N,N'-(Propane-1,3-di-yl)dibenzo-thio-amide.

The title compound, C17H18N2S2, exhibits a trans-trans-trans-gauche(+) (tttg (+)) conformation with regard to the NH-CH2-CH2-CH2-NH bond sequence. In the crystal, mol-ecules are connected by N-H⋯S=C and C-H⋯S=C hydrogen bonds, forming a herringbone arrangement along the c-axis direction. The two thioamide groups make dihedral angles of 43.0 (2) and 33.1 (2)° with the adjacent phenyl rings.

Related literature

For the crystal structures and conformations of related compounds, see: for example, Palmer & Brisse (1980 ▶); Brisson & Brisse (1986 ▶); Deguire & Brisse (1988 ▶); Nagasawa et al. (2014 ▶). For the synthesis, see: Hart & Brewbaker (1969 ▶); Cave & Levinson (1985 ▶).

Experimental

Crystal data

C17H18N2S2

M = 314.45

Orthorhombic,

a = 8.36521 (9) Å

b = 14.13395 (14) Å

c = 26.9223 (3) Å

V = 3183.12 (6) Å3

Z = 8

Cu Kα radiation

μ = 2.97 mm−1

T = 223 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEXII Ultra CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.47, T max = 0.76

12276 measured reflections

2882 independent reflections

2736 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.05

2882 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400974X/bv2233sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400974X/bv2233Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400974X/bv2233Isup3.cml

CCDC reference: 1000286

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

C17H18N2S2	F(000) = 1328
Mr = 314.45	Dx = 1.312 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
a = 8.36521 (9) Å	µ = 2.97 mm−1
b = 14.13395 (14) Å	T = 223 K
c = 26.9223 (3) Å	Prismatic, yellow
V = 3183.12 (6) Å3	0.30 × 0.20 × 0.10 mm
Z = 8

Bruker APEXII Ultra CCD area-detector diffractometer	2882 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	2736 reflections with I > 2σ(I)
Bruker Helios multilayer mirror monochromator	Rint = 0.018
Phi and ω scans	θmax = 68.3°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
Tmin = 0.47, Tmax = 0.76	k = −16→17
12276 measured reflections	l = −32→32

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0498P)2 + 1.0464P] where P = (Fo2 + 2Fc2)/3
2882 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. SADABS (Sheldrick 1996)

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 was performed with all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2, while the R-factor on F. The threshold expression of F2 > 2.0 σ(F2) was used only for calculating R-factor.

	x	y	z	Uiso*/Ueq
C1	0.04995 (15)	0.30766 (10)	0.42684 (5)	0.0271 (3)
C2	0.04043 (16)	0.33224 (9)	0.37326 (5)	0.0261 (3)
C3	0.15288 (18)	0.39267 (10)	0.35235 (5)	0.0328 (3)
H3	0.236	0.4175	0.3719	0.039*
C4	0.1418 (2)	0.41607 (11)	0.30247 (6)	0.0408 (4)
H4	0.2193	0.4555	0.288	0.049*
C5	0.0177 (2)	0.38189 (12)	0.27379 (6)	0.0435 (4)
H5	0.0109	0.3981	0.24	0.052*
C6	−0.0964 (2)	0.32377 (11)	0.29487 (6)	0.0400 (4)
H6	−0.1823	0.3017	0.2756	0.048*
C7	−0.08486 (17)	0.29786 (10)	0.34432 (5)	0.0318 (3)
H7	−0.1614	0.2572	0.3584	0.038*
C8	−0.00172 (17)	0.17921 (12)	0.48748 (6)	0.0380 (4)
H8A	−0.092	0.1351	0.487	0.046*
H8B	−0.0292	0.231	0.5101	0.046*
C9	0.14371 (17)	0.12807 (10)	0.50784 (5)	0.0340 (3)
H9A	0.2339	0.172	0.5108	0.041*
H9B	0.1747	0.0765	0.4855	0.041*
C10	0.09938 (18)	0.08896 (11)	0.55852 (6)	0.0364 (3)
H10A	0.0758	0.1419	0.5809	0.044*
H10B	0.0019	0.051	0.5553	0.044*
C11	0.19903 (16)	−0.02401 (9)	0.61993 (5)	0.0268 (3)
C12	0.33873 (16)	−0.07725 (9)	0.63952 (5)	0.0270 (3)
C13	0.34922 (18)	−0.09590 (10)	0.69027 (5)	0.0330 (3)
H13	0.2681	−0.0749	0.7118	0.04*
C14	0.4785 (2)	−0.14514 (12)	0.70912 (6)	0.0417 (4)
H14	0.4858	−0.1563	0.7435	0.05*
C15	0.5967 (2)	−0.17792 (12)	0.67788 (7)	0.0478 (4)
H15	0.6842	−0.2117	0.6908	0.057*
C16	0.5859 (2)	−0.16086 (13)	0.62749 (7)	0.0480 (4)
H16	0.6657	−0.1839	0.6061	0.058*
C17	0.45871 (19)	−0.11019 (11)	0.60823 (6)	0.0368 (3)
H17	0.4534	−0.098	0.5739	0.044*
N1	0.01881 (14)	0.21803 (9)	0.43765 (5)	0.0324 (3)
H1	0.0098	0.1789	0.4129	0.039*
N2	0.22457 (14)	0.03070 (8)	0.58067 (4)	0.0301 (3)
H2	0.3197	0.0319	0.5676	0.036*
S1	0.08969 (5)	0.39123 (3)	0.46914 (2)	0.03743 (13)
S2	0.01763 (4)	−0.03524 (3)	0.64602 (2)	0.03725 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0195 (6)	0.0338 (7)	0.0279 (7)	0.0044 (5)	−0.0002 (5)	0.0037 (5)
C2	0.0273 (6)	0.0256 (6)	0.0253 (6)	0.0051 (5)	0.0003 (5)	0.0011 (5)
C3	0.0312 (7)	0.0339 (7)	0.0333 (8)	0.0012 (6)	0.0037 (6)	0.0018 (5)
C4	0.0464 (9)	0.0401 (8)	0.0360 (8)	0.0058 (7)	0.0134 (7)	0.0093 (6)
C5	0.0620 (11)	0.0451 (9)	0.0235 (7)	0.0163 (8)	0.0029 (7)	0.0045 (6)
C6	0.0516 (9)	0.0382 (8)	0.0301 (7)	0.0063 (7)	−0.0113 (6)	−0.0039 (6)
C7	0.0360 (8)	0.0273 (6)	0.0320 (7)	0.0012 (5)	−0.0039 (6)	0.0008 (5)
C8	0.0310 (7)	0.0457 (9)	0.0372 (8)	0.0039 (6)	0.0028 (6)	0.0188 (7)
C9	0.0303 (7)	0.0361 (7)	0.0356 (8)	0.0006 (6)	−0.0008 (6)	0.0106 (6)
C10	0.0330 (8)	0.0413 (8)	0.0349 (8)	0.0058 (6)	−0.0007 (6)	0.0122 (6)
C11	0.0315 (7)	0.0231 (6)	0.0259 (6)	−0.0012 (5)	−0.0023 (5)	−0.0014 (5)
C12	0.0296 (7)	0.0233 (6)	0.0281 (6)	−0.0012 (5)	−0.0016 (5)	0.0010 (5)
C13	0.0391 (8)	0.0325 (7)	0.0275 (7)	0.0016 (6)	0.0002 (6)	0.0016 (5)
C14	0.0506 (9)	0.0427 (8)	0.0317 (8)	0.0055 (7)	−0.0086 (7)	0.0083 (7)
C15	0.0453 (9)	0.0478 (9)	0.0502 (10)	0.0152 (7)	−0.0079 (7)	0.0108 (8)
C16	0.0438 (9)	0.0545 (10)	0.0456 (9)	0.0193 (8)	0.0080 (7)	0.0056 (8)
C17	0.0412 (8)	0.0414 (8)	0.0279 (7)	0.0074 (7)	0.0028 (6)	0.0045 (6)
N1	0.0338 (6)	0.0338 (6)	0.0298 (6)	0.0025 (5)	−0.0009 (5)	0.0071 (5)
N2	0.0266 (6)	0.0323 (6)	0.0315 (6)	0.0001 (4)	−0.0015 (5)	0.0075 (5)
S1	0.0403 (2)	0.0455 (2)	0.0265 (2)	0.00085 (15)	−0.00578 (14)	−0.00393 (14)
S2	0.0315 (2)	0.0413 (2)	0.0390 (2)	0.00656 (14)	0.00747 (14)	0.00916 (15)

C1—N1	1.3256 (18)	C9—H9B	0.98
C1—C2	1.4860 (17)	C10—N2	1.4596 (18)
C1—S1	1.6741 (14)	C10—H10A	0.98
C2—C3	1.390 (2)	C10—H10B	0.98
C2—C7	1.393 (2)	C11—N2	1.3270 (17)
C3—C4	1.386 (2)	C11—C12	1.4867 (18)
C3—H3	0.94	C11—S2	1.6795 (14)
C4—C5	1.381 (3)	C12—C17	1.391 (2)
C4—H4	0.94	C12—C13	1.3942 (19)
C5—C6	1.381 (2)	C13—C14	1.382 (2)
C5—H5	0.94	C13—H13	0.94
C6—C7	1.384 (2)	C14—C15	1.379 (2)
C6—H6	0.94	C14—H14	0.94
C7—H7	0.94	C15—C16	1.381 (2)
C8—N1	1.4595 (18)	C15—H15	0.94
C8—C9	1.5175 (19)	C16—C17	1.383 (2)
C8—H8A	0.98	C16—H16	0.94
C8—H8B	0.98	C17—H17	0.94
C9—C10	1.518 (2)	N1—H1	0.87
C9—H9A	0.98	N2—H2	0.87
N1—C1—C2	115.21 (12)	N2—C10—C9	113.41 (12)
N1—C1—S1	124.33 (11)	N2—C10—H10A	108.9
C2—C1—S1	120.40 (10)	C9—C10—H10A	108.9
C3—C2—C7	119.80 (13)	N2—C10—H10B	108.9
C3—C2—C1	120.04 (12)	C9—C10—H10B	108.9
C7—C2—C1	120.11 (12)	H10A—C10—H10B	107.7
C4—C3—C2	119.58 (14)	N2—C11—C12	116.80 (12)
C4—C3—H3	120.2	N2—C11—S2	122.25 (10)
C2—C3—H3	120.2	C12—C11—S2	120.93 (10)
C5—C4—C3	120.58 (15)	C17—C12—C13	119.01 (13)
C5—C4—H4	119.7	C17—C12—C11	121.46 (12)
C3—C4—H4	119.7	C13—C12—C11	119.52 (12)
C4—C5—C6	119.84 (14)	C14—C13—C12	120.27 (14)
C4—C5—H5	120.1	C14—C13—H13	119.9
C6—C5—H5	120.1	C12—C13—H13	119.9
C5—C6—C7	120.29 (14)	C15—C14—C13	120.44 (14)
C5—C6—H6	119.9	C15—C14—H14	119.8
C7—C6—H6	119.9	C13—C14—H14	119.8
C6—C7—C2	119.87 (14)	C14—C15—C16	119.57 (14)
C6—C7—H7	120.1	C14—C15—H15	120.2
C2—C7—H7	120.1	C16—C15—H15	120.2
N1—C8—C9	114.63 (12)	C15—C16—C17	120.60 (15)
N1—C8—H8A	108.6	C15—C16—H16	119.7
C9—C8—H8A	108.6	C17—C16—H16	119.7
N1—C8—H8B	108.6	C16—C17—C12	120.09 (14)
C9—C8—H8B	108.6	C16—C17—H17	120.0
H8A—C8—H8B	107.6	C12—C17—H17	120.0
C8—C9—C10	107.59 (12)	C1—N1—C8	125.74 (13)
C8—C9—H9A	110.2	C1—N1—H1	117.1
C10—C9—H9A	110.2	C8—N1—H1	117.1
C8—C9—H9B	110.2	C11—N2—C10	122.59 (12)
C10—C9—H9B	110.2	C11—N2—H2	118.7
H9A—C9—H9B	108.5	C10—N2—H2	118.7

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2i	0.87	2.59	3.4412 (14)	168
N2—H2···S1ii	0.87	2.69	3.5135 (12)	157
C17—H17···S1iii	0.94	2.85	3.7665 (17)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2i	0.87	2.59	3.4412 (14)	168
N2—H2⋯S1ii	0.87	2.69	3.5135 (12)	157
C17—H17⋯S1iii	0.94	2.85	3.7665 (17)	166

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