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The title compound, C29H24O2, has mirror symmetry with the cyclo­propane C atoms lying on the mirror plane. The fluorene system is essentially planar and makes dihedral angles of 91.43 (4) and 23.50 (6)° with the cyclo­propane and substituted benzene rings, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005150/xu6115sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005150/xu6115Isup2.hkl
Contains datablock I

CCDC reference: 601278

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.119
  • Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT413_ALERT_2_C Short Inter XH3 .. XHn H16C .. H16C .. 2.10 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 1322 Count of symmetry unique reflns 1330 Completeness (_total/calc) 99.40% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.

2',7'-Bis(4-methoxyphenyl)-spiro[cyclopropane-1,9'-9H-fluorene] top
Crystal data top
C29H24O2F(000) = 856
Mr = 404.48Dx = 1.272 Mg m3
Orthorhombic, Cmc21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2Cell parameters from 8306 reflections
a = 23.307 (12) Åθ = 3.2–27.5°
b = 9.841 (4) ŵ = 0.08 mm1
c = 9.211 (4) ÅT = 295 K
V = 2112.7 (17) Å3Block, yellow
Z = 40.32 × 0.28 × 0.12 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1077 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 27.5°, θmin = 3.2°
Detector resolution: 10 pixels mm-1h = 3030
ω scansk = 1212
10172 measured reflectionsl = 1111
1322 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.078P)2 + 0.1214P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1322 reflectionsΔρmax = 0.15 e Å3
147 parametersΔρmin = 0.15 e Å3
1 restraintExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0040 (11)
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
C10.55077 (9)0.67722 (19)0.6665 (3)0.0524 (5)
C20.53114 (9)0.5595 (2)0.5957 (3)0.0554 (5)
C30.56987 (10)0.4659 (2)0.5417 (4)0.0688 (7)
H30.55700.38830.49410.083*
C40.62763 (10)0.4888 (3)0.5592 (4)0.0691 (7)
H40.65360.42550.52280.083*
C50.64858 (9)0.6042 (2)0.6300 (3)0.0558 (6)
C60.60911 (9)0.6999 (2)0.6840 (3)0.0552 (6)
H60.62200.77770.73100.066*
C70.50000.8529 (3)0.8415 (5)0.0649 (9)
H7A0.53510.85910.89780.078*
C80.50000.9136 (3)0.6932 (5)0.0638 (9)
H8A0.53510.95640.65980.077*
C90.50000.7605 (3)0.7103 (4)0.0531 (7)
C100.71157 (9)0.6218 (2)0.6478 (3)0.0565 (5)
C110.75014 (11)0.5563 (3)0.5550 (3)0.0719 (7)
H110.73590.50380.47910.086*
C120.80867 (11)0.5673 (3)0.5727 (3)0.0732 (7)
H120.83320.52280.50890.088*
C130.83092 (9)0.6433 (2)0.6838 (3)0.0621 (6)
C140.79434 (11)0.7112 (3)0.7760 (3)0.0681 (7)
H140.80900.76370.85130.082*
C150.73523 (11)0.7007 (3)0.7560 (3)0.0655 (7)
H150.71090.74850.81770.079*
C160.91413 (12)0.7108 (4)0.8147 (5)0.0974 (11)
H16A0.89920.67090.90190.146*
H16B0.90500.80590.81270.146*
H16C0.95500.69950.81210.146*
O10.88949 (7)0.6464 (2)0.6930 (3)0.0846 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0469 (11)0.0521 (9)0.0584 (12)0.0035 (8)0.0010 (10)0.0007 (11)
C20.0482 (12)0.0544 (11)0.0637 (13)0.0017 (8)0.0010 (10)0.0006 (11)
C30.0609 (13)0.0563 (11)0.0894 (19)0.0025 (10)0.0007 (14)0.0155 (12)
C40.0557 (12)0.0629 (12)0.0888 (19)0.0113 (11)0.0020 (13)0.0117 (14)
C50.0470 (11)0.0577 (11)0.0628 (13)0.0072 (9)0.0009 (10)0.0007 (10)
C60.0482 (11)0.0558 (11)0.0616 (14)0.0036 (9)0.0017 (10)0.0051 (11)
C70.0500 (18)0.0667 (18)0.078 (2)0.0000.0000.0179 (18)
C80.0486 (17)0.0523 (15)0.091 (3)0.0000.0000.0004 (18)
C90.0432 (15)0.0534 (14)0.0626 (17)0.0000.0000.0045 (15)
C100.0475 (11)0.0585 (11)0.0636 (13)0.0085 (9)0.0004 (10)0.0031 (10)
C110.0551 (13)0.0804 (15)0.0802 (18)0.0114 (11)0.0049 (12)0.0177 (15)
C120.0540 (13)0.0831 (15)0.0826 (18)0.0169 (11)0.0015 (13)0.0151 (16)
C130.0445 (11)0.0685 (12)0.0731 (16)0.0089 (9)0.0008 (11)0.0028 (13)
C140.0513 (13)0.0825 (16)0.0705 (14)0.0028 (12)0.0021 (11)0.0119 (13)
C150.0485 (13)0.0774 (15)0.0707 (16)0.0080 (11)0.0057 (11)0.0078 (13)
C160.0515 (15)0.131 (3)0.110 (3)0.0041 (15)0.0146 (18)0.029 (2)
O10.0425 (9)0.1087 (13)0.1026 (15)0.0130 (8)0.0053 (10)0.0250 (14)
Geometric parameters (Å, º) top
C1—C61.387 (3)C9—C1i1.495 (3)
C1—C21.406 (3)C10—C151.379 (4)
C1—C91.495 (3)C10—C111.398 (4)
C2—C31.382 (3)C11—C121.378 (4)
C2—C2i1.452 (4)C11—H110.9300
C3—C41.374 (3)C12—C131.369 (4)
C3—H30.9300C12—H120.9300
C4—C51.398 (4)C13—O11.368 (3)
C4—H40.9300C13—C141.377 (4)
C5—C61.407 (3)C14—C151.394 (3)
C5—C101.487 (3)C14—H140.9300
C6—H60.9300C15—H150.9300
C7—C81.490 (6)C16—O11.409 (5)
C7—C91.512 (5)C16—H16A0.9600
C7—H7A0.9700C16—H16B0.9600
C8—C91.515 (4)C16—H16C0.9600
C8—H8A0.9700
C6—C1—C2120.34 (19)C1—C9—C8121.14 (17)
C6—C1—C9131.0 (2)C7—C9—C859.0 (2)
C2—C1—C9108.62 (19)C15—C10—C11116.4 (2)
C3—C2—C1120.2 (2)C15—C10—C5122.7 (2)
C3—C2—C2i130.77 (14)C11—C10—C5120.9 (2)
C1—C2—C2i108.99 (12)C12—C11—C10121.8 (3)
C4—C3—C2119.2 (2)C12—C11—H11119.1
C4—C3—H3120.4C10—C11—H11119.1
C2—C3—H3120.4C13—C12—C11120.4 (2)
C3—C4—C5122.0 (2)C13—C12—H12119.8
C3—C4—H4119.0C11—C12—H12119.8
C5—C4—H4119.0O1—C13—C12115.9 (2)
C4—C5—C6118.7 (2)O1—C13—C14124.7 (2)
C4—C5—C10119.38 (19)C12—C13—C14119.4 (2)
C6—C5—C10121.9 (2)C13—C14—C15119.6 (3)
C1—C6—C5119.5 (2)C13—C14—H14120.2
C1—C6—H6120.2C15—C14—H14120.2
C5—C6—H6120.2C10—C15—C14122.2 (2)
C8—C7—C960.6 (2)C10—C15—H15118.9
C8—C7—H7A117.7C14—C15—H15118.9
C9—C7—H7A117.7O1—C16—H16A109.5
C7—C8—C960.4 (2)O1—C16—H16B109.5
C7—C8—H8A117.7H16A—C16—H16B109.5
C9—C8—H8A117.7O1—C16—H16C109.5
C1i—C9—C1104.7 (3)H16A—C16—H16C109.5
C1i—C9—C7123.04 (17)H16B—C16—H16C109.5
C1—C9—C7123.04 (17)C13—O1—C16117.8 (2)
C1i—C9—C8121.14 (17)
Symmetry code: (i) x+1, y, z.
 

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