N-(1-Allyl-1H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

The asymmetric unit of the title compound, C17H17N3O2S, contains two independent mol-ecules linked by an N-H⋯O hydrogen bond. The mol-ecules show different conformations. In the first mol-ecule, the fused five- and six-membered ring system is almost perpendicular to the plane through the atoms forming the allyl group, as indicated by the dihedral angle of 85.1 (4)°. The dihedral angle with the methyl-benzene-sulfonamide group is 78.8 (1)°. On the other hand, in the second mol-ecule, the dihedral angles between the indazole plane and the allyl and methyl-benzene-sulfonamide groups are 80.3 (3) and 41.5 (1)°, respectively. In the crystal, mol-ecules are further linked by N-H⋯N and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological activity of sulfonamides, see: Bouissane et al. (2006 ▶); El-Sayed et al. (2011 ▶); Mustafa et al. (2012 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2013 ▶).

Experimental

Crystal data

C17H17N3O2S

M = 327.40

Triclinic,

a = 8.8200 (4) Å

b = 10.4769 (5) Å

c = 19.7407 (10) Å

α = 80.211 (1)°

β = 78.984 (1)°

γ = 69.784 (1)°

V = 1669.51 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.42 × 0.35 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.693, T max = 0.747

31703 measured reflections

6791 independent reflections

5368 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.02

6791 reflections

415 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813032091/im2445sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032091/im2445Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813032091/im2445Isup3.cml

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

C17H17N3O2S	Z = 4
Mr = 327.40	F(000) = 688
Triclinic, P1	Dx = 1.303 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8200 (4) Å	Cell parameters from 6791 reflections
b = 10.4769 (5) Å	θ = 2.4–26.4°
c = 19.7407 (10) Å	µ = 0.21 mm−1
α = 80.211 (1)°	T = 296 K
β = 78.984 (1)°	Block, colourless
γ = 69.784 (1)°	0.42 × 0.35 × 0.28 mm
V = 1669.51 (14) Å3

Bruker X8 APEX diffractometer	6791 independent reflections
Radiation source: fine-focus sealed tube	5368 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→11
Tmin = 0.693, Tmax = 0.747	k = −13→13
31703 measured reflections	l = −24→24

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.4278P] where P = (Fo2 + 2Fc2)/3
6791 reflections	(Δ/σ)max = 0.001
415 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.28 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 > 2σ(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
C1	−0.5331 (4)	1.4103 (5)	1.1048 (2)	0.1376 (14)
H1A	−0.4762	1.3460	1.1375	0.165*
H1B	−0.5362	1.5009	1.1007	0.165*
C2	−0.6054 (3)	1.3750 (3)	1.06626 (16)	0.0943 (8)
H2	−0.6610	1.4419	1.0341	0.113*
C3	−0.6085 (3)	1.2319 (3)	1.06826 (13)	0.0859 (7)
H3A	−0.5292	1.1694	1.0966	0.103*
H3B	−0.7156	1.2276	1.0894	0.103*
C4	−0.6237 (3)	1.1553 (3)	0.90373 (15)	0.0899 (8)
H4	−0.6796	1.1473	0.8701	0.108*
C5	−0.4527 (3)	1.1281 (2)	0.89489 (11)	0.0631 (5)
C6	−0.4237 (3)	1.1507 (2)	0.95842 (10)	0.0567 (5)
C7	−0.2677 (3)	1.1323 (2)	0.97123 (10)	0.0626 (5)
H7	−0.2500	1.1460	1.0140	0.075*
C8	−0.1409 (3)	1.0934 (2)	0.91886 (9)	0.0561 (5)
H8	−0.0355	1.0816	0.9260	0.067*
C9	−0.1670 (2)	1.07082 (18)	0.85424 (9)	0.0483 (4)
C10	−0.3201 (3)	1.0860 (2)	0.84226 (10)	0.0623 (5)
H10	−0.3363	1.0688	0.8000	0.075*
C11	0.0714 (2)	0.7588 (2)	0.81912 (10)	0.0537 (4)
C12	−0.0059 (3)	0.7344 (2)	0.77026 (12)	0.0680 (6)
H12	−0.0317	0.7982	0.7317	0.082*
C13	−0.0443 (3)	0.6161 (3)	0.77871 (15)	0.0810 (7)
H13	−0.0977	0.6011	0.7460	0.097*
C14	−0.0053 (3)	0.5185 (2)	0.83494 (16)	0.0806 (7)
C15	0.0682 (3)	0.5455 (3)	0.88345 (15)	0.0874 (8)
H15	0.0935	0.4814	0.9219	0.105*
C16	0.1063 (3)	0.6655 (2)	0.87706 (12)	0.0717 (6)
H16	0.1543	0.6826	0.9111	0.086*
C17	−0.0423 (4)	0.3862 (3)	0.8436 (2)	0.1211 (12)
H17A	−0.1549	0.4054	0.8394	0.182*
H17B	−0.0214	0.3383	0.8886	0.182*
H17C	0.0258	0.3305	0.8084	0.182*
C18	−0.0239 (3)	0.5553 (3)	0.40309 (16)	0.0876 (8)
H18A	−0.1103	0.5665	0.4393	0.105*
H18B	0.0332	0.4688	0.3894	0.105*
C19	0.0165 (3)	0.6589 (2)	0.37214 (12)	0.0632 (5)
H19	0.1036	0.6438	0.3362	0.076*
C20	−0.0659 (2)	0.80224 (19)	0.38962 (10)	0.0522 (4)
H20A	−0.1273	0.8559	0.3527	0.063*
H20B	−0.1423	0.8019	0.4320	0.063*
C21	0.2282 (2)	0.96925 (19)	0.36555 (9)	0.0511 (4)
H21	0.2911	1.0194	0.3383	0.061*
C22	0.2391 (2)	0.91991 (17)	0.43648 (8)	0.0428 (4)
C23	0.3346 (2)	0.92338 (17)	0.48490 (8)	0.0442 (4)
H23	0.4118	0.9684	0.4729	0.053*
C24	0.3107 (2)	0.85819 (16)	0.55050 (8)	0.0419 (4)
C25	0.1910 (2)	0.79282 (18)	0.56925 (9)	0.0484 (4)
H25	0.1768	0.7507	0.6143	0.058*
C26	0.0952 (2)	0.78944 (18)	0.52319 (9)	0.0488 (4)
H26	0.0158	0.7467	0.5361	0.059*
C27	0.1216 (2)	0.85298 (16)	0.45583 (8)	0.0407 (4)
C28	0.5359 (2)	0.58393 (18)	0.63513 (9)	0.0463 (4)
C29	0.5396 (2)	0.5001 (2)	0.58778 (10)	0.0552 (5)
H29	0.5773	0.5188	0.5411	0.066*
C30	0.4874 (3)	0.3886 (2)	0.60989 (11)	0.0619 (5)
H30	0.4889	0.3330	0.5775	0.074*
C31	0.4327 (2)	0.3571 (2)	0.67903 (11)	0.0590 (5)
C32	0.4335 (3)	0.4411 (2)	0.72592 (11)	0.0726 (6)
H32	0.3994	0.4207	0.7728	0.087*
C33	0.4837 (3)	0.5539 (2)	0.70484 (10)	0.0665 (6)
H33	0.4825	0.6095	0.7371	0.080*
C34	0.3732 (3)	0.2362 (3)	0.70195 (15)	0.0841 (7)
H34A	0.2562	0.2675	0.7115	0.126*
H34B	0.4174	0.1867	0.7432	0.126*
H34C	0.4081	0.1772	0.6658	0.126*
N1	−0.5718 (2)	1.18978 (19)	0.99908 (10)	0.0694 (5)
N2	−0.6939 (2)	1.1936 (2)	0.96546 (12)	0.0855 (6)
N3	−0.03312 (19)	1.03964 (16)	0.79882 (7)	0.0523 (4)
H3N	−0.0594	1.0518	0.7611	0.063*
N4	0.05029 (18)	0.86568 (15)	0.39871 (7)	0.0470 (3)
N5	0.1175 (2)	0.93510 (16)	0.34324 (7)	0.0521 (4)
N6	0.40966 (19)	0.85977 (15)	0.60082 (7)	0.0487 (4)
H6N	0.3615	0.8700	0.6388	0.058*
O1	0.22363 (18)	0.91011 (16)	0.73713 (7)	0.0677 (4)
O2	0.20026 (17)	0.91093 (16)	0.86333 (7)	0.0688 (4)
O3	0.67127 (17)	0.72657 (15)	0.53792 (8)	0.0677 (4)
O4	0.6511 (2)	0.76466 (16)	0.66010 (8)	0.0748 (4)
S1	0.12954 (6)	0.90722 (5)	0.80483 (2)	0.05223 (14)
S2	0.58344 (6)	0.73592 (5)	0.60662 (2)	0.05151 (14)

	U11	U22	U33	U12	U13	U23
C1	0.092 (2)	0.163 (4)	0.149 (3)	−0.015 (2)	0.001 (2)	−0.071 (3)
C2	0.0788 (17)	0.105 (2)	0.0888 (19)	−0.0081 (15)	0.0001 (15)	−0.0433 (17)
C3	0.0829 (16)	0.099 (2)	0.0613 (14)	−0.0196 (14)	0.0163 (12)	−0.0202 (13)
C4	0.0640 (14)	0.117 (2)	0.0809 (17)	−0.0096 (14)	−0.0194 (13)	−0.0214 (16)
C5	0.0589 (12)	0.0669 (13)	0.0564 (12)	−0.0073 (10)	−0.0145 (9)	−0.0089 (10)
C6	0.0649 (12)	0.0509 (11)	0.0464 (10)	−0.0117 (9)	−0.0036 (9)	−0.0046 (8)
C7	0.0738 (13)	0.0749 (14)	0.0397 (10)	−0.0214 (11)	−0.0072 (9)	−0.0148 (9)
C8	0.0629 (11)	0.0668 (12)	0.0418 (10)	−0.0212 (10)	−0.0109 (8)	−0.0104 (9)
C9	0.0598 (11)	0.0455 (10)	0.0361 (9)	−0.0112 (8)	−0.0090 (8)	−0.0054 (7)
C10	0.0628 (12)	0.0757 (14)	0.0446 (10)	−0.0091 (10)	−0.0179 (9)	−0.0141 (9)
C11	0.0500 (10)	0.0561 (11)	0.0461 (10)	−0.0064 (8)	−0.0039 (8)	−0.0082 (8)
C12	0.0773 (14)	0.0674 (14)	0.0587 (12)	−0.0190 (11)	−0.0152 (11)	−0.0090 (10)
C13	0.0810 (16)	0.0753 (16)	0.0906 (18)	−0.0244 (13)	−0.0089 (14)	−0.0253 (14)
C14	0.0586 (13)	0.0602 (14)	0.109 (2)	−0.0098 (11)	0.0117 (13)	−0.0202 (14)
C15	0.0765 (16)	0.0666 (15)	0.0922 (19)	−0.0075 (13)	−0.0019 (14)	0.0186 (13)
C16	0.0676 (13)	0.0738 (15)	0.0627 (13)	−0.0123 (11)	−0.0157 (11)	0.0060 (11)
C17	0.096 (2)	0.0656 (17)	0.186 (4)	−0.0242 (15)	0.022 (2)	−0.0225 (19)
C18	0.0931 (18)	0.0565 (14)	0.113 (2)	−0.0224 (13)	−0.0220 (16)	−0.0035 (13)
C19	0.0685 (13)	0.0618 (13)	0.0663 (13)	−0.0244 (10)	−0.0145 (10)	−0.0131 (10)
C20	0.0522 (10)	0.0506 (10)	0.0589 (11)	−0.0191 (8)	−0.0206 (9)	−0.0003 (8)
C21	0.0652 (11)	0.0579 (11)	0.0378 (9)	−0.0308 (9)	−0.0112 (8)	0.0015 (8)
C22	0.0522 (9)	0.0408 (9)	0.0368 (8)	−0.0165 (7)	−0.0081 (7)	−0.0034 (7)
C23	0.0528 (10)	0.0440 (9)	0.0401 (9)	−0.0199 (8)	−0.0102 (7)	−0.0032 (7)
C24	0.0502 (9)	0.0379 (8)	0.0354 (8)	−0.0087 (7)	−0.0091 (7)	−0.0069 (6)
C25	0.0555 (10)	0.0491 (10)	0.0356 (9)	−0.0142 (8)	−0.0053 (7)	0.0016 (7)
C26	0.0500 (10)	0.0489 (10)	0.0469 (10)	−0.0193 (8)	−0.0063 (8)	0.0025 (8)
C27	0.0449 (9)	0.0374 (8)	0.0393 (8)	−0.0107 (7)	−0.0093 (7)	−0.0050 (7)
C28	0.0499 (10)	0.0464 (9)	0.0412 (9)	−0.0119 (8)	−0.0129 (7)	−0.0018 (7)
C29	0.0680 (12)	0.0533 (11)	0.0410 (9)	−0.0129 (9)	−0.0123 (9)	−0.0054 (8)
C30	0.0750 (13)	0.0516 (11)	0.0620 (12)	−0.0168 (10)	−0.0230 (10)	−0.0072 (9)
C31	0.0508 (11)	0.0517 (11)	0.0723 (13)	−0.0131 (9)	−0.0212 (10)	0.0055 (10)
C32	0.0875 (16)	0.0749 (15)	0.0500 (12)	−0.0296 (13)	0.0003 (11)	0.0029 (10)
C33	0.0954 (16)	0.0643 (13)	0.0425 (10)	−0.0284 (12)	−0.0078 (10)	−0.0098 (9)
C34	0.0725 (15)	0.0758 (16)	0.109 (2)	−0.0343 (13)	−0.0311 (14)	0.0193 (14)
N1	0.0679 (11)	0.0688 (12)	0.0599 (11)	−0.0126 (9)	0.0029 (9)	−0.0103 (9)
N2	0.0631 (12)	0.0942 (16)	0.0848 (15)	−0.0095 (11)	−0.0043 (11)	−0.0130 (12)
N3	0.0643 (9)	0.0581 (9)	0.0312 (7)	−0.0139 (8)	−0.0103 (7)	−0.0054 (6)
N4	0.0537 (8)	0.0483 (8)	0.0432 (8)	−0.0204 (7)	−0.0141 (6)	0.0000 (6)
N5	0.0657 (10)	0.0584 (9)	0.0375 (8)	−0.0261 (8)	−0.0145 (7)	0.0008 (7)
N6	0.0615 (9)	0.0488 (8)	0.0349 (7)	−0.0134 (7)	−0.0111 (6)	−0.0074 (6)
O1	0.0662 (9)	0.0856 (10)	0.0476 (8)	−0.0247 (8)	0.0051 (6)	−0.0126 (7)
O2	0.0656 (9)	0.0885 (11)	0.0535 (8)	−0.0167 (8)	−0.0229 (7)	−0.0129 (7)
O3	0.0603 (8)	0.0687 (9)	0.0640 (9)	−0.0187 (7)	0.0032 (7)	0.0018 (7)
O4	0.0865 (11)	0.0710 (10)	0.0846 (11)	−0.0340 (8)	−0.0475 (9)	0.0018 (8)
S1	0.0529 (3)	0.0649 (3)	0.0371 (2)	−0.0147 (2)	−0.00791 (19)	−0.0086 (2)
S2	0.0554 (3)	0.0524 (3)	0.0496 (3)	−0.0189 (2)	−0.0165 (2)	−0.0002 (2)

C1—C2	1.252 (4)	C20—N4	1.451 (2)
C1—H1A	0.9300	C20—H20A	0.9700
C1—H1B	0.9300	C20—H20B	0.9700
C2—C3	1.502 (4)	C21—N5	1.317 (2)
C2—H2	0.9300	C21—C22	1.417 (2)
C3—N1	1.450 (3)	C21—H21	0.9300
C3—H3A	0.9700	C22—C23	1.402 (2)
C3—H3B	0.9700	C22—C27	1.404 (2)
C4—N2	1.317 (3)	C23—C24	1.372 (2)
C4—C5	1.417 (3)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.409 (2)
C5—C6	1.400 (3)	C24—N6	1.448 (2)
C5—C10	1.406 (3)	C25—C26	1.367 (2)
C6—N1	1.364 (3)	C25—H25	0.9300
C6—C7	1.388 (3)	C26—C27	1.398 (2)
C7—C8	1.368 (3)	C26—H26	0.9300
C7—H7	0.9300	C27—N4	1.359 (2)
C8—C9	1.410 (2)	C28—C29	1.376 (3)
C8—H8	0.9300	C28—C33	1.384 (3)
C9—C10	1.365 (3)	C28—S2	1.7592 (18)
C9—N3	1.435 (2)	C29—C30	1.375 (3)
C10—H10	0.9300	C29—H29	0.9300
C11—C16	1.380 (3)	C30—C31	1.382 (3)
C11—C12	1.384 (3)	C30—H30	0.9300
C11—S1	1.762 (2)	C31—C32	1.383 (3)
C12—C13	1.370 (3)	C31—C34	1.503 (3)
C12—H12	0.9300	C32—C33	1.375 (3)
C13—C14	1.383 (4)	C32—H32	0.9300
C13—H13	0.9300	C33—H33	0.9300
C14—C15	1.369 (4)	C34—H34A	0.9600
C14—C17	1.506 (4)	C34—H34B	0.9600
C15—C16	1.390 (4)	C34—H34C	0.9600
C15—H15	0.9300	N1—N2	1.355 (3)
C16—H16	0.9300	N3—S1	1.6219 (16)
C17—H17A	0.9600	N3—H3N	0.7979
C17—H17B	0.9600	N4—N5	1.363 (2)
C17—H17C	0.9600	N6—S2	1.6396 (16)
C18—C19	1.280 (3)	N6—H6N	0.7925
C18—H18A	0.9300	O1—S1	1.4337 (14)
C18—H18B	0.9300	O2—S1	1.4253 (14)
C19—C20	1.493 (3)	O3—S2	1.4283 (15)
C19—H19	0.9300	O4—S2	1.4260 (14)
C2—C1—H1A	120.0	N5—C21—H21	124.3
C2—C1—H1B	120.0	C22—C21—H21	124.3
H1A—C1—H1B	120.0	C23—C22—C27	120.20 (15)
C1—C2—C3	124.6 (4)	C23—C22—C21	135.59 (16)
C1—C2—H2	117.7	C27—C22—C21	104.21 (15)
C3—C2—H2	117.7	C24—C23—C22	117.89 (15)
N1—C3—C2	111.3 (2)	C24—C23—H23	121.1
N1—C3—H3A	109.4	C22—C23—H23	121.1
C2—C3—H3A	109.4	C23—C24—C25	121.15 (15)
N1—C3—H3B	109.4	C23—C24—N6	118.47 (15)
C2—C3—H3B	109.4	C25—C24—N6	120.37 (14)
H3A—C3—H3B	108.0	C26—C25—C24	122.00 (16)
N2—C4—C5	111.7 (2)	C26—C25—H25	119.0
N2—C4—H4	124.2	C24—C25—H25	119.0
C5—C4—H4	124.2	C25—C26—C27	117.11 (16)
C6—C5—C10	119.11 (19)	C25—C26—H26	121.4
C6—C5—C4	104.1 (2)	C27—C26—H26	121.4
C10—C5—C4	136.8 (2)	N4—C27—C26	131.53 (16)
N1—C6—C7	131.43 (19)	N4—C27—C22	106.84 (14)
N1—C6—C5	106.56 (19)	C26—C27—C22	121.63 (15)
C7—C6—C5	122.02 (18)	C29—C28—C33	120.04 (18)
C8—C7—C6	117.81 (18)	C29—C28—S2	120.13 (14)
C8—C7—H7	121.1	C33—C28—S2	119.67 (14)
C6—C7—H7	121.1	C30—C29—C28	119.62 (18)
C7—C8—C9	121.28 (19)	C30—C29—H29	120.2
C7—C8—H8	119.4	C28—C29—H29	120.2
C9—C8—H8	119.4	C29—C30—C31	121.56 (19)
C10—C9—C8	120.84 (17)	C29—C30—H30	119.2
C10—C9—N3	119.27 (16)	C31—C30—H30	119.2
C8—C9—N3	119.79 (17)	C30—C31—C32	117.79 (19)
C9—C10—C5	118.93 (18)	C30—C31—C34	120.7 (2)
C9—C10—H10	120.5	C32—C31—C34	121.5 (2)
C5—C10—H10	120.5	C33—C32—C31	121.6 (2)
C16—C11—C12	120.0 (2)	C33—C32—H32	119.2
C16—C11—S1	120.87 (17)	C31—C32—H32	119.2
C12—C11—S1	119.12 (16)	C32—C33—C28	119.35 (19)
C13—C12—C11	119.9 (2)	C32—C33—H33	120.3
C13—C12—H12	120.0	C28—C33—H33	120.3
C11—C12—H12	120.0	C31—C34—H34A	109.5
C12—C13—C14	121.3 (3)	C31—C34—H34B	109.5
C12—C13—H13	119.4	H34A—C34—H34B	109.5
C14—C13—H13	119.4	C31—C34—H34C	109.5
C15—C14—C13	118.1 (2)	H34A—C34—H34C	109.5
C15—C14—C17	120.2 (3)	H34B—C34—H34C	109.5
C13—C14—C17	121.7 (3)	N2—N1—C6	111.58 (18)
C14—C15—C16	122.1 (2)	N2—N1—C3	120.2 (2)
C14—C15—H15	119.0	C6—N1—C3	128.1 (2)
C16—C15—H15	119.0	C4—N2—N1	106.1 (2)
C11—C16—C15	118.6 (2)	C9—N3—S1	123.01 (12)
C11—C16—H16	120.7	C9—N3—H3N	114.5
C15—C16—H16	120.7	S1—N3—H3N	110.5
C14—C17—H17A	109.5	C27—N4—N5	111.13 (13)
C14—C17—H17B	109.5	C27—N4—C20	128.27 (15)
H17A—C17—H17B	109.5	N5—N4—C20	120.10 (14)
C14—C17—H17C	109.5	C21—N5—N4	106.45 (14)
H17A—C17—H17C	109.5	C24—N6—S2	118.67 (11)
H17B—C17—H17C	109.5	C24—N6—H6N	114.2
C19—C18—H18A	120.0	S2—N6—H6N	108.4
C19—C18—H18B	120.0	O2—S1—O1	118.84 (9)
H18A—C18—H18B	120.0	O2—S1—N3	109.12 (8)
C18—C19—C20	124.7 (2)	O1—S1—N3	104.33 (8)
C18—C19—H19	117.6	O2—S1—C11	108.08 (9)
C20—C19—H19	117.6	O1—S1—C11	107.75 (9)
N4—C20—C19	111.89 (16)	N3—S1—C11	108.31 (9)
N4—C20—H20A	109.2	O4—S2—O3	120.18 (10)
C19—C20—H20A	109.2	O4—S2—N6	105.67 (9)
N4—C20—H20B	109.2	O3—S2—N6	106.80 (8)
C19—C20—H20B	109.2	O4—S2—C28	108.23 (9)
H20A—C20—H20B	107.9	O3—S2—C28	108.43 (9)
N5—C21—C22	111.35 (15)	N6—S2—C28	106.79 (8)
C1—C2—C3—N1	−132.5 (3)	C29—C30—C31—C34	178.9 (2)
N2—C4—C5—C6	1.2 (3)	C30—C31—C32—C33	1.3 (3)
N2—C4—C5—C10	−179.8 (3)	C34—C31—C32—C33	−178.2 (2)
C10—C5—C6—N1	−179.90 (19)	C31—C32—C33—C28	−0.5 (4)
C4—C5—C6—N1	−0.6 (2)	C29—C28—C33—C32	−1.0 (3)
C10—C5—C6—C7	−0.3 (3)	S2—C28—C33—C32	174.52 (18)
C4—C5—C6—C7	178.9 (2)	C7—C6—N1—N2	−179.6 (2)
N1—C6—C7—C8	−179.2 (2)	C5—C6—N1—N2	0.0 (2)
C5—C6—C7—C8	1.3 (3)	C7—C6—N1—C3	4.1 (4)
C6—C7—C8—C9	−0.8 (3)	C5—C6—N1—C3	−176.4 (2)
C7—C8—C9—C10	−0.6 (3)	C2—C3—N1—N2	−100.4 (3)
C7—C8—C9—N3	175.55 (18)	C2—C3—N1—C6	75.7 (3)
C8—C9—C10—C5	1.6 (3)	C5—C4—N2—N1	−1.2 (3)
N3—C9—C10—C5	−174.58 (18)	C6—N1—N2—C4	0.8 (3)
C6—C5—C10—C9	−1.1 (3)	C3—N1—N2—C4	177.5 (2)
C4—C5—C10—C9	179.9 (3)	C10—C9—N3—S1	−124.00 (18)
C16—C11—C12—C13	−1.5 (3)	C8—C9—N3—S1	59.8 (2)
S1—C11—C12—C13	176.62 (18)	C26—C27—N4—N5	−179.05 (18)
C11—C12—C13—C14	−0.9 (4)	C22—C27—N4—N5	1.07 (19)
C12—C13—C14—C15	2.2 (4)	C26—C27—N4—C20	−7.3 (3)
C12—C13—C14—C17	−178.1 (2)	C22—C27—N4—C20	172.87 (17)
C13—C14—C15—C16	−1.0 (4)	C19—C20—N4—C27	−81.8 (2)
C17—C14—C15—C16	179.2 (2)	C19—C20—N4—N5	89.4 (2)
C12—C11—C16—C15	2.6 (3)	C22—C21—N5—N4	1.4 (2)
S1—C11—C16—C15	−175.51 (17)	C27—N4—N5—C21	−1.5 (2)
C14—C15—C16—C11	−1.3 (4)	C20—N4—N5—C21	−174.08 (16)
C18—C19—C20—N4	129.8 (2)	C23—C24—N6—S2	−90.15 (17)
N5—C21—C22—C23	178.45 (19)	C25—C24—N6—S2	90.84 (18)
N5—C21—C22—C27	−0.7 (2)	C9—N3—S1—O2	−56.27 (17)
C27—C22—C23—C24	0.9 (2)	C9—N3—S1—O1	175.74 (14)
C21—C22—C23—C24	−178.2 (2)	C9—N3—S1—C11	61.16 (16)
C22—C23—C24—C25	−1.6 (3)	C16—C11—S1—O2	−4.08 (19)
C22—C23—C24—N6	179.38 (14)	C12—C11—S1—O2	177.84 (16)
C23—C24—C25—C26	0.9 (3)	C16—C11—S1—O1	125.51 (17)
N6—C24—C25—C26	179.90 (16)	C12—C11—S1—O1	−52.57 (18)
C24—C25—C26—C27	0.5 (3)	C16—C11—S1—N3	−122.18 (17)
C25—C26—C27—N4	178.88 (17)	C12—C11—S1—N3	59.74 (18)
C25—C26—C27—C22	−1.3 (3)	C24—N6—S2—O4	−179.54 (13)
C23—C22—C27—N4	−179.55 (15)	C24—N6—S2—O3	51.40 (15)
C21—C22—C27—N4	−0.22 (19)	C24—N6—S2—C28	−64.46 (14)
C23—C22—C27—C26	0.6 (3)	C29—C28—S2—O4	−150.75 (16)
C21—C22—C27—C26	179.88 (16)	C33—C28—S2—O4	33.78 (19)
C33—C28—C29—C30	1.6 (3)	C29—C28—S2—O3	−18.86 (18)
S2—C28—C29—C30	−173.83 (15)	C33—C28—S2—O3	165.67 (17)
C28—C29—C30—C31	−0.8 (3)	C29—C28—S2—N6	95.90 (16)
C29—C30—C31—C32	−0.6 (3)	C33—C28—S2—N6	−79.58 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6N···O1	0.79	2.11	2.900 (2)	176
N3—H3N···N5i	0.80	2.19	2.983 (2)	175
C21—H21···O4ii	0.93	2.49	3.245 (2)	138
C7—H7···O2iii	0.93	2.48	3.358 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6N⋯O1	0.79	2.11	2.900 (2)	176
N3—H3N⋯N5i	0.80	2.19	2.983 (2)	175
C21—H21⋯O4ii	0.93	2.49	3.245 (2)	138
C7—H7⋯O2iii	0.93	2.48	3.358 (2)	158

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