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

Wang, P.P.; Gong, J.; Ni, S.-F.

doi:10.1107/S1600536810034720

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1247

doi:10.1107/S1600536810034720

Open

access

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

Ping Ping Wang,^a Jiang Gong ^b,^c and Shi-Feng Ni ^c ^*

^aCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, ^bDepartment of Medicine, Tibet Nationalities Institute, Xianyang, Shaanxi 712082, People's Republic of China, and ^cKey Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, College of Life Science, Northwest University, Xi'an 710069, People's Republic of China
^*Correspondence e-mail: nshyfe@sina.cn

(Received 20 July 2010; accepted 28 August 2010; online 11 September 2010)

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

Experimental

Crystal data

(C₁₁H₁₅N₄O₄)[FeCl₄]
M_r = 464.92
Tetragonal, P 4₂
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 ) 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[F² > 2σ(F²)] = 0.099
wR(F²) = 0.207
S = 1.30
6253 reflections
447 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ), 2724 Friedel pairs
Flack parameter: 0.10 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O2ⁱ	0.86	1.93	2.774 (9)	165
N8—H8⋯O6ⁱⁱ	0.86	1.91	2.754 (9)	166
C5—H5⋯Cl5ⁱ	0.93	2.80	3.650 (11)	153
C8—H8B⋯O7ⁱⁱⁱ	0.97	2.29	3.114 (11)	142
C10—H10C⋯O5^iv	0.95	2.46	3.098 (11)	124
C10′—H10B⋯O5^iv	0.89	2.57	3.384 (11)	153
C10′—H10C⋯O5^iv	0.97	2.46	3.384 (11)	159
C16—H16⋯Cl1ⁱⁱⁱ	0.93	2.78	3.560 (11)	143
C19—H19A⋯O4^v	0.97	2.48	3.227 (11)	134
C19—H19A⋯O5	0.97	2.53	3.167 (11)	123
C22′—H22D⋯O1	0.97	2.58	3.242 (11)	126
Symmetry codes: (i) $[-y+1, x, z+{\script{1\over 2}}]$ ; (ii) $[y, -x, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, z; (iv) x, y, z+1; (v) -x+1, -y, z-1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: SHELXL97.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXL97 (Sheldrick, 2008).

Figures top

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.

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

Crystal data top

(C₁₁H₁₅N₄O₄)[FeCl₄]	D_x = 1.653 Mg m⁻³
M_r = 464.92	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₂	Cell parameters from 8917 reflections
Hall symbol: P 4c	θ = 2.2–26.5°
a = 20.2947 (4) Å	µ = 1.40 mm⁻¹
c = 9.0692 (4) Å	T = 293 K
V = 3735.38 (19) Å³	Block, colourless
Z = 8	0.27 × 0.16 × 0.13 mm
F(000) = 1880.0

Data collection top

Bruker SMART APEX area-detector diffractometer	6253 independent reflections
Radiation source: fine-focus sealed tube	5589 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scan	θ_max = 25.0°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −24→23
T_min = 0.775, T_max = 0.852	k = −24→23
19874 measured reflections	l = −9→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.099	H-atom parameters constrained
wR(F²) = 0.207	w = 1/[σ²(F_o²) + (0.0665P)² + 7.3566P] where P = (F_o² + 2F_c²)/3
S = 1.30	(Δ/σ)_max < 0.001
6253 reflections	Δρ_max = 0.49 e Å⁻³
447 parameters	Δρ_min = −0.31 e Å⁻³
13 restraints	Absolute structure: Flack (1983), 2724 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.10 (4)

Crystal data top

(C₁₁H₁₅N₄O₄)[FeCl₄]	Z = 8
M_r = 464.92	Mo Kα radiation
Tetragonal, P4₂	µ = 1.40 mm⁻¹
a = 20.2947 (4) Å	T = 293 K
c = 9.0692 (4) Å	0.27 × 0.16 × 0.13 mm
V = 3735.38 (19) Å³

Data collection top

Bruker SMART APEX area-detector diffractometer	6253 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	5589 reflections with I > 2σ(I)
T_min = 0.775, T_max = 0.852	R_int = 0.046
19874 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.099	H-atom parameters constrained
wR(F²) = 0.207	Δρ_max = 0.49 e Å⁻³
S = 1.30	Δρ_min = −0.31 e Å⁻³
6253 reflections	Absolute structure: Flack (1983), 2724 Friedel pairs
447 parameters	Absolute structure parameter: 0.10 (4)
13 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.68089 (8)	0.33071 (7)	0.16159 (18)	0.0569 (4)
Fe2	0.16760 (8)	0.17898 (7)	0.22058 (17)	0.0586 (4)
Cl1	0.69861 (18)	0.24505 (16)	0.2998 (4)	0.0869 (10)
Cl2	0.59364 (17)	0.3131 (2)	0.0264 (4)	0.0898 (11)
Cl3	0.76550 (17)	0.35346 (18)	0.0238 (4)	0.0913 (11)
Cl4	0.6604 (2)	0.41656 (17)	0.3005 (4)	0.0913 (11)
Cl5	0.17996 (16)	0.25893 (15)	0.3795 (4)	0.0735 (9)
Cl6	0.1499 (2)	0.08671 (15)	0.3379 (4)	0.0886 (10)
Cl7	0.08268 (18)	0.20197 (19)	0.0809 (5)	0.0966 (11)
Cl8	0.25566 (19)	0.1697 (2)	0.0873 (5)	0.1016 (12)
O1	0.5196 (4)	0.1673 (3)	0.2934 (8)	0.0592 (19)
O2	0.4364 (3)	0.3755 (3)	0.2618 (9)	0.063 (2)
O3	0.4982 (4)	0.1135 (4)	0.6244 (10)	0.086 (3)
O4	0.5648 (4)	0.1321 (4)	0.8177 (8)	0.072 (2)
O5	0.3355 (3)	0.0243 (4)	−0.1686 (8)	0.0587 (19)
O6	0.1189 (4)	0.0815 (4)	−0.2061 (9)	0.068 (2)
O7	0.3705 (4)	−0.0319 (3)	0.3520 (8)	0.063 (2)
O8	0.3889 (4)	0.0414 (4)	0.1734 (9)	0.073 (2)
N1	0.4750 (4)	0.2704 (4)	0.2853 (9)	0.0448 (19)
N2	0.5058 (4)	0.3546 (3)	0.4494 (9)	0.044 (2)
N3	0.5913 (3)	0.2156 (3)	0.5737 (8)	0.0370 (16)
N4	0.5845 (4)	0.3180 (4)	0.6382 (9)	0.0450 (19)
H4	0.5907	0.3539	0.6865	0.054*
N5	0.2260 (4)	0.0565 (4)	−0.1796 (9)	0.0464 (19)
N6	0.1468 (4)	0.0128 (4)	−0.0221 (10)	0.047 (2)
N7	0.2938 (3)	−0.0580 (3)	0.1018 (8)	0.0343 (16)
N8	0.1903 (4)	−0.0635 (3)	0.1613 (9)	0.0452 (19)
H8	0.1551	−0.0744	0.2081	0.054*
C1	0.5154 (4)	0.2206 (4)	0.3469 (11)	0.040 (2)
C2	0.4696 (4)	0.3359 (5)	0.3274 (12)	0.046 (2)
C3	0.5443 (4)	0.3099 (3)	0.5178 (10)	0.0317 (19)
C4	0.5473 (4)	0.2455 (4)	0.4781 (10)	0.039 (2)
C5	0.6115 (4)	0.2604 (4)	0.6661 (11)	0.040 (2)
H5	0.6413	0.2526	0.7420	0.048*
C6	0.4343 (6)	0.2508 (6)	0.1589 (13)	0.068 (3)
H6A	0.4414	0.2050	0.1380	0.103*
H6B	0.4463	0.2766	0.0744	0.103*
H6C	0.3887	0.2581	0.1817	0.103*
C7	0.5043 (5)	0.4240 (5)	0.4975 (16)	0.068 (3)
H7A	0.4743	0.4483	0.4364	0.102*
H7B	0.5476	0.4426	0.4894	0.102*
H7C	0.4899	0.4262	0.5983	0.102*
C8	0.6086 (5)	0.1450 (4)	0.5793 (11)	0.049 (2)
H8A	0.6530	0.1401	0.6176	0.059*
H8B	0.6077	0.1268	0.4805	0.059*
C9	0.5614 (6)	0.1078 (5)	0.6754 (12)	0.060 (3)
H9	0.5739	0.0611	0.6762	0.072*
C10	0.4622 (13)	0.1031 (15)	0.7592 (18)	0.068 (8)	0.46 (4)
H10A	0.4659	0.0580	0.7939	0.081*	0.46 (4)
H10B	0.4160	0.1147	0.7488	0.081*	0.46 (4)
C11	0.4989 (6)	0.1514 (14)	0.859 (3)	0.068 (8)	0.46 (4)
H11A	0.4895	0.1969	0.8345	0.081*	0.46 (4)
H11B	0.4901	0.1436	0.9627	0.081*	0.46 (4)
C10'	0.4559 (11)	0.1331 (16)	0.7455 (19)	0.094 (10)	0.54 (4)
H10C	0.4157	0.1072	0.7479	0.113*	0.54 (4)
H10D	0.4448	0.1795	0.7401	0.113*	0.54 (4)
C11'	0.4999 (7)	0.1183 (18)	0.878 (3)	0.094 (10)	0.54 (4)
H11C	0.4898	0.1469	0.9609	0.113*	0.54 (4)
H11D	0.4960	0.0727	0.9091	0.113*	0.54 (4)
C12	0.2815 (5)	0.0217 (4)	−0.1225 (11)	0.043 (2)
C13	0.1621 (4)	0.0531 (4)	−0.1418 (12)	0.044 (2)
C14	0.1953 (4)	−0.0211 (3)	0.0451 (10)	0.0309 (19)
C15	0.2591 (4)	−0.0156 (4)	0.0084 (10)	0.035 (2)
C16	0.2515 (5)	−0.0846 (4)	0.1871 (11)	0.042 (2)
H16	0.2622	−0.1153	0.2593	0.050*
C17	0.2421 (6)	0.1030 (6)	−0.3009 (13)	0.080 (4)
H17A	0.2887	0.1019	−0.3196	0.119*
H17B	0.2294	0.1468	−0.2731	0.119*
H17C	0.2188	0.0902	−0.3885	0.119*
C18	0.0772 (5)	0.0074 (6)	0.0225 (16)	0.071 (4)
H18A	0.0507	0.0353	−0.0389	0.107*
H18B	0.0726	0.0207	0.1235	0.107*
H18C	0.0629	−0.0375	0.0119	0.107*
C19	0.3647 (4)	−0.0690 (5)	0.1035 (11)	0.045 (2)
H19A	0.3825	−0.0610	0.0058	0.054*
H19B	0.3736	−0.1145	0.1292	0.054*
C20	0.3981 (4)	−0.0246 (5)	0.2117 (13)	0.054 (3)
H20	0.4453	−0.0347	0.2153	0.065*
C22	0.367 (2)	0.0769 (14)	0.303 (2)	0.065 (11)	0.36 (4)
H22A	0.3207	0.0863	0.2988	0.078*	0.36 (4)
H22B	0.3915	0.1179	0.3141	0.078*	0.36 (4)
C21	0.383 (3)	0.0292 (8)	0.429 (3)	0.065 (11)	0.36 (4)
H21A	0.4289	0.0327	0.4606	0.078*	0.36 (4)
H21B	0.3543	0.0353	0.5127	0.078*	0.36 (4)
C22'	0.3901 (12)	0.0742 (11)	0.3145 (17)	0.078 (7)	0.64 (4)
H22C	0.3718	0.1183	0.3076	0.094*	0.64 (4)
H22D	0.4346	0.0769	0.3530	0.094*	0.64 (4)
C21'	0.3470 (14)	0.0299 (6)	0.411 (3)	0.078 (7)	0.64 (4)
H21C	0.3566	0.0348	0.5150	0.094*	0.64 (4)
H21D	0.3004	0.0365	0.3931	0.094*	0.64 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0695 (10)	0.0601 (10)	0.0411 (9)	−0.0070 (8)	0.0035 (8)	0.0009 (8)
Fe2	0.0745 (11)	0.0581 (10)	0.0432 (9)	0.0120 (8)	0.0031 (8)	0.0023 (8)
Cl1	0.105 (2)	0.078 (2)	0.078 (2)	0.0085 (18)	0.021 (2)	0.0265 (19)
Cl2	0.089 (2)	0.126 (3)	0.055 (2)	−0.026 (2)	−0.0054 (17)	−0.0144 (19)
Cl3	0.083 (2)	0.096 (2)	0.095 (3)	−0.0082 (18)	0.027 (2)	0.032 (2)
Cl4	0.128 (3)	0.082 (2)	0.064 (2)	0.003 (2)	−0.008 (2)	−0.0211 (18)
Cl5	0.087 (2)	0.0716 (18)	0.0619 (19)	−0.0058 (16)	0.0210 (17)	−0.0146 (15)
Cl6	0.136 (3)	0.0681 (19)	0.061 (2)	0.0021 (19)	−0.004 (2)	0.0153 (16)
Cl7	0.101 (3)	0.108 (3)	0.081 (2)	0.023 (2)	−0.027 (2)	0.010 (2)
Cl8	0.102 (3)	0.129 (3)	0.073 (2)	0.011 (2)	0.027 (2)	−0.018 (2)
O1	0.090 (5)	0.040 (4)	0.047 (4)	−0.004 (3)	−0.018 (4)	−0.019 (3)
O2	0.045 (4)	0.064 (4)	0.079 (6)	0.019 (3)	−0.012 (4)	0.022 (4)
O3	0.093 (6)	0.087 (6)	0.078 (7)	−0.033 (5)	−0.019 (5)	0.002 (5)
O4	0.086 (5)	0.093 (6)	0.036 (4)	0.012 (4)	−0.006 (4)	0.013 (4)
O5	0.035 (4)	0.097 (5)	0.044 (4)	−0.002 (3)	0.015 (3)	0.027 (4)
O6	0.065 (5)	0.068 (5)	0.071 (6)	0.020 (4)	−0.016 (4)	0.017 (4)
O7	0.098 (6)	0.055 (4)	0.034 (4)	−0.003 (4)	−0.015 (4)	0.011 (3)
O8	0.081 (5)	0.066 (5)	0.073 (6)	−0.024 (4)	0.002 (5)	0.009 (4)
N1	0.049 (4)	0.055 (5)	0.031 (4)	−0.003 (4)	−0.008 (4)	0.005 (4)
N2	0.050 (5)	0.024 (4)	0.056 (6)	0.008 (3)	−0.005 (4)	0.010 (3)
N3	0.048 (4)	0.041 (4)	0.022 (4)	0.009 (3)	−0.005 (3)	0.004 (3)
N4	0.061 (5)	0.036 (4)	0.038 (5)	0.003 (3)	−0.021 (4)	−0.014 (3)
N5	0.061 (5)	0.047 (4)	0.032 (4)	0.010 (4)	−0.010 (4)	0.009 (4)
N6	0.035 (4)	0.050 (5)	0.056 (5)	0.005 (3)	0.005 (4)	0.015 (4)
N7	0.037 (4)	0.039 (4)	0.027 (4)	0.003 (3)	0.002 (3)	0.012 (3)
N8	0.040 (4)	0.046 (4)	0.049 (5)	−0.010 (3)	0.013 (4)	0.000 (4)
C1	0.033 (5)	0.047 (5)	0.040 (6)	−0.003 (4)	0.004 (4)	0.010 (5)
C2	0.033 (5)	0.060 (6)	0.044 (6)	0.005 (4)	−0.009 (4)	0.014 (5)
C3	0.047 (5)	0.015 (4)	0.033 (5)	−0.012 (3)	0.009 (4)	−0.004 (3)
C4	0.038 (5)	0.052 (6)	0.026 (5)	−0.007 (4)	0.002 (4)	0.007 (4)
C5	0.052 (5)	0.035 (5)	0.033 (5)	0.004 (4)	−0.022 (4)	0.004 (4)
C6	0.088 (8)	0.071 (7)	0.046 (7)	0.008 (6)	−0.020 (6)	−0.001 (6)
C7	0.060 (7)	0.044 (6)	0.101 (10)	0.008 (5)	−0.027 (7)	0.001 (6)
C8	0.065 (6)	0.052 (6)	0.030 (5)	0.018 (5)	−0.010 (5)	0.003 (4)
C9	0.096 (9)	0.045 (6)	0.039 (6)	0.006 (5)	−0.021 (6)	0.010 (5)
C10	0.057 (13)	0.060 (14)	0.085 (17)	0.011 (9)	−0.009 (10)	0.043 (12)
C11	0.057 (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)
C12	0.053 (6)	0.035 (5)	0.041 (6)	−0.004 (4)	−0.007 (5)	0.005 (4)
C13	0.026 (4)	0.046 (5)	0.060 (7)	0.017 (4)	−0.014 (5)	−0.009 (5)
C14	0.037 (5)	0.019 (4)	0.037 (5)	−0.008 (3)	0.006 (4)	0.007 (3)
C15	0.048 (5)	0.025 (4)	0.032 (5)	0.003 (4)	0.002 (4)	0.002 (4)
C16	0.061 (6)	0.021 (4)	0.043 (6)	0.007 (4)	−0.008 (5)	0.018 (4)
C17	0.096 (9)	0.094 (9)	0.049 (8)	0.012 (7)	0.012 (7)	0.020 (7)
C18	0.038 (6)	0.072 (7)	0.103 (10)	0.003 (5)	0.003 (6)	0.015 (7)
C19	0.035 (5)	0.057 (6)	0.042 (6)	0.019 (4)	−0.008 (4)	0.007 (5)
C20	0.034 (5)	0.059 (6)	0.069 (8)	0.011 (4)	0.003 (5)	0.015 (6)
C22	0.06 (2)	0.051 (16)	0.08 (2)	−0.008 (12)	0.016 (14)	0.002 (14)
C21	0.06 (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, º) top

Fe1—Cl1	2.173 (3)	N8—H8	0.8600
Fe1—Cl3	2.173 (3)	C1—C4	1.446 (13)
Fe1—Cl2	2.183 (4)	C3—C4	1.357 (12)
Fe1—Cl4	2.190 (4)	C5—H5	0.9300
Fe2—Cl8	2.165 (4)	C6—H6A	0.9600
Fe2—Cl6	2.183 (3)	C6—H6B	0.9600
Fe2—Cl5	2.185 (3)	C6—H6C	0.9600
Fe2—Cl7	2.189 (4)	C7—H7A	0.9600
O1—C1	1.189 (10)	C7—H7B	0.9600
O2—C2	1.206 (11)	C7—H7C	0.9600
O3—C9	1.368 (13)	C8—C9	1.499 (14)
O3—C10	1.441 (10)	C8—H8A	0.9700
O3—C10'	1.450 (10)	C8—H8B	0.9700
O4—C9	1.383 (13)	C9—H9	0.9800
O4—C11	1.442 (10)	C10—C11	1.528 (10)
O4—C11'	1.454 (10)	C10—H10A	0.9700
O5—C12	1.173 (10)	C10—H10B	0.9700
O6—C13	1.201 (10)	C11—H11A	0.9700
O7—C20	1.398 (13)	C11—H11B	0.9700
O7—C21'	1.444 (9)	C10'—C11'	1.529 (10)
O7—C21	1.447 (10)	C10'—H10C	0.9700
O8—C20	1.396 (12)	C10'—H10D	0.9700
O8—C22'	1.443 (10)	C11'—H11C	0.9700
O8—C22	1.446 (10)	C11'—H11D	0.9700
N1—C2	1.386 (12)	C12—C15	1.479 (12)
N1—C1	1.417 (11)	C14—C15	1.342 (11)
N1—C6	1.467 (13)	C16—H16	0.9300
N2—C3	1.349 (11)	C17—H17A	0.9600
N2—C2	1.382 (12)	C17—H17B	0.9600
N2—C7	1.473 (12)	C17—H17C	0.9600
N3—C5	1.302 (11)	C18—H18A	0.9600
N3—C4	1.384 (11)	C18—H18B	0.9600
N3—C8	1.477 (11)	C18—H18C	0.9600
N4—C5	1.316 (10)	C19—C20	1.494 (14)
N4—C3	1.372 (11)	C19—H19A	0.9700
N4—H4	0.8600	C19—H19B	0.9700
N5—C13	1.344 (11)	C20—H20	0.9800
N5—C12	1.427 (11)	C22—C21	1.530 (10)
N5—C17	1.486 (13)	C22—H22A	0.9700
N6—C14	1.346 (11)	C22—H22B	0.9700
N6—C13	1.394 (13)	C21—H21A	0.9700
N6—C18	1.473 (12)	C21—H21B	0.9700
N7—C16	1.274 (11)	C22'—C21'	1.528 (10)
N7—C15	1.399 (10)	C22'—H22C	0.9700
N7—C19	1.456 (10)	C22'—H22D	0.9700
N8—C16	1.335 (11)	C21'—H21C	0.9700
N8—C14	1.365 (11)	C21'—H21D	0.9700

Cl1—Fe1—Cl3	111.77 (15)	O3—C10—C11	99.2 (16)
Cl1—Fe1—Cl2	109.10 (16)	O3—C10—H10A	111.9
Cl3—Fe1—Cl2	110.66 (17)	C11—C10—H10A	111.9
Cl1—Fe1—Cl4	109.65 (16)	O3—C10—H10B	111.9
Cl3—Fe1—Cl4	108.16 (16)	C11—C10—H10B	111.9
Cl2—Fe1—Cl4	107.41 (16)	H10A—C10—H10B	109.6
Cl8—Fe2—Cl6	109.43 (17)	O4—C11—C10	97.2 (16)
Cl8—Fe2—Cl5	109.77 (15)	O4—C11—H11A	112.3
Cl6—Fe2—Cl5	109.54 (15)	C10—C11—H11A	112.3
Cl8—Fe2—Cl7	110.21 (18)	O4—C11—H11B	112.3
Cl6—Fe2—Cl7	109.58 (17)	C10—C11—H11B	112.3
Cl5—Fe2—Cl7	108.28 (15)	H11A—C11—H11B	109.9
C9—O3—C10	100.2 (14)	O3—C10'—C11'	101.4 (17)
C9—O3—C10'	108.8 (12)	O3—C10'—H10C	111.5
C10—O3—C10'	25.3 (10)	C11'—C10'—H10C	111.5
C9—O4—C11	107.1 (13)	O3—C10'—H10D	111.5
C9—O4—C11'	103.8 (15)	C11'—C10'—H10D	111.5
C11—O4—C11'	27.7 (10)	H10C—C10'—H10D	109.3
C20—O7—C21'	112.1 (10)	O4—C11'—C10'	101.1 (15)
C20—O7—C21	106.0 (16)	O4—C11'—H11C	111.6
C21'—O7—C21	30.3 (14)	C10'—C11'—H11C	111.6
C20—O8—C22'	102.7 (12)	O4—C11'—H11D	111.6
C20—O8—C22	108.4 (14)	C10'—C11'—H11D	111.6
C22'—O8—C22	18.9 (19)	H11C—C11'—H11D	109.4
C2—N1—C1	128.4 (8)	O5—C12—N5	125.8 (9)
C2—N1—C6	115.5 (8)	O5—C12—C15	126.6 (8)
C1—N1—C6	116.1 (8)	N5—C12—C15	107.5 (8)
C3—N2—C2	119.4 (7)	O6—C13—N5	123.8 (10)
C3—N2—C7	121.2 (8)	O6—C13—N6	119.9 (8)
C2—N2—C7	119.3 (8)	N5—C13—N6	116.3 (7)
C5—N3—C4	107.5 (7)	C15—C14—N6	123.4 (7)
C5—N3—C8	125.4 (7)	C15—C14—N8	108.4 (7)
C4—N3—C8	126.9 (7)	N6—C14—N8	128.2 (7)
C5—N4—C3	107.2 (7)	C14—C15—N7	106.5 (7)
C5—N4—H4	126.4	C14—C15—C12	122.6 (8)
C3—N4—H4	126.4	N7—C15—C12	130.2 (8)
C13—N5—C12	130.1 (8)	N7—C16—N8	112.6 (8)
C13—N5—C17	115.8 (8)	N7—C16—H16	123.7
C12—N5—C17	114.1 (8)	N8—C16—H16	123.7
C14—N6—C13	119.3 (7)	N5—C17—H17A	109.5
C14—N6—C18	122.5 (8)	N5—C17—H17B	109.5
C13—N6—C18	118.1 (8)	H17A—C17—H17B	109.5
C16—N7—C15	106.8 (7)	N5—C17—H17C	109.5
C16—N7—C19	126.5 (7)	H17A—C17—H17C	109.5
C15—N7—C19	126.7 (7)	H17B—C17—H17C	109.5
C16—N8—C14	105.6 (7)	N6—C18—H18A	109.5
C16—N8—H8	127.2	N6—C18—H18B	109.5
C14—N8—H8	127.2	H18A—C18—H18B	109.5
O1—C1—N1	122.0 (9)	N6—C18—H18C	109.5
O1—C1—C4	128.4 (9)	H18A—C18—H18C	109.5
N1—C1—C4	109.5 (8)	H18B—C18—H18C	109.5
O2—C2—N2	120.6 (9)	N7—C19—C20	111.3 (8)
O2—C2—N1	123.2 (9)	N7—C19—H19A	109.4
N2—C2—N1	116.2 (8)	C20—C19—H19A	109.4
N2—C3—C4	123.5 (8)	N7—C19—H19B	109.4
N2—C3—N4	129.1 (7)	C20—C19—H19B	109.4
C4—C3—N4	107.4 (7)	H19A—C19—H19B	108.0
C3—C4—N3	106.5 (8)	O8—C20—O7	105.9 (8)
C3—C4—C1	122.3 (8)	O8—C20—C19	110.7 (9)
N3—C4—C1	130.6 (8)	O7—C20—C19	110.6 (8)
N3—C5—N4	111.3 (8)	O8—C20—H20	109.8
N3—C5—H5	124.3	O7—C20—H20	109.8
N4—C5—H5	124.3	C19—C20—H20	109.8
N1—C6—H6A	109.5	O8—C22—C21	103.2 (18)
N1—C6—H6B	109.5	O8—C22—H22A	111.1
H6A—C6—H6B	109.5	C21—C22—H22A	111.1
N1—C6—H6C	109.5	O8—C22—H22B	111.1
H6A—C6—H6C	109.5	C21—C22—H22B	111.1
H6B—C6—H6C	109.5	H22A—C22—H22B	109.1
N2—C7—H7A	109.5	O7—C21—C22	98.3 (18)
N2—C7—H7B	109.5	O7—C21—H21A	112.1
H7A—C7—H7B	109.5	C22—C21—H21A	112.1
N2—C7—H7C	109.5	O7—C21—H21B	112.1
H7A—C7—H7C	109.5	C22—C21—H21B	112.1
H7B—C7—H7C	109.5	H21A—C21—H21B	109.7
N3—C8—C9	110.9 (8)	O8—C22'—C21'	103.0 (13)
N3—C8—H8A	109.5	O8—C22'—H22C	111.2
C9—C8—H8A	109.5	C21'—C22'—H22C	111.2
N3—C8—H8B	109.5	O8—C22'—H22D	111.2
C9—C8—H8B	109.5	C21'—C22'—H22D	111.2
H8A—C8—H8B	108.0	H22C—C22'—H22D	109.1
O3—C9—O4	109.3 (10)	O7—C21'—C22'	96.4 (14)
O3—C9—C8	111.1 (8)	O7—C21'—H21C	112.5
O4—C9—C8	109.3 (9)	C22'—C21'—H21C	112.5
O3—C9—H9	109.0	O7—C21'—H21D	112.5
O4—C9—H9	109.0	C22'—C21'—H21D	112.5
C8—C9—H9	109.0	H21C—C21'—H21D	110.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2ⁱ	0.86	1.93	2.774 (9)	165
N8—H8···O6ⁱⁱ	0.86	1.91	2.754 (9)	166
C5—H5···Cl5ⁱ	0.93	2.80	3.650 (11)	153
C8—H8B···O7ⁱⁱⁱ	0.97	2.29	3.114 (11)	142
C10—H10C···O5^iv	0.95	2.46	3.098 (11)	124
C10′—H10B···O5^iv	0.89	2.57	3.384 (11)	153
C10′—H10C···O5^iv	0.97	2.46	3.384 (11)	159
C16—H16···Cl1ⁱⁱⁱ	0.93	2.78	3.560 (11)	143
C19—H19A···O4^v	0.97	2.48	3.227 (11)	134
C19—H19A···O5	0.97	2.53	3.167 (11)	123
C22′—H22D···O1	0.97	2.58	3.242 (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.

Experimental details

Crystal data
Chemical formula	(C₁₁H₁₅N₄O₄)[FeCl₄]
M_r	464.92
Crystal system, space group	Tetragonal, P4₂
Temperature (K)	293
a, c (Å)	20.2947 (4), 9.0692 (4)
V (Å³)	3735.38 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.40
Crystal size (mm)	0.27 × 0.16 × 0.13

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.775, 0.852
No. of measured, independent and observed [I > 2σ(I)] reflections	19874, 6253, 5589
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.099, 0.207, 1.30
No. of reflections	6253
No. of parameters	447
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.31
Absolute structure	Flack (1983), 2724 Friedel pairs
Absolute structure parameter	0.10 (4)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2ⁱ	0.86	1.93	2.774 (9)	165.1
N8—H8···O6ⁱⁱ	0.86	1.91	2.754 (9)	166.4
C5—H5···Cl5ⁱ	0.93	2.80	3.650 (11)	152.8
C8—H8B···O7ⁱⁱⁱ	0.97	2.29	3.114 (11)	141.8
C10—H10C···O5^iv	0.95	2.46	3.098 (11)	124.2
C10'—H10B···O5^iv	0.89	2.57	3.384 (11)	152.5
C10'—H10C···O5^iv	0.97	2.46	3.384 (11)	158.9
C16—H16···Cl1ⁱⁱⁱ	0.93	2.78	3.560 (11)	142.8
C19—H19A···O4^v	0.97	2.48	3.227 (11)	133.8
C19—H19A···O5	0.97	2.53	3.167 (11)	123.0
C22'—H22D···O1	0.97	2.58	3.242 (11)	126.1

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.

Acknowledgements

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).

References

Barbaro, P., Bianchini, C., Fochi, M., Masi, D. & Mealli, C. (1992). Acta Cryst. C48, 625–627. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Bottomley, G. A., Carter, A. M., Engelhardt, L. M., Lincoln, F. J. & Patric, J. M. (1984). Aust. J. Chem. 37, 871–877. CSD CrossRef CAS Web of Science Google Scholar
Bruker (2000). SMART, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Franzone, J. S., Cirillo, R. & Biffignandi, P. (1989). Eur. J. Pharmacol. 165, 269–274. CrossRef CAS PubMed Web of Science Google Scholar
Franzone, J. S., Reboani, C. & Fonzo, D. (1981). Farmacol. Sci. 36, 201–219. CAS Google Scholar
Li, C. H., Luo, Z. & Li, Z. H. (1995). Chin. J. Pharm. 25, 385–386. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, J. J. & Li, L. (2001). J. Norman Bethune Univ. Med. Sci. 27, 646–676. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1247

doi:10.1107/S1600536810034720

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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