Crystal structure of N-[(naphthalen-1-yl)carbamo-thio-yl]cyclo-hexa-necarboxamide.

The title compound, C18H20N2OS, displays whole-mol-ecule disorder over two adjacent sets of sites with an occupancy ratio of 0.630 (11):0.370 (11). In each disorder component, the cyclo-hexyl ring shows a chair conformation with the exocyclic C-C bond in an equatorial orientation. The dihedral angles between the cyclo-hexyl ring (all atoms) and the naphthyl ring system are 36.9 (6) for the major component and 20.7 (12)° for the minor component. Each component features an intra-molecular N-H⋯O hydrogen bond, which closes an S(5) ring. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R (2) 2(8) loops for both components. Aromatic π-π stacking inter-actions [shortest centroid-centroid separation = 3.593 (9) Å] and a C-H⋯π inter-action are also observed.

Related literature

For background to the varied properties of thio­urea derivatives, see: Sun et al. (2006 ▸); Shen et al. (2006 ▸). For related structures, see: Hu et al. (2011 ▸); Gangadharan et al. (2015 ▸).

Experimental

Crystal data

C18H20N2OS

M = 312.42

Triclinic,

a = 7.0464 (5) Å

b = 11.0379 (5) Å

c = 12.4151 (8) Å

α = 110.873 (3)°

β = 100.660 (3)°

γ = 104.022 (3)°

V = 835.24 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.934, T max = 0.952

14064 measured reflections

2945 independent reflections

1930 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.219

S = 1.05

2945 reflections

404 parameters

1056 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.87 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); 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 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011950/hb7448sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011950/hb7448Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015011950/hb7448Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015011950/hb7448fig1.tif

The mol­ecular structure of the major component of the title compound, with displacement ellipsoids drawn at 40% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015011950/hb7448fig2.tif

Stick plot of both major and minor components of the title compound, with the atoms label for non-H atoms.

Click here for additional data file.

b . DOI: 10.1107/S2056989015011950/hb7448fig3.tif

The crystal packing of the title compound, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1408027

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H20N2OS	Z = 2
Mr = 312.42	F(000) = 332
Triclinic, P1	Dx = 1.242 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0464 (5) Å	Cell parameters from 1930 reflections
b = 11.0379 (5) Å	θ = 2.1–25.0°
c = 12.4151 (8) Å	µ = 0.20 mm−1
α = 110.873 (3)°	T = 293 K
β = 100.660 (3)°	Block, white
γ = 104.022 (3)°	0.35 × 0.30 × 0.25 mm
V = 835.24 (9) Å3

Bruker APEXII CCD diffractometer	2945 independent reflections
Radiation source: fine-focus sealed tube	1930 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scan	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.934, Tmax = 0.952	k = −13→13
14064 measured reflections	l = −14→14

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0972P)2 + 1.1049P] where P = (Fo2 + 2Fc2)/3
2945 reflections	(Δ/σ)max = 0.053
404 parameters	Δρmax = 0.87 e Å−3
1056 restraints	Δρmin = −0.25 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	Occ. (<1)
C1	1.4139 (12)	0.4829 (15)	0.6995 (10)	0.072 (3)	0.630 (11)
C2	1.5803 (14)	0.5008 (15)	0.6610 (8)	0.058 (2)	0.630 (11)
H2	1.5690	0.4550	0.5798	0.069*	0.630 (11)
C3	1.7732 (13)	0.5902 (11)	0.7454 (8)	0.064 (2)	0.630 (11)
H3	1.8908	0.6065	0.7214	0.076*	0.630 (11)
C4	1.7793 (14)	0.6525 (12)	0.8658 (8)	0.065 (2)	0.630 (11)
H4	1.9016	0.7111	0.9257	0.078*	0.630 (11)
C5	1.5918 (13)	0.6230 (12)	0.8936 (7)	0.0446 (17)	0.630 (11)
C6	1.5952 (14)	0.6835 (11)	1.0116 (8)	0.062 (2)	0.630 (11)
H6	1.7193	0.7418	1.0700	0.075*	0.630 (11)
C7	1.4217 (16)	0.6606 (16)	1.0460 (8)	0.082 (3)	0.630 (11)
H7	1.4294	0.7032	1.1270	0.099*	0.630 (11)
C8	1.2357 (16)	0.5753 (16)	0.9622 (9)	0.076 (3)	0.630 (11)
H8	1.1199	0.5574	0.9875	0.091*	0.630 (11)
C9	1.2189 (15)	0.5164 (15)	0.8419 (8)	0.062 (2)	0.630 (11)
H9	1.0919	0.4657	0.7838	0.074*	0.630 (11)
C10	1.4035 (19)	0.536 (2)	0.8090 (10)	0.063 (3)	0.630 (11)
C11	1.1480 (17)	0.2490 (13)	0.5594 (10)	0.042 (2)	0.630 (11)
C12	0.839 (2)	0.2236 (13)	0.4017 (11)	0.042 (3)	0.630 (11)
C13	0.643 (2)	0.113 (2)	0.3153 (11)	0.052 (3)	0.630 (11)
H13	0.6743	0.0287	0.2776	0.062*	0.630 (11)
C14	0.4915 (15)	0.0832 (11)	0.3824 (10)	0.067 (2)	0.630 (11)
H14A	0.4669	0.1674	0.4258	0.080*	0.630 (11)
H14B	0.5514	0.0538	0.4413	0.080*	0.630 (11)
C15	0.2882 (18)	−0.0269 (11)	0.2994 (11)	0.084 (3)	0.630 (11)
H15A	0.1929	−0.0367	0.3455	0.101*	0.630 (11)
H15B	0.3083	−0.1146	0.2629	0.101*	0.630 (11)
C16	0.2014 (19)	0.0145 (14)	0.2016 (11)	0.088 (3)	0.630 (11)
H16A	0.0733	−0.0568	0.1475	0.106*	0.630 (11)
H16B	0.1720	0.0986	0.2389	0.106*	0.630 (11)
C17	0.3457 (16)	0.0371 (10)	0.1289 (11)	0.074 (3)	0.630 (11)
H17A	0.2864	0.0664	0.0697	0.088*	0.630 (11)
H17B	0.3691	−0.0479	0.0865	0.088*	0.630 (11)
C18	0.5478 (15)	0.1477 (9)	0.2156 (9)	0.059 (3)	0.630 (11)
H18A	0.6436	0.1599	0.1703	0.071*	0.630 (11)
H18B	0.5240	0.2342	0.2514	0.071*	0.630 (11)
S1	1.2576 (18)	0.1673 (11)	0.6264 (10)	0.0567 (16)	0.630 (11)
N1	0.938 (2)	0.1781 (12)	0.4817 (12)	0.044 (3)	0.630 (11)
N2	1.2224 (9)	0.3819 (7)	0.5845 (5)	0.0416 (16)	0.630 (11)
O1	0.886 (2)	0.3438 (12)	0.4191 (12)	0.055 (3)	0.630 (11)
C1'	1.4044 (16)	0.4630 (19)	0.6642 (11)	0.032 (3)	0.370 (11)
C2'	1.574 (2)	0.480 (3)	0.6233 (13)	0.063 (4)	0.370 (11)
H2'	1.5553	0.4330	0.5412	0.076*	0.370 (11)
C3'	1.7640 (19)	0.5594 (19)	0.6957 (14)	0.060 (4)	0.370 (11)
H3'	1.8726	0.5649	0.6630	0.072*	0.370 (11)
C4'	1.802 (2)	0.635 (2)	0.8205 (14)	0.070 (4)	0.370 (11)
H4'	1.9328	0.6931	0.8711	0.084*	0.370 (11)
C5'	1.632 (3)	0.618 (3)	0.8638 (14)	0.067 (4)	0.370 (11)
C6'	1.656 (3)	0.682 (3)	0.9838 (16)	0.097 (5)	0.370 (11)
H6'	1.7861	0.7371	1.0373	0.117*	0.370 (11)
C7'	1.489 (3)	0.666 (3)	1.0264 (14)	0.077 (5)	0.370 (11)
H7'	1.5100	0.7078	1.1092	0.092*	0.370 (11)
C8'	1.298 (3)	0.593 (3)	0.9538 (14)	0.070 (4)	0.370 (11)
H8'	1.1874	0.5978	0.9844	0.084*	0.370 (11)
C9'	1.261 (3)	0.507 (3)	0.8293 (12)	0.076 (5)	0.370 (11)
H9'	1.1367	0.4381	0.7805	0.091*	0.370 (11)
C10'	1.434 (2)	0.536 (3)	0.7873 (12)	0.037 (3)	0.370 (11)
C11'	1.100 (3)	0.253 (2)	0.5789 (19)	0.049 (4)	0.370 (11)
C12'	0.809 (3)	0.221 (2)	0.424 (2)	0.042 (4)	0.370 (11)
C13'	0.629 (3)	0.110 (4)	0.3220 (19)	0.051 (4)	0.370 (11)
H13'	0.6531	0.0227	0.3069	0.061*	0.370 (11)
C14'	0.444 (3)	0.103 (3)	0.364 (2)	0.096 (5)	0.370 (11)
H14C	0.4248	0.1923	0.3884	0.116*	0.370 (11)
H14D	0.4647	0.0828	0.4344	0.116*	0.370 (11)
C15'	0.256 (4)	−0.005 (3)	0.2673 (18)	0.102 (6)	0.370 (11)
H15C	0.2702	−0.0944	0.2488	0.123*	0.370 (11)
H15D	0.1378	−0.0039	0.2970	0.123*	0.370 (11)
C16'	0.219 (3)	0.017 (2)	0.1542 (17)	0.081 (5)	0.370 (11)
H16C	0.1000	−0.0564	0.0919	0.098*	0.370 (11)
H16D	0.1951	0.1042	0.1694	0.098*	0.370 (11)
C17'	0.408 (3)	0.018 (2)	0.116 (2)	0.090 (6)	0.370 (11)
H17C	0.3886	0.0311	0.0420	0.108*	0.370 (11)
H17D	0.4230	−0.0711	0.0981	0.108*	0.370 (11)
C18'	0.602 (3)	0.126 (2)	0.2064 (17)	0.083 (5)	0.370 (11)
H18C	0.7176	0.1164	0.1762	0.099*	0.370 (11)
H18D	0.5957	0.2172	0.2197	0.099*	0.370 (11)
S1'	1.222 (3)	0.1767 (19)	0.6457 (17)	0.065 (4)	0.370 (11)
N2'	1.1590 (19)	0.3881 (14)	0.6219 (11)	0.083 (4)	0.370 (11)
N1'	0.972 (3)	0.176 (2)	0.461 (2)	0.036 (4)	0.370 (11)
O1'	0.838 (4)	0.341 (2)	0.448 (2)	0.057 (4)	0.370 (11)
H1A	0.918 (6)	0.0899 (17)	0.454 (4)	0.069*
H2A	1.129 (5)	0.415 (4)	0.560 (3)	0.069*

	U11	U22	U33	U12	U13	U23
C1	0.079 (5)	0.052 (5)	0.075 (7)	0.020 (4)	−0.001 (5)	0.030 (6)
C2	0.071 (4)	0.050 (5)	0.046 (5)	0.024 (3)	0.007 (4)	0.017 (4)
C3	0.072 (4)	0.066 (6)	0.051 (6)	0.026 (4)	0.016 (4)	0.021 (5)
C4	0.054 (4)	0.058 (5)	0.075 (5)	0.014 (3)	−0.001 (4)	0.034 (5)
C5	0.052 (4)	0.031 (3)	0.039 (4)	0.011 (3)	−0.008 (3)	0.013 (3)
C6	0.070 (5)	0.057 (4)	0.070 (4)	0.028 (5)	0.022 (4)	0.033 (4)
C7	0.104 (7)	0.077 (5)	0.068 (5)	0.042 (6)	0.022 (5)	0.027 (4)
C8	0.084 (6)	0.081 (6)	0.080 (5)	0.037 (5)	0.036 (4)	0.043 (4)
C9	0.064 (5)	0.056 (4)	0.066 (4)	0.035 (4)	0.004 (3)	0.024 (3)
C10	0.074 (5)	0.051 (4)	0.063 (5)	0.017 (4)	0.005 (4)	0.032 (4)
C11	0.047 (5)	0.037 (3)	0.035 (4)	0.011 (3)	0.006 (3)	0.012 (3)
C12	0.053 (5)	0.037 (3)	0.032 (4)	0.008 (3)	0.007 (3)	0.017 (3)
C13	0.058 (4)	0.036 (4)	0.053 (4)	0.009 (4)	−0.001 (4)	0.022 (3)
C14	0.058 (5)	0.069 (4)	0.070 (5)	0.021 (3)	0.011 (4)	0.031 (3)
C15	0.066 (5)	0.082 (5)	0.099 (6)	0.007 (4)	0.013 (5)	0.049 (4)
C16	0.063 (5)	0.092 (5)	0.089 (7)	0.005 (4)	−0.012 (5)	0.046 (5)
C17	0.072 (6)	0.056 (4)	0.070 (5)	0.018 (4)	−0.013 (5)	0.020 (4)
C18	0.066 (5)	0.050 (4)	0.055 (4)	0.016 (3)	−0.009 (3)	0.031 (3)
S1	0.069 (3)	0.035 (2)	0.054 (3)	0.0193 (14)	−0.0060 (17)	0.017 (2)
N1	0.056 (5)	0.031 (3)	0.036 (5)	0.009 (3)	−0.001 (4)	0.013 (3)
N2	0.047 (3)	0.033 (3)	0.038 (3)	0.013 (2)	0.001 (2)	0.014 (2)
O1	0.060 (6)	0.036 (3)	0.059 (6)	0.002 (3)	−0.004 (3)	0.028 (3)
C1'	0.049 (5)	0.025 (5)	0.015 (4)	0.012 (4)	−0.004 (3)	0.007 (4)
C2'	0.085 (6)	0.051 (7)	0.041 (7)	0.021 (5)	0.001 (5)	0.014 (6)
C3'	0.053 (6)	0.057 (7)	0.063 (8)	0.018 (5)	0.010 (6)	0.020 (7)
C4'	0.080 (7)	0.060 (7)	0.057 (9)	0.026 (6)	0.004 (7)	0.018 (8)
C5'	0.076 (7)	0.051 (5)	0.060 (7)	0.019 (6)	0.001 (6)	0.020 (6)
C6'	0.103 (9)	0.075 (7)	0.090 (8)	0.025 (8)	−0.001 (7)	0.027 (7)
C7'	0.084 (10)	0.075 (7)	0.080 (7)	0.032 (9)	0.027 (7)	0.038 (6)
C8'	0.079 (8)	0.074 (7)	0.063 (6)	0.028 (7)	0.030 (6)	0.030 (5)
C9'	0.058 (7)	0.055 (6)	0.112 (7)	0.018 (7)	0.004 (6)	0.044 (6)
C10'	0.049 (5)	0.022 (4)	0.025 (5)	0.007 (4)	−0.011 (4)	0.006 (5)
C11'	0.056 (7)	0.032 (5)	0.050 (7)	0.023 (5)	−0.002 (6)	0.011 (5)
C12'	0.053 (6)	0.033 (5)	0.040 (7)	0.008 (5)	0.007 (5)	0.022 (5)
C13'	0.053 (6)	0.041 (6)	0.052 (6)	0.010 (6)	−0.003 (6)	0.024 (5)
C14'	0.073 (8)	0.101 (8)	0.084 (7)	0.009 (7)	0.012 (6)	0.024 (7)
C15'	0.079 (8)	0.104 (8)	0.100 (9)	−0.005 (7)	0.013 (7)	0.047 (7)
C16'	0.069 (7)	0.072 (6)	0.082 (9)	0.011 (6)	−0.005 (8)	0.031 (7)
C17'	0.074 (8)	0.082 (8)	0.074 (7)	0.019 (7)	−0.011 (7)	0.008 (6)
C18'	0.064 (8)	0.083 (8)	0.066 (7)	0.014 (6)	−0.001 (6)	0.010 (6)
S1'	0.074 (7)	0.033 (2)	0.060 (6)	0.020 (3)	−0.016 (4)	0.006 (3)
N2'	0.097 (7)	0.040 (5)	0.065 (7)	0.020 (6)	−0.041 (5)	0.006 (5)
N1'	0.045 (6)	0.028 (4)	0.031 (6)	0.011 (4)	0.009 (4)	0.009 (4)
O1'	0.061 (10)	0.041 (5)	0.058 (9)	0.007 (6)	−0.003 (6)	0.025 (5)

C1—C10	1.298 (10)	C1'—C2'	1.378 (11)
C1—C2	1.344 (9)	C1'—C10'	1.396 (12)
C1—N2	1.589 (8)	C1'—N2'	1.616 (10)
C2—C3	1.416 (9)	C2'—C3'	1.341 (13)
C2—H2	0.9300	C2'—H2'	0.9300
C3—C4	1.392 (8)	C3'—C4'	1.408 (11)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C5	1.418 (9)	C4'—C5'	1.399 (14)
C4—H4	0.9300	C4'—H4'	0.9300
C5—C6	1.370 (9)	C5'—C6'	1.359 (14)
C5—C10	1.392 (11)	C5'—C10'	1.399 (15)
C6—C7	1.364 (9)	C6'—C7'	1.378 (12)
C6—H6	0.9300	C6'—H6'	0.9300
C7—C8	1.373 (10)	C7'—C8'	1.336 (14)
C7—H7	0.9300	C7'—H7'	0.9300
C8—C9	1.369 (9)	C8'—C9'	1.432 (13)
C8—H8	0.9300	C8'—H8'	0.9300
C9—C10	1.424 (10)	C9'—C10'	1.422 (14)
C9—H9	0.9300	C9'—H9'	0.9300
C11—N2	1.329 (14)	C11'—N2'	1.31 (2)
C11—N1	1.451 (19)	C11'—N1'	1.40 (3)
C11—S1	1.653 (6)	C11'—S1'	1.652 (8)
C12—O1	1.214 (6)	C12'—O1'	1.214 (8)
C12—N1	1.411 (9)	C12'—N1'	1.413 (11)
C12—C13	1.502 (7)	C12'—C13'	1.500 (9)
C13—C18	1.511 (10)	C13'—C14'	1.490 (14)
C13—C14	1.512 (8)	C13'—C18'	1.491 (13)
C13—H13	0.9800	C13'—H13'	0.9800
C14—C15	1.520 (8)	C14'—C15'	1.502 (13)
C14—H14A	0.9700	C14'—H14C	0.9700
C14—H14B	0.9700	C14'—H14D	0.9700
C15—C16	1.521 (8)	C15'—C16'	1.495 (13)
C15—H15A	0.9700	C15'—H15C	0.9700
C15—H15B	0.9700	C15'—H15D	0.9700
C16—C17	1.512 (9)	C16'—C17'	1.492 (14)
C16—H16A	0.9700	C16'—H16C	0.9700
C16—H16B	0.9700	C16'—H16D	0.9700
C17—C18	1.526 (8)	C17'—C18'	1.498 (13)
C17—H17A	0.9700	C17'—H17C	0.9700
C17—H17B	0.9700	C17'—H17D	0.9700
C18—H18A	0.9700	C18'—H18C	0.9700
C18—H18B	0.9700	C18'—H18D	0.9700
N1—H1A	0.874 (19)	N2'—H2A	0.927 (18)
N2—H2A	0.883 (18)	N1'—H1A	0.906 (19)
C10—C1—C2	128.3 (8)	C2'—C1'—C10'	117.6 (9)
C10—C1—N2	124.4 (8)	C2'—C1'—N2'	143.7 (10)
C2—C1—N2	107.4 (7)	C10'—C1'—N2'	98.7 (8)
C1—C2—C3	119.2 (6)	C3'—C2'—C1'	123.4 (8)
C1—C2—H2	120.4	C3'—C2'—H2'	118.3
C3—C2—H2	120.4	C1'—C2'—H2'	118.3
C4—C3—C2	117.2 (6)	C2'—C3'—C4'	121.2 (8)
C4—C3—H3	121.4	C2'—C3'—H3'	119.4
C2—C3—H3	121.4	C4'—C3'—H3'	119.4
C3—C4—C5	117.5 (6)	C5'—C4'—C3'	116.1 (10)
C3—C4—H4	121.3	C5'—C4'—H4'	122.0
C5—C4—H4	121.3	C3'—C4'—H4'	121.9
C6—C5—C10	117.4 (6)	C6'—C5'—C10'	117.6 (11)
C6—C5—C4	118.2 (6)	C6'—C5'—C4'	120.2 (12)
C10—C5—C4	124.4 (6)	C10'—C5'—C4'	122.3 (10)
C7—C6—C5	121.9 (7)	C5'—C6'—C7'	120.2 (12)
C7—C6—H6	119.0	C5'—C6'—H6'	119.9
C5—C6—H6	119.0	C7'—C6'—H6'	119.9
C6—C7—C8	120.6 (6)	C8'—C7'—C6'	122.9 (9)
C6—C7—H7	119.7	C8'—C7'—H7'	118.6
C8—C7—H7	119.7	C6'—C7'—H7'	118.5
C9—C8—C7	120.7 (6)	C7'—C8'—C9'	120.3 (9)
C9—C8—H8	119.6	C7'—C8'—H8'	119.8
C7—C8—H8	119.6	C9'—C8'—H8'	119.9
C8—C9—C10	117.4 (7)	C10'—C9'—C8'	113.6 (10)
C8—C9—H9	121.3	C10'—C9'—H9'	123.2
C10—C9—H9	121.3	C8'—C9'—H9'	123.2
C1—C10—C5	113.4 (8)	C5'—C10'—C1'	119.3 (10)
C1—C10—C9	124.9 (9)	C5'—C10'—C9'	123.6 (10)
C5—C10—C9	121.6 (7)	C1'—C10'—C9'	116.6 (11)
N2—C11—N1	115.4 (9)	N2'—C11'—N1'	118.4 (15)
N2—C11—S1	125.6 (9)	N2'—C11'—S1'	120.8 (16)
N1—C11—S1	118.1 (10)	N1'—C11'—S1'	118.6 (18)
O1—C12—N1	122.6 (12)	O1'—C12'—N1'	121 (2)
O1—C12—C13	125.0 (14)	O1'—C12'—C13'	121 (2)
N1—C12—C13	110.6 (11)	N1'—C12'—C13'	115 (2)
C12—C13—C18	112.6 (11)	C14'—C13'—C18'	113 (2)
C12—C13—C14	110.4 (10)	C14'—C13'—C12'	108 (2)
C18—C13—C14	110.4 (11)	C18'—C13'—C12'	114 (2)
C12—C13—H13	107.7	C14'—C13'—H13'	107.2
C18—C13—H13	107.8	C18'—C13'—H13'	107.2
C14—C13—H13	107.7	C12'—C13'—H13'	107.2
C13—C14—C15	112.9 (10)	C13'—C14'—C15'	111 (2)
C13—C14—H14A	109.0	C13'—C14'—H14C	109.3
C15—C14—H14A	109.0	C15'—C14'—H14C	109.3
C13—C14—H14B	109.0	C13'—C14'—H14D	109.4
C15—C14—H14B	109.0	C15'—C14'—H14D	109.3
H14A—C14—H14B	107.8	H14C—C14'—H14D	108.0
C14—C15—C16	109.0 (8)	C16'—C15'—C14'	112.4 (17)
C14—C15—H15A	109.9	C16'—C15'—H15C	109.1
C16—C15—H15A	109.9	C14'—C15'—H15C	109.1
C14—C15—H15B	109.9	C16'—C15'—H15D	109.1
C16—C15—H15B	109.9	C14'—C15'—H15D	109.1
H15A—C15—H15B	108.3	H15C—C15'—H15D	107.9
C17—C16—C15	112.9 (11)	C17'—C16'—C15'	106 (2)
C17—C16—H16A	109.0	C17'—C16'—H16C	110.6
C15—C16—H16A	109.0	C15'—C16'—H16C	110.6
C17—C16—H16B	109.0	C17'—C16'—H16D	110.5
C15—C16—H16B	109.0	C15'—C16'—H16D	110.6
H16A—C16—H16B	107.8	H16C—C16'—H16D	108.7
C16—C17—C18	108.3 (9)	C16'—C17'—C18'	115.5 (19)
C16—C17—H17A	110.0	C16'—C17'—H17C	108.4
C18—C17—H17A	110.0	C18'—C17'—H17C	108.4
C16—C17—H17B	110.0	C16'—C17'—H17D	108.4
C18—C17—H17B	110.0	C18'—C17'—H17D	108.4
H17A—C17—H17B	108.4	H17C—C17'—H17D	107.5
C13—C18—C17	112.9 (9)	C13'—C18'—C17'	109 (2)
C13—C18—H18A	109.0	C13'—C18'—H18C	109.9
C17—C18—H18A	109.0	C17'—C18'—H18C	109.9
C13—C18—H18B	109.0	C13'—C18'—H18D	109.9
C17—C18—H18B	109.0	C17'—C18'—H18D	109.9
H18A—C18—H18B	107.8	H18C—C18'—H18D	108.3
C12—N1—C11	124.0 (12)	C11'—N2'—C1'	114.4 (14)
C12—N1—H1A	117 (3)	C11'—N2'—H2A	110 (3)
C11—N1—H1A	107 (3)	C1'—N2'—H2A	96 (3)
C11—N2—C1	120.8 (9)	C11'—N1'—C12'	117 (2)
C11—N2—H2A	113 (3)	C11'—N1'—H1A	106 (3)
C1—N2—H2A	119 (3)	C12'—N1'—H1A	108 (3)
C10—C1—C2—C3	−2 (3)	C10'—C1'—C2'—C3'	1 (4)
N2—C1—C2—C3	178.3 (12)	N2'—C1'—C2'—C3'	179 (3)
C1—C2—C3—C4	1.6 (19)	C1'—C2'—C3'—C4'	−1 (4)
C2—C3—C4—C5	−0.9 (17)	C2'—C3'—C4'—C5'	2 (3)
C3—C4—C5—C6	180.0 (11)	C3'—C4'—C5'—C6'	177 (3)
C3—C4—C5—C10	0 (2)	C3'—C4'—C5'—C10'	−3 (4)
C10—C5—C6—C7	0 (2)	C10'—C5'—C6'—C7'	0 (4)
C4—C5—C6—C7	180.0 (14)	C4'—C5'—C6'—C7'	180 (3)
C5—C6—C7—C8	0 (2)	C5'—C6'—C7'—C8'	−3 (5)
C6—C7—C8—C9	−3 (3)	C6'—C7'—C8'—C9'	11 (5)
C7—C8—C9—C10	6 (3)	C7'—C8'—C9'—C10'	−16 (4)
C2—C1—C10—C5	1 (3)	C6'—C5'—C10'—C1'	−177 (3)
N2—C1—C10—C5	−178.9 (14)	C4'—C5'—C10'—C1'	3 (4)
C2—C1—C10—C9	177.1 (18)	C6'—C5'—C10'—C9'	−5 (4)
N2—C1—C10—C9	−3 (3)	C4'—C5'—C10'—C9'	174 (3)
C6—C5—C10—C1	180.0 (16)	C2'—C1'—C10'—C5'	−2 (4)
C4—C5—C10—C1	0 (3)	N2'—C1'—C10'—C5'	180 (2)
C6—C5—C10—C9	4 (2)	C2'—C1'—C10'—C9'	−174 (3)
C4—C5—C10—C9	−176.5 (16)	N2'—C1'—C10'—C9'	7 (3)
C8—C9—C10—C1	178 (2)	C8'—C9'—C10'—C5'	13 (4)
C8—C9—C10—C5	−7 (3)	C8'—C9'—C10'—C1'	−175 (3)
O1—C12—C13—C18	24 (2)	O1'—C12'—C13'—C14'	−78 (3)
N1—C12—C13—C18	−170.9 (14)	N1'—C12'—C13'—C14'	123 (3)
O1—C12—C13—C14	−100.1 (15)	O1'—C12'—C13'—C18'	48 (4)
N1—C12—C13—C14	65.1 (18)	N1'—C12'—C13'—C18'	−111 (3)
C12—C13—C14—C15	179.2 (11)	C18'—C13'—C14'—C15'	53 (3)
C18—C13—C14—C15	54.0 (16)	C12'—C13'—C14'—C15'	179.9 (19)
C13—C14—C15—C16	−54.8 (15)	C13'—C14'—C15'—C16'	−57 (3)
C14—C15—C16—C17	57.3 (14)	C14'—C15'—C16'—C17'	57 (3)
C15—C16—C17—C18	−57.7 (13)	C15'—C16'—C17'—C18'	−59 (3)
C12—C13—C18—C17	−178.7 (11)	C14'—C13'—C18'—C17'	−51 (3)
C14—C13—C18—C17	−54.8 (16)	C12'—C13'—C18'—C17'	−175 (2)
C16—C17—C18—C13	56.1 (14)	C16'—C17'—C18'—C13'	56 (3)
O1—C12—N1—C11	−27 (2)	N1'—C11'—N2'—C1'	−120 (2)
C13—C12—N1—C11	167.2 (13)	S1'—C11'—N2'—C1'	43 (2)
N2—C11—N1—C12	23 (2)	C2'—C1'—N2'—C11'	66 (4)
S1—C11—N1—C12	−167.5 (12)	C10'—C1'—N2'—C11'	−116.0 (19)
N1—C11—N2—C1	159.0 (11)	N2'—C11'—N1'—C12'	−43 (3)
S1—C11—N2—C1	−9.9 (13)	S1'—C11'—N1'—C12'	153.6 (19)
C10—C1—N2—C11	−80 (2)	O1'—C12'—N1'—C11'	46 (4)
C2—C1—N2—C11	99.7 (12)	C13'—C12'—N1'—C11'	−156 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.88 (4)	1.97 (4)	2.667 (15)	135 (4)
N2′—H2A···O1′	0.93 (4)	2.03 (4)	2.62 (3)	120 (4)
N1—H1A···S1i	0.87 (3)	2.53 (3)	3.370 (19)	161 (4)
N1′—H1A···S1′i	0.90 (4)	2.59 (4)	3.44 (3)	159 (4)
C18—H18B···Cg1ii	0.90	2.66	3.527 (2)	148

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C1C5/C10 ring.

DHA	DH	HA	D A	DHA
N2H2AO1	0.88(4)	1.97(4)	2.667(15)	135(4)
N2H2AO1	0.93(4)	2.03(4)	2.62(3)	120(4)
N1H1AS1i	0.87(3)	2.53(3)	3.370(19)	161(4)
N1H1AS1i	0.90(4)	2.59(4)	3.44(3)	159(4)
C18H18B Cg1ii	0.90	2.66	3.527(2)	148

Symmetry codes: (i) ; (ii) .