(Z)-2-Methyl­sulfanyl-1,4-di-p-tolyl­but-2-ene-1,4-dione

The title compound, C₁₉H₁₈O₂S, displays a trans configuration with respect to the central C=C double bond. The dihedral angle between the two aromatic rings is 67.91 (5)°.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.068
• wR factor = 0.152
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               3199
           Count of symmetry unique reflns         1912
           Completeness (_total/calc)            167.31%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1287
           Fraction of Friedel pairs measured     0.673
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

(Z)-2-Methylsulfanyl-1,4-di-p-tolylbut-2-ene-1,4-dione

Crystal data

C19H18O2S	F(000) = 656
Mr = 310.39	Dx = 1.261 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2421 reflections
a = 5.7812 (6) Å	θ = 2.8–18.9°
b = 7.5573 (8) Å	µ = 0.20 mm^−1
c = 37.412 (4) Å	T = 297 K
V = 1634.5 (3) Å^3	Block, yellow
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer	2450 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 26.0°, θmin = 2.2°
φ and ω scans	h = −7→7
12645 measured reflections	k = −9→9
3199 independent reflections	l = −46→45

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.0684P)^2 + 0.2905P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.017
3199 reflections	Δρmax = 0.28 e Å^−3
202 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1287 Friedel pairs???
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (16)

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
C1	−0.2773 (6)	0.4917 (5)	0.80380 (9)	0.0426 (8)
C2	−0.4314 (6)	0.4461 (5)	0.77690 (10)	0.0491 (9)
H2	−0.5730	0.3957	0.7829	0.059*
C3	−0.3789 (6)	0.4737 (5)	0.74204 (10)	0.0509 (9)
H3	−0.4863	0.4436	0.7246	0.061*
C4	−0.1659 (6)	0.5470 (5)	0.73172 (9)	0.0467 (9)
C5	−0.0145 (7)	0.5941 (5)	0.75853 (10)	0.0500 (9)
H5	0.1266	0.6453	0.7526	0.060*
C6	−0.0684 (6)	0.5668 (5)	0.79423 (10)	0.0499 (9)
H6	0.0368	0.5993	0.8118	0.060*
C7	−0.1061 (8)	0.5699 (6)	0.69323 (10)	0.0653 (11)
H7A	−0.0671	0.4571	0.6831	0.098*
H7B	0.0236	0.6485	0.6911	0.098*
H7C	−0.2362	0.6188	0.6807	0.098*
C8	−0.3384 (7)	0.4537 (6)	0.84148 (10)	0.0574 (10)
C9	−0.1783 (7)	0.5166 (5)	0.87087 (9)	0.0498 (9)
C10	−0.0339 (6)	0.3978 (5)	0.88509 (10)	0.0494 (9)
H10	−0.0437	0.2815	0.8771	0.059*
C11	0.1389 (7)	0.4398 (5)	0.91241 (9)	0.0504 (9)
C12	0.2768 (6)	0.2975 (5)	0.92949 (9)	0.0437 (8)
C13	0.4781 (7)	0.3422 (5)	0.94731 (10)	0.0516 (10)
H13	0.5246	0.4599	0.9483	0.062*
C14	0.6109 (6)	0.2131 (5)	0.96374 (10)	0.0536 (9)
H14	0.7477	0.2451	0.9751	0.064*
C15	0.5435 (7)	0.0374 (5)	0.96347 (10)	0.0513 (9)
C16	0.3431 (8)	−0.0055 (5)	0.94603 (11)	0.0609 (11)
H16	0.2959	−0.1231	0.9455	0.073*
C17	0.2090 (7)	0.1205 (5)	0.92919 (10)	0.0552 (10)
H17	0.0733	0.0873	0.9176	0.066*
C18	0.6861 (9)	−0.1008 (6)	0.98144 (12)	0.0755 (13)
H18A	0.6371	−0.1132	1.0058	0.113*
H18B	0.8460	−0.0667	0.9808	0.113*
H18C	0.6671	−0.2116	0.9692	0.113*
C19	−0.4432 (9)	0.8172 (7)	0.86119 (13)	0.0827 (15)
H19A	−0.4230	0.8076	0.8358	0.124*
H19B	−0.4693	0.9387	0.8675	0.124*
H19C	−0.5738	0.7473	0.8684	0.124*
O1	−0.5102 (6)	0.3713 (6)	0.84932 (8)	0.1068 (14)
O2	0.1689 (6)	0.5957 (4)	0.92056 (8)	0.0779 (10)
S1	−0.1891 (2)	0.73875 (15)	0.88330 (3)	0.0687 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0374 (18)	0.047 (2)	0.0429 (19)	−0.0013 (16)	−0.0025 (15)	0.0013 (15)
C2	0.0372 (19)	0.058 (2)	0.053 (2)	0.0019 (18)	−0.0058 (16)	−0.0007 (18)
C3	0.047 (2)	0.065 (2)	0.041 (2)	0.0003 (19)	−0.0119 (16)	−0.0052 (18)
C4	0.049 (2)	0.043 (2)	0.048 (2)	0.0053 (18)	0.0035 (17)	−0.0018 (16)
C5	0.044 (2)	0.050 (2)	0.056 (2)	−0.0071 (18)	0.0031 (19)	−0.0005 (18)
C6	0.043 (2)	0.061 (2)	0.046 (2)	−0.0101 (18)	−0.0057 (16)	−0.0025 (17)
C7	0.072 (3)	0.069 (3)	0.055 (2)	−0.002 (2)	0.007 (2)	0.000 (2)
C8	0.045 (2)	0.079 (3)	0.047 (2)	−0.010 (2)	−0.0016 (18)	−0.001 (2)
C9	0.056 (2)	0.057 (2)	0.0361 (18)	−0.013 (2)	0.0038 (17)	−0.0014 (16)
C10	0.050 (2)	0.055 (2)	0.0437 (19)	−0.0066 (18)	−0.0032 (17)	−0.0094 (18)
C11	0.058 (2)	0.050 (2)	0.0423 (19)	−0.0065 (19)	−0.0022 (17)	−0.0060 (17)
C12	0.050 (2)	0.047 (2)	0.0341 (17)	−0.0021 (17)	0.0020 (16)	−0.0029 (15)
C13	0.055 (2)	0.046 (2)	0.054 (2)	−0.0117 (18)	−0.0040 (19)	−0.0026 (17)
C14	0.045 (2)	0.059 (2)	0.056 (2)	−0.0132 (19)	−0.0107 (18)	−0.001 (2)
C15	0.059 (2)	0.048 (2)	0.046 (2)	0.0008 (19)	0.0048 (19)	−0.0010 (17)
C16	0.074 (3)	0.041 (2)	0.068 (3)	−0.009 (2)	−0.007 (2)	−0.0050 (19)
C17	0.055 (2)	0.053 (2)	0.058 (2)	−0.015 (2)	−0.007 (2)	−0.0060 (19)
C18	0.086 (3)	0.069 (3)	0.071 (3)	0.011 (3)	0.000 (3)	0.008 (2)
C19	0.091 (4)	0.084 (4)	0.073 (3)	0.023 (3)	−0.007 (3)	0.008 (2)
O1	0.076 (2)	0.186 (4)	0.0580 (19)	−0.070 (3)	0.0025 (17)	0.012 (2)
O2	0.104 (3)	0.0475 (17)	0.083 (2)	−0.0070 (17)	−0.0373 (19)	−0.0087 (14)
S1	0.0872 (8)	0.0596 (6)	0.0591 (6)	0.0045 (6)	−0.0110 (6)	0.0010 (6)

Geometric parameters (Å, º)

C1—C6	1.381 (5)	C11—O2	1.229 (5)
C1—C2	1.388 (5)	C11—C12	1.483 (5)
C1—C8	1.481 (5)	C12—C13	1.383 (5)
C2—C3	1.355 (5)	C12—C17	1.394 (5)
C2—H2	0.9300	C13—C14	1.385 (5)
C3—C4	1.404 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.384 (5)
C4—C5	1.378 (5)	C14—H14	0.9300
C4—C7	1.491 (5)	C15—C16	1.368 (6)
C5—C6	1.387 (5)	C15—C18	1.491 (6)
C5—H5	0.9300	C16—C17	1.380 (5)
C6—H6	0.9300	C16—H16	0.9300
C7—H7A	0.9600	C17—H17	0.9300
C7—H7B	0.9600	C18—H18A	0.9600
C7—H7C	0.9600	C18—H18B	0.9600
C8—O1	1.209 (5)	C18—H18C	0.9600
C8—C9	1.514 (5)	C19—S1	1.787 (5)
C9—C10	1.336 (5)	C19—H19A	0.9600
C9—S1	1.743 (4)	C19—H19B	0.9600
C10—C11	1.464 (5)	C19—H19C	0.9600
C10—H10	0.9300
C6—C1—C2	118.4 (3)	O2—C11—C12	120.8 (3)
C6—C1—C8	122.3 (3)	C10—C11—C12	120.7 (3)
C2—C1—C8	119.3 (3)	C13—C12—C17	118.3 (3)
C3—C2—C1	121.0 (3)	C13—C12—C11	118.9 (3)
C3—C2—H2	119.5	C17—C12—C11	122.7 (4)
C1—C2—H2	119.5	C12—C13—C14	120.6 (3)
C2—C3—C4	121.5 (3)	C12—C13—H13	119.7
C2—C3—H3	119.3	C14—C13—H13	119.7
C4—C3—H3	119.3	C15—C14—C13	121.1 (3)
C5—C4—C3	117.3 (3)	C15—C14—H14	119.5
C5—C4—C7	121.7 (4)	C13—C14—H14	119.5
C3—C4—C7	121.0 (3)	C16—C15—C14	118.0 (4)
C4—C5—C6	121.3 (3)	C16—C15—C18	121.1 (4)
C4—C5—H5	119.3	C14—C15—C18	120.9 (4)
C6—C5—H5	119.3	C15—C16—C17	122.0 (4)
C1—C6—C5	120.5 (3)	C15—C16—H16	119.0
C1—C6—H6	119.8	C17—C16—H16	119.0
C5—C6—H6	119.8	C16—C17—C12	120.0 (4)
C4—C7—H7A	109.5	C16—C17—H17	120.0
C4—C7—H7B	109.5	C12—C17—H17	120.0
H7A—C7—H7B	109.5	C15—C18—H18A	109.5
C4—C7—H7C	109.5	C15—C18—H18B	109.5
H7A—C7—H7C	109.5	H18A—C18—H18B	109.5
H7B—C7—H7C	109.5	C15—C18—H18C	109.5
O1—C8—C1	121.8 (3)	H18A—C18—H18C	109.5
O1—C8—C9	119.2 (3)	H18B—C18—H18C	109.5
C1—C8—C9	119.0 (3)	S1—C19—H19A	109.5
C10—C9—C8	117.4 (3)	S1—C19—H19B	109.5
C10—C9—S1	124.3 (3)	H19A—C19—H19B	109.5
C8—C9—S1	118.3 (3)	S1—C19—H19C	109.5
C9—C10—C11	124.0 (3)	H19A—C19—H19C	109.5
C9—C10—H10	118.0	H19B—C19—H19C	109.5
C11—C10—H10	118.0	C9—S1—C19	103.0 (2)
O2—C11—C10	118.5 (4)
C6—C1—C2—C3	0.2 (6)	S1—C9—C10—C11	−1.7 (5)
C8—C1—C2—C3	−178.0 (4)	C9—C10—C11—O2	−7.0 (6)
C1—C2—C3—C4	1.0 (6)	C9—C10—C11—C12	173.9 (3)
C2—C3—C4—C5	−1.7 (5)	O2—C11—C12—C13	−16.9 (5)
C2—C3—C4—C7	177.4 (4)	C10—C11—C12—C13	162.2 (3)
C3—C4—C5—C6	1.3 (5)	O2—C11—C12—C17	161.3 (4)
C7—C4—C5—C6	−177.8 (4)	C10—C11—C12—C17	−19.6 (5)
C2—C1—C6—C5	−0.5 (6)	C17—C12—C13—C14	1.4 (5)
C8—C1—C6—C5	177.6 (4)	C11—C12—C13—C14	179.7 (3)
C4—C5—C6—C1	−0.3 (6)	C12—C13—C14—C15	−1.5 (6)
C6—C1—C8—O1	−172.0 (4)	C13—C14—C15—C16	0.9 (6)
C2—C1—C8—O1	6.1 (6)	C13—C14—C15—C18	−179.5 (4)
C6—C1—C8—C9	6.6 (5)	C14—C15—C16—C17	−0.3 (6)
C2—C1—C8—C9	−175.3 (3)	C18—C15—C16—C17	−179.9 (4)
O1—C8—C9—C10	78.5 (5)	C15—C16—C17—C12	0.3 (6)
C1—C8—C9—C10	−100.2 (4)	C13—C12—C17—C16	−0.8 (5)
O1—C8—C9—S1	−102.8 (5)	C11—C12—C17—C16	−179.0 (3)
C1—C8—C9—S1	78.5 (4)	C10—C9—S1—C19	−170.3 (3)
C8—C9—C10—C11	176.9 (3)	C8—C9—S1—C19	11.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2^i	0.93	2.43	3.318 (5)	159

Symmetry code: (i) x, y−1, z.