N,N′-(Propane-1,3-di­yl)dibenzo­thio­amide

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

doi:10.1107/S160053681400974X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o639

doi:10.1107/S160053681400974X

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N,N′-(Propane-1,3-diyl)dibenzothioamide

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

Edited by R. J. Butcher, Howard University, USA (Received 5 April 2014; accepted 30 April 2014; online 3 May 2014)

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, molecules 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.

CCDC reference: 1000286

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_r = 314.45
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.05
2882 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) -x, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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: 1000286

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681400974X/bv2233sup1.cif

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

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

checkCIF report

Comment top

In a previous paper (Nagasawa et al., 2014), we reported the crystal structure of N, N'-(ethane-1,2-diyl)dibenzothioamide. In this study, we have determined the crystal structure of its homologue, N,N'-(propane-1,3-diyl)dibenzothioamide (referred to here as PDBTA), a monomeric model compound of poly(trimethylene terephthalthioamide), [–(C=S)–C₆H₄–(C=S)–NH–(CH₂)₃–NH–]_n. Figure 1 shows the molecular structure of PDBTA, whose NH–CH₂–CH₂–CH₂–NH bond sequence adopts the tttg⁺ conformation. On the other hand, our molecular orbital (MO) calculations at the B3LYP/6–311+G(2 d,p)//B3LYP/6–311+G(2 d,p) level including the solvent effect of dimethyl sulfoxide have predicted that the all-trans form is the most stable of its possible conformations; the crystal conformation, tttg⁺, was suggested to have a free energy higher than tttt by as much as 1.19 kcal mol^-1.

Figure 2 shows the molecular packing of the PDBTA crystal, in which two kinds of intermolecular hydrogen bonds, C=S···H–N and C=S···H–C, seem to be formed (not shown in the figure). For details, see Table 1. The intermolecular attractions may fully compensate the cost of conformational energy of 1.19 kcal mol^-1. The PDBTA molecules form a herringbone arrangement along the c-axis direction.

Brisson & Brisse (1986) determined the crystal structure of N,N'-(propane-1,3-diyl)dibenzamide (PDBA), a model compound of poly(trimethylene terephthalamide). The crystalline PDBA molecule lies in the ttg⁺g⁺ conformation and forms intermolecular C=O···H—N hydrogen bonds with the neighbors. According to our MO calculations, its most stable conformer is tttg⁺ (–0.54 kcal mol^-1 relative to that of the all-trans state), and the crystal conformation, ttg⁺g⁺, has a somewhat higher free energy (+0.32 kcal mol^-1).

Related literature top

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 top

Benzoyl chloride (12.0 ml, 103 mmol) was added dropwise to an aqueous solution of 1,3-diaminopropane (3.4 ml, 41 mmol) and sodium hydroxide (61.5 ml, 0.100 mol l^-1) stirred by a mechanical stirrer in a three-necked flask equipped with a dropping funnel and a calcium-chloride drying tube, with the flask being bathed in water kept at 10 °C. The mixture was stirred at 10 °C for 1 h, diluted with water (100 ml), and stirred again at room temperature overnight to yield white precipitate. The precipitate was collected by suction filtration, washed with water, and dried. The crude product was recrystallized from a mixture of ethanol and toluene (1:1 in volume) and dried at 40 °C under reduced pressure to yield PDBA (yield 28%). In principle, this synthesis is based on the procedure of Hart & Brewbaker (1969).

PDBA (1.0 g, 3.6 mmol) and Lawesson's reagent (1.7 g, 4.2 mmol) (Cave & Levinson, 1985) 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 mixture was refluxed under dry nitrogen at ca 110 °C for 8 h, and the completion of the reaction was confirmed by thin-layer chromatography. After toluene was removed under reduced pressure, the residual was subjected to column chromatography on silica gel with chloroform, and yellowish solution (retention factor R_f = 0.3) was collected and condensed to yield yellow slurry, which was recrystallized twice from a mixture of ethyl acetate and diethyl ether (1:1 in volume) and dried under reduced pressure to yield PDBTA (yield 48%).

A small quantity of PDBTA 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, crystals were found to be formed suitable for X-ray diffraction.

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 N, N'-(propane-1,2-diyl)dibenzothioamide (PDBTA). 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 diagram of PDBTA, viewed down the (a) a, (b) b, and (c) c axes.

N,N'-(Propane-1,3-diyl)dibenzothioamide top

Crystal data top

C₁₇H₁₈N₂S₂	F(000) = 1328
M_r = 314.45	D_x = 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

Data collection top

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	R_int = 0.018
Phi and ω scans	θ_max = 68.3°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
T_min = 0.47, T_max = 0.76	k = −16→17
12276 measured reflections	l = −32→32

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0498P)² + 1.0464P] where P = (F_o² + 2F_c²)/3
2882 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₇H₁₈N₂S₂	V = 3183.12 (6) Å³
M_r = 314.45	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 8.36521 (9) Å	µ = 2.97 mm⁻¹
b = 14.13395 (14) Å	T = 223 K
c = 26.9223 (3) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker APEXII Ultra CCD area-detector diffractometer	2882 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2736 reflections with I > 2σ(I)
T_min = 0.47, T_max = 0.76	R_int = 0.018
12276 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
2882 reflections	Δρ_min = −0.31 e Å⁻³
190 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

References

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Volume 70| Part 6| June 2014| Page o639

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