Dimethyl 2-(1-benzyl-2-oxoindolin-3-yl-idene)-1,3-dithiole-4,5-dicarboxyl-ate.

In the title compound, C(22)H(17)NO(5)S(2), the dithiole and oxindole rings are almost coplanar [dihedral angle = 2.71 (8)°] and the phenyl ring makes a dihedral angle of 73.65 (5)° with the oxindole ring. Inter-molecular π-π contacts between adjacent oxindole and dithiole rings [centroid-centroid distance = 3.7273 (11) Å] stabilize the crystal packing.

Related literature

For the superconducting and optical and electronic switching properties of derivatives of sulfur heterocycles such as thio­phene and 1,3-dithiole, see: Marcos et al. (1997 ▶). For the use of 1,3-dithiol-2-ylidenes as building blocks for electronic materials due to their highly electron-donating properties, see: Segura & Martin (2001 ▶).

Experimental

Crystal data

C22H17NO5S2

M = 439.51

Monoclinic,

a = 28.923 (2) Å

b = 9.3615 (5) Å

c = 15.0531 (12) Å

β = 101.319 (6)°

V = 3996.6 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 298 K

0.49 × 0.4 × 0.35 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.869, T max = 0.900

14881 measured reflections

5379 independent reflections

4206 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.113

S = 1.07

5379 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002613/bt5465sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002613/bt5465Isup2.hkl

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

C22H17NO5S2	F(000) = 1824
Mr = 439.51	Dx = 1.461 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 14881 reflections
a = 28.923 (2) Å	θ = 2.3–29.3°
b = 9.3615 (5) Å	µ = 0.30 mm−1
c = 15.0531 (12) Å	T = 298 K
β = 101.319 (6)°	Block, yellow
V = 3996.6 (5) Å3	0.49 × 0.4 × 0.35 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	5379 independent reflections
graphite	4206 reflections with I > 2σ(I)
Detector resolution: 0.15 mm pixels mm-1	Rint = 0.043
φ and ω scans	θmax = 29.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −39→39
Tmin = 0.869, Tmax = 0.900	k = −12→12
14881 measured reflections	l = −15→20

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) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0447P)2 + 2.5812P] where P = (Fo2 + 2Fc2)/3
5379 reflections	(Δ/σ)max = 0.007
271 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.20 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
C1	0.69401 (6)	0.1560 (2)	0.15830 (13)	0.0440 (4)
H1	0.6678	0.097	0.1428	0.053*
C2	0.72780 (7)	0.1575 (2)	0.10498 (15)	0.0517 (5)
H2	0.7243	0.0992	0.0541	0.062*
C3	0.76654 (7)	0.2450 (3)	0.12692 (16)	0.0553 (5)
H3	0.7892	0.2459	0.0909	0.066*
C4	0.77168 (7)	0.3309 (2)	0.20198 (18)	0.0574 (6)
H4	0.7978	0.3906	0.2165	0.069*
C5	0.73822 (7)	0.3290 (2)	0.25619 (16)	0.0505 (5)
H5	0.7422	0.3866	0.3075	0.061*
C6	0.69882 (6)	0.24178 (19)	0.23467 (12)	0.0387 (4)
C7	0.66189 (6)	0.2389 (2)	0.29233 (13)	0.0463 (4)
H7A	0.6588	0.142	0.3132	0.056*
H7B	0.6722	0.2985	0.3452	0.056*
C8	0.60243 (6)	0.4311 (2)	0.22905 (13)	0.0405 (4)
C9	0.62848 (7)	0.5531 (2)	0.25334 (15)	0.0512 (5)
H9	0.6597	0.548	0.2835	0.061*
C10	0.60660 (8)	0.6838 (2)	0.23143 (17)	0.0575 (5)
H10	0.6235	0.7675	0.2473	0.069*
C11	0.56030 (8)	0.6924 (2)	0.18661 (17)	0.0579 (6)
H11	0.5464	0.7813	0.173	0.069*
C12	0.53431 (7)	0.5688 (2)	0.16160 (15)	0.0495 (5)
H12	0.5031	0.5747	0.1311	0.059*
C13	0.55522 (6)	0.43703 (19)	0.18238 (13)	0.0400 (4)
C14	0.53962 (6)	0.28985 (19)	0.16840 (13)	0.0394 (4)
C15	0.57937 (6)	0.1980 (2)	0.20878 (13)	0.0413 (4)
C16	0.49754 (6)	0.23430 (18)	0.12636 (12)	0.0371 (4)
C17	0.41162 (6)	0.19850 (18)	0.04219 (13)	0.0383 (4)
C18	0.36382 (7)	0.2325 (2)	−0.01156 (13)	0.0432 (4)
C19	0.30976 (8)	0.4193 (3)	−0.0566 (2)	0.0695 (7)
H19A	0.285	0.3699	−0.0351	0.083*
H19B	0.3077	0.3992	−0.1198	0.083*
H19C	0.3066	0.5202	−0.0482	0.083*
C20	0.42817 (6)	0.06699 (18)	0.06540 (13)	0.0375 (4)
C21	0.40009 (6)	−0.06847 (18)	0.05586 (13)	0.0396 (4)
C22	0.40263 (9)	−0.3108 (2)	0.01813 (17)	0.0588 (6)
H22A	0.3728	−0.3055	−0.0232	0.071*
H22B	0.3978	−0.3414	0.0765	0.071*
H22C	0.4227	−0.3779	−0.0043	0.071*
S1	0.450578 (16)	0.33875 (5)	0.07467 (4)	0.04225 (12)
S2	0.486715 (15)	0.05076 (5)	0.12000 (4)	0.04242 (12)
O1	0.58087 (5)	0.06729 (15)	0.21051 (11)	0.0533 (4)
O2	0.33748 (6)	0.14837 (16)	−0.05296 (13)	0.0725 (5)
O3	0.35496 (5)	0.37174 (14)	−0.00634 (11)	0.0525 (4)
O4	0.36255 (5)	−0.08135 (16)	0.07518 (12)	0.0573 (4)
O5	0.42460 (5)	−0.17201 (14)	0.02619 (11)	0.0524 (4)
N1	0.61588 (5)	0.28852 (17)	0.24442 (12)	0.0434 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0381 (9)	0.0446 (9)	0.0469 (10)	−0.0022 (7)	0.0021 (8)	0.0000 (8)
C2	0.0504 (11)	0.0573 (12)	0.0468 (11)	0.0068 (9)	0.0084 (9)	−0.0006 (9)
C3	0.0413 (10)	0.0644 (13)	0.0628 (13)	0.0087 (9)	0.0166 (9)	0.0166 (11)
C4	0.0320 (9)	0.0552 (12)	0.0831 (16)	−0.0061 (8)	0.0068 (9)	0.0046 (11)
C5	0.0383 (9)	0.0501 (11)	0.0589 (12)	−0.0047 (8)	−0.0011 (8)	−0.0086 (9)
C6	0.0309 (7)	0.0408 (9)	0.0418 (9)	0.0015 (7)	0.0007 (7)	0.0032 (7)
C7	0.0383 (9)	0.0576 (11)	0.0415 (10)	−0.0002 (8)	0.0040 (8)	−0.0015 (9)
C8	0.0372 (8)	0.0424 (9)	0.0431 (10)	−0.0050 (7)	0.0105 (7)	−0.0057 (8)
C9	0.0435 (10)	0.0526 (11)	0.0573 (12)	−0.0109 (9)	0.0092 (9)	−0.0128 (10)
C10	0.0586 (12)	0.0452 (11)	0.0689 (15)	−0.0154 (9)	0.0131 (11)	−0.0132 (10)
C11	0.0613 (13)	0.0379 (10)	0.0732 (15)	−0.0043 (9)	0.0100 (11)	−0.0069 (10)
C12	0.0459 (10)	0.0418 (10)	0.0596 (13)	−0.0018 (8)	0.0071 (9)	−0.0027 (9)
C13	0.0365 (8)	0.0414 (9)	0.0433 (10)	−0.0053 (7)	0.0104 (7)	−0.0036 (7)
C14	0.0341 (8)	0.0379 (9)	0.0470 (10)	−0.0029 (7)	0.0095 (7)	−0.0004 (7)
C15	0.0333 (8)	0.0435 (9)	0.0483 (10)	−0.0029 (7)	0.0111 (7)	−0.0009 (8)
C16	0.0342 (8)	0.0344 (8)	0.0433 (9)	−0.0015 (6)	0.0091 (7)	−0.0014 (7)
C17	0.0370 (8)	0.0330 (8)	0.0427 (10)	−0.0013 (6)	0.0026 (7)	−0.0023 (7)
C18	0.0430 (9)	0.0373 (9)	0.0459 (10)	−0.0031 (7)	0.0003 (8)	0.0002 (8)
C19	0.0529 (12)	0.0568 (13)	0.0889 (19)	0.0120 (10)	−0.0108 (12)	0.0065 (13)
C20	0.0364 (8)	0.0334 (8)	0.0423 (9)	−0.0039 (6)	0.0064 (7)	−0.0023 (7)
C21	0.0397 (9)	0.0334 (8)	0.0429 (9)	−0.0042 (7)	0.0011 (7)	0.0008 (7)
C22	0.0763 (15)	0.0299 (9)	0.0697 (15)	−0.0083 (9)	0.0127 (12)	−0.0028 (9)
S1	0.0392 (2)	0.0304 (2)	0.0537 (3)	−0.00321 (17)	0.00062 (19)	0.00031 (19)
S2	0.0350 (2)	0.0320 (2)	0.0588 (3)	−0.00095 (16)	0.00545 (19)	0.00117 (19)
O1	0.0452 (7)	0.0397 (7)	0.0737 (10)	−0.0010 (6)	0.0083 (7)	0.0042 (7)
O2	0.0622 (9)	0.0455 (8)	0.0922 (13)	−0.0049 (7)	−0.0281 (9)	−0.0075 (8)
O3	0.0453 (7)	0.0376 (7)	0.0671 (10)	0.0032 (5)	−0.0078 (7)	−0.0009 (6)
O4	0.0440 (7)	0.0472 (8)	0.0828 (11)	−0.0089 (6)	0.0174 (7)	−0.0041 (7)
O5	0.0579 (8)	0.0310 (6)	0.0709 (10)	−0.0048 (6)	0.0192 (7)	−0.0061 (6)
N1	0.0318 (7)	0.0463 (8)	0.0517 (9)	−0.0019 (6)	0.0068 (6)	−0.0033 (7)

C1—C2	1.381 (3)	C12—H12	0.93
C1—C6	1.387 (3)	C13—C14	1.452 (2)
C1—H1	0.93	C14—C16	1.360 (2)
C2—C3	1.375 (3)	C14—C15	1.469 (3)
C2—H2	0.93	C15—O1	1.224 (2)
C3—C4	1.371 (3)	C15—N1	1.378 (2)
C3—H3	0.93	C16—S1	1.7297 (18)
C4—C5	1.383 (3)	C16—S2	1.7458 (18)
C4—H4	0.93	C17—C20	1.342 (2)
C5—C6	1.387 (2)	C17—C18	1.493 (2)
C5—H5	0.93	C17—S1	1.7368 (17)
C6—C7	1.503 (3)	C18—O2	1.184 (2)
C7—N1	1.460 (2)	C18—O3	1.334 (2)
C7—H7A	0.97	C19—O3	1.446 (2)
C7—H7B	0.97	C19—H19A	0.96
C8—C9	1.377 (3)	C19—H19B	0.96
C8—N1	1.397 (2)	C19—H19C	0.96
C8—C13	1.409 (2)	C20—C21	1.498 (2)
C9—C10	1.387 (3)	C20—S2	1.7376 (18)
C9—H9	0.93	C21—O4	1.184 (2)
C10—C11	1.378 (3)	C21—O5	1.329 (2)
C10—H10	0.93	C22—O5	1.441 (2)
C11—C12	1.391 (3)	C22—H22A	0.96
C11—H11	0.93	C22—H22B	0.96
C12—C13	1.382 (3)	C22—H22C	0.96
C2—C1—C6	120.58 (18)	C8—C13—C14	106.16 (16)
C2—C1—H1	119.7	C16—C14—C13	130.87 (17)
C6—C1—H1	119.7	C16—C14—C15	121.66 (16)
C3—C2—C1	120.2 (2)	C13—C14—C15	107.46 (15)
C3—C2—H2	119.9	O1—C15—N1	125.82 (17)
C1—C2—H2	119.9	O1—C15—C14	128.00 (17)
C4—C3—C2	119.9 (2)	N1—C15—C14	106.17 (15)
C4—C3—H3	120	C14—C16—S1	123.04 (14)
C2—C3—H3	120	C14—C16—S2	122.44 (14)
C3—C4—C5	120.24 (19)	S1—C16—S2	114.52 (10)
C3—C4—H4	119.9	C20—C17—C18	125.59 (16)
C5—C4—H4	119.9	C20—C17—S1	116.20 (13)
C4—C5—C6	120.5 (2)	C18—C17—S1	118.16 (13)
C4—C5—H5	119.7	O2—C18—O3	124.74 (18)
C6—C5—H5	119.7	O2—C18—C17	125.09 (18)
C1—C6—C5	118.57 (18)	O3—C18—C17	110.17 (15)
C1—C6—C7	120.09 (16)	O3—C19—H19A	109.5
C5—C6—C7	121.34 (18)	O3—C19—H19B	109.5
N1—C7—C6	113.04 (16)	H19A—C19—H19B	109.5
N1—C7—H7A	109	O3—C19—H19C	109.5
C6—C7—H7A	109	H19A—C19—H19C	109.5
N1—C7—H7B	109	H19B—C19—H19C	109.5
C6—C7—H7B	109	C17—C20—C21	126.35 (16)
H7A—C7—H7B	107.8	C17—C20—S2	117.91 (13)
C9—C8—N1	128.91 (17)	C21—C20—S2	115.54 (13)
C9—C8—C13	121.75 (18)	O4—C21—O5	125.71 (17)
N1—C8—C13	109.33 (15)	O4—C21—C20	124.68 (17)
C8—C9—C10	117.89 (19)	O5—C21—C20	109.56 (15)
C8—C9—H9	121.1	O5—C22—H22A	109.5
C10—C9—H9	121.1	O5—C22—H22B	109.5
C11—C10—C9	121.45 (19)	H22A—C22—H22B	109.5
C11—C10—H10	119.3	O5—C22—H22C	109.5
C9—C10—H10	119.3	H22A—C22—H22C	109.5
C10—C11—C12	120.4 (2)	H22B—C22—H22C	109.5
C10—C11—H11	119.8	C16—S1—C17	96.21 (8)
C12—C11—H11	119.8	C20—S2—C16	95.02 (8)
C13—C12—C11	119.46 (19)	C18—O3—C19	115.73 (17)
C13—C12—H12	120.3	C21—O5—C22	115.50 (16)
C11—C12—H12	120.3	C15—N1—C8	110.87 (15)
C12—C13—C8	119.08 (17)	C15—N1—C7	123.44 (16)
C12—C13—C14	134.76 (17)	C8—N1—C7	125.68 (16)
C6—C1—C2—C3	−0.4 (3)	S1—C17—C18—O2	164.3 (2)
C1—C2—C3—C4	0.1 (3)	C20—C17—C18—O3	166.85 (19)
C2—C3—C4—C5	0.6 (3)	S1—C17—C18—O3	−15.7 (2)
C3—C4—C5—C6	−0.9 (3)	C18—C17—C20—C21	−10.8 (3)
C2—C1—C6—C5	0.1 (3)	S1—C17—C20—C21	171.74 (15)
C2—C1—C6—C7	−179.80 (18)	C18—C17—C20—S2	174.62 (16)
C4—C5—C6—C1	0.5 (3)	S1—C17—C20—S2	−2.9 (2)
C4—C5—C6—C7	−179.58 (19)	C17—C20—C21—O4	−43.9 (3)
C1—C6—C7—N1	−63.5 (2)	S2—C20—C21—O4	130.81 (19)
C5—C6—C7—N1	116.6 (2)	C17—C20—C21—O5	138.6 (2)
N1—C8—C9—C10	−178.9 (2)	S2—C20—C21—O5	−46.6 (2)
C13—C8—C9—C10	0.8 (3)	C14—C16—S1—C17	−178.17 (17)
C8—C9—C10—C11	−0.1 (3)	S2—C16—S1—C17	2.04 (12)
C9—C10—C11—C12	−0.4 (4)	C20—C17—S1—C16	0.44 (17)
C10—C11—C12—C13	0.3 (4)	C18—C17—S1—C16	−177.23 (15)
C11—C12—C13—C8	0.4 (3)	C17—C20—S2—C16	3.65 (17)
C11—C12—C13—C14	179.3 (2)	C21—C20—S2—C16	−171.53 (14)
C9—C8—C13—C12	−0.9 (3)	C14—C16—S2—C20	177.01 (17)
N1—C8—C13—C12	178.79 (18)	S1—C16—S2—C20	−3.19 (12)
C9—C8—C13—C14	179.82 (18)	O2—C18—O3—C19	−0.7 (3)
N1—C8—C13—C14	−0.4 (2)	C17—C18—O3—C19	179.30 (19)
C12—C13—C14—C16	1.8 (4)	O4—C21—O5—C22	−0.4 (3)
C8—C13—C14—C16	−179.2 (2)	C20—C21—O5—C22	177.06 (17)
C12—C13—C14—C15	−178.9 (2)	O1—C15—N1—C8	178.81 (19)
C8—C13—C14—C15	0.2 (2)	C14—C15—N1—C8	−0.5 (2)
C16—C14—C15—O1	0.3 (3)	O1—C15—N1—C7	−1.8 (3)
C13—C14—C15—O1	−179.1 (2)	C14—C15—N1—C7	178.90 (17)
C16—C14—C15—N1	179.60 (17)	C9—C8—N1—C15	−179.7 (2)
C13—C14—C15—N1	0.2 (2)	C13—C8—N1—C15	0.6 (2)
C13—C14—C16—S1	1.5 (3)	C9—C8—N1—C7	0.9 (3)
C15—C14—C16—S1	−177.74 (14)	C13—C8—N1—C7	−178.76 (18)
C13—C14—C16—S2	−178.71 (16)	C6—C7—N1—C15	101.1 (2)
C15—C14—C16—S2	2.0 (3)	C6—C7—N1—C8	−79.6 (2)
C20—C17—C18—O2	−13.2 (4)