N,N'-(Ethane-1,2-di-yl)di-benzene-carbo-thio-amide.

The title compound, C16H16N2S2, adopts a gauche (+)-gauche (+)-gauche (+) (g(+)g(+)g(+) ) conformation in the NH-CH2-CH2-NH bond sequence. In the crystal, mol-ecules are connected by pairs of N-H⋯S=C hydrogen bonds and C-H⋯π inter-actions, forming a tape structure along the c-axis direction.

Related literature

For crystal structures and conformations of related compounds with –(C=X)–C6H4–(C=X)–Y–(CH2)–Y– (X = O or S and Y = O, S, or NH) bond sequences, see for example,: Palmer & Brisse (1980 ▶); Brisson & Brisse (1986 ▶); Abe et al. (2011 ▶); Abe & Sasanuma (2012 ▶, 2013 ▶). For the synthesis, see: Jacobson et al. (1987 ▶).

Experimental

Crystal data

C16H16N2S2

M = 300.43

Triclinic,

a = 8.6652 (1) Å

b = 9.4596 (1) Å

c = 10.3457 (1) Å

α = 105.5452 (7)°

β = 98.9293 (7)°

γ = 101.5370 (6)°

V = 780.67 (2) Å3

Z = 2

Cu Kα radiation

μ = 3.01 mm−1

T = 223 K

0.20 × 0.05 × 0.05 mm

Data collection

Bruker APEXII Ultra CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.58, T max = 0.86

10280 measured reflections

2763 independent reflections

2568 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.083

S = 1.04

2763 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536814008368/is5357sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008368/is5357Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008368/is5357Isup3.cml

CCDC reference: 997112

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

C16H16N2S2	V = 780.67 (2) Å3
Mr = 300.43	Z = 2
Triclinic, P1	F(000) = 316
a = 8.6652 (1) Å	Dx = 1.278 Mg m−3
b = 9.4596 (1) Å	Cu Kα radiation, λ = 1.54178 Å
c = 10.3457 (1) Å	µ = 3.01 mm−1
α = 105.5452 (7)°	T = 223 K
β = 98.9293 (7)°	Needle, yellow
γ = 101.5370 (6)°	0.20 × 0.05 × 0.05 mm

Bruker APEXII Ultra CCD area-detector diffractometer	2763 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	2568 reflections with I > 2σ(I)
Bruker Helios multilayer mirror monochromator	Rint = 0.014
φ and ω scans	θmax = 68.2°, θmin = 4.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.58, Tmax = 0.86	k = −11→11
10280 measured reflections	l = −10→12

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.2337P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2763 reflections	Δρmax = 0.28 e Å−3
181 parameters	Δρmin = −0.18 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 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	0.55284 (15)	0.70259 (14)	0.66245 (14)	0.0269 (3)
C2	0.39798 (16)	0.74362 (15)	0.62755 (14)	0.0267 (3)
C3	0.25373 (17)	0.65794 (16)	0.63997 (14)	0.0306 (3)
H3	0.2543	0.5762	0.6752	0.037*
C4	0.10937 (17)	0.69267 (17)	0.60064 (16)	0.0356 (3)
H4	0.0121	0.6341	0.6086	0.043*
C5	0.10820 (18)	0.81363 (18)	0.54961 (16)	0.0373 (3)
H5	0.0101	0.8369	0.5226	0.045*
C6	0.25101 (18)	0.90021 (18)	0.53830 (17)	0.0379 (3)
H6	0.2501	0.9829	0.5044	0.046*
C7	0.39529 (17)	0.86538 (16)	0.57682 (15)	0.0325 (3)
H7	0.4922	0.9244	0.5687	0.039*
C8	0.71343 (18)	0.60757 (18)	0.82305 (15)	0.0353 (3)
H8A	0.7237	0.6194	0.9213	0.042*
H8B	0.8119	0.6707	0.8121	0.042*
C9	0.69808 (19)	0.44220 (18)	0.74548 (16)	0.0374 (3)
H9A	0.7012	0.4325	0.6493	0.045*
H9B	0.7903	0.4104	0.7855	0.045*
C10	0.52445 (19)	0.29310 (17)	0.85582 (15)	0.0360 (3)
C11	0.35708 (19)	0.20806 (17)	0.84557 (15)	0.0363 (3)
C12	0.2252 (2)	0.25356 (18)	0.79138 (16)	0.0400 (4)
H12	0.2417	0.3354	0.7556	0.048*
C13	0.0696 (2)	0.1792 (2)	0.78978 (18)	0.0504 (4)
H13	−0.0187	0.2121	0.7548	0.06*
C14	0.0438 (2)	0.0564 (2)	0.8396 (2)	0.0569 (5)
H14	−0.0618	0.0058	0.8383	0.068*
C15	0.1734 (3)	0.0089 (2)	0.89112 (19)	0.0553 (5)
H15	0.1559	−0.0756	0.9235	0.066*
C16	0.3285 (2)	0.08408 (19)	0.89556 (17)	0.0453 (4)
H16	0.4162	0.0517	0.9326	0.054*
N1	0.57488 (14)	0.66031 (14)	0.77434 (12)	0.0312 (3)
H1	0.5012	0.6642	0.8226	0.037*
N2	0.54942 (16)	0.34276 (14)	0.75044 (12)	0.0361 (3)
H2	0.4702	0.3133	0.6785	0.043*
S1	0.68758 (4)	0.70858 (4)	0.56244 (4)	0.03447 (12)
S2	0.67017 (5)	0.32702 (6)	0.99595 (4)	0.04788 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0259 (6)	0.0285 (6)	0.0259 (7)	0.0067 (5)	0.0055 (5)	0.0083 (5)
C2	0.0270 (6)	0.0306 (6)	0.0236 (7)	0.0092 (5)	0.0072 (5)	0.0080 (5)
C3	0.0319 (7)	0.0325 (7)	0.0311 (8)	0.0095 (6)	0.0100 (6)	0.0130 (6)
C4	0.0262 (7)	0.0414 (8)	0.0396 (9)	0.0069 (6)	0.0104 (6)	0.0125 (6)
C5	0.0299 (7)	0.0492 (9)	0.0379 (9)	0.0186 (6)	0.0074 (6)	0.0154 (7)
C6	0.0407 (8)	0.0415 (8)	0.0422 (9)	0.0190 (7)	0.0127 (7)	0.0220 (7)
C7	0.0303 (7)	0.0356 (7)	0.0366 (8)	0.0092 (6)	0.0116 (6)	0.0164 (6)
C8	0.0350 (7)	0.0483 (8)	0.0265 (8)	0.0169 (6)	0.0040 (6)	0.0146 (6)
C9	0.0429 (8)	0.0509 (9)	0.0288 (8)	0.0240 (7)	0.0129 (6)	0.0176 (6)
C10	0.0488 (9)	0.0408 (8)	0.0268 (8)	0.0243 (7)	0.0112 (6)	0.0129 (6)
C11	0.0507 (9)	0.0385 (8)	0.0238 (8)	0.0186 (7)	0.0097 (6)	0.0102 (6)
C12	0.0493 (9)	0.0439 (8)	0.0310 (8)	0.0175 (7)	0.0090 (7)	0.0142 (6)
C13	0.0482 (10)	0.0628 (11)	0.0392 (10)	0.0172 (8)	0.0077 (7)	0.0128 (8)
C14	0.0600 (11)	0.0595 (11)	0.0434 (11)	0.0015 (9)	0.0154 (8)	0.0110 (8)
C15	0.0809 (14)	0.0453 (9)	0.0417 (10)	0.0100 (9)	0.0196 (9)	0.0175 (8)
C16	0.0657 (11)	0.0440 (9)	0.0324 (9)	0.0218 (8)	0.0114 (7)	0.0158 (7)
N1	0.0325 (6)	0.0418 (6)	0.0256 (6)	0.0160 (5)	0.0096 (5)	0.0140 (5)
N2	0.0444 (7)	0.0439 (7)	0.0251 (6)	0.0188 (6)	0.0073 (5)	0.0138 (5)
S1	0.02655 (19)	0.0504 (2)	0.0359 (2)	0.01414 (15)	0.01281 (14)	0.02216 (16)
S2	0.0469 (2)	0.0748 (3)	0.0317 (2)	0.0247 (2)	0.00711 (17)	0.0264 (2)

C1—N1	1.3216 (17)	C9—H9A	0.98
C1—C2	1.4882 (18)	C9—H9B	0.98
C1—S1	1.6783 (13)	C10—N2	1.3278 (19)
C2—C7	1.3906 (19)	C10—C11	1.484 (2)
C2—C3	1.3915 (19)	C10—S2	1.6791 (15)
C3—C4	1.384 (2)	C11—C12	1.390 (2)
C3—H3	0.94	C11—C16	1.397 (2)
C4—C5	1.384 (2)	C12—C13	1.386 (2)
C4—H4	0.94	C12—H12	0.94
C5—C6	1.381 (2)	C13—C14	1.385 (3)
C5—H5	0.94	C13—H13	0.94
C6—C7	1.382 (2)	C14—C15	1.376 (3)
C6—H6	0.94	C14—H14	0.94
C7—H7	0.94	C15—C16	1.377 (3)
C8—N1	1.4598 (17)	C15—H15	0.94
C8—C9	1.523 (2)	C16—H16	0.94
C8—H8A	0.98	N1—H1	0.87
C8—H8B	0.98	N2—H2	0.87
C9—N2	1.452 (2)
N1—C1—C2	115.89 (11)	N2—C9—H9B	109.2
N1—C1—S1	123.18 (10)	C8—C9—H9B	109.2
C2—C1—S1	120.93 (10)	H9A—C9—H9B	107.9
C7—C2—C3	119.15 (12)	N2—C10—C11	116.16 (13)
C7—C2—C1	119.98 (12)	N2—C10—S2	122.96 (13)
C3—C2—C1	120.82 (12)	C11—C10—S2	120.86 (11)
C4—C3—C2	120.26 (13)	C12—C11—C16	118.40 (16)
C4—C3—H3	119.9	C12—C11—C10	120.86 (13)
C2—C3—H3	119.9	C16—C11—C10	120.69 (14)
C5—C4—C3	120.02 (13)	C13—C12—C11	120.52 (15)
C5—C4—H4	120.0	C13—C12—H12	119.7
C3—C4—H4	120.0	C11—C12—H12	119.7
C6—C5—C4	120.08 (13)	C14—C13—C12	120.19 (17)
C6—C5—H5	120.0	C14—C13—H13	119.9
C4—C5—H5	120.0	C12—C13—H13	119.9
C5—C6—C7	120.05 (13)	C15—C14—C13	119.69 (18)
C5—C6—H6	120.0	C15—C14—H14	120.2
C7—C6—H6	120.0	C13—C14—H14	120.2
C6—C7—C2	120.42 (13)	C14—C15—C16	120.44 (17)
C6—C7—H7	119.8	C14—C15—H15	119.8
C2—C7—H7	119.8	C16—C15—H15	119.8
N1—C8—C9	112.27 (12)	C15—C16—C11	120.74 (16)
N1—C8—H8A	109.1	C15—C16—H16	119.6
C9—C8—H8A	109.1	C11—C16—H16	119.6
N1—C8—H8B	109.1	C1—N1—C8	124.96 (12)
C9—C8—H8B	109.1	C1—N1—H1	117.5
H8A—C8—H8B	107.9	C8—N1—H1	117.5
N2—C9—C8	112.14 (12)	C10—N2—C9	125.36 (13)
N2—C9—H9A	109.2	C10—N2—H2	117.3
C8—C9—H9A	109.2	C9—N2—H2	117.3
N1—C1—C2—C7	140.90 (14)	S2—C10—C11—C16	−38.65 (19)
S1—C1—C2—C7	−39.89 (17)	C16—C11—C12—C13	1.3 (2)
N1—C1—C2—C3	−41.60 (18)	C10—C11—C12—C13	−176.08 (15)
S1—C1—C2—C3	137.61 (12)	C11—C12—C13—C14	−1.4 (3)
C7—C2—C3—C4	0.8 (2)	C12—C13—C14—C15	0.2 (3)
C1—C2—C3—C4	−176.74 (13)	C13—C14—C15—C16	1.1 (3)
C2—C3—C4—C5	−0.4 (2)	C14—C15—C16—C11	−1.2 (3)
C3—C4—C5—C6	−0.2 (2)	C12—C11—C16—C15	0.0 (2)
C4—C5—C6—C7	0.6 (2)	C10—C11—C16—C15	177.37 (15)
C5—C6—C7—C2	−0.2 (2)	C2—C1—N1—C8	176.47 (13)
C3—C2—C7—C6	−0.5 (2)	S1—C1—N1—C8	−2.7 (2)
C1—C2—C7—C6	177.09 (13)	C9—C8—N1—C1	−79.82 (18)
N1—C8—C9—N2	−55.40 (17)	C11—C10—N2—C9	172.70 (13)
N2—C10—C11—C12	−39.7 (2)	S2—C10—N2—C9	−5.6 (2)
S2—C10—C11—C12	138.62 (13)	C8—C9—N2—C10	−79.40 (17)
N2—C10—C11—C16	143.00 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2i	0.87	2.56	3.4186 (13)	168
N2—H2···S1ii	0.87	2.58	3.4097 (13)	159
C8—H8A···Cg2i	0.99	2.78	3.5376 (17)	134
C9—H9A···Cg1i	0.99	2.87	3.6685 (17)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C11–C16 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2i	0.87	2.56	3.4186 (13)	168
N2—H2⋯S1ii	0.87	2.58	3.4097 (13)	159
C8—H8A⋯Cg2i	0.99	2.78	3.5376 (17)	134
C9—H9A⋯Cg1i	0.99	2.87	3.6685 (17)	140

Symmetry codes: (i) ; (ii) .