1,5-Bis(4-meth-oxy-benzyl-idene)thio-carbonohydrazide methanol monosolvate.

In the title compound, C(17)H(18)N(4)O(2)S·CH(3)OH, the two benzene rings in the thio-carbonohydrazide mol-ecule form a dihedral angle of 22.42 (18)°. Pairs of N-H⋯S hydrogen bonds link thio-carbonohydrazide mol-ecules into centrosymmetric dimers. Methanol solvent mol-ecules serve as donors (O-H⋯S and O-H⋯N) and acceptors (N-H⋯O and C-H⋯O) of weak inter-molecular hydrogen bonds, which link further these dimers into double ribbons along the b axis.

Related literature

For related Schiff base derivatives of thio­carbohydrazide, see: Loncle et al. (2004 ▶); Camp et al. (2010 ▶); Opstal & Verpoort (2003 ▶). For a related structure, see: Affan et al. (2010 ▶).

Experimental

Crystal data

C17H18N4O2S·CH4O

M = 374.46

Triclinic,

a = 8.8021 (6) Å

b = 9.9949 (10) Å

c = 11.5902 (13) Å

α = 83.132 (1)°

β = 84.179 (2)°

γ = 70.505 (1)°

V = 952.24 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 298 K

0.42 × 0.39 × 0.32 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.923, T max = 0.940

4936 measured reflections

3302 independent reflections

1934 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.01

3302 reflections

239 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 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/S1600536811029035/cv5128sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029035/cv5128Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029035/cv5128Isup3.cml

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

C17H18N4O2S·CH4O	Z = 2
Mr = 374.46	F(000) = 396
Triclinic, P1	Dx = 1.306 Mg m−3
a = 8.8021 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9949 (10) Å	Cell parameters from 1379 reflections
c = 11.5902 (13) Å	θ = 2.7–25.2°
α = 83.132 (1)°	µ = 0.20 mm−1
β = 84.179 (2)°	T = 298 K
γ = 70.505 (1)°	Block, red
V = 952.24 (16) Å3	0.42 × 0.39 × 0.32 mm

Bruker SMART APEX CCD area-detector diffractometer	3302 independent reflections
Radiation source: fine-focus sealed tube	1934 reflections with I > 2σ(I)
graphite	Rint = 0.023
phi and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→10
Tmin = 0.923, Tmax = 0.940	k = −11→11
4936 measured reflections	l = −13→12

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) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.1975P] where P = (Fo2 + 2Fc2)/3
3302 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 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	0.63183 (11)	0.63686 (9)	−0.08592 (7)	0.0604 (3)
N1	0.6991 (3)	0.8790 (2)	−0.00620 (19)	0.0435 (6)
N2	0.6220 (3)	0.8089 (2)	0.07669 (19)	0.0445 (6)
H2	0.5951	0.8368	0.1454	0.053*
N3	0.5206 (3)	0.6273 (2)	0.1308 (2)	0.0487 (7)
H3	0.5021	0.5523	0.1154	0.058*
N4	0.4772 (3)	0.6718 (2)	0.2409 (2)	0.0458 (6)
O1	1.0808 (3)	1.2665 (2)	−0.28491 (19)	0.0653 (7)
O2	0.1682 (3)	0.6793 (2)	0.76724 (19)	0.0688 (7)
C1	0.5902 (3)	0.6955 (3)	0.0468 (2)	0.0424 (7)
C2	0.7256 (3)	0.9876 (3)	0.0215 (2)	0.0412 (7)
H2A	0.6890	1.0203	0.0944	0.049*
C3	0.8135 (3)	1.0612 (3)	−0.0612 (2)	0.0388 (7)
C4	0.8918 (4)	1.0014 (3)	−0.1615 (2)	0.0471 (8)
H4A	0.8839	0.9150	−0.1773	0.057*
C5	0.9813 (4)	1.0662 (3)	−0.2389 (3)	0.0522 (8)
H5	1.0332	1.0239	−0.3057	0.063*
C6	0.9927 (4)	1.1946 (3)	−0.2158 (3)	0.0463 (8)
C7	0.9135 (3)	1.2564 (3)	−0.1173 (3)	0.0473 (8)
H7	0.9189	1.3442	−0.1029	0.057*
C8	0.8264 (3)	1.1902 (3)	−0.0399 (2)	0.0439 (7)
H8	0.7757	1.2323	0.0272	0.053*
C9	1.1754 (5)	1.1998 (4)	−0.3814 (3)	0.0838 (12)
H9A	1.1057	1.1927	−0.4373	0.126*
H9B	1.2437	1.1062	−0.3555	0.126*
H9C	1.2410	1.2554	−0.4168	0.126*
C10	0.3907 (4)	0.6071 (3)	0.3027 (3)	0.0501 (8)
H10	0.3638	0.5391	0.2686	0.060*
C11	0.3309 (4)	0.6312 (3)	0.4222 (2)	0.0458 (8)
C12	0.3712 (4)	0.7200 (3)	0.4869 (3)	0.0589 (9)
H12	0.4377	0.7710	0.4525	0.071*
C13	0.3152 (4)	0.7345 (3)	0.6009 (3)	0.0639 (10)
H13	0.3445	0.7943	0.6433	0.077*
C14	0.2149 (4)	0.6601 (3)	0.6531 (3)	0.0498 (8)
C15	0.1720 (4)	0.5731 (3)	0.5907 (3)	0.0540 (8)
H15	0.1037	0.5236	0.6248	0.065*
C16	0.2307 (4)	0.5589 (3)	0.4766 (3)	0.0573 (9)
H16	0.2017	0.4984	0.4347	0.069*
C17	0.0688 (5)	0.6007 (4)	0.8248 (3)	0.0738 (11)
H17A	0.1258	0.5005	0.8237	0.111*
H17B	−0.0289	0.6249	0.7854	0.111*
H17C	0.0429	0.6239	0.9040	0.111*
O3	0.5382 (3)	0.9498 (3)	−0.2485 (2)	0.0849 (8)
H3A	0.5673	0.8888	−0.1940	0.127*
C18	0.6365 (5)	0.9076 (5)	−0.3470 (3)	0.0884 (13)
H18A	0.5743	0.9401	−0.4144	0.133*
H18B	0.6812	0.8055	−0.3413	0.133*
H18C	0.7224	0.9477	−0.3540	0.133*

	U11	U22	U33	U12	U13	U23
S1	0.0755 (7)	0.0533 (5)	0.0593 (5)	−0.0349 (5)	0.0242 (5)	−0.0148 (4)
N1	0.0458 (15)	0.0437 (14)	0.0427 (14)	−0.0205 (12)	0.0033 (12)	0.0020 (11)
N2	0.0531 (16)	0.0473 (14)	0.0359 (13)	−0.0236 (13)	0.0047 (12)	−0.0001 (11)
N3	0.0550 (16)	0.0413 (14)	0.0514 (15)	−0.0228 (13)	0.0114 (13)	−0.0019 (12)
N4	0.0468 (16)	0.0451 (14)	0.0437 (15)	−0.0162 (13)	0.0036 (12)	0.0016 (12)
O1	0.0743 (16)	0.0593 (14)	0.0680 (15)	−0.0371 (13)	0.0204 (13)	−0.0045 (12)
O2	0.0862 (18)	0.0785 (16)	0.0553 (14)	−0.0468 (14)	0.0218 (13)	−0.0227 (12)
C1	0.0329 (17)	0.0382 (16)	0.0516 (18)	−0.0106 (14)	0.0059 (14)	0.0037 (14)
C2	0.0401 (18)	0.0455 (17)	0.0389 (16)	−0.0152 (14)	−0.0007 (14)	−0.0048 (13)
C3	0.0348 (16)	0.0412 (16)	0.0418 (16)	−0.0138 (13)	−0.0008 (13)	−0.0056 (13)
C4	0.0506 (19)	0.0429 (17)	0.0529 (19)	−0.0220 (15)	0.0043 (16)	−0.0104 (15)
C5	0.059 (2)	0.0518 (19)	0.0490 (18)	−0.0235 (17)	0.0127 (16)	−0.0134 (15)
C6	0.0450 (19)	0.0436 (18)	0.0522 (19)	−0.0202 (15)	−0.0008 (15)	0.0028 (15)
C7	0.0495 (19)	0.0382 (17)	0.0580 (19)	−0.0193 (15)	0.0007 (16)	−0.0082 (15)
C8	0.0434 (18)	0.0430 (17)	0.0474 (18)	−0.0158 (15)	0.0011 (15)	−0.0109 (14)
C9	0.087 (3)	0.075 (3)	0.084 (3)	−0.033 (2)	0.040 (2)	−0.004 (2)
C10	0.056 (2)	0.0481 (18)	0.0496 (19)	−0.0248 (16)	−0.0010 (16)	0.0049 (15)
C11	0.0470 (19)	0.0447 (17)	0.0461 (18)	−0.0194 (15)	0.0039 (15)	0.0011 (14)
C12	0.067 (2)	0.054 (2)	0.065 (2)	−0.0360 (18)	0.0159 (19)	−0.0095 (17)
C13	0.077 (3)	0.060 (2)	0.068 (2)	−0.041 (2)	0.014 (2)	−0.0211 (17)
C14	0.053 (2)	0.0495 (18)	0.0498 (19)	−0.0210 (16)	0.0049 (16)	−0.0088 (15)
C15	0.060 (2)	0.063 (2)	0.0486 (19)	−0.0372 (18)	0.0078 (16)	−0.0024 (16)
C16	0.074 (2)	0.063 (2)	0.049 (2)	−0.0430 (19)	0.0036 (18)	−0.0061 (16)
C17	0.089 (3)	0.092 (3)	0.052 (2)	−0.049 (2)	0.019 (2)	−0.0131 (19)
O3	0.095 (2)	0.0784 (18)	0.0610 (16)	−0.0093 (15)	0.0104 (15)	0.0029 (13)
C18	0.091 (3)	0.115 (3)	0.062 (2)	−0.040 (3)	0.002 (2)	−0.003 (2)

S1—C1	1.673 (3)	C8—H8	0.9300
N1—C2	1.267 (3)	C9—H9A	0.9600
N1—N2	1.377 (3)	C9—H9B	0.9600
N2—C1	1.346 (3)	C9—H9C	0.9600
N2—H2	0.8600	C10—C11	1.449 (4)
N3—C1	1.337 (3)	C10—H10	0.9300
N3—N4	1.377 (3)	C11—C12	1.378 (4)
N3—H3	0.8600	C11—C16	1.379 (4)
N4—C10	1.272 (3)	C12—C13	1.369 (4)
O1—C6	1.367 (3)	C12—H12	0.9300
O1—C9	1.417 (4)	C13—C14	1.385 (4)
O2—C14	1.362 (3)	C13—H13	0.9300
O2—C17	1.429 (4)	C14—C15	1.359 (4)
C2—C3	1.455 (4)	C15—C16	1.376 (4)
C2—H2A	0.9300	C15—H15	0.9300
C3—C4	1.383 (4)	C16—H16	0.9300
C3—C8	1.384 (4)	C17—H17A	0.9600
C4—C5	1.379 (4)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600
C5—C6	1.379 (4)	O3—C18	1.380 (4)
C5—H5	0.9300	O3—H3A	0.8200
C6—C7	1.375 (4)	C18—H18A	0.9600
C7—C8	1.374 (4)	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600
C2—N1—N2	117.7 (2)	O1—C9—H9C	109.5
C1—N2—N1	117.9 (2)	H9A—C9—H9C	109.5
C1—N2—H2	121.0	H9B—C9—H9C	109.5
N1—N2—H2	121.0	N4—C10—C11	125.0 (3)
C1—N3—N4	122.9 (2)	N4—C10—H10	117.5
C1—N3—H3	118.5	C11—C10—H10	117.5
N4—N3—H3	118.5	C12—C11—C16	117.2 (3)
C10—N4—N3	113.5 (3)	C12—C11—C10	124.0 (3)
C6—O1—C9	117.8 (2)	C16—C11—C10	118.7 (3)
C14—O2—C17	117.2 (2)	C13—C12—C11	121.2 (3)
N3—C1—N2	116.1 (3)	C13—C12—H12	119.4
N3—C1—S1	119.4 (2)	C11—C12—H12	119.4
N2—C1—S1	124.5 (2)	C12—C13—C14	120.1 (3)
N1—C2—C3	119.8 (3)	C12—C13—H13	120.0
N1—C2—H2A	120.1	C14—C13—H13	120.0
C3—C2—H2A	120.1	C15—C14—O2	124.4 (3)
C4—C3—C8	118.0 (3)	C15—C14—C13	119.8 (3)
C4—C3—C2	120.8 (3)	O2—C14—C13	115.7 (3)
C8—C3—C2	121.2 (3)	C14—C15—C16	119.2 (3)
C5—C4—C3	121.9 (3)	C14—C15—H15	120.4
C5—C4—H4A	119.0	C16—C15—H15	120.4
C3—C4—H4A	119.0	C15—C16—C11	122.4 (3)
C6—C5—C4	119.1 (3)	C15—C16—H16	118.8
C6—C5—H5	120.4	C11—C16—H16	118.8
C4—C5—H5	120.4	O2—C17—H17A	109.5
O1—C6—C7	116.3 (3)	O2—C17—H17B	109.5
O1—C6—C5	124.1 (3)	H17A—C17—H17B	109.5
C7—C6—C5	119.6 (3)	O2—C17—H17C	109.5
C8—C7—C6	120.9 (3)	H17A—C17—H17C	109.5
C8—C7—H7	119.6	H17B—C17—H17C	109.5
C6—C7—H7	119.6	C18—O3—H3A	109.5
C7—C8—C3	120.5 (3)	O3—C18—H18A	109.5
C7—C8—H8	119.8	O3—C18—H18B	109.5
C3—C8—H8	119.8	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—H3A···N1	0.82	2.55	3.171 (3)	134.
O3—H3A···S1	0.82	2.58	3.346 (3)	156.
N2—H2···O3i	0.86	2.45	3.174 (3)	142.
N3—H3···S1ii	0.86	2.61	3.446 (3)	165.
C2—H2A···O3i	0.93	2.51	3.300 (4)	143.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N1	0.82	2.55	3.171 (3)	134
O3—H3A⋯S1	0.82	2.58	3.346 (3)	156
N2—H2⋯O3i	0.86	2.45	3.174 (3)	142
N3—H3⋯S1ii	0.86	2.61	3.446 (3)	165
C2—H2A⋯O3i	0.93	2.51	3.300 (4)	143

Symmetry codes: (i) ; (ii) .