2-(4-Bromo­phen­yl)-5-dodec­yloxy-1,3-thia­zole

Gallardo, H.; Santos, D.M.P.O.; Bortoluzzi, A.J.

doi:10.1107/S1600536810032666

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2365

https://doi.org/10.1107/S1600536810032666

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2-(4-Bromophenyl)-5-dodecyloxy-1,3-thiazole

Hugo Gallardo,^a Deise M. P. O. Santos ^a and Adailton J. Bortoluzzi ^a ^*

^aDepartamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis, SC, Brazil
^*Correspondence e-mail: adajb@qmc.ufsc.br

(Received 28 July 2010; accepted 13 August 2010; online 21 August 2010)

In the structure of the title compound, C₂₁H₃₀BrNOS, an important intermediate for the preparation of liquid crystal compounds, the saturated C₁₂ chain shows a linear conformation while the benzene and thiazole rings are essentially coplanar [dihedral angle = 4.5 (4)°]. The crystal packing shows no significant intermolecular interactions.

Related literature

For technological applications of liquid crystals, see: Sonar et al. (2008 ); Srivastava et al. (2008 ). For liquid-crystalline compounds containing heterocyclic units, see: Cristiano et al. (2006 ); Kauhanka & Kauhanka (2006 ); Vieira et al. (2008 ). For the properties of thiazole derivatives, see: Gallardo et al. (2008 ); Yamashita (2010 ); Parra et al. (2001 ); Cohen et al. (2010 ). For the synthesis, see: Kiryanov et al. (2001 ). For related structures, see: Metzger (1984 ); Krapivin et al. (1992 ).

Experimental

Crystal data

C₂₁H₃₀BrNOS
M_r = 424.43
Monoclinic, P 2₁ /c
a = 5.507 (1) Å
b = 46.999 (6) Å
c = 8.326 (1) Å
β = 99.68 (1)°
V = 2124.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.04 mm⁻¹
T = 293 K
0.47 × 0.47 × 0.36 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan [North et al. (1968 ) and PLATON (Spek, 2009 )] T_min = 0.447, T_max = 0.527
4001 measured reflections
3740 independent reflections
1486 reflections with I > 2σ(I)
R_int = 0.101
3 standard reflections every 25 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.248
S = 1.05
3740 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810032666/zs2055sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032666/zs2055Isup2.hkl

checkCIF report

Comment top

Liquid crystals are fascinating materials with a broad range of applications. The most famous application of these materials is in liquid crystal displays (LCDs), but over the past year new applications have appeared, such as organic light emitting diodes (OLEDs) (Sonar et al., 2008; Srivastava et al., 2008). The molecular shape has a dominant influence on the existence of the liquid crystalline state. Over several years a large number of liquid-crystalline compounds containing heterocyclic units have been synthesized (Cristiano et al., 2006). Heterocycles are of great importance as core units in thermotropic liquid crystals due to their ability to impart lateral and/or longitudinal dipoles combined with changes in the molecular shape. The incorporation of heteroatoms can also result in large changes in the corresponding liquid crystalline phases and/or in the physical properties of the observed phases, because most of the heteroatoms (S, O, and N) commonly introduced are chemically classified as more polarizable than carbon (Kauhanka & Kauhanka, 2006; Vieira et al., 2008). As part of our studies of liquid crystal derivatives of thiazoles, we now report the synthesis and structure of the title compound C₂₁H₃₀BrNOS (I). In (I) (Fig. 1), the saturated C₁₂ chain shows a linear conformation while the benzene and thiazole rings are essentially coplanar [dihedral angle, 4.5 (4)°]. The crystal packing shows no significant intermolecular interactions.

Related literature top

For technological applications of liquid crystals, see: Sonar et al. (2008); Srivastava et al. (2008). For liquid-crystalline compounds containing heterocyclic units, see: Cristiano et al. (2006); Kauhanka & Kauhanka (2006); Vieira et al. (2008). For the properties of thiazole derivatives, see: Gallardo et al. (2008); Yamashita (2010); Parra et al. (2001); Cohen et al. (2010). For the synthesis, see: Kiryanov et al. (2001). For related structures, see Katrinsky & Metzger (1984); Krapivin et al. (1992).

Experimental top

Dodecyl-2-(4-bromobenzamido)acetate (4.26 g, 10 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent) (8.10 g, 20 mmol) was mixed with dry toluene (150 ml) and heated under reflux for 6 h. The crude product was separated by column chromatography (dichloromethane) and after evaporation of the solvent the solid was recrystallized from methanol to afford the title compound as a white solid (3.8 g, 95%): ¹H NMR (CDCl₃) = 7.64 (d, J = 8.0 Hz, 2H), 7.48 (d, J = 8.0 Hz, 2H), 7.06 (s, 1H), 4.03 (t, J = 6.5 Hz, 2H), 1.81 (q, J = 7.0 Hz, 2H), 1.52–1.20 (m, 18H), 0.89 (t, J = 6.8 Hz, 3H); Elemental analysis for C₂₁H₃₀BrNOS: calc.: C 59.43; H 7.12; N 3.30; S 7.55%. Found: C 59.42; H 7.16; N 3.43; S 8.25%.

Structure description top

For technological applications of liquid crystals, see: Sonar et al. (2008); Srivastava et al. (2008). For liquid-crystalline compounds containing heterocyclic units, see: Cristiano et al. (2006); Kauhanka & Kauhanka (2006); Vieira et al. (2008). For the properties of thiazole derivatives, see: Gallardo et al. (2008); Yamashita (2010); Parra et al. (2001); Cohen et al. (2010). For the synthesis, see: Kiryanov et al. (2001). For related structures, see Katrinsky & Metzger (1984); Krapivin et al. (1992).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: SET4 in CAD-4 Software (Enraf–Nonius, 1989); data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with atom labelling scheme. Displacement ellipsoids are shown at the 40% probability level.

2-(4-Bromophenyl)-5-dodecyloxy-1,3-thiazole top

Crystal data top

C₂₁H₃₀BrNOS	F(000) = 888
M_r = 424.43	D_x = 1.327 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.507 (1) Å	θ = 3.8–11.5°
b = 46.999 (6) Å	µ = 2.04 mm⁻¹
c = 8.326 (1) Å	T = 293 K
β = 99.68 (1)°	Block, colorless
V = 2124.3 (5) Å³	0.47 × 0.47 × 0.36 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1486 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.101
Graphite monochromator	θ_max = 25.0°, θ_min = 0.9°
ω–2θ scans	h = −6→6
Absorption correction: ψ scan [North et al. (1968) and PLATON (Spek, 2009)]	k = −55→0
T_min = 0.447, T_max = 0.527	l = −9→0
4001 measured reflections	3 standard reflections every 25 reflections
3740 independent reflections	intensity decay: 1%

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.248	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1139P)²] where P = (F_o² + 2F_c²)/3
3740 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₁H₃₀BrNOS	V = 2124.3 (5) Å³
M_r = 424.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.507 (1) Å	µ = 2.04 mm⁻¹
b = 46.999 (6) Å	T = 293 K
c = 8.326 (1) Å	0.47 × 0.47 × 0.36 mm
β = 99.68 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1486 reflections with I > 2σ(I)
Absorption correction: ψ scan [North et al. (1968) and PLATON (Spek, 2009)]	R_int = 0.101
T_min = 0.447, T_max = 0.527	3 standard reflections every 25 reflections
4001 measured reflections	intensity decay: 1%
3740 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.248	H-atom parameters constrained
S = 1.05	Δρ_max = 0.61 e Å⁻³
3740 reflections	Δρ_min = −0.47 e Å⁻³
227 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.4151 (15)	0.5923 (2)	−0.0151 (9)	0.045 (2)
C2	−0.6447 (17)	0.5928 (2)	−0.1107 (10)	0.055 (2)
H2	−0.7290	0.5758	−0.1357	0.067*
C3	−0.7521 (17)	0.6180 (2)	−0.1703 (11)	0.064 (3)
H3	−0.9067	0.6177	−0.2356	0.077*
C4	−0.6371 (19)	0.6430 (2)	−0.1357 (11)	0.059 (3)
C5	−0.4059 (19)	0.6436 (2)	−0.0409 (12)	0.067 (3)
H5	−0.3244	0.6609	−0.0184	0.081*
C6	−0.2960 (16)	0.6186 (2)	0.0206 (10)	0.057 (2)
H6	−0.1417	0.6191	0.0862	0.068*
C7	−0.3088 (14)	0.5663 (2)	0.0520 (9)	0.050 (2)
C8	−0.0587 (16)	0.52788 (19)	0.1924 (10)	0.051 (2)
C9	−0.2786 (16)	0.51987 (19)	0.1131 (11)	0.057 (3)
H9	−0.3338	0.5012	0.1129	0.069*
C10	0.0700 (15)	0.48362 (19)	0.2965 (10)	0.053 (2)
H10A	0.0349	0.4753	0.1885	0.063*
H10B	−0.0741	0.4812	0.3480	0.063*
C11	0.2887 (16)	0.46862 (19)	0.3963 (11)	0.056 (2)
H11A	0.4332	0.4714	0.3456	0.067*
H11B	0.3222	0.4768	0.5046	0.067*
C12	0.2390 (14)	0.43752 (19)	0.4087 (10)	0.051 (2)
H12A	0.2078	0.4295	0.2999	0.061*
H12B	0.0913	0.4350	0.4562	0.061*
C13	0.4524 (15)	0.42099 (19)	0.5121 (11)	0.054 (2)
H13A	0.6000	0.4237	0.4647	0.065*
H13B	0.4828	0.4291	0.6207	0.065*
C14	0.4093 (14)	0.3900 (2)	0.5259 (11)	0.060 (3)
H14A	0.3704	0.3821	0.4172	0.072*
H14B	0.2670	0.3873	0.5788	0.072*
C15	0.6280 (16)	0.37363 (19)	0.6215 (11)	0.057 (2)
H15A	0.7714	0.3774	0.5713	0.069*
H15B	0.6618	0.3813	0.7311	0.069*
C16	0.6002 (16)	0.3421 (2)	0.6340 (11)	0.059 (3)
H16A	0.5517	0.3343	0.5253	0.071*
H16B	0.4686	0.3381	0.6949	0.071*
C17	0.8306 (16)	0.32698 (18)	0.7151 (12)	0.063 (3)
H17A	0.9627	0.3315	0.6555	0.075*
H17B	0.8767	0.3346	0.8244	0.075*
C18	0.8118 (16)	0.2954 (2)	0.7266 (11)	0.068 (3)
H18A	0.7613	0.2877	0.6180	0.082*
H18B	0.6848	0.2908	0.7901	0.082*
C19	1.0484 (16)	0.28141 (19)	0.8031 (11)	0.066 (3)
H19A	1.0943	0.2886	0.9133	0.079*
H19B	1.1768	0.2870	0.7427	0.079*
C20	1.0392 (17)	0.2490 (2)	0.8096 (13)	0.071 (3)
H20A	0.9186	0.2435	0.8761	0.086*
H20B	0.9829	0.2419	0.7003	0.086*
C21	1.2787 (18)	0.2351 (2)	0.8758 (17)	0.104 (4)
H21A	1.3474	0.2438	0.9777	0.156*
H21B	1.3906	0.2374	0.7999	0.156*
H21C	1.2521	0.2152	0.8923	0.156*
N1	−0.4170 (14)	0.54122 (16)	0.0321 (9)	0.061 (2)
O1	0.1218 (10)	0.51313 (14)	0.2839 (7)	0.0612 (17)
S1	−0.0169 (4)	0.56399 (5)	0.1715 (3)	0.0572 (7)
Br1	−0.7883 (2)	0.67797 (3)	−0.20868 (16)	0.0951 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.037 (5)	0.061 (7)	0.033 (5)	−0.002 (5)	0.000 (4)	0.001 (4)
C2	0.061 (6)	0.053 (7)	0.055 (6)	−0.012 (5)	0.014 (5)	0.007 (5)
C3	0.048 (6)	0.071 (8)	0.071 (7)	0.001 (6)	0.001 (5)	−0.002 (6)
C4	0.067 (7)	0.063 (7)	0.048 (6)	0.013 (6)	0.017 (5)	0.005 (5)
C5	0.071 (7)	0.047 (7)	0.083 (7)	0.002 (5)	0.011 (6)	−0.007 (5)
C6	0.046 (5)	0.048 (6)	0.072 (7)	0.002 (5)	−0.002 (5)	0.005 (5)
C7	0.037 (5)	0.074 (7)	0.034 (5)	0.007 (5)	−0.006 (4)	0.012 (5)
C8	0.045 (5)	0.047 (6)	0.054 (6)	−0.001 (5)	−0.017 (5)	0.002 (5)
C9	0.059 (6)	0.036 (6)	0.068 (6)	0.000 (5)	−0.016 (5)	0.017 (5)
C10	0.053 (6)	0.045 (6)	0.056 (6)	−0.003 (5)	−0.001 (5)	0.013 (5)
C11	0.059 (6)	0.053 (7)	0.056 (6)	0.013 (5)	0.008 (5)	0.004 (5)
C12	0.043 (5)	0.056 (6)	0.051 (6)	0.006 (5)	0.000 (4)	0.002 (5)
C13	0.049 (6)	0.056 (7)	0.054 (6)	0.001 (5)	0.002 (5)	0.007 (5)
C14	0.031 (5)	0.079 (8)	0.066 (6)	−0.012 (5)	−0.005 (5)	0.003 (5)
C15	0.051 (6)	0.048 (7)	0.071 (6)	0.011 (5)	0.003 (5)	0.009 (5)
C16	0.046 (6)	0.076 (8)	0.054 (6)	0.015 (5)	0.006 (5)	0.006 (5)
C17	0.051 (6)	0.053 (7)	0.082 (7)	0.006 (5)	0.003 (5)	0.013 (5)
C18	0.057 (6)	0.058 (7)	0.081 (7)	0.005 (5)	−0.010 (5)	0.004 (6)
C19	0.061 (6)	0.047 (7)	0.085 (7)	−0.001 (5)	−0.003 (5)	0.003 (5)
C20	0.070 (7)	0.050 (7)	0.090 (8)	−0.005 (5)	0.002 (6)	0.016 (6)
C21	0.074 (8)	0.054 (8)	0.171 (12)	0.015 (6)	−0.017 (8)	0.031 (8)
N1	0.060 (5)	0.037 (5)	0.079 (6)	−0.016 (4)	−0.010 (4)	0.003 (4)
O1	0.050 (4)	0.058 (5)	0.069 (4)	−0.012 (3)	−0.010 (3)	0.009 (3)
S1	0.0479 (13)	0.0455 (15)	0.0700 (16)	−0.0069 (12)	−0.0138 (12)	0.0077 (12)
Br1	0.1110 (11)	0.0733 (9)	0.1017 (10)	0.0372 (7)	0.0199 (7)	0.0262 (7)

Geometric parameters (Å, º) top

C1—C2	1.376 (11)	C12—H12B	0.9700
C1—C6	1.407 (12)	C13—C14	1.481 (12)
C1—C7	1.428 (12)	C13—H13A	0.9700
C2—C3	1.381 (12)	C13—H13B	0.9700
C2—H2	0.9300	C14—C15	1.535 (11)
C3—C4	1.343 (13)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.381 (13)	C15—C16	1.497 (12)
C4—Br1	1.895 (9)	C15—H15A	0.9700
C5—C6	1.383 (12)	C15—H15B	0.9700
C5—H5	0.9300	C16—C17	1.510 (11)
C6—H6	0.9300	C16—H16A	0.9700
C7—N1	1.317 (11)	C16—H16B	0.9700
C7—S1	1.746 (8)	C17—C18	1.490 (12)
C8—C9	1.332 (11)	C17—H17A	0.9700
C8—O1	1.339 (9)	C17—H17B	0.9700
C8—S1	1.725 (9)	C18—C19	1.503 (11)
C9—N1	1.367 (10)	C18—H18A	0.9700
C9—H9	0.9300	C18—H18B	0.9700
C10—O1	1.423 (10)	C19—C20	1.525 (12)
C10—C11	1.517 (11)	C19—H19A	0.9700
C10—H10A	0.9700	C19—H19B	0.9700
C10—H10B	0.9700	C20—C21	1.492 (12)
C11—C12	1.494 (12)	C20—H20A	0.9700
C11—H11A	0.9700	C20—H20B	0.9700
C11—H11B	0.9700	C21—H21A	0.9600
C12—C13	1.544 (11)	C21—H21B	0.9600
C12—H12A	0.9700	C21—H21C	0.9600

C2—C1—C6	117.2 (8)	C13—C14—C15	114.3 (7)
C2—C1—C7	121.1 (8)	C13—C14—H14A	108.7
C6—C1—C7	121.6 (8)	C15—C14—H14A	108.7
C1—C2—C3	121.2 (9)	C13—C14—H14B	108.7
C1—C2—H2	119.4	C15—C14—H14B	108.7
C3—C2—H2	119.4	H14A—C14—H14B	107.6
C4—C3—C2	121.1 (9)	C16—C15—C14	117.0 (8)
C4—C3—H3	119.4	C16—C15—H15A	108.1
C2—C3—H3	119.4	C14—C15—H15A	108.1
C3—C4—C5	119.8 (9)	C16—C15—H15B	108.1
C3—C4—Br1	121.6 (8)	C14—C15—H15B	108.1
C5—C4—Br1	118.6 (8)	H15A—C15—H15B	107.3
C4—C5—C6	119.8 (9)	C15—C16—C17	114.1 (8)
C4—C5—H5	120.1	C15—C16—H16A	108.7
C6—C5—H5	120.1	C17—C16—H16A	108.7
C5—C6—C1	120.7 (8)	C15—C16—H16B	108.7
C5—C6—H6	119.6	C17—C16—H16B	108.7
C1—C6—H6	119.6	H16A—C16—H16B	107.6
N1—C7—C1	124.7 (7)	C18—C17—C16	115.7 (8)
N1—C7—S1	111.8 (7)	C18—C17—H17A	108.4
C1—C7—S1	123.6 (7)	C16—C17—H17A	108.4
C9—C8—O1	131.4 (9)	C18—C17—H17B	108.4
C9—C8—S1	110.7 (7)	C16—C17—H17B	108.4
O1—C8—S1	117.9 (6)	H17A—C17—H17B	107.4
C8—C9—N1	115.0 (8)	C17—C18—C19	113.5 (8)
C8—C9—H9	122.5	C17—C18—H18A	108.9
N1—C9—H9	122.5	C19—C18—H18A	108.9
O1—C10—C11	110.1 (7)	C17—C18—H18B	108.9
O1—C10—H10A	109.7	C19—C18—H18B	108.9
C11—C10—H10A	109.7	H18A—C18—H18B	107.7
O1—C10—H10B	109.6	C18—C19—C20	114.9 (8)
C11—C10—H10B	109.7	C18—C19—H19A	108.5
H10A—C10—H10B	108.2	C20—C19—H19A	108.5
C12—C11—C10	110.8 (7)	C18—C19—H19B	108.5
C12—C11—H11A	109.5	C20—C19—H19B	108.5
C10—C11—H11A	109.5	H19A—C19—H19B	107.5
C12—C11—H11B	109.5	C21—C20—C19	114.7 (8)
C10—C11—H11B	109.5	C21—C20—H20A	108.6
H11A—C11—H11B	108.1	C19—C20—H20A	108.6
C11—C12—C13	113.6 (7)	C21—C20—H20B	108.6
C11—C12—H12A	108.9	C19—C20—H20B	108.6
C13—C12—H12A	108.9	H20A—C20—H20B	107.6
C11—C12—H12B	108.9	C20—C21—H21A	109.5
C13—C12—H12B	108.9	C20—C21—H21B	109.5
H12A—C12—H12B	107.7	H21A—C21—H21B	109.5
C14—C13—C12	114.9 (7)	C20—C21—H21C	109.5
C14—C13—H13A	108.5	H21A—C21—H21C	109.5
C12—C13—H13A	108.5	H21B—C21—H21C	109.5
C14—C13—H13B	108.5	C7—N1—C9	113.0 (7)
C12—C13—H13B	108.5	C8—O1—C10	114.0 (6)
H13A—C13—H13B	107.5	C8—S1—C7	89.5 (4)

C6—C1—C2—C3	0.6 (13)	C11—C12—C13—C14	−179.7 (8)
C7—C1—C2—C3	177.3 (8)	C12—C13—C14—C15	177.0 (7)
C1—C2—C3—C4	−0.6 (14)	C13—C14—C15—C16	−177.5 (8)
C2—C3—C4—C5	0.9 (14)	C14—C15—C16—C17	174.3 (8)
C2—C3—C4—Br1	−177.2 (7)	C15—C16—C17—C18	−178.7 (9)
C3—C4—C5—C6	−1.3 (14)	C16—C17—C18—C19	178.0 (8)
Br1—C4—C5—C6	176.9 (7)	C17—C18—C19—C20	−177.2 (9)
C4—C5—C6—C1	1.3 (14)	C18—C19—C20—C21	176.3 (9)
C2—C1—C6—C5	−0.9 (13)	C1—C7—N1—C9	−178.2 (8)
C7—C1—C6—C5	−177.6 (8)	S1—C7—N1—C9	1.8 (10)
C2—C1—C7—N1	−1.1 (13)	C8—C9—N1—C7	−2.0 (12)
C6—C1—C7—N1	175.5 (8)	C9—C8—O1—C10	1.0 (13)
C2—C1—C7—S1	178.9 (6)	S1—C8—O1—C10	179.1 (6)
C6—C1—C7—S1	−4.5 (12)	C11—C10—O1—C8	177.7 (7)
O1—C8—C9—N1	179.5 (9)	C9—C8—S1—C7	−0.2 (7)
S1—C8—C9—N1	1.2 (11)	O1—C8—S1—C7	−178.7 (7)
O1—C10—C11—C12	−179.2 (7)	N1—C7—S1—C8	−0.9 (7)
C10—C11—C12—C13	−178.7 (7)	C1—C7—S1—C8	179.0 (7)

Experimental details

Crystal data
Chemical formula	C₂₁H₃₀BrNOS
M_r	424.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.507 (1), 46.999 (6), 8.326 (1)
β (°)	99.68 (1)
V (Å³)	2124.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.04
Crystal size (mm)	0.47 × 0.47 × 0.36

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan [North et al. (1968) and PLATON (Spek, 2009)]
T_min, T_max	0.447, 0.527
No. of measured, independent and observed [I > 2σ(I)] reflections	4001, 3740, 1486
R_int	0.101
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.248, 1.05
No. of reflections	3740
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.47

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), SET4 in CAD-4 Software (Enraf–Nonius, 1989), HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Acknowledgements

The authors thank the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and the Instituto Nacional de Ciência e Tecnologia (INCT) - Catálize for financial assistance.

References

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