metal-organic compounds
Poly[tris{μ-2-[(dimethylamino)methyl]imidazolato-κ3N1,N2:N3}(nitrato-κO)dizinc(II)]
aDepartment of Chemistry, Faculty of Science, Kyushu University, Moto-oka 744, Nishi-ku, Fukuoka 819-0395, Japan, and bInternational Institute for Carbon-Neutral Energy Research (WPI-I2CNER), Kyushu University, Moto-oka 744, Nishi-ku, Fukuoka 819-0395, Japan
*Correspondence e-mail: sadakiyo@i2cner.kyushu-u.ac.jp
In the title coordination polymer, [Zn2(C6H10N3)3(NO3)]n, two independent ZnII ions are tetrahedrally coordinated by the anionic ligands, viz. 2-[(dimethylamino)methyl]imidazolate or nitrate ions. One ZnII ion is coordinated by the imidazolate N atoms of three anions and an O atom of the nitrate ion. The second ZnII ion is coordinated by imidazolate N atoms of three anions and one amino N atom of one such ligand. The 2-[(dimethylamino)methyl]imidazolate anions are bridging the ZnII ions to form a helical chain structure along [001]. The chains are further linked by the bridging ligands into a three-dimensional framework structure. The nitrate anion is disordered over two sets of sites and was refined with two pairs of three O atoms using half-occupancy for each O atom.
Keywords: crystal structure; zinc; coordination polymer; imidazolate.
CCDC reference: 1509625
Structure description
Metal–organic compounds with framework structures and in particular coordination polymers containing imidazolate linkers have been widely studied to create various zeolite-like compounds (Park et al., 2006) because the bridging angle of the imidazolate ligands (145°) is close to that of Si—O—Si in zeolites. In the present study, the structure of a new imidazolate-bridged coordination polymer, [Zn2(C6H10N3)3(NO3)]n, is reported.
In the II ions. Since the 2-[(dimethylamino)methyl]imidazolate ligand also has an amino group as an additional coordination site, Zn2 is tetrahedrally coordinated by three imidazolate N atoms and one amino N atom, and thus Zn2 is bridged to three adjacent Zn1 ions. Zn1, on the other hand, is tetrahedrally coordinated by three imidazolate N atoms and one nitrate O atom, whereby the nitrate anion is positionally disordered over two sites (Fig. 1). The Zn1 and Zn2 ions construct helical chains along [001] (Fig. 2). These chains are further connected to neighboring chains through the imidazolato ligands to build up a three-dimensional framework structure (Fig. 3).
three unique 2-[(dimethylamino)methyl]imidazolate ligands bridge two unique ZnSynthesis and crystallization
For the preparation of 2-[(dimethylamino)methyl]imidazole, see: Quan et al. (2005).
A mixture of imidazole-2-carbaldehyde (9.609 g, 100 mmol) in methanol (100 ml) was put in a 500 ml two-neck round-bottomed flask equipped with a reflux condenser. To this suspension, a solution of dimethylamine (40% aqueous solution, 100 ml) was slowly added at room temperature. After that, sodium borohydride (11.349 g, 300 mmol) was cautiously added portionwise over 45 min. The reaction mixture was then refluxed for two days. The reaction contents were concentrated by evaporation and added to a 500 ml separatory funnel containing brine (200 ml). The contents were extracted with ethyl acetate (2 × 200 ml) and the ethyl acetate extract was discarded. The aqueous layer was extracted with CHCl3 (4 × 150 ml) and the organic layer dried over Na2SO4, filtered, and concentrated under vacuum to give 2-[(dimethylamino)methyl]imidazole as a yellow solid. 1H NMR(D2O): δ = 7.07(s, 2H), 3.60(s, 2H), and 2.21(s, 6H) p.p.m.
Crystals of [Zn2(C6H10N3)3(NO3)]n were grown by pouring a solution of 2-[(dimethylamino)methyl]imidazole (0.520 g, 4.14 mmol) with methanol (5.0 ml) slowly onto a solution of Zn(NO3)2·6H2O (0.496 g, 1.67 mmol) in methanol (5.0 ml) in a test tube. After keeping the solution at 323 K for two days, colorless hexagonal-shaped single crystals were obtained.
Refinement
Crystal data, data collection and structure . The refined to 0.010 (8), indicating that the determination of the is correct. The nitrate anion is disordered over two sets of sites and was refined with two pairs of three O atoms using half-occupancy for each O atom.
details are summarized in Table 1Structural data
CCDC reference: 1509625
https://doi.org/10.1107/S2414314616016266/wm4025sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616016266/wm4025Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616016266/wm4025Isup3.cdx
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: Yadokari-XG (Kabuto et al., 2009).[Zn2(C6H10N3)3(NO3)] | Dx = 1.596 Mg m−3 |
Mr = 565.26 | Mo Kα radiation, λ = 0.71069 Å |
Hexagonal, P61 | Cell parameters from 9942 reflections |
Hall symbol: P 61 | θ = 2.5–28.8° |
a = 9.2437 (8) Å | µ = 2.08 mm−1 |
c = 47.683 (4) Å | T = 100 K |
V = 3528.5 (5) Å3 | Block, colorless |
Z = 6 | 0.10 × 0.10 × 0.10 mm |
F(000) = 1752 |
Bruker APEXII CCD diffractometer | 5835 independent reflections |
Radiation source: fine-focus sealed tube | 5595 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 29.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −9→12 |
Tmin = 0.819, Tmax = 0.819 | k = −11→12 |
21198 measured reflections | l = −64→64 |
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0286P)2 + 1.2071P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5835 reflections | Δρmax = 0.86 e Å−3 |
331 parameters | Δρmin = −0.26 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2004 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.010 (8) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.96338 (4) | 0.51358 (3) | 0.423976 (5) | 0.02299 (7) | |
Zn2 | 0.91659 (3) | 0.90826 (3) | 0.517388 (5) | 0.01875 (6) | |
N1 | 1.0431 (2) | 0.7009 (2) | 0.39668 (4) | 0.0187 (4) | |
N2 | 0.8514 (2) | 0.7160 (2) | 0.49260 (4) | 0.0189 (4) | |
N3 | 1.1380 (2) | 1.0233 (2) | 0.53585 (4) | 0.0191 (4) | |
N4 | 0.8770 (2) | 0.5671 (2) | 0.45813 (4) | 0.0188 (4) | |
N5 | 0.8621 (3) | 0.2810 (2) | 0.41073 (4) | 0.0227 (4) | |
N6 | 0.7489 (2) | 0.8132 (2) | 0.55003 (4) | 0.0204 (4) | |
N7 | 0.6872 (2) | 0.4885 (2) | 0.39504 (4) | 0.0213 (4) | |
C1 | 0.9489 (3) | 0.7127 (3) | 0.47207 (5) | 0.0172 (4) | |
N8 | 1.1186 (2) | 1.0145 (2) | 0.46746 (4) | 0.0215 (4) | |
N9 | 0.8060 (2) | 1.0574 (2) | 0.51150 (4) | 0.0214 (4) | |
C2 | 0.7078 (3) | 0.5625 (3) | 0.49164 (5) | 0.0220 (4) | |
H1 | 0.6137 | 0.5261 | 0.5036 | 0.026* | |
N10 | 1.2858 (3) | 0.5830 (3) | 0.44997 (5) | 0.0295 (5) | |
C3 | 0.9140 (3) | 0.2259 (3) | 0.38929 (5) | 0.0201 (4) | |
C4 | 1.2009 (3) | 0.8129 (3) | 0.38672 (5) | 0.0233 (5) | |
H2 | 1.3008 | 0.8116 | 0.3908 | 0.028* | |
C5 | 1.1198 (3) | 0.8562 (3) | 0.46715 (5) | 0.0192 (4) | |
H3 | 1.1962 | 0.8583 | 0.4819 | 0.023* | |
H4 | 1.1617 | 0.8426 | 0.4488 | 0.023* | |
C6 | 0.6743 (3) | 0.6850 (3) | 0.56929 (5) | 0.0238 (5) | |
H5 | 0.6916 | 0.5922 | 0.5708 | 0.029* | |
C7 | 0.7236 (3) | 0.4722 (3) | 0.47082 (5) | 0.0234 (5) | |
H6 | 0.6422 | 0.3615 | 0.4657 | 0.028* | |
C8 | 1.2627 (3) | 1.1880 (3) | 0.53668 (5) | 0.0237 (5) | |
H7 | 1.2616 | 1.2777 | 0.5272 | 0.028* | |
C9 | 0.9425 (3) | 0.7511 (3) | 0.38563 (5) | 0.0170 (4) | |
C10 | 0.6820 (3) | 0.4142 (3) | 0.36753 (5) | 0.0280 (5) | |
H8 | 0.6079 | 0.4310 | 0.3550 | 0.042* | |
H9 | 0.6400 | 0.2943 | 0.3698 | 0.042* | |
H10 | 0.7948 | 0.4677 | 0.3595 | 0.042* | |
C11 | 0.7485 (3) | 1.0731 (3) | 0.53982 (5) | 0.0235 (5) | |
H11 | 0.6570 | 1.0987 | 0.5380 | 0.028* | |
H12 | 0.8417 | 1.1662 | 0.5501 | 0.028* | |
C12 | 0.7593 (3) | 0.6679 (3) | 0.39220 (5) | 0.0198 (4) | |
H13 | 0.7430 | 0.7142 | 0.4099 | 0.024* | |
H14 | 0.7011 | 0.6917 | 0.3770 | 0.024* | |
C13 | 0.6598 (3) | 0.9608 (3) | 0.49275 (5) | 0.0292 (5) | |
H15 | 0.5967 | 1.0196 | 0.4910 | 0.044* | |
H16 | 0.5877 | 0.8496 | 0.5007 | 0.044* | |
H17 | 0.6989 | 0.9496 | 0.4742 | 0.044* | |
C14 | 1.0359 (3) | 1.0285 (3) | 0.44220 (5) | 0.0285 (5) | |
H18 | 1.0997 | 1.0314 | 0.4256 | 0.043* | |
H19 | 1.0301 | 1.1314 | 0.4431 | 0.043* | |
H20 | 0.9227 | 0.9321 | 0.4410 | 0.043* | |
C15 | 0.9136 (4) | 1.2257 (3) | 0.49959 (6) | 0.0308 (5) | |
H21 | 0.9518 | 1.2155 | 0.4809 | 0.046* | |
H22 | 1.0105 | 1.2891 | 0.5118 | 0.046* | |
H23 | 0.8499 | 1.2841 | 0.4981 | 0.046* | |
C16 | 0.7148 (3) | 0.1427 (3) | 0.41900 (5) | 0.0260 (5) | |
H24 | 0.6451 | 0.1404 | 0.4338 | 0.031* | |
C17 | 1.2918 (3) | 1.1527 (3) | 0.46788 (6) | 0.0322 (6) | |
H25 | 1.3490 | 1.1496 | 0.4508 | 0.048* | |
H26 | 1.3493 | 1.1417 | 0.4843 | 0.048* | |
H27 | 1.2927 | 1.2591 | 0.4688 | 0.048* | |
C18 | 0.5178 (3) | 0.4166 (4) | 0.40630 (6) | 0.0340 (6) | |
H28 | 0.5221 | 0.4640 | 0.4249 | 0.051* | |
H29 | 0.4678 | 0.2952 | 0.4079 | 0.051* | |
H30 | 0.4500 | 0.4424 | 0.3937 | 0.051* | |
O1 | 1.2289 (5) | 0.5962 (6) | 0.42732 (8) | 0.0351 (9) | 0.50 |
O2 | 1.1877 (7) | 0.4844 (8) | 0.46768 (10) | 0.0545 (13) | 0.50 |
O3 | 1.4340 (5) | 0.6432 (7) | 0.45486 (11) | 0.0483 (11) | 0.50 |
O4 | 1.3830 (9) | 0.7235 (7) | 0.44125 (15) | 0.092 (2) | 0.50 |
O5 | 1.1560 (6) | 0.4869 (6) | 0.43798 (13) | 0.0569 (14) | 0.50 |
O6 | 1.3130 (11) | 0.5543 (7) | 0.47393 (11) | 0.086 (2) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.03698 (15) | 0.02441 (13) | 0.01474 (11) | 0.02071 (12) | 0.00109 (11) | −0.00093 (10) |
Zn2 | 0.02086 (12) | 0.02111 (12) | 0.01535 (11) | 0.01129 (10) | −0.00115 (10) | −0.00447 (10) |
N1 | 0.0165 (8) | 0.0235 (9) | 0.0162 (9) | 0.0102 (7) | −0.0002 (7) | −0.0016 (7) |
N2 | 0.0209 (9) | 0.0191 (9) | 0.0143 (8) | 0.0081 (7) | 0.0009 (7) | −0.0018 (7) |
N3 | 0.0217 (9) | 0.0173 (8) | 0.0167 (9) | 0.0085 (7) | 0.0011 (7) | −0.0010 (7) |
N4 | 0.0225 (9) | 0.0179 (8) | 0.0151 (9) | 0.0095 (7) | −0.0004 (7) | −0.0016 (7) |
N5 | 0.0373 (11) | 0.0253 (10) | 0.0122 (9) | 0.0206 (9) | 0.0016 (8) | 0.0011 (7) |
N6 | 0.0213 (9) | 0.0212 (9) | 0.0170 (9) | 0.0093 (8) | 0.0006 (7) | −0.0003 (7) |
N7 | 0.0167 (9) | 0.0220 (9) | 0.0206 (9) | 0.0063 (7) | −0.0016 (7) | 0.0009 (8) |
C1 | 0.0226 (10) | 0.0197 (9) | 0.0114 (9) | 0.0122 (8) | −0.0005 (8) | −0.0003 (7) |
N8 | 0.0263 (10) | 0.0178 (8) | 0.0156 (9) | 0.0074 (7) | −0.0008 (7) | −0.0011 (7) |
N9 | 0.0264 (9) | 0.0254 (9) | 0.0150 (9) | 0.0149 (8) | 0.0030 (7) | −0.0003 (7) |
C2 | 0.0203 (10) | 0.0197 (10) | 0.0215 (11) | 0.0067 (9) | 0.0060 (9) | 0.0007 (9) |
N10 | 0.0276 (11) | 0.0275 (10) | 0.0348 (13) | 0.0148 (9) | −0.0076 (9) | −0.0033 (9) |
C3 | 0.0261 (11) | 0.0236 (11) | 0.0142 (10) | 0.0151 (9) | −0.0047 (8) | −0.0041 (8) |
C4 | 0.0164 (10) | 0.0322 (12) | 0.0213 (11) | 0.0121 (9) | −0.0007 (9) | −0.0020 (9) |
C5 | 0.0224 (10) | 0.0230 (10) | 0.0135 (10) | 0.0124 (9) | 0.0014 (8) | −0.0020 (8) |
C6 | 0.0207 (10) | 0.0254 (11) | 0.0220 (11) | 0.0091 (9) | −0.0002 (9) | 0.0035 (9) |
C7 | 0.0247 (11) | 0.0180 (10) | 0.0232 (12) | 0.0074 (9) | −0.0009 (9) | −0.0034 (9) |
C8 | 0.0289 (12) | 0.0174 (10) | 0.0224 (12) | 0.0097 (9) | 0.0035 (9) | 0.0027 (9) |
C9 | 0.0164 (9) | 0.0191 (9) | 0.0151 (10) | 0.0087 (8) | −0.0019 (8) | −0.0042 (8) |
C10 | 0.0284 (12) | 0.0265 (12) | 0.0217 (12) | 0.0082 (10) | −0.0052 (10) | −0.0029 (9) |
C11 | 0.0301 (12) | 0.0281 (11) | 0.0164 (11) | 0.0177 (10) | 0.0054 (9) | −0.0011 (9) |
C12 | 0.0169 (10) | 0.0237 (11) | 0.0198 (11) | 0.0109 (8) | −0.0003 (8) | 0.0010 (9) |
C13 | 0.0307 (12) | 0.0433 (14) | 0.0183 (11) | 0.0221 (11) | −0.0015 (10) | 0.0029 (10) |
C14 | 0.0416 (14) | 0.0278 (12) | 0.0172 (11) | 0.0181 (11) | −0.0037 (10) | 0.0023 (9) |
C15 | 0.0392 (14) | 0.0317 (13) | 0.0265 (13) | 0.0216 (11) | 0.0098 (11) | 0.0072 (10) |
C16 | 0.0379 (13) | 0.0328 (12) | 0.0171 (11) | 0.0252 (11) | 0.0046 (9) | 0.0050 (9) |
C17 | 0.0306 (13) | 0.0243 (12) | 0.0254 (13) | 0.0014 (10) | 0.0080 (10) | 0.0022 (10) |
C18 | 0.0194 (11) | 0.0378 (14) | 0.0333 (15) | 0.0055 (10) | 0.0016 (10) | 0.0053 (11) |
O1 | 0.034 (2) | 0.055 (3) | 0.0236 (19) | 0.027 (2) | −0.0030 (15) | 0.0123 (18) |
O2 | 0.049 (3) | 0.084 (4) | 0.028 (2) | 0.033 (3) | 0.010 (2) | 0.026 (2) |
O3 | 0.0231 (19) | 0.068 (3) | 0.056 (3) | 0.025 (2) | −0.0217 (19) | −0.017 (2) |
O4 | 0.091 (5) | 0.045 (3) | 0.072 (4) | −0.017 (3) | −0.008 (4) | 0.028 (3) |
O5 | 0.032 (2) | 0.045 (3) | 0.090 (4) | 0.017 (2) | −0.024 (3) | −0.015 (3) |
O6 | 0.128 (6) | 0.051 (3) | 0.031 (3) | 0.008 (4) | −0.028 (4) | −0.004 (2) |
Zn1—N5 | 1.971 (2) | C4—H2 | 0.9500 |
Zn1—N4 | 1.9827 (19) | C5—H3 | 0.9900 |
Zn1—N1 | 1.9898 (19) | C5—H4 | 0.9900 |
Zn1—O5 | 2.029 (4) | C6—C16ii | 1.357 (3) |
Zn1—O1 | 2.182 (4) | C6—H5 | 0.9500 |
Zn2—N2 | 1.9611 (19) | C7—H6 | 0.9500 |
Zn2—N3 | 1.979 (2) | C8—C4i | 1.361 (4) |
Zn2—N6 | 2.058 (2) | C8—H7 | 0.9500 |
Zn2—N9 | 2.1054 (19) | C9—N3iv | 1.336 (3) |
N1—C9 | 1.338 (3) | C9—C12 | 1.502 (3) |
N1—C4 | 1.383 (3) | C10—H8 | 0.9800 |
N2—C1 | 1.341 (3) | C10—H9 | 0.9800 |
N2—C2 | 1.376 (3) | C10—H10 | 0.9800 |
N3—C9i | 1.336 (3) | C11—C3ii | 1.499 (3) |
N3—C8 | 1.376 (3) | C11—H11 | 0.9900 |
N4—C1 | 1.342 (3) | C11—H12 | 0.9900 |
N4—C7 | 1.379 (3) | C12—H13 | 0.9900 |
N5—C3 | 1.333 (3) | C12—H14 | 0.9900 |
N5—C16 | 1.379 (3) | C13—H15 | 0.9800 |
N6—C3ii | 1.337 (3) | C13—H16 | 0.9800 |
N6—C6 | 1.381 (3) | C13—H17 | 0.9800 |
N7—C12 | 1.451 (3) | C14—H18 | 0.9800 |
N7—C18 | 1.463 (3) | C14—H19 | 0.9800 |
N7—C10 | 1.470 (3) | C14—H20 | 0.9800 |
C1—C5 | 1.489 (3) | C15—H21 | 0.9800 |
N8—C17 | 1.466 (3) | C15—H22 | 0.9800 |
N8—C14 | 1.466 (3) | C15—H23 | 0.9800 |
N8—C5 | 1.468 (3) | C16—C6iii | 1.357 (3) |
N9—C15 | 1.479 (3) | C16—H24 | 0.9500 |
N9—C11 | 1.484 (3) | C17—H25 | 0.9800 |
N9—C13 | 1.489 (3) | C17—H26 | 0.9800 |
C2—C7 | 1.351 (3) | C17—H27 | 0.9800 |
C2—H1 | 0.9500 | C18—H28 | 0.9800 |
N10—O3 | 1.216 (4) | C18—H29 | 0.9800 |
N10—O5 | 1.220 (5) | C18—H30 | 0.9800 |
N10—O4 | 1.225 (5) | O1—O5 | 1.026 (6) |
N10—O6 | 1.227 (6) | O1—O4 | 1.476 (8) |
N10—O1 | 1.234 (4) | O2—O6 | 1.049 (9) |
N10—O2 | 1.240 (5) | O2—O5 | 1.448 (8) |
C3—N6iii | 1.337 (3) | O3—O4 | 1.243 (9) |
C3—C11iii | 1.499 (3) | O3—O6 | 1.354 (9) |
C4—C8iv | 1.361 (4) | ||
N5—Zn1—N4 | 120.32 (8) | C2—C7—H6 | 125.6 |
N5—Zn1—N1 | 120.45 (8) | N4—C7—H6 | 125.6 |
N4—Zn1—N1 | 109.89 (8) | C4i—C8—N3 | 108.6 (2) |
N5—Zn1—O5 | 86.57 (15) | C4i—C8—H7 | 125.7 |
N4—Zn1—O5 | 104.32 (19) | N3—C8—H7 | 125.7 |
N1—Zn1—O5 | 110.81 (19) | N3iv—C9—N1 | 112.97 (19) |
N5—Zn1—O1 | 104.05 (14) | N3iv—C9—C12 | 124.2 (2) |
N4—Zn1—O1 | 112.07 (12) | N1—C9—C12 | 122.8 (2) |
N1—Zn1—O1 | 83.14 (12) | N7—C10—H8 | 109.5 |
O5—Zn1—O1 | 27.90 (18) | N7—C10—H9 | 109.5 |
N2—Zn2—N3 | 121.43 (8) | H8—C10—H9 | 109.5 |
N2—Zn2—N6 | 104.15 (8) | N7—C10—H10 | 109.5 |
N3—Zn2—N6 | 104.40 (8) | H8—C10—H10 | 109.5 |
N2—Zn2—N9 | 118.88 (8) | H9—C10—H10 | 109.5 |
N3—Zn2—N9 | 114.69 (8) | N9—C11—C3ii | 110.31 (18) |
N6—Zn2—N9 | 82.62 (8) | N9—C11—H11 | 109.6 |
C9—N1—C4 | 105.11 (19) | C3ii—C11—H11 | 109.6 |
C9—N1—Zn1 | 122.68 (15) | N9—C11—H12 | 109.6 |
C4—N1—Zn1 | 132.00 (16) | C3ii—C11—H12 | 109.6 |
C1—N2—C2 | 105.33 (19) | H11—C11—H12 | 108.1 |
C1—N2—Zn2 | 123.71 (15) | N7—C12—C9 | 111.15 (18) |
C2—N2—Zn2 | 130.96 (15) | N7—C12—H13 | 109.4 |
C9i—N3—C8 | 105.18 (19) | C9—C12—H13 | 109.4 |
C9i—N3—Zn2 | 122.17 (15) | N7—C12—H14 | 109.4 |
C8—N3—Zn2 | 132.59 (16) | C9—C12—H14 | 109.4 |
C1—N4—C7 | 104.87 (18) | H13—C12—H14 | 108.0 |
C1—N4—Zn1 | 126.74 (15) | N9—C13—H15 | 109.5 |
C7—N4—Zn1 | 128.02 (15) | N9—C13—H16 | 109.5 |
C3—N5—C16 | 104.0 (2) | H15—C13—H16 | 109.5 |
C3—N5—Zn1 | 126.65 (17) | N9—C13—H17 | 109.5 |
C16—N5—Zn1 | 128.99 (16) | H15—C13—H17 | 109.5 |
C3ii—N6—C6 | 104.74 (19) | H16—C13—H17 | 109.5 |
C3ii—N6—Zn2 | 110.60 (15) | N8—C14—H18 | 109.5 |
C6—N6—Zn2 | 144.64 (17) | N8—C14—H19 | 109.5 |
C12—N7—C18 | 109.21 (19) | H18—C14—H19 | 109.5 |
C12—N7—C10 | 109.88 (19) | N8—C14—H20 | 109.5 |
C18—N7—C10 | 109.74 (19) | H18—C14—H20 | 109.5 |
N2—C1—N4 | 112.5 (2) | H19—C14—H20 | 109.5 |
N2—C1—C5 | 121.4 (2) | N9—C15—H21 | 109.5 |
N4—C1—C5 | 126.0 (2) | N9—C15—H22 | 109.5 |
C17—N8—C14 | 108.9 (2) | H21—C15—H22 | 109.5 |
C17—N8—C5 | 108.6 (2) | N9—C15—H23 | 109.5 |
C14—N8—C5 | 110.11 (18) | H21—C15—H23 | 109.5 |
C15—N9—C11 | 109.38 (19) | H22—C15—H23 | 109.5 |
C15—N9—C13 | 109.37 (19) | C6iii—C16—N5 | 109.3 (2) |
C11—N9—C13 | 110.07 (19) | C6iii—C16—H24 | 125.3 |
C15—N9—Zn2 | 116.67 (15) | N5—C16—H24 | 125.3 |
C11—N9—Zn2 | 104.92 (14) | N8—C17—H25 | 109.5 |
C13—N9—Zn2 | 106.24 (15) | N8—C17—H26 | 109.5 |
C7—C2—N2 | 108.4 (2) | H25—C17—H26 | 109.5 |
C7—C2—H1 | 125.8 | N8—C17—H27 | 109.5 |
N2—C2—H1 | 125.8 | H25—C17—H27 | 109.5 |
O3—N10—O5 | 153.6 (4) | H26—C17—H27 | 109.5 |
O3—N10—O4 | 61.2 (5) | N7—C18—H28 | 109.5 |
O5—N10—O4 | 123.1 (5) | N7—C18—H29 | 109.5 |
O3—N10—O6 | 67.3 (5) | H28—C18—H29 | 109.5 |
O5—N10—O6 | 120.8 (5) | N7—C18—H30 | 109.5 |
O4—N10—O6 | 115.1 (5) | H28—C18—H30 | 109.5 |
O3—N10—O1 | 124.1 (4) | H29—C18—H30 | 109.5 |
O5—N10—O1 | 49.4 (3) | O5—O1—N10 | 64.6 (3) |
O4—N10—O1 | 73.8 (4) | O5—O1—O4 | 117.3 (5) |
O6—N10—O1 | 168.6 (5) | N10—O1—O4 | 52.8 (3) |
O3—N10—O2 | 116.7 (4) | O5—O1—Zn1 | 67.8 (3) |
O5—N10—O2 | 72.1 (4) | N10—O1—Zn1 | 119.3 (3) |
O4—N10—O2 | 152.8 (5) | O4—O1—Zn1 | 141.3 (5) |
O6—N10—O2 | 50.3 (4) | O6—O2—N10 | 64.2 (4) |
O1—N10—O2 | 118.5 (4) | O6—O2—O5 | 116.0 (5) |
N5—C3—N6iii | 113.9 (2) | N10—O2—O5 | 53.3 (3) |
N5—C3—C11iii | 126.3 (2) | N10—O3—O4 | 59.7 (3) |
N6iii—C3—C11iii | 119.7 (2) | N10—O3—O6 | 56.7 (4) |
C8iv—C4—N1 | 108.1 (2) | O4—O3—O6 | 105.5 (6) |
C8iv—C4—H2 | 125.9 | N10—O4—O3 | 59.1 (4) |
N1—C4—H2 | 125.9 | N10—O4—O1 | 53.4 (3) |
N8—C5—C1 | 110.65 (18) | O3—O4—O1 | 105.2 (5) |
N8—C5—H3 | 109.5 | O1—O5—N10 | 66.0 (3) |
C1—C5—H3 | 109.5 | O1—O5—O2 | 117.5 (5) |
N8—C5—H4 | 109.5 | N10—O5—O2 | 54.6 (3) |
C1—C5—H4 | 109.5 | O1—O5—Zn1 | 84.3 (4) |
H3—C5—H4 | 108.1 | N10—O5—Zn1 | 132.0 (4) |
C16ii—C6—N6 | 107.9 (2) | O2—O5—Zn1 | 121.4 (4) |
C16ii—C6—H5 | 126.0 | O2—O6—N10 | 65.5 (4) |
N6—C6—H5 | 126.0 | O2—O6—O3 | 120.4 (6) |
C2—C7—N4 | 108.9 (2) | N10—O6—O3 | 56.0 (3) |
N5—Zn1—N1—C9 | 85.68 (19) | O3—N10—O1—Zn1 | −170.8 (3) |
N4—Zn1—N1—C9 | −60.98 (19) | O5—N10—O1—Zn1 | 41.6 (4) |
O5—Zn1—N1—C9 | −175.8 (2) | O4—N10—O1—Zn1 | −134.2 (5) |
O1—Zn1—N1—C9 | −172.0 (2) | O6—N10—O1—Zn1 | 8 (2) |
N5—Zn1—N1—C4 | −100.4 (2) | O2—N10—O1—Zn1 | 19.4 (6) |
N4—Zn1—N1—C4 | 113.0 (2) | N5—Zn1—O1—O5 | −52.8 (4) |
O5—Zn1—N1—C4 | −1.8 (3) | N4—Zn1—O1—O5 | 78.7 (4) |
O1—Zn1—N1—C4 | 1.9 (2) | N1—Zn1—O1—O5 | −172.5 (4) |
N3—Zn2—N2—C1 | −47.6 (2) | N5—Zn1—O1—N10 | −93.2 (3) |
N6—Zn2—N2—C1 | −164.67 (18) | N4—Zn1—O1—N10 | 38.4 (4) |
N9—Zn2—N2—C1 | 106.03 (18) | N1—Zn1—O1—N10 | 147.1 (4) |
N3—Zn2—N2—C2 | 132.1 (2) | O5—Zn1—O1—N10 | −40.4 (4) |
N6—Zn2—N2—C2 | 15.0 (2) | N5—Zn1—O1—O4 | −159.2 (5) |
N9—Zn2—N2—C2 | −74.3 (2) | N4—Zn1—O1—O4 | −27.6 (6) |
N2—Zn2—N3—C9i | −56.5 (2) | N1—Zn1—O1—O4 | 81.1 (5) |
N6—Zn2—N3—C9i | 60.37 (18) | O5—Zn1—O1—O4 | −106.4 (7) |
N9—Zn2—N3—C9i | 148.78 (16) | O3—N10—O2—O6 | 12.4 (7) |
N2—Zn2—N3—C8 | 126.6 (2) | O5—N10—O2—O6 | 165.4 (7) |
N6—Zn2—N3—C8 | −116.5 (2) | O4—N10—O2—O6 | −65.9 (12) |
N9—Zn2—N3—C8 | −28.1 (2) | O1—N10—O2—O6 | −177.1 (6) |
N5—Zn1—N4—C1 | 168.46 (17) | O3—N10—O2—O5 | −153.0 (4) |
N1—Zn1—N4—C1 | −44.8 (2) | O4—N10—O2—O5 | 128.7 (11) |
O5—Zn1—N4—C1 | 74.0 (2) | O6—N10—O2—O5 | −165.4 (7) |
O1—Zn1—N4—C1 | 45.7 (2) | O1—N10—O2—O5 | 17.6 (4) |
N5—Zn1—N4—C7 | −19.6 (2) | O5—N10—O3—O4 | 107.0 (11) |
N1—Zn1—N4—C7 | 127.07 (19) | O6—N10—O3—O4 | −138.9 (6) |
O5—Zn1—N4—C7 | −114.1 (2) | O1—N10—O3—O4 | 40.8 (6) |
O1—Zn1—N4—C7 | −142.4 (2) | O2—N10—O3—O4 | −149.2 (6) |
N4—Zn1—N5—C3 | −175.44 (18) | O5—N10—O3—O6 | −114.0 (11) |
N1—Zn1—N5—C3 | 41.3 (2) | O4—N10—O3—O6 | 138.9 (6) |
O5—Zn1—N5—C3 | −70.8 (3) | O1—N10—O3—O6 | 179.7 (5) |
O1—Zn1—N5—C3 | −48.9 (2) | O2—N10—O3—O6 | −10.3 (6) |
N4—Zn1—N5—C16 | 12.3 (2) | O5—N10—O4—O3 | −149.5 (5) |
N1—Zn1—N5—C16 | −130.93 (19) | O6—N10—O4—O3 | 42.0 (7) |
O5—Zn1—N5—C16 | 116.9 (3) | O1—N10—O4—O3 | −145.7 (5) |
O1—Zn1—N5—C16 | 138.8 (2) | O2—N10—O4—O3 | 92.9 (11) |
N2—Zn2—N6—C3ii | −133.67 (16) | O3—N10—O4—O1 | 145.7 (5) |
N3—Zn2—N6—C3ii | 98.02 (16) | O5—N10—O4—O1 | −3.8 (6) |
N9—Zn2—N6—C3ii | −15.66 (15) | O6—N10—O4—O1 | −172.3 (6) |
N2—Zn2—N6—C6 | 48.5 (3) | O2—N10—O4—O1 | −121.4 (10) |
N3—Zn2—N6—C6 | −79.8 (3) | O6—O3—O4—N10 | −34.8 (4) |
N9—Zn2—N6—C6 | 166.5 (3) | N10—O3—O4—O1 | −28.0 (4) |
C2—N2—C1—N4 | −0.1 (3) | O6—O3—O4—O1 | −62.7 (7) |
Zn2—N2—C1—N4 | 179.66 (15) | O5—O1—O4—N10 | 4.2 (6) |
C2—N2—C1—C5 | −177.7 (2) | Zn1—O1—O4—N10 | 92.1 (6) |
Zn2—N2—C1—C5 | 2.1 (3) | O5—O1—O4—O3 | 34.3 (9) |
C7—N4—C1—N2 | 0.0 (3) | N10—O1—O4—O3 | 30.1 (4) |
Zn1—N4—C1—N2 | 173.36 (15) | Zn1—O1—O4—O3 | 122.2 (6) |
C7—N4—C1—C5 | 177.4 (2) | O4—O1—O5—N10 | −3.7 (6) |
Zn1—N4—C1—C5 | −9.2 (3) | Zn1—O1—O5—N10 | −141.3 (3) |
N2—Zn2—N9—C15 | −108.29 (17) | N10—O1—O5—O2 | 18.7 (4) |
N3—Zn2—N9—C15 | 47.08 (19) | O4—O1—O5—O2 | 15.0 (8) |
N6—Zn2—N9—C15 | 149.58 (18) | Zn1—O1—O5—O2 | −122.6 (5) |
N2—Zn2—N9—C11 | 130.50 (14) | N10—O1—O5—Zn1 | 141.3 (3) |
N3—Zn2—N9—C11 | −74.13 (16) | O4—O1—O5—Zn1 | 137.5 (5) |
N6—Zn2—N9—C11 | 28.38 (14) | O3—N10—O5—O1 | −86.3 (10) |
N2—Zn2—N9—C13 | 13.91 (17) | O4—N10—O5—O1 | 4.8 (7) |
N3—Zn2—N9—C13 | 169.28 (14) | O6—N10—O5—O1 | 172.7 (6) |
N6—Zn2—N9—C13 | −88.21 (15) | O2—N10—O5—O1 | 159.6 (5) |
C1—N2—C2—C7 | 0.2 (3) | O3—N10—O5—O2 | 114.2 (10) |
Zn2—N2—C2—C7 | −179.52 (17) | O4—N10—O5—O2 | −154.8 (7) |
C16—N5—C3—N6iii | −0.6 (3) | O6—N10—O5—O2 | 13.1 (6) |
Zn1—N5—C3—N6iii | −174.38 (15) | O1—N10—O5—O2 | −159.6 (5) |
C16—N5—C3—C11iii | −177.3 (2) | O3—N10—O5—Zn1 | −143.2 (8) |
Zn1—N5—C3—C11iii | 8.8 (3) | O4—N10—O5—Zn1 | −52.1 (9) |
C9—N1—C4—C8iv | −0.3 (3) | O6—N10—O5—Zn1 | 115.8 (7) |
Zn1—N1—C4—C8iv | −175.00 (17) | O1—N10—O5—Zn1 | −56.9 (5) |
C17—N8—C5—C1 | 169.44 (19) | O2—N10—O5—Zn1 | 102.7 (6) |
C14—N8—C5—C1 | −71.4 (2) | O6—O2—O5—O1 | −35.7 (10) |
N2—C1—C5—N8 | −46.1 (3) | N10—O2—O5—O1 | −21.1 (5) |
N4—C1—C5—N8 | 136.6 (2) | O6—O2—O5—N10 | −14.7 (7) |
C3ii—N6—C6—C16ii | 0.3 (3) | O6—O2—O5—Zn1 | −136.5 (7) |
Zn2—N6—C6—C16ii | 178.2 (2) | N10—O2—O5—Zn1 | −121.9 (4) |
N2—C2—C7—N4 | −0.3 (3) | N5—Zn1—O5—O1 | 129.3 (4) |
C1—N4—C7—C2 | 0.2 (3) | N4—Zn1—O5—O1 | −110.3 (4) |
Zn1—N4—C7—C2 | −173.11 (16) | N1—Zn1—O5—O1 | 7.9 (5) |
C9i—N3—C8—C4i | 0.6 (3) | N5—Zn1—O5—N10 | 179.5 (6) |
Zn2—N3—C8—C4i | 177.79 (17) | N4—Zn1—O5—N10 | −60.0 (6) |
C4—N1—C9—N3iv | 0.7 (3) | N1—Zn1—O5—N10 | 58.2 (7) |
Zn1—N1—C9—N3iv | 176.01 (14) | O1—Zn1—O5—N10 | 50.3 (5) |
C4—N1—C9—C12 | −177.1 (2) | N5—Zn1—O5—O2 | −111.8 (5) |
Zn1—N1—C9—C12 | −1.7 (3) | N4—Zn1—O5—O2 | 8.7 (5) |
C15—N9—C11—C3ii | −161.6 (2) | N1—Zn1—O5—O2 | 126.9 (4) |
C13—N9—C11—C3ii | 78.2 (2) | O1—Zn1—O5—O2 | 118.9 (6) |
Zn2—N9—C11—C3ii | −35.8 (2) | O5—O2—O6—N10 | 13.0 (6) |
C18—N7—C12—C9 | 169.90 (19) | N10—O2—O6—O3 | −11.5 (6) |
C10—N7—C12—C9 | −69.7 (2) | O5—O2—O6—O3 | 1.5 (12) |
N3iv—C9—C12—N7 | 145.6 (2) | O3—N10—O6—O2 | −168.0 (7) |
N1—C9—C12—N7 | −36.9 (3) | O5—N10—O6—O2 | −16.3 (8) |
C3—N5—C16—C6iii | 0.7 (3) | O4—N10—O6—O2 | 152.5 (7) |
Zn1—N5—C16—C6iii | 174.34 (17) | O1—N10—O6—O2 | 13 (2) |
O3—N10—O1—O5 | 147.6 (5) | O5—N10—O6—O3 | 151.7 (5) |
O4—N10—O1—O5 | −175.8 (6) | O4—N10—O6—O3 | −39.5 (6) |
O6—N10—O1—O5 | −34 (2) | O1—N10—O6—O3 | −179 (73) |
O2—N10—O1—O5 | −22.2 (6) | O2—N10—O6—O3 | 168.0 (7) |
O3—N10—O1—O4 | −36.6 (6) | N10—O3—O6—O2 | 12.7 (7) |
O5—N10—O1—O4 | 175.8 (6) | O4—O3—O6—O2 | 48.8 (10) |
O6—N10—O1—O4 | 142 (2) | O4—O3—O6—N10 | 36.1 (5) |
O2—N10—O1—O4 | 153.6 (6) |
Symmetry codes: (i) x−y+1, x, z+1/6; (ii) x−y, x, z+1/6; (iii) y, −x+y, z−1/6; (iv) y, −x+y+1, z−1/6. |
Acknowledgements
Financial support from JSPS Grant-in-Aid for Scientific Research No. 26810037 is gratefully acknowledged.
References
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). SIR2002. University of Bari, Italy. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Crystallogr. Soc. Japan, 51, 218–224. CrossRef Google Scholar
Park, K. S., Ni, Z., Côté, A. P., Choi, J. Y., Huang, R., Uribe-Romo, F. J., Chae, H. K., O'Keeffe, M. & Yaghi, O. M. (2006). PNAS, 103, 10186–10191. CSD CrossRef PubMed CAS Google Scholar
Quan, M. L., Lam, P. Y. S., Han, Q., Pinto, D. J. P., He, M. Y., Li, R., Ellis, C. D., Clark, C. G., Teleha, C. A., Sun, J.-H., Alexander, R. S., Bai, S., Luettgen, J. M., Knabb, R. M., Wong, P. C. & Wexler, R. R. (2005). J. Med. Chem. 48, 1729–1744. CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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.