Crystal structure of 2-isopropyl-4-meth­oxy-5-methyl­phenyl 4-methyl­benzene­sulfonate

The title compound, an hemisynthetic product, was obtained by the tosyl­ation reaction of the naturally occurring meroterpene p-meth­oxy­thymol 1.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.110
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full           ! Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3'      ..O1               2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5'3     ..O3               2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A      ..O4               2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B     ..O3               2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A     ..O4               2.70 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          7 Note

Alert level G
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             120.7 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

2-Isopropyl-4-methoxy-5-methylphenyl 4-methylbenzenesulfonate

Crystal data

C18H22O4S	F(000) = 712
Mr = 334.41	Dx = 1.282 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2226 (6) Å	Cell parameters from 4433 reflections
b = 14.5382 (9) Å	θ = 3.8–28.5°
c = 14.7230 (8) Å	µ = 0.20 mm^−1
β = 100.020 (6)°	T = 173 K
V = 1733.17 (19) Å^3	Box, colourless
Z = 4	0.35 × 0.25 × 0.10 mm

Data collection

Rigaku Oxford Diffraction Xcalibur Eos Gemini ultra diffractometer	3532 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2777 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 16.1978 pixels mm^-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −18→16
Tmin = 0.791, Tmax = 1.000	l = −18→18
18172 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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 0.814P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3532 reflections	Δρmax = 0.34 e Å^−3
213 parameters	Δρmin = −0.34 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. All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.95 Å (aromatic), 0.98 Å (methyl), 1.0Å (methine) with U_iso(H) = 1.2U_eq(CH and C=CH) or U_iso(H) = 1.5U_eq(CH₃).

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

	x	y	z	Uiso*/Ueq
C1	0.0729 (2)	0.19454 (12)	0.12387 (12)	0.0244 (4)
C1'	0.2295 (2)	0.11565 (13)	0.32646 (12)	0.0273 (4)
C2'	0.2423 (2)	0.02563 (13)	0.29895 (13)	0.0319 (4)
H2'	0.150817	−0.004394	0.262620	0.038*
C2	0.2184 (2)	0.20290 (12)	0.08959 (12)	0.0253 (4)
C3'	0.3907 (3)	−0.02031 (14)	0.32514 (13)	0.0351 (5)
H3'	0.400221	−0.082269	0.306238	0.042*
C3	0.2171 (2)	0.16786 (13)	0.00089 (12)	0.0281 (4)
H3	0.314049	0.172671	−0.025740	0.034*
C4	0.0786 (2)	0.12650 (13)	−0.04881 (12)	0.0283 (4)
C4'	0.5259 (2)	0.02225 (14)	0.37844 (12)	0.0323 (4)
C5	−0.0681 (2)	0.11891 (13)	−0.01288 (13)	0.0293 (4)
C5'	0.6862 (3)	−0.02793 (16)	0.40828 (15)	0.0414 (5)
H5'1	0.674385	−0.091812	0.386905	0.062*
H5'2	0.714962	−0.026864	0.475724	0.062*
H5'3	0.773618	0.002185	0.381667	0.062*
C6	−0.0682 (2)	0.15452 (13)	0.07405 (13)	0.0284 (4)
H6	−0.166024	0.151593	0.100070	0.034*
C6'	0.5098 (2)	0.11365 (15)	0.40381 (13)	0.0356 (5)
H6'	0.601735	0.144317	0.439007	0.043*
C7	0.4269 (3)	0.32911 (16)	0.09104 (15)	0.0451 (6)
H7A	0.459446	0.308452	0.033416	0.068*
H7B	0.520807	0.359505	0.129571	0.068*
H7C	0.334786	0.372516	0.077095	0.068*
C7'	0.3633 (2)	0.16037 (14)	0.37888 (13)	0.0325 (4)
H7'	0.353664	0.222483	0.397271	0.039*
C8	0.3736 (2)	0.24634 (14)	0.14252 (13)	0.0310 (4)
H8	0.349050	0.268405	0.203020	0.037*
C9	0.5123 (3)	0.17540 (18)	0.16200 (16)	0.0483 (6)
H9A	0.474804	0.122497	0.194085	0.072*
H9B	0.608770	0.203173	0.200759	0.072*
H9C	0.542309	0.155001	0.103658	0.072*
C10	0.2226 (3)	0.08648 (18)	−0.17038 (15)	0.0526 (7)
H10A	0.261778	0.149089	−0.178548	0.079*
H10B	0.203927	0.054579	−0.229920	0.079*
H10C	0.305633	0.053107	−0.126849	0.079*
C11	−0.2193 (3)	0.07531 (15)	−0.06830 (14)	0.0388 (5)
H11A	−0.307373	0.073020	−0.031237	0.058*
H11B	−0.192880	0.012726	−0.085726	0.058*
H11C	−0.256290	0.111763	−0.124059	0.058*
O1	0.06333 (15)	0.23611 (8)	0.21065 (8)	0.0269 (3)
O2	0.07192 (18)	0.09037 (10)	−0.13523 (9)	0.0391 (4)
O3	−0.08697 (16)	0.10974 (10)	0.27106 (10)	0.0378 (3)
O4	0.02806 (17)	0.24132 (10)	0.36634 (9)	0.0386 (4)
S1	0.04212 (6)	0.17449 (3)	0.29760 (3)	0.02896 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0260 (9)	0.0203 (9)	0.0269 (9)	0.0030 (7)	0.0041 (7)	0.0025 (7)
C1'	0.0316 (9)	0.0231 (10)	0.0270 (9)	0.0023 (8)	0.0049 (7)	0.0001 (7)
C2'	0.0354 (10)	0.0247 (10)	0.0349 (10)	−0.0030 (8)	0.0038 (8)	−0.0036 (8)
C2	0.0248 (9)	0.0208 (9)	0.0298 (9)	−0.0004 (7)	0.0029 (7)	0.0022 (7)
C3'	0.0445 (12)	0.0226 (10)	0.0392 (11)	0.0032 (9)	0.0098 (9)	−0.0032 (8)
C3	0.0297 (9)	0.0242 (10)	0.0313 (9)	−0.0007 (8)	0.0084 (7)	0.0022 (8)
C4	0.0363 (10)	0.0210 (10)	0.0262 (9)	0.0000 (8)	0.0016 (7)	0.0025 (7)
C4'	0.0379 (11)	0.0306 (11)	0.0287 (9)	0.0052 (9)	0.0067 (8)	0.0033 (8)
C5	0.0301 (9)	0.0206 (10)	0.0349 (10)	−0.0003 (8)	−0.0013 (8)	0.0063 (8)
C5'	0.0415 (12)	0.0441 (13)	0.0398 (11)	0.0126 (10)	0.0103 (9)	0.0081 (10)
C6	0.0230 (9)	0.0255 (10)	0.0366 (10)	0.0030 (8)	0.0045 (7)	0.0067 (8)
C6'	0.0355 (11)	0.0355 (12)	0.0331 (10)	0.0002 (9)	−0.0019 (8)	−0.0039 (9)
C7	0.0464 (13)	0.0481 (14)	0.0418 (12)	−0.0235 (11)	0.0107 (10)	−0.0079 (10)
C7'	0.0395 (11)	0.0236 (10)	0.0327 (10)	0.0021 (8)	0.0017 (8)	−0.0047 (8)
C8	0.0251 (9)	0.0385 (12)	0.0297 (9)	−0.0050 (8)	0.0057 (7)	−0.0050 (8)
C9	0.0276 (10)	0.0672 (17)	0.0477 (13)	0.0069 (11)	0.0003 (9)	−0.0045 (12)
C10	0.0641 (16)	0.0617 (16)	0.0368 (12)	−0.0238 (13)	0.0219 (11)	−0.0168 (11)
C11	0.0359 (11)	0.0347 (12)	0.0416 (11)	−0.0050 (9)	−0.0046 (9)	0.0020 (9)
O1	0.0272 (6)	0.0225 (7)	0.0322 (7)	0.0011 (5)	0.0083 (5)	0.0012 (5)
O2	0.0473 (9)	0.0394 (9)	0.0305 (7)	−0.0112 (7)	0.0062 (6)	−0.0057 (6)
O3	0.0309 (7)	0.0380 (8)	0.0450 (8)	−0.0052 (6)	0.0079 (6)	0.0068 (6)
O4	0.0411 (8)	0.0403 (8)	0.0376 (8)	0.0094 (7)	0.0153 (6)	−0.0038 (6)
S1	0.0277 (2)	0.0285 (3)	0.0323 (3)	0.0020 (2)	0.00963 (18)	0.00179 (19)

Geometric parameters (Å, º)

C1—C2	1.382 (2)	C6—H6	0.9500
C1—C6	1.388 (2)	C6'—C7'	1.376 (3)
C1—O1	1.428 (2)	C6'—H6'	0.9500
C1'—C2'	1.379 (3)	C7—C8	1.526 (3)
C1'—C7'	1.390 (3)	C7—H7A	0.9800
C1'—S1	1.7486 (19)	C7—H7B	0.9800
C2'—C3'	1.386 (3)	C7—H7C	0.9800
C2'—H2'	0.9500	C7'—H7'	0.9500
C2—C3	1.400 (2)	C8—C9	1.527 (3)
C2—C8	1.513 (2)	C8—H8	1.0000
C3'—C4'	1.389 (3)	C9—H9A	0.9800
C3'—H3'	0.9500	C9—H9B	0.9800
C3—C4	1.380 (3)	C9—H9C	0.9800
C3—H3	0.9500	C10—O2	1.424 (3)
C4—O2	1.369 (2)	C10—H10A	0.9800
C4—C5	1.403 (3)	C10—H10B	0.9800
C4'—C6'	1.393 (3)	C10—H10C	0.9800
C4'—C5'	1.504 (3)	C11—H11A	0.9800
C5—C6	1.381 (3)	C11—H11B	0.9800
C5—C11	1.503 (3)	C11—H11C	0.9800
C5'—H5'1	0.9800	O1—S1	1.5967 (12)
C5'—H5'2	0.9800	O3—S1	1.4216 (14)
C5'—H5'3	0.9800	O4—S1	1.4221 (14)
C2—C1—C6	122.74 (16)	C8—C7—H7B	109.5
C2—C1—O1	118.38 (15)	H7A—C7—H7B	109.5
C6—C1—O1	118.64 (15)	C8—C7—H7C	109.5
C2'—C1'—C7'	120.86 (18)	H7A—C7—H7C	109.5
C2'—C1'—S1	120.13 (15)	H7B—C7—H7C	109.5
C7'—C1'—S1	119.00 (14)	C6'—C7'—C1'	119.26 (18)
C1'—C2'—C3'	118.97 (18)	C6'—C7'—H7'	120.4
C1'—C2'—H2'	120.5	C1'—C7'—H7'	120.4
C3'—C2'—H2'	120.5	C2—C8—C7	111.27 (16)
C1—C2—C3	116.24 (16)	C2—C8—C9	110.51 (17)
C1—C2—C8	123.71 (16)	C7—C8—C9	110.87 (17)
C3—C2—C8	120.05 (16)	C2—C8—H8	108.0
C2'—C3'—C4'	121.44 (18)	C7—C8—H8	108.0
C2'—C3'—H3'	119.3	C9—C8—H8	108.0
C4'—C3'—H3'	119.3	C8—C9—H9A	109.5
C4—C3—C2	121.63 (17)	C8—C9—H9B	109.5
C4—C3—H3	119.2	H9A—C9—H9B	109.5
C2—C3—H3	119.2	C8—C9—H9C	109.5
O2—C4—C3	123.76 (17)	H9A—C9—H9C	109.5
O2—C4—C5	114.99 (16)	H9B—C9—H9C	109.5
C3—C4—C5	121.26 (17)	O2—C10—H10A	109.5
C3'—C4'—C6'	118.20 (18)	O2—C10—H10B	109.5
C3'—C4'—C5'	121.55 (18)	H10A—C10—H10B	109.5
C6'—C4'—C5'	120.25 (18)	O2—C10—H10C	109.5
C6—C5—C4	117.33 (16)	H10A—C10—H10C	109.5
C6—C5—C11	121.84 (18)	H10B—C10—H10C	109.5
C4—C5—C11	120.83 (18)	C5—C11—H11A	109.5
C4'—C5'—H5'1	109.5	C5—C11—H11B	109.5
C4'—C5'—H5'2	109.5	H11A—C11—H11B	109.5
H5'1—C5'—H5'2	109.5	C5—C11—H11C	109.5
C4'—C5'—H5'3	109.5	H11A—C11—H11C	109.5
H5'1—C5'—H5'3	109.5	H11B—C11—H11C	109.5
H5'2—C5'—H5'3	109.5	C1—O1—S1	120.71 (11)
C5—C6—C1	120.79 (17)	C4—O2—C10	117.16 (15)
C5—C6—H6	119.6	O3—S1—O4	119.91 (9)
C1—C6—H6	119.6	O3—S1—O1	109.37 (8)
C7'—C6'—C4'	121.25 (18)	O4—S1—O1	102.77 (8)
C7'—C6'—H6'	119.4	O3—S1—C1'	109.08 (9)
C4'—C6'—H6'	119.4	O4—S1—C1'	109.79 (9)
C8—C7—H7A	109.5	O1—S1—C1'	104.76 (8)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the phenyl rings C1–C6 and C1'–C6', respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3′—H3′···O1^i	0.95	2.67	3.610 (2)	169
C5′—H5′3···O3^ii	0.98	2.66	3.589 (3)	159
C7—H7A···O4^iii	0.98	2.72	3.693 (3)	175
C10—H10B···O3^iv	0.98	2.61	3.317 (3)	130
C10—H10A···O4^iii	0.98	2.70	3.521 (3)	142
C5′—H5′2···Cg2^v	0.98	2.84	3.706	148
C11—H11B···Cg1^iv	0.98	2.75	3.635	150
C9—H9A···Cg2	0.98	2.70	3.5373	144

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x, −y, −z; (v) −x+1, −y, −z+1.