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The title compound, C29H18O, crystallizes as dark-red plates. The mol­ecule shows a twisted and partial paddle-wheel conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016850/gk2001sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016850/gk2001Isup2.hkl
Contains datablock I

CCDC reference: 610770

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.090
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O1 .. 2.71 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SMART; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL97 and PLATON (Spek, 2003).

1,3-Diphenyl-2H-cyclopenta[l]phenanthren-2-one top
Crystal data top
C29H18OZ = 2
Mr = 382.43F(000) = 400
Triclinic, P1Dx = 1.350 Mg m3
a = 10.4562 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.5242 (3) ÅCell parameters from 9820 reflections
c = 10.5842 (3) Åθ = 2.3–42.7°
α = 60.960 (1)°µ = 0.08 mm1
β = 70.150 (1)°T = 93 K
γ = 89.446 (2)°Plate, dark red
V = 940.59 (5) Å30.32 × 0.26 × 0.13 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3224 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.5°, θmin = 2.1°
φ and ω scansh = 1212
28645 measured reflectionsk = 1212
3495 independent reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.331P]
where P = (Fo2 + 2Fc2)/3
3495 reflections(Δ/σ)max = 0.008
271 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.50681 (8)0.70890 (9)0.36152 (9)0.01946 (19)
C10.49816 (11)0.73745 (11)0.23909 (12)0.0152 (2)
C20.60055 (11)0.71943 (11)0.11078 (12)0.0150 (2)
C30.73203 (11)0.67212 (12)0.11719 (13)0.0157 (2)
C40.73778 (12)0.56138 (12)0.25819 (13)0.0189 (2)
H40.65610.51620.35070.023*
C50.86231 (13)0.51733 (13)0.26341 (14)0.0228 (3)
H50.86540.44230.35960.027*
C60.98225 (12)0.58213 (14)0.12922 (15)0.0246 (3)
H61.06680.54990.13310.029*
C70.97870 (12)0.69436 (13)0.01112 (14)0.0222 (3)
H71.06100.73990.10290.027*
C80.85478 (11)0.73954 (12)0.01672 (13)0.0181 (2)
H80.85300.81710.11240.022*
C90.54188 (11)0.75028 (11)0.00516 (12)0.0143 (2)
C100.57143 (11)0.71675 (11)0.12023 (12)0.0143 (2)
C110.66298 (11)0.62175 (12)0.13490 (12)0.0159 (2)
H110.71370.58590.06900.019*
C120.68049 (11)0.57955 (12)0.24399 (13)0.0170 (2)
H120.74370.51610.25330.020*
C130.60585 (11)0.62984 (12)0.33982 (13)0.0181 (2)
H130.61860.60200.41570.022*
C140.51250 (11)0.72090 (12)0.32438 (12)0.0174 (2)
H140.46010.75300.38860.021*
C150.49392 (10)0.76655 (11)0.21631 (12)0.0147 (2)
C160.39200 (10)0.86257 (11)0.19996 (12)0.0152 (2)
C170.33992 (11)0.94208 (12)0.31593 (13)0.0177 (2)
H170.37120.93560.40770.021*
C180.24348 (11)1.03029 (12)0.30007 (13)0.0188 (2)
H180.20971.08340.38070.023*
C190.19611 (11)1.04126 (12)0.16698 (13)0.0184 (2)
H190.12881.10020.15520.022*
C200.24794 (11)0.96555 (12)0.05155 (13)0.0171 (2)
H200.21660.97420.03890.021*
C210.34594 (11)0.87627 (11)0.06573 (12)0.0149 (2)
C220.41079 (11)0.80704 (11)0.04841 (12)0.0146 (2)
C230.37932 (11)0.79133 (12)0.19082 (12)0.0155 (2)
C240.25265 (11)0.80354 (12)0.29708 (12)0.0153 (2)
C250.12328 (11)0.73675 (12)0.32453 (13)0.0169 (2)
H250.11810.68840.27000.020*
C260.00273 (11)0.74011 (12)0.43005 (13)0.0183 (2)
H260.08430.69440.44730.022*
C270.00920 (12)0.81034 (13)0.51062 (13)0.0197 (2)
H270.07330.81270.58320.024*
C280.13656 (12)0.87688 (13)0.48467 (13)0.0204 (2)
H280.14090.92540.53930.024*
C290.25789 (11)0.87331 (12)0.37941 (13)0.0178 (2)
H290.34470.91840.36330.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0200 (4)0.0247 (4)0.0154 (4)0.0054 (3)0.0081 (3)0.0106 (3)
C10.0154 (5)0.0141 (5)0.0147 (5)0.0013 (4)0.0056 (4)0.0065 (4)
C20.0155 (5)0.0135 (5)0.0141 (5)0.0015 (4)0.0047 (4)0.0064 (4)
C30.0167 (5)0.0162 (5)0.0194 (5)0.0039 (4)0.0092 (4)0.0113 (4)
C40.0209 (6)0.0190 (5)0.0193 (6)0.0040 (4)0.0095 (4)0.0104 (5)
C50.0282 (6)0.0218 (6)0.0267 (6)0.0102 (5)0.0187 (5)0.0131 (5)
C60.0200 (6)0.0295 (6)0.0389 (7)0.0118 (5)0.0181 (5)0.0238 (6)
C70.0156 (5)0.0258 (6)0.0298 (6)0.0026 (4)0.0063 (5)0.0191 (5)
C80.0194 (5)0.0170 (5)0.0198 (5)0.0033 (4)0.0082 (4)0.0102 (5)
C90.0134 (5)0.0122 (5)0.0134 (5)0.0008 (4)0.0038 (4)0.0046 (4)
C100.0130 (5)0.0131 (5)0.0127 (5)0.0006 (4)0.0026 (4)0.0052 (4)
C110.0140 (5)0.0164 (5)0.0154 (5)0.0018 (4)0.0053 (4)0.0070 (4)
C120.0147 (5)0.0154 (5)0.0185 (5)0.0020 (4)0.0032 (4)0.0090 (4)
C130.0195 (5)0.0187 (5)0.0157 (5)0.0004 (4)0.0040 (4)0.0104 (5)
C140.0177 (5)0.0181 (5)0.0148 (5)0.0013 (4)0.0066 (4)0.0071 (4)
C150.0130 (5)0.0134 (5)0.0131 (5)0.0004 (4)0.0025 (4)0.0050 (4)
C160.0130 (5)0.0144 (5)0.0159 (5)0.0001 (4)0.0050 (4)0.0065 (4)
C170.0185 (5)0.0195 (5)0.0155 (5)0.0022 (4)0.0070 (4)0.0088 (5)
C180.0200 (5)0.0177 (5)0.0184 (5)0.0032 (4)0.0109 (4)0.0067 (5)
C190.0169 (5)0.0161 (5)0.0223 (6)0.0047 (4)0.0087 (4)0.0093 (5)
C200.0177 (5)0.0170 (5)0.0169 (5)0.0025 (4)0.0064 (4)0.0089 (4)
C210.0141 (5)0.0140 (5)0.0146 (5)0.0007 (4)0.0052 (4)0.0060 (4)
C220.0137 (5)0.0134 (5)0.0158 (5)0.0014 (4)0.0050 (4)0.0073 (4)
C230.0157 (5)0.0148 (5)0.0158 (5)0.0024 (4)0.0066 (4)0.0074 (4)
C240.0169 (5)0.0152 (5)0.0129 (5)0.0055 (4)0.0066 (4)0.0060 (4)
C250.0190 (5)0.0183 (5)0.0166 (5)0.0060 (4)0.0090 (4)0.0100 (4)
C260.0148 (5)0.0197 (5)0.0188 (5)0.0054 (4)0.0074 (4)0.0082 (5)
C270.0180 (5)0.0218 (6)0.0176 (5)0.0096 (4)0.0051 (4)0.0101 (5)
C280.0249 (6)0.0213 (6)0.0202 (6)0.0083 (5)0.0094 (5)0.0140 (5)
C290.0187 (5)0.0175 (5)0.0183 (5)0.0034 (4)0.0081 (4)0.0094 (5)
Geometric parameters (Å, º) top
O1—C11.2160 (13)C14—H140.9500
C1—C231.5043 (15)C15—C161.4868 (15)
C1—C21.5117 (14)C16—C171.3969 (15)
C2—C91.3568 (15)C16—C211.4156 (15)
C2—C31.4697 (15)C17—C181.3874 (16)
C3—C41.4000 (16)C17—H170.9500
C3—C81.4020 (16)C18—C191.3877 (16)
C4—C51.3877 (16)C18—H180.9500
C4—H40.9500C19—C201.3847 (15)
C5—C61.3862 (18)C19—H190.9500
C5—H50.9500C20—C211.4033 (15)
C6—C71.3915 (18)C20—H200.9500
C6—H60.9500C21—C221.4637 (15)
C7—C81.3861 (16)C22—C231.3528 (15)
C7—H70.9500C23—C241.4700 (15)
C8—H80.9500C24—C251.4005 (15)
C9—C101.4681 (15)C24—C291.3986 (15)
C9—C221.5062 (14)C25—C261.3852 (15)
C10—C111.4040 (15)C25—H250.9500
C10—C151.4142 (15)C26—C271.3893 (16)
C11—C121.3844 (15)C26—H260.9500
C11—H110.9500C27—C281.3864 (17)
C12—C131.3880 (16)C27—H270.9500
C12—H120.9500C28—C291.3899 (16)
C13—C141.3868 (16)C28—H280.9500
C13—H130.9500C29—H290.9500
C14—C151.3992 (15)
O1—C1—C23125.87 (10)C10—C15—C16120.58 (9)
O1—C1—C2126.80 (10)C17—C16—C21118.26 (10)
C23—C1—C2107.28 (9)C17—C16—C15121.33 (10)
C9—C2—C3131.79 (10)C21—C16—C15120.40 (9)
C9—C2—C1106.13 (9)C18—C17—C16121.45 (10)
C3—C2—C1122.06 (9)C18—C17—H17119.3
C4—C3—C8118.67 (10)C16—C17—H17119.3
C4—C3—C2120.60 (10)C19—C18—C17120.29 (10)
C8—C3—C2120.71 (10)C19—C18—H18119.9
C5—C4—C3120.29 (11)C17—C18—H18119.9
C5—C4—H4119.9C20—C19—C18119.37 (10)
C3—C4—H4119.9C20—C19—H19120.3
C4—C5—C6120.45 (11)C18—C19—H19120.3
C4—C5—H5119.8C19—C20—C21121.18 (10)
C6—C5—H5119.8C19—C20—H20119.4
C7—C6—C5119.92 (10)C21—C20—H20119.4
C7—C6—H6120.0C20—C21—C16119.43 (10)
C5—C6—H6120.0C20—C21—C22121.48 (10)
C8—C7—C6119.86 (11)C16—C21—C22118.88 (9)
C8—C7—H7120.1C23—C22—C21131.10 (10)
C6—C7—H7120.1C23—C22—C9109.80 (9)
C7—C8—C3120.78 (10)C21—C22—C9118.93 (9)
C7—C8—H8119.6C22—C23—C24131.27 (10)
C3—C8—H8119.6C22—C23—C1106.49 (9)
C2—C9—C10131.65 (10)C24—C23—C1121.89 (9)
C2—C9—C22109.68 (9)C25—C24—C29118.53 (10)
C10—C9—C22117.85 (9)C25—C24—C23119.78 (10)
C11—C10—C15119.01 (10)C29—C24—C23121.58 (10)
C11—C10—C9121.32 (9)C26—C25—C24121.01 (10)
C15—C10—C9119.22 (9)C26—C25—H25119.5
C12—C11—C10121.02 (10)C24—C25—H25119.5
C12—C11—H11119.5C25—C26—C27119.93 (10)
C10—C11—H11119.5C25—C26—H26120.0
C11—C12—C13120.06 (10)C27—C26—H26120.0
C11—C12—H12120.0C28—C27—C26119.69 (10)
C13—C12—H12120.0C28—C27—H27120.2
C14—C13—C12119.71 (10)C26—C27—H27120.2
C14—C13—H13120.1C27—C28—C29120.62 (10)
C12—C13—H13120.1C27—C28—H28119.7
C13—C14—C15121.40 (10)C29—C28—H28119.7
C13—C14—H14119.3C28—C29—C24120.22 (10)
C15—C14—H14119.3C28—C29—H29119.9
C14—C15—C10118.78 (10)C24—C29—H29119.9
C14—C15—C16120.63 (10)
O1—C1—C2—C9173.93 (10)C21—C16—C17—C181.25 (16)
C23—C1—C2—C93.62 (11)C15—C16—C17—C18179.17 (10)
O1—C1—C2—C34.23 (17)C16—C17—C18—C190.10 (17)
C23—C1—C2—C3178.21 (9)C17—C18—C19—C201.21 (16)
C9—C2—C3—C4137.46 (12)C18—C19—C20—C210.95 (16)
C1—C2—C3—C440.18 (15)C19—C20—C21—C160.41 (16)
C9—C2—C3—C844.20 (17)C19—C20—C21—C22174.21 (10)
C1—C2—C3—C8138.16 (10)C17—C16—C21—C201.49 (15)
C8—C3—C4—C51.58 (16)C15—C16—C21—C20178.93 (9)
C2—C3—C4—C5179.95 (10)C17—C16—C21—C22173.27 (9)
C3—C4—C5—C60.14 (17)C15—C16—C21—C226.31 (15)
C4—C5—C6—C71.41 (18)C20—C21—C22—C2312.17 (18)
C5—C6—C7—C80.91 (17)C16—C21—C22—C23173.19 (11)
C6—C7—C8—C30.84 (17)C20—C21—C22—C9162.59 (10)
C4—C3—C8—C72.08 (16)C16—C21—C22—C912.06 (14)
C2—C3—C8—C7179.56 (10)C2—C9—C22—C238.53 (12)
C3—C2—C9—C1015.79 (19)C10—C9—C22—C23162.32 (9)
C1—C2—C9—C10162.12 (10)C2—C9—C22—C21167.27 (9)
C3—C2—C9—C22175.06 (11)C10—C9—C22—C2121.88 (14)
C1—C2—C9—C227.03 (11)C21—C22—C23—C2417.4 (2)
C2—C9—C10—C119.14 (17)C9—C22—C23—C24167.43 (11)
C22—C9—C10—C11159.30 (9)C21—C22—C23—C1169.38 (11)
C2—C9—C10—C15178.57 (11)C9—C22—C23—C15.74 (11)
C22—C9—C10—C1513.00 (14)O1—C1—C23—C22179.14 (10)
C15—C10—C11—C121.55 (15)C2—C1—C23—C221.56 (11)
C9—C10—C11—C12173.86 (9)O1—C1—C23—C245.18 (17)
C10—C11—C12—C130.73 (16)C2—C1—C23—C24172.41 (9)
C11—C12—C13—C140.82 (16)C22—C23—C24—C2544.63 (17)
C12—C13—C14—C151.54 (16)C1—C23—C24—C25127.65 (11)
C13—C14—C15—C100.70 (16)C22—C23—C24—C29139.14 (12)
C13—C14—C15—C16179.19 (10)C1—C23—C24—C2948.58 (15)
C11—C10—C15—C140.83 (15)C29—C24—C25—C260.38 (16)
C9—C10—C15—C14173.30 (9)C23—C24—C25—C26176.73 (10)
C11—C10—C15—C16177.66 (9)C24—C25—C26—C270.10 (16)
C9—C10—C15—C165.18 (14)C25—C26—C27—C280.07 (16)
C14—C15—C16—C1717.49 (15)C26—C27—C28—C290.34 (17)
C10—C15—C16—C17164.05 (10)C27—C28—C29—C240.63 (17)
C14—C15—C16—C21162.94 (10)C25—C24—C29—C280.64 (16)
C10—C15—C16—C2115.52 (15)C23—C24—C29—C28176.92 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.952.713.5874 (14)154
Symmetry code: (i) x+1, y+1, z+1.
 

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