1—C2—H2	120.4	C22—C23—H23	120.5
C2—C3—C4	120.21 (17)	C23—C24—C25	120.53 (17)
C2—C3—H3	119.9	C23—C24—H24	119.7
C4—C3—H3	119.9	C25—C24—H24	119.7
C5—C4—C3	120.80 (17)	C26—C25—C24	120.52 (19)
C5—C4—H4	119.6	C26—C25—H25	119.7
C3—C4—H4	119.6	C24—C25—H25	119.7
C4—C5—C6	120.19 (16)	C25—C26—C27	120.24 (18)
C4—C5—H5	119.9	C25—C26—H26	119.9
C6—C5—H5	119.9	C27—C26—H26	119.9
C5—C6—C1	117.99 (15)	C26—C27—C22	118.10 (15)
C5—C6—C7	123.80 (15)	C26—C27—C28	123.83 (15)
C1—C6—C7	117.92 (14)	C22—C27—C28	117.91 (15)
N2—C7—C8	110.69 (14)	N6—C28—C29	110.78 (14)
N2—C7—C6	125.17 (14)	N6—C28—C27	125.66 (14)
C8—C7—C6	123.98 (14)	C29—C28—C27	123.52 (14)
C9—C8—C7	106.65 (13)	C30—C29—C28	106.71 (14)
C9—C8—N1	128.31 (14)	C30—C29—N5	128.52 (15)
C7—C8—N1	124.90 (14)	C28—C29—N5	124.72 (14)
N3—C9—C8	104.64 (14)	N7—C30—C29	104.76 (13)
N3—C9—C10	123.84 (14)	N7—C30—C31	124.18 (15)
C8—C9—C10	131.52 (15)	C29—C30—C31	131.01 (15)
C9—C10—H10A	109.5	C30—C31—H31A	109.5
C9—C10—H10B	109.5	C30—C31—H31B	109.5
H10A—C10—H10B	109.5	H31A—C31—H31B	109.5
C9—C10—H10C	109.5	C30—C31—H31C	109.5
H10A—C10—H10C	109.5	H31A—C31—H31C	109.5
H10B—C10—H10C	109.5	H31B—C31—H31C	109.5
N1—C11—H11A	109.5	N5—C32—H32A	109.5
N1—C11—H11B	109.5	N5—C32—H32B	109.5
H11A—C11—H11B	109.5	H32A—C32—H32B	109.5
N1—C11—H11C	109.5	N5—C32—H32C	109.5
H11A—C11—H11C	109.5	H32A—C32—H32C	109.5
H11B—C11—H11C	109.5	H32B—C32—H32C	109.5
N3—C12—C13	111.23 (13)	N7—C33—C34	110.42 (13)
N3—C12—H12A	109.4	N7—C33—H33A	109.6
C13—C12—H12A	109.4	C34—C33—H33A	109.6
N3—C12—H12B	109.4	N7—C33—H33B	109.6
C13—C12—H12B	109.4	C34—C33—H33B	109.6
H12A—C12—H12B	108.0	H33A—C33—H33B	108.1
O3—C13—N4	124.14 (15)	O7—C34—N8	124.70 (15)
O3—C13—C12	121.12 (14)	O7—C34—C33	121.08 (14)
N4—C13—C12	114.73 (13)	N8—C34—C33	114.21 (13)
N4—C14—C15	114.83 (13)	N8—C35—C36	110.90 (14)
N4—C14—H14A	108.6	N8—C35—H35A	109.5
C15—C14—H14A	108.6	C36—C35—H35A	109.5
N4—C14—H14B	108.6	N8—C35—H35B	109.5
C15—C14—H14B	108.6	C36—C35—H35B	109.5
H14A—C14—H14B	107.5	H35A—C35—H35B	108.0
C20—C15—C16	119.23 (15)	C41—C36—C37	119.54 (19)
C20—C15—C14	117.34 (15)	C41—C36—C35	121.41 (19)
C16—C15—C14	123.39 (15)	C37—C36—C35	119.03 (17)
C15—C16—C17	119.81 (16)	C38—C37—C36	120.55 (17)
C15—C16—H16	120.1	C38—C37—H37	119.7
C17—C16—H16	120.1	C36—C37—H37	119.7
O4—C17—C18	115.50 (15)	O8—C38—C37	123.90 (18)
O4—C17—C16	123.79 (16)	O8—C38—C39	116.50 (18)
C18—C17—C16	120.71 (16)	C37—C38—C39	119.6 (2)
C19—C18—C17	119.30 (16)	C40—C39—C38	119.8 (2)
C19—C18—H18	120.4	C40—C39—H39	120.1
C17—C18—H18	120.4	C38—C39—H39	120.1
C18—C19—C20	120.76 (17)	C39—C40—C41	121.0 (2)
C18—C19—H19	119.6	C39—C40—H40	119.5
C20—C19—H19	119.6	C41—C40—H40	119.5
C19—C20—C15	120.16 (17)	C36—C41—C40	119.5 (2)
C19—C20—H20	119.9	C36—C41—H41	120.2
C15—C20—H20	119.9	C40—C41—H41	120.2
O4—C21—H21A	109.5	O8—C42—H42A	109.5
O4—C21—H21B	109.5	O8—C42—H42B	109.5
H21A—C21—H21B	109.5	H42A—C42—H42B	109.5
O4—C21—H21C	109.5	O8—C42—H42C	109.5
H21A—C21—H21C	109.5	H42A—C42—H42C	109.5
H21B—C21—H21C	109.5	H42B—C42—H42C	109.5
O2—S1—N1—C8	−70.02 (13)	O6—S2—N5—C29	−64.49 (13)
O1—S1—N1—C8	160.41 (12)	O5—S2—N5—C29	165.94 (12)
C1—S1—N1—C8	43.43 (13)	C22—S2—N5—C29	48.89 (13)
O2—S1—N1—C11	145.41 (13)	O6—S2—N5—C32	159.02 (14)
O1—S1—N1—C11	15.84 (15)	O5—S2—N5—C32	29.45 (16)
C1—S1—N1—C11	−101.13 (14)	C22—S2—N5—C32	−87.59 (14)
C7—N2—N3—C9	−1.96 (17)	C28—N6—N7—C30	−1.62 (17)
C7—N2—N3—C12	−177.68 (13)	C28—N6—N7—C33	−176.66 (13)
O2—S1—C1—C2	−99.39 (15)	O6—S2—C22—C23	−103.66 (15)
O1—S1—C1—C2	30.69 (17)	O5—S2—C22—C23	27.27 (18)
N1—S1—C1—C2	146.13 (14)	N5—S2—C22—C23	142.65 (15)
O2—S1—C1—C6	77.32 (14)	O6—S2—C22—C27	73.01 (15)
O1—S1—C1—C6	−152.60 (13)	O5—S2—C22—C27	−156.06 (13)
N1—S1—C1—C6	−37.16 (15)	N5—S2—C22—C27	−40.69 (15)
C6—C1—C2—C3	−1.9 (3)	C27—C22—C23—C24	−2.3 (3)
S1—C1—C2—C3	174.73 (15)	S2—C22—C23—C24	174.25 (15)
C1—C2—C3—C4	−0.4 (3)	C22—C23—C24—C25	−0.4 (3)
C2—C3—C4—C5	1.7 (3)	C23—C24—C25—C26	2.1 (3)
C3—C4—C5—C6	−0.7 (3)	C24—C25—C26—C27	−1.1 (3)
C4—C5—C6—C1	−1.5 (2)	C25—C26—C27—C22	−1.5 (2)
C4—C5—C6—C7	172.30 (16)	C25—C26—C27—C28	173.67 (16)
C2—C1—C6—C5	2.8 (2)	C23—C22—C27—C26	3.2 (2)
S1—C1—C6—C5	−173.81 (12)	S2—C22—C27—C26	−173.39 (12)
C2—C1—C6—C7	−171.34 (15)	C23—C22—C27—C28	−172.24 (16)
S1—C1—C6—C7	12.0 (2)	S2—C22—C27—C28	11.1 (2)
N3—N2—C7—C8	0.75 (17)	N7—N6—C28—C29	1.21 (17)
N3—N2—C7—C6	−174.70 (14)	N7—N6—C28—C27	−176.35 (15)
C5—C6—C7—N2	10.3 (2)	C26—C27—C28—N6	14.7 (3)
C1—C6—C7—N2	−175.85 (15)	C22—C27—C28—N6	−170.05 (15)
C5—C6—C7—C8	−164.52 (16)	C26—C27—C28—C29	−162.53 (16)
C1—C6—C7—C8	9.3 (2)	C22—C27—C28—C29	12.7 (2)
N2—C7—C8—C9	0.62 (18)	N6—C28—C29—C30	−0.46 (18)
C6—C7—C8—C9	176.14 (14)	C27—C28—C29—C30	177.17 (15)
N2—C7—C8—N1	−175.25 (15)	N6—C28—C29—N5	−178.22 (15)
C6—C7—C8—N1	0.3 (3)	C27—C28—C29—N5	−0.6 (3)
C11—N1—C8—C9	−60.2 (2)	C32—N5—C29—C30	−73.5 (2)
S1—N1—C8—C9	154.68 (14)	S2—N5—C29—C30	148.71 (15)
C11—N1—C8—C7	114.74 (18)	C32—N5—C29—C28	103.7 (2)
S1—N1—C8—C7	−30.4 (2)	S2—N5—C29—C28	−34.0 (2)
N2—N3—C9—C8	2.36 (18)	N6—N7—C30—C29	1.36 (18)
C12—N3—C9—C8	177.63 (14)	C33—N7—C30—C29	175.89 (14)
N2—N3—C9—C10	−177.77 (15)	N6—N7—C30—C31	179.17 (15)
C12—N3—C9—C10	−2.5 (3)	C33—N7—C30—C31	−6.3 (3)
C7—C8—C9—N3	−1.71 (17)	C28—C29—C30—N7	−0.52 (17)
N1—C8—C9—N3	173.98 (15)	N5—C29—C30—N7	177.14 (16)
C7—C8—C9—C10	178.43 (17)	C28—C29—C30—C31	−178.12 (17)
N1—C8—C9—C10	−5.9 (3)	N5—C29—C30—C31	−0.5 (3)
N2—N3—C12—C13	82.23 (17)	C30—N7—C33—C34	−101.77 (18)
C9—N3—C12—C13	−92.87 (19)	N6—N7—C33—C34	72.54 (17)
C14—N4—C13—O3	3.8 (2)	C35—N8—C34—O7	−1.8 (3)
C14—N4—C13—C12	−175.58 (14)	C35—N8—C34—C33	179.52 (15)
N3—C12—C13—O3	26.5 (2)	N7—C33—C34—O7	44.81 (19)
N3—C12—C13—N4	−154.08 (14)	N7—C33—C34—N8	−136.44 (14)
C13—N4—C14—C15	−171.18 (14)	C34—N8—C35—C36	−132.81 (17)
N4—C14—C15—C20	169.04 (15)	N8—C35—C36—C41	119.73 (19)
N4—C14—C15—C16	−13.3 (2)	N8—C35—C36—C37	−61.8 (2)
C20—C15—C16—C17	−1.1 (3)	C41—C36—C37—C38	0.2 (3)
C14—C15—C16—C17	−178.74 (16)	C35—C36—C37—C38	−178.29 (16)
C21—O4—C17—C18	169.25 (18)	C42—O8—C38—C37	7.5 (3)
C21—O4—C17—C16	−10.9 (3)	C42—O8—C38—C39	−173.53 (18)
C15—C16—C17—O4	−177.66 (16)	C36—C37—C38—O8	−179.58 (16)
C15—C16—C17—C18	2.1 (3)	C36—C37—C38—C39	1.5 (3)
O4—C17—C18—C19	178.50 (17)	O8—C38—C39—C40	179.12 (18)
C16—C17—C18—C19	−1.3 (3)	C37—C38—C39—C40	−1.9 (3)
C17—C18—C19—C20	−0.5 (3)	C38—C39—C40—C41	0.6 (3)
C18—C19—C20—C15	1.5 (3)	C37—C36—C41—C40	−1.4 (3)
C16—C15—C20—C19	−0.7 (3)	C35—C36—C41—C40	176.98 (18)
C14—C15—C20—C19	177.06 (16)	C39—C40—C41—C36	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O7i	0.88	2.12	2.9511 (17)	158
N8—H8N···O3ii	0.88	2.02	2.8928 (18)	171
C10—H10C···O6iii	0.98	2.45	3.349 (2)	152
C12—H12A···O7i	0.99	2.56	3.2099 (19)	123
C14—H14A···N6ii	0.99	2.58	3.556 (2)	168
C16—H16···O7i	0.95	2.43	3.369 (2)	172
C25—H25···O4iv	0.95	2.47	3.365 (2)	156
C31—H31C···O2v	0.98	2.49	3.203 (2)	129
C33—H33A···O3ii	0.99	2.46	3.320 (2)	145
C33—H33B···O5vi	0.99	2.45	3.352 (2)	151
C40—H40···O2	0.95	2.59	3.367 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯O7i	0.88	2.12	2.9511 (17)	158
N8—H8N⋯O3ii	0.88	2.02	2.8928 (18)	171
C10—H10C⋯O6iii	0.98	2.45	3.349 (2)	152
C12—H12A⋯O7i	0.99	2.56	3.2099 (19)	123
C14—H14A⋯N6ii	0.99	2.58	3.556 (2)	168
C16—H16⋯O7i	0.95	2.43	3.369 (2)	172
C25—H25⋯O4iv	0.95	2.47	3.365 (2)	156
C31—H31C⋯O2v	0.98	2.49	3.203 (2)	129
C33—H33A⋯O3ii	0.99	2.46	3.320 (2)	145
C33—H33B⋯O5vi	0.99	2.45	3.352 (2)	151
C40—H40⋯O2	0.95	2.59	3.367 (3)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .