1,5-Bis(4-meth­oxy­benzyl­idene)thio­carbonohydrazide methanol monosolvate

Zhao, X.

doi:10.1107/S1600536811029035

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2133

doi:10.1107/S1600536811029035

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1,5-Bis(4-methoxybenzylidene)thiocarbonohydrazide methanol monosolvate

Xinyu Zhao ^a ^*

^aSchool of Petrochemical Engineering, Shenyang University of Technology, Liaoyang 111003, People's Republic of China
^*Correspondence e-mail: xyzhaosut@163.com

(Received 27 June 2011; accepted 19 July 2011; online 23 July 2011)

In the title compound, C₁₇H₁₈N₄O₂S·CH₃OH, the two benzene rings in the thiocarbonohydrazide molecule form a dihedral angle of 22.42 (18)°. Pairs of N—H⋯S hydrogen bonds link thiocarbonohydrazide molecules into centrosymmetric dimers. Methanol solvent molecules serve as donors (O—H⋯S and O—H⋯N) and acceptors (N—H⋯O and C—H⋯O) of weak intermolecular 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_r = 374.46
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.137
S = 1.01
3302 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) -x+1, -y+2, -z; (ii) -x+1, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029035/cv5128sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811029035/cv5128Isup3.cml

checkCIF report

Comment top

In recent years, there has been considerable interest in the chemistry of thiocarbohydrazide Schiff base derivatives (Loncle et al., 2004; Camp et al., 2010), because these derivatives offer opportunities for tuning the metal centred electronic factor, enhancing the solubility and stability of either homogeneous or heterogeneous catalysts (Opstal et al., 2003). Herein we present the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene] thiocarbonohydrazide monohydrate (Affan et al., 2010). Four N atoms and the C=S are almost coplanar, the N1/N2/C2 plane and the benzene ring C3–C8 form a dihedral angle of 12.32 (3)°. The benzene rings C3–C8 and C11–C16 form a dihedral angle of 22.42 (18) °.

In the crystal structure, intermolecular N—H···S hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. Solvent molecules serve as donors [O—H···S and O—H···N] and acceptors [N—H···O and C—H···O] of the weak intermolecular hydrogen bonds (Table 1), which link further these dimers into doubled ribbons along axis b.

Related literature top

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 top

4-Methoxybenzaldehyde (10.0 mmol), 30 ml e thanol and thiocarbohydrazide (5.0 mmol) were mixed in 50 ml flash After stirring 3 h at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. View of (I) showing the atomic numbering and 30% probability displacement ellipsoids. Dashed lines denote hydrogen bonds.

1,5-Bis(4-methoxybenzylidene)thiocarbonohydrazide methanol monosolvate top

Crystal data top

C₁₇H₁₈N₄O₂S·CH₄O	Z = 2
M_r = 374.46	F(000) = 396
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3302 independent reflections
Radiation source: fine-focus sealed tube	1934 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
phi and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→10
T_min = 0.923, T_max = 0.940	k = −11→11
4936 measured reflections	l = −13→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) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0585P)² + 0.1975P] where P = (F_o² + 2F_c²)/3
3302 reflections	(Δ/σ)_max < 0.001
239 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₈N₄O₂S·CH₄O	γ = 70.505 (1)°
M_r = 374.46	V = 952.24 (16) Å³
Triclinic, P1	Z = 2
a = 8.8021 (6) Å	Mo Kα radiation
b = 9.9949 (10) Å	µ = 0.20 mm⁻¹
c = 11.5902 (13) Å	T = 298 K
α = 83.132 (1)°	0.42 × 0.39 × 0.32 mm
β = 84.179 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3302 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1934 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.940	R_int = 0.023
4936 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.01	Δρ_max = 0.21 e Å⁻³
3302 reflections	Δρ_min = −0.18 e Å⁻³
239 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	0.63183 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₄O₂S·CH₄O
M_r	374.46
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.8021 (6), 9.9949 (10), 11.5902 (13)
α, β, γ (°)	83.132 (1), 84.179 (2), 70.505 (1)
V (Å³)	952.24 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.42 × 0.39 × 0.32

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.923, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	4936, 3302, 1934
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.137, 1.01
No. of reflections	3302
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N1	0.82	2.55	3.171 (3)	134.1
O3—H3A···S1	0.82	2.58	3.346 (3)	155.6
N2—H2···O3ⁱ	0.86	2.45	3.174 (3)	142.2
N3—H3···S1ⁱⁱ	0.86	2.61	3.446 (3)	164.9
C2—H2A···O3ⁱ	0.93	2.51	3.300 (4)	143.4

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z.

Acknowledgements

The author acknowledges financial support by Shenyang University of Technology.

References

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