Benzyl N′-benzhydrylidene­hydrazine­carbodithio­ate

Zhang, B.-X.

doi:10.1107/S1600536808039408

organic compounds

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Volume 64| Part 12| December 2008| Page o2477

doi:10.1107/S1600536808039408

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Benzyl N′-benzhydrylidenehydrazinecarbodithioate

Bing-Xiang Zhang ^a ^*

^aDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: bezhbx@163.com

(Received 4 November 2008; accepted 24 November 2008; online 29 November 2008)

In the title molecule, C₂₁H₁₈N₂S₂, the C=N—N angle of 117.6 (2)° is significantly smaller than the ideal value of 120° expected for sp²-hybridized N atoms. This is probably a consequence of repulsion between the nitrogen lone pairs and the adjacent N atom, as suggested in Zheng, Qiu, Lin & Liu [Acta Cryst. (2006), E62, o1913–o1914]. The two neighbouring benzene rings form a dihedral angle of 75.95 (3)° with each other, while subtending dihedral angles of 84.18 (3) and 8.44 (2)° with the third ring in the structure.

Related literature

For related literature on ligands derived from S-benzyldithiocarbazate (SBDTC), see: Ali et al. (2002 , 2008 ); Crouse et al. (2004 ); Tarafder et al. (2001 , 2008 ); Zheng et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₈N₂S₂
M_r = 362.49
Monoclinic, P 2₁ /c
a = 20.2903 (14) Å
b = 9.0951 (6) Å
c = 10.5818 (7) Å
β = 103.9240 (10)°
V = 1895.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 295 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.967, T_max = 0.983
9776 measured reflections
3363 independent reflections
2191 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.116
S = 1.05
3363 reflections
214 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039408/bg2222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039408/bg2222Isup2.hkl

checkCIF report

Comment top

In recent years, the interesting coordination chemistry and increasingly relevant biomedical properties of ligands derived from S-benzyldithiocarbazate(SBDTC) have received much attention (Ali et al., 2002, 2008; Crouse et al., 2004; Tarafder et al., 2001, 2008). In order to search for new ligands derived from SBDTC, the title compound C₂₁H₁₈N₂S₂ (I) was synthesized and its crystal structure determined. Fig 1 shows a molecular diagram of (I), where bond lengths and angles are basically in normal ranges (Allen et al., 1987). The C=N bond length of 1.293 (3) Å(C9=N2) shows double-bond character. The C=N—N angle of 117.6 (2) ° is significantly smaller than the ideal value of 120 ° expected for sp²-hybridized N atoms. This is probably a consequence of repulsion between the nitrogen lone pairs and the adjacent N atom (Zheng et al., 2006). The C10—C15, C16—C21 benzene rings are oriented at 84.18 (3) °, 8.44 (2) ° with respect to the C1—C6 one. The dihedral angle formed by the C10—C15 and C16—C21 rings is 75.95 (3) °.

Related literature top

For related literature on ligands derived from S-benzyldithiocarbazate (SBDTC), see: Ali et al. (2002, 2008); Crouse et al. (2004); Tarafder et al. (2001, 2008); Zheng et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by the reaction of Hydrazinecarbodithioic acid benzyl ester(1 mmol, 198.3 mg) with Diphenyl-methanone(1 mmol, 182.2 mg) in ethanol(15 ml) under reflux conditions (338 K) for 5 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After six days yellow crystals suitable for X-ray diffraction study were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.

Benzyl N'-benzhydrylidenehydrazinecarbodithioate top

Crystal data top

C₂₁H₁₈N₂S₂	F(000) = 760
M_r = 362.49	D_x = 1.270 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1615 reflections
a = 20.2903 (14) Å	θ = 3.0–22.7°
b = 9.0951 (6) Å	µ = 0.29 mm⁻¹
c = 10.5818 (7) Å	T = 295 K
β = 103.924 (1)°	Block, yellow
V = 1895.4 (2) Å³	0.12 × 0.10 × 0.06 mm
Z = 4

Data collection top

Bruker APEX2 CCD area-detector diffractometer	3363 independent reflections
Radiation source: fine-focus sealed tube	2191 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −24→24
T_min = 0.967, T_max = 0.983	k = −10→10
9776 measured reflections	l = −11→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0462P)² + 0.2919P] where P = (F_o² + 2F_c²)/3
3363 reflections	(Δ/σ)_max = 0.001
214 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₁₈N₂S₂	V = 1895.4 (2) Å³
M_r = 362.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.2903 (14) Å	µ = 0.29 mm⁻¹
b = 9.0951 (6) Å	T = 295 K
c = 10.5818 (7) Å	0.12 × 0.10 × 0.06 mm
β = 103.924 (1)°

Data collection top

Bruker APEX2 CCD area-detector diffractometer	3363 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2191 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.983	R_int = 0.039
9776 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
3363 reflections	Δρ_min = −0.23 e Å⁻³
214 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 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	0.29194 (4)	0.73862 (8)	0.23650 (8)	0.0593 (2)
S2	0.15831 (4)	0.59677 (8)	0.10325 (8)	0.0636 (3)
N1	0.17341 (11)	0.8548 (2)	0.2139 (2)	0.0539 (6)
H1	0.1299	0.8630	0.1909	0.065*
N2	0.21181 (11)	0.9673 (2)	0.2809 (2)	0.0508 (6)
C1	0.39011 (8)	0.5783 (2)	0.1752 (2)	0.0578 (8)
C2	0.41212 (13)	0.6495 (2)	0.0766 (2)	0.0836 (10)
H2	0.3807	0.6909	0.0070	0.100*
C3	0.48112 (15)	0.6589 (3)	0.0820 (3)	0.1024 (13)
H3	0.4958	0.7065	0.0160	0.123*
C4	0.52811 (9)	0.5971 (3)	0.1861 (3)	0.1042 (14)
H4	0.5743	0.6034	0.1897	0.125*
C5	0.50611 (11)	0.5259 (3)	0.2847 (3)	0.1084 (14)
H5	0.5376	0.4845	0.3543	0.130*
C6	0.43711 (12)	0.5165 (3)	0.2793 (2)	0.0868 (11)
H6	0.4224	0.4689	0.3452	0.104*
C7	0.31560 (14)	0.5689 (3)	0.1698 (4)	0.0709 (9)
H7A	0.3065	0.4857	0.2204	0.085*
H7B	0.2898	0.5566	0.0805	0.085*
C8	0.20349 (13)	0.7318 (3)	0.1840 (2)	0.0475 (7)
C9	0.18138 (13)	1.0901 (3)	0.2909 (2)	0.0450 (6)
C10	0.22361 (13)	1.2075 (3)	0.3651 (2)	0.0449 (6)
C11	0.29263 (14)	1.1870 (3)	0.4165 (3)	0.0603 (8)
H11	0.3129	1.0997	0.4000	0.072*
C12	0.33158 (15)	1.2931 (3)	0.4912 (3)	0.0714 (9)
H12	0.3777	1.2770	0.5256	0.086*
C13	0.30214 (17)	1.4240 (3)	0.5153 (3)	0.0718 (9)
H13	0.3284	1.4959	0.5664	0.086*
C14	0.23479 (16)	1.4474 (3)	0.4641 (3)	0.0664 (8)
H14	0.2153	1.5362	0.4792	0.080*
C15	0.19518 (15)	1.3404 (3)	0.3898 (3)	0.0554 (7)
H15	0.1491	1.3574	0.3559	0.067*
C16	0.10755 (13)	1.1135 (3)	0.2328 (2)	0.0437 (6)
C17	0.05888 (14)	1.0439 (3)	0.2829 (3)	0.0564 (7)
H17	0.0723	0.9829	0.3550	0.068*
C18	−0.00925 (15)	1.0638 (3)	0.2275 (3)	0.0653 (8)
H18	−0.0414	1.0176	0.2634	0.078*
C19	−0.02962 (16)	1.1503 (3)	0.1210 (3)	0.0664 (9)
H19	−0.0757	1.1632	0.0839	0.080*
C20	0.01760 (16)	1.2191 (3)	0.0678 (3)	0.0670 (8)
H20	0.0035	1.2776	−0.0058	0.080*
C21	0.08623 (15)	1.2016 (3)	0.1237 (3)	0.0569 (7)
H21	0.1181	1.2491	0.0880	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0445 (4)	0.0491 (4)	0.0788 (6)	0.0040 (3)	0.0042 (4)	−0.0127 (4)
S2	0.0521 (5)	0.0564 (5)	0.0746 (6)	−0.0006 (4)	0.0000 (4)	−0.0137 (4)
N1	0.0414 (13)	0.0488 (13)	0.0692 (16)	0.0060 (11)	0.0091 (12)	−0.0080 (12)
N2	0.0458 (14)	0.0466 (13)	0.0590 (15)	0.0028 (11)	0.0109 (11)	−0.0066 (12)
C1	0.0502 (18)	0.0447 (16)	0.075 (2)	0.0061 (14)	0.0092 (16)	−0.0101 (16)
C2	0.079 (3)	0.085 (2)	0.083 (3)	0.004 (2)	0.012 (2)	0.005 (2)
C3	0.092 (3)	0.112 (3)	0.113 (3)	−0.017 (3)	0.043 (3)	−0.008 (3)
C4	0.056 (2)	0.103 (3)	0.157 (4)	−0.003 (2)	0.032 (3)	−0.015 (3)
C5	0.055 (2)	0.116 (3)	0.142 (4)	0.008 (2)	0.000 (2)	0.022 (3)
C6	0.057 (2)	0.096 (3)	0.105 (3)	0.004 (2)	0.013 (2)	0.022 (2)
C7	0.0489 (18)	0.0562 (18)	0.106 (3)	0.0071 (15)	0.0148 (17)	−0.0217 (19)
C8	0.0460 (16)	0.0449 (15)	0.0490 (16)	0.0064 (13)	0.0061 (13)	0.0026 (13)
C9	0.0434 (15)	0.0456 (15)	0.0471 (16)	0.0044 (13)	0.0131 (13)	0.0009 (13)
C10	0.0455 (16)	0.0438 (14)	0.0474 (16)	−0.0001 (13)	0.0149 (13)	0.0013 (13)
C11	0.0478 (18)	0.0486 (16)	0.085 (2)	−0.0010 (14)	0.0170 (16)	−0.0034 (17)
C12	0.0443 (18)	0.069 (2)	0.096 (3)	−0.0064 (16)	0.0091 (17)	−0.006 (2)
C13	0.068 (2)	0.066 (2)	0.081 (2)	−0.0139 (18)	0.0166 (19)	−0.0177 (18)
C14	0.065 (2)	0.0560 (18)	0.078 (2)	0.0044 (16)	0.0167 (18)	−0.0150 (17)
C15	0.0504 (17)	0.0555 (17)	0.0610 (19)	0.0064 (14)	0.0148 (15)	−0.0089 (15)
C16	0.0435 (16)	0.0386 (14)	0.0478 (16)	0.0057 (12)	0.0087 (13)	−0.0025 (13)
C17	0.0494 (18)	0.0600 (18)	0.0606 (18)	0.0050 (14)	0.0145 (15)	0.0111 (15)
C18	0.0477 (19)	0.075 (2)	0.074 (2)	−0.0001 (16)	0.0154 (16)	0.0044 (19)
C19	0.0477 (19)	0.065 (2)	0.078 (2)	0.0080 (16)	−0.0017 (17)	−0.0048 (18)
C20	0.067 (2)	0.066 (2)	0.060 (2)	0.0142 (17)	−0.0012 (17)	0.0090 (17)
C21	0.0591 (19)	0.0528 (16)	0.0591 (18)	0.0061 (15)	0.0148 (15)	0.0070 (15)

Geometric parameters (Å, º) top

S1—C8	1.747 (3)	C10—C11	1.388 (4)
S1—C7	1.810 (3)	C10—C15	1.391 (3)
S2—C8	1.643 (3)	C11—C12	1.371 (4)
N1—C8	1.348 (3)	C11—H11	0.9300
N1—N2	1.375 (3)	C12—C13	1.383 (4)
N1—H1	0.8600	C12—H12	0.9300
N2—C9	1.293 (3)	C13—C14	1.360 (4)
C1—C2	1.3900	C13—H13	0.9300
C1—C6	1.3900	C14—C15	1.381 (4)
C1—C7	1.501 (3)	C14—H14	0.9300
C2—C3	1.3900	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.381 (4)
C3—C4	1.3900	C16—C21	1.386 (3)
C3—H3	0.9300	C17—C18	1.377 (4)
C4—C5	1.3900	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.355 (4)
C5—C6	1.3900	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.373 (4)
C6—H6	0.9300	C19—H19	0.9300
C7—H7A	0.9700	C20—C21	1.385 (4)
C7—H7B	0.9700	C20—H20	0.9300
C9—C10	1.472 (3)	C21—H21	0.9300
C9—C16	1.491 (3)

C8—S1—C7	101.19 (13)	C11—C10—C9	121.0 (2)
C8—N1—N2	120.4 (2)	C15—C10—C9	121.1 (2)
C8—N1—H1	119.8	C12—C11—C10	121.3 (3)
N2—N1—H1	119.8	C12—C11—H11	119.4
C9—N2—N1	117.6 (2)	C10—C11—H11	119.4
C2—C1—C6	120.0	C11—C12—C13	119.8 (3)
C2—C1—C7	120.0 (2)	C11—C12—H12	120.1
C6—C1—C7	120.0 (2)	C13—C12—H12	120.1
C3—C2—C1	120.0	C14—C13—C12	119.9 (3)
C3—C2—H2	120.0	C14—C13—H13	120.0
C1—C2—H2	120.0	C12—C13—H13	120.0
C2—C3—C4	120.0	C13—C14—C15	120.5 (3)
C2—C3—H3	120.0	C13—C14—H14	119.7
C4—C3—H3	120.0	C15—C14—H14	119.7
C5—C4—C3	120.0	C14—C15—C10	120.6 (3)
C5—C4—H4	120.0	C14—C15—H15	119.7
C3—C4—H4	120.0	C10—C15—H15	119.7
C4—C5—C6	120.0	C17—C16—C21	118.4 (3)
C4—C5—H5	120.0	C17—C16—C9	121.1 (2)
C6—C5—H5	120.0	C21—C16—C9	120.5 (2)
C5—C6—C1	120.0	C18—C17—C16	120.9 (3)
C5—C6—H6	120.0	C18—C17—H17	119.5
C1—C6—H6	120.0	C16—C17—H17	119.5
C1—C7—S1	107.18 (18)	C19—C18—C17	120.2 (3)
C1—C7—H7A	110.3	C19—C18—H18	119.9
S1—C7—H7A	110.3	C17—C18—H18	119.9
C1—C7—H7B	110.3	C18—C19—C20	120.1 (3)
S1—C7—H7B	110.3	C18—C19—H19	119.9
H7A—C7—H7B	108.5	C20—C19—H19	119.9
N1—C8—S2	121.0 (2)	C19—C20—C21	120.1 (3)
N1—C8—S1	112.58 (19)	C19—C20—H20	119.9
S2—C8—S1	126.42 (15)	C21—C20—H20	119.9
N2—C9—C10	116.3 (2)	C20—C21—C16	120.2 (3)
N2—C9—C16	122.8 (2)	C20—C21—H21	119.9
C10—C9—C16	120.9 (2)	C16—C21—H21	119.9
C11—C10—C15	117.9 (3)

C8—N1—N2—C9	170.5 (2)	C16—C9—C10—C15	3.9 (4)
C6—C1—C2—C3	0.0	C15—C10—C11—C12	1.1 (4)
C7—C1—C2—C3	179.7 (2)	C9—C10—C11—C12	−176.6 (3)
C1—C2—C3—C4	0.0	C10—C11—C12—C13	−0.7 (5)
C2—C3—C4—C5	0.0	C11—C12—C13—C14	−0.4 (5)
C3—C4—C5—C6	0.0	C12—C13—C14—C15	1.0 (5)
C4—C5—C6—C1	0.0	C13—C14—C15—C10	−0.6 (5)
C2—C1—C6—C5	0.0	C11—C10—C15—C14	−0.5 (4)
C7—C1—C6—C5	−179.7 (2)	C9—C10—C15—C14	177.3 (2)
C2—C1—C7—S1	−83.8 (2)	N2—C9—C16—C17	70.2 (3)
C6—C1—C7—S1	95.8 (2)	C10—C9—C16—C17	−109.1 (3)
C8—S1—C7—C1	164.8 (2)	N2—C9—C16—C21	−107.4 (3)
N2—N1—C8—S2	−179.69 (18)	C10—C9—C16—C21	73.4 (3)
N2—N1—C8—S1	−1.2 (3)	C21—C16—C17—C18	−1.2 (4)
C7—S1—C8—N1	−175.2 (2)	C9—C16—C17—C18	−178.8 (3)
C7—S1—C8—S2	3.2 (2)	C16—C17—C18—C19	1.1 (4)
N1—N2—C9—C10	179.0 (2)	C17—C18—C19—C20	−0.1 (5)
N1—N2—C9—C16	−0.3 (4)	C18—C19—C20—C21	−0.7 (4)
N2—C9—C10—C11	2.3 (4)	C19—C20—C21—C16	0.6 (4)
C16—C9—C10—C11	−178.4 (2)	C17—C16—C21—C20	0.3 (4)
N2—C9—C10—C15	−175.4 (2)	C9—C16—C21—C20	178.0 (2)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₂S₂
M_r	362.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	20.2903 (14), 9.0951 (6), 10.5818 (7)
β (°)	103.924 (1)
V (Å³)	1895.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.967, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	9776, 3363, 2191
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.116, 1.05
No. of reflections	3363
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008.

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (No. Y03–1–13).

References

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