Literature DB >> 21577977

(2E)-1-(4-Amino-phen-yl)-3-(2-thien-yl)prop-2-en-1-one ethanol hemisolvate.

Hoong-Kun Fun, Thawanrat Kobkeatthawin, Suchada Chantrapromma.   

Abstract

In the title compound, C(13)H(11)NOS·0.5C(2)H(6)O, the chalcone derivative is close to planar, the dihedral angle between the thio-phene and 4-amino-phenyl rings being 3.1 (2)°. The thio-phene ring is disordered over two orientations with occupancies of 0.842 (3) and 0.158 (3). In the crystal structure, mol-ecules are linked into chains along the b axis by N-H⋯O hydrogen bonds. The chains are crosslinked via N-H⋯π inter-actions involving the thio-phene ring. The ethanol solvent mol-ecule is also disordered over two positions, each with an occupancy of 0.25.

Entities:  

Year:  2009        PMID： 21577977      PMCID： PMC2970323          DOI： 10.1107/S1600536809037933

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2009 ▶); Suwunwong et al. (2009 ▶). For background and applications of chalcones, see: Dimmock et al. (1999 ▶); Go et al. (2005 ▶); Ni et al. (2004 ▶); Patil & Dharmaprakash (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H11NOS·0.5C2H6O M = 252.32 Orthorhombic, a = 5.1413 (1) Å b = 13.9754 (2) Å c = 18.2647 (2) Å V = 1312.35 (3) Å3 Z = 4 Mo Kα radiation μ = 0.24 mm−1 T = 100 K 0.56 × 0.22 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.879, T max = 0.961 22258 measured reflections 4225 independent reflections 3893 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.061 wR(F 2) = 0.205 S = 1.09 4225 reflections 188 parameters 14 restraints H-atom parameters constrained Δρmax = 1.04 e Å−3 Δρmin = −0.31 e Å−3 Absolute structure: Flack (1983 ▶), 1874 Friedel pairs Flack parameter: 0.00 (12) Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037933/ci2908sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037933/ci2908Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H11NOS·0.5C2H6ODx = 1.277 Mg m−3
Mr = 252.32Melting point = 378–379 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4225 reflections
a = 5.1413 (1) Åθ = 1.8–31.1°
b = 13.9754 (2) ŵ = 0.24 mm−1
c = 18.2647 (2) ÅT = 100 K
V = 1312.35 (3) Å3Plate, yellow
Z = 40.56 × 0.22 × 0.17 mm
F(000) = 532
Bruker APEXII CCD area-detector diffractometer4225 independent reflections
Radiation source: sealed tube3893 reflections with I > 2σ(I)
graphiteRint = 0.026
φ and ω scansθmax = 31.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −7→7
Tmin = 0.879, Tmax = 0.961k = −20→15
22258 measured reflectionsl = −26→24
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.205w = 1/[σ2(Fo2) + (0.1552P)2 + 0.2319P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
4225 reflectionsΔρmax = 1.04 e Å−3
188 parametersΔρmin = −0.31 e Å−3
14 restraintsAbsolute structure: Flack (1983), 1874 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.00 (12)
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.
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.
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.
xyzUiso*/UeqOcc. (<1)
O10.4331 (4)−0.19026 (12)0.23694 (11)0.0354 (4)
N1−0.3267 (4)0.13702 (15)0.34900 (11)0.0303 (4)
H1A−0.33110.19710.33900.036*
H1B−0.43250.11350.38070.036*
C10.0494 (4)−0.07627 (15)0.29945 (11)0.0260 (4)
H10.0568−0.14080.31160.031*
C2−0.1363 (4)−0.01898 (16)0.33217 (11)0.0257 (4)
H2−0.2512−0.04530.36590.031*
C3−0.1526 (4)0.07911 (15)0.31464 (11)0.0249 (4)
C40.0225 (5)0.11577 (16)0.26252 (12)0.0296 (4)
H40.01350.18000.24950.035*
C50.2078 (4)0.05764 (16)0.23027 (13)0.0284 (4)
H50.32140.08350.19600.034*
C60.2273 (4)−0.03956 (15)0.24835 (10)0.0232 (4)
C70.4185 (4)−0.10551 (15)0.21554 (11)0.0244 (4)
C80.5911 (4)−0.07082 (15)0.15699 (12)0.0256 (4)
H80.5733−0.00820.14050.031*
C90.7742 (4)−0.12715 (15)0.12666 (11)0.0251 (4)
H90.7867−0.18970.14360.030*
C100.9527 (4)−0.09779 (15)0.06978 (11)0.0241 (4)
S10.95430 (16)0.01724 (6)0.03611 (4)0.0312 (2)0.842 (3)
C111.2101 (13)−0.0077 (4)−0.0214 (2)0.0304 (8)0.842 (3)
H111.28480.0368−0.05290.037*0.842 (3)
C121.2907 (12)−0.1014 (4)−0.0157 (4)0.0293 (6)0.842 (3)
H121.4268−0.1277−0.04250.035*0.842 (3)
C131.1404 (12)−0.1509 (4)0.0372 (4)0.0291 (11)0.842 (3)
H131.1694−0.21500.04810.035*0.842 (3)
S1A1.1592 (16)−0.1790 (5)0.0320 (5)0.0257 (13)0.158 (3)
C11A1.312 (7)−0.095 (2)−0.020 (2)0.0293 (6)0.16
H11A1.4432−0.1078−0.05360.035*0.158 (3)
C12A1.208 (7)−0.006 (2)−0.0088 (18)0.0304 (8)0.16
H12A1.25130.0496−0.03410.037*0.158 (3)
C13A1.005 (4)−0.0026 (14)0.0424 (12)0.0291 (11)0.16
H13A0.92940.05170.06280.035*0.158 (3)
O2−0.2058 (19)−0.2501 (8)0.4350 (6)0.060 (3)*0.25
H2B−0.3410−0.23680.45650.089*0.25
C140.013 (2)−0.2424 (15)0.4817 (8)0.070 (4)*0.25
H14A0.0016−0.29510.51610.084*0.25
H14B0.0012−0.18320.50930.084*0.25
C150.272 (2)−0.2486 (12)0.4437 (9)0.058 (3)*0.25
H15A0.3970−0.27930.47480.087*0.25
H15B0.3290−0.18480.43280.087*0.25
H15C0.2548−0.28420.39900.087*0.25
O2A0.333 (2)−0.2650 (10)0.4138 (7)0.075 (3)*0.25
H2AA0.3521−0.25360.37000.113*0.25
C14A0.059 (3)−0.2529 (15)0.4304 (7)0.070 (4)*0.25
H14C−0.0254−0.28590.39090.084*0.25
H14D0.0526−0.18700.41580.084*0.25
C15A0.012 (3)−0.2491 (14)0.5119 (7)0.064 (4)*0.25
H15G−0.1703−0.24130.52180.096*0.25
H15D0.0720−0.30780.53330.096*0.25
H15E0.1065−0.19630.53240.096*0.25
U11U22U33U12U13U23
O10.0388 (9)0.0271 (7)0.0402 (9)−0.0006 (7)0.0127 (8)−0.0014 (6)
N10.0301 (9)0.0343 (9)0.0266 (8)0.0049 (7)0.0037 (7)−0.0008 (7)
C10.0271 (9)0.0298 (9)0.0211 (8)−0.0024 (8)0.0010 (7)0.0000 (7)
C20.0262 (8)0.0299 (9)0.0210 (8)−0.0017 (8)0.0025 (7)−0.0004 (7)
C30.0232 (8)0.0309 (9)0.0207 (8)−0.0009 (7)−0.0029 (7)−0.0030 (7)
C40.0300 (10)0.0293 (9)0.0295 (10)0.0002 (8)0.0042 (8)0.0015 (8)
C50.0260 (9)0.0317 (10)0.0275 (9)−0.0011 (8)0.0057 (8)−0.0003 (8)
C60.0227 (8)0.0274 (9)0.0194 (8)−0.0032 (7)−0.0006 (6)−0.0045 (6)
C70.0228 (9)0.0271 (8)0.0234 (9)−0.0036 (7)0.0010 (7)−0.0033 (7)
C80.0233 (9)0.0317 (9)0.0217 (8)−0.0027 (7)0.0019 (7)−0.0016 (7)
C90.0221 (8)0.0294 (9)0.0237 (9)−0.0041 (7)−0.0008 (7)−0.0007 (7)
C100.0209 (8)0.0298 (8)0.0216 (8)−0.0026 (7)−0.0017 (7)−0.0006 (7)
S10.0333 (4)0.0323 (4)0.0279 (3)0.0023 (3)0.0062 (3)0.0037 (3)
C110.0314 (11)0.0398 (12)0.020 (2)−0.0038 (9)0.0043 (14)0.0031 (14)
C120.0222 (15)0.0416 (14)0.0243 (13)−0.0012 (10)0.0021 (10)0.0018 (10)
C130.0248 (16)0.033 (2)0.0298 (17)0.0007 (17)−0.0037 (12)−0.0028 (19)
S1A0.0227 (19)0.031 (3)0.023 (2)−0.003 (2)0.0025 (15)0.003 (2)
C11A0.0222 (15)0.0416 (14)0.0243 (13)−0.0012 (10)0.0021 (10)0.0018 (10)
C12A0.0314 (11)0.0398 (12)0.020 (2)−0.0038 (9)0.0043 (14)0.0031 (14)
C13A0.0248 (16)0.033 (2)0.0298 (17)0.0007 (17)−0.0037 (12)−0.0028 (19)
O1—C71.250 (3)C11—H110.93
N1—C31.360 (3)C12—C131.418 (8)
N1—H1A0.86C12—H120.93
N1—H1B0.86C13—H130.93
C1—C21.382 (3)S1A—C11A1.70 (2)
C1—C61.404 (3)C11A—C12A1.373 (17)
C1—H10.93C11A—H11A0.93
C2—C31.410 (3)C12A—C13A1.40 (2)
C2—H20.93C12A—H12A0.93
C3—C41.407 (3)C13A—H13A0.93
C4—C51.384 (3)O2—C141.416 (9)
C4—H40.93O2—H2B0.82
C5—C61.402 (3)C14—C151.504 (10)
C5—H50.93C14—H14A0.97
C6—C71.475 (3)C14—H14B0.97
C7—C81.472 (3)C15—H15A0.96
C8—C91.346 (3)C15—H15B0.96
C8—H80.93C15—H15C0.96
C9—C101.446 (3)O2A—C14A1.449 (9)
C9—H90.93O2A—H2AA0.82
C10—C131.355 (6)C14A—C15A1.509 (9)
C10—C13A1.45 (2)C14A—H14C0.96
C10—S1A1.701 (8)C14A—H14D0.96
C10—S11.721 (2)C15A—H15G0.96
S1—C111.719 (5)C15A—H15D0.96
C11—C121.377 (5)C15A—H15E0.96
C3—N1—H1A120.0C11—C12—H12124.2
C3—N1—H1B120.0C13—C12—H12125.2
H1A—N1—H1B120.0C10—C13—C12114.8 (5)
C2—C1—C6121.7 (2)C10—C13—H13123.3
C2—C1—H1119.1C12—C13—H13121.9
C6—C1—H1119.1C11A—S1A—C1093.1 (12)
C1—C2—C3120.41 (19)C12A—C11A—S1A111 (2)
C1—C2—H2119.8C12A—C11A—H11A123.4
C3—C2—H2119.8S1A—C11A—H11A125.1
N1—C3—C4121.1 (2)C11A—C12A—H12A126.4
N1—C3—C2120.8 (2)C13A—C12A—H12A118.7
C4—C3—C2118.0 (2)C12A—C13A—C10109.7 (16)
C5—C4—C3121.0 (2)C12A—C13A—H13A127.1
C5—C4—H4119.5C10—C13A—H13A122.4
C3—C4—H4119.5C14—O2—H2B111.5
C4—C5—C6121.2 (2)O2—C14—C15114.9 (10)
C4—C5—H5119.4O2—C14—H14A106.6
C6—C5—H5119.4C15—C14—H14A108.0
C5—C6—C1117.7 (2)O2—C14—H14B109.2
C5—C6—C7123.89 (19)C15—C14—H14B110.1
C1—C6—C7118.42 (19)H14A—C14—H14B107.9
O1—C7—C8120.21 (19)C14—C15—H15A110.2
O1—C7—C6120.36 (19)C14—C15—H15B108.2
C8—C7—C6119.43 (18)H15A—C15—H15B109.5
C9—C8—C7121.9 (2)C14—C15—H15C109.9
C9—C8—H8119.1H15A—C15—H15C109.5
C7—C8—H8119.1H15B—C15—H15C109.5
C8—C9—C10125.0 (2)C14A—O2A—H2AA107.3
C8—C9—H9117.5O2A—C14A—C15A111.5 (9)
C10—C9—H9117.5O2A—C14A—H14C103.1
C13—C10—C9127.7 (3)C15A—C14A—H14C133.2
C13A—C10—C9128.8 (8)O2A—C14A—H14D95.1
C13A—C10—S1A111.0 (8)C15A—C14A—H14D103.6
C9—C10—S1A119.9 (3)H14C—C14A—H14D103.7
C13—C10—S1110.6 (3)C14A—C15A—H15G110.4
C9—C10—S1121.65 (17)C14A—C15A—H15D108.7
C11—S1—C1091.9 (2)H15G—C15A—H15D109.5
C12—C11—S1112.1 (4)C14A—C15A—H15E109.4
C12—C11—H11124.0H15G—C15A—H15E109.5
S1—C11—H11123.9H15D—C15A—H15E109.5
C11—C12—C13110.6 (5)
C6—C1—C2—C30.2 (3)C13A—C10—S1—C1142 (5)
C1—C2—C3—N1−177.0 (2)C9—C10—S1—C11178.1 (3)
C1—C2—C3—C40.9 (3)S1A—C10—S1—C11−4.5 (4)
N1—C3—C4—C5176.8 (2)C10—S1—C11—C120.6 (3)
C2—C3—C4—C5−1.0 (3)S1—C11—C12—C13−0.7 (5)
C3—C4—C5—C60.0 (4)C13A—C10—C13—C12−7.3 (10)
C4—C5—C6—C11.0 (3)C9—C10—C13—C12−178.3 (4)
C4—C5—C6—C7179.4 (2)S1A—C10—C13—C12154 (4)
C2—C1—C6—C5−1.1 (3)S1—C10—C13—C12−0.2 (6)
C2—C1—C6—C7−179.63 (19)C11—C12—C13—C100.6 (7)
C5—C6—C7—O1176.5 (2)C13—C10—S1A—C11A−20 (4)
C1—C6—C7—O1−5.2 (3)C13A—C10—S1A—C11A−0.8 (17)
C5—C6—C7—C8−3.9 (3)C9—C10—S1A—C11A−175.2 (14)
C1—C6—C7—C8174.47 (19)S1—C10—S1A—C11A7.3 (14)
O1—C7—C8—C9−2.4 (3)C10—S1A—C11A—C12A0.0 (13)
C6—C7—C8—C9178.02 (19)S1A—C11A—C12A—C13A0.7 (16)
C7—C8—C9—C10−179.1 (2)C11A—C12A—C13A—C10−1(2)
C8—C9—C10—C13180.0 (4)C13—C10—C13A—C12A4(2)
C8—C9—C10—C13A11.2 (11)C9—C10—C13A—C12A175.1 (18)
C8—C9—C10—S1A−175.4 (4)S1A—C10—C13A—C12A1(2)
C8—C9—C10—S12.0 (3)S1—C10—C13A—C12A−136 (6)
C13—C10—S1—C11−0.2 (4)
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.162.931 (3)149
N1—H1B···Cg1ii0.862.803.597 (3)156
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1A⋯O1i0.862.162.931 (3)149
N1—H1B⋯Cg1ii0.862.803.597 (3)156

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the S1/C10–C13 ring.

  6 in total

Review 1.  Bioactivities of chalcones.

Authors:  J R Dimmock; D W Elias; M A Beazely; N M Kandepu
Journal:  Curr Med Chem       Date:  1999-12       Impact factor: 4.530

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

Review 3.  Chalcones: an update on cytotoxic and chemoprotective properties.

Authors:  M L Go; X Wu; X L Liu
Journal:  Curr Med Chem       Date:  2005       Impact factor: 4.530

4.  (E)-1-(2-Thien-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

Authors:  Thitipone Suwunwong; Suchada Chantrapromma; Paradorn Pakdeevanich; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-13

5.  (Z)-3-(9-Anthr-yl)-1-(2-thien-yl)prop-2-en-1-one.

Authors:  Hoong-Kun Fun; Thitipone Suwunwong; Nawong Boonnak; Suchada Chantrapromma
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-08-15

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  1 in total

1.  6-(4-Amino-phen-yl)-2-eth-oxy-4-(2-thien-yl)nicotinonitrile.

Authors:  Hoong-Kun Fun; Suchada Chantrapromma; Thawanrat Kobkeatthawin; Mahesh Padaki; Arun M Isloor
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-26
  1 in total

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