Four substituted pyrazolines

In the title compounds 5-(3-fluoro-4-phenoxy­phenyl)-1,3-biphenyl-4,5-dihydro-1H-pyrazole, C₂₇H₂₁FN₂O, (I), 3-(4-chloro­phenyl)-5-(3-fluoro-4-phenoxy­phenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, C₂₇H₂₀ClFN₂O, (II), 5-(3-fluoro-4-phen­oxy­phenyl)-3-(4-methyl­phenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, C₂₈H₂₃FN₂O, (III), and 5-(3-fluoro-4-phenoxy­phenyl)-3-(4-methoxy­phenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, C₂₈H₂₃FN₂O₂, (IV), the five-membered pyrazole ring exists in an envelope conformation. The crystal structure of (I) has three independent C—H...π inter­molecular inter­actions. In (II), an inter­molecular C—Cl...π contact is present, forming mol­ecular chains. Replacement of this chloro group in (II) by a methyl group yields an isomorphic crystal structure, (III).

S1. Comment

Pyrazolines are an important class of compounds found to possess extensive physiological properties including antibacterial (Nauduri & Reddy, 1998; Azarifar & Shaabanzadeh, 2002), anti-inflammatory (Kuroda et al., 1992; Udupi, Kushnoor & Bhat, 1998; Udupi, Rao & Bhat, 1998), antifungal (Korgaokar et al., 1996), analgesic (Udupi, Kushnoor & Bhat, 1998; Udupi, Rao & Bhat, 1998),antitumour (Chen et al., 1997), antidepressant (Bilgin et al., 1993) and antiprotozoal (Cetin et al., 2003). They also possess fungicidal or herbicidal properties (Takao et al., 1994; Ohvchi & Okada, 1998; Malhotra et al., 1997), and are used as scintillation solutes and antioxidants in lubrication oils (Beher et al., 1967). Previous studies have demonstrated the monoamine oxidase (MAO) inhibitory activities of 1,3,5-triphenyl-2-pyrazolines (Soni et al., 1987; Chimenti et al., 2004). Several recent structural determinations of this class of compounds have also been carried out (Köysal et al., 2005; Langer et al., 2007).

In view of the diverse applications of this class of compounds, we report here the crystal structures of four substituted pyrazoles, namely (5S)-5-(3-fluoro-4-phenoxyphenyl)-1,3-biphenyl-4,5-dihydro-1H-pyrazole, (I), (5S)-3-(4-chlorophenyl)-5-(3-fluoro-4-phenoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, (II), (5R)-5-(3-fluoro-4-phenoxyphenyl)-3-(4-methylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, (III), and (5S)-5-(3-fluoro-4-phenoxyphenyl)-3-(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazole, (IV). The effect of varying molecular substituents on the molecular geometry, the conformational changes and the associated packing features have also been analysed. All four structures have pyrazoline (ring A), 3-fluoro-4-phenoxyphenyl (attached to C5, rings B and C), phenyl (attached to N1, ring D) and substituted phenyl (attached to C3, ring E) moieties in the molecule. The different groups present on ring E are the chloro, methyl and methoxy substituents in compounds (II)–(IV), respectively. All four compounds crystallize with one molecule in the asymmetric unit. In contrast with the unsubstituted pyrazoline, (I), which crystallizes in a noncentrosymmetric space group, the other three compounds crystallize in centrosymmetric space groups. The absolute configuration in (I) was not defined and so is shown to match the configurations shown in the other three structures.

Figs. 1–4 depict the molecular structures of the four pyrazolines with their different substitutions, with the corresponding atom-numbering schemes. In all four compounds, the central ring A exists in an envelope conformation with the chiral atom C3 (crystallographic numbering) forming the flap; deviations from the least-squares planes for (I)–(IV) are given in Table 8. The remaining atoms N1, N2, C1 and C2 of ring A are coplanar, with the out-of-plane distances being -0.0004 (2) and -0.003 (3) Å for atom N2 in (I) and (IV), respectively. The corresponding distances are 0.002 (2) and 0.005 (2) Å for atom C2 in (III) and (IV), respectively. The bond lengths and torsion angles of the five-membered ring (Tables 1, 3, 4 and 6) in all compounds are in agreement with the expected values reported in the literature (Allen et al., 1987; Allen, 2002). The N—N bond lengths of the pyrazoline ring in (I) [1.383 (2) Å] and (IV) [1.390 (3) Å] are similar. In case of (II) [1.363 (3) Å] and (III)[1.365 (2) Å], these are shorter, indicating greater double-bond character due to resonance delocalization between the lone pair of electrons on atom N1 and the C═N double bond of ring A and extending to ring E.

In all four compounds, the 3-fluoro-4-phenoxyphenyl moiety occupies a pseudo-axial position and hence is approximately perpendicular to the mean plane of the pyrazoline ring, the dihedral angle being 80.25 (6)° in (I) (Table 9). This value is comparable with that observed in 3-(4-bromophenyl)-5-(4-dimethylaminophenyl)-1-phenyl-2-pyrazoline (Langer et al., 2007),in which the 4-dimethylaminophenyl moiety makes an angle of 74.3 (1)° with the central pyrazoline ring. Similar geometric characteristics are observed in N-substituted 3,5-diphenyl-2-pyrazoline-1-thiocarboxamides (Köysal et al., 2005), where the methoxyphenyl and methylphenyl moieties make dihedral angles of 89.29 (8) and 80.39 (10)°, respectively. A similar orientation at the C5 atom is also observed in spiro compounds (Bruno et al., 2004), where the isoxazoline ring is connected to the substituted pyrazoline ring with the dihedral angle lying in the range 87.7 (1)–89.0 (1)°. In the isomorphic compounds (II) and (III), the dihedral angles between ring A and rings D and E are similar to those observed in 3-(4-bromophenyl)-5-(4-dimethylaminophenyl)-1-phenyl-2-pyrazoline (Langer et al., 2007), where rings D and E are taken as the phenyl and 4-bromo groups, respectively (Table 9). A ring-puckering analysis (Cremer & Pople, 1975) of the five-membered pyrazoline ring gives the parameters listed in Table 10.

In the absence of strong hydrogen-bond donors in the molecule, the crystal packing is controlled by the involvement of weak C—H···π intermolecular interactions (Nishio et al., 1995; Takahashi et al., 2000; Umezawa et al., 1999). The molecules in (I) are held by three different weak yet directional C—H···π interactions, involving atoms H18 and H2B with rings C and E and forming chains along the crystallographic a axis, coupled with the formation of chains along b axis involving atom H26 and ring D (see Fig. 5 and Table 2).

In the crystal structure of (II), the packing is controlled by a non-covalent C—Cl···π interaction involving the lone pair of electrons on the Cl atom with the antibonding orbitals of the phenyl ring B [C25—Cl1···Cg2 = 137.2 (1)°; Cg2 is the centroid of ring B] (Fig. 6 and Table 3). These interactions are well documented in the literature and have been extensively studied in small molecules and in proteins (Prasanna & Guru Row, 2000; Saraogi et al., 2003) using the Cambridge Structural Database (Version?; Allen, 2002). In (II), these interactions form molecular chains along the crystallographic screw b axis. Replacement of the Cl atom by a methyl group in the isomorphic structure, (III), sees the C—Cl···π interaction being replaced by a C—H···π intermolecular interaction, involving atom H28C of the methyl group and phenyl ring B (Table 5).

In compound (IV), the presence of a methoxy group results in a change in the molecular conformation around the C16—N1 bond, with the torsion angle increasing from -8.1 (3)° in the case of (III) to 35.7 (4)° in (IV). The structure is stabilized by a C—H···π intermolecular interaction, involving atom H28A and the five-membered pyrazoline ring A, forming molecular chains along the screw b axis (Fig. 7 and Table 7).

Related literature

For related literature, see: Allen (2002); Allen et al. (1987); Azarifar & Shaabanzadeh (2002); Beher et al. (1967); Bhatt et al. (2001); Bilgin et al. (1993); Bruno et al. (2004); Cetin et al. (2003); Chen et al. (1997); Chimenti et al. (2004); Cremer & Pople (1975); Dandia et al. (1993); Köysal et al. (2005); Korgaokar et al. (1996); Kuroda et al. (1992); Langer et al. (2007); Malhotra et al. (1997); Mogilaiah & Sudhakar (2003); Mohan (2006); Nauduri & Reddy (1998); Nishio et al. (1995); Ohvchi & Okada (1998); Prasanna & Guru Row (2000); Saraogi et al. (2003); Soni et al. (1987); Takahashi et al. (2000); Takao et al. (1994); Udupi, Kushnoor & Bhat (1998); Udupi, Rao & Bhat (1998); Umezawa et al. (1999).

S2. Experimental

A mixture of chalcone (with different substitutions; 0.01 mol), acetic acid (20 ml) and phenylhydrazine (0.01 mol) was refluxed for 12 h. The resulting mixture was cooled to 283 K and filtered. The progress of the reaction and the purity of the products were monitored by thin-layer chromatography. The crude products thus obtained were recrystallized from propan-2-ol (Mogilaiah & Sudhakar, 2003; Dandia et al., 1993; Bhatt et al., 2001; Mohan, 2006). All four compounds were characterized using mass, NMR and IR spectra, m. p. measurements, and elemental analyses. A small quantity of each sample was dissolved in a suitable solvent or solvent combination, such as dichloromethane, dichloromethane–hexane (Ratio?), acetonitrile, ethyl acetate or ethyl acetate–hexane (Ratio?). The crystals used for data collection were obtained from ethyl acetate–hexane (Ratio?).

S3. Refinement

Friedel-equivalent relections were averaged before refinement in (I). The H atoms of the methyl groups in (III) and (IV) were fixed in geometrical positions and allowed to ride on their parent C atoms, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C). The remaining H atoms in all four structures were located in a difference Fourier map and refined isotropically. The C—H bond lengths are in the range of 0.85 (4)–1.03 (3) Å.

Computing details

For all compounds, data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. A view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. A view of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 4. A view of (IV), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 5. A partial packing diagram for (I), depicting the formation of C—H···π interactions (dotted lines) with respect to the reference molecule at (x, y, z). Cg3, Cg4 and Cg5 are the centroids of rings C, D and E, respectively. Molecules labelled with the suffixes # or * are at the symmetry positions (x + 1, y, z) and (-x + 1, y + 1/2, - z + 1), respectively.
	Fig. 6. A partial packing diagram for (II), depicting C—Cl···π intermolecular contacts (dotted lines) along the b axis. Cg2 is the centroid of ring B. The suffix # indicates the symmetry-related molecule at (-x, y - 1/2, -z + 3/2).
	Fig. 7. A partial packing diagram for (IV), highlighting the C—H···π contact (dotted lines) along the b axis. Cg1 is the centroid of the five-membered pyrazoline ring. The suffix # depicts the symmetry-related molecule at (-x + 2,y - 1/2, -z + 1/2).

(I) (5S)-5-(3-fluoro-4-phenoxyphenyl)-1,3-biphenyl-4,5-dihydro-1H-pyrazole

Crystal data

C27H21FN2O	F(000) = 428
Mr = 408.46	Dx = 1.281 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 625 reflections
a = 5.9774 (14) Å	θ = 1.4–26.4°
b = 10.484 (3) Å	µ = 0.08 mm^−1
c = 16.896 (4) Å	T = 290 K
β = 90.762 (4)°	Needle, colourless
V = 1058.7 (5) Å^3	0.34 × 0.23 × 0.09 mm
Z = 2

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2272 independent reflections
Radiation source: fine-focus sealed tube	1984 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ϕ and ω scans	θmax = 26.4°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.941, Tmax = 0.992	k = −12→13
8402 measured reflections	l = −20→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	All H-atom parameters refined
S = 1.26	w = 1/[σ^2(Fo^2) + (0.0468P)^2 + 0.0049P] where P = (Fo^2 + 2Fc^2)/3
2272 reflections	(Δ/σ)max < 0.001
364 parameters	Δρmax = 0.12 e Å^−3
1 restraint	Δρmin = −0.12 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
F1	0.3696 (3)	0.49694 (16)	0.86252 (7)	0.0938 (5)
O1	0.1136 (2)	0.29288 (16)	0.82474 (8)	0.0716 (4)
N1	0.5919 (3)	0.03263 (15)	0.63601 (9)	0.0584 (4)
N2	0.4082 (3)	0.00675 (17)	0.58801 (9)	0.0589 (4)
C1	0.3883 (3)	0.09556 (19)	0.53612 (10)	0.0524 (5)
C2	0.5663 (4)	0.1959 (2)	0.54431 (12)	0.0569 (5)
C3	0.6664 (4)	0.16526 (19)	0.62545 (11)	0.0534 (5)
C4	0.5846 (3)	0.25293 (18)	0.69013 (10)	0.0461 (4)
C5	0.7061 (4)	0.3613 (2)	0.70950 (11)	0.0539 (5)
C6	0.6334 (4)	0.4441 (2)	0.76682 (12)	0.0630 (6)
C7	0.4407 (4)	0.4180 (2)	0.80499 (10)	0.0597 (5)
C8	0.3147 (3)	0.3118 (2)	0.78722 (11)	0.0527 (5)
C9	0.3861 (3)	0.2305 (2)	0.72911 (11)	0.0526 (5)
C10	0.1108 (3)	0.21570 (19)	0.89140 (10)	0.0516 (4)
C11	−0.0833 (4)	0.2215 (2)	0.93383 (13)	0.0640 (6)
C12	−0.1063 (5)	0.1468 (3)	1.00022 (14)	0.0768 (7)
C13	0.0624 (5)	0.0666 (3)	1.02321 (14)	0.0791 (7)
C14	0.2548 (4)	0.0613 (3)	0.97995 (14)	0.0743 (7)
C15	0.2810 (4)	0.1363 (2)	0.91360 (12)	0.0622 (6)
C16	0.6137 (3)	−0.03519 (18)	0.70726 (12)	0.0564 (5)
C17	0.7959 (4)	−0.0128 (2)	0.75727 (15)	0.0712 (6)
C18	0.8204 (5)	−0.0802 (3)	0.82630 (15)	0.0836 (8)
C19	0.6672 (6)	−0.1699 (3)	0.84788 (16)	0.0889 (8)
C20	0.4860 (5)	−0.1925 (3)	0.79898 (15)	0.0840 (7)
C21	0.4585 (4)	−0.1255 (2)	0.72916 (14)	0.0686 (6)
C22	0.2111 (3)	0.0925 (2)	0.47531 (10)	0.0549 (5)
C23	0.0446 (4)	0.0010 (2)	0.47625 (13)	0.0613 (5)
C24	−0.1211 (4)	0.0010 (3)	0.41856 (14)	0.0706 (6)
C25	−0.1211 (4)	0.0903 (3)	0.35895 (13)	0.0738 (7)
C26	0.0432 (5)	0.1799 (3)	0.35723 (14)	0.0744 (7)
C27	0.2087 (4)	0.1819 (2)	0.41487 (12)	0.0663 (6)
H2A	0.506 (3)	0.279 (2)	0.5408 (10)	0.056 (5)*
H2B	0.683 (4)	0.185 (2)	0.5028 (12)	0.065 (6)*
H3	0.831 (3)	0.1692 (17)	0.6273 (9)	0.043 (5)*
H5	0.851 (4)	0.371 (2)	0.6832 (11)	0.061 (6)*
H6	0.712 (4)	0.516 (3)	0.7803 (13)	0.079 (7)*
H9	0.298 (4)	0.157 (2)	0.7168 (11)	0.066 (6)*
H11	−0.203 (4)	0.276 (3)	0.9139 (13)	0.085 (8)*
H12	−0.247 (5)	0.157 (3)	1.0292 (16)	0.106 (9)*
H13	0.044 (4)	0.017 (3)	1.0669 (16)	0.094 (8)*
H14	0.372 (4)	0.009 (3)	0.9943 (13)	0.079 (7)*
H15	0.407 (4)	0.132 (2)	0.8850 (12)	0.063 (6)*
H17	0.897 (4)	0.053 (3)	0.7421 (14)	0.082 (7)*
H18	0.943 (4)	−0.067 (2)	0.8614 (14)	0.084 (7)*
H19	0.685 (4)	−0.217 (3)	0.8980 (15)	0.096 (8)*
H20	0.368 (5)	−0.261 (3)	0.8097 (15)	0.097 (8)*
H21	0.337 (4)	−0.138 (2)	0.6944 (13)	0.075 (7)*
H23	0.039 (4)	−0.058 (2)	0.5180 (13)	0.065 (6)*
H24	−0.233 (4)	−0.059 (3)	0.4195 (13)	0.077 (7)*
H25	−0.236 (4)	0.087 (2)	0.3177 (14)	0.082 (7)*
H26	0.054 (4)	0.239 (3)	0.3143 (15)	0.094 (8)*
H27	0.326 (4)	0.241 (3)	0.4139 (13)	0.079 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1201 (12)	0.0920 (11)	0.0700 (8)	0.0086 (9)	0.0256 (8)	−0.0247 (8)
O1	0.0538 (8)	0.0888 (11)	0.0727 (9)	0.0183 (8)	0.0202 (6)	0.0298 (8)
N1	0.0667 (11)	0.0445 (9)	0.0639 (10)	−0.0023 (8)	−0.0079 (8)	−0.0020 (8)
N2	0.0697 (11)	0.0489 (9)	0.0579 (9)	−0.0015 (8)	−0.0064 (8)	−0.0023 (8)
C22	0.0643 (12)	0.0525 (11)	0.0481 (10)	0.0084 (10)	0.0062 (8)	−0.0050 (9)
C1	0.0628 (12)	0.0455 (10)	0.0492 (10)	0.0027 (9)	0.0077 (8)	−0.0045 (9)
C2	0.0681 (13)	0.0504 (13)	0.0526 (10)	0.0017 (11)	0.0178 (9)	−0.0031 (9)
C3	0.0480 (11)	0.0508 (12)	0.0614 (11)	−0.0028 (9)	0.0074 (8)	−0.0039 (9)
C4	0.0467 (10)	0.0441 (10)	0.0474 (9)	−0.0024 (8)	0.0024 (7)	0.0028 (8)
C5	0.0565 (12)	0.0554 (12)	0.0499 (10)	−0.0103 (10)	0.0083 (9)	0.0014 (9)
C7	0.0775 (14)	0.0586 (13)	0.0433 (10)	0.0079 (12)	0.0085 (10)	−0.0012 (9)
C6	0.0780 (15)	0.0553 (13)	0.0559 (12)	−0.0133 (12)	0.0041 (10)	−0.0079 (10)
C8	0.0507 (10)	0.0573 (12)	0.0501 (10)	0.0083 (9)	0.0076 (8)	0.0146 (9)
C9	0.0475 (10)	0.0474 (12)	0.0628 (11)	−0.0030 (9)	0.0040 (8)	0.0043 (9)
C10	0.0533 (11)	0.0513 (11)	0.0504 (9)	−0.0034 (9)	0.0051 (8)	0.0015 (9)
C11	0.0586 (13)	0.0626 (14)	0.0713 (13)	−0.0025 (11)	0.0188 (10)	0.0033 (11)
C12	0.0781 (16)	0.0791 (17)	0.0737 (14)	−0.0120 (14)	0.0250 (13)	0.0047 (13)
C13	0.0920 (19)	0.0856 (19)	0.0600 (13)	−0.0188 (15)	0.0092 (12)	0.0157 (13)
C14	0.0740 (16)	0.0769 (17)	0.0717 (14)	−0.0025 (13)	−0.0088 (12)	0.0190 (12)
C15	0.0537 (12)	0.0746 (15)	0.0585 (11)	0.0007 (11)	0.0057 (10)	0.0083 (11)
C16	0.0650 (12)	0.0408 (10)	0.0630 (11)	0.0055 (9)	−0.0061 (9)	−0.0069 (9)
C17	0.0768 (15)	0.0552 (14)	0.0812 (14)	−0.0020 (12)	−0.0165 (12)	−0.0023 (12)
C18	0.1001 (19)	0.0690 (16)	0.0808 (16)	0.0085 (15)	−0.0339 (15)	−0.0041 (13)
C19	0.125 (2)	0.0653 (16)	0.0752 (15)	0.0119 (16)	−0.0228 (15)	0.0106 (13)
C20	0.105 (2)	0.0618 (15)	0.0850 (17)	−0.0058 (15)	−0.0098 (15)	0.0170 (13)
C21	0.0775 (15)	0.0548 (13)	0.0731 (14)	−0.0025 (12)	−0.0141 (12)	0.0022 (11)
C23	0.0691 (14)	0.0589 (13)	0.0562 (12)	0.0031 (12)	0.0070 (10)	−0.0040 (11)
C24	0.0612 (14)	0.0738 (16)	0.0768 (14)	0.0002 (13)	0.0050 (11)	−0.0188 (13)
C25	0.0767 (16)	0.0834 (17)	0.0611 (13)	0.0240 (14)	−0.0096 (11)	−0.0132 (13)
C26	0.0900 (18)	0.0719 (16)	0.0613 (13)	0.0134 (14)	−0.0030 (12)	0.0037 (12)
C27	0.0742 (15)	0.0647 (15)	0.0599 (12)	0.0031 (12)	0.0026 (11)	0.0018 (11)

Geometric parameters (Å, º)

F1—C7	1.350 (2)	C6—H6	0.91 (3)
O1—C8	1.381 (2)	C8—C7	1.374 (3)
O1—C10	1.387 (2)	C5—H5	0.98 (2)
N1—N2	1.383 (2)	C15—C14	1.380 (3)
N1—C16	1.403 (2)	C15—H15	0.90 (2)
N1—C3	1.472 (3)	C2—H2A	0.94 (2)
N2—C1	1.284 (2)	C2—H2B	1.00 (2)
C10—C15	1.363 (3)	C24—C25	1.375 (4)
C10—C11	1.374 (3)	C24—H24	0.92 (2)
C22—C23	1.383 (3)	C21—C20	1.381 (3)
C22—C27	1.386 (3)	C21—H21	0.94 (2)
C22—C1	1.466 (3)	C27—C26	1.379 (3)
C1—C2	1.501 (3)	C27—H27	0.94 (3)
C16—C21	1.379 (3)	C17—C18	1.370 (4)
C16—C17	1.389 (3)	C17—H17	0.95 (3)
C3—C4	1.514 (3)	C25—C26	1.359 (4)
C3—C2	1.523 (3)	C25—H25	0.97 (2)
C3—H3	0.981 (18)	C13—C12	1.365 (4)
C9—C8	1.373 (3)	C13—C14	1.371 (4)
C9—C4	1.385 (3)	C13—H13	0.91 (3)
C9—H9	0.95 (2)	C12—H12	0.99 (3)
C4—C5	1.385 (3)	C26—H26	0.96 (3)
C23—C24	1.380 (3)	C14—H14	0.92 (2)
C23—H23	0.94 (2)	C20—C19	1.374 (4)
C11—C12	1.376 (3)	C20—H20	1.03 (3)
C11—H11	0.97 (2)	C18—C19	1.365 (4)
C6—C7	1.355 (3)	C18—H18	0.95 (2)
C6—C5	1.376 (3)	C19—H19	0.98 (3)
C8—O1—C10	118.46 (13)	C6—C7—C8	121.77 (18)
N2—N1—C16	117.91 (16)	C10—C15—C14	118.6 (2)
N2—N1—C3	110.68 (15)	C10—C15—H15	120.8 (14)
C16—N1—C3	123.93 (15)	C14—C15—H15	120.5 (14)
C1—N2—N1	108.89 (16)	C1—C2—C3	101.83 (16)
C15—C10—C11	121.05 (19)	C1—C2—H2A	111.9 (12)
C15—C10—O1	124.25 (16)	C3—C2—H2A	113.4 (11)
C11—C10—O1	114.67 (17)	C1—C2—H2B	111.1 (12)
C23—C22—C27	118.50 (19)	C3—C2—H2B	109.9 (11)
C23—C22—C1	121.37 (18)	H2A—C2—H2B	108.6 (18)
C27—C22—C1	120.1 (2)	C25—C24—C23	120.7 (2)
N2—C1—C22	121.49 (18)	C25—C24—H24	119.1 (14)
N2—C1—C2	112.71 (16)	C23—C24—H24	120.2 (14)
C22—C1—C2	125.78 (18)	C16—C21—C20	120.4 (2)
C21—C16—C17	118.5 (2)	C16—C21—H21	116.6 (14)
C21—C16—N1	121.51 (18)	C20—C21—H21	123.1 (14)
C17—C16—N1	120.0 (2)	C26—C27—C22	120.7 (2)
N1—C3—C4	112.65 (15)	C26—C27—H27	121.9 (14)
N1—C3—C2	101.09 (16)	C22—C27—H27	117.4 (14)
C4—C3—C2	113.30 (17)	C18—C17—C16	120.3 (3)
N1—C3—H3	109.8 (10)	C18—C17—H17	122.7 (15)
C4—C3—H3	106.5 (10)	C16—C17—H17	117.0 (14)
C2—C3—H3	113.6 (10)	C26—C25—C24	119.5 (2)
C8—C9—C4	120.73 (19)	C26—C25—H25	121.0 (15)
C8—C9—H9	118.7 (12)	C24—C25—H25	119.4 (15)
C4—C9—H9	120.6 (12)	C12—C13—C14	119.7 (2)
C9—C4—C5	118.47 (17)	C12—C13—H13	119.0 (17)
C9—C4—C3	121.79 (17)	C14—C13—H13	121.4 (17)
C5—C4—C3	119.70 (16)	C13—C12—C11	120.1 (2)
C24—C23—C22	120.1 (2)	C13—C12—H12	124.1 (16)
C24—C23—H23	119.8 (13)	C11—C12—H12	115.8 (16)
C22—C23—H23	120.0 (13)	C25—C26—C27	120.5 (2)
C10—C11—C12	119.6 (2)	C25—C26—H26	121.2 (15)
C10—C11—H11	118.1 (14)	C27—C26—H26	118.2 (15)
C12—C11—H11	122.3 (14)	C13—C14—C15	120.9 (2)
C7—C6—C5	119.1 (2)	C13—C14—H14	121.6 (14)
C7—C6—H6	119.1 (15)	C15—C14—H14	117.4 (14)
C5—C6—H6	121.8 (15)	C19—C20—C21	120.7 (3)
C9—C8—C7	118.97 (17)	C19—C20—H20	123.5 (14)
C9—C8—O1	121.33 (19)	C21—C20—H20	115.8 (14)
C7—C8—O1	119.60 (18)	C19—C18—C17	121.2 (3)
C6—C5—C4	120.96 (19)	C19—C18—H18	116.8 (15)
C6—C5—H5	122.7 (12)	C17—C18—H18	122.0 (15)
C4—C5—H5	116.1 (12)	C18—C19—C20	119.0 (3)
F1—C7—C6	119.7 (2)	C18—C19—H19	120.6 (15)
F1—C7—C8	118.50 (19)	C20—C19—H19	120.4 (15)
C16—N1—N2—C1	165.44 (16)	C9—C4—C5—C6	0.8 (3)
C3—N1—N2—C1	14.4 (2)	C3—C4—C5—C6	178.56 (18)
C8—O1—C10—C15	−14.0 (3)	C5—C6—C7—F1	178.60 (19)
C8—O1—C10—C11	167.89 (18)	C5—C6—C7—C8	−0.9 (3)
N1—N2—C1—C22	178.38 (16)	C9—C8—C7—F1	−179.64 (16)
N1—N2—C1—C2	0.0 (2)	O1—C8—C7—F1	4.0 (3)
C23—C22—C1—N2	6.7 (3)	C9—C8—C7—C6	−0.1 (3)
C27—C22—C1—N2	−172.81 (19)	O1—C8—C7—C6	−176.52 (18)
C23—C22—C1—C2	−175.13 (19)	C11—C10—C15—C14	0.0 (3)
C27—C22—C1—C2	5.3 (3)	O1—C10—C15—C14	−178.0 (2)
N2—N1—C16—C21	0.3 (3)	N2—C1—C2—C3	−13.3 (2)
C3—N1—C16—C21	147.2 (2)	C22—C1—C2—C3	168.44 (17)
N2—N1—C16—C17	179.76 (18)	N1—C3—C2—C1	19.52 (19)
C3—N1—C16—C17	−33.3 (3)	C4—C3—C2—C1	−101.27 (18)
N2—N1—C3—C4	99.68 (18)	C22—C23—C24—C25	1.0 (3)
C16—N1—C3—C4	−49.3 (2)	C17—C16—C21—C20	−0.6 (3)
N2—N1—C3—C2	−21.56 (19)	N1—C16—C21—C20	178.9 (2)
C16—N1—C3—C2	−170.54 (18)	C23—C22—C27—C26	0.3 (3)
C8—C9—C4—C5	−1.8 (2)	C1—C22—C27—C26	179.9 (2)
C8—C9—C4—C3	−179.57 (17)	C21—C16—C17—C18	0.6 (3)
N1—C3—C4—C9	−29.4 (2)	N1—C16—C17—C18	−178.9 (2)
C2—C3—C4—C9	84.6 (2)	C23—C24—C25—C26	−0.4 (3)
N1—C3—C4—C5	152.93 (16)	C14—C13—C12—C11	0.2 (4)
C2—C3—C4—C5	−93.1 (2)	C10—C11—C12—C13	−0.6 (3)
C27—C22—C23—C24	−0.9 (3)	C24—C25—C26—C27	−0.2 (3)
C1—C22—C23—C24	179.52 (18)	C22—C27—C26—C25	0.2 (3)
C15—C10—C11—C12	0.5 (3)	C12—C13—C14—C15	0.3 (4)
O1—C10—C11—C12	178.6 (2)	C10—C15—C14—C13	−0.4 (4)
C4—C9—C8—C7	1.5 (3)	C16—C21—C20—C19	0.4 (4)
C4—C9—C8—O1	177.84 (16)	C16—C17—C18—C19	−0.4 (4)
C10—O1—C8—C9	88.3 (2)	C17—C18—C19—C20	0.2 (4)
C10—O1—C8—C7	−95.4 (2)	C21—C20—C19—C18	−0.2 (4)
C7—C6—C5—C4	0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg3^i	0.95 (3)	2.84 (2)	3.566 (3)	134 (2)
C26—H26···Cg4^ii	0.96 (3)	2.93 (3)	3.755 (3)	145 (2)
C2—H2B···Cg5^i	1.00 (2)	2.80 (2)	3.764 (3)	162 (2)

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

(II) (5S)-3-(4-chlorophenyl)-5-(3-fluoro-4-phenoxyphenyl)-1-phenyl- 4,5-dihydro-1H-pyrazole

Crystal data

C27H20ClFN2O	F(000) = 920
Mr = 442.90	Dx = 1.344 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 725 reflections
a = 17.728 (3) Å	θ = 1.6–26.4°
b = 11.0132 (17) Å	µ = 0.21 mm^−1
c = 11.2709 (17) Å	T = 290 K
β = 95.729 (3)°	Needle, pale yellow
V = 2189.6 (6) Å^3	0.29 × 0.17 × 0.07 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4469 independent reflections
Radiation source: fine-focus sealed tube	2393 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
ϕ and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.937, Tmax = 0.986	k = −13→13
17206 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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0477P)^2 + 0.0424P] where P = (Fo^2 + 2Fc^2)/3
4469 reflections	(Δ/σ)max < 0.001
369 parameters	Δρmax = 0.23 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
Cl1	−0.14938 (5)	0.07794 (9)	0.93387 (8)	0.0825 (3)
F1	0.36663 (10)	0.52203 (15)	0.48064 (17)	0.0752 (6)
O1	0.36171 (13)	0.35176 (19)	0.64496 (19)	0.0722 (7)
N1	0.16461 (13)	0.0477 (2)	0.4709 (2)	0.0506 (6)
N2	0.12363 (13)	0.0251 (2)	0.5646 (2)	0.0487 (6)
C1	0.07004 (16)	0.1043 (3)	0.5655 (3)	0.0467 (7)
C2	0.06958 (19)	0.1933 (3)	0.4649 (3)	0.0552 (9)
C3	0.14286 (16)	0.1617 (3)	0.4093 (3)	0.0486 (8)
C4	0.20398 (15)	0.2574 (2)	0.4272 (2)	0.0408 (7)
C5	0.20967 (18)	0.3478 (3)	0.3430 (3)	0.0520 (8)
C6	0.26321 (19)	0.4372 (3)	0.3607 (3)	0.0565 (9)
C7	0.31297 (17)	0.4349 (3)	0.4613 (3)	0.0504 (8)
C8	0.30998 (17)	0.3452 (3)	0.5456 (3)	0.0476 (7)
C9	0.25438 (17)	0.2584 (3)	0.5288 (3)	0.0484 (8)
C10	0.39964 (16)	0.2493 (3)	0.6902 (3)	0.0535 (8)
C11	0.43454 (19)	0.2617 (4)	0.8037 (3)	0.0626 (9)
C12	0.4766 (2)	0.1661 (5)	0.8544 (4)	0.0805 (12)
C13	0.4831 (2)	0.0600 (5)	0.7938 (4)	0.0842 (12)
C14	0.4478 (2)	0.0488 (4)	0.6812 (4)	0.0814 (12)
C15	0.40646 (19)	0.1434 (4)	0.6279 (3)	0.0654 (10)
C16	0.22564 (16)	−0.0264 (3)	0.4501 (3)	0.0498 (8)
C17	0.26613 (19)	−0.0053 (3)	0.3537 (3)	0.0578 (9)
C18	0.3252 (2)	−0.0813 (3)	0.3313 (4)	0.0728 (11)
C19	0.3447 (3)	−0.1772 (4)	0.4047 (4)	0.0927 (14)
C20	0.3051 (2)	−0.1972 (4)	0.5013 (4)	0.0897 (13)
C21	0.2461 (2)	−0.1232 (3)	0.5242 (3)	0.0670 (10)
C22	0.01699 (16)	0.1006 (3)	0.6562 (3)	0.0458 (7)
C23	0.02627 (19)	0.0184 (3)	0.7499 (3)	0.0542 (8)
C24	−0.02392 (19)	0.0119 (3)	0.8335 (3)	0.0581 (9)
C25	−0.08522 (17)	0.0885 (3)	0.8269 (3)	0.0542 (8)
C26	−0.09649 (18)	0.1718 (3)	0.7360 (3)	0.0584 (9)
C27	−0.04526 (17)	0.1775 (3)	0.6517 (3)	0.0530 (8)
H2A	0.0242 (17)	0.184 (3)	0.409 (3)	0.070 (10)*
H2B	0.0711 (16)	0.276 (3)	0.489 (3)	0.071 (10)*
H3	0.1331 (14)	0.146 (2)	0.325 (2)	0.053 (8)*
H5	0.1738 (16)	0.347 (3)	0.273 (2)	0.067 (10)*
H6	0.2688 (14)	0.502 (2)	0.307 (2)	0.050 (8)*
H9	0.2522 (13)	0.199 (2)	0.583 (2)	0.040 (8)*
H11	0.4279 (15)	0.337 (3)	0.845 (2)	0.056 (9)*
H12	0.4976 (19)	0.181 (3)	0.929 (3)	0.079 (12)*
H13	0.511 (2)	−0.008 (3)	0.834 (3)	0.104 (13)*
H14	0.4506 (18)	−0.027 (3)	0.638 (3)	0.092 (13)*
H15	0.3822 (16)	0.135 (3)	0.552 (3)	0.067 (10)*
H17	0.2523 (16)	0.060 (3)	0.305 (3)	0.064 (10)*
H18	0.3501 (15)	−0.063 (2)	0.263 (3)	0.064 (9)*
H19	0.386 (2)	−0.224 (3)	0.388 (3)	0.096 (12)*
H20	0.318 (2)	−0.263 (3)	0.553 (3)	0.104 (14)*
H21	0.2214 (14)	−0.139 (2)	0.589 (2)	0.058 (8)*
H23	0.0671 (14)	−0.035 (2)	0.756 (2)	0.047 (8)*
H24	−0.0187 (15)	−0.043 (2)	0.891 (2)	0.049 (9)*
H26	−0.1396 (14)	0.224 (2)	0.729 (2)	0.052 (7)*
H27	−0.0558 (14)	0.229 (2)	0.588 (2)	0.050 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0743 (6)	0.0961 (7)	0.0812 (6)	−0.0117 (5)	0.0275 (5)	−0.0099 (5)
F1	0.0707 (12)	0.0494 (11)	0.1054 (15)	−0.0104 (10)	0.0084 (11)	−0.0012 (10)
O1	0.0851 (17)	0.0513 (14)	0.0727 (15)	−0.0006 (13)	−0.0296 (13)	−0.0075 (12)
N1	0.0555 (16)	0.0412 (16)	0.0565 (16)	0.0025 (13)	0.0116 (13)	0.0015 (13)
N2	0.0478 (15)	0.0441 (15)	0.0534 (16)	−0.0036 (13)	0.0013 (12)	−0.0033 (12)
C1	0.0409 (17)	0.0460 (19)	0.0516 (19)	−0.0058 (15)	−0.0032 (15)	−0.0071 (15)
C2	0.049 (2)	0.056 (2)	0.060 (2)	0.0012 (17)	−0.0005 (17)	0.0045 (19)
C3	0.0524 (19)	0.047 (2)	0.0449 (19)	0.0024 (15)	−0.0027 (15)	0.0008 (16)
C4	0.0421 (17)	0.0396 (17)	0.0402 (17)	0.0038 (14)	0.0025 (14)	0.0001 (14)
C5	0.050 (2)	0.057 (2)	0.048 (2)	0.0061 (18)	0.0002 (16)	0.0059 (18)
C6	0.059 (2)	0.048 (2)	0.062 (2)	0.0055 (18)	0.0080 (19)	0.0142 (19)
C7	0.0450 (18)	0.0346 (18)	0.072 (2)	−0.0010 (15)	0.0089 (17)	−0.0045 (17)
C8	0.0535 (19)	0.0388 (18)	0.0487 (19)	0.0048 (16)	−0.0047 (15)	−0.0037 (16)
C9	0.061 (2)	0.0385 (19)	0.0451 (19)	0.0014 (16)	−0.0002 (16)	0.0074 (16)
C10	0.0455 (19)	0.057 (2)	0.056 (2)	−0.0027 (16)	−0.0061 (16)	0.0032 (18)
C11	0.057 (2)	0.070 (3)	0.059 (2)	−0.010 (2)	−0.0050 (18)	−0.001 (2)
C12	0.064 (3)	0.105 (4)	0.068 (3)	−0.003 (3)	−0.014 (2)	0.015 (3)
C13	0.063 (3)	0.092 (4)	0.094 (3)	0.020 (2)	−0.008 (2)	0.020 (3)
C14	0.067 (3)	0.084 (3)	0.091 (3)	0.026 (2)	−0.002 (2)	−0.003 (3)
C15	0.058 (2)	0.074 (3)	0.061 (2)	0.014 (2)	−0.0071 (19)	−0.004 (2)
C16	0.0538 (19)	0.0353 (18)	0.060 (2)	−0.0042 (16)	0.0048 (16)	−0.0057 (16)
C17	0.061 (2)	0.046 (2)	0.067 (2)	−0.0018 (18)	0.0084 (19)	−0.0018 (19)
C18	0.075 (3)	0.061 (2)	0.087 (3)	0.006 (2)	0.032 (2)	0.000 (2)
C19	0.092 (3)	0.063 (3)	0.130 (4)	0.025 (2)	0.044 (3)	0.008 (3)
C20	0.099 (3)	0.065 (3)	0.109 (3)	0.031 (2)	0.032 (3)	0.023 (3)
C21	0.074 (3)	0.052 (2)	0.078 (3)	0.0084 (19)	0.025 (2)	0.007 (2)
C22	0.0456 (18)	0.0397 (18)	0.0503 (18)	−0.0082 (15)	−0.0047 (15)	−0.0060 (15)
C23	0.053 (2)	0.048 (2)	0.061 (2)	0.0024 (18)	0.0033 (18)	−0.0002 (17)
C24	0.067 (2)	0.050 (2)	0.056 (2)	−0.0057 (19)	0.0039 (19)	0.0055 (19)
C25	0.054 (2)	0.051 (2)	0.058 (2)	−0.0135 (17)	0.0043 (16)	−0.0121 (18)
C26	0.0407 (19)	0.053 (2)	0.080 (3)	0.0021 (17)	0.0031 (18)	−0.0076 (19)
C27	0.047 (2)	0.049 (2)	0.061 (2)	−0.0023 (17)	−0.0034 (17)	0.0025 (18)

Geometric parameters (Å, º)

Cl1—C25	1.742 (3)	C26—H26	0.95 (2)
F1—C7	1.354 (3)	C2—H2A	0.98 (3)
O1—C8	1.377 (3)	C2—H2B	0.95 (3)
O1—C10	1.384 (4)	C6—C5	1.369 (4)
N1—N2	1.363 (3)	C6—H6	0.94 (3)
N1—C16	1.394 (3)	C23—C24	1.360 (4)
N1—C3	1.467 (3)	C23—H23	0.93 (2)
N2—C1	1.291 (3)	C5—H5	0.96 (3)
C16—C21	1.380 (4)	C17—C18	1.384 (4)
C16—C17	1.381 (4)	C17—H17	0.92 (3)
C4—C9	1.380 (4)	C24—H24	0.89 (3)
C4—C5	1.386 (4)	C27—H27	0.92 (3)
C4—C3	1.511 (4)	C15—C14	1.377 (5)
C3—C2	1.537 (4)	C15—H15	0.92 (3)
C3—H3	0.97 (3)	C21—C20	1.370 (5)
C22—C23	1.388 (4)	C21—H21	0.90 (2)
C22—C27	1.388 (4)	C18—C19	1.364 (5)
C22—C1	1.457 (4)	C18—H18	0.95 (3)
C9—C8	1.373 (4)	C11—C12	1.381 (5)
C9—H9	0.90 (2)	C11—H11	0.96 (3)
C1—C2	1.498 (4)	C12—C13	1.364 (6)
C10—C11	1.372 (4)	C12—H12	0.90 (3)
C10—C15	1.372 (4)	C14—C13	1.363 (5)
C7—C6	1.365 (4)	C14—H14	0.97 (3)
C7—C8	1.375 (4)	C13—H13	0.98 (4)
C25—C24	1.372 (4)	C19—C20	1.370 (5)
C25—C26	1.375 (4)	C19—H19	0.93 (3)
C26—C27	1.380 (4)	C20—H20	0.95 (4)
Cl1···Cg2^i	3.560 (2)
C8—O1—C10	121.1 (2)	C5—C6—H6	124.3 (16)
N2—N1—C16	120.4 (2)	C24—C23—C22	121.6 (3)
N2—N1—C3	112.8 (2)	C24—C23—H23	118.4 (16)
C16—N1—C3	126.4 (2)	C22—C23—H23	120.0 (16)
C1—N2—N1	109.4 (2)	C9—C8—C7	118.8 (3)
C21—C16—C17	118.7 (3)	C9—C8—O1	124.0 (3)
C21—C16—N1	120.8 (3)	C7—C8—O1	117.2 (3)
C17—C16—N1	120.5 (3)	C6—C5—C4	120.9 (3)
C9—C4—C5	118.5 (3)	C6—C5—H5	121.3 (17)
C9—C4—C3	120.8 (3)	C4—C5—H5	117.7 (17)
C5—C4—C3	120.7 (3)	C16—C17—C18	120.3 (4)
N1—C3—C4	112.5 (2)	C16—C17—H17	118.2 (18)
N1—C3—C2	101.2 (2)	C18—C17—H17	121.6 (18)
C4—C3—C2	114.3 (3)	C23—C24—C25	120.0 (3)
N1—C3—H3	108.8 (16)	C23—C24—H24	121.1 (17)
C4—C3—H3	108.4 (15)	C25—C24—H24	118.9 (17)
C2—C3—H3	111.5 (15)	C26—C27—C22	121.5 (3)
C23—C22—C27	117.3 (3)	C26—C27—H27	118.0 (16)
C23—C22—C1	121.1 (3)	C22—C27—H27	120.3 (16)
C27—C22—C1	121.6 (3)	C10—C15—C14	119.3 (4)
C8—C9—C4	121.1 (3)	C10—C15—H15	120.0 (19)
C8—C9—H9	119.6 (16)	C14—C15—H15	121 (2)
C4—C9—H9	119.2 (16)	C20—C21—C16	120.4 (4)
N2—C1—C22	120.9 (3)	C20—C21—H21	118.5 (17)
N2—C1—C2	112.6 (3)	C16—C21—H21	121.1 (17)
C22—C1—C2	126.5 (3)	C19—C18—C17	120.5 (4)
C11—C10—C15	120.5 (3)	C19—C18—H18	123.1 (17)
C11—C10—O1	114.8 (3)	C17—C18—H18	116.3 (17)
C15—C10—O1	124.7 (3)	C10—C11—C12	119.0 (4)
F1—C7—C6	120.4 (3)	C10—C11—H11	118.2 (17)
F1—C7—C8	118.2 (3)	C12—C11—H11	122.8 (17)
C6—C7—C8	121.4 (3)	C13—C12—C11	121.0 (4)
C24—C25—C26	120.4 (3)	C13—C12—H12	125 (2)
C24—C25—Cl1	119.4 (3)	C11—C12—H12	113 (2)
C26—C25—Cl1	120.3 (3)	C13—C14—C15	120.8 (5)
C25—C26—C27	119.1 (3)	C13—C14—H14	120 (2)
C25—C26—H26	121.1 (14)	C15—C14—H14	119 (2)
C27—C26—H26	119.7 (15)	C14—C13—C12	119.3 (4)
C1—C2—C3	102.7 (3)	C14—C13—H13	121 (2)
C1—C2—H2A	111.5 (17)	C12—C13—H13	119 (2)
C3—C2—H2A	112.7 (16)	C18—C19—C20	119.2 (4)
C1—C2—H2B	114.6 (18)	C18—C19—H19	118 (2)
C3—C2—H2B	109.3 (17)	C20—C19—H19	123 (2)
H2A—C2—H2B	106 (2)	C21—C20—C19	121.0 (4)
C7—C6—C5	119.3 (3)	C21—C20—H20	119 (2)
C7—C6—H6	116.4 (16)	C19—C20—H20	120 (2)
C16—N1—N2—C1	−179.5 (2)	C4—C9—C8—C7	2.6 (4)
C3—N1—N2—C1	7.4 (3)	C4—C9—C8—O1	179.7 (3)
N2—N1—C16—C21	−0.5 (4)	F1—C7—C8—C9	178.0 (2)
C3—N1—C16—C21	171.6 (3)	C6—C7—C8—C9	−1.6 (4)
N2—N1—C16—C17	178.5 (3)	F1—C7—C8—O1	0.7 (4)
C3—N1—C16—C17	−9.4 (4)	C6—C7—C8—O1	−178.9 (3)
N2—N1—C3—C4	111.1 (3)	C10—O1—C8—C9	46.3 (4)
C16—N1—C3—C4	−61.5 (4)	C10—O1—C8—C7	−136.5 (3)
N2—N1—C3—C2	−11.3 (3)	C7—C6—C5—C4	1.9 (4)
C16—N1—C3—C2	176.1 (3)	C9—C4—C5—C6	−1.0 (4)
C9—C4—C3—N1	−28.2 (4)	C3—C4—C5—C6	177.6 (3)
C5—C4—C3—N1	153.2 (3)	C21—C16—C17—C18	1.0 (5)
C9—C4—C3—C2	86.5 (3)	N1—C16—C17—C18	−178.1 (3)
C5—C4—C3—C2	−92.1 (3)	C22—C23—C24—C25	−0.5 (5)
C5—C4—C9—C8	−1.3 (4)	C26—C25—C24—C23	0.2 (5)
C3—C4—C9—C8	−179.9 (3)	Cl1—C25—C24—C23	179.4 (2)
N1—N2—C1—C22	179.5 (2)	C25—C26—C27—C22	0.5 (4)
N1—N2—C1—C2	0.5 (3)	C23—C22—C27—C26	−0.8 (4)
C23—C22—C1—N2	5.4 (4)	C1—C22—C27—C26	178.3 (3)
C27—C22—C1—N2	−173.6 (3)	C11—C10—C15—C14	0.9 (5)
C23—C22—C1—C2	−175.7 (3)	O1—C10—C15—C14	177.8 (3)
C27—C22—C1—C2	5.2 (4)	C17—C16—C21—C20	−0.6 (5)
C8—O1—C10—C11	−164.6 (3)	N1—C16—C21—C20	178.5 (3)
C8—O1—C10—C15	18.4 (4)	C16—C17—C18—C19	−0.6 (5)
C24—C25—C26—C27	−0.2 (5)	C15—C10—C11—C12	0.1 (5)
Cl1—C25—C26—C27	−179.4 (2)	O1—C10—C11—C12	−177.1 (3)
N2—C1—C2—C3	−7.4 (4)	C10—C11—C12—C13	−0.8 (6)
C22—C1—C2—C3	173.7 (3)	C10—C15—C14—C13	−1.2 (6)
N1—C3—C2—C1	10.4 (3)	C15—C14—C13—C12	0.5 (6)
C4—C3—C2—C1	−110.8 (3)	C11—C12—C13—C14	0.6 (6)
F1—C7—C6—C5	179.7 (3)	C17—C18—C19—C20	−0.3 (6)
C8—C7—C6—C5	−0.6 (4)	C16—C21—C20—C19	−0.3 (6)
C27—C22—C23—C24	0.8 (4)	C18—C19—C20—C21	0.7 (7)
C1—C22—C23—C24	−178.3 (3)

Symmetry code: (i) −x, y−1/2, −z+3/2.

(III) (5R)-5-(3-fluoro-4-phenoxyphenyl)-3-(4-methylphenyl)-1-phenyl- 4,5-dihydro-1H-pyrazole

Crystal data

C28H23FN2O	F(000) = 888
Mr = 422.48	Dx = 1.279 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 650 reflections
a = 17.742 (6) Å	θ = 1.7–25.4°
b = 11.099 (4) Å	µ = 0.08 mm^−1
c = 11.187 (4) Å	T = 290 K
β = 95.293 (6)°	Needle, colourless
V = 2193.5 (13) Å^3	0.40 × 0.40 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4427 independent reflections
Radiation source: fine-focus sealed tube	2845 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ϕ and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.921, Tmax = 0.990	k = −12→13
16874 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0465P)^2 + 0.2251P] where P = (Fo^2 + 2Fc^2)/3
4427 reflections	(Δ/σ)max = 0.026
370 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.14 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	0.36457 (6)	0.52122 (10)	0.48041 (11)	0.0789 (4)
N1	0.16717 (8)	0.04657 (13)	0.47688 (13)	0.0561 (4)
N2	0.12514 (8)	0.02362 (13)	0.57057 (13)	0.0522 (4)
O1	0.36300 (8)	0.35104 (12)	0.64487 (12)	0.0743 (4)
C1	0.07122 (9)	0.10149 (15)	0.57005 (15)	0.0485 (4)
C2	0.07102 (11)	0.1889 (2)	0.46820 (19)	0.0595 (5)
C3	0.14470 (10)	0.15831 (16)	0.41309 (17)	0.0532 (5)
C4	0.20465 (9)	0.25532 (15)	0.43068 (14)	0.0465 (4)
C5	0.20859 (11)	0.34545 (18)	0.34638 (17)	0.0559 (5)
C6	0.26171 (11)	0.43565 (19)	0.36304 (19)	0.0612 (5)
C7	0.31209 (10)	0.43342 (16)	0.46265 (18)	0.0548 (5)
C8	0.31083 (10)	0.34383 (16)	0.54660 (15)	0.0521 (4)
C9	0.25569 (10)	0.25630 (17)	0.53151 (16)	0.0504 (4)
C10	0.40066 (10)	0.24909 (18)	0.69112 (17)	0.0562 (5)
C11	0.43529 (11)	0.2623 (2)	0.80495 (18)	0.0655 (5)
C12	0.47669 (12)	0.1678 (3)	0.8572 (2)	0.0800 (7)
C13	0.48311 (13)	0.0620 (3)	0.7966 (3)	0.0845 (7)
C14	0.44831 (13)	0.0499 (2)	0.6836 (3)	0.0828 (7)
C15	0.40713 (11)	0.1437 (2)	0.6287 (2)	0.0682 (6)
C16	0.22829 (10)	−0.02612 (16)	0.45608 (17)	0.0536 (5)
C17	0.26903 (11)	−0.00421 (19)	0.3588 (2)	0.0612 (5)
C18	0.32853 (13)	−0.0784 (2)	0.3367 (2)	0.0768 (6)
C19	0.34846 (16)	−0.1737 (2)	0.4101 (3)	0.0946 (8)
C20	0.30878 (15)	−0.1941 (2)	0.5075 (3)	0.0941 (8)
C21	0.24916 (13)	−0.12180 (18)	0.5313 (2)	0.0703 (6)
C22	0.01698 (9)	0.09830 (15)	0.65971 (15)	0.0495 (4)
C23	0.02339 (11)	0.01524 (19)	0.75263 (18)	0.0598 (5)
C24	−0.02915 (12)	0.0104 (2)	0.83540 (19)	0.0652 (5)
C25	−0.09007 (11)	0.08810 (18)	0.83000 (17)	0.0604 (5)
C26	−0.09657 (11)	0.17169 (19)	0.7384 (2)	0.0658 (6)
C27	−0.04383 (11)	0.17657 (18)	0.6547 (2)	0.0611 (5)
C28	−0.14806 (12)	0.0796 (2)	0.9199 (2)	0.0850 (7)
H2A	0.0283 (11)	0.1762 (16)	0.4122 (17)	0.069 (6)*
H2B	0.0712 (10)	0.2710 (19)	0.4959 (16)	0.071 (6)*
H3	0.1352 (8)	0.1420 (14)	0.3288 (15)	0.050 (5)*
H5	0.1739 (10)	0.3470 (16)	0.2778 (16)	0.063 (5)*
H6	0.2658 (10)	0.4977 (17)	0.3069 (17)	0.070 (6)*
H9	0.2545 (9)	0.1947 (15)	0.5877 (14)	0.049 (5)*
H11	0.4289 (10)	0.3385 (17)	0.8470 (16)	0.070 (6)*
H12	0.4996 (12)	0.1772 (19)	0.936 (2)	0.094 (7)*
H13	0.5117 (15)	0.000 (2)	0.834 (2)	0.112 (9)*
H14	0.4518 (12)	−0.023 (2)	0.639 (2)	0.097 (8)*
H15	0.3844 (10)	0.1351 (17)	0.5476 (17)	0.072 (6)*
H17	0.2576 (10)	0.0616 (16)	0.3080 (16)	0.061 (6)*
H18	0.3528 (11)	−0.0596 (17)	0.2694 (18)	0.075 (6)*
H19	0.3918 (14)	−0.221 (2)	0.394 (2)	0.108 (8)*
H20	0.3226 (13)	−0.256 (2)	0.562 (2)	0.101 (8)*
H21	0.2236 (10)	−0.1371 (17)	0.6002 (17)	0.074 (6)*
H23	0.0642 (10)	−0.0404 (17)	0.7614 (16)	0.067 (6)*
H24	−0.0234 (12)	−0.0509 (19)	0.903 (2)	0.096 (7)*
H26	−0.1418 (10)	0.2305 (17)	0.7325 (15)	0.067 (5)*
H27	−0.0503 (9)	0.2336 (16)	0.5906 (15)	0.056 (5)*
H28A	−0.1979	0.0795	0.8785	0.127*
H28B	−0.1428	0.1475	0.9733	0.127*
H28C	−0.1404	0.0066	0.9653	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0740 (8)	0.0545 (7)	0.1088 (10)	−0.0111 (6)	0.0116 (7)	−0.0003 (6)
N1	0.0577 (9)	0.0494 (9)	0.0627 (10)	0.0037 (7)	0.0131 (8)	0.0014 (7)
N2	0.0530 (9)	0.0479 (9)	0.0556 (9)	−0.0041 (7)	0.0045 (7)	−0.0052 (7)
O1	0.0839 (9)	0.0552 (8)	0.0774 (9)	0.0001 (8)	−0.0269 (8)	−0.0069 (7)
C1	0.0439 (10)	0.0478 (11)	0.0520 (10)	−0.0033 (9)	−0.0041 (8)	−0.0071 (8)
C2	0.0496 (12)	0.0611 (14)	0.0668 (13)	0.0014 (10)	−0.0011 (10)	0.0021 (11)
C3	0.0536 (11)	0.0565 (12)	0.0487 (11)	0.0038 (9)	0.0003 (9)	−0.0003 (9)
C4	0.0463 (10)	0.0486 (10)	0.0445 (9)	0.0068 (8)	0.0039 (8)	−0.0001 (8)
C5	0.0546 (11)	0.0634 (13)	0.0490 (11)	0.0095 (10)	0.0008 (9)	0.0072 (10)
C6	0.0632 (13)	0.0562 (13)	0.0654 (13)	0.0092 (11)	0.0134 (11)	0.0178 (11)
C7	0.0496 (10)	0.0428 (11)	0.0730 (13)	0.0008 (9)	0.0116 (10)	−0.0021 (10)
C8	0.0542 (10)	0.0469 (11)	0.0539 (11)	0.0063 (9)	−0.0022 (9)	−0.0036 (9)
C9	0.0607 (11)	0.0446 (11)	0.0456 (10)	0.0040 (9)	0.0031 (9)	0.0055 (9)
C10	0.0479 (10)	0.0597 (13)	0.0597 (11)	−0.0044 (9)	−0.0024 (9)	0.0035 (10)
C11	0.0589 (12)	0.0750 (15)	0.0605 (12)	−0.0118 (11)	−0.0052 (10)	−0.0002 (12)
C12	0.0618 (14)	0.110 (2)	0.0653 (15)	−0.0062 (14)	−0.0107 (11)	0.0145 (15)
C13	0.0600 (14)	0.097 (2)	0.0943 (19)	0.0162 (14)	−0.0049 (13)	0.0194 (17)
C14	0.0665 (14)	0.0834 (18)	0.0969 (19)	0.0238 (13)	−0.0004 (13)	−0.0037 (15)
C15	0.0605 (13)	0.0784 (16)	0.0636 (13)	0.0131 (11)	−0.0055 (10)	−0.0058 (12)
C16	0.0521 (11)	0.0427 (10)	0.0662 (12)	−0.0027 (9)	0.0063 (9)	−0.0098 (9)
C17	0.0621 (13)	0.0527 (13)	0.0697 (13)	0.0007 (10)	0.0114 (10)	−0.0039 (10)
C18	0.0756 (15)	0.0670 (15)	0.0920 (17)	0.0028 (12)	0.0299 (13)	−0.0039 (13)
C19	0.0862 (17)	0.0717 (17)	0.132 (2)	0.0227 (14)	0.0410 (17)	0.0062 (16)
C20	0.0980 (19)	0.0669 (16)	0.122 (2)	0.0277 (14)	0.0325 (17)	0.0224 (16)
C21	0.0750 (14)	0.0524 (13)	0.0861 (16)	0.0076 (11)	0.0213 (12)	0.0074 (11)
C22	0.0443 (10)	0.0482 (11)	0.0547 (11)	−0.0051 (8)	−0.0015 (8)	−0.0073 (9)
C23	0.0566 (12)	0.0575 (13)	0.0650 (13)	0.0038 (10)	0.0032 (10)	−0.0010 (10)
C24	0.0674 (13)	0.0626 (13)	0.0664 (13)	−0.0044 (11)	0.0101 (11)	−0.0016 (11)
C25	0.0560 (11)	0.0575 (12)	0.0687 (13)	−0.0120 (10)	0.0108 (10)	−0.0106 (10)
C26	0.0488 (11)	0.0604 (14)	0.0892 (15)	0.0008 (10)	0.0112 (11)	−0.0061 (12)
C27	0.0515 (11)	0.0581 (13)	0.0732 (14)	−0.0016 (10)	0.0038 (10)	0.0033 (11)
C28	0.0739 (14)	0.0914 (17)	0.0929 (16)	−0.0115 (13)	0.0258 (12)	−0.0105 (13)

Geometric parameters (Å, º)

F1—C7	1.350 (2)	C25—C26	1.380 (3)
N2—C1	1.289 (2)	C25—C28	1.507 (3)
N2—N1	1.365 (2)	C10—C11	1.370 (3)
C16—C17	1.383 (3)	C10—C15	1.372 (3)
C16—C21	1.384 (3)	C17—C18	1.379 (3)
C16—N1	1.388 (2)	C17—H17	0.937 (17)
N1—C3	1.468 (2)	C24—H24	1.01 (2)
C1—C22	1.453 (2)	C2—H2A	0.948 (19)
C1—C2	1.496 (3)	C2—H2B	0.96 (2)
C8—C7	1.369 (2)	C21—C20	1.373 (3)
C8—O1	1.373 (2)	C21—H21	0.946 (19)
C8—C9	1.378 (2)	C15—C14	1.383 (3)
C22—C27	1.382 (2)	C15—H15	0.963 (18)
C22—C23	1.386 (3)	C11—C12	1.379 (3)
C7—C6	1.363 (3)	C11—H11	0.979 (19)
C27—C26	1.384 (3)	C26—H26	1.032 (18)
C27—H27	0.956 (17)	C28—H28A	0.9600
C9—C4	1.380 (2)	C28—H28B	0.9600
C9—H9	0.930 (16)	C28—H28C	0.9600
C5—C6	1.376 (3)	C14—C13	1.361 (3)
C5—C4	1.381 (2)	C14—H14	0.96 (2)
C5—H5	0.938 (18)	C13—C12	1.366 (4)
C4—C3	1.514 (2)	C13—H13	0.93 (3)
O1—C10	1.389 (2)	C18—C19	1.366 (3)
C3—C2	1.534 (3)	C18—H18	0.92 (2)
C3—H3	0.960 (16)	C12—H12	0.95 (2)
C23—C24	1.374 (3)	C20—C19	1.369 (3)
C23—H23	0.950 (18)	C20—H20	0.94 (2)
C6—H6	0.940 (19)	C19—H19	0.96 (2)
C25—C24	1.379 (3)
C1—N2—N1	109.22 (14)	C15—C10—O1	124.37 (17)
C17—C16—C21	118.94 (19)	C18—C17—C16	120.0 (2)
C17—C16—N1	120.19 (18)	C18—C17—H17	119.0 (11)
C21—C16—N1	120.87 (17)	C16—C17—H17	121.0 (11)
N2—N1—C16	120.71 (15)	C23—C24—C25	121.6 (2)
N2—N1—C3	112.82 (14)	C23—C24—H24	120.0 (13)
C16—N1—C3	126.22 (15)	C25—C24—H24	118.4 (13)
N2—C1—C22	121.27 (16)	C1—C2—C3	102.72 (15)
N2—C1—C2	112.83 (16)	C1—C2—H2A	110.6 (11)
C22—C1—C2	125.89 (16)	C3—C2—H2A	111.1 (11)
C7—C8—O1	117.04 (17)	C1—C2—H2B	111.7 (11)
C7—C8—C9	118.96 (17)	C3—C2—H2B	111.2 (11)
O1—C8—C9	123.90 (16)	H2A—C2—H2B	109.4 (16)
C27—C22—C23	117.27 (18)	C20—C21—C16	119.9 (2)
C27—C22—C1	121.38 (17)	C20—C21—H21	119.3 (12)
C23—C22—C1	121.34 (16)	C16—C21—H21	120.8 (12)
F1—C7—C6	119.92 (17)	C10—C15—C14	118.8 (2)
F1—C7—C8	118.55 (17)	C10—C15—H15	121.1 (12)
C6—C7—C8	121.53 (18)	C14—C15—H15	120.1 (12)
C22—C27—C26	121.4 (2)	C10—C11—C12	119.2 (2)
C22—C27—H27	119.1 (10)	C10—C11—H11	118.5 (11)
C26—C27—H27	119.4 (10)	C12—C11—H11	122.2 (11)
C8—C9—C4	120.71 (17)	C25—C26—C27	120.9 (2)
C8—C9—H9	119.7 (10)	C25—C26—H26	119.0 (10)
C4—C9—H9	119.5 (10)	C27—C26—H26	120.1 (10)
C6—C5—C4	120.78 (19)	C25—C28—H28A	109.5
C6—C5—H5	119.1 (11)	C25—C28—H28B	109.5
C4—C5—H5	120.1 (11)	H28A—C28—H28B	109.5
C9—C4—C5	118.80 (17)	C25—C28—H28C	109.5
C9—C4—C3	120.81 (16)	H28A—C28—H28C	109.5
C5—C4—C3	120.38 (16)	H28B—C28—H28C	109.5
C8—O1—C10	121.09 (14)	C13—C14—C15	120.9 (3)
N1—C3—C4	112.45 (14)	C13—C14—H14	121.6 (14)
N1—C3—C2	101.25 (15)	C15—C14—H14	117.4 (14)
C4—C3—C2	113.88 (16)	C14—C13—C12	119.6 (3)
N1—C3—H3	109.5 (10)	C14—C13—H13	121.5 (16)
C4—C3—H3	108.7 (9)	C12—C13—H13	118.9 (16)
C2—C3—H3	110.9 (9)	C19—C18—C17	121.0 (2)
C24—C23—C22	121.2 (2)	C19—C18—H18	123.3 (12)
C24—C23—H23	117.6 (11)	C17—C18—H18	115.7 (13)
C22—C23—H23	121.2 (11)	C13—C12—C11	120.6 (2)
C7—C6—C5	119.14 (19)	C13—C12—H12	120.7 (13)
C7—C6—H6	118.3 (12)	C11—C12—H12	118.7 (14)
C5—C6—H6	122.6 (12)	C19—C20—C21	121.3 (3)
C24—C25—C26	117.67 (19)	C19—C20—H20	121.1 (14)
C24—C25—C28	120.82 (19)	C21—C20—H20	117.5 (14)
C26—C25—C28	121.50 (19)	C18—C19—C20	118.9 (2)
C11—C10—C15	120.8 (2)	C18—C19—H19	118.7 (14)
C11—C10—O1	114.72 (18)	C20—C19—H19	122.3 (14)
C1—N2—N1—C16	−178.90 (15)	C27—C22—C23—C24	0.7 (3)
C1—N2—N1—C3	6.47 (19)	C1—C22—C23—C24	−178.25 (17)
C17—C16—N1—N2	178.02 (16)	F1—C7—C6—C5	−179.99 (16)
C21—C16—N1—N2	−1.5 (3)	C8—C7—C6—C5	−0.3 (3)
C17—C16—N1—C3	−8.1 (3)	C4—C5—C6—C7	1.8 (3)
C21—C16—N1—C3	172.35 (18)	C8—O1—C10—C11	−163.65 (17)
N1—N2—C1—C22	179.59 (14)	C8—O1—C10—C15	19.4 (3)
N1—N2—C1—C2	0.9 (2)	C21—C16—C17—C18	1.1 (3)
N2—C1—C22—C27	−175.60 (16)	N1—C16—C17—C18	−178.40 (18)
C2—C1—C22—C27	2.9 (3)	C22—C23—C24—C25	−0.3 (3)
N2—C1—C22—C23	3.3 (2)	C26—C25—C24—C23	−0.2 (3)
C2—C1—C22—C23	−178.28 (18)	C28—C25—C24—C23	178.63 (19)
O1—C8—C7—F1	1.0 (2)	N2—C1—C2—C3	−7.3 (2)
C9—C8—C7—F1	177.61 (15)	C22—C1—C2—C3	174.14 (16)
O1—C8—C7—C6	−178.74 (16)	N1—C3—C2—C1	9.83 (19)
C9—C8—C7—C6	−2.1 (3)	C4—C3—C2—C1	−111.09 (18)
C23—C22—C27—C26	−0.5 (3)	C17—C16—C21—C20	−1.0 (3)
C1—C22—C27—C26	178.41 (17)	N1—C16—C21—C20	178.5 (2)
C7—C8—C9—C4	3.1 (3)	C11—C10—C15—C14	1.1 (3)
O1—C8—C9—C4	179.42 (16)	O1—C10—C15—C14	177.88 (18)
C8—C9—C4—C5	−1.6 (3)	C15—C10—C11—C12	−0.4 (3)
C8—C9—C4—C3	179.17 (16)	O1—C10—C11—C12	−177.49 (17)
C6—C5—C4—C9	−0.9 (3)	C24—C25—C26—C27	0.3 (3)
C6—C5—C4—C3	178.40 (16)	C28—C25—C26—C27	−178.46 (18)
C7—C8—O1—C10	−138.84 (17)	C22—C27—C26—C25	0.0 (3)
C9—C8—O1—C10	44.7 (2)	C10—C15—C14—C13	−1.2 (3)
N2—N1—C3—C4	111.48 (16)	C15—C14—C13—C12	0.7 (4)
C16—N1—C3—C4	−62.8 (2)	C16—C17—C18—C19	−0.3 (3)
N2—N1—C3—C2	−10.44 (19)	C14—C13—C12—C11	0.0 (4)
C16—N1—C3—C2	175.28 (17)	C10—C11—C12—C13	−0.2 (3)
C9—C4—C3—N1	−25.8 (2)	C16—C21—C20—C19	0.0 (4)
C5—C4—C3—N1	154.98 (16)	C17—C18—C19—C20	−0.7 (4)
C9—C4—C3—C2	88.7 (2)	C21—C20—C19—C18	0.8 (4)
C5—C4—C3—C2	−90.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28C···Cg2^i	0.96	3.00	3.663 (3)	128

Symmetry code: (i) −x, y−1/2, −z+3/2.

(IV) (5S)-5-(3-fluoro-4-phenoxyphenyl)-3-(4-methoxyphenyl)-1-phenyl- 4,5-dihydro-1H-pyrazole

Crystal data

C28H23FN2O2	F(000) = 920
Mr = 438.48	Dx = 1.312 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 560 reflections
a = 20.274 (4) Å	θ = 1.6–25.4°
b = 5.7588 (12) Å	µ = 0.09 mm^−1
c = 21.241 (4) Å	T = 290 K
β = 116.438 (4)°	Needle, colourless
V = 2220.6 (8) Å^3	0.40 × 0.35 × 0.09 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4445 independent reflections
Radiation source: fine-focus sealed tube	2297 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
ϕ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→24
Tmin = 0.943, Tmax = 0.992	k = −7→7
16344 measured reflections	l = −26→26

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0344P)^2] where P = (Fo^2 + 2Fc^2)/3
4445 reflections	(Δ/σ)max < 0.001
379 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.14 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	0.44345 (11)	0.4707 (4)	0.15403 (11)	0.0920 (8)
O1	0.49444 (13)	0.0567 (4)	0.12657 (13)	0.0800 (8)
O2	1.00036 (13)	0.0144 (4)	0.08204 (12)	0.0692 (7)
N1	0.77153 (14)	0.0767 (4)	0.28946 (14)	0.0506 (7)
N2	0.82019 (14)	0.0002 (5)	0.26409 (14)	0.0515 (7)
C1	0.82552 (17)	0.1524 (6)	0.22232 (18)	0.0491 (9)
C2	0.7789 (2)	0.3617 (7)	0.2148 (3)	0.0631 (11)
C3	0.74785 (19)	0.3177 (6)	0.2673 (2)	0.0527 (10)
C4	0.66598 (17)	0.3562 (5)	0.23776 (16)	0.0464 (9)
C5	0.6389 (2)	0.5567 (6)	0.25252 (19)	0.0574 (10)
C6	0.5639 (2)	0.5979 (8)	0.2232 (2)	0.0653 (11)
C7	0.5169 (2)	0.4351 (7)	0.1806 (2)	0.0603 (10)
C8	0.5418 (2)	0.2327 (6)	0.16490 (17)	0.0547 (10)
C9	0.6165 (2)	0.1948 (6)	0.19355 (17)	0.0510 (9)
C10	0.44082 (19)	0.1015 (6)	0.0590 (2)	0.0608 (10)
C11	0.4453 (3)	0.2707 (9)	0.0169 (3)	0.0990 (18)
C12	0.3896 (3)	0.2967 (10)	−0.0498 (3)	0.1010 (17)
C13	0.3310 (3)	0.1541 (9)	−0.0743 (2)	0.0799 (13)
C14	0.3276 (3)	−0.0146 (9)	−0.0322 (3)	0.0909 (16)
C15	0.3828 (2)	−0.0449 (7)	0.0346 (2)	0.0780 (13)
C16	0.78237 (18)	−0.0112 (5)	0.35506 (18)	0.0467 (9)
C17	0.7372 (2)	0.0600 (7)	0.3844 (2)	0.0675 (11)
C18	0.7443 (2)	−0.0366 (8)	0.4468 (2)	0.0787 (13)
C19	0.7970 (2)	−0.1995 (8)	0.4807 (2)	0.0716 (12)
C20	0.8420 (2)	−0.2680 (7)	0.4522 (2)	0.0678 (12)
C21	0.8352 (2)	−0.1758 (6)	0.3903 (2)	0.0562 (10)
C22	0.87143 (17)	0.1128 (6)	0.18632 (17)	0.0485 (9)
C23	0.9171 (2)	−0.0806 (6)	0.20101 (19)	0.0579 (10)
C24	0.9607 (2)	−0.1188 (7)	0.16775 (19)	0.0574 (10)
C25	0.95985 (18)	0.0375 (6)	0.11848 (18)	0.0531 (9)
C26	0.9152 (2)	0.2306 (7)	0.1032 (2)	0.0613 (11)
C27	0.8720 (2)	0.2672 (7)	0.1370 (2)	0.0589 (10)
C28	1.03949 (19)	−0.1965 (7)	0.0894 (2)	0.0834 (13)
H2A	0.8059 (16)	0.504 (5)	0.2237 (16)	0.065 (11)*
H2B	0.7425 (18)	0.372 (5)	0.1680 (18)	0.075 (13)*
H3	0.7718 (13)	0.411 (4)	0.3086 (13)	0.044 (8)*
H5	0.6718 (17)	0.671 (6)	0.2822 (17)	0.080 (12)*
H6	0.5448 (16)	0.737 (5)	0.2322 (15)	0.063 (11)*
H9	0.6338 (14)	0.053 (5)	0.1869 (13)	0.044 (9)*
H11	0.480 (2)	0.371 (7)	0.033 (2)	0.100 (16)*
H12	0.391 (2)	0.419 (8)	−0.078 (2)	0.132 (19)*
H13	0.2925 (19)	0.176 (6)	−0.1223 (19)	0.094 (13)*
H14	0.291 (2)	−0.108 (7)	−0.045 (2)	0.097 (16)*
H15	0.3828 (18)	−0.162 (6)	0.0672 (19)	0.095 (14)*
H17	0.6991 (18)	0.181 (6)	0.3599 (17)	0.092 (13)*
H18	0.7098 (19)	0.021 (6)	0.4633 (18)	0.088 (13)*
H19	0.8003 (15)	−0.271 (5)	0.5224 (16)	0.063 (11)*
H20	0.8761 (18)	−0.385 (6)	0.4743 (17)	0.082 (13)*
H21	0.8677 (15)	−0.212 (5)	0.3718 (14)	0.048 (10)*
H23	0.9164 (14)	−0.189 (5)	0.2350 (14)	0.049 (9)*
H24	0.9922 (16)	−0.263 (6)	0.1797 (16)	0.073 (11)*
H26	0.9140 (16)	0.334 (6)	0.0679 (16)	0.074 (12)*
H27	0.8416 (14)	0.400 (5)	0.1249 (13)	0.052 (8)*
H28A	1.0770	−0.2112	0.1369	0.125*
H28B	1.0619	−0.1958	0.0580	0.125*
H28C	1.0060	−0.3251	0.0783	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0511 (14)	0.1177 (19)	0.1039 (17)	0.0223 (12)	0.0316 (13)	0.0378 (14)
O1	0.0571 (16)	0.0650 (17)	0.0776 (19)	−0.0179 (14)	−0.0064 (15)	0.0244 (14)
O2	0.0629 (17)	0.0748 (18)	0.0728 (18)	0.0035 (14)	0.0330 (15)	0.0106 (14)
N1	0.0470 (18)	0.0454 (17)	0.0516 (19)	0.0095 (14)	0.0149 (15)	0.0049 (14)
N2	0.0495 (18)	0.0498 (18)	0.0465 (18)	0.0045 (14)	0.0135 (15)	−0.0006 (15)
C1	0.044 (2)	0.045 (2)	0.046 (2)	−0.0033 (17)	0.0082 (18)	0.0033 (18)
C2	0.058 (3)	0.052 (3)	0.074 (3)	−0.002 (2)	0.025 (3)	0.009 (2)
C4	0.045 (2)	0.043 (2)	0.044 (2)	0.0025 (17)	0.0130 (17)	0.0052 (17)
C3	0.047 (2)	0.045 (2)	0.052 (3)	0.0002 (18)	0.0088 (19)	−0.0062 (19)
C16	0.040 (2)	0.045 (2)	0.042 (2)	−0.0008 (17)	0.0059 (17)	−0.0020 (18)
C5	0.059 (3)	0.046 (2)	0.059 (3)	0.005 (2)	0.019 (2)	−0.003 (2)
C6	0.066 (3)	0.062 (3)	0.068 (3)	0.023 (3)	0.030 (2)	0.011 (2)
C7	0.039 (2)	0.078 (3)	0.062 (3)	0.012 (2)	0.021 (2)	0.026 (2)
C8	0.045 (2)	0.052 (2)	0.052 (2)	−0.002 (2)	0.0083 (19)	0.0172 (19)
C9	0.051 (3)	0.038 (2)	0.055 (2)	0.003 (2)	0.0152 (19)	0.0032 (18)
C10	0.041 (2)	0.062 (2)	0.062 (3)	−0.003 (2)	0.007 (2)	0.010 (2)
C11	0.073 (3)	0.120 (4)	0.074 (4)	−0.044 (3)	0.006 (3)	0.030 (3)
C12	0.091 (4)	0.119 (4)	0.062 (3)	−0.028 (3)	0.007 (3)	0.025 (3)
C13	0.079 (4)	0.083 (3)	0.049 (3)	−0.002 (3)	0.004 (3)	−0.006 (3)
C14	0.065 (3)	0.085 (4)	0.086 (4)	−0.017 (3)	0.001 (3)	−0.004 (3)
C15	0.063 (3)	0.072 (3)	0.073 (3)	−0.016 (2)	0.006 (3)	0.013 (3)
C17	0.060 (3)	0.082 (3)	0.053 (3)	0.026 (2)	0.019 (2)	0.006 (2)
C18	0.069 (3)	0.104 (4)	0.066 (3)	0.022 (3)	0.033 (3)	0.001 (3)
C19	0.074 (3)	0.084 (3)	0.055 (3)	0.009 (3)	0.026 (3)	0.009 (3)
C20	0.065 (3)	0.074 (3)	0.054 (3)	0.017 (2)	0.017 (2)	0.008 (2)
C21	0.047 (2)	0.064 (3)	0.053 (3)	0.010 (2)	0.017 (2)	0.003 (2)
C22	0.042 (2)	0.045 (2)	0.045 (2)	−0.0070 (18)	0.0070 (18)	−0.0004 (18)
C23	0.062 (3)	0.055 (3)	0.047 (2)	0.004 (2)	0.016 (2)	0.014 (2)
C24	0.054 (3)	0.060 (3)	0.057 (3)	0.008 (2)	0.024 (2)	0.006 (2)
C25	0.043 (2)	0.060 (3)	0.049 (2)	−0.009 (2)	0.0152 (19)	0.001 (2)
C26	0.061 (3)	0.056 (3)	0.062 (3)	−0.002 (2)	0.023 (2)	0.012 (2)
C27	0.055 (3)	0.046 (2)	0.067 (3)	0.005 (2)	0.020 (2)	0.005 (2)
C28	0.068 (3)	0.102 (3)	0.092 (3)	0.023 (3)	0.045 (2)	0.020 (3)

Geometric parameters (Å, º)

F1—C7	1.352 (3)	C9—H9	0.92 (3)
O1—C8	1.384 (4)	C10—C15	1.349 (5)
O1—C10	1.386 (4)	C10—C11	1.352 (5)
O2—C25	1.363 (4)	C20—C19	1.360 (5)
O2—C28	1.421 (4)	C20—H20	0.93 (3)
N1—N2	1.390 (3)	C25—C24	1.375 (5)
N1—C16	1.405 (4)	C25—C26	1.378 (5)
N1—C3	1.476 (4)	C23—C24	1.373 (5)
N2—C1	1.286 (4)	C23—H23	0.96 (3)
C22—C27	1.378 (4)	C2—H2A	0.96 (3)
C22—C23	1.392 (4)	C2—H2B	0.94 (3)
C22—C1	1.462 (4)	C24—H24	1.01 (3)
C1—C2	1.496 (5)	C26—H26	0.95 (3)
C16—C21	1.376 (4)	C13—C14	1.343 (6)
C16—C17	1.380 (5)	C13—C12	1.344 (6)
C4—C5	1.374 (4)	C13—H13	0.98 (3)
C4—C9	1.384 (4)	C17—C18	1.385 (5)
C4—C3	1.507 (4)	C17—H17	1.00 (3)
C8—C7	1.370 (5)	C19—C18	1.362 (5)
C8—C9	1.374 (4)	C19—H19	0.95 (3)
C3—C2	1.526 (5)	C12—C11	1.372 (5)
C3—H3	0.96 (2)	C12—H12	0.94 (4)
C21—C20	1.367 (5)	C28—H28A	0.9600
C21—H21	0.93 (3)	C28—H28B	0.9600
C27—C26	1.373 (5)	C28—H28C	0.9600
C27—H27	0.94 (2)	C18—H18	0.97 (3)
C6—C7	1.356 (5)	C14—C15	1.372 (5)
C6—C5	1.382 (5)	C14—H14	0.86 (4)
C6—H6	0.94 (3)	C15—H15	0.97 (3)
C5—H5	0.95 (3)	C11—H11	0.85 (4)
C8—O1—C10	119.5 (3)	C6—C7—C8	121.6 (4)
C25—O2—C28	118.0 (3)	O2—C25—C24	124.2 (4)
N2—N1—C16	116.5 (3)	O2—C25—C26	116.4 (4)
N2—N1—C3	111.1 (3)	C24—C25—C26	119.5 (4)
C16—N1—C3	122.7 (3)	C24—C23—C22	122.0 (4)
C1—N2—N1	110.1 (3)	C24—C23—H23	120.9 (16)
C27—C22—C23	117.1 (4)	C22—C23—H23	117.2 (16)
C27—C22—C1	121.4 (3)	C1—C2—C3	103.6 (3)
C23—C22—C1	121.5 (3)	C1—C2—H2A	113.0 (18)
N2—C1—C22	121.6 (3)	C3—C2—H2A	112.6 (19)
N2—C1—C2	112.3 (3)	C1—C2—H2B	109 (2)
C22—C1—C2	126.1 (3)	C3—C2—H2B	114 (2)
C21—C16—C17	118.2 (4)	H2A—C2—H2B	105 (3)
C21—C16—N1	121.8 (3)	C23—C24—C25	119.6 (4)
C17—C16—N1	119.9 (3)	C23—C24—H24	119.0 (18)
C5—C4—C9	118.4 (3)	C25—C24—H24	121.4 (18)
C5—C4—C3	120.5 (3)	C27—C26—C25	120.4 (4)
C9—C4—C3	121.0 (3)	C27—C26—H26	121.2 (19)
C7—C8—C9	118.8 (3)	C25—C26—H26	118.4 (19)
C7—C8—O1	122.1 (3)	C14—C13—C12	118.8 (5)
C9—C8—O1	118.9 (3)	C14—C13—H13	122 (2)
N1—C3—C4	114.4 (3)	C12—C13—H13	119 (2)
N1—C3—C2	102.0 (3)	C16—C17—C18	120.4 (4)
C4—C3—C2	114.1 (3)	C16—C17—H17	119 (2)
N1—C3—H3	106.1 (15)	C18—C17—H17	120 (2)
C4—C3—H3	108.3 (15)	C20—C19—C18	119.3 (5)
C2—C3—H3	111.7 (15)	C20—C19—H19	120.3 (18)
C20—C21—C16	120.7 (4)	C18—C19—H19	120.3 (18)
C20—C21—H21	122.1 (18)	C13—C12—C11	120.9 (5)
C16—C21—H21	117.0 (18)	C13—C12—H12	119 (3)
C26—C27—C22	121.5 (4)	C11—C12—H12	120 (3)
C26—C27—H27	118.2 (16)	O2—C28—H28A	109.5
C22—C27—H27	120.3 (16)	O2—C28—H28B	109.5
C7—C6—C5	119.2 (4)	H28A—C28—H28B	109.5
C7—C6—H6	119.3 (18)	O2—C28—H28C	109.5
C5—C6—H6	121.5 (19)	H28A—C28—H28C	109.5
C4—C5—C6	120.9 (4)	H28B—C28—H28C	109.5
C4—C5—H5	120.0 (19)	C19—C18—C17	120.4 (4)
C6—C5—H5	119.1 (19)	C19—C18—H18	125 (2)
C8—C9—C4	121.1 (4)	C17—C18—H18	115 (2)
C8—C9—H9	119.5 (17)	C13—C14—C15	121.4 (5)
C4—C9—H9	119.1 (17)	C13—C14—H14	122 (3)
C15—C10—C11	120.1 (4)	C15—C14—H14	116 (3)
C15—C10—O1	115.4 (4)	C10—C15—C14	119.2 (5)
C11—C10—O1	124.5 (3)	C10—C15—H15	116 (2)
C19—C20—C21	121.0 (4)	C14—C15—H15	125 (2)
C19—C20—H20	119 (2)	C10—C11—C12	119.6 (5)
C21—C20—H20	120 (2)	C10—C11—H11	120 (3)
F1—C7—C6	119.4 (4)	C12—C11—H11	120 (3)
F1—C7—C8	119.0 (4)
C16—N1—N2—C1	−153.6 (3)	C16—C21—C20—C19	−0.1 (6)
C3—N1—N2—C1	−6.4 (3)	C5—C6—C7—F1	177.4 (3)
N1—N2—C1—C22	−178.0 (2)	C5—C6—C7—C8	−1.1 (6)
N1—N2—C1—C2	0.5 (4)	C9—C8—C7—F1	−178.3 (3)
C27—C22—C1—N2	174.3 (3)	O1—C8—C7—F1	−4.4 (5)
C23—C22—C1—N2	−6.6 (5)	C9—C8—C7—C6	0.3 (5)
C27—C22—C1—C2	−4.0 (5)	O1—C8—C7—C6	174.2 (3)
C23—C22—C1—C2	175.1 (4)	C28—O2—C25—C24	7.4 (5)
N2—N1—C16—C21	−4.1 (4)	C28—O2—C25—C26	−171.9 (3)
C3—N1—C16—C21	−147.2 (3)	C27—C22—C23—C24	−0.5 (5)
N2—N1—C16—C17	178.8 (3)	C1—C22—C23—C24	−179.7 (3)
C3—N1—C16—C17	35.7 (4)	N2—C1—C2—C3	5.2 (4)
C10—O1—C8—C7	59.7 (5)	C22—C1—C2—C3	−176.3 (3)
C10—O1—C8—C9	−126.4 (3)	N1—C3—C2—C1	−8.1 (4)
N2—N1—C3—C4	132.8 (3)	C4—C3—C2—C1	−132.0 (3)
C16—N1—C3—C4	−82.4 (4)	C22—C23—C24—C25	0.2 (5)
N2—N1—C3—C2	9.1 (4)	O2—C25—C24—C23	−179.3 (3)
C16—N1—C3—C2	153.9 (3)	C26—C25—C24—C23	0.0 (5)
C5—C4—C3—N1	141.5 (3)	C22—C27—C26—C25	−0.6 (5)
C9—C4—C3—N1	−40.5 (4)	O2—C25—C26—C27	179.5 (3)
C5—C4—C3—C2	−101.5 (4)	C24—C25—C26—C27	0.2 (5)
C9—C4—C3—C2	76.4 (4)	C21—C16—C17—C18	−1.4 (5)
C17—C16—C21—C20	0.8 (5)	N1—C16—C17—C18	175.9 (3)
N1—C16—C21—C20	−176.4 (3)	C21—C20—C19—C18	0.1 (6)
C23—C22—C27—C26	0.7 (5)	C14—C13—C12—C11	0.3 (8)
C1—C22—C27—C26	179.9 (3)	C20—C19—C18—C17	−0.6 (6)
C9—C4—C5—C6	−0.8 (5)	C16—C17—C18—C19	1.3 (6)
C3—C4—C5—C6	177.2 (3)	C12—C13—C14—C15	−0.7 (8)
C7—C6—C5—C4	1.4 (6)	C11—C10—C15—C14	−2.2 (7)
C7—C8—C9—C4	0.3 (5)	O1—C10—C15—C14	−179.2 (4)
O1—C8—C9—C4	−173.8 (3)	C13—C14—C15—C10	1.6 (7)
C5—C4—C9—C8	0.0 (5)	C15—C10—C11—C12	1.9 (7)
C3—C4—C9—C8	−178.0 (3)	O1—C10—C11—C12	178.6 (4)
C8—O1—C10—C15	−158.2 (4)	C13—C12—C11—C10	−1.0 (8)
C8—O1—C10—C11	24.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···Cg1^i	0.96	2.77	3.681 (4)	160

Symmetry code: (i) −x+2, y−1/2, −z+1/2.