1,5-Bis[1-(4-meth-oxy-phen-yl)ethyl-idene]thio-carbonohydrazide.

In the title mol-ecule, C(19)H(22)N(4)O(2)S, the two benzene rings form a dihedral angle of 9.16 (13)°. In the crystal, pairs of weak inter-molecular C-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers, which are further linked through weak C-H⋯O inter-actions into sheets parallel to (012).

Related literature

For related Schiff base derivatives of thio­carbonohydrazide, see: Loncle et al. (2004 ▶); Camp et al. (2010 ▶). For a related structure, see: Affan et al. (2010 ▶).

Experimental

Crystal data

C19H22N4O2S

M = 370.47

Monoclinic,

a = 7.4225 (6) Å

b = 11.4705 (11) Å

c = 21.749 (2) Å

β = 91.781 (1)°

V = 1850.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 298 K

0.41 × 0.39 × 0.35 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.924, T max = 0.935

9108 measured reflections

3256 independent reflections

1829 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.135

S = 1.05

3256 reflections

239 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 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/S1600536811029023/cv5100sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029023/cv5100Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029023/cv5100Isup3.cml

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

C19H22N4O2S	F(000) = 784
Mr = 370.47	Dx = 1.330 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.4225 (6) Å	Cell parameters from 1954 reflections
b = 11.4705 (11) Å	θ = 2.6–21.8°
c = 21.749 (2) Å	µ = 0.20 mm−1
β = 91.781 (1)°	T = 298 K
V = 1850.8 (3) Å3	Block, yellow
Z = 4	0.41 × 0.39 × 0.35 mm

Bruker SMART APEX CCD area-detector diffractometer	3256 independent reflections
Radiation source: fine-focus sealed tube	1829 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.924, Tmax = 0.935	k = −13→13
9108 measured reflections	l = −25→25

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.9707P] where P = (Fo2 + 2Fc2)/3
3256 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.21 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
S1	0.89899 (14)	0.14956 (8)	1.05758 (4)	0.0558 (3)
N1	0.9376 (4)	0.1693 (2)	0.93818 (11)	0.0464 (7)
H1	0.9799	0.0995	0.9382	0.056*
N2	0.9174 (4)	0.2304 (2)	0.88416 (12)	0.0441 (7)
N3	0.8371 (4)	0.3316 (2)	0.98297 (12)	0.0493 (7)
H3	0.8383	0.3611	0.9466	0.059*
N4	0.7809 (4)	0.3991 (2)	1.03058 (12)	0.0462 (7)
O1	0.8713 (4)	0.46947 (19)	0.62470 (10)	0.0617 (7)
O2	0.5350 (4)	0.78761 (19)	1.21510 (11)	0.0650 (7)
C1	0.8904 (4)	0.2201 (3)	0.99129 (14)	0.0416 (8)
C2	0.9728 (4)	0.1862 (3)	0.83430 (14)	0.0404 (8)
C3	1.0640 (6)	0.0700 (3)	0.83080 (16)	0.0620 (11)
H3A	1.1369	0.0577	0.8675	0.093*
H3B	1.1389	0.0682	0.7956	0.093*
H3C	0.9746	0.0097	0.8271	0.093*
C4	0.9453 (4)	0.2574 (3)	0.77845 (14)	0.0397 (8)
C5	0.8960 (5)	0.3744 (3)	0.78197 (15)	0.0489 (9)
H5	0.8768	0.4073	0.8203	0.059*
C6	0.8753 (5)	0.4419 (3)	0.73063 (15)	0.0515 (9)
H6	0.8451	0.5202	0.7345	0.062*
C7	0.8987 (5)	0.3951 (3)	0.67283 (15)	0.0456 (8)
C8	0.9468 (5)	0.2803 (3)	0.66780 (15)	0.0497 (9)
H8	0.9647	0.2478	0.6293	0.060*
C9	0.9687 (5)	0.2128 (3)	0.72022 (15)	0.0488 (9)
H9	1.0002	0.1347	0.7161	0.059*
C10	0.8880 (5)	0.4244 (3)	0.56465 (15)	0.0622 (10)
H10A	1.0064	0.3922	0.5605	0.093*
H10B	0.8695	0.4859	0.5352	0.093*
H10C	0.7995	0.3646	0.5574	0.093*
C11	0.7401 (4)	0.5055 (3)	1.01736 (14)	0.0424 (8)
C12	0.7505 (5)	0.5578 (3)	0.95444 (15)	0.0570 (10)
H12A	0.8587	0.5319	0.9356	0.085*
H12B	0.7517	0.6412	0.9577	0.085*
H12C	0.6476	0.5337	0.9297	0.085*
C13	0.6849 (4)	0.5776 (3)	1.06957 (14)	0.0393 (8)
C14	0.7042 (5)	0.5384 (3)	1.12935 (15)	0.0481 (9)
H14	0.7525	0.4646	1.1364	0.058*
C15	0.6550 (5)	0.6040 (3)	1.17903 (15)	0.0503 (9)
H15	0.6707	0.5749	1.2187	0.060*
C16	0.5819 (5)	0.7137 (3)	1.16945 (16)	0.0486 (9)
C17	0.5580 (5)	0.7541 (3)	1.11045 (16)	0.0566 (10)
H17	0.5070	0.8272	1.1036	0.068*
C18	0.6088 (5)	0.6877 (3)	1.06136 (16)	0.0539 (9)
H18	0.5919	0.7170	1.0217	0.065*
C19	0.5427 (5)	0.7484 (3)	1.27698 (16)	0.0628 (10)
H19A	0.4640	0.6827	1.2812	0.094*
H19B	0.5052	0.8102	1.3035	0.094*
H19C	0.6640	0.7260	1.2881	0.094*

	U11	U22	U33	U12	U13	U23
S1	0.0754 (7)	0.0489 (5)	0.0435 (5)	0.0089 (5)	0.0060 (4)	0.0056 (4)
N1	0.062 (2)	0.0384 (15)	0.0387 (16)	0.0058 (14)	0.0058 (14)	0.0021 (13)
N2	0.0564 (19)	0.0396 (15)	0.0365 (16)	0.0022 (14)	0.0035 (13)	0.0019 (13)
N3	0.069 (2)	0.0404 (16)	0.0390 (16)	0.0090 (15)	0.0065 (14)	0.0010 (12)
N4	0.0554 (19)	0.0411 (16)	0.0421 (16)	0.0063 (14)	0.0013 (13)	−0.0048 (13)
O1	0.090 (2)	0.0475 (14)	0.0473 (15)	−0.0034 (13)	0.0007 (13)	0.0103 (12)
O2	0.091 (2)	0.0421 (14)	0.0629 (17)	0.0096 (13)	0.0140 (14)	−0.0056 (12)
C1	0.043 (2)	0.0383 (18)	0.044 (2)	−0.0008 (16)	0.0024 (15)	−0.0028 (15)
C2	0.047 (2)	0.0327 (17)	0.0416 (19)	−0.0051 (15)	0.0052 (16)	−0.0004 (14)
C3	0.094 (3)	0.040 (2)	0.053 (2)	0.008 (2)	0.013 (2)	0.0044 (17)
C4	0.043 (2)	0.0341 (17)	0.0418 (19)	−0.0034 (15)	0.0047 (15)	−0.0017 (15)
C5	0.064 (2)	0.0397 (19)	0.043 (2)	−0.0035 (17)	0.0013 (17)	−0.0059 (16)
C6	0.071 (3)	0.0345 (18)	0.049 (2)	−0.0035 (17)	−0.0032 (18)	−0.0012 (17)
C7	0.051 (2)	0.0391 (19)	0.047 (2)	−0.0077 (16)	0.0031 (17)	0.0078 (16)
C8	0.064 (2)	0.047 (2)	0.039 (2)	0.0009 (18)	0.0059 (17)	−0.0002 (16)
C9	0.066 (3)	0.0331 (17)	0.048 (2)	0.0023 (17)	0.0079 (18)	−0.0005 (16)
C10	0.065 (3)	0.076 (3)	0.046 (2)	0.000 (2)	0.0095 (19)	0.0107 (19)
C11	0.041 (2)	0.0394 (19)	0.046 (2)	0.0008 (16)	−0.0027 (15)	0.0039 (15)
C12	0.070 (3)	0.047 (2)	0.053 (2)	0.0007 (19)	−0.0007 (19)	0.0031 (17)
C13	0.040 (2)	0.0346 (17)	0.043 (2)	−0.0029 (15)	−0.0017 (15)	0.0010 (15)
C14	0.055 (2)	0.0325 (17)	0.056 (2)	0.0041 (16)	0.0022 (18)	0.0044 (16)
C15	0.060 (2)	0.0436 (19)	0.048 (2)	0.0039 (18)	0.0044 (18)	0.0051 (16)
C16	0.049 (2)	0.0371 (19)	0.060 (2)	−0.0026 (17)	0.0070 (18)	−0.0017 (17)
C17	0.071 (3)	0.0379 (19)	0.060 (2)	0.0167 (19)	−0.001 (2)	0.0043 (18)
C18	0.068 (3)	0.044 (2)	0.050 (2)	0.0109 (19)	−0.0017 (18)	0.0056 (16)
C19	0.070 (3)	0.061 (2)	0.057 (2)	−0.006 (2)	0.011 (2)	−0.0051 (19)

S1—C1	1.653 (3)	C8—C9	1.384 (4)
N1—C1	1.350 (4)	C8—H8	0.9300
N1—N2	1.372 (3)	C9—H9	0.9300
N1—H1	0.8600	C10—H10A	0.9600
N2—C2	1.277 (4)	C10—H10B	0.9600
N3—C1	1.349 (4)	C10—H10C	0.9600
N3—N4	1.368 (3)	C11—C13	1.473 (4)
N3—H3	0.8600	C11—C12	1.499 (4)
N4—C11	1.288 (4)	C12—H12A	0.9600
O1—C7	1.361 (4)	C12—H12B	0.9600
O1—C10	1.414 (4)	C12—H12C	0.9600
O2—C16	1.359 (4)	C13—C14	1.379 (4)
O2—C19	1.418 (4)	C13—C18	1.393 (4)
C2—C4	1.472 (4)	C14—C15	1.375 (4)
C2—C3	1.498 (4)	C14—H14	0.9300
C3—H3A	0.9600	C15—C16	1.383 (4)
C3—H3B	0.9600	C15—H15	0.9300
C3—H3C	0.9600	C16—C17	1.371 (4)
C4—C9	1.382 (4)	C17—C18	1.374 (4)
C4—C5	1.394 (4)	C17—H17	0.9300
C5—C6	1.364 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—H19A	0.9600
C6—C7	1.383 (4)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C8	1.370 (4)
C1—N1—N2	119.2 (3)	O1—C10—H10A	109.5
C1—N1—H1	120.4	O1—C10—H10B	109.5
N2—N1—H1	120.4	H10A—C10—H10B	109.5
C2—N2—N1	119.7 (3)	O1—C10—H10C	109.5
C1—N3—N4	122.0 (3)	H10A—C10—H10C	109.5
C1—N3—H3	119.0	H10B—C10—H10C	109.5
N4—N3—H3	119.0	N4—C11—C13	115.4 (3)
C11—N4—N3	116.3 (3)	N4—C11—C12	124.4 (3)
C7—O1—C10	117.8 (3)	C13—C11—C12	120.1 (3)
C16—O2—C19	119.5 (3)	C11—C12—H12A	109.5
N3—C1—N1	112.2 (3)	C11—C12—H12B	109.5
N3—C1—S1	125.8 (2)	H12A—C12—H12B	109.5
N1—C1—S1	122.1 (2)	C11—C12—H12C	109.5
N2—C2—C4	116.1 (3)	H12A—C12—H12C	109.5
N2—C2—C3	123.7 (3)	H12B—C12—H12C	109.5
C4—C2—C3	120.2 (3)	C14—C13—C18	116.5 (3)
C2—C3—H3A	109.5	C14—C13—C11	121.3 (3)
C2—C3—H3B	109.5	C18—C13—C11	122.1 (3)
H3A—C3—H3B	109.5	C15—C14—C13	122.7 (3)
C2—C3—H3C	109.5	C15—C14—H14	118.7
H3A—C3—H3C	109.5	C13—C14—H14	118.7
H3B—C3—H3C	109.5	C14—C15—C16	119.5 (3)
C9—C4—C5	116.6 (3)	C14—C15—H15	120.3
C9—C4—C2	122.2 (3)	C16—C15—H15	120.3
C5—C4—C2	121.2 (3)	O2—C16—C17	116.4 (3)
C6—C5—C4	121.7 (3)	O2—C16—C15	124.4 (3)
C6—C5—H5	119.2	C17—C16—C15	119.2 (3)
C4—C5—H5	119.2	C16—C17—C18	120.6 (3)
C5—C6—C7	120.6 (3)	C16—C17—H17	119.7
C5—C6—H6	119.7	C18—C17—H17	119.7
C7—C6—H6	119.7	C17—C18—C13	121.5 (3)
O1—C7—C8	125.1 (3)	C17—C18—H18	119.2
O1—C7—C6	115.8 (3)	C13—C18—H18	119.2
C8—C7—C6	119.1 (3)	O2—C19—H19A	109.5
C7—C8—C9	119.8 (3)	O2—C19—H19B	109.5
C7—C8—H8	120.1	H19A—C19—H19B	109.5
C9—C8—H8	120.1	O2—C19—H19C	109.5
C4—C9—C8	122.2 (3)	H19A—C19—H19C	109.5
C4—C9—H9	118.9	H19B—C19—H19C	109.5
C8—C9—H9	118.9

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1i	0.93	2.59	3.478 (4)	161.
C3—H3A···S1ii	0.96	2.90	3.503 (3)	122.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1i	0.93	2.59	3.478 (4)	161
C3—H3A⋯S1ii	0.96	2.90	3.503 (3)	122

Symmetry codes: (i) ; (ii) .