1,5-Bis(2-meth-oxy-benzyl-idene)thio-carbonohydrazide methanol monosolvate.

The title compound, C17H18N4O2S·CH3OH, was synthesized by the condensation reaction of o-meth-oxy-benzaldehyde with thio-carbohydrazide in methanol. The two benzene rings are inclined each to other at 31.7 (1)°. Inter-molecular N-H⋯O and bifurcated O-H⋯N(S) hydrogen bonds link two thio-carbonohydrazide and two solvent mol-ecules into a centrosymmetric unit. These units, related by translation along the b axis, are further aggregated into columns through N-H⋯S hydrogen bonds.

Related literature

For biological activities of thio­carbohydrazides, see: Liang (2003 ▶); Bacchi et al. (2005 ▶). For the crystal structures of related compounds, see: Fang et al. (2006 ▶); Feng et al. (2011 ▶); Zhao (2011 ▶).

Experimental

Crystal data

C17H18N4O2S·CH4O

M = 374.46

Triclinic,

a = 7.7223 (15) Å

b = 10.232 (2) Å

c = 12.648 (3) Å

α = 85.938 (3)°

β = 80.796 (3)°

γ = 79.550 (3)°

V = 969.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.25 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.954, T max = 0.966

4769 measured reflections

3324 independent reflections

2766 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.171

S = 1.01

3324 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.20 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/S1600536813016954/cv5415sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016954/cv5415Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016954/cv5415Isup3.cml

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

C17H18N4O2S·CH4O	Z = 2
Mr = 374.46	F(000) = 396
Triclinic, P1	Dx = 1.283 Mg m−3
a = 7.7223 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.232 (2) Å	Cell parameters from 2955 reflections
c = 12.648 (3) Å	θ = 3.0–28.1°
α = 85.938 (3)°	µ = 0.19 mm−1
β = 80.796 (3)°	T = 296 K
γ = 79.550 (3)°	Block, colourless
V = 969.3 (3) Å3	0.25 × 0.21 × 0.18 mm

Bruker SMART APEX CCD area-detector diffractometer	3324 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
phi and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→9
Tmin = 0.954, Tmax = 0.966	k = −9→12
4769 measured reflections	l = −15→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.171	w = 1/[σ2(Fo2) + (0.1P)2 + 0.3851P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.010
3324 reflections	Δρmax = 0.20 e Å−3
240 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (7)

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	0.4120 (3)	0.85311 (18)	0.10378 (15)	0.0503 (5)
H1	0.4497	0.9278	0.0942	0.060*
N2	0.3689 (3)	0.80149 (19)	0.20555 (15)	0.0524 (5)
N3	0.3445 (2)	0.66888 (17)	0.04305 (15)	0.0476 (5)
H3A	0.3322	0.6395	0.1087	0.057*
N4	0.3114 (2)	0.59365 (18)	−0.03557 (15)	0.0480 (5)
O1	0.2688 (4)	1.0468 (2)	0.44226 (17)	0.1014 (9)
O2	0.1142 (3)	0.27193 (17)	0.08315 (18)	0.0739 (6)
S1	0.43309 (9)	0.85466 (6)	−0.10545 (5)	0.0567 (3)
C1	0.3953 (3)	0.7867 (2)	0.01844 (18)	0.0438 (5)
C2	0.3709 (3)	0.8750 (3)	0.28184 (19)	0.0574 (6)
H2	0.3972	0.9601	0.2666	0.069*
C3	0.3324 (4)	0.8276 (3)	0.3932 (2)	0.0644 (7)
C4	0.3466 (6)	0.6932 (3)	0.4199 (3)	0.0963 (11)
H4	0.3800	0.6319	0.3662	0.116*
C5	0.3117 (8)	0.6491 (4)	0.5254 (3)	0.144 (2)
H5	0.3207	0.5585	0.5428	0.173*
C6	0.2634 (8)	0.7397 (5)	0.6049 (3)	0.137 (2)
H6	0.2389	0.7098	0.6760	0.164*
C7	0.2510 (6)	0.8722 (4)	0.5809 (3)	0.1038 (12)
H7	0.2214	0.9324	0.6354	0.125*
C8	0.2826 (4)	0.9174 (3)	0.4751 (2)	0.0720 (7)
C9	0.2107 (7)	1.1424 (4)	0.5220 (3)	0.1161 (15)
H9A	0.0990	1.1274	0.5620	0.174*
H9B	0.1962	1.2301	0.4885	0.174*
H9C	0.2977	1.1346	0.5695	0.174*
C10	0.2413 (3)	0.4934 (2)	0.0006 (2)	0.0487 (5)
H10	0.2192	0.4771	0.0744	0.058*
C11	0.1943 (3)	0.4031 (2)	−0.0700 (2)	0.0543 (6)
C12	0.2091 (4)	0.4269 (3)	−0.1782 (2)	0.0731 (8)
H12	0.2533	0.5019	−0.2087	0.088*
C13	0.1593 (5)	0.3415 (4)	−0.2435 (3)	0.0937 (11)
H13	0.1698	0.3585	−0.3173	0.112*
C14	0.0940 (4)	0.2309 (4)	−0.1973 (3)	0.0958 (12)
H14	0.0581	0.1741	−0.2404	0.115*
C15	0.0809 (4)	0.2032 (3)	−0.0901 (3)	0.0804 (9)
H15	0.0392	0.1268	−0.0607	0.097*
C16	0.1297 (3)	0.2888 (2)	−0.0246 (3)	0.0600 (7)
C17	0.0616 (5)	0.1520 (3)	0.1332 (4)	0.0952 (11)
H17A	−0.0618	0.1534	0.1290	0.143*
H17B	0.0787	0.1458	0.2070	0.143*
H17C	0.1326	0.0766	0.0970	0.143*
O3	0.3985 (3)	0.4521 (2)	0.22744 (16)	0.0803 (6)
H3	0.4610	0.4009	0.1842	0.121*
C18	0.2837 (6)	0.3838 (4)	0.2970 (3)	0.1132 (14)
H18A	0.3517	0.3184	0.3393	0.170*
H18B	0.2173	0.3406	0.2563	0.170*
H18C	0.2031	0.4454	0.3434	0.170*

	U11	U22	U33	U12	U13	U23
N1	0.0627 (11)	0.0401 (10)	0.0515 (11)	−0.0201 (8)	−0.0034 (8)	−0.0085 (8)
N2	0.0588 (11)	0.0468 (10)	0.0529 (11)	−0.0149 (9)	−0.0028 (8)	−0.0086 (9)
N3	0.0554 (10)	0.0389 (9)	0.0514 (10)	−0.0155 (8)	−0.0049 (8)	−0.0098 (8)
N4	0.0496 (10)	0.0398 (9)	0.0569 (11)	−0.0113 (8)	−0.0059 (8)	−0.0129 (8)
O1	0.172 (2)	0.0723 (14)	0.0597 (12)	−0.0446 (15)	0.0175 (13)	−0.0220 (10)
O2	0.0782 (12)	0.0486 (10)	0.1034 (16)	−0.0266 (9)	−0.0268 (11)	0.0098 (10)
S1	0.0740 (4)	0.0492 (4)	0.0532 (4)	−0.0275 (3)	−0.0076 (3)	−0.0062 (3)
C1	0.0403 (10)	0.0361 (10)	0.0555 (12)	−0.0073 (8)	−0.0049 (9)	−0.0098 (9)
C2	0.0680 (14)	0.0541 (13)	0.0526 (13)	−0.0203 (11)	−0.0022 (11)	−0.0106 (11)
C3	0.0760 (16)	0.0634 (16)	0.0527 (14)	−0.0142 (13)	−0.0024 (12)	−0.0053 (12)
C4	0.140 (3)	0.0634 (18)	0.0710 (19)	−0.0009 (19)	0.0064 (19)	−0.0020 (15)
C5	0.235 (6)	0.077 (2)	0.085 (3)	0.015 (3)	0.022 (3)	0.022 (2)
C6	0.212 (5)	0.102 (3)	0.066 (2)	0.021 (3)	0.007 (3)	0.017 (2)
C7	0.146 (3)	0.101 (3)	0.0549 (17)	−0.007 (2)	−0.0002 (19)	−0.0093 (17)
C8	0.0876 (19)	0.0748 (18)	0.0527 (14)	−0.0158 (15)	−0.0034 (13)	−0.0082 (13)
C9	0.188 (4)	0.087 (2)	0.074 (2)	−0.047 (3)	0.019 (2)	−0.0335 (19)
C10	0.0453 (11)	0.0381 (11)	0.0653 (14)	−0.0105 (9)	−0.0103 (10)	−0.0080 (10)
C11	0.0439 (11)	0.0452 (12)	0.0758 (16)	−0.0115 (9)	−0.0040 (10)	−0.0185 (11)
C12	0.0740 (17)	0.0731 (18)	0.0786 (19)	−0.0300 (14)	−0.0008 (14)	−0.0262 (15)
C13	0.098 (2)	0.109 (3)	0.083 (2)	−0.042 (2)	0.0038 (17)	−0.044 (2)
C14	0.085 (2)	0.095 (2)	0.118 (3)	−0.0436 (19)	0.0095 (19)	−0.062 (2)
C15	0.0646 (16)	0.0599 (16)	0.122 (3)	−0.0255 (13)	0.0028 (16)	−0.0369 (17)
C16	0.0412 (11)	0.0383 (12)	0.102 (2)	−0.0056 (9)	−0.0084 (12)	−0.0193 (12)
C17	0.082 (2)	0.0633 (18)	0.148 (3)	−0.0364 (16)	−0.026 (2)	0.026 (2)
O3	0.1011 (15)	0.0707 (13)	0.0658 (12)	−0.0183 (11)	0.0032 (10)	−0.0064 (10)
C18	0.152 (4)	0.103 (3)	0.084 (2)	−0.050 (3)	0.014 (2)	0.000 (2)

N1—C1	1.351 (3)	C7—H7	0.9300
N1—N2	1.370 (3)	C9—H9A	0.9600
N1—H1	0.8600	C9—H9B	0.9600
N2—C2	1.268 (3)	C9—H9C	0.9600
N3—C1	1.335 (3)	C10—C11	1.458 (3)
N3—N4	1.381 (2)	C10—H10	0.9300
N3—H3A	0.8600	C11—C12	1.363 (4)
N4—C10	1.269 (3)	C11—C16	1.404 (3)
O1—C8	1.350 (4)	C12—C13	1.386 (4)
O1—C9	1.419 (4)	C12—H12	0.9300
O2—C16	1.350 (4)	C13—C14	1.377 (5)
O2—C17	1.435 (3)	C13—H13	0.9300
S1—C1	1.672 (2)	C14—C15	1.356 (5)
C2—C3	1.459 (4)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.385 (4)
C3—C4	1.382 (4)	C15—H15	0.9300
C3—C8	1.395 (4)	C17—H17A	0.9600
C4—C5	1.379 (5)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600
C5—C6	1.378 (6)	O3—C18	1.391 (4)
C5—H5	0.9300	O3—H3	0.8200
C6—C7	1.358 (6)	C18—H18A	0.9600
C6—H6	0.9300	C18—H18B	0.9600
C7—C8	1.383 (4)	C18—H18C	0.9600
C1—N1—N2	119.98 (18)	O1—C9—H9C	109.5
C1—N1—H1	120.0	H9A—C9—H9C	109.5
N2—N1—H1	120.0	H9B—C9—H9C	109.5
C2—N2—N1	116.55 (19)	N4—C10—C11	122.0 (2)
C1—N3—N4	120.89 (19)	N4—C10—H10	119.0
C1—N3—H3A	119.6	C11—C10—H10	119.0
N4—N3—H3A	119.6	C12—C11—C16	119.1 (2)
C10—N4—N3	113.93 (19)	C12—C11—C10	122.2 (2)
C8—O1—C9	117.2 (3)	C16—C11—C10	118.7 (2)
C16—O2—C17	118.8 (3)	C11—C12—C13	121.2 (3)
N3—C1—N1	114.5 (2)	C11—C12—H12	119.4
N3—C1—S1	125.35 (17)	C13—C12—H12	119.4
N1—C1—S1	120.10 (16)	C14—C13—C12	118.8 (4)
N2—C2—C3	120.8 (2)	C14—C13—H13	120.6
N2—C2—H2	119.6	C12—C13—H13	120.6
C3—C2—H2	119.6	C15—C14—C13	121.4 (3)
C4—C3—C8	118.6 (3)	C15—C14—H14	119.3
C4—C3—C2	120.9 (3)	C13—C14—H14	119.3
C8—C3—C2	120.5 (2)	C14—C15—C16	119.9 (3)
C5—C4—C3	120.5 (3)	C14—C15—H15	120.0
C5—C4—H4	119.7	C16—C15—H15	120.0
C3—C4—H4	119.7	O2—C16—C15	123.9 (3)
C6—C5—C4	119.7 (4)	O2—C16—C11	116.5 (2)
C6—C5—H5	120.1	C15—C16—C11	119.5 (3)
C4—C5—H5	120.1	O2—C17—H17A	109.5
C7—C6—C5	120.8 (4)	O2—C17—H17B	109.5
C7—C6—H6	119.6	H17A—C17—H17B	109.5
C5—C6—H6	119.6	O2—C17—H17C	109.5
C6—C7—C8	119.8 (3)	H17A—C17—H17C	109.5
C6—C7—H7	120.1	H17B—C17—H17C	109.5
C8—C7—H7	120.1	C18—O3—H3	109.5
O1—C8—C7	124.6 (3)	O3—C18—H18A	109.5
O1—C8—C3	115.0 (2)	O3—C18—H18B	109.5
C7—C8—C3	120.4 (3)	H18A—C18—H18B	109.5
O1—C9—H9A	109.5	O3—C18—H18C	109.5
O1—C9—H9B	109.5	H18A—C18—H18C	109.5
H9A—C9—H9B	109.5	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···S1i	0.82	2.80	3.534 (2)	150
O3—H3···N4i	0.82	2.36	3.028 (3)	139
N3—H3A···O3	0.86	2.38	3.126 (3)	145
N1—H1···S1ii	0.86	2.57	3.4184 (19)	169
N3—H3A···N2	0.86	2.21	2.591 (3)	106

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯S1i	0.82	2.80	3.534 (2)	150
O3—H3⋯N4i	0.82	2.36	3.028 (3)	139
N3—H3A⋯O3	0.86	2.38	3.126 (3)	145
N1—H1⋯S1ii	0.86	2.57	3.4184 (19)	169

Symmetry codes: (i) ; (ii) .