In the crystal structure of the title compound, C
17H
14O
3S, the dihedral angle between the mean planes of the 4-tolyl and 1-naphthyl rings is 45.05 (4)°. The supramolecular aggregation is completed by the presence of intermolecular C—H

O and C—H

π interactions.
Supporting information
CCDC reference: 269554
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.092
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H12 .. O2 .. 2.99 Ang.
Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
identifier.
tan
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.04 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O2 .. 2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O2 .. 2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O1 .. 2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. O2 .. 2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O3 .. 2.87 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. CG3 .. 2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. CG3 .. 2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. CG2 .. 3.01 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C3 .. O2 .. 3.80 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C2 .. O2 .. 99.00 Deg.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
13 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
0 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
11 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97.
1-naphthyl 4-toluenesulfonate
top
Crystal data top
C17H14O3S | Z = 2 |
Mr = 298.34 | F(000) = 312 |
Triclinic, P1 | Dx = 1.372 Mg m−3 |
Hall symbol: -P 1 | Melting point = 396–397 K |
a = 8.8693 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3982 (10) Å | Cell parameters from 3629 reflections |
c = 9.7112 (10) Å | θ = 2.5–30.0° |
α = 70.446 (4)° | µ = 0.23 mm−1 |
β = 71.335 (4)° | T = 120 K |
γ = 81.831 (8)° | Fragment, tan |
V = 722.12 (14) Å3 | 0.40 × 0.27 × 0.08 mm |
Data collection top
KappaCCD (with an Oxford Cryosystems Cryostream coller) diffractometer | 4173 independent reflections |
Radiation source: fine-focus sealed tube | 3618 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans with κ offsets | θmax = 30.1°, θmin = 3.1° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −12→12 |
Tmin = 0.934, Tmax = 0.982 | k = −13→13 |
12785 measured reflections | l = −13→13 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0371P)2 + 0.2951P] where P = (Fo2 + 2Fc2)/3 |
4173 reflections | (Δ/σ)max < 0.001 |
246 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.43 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 | 0.27616 (3) | 0.69621 (3) | 0.84693 (3) | 0.01878 (8) | |
O1 | 0.44043 (11) | 0.64780 (11) | 0.81136 (11) | 0.0262 (2) | |
O2 | 0.21933 (12) | 0.81989 (10) | 0.74096 (10) | 0.0278 (2) | |
O3 | 0.17074 (10) | 0.55929 (9) | 0.87136 (10) | 0.01995 (18) | |
C1 | 0.21628 (14) | 0.72478 (13) | 1.02625 (13) | 0.0169 (2) | |
C2 | 0.07282 (14) | 0.80386 (13) | 1.06793 (14) | 0.0191 (2) | |
C3 | 0.02221 (15) | 0.82293 (15) | 1.21147 (15) | 0.0226 (2) | |
C4 | 0.11336 (16) | 0.76464 (15) | 1.31332 (14) | 0.0238 (3) | |
C5 | 0.25789 (16) | 0.68812 (15) | 1.26721 (14) | 0.0236 (2) | |
C6 | 0.31085 (15) | 0.66675 (14) | 1.12429 (14) | 0.0207 (2) | |
C7 | 0.0554 (2) | 0.7846 (2) | 1.46938 (19) | 0.0420 (4) | |
C8 | 0.22678 (13) | 0.40893 (13) | 0.92523 (13) | 0.0177 (2) | |
C9 | 0.20123 (15) | 0.33882 (15) | 1.07827 (14) | 0.0219 (2) | |
C10 | 0.24750 (16) | 0.18480 (15) | 1.12931 (15) | 0.0248 (3) | |
C11 | 0.31563 (15) | 0.10623 (14) | 1.02734 (15) | 0.0226 (2) | |
C12 | 0.41305 (15) | 0.09891 (14) | 0.75945 (16) | 0.0241 (3) | |
C13 | 0.43480 (16) | 0.17064 (15) | 0.60671 (16) | 0.0274 (3) | |
C14 | 0.38663 (17) | 0.32404 (16) | 0.55448 (15) | 0.0268 (3) | |
C15 | 0.31966 (15) | 0.40423 (14) | 0.65588 (14) | 0.0214 (2) | |
C16 | 0.29733 (13) | 0.33325 (13) | 0.81436 (13) | 0.0175 (2) | |
C17 | 0.34306 (14) | 0.17783 (13) | 0.86778 (14) | 0.0191 (2) | |
H2 | 0.0069 (19) | 0.8441 (18) | 0.9993 (19) | 0.027 (4)* | |
H3 | −0.077 (2) | 0.8780 (18) | 1.2415 (18) | 0.029 (4)* | |
H5 | 0.326 (2) | 0.6496 (19) | 1.3372 (19) | 0.033 (4)* | |
H6 | 0.4121 (19) | 0.6113 (18) | 1.0922 (18) | 0.028 (4)* | |
H7A | 0.141 (3) | 0.802 (3) | 1.502 (3) | 0.069 (7)* | |
H7B | −0.020 (3) | 0.864 (3) | 1.475 (3) | 0.082 (8)* | |
H7C | 0.011 (3) | 0.694 (3) | 1.540 (3) | 0.082 (8)* | |
H9 | 0.1505 (19) | 0.3958 (19) | 1.1459 (19) | 0.028 (4)* | |
H10 | 0.230 (2) | 0.134 (2) | 1.238 (2) | 0.036 (5)* | |
H11 | 0.345 (2) | 0.001 (2) | 1.060 (2) | 0.034 (4)* | |
H12 | 0.4413 (19) | −0.0079 (19) | 0.7957 (18) | 0.027 (4)* | |
H13 | 0.486 (2) | 0.116 (2) | 0.538 (2) | 0.034 (4)* | |
H14 | 0.401 (2) | 0.376 (2) | 0.446 (2) | 0.038 (5)* | |
H15 | 0.285 (2) | 0.5090 (19) | 0.6218 (19) | 0.032 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.02205 (15) | 0.01889 (14) | 0.01668 (14) | −0.00053 (10) | −0.00477 (10) | −0.00807 (10) |
O1 | 0.0202 (4) | 0.0337 (5) | 0.0263 (5) | −0.0023 (4) | −0.0010 (3) | −0.0162 (4) |
O2 | 0.0438 (6) | 0.0219 (4) | 0.0193 (4) | −0.0003 (4) | −0.0128 (4) | −0.0052 (4) |
O3 | 0.0203 (4) | 0.0186 (4) | 0.0253 (4) | 0.0029 (3) | −0.0097 (3) | −0.0110 (3) |
C1 | 0.0189 (5) | 0.0171 (5) | 0.0164 (5) | −0.0004 (4) | −0.0056 (4) | −0.0071 (4) |
C2 | 0.0183 (5) | 0.0209 (5) | 0.0208 (5) | 0.0010 (4) | −0.0078 (4) | −0.0086 (4) |
C3 | 0.0191 (6) | 0.0262 (6) | 0.0235 (6) | 0.0004 (5) | −0.0043 (4) | −0.0114 (5) |
C4 | 0.0280 (6) | 0.0270 (6) | 0.0182 (6) | −0.0031 (5) | −0.0054 (5) | −0.0096 (5) |
C5 | 0.0277 (6) | 0.0254 (6) | 0.0205 (6) | 0.0007 (5) | −0.0121 (5) | −0.0065 (5) |
C6 | 0.0219 (6) | 0.0199 (5) | 0.0221 (6) | 0.0029 (4) | −0.0094 (4) | −0.0076 (4) |
C7 | 0.0485 (10) | 0.0587 (11) | 0.0228 (7) | 0.0058 (8) | −0.0091 (7) | −0.0224 (8) |
C8 | 0.0154 (5) | 0.0178 (5) | 0.0216 (5) | 0.0008 (4) | −0.0057 (4) | −0.0084 (4) |
C9 | 0.0203 (6) | 0.0263 (6) | 0.0205 (6) | −0.0008 (4) | −0.0044 (4) | −0.0105 (5) |
C10 | 0.0246 (6) | 0.0283 (6) | 0.0193 (6) | −0.0027 (5) | −0.0069 (5) | −0.0032 (5) |
C11 | 0.0201 (6) | 0.0188 (6) | 0.0273 (6) | −0.0010 (4) | −0.0086 (5) | −0.0033 (5) |
C12 | 0.0215 (6) | 0.0190 (6) | 0.0339 (7) | 0.0002 (4) | −0.0062 (5) | −0.0129 (5) |
C13 | 0.0279 (6) | 0.0265 (6) | 0.0307 (7) | −0.0019 (5) | −0.0018 (5) | −0.0186 (6) |
C14 | 0.0322 (7) | 0.0274 (6) | 0.0204 (6) | −0.0058 (5) | −0.0019 (5) | −0.0104 (5) |
C15 | 0.0252 (6) | 0.0189 (5) | 0.0195 (6) | −0.0020 (4) | −0.0046 (4) | −0.0067 (4) |
C16 | 0.0160 (5) | 0.0174 (5) | 0.0199 (5) | −0.0013 (4) | −0.0042 (4) | −0.0073 (4) |
C17 | 0.0154 (5) | 0.0181 (5) | 0.0245 (6) | −0.0012 (4) | −0.0055 (4) | −0.0076 (4) |
Geometric parameters (Å, º) top
S1—O2 | 1.4244 (9) | C8—C9 | 1.3659 (17) |
S1—O1 | 1.4296 (9) | C8—C16 | 1.4183 (16) |
S1—O3 | 1.6068 (9) | C9—C10 | 1.4109 (18) |
S1—C1 | 1.7513 (11) | C9—H9 | 0.948 (17) |
O3—C8 | 1.4105 (14) | C10—C11 | 1.3677 (19) |
C1—C2 | 1.3922 (16) | C10—H10 | 0.970 (18) |
C1—C6 | 1.3932 (16) | C11—C17 | 1.4213 (18) |
C2—C3 | 1.3858 (17) | C11—H11 | 0.960 (17) |
C2—H2 | 0.973 (16) | C12—C13 | 1.370 (2) |
C3—C4 | 1.3983 (18) | C12—C17 | 1.4197 (17) |
C3—H3 | 0.968 (17) | C12—H12 | 0.971 (16) |
C4—C5 | 1.3954 (18) | C13—C14 | 1.4115 (19) |
C4—C7 | 1.5036 (19) | C13—H13 | 0.942 (18) |
C5—C6 | 1.3892 (17) | C14—C15 | 1.3732 (17) |
C5—H5 | 0.998 (17) | C14—H14 | 0.976 (18) |
C6—H6 | 0.986 (16) | C15—C16 | 1.4171 (17) |
C7—H7A | 0.96 (3) | C15—H15 | 0.966 (17) |
C7—H7B | 0.94 (3) | C16—C17 | 1.4235 (16) |
C7—H7C | 0.94 (3) | | |
| | | |
O2—S1—O1 | 120.59 (6) | C9—C8—O3 | 120.41 (10) |
O2—S1—O3 | 103.28 (5) | C9—C8—C16 | 122.80 (11) |
O1—S1—O3 | 108.74 (5) | O3—C8—C16 | 116.58 (10) |
O2—S1—C1 | 109.69 (6) | C8—C9—C10 | 119.05 (11) |
O1—S1—C1 | 109.43 (6) | C8—C9—H9 | 118.1 (10) |
O3—S1—C1 | 103.66 (5) | C10—C9—H9 | 122.8 (10) |
C8—O3—S1 | 119.57 (7) | C11—C10—C9 | 120.58 (12) |
C2—C1—C6 | 121.59 (11) | C11—C10—H10 | 119.6 (11) |
C2—C1—S1 | 118.60 (9) | C9—C10—H10 | 119.9 (11) |
C6—C1—S1 | 119.80 (9) | C10—C11—C17 | 120.96 (11) |
C3—C2—C1 | 118.96 (11) | C10—C11—H11 | 121.6 (10) |
C3—C2—H2 | 119.6 (10) | C17—C11—H11 | 117.4 (10) |
C1—C2—H2 | 121.4 (10) | C13—C12—C17 | 120.62 (12) |
C2—C3—C4 | 120.91 (11) | C13—C12—H12 | 120.4 (9) |
C2—C3—H3 | 119.6 (10) | C17—C12—H12 | 118.9 (10) |
C4—C3—H3 | 119.5 (10) | C12—C13—C14 | 120.52 (12) |
C5—C4—C3 | 118.76 (11) | C12—C13—H13 | 118.2 (11) |
C5—C4—C7 | 121.08 (13) | C14—C13—H13 | 121.2 (11) |
C3—C4—C7 | 120.15 (13) | C15—C14—C13 | 120.45 (12) |
C6—C5—C4 | 121.43 (11) | C15—C14—H14 | 118.6 (11) |
C6—C5—H5 | 119.0 (10) | C13—C14—H14 | 120.9 (11) |
C4—C5—H5 | 119.6 (10) | C14—C15—C16 | 120.20 (12) |
C5—C6—C1 | 118.33 (11) | C14—C15—H15 | 121.3 (10) |
C5—C6—H6 | 121.5 (9) | C16—C15—H15 | 118.5 (10) |
C1—C6—H6 | 120.1 (9) | C15—C16—C8 | 123.02 (11) |
C4—C7—H7A | 112.0 (14) | C15—C16—C17 | 119.52 (11) |
C4—C7—H7B | 112.9 (16) | C8—C16—C17 | 117.44 (11) |
H7A—C7—H7B | 108 (2) | C12—C17—C11 | 122.15 (11) |
C4—C7—H7C | 107.9 (16) | C12—C17—C16 | 118.68 (11) |
H7A—C7—H7C | 106 (2) | C11—C17—C16 | 119.17 (11) |
H7B—C7—H7C | 110 (2) | | |
| | | |
O2—S1—O3—C8 | 158.11 (8) | O3—C8—C9—C10 | 175.02 (10) |
O1—S1—O3—C8 | 28.90 (10) | C16—C8—C9—C10 | 0.42 (18) |
C1—S1—O3—C8 | −87.46 (9) | C8—C9—C10—C11 | −0.60 (19) |
O2—S1—C1—C2 | 31.33 (11) | C9—C10—C11—C17 | 0.68 (19) |
O1—S1—C1—C2 | 165.71 (9) | C17—C12—C13—C14 | −0.6 (2) |
O3—S1—C1—C2 | −78.42 (10) | C12—C13—C14—C15 | 1.1 (2) |
O2—S1—C1—C6 | −149.58 (10) | C13—C14—C15—C16 | −0.4 (2) |
O1—S1—C1—C6 | −15.20 (12) | C14—C15—C16—C8 | −179.03 (12) |
O3—S1—C1—C6 | 100.67 (10) | C14—C15—C16—C17 | −0.75 (18) |
C6—C1—C2—C3 | −1.04 (18) | C9—C8—C16—C15 | 178.02 (12) |
S1—C1—C2—C3 | 178.04 (9) | O3—C8—C16—C15 | 3.22 (16) |
C1—C2—C3—C4 | 0.28 (19) | C9—C8—C16—C17 | −0.30 (17) |
C2—C3—C4—C5 | 0.78 (19) | O3—C8—C16—C17 | −175.10 (10) |
C2—C3—C4—C7 | −179.17 (14) | C13—C12—C17—C11 | 178.66 (12) |
C3—C4—C5—C6 | −1.2 (2) | C13—C12—C17—C16 | −0.57 (18) |
C7—C4—C5—C6 | 178.80 (14) | C10—C11—C17—C12 | −179.79 (12) |
C4—C5—C6—C1 | 0.43 (19) | C10—C11—C17—C16 | −0.56 (18) |
C2—C1—C6—C5 | 0.68 (18) | C15—C16—C17—C12 | 1.23 (17) |
S1—C1—C6—C5 | −178.38 (9) | C8—C16—C17—C12 | 179.61 (10) |
S1—O3—C8—C9 | 84.39 (12) | C15—C16—C17—C11 | −178.02 (11) |
S1—O3—C8—C16 | −100.68 (10) | C8—C16—C17—C11 | 0.35 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2 | 0.973 (16) | 2.670 (16) | 2.9813 (15) | 99.0 (11) |
C6—H6···O1 | 0.986 (16) | 2.565 (16) | 2.9421 (15) | 102.6 (11) |
C15—H15···O3 | 0.966 (17) | 2.487 (17) | 2.8236 (15) | 100.3 (11) |
C3—H3···O2i | 0.968 (17) | 2.975 (17) | 3.7990 (16) | 143.8 (12) |
C6—H6···O1ii | 0.986 (16) | 2.621 (16) | 3.4334 (15) | 139.8 (12) |
C7—H7A···O2iii | 0.96 (3) | 2.69 (3) | 3.515 (2) | 144.1 (18) |
C9—H9···O3iv | 0.948 (17) | 2.870 (16) | 3.2285 (15) | 103.7 (11) |
C12—H12···O2v | 0.971 (16) | 2.988 (16) | 3.4139 (16) | 107.9 (11) |
C14—H14···O1vi | 0.976 (18) | 2.509 (18) | 3.3231 (16) | 140.8 (14) |
C2—H2···Cg2vii | 0.973 (16) | 2.68 | 3.36 | 127 |
C3—H3···Cg3vii | 0.968 (17) | 2.83 | 3.40 | 119 |
C5—H5···Cg3viii | 0.998 (17) | 2.86 | 3.55 | 127 |
C6—H6···Cg2viii | 0.986 (16) | 3.01 | 3.62 | 121 |
C11—H11···Cg1v | 0.960 (17) | 2.78 | 3.49 | 132 |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x+1, −y+1, −z+2; (iii) x, y, z+1; (iv) −x, −y+1, −z+2; (v) x, y−1, z; (vi) −x+1, −y+1, −z+1; (vii) −x, −y+1, −z; (viii) −x+1, −y+1, −z. |