Literature DB >> 21578757

9,9-Dimethyl-12-phenyl-8,9-dihydro-12H-benzo[a]xanthen-11(10H)-one.

Yong Zhang1, Hong-Jun Zang, Bo-Wen Cheng.   

Abstract

The title compound, C(25)H(22)O(2), was synthesized via the three-component coupling of benzaldehyde, 2-naphthol and 5,5-dimethyl-cyclo-hexane-1,3-dione. In the crystal structure, centrosymmetrically related mol-ecules are linked into dimers by pairs of inter-molecular C-H⋯O hydrogen bonds. The dimers are further connected into a three-dimensional network by π-π aromatic stacking inter-actions involving the naphthalene ring system, with centroid-centroid separations of 3.695 (7) Å.

Entities:  

Year:  2009        PMID： 21578757      PMCID： PMC2971999          DOI： 10.1107/S1600536809046157

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


Related literature

For the biological and pharmacological activity of xanthenes and benzoxanthenes, see: Ion et al. (1998 ▶); Lambert et al. (1997 ▶); Poupelin et al. (1978 ▶); Saint-Ruf et al. (1975 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C25H22O2 M = 354.43 Triclinic, a = 9.1881 (18) Å b = 9.2317 (18) Å c = 12.866 (3) Å α = 72.78 (3)° β = 80.82 (3)° γ = 62.17 (2)° V = 921.6 (3) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 113 K 0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.984, T max = 0.989 8318 measured reflections 4294 independent reflections 2797 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.114 S = 0.97 4294 reflections 246 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.26 e Å−3 Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046157/rz2384sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046157/rz2384Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H22O2Z = 2
Mr = 354.43F(000) = 376
Triclinic, P1Dx = 1.277 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1881 (18) ÅCell parameters from 2907 reflections
b = 9.2317 (18) Åθ = 2.5–27.9°
c = 12.866 (3) ŵ = 0.08 mm−1
α = 72.78 (3)°T = 113 K
β = 80.82 (3)°Prism, colourless
γ = 62.17 (2)°0.20 × 0.18 × 0.14 mm
V = 921.6 (3) Å3
Rigaku Saturn CCD area-detector diffractometer4294 independent reflections
Radiation source: rotating anode2797 reflections with I > 2σ(I)
confocalRint = 0.027
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.5°
ω and φ scansh = −12→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −12→12
Tmin = 0.984, Tmax = 0.989l = −16→13
8318 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0691P)2] where P = (Fo2 + 2Fc2)/3
4294 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
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.
xyzUiso*/Ueq
O10.80464 (10)0.56824 (10)0.17827 (6)0.0210 (2)
O21.16069 (10)0.04959 (11)0.40301 (7)0.0304 (3)
C10.66568 (14)0.56096 (15)0.23792 (9)0.0183 (3)
C20.51931 (15)0.71327 (15)0.21330 (10)0.0233 (3)
H20.51950.80810.15820.028*
C30.37777 (14)0.72247 (16)0.26954 (10)0.0248 (3)
H30.27860.82420.25300.030*
C40.37678 (14)0.58228 (16)0.35227 (10)0.0210 (3)
C50.23201 (15)0.59156 (17)0.41469 (10)0.0258 (3)
H50.13280.69380.40030.031*
C60.23318 (15)0.45569 (18)0.49505 (10)0.0268 (3)
H60.13520.46390.53610.032*
C70.37922 (15)0.30371 (17)0.51717 (10)0.0240 (3)
H70.37920.20960.57310.029*
C80.52136 (14)0.28998 (16)0.45884 (9)0.0203 (3)
H80.61880.18620.47480.024*
C90.52538 (14)0.42815 (15)0.37510 (9)0.0175 (3)
C100.67273 (13)0.41870 (14)0.31377 (9)0.0165 (2)
C110.83294 (13)0.25608 (14)0.32854 (9)0.0165 (3)
H110.84520.19390.40730.020*
C120.97420 (13)0.30107 (15)0.29088 (9)0.0171 (3)
C131.13999 (14)0.17861 (16)0.33168 (9)0.0193 (3)
C141.28077 (15)0.22110 (17)0.28404 (10)0.0244 (3)
H14A1.38360.11440.28880.029*
H14B1.29380.28530.32840.029*
C151.25745 (14)0.32512 (16)0.16526 (9)0.0205 (3)
C161.09217 (14)0.48479 (15)0.15974 (10)0.0221 (3)
H16A1.10300.56200.19410.027*
H16B1.06460.54450.08250.027*
C170.95571 (14)0.44364 (15)0.21571 (9)0.0183 (3)
C180.83235 (13)0.14387 (14)0.26191 (9)0.0167 (3)
C190.82901 (15)−0.01023 (15)0.31132 (10)0.0225 (3)
H190.8283−0.04850.38850.027*
C200.82669 (16)−0.10895 (16)0.24890 (11)0.0283 (3)
H200.8240−0.21390.28380.034*
C210.82820 (15)−0.05570 (17)0.13675 (11)0.0263 (3)
H210.8265−0.12350.09440.032*
C220.83223 (15)0.09814 (16)0.08610 (10)0.0233 (3)
H220.83350.13580.00890.028*
C230.83433 (14)0.19590 (15)0.14836 (9)0.0197 (3)
H230.83720.30070.11320.024*
C241.25856 (16)0.21964 (16)0.09293 (10)0.0247 (3)
H24A1.23940.28810.01750.037*
H24B1.17140.18340.11790.037*
H24C1.36550.11980.09710.037*
C251.39520 (16)0.37858 (19)0.12682 (11)0.0319 (3)
H25A1.50170.27760.13410.048*
H25B1.39280.44950.17130.048*
H25C1.37960.44300.05040.048*
U11U22U33U12U13U23
O10.0171 (4)0.0158 (4)0.0237 (5)−0.0045 (3)−0.0001 (3)−0.0013 (3)
O20.0233 (5)0.0274 (5)0.0263 (5)−0.0047 (4)−0.0044 (4)0.0036 (4)
C10.0162 (6)0.0188 (6)0.0185 (6)−0.0062 (5)0.0009 (5)−0.0064 (5)
C20.0242 (6)0.0158 (6)0.0233 (7)−0.0037 (5)−0.0038 (5)−0.0030 (5)
C30.0182 (6)0.0192 (6)0.0289 (7)0.0009 (5)−0.0049 (5)−0.0085 (5)
C40.0170 (6)0.0229 (6)0.0214 (6)−0.0044 (5)−0.0020 (5)−0.0100 (5)
C50.0158 (6)0.0306 (7)0.0279 (7)−0.0033 (5)−0.0016 (5)−0.0143 (6)
C60.0182 (6)0.0419 (8)0.0238 (7)−0.0136 (6)0.0041 (5)−0.0150 (6)
C70.0244 (6)0.0313 (7)0.0197 (6)−0.0144 (6)0.0003 (5)−0.0081 (5)
C80.0186 (6)0.0233 (6)0.0190 (6)−0.0076 (5)−0.0012 (5)−0.0081 (5)
C90.0157 (5)0.0200 (6)0.0162 (6)−0.0051 (5)−0.0014 (4)−0.0079 (5)
C100.0159 (5)0.0159 (5)0.0167 (6)−0.0043 (5)−0.0021 (4)−0.0067 (5)
C110.0161 (5)0.0141 (5)0.0160 (6)−0.0040 (4)−0.0015 (4)−0.0033 (4)
C120.0151 (5)0.0180 (6)0.0171 (6)−0.0053 (5)−0.0008 (4)−0.0065 (5)
C130.0181 (6)0.0227 (6)0.0148 (6)−0.0058 (5)−0.0019 (5)−0.0064 (5)
C140.0181 (6)0.0323 (7)0.0221 (7)−0.0098 (5)−0.0034 (5)−0.0070 (5)
C150.0173 (6)0.0239 (6)0.0207 (7)−0.0090 (5)0.0001 (5)−0.0069 (5)
C160.0223 (6)0.0199 (6)0.0255 (7)−0.0108 (5)0.0012 (5)−0.0062 (5)
C170.0166 (6)0.0184 (6)0.0194 (6)−0.0057 (5)−0.0012 (4)−0.0073 (5)
C180.0123 (5)0.0163 (5)0.0195 (6)−0.0042 (4)0.0009 (4)−0.0060 (5)
C190.0248 (6)0.0190 (6)0.0205 (6)−0.0087 (5)0.0036 (5)−0.0044 (5)
C200.0333 (7)0.0208 (6)0.0329 (8)−0.0146 (6)0.0086 (6)−0.0105 (6)
C210.0259 (7)0.0263 (7)0.0317 (8)−0.0119 (5)0.0041 (5)−0.0164 (6)
C220.0226 (6)0.0264 (7)0.0208 (6)−0.0098 (5)0.0001 (5)−0.0081 (5)
C230.0196 (6)0.0181 (6)0.0207 (6)−0.0083 (5)0.0003 (5)−0.0044 (5)
C240.0261 (6)0.0259 (7)0.0205 (7)−0.0100 (5)0.0017 (5)−0.0079 (5)
C250.0240 (7)0.0409 (8)0.0344 (8)−0.0176 (6)0.0018 (6)−0.0104 (7)
O1—C171.3697 (15)C14—C151.5321 (17)
O1—C11.4002 (14)C14—H14A0.9900
O2—C131.2224 (15)C14—H14B0.9900
C1—C101.3651 (16)C15—C251.5262 (17)
C1—C21.4116 (17)C15—C241.5293 (18)
C2—C31.3620 (17)C15—C161.5382 (17)
C2—H20.9500C16—C171.4932 (17)
C3—C41.4144 (18)C16—H16A0.9900
C3—H30.9500C16—H16B0.9900
C4—C51.4195 (17)C18—C191.3886 (17)
C4—C91.4287 (17)C18—C231.3964 (17)
C5—C61.3659 (19)C19—C201.3902 (19)
C5—H50.9500C19—H190.9500
C6—C71.4062 (19)C20—C211.3800 (19)
C6—H60.9500C20—H200.9500
C7—C81.3689 (17)C21—C221.3916 (18)
C7—H70.9500C21—H210.9500
C8—C91.4167 (17)C22—C231.3805 (18)
C8—H80.9500C22—H220.9500
C9—C101.4328 (16)C23—H230.9500
C10—C111.5210 (16)C24—H24A0.9800
C11—C121.5084 (16)C24—H24B0.9800
C11—C181.5298 (17)C24—H24C0.9800
C11—H111.0000C25—H25A0.9800
C12—C171.3367 (16)C25—H25B0.9800
C12—C131.4730 (17)C25—H25C0.9800
C13—C141.5104 (17)
C17—O1—C1117.38 (9)C15—C14—H14B108.8
C10—C1—O1122.50 (10)H14A—C14—H14B107.7
C10—C1—C2123.34 (11)C25—C15—C24109.07 (11)
O1—C1—C2114.16 (10)C25—C15—C14110.56 (11)
C3—C2—C1119.12 (11)C24—C15—C14109.76 (11)
C3—C2—H2120.4C25—C15—C16108.86 (11)
C1—C2—H2120.4C24—C15—C16111.11 (10)
C2—C3—C4120.76 (11)C14—C15—C16107.46 (10)
C2—C3—H3119.6C17—C16—C15112.02 (10)
C4—C3—H3119.6C17—C16—H16A109.2
C3—C4—C5121.59 (11)C15—C16—H16A109.2
C3—C4—C9119.45 (11)C17—C16—H16B109.2
C5—C4—C9118.96 (11)C15—C16—H16B109.2
C6—C5—C4120.98 (12)H16A—C16—H16B107.9
C6—C5—H5119.5C12—C17—O1122.42 (11)
C4—C5—H5119.5C12—C17—C16125.56 (11)
C5—C6—C7120.07 (12)O1—C17—C16111.98 (10)
C5—C6—H6120.0C19—C18—C23118.23 (12)
C7—C6—H6120.0C19—C18—C11121.73 (10)
C8—C7—C6120.65 (12)C23—C18—C11120.04 (11)
C8—C7—H7119.7C18—C19—C20120.59 (12)
C6—C7—H7119.7C18—C19—H19119.7
C7—C8—C9121.00 (11)C20—C19—H19119.7
C7—C8—H8119.5C21—C20—C19120.56 (12)
C9—C8—H8119.5C21—C20—H20119.7
C8—C9—C4118.34 (11)C19—C20—H20119.7
C8—C9—C10122.35 (10)C20—C21—C22119.49 (13)
C4—C9—C10119.31 (11)C20—C21—H21120.3
C1—C10—C9117.94 (10)C22—C21—H21120.3
C1—C10—C11119.67 (10)C23—C22—C21119.78 (12)
C9—C10—C11122.36 (10)C23—C22—H22120.1
C12—C11—C10108.68 (9)C21—C22—H22120.1
C12—C11—C18109.88 (10)C22—C23—C18121.36 (11)
C10—C11—C18110.04 (10)C22—C23—H23119.3
C12—C11—H11109.4C18—C23—H23119.3
C10—C11—H11109.4C15—C24—H24A109.5
C18—C11—H11109.4C15—C24—H24B109.5
C17—C12—C13118.84 (11)H24A—C24—H24B109.5
C17—C12—C11121.87 (10)C15—C24—H24C109.5
C13—C12—C11119.12 (10)H24A—C24—H24C109.5
O2—C13—C12120.62 (11)H24B—C24—H24C109.5
O2—C13—C14121.87 (11)C15—C25—H25A109.5
C12—C13—C14117.49 (10)C15—C25—H25B109.5
C13—C14—C15113.72 (10)H25A—C25—H25B109.5
C13—C14—H14A108.8C15—C25—H25C109.5
C15—C14—H14A108.8H25A—C25—H25C109.5
C13—C14—H14B108.8H25B—C25—H25C109.5
C17—O1—C1—C10−15.68 (17)C18—C11—C12—C13−81.65 (13)
C17—O1—C1—C2163.81 (11)C17—C12—C13—O2177.56 (12)
C10—C1—C2—C32.0 (2)C11—C12—C13—O2−7.11 (18)
O1—C1—C2—C3−177.51 (11)C17—C12—C13—C14−0.99 (17)
C1—C2—C3—C40.5 (2)C11—C12—C13—C14174.34 (11)
C2—C3—C4—C5177.48 (13)O2—C13—C14—C15150.16 (12)
C2—C3—C4—C9−1.5 (2)C12—C13—C14—C15−31.31 (16)
C3—C4—C5—C6−179.36 (13)C13—C14—C15—C25174.07 (11)
C9—C4—C5—C6−0.4 (2)C13—C14—C15—C24−65.56 (14)
C4—C5—C6—C70.1 (2)C13—C14—C15—C1655.38 (14)
C5—C6—C7—C80.0 (2)C25—C15—C16—C17−169.02 (10)
C6—C7—C8—C90.19 (19)C24—C15—C16—C1770.84 (13)
C7—C8—C9—C4−0.50 (18)C14—C15—C16—C17−49.25 (14)
C7—C8—C9—C10178.98 (12)C13—C12—C17—O1−176.11 (11)
C3—C4—C9—C8179.59 (11)C11—C12—C17—O18.69 (19)
C5—C4—C9—C80.59 (18)C13—C12—C17—C166.36 (19)
C3—C4—C9—C100.09 (18)C11—C12—C17—C16−168.84 (11)
C5—C4—C9—C10−178.91 (12)C1—O1—C17—C1214.15 (18)
O1—C1—C10—C9176.12 (11)C1—O1—C17—C16−168.01 (10)
C2—C1—C10—C9−3.32 (19)C15—C16—C17—C1220.60 (18)
O1—C1—C10—C11−5.42 (18)C15—C16—C17—O1−157.15 (10)
C2—C1—C10—C11175.13 (11)C12—C11—C18—C19127.33 (11)
C8—C9—C10—C1−177.25 (11)C10—C11—C18—C19−113.03 (12)
C4—C9—C10—C12.23 (18)C12—C11—C18—C23−53.01 (13)
C8—C9—C10—C114.34 (18)C10—C11—C18—C2366.63 (13)
C4—C9—C10—C11−176.19 (11)C23—C18—C19—C20−0.39 (17)
C1—C10—C11—C1224.78 (15)C11—C18—C19—C20179.28 (11)
C9—C10—C11—C12−156.83 (11)C18—C19—C20—C210.21 (19)
C1—C10—C11—C18−95.58 (13)C19—C20—C21—C220.06 (18)
C9—C10—C11—C1882.81 (14)C20—C21—C22—C23−0.13 (18)
C10—C11—C12—C17−26.92 (16)C21—C22—C23—C18−0.05 (18)
C18—C11—C12—C1793.53 (13)C19—C18—C23—C220.31 (16)
C10—C11—C12—C13157.90 (11)C11—C18—C23—C22−179.36 (10)
D—H···AD—HH···AD···AD—H···A
C8—H8···O2i0.952.493.366 (2)154
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C8—H8⋯O2i 0.952.493.366 (2)154

Symmetry code: (i) .

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