rac-2-[2-(4-Fluoro-phen-yl)-2-oxo-1-phenyl-eth-yl]-4-methyl-3-oxo-N-phenyl-penta-namide.

The title compound, C(26)H(24)FNO(3), is a critical inter-mediate of a selective and competitive inhibitor of the enzyme 3-hy-droxy-3-methyl-glutaryl-coenzyme A (HMG-CoA) reductase. Inter-molecular N-H⋯O hydrogen bonding generates a chain along [give direction] that is the dominant inter-action in the crystal packing. Inter-molecular C-H⋯O inter-actions are also observed.

Related literature

For related structures, see: Baumann et al. (1992 ▶). For the title compound as an inter­mediate in the preparation of the HMG-CoA reductase inhibitor atorvastatin, see: Roth et al. (1991 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

C26H24FNO3

M = 417.46

Monoclinic,

a = 14.1694 (14) Å

b = 9.8307 (9) Å

c = 16.6367 (16) Å

β = 99.651 (2)°

V = 2284.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.15 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.990, T max = 0.996

10555 measured reflections

3792 independent reflections

2493 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.227

S = 1.06

3792 reflections

275 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.68 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046271/kp2271sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046271/kp2271Isup2.hkl

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

C26H24FNO3	F(000) = 880
Mr = 417.46	Dx = 1.214 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2549 reflections
a = 14.1694 (14) Å	θ = 2.4–21.8°
b = 9.8307 (9) Å	µ = 0.08 mm−1
c = 16.6367 (16) Å	T = 173 K
β = 99.651 (2)°	Prism, colourless
V = 2284.6 (4) Å3	0.15 × 0.10 × 0.05 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3792 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 24.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→15
Tmin = 0.990, Tmax = 0.996	k = −11→11
10555 measured reflections	l = −14→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1129P)2 + 1.1017P] where P = (Fo2 + 2Fc2)/3
3792 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.78 e Å−3
1 restraint	Δρmin = −0.68 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0713 (3)	0.2839 (5)	0.9806 (3)	0.0948 (13)
H1A	0.0361	0.2691	1.0236	0.114*
C2	0.0430 (3)	0.3814 (5)	0.9239 (3)	0.0996 (14)
H2A	−0.0107	0.4368	0.9286	0.120*
C3	0.0911 (2)	0.4006 (4)	0.8599 (2)	0.0769 (10)
H3A	0.0698	0.4674	0.8196	0.092*
C4	0.1710 (2)	0.3222 (3)	0.85420 (17)	0.0521 (7)
C5	0.2012 (3)	0.2269 (3)	0.9127 (2)	0.0763 (10)
H5A	0.2569	0.1745	0.9100	0.092*
C6	0.1503 (4)	0.2071 (4)	0.9758 (2)	0.0958 (14)
H6A	0.1705	0.1398	1.0159	0.115*
C7	0.2586 (2)	0.2567 (3)	0.74381 (17)	0.0499 (7)
C8	0.2898 (2)	0.3116 (3)	0.66692 (17)	0.0546 (7)
H8A	0.2728	0.4103	0.6617	0.066*
C9	0.2357 (2)	0.2362 (3)	0.59207 (18)	0.0617 (8)
H9A	0.2563	0.1388	0.5948	0.074*
C10	0.1280 (3)	0.2419 (4)	0.5882 (2)	0.0743 (10)
C11	0.0794 (4)	0.3651 (5)	0.5882 (3)	0.1127 (15)
H11A	0.1140	0.4482	0.5908	0.135*
C12	−0.0191 (4)	0.3675 (8)	0.5845 (4)	0.142 (2)
H12A	−0.0511	0.4524	0.5845	0.170*
C13	−0.0706 (5)	0.2506 (10)	0.5810 (4)	0.146 (2)
H13A	−0.1381	0.2531	0.5782	0.175*
C14	−0.0231 (5)	0.1283 (8)	0.5815 (3)	0.131 (2)
H14A	−0.0580	0.0456	0.5793	0.158*
C15	0.0746 (3)	0.1249 (5)	0.5851 (2)	0.0931 (12)
H15A	0.1059	0.0394	0.5855	0.112*
C16	0.3973 (2)	0.2978 (3)	0.6729 (2)	0.0695 (9)
C17	0.4603 (3)	0.3732 (5)	0.7404 (3)	0.1074 (10)
H17A	0.4183	0.4299	0.7697	0.129*
C18	0.5129 (5)	0.2730 (6)	0.8006 (4)	0.168 (3)
H18A	0.5533	0.3225	0.8447	0.253*
H18B	0.5531	0.2142	0.7728	0.253*
H18C	0.4665	0.2173	0.8234	0.253*
C19	0.5271 (3)	0.4666 (5)	0.7060 (3)	0.1074 (10)
H19A	0.5669	0.5158	0.7505	0.161*
H19B	0.4898	0.5319	0.6690	0.161*
H19C	0.5681	0.4133	0.6759	0.161*
C20	0.2594 (3)	0.2989 (3)	0.5144 (2)	0.0752 (10)
C21	0.2747 (2)	0.2140 (3)	0.44349 (17)	0.0595 (8)
C22	0.2713 (2)	0.0741 (3)	0.44226 (19)	0.0632 (8)
H22A	0.2592	0.0261	0.4890	0.076*
C23	0.2853 (3)	0.0031 (4)	0.3737 (2)	0.0784 (10)
H23A	0.2820	−0.0934	0.3725	0.094*
C24	0.3038 (3)	0.0743 (4)	0.3080 (2)	0.0821 (11)
C25	0.3089 (3)	0.2124 (4)	0.3068 (2)	0.0882 (11)
H25A	0.3221	0.2593	0.2600	0.106*
C26	0.2945 (3)	0.2819 (4)	0.3749 (2)	0.0776 (10)
H26A	0.2980	0.3784	0.3754	0.093*
N1	0.21798 (16)	0.3485 (2)	0.78690 (14)	0.0535 (6)
H1	0.2207	0.4340	0.7719	0.066 (9)*
O1	0.26887 (16)	0.13615 (19)	0.76232 (13)	0.0648 (6)
O2	0.2615 (3)	0.4226 (3)	0.50929 (17)	0.1281 (13)
O3	0.4304 (2)	0.2291 (3)	0.62480 (19)	0.1088 (11)
F1	0.3192 (2)	0.0052 (3)	0.24109 (15)	0.1311 (11)

	U11	U22	U33	U12	U13	U23
C1	0.107 (3)	0.106 (3)	0.087 (3)	−0.021 (3)	0.061 (3)	−0.016 (3)
C2	0.066 (2)	0.147 (4)	0.092 (3)	0.020 (2)	0.032 (2)	−0.018 (3)
C3	0.069 (2)	0.094 (3)	0.071 (2)	0.0213 (19)	0.0209 (17)	−0.0039 (19)
C4	0.0572 (17)	0.0468 (15)	0.0567 (17)	−0.0004 (13)	0.0220 (13)	−0.0059 (13)
C5	0.106 (3)	0.0581 (19)	0.075 (2)	0.0208 (18)	0.045 (2)	0.0083 (17)
C6	0.160 (4)	0.064 (2)	0.080 (3)	0.010 (2)	0.066 (3)	0.0072 (19)
C7	0.0563 (16)	0.0431 (16)	0.0535 (16)	−0.0041 (12)	0.0186 (13)	−0.0047 (12)
C8	0.0694 (19)	0.0447 (15)	0.0550 (17)	−0.0097 (13)	0.0256 (14)	−0.0043 (13)
C9	0.089 (2)	0.0455 (16)	0.0534 (17)	−0.0118 (15)	0.0210 (15)	−0.0043 (13)
C10	0.086 (2)	0.080 (2)	0.0550 (19)	−0.017 (2)	0.0062 (16)	0.0002 (16)
C11	0.095 (3)	0.098 (3)	0.139 (4)	0.002 (3)	0.001 (3)	0.005 (3)
C12	0.087 (4)	0.169 (6)	0.163 (6)	0.025 (4)	0.003 (3)	0.013 (4)
C13	0.090 (4)	0.215 (8)	0.125 (5)	−0.029 (5)	0.001 (3)	0.002 (5)
C14	0.107 (4)	0.173 (6)	0.113 (4)	−0.059 (4)	0.015 (3)	0.000 (4)
C15	0.103 (3)	0.101 (3)	0.077 (2)	−0.038 (2)	0.018 (2)	−0.002 (2)
C16	0.077 (2)	0.067 (2)	0.073 (2)	−0.0159 (17)	0.0366 (18)	−0.0126 (17)
C17	0.098 (2)	0.116 (2)	0.111 (2)	−0.0421 (18)	0.0240 (18)	−0.0169 (19)
C18	0.165 (6)	0.151 (6)	0.163 (6)	0.002 (4)	−0.051 (5)	0.006 (4)
C19	0.098 (2)	0.116 (2)	0.111 (2)	−0.0421 (18)	0.0240 (18)	−0.0169 (19)
C20	0.117 (3)	0.0525 (19)	0.061 (2)	−0.0195 (18)	0.0282 (19)	−0.0035 (15)
C21	0.070 (2)	0.0604 (19)	0.0477 (16)	−0.0125 (15)	0.0091 (14)	−0.0014 (14)
C22	0.071 (2)	0.061 (2)	0.0578 (18)	−0.0119 (15)	0.0107 (15)	−0.0049 (15)
C23	0.096 (3)	0.068 (2)	0.072 (2)	−0.0158 (19)	0.0166 (19)	−0.0157 (18)
C24	0.097 (3)	0.096 (3)	0.055 (2)	−0.012 (2)	0.0169 (18)	−0.025 (2)
C25	0.121 (3)	0.095 (3)	0.051 (2)	−0.015 (2)	0.0210 (19)	−0.0007 (19)
C26	0.112 (3)	0.068 (2)	0.0532 (19)	−0.0108 (19)	0.0178 (18)	0.0008 (16)
N1	0.0659 (15)	0.0405 (13)	0.0598 (14)	0.0020 (11)	0.0268 (12)	0.0001 (11)
O1	0.0940 (16)	0.0417 (12)	0.0663 (13)	0.0069 (10)	0.0355 (11)	0.0004 (9)
O2	0.261 (4)	0.0547 (16)	0.0844 (19)	−0.0303 (19)	0.076 (2)	−0.0051 (13)
O3	0.0924 (19)	0.129 (2)	0.121 (2)	−0.0246 (17)	0.0629 (18)	−0.0555 (19)
F1	0.195 (3)	0.128 (2)	0.0799 (16)	−0.0225 (19)	0.0503 (17)	−0.0418 (15)

C1—C2	1.357 (6)	C14—C15	1.376 (7)
C1—C6	1.363 (6)	C14—H14A	0.9500
C1—H1A	0.9500	C15—H15A	0.9500
C2—C3	1.370 (5)	C16—O3	1.201 (4)
C2—H2A	0.9500	C16—C17	1.507 (6)
C3—C4	1.387 (4)	C17—C19	1.499 (6)
C3—H3A	0.9500	C17—C18	1.509 (7)
C4—C5	1.366 (4)	C17—H17A	1.0000
C4—N1	1.419 (3)	C18—H18A	0.9800
C5—C6	1.383 (5)	C18—H18B	0.9800
C5—H5A	0.9500	C18—H18C	0.9800
C6—H6A	0.9500	C19—H19A	0.9800
C7—O1	1.227 (3)	C19—H19B	0.9800
C7—N1	1.341 (3)	C19—H19C	0.9800
C7—C8	1.521 (4)	C20—O2	1.220 (4)
C8—C16	1.516 (5)	C20—C21	1.490 (4)
C8—C9	1.539 (4)	C21—C22	1.375 (4)
C8—H8A	1.0000	C21—C26	1.390 (4)
C9—C10	1.517 (5)	C22—C23	1.379 (4)
C9—C20	1.520 (4)	C22—H22A	0.9500
C9—H9A	1.0000	C23—C24	1.361 (5)
C10—C15	1.372 (5)	C23—H23A	0.9500
C10—C11	1.394 (6)	C24—F1	1.352 (4)
C11—C12	1.387 (7)	C24—C25	1.360 (6)
C11—H11A	0.9500	C25—C26	1.368 (5)
C12—C13	1.357 (8)	C25—H25A	0.9500
C12—H12A	0.9500	C26—H26A	0.9500
C13—C14	1.377 (8)	N1—H1	0.8800
C13—H13A	0.9500
C2—C1—C6	120.0 (3)	C10—C15—C14	121.7 (5)
C2—C1—H1A	120.0	C10—C15—H15A	119.2
C6—C1—H1A	120.0	C14—C15—H15A	119.2
C1—C2—C3	120.7 (4)	O3—C16—C17	121.6 (4)
C1—C2—H2A	119.7	O3—C16—C8	120.4 (3)
C3—C2—H2A	119.7	C17—C16—C8	118.0 (3)
C2—C3—C4	119.7 (4)	C19—C17—C16	110.4 (4)
C2—C3—H3A	120.2	C19—C17—C18	112.4 (5)
C4—C3—H3A	120.2	C16—C17—C18	109.8 (4)
C5—C4—C3	119.6 (3)	C19—C17—H17A	108.0
C5—C4—N1	123.7 (3)	C16—C17—H17A	108.0
C3—C4—N1	116.7 (3)	C18—C17—H17A	108.0
C4—C5—C6	119.8 (3)	C17—C18—H18A	109.5
C4—C5—H5A	120.1	C17—C18—H18B	109.5
C6—C5—H5A	120.1	H18A—C18—H18B	109.5
C1—C6—C5	120.3 (4)	C17—C18—H18C	109.5
C1—C6—H6A	119.9	H18A—C18—H18C	109.5
C5—C6—H6A	119.9	H18B—C18—H18C	109.5
O1—C7—N1	124.0 (2)	C17—C19—H19A	109.5
O1—C7—C8	121.0 (2)	C17—C19—H19B	109.5
N1—C7—C8	115.0 (2)	H19A—C19—H19B	109.5
C16—C8—C7	110.1 (3)	C17—C19—H19C	109.5
C16—C8—C9	111.7 (2)	H19A—C19—H19C	109.5
C7—C8—C9	109.5 (2)	H19B—C19—H19C	109.5
C16—C8—H8A	108.5	O2—C20—C21	119.7 (3)
C7—C8—H8A	108.5	O2—C20—C9	118.3 (3)
C9—C8—H8A	108.5	C21—C20—C9	121.9 (3)
C10—C9—C20	108.3 (3)	C22—C21—C26	118.6 (3)
C10—C9—C8	112.2 (3)	C22—C21—C20	124.2 (3)
C20—C9—C8	110.0 (2)	C26—C21—C20	117.2 (3)
C10—C9—H9A	108.8	C21—C22—C23	120.6 (3)
C20—C9—H9A	108.8	C21—C22—H22A	119.7
C8—C9—H9A	108.8	C23—C22—H22A	119.7
C15—C10—C11	117.3 (4)	C24—C23—C22	118.5 (3)
C15—C10—C9	121.0 (4)	C24—C23—H23A	120.7
C11—C10—C9	121.7 (3)	C22—C23—H23A	120.7
C12—C11—C10	120.5 (5)	F1—C24—C25	118.3 (3)
C12—C11—H11A	119.7	F1—C24—C23	118.8 (4)
C10—C11—H11A	119.7	C25—C24—C23	122.9 (3)
C13—C12—C11	121.2 (6)	C24—C25—C26	118.1 (3)
C13—C12—H12A	119.4	C24—C25—H25A	121.0
C11—C12—H12A	119.4	C26—C25—H25A	121.0
C12—C13—C14	118.7 (6)	C25—C26—C21	121.3 (3)
C12—C13—H13A	120.7	C25—C26—H26A	119.4
C14—C13—H13A	120.7	C21—C26—H26A	119.4
C15—C14—C13	120.6 (6)	C7—N1—C4	126.8 (2)
C15—C14—H14A	119.7	C7—N1—H1	116.6
C13—C14—H14A	119.7	C4—N1—H1	116.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.10	2.959 (2)	178 (4)
C1—H1A···O3ii	0.95	2.43	3.371 (5)	169
C5—H5A···O1	0.95	2.52	2.963 (4)	109
C26—H26A···O2	0.95	2.41	2.735 (4)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.10	2.959 (2)	178 (4)
C1—H1A⋯O3ii	0.95	2.43	3.371 (5)	169

Symmetry codes: (i) ; (ii) .