5-(4-Methoxy­phenyl)-4-methyl-2-thio­xo-2,3-di­hydro-1,3-thia­zol-3-yl benzoate at 100 K

A Z arrangement of substituents about the carboxyl­ate C-O bond causes a syn positioning of the carbonyl O atom and the heterocyclic part of the title compound, C₁₈H₁₅NO₃S. The carboxyl­ate entity is inclined by -28.1 (3)° to the phenyl group. The planes of the thia­zol-2(3H)-thione subunit and the carboxyl­ate group are orthogonally arranged.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.090
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S2     -   C2      ..       5.37 su
PLAT351_ALERT_3_C Long    C-H Bond (0.96A)   C11    -   H11    ...       1.11 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON2003 (Spek, 1990, 2003) and ORTEP-3 (Farrugia, 1997, 2005); software used to prepare material for publication: SHELXL97.

5-(4-Methoxyphenyl)-4-methyl-2-thioxo-2,3-dihydro-1,3-thiazol-3-yl benzoate

Crystal data

C18H15NO3S2	F(000) = 744
Mr = 357.43	Dx = 1.421 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.3037 (5) Å	Cell parameters from 2804 reflections
b = 15.287 (1) Å	θ = 2.8–24.0°
c = 14.985 (1) Å	µ = 0.33 mm^−1
β = 92.735 (7)°	T = 100 K
V = 1671.19 (19) Å^3	Prism, light brown
Z = 4	0.36 × 0.14 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur (TM) diffractometer with a Sapphire CCD detector	2885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 26.4°, θmin = 4.1°
Rotation method data acquisition using ω scans	h = −9→6
10562 measured reflections	k = −19→19
3376 independent reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: difference Fourier map
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0392P)^2 + 0.8411P] where P = (Fo^2 + 2Fc^2)/3
3376 reflections	(Δ/σ)max = 0.011
262 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
C2	0.4594 (2)	0.57030 (12)	0.62253 (12)	0.0197 (4)
C4	0.7214 (2)	0.63432 (12)	0.55991 (12)	0.0175 (4)
C5	0.6186 (2)	0.70688 (12)	0.56984 (11)	0.0173 (4)
C6	0.9108 (3)	0.62490 (13)	0.52892 (14)	0.0219 (4)
H6A	0.989 (3)	0.6002 (14)	0.5724 (15)	0.026*
H6B	0.958 (3)	0.6820 (15)	0.5147 (14)	0.026*
H6C	0.907 (3)	0.5871 (14)	0.4749 (15)	0.026*
C7	0.6587 (2)	0.79878 (12)	0.54927 (12)	0.0170 (4)
C8	0.7180 (2)	0.82399 (12)	0.46591 (12)	0.0193 (4)
H8	0.734 (3)	0.7791 (14)	0.4198 (14)	0.023*
C9	0.7528 (2)	0.91125 (12)	0.44665 (13)	0.0197 (4)
H9	0.794 (3)	0.9269 (14)	0.3907 (14)	0.024*
C10	0.7283 (2)	0.97448 (12)	0.51130 (12)	0.0176 (4)
C11	0.6682 (2)	0.95065 (12)	0.59506 (12)	0.0191 (4)
H11	0.643 (3)	1.0007 (13)	0.6465 (14)	0.023*
C12	0.6339 (2)	0.86376 (12)	0.61321 (12)	0.0178 (4)
H12	0.594 (3)	0.8485 (14)	0.6708 (14)	0.021*
C13	0.8255 (3)	1.09062 (13)	0.41788 (14)	0.0232 (4)
H13A	0.734 (3)	1.0797 (14)	0.3702 (15)	0.028*
H13B	0.850 (3)	1.1518 (16)	0.4263 (14)	0.028*
H13C	0.941 (3)	1.0627 (14)	0.4035 (14)	0.028*
C14	0.7956 (2)	0.45820 (12)	0.67019 (12)	0.0174 (4)
C15	0.8298 (2)	0.36317 (12)	0.67610 (12)	0.0180 (4)
C16	0.9816 (3)	0.33409 (13)	0.72842 (12)	0.0208 (4)
H16	1.061 (3)	0.3759 (14)	0.7587 (14)	0.025*
C17	1.0138 (3)	0.24510 (13)	0.73770 (13)	0.0221 (4)
H17	1.115 (3)	0.2268 (14)	0.7737 (14)	0.027*
C18	0.8941 (3)	0.18541 (13)	0.69555 (13)	0.0234 (4)
H18	0.913 (3)	0.1256 (16)	0.7039 (14)	0.028*
C19	0.7427 (3)	0.21465 (13)	0.64422 (13)	0.0246 (4)
H19	0.661 (3)	0.1751 (15)	0.6142 (15)	0.029*
C20	0.7105 (3)	0.30319 (13)	0.63364 (12)	0.0211 (4)
H20	0.608 (3)	0.3250 (14)	0.5977 (15)	0.025*
N3	0.6269 (2)	0.56077 (10)	0.58826 (10)	0.0176 (3)
O1	0.70484 (17)	0.47792 (8)	0.58709 (8)	0.0188 (3)
O2	0.83525 (18)	0.51379 (8)	0.72345 (9)	0.0232 (3)
O3	0.76131 (18)	1.06166 (8)	0.50143 (9)	0.0230 (3)
S1	0.40906 (6)	0.68071 (3)	0.61623 (3)	0.02073 (13)
S2	0.33062 (7)	0.49172 (3)	0.66366 (3)	0.02480 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0200 (9)	0.0227 (9)	0.0162 (9)	0.0001 (8)	−0.0020 (7)	0.0015 (7)
C4	0.0181 (9)	0.0193 (9)	0.0149 (8)	−0.0009 (7)	−0.0017 (7)	0.0004 (7)
C5	0.0150 (8)	0.0214 (9)	0.0154 (8)	−0.0006 (7)	−0.0005 (7)	0.0011 (7)
C6	0.0178 (9)	0.0212 (10)	0.0269 (10)	−0.0004 (8)	0.0033 (8)	0.0012 (9)
C7	0.0127 (8)	0.0192 (9)	0.0190 (9)	0.0007 (7)	−0.0020 (7)	0.0018 (7)
C8	0.0189 (9)	0.0206 (9)	0.0182 (9)	0.0024 (7)	−0.0002 (7)	−0.0017 (8)
C9	0.0188 (9)	0.0226 (10)	0.0176 (9)	0.0014 (7)	0.0017 (7)	0.0032 (8)
C10	0.0131 (8)	0.0175 (9)	0.0218 (9)	0.0009 (7)	−0.0023 (7)	0.0026 (7)
C11	0.0161 (9)	0.0217 (9)	0.0194 (9)	0.0035 (7)	−0.0006 (7)	−0.0015 (8)
C12	0.0146 (8)	0.0228 (10)	0.0157 (9)	0.0027 (7)	−0.0004 (7)	0.0029 (7)
C13	0.0220 (10)	0.0202 (10)	0.0278 (10)	−0.0012 (8)	0.0035 (8)	0.0047 (8)
C14	0.0152 (8)	0.0204 (9)	0.0168 (8)	−0.0006 (7)	0.0019 (7)	0.0011 (8)
C15	0.0204 (9)	0.0185 (9)	0.0150 (8)	−0.0002 (7)	0.0007 (7)	0.0006 (7)
C16	0.0204 (9)	0.0244 (10)	0.0175 (9)	−0.0012 (8)	−0.0001 (7)	0.0001 (8)
C17	0.0192 (9)	0.0267 (10)	0.0204 (9)	0.0054 (8)	0.0001 (8)	0.0043 (8)
C18	0.0275 (10)	0.0172 (10)	0.0259 (10)	0.0056 (8)	0.0066 (8)	0.0014 (8)
C19	0.0274 (10)	0.0205 (10)	0.0256 (10)	−0.0020 (8)	−0.0004 (8)	−0.0067 (8)
C20	0.0210 (9)	0.0232 (10)	0.0187 (9)	0.0032 (8)	−0.0028 (8)	−0.0029 (8)
N3	0.0180 (7)	0.0152 (7)	0.0195 (7)	0.0014 (6)	−0.0011 (6)	0.0025 (6)
O1	0.0235 (7)	0.0151 (6)	0.0175 (6)	0.0032 (5)	−0.0018 (5)	0.0001 (5)
O2	0.0276 (7)	0.0196 (7)	0.0218 (7)	−0.0016 (6)	−0.0032 (6)	−0.0018 (6)
O3	0.0273 (7)	0.0182 (7)	0.0235 (7)	−0.0021 (5)	0.0028 (6)	0.0007 (5)
S1	0.0170 (2)	0.0207 (2)	0.0248 (3)	0.00183 (18)	0.00374 (18)	0.00421 (19)
S2	0.0237 (3)	0.0248 (3)	0.0262 (3)	−0.0042 (2)	0.00374 (19)	0.0058 (2)

Geometric parameters (Å, º)

C2—N3	1.357 (2)	C12—H12	0.95 (2)
C2—S2	1.6619 (19)	C13—O3	1.428 (2)
C2—S1	1.7290 (19)	C13—H13A	0.97 (2)
C4—C5	1.352 (3)	C13—H13B	0.96 (2)
C4—N3	1.396 (2)	C13—H13C	0.98 (2)
C4—C6	1.488 (3)	C14—O2	1.192 (2)
C5—C7	1.471 (3)	C14—O1	1.415 (2)
C5—S1	1.7567 (18)	C14—C15	1.476 (3)
C6—H6A	0.93 (2)	C15—C20	1.397 (3)
C6—H6B	0.97 (2)	C15—C16	1.399 (3)
C6—H6C	0.99 (2)	C16—C17	1.386 (3)
C7—C8	1.396 (3)	C16—H16	0.96 (2)
C7—C12	1.398 (3)	C17—C18	1.394 (3)
C8—C9	1.391 (3)	C17—H17	0.94 (2)
C8—H8	0.98 (2)	C18—C19	1.390 (3)
C9—C10	1.386 (3)	C18—H18	0.93 (2)
C9—H9	0.93 (2)	C19—C20	1.382 (3)
C10—O3	1.364 (2)	C19—H19	0.95 (2)
C10—C11	1.398 (3)	C20—H20	0.96 (2)
C11—C12	1.381 (3)	N3—O1	1.3892 (18)
C11—H11	1.11 (2)
N3—C2—S2	126.80 (15)	O3—C13—H13A	110.5 (13)
N3—C2—S1	106.09 (13)	O3—C13—H13B	104.7 (13)
S2—C2—S1	127.11 (11)	H13A—C13—H13B	112.3 (18)
C5—C4—N3	109.99 (16)	O3—C13—H13C	112.4 (13)
C5—C4—C6	130.07 (17)	H13A—C13—H13C	109.4 (18)
N3—C4—C6	119.87 (16)	H13B—C13—H13C	107.5 (18)
C4—C5—C7	130.05 (17)	O2—C14—O1	121.73 (16)
C4—C5—S1	110.83 (14)	O2—C14—C15	128.79 (17)
C7—C5—S1	119.11 (13)	O1—C14—C15	109.48 (14)
C4—C6—H6A	111.8 (13)	C20—C15—C16	120.45 (17)
C4—C6—H6B	109.3 (13)	C20—C15—C14	121.23 (16)
H6A—C6—H6B	107.9 (19)	C16—C15—C14	118.27 (16)
C4—C6—H6C	108.6 (12)	C17—C16—C15	119.61 (18)
H6A—C6—H6C	109.2 (18)	C17—C16—H16	120.7 (13)
H6B—C6—H6C	110.0 (18)	C15—C16—H16	119.7 (13)
C8—C7—C12	118.24 (17)	C16—C17—C18	119.81 (18)
C8—C7—C5	121.66 (16)	C16—C17—H17	118.5 (14)
C12—C7—C5	120.09 (16)	C18—C17—H17	121.7 (14)
C9—C8—C7	121.21 (17)	C19—C18—C17	120.36 (18)
C9—C8—H8	119.6 (12)	C19—C18—H18	119.9 (14)
C7—C8—H8	119.2 (12)	C17—C18—H18	119.7 (13)
C10—C9—C8	119.52 (17)	C20—C19—C18	120.31 (18)
C10—C9—H9	120.4 (13)	C20—C19—H19	118.2 (14)
C8—C9—H9	120.1 (13)	C18—C19—H19	121.5 (14)
O3—C10—C9	125.19 (16)	C19—C20—C15	119.46 (18)
O3—C10—C11	114.63 (16)	C19—C20—H20	121.8 (13)
C9—C10—C11	120.17 (17)	C15—C20—H20	118.8 (13)
C12—C11—C10	119.68 (17)	C2—N3—O1	118.70 (14)
C12—C11—H11	119.3 (11)	C2—N3—C4	119.78 (15)
C10—C11—H11	121.0 (11)	O1—N3—C4	121.42 (14)
C11—C12—C7	121.17 (17)	N3—O1—C14	111.00 (13)
C11—C12—H12	118.7 (13)	C10—O3—C13	117.72 (15)
C7—C12—H12	120.2 (13)	C2—S1—C5	93.27 (9)
N3—C4—C5—C7	−179.85 (17)	C15—C16—C17—C18	−0.6 (3)
C6—C4—C5—C7	3.1 (3)	C16—C17—C18—C19	0.0 (3)
N3—C4—C5—S1	1.10 (18)	C17—C18—C19—C20	0.8 (3)
C6—C4—C5—S1	−175.93 (17)	C18—C19—C20—C15	−1.0 (3)
C4—C5—C7—C8	51.3 (3)	C16—C15—C20—C19	0.5 (3)
S1—C5—C7—C8	−129.72 (16)	C14—C15—C20—C19	−176.98 (17)
C4—C5—C7—C12	−130.1 (2)	S2—C2—N3—O1	−0.8 (2)
S1—C5—C7—C12	48.9 (2)	S1—C2—N3—O1	178.31 (11)
C12—C7—C8—C9	0.4 (3)	S2—C2—N3—C4	−177.12 (13)
C5—C7—C8—C9	178.97 (16)	S1—C2—N3—C4	2.0 (2)
C7—C8—C9—C10	0.0 (3)	C5—C4—N3—C2	−2.1 (2)
C8—C9—C10—O3	178.54 (17)	C6—C4—N3—C2	175.26 (16)
C8—C9—C10—C11	−0.3 (3)	C5—C4—N3—O1	−178.33 (14)
O3—C10—C11—C12	−178.76 (16)	C6—C4—N3—O1	−0.9 (2)
C9—C10—C11—C12	0.2 (3)	C2—N3—O1—C14	−83.74 (18)
C10—C11—C12—C7	0.2 (3)	C4—N3—O1—C14	92.51 (18)
C8—C7—C12—C11	−0.5 (3)	O2—C14—O1—N3	−16.8 (2)
C5—C7—C12—C11	−179.10 (16)	C15—C14—O1—N3	163.86 (14)
O2—C14—C15—C20	149.50 (19)	C9—C10—O3—C13	0.3 (3)
O1—C14—C15—C20	−31.2 (2)	C11—C10—O3—C13	179.19 (16)
O2—C14—C15—C16	−28.0 (3)	N3—C2—S1—C5	−1.02 (13)
O1—C14—C15—C16	151.29 (16)	S2—C2—S1—C5	178.09 (13)
C20—C15—C16—C17	0.3 (3)	C4—C5—S1—C2	−0.05 (14)
C14—C15—C16—C17	177.83 (17)	C7—C5—S1—C2	−179.22 (14)