7-(4-Fluoro­phen­yl)-8H-benzo[h]indeno[1,2-b]quinolin-8-one

The title compound, C₂₆H₁₄FNO, was synthesized by the reaction of 4-fluoro­benzaldehyde, 1-naphthyl­amine and 1,3-indanedione in glycol under microwave irradiation. The fused ring system is approximately planar and the attached fluoro­phenyl ring forms a dihedral angle of 65.21 (8)°. The mol­ecules are linked by inter­molecular C—H...O hydrogen bonds and π–π inter­actions, forming a chain structure

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.089
• Data-to-parameter ratio = 6.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.68
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           25.00
           From the CIF: _reflns_number_total               1751
           Count of symmetry unique reflns         1755
           Completeness (_total/calc)             99.77%
           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
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

7-(4-fluorophenyl)-8H-benzo[h]indeno[1,2-b]quinolin-8-one

Crystal data

C26H14FNO	F(000) = 388
Mr = 375.38	Dx = 1.373 Mg m^−3
Monoclinic, P21	Melting point: 573 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 10.971 (4) Å	Cell parameters from 1015 reflections
b = 6.274 (2) Å	θ = 2.7–21.4°
c = 13.540 (4) Å	µ = 0.09 mm^−1
β = 103.115 (5)°	T = 298 K
V = 907.7 (5) Å^3	Block, yellow
Z = 2	0.50 × 0.23 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1751 independent reflections
Radiation source: fine-focus sealed tube	1130 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.956, Tmax = 0.989	k = −6→7
4768 measured reflections	l = −12→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.039P)^2] where P = (Fo^2 + 2Fc^2)/3
1751 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.15 e Å^−3
1 restraint	Δρmin = −0.12 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.

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
F1	0.3839 (2)	0.7223 (5)	0.30521 (16)	0.0961 (10)
N1	0.1713 (3)	0.7988 (5)	0.8671 (2)	0.0462 (8)
O1	0.1005 (2)	1.1449 (4)	0.54655 (19)	0.0646 (8)
C1	0.1334 (3)	0.9332 (6)	0.7916 (3)	0.0432 (9)
C2	0.0542 (3)	1.1217 (6)	0.7952 (2)	0.0433 (9)
C3	0.0012 (3)	1.2001 (7)	0.8706 (3)	0.0538 (10)
H3	0.0123	1.1312	0.9328	0.065*
C4	−0.0692 (3)	1.3850 (7)	0.8510 (3)	0.0582 (11)
H4	−0.1062	1.4407	0.9008	0.070*
C5	−0.0855 (4)	1.4881 (6)	0.7589 (3)	0.0610 (11)
H5	−0.1322	1.6131	0.7480	0.073*
C6	−0.0336 (3)	1.4087 (7)	0.6825 (3)	0.0563 (10)
H6	−0.0450	1.4776	0.6202	0.068*
C7	0.0359 (3)	1.2238 (6)	0.7017 (3)	0.0471 (10)
C8	0.1010 (3)	1.1024 (6)	0.6339 (3)	0.0506 (10)
C9	0.1646 (3)	0.9217 (6)	0.6963 (2)	0.0428 (9)
C10	0.2394 (3)	0.7608 (6)	0.6754 (3)	0.0421 (9)
C11	0.2795 (3)	0.6083 (6)	0.7539 (3)	0.0437 (9)
C12	0.3549 (3)	0.4273 (7)	0.7417 (3)	0.0533 (10)
H12	0.3809	0.4108	0.6814	0.064*
C13	0.3886 (3)	0.2812 (7)	0.8153 (3)	0.0587 (11)
H13	0.4350	0.1635	0.8037	0.070*
C14	0.3556 (3)	0.3014 (6)	0.9102 (3)	0.0494 (10)
C15	0.3908 (3)	0.1507 (7)	0.9868 (3)	0.0643 (12)
H15	0.4339	0.0293	0.9749	0.077*
C16	0.3630 (4)	0.1784 (8)	1.0790 (3)	0.0725 (13)
H16	0.3875	0.0766	1.1296	0.087*
C17	0.2978 (4)	0.3590 (8)	1.0977 (3)	0.0693 (13)
H17	0.2800	0.3779	1.1611	0.083*
C18	0.2599 (3)	0.5088 (7)	1.0238 (3)	0.0565 (11)
H18	0.2167	0.6291	1.0370	0.068*
C19	0.2861 (3)	0.4808 (6)	0.9284 (3)	0.0442 (9)
C20	0.2448 (3)	0.6330 (6)	0.8480 (3)	0.0448 (9)
C21	0.2774 (3)	0.7476 (6)	0.5768 (3)	0.0445 (9)
C22	0.2390 (3)	0.5834 (7)	0.5093 (3)	0.0533 (11)
H22	0.1878	0.4771	0.5256	0.064*
C23	0.2748 (3)	0.5734 (7)	0.4179 (3)	0.0603 (12)
H23	0.2485	0.4622	0.3727	0.072*
C24	0.3497 (4)	0.7311 (8)	0.3962 (3)	0.0608 (12)
C25	0.3895 (4)	0.8958 (8)	0.4588 (3)	0.0691 (13)
H25	0.4399	1.0014	0.4409	0.083*
C26	0.3536 (4)	0.9046 (7)	0.5504 (3)	0.0658 (12)
H26	0.3808	1.0169	0.5948	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0925 (17)	0.141 (3)	0.0671 (15)	−0.008 (2)	0.0434 (14)	−0.0139 (18)
N1	0.0486 (19)	0.0435 (19)	0.0482 (19)	−0.0013 (16)	0.0148 (15)	0.0007 (17)
O1	0.0851 (19)	0.0606 (19)	0.0505 (16)	−0.0033 (16)	0.0205 (14)	−0.0004 (16)
C1	0.047 (2)	0.037 (2)	0.047 (2)	−0.0051 (19)	0.0129 (19)	−0.002 (2)
C2	0.044 (2)	0.041 (2)	0.047 (2)	−0.0035 (19)	0.0131 (17)	−0.003 (2)
C3	0.053 (2)	0.058 (3)	0.053 (2)	0.006 (2)	0.0178 (19)	0.000 (2)
C4	0.055 (3)	0.056 (3)	0.066 (3)	0.004 (2)	0.020 (2)	−0.010 (3)
C5	0.061 (3)	0.048 (3)	0.073 (3)	0.008 (2)	0.013 (2)	0.004 (2)
C6	0.056 (3)	0.051 (3)	0.061 (3)	−0.006 (2)	0.013 (2)	−0.001 (2)
C7	0.047 (2)	0.045 (3)	0.049 (2)	−0.006 (2)	0.0098 (18)	−0.005 (2)
C8	0.058 (2)	0.048 (3)	0.047 (2)	−0.014 (2)	0.016 (2)	−0.003 (2)
C9	0.044 (2)	0.041 (2)	0.045 (2)	−0.0083 (19)	0.0152 (18)	−0.002 (2)
C10	0.040 (2)	0.039 (2)	0.049 (2)	−0.005 (2)	0.0130 (18)	−0.005 (2)
C11	0.037 (2)	0.041 (2)	0.054 (2)	−0.004 (2)	0.0125 (17)	−0.007 (2)
C12	0.044 (2)	0.055 (3)	0.061 (3)	−0.002 (2)	0.0118 (19)	−0.004 (2)
C13	0.051 (3)	0.051 (3)	0.072 (3)	−0.001 (2)	0.011 (2)	−0.011 (3)
C14	0.035 (2)	0.053 (3)	0.057 (3)	−0.005 (2)	0.0049 (18)	−0.008 (2)
C15	0.054 (3)	0.057 (3)	0.076 (3)	0.002 (2)	0.003 (2)	0.001 (3)
C16	0.071 (3)	0.063 (3)	0.077 (3)	0.007 (3)	0.005 (2)	0.019 (3)
C17	0.074 (3)	0.075 (4)	0.061 (3)	0.003 (3)	0.018 (2)	0.015 (3)
C18	0.063 (3)	0.053 (3)	0.055 (2)	0.007 (2)	0.018 (2)	0.008 (2)
C19	0.037 (2)	0.042 (2)	0.053 (2)	−0.0025 (19)	0.0085 (18)	0.002 (2)
C20	0.037 (2)	0.042 (2)	0.056 (2)	−0.004 (2)	0.0129 (18)	−0.006 (2)
C21	0.045 (2)	0.044 (2)	0.046 (2)	−0.003 (2)	0.0144 (18)	−0.005 (2)
C22	0.054 (2)	0.057 (3)	0.052 (2)	−0.005 (2)	0.0188 (19)	−0.006 (2)
C23	0.059 (3)	0.066 (3)	0.056 (3)	0.002 (3)	0.014 (2)	−0.012 (2)
C24	0.056 (3)	0.082 (3)	0.052 (3)	0.001 (3)	0.028 (2)	−0.005 (3)
C25	0.068 (3)	0.075 (3)	0.072 (3)	−0.018 (3)	0.034 (2)	−0.008 (3)
C26	0.070 (3)	0.065 (3)	0.070 (3)	−0.019 (3)	0.032 (2)	−0.008 (3)

Geometric parameters (Å, º)

F1—C24	1.368 (4)	C12—H12	0.93
N1—C1	1.317 (4)	C13—C14	1.418 (5)
N1—C20	1.376 (4)	C13—H13	0.93
O1—C8	1.211 (4)	C14—C15	1.392 (5)
C1—C9	1.409 (4)	C14—C19	1.412 (5)
C1—C2	1.476 (5)	C15—C16	1.362 (5)
C2—C3	1.375 (4)	C15—H15	0.93
C2—C7	1.392 (4)	C16—C17	1.393 (5)
C3—C4	1.386 (5)	C16—H16	0.93
C3—H3	0.93	C17—C18	1.367 (5)
C4—C5	1.380 (5)	C17—H17	0.93
C4—H4	0.93	C18—C19	1.397 (4)
C5—C6	1.382 (5)	C18—H18	0.93
C5—H5	0.93	C19—C20	1.441 (5)
C6—C7	1.380 (5)	C21—C22	1.378 (5)
C6—H6	0.93	C21—C26	1.390 (5)
C7—C8	1.493 (4)	C22—C23	1.382 (4)
C8—C9	1.490 (5)	C22—H22	0.93
C9—C10	1.370 (5)	C23—C24	1.361 (5)
C10—C11	1.424 (5)	C23—H23	0.93
C10—C21	1.489 (4)	C24—C25	1.344 (6)
C11—C20	1.419 (4)	C25—C26	1.385 (5)
C11—C12	1.437 (5)	C25—H25	0.93
C12—C13	1.343 (5)	C26—H26	0.93
C1—N1—C20	115.7 (3)	C15—C14—C19	118.8 (3)
N1—C1—C9	125.3 (3)	C15—C14—C13	122.0 (4)
N1—C1—C2	124.9 (3)	C19—C14—C13	119.2 (4)
C9—C1—C2	109.8 (3)	C16—C15—C14	120.9 (4)
C3—C2—C7	120.9 (3)	C16—C15—H15	119.5
C3—C2—C1	131.5 (3)	C14—C15—H15	119.5
C7—C2—C1	107.6 (3)	C15—C16—C17	120.1 (4)
C2—C3—C4	117.9 (4)	C15—C16—H16	120.0
C2—C3—H3	121.0	C17—C16—H16	120.0
C4—C3—H3	121.0	C18—C17—C16	120.7 (4)
C5—C4—C3	121.2 (3)	C18—C17—H17	119.7
C5—C4—H4	119.4	C16—C17—H17	119.7
C3—C4—H4	119.4	C17—C18—C19	119.9 (4)
C4—C5—C6	121.1 (4)	C17—C18—H18	120.1
C4—C5—H5	119.4	C19—C18—H18	120.1
C6—C5—H5	119.4	C18—C19—C14	119.6 (4)
C7—C6—C5	117.7 (4)	C18—C19—C20	121.3 (3)
C7—C6—H6	121.1	C14—C19—C20	119.1 (3)
C5—C6—H6	121.1	N1—C20—C11	122.6 (3)
C6—C7—C2	121.2 (3)	N1—C20—C19	117.2 (3)
C6—C7—C8	129.3 (4)	C11—C20—C19	120.2 (3)
C2—C7—C8	109.5 (3)	C22—C21—C26	118.1 (3)
O1—C8—C9	128.3 (3)	C22—C21—C10	122.0 (3)
O1—C8—C7	126.3 (4)	C26—C21—C10	119.9 (3)
C9—C8—C7	105.5 (3)	C21—C22—C23	121.4 (4)
C10—C9—C1	120.5 (3)	C21—C22—H22	119.3
C10—C9—C8	132.0 (3)	C23—C22—H22	119.3
C1—C9—C8	107.5 (3)	C24—C23—C22	117.9 (4)
C9—C10—C11	116.0 (3)	C24—C23—H23	121.0
C9—C10—C21	121.9 (3)	C22—C23—H23	121.0
C11—C10—C21	122.0 (3)	C25—C24—C23	123.2 (3)
C20—C11—C10	119.8 (3)	C25—C24—F1	118.9 (4)
C20—C11—C12	117.9 (4)	C23—C24—F1	117.9 (4)
C10—C11—C12	122.3 (3)	C24—C25—C26	118.5 (4)
C13—C12—C11	121.5 (3)	C24—C25—H25	120.7
C13—C12—H12	119.2	C26—C25—H25	120.7
C11—C12—H12	119.2	C25—C26—C21	120.7 (4)
C12—C13—C14	121.9 (4)	C25—C26—H26	119.6
C12—C13—H13	119.1	C21—C26—H26	119.6
C14—C13—H13	119.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1^i	0.93	2.44	3.365 (5)	173
C22—H22···O1^ii	0.93	2.34	3.237 (5)	163
C15—H15···Cg3^iii	0.93	2.88	3.685 (4)	146

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) x, y−1, z; (iii) −x+1, y−1/2, −z+2.