9-Methyl­ene-10,10-bis­(phenyl­ethyn­yl)fluorene

In the title compound, C₃₀H₁₈, the fluorene moiety displays normal dimensions, such as a narrow ring angle of 105.3 (3)° at the 9-position, the atom bearing the exocyclic double bond. The phen­yl rings subtend angles of 14.8 (2) and 3.9 (2)° to the fluorene plane. Mol­ecules are stacked parallel to the short c axis of 4.001 (1) Å.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.126
• Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.39
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C11    ...       1.44 Ang.
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    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C12'   -   C13'   ...       1.44 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           25.06
           From the CIF: _reflns_number_total               2004
           Count of symmetry unique reflns         2011
           Completeness (_total/calc)             99.65%
           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
   8 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: P3 (Nicolet, 1987); cell refinement: P3; data reduction: XDISK (Nicolet, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

9-Methylene-10,10-bis(phenylethynyl)fluorene

Crystal data

C30H18	Dx = 1.284 Mg m^−3
Mr = 378.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 50 reflections
a = 25.824 (9) Å	θ = 10–11.5°
b = 18.944 (8) Å	µ = 0.07 mm^−1
c = 4.001 (1) Å	T = 173 K
V = 1957.3 (12) Å^3	Prism, yellow
Z = 4	0.64 × 0.22 × 0.18 mm
F(000) = 792

Data collection

Siemens R3 diffractometer	Rint = 0.066
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 3.2°
Graphite monochromator	h = −30→30
ω scans	k = −22→22
6350 measured reflections	l = 0→4
2004 independent reflections	3 standard reflections every 147 reflections
1320 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0598P)^2] where P = (Fo^2 + 2Fc^2)/3
2004 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.21 e Å^−3
285 restraints	Δρmin = −0.22 e Å^−3

Special details

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.

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

8.4000 (0.0440) x - 5.9065 (0.0319) y + 3.5718 (0.0036) z = 0.8779 (0.0230)

* -0.0044 (0.0030) C13 * 0.0036 (0.0030) C14 * 0.0024 (0.0029) C15 * -0.0075 (0.0031) C16 * 0.0066 (0.0032) C17 * -0.0007 (0.0031) C18

Rms deviation of fitted atoms = 0.0048

12.3509 (0.0215) x - 1.9894 (0.0121) y + 3.4885 (0.0024) z = 5.0351 (0.0089)

Angle to previous plane (with approximate e.s.d.) = 14.83 (0.15)

* 0.0435 (0.0036) C1 * -0.0178 (0.0034) C1A * 0.0521 (0.0036) C2 * 0.0222 (0.0035) C3 * -0.0166 (0.0037) C4 * -0.0473 (0.0038) C4A * -0.0280 (0.0038) C5 * -0.0477 (0.0038) C5A * 0.0314 (0.0035) C6 * 0.0636 (0.0036) C7 * 0.0315 (0.0035) C8 * -0.0329 (0.0037) C8A * -0.0539 (0.0032) C9

Rms deviation of fitted atoms = 0.0402

11.8786 (0.0398) x - 0.7654 (0.0321) y + 3.5489 (0.0035) z = 5.4197 (0.0348)

Angle to previous plane (with approximate e.s.d.) = 3.94 (0.17)

* 0.0123 (0.0030) C13' * -0.0081 (0.0032) C14' * -0.0013 (0.0033) C15' * 0.0064 (0.0031) C16' * -0.0020 (0.0030) C17' * -0.0074 (0.0030) C18'

Rms deviation of fitted atoms = 0.0073

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

Pseudo-torsion angles:

10.04 (0.44) C9 - C10 - C13 - C14 - 4.73 (0.44) C9 - C10 - C13' - C14'

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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.34117 (12)	0.80376 (18)	0.6887 (10)	0.0324 (9)
C1	0.37149 (14)	0.86291 (18)	0.6327 (12)	0.0408 (10)
H1	0.4041	0.8588	0.5249	0.049*
C2	0.35326 (15)	0.92867 (18)	0.7372 (11)	0.0451 (10)
H2	0.3735	0.9696	0.6965	0.054*
C3	0.30595 (15)	0.9351 (2)	0.8998 (11)	0.0464 (10)
H3	0.2943	0.9804	0.9687	0.056*
C4	0.27568 (15)	0.8764 (2)	0.9624 (11)	0.0453 (11)
H4	0.2436	0.8807	1.0768	0.054*
C4A	0.29324 (13)	0.81047 (18)	0.8538 (10)	0.0364 (9)
C5A	0.27044 (13)	0.73986 (18)	0.8941 (10)	0.0366 (9)
C5	0.22494 (14)	0.7190 (2)	1.0490 (12)	0.0445 (10)
H5	0.2020	0.7529	1.1418	0.053*
C6	0.21344 (14)	0.6473 (2)	1.0658 (11)	0.0471 (11)
H6	0.1825	0.6319	1.1718	0.057*
C7	0.24712 (14)	0.5984 (2)	0.9279 (11)	0.0447 (10)
H7	0.2389	0.5496	0.9423	0.054*
C8	0.29272 (13)	0.61867 (19)	0.7688 (11)	0.0390 (9)
H8	0.3154	0.5844	0.6753	0.047*
C8A	0.30433 (13)	0.69047 (18)	0.7502 (10)	0.0334 (8)
C9	0.34942 (12)	0.72813 (17)	0.6060 (10)	0.0325 (8)
C10	0.38960 (12)	0.70004 (17)	0.4275 (10)	0.0328 (9)
C11	0.39264 (12)	0.62645 (18)	0.3437 (11)	0.0337 (9)
C12	0.39649 (13)	0.56679 (18)	0.2479 (11)	0.0369 (9)
C13	0.39706 (13)	0.49517 (18)	0.1296 (11)	0.0368 (9)
C14	0.35269 (14)	0.45300 (18)	0.1664 (11)	0.0402 (10)
H14	0.3225	0.4717	0.2699	0.048*
C15	0.35315 (15)	0.38410 (19)	0.0511 (11)	0.0428 (10)
H15	0.3231	0.3556	0.0762	0.051*
C16	0.39677 (15)	0.35634 (19)	−0.1002 (11)	0.0455 (10)
H16	0.3964	0.3092	−0.1817	0.055*
C17	0.44102 (15)	0.39708 (19)	−0.1329 (12)	0.0472 (11)
H17	0.4712	0.3775	−0.2321	0.057*
C18	0.44129 (14)	0.46677 (19)	−0.0203 (11)	0.0416 (10)
H18	0.4715	0.4949	−0.0455	0.050*
C11'	0.43049 (13)	0.74157 (18)	0.2900 (11)	0.0344 (9)
C12'	0.46466 (13)	0.77370 (18)	0.1565 (11)	0.0341 (9)
C13'	0.50500 (12)	0.81704 (18)	0.0165 (10)	0.0337 (8)
C14'	0.50166 (14)	0.89057 (18)	0.0378 (12)	0.0425 (10)
H14'	0.4721	0.9120	0.1362	0.051*
C15'	0.54127 (15)	0.9320 (2)	−0.0839 (12)	0.0510 (11)
H15'	0.5391	0.9819	−0.0659	0.061*
C16'	0.58392 (15)	0.9018 (2)	−0.2310 (12)	0.0479 (11)
H16'	0.6111	0.9309	−0.3125	0.057*
C17'	0.58760 (14)	0.8292 (2)	−0.2614 (11)	0.0447 (10)
H17'	0.6170	0.8084	−0.3648	0.054*
C18'	0.54805 (12)	0.78719 (19)	−0.1395 (11)	0.0385 (9)
H18'	0.5502	0.7374	−0.1625	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0333 (19)	0.0322 (18)	0.032 (2)	0.0012 (15)	−0.0068 (17)	−0.0014 (18)
C1	0.045 (2)	0.035 (2)	0.043 (2)	−0.0008 (17)	0.000 (2)	−0.002 (2)
C2	0.058 (2)	0.032 (2)	0.046 (3)	0.0006 (18)	−0.004 (2)	−0.001 (2)
C3	0.058 (2)	0.039 (2)	0.042 (2)	0.0138 (18)	−0.002 (2)	−0.003 (2)
C4	0.044 (2)	0.048 (2)	0.044 (3)	0.0114 (17)	−0.002 (2)	−0.003 (2)
C4A	0.0387 (19)	0.0378 (19)	0.033 (2)	0.0033 (16)	−0.0050 (18)	−0.002 (2)
C5A	0.0339 (18)	0.044 (2)	0.032 (2)	−0.0021 (16)	−0.0038 (18)	−0.002 (2)
C5	0.040 (2)	0.055 (2)	0.038 (2)	0.0010 (18)	0.001 (2)	0.001 (2)
C6	0.038 (2)	0.066 (3)	0.038 (3)	−0.0073 (19)	−0.001 (2)	0.004 (2)
C7	0.047 (2)	0.049 (2)	0.038 (2)	−0.0116 (18)	−0.006 (2)	0.003 (2)
C8	0.040 (2)	0.042 (2)	0.035 (2)	−0.0036 (16)	−0.006 (2)	0.003 (2)
C8A	0.0346 (18)	0.036 (2)	0.030 (2)	−0.0002 (15)	−0.0049 (17)	0.0014 (19)
C9	0.0326 (18)	0.0335 (19)	0.031 (2)	0.0011 (15)	−0.0037 (17)	−0.0028 (18)
C10	0.0330 (18)	0.0282 (19)	0.037 (2)	−0.0006 (15)	−0.0063 (18)	0.0013 (18)
C11	0.0299 (17)	0.0308 (19)	0.041 (2)	−0.0012 (14)	−0.0015 (18)	0.0007 (19)
C12	0.0333 (18)	0.035 (2)	0.042 (2)	0.0004 (15)	−0.005 (2)	−0.002 (2)
C13	0.0438 (19)	0.0289 (18)	0.038 (2)	0.0021 (16)	−0.002 (2)	0.0033 (19)
C14	0.039 (2)	0.0331 (19)	0.048 (3)	0.0014 (16)	0.005 (2)	−0.006 (2)
C15	0.052 (2)	0.035 (2)	0.041 (2)	−0.0013 (18)	−0.002 (2)	−0.003 (2)
C16	0.063 (2)	0.032 (2)	0.042 (2)	0.0043 (18)	−0.006 (2)	−0.004 (2)
C17	0.047 (2)	0.047 (2)	0.047 (3)	0.0132 (18)	0.001 (2)	−0.009 (2)
C18	0.042 (2)	0.041 (2)	0.042 (3)	0.0018 (17)	0.002 (2)	−0.005 (2)
C11'	0.0340 (19)	0.0302 (19)	0.039 (2)	0.0027 (15)	−0.0036 (18)	−0.0011 (19)
C12'	0.0353 (19)	0.033 (2)	0.034 (2)	0.0009 (16)	−0.0032 (18)	−0.0044 (19)
C13'	0.0331 (18)	0.034 (2)	0.034 (2)	−0.0031 (15)	−0.0057 (18)	0.0018 (18)
C14'	0.0372 (19)	0.032 (2)	0.058 (3)	−0.0001 (16)	−0.004 (2)	−0.002 (2)
C15'	0.054 (2)	0.039 (2)	0.060 (3)	−0.0062 (18)	−0.007 (2)	0.010 (2)
C16'	0.043 (2)	0.051 (2)	0.050 (3)	−0.0136 (19)	−0.005 (2)	0.013 (2)
C17'	0.040 (2)	0.053 (2)	0.041 (3)	−0.0045 (18)	0.001 (2)	0.002 (2)
C18'	0.0382 (19)	0.034 (2)	0.043 (2)	−0.0001 (15)	−0.004 (2)	0.002 (2)

Geometric parameters (Å, º)

C1A—C1	1.385 (4)	C11'—C12'	1.198 (5)
C1A—C4A	1.409 (5)	C12'—C13'	1.440 (5)
C1A—C9	1.486 (5)	C13'—C18'	1.395 (5)
C1—C2	1.396 (5)	C13'—C14'	1.398 (4)
C2—C3	1.389 (5)	C14'—C15'	1.378 (5)
C3—C4	1.383 (5)	C15'—C16'	1.374 (5)
C4—C4A	1.398 (5)	C16'—C17'	1.385 (5)
C4A—C5A	1.470 (5)	C17'—C18'	1.383 (5)
C5A—C5	1.386 (5)	C1—H1	0.9500
C5A—C8A	1.405 (5)	C2—H2	0.9500
C5—C6	1.392 (5)	C3—H3	0.9500
C6—C7	1.385 (5)	C4—H4	0.9500
C7—C8	1.392 (5)	C5—H5	0.9500
C8—C8A	1.395 (5)	C6—H6	0.9500
C8A—C9	1.482 (5)	C7—H7	0.9500
C9—C10	1.367 (5)	C8—H8	0.9500
C10—C11'	1.427 (5)	C14—H14	0.9500
C10—C11	1.436 (5)	C15—H15	0.9500
C11—C12	1.197 (4)	C16—H16	0.9500
C12—C13	1.437 (5)	C17—H17	0.9500
C13—C18	1.398 (5)	C18—H18	0.9500
C13—C14	1.405 (4)	C14'—H14'	0.9500
C14—C15	1.384 (5)	C15'—H15'	0.9500
C15—C16	1.383 (5)	C16'—H16'	0.9500
C16—C17	1.385 (5)	C17'—H17'	0.9500
C17—C18	1.395 (5)	C18'—H18'	0.9500
C1—C1A—C4A	120.0 (3)	C15'—C14'—C13'	120.0 (4)
C1—C1A—C9	131.5 (3)	C16'—C15'—C14'	120.6 (4)
C4A—C1A—C9	108.5 (3)	C15'—C16'—C17'	120.5 (4)
C1A—C1—C2	118.9 (4)	C18'—C17'—C16'	119.3 (4)
C3—C2—C1	121.0 (4)	C17'—C18'—C13'	120.9 (3)
C4—C3—C2	120.7 (4)	C1A—C1—H1	120.6
C3—C4—C4A	118.6 (4)	C2—C1—H1	120.6
C4—C4A—C1A	120.8 (3)	C3—C2—H2	119.5
C4—C4A—C5A	130.4 (3)	C1—C2—H2	119.5
C1A—C4A—C5A	108.7 (3)	C4—C3—H3	119.6
C5—C5A—C8A	121.4 (3)	C2—C3—H3	119.6
C5—C5A—C4A	130.4 (3)	C3—C4—H4	120.7
C8A—C5A—C4A	108.2 (3)	C4A—C4—H4	120.7
C5A—C5—C6	118.8 (4)	C5A—C5—H5	120.6
C7—C6—C5	119.9 (4)	C6—C5—H5	120.6
C6—C7—C8	121.9 (3)	C7—C6—H6	120.0
C7—C8—C8A	118.4 (4)	C5—C6—H6	120.0
C8—C8A—C5A	119.6 (3)	C6—C7—H7	119.0
C8—C8A—C9	131.2 (3)	C8—C7—H7	119.0
C5A—C8A—C9	109.2 (3)	C7—C8—H8	120.8
C10—C9—C8A	127.7 (3)	C8A—C8—H8	120.8
C10—C9—C1A	126.9 (3)	C15—C14—H14	120.2
C8A—C9—C1A	105.3 (3)	C13—C14—H14	120.2
C9—C10—C11'	123.3 (3)	C16—C15—H15	119.6
C9—C10—C11	122.8 (3)	C14—C15—H15	119.6
C11'—C10—C11	113.9 (3)	C15—C16—H16	120.0
C12—C11—C10	174.6 (4)	C17—C16—H16	120.0
C11—C12—C13	175.8 (4)	C16—C17—H17	120.0
C18—C13—C14	119.5 (3)	C18—C17—H17	120.0
C18—C13—C12	120.9 (3)	C17—C18—H18	120.0
C14—C13—C12	119.6 (3)	C13—C18—H18	120.0
C15—C14—C13	119.6 (4)	C15'—C14'—H14'	120.0
C16—C15—C14	120.8 (4)	C13'—C14'—H14'	120.0
C15—C16—C17	120.1 (4)	C16'—C15'—H15'	119.7
C16—C17—C18	120.1 (4)	C14'—C15'—H15'	119.7
C17—C18—C13	119.9 (4)	C15'—C16'—H16'	119.8
C12'—C11'—C10	175.8 (4)	C17'—C16'—H16'	119.8
C11'—C12'—C13'	175.1 (4)	C18'—C17'—H17'	120.3
C18'—C13'—C14'	118.7 (3)	C16'—C17'—H17'	120.3
C18'—C13'—C12'	121.3 (3)	C17'—C18'—H18'	119.6
C14'—C13'—C12'	120.0 (3)	C13'—C18'—H18'	119.6
C4A—C1A—C1—C2	−1.1 (6)	C5A—C8A—C9—C10	−176.0 (4)
C9—C1A—C1—C2	179.4 (4)	C8—C8A—C9—C1A	−175.5 (4)
C1A—C1—C2—C3	1.1 (6)	C5A—C8A—C9—C1A	2.6 (4)
C1—C2—C3—C4	0.0 (6)	C1—C1A—C9—C10	−4.8 (7)
C2—C3—C4—C4A	−1.0 (6)	C4A—C1A—C9—C10	175.6 (4)
C3—C4—C4A—C1A	1.0 (6)	C1—C1A—C9—C8A	176.6 (4)
C3—C4—C4A—C5A	177.8 (4)	C4A—C1A—C9—C8A	−3.0 (4)
C1—C1A—C4A—C4	0.1 (6)	C8A—C9—C10—C11'	177.9 (4)
C9—C1A—C4A—C4	179.7 (4)	C1A—C9—C10—C11'	−0.4 (6)
C1—C1A—C4A—C5A	−177.4 (4)	C8A—C9—C10—C11	2.0 (6)
C9—C1A—C4A—C5A	2.3 (4)	C1A—C9—C10—C11	−176.3 (4)
C4—C4A—C5A—C5	0.6 (7)	C12—C13—C14—C15	179.7 (4)
C1A—C4A—C5A—C5	177.7 (4)	C13—C14—C15—C16	0.0 (6)
C4—C4A—C5A—C8A	−177.7 (4)	C14—C15—C16—C17	1.1 (6)
C1A—C4A—C5A—C8A	−0.6 (4)	C15—C16—C17—C18	−1.5 (7)
C8A—C5A—C5—C6	1.1 (6)	C16—C17—C18—C13	0.8 (7)
C4A—C5A—C5—C6	−176.9 (4)	C14—C13—C18—C17	0.2 (6)
C5A—C5—C6—C7	−0.3 (6)	C12—C13—C18—C17	179.9 (4)
C5—C6—C7—C8	−0.3 (7)	C18'—C13'—C14'—C15'	−2.2 (7)
C6—C7—C8—C8A	0.1 (6)	C12'—C13'—C14'—C15'	177.3 (4)
C7—C8—C8A—C5A	0.7 (6)	C13'—C14'—C15'—C16'	0.9 (7)
C7—C8—C8A—C9	178.7 (4)	C14'—C15'—C16'—C17'	0.5 (7)
C5—C5A—C8A—C8	−1.4 (6)	C15'—C16'—C17'—C18'	−0.5 (7)
C4A—C5A—C8A—C8	177.1 (4)	C16'—C17'—C18'—C13'	−0.8 (6)
C5—C5A—C8A—C9	−179.7 (4)	C14'—C13'—C18'—C17'	2.1 (6)
C4A—C5A—C8A—C9	−1.3 (4)	C12'—C13'—C18'—C17'	−177.4 (4)
C8—C8A—C9—C10	5.9 (7)