N,N′-(Ethane-1,2-di­yl)di­benzene­carbo­thio­amide

Nagasawa, M.; Sasanuma, Y.; Masu, H.

doi:10.1107/S1600536814008368

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o586

doi:10.1107/S1600536814008368

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N,N′-(Ethane-1,2-diyl)dibenzenecarbothioamide

Masayuki Nagasawa,^a Yuji Sasanuma ^a ^* and Hyuma Masu ^b

^aDepartment of Applied Chemistry and Biotechnology, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan, and ^bCenter for Analytical Instrumentation, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
^*Correspondence e-mail: sasanuma@faculty.chiba-u.jp

(Received 5 April 2014; accepted 14 April 2014; online 18 April 2014)

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

CCDC reference: 997112

Related literature

For crystal structures and conformations of related compounds with –(C=X)–C₆H₄–(C=X)–Y–(CH₂)_m–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_r = 300.43
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.083
S = 1.04
2763 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1.

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.

Supporting information

CCDC reference: 997112

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814008368/is5357sup1.cif

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

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

checkCIF report

Comment top

In our previous studies, conformational characteristics and configurational properties of aromatic polythioesters (X = O and Y = S) and polydithioesters (X = Y = S) (Abe & Sasanuma, 2012) expressed as [–(C=X)–C₆H₄–(C=X)–Y–(CH₂)_m–Y–]_n were investigated through molecular orbital (MO) calculations and NMR and single-crystal X-ray diffraction experiments on their model compounds (Abe et al., 2011; Abe & Sasanuma, 2013). The theoretical and experimental data thus obtained were applied to the ab initio statistical mechanics to derive bond conformations, configurational properties, and thermodynamic quantities on the target polymers. In the present study, we have treated aromatic polyamides (X = O and Y = NH), polythioamides (X = S and Y = NH), and their model compounds, C₆H₅–(C=X)–NH–(CH₂)_m–NH–(C=X)–C₆H₅. Crystal structures of the model compounds (X = O and m = 2 and 3) of poly(ethylene terephthalamide) and poly(trimethylene terephthalamide) were already determined (Palmer & Brisse, 1980; Brisson & Brisse, 1986). This paper reports the crystal structure of N,N'-(ethane-1,2-diyl)benzenecarbothioamide (X = S and m = 2, referred to hereafter as EDBTA) corresponding to the model compound of poly(ethylene terephthalthioamide).

Figure 1 shows the molecular structure of EDBTA, whose NH–CH₂–CH₂–NH bonds adopt the g⁺g⁺g⁺ conformation. The MO calculations at the B3LYP/6–311+G(2d,p)//B3LYP/6–311+G(2d,p) level including the solvent effect of dimethyl sulfoxide have predicted conformational preferences of EDBTA; the first and second most stable conformers are tg⁺g^– (–0.99) and g⁺g⁺g⁺ (–0.76), respectively, where the values in the parentheses are Gibbs free energies in kcal mol^–1 relative to that of the all-trans state.

According to the MO calculations, the tg⁺g^– conformer of EDBTA seems to form intramolecular C=S···H–N and C=S···C–H attractions. As shown in Figure 2, the crystallized EDBTA molecule, lying in the g⁺g⁺g⁺ conformation, forms intermolecular C=S···H–N and C–H..π interactions. Probably, the crystalline EDBTA chooses the intermolecular C=S···H–N interaction rather than the intramolecular one to acquire a larger energy stability. The MO calculations predicted that stable conformers of N,N'-(ethane-1,2-diyl)dibenzamide (X = O and m =2, abbreviated as EDBA), the model compound of poly(ethylene terephthalamide), are, in the ascending order of free energy, tg⁺g^–, g⁺tg⁺, g⁺g⁺g⁺, g⁺tg^–,···; the energy difference between g⁺tg^– and tg⁺g^– was estimated as 0.89 kcal mol^-1. Nevertheless, the EDBA molecule crystallizes to adopt the fourth stable conformation, g⁺tg^– (Palmer & Brisse, 1980). In contrast with models of the polythioester (X = O, Y = S, and m = 2) and polydithioester (X = Y = S and m = 2) (Abe et al., 2011; Abe & Sasanuma, 2012), EDBA and EDBTA do not crystallize in the most stable conformation suggested by the MO calculations probably because of the significant stabilization of the intermolecular C=O···H—N and C=S···H—N hydrogen bonds.

Related literature top

For crystal structures and conformations of related compounds with –(C═ X)–C₆H₄–(C═X)–Y–(CH₂)_m–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 top

Benzoyl chloride (4.6 ml, 40 mmol), dissolved in 1,2-dichloroethane (100 ml), was added dropwise to ethylenediamine (14 ml, 210 mmol) and 1,2-dichloroethane (300 ml) stirred by a magnetic stirrer in a three-necked flask equipped with a dropping funnel and a calcium-chloride drying tube, with the flask being bathed in ice water. The mixture was stirred at room temperature for 8 h to yield white precipitate. The precipitate was collected by suction filtration, washed with water, and dried. The crude product was recrystallized from methanol and dried at 40 °C under reduced pressure to yield EDBA (yield 55%). In principle, this synthesis is based on the procedure of Jacobson et al. (1987).

Lawesson's reagent (1.8 g, 4.6 mmol) and EDBA (1.0 g, 3.7 mmol) were dissolved in toluene (20 ml) stirred in a three-necked flask equipped with a reflux condenser connected to a calcium-chloride drying tube. The solution was refluxed under dry nitrogen at ca 110 °C for 8 h to yield yellow precipitate. The precipitate was collected, washed with toluene, recrystallized from ethanol, and dried at 40 °C under reduced pressure to yield EDBTA (yield 79%).

A small quantity of EDBTA was dissolved in chloroform in a glass tube, whose top was sealed with a thin Teflon film. The tube was placed in a vial container including a small amount of n-hexane, and the container was capped and left to stand still in a dark place. After a day, its crystals were found to be formed in the inner tube.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Isotropic H-atom thermal parameters are represented by spheres of arbitrary size. The labels of hydrogen atoms are omitted for clarity.
	Fig. 2. Packing diagrams of the title compound, viewed down the (a) a and (b) b axes. The dotted lines represent C=S···H—N and C—H···π interactions.

N,N'-(Ethane-1,2-diyl)dibenzenecarbothioamide top

Crystal data top

C₁₆H₁₆N₂S₂	V = 780.67 (2) Å³
M_r = 300.43	Z = 2
Triclinic, P1	F(000) = 316
a = 8.6652 (1) Å	D_x = 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

Data collection top

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	R_int = 0.014
ϕ and ω scans	θ_max = 68.2°, θ_min = 4.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.58, T_max = 0.86	k = −11→11
10280 measured reflections	l = −10→12

Refinement top

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(F_o²) + (0.0481P)² + 0.2337P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2763 reflections	Δρ_max = 0.28 e Å⁻³
181 parameters	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₆N₂S₂	γ = 101.5370 (6)°
M_r = 300.43	V = 780.67 (2) Å³
Triclinic, P1	Z = 2
a = 8.6652 (1) Å	Cu Kα radiation
b = 9.4596 (1) Å	µ = 3.01 mm⁻¹
c = 10.3457 (1) Å	T = 223 K
α = 105.5452 (7)°	0.20 × 0.05 × 0.05 mm
β = 98.9293 (7)°

Data collection top

Bruker APEXII Ultra CCD area-detector diffractometer	2763 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2568 reflections with I > 2σ(I)
T_min = 0.58, T_max = 0.86	R_int = 0.014
10280 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.04	Δρ_max = 0.28 e Å⁻³
2763 reflections	Δρ_min = −0.18 e Å⁻³
181 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 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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.

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Volume 70| Part 5| May 2014| Page o586

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