2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zin-2-yl)-N'-(3-meth-oxy-benzyl-idene)aceto-hydrazide dimethyl-formamide hemisolvate.

In the title compound, C(21)H(21)N(5)O(4)S·0.5C(3)H(7)NO, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by -0.451 (5) and 0.233 (5) Å, respectively, from the plane formed by the remaining ring atoms. The asymmetric unit contains a disordered half-mol-ecule of solvent lying close to inversion centers. The crystal structure is stabilized by weak inter-molecular N-H⋯O and C-H⋯O inter-actions.

Related literature

For related structures, see: Ahmad et al. (2008 ▶; 2009 ▶, 2011 ▶); Siddiqui et al. (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C21H21N5O4S·0.5C3H7NO

M = 476.04

Orthorhombic,

a = 18.3806 (5) Å

b = 8.1155 (2) Å

c = 30.4715 (5) Å

V = 4545.37 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 173 K

0.16 × 0.14 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.971, T max = 0.989

7438 measured reflections

3997 independent reflections

2747 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.125

S = 1.09

3997 reflections

328 parameters

35 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.34 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/S1600536810052177/jh2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052177/jh2242Isup2.hkl

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

C21H21N5O4S·0.5C3H7NO	F(000) = 2000
Mr = 476.04	Dx = 1.391 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5739 reflections
a = 18.3806 (5) Å	θ = 1.0–27.5°
b = 8.1155 (2) Å	µ = 0.19 mm−1
c = 30.4715 (5) Å	T = 173 K
V = 4545.37 (18) Å3	Plate, colorless
Z = 8	0.16 × 0.14 × 0.06 mm

Nonius KappaCCD diffractometer	3997 independent reflections
Radiation source: fine-focus sealed tube	2747 reflections with I > 2σ(I)
graphite	Rint = 0.052
ω and φ scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −21→21
Tmin = 0.971, Tmax = 0.989	k = −9→9
7438 measured reflections	l = −36→36

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0337P)2 + 4.9015P] where P = (Fo2 + 2Fc2)/3
3997 reflections	(Δ/σ)max < 0.001
328 parameters	Δρmax = 0.21 e Å−3
35 restraints	Δρmin = −0.34 e Å−3

Experimental. N'-[(3-Methoxyphenyl)methylidene]-2-(3,4-dimethyl-5,5- dioxidopyrazolo[4,3-c][1,2]benzothiazin-1(4H)-yl)acetohydrazide: White powder; mp 495–496 K. IR (KBr) cm-1: 3449; 3364; 3033; 1692; 1616; 1310; 1164. 1H-NMR (DMSO-d6) (500 MHz) δ: 2.32 (3H, s, CCH3), 2.78 (3H, s, OCH3), 2.98 (3H, s, NCH3), 5.52 (2H, s, NCH2), 6.99–7.02 (1H, dd, J = 8.2, 2.0 Hz, ArH), 7.26–7.38 (3H, m, ArH), 7.63 (1H, t, J = 7.8 Hz, ArH), 7.76 (1H, t, J = 7.6 Hz, ArH), 7.87 (1H, d, J = 7.8 Hz, ArH), 7.93 (1H, d, J = 7.7 Hz, ArH), 8.03 (1H, s, N═CH), 11.79 (1H, br s, NH). 13C NMR: 8.5, 38.9, 47.3, 51.6, 110.5, 113.6, 117.8, 123.1, 124.1, 124.5, 126.2, 126.7, 127.5, 128.3, 130.1, 131.8, 133.4, 134.2, 136.9, 139.3, 157.6, 165.7. MS m/z: 439.0(M+).

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	−0.11871 (4)	0.35139 (10)	0.21689 (2)	0.0292 (2)
O1	−0.17406 (11)	0.3405 (3)	0.24982 (7)	0.0414 (6)
O2	−0.10532 (11)	0.2115 (3)	0.18941 (7)	0.0354 (5)
O3	0.18352 (11)	0.3040 (3)	0.13232 (7)	0.0337 (5)
O4	0.49365 (13)	0.4478 (3)	−0.07548 (7)	0.0526 (7)
N1	−0.04176 (13)	0.3984 (3)	0.24142 (7)	0.0284 (6)
N2	0.05545 (13)	0.6057 (3)	0.15386 (8)	0.0296 (6)
N3	0.10980 (13)	0.5444 (3)	0.17947 (8)	0.0294 (6)
N4	0.25112 (15)	0.5050 (3)	0.10038 (8)	0.0360 (6)
H4N	0.2668	0.6072	0.1021	0.043*
N5	0.27351 (14)	0.4044 (3)	0.06600 (8)	0.0355 (7)
C1	−0.13703 (16)	0.5190 (4)	0.18165 (9)	0.0260 (7)
C2	−0.20868 (17)	0.5616 (4)	0.17262 (10)	0.0318 (7)
H2	−0.2475	0.5085	0.1875	0.038*
C3	−0.22292 (18)	0.6821 (4)	0.14170 (10)	0.0372 (8)
H3	−0.2718	0.7100	0.1348	0.045*
C4	−0.16594 (18)	0.7623 (4)	0.12073 (10)	0.0382 (8)
H4	−0.1761	0.8442	0.0993	0.046*
C5	−0.09438 (17)	0.7241 (4)	0.13074 (9)	0.0329 (8)
H5	−0.0558	0.7820	0.1169	0.040*
C6	−0.07912 (16)	0.6004 (4)	0.16124 (9)	0.0261 (7)
C7	−0.00550 (16)	0.5566 (4)	0.17436 (9)	0.0255 (7)
C8	0.01144 (16)	0.4621 (4)	0.21164 (9)	0.0257 (7)
C9	−0.04416 (17)	0.4735 (4)	0.28542 (9)	0.0341 (8)
H9A	0.0044	0.4690	0.2987	0.051*
H9B	−0.0787	0.4128	0.3039	0.051*
H9C	−0.0598	0.5885	0.2830	0.051*
C10	0.08623 (16)	0.4549 (4)	0.21424 (9)	0.0283 (7)
C11	0.13593 (17)	0.3754 (4)	0.24619 (11)	0.0394 (8)
H11A	0.1697	0.3027	0.2306	0.059*
H11B	0.1074	0.3107	0.2672	0.059*
H11C	0.1635	0.4603	0.2619	0.059*
C12	0.18383 (16)	0.5714 (4)	0.16510 (10)	0.0350 (8)
H12A	0.2170	0.5634	0.1906	0.042*
H12B	0.1883	0.6836	0.1526	0.042*
C13	0.20561 (16)	0.4462 (4)	0.13096 (9)	0.0282 (7)
C14	0.31843 (18)	0.4724 (4)	0.03961 (10)	0.0369 (8)
H14	0.3353	0.5807	0.0457	0.044*
C15	0.34450 (19)	0.3878 (4)	0.00032 (10)	0.0374 (8)
C16	0.40459 (19)	0.4517 (4)	−0.02106 (10)	0.0404 (9)
H16	0.4265	0.5499	−0.0104	0.048*
C17	0.43339 (18)	0.3744 (4)	−0.05791 (10)	0.0386 (8)
C18	0.4008 (2)	0.2342 (5)	−0.07389 (10)	0.0452 (9)
H18	0.4200	0.1807	−0.0991	0.054*
C19	0.3398 (2)	0.1714 (5)	−0.05311 (11)	0.0507 (10)
H19	0.3171	0.0751	−0.0645	0.061*
C20	0.3111 (2)	0.2460 (5)	−0.01617 (11)	0.0467 (9)
H20	0.2693	0.2016	−0.0022	0.056*
C21	0.5293 (2)	0.3652 (6)	−0.11094 (11)	0.0629 (12)
H21A	0.5449	0.2555	−0.1013	0.094*
H21B	0.5719	0.4291	−0.1201	0.094*
H21C	0.4956	0.3543	−0.1357	0.094*
O5	0.1045 (7)	0.3207 (11)	0.0100 (4)	0.161 (5)	0.50
N6	0.0164 (11)	0.498 (3)	0.0059 (7)	0.089 (5)	0.50
C22	0.0794 (11)	0.4396 (18)	0.0258 (4)	0.130 (5)	0.50
H22	0.1006	0.4925	0.0505	0.156*	0.50
C23	−0.0119 (7)	0.401 (2)	−0.0349 (5)	0.078 (3)	0.50
H23A	−0.0556	0.4548	−0.0465	0.117*	0.50
H23B	−0.0238	0.2876	−0.0263	0.117*	0.50
H23C	0.0259	0.3988	−0.0576	0.117*	0.50
C24	−0.0275 (10)	0.6312 (17)	0.0173 (7)	0.159 (8)	0.50
H24A	−0.0674	0.6410	−0.0039	0.239*	0.50
H24B	0.0016	0.7324	0.0170	0.239*	0.50
H24C	−0.0474	0.6138	0.0467	0.239*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0220 (4)	0.0321 (4)	0.0333 (4)	−0.0047 (4)	0.0012 (3)	0.0040 (3)
O1	0.0275 (12)	0.0564 (15)	0.0402 (12)	−0.0078 (12)	0.0080 (10)	0.0124 (11)
O2	0.0345 (13)	0.0265 (12)	0.0451 (13)	−0.0030 (10)	−0.0045 (10)	−0.0017 (10)
O3	0.0305 (12)	0.0252 (13)	0.0455 (13)	−0.0014 (10)	0.0076 (10)	−0.0047 (10)
O4	0.0473 (16)	0.0686 (19)	0.0421 (13)	0.0044 (14)	0.0185 (12)	0.0017 (13)
N1	0.0229 (14)	0.0368 (15)	0.0256 (13)	−0.0031 (12)	0.0010 (10)	0.0006 (11)
N2	0.0238 (15)	0.0303 (15)	0.0346 (14)	−0.0017 (12)	0.0051 (11)	−0.0032 (12)
N3	0.0205 (14)	0.0300 (15)	0.0377 (14)	−0.0013 (12)	0.0052 (11)	−0.0047 (12)
N4	0.0389 (16)	0.0227 (14)	0.0463 (15)	−0.0037 (13)	0.0149 (13)	−0.0102 (12)
N5	0.0354 (17)	0.0310 (16)	0.0400 (15)	0.0041 (13)	0.0079 (12)	−0.0083 (12)
C1	0.0223 (17)	0.0307 (18)	0.0249 (15)	0.0032 (14)	0.0007 (12)	−0.0020 (13)
C2	0.0256 (18)	0.0358 (19)	0.0338 (17)	0.0008 (15)	0.0040 (13)	−0.0047 (15)
C3	0.0298 (18)	0.041 (2)	0.0408 (19)	0.0104 (16)	−0.0015 (14)	−0.0012 (16)
C4	0.042 (2)	0.039 (2)	0.0342 (18)	0.0098 (17)	0.0012 (15)	0.0057 (15)
C5	0.0327 (19)	0.0325 (19)	0.0336 (17)	0.0010 (16)	0.0063 (14)	0.0010 (14)
C6	0.0244 (17)	0.0272 (17)	0.0267 (16)	0.0011 (14)	0.0029 (12)	−0.0050 (13)
C7	0.0222 (17)	0.0253 (17)	0.0289 (16)	−0.0019 (14)	0.0048 (12)	−0.0049 (13)
C8	0.0225 (17)	0.0266 (17)	0.0279 (16)	−0.0011 (14)	0.0009 (12)	−0.0007 (13)
C9	0.037 (2)	0.0392 (19)	0.0262 (16)	0.0007 (16)	0.0005 (14)	0.0034 (14)
C10	0.0238 (17)	0.0263 (17)	0.0348 (17)	−0.0010 (14)	0.0018 (13)	−0.0068 (14)
C11	0.0276 (18)	0.042 (2)	0.0482 (19)	0.0034 (17)	−0.0077 (14)	−0.0043 (17)
C12	0.0200 (18)	0.0377 (19)	0.0474 (19)	−0.0050 (15)	0.0113 (14)	−0.0116 (15)
C13	0.0201 (17)	0.0284 (18)	0.0362 (17)	−0.0007 (14)	0.0000 (13)	−0.0033 (14)
C14	0.039 (2)	0.0326 (19)	0.0396 (19)	0.0006 (17)	0.0089 (15)	−0.0040 (15)
C15	0.038 (2)	0.037 (2)	0.0371 (18)	0.0060 (17)	0.0049 (15)	0.0006 (15)
C16	0.041 (2)	0.040 (2)	0.0399 (19)	0.0023 (17)	0.0062 (16)	0.0011 (16)
C17	0.039 (2)	0.045 (2)	0.0317 (18)	0.0109 (18)	0.0045 (15)	0.0038 (16)
C18	0.050 (2)	0.055 (2)	0.0301 (18)	0.012 (2)	−0.0006 (16)	−0.0068 (17)
C19	0.056 (3)	0.056 (3)	0.040 (2)	−0.004 (2)	−0.0008 (18)	−0.0129 (18)
C20	0.046 (2)	0.054 (2)	0.040 (2)	−0.006 (2)	0.0046 (16)	−0.0066 (18)
C21	0.056 (3)	0.094 (3)	0.038 (2)	0.013 (3)	0.0173 (18)	−0.002 (2)
O5	0.238 (13)	0.067 (6)	0.178 (10)	−0.008 (7)	−0.069 (9)	0.021 (6)
N6	0.149 (15)	0.046 (4)	0.071 (10)	−0.037 (9)	0.058 (8)	−0.009 (6)
C22	0.226 (16)	0.069 (8)	0.094 (9)	−0.058 (9)	−0.033 (8)	0.025 (7)
C23	0.077 (9)	0.067 (7)	0.090 (8)	0.001 (6)	0.021 (6)	0.011 (5)
C24	0.207 (19)	0.052 (9)	0.22 (2)	−0.043 (9)	0.168 (16)	−0.024 (11)

S1—O1	1.432 (2)	C10—C11	1.483 (4)
S1—O2	1.432 (2)	C11—H11A	0.9800
S1—N1	1.645 (2)	C11—H11B	0.9800
S1—C1	1.765 (3)	C11—H11C	0.9800
O3—C13	1.224 (4)	C12—C13	1.508 (4)
O4—C17	1.367 (4)	C12—H12A	0.9900
O4—C21	1.431 (4)	C12—H12B	0.9900
N1—C8	1.431 (4)	C14—C15	1.461 (4)
N1—C9	1.473 (4)	C14—H14	0.9500
N2—C7	1.343 (4)	C15—C16	1.383 (5)
N2—N3	1.362 (3)	C15—C20	1.398 (5)
N3—C10	1.356 (4)	C16—C17	1.391 (4)
N3—C12	1.446 (4)	C16—H16	0.9500
N4—C13	1.340 (4)	C17—C18	1.375 (5)
N4—N5	1.390 (3)	C18—C19	1.386 (5)
N4—H4N	0.8800	C18—H18	0.9500
N5—C14	1.278 (4)	C19—C20	1.382 (5)
C1—C2	1.389 (4)	C19—H19	0.9500
C1—C6	1.399 (4)	C20—H20	0.9500
C2—C3	1.383 (4)	C21—H21A	0.9800
C2—H2	0.9500	C21—H21B	0.9800
C3—C4	1.389 (5)	C21—H21C	0.9800
C3—H3	0.9500	O5—C22	1.173 (18)
C4—C5	1.385 (4)	N6—C22	1.39 (2)
C4—H4	0.9500	N6—C24	1.39 (3)
C5—C6	1.397 (4)	N6—C23	1.56 (3)
C5—H5	0.9500	C22—H22	0.9500
C6—C7	1.455 (4)	C23—H23A	0.9800
C7—C8	1.405 (4)	C23—H23B	0.9800
C8—C10	1.378 (4)	C23—H23C	0.9800
C9—H9A	0.9800	C24—H24A	0.9800
C9—H9B	0.9800	C24—H24B	0.9800
C9—H9C	0.9800	C24—H24C	0.9800
O1—S1—O2	118.88 (14)	H11B—C11—H11C	109.5
O1—S1—N1	107.87 (13)	N3—C12—C13	110.9 (3)
O2—S1—N1	107.57 (13)	N3—C12—H12A	109.5
O1—S1—C1	109.78 (14)	C13—C12—H12A	109.5
O2—S1—C1	106.74 (13)	N3—C12—H12B	109.5
N1—S1—C1	105.18 (13)	C13—C12—H12B	109.5
C17—O4—C21	117.6 (3)	H12A—C12—H12B	108.0
C8—N1—C9	116.6 (2)	O3—C13—N4	124.5 (3)
C8—N1—S1	112.53 (18)	O3—C13—C12	121.6 (3)
C9—N1—S1	118.9 (2)	N4—C13—C12	113.9 (3)
C7—N2—N3	103.7 (2)	N5—C14—C15	121.6 (3)
C10—N3—N2	114.1 (2)	N5—C14—H14	119.2
C10—N3—C12	128.2 (3)	C15—C14—H14	119.2
N2—N3—C12	117.5 (2)	C16—C15—C20	119.3 (3)
C13—N4—N5	120.0 (3)	C16—C15—C14	118.2 (3)
C13—N4—H4N	120.0	C20—C15—C14	122.5 (3)
N5—N4—H4N	120.0	C15—C16—C17	121.0 (3)
C14—N5—N4	114.3 (3)	C15—C16—H16	119.5
C2—C1—C6	121.1 (3)	C17—C16—H16	119.5
C2—C1—S1	119.5 (2)	O4—C17—C18	125.1 (3)
C6—C1—S1	119.3 (2)	O4—C17—C16	115.3 (3)
C3—C2—C1	119.4 (3)	C18—C17—C16	119.6 (3)
C3—C2—H2	120.3	C17—C18—C19	119.7 (3)
C1—C2—H2	120.3	C17—C18—H18	120.1
C2—C3—C4	120.1 (3)	C19—C18—H18	120.1
C2—C3—H3	119.9	C20—C19—C18	121.3 (4)
C4—C3—H3	119.9	C20—C19—H19	119.4
C5—C4—C3	120.6 (3)	C18—C19—H19	119.4
C5—C4—H4	119.7	C19—C20—C15	119.1 (3)
C3—C4—H4	119.7	C19—C20—H20	120.4
C4—C5—C6	119.9 (3)	C15—C20—H20	120.4
C4—C5—H5	120.1	O4—C21—H21A	109.5
C6—C5—H5	120.1	O4—C21—H21B	109.5
C5—C6—C1	118.9 (3)	H21A—C21—H21B	109.5
C5—C6—C7	123.0 (3)	O4—C21—H21C	109.5
C1—C6—C7	118.0 (3)	H21A—C21—H21C	109.5
N2—C7—C8	110.7 (3)	H21B—C21—H21C	109.5
N2—C7—C6	125.1 (3)	C22—N6—C24	130 (2)
C8—C7—C6	124.1 (3)	C22—N6—C23	116.9 (19)
C10—C8—C7	106.9 (3)	C24—N6—C23	113.4 (15)
C10—C8—N1	129.0 (3)	O5—C22—N6	115.5 (16)
C7—C8—N1	124.0 (3)	O5—C22—H22	122.3
N1—C9—H9A	109.5	N6—C22—H22	122.3
N1—C9—H9B	109.5	N6—C23—H23A	109.5
H9A—C9—H9B	109.5	N6—C23—H23B	109.5
N1—C9—H9C	109.5	H23A—C23—H23B	109.5
H9A—C9—H9C	109.5	N6—C23—H23C	109.5
H9B—C9—H9C	109.5	H23A—C23—H23C	109.5
N3—C10—C8	104.5 (3)	H23B—C23—H23C	109.5
N3—C10—C11	123.3 (3)	N6—C24—H24A	109.5
C8—C10—C11	132.1 (3)	N6—C24—H24B	109.5
C10—C11—H11A	109.5	H24A—C24—H24B	109.5
C10—C11—H11B	109.5	N6—C24—H24C	109.5
H11A—C11—H11B	109.5	H24A—C24—H24C	109.5
C10—C11—H11C	109.5	H24B—C24—H24C	109.5
H11A—C11—H11C	109.5
O1—S1—N1—C8	−161.7 (2)	C9—N1—C8—C10	65.6 (4)
O2—S1—N1—C8	68.9 (2)	S1—N1—C8—C10	−151.9 (3)
C1—S1—N1—C8	−44.6 (2)	C9—N1—C8—C7	−110.0 (3)
O1—S1—N1—C9	−20.2 (3)	S1—N1—C8—C7	32.6 (4)
O2—S1—N1—C9	−149.5 (2)	N2—N3—C10—C8	−1.6 (3)
C1—S1—N1—C9	97.0 (2)	C12—N3—C10—C8	−176.8 (3)
C7—N2—N3—C10	2.0 (3)	N2—N3—C10—C11	179.4 (3)
C7—N2—N3—C12	177.7 (3)	C12—N3—C10—C11	4.3 (5)
C13—N4—N5—C14	−178.1 (3)	C7—C8—C10—N3	0.5 (3)
O1—S1—C1—C2	−33.0 (3)	N1—C8—C10—N3	−175.6 (3)
O2—S1—C1—C2	97.1 (2)	C7—C8—C10—C11	179.4 (3)
N1—S1—C1—C2	−148.9 (2)	N1—C8—C10—C11	3.2 (6)
O1—S1—C1—C6	150.8 (2)	C10—N3—C12—C13	93.3 (4)
O2—S1—C1—C6	−79.1 (3)	N2—N3—C12—C13	−81.7 (3)
N1—S1—C1—C6	34.9 (3)	N5—N4—C13—O3	3.3 (5)
C6—C1—C2—C3	2.5 (5)	N5—N4—C13—C12	−177.7 (3)
S1—C1—C2—C3	−173.6 (2)	N3—C12—C13—O3	−35.0 (4)
C1—C2—C3—C4	−1.6 (5)	N3—C12—C13—N4	145.9 (3)
C2—C3—C4—C5	−0.6 (5)	N4—N5—C14—C15	−176.6 (3)
C3—C4—C5—C6	1.9 (5)	N5—C14—C15—C16	−165.5 (3)
C4—C5—C6—C1	−1.0 (4)	N5—C14—C15—C20	14.5 (5)
C4—C5—C6—C7	−178.2 (3)	C20—C15—C16—C17	−1.8 (5)
C2—C1—C6—C5	−1.2 (4)	C14—C15—C16—C17	178.1 (3)
S1—C1—C6—C5	174.9 (2)	C21—O4—C17—C18	−5.6 (5)
C2—C1—C6—C7	176.1 (3)	C21—O4—C17—C16	174.5 (3)
S1—C1—C6—C7	−7.7 (4)	C15—C16—C17—O4	−178.7 (3)
N3—N2—C7—C8	−1.6 (3)	C15—C16—C17—C18	1.4 (5)
N3—N2—C7—C6	175.9 (3)	O4—C17—C18—C19	179.9 (3)
C5—C6—C7—N2	−12.6 (5)	C16—C17—C18—C19	−0.1 (5)
C1—C6—C7—N2	170.1 (3)	C17—C18—C19—C20	−0.6 (5)
C5—C6—C7—C8	164.5 (3)	C18—C19—C20—C15	0.2 (6)
C1—C6—C7—C8	−12.7 (4)	C16—C15—C20—C19	1.1 (5)
N2—C7—C8—C10	0.7 (3)	C14—C15—C20—C19	−178.9 (3)
C6—C7—C8—C10	−176.8 (3)	C24—N6—C22—O5	178 (2)
N2—C7—C8—N1	177.1 (3)	C23—N6—C22—O5	−1(2)
C6—C7—C8—N1	−0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O3i	0.88	2.06	2.878 (3)	155
C14—H14···O5i	0.95	2.49	3.287 (10)	142
C16—H16···O5i	0.95	2.35	3.145 (11)	140
C21—H21C···O2ii	0.98	2.53	3.497 (5)	169
C9—H9B···O1	0.98	2.48	2.836 (4)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯O3i	0.88	2.06	2.878 (3)	155
C14—H14⋯O5i	0.95	2.49	3.287 (10)	142
C16—H16⋯O5i	0.95	2.35	3.145 (11)	140
C21—H21C⋯O2ii	0.98	2.53	3.497 (5)	169

Symmetry codes: (i) ; (ii) .