A series of substituted (2E)-3-(2-fluoro-4-phenoxy­phen­yl)-1-phenyl­prop-2-en-1-ones

In the mol­ecular structures of a series of substituted chalcones, namely (2E)-3-(2-fluoro-4-phenoxy­phen­yl)-1-phenyl­prop-2-en-1-one, C₂₁H₁₅FO₂, (I), (2E)-3-(2-fluoro-4-phenoxy­phen­yl)-1-(4-fluoro­phen­yl)prop-2-en-1-one, C₂₁H₁₄F₂O₂, (II), (2E)-1-(4-chloro­phen­yl)-3-(2-fluoro-4-phenoxy­phen­yl)prop-2-en-1-one, C₂₁H₁₄ClFO₂, (III), (2E)-3-(2-fluoro-4-phenoxy­phen­yl)-1-(4-methyl­phen­yl)prop-2-en-1-one, C₂₂H₁₇FO₂, (IV), and (2E)-3-(2-fluoro-4-phenoxy­phen­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one, C₂₂H₁₇FO₃, (V), the configuration of the keto group with respect to the olefinic double bond is s-cis. The mol­ecules pack utilizing weak C—H...O and C—H...π inter­molecular contacts. Identical packing motifs involving C—H...O inter­actions, forming both chains and dimers, along with C—H...π dimers and π–π aromatic inter­actions are observed in the fluoro, chloro and methyl derivatives.

S1. Comment

Chalcones are an important class of organic compounds, belonging to the biogenetic precursors of the flavonoids in higher plants, and these find potential applications in widespread biological activities, viz. antibacterial, antifungal and anti-inflammatory drugs (Ahluwalia et al., 1986; Achenbach et al., 1988; Bhat et al., 1972; Masaoud et al. 1995; Mathew et al., 1984; Oganesyan et al., 1986; Sinz et al., 1999; Thuy et al., 1998). The essential feature of chalcone derivatives is the carbonyl functional group, which has a pivotal role in the observed antibacterial activity of such compounds. In addition, antimicrobial, antiviral, antitumoral, antimutagenic, antimitotic, anti-inflammatory, anti-ulcerative and hepatoprotective activities and applications of therapeutic effects have been also reported (Arty et al., 2000; Batt et al., 1993; Hu et al., 1994; Iwata et al., 1995; Lorimer & Perry, 1994; Mahmood et al.,1997; Markham et al., 1987; Min et al., 1996; Pappano et al., 1985, 1990, 1994; Sogawa et al., 1994; Williams et al., 1995). Since some chalcones are found to inhibit various enzymes, involving the reaction of reactive oxygen species (5-lipoxygenase, 12-lipoxygenase, cyclooxygenase etc.), the majority of their pharmacological properties are supposed to be related to their antioxidative effect (Forejtnikova et al., 2005; Sogawa et al., 1994). In the literature, there are reports on structure–activity correlations carried out on such classes of compounds (Debattista et al., 1986; Dhar, 1961). These compounds have also been used as starting (precursor) materials in many synthetic reactions (Awad et al., 1960; Carrie & Rochard, 1963; Coudert et al., 1988; Nel et al., 1998). Substituted chalcones have been synthesized and used as fluorescent probes (Jiang et al., 1994). In particular, chalcone derivatives with typical D-p-A mode have been reported to possess intense fluorescence properties. For example, dimethylaminochalcone (DMAC) has been reported to be a potential chemosensor (Di Cesare & Lakowicz, 2002). These have also been found to exhibit potential nonlinear optical properties (Wang & Wu, 1994; Fichou et al., 1988). Differently substituted chalcones have been investigated in detail in the solid state to understand the structural feautures associated with these compounds (Lokaj et al., 2001; Low et al., 2002; Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al., 2005), and references therein; Moorthi et al. (2005); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al., 2005; Ravishankar, Chinnakali, Nanjundan, Selvam & Yu, 2005; Schmalle et al., 1990; Wang et al., 2004). The phenomenon of polymorphism has also been explored in such compounds, a very important case being bavachalcone (Ravikumar et al., 2005), a bioactive compound extracted from the seed of Psoralea corylifolia, which has been widely applied for the cure of bleeding, vitiligo and psoriasis, leucoderma, bone fracture and osteoporosis (Kondo et al., 1990; Miura et al., 1996; Yin et al., 2004).

In order to understand the geometrical features and the underlying intermolecular interactions, which hold the assembly of molecules in the crystalline lattice, we have studied a series of substituted chalcones and analyzed the conformational and packing features. Weak intermolecular C—H···O, C—H···π and π–π interactions generate different packing motifs in the crystalline lattice.

Figs. 1–5 depict the structures of all the molecules. Compound (I) (Fig. 1) crystallizes in the monoclinic space group with Z = 4. Compounds (II)–(V) (Figs. 2–5) crystallize in the triclinic centrosymmetric space group. The H atom of the central propenone group is trans with respect to the C8═C9 double bond. The dihedral angles between the C10–C15/F1 and C1–C6 phenyl rings (A and B) and the dihedral angles between these rings and the O1═C7—C8═C9 group are given in Table 11. An analysis of the weighted least-squares plane through the central C4/C7/O1/C8/C9/C10 chain shows that atoms C8 and C9 are displaced by the distances given in Table 12.

The C8═C9 double-bond lengths in all of the compounds are in agreement with the expected values reported in the literature (Allen et al., 1987; Allen, 2002; Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al., 2005), and references therein; Moorthi et al. (2005); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al., 2005; Tables 1, 3, 5, 7 and 9). However, the C8—C9—C10 bond angle deviates from an ideal value of 120° as a result of the steric interaction between atoms H15 on ring A and H8, attached to the C8═C9 double bond (Sathiya Moorthi, Chinnakali, Nanjundan, Radhika et al., 2005), and references therein; Moorthi et al. (2005); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam et al., 2005). This is a common feature observed in all the compounds.

In (I), the intermolecular interactions that characterize the packing of molecules are C—H···π interactions involving atoms H6 and H14, forming alternate dimers in the crystalline lattice with rings A (center of gravity is denoted as Cg1) and B (center of gravity is denoted as Cg2) respectively (Fig. 6 and Table 2).

On replacement of the H atom at the para position (C1) by an F atom in (II), the electron-donating mesomeric effect of the lone pairs on the F atom on ring A leads to extended conjugation, the dihedral angle being 4.29 (8)°. The packing of molecules (Fig. 7 and Table 4) in the crystal structure is via two different types of C—H···O interaction, one forming chains along the crystallographic b axis (involving atom H18) [graph-set symbol C(12)] and the other forming dimers (involving atom H11) [graph-set symbol R₂²(14)]. C—H···π interactions, involving atom H14 and the C16–C21 ring (C), forming molecular chains along the a axis, further hold such molecules, leading to the formation of a sheet-like structure.

On replacement of the F atom by a Cl atom in (III), the crystal packing is unchanged. The same H atoms (H11 and H18) are involved in the formation of identical packing motifs (Fig. 8 and Table 6). Such C—H···O interactions generate tetrameric motifs, consisting of R₂⁴(32) and R₂⁴(22) units. Furthermore, C—H···π dimers, involving atom H5 and ring C, link consecutive terameric units together in the crystal structure.

Similar packing characteristics are observed in the case of the methyl derivative, (IV). Identical C—H···O and C—H···π intermolecular contacts steer the packing of molecules in the crystal structure (Fig. 9 and Table 5). In addition to these interactions, the crystal structure is further stabilized by aromatic π–π stacking interactions involving rings A and B; the distances are in the range 3.862 (3)–3.880 (3) Å in the fluoro, chloro and methyl derivatives, respectively.

In the case of (V), the presence of a methoxy group generates different packing motifs, wherein the crystal structure is stabilized by two different C—H···O dimers involving atoms H18 and H3 with atoms O3 and O1 [graph-set symbols R₂²(32) and R₂²(12)], forming dimeric motifs. Furthermore, C—H···π dimers, involving atom H21 and ring B, reinforce the existing C—H···O dimers, providing additional stability (Fig. 10 and Table 6).

It is of interest to note that the packing of molecules in all the crystal structures is dictated by weak intermolecular interactions of the C—H···O and C—H···π types.

Related literature

For related literature, see: Achenbach et al. (1988); Ahluwalia et al. (1986); Allen (2002); Allen et al. (1987); Arty et al. (2000); Awad et al. (1960); Batt et al. (1993); Bhat et al. (1972); Carrie & Rochard (1963); Coudert et al. (1988); Debattista et al. (1986); Dhar (1961); Di & Lakowicz (2002); Fichou et al. (1988); Forejtnikova et al. (2005); Hu et al. (1994); Iwata et al. (1995); Jiang et al. (1994); Kondo et al. (1990); Lokaj et al. (2001); Lorimer & Perry (1994); Low et al. (2002); Mahmood et al. (1997); Markham et al. (1987); Masaoud et al. (1995); Mathew et al. (1984); Min et al. (1996); Miura et al. (1996); Mohan (2006); Moorthi et al. (2005); Nel et al. (1998); Oganesyan et al. (1986); Pappano et al. (1985, 1990, 1994); Ravikumar et al. (2005); Ravishankar et al. (2005); Sathiya Moorthi, Chinnakali, Nanjundan, Radhika, Fun & Yu (2005); Sathiya Moorthi, Chinnakali, Nanjundan, Selvam, Fun & Yu (2005); Schmalle et al. (1990); Sinz et al. (1999); Sogawa et al. (1994); Thuy et al. (1998); Wang & Wu (1994); Wang et al. (2004); Williams et al. (1995); Yin et al. (2004).

S2. Experimental

To a thoroughly stirred solution of substituted acetophenone (0.01 mol) and 4-fluoro-3-phenoxybezaldehyde (0.01 mol) in methanol (25 ml), 40% aqueous NaOH solution (100 ml) was added at room temperature; the mixture was heated for 10 min and left overnight. It was then poured into ice–water and the precipitated product was filtered off. The crude product was recrystallized from hexane. The synthesized product was characterized by melting point meaurements, and IR, NMR and mass spectroscopy (Mohan, 2006). This was again taken in 5.0 ml beakers and a series of crystallization experiments were performed in solvents such as acetone, ethylacetate/hexane, dichloromethane and dichloromethane/hexane. In all the cases, the crystals on which the final data were collected were grown from acetone.

S3. Refinement

In all the five compounds, H atoms were located from difference Fourier maps and refined isotropically. The C—H bond lengths are in the range 0.87 (2)–1.05 (2) Å.

Computing details

For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

	Fig. 1. The molecular structure of (I), drawn with 50% ellipsoidal probability and showing the atom-labelling scheme.
	Fig. 2. The molecular structure of (II), drawn with 50% ellipsoidal probability and showing the atom-labelling scheme.
	Fig. 3. The molecular structure of (III), drawn with 50% ellipsoidal probability and showing the atom-labelling scheme.
	Fig. 4. The molecular structure of (IV), drawn with 50% ellipsoidal probability and showing the atom-labelling scheme.
	Fig. 5. : The molecular structure of (V), drawn with 50% ellipsoidal probability and showing the atom-labelling scheme.
	Fig. 6. : A partial packing diagram for (I), depicting C—H···π dimers. Molecules labeled # and * have the symmetry codes (-x, -y + 1, -z) and (-x + 1, - y + 1, -z), respectively. Cg1 and Cg2 are the centers of gravity of the C10–C15 and C1–C6 phenyl rings. The dotted lines indicate intermolecular interactions.
	Fig. 7. : A partial packing diagram for (II), depicting C—H···O and C—H···π interactions forming dimers and chains. Molecules labeled ', ", # and * have the symmetry codes (-x + 1, -y + 1, -z), (x - 1, y, z), (-x, -y, -z + 2) and (x, y + 1, z), respectively. The dotted lines indicate intermolecular interactions. Cg3 is the center of gravity of the C16–C21 phenyl ring.
	Fig. 8. : A partial packing diagram for (III), depicting C—H···O and C—H···π interactions. Molecules labeled #, * and " have the symmetry codes (-x, -y, -z + 2), (x, y + 1, z) and (-x + 1, -y + 1, -z), respectively. The dotted lines indicate intermolecular interactions. Cg3 is the center of gravity of the C16–C21 phenyl ring.
	Fig. 9. : C—H···O and C—H···.π intermolecular interactions highlighting the packing features in (IV). Molecules labeled #, * and " have the symmetry codes (-x, -y, -z + 2), (x, y + 1, z) and (-x + 1, -y + 1, -z), respectively, with Cg3 denoting the center of gravity of the C16–C21 phenyl ring.
	Fig. 10. : A partial packing diagram for (V), depicting C—H···O and C—H···π dimers. Molecules labeled #, " and * have the symmetry codes (- x + 2, - y - 1, - z + 1), (- x + 2, - y, - z + 1) and (- x + 1, - y, - z + 1), respectively. The dotted lines indicate intermolecular interactions. Cg2 is the center of gravity of the C1–C6 phenyl ring.

(I) (2E)-3-(2-fluoro-4-phenoxyphenyl)-1-phenylprop-2-en-1-one

Crystal data

C21H15FO2	F(000) = 664
Mr = 318.33	Dx = 1.330 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 835 reflections
a = 7.2869 (17) Å	θ = 1.4–25.2°
b = 5.9407 (14) Å	µ = 0.09 mm^−1
c = 36.805 (8) Å	T = 290 K
β = 93.724 (4)°	Block, colorless
V = 1589.9 (6) Å^3	0.56 × 0.40 × 0.24 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3220 independent reflections
Radiation source: fine-focus sealed tube	2748 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ϕ and ω scans	θmax = 26.4°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.929, Tmax = 0.978	k = −7→7
11668 measured reflections	l = −45→45

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	All H-atom parameters refined
S = 1.21	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.4268P] where P = (Fo^2 + 2Fc^2)/3
3220 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.15 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	0.5142 (2)	0.3032 (2)	0.17115 (4)	0.0808 (4)
O1	0.2403 (2)	1.1937 (2)	0.00204 (4)	0.0726 (5)
O2	0.37504 (19)	0.7175 (3)	0.18472 (4)	0.0664 (4)
C1	0.0876 (3)	0.8622 (4)	−0.11942 (5)	0.0579 (5)
C2	0.1639 (3)	1.0661 (4)	−0.10864 (5)	0.0550 (5)
C3	0.2107 (2)	1.1061 (3)	−0.07233 (5)	0.0477 (4)
C4	0.1862 (2)	0.9405 (3)	−0.04632 (5)	0.0421 (4)
C5	0.1111 (2)	0.7340 (3)	−0.05747 (5)	0.0487 (4)
C6	0.0597 (3)	0.6971 (4)	−0.09407 (6)	0.0553 (5)
C7	0.2336 (2)	0.9963 (3)	−0.00741 (5)	0.0485 (4)
C8	0.2748 (3)	0.8134 (3)	0.01898 (5)	0.0506 (4)
C9	0.2815 (2)	0.8544 (3)	0.05447 (5)	0.0459 (4)
C10	0.3345 (2)	0.7006 (3)	0.08427 (5)	0.0427 (4)
C11	0.3215 (2)	0.7736 (3)	0.12008 (5)	0.0469 (4)
C12	0.3792 (2)	0.6407 (3)	0.14930 (5)	0.0500 (4)
C13	0.4539 (2)	0.4327 (3)	0.14262 (5)	0.0532 (5)
C14	0.4684 (3)	0.3549 (3)	0.10764 (6)	0.0541 (5)
C15	0.4082 (2)	0.4873 (3)	0.07860 (5)	0.0475 (4)
C16	0.2028 (3)	0.7760 (3)	0.19599 (4)	0.0509 (4)
C17	0.1899 (3)	0.9730 (4)	0.21513 (6)	0.0633 (5)
C18	0.0221 (4)	1.0323 (5)	0.22768 (6)	0.0789 (7)
C19	−0.1291 (4)	0.8977 (6)	0.22112 (6)	0.0851 (8)
C20	−0.1133 (4)	0.7002 (5)	0.20257 (6)	0.0788 (7)
C21	0.0536 (3)	0.6372 (4)	0.18984 (6)	0.0648 (6)
H1	0.050 (3)	0.835 (4)	−0.1459 (6)	0.066 (6)*
H2	0.184 (3)	1.181 (4)	−0.1271 (6)	0.068 (6)*
H3	0.261 (3)	1.250 (3)	−0.0643 (5)	0.048 (5)*
H5	0.092 (3)	0.619 (3)	−0.0396 (5)	0.054 (5)*
H6	0.008 (3)	0.553 (4)	−0.1015 (5)	0.062 (6)*
H8	0.303 (3)	0.668 (4)	0.0102 (6)	0.065 (6)*
H9	0.251 (3)	1.006 (4)	0.0623 (5)	0.057 (5)*
H11	0.268 (3)	0.920 (4)	0.1250 (5)	0.057 (5)*
H14	0.519 (3)	0.209 (4)	0.1053 (6)	0.070 (6)*
H15	0.420 (2)	0.432 (3)	0.0544 (5)	0.051 (5)*
H17	0.297 (3)	1.060 (4)	0.2181 (6)	0.072 (7)*
H18	0.013 (4)	1.172 (5)	0.2407 (8)	0.100 (9)*
H19	−0.247 (4)	0.942 (5)	0.2300 (8)	0.104 (9)*
H20	−0.214 (4)	0.600 (5)	0.1984 (7)	0.099 (9)*
H21	0.070 (3)	0.499 (4)	0.1772 (6)	0.077 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0874 (9)	0.0802 (9)	0.0730 (8)	0.0148 (7)	−0.0078 (7)	0.0232 (7)
O1	0.1163 (13)	0.0475 (8)	0.0537 (8)	−0.0015 (8)	0.0031 (8)	−0.0081 (6)
O2	0.0587 (8)	0.0946 (11)	0.0448 (7)	0.0081 (8)	−0.0050 (6)	−0.0080 (7)
C1	0.0575 (11)	0.0670 (13)	0.0481 (11)	0.0118 (9)	−0.0052 (9)	−0.0062 (9)
C2	0.0599 (11)	0.0561 (11)	0.0490 (10)	0.0092 (9)	0.0037 (9)	0.0079 (9)
C3	0.0473 (9)	0.0427 (10)	0.0533 (10)	0.0030 (8)	0.0046 (8)	0.0003 (8)
C4	0.0393 (8)	0.0428 (9)	0.0446 (9)	0.0050 (7)	0.0062 (7)	−0.0013 (7)
C5	0.0490 (10)	0.0443 (10)	0.0537 (10)	0.0009 (8)	0.0095 (8)	−0.0006 (8)
C6	0.0519 (10)	0.0527 (11)	0.0606 (12)	−0.0004 (9)	−0.0014 (8)	−0.0123 (9)
C7	0.0530 (10)	0.0468 (10)	0.0463 (10)	0.0018 (8)	0.0082 (8)	−0.0047 (8)
C8	0.0572 (11)	0.0476 (10)	0.0474 (10)	0.0059 (8)	0.0061 (8)	−0.0044 (8)
C9	0.0455 (9)	0.0449 (10)	0.0477 (10)	0.0025 (7)	0.0050 (7)	−0.0038 (8)
C10	0.0347 (8)	0.0465 (9)	0.0472 (9)	0.0000 (7)	0.0041 (7)	−0.0032 (7)
C11	0.0444 (9)	0.0486 (10)	0.0475 (10)	0.0059 (8)	0.0030 (7)	−0.0046 (8)
C12	0.0428 (9)	0.0615 (11)	0.0452 (9)	0.0010 (8)	0.0005 (7)	−0.0027 (8)
C13	0.0454 (10)	0.0565 (11)	0.0570 (11)	0.0027 (8)	−0.0020 (8)	0.0107 (9)
C14	0.0473 (10)	0.0447 (10)	0.0700 (13)	0.0057 (8)	0.0031 (9)	−0.0014 (9)
C15	0.0431 (9)	0.0489 (10)	0.0511 (10)	0.0021 (7)	0.0067 (7)	−0.0069 (8)
C16	0.0596 (11)	0.0613 (11)	0.0315 (8)	−0.0008 (9)	−0.0003 (7)	0.0027 (8)
C17	0.0725 (14)	0.0676 (14)	0.0495 (11)	−0.0092 (11)	0.0005 (10)	−0.0041 (10)
C18	0.0943 (19)	0.0838 (17)	0.0595 (13)	0.0086 (14)	0.0126 (12)	−0.0190 (12)
C19	0.0713 (15)	0.130 (2)	0.0550 (13)	0.0028 (16)	0.0157 (11)	−0.0117 (15)
C20	0.0726 (15)	0.113 (2)	0.0520 (12)	−0.0283 (15)	0.0099 (11)	−0.0017 (13)
C21	0.0798 (14)	0.0675 (14)	0.0473 (11)	−0.0151 (11)	0.0047 (10)	−0.0048 (10)

Geometric parameters (Å, º)

C5—C6	1.392 (3)	C11—H11	0.97 (2)
C5—C4	1.394 (3)	C14—C13	1.378 (3)
C5—H5	0.97 (2)	C14—H14	0.95 (2)
C10—C11	1.397 (2)	C16—C21	1.371 (3)
C10—C15	1.397 (2)	C16—C17	1.372 (3)
C10—C9	1.460 (2)	C2—C1	1.380 (3)
F1—C13	1.352 (2)	C2—H2	0.98 (2)
C3—C2	1.378 (3)	C1—C6	1.378 (3)
C3—C4	1.392 (2)	C1—H1	1.01 (2)
C3—H3	0.968 (19)	C12—C13	1.378 (3)
C9—C8	1.327 (3)	C6—H6	0.97 (2)
C9—H9	0.97 (2)	C17—C18	1.381 (3)
O1—C7	1.224 (2)	C17—H17	0.94 (2)
O2—C12	1.384 (2)	C21—C20	1.383 (3)
O2—C16	1.392 (2)	C21—H21	0.96 (3)
C15—C14	1.376 (3)	C20—C19	1.366 (4)
C15—H15	0.958 (19)	C20—H20	0.95 (3)
C8—C7	1.475 (3)	C18—C19	1.370 (4)
C8—H8	0.95 (2)	C18—H18	0.96 (3)
C4—C7	1.489 (2)	C19—H19	0.98 (3)
C11—C12	1.378 (3)
C6—C5—C4	119.93 (18)	C21—C16—O2	121.43 (19)
C6—C5—H5	120.5 (12)	C17—C16—O2	117.30 (19)
C4—C5—H5	119.5 (12)	C3—C2—C1	119.99 (19)
C11—C10—C15	118.22 (17)	C3—C2—H2	120.9 (13)
C11—C10—C9	118.92 (16)	C1—C2—H2	119.1 (13)
C15—C10—C9	122.75 (16)	C6—C1—C2	120.29 (19)
C2—C3—C4	120.66 (18)	C6—C1—H1	119.8 (13)
C2—C3—H3	120.9 (11)	C2—C1—H1	119.9 (13)
C4—C3—H3	118.5 (11)	C11—C12—C13	118.59 (17)
C8—C9—C10	128.00 (18)	C11—C12—O2	121.46 (18)
C8—C9—H9	117.8 (12)	C13—C12—O2	119.80 (17)
C10—C9—H9	114.2 (12)	F1—C13—C12	118.91 (18)
C12—O2—C16	116.03 (14)	F1—C13—C14	119.59 (18)
C14—C15—C10	120.59 (18)	C12—C13—C14	121.50 (17)
C14—C15—H15	118.7 (11)	C1—C6—C5	120.09 (19)
C10—C15—H15	120.7 (11)	C1—C6—H6	120.7 (12)
C9—C8—C7	120.39 (18)	C5—C6—H6	119.2 (12)
C9—C8—H8	120.5 (13)	C16—C17—C18	118.7 (2)
C7—C8—H8	119.1 (13)	C16—C17—H17	116.4 (14)
C3—C4—C5	119.00 (17)	C18—C17—H17	124.9 (14)
C3—C4—C7	118.17 (16)	C16—C21—C20	119.1 (2)
C5—C4—C7	122.76 (16)	C16—C21—H21	118.4 (14)
C12—C11—C10	121.49 (17)	C20—C21—H21	122.5 (14)
C12—C11—H11	118.2 (12)	C19—C20—C21	120.4 (2)
C10—C11—H11	120.2 (12)	C19—C20—H20	122.1 (17)
O1—C7—C8	121.10 (17)	C21—C20—H20	117.4 (17)
O1—C7—C4	119.27 (17)	C19—C18—C17	120.8 (2)
C8—C7—C4	119.62 (16)	C19—C18—H18	120.6 (17)
C15—C14—C13	119.58 (18)	C17—C18—H18	118.6 (17)
C15—C14—H14	124.0 (14)	C20—C19—C18	119.7 (2)
C13—C14—H14	116.5 (14)	C20—C19—H19	120.3 (18)
C21—C16—C17	121.2 (2)	C18—C19—H19	119.9 (17)
C11—C10—C9—C8	−176.10 (18)	C3—C2—C1—C6	−0.7 (3)
C15—C10—C9—C8	7.7 (3)	C10—C11—C12—C13	1.0 (3)
C11—C10—C15—C14	−0.9 (3)	C10—C11—C12—O2	176.63 (16)
C9—C10—C15—C14	175.26 (16)	C16—O2—C12—C11	60.7 (2)
C10—C9—C8—C7	−174.49 (17)	C16—O2—C12—C13	−123.75 (19)
C2—C3—C4—C5	−0.9 (3)	C11—C12—C13—F1	178.75 (16)
C2—C3—C4—C7	−178.07 (16)	O2—C12—C13—F1	3.0 (3)
C6—C5—C4—C3	−0.9 (3)	C11—C12—C13—C14	−1.2 (3)
C6—C5—C4—C7	176.23 (16)	O2—C12—C13—C14	−176.93 (17)
C15—C10—C11—C12	0.1 (3)	C15—C14—C13—F1	−179.60 (16)
C9—C10—C11—C12	−176.28 (16)	C15—C14—C13—C12	0.4 (3)
C9—C8—C7—O1	14.4 (3)	C2—C1—C6—C5	−1.0 (3)
C9—C8—C7—C4	−166.65 (16)	C4—C5—C6—C1	1.8 (3)
C3—C4—C7—O1	21.1 (3)	C21—C16—C17—C18	−1.2 (3)
C5—C4—C7—O1	−156.02 (19)	O2—C16—C17—C18	−178.01 (19)
C3—C4—C7—C8	−157.94 (16)	C17—C16—C21—C20	1.3 (3)
C5—C4—C7—C8	25.0 (2)	O2—C16—C21—C20	178.05 (19)
C10—C15—C14—C13	0.7 (3)	C16—C21—C20—C19	−0.2 (4)
C12—O2—C16—C21	47.6 (3)	C16—C17—C18—C19	−0.2 (4)
C12—O2—C16—C17	−135.57 (19)	C21—C20—C19—C18	−1.1 (4)
C4—C3—C2—C1	1.6 (3)	C17—C18—C19—C20	1.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1^i	0.97 (3)	3.02 (2)	3.685 (2)	127 (2)
C14—H14···Cg2^ii	0.95 (2)	2.77 (2)	3.429 (2)	128 (2)

Symmetry codes: (i) −x+1/2, y+3/2, −z+1/2; (ii) −x+3/2, y+3/2, −z+1/2.

(II) (2E)-3-(2-fluoro-4-phenoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one

Crystal data

C21H14F2O2	Z = 2
Mr = 336.32	F(000) = 348
Triclinic, P1	Dx = 1.351 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.164 (5) Å	Cell parameters from 775 reflections
b = 10.036 (6) Å	θ = 1.4–25.2°
c = 11.136 (7) Å	µ = 0.10 mm^−1
α = 97.362 (10)°	T = 290 K
β = 101.898 (9)°	Plate, colorless
γ = 108.731 (9)°	0.23 × 0.20 × 0.06 mm
V = 826.8 (9) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3291 independent reflections
Radiation source: fine-focus sealed tube	2205 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ϕ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.944, Tmax = 0.994	k = −12→12
8638 measured reflections	l = −13→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0622P)^2 + 0.0408P] where P = (Fo^2 + 2Fc^2)/3
3291 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.19 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	0.37217 (15)	0.54948 (11)	0.68943 (10)	0.0887 (4)
F2	0.83443 (16)	−0.04147 (15)	1.56720 (12)	0.1073 (4)
O1	0.21063 (19)	−0.08620 (17)	1.11312 (13)	0.1068 (5)
O2	0.03588 (16)	0.36217 (12)	0.67485 (11)	0.0756 (4)
C1	0.7219 (3)	−0.0300 (2)	1.46365 (17)	0.0717 (5)
C2	0.5551 (3)	−0.1331 (2)	1.41942 (18)	0.0711 (5)
C3	0.4404 (3)	−0.11863 (18)	1.31695 (16)	0.0647 (4)
C4	0.4925 (2)	−0.00337 (15)	1.25774 (13)	0.0537 (4)
C5	0.6633 (2)	0.09816 (18)	1.30612 (16)	0.0629 (4)
C6	0.7799 (3)	0.0859 (2)	1.41007 (18)	0.0737 (5)
C7	0.3617 (2)	0.00398 (18)	1.14640 (15)	0.0631 (4)
C8	0.4118 (2)	0.11838 (18)	1.07501 (15)	0.0595 (4)
C9	0.2936 (2)	0.13165 (18)	0.98114 (15)	0.0620 (4)
C10	0.3201 (2)	0.23957 (16)	0.90318 (14)	0.0557 (4)
C11	0.1693 (2)	0.25153 (18)	0.82563 (15)	0.0615 (4)
C12	0.1868 (2)	0.35544 (17)	0.75469 (14)	0.0615 (4)
C13	0.3558 (2)	0.44685 (17)	0.75926 (15)	0.0634 (4)
C14	0.5068 (2)	0.43697 (19)	0.83293 (16)	0.0642 (4)
C15	0.4880 (2)	0.33308 (17)	0.90426 (15)	0.0592 (4)
C16	−0.0158 (2)	0.47810 (16)	0.70489 (15)	0.0606 (4)
C17	0.0394 (2)	0.5635 (2)	0.82288 (19)	0.0729 (5)
C18	−0.0181 (3)	0.6791 (2)	0.8418 (3)	0.0882 (6)
C19	−0.1305 (3)	0.7051 (3)	0.7448 (3)	0.0926 (7)
C20	−0.1876 (3)	0.6162 (3)	0.6296 (2)	0.0905 (7)
C21	−0.1322 (2)	0.5024 (2)	0.6085 (2)	0.0732 (5)
H2	0.517 (2)	−0.2113 (19)	1.4593 (17)	0.079 (5)*
H3	0.323 (3)	−0.187 (2)	1.2838 (17)	0.081 (6)*
H5	0.706 (2)	0.1796 (18)	1.2666 (15)	0.070 (5)*
H6	0.895 (3)	0.154 (2)	1.4414 (18)	0.089 (6)*
H8	0.531 (3)	0.1797 (19)	1.0988 (16)	0.078 (5)*
H9	0.175 (3)	0.0639 (19)	0.9656 (17)	0.084 (6)*
H11	0.053 (2)	0.1887 (17)	0.8247 (14)	0.063 (4)*
H14	0.621 (3)	0.4998 (19)	0.8320 (16)	0.076 (5)*
H15	0.592 (2)	0.3252 (16)	0.9564 (15)	0.063 (4)*
H17	0.112 (2)	0.5395 (18)	0.8877 (17)	0.072 (5)*
H18	0.022 (3)	0.731 (2)	0.921 (2)	0.093 (7)*
H19	−0.168 (3)	0.786 (2)	0.7597 (19)	0.103 (7)*
H20	−0.273 (3)	0.634 (2)	0.558 (2)	0.114 (7)*
H21	−0.168 (3)	0.442 (2)	0.529 (2)	0.089 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0936 (8)	0.0794 (7)	0.0896 (7)	0.0256 (6)	0.0132 (6)	0.0376 (6)
F2	0.0981 (9)	0.1437 (10)	0.1014 (9)	0.0654 (8)	0.0143 (7)	0.0608 (8)
O1	0.0707 (9)	0.1173 (11)	0.0876 (10)	−0.0166 (8)	−0.0064 (7)	0.0431 (8)
O2	0.0735 (8)	0.0682 (7)	0.0690 (7)	0.0288 (6)	−0.0133 (6)	0.0026 (6)
C1	0.0735 (12)	0.0908 (13)	0.0690 (11)	0.0482 (11)	0.0184 (9)	0.0305 (10)
C2	0.0871 (14)	0.0675 (11)	0.0747 (12)	0.0364 (10)	0.0322 (10)	0.0297 (9)
C3	0.0702 (12)	0.0575 (10)	0.0648 (10)	0.0188 (9)	0.0210 (9)	0.0123 (8)
C4	0.0568 (9)	0.0538 (8)	0.0530 (8)	0.0206 (7)	0.0186 (7)	0.0113 (7)
C5	0.0570 (10)	0.0652 (10)	0.0684 (10)	0.0212 (8)	0.0160 (8)	0.0236 (8)
C6	0.0564 (11)	0.0832 (12)	0.0794 (12)	0.0243 (10)	0.0098 (9)	0.0251 (10)
C7	0.0569 (10)	0.0669 (10)	0.0565 (9)	0.0115 (8)	0.0137 (8)	0.0114 (8)
C8	0.0535 (10)	0.0631 (9)	0.0564 (9)	0.0165 (8)	0.0103 (8)	0.0121 (7)
C9	0.0522 (10)	0.0679 (10)	0.0599 (10)	0.0163 (8)	0.0114 (8)	0.0120 (8)
C10	0.0543 (9)	0.0587 (9)	0.0501 (8)	0.0200 (7)	0.0084 (7)	0.0062 (7)
C11	0.0516 (10)	0.0629 (10)	0.0605 (10)	0.0157 (8)	0.0051 (8)	0.0081 (8)
C12	0.0613 (10)	0.0599 (9)	0.0545 (9)	0.0230 (8)	−0.0012 (7)	0.0050 (7)
C13	0.0711 (11)	0.0580 (9)	0.0585 (9)	0.0225 (8)	0.0114 (8)	0.0134 (8)
C14	0.0591 (10)	0.0632 (10)	0.0652 (10)	0.0162 (8)	0.0151 (8)	0.0130 (8)
C15	0.0511 (9)	0.0671 (10)	0.0559 (9)	0.0221 (8)	0.0082 (7)	0.0077 (8)
C16	0.0529 (9)	0.0578 (9)	0.0665 (10)	0.0144 (7)	0.0112 (8)	0.0186 (8)
C17	0.0587 (11)	0.0733 (11)	0.0759 (13)	0.0171 (9)	0.0095 (9)	0.0087 (10)
C18	0.0737 (13)	0.0807 (14)	0.0995 (17)	0.0138 (11)	0.0338 (13)	0.0002 (13)
C19	0.0917 (16)	0.0851 (15)	0.129 (2)	0.0449 (13)	0.0563 (16)	0.0413 (15)
C20	0.0977 (16)	0.1119 (17)	0.0970 (16)	0.0606 (14)	0.0436 (13)	0.0528 (15)
C21	0.0716 (12)	0.0881 (13)	0.0709 (12)	0.0356 (10)	0.0208 (10)	0.0332 (11)

Geometric parameters (Å, º)

C10—C15	1.387 (2)	C3—H3	0.944 (19)
C10—C11	1.400 (2)	C7—O1	1.219 (2)
C10—C9	1.463 (2)	C6—C1	1.369 (3)
F1—C13	1.3576 (19)	C6—C5	1.385 (2)
O2—C16	1.385 (2)	C6—H6	0.93 (2)
O2—C12	1.3895 (19)	C15—H15	0.959 (16)
C11—C12	1.376 (2)	C5—H5	0.978 (17)
C11—H11	0.953 (17)	C16—C17	1.373 (3)
C14—C13	1.373 (2)	C16—C21	1.382 (2)
C14—C15	1.379 (2)	C1—C2	1.362 (3)
C14—H14	0.947 (19)	C2—H2	0.949 (18)
C9—C8	1.321 (2)	C21—C20	1.368 (3)
C9—H9	0.955 (19)	C21—H21	0.94 (2)
C12—C13	1.376 (2)	C17—C18	1.392 (3)
C4—C5	1.382 (2)	C17—H17	0.946 (18)
C4—C3	1.396 (2)	C18—C19	1.376 (3)
C4—C7	1.487 (2)	C18—H18	0.90 (2)
C8—C7	1.478 (2)	C19—C20	1.361 (3)
C8—H8	0.932 (19)	C19—H19	0.97 (2)
F2—C1	1.361 (2)	C20—H20	1.02 (2)
C3—C2	1.375 (3)
C15—C10—C11	118.16 (15)	C1—C6—H6	121.0 (12)
C15—C10—C9	123.09 (14)	C5—C6—H6	120.7 (12)
C11—C10—C9	118.73 (15)	C14—C15—C10	121.24 (16)
C16—O2—C12	118.17 (12)	C14—C15—H15	119.9 (10)
C12—C11—C10	120.96 (16)	C10—C15—H15	118.9 (9)
C12—C11—H11	120.0 (9)	C4—C5—C6	121.08 (16)
C10—C11—H11	119.0 (9)	C4—C5—H5	120.8 (10)
C13—C14—C15	119.00 (16)	C6—C5—H5	118.1 (10)
C13—C14—H14	119.4 (10)	C17—C16—C21	120.76 (18)
C15—C14—H14	121.6 (10)	C17—C16—O2	123.35 (15)
C8—C9—C10	128.49 (16)	C21—C16—O2	115.87 (16)
C8—C9—H9	114.7 (11)	F2—C1—C2	118.42 (17)
C10—C9—H9	116.8 (11)	F2—C1—C6	118.64 (18)
C13—C12—C11	119.03 (15)	C2—C1—C6	122.92 (17)
C13—C12—O2	120.85 (15)	C1—C2—C3	118.09 (17)
C11—C12—O2	120.04 (15)	C1—C2—H2	121.6 (11)
C5—C4—C3	118.07 (15)	C3—C2—H2	120.3 (11)
C5—C4—C7	123.47 (14)	C20—C21—C16	119.6 (2)
C3—C4—C7	118.46 (15)	C20—C21—H21	121.3 (12)
C9—C8—C7	121.68 (16)	C16—C21—H21	119.0 (12)
C9—C8—H8	121.8 (11)	C16—C17—C18	118.5 (2)
C7—C8—H8	116.6 (11)	C16—C17—H17	118.3 (10)
C2—C3—C4	121.56 (18)	C18—C17—H17	123.3 (11)
C2—C3—H3	121.0 (11)	C19—C18—C17	120.6 (2)
C4—C3—H3	117.5 (11)	C19—C18—H18	124.8 (14)
O1—C7—C8	119.37 (16)	C17—C18—H18	114.6 (14)
O1—C7—C4	119.45 (15)	C20—C19—C18	119.8 (2)
C8—C7—C4	121.17 (14)	C20—C19—H19	120.8 (13)
F1—C13—C14	119.65 (15)	C18—C19—H19	119.4 (13)
F1—C13—C12	118.74 (15)	C19—C20—C21	120.7 (2)
C14—C13—C12	121.60 (15)	C19—C20—H20	119.9 (13)
C1—C6—C5	118.27 (18)	C21—C20—H20	119.4 (13)
C15—C10—C11—C12	−1.6 (2)	O2—C12—C13—C14	−176.72 (15)
C9—C10—C11—C12	177.14 (15)	C13—C14—C15—C10	−0.3 (2)
C15—C10—C9—C8	11.4 (3)	C11—C10—C15—C14	1.2 (2)
C11—C10—C9—C8	−167.27 (17)	C9—C10—C15—C14	−177.44 (15)
C10—C11—C12—C13	1.0 (2)	C3—C4—C5—C6	0.2 (2)
C10—C11—C12—O2	177.66 (13)	C7—C4—C5—C6	−179.90 (15)
C16—O2—C12—C13	−72.5 (2)	C1—C6—C5—C4	0.3 (3)
C16—O2—C12—C11	110.98 (18)	C12—O2—C16—C17	−18.9 (2)
C10—C9—C8—C7	178.70 (15)	C12—O2—C16—C21	162.58 (15)
C5—C4—C3—C2	−0.9 (2)	C5—C6—C1—F2	−178.81 (15)
C7—C4—C3—C2	179.22 (15)	C5—C6—C1—C2	−0.2 (3)
C9—C8—C7—O1	4.8 (3)	F2—C1—C2—C3	178.17 (15)
C9—C8—C7—C4	−175.44 (15)	C6—C1—C2—C3	−0.5 (3)
C5—C4—C7—O1	−176.52 (17)	C4—C3—C2—C1	1.0 (3)
C3—C4—C7—O1	3.4 (2)	C17—C16—C21—C20	2.5 (3)
C5—C4—C7—C8	3.7 (2)	O2—C16—C21—C20	−178.93 (16)
C3—C4—C7—C8	−176.41 (14)	C21—C16—C17—C18	−2.8 (3)
C15—C14—C13—F1	179.39 (14)	O2—C16—C17—C18	178.72 (16)
C15—C14—C13—C12	−0.2 (3)	C16—C17—C18—C19	1.2 (3)
C11—C12—C13—F1	−179.75 (14)	C17—C18—C19—C20	0.7 (3)
O2—C12—C13—F1	3.7 (2)	C18—C19—C20—C21	−1.1 (3)
C11—C12—C13—C14	−0.1 (3)	C16—C21—C20—C19	−0.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1^i	0.95 (2)	2.36 (2)	3.271 (3)	161 (2)
C18—H18···O1^ii	0.90 (2)	2.48 (2)	3.345 (3)	162 (2)
C5—H5···Cg3^iii	0.98 (2)	3.12 (2)	3.894 (3)	137 (1)
C14—H14···Cg3^iv	0.95 (2)	2.91 (2)	3.780 (3)	153 (1)

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

(III) (2E)-1-(4-chlorophenyl)-3-(2-fluoro-4-phenoxyphenyl)prop-2-en-1-one

Crystal data

C21H14ClFO2	Z = 2
Mr = 352.77	F(000) = 364
Triclinic, P1	Dx = 1.357 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.045 (6) Å	Cell parameters from 965 reflections
b = 9.833 (6) Å	θ = 1.8–25.6°
c = 11.474 (7) Å	µ = 0.24 mm^−1
α = 99.109 (7)°	T = 290 K
β = 104.800 (8)°	Block, colorless
γ = 113.697 (9)°	0.14 × 0.14 × 0.13 mm
V = 863.3 (9) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3395 independent reflections
Radiation source: fine-focus sealed tube	2672 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ϕ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.921, Tmax = 0.969	k = −12→12
8889 measured reflections	l = −14→14

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) = 0.134	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 0.1181P] where P = (Fo^2 + 2Fc^2)/3
3395 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.17 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
Cl1	0.80478 (8)	−0.08233 (8)	1.54625 (6)	0.0844 (2)
F1	0.3850 (2)	0.53648 (17)	0.67286 (14)	0.0977 (5)
O1	0.17510 (18)	−0.0423 (2)	1.12692 (15)	0.0821 (5)
O2	0.0572 (2)	0.35710 (18)	0.66076 (13)	0.0764 (5)
C1	0.6701 (3)	−0.0510 (2)	1.42744 (18)	0.0587 (5)
C2	0.4951 (3)	−0.1411 (3)	1.3894 (2)	0.0641 (5)
C3	0.3879 (3)	−0.1147 (3)	1.2967 (2)	0.0625 (5)
C4	0.4542 (2)	0.0022 (2)	1.24170 (17)	0.0531 (4)
C5	0.6326 (3)	0.0909 (3)	1.2821 (2)	0.0618 (5)
C6	0.7412 (3)	0.0657 (3)	1.3758 (2)	0.0665 (5)
C7	0.3295 (2)	0.0254 (2)	1.14370 (18)	0.0584 (5)
C8	0.3895 (3)	0.1278 (2)	1.06718 (19)	0.0592 (5)
C9	0.2777 (3)	0.1439 (3)	0.97700 (19)	0.0595 (5)
C10	0.3106 (2)	0.2425 (2)	0.89503 (17)	0.0552 (5)
C11	0.1716 (3)	0.2531 (3)	0.81658 (19)	0.0618 (5)
C12	0.1963 (3)	0.3517 (2)	0.74220 (18)	0.0627 (5)
C13	0.3606 (3)	0.4386 (3)	0.7448 (2)	0.0682 (6)
C14	0.4998 (3)	0.4288 (3)	0.8190 (2)	0.0705 (6)
C15	0.4744 (3)	0.3311 (2)	0.89346 (19)	0.0606 (5)
C16	0.0107 (3)	0.4685 (2)	0.7048 (2)	0.0607 (5)
C17	0.0689 (3)	0.5504 (3)	0.8294 (2)	0.0765 (6)
C18	0.0146 (4)	0.6599 (4)	0.8621 (3)	0.0957 (9)
C19	−0.0963 (4)	0.6846 (4)	0.7712 (4)	0.0970 (10)
C20	−0.1569 (4)	0.5991 (3)	0.6481 (3)	0.0878 (8)
C21	−0.1036 (3)	0.4910 (3)	0.6142 (2)	0.0705 (6)
H2	0.447 (3)	−0.223 (3)	1.428 (2)	0.076 (6)*
H3	0.265 (3)	−0.180 (3)	1.266 (2)	0.091 (8)*
H5	0.686 (3)	0.173 (3)	1.249 (2)	0.075 (6)*
H6	0.863 (3)	0.128 (3)	1.406 (2)	0.092 (8)*
H8	0.509 (3)	0.181 (3)	1.079 (2)	0.076 (6)*
H9	0.163 (3)	0.088 (2)	0.967 (2)	0.072 (6)*
H11	0.059 (3)	0.193 (2)	0.8184 (17)	0.056 (5)*
H14	0.604 (3)	0.488 (3)	0.819 (2)	0.088 (8)*
H15	0.572 (3)	0.323 (2)	0.948 (2)	0.065 (6)*
H17	0.135 (3)	0.531 (3)	0.888 (2)	0.077 (7)*
H18	0.052 (3)	0.708 (3)	0.942 (2)	0.092 (7)*
H19	−0.125 (4)	0.756 (4)	0.797 (3)	0.128 (12)*
H20	−0.236 (3)	0.623 (3)	0.584 (3)	0.103 (8)*
H21	−0.147 (3)	0.429 (3)	0.522 (2)	0.085 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0872 (4)	0.1072 (5)	0.0811 (4)	0.0635 (4)	0.0221 (3)	0.0467 (4)
F1	0.1130 (12)	0.0942 (10)	0.0880 (9)	0.0438 (9)	0.0304 (9)	0.0518 (8)
O1	0.0515 (8)	0.1122 (13)	0.0771 (10)	0.0305 (9)	0.0161 (7)	0.0452 (10)
O2	0.0868 (11)	0.0832 (10)	0.0580 (8)	0.0536 (9)	0.0029 (8)	0.0165 (8)
C1	0.0666 (12)	0.0679 (12)	0.0554 (10)	0.0431 (11)	0.0202 (9)	0.0225 (10)
C2	0.0680 (13)	0.0677 (13)	0.0669 (12)	0.0346 (11)	0.0275 (11)	0.0316 (11)
C3	0.0575 (12)	0.0692 (13)	0.0636 (12)	0.0297 (11)	0.0217 (10)	0.0246 (10)
C4	0.0564 (11)	0.0569 (11)	0.0519 (10)	0.0307 (9)	0.0201 (9)	0.0172 (9)
C5	0.0557 (11)	0.0660 (12)	0.0695 (13)	0.0305 (10)	0.0203 (10)	0.0315 (11)
C6	0.0538 (12)	0.0752 (14)	0.0752 (14)	0.0339 (11)	0.0182 (11)	0.0310 (12)
C7	0.0538 (11)	0.0677 (12)	0.0538 (11)	0.0296 (10)	0.0166 (9)	0.0178 (9)
C8	0.0546 (11)	0.0681 (12)	0.0593 (11)	0.0320 (10)	0.0179 (9)	0.0243 (10)
C9	0.0532 (11)	0.0677 (12)	0.0559 (11)	0.0299 (10)	0.0141 (9)	0.0177 (10)
C10	0.0554 (11)	0.0615 (11)	0.0479 (10)	0.0304 (9)	0.0124 (8)	0.0145 (9)
C11	0.0565 (12)	0.0713 (13)	0.0571 (11)	0.0332 (11)	0.0130 (10)	0.0192 (10)
C12	0.0710 (13)	0.0662 (12)	0.0517 (10)	0.0391 (11)	0.0110 (10)	0.0165 (9)
C13	0.0841 (15)	0.0640 (12)	0.0573 (11)	0.0348 (12)	0.0226 (11)	0.0224 (10)
C14	0.0643 (13)	0.0741 (14)	0.0680 (13)	0.0268 (12)	0.0234 (12)	0.0225 (12)
C15	0.0578 (11)	0.0710 (13)	0.0548 (11)	0.0342 (11)	0.0159 (9)	0.0171 (10)
C16	0.0583 (11)	0.0582 (11)	0.0666 (12)	0.0261 (10)	0.0206 (10)	0.0256 (10)
C17	0.0677 (14)	0.0768 (15)	0.0739 (15)	0.0318 (13)	0.0146 (12)	0.0157 (13)
C18	0.0834 (19)	0.0863 (19)	0.100 (2)	0.0303 (16)	0.0363 (17)	0.0018 (17)
C19	0.0878 (19)	0.0827 (18)	0.150 (3)	0.0516 (16)	0.061 (2)	0.044 (2)
C20	0.0915 (18)	0.0954 (19)	0.115 (2)	0.0592 (16)	0.0523 (17)	0.0593 (18)
C21	0.0739 (14)	0.0800 (15)	0.0762 (15)	0.0424 (12)	0.0311 (12)	0.0445 (13)

Geometric parameters (Å, º)

Cl1—C1	1.739 (2)	C12—C11	1.380 (3)
C4—C5	1.392 (3)	C11—H11	0.96 (2)
C4—C3	1.395 (3)	C2—H2	0.98 (3)
C4—C7	1.493 (3)	C5—H5	0.96 (2)
C8—C9	1.328 (3)	C16—C17	1.371 (3)
C8—C7	1.471 (3)	C16—C21	1.381 (3)
C8—H8	0.95 (2)	C15—C14	1.374 (3)
C10—C15	1.391 (3)	C15—H15	0.99 (2)
C10—C11	1.399 (3)	C14—C13	1.377 (3)
C10—C9	1.454 (3)	C14—H14	0.89 (3)
O2—C12	1.389 (2)	C21—C20	1.376 (3)
O2—C16	1.391 (2)	C21—H21	1.02 (2)
O1—C7	1.227 (2)	C17—C18	1.390 (4)
C1—C2	1.371 (3)	C17—H17	0.88 (2)
C1—C6	1.377 (3)	C13—F1	1.352 (3)
C6—C5	1.387 (3)	C20—C19	1.363 (5)
C6—H6	0.95 (3)	C20—H20	1.01 (3)
C3—C2	1.379 (3)	C18—C19	1.376 (5)
C3—H3	0.96 (3)	C18—H18	0.87 (2)
C9—H9	0.92 (2)	C19—H19	0.88 (3)
C12—C13	1.374 (3)
C5—C4—C3	118.09 (18)	C1—C2—H2	120.1 (13)
C5—C4—C7	123.88 (18)	C3—C2—H2	120.8 (14)
C3—C4—C7	118.03 (18)	C6—C5—C4	120.9 (2)
C9—C8—C7	120.7 (2)	C6—C5—H5	116.7 (14)
C9—C8—H8	118.7 (15)	C4—C5—H5	122.3 (14)
C7—C8—H8	120.5 (14)	C17—C16—C21	120.6 (2)
C15—C10—C11	118.2 (2)	C17—C16—O2	123.8 (2)
C15—C10—C9	123.31 (18)	C21—C16—O2	115.53 (19)
C11—C10—C9	118.50 (19)	C14—C15—C10	121.0 (2)
C12—O2—C16	117.69 (15)	C14—C15—H15	120.7 (13)
O1—C7—C8	119.80 (18)	C10—C15—H15	118.3 (13)
O1—C7—C4	119.35 (18)	C15—C14—C13	119.3 (2)
C8—C7—C4	120.85 (17)	C15—C14—H14	121.8 (17)
C2—C1—C6	121.57 (19)	C13—C14—H14	118.8 (17)
C2—C1—Cl1	118.99 (17)	C20—C21—C16	120.0 (3)
C6—C1—Cl1	119.42 (17)	C20—C21—H21	119.9 (14)
C1—C6—C5	119.0 (2)	C16—C21—H21	120.1 (14)
C1—C6—H6	119.8 (16)	C16—C17—C18	118.6 (3)
C5—C6—H6	121.2 (17)	C16—C17—H17	120.8 (15)
C2—C3—C4	121.3 (2)	C18—C17—H17	120.6 (15)
C2—C3—H3	120.2 (16)	F1—C13—C12	118.8 (2)
C4—C3—H3	118.5 (16)	F1—C13—C14	119.7 (2)
C8—C9—C10	129.2 (2)	C12—C13—C14	121.6 (2)
C8—C9—H9	115.9 (15)	C19—C20—C21	120.0 (3)
C10—C9—H9	114.9 (14)	C19—C20—H20	117.3 (15)
C13—C12—C11	118.77 (19)	C21—C20—H20	122.6 (15)
C13—C12—O2	120.2 (2)	C19—C18—C17	120.6 (3)
C11—C12—O2	120.9 (2)	C19—C18—H18	123.4 (16)
C12—C11—C10	121.1 (2)	C17—C18—H18	115.9 (16)
C12—C11—H11	120.8 (12)	C20—C19—C18	120.1 (3)
C10—C11—H11	118.0 (12)	C20—C19—H19	123 (2)
C1—C2—C3	119.1 (2)	C18—C19—H19	117 (2)
C9—C8—C7—O1	−2.3 (3)	C1—C6—C5—C4	1.2 (3)
C9—C8—C7—C4	177.57 (17)	C3—C4—C5—C6	−1.1 (3)
C5—C4—C7—O1	−169.50 (19)	C7—C4—C5—C6	178.41 (18)
C3—C4—C7—O1	10.0 (3)	C12—O2—C16—C17	−14.0 (3)
C5—C4—C7—C8	10.7 (3)	C12—O2—C16—C21	167.34 (19)
C3—C4—C7—C8	−169.80 (18)	C11—C10—C15—C14	1.4 (3)
C2—C1—C6—C5	−0.8 (3)	C9—C10—C15—C14	−176.51 (19)
Cl1—C1—C6—C5	−179.30 (15)	C10—C15—C14—C13	−0.1 (3)
C5—C4—C3—C2	0.7 (3)	C17—C16—C21—C20	1.6 (3)
C7—C4—C3—C2	−178.81 (18)	O2—C16—C21—C20	−179.7 (2)
C7—C8—C9—C10	177.47 (18)	C21—C16—C17—C18	−1.9 (4)
C15—C10—C9—C8	5.3 (3)	O2—C16—C17—C18	179.4 (2)
C11—C10—C9—C8	−172.6 (2)	C11—C12—C13—F1	−179.31 (18)
C16—O2—C12—C13	−89.9 (2)	O2—C12—C13—F1	4.3 (3)
C16—O2—C12—C11	93.7 (2)	C11—C12—C13—C14	0.3 (3)
C13—C12—C11—C10	1.0 (3)	O2—C12—C13—C14	−176.14 (18)
O2—C12—C11—C10	177.40 (16)	C15—C14—C13—F1	178.88 (19)
C15—C10—C11—C12	−1.8 (3)	C15—C14—C13—C12	−0.7 (3)
C9—C10—C11—C12	176.17 (18)	C16—C21—C20—C19	0.3 (4)
C6—C1—C2—C3	0.5 (3)	C16—C17—C18—C19	0.5 (4)
Cl1—C1—C2—C3	178.94 (15)	C21—C20—C19—C18	−1.7 (4)
C4—C3—C2—C1	−0.4 (3)	C17—C18—C19—C20	1.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1^i	0.96 (2)	2.35 (2)	3.285 (3)	165 (2)
C18—H18···O1^ii	0.87 (2)	2.59 (2)	3.381 (4)	151 (2)
C5—H5···Cg3^iii	0.96 (2)	3.13 (3)	3.940 (4)	144 (2)

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

(IV) (2E)-3-(2-fluoro-4-phenoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one

Crystal data

C22H17FO2	Z = 2
Mr = 332.36	F(000) = 348
Triclinic, P1	Dx = 1.257 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.196 (5) Å	Cell parameters from 795 reflections
b = 9.726 (5) Å	θ = 1.7–26.4°
c = 11.554 (7) Å	µ = 0.09 mm^−1
α = 98.887 (9)°	T = 290 K
β = 104.304 (9)°	Block, colorless
γ = 113.754 (8)°	0.24 × 0.14 × 0.12 mm
V = 878.2 (9) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3476 independent reflections
Radiation source: fine-focus sealed tube	2575 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ϕ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.940, Tmax = 0.990	k = −12→12
9092 measured reflections	l = −14→13

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) = 0.124	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0597P)^2 + 0.0991P] where P = (Fo^2 + 2Fc^2)/3
3476 reflections	(Δ/σ)max < 0.001
294 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.16 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
O1	0.17659 (14)	−0.04092 (16)	1.13449 (11)	0.0907 (4)
O2	0.06739 (15)	0.36096 (14)	0.66600 (10)	0.0844 (4)
F1	0.38959 (15)	0.53565 (13)	0.67279 (10)	0.1047 (4)
C1	0.6681 (2)	−0.05428 (18)	1.42690 (14)	0.0668 (4)
C2	0.4938 (2)	−0.1431 (2)	1.38939 (16)	0.0728 (4)
C3	0.3865 (2)	−0.11751 (19)	1.29901 (15)	0.0685 (4)
C4	0.45019 (17)	−0.00169 (16)	1.24141 (13)	0.0590 (4)
C5	0.6250 (2)	0.08632 (19)	1.27797 (16)	0.0695 (4)
C6	0.7315 (2)	0.0602 (2)	1.36934 (16)	0.0740 (4)
C7	0.32788 (19)	0.02334 (18)	1.14699 (14)	0.0640 (4)
C8	0.3861 (2)	0.12508 (18)	1.06832 (14)	0.0649 (4)
C9	0.2770 (2)	0.14442 (19)	0.98197 (14)	0.0648 (4)
C10	0.31118 (18)	0.24397 (16)	0.89912 (13)	0.0602 (4)
C11	0.1763 (2)	0.25677 (19)	0.82261 (14)	0.0661 (4)
C12	0.2026 (2)	0.35441 (19)	0.74715 (14)	0.0676 (4)
C13	0.3648 (2)	0.43956 (19)	0.74719 (15)	0.0730 (4)
C14	0.4997 (2)	0.4273 (2)	0.81945 (16)	0.0739 (4)
C15	0.4725 (2)	0.32965 (18)	0.89480 (14)	0.0655 (4)
C16	0.01872 (19)	0.47103 (18)	0.70882 (15)	0.0667 (4)
C17	0.0755 (2)	0.5551 (2)	0.83148 (18)	0.0822 (5)
C18	0.0179 (3)	0.6631 (3)	0.8624 (3)	0.1039 (7)
C19	−0.0937 (3)	0.6838 (3)	0.7718 (3)	0.1062 (7)
C20	−0.1520 (3)	0.5954 (3)	0.6516 (3)	0.0987 (6)
C21	−0.0965 (2)	0.4896 (2)	0.61837 (19)	0.0798 (5)
C22	0.7837 (3)	−0.0820 (3)	1.5274 (2)	0.0892 (6)
H2	0.446 (2)	−0.224 (2)	1.4274 (15)	0.080 (5)*
H3	0.267 (2)	−0.176 (2)	1.2749 (16)	0.088 (5)*
H5	0.673 (2)	0.164 (2)	1.2396 (15)	0.077 (5)*
H6	0.850 (2)	0.121 (2)	1.3957 (16)	0.085 (5)*
H8	0.505 (2)	0.177 (2)	1.0836 (15)	0.081 (5)*
H9	0.160 (2)	0.0865 (19)	0.9748 (15)	0.077 (5)*
H11	0.066 (2)	0.1988 (19)	0.8246 (15)	0.075 (5)*
H14	0.606 (2)	0.486 (2)	0.8163 (15)	0.085 (5)*
H15	0.570 (2)	0.3187 (17)	0.9463 (14)	0.072 (4)*
H17	0.152 (2)	0.536 (2)	0.8917 (17)	0.087 (5)*
H18	0.057 (3)	0.708 (3)	0.945 (2)	0.106 (7)*
H19	−0.128 (3)	0.761 (3)	0.798 (2)	0.131 (8)*
H20	−0.243 (3)	0.606 (3)	0.583 (2)	0.132 (8)*
H21	−0.132 (3)	0.427 (2)	0.529 (2)	0.111 (7)*
H22B	0.825 (3)	−0.147 (3)	1.492 (2)	0.126 (8)*
H22C	0.732 (4)	−0.121 (4)	1.584 (3)	0.163 (11)*
H22A	0.892 (4)	0.017 (4)	1.578 (3)	0.168 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1226 (9)	0.0997 (8)	0.0924 (7)	0.0449 (7)	0.0355 (6)	0.0487 (6)
O1	0.0575 (7)	0.1212 (10)	0.0891 (8)	0.0324 (7)	0.0223 (6)	0.0475 (7)
O2	0.0951 (8)	0.0934 (8)	0.0635 (7)	0.0574 (7)	0.0064 (6)	0.0140 (6)
C1	0.0781 (10)	0.0719 (9)	0.0616 (8)	0.0452 (8)	0.0234 (7)	0.0190 (7)
C2	0.0841 (11)	0.0712 (10)	0.0738 (10)	0.0378 (9)	0.0347 (9)	0.0311 (8)
C3	0.0634 (9)	0.0693 (9)	0.0703 (9)	0.0271 (8)	0.0247 (8)	0.0204 (8)
C4	0.0607 (8)	0.0585 (8)	0.0588 (8)	0.0280 (7)	0.0223 (7)	0.0147 (6)
C5	0.0619 (9)	0.0702 (9)	0.0776 (10)	0.0288 (8)	0.0225 (8)	0.0309 (8)
C6	0.0584 (9)	0.0788 (10)	0.0828 (11)	0.0319 (8)	0.0180 (8)	0.0270 (9)
C7	0.0578 (8)	0.0696 (9)	0.0613 (8)	0.0282 (7)	0.0186 (7)	0.0157 (7)
C8	0.0578 (9)	0.0709 (9)	0.0656 (9)	0.0293 (7)	0.0200 (7)	0.0211 (7)
C9	0.0573 (8)	0.0700 (9)	0.0617 (9)	0.0277 (7)	0.0164 (7)	0.0156 (7)
C10	0.0601 (8)	0.0636 (8)	0.0538 (8)	0.0303 (7)	0.0149 (6)	0.0108 (6)
C11	0.0591 (9)	0.0718 (9)	0.0609 (9)	0.0298 (8)	0.0145 (7)	0.0131 (7)
C12	0.0741 (10)	0.0703 (9)	0.0551 (8)	0.0384 (8)	0.0117 (7)	0.0118 (7)
C13	0.0891 (12)	0.0676 (9)	0.0607 (9)	0.0353 (9)	0.0237 (8)	0.0197 (7)
C14	0.0684 (10)	0.0747 (10)	0.0717 (10)	0.0258 (8)	0.0262 (8)	0.0193 (8)
C15	0.0597 (9)	0.0725 (9)	0.0612 (8)	0.0319 (7)	0.0167 (7)	0.0133 (7)
C16	0.0649 (9)	0.0627 (8)	0.0750 (10)	0.0274 (7)	0.0264 (8)	0.0280 (8)
C17	0.0717 (11)	0.0789 (11)	0.0830 (12)	0.0313 (9)	0.0186 (9)	0.0110 (9)
C18	0.0907 (14)	0.0889 (14)	0.1131 (18)	0.0313 (12)	0.0391 (14)	0.0006 (13)
C19	0.0940 (15)	0.0881 (14)	0.163 (3)	0.0530 (12)	0.0619 (17)	0.0446 (16)
C20	0.1047 (15)	0.1044 (15)	0.1260 (19)	0.0640 (13)	0.0566 (14)	0.0633 (15)
C21	0.0844 (11)	0.0912 (12)	0.0853 (12)	0.0470 (10)	0.0377 (10)	0.0494 (10)
C22	0.1021 (15)	0.1061 (15)	0.0815 (13)	0.0665 (14)	0.0288 (12)	0.0366 (12)

Geometric parameters (Å, º)

C10—C15	1.397 (2)	C1—C2	1.389 (2)
C10—C11	1.397 (2)	C1—C22	1.507 (2)
C10—C9	1.464 (2)	C5—C6	1.383 (2)
C4—C5	1.392 (2)	C5—H5	0.945 (17)
C4—C3	1.395 (2)	F1—C13	1.356 (2)
C4—C7	1.487 (2)	C16—C17	1.372 (2)
O2—C16	1.387 (2)	C16—C21	1.383 (2)
O2—C12	1.3911 (19)	C6—H6	0.946 (19)
C11—C12	1.377 (2)	C2—H2	0.962 (18)
C11—H11	0.951 (18)	C15—H15	1.001 (16)
C8—C9	1.324 (2)	C21—C20	1.366 (3)
C8—C7	1.478 (2)	C21—H21	1.01 (2)
C8—H8	0.954 (18)	C22—H22B	0.95 (3)
C9—H9	0.964 (18)	C22—H22C	0.94 (3)
C7—O1	1.2326 (19)	C22—H22A	1.01 (3)
C3—C2	1.376 (2)	C17—C18	1.392 (3)
C3—H3	0.949 (19)	C17—H17	0.954 (18)
C12—C13	1.384 (3)	C18—C19	1.375 (4)
C14—C13	1.374 (3)	C18—H18	0.89 (2)
C14—C15	1.376 (2)	C20—C19	1.359 (4)
C14—H14	0.925 (18)	C20—H20	1.05 (2)
C1—C6	1.385 (2)	C19—H19	0.96 (3)
C15—C10—C11	118.34 (15)	C17—C16—O2	123.88 (15)
C15—C10—C9	123.30 (13)	C21—C16—O2	115.07 (15)
C11—C10—C9	118.34 (14)	C5—C6—C1	121.19 (16)
C5—C4—C3	117.94 (14)	C5—C6—H6	121.2 (11)
C5—C4—C7	123.77 (14)	C1—C6—H6	117.6 (11)
C3—C4—C7	118.27 (14)	C3—C2—C1	121.35 (16)
C16—O2—C12	118.04 (12)	C3—C2—H2	118.7 (10)
C12—C11—C10	120.77 (16)	C1—C2—H2	120.0 (10)
C12—C11—H11	120.1 (10)	C14—C15—C10	121.20 (15)
C10—C11—H11	119.1 (10)	C14—C15—H15	119.2 (9)
C9—C8—C7	120.75 (15)	C10—C15—H15	119.6 (9)
C9—C8—H8	122.1 (10)	F1—C13—C14	119.67 (16)
C7—C8—H8	117.1 (10)	F1—C13—C12	118.79 (16)
C8—C9—C10	128.49 (15)	C14—C13—C12	121.54 (16)
C8—C9—H9	114.8 (10)	C20—C21—C16	119.4 (2)
C10—C9—H9	116.7 (10)	C20—C21—H21	122.7 (12)
O1—C7—C8	119.68 (14)	C16—C21—H21	117.9 (12)
O1—C7—C4	119.71 (14)	C1—C22—H22B	110.5 (14)
C8—C7—C4	120.61 (13)	C1—C22—H22C	111.6 (18)
C2—C3—C4	120.79 (16)	H22B—C22—H22C	113 (2)
C2—C3—H3	121.3 (11)	C1—C22—H22A	112.6 (17)
C4—C3—H3	117.9 (11)	H22B—C22—H22A	102 (2)
C11—C12—C13	119.15 (15)	H22C—C22—H22A	107 (2)
C11—C12—O2	120.83 (15)	C16—C17—C18	118.3 (2)
C13—C12—O2	119.90 (15)	C16—C17—H17	118.6 (11)
C13—C14—C15	118.97 (17)	C18—C17—H17	123.0 (11)
C13—C14—H14	118.9 (11)	C19—C18—C17	120.5 (2)
C15—C14—H14	122.2 (11)	C19—C18—H18	127.2 (14)
C6—C1—C2	117.94 (15)	C17—C18—H18	112.2 (14)
C6—C1—C22	121.38 (18)	C19—C20—C21	120.8 (2)
C2—C1—C22	120.69 (17)	C19—C20—H20	120.4 (13)
C6—C5—C4	120.79 (16)	C21—C20—H20	118.8 (13)
C6—C5—H5	118.8 (10)	C20—C19—C18	120.0 (2)
C4—C5—H5	120.4 (10)	C20—C19—H19	122.8 (15)
C17—C16—C21	121.04 (17)	C18—C19—H19	117.2 (15)
C15—C10—C11—C12	−1.6 (2)	C2—C1—C6—C5	0.5 (2)
C9—C10—C11—C12	176.97 (13)	C22—C1—C6—C5	−179.35 (17)
C7—C8—C9—C10	177.56 (13)	C4—C3—C2—C1	0.5 (2)
C15—C10—C9—C8	4.3 (2)	C6—C1—C2—C3	−0.8 (2)
C11—C10—C9—C8	−174.20 (15)	C22—C1—C2—C3	179.02 (17)
C9—C8—C7—O1	−2.0 (2)	C13—C14—C15—C10	−0.2 (2)
C9—C8—C7—C4	178.26 (13)	C11—C10—C15—C14	1.5 (2)
C5—C4—C7—O1	−168.08 (15)	C9—C10—C15—C14	−176.99 (14)
C3—C4—C7—O1	10.4 (2)	C15—C14—C13—F1	179.79 (14)
C5—C4—C7—C8	11.7 (2)	C15—C14—C13—C12	−1.0 (2)
C3—C4—C7—C8	−169.90 (13)	C11—C12—C13—F1	−179.89 (13)
C5—C4—C3—C2	0.2 (2)	O2—C12—C13—F1	4.0 (2)
C7—C4—C3—C2	−178.31 (14)	C11—C12—C13—C14	0.9 (2)
C10—C11—C12—C13	0.4 (2)	O2—C12—C13—C14	−175.24 (14)
C10—C11—C12—O2	176.52 (12)	C17—C16—C21—C20	1.2 (3)
C16—O2—C12—C11	91.19 (18)	O2—C16—C21—C20	180.00 (16)
C16—O2—C12—C13	−92.74 (18)	C21—C16—C17—C18	−1.8 (3)
C3—C4—C5—C6	−0.5 (2)	O2—C16—C17—C18	179.55 (16)
C7—C4—C5—C6	177.89 (14)	C16—C17—C18—C19	0.3 (3)
C12—O2—C16—C17	−11.6 (2)	C16—C21—C20—C19	0.9 (3)
C12—O2—C16—C21	169.66 (14)	C21—C20—C19—C18	−2.4 (3)
C4—C5—C6—C1	0.2 (3)	C17—C18—C19—C20	1.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1^i	0.95 (2)	2.35 (2)	3.288 (3)	167 (2)
C18—H18···O1^ii	0.89 (2)	2.64 (2)	3.443 (3)	150 (2)
C5—H5···Cg3^iii	0.95 (2)	3.21 (2)	3.980 (3)	140 (1)

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

(V) (2E)-3-(2-fluoro-4-phenoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

Crystal data

C22H17FO3	Z = 2
Mr = 348.36	F(000) = 364
Triclinic, P1	Dx = 1.349 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.645 (4) Å	Cell parameters from 856 reflections
b = 10.111 (5) Å	θ = 1.4–25.6°
c = 10.537 (6) Å	µ = 0.10 mm^−1
α = 66.706 (7)°	T = 290 K
β = 65.347 (8)°	Block, colorless
γ = 80.949 (9)°	0.12 × 0.08 × 0.04 mm
V = 857.8 (7) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3419 independent reflections
Radiation source: fine-focus sealed tube	2219 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ϕ and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.946, Tmax = 0.996	k = −12→12
8983 measured reflections	l = −12→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0405P)^2 + 0.1909P] where P = (Fo^2 + 2Fc^2)/3
3419 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.17 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	0.55831 (16)	0.45569 (13)	0.61429 (15)	0.0661 (4)
O1	0.88328 (18)	−0.31997 (16)	0.49310 (17)	0.0648 (5)
O2	0.35389 (16)	0.24070 (16)	0.71921 (16)	0.0522 (4)
O3	1.35658 (17)	−0.23643 (16)	−0.17089 (16)	0.0572 (4)
C1	1.2618 (2)	−0.2390 (2)	−0.0307 (2)	0.0434 (5)
C2	1.2244 (3)	−0.3601 (2)	0.1001 (3)	0.0465 (6)
C3	1.1244 (2)	−0.3490 (2)	0.2347 (3)	0.0453 (5)
C4	1.0616 (2)	−0.2182 (2)	0.2431 (2)	0.0409 (5)
C5	1.1055 (3)	−0.0975 (2)	0.1111 (2)	0.0475 (6)
C6	1.2031 (3)	−0.1078 (2)	−0.0237 (3)	0.0503 (6)
C7	0.9440 (2)	−0.2112 (2)	0.3868 (2)	0.0456 (5)
C8	0.9002 (3)	−0.0681 (2)	0.3980 (2)	0.0476 (6)
C9	0.7648 (3)	−0.0433 (2)	0.4905 (2)	0.0449 (5)
C10	0.7117 (2)	0.0919 (2)	0.5157 (2)	0.0402 (5)
C11	0.5588 (2)	0.1042 (2)	0.6053 (2)	0.0429 (5)
C12	0.5074 (2)	0.2269 (2)	0.6367 (2)	0.0431 (5)
C13	0.6086 (3)	0.3375 (2)	0.5792 (2)	0.0465 (5)
C14	0.7590 (3)	0.3300 (3)	0.4895 (2)	0.0502 (6)
C15	0.8094 (3)	0.2067 (2)	0.4584 (2)	0.0473 (6)
C16	0.3127 (2)	0.2483 (2)	0.8594 (2)	0.0408 (5)
C17	0.4031 (3)	0.1986 (3)	0.9399 (3)	0.0516 (6)
C18	0.3492 (3)	0.2045 (3)	1.0820 (3)	0.0570 (6)
C19	0.2081 (3)	0.2603 (3)	1.1407 (3)	0.0558 (6)
C20	0.1193 (3)	0.3092 (3)	1.0585 (3)	0.0531 (6)
C21	0.1705 (2)	0.3037 (2)	0.9175 (2)	0.0468 (5)
C22	1.4148 (4)	−0.3683 (3)	−0.1905 (4)	0.0729 (9)
H2	1.263 (2)	−0.448 (2)	0.098 (2)	0.057 (7)*
H3	1.101 (2)	−0.430 (2)	0.324 (2)	0.041 (6)*
H5	1.066 (2)	−0.005 (2)	0.112 (2)	0.048 (6)*
H6	1.231 (2)	−0.028 (2)	−0.116 (2)	0.048 (6)*
H8	0.976 (2)	0.009 (2)	0.335 (2)	0.056 (6)*
H9	0.690 (2)	−0.124 (2)	0.550 (2)	0.051 (6)*
H11	0.491 (2)	0.029 (2)	0.644 (2)	0.042 (6)*
H13	0.828 (2)	0.410 (2)	0.452 (2)	0.059 (7)*
H15	0.915 (2)	0.197 (2)	0.402 (2)	0.047 (6)*
H17	0.500 (3)	0.161 (2)	0.900 (2)	0.060 (7)*
H18	0.415 (3)	0.170 (2)	1.138 (2)	0.064 (7)*
H19	0.174 (2)	0.266 (2)	1.239 (2)	0.058 (6)*
H20	0.020 (3)	0.348 (2)	1.101 (2)	0.062 (7)*
H21	0.111 (2)	0.338 (2)	0.855 (2)	0.057 (6)*
H22B	1.477 (3)	−0.417 (3)	−0.126 (3)	0.094 (10)*
H22A	1.483 (3)	−0.342 (3)	−0.297 (3)	0.088 (9)*
H22C	1.334 (3)	−0.435 (3)	−0.152 (3)	0.095 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0788 (10)	0.0545 (8)	0.0730 (9)	0.0132 (7)	−0.0261 (8)	−0.0399 (7)
O1	0.0685 (11)	0.0447 (9)	0.0529 (10)	0.0022 (8)	−0.0064 (8)	−0.0094 (8)
O2	0.0407 (9)	0.0750 (11)	0.0526 (9)	0.0137 (7)	−0.0192 (7)	−0.0390 (8)
O3	0.0643 (11)	0.0535 (10)	0.0523 (9)	0.0050 (8)	−0.0116 (8)	−0.0317 (8)
C1	0.0411 (12)	0.0469 (13)	0.0498 (13)	0.0021 (10)	−0.0165 (10)	−0.0272 (11)
C2	0.0492 (14)	0.0366 (13)	0.0584 (15)	0.0099 (10)	−0.0220 (11)	−0.0246 (11)
C3	0.0496 (13)	0.0365 (12)	0.0474 (13)	0.0031 (10)	−0.0193 (11)	−0.0138 (11)
C4	0.0418 (12)	0.0381 (12)	0.0447 (12)	0.0064 (9)	−0.0169 (10)	−0.0194 (10)
C5	0.0556 (14)	0.0334 (12)	0.0520 (14)	0.0102 (10)	−0.0173 (11)	−0.0218 (11)
C6	0.0597 (15)	0.0381 (13)	0.0440 (13)	0.0011 (11)	−0.0123 (11)	−0.0150 (11)
C7	0.0458 (13)	0.0438 (13)	0.0466 (13)	0.0061 (10)	−0.0179 (11)	−0.0182 (11)
C8	0.0486 (14)	0.0457 (14)	0.0414 (12)	0.0037 (11)	−0.0079 (11)	−0.0205 (11)
C9	0.0486 (14)	0.0429 (13)	0.0403 (12)	0.0029 (11)	−0.0151 (11)	−0.0157 (10)
C10	0.0424 (12)	0.0426 (12)	0.0339 (11)	0.0056 (10)	−0.0127 (9)	−0.0166 (9)
C11	0.0429 (13)	0.0483 (13)	0.0378 (11)	0.0001 (11)	−0.0138 (10)	−0.0181 (10)
C12	0.0398 (12)	0.0556 (14)	0.0390 (11)	0.0104 (11)	−0.0164 (10)	−0.0250 (11)
C13	0.0572 (15)	0.0440 (13)	0.0460 (12)	0.0109 (11)	−0.0228 (11)	−0.0253 (10)
C14	0.0538 (15)	0.0492 (14)	0.0462 (13)	−0.0035 (12)	−0.0141 (11)	−0.0206 (11)
C15	0.0391 (13)	0.0552 (14)	0.0421 (12)	0.0019 (11)	−0.0067 (10)	−0.0229 (11)
C16	0.0401 (12)	0.0432 (12)	0.0407 (11)	0.0034 (10)	−0.0131 (10)	−0.0210 (10)
C17	0.0407 (13)	0.0623 (15)	0.0517 (14)	0.0092 (11)	−0.0168 (11)	−0.0253 (12)
C18	0.0520 (15)	0.0731 (17)	0.0453 (14)	−0.0053 (13)	−0.0193 (12)	−0.0185 (12)
C19	0.0537 (16)	0.0668 (16)	0.0401 (13)	−0.0136 (12)	−0.0054 (12)	−0.0216 (12)
C20	0.0422 (14)	0.0568 (15)	0.0522 (14)	0.0029 (11)	−0.0051 (12)	−0.0272 (12)
C21	0.0390 (13)	0.0517 (14)	0.0515 (14)	0.0048 (10)	−0.0166 (11)	−0.0235 (11)
C22	0.085 (2)	0.0600 (18)	0.069 (2)	0.0038 (17)	−0.0081 (18)	−0.0444 (17)

Geometric parameters (Å, º)

F1—C13	1.348 (2)	C9—C8	1.321 (3)
C3—C2	1.381 (3)	C9—H9	0.99 (2)
C3—C4	1.385 (3)	C15—H15	0.96 (2)
C3—H3	0.937 (19)	C2—H2	0.92 (2)
O2—C12	1.387 (2)	C8—H8	0.97 (2)
O2—C16	1.392 (2)	C5—C6	1.373 (3)
O3—C1	1.367 (2)	C5—H5	0.95 (2)
O3—C22	1.422 (3)	C6—H6	0.95 (2)
C10—C15	1.383 (3)	C16—C17	1.370 (3)
C10—C11	1.399 (3)	C16—C21	1.377 (3)
C10—C9	1.468 (3)	C21—C20	1.379 (3)
C11—C12	1.374 (3)	C21—H21	0.97 (2)
C11—H11	0.93 (2)	C17—C18	1.388 (3)
O1—C7	1.220 (2)	C17—H17	0.94 (2)
C4—C5	1.390 (3)	C18—C19	1.373 (3)
C4—C7	1.487 (3)	C18—H18	0.97 (2)
C12—C13	1.373 (3)	C20—C19	1.369 (3)
C14—C13	1.372 (3)	C20—H20	0.97 (2)
C14—C15	1.378 (3)	C22—H22B	1.02 (3)
C14—H13	0.98 (2)	C22—H22A	0.99 (3)
C1—C6	1.376 (3)	C22—H22C	0.95 (3)
C1—C2	1.385 (3)	C19—H19	0.97 (2)
C7—C8	1.479 (3)
C2—C3—C4	121.5 (2)	C3—C2—H2	119.7 (13)
C2—C3—H3	120.3 (11)	C1—C2—H2	120.5 (13)
C4—C3—H3	118.2 (11)	C9—C8—C7	122.4 (2)
C12—O2—C16	118.08 (15)	C9—C8—H8	120.4 (12)
C1—O3—C22	119.1 (2)	C7—C8—H8	117.2 (12)
C15—C10—C11	118.4 (2)	C6—C5—C4	121.4 (2)
C15—C10—C9	122.2 (2)	C6—C5—H5	118.2 (12)
C11—C10—C9	119.4 (2)	C4—C5—H5	120.4 (12)
C12—C11—C10	120.7 (2)	C5—C6—C1	120.3 (2)
C12—C11—H11	119.4 (12)	C5—C6—H6	123.1 (12)
C10—C11—H11	119.9 (12)	C1—C6—H6	116.6 (12)
C3—C4—C5	117.5 (2)	C17—C16—C21	121.0 (2)
C3—C4—C7	120.35 (19)	C17—C16—O2	123.03 (18)
C5—C4—C7	121.99 (18)	C21—C16—O2	115.96 (18)
C13—C12—C11	119.1 (2)	C16—C21—C20	119.3 (2)
C13—C12—O2	120.80 (19)	C16—C21—H21	117.5 (12)
C11—C12—O2	120.1 (2)	C20—C21—H21	123.2 (12)
C13—C14—C15	118.6 (2)	C16—C17—C18	118.9 (2)
C13—C14—H13	119.5 (12)	C16—C17—H17	120.7 (13)
C15—C14—H13	121.9 (13)	C18—C17—H17	120.4 (13)
F1—C13—C14	119.4 (2)	C19—C18—C17	120.7 (2)
F1—C13—C12	118.68 (19)	C19—C18—H18	120.8 (13)
C14—C13—C12	121.9 (2)	C17—C18—H18	118.4 (13)
O3—C1—C6	115.17 (19)	C19—C20—C21	120.7 (2)
O3—C1—C2	125.42 (19)	C19—C20—H20	119.0 (13)
C6—C1—C2	119.4 (2)	C21—C20—H20	120.3 (13)
O1—C7—C8	120.24 (19)	O3—C22—H22B	109.1 (16)
O1—C7—C4	121.39 (19)	O3—C22—H22A	105.7 (16)
C8—C7—C4	118.36 (19)	H22B—C22—H22A	109 (2)
C8—C9—C10	127.0 (2)	O3—C22—H22C	111.0 (17)
C8—C9—H9	117.4 (12)	H22B—C22—H22C	104 (2)
C10—C9—H9	115.5 (12)	H22A—C22—H22C	118 (2)
C14—C15—C10	121.3 (2)	C20—C19—C18	119.5 (2)
C14—C15—H15	119.5 (12)	C20—C19—H19	120.9 (13)
C10—C15—H15	119.0 (12)	C18—C19—H19	119.6 (13)
C3—C2—C1	119.8 (2)
C15—C10—C11—C12	−0.6 (3)	C11—C10—C15—C14	0.8 (3)
C9—C10—C11—C12	176.89 (19)	C9—C10—C15—C14	−176.7 (2)
C2—C3—C4—C5	−1.4 (3)	C4—C3—C2—C1	−1.0 (3)
C2—C3—C4—C7	174.7 (2)	O3—C1—C2—C3	−178.6 (2)
C10—C11—C12—C13	−0.2 (3)	C6—C1—C2—C3	2.4 (3)
C10—C11—C12—O2	176.68 (17)	C10—C9—C8—C7	177.1 (2)
C16—O2—C12—C13	−68.0 (2)	O1—C7—C8—C9	−25.9 (3)
C16—O2—C12—C11	115.2 (2)	C4—C7—C8—C9	153.5 (2)
C15—C14—C13—F1	178.12 (19)	C3—C4—C5—C6	2.4 (3)
C15—C14—C13—C12	−0.8 (3)	C7—C4—C5—C6	−173.6 (2)
C11—C12—C13—F1	−178.00 (18)	C4—C5—C6—C1	−1.0 (4)
O2—C12—C13—F1	5.1 (3)	O3—C1—C6—C5	179.5 (2)
C11—C12—C13—C14	1.0 (3)	C2—C1—C6—C5	−1.4 (3)
O2—C12—C13—C14	−175.89 (19)	C12—O2—C16—C17	−21.4 (3)
C22—O3—C1—C6	−175.9 (3)	C12—O2—C16—C21	161.43 (19)
C22—O3—C1—C2	5.0 (3)	C17—C16—C21—C20	0.2 (3)
C3—C4—C7—O1	−11.3 (3)	O2—C16—C21—C20	177.45 (19)
C5—C4—C7—O1	164.5 (2)	C21—C16—C17—C18	0.1 (3)
C3—C4—C7—C8	169.3 (2)	O2—C16—C17—C18	−176.9 (2)
C5—C4—C7—C8	−14.8 (3)	C16—C17—C18—C19	−0.6 (4)
C15—C10—C9—C8	−9.8 (3)	C16—C21—C20—C19	−0.1 (3)
C11—C10—C9—C8	172.8 (2)	C21—C20—C19—C18	−0.4 (4)
C13—C14—C15—C10	0.0 (3)	C17—C18—C19—C20	0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1^i	0.94 (2)	2.53 (2)	3.427 (3)	160 (2)
C18—H18···O3^ii	0.97 (3)	2.59 (3)	3.432 (4)	145 (2)
C21—H21···Cg2^iii	0.97 (3)	2.84 (2)	3.548 (4)	130 (1)

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