Methyl 2-{2-[(E)-(2-hy-droxy-3-meth-oxy-benzyl-idene)amino]-ethyl-amino}-cyclo-pentene-1-carbodithio-ate.

In the title Schiff base compound, C(17)H(22)N(2)O(2)S(2), 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 mol-ecule there are intra-molecular 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 inter-molecular C-H⋯O and C-H⋯π inter-actions 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 = 350.49

Triclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.109

S = 1.05

4761 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAIn class="Chemical">NT; 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 datablocks global, I. DOI: 10.1107/S1600536811002972/su2251sup1.cif

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

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

C17H22N2O2S2	Z = 2
Mr = 350.49	F(000) = 372
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0602P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
4761 reflections	(Δ/σ)max = 0.002
211 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .