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Acta Cryst. (2008). E64, o1548    [ doi:10.1107/S1600536808022265 ]

Degradation of atorvastatin: (1R,2S,4S,5S)-4-(4-fluorophenyl)-2-hydroperoxy-4-hydroxy-2-isopropyl-N,5-diphenyl-3,6-dioxabicyclo[3.1.0]hexane-1-carboxamide

M. Ashfaq, M. N. Tahir, I. U. Khan, M. S. Iqbal and M. N. Arshad

Abstract top

The degradation of atorvastatin calcium in methanol and hydrogen peroxide results in the crystallization of the title compound, C26H24FNO6, which shows several differences compared with the starting compound. In the crystal structure of the title compound, intra- and intermolecular hydrogen bonding is found.

Comment top

Atorvastatin calcium is widly used as synthetic lipid-lowering agent (Rouleau, 2005). The medicinal organic compounds are affected by the environment in which they are stored and produce degradation products through reactions with moisture (humidity) and oxygen in air (oxidation) or due to thermal shocks. Thus, all the drug substances are given an expiration date which is the time at which 10% of the initial amount of a drug is transformed to various degradation products (United States Pharmacopeia, 2007). Thus it is a standard practice to study the stability profile of a drug substance under stress. In order to simulate the air oxidation under accelerated conditions the products are subjected to the reaction with hydrogen peroxide. The purpose of this study was to see the reaction of atorvastatin calcium towards hydrogen peroxide. In this example, the title compound crystallized after the reaction at ambient temperature.

In the structure of the title compound, the central five-membered ring (O1/C1–C4) is in an envelope conformation, with the C1–C4 atoms in the plane (Fig. 1). The puckering parameters (Cremer & Pople, 1975) are Q = 0.9737 (16)Å, θ = 115.69 (10)° and φ = 0.10 (13)°. The dihedral angles between this ring and benzene rings C6–C11, C12–C17 and C18–C23 are 88.71 (11), 66.85 (11) and 64.39 (12)°, respectively. There is intramolecular O—H···O and N—H···O hydrogen bonding between N1 and O3, between O2 and O5 and between O5 and O6 (Fig. 1 and Table 1). In the crystal structure, the molecules are connected via intermolecular O—H···O and N—H···O hydrogen bonding (Table 1).

Related literature top

For related literature, see: Cremer & Pople (1975); Rouleau (2005); United States Pharmacopeia (2007).

Experimental top

Atorvastatin calcium (100 mg) was dissolved in methanol (25 ml) at room temperature. A separate solution (10 ml) of hydrogen peroxide (5%) was prepared in distilled water. Both the solutions were mixed togather and set aside for 2 months. The crystals suitable for x-ray diffraction of the title compound (I) were obtained by filteration.

Refinement top

The coordinates of H atoms attached with N1 and O2 were refined freely. The remaining H atoms were positioned with idealized geometry (O-H allowed to rotate but not to tip) with C—H = 0.93, 0.96 Å and O—H = 0.82 Å for aromatic, methyl and peroxide H, and were refined using a riding model with Uiso(H) = xUeq(C, N, O), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of the title compound, with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii. The dashed lines shows intramolecular H-bonding.
[Figure 2] Fig. 2. The formation of the title compound.
(1R,2S,4S,5S)-4-(4-fluorophenyl)- 2-hydroperoxy-4-hydroxy-2-isopropyl-N,5-diphenyl-3,6- dioxabicyclo[3.1.0]hexane-1-carboxamide top
Crystal data top
C26H24FNO6F000 = 976
Mr = 465.46Dx = 1.314 Mg m−3
Monoclinic, P21/nMo Kα radiation radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5340 reflections
a = 11.7560 (6) Åθ = 2.0–27.5º
b = 11.7489 (6) ŵ = 0.10 mm−1
c = 17.0889 (9) ÅT = 296 (2) K
β = 94.438 (2)ºPrismatic, colorless
V = 2353.2 (2) Å30.25 × 0.18 × 0.15 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer		5340 independent reflections
Radiation source: fine-focus sealed tube3008 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
Detector resolution: 7.50 pixels mm-1θmax = 27.5º
T = 296(2) Kθmin = 2.0º
ω scansh = −15→14
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −15→8
Tmin = 0.975, Tmax = 0.980l = −22→21
14754 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049  w = 1/[σ2(Fo2) + (0.0541P)2 + 0.5969P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.136(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.34 e Å−3
5340 reflectionsΔρmin = −0.27 e Å−3
318 parametersExtinction correction: emperical, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0032 (7)
Secondary atom site location: difference Fourier map
Crystal data top
C26H24FNO6V = 2353.2 (2) Å3
Mr = 465.46Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.7560 (6) ŵ = 0.10 mm−1
b = 11.7489 (6) ÅT = 296 (2) K
c = 17.0889 (9) Å0.25 × 0.18 × 0.15 mm
β = 94.438 (2)º
Data collection top
Bruker Kappa APEXII CCD
diffractometer		5340 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		3008 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.980Rint = 0.040
14754 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049318 parameters
wR(F2) = 0.136H atoms treated by a mixture of
independent and constrained refinement
S = 1.02Δρmax = 0.34 e Å−3
5340 reflectionsΔρmin = −0.27 e Å−3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
xyzUiso*/Ueq
F10.7275 (2)0.00876 (18)−0.10244 (10)0.1428 (12)
O10.91061 (11)0.21012 (11)0.21795 (7)0.0426 (5)
O20.78009 (12)0.35021 (11)0.17484 (8)0.0455 (5)
O30.75203 (11)0.07280 (10)0.26940 (7)0.0383 (4)
O40.96555 (12)0.28576 (11)0.34067 (8)0.0512 (5)
O50.88438 (14)0.38004 (12)0.33419 (9)0.0591 (6)
O60.78216 (14)0.25802 (13)0.43917 (8)0.0622 (6)
N10.70884 (15)0.07964 (14)0.42697 (10)0.0428 (6)
C10.79736 (16)0.23366 (15)0.18667 (11)0.0373 (6)
C20.72161 (16)0.18934 (14)0.24910 (11)0.0361 (6)
C30.79830 (16)0.16319 (15)0.31885 (11)0.0362 (6)
C40.91978 (17)0.19004 (16)0.30000 (11)0.0398 (6)
C50.76193 (17)0.17068 (16)0.40107 (11)0.0426 (7)
C60.66547 (17)0.06482 (18)0.50124 (11)0.0430 (7)
C70.64405 (19)−0.0442 (2)0.52493 (13)0.0545 (8)
C80.5989 (2)−0.0630 (3)0.59596 (16)0.0742 (10)
C90.5747 (2)0.0265 (3)0.64262 (15)0.0848 (13)
C100.5957 (3)0.1338 (3)0.61935 (17)0.0905 (14)
C110.6417 (2)0.1550 (2)0.54889 (15)0.0731 (10)
C120.60000 (17)0.22332 (16)0.24931 (12)0.0432 (7)
C130.56860 (19)0.31146 (18)0.29682 (14)0.0535 (8)
C140.4566 (2)0.3464 (2)0.29578 (17)0.0691 (10)
C150.3765 (2)0.2949 (2)0.2464 (2)0.0809 (13)
C160.4051 (2)0.2077 (3)0.1996 (2)0.0851 (13)
C170.5172 (2)0.1703 (2)0.20123 (15)0.0634 (9)
C180.77882 (17)0.17385 (16)0.10816 (11)0.0417 (7)
C190.6918 (2)0.2070 (2)0.05454 (13)0.0628 (9)
C200.6729 (3)0.1504 (3)−0.01611 (15)0.0865 (13)
C210.7429 (3)0.0629 (3)−0.03176 (16)0.0877 (13)
C220.8274 (3)0.0266 (2)0.01933 (17)0.0858 (13)
C230.8452 (2)0.08283 (19)0.09060 (14)0.0633 (9)
C241.00575 (18)0.09376 (19)0.31729 (13)0.0483 (8)
C251.1220 (2)0.1214 (2)0.28961 (16)0.0707 (10)
C261.0152 (2)0.0571 (2)0.40307 (14)0.0725 (10)
H10.7025 (18)0.0224 (18)0.3959 (12)0.0513*
H20.7978 (19)0.3806 (18)0.2186 (13)0.0546*
H50.842380.376580.370260.0709*
H70.65998−0.105450.493080.0653*
H80.58498−0.136980.612050.0891*
H90.543820.013700.690320.1016*
H100.578900.194490.651410.1082*
H110.656400.229240.533750.0877*
H130.623830.347620.329910.0642*
H140.436080.404710.328660.0830*
H150.301210.319690.244570.0971*
H160.349240.172910.166230.1022*
H170.536170.109560.169890.0761*
H190.645360.267900.065950.0754*
H200.613430.17187−0.052180.1038*
H220.87298−0.034690.007300.1031*
H230.902950.058410.126980.0760*
H240.9756 (19)0.0315 (18)0.2877 (12)0.0580*
H25A1.172690.058480.300930.1061*
H25B1.151920.188100.316280.1061*
H25C1.114870.135070.234060.1061*
H26A1.06946−0.003730.410360.1087*
H26B0.942050.031560.417370.1087*
H26C1.039990.120470.435540.1087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.231 (3)0.1278 (16)0.0649 (12)−0.0243 (16)−0.0177 (13)−0.0448 (11)
O10.0387 (8)0.0528 (8)0.0357 (8)−0.0054 (6)−0.0016 (6)0.0093 (6)
O20.0619 (10)0.0324 (7)0.0409 (8)−0.0028 (6)−0.0034 (7)0.0037 (6)
O30.0471 (8)0.0307 (6)0.0361 (7)−0.0042 (6)−0.0036 (6)0.0030 (5)
O40.0506 (9)0.0456 (8)0.0549 (9)−0.0083 (7)−0.0120 (7)−0.0004 (7)
O50.0700 (11)0.0434 (8)0.0632 (11)−0.0068 (8)0.0008 (8)−0.0020 (7)
O60.0906 (12)0.0504 (9)0.0464 (9)−0.0176 (8)0.0105 (8)−0.0098 (7)
N10.0522 (11)0.0422 (9)0.0347 (10)−0.0061 (8)0.0080 (8)−0.0016 (7)
C10.0396 (12)0.0348 (10)0.0362 (11)−0.0016 (8)−0.0044 (8)0.0063 (8)
C20.0416 (12)0.0293 (9)0.0364 (11)−0.0029 (8)−0.0024 (8)0.0022 (8)
C30.0414 (11)0.0322 (9)0.0339 (11)−0.0048 (8)−0.0032 (8)0.0015 (8)
C40.0437 (12)0.0412 (10)0.0329 (11)−0.0068 (9)−0.0064 (9)0.0042 (8)
C50.0492 (12)0.0423 (11)0.0357 (11)−0.0021 (9)−0.0004 (9)0.0002 (9)
C60.0379 (12)0.0577 (12)0.0334 (11)−0.0021 (10)0.0024 (9)0.0001 (10)
C70.0486 (13)0.0631 (14)0.0525 (14)0.0022 (11)0.0090 (11)0.0138 (11)
C80.0561 (16)0.103 (2)0.0640 (17)−0.0041 (14)0.0080 (13)0.0336 (16)
C90.0597 (18)0.156 (3)0.0398 (15)−0.0171 (19)0.0110 (12)0.0042 (18)
C100.087 (2)0.124 (3)0.0645 (19)−0.0228 (19)0.0319 (16)−0.0354 (18)
C110.0829 (19)0.0770 (17)0.0628 (17)−0.0140 (14)0.0274 (14)−0.0194 (14)
C120.0416 (12)0.0378 (10)0.0497 (12)−0.0045 (9)−0.0002 (10)0.0081 (9)
C130.0451 (14)0.0472 (12)0.0682 (16)0.0003 (10)0.0045 (11)0.0015 (11)
C140.0549 (16)0.0530 (14)0.101 (2)0.0052 (12)0.0171 (15)0.0081 (13)
C150.0405 (15)0.0652 (17)0.137 (3)0.0015 (13)0.0072 (16)0.0209 (18)
C160.0458 (16)0.0774 (19)0.128 (3)−0.0130 (14)−0.0190 (16)−0.0045 (18)
C170.0509 (15)0.0561 (14)0.0810 (18)−0.0072 (12)−0.0098 (12)−0.0047 (12)
C180.0531 (13)0.0367 (10)0.0343 (11)−0.0045 (9)−0.0031 (9)0.0058 (8)
C190.0784 (18)0.0555 (14)0.0507 (14)0.0011 (12)−0.0196 (12)0.0020 (11)
C200.120 (3)0.080 (2)0.0526 (17)−0.0065 (18)−0.0373 (16)−0.0018 (14)
C210.142 (3)0.0704 (19)0.0476 (16)−0.0215 (19)−0.0116 (18)−0.0167 (14)
C220.126 (3)0.0653 (17)0.0657 (19)0.0120 (17)0.0044 (18)−0.0192 (14)
C230.0869 (19)0.0527 (13)0.0489 (14)0.0085 (13)−0.0044 (12)−0.0052 (11)
C240.0447 (13)0.0498 (12)0.0488 (14)0.0012 (10)−0.0073 (10)0.0072 (10)
C250.0432 (14)0.0843 (18)0.0840 (19)0.0059 (12)0.0013 (13)0.0167 (14)
C260.0714 (17)0.0825 (18)0.0613 (16)0.0128 (14)−0.0092 (13)0.0265 (13)
Geometric parameters (Å, °) top
F1—C211.365 (3)C15—C161.358 (4)
O1—C11.423 (2)C16—C171.387 (3)
O1—C41.418 (2)C18—C191.376 (3)
O2—C11.397 (2)C18—C231.371 (3)
O3—C21.450 (2)C19—C201.381 (4)
O3—C31.438 (2)C20—C211.356 (5)
O4—O51.461 (2)C21—C221.340 (5)
O4—C41.407 (2)C22—C231.387 (4)
O6—C51.229 (2)C24—C251.516 (3)
O2—H20.84 (2)C24—C261.524 (3)
O5—H50.8200C7—H70.9300
N1—C51.331 (3)C8—H80.9300
N1—C61.415 (3)C9—H90.9300
N1—H10.86 (2)C10—H100.9300
C1—C181.515 (3)C11—H110.9300
C1—C21.533 (3)C13—H130.9300
C2—C31.470 (3)C14—H140.9300
C2—C121.485 (3)C15—H150.9300
C3—C41.521 (3)C16—H160.9300
C3—C51.503 (3)C17—H170.9300
C4—C241.530 (3)C19—H190.9300
C6—C111.378 (3)C20—H200.9300
C6—C71.373 (3)C22—H220.9300
C7—C81.380 (3)C23—H230.9300
C8—C91.363 (5)C24—H240.94 (2)
C9—C101.350 (5)C25—H25A0.9600
C10—C111.380 (4)C25—H25B0.9600
C12—C171.374 (3)C25—H25C0.9600
C12—C131.384 (3)C26—H26A0.9600
C13—C141.378 (3)C26—H26B0.9600
C14—C151.357 (4)C26—H26C0.9600
C1—O1—C4113.66 (14)C18—C19—C20120.5 (2)
C2—O3—C361.20 (11)C19—C20—C21118.6 (3)
O5—O4—C4110.25 (14)F1—C21—C20119.1 (3)
C1—O2—H2105.3 (14)F1—C21—C22118.0 (3)
O4—O5—H5109.00C20—C21—C22122.9 (3)
C5—N1—C6127.44 (17)C21—C22—C23118.3 (3)
C5—N1—H1116.4 (14)C18—C23—C22120.9 (2)
C6—N1—H1116.1 (14)C4—C24—C26113.12 (18)
O1—C1—C2104.45 (14)C25—C24—C26111.13 (19)
O1—C1—C18107.99 (15)C4—C24—C25112.29 (18)
O1—C1—O2111.48 (15)C6—C7—H7120.00
O2—C1—C2110.37 (15)C8—C7—H7120.00
O2—C1—C18108.49 (15)C7—C8—H8120.00
C2—C1—C18114.03 (15)C9—C8—H8120.00
O3—C2—C358.97 (11)C8—C9—H9120.00
O3—C2—C12118.22 (15)C10—C9—H9120.00
C1—C2—C3106.41 (15)C9—C10—H10119.00
O3—C2—C1109.96 (14)C11—C10—H10119.00
C1—C2—C12121.45 (16)C6—C11—H11120.00
C3—C2—C12125.76 (17)C10—C11—H11120.00
O3—C3—C5118.09 (15)C12—C13—H13120.00
C4—C3—C5121.71 (16)C14—C13—H13120.00
C2—C3—C4108.17 (15)C13—C14—H14120.00
C2—C3—C5123.01 (16)C15—C14—H14120.00
O3—C3—C259.83 (11)C14—C15—H15120.00
O3—C3—C4110.33 (15)C16—C15—H15120.00
O4—C4—C24105.89 (16)C15—C16—H16120.00
C3—C4—C24115.00 (16)C17—C16—H16120.00
O1—C4—C24108.21 (16)C12—C17—H17120.00
O1—C4—O4110.64 (15)C16—C17—H17120.00
O1—C4—C3104.07 (15)C18—C19—H19120.00
O4—C4—C3112.99 (15)C20—C19—H19120.00
O6—C5—N1124.85 (18)C19—C20—H20121.00
N1—C5—C3116.01 (16)C21—C20—H20121.00
O6—C5—C3119.15 (17)C21—C22—H22121.00
N1—C6—C11122.63 (19)C23—C22—H22121.00
C7—C6—C11119.54 (19)C18—C23—H23120.00
N1—C6—C7117.81 (18)C22—C23—H23120.00
C6—C7—C8120.1 (2)C4—C24—H24104.8 (14)
C7—C8—C9120.2 (3)C25—C24—H24108.0 (14)
C8—C9—C10119.8 (3)C26—C24—H24107.0 (13)
C9—C10—C11121.2 (3)C24—C25—H25A109.00
C6—C11—C10119.2 (2)C24—C25—H25B109.00
C2—C12—C13120.23 (18)C24—C25—H25C109.00
C2—C12—C17120.97 (18)H25A—C25—H25B110.00
C13—C12—C17118.8 (2)H25A—C25—H25C109.00
C12—C13—C14120.9 (2)H25B—C25—H25C109.00
C13—C14—C15119.4 (2)C24—C26—H26A109.00
C14—C15—C16120.7 (2)C24—C26—H26B109.00
C15—C16—C17120.4 (3)C24—C26—H26C109.00
C12—C17—C16119.8 (2)H26A—C26—H26B109.00
C19—C18—C23118.79 (19)H26A—C26—H26C109.00
C1—C18—C19120.47 (18)H26B—C26—H26C109.00
C1—C18—C23120.69 (18)
C4—O1—C1—O2100.71 (17)O3—C3—C4—O4173.71 (14)
C4—O1—C1—C2−18.48 (18)O3—C3—C4—C24−64.6 (2)
C4—O1—C1—C18−140.20 (15)C2—C3—C4—O1−10.10 (19)
C1—O1—C4—O4−103.48 (17)C2—C3—C4—O4109.97 (17)
C1—O1—C4—C318.17 (19)C2—C3—C4—C24−128.29 (17)
C1—O1—C4—C24140.93 (16)C5—C3—C4—O1−161.36 (16)
C3—O3—C2—C197.59 (16)C5—C3—C4—O4−41.3 (2)
C3—O3—C2—C12−116.82 (19)C5—C3—C4—C2480.5 (2)
C2—O3—C3—C4−99.75 (16)O3—C3—C5—O6−166.15 (17)
C2—O3—C3—C5113.84 (19)O3—C3—C5—N113.7 (3)
O5—O4—C4—O168.46 (18)C2—C3—C5—O6−95.6 (2)
O5—O4—C4—C3−47.78 (19)C2—C3—C5—N184.3 (2)
O5—O4—C4—C24−174.52 (14)C4—C3—C5—O651.4 (3)
C6—N1—C5—O60.3 (3)C4—C3—C5—N1−128.75 (19)
C6—N1—C5—C3−179.54 (18)O1—C4—C24—C2558.3 (2)
C5—N1—C6—C7−161.4 (2)O1—C4—C24—C26−174.90 (17)
C5—N1—C6—C1120.3 (3)O4—C4—C24—C25−60.3 (2)
O1—C1—C2—O3−51.65 (17)O4—C4—C24—C2666.5 (2)
O1—C1—C2—C310.65 (18)C3—C4—C24—C25174.17 (18)
O1—C1—C2—C12164.07 (15)C3—C4—C24—C26−59.1 (2)
O2—C1—C2—O3−171.59 (14)N1—C6—C7—C8−178.3 (2)
O2—C1—C2—C3−109.29 (16)C11—C6—C7—C80.1 (3)
O2—C1—C2—C1244.1 (2)N1—C6—C11—C10177.7 (2)
C18—C1—C2—O366.0 (2)C7—C6—C11—C10−0.6 (4)
C18—C1—C2—C3128.30 (16)C6—C7—C8—C90.4 (4)
C18—C1—C2—C12−78.3 (2)C7—C8—C9—C10−0.4 (4)
O1—C1—C18—C19−160.88 (18)C8—C9—C10—C11−0.1 (4)
O1—C1—C18—C2321.9 (2)C9—C10—C11—C60.6 (4)
O2—C1—C18—C19−39.9 (2)C2—C12—C13—C14177.9 (2)
O2—C1—C18—C23142.86 (19)C17—C12—C13—C14−0.5 (3)
C2—C1—C18—C1983.5 (2)C2—C12—C17—C16−176.6 (2)
C2—C1—C18—C23−93.7 (2)C13—C12—C17—C161.7 (4)
O3—C2—C3—C4103.43 (15)C12—C13—C14—C15−1.2 (4)
O3—C2—C3—C5−105.77 (18)C13—C14—C15—C161.7 (4)
C1—C2—C3—O3−103.78 (15)C14—C15—C16—C17−0.4 (5)
C1—C2—C3—C4−0.35 (19)C15—C16—C17—C12−1.3 (4)
C1—C2—C3—C5150.45 (16)C1—C18—C19—C20−178.2 (2)
C12—C2—C3—O3104.29 (19)C23—C18—C19—C20−0.9 (3)
C12—C2—C3—C4−152.28 (17)C1—C18—C23—C22179.0 (2)
C12—C2—C3—C5−1.5 (3)C19—C18—C23—C221.7 (3)
O3—C2—C12—C13121.7 (2)C18—C19—C20—C21−1.0 (4)
O3—C2—C12—C17−60.0 (3)C19—C20—C21—F1−177.8 (3)
C1—C2—C12—C13−96.8 (2)C19—C20—C21—C222.2 (5)
C1—C2—C12—C1781.5 (2)F1—C21—C22—C23178.6 (3)
C3—C2—C12—C1351.3 (3)C20—C21—C22—C23−1.4 (5)
C3—C2—C12—C17−130.4 (2)C21—C22—C23—C18−0.6 (4)
O3—C3—C4—O153.64 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.86 (2)2.36 (2)2.780 (2)110.8 (17)
N1—H1···O2i0.86 (2)2.37 (2)3.216 (2)168.0 (18)
O2—H2···O50.84 (2)2.15 (2)2.920 (2)152 (2)
O2—H2···O3ii0.84 (2)2.35 (2)2.8188 (18)116.1 (18)
O5—H5···O60.82001.99002.655 (2)138.00
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.86 (2)2.36 (2)2.780 (2)110.8 (17)
N1—H1···O2i0.86 (2)2.37 (2)3.216 (2)168.0 (18)
O2—H2···O50.84 (2)2.15 (2)2.920 (2)152 (2)
O2—H2···O3ii0.84 (2)2.35 (2)2.8188 (18)116.1 (18)
O5—H5···O60.82001.99002.655 (2)138.00
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2.
Acknowledgements top

MA greatfully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing him with a scholaship under the Indigenous PhD Program (PIN 042-120556-PS2-275).

references
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