Methyl 2-{2-[(E)-(2-hy­droxy-3-meth­oxy­benzyl­idene)amino]­ethyl­amino}­cyclo­pentene-1-carbodithio­ate

Menati, S.; Kakanejadi, A.; Taeb, A.; Bruno, G.; Amiri Rudbari, H.

doi:10.1107/S1600536811002972

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o535

doi:10.1107/S1600536811002972

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Methyl 2-{2-[(E)-(2-hydroxy-3-methoxybenzylidene)amino]ethylamino}cyclopentene-1-carbodithioate

Saeid Menati,^a ^* Ali Kakanejadi,^b Abbas Taeb,^a Giuseppe Bruno ^c and Hadi Amiri Rudbari ^c

^aDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^bDepartment of Chemistry, University of Lorestan, Lorestan, Iran, and ^cDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Universita di Messina, 98166 Messina, Italy
^*Correspondence e-mail: saiedmenati@gmail.com

(Received 19 January 2011; accepted 22 January 2011; online 29 January 2011)

In the title Schiff base compound, C₁₇H₂₂N₂O₂S₂, which adopts an E configuration with respect to the imine C=N double bond, the C=N and N—C bond distances are 1.2789 (16) and 1.4546 (16) Å, respectively. In the molecule there are intramolecular O—H⋯N and N—H⋯S hydrogen bonds, and the CH=N—C substituent is almost coplanar with the benzene ring [C—N—C—C torsion angle = −178.80 (11)°]. The crystal packing is stabilized by intermolecular C—H⋯O and C—H⋯π interactions involving the aromatic ring.

Related literature

For properties and applications of Schiff base compounds, see: Sabater et al. (1999 ); Di Bella & Fragala (2002 ); Lecren et al. (2007 ); Güngör & Gürkan (2010 ). For related structures, see: Pereira et al. (2008 ); Kumar et al. (1995 ); Asadi et al. (2009 ).

Experimental

Crystal data

C₁₇H₂₂N₂O₂S₂
M_r = 350.49
Triclinic, $[P \overline 1]$
a = 7.7933 (2) Å
b = 10.3486 (2) Å
c = 11.9532 (3) Å
α = 108.038 (1)°
β = 93.349 (1)°
γ = 100.296 (1)°
V = 895.19 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.56 × 0.45 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.678, T_max = 0.746
34525 measured reflections
4761 independent reflections
4235 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.109
S = 1.05
4761 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2	0.86	2.32	3.0275 (11)	140
O2—H2⋯N2	0.82	1.85	2.5806 (14)	147
C9—H9B⋯O2ⁱ	0.97	2.51	3.1166 (16)	120
C1—H1C⋯Cgⁱⁱ	0.96	2.95	3.617 (2)	128
Symmetry codes: (i) -x, -y+2, -z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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 global, I. DOI: 10.1107/S1600536811002972/su2251sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002972/su2251Isup2.hkl

checkCIF report

Comment top

Reflecting their usual relative ease of synthesis and excellent imine bonding properties, Schiff base compounds have been extensively investigated for more than a century. They have been employed in areas that include analytical and bioinorganic chemistry, non-linear optics, fluorescence studies, catalysis and materials chemistry (Sabater et al., 1999; Di Bella et al., 2002; Lecren et al., 2007). The development of simple methods to produce asymmetric products remains an area of considerable research activity (Güngör et al., 2010). In the other hand, it is well known that N and S atoms play a key role in the coordination of metals at the active sites of numerous metallobiomolecules. We are particularly interested in the synthesis and characterization of such asymmetric Schiff base compounds.

Three new asymmetric Schiff base compounds, (E)-methyl 2-(2-(2-hydroxy-3-methoxybenzylideneamino)ethylamino)cyclopent-1- enecarbodithioate (1), (E)-methyl 2-(2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)ethylamino) cyclopent-1-enecarbodithioate (2) and (E)-methyl 2-(2-(3-hydroxy-4-methoxybenzylideneamino)ethylamino) cyclopent-1- enecarbodithioate (3) have been prepared. Herein we report on the crystal structure of compound (1).

The molecular structure of compound (1) (Fig. 1) is similar to those of analogous derivatives (Pereira et al., 2008; Kumar et al., 1995; Asadi et al., 2009). The title molecule adopts an E configuration with respect to the imine C═N double bond, with a C11—C10—N2—C9 torsion angle of -178.80 (11)°. The C12—O2 bond distance of 1.3377 (15) Å suggests that it is the phenol-imine tautomer. The contraction of the C10═N2 bond [1.2789 (16) Å] is also in agreement with the phenol-imine tautomer. As for the methoxy group, the O1—C13 and O1—C17 bond distances are 1.365 (2) and 1.420 (2) Å, respectively, and the C13—O1—C17 bond angle is 116.50 (17) Å. The planarity of the molecule is stabilized by intramolecular O—H···N and N–H···S hydrogen bonds (Fig. 1 and Table 1). However, there are no intermolecular hydrogen bonds associated with the methoxy group.

The crystal packing in compound (1) is stabilized by C—H···O and C—H···π interactions; the later involving the aromatic ring (C11—C16) and the C1—H1C H-atom (Fig. 2 and Table 1).

Related literature top

For properties and applications of Schiff base compounds, see: Sabater et al. (1999); Di Bella et al. (2002); Lecren et al. (2007); Güngör et al. (2010). For related structures, see: Pereira et al. (2008); Kumar et al. (1995); Asadi et al. (2009).

Experimental top

Methyl-2-{N-(2-aminoethane)}-amino-1-cyclopentenedithiocarboxylate (Hcden) was prepared by literature methods. The compounds (1), (2) and (3) were prepared by the addition of an equimolar amount of a methanolic solution of the appropriate benzaldehydr, 2-hydroxy-3-methoxybenzaldehyde, 3,5-di-tert-butyl-2-hydroxybenzaldehyde and 3-hydroxy-4-methoxybenzaldehyde, respectively, to a methanolic solution of Hcden. The products obtained were recrystallized from methanol/chloroform 1:1 (V:V).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. Molecular structure of the compound (1), with displacement ellipsoids drawn at the 50% probability level. The intramolecular N—H···S and O—H···N hydrogen bonds are shown as dashed lines.
	Fig. 2. A view of the crystal packing of compound (1), with the C—H···O and the C–H···π interactions shown as dotted lines [see Table 1 for details; H-atoms not involved in these interactions have been omitted for clarity].

Methyl 2-{2-[(E)-(2-hydroxy-3- methoxybenzylidene)amino]ethylamino}cyclopentene-1-carbodithioate top

Crystal data top

C₁₇H₂₂N₂O₂S₂	Z = 2
M_r = 350.49	F(000) = 372
Triclinic, P1	D_x = 1.300 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7933 (2) Å	Cell parameters from 9856 reflections
b = 10.3486 (2) Å	θ = 2.7–29.0°
c = 11.9532 (3) Å	µ = 0.31 mm⁻¹
α = 108.038 (1)°	T = 296 K
β = 93.349 (1)°	Prismatic, black
γ = 100.296 (1)°	0.56 × 0.45 × 0.34 mm
V = 895.19 (4) Å³

Data collection top

Bruker APEXII CCD diffractometer	4761 independent reflections
Radiation source: fine-focus sealed tube	4235 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 29.1°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.678, T_max = 0.746	k = −14→14
34525 measured reflections	l = −16→16

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0602P)² + 0.160P] where P = (F_o² + 2F_c²)/3
4761 reflections	(Δ/σ)_max = 0.002
211 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₇H₂₂N₂O₂S₂	γ = 100.296 (1)°
M_r = 350.49	V = 895.19 (4) Å³
Triclinic, P1	Z = 2
a = 7.7933 (2) Å	Mo Kα radiation
b = 10.3486 (2) Å	µ = 0.31 mm⁻¹
c = 11.9532 (3) Å	T = 296 K
α = 108.038 (1)°	0.56 × 0.45 × 0.34 mm
β = 93.349 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4761 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4235 reflections with I > 2σ(I)
T_min = 0.678, T_max = 0.746	R_int = 0.019
34525 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
4761 reflections	Δρ_min = −0.23 e Å⁻³
211 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.34940 (5)	0.35488 (3)	0.20000 (3)	0.05017 (11)
S2	0.29009 (5)	0.64159 (4)	0.22423 (3)	0.05473 (11)
O1	−0.09386 (17)	1.17333 (16)	0.37397 (12)	0.0836 (4)
O2	0.00507 (12)	1.04545 (10)	0.17106 (8)	0.0511 (2)
H2	0.0495	1.0077	0.1123	0.077*
N1	0.21120 (14)	0.62955 (11)	−0.03025 (9)	0.0435 (2)
H1	0.2184	0.6727	0.0445	0.052*
N2	0.23401 (13)	0.92834 (10)	0.05271 (10)	0.0433 (2)
C1	0.3828 (3)	0.4423 (2)	0.35518 (14)	0.0785 (5)
H1A	0.4744	0.5239	0.3731	0.118*
H1B	0.4162	0.3817	0.3953	0.118*
H1C	0.2761	0.4687	0.3810	0.118*
C2	0.29524 (14)	0.47869 (11)	0.13773 (10)	0.0375 (2)
C3	0.26114 (14)	0.42536 (11)	0.01462 (10)	0.0365 (2)
C4	0.22487 (13)	0.49886 (11)	−0.06190 (9)	0.0360 (2)
C5	0.20752 (18)	0.40864 (13)	−0.18882 (10)	0.0465 (3)
H5A	0.3113	0.4324	−0.2252	0.056*
H5B	0.1054	0.4178	−0.2339	0.056*
C6	0.1871 (2)	0.26237 (15)	−0.18208 (13)	0.0625 (4)
H6A	0.2465	0.2067	−0.2422	0.075*
H6B	0.0639	0.2176	−0.1938	0.075*
C7	0.2702 (2)	0.27904 (13)	−0.05846 (11)	0.0503 (3)
H7A	0.2050	0.2117	−0.0272	0.060*
H7B	0.3911	0.2676	−0.0596	0.060*
C8	0.18503 (17)	0.70860 (13)	−0.10912 (11)	0.0461 (3)
H8A	0.0618	0.7121	−0.1197	0.055*
H8B	0.2189	0.6634	−0.1861	0.055*
C9	0.29423 (16)	0.85464 (13)	−0.05752 (12)	0.0453 (3)
H9A	0.4167	0.8509	−0.0428	0.054*
H9B	0.2850	0.9041	−0.1138	0.054*
C10	0.33243 (16)	0.95933 (13)	0.15062 (12)	0.0454 (3)
H10	0.4421	0.9356	0.1493	0.054*
C11	0.27848 (17)	1.03029 (12)	0.26352 (11)	0.0461 (3)
C12	0.11586 (17)	1.06993 (12)	0.26856 (11)	0.0449 (3)
C13	0.0665 (2)	1.13836 (16)	0.37903 (14)	0.0592 (3)
C14	0.1797 (3)	1.16566 (19)	0.48081 (14)	0.0744 (5)
H14	0.1466	1.2100	0.5541	0.089*
C15	0.3412 (3)	1.1281 (2)	0.47537 (15)	0.0780 (5)
H15	0.4165	1.1487	0.5447	0.094*
C16	0.3908 (2)	1.06093 (17)	0.36880 (15)	0.0652 (4)
H16	0.4993	1.0353	0.3658	0.078*
C17	−0.1453 (3)	1.2484 (3)	0.4833 (2)	0.1217 (11)
H17A	−0.1475	1.1949	0.5363	0.183*
H17B	−0.2603	1.2659	0.4696	0.183*
H17C	−0.0630	1.3351	0.5180	0.183*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0626 (2)	0.04592 (18)	0.04539 (17)	0.01308 (14)	0.00025 (14)	0.01981 (13)
S2	0.0818 (3)	0.04600 (18)	0.03766 (16)	0.02337 (16)	0.00973 (15)	0.00942 (13)
O1	0.0729 (7)	0.0936 (10)	0.0702 (8)	0.0283 (7)	0.0167 (6)	−0.0007 (7)
O2	0.0478 (5)	0.0523 (5)	0.0496 (5)	0.0163 (4)	−0.0034 (4)	0.0101 (4)
N1	0.0560 (6)	0.0407 (5)	0.0373 (5)	0.0170 (4)	0.0067 (4)	0.0138 (4)
N2	0.0452 (5)	0.0389 (5)	0.0488 (5)	0.0130 (4)	0.0043 (4)	0.0167 (4)
C1	0.1227 (16)	0.0735 (11)	0.0439 (7)	0.0214 (10)	0.0018 (9)	0.0266 (7)
C2	0.0363 (5)	0.0385 (5)	0.0389 (5)	0.0075 (4)	0.0053 (4)	0.0142 (4)
C3	0.0356 (5)	0.0345 (5)	0.0381 (5)	0.0071 (4)	0.0032 (4)	0.0105 (4)
C4	0.0321 (4)	0.0382 (5)	0.0369 (5)	0.0070 (4)	0.0033 (4)	0.0112 (4)
C5	0.0549 (7)	0.0438 (6)	0.0359 (5)	0.0074 (5)	−0.0013 (5)	0.0088 (5)
C6	0.0919 (11)	0.0417 (7)	0.0447 (7)	0.0121 (7)	−0.0077 (7)	0.0050 (5)
C7	0.0654 (8)	0.0371 (6)	0.0449 (6)	0.0130 (5)	−0.0009 (5)	0.0085 (5)
C8	0.0547 (6)	0.0463 (6)	0.0427 (6)	0.0181 (5)	0.0050 (5)	0.0183 (5)
C9	0.0466 (6)	0.0467 (6)	0.0522 (7)	0.0177 (5)	0.0123 (5)	0.0240 (5)
C10	0.0434 (6)	0.0392 (6)	0.0575 (7)	0.0114 (4)	0.0007 (5)	0.0208 (5)
C11	0.0531 (6)	0.0378 (5)	0.0486 (6)	0.0098 (5)	−0.0049 (5)	0.0174 (5)
C12	0.0517 (6)	0.0365 (5)	0.0459 (6)	0.0074 (5)	0.0000 (5)	0.0146 (5)
C13	0.0685 (9)	0.0524 (7)	0.0531 (8)	0.0121 (6)	0.0091 (6)	0.0119 (6)
C14	0.1066 (14)	0.0683 (10)	0.0437 (7)	0.0165 (10)	0.0050 (8)	0.0136 (7)
C15	0.1076 (14)	0.0729 (11)	0.0508 (8)	0.0220 (10)	−0.0196 (9)	0.0196 (8)
C16	0.0735 (9)	0.0595 (8)	0.0619 (9)	0.0192 (7)	−0.0176 (7)	0.0202 (7)
C17	0.0930 (15)	0.127 (2)	0.1020 (17)	0.0243 (15)	0.0333 (13)	−0.0292 (16)

Geometric parameters (Å, º) top

S1—C2	1.7666 (11)	C6—H6A	0.9700
S1—C1	1.7740 (16)	C6—H6B	0.9700
S2—C2	1.6918 (12)	C7—H7A	0.9700
O1—C13	1.365 (2)	C7—H7B	0.9700
O1—C17	1.420 (2)	C8—C9	1.5134 (18)
O2—C12	1.3377 (15)	C8—H8A	0.9700
O2—H2	0.8201	C8—H8B	0.9700
N1—C4	1.3126 (15)	C9—H9A	0.9700
N1—C8	1.4541 (15)	C9—H9B	0.9700
N1—H1	0.8595	C10—C11	1.4493 (19)
N2—C10	1.2789 (16)	C10—H10	0.9300
N2—C9	1.4546 (16)	C11—C12	1.3991 (18)
C1—H1A	0.9600	C11—C16	1.4055 (18)
C1—H1B	0.9600	C12—C13	1.4037 (19)
C1—H1C	0.9600	C13—C14	1.382 (2)
C2—C3	1.3926 (15)	C14—C15	1.381 (3)
C3—C4	1.4046 (15)	C14—H14	0.9300
C3—C7	1.5124 (16)	C15—C16	1.364 (3)
C4—C5	1.4984 (15)	C15—H15	0.9300
C5—C6	1.521 (2)	C16—H16	0.9300
C5—H5A	0.9700	C17—H17A	0.9600
C5—H5B	0.9700	C17—H17B	0.9600
C6—C7	1.5243 (19)	C17—H17C	0.9600

C2—S1—C1	104.65 (7)	N1—C8—C9	109.96 (10)
C13—O1—C17	116.50 (17)	N1—C8—H8A	109.7
C12—O2—H2	109.5	C9—C8—H8A	109.7
C4—N1—C8	126.44 (10)	N1—C8—H8B	109.7
C4—N1—H1	116.8	C9—C8—H8B	109.7
C8—N1—H1	116.7	H8A—C8—H8B	108.2
C10—N2—C9	119.45 (11)	N2—C9—C8	110.36 (10)
S1—C1—H1A	109.5	N2—C9—H9A	109.6
S1—C1—H1B	109.5	C8—C9—H9A	109.6
H1A—C1—H1B	109.5	N2—C9—H9B	109.6
S1—C1—H1C	109.5	C8—C9—H9B	109.6
H1A—C1—H1C	109.5	H9A—C9—H9B	108.1
H1B—C1—H1C	109.5	N2—C10—C11	122.07 (11)
C3—C2—S2	126.69 (9)	N2—C10—H10	119.0
C3—C2—S1	112.17 (8)	C11—C10—H10	119.0
S2—C2—S1	121.14 (7)	C12—C11—C16	119.61 (14)
C2—C3—C4	126.43 (10)	C12—C11—C10	120.49 (11)
C2—C3—C7	124.42 (10)	C16—C11—C10	119.90 (13)
C4—C3—C7	109.03 (10)	O2—C12—C11	122.13 (12)
N1—C4—C3	126.24 (10)	O2—C12—C13	118.47 (12)
N1—C4—C5	122.93 (10)	C11—C12—C13	119.40 (12)
C3—C4—C5	110.81 (10)	O1—C13—C14	125.93 (15)
C4—C5—C6	103.91 (10)	O1—C13—C12	114.69 (14)
C4—C5—H5A	111.0	C14—C13—C12	119.38 (15)
C6—C5—H5A	111.0	C15—C14—C13	121.06 (16)
C4—C5—H5B	111.0	C15—C14—H14	119.5
C6—C5—H5B	111.0	C13—C14—H14	119.5
H5A—C5—H5B	109.0	C16—C15—C14	120.29 (15)
C5—C6—C7	105.86 (10)	C16—C15—H15	119.9
C5—C6—H6A	110.6	C14—C15—H15	119.9
C7—C6—H6A	110.6	C15—C16—C11	120.26 (16)
C5—C6—H6B	110.6	C15—C16—H16	119.9
C7—C6—H6B	110.6	C11—C16—H16	119.9
H6A—C6—H6B	108.7	O1—C17—H17A	109.5
C3—C7—C6	104.22 (10)	O1—C17—H17B	109.5
C3—C7—H7A	110.9	H17A—C17—H17B	109.5
C6—C7—H7A	110.9	O1—C17—H17C	109.5
C3—C7—H7B	110.9	H17A—C17—H17C	109.5
C6—C7—H7B	110.9	H17B—C17—H17C	109.5
H7A—C7—H7B	108.9

C1—S1—C2—C3	−178.88 (11)	N1—C8—C9—N2	−64.63 (13)
C1—S1—C2—S2	1.58 (11)	C9—N2—C10—C11	−178.80 (11)
S2—C2—C3—C4	3.59 (17)	N2—C10—C11—C12	−1.23 (19)
S1—C2—C3—C4	−175.92 (9)	N2—C10—C11—C16	179.42 (12)
S2—C2—C3—C7	179.08 (10)	C16—C11—C12—O2	178.90 (13)
S1—C2—C3—C7	−0.43 (15)	C10—C11—C12—O2	−0.45 (18)
C8—N1—C4—C3	175.70 (11)	C16—C11—C12—C13	−0.74 (19)
C8—N1—C4—C5	−2.59 (19)	C10—C11—C12—C13	179.91 (12)
C2—C3—C4—N1	−2.38 (19)	C17—O1—C13—C14	2.1 (3)
C7—C3—C4—N1	−178.45 (11)	C17—O1—C13—C12	−177.20 (19)
C2—C3—C4—C5	176.08 (11)	O2—C12—C13—O1	−0.1 (2)
C7—C3—C4—C5	0.01 (13)	C11—C12—C13—O1	179.54 (13)
N1—C4—C5—C6	−166.44 (12)	O2—C12—C13—C14	−179.49 (14)
C3—C4—C5—C6	15.04 (14)	C11—C12—C13—C14	0.2 (2)
C4—C5—C6—C7	−23.83 (16)	O1—C13—C14—C15	−178.55 (18)
C2—C3—C7—C6	168.79 (12)	C12—C13—C14—C15	0.7 (3)
C4—C3—C7—C6	−15.05 (15)	C13—C14—C15—C16	−1.1 (3)
C5—C6—C7—C3	23.93 (16)	C14—C15—C16—C11	0.5 (3)
C4—N1—C8—C9	−140.36 (12)	C12—C11—C16—C15	0.4 (2)
C10—N2—C9—C8	111.43 (12)	C10—C11—C16—C15	179.77 (15)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.86	2.32	3.0275 (11)	140
O2—H2···N2	0.82	1.85	2.5806 (14)	147
C9—H9B···O2ⁱ	0.97	2.51	3.1166 (16)	120
C1—H1C···Cgⁱⁱ	0.96	2.95	3.617 (2)	128

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₂N₂O₂S₂
M_r	350.49
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.7933 (2), 10.3486 (2), 11.9532 (3)
α, β, γ (°)	108.038 (1), 93.349 (1), 100.296 (1)
V (Å³)	895.19 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.56 × 0.45 × 0.34

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.678, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	34525, 4761, 4235
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.684

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.109, 1.05
No. of reflections	4761
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.86	2.32	3.0275 (11)	140
O2—H2···N2	0.82	1.85	2.5806 (14)	147
C9—H9B···O2ⁱ	0.97	2.51	3.1166 (16)	120
C1—H1C···Cgⁱⁱ	0.96	2.95	3.617 (2)	128

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

References

Asadi, M., Mohammadi, K., Esmaielzadeh, S., Etemadi, B. & Fun, H. K. (2009). Polyhedron, 28, pp. 1409–1418. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Di Bella, S. & Fragala, I. (2002). New J. Chem. 26, 285–290. Web of Science CrossRef CAS Google Scholar
Güngör, Ö. & Gürkan, P. (2010). Spectrochim. Acta Part A, 77, 304–311. Google Scholar
Kumar, S. B., Bhattacharyya, S., Dutta, S. K. & Tlekink, E. R. T. (1995). J. Chem. Soc. Dalton Trans. pp. 2619–2626. CSD CrossRef Web of Science Google Scholar
Lecren, L., Wernsdorfer, W., Li, Y.-T., Vindigni, A., Miyasaka, H. & Clerac, R. (2007). J. Am. Chem. Soc. 129, 5045–5051. Web of Science CSD CrossRef PubMed CAS Google Scholar
Pereira, E., Gomes, L. R., Low, J. N. & de Castro, B. (2008). Polyhedron, 27, 335–343. Web of Science CSD CrossRef CAS Google Scholar
Sabater, M. J., Alvaro, M., Garcia, H., Palomares, E. & Sherrington, J. C. (1999). Chem. Soc. Rev. 28, 85–102. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o535

doi:10.1107/S1600536811002972

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

Methyl 2-{2-[(E)-(2-hy­dr­oxy-3-meth­­oxy­benzyl­­idene)amino]­ethyl­amino}­cyclo­pentene-1-carbodi­thio­ate

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organic compounds

Methyl 2-{2-[(E)-(2-hydroxy-3-methoxybenzylidene)amino]ethylamino}cyclopentene-1-carbodithioate