9-(p-Methyl­phenyl)­fluorene

The title compound, C₂₀H₁₆, displays no unusual structural characteristics. The aryl and fluorenyl ring planes form an angle of 78.26 (14)°. Neither intermolecular hydrogen bonding nor aryl–H...π(arene) interactions are exhibited, which conforms with the rapid recrystallization of the melted crystals on cooling.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.038
• wR factor = 0.117
• Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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           25.60
           From the CIF: _reflns_number_total               1489
           Count of symmetry unique reflns         1506
           Completeness (_total/calc)             98.87%
           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
   0 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

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: TEXSAN, SHELXL97, and PLATON (Spek, 2003).

9-(p-Methylphenyl)fluorene

Crystal data

C20H16	F(000) = 272
Mr = 256.33	Dx = 1.175 Mg m^−3
Monoclinic, P21	Melting point = 397–398 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71069 Å
a = 9.8828 (19) Å	Cell parameters from 25 reflections
b = 5.8836 (17) Å	θ = 10.1–13.5°
c = 12.5231 (12) Å	µ = 0.07 mm^−1
β = 95.684 (10)°	T = 296 K
V = 724.6 (3) Å^3	Elongated prism, colorless
Z = 2	0.38 × 0.18 × 0.15 mm

Data collection

Rigaku AFC-5S diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 25.6°, θmin = 2.1°
Graphite monochromator	h = 0→11
ω scans	k = 0→7
1577 measured reflections	l = −15→15
1489 independent reflections	3 standard reflections every 100 reflections
881 reflections with I > 2σ(I)	intensity decay: 0.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0538P)^2 + 0.0314P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1489 reflections	Δρmax = 0.14 e Å^−3
182 parameters	Δρmin = −0.14 e Å^−3
1 restraint	Absolute structure: The absolute configuration could not be determined because of the lack of heavy atoms
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1649 (3)	0.4220 (8)	0.5056 (3)	0.0605 (10)
C2	0.1640 (4)	0.5755 (9)	0.5899 (3)	0.0713 (12)
C3	0.2468 (4)	0.7645 (9)	0.5952 (3)	0.0732 (13)
C4	0.3309 (4)	0.8089 (8)	0.5167 (3)	0.0637 (10)
C4A	0.3321 (3)	0.6553 (7)	0.4321 (3)	0.0512 (9)
C4B	0.4104 (3)	0.6559 (7)	0.3387 (3)	0.0541 (9)
C5	0.5077 (4)	0.8060 (9)	0.3092 (3)	0.0720 (12)
C6	0.5649 (4)	0.7653 (11)	0.2154 (4)	0.0884 (16)
C7	0.5289 (4)	0.5781 (11)	0.1527 (3)	0.0845 (15)
C8	0.4332 (4)	0.4238 (9)	0.1824 (3)	0.0700 (12)
C8A	0.3741 (3)	0.4643 (7)	0.2766 (3)	0.0514 (9)
C9	0.2690 (3)	0.3235 (7)	0.3282 (2)	0.0492 (8)
C9A	0.2491 (3)	0.4623 (7)	0.4268 (2)	0.0506 (9)
C10	0.1420 (3)	0.2760 (7)	0.2535 (2)	0.0480 (9)
C11	0.1257 (4)	0.0722 (7)	0.1998 (3)	0.0596 (10)
C12	0.0116 (4)	0.0296 (7)	0.1286 (3)	0.0645 (11)
C13	−0.0881 (4)	0.1898 (8)	0.1081 (3)	0.0605 (11)
C14	−0.0728 (4)	0.3942 (8)	0.1617 (3)	0.0601 (11)
C15	0.0412 (3)	0.4366 (7)	0.2337 (3)	0.0540 (9)
C16	−0.2119 (4)	0.1435 (11)	0.0304 (3)	0.0862 (15)
H1	0.1095	0.2940	0.5027	0.073*
H2	0.1068	0.5504	0.6433	0.086*
H3	0.2458	0.8636	0.6530	0.088*
H4	0.3854	0.9380	0.5198	0.076*
H5	0.5337	0.9312	0.3517	0.086*
H6	0.6293	0.8662	0.1938	0.106*
H7	0.5694	0.5550	0.0896	0.101*
H8	0.4093	0.2969	0.1403	0.084*
H9	0.3105	0.1780	0.3511	0.059*
H11	0.1923	−0.0392	0.2115	0.071*
H12	0.0029	−0.1105	0.0941	0.077*
H14	−0.1395	0.5053	0.1497	0.072*
H15	0.0493	0.5757	0.2689	0.065*
H16A	−0.1935	0.0189	−0.0155	0.129*
H16B	−0.2334	0.2764	−0.0124	0.129*
H16C	−0.2875	0.1058	0.0697	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.055 (2)	0.077 (3)	0.0493 (19)	−0.002 (2)	0.0021 (17)	0.002 (2)
C2	0.061 (2)	0.099 (4)	0.055 (2)	0.010 (3)	0.0080 (19)	−0.005 (3)
C3	0.074 (3)	0.085 (3)	0.060 (2)	0.012 (3)	−0.002 (2)	−0.021 (2)
C4	0.059 (2)	0.056 (2)	0.072 (2)	0.001 (2)	−0.0126 (19)	−0.008 (2)
C4A	0.0475 (19)	0.052 (2)	0.0518 (19)	0.002 (2)	−0.0068 (15)	−0.0009 (19)
C4B	0.0374 (17)	0.063 (2)	0.060 (2)	0.004 (2)	−0.0043 (16)	0.011 (2)
C5	0.053 (2)	0.079 (3)	0.084 (3)	−0.006 (3)	0.001 (2)	0.017 (3)
C6	0.056 (3)	0.108 (5)	0.103 (3)	−0.006 (3)	0.014 (3)	0.036 (4)
C7	0.061 (3)	0.126 (5)	0.069 (3)	0.012 (3)	0.016 (2)	0.021 (3)
C8	0.057 (2)	0.095 (3)	0.059 (2)	0.013 (3)	0.0064 (17)	0.002 (3)
C8A	0.0412 (18)	0.062 (3)	0.0491 (18)	0.0100 (19)	−0.0038 (14)	0.0052 (19)
C9	0.0502 (18)	0.047 (2)	0.0496 (18)	0.0062 (18)	0.0003 (14)	0.0024 (18)
C9A	0.0455 (17)	0.060 (2)	0.0449 (18)	0.007 (2)	−0.0026 (15)	−0.0021 (19)
C10	0.0546 (19)	0.049 (2)	0.0402 (17)	0.0025 (19)	0.0052 (15)	−0.0001 (18)
C11	0.065 (2)	0.053 (2)	0.060 (2)	0.008 (2)	−0.0004 (19)	−0.007 (2)
C12	0.082 (3)	0.057 (3)	0.054 (2)	−0.011 (2)	0.002 (2)	−0.014 (2)
C13	0.061 (2)	0.076 (3)	0.044 (2)	−0.014 (2)	0.0057 (17)	0.005 (2)
C14	0.050 (2)	0.069 (3)	0.061 (2)	0.007 (2)	0.0017 (17)	0.007 (2)
C15	0.059 (2)	0.044 (2)	0.057 (2)	−0.001 (2)	−0.0009 (16)	−0.002 (2)
C16	0.072 (3)	0.121 (4)	0.062 (2)	−0.027 (3)	−0.0059 (19)	−0.001 (3)

Geometric parameters (Å, º)

C1—C9A	1.373 (5)	C13—C14	1.378 (6)
C1—C2	1.389 (6)	C13—C16	1.511 (5)
C2—C3	1.378 (6)	C14—C15	1.393 (5)
C3—C4	1.374 (6)	C1—H1	0.9300
C4—C4A	1.393 (5)	C2—H2	0.9300
C4A—C9A	1.399 (5)	C3—H3	0.9300
C4A—C4B	1.465 (5)	C4—H4	0.9300
C4B—C5	1.382 (5)	C5—H5	0.9300
C4B—C8A	1.396 (5)	C6—H6	0.9300
C5—C6	1.374 (6)	C7—H7	0.9300
C6—C7	1.379 (7)	C8—H8	0.9300
C7—C8	1.389 (7)	C9—H9	0.9800
C8—C8A	1.389 (5)	C11—H11	0.9300
C8A—C9	1.521 (5)	C12—H12	0.9300
C9—C9A	1.510 (5)	C14—H14	0.9300
C9—C10	1.516 (4)	C15—H15	0.9300
C10—C11	1.377 (5)	C16—H16A	0.9600
C10—C15	1.377 (5)	C16—H16B	0.9600
C11—C12	1.389 (5)	C16—H16C	0.9600
C12—C13	1.370 (6)
C9A—C1—C2	118.9 (4)	C9A—C1—H1	120.5
C3—C2—C1	120.8 (4)	C2—C1—H1	120.5
C4—C3—C2	121.1 (4)	C3—C2—H2	119.6
C3—C4—C4A	118.2 (4)	C1—C2—H2	119.6
C4—C4A—C9A	120.9 (3)	C4—C3—H3	119.4
C4—C4A—C4B	130.6 (4)	C2—C3—H3	119.4
C9A—C4A—C4B	108.5 (3)	C3—C4—H4	120.9
C5—C4B—C8A	120.9 (4)	C4A—C4—H4	120.9
C5—C4B—C4A	130.7 (4)	C6—C5—H5	120.9
C8A—C4B—C4A	108.4 (3)	C4B—C5—H5	120.9
C6—C5—C4B	118.3 (5)	C5—C6—H6	119.3
C5—C6—C7	121.4 (4)	C7—C6—H6	119.3
C6—C7—C8	120.9 (4)	C6—C7—H7	119.5
C8A—C8—C7	118.1 (5)	C8—C7—H7	119.5
C8—C8A—C4B	120.4 (4)	C8A—C8—H8	121.0
C8—C8A—C9	129.0 (4)	C7—C8—H8	121.0
C4B—C8A—C9	110.6 (3)	C9A—C9—H9	108.5
C9A—C9—C10	115.9 (3)	C10—C9—H9	108.5
C9A—C9—C8A	101.7 (3)	C8A—C9—H9	108.5
C10—C9—C8A	113.4 (3)	C10—C11—H11	119.4
C1—C9A—C4A	120.0 (3)	C12—C11—H11	119.4
C1—C9A—C9	129.2 (3)	C13—C12—H12	119.4
C4A—C9A—C9	110.8 (3)	C11—C12—H12	119.4
C11—C10—C15	117.5 (3)	C13—C14—H14	119.5
C11—C10—C9	120.8 (3)	C15—C14—H14	119.5
C15—C10—C9	121.7 (3)	C10—C15—H15	119.4
C10—C11—C12	121.3 (4)	C14—C15—H15	119.4
C13—C12—C11	121.3 (4)	C13—C16—H16A	109.5
C12—C13—C14	117.9 (3)	C13—C16—H16B	109.5
C12—C13—C16	121.2 (4)	H16A—C16—H16B	109.5
C14—C13—C16	120.9 (4)	C13—C16—H16C	109.5
C13—C14—C15	120.9 (4)	H16A—C16—H16C	109.5
C10—C15—C14	121.2 (4)	H16B—C16—H16C	109.5
C9A—C1—C2—C3	−0.6 (6)	C2—C1—C9A—C4A	0.1 (5)
C1—C2—C3—C4	1.2 (6)	C2—C1—C9A—C9	179.9 (4)
C2—C3—C4—C4A	−1.2 (6)	C4—C4A—C9A—C1	−0.1 (5)
C3—C4—C4A—C9A	0.6 (5)	C4B—C4A—C9A—C1	180.0 (3)
C3—C4—C4A—C4B	−179.4 (4)	C4—C4A—C9A—C9	−179.9 (3)
C4—C4A—C4B—C5	1.7 (6)	C4B—C4A—C9A—C9	0.1 (4)
C9A—C4A—C4B—C5	−178.3 (4)	C10—C9—C9A—C1	56.2 (5)
C4—C4A—C4B—C8A	−179.5 (4)	C8A—C9—C9A—C1	179.6 (3)
C9A—C4A—C4B—C8A	0.4 (4)	C10—C9—C9A—C4A	−124.0 (3)
C8A—C4B—C5—C6	1.9 (5)	C8A—C9—C9A—C4A	−0.6 (4)
C4A—C4B—C5—C6	−179.5 (4)	C9A—C9—C10—C11	−144.4 (3)
C4B—C5—C6—C7	−1.2 (6)	C8A—C9—C10—C11	98.5 (4)
C5—C6—C7—C8	0.0 (7)	C9A—C9—C10—C15	37.9 (5)
C6—C7—C8—C8A	0.4 (6)	C8A—C9—C10—C15	−79.2 (4)
C7—C8—C8A—C4B	0.3 (5)	C15—C10—C11—C12	−0.2 (5)
C7—C8—C8A—C9	−179.2 (4)	C9—C10—C11—C12	−177.9 (3)
C5—C4B—C8A—C8	−1.4 (5)	C10—C11—C12—C13	0.8 (6)
C4A—C4B—C8A—C8	179.7 (3)	C11—C12—C13—C14	−0.9 (6)
C5—C4B—C8A—C9	178.1 (3)	C11—C12—C13—C16	179.9 (3)
C4A—C4B—C8A—C9	−0.8 (4)	C12—C13—C14—C15	0.6 (5)
C8—C8A—C9—C9A	−179.7 (3)	C16—C13—C14—C15	179.8 (3)
C4B—C8A—C9—C9A	0.8 (3)	C11—C10—C15—C14	−0.2 (5)
C8—C8A—C9—C10	−54.5 (5)	C9—C10—C15—C14	177.5 (3)
C4B—C8A—C9—C10	126.0 (3)	C13—C14—C15—C10	0.0 (5)