2-Meth-oxy-4-methyl-phenyl 4-toluene-sulfonate.

In the title mol-ecule, C(15)H(16)O(4)S, the inter-planar angle between the two aromatic rings is 45.07 (7)°. The crystal packing is stabilized by weak inter-molecular C-H⋯O inter-actions.

Related literature

For related literature, see: Manivannan et al. (2005a ▶); Spungin et al. (1984 ▶); Yachi et al. (1989 ▶). Similar compounds have been reported by: Manivannan et al. (2005b ▶); Ramachandran et al.(2007 ▶).

Experimental

Crystal data

C15H16O4S

M = 292.34

Triclinic,

a = 7.932 (2) Å

b = 8.736 (3) Å

c = 10.934 (3) Å

α = 93.785 (5)°

β = 98.453 (5)°

γ = 102.476 (4)°

V = 727.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 293 (2) K

0.48 × 0.46 × 0.14 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.902, T max = 0.970

8439 measured reflections

3348 independent reflections

2220 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.140

S = 1.02

3348 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025749/bt2764sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025749/bt2764Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H16O4S	Z = 2
Mr = 292.34	F000 = 308
Triclinic, P1	Dx = 1.334 Mg m−3
a = 7.932 (2) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.736 (3) Å	Cell parameters from 2654 reflections
c = 10.934 (3) Å	θ = 1.9–24.7º
α = 93.785 (5)º	µ = 0.23 mm−1
β = 98.453 (5)º	T = 293 (2) K
γ = 102.476 (4)º	Block, colourless
V = 727.9 (4) Å3	0.48 × 0.46 × 0.14 mm

Bruker KappaAPEX2 diffractometer	3348 independent reflections
Radiation source: fine-focus sealed tube	2220 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 293(2) K	θmax = 28.0º
ω and φ scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.902, Tmax = 0.970	k = −11→11
8439 measured reflections	l = −13→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0612P)2 + 0.2027P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3348 reflections	Δρmax = 0.30 e Å−3
184 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
S1	0.14427 (8)	0.00747 (7)	0.26949 (6)	0.0589 (2)
O3	0.02375 (19)	−0.13695 (17)	0.32049 (15)	0.0545 (4)
C1	0.2907 (3)	−0.0764 (2)	0.1975 (2)	0.0494 (5)
O4	0.0552 (2)	−0.41635 (18)	0.23259 (14)	0.0597 (4)
C13	0.1215 (3)	−0.3741 (2)	0.3550 (2)	0.0460 (5)
C12	0.2000 (3)	−0.4645 (3)	0.4347 (2)	0.0538 (6)
H12	0.2116	−0.5631	0.4044	0.065*
O1	0.0236 (3)	0.0562 (2)	0.17935 (19)	0.0802 (6)
C8	0.1067 (3)	−0.2266 (2)	0.4028 (2)	0.0475 (5)
O2	0.2394 (2)	0.11439 (19)	0.37184 (19)	0.0777 (6)
C6	0.4487 (3)	−0.0852 (3)	0.2655 (2)	0.0572 (6)
H6	0.4773	−0.0476	0.3492	0.069*
C5	0.5639 (3)	−0.1506 (3)	0.2077 (2)	0.0616 (6)
H5	0.6705	−0.1567	0.2533	0.074*
C9	0.1631 (3)	−0.1736 (3)	0.5253 (2)	0.0626 (7)
H9	0.1489	−0.0762	0.5561	0.075*
C11	0.2616 (3)	−0.4110 (3)	0.5584 (2)	0.0629 (7)
C2	0.2475 (3)	−0.1326 (3)	0.0737 (2)	0.0637 (7)
H2	0.1408	−0.1269	0.0280	0.076*
C4	0.5240 (3)	−0.2066 (3)	0.0845 (3)	0.0608 (6)
C10	0.2412 (4)	−0.2652 (4)	0.6028 (2)	0.0706 (7)
H10	0.2808	−0.2287	0.6862	0.085*
C3	0.3654 (4)	−0.1975 (3)	0.0186 (3)	0.0726 (8)
H3	0.3368	−0.2358	−0.0650	0.087*
C7	0.6524 (4)	−0.2766 (4)	0.0219 (3)	0.0907 (10)
H7A	0.6063	−0.3878	0.0013	0.136*
H7B	0.7620	−0.2589	0.0773	0.136*
H7C	0.6702	−0.2274	−0.0526	0.136*
C14	0.3479 (4)	−0.5125 (4)	0.6429 (3)	0.0940 (10)
H14A	0.4638	−0.4553	0.6794	0.141*
H14B	0.3544	−0.6069	0.5955	0.141*
H14C	0.2802	−0.5397	0.7075	0.141*
C15	0.0926 (5)	−0.5547 (4)	0.1778 (3)	0.0943 (10)
H15A	0.2171	−0.5422	0.1858	0.141*
H15B	0.0416	−0.5717	0.0913	0.141*
H15C	0.0444	−0.6435	0.2191	0.141*

	U11	U22	U33	U12	U13	U23
S1	0.0625 (4)	0.0381 (3)	0.0820 (5)	0.0201 (3)	0.0184 (3)	0.0062 (3)
O3	0.0500 (9)	0.0452 (8)	0.0746 (11)	0.0201 (7)	0.0160 (8)	0.0087 (7)
C1	0.0540 (13)	0.0374 (11)	0.0601 (14)	0.0134 (10)	0.0137 (11)	0.0086 (10)
O4	0.0777 (11)	0.0461 (9)	0.0574 (10)	0.0216 (8)	0.0090 (8)	0.0003 (7)
C13	0.0429 (11)	0.0438 (11)	0.0540 (13)	0.0108 (9)	0.0157 (10)	0.0054 (10)
C12	0.0507 (13)	0.0521 (13)	0.0676 (16)	0.0201 (11)	0.0225 (12)	0.0156 (11)
O1	0.0841 (13)	0.0644 (11)	0.1083 (15)	0.0442 (10)	0.0178 (11)	0.0297 (11)
C8	0.0453 (12)	0.0447 (11)	0.0562 (14)	0.0143 (9)	0.0138 (10)	0.0058 (10)
O2	0.0839 (13)	0.0459 (9)	0.1019 (14)	0.0120 (9)	0.0253 (11)	−0.0149 (9)
C6	0.0562 (14)	0.0547 (14)	0.0599 (15)	0.0118 (11)	0.0095 (12)	0.0019 (11)
C5	0.0524 (14)	0.0618 (15)	0.0749 (17)	0.0186 (12)	0.0144 (12)	0.0111 (13)
C9	0.0694 (16)	0.0578 (14)	0.0625 (16)	0.0150 (13)	0.0202 (13)	−0.0029 (12)
C11	0.0477 (13)	0.0779 (18)	0.0681 (17)	0.0152 (12)	0.0168 (12)	0.0248 (14)
C2	0.0634 (15)	0.0665 (16)	0.0623 (16)	0.0202 (13)	0.0043 (12)	0.0113 (13)
C4	0.0647 (16)	0.0496 (13)	0.0744 (17)	0.0145 (12)	0.0282 (13)	0.0106 (12)
C10	0.0700 (17)	0.0835 (19)	0.0542 (15)	0.0089 (15)	0.0104 (13)	0.0046 (14)
C3	0.090 (2)	0.0742 (18)	0.0568 (16)	0.0194 (16)	0.0220 (15)	0.0027 (13)
C7	0.093 (2)	0.080 (2)	0.114 (3)	0.0278 (18)	0.056 (2)	0.0064 (18)
C14	0.0724 (19)	0.129 (3)	0.092 (2)	0.036 (2)	0.0139 (17)	0.052 (2)
C15	0.144 (3)	0.0675 (18)	0.075 (2)	0.045 (2)	0.0110 (19)	−0.0157 (15)

S1—O2	1.4154 (19)	C9—H9	0.9300
S1—O1	1.4219 (19)	C11—C10	1.383 (4)
S1—O3	1.5954 (17)	C11—C14	1.514 (4)
S1—C1	1.751 (2)	C2—C3	1.382 (4)
O3—C8	1.414 (3)	C2—H2	0.9300
C1—C2	1.376 (3)	C4—C3	1.376 (4)
C1—C6	1.380 (3)	C4—C7	1.516 (3)
O4—C13	1.360 (3)	C10—H10	0.9300
O4—C15	1.421 (3)	C3—H3	0.9300
C13—C12	1.383 (3)	C7—H7A	0.9600
C13—C8	1.393 (3)	C7—H7B	0.9600
C12—C11	1.382 (3)	C7—H7C	0.9600
C12—H12	0.9300	C14—H14A	0.9600
C8—C9	1.364 (3)	C14—H14B	0.9600
C6—C5	1.381 (3)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C5—C4	1.369 (4)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C9—C10	1.376 (4)
O2—S1—O1	120.05 (12)	C10—C11—C14	121.2 (3)
O2—S1—O3	108.67 (11)	C1—C2—C3	118.8 (2)
O1—S1—O3	102.79 (10)	C1—C2—H2	120.6
O2—S1—C1	108.96 (11)	C3—C2—H2	120.6
O1—S1—C1	110.55 (12)	C5—C4—C3	118.6 (2)
O3—S1—C1	104.58 (9)	C5—C4—C7	120.7 (3)
C8—O3—S1	117.90 (13)	C3—C4—C7	120.7 (3)
C2—C1—C6	120.6 (2)	C9—C10—C11	120.9 (2)
C2—C1—S1	119.77 (18)	C9—C10—H10	119.6
C6—C1—S1	119.66 (18)	C11—C10—H10	119.6
C13—O4—C15	116.8 (2)	C4—C3—C2	121.5 (2)
O4—C13—C12	125.8 (2)	C4—C3—H3	119.2
O4—C13—C8	116.1 (2)	C2—C3—H3	119.2
C12—C13—C8	118.1 (2)	C4—C7—H7A	109.5
C11—C12—C13	121.2 (2)	C4—C7—H7B	109.5
C11—C12—H12	119.4	H7A—C7—H7B	109.5
C13—C12—H12	119.4	C4—C7—H7C	109.5
C9—C8—C13	121.4 (2)	H7A—C7—H7C	109.5
C9—C8—O3	121.2 (2)	H7B—C7—H7C	109.5
C13—C8—O3	117.30 (19)	C11—C14—H14A	109.5
C1—C6—C5	119.3 (2)	C11—C14—H14B	109.5
C1—C6—H6	120.4	H14A—C14—H14B	109.5
C5—C6—H6	120.4	C11—C14—H14C	109.5
C4—C5—C6	121.2 (2)	H14A—C14—H14C	109.5
C4—C5—H5	119.4	H14B—C14—H14C	109.5
C6—C5—H5	119.4	O4—C15—H15A	109.5
C8—C9—C10	119.5 (2)	O4—C15—H15B	109.5
C8—C9—H9	120.3	H15A—C15—H15B	109.5
C10—C9—H9	120.3	O4—C15—H15C	109.5
C12—C11—C10	118.9 (2)	H15A—C15—H15C	109.5
C12—C11—C14	119.9 (3)	H15B—C15—H15C	109.5
O2—S1—O3—C8	−59.07 (17)	S1—O3—C8—C13	−104.3 (2)
O1—S1—O3—C8	172.70 (15)	C2—C1—C6—C5	0.3 (4)
C1—S1—O3—C8	57.18 (17)	S1—C1—C6—C5	−179.55 (18)
O2—S1—C1—C2	−154.40 (19)	C1—C6—C5—C4	0.0 (4)
O1—S1—C1—C2	−20.4 (2)	C13—C8—C9—C10	2.0 (4)
O3—S1—C1—C2	89.5 (2)	O3—C8—C9—C10	179.2 (2)
O2—S1—C1—C6	25.4 (2)	C13—C12—C11—C10	1.0 (4)
O1—S1—C1—C6	159.38 (18)	C13—C12—C11—C14	−179.6 (2)
O3—S1—C1—C6	−90.64 (19)	C6—C1—C2—C3	−0.2 (4)
C15—O4—C13—C12	−9.7 (3)	S1—C1—C2—C3	179.6 (2)
C15—O4—C13—C8	170.7 (2)	C6—C5—C4—C3	−0.4 (4)
O4—C13—C12—C11	−179.3 (2)	C6—C5—C4—C7	179.4 (2)
C8—C13—C12—C11	0.3 (3)	C8—C9—C10—C11	−0.7 (4)
O4—C13—C8—C9	177.8 (2)	C12—C11—C10—C9	−0.8 (4)
C12—C13—C8—C9	−1.8 (3)	C14—C11—C10—C9	179.8 (2)
O4—C13—C8—O3	0.6 (3)	C5—C4—C3—C2	0.4 (4)
C12—C13—C8—O3	−179.08 (18)	C7—C4—C3—C2	−179.3 (3)
S1—O3—C8—C9	78.4 (2)	C1—C2—C3—C4	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···O1i	0.96	2.60	3.327 (4)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯O1i	0.96	2.60	3.327 (4)	133

Symmetry code: (i) .