6-[3-(p-Tolyl-sulfonyl-amino)-prop-yl]diquino-thia-zine.

In the title mol-ecule {systematic name: N-[3-(diquino[3,2-b;2',3'-e][1,4]thia-zin-6-yl)prop-yl]-4-methyl-benzene-sulfon-amide}, C28H24N4O2S2, the penta-cyclic system is relatively planar [maximum deviation from the mean plane = 0.242 (1) Å]. The dihedral angle between two quinoline ring systems is 8.23 (2)° and that between the two halves of the 1,4-thia-zine ring is 5.68 (3)°. The conformation adopted by the 3-(p-tolyl-sulfonyl-amino)-propyl substituent allows for the formation of an intra-molecular N-H⋯N hydrogen bond and places the benzene ring of this substituent above one of the quinoline fragments of the penta-cyclic system. In the crystal, mol-ecules are arranged via π-π stacking inter-actions into (0-11) layers [centroid-centroid distances = 3.981 (1)-4.320 (1) Å for the rings in the penta-cyclic system and 3.645 (1) Å for the tolyl benzene rings]. In addition, mol-ecules are involved in weak C-H⋯O, which connect the layers, and C-H⋯S hydrogen bonds. The title compound shows promising anti-cancer activity against renal cancer cell line UO-31.

Related literature

For the structures of hetero­penta­cenes, see: Anthony (2006 ▶); Isaia et al. (2009 ▶); Yoshida et al. (1994 ▶). For recent literature on the biological activity of pheno­thia­zines, see: Aaron et al. (2009 ▶); Pluta et al. (2011 ▶). For the synthesis and biological activity of 6-substituted diquino­thia­zines, see: Nowak et al. (2007 ▶); Jeleń & Pluta (2009 ▶); Pluta et al. (2010 ▶). For crystal structures of pheno­thia­zines, see: Chu (1988 ▶). For information on aza­pheno­thia­zines, their nomenclature and synthesis, see: Pluta et al. (2009 ▶). For hetero­penta­cenes with quinoline moieties containing nitro­gen, sulfur, oxygen and selenium, see: Nowak et al. (2002 ▶); Pluta et al. (2000 ▶).

Experimental

Crystal data

C28H24N4O2S2

M = 512.63

Triclinic,

a = 9.3986 (3) Å

b = 10.3793 (3) Å

c = 12.6207 (3) Å

α = 80.735 (2)°

β = 81.959 (2)°

γ = 77.999 (2)°

V = 1181.30 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.39 × 0.34 × 0.23 mm

Data collection

Agilent SuperNova Dual (Cu at zero, Eos) diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶) and Clark & Reid (1995 ▶)] T min = 0.937, T max = 0.965

24091 measured reflections

7396 independent reflections

6770 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.093

S = 1.04

7396 reflections

329 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013950/gk2566sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013950/gk2566Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013950/gk2566Isup3.cml

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

C28H24N4O2S2	Z = 2
Mr = 512.63	F(000) = 536
Triclinic, P1	Dx = 1.441 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3986 (3) Å	Cell parameters from 16661 reflections
b = 10.3793 (3) Å	θ = 3.3–32.2°
c = 12.6207 (3) Å	µ = 0.26 mm−1
α = 80.735 (2)°	T = 100 K
β = 81.959 (2)°	Block, yellow
γ = 77.999 (2)°	0.39 × 0.34 × 0.23 mm
V = 1181.30 (6) Å3

Agilent SuperNova Dual (Cu at zero, Eos) diffractometer	7396 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	6770 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.015
Detector resolution: 16.2974 pixels mm-1	θmax = 31.0°, θmin = 3.3°
ω scans	h = −13→13
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012) and Clark & Reid (1995)]	k = −15→15
Tmin = 0.937, Tmax = 0.965	l = −18→18
24091 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) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.437P] where P = (Fo2 + 2Fc2)/3
7396 reflections	(Δ/σ)max = 0.002
329 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.40 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
C1	0.49893 (13)	1.01160 (10)	0.71760 (9)	0.0272 (2)
H1	0.4759	1.0911	0.6691	0.033*
C2	0.55824 (14)	1.01426 (11)	0.81047 (10)	0.0316 (2)
H2	0.5750	1.0958	0.8266	0.038*
C3	0.59430 (13)	0.89597 (11)	0.88211 (10)	0.0284 (2)
H3	0.6354	0.8987	0.9462	0.034*
C4	0.57070 (11)	0.77664 (10)	0.86036 (8)	0.02243 (18)
H4	0.5972	0.6975	0.9085	0.027*
C4A	0.50694 (10)	0.77236 (9)	0.76632 (8)	0.01797 (16)
N5	0.47657 (8)	0.65388 (8)	0.75030 (6)	0.01707 (14)
C5A	0.41609 (9)	0.64626 (9)	0.66422 (7)	0.01604 (16)
N6	0.38838 (9)	0.52185 (8)	0.65386 (7)	0.01928 (15)
C6A	0.31384 (10)	0.49652 (9)	0.57300 (8)	0.01871 (17)
N7	0.28831 (10)	0.37503 (8)	0.58262 (7)	0.02115 (16)
C7A	0.21392 (11)	0.34230 (10)	0.50797 (8)	0.02097 (18)
C8	0.18288 (13)	0.21269 (10)	0.52247 (9)	0.0270 (2)
H8	0.2161	0.1500	0.5816	0.032*
C9	0.10458 (14)	0.17702 (11)	0.45114 (10)	0.0307 (2)
H9	0.0841	0.0897	0.4613	0.037*
C10	0.05463 (14)	0.26913 (12)	0.36322 (9)	0.0301 (2)
H10	−0.0011	0.2440	0.3154	0.036*
C11	0.08566 (12)	0.39472 (11)	0.34607 (9)	0.0264 (2)
H11	0.0536	0.4555	0.2856	0.032*
C11A	0.16556 (11)	0.43355 (10)	0.41872 (8)	0.02102 (18)
C12	0.19770 (11)	0.56268 (10)	0.40906 (8)	0.02207 (18)
H12	0.1697	0.6267	0.3492	0.026*
C12A	0.26858 (11)	0.59588 (9)	0.48515 (8)	0.01975 (17)
S13	0.30095 (3)	0.75808 (3)	0.46855 (2)	0.02831 (7)
C13A	0.37960 (10)	0.76078 (9)	0.58521 (7)	0.01722 (16)
C14	0.40755 (10)	0.87994 (9)	0.60157 (8)	0.01950 (17)
H14	0.3834	0.9565	0.5503	0.023*
C14A	0.47201 (11)	0.89058 (9)	0.69388 (8)	0.01988 (17)
C15	0.43639 (12)	0.40812 (9)	0.73615 (8)	0.02281 (19)
H15A	0.5134	0.4294	0.7728	0.027*
H15B	0.4803	0.3295	0.6994	0.027*
C16	0.31325 (14)	0.37268 (10)	0.82111 (9)	0.0278 (2)
H16A	0.2456	0.3360	0.7859	0.033*
H16B	0.3561	0.3015	0.8761	0.033*
C17	0.22489 (12)	0.48651 (11)	0.87824 (8)	0.02409 (19)
H17A	0.1897	0.5623	0.8239	0.029*
H17B	0.1383	0.4578	0.9222	0.029*
S19	0.22842 (3)	0.62938 (3)	1.034198 (18)	0.02204 (6)
O20	0.33837 (9)	0.65975 (8)	1.08936 (6)	0.02723 (16)
O21	0.11287 (9)	0.56819 (11)	1.09446 (7)	0.0372 (2)
C22	0.14699 (11)	0.77850 (11)	0.95968 (8)	0.02354 (19)
C23	0.01915 (12)	0.78269 (14)	0.91344 (9)	0.0304 (2)
H23	−0.0268	0.7075	0.9245	0.036*
C24	−0.03909 (13)	0.89937 (15)	0.85096 (9)	0.0369 (3)
H24	−0.1254	0.9030	0.8185	0.044*
C25	0.02520 (14)	1.01107 (14)	0.83459 (9)	0.0362 (3)
C26	0.15136 (14)	1.00516 (13)	0.88263 (9)	0.0333 (3)
H26	0.1959	1.0811	0.8730	0.040*
C27	0.21278 (12)	0.88873 (11)	0.94467 (9)	0.0267 (2)
H27	0.2995	0.8849	0.9766	0.032*
C28	−0.04257 (19)	1.13661 (16)	0.76733 (10)	0.0514 (4)
H28A	−0.0395	1.1199	0.6927	0.077*
H28B	0.0122	1.2069	0.7687	0.077*
H28C	−0.1445	1.1646	0.7969	0.077*
N18	0.31353 (9)	0.52970 (8)	0.94864 (7)	0.01995 (15)
H18	0.3886 (16)	0.5609 (14)	0.9126 (12)	0.024*

	U11	U22	U33	U12	U13	U23
C1	0.0354 (5)	0.0178 (4)	0.0308 (5)	−0.0121 (4)	−0.0060 (4)	0.0007 (4)
C2	0.0432 (6)	0.0208 (5)	0.0365 (6)	−0.0153 (4)	−0.0099 (5)	−0.0036 (4)
C3	0.0364 (6)	0.0247 (5)	0.0287 (5)	−0.0130 (4)	−0.0091 (4)	−0.0036 (4)
C4	0.0260 (4)	0.0203 (4)	0.0232 (4)	−0.0087 (4)	−0.0054 (4)	−0.0016 (3)
C4A	0.0181 (4)	0.0161 (4)	0.0200 (4)	−0.0056 (3)	−0.0007 (3)	−0.0017 (3)
N5	0.0176 (3)	0.0150 (3)	0.0190 (3)	−0.0036 (3)	−0.0033 (3)	−0.0016 (3)
C5A	0.0156 (4)	0.0133 (4)	0.0186 (4)	−0.0022 (3)	−0.0027 (3)	−0.0006 (3)
N6	0.0259 (4)	0.0122 (3)	0.0209 (4)	−0.0029 (3)	−0.0114 (3)	0.0011 (3)
C6A	0.0212 (4)	0.0156 (4)	0.0197 (4)	−0.0018 (3)	−0.0078 (3)	−0.0010 (3)
N7	0.0264 (4)	0.0150 (3)	0.0237 (4)	−0.0026 (3)	−0.0111 (3)	−0.0019 (3)
C7A	0.0241 (4)	0.0182 (4)	0.0219 (4)	−0.0021 (3)	−0.0083 (3)	−0.0040 (3)
C8	0.0350 (5)	0.0179 (4)	0.0307 (5)	−0.0035 (4)	−0.0140 (4)	−0.0039 (4)
C9	0.0391 (6)	0.0228 (5)	0.0351 (6)	−0.0074 (4)	−0.0132 (5)	−0.0083 (4)
C10	0.0360 (6)	0.0325 (6)	0.0268 (5)	−0.0084 (5)	−0.0110 (4)	−0.0098 (4)
C11	0.0310 (5)	0.0312 (5)	0.0197 (4)	−0.0075 (4)	−0.0088 (4)	−0.0040 (4)
C11A	0.0230 (4)	0.0231 (4)	0.0180 (4)	−0.0041 (3)	−0.0055 (3)	−0.0032 (3)
C12	0.0249 (4)	0.0227 (4)	0.0187 (4)	−0.0048 (4)	−0.0076 (3)	0.0018 (3)
C12A	0.0226 (4)	0.0168 (4)	0.0195 (4)	−0.0034 (3)	−0.0065 (3)	0.0017 (3)
S13	0.04278 (16)	0.01844 (12)	0.02660 (13)	−0.01033 (10)	−0.01874 (11)	0.00722 (9)
C13A	0.0170 (4)	0.0157 (4)	0.0179 (4)	−0.0031 (3)	−0.0020 (3)	0.0011 (3)
C14	0.0209 (4)	0.0157 (4)	0.0208 (4)	−0.0053 (3)	−0.0008 (3)	0.0020 (3)
C14A	0.0217 (4)	0.0166 (4)	0.0217 (4)	−0.0074 (3)	−0.0005 (3)	−0.0005 (3)
C15	0.0339 (5)	0.0117 (4)	0.0240 (4)	−0.0009 (3)	−0.0167 (4)	0.0013 (3)
C16	0.0453 (6)	0.0167 (4)	0.0254 (5)	−0.0128 (4)	−0.0162 (4)	0.0049 (4)
C17	0.0271 (5)	0.0251 (5)	0.0229 (4)	−0.0127 (4)	−0.0096 (4)	0.0044 (4)
S19	0.01835 (11)	0.03176 (13)	0.01380 (10)	−0.00181 (9)	−0.00435 (8)	0.00184 (8)
O20	0.0256 (4)	0.0342 (4)	0.0215 (3)	0.0027 (3)	−0.0122 (3)	−0.0053 (3)
O21	0.0277 (4)	0.0619 (6)	0.0180 (3)	−0.0125 (4)	−0.0001 (3)	0.0093 (4)
C22	0.0180 (4)	0.0338 (5)	0.0146 (4)	0.0056 (4)	−0.0031 (3)	−0.0036 (4)
C23	0.0186 (4)	0.0486 (7)	0.0199 (4)	0.0054 (4)	−0.0045 (4)	−0.0059 (4)
C24	0.0257 (5)	0.0564 (8)	0.0206 (5)	0.0174 (5)	−0.0085 (4)	−0.0093 (5)
C25	0.0381 (6)	0.0426 (7)	0.0156 (4)	0.0209 (5)	−0.0028 (4)	−0.0052 (4)
C26	0.0376 (6)	0.0310 (6)	0.0231 (5)	0.0113 (5)	−0.0010 (4)	−0.0044 (4)
C27	0.0252 (5)	0.0290 (5)	0.0222 (4)	0.0066 (4)	−0.0048 (4)	−0.0055 (4)
C28	0.0593 (9)	0.0539 (9)	0.0213 (5)	0.0314 (7)	−0.0067 (5)	−0.0004 (5)
N18	0.0201 (4)	0.0214 (4)	0.0187 (4)	−0.0059 (3)	−0.0051 (3)	0.0011 (3)

C1—C2	1.3730 (16)	S13—C13A	1.7440 (10)
C1—C14A	1.4163 (13)	C13A—C14	1.3689 (13)
C1—H1	0.9500	C14—C14A	1.4152 (14)
C2—C3	1.4124 (16)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.5256 (17)
C3—C4	1.3782 (14)	C15—H15A	0.9900
C3—H3	0.9500	C15—H15B	0.9900
C4—C4A	1.4130 (13)	C16—C17	1.5179 (16)
C4—H4	0.9500	C16—H16A	0.9900
C4A—N5	1.3699 (11)	C16—H16B	0.9900
C4A—C14A	1.4158 (13)	C17—N18	1.4748 (13)
N5—C5A	1.3149 (12)	C17—H17A	0.9900
C5A—N6	1.3986 (11)	C17—H17B	0.9900
C5A—C13A	1.4384 (12)	S19—O20	1.4351 (8)
N6—C6A	1.4016 (12)	S19—O21	1.4357 (9)
N6—C15	1.4800 (12)	S19—N18	1.6279 (9)
C6A—N7	1.3156 (12)	S19—C22	1.7623 (11)
C6A—C12A	1.4335 (13)	C22—C27	1.3852 (17)
N7—C7A	1.3704 (12)	C22—C23	1.3974 (14)
C7A—C11A	1.4118 (14)	C23—C24	1.3877 (17)
C7A—C8	1.4133 (14)	C23—H23	0.9500
C8—C9	1.3765 (15)	C24—C25	1.390 (2)
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.4082 (17)	C25—C26	1.3914 (19)
C9—H9	0.9500	C25—C28	1.5080 (17)
C10—C11	1.3714 (16)	C26—C27	1.3923 (15)
C10—H10	0.9500	C26—H26	0.9500
C11—C11A	1.4158 (13)	C27—H27	0.9500
C11—H11	0.9500	C28—H28A	0.9800
C11A—C12	1.4170 (14)	C28—H28B	0.9800
C12—C12A	1.3660 (13)	C28—H28C	0.9800
C12—H12	0.9500	N18—H18	0.876 (15)
C12A—S13	1.7471 (10)
C2—C1—C14A	120.16 (10)	C14A—C14—H14	119.6
C2—C1—H1	119.9	C14—C14A—C4A	116.65 (8)
C14A—C1—H1	119.9	C14—C14A—C1	123.70 (9)
C1—C2—C3	120.11 (10)	C4A—C14A—C1	119.63 (9)
C1—C2—H2	119.9	N6—C15—C16	113.75 (9)
C3—C2—H2	119.9	N6—C15—H15A	108.8
C4—C3—C2	120.90 (10)	C16—C15—H15A	108.8
C4—C3—H3	119.6	N6—C15—H15B	108.8
C2—C3—H3	119.6	C16—C15—H15B	108.8
C3—C4—C4A	119.82 (10)	H15A—C15—H15B	107.7
C3—C4—H4	120.1	C17—C16—C15	115.55 (8)
C4A—C4—H4	120.1	C17—C16—H16A	108.4
N5—C4A—C4	118.46 (8)	C15—C16—H16A	108.4
N5—C4A—C14A	122.16 (9)	C17—C16—H16B	108.4
C4—C4A—C14A	119.35 (8)	C15—C16—H16B	108.4
C5A—N5—C4A	120.21 (8)	H16A—C16—H16B	107.5
N5—C5A—N6	116.71 (8)	N18—C17—C16	111.15 (9)
N5—C5A—C13A	121.40 (8)	N18—C17—H17A	109.4
N6—C5A—C13A	121.88 (8)	C16—C17—H17A	109.4
C5A—N6—C6A	125.03 (8)	N18—C17—H17B	109.4
C5A—N6—C15	118.16 (8)	C16—C17—H17B	109.4
C6A—N6—C15	116.78 (7)	H17A—C17—H17B	108.0
N7—C6A—N6	115.61 (8)	O20—S19—O21	119.96 (5)
N7—C6A—C12A	121.93 (8)	O20—S19—N18	106.67 (5)
N6—C6A—C12A	122.46 (8)	O21—S19—N18	106.71 (6)
C6A—N7—C7A	119.45 (8)	O20—S19—C22	107.48 (5)
N7—C7A—C11A	122.50 (9)	O21—S19—C22	107.68 (5)
N7—C7A—C8	118.34 (9)	N18—S19—C22	107.82 (4)
C11A—C7A—C8	119.15 (9)	C27—C22—C23	120.77 (10)
C9—C8—C7A	120.19 (10)	C27—C22—S19	119.75 (8)
C9—C8—H8	119.9	C23—C22—S19	119.44 (9)
C7A—C8—H8	119.9	C24—C23—C22	118.36 (13)
C8—C9—C10	120.41 (10)	C24—C23—H23	120.8
C8—C9—H9	119.8	C22—C23—H23	120.8
C10—C9—H9	119.8	C23—C24—C25	121.87 (11)
C11—C10—C9	120.59 (10)	C23—C24—H24	119.1
C11—C10—H10	119.7	C25—C24—H24	119.1
C9—C10—H10	119.7	C24—C25—C26	118.76 (11)
C10—C11—C11A	119.87 (10)	C24—C25—C28	120.26 (13)
C10—C11—H11	120.1	C26—C25—C28	120.97 (15)
C11A—C11—H11	120.1	C25—C26—C27	120.43 (13)
C7A—C11A—C11	119.76 (9)	C25—C26—H26	119.8
C7A—C11A—C12	116.77 (9)	C27—C26—H26	119.8
C11—C11A—C12	123.45 (9)	C22—C27—C26	119.80 (11)
C12A—C12—C11A	120.52 (9)	C22—C27—H27	120.1
C12A—C12—H12	119.7	C26—C27—H27	120.1
C11A—C12—H12	119.7	C25—C28—H28A	109.5
C12—C12A—C6A	118.79 (9)	C25—C28—H28B	109.5
C12—C12A—S13	117.62 (7)	H28A—C28—H28B	109.5
C6A—C12A—S13	123.58 (7)	C25—C28—H28C	109.5
C13A—S13—C12A	102.57 (4)	H28A—C28—H28C	109.5
C14—C13A—C5A	118.69 (8)	H28B—C28—H28C	109.5
C14—C13A—S13	117.28 (7)	C17—N18—S19	117.64 (7)
C5A—C13A—S13	124.04 (7)	C17—N18—H18	112.7 (9)
C13A—C14—C14A	120.87 (9)	S19—N18—H18	109.9 (9)
C13A—C14—H14	119.6
C14A—C1—C2—C3	0.77 (19)	C6A—C12A—S13—C13A	−4.78 (10)
C1—C2—C3—C4	−0.06 (19)	N5—C5A—C13A—C14	−0.73 (14)
C2—C3—C4—C4A	−1.26 (17)	N6—C5A—C13A—C14	178.87 (8)
C3—C4—C4A—N5	−176.04 (10)	N5—C5A—C13A—S13	179.35 (7)
C3—C4—C4A—C14A	1.85 (15)	N6—C5A—C13A—S13	−1.05 (13)
C4—C4A—N5—C5A	179.42 (9)	C12A—S13—C13A—C14	−174.70 (8)
C14A—C4A—N5—C5A	1.59 (14)	C12A—S13—C13A—C5A	5.22 (9)
C4A—N5—C5A—N6	−179.91 (8)	C5A—C13A—C14—C14A	0.45 (14)
C4A—N5—C5A—C13A	−0.29 (13)	S13—C13A—C14—C14A	−179.63 (7)
N5—C5A—N6—C6A	174.38 (9)	C13A—C14—C14A—C4A	0.75 (14)
C13A—C5A—N6—C6A	−5.24 (15)	C13A—C14—C14A—C1	−177.64 (10)
N5—C5A—N6—C15	−3.43 (13)	N5—C4A—C14A—C14	−1.80 (14)
C13A—C5A—N6—C15	176.96 (9)	C4—C4A—C14A—C14	−179.61 (9)
C5A—N6—C6A—N7	−174.51 (9)	N5—C4A—C14A—C1	176.66 (9)
C15—N6—C6A—N7	3.32 (13)	C4—C4A—C14A—C1	−1.14 (14)
C5A—N6—C6A—C12A	5.71 (15)	C2—C1—C14A—C14	178.19 (11)
C15—N6—C6A—C12A	−176.46 (9)	C2—C1—C14A—C4A	−0.16 (16)
N6—C6A—N7—C7A	178.97 (9)	C5A—N6—C15—C16	100.99 (10)
C12A—C6A—N7—C7A	−1.25 (15)	C6A—N6—C15—C16	−76.99 (11)
C6A—N7—C7A—C11A	1.42 (15)	N6—C15—C16—C17	−53.22 (11)
C6A—N7—C7A—C8	−177.56 (10)	C15—C16—C17—N18	−68.56 (11)
N7—C7A—C8—C9	178.05 (11)	O20—S19—C22—C27	13.31 (10)
C11A—C7A—C8—C9	−0.96 (17)	O21—S19—C22—C27	143.85 (9)
C7A—C8—C9—C10	−0.04 (19)	N18—S19—C22—C27	−101.35 (9)
C8—C9—C10—C11	1.32 (19)	O20—S19—C22—C23	−168.77 (8)
C9—C10—C11—C11A	−1.55 (18)	O21—S19—C22—C23	−38.23 (10)
N7—C7A—C11A—C11	−178.25 (10)	N18—S19—C22—C23	76.58 (9)
C8—C7A—C11A—C11	0.72 (15)	C27—C22—C23—C24	0.85 (15)
N7—C7A—C11A—C12	0.08 (15)	S19—C22—C23—C24	−177.05 (8)
C8—C7A—C11A—C12	179.05 (10)	C22—C23—C24—C25	−0.71 (16)
C10—C11—C11A—C7A	0.53 (16)	C23—C24—C25—C26	−0.14 (17)
C10—C11—C11A—C12	−177.68 (11)	C23—C24—C25—C28	−179.19 (10)
C7A—C11A—C12—C12A	−1.76 (15)	C24—C25—C26—C27	0.86 (16)
C11—C11A—C12—C12A	176.50 (10)	C28—C25—C26—C27	179.91 (10)
C11A—C12—C12A—C6A	1.94 (15)	C23—C22—C27—C26	−0.16 (16)
C11A—C12—C12A—S13	−178.82 (8)	S19—C22—C27—C26	177.74 (8)
N7—C6A—C12A—C12	−0.41 (15)	C25—C26—C27—C22	−0.72 (16)
N6—C6A—C12A—C12	179.35 (9)	C16—C17—N18—S19	−167.83 (7)
N7—C6A—C12A—S13	−179.61 (8)	O20—S19—N18—C17	−177.97 (7)
N6—C6A—C12A—S13	0.16 (14)	O21—S19—N18—C17	52.66 (8)
C12—C12A—S13—C13A	176.02 (8)	C22—S19—N18—C17	−62.78 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N18—H18···N5	0.876 (14)	2.243 (15)	2.9973 (12)	144.1 (12)
C15—H15A···O20i	0.99	2.33	3.1641 (12)	141
C11—H11···O21ii	0.95	2.55	3.3933 (13)	149
C15—H15B···S13iii	0.99	2.86	3.6912 (11)	142
C17—H17B···O21iv	0.99	2.47	3.3013 (13)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N18—H18⋯N5	0.876 (14)	2.243 (15)	2.9973 (12)	144.1 (12)
C15—H15A⋯O20i	0.99	2.33	3.1641 (12)	141
C11—H11⋯O21ii	0.95	2.55	3.3933 (13)	149
C15—H15B⋯S13iii	0.99	2.86	3.6912 (11)	142
C17—H17B⋯O21iv	0.99	2.47	3.3013 (13)	141

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