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In the title compound, C
17H
20O
3S, 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.
Supporting information
CCDC reference: 611203
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.79 × 0.56 × 0.45 mm |
Data collection top
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 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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0998P)2] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 0.93 | 2.59 | 3.230 (3) | 126 |
C6—H6···O3ii | 0.93 | 2.59 | 3.478 (4) | 161 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y, −z+1. |
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