Crystal structure of 2-((1E)-{2-[bis­(2-methyl­benzyl­sulfan­yl)methyl­idene]hydrazin-1-yl­idene}meth­yl)-6-meth­oxy­phenol

Yusof, E.N.M.; Ravoof, T.B.S.A.; Tahir, M.I.M.; Tiekink, E.R.T.

doi:10.1107/S2056989015004946

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 4| April 2015| Pages o242-o243

doi:10.1107/S2056989015004946

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Crystal structure of 2-((1E)-{2-[bis(2-methylbenzylsulfanyl)methylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol

Enis Nadia Md Yusof,^a Thahira Begum S. A. Ravoof,^a ^* Mohamed Ibrahim Mohamed Tahir ^a and Edward R. T. Tiekink ^b

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: thahira@upm.edu.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 March 2015; accepted 11 March 2015; online 18 March 2015)

In the title compound, C₂₅H₂₆N₂O₂S₂, the central CN₂S₂ atoms are almost coplanar (r.m.s. deviation = 0.0058 Å). One phenyl ring clearly lies to one side of the central plane, while the other is oriented in the plane but splayed. Despite the different relative orientations, the phenyl rings form similar dihedral angles of 64.90 (3) and 70.06 (3)° with the central plane, and 63.28 (4)° with each other. The benzene ring is twisted with respect to the central plane, forming a dihedral angle of 13.17 (7)°. The S₂C=N, N—N and N—N=C bond lengths of 1.2919 (19), 1.4037 (17) and 1.2892 (19) Å, respectively, suggest limited conjugation over these atoms; the configuration about the N—N=C bond is E. An intramolecular O—H⋯N hydrogen bond is noted. In the crystal, phenyl–methoxy C—H⋯O and phenyl–phenyl C—H⋯π interactions lead to supramolecular double chains parallel to the b axis. These are connected into a layer via methyl–phenyl C—H⋯π interactions, and layers stack along the a axis, being connected by weak π–π interactions between phenyl rings [inter-centroid distance = 3.9915 (9) Å] so that a three-dimensional architecture ensues.

Keywords: crystal structure; S-substituted dithiocarbazates; hydrogen bonding; C—H⋯π interactions; π–π interactions.

CCDC reference: 1053188

1. Related literature

For background to the coordination chemistry of dithiocarbazate derivatives, see: Tarafder et al. (2002 ); Ravoof et al. (2010 , 2011 ); Omar et al. (2014 ). For related synthesis, see: Ali & Tarafder (1977 ); Tarafder et al. (2002); Manan et al. (2012 ). For a related structure but with the S atoms connected by an ethylene bridge, and with a terminal furan-2-yl ring, i.e. N-1,3-dithiolan-2-ylidene-N′-[(E)-furan-2-ylmethylidene]hydrazone, see: Liu et al. (2008 ).

2. Experimental

2.1. Crystal data

C₂₅H₂₆N₂O₂S₂
M_r = 450.60
Monoclinic, P 2₁ /c
a = 19.7865 (7) Å
b = 6.8600 (2) Å
c = 16.1805 (5) Å
β = 94.880 (3)°
V = 2188.31 (12) Å³
Z = 4
Cu Kα radiation
μ = 2.41 mm⁻¹
T = 100 K
0.25 × 0.11 × 0.08 mm

2.2. Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.715, T_max = 1.000
40860 measured reflections
4248 independent reflections
3956 reflections with I > 2σ(I)
R_int = 0.033

2.3. Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.094
S = 1.04
4248 reflections
286 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2	0.84 (2)	1.87 (2)	2.6331 (16)	151 (2)
C5—H5⋯O2ⁱ	0.95	2.44	3.3868 (18)	176
C7—H7⋯Cg1ⁱ	0.95	2.68	3.5046 (15)	146
C9—H9B⋯Cg1ⁱⁱ	0.98	2.72	3.5482 (17)	142
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2015 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1053188

Crystal structure: contains datablocks ml, I. DOI: 10.1107/S2056989015004946/hb7379sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015004946/hb7379Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015004946/hb7379Isup3.cml

checkCIF report

Related literature top

For background to the coordination chemistry of dithiocarbazate derivatives, see: Tarafder et al. (2002); Ravoof et al. (2010, 2011); Omar et al. (2014). For related synthesis, see: Ali & Tarafder (1977); Tarafder et al. (2002); Manan et al. (2012). For a related structure but with the S atoms connected by an ethylene bridge, and with a terminal furan-2-yl ring, i.e. N-1,3-dithiolan-2-ylidene-N'-[(E)-furan-2-ylmethylidene]hydrazone, see: Liu et al. (2008).

Experimental top

The synthesis of S-2-methylbenzyldithiocarbazate (S2MBDTC) was accomplished as reported previously (Ravoof et al., 2011). The title compound was synthesized following an established literature procedure (Ravoof et al., 2011). S2MBDTC (2.12.g, 0.01 mol) was dissolved in hot acetonitrile (150 ml). This was added to an equimolar solution of 2-hydroxy-3-methoxybenzaldehyde (1.52 g, 0.01 mol) in ethanol (20 ml). The mixture was heated and stirred for 30 min and then allowed to stand for a few hours. The yellow crystals formed were filtered off and recrystallized from acetonitrile. Pale-yellow plates were obtained after 1 week by keeping the solution at room temperature.

Structure description top

For background to the coordination chemistry of dithiocarbazate derivatives, see: Tarafder et al. (2002); Ravoof et al. (2010, 2011); Omar et al. (2014). For related synthesis, see: Ali & Tarafder (1977); Tarafder et al. (2002); Manan et al. (2012). For a related structure but with the S atoms connected by an ethylene bridge, and with a terminal furan-2-yl ring, i.e. N-1,3-dithiolan-2-ylidene-N'-[(E)-furan-2-ylmethylidene]hydrazone, see: Liu et al. (2008).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 70% probability level.
	Fig. 2. A view of the unit-cell contents in projection down the b axis. The C—H···O, C—H···π and π—π interactions are shown as orange, purple and pink dashed lines, respectively.

2-((1E)-{2-[Bis(2-methylbenzylsulfanyl)methylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol top

Crystal data top

C₂₅H₂₆N₂O₂S₂	F(000) = 952
M_r = 450.60	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
a = 19.7865 (7) Å	Cell parameters from 17455 reflections
b = 6.8600 (2) Å	θ = 3.4–71.3°
c = 16.1805 (5) Å	µ = 2.41 mm⁻¹
β = 94.880 (3)°	T = 100 K
V = 2188.31 (12) Å³	Plate, pale-yellow
Z = 4	0.25 × 0.11 × 0.08 mm

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	4248 independent reflections
Radiation source: fine-focus sealed tube	3956 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 16.1952 pixels mm^-1	θ_max = 71.4°, θ_min = 4.5°
ω scans	h = −24→24
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→8
T_min = 0.715, T_max = 1.000	l = −19→19
40860 measured reflections

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0589P)² + 0.9765P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4248 reflections	Δρ_max = 0.41 e Å⁻³
286 parameters	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₅H₂₆N₂O₂S₂	V = 2188.31 (12) Å³
M_r = 450.60	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 19.7865 (7) Å	µ = 2.41 mm⁻¹
b = 6.8600 (2) Å	T = 100 K
c = 16.1805 (5) Å	0.25 × 0.11 × 0.08 mm
β = 94.880 (3)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	4248 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3956 reflections with I > 2σ(I)
T_min = 0.715, T_max = 1.000	R_int = 0.033
40860 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.41 e Å⁻³
4248 reflections	Δρ_min = −0.24 e Å⁻³
286 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.31760 (2)	0.15598 (5)	0.33906 (2)	0.01851 (11)
S2	0.22443 (2)	0.01673 (5)	0.46350 (2)	0.01756 (11)
O1	0.29427 (6)	0.56093 (16)	0.18572 (7)	0.0234 (2)
H1O	0.2807 (10)	0.492 (3)	0.2236 (10)	0.035*
O2	0.32372 (5)	0.83198 (15)	0.08026 (7)	0.0220 (2)
N1	0.19930 (6)	0.32696 (18)	0.36803 (7)	0.0176 (3)
N2	0.22172 (6)	0.44896 (18)	0.30629 (7)	0.0173 (3)
C1	0.24117 (7)	0.1860 (2)	0.38658 (8)	0.0159 (3)
C2	0.36133 (8)	−0.0340 (2)	0.40266 (10)	0.0219 (3)
H2A	0.3653	0.0069	0.4615	0.026*
H2B	0.3345	−0.1559	0.3981	0.026*
C3	0.43130 (7)	−0.0713 (2)	0.37492 (9)	0.0184 (3)
C4	0.48507 (8)	0.0607 (2)	0.39319 (9)	0.0179 (3)
C5	0.54953 (8)	0.0092 (2)	0.37141 (9)	0.0191 (3)
H5	0.5862	0.0971	0.3829	0.023*
C6	0.56105 (8)	−0.1674 (2)	0.33335 (9)	0.0205 (3)
H6	0.6055	−0.2002	0.3200	0.025*
C7	0.50798 (8)	−0.2964 (2)	0.31473 (9)	0.0214 (3)
H7	0.5157	−0.4175	0.2886	0.026*
C8	0.44318 (8)	−0.2458 (2)	0.33495 (9)	0.0210 (3)
H8	0.4064	−0.3322	0.3212	0.025*
C9	0.47480 (8)	0.2536 (2)	0.43450 (10)	0.0229 (3)
H9A	0.5178	0.3254	0.4400	0.034*
H9B	0.4592	0.2315	0.4896	0.034*
H9C	0.4407	0.3296	0.4008	0.034*
C10	0.14184 (7)	0.0968 (2)	0.49331 (9)	0.0180 (3)
H10A	0.1365	0.0506	0.5503	0.022*
H10B	0.1411	0.2411	0.4943	0.022*
C11	0.08218 (7)	0.0259 (2)	0.43695 (9)	0.0180 (3)
C12	0.06032 (7)	−0.1688 (2)	0.43911 (9)	0.0189 (3)
C13	0.00459 (8)	−0.2245 (2)	0.38554 (9)	0.0228 (3)
H13	−0.0107	−0.3558	0.3861	0.027*
C14	−0.02900 (8)	−0.0927 (3)	0.33158 (10)	0.0249 (3)
H14	−0.0664	−0.1344	0.2952	0.030*
C15	−0.00799 (8)	0.1002 (2)	0.33070 (9)	0.0232 (3)
H15	−0.0314	0.1917	0.2947	0.028*
C16	0.04763 (8)	0.1581 (2)	0.38300 (9)	0.0201 (3)
H16	0.0624	0.2897	0.3821	0.024*
C17	0.09534 (8)	−0.3151 (2)	0.49745 (9)	0.0227 (3)
H17A	0.0692	−0.4366	0.4955	0.034*
H17B	0.0987	−0.2631	0.5540	0.034*
H17C	0.1410	−0.3409	0.4808	0.034*
C18	0.18647 (7)	0.6061 (2)	0.29468 (9)	0.0171 (3)
H18	0.1490	0.6274	0.3267	0.020*
C19	0.20239 (7)	0.7516 (2)	0.23404 (8)	0.0168 (3)
C20	0.25580 (7)	0.7241 (2)	0.18293 (9)	0.0178 (3)
C21	0.27077 (7)	0.8714 (2)	0.12674 (9)	0.0179 (3)
C22	0.23361 (8)	1.0427 (2)	0.12261 (9)	0.0193 (3)
H22	0.2443	1.1429	0.0853	0.023*
C23	0.18044 (8)	1.0686 (2)	0.17308 (9)	0.0203 (3)
H23	0.1549	1.1860	0.1694	0.024*
C24	0.16474 (7)	0.9262 (2)	0.22791 (9)	0.0190 (3)
H24	0.1284	0.9453	0.2618	0.023*
C25	0.33745 (8)	0.9728 (2)	0.01891 (10)	0.0223 (3)
H25A	0.2976	0.9870	−0.0209	0.034*
H25B	0.3762	0.9296	−0.0103	0.034*
H25C	0.3480	1.0985	0.0458	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01353 (19)	0.0233 (2)	0.01915 (19)	0.00182 (13)	0.00389 (13)	0.00516 (13)
S2	0.01378 (19)	0.02052 (19)	0.01875 (19)	0.00014 (13)	0.00349 (13)	0.00367 (13)
O1	0.0240 (6)	0.0197 (5)	0.0281 (6)	0.0072 (4)	0.0118 (5)	0.0080 (5)
O2	0.0203 (5)	0.0228 (5)	0.0240 (5)	0.0052 (4)	0.0079 (4)	0.0076 (4)
N1	0.0168 (6)	0.0180 (6)	0.0184 (6)	−0.0019 (5)	0.0030 (5)	0.0006 (5)
N2	0.0157 (6)	0.0186 (6)	0.0179 (6)	−0.0006 (5)	0.0030 (5)	0.0015 (5)
C1	0.0133 (7)	0.0191 (7)	0.0155 (6)	−0.0036 (5)	0.0018 (5)	−0.0015 (5)
C2	0.0162 (7)	0.0242 (8)	0.0257 (8)	0.0031 (6)	0.0036 (6)	0.0093 (6)
C3	0.0150 (7)	0.0232 (7)	0.0171 (7)	0.0017 (6)	0.0018 (5)	0.0063 (6)
C4	0.0190 (7)	0.0200 (7)	0.0149 (6)	0.0005 (6)	0.0020 (5)	0.0033 (5)
C5	0.0165 (7)	0.0234 (8)	0.0174 (7)	−0.0019 (6)	0.0016 (6)	0.0038 (6)
C6	0.0163 (7)	0.0281 (8)	0.0178 (7)	0.0037 (6)	0.0047 (6)	0.0039 (6)
C7	0.0246 (8)	0.0217 (7)	0.0182 (7)	0.0026 (6)	0.0034 (6)	−0.0007 (6)
C8	0.0193 (7)	0.0222 (7)	0.0210 (7)	−0.0030 (6)	−0.0002 (6)	0.0020 (6)
C9	0.0223 (8)	0.0225 (8)	0.0239 (7)	0.0012 (6)	0.0015 (6)	−0.0004 (6)
C10	0.0144 (7)	0.0224 (7)	0.0180 (7)	−0.0001 (6)	0.0057 (5)	−0.0016 (6)
C11	0.0137 (7)	0.0234 (7)	0.0178 (7)	0.0010 (6)	0.0069 (5)	−0.0021 (6)
C12	0.0173 (7)	0.0230 (7)	0.0175 (7)	0.0016 (6)	0.0077 (6)	−0.0006 (6)
C13	0.0202 (8)	0.0249 (8)	0.0243 (8)	−0.0039 (6)	0.0076 (6)	−0.0024 (6)
C14	0.0150 (7)	0.0377 (9)	0.0223 (7)	−0.0048 (7)	0.0032 (6)	−0.0017 (7)
C15	0.0171 (7)	0.0309 (8)	0.0223 (7)	0.0046 (6)	0.0051 (6)	0.0053 (6)
C16	0.0178 (7)	0.0208 (7)	0.0228 (7)	0.0008 (6)	0.0075 (6)	0.0007 (6)
C17	0.0238 (8)	0.0217 (7)	0.0233 (7)	−0.0002 (6)	0.0054 (6)	0.0020 (6)
C18	0.0131 (7)	0.0213 (7)	0.0168 (7)	−0.0009 (5)	0.0017 (5)	−0.0029 (6)
C19	0.0152 (7)	0.0183 (7)	0.0164 (7)	−0.0007 (5)	−0.0004 (5)	−0.0020 (5)
C20	0.0150 (7)	0.0178 (7)	0.0202 (7)	0.0022 (5)	0.0001 (5)	−0.0006 (6)
C21	0.0156 (7)	0.0206 (7)	0.0174 (7)	0.0007 (6)	0.0004 (5)	−0.0004 (6)
C22	0.0198 (7)	0.0190 (7)	0.0185 (7)	0.0007 (6)	−0.0012 (6)	0.0031 (6)
C23	0.0198 (7)	0.0182 (7)	0.0224 (7)	0.0050 (6)	−0.0022 (6)	−0.0015 (6)
C24	0.0148 (7)	0.0227 (8)	0.0192 (7)	0.0025 (6)	0.0010 (5)	−0.0037 (6)
C25	0.0237 (8)	0.0219 (8)	0.0221 (7)	−0.0005 (6)	0.0056 (6)	0.0048 (6)

Geometric parameters (Å, º) top

S1—C1	1.7658 (14)	C10—H10B	0.9900
S1—C2	1.8317 (15)	C11—C16	1.396 (2)
S2—C1	1.7543 (14)	C11—C12	1.405 (2)
S2—C10	1.8271 (14)	C12—C13	1.397 (2)
O1—C20	1.3519 (18)	C12—C17	1.506 (2)
O1—H1O	0.835 (9)	C13—C14	1.387 (2)
O2—C21	1.3676 (18)	C13—H13	0.9500
O2—C25	1.4279 (18)	C14—C15	1.387 (2)
N1—C1	1.2919 (19)	C14—H14	0.9500
N1—N2	1.4037 (17)	C15—C16	1.388 (2)
N2—C18	1.2892 (19)	C15—H15	0.9500
C2—C3	1.513 (2)	C16—H16	0.9500
C2—H2A	0.9900	C17—H17A	0.9800
C2—H2B	0.9900	C17—H17B	0.9800
C3—C8	1.390 (2)	C17—H17C	0.9800
C3—C4	1.409 (2)	C18—C19	1.453 (2)
C4—C5	1.397 (2)	C18—H18	0.9500
C4—C9	1.504 (2)	C19—C20	1.409 (2)
C5—C6	1.387 (2)	C19—C24	1.409 (2)
C5—H5	0.9500	C20—C21	1.408 (2)
C6—C7	1.387 (2)	C21—C22	1.385 (2)
C6—H6	0.9500	C22—C23	1.397 (2)
C7—C8	1.394 (2)	C22—H22	0.9500
C7—H7	0.9500	C23—C24	1.373 (2)
C8—H8	0.9500	C23—H23	0.9500
C9—H9A	0.9800	C24—H24	0.9500
C9—H9B	0.9800	C25—H25A	0.9800
C9—H9C	0.9800	C25—H25B	0.9800
C10—C11	1.509 (2)	C25—H25C	0.9800
C10—H10A	0.9900

C1—S1—C2	102.68 (7)	C13—C12—C11	118.25 (14)
C1—S2—C10	102.44 (7)	C13—C12—C17	120.22 (14)
C20—O1—H1O	105.9 (14)	C11—C12—C17	121.53 (14)
C21—O2—C25	116.65 (11)	C14—C13—C12	121.52 (15)
C1—N1—N2	112.11 (12)	C14—C13—H13	119.2
C18—N2—N1	113.74 (12)	C12—C13—H13	119.2
N1—C1—S2	120.28 (11)	C13—C14—C15	120.04 (14)
N1—C1—S1	122.83 (11)	C13—C14—H14	120.0
S2—C1—S1	116.88 (8)	C15—C14—H14	120.0
C3—C2—S1	110.74 (10)	C14—C15—C16	119.30 (14)
C3—C2—H2A	109.5	C14—C15—H15	120.3
S1—C2—H2A	109.5	C16—C15—H15	120.3
C3—C2—H2B	109.5	C15—C16—C11	121.05 (14)
S1—C2—H2B	109.5	C15—C16—H16	119.5
H2A—C2—H2B	108.1	C11—C16—H16	119.5
C8—C3—C4	119.77 (13)	C12—C17—H17A	109.5
C8—C3—C2	118.61 (13)	C12—C17—H17B	109.5
C4—C3—C2	121.50 (14)	H17A—C17—H17B	109.5
C5—C4—C3	118.28 (14)	C12—C17—H17C	109.5
C5—C4—C9	119.68 (13)	H17A—C17—H17C	109.5
C3—C4—C9	122.04 (13)	H17B—C17—H17C	109.5
C6—C5—C4	121.39 (14)	N2—C18—C19	121.81 (13)
C6—C5—H5	119.3	N2—C18—H18	119.1
C4—C5—H5	119.3	C19—C18—H18	119.1
C7—C6—C5	120.27 (14)	C20—C19—C24	119.42 (13)
C7—C6—H6	119.9	C20—C19—C18	121.40 (13)
C5—C6—H6	119.9	C24—C19—C18	119.16 (13)
C6—C7—C8	119.00 (14)	O1—C20—C21	117.85 (13)
C6—C7—H7	120.5	O1—C20—C19	122.66 (13)
C8—C7—H7	120.5	C21—C20—C19	119.49 (13)
C3—C8—C7	121.26 (14)	O2—C21—C22	124.72 (13)
C3—C8—H8	119.4	O2—C21—C20	115.23 (13)
C7—C8—H8	119.4	C22—C21—C20	120.03 (13)
C4—C9—H9A	109.5	C21—C22—C23	120.19 (14)
C4—C9—H9B	109.5	C21—C22—H22	119.9
H9A—C9—H9B	109.5	C23—C22—H22	119.9
C4—C9—H9C	109.5	C24—C23—C22	120.68 (14)
H9A—C9—H9C	109.5	C24—C23—H23	119.7
H9B—C9—H9C	109.5	C22—C23—H23	119.7
C11—C10—S2	114.51 (10)	C23—C24—C19	120.18 (13)
C11—C10—H10A	108.6	C23—C24—H24	119.9
S2—C10—H10A	108.6	C19—C24—H24	119.9
C11—C10—H10B	108.6	O2—C25—H25A	109.5
S2—C10—H10B	108.6	O2—C25—H25B	109.5
H10A—C10—H10B	107.6	H25A—C25—H25B	109.5
C16—C11—C12	119.83 (14)	O2—C25—H25C	109.5
C16—C11—C10	118.98 (14)	H25A—C25—H25C	109.5
C12—C11—C10	121.18 (13)	H25B—C25—H25C	109.5

C1—N1—N2—C18	−170.55 (13)	C10—C11—C12—C17	−0.1 (2)
N2—N1—C1—S2	179.01 (10)	C11—C12—C13—C14	−0.3 (2)
N2—N1—C1—S1	0.46 (17)	C17—C12—C13—C14	179.51 (14)
C10—S2—C1—N1	2.58 (13)	C12—C13—C14—C15	−0.8 (2)
C10—S2—C1—S1	−178.79 (8)	C13—C14—C15—C16	1.3 (2)
C2—S1—C1—N1	169.89 (12)	C14—C15—C16—C11	−0.7 (2)
C2—S1—C1—S2	−8.71 (10)	C12—C11—C16—C15	−0.4 (2)
C1—S1—C2—C3	−176.06 (11)	C10—C11—C16—C15	−179.26 (13)
S1—C2—C3—C8	−109.37 (14)	N1—N2—C18—C19	179.27 (12)
S1—C2—C3—C4	74.54 (16)	N2—C18—C19—C20	2.3 (2)
C8—C3—C4—C5	−1.1 (2)	N2—C18—C19—C24	−175.95 (13)
C2—C3—C4—C5	174.96 (13)	C24—C19—C20—O1	179.65 (13)
C8—C3—C4—C9	178.52 (13)	C18—C19—C20—O1	1.4 (2)
C2—C3—C4—C9	−5.4 (2)	C24—C19—C20—C21	0.1 (2)
C3—C4—C5—C6	−0.5 (2)	C18—C19—C20—C21	−178.11 (13)
C9—C4—C5—C6	179.90 (13)	C25—O2—C21—C22	−5.1 (2)
C4—C5—C6—C7	1.1 (2)	C25—O2—C21—C20	176.10 (13)
C5—C6—C7—C8	−0.1 (2)	O1—C20—C21—O2	0.0 (2)
C4—C3—C8—C7	2.1 (2)	C19—C20—C21—O2	179.55 (12)
C2—C3—C8—C7	−174.06 (13)	O1—C20—C21—C22	−178.84 (13)
C6—C7—C8—C3	−1.5 (2)	C19—C20—C21—C22	0.7 (2)
C1—S2—C10—C11	82.27 (12)	O2—C21—C22—C23	−179.84 (14)
S2—C10—C11—C16	−106.83 (14)	C20—C21—C22—C23	−1.1 (2)
S2—C10—C11—C12	74.37 (15)	C21—C22—C23—C24	0.7 (2)
C16—C11—C12—C13	0.9 (2)	C22—C23—C24—C19	0.2 (2)
C10—C11—C12—C13	179.73 (13)	C20—C19—C24—C23	−0.6 (2)
C16—C11—C12—C17	−178.88 (13)	C18—C19—C24—C23	177.71 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.84 (2)	1.87 (2)	2.6331 (16)	151 (2)
C5—H5···O2ⁱ	0.95	2.44	3.3868 (18)	176
C7—H7···Cg1ⁱ	0.95	2.68	3.5046 (15)	146
C9—H9B···Cg1ⁱⁱ	0.98	2.72	3.5482 (17)	142

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.836 (18)	1.872 (18)	2.6331 (16)	151 (2)
C5—H5···O2ⁱ	0.95	2.44	3.3868 (18)	176
C7—H7···Cg1ⁱ	0.95	2.68	3.5046 (15)	146
C9—H9B···Cg1ⁱⁱ	0.98	2.72	3.5482 (17)	142

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

Acknowledgements

We thank the Department of Chemistry, Universiti Putra Malaysia for facilities. This research was funded by Universiti Putra Malaysia (UPM) and the Malaysian Government under the Geran UPM Scheme (RUGS No. IBT/2013/9419400), the Malaysian Fundamental Research Grant Scheme (FRGS No. 01–02-13–1344FR) and the ScienceFund under the Ministry of Science, Technology and Innovation (MOSTI 06–01-04-SF1810). ENMY wishes to thank UPM for the award of a Graduate Research Fellowship.

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Volume 71| Part 4| April 2015| Pages o242-o243

doi:10.1107/S2056989015004946

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-((1E)-{2-[bis­­(2-methyl­benzyl­sulfan­yl)methyl­­idene]hydrazin-1-yl­­idene}meth­yl)-6-meth­­oxy­phenol

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-((1E)-{2-[bis(2-methylbenzylsulfanyl)methylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol