2-(4-Bromo-phen-yl)-5-dodec-yloxy-1,3-thia-zole.

In the structure of the title compound, C(21)H(30)BrNOS, an important inter-mediate for the preparation of liquid crystal compounds, the saturated C(12) chain shows a linear conformation while the benzene and thia-zole rings are essentially coplanar [dihedral angle = 4.5 (4)°]. The crystal packing shows no significant inter-molecular inter-actions.

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 = 424.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.248

S = 1.05

3740 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032666/zs2055Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H30BrNOS	F(000) = 888
Mr = 424.43	Dx = 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

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

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(Fo2) + (0.1139P)2] where P = (Fo2 + 2Fc2)/3
3740 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)