5-[(4-Bromo­benz­yl)­oxy]-4-(4-methyl­benzene­sulfon­yl)-1,3-thia­zole

In the title compound, C₁₇H₁₄BrNO₃S₂, the mean plane of the thia­zole ring subtends dihedral angles of 3.6 (2) and 79.9 (2)° with the bromo­benzyl and toluyl rings, respectively. In the crystal, short S...O contacts [3.012 (3) Å] and aromatic π–π stacking between the thia­zole and toluyl rings [centroid–centroid separation = 3.687 (2) Å] are observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.056
• wR factor = 0.144
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.16 Do !
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        O16 Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0062 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C17 H14 Br N O3 S2
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.407 Check

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.005 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

5-[(4-Bromobenzyl)oxy]-4-(4-methylbenzenesulfonyl)-1,3-thiazole

Crystal data

C17H14BrNO3S2	Z = 2
Mr = 424.31	F(000) = 428
Triclinic, P1	Dx = 1.632 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6092 (4) Å	Cell parameters from 3955 reflections
b = 8.2768 (5) Å	θ = 2.5–27.5°
c = 13.8718 (8) Å	µ = 2.64 mm^−1
α = 95.175 (5)°	T = 293 K
β = 94.559 (5)°	Block, pale yellow
γ = 94.814 (5)°	0.28 × 0.25 × 0.22 mm
V = 863.67 (9) Å^3

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.035
Detector resolution: 18.4 pixels mm^-1	θmax = 27.5°, θmin = 2.5°
ω and φ scans	h = −9→9
7351 measured reflections	k = −10→8
3955 independent reflections	l = −16→18
2633 reflections with I > 2σ(I)

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.144	w = 1/[Σ^2(FO^2) + (0.0501P)^2 + 0.4404P] where P = (FO^2 + 2FC^2)/3
S = 1.04	(Δ/σ)max = 0.003
3955 reflections	Δρmax = 0.35 e Å^−3
218 parameters	Δρmin = −0.67 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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.

The H atoms were positioned geometrically and allowed to ride on their parent atom, with C–H distance in the range of 0.93 to 0.97 Å; U_iso(H) = 1.2–1.5U_eq (carrier atom) for all H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br24	0.46321 (8)	0.97111 (7)	0.79555 (4)	0.0674 (2)
S8	0.12112 (14)	0.52364 (12)	1.29198 (8)	0.0382 (3)
S14	−0.39923 (15)	0.56970 (15)	1.16549 (9)	0.0508 (4)
O9	0.2178 (4)	0.5355 (4)	1.2075 (2)	0.0474 (10)
O10	0.1418 (4)	0.3884 (3)	1.3483 (2)	0.0516 (11)
O16	−0.0708 (5)	0.6623 (5)	1.1124 (3)	0.0779 (14)
N12	−0.2288 (5)	0.4619 (4)	1.3100 (3)	0.0450 (12)
C1	0.2819 (7)	1.1548 (6)	1.5513 (4)	0.0647 (19)
C2	0.2422 (6)	0.9961 (5)	1.4872 (3)	0.0458 (16)
C3	0.2264 (6)	0.9965 (5)	1.3866 (3)	0.0483 (16)
C4	0.1911 (6)	0.8518 (5)	1.3277 (3)	0.0445 (16)
C5	0.1718 (5)	0.7057 (5)	1.3686 (3)	0.0358 (12)
C6	0.1858 (6)	0.7040 (5)	1.4683 (3)	0.0458 (14)
C7	0.2221 (7)	0.8489 (6)	1.5267 (3)	0.0539 (16)
C11	−0.1060 (5)	0.5239 (5)	1.2538 (3)	0.0366 (12)
C13	−0.3864 (6)	0.4786 (6)	1.2722 (3)	0.0504 (17)
C15	−0.1693 (6)	0.5886 (5)	1.1725 (3)	0.0438 (14)
C17	−0.1435 (6)	0.7034 (6)	1.0217 (3)	0.0471 (16)
C18	0.0056 (6)	0.7718 (5)	0.9690 (3)	0.0393 (14)
C19	0.1812 (6)	0.7713 (5)	1.0047 (3)	0.0449 (14)
C20	0.3145 (6)	0.8305 (5)	0.9536 (3)	0.0490 (17)
C21	0.2766 (6)	0.8919 (5)	0.8658 (3)	0.0452 (14)
C22	0.1037 (7)	0.8947 (5)	0.8301 (3)	0.0496 (16)
C23	−0.0312 (6)	0.8358 (5)	0.8813 (3)	0.0473 (17)
H1A	0.20336	1.15773	1.60218	0.0970*
H1B	0.26522	1.24432	1.51311	0.0970*
H1C	0.40214	1.16313	1.57933	0.0970*
H3	0.23960	1.09451	1.35890	0.0580*
H4	0.18030	0.85259	1.26051	0.0540*
H6	0.17101	0.60604	1.49586	0.0550*
H7	0.23317	0.84745	1.59382	0.0650*
H13	−0.48714	0.44345	1.30113	0.0610*
H16A	−0.22813	0.78345	1.03150	0.0560*
H16B	−0.20413	0.60745	0.98417	0.0560*
H18	0.20832	0.73038	1.06380	0.0540*
H19	0.43168	0.82933	0.97807	0.0590*
H21	0.07767	0.93653	0.77112	0.0600*
H22	−0.14821	0.83882	0.85688	0.0570*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br24	0.0677 (4)	0.0740 (4)	0.0582 (4)	−0.0139 (3)	0.0067 (3)	0.0127 (3)
S8	0.0301 (5)	0.0405 (5)	0.0433 (6)	0.0046 (4)	−0.0011 (4)	0.0023 (5)
S14	0.0309 (6)	0.0608 (7)	0.0595 (8)	0.0038 (5)	−0.0024 (5)	0.0055 (6)
O9	0.0313 (17)	0.0651 (19)	0.0448 (17)	0.0062 (15)	0.0058 (13)	−0.0036 (15)
O10	0.051 (2)	0.0425 (16)	0.061 (2)	0.0102 (15)	−0.0057 (16)	0.0080 (15)
O16	0.038 (2)	0.134 (3)	0.065 (2)	−0.007 (2)	−0.0069 (17)	0.052 (2)
N12	0.037 (2)	0.051 (2)	0.047 (2)	0.0018 (17)	0.0046 (17)	0.0055 (17)
C1	0.068 (4)	0.058 (3)	0.064 (3)	0.011 (3)	−0.006 (3)	−0.011 (3)
C2	0.038 (3)	0.044 (2)	0.053 (3)	0.007 (2)	−0.002 (2)	−0.006 (2)
C3	0.058 (3)	0.038 (2)	0.049 (3)	0.001 (2)	0.003 (2)	0.009 (2)
C4	0.046 (3)	0.052 (3)	0.036 (2)	0.002 (2)	0.0059 (19)	0.008 (2)
C5	0.029 (2)	0.040 (2)	0.038 (2)	0.0019 (17)	−0.0013 (17)	0.0069 (18)
C6	0.049 (3)	0.048 (2)	0.040 (2)	0.000 (2)	0.000 (2)	0.010 (2)
C7	0.065 (3)	0.061 (3)	0.034 (2)	0.005 (3)	−0.005 (2)	0.004 (2)
C11	0.033 (2)	0.037 (2)	0.039 (2)	0.0032 (18)	0.0028 (18)	0.0004 (17)
C13	0.037 (3)	0.058 (3)	0.056 (3)	0.000 (2)	0.012 (2)	0.001 (2)
C15	0.034 (2)	0.048 (2)	0.048 (3)	−0.002 (2)	0.001 (2)	0.004 (2)
C17	0.040 (3)	0.059 (3)	0.041 (2)	0.007 (2)	−0.005 (2)	0.003 (2)
C18	0.044 (3)	0.038 (2)	0.035 (2)	0.0059 (19)	−0.0009 (18)	0.0012 (18)
C19	0.045 (3)	0.050 (2)	0.038 (2)	0.001 (2)	−0.004 (2)	0.005 (2)
C20	0.041 (3)	0.055 (3)	0.048 (3)	−0.001 (2)	−0.007 (2)	0.004 (2)
C21	0.048 (3)	0.044 (2)	0.041 (2)	0.000 (2)	0.000 (2)	−0.003 (2)
C22	0.059 (3)	0.050 (2)	0.039 (3)	0.005 (2)	−0.005 (2)	0.008 (2)
C23	0.042 (3)	0.054 (3)	0.045 (3)	0.009 (2)	−0.006 (2)	0.004 (2)

Geometric parameters (Å, º)

Br24—C21	1.891 (4)	C18—C19	1.388 (6)
S8—O9	1.439 (3)	C18—C23	1.388 (6)
S8—O10	1.434 (3)	C19—C20	1.366 (6)
S8—C5	1.760 (4)	C20—C21	1.380 (6)
S8—C11	1.767 (4)	C21—C22	1.371 (7)
S14—C13	1.721 (5)	C22—C23	1.375 (7)
S14—C15	1.738 (5)	C1—H1A	0.9600
O16—C15	1.320 (6)	C1—H1B	0.9600
O16—C17	1.415 (6)	C1—H1C	0.9600
N12—C11	1.361 (6)	C3—H3	0.9300
N12—C13	1.294 (6)	C4—H4	0.9300
C1—C2	1.512 (7)	C6—H6	0.9300
C2—C3	1.391 (6)	C7—H7	0.9300
C2—C7	1.382 (6)	C13—H13	0.9300
C3—C4	1.382 (6)	C17—H16A	0.9700
C4—C5	1.383 (6)	C17—H16B	0.9700
C5—C6	1.380 (6)	C19—H18	0.9300
C6—C7	1.380 (6)	C20—H19	0.9300
C11—C15	1.363 (6)	C22—H21	0.9300
C17—C18	1.497 (6)	C23—H22	0.9300
O9—S8—O10	118.94 (19)	Br24—C21—C22	120.5 (3)
O9—S8—C5	108.10 (19)	C20—C21—C22	119.7 (4)
O9—S8—C11	107.43 (19)	C21—C22—C23	120.1 (4)
O10—S8—C5	108.85 (18)	C18—C23—C22	120.6 (4)
O10—S8—C11	108.17 (19)	C2—C1—H1A	109.00
C5—S8—C11	104.40 (19)	C2—C1—H1B	109.00
C13—S14—C15	88.4 (2)	C2—C1—H1C	110.00
C15—O16—C17	121.7 (4)	H1A—C1—H1B	109.00
C11—N12—C13	110.0 (4)	H1A—C1—H1C	109.00
C1—C2—C3	120.0 (4)	H1B—C1—H1C	109.00
C1—C2—C7	121.1 (4)	C2—C3—H3	120.00
C3—C2—C7	118.8 (4)	C4—C3—H3	120.00
C2—C3—C4	120.3 (4)	C3—C4—H4	120.00
C3—C4—C5	120.1 (4)	C5—C4—H4	120.00
S8—C5—C4	119.1 (3)	C5—C6—H6	120.00
S8—C5—C6	120.7 (3)	C7—C6—H6	120.00
C4—C5—C6	120.2 (4)	C2—C7—H7	119.00
C5—C6—C7	119.5 (4)	C6—C7—H7	119.00
C2—C7—C6	121.2 (4)	S14—C13—H13	122.00
S8—C11—N12	119.1 (3)	N12—C13—H13	122.00
S8—C11—C15	124.4 (3)	O16—C17—H16A	110.00
N12—C11—C15	116.5 (4)	O16—C17—H16B	110.00
S14—C13—N12	116.2 (3)	C18—C17—H16A	110.00
S14—C15—O16	125.8 (3)	C18—C17—H16B	110.00
S14—C15—C11	109.0 (3)	H16A—C17—H16B	108.00
O16—C15—C11	125.1 (4)	C18—C19—H18	120.00
O16—C17—C18	107.8 (4)	C20—C19—H18	120.00
C17—C18—C19	121.8 (4)	C19—C20—H19	120.00
C17—C18—C23	119.6 (4)	C21—C20—H19	120.00
C19—C18—C23	118.6 (4)	C21—C22—H21	120.00
C18—C19—C20	120.5 (4)	C23—C22—H21	120.00
C19—C20—C21	120.5 (4)	C18—C23—H22	120.00
Br24—C21—C20	119.8 (3)	C22—C23—H22	120.00
O9—S8—C5—C4	38.3 (4)	C3—C2—C7—C6	−0.4 (7)
O9—S8—C5—C6	−144.0 (3)	C2—C3—C4—C5	−0.2 (7)
O10—S8—C5—C4	168.8 (3)	C3—C4—C5—S8	178.3 (3)
O10—S8—C5—C6	−13.5 (4)	C3—C4—C5—C6	0.7 (7)
C11—S8—C5—C4	−75.8 (4)	S8—C5—C6—C7	−178.7 (4)
C11—S8—C5—C6	101.8 (4)	C4—C5—C6—C7	−1.1 (7)
O9—S8—C11—N12	158.7 (3)	C5—C6—C7—C2	1.0 (7)
O9—S8—C11—C15	−24.0 (4)	S8—C11—C15—S14	−177.6 (2)
O10—S8—C11—N12	29.2 (4)	S8—C11—C15—O16	−1.4 (7)
O10—S8—C11—C15	−153.6 (4)	N12—C11—C15—S14	−0.3 (5)
C5—S8—C11—N12	−86.7 (4)	N12—C11—C15—O16	176.0 (4)
C5—S8—C11—C15	90.6 (4)	O16—C17—C18—C19	6.7 (6)
C15—S14—C13—N12	−0.4 (4)	O16—C17—C18—C23	−174.2 (4)
C13—S14—C15—O16	−175.9 (4)	C17—C18—C19—C20	178.2 (4)
C13—S14—C15—C11	0.4 (3)	C23—C18—C19—C20	−1.0 (6)
C17—O16—C15—S14	−14.6 (6)	C17—C18—C23—C22	−178.0 (4)
C17—O16—C15—C11	169.8 (4)	C19—C18—C23—C22	1.2 (6)
C15—O16—C17—C18	−175.3 (4)	C18—C19—C20—C21	0.1 (6)
C13—N12—C11—S8	177.5 (3)	C19—C20—C21—Br24	−179.3 (3)
C13—N12—C11—C15	0.0 (5)	C19—C20—C21—C22	0.6 (6)
C11—N12—C13—S14	0.3 (5)	Br24—C21—C22—C23	179.5 (3)
C1—C2—C3—C4	179.7 (4)	C20—C21—C22—C23	−0.4 (6)
C7—C2—C3—C4	0.0 (7)	C21—C22—C23—C18	−0.5 (6)
C1—C2—C7—C6	180.0 (5)