2-(Naphthalen-1-yl)-4-(thio-phen-2-yl-methyl-idene)-1,3-oxazol-5(4H)-one.

The asymmetric unit of the title compound, C(18)H(11)NO(2)S, contains two crystallographically independent mol-ecules. In one mol-ecule, the oxazole and thio-phene rings are oriented at dihedral angles of 17.40 (9) and 18.18 (7)° with respect to the naphthalene ring system, while the oxazole and thio-phene rings are oriented to each other at a dihedral angle of 0.86 (9)°. In the other mol-ecule, the corresponding angles are 3.05 (8), 9.62 (6) and 7.02 (8)°, respectively. In each mol-ecule, a weak intra-molecular C-H⋯N hydrogen bond links the oxazole N atom to the naphthalene group. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure. π-π stacking between the oxazole and thio-phene rings, between the thio-phene and naphthalene rings, and between the oxaozole and naphthalene rings, [centroid-centroid distances = 3.811 (2), 3.889 (2), 3.697 (2) and 3.525 (2) Å] may further stabilize the crystal structure.

Related literature

For potential applications of the title compound, such as organic light-emitting diodes (OLEDs), organic thin-film transistors (OTFTs), and organic photovoltaics (OPVs) of various aromatic ring-based conjugated polymers, see: Liu et al. (2007 ▶); Allard et al. (2008 ▶); Woudenbergh et al. (2004 ▶); Zhang et al. (2007 ▶); Güneş et al. (2007 ▶); Soci et al. (2007 ▶). For the roles of thio­phene-based mol­ecules widely used in the syntheses of the charge-transporting mol­ecules used in organic field effect transistors, organic solar cells and organic light emitting diodes, see: Mas-Torrent & Rovira (2008 ▶); Shirota & Kageyama (2007 ▶); Varis et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H11NO2S

M = 305.35

Monoclinic,

a = 11.1509 (3) Å

b = 7.0871 (2) Å

c = 35.2592 (5) Å

β = 97.914 (4)°

V = 2759.91 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 294 K

0.35 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.921, T max = 0.953

25128 measured reflections

6899 independent reflections

3925 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.133

S = 1.01

6899 reflections

405 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016151/xu5202sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016151/xu5202Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016151/xu5202Isup3.cml

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

C18H11NO2S	F(000) = 1264
Mr = 305.35	Dx = 1.470 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3188 reflections
a = 11.1509 (3) Å	θ = 2.3–22.5°
b = 7.0871 (2) Å	µ = 0.24 mm−1
c = 35.2592 (5) Å	T = 294 K
β = 97.914 (4)°	Block, orange
V = 2759.91 (12) Å3	0.35 × 0.22 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD area-detector diffractometer	6899 independent reflections
Radiation source: fine-focus sealed tube	3925 reflections with I > 2σ(I)
graphite	Rint = 0.061
φ and ω scans	θmax = 28.4°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→12
Tmin = 0.921, Tmax = 0.953	k = −9→9
25128 measured reflections	l = −46→46

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.9624P] where P = (Fo2 + 2Fc2)/3
6899 reflections	(Δ/σ)max = 0.001
405 parameters	Δρmax = 0.44 e Å−3
2 restraints	Δρmin = −0.44 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.99971 (6)	0.92533 (10)	0.81233 (2)	0.02622 (19)
O1	0.95294 (14)	0.9314 (3)	0.66466 (5)	0.0240 (4)
O2	1.15707 (16)	0.9326 (3)	0.66746 (5)	0.0376 (5)
N1	0.93214 (17)	0.9251 (3)	0.72760 (6)	0.0190 (5)
C1	0.7483 (2)	0.9271 (3)	0.67941 (7)	0.0196 (6)
C2	0.6604 (2)	0.8757 (3)	0.70390 (7)	0.0189 (6)
C3	0.6894 (2)	0.8215 (3)	0.74272 (7)	0.0203 (6)
H3	0.7697	0.8241	0.7541	0.024*
C4	0.6018 (2)	0.7657 (4)	0.76358 (8)	0.0238 (6)
H4	0.6232	0.7300	0.7890	0.029*
C5	0.4792 (2)	0.7611 (4)	0.74733 (8)	0.0250 (6)
H5	0.4203	0.7209	0.7618	0.030*
C6	0.4478 (2)	0.8160 (4)	0.71037 (8)	0.0252 (6)
H6	0.3666	0.8148	0.6998	0.030*
C7	0.5358 (2)	0.8747 (4)	0.68781 (8)	0.0222 (6)
C8	0.5026 (2)	0.9324 (4)	0.64940 (8)	0.0259 (6)
H8	0.4211	0.9341	0.6391	0.031*
C9	0.5870 (2)	0.9852 (4)	0.62716 (8)	0.0260 (7)
H9	0.5632	1.0256	0.6022	0.031*
C10	0.7102 (2)	0.9788 (4)	0.64199 (8)	0.0234 (6)
H10	0.7675	1.0102	0.6262	0.028*
C11	0.8774 (2)	0.9272 (3)	0.69294 (7)	0.0200 (6)
C12	1.0706 (2)	0.9308 (4)	0.68424 (8)	0.0255 (6)
C13	1.0557 (2)	0.9265 (4)	0.72456 (7)	0.0205 (6)
C14	1.1464 (2)	0.9264 (4)	0.75406 (8)	0.0217 (6)
H14	1.2267 (16)	0.931 (4)	0.7486 (7)	0.031 (8)*
C15	1.1363 (2)	0.9271 (4)	0.79395 (7)	0.0202 (6)
C16	1.2332 (2)	0.9287 (4)	0.82323 (7)	0.0249 (6)
H16	1.3139	0.9308	0.8193	0.030*
C17	1.1949 (2)	0.9268 (4)	0.85972 (8)	0.0285 (7)
H17	1.2478	0.9270	0.8825	0.034*
C18	1.0734 (2)	0.9248 (4)	0.85800 (8)	0.0272 (7)
H18	1.0337	0.9233	0.8796	0.033*
S1'	0.77988 (6)	0.09732 (10)	0.902561 (19)	0.02376 (18)
O1'	0.83801 (14)	0.2656 (2)	1.04723 (5)	0.0204 (4)
O2'	0.63925 (15)	0.2045 (3)	1.04855 (5)	0.0264 (5)
N1'	0.85670 (17)	0.2013 (3)	0.98541 (6)	0.0169 (5)
C1'	1.0382 (2)	0.3041 (3)	1.02992 (7)	0.0175 (6)
C2'	1.1273 (2)	0.2914 (3)	1.00435 (7)	0.0155 (5)
C3'	1.1032 (2)	0.2400 (4)	0.96522 (7)	0.0195 (6)
H3'	1.0246	0.2082	0.9547	0.023*
C4'	1.1931 (2)	0.2364 (4)	0.94265 (8)	0.0220 (6)
H4'	1.1744	0.2048	0.9169	0.026*
C5'	1.3133 (2)	0.2796 (4)	0.95750 (8)	0.0224 (6)
H5'	1.3739	0.2740	0.9419	0.027*
C6'	1.3403 (2)	0.3296 (4)	0.99488 (8)	0.0226 (6)
H6'	1.4200	0.3575	1.0047	0.027*
C7'	1.2499 (2)	0.3402 (3)	1.01921 (7)	0.0175 (6)
C8'	1.2781 (2)	0.3959 (3)	1.05784 (7)	0.0216 (6)
H8'	1.3580	0.4243	1.0675	0.026*
C9'	1.1912 (2)	0.4091 (3)	1.08129 (7)	0.0218 (6)
H9'	1.2114	0.4485	1.1065	0.026*
C10'	1.0716 (2)	0.3634 (3)	1.06731 (7)	0.0208 (6)
H10'	1.0128	0.3730	1.0835	0.025*
C11'	0.9113 (2)	0.2551 (3)	1.01834 (7)	0.0177 (6)
C12'	0.7230 (2)	0.2106 (3)	1.03059 (7)	0.0197 (6)
C13'	0.7361 (2)	0.1687 (3)	0.99081 (7)	0.0175 (6)
C14'	0.6466 (2)	0.1050 (3)	0.96414 (8)	0.0182 (6)
H14'	0.5738 (16)	0.084 (3)	0.9725 (6)	0.019 (7)*
C15'	0.6534 (2)	0.0608 (3)	0.92518 (7)	0.0181 (6)
C16'	0.5598 (2)	−0.0199 (4)	0.89970 (7)	0.0200 (6)
H16'	0.4840	−0.0495	0.9062	0.024*
C17'	0.5937 (2)	−0.0509 (4)	0.86334 (8)	0.0256 (6)
H17'	0.5430	−0.1050	0.8431	0.031*
C18'	0.7089 (2)	0.0068 (4)	0.86086 (8)	0.0256 (6)
H18'	0.7448	−0.0024	0.8386	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.0254 (4)	0.0327 (4)	0.0211 (4)	−0.0023 (3)	0.0051 (3)	−0.0003 (3)
O1	0.0216 (9)	0.0343 (11)	0.0166 (10)	0.0025 (8)	0.0043 (8)	0.0011 (9)
O2	0.0263 (10)	0.0643 (15)	0.0240 (12)	0.0058 (10)	0.0098 (9)	0.0037 (11)
N1	0.0182 (11)	0.0220 (12)	0.0169 (12)	0.0003 (10)	0.0023 (9)	0.0003 (10)
C1	0.0244 (13)	0.0154 (13)	0.0189 (14)	0.0006 (11)	0.0026 (11)	−0.0023 (12)
C2	0.0212 (13)	0.0147 (13)	0.0200 (15)	0.0007 (11)	−0.0003 (11)	−0.0037 (11)
C3	0.0203 (13)	0.0204 (14)	0.0201 (15)	0.0013 (12)	0.0020 (11)	−0.0012 (12)
C4	0.0264 (15)	0.0210 (15)	0.0239 (16)	0.0002 (12)	0.0028 (12)	0.0013 (12)
C5	0.0236 (14)	0.0215 (15)	0.0312 (18)	0.0002 (12)	0.0083 (12)	−0.0008 (13)
C6	0.0188 (13)	0.0233 (15)	0.0329 (17)	−0.0008 (12)	0.0013 (12)	−0.0044 (13)
C7	0.0253 (14)	0.0173 (14)	0.0228 (15)	0.0019 (12)	−0.0018 (12)	−0.0036 (12)
C8	0.0221 (14)	0.0262 (16)	0.0270 (16)	0.0045 (12)	−0.0050 (12)	−0.0037 (13)
C9	0.0318 (16)	0.0273 (16)	0.0166 (15)	0.0045 (13)	−0.0046 (12)	0.0015 (12)
C10	0.0273 (15)	0.0232 (15)	0.0198 (15)	0.0016 (12)	0.0034 (12)	−0.0027 (12)
C11	0.0232 (13)	0.0160 (14)	0.0214 (15)	0.0019 (12)	0.0056 (11)	0.0013 (12)
C12	0.0232 (14)	0.0280 (16)	0.0251 (16)	0.0020 (13)	0.0026 (12)	0.0011 (13)
C13	0.0199 (13)	0.0211 (14)	0.0213 (15)	0.0011 (12)	0.0053 (11)	0.0016 (12)
C14	0.0203 (14)	0.0205 (15)	0.0249 (16)	−0.0007 (12)	0.0051 (12)	0.0010 (12)
C15	0.0200 (13)	0.0196 (14)	0.0215 (15)	−0.0013 (12)	0.0044 (11)	0.0009 (12)
C16	0.0332 (15)	0.0194 (14)	0.0216 (16)	0.0021 (13)	0.0019 (12)	−0.0039 (13)
C17	0.0339 (16)	0.0276 (16)	0.0214 (16)	0.0029 (13)	−0.0055 (12)	−0.0013 (13)
C18	0.0335 (16)	0.0315 (17)	0.0169 (15)	−0.0015 (14)	0.0044 (12)	0.0012 (13)
S1'	0.0223 (3)	0.0278 (4)	0.0218 (4)	−0.0035 (3)	0.0053 (3)	−0.0007 (3)
O1'	0.0207 (9)	0.0254 (10)	0.0156 (10)	−0.0007 (8)	0.0042 (7)	−0.0004 (8)
O2'	0.0241 (10)	0.0336 (12)	0.0228 (11)	0.0001 (9)	0.0085 (8)	0.0013 (9)
N1'	0.0168 (10)	0.0155 (11)	0.0184 (12)	0.0010 (9)	0.0028 (9)	0.0007 (9)
C1'	0.0202 (13)	0.0121 (13)	0.0204 (14)	0.0011 (11)	0.0035 (11)	0.0004 (11)
C2'	0.0180 (12)	0.0099 (12)	0.0185 (14)	0.0037 (10)	0.0022 (10)	0.0016 (11)
C3'	0.0206 (13)	0.0193 (14)	0.0184 (15)	−0.0004 (11)	0.0018 (11)	−0.0013 (11)
C4'	0.0275 (15)	0.0215 (15)	0.0173 (14)	0.0012 (12)	0.0039 (11)	−0.0008 (12)
C5'	0.0213 (14)	0.0225 (15)	0.0254 (16)	0.0013 (12)	0.0101 (12)	0.0023 (12)
C6'	0.0193 (13)	0.0189 (14)	0.0300 (17)	0.0012 (12)	0.0052 (12)	0.0029 (13)
C7'	0.0189 (13)	0.0108 (13)	0.0221 (15)	0.0009 (11)	0.0005 (11)	0.0037 (11)
C8'	0.0220 (13)	0.0180 (14)	0.0231 (15)	−0.0022 (11)	−0.0031 (11)	0.0021 (12)
C9'	0.0288 (14)	0.0189 (14)	0.0162 (14)	0.0007 (12)	−0.0018 (11)	−0.0020 (12)
C10'	0.0255 (14)	0.0177 (14)	0.0201 (15)	0.0011 (12)	0.0066 (11)	0.0010 (12)
C11'	0.0249 (14)	0.0144 (13)	0.0149 (14)	0.0036 (11)	0.0069 (11)	0.0017 (11)
C12'	0.0186 (13)	0.0172 (14)	0.0232 (15)	0.0024 (12)	0.0030 (11)	0.0037 (12)
C13'	0.0183 (13)	0.0166 (13)	0.0181 (14)	0.0048 (11)	0.0040 (10)	0.0023 (11)
C14'	0.0133 (12)	0.0191 (14)	0.0231 (15)	0.0015 (11)	0.0054 (11)	0.0034 (12)
C15'	0.0174 (12)	0.0173 (13)	0.0200 (15)	0.0018 (11)	0.0036 (11)	0.0053 (12)
C16'	0.0192 (13)	0.0203 (14)	0.0207 (15)	0.0021 (11)	0.0040 (11)	0.0021 (12)
C17'	0.0204 (14)	0.0294 (16)	0.0251 (16)	−0.0003 (12)	−0.0038 (11)	−0.0015 (13)
C18'	0.0292 (15)	0.0331 (16)	0.0149 (15)	0.0064 (13)	0.0048 (12)	0.0021 (12)

S1—C15	1.735 (3)	S1'—C15'	1.732 (2)
S1—C18	1.704 (3)	S1'—C18'	1.697 (3)
O1—C11	1.391 (3)	O1'—C11'	1.393 (3)
O1—C12	1.396 (3)	O1'—C12'	1.391 (3)
O2—C12	1.199 (3)	O2'—C12'	1.199 (3)
N1—C11	1.289 (3)	N1'—C11'	1.292 (3)
N1—C13	1.397 (3)	N1'—C13'	1.403 (3)
C1—C10	1.379 (3)	C1'—C10'	1.385 (3)
C1—C11	1.453 (3)	C2'—C1'	1.434 (3)
C2—C1	1.440 (3)	C3'—C2'	1.417 (3)
C2—C3	1.415 (3)	C3'—C4'	1.363 (3)
C2—C7	1.427 (3)	C3'—H3'	0.9300
C3—H3	0.9300	C4'—H4'	0.9300
C4—C3	1.361 (3)	C5'—C4'	1.404 (3)
C4—H4	0.9300	C5'—C6'	1.358 (3)
C5—C4	1.407 (3)	C5'—H5'	0.9300
C5—C6	1.359 (4)	C6'—H6'	0.9300
C5—H5	0.9300	C7'—C2'	1.437 (3)
C6—C7	1.408 (4)	C7'—C6'	1.412 (3)
C6—H6	0.9300	C8'—C7'	1.412 (3)
C8—C7	1.414 (4)	C8'—C9'	1.361 (3)
C8—C9	1.358 (4)	C8'—H8'	0.9300
C8—H8	0.9300	C9'—C10'	1.394 (3)
C9—C10	1.401 (3)	C9'—H9'	0.9300
C9—H9	0.9300	C10'—H10'	0.9300
C10—H10	0.9300	C11'—C1'	1.459 (3)
C13—C12	1.454 (4)	C13'—C14'	1.351 (3)
C14—C13	1.347 (3)	C13'—C12'	1.460 (3)
C14—H14	0.942 (16)	C14'—H14'	0.913 (16)
C15—C14	1.426 (4)	C15'—C14'	1.421 (3)
C15—C16	1.388 (3)	C15'—C16'	1.402 (3)
C16—H16	0.9300	C16'—C17'	1.403 (4)
C17—C16	1.410 (4)	C16'—H16'	0.9300
C17—H17	0.9300	C17'—H17'	0.9300
C18—C17	1.348 (3)	C18'—C17'	1.362 (3)
C18—H18	0.9300	C18'—H18'	0.9300
C18—S1—C15	91.12 (13)	C18'—S1'—C15'	91.74 (13)
C11—O1—C12	105.42 (19)	C12'—O1'—C11'	106.03 (19)
C11—N1—C13	105.7 (2)	C11'—N1'—C13'	105.6 (2)
C2—C1—C11	122.0 (2)	C2'—C1'—C11'	122.6 (2)
C10—C1—C2	119.7 (2)	C10'—C1'—C2'	119.9 (2)
C10—C1—C11	118.4 (2)	C10'—C1'—C11'	117.5 (2)
C3—C2—C1	124.4 (2)	C1'—C2'—C7'	117.6 (2)
C3—C2—C7	117.6 (2)	C3'—C2'—C1'	125.0 (2)
C7—C2—C1	118.0 (2)	C3'—C2'—C7'	117.4 (2)
C2—C3—H3	119.5	C2'—C3'—H3'	119.4
C4—C3—C2	121.1 (2)	C4'—C3'—C2'	121.1 (2)
C4—C3—H3	119.5	C4'—C3'—H3'	119.4
C3—C4—C5	121.1 (3)	C3'—C4'—C5'	121.3 (2)
C3—C4—H4	119.5	C3'—C4'—H4'	119.4
C5—C4—H4	119.5	C5'—C4'—H4'	119.4
C4—C5—H5	120.3	C4'—C5'—H5'	120.3
C6—C5—C4	119.5 (3)	C6'—C5'—C4'	119.4 (2)
C6—C5—H5	120.3	C6'—C5'—H5'	120.3
C5—C6—C7	121.2 (2)	C5'—C6'—C7'	121.5 (2)
C5—C6—H6	119.4	C5'—C6'—H6'	119.3
C7—C6—H6	119.4	C7'—C6'—H6'	119.3
C6—C7—C2	119.5 (2)	C6'—C7'—C2'	119.2 (2)
C6—C7—C8	121.0 (2)	C8'—C7'—C2'	119.6 (2)
C8—C7—C2	119.4 (2)	C8'—C7'—C6'	121.2 (2)
C7—C8—H8	119.3	C7'—C8'—H8'	119.3
C9—C8—C7	121.5 (2)	C9'—C8'—C7'	121.5 (2)
C9—C8—H8	119.3	C9'—C8'—H8'	119.3
C8—C9—C10	119.8 (3)	C8'—C9'—C10'	119.7 (2)
C8—C9—H9	120.1	C8'—C9'—H9'	120.1
C10—C9—H9	120.1	C10'—C9'—H9'	120.1
C1—C10—C9	121.5 (3)	C1'—C10'—C9'	121.7 (2)
C1—C10—H10	119.2	C1'—C10'—H10'	119.1
C9—C10—H10	119.2	C9'—C10'—H10'	119.1
O1—C11—C1	115.8 (2)	O1'—C11'—C1'	115.2 (2)
N1—C11—O1	115.2 (2)	N1'—C11'—O1'	114.9 (2)
N1—C11—C1	129.0 (2)	N1'—C11'—C1'	129.8 (2)
O1—C12—C13	104.9 (2)	O1'—C12'—C13'	104.7 (2)
O2—C12—O1	121.4 (2)	O2'—C12'—O1'	121.8 (2)
O2—C12—C13	133.7 (2)	O2'—C12'—C13'	133.5 (2)
N1—C13—C12	108.8 (2)	N1'—C13'—C12'	108.8 (2)
C14—C13—N1	125.8 (2)	C14'—C13'—N1'	126.2 (2)
C14—C13—C12	125.5 (2)	C14'—C13'—C12'	125.0 (2)
C13—C14—C15	127.5 (2)	C13'—C14'—C15'	127.8 (2)
C13—C14—H14	118.3 (16)	C13'—C14'—H14'	115.7 (15)
C15—C14—H14	114.2 (16)	C15'—C14'—H14'	116.5 (15)
C14—C15—S1	124.13 (19)	C14'—C15'—S1'	124.58 (19)
C16—C15—S1	110.8 (2)	C16'—C15'—S1'	110.32 (19)
C16—C15—C14	125.0 (2)	C16'—C15'—C14'	125.1 (2)
C15—C16—C17	112.1 (2)	C15'—C16'—C17'	112.3 (2)
C15—C16—H16	124.0	C15'—C16'—H16'	123.9
C17—C16—H16	124.0	C17'—C16'—H16'	123.9
C16—C17—H17	123.6	C16'—C17'—H17'	123.6
C18—C17—C16	112.8 (2)	C18'—C17'—C16'	112.8 (2)
C18—C17—H17	123.6	C18'—C17'—H17'	123.6
S1—C18—H18	123.4	S1'—C18'—H18'	123.5
C17—C18—S1	113.1 (2)	C17'—C18'—S1'	112.9 (2)
C17—C18—H18	123.4	C17'—C18'—H18'	123.5
C15—S1—C18—C17	0.3 (2)	C18'—S1'—C15'—C14'	179.3 (2)
C18—S1—C15—C14	179.3 (2)	C18'—S1'—C15'—C16'	−0.2 (2)
C18—S1—C15—C16	−0.5 (2)	C15'—S1'—C18'—C17'	−0.3 (2)
C12—O1—C11—N1	0.3 (3)	C12'—O1'—C11'—N1'	0.4 (3)
C12—O1—C11—C1	180.0 (2)	C12'—O1'—C11'—C1'	−178.9 (2)
C11—O1—C12—O2	179.5 (3)	C11'—O1'—C12'—O2'	179.7 (2)
C11—O1—C12—C13	−0.1 (3)	C11'—O1'—C12'—C13'	0.0 (2)
C13—N1—C11—O1	−0.4 (3)	C13'—N1'—C11'—O1'	−0.6 (3)
C13—N1—C11—C1	−180.0 (2)	C13'—N1'—C11'—C1'	178.5 (2)
C11—N1—C13—C12	0.3 (3)	C11'—N1'—C13'—C12'	0.6 (3)
C11—N1—C13—C14	179.5 (3)	C11'—N1'—C13'—C14'	−178.0 (2)
C2—C1—C10—C9	0.8 (4)	C2'—C1'—C10'—C9'	−1.0 (4)
C11—C1—C10—C9	−178.8 (2)	C11'—C1'—C10'—C9'	178.5 (2)
C2—C1—C11—O1	164.0 (2)	C3'—C2'—C1'—C10'	−177.3 (2)
C2—C1—C11—N1	−16.4 (4)	C3'—C2'—C1'—C11'	3.2 (4)
C10—C1—C11—O1	−16.3 (3)	C7'—C2'—C1'—C10'	0.6 (3)
C10—C1—C11—N1	163.3 (3)	C7'—C2'—C1'—C11'	−178.9 (2)
C3—C2—C1—C10	−179.6 (2)	C4'—C3'—C2'—C1'	178.2 (2)
C3—C2—C1—C11	0.1 (4)	C4'—C3'—C2'—C7'	0.2 (4)
C7—C2—C1—C10	2.0 (4)	C2'—C3'—C4'—C5'	1.4 (4)
C7—C2—C1—C11	−178.3 (2)	C6'—C5'—C4'—C3'	−1.3 (4)
C1—C2—C3—C4	−176.7 (2)	C4'—C5'—C6'—C7'	−0.3 (4)
C7—C2—C3—C4	1.7 (4)	C6'—C7'—C2'—C1'	−179.9 (2)
C1—C2—C7—C6	176.8 (2)	C6'—C7'—C2'—C3'	−1.8 (3)
C1—C2—C7—C8	−3.1 (4)	C8'—C7'—C2'—C1'	0.6 (3)
C3—C2—C7—C6	−1.7 (4)	C8'—C7'—C2'—C3'	178.8 (2)
C3—C2—C7—C8	178.4 (2)	C2'—C7'—C6'—C5'	1.9 (4)
C5—C4—C3—C2	−0.4 (4)	C8'—C7'—C6'—C5'	−178.7 (2)
C6—C5—C4—C3	−1.0 (4)	C9'—C8'—C7'—C2'	−1.6 (4)
C4—C5—C6—C7	1.0 (4)	C9'—C8'—C7'—C6'	179.0 (2)
C5—C6—C7—C2	0.3 (4)	C7'—C8'—C9'—C10'	1.2 (4)
C5—C6—C7—C8	−179.8 (3)	C8'—C9'—C10'—C1'	0.1 (4)
C9—C8—C7—C2	1.4 (4)	O1'—C11'—C1'—C2'	176.7 (2)
C9—C8—C7—C6	−178.5 (3)	O1'—C11'—C1'—C10'	−2.8 (3)
C7—C8—C9—C10	1.5 (4)	N1'—C11'—C1'—C2'	−2.4 (4)
C8—C9—C10—C1	−2.7 (4)	N1'—C11'—C1'—C10'	178.0 (2)
N1—C13—C12—O1	−0.1 (3)	N1'—C13'—C12'—O1'	−0.4 (3)
N1—C13—C12—O2	−179.6 (3)	N1'—C13'—C12'—O2'	180.0 (3)
C14—C13—C12—O1	−179.3 (3)	C14'—C13'—C12'—O1'	178.3 (2)
C14—C13—C12—O2	1.1 (5)	C14'—C13'—C12'—O2'	−1.4 (5)
C15—C14—C13—N1	−0.9 (5)	N1'—C13'—C14'—C15'	−1.2 (4)
C15—C14—C13—C12	178.3 (3)	C12'—C13'—C14'—C15'	−179.7 (2)
S1—C15—C14—C13	0.9 (4)	S1'—C15'—C14'—C13'	−5.1 (4)
C16—C15—C14—C13	−179.4 (3)	C16'—C15'—C14'—C13'	174.3 (3)
S1—C15—C16—C17	0.5 (3)	S1'—C15'—C16'—C17'	0.7 (3)
C14—C15—C16—C17	−179.3 (3)	C14'—C15'—C16'—C17'	−178.8 (2)
C18—C17—C16—C15	−0.3 (3)	C15'—C16'—C17'—C18'	−0.9 (3)
S1—C18—C17—C16	−0.1 (3)	S1'—C18'—C17'—C16'	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1	0.93	2.27	2.924 (3)	127
C3'—H3'···N1'	0.93	2.29	2.946 (3)	127
C6—H6···O2i	0.93	2.59	3.483 (3)	160
C9'—H9'···O2ii	0.93	2.46	3.310 (3)	152
C16'—H16'···O2'iii	0.93	2.50	3.329 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1	0.93	2.27	2.924 (3)	127
C3′—H3′⋯N1′	0.93	2.29	2.946 (3)	127
C6—H6⋯O2i	0.93	2.59	3.483 (3)	160
C9′—H9′⋯O2ii	0.93	2.46	3.310 (3)	152
C16′—H16′⋯O2′iii	0.93	2.50	3.329 (3)	149

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