Crystal structure of N-[(naphthalen-1-yl)carbamo­thio­yl]cyclo­hexa­necarboxamide

Vimala, G.; Haribabu, J.; Aishwarya, S.; Karvembu, R.; SubbiahPandi, A.

doi:10.1107/S2056989015011950

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o508-o509

doi:10.1107/S2056989015011950

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Crystal structure of N-[(naphthalen-1-yl)carbamothioyl]cyclohexanecarboxamide

G. Vimala,^a J. Haribabu,^b S. Aishwarya,^b R. Karvembu ^b and A. SubbiahPandi ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Chemistry, National Institute of Technology, Trichy 620 015, India
^*Correspondence e-mail: aspandian59@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 14 June 2015; accepted 22 June 2015; online 27 June 2015)

The title compound, C₁₈H₂₀N₂OS, displays whole-molecule disorder over two adjacent sets of sites with an occupancy ratio of 0.630 (11):0.370 (11). In each disorder component, the cyclohexyl ring shows a chair conformation with the exocyclic C—C bond in an equatorial orientation. The dihedral angles between the cyclohexyl 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 intramolecular 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 R²₂(8) loops for both components. Aromatic π–π stacking interactions [shortest centroid–centroid separation = 3.593 (9) Å] and a C—H⋯π interaction are also observed.

Keywords: crystal structure; whole-molecule disorder; thiourea derivatives; intramolecular N—H⋯O hydrogen bond; N—H⋯S hydrogen bonds; π–π stacking interactions; C—H⋯π interactions.

CCDC reference: 1408027

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₈H₂₀N₂OS
M_r = 312.42
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.219
S = 1.05
2945 reflections
404 parameters
1056 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C5/C10 ring.

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
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+2, -y+1, -z+1.

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 ).

Supporting information

CCDC reference: 1408027

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015011950/hb7448sup1.cif

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

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

checkCIF report

Comment top

The design and synthesis of thiourea are of considerable interest because of their use in agriculture, medicine and analytical chemistry (J·H. Hu et al., 2011). Thiourea derivatives are driven by their potential as biological active compounds (Sun et al., 2006) and in the material application such as anti corrosion (Shen et al., 2006). As part of our own studies in this area, the crystal structure of the title compound has been determined and the results are presented herein.

For the major disorder component, the cyclohexane ring (C13—C18) adopts chair conformation [puckering amplitudes and smallest displacement parameters are q = 0.568 Å, θ = 177.7 (8)°, ϕ = 19 (29)° and ΔC_s = 0.9 (14) Å]. Similarly, for the minor disorder component, the cyclohexane ring (C13^'—C18^') adopts a chair conformation. [puckering amplitudes and smallest displacement parameters are q = 0.56 (3) Å, θ = 180 (3)°, ϕ = 354 (31)° and ΔC_s = 3.0 (4) Å]. The dihedral angles between cyclohexane and benzene rings (C5—C8/C10) and (C5—C10) of naphthalene moiety are 37.0 (7)and 36.5 (7)° (major component). In the case of minor component, the dihedral angles between cyclohexane and benzene rings (C5—C8/C10)and (C5—C10) of naphthalene are 37.0 (7)and 36.5 (7)°, respectively. The molecular conformation is consolidated by an intramolecular N—H···O hydrogen bond, forming S(5) ring motif.

The crystal packing features N—H···S hydrogen bonds with the symmetry code: (i) 2 - x,-y,1 - z, which links the molecules into centrosymmetric dimers with graph-set descriptor of R²₂(8). The crystal packing also features C—H···π (Table 1) and π-π interactions (Cg2···Cg2ⁱⁱ = 3.593 (9) Å; Cg2 is the centroid of a ring C5—C10; symmetry code: (ii) 3 - x,1 - y,2 - z. The packing view of the title compound is shown in Fig. 3.

Related literature top

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 top

A solution of cyclohexane carbonyl chloride (1.4661 g, 10 mmol) in acetone (60 ml) was added drop wise to a suspension of potassium thiocyanate (0.9718 g, 10 mmol) in anhydrous acetone (60 ml). The reaction mixture was heated under reflux for 45 minutes and then cooled to room temperature. A solution of substituted naphthalen-1-amine (1.43 g, 10 mmol) in acetone (60 ml) was added and the resulting mixture was stirred for 2 h at room temperature. Hydrochloric acid (0.1 N, 500 ml) was added and the resulting white solid was filtered off, washed with water and dried in vaccum. The yield of the isolated product was 89%, giving colourless blocks.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the major component of the title compound, with displacement ellipsoids drawn at 40% probability level.
	Fig. 2. Stick plot of both major and minor components of the title compound, with the atoms label for non-H atoms.
	Fig. 3. 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).

N-[(Naphthalen-1-yl)carbamothioyl]cyclohexanecarboxamide top

Crystal data top

C₁₈H₂₀N₂OS	Z = 2
M_r = 312.42	F(000) = 332
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0972P)² + 1.1049P] where P = (F_o² + 2F_c²)/3
2945 reflections	(Δ/σ)_max = 0.053
404 parameters	Δρ_max = 0.87 e Å⁻³
1056 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₈H₂₀N₂OS	γ = 104.022 (3)°
M_r = 312.42	V = 835.24 (9) Å³
Triclinic, P1	Z = 2
a = 7.0464 (5) Å	Mo Kα radiation
b = 11.0379 (5) Å	µ = 0.20 mm⁻¹
c = 12.4151 (8) Å	T = 293 K
α = 110.873 (3)°	0.35 × 0.30 × 0.25 mm
β = 100.660 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2945 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1930 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.952	R_int = 0.031
14064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	1056 restraints
wR(F²) = 0.219	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.87 e Å⁻³
2945 reflections	Δρ_min = −0.25 e Å⁻³
404 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C5/C10 ring.

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

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C5/C10 ring.

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

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y+1, −z+1.

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection. JH thanks UGC for the fellowship.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gangadharan, R., Haribabu, J., Karvembu, R. & Sethusankar, K. (2015). Acta Cryst. E71, 305–308. CSD CrossRef IUCr Journals Google Scholar
Hu, J.-H., Luo, Z.-Y., Ding, C.-F. & Song, X.-L. (2011). Acta Cryst. E67, o376. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, C. B., Wang, S. G., Yang, H. Y., Long, K. & Wang, F. H. (2006). Corros. Sci. 48, 1655–1665. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, C., Huang, H., Feng, M., Shi, X., Zhang, X. & Zhou, P. (2006). Bioorg. Med. Chem. Lett. 16, 162–166. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 71| Part 7| July 2015| Pages o508-o509

doi:10.1107/S2056989015011950

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of N-[(naphthalen-1-yl)carbamo­thio­yl]cyclo­hexa­necarboxamide

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of N-[(naphthalen-1-yl)carbamothioyl]cyclohexanecarboxamide