In the crystal structure of the title compound, C
13H
12O
3S, the dihedral angle between the mean planes of the 4-tolyl and phenyl rings is 52.6 (1)°. There are weak C—H
O hydrogen bonds, which generate rings of graph-set motifs
R12(4) and
R21(9). The supramolecular aggregation is completed by the presence of van der Waals short contacts and C—H
π interactions.
Supporting information
CCDC reference: 269552
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- R factor = 0.067
- wR factor = 0.177
- Data-to-parameter ratio = 20.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H2 .. O2 .. 2.99 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H7B .. O2 .. 2.98 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H11 .. CG1 .. 3.33 Ang.
Alert level C
DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75
_refine_diff_density_min given = -1.402
Test value = -1.200
DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -1.40 e/A 3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O2 .. 2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O1 .. 2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O1 .. 2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. O1 .. 2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O3 .. 2.78 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O2 .. 2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. O3 .. 2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. CG2 .. 2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. CG2 .. 3.08 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C2 .. O2 .. 3.76 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C11 .. CG1 .. 4.09 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C2 .. O2 .. 99.00 Deg.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C9 .. O1 .. 95.00 Deg.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 30.04
From the CIF: _reflns_number_total 3277
Count of symmetry unique reflns 1891
Completeness (_total/calc) 173.29%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1386
Fraction of Friedel pairs measured 0.733
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
17 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
17 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Phenyl 4-toluenesulfonate
top
Crystal data top
C13H12O3S | Dx = 1.390 Mg m−3 |
Mr = 248.29 | Melting point = 367–368 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2c -2ac | Cell parameters from 25 reflections |
a = 25.149 (4) Å | θ = 15–19° |
b = 7.976 (5) Å | µ = 0.27 mm−1 |
c = 5.916 (4) Å | T = 173 K |
V = 1186.7 (10) Å3 | Plate, colorless |
Z = 4 | 0.50 × 0.33 × 0.15 mm |
F(000) = 520 | |
Data collection top
Rigaku AFC-5R diffractometer | 2819 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 30.0°, θmin = 2.6° |
ω scans | h = −35→35 |
Absorption correction: ψ scan (North et al., 1968) | k = −11→10 |
Tmin = 0.946, Tmax = 0.963 | l = −8→8 |
3909 measured reflections | 3 standard reflections every 150 reflections |
3277 independent reflections | intensity decay: none |
Refinement top
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)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.177 | w = 1/[σ2(Fo2) + (0.1163P)2 + 0.1087P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
3277 reflections | Δρmax = 0.60 e Å−3 |
157 parameters | Δρmin = −1.40 e Å−3 |
1 restraint | Absolute structure: (Flack, 1983), 1386 Friedel pairs? |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.07 (12) |
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 | 0.34695 (2) | 0.69543 (8) | 0.44852 (13) | 0.02728 (19) | |
O1 | 0.36778 (11) | 0.7369 (3) | 0.2305 (4) | 0.0381 (5) | |
O2 | 0.30335 (9) | 0.5822 (3) | 0.4718 (5) | 0.0418 (6) | |
O3 | 0.39332 (8) | 0.6063 (2) | 0.5929 (4) | 0.0287 (4) | |
C1 | 0.33453 (10) | 0.8811 (4) | 0.5984 (5) | 0.0237 (5) | |
C2 | 0.30789 (11) | 0.8722 (4) | 0.8058 (5) | 0.0268 (5) | |
H2 | 0.2964 | 0.7699 | 0.8632 | 0.055 (4)* | |
C3 | 0.29905 (11) | 1.0202 (4) | 0.9237 (5) | 0.0293 (6) | |
H3 | 0.2813 | 1.0159 | 1.0614 | 0.055 (4)* | |
C4 | 0.31605 (12) | 1.1749 (4) | 0.8415 (5) | 0.0285 (6) | |
C5 | 0.34174 (12) | 1.1797 (4) | 0.6319 (6) | 0.0308 (6) | |
H5 | 0.3526 | 1.2821 | 0.5725 | 0.055 (4)* | |
C6 | 0.35127 (12) | 1.0336 (4) | 0.5115 (5) | 0.0290 (6) | |
H6 | 0.3688 | 1.0379 | 0.3732 | 0.055 (4)* | |
C7 | 0.30695 (14) | 1.3344 (5) | 0.9751 (7) | 0.0412 (8) | |
H7A | 0.3371 | 1.4071 | 0.9581 | 0.083 (11)* | |
H7B | 0.3023 | 1.3072 | 1.1319 | 0.083 (11)* | |
H7C | 0.2757 | 1.3898 | 0.9199 | 0.083 (11)* | |
C8 | 0.44463 (11) | 0.6773 (4) | 0.5835 (5) | 0.0268 (5) | |
C9 | 0.47793 (12) | 0.6383 (4) | 0.4047 (5) | 0.0318 (6) | |
H9 | 0.4662 | 0.5698 | 0.2876 | 0.055 (4)* | |
C10 | 0.52921 (13) | 0.7034 (4) | 0.4036 (5) | 0.0371 (7) | |
H10 | 0.5521 | 0.6782 | 0.2850 | 0.055 (4)* | |
C11 | 0.54647 (13) | 0.8061 (5) | 0.5794 (7) | 0.0400 (8) | |
H11 | 0.5807 | 0.8503 | 0.5770 | 0.055 (4)* | |
C12 | 0.51273 (13) | 0.8425 (5) | 0.7578 (6) | 0.0394 (7) | |
H12 | 0.5244 | 0.9110 | 0.8749 | 0.055 (4)* | |
C13 | 0.46117 (13) | 0.7769 (4) | 0.7629 (5) | 0.0335 (7) | |
H13 | 0.4385 | 0.7994 | 0.8833 | 0.055 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0307 (3) | 0.0287 (3) | 0.0224 (3) | 0.0025 (2) | −0.0044 (3) | −0.0034 (3) |
O1 | 0.0505 (13) | 0.0461 (13) | 0.0177 (8) | 0.0077 (11) | −0.0009 (9) | −0.0034 (10) |
O2 | 0.0379 (10) | 0.0380 (12) | 0.0494 (15) | −0.0036 (9) | −0.0088 (11) | −0.0114 (12) |
O3 | 0.0305 (9) | 0.0282 (10) | 0.0272 (9) | 0.0022 (7) | −0.0014 (8) | 0.0034 (8) |
C1 | 0.0238 (10) | 0.0289 (13) | 0.0183 (10) | 0.0032 (9) | −0.0010 (9) | 0.0002 (10) |
C2 | 0.0309 (12) | 0.0304 (14) | 0.0190 (11) | 0.0002 (10) | −0.0005 (10) | 0.0065 (11) |
C3 | 0.0307 (11) | 0.0389 (15) | 0.0183 (11) | 0.0019 (10) | 0.0012 (10) | 0.0019 (12) |
C4 | 0.0289 (12) | 0.0326 (14) | 0.0240 (12) | 0.0031 (11) | −0.0027 (10) | −0.0017 (11) |
C5 | 0.0362 (14) | 0.0294 (14) | 0.0267 (15) | −0.0051 (11) | 0.0024 (11) | 0.0013 (12) |
C6 | 0.0332 (12) | 0.0319 (15) | 0.0219 (11) | −0.0022 (11) | 0.0031 (9) | −0.0004 (10) |
C7 | 0.0463 (16) | 0.0402 (17) | 0.0372 (18) | 0.0077 (13) | −0.0025 (15) | −0.0108 (16) |
C8 | 0.0294 (12) | 0.0282 (13) | 0.0227 (11) | 0.0014 (9) | −0.0016 (10) | 0.0019 (11) |
C9 | 0.0350 (14) | 0.0367 (15) | 0.0238 (13) | 0.0034 (12) | −0.0020 (11) | −0.0077 (12) |
C10 | 0.0353 (14) | 0.0484 (18) | 0.0276 (16) | 0.0036 (12) | 0.0051 (12) | −0.0081 (14) |
C11 | 0.0321 (14) | 0.055 (2) | 0.0330 (15) | −0.0025 (13) | −0.0011 (14) | −0.0089 (15) |
C12 | 0.0363 (15) | 0.052 (2) | 0.0298 (15) | −0.0009 (14) | −0.0044 (13) | −0.0141 (15) |
C13 | 0.0364 (14) | 0.0451 (18) | 0.0189 (12) | 0.0045 (13) | −0.0014 (10) | −0.0048 (12) |
Geometric parameters (Å, º) top
S1—O2 | 1.427 (2) | C6—H6 | 0.9300 |
S1—O1 | 1.431 (3) | C7—H7A | 0.9600 |
S1—O3 | 1.611 (2) | C7—H7B | 0.9600 |
S1—C1 | 1.754 (3) | C7—H7C | 0.9600 |
O3—C8 | 1.410 (3) | C8—C9 | 1.384 (4) |
C1—C6 | 1.386 (4) | C8—C13 | 1.390 (4) |
C1—C2 | 1.400 (4) | C9—C10 | 1.390 (4) |
C2—C3 | 1.388 (4) | C9—H9 | 0.9300 |
C2—H2 | 0.9300 | C10—C11 | 1.394 (5) |
C3—C4 | 1.394 (4) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—C12 | 1.385 (5) |
C4—C5 | 1.399 (4) | C11—H11 | 0.9300 |
C4—C7 | 1.515 (4) | C12—C13 | 1.398 (5) |
C5—C6 | 1.387 (4) | C12—H12 | 0.9300 |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
| | | |
O2—S1—O1 | 120.98 (17) | C4—C7—H7A | 109.5 |
O2—S1—O3 | 103.05 (13) | C4—C7—H7B | 109.5 |
O1—S1—O3 | 108.36 (14) | H7A—C7—H7B | 109.5 |
O2—S1—C1 | 110.40 (14) | C4—C7—H7C | 109.5 |
O1—S1—C1 | 108.99 (14) | H7A—C7—H7C | 109.5 |
O3—S1—C1 | 103.50 (13) | H7B—C7—H7C | 109.5 |
C8—O3—S1 | 117.68 (18) | C9—C8—C13 | 122.1 (3) |
C6—C1—C2 | 121.0 (3) | C9—C8—O3 | 119.6 (3) |
C6—C1—S1 | 120.0 (2) | C13—C8—O3 | 118.2 (3) |
C2—C1—S1 | 119.1 (2) | C8—C9—C10 | 118.7 (3) |
C3—C2—C1 | 118.3 (3) | C8—C9—H9 | 120.6 |
C3—C2—H2 | 120.9 | C10—C9—H9 | 120.6 |
C1—C2—H2 | 120.9 | C9—C10—C11 | 120.3 (3) |
C2—C3—C4 | 121.9 (3) | C9—C10—H10 | 119.8 |
C2—C3—H3 | 119.1 | C11—C10—H10 | 119.8 |
C4—C3—H3 | 119.1 | C12—C11—C10 | 120.1 (3) |
C3—C4—C5 | 118.3 (3) | C12—C11—H11 | 120.0 |
C3—C4—C7 | 121.0 (3) | C10—C11—H11 | 120.0 |
C5—C4—C7 | 120.6 (3) | C11—C12—C13 | 120.4 (3) |
C6—C5—C4 | 120.8 (3) | C11—C12—H12 | 119.8 |
C6—C5—H5 | 119.6 | C13—C12—H12 | 119.8 |
C4—C5—H5 | 119.6 | C8—C13—C12 | 118.4 (3) |
C1—C6—C5 | 119.6 (3) | C8—C13—H13 | 120.8 |
C1—C6—H6 | 120.2 | C12—C13—H13 | 120.8 |
C5—C6—H6 | 120.2 | | |
| | | |
O2—S1—O3—C8 | 172.8 (2) | C7—C4—C5—C6 | 178.5 (3) |
O1—S1—O3—C8 | 43.5 (3) | C2—C1—C6—C5 | 0.3 (4) |
C1—S1—O3—C8 | −72.1 (2) | S1—C1—C6—C5 | −179.4 (2) |
O2—S1—C1—C6 | −143.2 (2) | C4—C5—C6—C1 | 0.9 (4) |
O1—S1—C1—C6 | −8.1 (3) | S1—O3—C8—C9 | −82.7 (3) |
O3—S1—C1—C6 | 107.1 (2) | S1—O3—C8—C13 | 101.1 (3) |
O2—S1—C1—C2 | 37.1 (3) | C13—C8—C9—C10 | −1.1 (5) |
O1—S1—C1—C2 | 172.2 (2) | O3—C8—C9—C10 | −177.1 (3) |
O3—S1—C1—C2 | −72.6 (2) | C8—C9—C10—C11 | −0.1 (5) |
C6—C1—C2—C3 | −0.6 (4) | C9—C10—C11—C12 | 0.7 (6) |
S1—C1—C2—C3 | 179.1 (2) | C10—C11—C12—C13 | −0.1 (6) |
C1—C2—C3—C4 | −0.2 (4) | C9—C8—C13—C12 | 1.6 (5) |
C2—C3—C4—C5 | 1.3 (4) | O3—C8—C13—C12 | 177.7 (3) |
C2—C3—C4—C7 | −178.8 (3) | C11—C12—C13—C8 | −1.0 (5) |
C3—C4—C5—C6 | −1.6 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2 | 0.93 | 2.76 | 3.044 (4) | 99 |
C6—H6···O1 | 0.93 | 2.54 | 2.921 (4) | 105 |
C9—H9···O1 | 0.93 | 2.83 | 3.058 (4) | 95 |
C2—H2···O1i | 0.93 | 2.83 | 3.122 (4) | 100 |
C13—H13···O1i | 0.93 | 2.76 | 3.643 (4) | 158 |
C2—H2···O2ii | 0.93 | 2.99 | 3.761 (4) | 141 |
C5—H5···O3iii | 0.93 | 2.78 | 3.649 (4) | 155 |
C5—H5···O2iii | 0.93 | 2.76 | 3.484 (4) | 135 |
C7—H7B···O2iv | 0.96 | 2.98 | 3.543 (5) | 119 |
C7—H7C···O2v | 0.96 | 2.53 | 3.406 (4) | 152 |
C10—H10···O3vi | 0.93 | 2.89 | 3.644 (4) | 140 |
C3—H3···Cg1ii | 0.93 | 2.83 | 3.577 | 138 |
C9—H9···Cg2vii | 0.93 | 2.92 | 3.638 | 135 |
C11—H11···Cg1viii | 0.93 | 3.33 | 4.094 | 141 |
C12—H12···Cg2ix | 0.93 | 3.08 | 3.843 | 141 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1/2, y, z+1/2; (iii) x, y+1, z; (iv) x, y+1, z+1; (v) −x+1/2, y+1, z+1/2; (vi) −x+1, −y+1, z−1/2; (vii) −x, −y+1, z−1/2; (viii) −x, −y+2, z−1/2; (ix) −x, −y+2, z+1/2. |