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

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

doi:10.1107/S1600536809006199

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o602

doi:10.1107/S1600536809006199

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

El Sayed H. El Ashry,^a Mohammed R. Amer,^a M. 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 19 February 2009; accepted 19 February 2009; online 25 February 2009)

The six-membered cyclohexene ring in the title compound, C₁₇H₁₉Cl₂NOS₂, adopts an envelope conformation, with the C atom bearing the two methyl groups representing the flap. This atom deviates by 0.716 (3) Å from the plane passing through the other five atoms of the ring (r.m.s. deviation = 0.072 Å). The molecular conformation is stabilized by an intramolecular N—H⋯S hydrogen bond. The hydroxy group engages in intermolecular O—H⋯O hydrogen bonding with adjacent acceptor atoms to generate a zigzag chain running along the c axis.

Related literature

For background, see: El Ashry et al. (2009 ).

Experimental

Crystal data

C₁₇H₁₉Cl₂NO₂S₂
M_r = 404.35
Monoclinic, P 2₁ /c
a = 11.7310 (2) Å
b = 14.0903 (2) Å
c = 12.0416 (2) Å
β = 111.245 (1)°
V = 1855.13 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 100 K
0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.895, T_max = 0.944
17368 measured reflections
4269 independent reflections
3581 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.17
4269 reflections
226 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.48 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.83 (1)	1.92 (1)	2.737 (2)	165 (3)
N1—H1⋯S2	0.88 (1)	2.14 (2)	2.913 (2)	147 (2)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536809006199/bt2881sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006199/bt2881Isup2.hkl

checkCIF report

Related literature top

For background, see: El Ashry et al. (2009).

Experimental top

To a solution of (2,4-dichlorophenylamino)-5,5-dimethyl-cyclohex-2-en-1-one (0.1 mol) in DMSO (20 ml) and sodium hydroxide (0.4 g) in water (1 ml), carbon disulfphide (0.3 mol) was added in the course of 30 minutes. The mixture was stirred for 20 min below 283 K, and then 2-bromoethanol (0.1 mol) was added drop wise at room temperature for 30 min. The reaction mixture was left for 24 h and then diluted with water (200 ml) and acidified with 10% hydrochloric acid. The resulting precipitate was collected by filtration, dried and purified on silica gel column (40% ethyl acetate in hexane) to give yellow crystal (34.5% yield; mp.424 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) plot of C₁₇H₁₉Cl₂NO₂S₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₁₇H₁₉Cl₂NO₂S₂	F(000) = 840
M_r = 404.35	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5593 reflections
a = 11.7310 (2) Å	θ = 2.3–28.2°
b = 14.0903 (2) Å	µ = 0.59 mm⁻¹
c = 12.0416 (2) Å	T = 100 K
β = 111.245 (1)°	Prism, orange
V = 1855.13 (5) Å³	0.40 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4269 independent reflections
Radiation source: fine-focus sealed tube	3581 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.895, T_max = 0.944	k = −18→18
17368 measured reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.0429P)² + 0.8915P] where P = (F_o² + 2F_c²)/3
4269 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 1.48 e Å⁻³
2 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₇H₁₉Cl₂NO₂S₂	V = 1855.13 (5) Å³
M_r = 404.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7310 (2) Å	µ = 0.59 mm⁻¹
b = 14.0903 (2) Å	T = 100 K
c = 12.0416 (2) Å	0.40 × 0.10 × 0.10 mm
β = 111.245 (1)°

Data collection top

Bruker SMART APEX diffractometer	4269 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3581 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.944	R_int = 0.031
17368 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 1.48 e Å⁻³
4269 reflections	Δρ_min = −0.49 e Å⁻³
226 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	0.50297 (4)	0.66542 (3)	0.81611 (4)	0.02438 (12)
Cl2	0.69365 (5)	0.33055 (4)	1.00864 (5)	0.02908 (13)
S1	−0.02899 (5)	0.74647 (4)	0.42522 (4)	0.02988 (14)
S2	0.11953 (5)	0.71791 (4)	0.68063 (4)	0.02937 (14)
O1	−0.05234 (12)	0.57916 (11)	0.32339 (12)	0.0255 (3)
O2	−0.14964 (14)	0.95304 (11)	0.58309 (13)	0.0302 (4)
H2	−0.123 (2)	0.954 (2)	0.6574 (9)	0.048 (8)*
N1	0.27644 (14)	0.55532 (12)	0.69084 (14)	0.0203 (3)
H1	0.250 (2)	0.6051 (12)	0.718 (2)	0.038 (7)*
C1	0.21902 (17)	0.53820 (13)	0.57550 (17)	0.0188 (4)
C2	0.26758 (19)	0.45827 (15)	0.52239 (17)	0.0239 (4)
H2A	0.2247	0.3989	0.5278	0.029*
H2B	0.3556	0.4495	0.5698	0.029*
C3	0.25180 (18)	0.47536 (15)	0.39220 (17)	0.0239 (4)
C4	0.11563 (19)	0.48819 (16)	0.32527 (18)	0.0266 (4)
H4A	0.1028	0.5110	0.2439	0.032*
H4B	0.0754	0.4255	0.3176	0.032*
C5	0.05389 (17)	0.55607 (14)	0.38206 (16)	0.0203 (4)
C6	0.11713 (16)	0.59172 (14)	0.50288 (16)	0.0191 (4)
C7	0.2972 (2)	0.38762 (17)	0.3452 (2)	0.0343 (5)
H7A	0.2836	0.3965	0.2606	0.051*
H7B	0.2523	0.3315	0.3549	0.051*
H7C	0.3848	0.3788	0.3901	0.051*
C8	0.3236 (2)	0.56243 (17)	0.3788 (2)	0.0326 (5)
H8A	0.3078	0.5734	0.2942	0.049*
H8B	0.4112	0.5516	0.4212	0.049*
H8C	0.2977	0.6181	0.4124	0.049*
C9	0.07364 (17)	0.67738 (14)	0.54093 (16)	0.0203 (4)
C10	−0.0347 (2)	0.85810 (15)	0.49607 (19)	0.0289 (5)
H10A	0.0452	0.8699	0.5604	0.035*
H10B	−0.0496	0.9099	0.4370	0.035*
C11	−0.13386 (19)	0.85877 (16)	0.5476 (2)	0.0293 (5)
H11A	−0.2114	0.8358	0.4873	0.035*
H11B	−0.1115	0.8158	0.6173	0.035*
C12	0.37500 (16)	0.50105 (14)	0.76960 (16)	0.0182 (4)
C13	0.48643 (17)	0.54444 (13)	0.83201 (16)	0.0175 (4)
C14	0.58495 (16)	0.49276 (14)	0.90679 (16)	0.0183 (4)
H14	0.6609	0.5228	0.9489	0.022*
C15	0.56972 (17)	0.39647 (14)	0.91836 (16)	0.0189 (4)
C16	0.45843 (18)	0.35196 (14)	0.86133 (17)	0.0216 (4)
H16	0.4491	0.2861	0.8727	0.026*
C17	0.36107 (17)	0.40498 (14)	0.78745 (17)	0.0217 (4)
H17	0.2841	0.3754	0.7486	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0248 (2)	0.0197 (2)	0.0274 (3)	0.00018 (18)	0.00800 (19)	0.00396 (18)
Cl2	0.0231 (2)	0.0295 (3)	0.0298 (3)	0.0102 (2)	0.0038 (2)	0.0088 (2)
S1	0.0367 (3)	0.0309 (3)	0.0171 (2)	0.0127 (2)	0.0039 (2)	0.0018 (2)
S2	0.0306 (3)	0.0345 (3)	0.0157 (2)	0.0153 (2)	−0.0004 (2)	−0.0050 (2)
O1	0.0188 (7)	0.0343 (8)	0.0179 (7)	0.0032 (6)	0.0001 (5)	−0.0036 (6)
O2	0.0316 (8)	0.0319 (8)	0.0202 (8)	0.0137 (7)	0.0011 (6)	−0.0012 (6)
N1	0.0167 (8)	0.0233 (9)	0.0166 (8)	0.0055 (7)	0.0009 (6)	−0.0029 (6)
C1	0.0163 (8)	0.0212 (9)	0.0179 (9)	0.0001 (7)	0.0051 (7)	−0.0012 (7)
C2	0.0247 (10)	0.0254 (10)	0.0199 (10)	0.0071 (8)	0.0062 (8)	−0.0008 (8)
C3	0.0234 (10)	0.0294 (11)	0.0178 (9)	0.0062 (8)	0.0063 (8)	−0.0033 (8)
C4	0.0253 (10)	0.0339 (11)	0.0178 (9)	0.0047 (9)	0.0045 (8)	−0.0074 (8)
C5	0.0199 (9)	0.0237 (10)	0.0152 (9)	−0.0006 (8)	0.0037 (7)	0.0002 (7)
C6	0.0165 (9)	0.0247 (10)	0.0142 (9)	0.0017 (7)	0.0031 (7)	−0.0015 (7)
C7	0.0358 (12)	0.0372 (13)	0.0290 (11)	0.0103 (10)	0.0107 (10)	−0.0094 (10)
C8	0.0306 (11)	0.0395 (13)	0.0313 (12)	0.0024 (10)	0.0155 (9)	−0.0023 (10)
C9	0.0154 (9)	0.0271 (10)	0.0160 (9)	0.0029 (7)	0.0027 (7)	−0.0006 (7)
C10	0.0365 (12)	0.0255 (10)	0.0234 (10)	0.0071 (9)	0.0093 (9)	0.0036 (8)
C11	0.0247 (10)	0.0307 (11)	0.0279 (11)	0.0055 (9)	0.0038 (9)	0.0000 (9)
C12	0.0157 (9)	0.0236 (9)	0.0137 (8)	0.0038 (7)	0.0033 (7)	−0.0014 (7)
C13	0.0192 (9)	0.0192 (9)	0.0152 (8)	0.0006 (7)	0.0075 (7)	0.0003 (7)
C14	0.0136 (8)	0.0248 (10)	0.0156 (9)	−0.0002 (7)	0.0043 (7)	−0.0001 (7)
C15	0.0182 (9)	0.0233 (9)	0.0144 (9)	0.0071 (7)	0.0048 (7)	0.0033 (7)
C16	0.0246 (10)	0.0188 (9)	0.0212 (10)	0.0015 (8)	0.0081 (8)	−0.0010 (7)
C17	0.0184 (9)	0.0245 (10)	0.0198 (9)	−0.0018 (8)	0.0042 (7)	−0.0039 (8)

Geometric parameters (Å, º) top

Cl1—C13	1.7341 (19)	C5—C6	1.462 (3)
Cl2—C15	1.7358 (18)	C6—C9	1.448 (3)
S1—C9	1.7671 (19)	C7—H7A	0.9800
S1—C10	1.802 (2)	C7—H7B	0.9800
S2—C9	1.6701 (19)	C7—H7C	0.9800
O1—C5	1.233 (2)	C8—H8A	0.9800
O2—C11	1.428 (3)	C8—H8B	0.9800
O2—H2	0.834 (10)	C8—H8C	0.9800
N1—C1	1.328 (2)	C10—C11	1.504 (3)
N1—C12	1.424 (2)	C10—H10A	0.9900
N1—H1	0.879 (10)	C10—H10B	0.9900
C1—C6	1.416 (3)	C11—H11A	0.9900
C1—C2	1.505 (3)	C11—H11B	0.9900
C2—C3	1.530 (3)	C12—C17	1.389 (3)
C2—H2A	0.9900	C12—C13	1.391 (3)
C2—H2B	0.9900	C13—C14	1.387 (3)
C3—C4	1.517 (3)	C14—C15	1.382 (3)
C3—C8	1.529 (3)	C14—H14	0.9500
C3—C7	1.533 (3)	C15—C16	1.385 (3)
C4—C5	1.505 (3)	C16—C17	1.385 (3)
C4—H4A	0.9900	C16—H16	0.9500
C4—H4B	0.9900	C17—H17	0.9500

C9—S1—C10	103.83 (10)	C3—C8—H8B	109.5
C11—O2—H2	106.8 (19)	H8A—C8—H8B	109.5
C1—N1—C12	125.53 (16)	C3—C8—H8C	109.5
C1—N1—H1	115.2 (17)	H8A—C8—H8C	109.5
C12—N1—H1	119.3 (17)	H8B—C8—H8C	109.5
N1—C1—C6	122.96 (17)	C6—C9—S2	125.58 (14)
N1—C1—C2	116.98 (16)	C6—C9—S1	115.29 (13)
C6—C1—C2	120.05 (16)	S2—C9—S1	118.99 (11)
C1—C2—C3	113.19 (16)	C11—C10—S1	111.57 (16)
C1—C2—H2A	108.9	C11—C10—H10A	109.3
C3—C2—H2A	108.9	S1—C10—H10A	109.3
C1—C2—H2B	108.9	C11—C10—H10B	109.3
C3—C2—H2B	108.9	S1—C10—H10B	109.3
H2A—C2—H2B	107.8	H10A—C10—H10B	108.0
C4—C3—C8	111.24 (18)	O2—C11—C10	109.44 (18)
C4—C3—C2	106.04 (16)	O2—C11—H11A	109.8
C8—C3—C2	111.58 (17)	C10—C11—H11A	109.8
C4—C3—C7	109.87 (17)	O2—C11—H11B	109.8
C8—C3—C7	109.25 (18)	C10—C11—H11B	109.8
C2—C3—C7	108.80 (17)	H11A—C11—H11B	108.2
C5—C4—C3	114.95 (16)	C17—C12—C13	118.99 (17)
C5—C4—H4A	108.5	C17—C12—N1	120.92 (17)
C3—C4—H4A	108.5	C13—C12—N1	120.07 (17)
C5—C4—H4B	108.5	C14—C13—C12	121.26 (17)
C3—C4—H4B	108.5	C14—C13—Cl1	119.19 (14)
H4A—C4—H4B	107.5	C12—C13—Cl1	119.55 (14)
O1—C5—C6	121.51 (17)	C15—C14—C13	118.24 (17)
O1—C5—C4	117.40 (17)	C15—C14—H14	120.9
C6—C5—C4	121.08 (16)	C13—C14—H14	120.9
C1—C6—C9	124.33 (17)	C14—C15—C16	121.83 (17)
C1—C6—C5	116.24 (17)	C14—C15—Cl2	118.61 (14)
C9—C6—C5	119.43 (16)	C16—C15—Cl2	119.55 (15)
C3—C7—H7A	109.5	C15—C16—C17	118.94 (18)
C3—C7—H7B	109.5	C15—C16—H16	120.5
H7A—C7—H7B	109.5	C17—C16—H16	120.5
C3—C7—H7C	109.5	C16—C17—C12	120.60 (18)
H7A—C7—H7C	109.5	C16—C17—H17	119.7
H7B—C7—H7C	109.5	C12—C17—H17	119.7
C3—C8—H8A	109.5

C12—N1—C1—C6	176.51 (18)	C1—C6—C9—S1	164.93 (16)
C12—N1—C1—C2	−4.0 (3)	C5—C6—C9—S1	−15.1 (2)
N1—C1—C2—C3	−147.64 (18)	C10—S1—C9—C6	−166.31 (15)
C6—C1—C2—C3	31.9 (3)	C10—S1—C9—S2	9.62 (15)
C1—C2—C3—C4	−58.6 (2)	C9—S1—C10—C11	−89.89 (16)
C1—C2—C3—C8	62.7 (2)	S1—C10—C11—O2	−169.55 (13)
C1—C2—C3—C7	−176.75 (17)	C1—N1—C12—C17	−59.2 (3)
C8—C3—C4—C5	−73.5 (2)	C1—N1—C12—C13	122.2 (2)
C2—C3—C4—C5	48.0 (2)	C17—C12—C13—C14	3.2 (3)
C7—C3—C4—C5	165.45 (19)	N1—C12—C13—C14	−178.21 (17)
C3—C4—C5—O1	170.11 (18)	C17—C12—C13—Cl1	−176.94 (14)
C3—C4—C5—C6	−10.9 (3)	N1—C12—C13—Cl1	1.7 (2)
N1—C1—C6—C9	8.1 (3)	C12—C13—C14—C15	−0.2 (3)
C2—C1—C6—C9	−171.37 (18)	Cl1—C13—C14—C15	179.86 (14)
N1—C1—C6—C5	−171.89 (18)	C13—C14—C15—C16	−2.5 (3)
C2—C1—C6—C5	8.6 (3)	C13—C14—C15—Cl2	178.31 (14)
O1—C5—C6—C1	159.28 (18)	C14—C15—C16—C17	2.3 (3)
C4—C5—C6—C1	−19.6 (3)	Cl2—C15—C16—C17	−178.56 (15)
O1—C5—C6—C9	−20.7 (3)	C15—C16—C17—C12	0.7 (3)
C4—C5—C6—C9	160.35 (18)	C13—C12—C17—C16	−3.4 (3)
C1—C6—C9—S2	−10.7 (3)	N1—C12—C17—C16	177.98 (17)
C5—C6—C9—S2	169.31 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.83 (1)	1.92 (1)	2.737 (2)	165 (3)
N1—H1···S2	0.88 (1)	2.14 (2)	2.913 (2)	147 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉Cl₂NO₂S₂
M_r	404.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.7310 (2), 14.0903 (2), 12.0416 (2)
β (°)	111.245 (1)
V (Å³)	1855.13 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.895, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	17368, 4269, 3581
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.098, 1.17
No. of reflections	4269
No. of parameters	226
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.48, −0.49

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
O2—H2···O1ⁱ	0.83 (1)	1.92 (1)	2.737 (2)	165 (3)
N1—H1···S2	0.88 (1)	2.14 (2)	2.913 (2)	147 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

We thank the Higher Education Commission of Pakistan 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., Raza Shah, M. & Ng, S. W. (2009). Acta Cryst. E65, o597. 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 3| March 2009| Page o602

doi:10.1107/S1600536809006199

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

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

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