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In bis(4-tolyl) sulfone, C14H14O2S (1), 2,5,4′-trimethyldiphenyl sulfone, C15H16O2S (2), and 4-chlorodiphenyl sulfone, C12H9ClO2S (3), the molecules are linked by soft C—H...O hydrogen bonds into three different types of one-dimensional aggregate: simple chains in (1), molecular ladders in (2) and chains of fused rings in (3). In each of 3,4-dimethyl-4′-chlorodiphenyl sulfone, C14H13ClO2S (4), and 2,5-dimethyldiphenyl sulfone, C14H14O2S (5), the C—H...O hydrogen bonds link the molecules into two different types of two-dimensional sheet, based on a (4,4) net in (4) and a (3,6) net in (5). The patterns of soft C—H...O hydrogen bonds in (1)—(5) are compared with those in other diaryl sulfones, mainly retrieved from the Cambridge Structural Database, whose substitution patterns preclude the formation of hard hydrogen bonds. Observed aggregation modes range from the formation of no C—H...O hydrogen bonds at all, via finite (zero-dimensional) arrays through one-, two- and three-dimensional systems.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100015494/bm0036sup1.cif
Contains datablocks global, 1, 2, 3, 4, 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100015494/bm00361sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100015494/bm00362sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100015494/bm00363sup4.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100015494/bm00364sup5.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100015494/bm00365sup6.hkl
Contains datablock 5

CCDC references: 163039; 163040; 163041; 163042; 163043

Comment top

In full text version

Experimental top

In full text version

Refinement top

In full text version

Computing details top

Data collection: SMART (Bruker, 1997) for (1), (3); Kappa-CCD server software (Nonius, 1997) for (2), (4), (5). Cell refinement: SAINT (Bruker, 1997) for (1), (3); DENZO (Otwinowski & Minor, 1997) for (2), (4), (5). Data reduction: SAINT (Bruker, 1997) for (1), (3); DENZO (Otwinowski & Minor, 1997) for (2), (4), (5). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b). Molecular graphics: PLATON (Spek, 2000) for (1), (3); ORTEP (Johnson, 1976), PLATON (Spek, 2000) for (2), (4), (5). For all compounds, software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

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In full text version
(1) Bis-(4-tolyl) sulfone top
Crystal data top
C14H14O2SF(000) = 1040
Mr = 246.31Dx = 1.265 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.1773 (7) ÅCell parameters from 15872 reflections
b = 7.7437 (4) Åθ = 1.5–25.0°
c = 24.0161 (12) ŵ = 0.24 mm1
β = 101.205 (1)°T = 306 K
V = 2586.3 (2) Å3Needle, colourless
Z = 80.56 × 0.18 × 0.13 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
4554 independent reflections
Radiation source: fine-focus sealed X-ray tube2746 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ϕ scans and ω scans with κ offsetsθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
SADABS (Bruker, 1997)
h = 1616
Tmin = 0.879, Tmax = 0.970k = 99
15872 measured reflectionsl = 2822
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0511P)2]
where P = (Fo2 + 2Fc2)/3
4554 reflections(Δ/σ)max < 0.001
311 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C14H14O2SV = 2586.3 (2) Å3
Mr = 246.31Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.1773 (7) ŵ = 0.24 mm1
b = 7.7437 (4) ÅT = 306 K
c = 24.0161 (12) Å0.56 × 0.18 × 0.13 mm
β = 101.205 (1)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
4554 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 1997)
2746 reflections with I > 2σ(I)
Tmin = 0.879, Tmax = 0.970Rint = 0.023
15872 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 0.93Δρmax = 0.14 e Å3
4554 reflectionsΔρmin = 0.23 e Å3
311 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1A0.24013 (4)0.87124 (8)0.34337 (2)0.0686 (2)
O1A0.25425 (12)0.9434 (2)0.39953 (6)0.0899 (5)
O2A0.18549 (12)0.7149 (2)0.33154 (7)0.0961 (6)
C1A0.35449 (15)0.8367 (2)0.32655 (8)0.0560 (5)
C2A0.36334 (17)0.7421 (3)0.27882 (9)0.0700 (6)
C3A0.45260 (19)0.7146 (3)0.26651 (10)0.0771 (7)
C4A0.53513 (18)0.7763 (3)0.30085 (11)0.0721 (6)
C5A0.52521 (17)0.8694 (3)0.34834 (10)0.0753 (6)
C6A0.43592 (17)0.9014 (3)0.36107 (9)0.0680 (6)
C7A0.63242 (19)0.7456 (4)0.28665 (13)0.1132 (10)
C11A0.18541 (14)1.0286 (3)0.29492 (8)0.0570 (5)
C12A0.13688 (16)0.9823 (3)0.24176 (10)0.0751 (6)
C13A0.09612 (17)1.1078 (4)0.20416 (10)0.0857 (7)
C14A0.10220 (16)1.2799 (4)0.21773 (12)0.0777 (7)
C15A0.14976 (18)1.3238 (3)0.27114 (13)0.0844 (7)
C16A0.19170 (16)1.2002 (3)0.30968 (10)0.0723 (6)
C17A0.06006 (19)1.4165 (4)0.17519 (12)0.1185 (11)
S1B0.74507 (4)0.23084 (8)0.41418 (3)0.0735 (2)
O1B0.74717 (12)0.2700 (3)0.35586 (7)0.1049 (6)
O2B0.77506 (12)0.0630 (2)0.43635 (8)0.1018 (6)
C1B0.81210 (14)0.3885 (3)0.45778 (9)0.0593 (5)
C2B0.84830 (15)0.3531 (3)0.51413 (9)0.0684 (6)
C3B0.89424 (16)0.4822 (4)0.54840 (10)0.0797 (7)
C4B0.90558 (16)0.6456 (4)0.52858 (12)0.0770 (7)
C5B0.86955 (17)0.6772 (3)0.47183 (13)0.0852 (8)
C6B0.82273 (16)0.5516 (3)0.43639 (10)0.0754 (7)
C7B0.95345 (18)0.7873 (4)0.56691 (13)0.1202 (11)
C11B0.62691 (15)0.2657 (2)0.42496 (9)0.0571 (5)
C12B0.59972 (16)0.1994 (3)0.47255 (9)0.0671 (6)
C13B0.50825 (18)0.2346 (3)0.48208 (10)0.0746 (7)
C14B0.44386 (16)0.3347 (3)0.44516 (11)0.0702 (6)
C15B0.47337 (18)0.3979 (3)0.39775 (11)0.0787 (7)
C16B0.56384 (17)0.3651 (3)0.38758 (9)0.0717 (6)
C17B0.34563 (17)0.3725 (4)0.45697 (12)0.1095 (10)
H2A0.30890.69750.25520.084*
H3A0.45760.65260.23410.093*
H5A0.57980.91150.37230.090*
H6A0.43080.96650.39290.082*
H7A0.68040.80480.31360.170*0.50
H7B0.63300.78850.24920.170*0.50
H7C0.64600.62410.28800.170*0.50
H7D0.62580.67340.25360.170*0.50
H7E0.67330.68980.31800.170*0.50
H7F0.66030.85410.27920.170*0.50
H12A0.13160.86650.23130.090*
H13A0.06341.07490.16840.103*
H15A0.15391.43950.28170.101*
H16A0.22411.23320.34550.087*
H17A0.00611.39000.16020.178*0.50
H17B0.09521.41920.14480.178*0.50
H17C0.06441.52720.19350.178*0.50
H17D0.10841.50090.17220.178*0.50
H17E0.00711.47170.18750.178*0.50
H17F0.03791.36370.13880.178*0.50
H2B0.84180.24350.52880.082*
H3B0.91850.45790.58640.096*
H5B0.87720.78640.45720.102*
H6B0.79850.57610.39840.090*
H7G0.92160.89500.55600.180*0.50
H7H1.01970.79590.56370.180*0.50
H7I0.94950.76140.60550.180*0.50
H7J1.00560.73990.59410.180*0.50
H7K0.90750.83900.58640.180*0.50
H7L0.97780.87340.54460.180*0.50
H12B0.64210.13180.49800.081*
H13B0.48980.18960.51420.090*
H15B0.43110.46450.37200.094*
H16B0.58230.41020.35540.086*
H17G0.30890.43550.42570.164*0.50
H17H0.35170.44030.49090.164*0.50
H17I0.31360.26600.46180.164*0.50
H17J0.34060.32570.49330.164*0.50
H17K0.29770.32090.42800.164*0.50
H17L0.33590.49520.45710.164*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0796 (4)0.0687 (4)0.0612 (4)0.0042 (3)0.0231 (3)0.0082 (3)
O1A0.1112 (13)0.1143 (13)0.0496 (9)0.0255 (11)0.0289 (9)0.0043 (9)
O2A0.1017 (13)0.0698 (11)0.1225 (15)0.0168 (10)0.0358 (11)0.0152 (10)
C1A0.0739 (14)0.0501 (12)0.0435 (12)0.0042 (11)0.0102 (10)0.0013 (9)
C2A0.0789 (16)0.0730 (16)0.0551 (14)0.0049 (13)0.0058 (12)0.0085 (11)
C3A0.100 (2)0.0760 (16)0.0593 (15)0.0166 (15)0.0241 (14)0.0057 (12)
C4A0.0794 (17)0.0625 (15)0.0788 (17)0.0122 (13)0.0262 (14)0.0137 (13)
C5A0.0709 (16)0.0708 (15)0.0810 (18)0.0044 (13)0.0067 (13)0.0015 (13)
C6A0.0862 (17)0.0636 (14)0.0528 (13)0.0035 (13)0.0097 (12)0.0083 (11)
C7A0.098 (2)0.112 (2)0.142 (3)0.0247 (18)0.0543 (19)0.0253 (19)
C11A0.0580 (13)0.0613 (14)0.0536 (13)0.0005 (11)0.0159 (10)0.0014 (10)
C12A0.0772 (16)0.0735 (16)0.0714 (16)0.0032 (13)0.0068 (13)0.0075 (13)
C13A0.0736 (17)0.113 (2)0.0645 (16)0.0035 (16)0.0008 (12)0.0030 (16)
C14A0.0589 (15)0.096 (2)0.0832 (19)0.0120 (15)0.0252 (13)0.0206 (16)
C15A0.0910 (19)0.0606 (15)0.106 (2)0.0091 (14)0.0297 (16)0.0032 (15)
C16A0.0803 (16)0.0708 (16)0.0649 (15)0.0017 (14)0.0117 (12)0.0064 (13)
C17A0.097 (2)0.136 (2)0.128 (2)0.0353 (19)0.0335 (18)0.063 (2)
S1B0.0729 (4)0.0802 (4)0.0698 (4)0.0102 (3)0.0202 (3)0.0138 (3)
O1B0.1013 (13)0.1600 (17)0.0595 (11)0.0036 (12)0.0309 (9)0.0240 (11)
O2B0.0973 (13)0.0651 (11)0.1415 (16)0.0257 (10)0.0194 (11)0.0157 (10)
C1B0.0535 (12)0.0682 (14)0.0586 (14)0.0127 (11)0.0169 (10)0.0013 (11)
C2B0.0614 (14)0.0751 (16)0.0678 (16)0.0090 (12)0.0103 (12)0.0079 (13)
C3B0.0613 (15)0.111 (2)0.0651 (16)0.0083 (15)0.0084 (12)0.0030 (16)
C4B0.0513 (14)0.092 (2)0.092 (2)0.0059 (14)0.0238 (13)0.0174 (16)
C5B0.0775 (17)0.0658 (16)0.119 (2)0.0028 (14)0.0361 (17)0.0027 (16)
C6B0.0769 (16)0.0823 (18)0.0692 (16)0.0080 (14)0.0193 (13)0.0114 (14)
C7B0.0811 (19)0.129 (2)0.155 (3)0.0177 (19)0.0337 (18)0.068 (2)
C11B0.0636 (13)0.0544 (12)0.0522 (13)0.0016 (11)0.0090 (10)0.0070 (10)
C12B0.0705 (15)0.0704 (14)0.0578 (14)0.0034 (12)0.0058 (12)0.0027 (11)
C13B0.0785 (16)0.0890 (17)0.0587 (15)0.0159 (15)0.0193 (13)0.0084 (13)
C14B0.0617 (15)0.0698 (15)0.0782 (17)0.0034 (13)0.0110 (13)0.0303 (13)
C15B0.0767 (17)0.0705 (16)0.0834 (18)0.0169 (13)0.0024 (14)0.0009 (14)
C16B0.0790 (17)0.0712 (15)0.0651 (15)0.0076 (13)0.0145 (13)0.0099 (12)
C17B0.0718 (17)0.126 (2)0.134 (3)0.0052 (16)0.0285 (16)0.060 (2)
Geometric parameters (Å, º) top
S1A—O2A1.4357 (16)S1B—O2B1.4372 (16)
S1A—O1A1.4378 (15)S1B—O1B1.4392 (17)
S1A—C11A1.758 (2)S1B—C1B1.761 (2)
S1A—C1A1.766 (2)S1B—C11B1.765 (2)
C1A—C6A1.378 (3)C1B—C2B1.378 (3)
C1A—C2A1.387 (3)C1B—C6B1.383 (3)
C2A—C3A1.371 (3)C2B—C3B1.376 (3)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.379 (3)C3B—C4B1.372 (3)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.379 (3)C4B—C5B1.381 (3)
C4A—C7A1.503 (3)C4B—C7B1.506 (3)
C5A—C6A1.381 (3)C5B—C6B1.375 (3)
C5A—H5A0.9300C5B—H5B0.9300
C6A—H6A0.9300C6B—H6B0.9300
C7A—H7A0.9600C7B—H7G0.9600
C7A—H7B0.9600C7B—H7H0.9600
C7A—H7C0.9600C7B—H7I0.9600
C7A—H7D0.9600C7B—H7J0.9600
C7A—H7E0.9600C7B—H7K0.9600
C7A—H7F0.9600C7B—H7L0.9600
C11A—C16A1.374 (3)C11B—C16B1.373 (3)
C11A—C12A1.375 (3)C11B—C12B1.375 (3)
C12A—C13A1.376 (3)C12B—C13B1.387 (3)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.370 (3)C13B—C14B1.381 (3)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.371 (3)C14B—C15B1.377 (3)
C14A—C17A1.511 (3)C14B—C17B1.503 (3)
C15A—C16A1.383 (3)C15B—C16B1.375 (3)
C15A—H15A0.9300C15B—H15B0.9300
C16A—H16A0.9300C16B—H16B0.9300
C17A—H17A0.9600C17B—H17G0.9600
C17A—H17B0.9600C17B—H17H0.9600
C17A—H17C0.9600C17B—H17I0.9600
C17A—H17D0.9600C17B—H17J0.9600
C17A—H17E0.9600C17B—H17K0.9600
C17A—H17F0.9600C17B—H17L0.9600
O2A—S1A—O1A119.00 (10)O2B—S1B—O1B119.38 (11)
O2A—S1A—C11A107.57 (10)O2B—S1B—C1B108.66 (10)
O1A—S1A—C11A108.34 (10)O1B—S1B—C1B108.77 (11)
O2A—S1A—C1A108.14 (10)O2B—S1B—C11B107.76 (10)
O1A—S1A—C1A107.86 (10)O1B—S1B—C11B108.07 (10)
C11A—S1A—C1A105.09 (9)C1B—S1B—C11B102.98 (9)
C6A—C1A—C2A119.3 (2)C2B—C1B—C6B120.0 (2)
C6A—C1A—S1A120.44 (16)C2B—C1B—S1B120.06 (18)
C2A—C1A—S1A120.24 (17)C6B—C1B—S1B119.82 (18)
C3A—C2A—C1A119.7 (2)C3B—C2B—C1B119.0 (2)
C3A—C2A—H2A120.1C3B—C2B—H2B120.5
C1A—C2A—H2A120.1C1B—C2B—H2B120.5
C2A—C3A—C4A121.9 (2)C4B—C3B—C2B122.4 (2)
C2A—C3A—H3A119.0C4B—C3B—H3B118.8
C4A—C3A—H3A119.0C2B—C3B—H3B118.8
C3A—C4A—C5A117.7 (2)C3B—C4B—C5B117.4 (2)
C3A—C4A—C7A121.3 (2)C3B—C4B—C7B121.9 (3)
C5A—C4A—C7A121.1 (2)C5B—C4B—C7B120.7 (3)
C4A—C5A—C6A121.5 (2)C6B—C5B—C4B121.8 (2)
C4A—C5A—H5A119.3C6B—C5B—H5B119.1
C6A—C5A—H5A119.3C4B—C5B—H5B119.1
C1A—C6A—C5A119.9 (2)C5B—C6B—C1B119.4 (2)
C1A—C6A—H6A120.1C5B—C6B—H6B120.3
C5A—C6A—H6A120.1C1B—C6B—H6B120.3
C4A—C7A—H7A109.5C4B—C7B—H7G109.5
C4A—C7A—H7B109.5C4B—C7B—H7H109.5
H7A—C7A—H7B109.5H7G—C7B—H7H109.5
C4A—C7A—H7C109.5C4B—C7B—H7I109.5
H7A—C7A—H7C109.5H7G—C7B—H7I109.5
H7B—C7A—H7C109.5H7H—C7B—H7I109.5
C4A—C7A—H7D109.5C4B—C7B—H7J109.5
H7A—C7A—H7D141.1H7G—C7B—H7J141.1
H7B—C7A—H7D56.3H7H—C7B—H7J56.3
H7C—C7A—H7D56.3H7I—C7B—H7J56.3
C4A—C7A—H7E109.5C4B—C7B—H7K109.5
H7A—C7A—H7E56.3H7G—C7B—H7K56.3
H7B—C7A—H7E141.1H7H—C7B—H7K141.1
H7C—C7A—H7E56.3H7I—C7B—H7K56.3
H7D—C7A—H7E109.5H7J—C7B—H7K109.5
C4A—C7A—H7F109.5C4B—C7B—H7L109.5
H7A—C7A—H7F56.3H7G—C7B—H7L56.3
H7B—C7A—H7F56.3H7H—C7B—H7L56.3
H7C—C7A—H7F141.1H7I—C7B—H7L141.1
H7D—C7A—H7F109.5H7J—C7B—H7L109.5
H7E—C7A—H7F109.5H7K—C7B—H7L109.5
C16A—C11A—C12A119.2 (2)C16B—C11B—C12B120.0 (2)
C16A—C11A—S1A120.11 (17)C16B—C11B—S1B120.39 (17)
C12A—C11A—S1A120.71 (18)C12B—C11B—S1B119.49 (17)
C11A—C12A—C13A119.7 (2)C11B—C12B—C13B119.1 (2)
C11A—C12A—H12A120.1C11B—C12B—H12B120.5
C13A—C12A—H12A120.1C13B—C12B—H12B120.5
C14A—C13A—C12A122.1 (2)C14B—C13B—C12B121.8 (2)
C14A—C13A—H13A118.9C14B—C13B—H13B119.1
C12A—C13A—H13A118.9C12B—C13B—H13B119.1
C13A—C14A—C15A117.4 (2)C15B—C14B—C13B117.5 (2)
C13A—C14A—C17A121.4 (3)C15B—C14B—C17B121.9 (2)
C15A—C14A—C17A121.1 (3)C13B—C14B—C17B120.6 (2)
C14A—C15A—C16A121.6 (2)C16B—C15B—C14B121.7 (2)
C14A—C15A—H15A119.2C16B—C15B—H15B119.2
C16A—C15A—H15A119.2C14B—C15B—H15B119.2
C11A—C16A—C15A119.9 (2)C11B—C16B—C15B119.9 (2)
C11A—C16A—H16A120.0C11B—C16B—H16B120.0
C15A—C16A—H16A120.0C15B—C16B—H16B120.0
C14A—C17A—H17A109.5C14B—C17B—H17G109.5
C14A—C17A—H17B109.5C14B—C17B—H17H109.5
H17A—C17A—H17B109.5H17G—C17B—H17H109.5
C14A—C17A—H17C109.5C14B—C17B—H17I109.5
H17A—C17A—H17C109.5H17G—C17B—H17I109.5
H17B—C17A—H17C109.5H17H—C17B—H17I109.5
C14A—C17A—H17D109.5C14B—C17B—H17J109.5
H17A—C17A—H17D141.1H17G—C17B—H17J141.1
H17B—C17A—H17D56.3H17H—C17B—H17J56.3
H17C—C17A—H17D56.3H17I—C17B—H17J56.3
C14A—C17A—H17E109.5C14B—C17B—H17K109.5
H17A—C17A—H17E56.3H17G—C17B—H17K56.3
H17B—C17A—H17E141.1H17H—C17B—H17K141.1
H17C—C17A—H17E56.3H17I—C17B—H17K56.3
H17D—C17A—H17E109.5H17J—C17B—H17K109.5
C14A—C17A—H17F109.5C14B—C17B—H17L109.5
H17A—C17A—H17F56.3H17G—C17B—H17L56.3
H17B—C17A—H17F56.3H17H—C17B—H17L56.3
H17C—C17A—H17F141.1H17I—C17B—H17L141.1
H17D—C17A—H17F109.5H17J—C17B—H17L109.5
H17E—C17A—H17F109.5H17K—C17B—H17L109.5
O2A—S1A—C1A—C6A139.65 (17)O2B—S1B—C1B—C2B27.01 (19)
O1A—S1A—C1A—C6A9.7 (2)O1B—S1B—C1B—C2B158.44 (17)
C11A—S1A—C1A—C6A105.68 (18)C11B—S1B—C1B—C2B87.08 (18)
O2A—S1A—C1A—C2A39.45 (19)O2B—S1B—C1B—C6B157.39 (17)
O1A—S1A—C1A—C2A169.37 (16)O1B—S1B—C1B—C6B26.0 (2)
C11A—S1A—C1A—C2A75.22 (18)C11B—S1B—C1B—C6B88.52 (18)
C6A—C1A—C2A—C3A0.2 (3)C6B—C1B—C2B—C3B0.4 (3)
S1A—C1A—C2A—C3A179.32 (17)S1B—C1B—C2B—C3B175.19 (16)
C1A—C2A—C3A—C4A1.0 (3)C1B—C2B—C3B—C4B0.1 (3)
C2A—C3A—C4A—C5A0.7 (3)C2B—C3B—C4B—C5B0.6 (3)
C2A—C3A—C4A—C7A179.8 (2)C2B—C3B—C4B—C7B178.2 (2)
C3A—C4A—C5A—C6A0.5 (3)C3B—C4B—C5B—C6B1.0 (3)
C7A—C4A—C5A—C6A178.6 (2)C7B—C4B—C5B—C6B177.8 (2)
C2A—C1A—C6A—C5A1.0 (3)C4B—C5B—C6B—C1B0.7 (3)
S1A—C1A—C6A—C5A178.16 (16)C2B—C1B—C6B—C5B0.0 (3)
C4A—C5A—C6A—C1A1.3 (3)S1B—C1B—C6B—C5B175.57 (16)
O2A—S1A—C11A—C16A150.93 (17)O2B—S1B—C11B—C16B148.83 (17)
O1A—S1A—C11A—C16A21.1 (2)O1B—S1B—C11B—C16B18.6 (2)
C1A—S1A—C11A—C16A94.00 (18)C1B—S1B—C11B—C16B96.43 (18)
O2A—S1A—C11A—C12A29.8 (2)O2B—S1B—C11B—C12B34.23 (19)
O1A—S1A—C11A—C12A159.66 (17)O1B—S1B—C11B—C12B164.49 (16)
C1A—S1A—C11A—C12A85.25 (19)C1B—S1B—C11B—C12B80.52 (18)
C16A—C11A—C12A—C13A0.5 (3)C16B—C11B—C12B—C13B0.1 (3)
S1A—C11A—C12A—C13A178.80 (17)S1B—C11B—C12B—C13B176.85 (16)
C11A—C12A—C13A—C14A0.1 (4)C11B—C12B—C13B—C14B0.1 (3)
C12A—C13A—C14A—C15A0.9 (4)C12B—C13B—C14B—C15B0.6 (3)
C12A—C13A—C14A—C17A177.8 (2)C12B—C13B—C14B—C17B179.2 (2)
C13A—C14A—C15A—C16A1.2 (4)C13B—C14B—C15B—C16B0.8 (3)
C17A—C14A—C15A—C16A177.5 (2)C17B—C14B—C15B—C16B179.0 (2)
C12A—C11A—C16A—C15A0.2 (3)C12B—C11B—C16B—C15B0.1 (3)
S1A—C11A—C16A—C15A179.04 (17)S1B—C11B—C16B—C15B177.06 (17)
C14A—C15A—C16A—C11A0.6 (4)C14B—C15B—C16B—C11B0.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15A—H15A···O2Ai0.932.443.354 (3)166
C5B—H5B···O2Bi0.932.583.317 (3)137
Symmetry code: (i) x, y+1, z.
(2) 2,5,4'-Trimethyldiphenyl sulfone top
Crystal data top
C15H16O2SF(000) = 552
Mr = 260.34Dx = 1.283 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.3374 (6) ÅCell parameters from 12210 reflections
b = 14.9785 (8) Åθ = 2.3–27.4°
c = 10.9064 (6) ŵ = 0.23 mm1
β = 98.241 (3)°T = 150 K
V = 1347.95 (14) Å3Plate, colourless
Z = 40.2 × 0.2 × 0.03 mm
Data collection top
Kappa-CCD
diffractometer
3060 independent reflections
Radiation source: fine-focus sealed X-ray tube2172 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ϕ scans and ω scans with κ offsetsθmax = 27.4°, θmin = 2.3°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 1010
Tmin = 0.929, Tmax = 0.969k = 1819
12210 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1788P]
where P = (Fo2 + 2Fc2)/3
3060 reflections(Δ/σ)max = 0.005
166 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C15H16O2SV = 1347.95 (14) Å3
Mr = 260.34Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.3374 (6) ŵ = 0.23 mm1
b = 14.9785 (8) ÅT = 150 K
c = 10.9064 (6) Å0.2 × 0.2 × 0.03 mm
β = 98.241 (3)°
Data collection top
Kappa-CCD
diffractometer
3060 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
2172 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 0.969Rint = 0.037
12210 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.04Δρmax = 0.24 e Å3
3060 reflectionsΔρmin = 0.44 e Å3
166 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.46216 (6)0.31838 (3)0.09163 (4)0.02781 (17)
O10.49354 (17)0.22681 (8)0.12618 (13)0.0369 (4)
O20.53037 (16)0.35246 (9)0.01306 (12)0.0342 (3)
C10.5347 (2)0.38672 (12)0.21938 (16)0.0267 (4)
C20.5118 (2)0.47859 (12)0.21014 (17)0.0300 (4)
H20.45040.50310.14030.036*
C30.5803 (2)0.53284 (13)0.30477 (18)0.0336 (5)
H30.56370.59420.29850.040*
C40.6744 (2)0.49798 (13)0.41049 (17)0.0331 (5)
C410.7522 (3)0.55939 (15)0.51092 (19)0.0470 (6)
H140.67620.57280.56660.071*
H240.78440.61370.47450.071*
H340.84580.53090.55580.071*
C50.6946 (3)0.40644 (14)0.41791 (18)0.0383 (5)
H50.75660.38200.48750.046*
C60.6248 (3)0.35026 (13)0.32433 (18)0.0348 (5)
H60.63810.28880.33170.042*
C1A0.2503 (2)0.33652 (11)0.05977 (16)0.0248 (4)
C2A0.1421 (2)0.30131 (12)0.13526 (17)0.0292 (4)
C21A0.19468 (18)0.24921 (13)0.25158 (15)0.0376 (5)
H12A0.10900.24880.30170.056*
H22A0.28930.27640.29690.056*
H32A0.21940.18900.23060.056*
C3A0.02068 (18)0.31750 (12)0.09638 (14)0.0337 (5)
H3A0.09640.29480.14300.040*
C4A0.0749 (2)0.36618 (13)0.00909 (18)0.0342 (5)
H4A0.18560.37500.03170.041*
C5A0.0323 (2)0.40230 (12)0.08212 (17)0.0290 (4)
C51A0.0249 (3)0.45567 (14)0.19734 (18)0.0373 (5)
H15A0.05470.50010.20870.056*
H25A0.12570.48440.18890.056*
H35A0.04010.41660.26780.056*
C6A0.1956 (2)0.38638 (12)0.04544 (16)0.0274 (4)
H6A0.27060.40960.09230.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0264 (3)0.0284 (3)0.0290 (3)0.00289 (19)0.0052 (2)0.0013 (2)
O10.0396 (9)0.0261 (7)0.0440 (8)0.0065 (6)0.0024 (7)0.0003 (6)
O20.0275 (8)0.0470 (9)0.0301 (7)0.0032 (6)0.0108 (6)0.0046 (6)
C10.0244 (10)0.0288 (10)0.0276 (10)0.0010 (8)0.0065 (8)0.0039 (8)
C20.0279 (11)0.0310 (10)0.0305 (10)0.0007 (8)0.0023 (8)0.0066 (8)
C30.0371 (12)0.0267 (10)0.0371 (11)0.0019 (9)0.0060 (9)0.0031 (9)
C40.0312 (11)0.0379 (11)0.0303 (10)0.0065 (9)0.0044 (9)0.0018 (9)
C410.0509 (15)0.0494 (14)0.0386 (12)0.0123 (11)0.0011 (11)0.0022 (10)
C50.0406 (13)0.0393 (12)0.0320 (11)0.0013 (10)0.0049 (9)0.0107 (9)
C60.0404 (13)0.0279 (10)0.0346 (11)0.0011 (9)0.0002 (9)0.0079 (9)
C1A0.0245 (10)0.0246 (9)0.0254 (9)0.0012 (7)0.0041 (8)0.0036 (7)
C2A0.0321 (11)0.0253 (9)0.0306 (10)0.0050 (8)0.0067 (8)0.0039 (8)
C21A0.0412 (13)0.0401 (11)0.0326 (11)0.0068 (10)0.0089 (9)0.0053 (9)
C3A0.0305 (12)0.0355 (11)0.0371 (11)0.0084 (9)0.0118 (9)0.0056 (9)
C4A0.0241 (11)0.0360 (11)0.0412 (12)0.0005 (9)0.0008 (9)0.0092 (9)
C5A0.0307 (11)0.0249 (10)0.0304 (10)0.0020 (8)0.0011 (8)0.0072 (8)
C51A0.0395 (13)0.0343 (11)0.0353 (11)0.0037 (9)0.0046 (9)0.0025 (9)
C6A0.0289 (11)0.0250 (9)0.0285 (10)0.0014 (8)0.0050 (8)0.0031 (8)
Geometric parameters (Å, º) top
S1—O11.4363 (13)C1A—C6A1.390 (3)
S1—O21.4400 (13)C1A—C2A1.408 (2)
S1—C11.7644 (19)C2A—C3A1.384 (2)
S1—C1A1.7716 (19)C2A—C21A1.500 (2)
C1—C61.388 (3)C21A—H12A0.9600
C1—C21.391 (3)C21A—H22A0.9600
C2—C31.372 (3)C21A—H32A0.9600
C2—H20.9300C3A—C4A1.382 (2)
C3—C41.399 (3)C3A—H3A0.9300
C3—H30.9300C4A—C5A1.389 (3)
C4—C51.382 (3)C4A—H4A0.9300
C4—C411.505 (3)C5A—C6A1.384 (3)
C41—H140.9600C5A—C51A1.508 (3)
C41—H240.9600C51A—H15A0.9600
C41—H340.9600C51A—H25A0.9600
C5—C61.385 (3)C51A—H35A0.9600
C5—H50.9300C6A—H6A0.9300
C6—H60.9300
O1—S1—O2117.95 (8)C6A—C1A—C2A121.48 (18)
O1—S1—C1108.53 (8)C6A—C1A—S1116.37 (13)
O2—S1—C1106.91 (8)C2A—C1A—S1122.15 (14)
O1—S1—C1A109.69 (8)C3A—C2A—C1A115.94 (16)
O2—S1—C1A106.62 (8)C3A—C2A—C21A120.33 (15)
C1—S1—C1A106.56 (8)C1A—C2A—C21A123.73 (17)
C6—C1—C2120.10 (18)C2A—C21A—H12A109.5
C6—C1—S1120.45 (15)C2A—C21A—H22A109.5
C2—C1—S1119.26 (14)H12A—C21A—H22A109.5
C3—C2—C1119.56 (18)C2A—C21A—H32A109.5
C3—C2—H2120.2H12A—C21A—H32A109.5
C1—C2—H2120.2H22A—C21A—H32A109.5
C2—C3—C4121.50 (18)C4A—C3A—C2A122.47 (14)
C2—C3—H3119.2C4A—C3A—H3A118.8
C4—C3—H3119.2C2A—C3A—H3A118.8
C5—C4—C3117.88 (18)C3A—C4A—C5A121.48 (18)
C5—C4—C41121.84 (18)C3A—C4A—H4A119.3
C3—C4—C41120.28 (18)C5A—C4A—H4A119.3
C4—C41—H14109.5C6A—C5A—C4A117.02 (18)
C4—C41—H24109.5C6A—C5A—C51A120.83 (17)
H14—C41—H24109.5C4A—C5A—C51A122.14 (18)
C4—C41—H34109.5C5A—C51A—H15A109.5
H14—C41—H34109.5C5A—C51A—H25A109.5
H24—C41—H34109.5H15A—C51A—H25A109.5
C4—C5—C6121.64 (18)C5A—C51A—H35A109.5
C4—C5—H5119.2H15A—C51A—H35A109.5
C6—C5—H5119.2H25A—C51A—H35A109.5
C5—C6—C1119.30 (18)C5A—C6A—C1A121.59 (17)
C5—C6—H6120.4C5A—C6A—H6A119.2
C1—C6—H6120.4C1A—C6A—H6A119.2
O1—S1—C1—C67.81 (18)C1—S1—C1A—C6A106.81 (14)
O2—S1—C1—C6120.40 (16)O1—S1—C1A—C2A43.05 (17)
C1A—S1—C1—C6125.87 (16)O2—S1—C1A—C2A171.83 (14)
O1—S1—C1—C2177.27 (14)C1—S1—C1A—C2A74.25 (16)
O2—S1—C1—C254.51 (16)C6A—C1A—C2A—C3A1.6 (3)
C1A—S1—C1—C259.21 (16)S1—C1A—C2A—C3A177.30 (13)
C6—C1—C2—C30.7 (3)C6A—C1A—C2A—C21A178.28 (17)
S1—C1—C2—C3174.23 (14)S1—C1A—C2A—C21A2.8 (3)
C1—C2—C3—C40.6 (3)C1A—C2A—C3A—C4A0.8 (3)
C2—C3—C4—C51.0 (3)C21A—C2A—C3A—C4A179.07 (17)
C2—C3—C4—C41178.06 (18)C2A—C3A—C4A—C5A0.4 (3)
C3—C4—C5—C60.1 (3)C3A—C4A—C5A—C6A0.8 (3)
C41—C4—C5—C6178.95 (19)C3A—C4A—C5A—C51A179.91 (17)
C4—C5—C6—C11.2 (3)C4A—C5A—C6A—C1A0.0 (3)
C2—C1—C6—C51.6 (3)C51A—C5A—C6A—C1A179.30 (16)
S1—C1—C6—C5173.29 (15)C2A—C1A—C6A—C5A1.2 (3)
O1—S1—C1A—C6A135.89 (14)S1—C1A—C6A—C5A177.74 (14)
O2—S1—C1A—C6A7.11 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A···O2i0.932.433.292 (2)154
C2—H2···O2ii0.932.593.306 (2)134
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z.
(3) 4-Chlorodiphenyl sulfone top
Crystal data top
C12H9ClO2SF(000) = 520
Mr = 252.70Dx = 1.452 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.239 (3) ÅCell parameters from 3848 reflections
b = 7.4521 (15) Åθ = 1.5–25.0°
c = 11.737 (2) ŵ = 0.49 mm1
β = 93.17 (3)°T = 307 K
V = 1156.3 (4) Å3Block, yellow
Z = 40.40 × 0.28 × 0.24 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
2030 independent reflections
Radiation source: fine-focus sealed X-ray tube1527 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ϕ scans and ω scans with κ offsetsθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
SADABS (Bruker, 1997)
h = 1515
Tmin = 0.828, Tmax = 0.891k = 88
7000 measured reflectionsl = 813
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.055P)2 + 0.2889P]
where P = (Fo2 + 2Fc2)/3
2030 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C12H9ClO2SV = 1156.3 (4) Å3
Mr = 252.70Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.239 (3) ŵ = 0.49 mm1
b = 7.4521 (15) ÅT = 307 K
c = 11.737 (2) Å0.40 × 0.28 × 0.24 mm
β = 93.17 (3)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
2030 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 1997)
1527 reflections with I > 2σ(I)
Tmin = 0.828, Tmax = 0.891Rint = 0.020
7000 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.04Δρmax = 0.24 e Å3
2030 reflectionsΔρmin = 0.40 e Å3
145 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.22766 (5)0.17244 (9)0.31273 (5)0.0624 (2)
O10.26580 (14)0.3492 (3)0.3348 (2)0.0916 (7)
O20.22962 (14)0.0990 (3)0.19946 (14)0.0889 (7)
C10.10107 (16)0.1681 (3)0.35280 (17)0.0464 (5)
C20.02900 (17)0.0831 (3)0.28305 (19)0.0549 (6)
C30.07109 (18)0.0891 (3)0.3102 (2)0.0627 (6)
C40.09809 (19)0.1760 (3)0.4071 (2)0.0618 (6)
C50.0253 (2)0.2571 (4)0.4773 (2)0.0639 (7)
C60.07406 (18)0.2552 (3)0.45115 (19)0.0580 (6)
C1A0.29383 (16)0.0241 (3)0.40809 (18)0.0520 (6)
C2A0.33534 (19)0.0875 (4)0.5104 (2)0.0659 (7)
C3A0.38710 (19)0.0305 (5)0.5835 (2)0.0762 (8)
C4A0.39620 (18)0.2070 (4)0.5527 (2)0.0680 (7)
Cl4A0.46364 (7)0.35274 (15)0.64329 (8)0.1160 (4)
C5A0.35342 (19)0.2712 (4)0.4519 (2)0.0691 (7)
C6A0.30174 (18)0.1543 (3)0.3793 (2)0.0613 (6)
H20.04760.02230.21830.066*
H30.12040.03410.26260.075*
H40.16560.18000.42510.074*
H50.04380.31410.54350.077*
H60.12290.31140.49860.070*
H2A0.32870.20760.53000.079*
H3A0.41560.00970.65310.091*
H5A0.35930.39170.43290.083*
H6A0.27200.19580.31060.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0467 (3)0.0727 (4)0.0678 (4)0.0047 (3)0.0051 (3)0.0227 (3)
O10.0559 (11)0.0725 (13)0.1453 (19)0.0105 (9)0.0044 (11)0.0385 (12)
O20.0734 (12)0.1423 (19)0.0526 (10)0.0288 (12)0.0180 (9)0.0229 (11)
C10.0440 (12)0.0468 (11)0.0480 (11)0.0028 (9)0.0003 (9)0.0095 (9)
C20.0586 (14)0.0534 (13)0.0524 (13)0.0033 (11)0.0004 (10)0.0062 (10)
C30.0541 (14)0.0563 (14)0.0763 (16)0.0094 (11)0.0083 (12)0.0021 (12)
C40.0511 (14)0.0621 (14)0.0732 (16)0.0009 (12)0.0133 (12)0.0145 (13)
C50.0709 (17)0.0710 (16)0.0507 (14)0.0097 (13)0.0121 (12)0.0020 (11)
C60.0587 (14)0.0634 (14)0.0507 (13)0.0001 (12)0.0067 (11)0.0044 (11)
C1A0.0401 (11)0.0610 (14)0.0550 (13)0.0028 (10)0.0052 (10)0.0088 (11)
C2A0.0554 (14)0.0689 (16)0.0723 (16)0.0025 (12)0.0069 (12)0.0048 (13)
C3A0.0550 (15)0.113 (2)0.0588 (15)0.0045 (15)0.0095 (12)0.0023 (15)
C4A0.0428 (13)0.093 (2)0.0693 (16)0.0176 (13)0.0111 (11)0.0258 (15)
Cl4A0.0774 (5)0.1677 (9)0.1037 (6)0.0516 (6)0.0129 (4)0.0652 (6)
C5A0.0613 (15)0.0667 (16)0.0803 (18)0.0162 (13)0.0118 (13)0.0058 (14)
C6A0.0552 (14)0.0716 (16)0.0571 (14)0.0080 (12)0.0035 (11)0.0035 (12)
Geometric parameters (Å, º) top
S1—O11.429 (2)C5—H50.9300
S1—O21.439 (2)C6—H60.9300
S1—C11.766 (2)C1A—C2A1.376 (3)
S1—C1A1.770 (2)C1A—C6A1.377 (3)
C1—C21.377 (3)C2A—C3A1.383 (4)
C1—C61.388 (3)C2A—H2A0.9300
C2—C31.381 (3)C3A—C4A1.371 (4)
C2—H20.9300C3A—H3A0.9300
C3—C41.373 (4)C4A—C5A1.370 (4)
C3—H30.9300C4A—Cl4A1.733 (2)
C4—C51.374 (3)C5A—C6A1.374 (3)
C4—H40.9300C5A—H5A0.9300
C5—C61.367 (3)C6A—H6A0.9300
O1—S1—O2119.58 (14)C5—C6—C1119.2 (2)
O1—S1—C1107.43 (11)C5—C6—H6120.4
O2—S1—C1107.76 (11)C1—C6—H6120.4
O1—S1—C1A107.66 (12)C2A—C1A—C6A120.9 (2)
O2—S1—C1A108.25 (12)C2A—C1A—S1119.79 (19)
C1—S1—C1A105.30 (10)C6A—C1A—S1119.31 (18)
C2—C1—C6120.5 (2)C1A—C2A—C3A118.9 (3)
C2—C1—S1119.13 (17)C1A—C2A—H2A120.6
C6—C1—S1120.32 (17)C3A—C2A—H2A120.6
C1—C2—C3119.4 (2)C4A—C3A—C2A119.6 (2)
C1—C2—H2120.3C4A—C3A—H3A120.2
C3—C2—H2120.3C2A—C3A—H3A120.2
C4—C3—C2120.2 (2)C5A—C4A—C3A121.6 (2)
C4—C3—H3119.9C5A—C4A—Cl4A119.1 (2)
C2—C3—H3119.9C3A—C4A—Cl4A119.3 (2)
C3—C4—C5119.9 (2)C4A—C5A—C6A118.8 (3)
C3—C4—H4120.0C4A—C5A—H5A120.6
C5—C4—H4120.0C6A—C5A—H5A120.6
C6—C5—C4120.8 (2)C5A—C6A—C1A120.1 (2)
C6—C5—H5119.6C5A—C6A—H6A119.9
C4—C5—H5119.6C1A—C6A—H6A119.9
O1—S1—C1—C2137.28 (18)O2—S1—C1A—C2A156.2 (2)
O2—S1—C1—C27.2 (2)C1—S1—C1A—C2A88.8 (2)
C1A—S1—C1—C2108.17 (18)O1—S1—C1A—C6A155.3 (2)
O1—S1—C1—C640.3 (2)O2—S1—C1A—C6A24.7 (2)
O2—S1—C1—C6170.36 (18)C1—S1—C1A—C6A90.3 (2)
C1A—S1—C1—C674.3 (2)C6A—C1A—C2A—C3A1.2 (4)
C6—C1—C2—C31.7 (3)S1—C1A—C2A—C3A179.7 (2)
S1—C1—C2—C3175.89 (18)C1A—C2A—C3A—C4A0.2 (4)
C1—C2—C3—C41.3 (4)C2A—C3A—C4A—C5A1.3 (4)
C2—C3—C4—C50.1 (4)C2A—C3A—C4A—Cl4A178.5 (2)
C3—C4—C5—C61.1 (4)C3A—C4A—C5A—C6A1.1 (4)
C4—C5—C6—C10.7 (4)Cl4A—C4A—C5A—C6A178.73 (19)
C2—C1—C6—C50.7 (3)C4A—C5A—C6A—C1A0.2 (4)
S1—C1—C6—C5176.85 (18)C2A—C1A—C6A—C5A1.4 (4)
O1—S1—C1A—C2A25.6 (2)S1—C1A—C6A—C5A179.52 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.583.500 (3)169
C5A—H5A···O1ii0.932.533.326 (4)143
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y1, z.
(4) 3,4-Dimethyl-4'-chlorodiphenyl sulfone top
Crystal data top
C14H13ClO2SF(000) = 584
Mr = 280.75Dx = 1.411 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.9682 (14) ÅCell parameters from 9255 reflections
b = 7.5293 (12) Åθ = 1.8–25.9°
c = 14.4627 (17) ŵ = 0.44 mm1
β = 110.625 (7)°T = 150 K
V = 1321.6 (3) Å3Block, colourless
Z = 40.10 × 0.08 × 0.05 mm
Data collection top
Kappa-CCD
diffractometer
2545 independent reflections
Radiation source: fine-focus sealed X-ray tube1332 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
ϕ scans and ω scans with κ offsetsθmax = 25.9°, θmin = 1.8°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 1515
Tmin = 0.958, Tmax = 0.979k = 99
9255 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.076P)2]
where P = (Fo2 + 2Fc2)/3
2545 reflections(Δ/σ)max = 0.003
165 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C14H13ClO2SV = 1321.6 (3) Å3
Mr = 280.75Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.9682 (14) ŵ = 0.44 mm1
b = 7.5293 (12) ÅT = 150 K
c = 14.4627 (17) Å0.10 × 0.08 × 0.05 mm
β = 110.625 (7)°
Data collection top
Kappa-CCD
diffractometer
2545 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
1332 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.979Rint = 0.053
9255 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 0.93Δρmax = 0.34 e Å3
2545 reflectionsΔρmin = 0.28 e Å3
165 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.64115 (7)0.17336 (16)0.84103 (7)0.0488 (4)
O10.6176 (2)0.3456 (4)0.87187 (19)0.0609 (8)
O20.74906 (17)0.0979 (4)0.88738 (17)0.0625 (9)
C10.6138 (3)0.1842 (5)0.7133 (2)0.0378 (9)
C20.5246 (3)0.2793 (6)0.6537 (3)0.0468 (11)
H20.47850.34010.68190.056*
C30.5015 (3)0.2870 (6)0.5527 (3)0.0497 (11)
H30.43940.35100.51090.060*
C40.5703 (3)0.2002 (6)0.5142 (2)0.0436 (10)
Cl40.54225 (8)0.21027 (17)0.38745 (7)0.0634 (4)
C50.6595 (3)0.1037 (6)0.5717 (3)0.0475 (10)
H50.70540.04410.54300.057*
C60.6816 (3)0.0947 (6)0.6732 (3)0.0468 (10)
H60.74260.02790.71450.056*
C1A0.5443 (3)0.0221 (6)0.8552 (2)0.0442 (10)
C2A0.4469 (3)0.0854 (6)0.8613 (2)0.0488 (11)
H2A0.43360.20970.85880.059*
C3A0.3672 (3)0.0319 (7)0.8711 (2)0.0508 (11)
C31A0.2618 (3)0.0406 (8)0.8757 (3)0.0786 (17)
H13A0.19960.00820.82110.118*
H23A0.26190.17040.87020.118*
H33A0.25480.00730.93870.118*
C4A0.3885 (3)0.2130 (7)0.8747 (2)0.0555 (12)
C41A0.3031 (4)0.3431 (7)0.8836 (3)0.0745 (15)
H14A0.28600.31560.94290.112*
H24A0.33210.46420.88840.112*
H34A0.23590.33340.82510.112*
C5A0.4869 (4)0.2747 (7)0.8702 (3)0.0644 (13)
H5A0.50110.39870.87400.077*
C6A0.5656 (3)0.1583 (7)0.8602 (2)0.0539 (12)
H6A0.63290.20200.85670.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0390 (5)0.0710 (9)0.0320 (5)0.0065 (5)0.0068 (4)0.0049 (5)
O10.0668 (17)0.066 (2)0.0502 (16)0.0067 (16)0.0216 (14)0.0174 (15)
O20.0336 (14)0.104 (3)0.0393 (15)0.0012 (15)0.0005 (11)0.0047 (15)
C10.0293 (17)0.048 (3)0.0330 (18)0.0064 (17)0.0065 (15)0.0031 (18)
C20.035 (2)0.060 (3)0.044 (2)0.0017 (19)0.0130 (18)0.002 (2)
C30.0357 (19)0.062 (3)0.043 (2)0.0065 (19)0.0038 (18)0.008 (2)
C40.043 (2)0.053 (3)0.0322 (19)0.0164 (19)0.0097 (17)0.0033 (18)
Cl40.0670 (7)0.0837 (10)0.0361 (6)0.0220 (6)0.0138 (5)0.0003 (5)
C50.042 (2)0.056 (3)0.047 (2)0.0066 (19)0.0184 (18)0.006 (2)
C60.0374 (19)0.061 (3)0.039 (2)0.0031 (19)0.0096 (17)0.005 (2)
C1A0.037 (2)0.062 (3)0.0275 (19)0.006 (2)0.0045 (15)0.0042 (19)
C2A0.045 (2)0.069 (3)0.0278 (19)0.011 (2)0.0073 (16)0.0081 (19)
C3A0.038 (2)0.082 (4)0.0282 (19)0.002 (2)0.0069 (15)0.004 (2)
C31A0.059 (3)0.126 (5)0.054 (3)0.010 (3)0.026 (2)0.015 (3)
C4A0.050 (2)0.090 (4)0.025 (2)0.010 (3)0.0104 (17)0.002 (2)
C41A0.088 (3)0.095 (5)0.043 (2)0.030 (3)0.027 (2)0.008 (2)
C5A0.081 (3)0.066 (4)0.038 (2)0.002 (3)0.009 (2)0.002 (2)
C6A0.048 (2)0.074 (4)0.035 (2)0.001 (2)0.0094 (18)0.002 (2)
Geometric parameters (Å, º) top
S1—O21.439 (3)C1A—C6A1.383 (6)
S1—O11.439 (3)C2A—C3A1.403 (6)
S1—C11.756 (3)C2A—H2A0.9500
S1—C1A1.760 (4)C3A—C4A1.388 (6)
C1—C21.376 (5)C3A—C31A1.496 (5)
C1—C61.387 (5)C31A—H13A0.9800
C2—C31.385 (5)C31A—H23A0.9800
C2—H20.9500C31A—H33A0.9800
C3—C41.372 (5)C4A—C5A1.382 (6)
C3—H30.9500C4A—C41A1.517 (6)
C4—C51.371 (5)C41A—H14A0.9800
C4—Cl41.741 (3)C41A—H24A0.9800
C5—C61.394 (5)C41A—H34A0.9800
C5—H50.9500C5A—C6A1.391 (6)
C6—H60.9500C5A—H5A0.9500
C1A—C2A1.382 (5)C6A—H6A0.9500
O2—S1—O1119.32 (17)C1A—C2A—C3A120.7 (4)
O2—S1—C1108.17 (16)C1A—C2A—H2A119.6
O1—S1—C1107.33 (17)C3A—C2A—H2A119.6
O2—S1—C1A107.87 (18)C4A—C3A—C2A118.6 (4)
O1—S1—C1A107.98 (18)C4A—C3A—C31A122.0 (4)
C1—S1—C1A105.34 (15)C2A—C3A—C31A119.4 (5)
C2—C1—C6120.5 (3)C3A—C31A—H13A109.5
C2—C1—S1119.9 (3)C3A—C31A—H23A109.5
C6—C1—S1119.6 (3)H13A—C31A—H23A109.5
C1—C2—C3120.3 (4)C3A—C31A—H33A109.5
C1—C2—H2119.9H13A—C31A—H33A109.5
C3—C2—H2119.9H23A—C31A—H33A109.5
C4—C3—C2118.6 (3)C5A—C4A—C3A120.2 (4)
C4—C3—H3120.7C5A—C4A—C41A120.1 (5)
C2—C3—H3120.7C3A—C4A—C41A119.7 (4)
C3—C4—C5122.5 (3)C4A—C41A—H14A109.5
C3—C4—Cl4118.8 (3)C4A—C41A—H24A109.5
C5—C4—Cl4118.7 (3)H14A—C41A—H24A109.5
C4—C5—C6118.7 (4)C4A—C41A—H34A109.5
C4—C5—H5120.6H14A—C41A—H34A109.5
C6—C5—H5120.6H24A—C41A—H34A109.5
C1—C6—C5119.4 (3)C4A—C5A—C6A121.1 (5)
C1—C6—H6120.3C4A—C5A—H5A119.4
C5—C6—H6120.3C6A—C5A—H5A119.4
C2A—C1A—C6A120.4 (4)C1A—C6A—C5A118.9 (4)
C2A—C1A—S1119.4 (4)C1A—C6A—H6A120.5
C6A—C1A—S1120.2 (3)C5A—C6A—H6A120.5
O2—S1—C1—C2168.6 (3)C1—S1—C1A—C2A94.8 (3)
O1—S1—C1—C238.6 (3)O2—S1—C1A—C6A30.2 (3)
C1A—S1—C1—C276.3 (3)O1—S1—C1A—C6A160.4 (3)
O2—S1—C1—C612.2 (4)C1—S1—C1A—C6A85.1 (3)
O1—S1—C1—C6142.2 (3)C6A—C1A—C2A—C3A0.9 (5)
C1A—S1—C1—C6102.9 (3)S1—C1A—C2A—C3A179.0 (2)
C6—C1—C2—C30.1 (6)C1A—C2A—C3A—C4A0.1 (5)
S1—C1—C2—C3179.3 (3)C1A—C2A—C3A—C31A179.0 (3)
C1—C2—C3—C41.0 (6)C2A—C3A—C4A—C5A0.9 (5)
C2—C3—C4—C51.3 (6)C31A—C3A—C4A—C5A180.0 (3)
C2—C3—C4—Cl4179.7 (3)C2A—C3A—C4A—C41A179.0 (3)
C3—C4—C5—C60.5 (6)C31A—C3A—C4A—C41A0.1 (5)
Cl4—C4—C5—C6179.6 (3)C3A—C4A—C5A—C6A1.2 (6)
C2—C1—C6—C50.8 (6)C41A—C4A—C5A—C6A178.7 (3)
S1—C1—C6—C5180.0 (3)C2A—C1A—C6A—C5A0.7 (5)
C4—C5—C6—C10.5 (6)S1—C1A—C6A—C5A179.2 (3)
O2—S1—C1A—C2A149.9 (3)C4A—C5A—C6A—C1A0.4 (6)
O1—S1—C1A—C2A19.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.523.416 (5)158
C5A—H5A···O1ii0.952.453.319 (6)151
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x, y1, z.
(5) 2,5-Dimethyldiphenyl sulfone top
Crystal data top
C14H14O2SF(000) = 520
Mr = 246.31Dx = 1.274 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.8879 (3) ÅCell parameters from 14179 reflections
b = 10.9788 (4) Åθ = 2.3–27.3°
c = 15.2489 (4) ŵ = 0.24 mm1
β = 103.525 (2)°T = 150 K
V = 1283.93 (8) Å3Plate, colourless
Z = 40.20 × 0.15 × 0.05 mm
Data collection top
Kappa-CCD
diffractometer
2895 independent reflections
Radiation source: fine-focus sealed X-ray tube1990 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ scans and ω scans with κ offsetsθmax = 27.3°, θmin = 2.3°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 1010
Tmin = 0.954, Tmax = 0.988k = 1414
14179 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0642P)2 + 0.0204P]
where P = (Fo2 + 2Fc2)/3
2895 reflections(Δ/σ)max = 0.004
156 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
C14H14O2SV = 1283.93 (8) Å3
Mr = 246.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.8879 (3) ŵ = 0.24 mm1
b = 10.9788 (4) ÅT = 150 K
c = 15.2489 (4) Å0.20 × 0.15 × 0.05 mm
β = 103.525 (2)°
Data collection top
Kappa-CCD
diffractometer
2895 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
1990 reflections with I > 2σ(I)
Tmin = 0.954, Tmax = 0.988Rint = 0.038
14179 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.04Δρmax = 0.26 e Å3
2895 reflectionsΔρmin = 0.42 e Å3
156 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.19274 (6)0.75337 (4)0.29672 (3)0.02638 (17)
O10.10507 (17)0.83517 (12)0.22674 (8)0.0321 (3)
O20.34797 (16)0.69367 (13)0.28465 (8)0.0349 (4)
C10.0404 (2)0.64101 (17)0.30893 (11)0.0255 (4)
C20.1252 (2)0.67689 (19)0.31517 (12)0.0324 (5)
C30.2478 (3)0.5878 (2)0.32019 (13)0.0403 (5)
C40.2047 (3)0.4665 (2)0.31915 (13)0.0407 (5)
C50.0401 (3)0.4319 (2)0.31243 (13)0.0393 (5)
C60.0845 (3)0.51890 (18)0.30783 (12)0.0329 (5)
C1A0.2399 (2)0.83687 (17)0.39923 (11)0.0270 (4)
C2A0.3324 (3)0.7831 (2)0.48037 (12)0.0330 (5)
C2A10.3947 (3)0.6532 (2)0.48952 (13)0.0424 (6)
C3A0.3638 (3)0.8588 (2)0.55521 (13)0.0406 (5)
C4A0.3093 (3)0.9785 (2)0.55117 (13)0.0422 (6)
C5A0.2183 (3)1.0306 (2)0.47111 (12)0.0356 (5)
C5A10.1602 (3)1.1611 (2)0.46530 (15)0.0502 (6)
C6A0.1843 (2)0.95648 (19)0.39489 (12)0.0312 (5)
H20.15420.76080.31600.039*
H30.36180.61080.32440.048*
H40.28880.40610.32310.049*
H50.01210.34790.31090.047*
H60.19840.49530.30400.040*
H2A10.46310.63910.55110.064*
H2A20.46760.63760.44670.064*
H2A30.29400.59820.47670.064*
H3A0.42530.82690.61160.049*
H4A0.33461.02640.60450.051*
H5A10.22501.20550.51840.075*
H5A20.03521.16480.46320.075*
H5A30.18251.19810.41060.075*
H6A0.12170.98880.33890.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0249 (3)0.0316 (3)0.0225 (3)0.0009 (2)0.00526 (18)0.00011 (19)
O10.0359 (8)0.0346 (9)0.0229 (6)0.0027 (6)0.0011 (5)0.0035 (5)
O20.0259 (7)0.0454 (9)0.0360 (7)0.0015 (7)0.0124 (5)0.0017 (6)
C10.0232 (9)0.0327 (12)0.0197 (9)0.0015 (8)0.0035 (7)0.0007 (7)
C20.0289 (11)0.0356 (13)0.0332 (10)0.0046 (9)0.0079 (8)0.0003 (9)
C30.0256 (11)0.0554 (16)0.0419 (12)0.0031 (10)0.0121 (8)0.0028 (10)
C40.0415 (13)0.0435 (15)0.0383 (11)0.0144 (11)0.0118 (9)0.0039 (9)
C50.0475 (14)0.0274 (12)0.0436 (12)0.0043 (10)0.0115 (9)0.0007 (9)
C60.0315 (11)0.0313 (13)0.0358 (11)0.0045 (9)0.0077 (8)0.0012 (8)
C1A0.0253 (10)0.0304 (12)0.0245 (9)0.0036 (8)0.0040 (7)0.0000 (8)
C2A0.0295 (11)0.0423 (13)0.0257 (10)0.0012 (9)0.0034 (7)0.0049 (8)
C2A10.0490 (13)0.0451 (15)0.0287 (11)0.0069 (11)0.0001 (9)0.0079 (9)
C3A0.0405 (12)0.0528 (15)0.0245 (10)0.0018 (11)0.0005 (8)0.0006 (9)
C4A0.0474 (14)0.0509 (15)0.0274 (10)0.0073 (11)0.0069 (9)0.0105 (9)
C5A0.0386 (12)0.0350 (13)0.0345 (11)0.0049 (9)0.0115 (8)0.0037 (9)
C5A10.0645 (16)0.0398 (14)0.0476 (13)0.0036 (12)0.0160 (11)0.0071 (10)
C6A0.0309 (11)0.0352 (12)0.0271 (10)0.0019 (9)0.0061 (7)0.0011 (8)
Geometric parameters (Å, º) top
S1—O21.4381 (14)C1A—C2A1.411 (2)
S1—O11.4416 (13)C2A—C3A1.386 (3)
S1—C11.7624 (19)C2A—C2A11.505 (3)
S1—C1A1.7748 (18)C2A1—H2A10.9800
C1—C61.386 (3)C2A1—H2A20.9800
C1—C21.388 (3)C2A1—H2A30.9800
C2—C31.390 (3)C3A—C4A1.380 (3)
C2—H20.9500C3A—H3A0.9500
C3—C41.376 (3)C4A—C5A1.386 (3)
C3—H30.9500C4A—H4A0.9500
C4—C51.379 (3)C5A—C6A1.392 (3)
C4—H40.9500C5A—C5A11.500 (3)
C5—C61.384 (3)C5A1—H5A10.9800
C5—H50.9500C5A1—H5A20.9800
C6—H60.9500C5A1—H5A30.9800
C1A—C6A1.381 (3)C6A—H6A0.9500
O2—S1—O1117.69 (8)C3A—C2A—C1A115.31 (19)
O2—S1—C1108.46 (9)C3A—C2A—C2A1120.01 (17)
O1—S1—C1107.06 (8)C1A—C2A—C2A1124.67 (17)
O2—S1—C1A109.81 (8)C2A—C2A1—H2A1109.5
O1—S1—C1A107.19 (8)C2A—C2A1—H2A2109.5
C1—S1—C1A106.02 (8)H2A1—C2A1—H2A2109.5
C6—C1—C2121.20 (18)C2A—C2A1—H2A3109.5
C6—C1—S1119.75 (14)H2A1—C2A1—H2A3109.5
C2—C1—S1118.97 (15)H2A2—C2A1—H2A3109.5
C1—C2—C3118.8 (2)C4A—C3A—C2A122.70 (18)
C1—C2—H2120.6C4A—C3A—H3A118.6
C3—C2—H2120.6C2A—C3A—H3A118.6
C4—C3—C2120.2 (2)C3A—C4A—C5A121.57 (19)
C4—C3—H3119.9C3A—C4A—H4A119.2
C2—C3—H3119.9C5A—C4A—H4A119.2
C3—C4—C5120.4 (2)C4A—C5A—C6A117.0 (2)
C3—C4—H4119.8C4A—C5A—C5A1122.24 (19)
C5—C4—H4119.8C6A—C5A—C5A1120.80 (18)
C4—C5—C6120.4 (2)C5A—C5A1—H5A1109.5
C4—C5—H5119.8C5A—C5A1—H5A2109.5
C6—C5—H5119.8H5A1—C5A1—H5A2109.5
C5—C6—C1118.91 (19)C5A—C5A1—H5A3109.5
C5—C6—H6120.5H5A1—C5A1—H5A3109.5
C1—C6—H6120.5H5A2—C5A1—H5A3109.5
C6A—C1A—C2A122.22 (17)C1A—C6A—C5A121.23 (17)
C6A—C1A—S1116.76 (13)C1A—C6A—H6A119.4
C2A—C1A—S1121.01 (15)C5A—C6A—H6A119.4
O2—S1—C1—C61.42 (16)O2—S1—C1A—C2A48.49 (17)
O1—S1—C1—C6129.35 (14)O1—S1—C1A—C2A177.42 (14)
C1A—S1—C1—C6116.46 (14)C1—S1—C1A—C2A68.48 (17)
O2—S1—C1—C2175.52 (13)C6A—C1A—C2A—C3A0.1 (3)
O1—S1—C1—C247.58 (15)S1—C1A—C2A—C3A178.74 (15)
C1A—S1—C1—C266.61 (15)C6A—C1A—C2A—C2A1179.4 (2)
C6—C1—C2—C30.1 (3)S1—C1A—C2A—C2A11.8 (3)
S1—C1—C2—C3176.78 (14)C1A—C2A—C3A—C4A0.2 (3)
C1—C2—C3—C40.1 (3)C2A1—C2A—C3A—C4A179.7 (2)
C2—C3—C4—C50.5 (3)C2A—C3A—C4A—C5A0.2 (3)
C3—C4—C5—C60.9 (3)C3A—C4A—C5A—C6A0.0 (3)
C4—C5—C6—C10.8 (3)C3A—C4A—C5A—C5A1179.2 (2)
C2—C1—C6—C50.5 (3)C2A—C1A—C6A—C5A0.4 (3)
S1—C1—C6—C5176.41 (13)S1—C1A—C6A—C5A178.51 (15)
O2—S1—C1A—C6A130.43 (15)C4A—C5A—C6A—C1A0.4 (3)
O1—S1—C1A—C6A1.50 (17)C5A1—C5A—C6A—C1A178.88 (19)
C1—S1—C1A—C6A112.60 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.413.317 (3)161
C4—H4···O1ii0.952.553.392 (3)147
C6—H6···O1iii0.952.463.309 (3)149
Symmetry codes: (i) x1, y, z; (ii) x1/2, y1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2.

Experimental details

(1)(2)(3)(4)
Crystal data
Chemical formulaC14H14O2SC15H16O2SC12H9ClO2SC14H13ClO2S
Mr246.31260.34252.70280.75
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/nMonoclinic, P21/cMonoclinic, P21/n
Temperature (K)306150307150
a, b, c (Å)14.1773 (7), 7.7437 (4), 24.0161 (12)8.3374 (6), 14.9785 (8), 10.9064 (6)13.239 (3), 7.4521 (15), 11.737 (2)12.9682 (14), 7.5293 (12), 14.4627 (17)
β (°) 101.205 (1) 98.241 (3) 93.17 (3) 110.625 (7)
V3)2586.3 (2)1347.95 (14)1156.3 (4)1321.6 (3)
Z8444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.240.230.490.44
Crystal size (mm)0.56 × 0.18 × 0.130.2 × 0.2 × 0.030.40 × 0.28 × 0.240.10 × 0.08 × 0.05
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Kappa-CCD
diffractometer
Bruker SMART 1000 CCD
diffractometer
Kappa-CCD
diffractometer
Absorption correctionMulti-scan
SADABS (Bruker, 1997)
Multi-scan
SORTAV (Blessing, 1995 & 1997)
Multi-scan
SADABS (Bruker, 1997)
Multi-scan
SORTAV (Blessing, 1995 & 1997)
Tmin, Tmax0.879, 0.9700.929, 0.9690.828, 0.8910.958, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
15872, 4554, 2746 12210, 3060, 2172 7000, 2030, 1527 9255, 2545, 1332
Rint0.0230.0370.0200.053
(sin θ/λ)max1)0.5950.6470.5950.613
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.101, 0.93 0.047, 0.117, 1.04 0.039, 0.108, 1.04 0.059, 0.158, 0.93
No. of reflections4554306020302545
No. of parameters311166145165
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.230.24, 0.440.24, 0.400.34, 0.28


(5)
Crystal data
Chemical formulaC14H14O2S
Mr246.31
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)7.8879 (3), 10.9788 (4), 15.2489 (4)
β (°) 103.525 (2)
V3)1283.93 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.20 × 0.15 × 0.05
Data collection
DiffractometerKappa-CCD
diffractometer
Absorption correctionMulti-scan
SORTAV (Blessing, 1995 & 1997)
Tmin, Tmax0.954, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
14179, 2895, 1990
Rint0.038
(sin θ/λ)max1)0.646
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.122, 1.04
No. of reflections2895
No. of parameters156
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.42

Computer programs: SMART (Bruker, 1997), Kappa-CCD server software (Nonius, 1997), SAINT (Bruker, 1997), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b), ORTEP (Johnson, 1976), PLATON (Spek, 2000), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (1) top
D—H···AD—HH···AD···AD—H···A
C15A—H15A···O2Ai0.932.443.354 (3)166
C5B—H5B···O2Bi0.932.583.317 (3)137
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (2) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A···O2i0.932.433.292 (2)154
C2—H2···O2ii0.932.593.306 (2)134
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) for (3) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.583.500 (3)169
C5A—H5A···O1ii0.932.533.326 (4)143
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y1, z.
Hydrogen-bond geometry (Å, º) for (4) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.523.416 (5)158
C5A—H5A···O1ii0.952.453.319 (6)151
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x, y1, z.
Hydrogen-bond geometry (Å, º) for (5) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.413.317 (3)161
C4—H4···O1ii0.952.553.392 (3)147
C6—H6···O1iii0.952.463.309 (3)149
Symmetry codes: (i) x1, y, z; (ii) x1/2, y1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2.
 

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