4-tert-Butyl­phenyl 4-methyl­benzene­sulfonate

In the title compound, C₁₇H₂₀O₃S, the dihedral angle between the planes of the two aromatic rings is 66.5 (1)°. Weak C—H...O inter­actions are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.182
• Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C14

Author Response: The lower U(eq) value of the atom C14 as compared with the average U(eq) is due to the higher U(eq) value of the Neighbors C14, C15 and C16, this situation often occurs for the t-butyl moiety.

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.49 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.61 Ratio

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.79 mm
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT213_ALERT_2_C Atom C15     has ADP max/min Ratio .............       3.30 prolat
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C16     ..       5.08 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C17     ..       5.66 su

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku 2003); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

4-tert-butylphenyl 4-methylbenzenesulfonate

Crystal data

C17H20O3S	F(000) = 648
Mr = 304.39	Dx = 1.216 Mg m^−3
Monoclinic, P21/c	Melting point = 370–371 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.557 (2) Å	Cell parameters from 11643 reflections
b = 12.611 (3) Å	θ = 1.8–27.5°
c = 11.858 (2) Å	µ = 0.20 mm^−1
β = 105.80 (3)°	T = 293 K
V = 1662.9 (6) Å^3	Block, colourless
Z = 4	0.79 × 0.56 × 0.45 mm

Data collection

Rigaku R-AXIS RAPID imaging-plate diffractometer	3747 independent reflections
Radiation source: Rotating Anode	2344 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.857, Tmax = 0.915	k = −16→16
11643 measured reflections	l = −15→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.182	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0998P)^2] where P = (Fo^2 + 2Fc^2)/3
3747 reflections	(Δ/σ)max = 0.010
191 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.89216 (6)	0.15064 (5)	0.59636 (6)	0.0607 (3)
O1	0.9511 (2)	0.18706 (16)	0.51334 (19)	0.0903 (7)
O2	0.80693 (18)	0.21665 (13)	0.62956 (18)	0.0772 (6)
O3	0.82683 (16)	0.04568 (12)	0.53547 (14)	0.0571 (4)
C1	0.9958 (2)	0.10244 (16)	0.7208 (2)	0.0506 (6)
C2	0.9907 (2)	0.13650 (18)	0.8299 (2)	0.0589 (6)
H2	0.9337	0.1859	0.8378	0.071*
C3	1.0727 (3)	0.0950 (2)	0.9270 (3)	0.0700 (8)
H3	1.0715	0.1187	1.0009	0.084*
C4	1.1562 (2)	0.0200 (2)	0.9185 (3)	0.0672 (7)
C5	1.1596 (2)	−0.0113 (2)	0.8073 (3)	0.0712 (8)
H5	1.2163	−0.0612	0.7996	0.085*
C6	1.0813 (2)	0.0294 (2)	0.7089 (2)	0.0636 (7)
H6	1.0854	0.0084	0.6349	0.076*
C7	1.2427 (3)	−0.0269 (3)	1.0236 (3)	0.0996 (11)
H7A	1.2340	0.0077	1.0930	0.149*
H7B	1.3233	−0.0174	1.0179	0.149*
H7C	1.2264	−0.1013	1.0277	0.149*
C8	0.7620 (2)	−0.01904 (16)	0.59569 (18)	0.0460 (5)
C9	0.6518 (2)	0.01149 (17)	0.6046 (2)	0.0560 (6)
H9	0.6207	0.0776	0.5774	0.067*
C10	0.5866 (2)	−0.05756 (18)	0.6550 (2)	0.0570 (6)
H10	0.5110	−0.0371	0.6605	0.068*
C11	0.6311 (2)	−0.15616 (17)	0.6973 (2)	0.0501 (5)
C12	0.7441 (2)	−0.18281 (18)	0.6865 (2)	0.0604 (7)
H12	0.7766	−0.2484	0.7141	0.072*
C13	0.8098 (2)	−0.11547 (17)	0.6364 (2)	0.0574 (6)
H13	0.8854	−0.1352	0.6304	0.069*
C14	0.5580 (2)	−0.2345 (2)	0.7485 (2)	0.0648 (7)
C15	0.4456 (5)	−0.1855 (4)	0.7666 (7)	0.206 (4)
H15A	0.4029	−0.2375	0.7987	0.309*
H15B	0.3954	−0.1610	0.6928	0.309*
H15C	0.4669	−0.1268	0.8197	0.309*
C16	0.5216 (5)	−0.3259 (4)	0.6638 (4)	0.163 (2)
H16A	0.4755	−0.3760	0.6945	0.244*
H16B	0.5923	−0.3599	0.6534	0.244*
H16C	0.4738	−0.2997	0.5897	0.244*
C17	0.6327 (4)	−0.2793 (4)	0.8633 (3)	0.1259 (15)
H17A	0.5850	−0.3282	0.8937	0.189*
H17B	0.6594	−0.2227	0.9183	0.189*
H17C	0.7012	−0.3156	0.8509	0.189*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0737 (5)	0.0426 (3)	0.0695 (5)	−0.0051 (3)	0.0262 (3)	0.0087 (3)
O1	0.1145 (17)	0.0800 (13)	0.0857 (15)	−0.0239 (12)	0.0428 (13)	0.0264 (11)
O2	0.0849 (13)	0.0451 (8)	0.0997 (15)	0.0108 (9)	0.0221 (12)	−0.0010 (9)
O3	0.0713 (10)	0.0542 (9)	0.0507 (10)	−0.0078 (8)	0.0248 (8)	0.0009 (7)
C1	0.0551 (13)	0.0396 (10)	0.0622 (15)	−0.0051 (10)	0.0248 (11)	−0.0011 (10)
C2	0.0688 (16)	0.0463 (12)	0.0668 (17)	0.0018 (11)	0.0274 (13)	−0.0090 (11)
C3	0.0843 (19)	0.0604 (15)	0.0668 (17)	−0.0033 (15)	0.0231 (15)	−0.0139 (13)
C4	0.0683 (16)	0.0528 (13)	0.0733 (18)	−0.0066 (13)	0.0073 (14)	−0.0066 (12)
C5	0.0596 (15)	0.0591 (14)	0.095 (2)	0.0083 (13)	0.0208 (15)	−0.0095 (15)
C6	0.0645 (15)	0.0619 (14)	0.0715 (17)	0.0008 (13)	0.0308 (14)	−0.0140 (13)
C7	0.098 (2)	0.085 (2)	0.096 (2)	0.004 (2)	−0.009 (2)	0.0054 (19)
C8	0.0533 (12)	0.0427 (10)	0.0427 (12)	−0.0043 (10)	0.0140 (10)	−0.0015 (9)
C9	0.0608 (14)	0.0445 (11)	0.0620 (15)	0.0080 (11)	0.0157 (12)	0.0077 (11)
C10	0.0479 (13)	0.0582 (13)	0.0665 (16)	0.0053 (11)	0.0184 (12)	0.0035 (12)
C11	0.0500 (13)	0.0489 (11)	0.0504 (13)	−0.0022 (10)	0.0120 (10)	0.0010 (10)
C12	0.0587 (14)	0.0425 (11)	0.0805 (18)	0.0048 (11)	0.0199 (13)	0.0138 (12)
C13	0.0501 (13)	0.0473 (12)	0.0798 (17)	0.0053 (11)	0.0261 (12)	0.0040 (12)
C14	0.0633 (15)	0.0612 (14)	0.0710 (17)	−0.0116 (13)	0.0202 (13)	0.0113 (13)
C15	0.148 (4)	0.158 (4)	0.385 (10)	0.049 (4)	0.194 (6)	0.132 (6)
C16	0.225 (6)	0.149 (4)	0.119 (4)	−0.134 (4)	0.054 (4)	−0.022 (3)
C17	0.120 (3)	0.157 (3)	0.097 (3)	−0.039 (3)	0.023 (2)	0.054 (3)

Geometric parameters (Å, º)

S1—O1	1.418 (2)	C9—C10	1.389 (3)
S1—O2	1.4246 (19)	C9—H9	0.93
S1—O3	1.5958 (17)	C10—C11	1.386 (3)
S1—C1	1.737 (3)	C10—H10	0.93
O3—C8	1.424 (2)	C11—C12	1.388 (3)
C1—C2	1.380 (3)	C11—C14	1.528 (3)
C1—C6	1.386 (3)	C12—C13	1.377 (3)
C2—C3	1.379 (4)	C12—H12	0.93
C2—H2	0.93	C13—H13	0.93
C3—C4	1.375 (4)	C14—C15	1.506 (5)
C3—H3	0.93	C14—C17	1.510 (4)
C4—C5	1.386 (4)	C14—C16	1.511 (5)
C4—C7	1.492 (4)	C15—H15A	0.96
C5—C6	1.368 (4)	C15—H15B	0.96
C5—H5	0.93	C15—H15C	0.96
C6—H6	0.93	C16—H16A	0.96
C7—H7A	0.96	C16—H16B	0.96
C7—H7B	0.96	C16—H16C	0.96
C7—H7C	0.96	C17—H17A	0.96
C8—C9	1.362 (3)	C17—H17B	0.96
C8—C13	1.368 (3)	C17—H17C	0.96
O1—S1—O2	120.12 (13)	C11—C10—C9	121.8 (2)
O1—S1—O3	102.26 (12)	C11—C10—H10	119.1
O2—S1—O3	109.40 (10)	C9—C10—H10	119.1
O1—S1—C1	110.64 (13)	C10—C11—C12	116.7 (2)
O2—S1—C1	109.78 (12)	C10—C11—C14	122.2 (2)
O3—S1—C1	103.05 (10)	C12—C11—C14	121.0 (2)
C8—O3—S1	119.81 (13)	C13—C12—C11	122.2 (2)
C2—C1—C6	121.1 (2)	C13—C12—H12	118.9
C2—C1—S1	119.47 (19)	C11—C12—H12	118.9
C6—C1—S1	119.47 (19)	C8—C13—C12	118.9 (2)
C1—C2—C3	118.0 (2)	C8—C13—H13	120.5
C1—C2—H2	121.0	C12—C13—H13	120.5
C3—C2—H2	121.0	C15—C14—C17	109.2 (4)
C4—C3—C2	122.4 (3)	C15—C14—C16	108.2 (4)
C4—C3—H3	118.8	C17—C14—C16	107.5 (3)
C2—C3—H3	118.8	C15—C14—C11	112.5 (2)
C3—C4—C5	117.9 (3)	C17—C14—C11	111.0 (2)
C3—C4—C7	122.4 (3)	C16—C14—C11	108.3 (2)
C5—C4—C7	119.7 (3)	C14—C15—H15A	109.5
C6—C5—C4	121.4 (2)	C14—C15—H15B	109.5
C6—C5—H5	119.3	H15A—C15—H15B	109.5
C4—C5—H5	119.3	C14—C15—H15C	109.5
C5—C6—C1	119.1 (2)	H15A—C15—H15C	109.5
C5—C6—H6	120.4	H15B—C15—H15C	109.5
C1—C6—H6	120.4	C14—C16—H16A	109.5
C4—C7—H7A	109.5	C14—C16—H16B	109.5
C4—C7—H7B	109.5	H16A—C16—H16B	109.5
H7A—C7—H7B	109.5	C14—C16—H16C	109.5
C4—C7—H7C	109.5	H16A—C16—H16C	109.5
H7A—C7—H7C	109.5	H16B—C16—H16C	109.5
H7B—C7—H7C	109.5	C14—C17—H17A	109.5
C9—C8—C13	121.3 (2)	C14—C17—H17B	109.5
C9—C8—O3	120.51 (19)	H17A—C17—H17B	109.5
C13—C8—O3	118.0 (2)	C14—C17—H17C	109.5
C8—C9—C10	119.0 (2)	H17A—C17—H17C	109.5
C8—C9—H9	120.5	H17B—C17—H17C	109.5
C10—C9—H9	120.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.53	2.903 (3)	104
C2—H2···O1^i	0.93	2.59	3.230 (3)	126
C6—H6···O3^ii	0.93	2.59	3.478 (4)	161

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