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

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ISSN: 2056-9890

Ethyl 5-[(1H-benzoimidazol-2-yl)amino­carbon­yl]-4-hydr­­oxy-2-methyl-6-oxo-1-propyl-1,6-di­hydro­pyridine-3-carboxyl­ate–ethanol–methanol (4/2/1)

aSTC "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine, and bNational University of Pharmacy, 4 Blyukhera ave., Kharkiv 61002, Ukraine
*Correspondence e-mail: sveta@xray.isc.kharkov.com

(Received 9 June 2009; accepted 8 July 2009; online 25 July 2009)

The asymmetric unit of the title compound, 4C20H22N4O5·2C2H6O·CH4O, contains two pyridine-3-carboxyl­ate mol­ecules, one ethanol mol­ecule and one methanol mol­ecule disordered about in a centre of symmetry. The pyridinone ring, the carbamide group and the bicyclic fragment in both independent mol­ecules are planar within 0.03 Å due to the formation of intra­molecular O—H⋯O and N—H⋯O hydrogen bonds. The formation of these latter inter­actions also causes the redistribution of the electron density within the hydroxy­pyridone fragment, with the result that some bonds are elongated compared with values in the literature and some others are shorter. In the crystal phase, the pyridine-3-carboxyl­ate mol­ecules form layers parallel to (010), which are inter­linked through hydrogen bonds mediated by the bridging solvate mol­ecules. A terminal ethyl group in one of the mol­ecules is disordered over two sites of equally occupancy.

Related literature

For general properties of N-acylic derivatives of 2-amino­benzoimidazole, see: Ukrainets et al. (1993[Ukrainets, I. V., Bezugly, P. A., Gorokhova, O. V., Treskach, V. I. & Turov, A. V. (1993). Khim. Geterotsikl. Soedin. pp. 105-108.], 2006[Ukrainets, I. V., Sidorenko, L. V., Gorokhova, O. V. & Shishkin, O. V. (2006). Khim. Geterotsikl. Soedin. pp. 217-223.]). For the geometrical properties of related compounds, see: Bürgi & Dunitz (1994[Bürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767-784. Weinheim: VCH.]); Low & Wilson (1983[Low, J. N. & Wilson, C. C. (1983). Acta Cryst. C39, 1688-1690.]).

[Scheme 1]

Experimental

Crystal data
  • 4C20H22N4O5·2C2H6O·CH4O

  • Mr = 1717.84

  • Triclinic, [P \overline 1]

  • a = 10.5527 (4) Å

  • b = 13.9720 (4) Å

  • c = 16.0242 (5) Å

  • α = 86.804 (3)°

  • β = 70.980 (3)°

  • γ = 78.652 (3)°

  • V = 2189.90 (12) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.40 × 0.30 × 0.10 mm

Data collection
  • Oxford Diffraction Xcalibur3 diffractometer

  • Absorption correction: none

  • 23866 measured reflections

  • 7499 independent reflections

  • 3785 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.170

  • S = 0.89

  • 7499 reflections

  • 596 parameters

  • 9 restraints

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1A—H1A⋯O3A 0.82 1.77 2.503 (2) 149
O1B—H1B⋯O3B 0.82 1.78 2.508 (2) 148
N2A—H2A⋯O2A 0.86 1.88 2.600 (3) 140
N2B—H2B⋯O2B 0.86 1.88 2.596 (3) 139
N3A—H3A⋯O2i 0.86 2.34 2.968 (3) 130
N3A—H3A⋯O3A 0.86 2.21 2.710 (3) 117
N3B—H3B⋯O1ii 0.86 2.46 3.106 (6) 132
N3B—H3B⋯O3B 0.86 2.18 2.691 (3) 118
O2—H2⋯N4A 0.82 2.27 2.926 (3) 138
O1—H1⋯N4B 0.82 2.35 3.050 (6) 144
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2005[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2005[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: XP (Bruker, 1998[Bruker (1998). XP. Bruker AXS Inc., Karlsruhe, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

N-acylic derivatives of 2-aminobenzoimidazole are considered as potential antithyroid drugs (Ukrainets et al., 1993), for what the structures of these compounds are of particular interest. In the present paper, we report the crystal structure of ethyl-5(1H- benzoimidazol-2-ylcarbamoyl)-4-hydroxy-2-methyl-6-oxo-1-propyl-1,6- dihydropyridine-3-carboxylate (I). The compound exists as a ethanol:methanol solvate in a 4:2:1 ratio. The asymmetric unit contains two molecules (A and B) of I, one ethanol molecule and one methanol molecule located in a centre of symmetry. The pyridinone ring, the carbamide group and the bicyclic fragment in molecules A and B lie in a plane within 0.03 Å due to the formation of many O—H···O, N—H···O intramolecular hydrogen bonds (Table 1, top eight entries). The formation of these hydrogen bonds causes also the redistribution of the electron density within the hydroxypyridone fragment. The O2—C5, O3—C6 and C3—C4 bonds (See Supplementary Material) are elongated as compared with reported value (mean values in the literature: 1.210 Å for the C=O and 1.326 Å for the C—C bond; Bürgi & Dunitz, 1994) and the O1—C3 and C4—C5 bonds are, instead, shorter (mean values in the literature: 1.362 Å and 1.455 Å). Some elongation of the C1—C2 bond and shortening of the C2—C3 bond can be caused, probably, by the strong conjugation between endocyclic double bonds which is typical for the pyridinone ring (Low & Wilson, 1983). The substituent at the C2 atom is turned relatively to the plane of the heterocycle (C1—C2—C17—O4 torsion angle: 47.2 (4) ° in A and 59.3 (4) ° in B). The ethyl group has sp-conformation relatively to the C17—O4 bond (C18—O5—C17—O4 torsion angle: 6.0 (5) Å (A) 7.3 (5) Å (B)). In molecule B the ethyl group is orthogonal to the C17—O5 bond (C17—O5—C18—C19 torsion angle: 84.0 (4) °) while in the molecule A this group is disordered over three positions due to the rotation around the O5—C18 bond with populations 0.50:0.25:0.25 and C17—O5—C18—C19 torsion angle: 175.0 (5) °, 139.3 (9) %A and 92 (1) °, respectively. In the crystal phase the molecules of I form layers parallel to (010). Neighbouring layers are interlinked through H-bonds mediated by the bridging solvate molecules (Table 1, last two entries).

Related literature top

For general properties of N-acylic derivatives of 2-aminobenzoimidazole, see: Ukrainets et al. (1993, 2006). For the geometrical properties of related compounds, see: Bürgi & Dunitz (1994); Low & Wilson (1983)

Experimental top

A mixture of diethyl 4-hydroxy-2-methyl-6-oxo-1-propyl-1,6-dihydro- pyridine-3,5-dicarboxylate (Ukrainets et al., 2006) (3.11 g, 10.0 mmol), 2-aminobenzimidazole (1.33 g, 10.0 mmol), and DMF (1 ml) was stirred an kept on a metal bath at 160%A C for 5 min. The mixture was cooled, ethanol (30 ml) was added, the mixture was thoroughly mixed and filtered. The amino-ester obtained was washed on the filter with ethanol and dried. Yield 3.58 g (83%). m.p. 154–156%A C.

Refinement top

Crystals were multiple and poorly diffracting: in the specimen used no reflections appeared above 2θ = 50°, for what this was taken as the integration limit. Besides, some reflections were rejected in the integration process due to overlap with minor components. Restrictions on bond lengths (Csp3—Csp3 1.54 (1) Å, Csp3—O 1.43 (1) Å) in the solvate molecules and the disordered fragment were applied during refinement. The occupation factor for the latter group were refined for a few cycles, rounded up and kept fixed for the rest of the process. Hydrogen atoms were located from electron density difference maps and further idealized, or were calculated geometrically for the disordered fragment and solvate molecules, and were refined in the riding motion approximation with Uiso constrained to be 1.5 times Ueq of the carrier atom for the methyl and hydroxyl groups and 1.2 times Ueq of the carrier atom for the other atoms.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular view of the title compound with atomic labelling. All atoms are shown with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms and minor components of disordered ethyl group in molecule A omitted for clarity.
[Figure 2] Fig. 2. The packing of the molecules in the crystal phase. Hydrogen bonds between molecules of (I) and bridging solvate molecules are shown by dashed lines.
Ethyl 5-[(1H-benzoimidazol-2-yl)aminocarbonyl]-4-hydroxy-2-methyl-6-oxo-1-propyl-1,6-dihydropyridine-3-carboxylate–ethanol–methanol (4/2/1) top
Crystal data top
4C20H22N4O5·2C2H6O·CH4OZ = 1
Mr = 1717.84F(000) = 910
Triclinic, P1Dx = 1.303 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5527 (4) ÅCell parameters from 6420 reflections
b = 13.9720 (4) Åθ = 2.7–32.1°
c = 16.0242 (5) ŵ = 0.10 mm1
α = 86.804 (3)°T = 293 K
β = 70.980 (3)°Plate, colourless
γ = 78.652 (3)°0.40 × 0.30 × 0.10 mm
V = 2189.90 (12) Å3
Data collection top
Oxford Diffraction Xcalibur3
diffractometer
3785 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.030
Graphite monochromatorθmax = 25.0°, θmin = 2.8°
Detector resolution: 16.1827 pixels mm-1h = 1212
ω scansk = 1616
23866 measured reflectionsl = 1919
7499 independent reflections
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 0.89 w = 1/[σ2(Fo2) + (0.1051P)2]
where P = (Fo2 + 2Fc2)/3
7499 reflections(Δ/σ)max = 0.001
596 parametersΔρmax = 0.44 e Å3
9 restraintsΔρmin = 0.35 e Å3
Crystal data top
4C20H22N4O5·2C2H6O·CH4Oγ = 78.652 (3)°
Mr = 1717.84V = 2189.90 (12) Å3
Triclinic, P1Z = 1
a = 10.5527 (4) ÅMo Kα radiation
b = 13.9720 (4) ŵ = 0.10 mm1
c = 16.0242 (5) ÅT = 293 K
α = 86.804 (3)°0.40 × 0.30 × 0.10 mm
β = 70.980 (3)°
Data collection top
Oxford Diffraction Xcalibur3
diffractometer
3785 reflections with I > 2σ(I)
23866 measured reflectionsRint = 0.030
7499 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0559 restraints
wR(F2) = 0.170H-atom parameters constrained
S = 0.89Δρmax = 0.44 e Å3
7499 reflectionsΔρmin = 0.35 e Å3
596 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*/UeqOcc. (<1)
O10.8136 (6)0.0281 (4)0.5379 (4)0.1256 (19)0.50
H10.74740.00310.57520.188*0.50
C10.9280 (7)0.0168 (6)0.5292 (5)0.104 (3)0.50
H131.00730.01840.48590.156*0.50
H120.91020.08340.51120.156*0.50
H110.94360.01480.58510.156*0.50
O20.7030 (3)0.5258 (2)0.04837 (18)0.1089 (9)
H20.73040.57750.05420.163*
C20.6397 (5)0.5185 (4)0.1135 (3)0.1353 (17)
H220.54140.53380.08610.162*
H210.66370.45170.13490.162*
C30.6811 (5)0.5866 (4)0.1923 (3)0.1401 (19)
H330.62540.58560.22910.210*
H320.77530.56480.22600.210*
H310.66830.65190.17120.210*
O1A0.93576 (19)0.61024 (15)0.32098 (12)0.0634 (5)
H1A0.99050.60730.27090.095*
O2A0.61620 (18)0.64723 (13)0.16678 (12)0.0577 (5)
O3A1.0200 (2)0.62015 (14)0.15611 (12)0.0619 (5)
O4A0.6881 (3)0.55814 (18)0.53908 (16)0.1086 (10)
O5A0.8100 (2)0.67441 (14)0.49024 (12)0.0663 (6)
N1A0.5464 (2)0.63870 (14)0.31662 (13)0.0470 (5)
N2A0.8745 (2)0.62809 (14)0.07776 (13)0.0491 (5)
H2A0.79050.63340.08100.059*
N3A1.1051 (2)0.61149 (14)0.02264 (14)0.0507 (5)
H3A1.14760.60710.01540.061*
N4A0.9310 (2)0.62716 (15)0.07671 (14)0.0518 (6)
C1A0.5712 (3)0.63431 (17)0.39529 (16)0.0464 (6)
C2A0.7019 (3)0.62597 (17)0.39704 (16)0.0478 (6)
C3A0.8109 (3)0.62374 (17)0.31688 (16)0.0454 (6)
C4A0.7849 (3)0.63165 (16)0.23636 (15)0.0439 (6)
C5A0.6497 (3)0.64032 (16)0.23452 (17)0.0432 (6)
C6A0.9007 (3)0.62683 (17)0.15455 (17)0.0469 (6)
C7A0.9693 (3)0.62164 (16)0.00579 (16)0.0452 (6)
C8A1.1622 (3)0.60966 (17)0.11410 (17)0.0493 (7)
C9A1.2972 (3)0.60238 (19)0.16880 (19)0.0610 (8)
H9A1.36950.59560.14650.073*
C10A1.3164 (3)0.60597 (19)0.2586 (2)0.0650 (8)
H10A1.40450.60190.29790.078*
C11A1.2089 (3)0.61542 (19)0.29163 (19)0.0622 (8)
H11A1.22670.61750.35240.075*
C12A1.0771 (3)0.62182 (19)0.23733 (18)0.0596 (7)
H12A1.00570.62760.26040.072*
C13A1.0530 (3)0.61940 (17)0.14619 (17)0.0480 (6)
C14A0.4088 (3)0.6390 (2)0.31050 (19)0.0567 (7)
H14B0.35590.60910.36300.068*
H14A0.41850.59960.26000.068*
C15A0.3321 (3)0.7395 (2)0.3014 (2)0.0699 (8)
H15B0.31440.77730.35430.084*
H15A0.38800.77190.25190.084*
C16A0.1993 (3)0.7370 (3)0.2871 (3)0.0963 (11)
H16C0.14300.70580.33630.144*
H16B0.21640.70100.23390.144*
H16A0.15330.80240.28190.144*
C17A0.7317 (3)0.6147 (2)0.48234 (18)0.0608 (8)
C18A0.8539 (4)0.6630 (3)0.5673 (2)0.0959 (12)
H18A0.89920.59620.57110.115*0.50
H18B0.77590.67850.62030.115*0.50
H18E0.84630.59900.59280.115*0.25
H18F0.79930.71230.61150.115*0.25
H18G0.78820.63620.61560.115*0.25
H18H0.86280.72560.58580.115*0.25
C19A0.9530 (10)0.7334 (8)0.5579 (7)0.107 (4)0.50
H19A0.98410.72750.60830.161*0.50
H19B0.90700.79920.55420.161*0.50
H19C1.02980.71730.50530.161*0.50
C19C1.0040 (8)0.6754 (17)0.5334 (12)0.098 (7)0.25
H19G1.00800.74260.51900.146*0.25
H19H1.05210.63560.48160.146*0.25
H19I1.04540.65580.57830.146*0.25
C19D0.9929 (14)0.5928 (15)0.5406 (10)0.129 (7)0.25
H19J0.97960.52760.55750.194*0.25
H19K1.05020.61210.56990.194*0.25
H19L1.03570.59500.47790.194*0.25
C20A0.4504 (3)0.6403 (2)0.47764 (18)0.0637 (8)
H20C0.38040.69400.47340.095*
H20B0.47750.65000.52770.095*
H20A0.41580.58070.48450.095*
O1B0.5138 (2)0.15276 (16)0.20358 (12)0.0661 (5)
H1B0.45900.15670.25370.099*
O2B0.83685 (19)0.12699 (14)0.35437 (12)0.0621 (5)
O3B0.4315 (2)0.14907 (14)0.36909 (11)0.0626 (5)
O4B0.7561 (3)0.0800 (2)0.01009 (16)0.1132 (10)
O5B0.6275 (2)0.22567 (15)0.03465 (13)0.0774 (6)
N1B0.9037 (2)0.13316 (15)0.20430 (13)0.0495 (5)
N2B0.5847 (2)0.12074 (14)0.44403 (12)0.0470 (5)
H2B0.66980.11190.43920.056*
N3B0.3573 (2)0.12625 (14)0.54523 (13)0.0469 (5)
H3B0.31420.13350.50740.056*
N4B0.5335 (2)0.10497 (15)0.59801 (13)0.0496 (5)
C1B0.8763 (3)0.13635 (17)0.12602 (16)0.0501 (7)
C2B0.7451 (3)0.14426 (17)0.12605 (16)0.0477 (6)
C3B0.6372 (3)0.14685 (17)0.20741 (16)0.0454 (6)
C4B0.6659 (3)0.13928 (16)0.28656 (15)0.0423 (6)
C5B0.8017 (3)0.13273 (17)0.28661 (16)0.0449 (6)
C6B0.5526 (3)0.13693 (17)0.36914 (16)0.0466 (6)
C7B0.4930 (3)0.11702 (16)0.52847 (16)0.0439 (6)
C8B0.3012 (3)0.12150 (17)0.63690 (16)0.0454 (6)
C9B0.1684 (3)0.1288 (2)0.69188 (18)0.0568 (7)
H9B0.09540.13800.67010.068*
C10B0.1500 (3)0.1216 (2)0.78080 (19)0.0612 (8)
H10B0.06200.12630.82020.073*
C11B0.2572 (3)0.1078 (2)0.81315 (18)0.0589 (7)
H11B0.23980.10370.87390.071*
C12B0.3898 (3)0.09979 (19)0.75866 (17)0.0553 (7)
H12B0.46220.08910.78130.066*
C13B0.4118 (3)0.10834 (17)0.66814 (16)0.0446 (6)
C14B1.0427 (3)0.1290 (2)0.20801 (19)0.0586 (7)
H14D1.03690.16650.25870.070*
H14C1.09530.15920.15550.070*
C15B1.1158 (3)0.0272 (2)0.2143 (2)0.0689 (8)
H15D1.12630.00960.16220.083*
H15C1.06190.00420.26540.083*
C16B1.2553 (4)0.0263 (3)0.2224 (3)0.1056 (13)
H16F1.30740.05990.17330.158*
H16E1.30200.03990.22280.158*
H16D1.24470.05840.27640.158*
C17B0.7118 (3)0.1451 (2)0.04263 (18)0.0646 (8)
C18B0.5741 (4)0.2295 (3)0.0391 (2)0.1005 (12)
H18D0.64410.19660.09010.121*
H18C0.54830.29690.05460.121*
C19B0.4490 (4)0.1798 (3)0.0134 (3)0.1195 (15)
H19F0.47500.11300.00150.179*
H19E0.41460.18220.06220.179*
H19D0.37930.21320.03650.179*
C20B0.9947 (3)0.1321 (2)0.04247 (17)0.0620 (8)
H20F0.96280.13390.00740.093*
H20E1.05930.07270.04070.093*
H20D1.03790.18690.04060.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.101 (5)0.156 (5)0.125 (5)0.011 (4)0.047 (4)0.017 (4)
C10.079 (5)0.173 (8)0.062 (5)0.006 (6)0.039 (4)0.014 (5)
O20.098 (2)0.142 (2)0.0954 (19)0.0334 (19)0.0382 (16)0.0141 (17)
C20.130 (4)0.168 (4)0.140 (4)0.030 (3)0.088 (4)0.005 (4)
C30.123 (4)0.218 (5)0.106 (3)0.073 (4)0.055 (3)0.036 (4)
O1A0.0518 (13)0.0949 (14)0.0495 (11)0.0165 (11)0.0226 (9)0.0021 (11)
O2A0.0486 (11)0.0806 (12)0.0461 (11)0.0094 (10)0.0201 (9)0.0013 (9)
O3A0.0469 (12)0.0902 (14)0.0488 (11)0.0154 (10)0.0135 (9)0.0049 (9)
O4A0.165 (3)0.1181 (19)0.0764 (16)0.0805 (19)0.0612 (17)0.0487 (15)
O5A0.0851 (15)0.0796 (13)0.0487 (11)0.0282 (12)0.0345 (11)0.0049 (9)
N1A0.0458 (14)0.0497 (12)0.0455 (13)0.0111 (10)0.0133 (11)0.0000 (9)
N2A0.0455 (14)0.0633 (13)0.0397 (13)0.0116 (11)0.0144 (11)0.0010 (10)
N3A0.0497 (15)0.0588 (13)0.0433 (13)0.0082 (11)0.0163 (11)0.0026 (10)
N4A0.0543 (15)0.0599 (13)0.0421 (13)0.0104 (11)0.0166 (11)0.0010 (10)
C1A0.0564 (18)0.0459 (14)0.0375 (14)0.0170 (13)0.0117 (13)0.0006 (11)
C2A0.0608 (19)0.0454 (14)0.0415 (15)0.0173 (13)0.0183 (14)0.0031 (11)
C3A0.0476 (17)0.0447 (14)0.0473 (15)0.0126 (12)0.0177 (13)0.0001 (11)
C4A0.0479 (17)0.0436 (13)0.0410 (14)0.0095 (12)0.0149 (12)0.0006 (11)
C5A0.0421 (16)0.0444 (14)0.0434 (15)0.0084 (12)0.0138 (13)0.0007 (11)
C6A0.0456 (17)0.0496 (14)0.0459 (16)0.0090 (12)0.0150 (13)0.0013 (11)
C7A0.0462 (17)0.0444 (14)0.0447 (16)0.0107 (12)0.0132 (13)0.0017 (11)
C8A0.0530 (18)0.0456 (14)0.0432 (15)0.0104 (13)0.0061 (14)0.0014 (11)
C9A0.0568 (19)0.0632 (17)0.0613 (19)0.0146 (15)0.0148 (16)0.0011 (14)
C10A0.065 (2)0.0574 (17)0.0575 (19)0.0117 (15)0.0001 (17)0.0017 (14)
C11A0.074 (2)0.0570 (17)0.0461 (17)0.0107 (16)0.0081 (17)0.0026 (13)
C12A0.074 (2)0.0584 (16)0.0443 (16)0.0114 (15)0.0167 (16)0.0019 (13)
C13A0.0531 (18)0.0440 (14)0.0440 (15)0.0084 (12)0.0120 (14)0.0005 (11)
C14A0.0465 (17)0.0657 (17)0.0585 (17)0.0180 (14)0.0133 (14)0.0005 (13)
C15A0.058 (2)0.075 (2)0.079 (2)0.0153 (16)0.0236 (17)0.0028 (16)
C16A0.052 (2)0.118 (3)0.120 (3)0.019 (2)0.029 (2)0.000 (2)
C17A0.074 (2)0.0634 (17)0.0479 (17)0.0168 (16)0.0222 (16)0.0069 (14)
C18A0.118 (3)0.130 (3)0.057 (2)0.022 (3)0.051 (2)0.003 (2)
C19A0.152 (9)0.124 (8)0.090 (7)0.065 (7)0.076 (6)0.003 (6)
C19C0.135 (17)0.103 (16)0.107 (16)0.062 (14)0.089 (14)0.021 (13)
C19D0.103 (15)0.21 (2)0.097 (13)0.015 (16)0.075 (12)0.031 (14)
C20A0.065 (2)0.0704 (18)0.0517 (17)0.0201 (16)0.0096 (15)0.0001 (14)
O1B0.0506 (13)0.1019 (15)0.0473 (11)0.0132 (11)0.0191 (9)0.0058 (11)
O2B0.0503 (12)0.0938 (14)0.0428 (11)0.0131 (10)0.0158 (9)0.0005 (10)
O3B0.0459 (12)0.0921 (14)0.0451 (11)0.0093 (10)0.0110 (9)0.0031 (9)
O4B0.135 (2)0.124 (2)0.0706 (16)0.0405 (18)0.0494 (16)0.0471 (15)
O5B0.0963 (17)0.0793 (14)0.0563 (12)0.0021 (13)0.0361 (12)0.0090 (10)
N1B0.0418 (13)0.0587 (13)0.0433 (13)0.0083 (10)0.0079 (10)0.0002 (10)
N2B0.0383 (12)0.0632 (13)0.0355 (12)0.0065 (10)0.0078 (10)0.0026 (10)
N3B0.0404 (13)0.0600 (13)0.0396 (12)0.0076 (10)0.0125 (10)0.0022 (9)
N4B0.0455 (14)0.0619 (13)0.0379 (12)0.0119 (11)0.0075 (11)0.0014 (10)
C1B0.060 (2)0.0448 (14)0.0390 (15)0.0048 (13)0.0100 (13)0.0027 (11)
C2B0.0543 (18)0.0487 (14)0.0363 (14)0.0011 (13)0.0143 (13)0.0012 (11)
C3B0.0486 (17)0.0464 (14)0.0410 (15)0.0072 (12)0.0149 (13)0.0016 (11)
C4B0.0495 (17)0.0408 (13)0.0340 (13)0.0077 (12)0.0101 (12)0.0016 (10)
C5B0.0411 (16)0.0509 (15)0.0390 (15)0.0064 (12)0.0092 (13)0.0009 (11)
C6B0.0485 (18)0.0477 (14)0.0418 (15)0.0068 (13)0.0128 (13)0.0038 (11)
C7B0.0437 (16)0.0440 (14)0.0405 (15)0.0096 (12)0.0079 (13)0.0020 (11)
C8B0.0459 (16)0.0456 (14)0.0405 (14)0.0082 (12)0.0083 (13)0.0015 (11)
C9B0.0425 (17)0.0750 (18)0.0515 (17)0.0170 (14)0.0100 (14)0.0013 (14)
C10B0.0529 (19)0.0715 (18)0.0512 (18)0.0178 (15)0.0016 (15)0.0046 (14)
C11B0.066 (2)0.0674 (17)0.0369 (15)0.0182 (15)0.0051 (15)0.0001 (13)
C12B0.0562 (19)0.0634 (17)0.0446 (16)0.0141 (14)0.0119 (14)0.0017 (13)
C13B0.0489 (17)0.0452 (14)0.0363 (14)0.0100 (12)0.0082 (13)0.0024 (11)
C14B0.0518 (17)0.0687 (18)0.0515 (16)0.0154 (15)0.0090 (14)0.0001 (13)
C15B0.057 (2)0.078 (2)0.067 (2)0.0133 (16)0.0121 (16)0.0038 (15)
C16B0.059 (2)0.123 (3)0.138 (4)0.021 (2)0.037 (2)0.014 (3)
C17B0.068 (2)0.081 (2)0.0361 (16)0.0040 (18)0.0108 (15)0.0032 (15)
C18B0.126 (3)0.118 (3)0.062 (2)0.001 (2)0.051 (2)0.012 (2)
C19B0.140 (4)0.147 (4)0.101 (3)0.032 (3)0.077 (3)0.013 (3)
C20B0.062 (2)0.0698 (18)0.0427 (16)0.0084 (15)0.0031 (14)0.0028 (13)
Geometric parameters (Å, º) top
O1—C11.4313 (10)C18A—H18H0.9700
O1—H10.8200C19A—H19A0.9600
C1—C1i1.500 (14)C19A—H19B0.9600
C1—H130.9600C19A—H19C0.9600
C1—H120.9601C19C—H19G0.9600
C1—H110.9599C19C—H19H0.9600
O2—C21.428 (6)C19C—H19I0.9600
O2—H20.8200C19D—H19J0.9600
C2—C31.537 (7)C19D—H19K0.9600
C2—H220.9700C19D—H19L0.9600
C2—H210.9700C20A—H20C0.9600
C3—H330.9600C20A—H20B0.9600
C3—H320.9600C20A—H20A0.9600
C3—H310.9600O1B—C3B1.310 (3)
O1A—C3A1.316 (3)O1B—H1B0.8200
O1A—H1A0.8200O2B—C5B1.250 (3)
O2A—C5A1.240 (3)O3B—C6B1.256 (3)
O3A—C6A1.252 (3)O4B—C17B1.191 (3)
O4A—C17A1.205 (3)O5B—C17B1.319 (4)
O5A—C17A1.322 (3)O5B—C18B1.461 (4)
O5A—C18A1.444 (3)N1B—C1B1.373 (3)
N1A—C1A1.364 (3)N1B—C5B1.405 (3)
N1A—C5A1.411 (3)N1B—C14B1.478 (3)
N1A—C14A1.486 (3)N2B—C6B1.345 (3)
N2A—C6A1.345 (3)N2B—C7B1.388 (3)
N2A—C7A1.380 (3)N2B—H2B0.8600
N2A—H2A0.8600N3B—C7B1.350 (3)
N3A—C7A1.349 (3)N3B—C8B1.396 (3)
N3A—C8A1.391 (3)N3B—H3B0.8600
N3A—H3A0.8600N4B—C7B1.309 (3)
N4A—C7A1.318 (3)N4B—C13B1.399 (3)
N4A—C13A1.390 (3)C1B—C2B1.367 (4)
C1A—C2A1.371 (4)C1B—C20B1.499 (4)
C1A—C20A1.499 (4)C2B—C3B1.421 (3)
C2A—C3A1.415 (4)C2B—C17B1.488 (4)
C2A—C17A1.493 (4)C3B—C4B1.391 (3)
C3A—C4A1.399 (3)C4B—C5B1.418 (4)
C4A—C5A1.417 (3)C4B—C6B1.470 (3)
C4A—C6A1.466 (4)C8B—C9B1.378 (4)
C8A—C13A1.388 (4)C8B—C13B1.391 (4)
C8A—C9A1.395 (4)C9B—C10B1.375 (4)
C9A—C10A1.386 (4)C9B—H9B0.9300
C9A—H9A0.9300C10B—C11B1.368 (4)
C10A—C11A1.381 (4)C10B—H10B0.9300
C10A—H10A0.9300C11B—C12B1.373 (4)
C11A—C12A1.368 (4)C11B—H11B0.9300
C11A—H11A0.9300C12B—C13B1.394 (3)
C12A—C13A1.398 (4)C12B—H12B0.9300
C12A—H12A0.9300C14B—C15B1.494 (4)
C14A—C15A1.502 (4)C14B—H14D0.9700
C14A—H14B0.9700C14B—H14C0.9700
C14A—H14A0.9700C15B—C16B1.516 (4)
C15A—C16A1.499 (4)C15B—H15D0.9700
C15A—H15B0.9700C15B—H15C0.9700
C15A—H15A0.9700C16B—H16F0.9600
C16A—H16C0.9600C16B—H16E0.9600
C16A—H16B0.9600C16B—H16D0.9600
C16A—H16A0.9600C18B—C19B1.539 (6)
C18A—C19A1.5390 (10)C18B—H18D0.9700
C18A—C19D1.5396 (11)C18B—H18C0.9700
C18A—C19C1.5396 (11)C19B—H19F0.9600
C18A—H18A0.9700C19B—H19E0.9600
C18A—H18B0.9700C19B—H19D0.9600
C18A—H18E0.9700C20B—H20F0.9600
C18A—H18F0.9700C20B—H20E0.9600
C18A—H18G0.9700C20B—H20D0.9600
C1—O1—H1107.4H18A—C18A—H18G76.3
O1—C1—C1i126.6 (9)H18F—C18A—H18G68.3
O1—C1—H13109.2O5A—C18A—H18H110.4
O1—C1—H12110.2C19D—C18A—H18H110.4
C1i—C1—H12101.3C19C—C18A—H18H69.3
H13—C1—H12109.5H18A—C18A—H18H133.8
O1—C1—H11109.0H18B—C18A—H18H76.6
C1i—C1—H1199.1H18E—C18A—H18H137.0
H13—C1—H11109.5H18G—C18A—H18H108.6
H12—C1—H11109.5C18A—C19A—H19A109.5
C2—O2—H2109.5C18A—C19A—H19B109.5
O2—C2—C3113.5 (3)H19A—C19A—H19B109.5
O2—C2—H22108.9C18A—C19A—H19C109.5
C3—C2—H22108.9H19A—C19A—H19C109.5
O2—C2—H21108.9H19B—C19A—H19C109.5
C3—C2—H21108.9C18A—C19C—H19G109.5
H22—C2—H21107.7C18A—C19C—H19H109.5
C2—C3—H33109.5H19G—C19C—H19H109.5
C2—C3—H32109.5C18A—C19C—H19I109.5
H33—C3—H32109.5H19G—C19C—H19I109.5
C2—C3—H31109.5H19H—C19C—H19I109.5
H33—C3—H31109.5C18A—C19D—H19J109.5
H32—C3—H31109.5C18A—C19D—H19K109.5
C3A—O1A—H1A109.5H19J—C19D—H19K109.5
C17A—O5A—C18A116.9 (2)C18A—C19D—H19L109.5
C1A—N1A—C5A122.9 (2)H19J—C19D—H19L109.5
C1A—N1A—C14A122.5 (2)H19K—C19D—H19L109.5
C5A—N1A—C14A114.6 (2)C1A—C20A—H20C109.5
C6A—N2A—C7A126.5 (2)C1A—C20A—H20B109.5
C6A—N2A—H2A116.8H20C—C20A—H20B109.5
C7A—N2A—H2A116.8C1A—C20A—H20A109.5
C7A—N3A—C8A105.9 (2)H20C—C20A—H20A109.5
C7A—N3A—H3A127.1H20B—C20A—H20A109.5
C8A—N3A—H3A127.1C3B—O1B—H1B109.5
C7A—N4A—C13A103.8 (2)C17B—O5B—C18B116.8 (2)
N1A—C1A—C2A120.2 (2)C1B—N1B—C5B122.4 (2)
N1A—C1A—C20A117.2 (2)C1B—N1B—C14B122.4 (2)
C2A—C1A—C20A122.6 (2)C5B—N1B—C14B115.2 (2)
C1A—C2A—C3A119.7 (2)C6B—N2B—C7B126.0 (2)
C1A—C2A—C17A120.8 (2)C6B—N2B—H2B117.0
C3A—C2A—C17A119.4 (3)C7B—N2B—H2B117.0
O1A—C3A—C4A122.0 (2)C7B—N3B—C8B105.7 (2)
O1A—C3A—C2A118.0 (2)C7B—N3B—H3B127.2
C4A—C3A—C2A120.0 (2)C8B—N3B—H3B127.2
C3A—C4A—C5A120.3 (2)C7B—N4B—C13B103.4 (2)
C3A—C4A—C6A118.5 (2)C2B—C1B—N1B120.2 (2)
C5A—C4A—C6A121.2 (2)C2B—C1B—C20B122.4 (2)
O2A—C5A—N1A118.0 (2)N1B—C1B—C20B117.4 (3)
O2A—C5A—C4A125.2 (2)C1B—C2B—C3B119.8 (2)
N1A—C5A—C4A116.8 (2)C1B—C2B—C17B121.8 (2)
O3A—C6A—N2A121.2 (2)C3B—C2B—C17B118.3 (3)
O3A—C6A—C4A121.2 (2)O1B—C3B—C4B122.8 (2)
N2A—C6A—C4A117.6 (2)O1B—C3B—C2B117.3 (2)
N4A—C7A—N3A114.5 (2)C4B—C3B—C2B119.8 (2)
N4A—C7A—N2A121.1 (2)C3B—C4B—C5B120.3 (2)
N3A—C7A—N2A124.4 (2)C3B—C4B—C6B118.3 (2)
C13A—C8A—N3A105.5 (2)C5B—C4B—C6B121.4 (2)
C13A—C8A—C9A123.1 (2)O2B—C5B—N1B117.9 (2)
N3A—C8A—C9A131.4 (3)O2B—C5B—C4B124.8 (2)
C10A—C9A—C8A115.6 (3)N1B—C5B—C4B117.3 (2)
C10A—C9A—H9A122.2O3B—C6B—N2B121.9 (2)
C8A—C9A—H9A122.2O3B—C6B—C4B121.0 (2)
C11A—C10A—C9A122.1 (3)N2B—C6B—C4B117.1 (2)
C11A—C10A—H10A119.0N4B—C7B—N3B115.3 (2)
C9A—C10A—H10A119.0N4B—C7B—N2B121.6 (2)
C12A—C11A—C10A121.8 (3)N3B—C7B—N2B123.2 (2)
C12A—C11A—H11A119.1C9B—C8B—C13B122.8 (2)
C10A—C11A—H11A119.1C9B—C8B—N3B132.0 (2)
C11A—C12A—C13A118.0 (3)C13B—C8B—N3B105.2 (2)
C11A—C12A—H12A121.0C10B—C9B—C8B116.2 (3)
C13A—C12A—H12A121.0C10B—C9B—H9B121.9
C8A—C13A—N4A110.3 (2)C8B—C9B—H9B121.9
C8A—C13A—C12A119.5 (3)C11B—C10B—C9B122.1 (3)
N4A—C13A—C12A130.2 (3)C11B—C10B—H10B119.0
N1A—C14A—C15A113.3 (2)C9B—C10B—H10B119.0
N1A—C14A—H14B108.9C10B—C11B—C12B122.0 (3)
C15A—C14A—H14B108.9C10B—C11B—H11B119.0
N1A—C14A—H14A108.9C12B—C11B—H11B119.0
C15A—C14A—H14A108.9C11B—C12B—C13B117.4 (3)
H14B—C14A—H14A107.7C11B—C12B—H12B121.3
C16A—C15A—C14A112.1 (3)C13B—C12B—H12B121.3
C16A—C15A—H15B109.2C8B—C13B—C12B119.5 (2)
C14A—C15A—H15B109.2C8B—C13B—N4B110.5 (2)
C16A—C15A—H15A109.2C12B—C13B—N4B130.1 (2)
C14A—C15A—H15A109.2N1B—C14B—C15B112.9 (2)
H15B—C15A—H15A107.9N1B—C14B—H14D109.0
C15A—C16A—H16C109.5C15B—C14B—H14D109.0
C15A—C16A—H16B109.5N1B—C14B—H14C109.0
H16C—C16A—H16B109.5C15B—C14B—H14C109.0
C15A—C16A—H16A109.5H14D—C14B—H14C107.8
H16C—C16A—H16A109.5C14B—C15B—C16B111.3 (3)
H16B—C16A—H16A109.5C14B—C15B—H15D109.4
O4A—C17A—O5A122.9 (3)C16B—C15B—H15D109.4
O4A—C17A—C2A124.1 (3)C14B—C15B—H15C109.4
O5A—C17A—C2A113.0 (2)C16B—C15B—H15C109.4
O5A—C18A—C19A107.5 (5)H15D—C15B—H15C108.0
O5A—C18A—C19D106.6 (6)C15B—C16B—H16F109.5
C19A—C18A—C19D78.2 (10)C15B—C16B—H16E109.5
O5A—C18A—C19C104.9 (8)H16F—C16B—H16E109.5
C19D—C18A—C19C45.0 (10)C15B—C16B—H16D109.5
O5A—C18A—H18A110.2H16F—C16B—H16D109.5
C19A—C18A—H18A110.2H16E—C16B—H16D109.5
C19C—C18A—H18A79.8O4B—C17B—O5B124.5 (3)
O5A—C18A—H18B110.2O4B—C17B—C2B123.6 (3)
C19A—C18A—H18B110.2O5B—C17B—C2B112.0 (2)
C19D—C18A—H18B137.0O5B—C18B—C19B109.9 (3)
C19C—C18A—H18B137.6O5B—C18B—H18D109.7
H18A—C18A—H18B108.5C19B—C18B—H18D109.7
O5A—C18A—H18E110.8O5B—C18B—H18C109.7
C19A—C18A—H18E134.7C19B—C18B—H18C109.7
C19D—C18A—H18E68.4H18D—C18B—H18C108.2
C19C—C18A—H18E110.8C18B—C19B—H19F109.5
H18B—C18A—H18E78.2C18B—C19B—H19E109.5
O5A—C18A—H18F110.8H19F—C19B—H19E109.5
C19A—C18A—H18F78.4C18B—C19B—H19D109.5
C19D—C18A—H18F140.3H19F—C19B—H19D109.5
C19C—C18A—H18F110.8H19E—C19B—H19D109.5
H18A—C18A—H18F132.8C1B—C20B—H20F109.5
H18E—C18A—H18F108.8C1B—C20B—H20E109.5
O5A—C18A—H18G110.4H20F—C20B—H20E109.5
C19A—C18A—H18G136.2C1B—C20B—H20D109.5
C19D—C18A—H18G110.4H20F—C20B—H20D109.5
C19C—C18A—H18G142.4H20E—C20B—H20D109.5
C5A—N1A—C1A—C2A3.5 (3)C17A—O5A—C18A—C19C139.4 (9)
C14A—N1A—C1A—C2A174.5 (2)C5B—N1B—C1B—C2B3.3 (3)
C5A—N1A—C1A—C20A175.7 (2)C14B—N1B—C1B—C2B177.2 (2)
C14A—N1A—C1A—C20A6.2 (3)C5B—N1B—C1B—C20B177.4 (2)
N1A—C1A—C2A—C3A1.2 (3)C14B—N1B—C1B—C20B2.0 (3)
C20A—C1A—C2A—C3A178.0 (2)N1B—C1B—C2B—C3B1.5 (4)
N1A—C1A—C2A—C17A176.1 (2)C20B—C1B—C2B—C3B179.3 (2)
C20A—C1A—C2A—C17A4.7 (4)N1B—C1B—C2B—C17B178.2 (2)
C1A—C2A—C3A—O1A176.3 (2)C20B—C1B—C2B—C17B2.6 (4)
C17A—C2A—C3A—O1A1.0 (3)C1B—C2B—C3B—O1B178.8 (2)
C1A—C2A—C3A—C4A1.1 (3)C17B—C2B—C3B—O1B2.0 (4)
C17A—C2A—C3A—C4A178.3 (2)C1B—C2B—C3B—C4B1.3 (4)
O1A—C3A—C4A—C5A176.2 (2)C17B—C2B—C3B—C4B175.5 (2)
C2A—C3A—C4A—C5A1.0 (3)O1B—C3B—C4B—C5B179.8 (2)
O1A—C3A—C4A—C6A1.4 (3)C2B—C3B—C4B—C5B2.4 (3)
C2A—C3A—C4A—C6A178.6 (2)O1B—C3B—C4B—C6B0.6 (3)
C1A—N1A—C5A—O2A177.9 (2)C2B—C3B—C4B—C6B176.8 (2)
C14A—N1A—C5A—O2A3.9 (3)C1B—N1B—C5B—O2B178.1 (2)
C1A—N1A—C5A—C4A3.4 (3)C14B—N1B—C5B—O2B1.4 (3)
C14A—N1A—C5A—C4A174.7 (2)C1B—N1B—C5B—C4B2.2 (3)
C3A—C4A—C5A—O2A179.6 (2)C14B—N1B—C5B—C4B178.3 (2)
C6A—C4A—C5A—O2A2.1 (4)C3B—C4B—C5B—O2B179.0 (2)
C3A—C4A—C5A—N1A1.1 (3)C6B—C4B—C5B—O2B1.8 (4)
C6A—C4A—C5A—N1A176.44 (19)C3B—C4B—C5B—N1B0.7 (3)
C7A—N2A—C6A—O3A0.7 (4)C6B—C4B—C5B—N1B178.46 (19)
C7A—N2A—C6A—C4A178.2 (2)C7B—N2B—C6B—O3B1.2 (4)
C3A—C4A—C6A—O3A3.1 (3)C7B—N2B—C6B—C4B179.1 (2)
C5A—C4A—C6A—O3A179.3 (2)C3B—C4B—C6B—O3B5.5 (3)
C3A—C4A—C6A—N2A175.7 (2)C5B—C4B—C6B—O3B175.4 (2)
C5A—C4A—C6A—N2A1.9 (3)C3B—C4B—C6B—N2B174.2 (2)
C13A—N4A—C7A—N3A0.3 (3)C5B—C4B—C6B—N2B5.0 (3)
C13A—N4A—C7A—N2A179.0 (2)C13B—N4B—C7B—N3B1.2 (3)
C8A—N3A—C7A—N4A0.3 (3)C13B—N4B—C7B—N2B178.3 (2)
C8A—N3A—C7A—N2A179.0 (2)C8B—N3B—C7B—N4B1.2 (3)
C6A—N2A—C7A—N4A177.6 (2)C8B—N3B—C7B—N2B178.3 (2)
C6A—N2A—C7A—N3A1.0 (4)C6B—N2B—C7B—N4B177.0 (2)
C7A—N3A—C8A—C13A0.2 (2)C6B—N2B—C7B—N3B2.4 (4)
C7A—N3A—C8A—C9A178.7 (3)C7B—N3B—C8B—C9B178.3 (3)
C13A—C8A—C9A—C10A0.3 (4)C7B—N3B—C8B—C13B0.7 (2)
N3A—C8A—C9A—C10A178.0 (2)C13B—C8B—C9B—C10B0.4 (4)
C8A—C9A—C10A—C11A0.5 (4)N3B—C8B—C9B—C10B179.3 (2)
C9A—C10A—C11A—C12A0.0 (4)C8B—C9B—C10B—C11B0.2 (4)
C10A—C11A—C12A—C13A0.6 (4)C9B—C10B—C11B—C12B0.3 (4)
N3A—C8A—C13A—N4A0.0 (3)C10B—C11B—C12B—C13B1.3 (4)
C9A—C8A—C13A—N4A178.7 (2)C9B—C8B—C13B—C12B1.5 (4)
N3A—C8A—C13A—C12A178.9 (2)N3B—C8B—C13B—C12B179.4 (2)
C9A—C8A—C13A—C12A0.2 (4)C9B—C8B—C13B—N4B179.1 (2)
C7A—N4A—C13A—C8A0.2 (3)N3B—C8B—C13B—N4B0.0 (3)
C7A—N4A—C13A—C12A179.0 (2)C11B—C12B—C13B—C8B1.9 (4)
C11A—C12A—C13A—C8A0.7 (4)C11B—C12B—C13B—N4B178.8 (2)
C11A—C12A—C13A—N4A178.0 (2)C7B—N4B—C13B—C8B0.7 (3)
C1A—N1A—C14A—C15A97.7 (3)C7B—N4B—C13B—C12B180.0 (2)
C5A—N1A—C14A—C15A84.2 (3)C1B—N1B—C14B—C15B94.4 (3)
N1A—C14A—C15A—C16A174.8 (3)C5B—N1B—C14B—C15B85.0 (3)
C18A—O5A—C17A—O4A6.0 (5)N1B—C14B—C15B—C16B177.3 (3)
C18A—O5A—C17A—C2A174.9 (3)C18B—O5B—C17B—O4B7.1 (5)
C1A—C2A—C17A—O4A47.2 (4)C18B—O5B—C17B—C2B172.5 (3)
C3A—C2A—C17A—O4A130.0 (3)C1B—C2B—C17B—O4B59.4 (4)
C1A—C2A—C17A—O5A131.9 (3)C3B—C2B—C17B—O4B117.4 (4)
C3A—C2A—C17A—O5A50.9 (3)C1B—C2B—C17B—O5B121.0 (3)
C17A—O5A—C18A—C19A175.1 (5)C3B—C2B—C17B—O5B62.3 (3)
C17A—O5A—C18A—C19D92.5 (11)C17B—O5B—C18B—C19B84.1 (4)
Symmetry code: (i) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O3A0.821.772.503 (2)149
O1B—H1B···O3B0.821.782.508 (2)148
N2A—H2A···O2A0.861.882.600 (3)140
N2B—H2B···O2B0.861.882.596 (3)139
N3A—H3A···O2ii0.862.342.968 (3)130
N3A—H3A···O3A0.862.212.710 (3)117
N3B—H3B···O1iii0.862.463.106 (6)132
N3B—H3B···O3B0.862.182.691 (3)118
O2—H2···N4A0.822.272.926 (3)138
O1—H1···N4B0.822.353.050 (6)144
Symmetry codes: (ii) x+2, y+1, z; (iii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula4C20H22N4O5·2C2H6O·CH4O
Mr1717.84
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.5527 (4), 13.9720 (4), 16.0242 (5)
α, β, γ (°)86.804 (3), 70.980 (3), 78.652 (3)
V3)2189.90 (12)
Z1
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.40 × 0.30 × 0.10
Data collection
DiffractometerOxford Diffraction Xcalibur3
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
23866, 7499, 3785
Rint0.030
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.170, 0.89
No. of reflections7499
No. of parameters596
No. of restraints9
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.44, 0.35

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXTL (Sheldrick, 2008), XP (Bruker, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O3A0.821.772.503 (2)148.5
O1B—H1B···O3B0.821.782.508 (2)147.9
N2A—H2A···O2A0.861.882.600 (3)139.6
N2B—H2B···O2B0.861.882.596 (3)139.0
N3A—H3A···O2i0.862.342.968 (3)129.7
N3A—H3A···O3A0.862.212.710 (3)116.6
N3B—H3B···O1ii0.862.463.106 (6)132.4
N3B—H3B···O3B0.862.182.691 (3)117.8
O2—H2···N4A0.822.272.926 (3)137.5
O1—H1···N4B0.822.353.050 (6)144.2
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y, z+1.
 

References

First citationBruker (1998). XP. Bruker AXS Inc., Karlsruhe, Germany.  Google Scholar
First citationBürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767–784. Weinheim: VCH.  Google Scholar
First citationLow, J. N. & Wilson, C. C. (1983). Acta Cryst. C39, 1688–1690.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationOxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationUkrainets, I. V., Bezugly, P. A., Gorokhova, O. V., Treskach, V. I. & Turov, A. V. (1993). Khim. Geterotsikl. Soedin. pp. 105–108.  Google Scholar
First citationUkrainets, I. V., Sidorenko, L. V., Gorokhova, O. V. & Shishkin, O. V. (2006). Khim. Geterotsikl. Soedin. pp. 217–223.  Google Scholar

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