Dimethyl 2-(1-benzyl-2-oxoindolin-3-yl­idene)-1,3-dithiole-4,5-dicarboxyl­ate

Bazgir, A.

doi:10.1107/S1600536811002613

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o482

doi:10.1107/S1600536811002613

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Dimethyl 2-(1-benzyl-2-oxoindolin-3-ylidene)-1,3-dithiole-4,5-dicarboxylate

Ayoob Bazgir ^a ^*

^aDepartment of Chemistry, Islamic Azad University, Dooroud Branch, Dooroud 688173551, Iran
^*Correspondence e-mail: a_bazgir@yahoo.com

(Received 16 January 2011; accepted 19 January 2011; online 22 January 2011)

In the title compound, C₂₂H₁₇NO₅S₂, 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. Intermolecular 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_r = 439.51
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.113
S = 1.07
5379 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −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 ).

Supporting information

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

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

checkCIF report

Comment top

Derivatives of sulfur heterocycles such as thiophene and 1,3-dithiole have been widely explored because of their superconducting and optical and electronic switching properties (Marcos et al., 1997). 1,3-Dithiol-2-ylidenes have attracted much attention as building blocks for electronic materials due to their highly electron-donating properties (Segura et al., 2001). In the title compound, the bond distances and angles are within normal ranges. The dihedral angles between the rings A (C8—C15/N1), B (C16/C17/C20/S1/S2) and C (C1—C6) are: A/B = 2.71 (6)°, A/C = 73.65 (5)° and B/C = 75.57 (6)°. Two molecules (symmetry operator: 1-x, y, 0.5-z) are connected by π–π interactions between adjacent A and B rings with a centroid···centroid distance of 3.727Å).

Related literature top

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 et al. (2001).

Experimental top

To a magnetically stirred solution of carbon disulfide (1 mmol) and tributylphosphine (1 mmol) in CH₂Cl₂ (5 ml) were added benzyl isatin (1 mmol) and dimethyl acetyenedicarboxylate (1 mmol) at room temperature. The mixture was stirred for 2.5 h. After completion of the reaction (TLC), the reaction mixture was filtered off and the residue was washed with ether (10 ml) to afford the pure product as a yellow powder (yield 90%, 0.395 g), mp 451–453 K.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Dimethyl 2-(1-benzyl-2-oxoindolin-3-ylidene)-1,3-dithiole-4,5-dicarboxylate top

Crystal data top

C₂₂H₁₇NO₅S₂	F(000) = 1824
M_r = 439.51	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	5379 independent reflections
Graphite monochromator	4206 reflections with I > 2σ(I)
Detector resolution: 0.15 mm pixels mm^-1	R_int = 0.043
ϕ and ω scans	θ_max = 29.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −39→39
T_min = 0.869, T_max = 0.900	k = −12→12
14881 measured reflections	l = −15→20

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) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0447P)² + 2.5812P] where P = (F_o² + 2F_c²)/3
5379 reflections	(Δ/σ)_max = 0.007
271 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₂H₁₇NO₅S₂	V = 3996.6 (5) Å³
M_r = 439.51	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.923 (2) Å	µ = 0.30 mm⁻¹
b = 9.3615 (5) Å	T = 298 K
c = 15.0531 (12) Å	0.49 × 0.4 × 0.35 mm
β = 101.319 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5379 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	4206 reflections with I > 2σ(I)
T_min = 0.869, T_max = 0.900	R_int = 0.043
14881 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.07	Δρ_max = 0.28 e Å⁻³
5379 reflections	Δρ_min = −0.20 e Å⁻³
271 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇NO₅S₂
M_r	439.51
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	28.923 (2), 9.3615 (5), 15.0531 (12)
β (°)	101.319 (6)
V (Å³)	3996.6 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.49 × 0.4 × 0.35

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.869, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	14881, 5379, 4206
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.113, 1.07
No. of reflections	5379
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.20

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

The author is grateful to the Islamic Azad University, Doroud Branch, for financial support.

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Marcos, C. F., Polo, C., Rakitin, O. A., Rees, C. W. & Torroba, T. (1997). Chem. Commun. pp. 879–880. CrossRef Web of Science Google Scholar
Segura, J. L. & Martin, N. (2001). Angew. Chem. Int. Ed. 40, 1372–1409. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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