organic compounds
Bis[4-(2-hydroxyethylamino)phenyl] sulfone
aDepartment of Chemistry, Tianjin University, Tianjin 300072, People's Republic of China, and bDepartment of Chemistry, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, People's Republic of China
*Correspondence e-mail: chenguofeng@mail.hbu.edu.cn
The title compound, C16H20N2O4S, exhibits a V-shape structure with a dihedral angle of 77.5 (11)° formed by the two benzenel rings. The molecular packing is stabilized by intramolecular and intermolecular hydrogen bonds as well as π–π [3.738 (3) Å] and C—H⋯π interactions.
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536807063805/bx2122sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063805/bx2122Isup2.hkl
The title compound, (I), was synthesized by the reaction of 4,4'-dichlorodiphenyl sulfone (5.74 g, 0.02 mol) with 2-aminoethanol (9.76 g, 0.16 mol). The mixture was refluxed for 6 h and cooled to room temperature. After dilution with water, it was filtered off, washed thoroughly with water, and recrystallized from dimethylformamide and water (4:1 v/v) to give the product as fine white needles (5.5 g, yield 81.8%). The pure product (0.1 g) was dissolved in 15 ml dimethylformamide and water (4:1 v/v). Single crystals were obtained from this solution by slow evaporation over a period of 7 days at room temperature (m.p. 464–466 K).
The H atom involved in the hydrogen bonds was found in difference Fourier maps. All other H atoms were positioned geometrically and refined using a during
fix at O–H distances of 0.82 Å and its Uiso value was set at 1.2 Ueq (O). H atoms bonded to C atoms were included in the in the riding model approximation, with C–H = 0.93 Å. and Uiso (H) = 1.2 Ueq (C atom).The derivatives of diphenyl sulphone are used as precursors in the organic synthesis. Several derivatives of aminosulphones have been shown to possess strong tuberculostatic, antileprotic and anticonvulsant activities (Shahsafi, et al., 1987). The
determination of the title compound, (I), was carried out in order to elucidate its molecular conformation.The V-shape structure of the molecule is supported by the two phenyl rings with a dihedral angle of 77.5 (11)°.
The molecular packing is stabilized by intramolecular and intermolecular hydrogen bonds (Table 1) as well as weak π-π and C—H..π interactions.
For related literature, see: Shahsafi et al. (1987).
Data collection: SMART (Bruker, 1997); cell
SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).Fig. 1. A view of the structure of (I), showing the atom-numbering Scheme; displacement ellipsoids were drawn at the 30% probability level. |
C16H20N2O4S | F(000) = 1424 |
Mr = 336.40 | Dx = 1.436 Mg m−3 |
Monoclinic, C2/c | Melting point: 465(1) K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 25.643 (17) Å | Cell parameters from 2679 reflections |
b = 8.118 (6) Å | θ = 2.6–26.4° |
c = 15.340 (11) Å | µ = 0.23 mm−1 |
β = 102.989 (12)° | T = 294 K |
V = 3112 (4) Å3 | Needle, colorless |
Z = 8 | 0.20 × 0.18 × 0.16 mm |
Bruker SMART CCD area-detector diffractometer | 2742 independent reflections |
Radiation source: fine-focus sealed tube | 1982 reflections with I > 2σ |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −26→30 |
Tmin = 0.953, Tmax = 0.966 | k = −9→9 |
7793 measured reflections | l = −15→18 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.055P)2 + 1.5895P] where P = (Fo2 + 2Fc2)/3 |
2742 reflections | (Δ/σ)max = 0.005 |
218 parameters | Δρmax = 0.22 e Å−3 |
2 restraints | Δρmin = −0.35 e Å−3 |
C16H20N2O4S | V = 3112 (4) Å3 |
Mr = 336.40 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.643 (17) Å | µ = 0.23 mm−1 |
b = 8.118 (6) Å | T = 294 K |
c = 15.340 (11) Å | 0.20 × 0.18 × 0.16 mm |
β = 102.989 (12)° |
Bruker SMART CCD area-detector diffractometer | 2742 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1982 reflections with I > 2σ |
Tmin = 0.953, Tmax = 0.966 | Rint = 0.033 |
7793 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 2 restraints |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.22 e Å−3 |
2742 reflections | Δρmin = −0.35 e Å−3 |
218 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.13804 (2) | 0.13061 (7) | 0.27577 (4) | 0.0437 (2) | |
O1 | −0.11464 (7) | 0.7991 (2) | 0.07807 (12) | 0.0614 (5) | |
H1 | −0.1153 | 0.8496 | 0.1241 | 0.092* | |
O2 | 0.16477 (7) | 0.1933 (2) | 0.36085 (10) | 0.0575 (5) | |
O3 | 0.11181 (7) | −0.0265 (2) | 0.27233 (11) | 0.0551 (5) | |
O4 | 0.37876 (7) | −0.1123 (3) | 0.00979 (13) | 0.0656 (5) | |
H4 | 0.3659 | −0.1633 | 0.0460 | 0.098* | |
N1 | −0.02318 (8) | 0.5964 (3) | 0.09390 (13) | 0.0496 (5) | |
N2 | 0.29293 (8) | 0.0802 (3) | 0.05074 (14) | 0.0479 (5) | |
C1 | −0.06999 (11) | 0.8469 (3) | 0.04713 (18) | 0.0605 (7) | |
H1A | −0.0667 | 0.9659 | 0.0504 | 0.073* | |
H1B | −0.0749 | 0.8150 | −0.0151 | 0.073* | |
C2 | −0.01965 (10) | 0.7710 (3) | 0.09995 (18) | 0.0541 (7) | |
H2A | 0.0106 | 0.8089 | 0.0771 | 0.065* | |
H2B | −0.0140 | 0.8045 | 0.1621 | 0.065* | |
C3 | 0.01441 (8) | 0.4931 (3) | 0.13841 (14) | 0.0395 (5) | |
C4 | 0.06235 (9) | 0.5465 (3) | 0.19253 (16) | 0.0455 (6) | |
H4A | 0.0692 | 0.6588 | 0.1996 | 0.055* | |
C5 | 0.09948 (9) | 0.4366 (3) | 0.23534 (16) | 0.0452 (6) | |
H5 | 0.1314 | 0.4743 | 0.2712 | 0.054* | |
C6 | 0.09002 (8) | 0.2708 (3) | 0.22587 (14) | 0.0370 (5) | |
C7 | 0.04241 (9) | 0.2161 (3) | 0.17295 (15) | 0.0436 (6) | |
H7 | 0.0358 | 0.1036 | 0.1664 | 0.052* | |
C8 | 0.00543 (9) | 0.3235 (3) | 0.13085 (15) | 0.0449 (6) | |
H8 | −0.0267 | 0.2844 | 0.0961 | 0.054* | |
C9 | 0.18453 (8) | 0.1155 (3) | 0.21042 (14) | 0.0380 (5) | |
C10 | 0.23154 (9) | 0.2043 (3) | 0.23028 (15) | 0.0441 (6) | |
H10 | 0.2389 | 0.2729 | 0.2801 | 0.053* | |
C11 | 0.26711 (9) | 0.1918 (3) | 0.17704 (16) | 0.0450 (6) | |
H11 | 0.2989 | 0.2510 | 0.1914 | 0.054* | |
C12 | 0.25677 (9) | 0.0920 (3) | 0.10144 (14) | 0.0378 (5) | |
C13 | 0.20852 (8) | 0.0063 (3) | 0.08150 (15) | 0.0407 (5) | |
H13 | 0.2002 | −0.0593 | 0.0305 | 0.049* | |
C14 | 0.17353 (9) | 0.0173 (3) | 0.13568 (15) | 0.0424 (6) | |
H14 | 0.1418 | −0.0423 | 0.1221 | 0.051* | |
C15 | 0.28658 (9) | −0.0244 (3) | −0.02587 (15) | 0.0465 (6) | |
H15A | 0.2595 | 0.0214 | −0.0743 | 0.056* | |
H15B | 0.2745 | −0.1321 | −0.0115 | 0.056* | |
C16 | 0.33752 (10) | −0.0418 (4) | −0.05525 (17) | 0.0554 (7) | |
H16A | 0.3313 | −0.1096 | −0.1087 | 0.066* | |
H16B | 0.3489 | 0.0661 | −0.0709 | 0.066* | |
H1C | −0.0542 (6) | 0.548 (3) | 0.0693 (15) | 0.053 (7)* | |
H2C | 0.3197 (7) | 0.153 (2) | 0.0623 (15) | 0.049 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0429 (3) | 0.0529 (4) | 0.0352 (3) | 0.0069 (3) | 0.0084 (2) | 0.0087 (3) |
O1 | 0.0496 (10) | 0.0687 (12) | 0.0647 (12) | 0.0064 (9) | 0.0100 (9) | −0.0226 (10) |
O2 | 0.0570 (10) | 0.0800 (13) | 0.0318 (9) | 0.0134 (10) | 0.0023 (8) | 0.0028 (8) |
O3 | 0.0590 (10) | 0.0523 (10) | 0.0570 (11) | −0.0009 (9) | 0.0190 (9) | 0.0179 (8) |
O4 | 0.0422 (10) | 0.0902 (15) | 0.0653 (12) | 0.0090 (10) | 0.0144 (9) | 0.0052 (11) |
N1 | 0.0434 (12) | 0.0531 (13) | 0.0481 (12) | 0.0080 (11) | 0.0016 (10) | −0.0008 (10) |
N2 | 0.0427 (11) | 0.0510 (12) | 0.0521 (12) | −0.0059 (10) | 0.0150 (10) | −0.0089 (10) |
C1 | 0.0681 (18) | 0.0621 (17) | 0.0520 (16) | 0.0196 (15) | 0.0147 (14) | 0.0100 (14) |
C2 | 0.0517 (15) | 0.0544 (16) | 0.0578 (16) | 0.0082 (13) | 0.0157 (12) | 0.0068 (13) |
C3 | 0.0367 (12) | 0.0505 (14) | 0.0329 (12) | 0.0077 (11) | 0.0113 (10) | 0.0001 (10) |
C4 | 0.0424 (13) | 0.0445 (14) | 0.0500 (14) | 0.0024 (11) | 0.0111 (11) | 0.0014 (11) |
C5 | 0.0362 (12) | 0.0540 (15) | 0.0442 (13) | −0.0014 (11) | 0.0064 (10) | 0.0011 (11) |
C6 | 0.0331 (11) | 0.0470 (13) | 0.0325 (11) | 0.0049 (10) | 0.0103 (9) | 0.0036 (10) |
C7 | 0.0421 (13) | 0.0457 (14) | 0.0436 (13) | 0.0019 (12) | 0.0110 (11) | −0.0027 (11) |
C8 | 0.0359 (12) | 0.0553 (15) | 0.0413 (13) | 0.0018 (11) | 0.0043 (10) | −0.0075 (11) |
C9 | 0.0347 (11) | 0.0411 (12) | 0.0361 (12) | 0.0082 (10) | 0.0034 (9) | 0.0048 (10) |
C10 | 0.0430 (13) | 0.0439 (14) | 0.0426 (13) | 0.0038 (11) | 0.0040 (10) | −0.0037 (11) |
C11 | 0.0371 (12) | 0.0441 (13) | 0.0518 (15) | −0.0028 (11) | 0.0060 (11) | −0.0040 (12) |
C12 | 0.0361 (11) | 0.0375 (12) | 0.0386 (12) | 0.0050 (10) | 0.0059 (10) | 0.0038 (10) |
C13 | 0.0358 (12) | 0.0420 (13) | 0.0414 (13) | 0.0036 (10) | 0.0024 (10) | −0.0050 (11) |
C14 | 0.0316 (11) | 0.0459 (13) | 0.0472 (13) | 0.0030 (10) | 0.0034 (10) | 0.0023 (11) |
C15 | 0.0424 (13) | 0.0533 (15) | 0.0428 (13) | 0.0017 (11) | 0.0073 (11) | −0.0014 (11) |
C16 | 0.0544 (15) | 0.0697 (18) | 0.0444 (14) | −0.0022 (14) | 0.0158 (12) | −0.0033 (13) |
S1—O2 | 1.4249 (18) | C4—H4A | 0.9300 |
S1—O3 | 1.4371 (19) | C5—C6 | 1.370 (3) |
S1—C6 | 1.724 (2) | C5—H5 | 0.9300 |
S1—C9 | 1.726 (2) | C6—C7 | 1.379 (3) |
O1—C1 | 1.390 (3) | C7—C8 | 1.342 (3) |
O1—H1 | 0.8200 | C7—H7 | 0.9300 |
O4—C16 | 1.402 (3) | C8—H8 | 0.9300 |
O4—H4 | 0.8200 | C9—C14 | 1.373 (3) |
N1—C3 | 1.343 (3) | C9—C10 | 1.379 (3) |
N1—C2 | 1.422 (3) | C10—C11 | 1.358 (3) |
N1—H1C | 0.892 (10) | C10—H10 | 0.9300 |
N2—C12 | 1.341 (3) | C11—C12 | 1.390 (3) |
N2—C15 | 1.429 (3) | C11—H11 | 0.9300 |
N2—H2C | 0.895 (10) | C12—C13 | 1.393 (3) |
C1—C2 | 1.494 (4) | C13—C14 | 1.356 (3) |
C1—H1A | 0.9700 | C13—H13 | 0.9300 |
C1—H1B | 0.9700 | C14—H14 | 0.9300 |
C2—H2A | 0.9700 | C15—C16 | 1.481 (3) |
C2—H2B | 0.9700 | C15—H15A | 0.9700 |
C3—C4 | 1.389 (3) | C15—H15B | 0.9700 |
C3—C8 | 1.396 (3) | C16—H16A | 0.9700 |
C4—C5 | 1.361 (3) | C16—H16B | 0.9700 |
O2—S1—O3 | 118.39 (11) | C7—C6—S1 | 119.89 (18) |
O2—S1—C6 | 108.63 (11) | C8—C7—C6 | 120.7 (2) |
O3—S1—C6 | 106.71 (11) | C8—C7—H7 | 119.7 |
O2—S1—C9 | 107.72 (11) | C6—C7—H7 | 119.7 |
O3—S1—C9 | 107.12 (11) | C7—C8—C3 | 121.0 (2) |
C6—S1—C9 | 107.85 (11) | C7—C8—H8 | 119.5 |
C1—O1—H1 | 109.5 | C3—C8—H8 | 119.5 |
C16—O4—H4 | 109.5 | C14—C9—C10 | 119.6 (2) |
C3—N1—C2 | 124.2 (2) | C14—C9—S1 | 119.16 (18) |
C3—N1—H1C | 114.2 (16) | C10—C9—S1 | 121.22 (18) |
C2—N1—H1C | 120.3 (16) | C11—C10—C9 | 120.0 (2) |
C12—N2—C15 | 123.6 (2) | C11—C10—H10 | 120.0 |
C12—N2—H2C | 115.9 (15) | C9—C10—H10 | 120.0 |
C15—N2—H2C | 119.8 (15) | C10—C11—C12 | 121.2 (2) |
O1—C1—C2 | 112.2 (2) | C10—C11—H11 | 119.4 |
O1—C1—H1A | 109.2 | C12—C11—H11 | 119.4 |
C2—C1—H1A | 109.2 | N2—C12—C11 | 119.9 (2) |
O1—C1—H1B | 109.2 | N2—C12—C13 | 122.2 (2) |
C2—C1—H1B | 109.2 | C11—C12—C13 | 117.9 (2) |
H1A—C1—H1B | 107.9 | C14—C13—C12 | 120.7 (2) |
N1—C2—C1 | 109.9 (2) | C14—C13—H13 | 119.7 |
N1—C2—H2A | 109.7 | C12—C13—H13 | 119.7 |
C1—C2—H2A | 109.7 | C13—C14—C9 | 120.7 (2) |
N1—C2—H2B | 109.7 | C13—C14—H14 | 119.7 |
C1—C2—H2B | 109.7 | C9—C14—H14 | 119.7 |
H2A—C2—H2B | 108.2 | N2—C15—C16 | 111.2 (2) |
N1—C3—C4 | 123.1 (2) | N2—C15—H15A | 109.4 |
N1—C3—C8 | 119.2 (2) | C16—C15—H15A | 109.4 |
C4—C3—C8 | 117.7 (2) | N2—C15—H15B | 109.4 |
C5—C4—C3 | 120.9 (2) | C16—C15—H15B | 109.4 |
C5—C4—H4A | 119.6 | H15A—C15—H15B | 108.0 |
C3—C4—H4A | 119.6 | O4—C16—C15 | 113.5 (2) |
C4—C5—C6 | 120.3 (2) | O4—C16—H16A | 108.9 |
C4—C5—H5 | 119.8 | C15—C16—H16A | 108.9 |
C6—C5—H5 | 119.8 | O4—C16—H16B | 108.9 |
C5—C6—C7 | 119.4 (2) | C15—C16—H16B | 108.9 |
C5—C6—S1 | 120.64 (18) | H16A—C16—H16B | 107.7 |
C3—N1—C2—C1 | −175.9 (2) | O2—S1—C9—C14 | 161.83 (17) |
O1—C1—C2—N1 | 60.4 (3) | O3—S1—C9—C14 | 33.5 (2) |
C2—N1—C3—C4 | −3.1 (3) | C6—S1—C9—C14 | −81.1 (2) |
C2—N1—C3—C8 | 176.8 (2) | O2—S1—C9—C10 | −20.3 (2) |
N1—C3—C4—C5 | −179.1 (2) | O3—S1—C9—C10 | −148.70 (18) |
C8—C3—C4—C5 | 1.0 (3) | C6—S1—C9—C10 | 96.8 (2) |
C3—C4—C5—C6 | −0.2 (3) | C14—C9—C10—C11 | −1.3 (3) |
C4—C5—C6—C7 | −0.4 (3) | S1—C9—C10—C11 | −179.14 (18) |
C4—C5—C6—S1 | 177.07 (17) | C9—C10—C11—C12 | 0.9 (3) |
O2—S1—C6—C5 | 37.3 (2) | C15—N2—C12—C11 | 177.4 (2) |
O3—S1—C6—C5 | 166.02 (17) | C15—N2—C12—C13 | −2.2 (3) |
C9—S1—C6—C5 | −79.2 (2) | C10—C11—C12—N2 | −179.1 (2) |
O2—S1—C6—C7 | −145.26 (17) | C10—C11—C12—C13 | 0.5 (3) |
O3—S1—C6—C7 | −16.6 (2) | N2—C12—C13—C14 | 178.0 (2) |
C9—S1—C6—C7 | 98.25 (19) | C11—C12—C13—C14 | −1.6 (3) |
C5—C6—C7—C8 | 0.0 (3) | C12—C13—C14—C9 | 1.2 (3) |
S1—C6—C7—C8 | −177.44 (17) | C10—C9—C14—C13 | 0.3 (3) |
C6—C7—C8—C3 | 0.9 (3) | S1—C9—C14—C13 | 178.15 (17) |
N1—C3—C8—C7 | 178.8 (2) | C12—N2—C15—C16 | −166.6 (2) |
C4—C3—C8—C7 | −1.4 (3) | N2—C15—C16—O4 | 61.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O3 | 0.93 | 2.59 | 2.919 (3) | 101 |
C10—H10···O2 | 0.93 | 2.57 | 2.915 (3) | 102 |
C7—H7···O3 | 0.93 | 2.47 | 2.854 (3) | 105 |
O1—H1···O3i | 0.82 | 1.87 | 2.683 (3) | 175 |
O1—H1···S1i | 0.82 | 2.88 | 3.638 (2) | 154 |
O4—H4···O2ii | 0.82 | 2.13 | 2.945 (3) | 177 |
N1—H1C···O4iii | 0.89 (1) | 2.19 (1) | 3.066 (3) | 169 (2) |
N2—H2C···O1iv | 0.90 (1) | 2.03 (1) | 2.917 (3) | 172 (2) |
C10—H10···Cg2v | 0.93 | 2.97 | 3.762 (4) | 144 |
Symmetry codes: (i) −x, y+1, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1/2, y+1/2, z; (iv) x+1/2, y−1/2, z; (v) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H20N2O4S |
Mr | 336.40 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 25.643 (17), 8.118 (6), 15.340 (11) |
β (°) | 102.989 (12) |
V (Å3) | 3112 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.20 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.953, 0.966 |
No. of measured, independent and observed (I > 2σ) reflections | 7793, 2742, 1982 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.110, 1.03 |
No. of reflections | 2742 |
No. of parameters | 218 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.35 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O3 | 0.93 | 2.59 | 2.919 (3) | 101.2 |
C10—H10···O2 | 0.93 | 2.57 | 2.915 (3) | 102.2 |
C7—H7···O3 | 0.93 | 2.47 | 2.854 (3) | 104.5 |
O1—H1···O3i | 0.82 | 1.87 | 2.683 (3) | 175.3 |
O1—H1···S1i | 0.82 | 2.88 | 3.638 (2) | 154.2 |
O4—H4···O2ii | 0.82 | 2.13 | 2.945 (3) | 176.8 |
N1—H1C···O4iii | 0.892 (10) | 2.185 (11) | 3.066 (3) | 169 (2) |
N2—H2C···O1iv | 0.895 (10) | 2.027 (11) | 2.917 (3) | 172 (2) |
C10—H10···Cg2v | 0.93 | 2.97 | 3.762 (4) | 144.00 |
Symmetry codes: (i) −x, y+1, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1/2, y+1/2, z; (iv) x+1/2, y−1/2, z; (v) −x+1/2, y+1/2, −z+1/2. |
References
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Shahsafi, M. A., Meshkatalsadat, M. H. & Parekh, H. (1987). Indian J. Chem. 26B, 803–807. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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The derivatives of diphenyl sulphone are used as precursors in the organic synthesis. Several derivatives of aminosulphones have been shown to possess strong tuberculostatic, antileprotic and anticonvulsant activities (Shahsafi, et al., 1987). The crystal structure determination of the title compound, (I), was carried out in order to elucidate its molecular conformation.
The V-shape structure of the molecule is supported by the two phenyl rings with a dihedral angle of 77.5 (11)°.
The molecular packing is stabilized by intramolecular and intermolecular hydrogen bonds (Table 1) as well as weak π-π and C—H..π interactions.