n-Butyl 2-(2,4-dichloro­anilino)-4,4-dimethyl-6-oxocyclo­hex-1-enecarbo­dithio­ate

El Ashry, E.S.H.; Amer, M.R.; Raza Shah, M.; Ng, S.W.

doi:10.1107/S1600536809036320

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2459

doi:10.1107/S1600536809036320

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n-Butyl 2-(2,4-dichloroanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate

El Sayed H. El Ashry,^a Mohammed R. Amer,^a Muhammad Raza Shah ^a and Seik Weng Ng ^b ^*

^aH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 September 2009; accepted 8 September 2009; online 12 September 2009)

The cyclohexene ring in the title compound, C₁₉H₂₃Cl₂NOS₂, adopts an envelope conformation, with the C atom bearing the two methyl groups representing the flap. This atom deviates by 0.630 (2) Å from the plane passing through the other five atoms of the ring (r.m.s. deviation = 0.020 Å). The molecular conformation is stabilized by an intramolecular N—H⋯S hydrogen bond.

Related literature

For the crystal structures of the n-undecanyl and 2-hydroxyethyl analogues, see: El Ashry et al. (2009a ,b ).

Experimental

Crystal data

C₁₉H₂₃Cl₂NOS₂
M_r = 416.40
Monoclinic, P 2₁ /c
a = 9.0321 (1) Å
b = 19.4422 (2) Å
c = 11.4700 (1) Å
β = 100.331 (1)°
V = 1981.52 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.55 mm⁻¹
T = 123 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.853, T_max = 0.947
18747 measured reflections
4554 independent reflections
4279 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.070
S = 1.00
4554 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2	0.91 (2)	2.08 (2)	2.885 (1)	147 (2)

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036320/ci2904sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036320/ci2904Isup2.hkl

checkCIF report

Related literature top

For the crystal structures of the n-undecanyl and 2-hydroxyethyl analogues, see: El Ashry et al. (2009a,b).

Experimental top

A cooled (283 K) solution of (2,4-dichloroanilino)-4,4-dimethyl-6-oxocyclohex-1-ene (0.2 mol) and sodium hydroxide (0.2 mol) in DMSO (30 ml) and water (2 ml), was treated with carbon disulfide (0.3 mol). After 40 min, n-bromobutane (0.15 mol) was added and the reaction mixture was left overnight. The mixture was then diluted with water (200 ml) and acidified with 10% hydrochloric acid. The product was purified on silica gel column chromatography to give yellow crystals when recrystallized from ethanol (m.p. 401 K).

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) plot of C₁₉H₂₃Cl₂NOS₂ at the 70% probability level; H atoms are drawn as spheres of arbitrary radius.

n-Butyl 2-(2,4-dichloroanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate top

Crystal data top

C₁₉H₂₃Cl₂NOS₂	F(000) = 872
M_r = 416.40	D_x = 1.396 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9957 reflections
a = 9.0321 (1) Å	θ = 2.5–28.2°
b = 19.4422 (2) Å	µ = 0.55 mm⁻¹
c = 11.4700 (1) Å	T = 123 K
β = 100.331 (1)°	Block, yellow
V = 1981.52 (3) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4554 independent reflections
Radiation source: fine-focus sealed tube	4279 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.853, T_max = 0.947	k = −25→25
18747 measured reflections	l = −14→14

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0405P)² + 0.9836P] where P = (F_o² + 2F_c²)/3
4554 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₂₃Cl₂NOS₂	V = 1981.52 (3) Å³
M_r = 416.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0321 (1) Å	µ = 0.55 mm⁻¹
b = 19.4422 (2) Å	T = 123 K
c = 11.4700 (1) Å	0.30 × 0.20 × 0.10 mm
β = 100.331 (1)°

Data collection top

Bruker SMART APEX diffractometer	4554 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4279 reflections with I > 2σ(I)
T_min = 0.853, T_max = 0.947	R_int = 0.016
18747 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.41 e Å⁻³
4554 reflections	Δρ_min = −0.25 e Å⁻³
230 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
Cl1	0.66246 (3)	0.420713 (17)	0.99199 (3)	0.02548 (8)
Cl2	1.25630 (3)	0.391875 (17)	1.00782 (3)	0.02572 (8)
S1	0.17044 (3)	0.547076 (14)	0.56447 (2)	0.01521 (7)
S2	0.45310 (3)	0.595199 (14)	0.71292 (3)	0.01818 (8)
O1	0.18119 (12)	0.41970 (5)	0.52118 (12)	0.0435 (3)
N1	0.65717 (11)	0.47990 (5)	0.74995 (8)	0.01551 (19)
H1	0.625 (2)	0.5237 (10)	0.7584 (16)	0.033 (4)*
C1	0.31311 (14)	0.40793 (6)	0.56335 (11)	0.0194 (2)
C2	0.37252 (13)	0.33742 (6)	0.54278 (10)	0.0176 (2)
H2A	0.4118	0.3381	0.4676	0.021*
H2B	0.2878	0.3044	0.5331	0.021*
C3	0.49613 (12)	0.31158 (6)	0.64090 (10)	0.0150 (2)
C4	0.61567 (12)	0.36787 (6)	0.66192 (10)	0.0163 (2)
H4A	0.6925	0.3547	0.7312	0.020*
H4B	0.6662	0.3698	0.5922	0.020*
C5	0.55899 (12)	0.43880 (6)	0.68327 (9)	0.0133 (2)
C6	0.41136 (12)	0.46044 (6)	0.63000 (10)	0.0141 (2)
C7	0.56586 (14)	0.24599 (6)	0.60044 (11)	0.0203 (2)
H7A	0.6051	0.2554	0.5277	0.030*
H7B	0.4890	0.2100	0.5851	0.030*
H7C	0.6482	0.2306	0.6626	0.030*
C8	0.43521 (15)	0.29707 (7)	0.75460 (11)	0.0246 (3)
H8A	0.3590	0.2607	0.7397	0.037*
H8B	0.3898	0.3390	0.7800	0.037*
H8C	0.5178	0.2822	0.8170	0.037*
C9	0.80208 (12)	0.45912 (6)	0.81146 (10)	0.0144 (2)
C10	0.81793 (13)	0.43077 (6)	0.92496 (10)	0.0160 (2)
C11	0.95775 (13)	0.40992 (6)	0.98561 (10)	0.0171 (2)
H11	0.9681	0.3902	1.0624	0.021*
C12	1.08177 (13)	0.41848 (6)	0.93158 (10)	0.0171 (2)
C13	1.07029 (13)	0.44805 (6)	0.82040 (10)	0.0187 (2)
H13	1.1572	0.4543	0.7856	0.022*
C14	0.92928 (13)	0.46846 (6)	0.76063 (10)	0.0169 (2)
H14	0.9198	0.4889	0.6845	0.020*
C15	0.35496 (12)	0.53004 (6)	0.63903 (9)	0.0140 (2)
C16	0.14330 (13)	0.63819 (6)	0.58501 (10)	0.0162 (2)
H16A	0.2411	0.6618	0.5885	0.019*
H16B	0.0737	0.6561	0.5150	0.019*
C17	0.08095 (13)	0.65650 (6)	0.69585 (10)	0.0169 (2)
H17A	0.1575	0.6462	0.7669	0.020*
H17B	−0.0089	0.6280	0.6994	0.020*
C18	0.03800 (14)	0.73269 (6)	0.69634 (11)	0.0226 (2)
H18A	0.1254	0.7609	0.6846	0.027*
H18B	−0.0451	0.7418	0.6292	0.027*
C19	−0.01100 (17)	0.75431 (7)	0.81137 (13)	0.0308 (3)
H19A	−0.0374	0.8033	0.8074	0.046*
H19B	0.0716	0.7464	0.8780	0.046*
H19C	−0.0988	0.7272	0.8227	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01664 (14)	0.03539 (18)	0.02576 (15)	−0.00287 (11)	0.00749 (11)	0.00779 (12)
Cl2	0.01535 (14)	0.03229 (17)	0.02687 (16)	0.00715 (11)	−0.00338 (11)	0.00089 (12)
S1	0.01301 (13)	0.01582 (14)	0.01536 (13)	0.00136 (9)	−0.00128 (10)	−0.00127 (9)
S2	0.01510 (14)	0.01493 (14)	0.02250 (15)	−0.00004 (10)	−0.00210 (11)	−0.00381 (10)
O1	0.0189 (5)	0.0256 (5)	0.0756 (8)	0.0054 (4)	−0.0192 (5)	−0.0213 (5)
N1	0.0130 (4)	0.0142 (5)	0.0177 (5)	−0.0003 (3)	−0.0015 (3)	−0.0014 (4)
C1	0.0162 (5)	0.0169 (5)	0.0229 (6)	0.0000 (4)	−0.0023 (4)	−0.0034 (4)
C2	0.0170 (5)	0.0148 (5)	0.0188 (5)	−0.0003 (4)	−0.0028 (4)	−0.0027 (4)
C3	0.0135 (5)	0.0141 (5)	0.0162 (5)	−0.0014 (4)	0.0000 (4)	0.0001 (4)
C4	0.0123 (5)	0.0148 (5)	0.0210 (5)	−0.0003 (4)	0.0012 (4)	−0.0022 (4)
C5	0.0128 (5)	0.0150 (5)	0.0125 (5)	−0.0017 (4)	0.0028 (4)	0.0006 (4)
C6	0.0122 (5)	0.0145 (5)	0.0150 (5)	−0.0011 (4)	0.0008 (4)	−0.0008 (4)
C7	0.0188 (5)	0.0145 (5)	0.0259 (6)	−0.0003 (4)	−0.0010 (4)	−0.0021 (4)
C8	0.0264 (6)	0.0257 (6)	0.0225 (6)	−0.0027 (5)	0.0066 (5)	0.0050 (5)
C9	0.0124 (5)	0.0139 (5)	0.0156 (5)	−0.0009 (4)	−0.0009 (4)	−0.0023 (4)
C10	0.0138 (5)	0.0169 (5)	0.0175 (5)	−0.0024 (4)	0.0035 (4)	−0.0003 (4)
C11	0.0181 (6)	0.0169 (5)	0.0153 (5)	−0.0003 (4)	0.0002 (4)	0.0009 (4)
C12	0.0128 (5)	0.0178 (5)	0.0186 (5)	0.0025 (4)	−0.0028 (4)	−0.0027 (4)
C13	0.0142 (5)	0.0239 (6)	0.0183 (5)	−0.0002 (4)	0.0037 (4)	−0.0027 (4)
C14	0.0169 (5)	0.0197 (5)	0.0137 (5)	−0.0016 (4)	0.0010 (4)	−0.0012 (4)
C15	0.0126 (5)	0.0166 (5)	0.0125 (5)	−0.0006 (4)	0.0013 (4)	0.0003 (4)
C16	0.0176 (5)	0.0144 (5)	0.0158 (5)	0.0018 (4)	0.0007 (4)	0.0019 (4)
C17	0.0156 (5)	0.0163 (5)	0.0184 (5)	0.0011 (4)	0.0020 (4)	−0.0009 (4)
C18	0.0224 (6)	0.0180 (6)	0.0251 (6)	0.0033 (4)	−0.0016 (5)	−0.0030 (4)
C19	0.0309 (7)	0.0264 (7)	0.0340 (7)	0.0087 (5)	0.0030 (6)	−0.0091 (6)

Geometric parameters (Å, º) top

Cl1—C10	1.7287 (11)	C8—H8A	0.98
Cl2—C12	1.7387 (12)	C8—H8B	0.98
S1—C15	1.7628 (11)	C8—H8C	0.98
S1—C16	1.8094 (12)	C9—C14	1.3903 (16)
S2—C15	1.6851 (11)	C9—C10	1.3973 (16)
O1—C1	1.2244 (16)	C10—C11	1.3885 (16)
N1—C5	1.3291 (14)	C11—C12	1.3840 (17)
N1—C9	1.4293 (14)	C11—H11	0.95
N1—H1	0.911 (18)	C12—C13	1.3856 (17)
C1—C6	1.4733 (15)	C13—C14	1.3916 (16)
C1—C2	1.5061 (16)	C13—H13	0.95
C2—C3	1.5214 (15)	C14—H14	0.95
C2—H2A	0.99	C16—C17	1.5222 (16)
C2—H2B	0.99	C16—H16A	0.99
C3—C4	1.5258 (15)	C16—H16B	0.99
C3—C8	1.5300 (16)	C17—C18	1.5315 (16)
C3—C7	1.5307 (16)	C17—H17A	0.99
C4—C5	1.5063 (15)	C17—H17B	0.99
C4—H4A	0.99	C18—C19	1.5240 (19)
C4—H4B	0.99	C18—H18A	0.99
C5—C6	1.4269 (15)	C18—H18B	0.99
C6—C15	1.4562 (15)	C19—H19A	0.98
C7—H7A	0.98	C19—H19B	0.98
C7—H7B	0.98	C19—H19C	0.98
C7—H7C	0.98

C15—S1—C16	105.02 (5)	C14—C9—N1	120.57 (10)
C5—N1—C9	124.86 (10)	C10—C9—N1	120.21 (10)
C5—N1—H1	115.5 (11)	C11—C10—C9	120.93 (10)
C9—N1—H1	119.6 (11)	C11—C10—Cl1	118.85 (9)
O1—C1—C6	121.90 (11)	C9—C10—Cl1	120.22 (9)
O1—C1—C2	117.19 (11)	C12—C11—C10	118.49 (10)
C6—C1—C2	120.90 (10)	C12—C11—H11	120.8
C1—C2—C3	114.80 (9)	C10—C11—H11	120.8
C1—C2—H2A	108.6	C11—C12—C13	121.94 (11)
C3—C2—H2A	108.6	C11—C12—Cl2	118.20 (9)
C1—C2—H2B	108.6	C13—C12—Cl2	119.85 (9)
C3—C2—H2B	108.6	C12—C13—C14	118.85 (11)
H2A—C2—H2B	107.5	C12—C13—H13	120.6
C2—C3—C4	106.54 (9)	C14—C13—H13	120.6
C2—C3—C8	111.29 (10)	C9—C14—C13	120.55 (11)
C4—C3—C8	110.49 (10)	C9—C14—H14	119.7
C2—C3—C7	109.76 (9)	C13—C14—H14	119.7
C4—C3—C7	109.11 (9)	C6—C15—S2	125.12 (8)
C8—C3—C7	109.58 (10)	C6—C15—S1	116.90 (8)
C5—C4—C3	115.52 (9)	S2—C15—S1	117.97 (6)
C5—C4—H4A	108.4	C17—C16—S1	114.63 (8)
C3—C4—H4A	108.4	C17—C16—H16A	108.6
C5—C4—H4B	108.4	S1—C16—H16A	108.6
C3—C4—H4B	108.4	C17—C16—H16B	108.6
H4A—C4—H4B	107.5	S1—C16—H16B	108.6
N1—C5—C6	123.03 (10)	H16A—C16—H16B	107.6
N1—C5—C4	115.65 (10)	C16—C17—C18	111.18 (10)
C6—C5—C4	121.26 (10)	C16—C17—H17A	109.4
C5—C6—C15	123.74 (10)	C18—C17—H17A	109.4
C5—C6—C1	116.59 (10)	C16—C17—H17B	109.4
C15—C6—C1	119.67 (10)	C18—C17—H17B	109.4
C3—C7—H7A	109.5	H17A—C17—H17B	108.0
C3—C7—H7B	109.5	C19—C18—C17	112.52 (11)
H7A—C7—H7B	109.5	C19—C18—H18A	109.1
C3—C7—H7C	109.5	C17—C18—H18A	109.1
H7A—C7—H7C	109.5	C19—C18—H18B	109.1
H7B—C7—H7C	109.5	C17—C18—H18B	109.1
C3—C8—H8A	109.5	H18A—C18—H18B	107.8
C3—C8—H8B	109.5	C18—C19—H19A	109.5
H8A—C8—H8B	109.5	C18—C19—H19B	109.5
C3—C8—H8C	109.5	H19A—C19—H19B	109.5
H8A—C8—H8C	109.5	C18—C19—H19C	109.5
H8B—C8—H8C	109.5	H19A—C19—H19C	109.5
C14—C9—C10	119.20 (10)	H19B—C19—H19C	109.5

O1—C1—C2—C3	−149.43 (13)	C14—C9—C10—C11	−2.07 (17)
C6—C1—C2—C3	31.47 (16)	N1—C9—C10—C11	179.58 (10)
C1—C2—C3—C4	−52.05 (13)	C14—C9—C10—Cl1	178.25 (9)
C1—C2—C3—C8	68.46 (13)	N1—C9—C10—Cl1	−0.10 (15)
C1—C2—C3—C7	−170.06 (10)	C9—C10—C11—C12	0.65 (17)
C2—C3—C4—C5	52.18 (12)	Cl1—C10—C11—C12	−179.66 (9)
C8—C3—C4—C5	−68.83 (13)	C10—C11—C12—C13	1.04 (17)
C7—C3—C4—C5	170.62 (9)	C10—C11—C12—Cl2	−179.71 (9)
C9—N1—C5—C6	175.52 (10)	C11—C12—C13—C14	−1.26 (18)
C9—N1—C5—C4	−7.29 (16)	Cl2—C12—C13—C14	179.50 (9)
C3—C4—C5—N1	151.63 (10)	C10—C9—C14—C13	1.84 (17)
C3—C4—C5—C6	−31.13 (15)	N1—C9—C14—C13	−179.82 (10)
N1—C5—C6—C15	2.50 (17)	C12—C13—C14—C9	−0.21 (17)
C4—C5—C6—C15	−174.53 (10)	C5—C6—C15—S2	−0.17 (16)
N1—C5—C6—C1	−177.12 (10)	C1—C6—C15—S2	179.44 (9)
C4—C5—C6—C1	5.84 (15)	C5—C6—C15—S1	178.79 (8)
O1—C1—C6—C5	174.85 (13)	C1—C6—C15—S1	−1.60 (14)
C2—C1—C6—C5	−6.09 (16)	C16—S1—C15—C6	−175.86 (8)
O1—C1—C6—C15	−4.79 (19)	C16—S1—C15—S2	3.18 (8)
C2—C1—C6—C15	174.27 (10)	C15—S1—C16—C17	−89.34 (9)
C5—N1—C9—C14	95.10 (14)	S1—C16—C17—C18	−170.96 (8)
C5—N1—C9—C10	−86.58 (14)	C16—C17—C18—C19	−174.62 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.91 (2)	2.08 (2)	2.885 (1)	147 (2)

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃Cl₂NOS₂
M_r	416.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	9.0321 (1), 19.4422 (2), 11.4700 (1)
β (°)	100.331 (1)
V (Å³)	1981.52 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.853, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	18747, 4554, 4279
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.070, 1.00
No. of reflections	4554
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.25

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.91 (2)	2.08 (2)	2.885 (1)	147 (2)

Acknowledgements

The authors thank the University of Karachi and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
El Ashry, E. S. H., Amer, M. R., Shah, M. R. & Ng, S. W. (2009a). Acta Cryst. E65, o601. Web of Science CSD CrossRef IUCr Journals Google Scholar
El Ashry, E. S. H., Amer, M. R., Shah, M. R. & Ng, S. W. (2009b). Acta Cryst. E65, o602. Web of Science CSD CrossRef IUCr Journals 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
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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Volume 65| Part 10| October 2009| Page o2459

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n-Butyl 2-(2,4-di­chloro­anilino)-4,4-di­methyl-6-oxo­cyclo­hex-1-enecarbo­di­thio­ate

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n-Butyl 2-(2,4-dichloroanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate