1,3-Di­methoxy-5-(tri­phenyl­methyl­thio)­benzene

Vande Velde, C.M.L.; Geise, H.J.; Blockhuys, F.

doi:10.1107/S1600536803019718

Buy article online - an online subscription or single-article purchase is required to access this article.

1,3-Dimethoxy-5-(triphenylmethylthio)benzene

C. M. L. Vande Velde, H. J. Geise and F. Blockhuys

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.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019718/cv6228sup1.cif Contains datablocks I, tpthio1
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019718/cv6228Isup2.hkl Contains datablock I

CCDC reference: 225771

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (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

C₂₇H₂₄O₂S	Z = 2
M_r = 412.52	F(000) = 436
Triclinic, P1	D_x = 1.286 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8390 (12) Å	Cell parameters from 25 reflections
b = 10.157 (4) Å	θ = 7.7–19.8°
c = 12.672 (2) Å	µ = 0.17 mm⁻¹
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	R_int = 0.018
Radiation source: fine-focus sealed tube	θ_max = 27.0°, θ_min = 1.7°
Graphite monochromator	h = 0→11
ω/2θ scans	k = −12→12
4949 measured reflections	l = −15→16
4635 independent reflections	3 standard reflections every 60 min
3417 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0502P)² + 0.227P] where P = (F_o² + 2F_c²)/3
4635 reflections	(Δ/σ)_max < 0.001
329 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

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

	x	y	z	U_iso*/U_eq
S1	0.26666 (5)	0.43771 (4)	0.31487 (3)	0.04133 (13)
C7	0.16204 (18)	0.26908 (15)	0.37706 (13)	0.0329 (3)
O3	0.32507 (19)	0.43316 (15)	−0.10604 (11)	0.0618 (4)
O5	0.0398 (2)	0.78053 (14)	0.06674 (13)	0.0657 (4)
C1	0.23071 (19)	0.49551 (16)	0.18359 (13)	0.0372 (4)
C6	0.1465 (2)	0.61168 (17)	0.17317 (15)	0.0422 (4)
H6	0.103 (2)	0.658 (2)	0.2350 (17)	0.051*
C14	−0.01881 (18)	0.28493 (15)	0.40584 (13)	0.0336 (3)
C9	0.2647 (2)	0.10056 (18)	0.51382 (15)	0.0427 (4)
H9	0.274 (2)	0.033 (2)	0.4659 (17)	0.051*
C8	0.21226 (18)	0.22839 (16)	0.48463 (13)	0.0354 (3)
C20	0.2248 (2)	0.16959 (16)	0.29712 (13)	0.0372 (4)
C25	0.1234 (3)	0.08015 (18)	0.27953 (16)	0.0458 (4)
H25	0.015 (3)	0.080 (2)	0.3185 (17)	0.055*
C5	0.1249 (2)	0.66527 (18)	0.06950 (16)	0.0465 (4)
C2	0.2960 (2)	0.43213 (18)	0.09059 (14)	0.0408 (4)
H2	0.356 (2)	0.353 (2)	0.0965 (16)	0.049*
C3	0.2702 (2)	0.48615 (19)	−0.01018 (15)	0.0446 (4)
C13	0.1984 (2)	0.31866 (19)	0.55818 (14)	0.0408 (4)
H13	0.162 (2)	0.408 (2)	0.5408 (16)	0.049*
C4	0.1852 (2)	0.6030 (2)	−0.02193 (16)	0.0487 (4)
H4	0.169 (2)	0.641 (2)	−0.0919 (19)	0.058*
C19	−0.0887 (2)	0.33482 (18)	0.32179 (15)	0.0417 (4)
H19	−0.023 (2)	0.3559 (19)	0.2435 (17)	0.050*
C21	0.3876 (2)	0.1613 (2)	0.24513 (17)	0.0511 (5)
H21	0.461 (3)	0.223 (2)	0.2586 (18)	0.061*
C12	0.2359 (2)	0.2803 (2)	0.65780 (15)	0.0478 (4)
H12	0.222 (2)	0.347 (2)	0.7073 (18)	0.057*
C18	−0.2514 (2)	0.3495 (2)	0.34740 (17)	0.0486 (4)
H18	−0.292 (2)	0.392 (2)	0.2874 (18)	0.058*
C11	0.2870 (2)	0.1526 (2)	0.68573 (16)	0.0522 (5)
H11	0.309 (3)	0.127 (2)	0.7533 (19)	0.063*
C15	−0.1186 (2)	0.24740 (19)	0.51449 (15)	0.0435 (4)
H15	−0.078 (2)	0.210 (2)	0.5712 (17)	0.052*
C10	0.3019 (2)	0.0628 (2)	0.61401 (17)	0.0519 (5)
H10	0.338 (3)	−0.024 (2)	0.6316 (18)	0.062*
C24	0.1823 (3)	−0.0128 (2)	0.20969 (18)	0.0615 (6)
H24	0.108 (3)	−0.069 (2)	0.199 (2)	0.074*
C16	−0.2817 (2)	0.2610 (2)	0.53947 (18)	0.0553 (5)
H16	−0.345 (3)	0.237 (2)	0.612 (2)	0.066*
C23	0.3418 (4)	−0.0167 (2)	0.15647 (19)	0.0713 (7)
H23	0.380 (3)	−0.077 (3)	0.106 (2)	0.086*
C17	−0.3483 (2)	0.3128 (2)	0.45655 (18)	0.0536 (5)
H17	−0.459 (3)	0.322 (2)	0.4724 (18)	0.064*
C26	0.4176 (3)	0.3167 (2)	−0.10240 (18)	0.0571 (5)
H26A	0.5074 (16)	0.3327 (6)	−0.0749 (13)	0.086*
H26B	0.4589 (16)	0.2950 (9)	−0.1787 (11)	0.086*
H26C	0.3512 (10)	0.2410 (11)	−0.0510 (12)	0.086*
C22	0.4440 (3)	0.0692 (3)	0.17502 (19)	0.0691 (7)
H22	0.552 (3)	0.073 (3)	0.139 (2)	0.083*
C27	0.0015 (3)	0.8311 (2)	−0.0340 (2)	0.0690 (6)
H27A	0.1001 (15)	0.8621 (17)	−0.0956 (10)	0.104*
H27B	−0.071 (2)	0.9072 (16)	−0.0222 (5)	0.104*
H27C	−0.051 (2)	0.7592 (12)	−0.0546 (9)	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0481 (2)	0.0409 (2)	0.0374 (2)	−0.00677 (18)	−0.01659 (18)	−0.00541 (17)
C7	0.0336 (8)	0.0340 (8)	0.0322 (8)	0.0008 (6)	−0.0113 (6)	−0.0066 (6)
O3	0.0830 (10)	0.0660 (9)	0.0397 (7)	0.0225 (8)	−0.0201 (7)	−0.0192 (6)
O5	0.0938 (11)	0.0517 (8)	0.0666 (9)	0.0292 (8)	−0.0442 (9)	−0.0196 (7)
C1	0.0385 (9)	0.0374 (8)	0.0346 (8)	−0.0037 (7)	−0.0108 (7)	−0.0037 (6)
C6	0.0457 (10)	0.0399 (9)	0.0425 (9)	0.0022 (7)	−0.0135 (8)	−0.0114 (7)
C14	0.0335 (8)	0.0321 (8)	0.0373 (8)	0.0027 (6)	−0.0124 (6)	−0.0087 (6)
C9	0.0481 (10)	0.0408 (9)	0.0435 (9)	0.0046 (7)	−0.0197 (8)	−0.0093 (7)
C8	0.0305 (7)	0.0420 (9)	0.0341 (8)	0.0022 (6)	−0.0110 (6)	−0.0064 (6)
C20	0.0445 (9)	0.0356 (8)	0.0330 (8)	0.0088 (7)	−0.0151 (7)	−0.0062 (6)
C25	0.0600 (11)	0.0397 (9)	0.0437 (10)	0.0068 (8)	−0.0233 (9)	−0.0108 (7)
C5	0.0533 (10)	0.0395 (9)	0.0516 (10)	0.0061 (8)	−0.0225 (8)	−0.0104 (8)
C2	0.0430 (9)	0.0390 (9)	0.0384 (9)	0.0030 (7)	−0.0100 (7)	−0.0062 (7)
C3	0.0480 (10)	0.0466 (10)	0.0388 (9)	0.0018 (8)	−0.0104 (7)	−0.0115 (7)
C13	0.0416 (9)	0.0451 (10)	0.0387 (9)	0.0076 (7)	−0.0151 (7)	−0.0112 (7)
C4	0.0587 (11)	0.0495 (10)	0.0413 (10)	0.0058 (8)	−0.0218 (9)	−0.0064 (8)
C19	0.0383 (9)	0.0474 (10)	0.0399 (9)	0.0004 (7)	−0.0146 (7)	−0.0045 (7)
C21	0.0480 (11)	0.0558 (11)	0.0480 (10)	0.0172 (9)	−0.0135 (8)	−0.0103 (9)
C12	0.0501 (10)	0.0585 (11)	0.0404 (9)	0.0062 (8)	−0.0190 (8)	−0.0150 (8)
C18	0.0419 (10)	0.0530 (11)	0.0552 (11)	0.0041 (8)	−0.0228 (9)	−0.0073 (9)
C11	0.0568 (11)	0.0645 (12)	0.0413 (10)	0.0050 (9)	−0.0271 (9)	−0.0042 (9)
C15	0.0391 (9)	0.0534 (10)	0.0378 (9)	0.0002 (8)	−0.0125 (7)	−0.0061 (8)
C10	0.0597 (12)	0.0470 (11)	0.0523 (11)	0.0089 (9)	−0.0275 (9)	−0.0007 (9)
C24	0.1038 (19)	0.0397 (10)	0.0571 (12)	0.0173 (11)	−0.0444 (13)	−0.0179 (9)
C16	0.0389 (10)	0.0769 (14)	0.0450 (10)	−0.0010 (9)	−0.0043 (8)	−0.0124 (10)
C23	0.114 (2)	0.0576 (13)	0.0501 (12)	0.0445 (14)	−0.0329 (13)	−0.0236 (10)
C17	0.0326 (9)	0.0663 (13)	0.0640 (13)	0.0059 (8)	−0.0137 (9)	−0.0196 (10)
C26	0.0575 (12)	0.0596 (12)	0.0548 (12)	0.0077 (10)	−0.0109 (9)	−0.0237 (10)
C22	0.0722 (15)	0.0773 (16)	0.0514 (12)	0.0423 (13)	−0.0118 (11)	−0.0156 (11)
C27	0.0881 (17)	0.0545 (12)	0.0798 (16)	0.0184 (11)	−0.0504 (14)	−0.0112 (11)

Geometric parameters (Å, º) top

S1—C1	1.7777 (17)	C4—H4	0.95 (2)
S1—C7	1.8928 (17)	C19—C18	1.383 (2)
C7—C20	1.533 (2)	C19—H19	0.97 (2)
C7—C14	1.537 (2)	C21—C22	1.385 (3)
C7—C8	1.540 (2)	C21—H21	0.99 (2)
O3—C3	1.366 (2)	C12—C11	1.377 (3)
O3—C26	1.416 (2)	C12—H12	0.98 (2)
O5—C5	1.369 (2)	C18—C17	1.378 (3)
O5—C27	1.420 (2)	C18—H18	0.96 (2)
C1—C6	1.379 (2)	C11—C10	1.378 (3)
C1—C2	1.406 (2)	C11—H11	0.92 (2)
C6—C5	1.393 (3)	C15—C16	1.386 (3)
C6—H6	0.96 (2)	C15—H15	0.92 (2)
C14—C15	1.382 (2)	C10—H10	0.94 (2)
C14—C19	1.397 (2)	C24—C23	1.369 (4)
C9—C8	1.386 (2)	C24—H24	0.95 (2)
C9—C10	1.390 (2)	C16—C17	1.370 (3)
C9—H9	0.98 (2)	C16—H16	0.91 (2)
C8—C13	1.401 (2)	C23—C22	1.376 (4)
C20—C25	1.390 (3)	C23—H23	0.94 (3)
C20—C21	1.395 (3)	C17—H17	0.94 (2)
C25—C24	1.392 (3)	C26—H26A	0.9874
C25—H25	0.94 (2)	C26—H26B	0.9874
C5—C4	1.377 (3)	C26—H26C	0.9874
C2—C3	1.376 (2)	C22—H22	0.92 (3)
C2—H2	0.95 (2)	C27—H27A	0.9917
C3—C4	1.391 (3)	C27—H27B	0.9917
C13—C12	1.385 (2)	C27—H27C	0.9917
C13—H13	0.96 (2)

C1—S1—C7	107.65 (7)	C14—C19—H19	119.6 (12)
C20—C7—C14	112.50 (12)	C22—C21—C20	120.2 (2)
C20—C7—C8	110.45 (13)	C22—C21—H21	120.9 (13)
C14—C7—C8	111.11 (12)	C20—C21—H21	118.9 (13)
C20—C7—S1	110.35 (11)	C11—C12—C13	120.28 (18)
C14—C7—S1	110.23 (11)	C11—C12—H12	122.5 (12)
C8—C7—S1	101.69 (10)	C13—C12—H12	117.2 (12)
C3—O3—C26	117.96 (15)	C17—C18—C19	120.49 (18)
C5—O5—C27	117.19 (16)	C17—C18—H18	121.9 (13)
C6—C1—C2	120.67 (15)	C19—C18—H18	117.4 (13)
C6—C1—S1	117.50 (13)	C12—C11—C10	119.92 (17)
C2—C1—S1	121.63 (13)	C12—C11—H11	119.6 (14)
C1—C6—C5	119.31 (16)	C10—C11—H11	120.5 (14)
C1—C6—H6	122.1 (12)	C14—C15—C16	121.26 (17)
C5—C6—H6	118.6 (12)	C14—C15—H15	120.1 (12)
C15—C14—C19	117.51 (15)	C16—C15—H15	118.6 (13)
C15—C14—C7	121.67 (14)	C11—C10—C9	120.18 (18)
C19—C14—C7	120.79 (14)	C11—C10—H10	120.9 (13)
C8—C9—C10	120.70 (17)	C9—C10—H10	118.9 (14)
C8—C9—H9	121.5 (12)	C23—C24—C25	120.2 (2)
C10—C9—H9	117.8 (12)	C23—C24—H24	122.5 (15)
C9—C8—C13	118.44 (15)	C25—C24—H24	117.3 (15)
C9—C8—C7	121.21 (14)	C17—C16—C15	120.59 (19)
C13—C8—C7	120.28 (14)	C17—C16—H16	119.7 (15)
C25—C20—C21	118.15 (17)	C15—C16—H16	119.6 (15)
C25—C20—C7	121.40 (15)	C24—C23—C22	119.6 (2)
C21—C20—C7	120.34 (15)	C24—C23—H23	119.4 (16)
C20—C25—C24	120.9 (2)	C22—C23—H23	121.1 (16)
C20—C25—H25	119.1 (13)	C16—C17—C18	119.17 (17)
C24—C25—H25	119.9 (13)	C16—C17—H17	121.3 (14)
O5—C5—C4	123.75 (17)	C18—C17—H17	119.5 (14)
O5—C5—C6	115.43 (16)	O3—C26—H26A	109.5
C4—C5—C6	120.82 (17)	O3—C26—H26B	109.5
C3—C2—C1	118.63 (16)	H26A—C26—H26B	109.5
C3—C2—H2	120.0 (12)	O3—C26—H26C	109.5
C1—C2—H2	121.4 (12)	H26A—C26—H26C	109.5
O3—C3—C2	124.31 (17)	H26B—C26—H26C	109.5
O3—C3—C4	114.35 (16)	C23—C22—C21	121.0 (2)
C2—C3—C4	121.34 (17)	C23—C22—H22	122.7 (17)
C12—C13—C8	120.48 (17)	C21—C22—H22	116.2 (17)
C12—C13—H13	118.7 (12)	O5—C27—H27A	109.5
C8—C13—H13	120.8 (12)	O5—C27—H27B	109.5
C5—C4—C3	119.19 (17)	H27A—C27—H27B	109.5
C5—C4—H4	119.8 (13)	O5—C27—H27C	109.5
C3—C4—H4	121.0 (13)	H27A—C27—H27C	109.5
C18—C19—C14	120.96 (17)	H27B—C27—H27C	109.5
C18—C19—H19	119.4 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg(C)ⁱ	0.96 (2)	3.913 (3)	3.09 (2)	144.5 (14)
C17—H17···Cg(B)ⁱⁱ	0.94 (2)	3.585 (3)	2.78 (3)	143.1 (17)
C26—H26a···Cg(A)ⁱⁱⁱ	0.99	3.72 (1)	2.797 (15)	157

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page