In bis(4-tolyl) sulfone, C
14H
14O
2S (1), 2,5,4′-trimethyldiphenyl sulfone, C
15H
16O
2S (2), and 4-chlorodiphenyl sulfone, C
12H
9ClO
2S (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, C
14H
13ClO
2S (4), and 2,5-dimethyldiphenyl sulfone, C
14H
14O
2S (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
CCDC references: 163039; 163040; 163041; 163042; 163043
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).
(1) Bis-(4-tolyl) sulfone
top
Crystal data top
C14H14O2S | F(000) = 1040 |
Mr = 246.31 | Dx = 1.265 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.1773 (7) Å | Cell parameters from 15872 reflections |
b = 7.7437 (4) Å | θ = 1.5–25.0° |
c = 24.0161 (12) Å | µ = 0.24 mm−1 |
β = 101.205 (1)° | T = 306 K |
V = 2586.3 (2) Å3 | Needle, colourless |
Z = 8 | 0.56 × 0.18 × 0.13 mm |
Data collection top
Bruker SMART 1000 CCD diffractometer | 4554 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2746 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ scans and ω scans with κ offsets | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan SADABS (Bruker, 1997) | h = −16→16 |
Tmin = 0.879, Tmax = 0.970 | k = −9→9 |
15872 measured reflections | l = −28→22 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-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 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Crystal data top
C14H14O2S | V = 2586.3 (2) Å3 |
Mr = 246.31 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.1773 (7) Å | µ = 0.24 mm−1 |
b = 7.7437 (4) Å | T = 306 K |
c = 24.0161 (12) Å | 0.56 × 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 = 0.970 | Rint = 0.023 |
15872 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.14 e Å−3 |
4554 reflections | Δρmin = −0.23 e Å−3 |
311 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1A | 0.24013 (4) | 0.87124 (8) | 0.34337 (2) | 0.0686 (2) | |
O1A | 0.25425 (12) | 0.9434 (2) | 0.39953 (6) | 0.0899 (5) | |
O2A | 0.18549 (12) | 0.7149 (2) | 0.33154 (7) | 0.0961 (6) | |
C1A | 0.35449 (15) | 0.8367 (2) | 0.32655 (8) | 0.0560 (5) | |
C2A | 0.36334 (17) | 0.7421 (3) | 0.27882 (9) | 0.0700 (6) | |
C3A | 0.45260 (19) | 0.7146 (3) | 0.26651 (10) | 0.0771 (7) | |
C4A | 0.53513 (18) | 0.7763 (3) | 0.30085 (11) | 0.0721 (6) | |
C5A | 0.52521 (17) | 0.8694 (3) | 0.34834 (10) | 0.0753 (6) | |
C6A | 0.43592 (17) | 0.9014 (3) | 0.36107 (9) | 0.0680 (6) | |
C7A | 0.63242 (19) | 0.7456 (4) | 0.28665 (13) | 0.1132 (10) | |
C11A | 0.18541 (14) | 1.0286 (3) | 0.29492 (8) | 0.0570 (5) | |
C12A | 0.13688 (16) | 0.9823 (3) | 0.24176 (10) | 0.0751 (6) | |
C13A | 0.09612 (17) | 1.1078 (4) | 0.20416 (10) | 0.0857 (7) | |
C14A | 0.10220 (16) | 1.2799 (4) | 0.21773 (12) | 0.0777 (7) | |
C15A | 0.14976 (18) | 1.3238 (3) | 0.27114 (13) | 0.0844 (7) | |
C16A | 0.19170 (16) | 1.2002 (3) | 0.30968 (10) | 0.0723 (6) | |
C17A | 0.06006 (19) | 1.4165 (4) | 0.17519 (12) | 0.1185 (11) | |
S1B | 0.74507 (4) | 0.23084 (8) | 0.41418 (3) | 0.0735 (2) | |
O1B | 0.74717 (12) | 0.2700 (3) | 0.35586 (7) | 0.1049 (6) | |
O2B | 0.77506 (12) | 0.0630 (2) | 0.43635 (8) | 0.1018 (6) | |
C1B | 0.81210 (14) | 0.3885 (3) | 0.45778 (9) | 0.0593 (5) | |
C2B | 0.84830 (15) | 0.3531 (3) | 0.51413 (9) | 0.0684 (6) | |
C3B | 0.89424 (16) | 0.4822 (4) | 0.54840 (10) | 0.0797 (7) | |
C4B | 0.90558 (16) | 0.6456 (4) | 0.52858 (12) | 0.0770 (7) | |
C5B | 0.86955 (17) | 0.6772 (3) | 0.47183 (13) | 0.0852 (8) | |
C6B | 0.82273 (16) | 0.5516 (3) | 0.43639 (10) | 0.0754 (7) | |
C7B | 0.95345 (18) | 0.7873 (4) | 0.56691 (13) | 0.1202 (11) | |
C11B | 0.62691 (15) | 0.2657 (2) | 0.42496 (9) | 0.0571 (5) | |
C12B | 0.59972 (16) | 0.1994 (3) | 0.47255 (9) | 0.0671 (6) | |
C13B | 0.50825 (18) | 0.2346 (3) | 0.48208 (10) | 0.0746 (7) | |
C14B | 0.44386 (16) | 0.3347 (3) | 0.44516 (11) | 0.0702 (6) | |
C15B | 0.47337 (18) | 0.3979 (3) | 0.39775 (11) | 0.0787 (7) | |
C16B | 0.56384 (17) | 0.3651 (3) | 0.38758 (9) | 0.0717 (6) | |
C17B | 0.34563 (17) | 0.3725 (4) | 0.45697 (12) | 0.1095 (10) | |
H2A | 0.3089 | 0.6975 | 0.2552 | 0.084* | |
H3A | 0.4576 | 0.6526 | 0.2341 | 0.093* | |
H5A | 0.5798 | 0.9115 | 0.3723 | 0.090* | |
H6A | 0.4308 | 0.9665 | 0.3929 | 0.082* | |
H7A | 0.6804 | 0.8048 | 0.3136 | 0.170* | 0.50 |
H7B | 0.6330 | 0.7885 | 0.2492 | 0.170* | 0.50 |
H7C | 0.6460 | 0.6241 | 0.2880 | 0.170* | 0.50 |
H7D | 0.6258 | 0.6734 | 0.2536 | 0.170* | 0.50 |
H7E | 0.6733 | 0.6898 | 0.3180 | 0.170* | 0.50 |
H7F | 0.6603 | 0.8541 | 0.2792 | 0.170* | 0.50 |
H12A | 0.1316 | 0.8665 | 0.2313 | 0.090* | |
H13A | 0.0634 | 1.0749 | 0.1684 | 0.103* | |
H15A | 0.1539 | 1.4395 | 0.2817 | 0.101* | |
H16A | 0.2241 | 1.2332 | 0.3455 | 0.087* | |
H17A | −0.0061 | 1.3900 | 0.1602 | 0.178* | 0.50 |
H17B | 0.0952 | 1.4192 | 0.1448 | 0.178* | 0.50 |
H17C | 0.0644 | 1.5272 | 0.1935 | 0.178* | 0.50 |
H17D | 0.1084 | 1.5009 | 0.1722 | 0.178* | 0.50 |
H17E | 0.0071 | 1.4717 | 0.1875 | 0.178* | 0.50 |
H17F | 0.0379 | 1.3637 | 0.1388 | 0.178* | 0.50 |
H2B | 0.8418 | 0.2435 | 0.5288 | 0.082* | |
H3B | 0.9185 | 0.4579 | 0.5864 | 0.096* | |
H5B | 0.8772 | 0.7864 | 0.4572 | 0.102* | |
H6B | 0.7985 | 0.5761 | 0.3984 | 0.090* | |
H7G | 0.9216 | 0.8950 | 0.5560 | 0.180* | 0.50 |
H7H | 1.0197 | 0.7959 | 0.5637 | 0.180* | 0.50 |
H7I | 0.9495 | 0.7614 | 0.6055 | 0.180* | 0.50 |
H7J | 1.0056 | 0.7399 | 0.5941 | 0.180* | 0.50 |
H7K | 0.9075 | 0.8390 | 0.5864 | 0.180* | 0.50 |
H7L | 0.9778 | 0.8734 | 0.5446 | 0.180* | 0.50 |
H12B | 0.6421 | 0.1318 | 0.4980 | 0.081* | |
H13B | 0.4898 | 0.1896 | 0.5142 | 0.090* | |
H15B | 0.4311 | 0.4645 | 0.3720 | 0.094* | |
H16B | 0.5823 | 0.4102 | 0.3554 | 0.086* | |
H17G | 0.3089 | 0.4355 | 0.4257 | 0.164* | 0.50 |
H17H | 0.3517 | 0.4403 | 0.4909 | 0.164* | 0.50 |
H17I | 0.3136 | 0.2660 | 0.4618 | 0.164* | 0.50 |
H17J | 0.3406 | 0.3257 | 0.4933 | 0.164* | 0.50 |
H17K | 0.2977 | 0.3209 | 0.4280 | 0.164* | 0.50 |
H17L | 0.3359 | 0.4952 | 0.4571 | 0.164* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1A | 0.0796 (4) | 0.0687 (4) | 0.0612 (4) | 0.0042 (3) | 0.0231 (3) | 0.0082 (3) |
O1A | 0.1112 (13) | 0.1143 (13) | 0.0496 (9) | 0.0255 (11) | 0.0289 (9) | 0.0043 (9) |
O2A | 0.1017 (13) | 0.0698 (11) | 0.1225 (15) | −0.0168 (10) | 0.0358 (11) | 0.0152 (10) |
C1A | 0.0739 (14) | 0.0501 (12) | 0.0435 (12) | 0.0042 (11) | 0.0102 (10) | 0.0013 (9) |
C2A | 0.0789 (16) | 0.0730 (16) | 0.0551 (14) | 0.0049 (13) | 0.0058 (12) | −0.0085 (11) |
C3A | 0.100 (2) | 0.0760 (16) | 0.0593 (15) | 0.0166 (15) | 0.0241 (14) | −0.0057 (12) |
C4A | 0.0794 (17) | 0.0625 (15) | 0.0788 (17) | 0.0122 (13) | 0.0262 (14) | 0.0137 (13) |
C5A | 0.0709 (16) | 0.0708 (15) | 0.0810 (18) | −0.0044 (13) | 0.0067 (13) | −0.0015 (13) |
C6A | 0.0862 (17) | 0.0636 (14) | 0.0528 (13) | 0.0035 (13) | 0.0097 (12) | −0.0083 (11) |
C7A | 0.098 (2) | 0.112 (2) | 0.142 (3) | 0.0247 (18) | 0.0543 (19) | 0.0253 (19) |
C11A | 0.0580 (13) | 0.0613 (14) | 0.0536 (13) | −0.0005 (11) | 0.0159 (10) | −0.0014 (10) |
C12A | 0.0772 (16) | 0.0735 (16) | 0.0714 (16) | −0.0032 (13) | 0.0068 (13) | −0.0075 (13) |
C13A | 0.0736 (17) | 0.113 (2) | 0.0645 (16) | 0.0035 (16) | −0.0008 (12) | 0.0030 (16) |
C14A | 0.0589 (15) | 0.096 (2) | 0.0832 (19) | 0.0120 (15) | 0.0252 (13) | 0.0206 (16) |
C15A | 0.0910 (19) | 0.0606 (15) | 0.106 (2) | 0.0091 (14) | 0.0297 (16) | 0.0032 (15) |
C16A | 0.0803 (16) | 0.0708 (16) | 0.0649 (15) | 0.0017 (14) | 0.0117 (12) | −0.0064 (13) |
C17A | 0.097 (2) | 0.136 (2) | 0.128 (2) | 0.0353 (19) | 0.0335 (18) | 0.063 (2) |
S1B | 0.0729 (4) | 0.0802 (4) | 0.0698 (4) | 0.0102 (3) | 0.0202 (3) | −0.0138 (3) |
O1B | 0.1013 (13) | 0.1600 (17) | 0.0595 (11) | −0.0036 (12) | 0.0309 (9) | −0.0240 (11) |
O2B | 0.0973 (13) | 0.0651 (11) | 0.1415 (16) | 0.0257 (10) | 0.0194 (11) | −0.0157 (10) |
C1B | 0.0535 (12) | 0.0682 (14) | 0.0586 (14) | 0.0127 (11) | 0.0169 (10) | 0.0013 (11) |
C2B | 0.0614 (14) | 0.0751 (16) | 0.0678 (16) | 0.0090 (12) | 0.0103 (12) | 0.0079 (13) |
C3B | 0.0613 (15) | 0.111 (2) | 0.0651 (16) | 0.0083 (15) | 0.0084 (12) | −0.0030 (16) |
C4B | 0.0513 (14) | 0.092 (2) | 0.092 (2) | 0.0059 (14) | 0.0238 (13) | −0.0174 (16) |
C5B | 0.0775 (17) | 0.0658 (16) | 0.119 (2) | 0.0028 (14) | 0.0361 (17) | 0.0027 (16) |
C6B | 0.0769 (16) | 0.0823 (18) | 0.0692 (16) | 0.0080 (14) | 0.0193 (13) | 0.0114 (14) |
C7B | 0.0811 (19) | 0.129 (2) | 0.155 (3) | −0.0177 (19) | 0.0337 (18) | −0.068 (2) |
C11B | 0.0636 (13) | 0.0544 (12) | 0.0522 (13) | 0.0016 (11) | 0.0090 (10) | −0.0070 (10) |
C12B | 0.0705 (15) | 0.0704 (14) | 0.0578 (14) | 0.0034 (12) | 0.0058 (12) | 0.0027 (11) |
C13B | 0.0785 (16) | 0.0890 (17) | 0.0587 (15) | −0.0159 (15) | 0.0193 (13) | −0.0084 (13) |
C14B | 0.0617 (15) | 0.0698 (15) | 0.0782 (17) | −0.0034 (13) | 0.0110 (13) | −0.0303 (13) |
C15B | 0.0767 (17) | 0.0705 (16) | 0.0834 (18) | 0.0169 (13) | 0.0024 (14) | 0.0009 (14) |
C16B | 0.0790 (17) | 0.0712 (15) | 0.0651 (15) | 0.0076 (13) | 0.0145 (13) | 0.0099 (12) |
C17B | 0.0718 (17) | 0.126 (2) | 0.134 (3) | −0.0052 (16) | 0.0285 (16) | −0.060 (2) |
Geometric parameters (Å, º) top
S1A—O2A | 1.4357 (16) | S1B—O2B | 1.4372 (16) |
S1A—O1A | 1.4378 (15) | S1B—O1B | 1.4392 (17) |
S1A—C11A | 1.758 (2) | S1B—C1B | 1.761 (2) |
S1A—C1A | 1.766 (2) | S1B—C11B | 1.765 (2) |
C1A—C6A | 1.378 (3) | C1B—C2B | 1.378 (3) |
C1A—C2A | 1.387 (3) | C1B—C6B | 1.383 (3) |
C2A—C3A | 1.371 (3) | C2B—C3B | 1.376 (3) |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.379 (3) | C3B—C4B | 1.372 (3) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.379 (3) | C4B—C5B | 1.381 (3) |
C4A—C7A | 1.503 (3) | C4B—C7B | 1.506 (3) |
C5A—C6A | 1.381 (3) | C5B—C6B | 1.375 (3) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—H7A | 0.9600 | C7B—H7G | 0.9600 |
C7A—H7B | 0.9600 | C7B—H7H | 0.9600 |
C7A—H7C | 0.9600 | C7B—H7I | 0.9600 |
C7A—H7D | 0.9600 | C7B—H7J | 0.9600 |
C7A—H7E | 0.9600 | C7B—H7K | 0.9600 |
C7A—H7F | 0.9600 | C7B—H7L | 0.9600 |
C11A—C16A | 1.374 (3) | C11B—C16B | 1.373 (3) |
C11A—C12A | 1.375 (3) | C11B—C12B | 1.375 (3) |
C12A—C13A | 1.376 (3) | C12B—C13B | 1.387 (3) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—C14A | 1.370 (3) | C13B—C14B | 1.381 (3) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.371 (3) | C14B—C15B | 1.377 (3) |
C14A—C17A | 1.511 (3) | C14B—C17B | 1.503 (3) |
C15A—C16A | 1.383 (3) | C15B—C16B | 1.375 (3) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—H17A | 0.9600 | C17B—H17G | 0.9600 |
C17A—H17B | 0.9600 | C17B—H17H | 0.9600 |
C17A—H17C | 0.9600 | C17B—H17I | 0.9600 |
C17A—H17D | 0.9600 | C17B—H17J | 0.9600 |
C17A—H17E | 0.9600 | C17B—H17K | 0.9600 |
C17A—H17F | 0.9600 | C17B—H17L | 0.9600 |
| | | |
O2A—S1A—O1A | 119.00 (10) | O2B—S1B—O1B | 119.38 (11) |
O2A—S1A—C11A | 107.57 (10) | O2B—S1B—C1B | 108.66 (10) |
O1A—S1A—C11A | 108.34 (10) | O1B—S1B—C1B | 108.77 (11) |
O2A—S1A—C1A | 108.14 (10) | O2B—S1B—C11B | 107.76 (10) |
O1A—S1A—C1A | 107.86 (10) | O1B—S1B—C11B | 108.07 (10) |
C11A—S1A—C1A | 105.09 (9) | C1B—S1B—C11B | 102.98 (9) |
C6A—C1A—C2A | 119.3 (2) | C2B—C1B—C6B | 120.0 (2) |
C6A—C1A—S1A | 120.44 (16) | C2B—C1B—S1B | 120.06 (18) |
C2A—C1A—S1A | 120.24 (17) | C6B—C1B—S1B | 119.82 (18) |
C3A—C2A—C1A | 119.7 (2) | C3B—C2B—C1B | 119.0 (2) |
C3A—C2A—H2A | 120.1 | C3B—C2B—H2B | 120.5 |
C1A—C2A—H2A | 120.1 | C1B—C2B—H2B | 120.5 |
C2A—C3A—C4A | 121.9 (2) | C4B—C3B—C2B | 122.4 (2) |
C2A—C3A—H3A | 119.0 | C4B—C3B—H3B | 118.8 |
C4A—C3A—H3A | 119.0 | C2B—C3B—H3B | 118.8 |
C3A—C4A—C5A | 117.7 (2) | C3B—C4B—C5B | 117.4 (2) |
C3A—C4A—C7A | 121.3 (2) | C3B—C4B—C7B | 121.9 (3) |
C5A—C4A—C7A | 121.1 (2) | C5B—C4B—C7B | 120.7 (3) |
C4A—C5A—C6A | 121.5 (2) | C6B—C5B—C4B | 121.8 (2) |
C4A—C5A—H5A | 119.3 | C6B—C5B—H5B | 119.1 |
C6A—C5A—H5A | 119.3 | C4B—C5B—H5B | 119.1 |
C1A—C6A—C5A | 119.9 (2) | C5B—C6B—C1B | 119.4 (2) |
C1A—C6A—H6A | 120.1 | C5B—C6B—H6B | 120.3 |
C5A—C6A—H6A | 120.1 | C1B—C6B—H6B | 120.3 |
C4A—C7A—H7A | 109.5 | C4B—C7B—H7G | 109.5 |
C4A—C7A—H7B | 109.5 | C4B—C7B—H7H | 109.5 |
H7A—C7A—H7B | 109.5 | H7G—C7B—H7H | 109.5 |
C4A—C7A—H7C | 109.5 | C4B—C7B—H7I | 109.5 |
H7A—C7A—H7C | 109.5 | H7G—C7B—H7I | 109.5 |
H7B—C7A—H7C | 109.5 | H7H—C7B—H7I | 109.5 |
C4A—C7A—H7D | 109.5 | C4B—C7B—H7J | 109.5 |
H7A—C7A—H7D | 141.1 | H7G—C7B—H7J | 141.1 |
H7B—C7A—H7D | 56.3 | H7H—C7B—H7J | 56.3 |
H7C—C7A—H7D | 56.3 | H7I—C7B—H7J | 56.3 |
C4A—C7A—H7E | 109.5 | C4B—C7B—H7K | 109.5 |
H7A—C7A—H7E | 56.3 | H7G—C7B—H7K | 56.3 |
H7B—C7A—H7E | 141.1 | H7H—C7B—H7K | 141.1 |
H7C—C7A—H7E | 56.3 | H7I—C7B—H7K | 56.3 |
H7D—C7A—H7E | 109.5 | H7J—C7B—H7K | 109.5 |
C4A—C7A—H7F | 109.5 | C4B—C7B—H7L | 109.5 |
H7A—C7A—H7F | 56.3 | H7G—C7B—H7L | 56.3 |
H7B—C7A—H7F | 56.3 | H7H—C7B—H7L | 56.3 |
H7C—C7A—H7F | 141.1 | H7I—C7B—H7L | 141.1 |
H7D—C7A—H7F | 109.5 | H7J—C7B—H7L | 109.5 |
H7E—C7A—H7F | 109.5 | H7K—C7B—H7L | 109.5 |
C16A—C11A—C12A | 119.2 (2) | C16B—C11B—C12B | 120.0 (2) |
C16A—C11A—S1A | 120.11 (17) | C16B—C11B—S1B | 120.39 (17) |
C12A—C11A—S1A | 120.71 (18) | C12B—C11B—S1B | 119.49 (17) |
C11A—C12A—C13A | 119.7 (2) | C11B—C12B—C13B | 119.1 (2) |
C11A—C12A—H12A | 120.1 | C11B—C12B—H12B | 120.5 |
C13A—C12A—H12A | 120.1 | C13B—C12B—H12B | 120.5 |
C14A—C13A—C12A | 122.1 (2) | C14B—C13B—C12B | 121.8 (2) |
C14A—C13A—H13A | 118.9 | C14B—C13B—H13B | 119.1 |
C12A—C13A—H13A | 118.9 | C12B—C13B—H13B | 119.1 |
C13A—C14A—C15A | 117.4 (2) | C15B—C14B—C13B | 117.5 (2) |
C13A—C14A—C17A | 121.4 (3) | C15B—C14B—C17B | 121.9 (2) |
C15A—C14A—C17A | 121.1 (3) | C13B—C14B—C17B | 120.6 (2) |
C14A—C15A—C16A | 121.6 (2) | C16B—C15B—C14B | 121.7 (2) |
C14A—C15A—H15A | 119.2 | C16B—C15B—H15B | 119.2 |
C16A—C15A—H15A | 119.2 | C14B—C15B—H15B | 119.2 |
C11A—C16A—C15A | 119.9 (2) | C11B—C16B—C15B | 119.9 (2) |
C11A—C16A—H16A | 120.0 | C11B—C16B—H16B | 120.0 |
C15A—C16A—H16A | 120.0 | C15B—C16B—H16B | 120.0 |
C14A—C17A—H17A | 109.5 | C14B—C17B—H17G | 109.5 |
C14A—C17A—H17B | 109.5 | C14B—C17B—H17H | 109.5 |
H17A—C17A—H17B | 109.5 | H17G—C17B—H17H | 109.5 |
C14A—C17A—H17C | 109.5 | C14B—C17B—H17I | 109.5 |
H17A—C17A—H17C | 109.5 | H17G—C17B—H17I | 109.5 |
H17B—C17A—H17C | 109.5 | H17H—C17B—H17I | 109.5 |
C14A—C17A—H17D | 109.5 | C14B—C17B—H17J | 109.5 |
H17A—C17A—H17D | 141.1 | H17G—C17B—H17J | 141.1 |
H17B—C17A—H17D | 56.3 | H17H—C17B—H17J | 56.3 |
H17C—C17A—H17D | 56.3 | H17I—C17B—H17J | 56.3 |
C14A—C17A—H17E | 109.5 | C14B—C17B—H17K | 109.5 |
H17A—C17A—H17E | 56.3 | H17G—C17B—H17K | 56.3 |
H17B—C17A—H17E | 141.1 | H17H—C17B—H17K | 141.1 |
H17C—C17A—H17E | 56.3 | H17I—C17B—H17K | 56.3 |
H17D—C17A—H17E | 109.5 | H17J—C17B—H17K | 109.5 |
C14A—C17A—H17F | 109.5 | C14B—C17B—H17L | 109.5 |
H17A—C17A—H17F | 56.3 | H17G—C17B—H17L | 56.3 |
H17B—C17A—H17F | 56.3 | H17H—C17B—H17L | 56.3 |
H17C—C17A—H17F | 141.1 | H17I—C17B—H17L | 141.1 |
H17D—C17A—H17F | 109.5 | H17J—C17B—H17L | 109.5 |
H17E—C17A—H17F | 109.5 | H17K—C17B—H17L | 109.5 |
| | | |
O2A—S1A—C1A—C6A | −139.65 (17) | O2B—S1B—C1B—C2B | −27.01 (19) |
O1A—S1A—C1A—C6A | −9.7 (2) | O1B—S1B—C1B—C2B | −158.44 (17) |
C11A—S1A—C1A—C6A | 105.68 (18) | C11B—S1B—C1B—C2B | 87.08 (18) |
O2A—S1A—C1A—C2A | 39.45 (19) | O2B—S1B—C1B—C6B | 157.39 (17) |
O1A—S1A—C1A—C2A | 169.37 (16) | O1B—S1B—C1B—C6B | 26.0 (2) |
C11A—S1A—C1A—C2A | −75.22 (18) | C11B—S1B—C1B—C6B | −88.52 (18) |
C6A—C1A—C2A—C3A | −0.2 (3) | C6B—C1B—C2B—C3B | 0.4 (3) |
S1A—C1A—C2A—C3A | −179.32 (17) | S1B—C1B—C2B—C3B | −175.19 (16) |
C1A—C2A—C3A—C4A | 1.0 (3) | C1B—C2B—C3B—C4B | −0.1 (3) |
C2A—C3A—C4A—C5A | −0.7 (3) | C2B—C3B—C4B—C5B | −0.6 (3) |
C2A—C3A—C4A—C7A | −179.8 (2) | C2B—C3B—C4B—C7B | 178.2 (2) |
C3A—C4A—C5A—C6A | −0.5 (3) | C3B—C4B—C5B—C6B | 1.0 (3) |
C7A—C4A—C5A—C6A | 178.6 (2) | C7B—C4B—C5B—C6B | −177.8 (2) |
C2A—C1A—C6A—C5A | −1.0 (3) | C4B—C5B—C6B—C1B | −0.7 (3) |
S1A—C1A—C6A—C5A | 178.16 (16) | C2B—C1B—C6B—C5B | 0.0 (3) |
C4A—C5A—C6A—C1A | 1.3 (3) | S1B—C1B—C6B—C5B | 175.57 (16) |
O2A—S1A—C11A—C16A | 150.93 (17) | O2B—S1B—C11B—C16B | −148.83 (17) |
O1A—S1A—C11A—C16A | 21.1 (2) | O1B—S1B—C11B—C16B | −18.6 (2) |
C1A—S1A—C11A—C16A | −94.00 (18) | C1B—S1B—C11B—C16B | 96.43 (18) |
O2A—S1A—C11A—C12A | −29.8 (2) | O2B—S1B—C11B—C12B | 34.23 (19) |
O1A—S1A—C11A—C12A | −159.66 (17) | O1B—S1B—C11B—C12B | 164.49 (16) |
C1A—S1A—C11A—C12A | 85.25 (19) | C1B—S1B—C11B—C12B | −80.52 (18) |
C16A—C11A—C12A—C13A | 0.5 (3) | C16B—C11B—C12B—C13B | −0.1 (3) |
S1A—C11A—C12A—C13A | −178.80 (17) | S1B—C11B—C12B—C13B | 176.85 (16) |
C11A—C12A—C13A—C14A | 0.1 (4) | C11B—C12B—C13B—C14B | −0.1 (3) |
C12A—C13A—C14A—C15A | −0.9 (4) | C12B—C13B—C14B—C15B | 0.6 (3) |
C12A—C13A—C14A—C17A | 177.8 (2) | C12B—C13B—C14B—C17B | −179.2 (2) |
C13A—C14A—C15A—C16A | 1.2 (4) | C13B—C14B—C15B—C16B | −0.8 (3) |
C17A—C14A—C15A—C16A | −177.5 (2) | C17B—C14B—C15B—C16B | 179.0 (2) |
C12A—C11A—C16A—C15A | −0.2 (3) | C12B—C11B—C16B—C15B | −0.1 (3) |
S1A—C11A—C16A—C15A | 179.04 (17) | S1B—C11B—C16B—C15B | −177.06 (17) |
C14A—C15A—C16A—C11A | −0.6 (4) | C14B—C15B—C16B—C11B | 0.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15A—H15A···O2Ai | 0.93 | 2.44 | 3.354 (3) | 166 |
C5B—H5B···O2Bi | 0.93 | 2.58 | 3.317 (3) | 137 |
Symmetry code: (i) x, y+1, z. |
(2) 2,5,4'-Trimethyldiphenyl sulfone
top
Crystal data top
C15H16O2S | F(000) = 552 |
Mr = 260.34 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3374 (6) Å | Cell parameters from 12210 reflections |
b = 14.9785 (8) Å | θ = 2.3–27.4° |
c = 10.9064 (6) Å | µ = 0.23 mm−1 |
β = 98.241 (3)° | T = 150 K |
V = 1347.95 (14) Å3 | Plate, colourless |
Z = 4 | 0.2 × 0.2 × 0.03 mm |
Data collection top
Kappa-CCD diffractometer | 3060 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2172 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ϕ scans and ω scans with κ offsets | θmax = 27.4°, θmin = 2.3° |
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997) | h = −10→10 |
Tmin = 0.929, Tmax = 0.969 | k = −18→19 |
12210 measured reflections | l = −14→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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
Crystal data top
C15H16O2S | V = 1347.95 (14) Å3 |
Mr = 260.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.3374 (6) Å | µ = 0.23 mm−1 |
b = 14.9785 (8) Å | T = 150 K |
c = 10.9064 (6) Å | 0.2 × 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 = 0.969 | Rint = 0.037 |
12210 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.24 e Å−3 |
3060 reflections | Δρmin = −0.44 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.46216 (6) | 0.31838 (3) | 0.09163 (4) | 0.02781 (17) | |
O1 | 0.49354 (17) | 0.22681 (8) | 0.12618 (13) | 0.0369 (4) | |
O2 | 0.53037 (16) | 0.35246 (9) | −0.01306 (12) | 0.0342 (3) | |
C1 | 0.5347 (2) | 0.38672 (12) | 0.21938 (16) | 0.0267 (4) | |
C2 | 0.5118 (2) | 0.47859 (12) | 0.21014 (17) | 0.0300 (4) | |
H2 | 0.4504 | 0.5031 | 0.1403 | 0.036* | |
C3 | 0.5803 (2) | 0.53284 (13) | 0.30477 (18) | 0.0336 (5) | |
H3 | 0.5637 | 0.5942 | 0.2985 | 0.040* | |
C4 | 0.6744 (2) | 0.49798 (13) | 0.41049 (17) | 0.0331 (5) | |
C41 | 0.7522 (3) | 0.55939 (15) | 0.51092 (19) | 0.0470 (6) | |
H14 | 0.6762 | 0.5728 | 0.5666 | 0.071* | |
H24 | 0.7844 | 0.6137 | 0.4745 | 0.071* | |
H34 | 0.8458 | 0.5309 | 0.5558 | 0.071* | |
C5 | 0.6946 (3) | 0.40644 (14) | 0.41791 (18) | 0.0383 (5) | |
H5 | 0.7566 | 0.3820 | 0.4875 | 0.046* | |
C6 | 0.6248 (3) | 0.35026 (13) | 0.32433 (18) | 0.0348 (5) | |
H6 | 0.6381 | 0.2888 | 0.3317 | 0.042* | |
C1A | 0.2503 (2) | 0.33652 (11) | 0.05977 (16) | 0.0248 (4) | |
C2A | 0.1421 (2) | 0.30131 (12) | 0.13526 (17) | 0.0292 (4) | |
C21A | 0.19468 (18) | 0.24921 (13) | 0.25158 (15) | 0.0376 (5) | |
H12A | 0.1090 | 0.2488 | 0.3017 | 0.056* | |
H22A | 0.2893 | 0.2764 | 0.2969 | 0.056* | |
H32A | 0.2194 | 0.1890 | 0.2306 | 0.056* | |
C3A | −0.02068 (18) | 0.31750 (12) | 0.09638 (14) | 0.0337 (5) | |
H3A | −0.0964 | 0.2948 | 0.1430 | 0.040* | |
C4A | −0.0749 (2) | 0.36618 (13) | −0.00909 (18) | 0.0342 (5) | |
H4A | −0.1856 | 0.3750 | −0.0317 | 0.041* | |
C5A | 0.0323 (2) | 0.40230 (12) | −0.08212 (17) | 0.0290 (4) | |
C51A | −0.0249 (3) | 0.45567 (14) | −0.19734 (18) | 0.0373 (5) | |
H15A | 0.0547 | 0.5001 | −0.2087 | 0.056* | |
H25A | −0.1257 | 0.4844 | −0.1889 | 0.056* | |
H35A | −0.0401 | 0.4166 | −0.2678 | 0.056* | |
C6A | 0.1956 (2) | 0.38638 (12) | −0.04544 (16) | 0.0274 (4) | |
H6A | 0.2706 | 0.4096 | −0.0923 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0264 (3) | 0.0284 (3) | 0.0290 (3) | 0.00289 (19) | 0.0052 (2) | 0.0013 (2) |
O1 | 0.0396 (9) | 0.0261 (7) | 0.0440 (8) | 0.0065 (6) | 0.0024 (7) | 0.0003 (6) |
O2 | 0.0275 (8) | 0.0470 (9) | 0.0301 (7) | 0.0032 (6) | 0.0108 (6) | 0.0046 (6) |
C1 | 0.0244 (10) | 0.0288 (10) | 0.0276 (10) | 0.0010 (8) | 0.0065 (8) | 0.0039 (8) |
C2 | 0.0279 (11) | 0.0310 (10) | 0.0305 (10) | 0.0007 (8) | 0.0023 (8) | 0.0066 (8) |
C3 | 0.0371 (12) | 0.0267 (10) | 0.0371 (11) | −0.0019 (9) | 0.0060 (9) | 0.0031 (9) |
C4 | 0.0312 (11) | 0.0379 (11) | 0.0303 (10) | −0.0065 (9) | 0.0044 (9) | 0.0018 (9) |
C41 | 0.0509 (15) | 0.0494 (14) | 0.0386 (12) | −0.0123 (11) | −0.0011 (11) | −0.0022 (10) |
C5 | 0.0406 (13) | 0.0393 (12) | 0.0320 (11) | −0.0013 (10) | −0.0049 (9) | 0.0107 (9) |
C6 | 0.0404 (13) | 0.0279 (10) | 0.0346 (11) | 0.0011 (9) | 0.0002 (9) | 0.0079 (9) |
C1A | 0.0245 (10) | 0.0246 (9) | 0.0254 (9) | −0.0012 (7) | 0.0041 (8) | −0.0036 (7) |
C2A | 0.0321 (11) | 0.0253 (9) | 0.0306 (10) | −0.0050 (8) | 0.0067 (8) | −0.0039 (8) |
C21A | 0.0412 (13) | 0.0401 (11) | 0.0326 (11) | −0.0068 (10) | 0.0089 (9) | 0.0053 (9) |
C3A | 0.0305 (12) | 0.0355 (11) | 0.0371 (11) | −0.0084 (9) | 0.0118 (9) | −0.0056 (9) |
C4A | 0.0241 (11) | 0.0360 (11) | 0.0412 (12) | −0.0005 (9) | 0.0008 (9) | −0.0092 (9) |
C5A | 0.0307 (11) | 0.0249 (10) | 0.0304 (10) | 0.0020 (8) | 0.0011 (8) | −0.0072 (8) |
C51A | 0.0395 (13) | 0.0343 (11) | 0.0353 (11) | 0.0037 (9) | −0.0046 (9) | −0.0025 (9) |
C6A | 0.0289 (11) | 0.0250 (9) | 0.0285 (10) | −0.0014 (8) | 0.0050 (8) | −0.0031 (8) |
Geometric parameters (Å, º) top
S1—O1 | 1.4363 (13) | C1A—C6A | 1.390 (3) |
S1—O2 | 1.4400 (13) | C1A—C2A | 1.408 (2) |
S1—C1 | 1.7644 (19) | C2A—C3A | 1.384 (2) |
S1—C1A | 1.7716 (19) | C2A—C21A | 1.500 (2) |
C1—C6 | 1.388 (3) | C21A—H12A | 0.9600 |
C1—C2 | 1.391 (3) | C21A—H22A | 0.9600 |
C2—C3 | 1.372 (3) | C21A—H32A | 0.9600 |
C2—H2 | 0.9300 | C3A—C4A | 1.382 (2) |
C3—C4 | 1.399 (3) | C3A—H3A | 0.9300 |
C3—H3 | 0.9300 | C4A—C5A | 1.389 (3) |
C4—C5 | 1.382 (3) | C4A—H4A | 0.9300 |
C4—C41 | 1.505 (3) | C5A—C6A | 1.384 (3) |
C41—H14 | 0.9600 | C5A—C51A | 1.508 (3) |
C41—H24 | 0.9600 | C51A—H15A | 0.9600 |
C41—H34 | 0.9600 | C51A—H25A | 0.9600 |
C5—C6 | 1.385 (3) | C51A—H35A | 0.9600 |
C5—H5 | 0.9300 | C6A—H6A | 0.9300 |
C6—H6 | 0.9300 | | |
| | | |
O1—S1—O2 | 117.95 (8) | C6A—C1A—C2A | 121.48 (18) |
O1—S1—C1 | 108.53 (8) | C6A—C1A—S1 | 116.37 (13) |
O2—S1—C1 | 106.91 (8) | C2A—C1A—S1 | 122.15 (14) |
O1—S1—C1A | 109.69 (8) | C3A—C2A—C1A | 115.94 (16) |
O2—S1—C1A | 106.62 (8) | C3A—C2A—C21A | 120.33 (15) |
C1—S1—C1A | 106.56 (8) | C1A—C2A—C21A | 123.73 (17) |
C6—C1—C2 | 120.10 (18) | C2A—C21A—H12A | 109.5 |
C6—C1—S1 | 120.45 (15) | C2A—C21A—H22A | 109.5 |
C2—C1—S1 | 119.26 (14) | H12A—C21A—H22A | 109.5 |
C3—C2—C1 | 119.56 (18) | C2A—C21A—H32A | 109.5 |
C3—C2—H2 | 120.2 | H12A—C21A—H32A | 109.5 |
C1—C2—H2 | 120.2 | H22A—C21A—H32A | 109.5 |
C2—C3—C4 | 121.50 (18) | C4A—C3A—C2A | 122.47 (14) |
C2—C3—H3 | 119.2 | C4A—C3A—H3A | 118.8 |
C4—C3—H3 | 119.2 | C2A—C3A—H3A | 118.8 |
C5—C4—C3 | 117.88 (18) | C3A—C4A—C5A | 121.48 (18) |
C5—C4—C41 | 121.84 (18) | C3A—C4A—H4A | 119.3 |
C3—C4—C41 | 120.28 (18) | C5A—C4A—H4A | 119.3 |
C4—C41—H14 | 109.5 | C6A—C5A—C4A | 117.02 (18) |
C4—C41—H24 | 109.5 | C6A—C5A—C51A | 120.83 (17) |
H14—C41—H24 | 109.5 | C4A—C5A—C51A | 122.14 (18) |
C4—C41—H34 | 109.5 | C5A—C51A—H15A | 109.5 |
H14—C41—H34 | 109.5 | C5A—C51A—H25A | 109.5 |
H24—C41—H34 | 109.5 | H15A—C51A—H25A | 109.5 |
C4—C5—C6 | 121.64 (18) | C5A—C51A—H35A | 109.5 |
C4—C5—H5 | 119.2 | H15A—C51A—H35A | 109.5 |
C6—C5—H5 | 119.2 | H25A—C51A—H35A | 109.5 |
C5—C6—C1 | 119.30 (18) | C5A—C6A—C1A | 121.59 (17) |
C5—C6—H6 | 120.4 | C5A—C6A—H6A | 119.2 |
C1—C6—H6 | 120.4 | C1A—C6A—H6A | 119.2 |
| | | |
O1—S1—C1—C6 | 7.81 (18) | C1—S1—C1A—C6A | 106.81 (14) |
O2—S1—C1—C6 | −120.40 (16) | O1—S1—C1A—C2A | 43.05 (17) |
C1A—S1—C1—C6 | 125.87 (16) | O2—S1—C1A—C2A | 171.83 (14) |
O1—S1—C1—C2 | −177.27 (14) | C1—S1—C1A—C2A | −74.25 (16) |
O2—S1—C1—C2 | 54.51 (16) | C6A—C1A—C2A—C3A | 1.6 (3) |
C1A—S1—C1—C2 | −59.21 (16) | S1—C1A—C2A—C3A | −177.30 (13) |
C6—C1—C2—C3 | 0.7 (3) | C6A—C1A—C2A—C21A | −178.28 (17) |
S1—C1—C2—C3 | −174.23 (14) | S1—C1A—C2A—C21A | 2.8 (3) |
C1—C2—C3—C4 | 0.6 (3) | C1A—C2A—C3A—C4A | −0.8 (3) |
C2—C3—C4—C5 | −1.0 (3) | C21A—C2A—C3A—C4A | 179.07 (17) |
C2—C3—C4—C41 | 178.06 (18) | C2A—C3A—C4A—C5A | −0.4 (3) |
C3—C4—C5—C6 | 0.1 (3) | C3A—C4A—C5A—C6A | 0.8 (3) |
C41—C4—C5—C6 | −178.95 (19) | C3A—C4A—C5A—C51A | −179.91 (17) |
C4—C5—C6—C1 | 1.2 (3) | C4A—C5A—C6A—C1A | 0.0 (3) |
C2—C1—C6—C5 | −1.6 (3) | C51A—C5A—C6A—C1A | −179.30 (16) |
S1—C1—C6—C5 | 173.29 (15) | C2A—C1A—C6A—C5A | −1.2 (3) |
O1—S1—C1A—C6A | −135.89 (14) | S1—C1A—C6A—C5A | 177.74 (14) |
O2—S1—C1A—C6A | −7.11 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4A—H4A···O2i | 0.93 | 2.43 | 3.292 (2) | 154 |
C2—H2···O2ii | 0.93 | 2.59 | 3.306 (2) | 134 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z. |
(3) 4-Chlorodiphenyl sulfone
top
Crystal data top
C12H9ClO2S | F(000) = 520 |
Mr = 252.70 | Dx = 1.452 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.239 (3) Å | Cell parameters from 3848 reflections |
b = 7.4521 (15) Å | θ = 1.5–25.0° |
c = 11.737 (2) Å | µ = 0.49 mm−1 |
β = 93.17 (3)° | T = 307 K |
V = 1156.3 (4) Å3 | Block, yellow |
Z = 4 | 0.40 × 0.28 × 0.24 mm |
Data collection top
Bruker SMART 1000 CCD diffractometer | 2030 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1527 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ϕ scans and ω scans with κ offsets | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan SADABS (Bruker, 1997) | h = −15→15 |
Tmin = 0.828, Tmax = 0.891 | k = −8→8 |
7000 measured reflections | l = −8→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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Crystal data top
C12H9ClO2S | V = 1156.3 (4) Å3 |
Mr = 252.70 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.239 (3) Å | µ = 0.49 mm−1 |
b = 7.4521 (15) Å | T = 307 K |
c = 11.737 (2) Å | 0.40 × 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 = 0.891 | Rint = 0.020 |
7000 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.24 e Å−3 |
2030 reflections | Δρmin = −0.40 e Å−3 |
145 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.22766 (5) | 0.17244 (9) | 0.31273 (5) | 0.0624 (2) | |
O1 | 0.26580 (14) | 0.3492 (3) | 0.3348 (2) | 0.0916 (7) | |
O2 | 0.22962 (14) | 0.0990 (3) | 0.19946 (14) | 0.0889 (7) | |
C1 | 0.10107 (16) | 0.1681 (3) | 0.35280 (17) | 0.0464 (5) | |
C2 | 0.02900 (17) | 0.0831 (3) | 0.28305 (19) | 0.0549 (6) | |
C3 | −0.07109 (18) | 0.0891 (3) | 0.3102 (2) | 0.0627 (6) | |
C4 | −0.09809 (19) | 0.1760 (3) | 0.4071 (2) | 0.0618 (6) | |
C5 | −0.0253 (2) | 0.2571 (4) | 0.4773 (2) | 0.0639 (7) | |
C6 | 0.07406 (18) | 0.2552 (3) | 0.45115 (19) | 0.0580 (6) | |
C1A | 0.29383 (16) | 0.0241 (3) | 0.40809 (18) | 0.0520 (6) | |
C2A | 0.33534 (19) | 0.0875 (4) | 0.5104 (2) | 0.0659 (7) | |
C3A | 0.38710 (19) | −0.0305 (5) | 0.5835 (2) | 0.0762 (8) | |
C4A | 0.39620 (18) | −0.2070 (4) | 0.5527 (2) | 0.0680 (7) | |
Cl4A | 0.46364 (7) | −0.35274 (15) | 0.64329 (8) | 0.1160 (4) | |
C5A | 0.35342 (19) | −0.2712 (4) | 0.4519 (2) | 0.0691 (7) | |
C6A | 0.30174 (18) | −0.1543 (3) | 0.3793 (2) | 0.0613 (6) | |
H2 | 0.0476 | 0.0223 | 0.2183 | 0.066* | |
H3 | −0.1204 | 0.0341 | 0.2626 | 0.075* | |
H4 | −0.1656 | 0.1800 | 0.4251 | 0.074* | |
H5 | −0.0438 | 0.3141 | 0.5435 | 0.077* | |
H6 | 0.1229 | 0.3114 | 0.4986 | 0.070* | |
H2A | 0.3287 | 0.2076 | 0.5300 | 0.079* | |
H3A | 0.4156 | 0.0097 | 0.6531 | 0.091* | |
H5A | 0.3593 | −0.3917 | 0.4329 | 0.083* | |
H6A | 0.2720 | −0.1958 | 0.3106 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0467 (3) | 0.0727 (4) | 0.0678 (4) | 0.0047 (3) | 0.0051 (3) | 0.0227 (3) |
O1 | 0.0559 (11) | 0.0725 (13) | 0.1453 (19) | −0.0105 (9) | −0.0044 (11) | 0.0385 (12) |
O2 | 0.0734 (12) | 0.1423 (19) | 0.0526 (10) | 0.0288 (12) | 0.0180 (9) | 0.0229 (11) |
C1 | 0.0440 (12) | 0.0468 (11) | 0.0480 (11) | 0.0028 (9) | 0.0003 (9) | 0.0095 (9) |
C2 | 0.0586 (14) | 0.0534 (13) | 0.0524 (13) | 0.0033 (11) | −0.0004 (10) | −0.0062 (10) |
C3 | 0.0541 (14) | 0.0563 (14) | 0.0763 (16) | −0.0094 (11) | −0.0083 (12) | −0.0021 (12) |
C4 | 0.0511 (14) | 0.0621 (14) | 0.0732 (16) | 0.0009 (12) | 0.0133 (12) | 0.0145 (13) |
C5 | 0.0709 (17) | 0.0710 (16) | 0.0507 (14) | 0.0097 (13) | 0.0121 (12) | −0.0020 (11) |
C6 | 0.0587 (14) | 0.0634 (14) | 0.0507 (13) | −0.0001 (12) | −0.0067 (11) | −0.0044 (11) |
C1A | 0.0401 (11) | 0.0610 (14) | 0.0550 (13) | 0.0028 (10) | 0.0052 (10) | 0.0088 (11) |
C2A | 0.0554 (14) | 0.0689 (16) | 0.0723 (16) | 0.0025 (12) | −0.0069 (12) | −0.0048 (13) |
C3A | 0.0550 (15) | 0.113 (2) | 0.0588 (15) | 0.0045 (15) | −0.0095 (12) | −0.0023 (15) |
C4A | 0.0428 (13) | 0.093 (2) | 0.0693 (16) | 0.0176 (13) | 0.0111 (11) | 0.0258 (15) |
Cl4A | 0.0774 (5) | 0.1677 (9) | 0.1037 (6) | 0.0516 (6) | 0.0129 (4) | 0.0652 (6) |
C5A | 0.0613 (15) | 0.0667 (16) | 0.0803 (18) | 0.0162 (13) | 0.0118 (13) | 0.0058 (14) |
C6A | 0.0552 (14) | 0.0716 (16) | 0.0571 (14) | 0.0080 (12) | 0.0035 (11) | −0.0035 (12) |
Geometric parameters (Å, º) top
S1—O1 | 1.429 (2) | C5—H5 | 0.9300 |
S1—O2 | 1.439 (2) | C6—H6 | 0.9300 |
S1—C1 | 1.766 (2) | C1A—C2A | 1.376 (3) |
S1—C1A | 1.770 (2) | C1A—C6A | 1.377 (3) |
C1—C2 | 1.377 (3) | C2A—C3A | 1.383 (4) |
C1—C6 | 1.388 (3) | C2A—H2A | 0.9300 |
C2—C3 | 1.381 (3) | C3A—C4A | 1.371 (4) |
C2—H2 | 0.9300 | C3A—H3A | 0.9300 |
C3—C4 | 1.373 (4) | C4A—C5A | 1.370 (4) |
C3—H3 | 0.9300 | C4A—Cl4A | 1.733 (2) |
C4—C5 | 1.374 (3) | C5A—C6A | 1.374 (3) |
C4—H4 | 0.9300 | C5A—H5A | 0.9300 |
C5—C6 | 1.367 (3) | C6A—H6A | 0.9300 |
| | | |
O1—S1—O2 | 119.58 (14) | C5—C6—C1 | 119.2 (2) |
O1—S1—C1 | 107.43 (11) | C5—C6—H6 | 120.4 |
O2—S1—C1 | 107.76 (11) | C1—C6—H6 | 120.4 |
O1—S1—C1A | 107.66 (12) | C2A—C1A—C6A | 120.9 (2) |
O2—S1—C1A | 108.25 (12) | C2A—C1A—S1 | 119.79 (19) |
C1—S1—C1A | 105.30 (10) | C6A—C1A—S1 | 119.31 (18) |
C2—C1—C6 | 120.5 (2) | C1A—C2A—C3A | 118.9 (3) |
C2—C1—S1 | 119.13 (17) | C1A—C2A—H2A | 120.6 |
C6—C1—S1 | 120.32 (17) | C3A—C2A—H2A | 120.6 |
C1—C2—C3 | 119.4 (2) | C4A—C3A—C2A | 119.6 (2) |
C1—C2—H2 | 120.3 | C4A—C3A—H3A | 120.2 |
C3—C2—H2 | 120.3 | C2A—C3A—H3A | 120.2 |
C4—C3—C2 | 120.2 (2) | C5A—C4A—C3A | 121.6 (2) |
C4—C3—H3 | 119.9 | C5A—C4A—Cl4A | 119.1 (2) |
C2—C3—H3 | 119.9 | C3A—C4A—Cl4A | 119.3 (2) |
C3—C4—C5 | 119.9 (2) | C4A—C5A—C6A | 118.8 (3) |
C3—C4—H4 | 120.0 | C4A—C5A—H5A | 120.6 |
C5—C4—H4 | 120.0 | C6A—C5A—H5A | 120.6 |
C6—C5—C4 | 120.8 (2) | C5A—C6A—C1A | 120.1 (2) |
C6—C5—H5 | 119.6 | C5A—C6A—H6A | 119.9 |
C4—C5—H5 | 119.6 | C1A—C6A—H6A | 119.9 |
| | | |
O1—S1—C1—C2 | 137.28 (18) | O2—S1—C1A—C2A | 156.2 (2) |
O2—S1—C1—C2 | 7.2 (2) | C1—S1—C1A—C2A | −88.8 (2) |
C1A—S1—C1—C2 | −108.17 (18) | O1—S1—C1A—C6A | −155.3 (2) |
O1—S1—C1—C6 | −40.3 (2) | O2—S1—C1A—C6A | −24.7 (2) |
O2—S1—C1—C6 | −170.36 (18) | C1—S1—C1A—C6A | 90.3 (2) |
C1A—S1—C1—C6 | 74.3 (2) | C6A—C1A—C2A—C3A | 1.2 (4) |
C6—C1—C2—C3 | 1.7 (3) | S1—C1A—C2A—C3A | −179.7 (2) |
S1—C1—C2—C3 | −175.89 (18) | C1A—C2A—C3A—C4A | 0.2 (4) |
C1—C2—C3—C4 | −1.3 (4) | C2A—C3A—C4A—C5A | −1.3 (4) |
C2—C3—C4—C5 | −0.1 (4) | C2A—C3A—C4A—Cl4A | 178.5 (2) |
C3—C4—C5—C6 | 1.1 (4) | C3A—C4A—C5A—C6A | 1.1 (4) |
C4—C5—C6—C1 | −0.7 (4) | Cl4A—C4A—C5A—C6A | −178.73 (19) |
C2—C1—C6—C5 | −0.7 (3) | C4A—C5A—C6A—C1A | 0.2 (4) |
S1—C1—C6—C5 | 176.85 (18) | C2A—C1A—C6A—C5A | −1.4 (4) |
O1—S1—C1A—C2A | 25.6 (2) | S1—C1A—C6A—C5A | 179.52 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.58 | 3.500 (3) | 169 |
C5A—H5A···O1ii | 0.93 | 2.53 | 3.326 (4) | 143 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, y−1, z. |
(4) 3,4-Dimethyl-4'-chlorodiphenyl sulfone
top
Crystal data top
C14H13ClO2S | F(000) = 584 |
Mr = 280.75 | Dx = 1.411 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.9682 (14) Å | Cell parameters from 9255 reflections |
b = 7.5293 (12) Å | θ = 1.8–25.9° |
c = 14.4627 (17) Å | µ = 0.44 mm−1 |
β = 110.625 (7)° | T = 150 K |
V = 1321.6 (3) Å3 | Block, colourless |
Z = 4 | 0.10 × 0.08 × 0.05 mm |
Data collection top
Kappa-CCD diffractometer | 2545 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1332 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
ϕ scans and ω scans with κ offsets | θmax = 25.9°, θmin = 1.8° |
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997) | h = −15→15 |
Tmin = 0.958, Tmax = 0.979 | k = −9→9 |
9255 measured reflections | l = −17→17 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-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 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C14H13ClO2S | V = 1321.6 (3) Å3 |
Mr = 280.75 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.9682 (14) Å | µ = 0.44 mm−1 |
b = 7.5293 (12) Å | T = 150 K |
c = 14.4627 (17) Å | 0.10 × 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 = 0.979 | Rint = 0.053 |
9255 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.34 e Å−3 |
2545 reflections | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.64115 (7) | 0.17336 (16) | 0.84103 (7) | 0.0488 (4) | |
O1 | 0.6176 (2) | 0.3456 (4) | 0.87187 (19) | 0.0609 (8) | |
O2 | 0.74906 (17) | 0.0979 (4) | 0.88738 (17) | 0.0625 (9) | |
C1 | 0.6138 (3) | 0.1842 (5) | 0.7133 (2) | 0.0378 (9) | |
C2 | 0.5246 (3) | 0.2793 (6) | 0.6537 (3) | 0.0468 (11) | |
H2 | 0.4785 | 0.3401 | 0.6819 | 0.056* | |
C3 | 0.5015 (3) | 0.2870 (6) | 0.5527 (3) | 0.0497 (11) | |
H3 | 0.4394 | 0.3510 | 0.5109 | 0.060* | |
C4 | 0.5703 (3) | 0.2002 (6) | 0.5142 (2) | 0.0436 (10) | |
Cl4 | 0.54225 (8) | 0.21027 (17) | 0.38745 (7) | 0.0634 (4) | |
C5 | 0.6595 (3) | 0.1037 (6) | 0.5717 (3) | 0.0475 (10) | |
H5 | 0.7054 | 0.0441 | 0.5430 | 0.057* | |
C6 | 0.6816 (3) | 0.0947 (6) | 0.6732 (3) | 0.0468 (10) | |
H6 | 0.7426 | 0.0279 | 0.7145 | 0.056* | |
C1A | 0.5443 (3) | 0.0221 (6) | 0.8552 (2) | 0.0442 (10) | |
C2A | 0.4469 (3) | 0.0854 (6) | 0.8613 (2) | 0.0488 (11) | |
H2A | 0.4336 | 0.2097 | 0.8588 | 0.059* | |
C3A | 0.3672 (3) | −0.0319 (7) | 0.8711 (2) | 0.0508 (11) | |
C31A | 0.2618 (3) | 0.0406 (8) | 0.8757 (3) | 0.0786 (17) | |
H13A | 0.1996 | −0.0082 | 0.8211 | 0.118* | |
H23A | 0.2619 | 0.1704 | 0.8702 | 0.118* | |
H33A | 0.2548 | 0.0073 | 0.9387 | 0.118* | |
C4A | 0.3885 (3) | −0.2130 (7) | 0.8747 (2) | 0.0555 (12) | |
C41A | 0.3031 (4) | −0.3431 (7) | 0.8836 (3) | 0.0745 (15) | |
H14A | 0.2860 | −0.3156 | 0.9429 | 0.112* | |
H24A | 0.3321 | −0.4642 | 0.8884 | 0.112* | |
H34A | 0.2359 | −0.3334 | 0.8251 | 0.112* | |
C5A | 0.4869 (4) | −0.2747 (7) | 0.8702 (3) | 0.0644 (13) | |
H5A | 0.5011 | −0.3987 | 0.8740 | 0.077* | |
C6A | 0.5656 (3) | −0.1583 (7) | 0.8602 (2) | 0.0539 (12) | |
H6A | 0.6329 | −0.2020 | 0.8567 | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0390 (5) | 0.0710 (9) | 0.0320 (5) | −0.0065 (5) | 0.0068 (4) | −0.0049 (5) |
O1 | 0.0668 (17) | 0.066 (2) | 0.0502 (16) | −0.0067 (16) | 0.0216 (14) | −0.0174 (15) |
O2 | 0.0336 (14) | 0.104 (3) | 0.0393 (15) | −0.0012 (15) | −0.0005 (11) | 0.0047 (15) |
C1 | 0.0293 (17) | 0.048 (3) | 0.0330 (18) | −0.0064 (17) | 0.0065 (15) | −0.0031 (18) |
C2 | 0.035 (2) | 0.060 (3) | 0.044 (2) | −0.0017 (19) | 0.0130 (18) | −0.002 (2) |
C3 | 0.0357 (19) | 0.062 (3) | 0.043 (2) | −0.0065 (19) | 0.0038 (18) | 0.008 (2) |
C4 | 0.043 (2) | 0.053 (3) | 0.0322 (19) | −0.0164 (19) | 0.0097 (17) | −0.0033 (18) |
Cl4 | 0.0670 (7) | 0.0837 (10) | 0.0361 (6) | −0.0220 (6) | 0.0138 (5) | −0.0003 (5) |
C5 | 0.042 (2) | 0.056 (3) | 0.047 (2) | −0.0066 (19) | 0.0184 (18) | −0.006 (2) |
C6 | 0.0374 (19) | 0.061 (3) | 0.039 (2) | −0.0031 (19) | 0.0096 (17) | −0.005 (2) |
C1A | 0.037 (2) | 0.062 (3) | 0.0275 (19) | 0.006 (2) | 0.0045 (15) | −0.0042 (19) |
C2A | 0.045 (2) | 0.069 (3) | 0.0278 (19) | 0.011 (2) | 0.0073 (16) | 0.0081 (19) |
C3A | 0.038 (2) | 0.082 (4) | 0.0282 (19) | 0.002 (2) | 0.0069 (15) | 0.004 (2) |
C31A | 0.059 (3) | 0.126 (5) | 0.054 (3) | 0.010 (3) | 0.026 (2) | 0.015 (3) |
C4A | 0.050 (2) | 0.090 (4) | 0.025 (2) | −0.010 (3) | 0.0104 (17) | −0.002 (2) |
C41A | 0.088 (3) | 0.095 (5) | 0.043 (2) | −0.030 (3) | 0.027 (2) | −0.008 (2) |
C5A | 0.081 (3) | 0.066 (4) | 0.038 (2) | −0.002 (3) | 0.009 (2) | −0.002 (2) |
C6A | 0.048 (2) | 0.074 (4) | 0.035 (2) | −0.001 (2) | 0.0094 (18) | −0.002 (2) |
Geometric parameters (Å, º) top
S1—O2 | 1.439 (3) | C1A—C6A | 1.383 (6) |
S1—O1 | 1.439 (3) | C2A—C3A | 1.403 (6) |
S1—C1 | 1.756 (3) | C2A—H2A | 0.9500 |
S1—C1A | 1.760 (4) | C3A—C4A | 1.388 (6) |
C1—C2 | 1.376 (5) | C3A—C31A | 1.496 (5) |
C1—C6 | 1.387 (5) | C31A—H13A | 0.9800 |
C2—C3 | 1.385 (5) | C31A—H23A | 0.9800 |
C2—H2 | 0.9500 | C31A—H33A | 0.9800 |
C3—C4 | 1.372 (5) | C4A—C5A | 1.382 (6) |
C3—H3 | 0.9500 | C4A—C41A | 1.517 (6) |
C4—C5 | 1.371 (5) | C41A—H14A | 0.9800 |
C4—Cl4 | 1.741 (3) | C41A—H24A | 0.9800 |
C5—C6 | 1.394 (5) | C41A—H34A | 0.9800 |
C5—H5 | 0.9500 | C5A—C6A | 1.391 (6) |
C6—H6 | 0.9500 | C5A—H5A | 0.9500 |
C1A—C2A | 1.382 (5) | C6A—H6A | 0.9500 |
| | | |
O2—S1—O1 | 119.32 (17) | C1A—C2A—C3A | 120.7 (4) |
O2—S1—C1 | 108.17 (16) | C1A—C2A—H2A | 119.6 |
O1—S1—C1 | 107.33 (17) | C3A—C2A—H2A | 119.6 |
O2—S1—C1A | 107.87 (18) | C4A—C3A—C2A | 118.6 (4) |
O1—S1—C1A | 107.98 (18) | C4A—C3A—C31A | 122.0 (4) |
C1—S1—C1A | 105.34 (15) | C2A—C3A—C31A | 119.4 (5) |
C2—C1—C6 | 120.5 (3) | C3A—C31A—H13A | 109.5 |
C2—C1—S1 | 119.9 (3) | C3A—C31A—H23A | 109.5 |
C6—C1—S1 | 119.6 (3) | H13A—C31A—H23A | 109.5 |
C1—C2—C3 | 120.3 (4) | C3A—C31A—H33A | 109.5 |
C1—C2—H2 | 119.9 | H13A—C31A—H33A | 109.5 |
C3—C2—H2 | 119.9 | H23A—C31A—H33A | 109.5 |
C4—C3—C2 | 118.6 (3) | C5A—C4A—C3A | 120.2 (4) |
C4—C3—H3 | 120.7 | C5A—C4A—C41A | 120.1 (5) |
C2—C3—H3 | 120.7 | C3A—C4A—C41A | 119.7 (4) |
C3—C4—C5 | 122.5 (3) | C4A—C41A—H14A | 109.5 |
C3—C4—Cl4 | 118.8 (3) | C4A—C41A—H24A | 109.5 |
C5—C4—Cl4 | 118.7 (3) | H14A—C41A—H24A | 109.5 |
C4—C5—C6 | 118.7 (4) | C4A—C41A—H34A | 109.5 |
C4—C5—H5 | 120.6 | H14A—C41A—H34A | 109.5 |
C6—C5—H5 | 120.6 | H24A—C41A—H34A | 109.5 |
C1—C6—C5 | 119.4 (3) | C4A—C5A—C6A | 121.1 (5) |
C1—C6—H6 | 120.3 | C4A—C5A—H5A | 119.4 |
C5—C6—H6 | 120.3 | C6A—C5A—H5A | 119.4 |
C2A—C1A—C6A | 120.4 (4) | C1A—C6A—C5A | 118.9 (4) |
C2A—C1A—S1 | 119.4 (4) | C1A—C6A—H6A | 120.5 |
C6A—C1A—S1 | 120.2 (3) | C5A—C6A—H6A | 120.5 |
| | | |
O2—S1—C1—C2 | −168.6 (3) | C1—S1—C1A—C2A | −94.8 (3) |
O1—S1—C1—C2 | −38.6 (3) | O2—S1—C1A—C6A | −30.2 (3) |
C1A—S1—C1—C2 | 76.3 (3) | O1—S1—C1A—C6A | −160.4 (3) |
O2—S1—C1—C6 | 12.2 (4) | C1—S1—C1A—C6A | 85.1 (3) |
O1—S1—C1—C6 | 142.2 (3) | C6A—C1A—C2A—C3A | −0.9 (5) |
C1A—S1—C1—C6 | −102.9 (3) | S1—C1A—C2A—C3A | 179.0 (2) |
C6—C1—C2—C3 | −0.1 (6) | C1A—C2A—C3A—C4A | 0.1 (5) |
S1—C1—C2—C3 | −179.3 (3) | C1A—C2A—C3A—C31A | −179.0 (3) |
C1—C2—C3—C4 | −1.0 (6) | C2A—C3A—C4A—C5A | 0.9 (5) |
C2—C3—C4—C5 | 1.3 (6) | C31A—C3A—C4A—C5A | 180.0 (3) |
C2—C3—C4—Cl4 | −179.7 (3) | C2A—C3A—C4A—C41A | −179.0 (3) |
C3—C4—C5—C6 | −0.5 (6) | C31A—C3A—C4A—C41A | 0.1 (5) |
Cl4—C4—C5—C6 | −179.6 (3) | C3A—C4A—C5A—C6A | −1.2 (6) |
C2—C1—C6—C5 | 0.8 (6) | C41A—C4A—C5A—C6A | 178.7 (3) |
S1—C1—C6—C5 | 180.0 (3) | C2A—C1A—C6A—C5A | 0.7 (5) |
C4—C5—C6—C1 | −0.5 (6) | S1—C1A—C6A—C5A | −179.2 (3) |
O2—S1—C1A—C2A | 149.9 (3) | C4A—C5A—C6A—C1A | 0.4 (6) |
O1—S1—C1A—C2A | 19.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.52 | 3.416 (5) | 158 |
C5A—H5A···O1ii | 0.95 | 2.45 | 3.319 (6) | 151 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y−1, z. |
(5) 2,5-Dimethyldiphenyl sulfone
top
Crystal data top
C14H14O2S | F(000) = 520 |
Mr = 246.31 | Dx = 1.274 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8879 (3) Å | Cell parameters from 14179 reflections |
b = 10.9788 (4) Å | θ = 2.3–27.3° |
c = 15.2489 (4) Å | µ = 0.24 mm−1 |
β = 103.525 (2)° | T = 150 K |
V = 1283.93 (8) Å3 | Plate, colourless |
Z = 4 | 0.20 × 0.15 × 0.05 mm |
Data collection top
Kappa-CCD diffractometer | 2895 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1990 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ϕ scans and ω scans with κ offsets | θmax = 27.3°, θmin = 2.3° |
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997) | h = −10→10 |
Tmin = 0.954, Tmax = 0.988 | k = −14→14 |
14179 measured reflections | l = −19→19 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-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 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
Crystal data top
C14H14O2S | V = 1283.93 (8) Å3 |
Mr = 246.31 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.8879 (3) Å | µ = 0.24 mm−1 |
b = 10.9788 (4) Å | T = 150 K |
c = 15.2489 (4) Å | 0.20 × 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 = 0.988 | Rint = 0.038 |
14179 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.26 e Å−3 |
2895 reflections | Δρmin = −0.42 e Å−3 |
156 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.19274 (6) | 0.75337 (4) | 0.29672 (3) | 0.02638 (17) | |
O1 | 0.10507 (17) | 0.83517 (12) | 0.22674 (8) | 0.0321 (3) | |
O2 | 0.34797 (16) | 0.69367 (13) | 0.28465 (8) | 0.0349 (4) | |
C1 | 0.0404 (2) | 0.64101 (17) | 0.30893 (11) | 0.0255 (4) | |
C2 | −0.1252 (2) | 0.67689 (19) | 0.31517 (12) | 0.0324 (5) | |
C3 | −0.2478 (3) | 0.5878 (2) | 0.32019 (13) | 0.0403 (5) | |
C4 | −0.2047 (3) | 0.4665 (2) | 0.31915 (13) | 0.0407 (5) | |
C5 | −0.0401 (3) | 0.4319 (2) | 0.31243 (13) | 0.0393 (5) | |
C6 | 0.0845 (3) | 0.51890 (18) | 0.30783 (12) | 0.0329 (5) | |
C1A | 0.2399 (2) | 0.83687 (17) | 0.39923 (11) | 0.0270 (4) | |
C2A | 0.3324 (3) | 0.7831 (2) | 0.48037 (12) | 0.0330 (5) | |
C2A1 | 0.3947 (3) | 0.6532 (2) | 0.48952 (13) | 0.0424 (6) | |
C3A | 0.3638 (3) | 0.8588 (2) | 0.55521 (13) | 0.0406 (5) | |
C4A | 0.3093 (3) | 0.9785 (2) | 0.55117 (13) | 0.0422 (6) | |
C5A | 0.2183 (3) | 1.0306 (2) | 0.47111 (12) | 0.0356 (5) | |
C5A1 | 0.1602 (3) | 1.1611 (2) | 0.46530 (15) | 0.0502 (6) | |
C6A | 0.1843 (2) | 0.95648 (19) | 0.39489 (12) | 0.0312 (5) | |
H2 | −0.1542 | 0.7608 | 0.3160 | 0.039* | |
H3 | −0.3618 | 0.6108 | 0.3244 | 0.048* | |
H4 | −0.2888 | 0.4061 | 0.3231 | 0.049* | |
H5 | −0.0121 | 0.3479 | 0.3109 | 0.047* | |
H6 | 0.1984 | 0.4953 | 0.3040 | 0.040* | |
H2A1 | 0.4631 | 0.6391 | 0.5511 | 0.064* | |
H2A2 | 0.4676 | 0.6376 | 0.4467 | 0.064* | |
H2A3 | 0.2940 | 0.5982 | 0.4767 | 0.064* | |
H3A | 0.4253 | 0.8269 | 0.6116 | 0.049* | |
H4A | 0.3346 | 1.0264 | 0.6045 | 0.051* | |
H5A1 | 0.2250 | 1.2055 | 0.5184 | 0.075* | |
H5A2 | 0.0352 | 1.1648 | 0.4632 | 0.075* | |
H5A3 | 0.1825 | 1.1981 | 0.4106 | 0.075* | |
H6A | 0.1217 | 0.9888 | 0.3389 | 0.037* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0249 (3) | 0.0316 (3) | 0.0225 (3) | −0.0009 (2) | 0.00526 (18) | −0.00011 (19) |
O1 | 0.0359 (8) | 0.0346 (9) | 0.0229 (6) | −0.0027 (6) | 0.0011 (5) | 0.0035 (5) |
O2 | 0.0259 (7) | 0.0454 (9) | 0.0360 (7) | 0.0015 (7) | 0.0124 (5) | −0.0017 (6) |
C1 | 0.0232 (9) | 0.0327 (12) | 0.0197 (9) | 0.0015 (8) | 0.0035 (7) | −0.0007 (7) |
C2 | 0.0289 (11) | 0.0356 (13) | 0.0332 (10) | 0.0046 (9) | 0.0079 (8) | −0.0003 (9) |
C3 | 0.0256 (11) | 0.0554 (16) | 0.0419 (12) | −0.0031 (10) | 0.0121 (8) | −0.0028 (10) |
C4 | 0.0415 (13) | 0.0435 (15) | 0.0383 (11) | −0.0144 (11) | 0.0118 (9) | −0.0039 (9) |
C5 | 0.0475 (14) | 0.0274 (12) | 0.0436 (12) | −0.0043 (10) | 0.0115 (9) | −0.0007 (9) |
C6 | 0.0315 (11) | 0.0313 (13) | 0.0358 (11) | 0.0045 (9) | 0.0077 (8) | −0.0012 (8) |
C1A | 0.0253 (10) | 0.0304 (12) | 0.0245 (9) | −0.0036 (8) | 0.0040 (7) | 0.0000 (8) |
C2A | 0.0295 (11) | 0.0423 (13) | 0.0257 (10) | −0.0012 (9) | 0.0034 (7) | 0.0049 (8) |
C2A1 | 0.0490 (13) | 0.0451 (15) | 0.0287 (11) | 0.0069 (11) | −0.0001 (9) | 0.0079 (9) |
C3A | 0.0405 (12) | 0.0528 (15) | 0.0245 (10) | −0.0018 (11) | −0.0005 (8) | 0.0006 (9) |
C4A | 0.0474 (14) | 0.0509 (15) | 0.0274 (10) | −0.0073 (11) | 0.0069 (9) | −0.0105 (9) |
C5A | 0.0386 (12) | 0.0350 (13) | 0.0345 (11) | −0.0049 (9) | 0.0115 (8) | −0.0037 (9) |
C5A1 | 0.0645 (16) | 0.0398 (14) | 0.0476 (13) | 0.0036 (12) | 0.0160 (11) | −0.0071 (10) |
C6A | 0.0309 (11) | 0.0352 (12) | 0.0271 (10) | −0.0019 (9) | 0.0061 (7) | 0.0011 (8) |
Geometric parameters (Å, º) top
S1—O2 | 1.4381 (14) | C1A—C2A | 1.411 (2) |
S1—O1 | 1.4416 (13) | C2A—C3A | 1.386 (3) |
S1—C1 | 1.7624 (19) | C2A—C2A1 | 1.505 (3) |
S1—C1A | 1.7748 (18) | C2A1—H2A1 | 0.9800 |
C1—C6 | 1.386 (3) | C2A1—H2A2 | 0.9800 |
C1—C2 | 1.388 (3) | C2A1—H2A3 | 0.9800 |
C2—C3 | 1.390 (3) | C3A—C4A | 1.380 (3) |
C2—H2 | 0.9500 | C3A—H3A | 0.9500 |
C3—C4 | 1.376 (3) | C4A—C5A | 1.386 (3) |
C3—H3 | 0.9500 | C4A—H4A | 0.9500 |
C4—C5 | 1.379 (3) | C5A—C6A | 1.392 (3) |
C4—H4 | 0.9500 | C5A—C5A1 | 1.500 (3) |
C5—C6 | 1.384 (3) | C5A1—H5A1 | 0.9800 |
C5—H5 | 0.9500 | C5A1—H5A2 | 0.9800 |
C6—H6 | 0.9500 | C5A1—H5A3 | 0.9800 |
C1A—C6A | 1.381 (3) | C6A—H6A | 0.9500 |
| | | |
O2—S1—O1 | 117.69 (8) | C3A—C2A—C1A | 115.31 (19) |
O2—S1—C1 | 108.46 (9) | C3A—C2A—C2A1 | 120.01 (17) |
O1—S1—C1 | 107.06 (8) | C1A—C2A—C2A1 | 124.67 (17) |
O2—S1—C1A | 109.81 (8) | C2A—C2A1—H2A1 | 109.5 |
O1—S1—C1A | 107.19 (8) | C2A—C2A1—H2A2 | 109.5 |
C1—S1—C1A | 106.02 (8) | H2A1—C2A1—H2A2 | 109.5 |
C6—C1—C2 | 121.20 (18) | C2A—C2A1—H2A3 | 109.5 |
C6—C1—S1 | 119.75 (14) | H2A1—C2A1—H2A3 | 109.5 |
C2—C1—S1 | 118.97 (15) | H2A2—C2A1—H2A3 | 109.5 |
C1—C2—C3 | 118.8 (2) | C4A—C3A—C2A | 122.70 (18) |
C1—C2—H2 | 120.6 | C4A—C3A—H3A | 118.6 |
C3—C2—H2 | 120.6 | C2A—C3A—H3A | 118.6 |
C4—C3—C2 | 120.2 (2) | C3A—C4A—C5A | 121.57 (19) |
C4—C3—H3 | 119.9 | C3A—C4A—H4A | 119.2 |
C2—C3—H3 | 119.9 | C5A—C4A—H4A | 119.2 |
C3—C4—C5 | 120.4 (2) | C4A—C5A—C6A | 117.0 (2) |
C3—C4—H4 | 119.8 | C4A—C5A—C5A1 | 122.24 (19) |
C5—C4—H4 | 119.8 | C6A—C5A—C5A1 | 120.80 (18) |
C4—C5—C6 | 120.4 (2) | C5A—C5A1—H5A1 | 109.5 |
C4—C5—H5 | 119.8 | C5A—C5A1—H5A2 | 109.5 |
C6—C5—H5 | 119.8 | H5A1—C5A1—H5A2 | 109.5 |
C5—C6—C1 | 118.91 (19) | C5A—C5A1—H5A3 | 109.5 |
C5—C6—H6 | 120.5 | H5A1—C5A1—H5A3 | 109.5 |
C1—C6—H6 | 120.5 | H5A2—C5A1—H5A3 | 109.5 |
C6A—C1A—C2A | 122.22 (17) | C1A—C6A—C5A | 121.23 (17) |
C6A—C1A—S1 | 116.76 (13) | C1A—C6A—H6A | 119.4 |
C2A—C1A—S1 | 121.01 (15) | C5A—C6A—H6A | 119.4 |
| | | |
O2—S1—C1—C6 | 1.42 (16) | O2—S1—C1A—C2A | −48.49 (17) |
O1—S1—C1—C6 | 129.35 (14) | O1—S1—C1A—C2A | −177.42 (14) |
C1A—S1—C1—C6 | −116.46 (14) | C1—S1—C1A—C2A | 68.48 (17) |
O2—S1—C1—C2 | −175.52 (13) | C6A—C1A—C2A—C3A | −0.1 (3) |
O1—S1—C1—C2 | −47.58 (15) | S1—C1A—C2A—C3A | 178.74 (15) |
C1A—S1—C1—C2 | 66.61 (15) | C6A—C1A—C2A—C2A1 | 179.4 (2) |
C6—C1—C2—C3 | −0.1 (3) | S1—C1A—C2A—C2A1 | −1.8 (3) |
S1—C1—C2—C3 | 176.78 (14) | C1A—C2A—C3A—C4A | −0.2 (3) |
C1—C2—C3—C4 | 0.1 (3) | C2A1—C2A—C3A—C4A | −179.7 (2) |
C2—C3—C4—C5 | −0.5 (3) | C2A—C3A—C4A—C5A | 0.2 (3) |
C3—C4—C5—C6 | 0.9 (3) | C3A—C4A—C5A—C6A | 0.0 (3) |
C4—C5—C6—C1 | −0.8 (3) | C3A—C4A—C5A—C5A1 | −179.2 (2) |
C2—C1—C6—C5 | 0.5 (3) | C2A—C1A—C6A—C5A | 0.4 (3) |
S1—C1—C6—C5 | −176.41 (13) | S1—C1A—C6A—C5A | −178.51 (15) |
O2—S1—C1A—C6A | 130.43 (15) | C4A—C5A—C6A—C1A | −0.4 (3) |
O1—S1—C1A—C6A | 1.50 (17) | C5A1—C5A—C6A—C1A | 178.88 (19) |
C1—S1—C1A—C6A | −112.60 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.41 | 3.317 (3) | 161 |
C4—H4···O1ii | 0.95 | 2.55 | 3.392 (3) | 147 |
C6—H6···O1iii | 0.95 | 2.46 | 3.309 (3) | 149 |
Symmetry codes: (i) x−1, y, z; (ii) −x−1/2, y−1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2. |
Experimental details
| (1) | (2) | (3) | (4) |
Crystal data |
Chemical formula | C14H14O2S | C15H16O2S | C12H9ClO2S | C14H13ClO2S |
Mr | 246.31 | 260.34 | 252.70 | 280.75 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/n | Monoclinic, P21/c | Monoclinic, P21/n |
Temperature (K) | 306 | 150 | 307 | 150 |
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) |
V (Å3) | 2586.3 (2) | 1347.95 (14) | 1156.3 (4) | 1321.6 (3) |
Z | 8 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.24 | 0.23 | 0.49 | 0.44 |
Crystal size (mm) | 0.56 × 0.18 × 0.13 | 0.2 × 0.2 × 0.03 | 0.40 × 0.28 × 0.24 | 0.10 × 0.08 × 0.05 |
|
Data collection |
Diffractometer | Bruker SMART 1000 CCD diffractometer | Kappa-CCD diffractometer | Bruker SMART 1000 CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan SADABS (Bruker, 1997) | Multi-scan SORTAV (Blessing, 1995 & 1997) | Multi-scan SADABS (Bruker, 1997) | Multi-scan SORTAV (Blessing, 1995 & 1997) |
Tmin, Tmax | 0.879, 0.970 | 0.929, 0.969 | 0.828, 0.891 | 0.958, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15872, 4554, 2746 | 12210, 3060, 2172 | 7000, 2030, 1527 | 9255, 2545, 1332 |
Rint | 0.023 | 0.037 | 0.020 | 0.053 |
(sin θ/λ)max (Å−1) | 0.595 | 0.647 | 0.595 | 0.613 |
|
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 reflections | 4554 | 3060 | 2030 | 2545 |
No. of parameters | 311 | 166 | 145 | 165 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.23 | 0.24, −0.44 | 0.24, −0.40 | 0.34, −0.28 |
| (5) |
Crystal data |
Chemical formula | C14H14O2S |
Mr | 246.31 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 7.8879 (3), 10.9788 (4), 15.2489 (4) |
β (°) | 103.525 (2) |
V (Å3) | 1283.93 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.20 × 0.15 × 0.05 |
|
Data collection |
Diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan SORTAV (Blessing, 1995 & 1997) |
Tmin, Tmax | 0.954, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14179, 2895, 1990 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.646 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.122, 1.04 |
No. of reflections | 2895 |
No. of parameters | 156 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.42 |
Hydrogen-bond geometry (Å, º) for (1) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15A—H15A···O2Ai | 0.93 | 2.44 | 3.354 (3) | 166 |
C5B—H5B···O2Bi | 0.93 | 2.58 | 3.317 (3) | 137 |
Symmetry code: (i) x, y+1, z. |
Hydrogen-bond geometry (Å, º) for (2) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4A—H4A···O2i | 0.93 | 2.43 | 3.292 (2) | 154 |
C2—H2···O2ii | 0.93 | 2.59 | 3.306 (2) | 134 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) for (3) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.58 | 3.500 (3) | 169 |
C5A—H5A···O1ii | 0.93 | 2.53 | 3.326 (4) | 143 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, y−1, z. |
Hydrogen-bond geometry (Å, º) for (4) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.52 | 3.416 (5) | 158 |
C5A—H5A···O1ii | 0.95 | 2.45 | 3.319 (6) | 151 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, y−1, z. |
Hydrogen-bond geometry (Å, º) for (5) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.41 | 3.317 (3) | 161 |
C4—H4···O1ii | 0.95 | 2.55 | 3.392 (3) | 147 |
C6—H6···O1iii | 0.95 | 2.46 | 3.309 (3) | 149 |
Symmetry codes: (i) x−1, y, z; (ii) −x−1/2, y−1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2. |
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