3,3-Bis(4-bromo­phenyl­sulfan­yl)-1-methyl­piperidin-2-one

Zukerman-Schpector, J.; Olivato, P.R.; Cerqueira Jr, C.R.; Contieri, B.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813006995

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o556

doi:10.1107/S1600536813006995

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3,3-Bis(4-bromophenylsulfanyl)-1-methylpiperidin-2-one

Julio Zukerman-Schpector,^a ^* Paulo R. Olivato,^b Carlos R. Cerqueira Jr,^b Bruna Contieri,^b Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c

^aDepartmento de Química, Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos-SP, Brazil, ^bChemistry Institute, University of São Paulo, 05508-000 São Paulo, SP, Brazil, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: julio@power.ufscar.br

(Received 12 March 2013; accepted 13 March 2013; online 20 March 2013)

In the title compound, C₁₈H₁₇Br₂NOS₂, the conformation of the piperidin-2-one ring is based on a half-chair with the methylene C atom diagonally opposite the N atom being 0.649 (3) Å above the plane of the remaining five atoms (r.m.s. deviation = 0.1205 Å). The S atoms occupy axial and bisectional positions, and the dihedral angle between the benzene rings of 59.95 (11)° indicates a splayed disposition. Helical supramolecular chains along the b axis sustained by C—H⋯O interactions is the major feature of the crystal packing. The chains are connected into a three-dimensional architecture by C—H⋯Br and C—H⋯π interactions.

Related literature

For background to the chemistry and structures of β-thio-carbonyl compounds, see: Zukerman-Schpector et al. (2009 ); Vinhato (2007 ); Vinhato et al. (2011 ); Olivato et al. (2012 , 2013 ). For the synthesis, see: Olivato et al. (2013). For ring conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₁₇Br₂NOS₂
M_r = 487.27
Monoclinic, P 2₁ /n
a = 7.8777 (1) Å
b = 9.6481 (1) Å
c = 24.6757 (3) Å
β = 93.190 (1)°
V = 1872.57 (4) Å³
Z = 4
Cu Kα radiation
μ = 7.61 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.05 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.298, T_max = 1.000
18656 measured reflections
3916 independent reflections
3715 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.077
S = 1.10
3916 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −1.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Br2ⁱ	0.95	2.87	3.744 (2)	154
C11—H11⋯O1ⁱⁱ	0.95	2.27	3.195 (3)	163
C1—H1B⋯Cg1ⁱ	0.98	2.86	3.660 (3)	139
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813006995/hg5299sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006995/hg5299Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006995/hg5299Isup3.cml

checkCIF report

Comment top

The title compound (I), Fig. 1, was studied as a part of an on-going investigation of conformational and electronic interactions in β-thio-carbonyl compounds, e.g. N,N-diethyl-2-[(4'-substituted) phenylthio]acetamides, N,N-diethyl-2-[(4'-substituted) phenylsulfonyl]acetamides and 3,3-bis[(4'-substituted phenylsulfany)]-1-methyl-2-piperidinones using spectroscopic, theoretical and X-ray diffraction methods (Vinhato, 2007; Zukerman-Schpector et al., 2009; Vinhato et al., 2011; Olivato et al., 2012; Olivato et al., 2013).

In (I), the conformation of the six-membered piperidin-2-one ring is highly distorted with the best description being one based on a half-chair with the C4 atom lying 0.649 (3) Å above the plane of the remaining five atoms (r.m.s. deviation = 0.1205 Å), with puckering parameters: q₂ = 0.463 (2) Å and q₃ = 0.275 (2) Å, and amplitudes: Q = 0.539 (2) Å, θ = 59.4 (2)° and ϕ₂ = 214.7 (3)° (Cremer & Pople, 1975). The carbonyl-O1 and methyl-C1 atom occupy equatorial positions with respect to the piperidinyl ring while the S1 and S2 atoms are axial and bisectional, respectively. The dihedral angle between the benzene rings is 59.95 (11)°, indicating a splayed disposition.

The crystal packing features helical supramolecular chains along the b axis sustained by rather strong C—H···O interactions, Fig. 2 and Table 1. These are consolidated into a three-dimensional architecture by C—H···Br and C—H···π interactions, Fig. 3 and Table 1.

Related literature top

For background to the chemistry and structures of β-thio-carbonyl compounds, see: Zukerman-Schpector et al. (2009); Vinhato (2007); Vinhato et al. (2011); Olivato et al. (2012, 2013). For the synthesis, see: Olivato et al. (2013). For ring conformational analysis, see: Cremer & Pople (1975).

Experimental top

The preparation of the title compound was recently described (Olivato et al., 2013). Suitable crystals were obtained by vapour diffusion of n-hexane into a chloroform solution at 283 K.; M.pt: 383–385 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of (I) showing atom labelling and displacement ellipsoids at the 50% probability level.
	Fig. 2. Helical supramolecular chain along the b axis sustained by C—H···.O interactions (blue dashed lines).
	Fig. 3. View in projection down the b axis of the unit-cell contents. The C—H···O, C—H···Br and C—H···π interactions are shown as blue, orange and purple dashed lines, respectively.

3,3-Bis(4-bromophenylsulfanyl)-1-methylpiperidin-2-one top

Crystal data top

C₁₈H₁₇Br₂NOS₂	F(000) = 968
M_r = 487.27	D_x = 1.728 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 10597 reflections
a = 7.8777 (1) Å	θ = 3.6–76.5°
b = 9.6481 (1) Å	µ = 7.61 mm⁻¹
c = 24.6757 (3) Å	T = 100 K
β = 93.190 (1)°	Prism, colourless
V = 1872.57 (4) Å³	0.25 × 0.25 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3916 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3715 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.7°, θ_min = 3.6°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→12
T_min = 0.298, T_max = 1.000	l = −31→30
18656 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0402P)² + 1.5955P] where P = (F_o² + 2F_c²)/3
3916 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −1.26 e Å⁻³

Crystal data top

C₁₈H₁₇Br₂NOS₂	V = 1872.57 (4) Å³
M_r = 487.27	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 7.8777 (1) Å	µ = 7.61 mm⁻¹
b = 9.6481 (1) Å	T = 100 K
c = 24.6757 (3) Å	0.25 × 0.25 × 0.05 mm
β = 93.190 (1)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3916 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3715 reflections with I > 2σ(I)
T_min = 0.298, T_max = 1.000	R_int = 0.038
18656 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.10	Δρ_max = 0.71 e Å⁻³
3916 reflections	Δρ_min = −1.26 e Å⁻³
218 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Br1	0.20835 (4)	0.58290 (3)	0.025429 (10)	0.02829 (9)
Br2	0.82389 (3)	0.31232 (3)	0.521415 (11)	0.03241 (9)
S1	0.43546 (6)	0.86583 (5)	0.25378 (2)	0.01528 (11)
S2	0.39439 (6)	0.64897 (5)	0.33476 (2)	0.01610 (11)
O1	0.6089 (2)	0.90775 (16)	0.36438 (6)	0.0190 (3)
N1	0.8407 (2)	0.81429 (19)	0.32947 (7)	0.0166 (4)
C1	0.9475 (3)	0.8914 (3)	0.36927 (10)	0.0229 (5)
H1A	0.9052	0.8781	0.4055	0.034*
H1B	0.9443	0.9903	0.3601	0.034*
H1C	1.0648	0.8577	0.3689	0.034*
C2	0.6716 (3)	0.8271 (2)	0.33253 (8)	0.0144 (4)
C3	0.5560 (3)	0.7345 (2)	0.29522 (8)	0.0132 (4)
C4	0.6530 (3)	0.6307 (2)	0.26235 (8)	0.0143 (4)
H4A	0.5778	0.5947	0.2321	0.017*
H4B	0.6897	0.5516	0.2857	0.017*
C5	0.8078 (3)	0.6999 (2)	0.23983 (9)	0.0168 (4)
H5A	0.8652	0.6347	0.2159	0.020*
H5B	0.7722	0.7825	0.2182	0.020*
C6	0.9284 (3)	0.7424 (2)	0.28685 (9)	0.0195 (4)
H6A	0.9853	0.6588	0.3024	0.023*
H6B	1.0172	0.8040	0.2733	0.023*
C7	0.3782 (3)	0.7802 (2)	0.19177 (8)	0.0138 (4)
C8	0.4438 (3)	0.8300 (2)	0.14454 (9)	0.0183 (4)
H8	0.5235	0.9040	0.1463	0.022*
C9	0.3934 (3)	0.7720 (2)	0.09462 (9)	0.0208 (4)
H9	0.4372	0.8061	0.0621	0.025*
C10	0.2776 (3)	0.6631 (2)	0.09327 (9)	0.0171 (4)
C11	0.2116 (3)	0.6111 (2)	0.13980 (9)	0.0167 (4)
H11	0.1333	0.5361	0.1379	0.020*
C12	0.2618 (3)	0.6707 (2)	0.18945 (9)	0.0154 (4)
H12	0.2168	0.6369	0.2219	0.018*
C13	0.5212 (3)	0.5553 (2)	0.38409 (9)	0.0163 (4)
C14	0.5898 (3)	0.6240 (2)	0.42994 (9)	0.0208 (4)
H14	0.5735	0.7211	0.4336	0.025*
C15	0.6815 (3)	0.5517 (3)	0.47026 (9)	0.0239 (5)
H15	0.7290	0.5986	0.5014	0.029*
C16	0.7031 (3)	0.4095 (3)	0.46455 (10)	0.0222 (5)
C17	0.6353 (3)	0.3388 (2)	0.41976 (10)	0.0228 (5)
H17	0.6504	0.2415	0.4166	0.027*
C18	0.5445 (3)	0.4126 (2)	0.37925 (9)	0.0193 (4)
H18	0.4980	0.3654	0.3481	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04084 (17)	0.02690 (14)	0.01606 (13)	−0.00348 (10)	−0.00800 (10)	−0.00344 (9)
Br2	0.03033 (15)	0.04426 (17)	0.02278 (14)	0.01094 (11)	0.00269 (10)	0.01732 (11)
S1	0.0192 (2)	0.0127 (2)	0.0134 (2)	0.00287 (17)	−0.00357 (18)	−0.00037 (17)
S2	0.0128 (2)	0.0221 (2)	0.0133 (2)	−0.00130 (18)	−0.00071 (17)	0.00314 (18)
O1	0.0211 (7)	0.0191 (7)	0.0165 (8)	0.0035 (6)	−0.0020 (6)	−0.0051 (6)
N1	0.0158 (9)	0.0185 (9)	0.0153 (9)	−0.0012 (7)	−0.0013 (7)	−0.0003 (7)
C1	0.0186 (10)	0.0263 (11)	0.0230 (11)	−0.0046 (9)	−0.0066 (8)	−0.0012 (9)
C2	0.0170 (10)	0.0129 (9)	0.0131 (9)	0.0011 (7)	−0.0013 (7)	0.0025 (7)
C3	0.0143 (9)	0.0127 (9)	0.0123 (9)	0.0005 (7)	−0.0006 (7)	0.0004 (7)
C4	0.0176 (9)	0.0122 (9)	0.0130 (9)	0.0014 (7)	0.0004 (7)	−0.0002 (7)
C5	0.0198 (10)	0.0161 (9)	0.0149 (10)	0.0028 (8)	0.0048 (8)	0.0016 (7)
C6	0.0141 (10)	0.0211 (10)	0.0235 (11)	0.0013 (8)	0.0032 (8)	−0.0003 (8)
C7	0.0141 (9)	0.0141 (9)	0.0128 (9)	0.0018 (7)	−0.0033 (7)	0.0002 (7)
C8	0.0177 (10)	0.0196 (10)	0.0170 (10)	−0.0052 (8)	−0.0032 (8)	0.0050 (8)
C9	0.0226 (11)	0.0263 (11)	0.0134 (10)	−0.0029 (9)	−0.0008 (8)	0.0051 (8)
C10	0.0189 (10)	0.0178 (10)	0.0140 (10)	0.0020 (8)	−0.0054 (8)	−0.0007 (8)
C11	0.0150 (9)	0.0152 (9)	0.0193 (10)	−0.0001 (8)	−0.0035 (8)	0.0008 (8)
C12	0.0151 (9)	0.0159 (9)	0.0152 (10)	0.0015 (7)	0.0010 (7)	0.0035 (7)
C13	0.0135 (9)	0.0214 (10)	0.0139 (10)	−0.0015 (8)	0.0006 (7)	0.0039 (8)
C14	0.0242 (11)	0.0221 (11)	0.0158 (10)	−0.0019 (9)	−0.0014 (8)	0.0017 (8)
C15	0.0281 (12)	0.0282 (12)	0.0150 (10)	−0.0042 (9)	−0.0031 (9)	0.0023 (9)
C16	0.0181 (10)	0.0298 (12)	0.0187 (11)	0.0019 (8)	0.0005 (8)	0.0119 (9)
C17	0.0227 (11)	0.0215 (11)	0.0247 (12)	0.0012 (9)	0.0052 (9)	0.0060 (9)
C18	0.0192 (10)	0.0203 (10)	0.0183 (10)	−0.0035 (8)	0.0018 (8)	0.0007 (8)

Geometric parameters (Å, º) top

Br1—C10	1.897 (2)	C6—H6B	0.9900
Br2—C16	1.899 (2)	C7—C8	1.387 (3)
S1—C7	1.775 (2)	C7—C12	1.398 (3)
S1—C3	1.856 (2)	C8—C9	1.391 (3)
S2—C13	1.778 (2)	C8—H8	0.9500
S2—C3	1.842 (2)	C9—C10	1.390 (3)
O1—C2	1.229 (3)	C9—H9	0.9500
N1—C2	1.344 (3)	C10—C11	1.381 (3)
N1—C1	1.461 (3)	C11—C12	1.391 (3)
N1—C6	1.465 (3)	C11—H11	0.9500
C1—H1A	0.9800	C12—H12	0.9500
C1—H1B	0.9800	C13—C14	1.394 (3)
C1—H1C	0.9800	C13—C18	1.396 (3)
C2—C3	1.543 (3)	C14—C15	1.385 (3)
C3—C4	1.521 (3)	C14—H14	0.9500
C4—C5	1.522 (3)	C15—C16	1.391 (3)
C4—H4A	0.9900	C15—H15	0.9500
C4—H4B	0.9900	C16—C17	1.380 (4)
C5—C6	1.515 (3)	C17—C18	1.392 (3)
C5—H5A	0.9900	C17—H17	0.9500
C5—H5B	0.9900	C18—H18	0.9500
C6—H6A	0.9900

C7—S1—C3	104.77 (9)	H6A—C6—H6B	107.9
C13—S2—C3	102.22 (9)	C8—C7—C12	120.11 (19)
C2—N1—C1	116.82 (18)	C8—C7—S1	118.33 (16)
C2—N1—C6	126.33 (18)	C12—C7—S1	121.44 (16)
C1—N1—C6	116.53 (18)	C7—C8—C9	120.2 (2)
N1—C1—H1A	109.5	C7—C8—H8	119.9
N1—C1—H1B	109.5	C9—C8—H8	119.9
H1A—C1—H1B	109.5	C10—C9—C8	118.7 (2)
N1—C1—H1C	109.5	C10—C9—H9	120.7
H1A—C1—H1C	109.5	C8—C9—H9	120.7
H1B—C1—H1C	109.5	C11—C10—C9	122.1 (2)
O1—C2—N1	121.9 (2)	C11—C10—Br1	118.85 (16)
O1—C2—C3	120.20 (18)	C9—C10—Br1	119.05 (17)
N1—C2—C3	117.86 (18)	C10—C11—C12	118.72 (19)
C4—C3—C2	113.70 (17)	C10—C11—H11	120.6
C4—C3—S2	111.69 (14)	C12—C11—H11	120.6
C2—C3—S2	110.22 (14)	C11—C12—C7	120.1 (2)
C4—C3—S1	114.37 (14)	C11—C12—H12	119.9
C2—C3—S1	101.59 (13)	C7—C12—H12	119.9
S2—C3—S1	104.48 (10)	C14—C13—C18	119.5 (2)
C3—C4—C5	109.99 (17)	C14—C13—S2	119.46 (17)
C3—C4—H4A	109.7	C18—C13—S2	120.96 (17)
C5—C4—H4A	109.7	C15—C14—C13	120.4 (2)
C3—C4—H4B	109.7	C15—C14—H14	119.8
C5—C4—H4B	109.7	C13—C14—H14	119.8
H4A—C4—H4B	108.2	C14—C15—C16	119.1 (2)
C6—C5—C4	108.68 (17)	C14—C15—H15	120.5
C6—C5—H5A	110.0	C16—C15—H15	120.5
C4—C5—H5A	110.0	C17—C16—C15	121.6 (2)
C6—C5—H5B	110.0	C17—C16—Br2	120.25 (18)
C4—C5—H5B	110.0	C15—C16—Br2	118.10 (18)
H5A—C5—H5B	108.3	C16—C17—C18	118.9 (2)
N1—C6—C5	112.15 (17)	C16—C17—H17	120.6
N1—C6—H6A	109.2	C18—C17—H17	120.6
C5—C6—H6A	109.2	C17—C18—C13	120.5 (2)
N1—C6—H6B	109.2	C17—C18—H18	119.7
C5—C6—H6B	109.2	C13—C18—H18	119.7

C1—N1—C2—O1	5.5 (3)	C3—S1—C7—C12	67.81 (18)
C6—N1—C2—O1	−167.7 (2)	C12—C7—C8—C9	0.4 (3)
C1—N1—C2—C3	−173.40 (18)	S1—C7—C8—C9	−175.67 (17)
C6—N1—C2—C3	13.4 (3)	C7—C8—C9—C10	−0.5 (3)
O1—C2—C3—C4	−174.26 (18)	C8—C9—C10—C11	0.0 (3)
N1—C2—C3—C4	4.6 (3)	C8—C9—C10—Br1	−179.85 (17)
O1—C2—C3—S2	−48.0 (2)	C9—C10—C11—C12	0.6 (3)
N1—C2—C3—S2	130.94 (17)	Br1—C10—C11—C12	−179.60 (15)
O1—C2—C3—S1	62.4 (2)	C10—C11—C12—C7	−0.6 (3)
N1—C2—C3—S1	−118.72 (17)	C8—C7—C12—C11	0.1 (3)
C13—S2—C3—C4	68.86 (16)	S1—C7—C12—C11	176.10 (16)
C13—S2—C3—C2	−58.56 (15)	C3—S2—C13—C14	80.85 (19)
C13—S2—C3—S1	−166.99 (10)	C3—S2—C13—C18	−103.11 (18)
C7—S1—C3—C4	30.32 (17)	C18—C13—C14—C15	0.5 (3)
C7—S1—C3—C2	153.23 (13)	S2—C13—C14—C15	176.61 (18)
C7—S1—C3—S2	−92.10 (11)	C13—C14—C15—C16	−0.5 (4)
C2—C3—C4—C5	−42.8 (2)	C14—C15—C16—C17	0.0 (4)
S2—C3—C4—C5	−168.28 (14)	C14—C15—C16—Br2	−178.26 (18)
S1—C3—C4—C5	73.31 (19)	C15—C16—C17—C18	0.5 (4)
C3—C4—C5—C6	64.5 (2)	Br2—C16—C17—C18	178.74 (17)
C2—N1—C6—C5	9.0 (3)	C16—C17—C18—C13	−0.5 (3)
C1—N1—C6—C5	−164.26 (18)	C14—C13—C18—C17	0.0 (3)
C4—C5—C6—N1	−47.3 (2)	S2—C13—C18—C17	−176.02 (17)
C3—S1—C7—C8	−116.16 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Br2ⁱ	0.95	2.87	3.744 (2)	154
C11—H11···O1ⁱⁱ	0.95	2.27	3.195 (3)	163
C1—H1B···Cg1ⁱ	0.98	2.86	3.660 (3)	139

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇Br₂NOS₂
M_r	487.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.8777 (1), 9.6481 (1), 24.6757 (3)
β (°)	93.190 (1)
V (Å³)	1872.57 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	7.61
Crystal size (mm)	0.25 × 0.25 × 0.05

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.298, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	18656, 3916, 3715
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.077, 1.10
No. of reflections	3916
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −1.26

Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Br2ⁱ	0.95	2.87	3.744 (2)	154
C11—H11···O1ⁱⁱ	0.95	2.27	3.195 (3)	163
C1—H1B···Cg1ⁱ	0.98	2.86	3.660 (3)	139

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

We thank the Brazilian agencies FAPESP, CNPq and CAPES (808/2009 to JZ-S) for financial support. CRC and BC thank CNPq for scholarships; PRO and JZ-S thank CNPq for fellowships. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

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