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The title compound, C27H24O2S, crystallizes in space group P\overline1 with one mol­ecule in the asymmetric unit. The geometry and intermolecular contacts are described: the rings in thetriphenylmethyl moiety show a near-threefold symmetry, and the compound displays OCH3–π interactions in the methoxy-substituted ring and herringbone interactions between the unsubstituted rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019718/cv6228sup1.cif
Contains datablocks I, tpthio1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019718/cv6228Isup2.hkl
Contains datablock I

CCDC reference: 225771

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.113
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H26A PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H26B PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H26C PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H27A PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H27B PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H27C
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

S-(3,5-dimethoxyphenyl)-triphenylmethanethiolate top
Crystal data top
C27H24O2SZ = 2
Mr = 412.52F(000) = 436
Triclinic, P1Dx = 1.286 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8390 (12) ÅCell parameters from 25 reflections
b = 10.157 (4) Åθ = 7.7–19.8°
c = 12.672 (2) ŵ = 0.17 mm1
α = 79.37 (2)°T = 293 K
β = 72.31 (2)°Block, colourless
γ = 87.93 (2)°0.40 × 0.23 × 0.20 mm
V = 1065.0 (5) Å3
Data collection top
Enraf-Nonius Mach3
diffractometer
Rint = 0.018
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 1.7°
Graphite monochromatorh = 011
ω/2θ scansk = 1212
4949 measured reflectionsl = 1516
4635 independent reflections3 standard reflections every 60 min
3417 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0502P)2 + 0.227P]
where P = (Fo2 + 2Fc2)/3
4635 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.26666 (5)0.43771 (4)0.31487 (3)0.04133 (13)
C70.16204 (18)0.26908 (15)0.37706 (13)0.0329 (3)
O30.32507 (19)0.43316 (15)0.10604 (11)0.0618 (4)
O50.0398 (2)0.78053 (14)0.06674 (13)0.0657 (4)
C10.23071 (19)0.49551 (16)0.18359 (13)0.0372 (4)
C60.1465 (2)0.61168 (17)0.17317 (15)0.0422 (4)
H60.103 (2)0.658 (2)0.2350 (17)0.051*
C140.01881 (18)0.28493 (15)0.40584 (13)0.0336 (3)
C90.2647 (2)0.10056 (18)0.51382 (15)0.0427 (4)
H90.274 (2)0.033 (2)0.4659 (17)0.051*
C80.21226 (18)0.22839 (16)0.48463 (13)0.0354 (3)
C200.2248 (2)0.16959 (16)0.29712 (13)0.0372 (4)
C250.1234 (3)0.08015 (18)0.27953 (16)0.0458 (4)
H250.015 (3)0.080 (2)0.3185 (17)0.055*
C50.1249 (2)0.66527 (18)0.06950 (16)0.0465 (4)
C20.2960 (2)0.43213 (18)0.09059 (14)0.0408 (4)
H20.356 (2)0.353 (2)0.0965 (16)0.049*
C30.2702 (2)0.48615 (19)0.01018 (15)0.0446 (4)
C130.1984 (2)0.31866 (19)0.55818 (14)0.0408 (4)
H130.162 (2)0.408 (2)0.5408 (16)0.049*
C40.1852 (2)0.6030 (2)0.02193 (16)0.0487 (4)
H40.169 (2)0.641 (2)0.0919 (19)0.058*
C190.0887 (2)0.33482 (18)0.32179 (15)0.0417 (4)
H190.023 (2)0.3559 (19)0.2435 (17)0.050*
C210.3876 (2)0.1613 (2)0.24513 (17)0.0511 (5)
H210.461 (3)0.223 (2)0.2586 (18)0.061*
C120.2359 (2)0.2803 (2)0.65780 (15)0.0478 (4)
H120.222 (2)0.347 (2)0.7073 (18)0.057*
C180.2514 (2)0.3495 (2)0.34740 (17)0.0486 (4)
H180.292 (2)0.392 (2)0.2874 (18)0.058*
C110.2870 (2)0.1526 (2)0.68573 (16)0.0522 (5)
H110.309 (3)0.127 (2)0.7533 (19)0.063*
C150.1186 (2)0.24740 (19)0.51449 (15)0.0435 (4)
H150.078 (2)0.210 (2)0.5712 (17)0.052*
C100.3019 (2)0.0628 (2)0.61401 (17)0.0519 (5)
H100.338 (3)0.024 (2)0.6316 (18)0.062*
C240.1823 (3)0.0128 (2)0.20969 (18)0.0615 (6)
H240.108 (3)0.069 (2)0.199 (2)0.074*
C160.2817 (2)0.2610 (2)0.53947 (18)0.0553 (5)
H160.345 (3)0.237 (2)0.612 (2)0.066*
C230.3418 (4)0.0167 (2)0.15647 (19)0.0713 (7)
H230.380 (3)0.077 (3)0.106 (2)0.086*
C170.3483 (2)0.3128 (2)0.45655 (18)0.0536 (5)
H170.459 (3)0.322 (2)0.4724 (18)0.064*
C260.4176 (3)0.3167 (2)0.10240 (18)0.0571 (5)
H26A0.5074 (16)0.3327 (6)0.0749 (13)0.086*
H26B0.4589 (16)0.2950 (9)0.1787 (11)0.086*
H26C0.3512 (10)0.2410 (11)0.0510 (12)0.086*
C220.4440 (3)0.0692 (3)0.17502 (19)0.0691 (7)
H220.552 (3)0.073 (3)0.139 (2)0.083*
C270.0015 (3)0.8311 (2)0.0340 (2)0.0690 (6)
H27A0.1001 (15)0.8621 (17)0.0956 (10)0.104*
H27B0.071 (2)0.9072 (16)0.0222 (5)0.104*
H27C0.051 (2)0.7592 (12)0.0546 (9)0.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0481 (2)0.0409 (2)0.0374 (2)0.00677 (18)0.01659 (18)0.00541 (17)
C70.0336 (8)0.0340 (8)0.0322 (8)0.0008 (6)0.0113 (6)0.0066 (6)
O30.0830 (10)0.0660 (9)0.0397 (7)0.0225 (8)0.0201 (7)0.0192 (6)
O50.0938 (11)0.0517 (8)0.0666 (9)0.0292 (8)0.0442 (9)0.0196 (7)
C10.0385 (9)0.0374 (8)0.0346 (8)0.0037 (7)0.0108 (7)0.0037 (6)
C60.0457 (10)0.0399 (9)0.0425 (9)0.0022 (7)0.0135 (8)0.0114 (7)
C140.0335 (8)0.0321 (8)0.0373 (8)0.0027 (6)0.0124 (6)0.0087 (6)
C90.0481 (10)0.0408 (9)0.0435 (9)0.0046 (7)0.0197 (8)0.0093 (7)
C80.0305 (7)0.0420 (9)0.0341 (8)0.0022 (6)0.0110 (6)0.0064 (6)
C200.0445 (9)0.0356 (8)0.0330 (8)0.0088 (7)0.0151 (7)0.0062 (6)
C250.0600 (11)0.0397 (9)0.0437 (10)0.0068 (8)0.0233 (9)0.0108 (7)
C50.0533 (10)0.0395 (9)0.0516 (10)0.0061 (8)0.0225 (8)0.0104 (8)
C20.0430 (9)0.0390 (9)0.0384 (9)0.0030 (7)0.0100 (7)0.0062 (7)
C30.0480 (10)0.0466 (10)0.0388 (9)0.0018 (8)0.0104 (7)0.0115 (7)
C130.0416 (9)0.0451 (10)0.0387 (9)0.0076 (7)0.0151 (7)0.0112 (7)
C40.0587 (11)0.0495 (10)0.0413 (10)0.0058 (8)0.0218 (9)0.0064 (8)
C190.0383 (9)0.0474 (10)0.0399 (9)0.0004 (7)0.0146 (7)0.0045 (7)
C210.0480 (11)0.0558 (11)0.0480 (10)0.0172 (9)0.0135 (8)0.0103 (9)
C120.0501 (10)0.0585 (11)0.0404 (9)0.0062 (8)0.0190 (8)0.0150 (8)
C180.0419 (10)0.0530 (11)0.0552 (11)0.0041 (8)0.0228 (9)0.0073 (9)
C110.0568 (11)0.0645 (12)0.0413 (10)0.0050 (9)0.0271 (9)0.0042 (9)
C150.0391 (9)0.0534 (10)0.0378 (9)0.0002 (8)0.0125 (7)0.0061 (8)
C100.0597 (12)0.0470 (11)0.0523 (11)0.0089 (9)0.0275 (9)0.0007 (9)
C240.1038 (19)0.0397 (10)0.0571 (12)0.0173 (11)0.0444 (13)0.0179 (9)
C160.0389 (10)0.0769 (14)0.0450 (10)0.0010 (9)0.0043 (8)0.0124 (10)
C230.114 (2)0.0576 (13)0.0501 (12)0.0445 (14)0.0329 (13)0.0236 (10)
C170.0326 (9)0.0663 (13)0.0640 (13)0.0059 (8)0.0137 (9)0.0196 (10)
C260.0575 (12)0.0596 (12)0.0548 (12)0.0077 (10)0.0109 (9)0.0237 (10)
C220.0722 (15)0.0773 (16)0.0514 (12)0.0423 (13)0.0118 (11)0.0156 (11)
C270.0881 (17)0.0545 (12)0.0798 (16)0.0184 (11)0.0504 (14)0.0112 (11)
Geometric parameters (Å, º) top
S1—C11.7777 (17)C4—H40.95 (2)
S1—C71.8928 (17)C19—C181.383 (2)
C7—C201.533 (2)C19—H190.97 (2)
C7—C141.537 (2)C21—C221.385 (3)
C7—C81.540 (2)C21—H210.99 (2)
O3—C31.366 (2)C12—C111.377 (3)
O3—C261.416 (2)C12—H120.98 (2)
O5—C51.369 (2)C18—C171.378 (3)
O5—C271.420 (2)C18—H180.96 (2)
C1—C61.379 (2)C11—C101.378 (3)
C1—C21.406 (2)C11—H110.92 (2)
C6—C51.393 (3)C15—C161.386 (3)
C6—H60.96 (2)C15—H150.92 (2)
C14—C151.382 (2)C10—H100.94 (2)
C14—C191.397 (2)C24—C231.369 (4)
C9—C81.386 (2)C24—H240.95 (2)
C9—C101.390 (2)C16—C171.370 (3)
C9—H90.98 (2)C16—H160.91 (2)
C8—C131.401 (2)C23—C221.376 (4)
C20—C251.390 (3)C23—H230.94 (3)
C20—C211.395 (3)C17—H170.94 (2)
C25—C241.392 (3)C26—H26A0.9874
C25—H250.94 (2)C26—H26B0.9874
C5—C41.377 (3)C26—H26C0.9874
C2—C31.376 (2)C22—H220.92 (3)
C2—H20.95 (2)C27—H27A0.9917
C3—C41.391 (3)C27—H27B0.9917
C13—C121.385 (2)C27—H27C0.9917
C13—H130.96 (2)
C1—S1—C7107.65 (7)C14—C19—H19119.6 (12)
C20—C7—C14112.50 (12)C22—C21—C20120.2 (2)
C20—C7—C8110.45 (13)C22—C21—H21120.9 (13)
C14—C7—C8111.11 (12)C20—C21—H21118.9 (13)
C20—C7—S1110.35 (11)C11—C12—C13120.28 (18)
C14—C7—S1110.23 (11)C11—C12—H12122.5 (12)
C8—C7—S1101.69 (10)C13—C12—H12117.2 (12)
C3—O3—C26117.96 (15)C17—C18—C19120.49 (18)
C5—O5—C27117.19 (16)C17—C18—H18121.9 (13)
C6—C1—C2120.67 (15)C19—C18—H18117.4 (13)
C6—C1—S1117.50 (13)C12—C11—C10119.92 (17)
C2—C1—S1121.63 (13)C12—C11—H11119.6 (14)
C1—C6—C5119.31 (16)C10—C11—H11120.5 (14)
C1—C6—H6122.1 (12)C14—C15—C16121.26 (17)
C5—C6—H6118.6 (12)C14—C15—H15120.1 (12)
C15—C14—C19117.51 (15)C16—C15—H15118.6 (13)
C15—C14—C7121.67 (14)C11—C10—C9120.18 (18)
C19—C14—C7120.79 (14)C11—C10—H10120.9 (13)
C8—C9—C10120.70 (17)C9—C10—H10118.9 (14)
C8—C9—H9121.5 (12)C23—C24—C25120.2 (2)
C10—C9—H9117.8 (12)C23—C24—H24122.5 (15)
C9—C8—C13118.44 (15)C25—C24—H24117.3 (15)
C9—C8—C7121.21 (14)C17—C16—C15120.59 (19)
C13—C8—C7120.28 (14)C17—C16—H16119.7 (15)
C25—C20—C21118.15 (17)C15—C16—H16119.6 (15)
C25—C20—C7121.40 (15)C24—C23—C22119.6 (2)
C21—C20—C7120.34 (15)C24—C23—H23119.4 (16)
C20—C25—C24120.9 (2)C22—C23—H23121.1 (16)
C20—C25—H25119.1 (13)C16—C17—C18119.17 (17)
C24—C25—H25119.9 (13)C16—C17—H17121.3 (14)
O5—C5—C4123.75 (17)C18—C17—H17119.5 (14)
O5—C5—C6115.43 (16)O3—C26—H26A109.5
C4—C5—C6120.82 (17)O3—C26—H26B109.5
C3—C2—C1118.63 (16)H26A—C26—H26B109.5
C3—C2—H2120.0 (12)O3—C26—H26C109.5
C1—C2—H2121.4 (12)H26A—C26—H26C109.5
O3—C3—C2124.31 (17)H26B—C26—H26C109.5
O3—C3—C4114.35 (16)C23—C22—C21121.0 (2)
C2—C3—C4121.34 (17)C23—C22—H22122.7 (17)
C12—C13—C8120.48 (17)C21—C22—H22116.2 (17)
C12—C13—H13118.7 (12)O5—C27—H27A109.5
C8—C13—H13120.8 (12)O5—C27—H27B109.5
C5—C4—C3119.19 (17)H27A—C27—H27B109.5
C5—C4—H4119.8 (13)O5—C27—H27C109.5
C3—C4—H4121.0 (13)H27A—C27—H27C109.5
C18—C19—C14120.96 (17)H27B—C27—H27C109.5
C18—C19—H19119.4 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···Cg(C)i0.96 (2)3.913 (3)3.09 (2)144.5 (14)
C17—H17···Cg(B)ii0.94 (2)3.585 (3)2.78 (3)143.1 (17)
C26—H26a···Cg(A)iii0.993.72 (1)2.797 (15)157
Symmetry codes: (i) x, y+1, z+1; (ii) x1, y, z; (iii) x+1, y+1, z.
 

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