3-(Biphen­yl-4-yl)-1-(4-fluoro­phen­yl)prop-2-en-1-one

Sarojini, B.K.; Yathirajan, H.S.; Sreevidya, T.V.; Narayana, B.; Bolte, M.

doi:10.1107/S1600536807023434

3-(Biphenyl-4-yl)-1-(4-fluorophenyl)prop-2-en-1-one

B. K. Sarojini, H. S. Yathirajan, T. V. Sreevidya, B. Narayana and M. Bolte

The title compound, C₂₁H₁₅FO, crystallizes with two molecules in the asymmetric unit, which differ only in the signs of their torsion angles. Nevertheless, the two molecules are not related by any crystallographic symmetry element. The dihedral angles between the two phenyl rings of the biphenyl unit are 3.0 (2) and 2.1 (2)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023434/pv2013sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023434/pv2013Isup2.hkl Contains datablock I

CCDC reference: 651583

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.006 Å
R factor = 0.053
wR factor = 0.150
Data-to-parameter ratio = 6.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.61
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           25.07
           From the CIF: _reflns_number_total               2748
           Count of symmetry unique reflns         2768
           Completeness (_total/calc)             99.28%
           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
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 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
   3 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

Comment top

Chalcones (1,3-diaryl-2-propen-1-ones), belonging to the flavonoid family is one of the major class of natural products which have been recently subjects of great interest for their interesting pharmacological activities. Chalcones have been reported to possess many useful properties, including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities. Among several organic compounds reported for NLO property, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. We have synthesized a new chalcone.

The title compound, C₂₁H₁₅FO, crystallized with two molecules in the asymmetric unit, which differ only in the sign of their torsion angles. A least-squares fit of all non H atoms of molecule one with the inverted molecule two gives an r.m.s. deviation of 0.022 Å. Nevertheless, the two molecules are not related by any crystallographic symmetry element (Fig. 2). The dihedral angle between the two phenyl rings of the biphenyl unit is 3.0 (2)% and 2.1 (2)°, respectively.

Related literature top

For related structures, see: (2E)-3-(biphenyl-4-yl)-1-phenylprop-2-en-1-one (Fischer et al., 2007e); (2E)-3-(biphenyl-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (Fischer et al., 2007a); (2E)-3-(biphenyl-4-yl)-1-(2,4-dichlorophenyl)prop-2-en-1-one (Fischer et al., 2007b); (2E)-3-(biphenyl-4-yl)-1-(4-chlorophenyl)prop-2-en-1-one (Fischer et al., 2007c); (2E)-3-(biphenyl-4-yl)-1-(4-bromophenyl)prop-2-en-1-one (Fischer et al., 2007d); 3-(biphenyl-4-yl)-2,3-dibromo-1-(2,4-dichlorophenyl)propan-1-one (Yathirajan et al., 2007).

For related literature, see: Carlo et al. (1999); Fichou et al., (1988); Goto et al., (1991); Uchida et al. (1998); Zhao et al. (2000); Sarojini et al. (2006).

Experimental top

A solution of potassium hydroxide (5%, 5 ml) was added slowly with stirring to a mixture of biphenyl aldehyde (1.8 g, 0.01 mol) and 4-fluoroacetophenone (1.38 g, 0.01 mol) in ethanol (15 ml). The mixture was stirred at room temperature for 6 h. The precipitated solid was filtered, washed with cold ethanol, dried and recrystallized from ethanol (yield: 83%; m.p.:405–407 K). Analysis for C₂₁H₁₅FO: Found (Calculated): C: 83.30 (83.42); H: 4.91% (5.00%).

Structure description top

For related literature, see: Carlo et al. (1999); Fichou et al., (1988); Goto et al., (1991); Uchida et al. (1998); Zhao et al. (2000); Sarojini et al. (2006).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
	Fig. 2. Packing diagram of the title compound.

3-(biphenyl)-1-(4-fluorophenyl)prop-2-en-1-one top

Crystal data top

C₂₁H₁₅FO	F(000) = 632
M_r = 302.33	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 11222 reflections
a = 6.0095 (5) Å	θ = 2.4–25.4°
b = 35.278 (3) Å	µ = 0.09 mm⁻¹
c = 7.2352 (6) Å	T = 173 K
β = 90.018 (7)°	Plate, colourless
V = 1533.9 (2) Å³	0.24 × 0.23 × 0.07 mm
Z = 4

Data collection top

STOE IPDS II two-circle- diffractometer	2247 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.078
Graphite monochromator	θ_max = 25.1°, θ_min = 2.3°
ω scans	h = −6→7
11797 measured reflections	k = −41→41
2748 independent reflections	l = −8→7

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.0971P)² + 0.1253P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2748 reflections	Δρ_max = 0.24 e Å⁻³
416 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (5)

Crystal data top

C₂₁H₁₅FO	V = 1533.9 (2) Å³
M_r = 302.33	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 6.0095 (5) Å	µ = 0.09 mm⁻¹
b = 35.278 (3) Å	T = 173 K
c = 7.2352 (6) Å	0.24 × 0.23 × 0.07 mm
β = 90.018 (7)°

Data collection top

STOE IPDS II two-circle- diffractometer	2247 reflections with I > 2σ(I)
11797 measured reflections	R_int = 0.078
2748 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.150	H-atom parameters constrained
S = 1.08	Δρ_max = 0.24 e Å⁻³
2748 reflections	Δρ_min = −0.21 e Å⁻³
416 parameters

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.

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

	x	y	z	U_iso*/U_eq
F1	0.9293 (5)	0.05442 (9)	0.7455 (5)	0.0675 (9)
O1	0.3329 (5)	0.19910 (10)	0.6711 (5)	0.0543 (9)
C1	0.5359 (7)	0.19750 (14)	0.6794 (6)	0.0390 (10)
C2	0.6741 (8)	0.23236 (12)	0.6773 (6)	0.0400 (10)
H2	0.8271	0.2309	0.6453	0.048*
C3	0.5832 (7)	0.26574 (14)	0.7206 (6)	0.0391 (10)
H3	0.4313	0.2653	0.7570	0.047*
C11	0.6470 (7)	0.16017 (13)	0.6914 (6)	0.0356 (9)
C12	0.8594 (7)	0.15582 (14)	0.7682 (6)	0.0418 (11)
H12	0.9401	0.1775	0.8078	0.050*
C13	0.9530 (7)	0.12006 (15)	0.7871 (7)	0.0455 (11)
H13	1.0967	0.1171	0.8399	0.055*
C14	0.8367 (8)	0.08951 (14)	0.7293 (7)	0.0443 (11)
C15	0.6264 (7)	0.09220 (13)	0.6512 (7)	0.0437 (11)
H15	0.5489	0.0702	0.6110	0.052*
C16	0.5339 (7)	0.12755 (13)	0.6339 (6)	0.0398 (10)
H16	0.3895	0.1300	0.5817	0.048*
C21	0.6921 (7)	0.30301 (12)	0.7181 (6)	0.0333 (9)
C22	0.5779 (7)	0.33406 (12)	0.7906 (6)	0.0357 (10)
H22	0.4349	0.3304	0.8437	0.043*
C23	0.6694 (7)	0.37021 (12)	0.7867 (6)	0.0332 (9)
H23	0.5869	0.3908	0.8362	0.040*
C24	0.8798 (7)	0.37701 (12)	0.7115 (6)	0.0321 (9)
C25	0.9948 (7)	0.34561 (12)	0.6367 (6)	0.0360 (9)
H25	1.1370	0.3492	0.5821	0.043*
C26	0.9029 (7)	0.30978 (12)	0.6419 (6)	0.0356 (10)
H26	0.9848	0.2891	0.5924	0.043*
C31	0.9783 (7)	0.41586 (11)	0.7093 (5)	0.0313 (9)
C32	0.8697 (7)	0.44664 (13)	0.7904 (6)	0.0364 (10)
H32	0.7318	0.4425	0.8514	0.044*
C33	0.9562 (8)	0.48266 (13)	0.7848 (7)	0.0413 (10)
H33	0.8753	0.5031	0.8381	0.050*
C34	1.1616 (8)	0.48961 (13)	0.7018 (6)	0.0412 (10)
H34	1.2225	0.5145	0.6994	0.049*
C35	1.2753 (7)	0.45932 (12)	0.6224 (6)	0.0384 (10)
H35	1.4162	0.4634	0.5665	0.046*
C36	1.1845 (7)	0.42326 (12)	0.6245 (6)	0.0361 (9)
H36	1.2632	0.4031	0.5674	0.043*
F1A	0.5605 (5)	0.55587 (8)	0.8197 (5)	0.0630 (9)
O1A	1.1685 (5)	0.69972 (10)	0.7490 (5)	0.0533 (9)
C1A	0.9635 (7)	0.69835 (14)	0.7567 (6)	0.0386 (10)
C2A	0.8260 (8)	0.73304 (12)	0.7556 (6)	0.0396 (10)
H2A	0.6734	0.7317	0.7222	0.047*
C3A	0.9166 (7)	0.76640 (13)	0.8017 (6)	0.0378 (10)
H3A	1.0678	0.7659	0.8398	0.045*
C11A	0.8495 (7)	0.66086 (13)	0.7687 (6)	0.0371 (10)
C12A	0.6396 (7)	0.65722 (13)	0.8457 (6)	0.0378 (10)
H12A	0.5615	0.6792	0.8856	0.045*
C13A	0.5420 (7)	0.62161 (14)	0.8650 (7)	0.0426 (10)
H13A	0.3991	0.6190	0.9197	0.051*
C14A	0.6560 (8)	0.59074 (13)	0.8039 (7)	0.0428 (11)
C15A	0.8655 (8)	0.59300 (14)	0.7244 (7)	0.0440 (11)
H15A	0.9404	0.5709	0.6822	0.053*
C16A	0.9612 (7)	0.62829 (13)	0.7086 (6)	0.0390 (10)
H16A	1.1054	0.6306	0.6561	0.047*
C21A	0.8078 (7)	0.80367 (12)	0.7998 (6)	0.0327 (9)
C22A	0.9213 (7)	0.83501 (11)	0.8713 (6)	0.0344 (9)
H22A	1.0656	0.8315	0.9223	0.041*
C23A	0.8293 (7)	0.87083 (12)	0.8697 (6)	0.0342 (9)
H23A	0.9108	0.8913	0.9216	0.041*
C24A	0.6190 (7)	0.87784 (11)	0.7938 (6)	0.0306 (9)
C25A	0.5064 (7)	0.84613 (12)	0.7194 (6)	0.0319 (9)
H25A	0.3640	0.8497	0.6651	0.038*
C26A	0.5966 (8)	0.81006 (13)	0.7231 (6)	0.0369 (10)
H26A	0.5147	0.7894	0.6733	0.044*
C31A	0.5228 (7)	0.91661 (12)	0.7907 (6)	0.0319 (9)
C32A	0.6346 (7)	0.94764 (12)	0.8707 (6)	0.0370 (9)
H32A	0.7740	0.9435	0.9293	0.044*
C33A	0.5476 (7)	0.98384 (13)	0.8663 (7)	0.0412 (10)
H33A	0.6282	1.0042	0.9206	0.049*
C34A	0.3416 (7)	0.99082 (13)	0.7827 (6)	0.0379 (10)
H34A	0.2821	1.0158	0.7787	0.045*
C35A	0.2254 (7)	0.96054 (13)	0.7054 (6)	0.0387 (10)
H35A	0.0855	0.9648	0.6478	0.046*
C36A	0.3132 (7)	0.92418 (12)	0.7122 (6)	0.0337 (9)
H36A	0.2293	0.9038	0.6624	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0575 (19)	0.0508 (18)	0.094 (3)	0.0133 (15)	0.0044 (16)	0.0068 (16)
O1	0.0339 (18)	0.0486 (19)	0.081 (2)	−0.0034 (15)	−0.0018 (15)	0.0000 (18)
C1	0.032 (2)	0.046 (2)	0.040 (2)	−0.005 (2)	0.0027 (17)	−0.002 (2)
C2	0.039 (2)	0.040 (3)	0.041 (2)	−0.0042 (19)	0.0020 (18)	−0.0048 (19)
C3	0.036 (2)	0.046 (3)	0.035 (2)	−0.009 (2)	0.0007 (17)	−0.0007 (19)
C11	0.036 (2)	0.040 (2)	0.031 (2)	−0.0038 (19)	0.0032 (16)	0.0010 (18)
C12	0.033 (2)	0.053 (3)	0.039 (3)	−0.008 (2)	0.0027 (18)	−0.001 (2)
C13	0.031 (2)	0.061 (3)	0.044 (3)	0.003 (2)	0.0008 (19)	0.007 (2)
C14	0.041 (3)	0.039 (3)	0.052 (3)	0.004 (2)	0.013 (2)	0.006 (2)
C15	0.038 (2)	0.043 (3)	0.050 (3)	−0.005 (2)	0.0015 (19)	−0.001 (2)
C16	0.034 (2)	0.049 (3)	0.037 (2)	−0.007 (2)	0.0054 (18)	−0.002 (2)
C21	0.032 (2)	0.040 (2)	0.028 (2)	−0.0006 (18)	0.0016 (16)	−0.0004 (17)
C22	0.029 (2)	0.042 (2)	0.036 (3)	0.0038 (18)	−0.0011 (17)	−0.0003 (18)
C23	0.027 (2)	0.040 (2)	0.032 (2)	0.0038 (18)	−0.0002 (16)	−0.0028 (17)
C24	0.028 (2)	0.043 (2)	0.025 (2)	0.0016 (17)	−0.0009 (15)	0.0015 (16)
C25	0.031 (2)	0.042 (2)	0.035 (2)	0.0033 (18)	0.0082 (17)	0.0022 (18)
C26	0.034 (2)	0.033 (2)	0.040 (3)	0.0007 (17)	0.0046 (17)	−0.0046 (17)
C31	0.034 (2)	0.038 (2)	0.023 (2)	0.0014 (17)	−0.0002 (16)	0.0010 (15)
C32	0.030 (2)	0.042 (2)	0.037 (2)	0.0003 (18)	0.0030 (17)	0.0005 (19)
C33	0.046 (3)	0.033 (2)	0.044 (3)	0.0047 (19)	0.0063 (19)	−0.0032 (18)
C34	0.041 (2)	0.041 (2)	0.042 (3)	−0.003 (2)	−0.0002 (19)	0.0019 (19)
C35	0.034 (2)	0.044 (2)	0.036 (2)	−0.0019 (19)	0.0057 (17)	0.0011 (18)
C36	0.032 (2)	0.042 (2)	0.034 (2)	0.0036 (18)	0.0029 (17)	−0.0014 (18)
F1A	0.0545 (18)	0.0416 (16)	0.093 (2)	−0.0106 (13)	0.0007 (16)	0.0079 (15)
O1A	0.0342 (18)	0.0443 (19)	0.081 (3)	0.0014 (15)	0.0039 (15)	0.0009 (17)
C1A	0.034 (2)	0.044 (2)	0.037 (2)	0.008 (2)	0.0025 (16)	0.002 (2)
C2A	0.037 (2)	0.038 (2)	0.044 (3)	0.0031 (19)	−0.0032 (18)	0.0017 (19)
C3A	0.037 (2)	0.045 (2)	0.032 (2)	0.004 (2)	0.0060 (16)	0.0011 (19)
C11A	0.033 (2)	0.039 (2)	0.039 (3)	0.0030 (18)	−0.0036 (18)	0.0025 (19)
C12A	0.034 (2)	0.042 (2)	0.038 (2)	0.0061 (19)	0.0063 (17)	0.0002 (18)
C13A	0.034 (2)	0.050 (3)	0.044 (3)	−0.002 (2)	−0.0022 (18)	0.004 (2)
C14A	0.039 (2)	0.041 (3)	0.048 (3)	−0.004 (2)	0.000 (2)	0.005 (2)
C15A	0.043 (2)	0.043 (3)	0.046 (3)	0.007 (2)	−0.003 (2)	0.001 (2)
C16A	0.034 (2)	0.043 (2)	0.040 (2)	0.0044 (19)	0.0020 (17)	−0.0002 (19)
C21A	0.031 (2)	0.038 (2)	0.029 (2)	0.0011 (18)	0.0061 (16)	0.0029 (17)
C22A	0.026 (2)	0.042 (2)	0.035 (2)	0.0005 (18)	−0.0014 (16)	0.0031 (18)
C23A	0.035 (2)	0.039 (2)	0.029 (2)	−0.0048 (18)	0.0014 (16)	0.0000 (17)
C24A	0.029 (2)	0.037 (2)	0.026 (2)	−0.0008 (16)	0.0048 (16)	0.0012 (16)
C25A	0.026 (2)	0.038 (2)	0.031 (2)	−0.0011 (17)	−0.0020 (16)	−0.0018 (17)
C26A	0.039 (2)	0.038 (2)	0.034 (2)	−0.0029 (19)	−0.0025 (17)	−0.0026 (17)
C31A	0.032 (2)	0.037 (2)	0.027 (2)	−0.0029 (17)	0.0053 (16)	0.0024 (16)
C32A	0.034 (2)	0.042 (2)	0.035 (2)	0.0000 (19)	−0.0040 (17)	0.0011 (18)
C33A	0.043 (3)	0.039 (2)	0.042 (3)	−0.005 (2)	0.0036 (19)	−0.0006 (19)
C34A	0.040 (2)	0.036 (2)	0.037 (2)	0.0058 (19)	0.0068 (18)	0.0000 (18)
C35A	0.031 (2)	0.047 (3)	0.038 (2)	0.0063 (19)	0.0021 (18)	0.0028 (19)
C36A	0.027 (2)	0.040 (2)	0.034 (2)	−0.0006 (18)	0.0043 (16)	−0.0008 (17)

Geometric parameters (Å, º) top

F1—C14	1.362 (5)	F1A—C14A	1.362 (5)
O1—C1	1.223 (5)	O1A—C1A	1.234 (5)
C1—C11	1.479 (7)	C1A—C2A	1.477 (6)
C1—C2	1.484 (6)	C1A—C11A	1.492 (6)
C2—C3	1.336 (6)	C2A—C3A	1.339 (6)
C2—H2	0.9500	C2A—H2A	0.9500
C3—C21	1.469 (6)	C3A—C21A	1.468 (6)
C3—H3	0.9500	C3A—H3A	0.9500
C11—C16	1.400 (6)	C11A—C12A	1.385 (6)
C11—C12	1.401 (6)	C11A—C16A	1.400 (6)
C12—C13	1.388 (7)	C12A—C13A	1.393 (7)
C12—H12	0.9500	C12A—H12A	0.9500
C13—C14	1.351 (7)	C13A—C14A	1.361 (7)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.387 (7)	C14A—C15A	1.387 (7)
C15—C16	1.371 (7)	C15A—C16A	1.376 (7)
C15—H15	0.9500	C15A—H15A	0.9500
C16—H16	0.9500	C16A—H16A	0.9500
C21—C22	1.395 (6)	C21A—C22A	1.398 (6)
C21—C26	1.402 (6)	C21A—C26A	1.404 (6)
C22—C23	1.389 (6)	C22A—C23A	1.379 (6)
C22—H22	0.9500	C22A—H22A	0.9500
C23—C24	1.397 (6)	C23A—C24A	1.400 (6)
C23—H23	0.9500	C23A—H23A	0.9500
C24—C25	1.413 (6)	C24A—C25A	1.414 (6)
C24—C31	1.493 (6)	C24A—C31A	1.485 (5)
C25—C26	1.380 (6)	C25A—C26A	1.383 (6)
C25—H25	0.9500	C25A—H25A	0.9500
C26—H26	0.9500	C26A—H26A	0.9500
C31—C32	1.396 (6)	C31A—C36A	1.407 (6)
C31—C36	1.408 (6)	C31A—C32A	1.409 (6)
C32—C33	1.374 (6)	C32A—C33A	1.380 (6)
C32—H32	0.9500	C32A—H32A	0.9500
C33—C34	1.394 (7)	C33A—C34A	1.400 (7)
C33—H33	0.9500	C33A—H33A	0.9500
C34—C35	1.393 (6)	C34A—C35A	1.393 (6)
C34—H34	0.9500	C34A—H34A	0.9500
C35—C36	1.384 (6)	C35A—C36A	1.388 (6)
C35—H35	0.9500	C35A—H35A	0.9500
C36—H36	0.9500	C36A—H36A	0.9500

O1—C1—C11	119.6 (4)	O1A—C1A—C2A	121.7 (4)
O1—C1—C2	121.3 (4)	O1A—C1A—C11A	119.7 (4)
C11—C1—C2	119.1 (4)	C2A—C1A—C11A	118.5 (4)
C3—C2—C1	120.0 (4)	C3A—C2A—C1A	120.0 (4)
C3—C2—H2	120.0	C3A—C2A—H2A	120.0
C1—C2—H2	120.0	C1A—C2A—H2A	120.0
C2—C3—C21	127.2 (4)	C2A—C3A—C21A	127.2 (4)
C2—C3—H3	116.4	C2A—C3A—H3A	116.4
C21—C3—H3	116.4	C21A—C3A—H3A	116.4
C16—C11—C12	118.1 (4)	C12A—C11A—C16A	119.0 (4)
C16—C11—C1	119.7 (4)	C12A—C11A—C1A	121.6 (4)
C12—C11—C1	122.2 (4)	C16A—C11A—C1A	119.3 (4)
C13—C12—C11	120.5 (4)	C11A—C12A—C13A	120.5 (4)
C13—C12—H12	119.7	C11A—C12A—H12A	119.8
C11—C12—H12	119.7	C13A—C12A—H12A	119.8
C14—C13—C12	119.0 (4)	C14A—C13A—C12A	118.5 (4)
C14—C13—H13	120.5	C14A—C13A—H13A	120.8
C12—C13—H13	120.5	C12A—C13A—H13A	120.8
C13—C14—F1	119.1 (4)	C13A—C14A—F1A	118.9 (4)
C13—C14—C15	122.9 (4)	C13A—C14A—C15A	123.1 (4)
F1—C14—C15	118.0 (4)	F1A—C14A—C15A	118.0 (4)
C16—C15—C14	118.0 (4)	C16A—C15A—C14A	117.8 (4)
C16—C15—H15	121.0	C16A—C15A—H15A	121.1
C14—C15—H15	121.0	C14A—C15A—H15A	121.1
C15—C16—C11	121.6 (4)	C15A—C16A—C11A	121.1 (4)
C15—C16—H16	119.2	C15A—C16A—H16A	119.5
C11—C16—H16	119.2	C11A—C16A—H16A	119.5
C22—C21—C26	117.3 (4)	C22A—C21A—C26A	117.4 (4)
C22—C21—C3	118.6 (4)	C22A—C21A—C3A	119.2 (4)
C26—C21—C3	124.1 (4)	C26A—C21A—C3A	123.4 (4)
C23—C22—C21	121.2 (4)	C23A—C22A—C21A	121.7 (4)
C23—C22—H22	119.4	C23A—C22A—H22A	119.1
C21—C22—H22	119.4	C21A—C22A—H22A	119.1
C22—C23—C24	121.6 (4)	C22A—C23A—C24A	121.8 (4)
C22—C23—H23	119.2	C22A—C23A—H23A	119.1
C24—C23—H23	119.2	C24A—C23A—H23A	119.1
C23—C24—C25	117.2 (4)	C23A—C24A—C25A	116.2 (4)
C23—C24—C31	121.4 (4)	C23A—C24A—C31A	121.3 (4)
C25—C24—C31	121.4 (4)	C25A—C24A—C31A	122.4 (3)
C26—C25—C24	120.8 (4)	C26A—C25A—C24A	122.2 (4)
C26—C25—H25	119.6	C26A—C25A—H25A	118.9
C24—C25—H25	119.6	C24A—C25A—H25A	118.9
C25—C26—C21	121.9 (4)	C25A—C26A—C21A	120.6 (4)
C25—C26—H26	119.0	C25A—C26A—H26A	119.7
C21—C26—H26	119.0	C21A—C26A—H26A	119.7
C32—C31—C36	116.8 (4)	C36A—C31A—C32A	116.4 (4)
C32—C31—C24	121.6 (4)	C36A—C31A—C24A	122.0 (4)
C36—C31—C24	121.6 (3)	C32A—C31A—C24A	121.6 (3)
C33—C32—C31	122.0 (4)	C33A—C32A—C31A	121.9 (4)
C33—C32—H32	119.0	C33A—C32A—H32A	119.0
C31—C32—H32	119.0	C31A—C32A—H32A	119.0
C32—C33—C34	120.7 (4)	C32A—C33A—C34A	120.5 (4)
C32—C33—H33	119.7	C32A—C33A—H33A	119.8
C34—C33—H33	119.7	C34A—C33A—H33A	119.8
C35—C34—C33	118.5 (4)	C35A—C34A—C33A	118.8 (4)
C35—C34—H34	120.7	C35A—C34A—H34A	120.6
C33—C34—H34	120.7	C33A—C34A—H34A	120.6
C36—C35—C34	120.5 (4)	C36A—C35A—C34A	120.2 (4)
C36—C35—H35	119.8	C36A—C35A—H35A	119.9
C34—C35—H35	119.8	C34A—C35A—H35A	119.9
C35—C36—C31	121.5 (4)	C35A—C36A—C31A	122.0 (4)
C35—C36—H36	119.3	C35A—C36A—H36A	119.0
C31—C36—H36	119.3	C31A—C36A—H36A	119.0

O1—C1—C2—C3	19.7 (7)	O1A—C1A—C2A—C3A	−20.1 (7)
C11—C1—C2—C3	−160.4 (4)	C11A—C1A—C2A—C3A	159.5 (4)
C1—C2—C3—C21	−177.2 (4)	C1A—C2A—C3A—C21A	177.0 (4)
O1—C1—C11—C16	20.7 (6)	O1A—C1A—C11A—C12A	155.2 (4)
C2—C1—C11—C16	−159.1 (4)	C2A—C1A—C11A—C12A	−24.5 (6)
O1—C1—C11—C12	−155.7 (4)	O1A—C1A—C11A—C16A	−21.9 (6)
C2—C1—C11—C12	24.4 (6)	C2A—C1A—C11A—C16A	158.5 (4)
C16—C11—C12—C13	−0.3 (7)	C16A—C11A—C12A—C13A	0.7 (7)
C1—C11—C12—C13	176.2 (4)	C1A—C11A—C12A—C13A	−176.3 (4)
C11—C12—C13—C14	0.4 (7)	C11A—C12A—C13A—C14A	−1.1 (7)
C12—C13—C14—F1	179.2 (4)	C12A—C13A—C14A—F1A	−179.1 (4)
C12—C13—C14—C15	0.0 (7)	C12A—C13A—C14A—C15A	0.5 (7)
C13—C14—C15—C16	−0.4 (7)	C13A—C14A—C15A—C16A	0.4 (7)
F1—C14—C15—C16	−179.6 (4)	F1A—C14A—C15A—C16A	180.0 (4)
C14—C15—C16—C11	0.5 (7)	C14A—C15A—C16A—C11A	−0.8 (7)
C12—C11—C16—C15	−0.1 (7)	C12A—C11A—C16A—C15A	0.2 (7)
C1—C11—C16—C15	−176.7 (4)	C1A—C11A—C16A—C15A	177.3 (4)
C2—C3—C21—C22	−171.9 (4)	C2A—C3A—C21A—C22A	173.2 (4)
C2—C3—C21—C26	10.1 (7)	C2A—C3A—C21A—C26A	−9.2 (7)
C26—C21—C22—C23	0.2 (6)	C26A—C21A—C22A—C23A	0.9 (6)
C3—C21—C22—C23	−177.9 (4)	C3A—C21A—C22A—C23A	178.7 (4)
C21—C22—C23—C24	−0.5 (6)	C21A—C22A—C23A—C24A	−1.1 (6)
C22—C23—C24—C25	1.0 (6)	C22A—C23A—C24A—C25A	0.2 (6)
C22—C23—C24—C31	−179.4 (4)	C22A—C23A—C24A—C31A	−179.2 (4)
C23—C24—C25—C26	−1.3 (6)	C23A—C24A—C25A—C26A	0.8 (6)
C31—C24—C25—C26	179.2 (4)	C31A—C24A—C25A—C26A	−179.8 (4)
C24—C25—C26—C21	1.0 (6)	C24A—C25A—C26A—C21A	−0.9 (6)
C22—C21—C26—C25	−0.5 (6)	C22A—C21A—C26A—C25A	0.0 (6)
C3—C21—C26—C25	177.5 (4)	C3A—C21A—C26A—C25A	−177.6 (4)
C23—C24—C31—C32	3.4 (6)	C23A—C24A—C31A—C36A	179.0 (4)
C25—C24—C31—C32	−177.1 (4)	C25A—C24A—C31A—C36A	−0.4 (6)
C23—C24—C31—C36	−176.4 (4)	C23A—C24A—C31A—C32A	−2.7 (6)
C25—C24—C31—C36	3.2 (6)	C25A—C24A—C31A—C32A	178.0 (4)
C36—C31—C32—C33	1.5 (6)	C36A—C31A—C32A—C33A	−2.4 (6)
C24—C31—C32—C33	−178.3 (4)	C24A—C31A—C32A—C33A	179.2 (4)
C31—C32—C33—C34	−2.0 (7)	C31A—C32A—C33A—C34A	0.6 (7)
C32—C33—C34—C35	0.9 (7)	C32A—C33A—C34A—C35A	0.5 (7)
C33—C34—C35—C36	0.7 (6)	C33A—C34A—C35A—C36A	0.2 (6)
C34—C35—C36—C31	−1.3 (6)	C34A—C35A—C36A—C31A	−2.1 (6)
C32—C31—C36—C35	0.2 (6)	C32A—C31A—C36A—C35A	3.1 (6)
C24—C31—C36—C35	179.9 (4)	C24A—C31A—C36A—C35A	−178.5 (4)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅FO
M_r	302.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	6.0095 (5), 35.278 (3), 7.2352 (6)
β (°)	90.018 (7)
V (Å³)	1533.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.23 × 0.07

Data collection
Diffractometer	STOE IPDS II two-circle- diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11797, 2748, 2247
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.150, 1.08
No. of reflections	2748
No. of parameters	416
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003), SHELXL97.

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3-(Biphen­yl-4-yl)-1-(4-fluoro­phen­yl)prop-2-en-1-one

Supporting information

Key indicators

checkCIF/PLATON results

3-(Biphenyl-4-yl)-1-(4-fluorophenyl)prop-2-en-1-one