Weak inter­molecular inter­actions in a series of biologically active 4′-methyl­thio-trans-stilbenes

The crystal structures of nine meth­oxy-substituted 4′-methyl­thiostilbenes, which are potential inhibitors of human recombinant cytochrome P450 enzymes, were determined. These com­pounds included two mono-meth­oxy-substituted derivatives: 2-meth­oxy-4′-methyl­thio-trans-stilbene {systematic name: 1-[(E)-2-(2-methoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene} (1) and 3-meth­oxy-4′-methyl­thio-trans-stilbene (2), both C₁₆H₁₆OS; four dimeth­oxy derivatives: 2,3-dimeth­oxy-4′-methyl­thio-trans-stilbene (3), 2,5-dimeth­oxy-4′-methyl­thio-trans-stilbene (4), 3,5-dimeth­oxy-4′-methyl­thio-trans-stilbene (5) and 2,4-dimeth­oxy-4′-methyl­thio-trans-stilbene (6), all C₁₇H₁₈O₂S; and three trimeth­oxy com­pounds: 2,4,5-trimeth­oxy-4′-methyl­thio-trans-stilbene (7), 3,4,5-trimeth­oxy-4′-methyl­thio-trans-stilbene (8) and 2,4,6-trimeth­oxy-4′-methyl­thio-trans-stilbene (9), all C₁₈H₂₀O₃S. The geometries of the com­pounds in the crystal structures were com­pared with those found during docking studies at the active site of the receptor, and some relevant differences were identified. Inter­molecular inter­actions were analyzed using three different methods. First, the (3,−1) critical points of the gradient field of the electron density were identified, and then the appropriate contacts were analyzed using their geometrical characteristics and inter­action energy calculations. The results confirmed the importance of weak delocalized inter­actions in the construction of the crystal structures, and the results of different methods (PIXEL and DFT) were com­parable in the absence of strong well-defined inter­molecular inter­actions.

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021). Data reduction: CrysAlis PRO (Rigaku OD, 2021) for (1), (2), (3), (5), (6), (7), (8), (9); CrysAlis PRO (Rigaku OD, 2021)) for (4). For all structures, program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

1-[(E)-2-(2-Methoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene (1)

Crystal data

C16H16OS	Dx = 1.298 Mg m^−3
Mr = 256.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 800 reflections
a = 5.4591 (3) Å	θ = 4.1–27.5°
b = 9.6001 (4) Å	µ = 0.23 mm^−1
c = 25.0301 (15) Å	T = 100 K
V = 1311.78 (12) Å^3	Prism, colourless
Z = 4	0.25 × 0.1 × 0.05 mm
F(000) = 544

Data collection

Rigaku OD Xcalibur Eos diffractometer	2477 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 16.1544 pixels mm^-1	θmax = 28.1°, θmin = 3.2°
ω scans	h = −6→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −12→7
Tmin = 0.959, Tmax = 1.000	l = −31→31
3576 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0312P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.33 e Å^−3
2477 reflections	Δρmin = −0.29 e Å^−3
165 parameters	Absolute structure: Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.00 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.4690 (7)	0.2435 (4)	0.36952 (15)	0.0150 (8)
C2	0.3137 (7)	0.2446 (4)	0.32457 (16)	0.0159 (9)
O2	0.1420 (5)	0.3480 (3)	0.32389 (11)	0.0215 (7)
C21	−0.0332 (7)	0.3487 (4)	0.28211 (15)	0.0205 (9)
H21A	0.0485	0.3692	0.2482	0.031*
H21B	−0.1571	0.4201	0.2893	0.031*
H21C	−0.1123	0.2572	0.2800	0.031*
C3	0.3394 (7)	0.1468 (4)	0.28426 (16)	0.0202 (10)
H3	0.2350	0.1495	0.2539	0.024*
C4	0.5191 (7)	0.0446 (4)	0.28851 (15)	0.0177 (9)
H4	0.5348	−0.0239	0.2613	0.021*
C5	0.6744 (7)	0.0420 (4)	0.33183 (16)	0.0180 (9)
H5	0.7988	−0.0269	0.3342	0.022*
C6	0.6481 (6)	0.1407 (4)	0.37199 (17)	0.0161 (9)
H6	0.7551	0.1378	0.4019	0.019*
C7	0.4325 (7)	0.3478 (4)	0.41156 (15)	0.0159 (9)
H7	0.2896	0.4039	0.4091	0.019*
C8	0.5791 (7)	0.3713 (4)	0.45258 (17)	0.0170 (9)
H8	0.7214	0.3147	0.4548	0.020*
C1'	0.5468 (8)	0.4751 (4)	0.49505 (16)	0.0165 (9)
C2'	0.7208 (7)	0.4872 (4)	0.53472 (17)	0.0171 (10)
H2'	0.8555	0.4246	0.5347	0.021*
C3'	0.7069 (7)	0.5868 (4)	0.57445 (17)	0.0183 (10)
H3'	0.8318	0.5926	0.6008	0.022*
C4'	0.5100 (7)	0.6784 (4)	0.57577 (14)	0.0147 (8)
S4'	0.47619 (18)	0.81219 (10)	0.62346 (4)	0.0191 (3)
C41'	0.7708 (7)	0.8160 (4)	0.65513 (16)	0.0231 (10)
H41A	0.7964	0.7290	0.6749	0.035*
H41B	0.7784	0.8949	0.6799	0.035*
H41C	0.8986	0.8261	0.6279	0.035*
C5'	0.3291 (7)	0.6657 (4)	0.53679 (15)	0.0160 (9)
H5'	0.1927	0.7271	0.5373	0.019*
C6'	0.3454 (7)	0.5651 (4)	0.49744 (17)	0.0163 (9)
H6'	0.2183	0.5569	0.4717	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.018 (2)	0.0114 (16)	0.016 (2)	−0.0027 (19)	0.001 (2)	0.0016 (17)
C2	0.018 (2)	0.0095 (18)	0.021 (2)	0.0003 (19)	0.0005 (19)	0.0037 (19)
O2	0.0218 (15)	0.0147 (15)	0.0280 (17)	0.0031 (13)	−0.0099 (13)	−0.0032 (14)
C21	0.020 (2)	0.017 (2)	0.025 (2)	0.002 (2)	−0.009 (2)	0.0047 (18)
C3	0.022 (2)	0.023 (2)	0.016 (2)	−0.004 (2)	−0.0053 (19)	0.002 (2)
C4	0.022 (2)	0.0116 (17)	0.020 (2)	−0.006 (2)	0.003 (2)	−0.0042 (17)
C5	0.017 (2)	0.017 (2)	0.019 (2)	0.003 (2)	0.005 (2)	0.0032 (19)
C6	0.0136 (19)	0.018 (2)	0.017 (2)	−0.0005 (18)	−0.0002 (19)	0.002 (2)
C7	0.013 (2)	0.016 (2)	0.019 (2)	0.0036 (18)	0.0025 (17)	0.0010 (18)
C8	0.016 (2)	0.0118 (19)	0.023 (2)	0.0010 (17)	−0.0005 (18)	0.0025 (19)
C1'	0.018 (2)	0.0139 (19)	0.018 (2)	−0.0009 (19)	0.0006 (19)	0.0015 (17)
C2'	0.015 (2)	0.011 (2)	0.025 (2)	0.0020 (18)	0.0010 (19)	0.0024 (19)
C3'	0.012 (2)	0.019 (2)	0.024 (2)	0.0013 (19)	−0.0043 (19)	0.002 (2)
C4'	0.0173 (19)	0.0110 (17)	0.0158 (18)	−0.005 (2)	0.0020 (18)	0.0001 (17)
S4'	0.0188 (5)	0.0159 (5)	0.0226 (5)	0.0007 (5)	0.0013 (5)	−0.0035 (5)
C41'	0.025 (2)	0.019 (2)	0.025 (2)	0.001 (2)	−0.0047 (19)	−0.005 (2)
C5'	0.0139 (19)	0.014 (2)	0.020 (2)	0.001 (2)	0.0036 (18)	0.0034 (19)
C6'	0.015 (2)	0.016 (2)	0.018 (2)	−0.001 (2)	−0.0011 (19)	0.001 (2)

Geometric parameters (Å, º)

C1—C6	1.391 (5)	C8—C1'	1.467 (5)
C1—C2	1.409 (5)	C8—H8	0.9500
C1—C7	1.466 (5)	C1'—C2'	1.379 (5)
C2—O2	1.365 (4)	C1'—C6'	1.400 (5)
C2—C3	1.385 (5)	C2'—C3'	1.381 (5)
O2—C21	1.417 (4)	C2'—H2'	0.9500
C21—H21A	0.9800	C3'—C4'	1.389 (5)
C21—H21B	0.9800	C3'—H3'	0.9500
C21—H21C	0.9800	C4'—C5'	1.393 (5)
C3—C4	1.392 (5)	C4'—S4'	1.763 (4)
C3—H3	0.9500	S4'—C41'	1.794 (4)
C4—C5	1.376 (5)	C41'—H41A	0.9800
C4—H4	0.9500	C41'—H41B	0.9800
C5—C6	1.388 (5)	C41'—H41C	0.9800
C5—H5	0.9500	C5'—C6'	1.382 (5)
C6—H6	0.9500	C5'—H5'	0.9500
C7—C8	1.321 (5)	C6'—H6'	0.9500
C7—H7	0.9500
C6—C1—C2	117.6 (4)	C7—C8—C1'	127.3 (4)
C6—C1—C7	123.3 (4)	C7—C8—H8	116.3
C2—C1—C7	119.1 (4)	C1'—C8—H8	116.3
O2—C2—C3	123.6 (4)	C2'—C1'—C6'	117.3 (4)
O2—C2—C1	115.4 (3)	C2'—C1'—C8	119.8 (4)
C3—C2—C1	121.1 (4)	C6'—C1'—C8	123.0 (4)
C2—O2—C21	118.4 (3)	C1'—C2'—C3'	122.6 (4)
O2—C21—H21A	109.5	C1'—C2'—H2'	118.7
O2—C21—H21B	109.5	C3'—C2'—H2'	118.7
H21A—C21—H21B	109.5	C2'—C3'—C4'	119.8 (4)
O2—C21—H21C	109.5	C2'—C3'—H3'	120.1
H21A—C21—H21C	109.5	C4'—C3'—H3'	120.1
H21B—C21—H21C	109.5	C3'—C4'—C5'	118.5 (3)
C2—C3—C4	119.6 (4)	C3'—C4'—S4'	123.9 (3)
C2—C3—H3	120.2	C5'—C4'—S4'	117.6 (3)
C4—C3—H3	120.2	C4'—S4'—C41'	102.71 (19)
C5—C4—C3	120.5 (4)	S4'—C41'—H41A	109.5
C5—C4—H4	119.8	S4'—C41'—H41B	109.5
C3—C4—H4	119.8	H41A—C41'—H41B	109.5
C4—C5—C6	119.6 (4)	S4'—C41'—H41C	109.5
C4—C5—H5	120.2	H41A—C41'—H41C	109.5
C6—C5—H5	120.2	H41B—C41'—H41C	109.5
C5—C6—C1	121.6 (4)	C6'—C5'—C4'	120.9 (4)
C5—C6—H6	119.2	C6'—C5'—H5'	119.5
C1—C6—H6	119.2	C4'—C5'—H5'	119.5
C8—C7—C1	126.3 (4)	C5'—C6'—C1'	120.8 (4)
C8—C7—H7	116.8	C5'—C6'—H6'	119.6
C1—C7—H7	116.8	C1'—C6'—H6'	119.6
C6—C1—C2—O2	−179.6 (3)	C1—C7—C8—C1'	179.9 (3)
C7—C1—C2—O2	1.5 (5)	C7—C8—C1'—C2'	−179.0 (4)
C6—C1—C2—C3	−0.2 (5)	C7—C8—C1'—C6'	0.6 (6)
C7—C1—C2—C3	−179.1 (3)	C6'—C1'—C2'—C3'	−2.6 (6)
C3—C2—O2—C21	5.6 (5)	C8—C1'—C2'—C3'	177.0 (4)
C1—C2—O2—C21	−174.9 (3)	C1'—C2'—C3'—C4'	0.9 (6)
O2—C2—C3—C4	−179.7 (3)	C2'—C3'—C4'—C5'	0.7 (6)
C1—C2—C3—C4	0.9 (6)	C2'—C3'—C4'—S4'	−178.4 (3)
C2—C3—C4—C5	−1.4 (6)	C3'—C4'—S4'—C41'	11.4 (4)
C3—C4—C5—C6	1.2 (6)	C5'—C4'—S4'—C41'	−167.7 (3)
C4—C5—C6—C1	−0.5 (6)	C3'—C4'—C5'—C6'	−0.4 (6)
C2—C1—C6—C5	0.0 (5)	S4'—C4'—C5'—C6'	178.7 (3)
C7—C1—C6—C5	178.8 (4)	C4'—C5'—C6'—C1'	−1.4 (6)
C6—C1—C7—C8	10.0 (6)	C2'—C1'—C6'—C5'	2.8 (6)
C2—C1—C7—C8	−171.2 (4)	C8—C1'—C6'—C5'	−176.8 (4)

1-[(E)-2-(3-Methoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene (2)

Crystal data

C16H16OS	Dx = 1.282 Mg m^−3
Mr = 256.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 971 reflections
a = 5.1311 (3) Å	θ = 3.6–27.8°
b = 9.1135 (6) Å	µ = 0.23 mm^−1
c = 28.400 (3) Å	T = 100 K
V = 1328.05 (18) Å^3	Plate, colourless
Z = 4	0.3 × 0.3 × 0.07 mm
F(000) = 544

Data collection

Rigaku OD Xcalibur Eos diffractometer	2562 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2259 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.1544 pixels mm^-1	θmax = 28.2°, θmin = 2.9°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −11→10
Tmin = 0.951, Tmax = 1.000	l = −34→21
3419 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.057	w = 1/[σ^2(Fo^2) + (0.0143P)^2 + 0.5123P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.36 e Å^−3
2562 reflections	Δρmin = −0.27 e Å^−3
165 parameters	Absolute structure: Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.02 (8)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.6014 (8)	0.6600 (4)	0.61620 (14)	0.0213 (9)
C2	0.5497 (8)	0.5590 (4)	0.58017 (14)	0.0186 (9)
H2	0.4121	0.4902	0.5839	0.022*
C3	0.6969 (8)	0.5582 (4)	0.53917 (14)	0.0203 (9)
O3	0.6602 (6)	0.4624 (3)	0.50237 (10)	0.0257 (7)
C31	0.4398 (8)	0.3678 (4)	0.50552 (16)	0.0300 (11)
H31A	0.4270	0.3088	0.4768	0.045*
H31B	0.2814	0.4268	0.5092	0.045*
H31C	0.4595	0.3029	0.5328	0.045*
C4	0.8969 (8)	0.6592 (4)	0.53316 (14)	0.0225 (10)
H4	0.9977	0.6591	0.5051	0.027*
C5	0.9482 (8)	0.7601 (4)	0.56845 (15)	0.0253 (10)
H5	1.0853	0.8291	0.5645	0.030*
C6	0.8006 (7)	0.7615 (5)	0.60971 (14)	0.0247 (10)
H6	0.8364	0.8321	0.6335	0.030*
C7	0.4379 (8)	0.6518 (4)	0.65869 (14)	0.0209 (10)
H7	0.2955	0.5852	0.6579	0.025*
C8	0.4701 (8)	0.7286 (4)	0.69810 (14)	0.0223 (9)
H8	0.6110	0.7962	0.6987	0.027*
C1'	0.3094 (7)	0.7192 (4)	0.74085 (14)	0.0190 (9)
C2'	0.3578 (9)	0.8161 (4)	0.77820 (14)	0.0231 (10)
H2'	0.4930	0.8866	0.7752	0.028*
C3'	0.2140 (8)	0.8116 (4)	0.81928 (14)	0.0230 (10)
H3'	0.2501	0.8798	0.8437	0.028*
C4'	0.0167 (7)	0.7082 (4)	0.82530 (13)	0.0173 (8)
S4'	−0.1444 (2)	0.70989 (11)	0.87990 (4)	0.0268 (3)
C41'	−0.3694 (8)	0.5594 (4)	0.87630 (15)	0.0269 (10)
H41A	−0.4900	0.5757	0.8501	0.040*
H41B	−0.4680	0.5523	0.9058	0.040*
H41C	−0.2730	0.4680	0.8711	0.040*
C5'	−0.0359 (8)	0.6109 (4)	0.78850 (14)	0.0205 (9)
H5'	−0.1706	0.5402	0.7918	0.025*
C6'	0.1081 (8)	0.6172 (4)	0.74710 (14)	0.0242 (10)
H6'	0.0689	0.5505	0.7224	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.018 (2)	0.0231 (19)	0.022 (2)	0.0102 (18)	−0.0016 (19)	0.0044 (18)
C2	0.018 (2)	0.0145 (19)	0.023 (2)	0.0055 (19)	0.0020 (18)	0.0046 (17)
C3	0.020 (2)	0.019 (2)	0.022 (2)	0.0061 (19)	−0.0009 (18)	0.0057 (17)
O3	0.0292 (16)	0.0221 (14)	0.0259 (16)	−0.0042 (15)	0.0074 (15)	−0.0023 (13)
C31	0.030 (3)	0.029 (2)	0.031 (3)	−0.003 (2)	0.007 (2)	−0.004 (2)
C4	0.017 (2)	0.029 (2)	0.022 (2)	0.0035 (19)	0.0033 (18)	0.0064 (18)
C5	0.014 (2)	0.026 (2)	0.036 (3)	−0.0019 (19)	−0.0014 (19)	0.004 (2)
C6	0.018 (2)	0.029 (2)	0.027 (2)	0.0022 (19)	−0.0038 (18)	−0.0025 (19)
C7	0.021 (2)	0.017 (2)	0.026 (2)	0.0036 (18)	−0.0017 (19)	−0.0004 (18)
C8	0.016 (2)	0.021 (2)	0.030 (2)	−0.0035 (19)	−0.0034 (18)	0.0036 (19)
C1'	0.017 (2)	0.0180 (19)	0.022 (2)	0.0066 (19)	−0.0053 (17)	0.0053 (17)
C2'	0.024 (2)	0.0130 (19)	0.032 (2)	0.001 (2)	−0.005 (2)	0.0031 (18)
C3'	0.027 (2)	0.020 (2)	0.022 (2)	0.0016 (19)	−0.0078 (19)	0.0001 (18)
C4'	0.0145 (19)	0.0166 (19)	0.021 (2)	0.0090 (19)	−0.0044 (16)	−0.0012 (18)
S4'	0.0308 (6)	0.0277 (5)	0.0220 (5)	−0.0001 (6)	0.0017 (5)	−0.0056 (5)
C41'	0.029 (2)	0.022 (2)	0.029 (2)	0.001 (2)	0.006 (2)	0.002 (2)
C5'	0.012 (2)	0.023 (2)	0.026 (2)	−0.0024 (19)	0.0001 (18)	−0.0013 (19)
C6'	0.023 (2)	0.024 (2)	0.025 (2)	0.003 (2)	−0.006 (2)	−0.0093 (19)

Geometric parameters (Å, º)

C1—C6	1.391 (5)	C8—C1'	1.470 (5)
C1—C2	1.401 (5)	C8—H8	0.9500
C1—C7	1.472 (5)	C1'—C6'	1.401 (5)
C2—C3	1.388 (5)	C1'—C2'	1.402 (5)
C2—H2	0.9500	C2'—C3'	1.381 (5)
C3—O3	1.375 (4)	C2'—H2'	0.9500
C3—C4	1.389 (5)	C3'—C4'	1.393 (5)
O3—C31	1.424 (4)	C3'—H3'	0.9500
C31—H31A	0.9800	C4'—C5'	1.397 (5)
C31—H31B	0.9800	C4'—S4'	1.757 (4)
C31—H31C	0.9800	S4'—C41'	1.796 (4)
C4—C5	1.386 (5)	C41'—H41A	0.9800
C4—H4	0.9500	C41'—H41B	0.9800
C5—C6	1.395 (5)	C41'—H41C	0.9800
C5—H5	0.9500	C5'—C6'	1.390 (5)
C6—H6	0.9500	C5'—H5'	0.9500
C7—C8	1.330 (5)	C6'—H6'	0.9500
C7—H7	0.9500
C6—C1—C2	118.6 (4)	C7—C8—C1'	126.5 (4)
C6—C1—C7	124.1 (4)	C7—C8—H8	116.8
C2—C1—C7	117.2 (4)	C1'—C8—H8	116.8
C3—C2—C1	120.9 (4)	C6'—C1'—C2'	116.9 (4)
C3—C2—H2	119.6	C6'—C1'—C8	123.8 (4)
C1—C2—H2	119.6	C2'—C1'—C8	119.3 (4)
O3—C3—C2	124.5 (4)	C3'—C2'—C1'	121.7 (4)
O3—C3—C4	115.4 (4)	C3'—C2'—H2'	119.1
C2—C3—C4	120.1 (4)	C1'—C2'—H2'	119.1
C3—O3—C31	116.4 (3)	C2'—C3'—C4'	120.8 (4)
O3—C31—H31A	109.5	C2'—C3'—H3'	119.6
O3—C31—H31B	109.5	C4'—C3'—H3'	119.6
H31A—C31—H31B	109.5	C3'—C4'—C5'	118.5 (4)
O3—C31—H31C	109.5	C3'—C4'—S4'	116.4 (3)
H31A—C31—H31C	109.5	C5'—C4'—S4'	125.1 (3)
H31B—C31—H31C	109.5	C4'—S4'—C41'	104.2 (2)
C5—C4—C3	119.4 (4)	S4'—C41'—H41A	109.5
C5—C4—H4	120.3	S4'—C41'—H41B	109.5
C3—C4—H4	120.3	H41A—C41'—H41B	109.5
C4—C5—C6	120.7 (4)	S4'—C41'—H41C	109.5
C4—C5—H5	119.6	H41A—C41'—H41C	109.5
C6—C5—H5	119.6	H41B—C41'—H41C	109.5
C1—C6—C5	120.3 (4)	C6'—C5'—C4'	120.3 (4)
C1—C6—H6	119.9	C6'—C5'—H5'	119.9
C5—C6—H6	119.9	C4'—C5'—H5'	119.9
C8—C7—C1	126.3 (4)	C5'—C6'—C1'	121.8 (4)
C8—C7—H7	116.8	C5'—C6'—H6'	119.1
C1—C7—H7	116.8	C1'—C6'—H6'	119.1
C6—C1—C2—C3	1.2 (5)	C7—C8—C1'—C6'	5.3 (6)
C7—C1—C2—C3	−179.2 (3)	C7—C8—C1'—C2'	−175.2 (4)
C1—C2—C3—O3	179.5 (3)	C6'—C1'—C2'—C3'	−0.1 (6)
C1—C2—C3—C4	−0.6 (6)	C8—C1'—C2'—C3'	−179.6 (4)
C2—C3—O3—C31	6.1 (5)	C1'—C2'—C3'—C4'	1.0 (6)
C4—C3—O3—C31	−173.8 (3)	C2'—C3'—C4'—C5'	−1.2 (5)
O3—C3—C4—C5	−180.0 (3)	C2'—C3'—C4'—S4'	177.9 (3)
C2—C3—C4—C5	0.2 (6)	C3'—C4'—S4'—C41'	−177.2 (3)
C3—C4—C5—C6	−0.3 (6)	C5'—C4'—S4'—C41'	1.9 (4)
C2—C1—C6—C5	−1.2 (5)	C3'—C4'—C5'—C6'	0.5 (5)
C7—C1—C6—C5	179.2 (4)	S4'—C4'—C5'—C6'	−178.5 (3)
C4—C5—C6—C1	0.8 (6)	C4'—C5'—C6'—C1'	0.4 (6)
C6—C1—C7—C8	−6.7 (6)	C2'—C1'—C6'—C5'	−0.6 (6)
C2—C1—C7—C8	173.8 (4)	C8—C1'—C6'—C5'	178.9 (4)
C1—C7—C8—C1'	−179.1 (4)

1-[(E)-2-(2,3-Dimethoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene (3)

Crystal data

C17H18O2S	F(000) = 608
Mr = 286.37	Dx = 1.328 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 14.0829 (5) Å	Cell parameters from 3025 reflections
b = 7.7490 (2) Å	θ = 3.8–28.0°
c = 14.6419 (5) Å	µ = 0.22 mm^−1
β = 116.329 (5)°	T = 100 K
V = 1432.09 (10) Å^3	Plate, colourless
Z = 4	0.4 × 0.35 × 0.1 mm

Data collection

Rigaku OD Xcalibur Eos diffractometer	2970 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2630 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 16.1544 pixels mm^-1	θmax = 28.1°, θmin = 3.1°
ω scans	h = −12→18
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −10→6
Tmin = 0.986, Tmax = 1.000	l = −19→11
5609 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	All H-atom parameters refined
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.4309P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2970 reflections	Δρmax = 0.30 e Å^−3
253 parameters	Δρmin = −0.24 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.45701 (10)	0.43364 (15)	0.74413 (9)	0.0155 (3)
C2	0.43835 (10)	0.33080 (16)	0.81282 (9)	0.0156 (3)
O2	0.34881 (7)	0.22860 (11)	0.77748 (7)	0.0188 (2)
C21	0.27433 (11)	0.2782 (2)	0.81487 (11)	0.0231 (3)
H21A	0.2467 (12)	0.397 (2)	0.7903 (12)	0.023 (4)*
H21B	0.2149 (14)	0.197 (2)	0.7834 (13)	0.033 (4)*
H21C	0.3047 (13)	0.271 (2)	0.8879 (13)	0.030 (4)*
C3	0.51242 (10)	0.32207 (16)	0.91568 (9)	0.0164 (3)
O3	0.48852 (7)	0.20862 (11)	0.97349 (6)	0.0204 (2)
C31	0.55806 (11)	0.20306 (18)	1.07989 (9)	0.0198 (3)
H31A	0.5635 (12)	0.320 (2)	1.1109 (11)	0.024 (4)*
H31B	0.5272 (12)	0.121 (2)	1.1085 (12)	0.024 (4)*
H31C	0.6313 (13)	0.164 (2)	1.0909 (12)	0.030 (4)*
C4	0.60362 (10)	0.42114 (16)	0.95087 (10)	0.0182 (3)
H4	0.6544 (12)	0.4153 (18)	1.0197 (12)	0.022 (4)*
C5	0.62203 (10)	0.52447 (17)	0.88276 (10)	0.0193 (3)
H5	0.6853 (13)	0.591 (2)	0.9060 (12)	0.025 (4)*
C6	0.55105 (10)	0.52982 (17)	0.78137 (10)	0.0176 (3)
H6	0.5648 (11)	0.6009 (18)	0.7362 (11)	0.015 (3)*
C7	0.37811 (10)	0.44027 (16)	0.63709 (10)	0.0161 (3)
H7	0.3143 (12)	0.3798 (19)	0.6230 (11)	0.020 (4)*
C8	0.38876 (10)	0.52302 (16)	0.56226 (10)	0.0165 (3)
H8	0.4531 (14)	0.579 (2)	0.5745 (12)	0.031 (4)*
C1'	0.30811 (10)	0.53745 (15)	0.45660 (9)	0.0156 (3)
C2'	0.33172 (10)	0.61970 (17)	0.38423 (10)	0.0181 (3)
H2'	0.4004 (12)	0.6679 (19)	0.4051 (11)	0.021 (4)*
C3'	0.25745 (10)	0.63592 (17)	0.28409 (10)	0.0193 (3)
H3'	0.2757 (12)	0.695 (2)	0.2366 (11)	0.023 (4)*
C4'	0.15632 (10)	0.56832 (15)	0.25212 (9)	0.0160 (3)
S4'	0.06726 (3)	0.58863 (4)	0.12217 (2)	0.01970 (11)
C41'	−0.05819 (12)	0.5358 (2)	0.11947 (11)	0.0259 (3)
H41A	−0.1102 (14)	0.558 (2)	0.0515 (14)	0.034 (4)*
H41B	−0.0621 (14)	0.414 (2)	0.1333 (14)	0.040 (5)*
H41C	−0.0704 (13)	0.609 (2)	0.1677 (13)	0.032 (4)*
C5'	0.13086 (11)	0.48759 (18)	0.32301 (10)	0.0209 (3)
H5'	0.0633 (13)	0.441 (2)	0.3048 (12)	0.026 (4)*
C6'	0.20539 (11)	0.47441 (18)	0.42308 (10)	0.0212 (3)
H6'	0.1864 (13)	0.420 (2)	0.4712 (12)	0.029 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0181 (6)	0.0130 (6)	0.0157 (6)	0.0026 (5)	0.0079 (5)	−0.0015 (4)
C2	0.0173 (6)	0.0125 (6)	0.0164 (6)	−0.0003 (5)	0.0069 (5)	−0.0025 (5)
O2	0.0218 (5)	0.0179 (4)	0.0159 (4)	−0.0062 (4)	0.0077 (4)	−0.0025 (3)
C21	0.0206 (7)	0.0301 (8)	0.0182 (7)	−0.0072 (6)	0.0083 (5)	−0.0015 (6)
C3	0.0214 (6)	0.0130 (5)	0.0158 (6)	0.0031 (5)	0.0092 (5)	0.0000 (5)
O3	0.0262 (5)	0.0178 (5)	0.0124 (4)	−0.0034 (4)	0.0043 (4)	0.0023 (3)
C31	0.0233 (7)	0.0216 (7)	0.0122 (6)	0.0028 (6)	0.0059 (5)	0.0014 (5)
C4	0.0188 (6)	0.0180 (6)	0.0144 (6)	0.0037 (5)	0.0043 (5)	−0.0015 (5)
C5	0.0157 (6)	0.0195 (6)	0.0215 (6)	−0.0012 (5)	0.0073 (5)	−0.0028 (5)
C6	0.0188 (6)	0.0174 (6)	0.0184 (6)	0.0016 (5)	0.0100 (5)	0.0003 (5)
C7	0.0166 (6)	0.0150 (6)	0.0169 (6)	0.0000 (5)	0.0075 (5)	−0.0014 (5)
C8	0.0163 (6)	0.0157 (6)	0.0174 (6)	−0.0005 (5)	0.0073 (5)	−0.0013 (5)
C1'	0.0191 (6)	0.0135 (6)	0.0154 (6)	0.0016 (5)	0.0087 (5)	0.0001 (5)
C2'	0.0173 (6)	0.0192 (6)	0.0209 (6)	0.0010 (5)	0.0113 (5)	0.0016 (5)
C3'	0.0228 (7)	0.0211 (6)	0.0195 (6)	0.0037 (5)	0.0144 (5)	0.0041 (5)
C4'	0.0216 (6)	0.0142 (6)	0.0137 (6)	0.0035 (5)	0.0090 (5)	−0.0006 (5)
S4'	0.02295 (18)	0.02334 (18)	0.01295 (16)	0.00281 (13)	0.00808 (13)	0.00104 (12)
C41'	0.0238 (7)	0.0306 (8)	0.0198 (7)	−0.0036 (6)	0.0064 (6)	0.0007 (6)
C5'	0.0206 (7)	0.0239 (7)	0.0174 (6)	−0.0068 (6)	0.0075 (5)	−0.0003 (5)
C6'	0.0253 (7)	0.0244 (7)	0.0150 (6)	−0.0067 (6)	0.0100 (5)	0.0019 (5)

Geometric parameters (Å, º)

C1—C2	1.3965 (18)	C7—C8	1.3341 (18)
C1—C6	1.4022 (18)	C7—H7	0.951 (15)
C1—C7	1.4659 (17)	C8—C1'	1.4619 (17)
C2—O2	1.3806 (15)	C8—H8	0.947 (17)
C2—C3	1.4026 (17)	C1'—C6'	1.3936 (18)
O2—C21	1.4342 (16)	C1'—C2'	1.3973 (17)
C21—H21A	1.000 (16)	C2'—C3'	1.3781 (18)
C21—H21B	0.985 (18)	C2'—H2'	0.952 (15)
C21—H21C	0.961 (16)	C3'—C4'	1.3894 (18)
C3—O3	1.3621 (15)	C3'—H3'	0.957 (15)
C3—C4	1.3848 (18)	C4'—C5'	1.3883 (17)
O3—C31	1.4264 (15)	C4'—S4'	1.7610 (13)
C31—H31A	1.004 (17)	S4'—C41'	1.7967 (15)
C31—H31B	0.963 (16)	C41'—H41A	0.954 (18)
C31—H31C	1.017 (17)	C41'—H41B	0.974 (18)
C4—C5	1.3899 (19)	C41'—H41C	0.979 (17)
C4—H4	0.943 (16)	C5'—C6'	1.3765 (18)
C5—C6	1.3742 (18)	C5'—H5'	0.938 (16)
C5—H5	0.953 (16)	C6'—H6'	0.956 (17)
C6—H6	0.944 (15)
C2—C1—C6	118.05 (11)	C8—C7—C1	125.94 (12)
C2—C1—C7	119.64 (11)	C8—C7—H7	119.9 (9)
C6—C1—C7	122.31 (11)	C1—C7—H7	114.2 (9)
O2—C2—C1	119.32 (11)	C7—C8—C1'	126.03 (12)
O2—C2—C3	119.70 (11)	C7—C8—H8	120.7 (10)
C1—C2—C3	120.86 (11)	C1'—C8—H8	113.3 (10)
C2—O2—C21	113.84 (10)	C6'—C1'—C2'	116.86 (11)
O2—C21—H21A	110.0 (9)	C6'—C1'—C8	122.94 (11)
O2—C21—H21B	105.3 (10)	C2'—C1'—C8	120.19 (11)
H21A—C21—H21B	107.8 (13)	C3'—C2'—C1'	121.66 (12)
O2—C21—H21C	111.6 (10)	C3'—C2'—H2'	119.3 (9)
H21A—C21—H21C	111.5 (13)	C1'—C2'—H2'	119.0 (9)
H21B—C21—H21C	110.3 (13)	C2'—C3'—C4'	120.32 (12)
O3—C3—C4	124.80 (11)	C2'—C3'—H3'	119.7 (9)
O3—C3—C2	115.30 (11)	C4'—C3'—H3'	120.0 (9)
C4—C3—C2	119.87 (11)	C5'—C4'—C3'	118.95 (12)
C3—O3—C31	117.33 (10)	C5'—C4'—S4'	123.48 (10)
O3—C31—H31A	110.1 (9)	C3'—C4'—S4'	117.57 (9)
O3—C31—H31B	105.8 (9)	C4'—S4'—C41'	103.04 (6)
H31A—C31—H31B	111.0 (12)	S4'—C41'—H41A	105.9 (10)
O3—C31—H31C	109.8 (9)	S4'—C41'—H41B	111.2 (11)
H31A—C31—H31C	109.4 (13)	H41A—C41'—H41B	107.8 (15)
H31B—C31—H31C	110.8 (13)	S4'—C41'—H41C	109.8 (10)
C3—C4—C5	119.33 (12)	H41A—C41'—H41C	110.3 (14)
C3—C4—H4	120.6 (9)	H41B—C41'—H41C	111.6 (14)
C5—C4—H4	120.0 (9)	C6'—C5'—C4'	120.09 (12)
C6—C5—C4	120.98 (12)	C6'—C5'—H5'	118.2 (10)
C6—C5—H5	119.1 (9)	C4'—C5'—H5'	121.7 (10)
C4—C5—H5	119.9 (9)	C5'—C6'—C1'	122.09 (12)
C5—C6—C1	120.87 (12)	C5'—C6'—H6'	119.1 (10)
C5—C6—H6	119.8 (9)	C1'—C6'—H6'	118.8 (10)
C1—C6—H6	119.3 (9)
C6—C1—C2—O2	−177.03 (11)	C2—C1—C7—C8	−175.08 (12)
C7—C1—C2—O2	4.00 (17)	C6—C1—C7—C8	6.0 (2)
C6—C1—C2—C3	−1.00 (18)	C1—C7—C8—C1'	−176.55 (11)
C7—C1—C2—C3	−179.97 (11)	C7—C8—C1'—C6'	4.8 (2)
C1—C2—O2—C21	−114.23 (13)	C7—C8—C1'—C2'	−176.29 (12)
C3—C2—O2—C21	69.70 (14)	C6'—C1'—C2'—C3'	−0.81 (19)
O2—C2—C3—O3	0.25 (16)	C8—C1'—C2'—C3'	−179.82 (11)
C1—C2—C3—O3	−175.76 (11)	C1'—C2'—C3'—C4'	−0.69 (19)
O2—C2—C3—C4	178.37 (11)	C2'—C3'—C4'—C5'	1.31 (19)
C1—C2—C3—C4	2.36 (18)	C2'—C3'—C4'—S4'	−178.13 (10)
C4—C3—O3—C31	5.83 (18)	C5'—C4'—S4'—C41'	14.07 (13)
C2—C3—O3—C31	−176.15 (10)	C3'—C4'—S4'—C41'	−166.53 (10)
O3—C3—C4—C5	176.04 (11)	C3'—C4'—C5'—C6'	−0.41 (19)
C2—C3—C4—C5	−1.90 (18)	S4'—C4'—C5'—C6'	178.99 (10)
C3—C4—C5—C6	0.12 (19)	C4'—C5'—C6'—C1'	−1.1 (2)
C4—C5—C6—C1	1.24 (19)	C2'—C1'—C6'—C5'	1.7 (2)
C2—C1—C6—C5	−0.79 (18)	C8—C1'—C6'—C5'	−179.29 (12)
C7—C1—C6—C5	178.15 (11)

1-[(E)-2-(2,5-Diethoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene (4)

Crystal data

C17H18O2S	Dx = 1.284 Mg m^−3
Mr = 286.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 21992 reflections
a = 18.4026 (2) Å	θ = 3.5–52.5°
b = 10.90882 (15) Å	µ = 0.22 mm^−1
c = 7.37881 (9) Å	T = 100 K
V = 1481.30 (3) Å^3	Prism, colourless
Z = 4	0.3 × 0.25 × 0.2 mm
F(000) = 608

Data collection

Rigaku OD Xcalibur Eos diffractometer	3587 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	3533 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.1544 pixels mm^-1	θmax = 28.0°, θmin = 2.9°
ω scans	h = −24→24
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −14→14
Tmin = 0.983, Tmax = 1.000	l = −9→9
27179 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0405P)^2 + 0.1865P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.060	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.26 e Å^−3
3587 reflections	Δρmin = −0.12 e Å^−3
253 parameters	Absolute structure: Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.007 (15)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.55026 (7)	0.78259 (12)	0.79729 (18)	0.0134 (2)
C2	0.59297 (7)	0.83654 (11)	0.9340 (2)	0.0150 (3)
O2	0.66614 (5)	0.81187 (10)	0.92580 (18)	0.0193 (2)
C21	0.70647 (9)	0.83199 (15)	1.0881 (2)	0.0220 (3)
H21A	0.7120 (11)	0.9216 (19)	1.108 (3)	0.024 (5)*
H21B	0.6844 (13)	0.797 (2)	1.190 (3)	0.027 (5)*
H21C	0.7530 (13)	0.795 (2)	1.066 (3)	0.031 (5)*
C3	0.56115 (8)	0.90982 (13)	1.0654 (2)	0.0183 (3)
H3	0.5896 (11)	0.9493 (19)	1.151 (3)	0.023 (5)*
C4	0.48616 (8)	0.92908 (12)	1.0663 (2)	0.0183 (3)
H4	0.4669 (10)	0.9773 (18)	1.155 (3)	0.020 (5)*
C5	0.44346 (7)	0.87544 (12)	0.9331 (2)	0.0157 (3)
O5	0.36918 (5)	0.88816 (9)	0.92010 (17)	0.0210 (2)
C51	0.33521 (9)	0.96531 (16)	1.0506 (3)	0.0257 (3)
H51A	0.2857 (13)	0.964 (2)	1.019 (4)	0.033 (6)*
H51B	0.3427 (12)	0.937 (2)	1.165 (4)	0.032 (6)*
H51C	0.3529 (12)	1.049 (2)	1.034 (3)	0.024 (5)*
C6	0.47558 (7)	0.80296 (12)	0.8002 (2)	0.0144 (2)
H6	0.4454 (12)	0.768 (2)	0.718 (3)	0.027 (5)*
C7	0.58401 (7)	0.70371 (12)	0.65996 (19)	0.0138 (2)
H7	0.6278 (11)	0.6670 (17)	0.688 (3)	0.017 (5)*
C8	0.55592 (7)	0.68438 (12)	0.4950 (2)	0.0145 (2)
H8	0.5135 (10)	0.7270 (17)	0.459 (3)	0.017 (4)*
C1'	0.58378 (7)	0.59889 (12)	0.35834 (18)	0.0134 (2)
C2'	0.55287 (7)	0.59916 (12)	0.1848 (2)	0.0146 (2)
H2'	0.5150 (12)	0.6552 (18)	0.160 (3)	0.021 (5)*
C3'	0.57660 (7)	0.51901 (12)	0.05134 (19)	0.0149 (3)
H3'	0.5562 (10)	0.5212 (16)	−0.063 (3)	0.016 (4)*
C4'	0.63210 (7)	0.43556 (12)	0.08853 (19)	0.0142 (3)
S4'	0.65633 (2)	0.33466 (3)	−0.08795 (6)	0.01937 (9)
C41'	0.71756 (9)	0.22901 (15)	0.0205 (2)	0.0229 (3)
H41A	0.7314 (12)	0.170 (2)	−0.071 (4)	0.034 (6)*
H41B	0.7631 (13)	0.268 (2)	0.063 (4)	0.034 (6)*
H41C	0.6923 (12)	0.1863 (19)	0.119 (3)	0.026 (5)*
C5'	0.66359 (8)	0.43384 (13)	0.2607 (2)	0.0166 (3)
H5'	0.7022 (11)	0.3804 (18)	0.286 (3)	0.019 (4)*
C6'	0.63911 (7)	0.51372 (12)	0.3938 (2)	0.0163 (3)
H6'	0.6607 (10)	0.5084 (19)	0.511 (3)	0.015 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0156 (6)	0.0123 (5)	0.0122 (6)	0.0000 (4)	0.0005 (5)	0.0002 (4)
C2	0.0148 (6)	0.0150 (6)	0.0153 (7)	−0.0009 (4)	−0.0014 (5)	−0.0006 (5)
O2	0.0136 (4)	0.0280 (5)	0.0164 (5)	0.0005 (4)	−0.0036 (4)	−0.0041 (5)
C21	0.0176 (7)	0.0317 (8)	0.0166 (7)	−0.0034 (6)	−0.0043 (5)	0.0008 (6)
C3	0.0204 (7)	0.0177 (6)	0.0168 (7)	−0.0016 (5)	−0.0021 (5)	−0.0044 (5)
C4	0.0217 (7)	0.0157 (6)	0.0176 (6)	0.0010 (5)	0.0017 (5)	−0.0040 (5)
C5	0.0148 (5)	0.0142 (5)	0.0182 (7)	0.0002 (4)	0.0018 (5)	0.0001 (5)
O5	0.0146 (4)	0.0233 (5)	0.0251 (5)	0.0029 (3)	0.0009 (5)	−0.0067 (5)
C51	0.0195 (7)	0.0281 (8)	0.0294 (9)	0.0048 (6)	0.0052 (6)	−0.0075 (7)
C6	0.0149 (6)	0.0131 (5)	0.0153 (6)	−0.0016 (5)	−0.0005 (5)	−0.0012 (5)
C7	0.0125 (6)	0.0140 (6)	0.0149 (6)	−0.0004 (5)	0.0007 (5)	−0.0003 (5)
C8	0.0145 (6)	0.0143 (6)	0.0148 (6)	0.0006 (5)	0.0005 (5)	−0.0005 (5)
C1'	0.0131 (5)	0.0136 (5)	0.0136 (6)	−0.0019 (4)	0.0004 (4)	0.0000 (4)
C2'	0.0143 (6)	0.0140 (6)	0.0154 (6)	−0.0001 (5)	−0.0004 (5)	0.0018 (5)
C3'	0.0162 (6)	0.0162 (6)	0.0124 (6)	−0.0027 (5)	−0.0006 (5)	0.0003 (5)
C4'	0.0135 (6)	0.0152 (5)	0.0140 (6)	−0.0026 (5)	0.0030 (5)	−0.0022 (5)
S4'	0.01985 (16)	0.02331 (16)	0.01493 (16)	0.00330 (11)	0.00204 (14)	−0.00489 (15)
C41'	0.0235 (7)	0.0218 (7)	0.0233 (7)	0.0055 (6)	0.0029 (6)	−0.0032 (6)
C5'	0.0149 (6)	0.0177 (6)	0.0172 (6)	0.0025 (5)	−0.0017 (5)	−0.0011 (5)
C6'	0.0153 (5)	0.0183 (6)	0.0152 (6)	0.0009 (4)	−0.0027 (5)	−0.0006 (5)

Geometric parameters (Å, º)

C1—C6	1.3923 (18)	C7—C8	1.339 (2)
C1—C2	1.4075 (19)	C7—H7	0.92 (2)
C1—C7	1.4673 (18)	C8—C1'	1.4659 (19)
C2—O2	1.3745 (16)	C8—H8	0.947 (19)
C2—C3	1.387 (2)	C1'—C2'	1.4011 (19)
O2—C21	1.4261 (18)	C1'—C6'	1.4032 (18)
C21—H21A	0.99 (2)	C2'—C3'	1.3875 (19)
C21—H21B	0.94 (2)	C2'—H2'	0.94 (2)
C21—H21C	0.96 (2)	C3'—C4'	1.3954 (19)
C3—C4	1.396 (2)	C3'—H3'	0.92 (2)
C3—H3	0.93 (2)	C4'—C5'	1.396 (2)
C4—C5	1.388 (2)	C4'—S4'	1.7623 (14)
C4—H4	0.91 (2)	S4'—C41'	1.7996 (16)
C5—O5	1.3772 (15)	C41'—H41A	0.97 (3)
C5—C6	1.3914 (19)	C41'—H41B	0.99 (2)
O5—C51	1.4234 (19)	C41'—H41C	0.98 (2)
C51—H51A	0.94 (2)	C5'—C6'	1.388 (2)
C51—H51B	0.91 (3)	C5'—H5'	0.94 (2)
C51—H51C	0.98 (2)	C6'—H6'	0.95 (2)
C6—H6	0.91 (2)
C6—C1—C2	118.26 (12)	C8—C7—C1	123.83 (13)
C6—C1—C7	121.47 (12)	C8—C7—H7	118.0 (13)
C2—C1—C7	120.24 (12)	C1—C7—H7	118.1 (13)
O2—C2—C3	123.87 (13)	C7—C8—C1'	126.18 (13)
O2—C2—C1	115.71 (13)	C7—C8—H8	119.9 (12)
C3—C2—C1	120.43 (12)	C1'—C8—H8	113.9 (12)
C2—O2—C21	116.29 (13)	C2'—C1'—C6'	117.82 (13)
O2—C21—H21A	109.1 (13)	C2'—C1'—C8	119.02 (12)
O2—C21—H21B	112.5 (14)	C6'—C1'—C8	123.14 (13)
H21A—C21—H21B	109.5 (19)	C3'—C2'—C1'	121.30 (12)
O2—C21—H21C	105.0 (15)	C3'—C2'—H2'	120.2 (13)
H21A—C21—H21C	110.5 (17)	C1'—C2'—H2'	118.5 (13)
H21B—C21—H21C	110 (2)	C2'—C3'—C4'	120.13 (13)
C2—C3—C4	120.50 (13)	C2'—C3'—H3'	120.2 (12)
C2—C3—H3	120.5 (13)	C4'—C3'—H3'	119.7 (12)
C4—C3—H3	118.9 (13)	C3'—C4'—C5'	119.43 (12)
C5—C4—C3	119.53 (13)	C3'—C4'—S4'	116.57 (11)
C5—C4—H4	122.2 (12)	C5'—C4'—S4'	123.98 (11)
C3—C4—H4	118.3 (12)	C4'—S4'—C41'	103.29 (7)
O5—C5—C4	124.66 (13)	S4'—C41'—H41A	106.4 (16)
O5—C5—C6	115.46 (12)	S4'—C41'—H41B	113.6 (13)
C4—C5—C6	119.88 (12)	H41A—C41'—H41B	106.5 (19)
C5—O5—C51	116.65 (12)	S4'—C41'—H41C	109.7 (13)
O5—C51—H51A	104.2 (15)	H41A—C41'—H41C	108.9 (19)
O5—C51—H51B	111.3 (15)	H41B—C41'—H41C	111.4 (19)
H51A—C51—H51B	112 (2)	C6'—C5'—C4'	120.04 (13)
O5—C51—H51C	108.9 (13)	C6'—C5'—H5'	119.9 (13)
H51A—C51—H51C	108.0 (19)	C4'—C5'—H5'	120.1 (13)
H51B—C51—H51C	112 (2)	C5'—C6'—C1'	121.26 (14)
C5—C6—C1	121.39 (13)	C5'—C6'—H6'	118.0 (12)
C5—C6—H6	116.9 (14)	C1'—C6'—H6'	120.7 (12)
C1—C6—H6	121.7 (14)
C6—C1—C2—O2	179.10 (12)	C6—C1—C7—C8	26.8 (2)
C7—C1—C2—O2	1.17 (19)	C2—C1—C7—C8	−155.35 (14)
C6—C1—C2—C3	−1.2 (2)	C1—C7—C8—C1'	−174.48 (13)
C7—C1—C2—C3	−179.14 (13)	C7—C8—C1'—C2'	−173.07 (13)
C3—C2—O2—C21	19.15 (19)	C7—C8—C1'—C6'	8.6 (2)
C1—C2—O2—C21	−161.18 (13)	C6'—C1'—C2'—C3'	−0.75 (19)
O2—C2—C3—C4	−179.02 (13)	C8—C1'—C2'—C3'	−179.15 (12)
C1—C2—C3—C4	1.3 (2)	C1'—C2'—C3'—C4'	0.3 (2)
C2—C3—C4—C5	−0.7 (2)	C2'—C3'—C4'—C5'	−0.23 (19)
C3—C4—C5—O5	−179.85 (13)	C2'—C3'—C4'—S4'	178.10 (10)
C3—C4—C5—C6	0.1 (2)	C3'—C4'—S4'—C41'	−171.46 (11)
C4—C5—O5—C51	2.1 (2)	C5'—C4'—S4'—C41'	6.79 (14)
C6—C5—O5—C51	−177.87 (13)	C3'—C4'—C5'—C6'	0.7 (2)
O5—C5—C6—C1	179.95 (12)	S4'—C4'—C5'—C6'	−177.47 (11)
C4—C5—C6—C1	0.0 (2)	C4'—C5'—C6'—C1'	−1.3 (2)
C2—C1—C6—C5	0.5 (2)	C2'—C1'—C6'—C5'	1.3 (2)
C7—C1—C6—C5	178.46 (12)	C8—C1'—C6'—C5'	179.59 (13)

1-[(E)-2-(3,5-Dimethoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene (5)

Crystal data

C17H18O2S	F(000) = 1216
Mr = 286.37	Dx = 1.294 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 7.22965 (6) Å	Cell parameters from 23674 reflections
b = 37.4539 (3) Å	θ = 3.5–76.2°
c = 10.85314 (10) Å	µ = 1.94 mm^−1
β = 90.0541 (7)°	T = 130 K
V = 2938.80 (4) Å^3	Plate, colourless
Z = 8	0.35 × 0.3 × 0.08 mm

Data collection

Rigaku OD SuperNova Single source diffractometer with an Atlas detector	6097 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	5945 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.044
Detector resolution: 10.5384 pixels mm^-1	θmax = 76.6°, θmin = 4.2°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −46→46
Tmin = 0.488, Tmax = 1.000	l = 0→13
34336 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0397P)^2 + 2.084P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.002
6097 reflections	Δρmax = 0.31 e Å^−3
368 parameters	Δρmin = −0.28 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
C1A	0.7039 (2)	0.37569 (5)	0.56057 (17)	0.0270 (4)
C2A	0.6814 (3)	0.40164 (5)	0.65285 (17)	0.0299 (4)
H2A	0.6906	0.3952	0.7373	0.036*
C3A	0.6457 (3)	0.43671 (5)	0.62001 (18)	0.0303 (4)
O3A	0.6203 (2)	0.46388 (4)	0.70261 (14)	0.0401 (3)
C31A	0.6173 (3)	0.45458 (6)	0.83023 (19)	0.0385 (5)
H31A	0.5178	0.4373	0.8452	0.058*
H31B	0.5957	0.4761	0.8797	0.058*
H31C	0.7362	0.4439	0.8534	0.058*
C4A	0.6333 (3)	0.44696 (5)	0.49653 (18)	0.0294 (4)
H4A	0.6098	0.4711	0.4748	0.035*
C5A	0.6560 (3)	0.42095 (5)	0.40601 (17)	0.0288 (4)
O5A	0.6449 (2)	0.42750 (4)	0.28210 (13)	0.0389 (3)
C51A	0.6110 (4)	0.46330 (6)	0.2438 (2)	0.0486 (6)
H51A	0.6078	0.4644	0.1536	0.073*
H51B	0.7100	0.4788	0.2746	0.073*
H51C	0.4921	0.4714	0.2770	0.073*
C6A	0.6920 (3)	0.38564 (5)	0.43743 (17)	0.0290 (4)
H6A	0.7085	0.3683	0.3746	0.035*
C7A	0.7359 (3)	0.33827 (5)	0.59656 (17)	0.0284 (4)
H7A	0.7787	0.3338	0.6779	0.034*
C8A	0.7092 (2)	0.31009 (5)	0.52316 (16)	0.0248 (3)
H8A	0.6662	0.3151	0.4423	0.030*
C1'A	0.7386 (2)	0.27235 (5)	0.55275 (15)	0.0216 (3)
C2'A	0.6782 (2)	0.24655 (5)	0.46896 (15)	0.0227 (3)
H2'A	0.6197	0.2541	0.3950	0.027*
C3'A	0.7007 (2)	0.21036 (5)	0.48998 (15)	0.0231 (3)
H3'A	0.6586	0.1935	0.4309	0.028*
C4'A	0.7853 (2)	0.19880 (5)	0.59820 (15)	0.0226 (3)
S4'A	0.82874 (7)	0.15381 (2)	0.63515 (4)	0.02918 (11)
C41A	0.6874 (4)	0.12965 (6)	0.5287 (2)	0.0455 (5)
H41A	0.7382	0.1322	0.4454	0.068*
H41B	0.5613	0.1392	0.5305	0.068*
H41C	0.6853	0.1044	0.5517	0.068*
C5'A	0.8452 (2)	0.22429 (5)	0.68384 (15)	0.0239 (3)
H5'A	0.9014	0.2167	0.7585	0.029*
C6'A	0.8238 (2)	0.26032 (5)	0.66125 (15)	0.0236 (3)
H6'A	0.8673	0.2772	0.7199	0.028*
C1B	0.8128 (2)	0.61189 (5)	0.17709 (17)	0.0270 (4)
C2B	0.8302 (3)	0.58929 (5)	0.27910 (17)	0.0282 (4)
H2B	0.8122	0.5984	0.3599	0.034*
C3B	0.8738 (2)	0.55353 (5)	0.26243 (17)	0.0280 (4)
O3B	0.8981 (2)	0.52970 (4)	0.35687 (13)	0.0347 (3)
C31B	0.8748 (3)	0.54303 (6)	0.47962 (18)	0.0345 (4)
H31D	0.7498	0.5528	0.4887	0.052*
H31E	0.9659	0.5619	0.4954	0.052*
H31F	0.8927	0.5235	0.5387	0.052*
C4B	0.8964 (3)	0.53968 (5)	0.14431 (18)	0.0305 (4)
H4B	0.9259	0.5152	0.1329	0.037*
C5B	0.8752 (3)	0.56214 (5)	0.04341 (17)	0.0296 (4)
O5B	0.8991 (2)	0.54572 (4)	−0.06869 (13)	0.0407 (4)
C51B	0.8750 (3)	0.56676 (6)	−0.17653 (19)	0.0425 (5)
H51D	0.8937	0.5518	−0.2496	0.064*
H51E	0.9653	0.5863	−0.1766	0.064*
H51F	0.7496	0.5767	−0.1777	0.064*
C6B	0.8343 (3)	0.59812 (5)	0.05774 (17)	0.0293 (4)
H6B	0.8212	0.6132	−0.0122	0.035*
C7B	0.7741 (3)	0.64976 (5)	0.20076 (17)	0.0294 (4)
H7B	0.7283	0.6556	0.2803	0.035*
C8B	0.7965 (2)	0.67686 (5)	0.12215 (16)	0.0257 (4)
H8B	0.8376	0.6710	0.0415	0.031*
C1'B	0.7639 (2)	0.71477 (5)	0.14851 (15)	0.0225 (3)
C2'B	0.8241 (2)	0.74049 (5)	0.06479 (15)	0.0239 (3)
H2'B	0.8842	0.7329	−0.0085	0.029*
C3'B	0.7996 (2)	0.77673 (5)	0.08451 (15)	0.0236 (3)
H3'B	0.8424	0.7935	0.0255	0.028*
C4'B	0.7116 (2)	0.78835 (5)	0.19150 (15)	0.0226 (3)
S4'B	0.67169 (7)	0.83348 (2)	0.22976 (4)	0.03085 (11)
C41B	0.7674 (3)	0.85740 (6)	0.1014 (2)	0.0393 (5)
H41D	0.7064	0.8497	0.0253	0.059*
H41E	0.9003	0.8525	0.0958	0.059*
H41F	0.7477	0.8831	0.1130	0.059*
C5'B	0.6486 (2)	0.76297 (5)	0.27640 (15)	0.0232 (3)
H5'B	0.5880	0.7706	0.3494	0.028*
C6'B	0.6734 (2)	0.72696 (5)	0.25527 (15)	0.0241 (3)
H6'B	0.6288	0.7102	0.3137	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0224 (8)	0.0293 (9)	0.0293 (9)	−0.0010 (7)	0.0019 (7)	−0.0017 (7)
C2A	0.0281 (9)	0.0338 (10)	0.0277 (9)	0.0009 (7)	0.0030 (7)	−0.0036 (7)
C3A	0.0239 (9)	0.0325 (9)	0.0345 (10)	0.0010 (7)	0.0032 (7)	−0.0070 (8)
O3A	0.0520 (9)	0.0328 (7)	0.0355 (8)	0.0053 (6)	0.0056 (7)	−0.0081 (6)
C31A	0.0397 (11)	0.0420 (11)	0.0337 (10)	0.0040 (9)	0.0016 (8)	−0.0090 (9)
C4A	0.0261 (9)	0.0267 (9)	0.0354 (10)	−0.0015 (7)	0.0020 (7)	−0.0010 (7)
C5A	0.0264 (9)	0.0307 (9)	0.0292 (9)	−0.0034 (7)	0.0022 (7)	0.0003 (7)
O5A	0.0579 (10)	0.0282 (7)	0.0307 (7)	−0.0003 (6)	0.0000 (7)	0.0027 (5)
C51A	0.0777 (18)	0.0294 (10)	0.0385 (12)	−0.0040 (11)	−0.0006 (11)	0.0061 (9)
C6A	0.0292 (9)	0.0287 (9)	0.0292 (9)	−0.0018 (7)	0.0024 (7)	−0.0032 (7)
C7A	0.0268 (9)	0.0333 (10)	0.0251 (9)	0.0017 (7)	0.0012 (7)	0.0001 (7)
C8A	0.0184 (8)	0.0317 (9)	0.0244 (8)	0.0000 (7)	0.0023 (6)	0.0015 (7)
C1'A	0.0140 (7)	0.0306 (9)	0.0203 (8)	0.0000 (6)	0.0038 (6)	−0.0007 (6)
C2'A	0.0175 (7)	0.0333 (9)	0.0174 (7)	0.0007 (7)	0.0013 (6)	0.0001 (6)
C3'A	0.0184 (8)	0.0312 (9)	0.0197 (8)	−0.0009 (6)	0.0024 (6)	−0.0015 (6)
C4'A	0.0169 (8)	0.0296 (8)	0.0214 (8)	0.0023 (6)	0.0043 (6)	0.0012 (6)
S4'A	0.0295 (2)	0.0301 (2)	0.0279 (2)	0.00533 (17)	0.00112 (17)	0.00452 (17)
C41A	0.0576 (14)	0.0297 (10)	0.0493 (13)	−0.0004 (10)	−0.0064 (11)	0.0004 (9)
C5'A	0.0152 (7)	0.0373 (9)	0.0194 (8)	0.0029 (6)	−0.0002 (6)	0.0013 (7)
C6'A	0.0163 (7)	0.0330 (9)	0.0214 (8)	−0.0001 (6)	0.0013 (6)	−0.0041 (6)
C1B	0.0233 (8)	0.0308 (9)	0.0269 (9)	−0.0010 (7)	0.0005 (7)	−0.0003 (7)
C2B	0.0261 (9)	0.0327 (9)	0.0256 (9)	−0.0009 (7)	−0.0001 (7)	−0.0011 (7)
C3B	0.0242 (9)	0.0308 (9)	0.0289 (9)	−0.0015 (7)	−0.0007 (7)	0.0030 (7)
O3B	0.0433 (8)	0.0315 (7)	0.0292 (7)	0.0045 (6)	−0.0019 (6)	0.0022 (5)
C31B	0.0350 (10)	0.0402 (11)	0.0284 (9)	0.0064 (8)	0.0007 (8)	0.0033 (8)
C4B	0.0301 (9)	0.0273 (9)	0.0340 (10)	−0.0003 (7)	0.0021 (8)	−0.0015 (7)
C5B	0.0273 (9)	0.0344 (10)	0.0271 (9)	−0.0021 (7)	0.0028 (7)	−0.0037 (7)
O5B	0.0592 (10)	0.0348 (7)	0.0282 (7)	0.0024 (7)	0.0060 (6)	−0.0049 (6)
C51B	0.0566 (14)	0.0445 (12)	0.0264 (10)	−0.0071 (10)	0.0039 (9)	−0.0029 (8)
C6B	0.0280 (9)	0.0312 (9)	0.0286 (9)	−0.0023 (7)	0.0027 (7)	0.0002 (7)
C7B	0.0315 (10)	0.0324 (10)	0.0242 (9)	0.0024 (7)	0.0018 (7)	−0.0012 (7)
C8B	0.0198 (8)	0.0334 (9)	0.0239 (8)	0.0014 (7)	0.0014 (6)	−0.0013 (7)
C1'B	0.0151 (7)	0.0312 (9)	0.0212 (8)	0.0008 (6)	−0.0018 (6)	0.0006 (7)
C2'B	0.0177 (8)	0.0357 (9)	0.0182 (8)	0.0003 (7)	0.0017 (6)	−0.0010 (7)
C3'B	0.0170 (8)	0.0329 (9)	0.0209 (8)	−0.0012 (6)	0.0001 (6)	0.0023 (7)
C4'B	0.0161 (7)	0.0300 (9)	0.0217 (8)	−0.0001 (6)	−0.0033 (6)	−0.0009 (6)
S4'B	0.0321 (2)	0.0298 (2)	0.0307 (2)	0.00019 (18)	0.00351 (18)	−0.00404 (17)
C41B	0.0426 (11)	0.0309 (10)	0.0444 (12)	−0.0023 (9)	0.0083 (9)	0.0041 (9)
C5'B	0.0164 (8)	0.0368 (9)	0.0163 (7)	0.0025 (6)	0.0000 (6)	−0.0011 (6)
C6'B	0.0198 (8)	0.0334 (9)	0.0190 (8)	0.0009 (7)	−0.0002 (6)	0.0043 (6)

Geometric parameters (Å, º)

C1A—C6A	1.390 (3)	C1B—C2B	1.399 (3)
C1A—C2A	1.405 (2)	C1B—C6B	1.403 (3)
C1A—C7A	1.473 (3)	C1B—C7B	1.468 (3)
C2A—C3A	1.385 (3)	C2B—C3B	1.388 (3)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—O3A	1.369 (2)	C3B—O3B	1.370 (2)
C3A—C4A	1.397 (3)	C3B—C4B	1.393 (3)
O3A—C31A	1.428 (2)	O3B—C31B	1.433 (2)
C31A—H31A	0.9800	C31B—H31D	0.9800
C31A—H31B	0.9800	C31B—H31E	0.9800
C31A—H31C	0.9800	C31B—H31F	0.9800
C4A—C5A	1.393 (3)	C4B—C5B	1.389 (3)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—O5A	1.369 (2)	C5B—O5B	1.374 (2)
C5A—C6A	1.390 (3)	C5B—C6B	1.388 (3)
O5A—C51A	1.425 (2)	O5B—C51B	1.421 (3)
C51A—H51A	0.9800	C51B—H51D	0.9800
C51A—H51B	0.9800	C51B—H51E	0.9800
C51A—H51C	0.9800	C51B—H51F	0.9800
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.336 (3)	C7B—C8B	1.336 (3)
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C1'A	1.465 (2)	C8B—C1'B	1.467 (2)
C8A—H8A	0.9500	C8B—H8B	0.9500
C1'A—C2'A	1.396 (2)	C1'B—C2'B	1.394 (2)
C1'A—C6'A	1.403 (2)	C1'B—C6'B	1.407 (2)
C2'A—C3'A	1.384 (2)	C2'B—C3'B	1.386 (3)
C2'A—H2'A	0.9500	C2'B—H2'B	0.9500
C3'A—C4'A	1.393 (2)	C3'B—C4'B	1.394 (2)
C3'A—H3'A	0.9500	C3'B—H3'B	0.9500
C4'A—C5'A	1.401 (2)	C4'B—C5'B	1.400 (2)
C4'A—S4'A	1.7605 (18)	C4'B—S4'B	1.7646 (18)
S4'A—C41A	1.788 (2)	S4'B—C41B	1.795 (2)
C41A—H41A	0.9800	C41B—H41D	0.9800
C41A—H41B	0.9800	C41B—H41E	0.9800
C41A—H41C	0.9800	C41B—H41F	0.9800
C5'A—C6'A	1.380 (3)	C5'B—C6'B	1.380 (3)
C5'A—H5'A	0.9500	C5'B—H5'B	0.9500
C6'A—H6'A	0.9500	C6'B—H6'B	0.9500
C6A—C1A—C2A	119.52 (17)	C2B—C1B—C6B	119.86 (17)
C6A—C1A—C7A	121.31 (17)	C2B—C1B—C7B	117.59 (16)
C2A—C1A—C7A	119.16 (17)	C6B—C1B—C7B	122.55 (16)
C3A—C2A—C1A	119.61 (18)	C3B—C2B—C1B	120.07 (17)
C3A—C2A—H2A	120.2	C3B—C2B—H2B	120.0
C1A—C2A—H2A	120.2	C1B—C2B—H2B	120.0
O3A—C3A—C2A	124.17 (18)	O3B—C3B—C2B	124.05 (17)
O3A—C3A—C4A	114.54 (17)	O3B—C3B—C4B	115.53 (17)
C2A—C3A—C4A	121.29 (17)	C2B—C3B—C4B	120.42 (17)
C3A—O3A—C31A	117.12 (16)	C3B—O3B—C31B	116.97 (15)
O3A—C31A—H31A	109.5	O3B—C31B—H31D	109.5
O3A—C31A—H31B	109.5	O3B—C31B—H31E	109.5
H31A—C31A—H31B	109.5	H31D—C31B—H31E	109.5
O3A—C31A—H31C	109.5	O3B—C31B—H31F	109.5
H31A—C31A—H31C	109.5	H31D—C31B—H31F	109.5
H31B—C31A—H31C	109.5	H31E—C31B—H31F	109.5
C5A—C4A—C3A	118.47 (17)	C5B—C4B—C3B	119.14 (17)
C5A—C4A—H4A	120.8	C5B—C4B—H4B	120.4
C3A—C4A—H4A	120.8	C3B—C4B—H4B	120.4
O5A—C5A—C6A	114.97 (16)	O5B—C5B—C6B	124.09 (18)
O5A—C5A—C4A	124.08 (17)	O5B—C5B—C4B	114.39 (17)
C6A—C5A—C4A	120.95 (18)	C6B—C5B—C4B	121.52 (17)
C5A—O5A—C51A	117.69 (16)	C5B—O5B—C51B	117.74 (16)
O5A—C51A—H51A	109.5	O5B—C51B—H51D	109.5
O5A—C51A—H51B	109.5	O5B—C51B—H51E	109.5
H51A—C51A—H51B	109.5	H51D—C51B—H51E	109.5
O5A—C51A—H51C	109.5	O5B—C51B—H51F	109.5
H51A—C51A—H51C	109.5	H51D—C51B—H51F	109.5
H51B—C51A—H51C	109.5	H51E—C51B—H51F	109.5
C1A—C6A—C5A	120.16 (17)	C5B—C6B—C1B	118.95 (17)
C1A—C6A—H6A	119.9	C5B—C6B—H6B	120.5
C5A—C6A—H6A	119.9	C1B—C6B—H6B	120.5
C8A—C7A—C1A	124.79 (18)	C8B—C7B—C1B	126.79 (17)
C8A—C7A—H7A	117.6	C8B—C7B—H7B	116.6
C1A—C7A—H7A	117.6	C1B—C7B—H7B	116.6
C7A—C8A—C1'A	127.63 (17)	C7B—C8B—C1'B	126.22 (17)
C7A—C8A—H8A	116.2	C7B—C8B—H8B	116.9
C1'A—C8A—H8A	116.2	C1'B—C8B—H8B	116.9
C2'A—C1'A—C6'A	117.46 (16)	C2'B—C1'B—C6'B	117.26 (16)
C2'A—C1'A—C8A	118.68 (15)	C2'B—C1'B—C8B	119.40 (15)
C6'A—C1'A—C8A	123.87 (16)	C6'B—C1'B—C8B	123.34 (16)
C3'A—C2'A—C1'A	122.25 (16)	C3'B—C2'B—C1'B	122.41 (16)
C3'A—C2'A—H2'A	118.9	C3'B—C2'B—H2'B	118.8
C1'A—C2'A—H2'A	118.9	C1'B—C2'B—H2'B	118.8
C2'A—C3'A—C4'A	119.66 (16)	C2'B—C3'B—C4'B	119.54 (16)
C2'A—C3'A—H3'A	120.2	C2'B—C3'B—H3'B	120.2
C4'A—C3'A—H3'A	120.2	C4'B—C3'B—H3'B	120.2
C3'A—C4'A—C5'A	118.88 (16)	C3'B—C4'B—C5'B	119.03 (16)
C3'A—C4'A—S4'A	124.59 (14)	C3'B—C4'B—S4'B	124.75 (14)
C5'A—C4'A—S4'A	116.51 (13)	C5'B—C4'B—S4'B	116.22 (13)
C4'A—S4'A—C41A	103.63 (9)	C4'B—S4'B—C41B	103.42 (9)
S4'A—C41A—H41A	109.5	S4'B—C41B—H41D	109.5
S4'A—C41A—H41B	109.5	S4'B—C41B—H41E	109.5
H41A—C41A—H41B	109.5	H41D—C41B—H41E	109.5
S4'A—C41A—H41C	109.5	S4'B—C41B—H41F	109.5
H41A—C41A—H41C	109.5	H41D—C41B—H41F	109.5
H41B—C41A—H41C	109.5	H41E—C41B—H41F	109.5
C6'A—C5'A—C4'A	120.92 (16)	C6'B—C5'B—C4'B	120.77 (15)
C6'A—C5'A—H5'A	119.5	C6'B—C5'B—H5'B	119.6
C4'A—C5'A—H5'A	119.5	C4'B—C5'B—H5'B	119.6
C5'A—C6'A—C1'A	120.82 (16)	C5'B—C6'B—C1'B	120.98 (16)
C5'A—C6'A—H6'A	119.6	C5'B—C6'B—H6'B	119.5
C1'A—C6'A—H6'A	119.6	C1'B—C6'B—H6'B	119.5
C6A—C1A—C2A—C3A	0.7 (3)	C6B—C1B—C2B—C3B	1.8 (3)
C7A—C1A—C2A—C3A	−178.09 (17)	C7B—C1B—C2B—C3B	−177.51 (17)
C1A—C2A—C3A—O3A	179.50 (17)	C1B—C2B—C3B—O3B	178.35 (17)
C1A—C2A—C3A—C4A	−0.6 (3)	C1B—C2B—C3B—C4B	−1.5 (3)
C2A—C3A—O3A—C31A	−4.8 (3)	C2B—C3B—O3B—C31B	0.5 (3)
C4A—C3A—O3A—C31A	175.32 (17)	C4B—C3B—O3B—C31B	−179.64 (17)
O3A—C3A—C4A—C5A	−179.55 (17)	O3B—C3B—C4B—C5B	−179.66 (17)
C2A—C3A—C4A—C5A	0.6 (3)	C2B—C3B—C4B—C5B	0.2 (3)
C3A—C4A—C5A—O5A	179.20 (18)	C3B—C4B—C5B—O5B	−179.54 (17)
C3A—C4A—C5A—C6A	−0.6 (3)	C3B—C4B—C5B—C6B	0.8 (3)
C6A—C5A—O5A—C51A	−179.06 (19)	C6B—C5B—O5B—C51B	−1.9 (3)
C4A—C5A—O5A—C51A	1.1 (3)	C4B—C5B—O5B—C51B	178.48 (18)
C2A—C1A—C6A—C5A	−0.7 (3)	O5B—C5B—C6B—C1B	179.90 (18)
C7A—C1A—C6A—C5A	178.02 (17)	C4B—C5B—C6B—C1B	−0.5 (3)
O5A—C5A—C6A—C1A	−179.13 (17)	C2B—C1B—C6B—C5B	−0.8 (3)
C4A—C5A—C6A—C1A	0.7 (3)	C7B—C1B—C6B—C5B	178.44 (17)
C6A—C1A—C7A—C8A	−18.1 (3)	C2B—C1B—C7B—C8B	162.43 (19)
C2A—C1A—C7A—C8A	160.62 (18)	C6B—C1B—C7B—C8B	−16.8 (3)
C1A—C7A—C8A—C1'A	179.86 (16)	C1B—C7B—C8B—C1'B	−177.55 (17)
C7A—C8A—C1'A—C2'A	171.18 (17)	C7B—C8B—C1'B—C2'B	168.71 (18)
C7A—C8A—C1'A—C6'A	−8.6 (3)	C7B—C8B—C1'B—C6'B	−11.4 (3)
C6'A—C1'A—C2'A—C3'A	−0.2 (2)	C6'B—C1'B—C2'B—C3'B	0.8 (3)
C8A—C1'A—C2'A—C3'A	179.98 (15)	C8B—C1'B—C2'B—C3'B	−179.31 (15)
C1'A—C2'A—C3'A—C4'A	0.3 (2)	C1'B—C2'B—C3'B—C4'B	0.0 (3)
C2'A—C3'A—C4'A—C5'A	0.3 (2)	C2'B—C3'B—C4'B—C5'B	−0.5 (2)
C2'A—C3'A—C4'A—S4'A	−178.18 (13)	C2'B—C3'B—C4'B—S4'B	179.62 (13)
C3'A—C4'A—S4'A—C41A	−15.23 (18)	C3'B—C4'B—S4'B—C41B	0.42 (18)
C5'A—C4'A—S4'A—C41A	166.28 (14)	C5'B—C4'B—S4'B—C41B	−179.46 (14)
C3'A—C4'A—C5'A—C6'A	−1.0 (2)	C3'B—C4'B—C5'B—C6'B	0.3 (2)
S4'A—C4'A—C5'A—C6'A	177.60 (13)	S4'B—C4'B—C5'B—C6'B	−179.84 (13)
C4'A—C5'A—C6'A—C1'A	1.1 (2)	C4'B—C5'B—C6'B—C1'B	0.5 (3)
C2'A—C1'A—C6'A—C5'A	−0.5 (2)	C2'B—C1'B—C6'B—C5'B	−1.0 (2)
C8A—C1'A—C6'A—C5'A	179.31 (15)	C8B—C1'B—C6'B—C5'B	179.08 (16)

1-[(E)-2-(2,4-Dimethoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene (6)

Crystal data

C17H18O2S	Dx = 1.254 Mg m^−3
Mr = 286.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 986 reflections
a = 5.4341 (2) Å	θ = 3.9–24.0°
b = 13.3220 (5) Å	µ = 0.21 mm^−1
c = 20.9587 (12) Å	T = 295 K
V = 1517.26 (12) Å^3	Plate, colourless
Z = 4	0.4 × 0.3 × 0.1 mm
F(000) = 608

Data collection

Rigaku OD Xcalibur Eos diffractometer	2642 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1974 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 16.2413 pixels mm^-1	θmax = 27.1°, θmin = 3.3°
ω scans	h = −6→5
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −8→17
Tmin = 0.991, Tmax = 1.000	l = −11→26
3592 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.029P)^2 + 0.3156P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.092	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.19 e Å^−3
2642 reflections	Δρmin = −0.20 e Å^−3
184 parameters	Absolute structure: Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.02 (5)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.6262 (6)	0.3182 (3)	0.59157 (16)	0.0437 (9)
C2	0.7767 (6)	0.2995 (3)	0.64473 (17)	0.0433 (8)
O2	0.9464 (5)	0.37259 (17)	0.65771 (12)	0.0604 (7)
C21	1.1081 (7)	0.3574 (3)	0.71053 (19)	0.0649 (12)
H21A	1.2089	0.2995	0.7028	0.097*
H21B	1.0131	0.3472	0.7486	0.097*
H21C	1.2111	0.4154	0.7157	0.097*
C3	0.7494 (7)	0.2144 (3)	0.68113 (17)	0.0479 (9)
H3	0.8530	0.2033	0.7157	0.057*
C4	0.5676 (7)	0.1450 (2)	0.66635 (16)	0.0475 (9)
O4	0.5551 (5)	0.06377 (19)	0.70614 (12)	0.0651 (8)
C41	0.3423 (8)	0.0018 (3)	0.7025 (2)	0.0773 (14)
H41A	0.3416	−0.0333	0.6625	0.116*
H41B	0.1975	0.0428	0.7056	0.116*
H41C	0.3444	−0.0457	0.7369	0.116*
C5	0.4158 (7)	0.1600 (3)	0.61441 (17)	0.0526 (10)
H5	0.2940	0.1138	0.6041	0.063*
C6	0.4497 (7)	0.2460 (3)	0.57802 (16)	0.0528 (10)
H6	0.3489	0.2557	0.5427	0.063*
C7	0.6501 (7)	0.4107 (3)	0.55435 (17)	0.0472 (9)
H7	0.7838	0.4514	0.5642	0.057*
C8	0.5051 (8)	0.4429 (3)	0.50870 (16)	0.0514 (9)
H8	0.3745	0.4010	0.4980	0.062*
C1'	0.5234 (7)	0.5365 (2)	0.47251 (15)	0.0438 (8)
C2'	0.3458 (7)	0.5595 (3)	0.42745 (18)	0.0551 (10)
H2'	0.2186	0.5141	0.4204	0.066*
C3'	0.3505 (7)	0.6471 (3)	0.39273 (18)	0.0563 (10)
H3'	0.2278	0.6594	0.3628	0.068*
C4'	0.5352 (7)	0.7171 (3)	0.40170 (14)	0.0454 (9)
S4'	0.5214 (2)	0.82817 (7)	0.35645 (5)	0.0679 (3)
C41'	0.8150 (11)	0.8820 (4)	0.3650 (3)	0.134 (2)
H41D	0.8255	0.9415	0.3393	0.201*
H41E	0.9378	0.8348	0.3515	0.201*
H41F	0.8420	0.8991	0.4089	0.201*
C5'	0.7148 (7)	0.6953 (3)	0.44647 (17)	0.0511 (10)
H5'	0.8414	0.7409	0.4535	0.061*
C6'	0.7094 (7)	0.6071 (3)	0.48084 (17)	0.0507 (10)
H6'	0.8333	0.5945	0.5104	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.049 (2)	0.042 (2)	0.0391 (18)	−0.0013 (19)	0.0011 (17)	−0.0008 (17)
C2	0.0414 (19)	0.044 (2)	0.0448 (19)	0.0025 (18)	−0.0003 (19)	−0.0036 (19)
O2	0.0611 (17)	0.0550 (14)	0.0651 (16)	−0.0139 (14)	−0.0181 (14)	0.0111 (13)
C21	0.052 (2)	0.068 (3)	0.075 (3)	−0.010 (2)	−0.015 (2)	0.003 (2)
C3	0.050 (2)	0.049 (2)	0.045 (2)	0.001 (2)	−0.0118 (18)	0.0054 (18)
C4	0.054 (2)	0.042 (2)	0.0468 (19)	−0.0012 (18)	−0.0002 (19)	0.0000 (16)
O4	0.0689 (19)	0.0561 (15)	0.0702 (17)	−0.0142 (16)	−0.0136 (16)	0.0236 (14)
C41	0.072 (3)	0.069 (3)	0.091 (3)	−0.017 (3)	0.002 (3)	0.028 (3)
C5	0.058 (2)	0.045 (2)	0.055 (2)	−0.0099 (19)	−0.012 (2)	−0.0042 (19)
C6	0.064 (3)	0.053 (2)	0.0419 (18)	−0.002 (2)	−0.010 (2)	0.0019 (17)
C7	0.051 (2)	0.049 (2)	0.041 (2)	−0.0006 (18)	−0.0008 (19)	−0.0009 (18)
C8	0.053 (2)	0.050 (2)	0.0507 (19)	−0.005 (2)	−0.004 (2)	0.0012 (17)
C1'	0.048 (2)	0.044 (2)	0.0391 (17)	0.003 (2)	0.0030 (19)	−0.0015 (15)
C2'	0.052 (2)	0.053 (2)	0.060 (2)	−0.010 (2)	−0.008 (2)	0.004 (2)
C3'	0.058 (2)	0.064 (3)	0.048 (2)	0.003 (2)	−0.013 (2)	0.004 (2)
C4'	0.051 (2)	0.050 (2)	0.0354 (17)	0.004 (2)	0.0030 (18)	−0.0041 (15)
S4'	0.0853 (8)	0.0600 (6)	0.0582 (6)	0.0069 (7)	0.0027 (7)	0.0160 (5)
C41'	0.167 (5)	0.108 (4)	0.128 (5)	−0.080 (4)	−0.070 (4)	0.066 (4)
C5'	0.055 (2)	0.051 (2)	0.047 (2)	−0.012 (2)	0.000 (2)	0.0011 (19)
C6'	0.053 (2)	0.056 (2)	0.043 (2)	0.002 (2)	−0.0094 (19)	0.0041 (19)

Geometric parameters (Å, º)

C1—C6	1.387 (5)	C7—C8	1.312 (5)
C1—C2	1.404 (4)	C7—H7	0.9300
C1—C7	1.465 (5)	C8—C1'	1.463 (4)
C2—O2	1.368 (4)	C8—H8	0.9300
C2—C3	1.375 (5)	C1'—C2'	1.385 (5)
O2—C21	1.428 (4)	C1'—C6'	1.392 (5)
C21—H21A	0.9600	C2'—C3'	1.375 (5)
C21—H21B	0.9600	C2'—H2'	0.9300
C21—H21C	0.9600	C3'—C4'	1.383 (5)
C3—C4	1.388 (5)	C3'—H3'	0.9300
C3—H3	0.9300	C4'—C5'	1.385 (5)
C4—O4	1.368 (4)	C4'—S4'	1.759 (3)
C4—C5	1.380 (5)	S4'—C41'	1.758 (5)
O4—C41	1.422 (4)	C41'—H41D	0.9600
C41—H41A	0.9600	C41'—H41E	0.9600
C41—H41B	0.9600	C41'—H41F	0.9600
C41—H41C	0.9600	C5'—C6'	1.378 (5)
C5—C6	1.388 (5)	C5'—H5'	0.9300
C5—H5	0.9300	C6'—H6'	0.9300
C6—H6	0.9300
C6—C1—C2	116.3 (3)	C8—C7—C1	127.6 (3)
C6—C1—C7	122.4 (3)	C8—C7—H7	116.2
C2—C1—C7	121.3 (3)	C1—C7—H7	116.2
O2—C2—C3	123.3 (3)	C7—C8—C1'	128.0 (4)
O2—C2—C1	115.1 (3)	C7—C8—H8	116.0
C3—C2—C1	121.6 (3)	C1'—C8—H8	116.0
C2—O2—C21	117.9 (3)	C2'—C1'—C6'	116.2 (3)
O2—C21—H21A	109.5	C2'—C1'—C8	119.7 (4)
O2—C21—H21B	109.5	C6'—C1'—C8	124.1 (3)
H21A—C21—H21B	109.5	C3'—C2'—C1'	122.4 (4)
O2—C21—H21C	109.5	C3'—C2'—H2'	118.8
H21A—C21—H21C	109.5	C1'—C2'—H2'	118.8
H21B—C21—H21C	109.5	C2'—C3'—C4'	120.9 (3)
C2—C3—C4	120.1 (3)	C2'—C3'—H3'	119.5
C2—C3—H3	119.9	C4'—C3'—H3'	119.5
C4—C3—H3	119.9	C3'—C4'—C5'	117.5 (3)
O4—C4—C5	124.5 (3)	C3'—C4'—S4'	117.6 (3)
O4—C4—C3	115.2 (3)	C5'—C4'—S4'	124.9 (3)
C5—C4—C3	120.3 (3)	C41'—S4'—C4'	104.4 (2)
C4—O4—C41	117.8 (3)	S4'—C41'—H41D	109.5
O4—C41—H41A	109.5	S4'—C41'—H41E	109.5
O4—C41—H41B	109.5	H41D—C41'—H41E	109.5
H41A—C41—H41B	109.5	S4'—C41'—H41F	109.5
O4—C41—H41C	109.5	H41D—C41'—H41F	109.5
H41A—C41—H41C	109.5	H41E—C41'—H41F	109.5
H41B—C41—H41C	109.5	C6'—C5'—C4'	121.2 (3)
C4—C5—C6	118.3 (3)	C6'—C5'—H5'	119.4
C4—C5—H5	120.9	C4'—C5'—H5'	119.4
C6—C5—H5	120.9	C5'—C6'—C1'	121.7 (3)
C1—C6—C5	123.4 (3)	C5'—C6'—H6'	119.1
C1—C6—H6	118.3	C1'—C6'—H6'	119.1
C5—C6—H6	118.3
C6—C1—C2—O2	−178.9 (3)	C6—C1—C7—C8	6.2 (6)
C7—C1—C2—O2	−1.1 (5)	C2—C1—C7—C8	−171.5 (4)
C6—C1—C2—C3	−0.1 (5)	C1—C7—C8—C1'	178.1 (3)
C7—C1—C2—C3	177.7 (3)	C7—C8—C1'—C2'	−177.4 (4)
C3—C2—O2—C21	2.2 (5)	C7—C8—C1'—C6'	1.5 (6)
C1—C2—O2—C21	−179.0 (3)	C6'—C1'—C2'—C3'	−0.2 (5)
O2—C2—C3—C4	177.8 (3)	C8—C1'—C2'—C3'	178.8 (3)
C1—C2—C3—C4	−1.0 (5)	C1'—C2'—C3'—C4'	−0.3 (6)
C2—C3—C4—O4	−179.3 (3)	C2'—C3'—C4'—C5'	0.4 (5)
C2—C3—C4—C5	1.2 (5)	C2'—C3'—C4'—S4'	−178.5 (3)
C5—C4—O4—C41	−13.9 (5)	C3'—C4'—S4'—C41'	−165.7 (3)
C3—C4—O4—C41	166.5 (3)	C5'—C4'—S4'—C41'	15.5 (4)
O4—C4—C5—C6	−179.8 (3)	C3'—C4'—C5'—C6'	−0.1 (5)
C3—C4—C5—C6	−0.3 (5)	S4'—C4'—C5'—C6'	178.7 (3)
C2—C1—C6—C5	1.0 (5)	C4'—C5'—C6'—C1'	−0.4 (6)
C7—C1—C6—C5	−176.8 (3)	C2'—C1'—C6'—C5'	0.5 (5)
C4—C5—C6—C1	−0.8 (5)	C8—C1'—C6'—C5'	−178.5 (4)

1-[(E)-2-(2,4,5-Trimethoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene (7)

Crystal data

C18H20O3S	Dx = 1.308 Mg m^−3
Mr = 316.40	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, P212121	Cell parameters from 1643 reflections
a = 5.3187 (3) Å	θ = 3.3–24.3°
b = 8.3866 (7) Å	µ = 0.21 mm^−1
c = 36.019 (2) Å	T = 100 K
V = 1606.66 (18) Å^3	Plate, colourless
Z = 4	0.2 × 0.12 × 0.05 mm
F(000) = 672

Data collection

Rigaku OD Xcalibur Eos diffractometer	2811 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1687 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.093
Detector resolution: 16.1544 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −9→9
Tmin = 0.790, Tmax = 1.000	l = −42→41
8563 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.065	w = 1/[σ^2(Fo^2) + (0.010P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.095	(Δ/σ)max = 0.009
S = 0.86	Δρmax = 0.37 e Å^−3
2811 reflections	Δρmin = −0.31 e Å^−3
203 parameters	Absolute structure: Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.05 (18)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.5744 (10)	0.3860 (7)	0.63893 (13)	0.0145 (14)
C2	0.4038 (11)	0.4552 (7)	0.66334 (15)	0.0165 (14)
O2	0.2375 (7)	0.5636 (5)	0.64828 (9)	0.0230 (11)
C21	0.0502 (9)	0.6297 (7)	0.67222 (13)	0.0169 (14)
H21A	−0.0651	0.6960	0.6577	0.025*
H21B	0.1314	0.6952	0.6913	0.025*
H21C	−0.0441	0.5433	0.6841	0.025*
C3	0.4064 (9)	0.4170 (7)	0.70109 (14)	0.0155 (14)
H3	0.2875	0.4639	0.7175	0.019*
C4	0.5826 (10)	0.3109 (7)	0.71441 (15)	0.0137 (14)
O4	0.5971 (6)	0.2648 (4)	0.75102 (10)	0.0161 (10)
C41	0.3868 (10)	0.3076 (7)	0.77396 (14)	0.0219 (16)
H41A	0.2309	0.2708	0.7623	0.033*
H41B	0.3813	0.4237	0.7769	0.033*
H41C	0.4049	0.2575	0.7984	0.033*
C5	0.7575 (9)	0.2412 (7)	0.69055 (14)	0.0143 (14)
O5	0.9287 (6)	0.1402 (5)	0.70682 (9)	0.0186 (10)
C51	1.0977 (10)	0.0594 (7)	0.68248 (14)	0.0229 (16)
H51A	1.0015	−0.0015	0.6641	0.034*
H51B	1.2038	−0.0134	0.6969	0.034*
H51C	1.2039	0.1377	0.6697	0.034*
C6	0.7506 (10)	0.2793 (6)	0.65311 (14)	0.0149 (14)
H6	0.8688	0.2314	0.6368	0.018*
C7	0.5671 (10)	0.4317 (7)	0.59938 (14)	0.0184 (15)
H7	0.4226	0.4888	0.5914	0.022*
C8	0.7414 (10)	0.4017 (7)	0.57367 (13)	0.0188 (15)
H8	0.8848	0.3418	0.5809	0.023*
C1'	0.7260 (10)	0.4550 (7)	0.53494 (14)	0.0147 (14)
C2'	0.9111 (10)	0.4049 (7)	0.50968 (15)	0.0203 (15)
H2'	1.0422	0.3371	0.5182	0.024*
C3'	0.9080 (10)	0.4513 (7)	0.47283 (15)	0.0203 (15)
H3'	1.0330	0.4131	0.4562	0.024*
C4'	0.7225 (11)	0.5537 (7)	0.46014 (14)	0.0178 (14)
S4'	0.6962 (3)	0.6273 (2)	0.41440 (4)	0.0300 (5)
C41'	1.0044 (9)	0.5984 (8)	0.39544 (15)	0.036 (2)
H41D	1.0126	0.6458	0.3706	0.054*
H41E	1.0402	0.4840	0.3938	0.054*
H41F	1.1290	0.6495	0.4116	0.054*
C5'	0.5354 (9)	0.6062 (7)	0.48476 (14)	0.0185 (15)
H5'	0.4063	0.6756	0.4763	0.022*
C6'	0.5401 (10)	0.5562 (8)	0.52131 (15)	0.0216 (16)
H6'	0.4122	0.5921	0.5377	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.016 (3)	0.016 (4)	0.012 (3)	−0.001 (3)	0.000 (3)	−0.002 (3)
C2	0.019 (3)	0.011 (4)	0.019 (4)	0.001 (3)	0.000 (3)	0.003 (3)
O2	0.025 (2)	0.028 (3)	0.016 (2)	0.014 (2)	0.005 (2)	0.0032 (18)
C21	0.013 (3)	0.022 (4)	0.016 (3)	0.004 (3)	−0.003 (3)	0.002 (3)
C3	0.009 (3)	0.021 (4)	0.017 (3)	−0.001 (3)	0.001 (3)	−0.005 (3)
C4	0.020 (3)	0.012 (4)	0.009 (3)	0.001 (3)	0.003 (3)	−0.001 (2)
O4	0.015 (2)	0.022 (3)	0.010 (2)	0.0030 (19)	0.0015 (18)	0.0033 (18)
C41	0.026 (4)	0.025 (4)	0.015 (3)	0.003 (3)	0.003 (3)	0.002 (3)
C5	0.012 (3)	0.016 (4)	0.015 (3)	−0.003 (3)	−0.001 (3)	0.001 (3)
O5	0.014 (2)	0.022 (3)	0.020 (2)	0.006 (2)	0.0011 (18)	0.004 (2)
C51	0.021 (3)	0.021 (4)	0.027 (4)	0.012 (3)	0.003 (3)	0.000 (3)
C6	0.010 (3)	0.015 (4)	0.020 (3)	−0.003 (3)	0.002 (3)	−0.006 (3)
C7	0.017 (3)	0.022 (4)	0.016 (3)	0.003 (3)	−0.003 (3)	0.003 (3)
C8	0.020 (3)	0.020 (4)	0.017 (3)	0.004 (3)	−0.003 (3)	0.007 (3)
C1'	0.013 (3)	0.017 (4)	0.014 (3)	−0.003 (3)	0.004 (3)	−0.004 (3)
C2'	0.019 (3)	0.023 (4)	0.019 (3)	0.005 (3)	−0.007 (3)	0.002 (3)
C3'	0.014 (3)	0.025 (4)	0.022 (4)	−0.002 (3)	0.005 (3)	−0.007 (3)
C4'	0.020 (3)	0.019 (4)	0.015 (3)	−0.003 (3)	0.003 (3)	−0.003 (3)
S4'	0.0206 (8)	0.0534 (13)	0.0161 (8)	0.0021 (10)	0.0008 (8)	0.0066 (9)
C41'	0.026 (4)	0.062 (6)	0.020 (4)	0.005 (4)	0.008 (3)	0.006 (4)
C5'	0.015 (3)	0.024 (4)	0.017 (3)	0.002 (3)	−0.005 (3)	0.003 (3)
C6'	0.017 (3)	0.028 (5)	0.020 (4)	0.001 (3)	0.006 (3)	−0.006 (3)

Geometric parameters (Å, º)

C1—C2	1.391 (7)	C51—H51C	0.9800
C1—C6	1.393 (7)	C6—H6	0.9500
C1—C7	1.476 (6)	C7—C8	1.335 (6)
C2—O2	1.379 (6)	C7—H7	0.9500
C2—C3	1.397 (7)	C8—C1'	1.467 (6)
O2—C21	1.429 (5)	C8—H8	0.9500
C21—H21A	0.9800	C1'—C6'	1.392 (7)
C21—H21B	0.9800	C1'—C2'	1.405 (7)
C21—H21C	0.9800	C2'—C3'	1.383 (7)
C3—C4	1.379 (7)	C2'—H2'	0.9500
C3—H3	0.9500	C3'—C4'	1.385 (7)
C4—O4	1.376 (6)	C3'—H3'	0.9500
C4—C5	1.395 (7)	C4'—C5'	1.404 (7)
O4—C41	1.436 (5)	C4'—S4'	1.765 (5)
C41—H41A	0.9800	S4'—C41'	1.792 (5)
C41—H41B	0.9800	C41'—H41D	0.9800
C41—H41C	0.9800	C41'—H41E	0.9800
C5—O5	1.375 (6)	C41'—H41F	0.9800
C5—C6	1.386 (6)	C5'—C6'	1.382 (7)
O5—C51	1.427 (5)	C5'—H5'	0.9500
C51—H51A	0.9800	C6'—H6'	0.9500
C51—H51B	0.9800
C2—C1—C6	118.4 (5)	H51B—C51—H51C	109.5
C2—C1—C7	119.0 (5)	C5—C6—C1	121.5 (5)
C6—C1—C7	122.6 (5)	C5—C6—H6	119.3
O2—C2—C1	116.4 (5)	C1—C6—H6	119.3
O2—C2—C3	122.7 (5)	C8—C7—C1	127.0 (5)
C1—C2—C3	120.9 (5)	C8—C7—H7	116.5
C2—O2—C21	117.7 (4)	C1—C7—H7	116.5
O2—C21—H21A	109.5	C7—C8—C1'	124.3 (5)
O2—C21—H21B	109.5	C7—C8—H8	117.9
H21A—C21—H21B	109.5	C1'—C8—H8	117.9
O2—C21—H21C	109.5	C6'—C1'—C2'	116.9 (5)
H21A—C21—H21C	109.5	C6'—C1'—C8	124.1 (5)
H21B—C21—H21C	109.5	C2'—C1'—C8	119.0 (5)
C4—C3—C2	119.6 (5)	C3'—C2'—C1'	121.9 (5)
C4—C3—H3	120.2	C3'—C2'—H2'	119.0
C2—C3—H3	120.2	C1'—C2'—H2'	119.0
O4—C4—C3	123.6 (5)	C2'—C3'—C4'	120.0 (5)
O4—C4—C5	115.8 (5)	C2'—C3'—H3'	120.0
C3—C4—C5	120.6 (5)	C4'—C3'—H3'	120.0
C4—O4—C41	115.9 (4)	C3'—C4'—C5'	119.4 (5)
O4—C41—H41A	109.5	C3'—C4'—S4'	125.5 (4)
O4—C41—H41B	109.5	C5'—C4'—S4'	115.1 (4)
H41A—C41—H41B	109.5	C4'—S4'—C41'	103.6 (3)
O4—C41—H41C	109.5	S4'—C41'—H41D	109.5
H41A—C41—H41C	109.5	S4'—C41'—H41E	109.5
H41B—C41—H41C	109.5	H41D—C41'—H41E	109.5
O5—C5—C6	125.0 (5)	S4'—C41'—H41F	109.5
O5—C5—C4	115.9 (5)	H41D—C41'—H41F	109.5
C6—C5—C4	119.0 (5)	H41E—C41'—H41F	109.5
C5—O5—C51	116.6 (4)	C6'—C5'—C4'	119.6 (5)
O5—C51—H51A	109.5	C6'—C5'—H5'	120.2
O5—C51—H51B	109.5	C4'—C5'—H5'	120.2
H51A—C51—H51B	109.5	C5'—C6'—C1'	122.3 (5)
O5—C51—H51C	109.5	C5'—C6'—H6'	118.9
H51A—C51—H51C	109.5	C1'—C6'—H6'	118.9
C6—C1—C2—O2	178.2 (5)	C2—C1—C6—C5	0.2 (8)
C7—C1—C2—O2	0.0 (8)	C7—C1—C6—C5	178.4 (5)
C6—C1—C2—C3	−0.9 (8)	C2—C1—C7—C8	166.6 (6)
C7—C1—C2—C3	−179.1 (5)	C6—C1—C7—C8	−11.5 (9)
C1—C2—O2—C21	176.4 (5)	C1—C7—C8—C1'	−178.0 (5)
C3—C2—O2—C21	−4.6 (8)	C7—C8—C1'—C6'	6.5 (9)
O2—C2—C3—C4	−178.2 (5)	C7—C8—C1'—C2'	−174.8 (6)
C1—C2—C3—C4	0.8 (9)	C6'—C1'—C2'—C3'	−1.0 (9)
C2—C3—C4—O4	−179.1 (5)	C8—C1'—C2'—C3'	−179.8 (5)
C2—C3—C4—C5	−0.1 (9)	C1'—C2'—C3'—C4'	1.8 (9)
C3—C4—O4—C41	12.2 (7)	C2'—C3'—C4'—C5'	−1.6 (9)
C5—C4—O4—C41	−166.8 (5)	C2'—C3'—C4'—S4'	178.6 (5)
O4—C4—C5—O5	−2.4 (7)	C3'—C4'—S4'—C41'	−19.3 (6)
C3—C4—C5—O5	178.4 (5)	C5'—C4'—S4'—C41'	160.9 (5)
O4—C4—C5—C6	178.6 (5)	C3'—C4'—C5'—C6'	0.6 (9)
C3—C4—C5—C6	−0.5 (8)	S4'—C4'—C5'—C6'	−179.6 (5)
C6—C5—O5—C51	−5.3 (8)	C4'—C5'—C6'—C1'	0.2 (9)
C4—C5—O5—C51	175.8 (5)	C2'—C1'—C6'—C5'	−0.1 (9)
O5—C5—C6—C1	−178.4 (5)	C8—C1'—C6'—C5'	178.7 (5)
C4—C5—C6—C1	0.5 (8)

1-[(E)-2-(3,4,5-Trimethoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene (8)

Crystal data

C18H20O3S	F(000) = 1344
Mr = 316.40	Dx = 1.314 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.9270 (4) Å	Cell parameters from 4347 reflections
b = 7.2754 (3) Å	θ = 3.4–28.9°
c = 40.2818 (19) Å	µ = 0.21 mm^−1
β = 93.094 (4)°	T = 100 K
V = 3197.7 (2) Å^3	Prism, colourless
Z = 8	0.45 × 0.2 × 0.07 mm

Data collection

Rigaku OD Xcalibur Eos diffractometer	7403 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5810 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 16.1544 pixels mm^-1	θmax = 29.3°, θmin = 3.0°
ω scans	h = −14→11
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −9→9
Tmin = 0.784, Tmax = 1.000	l = −54→35
14744 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 1.4658P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
7403 reflections	Δρmax = 1.14 e Å^−3
405 parameters	Δρmin = −0.32 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1A	0.32347 (16)	0.1101 (3)	0.36336 (4)	0.0150 (4)
C2A	0.21929 (16)	0.0855 (3)	0.38112 (5)	0.0156 (4)
H2A	0.1405	0.0921	0.3700	0.019*
C3A	0.22963 (16)	0.0513 (3)	0.41504 (5)	0.0159 (4)
O3A	0.13277 (11)	0.0197 (2)	0.43436 (3)	0.0218 (3)
C31A	0.01356 (17)	0.0085 (3)	0.41835 (5)	0.0253 (5)
H31A	0.0144	−0.0799	0.4000	0.038*
H31B	−0.0107	0.1296	0.4096	0.038*
H31C	−0.0451	−0.0321	0.4344	0.038*
C4A	0.34488 (16)	0.0420 (3)	0.43173 (4)	0.0143 (4)
O4A	0.35464 (11)	−0.00736 (19)	0.46451 (3)	0.0174 (3)
C42A	0.37446 (19)	0.1443 (3)	0.48713 (5)	0.0241 (4)
H42A	0.4491	0.2101	0.4818	0.036*
H42B	0.3835	0.0978	0.5100	0.036*
H42C	0.3043	0.2282	0.4851	0.036*
C5A	0.44953 (16)	0.0672 (3)	0.41380 (4)	0.0147 (4)
O5A	0.55763 (11)	0.0481 (2)	0.43216 (3)	0.0192 (3)
C51A	0.66764 (16)	0.0534 (3)	0.41469 (5)	0.0203 (4)
H51A	0.6629	−0.0376	0.3967	0.030*
H51B	0.7377	0.0251	0.4301	0.030*
H51C	0.6780	0.1763	0.4053	0.030*
C6A	0.43980 (16)	0.1022 (3)	0.37986 (4)	0.0154 (4)
H6A	0.5114	0.1207	0.3679	0.019*
C7A	0.30779 (16)	0.1303 (3)	0.32703 (4)	0.0155 (4)
H7A	0.2277	0.1097	0.3174	0.019*
C8A	0.39382 (16)	0.1746 (3)	0.30629 (5)	0.0158 (4)
H8A	0.4717	0.2084	0.3160	0.019*
C1'A	0.38024 (16)	0.1762 (3)	0.26988 (4)	0.0140 (4)
C2'A	0.47394 (16)	0.2492 (3)	0.25149 (5)	0.0157 (4)
H2'A	0.5436	0.3021	0.2629	0.019*
C3'A	0.46784 (16)	0.2463 (3)	0.21734 (5)	0.0155 (4)
H3'A	0.5327	0.2977	0.2056	0.019*
C4'A	0.36746 (15)	0.1688 (3)	0.19976 (4)	0.0135 (4)
S4'A	0.37190 (4)	0.15985 (8)	0.15622 (2)	0.02039 (13)
C41A	0.21376 (17)	0.1311 (3)	0.14232 (5)	0.0212 (4)
H41A	0.2051	0.1481	0.1182	0.032*
H41B	0.1635	0.2223	0.1532	0.032*
H41C	0.1865	0.0072	0.1480	0.032*
C5'A	0.27219 (15)	0.0962 (3)	0.21752 (4)	0.0135 (4)
H5'A	0.2025	0.0441	0.2059	0.016*
C6'A	0.27907 (15)	0.1002 (3)	0.25202 (4)	0.0142 (4)
H6'A	0.2137	0.0502	0.2638	0.017*
C1B	0.24956 (17)	0.4361 (3)	0.61267 (4)	0.0154 (4)
C2B	0.13261 (17)	0.4710 (3)	0.59876 (5)	0.0170 (4)
H2B	0.0645	0.4706	0.6125	0.020*
C3B	0.11494 (16)	0.5063 (3)	0.56498 (5)	0.0165 (4)
O3B	0.00344 (11)	0.5411 (2)	0.54931 (3)	0.0219 (3)
C31B	−0.10282 (16)	0.5127 (3)	0.56762 (5)	0.0213 (4)
H31D	−0.1762	0.5418	0.5535	0.032*
H31E	−0.0993	0.5927	0.5872	0.032*
H31F	−0.1061	0.3840	0.5747	0.032*
C4B	0.21489 (16)	0.5116 (3)	0.54475 (4)	0.0163 (4)
O4B	0.20078 (12)	0.5488 (2)	0.51144 (3)	0.0202 (3)
C42B	0.1625 (3)	0.7320 (3)	0.50383 (6)	0.0439 (7)
H42D	0.1712	0.7560	0.4801	0.066*
H42E	0.2134	0.8187	0.5171	0.066*
H42F	0.0765	0.7472	0.5090	0.066*
C5B	0.33243 (16)	0.4725 (3)	0.55861 (5)	0.0157 (4)
C6B	0.34987 (16)	0.4355 (3)	0.59241 (5)	0.0162 (4)
H6B	0.4297	0.4098	0.6018	0.019*
C1'B	0.36902 (16)	0.3374 (3)	0.70322 (4)	0.0151 (4)
C2'B	0.46956 (16)	0.2490 (3)	0.71888 (5)	0.0163 (4)
H2'B	0.5302	0.1969	0.7057	0.020*
C3'B	0.48306 (15)	0.2356 (3)	0.75291 (5)	0.0144 (4)
H3'B	0.5521	0.1732	0.7628	0.017*
C4'B	0.39701 (15)	0.3122 (2)	0.77304 (4)	0.0122 (4)
S4'B	0.42812 (4)	0.29019 (7)	0.81617 (2)	0.01773 (12)
C41B	0.2914 (2)	0.3764 (3)	0.83334 (5)	0.0317 (5)
H41D	0.2204	0.3074	0.8241	0.047*
H41E	0.2815	0.5068	0.8277	0.047*
H41F	0.2975	0.3621	0.8576	0.047*
C5'B	0.29495 (15)	0.4007 (3)	0.75807 (4)	0.0142 (4)
H5'B	0.2348	0.4532	0.7714	0.017*
C6'B	0.28167 (16)	0.4117 (3)	0.72358 (5)	0.0155 (4)
H6'B	0.2116	0.4712	0.7136	0.019*
C8B	0.36040 (16)	0.3535 (3)	0.66673 (5)	0.0167 (4)
H8B	0.4314	0.3243	0.6552	0.020*
C7B	0.26096 (17)	0.4057 (3)	0.64865 (5)	0.0167 (4)
H7B	0.1891	0.4256	0.6604	0.020*
O5B	0.42281 (11)	0.47856 (19)	0.53670 (3)	0.0190 (3)
C51B	0.54412 (16)	0.4313 (3)	0.54911 (5)	0.0219 (4)
H51D	0.5995	0.4318	0.5308	0.033*
H51E	0.5433	0.3085	0.5591	0.033*
H51F	0.5725	0.5211	0.5659	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0192 (9)	0.0128 (9)	0.0130 (9)	0.0021 (7)	−0.0003 (7)	−0.0014 (7)
C2A	0.0155 (9)	0.0145 (9)	0.0165 (9)	0.0028 (7)	−0.0018 (7)	−0.0012 (8)
C3A	0.0171 (9)	0.0138 (9)	0.0170 (9)	0.0025 (7)	0.0029 (7)	−0.0008 (8)
O3A	0.0140 (6)	0.0296 (8)	0.0221 (7)	0.0015 (6)	0.0039 (5)	0.0036 (6)
C31A	0.0155 (9)	0.0284 (12)	0.0323 (12)	0.0007 (8)	0.0030 (8)	0.0001 (10)
C4A	0.0196 (9)	0.0125 (9)	0.0107 (9)	0.0025 (7)	0.0006 (7)	0.0010 (7)
O4A	0.0220 (7)	0.0202 (7)	0.0101 (6)	0.0009 (6)	0.0015 (5)	0.0036 (5)
C42A	0.0349 (11)	0.0262 (11)	0.0111 (9)	0.0048 (9)	0.0006 (8)	−0.0021 (8)
C5A	0.0147 (8)	0.0141 (9)	0.0152 (9)	0.0005 (7)	−0.0004 (7)	−0.0014 (7)
O5A	0.0142 (6)	0.0304 (8)	0.0129 (6)	0.0005 (6)	0.0007 (5)	0.0018 (6)
C51A	0.0142 (9)	0.0259 (11)	0.0209 (10)	−0.0008 (8)	0.0021 (7)	−0.0018 (9)
C6A	0.0153 (9)	0.0168 (10)	0.0146 (9)	0.0002 (7)	0.0040 (7)	−0.0001 (8)
C7A	0.0151 (8)	0.0181 (10)	0.0131 (9)	0.0027 (7)	−0.0017 (7)	−0.0013 (8)
C8A	0.0164 (9)	0.0143 (9)	0.0163 (9)	0.0014 (7)	−0.0023 (7)	−0.0015 (8)
C1'A	0.0161 (8)	0.0123 (9)	0.0134 (9)	0.0039 (7)	0.0010 (7)	0.0002 (7)
C2'A	0.0153 (9)	0.0142 (9)	0.0175 (9)	−0.0009 (7)	−0.0017 (7)	0.0000 (8)
C3'A	0.0139 (8)	0.0162 (10)	0.0167 (9)	0.0005 (7)	0.0032 (7)	0.0039 (8)
C4'A	0.0157 (8)	0.0137 (9)	0.0112 (8)	0.0056 (7)	0.0016 (6)	0.0018 (7)
S4'A	0.0175 (2)	0.0333 (3)	0.0104 (2)	0.0057 (2)	0.00160 (17)	0.0031 (2)
C41A	0.0235 (10)	0.0237 (11)	0.0159 (10)	−0.0011 (8)	−0.0038 (7)	0.0012 (8)
C5'A	0.0120 (8)	0.0133 (9)	0.0151 (9)	0.0009 (7)	0.0002 (7)	0.0011 (7)
C6'A	0.0137 (8)	0.0139 (9)	0.0155 (9)	0.0020 (7)	0.0048 (7)	0.0017 (7)
C1B	0.0231 (9)	0.0119 (9)	0.0113 (9)	−0.0020 (7)	0.0008 (7)	0.0003 (7)
C2B	0.0197 (9)	0.0182 (10)	0.0133 (9)	−0.0021 (8)	0.0037 (7)	−0.0010 (8)
C3B	0.0177 (9)	0.0171 (10)	0.0146 (9)	0.0000 (8)	0.0006 (7)	0.0000 (8)
O3B	0.0164 (6)	0.0330 (9)	0.0162 (7)	−0.0001 (6)	0.0006 (5)	0.0040 (6)
C31B	0.0165 (9)	0.0252 (11)	0.0224 (10)	0.0010 (8)	0.0033 (7)	0.0003 (9)
C4B	0.0218 (9)	0.0178 (10)	0.0092 (9)	0.0004 (8)	0.0004 (7)	−0.0006 (7)
O4B	0.0233 (7)	0.0278 (8)	0.0093 (6)	0.0045 (6)	−0.0002 (5)	0.0019 (6)
C42B	0.090 (2)	0.0246 (13)	0.0172 (11)	0.0015 (13)	0.0062 (12)	0.0072 (10)
C5B	0.0183 (9)	0.0143 (9)	0.0148 (9)	0.0001 (7)	0.0033 (7)	−0.0013 (8)
C6B	0.0168 (9)	0.0147 (9)	0.0167 (9)	0.0019 (7)	−0.0021 (7)	0.0010 (8)
C1'B	0.0186 (9)	0.0131 (9)	0.0137 (9)	−0.0038 (7)	0.0008 (7)	0.0002 (7)
C2'B	0.0169 (9)	0.0141 (9)	0.0182 (9)	0.0003 (7)	0.0042 (7)	0.0001 (8)
C3'B	0.0123 (8)	0.0137 (9)	0.0172 (9)	0.0007 (7)	0.0002 (7)	0.0026 (8)
C4'B	0.0134 (8)	0.0111 (9)	0.0121 (9)	−0.0027 (7)	−0.0004 (6)	0.0006 (7)
S4'B	0.0197 (2)	0.0221 (3)	0.0111 (2)	−0.00184 (19)	−0.00153 (17)	0.00227 (19)
C41B	0.0428 (13)	0.0374 (14)	0.0159 (10)	0.0134 (11)	0.0110 (9)	0.0021 (10)
C5'B	0.0114 (8)	0.0136 (9)	0.0175 (9)	0.0000 (7)	0.0008 (7)	0.0006 (7)
C6'B	0.0127 (8)	0.0143 (9)	0.0187 (9)	−0.0001 (7)	−0.0056 (7)	0.0022 (8)
C8B	0.0183 (9)	0.0160 (9)	0.0163 (9)	0.0006 (7)	0.0038 (7)	0.0004 (8)
C7B	0.0199 (9)	0.0162 (9)	0.0143 (9)	−0.0003 (8)	0.0029 (7)	−0.0002 (8)
O5B	0.0172 (6)	0.0263 (8)	0.0138 (7)	0.0035 (6)	0.0030 (5)	0.0005 (6)
C51B	0.0175 (9)	0.0249 (11)	0.0233 (10)	0.0054 (8)	0.0024 (8)	0.0019 (9)

Geometric parameters (Å, º)

C1A—C2A	1.389 (3)	C1B—C2B	1.391 (3)
C1A—C6A	1.403 (2)	C1B—C6B	1.402 (3)
C1A—C7A	1.471 (2)	C1B—C7B	1.465 (2)
C2A—C3A	1.387 (2)	C2B—C3B	1.388 (3)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—O3A	1.367 (2)	C3B—O3B	1.365 (2)
C3A—C4A	1.397 (2)	C3B—C4B	1.398 (3)
O3A—C31A	1.424 (2)	O3B—C31B	1.424 (2)
C31A—H31A	0.9800	C31B—H31D	0.9800
C31A—H31B	0.9800	C31B—H31E	0.9800
C31A—H31C	0.9800	C31B—H31F	0.9800
C4A—O4A	1.367 (2)	C4B—O4B	1.369 (2)
C4A—C5A	1.397 (2)	C4B—C5B	1.402 (2)
O4A—C42A	1.440 (2)	O4B—C42B	1.425 (3)
C42A—H42A	0.9800	C42B—H42D	0.9800
C42A—H42B	0.9800	C42B—H42E	0.9800
C42A—H42C	0.9800	C42B—H42F	0.9800
C5A—O5A	1.367 (2)	C5B—O5B	1.360 (2)
C5A—C6A	1.389 (2)	C5B—C6B	1.391 (3)
O5A—C51A	1.426 (2)	C6B—H6B	0.9500
C51A—H51A	0.9800	C1'B—C2'B	1.394 (2)
C51A—H51B	0.9800	C1'B—C6'B	1.400 (3)
C51A—H51C	0.9800	C1'B—C8B	1.473 (3)
C6A—H6A	0.9500	C2'B—C3'B	1.374 (2)
C7A—C8A	1.331 (3)	C2'B—H2'B	0.9500
C7A—H7A	0.9500	C3'B—C4'B	1.391 (2)
C8A—C1'A	1.466 (2)	C3'B—H3'B	0.9500
C8A—H8A	0.9500	C4'B—C5'B	1.396 (2)
C1'A—C6'A	1.400 (2)	C4'B—S4'B	1.7594 (17)
C1'A—C2'A	1.400 (3)	S4'B—C41B	1.794 (2)
C2'A—C3'A	1.374 (2)	C41B—H41D	0.9800
C2'A—H2'A	0.9500	C41B—H41E	0.9800
C3'A—C4'A	1.392 (2)	C41B—H41F	0.9800
C3'A—H3'A	0.9500	C5'B—C6'B	1.391 (2)
C4'A—C5'A	1.398 (2)	C5'B—H5'B	0.9500
C4'A—S4'A	1.7581 (18)	C6'B—H6'B	0.9500
S4'A—C41A	1.7998 (19)	C8B—C7B	1.330 (3)
C41A—H41A	0.9800	C8B—H8B	0.9500
C41A—H41B	0.9800	C7B—H7B	0.9500
C41A—H41C	0.9800	O5B—C51B	1.433 (2)
C5'A—C6'A	1.388 (2)	C51B—H51D	0.9800
C5'A—H5'A	0.9500	C51B—H51E	0.9800
C6'A—H6'A	0.9500	C51B—H51F	0.9800
C2A—C1A—C6A	119.82 (16)	C2B—C1B—C6B	119.78 (16)
C2A—C1A—C7A	118.08 (15)	C2B—C1B—C7B	116.95 (16)
C6A—C1A—C7A	121.94 (16)	C6B—C1B—C7B	123.25 (16)
C3A—C2A—C1A	120.35 (16)	C3B—C2B—C1B	120.31 (17)
C3A—C2A—H2A	119.8	C3B—C2B—H2B	119.8
C1A—C2A—H2A	119.8	C1B—C2B—H2B	119.8
O3A—C3A—C2A	124.52 (16)	O3B—C3B—C2B	124.14 (16)
O3A—C3A—C4A	115.06 (16)	O3B—C3B—C4B	115.53 (16)
C2A—C3A—C4A	120.40 (17)	C2B—C3B—C4B	120.32 (16)
C3A—O3A—C31A	117.98 (15)	C3B—O3B—C31B	117.75 (15)
O3A—C31A—H31A	109.5	O3B—C31B—H31D	109.5
O3A—C31A—H31B	109.5	O3B—C31B—H31E	109.5
H31A—C31A—H31B	109.5	H31D—C31B—H31E	109.5
O3A—C31A—H31C	109.5	O3B—C31B—H31F	109.5
H31A—C31A—H31C	109.5	H31D—C31B—H31F	109.5
H31B—C31A—H31C	109.5	H31E—C31B—H31F	109.5
O4A—C4A—C3A	119.93 (16)	O4B—C4B—C3B	121.77 (16)
O4A—C4A—C5A	120.70 (15)	O4B—C4B—C5B	118.86 (16)
C3A—C4A—C5A	119.11 (16)	C3B—C4B—C5B	119.35 (17)
C4A—O4A—C42A	114.27 (15)	C4B—O4B—C42B	114.31 (16)
O4A—C42A—H42A	109.5	O4B—C42B—H42D	109.5
O4A—C42A—H42B	109.5	O4B—C42B—H42E	109.5
H42A—C42A—H42B	109.5	H42D—C42B—H42E	109.5
O4A—C42A—H42C	109.5	O4B—C42B—H42F	109.5
H42A—C42A—H42C	109.5	H42D—C42B—H42F	109.5
H42B—C42A—H42C	109.5	H42E—C42B—H42F	109.5
O5A—C5A—C6A	124.71 (16)	O5B—C5B—C6B	125.13 (16)
O5A—C5A—C4A	114.48 (16)	O5B—C5B—C4B	114.63 (16)
C6A—C5A—C4A	120.77 (16)	C6B—C5B—C4B	120.22 (17)
C5A—O5A—C51A	117.21 (14)	C5B—C6B—C1B	119.95 (16)
O5A—C51A—H51A	109.5	C5B—C6B—H6B	120.0
O5A—C51A—H51B	109.5	C1B—C6B—H6B	120.0
H51A—C51A—H51B	109.5	C2'B—C1'B—C6'B	117.29 (16)
O5A—C51A—H51C	109.5	C2'B—C1'B—C8B	119.65 (16)
H51A—C51A—H51C	109.5	C6'B—C1'B—C8B	123.03 (16)
H51B—C51A—H51C	109.5	C3'B—C2'B—C1'B	121.58 (17)
C5A—C6A—C1A	119.53 (16)	C3'B—C2'B—H2'B	119.2
C5A—C6A—H6A	120.2	C1'B—C2'B—H2'B	119.2
C1A—C6A—H6A	120.2	C2'B—C3'B—C4'B	120.90 (16)
C8A—C7A—C1A	126.91 (16)	C2'B—C3'B—H3'B	119.5
C8A—C7A—H7A	116.5	C4'B—C3'B—H3'B	119.5
C1A—C7A—H7A	116.5	C3'B—C4'B—C5'B	118.83 (16)
C7A—C8A—C1'A	126.40 (16)	C3'B—C4'B—S4'B	116.01 (13)
C7A—C8A—H8A	116.8	C5'B—C4'B—S4'B	125.15 (14)
C1'A—C8A—H8A	116.8	C4'B—S4'B—C41B	103.20 (9)
C6'A—C1'A—C2'A	117.22 (16)	S4'B—C41B—H41D	109.5
C6'A—C1'A—C8A	123.06 (16)	S4'B—C41B—H41E	109.5
C2'A—C1'A—C8A	119.66 (16)	H41D—C41B—H41E	109.5
C3'A—C2'A—C1'A	121.78 (16)	S4'B—C41B—H41F	109.5
C3'A—C2'A—H2'A	119.1	H41D—C41B—H41F	109.5
C1'A—C2'A—H2'A	119.1	H41E—C41B—H41F	109.5
C2'A—C3'A—C4'A	120.64 (16)	C6'B—C5'B—C4'B	119.71 (17)
C2'A—C3'A—H3'A	119.7	C6'B—C5'B—H5'B	120.1
C4'A—C3'A—H3'A	119.7	C4'B—C5'B—H5'B	120.1
C3'A—C4'A—C5'A	118.73 (16)	C5'B—C6'B—C1'B	121.67 (16)
C3'A—C4'A—S4'A	117.31 (14)	C5'B—C6'B—H6'B	119.2
C5'A—C4'A—S4'A	123.91 (14)	C1'B—C6'B—H6'B	119.2
C4'A—S4'A—C41A	103.71 (9)	C7B—C8B—C1'B	125.13 (17)
S4'A—C41A—H41A	109.5	C7B—C8B—H8B	117.4
S4'A—C41A—H41B	109.5	C1'B—C8B—H8B	117.4
H41A—C41A—H41B	109.5	C8B—C7B—C1B	127.45 (17)
S4'A—C41A—H41C	109.5	C8B—C7B—H7B	116.3
H41A—C41A—H41C	109.5	C1B—C7B—H7B	116.3
H41B—C41A—H41C	109.5	C5B—O5B—C51B	117.14 (14)
C6'A—C5'A—C4'A	120.19 (16)	O5B—C51B—H51D	109.5
C6'A—C5'A—H5'A	119.9	O5B—C51B—H51E	109.5
C4'A—C5'A—H5'A	119.9	H51D—C51B—H51E	109.5
C5'A—C6'A—C1'A	121.43 (16)	O5B—C51B—H51F	109.5
C5'A—C6'A—H6'A	119.3	H51D—C51B—H51F	109.5
C1'A—C6'A—H6'A	119.3	H51E—C51B—H51F	109.5
C6A—C1A—C2A—C3A	−0.7 (3)	C6B—C1B—C2B—C3B	−0.5 (3)
C7A—C1A—C2A—C3A	174.92 (17)	C7B—C1B—C2B—C3B	178.16 (17)
C1A—C2A—C3A—O3A	−177.86 (18)	C1B—C2B—C3B—O3B	179.71 (18)
C1A—C2A—C3A—C4A	0.3 (3)	C1B—C2B—C3B—C4B	−1.5 (3)
C2A—C3A—O3A—C31A	4.5 (3)	C2B—C3B—O3B—C31B	−9.7 (3)
C4A—C3A—O3A—C31A	−173.74 (17)	C4B—C3B—O3B—C31B	171.52 (17)
O3A—C3A—C4A—O4A	4.0 (3)	O3B—C3B—C4B—O4B	−0.2 (3)
C2A—C3A—C4A—O4A	−174.35 (17)	C2B—C3B—C4B—O4B	−179.02 (17)
O3A—C3A—C4A—C5A	178.16 (16)	O3B—C3B—C4B—C5B	−178.24 (17)
C2A—C3A—C4A—C5A	−0.2 (3)	C2B—C3B—C4B—C5B	2.9 (3)
C3A—C4A—O4A—C42A	−101.9 (2)	C3B—C4B—O4B—C42B	67.6 (3)
C5A—C4A—O4A—C42A	84.0 (2)	C5B—C4B—O4B—C42B	−114.3 (2)
O4A—C4A—C5A—O5A	−3.3 (3)	O4B—C4B—C5B—O5B	0.9 (3)
C3A—C4A—C5A—O5A	−177.49 (16)	C3B—C4B—C5B—O5B	179.00 (17)
O4A—C4A—C5A—C6A	174.56 (17)	O4B—C4B—C5B—C6B	179.54 (17)
C3A—C4A—C5A—C6A	0.4 (3)	C3B—C4B—C5B—C6B	−2.3 (3)
C6A—C5A—O5A—C51A	−4.1 (3)	O5B—C5B—C6B—C1B	178.92 (18)
C4A—C5A—O5A—C51A	173.72 (16)	C4B—C5B—C6B—C1B	0.4 (3)
O5A—C5A—C6A—C1A	176.88 (17)	C2B—C1B—C6B—C5B	1.0 (3)
C4A—C5A—C6A—C1A	−0.8 (3)	C7B—C1B—C6B—C5B	−177.50 (18)
C2A—C1A—C6A—C5A	0.9 (3)	C6'B—C1'B—C2'B—C3'B	−0.2 (3)
C7A—C1A—C6A—C5A	−174.49 (17)	C8B—C1'B—C2'B—C3'B	178.07 (17)
C2A—C1A—C7A—C8A	172.15 (19)	C1'B—C2'B—C3'B—C4'B	−0.8 (3)
C6A—C1A—C7A—C8A	−12.4 (3)	C2'B—C3'B—C4'B—C5'B	1.1 (3)
C1A—C7A—C8A—C1'A	173.35 (18)	C2'B—C3'B—C4'B—S4'B	−178.29 (14)
C7A—C8A—C1'A—C6'A	−11.4 (3)	C3'B—C4'B—S4'B—C41B	−172.99 (15)
C7A—C8A—C1'A—C2'A	171.54 (19)	C5'B—C4'B—S4'B—C41B	7.66 (19)
C6'A—C1'A—C2'A—C3'A	−0.2 (3)	C3'B—C4'B—C5'B—C6'B	−0.4 (3)
C8A—C1'A—C2'A—C3'A	177.03 (17)	S4'B—C4'B—C5'B—C6'B	178.91 (14)
C1'A—C2'A—C3'A—C4'A	−0.4 (3)	C4'B—C5'B—C6'B—C1'B	−0.6 (3)
C2'A—C3'A—C4'A—C5'A	0.9 (3)	C2'B—C1'B—C6'B—C5'B	0.9 (3)
C2'A—C3'A—C4'A—S4'A	−176.50 (14)	C8B—C1'B—C6'B—C5'B	−177.33 (17)
C3'A—C4'A—S4'A—C41A	−160.45 (15)	C2'B—C1'B—C8B—C7B	167.97 (19)
C5'A—C4'A—S4'A—C41A	22.33 (18)	C6'B—C1'B—C8B—C7B	−13.8 (3)
C3'A—C4'A—C5'A—C6'A	−0.7 (3)	C1'B—C8B—C7B—C1B	175.50 (18)
S4'A—C4'A—C5'A—C6'A	176.46 (14)	C2B—C1B—C7B—C8B	173.1 (2)
C4'A—C5'A—C6'A—C1'A	0.1 (3)	C6B—C1B—C7B—C8B	−8.3 (3)
C2'A—C1'A—C6'A—C5'A	0.4 (3)	C6B—C5B—O5B—C51B	4.3 (3)
C8A—C1'A—C6'A—C5'A	−176.78 (17)	C4B—C5B—O5B—C51B	−177.12 (17)

1-[(E)-2-(2,4,6-Trimethoxyphenyl)ethenyl]-4-(methylsulfanyl)benzene (9)

Crystal data

C18H20O3S	F(000) = 672
Mr = 316.40	Dx = 1.288 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.2520 (5) Å	Cell parameters from 2950 reflections
b = 7.05630 (19) Å	θ = 3.6–26.9°
c = 19.1866 (6) Å	µ = 0.21 mm^−1
β = 100.261 (3)°	T = 295 K
V = 1632.22 (10) Å^3	Plate, colourless
Z = 4	0.25 × 0.2 × 0.07 mm

Data collection

Rigaku OD Xcalibur Eos diffractometer	2882 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2177 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 16.2413 pixels mm^-1	θmax = 25.0°, θmin = 3.4°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	k = −8→8
Tmin = 0.914, Tmax = 1.000	l = −21→22
10241 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0454P)^2 + 0.2779P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2882 reflections	Δρmax = 0.14 e Å^−3
203 parameters	Δρmin = −0.24 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.23065 (13)	0.1850 (2)	0.51421 (8)	0.0417 (4)
C2	0.23653 (14)	0.1917 (2)	0.58854 (9)	0.0446 (4)
O2	0.28784 (11)	0.34820 (18)	0.62131 (6)	0.0598 (4)
C21	0.2972 (2)	0.3625 (3)	0.69622 (10)	0.0779 (7)
H21A	0.2245	0.3636	0.7084	0.117*
H21B	0.3353	0.4776	0.7124	0.117*
H21C	0.3382	0.2560	0.7184	0.117*
C3	0.19273 (15)	0.0509 (2)	0.62466 (9)	0.0492 (4)
H3	0.1974	0.0595	0.6735	0.059*
C4	0.14191 (15)	−0.1031 (2)	0.58831 (9)	0.0479 (4)
O4	0.10242 (12)	−0.23555 (19)	0.62965 (7)	0.0670 (4)
C41	0.04206 (18)	−0.3921 (3)	0.59593 (11)	0.0697 (6)
H41A	−0.0211	−0.3469	0.5632	0.105*
H41B	0.0176	−0.4708	0.6310	0.105*
H41C	0.0889	−0.4645	0.5708	0.105*
C5	0.13342 (14)	−0.1175 (2)	0.51591 (9)	0.0474 (4)
H5	0.0993	−0.2219	0.4917	0.057*
C6	0.17675 (14)	0.0270 (2)	0.47974 (8)	0.0425 (4)
O6	0.16836 (11)	0.02479 (17)	0.40791 (6)	0.0566 (4)
C61	0.11255 (17)	−0.1292 (3)	0.36915 (9)	0.0599 (5)
H61A	0.1125	−0.1113	0.3195	0.090*
H61B	0.0375	−0.1349	0.3772	0.090*
H61C	0.1500	−0.2454	0.3845	0.090*
C7	0.27976 (14)	0.3415 (2)	0.48018 (9)	0.0467 (4)
H7	0.3086	0.4380	0.5110	0.056*
C8	0.29068 (14)	0.3708 (2)	0.41367 (9)	0.0490 (4)
H8	0.2633	0.2782	0.3807	0.059*
C1'	0.34262 (14)	0.5379 (2)	0.38774 (9)	0.0448 (4)
C2'	0.33926 (16)	0.5644 (3)	0.31597 (9)	0.0535 (5)
H2'	0.3051	0.4734	0.2844	0.064*
C3'	0.38501 (16)	0.7218 (3)	0.28997 (10)	0.0572 (5)
H3'	0.3814	0.7347	0.2414	0.069*
C4'	0.43628 (15)	0.8611 (2)	0.33493 (9)	0.0514 (5)
S4'	0.48868 (6)	1.06088 (8)	0.29681 (3)	0.0804 (2)
C41'	0.55207 (18)	1.1967 (3)	0.37127 (12)	0.0763 (6)
H41D	0.5812	1.3119	0.3553	0.114*
H41E	0.6113	1.1250	0.3986	0.114*
H41F	0.4979	1.2265	0.4001	0.114*
C5'	0.44241 (19)	0.8341 (3)	0.40672 (10)	0.0714 (6)
H5'	0.4777	0.9240	0.4384	0.086*
C6'	0.39687 (18)	0.6754 (3)	0.43199 (10)	0.0673 (6)
H6'	0.4029	0.6604	0.4807	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0443 (9)	0.0454 (9)	0.0367 (9)	0.0044 (8)	0.0105 (7)	0.0003 (8)
C2	0.0492 (10)	0.0486 (10)	0.0364 (9)	0.0026 (8)	0.0085 (8)	−0.0023 (8)
O2	0.0839 (9)	0.0616 (8)	0.0351 (7)	−0.0171 (7)	0.0140 (6)	−0.0088 (6)
C21	0.1135 (19)	0.0835 (15)	0.0390 (11)	−0.0281 (14)	0.0198 (11)	−0.0157 (11)
C3	0.0580 (11)	0.0586 (11)	0.0321 (9)	0.0001 (9)	0.0111 (8)	0.0022 (8)
C4	0.0511 (11)	0.0500 (10)	0.0441 (10)	0.0030 (9)	0.0124 (8)	0.0078 (8)
O4	0.0890 (10)	0.0642 (8)	0.0492 (8)	−0.0180 (8)	0.0159 (7)	0.0089 (7)
C41	0.0799 (15)	0.0581 (12)	0.0714 (14)	−0.0135 (11)	0.0141 (12)	0.0096 (11)
C5	0.0527 (11)	0.0455 (9)	0.0438 (10)	0.0003 (8)	0.0082 (8)	−0.0010 (8)
C6	0.0452 (10)	0.0478 (10)	0.0350 (9)	0.0062 (8)	0.0085 (7)	−0.0018 (8)
O6	0.0787 (9)	0.0579 (8)	0.0338 (7)	−0.0118 (7)	0.0121 (6)	−0.0065 (6)
C61	0.0761 (14)	0.0605 (11)	0.0430 (10)	−0.0080 (11)	0.0104 (10)	−0.0127 (9)
C7	0.0541 (11)	0.0489 (10)	0.0378 (10)	−0.0010 (9)	0.0100 (8)	−0.0031 (8)
C8	0.0564 (11)	0.0526 (10)	0.0377 (10)	−0.0049 (9)	0.0079 (8)	−0.0041 (8)
C1'	0.0472 (10)	0.0499 (10)	0.0373 (9)	0.0018 (8)	0.0076 (8)	0.0003 (8)
C2'	0.0675 (12)	0.0547 (11)	0.0383 (10)	−0.0071 (10)	0.0093 (9)	−0.0043 (8)
C3'	0.0752 (13)	0.0606 (12)	0.0367 (10)	−0.0010 (10)	0.0120 (9)	0.0049 (9)
C4'	0.0586 (11)	0.0498 (10)	0.0459 (10)	0.0011 (9)	0.0101 (9)	0.0053 (9)
S4'	0.1132 (5)	0.0633 (4)	0.0657 (4)	−0.0185 (3)	0.0188 (3)	0.0140 (3)
C41'	0.0771 (15)	0.0553 (12)	0.0973 (17)	−0.0077 (11)	0.0178 (13)	−0.0019 (12)
C5'	0.0980 (17)	0.0680 (13)	0.0458 (11)	−0.0276 (12)	0.0064 (11)	−0.0062 (10)
C6'	0.0931 (16)	0.0741 (13)	0.0340 (10)	−0.0223 (12)	0.0094 (10)	0.0018 (10)

Geometric parameters (Å, º)

C1—C6	1.400 (2)	C61—H61B	0.9600
C1—C2	1.416 (2)	C61—H61C	0.9600
C1—C7	1.465 (2)	C7—C8	1.323 (2)
C2—O2	1.3670 (19)	C7—H7	0.9300
C2—C3	1.374 (2)	C8—C1'	1.468 (2)
O2—C21	1.425 (2)	C8—H8	0.9300
C21—H21A	0.9600	C1'—C6'	1.379 (2)
C21—H21B	0.9600	C1'—C2'	1.383 (2)
C21—H21C	0.9600	C2'—C3'	1.377 (2)
C3—C4	1.379 (2)	C2'—H2'	0.9300
C3—H3	0.9300	C3'—C4'	1.383 (2)
C4—O4	1.369 (2)	C3'—H3'	0.9300
C4—C5	1.378 (2)	C4'—C5'	1.379 (3)
O4—C41	1.420 (2)	C4'—S4'	1.7611 (18)
C41—H41A	0.9600	S4'—C41'	1.780 (2)
C41—H41B	0.9600	C41'—H41D	0.9600
C41—H41C	0.9600	C41'—H41E	0.9600
C5—C6	1.391 (2)	C41'—H41F	0.9600
C5—H5	0.9300	C5'—C6'	1.377 (3)
C6—O6	1.3636 (19)	C5'—H5'	0.9300
O6—C61	1.421 (2)	C6'—H6'	0.9300
C61—H61A	0.9600
C6—C1—C2	115.95 (15)	H61A—C61—H61B	109.5
C6—C1—C7	125.87 (15)	O6—C61—H61C	109.5
C2—C1—C7	118.17 (15)	H61A—C61—H61C	109.5
O2—C2—C3	122.74 (15)	H61B—C61—H61C	109.5
O2—C2—C1	115.30 (14)	C8—C7—C1	131.90 (17)
C3—C2—C1	121.96 (16)	C8—C7—H7	114.0
C2—O2—C21	117.98 (14)	C1—C7—H7	114.0
O2—C21—H21A	109.5	C7—C8—C1'	125.25 (16)
O2—C21—H21B	109.5	C7—C8—H8	117.4
H21A—C21—H21B	109.5	C1'—C8—H8	117.4
O2—C21—H21C	109.5	C6'—C1'—C2'	116.31 (16)
H21A—C21—H21C	109.5	C6'—C1'—C8	123.14 (15)
H21B—C21—H21C	109.5	C2'—C1'—C8	120.55 (16)
C2—C3—C4	119.78 (15)	C3'—C2'—C1'	121.87 (17)
C2—C3—H3	120.1	C3'—C2'—H2'	119.1
C4—C3—H3	120.1	C1'—C2'—H2'	119.1
O4—C4—C5	124.27 (17)	C2'—C3'—C4'	121.09 (17)
O4—C4—C3	114.80 (15)	C2'—C3'—H3'	119.5
C5—C4—C3	120.93 (16)	C4'—C3'—H3'	119.5
C4—O4—C41	118.45 (14)	C5'—C4'—C3'	117.56 (17)
O4—C41—H41A	109.5	C5'—C4'—S4'	124.49 (15)
O4—C41—H41B	109.5	C3'—C4'—S4'	117.95 (13)
H41A—C41—H41B	109.5	C4'—S4'—C41'	103.71 (10)
O4—C41—H41C	109.5	S4'—C41'—H41D	109.5
H41A—C41—H41C	109.5	S4'—C41'—H41E	109.5
H41B—C41—H41C	109.5	H41D—C41'—H41E	109.5
C4—C5—C6	118.83 (16)	S4'—C41'—H41F	109.5
C4—C5—H5	120.6	H41D—C41'—H41F	109.5
C6—C5—H5	120.6	H41E—C41'—H41F	109.5
O6—C6—C5	121.96 (15)	C6'—C5'—C4'	120.70 (18)
O6—C6—C1	115.50 (14)	C6'—C5'—H5'	119.6
C5—C6—C1	122.53 (15)	C4'—C5'—H5'	119.6
C6—O6—C61	118.69 (14)	C5'—C6'—C1'	122.43 (17)
O6—C61—H61A	109.5	C5'—C6'—H6'	118.8
O6—C61—H61B	109.5	C1'—C6'—H6'	118.8

Comparison of the relevant geometrical paraeters found in the crystal structures of 4 and 7 and in the appropriate molecules docked at the active sites (cf. text)

	4	4_1A2	4_1B1	7	7_1A2	7_1B1
C1—C7	1.4673 (18)	1.455	1.468	1.476 (7)	1.462	1.468
C7—C8	1.339 (2)	1.348	1.352	1.335 (6)	1.344	1.345
C8—C1'	1.4659 (19)	1.457	1.474	1.467 (6)	1.451	1.467
C4'—S4'	1.7623 (14)	1.753	1.777	1.765 (5)	1.748	1.765
S4'—C41'	1.7996 (16)	1.800	1.801	1.792 (5)	1.802	1.796
C3'—C4'-C5'	119.43 (12)	120.81	119.77	119.4 (5)	121.02	120.04
C4'—S4'—C41'	103.29 (7)	95.36	98.73	103.7 (3)	94.16	96.79
C1—C7—C8—C1'	174.48 (13)	-177.24	178.47	-175.94	172.98	-169.52
C7═C8···S4'—C41'	-15.1	-80.33	-136.76	166.0	-33.59	-36.46
A/B	27.30 (11)	36.60	26.15	11.8 (9)	23.45	30.33
B/A'	10.0 (2)	18.42	39.35	6.7 (9)	30.17	31.49
A/A'	37.13 (5)	18.54	13.60	6.1 (3)	13.16	8.28
A/OMe	19.01 (14) 2.1 (2)	27.06 13.59	18.75 2.40	4.2 (5) 13.0 (6) 4.9 (4)	7.00 19.95 42.71	2.98 84.85 51.30
A'/SMe	7.87 (10)	61.13	71.08	19.0 (4)	65.74	61.44

Percentage shares of different intermolecular contacts to the Hirshfeld surface

	1	2	3	4	5A	5B	6A	6B	7	8	9
C···C	0.1	0.2	0.1	1.1	0.4	0.4	0.1	0.1	0	0	0.5
C···O	0.2	0	0.3	0.6	0.4	0.4	0.1	0.1	0.1	0.4	2.3
C···H	36.4	36.2	32.2	31.1	32.4	33.0	31.1	27.6	31.0	32.7	27.6
C···S	0.9	0	0.7	0	0.1	0.1	0.2	0.1	0.1	0	0.0
O···O	0	0	0.1	0	0.4	0.4	0.2	0.7	0	0	0.2
O···H	4.1	6.3	7.1	8.8	10.2	9.6	10.8	14.1	13.9	9.5	9.5
O···S	0.3	0	0	0	0	0.1	0	0	0.7	0.2	0.0
H···H	48.1	48.0	51.2	49.0	47.3	47.1	49.0	49.4	46.0	47.8	52.2
H···S	9.8	9.2	8.2	9.4	8.2	8.4	8.1	7.6	8.1	9.3	7.8
S···S	0	0	0.3	0	0.4	0.4	0.4	0.4	0	0	0

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