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In the title compound [systematic name: 9-(1,3-diphenylprop-2-ynylidene)fluorene], C28H18, the two halves of the fluorene moiety subtend an angle of 7.84 (9)°; the interplanar angle about the exocyclic double bond is 12.3 (1)°. The packing involves three C—H...π contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003976/bt6414sup1.cif
Contains datablocks 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003976/bt64143sup2.hkl
Contains datablock 3

CCDC reference: 236108

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.076
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C11 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C12 - C13 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP5 (Siemens, 1994); software used to prepare material for publication: SHELXL97.

10-Phenyl-10-phenylethynyl-9-methylene-fluorene top
Crystal data top
C28H18F(000) = 744
Mr = 354.42Dx = 1.262 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.0901 (14) ÅCell parameters from 62 reflections
b = 5.8367 (8) Åθ = 3.5–10°
c = 23.519 (2) ŵ = 0.07 mm1
β = 105.383 (6)°T = 173 K
V = 1864.9 (4) Å3Prism, yellow
Z = 40.7 × 0.4 × 0.15 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.026
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.1°
Graphite monochromatorh = 162
ω–scansk = 60
3940 measured reflectionsl = 2727
3266 independent reflections3 standard reflections every 247 reflections
1970 reflections with I > 2s(I) intensity decay: none
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 0.82 w = 1/[σ2(Fo2) + (0.0331P)2]
where P = (Fo2 + 2Fc2)/3
3266 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.18 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.

Extra dihedral angle

-22.33 (0.18) C9 - C10 - C13 - C14

============================================================================

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

4.4375 (0.0071) x - 3.3943 (0.0025) y + 15.0442 (0.0120) z = 5.2831 (0.0038)

* 0.0007 (0.0012) C1 * 0.0299 (0.0013) C1A * -0.0180 (0.0012) C2 * 0.0117 (0.0013) C3 * 0.0005 (0.0012) C4 * -0.0151 (0.0013) C4A * -0.0098 (0.0009) C9

Rms deviation of fitted atoms = 0.0155

6.2200 (0.0075) x - 3.2006 (0.0030) y + 13.3513 (0.0089) z = 5.0639 (0.0028)

Angle to previous plane (with approximate e.s.d.) = 7.84 (0.09)

* 0.0035 (0.0012) C5 * -0.0282 (0.0013) C5A * 0.0270 (0.0014) C6 * 0.0058 (0.0013) C7 * -0.0198 (0.0013) C8 * -0.0301 (0.0013) C8A * 0.0418 (0.0010) C9

Rms deviation of fitted atoms = 0.0257

============================================================================

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.7178 (0.0117) x - 3.9107 (0.0036) y + 11.5641 (0.0174) z = 4.1590 (0.0059)

* 0.0082 (0.0004) C1A * 0.0083 (0.0004) C8A * -0.0274 (0.0013) C9 * 0.0109 (0.0005) C10

Rms deviation of fitted atoms = 0.0159

8.1684 (0.0104) x - 3.7643 (0.0040) y + 7.6752 (0.0198) z = 3.2942 (0.0080)

Angle to previous plane (with approximate e.s.d.) = 12.33 (0.14)

* 0.0079 (0.0005) C9 * -0.0216 (0.0014) C10 * 0.0070 (0.0004) C11 * 0.0066 (0.0004) C19

Rms deviation of fitted atoms = 0.0125

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
C1A0.12736 (12)0.1618 (3)0.35210 (7)0.0255 (4)
C10.04648 (12)0.1683 (3)0.37549 (7)0.0308 (4)
H10.04120.28450.40280.037*
C20.02635 (12)0.0032 (3)0.35847 (7)0.0345 (4)
H20.08220.00810.37380.041*
C30.01862 (13)0.1690 (3)0.31931 (7)0.0388 (5)
H30.06770.28470.30960.047*
C4A0.13153 (12)0.0069 (3)0.30982 (7)0.0290 (4)
C40.05982 (13)0.1743 (3)0.29423 (7)0.0368 (5)
H40.06430.29070.26680.044*
C5A0.21629 (12)0.0434 (3)0.28682 (7)0.0291 (4)
C50.25231 (14)0.0704 (3)0.24512 (7)0.0392 (5)
H50.22170.20680.22710.047*
C60.33390 (14)0.0185 (4)0.23018 (8)0.0474 (5)
H60.35970.05870.20200.057*
C70.37794 (14)0.2183 (3)0.25597 (8)0.0444 (5)
H70.43310.27780.24480.053*
C8A0.26212 (12)0.2454 (3)0.31375 (7)0.0282 (4)
C80.34287 (13)0.3330 (3)0.29791 (7)0.0357 (4)
H80.37380.46980.31550.043*
C90.21278 (11)0.3171 (3)0.35930 (7)0.0255 (4)
C100.24334 (11)0.4784 (3)0.40207 (7)0.0250 (4)
C110.32028 (12)0.6383 (3)0.40231 (7)0.0275 (4)
C120.38332 (13)0.7783 (3)0.40509 (7)0.0288 (4)
C130.46189 (12)0.9366 (3)0.40670 (7)0.0274 (4)
C140.53208 (13)0.8872 (3)0.37636 (7)0.0343 (5)
H140.52760.74870.35460.041*
C150.60805 (13)1.0385 (3)0.37779 (8)0.0381 (5)
H150.65551.00410.35690.046*
C160.61501 (13)1.2394 (3)0.40943 (7)0.0379 (5)
H160.66751.34290.41050.046*
C170.54593 (13)1.2907 (3)0.43959 (7)0.0348 (5)
H170.55101.42920.46140.042*
C180.46952 (12)1.1410 (3)0.43812 (7)0.0306 (4)
H180.42191.17760.45870.037*
C190.20326 (11)0.4918 (3)0.45495 (7)0.0245 (4)
C200.21819 (12)0.3096 (3)0.49450 (7)0.0302 (4)
H200.25310.17780.48770.036*
C210.18225 (12)0.3200 (3)0.54381 (7)0.0349 (4)
H210.19330.19590.57090.042*
C220.13056 (12)0.5095 (3)0.55381 (7)0.0361 (5)
H220.10490.51460.58730.043*
C230.11610 (13)0.6918 (3)0.51501 (7)0.0363 (5)
H230.08040.82240.52180.044*
C240.15351 (12)0.6842 (3)0.46646 (7)0.0310 (4)
H240.14510.81210.44060.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0272 (10)0.0238 (9)0.0239 (9)0.0004 (8)0.0038 (8)0.0021 (8)
C10.0316 (10)0.0304 (10)0.0295 (10)0.0026 (9)0.0062 (8)0.0001 (8)
C20.0287 (10)0.0403 (11)0.0337 (10)0.0085 (10)0.0070 (8)0.0041 (9)
C30.0413 (12)0.0373 (11)0.0332 (11)0.0144 (10)0.0021 (9)0.0008 (9)
C4A0.0322 (10)0.0277 (9)0.0235 (9)0.0027 (9)0.0009 (8)0.0023 (8)
C40.0474 (12)0.0302 (10)0.0287 (10)0.0041 (10)0.0027 (9)0.0018 (9)
C5A0.0325 (10)0.0296 (10)0.0223 (9)0.0070 (9)0.0024 (8)0.0022 (8)
C50.0471 (13)0.0402 (11)0.0293 (10)0.0058 (10)0.0085 (10)0.0046 (9)
C60.0516 (13)0.0590 (14)0.0353 (11)0.0123 (12)0.0183 (10)0.0029 (10)
C70.0411 (12)0.0620 (14)0.0330 (11)0.0015 (11)0.0148 (10)0.0023 (10)
C8A0.0288 (10)0.0325 (10)0.0221 (9)0.0043 (9)0.0046 (8)0.0058 (7)
C80.0354 (11)0.0442 (11)0.0274 (10)0.0001 (10)0.0080 (9)0.0021 (9)
C90.0261 (9)0.0257 (9)0.0242 (9)0.0009 (8)0.0058 (8)0.0039 (8)
C100.0247 (10)0.0223 (9)0.0277 (9)0.0007 (8)0.0067 (8)0.0035 (8)
C110.0286 (10)0.0291 (9)0.0251 (9)0.0006 (9)0.0079 (8)0.0026 (8)
C120.0315 (10)0.0284 (10)0.0269 (9)0.0004 (9)0.0086 (8)0.0042 (8)
C130.0269 (10)0.0276 (10)0.0262 (9)0.0017 (8)0.0042 (8)0.0044 (8)
C140.0381 (11)0.0304 (10)0.0349 (10)0.0037 (9)0.0109 (9)0.0004 (8)
C150.0331 (11)0.0440 (12)0.0407 (11)0.0040 (10)0.0160 (9)0.0048 (10)
C160.0323 (11)0.0411 (11)0.0370 (11)0.0110 (9)0.0033 (9)0.0085 (9)
C170.0384 (11)0.0309 (10)0.0311 (10)0.0077 (9)0.0019 (9)0.0004 (8)
C180.0308 (10)0.0315 (10)0.0290 (10)0.0001 (9)0.0070 (8)0.0058 (8)
C190.0226 (9)0.0238 (9)0.0261 (9)0.0071 (8)0.0048 (8)0.0028 (7)
C200.0281 (10)0.0267 (9)0.0365 (10)0.0022 (9)0.0098 (8)0.0002 (8)
C210.0326 (10)0.0391 (11)0.0339 (10)0.0062 (10)0.0104 (9)0.0065 (9)
C220.0316 (10)0.0476 (12)0.0321 (10)0.0047 (10)0.0138 (9)0.0028 (9)
C230.0315 (11)0.0370 (11)0.0410 (11)0.0031 (9)0.0109 (9)0.0079 (9)
C240.0335 (10)0.0249 (9)0.0326 (10)0.0024 (9)0.0053 (9)0.0006 (8)
Geometric parameters (Å, º) top
C1A—C11.391 (2)C10—C191.498 (2)
C1A—C4A1.412 (2)C11—C121.196 (2)
C1A—C91.480 (2)C12—C131.435 (2)
C1—C21.387 (2)C13—C181.393 (2)
C1—H10.9500C13—C141.394 (2)
C2—C31.387 (2)C14—C151.381 (2)
C2—H20.9500C14—H140.9500
C3—C41.384 (2)C15—C161.378 (2)
C3—H30.9500C15—H150.9500
C4A—C41.384 (2)C16—C171.381 (2)
C4A—C5A1.466 (2)C16—H160.9500
C4—H40.9500C17—C181.380 (2)
C5A—C51.388 (2)C17—H170.9500
C5A—C8A1.411 (2)C18—H180.9500
C5—C61.389 (2)C19—C241.388 (2)
C5—H50.9500C19—C201.392 (2)
C6—C71.383 (2)C20—C211.384 (2)
C6—H60.9500C20—H200.9500
C7—C81.387 (2)C21—C221.378 (2)
C7—H70.9500C21—H210.9500
C8A—C81.386 (2)C22—C231.381 (2)
C8A—C91.484 (2)C22—H220.9500
C8—H80.9500C23—C241.379 (2)
C9—C101.362 (2)C23—H230.9500
C10—C111.429 (2)C24—H240.9500
C1—C1A—C4A119.29 (15)C9—C10—C19122.29 (14)
C1—C1A—C9131.65 (15)C11—C10—C19114.53 (14)
C4A—C1A—C9108.85 (14)C12—C11—C10176.30 (18)
C2—C1—C1A119.19 (16)C11—C12—C13176.55 (18)
C2—C1—H1120.4C18—C13—C14118.90 (16)
C1A—C1—H1120.4C18—C13—C12121.07 (16)
C3—C2—C1120.86 (17)C14—C13—C12120.03 (15)
C3—C2—H2119.6C15—C14—C13120.37 (16)
C1—C2—H2119.6C15—C14—H14119.8
C4—C3—C2120.75 (17)C13—C14—H14119.8
C4—C3—H3119.6C16—C15—C14120.05 (17)
C2—C3—H3119.6C16—C15—H15120.0
C4—C4A—C1A121.02 (16)C14—C15—H15120.0
C4—C4A—C5A130.78 (16)C15—C16—C17120.20 (17)
C1A—C4A—C5A108.09 (15)C15—C16—H16119.9
C4A—C4—C3118.73 (17)C17—C16—H16119.9
C4A—C4—H4120.6C18—C17—C16120.11 (17)
C3—C4—H4120.6C18—C17—H17119.9
C5—C5A—C8A120.51 (16)C16—C17—H17119.9
C5—C5A—C4A130.66 (16)C17—C18—C13120.37 (16)
C8A—C5A—C4A108.82 (14)C17—C18—H18119.8
C5A—C5—C6118.86 (18)C13—C18—H18119.8
C5A—C5—H5120.6C24—C19—C20118.84 (15)
C6—C5—H5120.6C24—C19—C10121.68 (14)
C7—C6—C5120.60 (18)C20—C19—C10119.46 (15)
C7—C6—H6119.7C21—C20—C19120.15 (16)
C5—C6—H6119.7C21—C20—H20119.9
C6—C7—C8121.07 (18)C19—C20—H20119.9
C6—C7—H7119.5C22—C21—C20120.38 (17)
C8—C7—H7119.5C22—C21—H21119.8
C8—C8A—C5A119.91 (16)C20—C21—H21119.8
C8—C8A—C9131.71 (16)C21—C22—C23119.82 (16)
C5A—C8A—C9108.27 (14)C21—C22—H22120.1
C8A—C8—C7119.05 (18)C23—C22—H22120.1
C8A—C8—H8120.5C24—C23—C22120.02 (17)
C7—C8—H8120.5C24—C23—H23120.0
C10—C9—C1A126.60 (15)C22—C23—H23120.0
C10—C9—C8A127.70 (15)C23—C24—C19120.74 (16)
C1A—C9—C8A105.50 (13)C23—C24—H24119.6
C9—C10—C11123.05 (15)C19—C24—H24119.6
C4A—C1A—C1—C22.6 (2)C4A—C1A—C9—C8A6.09 (17)
C9—C1A—C1—C2176.66 (16)C8—C8A—C9—C107.9 (3)
C1A—C1—C2—C30.9 (2)C5A—C8A—C9—C10168.06 (16)
C1—C2—C3—C42.9 (3)C8—C8A—C9—C1A177.02 (16)
C1—C1A—C4A—C44.3 (2)C5A—C8A—C9—C1A7.02 (17)
C9—C1A—C4A—C4179.60 (14)C1A—C9—C10—C11173.09 (15)
C1—C1A—C4A—C5A172.39 (14)C8A—C9—C10—C1112.8 (3)
C9—C1A—C4A—C5A2.95 (17)C1A—C9—C10—C1911.1 (2)
C1A—C4A—C4—C32.3 (2)C8A—C9—C10—C19162.94 (15)
C5A—C4A—C4—C3173.46 (16)C18—C13—C14—C150.3 (2)
C2—C3—C4—C4A1.2 (2)C12—C13—C14—C15179.87 (15)
C4—C4A—C5A—C54.2 (3)C13—C14—C15—C160.2 (3)
C1A—C4A—C5A—C5179.56 (17)C14—C15—C16—C170.3 (3)
C4—C4A—C5A—C8A174.65 (17)C15—C16—C17—C180.1 (3)
C1A—C4A—C5A—C8A1.57 (17)C16—C17—C18—C130.5 (2)
C8A—C5A—C5—C60.3 (2)C14—C13—C18—C170.6 (2)
C4A—C5A—C5—C6178.47 (16)C12—C13—C18—C17179.52 (15)
C5A—C5—C6—C70.6 (3)C9—C10—C19—C24118.75 (18)
C5—C6—C7—C80.9 (3)C11—C10—C19—C2465.2 (2)
C5—C5A—C8A—C80.9 (2)C9—C10—C19—C2062.9 (2)
C4A—C5A—C8A—C8178.06 (15)C11—C10—C19—C20113.19 (17)
C5—C5A—C8A—C9175.58 (15)C24—C19—C20—C211.1 (2)
C4A—C5A—C8A—C95.41 (17)C10—C19—C20—C21179.52 (15)
C5A—C8A—C8—C70.6 (2)C19—C20—C21—C220.7 (2)
C9—C8A—C8—C7174.93 (17)C20—C21—C22—C231.2 (3)
C6—C7—C8—C8A0.3 (3)C21—C22—C23—C240.1 (3)
C1—C1A—C9—C1016.4 (3)C22—C23—C24—C192.0 (3)
C4A—C1A—C9—C10169.07 (15)C20—C19—C24—C232.5 (2)
C1—C1A—C9—C8A168.47 (16)C10—C19—C24—C23179.17 (15)
 

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