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

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ISSN: 2056-9890

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

aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, No. 625 Geguan Road, Dachang, Nanjing 210048, People's Republic of China
*Correspondence e-mail: adsony05@163.com

(Received 28 July 2013; accepted 23 September 2013; online 9 October 2013)

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[Zhang, Z., Mei, G., Fang, Z., Meng, X. & Wu, J. (2012). Patent CN 102766136.]). For the synthesis, see: Zhang et al. (2012[Zhang, Z., Mei, G., Fang, Z., Meng, X. & Wu, J. (2012). Patent CN 102766136.]). For standard bond lengths, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C40H47FN2O5

  • Mr = 654.79

  • Monoclinic, P 21

  • 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[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.976, Tmax = 0.992

  • 7418 measured reflections

  • 7100 independent reflections

  • 3663 reflections with I > 2σ(I)

  • Rint = 0.099

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.104

  • S = 1.00

  • 7100 reflections

  • 865 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93, 0.96, 0.97 and 0.98 Å for aromatic, methyl, methylene and methine H, respectively, and N—H = 0.86 Å and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C/N), where x = 1.5 for methyl H and x = 1.2 for other H atoms.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of (I) showing N—H···O hydrogen bonds as broken lines.
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 top
Crystal data top
C40H47FN2O5F(000) = 1400
Mr = 654.79Dx = 1.171 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 13.439 (3) Åθ = 9–13°
b = 15.636 (3) ŵ = 0.08 mm1
c = 18.644 (4) ÅT = 293 K
β = 108.60 (3)°Block, white
V = 3713.1 (13) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
3663 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.099
Graphite monochromatorθmax = 25.4°, θmin = 1.2°
ω/2θ scansh = 016
Absorption correction: ψ scan
(North et al., 1968)
k = 018
Tmin = 0.976, Tmax = 0.992l = 2221
7418 measured reflections3 standard reflections every 200 reflections
7100 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.026P)2]
where P = (Fo2 + 2Fc2)/3
7100 reflections(Δ/σ)max < 0.001
865 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.22 e Å3
Crystal data top
C40H47FN2O5V = 3713.1 (13) Å3
Mr = 654.79Z = 4
Monoclinic, P21Mo Kα radiation
a = 13.439 (3) ŵ = 0.08 mm1
b = 15.636 (3) ÅT = 293 K
c = 18.644 (4) Å0.30 × 0.20 × 0.10 mm
β = 108.60 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
3663 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.099
Tmin = 0.976, Tmax = 0.9923 standard reflections every 200 reflections
7418 measured reflections intensity decay: 1%
7100 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0591 restraint
wR(F2) = 0.104H-atom parameters constrained
S = 1.00Δρmax = 0.19 e Å3
7100 reflectionsΔρmin = 0.22 e Å3
865 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
xyzUiso*/Ueq
O10.3130 (3)0.1418 (3)0.0666 (2)0.0597 (12)
O20.2185 (3)0.2258 (3)0.0277 (3)0.0654 (13)
O30.4393 (3)0.1809 (3)0.04862 (19)0.0487 (10)
O40.5975 (3)0.1890 (3)0.07450 (19)0.0478 (10)
O51.0683 (4)0.5083 (3)0.0990 (3)0.0874 (17)
F10.8952 (4)0.2611 (4)0.3190 (2)0.135 (2)
N10.9191 (3)0.2897 (3)0.0191 (2)0.0423 (12)
N21.1740 (3)0.3936 (3)0.0966 (2)0.0478 (13)
H2A1.18430.34100.08290.057*
C10.1358 (6)0.1115 (5)0.0672 (5)0.094 (3)
H1A0.15530.14130.11470.141*
H1B0.08740.06650.06780.141*
H1C0.10320.15060.02690.141*
C20.2826 (6)0.0125 (5)0.1190 (4)0.100 (3)
H2B0.29580.04080.16680.150*
H2C0.34780.00690.11390.150*
H2D0.23730.03560.11640.150*
C30.2115 (7)0.0333 (5)0.0202 (4)0.103 (3)
H3A0.17920.07380.05940.154*
H3B0.16610.01520.02470.154*
H3C0.27720.01480.02510.154*
C40.2304 (5)0.0744 (5)0.0554 (4)0.061 (2)
C50.2986 (5)0.2099 (5)0.0224 (4)0.0535 (17)
C60.3943 (4)0.2655 (4)0.0431 (3)0.0546 (17)
H6A0.41480.27990.09640.066*
H6B0.37920.31810.01410.066*
C70.4842 (4)0.2174 (4)0.0262 (3)0.0528 (15)
H7A0.50980.17150.06330.063*
C80.5747 (4)0.2756 (4)0.0265 (3)0.0616 (19)
H8A0.60950.29630.07740.074*
H8B0.54850.32450.00600.074*
C90.6524 (4)0.2260 (4)0.0017 (3)0.0492 (14)
H9A0.68490.18060.03430.059*
C100.5113 (4)0.1363 (4)0.0759 (3)0.0480 (16)
C110.4506 (5)0.1194 (4)0.1593 (3)0.068 (2)
H11A0.42790.17280.18470.102*
H11B0.39060.08440.16300.102*
H11C0.49540.09050.18260.102*
C120.5434 (5)0.0525 (4)0.0337 (4)0.0650 (19)
H12A0.58020.06410.01860.098*
H12B0.58840.02130.05530.098*
H12C0.48190.01920.03770.098*
C130.7365 (4)0.2839 (4)0.0124 (3)0.0539 (17)
H13A0.70480.32270.05400.065*
H13B0.76540.31810.03290.065*
C140.8245 (4)0.2362 (4)0.0284 (3)0.0472 (16)
H14A0.84380.18750.00540.057*
H14B0.79970.21450.07980.057*
C150.9849 (4)0.3189 (4)0.0499 (3)0.0415 (15)
C161.0570 (4)0.3730 (4)0.0355 (3)0.0425 (15)
C171.0329 (4)0.3779 (4)0.0437 (3)0.0393 (15)
C180.9474 (4)0.3272 (4)0.0769 (3)0.0426 (15)
C190.8945 (5)0.3015 (5)0.1576 (3)0.0567 (19)
H19A0.81940.29490.16500.068*
C200.9351 (6)0.2165 (5)0.1756 (4)0.088 (3)
H20A0.92690.17380.14090.132*
H20B1.00810.22180.17100.132*
H20C0.89610.19990.22640.132*
C210.9067 (6)0.3704 (6)0.2135 (3)0.094 (3)
H21A0.87320.35130.26450.141*
H21B0.97990.38020.20580.141*
H21C0.87450.42270.20510.141*
C220.9649 (4)0.3015 (4)0.1220 (3)0.0466 (15)
C230.9530 (4)0.2195 (4)0.1472 (3)0.0510 (16)
H23A0.96220.17270.11920.061*
C240.9282 (5)0.2059 (5)0.2119 (3)0.0624 (19)
H24A0.91720.15080.22670.075*
C250.9201 (6)0.2743 (6)0.2539 (4)0.076 (2)
C260.9361 (6)0.3550 (5)0.2344 (4)0.085 (3)
H26A0.93170.40060.26540.102*
C270.9590 (5)0.3699 (5)0.1683 (3)0.0634 (19)
H27A0.97030.42540.15470.076*
C281.1479 (4)0.4110 (4)0.0935 (3)0.0413 (15)
C291.2151 (5)0.3607 (5)0.1487 (3)0.0600 (19)
H29A1.20210.30230.14870.072*
C301.3012 (5)0.3941 (5)0.2041 (3)0.0617 (19)
H30A1.34420.35850.24100.074*
C311.3229 (5)0.4797 (5)0.2044 (4)0.064 (2)
H31A1.37970.50310.24190.077*
C321.2592 (6)0.5301 (5)0.1483 (4)0.076 (2)
H32A1.27440.58790.14650.091*
C331.1727 (5)0.4959 (4)0.0944 (4)0.066 (2)
H33A1.12990.53170.05760.079*
C341.0917 (5)0.4326 (4)0.0816 (3)0.0473 (16)
C351.2448 (5)0.4279 (4)0.1317 (3)0.0461 (16)
C361.2423 (5)0.5113 (5)0.1550 (3)0.065 (2)
H36A1.19270.54880.14750.078*
C371.3131 (6)0.5401 (5)0.1895 (4)0.083 (2)
H37A1.31080.59690.20470.099*
C381.3866 (6)0.4863 (6)0.2018 (5)0.092 (3)
H38A1.43320.50550.22600.111*
C391.3895 (6)0.4029 (6)0.1773 (4)0.098 (3)
H39A1.43940.36570.18450.118*
C401.3187 (5)0.3728 (4)0.1416 (3)0.0638 (17)
H40A1.32200.31650.12490.077*
F20.6114 (4)0.3625 (4)0.1940 (2)0.1283 (19)
O61.2025 (3)0.4521 (3)0.4415 (2)0.0669 (13)
O71.2878 (4)0.3828 (3)0.5494 (3)0.0745 (14)
O81.0404 (3)0.4435 (3)0.5251 (2)0.0538 (11)
O90.8805 (3)0.4336 (3)0.5485 (2)0.0569 (12)
O100.4265 (4)0.0903 (3)0.5996 (3)0.0900 (18)
N30.5953 (3)0.3064 (3)0.5323 (2)0.0428 (12)
N40.3355 (4)0.2088 (3)0.6058 (2)0.0492 (13)
H4A0.32920.26230.59440.059*
C411.3828 (6)0.4827 (5)0.4474 (6)0.117 (3)
H41A1.41200.44530.48970.176*
H41B1.43160.52790.44850.176*
H41C1.36920.45110.40110.176*
C421.2913 (6)0.5694 (5)0.5232 (4)0.082 (2)
H42A1.32230.53320.56610.123*
H42B1.22320.58770.52330.123*
H42C1.33520.61850.52570.123*
C431.2291 (7)0.5774 (6)0.3827 (4)0.119 (3)
H43A1.16360.59900.38550.178*
H43B1.21670.54430.33730.178*
H43C1.27480.62440.38200.178*
C441.2807 (6)0.5207 (5)0.4518 (5)0.075 (2)
C451.2134 (5)0.3901 (4)0.4930 (4)0.0551 (18)
C461.1176 (5)0.3347 (4)0.4751 (3)0.0635 (19)
H46A1.13830.27500.47930.076*
H46B1.07340.34510.42350.076*
C471.0569 (4)0.3533 (4)0.5286 (3)0.0492 (14)
H47A1.09900.33700.58010.059*
C480.9528 (4)0.3085 (4)0.5073 (3)0.0550 (17)
H48A0.96420.24760.51620.066*
H48B0.91640.31680.45380.066*
C490.8848 (4)0.3417 (4)0.5527 (3)0.0536 (15)
H49A0.91360.32330.60560.064*
C500.9811 (5)0.4750 (5)0.5716 (4)0.0564 (18)
C510.9610 (6)0.5689 (5)0.5535 (4)0.087 (2)
H51A0.92250.57560.50080.130*
H51B1.02680.59850.56500.130*
H51C0.92110.59220.58340.130*
C521.0377 (5)0.4627 (5)0.6544 (3)0.088 (3)
H52A1.05110.40290.66480.133*
H52B0.99510.48410.68320.133*
H52C1.10310.49330.66830.133*
C530.7731 (4)0.3105 (4)0.5189 (4)0.067 (2)
H53A0.75250.31710.46440.080*
H53B0.77140.24990.52950.080*
C540.6933 (4)0.3548 (4)0.5465 (3)0.0475 (16)
H54A0.72340.36480.60050.057*
H54B0.67740.41010.52190.057*
C550.5303 (4)0.2801 (4)0.4605 (3)0.0438 (15)
C560.4548 (4)0.2267 (4)0.4725 (3)0.0434 (15)
C570.4755 (4)0.2202 (4)0.5526 (3)0.0456 (16)
C580.5604 (4)0.2695 (4)0.5878 (3)0.0426 (15)
C590.6099 (5)0.2903 (4)0.6695 (3)0.0544 (17)
H59A0.68560.29520.67850.065*
C600.5715 (6)0.3788 (5)0.6877 (4)0.098 (3)
H60A0.58290.42100.65380.146*
H60B0.60970.39430.73890.146*
H60C0.49790.37570.68170.146*
C610.5949 (5)0.2228 (5)0.7231 (3)0.080 (2)
H61A0.62830.24100.77430.120*
H61B0.62550.17000.71430.120*
H61C0.52120.21470.71460.120*
C620.5473 (4)0.3040 (4)0.3898 (3)0.0438 (15)
C630.5648 (4)0.3885 (4)0.3714 (3)0.0481 (15)
H63A0.56090.43220.40420.058*
C640.5872 (5)0.4090 (5)0.3073 (3)0.0617 (19)
H64A0.60070.46530.29700.074*
C650.5893 (6)0.3445 (6)0.2586 (4)0.077 (2)
C660.5680 (6)0.2596 (6)0.2715 (4)0.081 (2)
H66A0.56800.21700.23670.097*
C670.5470 (5)0.2406 (5)0.3373 (3)0.064 (2)
H67A0.53240.18440.34690.076*
C680.3636 (5)0.1904 (4)0.4129 (3)0.0460 (16)
C690.2946 (5)0.2440 (4)0.3621 (3)0.0582 (19)
H69A0.30520.30280.36630.070*
C700.2103 (5)0.2119 (5)0.3053 (4)0.073 (2)
H70A0.16640.24910.27030.088*
C710.1900 (5)0.1250 (5)0.2995 (4)0.069 (2)
H71A0.13280.10330.26130.083*
C720.2570 (5)0.0709 (5)0.3520 (4)0.088 (3)
H72A0.24420.01240.34900.106*
C730.3423 (6)0.1024 (4)0.4086 (4)0.075 (2)
H73A0.38570.06540.44400.090*
C740.4107 (5)0.1659 (4)0.5892 (3)0.0488 (16)
C750.2655 (5)0.1746 (5)0.6406 (3)0.0581 (19)
C760.2330 (5)0.0916 (5)0.6325 (4)0.079 (2)
H76A0.25750.05410.60320.095*
C770.1621 (8)0.0630 (7)0.6688 (6)0.130 (4)
H77A0.13700.00710.66220.156*
C780.1306 (8)0.1185 (8)0.7140 (6)0.129 (4)
H78A0.08540.09920.73940.155*
C790.1634 (6)0.2008 (7)0.7228 (4)0.099 (3)
H79A0.13890.23780.75260.119*
C800.2318 (5)0.2296 (4)0.6884 (3)0.0667 (18)
H80A0.25660.28540.69620.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.054 (3)0.057 (3)0.076 (3)0.001 (2)0.032 (2)0.011 (3)
O20.052 (3)0.057 (3)0.089 (3)0.001 (2)0.024 (2)0.008 (3)
O30.045 (2)0.056 (3)0.047 (2)0.000 (2)0.0183 (19)0.005 (2)
O40.043 (2)0.054 (3)0.052 (2)0.008 (2)0.0231 (18)0.007 (2)
O50.098 (4)0.051 (3)0.143 (5)0.026 (3)0.080 (4)0.045 (3)
F10.181 (5)0.182 (5)0.072 (3)0.043 (4)0.082 (3)0.012 (3)
N10.040 (3)0.049 (3)0.043 (3)0.009 (2)0.020 (2)0.002 (3)
N20.046 (3)0.042 (3)0.063 (3)0.002 (3)0.027 (3)0.008 (3)
C10.082 (5)0.072 (6)0.158 (8)0.004 (5)0.079 (6)0.011 (5)
C20.111 (7)0.077 (6)0.130 (7)0.003 (5)0.065 (6)0.029 (6)
C30.129 (8)0.075 (6)0.100 (6)0.010 (6)0.028 (6)0.010 (6)
C40.049 (4)0.044 (4)0.094 (5)0.009 (4)0.026 (4)0.004 (4)
C50.046 (4)0.052 (5)0.068 (4)0.002 (4)0.026 (3)0.000 (4)
C60.052 (4)0.061 (5)0.056 (4)0.010 (4)0.024 (3)0.010 (3)
C70.043 (3)0.060 (4)0.062 (4)0.007 (3)0.026 (3)0.001 (3)
C80.043 (3)0.085 (5)0.062 (4)0.020 (4)0.024 (3)0.025 (4)
C90.043 (3)0.064 (4)0.040 (3)0.015 (3)0.013 (3)0.005 (3)
C100.038 (3)0.053 (4)0.057 (4)0.005 (3)0.021 (3)0.007 (3)
C110.069 (4)0.085 (5)0.049 (4)0.023 (4)0.018 (3)0.024 (4)
C120.066 (4)0.041 (4)0.096 (5)0.001 (3)0.037 (4)0.007 (4)
C130.044 (4)0.066 (5)0.062 (4)0.015 (3)0.031 (3)0.006 (4)
C140.046 (3)0.055 (4)0.043 (3)0.011 (3)0.017 (3)0.013 (3)
C150.043 (3)0.044 (4)0.039 (3)0.003 (3)0.016 (3)0.004 (3)
C160.032 (3)0.038 (4)0.057 (4)0.003 (3)0.014 (3)0.001 (3)
C170.039 (3)0.044 (4)0.043 (3)0.008 (3)0.026 (3)0.010 (3)
C180.046 (4)0.042 (4)0.044 (3)0.007 (3)0.020 (3)0.002 (3)
C190.045 (4)0.087 (5)0.041 (3)0.015 (4)0.018 (3)0.011 (4)
C200.106 (6)0.099 (7)0.069 (5)0.003 (6)0.040 (4)0.029 (5)
C210.092 (6)0.125 (7)0.064 (4)0.013 (6)0.021 (4)0.013 (5)
C220.041 (3)0.049 (4)0.051 (4)0.002 (3)0.017 (3)0.006 (3)
C230.051 (4)0.050 (4)0.052 (4)0.006 (3)0.016 (3)0.005 (3)
C240.061 (4)0.075 (5)0.056 (4)0.010 (4)0.025 (3)0.007 (4)
C250.092 (5)0.097 (7)0.049 (4)0.015 (5)0.037 (4)0.003 (4)
C260.120 (7)0.071 (6)0.080 (5)0.006 (5)0.053 (5)0.022 (5)
C270.091 (5)0.055 (5)0.059 (4)0.013 (4)0.045 (4)0.006 (4)
C280.040 (3)0.042 (4)0.049 (3)0.010 (3)0.025 (3)0.002 (3)
C290.048 (4)0.063 (5)0.063 (4)0.013 (4)0.010 (3)0.003 (4)
C300.058 (4)0.058 (5)0.060 (4)0.015 (4)0.007 (3)0.008 (4)
C310.058 (4)0.061 (5)0.064 (5)0.013 (4)0.007 (4)0.005 (4)
C320.079 (5)0.049 (5)0.089 (5)0.015 (4)0.011 (5)0.015 (4)
C330.052 (4)0.057 (5)0.074 (5)0.001 (4)0.001 (4)0.015 (4)
C340.046 (4)0.049 (5)0.052 (4)0.008 (3)0.023 (3)0.010 (3)
C350.047 (4)0.055 (5)0.038 (3)0.009 (3)0.016 (3)0.000 (3)
C360.063 (4)0.063 (5)0.071 (4)0.003 (4)0.026 (4)0.023 (4)
C370.075 (5)0.083 (6)0.105 (6)0.025 (5)0.050 (5)0.021 (5)
C380.088 (6)0.106 (8)0.109 (7)0.008 (6)0.070 (5)0.021 (6)
C390.086 (6)0.108 (7)0.132 (7)0.007 (5)0.078 (5)0.009 (6)
C400.080 (4)0.053 (4)0.077 (4)0.011 (4)0.051 (4)0.003 (4)
F20.190 (5)0.147 (5)0.079 (3)0.012 (4)0.087 (3)0.003 (3)
O60.061 (3)0.066 (3)0.081 (3)0.008 (3)0.033 (2)0.004 (3)
O70.059 (3)0.048 (3)0.110 (4)0.002 (3)0.018 (3)0.022 (3)
O80.050 (2)0.052 (3)0.063 (3)0.014 (2)0.023 (2)0.004 (2)
O90.046 (2)0.051 (3)0.075 (3)0.010 (2)0.022 (2)0.008 (2)
O100.105 (4)0.044 (3)0.157 (5)0.011 (3)0.093 (4)0.024 (3)
N30.043 (3)0.051 (3)0.037 (3)0.011 (3)0.016 (2)0.007 (2)
N40.051 (3)0.046 (3)0.061 (3)0.006 (3)0.034 (3)0.008 (3)
C410.079 (6)0.078 (6)0.231 (10)0.012 (5)0.101 (7)0.005 (7)
C420.120 (7)0.043 (5)0.087 (5)0.016 (5)0.040 (5)0.009 (4)
C430.159 (9)0.104 (7)0.086 (6)0.024 (7)0.029 (6)0.043 (6)
C440.077 (5)0.047 (5)0.113 (6)0.013 (4)0.049 (5)0.005 (5)
C450.052 (4)0.042 (4)0.081 (5)0.006 (4)0.035 (4)0.007 (4)
C460.058 (4)0.067 (5)0.080 (4)0.021 (4)0.043 (4)0.009 (4)
C470.046 (3)0.047 (4)0.058 (4)0.001 (3)0.021 (3)0.004 (3)
C480.041 (3)0.052 (4)0.076 (4)0.006 (3)0.025 (3)0.006 (3)
C490.053 (4)0.051 (4)0.062 (4)0.010 (3)0.026 (3)0.008 (3)
C500.054 (4)0.062 (5)0.060 (4)0.011 (4)0.028 (3)0.014 (4)
C510.101 (6)0.057 (5)0.122 (6)0.007 (4)0.065 (5)0.008 (5)
C520.063 (4)0.128 (7)0.079 (5)0.033 (5)0.030 (4)0.044 (5)
C530.046 (4)0.050 (5)0.106 (5)0.007 (4)0.028 (4)0.022 (4)
C540.050 (4)0.048 (4)0.049 (3)0.015 (3)0.023 (3)0.007 (3)
C550.039 (3)0.042 (4)0.058 (4)0.003 (3)0.027 (3)0.005 (3)
C560.039 (3)0.037 (4)0.056 (4)0.001 (3)0.019 (3)0.006 (3)
C570.049 (4)0.042 (4)0.049 (4)0.001 (3)0.020 (3)0.001 (3)
C580.039 (3)0.050 (4)0.044 (3)0.003 (3)0.022 (3)0.001 (3)
C590.051 (4)0.070 (5)0.047 (4)0.011 (4)0.023 (3)0.004 (4)
C600.120 (7)0.102 (7)0.077 (5)0.011 (6)0.041 (5)0.040 (5)
C610.081 (5)0.111 (7)0.047 (4)0.017 (5)0.018 (3)0.016 (4)
C620.042 (3)0.048 (4)0.046 (3)0.013 (3)0.020 (3)0.002 (3)
C630.034 (3)0.057 (4)0.059 (4)0.007 (3)0.024 (3)0.005 (3)
C640.067 (4)0.066 (5)0.048 (4)0.020 (4)0.013 (3)0.010 (4)
C650.098 (6)0.097 (7)0.044 (4)0.001 (5)0.034 (4)0.001 (5)
C660.112 (6)0.082 (6)0.056 (5)0.004 (5)0.039 (4)0.015 (4)
C670.070 (5)0.058 (5)0.060 (4)0.003 (4)0.017 (4)0.003 (4)
C680.051 (4)0.049 (4)0.038 (3)0.009 (3)0.013 (3)0.003 (3)
C690.069 (5)0.033 (4)0.067 (4)0.007 (3)0.012 (4)0.006 (3)
C700.063 (5)0.067 (6)0.075 (5)0.008 (4)0.002 (4)0.020 (4)
C710.056 (4)0.071 (6)0.070 (5)0.020 (4)0.004 (4)0.006 (4)
C720.069 (5)0.057 (5)0.105 (6)0.017 (4)0.018 (5)0.015 (5)
C730.077 (5)0.042 (5)0.082 (5)0.014 (4)0.009 (4)0.001 (4)
C740.048 (4)0.045 (4)0.056 (4)0.010 (4)0.021 (3)0.005 (3)
C750.044 (4)0.077 (6)0.062 (4)0.003 (4)0.029 (3)0.008 (4)
C760.076 (5)0.065 (5)0.119 (6)0.019 (4)0.066 (5)0.003 (5)
C770.157 (10)0.092 (8)0.182 (10)0.025 (7)0.111 (8)0.004 (7)
C780.117 (8)0.156 (12)0.150 (10)0.020 (8)0.093 (7)0.022 (9)
C790.086 (6)0.133 (8)0.103 (6)0.019 (6)0.066 (5)0.007 (6)
C800.067 (4)0.076 (5)0.069 (4)0.011 (4)0.038 (4)0.016 (4)
Geometric parameters (Å, º) top
O1—C51.323 (8)F2—C651.359 (7)
O1—C41.496 (7)O6—C451.339 (7)
O2—C51.205 (7)O6—C441.472 (8)
O3—C101.414 (7)O7—C451.204 (7)
O3—C71.448 (6)O8—C471.425 (6)
O4—C101.414 (7)O8—C501.438 (7)
O4—C91.443 (6)O9—C501.436 (7)
O5—C341.241 (7)O9—C491.439 (6)
F1—C251.373 (7)O10—C741.205 (7)
N1—C181.383 (7)N3—C581.391 (7)
N1—C151.385 (6)N3—C551.406 (6)
N1—C141.486 (7)N3—C541.468 (6)
N2—C341.367 (7)N4—C741.330 (7)
N2—C351.420 (7)N4—C751.408 (7)
N2—H2A0.8600N4—H4A0.8600
C1—C41.477 (9)C41—C441.521 (9)
C1—H1A0.9600C41—H41A0.9600
C1—H1B0.9600C41—H41B0.9600
C1—H1C0.9600C41—H41C0.9600
C2—C41.518 (9)C42—C441.500 (9)
C2—H2B0.9600C42—H42A0.9600
C2—H2C0.9600C42—H42B0.9600
C2—H2D0.9600C42—H42C0.9600
C3—C41.496 (9)C43—C441.535 (9)
C3—H3A0.9600C43—H43A0.9600
C3—H3B0.9600C43—H43B0.9600
C3—H3C0.9600C43—H43C0.9600
C5—C61.497 (8)C45—C461.498 (8)
C6—C71.538 (7)C46—C471.504 (7)
C6—H6A0.9700C46—H46A0.9700
C6—H6B0.9700C46—H46B0.9700
C7—C81.518 (7)C47—C481.501 (6)
C7—H7A0.9800C47—H47A0.9800
C8—C91.522 (7)C48—C491.521 (7)
C8—H8A0.9700C48—H48A0.9700
C8—H8B0.9700C48—H48B0.9700
C9—C131.511 (7)C49—C531.512 (7)
C9—H9A0.9800C49—H49A0.9800
C10—C121.518 (8)C50—C521.501 (8)
C10—C111.531 (7)C50—C511.510 (9)
C11—H11A0.9600C51—H51A0.9600
C11—H11B0.9600C51—H51B0.9600
C11—H11C0.9600C51—H51C0.9600
C12—H12A0.9600C52—H52A0.9600
C12—H12B0.9600C52—H52B0.9600
C12—H12C0.9600C52—H52C0.9600
C13—C141.507 (8)C53—C541.498 (8)
C13—H13A0.9700C53—H53A0.9700
C13—H13B0.9700C53—H53B0.9700
C14—H14A0.9700C54—H54A0.9700
C14—H14B0.9700C54—H54B0.9700
C15—C161.375 (7)C55—C561.386 (7)
C15—C221.477 (7)C55—C621.456 (7)
C16—C171.410 (7)C56—C571.433 (7)
C16—C281.473 (7)C56—C681.481 (7)
C17—C181.370 (7)C57—C581.360 (7)
C17—C341.487 (8)C57—C741.525 (8)
C18—C191.500 (7)C58—C591.491 (7)
C19—C201.514 (9)C59—C611.510 (8)
C19—C211.544 (9)C59—C601.552 (9)
C19—H19A0.9800C59—H59A0.9800
C20—H20A0.9600C60—H60A0.9600
C20—H20B0.9600C60—H60B0.9600
C20—H20C0.9600C60—H60C0.9600
C21—H21A0.9600C61—H61A0.9600
C21—H21B0.9600C61—H61B0.9600
C21—H21C0.9600C61—H61C0.9600
C22—C271.392 (8)C62—C671.393 (8)
C22—C231.393 (8)C62—C631.404 (8)
C23—C241.367 (7)C63—C641.361 (7)
C23—H23A0.9300C63—H63A0.9300
C24—C251.350 (9)C64—C651.363 (9)
C24—H24A0.9300C64—H64A0.9300
C25—C261.350 (10)C65—C661.396 (10)
C26—C271.382 (8)C66—C671.377 (9)
C26—H26A0.9300C66—H66A0.9300
C27—H27A0.9300C67—H67A0.9300
C28—C331.367 (8)C68—C691.378 (8)
C28—C291.379 (8)C68—C731.401 (8)
C29—C301.384 (7)C69—C701.375 (8)
C29—H29A0.9300C69—H69A0.9300
C30—C311.369 (9)C70—C711.384 (9)
C30—H30A0.9300C70—H70A0.9300
C31—C321.369 (8)C71—C721.386 (8)
C31—H31A0.9300C71—H71A0.9300
C32—C331.379 (8)C72—C731.378 (8)
C32—H32A0.9300C72—H72A0.9300
C33—H33A0.9300C73—H73A0.9300
C35—C401.371 (8)C75—C761.363 (9)
C35—C361.372 (8)C75—C801.411 (8)
C36—C371.383 (8)C76—C771.407 (10)
C36—H36A0.9300C76—H76A0.9300
C37—C381.371 (10)C77—C781.368 (13)
C37—H37A0.9300C77—H77A0.9300
C38—C391.378 (10)C78—C791.354 (13)
C38—H38A0.9300C78—H78A0.9300
C39—C401.405 (8)C79—C801.356 (9)
C39—H39A0.9300C79—H79A0.9300
C40—H40A0.9300C80—H80A0.9300
C5—O1—C4121.7 (5)C45—O6—C44121.6 (5)
C10—O3—C7114.7 (4)C47—O8—C50114.8 (5)
C10—O4—C9114.9 (4)C50—O9—C49114.6 (5)
C18—N1—C15109.4 (5)C58—N3—C55109.4 (4)
C18—N1—C14125.8 (4)C58—N3—C54125.2 (4)
C15—N1—C14124.3 (4)C55—N3—C54124.9 (4)
C34—N2—C35129.1 (5)C74—N4—C75125.8 (6)
C34—N2—H2A115.5C74—N4—H4A117.1
C35—N2—H2A115.5C75—N4—H4A117.1
C4—C1—H1A109.5C44—C41—H41A109.5
C4—C1—H1B109.5C44—C41—H41B109.5
H1A—C1—H1B109.5H41A—C41—H41B109.5
C4—C1—H1C109.5C44—C41—H41C109.5
H1A—C1—H1C109.5H41A—C41—H41C109.5
H1B—C1—H1C109.5H41B—C41—H41C109.5
C4—C2—H2B109.5C44—C42—H42A109.5
C4—C2—H2C109.5C44—C42—H42B109.5
H2B—C2—H2C109.5H42A—C42—H42B109.5
C4—C2—H2D109.5C44—C42—H42C109.5
H2B—C2—H2D109.5H42A—C42—H42C109.5
H2C—C2—H2D109.5H42B—C42—H42C109.5
C4—C3—H3A109.5C44—C43—H43A109.5
C4—C3—H3B109.5C44—C43—H43B109.5
H3A—C3—H3B109.5H43A—C43—H43B109.5
C4—C3—H3C109.5C44—C43—H43C109.5
H3A—C3—H3C109.5H43A—C43—H43C109.5
H3B—C3—H3C109.5H43B—C43—H43C109.5
C1—C4—O1109.8 (6)O6—C44—C42110.4 (6)
C1—C4—C3114.4 (7)O6—C44—C41109.1 (6)
O1—C4—C3109.2 (6)C42—C44—C41114.5 (7)
C1—C4—C2109.8 (6)O6—C44—C43101.5 (6)
O1—C4—C2101.7 (5)C42—C44—C43110.0 (7)
C3—C4—C2111.0 (6)C41—C44—C43110.7 (7)
O2—C5—O1124.5 (6)O7—C45—O6124.5 (6)
O2—C5—C6124.2 (7)O7—C45—C46123.7 (7)
O1—C5—C6111.3 (6)O6—C45—C46111.7 (6)
C5—C6—C7109.3 (5)C45—C46—C47110.4 (5)
C5—C6—H6A109.8C45—C46—H46A109.6
C7—C6—H6A109.8C47—C46—H46A109.6
C5—C6—H6B109.8C45—C46—H46B109.6
C7—C6—H6B109.8C47—C46—H46B109.6
H6A—C6—H6B108.3H46A—C46—H46B108.1
O3—C7—C8109.1 (4)O8—C47—C48109.4 (4)
O3—C7—C6106.1 (4)O8—C47—C46105.7 (5)
C8—C7—C6112.8 (5)C48—C47—C46113.1 (5)
O3—C7—H7A109.6O8—C47—H47A109.5
C8—C7—H7A109.6C48—C47—H47A109.5
C6—C7—H7A109.6C46—C47—H47A109.5
C7—C8—C9109.3 (5)C47—C48—C49111.6 (5)
C7—C8—H8A109.8C47—C48—H48A109.3
C9—C8—H8A109.8C49—C48—H48A109.3
C7—C8—H8B109.8C47—C48—H48B109.3
C9—C8—H8B109.8C49—C48—H48B109.3
H8A—C8—H8B108.3H48A—C48—H48B108.0
O4—C9—C13107.2 (4)O9—C49—C53106.4 (5)
O4—C9—C8109.1 (4)O9—C49—C48109.4 (5)
C13—C9—C8111.4 (5)C53—C49—C48110.5 (5)
O4—C9—H9A109.7O9—C49—H49A110.2
C13—C9—H9A109.7C53—C49—H49A110.2
C8—C9—H9A109.7C48—C49—H49A110.2
O3—C10—O4110.9 (5)O9—C50—O8108.4 (5)
O3—C10—C12110.7 (5)O9—C50—C52111.7 (5)
O4—C10—C12113.4 (5)O8—C50—C52112.3 (5)
O3—C10—C11104.3 (5)O9—C50—C51106.7 (6)
O4—C10—C11106.7 (5)O8—C50—C51107.1 (6)
C12—C10—C11110.5 (6)C52—C50—C51110.5 (6)
C10—C11—H11A109.5C50—C51—H51A109.5
C10—C11—H11B109.5C50—C51—H51B109.5
H11A—C11—H11B109.5H51A—C51—H51B109.5
C10—C11—H11C109.5C50—C51—H51C109.5
H11A—C11—H11C109.5H51A—C51—H51C109.5
H11B—C11—H11C109.5H51B—C51—H51C109.5
C10—C12—H12A109.5C50—C52—H52A109.5
C10—C12—H12B109.5C50—C52—H52B109.5
H12A—C12—H12B109.5H52A—C52—H52B109.5
C10—C12—H12C109.5C50—C52—H52C109.5
H12A—C12—H12C109.5H52A—C52—H52C109.5
H12B—C12—H12C109.5H52B—C52—H52C109.5
C14—C13—C9113.3 (6)C54—C53—C49115.6 (5)
C14—C13—H13A108.9C54—C53—H53A108.4
C9—C13—H13A108.9C49—C53—H53A108.4
C14—C13—H13B108.9C54—C53—H53B108.4
C9—C13—H13B108.9C49—C53—H53B108.4
H13A—C13—H13B107.7H53A—C53—H53B107.4
N1—C14—C13113.2 (5)N3—C54—C53113.5 (5)
N1—C14—H14A108.9N3—C54—H54A108.9
C13—C14—H14A108.9C53—C54—H54A108.9
N1—C14—H14B108.9N3—C54—H54B108.9
C13—C14—H14B108.9C53—C54—H54B108.9
H14A—C14—H14B107.8H54A—C54—H54B107.7
C16—C15—N1107.6 (5)C56—C55—N3106.7 (5)
C16—C15—C22129.4 (5)C56—C55—C62129.3 (5)
N1—C15—C22122.5 (5)N3—C55—C62123.9 (5)
C15—C16—C17107.3 (5)C55—C56—C57107.6 (5)
C15—C16—C28125.2 (5)C55—C56—C68125.8 (5)
C17—C16—C28127.3 (5)C57—C56—C68126.4 (5)
C18—C17—C16108.8 (5)C58—C57—C56108.5 (5)
C18—C17—C34127.8 (5)C58—C57—C74127.6 (5)
C16—C17—C34123.4 (5)C56—C57—C74123.9 (5)
C17—C18—N1107.0 (5)C57—C58—N3107.9 (5)
C17—C18—C19132.0 (5)C57—C58—C59130.5 (5)
N1—C18—C19120.6 (5)N3—C58—C59121.5 (5)
C18—C19—C20111.7 (5)C58—C59—C61114.4 (6)
C18—C19—C21111.8 (5)C58—C59—C60110.3 (5)
C20—C19—C21109.9 (5)C61—C59—C60110.7 (5)
C18—C19—H19A107.8C58—C59—H59A107.0
C20—C19—H19A107.8C61—C59—H59A107.0
C21—C19—H19A107.8C60—C59—H59A107.0
C19—C20—H20A109.5C59—C60—H60A109.5
C19—C20—H20B109.5C59—C60—H60B109.5
H20A—C20—H20B109.5H60A—C60—H60B109.5
C19—C20—H20C109.5C59—C60—H60C109.5
H20A—C20—H20C109.5H60A—C60—H60C109.5
H20B—C20—H20C109.5H60B—C60—H60C109.5
C19—C21—H21A109.5C59—C61—H61A109.5
C19—C21—H21B109.5C59—C61—H61B109.5
H21A—C21—H21B109.5H61A—C61—H61B109.5
C19—C21—H21C109.5C59—C61—H61C109.5
H21A—C21—H21C109.5H61A—C61—H61C109.5
H21B—C21—H21C109.5H61B—C61—H61C109.5
C27—C22—C23117.5 (5)C67—C62—C63117.5 (5)
C27—C22—C15119.0 (6)C67—C62—C55119.1 (6)
C23—C22—C15123.4 (6)C63—C62—C55123.4 (6)
C24—C23—C22121.9 (6)C64—C63—C62122.5 (6)
C24—C23—H23A119.1C64—C63—H63A118.7
C22—C23—H23A119.1C62—C63—H63A118.7
C25—C24—C23118.4 (7)C63—C64—C65117.9 (7)
C25—C24—H24A120.8C63—C64—H64A121.1
C23—C24—H24A120.8C65—C64—H64A121.1
C26—C25—C24122.3 (6)F2—C65—C64119.6 (8)
C26—C25—F1118.9 (8)F2—C65—C66117.7 (7)
C24—C25—F1118.7 (8)C64—C65—C66122.7 (7)
C25—C26—C27119.8 (7)C67—C66—C65118.1 (7)
C25—C26—H26A120.1C67—C66—H66A120.9
C27—C26—H26A120.1C65—C66—H66A120.9
C26—C27—C22119.8 (7)C66—C67—C62121.1 (7)
C26—C27—H27A120.1C66—C67—H67A119.4
C22—C27—H27A120.1C62—C67—H67A119.4
C33—C28—C29116.4 (6)C69—C68—C73118.5 (6)
C33—C28—C16122.9 (6)C69—C68—C56119.8 (6)
C29—C28—C16120.6 (6)C73—C68—C56121.6 (6)
C28—C29—C30122.3 (7)C70—C69—C68121.1 (6)
C28—C29—H29A118.8C70—C69—H69A119.5
C30—C29—H29A118.8C68—C69—H69A119.5
C31—C30—C29119.9 (7)C69—C70—C71120.7 (7)
C31—C30—H30A120.1C69—C70—H70A119.6
C29—C30—H30A120.1C71—C70—H70A119.6
C30—C31—C32118.6 (7)C70—C71—C72118.5 (7)
C30—C31—H31A120.7C70—C71—H71A120.8
C32—C31—H31A120.7C72—C71—H71A120.8
C31—C32—C33120.6 (7)C73—C72—C71121.2 (7)
C31—C32—H32A119.7C73—C72—H72A119.4
C33—C32—H32A119.7C71—C72—H72A119.4
C28—C33—C32122.1 (6)C72—C73—C68119.9 (7)
C28—C33—H33A119.0C72—C73—H73A120.0
C32—C33—H33A119.0C68—C73—H73A120.0
O5—C34—N2121.7 (6)O10—C74—N4124.5 (6)
O5—C34—C17122.9 (6)O10—C74—C57121.4 (6)
N2—C34—C17115.4 (5)N4—C74—C57114.1 (6)
C40—C35—C36120.0 (6)C76—C75—N4123.2 (7)
C40—C35—N2116.4 (6)C76—C75—C80119.7 (6)
C36—C35—N2123.5 (6)N4—C75—C80117.1 (6)
C35—C36—C37120.3 (7)C75—C76—C77119.4 (8)
C35—C36—H36A119.8C75—C76—H76A120.3
C37—C36—H36A119.8C77—C76—H76A120.3
C38—C37—C36121.2 (8)C78—C77—C76119.1 (9)
C38—C37—H37A119.4C78—C77—H77A120.5
C36—C37—H37A119.4C76—C77—H77A120.5
C37—C38—C39118.0 (7)C79—C78—C77121.7 (10)
C37—C38—H38A121.0C79—C78—H78A119.2
C39—C38—H38A121.0C77—C78—H78A119.2
C38—C39—C40121.6 (7)C78—C79—C80120.1 (9)
C38—C39—H39A119.2C78—C79—H79A119.9
C40—C39—H39A119.2C80—C79—H79A119.9
C35—C40—C39118.8 (7)C79—C80—C75120.0 (8)
C35—C40—H40A120.6C79—C80—H80A120.0
C39—C40—H40A120.6C75—C80—H80A120.0
C5—O1—C4—C162.9 (8)C45—O6—C44—C4259.2 (8)
C5—O1—C4—C363.3 (8)C45—O6—C44—C4167.4 (8)
C5—O1—C4—C2179.3 (5)C45—O6—C44—C43175.7 (6)
C4—O1—C5—O23.0 (10)C44—O6—C45—O73.1 (10)
C4—O1—C5—C6177.5 (5)C44—O6—C45—C46172.4 (6)
O2—C5—C6—C7114.3 (7)O7—C45—C46—C4769.0 (8)
O1—C5—C6—C766.2 (6)O6—C45—C46—C47106.5 (6)
C10—O3—C7—C856.0 (6)C50—O8—C47—C4856.8 (6)
C10—O3—C7—C6177.8 (5)C50—O8—C47—C46178.8 (4)
C5—C6—C7—O346.2 (6)C45—C46—C47—O852.7 (7)
C5—C6—C7—C8165.5 (5)C45—C46—C47—C48172.4 (5)
O3—C7—C8—C954.3 (6)O8—C47—C48—C4951.4 (6)
C6—C7—C8—C9171.9 (5)C46—C47—C48—C49168.9 (5)
C10—O4—C9—C13176.5 (5)C50—O9—C49—C53174.3 (5)
C10—O4—C9—C855.7 (6)C50—O9—C49—C4854.9 (6)
C7—C8—C9—O454.2 (6)C47—C48—C49—O950.6 (6)
C7—C8—C9—C13172.4 (5)C47—C48—C49—C53167.4 (5)
C7—O3—C10—O455.2 (6)C49—O9—C50—O857.7 (6)
C7—O3—C10—C1271.5 (6)C49—O9—C50—C5266.6 (7)
C7—O3—C10—C11169.7 (5)C49—O9—C50—C51172.7 (5)
C9—O4—C10—O355.2 (6)C47—O8—C50—O958.7 (6)
C9—O4—C10—C1270.0 (6)C47—O8—C50—C5265.1 (7)
C9—O4—C10—C11168.2 (5)C47—O8—C50—C51173.5 (5)
O4—C9—C13—C1469.7 (6)O9—C49—C53—C5447.4 (7)
C8—C9—C13—C14171.0 (5)C48—C49—C53—C54166.1 (6)
C18—N1—C14—C13101.0 (6)C58—N3—C54—C53112.1 (6)
C15—N1—C14—C1370.0 (7)C55—N3—C54—C5358.3 (8)
C9—C13—C14—N1165.0 (4)C49—C53—C54—N3161.4 (5)
C18—N1—C15—C161.9 (7)C58—N3—C55—C560.1 (6)
C14—N1—C15—C16174.1 (5)C54—N3—C55—C56171.8 (5)
C18—N1—C15—C22170.2 (6)C58—N3—C55—C62177.3 (6)
C14—N1—C15—C222.0 (9)C54—N3—C55—C625.6 (9)
N1—C15—C16—C171.3 (7)N3—C55—C56—C570.6 (6)
C22—C15—C16—C17170.1 (6)C62—C55—C56—C57176.6 (6)
N1—C15—C16—C28173.4 (5)N3—C55—C56—C68173.8 (6)
C22—C15—C16—C2815.2 (10)C62—C55—C56—C689.0 (10)
C15—C16—C17—C180.3 (7)C55—C56—C57—C580.9 (7)
C28—C16—C17—C18174.3 (6)C68—C56—C57—C58173.5 (6)
C15—C16—C17—C34178.1 (5)C55—C56—C57—C74179.0 (6)
C28—C16—C17—C347.3 (10)C68—C56—C57—C746.6 (10)
C16—C17—C18—N10.9 (7)C56—C57—C58—N30.8 (7)
C34—C17—C18—N1179.2 (6)C74—C57—C58—N3179.1 (6)
C16—C17—C18—C19173.1 (6)C56—C57—C58—C59175.1 (6)
C34—C17—C18—C198.7 (11)C74—C57—C58—C595.0 (11)
C15—N1—C18—C171.7 (7)C55—N3—C58—C570.4 (7)
C14—N1—C18—C17173.8 (5)C54—N3—C58—C57171.3 (5)
C15—N1—C18—C19175.0 (5)C55—N3—C58—C59175.9 (5)
C14—N1—C18—C1912.9 (9)C54—N3—C58—C5912.4 (9)
C17—C18—C19—C2094.3 (8)C57—C58—C59—C6127.6 (10)
N1—C18—C19—C2077.0 (7)N3—C58—C59—C61157.0 (6)
C17—C18—C19—C2129.3 (10)C57—C58—C59—C6098.0 (8)
N1—C18—C19—C21159.3 (6)N3—C58—C59—C6077.5 (7)
C16—C15—C22—C2745.3 (9)C56—C55—C62—C6746.7 (9)
N1—C15—C22—C27124.9 (6)N3—C55—C62—C67130.1 (6)
C16—C15—C22—C23133.7 (7)C56—C55—C62—C63133.8 (7)
N1—C15—C22—C2356.0 (8)N3—C55—C62—C6349.4 (8)
C27—C22—C23—C245.0 (9)C67—C62—C63—C644.0 (9)
C15—C22—C23—C24175.9 (5)C55—C62—C63—C64175.6 (5)
C22—C23—C24—C253.2 (9)C62—C63—C64—C652.0 (9)
C23—C24—C25—C260.3 (11)C63—C64—C65—F2180.0 (6)
C23—C24—C25—F1180.0 (6)C63—C64—C65—C661.0 (11)
C24—C25—C26—C271.7 (13)F2—C65—C66—C67179.1 (6)
F1—C25—C26—C27178.5 (6)C64—C65—C66—C671.9 (13)
C25—C26—C27—C220.3 (12)C65—C66—C67—C620.2 (11)
C23—C22—C27—C263.5 (9)C63—C62—C67—C663.0 (9)
C15—C22—C27—C26177.4 (6)C55—C62—C67—C66176.6 (6)
C15—C16—C28—C33132.7 (7)C55—C56—C68—C6955.3 (9)
C17—C16—C28—C3353.7 (9)C57—C56—C68—C69118.1 (7)
C15—C16—C28—C2949.7 (9)C55—C56—C68—C73127.7 (7)
C17—C16—C28—C29123.9 (7)C57—C56—C68—C7358.9 (10)
C33—C28—C29—C302.3 (10)C73—C68—C69—C704.2 (10)
C16—C28—C29—C30180.0 (6)C56—C68—C69—C70178.7 (6)
C28—C29—C30—C311.2 (10)C68—C69—C70—C712.7 (11)
C29—C30—C31—C321.3 (11)C69—C70—C71—C720.4 (12)
C30—C31—C32—C332.5 (11)C70—C71—C72—C730.3 (12)
C29—C28—C33—C321.1 (11)C71—C72—C73—C681.2 (13)
C16—C28—C33—C32178.7 (6)C69—C68—C73—C723.4 (11)
C31—C32—C33—C281.3 (12)C56—C68—C73—C72179.5 (7)
C35—N2—C34—O50.4 (10)C75—N4—C74—O102.6 (10)
C35—N2—C34—C17179.9 (5)C75—N4—C74—C57179.2 (5)
C18—C17—C34—O589.5 (9)C58—C57—C74—O1097.0 (9)
C16—C17—C34—O588.5 (8)C56—C57—C74—O1082.9 (9)
C18—C17—C34—N290.2 (7)C58—C57—C74—N484.7 (8)
C16—C17—C34—N291.8 (7)C56—C57—C74—N495.4 (7)
C34—N2—C35—C40178.1 (5)C74—N4—C75—C7629.9 (10)
C34—N2—C35—C362.1 (9)C74—N4—C75—C80147.5 (6)
C40—C35—C36—C371.0 (10)N4—C75—C76—C77179.5 (7)
N2—C35—C36—C37179.3 (5)C80—C75—C76—C773.2 (11)
C35—C36—C37—C380.5 (11)C75—C76—C77—C782.6 (14)
C36—C37—C38—C391.3 (13)C76—C77—C78—C792.0 (17)
C37—C38—C39—C400.8 (13)C77—C78—C79—C802.1 (17)
C36—C35—C40—C391.5 (9)C78—C79—C80—C752.7 (12)
N2—C35—C40—C39178.8 (5)C76—C75—C80—C793.3 (10)
C38—C39—C40—C350.6 (12)N4—C75—C80—C79179.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.052.899 (7)168
N4—H4A···O7ii0.862.072.914 (7)168
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.052.899 (7)168
N4—H4A···O7ii0.862.072.914 (7)168
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

Acknowledgements

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

References

First citationAllen, 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
First citationEnraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationZhang, Z., Mei, G., Fang, Z., Meng, X. & Wu, J. (2012). Patent CN 102766136.

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