Crystal structure of N,N′-bis­(4-methyl­phen­yl)di­thio­oxamide

Giannetto, A.; Lanza, S.; Bruno, G.; Nicoló, F.; Amiri Rudbari, H.

doi:10.1107/S2056989014027911

organic compounds

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Volume 71| Part 2| February 2015| Page o67

doi:10.1107/S2056989014027911

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Crystal structure of N,N′-bis(4-methylphenyl)dithiooxamide

Antonino Giannetto,^a ^* Santo Lanza,^a Giuseppe Bruno,^a Francesco Nicoló ^a and Hadi Amiri Rudbari ^b

^aDepartment of Chemical Sciences, University of Messina, Via F. Stagno d'Alcontres 31, 98166 Messina, Italy, and ^bDepartment of Chemistry, University of Isfahan, 81746-73441 Isfahan, Iran
^*Correspondence e-mail: giannettoa@unime.it

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 11 December 2014; accepted 22 December 2014; online 3 January 2015)

Two half molecules of the title compound, C₁₆H₁₆N₂S₂, are present in the asymmetric unit and both molecules are completed by crystallographic inversion centers at the mid-points of the central C—C bonds: the lengths of these bonds [1.538 (5) and 1.533 (5) Å] indicate negligible electronic delocalization. The trans-dithiooxamide fragment in each molecule is characterized by a pair of intramolecular N—H⋯S hydrogen bonds. In the crystal, molecules are linked by weak C—H..π interactions, generating a three-dimensional network.

Keywords: crystal structure; dithiooxamide; ethanedithioamide; intramolecular N—H⋯S hydrogen bonds; C—H..π interactions.

CCDC reference: 1040609

1. Related literature

For the mesogenic properties of related compounds, see: Aversa et al. (1997 , 2000 ). For the general procedure for the preparation of secondary and tertiary dithiooxamides, see: Lanza et al. (1993 , 2000 , 2003 ); Rosace et al. (1993 ). For similar crystal structures, see: Shimanouchi & Sasada (1979 ).

2. Experimental

2.1. Crystal data

C₁₆H₁₆N₂S₂
M_r = 300.43
Monoclinic, C 2/c
a = 33.9423 (7) Å
b = 11.3880 (2) Å
c = 7.8049 (2) Å
β = 99.439 (1)°
V = 2976.02 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 K
0.15 × 0.10 × 0.08 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: integration (SADABS; Bruker, 2012 ) T_min = 0.657, T_max = 0.745
45528 measured reflections
2621 independent reflections
1626 reflections with I > 2σ(I)
R_int = 0.066

2.3. Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.152
S = 1.11
2621 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.86	2.35	2.904 (3)	122
N2—H2⋯S2ⁱⁱ	0.86	2.35	2.901 (3)	122
C7—H7⋯Cg1ⁱⁱⁱ	0.93	2.90	3.587 (3)	132
C11—H11⋯Cg1^iv	0.93	2.77	3.524 (3)	139
C14—H14⋯Cg2^v	0.93	2.88	3.654 (3)	142
Symmetry codes: (i) -x+2, -y+2, -z; (ii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[x, -y+2, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1040609

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989014027911/hb7339sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989014027911/hb7339Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989014027911/hb7339Isup3.cml

checkCIF report

Comment top

Aryl-substituted secondary dithiooxamides H₂N₂C₂S₂R₂ (R=-C₆H₄X, C₆H₃X₂, X =-O-(CH₂)_n-CH₃, 7 <n > 11) have been exploited to prepare platinum(II) complexes which exhibit mesogenic properties (Aversa, et al. 1997; Aversa, et al. 2000). The title compound has been synthesized for a better understanding of the reactivity of the said mesogenic complexes, in the aim to avoid contingent steric hindrance of long chain substituents and the influence on the acid base equilibria of ether moieties. In fact, both the oxygen lone pairs in ether moieties and the exceedingly long alkyl chains of X substituents prevents the formation of ion pairs in the first step of the reaction of secondary dithioxamides with cis-Pt(Me₂SO)₂Cl₂ (Lanza et al., 1993). A detailed analysis of the bond distances reveals a strong double-bond character for both C—S and C—N [1.662 (3) Å and 1.318 (4) Å, respectively], confirming that the important electronic π-delocalization of the N—C—S system does not affect the central C—C bond. In the title compound the central C—C bond distances are 1.538 (5) Å and 1.533 (5) Å respectively for C1—C1' and C9—C9'. Going from a secondary dithiooxamide to a tertiary one we observe a large changing in structural parameters:essentially in the planarity loss of the central fragment and to the significant shortening of central C—C bond. The p-tolyl groups are rotated by -36.4° (5) and -35.4° (5) with respect to the central DTO fragments.

Related literature top

For the mesogenic properties of related compounds, see: Aversa et al. (1997, 2000). For the general procedure for the preparation of secondary and tertiary dithiooxamides, see: Lanza et al. (1993, 2000, 2003); Rosace et al. (1993). For similar crystal structures, see: Shimanouchi & Sasada (1979).

Experimental top

The title compound was obtained from para-toluidine according to a described two-step strategy based on primary amine reaction with oxalyl chloride followed by P₂S₅ treatment. ¹H NMR: δ 12.33 (bs, NH), 7.92 (d, J_ortho 8.4 Hz, H_2,6), 7.28 (d, H_3,5), 2.40 (s, Me). ¹³CNMR: δ 180.56 (CS), 137,75 (C₄), 135.80 (C₁), 129.64 (C_3,5), 122.17 (C_2,6), 21.27 (Me)

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title molecule with displacement ellipsoids plotted at the 50% probability level, while H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Packing diagram of the title compound viewed along the c axis.
	Fig. 3. Packing diagram of the title compound viewed normal the b axis and showing molecular arrangement on the (402) plane.

N,N'-Bis(4-methylphenyl)ethanedithioamide top

Crystal data top

C₁₆H₁₆N₂S₂	F(000) = 1264
M_r = 300.43	D_x = 1.341 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 141 reflections
a = 33.9423 (7) Å	θ = 4.3–22.0°
b = 11.3880 (2) Å	µ = 0.35 mm⁻¹
c = 7.8049 (2) Å	T = 293 K
β = 99.439 (1)°	Prismatic, orange
V = 2976.02 (11) Å³	0.15 × 0.10 × 0.08 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	2621 independent reflections
Radiation source: fine-focus sealed tube	1626 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.2°
Absorption correction: integration (SADABS; Bruker, 2012)	h = −40→40
T_min = 0.657, T_max = 0.745	k = −13→13
45528 measured reflections	l = −9→9

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.078P)² + 1.595P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
2621 reflections	Δρ_max = 1.03 e Å⁻³
181 parameters	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₁₆N₂S₂	V = 2976.02 (11) Å³
M_r = 300.43	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.9423 (7) Å	µ = 0.35 mm⁻¹
b = 11.3880 (2) Å	T = 293 K
c = 7.8049 (2) Å	0.15 × 0.10 × 0.08 mm
β = 99.439 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2621 independent reflections
Absorption correction: integration (SADABS; Bruker, 2012)	1626 reflections with I > 2σ(I)
T_min = 0.657, T_max = 0.745	R_int = 0.066
45528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.11	Δρ_max = 1.03 e Å⁻³
2621 reflections	Δρ_min = −0.21 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.99746 (3)	0.81087 (8)	0.00428 (12)	0.0493 (3)
N1	0.94997 (8)	0.9912 (2)	−0.1064 (3)	0.0362 (7)
H1	0.9486	1.0665	−0.115	0.043*
C1	0.98496 (9)	0.9507 (3)	−0.0303 (4)	0.0325 (7)
C2	0.91413 (10)	0.9314 (3)	−0.1764 (4)	0.0319 (8)
C3	0.91366 (10)	0.8248 (3)	−0.2619 (4)	0.0376 (8)
H3	0.9375	0.7876	−0.2728	0.045*
C4	0.87745 (10)	0.7739 (3)	−0.3311 (4)	0.0341 (8)
H4	0.8773	0.7022	−0.3883	0.041*
C5	0.84155 (10)	0.8273 (3)	−0.3169 (4)	0.0329 (8)
C6	0.84256 (10)	0.9343 (3)	−0.2318 (4)	0.0347 (8)
H6	0.8187	0.9716	−0.221	0.042*
C7	0.87853 (10)	0.9868 (3)	−0.1626 (4)	0.0335 (8)
H7	0.8787	1.0591	−0.107	0.04*
C8	0.80238 (11)	0.7709 (4)	−0.3933 (5)	0.0527 (11)
H8A	0.7807	0.8197	−0.371	0.079*	0.5
H8B	0.8004	0.6952	−0.3411	0.079*	0.5
H8C	0.8011	0.7618	−0.5164	0.079*	0.5
H8D	0.8074	0.6981	−0.448	0.079*	0.5
H8E	0.7878	0.8226	−0.4779	0.079*	0.5
H8F	0.787	0.756	−0.3026	0.079*	0.5
S2	0.74804 (3)	0.06064 (8)	0.49865 (14)	0.0539 (3)
C9	0.73490 (9)	0.2010 (3)	0.4708 (4)	0.0317 (7)
C10	0.66362 (9)	0.1808 (3)	0.3324 (4)	0.0298 (7)
C11	0.62785 (10)	0.2328 (3)	0.3544 (4)	0.0298 (7)
H11	0.628	0.3029	0.4157	0.036*
C12	0.59213 (10)	0.1807 (3)	0.2856 (4)	0.0350 (8)
H12	0.5683	0.2158	0.3016	0.042*
C13	0.59114 (10)	0.0767 (3)	0.1928 (4)	0.0349 (8)
C14	0.62709 (11)	0.0269 (3)	0.1714 (4)	0.0383 (9)
H14	0.6269	−0.0427	0.1088	0.046*
C15	0.66335 (10)	0.0771 (3)	0.2398 (4)	0.0351 (8)
H15	0.6872	0.0417	0.2239	0.042*
C16	0.55213 (12)	0.0194 (4)	0.1170 (5)	0.0542 (11)
H16A	0.5304	0.0656	0.1446	0.081*	0.5
H16B	0.551	−0.0579	0.1649	0.081*	0.5
H16C	0.5502	0.014	−0.0069	0.081*	0.5
H16D	0.5573	−0.0512	0.0572	0.081*	0.5
H16E	0.5367	0.0724	0.0368	0.081*	0.5
H16F	0.5375	0.0005	0.2086	0.081*	0.5
N2	0.69939 (8)	0.2412 (2)	0.4032 (3)	0.0345 (7)
H2	0.6974	0.3165	0.4014	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0357 (5)	0.0427 (6)	0.0649 (6)	−0.0054 (4)	−0.0051 (4)	0.0079 (4)
N1	0.0268 (17)	0.0327 (16)	0.0462 (16)	−0.0045 (13)	−0.0025 (13)	0.0003 (12)
C1	0.0267 (16)	0.0429 (18)	0.0283 (15)	−0.0072 (15)	0.0052 (12)	0.0001 (14)
C2	0.0230 (17)	0.039 (2)	0.0318 (16)	−0.0040 (16)	−0.0003 (13)	0.0034 (15)
C3	0.0277 (18)	0.045 (2)	0.0396 (18)	0.0023 (17)	0.0048 (14)	−0.0032 (16)
C4	0.037 (2)	0.0299 (19)	0.0350 (17)	−0.0013 (16)	0.0028 (15)	−0.0056 (14)
C5	0.0317 (19)	0.035 (2)	0.0302 (16)	−0.0052 (17)	0.0000 (14)	0.0018 (15)
C6	0.0272 (18)	0.037 (2)	0.0382 (17)	0.0032 (16)	0.0015 (14)	0.0008 (15)
C7	0.0325 (19)	0.0290 (18)	0.0372 (17)	−0.0011 (15)	0.0006 (14)	0.0003 (14)
C8	0.034 (2)	0.063 (3)	0.059 (2)	−0.017 (2)	0.0014 (18)	−0.013 (2)
S2	0.0350 (5)	0.0349 (5)	0.0861 (7)	−0.0018 (4)	−0.0067 (5)	0.0092 (5)
C9	0.0255 (16)	0.0361 (17)	0.0341 (16)	−0.0004 (14)	0.0063 (13)	0.0050 (13)
C10	0.0256 (17)	0.0305 (19)	0.0322 (15)	−0.0034 (15)	0.0011 (13)	0.0031 (14)
C11	0.0300 (18)	0.0228 (17)	0.0361 (16)	0.0048 (14)	0.0041 (14)	−0.0014 (13)
C12	0.0229 (17)	0.044 (2)	0.0376 (17)	0.0019 (16)	0.0033 (14)	−0.0002 (15)
C13	0.0293 (19)	0.040 (2)	0.0335 (17)	−0.0041 (17)	0.0001 (14)	0.0033 (16)
C14	0.042 (2)	0.035 (2)	0.0369 (17)	−0.0029 (17)	0.0026 (16)	−0.0066 (15)
C15	0.0305 (18)	0.034 (2)	0.0415 (18)	0.0048 (16)	0.0071 (14)	−0.0055 (15)
C16	0.039 (2)	0.061 (3)	0.060 (2)	−0.017 (2)	0.0008 (19)	−0.015 (2)
N2	0.0249 (16)	0.0296 (16)	0.0475 (16)	−0.0021 (12)	0.0017 (13)	−0.0009 (12)

Geometric parameters (Å, º) top

S1—C1	1.659 (3)	S2—C9	1.664 (3)
N1—C1	1.321 (4)	C9—N2	1.316 (4)
N1—C2	1.423 (4)	C9—C9ⁱⁱ	1.534 (6)
N1—H1	0.86	C10—C15	1.383 (5)
C1—C1ⁱ	1.538 (6)	C10—C11	1.387 (4)
C2—C7	1.383 (5)	C10—N2	1.426 (4)
C2—C3	1.384 (5)	C11—C12	1.378 (4)
C3—C4	1.386 (5)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.385 (5)
C4—C5	1.383 (5)	C12—H12	0.93
C4—H4	0.93	C13—C14	1.381 (5)
C5—C6	1.386 (5)	C13—C16	1.508 (5)
C5—C8	1.508 (5)	C14—C15	1.383 (5)
C6—C7	1.387 (4)	C14—H14	0.93
C6—H6	0.93	C15—H15	0.93
C7—H7	0.93	C16—H16A	0.96
C8—H8A	0.96	C16—H16B	0.96
C8—H8B	0.96	C16—H16C	0.96
C8—H8C	0.96	C16—H16D	0.96
C8—H8D	0.96	C16—H16E	0.96
C8—H8E	0.96	C16—H16F	0.96
C8—H8F	0.96	N2—H2	0.86

C1—N1—C2	130.9 (3)	N2—C9—C9ⁱⁱ	112.9 (3)
C1—N1—H1	114.6	N2—C9—S2	126.5 (2)
C2—N1—H1	114.6	C9ⁱⁱ—C9—S2	120.6 (3)
N1—C1—C1ⁱ	112.7 (3)	C15—C10—C11	119.9 (3)
N1—C1—S1	126.6 (2)	C15—C10—N2	123.1 (3)
C1ⁱ—C1—S1	120.7 (3)	C11—C10—N2	116.9 (3)
C7—C2—C3	119.8 (3)	C12—C11—C10	120.0 (3)
C7—C2—N1	117.0 (3)	C12—C11—H11	120
C3—C2—N1	123.1 (3)	C10—C11—H11	120
C2—C3—C4	119.6 (3)	C11—C12—C13	121.1 (3)
C2—C3—H3	120.2	C11—C12—H12	119.4
C4—C3—H3	120.2	C13—C12—H12	119.4
C5—C4—C3	121.4 (3)	C14—C13—C12	117.9 (3)
C5—C4—H4	119.3	C14—C13—C16	120.8 (3)
C3—C4—H4	119.3	C12—C13—C16	121.3 (3)
C4—C5—C6	118.2 (3)	C13—C14—C15	122.1 (3)
C4—C5—C8	120.8 (3)	C13—C14—H14	118.9
C6—C5—C8	121.0 (3)	C15—C14—H14	118.9
C5—C6—C7	121.1 (3)	C14—C15—C10	119.0 (3)
C5—C6—H6	119.5	C14—C15—H15	120.5
C7—C6—H6	119.5	C10—C15—H15	120.5
C2—C7—C6	119.9 (3)	C13—C16—H16A	109.5
C2—C7—H7	120.1	C13—C16—H16B	109.5
C6—C7—H7	120.1	H16A—C16—H16B	109.5
C5—C8—H8A	109.5	C13—C16—H16C	109.5
C5—C8—H8B	109.5	H16A—C16—H16C	109.5
H8A—C8—H8B	109.5	H16B—C16—H16C	109.5
C5—C8—H8C	109.5	C13—C16—H16D	109.5
H8A—C8—H8C	109.5	H16A—C16—H16D	141.1
H8B—C8—H8C	109.5	H16B—C16—H16D	56.3
C5—C8—H8D	109.5	H16C—C16—H16D	56.3
H8A—C8—H8D	141.1	C13—C16—H16E	109.5
H8B—C8—H8D	56.3	H16A—C16—H16E	56.3
H8C—C8—H8D	56.3	H16B—C16—H16E	141.1
C5—C8—H8E	109.5	H16C—C16—H16E	56.3
H8A—C8—H8E	56.3	H16D—C16—H16E	109.5
H8B—C8—H8E	141.1	C13—C16—H16F	109.5
H8C—C8—H8E	56.3	H16A—C16—H16F	56.3
H8D—C8—H8E	109.5	H16B—C16—H16F	56.3
C5—C8—H8F	109.5	H16C—C16—H16F	141.1
H8A—C8—H8F	56.3	H16D—C16—H16F	109.5
H8B—C8—H8F	56.3	H16E—C16—H16F	109.5
H8C—C8—H8F	141.1	C9—N2—C10	130.8 (3)
H8D—C8—H8F	109.5	C9—N2—H2	114.6
H8E—C8—H8F	109.5	C10—N2—H2	114.6

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+3/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.86	2.35	2.904 (3)	122
N2—H2···S2ⁱⁱ	0.86	2.35	2.901 (3)	122
C7—H7···Cg1ⁱⁱⁱ	0.93	2.90	3.587 (3)	132
C11—H11···Cg1^iv	0.93	2.77	3.524 (3)	139
C14—H14···Cg2^v	0.93	2.88	3.654 (3)	142

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+3/2, −y+1/2, −z+1; (iii) x, −y+2, z+1/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) x, −y, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.86	2.35	2.904 (3)	122
N2—H2···S2ⁱⁱ	0.86	2.35	2.901 (3)	122
C7—H7···Cg1ⁱⁱⁱ	0.93	2.90	3.587 (3)	132
C11—H11···Cg1^iv	0.93	2.77	3.524 (3)	139
C14—H14···Cg2^v	0.93	2.88	3.654 (3)	142

Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+3/2, −y+1/2, −z+1; (iii) x, −y+2, z+1/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) x, −y, z−1/2.

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