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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1247.
Published online 2010 September 11. doi:  10.1107/S1600536810034720
PMCID: PMC2983145

7-(1,3-Dioxolan-2-ylmethyl)-1,3-di­methyl-2,6-dioxo-2,3,6,7-tetra­hydro-1H-purin-9-ium tetra­chloridoferrate(III)

Abstract

The asymmetric unit of the title compound, (C11H15N4O4)[FeCl4], contains two independent protonated 7-(1,3-dioxolan-2-ylmeth­yl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione (doxofyllinium) and two tetrahedral tetra­chlorido­ferrate(III) anions. In the doxofyllinium, two disordered methyl­ene C atoms are observed in each dioxolane ring with an occupancy ratio of 0.54 (4):0.46 (4). In the crystal, mol­ecules are connected by N—H(...)O hydrogen bonds and weak C—H(...)O and C—H(...)Cl inter­actions.

Related literature

For the biological activity of the drug doxofylline, see: Franzone et al. (1981 [triangle], 1989 [triangle]); Zhao & Li (2001 [triangle]). For bond distances and angles in other tetra­chlorido­ferrate(III) compounds, see: Barbaro et al. (1992 [triangle]); Bottomley et al. (1984 [triangle]). For the synthesis of doxofylline, see: Li et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1247-scheme1.jpg

Experimental

Crystal data

  • (C11H15N4O4)[FeCl4]
  • M r = 464.92
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-66-m1247-efi1.jpg
  • a = 20.2947 (4) Å
  • c = 9.0692 (4) Å
  • V = 3735.38 (19) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.40 mm−1
  • T = 293 K
  • 0.27 × 0.16 × 0.13 mm

Data collection

  • Bruker SMART APEX area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.775, T max = 0.852
  • 19874 measured reflections
  • 6253 independent reflections
  • 5589 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.099
  • wR(F 2) = 0.207
  • S = 1.30
  • 6253 reflections
  • 447 parameters
  • 13 restraints
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.31 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2724 Friedel pairs
  • Flack parameter: 0.10 (4)

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034720/jh2188sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034720/jh2188Isup2.hkl

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

Acknowledgments

We are grateful for financial support by the Natural Science Foundation of Tibet (2009–10–12) and the Natural Science Foundation of the Key Laboratory of Resource Biology and Biotechnology in Western China (Northwest University), Ministry of Education (2009–11–12).

supplementary crystallographic information

Comment

Doxofylline [7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-3,7- dihydro-1H-purine-2,6-dione] is a xanthine drug with anti-asthmatic (Franzone et al., 1989), antiinflammatory (Zhao et al., 2001), and bronchodilating activities (Franzone et al., 1981). Now we present here the structure of the title compound, (I).

In the title compound (Fig. 1), (I), the asymmetric unit contain two crystallographically independent molecules of doxofyllinium tetrachloroferrate(III). The furan rings of the doxofyllinium are disordered, and the five atoms of these rings aren't coplanar. The iron cation is tetra coordinated by chlorine anions, and it adopts a slightly distorted tetrahedral coordination with two angles smaller than the tetrahedral one, two almost equal to tetrahedral and two larger than tetrahedral (Table 1). Fe—Cl distances spanning the range 2.172 (3) Å-2.190 (4) Å, and Cl—Fe—Cl angles 107.41 (16)°-111.77 (15)°, are similar to those found in other tetrachloroferrate(III) (Bottomley et al., 1984; Barbaro et al., 1992).

In the crystal, doxofyllinium cations are linked by N8—H8···O6i and N4—H4···O2ii hydrogen bonds (Table 2). The weak C—H···O and C—H···Cl interactions further link (I), reinforcing the structure (Table 2).

Experimental

Doxofylline was synthesized according to Li et al. (1995). Doxofylline, hydrochloric acid and trichloride were dissolved in sufficient ethanol by heating to 333 K, where a yellow solution resulted. Crystals of (I) were formed by gradual evaporation of ethanol over a period of one week are 293 K.

Refinement

All of the H atoms were placed in calculated positions and allowed to ride on their parent atoms at distances of 0.93 (C5—H5), 0.96 (methyl), 0.97 (methylene) and 0.98Å (methine), with Uiso(H) = 1.2–1.5 Ueq(C).

Figures

Fig. 1.
A view of the asymmetric unit of (I) with atom labels, showing 40% probability displacement ellipsoids. Parts of disorder furan rings are omitted for clarity.

Crystal data

(C11H15N4O4)[FeCl4]Dx = 1.653 Mg m3
Mr = 464.92Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42Cell parameters from 8917 reflections
Hall symbol: P 4cθ = 2.2–26.5°
a = 20.2947 (4) ŵ = 1.40 mm1
c = 9.0692 (4) ÅT = 293 K
V = 3735.38 (19) Å3Block, colourless
Z = 80.27 × 0.16 × 0.13 mm
F(000) = 1880.0

Data collection

Bruker SMART APEX area-detector diffractometer6253 independent reflections
Radiation source: fine-focus sealed tube5589 reflections with I > 2σ(I)
graphiteRint = 0.046
[var phi] and ω scanθmax = 25.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −24→23
Tmin = 0.775, Tmax = 0.852k = −24→23
19874 measured reflectionsl = −9→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.099H-atom parameters constrained
wR(F2) = 0.207w = 1/[σ2(Fo2) + (0.0665P)2 + 7.3566P] where P = (Fo2 + 2Fc2)/3
S = 1.30(Δ/σ)max < 0.001
6253 reflectionsΔρmax = 0.49 e Å3
447 parametersΔρmin = −0.31 e Å3
13 restraintsAbsolute structure: Flack (1983), 2724 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.10 (4)

Special details

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)

xyzUiso*/UeqOcc. (<1)
Fe10.68089 (8)0.33071 (7)0.16159 (18)0.0569 (4)
Fe20.16760 (8)0.17898 (7)0.22058 (17)0.0586 (4)
Cl10.69861 (18)0.24505 (16)0.2998 (4)0.0869 (10)
Cl20.59364 (17)0.3131 (2)0.0264 (4)0.0898 (11)
Cl30.76550 (17)0.35346 (18)0.0238 (4)0.0913 (11)
Cl40.6604 (2)0.41656 (17)0.3005 (4)0.0913 (11)
Cl50.17996 (16)0.25893 (15)0.3795 (4)0.0735 (9)
Cl60.1499 (2)0.08671 (15)0.3379 (4)0.0886 (10)
Cl70.08268 (18)0.20197 (19)0.0809 (5)0.0966 (11)
Cl80.25566 (19)0.1697 (2)0.0873 (5)0.1016 (12)
O10.5196 (4)0.1673 (3)0.2934 (8)0.0592 (19)
O20.4364 (3)0.3755 (3)0.2618 (9)0.063 (2)
O30.4982 (4)0.1135 (4)0.6244 (10)0.086 (3)
O40.5648 (4)0.1321 (4)0.8177 (8)0.072 (2)
O50.3355 (3)0.0243 (4)−0.1686 (8)0.0587 (19)
O60.1189 (4)0.0815 (4)−0.2061 (9)0.068 (2)
O70.3705 (4)−0.0319 (3)0.3520 (8)0.063 (2)
O80.3889 (4)0.0414 (4)0.1734 (9)0.073 (2)
N10.4750 (4)0.2704 (4)0.2853 (9)0.0448 (19)
N20.5058 (4)0.3546 (3)0.4494 (9)0.044 (2)
N30.5913 (3)0.2156 (3)0.5737 (8)0.0370 (16)
N40.5845 (4)0.3180 (4)0.6382 (9)0.0450 (19)
H40.59070.35390.68650.054*
N50.2260 (4)0.0565 (4)−0.1796 (9)0.0464 (19)
N60.1468 (4)0.0128 (4)−0.0221 (10)0.047 (2)
N70.2938 (3)−0.0580 (3)0.1018 (8)0.0343 (16)
N80.1903 (4)−0.0635 (3)0.1613 (9)0.0452 (19)
H80.1551−0.07440.20810.054*
C10.5154 (4)0.2206 (4)0.3469 (11)0.040 (2)
C20.4696 (4)0.3359 (5)0.3274 (12)0.046 (2)
C30.5443 (4)0.3099 (3)0.5178 (10)0.0317 (19)
C40.5473 (4)0.2455 (4)0.4781 (10)0.039 (2)
C50.6115 (4)0.2604 (4)0.6661 (11)0.040 (2)
H50.64130.25260.74200.048*
C60.4343 (6)0.2508 (6)0.1589 (13)0.068 (3)
H6A0.44140.20500.13800.103*
H6B0.44630.27660.07440.103*
H6C0.38870.25810.18170.103*
C70.5043 (5)0.4240 (5)0.4975 (16)0.068 (3)
H7A0.47430.44830.43640.102*
H7B0.54760.44260.48940.102*
H7C0.48990.42620.59830.102*
C80.6086 (5)0.1450 (4)0.5793 (11)0.049 (2)
H8A0.65300.14010.61760.059*
H8B0.60770.12680.48050.059*
C90.5614 (6)0.1078 (5)0.6754 (12)0.060 (3)
H90.57390.06110.67620.072*
C100.4622 (13)0.1031 (15)0.7592 (18)0.068 (8)0.46 (4)
H10A0.46590.05800.79390.081*0.46 (4)
H10B0.41600.11470.74880.081*0.46 (4)
C110.4989 (6)0.1514 (14)0.859 (3)0.068 (8)0.46 (4)
H11A0.48950.19690.83450.081*0.46 (4)
H11B0.49010.14360.96270.081*0.46 (4)
C10'0.4559 (11)0.1331 (16)0.7455 (19)0.094 (10)0.54 (4)
H10C0.41570.10720.74790.113*0.54 (4)
H10D0.44480.17950.74010.113*0.54 (4)
C11'0.4999 (7)0.1183 (18)0.878 (3)0.094 (10)0.54 (4)
H11C0.48980.14690.96090.113*0.54 (4)
H11D0.49600.07270.90910.113*0.54 (4)
C120.2815 (5)0.0217 (4)−0.1225 (11)0.043 (2)
C130.1621 (4)0.0531 (4)−0.1418 (12)0.044 (2)
C140.1953 (4)−0.0211 (3)0.0451 (10)0.0309 (19)
C150.2591 (4)−0.0156 (4)0.0084 (10)0.035 (2)
C160.2515 (5)−0.0846 (4)0.1871 (11)0.042 (2)
H160.2622−0.11530.25930.050*
C170.2421 (6)0.1030 (6)−0.3009 (13)0.080 (4)
H17A0.28870.1019−0.31960.119*
H17B0.22940.1468−0.27310.119*
H17C0.21880.0902−0.38850.119*
C180.0772 (5)0.0074 (6)0.0225 (16)0.071 (4)
H18A0.05070.0353−0.03890.107*
H18B0.07260.02070.12350.107*
H18C0.0629−0.03750.01190.107*
C190.3647 (4)−0.0690 (5)0.1035 (11)0.045 (2)
H19A0.3825−0.06100.00580.054*
H19B0.3736−0.11450.12920.054*
C200.3981 (4)−0.0246 (5)0.2117 (13)0.054 (3)
H200.4453−0.03470.21530.065*
C220.367 (2)0.0769 (14)0.303 (2)0.065 (11)0.36 (4)
H22A0.32070.08630.29880.078*0.36 (4)
H22B0.39150.11790.31410.078*0.36 (4)
C210.383 (3)0.0292 (8)0.429 (3)0.065 (11)0.36 (4)
H21A0.42890.03270.46060.078*0.36 (4)
H21B0.35430.03530.51270.078*0.36 (4)
C22'0.3901 (12)0.0742 (11)0.3145 (17)0.078 (7)0.64 (4)
H22C0.37180.11830.30760.094*0.64 (4)
H22D0.43460.07690.35300.094*0.64 (4)
C21'0.3470 (14)0.0299 (6)0.411 (3)0.078 (7)0.64 (4)
H21C0.35660.03480.51500.094*0.64 (4)
H21D0.30040.03650.39310.094*0.64 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0695 (10)0.0601 (10)0.0411 (9)−0.0070 (8)0.0035 (8)0.0009 (8)
Fe20.0745 (11)0.0581 (10)0.0432 (9)0.0120 (8)0.0031 (8)0.0023 (8)
Cl10.105 (2)0.078 (2)0.078 (2)0.0085 (18)0.021 (2)0.0265 (19)
Cl20.089 (2)0.126 (3)0.055 (2)−0.026 (2)−0.0054 (17)−0.0144 (19)
Cl30.083 (2)0.096 (2)0.095 (3)−0.0082 (18)0.027 (2)0.032 (2)
Cl40.128 (3)0.082 (2)0.064 (2)0.003 (2)−0.008 (2)−0.0211 (18)
Cl50.087 (2)0.0716 (18)0.0619 (19)−0.0058 (16)0.0210 (17)−0.0146 (15)
Cl60.136 (3)0.0681 (19)0.061 (2)0.0021 (19)−0.004 (2)0.0153 (16)
Cl70.101 (3)0.108 (3)0.081 (2)0.023 (2)−0.027 (2)0.010 (2)
Cl80.102 (3)0.129 (3)0.073 (2)0.011 (2)0.027 (2)−0.018 (2)
O10.090 (5)0.040 (4)0.047 (4)−0.004 (3)−0.018 (4)−0.019 (3)
O20.045 (4)0.064 (4)0.079 (6)0.019 (3)−0.012 (4)0.022 (4)
O30.093 (6)0.087 (6)0.078 (7)−0.033 (5)−0.019 (5)0.002 (5)
O40.086 (5)0.093 (6)0.036 (4)0.012 (4)−0.006 (4)0.013 (4)
O50.035 (4)0.097 (5)0.044 (4)−0.002 (3)0.015 (3)0.027 (4)
O60.065 (5)0.068 (5)0.071 (6)0.020 (4)−0.016 (4)0.017 (4)
O70.098 (6)0.055 (4)0.034 (4)−0.003 (4)−0.015 (4)0.011 (3)
O80.081 (5)0.066 (5)0.073 (6)−0.024 (4)0.002 (5)0.009 (4)
N10.049 (4)0.055 (5)0.031 (4)−0.003 (4)−0.008 (4)0.005 (4)
N20.050 (5)0.024 (4)0.056 (6)0.008 (3)−0.005 (4)0.010 (3)
N30.048 (4)0.041 (4)0.022 (4)0.009 (3)−0.005 (3)0.004 (3)
N40.061 (5)0.036 (4)0.038 (5)0.003 (3)−0.021 (4)−0.014 (3)
N50.061 (5)0.047 (4)0.032 (4)0.010 (4)−0.010 (4)0.009 (4)
N60.035 (4)0.050 (5)0.056 (5)0.005 (3)0.005 (4)0.015 (4)
N70.037 (4)0.039 (4)0.027 (4)0.003 (3)0.002 (3)0.012 (3)
N80.040 (4)0.046 (4)0.049 (5)−0.010 (3)0.013 (4)0.000 (4)
C10.033 (5)0.047 (5)0.040 (6)−0.003 (4)0.004 (4)0.010 (5)
C20.033 (5)0.060 (6)0.044 (6)0.005 (4)−0.009 (4)0.014 (5)
C30.047 (5)0.015 (4)0.033 (5)−0.012 (3)0.009 (4)−0.004 (3)
C40.038 (5)0.052 (6)0.026 (5)−0.007 (4)0.002 (4)0.007 (4)
C50.052 (5)0.035 (5)0.033 (5)0.004 (4)−0.022 (4)0.004 (4)
C60.088 (8)0.071 (7)0.046 (7)0.008 (6)−0.020 (6)−0.001 (6)
C70.060 (7)0.044 (6)0.101 (10)0.008 (5)−0.027 (7)0.001 (6)
C80.065 (6)0.052 (6)0.030 (5)0.018 (5)−0.010 (5)0.003 (4)
C90.096 (9)0.045 (6)0.039 (6)0.006 (5)−0.021 (6)0.010 (5)
C100.057 (13)0.060 (14)0.085 (17)0.011 (9)−0.009 (10)0.043 (12)
C110.057 (13)0.060 (14)0.085 (17)0.011 (9)−0.009 (10)0.043 (12)
C10'0.083 (15)0.061 (16)0.14 (2)0.025 (11)0.014 (14)0.054 (14)
C11'0.083 (15)0.061 (16)0.14 (2)0.025 (11)0.014 (14)0.054 (14)
C120.053 (6)0.035 (5)0.041 (6)−0.004 (4)−0.007 (5)0.005 (4)
C130.026 (4)0.046 (5)0.060 (7)0.017 (4)−0.014 (5)−0.009 (5)
C140.037 (5)0.019 (4)0.037 (5)−0.008 (3)0.006 (4)0.007 (3)
C150.048 (5)0.025 (4)0.032 (5)0.003 (4)0.002 (4)0.002 (4)
C160.061 (6)0.021 (4)0.043 (6)0.007 (4)−0.008 (5)0.018 (4)
C170.096 (9)0.094 (9)0.049 (8)0.012 (7)0.012 (7)0.020 (7)
C180.038 (6)0.072 (7)0.103 (10)0.003 (5)0.003 (6)0.015 (7)
C190.035 (5)0.057 (6)0.042 (6)0.019 (4)−0.008 (4)0.007 (5)
C200.034 (5)0.059 (6)0.069 (8)0.011 (4)0.003 (5)0.015 (6)
C220.06 (2)0.051 (16)0.08 (2)−0.008 (12)0.016 (14)0.002 (14)
C210.06 (2)0.051 (16)0.08 (2)−0.008 (12)0.016 (14)0.002 (14)
C22'0.063 (12)0.064 (11)0.108 (15)−0.001 (7)−0.001 (9)−0.009 (10)
C21'0.063 (12)0.064 (11)0.108 (15)−0.001 (7)−0.001 (9)−0.009 (10)

Geometric parameters (Å, °)

Fe1—Cl12.173 (3)N8—H80.8600
Fe1—Cl32.173 (3)C1—C41.446 (13)
Fe1—Cl22.183 (4)C3—C41.357 (12)
Fe1—Cl42.190 (4)C5—H50.9300
Fe2—Cl82.165 (4)C6—H6A0.9600
Fe2—Cl62.183 (3)C6—H6B0.9600
Fe2—Cl52.185 (3)C6—H6C0.9600
Fe2—Cl72.189 (4)C7—H7A0.9600
O1—C11.189 (10)C7—H7B0.9600
O2—C21.206 (11)C7—H7C0.9600
O3—C91.368 (13)C8—C91.499 (14)
O3—C101.441 (10)C8—H8A0.9700
O3—C10'1.450 (10)C8—H8B0.9700
O4—C91.383 (13)C9—H90.9800
O4—C111.442 (10)C10—C111.528 (10)
O4—C11'1.454 (10)C10—H10A0.9700
O5—C121.173 (10)C10—H10B0.9700
O6—C131.201 (10)C11—H11A0.9700
O7—C201.398 (13)C11—H11B0.9700
O7—C21'1.444 (9)C10'—C11'1.529 (10)
O7—C211.447 (10)C10'—H10C0.9700
O8—C201.396 (12)C10'—H10D0.9700
O8—C22'1.443 (10)C11'—H11C0.9700
O8—C221.446 (10)C11'—H11D0.9700
N1—C21.386 (12)C12—C151.479 (12)
N1—C11.417 (11)C14—C151.342 (11)
N1—C61.467 (13)C16—H160.9300
N2—C31.349 (11)C17—H17A0.9600
N2—C21.382 (12)C17—H17B0.9600
N2—C71.473 (12)C17—H17C0.9600
N3—C51.302 (11)C18—H18A0.9600
N3—C41.384 (11)C18—H18B0.9600
N3—C81.477 (11)C18—H18C0.9600
N4—C51.316 (10)C19—C201.494 (14)
N4—C31.372 (11)C19—H19A0.9700
N4—H40.8600C19—H19B0.9700
N5—C131.344 (11)C20—H200.9800
N5—C121.427 (11)C22—C211.530 (10)
N5—C171.486 (13)C22—H22A0.9700
N6—C141.346 (11)C22—H22B0.9700
N6—C131.394 (13)C21—H21A0.9700
N6—C181.473 (12)C21—H21B0.9700
N7—C161.274 (11)C22'—C21'1.528 (10)
N7—C151.399 (10)C22'—H22C0.9700
N7—C191.456 (10)C22'—H22D0.9700
N8—C161.335 (11)C21'—H21C0.9700
N8—C141.365 (11)C21'—H21D0.9700
Cl1—Fe1—Cl3111.77 (15)O3—C10—C1199.2 (16)
Cl1—Fe1—Cl2109.10 (16)O3—C10—H10A111.9
Cl3—Fe1—Cl2110.66 (17)C11—C10—H10A111.9
Cl1—Fe1—Cl4109.65 (16)O3—C10—H10B111.9
Cl3—Fe1—Cl4108.16 (16)C11—C10—H10B111.9
Cl2—Fe1—Cl4107.41 (16)H10A—C10—H10B109.6
Cl8—Fe2—Cl6109.43 (17)O4—C11—C1097.2 (16)
Cl8—Fe2—Cl5109.77 (15)O4—C11—H11A112.3
Cl6—Fe2—Cl5109.54 (15)C10—C11—H11A112.3
Cl8—Fe2—Cl7110.21 (18)O4—C11—H11B112.3
Cl6—Fe2—Cl7109.58 (17)C10—C11—H11B112.3
Cl5—Fe2—Cl7108.28 (15)H11A—C11—H11B109.9
C9—O3—C10100.2 (14)O3—C10'—C11'101.4 (17)
C9—O3—C10'108.8 (12)O3—C10'—H10C111.5
C10—O3—C10'25.3 (10)C11'—C10'—H10C111.5
C9—O4—C11107.1 (13)O3—C10'—H10D111.5
C9—O4—C11'103.8 (15)C11'—C10'—H10D111.5
C11—O4—C11'27.7 (10)H10C—C10'—H10D109.3
C20—O7—C21'112.1 (10)O4—C11'—C10'101.1 (15)
C20—O7—C21106.0 (16)O4—C11'—H11C111.6
C21'—O7—C2130.3 (14)C10'—C11'—H11C111.6
C20—O8—C22'102.7 (12)O4—C11'—H11D111.6
C20—O8—C22108.4 (14)C10'—C11'—H11D111.6
C22'—O8—C2218.9 (19)H11C—C11'—H11D109.4
C2—N1—C1128.4 (8)O5—C12—N5125.8 (9)
C2—N1—C6115.5 (8)O5—C12—C15126.6 (8)
C1—N1—C6116.1 (8)N5—C12—C15107.5 (8)
C3—N2—C2119.4 (7)O6—C13—N5123.8 (10)
C3—N2—C7121.2 (8)O6—C13—N6119.9 (8)
C2—N2—C7119.3 (8)N5—C13—N6116.3 (7)
C5—N3—C4107.5 (7)C15—C14—N6123.4 (7)
C5—N3—C8125.4 (7)C15—C14—N8108.4 (7)
C4—N3—C8126.9 (7)N6—C14—N8128.2 (7)
C5—N4—C3107.2 (7)C14—C15—N7106.5 (7)
C5—N4—H4126.4C14—C15—C12122.6 (8)
C3—N4—H4126.4N7—C15—C12130.2 (8)
C13—N5—C12130.1 (8)N7—C16—N8112.6 (8)
C13—N5—C17115.8 (8)N7—C16—H16123.7
C12—N5—C17114.1 (8)N8—C16—H16123.7
C14—N6—C13119.3 (7)N5—C17—H17A109.5
C14—N6—C18122.5 (8)N5—C17—H17B109.5
C13—N6—C18118.1 (8)H17A—C17—H17B109.5
C16—N7—C15106.8 (7)N5—C17—H17C109.5
C16—N7—C19126.5 (7)H17A—C17—H17C109.5
C15—N7—C19126.7 (7)H17B—C17—H17C109.5
C16—N8—C14105.6 (7)N6—C18—H18A109.5
C16—N8—H8127.2N6—C18—H18B109.5
C14—N8—H8127.2H18A—C18—H18B109.5
O1—C1—N1122.0 (9)N6—C18—H18C109.5
O1—C1—C4128.4 (9)H18A—C18—H18C109.5
N1—C1—C4109.5 (8)H18B—C18—H18C109.5
O2—C2—N2120.6 (9)N7—C19—C20111.3 (8)
O2—C2—N1123.2 (9)N7—C19—H19A109.4
N2—C2—N1116.2 (8)C20—C19—H19A109.4
N2—C3—C4123.5 (8)N7—C19—H19B109.4
N2—C3—N4129.1 (7)C20—C19—H19B109.4
C4—C3—N4107.4 (7)H19A—C19—H19B108.0
C3—C4—N3106.5 (8)O8—C20—O7105.9 (8)
C3—C4—C1122.3 (8)O8—C20—C19110.7 (9)
N3—C4—C1130.6 (8)O7—C20—C19110.6 (8)
N3—C5—N4111.3 (8)O8—C20—H20109.8
N3—C5—H5124.3O7—C20—H20109.8
N4—C5—H5124.3C19—C20—H20109.8
N1—C6—H6A109.5O8—C22—C21103.2 (18)
N1—C6—H6B109.5O8—C22—H22A111.1
H6A—C6—H6B109.5C21—C22—H22A111.1
N1—C6—H6C109.5O8—C22—H22B111.1
H6A—C6—H6C109.5C21—C22—H22B111.1
H6B—C6—H6C109.5H22A—C22—H22B109.1
N2—C7—H7A109.5O7—C21—C2298.3 (18)
N2—C7—H7B109.5O7—C21—H21A112.1
H7A—C7—H7B109.5C22—C21—H21A112.1
N2—C7—H7C109.5O7—C21—H21B112.1
H7A—C7—H7C109.5C22—C21—H21B112.1
H7B—C7—H7C109.5H21A—C21—H21B109.7
N3—C8—C9110.9 (8)O8—C22'—C21'103.0 (13)
N3—C8—H8A109.5O8—C22'—H22C111.2
C9—C8—H8A109.5C21'—C22'—H22C111.2
N3—C8—H8B109.5O8—C22'—H22D111.2
C9—C8—H8B109.5C21'—C22'—H22D111.2
H8A—C8—H8B108.0H22C—C22'—H22D109.1
O3—C9—O4109.3 (10)O7—C21'—C22'96.4 (14)
O3—C9—C8111.1 (8)O7—C21'—H21C112.5
O4—C9—C8109.3 (9)C22'—C21'—H21C112.5
O3—C9—H9109.0O7—C21'—H21D112.5
O4—C9—H9109.0C22'—C21'—H21D112.5
C8—C9—H9109.0H21C—C21'—H21D110.0

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4···O2i0.861.932.774 (9)165
N8—H8···O6ii0.861.912.754 (9)166
C5—H5···Cl5i0.932.803.650 (11)153
C8—H8B···O7iii0.972.293.114 (11)142
C10—H10C···O5iv0.952.463.098 (11)124
C10'—H10B···O5iv0.892.573.384 (11)153
C10'—H10C···O5iv0.972.463.384 (11)159
C16—H16···Cl1iii0.932.783.560 (11)143
C19—H19A···O4v0.972.483.227 (11)134
C19—H19A···O50.972.533.167 (11)123
C22'—H22D···O10.972.583.242 (11)126

Symmetry codes: (i) −y+1, x, z+1/2; (ii) y, −x, z+1/2; (iii) −x+1, −y, z; (iv) x, y, z+1; (v) −x+1, −y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2188).

References

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