tert-Butyl 2-(6-{2-[2-(4-fluoro­phen­yl)-5-isopropyl-3-phenyl-4-(phenyl­carbamo­yl)pyrrol-1-yl]eth­yl}-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Ya-Ming Wu

doi:10.1107/S160053681302624X

. 2013 Oct 9;69(Pt 11):o1621. doi: 10.1107/S160053681302624X

tert-Butyl 2-(6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Ya-Ming Wu ^a,^*

PMCID: PMC3884295 PMID: 24454071

Abstract

The title compound, C₄₀H₄₇FN₂O₅, crystallizes with two independent but similar molecules in the asymmetric unit. In the crystal, molecules are linked into chains along [100] by intermolecular N—H⋯O hydrogen bonds.

Related literature

For applications of the title compound, see: Zhang et al. (2012 ▶). For the synthesis, see: Zhang et al. (2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). graphic file with name e-69-o1621-scheme1.jpg

Experimental

Crystal data

C₄₀H₄₇FN₂O₅
M _r = 654.79
Monoclinic,
a = 13.439 (3) Å
b = 15.636 (3) Å
c = 18.644 (4) Å
β = 108.60 (3)°
V = 3713.1 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.976, T _max = 0.992
7418 measured reflections
7100 independent reflections
3663 reflections with I > 2σ(I)
R _int = 0.099
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.104
S = 1.00
7100 reflections
865 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681302624X/vm2197sup1.cif

e-69-o1621-sup1.cif^{(49.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302624X/vm2197Isup2.hkl

e-69-o1621-Isup2.hkl^{(347.4KB, hkl)}

Click here for additional data file.^{(13KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681302624X/vm2197Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.05	2.899 (7)	168
N4—H4A⋯O7ⁱⁱ	0.86	2.07	2.914 (7)	168

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Center of Test and Analysis, Nanjing University, for support.

supplementary crystallographic information

1. Comment

The title compound, (I), is an intermediate for the preparation of atorvastatin (Zhang et al., 2012). We herein report its molecular and crystal structure (Fig. 1). The asymmetric unit of the title compound, C₄₀H₄₇FN₂O₅, contains two independent molecules with similar structure (r.m.s. deviation 0.357 Å). The bond lengths and angles are within normal ranges (Allen et al., 1987). The dihedral angles between the aromatic rings are: 52.1 (3)° (A/B), 51.2 (3)° (A/C), 86.5 (3)° (A,D), 48.3 (3)° (E/F), 57.1 (3)° (E/G) and 54.4 (4)° (E,H) [with the rings defined as: A =N1/C15—C18, B=C22—C27, C=C28—C33, D=C35—C40, E=N3/C55—C58, F=C62—C67, G=C68—C73 and H=C75—C80].

In the crystal packing, the molecules are linked into chains by intermolecular N—H···O hydrogen bonds (Fig. 2 and Table 1).

2. Experimental

The title compound was synthesized according to a procedure published by Zhang et al. (2012). Crystals suitable for X-ray analysis were obtained by dissolving the compound (0.5 g) in ethanol (80 ml) and evaporating the solvent slowly at room temperature for about 5 d.