Literature DB >> 23125703

(E)-1-(3-Hy-droxy-phen-yl)-3-[4-(tetra-dec-yl-oxy)phen-yl]prop-2-en-1-one.

Siti Muhaini Haris Fadzillah1, Zainab Ngaini, Hasnain Hussain, Ibrahim Abdul Razak, Safra Izuani Jama Asik.   

Abstract

In the title compound, C(29)H(40)O(3), the enone moiety adopts an s-cis conformation. The dihedral angle between the benzene rings is 4.33 (5)° The least-squares mean line through the tetra-decyl side chain forms a dihedral angle of 83.99 (7)° with the normal to the attached benzene ring. In the crystal, O-H⋯O and C-H⋯O hydrogen bonds involving the keto and the hy-droxy O atoms form ribbons along [-41-1]. The crystal structure also features C-H⋯π inter-actions.

Entities:  

Year:  2012        PMID： 23125703      PMCID： PMC3470259          DOI： 10.1107/S1600536812038020

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


Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Won et al. (2005 ▶); Zhao et al. (2005 ▶); Satyanarayana et al. (2004 ▶). For related structures, see: Razak et al. (2009 ▶); Ngaini et al. (2010 ▶, 2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C29H40O3 M = 436.61 Triclinic, a = 6.5138 (16) Å b = 10.155 (2) Å c = 19.264 (5) Å α = 75.361 (6)° β = 85.872 (7)° γ = 83.013 (6)° V = 1222.6 (5) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 100 K 0.29 × 0.12 × 0.08 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.979, T max = 0.994 26295 measured reflections 7155 independent reflections 5052 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.147 S = 0.95 7155 reflections 293 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.40 e Å−3 Δρmin = −0.23 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT (Bruker, 2009 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038020/rz5001sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038020/rz5001Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812038020/rz5001Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C29H40O3Z = 2
Mr = 436.61F(000) = 476
Triclinic, P1Dx = 1.186 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5138 (16) ÅCell parameters from 5533 reflections
b = 10.155 (2) Åθ = 2.6–30.1°
c = 19.264 (5) ŵ = 0.08 mm−1
α = 75.361 (6)°T = 100 K
β = 85.872 (7)°Block, colourless
γ = 83.013 (6)°0.29 × 0.12 × 0.08 mm
V = 1222.6 (5) Å3
Bruker APEX DUO CCD area-detector diffractometer7155 independent reflections
Radiation source: fine-focus sealed tube5052 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 30.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −9→9
Tmin = 0.979, Tmax = 0.994k = −14→14
26295 measured reflectionsl = −27→27
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 0.95w = 1/[σ2(Fo2) + (0.0913P)2 + 0.1348P] where P = (Fo2 + 2Fc2)/3
7155 reflections(Δ/σ)max < 0.001
293 parametersΔρmax = 0.40 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (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 > 2sigma(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*/Ueq
O11.67428 (14)0.11123 (9)0.62770 (5)0.0245 (2)
O21.18019 (13)0.07397 (8)0.44966 (4)0.01891 (19)
O30.03940 (13)0.44359 (8)0.27772 (4)0.01874 (19)
C11.10873 (19)0.31949 (12)0.55966 (6)0.0187 (2)
H1A0.98150.36690.54520.022*
C21.2188 (2)0.35854 (12)0.60903 (6)0.0210 (3)
H2A1.16480.43260.62730.025*
C31.4073 (2)0.28868 (12)0.63122 (6)0.0193 (2)
H3A1.47980.31580.66420.023*
C41.48910 (19)0.17725 (11)0.60411 (6)0.0168 (2)
C51.37933 (18)0.13808 (11)0.55490 (6)0.0159 (2)
H5A1.43310.06350.53700.019*
C61.19002 (18)0.20879 (11)0.53191 (5)0.0147 (2)
C71.08792 (18)0.16453 (11)0.47562 (5)0.0149 (2)
C80.88422 (19)0.23100 (11)0.45154 (6)0.0175 (2)
H8A0.81780.29850.47260.021*
C90.79155 (18)0.19653 (11)0.39981 (6)0.0157 (2)
H9A0.86090.12630.38140.019*
C100.59375 (18)0.25740 (11)0.36941 (5)0.0148 (2)
C110.51656 (19)0.20878 (11)0.31596 (6)0.0165 (2)
H11A0.59110.13530.30170.020*
C120.33214 (19)0.26639 (11)0.28337 (6)0.0162 (2)
H12A0.28380.23180.24800.019*
C130.22125 (18)0.37651 (11)0.30454 (5)0.0151 (2)
C140.29544 (19)0.42667 (11)0.35819 (6)0.0167 (2)
H14A0.22110.50050.37220.020*
C150.47706 (18)0.36780 (11)0.39023 (6)0.0163 (2)
H15A0.52350.40150.42620.020*
C16−0.04781 (19)0.40731 (11)0.21970 (6)0.0169 (2)
H16A−0.07840.31280.23360.020*
H16B0.04670.41940.17790.020*
C17−0.24440 (19)0.50374 (11)0.20419 (6)0.0166 (2)
H17A−0.21120.59670.19810.020*
H17B−0.33980.48360.24560.020*
C18−0.35328 (18)0.49674 (11)0.13800 (6)0.0166 (2)
H18A−0.38930.40460.14360.020*
H18B−0.26050.51820.09600.020*
C19−0.54867 (18)0.59744 (11)0.12739 (6)0.0167 (2)
H19A−0.64270.57180.16870.020*
H19B−0.51170.68780.12590.020*
C20−0.66224 (19)0.60539 (11)0.05978 (6)0.0171 (2)
H20A−0.56960.63180.01810.021*
H20B−0.70090.51550.06100.021*
C21−0.85585 (18)0.70750 (11)0.05220 (6)0.0169 (2)
H21A−0.81680.79650.05250.020*
H21B−0.94890.67960.09360.020*
C22−0.97131 (19)0.72124 (11)−0.01577 (6)0.0169 (2)
H22A−0.87970.7513−0.05730.020*
H22B−1.00860.6321−0.01670.020*
C23−1.16618 (18)0.82165 (11)−0.02125 (6)0.0174 (2)
H23A−1.25820.79070.02000.021*
H23B−1.12880.9103−0.01950.021*
C24−1.28162 (19)0.83808 (11)−0.08925 (6)0.0175 (2)
H24A−1.31870.7494−0.09120.021*
H24B−1.19010.8696−0.13060.021*
C25−1.47682 (19)0.93813 (11)−0.09405 (6)0.0178 (2)
H25A−1.43951.0267−0.09210.021*
H25B−1.56810.9066−0.05260.021*
C26−1.59373 (19)0.95536 (11)−0.16197 (6)0.0173 (2)
H26A−1.50280.9869−0.20350.021*
H26B−1.63190.8670−0.16390.021*
C27−1.78807 (19)1.05606 (12)−0.16597 (6)0.0189 (2)
H27A−1.74841.1453−0.16650.023*
H27B−1.87451.0272−0.12290.023*
C28−1.9153 (2)1.06977 (12)−0.23116 (6)0.0193 (2)
H28A−1.82861.0958−0.27440.023*
H28B−1.96110.9817−0.22980.023*
C29−2.1028 (2)1.17540 (13)−0.23412 (7)0.0252 (3)
H29A−2.17811.1808−0.27600.038*
H29B−2.05811.2631−0.23640.038*
H29C−2.19071.1490−0.19190.038*
H1O11.718 (3)0.046 (2)0.6024 (10)0.056 (5)*
U11U22U33U12U13U23
O10.0180 (5)0.0297 (5)0.0300 (4)0.0089 (4)−0.0123 (4)−0.0174 (4)
O20.0174 (5)0.0197 (4)0.0206 (4)0.0027 (3)−0.0034 (3)−0.0084 (3)
O30.0155 (4)0.0225 (4)0.0195 (4)0.0050 (3)−0.0090 (3)−0.0086 (3)
C10.0145 (6)0.0203 (5)0.0213 (5)0.0036 (4)−0.0041 (4)−0.0069 (4)
C20.0192 (6)0.0203 (5)0.0260 (5)0.0029 (5)−0.0033 (5)−0.0120 (4)
C30.0175 (6)0.0214 (5)0.0217 (5)−0.0006 (5)−0.0051 (4)−0.0100 (4)
C40.0136 (6)0.0188 (5)0.0180 (5)0.0007 (4)−0.0030 (4)−0.0050 (4)
C50.0150 (6)0.0164 (5)0.0170 (5)0.0010 (4)−0.0030 (4)−0.0059 (4)
C60.0137 (6)0.0160 (5)0.0144 (4)−0.0008 (4)−0.0018 (4)−0.0035 (4)
C70.0145 (6)0.0150 (5)0.0145 (4)−0.0007 (4)−0.0021 (4)−0.0026 (4)
C80.0149 (6)0.0190 (5)0.0185 (5)0.0021 (4)−0.0031 (4)−0.0058 (4)
C90.0143 (6)0.0150 (5)0.0167 (5)0.0005 (4)−0.0022 (4)−0.0026 (4)
C100.0126 (6)0.0160 (5)0.0148 (4)−0.0005 (4)−0.0020 (4)−0.0019 (4)
C110.0157 (6)0.0171 (5)0.0171 (5)0.0008 (4)−0.0016 (4)−0.0059 (4)
C120.0149 (6)0.0186 (5)0.0157 (4)0.0001 (4)−0.0036 (4)−0.0056 (4)
C130.0122 (5)0.0168 (5)0.0154 (4)0.0013 (4)−0.0034 (4)−0.0027 (4)
C140.0148 (6)0.0177 (5)0.0183 (5)0.0018 (4)−0.0025 (4)−0.0070 (4)
C150.0151 (6)0.0184 (5)0.0159 (5)−0.0004 (4)−0.0037 (4)−0.0052 (4)
C160.0159 (6)0.0189 (5)0.0165 (5)0.0008 (4)−0.0058 (4)−0.0051 (4)
C170.0140 (6)0.0179 (5)0.0172 (5)0.0016 (4)−0.0042 (4)−0.0037 (4)
C180.0140 (6)0.0177 (5)0.0179 (5)0.0018 (4)−0.0052 (4)−0.0043 (4)
C190.0139 (6)0.0182 (5)0.0173 (5)0.0019 (4)−0.0037 (4)−0.0042 (4)
C200.0150 (6)0.0185 (5)0.0178 (5)0.0023 (4)−0.0043 (4)−0.0051 (4)
C210.0147 (6)0.0189 (5)0.0167 (5)0.0018 (4)−0.0041 (4)−0.0046 (4)
C220.0154 (6)0.0182 (5)0.0171 (5)0.0013 (4)−0.0048 (4)−0.0046 (4)
C230.0154 (6)0.0198 (5)0.0166 (5)0.0025 (4)−0.0049 (4)−0.0047 (4)
C240.0166 (6)0.0180 (5)0.0175 (5)0.0022 (4)−0.0050 (4)−0.0043 (4)
C250.0166 (6)0.0184 (5)0.0181 (5)0.0030 (4)−0.0056 (4)−0.0050 (4)
C260.0170 (6)0.0174 (5)0.0175 (5)0.0018 (4)−0.0056 (4)−0.0044 (4)
C270.0190 (6)0.0181 (5)0.0202 (5)0.0030 (5)−0.0077 (4)−0.0064 (4)
C280.0189 (6)0.0216 (5)0.0177 (5)0.0021 (5)−0.0063 (4)−0.0058 (4)
C290.0220 (7)0.0282 (6)0.0269 (6)0.0062 (5)−0.0112 (5)−0.0107 (5)
O1—C41.3561 (14)C18—C191.5239 (15)
O1—H1O10.927 (19)C18—H18A0.9700
O2—C71.2296 (13)C18—H18B0.9700
O3—C131.3594 (13)C19—C201.5237 (15)
O3—C161.4346 (13)C19—H19A0.9700
C1—C21.3906 (16)C19—H19B0.9700
C1—C61.3958 (14)C20—C211.5228 (15)
C1—H1A0.9300C20—H20A0.9700
C2—C31.3799 (17)C20—H20B0.9700
C2—H2A0.9300C21—C221.5244 (15)
C3—C41.3959 (15)C21—H21A0.9700
C3—H3A0.9300C21—H21B0.9700
C4—C51.3876 (15)C22—C231.5205 (16)
C5—C61.3910 (16)C22—H22A0.9700
C5—H5A0.9300C22—H22B0.9700
C6—C71.4977 (15)C23—C241.5199 (15)
C7—C81.4642 (16)C23—H23A0.9700
C8—C91.3394 (15)C23—H23B0.9700
C8—H8A0.9300C24—C251.5208 (16)
C9—C101.4550 (16)C24—H24A0.9700
C9—H9A0.9300C24—H24B0.9700
C10—C111.3960 (14)C25—C261.5224 (15)
C10—C151.4041 (15)C25—H25A0.9700
C11—C121.3898 (16)C25—H25B0.9700
C11—H11A0.9300C26—C271.5210 (16)
C12—C131.3892 (14)C26—H26A0.9700
C12—H12A0.9300C26—H26B0.9700
C13—C141.3996 (14)C27—C281.5220 (15)
C14—C151.3728 (15)C27—H27A0.9700
C14—H14A0.9300C27—H27B0.9700
C15—H15A0.9300C28—C291.5186 (17)
C16—C171.5133 (15)C28—H28A0.9700
C16—H16A0.9700C28—H28B0.9700
C16—H16B0.9700C29—H29A0.9600
C17—C181.5238 (15)C29—H29B0.9600
C17—H17A0.9700C29—H29C0.9600
C17—H17B0.9700
C4—O1—H1O1109.7 (12)C20—C19—H19A108.6
C13—O3—C16120.08 (8)C18—C19—H19A108.6
C2—C1—C6119.72 (11)C20—C19—H19B108.6
C2—C1—H1A120.1C18—C19—H19B108.6
C6—C1—H1A120.1H19A—C19—H19B107.5
C3—C2—C1120.77 (10)C21—C20—C19112.36 (9)
C3—C2—H2A119.6C21—C20—H20A109.1
C1—C2—H2A119.6C19—C20—H20A109.1
C2—C3—C4119.90 (10)C21—C20—H20B109.1
C2—C3—H3A120.1C19—C20—H20B109.1
C4—C3—H3A120.1H20A—C20—H20B107.9
O1—C4—C5122.73 (9)C20—C21—C22114.06 (9)
O1—C4—C3117.87 (10)C20—C21—H21A108.7
C5—C4—C3119.40 (10)C22—C21—H21A108.7
C4—C5—C6120.95 (10)C20—C21—H21B108.7
C4—C5—H5A119.5C22—C21—H21B108.7
C6—C5—H5A119.5H21A—C21—H21B107.6
C5—C6—C1119.26 (10)C23—C22—C21112.97 (9)
C5—C6—C7117.38 (9)C23—C22—H22A109.0
C1—C6—C7123.31 (10)C21—C22—H22A109.0
O2—C7—C8121.41 (10)C23—C22—H22B109.0
O2—C7—C6118.66 (10)C21—C22—H22B109.0
C8—C7—C6119.91 (9)H22A—C22—H22B107.8
C9—C8—C7121.35 (10)C24—C23—C22113.65 (9)
C9—C8—H8A119.3C24—C23—H23A108.8
C7—C8—H8A119.3C22—C23—H23A108.8
C8—C9—C10126.83 (10)C24—C23—H23B108.8
C8—C9—H9A116.6C22—C23—H23B108.8
C10—C9—H9A116.6H23A—C23—H23B107.7
C11—C10—C15117.57 (10)C23—C24—C25113.25 (9)
C11—C10—C9119.95 (10)C23—C24—H24A108.9
C15—C10—C9122.45 (10)C25—C24—H24A108.9
C12—C11—C10122.27 (10)C23—C24—H24B108.9
C12—C11—H11A118.9C25—C24—H24B108.9
C10—C11—H11A118.9H24A—C24—H24B107.7
C13—C12—C11118.83 (10)C24—C25—C26113.70 (9)
C13—C12—H12A120.6C24—C25—H25A108.8
C11—C12—H12A120.6C26—C25—H25A108.8
O3—C13—C12125.69 (10)C24—C25—H25B108.8
O3—C13—C14114.44 (9)C26—C25—H25B108.8
C12—C13—C14119.86 (10)H25A—C25—H25B107.7
C15—C14—C13120.53 (10)C27—C26—C25112.98 (9)
C15—C14—H14A119.7C27—C26—H26A109.0
C13—C14—H14A119.7C25—C26—H26A109.0
C14—C15—C10120.92 (10)C27—C26—H26B109.0
C14—C15—H15A119.5C25—C26—H26B109.0
C10—C15—H15A119.5H26A—C26—H26B107.8
O3—C16—C17104.86 (8)C26—C27—C28114.37 (9)
O3—C16—H16A110.8C26—C27—H27A108.7
C17—C16—H16A110.8C28—C27—H27A108.7
O3—C16—H16B110.8C26—C27—H27B108.7
C17—C16—H16B110.8C28—C27—H27B108.7
H16A—C16—H16B108.9H27A—C27—H27B107.6
C16—C17—C18114.84 (9)C29—C28—C27112.26 (9)
C16—C17—H17A108.6C29—C28—H28A109.2
C18—C17—H17A108.6C27—C28—H28A109.2
C16—C17—H17B108.6C29—C28—H28B109.2
C18—C17—H17B108.6C27—C28—H28B109.2
H17A—C17—H17B107.5H28A—C28—H28B107.9
C17—C18—C19110.54 (9)C28—C29—H29A109.5
C17—C18—H18A109.5C28—C29—H29B109.5
C19—C18—H18A109.5H29A—C29—H29B109.5
C17—C18—H18B109.5C28—C29—H29C109.5
C19—C18—H18B109.5H29A—C29—H29C109.5
H18A—C18—H18B108.1H29B—C29—H29C109.5
C20—C19—C18114.83 (9)
C6—C1—C2—C3−0.31 (19)C16—O3—C13—C12−3.73 (17)
C1—C2—C3—C4−0.14 (19)C16—O3—C13—C14176.57 (10)
C2—C3—C4—O1−179.67 (11)C11—C12—C13—O3179.88 (11)
C2—C3—C4—C50.08 (18)C11—C12—C13—C14−0.44 (17)
O1—C4—C5—C6−179.82 (11)O3—C13—C14—C15179.62 (10)
C3—C4—C5—C60.43 (18)C12—C13—C14—C15−0.09 (18)
C4—C5—C6—C1−0.88 (18)C13—C14—C15—C100.82 (18)
C4—C5—C6—C7176.62 (10)C11—C10—C15—C14−0.98 (17)
C2—C1—C6—C50.81 (18)C9—C10—C15—C14177.11 (11)
C2—C1—C6—C7−176.53 (11)C13—O3—C16—C17−179.19 (9)
C5—C6—C7—O2−3.99 (16)O3—C16—C17—C18173.04 (9)
C1—C6—C7—O2173.39 (11)C16—C17—C18—C19179.95 (10)
C5—C6—C7—C8177.31 (10)C17—C18—C19—C20176.22 (10)
C1—C6—C7—C8−5.30 (17)C18—C19—C20—C21179.98 (10)
O2—C7—C8—C9−0.64 (18)C19—C20—C21—C22178.56 (10)
C6—C7—C8—C9178.02 (11)C20—C21—C22—C23178.85 (10)
C7—C8—C9—C10−177.78 (11)C21—C22—C23—C24179.19 (10)
C8—C9—C10—C11−179.31 (12)C22—C23—C24—C25179.71 (10)
C8—C9—C10—C152.64 (19)C23—C24—C25—C26−179.99 (10)
C15—C10—C11—C120.44 (17)C24—C25—C26—C27−179.83 (10)
C9—C10—C11—C12−177.70 (11)C25—C26—C27—C28−176.74 (10)
C10—C11—C12—C130.25 (18)C26—C27—C28—C29−177.78 (11)
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O2i0.93 (2)1.80 (2)2.7269 (14)175.6 (18)
C29—H29A···O1ii0.962.443.3589 (18)160
C17—H17B···Cg1iii0.972.733.6159 (16)152
C28—H28A···Cg2iv0.972.933.8481 (16)159
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C10–C15 and C1–C6 rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1—H1O1⋯O2i 0.93 (2)1.80 (2)2.7269 (14)175.6 (18)
C29—H29A⋯O1ii 0.962.443.3589 (18)160
C17—H17B⋯Cg1iii 0.972.733.6159 (16)152
C28—H28A⋯Cg2iv 0.972.933.8481 (16)159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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