Benzyl 2-(4-bromo­anilino)-4,4-dimethyl-6-oxocyclo­hex-1-enecarbodithio­ate: first triclinic polymorph

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

doi:10.1107/S160053680900614X

organic compounds

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Volume 65| Part 3| March 2009| Page o597

doi:10.1107/S160053680900614X

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Benzyl 2-(4-bromoanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate: first triclinic polymorph

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 19 February 2009; accepted 19 February 2009; online 25 February 2009)

The six-membered cyclohexene ring in the title compound, C₂₂H₂₂BrNOS₂, adopts an envelope conformation, with the C atom bearing the two methyl groups representing the flap. This atom deviates by 0.686 (4) Å from the plane passing through the other five atoms of the ring (r.m.s. deviation = 0.025 Å). The molecular conformation is stabilized by an intramolecular N—H⋯S hydrogen bond.

Related literature

For previous work on this topic, see: El Ashry et al. (2005a ,b , 2006 , 2008a ,b ); El Ashry, Kassem et al. (2009 ). For the use of enamines in heterocyclic synthesis, see: Tominaga (1989 ); Tominaga et al. (1991 ). For another triclinic polymorph of the title compound, see El Ashry, Amer et al. (2009 ).

Experimental

Crystal data

C₂₂H₂₂BrNOS₂
M_r = 460.44
Triclinic, $[P \overline 1]$
a = 9.3030 (3) Å
b = 9.8099 (3) Å
c = 12.3538 (4) Å
α = 73.464 (2)°
β = 72.391 (2)°
γ = 89.916 (2)°
V = 1025.73 (6) Å³
Z = 2
Mo Kα radiation
μ = 2.22 mm⁻¹
T = 100 K
0.40 × 0.04 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.684, T_max = 0.917
9757 measured reflections
4709 independent reflections
3490 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.077
S = 0.99
4709 reflections
250 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2	0.88 (1)	2.10 (2)	2.905 (2)	151 (3)

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/S160053680900614X/bt2876sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900614X/bt2876Isup2.hkl

checkCIF report

Comment top

The enaminodithiocarboxylates are a class of compounds of crucial significance for designing functionalized molecules that are suitable for studying the biological activity of potentially useful chemicals. They are also important reactants in the synthesis of heterocyclic compounds (Tominaga, 1989; Tominaga et al., 1991). Our interest in such class of compounds revolves around new glycosyl donors (El Ashry et al., 2005a, 2005b, 2006, 2008a, 2008b, El Ashry, Kassem et al.2009). The title compound is to be used in a model study to understand the scope of the reaction that uses cyclic enaminones. A possibility exists that the representative title compound can lead to a fused cyclized product.

Related literature top

For previous work on this topic, see: El Ashry et al. (2005a,b, 2006, 2008a,b); El Ashry, Kassem et al. (2009). For the use of enamines in heterocyclic synthesis, see: Tominaga (1989); Tominaga et al. (1991). For another triclinic polymorph of the title compound, see El Ashry, Amer et al. (2009).

Experimental top

To a solution of 3-(4-bromoanilino)-5,5-dimethyl-cyclohex-2-en-1-one (0.1 mol) in DMSO (20 ml) and sodium hydroxide (0.1 mol) in water (1 ml) was added carbon disulphide (0.3 mol). The mixture was kept at 263 K for 20 min. Benzyl bromide (0.1 mol) was added. The mixture was left for 24 h, after which it was quenched with water (200 ml) and then acidified with 10% hydrochloric acid. The resulting precipitate was collected by filtration, dried and purified on a silica gel column (30% ethyl acetate in hexane) to give orange crystals (40% yield, mp 458 K). HRMS for C₂₂H₂₂BrNOS₂, calc.: 459.0326, found, m/z: 459.0316.

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 C₂₂H₂₂BrNOS₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Benzyl 2-(4-bromoanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate top

Crystal data top

C₂₂H₂₂BrNOS₂	Z = 2
M_r = 460.44	F(000) = 472
Triclinic, P1	D_x = 1.491 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3030 (3) Å	Cell parameters from 2124 reflections
b = 9.8099 (3) Å	θ = 2.4–25.2°
c = 12.3538 (4) Å	µ = 2.22 mm⁻¹
α = 73.464 (2)°	T = 100 K
β = 72.391 (2)°	Prism, yellow
γ = 89.916 (2)°	0.40 × 0.04 × 0.04 mm
V = 1025.73 (6) Å³

Data collection top

Bruker SMART APEX diffractometer	4709 independent reflections
Radiation source: fine-focus sealed tube	3490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.684, T_max = 0.917	k = −12→12
9757 measured reflections	l = −16→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) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0236P)² + 0.5453P] where P = (F_o² + 2F_c²)/3
4709 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.47 e Å⁻³
1 restraint	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₂H₂₂BrNOS₂	γ = 89.916 (2)°
M_r = 460.44	V = 1025.73 (6) Å³
Triclinic, P1	Z = 2
a = 9.3030 (3) Å	Mo Kα radiation
b = 9.8099 (3) Å	µ = 2.22 mm⁻¹
c = 12.3538 (4) Å	T = 100 K
α = 73.464 (2)°	0.40 × 0.04 × 0.04 mm
β = 72.391 (2)°

Data collection top

Bruker SMART APEX diffractometer	4709 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3490 reflections with I > 2σ(I)
T_min = 0.684, T_max = 0.917	R_int = 0.039
9757 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.47 e Å⁻³
4709 reflections	Δρ_min = −0.38 e Å⁻³
250 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
Br1	0.36770 (4)	0.20219 (3)	1.10143 (3)	0.02491 (9)
S1	0.64466 (8)	1.01099 (7)	0.25672 (6)	0.01823 (16)
S2	0.74397 (8)	0.76685 (8)	0.41055 (6)	0.02190 (17)
O1	0.3727 (2)	1.0432 (2)	0.34593 (18)	0.0319 (5)
N1	0.4826 (3)	0.6419 (2)	0.6181 (2)	0.0182 (5)
H1	0.5775 (16)	0.658 (3)	0.571 (2)	0.035 (10)*
C1	0.3918 (3)	0.7277 (3)	0.5732 (2)	0.0153 (6)
C2	0.2258 (3)	0.7000 (3)	0.6438 (2)	0.0181 (6)
H2A	0.2056	0.7509	0.7048	0.022*
H2B	0.2024	0.5966	0.6860	0.022*
C3	0.1189 (3)	0.7459 (3)	0.5701 (2)	0.0179 (6)
C4	0.1689 (3)	0.9016 (3)	0.5000 (2)	0.0196 (6)
H4A	0.1096	0.9325	0.4443	0.024*
H4B	0.1437	0.9594	0.5560	0.024*
C5	0.3345 (3)	0.9339 (3)	0.4300 (2)	0.0192 (6)
C6	0.4459 (3)	0.8392 (3)	0.4637 (2)	0.0149 (6)
C7	0.1277 (3)	0.6549 (3)	0.4872 (3)	0.0267 (7)
H7A	0.0547	0.6832	0.4439	0.040*
H7B	0.1040	0.5540	0.5340	0.040*
H7C	0.2302	0.6689	0.4304	0.040*
C8	−0.0436 (3)	0.7327 (3)	0.6537 (3)	0.0256 (7)
H8A	−0.1117	0.7662	0.6067	0.038*
H8B	−0.0483	0.7909	0.7072	0.038*
H8C	−0.0747	0.6326	0.7007	0.038*
C9	0.6016 (3)	0.8658 (3)	0.3878 (2)	0.0158 (6)
C10	0.8407 (3)	0.9962 (3)	0.1768 (2)	0.0211 (6)
H10A	0.9090	1.0131	0.2204	0.025*
H10B	0.8531	0.9004	0.1655	0.025*
C11	0.8740 (3)	1.1104 (3)	0.0584 (2)	0.0198 (6)
C12	0.8062 (3)	1.0952 (3)	−0.0244 (3)	0.0243 (7)
H12	0.7392	1.0127	−0.0055	0.029*
C13	0.8346 (3)	1.1978 (3)	−0.1334 (3)	0.0290 (7)
H13	0.7881	1.1855	−0.1891	0.035*
C14	0.9310 (4)	1.3184 (3)	−0.1609 (3)	0.0306 (8)
H14	0.9511	1.3891	−0.2358	0.037*
C15	0.9979 (4)	1.3362 (3)	−0.0802 (3)	0.0306 (8)
H15	1.0637	1.4194	−0.0992	0.037*
C16	0.9693 (3)	1.2323 (3)	0.0298 (3)	0.0250 (7)
H16	1.0156	1.2455	0.0853	0.030*
C17	0.4444 (3)	0.5381 (3)	0.7324 (2)	0.0168 (6)
C18	0.3865 (3)	0.5766 (3)	0.8354 (2)	0.0203 (6)
H18	0.3649	0.6724	0.8308	0.024*
C19	0.3599 (3)	0.4755 (3)	0.9452 (3)	0.0212 (6)
H19	0.3188	0.5013	1.0163	0.025*
C20	0.3937 (3)	0.3364 (3)	0.9507 (2)	0.0197 (6)
C21	0.4509 (3)	0.2970 (3)	0.8484 (2)	0.0202 (6)
H21	0.4732	0.2014	0.8531	0.024*
C22	0.4755 (3)	0.3981 (3)	0.7388 (2)	0.0202 (6)
H22	0.5137	0.3715	0.6678	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02959 (18)	0.02257 (16)	0.01791 (15)	−0.00197 (12)	−0.00961 (12)	0.00337 (12)
S1	0.0185 (4)	0.0162 (3)	0.0149 (3)	0.0032 (3)	−0.0018 (3)	−0.0005 (3)
S2	0.0162 (4)	0.0236 (4)	0.0205 (4)	0.0054 (3)	−0.0041 (3)	−0.0002 (3)
O1	0.0258 (12)	0.0285 (12)	0.0251 (12)	0.0089 (10)	−0.0013 (9)	0.0094 (9)
N1	0.0154 (13)	0.0186 (12)	0.0158 (12)	0.0009 (10)	−0.0043 (10)	0.0014 (10)
C1	0.0181 (15)	0.0129 (13)	0.0176 (14)	0.0016 (11)	−0.0075 (12)	−0.0066 (11)
C2	0.0177 (15)	0.0172 (14)	0.0153 (14)	0.0004 (11)	−0.0040 (11)	−0.0001 (11)
C3	0.0163 (15)	0.0191 (14)	0.0175 (14)	0.0018 (12)	−0.0060 (12)	−0.0035 (12)
C4	0.0173 (15)	0.0186 (14)	0.0209 (15)	0.0046 (12)	−0.0054 (12)	−0.0036 (12)
C5	0.0205 (15)	0.0197 (15)	0.0154 (14)	0.0034 (12)	−0.0049 (12)	−0.0027 (12)
C6	0.0153 (14)	0.0166 (13)	0.0126 (13)	0.0035 (11)	−0.0060 (11)	−0.0023 (11)
C7	0.0238 (17)	0.0280 (16)	0.0337 (18)	0.0017 (13)	−0.0137 (14)	−0.0124 (14)
C8	0.0162 (15)	0.0254 (16)	0.0288 (17)	0.0011 (13)	−0.0051 (13)	−0.0004 (13)
C9	0.0185 (14)	0.0148 (13)	0.0134 (13)	0.0004 (11)	−0.0048 (11)	−0.0034 (11)
C10	0.0168 (15)	0.0216 (15)	0.0199 (15)	0.0026 (12)	−0.0010 (12)	−0.0036 (12)
C11	0.0167 (15)	0.0192 (14)	0.0190 (15)	0.0046 (12)	0.0003 (12)	−0.0052 (12)
C12	0.0210 (16)	0.0254 (16)	0.0224 (16)	−0.0034 (13)	−0.0029 (13)	−0.0051 (13)
C13	0.0250 (17)	0.0389 (19)	0.0197 (16)	0.0040 (14)	−0.0079 (13)	−0.0026 (14)
C14	0.0350 (19)	0.0254 (17)	0.0206 (16)	0.0059 (15)	−0.0027 (14)	0.0032 (13)
C15	0.0343 (19)	0.0179 (15)	0.0315 (18)	−0.0040 (14)	−0.0017 (15)	−0.0042 (14)
C16	0.0258 (17)	0.0248 (16)	0.0229 (16)	0.0013 (13)	−0.0054 (13)	−0.0072 (13)
C17	0.0150 (14)	0.0180 (14)	0.0160 (14)	−0.0014 (11)	−0.0068 (11)	−0.0009 (11)
C18	0.0227 (16)	0.0164 (14)	0.0236 (15)	0.0029 (12)	−0.0106 (13)	−0.0054 (12)
C19	0.0236 (16)	0.0234 (15)	0.0189 (15)	0.0034 (13)	−0.0095 (12)	−0.0067 (12)
C20	0.0191 (15)	0.0189 (14)	0.0165 (14)	−0.0018 (12)	−0.0072 (12)	0.0033 (12)
C21	0.0220 (16)	0.0139 (14)	0.0232 (15)	0.0014 (12)	−0.0076 (12)	−0.0026 (12)
C22	0.0207 (15)	0.0221 (15)	0.0151 (14)	0.0040 (12)	−0.0037 (12)	−0.0035 (12)

Geometric parameters (Å, º) top

Br1—C20	1.895 (3)	C8—H8C	0.9800
S1—C9	1.763 (3)	C10—C11	1.511 (4)
S1—C10	1.820 (3)	C10—H10A	0.9900
S2—C9	1.686 (3)	C10—H10B	0.9900
O1—C5	1.224 (3)	C11—C16	1.384 (4)
N1—C1	1.321 (3)	C11—C12	1.394 (4)
N1—C17	1.427 (3)	C12—C13	1.383 (4)
N1—H1	0.884 (10)	C12—H12	0.9500
C1—C6	1.424 (3)	C13—C14	1.382 (4)
C1—C2	1.506 (4)	C13—H13	0.9500
C2—C3	1.527 (4)	C14—C15	1.373 (4)
C2—H2A	0.9900	C14—H14	0.9500
C2—H2B	0.9900	C15—C16	1.396 (4)
C3—C4	1.518 (4)	C15—H15	0.9500
C3—C7	1.524 (4)	C16—H16	0.9500
C3—C8	1.532 (4)	C17—C18	1.382 (4)
C4—C5	1.504 (4)	C17—C22	1.388 (4)
C4—H4A	0.9900	C18—C19	1.385 (4)
C4—H4B	0.9900	C18—H18	0.9500
C5—C6	1.465 (4)	C19—C20	1.388 (4)
C6—C9	1.444 (4)	C19—H19	0.9500
C7—H7A	0.9800	C20—C21	1.379 (4)
C7—H7B	0.9800	C21—C22	1.385 (4)
C7—H7C	0.9800	C21—H21	0.9500
C8—H8A	0.9800	C22—H22	0.9500
C8—H8B	0.9800

C9—S1—C10	104.06 (13)	C6—C9—S1	116.85 (19)
C1—N1—C17	127.3 (2)	S2—C9—S1	117.21 (16)
C1—N1—H1	113 (2)	C11—C10—S1	104.63 (18)
C17—N1—H1	120 (2)	C11—C10—H10A	110.8
N1—C1—C6	122.4 (2)	S1—C10—H10A	110.8
N1—C1—C2	116.2 (2)	C11—C10—H10B	110.8
C6—C1—C2	121.4 (2)	S1—C10—H10B	110.8
C1—C2—C3	114.7 (2)	H10A—C10—H10B	108.9
C1—C2—H2A	108.6	C16—C11—C12	118.4 (3)
C3—C2—H2A	108.6	C16—C11—C10	121.7 (3)
C1—C2—H2B	108.6	C12—C11—C10	119.9 (3)
C3—C2—H2B	108.6	C13—C12—C11	121.2 (3)
H2A—C2—H2B	107.6	C13—C12—H12	119.4
C4—C3—C7	111.0 (2)	C11—C12—H12	119.4
C4—C3—C2	106.0 (2)	C14—C13—C12	119.6 (3)
C7—C3—C2	111.0 (2)	C14—C13—H13	120.2
C4—C3—C8	109.5 (2)	C12—C13—H13	120.2
C7—C3—C8	109.9 (2)	C15—C14—C13	120.1 (3)
C2—C3—C8	109.4 (2)	C15—C14—H14	119.9
C5—C4—C3	115.2 (2)	C13—C14—H14	119.9
C5—C4—H4A	108.5	C14—C15—C16	120.2 (3)
C3—C4—H4A	108.5	C14—C15—H15	119.9
C5—C4—H4B	108.5	C16—C15—H15	119.9
C3—C4—H4B	108.5	C11—C16—C15	120.4 (3)
H4A—C4—H4B	107.5	C11—C16—H16	119.8
O1—C5—C6	121.5 (3)	C15—C16—H16	119.8
O1—C5—C4	117.6 (2)	C18—C17—C22	120.1 (2)
C6—C5—C4	120.9 (2)	C18—C17—N1	121.1 (2)
C1—C6—C9	124.3 (2)	C22—C17—N1	118.6 (2)
C1—C6—C5	116.5 (2)	C17—C18—C19	120.0 (3)
C9—C6—C5	119.2 (2)	C17—C18—H18	120.0
C3—C7—H7A	109.5	C19—C18—H18	120.0
C3—C7—H7B	109.5	C18—C19—C20	119.4 (3)
H7A—C7—H7B	109.5	C18—C19—H19	120.3
C3—C7—H7C	109.5	C20—C19—H19	120.3
H7A—C7—H7C	109.5	C21—C20—C19	120.9 (3)
H7B—C7—H7C	109.5	C21—C20—Br1	120.2 (2)
C3—C8—H8A	109.5	C19—C20—Br1	118.9 (2)
C3—C8—H8B	109.5	C20—C21—C22	119.4 (3)
H8A—C8—H8B	109.5	C20—C21—H21	120.3
C3—C8—H8C	109.5	C22—C21—H21	120.3
H8A—C8—H8C	109.5	C21—C22—C17	120.1 (3)
H8B—C8—H8C	109.5	C21—C22—H22	120.0
C6—C9—S2	125.9 (2)	C17—C22—H22	120.0

C17—N1—C1—C6	172.3 (3)	C10—S1—C9—S2	4.9 (2)
C17—N1—C1—C2	−8.4 (4)	C9—S1—C10—C11	174.14 (19)
N1—C1—C2—C3	−152.6 (2)	S1—C10—C11—C16	109.1 (3)
C6—C1—C2—C3	26.7 (4)	S1—C10—C11—C12	−69.9 (3)
C1—C2—C3—C4	−53.7 (3)	C16—C11—C12—C13	1.0 (4)
C1—C2—C3—C7	66.9 (3)	C10—C11—C12—C13	−179.9 (3)
C1—C2—C3—C8	−171.7 (2)	C11—C12—C13—C14	−0.5 (5)
C7—C3—C4—C5	−68.6 (3)	C12—C13—C14—C15	−0.2 (5)
C2—C3—C4—C5	52.0 (3)	C13—C14—C15—C16	0.3 (5)
C8—C3—C4—C5	169.9 (2)	C12—C11—C16—C15	−0.8 (4)
C3—C4—C5—O1	158.1 (3)	C10—C11—C16—C15	−179.9 (3)
C3—C4—C5—C6	−23.4 (4)	C14—C15—C16—C11	0.2 (5)
N1—C1—C6—C9	3.5 (4)	C1—N1—C17—C18	−58.6 (4)
C2—C1—C6—C9	−175.8 (2)	C1—N1—C17—C22	125.4 (3)
N1—C1—C6—C5	−174.7 (2)	C22—C17—C18—C19	0.2 (4)
C2—C1—C6—C5	6.0 (4)	N1—C17—C18—C19	−175.6 (2)
O1—C5—C6—C1	170.7 (3)	C17—C18—C19—C20	0.8 (4)
C4—C5—C6—C1	−7.8 (4)	C18—C19—C20—C21	−1.1 (4)
O1—C5—C6—C9	−7.6 (4)	C18—C19—C20—Br1	176.4 (2)
C4—C5—C6—C9	173.9 (2)	C19—C20—C21—C22	0.3 (4)
C1—C6—C9—S2	3.1 (4)	Br1—C20—C21—C22	−177.1 (2)
C5—C6—C9—S2	−178.7 (2)	C20—C21—C22—C17	0.7 (4)
C1—C6—C9—S1	−179.3 (2)	C18—C17—C22—C21	−1.0 (4)
C5—C6—C9—S1	−1.2 (3)	N1—C17—C22—C21	174.9 (2)
C10—S1—C9—C6	−172.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2	0.88 (1)	2.10 (2)	2.905 (2)	151 (3)

Experimental details

Crystal data
Chemical formula	C₂₂H₂₂BrNOS₂
M_r	460.44
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.3030 (3), 9.8099 (3), 12.3538 (4)
α, β, γ (°)	73.464 (2), 72.391 (2), 89.916 (2)
V (Å³)	1025.73 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.22
Crystal size (mm)	0.40 × 0.04 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.684, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	9757, 4709, 3490
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.077, 0.99
No. of reflections	4709
No. of parameters	250
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.38

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	0.88 (1)	2.10 (2)	2.905 (2)	151 (3)

Acknowledgements

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

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El Ashry, E. S. H., Awad, L. F., Abdel Hamid, H. M. & Atta, A. I. (2005a). J. Carbohydr. Chem. 24, 745–753. Web of Science CrossRef CAS Google Scholar
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Volume 65| Part 3| March 2009| Page o597

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

Benzyl 2-(4-bromo­anilino)-4,4-di­methyl-6-oxo­cyclo­hex-1-enecarbodi­thio­ate: first triclinic polymorph

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Benzyl 2-(4-bromoanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate: first triclinic polymorph