4-(4-Fluoro-benzo-yl)-3-phenyl-3,4-di-hydro-naphthalen-1(2H)-one.

In the title compound, C23H17FO2, the cyclo-hexenone ring has an envelope conformation, the flap atom being the C atom to which the phenyl ring is attached. The 4-fluoro-benzoyl ring and the phenyl ring are inclined to one another by 28.77 (7)°, and by 52.00 (7) and 44.77 (7) °, respectively, to the aromatic ring fused to the cyclo-hexenone ring. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (100).

Related literature

For the domino reaction as an important tool in the construction of structurally complicated mol­ecules, see: Zhao et al. (2012 ▶). For Pd-catalysed cascade reactions, see: Wang & Hu (2011 ▶); Yu & Hu (2012 ▶). For the use of condensed polycyclic compounds as synthetic building blocks, pharmacophores and electroluminescent materials, see: Rixson et al. (2012 ▶). For cross-coupling reactions of aryl halides with olefins and diynes, see: Hu et al. (2010 ▶, 2009 ▶).

Experimental

Crystal data

C23H17FO2

M = 344.37

Monoclinic,

a = 8.0063 (6) Å

b = 10.6688 (8) Å

c = 20.3796 (15) Å

β = 97.458 (1)°

V = 1726.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.35 × 0.32 × 0.29 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.969, T max = 0.974

14632 measured reflections

3987 independent reflections

3176 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.117

S = 1.03

3987 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008829/rk2398sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008829/rk2398Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008829/rk2398Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H17FO2	F(000) = 720
Mr = 344.37	Dx = 1.325 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2731 reflections
a = 8.0063 (6) Å	θ = 2.1–23.6°
b = 10.6688 (8) Å	µ = 0.09 mm−1
c = 20.3796 (15) Å	T = 295 K
β = 97.458 (1)°	Block, colourless
V = 1726.1 (2) Å3	0.35 × 0.32 × 0.29 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3987 independent reflections
Radiation source: sealed tube	3176 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ– and ω–scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.969, Tmax = 0.974	k = −13→13
14632 measured reflections	l = −26→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.05P)2 + 0.44P] where P = (Fo2 + 2Fc2)/3
3987 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq
C1	1.2122 (2)	0.13272 (15)	0.42049 (7)	0.0558 (4)
H1	1.1940	0.0940	0.4598	0.067*
C2	1.3639 (2)	0.18874 (18)	0.41545 (8)	0.0638 (5)
H2	1.4479	0.1890	0.4515	0.077*
C3	1.39238 (19)	0.24486 (16)	0.35687 (8)	0.0590 (4)
H3	1.4957	0.2826	0.3536	0.071*
C4	1.26809 (17)	0.24528 (14)	0.30301 (7)	0.0474 (3)
H4	1.2892	0.2820	0.2635	0.057*
C5	1.11203 (16)	0.19136 (12)	0.30728 (6)	0.0380 (3)
C6	1.08446 (17)	0.13349 (12)	0.36657 (6)	0.0429 (3)
C7	0.92053 (19)	0.07364 (12)	0.37339 (6)	0.0447 (3)
C8	0.78176 (17)	0.08569 (13)	0.31679 (7)	0.0450 (3)
H8A	0.6749	0.0903	0.3343	0.054*
H8B	0.7800	0.0109	0.2896	0.054*
C9	0.79881 (15)	0.19977 (12)	0.27346 (6)	0.0379 (3)
H9	0.7963	0.2734	0.3021	0.045*
C10	0.97521 (15)	0.19869 (11)	0.24892 (6)	0.0346 (3)
H10	0.9888	0.2775	0.2255	0.041*
C11	0.98542 (16)	0.09084 (11)	0.20047 (6)	0.0362 (3)
C12	0.92979 (15)	0.11179 (11)	0.12871 (6)	0.0363 (3)
C13	0.93535 (19)	0.22788 (13)	0.09884 (7)	0.0466 (3)
H13	0.9760	0.2966	0.1241	0.056*
C14	0.8814 (2)	0.24341 (16)	0.03199 (7)	0.0573 (4)
H14	0.8879	0.3210	0.0117	0.069*
C15	0.8189 (2)	0.14184 (17)	−0.00295 (7)	0.0574 (4)
C16	0.8094 (2)	0.02478 (18)	0.02434 (8)	0.0660 (5)
H16	0.7648	−0.0426	−0.0011	0.079*
C17	0.8681 (2)	0.00996 (14)	0.09066 (7)	0.0522 (4)
H17	0.8662	−0.0689	0.1100	0.063*
C18	0.65496 (16)	0.21523 (12)	0.21773 (6)	0.0400 (3)
C19	0.62893 (18)	0.33103 (14)	0.18694 (8)	0.0496 (3)
H19	0.6977	0.3983	0.2016	0.060*
C20	0.5021 (2)	0.34751 (17)	0.13476 (8)	0.0608 (4)
H20	0.4877	0.4252	0.1141	0.073*
C21	0.3973 (2)	0.24981 (19)	0.11325 (8)	0.0655 (5)
H21	0.3120	0.2612	0.0782	0.079*
C22	0.4193 (2)	0.13585 (18)	0.14369 (9)	0.0648 (5)
H22	0.3475	0.0698	0.1297	0.078*
C23	0.54788 (19)	0.11786 (15)	0.19539 (8)	0.0524 (4)
H23	0.5624	0.0395	0.2153	0.063*
F1	0.76491 (16)	0.15640 (12)	−0.06863 (5)	0.0895 (4)
O1	0.89843 (17)	0.01466 (11)	0.42256 (5)	0.0676 (3)
O2	1.02932 (15)	−0.01260 (9)	0.22076 (5)	0.0544 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0642 (10)	0.0602 (9)	0.0388 (8)	0.0110 (7)	−0.0090 (7)	−0.0028 (6)
C2	0.0542 (9)	0.0783 (11)	0.0523 (9)	0.0133 (8)	−0.0180 (7)	−0.0134 (8)
C3	0.0405 (7)	0.0705 (10)	0.0628 (10)	0.0041 (7)	−0.0052 (7)	−0.0164 (8)
C4	0.0418 (7)	0.0519 (8)	0.0474 (8)	0.0032 (6)	0.0013 (6)	−0.0090 (6)
C5	0.0411 (6)	0.0355 (6)	0.0356 (6)	0.0058 (5)	−0.0025 (5)	−0.0072 (5)
C6	0.0510 (8)	0.0405 (7)	0.0349 (6)	0.0072 (6)	−0.0033 (5)	−0.0044 (5)
C7	0.0633 (9)	0.0361 (7)	0.0339 (7)	0.0038 (6)	0.0028 (6)	−0.0010 (5)
C8	0.0474 (7)	0.0448 (7)	0.0424 (7)	−0.0022 (6)	0.0048 (6)	0.0037 (6)
C9	0.0398 (6)	0.0359 (6)	0.0370 (6)	0.0018 (5)	0.0014 (5)	−0.0020 (5)
C10	0.0396 (6)	0.0301 (6)	0.0327 (6)	0.0003 (5)	−0.0004 (5)	−0.0008 (4)
C11	0.0406 (6)	0.0316 (6)	0.0353 (6)	−0.0001 (5)	0.0007 (5)	−0.0007 (5)
C12	0.0383 (6)	0.0373 (6)	0.0329 (6)	0.0014 (5)	0.0028 (5)	−0.0008 (5)
C13	0.0598 (8)	0.0407 (7)	0.0382 (7)	−0.0004 (6)	0.0020 (6)	0.0027 (5)
C14	0.0731 (10)	0.0558 (9)	0.0422 (8)	0.0100 (8)	0.0050 (7)	0.0127 (7)
C15	0.0601 (9)	0.0781 (11)	0.0311 (7)	0.0101 (8)	−0.0048 (6)	0.0025 (7)
C16	0.0846 (12)	0.0691 (11)	0.0407 (8)	−0.0139 (9)	−0.0061 (8)	−0.0110 (7)
C17	0.0715 (10)	0.0449 (8)	0.0387 (7)	−0.0079 (7)	0.0013 (7)	−0.0022 (6)
C18	0.0362 (6)	0.0441 (7)	0.0395 (7)	0.0054 (5)	0.0036 (5)	−0.0030 (5)
C19	0.0455 (7)	0.0466 (8)	0.0550 (8)	0.0065 (6)	−0.0002 (6)	0.0026 (6)
C20	0.0554 (9)	0.0670 (10)	0.0586 (10)	0.0192 (8)	0.0014 (7)	0.0122 (8)
C21	0.0489 (9)	0.0930 (13)	0.0505 (9)	0.0118 (9)	−0.0088 (7)	−0.0001 (9)
C22	0.0524 (9)	0.0777 (12)	0.0597 (10)	−0.0067 (8)	−0.0104 (7)	−0.0119 (9)
C23	0.0505 (8)	0.0510 (8)	0.0533 (8)	−0.0019 (6)	−0.0032 (6)	−0.0033 (7)
F1	0.1108 (9)	0.1147 (9)	0.0360 (5)	0.0106 (7)	−0.0174 (5)	0.0072 (5)
O1	0.0949 (9)	0.0638 (7)	0.0418 (6)	−0.0137 (6)	0.0003 (6)	0.0132 (5)
O2	0.0832 (8)	0.0338 (5)	0.0426 (5)	0.0118 (5)	−0.0052 (5)	0.0003 (4)

C1—C2	1.369 (2)	C11—C12	1.4892 (17)
C1—C6	1.4009 (19)	C12—C13	1.3834 (18)
C1—H1	0.9300	C12—C17	1.3880 (18)
C2—C3	1.381 (3)	C13—C14	1.3846 (19)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.3825 (19)	C14—C15	1.356 (2)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.3885 (19)	C15—F1	1.3610 (17)
C4—H4	0.9300	C15—C16	1.373 (2)
C5—C6	1.3997 (19)	C16—C17	1.381 (2)
C5—C10	1.5108 (16)	C16—H16	0.9300
C6—C7	1.482 (2)	C17—H17	0.9300
C7—O1	1.2154 (17)	C18—C23	1.3857 (19)
C7—C8	1.4996 (19)	C18—C19	1.3891 (19)
C8—C9	1.5203 (18)	C19—C20	1.383 (2)
C8—H8A	0.9700	C19—H19	0.9300
C8—H8B	0.9700	C20—C21	1.374 (3)
C9—C18	1.5180 (17)	C20—H20	0.9300
C9—C10	1.5583 (17)	C21—C22	1.366 (3)
C9—H9	0.9800	C21—H21	0.9300
C10—C11	1.5253 (16)	C22—C23	1.388 (2)
C10—H10	0.9800	C22—H22	0.9300
C11—O2	1.2144 (15)	C23—H23	0.9300
C2—C1—C6	120.20 (15)	O2—C11—C12	120.48 (11)
C2—C1—H1	119.9	O2—C11—C10	120.17 (11)
C6—C1—H1	119.9	C12—C11—C10	119.22 (10)
C1—C2—C3	120.11 (14)	C13—C12—C17	118.97 (12)
C1—C2—H2	119.9	C13—C12—C11	122.95 (11)
C3—C2—H2	119.9	C17—C12—C11	118.07 (11)
C2—C3—C4	120.35 (15)	C12—C13—C14	121.09 (14)
C2—C3—H3	119.8	C12—C13—H13	119.5
C4—C3—H3	119.8	C14—C13—H13	119.5
C3—C4—C5	120.65 (14)	C15—C14—C13	117.89 (15)
C3—C4—H4	119.7	C15—C14—H14	121.1
C5—C4—H4	119.7	C13—C14—H14	121.1
C4—C5—C6	118.74 (12)	C14—C15—F1	118.27 (15)
C4—C5—C10	119.71 (12)	C14—C15—C16	123.37 (14)
C6—C5—C10	121.53 (12)	F1—C15—C16	118.35 (15)
C5—C6—C1	119.92 (13)	C15—C16—C17	118.08 (15)
C5—C6—C7	120.78 (11)	C15—C16—H16	121.0
C1—C6—C7	119.29 (13)	C17—C16—H16	121.0
O1—C7—C6	121.72 (13)	C16—C17—C12	120.56 (14)
O1—C7—C8	120.39 (14)	C16—C17—H17	119.7
C6—C7—C8	117.88 (11)	C12—C17—H17	119.7
C7—C8—C9	113.70 (11)	C23—C18—C19	117.92 (13)
C7—C8—H8A	108.8	C23—C18—C9	122.78 (12)
C9—C8—H8A	108.8	C19—C18—C9	119.30 (12)
C7—C8—H8B	108.8	C20—C19—C18	120.83 (15)
C9—C8—H8B	108.8	C20—C19—H19	119.6
H8A—C8—H8B	107.7	C18—C19—H19	119.6
C18—C9—C8	113.89 (11)	C21—C20—C19	120.40 (16)
C18—C9—C10	113.07 (10)	C21—C20—H20	119.8
C8—C9—C10	109.51 (10)	C19—C20—H20	119.8
C18—C9—H9	106.6	C22—C21—C20	119.56 (15)
C8—C9—H9	106.6	C22—C21—H21	120.2
C10—C9—H9	106.6	C20—C21—H21	120.2
C5—C10—C11	112.10 (10)	C21—C22—C23	120.46 (16)
C5—C10—C9	110.03 (10)	C21—C22—H22	119.8
C11—C10—C9	109.89 (10)	C23—C22—H22	119.8
C5—C10—H10	108.2	C18—C23—C22	120.82 (15)
C11—C10—H10	108.2	C18—C23—H23	119.6
C9—C10—H10	108.2	C22—C23—H23	119.6
C6—C1—C2—C3	−0.8 (2)	C5—C10—C11—C12	−148.71 (11)
C1—C2—C3—C4	0.2 (3)	C9—C10—C11—C12	88.60 (13)
C2—C3—C4—C5	1.1 (2)	O2—C11—C12—C13	−156.49 (14)
C3—C4—C5—C6	−1.8 (2)	C10—C11—C12—C13	27.68 (18)
C3—C4—C5—C10	176.91 (12)	O2—C11—C12—C17	24.2 (2)
C4—C5—C6—C1	1.10 (19)	C10—C11—C12—C17	−151.59 (12)
C10—C5—C6—C1	−177.54 (12)	C17—C12—C13—C14	−0.3 (2)
C4—C5—C6—C7	−179.46 (12)	C11—C12—C13—C14	−179.61 (13)
C10—C5—C6—C7	1.90 (18)	C12—C13—C14—C15	1.7 (2)
C2—C1—C6—C5	0.2 (2)	C13—C14—C15—F1	179.74 (15)
C2—C1—C6—C7	−179.26 (14)	C13—C14—C15—C16	−1.2 (3)
C5—C6—C7—O1	174.25 (13)	C14—C15—C16—C17	−0.5 (3)
C1—C6—C7—O1	−6.3 (2)	F1—C15—C16—C17	178.48 (15)
C5—C6—C7—C8	−4.57 (18)	C15—C16—C17—C12	1.9 (3)
C1—C6—C7—C8	174.87 (13)	C13—C12—C17—C16	−1.5 (2)
O1—C7—C8—C9	156.38 (13)	C11—C12—C17—C16	177.80 (14)
C6—C7—C8—C9	−24.80 (17)	C8—C9—C18—C23	−18.97 (18)
C7—C8—C9—C18	−177.69 (11)	C10—C9—C18—C23	106.89 (15)
C7—C8—C9—C10	54.60 (14)	C8—C9—C18—C19	161.63 (12)
C4—C5—C10—C11	87.24 (14)	C10—C9—C18—C19	−72.51 (15)
C6—C5—C10—C11	−94.14 (14)	C23—C18—C19—C20	−1.3 (2)
C4—C5—C10—C9	−150.15 (12)	C9—C18—C19—C20	178.14 (13)
C6—C5—C10—C9	28.47 (15)	C18—C19—C20—C21	1.2 (2)
C18—C9—C10—C5	176.40 (10)	C19—C20—C21—C22	−0.1 (3)
C8—C9—C10—C5	−55.42 (13)	C20—C21—C22—C23	−0.9 (3)
C18—C9—C10—C11	−59.70 (13)	C19—C18—C23—C22	0.2 (2)
C8—C9—C10—C11	68.48 (13)	C9—C18—C23—C22	−179.17 (14)
C5—C10—C11—O2	35.45 (17)	C21—C22—C23—C18	0.9 (3)
C9—C10—C11—O2	−87.23 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	0.93	2.53	3.425 (2)	161
C10—H10···O2ii	0.98	2.51	3.1427 (15)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	0.93	2.53	3.425 (2)	161
C10—H10⋯O2ii	0.98	2.51	3.1427 (15)	123

Symmetry codes: (i) ; (ii) .