organic compounds
{2-[(2-Hydroxybenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}(phenyl)methanone
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cMaterials Science Center, University of Mysore, Vijyana Bhavan Building, Manasagangothri, Mysore 570 006, India
*Correspondence e-mail: jjasinski@keene.edu
In the title compound, C22H19NO2S, the cyclohexene ring adopts a slightly distorted half-chair conformation. The dihedral angles between the mean planes of the thiophene ring and the phenyl and 2-hydroxyphenyl rings are 70.4 (5) and 12.1 (9)°, respectively. The phenyl and 2-hydroxyphenyl rings are twisted with respect to one another by 81.0 (6)°. A short intramolecular O—H⋯N hydrogen bond is observed. In the crystal, weak C—H⋯O interactions link the molecules into zigzag chains diagonally along [100] .
CCDC reference: 992723
Related literature
For the importance of thiophene derivatives, see: Molvi et al. (2007); Rai et al. (2008); Asthalatha et al. (2007). For applications of 2-aminothiophene derivatives, see: Sabnis et al. (1999); Puterová et al. (2010); Cannito et al. (1990); Nikolakopoulos et al. (2006); Lütjens et al. (2005). For the biological and industrial importance of see: Desai et al. (2001); Karia & Parsania (1999); Samadhiya & Halve (2001); Singh & Dash (1988); Aydogan et al. (2001); Taggi et al. (2002). For a related structure, see: Kubicki et al. (2012). For puckering parameters, see Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 992723
10.1107/S1600536814006199/sj5393sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814006199/sj5393Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814006199/sj5393Isup3.cml
To a solution of (2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)- phenyl-methanone (200 mg, 0.79 mmol) in 10 ml of methanol an equimolar amount of 2-hydroxybenzaldehyde (97 mg, 0.79 mmol) was added dropwise with constant stirring. The mixture was refluxed for 3 hours. A yellow precipitate was obtained. The reaction completion was confirmed by thin layer
The resulting precipitate was filtered and dried at room temperature overnight. The solid was recrystallized from dichloromethane and the crystals were used as such for x-ray diffraction studies.All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93Å (CH); 0.99Å (CH2) or 0.82Å (OH). Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2) or 1.5 (OH) times Ueq of the parent atom. The idealised tetrahedral OH was refined as a rotating group.
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C22H19NO2S | F(000) = 760 |
Mr = 361.44 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 9.26395 (15) Å | Cell parameters from 5377 reflections |
b = 14.2886 (2) Å | θ = 4.5–71.3° |
c = 13.6476 (2) Å | µ = 1.73 mm−1 |
β = 96.7581 (15)° | T = 173 K |
V = 1793.97 (5) Å3 | Block, yellow |
Z = 4 | 0.24 × 0.14 × 0.08 mm |
Agilent Eos Gemini diffractometer | 3462 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3113 reflections with I > 2σ(I) |
Detector resolution: 16.0416 pixels mm-1 | Rint = 0.053 |
ω scans | θmax = 71.5°, θmin = 4.5° |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | h = −11→10 |
Tmin = 0.658, Tmax = 1.000 | k = −17→17 |
11611 measured reflections | l = −16→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.0863P)2 + 0.6814P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.142 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 1.03 e Å−3 |
3462 reflections | Δρmin = −0.26 e Å−3 |
237 parameters | Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0024 (4) |
Primary atom site location: structure-invariant direct methods |
C22H19NO2S | V = 1793.97 (5) Å3 |
Mr = 361.44 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 9.26395 (15) Å | µ = 1.73 mm−1 |
b = 14.2886 (2) Å | T = 173 K |
c = 13.6476 (2) Å | 0.24 × 0.14 × 0.08 mm |
β = 96.7581 (15)° |
Agilent Eos Gemini diffractometer | 3462 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | 3113 reflections with I > 2σ(I) |
Tmin = 0.658, Tmax = 1.000 | Rint = 0.053 |
11611 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.06 | Δρmax = 1.03 e Å−3 |
3462 reflections | Δρmin = −0.26 e Å−3 |
237 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.55854 (5) | 0.11521 (3) | 0.69557 (3) | 0.02933 (18) | |
O1 | 0.74691 (15) | 0.17574 (10) | 0.38642 (9) | 0.0336 (3) | |
O2 | 0.69355 (16) | 0.45879 (10) | 0.56596 (11) | 0.0364 (4) | |
H2 | 0.6928 | 0.4014 | 0.5663 | 0.055* | |
N1 | 0.61684 (16) | 0.29064 (11) | 0.62125 (11) | 0.0259 (3) | |
C1 | 0.77920 (18) | 0.19624 (12) | 0.47290 (13) | 0.0243 (4) | |
C2 | 0.70603 (18) | 0.14805 (12) | 0.55066 (13) | 0.0248 (4) | |
C3 | 0.70100 (18) | 0.04840 (12) | 0.56039 (13) | 0.0255 (4) | |
C4 | 0.7719 (2) | −0.02126 (13) | 0.49863 (15) | 0.0312 (4) | |
H4A | 0.8641 | 0.0034 | 0.4832 | 0.037* | |
H4B | 0.7103 | −0.0316 | 0.4370 | 0.037* | |
C5 | 0.7967 (3) | −0.11336 (16) | 0.5535 (2) | 0.0470 (6) | |
H5A | 0.8254 | −0.1606 | 0.5086 | 0.056* | |
H5B | 0.8757 | −0.1059 | 0.6063 | 0.056* | |
C6 | 0.6632 (3) | −0.14608 (16) | 0.5964 (2) | 0.0502 (6) | |
H6A | 0.6840 | −0.2058 | 0.6288 | 0.060* | |
H6B | 0.5858 | −0.1560 | 0.5430 | 0.060* | |
C7 | 0.6102 (2) | −0.07799 (14) | 0.67023 (15) | 0.0340 (4) | |
H7A | 0.5088 | −0.0902 | 0.6767 | 0.041* | |
H7B | 0.6658 | −0.0868 | 0.7344 | 0.041* | |
C8 | 0.62751 (19) | 0.02115 (12) | 0.63622 (14) | 0.0271 (4) | |
C9 | 0.63331 (18) | 0.19440 (12) | 0.61848 (13) | 0.0249 (4) | |
C10 | 0.89550 (18) | 0.26513 (12) | 0.50409 (13) | 0.0243 (4) | |
C11 | 0.9396 (2) | 0.32721 (14) | 0.43438 (13) | 0.0304 (4) | |
H11 | 0.8930 | 0.3271 | 0.3702 | 0.036* | |
C12 | 1.0525 (2) | 0.38872 (15) | 0.46073 (15) | 0.0364 (5) | |
H12 | 1.0806 | 0.4307 | 0.4145 | 0.044* | |
C13 | 1.1242 (2) | 0.38818 (15) | 0.55585 (16) | 0.0369 (5) | |
H13 | 1.2010 | 0.4292 | 0.5730 | 0.044* | |
C14 | 1.0813 (2) | 0.32637 (16) | 0.62539 (14) | 0.0345 (4) | |
H14 | 1.1297 | 0.3257 | 0.6891 | 0.041* | |
C15 | 0.96629 (19) | 0.26566 (14) | 0.59984 (13) | 0.0291 (4) | |
H15 | 0.9364 | 0.2252 | 0.6468 | 0.035* | |
C16 | 0.52973 (19) | 0.33090 (13) | 0.67519 (14) | 0.0272 (4) | |
H16 | 0.4764 | 0.2942 | 0.7143 | 0.033* | |
C17 | 0.51257 (19) | 0.43151 (13) | 0.67668 (13) | 0.0261 (4) | |
C18 | 0.4120 (2) | 0.47131 (14) | 0.73438 (14) | 0.0309 (4) | |
H18 | 0.3603 | 0.4329 | 0.7728 | 0.037* | |
C19 | 0.3894 (2) | 0.56679 (15) | 0.73455 (15) | 0.0359 (5) | |
H19 | 0.3225 | 0.5924 | 0.7727 | 0.043* | |
C20 | 0.4668 (2) | 0.62451 (14) | 0.67759 (16) | 0.0361 (5) | |
H20 | 0.4501 | 0.6887 | 0.6769 | 0.043* | |
C21 | 0.5681 (2) | 0.58765 (14) | 0.62214 (16) | 0.0355 (4) | |
H21 | 0.6205 | 0.6271 | 0.5852 | 0.043* | |
C22 | 0.5925 (2) | 0.49131 (13) | 0.62120 (14) | 0.0281 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0347 (3) | 0.0245 (3) | 0.0310 (3) | −0.00448 (16) | 0.01296 (19) | −0.00091 (16) |
O1 | 0.0390 (7) | 0.0356 (8) | 0.0264 (7) | −0.0060 (6) | 0.0048 (5) | −0.0032 (5) |
O2 | 0.0406 (8) | 0.0252 (7) | 0.0470 (8) | −0.0044 (6) | 0.0205 (6) | −0.0017 (6) |
N1 | 0.0265 (7) | 0.0222 (7) | 0.0295 (8) | −0.0025 (6) | 0.0055 (6) | −0.0010 (6) |
C1 | 0.0241 (8) | 0.0230 (8) | 0.0260 (8) | 0.0024 (6) | 0.0046 (6) | 0.0006 (7) |
C2 | 0.0220 (8) | 0.0239 (9) | 0.0284 (9) | −0.0022 (7) | 0.0027 (6) | −0.0012 (7) |
C3 | 0.0225 (8) | 0.0228 (8) | 0.0309 (9) | −0.0020 (6) | 0.0017 (7) | −0.0018 (7) |
C4 | 0.0310 (9) | 0.0273 (9) | 0.0359 (10) | 0.0022 (7) | 0.0063 (7) | −0.0044 (8) |
C5 | 0.0515 (13) | 0.0336 (12) | 0.0557 (14) | 0.0093 (9) | 0.0060 (11) | −0.0040 (9) |
C6 | 0.0622 (15) | 0.0241 (10) | 0.0659 (16) | −0.0026 (10) | 0.0144 (12) | −0.0007 (10) |
C7 | 0.0365 (10) | 0.0248 (9) | 0.0407 (11) | −0.0068 (8) | 0.0042 (8) | 0.0043 (8) |
C8 | 0.0277 (9) | 0.0215 (9) | 0.0322 (9) | −0.0019 (7) | 0.0034 (7) | −0.0023 (7) |
C9 | 0.0251 (8) | 0.0234 (9) | 0.0266 (8) | −0.0039 (7) | 0.0047 (6) | 0.0002 (7) |
C10 | 0.0230 (8) | 0.0255 (9) | 0.0255 (8) | 0.0007 (7) | 0.0067 (6) | −0.0001 (7) |
C11 | 0.0321 (9) | 0.0353 (10) | 0.0238 (8) | −0.0046 (8) | 0.0041 (7) | 0.0038 (7) |
C12 | 0.0396 (11) | 0.0389 (11) | 0.0319 (10) | −0.0114 (8) | 0.0097 (8) | 0.0040 (8) |
C13 | 0.0311 (10) | 0.0429 (12) | 0.0372 (11) | −0.0131 (8) | 0.0064 (8) | −0.0058 (8) |
C14 | 0.0297 (9) | 0.0467 (12) | 0.0266 (9) | −0.0043 (8) | 0.0016 (7) | −0.0025 (8) |
C15 | 0.0281 (9) | 0.0347 (10) | 0.0253 (9) | −0.0013 (7) | 0.0060 (7) | 0.0028 (7) |
C16 | 0.0271 (8) | 0.0250 (9) | 0.0303 (9) | −0.0034 (7) | 0.0063 (7) | −0.0006 (7) |
C17 | 0.0246 (8) | 0.0245 (9) | 0.0288 (9) | −0.0011 (7) | 0.0008 (7) | −0.0033 (7) |
C18 | 0.0301 (9) | 0.0309 (10) | 0.0320 (9) | −0.0011 (7) | 0.0051 (7) | −0.0033 (7) |
C19 | 0.0351 (10) | 0.0345 (10) | 0.0381 (10) | 0.0081 (8) | 0.0043 (8) | −0.0079 (8) |
C20 | 0.0435 (11) | 0.0239 (9) | 0.0393 (11) | 0.0051 (8) | −0.0021 (8) | −0.0044 (8) |
C21 | 0.0428 (11) | 0.0259 (10) | 0.0378 (10) | −0.0047 (8) | 0.0047 (8) | 0.0006 (8) |
C22 | 0.0287 (9) | 0.0255 (9) | 0.0300 (9) | −0.0029 (7) | 0.0027 (7) | −0.0036 (7) |
S1—C8 | 1.7299 (18) | C7—C8 | 1.505 (3) |
S1—C9 | 1.7432 (18) | C10—C11 | 1.397 (3) |
O1—C1 | 1.219 (2) | C10—C15 | 1.392 (3) |
O2—H2 | 0.8200 | C11—H11 | 0.9300 |
O2—C22 | 1.351 (2) | C11—C12 | 1.381 (3) |
N1—C9 | 1.385 (2) | C12—H12 | 0.9300 |
N1—C16 | 1.290 (2) | C12—C13 | 1.387 (3) |
C1—C2 | 1.493 (2) | C13—H13 | 0.9300 |
C1—C10 | 1.484 (2) | C13—C14 | 1.388 (3) |
C2—C3 | 1.431 (2) | C14—H14 | 0.9300 |
C2—C9 | 1.377 (2) | C14—C15 | 1.386 (3) |
C3—C4 | 1.504 (2) | C15—H15 | 0.9300 |
C3—C8 | 1.361 (3) | C16—H16 | 0.9300 |
C4—H4A | 0.9700 | C16—C17 | 1.447 (3) |
C4—H4B | 0.9700 | C17—C18 | 1.409 (3) |
C4—C5 | 1.518 (3) | C17—C22 | 1.409 (3) |
C5—H5A | 0.9700 | C18—H18 | 0.9300 |
C5—H5B | 0.9700 | C18—C19 | 1.380 (3) |
C5—C6 | 1.504 (4) | C19—H19 | 0.9300 |
C6—H6A | 0.9700 | C19—C20 | 1.390 (3) |
C6—H6B | 0.9700 | C20—H20 | 0.9300 |
C6—C7 | 1.523 (3) | C20—C21 | 1.378 (3) |
C7—H7A | 0.9700 | C21—H21 | 0.9300 |
C7—H7B | 0.9700 | C21—C22 | 1.395 (3) |
C8—S1—C9 | 91.53 (9) | C2—C9—N1 | 124.08 (16) |
C22—O2—H2 | 109.5 | C11—C10—C1 | 119.12 (16) |
C16—N1—C9 | 122.47 (15) | C15—C10—C1 | 121.26 (16) |
O1—C1—C2 | 119.82 (16) | C15—C10—C11 | 119.53 (17) |
O1—C1—C10 | 121.62 (16) | C10—C11—H11 | 120.0 |
C10—C1—C2 | 118.49 (15) | C12—C11—C10 | 120.01 (18) |
C3—C2—C1 | 123.18 (15) | C12—C11—H11 | 120.0 |
C9—C2—C1 | 123.70 (16) | C11—C12—H12 | 119.8 |
C9—C2—C3 | 113.09 (16) | C11—C12—C13 | 120.33 (18) |
C2—C3—C4 | 125.81 (16) | C13—C12—H12 | 119.8 |
C8—C3—C2 | 112.33 (16) | C12—C13—H13 | 120.0 |
C8—C3—C4 | 121.83 (17) | C12—C13—C14 | 119.94 (18) |
C3—C4—H4A | 109.6 | C14—C13—H13 | 120.0 |
C3—C4—H4B | 109.6 | C13—C14—H14 | 120.0 |
C3—C4—C5 | 110.36 (17) | C15—C14—C13 | 119.98 (18) |
H4A—C4—H4B | 108.1 | C15—C14—H14 | 120.0 |
C5—C4—H4A | 109.6 | C10—C15—H15 | 119.9 |
C5—C4—H4B | 109.6 | C14—C15—C10 | 120.19 (17) |
C4—C5—H5A | 109.2 | C14—C15—H15 | 119.9 |
C4—C5—H5B | 109.2 | N1—C16—H16 | 119.1 |
H5A—C5—H5B | 107.9 | N1—C16—C17 | 121.89 (16) |
C6—C5—C4 | 112.2 (2) | C17—C16—H16 | 119.1 |
C6—C5—H5A | 109.2 | C18—C17—C16 | 119.34 (17) |
C6—C5—H5B | 109.2 | C22—C17—C16 | 121.99 (16) |
C5—C6—H6A | 108.8 | C22—C17—C18 | 118.67 (17) |
C5—C6—H6B | 108.8 | C17—C18—H18 | 119.7 |
C5—C6—C7 | 113.75 (19) | C19—C18—C17 | 120.70 (18) |
H6A—C6—H6B | 107.7 | C19—C18—H18 | 119.7 |
C7—C6—H6A | 108.8 | C18—C19—H19 | 120.1 |
C7—C6—H6B | 108.8 | C18—C19—C20 | 119.81 (18) |
C6—C7—H7A | 109.6 | C20—C19—H19 | 120.1 |
C6—C7—H7B | 109.6 | C19—C20—H20 | 119.7 |
H7A—C7—H7B | 108.2 | C21—C20—C19 | 120.70 (18) |
C8—C7—C6 | 110.05 (17) | C21—C20—H20 | 119.7 |
C8—C7—H7A | 109.6 | C20—C21—H21 | 119.9 |
C8—C7—H7B | 109.6 | C20—C21—C22 | 120.24 (19) |
C3—C8—S1 | 112.29 (14) | C22—C21—H21 | 119.9 |
C3—C8—C7 | 125.78 (17) | O2—C22—C17 | 122.26 (17) |
C7—C8—S1 | 121.89 (14) | O2—C22—C21 | 117.89 (17) |
N1—C9—S1 | 125.12 (13) | C21—C22—C17 | 119.85 (18) |
C2—C9—S1 | 110.74 (13) | ||
O1—C1—C2—C3 | 53.9 (2) | C8—C3—C4—C5 | −20.5 (3) |
O1—C1—C2—C9 | −124.32 (19) | C9—S1—C8—C3 | −1.22 (14) |
O1—C1—C10—C11 | 18.8 (3) | C9—S1—C8—C7 | 176.49 (16) |
O1—C1—C10—C15 | −157.73 (17) | C9—N1—C16—C17 | −179.41 (16) |
N1—C16—C17—C18 | 177.77 (17) | C9—C2—C3—C4 | −178.91 (16) |
N1—C16—C17—C22 | −1.6 (3) | C9—C2—C3—C8 | −1.2 (2) |
C1—C2—C3—C4 | 2.7 (3) | C10—C1—C2—C3 | −123.18 (18) |
C1—C2—C3—C8 | −179.58 (16) | C10—C1—C2—C9 | 58.6 (2) |
C1—C2—C9—S1 | 178.63 (13) | C10—C11—C12—C13 | 1.1 (3) |
C1—C2—C9—N1 | 1.4 (3) | C11—C10—C15—C14 | −1.0 (3) |
C1—C10—C11—C12 | −176.81 (18) | C11—C12—C13—C14 | −0.8 (3) |
C1—C10—C15—C14 | 175.54 (17) | C12—C13—C14—C15 | −0.4 (3) |
C2—C1—C10—C11 | −164.18 (16) | C13—C14—C15—C10 | 1.3 (3) |
C2—C1—C10—C15 | 19.2 (2) | C15—C10—C11—C12 | −0.2 (3) |
C2—C3—C4—C5 | 156.98 (18) | C16—N1—C9—S1 | −7.9 (3) |
C2—C3—C8—S1 | 1.60 (19) | C16—N1—C9—C2 | 168.92 (17) |
C2—C3—C8—C7 | −176.01 (17) | C16—C17—C18—C19 | −177.65 (17) |
C3—C2—C9—S1 | 0.30 (19) | C16—C17—C22—O2 | −2.3 (3) |
C3—C2—C9—N1 | −176.90 (16) | C16—C17—C22—C21 | 177.57 (17) |
C3—C4—C5—C6 | 48.4 (3) | C17—C18—C19—C20 | −0.3 (3) |
C4—C3—C8—S1 | 179.39 (13) | C18—C17—C22—O2 | 178.33 (17) |
C4—C3—C8—C7 | 1.8 (3) | C18—C17—C22—C21 | −1.8 (3) |
C4—C5—C6—C7 | −60.2 (3) | C18—C19—C20—C21 | −1.2 (3) |
C5—C6—C7—C8 | 38.5 (3) | C19—C20—C21—C22 | 1.1 (3) |
C6—C7—C8—S1 | 172.38 (16) | C20—C21—C22—O2 | −179.69 (18) |
C6—C7—C8—C3 | −10.2 (3) | C20—C21—C22—C17 | 0.4 (3) |
C8—S1—C9—N1 | 177.66 (16) | C22—C17—C18—C19 | 1.7 (3) |
C8—S1—C9—C2 | 0.50 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1 | 0.82 | 1.92 | 2.641 (2) | 146 |
C18—H18···O1i | 0.93 | 2.51 | 3.436 (2) | 174 |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1 | 0.82 | 1.92 | 2.641 (2) | 146.2 |
C18—H18···O1i | 0.93 | 2.51 | 3.436 (2) | 173.8 |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
Acknowledgements
MK is grateful to the CPEPA–UGC for the award of a JRF and thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
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Thiophene derivatives have been reported to exhibit a broad spectrum of biological properties such as anti-inflammatory, analgesic, antidepressant, antimicrobial and anticonvulsant activities (Molvi et al., 2007; Rai et al., 2008; Asthalatha et al. , 2007). 2-Aminothiophene derivatives have been used in a number of applications as pesticides, dyes and pharmaceuticals. Reviews of the synthesis and properties of these compounds have been reported (Sabnis et al. 1999; Puterová et al. 2010). Substituted 2-aminothiophenes are active as allosteric enhancers at the human A1 adenosine receptor (Cannito et al.,1990; Nikolakopoulos et al., 2006; Lütjens et al., 2005). Schiff base compounds are an important class of compounds both synthetically and biologically. These compounds also show biological activities including antibacterial, antifungal, anticancer and herbicidal activities (Desai et al., 2001; Karia & Parsania, 1999; Samadhiya & Halve, 2001; Singh & Dash, 1988). Furthermore, Schiff bases are utilized as starting materials in the synthesis of compounds of industrial (Aydogan et al., 2001) and biological interest such as β-lactams (Taggi et al., 2002). The crystal and molecular structures of two 2-aminothiphenes have been previously reported by our group (Kubicki et al., 2012). In continuation of our work on 2-aminothiophenes and Schiff bases, we report here the crystal structure of the title compound, (I), C22H19NO2S.
In the title compound, (I), the cyclohexene ring adopts a slightly distorted half-chair conformation (puckering parameters Q, θ, and ϕ = 0.459 (3)Å, 48.9 (2)° and 138.1 (4)°, respectively; Cremer & Pople, 1975) (Fig. 1). The dihedral angles between the mean planes of the thiophene and phenyl rings and the 2-hydroxyphenyl ring are 70.4 (5)° and 12.1 (9)°, respectively. The phenyl and the 2-hydroxyphenyl rings are twisted with respect to each other by 81.0 (6)°. Bond lengths are in normal ranges (Allen et al., 1987). A short intramolecular O2—H2···N1 hydrogen bond is observed. In the crystal, a single weak intermolecular C18–H18···O1 interaction links the molecules into zig-zag chains along [101] which influences the crystal packing (Fig. 2).