4,5-Bis(4-fluoro­phen­yl)-5-hy­droxy-3-(2-methyl­propano­yl)-1-phenyl­pyrrolidin-2-one

Huang, J.-Y.; Zhou, F.

doi:10.1107/S1600536811008786

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o873-o874

doi:10.1107/S1600536811008786

Open

access

4,5-Bis(4-fluorophenyl)-5-hydroxy-3-(2-methylpropanoyl)-1-phenylpyrrolidin-2-one

Jian-Ying Huang ^a ^* and Fengyan Zhou ^b

^aDepartment of Applied Chemistry, Zhejiang Gongshang University, Hangzhou 310035, People's Republic of China, and ^bDepartment of Chemistry, Zaozhuang University, Shandong, People's Republic of China
^*Correspondence e-mail: huangjy@mail.zjgsu.edu.cn

(Received 3 December 2010; accepted 8 March 2011; online 12 March 2011)

The title compound, C₂₆H₂₃F₂NO₃, was synthesized by the reaction of 2-(4-fluorobenzylidene)-4-methyl-3-oxo-N-phenylpentanamide and 4-fluorobenzaldehyde. The dihedral angles between the mean plane through the pyrrolidine ring (nearly planar; maximum deviation of 0.145 Å for the C atom bearing the hydroxy group) with the phenyl and benzene rings are 37.22 (7), 51.88 (7) and 87.64 (9)°, respectively. The pyyolidine ring is near coplaner, with max offset of 0.145 A for C19 atom.\uff09 In the crystal, molecules are linked by pairs of O—H⋯O hydrogen bonds into inversion dimers, which are further assembled into chains parallel to the b axis by weak C—H⋯O hydrogen bonds.

Related literature

The title compound is an impurity in the preparation of an intermediate in the synthesis of atorvastatin {systematic name [R-(R^*,R^*)]-2-(4-fluorophenyl)-ρ,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptenoic acid}, see: Baumann et al. (1992 ); Sagyam et al. (2007 ). For the use of atorvastatin as a hypolipidemic and hypocholesterolemic agent, see: Lea & McTavish, (1997 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₆H₂₃F₂NO₃
M_r = 435.45
Monoclinic, C 2/c
a = 24.506 (4) Å
b = 10.2180 (15) Å
c = 20.554 (3) Å
β = 121.963 (2)°
V = 4366.5 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 153 K
0.15 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.986, T_max = 0.990
10716 measured reflections
4091 independent reflections
2471 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.103
S = 1.02
4091 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1ⁱ	0.95	2.59	3.489 (3)	157
O2—H2⋯O1ⁱⁱ	0.84	1.93	2.7625 (18)	174
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008786/rz2536sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008786/rz2536Isup2.hkl

checkCIF report

Comment top

Atorvastatin, {[R-(R^*,R^*)]-2-(4-fluorophenyl)-ρ,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptenoic acid}, is a selective and competitive inhibitor of the enzyme hydroxyl-methylglutaryl coenzyme-A reductase (HMG-CoA-R), which plays a key role in the biosynthesis of cholesterol. By virtue of that activity atorvastatin is useful as a hypolipidemic and hypocholesterolemic agent (Lea & McTavish, 1997). The synthesis of atorvastatin is carried out via the critical intermediate 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-pentanoic acid phenylamide (Sagyam et al., 20077; Baumann et al., 1992). The process for preparing this intermediate is particularly sensitive and vulnerable to the formation of some impurities which may cause product rejection and decreased yields. We report here the crystal structure of one of these impurities.

In the title compound (Fig. 1) bond lengths and angles are within normal ranges (Allen et al., 1987). The five atoms of the pyrrolidine ring are not coplanar, with deviations from the planarity ranging from -0.124 (2) to 0.163 (2) Å. The dihedral angles between the mean plane through the pyrrolidine ring with the C13–C18 phenyl ring and the C1–C6, C7–C12 benzene rings are 37.22 (7), 51.88 (7)° and 87.64 (9)°, respectively. In the crystal structure, the molecules are linked by intermolecular O—H···O hydrogen bonds into dinuclear units (Table 1). The dinuclear units are further assembled into one–dimensional chains along the [010] direction by C–H···O hydrogen bonds.

Related literature top

The title compound is an impurity in the preparation of 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-pentanoic acid, a critical intermediate in the synthesis of atorvastatin {systematic name [R-(R^*,R^*)]-2-(4-fluorophenyl)-ρ,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1- heptenoic acid}, see: Baumann et al. (1992); Sagyam et al. (2007). For the use of atorvastatin as a hypolipidemic and hypocholesterolemic agent, see: Lea & McTavish, (1997). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 2-(4-fluorobenzylidene)-4-methyl-3-oxo-N-phenylpentanamide (5.10 g, 16.4 mmol), ethyl hydroxyethylmethyl thiazolium bromide (0.60 g, 2.38 mmol), 4-fluorobenzaldehyde (2.16 g, 17.4 mmol) and triethylamine (1.20 g, 11.9 mmol) was heated with stirring to 338 K. The reaction mixture was allowed to stand for 24 h at this temperature. Then 2-propanol (6.0 ml) was added and the mixture was heated to about 373 K. Deionized water (6.0 ml) was dropwise added to the reaction mixture over 30 min while maintaining the temperature at 338 K. After it was gradually cooled to 273 K, a white solid was isolated on a filter and washed with 2-propanol. The solid was recrystallized from ethyl acetate/hexane (1:1 v/v) and dried under vacuum at 323 K to give the title product as a white solid (2.28 g, yield 32%). Colourless crystals were obtained by vapor diffusion of pentane into an acetone solution over a period of 5 d.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP view of the title compound. Dispalcement ellipsoids are drawn at 30% probability level.

4,5-Bis(4-fluorophenyl)-5-hydroxy-3-(2-methylpropanoyl)-1-phenylpyrrolidin-2-one top

Crystal data top

C₂₆H₂₃F₂NO₃	F(000) = 1824
M_r = 435.45	D_x = 1.325 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 10716 reflections
a = 24.506 (4) Å	θ = 2.0–25.6°
b = 10.2180 (15) Å	µ = 0.10 mm⁻¹
c = 20.554 (3) Å	T = 153 K
β = 121.963 (2)°	Prism, colourless
V = 4366.5 (11) Å³	0.15 × 0.15 × 0.10 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	4091 independent reflections
Radiation source: fine-focus sealed tube	2471 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −29→20
T_min = 0.986, T_max = 0.990	k = −12→12
10716 measured reflections	l = −21→25

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0294P)² + 3.1716P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4091 reflections	Δρ_max = 0.15 e Å⁻³
293 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00069 (13)

Crystal data top

C₂₆H₂₃F₂NO₃	V = 4366.5 (11) Å³
M_r = 435.45	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.506 (4) Å	µ = 0.10 mm⁻¹
b = 10.2180 (15) Å	T = 153 K
c = 20.554 (3) Å	0.15 × 0.15 × 0.10 mm
β = 121.963 (2)°

Data collection top

Bruker SMART CCD diffractometer	4091 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2471 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.990	R_int = 0.033
10716 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
4091 reflections	Δρ_min = −0.18 e Å⁻³
293 parameters

Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.29729 (8)	0.50006 (17)	0.53453 (10)	0.0981 (6)
F2	0.42759 (8)	0.66971 (13)	0.21676 (8)	0.0818 (5)
O1	0.48023 (6)	−0.09701 (13)	0.40993 (8)	0.0442 (4)
O2	0.50669 (6)	0.28658 (13)	0.48691 (7)	0.0412 (4)
H2	0.5080	0.2276	0.5162	0.062*
O3	0.32087 (8)	0.03185 (16)	0.26703 (10)	0.0698 (5)
N1	0.49052 (7)	0.12325 (15)	0.39667 (9)	0.0350 (4)
C1	0.37194 (9)	0.2815 (2)	0.43135 (12)	0.0413 (5)
C2	0.35015 (11)	0.4082 (2)	0.40746 (14)	0.0562 (6)
H2A	0.3519	0.4446	0.3661	0.067*
C3	0.36879 (12)	0.2328 (2)	0.49159 (13)	0.0608 (7)
H3	0.3842	0.1469	0.5097	0.073*
C4	0.32592 (12)	0.4824 (2)	0.44287 (16)	0.0670 (7)
H4	0.3120	0.5698	0.4269	0.080*
C5	0.32242 (12)	0.4286 (3)	0.50057 (15)	0.0653 (7)
C6	0.34365 (13)	0.3059 (3)	0.52658 (15)	0.0721 (8)
H6	0.3414	0.2708	0.5679	0.086*
C7	0.46243 (9)	0.35844 (19)	0.35938 (11)	0.0361 (5)
C8	0.43194 (10)	0.3401 (2)	0.28104 (12)	0.0473 (6)
H8	0.4186	0.2547	0.2602	0.057*
C9	0.48343 (10)	0.48238 (19)	0.38900 (12)	0.0443 (5)
H9	0.5059	0.4958	0.4429	0.053*
C10	0.47203 (12)	0.5871 (2)	0.34077 (13)	0.0530 (6)
H10	0.4862	0.6725	0.3610	0.064*
C11	0.42063 (12)	0.4446 (2)	0.23262 (13)	0.0555 (6)
H11	0.3997	0.4323	0.1788	0.067*
C12	0.44041 (12)	0.5657 (2)	0.26446 (13)	0.0530 (6)
C13	0.54700 (9)	0.11424 (19)	0.39270 (11)	0.0377 (5)
C14	0.55081 (11)	0.0173 (2)	0.34826 (12)	0.0503 (6)
H14	0.5164	−0.0429	0.3213	0.060*
C15	0.59694 (10)	0.2022 (2)	0.43122 (13)	0.0512 (6)
H15	0.5948	0.2695	0.4617	0.061*
C16	0.60423 (12)	0.0077 (3)	0.34296 (14)	0.0604 (7)
H16	0.6066	−0.0597	0.3127	0.072*
C17	0.65415 (12)	0.0945 (3)	0.38100 (15)	0.0653 (7)
H17	0.6909	0.0879	0.3770	0.078*
C18	0.65041 (11)	0.1906 (3)	0.42466 (15)	0.0659 (7)
H18	0.6850	0.2507	0.4511	0.079*
C19	0.46645 (9)	0.24691 (18)	0.41043 (11)	0.0357 (5)
C20	0.39741 (9)	0.20473 (18)	0.39012 (11)	0.0370 (5)
H20	0.3676	0.2227	0.3342	0.044*
C21	0.40032 (9)	0.05602 (18)	0.39926 (11)	0.0361 (5)
H21	0.4023	0.0310	0.4475	0.043*
C22	0.46109 (9)	0.01616 (19)	0.40310 (10)	0.0348 (5)
C23	0.34501 (10)	−0.0155 (2)	0.33026 (13)	0.0440 (5)
C24	0.32304 (11)	−0.1444 (2)	0.34376 (15)	0.0612 (7)
H24	0.3593	−0.1843	0.3917	0.073*
C25	0.30332 (16)	−0.2382 (3)	0.27765 (19)	0.1080 (12)
H25A	0.2696	−0.1979	0.2298	0.162*
H25B	0.2870	−0.3193	0.2866	0.162*
H25C	0.3407	−0.2579	0.2738	0.162*
C26	0.26836 (15)	−0.1156 (4)	0.3559 (2)	0.1135 (13)
H26C	0.2831	−0.0539	0.3985	0.170*
H26B	0.2544	−0.1971	0.3680	0.170*
H26A	0.2323	−0.0772	0.3091	0.170*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0963 (12)	0.1070 (13)	0.1038 (12)	0.0287 (10)	0.0616 (11)	−0.0280 (10)
F2	0.1209 (13)	0.0551 (9)	0.0778 (10)	0.0180 (8)	0.0583 (10)	0.0305 (8)
O1	0.0472 (9)	0.0305 (8)	0.0572 (9)	0.0039 (7)	0.0291 (8)	0.0038 (7)
O2	0.0471 (8)	0.0362 (8)	0.0350 (8)	−0.0071 (7)	0.0183 (7)	−0.0017 (6)
O3	0.0736 (12)	0.0648 (11)	0.0495 (10)	−0.0192 (9)	0.0180 (9)	−0.0024 (9)
N1	0.0328 (9)	0.0298 (9)	0.0419 (10)	0.0008 (7)	0.0195 (8)	0.0006 (7)
C1	0.0320 (11)	0.0418 (12)	0.0455 (12)	0.0033 (9)	0.0174 (10)	−0.0048 (10)
C2	0.0540 (15)	0.0462 (14)	0.0736 (16)	0.0108 (11)	0.0374 (14)	0.0034 (12)
C3	0.0721 (17)	0.0615 (16)	0.0571 (15)	0.0233 (13)	0.0398 (14)	0.0070 (12)
C4	0.0627 (17)	0.0484 (15)	0.092 (2)	0.0155 (12)	0.0419 (16)	−0.0056 (14)
C5	0.0519 (16)	0.0776 (19)	0.0657 (17)	0.0131 (14)	0.0307 (14)	−0.0216 (15)
C6	0.0793 (19)	0.086 (2)	0.0597 (16)	0.0261 (16)	0.0425 (15)	0.0023 (15)
C7	0.0393 (11)	0.0329 (11)	0.0389 (11)	0.0028 (9)	0.0226 (10)	0.0010 (9)
C8	0.0578 (14)	0.0382 (12)	0.0428 (13)	−0.0006 (10)	0.0246 (11)	−0.0028 (10)
C9	0.0580 (14)	0.0356 (12)	0.0413 (12)	−0.0037 (10)	0.0277 (11)	−0.0017 (10)
C10	0.0792 (17)	0.0305 (12)	0.0596 (15)	−0.0012 (11)	0.0438 (14)	0.0004 (11)
C11	0.0697 (17)	0.0540 (15)	0.0412 (13)	0.0036 (12)	0.0282 (12)	0.0054 (11)
C12	0.0720 (17)	0.0404 (13)	0.0577 (15)	0.0123 (12)	0.0420 (14)	0.0161 (12)
C13	0.0331 (11)	0.0377 (11)	0.0409 (12)	0.0032 (9)	0.0187 (10)	0.0055 (9)
C14	0.0523 (14)	0.0516 (14)	0.0537 (14)	−0.0020 (11)	0.0327 (12)	−0.0017 (11)
C15	0.0390 (13)	0.0498 (14)	0.0614 (14)	−0.0043 (11)	0.0243 (11)	−0.0029 (11)
C16	0.0642 (17)	0.0649 (16)	0.0687 (16)	0.0097 (14)	0.0465 (14)	0.0043 (13)
C17	0.0474 (16)	0.081 (2)	0.0783 (18)	0.0121 (14)	0.0407 (15)	0.0148 (15)
C18	0.0391 (14)	0.0732 (18)	0.0823 (18)	−0.0084 (12)	0.0300 (14)	0.0022 (15)
C19	0.0372 (11)	0.0321 (11)	0.0353 (11)	0.0002 (9)	0.0176 (9)	−0.0027 (9)
C20	0.0356 (11)	0.0334 (11)	0.0391 (11)	0.0022 (9)	0.0178 (9)	0.0007 (9)
C21	0.0364 (11)	0.0343 (11)	0.0382 (11)	−0.0016 (9)	0.0202 (10)	−0.0005 (9)
C22	0.0351 (11)	0.0316 (11)	0.0344 (11)	−0.0004 (9)	0.0161 (9)	−0.0009 (9)
C23	0.0347 (12)	0.0431 (13)	0.0516 (14)	−0.0005 (10)	0.0210 (11)	−0.0016 (11)
C24	0.0427 (14)	0.0458 (14)	0.0762 (17)	−0.0102 (11)	0.0186 (13)	0.0069 (13)
C25	0.095 (2)	0.0598 (19)	0.122 (3)	−0.0212 (17)	0.025 (2)	−0.0242 (19)
C26	0.081 (2)	0.118 (3)	0.168 (3)	−0.005 (2)	0.083 (3)	0.035 (3)

Geometric parameters (Å, º) top

F1—C5	1.362 (3)	C11—C12	1.363 (3)
F2—C12	1.365 (2)	C11—H11	0.9500
O1—C22	1.228 (2)	C13—C15	1.381 (3)
O2—C19	1.402 (2)	C13—C14	1.384 (3)
O2—H2	0.8400	C14—C16	1.373 (3)
O3—C23	1.208 (2)	C14—H14	0.9500
N1—C22	1.355 (2)	C15—C18	1.392 (3)
N1—C13	1.432 (2)	C15—H15	0.9500
N1—C19	1.484 (2)	C16—C17	1.372 (3)
C1—C3	1.374 (3)	C16—H16	0.9500
C1—C2	1.387 (3)	C17—C18	1.366 (3)
C1—C20	1.511 (3)	C17—H17	0.9500
C2—C4	1.384 (3)	C18—H18	0.9500
C2—H2A	0.9500	C19—C20	1.573 (3)
C3—C6	1.387 (3)	C20—C21	1.528 (3)
C3—H3	0.9500	C20—H20	1.0000
C4—C5	1.351 (3)	C21—C22	1.505 (3)
C4—H4	0.9500	C21—C23	1.532 (3)
C5—C6	1.354 (4)	C21—H21	1.0000
C6—H6	0.9500	C23—C24	1.504 (3)
C7—C9	1.381 (3)	C24—C26	1.516 (4)
C7—C8	1.383 (3)	C24—C25	1.517 (4)
C7—C19	1.517 (3)	C24—H24	1.0000
C8—C11	1.384 (3)	C25—H25A	0.9800
C8—H8	0.9500	C25—H25B	0.9800
C9—C10	1.383 (3)	C25—H25C	0.9800
C9—H9	0.9500	C26—H26C	0.9800
C10—C12	1.350 (3)	C26—H26B	0.9800
C10—H10	0.9500	C26—H26A	0.9800

C19—O2—H2	109.5	C17—C16—H16	119.7
C22—N1—C13	122.29 (16)	C14—C16—H16	119.7
C22—N1—C19	112.54 (15)	C18—C17—C16	119.3 (2)
C13—N1—C19	124.01 (15)	C18—C17—H17	120.3
C3—C1—C2	117.6 (2)	C16—C17—H17	120.3
C3—C1—C20	123.64 (19)	C17—C18—C15	121.3 (2)
C2—C1—C20	118.81 (19)	C17—C18—H18	119.4
C4—C2—C1	121.2 (2)	C15—C18—H18	119.4
C4—C2—H2A	119.4	O2—C19—N1	110.20 (15)
C1—C2—H2A	119.4	O2—C19—C7	107.93 (15)
C1—C3—C6	121.6 (2)	N1—C19—C7	113.26 (15)
C1—C3—H3	119.2	O2—C19—C20	113.32 (15)
C6—C3—H3	119.2	N1—C19—C20	101.33 (14)
C5—C4—C2	118.9 (2)	C7—C19—C20	110.82 (16)
C5—C4—H4	120.6	C1—C20—C21	116.98 (16)
C2—C4—H4	120.6	C1—C20—C19	114.49 (16)
C4—C5—C6	122.3 (2)	C21—C20—C19	105.44 (15)
C4—C5—F1	119.2 (3)	C1—C20—H20	106.4
C6—C5—F1	118.5 (3)	C21—C20—H20	106.4
C5—C6—C3	118.5 (2)	C19—C20—H20	106.4
C5—C6—H6	120.7	C22—C21—C20	104.83 (15)
C3—C6—H6	120.7	C22—C21—C23	106.58 (15)
C9—C7—C8	118.89 (18)	C20—C21—C23	113.56 (16)
C9—C7—C19	120.76 (17)	C22—C21—H21	110.5
C8—C7—C19	120.06 (17)	C20—C21—H21	110.5
C7—C8—C11	120.8 (2)	C23—C21—H21	110.5
C7—C8—H8	119.6	O1—C22—N1	125.51 (18)
C11—C8—H8	119.6	O1—C22—C21	124.65 (17)
C7—C9—C10	120.45 (19)	N1—C22—C21	109.84 (16)
C7—C9—H9	119.8	O3—C23—C24	122.0 (2)
C10—C9—H9	119.8	O3—C23—C21	119.63 (19)
C12—C10—C9	118.8 (2)	C24—C23—C21	118.35 (19)
C12—C10—H10	120.6	C23—C24—C26	107.1 (2)
C9—C10—H10	120.6	C23—C24—C25	111.3 (2)
C12—C11—C8	118.0 (2)	C26—C24—C25	112.3 (2)
C12—C11—H11	121.0	C23—C24—H24	108.7
C8—C11—H11	121.0	C26—C24—H24	108.7
C10—C12—C11	123.0 (2)	C25—C24—H24	108.7
C10—C12—F2	118.7 (2)	C24—C25—H25A	109.5
C11—C12—F2	118.3 (2)	C24—C25—H25B	109.5
C15—C13—C14	119.70 (19)	H25A—C25—H25B	109.5
C15—C13—N1	121.04 (18)	C24—C25—H25C	109.5
C14—C13—N1	119.25 (18)	H25A—C25—H25C	109.5
C16—C14—C13	120.3 (2)	H25B—C25—H25C	109.5
C16—C14—H14	119.9	C24—C26—H26C	109.5
C13—C14—H14	119.9	C24—C26—H26B	109.5
C13—C15—C18	118.9 (2)	H26C—C26—H26B	109.5
C13—C15—H15	120.5	C24—C26—H26A	109.5
C18—C15—H15	120.5	H26C—C26—H26A	109.5
C17—C16—C14	120.5 (2)	H26B—C26—H26A	109.5

C3—C1—C2—C4	−0.2 (3)	C13—N1—C19—C20	167.56 (16)
C20—C1—C2—C4	179.5 (2)	C9—C7—C19—O2	−13.9 (2)
C2—C1—C3—C6	1.2 (4)	C8—C7—C19—O2	172.30 (17)
C20—C1—C3—C6	−178.5 (2)	C9—C7—C19—N1	−136.22 (19)
C1—C2—C4—C5	−1.4 (4)	C8—C7—C19—N1	50.0 (2)
C2—C4—C5—C6	2.1 (4)	C9—C7—C19—C20	110.7 (2)
C2—C4—C5—F1	−178.5 (2)	C8—C7—C19—C20	−63.1 (2)
C4—C5—C6—C3	−1.1 (4)	C3—C1—C20—C21	19.1 (3)
F1—C5—C6—C3	179.5 (2)	C2—C1—C20—C21	−160.69 (19)
C1—C3—C6—C5	−0.6 (4)	C3—C1—C20—C19	−105.0 (2)
C9—C7—C8—C11	−2.1 (3)	C2—C1—C20—C19	75.2 (2)
C19—C7—C8—C11	171.8 (2)	O2—C19—C20—C1	34.5 (2)
C8—C7—C9—C10	2.3 (3)	N1—C19—C20—C1	152.52 (15)
C19—C7—C9—C10	−171.51 (19)	C7—C19—C20—C1	−87.0 (2)
C7—C9—C10—C12	−0.4 (3)	O2—C19—C20—C21	−95.51 (18)
C7—C8—C11—C12	0.0 (3)	N1—C19—C20—C21	22.51 (18)
C9—C10—C12—C11	−1.9 (4)	C7—C19—C20—C21	142.99 (15)
C9—C10—C12—F2	178.2 (2)	C1—C20—C21—C22	−142.77 (17)
C8—C11—C12—C10	2.1 (4)	C19—C20—C21—C22	−14.23 (19)
C8—C11—C12—F2	−178.0 (2)	C1—C20—C21—C23	101.3 (2)
C22—N1—C13—C15	−139.4 (2)	C19—C20—C21—C23	−130.18 (17)
C19—N1—C13—C15	27.3 (3)	C13—N1—C22—O1	3.7 (3)
C22—N1—C13—C14	41.9 (3)	C19—N1—C22—O1	−164.41 (18)
C19—N1—C13—C14	−151.38 (18)	C13—N1—C22—C21	−175.28 (16)
C15—C13—C14—C16	0.6 (3)	C19—N1—C22—C21	16.6 (2)
N1—C13—C14—C16	179.30 (19)	C20—C21—C22—O1	−179.48 (18)
C14—C13—C15—C18	−0.3 (3)	C23—C21—C22—O1	−58.8 (2)
N1—C13—C15—C18	−179.03 (19)	C20—C21—C22—N1	−0.5 (2)
C13—C14—C16—C17	−0.6 (3)	C23—C21—C22—N1	120.22 (17)
C14—C16—C17—C18	0.3 (4)	C22—C21—C23—O3	−85.3 (2)
C16—C17—C18—C15	−0.1 (4)	C20—C21—C23—O3	29.6 (3)
C13—C15—C18—C17	0.1 (4)	C22—C21—C23—C24	94.0 (2)
C22—N1—C19—O2	95.72 (18)	C20—C21—C23—C24	−151.10 (19)
C13—N1—C19—O2	−72.2 (2)	O3—C23—C24—C26	−88.0 (3)
C22—N1—C19—C7	−143.26 (17)	C21—C23—C24—C26	92.8 (3)
C13—N1—C19—C7	48.8 (2)	O3—C23—C24—C25	35.2 (3)
C22—N1—C19—C20	−24.53 (19)	C21—C23—C24—C25	−144.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱ	0.95	2.59	3.489 (3)	157
O2—H2···O1ⁱⁱ	0.84	1.93	2.7625 (18)	174

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₃F₂NO₃
M_r	435.45
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	153
a, b, c (Å)	24.506 (4), 10.2180 (15), 20.554 (3)
β (°)	121.963 (2)
V (Å³)	4366.5 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.15 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.986, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	10716, 4091, 2471
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.103, 1.02
No. of reflections	4091
No. of parameters	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱ	0.95	2.59	3.489 (3)	157
O2—H2···O1ⁱⁱ	0.84	1.93	2.7625 (18)	174

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

Acknowledgements

This work was supported by the Education Department of Zhejiang Province (No. Y200906515) and Zhejiang Gong Shang University (No. X-106).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1–19. CrossRef Web of Science Google Scholar
Baumann, K. L., Butler, D. E., Deering, C. F., Mennen, K. E., Millar, A., Nanninga, T. N., Palmer, C. W. & Roth, B. D. (1992). Tetrahedron Lett. 33, 2283–2284. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lea, A. P. & McTavish, D. (1997). Drugs, 53, 828–847. CrossRef CAS PubMed Web of Science Google Scholar
Sagyam, R. R., Vurimidi, H., Padi, P. R. & Ghanta, M. R. (2007). J. Heterocycl. Chem. 44, 923–926. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o873-o874

doi:10.1107/S1600536811008786

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4,5-Bis(4-fluoro­phen­yl)-5-hy­dr­oxy-3-(2-methyl­propano­yl)-1-phenyl­pyrrolidin-2-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,5-Bis(4-fluorophenyl)-5-hydroxy-3-(2-methylpropanoyl)-1-phenylpyrrolidin-2-one