(2E)-1-(2,4-Dimethyl-quinolin-3-yl)-3-(thio-phen-2-yl)prop-2-en-1-one.

Two independent but virtually identical mol-ecules comprise the asymmetric unit in the title compound, C(18)H(15)NOS. With reference to the quinolin-3-yl group, the 3-(thio-phen-2-yl)prop-2-en-1-one residue is almost perpendicular, with all but the carbonyl O atom lying to one side of the plane. This conformation is reflected by the C-C-C-C torsion angles of -102.2 (3) and 81.1 (3)° in the two independent mol-ecules. The dihedral angle formed between the 13 non-H atoms directly associated with the quinolin-3-yl group and the thio-phen-2-yl ring is 87.70 (11)° [83.85 (10)° for the second independent mol-ecule]. The presence of C-H⋯O, C-H⋯N and π-π inter-actions [centroid-centroid distance = 3.5590 (12) Å] lead to supra-molecular chains along the c-axis direction. These are connected along the a-axis direction by C-H⋯π inter-actions. The resultant supra-molecular layers stack along the b axis.

Related literature

For background details and biological applications of quinolines, see: Kalluraya & Sreenivasa (1998 ▶); Xiang et al. (2006 ▶). For the biological activity of chalcones, see: Dimmock et al. (1999 ▶); Siddiqui et al. (2008 ▶).

Experimental

Crystal data

C18H15NOS

M = 293.37

Monoclinic,

a = 10.4935 (4) Å

b = 23.8464 (8) Å

c = 11.5464 (4) Å

β = 93.756 (3)°

V = 2883.07 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.947, T max = 0.967

14916 measured reflections

6427 independent reflections

4075 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.160

S = 1.03

6427 reflections

409 parameters

182 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.46 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and Qmol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031485/hg5075sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031485/hg5075Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031485/hg5075Isup3.cml

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

C18H15NOS	F(000) = 1232
Mr = 293.37	Dx = 1.352 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4109 reflections
a = 10.4935 (4) Å	θ = 2.5–29.2°
b = 23.8464 (8) Å	µ = 0.22 mm−1
c = 11.5464 (4) Å	T = 100 K
β = 93.756 (3)°	Block, colourless
V = 2883.07 (18) Å3	0.25 × 0.20 × 0.15 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	6427 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4075 reflections with I > 2σ(I)
Mirror	Rint = 0.040
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −30→22
Tmin = 0.947, Tmax = 0.967	l = −14→11
14916 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.299P] where P = (Fo2 + 2Fc2)/3
6427 reflections	(Δ/σ)max < 0.001
409 parameters	Δρmax = 0.56 e Å−3
182 restraints	Δρmin = −0.46 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
S1	0.30670 (9)	0.05958 (3)	0.34043 (8)	0.0224 (3)	0.765 (2)
S2	1.08225 (8)	0.05541 (3)	0.60970 (7)	0.0228 (3)	0.814 (2)
S1'	0.2891 (5)	0.10382 (16)	0.1135 (4)	0.0224 (3)	0.235 (2)
S2'	1.1144 (6)	0.10712 (19)	0.8273 (5)	0.0228 (3)	0.186 (2)
O1	0.83016 (16)	0.07720 (7)	0.36269 (14)	0.0240 (4)
O2	0.56274 (16)	0.07794 (7)	0.59472 (14)	0.0259 (4)
N1	0.87096 (18)	0.13639 (8)	0.00826 (16)	0.0182 (4)
N2	0.52776 (18)	0.14083 (8)	0.94581 (16)	0.0181 (4)
C1	0.1610 (3)	0.06381 (10)	0.2659 (3)	0.0246 (9)	0.765 (2)
H1	0.0835	0.0521	0.2965	0.029*	0.765 (2)
C2	0.1682 (4)	0.08583 (10)	0.1576 (3)	0.0284 (9)	0.765 (2)
H2	0.0971	0.0912	0.1035	0.034*	0.765 (2)
C3	0.2925 (5)	0.09927 (16)	0.1371 (4)	0.0253 (14)	0.765 (2)
H3	0.3144	0.1157	0.0661	0.030*	0.765 (2)
C1'	0.1608 (11)	0.0803 (2)	0.1824 (9)	0.0246 (9)	0.235 (2)
H1'	0.0755	0.0803	0.1492	0.029*	0.235 (2)
C2'	0.1964 (10)	0.0612 (2)	0.2923 (9)	0.0284 (9)	0.235 (2)
H2'	0.1379	0.0468	0.3442	0.034*	0.235 (2)
C3'	0.3256 (10)	0.0652 (2)	0.3189 (7)	0.0253 (14)	0.235 (2)
H3'	0.3678	0.0542	0.3906	0.030*	0.235 (2)
C4	0.3847 (2)	0.08728 (9)	0.22700 (19)	0.0194 (5)
C5	0.5200 (2)	0.09698 (9)	0.22462 (19)	0.0176 (5)
H5	0.5482	0.1144	0.1569	0.021*
C6	0.6106 (2)	0.08403 (10)	0.3082 (2)	0.0202 (5)
H6	0.5863	0.0667	0.3776	0.024*
C7	0.7457 (2)	0.09599 (9)	0.29473 (19)	0.0179 (5)
C8	0.8360 (2)	0.04453 (10)	0.0864 (2)	0.0245 (6)
H8A	0.8668	0.0341	0.0111	0.037*
H8B	0.7505	0.0289	0.0934	0.037*
H8C	0.8944	0.0296	0.1487	0.037*
C9	0.8305 (2)	0.10735 (10)	0.09594 (19)	0.0176 (5)
C10	0.7826 (2)	0.13304 (9)	0.19578 (19)	0.0173 (5)
C11	0.7760 (2)	0.19024 (9)	0.20381 (19)	0.0168 (5)
C12	0.7250 (2)	0.21978 (10)	0.3063 (2)	0.0202 (5)
H12A	0.6995	0.1920	0.3628	0.030*
H12B	0.6507	0.2425	0.2802	0.030*
H12C	0.7915	0.2441	0.3426	0.030*
C13	0.8209 (2)	0.22287 (9)	0.11100 (19)	0.0164 (5)
C14	0.8211 (2)	0.28242 (10)	0.1100 (2)	0.0204 (5)
H14	0.7912	0.3024	0.1740	0.024*
C15	0.8636 (2)	0.31132 (10)	0.0179 (2)	0.0221 (5)
H15	0.8635	0.3512	0.0185	0.027*
C16	0.9074 (2)	0.28255 (10)	−0.0774 (2)	0.0213 (5)
H16	0.9358	0.3030	−0.1415	0.026*
C17	0.9096 (2)	0.22560 (10)	−0.0792 (2)	0.0198 (5)
H17	0.9405	0.2067	−0.1441	0.024*
C18	0.8664 (2)	0.19410 (9)	0.01481 (19)	0.0162 (5)
C19	1.2324 (3)	0.06405 (10)	0.6756 (3)	0.0227 (8)	0.814 (2)
H19	1.3088	0.0523	0.6429	0.027*	0.814 (2)
C20	1.2283 (3)	0.08988 (9)	0.7808 (3)	0.0262 (8)	0.814 (2)
H20	1.3016	0.0983	0.8304	0.031*	0.814 (2)
C21	1.1044 (5)	0.10228 (15)	0.8064 (4)	0.0231 (12)	0.814 (2)
H21	1.0851	0.1205	0.8763	0.028*	0.814 (2)
C19'	1.2382 (12)	0.0828 (3)	0.7536 (10)	0.0227 (8)	0.186 (2)
H19B	1.3253	0.0851	0.7812	0.027*	0.186 (2)
C20'	1.1962 (11)	0.0594 (3)	0.6493 (9)	0.0262 (8)	0.186 (2)
H20B	1.2514	0.0437	0.5959	0.031*	0.186 (2)
C21'	1.0652 (12)	0.0613 (2)	0.6307 (7)	0.0231 (12)	0.186 (2)
H21B	1.0189	0.0473	0.5633	0.028*	0.186 (2)
C22	1.0104 (2)	0.08626 (9)	0.72294 (19)	0.0186 (5)
C23	0.8752 (2)	0.09631 (9)	0.7276 (2)	0.0172 (5)
H23	0.8484	0.1127	0.7970	0.021*
C24	0.7833 (2)	0.08503 (9)	0.6447 (2)	0.0185 (5)
H24	0.8061	0.0684	0.5742	0.022*
C25	0.6489 (2)	0.09748 (9)	0.6595 (2)	0.0184 (5)
C26	0.6714 (2)	0.22170 (10)	0.6441 (2)	0.0211 (5)
H26A	0.6954	0.1934	0.5880	0.032*
H26B	0.7465	0.2441	0.6692	0.032*
H26C	0.6054	0.2463	0.6078	0.032*
C27	0.6204 (2)	0.19306 (10)	0.74765 (19)	0.0173 (5)
C28	0.6142 (2)	0.13577 (9)	0.75760 (19)	0.0160 (5)
C29	0.5674 (2)	0.11100 (10)	0.85886 (19)	0.0176 (5)
C30	0.5630 (2)	0.04845 (9)	0.8706 (2)	0.0239 (6)
H30A	0.5345	0.0386	0.9471	0.036*
H30B	0.6484	0.0329	0.8623	0.036*
H30C	0.5033	0.0329	0.8101	0.036*
C31	0.5763 (2)	0.22622 (9)	0.84016 (19)	0.0161 (5)
C32	0.5758 (2)	0.28574 (10)	0.8390 (2)	0.0201 (5)
H32	0.6059	0.3052	0.7744	0.024*
C33	0.5327 (2)	0.31534 (10)	0.9295 (2)	0.0233 (6)
H33	0.5322	0.3552	0.9271	0.028*
C34	0.4888 (2)	0.28715 (10)	1.0269 (2)	0.0227 (6)
H34	0.4601	0.3081	1.0901	0.027*
C35	0.4877 (2)	0.22986 (10)	1.0305 (2)	0.0203 (5)
H35	0.4573	0.2112	1.0960	0.024*
C36	0.5314 (2)	0.19812 (9)	0.93734 (19)	0.0163 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0241 (5)	0.0243 (5)	0.0195 (5)	−0.0060 (4)	0.0075 (3)	−0.0004 (3)
S2	0.0227 (5)	0.0262 (5)	0.0201 (4)	0.0063 (3)	0.0063 (3)	−0.0009 (3)
S1'	0.0241 (5)	0.0243 (5)	0.0195 (5)	−0.0060 (4)	0.0075 (3)	−0.0004 (3)
S2'	0.0227 (5)	0.0262 (5)	0.0201 (4)	0.0063 (3)	0.0063 (3)	−0.0009 (3)
O1	0.0256 (10)	0.0285 (10)	0.0174 (9)	0.0003 (8)	−0.0019 (8)	0.0032 (7)
O2	0.0213 (9)	0.0341 (10)	0.0220 (9)	−0.0001 (8)	−0.0015 (8)	−0.0057 (8)
N1	0.0164 (10)	0.0207 (10)	0.0176 (10)	−0.0011 (8)	0.0014 (8)	−0.0021 (8)
N2	0.0173 (10)	0.0211 (10)	0.0160 (10)	0.0017 (8)	0.0027 (8)	0.0009 (8)
C1	0.0109 (15)	0.0289 (18)	0.034 (2)	−0.0063 (14)	0.0056 (16)	−0.0078 (16)
C2	0.0205 (18)	0.034 (2)	0.031 (2)	−0.0014 (15)	0.0037 (16)	0.0022 (16)
C3	0.023 (2)	0.035 (2)	0.018 (3)	−0.0026 (16)	−0.0002 (19)	0.0067 (18)
C1'	0.0109 (15)	0.0289 (18)	0.034 (2)	−0.0063 (14)	0.0056 (16)	−0.0078 (16)
C2'	0.0205 (18)	0.034 (2)	0.031 (2)	−0.0014 (15)	0.0037 (16)	0.0022 (16)
C3'	0.023 (2)	0.035 (2)	0.018 (3)	−0.0026 (16)	−0.0002 (19)	0.0067 (18)
C4	0.0207 (13)	0.0170 (12)	0.0211 (13)	−0.0017 (10)	0.0062 (10)	−0.0041 (10)
C5	0.0215 (13)	0.0170 (11)	0.0151 (11)	−0.0038 (10)	0.0071 (10)	−0.0024 (9)
C6	0.0235 (13)	0.0211 (12)	0.0168 (12)	−0.0040 (10)	0.0064 (10)	−0.0020 (10)
C7	0.0234 (13)	0.0170 (12)	0.0136 (11)	−0.0003 (10)	0.0034 (10)	−0.0026 (9)
C8	0.0302 (14)	0.0206 (13)	0.0234 (13)	−0.0020 (11)	0.0065 (11)	−0.0035 (10)
C9	0.0172 (12)	0.0215 (12)	0.0141 (11)	−0.0014 (10)	−0.0005 (10)	−0.0014 (9)
C10	0.0129 (12)	0.0242 (12)	0.0147 (11)	−0.0028 (10)	0.0008 (9)	0.0007 (9)
C11	0.0112 (11)	0.0236 (12)	0.0157 (11)	−0.0009 (10)	0.0003 (9)	−0.0030 (10)
C12	0.0203 (13)	0.0225 (12)	0.0183 (12)	0.0009 (10)	0.0053 (10)	−0.0037 (10)
C13	0.0114 (11)	0.0202 (12)	0.0173 (12)	0.0001 (9)	−0.0009 (9)	−0.0010 (9)
C14	0.0161 (12)	0.0215 (13)	0.0234 (13)	0.0018 (10)	0.0002 (10)	−0.0043 (10)
C15	0.0189 (13)	0.0192 (12)	0.0279 (14)	0.0017 (10)	−0.0009 (11)	0.0047 (10)
C16	0.0169 (13)	0.0269 (13)	0.0202 (13)	−0.0002 (10)	0.0016 (10)	0.0074 (10)
C17	0.0167 (12)	0.0260 (13)	0.0168 (12)	−0.0005 (10)	0.0030 (10)	0.0001 (10)
C18	0.0108 (11)	0.0218 (12)	0.0159 (12)	−0.0025 (10)	−0.0003 (9)	0.0000 (9)
C19	0.0129 (15)	0.0265 (17)	0.0296 (19)	0.0053 (13)	0.0086 (14)	0.0095 (14)
C20	0.0179 (16)	0.0256 (16)	0.035 (2)	0.0010 (13)	−0.0009 (15)	−0.0017 (14)
C21	0.024 (2)	0.0246 (19)	0.020 (2)	0.0005 (14)	−0.0058 (17)	−0.0020 (16)
C19'	0.0129 (15)	0.0265 (17)	0.0296 (19)	0.0053 (13)	0.0086 (14)	0.0095 (14)
C20'	0.0179 (16)	0.0256 (16)	0.035 (2)	0.0010 (13)	−0.0009 (15)	−0.0017 (14)
C21'	0.024 (2)	0.0246 (19)	0.020 (2)	0.0005 (14)	−0.0058 (17)	−0.0020 (16)
C22	0.0215 (13)	0.0156 (11)	0.0192 (12)	0.0012 (10)	0.0052 (10)	0.0023 (9)
C23	0.0202 (13)	0.0155 (11)	0.0164 (12)	−0.0013 (10)	0.0059 (10)	0.0014 (9)
C24	0.0197 (13)	0.0208 (12)	0.0154 (12)	0.0019 (10)	0.0038 (10)	0.0001 (10)
C25	0.0200 (13)	0.0197 (12)	0.0155 (12)	0.0002 (10)	0.0025 (10)	0.0031 (9)
C26	0.0209 (13)	0.0250 (13)	0.0179 (12)	−0.0004 (10)	0.0043 (10)	0.0030 (10)
C27	0.0119 (12)	0.0227 (12)	0.0171 (12)	−0.0015 (10)	−0.0001 (9)	0.0032 (10)
C28	0.0114 (11)	0.0228 (12)	0.0141 (11)	0.0039 (9)	0.0016 (9)	−0.0001 (9)
C29	0.0143 (12)	0.0218 (12)	0.0168 (12)	0.0016 (10)	0.0012 (9)	0.0023 (10)
C30	0.0313 (14)	0.0176 (12)	0.0232 (13)	0.0005 (11)	0.0064 (11)	0.0031 (10)
C31	0.0108 (11)	0.0196 (12)	0.0180 (12)	0.0007 (9)	0.0017 (9)	−0.0009 (9)
C32	0.0178 (13)	0.0209 (12)	0.0216 (13)	−0.0017 (10)	0.0013 (10)	0.0032 (10)
C33	0.0179 (13)	0.0189 (12)	0.0330 (15)	0.0002 (10)	0.0011 (11)	−0.0040 (11)
C34	0.0179 (13)	0.0265 (13)	0.0237 (13)	0.0011 (10)	0.0016 (10)	−0.0090 (11)
C35	0.0167 (12)	0.0250 (13)	0.0195 (13)	0.0024 (10)	0.0027 (10)	−0.0010 (10)
C36	0.0109 (11)	0.0218 (12)	0.0163 (12)	0.0010 (9)	0.0011 (9)	0.0003 (10)

S1—C1	1.708 (3)	C14—H14	0.9500
S1—C4	1.721 (2)	C15—C16	1.399 (3)
S2—C22	1.717 (2)	C15—H15	0.9500
S2—C19	1.717 (3)	C16—C17	1.358 (3)
S1'—C4	1.646 (5)	C16—H16	0.9500
S1'—C1'	1.704 (8)	C17—C18	1.418 (3)
S2'—C22	1.649 (6)	C17—H17	0.9500
S2'—C19'	1.700 (8)	C19—C20	1.365 (4)
O1—C7	1.229 (3)	C19—H19	0.9500
O2—C25	1.227 (3)	C20—C21	1.384 (5)
N1—C9	1.319 (3)	C20—H20	0.9500
N1—C18	1.379 (3)	C21—C22	1.387 (4)
N2—C29	1.320 (3)	C21—H21	0.9500
N2—C36	1.370 (3)	C19'—C20'	1.374 (8)
C1—C2	1.362 (4)	C19'—H19B	0.9500
C1—H1	0.9500	C20'—C21'	1.379 (8)
C2—C3	1.379 (5)	C20'—H20B	0.9500
C2—H2	0.9500	C21'—C22	1.378 (7)
C3—C4	1.401 (5)	C21'—H21B	0.9500
C3—H3	0.9500	C22—C23	1.443 (3)
C1'—C2'	1.377 (8)	C23—C24	1.341 (3)
C1'—H1'	0.9500	C23—H23	0.9500
C2'—C3'	1.373 (8)	C24—C25	1.461 (3)
C2'—H2'	0.9500	C24—H24	0.9500
C3'—C4	1.369 (7)	C25—C28	1.517 (3)
C3'—H3'	0.9500	C26—C27	1.505 (3)
C4—C5	1.440 (3)	C26—H26A	0.9800
C5—C6	1.345 (3)	C26—H26B	0.9800
C5—H5	0.9500	C26—H26C	0.9800
C6—C7	1.465 (3)	C27—C28	1.373 (3)
C6—H6	0.9500	C27—C31	1.430 (3)
C7—C10	1.515 (3)	C28—C29	1.426 (3)
C8—C9	1.503 (3)	C29—C30	1.499 (3)
C8—H8A	0.9800	C30—H30A	0.9800
C8—H8B	0.9800	C30—H30B	0.9800
C8—H8C	0.9800	C30—H30C	0.9800
C9—C10	1.426 (3)	C31—C36	1.414 (3)
C10—C11	1.369 (3)	C31—C32	1.420 (3)
C11—C13	1.429 (3)	C32—C33	1.362 (3)
C11—C12	1.505 (3)	C32—H32	0.9500
C12—H12A	0.9800	C33—C34	1.413 (3)
C12—H12B	0.9800	C33—H33	0.9500
C12—H12C	0.9800	C34—C35	1.367 (3)
C13—C18	1.415 (3)	C34—H34	0.9500
C13—C14	1.420 (3)	C35—C36	1.416 (3)
C14—C15	1.367 (3)	C35—H35	0.9500
C1—S1—C4	92.77 (15)	N1—C18—C13	122.8 (2)
C22—S2—C19	92.72 (14)	N1—C18—C17	118.2 (2)
C4—S1'—C1'	90.5 (5)	C13—C18—C17	119.0 (2)
C22—S2'—C19'	91.3 (5)	C20—C19—S2	111.5 (2)
C9—N1—C18	117.9 (2)	C20—C19—H19	124.2
C29—N2—C36	118.1 (2)	S2—C19—H19	124.2
C2—C1—S1	112.5 (3)	C19—C20—C21	111.8 (3)
C2—C1—H1	123.7	C19—C20—H20	124.1
S1—C1—H1	123.7	C21—C20—H20	124.1
C1—C2—C3	110.9 (3)	C22—C21—C20	115.3 (4)
C1—C2—H2	124.5	C22—C21—H21	122.3
C3—C2—H2	124.5	C20—C21—H21	122.3
C2—C3—C4	116.1 (4)	C20'—C19'—S2'	111.5 (8)
C2—C3—H3	121.9	C20'—C19'—H19B	124.3
C4—C3—H3	121.9	S2'—C19'—H19B	124.3
C2'—C1'—S1'	111.3 (8)	C19'—C20'—C21'	112.5 (7)
C2'—C1'—H1'	124.3	C19'—C20'—H20B	123.8
S1'—C1'—H1'	124.3	C21'—C20'—H20B	123.8
C3'—C2'—C1'	112.8 (7)	C20'—C21'—C22	110.8 (6)
C3'—C2'—H2'	123.6	C20'—C21'—H21B	124.6
C1'—C2'—H2'	123.6	C22—C21'—H21B	124.6
C2'—C3'—C4	110.2 (6)	C21—C22—C21'	110.0 (6)
C2'—C3'—H3'	124.9	C21—C22—C23	125.8 (3)
C4—C3'—H3'	124.9	C21'—C22—C23	124.2 (6)
C3—C4—C3'	109.1 (6)	C21—C22—S2'	3.9 (4)
C3—C4—C5	125.9 (3)	C21'—C22—S2'	113.9 (5)
C3'—C4—C5	125.0 (5)	C23—C22—S2'	121.9 (3)
C3—C4—S1'	6.1 (4)	C21—C22—S2	108.6 (3)
C3'—C4—S1'	115.2 (5)	C21'—C22—S2	1.4 (5)
C5—C4—S1'	119.8 (3)	C23—C22—S2	125.55 (17)
C3—C4—S1	107.6 (3)	S2'—C22—S2	112.5 (3)
C3'—C4—S1	1.5 (5)	C24—C23—C22	127.1 (2)
C5—C4—S1	126.48 (17)	C24—C23—H23	116.5
S1'—C4—S1	113.7 (2)	C22—C23—H23	116.5
C6—C5—C4	126.9 (2)	C23—C24—C25	122.0 (2)
C6—C5—H5	116.6	C23—C24—H24	119.0
C4—C5—H5	116.6	C25—C24—H24	119.0
C5—C6—C7	121.5 (2)	O2—C25—C24	122.0 (2)
C5—C6—H6	119.3	O2—C25—C28	118.7 (2)
C7—C6—H6	119.3	C24—C25—C28	119.36 (19)
O1—C7—C6	121.6 (2)	C27—C26—H26A	109.5
O1—C7—C10	119.0 (2)	C27—C26—H26B	109.5
C6—C7—C10	119.41 (19)	H26A—C26—H26B	109.5
C9—C8—H8A	109.5	C27—C26—H26C	109.5
C9—C8—H8B	109.5	H26A—C26—H26C	109.5
H8A—C8—H8B	109.5	H26B—C26—H26C	109.5
C9—C8—H8C	109.5	C28—C27—C31	117.9 (2)
H8A—C8—H8C	109.5	C28—C27—C26	122.6 (2)
H8B—C8—H8C	109.5	C31—C27—C26	119.4 (2)
N1—C9—C10	122.9 (2)	C27—C28—C29	120.1 (2)
N1—C9—C8	116.8 (2)	C27—C28—C25	121.4 (2)
C10—C9—C8	120.3 (2)	C29—C28—C25	118.4 (2)
C11—C10—C9	120.3 (2)	N2—C29—C28	122.9 (2)
C11—C10—C7	120.9 (2)	N2—C29—C30	117.0 (2)
C9—C10—C7	118.7 (2)	C28—C29—C30	120.1 (2)
C10—C11—C13	118.1 (2)	C29—C30—H30A	109.5
C10—C11—C12	122.8 (2)	C29—C30—H30B	109.5
C13—C11—C12	119.1 (2)	H30A—C30—H30B	109.5
C11—C12—H12A	109.5	C29—C30—H30C	109.5
C11—C12—H12B	109.5	H30A—C30—H30C	109.5
H12A—C12—H12B	109.5	H30B—C30—H30C	109.5
C11—C12—H12C	109.5	C36—C31—C32	118.7 (2)
H12A—C12—H12C	109.5	C36—C31—C27	118.2 (2)
H12B—C12—H12C	109.5	C32—C31—C27	123.2 (2)
C18—C13—C14	118.5 (2)	C33—C32—C31	120.8 (2)
C18—C13—C11	118.0 (2)	C33—C32—H32	119.6
C14—C13—C11	123.5 (2)	C31—C32—H32	119.6
C15—C14—C13	120.7 (2)	C32—C33—C34	120.4 (2)
C15—C14—H14	119.6	C32—C33—H33	119.8
C13—C14—H14	119.6	C34—C33—H33	119.8
C14—C15—C16	120.4 (2)	C35—C34—C33	120.3 (2)
C14—C15—H15	119.8	C35—C34—H34	119.9
C16—C15—H15	119.8	C33—C34—H34	119.9
C17—C16—C15	120.6 (2)	C34—C35—C36	120.5 (2)
C17—C16—H16	119.7	C34—C35—H35	119.8
C15—C16—H16	119.7	C36—C35—H35	119.8
C16—C17—C18	120.8 (2)	N2—C36—C31	122.8 (2)
C16—C17—H17	119.6	N2—C36—C35	117.8 (2)
C18—C17—H17	119.6	C31—C36—C35	119.4 (2)
C4—S1—C1—C2	−0.36 (11)	C22—S2—C19—C20	−0.20 (10)
S1—C1—C2—C3	−0.33 (19)	S2—C19—C20—C21	−0.04 (19)
C1—C2—C3—C4	1.1 (3)	C19—C20—C21—C22	0.3 (3)
C4—S1'—C1'—C2'	1.0 (4)	C22—S2'—C19'—C20'	0.5 (4)
S1'—C1'—C2'—C3'	−0.7 (6)	S2'—C19'—C20'—C21'	−0.2 (6)
C1'—C2'—C3'—C4	−0.2 (6)	C19'—C20'—C21'—C22	−0.3 (6)
C2—C3—C4—C3'	−1.4 (4)	C20—C21—C22—C21'	−0.5 (4)
C2—C3—C4—C5	179.2 (2)	C20—C21—C22—C23	−177.6 (2)
C2—C3—C4—S1	−1.3 (3)	C20—C21—C22—S2	−0.5 (3)
C2'—C3'—C4—C3	0.9 (5)	C20'—C21'—C22—C21	0.4 (5)
C2'—C3'—C4—C5	−179.6 (3)	C20'—C21'—C22—C23	177.6 (3)
C2'—C3'—C4—S1'	1.0 (5)	C20'—C21'—C22—S2'	0.6 (5)
C2'—C3'—C4—S1	−1(8)	C20'—C21'—C22—S2	−1(8)
C1'—S1'—C4—C3	−1(2)	C19'—S2'—C22—C21	2(4)
C1'—S1'—C4—C3'	−1.2 (4)	C19'—S2'—C22—C21'	−0.6 (4)
C1'—S1'—C4—C5	179.4 (2)	C19'—S2'—C22—C23	−177.7 (2)
C1'—S1'—C4—S1	−1.1 (3)	C19'—S2'—C22—S2	−0.6 (3)
C1—S1—C4—C3	0.9 (2)	C19—S2—C22—C21	0.38 (19)
C1—S1—C4—C5	−179.6 (2)	C19—S2—C22—C23	177.5 (2)
C1—S1—C4—S1'	0.96 (18)	C19—S2—C22—S2'	0.55 (19)
C3—C4—C5—C6	−177.5 (3)	C21—C22—C23—C24	174.7 (3)
C3'—C4—C5—C6	3.1 (4)	C21'—C22—C23—C24	−2.0 (4)
S1'—C4—C5—C6	−177.5 (2)	S2'—C22—C23—C24	174.8 (2)
S1—C4—C5—C6	3.1 (4)	S2—C22—C23—C24	−2.0 (3)
C4—C5—C6—C7	179.7 (2)	C22—C23—C24—C25	−179.7 (2)
C5—C6—C7—O1	−169.4 (2)	C23—C24—C25—O2	−165.9 (2)
C5—C6—C7—C10	11.5 (3)	C23—C24—C25—C28	14.3 (3)
C18—N1—C9—C10	0.1 (3)	C31—C27—C28—C29	−1.2 (3)
C18—N1—C9—C8	179.80 (19)	C26—C27—C28—C29	178.7 (2)
N1—C9—C10—C11	0.5 (3)	C31—C27—C28—C25	175.06 (19)
C8—C9—C10—C11	−179.1 (2)	C26—C27—C28—C25	−5.0 (3)
N1—C9—C10—C7	−176.5 (2)	O2—C25—C28—C27	−98.7 (3)
C8—C9—C10—C7	3.9 (3)	C24—C25—C28—C27	81.1 (3)
O1—C7—C10—C11	−98.3 (3)	O2—C25—C28—C29	77.7 (3)
C6—C7—C10—C11	80.8 (3)	C24—C25—C28—C29	−102.5 (3)
O1—C7—C10—C9	78.7 (3)	C36—N2—C29—C28	0.4 (3)
C6—C7—C10—C9	−102.2 (3)	C36—N2—C29—C30	179.72 (19)
C9—C10—C11—C13	−1.4 (3)	C27—C28—C29—N2	0.4 (3)
C7—C10—C11—C13	175.53 (19)	C25—C28—C29—N2	−176.0 (2)
C9—C10—C11—C12	179.3 (2)	C27—C28—C29—C30	−178.8 (2)
C7—C10—C11—C12	−3.8 (3)	C25—C28—C29—C30	4.7 (3)
C10—C11—C13—C18	1.7 (3)	C28—C27—C31—C36	1.2 (3)
C12—C11—C13—C18	−178.99 (19)	C26—C27—C31—C36	−178.75 (19)
C10—C11—C13—C14	−178.9 (2)	C28—C27—C31—C32	−178.9 (2)
C12—C11—C13—C14	0.4 (3)	C26—C27—C31—C32	1.2 (3)
C18—C13—C14—C15	0.3 (3)	C36—C31—C32—C33	−0.1 (3)
C11—C13—C14—C15	−179.1 (2)	C27—C31—C32—C33	180.0 (2)
C13—C14—C15—C16	0.3 (3)	C31—C32—C33—C34	0.6 (3)
C14—C15—C16—C17	−0.8 (3)	C32—C33—C34—C35	−0.9 (3)
C15—C16—C17—C18	0.7 (3)	C33—C34—C35—C36	0.6 (3)
C9—N1—C18—C13	0.2 (3)	C29—N2—C36—C31	−0.4 (3)
C9—N1—C18—C17	−179.94 (19)	C29—N2—C36—C35	179.47 (19)
C14—C13—C18—N1	179.5 (2)	C32—C31—C36—N2	179.7 (2)
C11—C13—C18—N1	−1.1 (3)	C27—C31—C36—N2	−0.4 (3)
C14—C13—C18—C17	−0.4 (3)	C32—C31—C36—C35	−0.2 (3)
C11—C13—C18—C17	179.03 (19)	C27—C31—C36—C35	179.71 (19)
C16—C17—C18—N1	−180.0 (2)	C34—C35—C36—N2	−179.9 (2)
C16—C17—C18—C13	−0.1 (3)	C34—C35—C36—C31	0.0 (3)

Cg1 and Cg2 are the centroids of the C31–C36 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2i	0.95	2.51	3.391 (3)	154
C6—H6···O2	0.95	2.55	3.382 (3)	146
C23—H23···N1ii	0.95	2.50	3.382 (3)	154
C24—H24···O1	0.95	2.48	3.330 (3)	149
C12—H12c···Cg1iii	0.98	2.67	142	3.499 (2)
C26—H26c···Cg2iv	0.98	2.67	143	3.503 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C31–C36 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2i	0.95	2.51	3.391 (3)	154
C6—H6⋯O2	0.95	2.55	3.382 (3)	146
C23—H23⋯N1ii	0.95	2.50	3.382 (3)	154
C24—H24⋯O1	0.95	2.48	3.330 (3)	149
C12—H12c⋯Cg1iii	0.98	2.67	142	4 (1)
C26—H26c⋯Cg2iv	0.98	2.67	143	4 (1)

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