1,5-Bis(4-iso-propyl-benzyl-idene)thio-carbonohydrazide.

The title compound, C21H26N4S, was synthesized by the condensation reaction of 4-iso-propyl-benzaldehyde with thio-carbohydrazide in ethanol. The planes of the two benzene rings in the mol-ecule are inclined at 22.6 (1)°. In the crystal, pairs of inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into inversion dimers.

Related literature

For applications of thio­carbonohydrazide derivatives, see: Bacchi et al. (2005 ▶); Han et al. (2007 ▶). For the crystal structures of related compounds, see: Gao (2013 ▶); Yu et al. (2013 ▶).

Experimental

Crystal data

C21H26N4S

M = 366.52

Monoclinic,

a = 18.082 (6) Å

b = 11.129 (4) Å

c = 10.617 (3) Å

β = 95.330 (6)°

V = 2127.2 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 296 K

0.21 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEX diffrac­tom­eter with a CCD area detector

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.967, T max = 0.976

10028 measured reflections

3659 independent reflections

1635 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.236

S = 1.08

3659 reflections

239 parameters

410 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813027293/cv5428sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027293/cv5428Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027293/cv5428Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H26N4S	F(000) = 784
Mr = 366.52	Dx = 1.144 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1030 reflections
a = 18.082 (6) Å	θ = 2.7–20.2°
b = 11.129 (4) Å	µ = 0.16 mm−1
c = 10.617 (3) Å	T = 296 K
β = 95.330 (6)°	Block, yellow
V = 2127.2 (12) Å3	0.21 × 0.18 × 0.15 mm
Z = 4

Bruker SMART APEX with a CCD area detector diffractometer	3659 independent reflections
Radiation source: fine-focus sealed tube	1635 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
phi and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −17→21
Tmin = 0.967, Tmax = 0.976	k = −8→13
10028 measured reflections	l = −12→11

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.236	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.1P)2 + 0.1124P] where P = (Fo2 + 2Fc2)/3
3659 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.38 e Å−3
410 restraints	Δρmin = −0.47 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 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.

	x	y	z	Uiso*/Ueq
N1	0.1303 (2)	0.8272 (4)	0.2266 (4)	0.0648 (11)
H1	0.1163	0.8211	0.3016	0.078*
N2	0.1942 (2)	0.7702 (4)	0.1996 (4)	0.0649 (11)
N3	0.0291 (2)	0.9425 (4)	0.1818 (3)	0.0680 (11)
H3	0.0049	0.9959	0.1361	0.082*
N4	0.0053 (2)	0.9097 (3)	0.2969 (3)	0.0621 (10)
S1	0.11024 (8)	0.91415 (15)	−0.00810 (13)	0.0919 (6)
C1	0.0896 (3)	0.8915 (5)	0.1412 (4)	0.0630 (12)
C2	0.2323 (3)	0.7216 (4)	0.2937 (5)	0.0690 (12)
H2	0.2172	0.7302	0.3746	0.083*
C3	0.2989 (3)	0.6530 (5)	0.2757 (5)	0.0693 (12)
C4	0.3340 (3)	0.5859 (5)	0.3754 (6)	0.0888 (15)
H4	0.3173	0.5904	0.4555	0.107*
C5	0.3926 (3)	0.5138 (6)	0.3552 (7)	0.1026 (16)
H5	0.4145	0.4697	0.4231	0.123*
C6	0.4212 (3)	0.5025 (6)	0.2414 (7)	0.1014 (16)
C7	0.3874 (3)	0.5705 (6)	0.1433 (7)	0.1014 (15)
H7	0.4053	0.5660	0.0641	0.122*
C8	0.3284 (3)	0.6442 (5)	0.1592 (6)	0.0869 (14)
H8	0.3075	0.6893	0.0912	0.104*
C9	0.4818 (4)	0.4181 (7)	0.2203 (8)	0.1266 (19)
H9	0.4762	0.3718	0.2974	0.152*
C10	0.4599 (4)	0.3124 (7)	0.1311 (9)	0.156 (3)
H10A	0.4395	0.3429	0.0507	0.234*
H10B	0.4235	0.2636	0.1673	0.234*
H10C	0.5031	0.2648	0.1197	0.234*
C11	0.5593 (4)	0.4607 (8)	0.2642 (10)	0.176 (3)
H11A	0.5871	0.4714	0.1923	0.265*
H11B	0.5835	0.4020	0.3200	0.265*
H11C	0.5565	0.5357	0.3081	0.265*
C12	−0.0521 (3)	0.9657 (5)	0.3280 (4)	0.0636 (12)
H12	−0.0709	1.0296	0.2783	0.076*
C13	−0.0890 (2)	0.9318 (4)	0.4397 (4)	0.0607 (11)
C14	−0.0643 (3)	0.8389 (5)	0.5184 (5)	0.0752 (13)
H14	−0.0213	0.7975	0.5034	0.090*
C15	−0.1028 (3)	0.8071 (5)	0.6185 (5)	0.0846 (14)
H15	−0.0838	0.7461	0.6720	0.102*
C16	−0.1689 (3)	0.8621 (5)	0.6435 (5)	0.0716 (12)
C17	−0.1916 (3)	0.9581 (5)	0.5653 (5)	0.0731 (12)
H17	−0.2343	1.0001	0.5804	0.088*
C18	−0.1526 (3)	0.9926 (5)	0.4665 (4)	0.0699 (12)
H18	−0.1691	1.0577	0.4166	0.084*
C19	−0.2112 (3)	0.8149 (5)	0.7515 (6)	0.0901 (16)
H19	−0.1737	0.7960	0.8213	0.108*
C20	−0.2469 (4)	0.6994 (6)	0.7122 (7)	0.125 (2)
H20A	−0.2697	0.6653	0.7820	0.188*
H20B	−0.2100	0.6450	0.6860	0.188*
H20C	−0.2840	0.7131	0.6430	0.188*
C21	−0.2629 (4)	0.9014 (7)	0.8022 (6)	0.119 (2)
H21A	−0.3039	0.9159	0.7400	0.178*
H21B	−0.2373	0.9755	0.8224	0.178*
H21C	−0.2810	0.8689	0.8773	0.178*

	U11	U22	U33	U12	U13	U23
N1	0.058 (2)	0.076 (3)	0.063 (2)	0.002 (2)	0.0203 (19)	−0.008 (2)
N2	0.056 (2)	0.071 (3)	0.070 (3)	−0.001 (2)	0.017 (2)	−0.010 (2)
N3	0.064 (2)	0.085 (3)	0.058 (2)	0.010 (2)	0.0209 (19)	−0.006 (2)
N4	0.058 (2)	0.074 (3)	0.056 (2)	−0.002 (2)	0.0155 (18)	−0.0111 (19)
S1	0.0794 (10)	0.1351 (15)	0.0648 (8)	0.0252 (9)	0.0251 (7)	0.0002 (8)
C1	0.058 (3)	0.073 (3)	0.060 (3)	0.002 (2)	0.016 (2)	−0.009 (2)
C2	0.060 (2)	0.068 (3)	0.081 (3)	−0.006 (2)	0.019 (2)	−0.007 (2)
C3	0.056 (2)	0.067 (3)	0.087 (3)	−0.005 (2)	0.016 (2)	−0.009 (2)
C4	0.073 (3)	0.092 (3)	0.103 (3)	0.002 (3)	0.013 (3)	−0.005 (3)
C5	0.083 (3)	0.098 (3)	0.125 (3)	0.010 (3)	0.001 (3)	−0.008 (3)
C6	0.071 (3)	0.100 (3)	0.133 (4)	0.013 (3)	0.012 (3)	−0.021 (3)
C7	0.074 (3)	0.109 (3)	0.124 (3)	0.007 (3)	0.024 (3)	−0.019 (3)
C8	0.063 (3)	0.094 (3)	0.106 (3)	0.004 (2)	0.022 (2)	−0.008 (3)
C9	0.094 (4)	0.124 (4)	0.161 (4)	0.018 (3)	0.010 (3)	−0.023 (4)
C10	0.127 (5)	0.125 (5)	0.218 (7)	0.023 (5)	0.018 (5)	−0.034 (5)
C11	0.118 (5)	0.178 (7)	0.231 (8)	0.042 (5)	0.001 (5)	−0.047 (6)
C12	0.061 (2)	0.072 (3)	0.060 (2)	0.009 (2)	0.015 (2)	0.000 (2)
C13	0.060 (2)	0.064 (3)	0.059 (2)	0.009 (2)	0.011 (2)	−0.001 (2)
C14	0.068 (3)	0.076 (3)	0.084 (3)	0.014 (2)	0.019 (2)	0.011 (2)
C15	0.083 (3)	0.081 (3)	0.092 (3)	0.010 (2)	0.014 (2)	0.022 (2)
C16	0.070 (3)	0.071 (3)	0.075 (3)	0.002 (2)	0.018 (2)	0.005 (2)
C17	0.067 (2)	0.080 (3)	0.075 (3)	0.014 (2)	0.019 (2)	0.004 (2)
C18	0.072 (3)	0.074 (3)	0.066 (2)	0.019 (2)	0.016 (2)	0.009 (2)
C19	0.086 (3)	0.086 (4)	0.101 (3)	−0.005 (3)	0.022 (3)	0.016 (3)
C20	0.126 (5)	0.117 (5)	0.136 (5)	−0.017 (4)	0.033 (4)	0.013 (4)
C21	0.119 (5)	0.128 (5)	0.117 (5)	−0.020 (4)	0.051 (4)	−0.003 (4)

N1—C1	1.324 (6)	C10—H10C	0.9600
N1—N2	1.370 (5)	C11—H11A	0.9600
N1—H1	0.8600	C11—H11B	0.9600
N2—C2	1.279 (6)	C11—H11C	0.9600
N3—C1	1.339 (5)	C12—C13	1.463 (6)
N3—N4	1.381 (5)	C12—H12	0.9300
N3—H3	0.8600	C13—C14	1.376 (6)
N4—C12	1.280 (5)	C13—C18	1.387 (6)
S1—C1	1.681 (5)	C14—C15	1.369 (7)
C2—C3	1.453 (6)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.390 (7)
C3—C8	1.394 (7)	C15—H15	0.9300
C3—C4	1.399 (7)	C16—C17	1.392 (7)
C4—C5	1.362 (8)	C16—C19	1.530 (7)
C4—H4	0.9300	C17—C18	1.371 (6)
C5—C6	1.363 (8)	C17—H17	0.9300
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.383 (9)	C19—C21	1.477 (8)
C6—C9	1.477 (9)	C19—C20	1.480 (8)
C7—C8	1.369 (7)	C19—H19	0.9800
C7—H7	0.9300	C20—H20A	0.9600
C8—H8	0.9300	C20—H20B	0.9600
C9—C11	1.511 (8)	C20—H20C	0.9600
C9—C10	1.538 (8)	C21—H21A	0.9600
C9—H9	0.9800	C21—H21B	0.9600
C10—H10A	0.9600	C21—H21C	0.9600
C10—H10B	0.9600
C1—N1—N2	122.2 (4)	C9—C11—H11B	109.5
C1—N1—H1	118.9	H11A—C11—H11B	109.5
N2—N1—H1	118.9	C9—C11—H11C	109.5
C2—N2—N1	115.9 (4)	H11A—C11—H11C	109.5
C1—N3—N4	120.3 (4)	H11B—C11—H11C	109.5
C1—N3—H3	119.9	N4—C12—C13	121.7 (4)
N4—N3—H3	119.9	N4—C12—H12	119.2
C12—N4—N3	115.3 (4)	C13—C12—H12	119.2
N1—C1—N3	115.3 (4)	C14—C13—C18	118.0 (4)
N1—C1—S1	124.7 (3)	C14—C13—C12	122.7 (4)
N3—C1—S1	120.0 (4)	C18—C13—C12	119.3 (4)
N2—C2—C3	120.8 (5)	C15—C14—C13	120.4 (5)
N2—C2—H2	119.6	C15—C14—H14	119.8
C3—C2—H2	119.6	C13—C14—H14	119.8
C8—C3—C4	116.7 (5)	C14—C15—C16	122.8 (5)
C8—C3—C2	122.9 (5)	C14—C15—H15	118.6
C4—C3—C2	120.3 (5)	C16—C15—H15	118.6
C5—C4—C3	120.0 (6)	C15—C16—C17	115.8 (4)
C5—C4—H4	120.0	C15—C16—C19	119.4 (5)
C3—C4—H4	120.0	C17—C16—C19	124.8 (5)
C4—C5—C6	123.9 (7)	C18—C17—C16	121.8 (5)
C4—C5—H5	118.0	C18—C17—H17	119.1
C6—C5—H5	118.0	C16—C17—H17	119.1
C5—C6—C7	116.1 (6)	C17—C18—C13	121.0 (5)
C5—C6—C9	122.7 (7)	C17—C18—H18	119.5
C7—C6—C9	121.1 (7)	C13—C18—H18	119.5
C8—C7—C6	122.0 (6)	C21—C19—C20	113.3 (5)
C8—C7—H7	119.0	C21—C19—C16	115.3 (5)
C6—C7—H7	119.0	C20—C19—C16	108.8 (5)
C7—C8—C3	121.2 (6)	C21—C19—H19	106.3
C7—C8—H8	119.4	C20—C19—H19	106.3
C3—C8—H8	119.4	C16—C19—H19	106.3
C6—C9—C11	115.7 (6)	C19—C20—H20A	109.5
C6—C9—C10	115.3 (6)	C19—C20—H20B	109.5
C11—C9—C10	127.4 (7)	H20A—C20—H20B	109.5
C6—C9—H9	94.1	C19—C20—H20C	109.5
C11—C9—H9	94.1	H20A—C20—H20C	109.5
C10—C9—H9	94.1	H20B—C20—H20C	109.5
C9—C10—H10A	109.5	C19—C21—H21A	109.5
C9—C10—H10B	109.5	C19—C21—H21B	109.5
H10A—C10—H10B	109.5	H21A—C21—H21B	109.5
C9—C10—H10C	109.5	C19—C21—H21C	109.5
H10A—C10—H10C	109.5	H21A—C21—H21C	109.5
H10B—C10—H10C	109.5	H21B—C21—H21C	109.5
C9—C11—H11A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1i	0.86	2.58	3.381 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯S1i	0.86	2.58	3.381 (4)	155

Symmetry code: (i) .