5-Chloro-benzothia-zole-2-spiro-3'-indolin-2'-one.

The title compound, C(14)H(9)ClN(2)OS, crystallizes with two unique mol-ecules, A and B, in the asymmetric unit. The five-membered rings of the benzothia-zole groups in both mol-ecules adopt an envelope conformation [puckering parameters: q(2) = 0.242 (1) Å and ϕ(2) = 217.5 (4)° for A, and q(2) = 0.234 (1) Å and ϕ(2) = 37.7 (4)° for B]. The five-membered rings of the indolinone groups in both mol-ecules are also not planar, with a twisted conformation [puckering parameters are q(2) = 0.112 (2) Å and ϕ(2) = 126.3 (8)° for A, and q(2) = 0.108 (2) Å and ϕ(2) = 306.4 (9)° for B]. In the crystal structure, there are inter-molecular N-H⋯O, N-H⋯S and C-H⋯O hydrogen-bonding inter-actions, forming the layers propagating normal to c.

Related literature

For general background to and applications of 1H-indole-2,3-dione derivatives, see: Alam & Nawwar (2002 ▶); Cho et al. (2008 ▶); Da-Silva et al. (2001 ▶); Dandia et al. (1990 ▶); Hall et al. (2009 ▶); Joshi et al. (1990 ▶); Kumar et al. (2008 ▶); Quenelle et al. (2006 ▶); Vine et al. (2007 ▶, 2009 ▶); Ćaleta et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H9ClN2OS

M = 288.75

Monoclinic,

a = 12.8421 (6) Å

b = 9.1159 (3) Å

c = 22.1553 (9) Å

β = 97.051 (3)°

V = 2574.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.45 mm−1

T = 295 K

0.77 × 0.49 × 0.19 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.723, T max = 0.919

23976 measured reflections

5271 independent reflections

3987 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.080

S = 1.01

5271 reflections

359 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001285/im2170sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001285/im2170Isup2.hkl

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

C14H9ClN2OS	F(000) = 1184
Mr = 288.75	Dx = 1.490 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 33214 reflections
a = 12.8421 (6) Å	θ = 1.6–28.0°
b = 9.1159 (3) Å	µ = 0.45 mm−1
c = 22.1553 (9) Å	T = 295 K
β = 97.051 (3)°	Prism, yellow
V = 2574.1 (2) Å3	0.77 × 0.49 × 0.19 mm
Z = 8

Stoe IPDS 2 diffractometer	5271 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3987 reflections with I > 2σ(I)
plane graphite	Rint = 0.031
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 1.9°
ω scans	h = −14→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→11
Tmin = 0.723, Tmax = 0.919	l = −27→27
23976 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.0864P] where P = (Fo2 + 2Fc2)/3
5271 reflections	(Δ/σ)max < 0.001
359 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	−0.21534 (5)	0.20753 (8)	0.44750 (3)	0.0897 (3)
S1	0.14151 (3)	0.34132 (4)	0.29015 (2)	0.0398 (1)
O1	0.15538 (9)	−0.02243 (11)	0.29802 (5)	0.0468 (4)
N1	0.20968 (12)	0.04018 (14)	0.20602 (7)	0.0459 (5)
N2	−0.02266 (11)	0.17509 (14)	0.25719 (6)	0.0386 (4)
C1	0.17319 (13)	0.13376 (17)	0.15826 (7)	0.0439 (5)
C2	0.09339 (13)	0.22368 (16)	0.17481 (7)	0.0407 (5)
C3	0.04229 (16)	0.32123 (18)	0.13402 (8)	0.0528 (6)
C4	0.0736 (2)	0.3287 (2)	0.07608 (9)	0.0684 (8)
C5	0.1542 (2)	0.2413 (2)	0.06049 (9)	0.0682 (8)
C6	0.20529 (17)	0.1426 (2)	0.10113 (9)	0.0581 (7)
C7	0.15275 (12)	0.05484 (15)	0.25322 (7)	0.0384 (5)
C8	0.08181 (12)	0.19188 (15)	0.24007 (7)	0.0371 (4)
C9	0.04814 (13)	0.31467 (15)	0.34106 (7)	0.0400 (5)
C10	0.04669 (15)	0.3771 (2)	0.39753 (8)	0.0538 (6)
C11	−0.03608 (18)	0.3447 (2)	0.43046 (9)	0.0603 (7)
C12	−0.11329 (15)	0.2499 (2)	0.40578 (8)	0.0541 (6)
C13	−0.11335 (13)	0.18672 (17)	0.34914 (8)	0.0446 (5)
C14	−0.03182 (12)	0.22070 (15)	0.31617 (7)	0.0366 (4)
Cl2	0.71172 (5)	0.55718 (7)	0.05591 (3)	0.0844 (2)
S2	0.35504 (3)	0.42746 (4)	0.21381 (2)	0.0400 (1)
O2	0.34292 (10)	0.79114 (12)	0.20783 (5)	0.0470 (4)
N3	0.29057 (12)	0.72689 (14)	0.30029 (7)	0.0456 (4)
N4	0.52018 (11)	0.59219 (14)	0.24673 (6)	0.0388 (4)
C15	0.32736 (13)	0.63104 (16)	0.34761 (8)	0.0441 (5)
C16	0.29684 (17)	0.6217 (2)	0.40483 (9)	0.0589 (7)
C17	0.3485 (2)	0.5204 (2)	0.44442 (9)	0.0689 (8)
C18	0.4273 (2)	0.4313 (2)	0.42740 (9)	0.0665 (8)
C19	0.45735 (15)	0.44084 (18)	0.36933 (8)	0.0505 (6)
C20	0.40570 (13)	0.54115 (16)	0.32944 (7)	0.0406 (5)
C21	0.34576 (12)	0.71277 (15)	0.25252 (7)	0.0381 (5)
C22	0.41620 (12)	0.57500 (14)	0.26426 (7)	0.0363 (4)
C23	0.44832 (13)	0.45380 (15)	0.16277 (7)	0.0405 (5)
C24	0.44918 (16)	0.3916 (2)	0.10620 (8)	0.0535 (6)
C25	0.53209 (18)	0.4225 (2)	0.07331 (9)	0.0616 (7)
C26	0.60934 (15)	0.5167 (2)	0.09761 (8)	0.0535 (6)
C27	0.60988 (13)	0.58121 (17)	0.15439 (8)	0.0443 (5)
C28	0.52871 (12)	0.54685 (15)	0.18761 (7)	0.0368 (4)
H1A	0.257 (2)	−0.032 (3)	0.2053 (10)	0.081 (7)*
H2A	−0.0558 (16)	0.091 (2)	0.2451 (8)	0.056 (5)*
H3	−0.01150	0.38030	0.14480	0.0630*
H4	0.04000	0.39320	0.04750	0.0820*
H5	0.17450	0.24920	0.02170	0.0820*
H6	0.25940	0.08410	0.09040	0.0700*
H10	0.10020	0.43990	0.41350	0.0650*
H11	−0.03920	0.38640	0.46850	0.0720*
H13	−0.16670	0.12320	0.33360	0.0530*
H3A	0.2402 (19)	0.794 (2)	0.3016 (9)	0.070 (6)*
H4A	0.5540 (16)	0.674 (2)	0.2583 (8)	0.050 (5)*
H16	0.24380	0.68090	0.41650	0.0710*
H17	0.32980	0.51190	0.48350	0.0830*
H18	0.46040	0.36450	0.45510	0.0800*
H19	0.51040	0.38170	0.35770	0.0610*
H24	0.39510	0.32980	0.09020	0.0640*
H25	0.53510	0.37990	0.03540	0.0740*
H27	0.66300	0.64540	0.16960	0.0530*

	U11	U22	U33	U12	U13	U23
Cl1	0.0863 (5)	0.1113 (5)	0.0817 (4)	−0.0106 (4)	0.0518 (4)	0.0006 (3)
S1	0.0346 (2)	0.0328 (2)	0.0528 (2)	−0.0029 (2)	0.0087 (2)	−0.0030 (2)
O1	0.0451 (7)	0.0386 (5)	0.0585 (7)	0.0065 (5)	0.0138 (6)	0.0070 (5)
N1	0.0440 (8)	0.0377 (7)	0.0591 (9)	0.0076 (6)	0.0185 (7)	−0.0010 (6)
N2	0.0303 (7)	0.0369 (6)	0.0492 (8)	−0.0010 (5)	0.0073 (6)	−0.0045 (6)
C1	0.0438 (9)	0.0372 (7)	0.0527 (9)	−0.0045 (7)	0.0143 (7)	−0.0059 (7)
C2	0.0425 (9)	0.0345 (7)	0.0462 (9)	−0.0026 (6)	0.0095 (7)	−0.0031 (6)
C3	0.0586 (12)	0.0463 (9)	0.0536 (10)	0.0033 (8)	0.0075 (9)	0.0017 (7)
C4	0.0886 (18)	0.0634 (12)	0.0530 (11)	−0.0042 (11)	0.0074 (11)	0.0111 (9)
C5	0.0888 (17)	0.0686 (12)	0.0511 (11)	−0.0163 (12)	0.0241 (11)	−0.0036 (9)
C6	0.0643 (13)	0.0544 (10)	0.0604 (11)	−0.0060 (9)	0.0272 (10)	−0.0081 (9)
C7	0.0326 (8)	0.0307 (7)	0.0530 (9)	−0.0008 (6)	0.0092 (7)	−0.0022 (6)
C8	0.0336 (8)	0.0315 (7)	0.0468 (8)	0.0016 (6)	0.0080 (7)	−0.0016 (6)
C9	0.0371 (9)	0.0345 (7)	0.0487 (9)	0.0003 (6)	0.0060 (7)	0.0005 (6)
C10	0.0572 (12)	0.0538 (9)	0.0505 (10)	−0.0064 (9)	0.0072 (8)	−0.0098 (8)
C11	0.0680 (14)	0.0663 (12)	0.0488 (10)	0.0010 (10)	0.0163 (9)	−0.0085 (9)
C12	0.0537 (12)	0.0582 (10)	0.0543 (10)	0.0052 (9)	0.0225 (9)	0.0079 (8)
C13	0.0369 (9)	0.0421 (8)	0.0561 (10)	0.0020 (7)	0.0109 (8)	0.0049 (7)
C14	0.0320 (8)	0.0329 (7)	0.0453 (8)	0.0044 (6)	0.0063 (6)	0.0016 (6)
Cl2	0.0786 (4)	0.1071 (4)	0.0763 (4)	−0.0002 (3)	0.0450 (3)	0.0068 (3)
S2	0.0353 (2)	0.0323 (2)	0.0531 (2)	−0.0031 (2)	0.0084 (2)	−0.0037 (2)
O2	0.0452 (7)	0.0385 (6)	0.0590 (7)	0.0070 (5)	0.0134 (6)	0.0055 (5)
N3	0.0422 (8)	0.0373 (6)	0.0605 (9)	0.0076 (6)	0.0194 (7)	−0.0010 (6)
N4	0.0308 (7)	0.0364 (6)	0.0499 (8)	−0.0023 (5)	0.0081 (6)	−0.0070 (6)
C15	0.0448 (10)	0.0357 (7)	0.0535 (9)	−0.0046 (7)	0.0133 (7)	−0.0041 (7)
C16	0.0678 (13)	0.0531 (10)	0.0604 (11)	−0.0056 (9)	0.0269 (10)	−0.0083 (9)
C17	0.0906 (17)	0.0673 (12)	0.0523 (11)	−0.0088 (12)	0.0234 (11)	0.0001 (9)
C18	0.0848 (17)	0.0620 (11)	0.0517 (11)	0.0016 (11)	0.0048 (10)	0.0102 (9)
C19	0.0544 (11)	0.0429 (8)	0.0534 (10)	0.0025 (7)	0.0037 (8)	0.0004 (7)
C20	0.0404 (9)	0.0350 (7)	0.0470 (9)	−0.0031 (6)	0.0084 (7)	−0.0042 (6)
C21	0.0313 (8)	0.0311 (7)	0.0526 (9)	−0.0008 (6)	0.0080 (7)	−0.0029 (6)
C22	0.0319 (8)	0.0294 (7)	0.0481 (8)	0.0012 (6)	0.0069 (7)	−0.0025 (6)
C23	0.0382 (9)	0.0343 (7)	0.0495 (9)	0.0023 (6)	0.0075 (7)	−0.0002 (6)
C24	0.0593 (12)	0.0509 (9)	0.0502 (9)	−0.0062 (8)	0.0062 (8)	−0.0075 (8)
C25	0.0736 (15)	0.0652 (12)	0.0482 (10)	0.0052 (10)	0.0169 (10)	−0.0062 (9)
C26	0.0538 (11)	0.0563 (10)	0.0538 (10)	0.0076 (8)	0.0204 (9)	0.0078 (8)
C27	0.0360 (9)	0.0429 (8)	0.0551 (10)	0.0027 (7)	0.0102 (7)	0.0051 (7)
C28	0.0324 (8)	0.0312 (7)	0.0469 (8)	0.0044 (6)	0.0054 (6)	0.0013 (6)

Cl1—C12	1.737 (2)	C11—C12	1.377 (3)
Cl2—C26	1.737 (2)	C12—C13	1.381 (2)
S1—C9	1.7609 (17)	C13—C14	1.383 (2)
S1—C8	1.8617 (15)	C3—H3	0.9300
S2—C22	1.8600 (15)	C4—H4	0.9300
S2—C23	1.7619 (17)	C5—H5	0.9300
O1—C7	1.2142 (18)	C6—H6	0.9300
O2—C21	1.2179 (18)	C10—H10	0.9300
N1—C7	1.354 (2)	C11—H11	0.9300
N1—C1	1.395 (2)	C13—H13	0.9300
N2—C14	1.390 (2)	C15—C16	1.375 (3)
N2—C8	1.446 (2)	C15—C20	1.395 (2)
N1—H1A	0.90 (3)	C16—C17	1.385 (3)
N2—H2A	0.901 (19)	C17—C18	1.386 (3)
N3—C15	1.402 (2)	C18—C19	1.391 (3)
N3—C21	1.350 (2)	C19—C20	1.383 (2)
N4—C28	1.391 (2)	C20—C22	1.499 (2)
N4—C22	1.444 (2)	C21—C22	1.551 (2)
N3—H3A	0.89 (2)	C23—C28	1.396 (2)
N4—H4A	0.885 (19)	C23—C24	1.377 (2)
C1—C2	1.396 (2)	C24—C25	1.391 (3)
C1—C6	1.381 (3)	C25—C26	1.371 (3)
C2—C8	1.500 (2)	C26—C27	1.388 (2)
C2—C3	1.376 (2)	C27—C28	1.384 (2)
C3—C4	1.393 (3)	C16—H16	0.9300
C4—C5	1.383 (3)	C17—H17	0.9300
C5—C6	1.381 (3)	C18—H18	0.9300
C7—C8	1.553 (2)	C19—H19	0.9300
C9—C14	1.398 (2)	C24—H24	0.9300
C9—C10	1.377 (2)	C25—H25	0.9300
C10—C11	1.393 (3)	C27—H27	0.9300
Cl1···Cl2i	3.6085 (10)	C13···O2vii	3.206 (2)
Cl2···Cl1ii	3.6085 (10)	C13···C21vii	3.520 (2)
Cl2···H5iii	2.9700	C13···C3vii	3.463 (2)
S1···O1	3.3241 (11)	C14···O1	3.3303 (18)
S1···N1	3.4896 (14)	C15···S1	3.6805 (16)
S1···N2iv	3.5063 (14)	C15···C25ix	3.551 (3)
S1···C15	3.6805 (16)	C16···C25ix	3.510 (3)
S1···S2	3.4836 (6)	C19···C27v	3.414 (2)
S2···N4v	3.5113 (14)	C21···C13iv	3.520 (2)
S2···S1	3.4836 (6)	C25···C16v	3.510 (3)
S2···O2	3.3208 (12)	C25···C15v	3.551 (3)
S2···N3	3.4923 (14)	C25···C25iii	3.546 (3)
S2···C1	3.6649 (16)	C27···C19ix	3.414 (2)
S1···H2Aiv	2.606 (19)	C27···C7ix	3.465 (2)
S1···H27v	3.1200	C27···O1ix	3.211 (2)
S2···H13iv	3.0800	C28···O2	3.3339 (19)
S2···H4Av	2.628 (19)	C6···H24	3.0100
O1···N2	2.9632 (18)	C7···H3Avi	2.787 (19)
O1···N3vi	2.8666 (18)	C7···H27v	2.8700
O1···S1	3.3241 (11)	C16···H10	3.0500
O1···C3vii	3.418 (2)	C21···H1Aviii	2.74 (3)
O1···C14	3.3303 (18)	C21···H13iv	2.9200
O1···C27v	3.211 (2)	C23···H4Av	3.095 (18)
O2···C28	3.3339 (19)	C25···H25iii	3.0500
O2···N1viii	2.8402 (18)	H1A···C21vi	2.74 (3)
O2···N4	2.9550 (18)	H1A···O2vi	1.95 (3)
O2···S2	3.3208 (12)	H2A···S1vii	2.606 (19)
O2···C13iv	3.206 (2)	H2A···H13	2.5800
O1···H3Avi	1.99 (2)	H3···O1iv	2.5300
O1···H27v	2.8100	H3A···C7viii	2.787 (19)
O1···H3vii	2.5300	H3A···O1viii	1.99 (2)
O2···H1Aviii	1.95 (3)	H4A···S2ix	2.628 (19)
O2···H13iv	2.7900	H4A···C23ix	3.095 (18)
O2···H19ix	2.6500	H4A···H27	2.5600
N1···S1	3.4896 (14)	H5···Cl2iii	2.9700
N1···O2vi	2.8402 (18)	H10···C16	3.0500
N2···S1vii	3.5063 (14)	H13···O2vii	2.7900
N2···O1	2.9632 (18)	H13···C21vii	2.9200
N3···O1viii	2.8666 (18)	H13···S2vii	3.0800
N3···S2	3.4923 (14)	H13···H2A	2.5800
N4···O2	2.9550 (18)	H19···O2v	2.6500
N4···S2ix	3.5113 (14)	H24···C6	3.0100
C1···S2	3.6649 (16)	H25···C25iii	3.0500
C3···C13iv	3.463 (2)	H27···H4A	2.5600
C3···O1iv	3.418 (2)	H27···S1ix	3.1200
C6···C11vii	3.495 (3)	H27···O1ix	2.8100
C7···C27v	3.465 (2)	H27···C7ix	2.8700
C11···C6iv	3.495 (3)
C8—S1—C9	91.02 (7)	C5—C6—H6	121.00
C22—S2—C23	90.97 (7)	C9—C10—H10	121.00
C1—N1—C7	111.26 (14)	C11—C10—H10	120.00
C8—N2—C14	113.78 (13)	C10—C11—H11	121.00
C7—N1—H1A	121.2 (15)	C12—C11—H11	120.00
C1—N1—H1A	126.9 (14)	C12—C13—H13	121.00
C8—N2—H2A	115.6 (13)	C14—C13—H13	121.00
C14—N2—H2A	116.3 (12)	C16—C15—C20	121.82 (16)
C15—N3—C21	111.45 (14)	N3—C15—C16	128.34 (16)
C22—N4—C28	113.79 (13)	N3—C15—C20	109.83 (15)
C21—N3—H3A	122.9 (13)	C15—C16—C17	117.16 (19)
C15—N3—H3A	125.6 (13)	C16—C17—C18	121.83 (19)
C28—N4—H4A	115.5 (12)	C17—C18—C19	120.67 (18)
C22—N4—H4A	116.8 (13)	C18—C19—C20	117.82 (17)
N1—C1—C2	110.43 (14)	C15—C20—C19	120.69 (15)
N1—C1—C6	128.38 (16)	C15—C20—C22	108.09 (13)
C2—C1—C6	121.19 (15)	C19—C20—C22	131.22 (15)
C3—C2—C8	131.49 (15)	O2—C21—N3	127.96 (14)
C1—C2—C8	107.61 (13)	O2—C21—C22	124.75 (14)
C1—C2—C3	120.89 (15)	N3—C21—C22	107.29 (12)
C2—C3—C4	117.94 (18)	S2—C22—C20	110.41 (10)
C3—C4—C5	120.76 (18)	S2—C22—C21	106.87 (10)
C4—C5—C6	121.53 (19)	S2—C22—N4	104.66 (10)
C1—C6—C5	117.68 (19)	C20—C22—C21	102.05 (12)
O1—C7—C8	125.24 (14)	N4—C22—C20	118.49 (13)
O1—C7—N1	127.63 (14)	N4—C22—C21	113.99 (12)
N1—C7—C8	107.13 (12)	S2—C23—C28	110.98 (11)
S1—C8—C2	110.54 (10)	C24—C23—C28	121.39 (16)
N2—C8—C2	118.57 (13)	S2—C23—C24	127.60 (13)
N2—C8—C7	114.05 (12)	C23—C24—C25	119.06 (17)
S1—C8—N2	104.39 (10)	C24—C25—C26	118.99 (18)
C2—C8—C7	102.19 (12)	Cl2—C26—C25	118.86 (15)
S1—C8—C7	106.72 (10)	Cl2—C26—C27	118.18 (14)
S1—C9—C14	110.91 (11)	C25—C26—C27	122.96 (18)
C10—C9—C14	121.38 (16)	C26—C27—C28	117.77 (15)
S1—C9—C10	127.68 (13)	N4—C28—C27	125.83 (14)
C9—C10—C11	119.00 (17)	C23—C28—C27	119.79 (14)
C10—C11—C12	118.93 (18)	N4—C28—C23	114.33 (14)
C11—C12—C13	122.87 (18)	C15—C16—H16	121.00
Cl1—C12—C11	118.80 (15)	C17—C16—H16	121.00
Cl1—C12—C13	118.33 (14)	C16—C17—H17	119.00
C12—C13—C14	118.07 (15)	C18—C17—H17	119.00
N2—C14—C13	125.90 (14)	C17—C18—H18	120.00
C9—C14—C13	119.73 (14)	C19—C18—H18	120.00
N2—C14—C9	114.29 (14)	C18—C19—H19	121.00
C4—C3—H3	121.00	C20—C19—H19	121.00
C2—C3—H3	121.00	C23—C24—H24	120.00
C3—C4—H4	120.00	C25—C24—H24	120.00
C5—C4—H4	120.00	C24—C25—H25	121.00
C6—C5—H5	119.00	C26—C25—H25	121.00
C4—C5—H5	119.00	C26—C27—H27	121.00
C1—C6—H6	121.00	C28—C27—H27	121.00
C9—S1—C8—C7	−101.67 (11)	O1—C7—C8—S1	75.43 (17)
C8—S1—C9—C10	171.57 (16)	C10—C9—C14—N2	175.71 (15)
C8—S1—C9—C14	−10.32 (12)	C14—C9—C10—C11	0.4 (3)
C9—S1—C8—N2	19.41 (10)	C10—C9—C14—C13	−1.3 (2)
C9—S1—C8—C2	147.97 (11)	S1—C9—C14—C13	−179.58 (12)
C23—S2—C22—C21	102.41 (11)	S1—C9—C10—C11	178.36 (14)
C23—S2—C22—C20	−147.38 (11)	S1—C9—C14—N2	−2.55 (16)
C22—S2—C23—C28	9.92 (12)	C9—C10—C11—C12	0.7 (3)
C23—S2—C22—N4	−18.82 (10)	C10—C11—C12—Cl1	179.01 (15)
C22—S2—C23—C24	−172.01 (16)	C10—C11—C12—C13	−1.0 (3)
C1—N1—C7—O1	169.93 (15)	C11—C12—C13—C14	0.1 (3)
C1—N1—C7—C8	−10.37 (17)	Cl1—C12—C13—C14	−179.91 (13)
C7—N1—C1—C6	−174.55 (17)	C12—C13—C14—C9	1.0 (2)
C7—N1—C1—C2	4.51 (19)	C12—C13—C14—N2	−175.62 (15)
C8—N2—C14—C9	19.25 (18)	C16—C15—C20—C19	−1.5 (3)
C8—N2—C14—C13	−163.92 (14)	C16—C15—C20—C22	177.60 (16)
C14—N2—C8—S1	−25.03 (14)	N3—C15—C20—C19	177.41 (15)
C14—N2—C8—C2	−148.54 (13)	N3—C15—C20—C22	−3.54 (18)
C14—N2—C8—C7	91.06 (15)	C20—C15—C16—C17	1.0 (3)
C15—N3—C21—C22	10.02 (17)	N3—C15—C16—C17	−177.60 (18)
C21—N3—C15—C16	174.40 (17)	C15—C16—C17—C18	−0.3 (3)
C15—N3—C21—O2	−169.98 (16)	C16—C17—C18—C19	0.0 (3)
C21—N3—C15—C20	−4.37 (19)	C17—C18—C19—C20	−0.3 (3)
C22—N4—C28—C23	−18.74 (18)	C18—C19—C20—C15	1.1 (3)
C28—N4—C22—C20	147.82 (13)	C18—C19—C20—C22	−177.75 (17)
C22—N4—C28—C27	164.02 (14)	C15—C20—C22—S2	−104.54 (13)
C28—N4—C22—C21	−92.09 (15)	C15—C20—C22—C21	8.79 (16)
C28—N4—C22—S2	24.31 (14)	C19—C20—C22—S2	74.4 (2)
N1—C1—C6—C5	177.63 (18)	C15—C20—C22—N4	134.86 (14)
N1—C1—C2—C3	−177.35 (15)	C19—C20—C22—N4	−46.2 (2)
C2—C1—C6—C5	−1.3 (3)	C19—C20—C22—C21	−172.30 (17)
C6—C1—C2—C8	−177.18 (16)	O2—C21—C22—C20	168.65 (15)
N1—C1—C2—C8	3.69 (18)	O2—C21—C22—N4	39.7 (2)
C6—C1—C2—C3	1.8 (3)	N3—C21—C22—C20	−11.35 (16)
C1—C2—C8—S1	104.15 (13)	N3—C21—C22—S2	104.59 (12)
C3—C2—C8—N2	45.7 (2)	N3—C21—C22—N4	−140.30 (13)
C3—C2—C8—C7	172.06 (17)	O2—C21—C22—S2	−75.41 (17)
C1—C2—C8—N2	−135.45 (14)	C28—C23—C24—C25	0.0 (3)
C1—C2—C8—C7	−9.13 (16)	S2—C23—C28—N4	2.57 (16)
C3—C2—C8—S1	−74.7 (2)	C24—C23—C28—N4	−175.64 (15)
C1—C2—C3—C4	−0.8 (3)	C24—C23—C28—C27	1.8 (2)
C8—C2—C3—C4	177.86 (17)	S2—C23—C28—C27	180.00 (12)
C2—C3—C4—C5	−0.5 (3)	S2—C23—C24—C25	−177.89 (14)
C3—C4—C5—C6	0.9 (3)	C23—C24—C25—C26	−1.5 (3)
C4—C5—C6—C1	0.0 (3)	C24—C25—C26—C27	1.2 (3)
N1—C7—C8—C2	11.79 (16)	C24—C25—C26—Cl2	−179.04 (15)
N1—C7—C8—N2	140.99 (13)	Cl2—C26—C27—C28	−179.19 (13)
N1—C7—C8—S1	−104.29 (12)	C25—C26—C27—C28	0.5 (3)
O1—C7—C8—C2	−168.49 (15)	C26—C27—C28—C23	−2.0 (2)
O1—C7—C8—N2	−39.3 (2)	C26—C27—C28—N4	175.09 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2vi	0.90 (3)	1.95 (3)	2.840 (2)	171 (2)
N2—H2A···S1vii	0.90 (2)	2.61 (2)	3.506 (1)	177 (2)
N3—H3A···O1viii	0.89 (2)	1.99 (2)	2.867 (2)	166 (2)
N4—H4A···S2ix	0.89 (2)	2.63 (2)	3.511 (1)	176 (2)
C3—H3···O1iv	0.93	2.53	3.418 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.90 (3)	1.95 (3)	2.840 (2)	171 (2)
N2—H2A⋯S1ii	0.90 (2)	2.61 (2)	3.506 (1)	177 (2)
N3—H3A⋯O1iii	0.89 (2)	1.99 (2)	2.867 (2)	166 (2)
N4—H4A⋯S2iv	0.89 (2)	2.63 (2)	3.511 (1)	176 (2)
C3—H3⋯O1v	0.93	2.53	3.418 (2)	161

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