research communications
κO)dioxido{2-[3-(pyridin-2-yl-κN)-1H-1,2,4-triazol-5-yl-κN4]phenolato-κO}uranium(VI) acetonitrile monosolvate monohydrate
of aqua(nitrato-aDepartment of Chemistry, Taras Shevchenko National University of Kyiv, 64/13, Volodymyrska Str., Kyiv, 01601, Ukraine, and bSTC "Institute for Single Crystals", National Academy of Science of Ukraine, 60 Lenina Ave., Kharkiv 61001, Ukraine
*Correspondence e-mail: lana_@univ.kiev.ua
In the title compound, [U(C13H9N4O)(NO3)O2(H2O)]·CH3CN·H2O, the UVI atom is seven-coordinated in a distorted pentagonal–bipyramidal N2O5 manner by one tridentate triazole ligand, one monodentate nitrate anion and one water molecule in the equatorial plane and by two uranyl(VI) O atoms in the axial positions. In the crystal, the UVI complex molecule is linked to the water and acetonitrile solvent molecules through N—H⋯N, O—H⋯O and O—H⋯N hydrogen bonds, forming a sheet structure parallel to the bc plane. The sheets are further linked by an additional O—H⋯O hydrogen bond, forming a three-dimensional network.
Keywords: crystal structure; uranyl(VI) ion; 1,2,4-triazole.
CCDC reference: 1443165
1. Chemical context
The synthesis of coordination compounds with N-donor heterocyclic ligands is one of the fastest growing areas of coordination chemistry. 1,2,4-Triazoles and their derivatives can be assigned for such types of ligands. The presence of the 1,2,4-triazole ring in the organic ligand provides an additional site for coordination (Aromí et al., 2011). The presence of additional donor groups in the 3- and 5-positions of the triazole moiety provides a greater number of possibilities for of metal ions, involving tridentate bis-chelate functions.
It should be noted that UO22+ complexes with such types of ligands have rarely been investigated. Thus, only three uranyl complexes with 1,2,4-triazole derivatives have been characterized (Daro et al., 2001; Weng et al., 2012; Raspertova et al., 2012). As part of our continuing study of uranium coordination compounds with nitrogen-donor ligands (Raspertova et al., 2012), we report here the structure of the title compound.
2. Structural commentary
The VI atom in the title complex is a distorted pentagonal bipyramid. It is coordinated in a tridentate manner by the 1,2,4,-triazole ligand together with the water molecule and the monodentate nitrate anion in the equatorial plane. Two oxido ligands are placed in the axial positions (Fig. 1). The U1—O1 bond length [2.206 (3) Å] is comparable with those reported for related six-membered chelate fragments involving phenolate and N-atom donors (Sopo et al., 2008; Ahmadi et al., 2012). The U—N bond lengths [2.489 (4) and 2.658 (4) Å] are consistent with the situation in other pyridine-bonded uranium complexes (Amoroso et al., 1996; Gatto et al., 2004). The uranyl group is not exactly linear [O2=U1=O3 = 175.36 (14)°]. Non-linear O=U= groups are generally found in uranyl complexes with five non-symmetrically bonding equatorial ligands. All non-hydrogen atoms of the organic ligand are coplanar within 0.01 Å. The N1—C7 and C7—N2 bond lengths of the triazole ring are equalized [1.336 (5) Å for both]. This value is longer than a Csp2 =N double bond (1.276 Å) and shorter than a Csp2—N single bond (1.347 Å) (Orpen et al., 1994). It can be assumed that the structure of the triazole ring is the superposition of two possible resonance structures as shown in Fig. 2.
of the U3. Supramolecular features
In the crystal, the complex molecule is linked to the water and acetonitrile solvent molecules through N2—H2⋯N6, O4—H4B⋯O8, O8—H8A⋯N3ii and O8—H8B⋯O6iii hydrogen bonds (symmetry codes in Table 1), forming a sheet structure parallel to the bc plane. The sheets are further linked by an O4—H4A⋯O5i hydrogen bond (Table 1), forming a three-dimensional network (Fig. 3).
4. Database survey
In the Cambridge Structural Database (Version 5.36, November 2014; Groom & Allen, 2014), only three uranyl complexes with derivatives of 1,2,4-triazole are reported (Daro et al., 2001; Weng et al., 2012; Raspertova et al., 2012). 72 structures containing a 5-pyridin-1H-1,2,4-triazole fragment are found. A search for the 3-hydroxyphenyl-1,2,4-triazole fragment yielded 14 hits, including: 2,2′-[1-(2,4,6-trichlorophenyl)-1H-1,2,4-triazole-3,5-diyl]diphenol (Li et al., 2008); 2-[5-(2-pyridyl)-1,2,4-triazole-3-yl]phenol 2-[3-(2-pyridyl)-1,2,4-triazole-5-yl]phenol bis(7,7,8,8-tetracyanoquinodimethane) (Bentiss et al., 2002); bis[μ2-1-phenyl-3,5-bis(2-oxyphenyl)-1,2,4-triazole]bis(pyridine)dicopper (Steinhauser et al., 2004). Only one compound containing both hydroxyphenyl and pyridyl, as substituents in the 3- and 5-positions of 1,2,4-triazole, was found (Bentiss et al., 2002).
5. Synthesis and crystallization
A mixture of 3-(2-hydroxyphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazole (0.5 mmol) and [UO2(NO3)2]·2H2O (0.5 mmol) in acetonitrile (20 ml) was stirred for 20 min. The solution was left to evaporate slowly at room temperature. Red single crystals suitable for X-ray analysis were obtained after 2 d.
6. Refinement
Crystal data, data collection and structure . All hydrogen atoms were located in a difference Fourier map. The positional parameters of water H atoms were refined, with the restraint O—H = 0.860 (2) Å and the constraint Uiso(H) = 1.5Ueq(O). All other H atoms were constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N).
details are summarized in Table 2
|
Supporting information
CCDC reference: 1443165
10.1107/S205698901502438X/is5435sup1.cif
contains datablocks Global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S205698901502438X/is5435Isup2.hkl
The synthesis of coordination compounds with N-donor heterocyclic ligands is one of the fastest growing areas of coordination chemistry. 1,2,4-Triazoles and their derivatives can be assigned for such types of ligands. The presence of the 1,2,4-triazole ring in the organic ligand provides an additional site for coordination (Aromí et al., 2011). The presence of additional donor groups in the 3- and 5-positions of the triazole moiety provides a greater number of possibilities for
of metal ions, involving tridentate bis-chelate functions.It should be note that UO22+ complexes with such types of ligands have rarely been investigated. Thus, only three uranyl complexes with 1,2,4-triazole derivatives have been characterized (Daro et al., 2001; Weng et al., 2012; Raspertova et al., 2012). As part of our continuing study of uranium coordination compounds with nitrogen-donor ligands (Raspertova et al., 2012), we report here the structure of the title compound.
The ═U1═O3 = 175.36 (14)°]. Non-linear O═U═O bonds are generally found in uranyl complexes with five non-symmetrically bonding equatorial ligands. All non-hydrogen atoms of the organic ligand are coplanar within 0.01 Å. The N1—C7 and C7—N2 bond lengths of the triazole ring are equalized [1.336 (5) Å for both]. This value is longer than a Csp2 ═N double bond (1.276 Å) and shorter than a Csp2—N single bond (1.347 Å) (Orpen et al., 1994). It can be assumed that the structure of the triazole ring is the superposition of two resonance structures as shown in Fig. 2.
of the UVI atom in the title complex is a distorted pentagonal bipyramid. It is coordinated in a tridentate manner by the 1,2,4,-triazole ligand together with the water molecule and the monodentate nitrate anion in the equatorial plane. Two oxo ligands are placed in the axial positions (Fig. 1). The U1—O1 bond length [2.206 (3) Å] is comparable with those reported for related six-membered chelate fragments involving phenolate and N-atom donors (Sopo et al., 2008; Ahmadi et al., 2012). The U—N bond lengths [2.489 (4) and 2.658 (4) Å] are consistent with the situation in other pyridine-bonded uranium complexes (Amoroso et al., 1996; Gatto et al., 2004). The uranyl group is not exactly linear [O2In the crystal, the complex molecule is linked to the water and acetonitrile solvent molecules through N2—H2···N6, O4—H4B···O8, O8—H8A···N3ii and O8—H8B···O6iii hydrogen bonds (symmetry codes in Table 1), forming a sheet structure parallel to the bc plane. The sheets are further linked by an O4—H4A···O5i hydrogen bond (Table 1), forming a three-dimensional network (Fig. 3).
In the Cambridge Structural Database (Version 5.36, November 2014; Groom & Allen, 2014), only three uranyl complexes with derivatives of 1,2,4-triazole are reported (Daro et al., 2001; Weng et al., 2012; Raspertova et al., 2012). 72 structures containing a 5-pyridin-1H-1,2,4-triazole fragment are found. A search for the 3-hydroxyphenyl-1,2,4-triazole fragment yielded 14 hits, including: 2,2'-[1-(2,4,6-trichlorophenyl)-1H-1,2,4-triazole-3,5-diyl]diphenol (Li et al., 2008); 2-[5-(2-pyridyl)-1,2,4-triazole-3-yl]phenol 2-[3-(2-pyridyl)-1,2,4-triazole-5-yl]phenol bis(7,7,8,8-tetracyanoquinodimethane) (Bentiss et al., 2002); bis[µ2-1-phenyl-3,5-bis(2-oxyphenyl)-1,2,4-triazole]bis(pyridine)dicopper (Steinhauser et al., 2004). Only one compound containing both hydroxyphenyl and pyridyl, as substituents in the 3- and 5-positions of 1,2,4-triazole, was found (Bentiss et al., 2002).
A mixture of 3-(2-hydroxyphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazole (0.5 mmol) and [UO2(NO3)2]·2H2O (0.5 mmol) in acetonitrile (20 ml) was stirred for 20 min. The solution was left to evaporate slowly at room temperature. Red single crystals suitable for X-ray analysis were obtained after 2 d.
Crystal data, data collection and structure
details are summarized in Table 2. A l l hydrogen atoms were located in a difference Fourier map. The positional parameters of water H atoms were refined, with the restraint O—H = 0.860 (2) Å and the constraint Uiso(H) = 1.5Ueq(O). All other H atoms were constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N).The synthesis of coordination compounds with N-donor heterocyclic ligands is one of the fastest growing areas of coordination chemistry. 1,2,4-Triazoles and their derivatives can be assigned for such types of ligands. The presence of the 1,2,4-triazole ring in the organic ligand provides an additional site for coordination (Aromí et al., 2011). The presence of additional donor groups in the 3- and 5-positions of the triazole moiety provides a greater number of possibilities for
of metal ions, involving tridentate bis-chelate functions.It should be note that UO22+ complexes with such types of ligands have rarely been investigated. Thus, only three uranyl complexes with 1,2,4-triazole derivatives have been characterized (Daro et al., 2001; Weng et al., 2012; Raspertova et al., 2012). As part of our continuing study of uranium coordination compounds with nitrogen-donor ligands (Raspertova et al., 2012), we report here the structure of the title compound.
The ═U1═O3 = 175.36 (14)°]. Non-linear O═U═O bonds are generally found in uranyl complexes with five non-symmetrically bonding equatorial ligands. All non-hydrogen atoms of the organic ligand are coplanar within 0.01 Å. The N1—C7 and C7—N2 bond lengths of the triazole ring are equalized [1.336 (5) Å for both]. This value is longer than a Csp2 ═N double bond (1.276 Å) and shorter than a Csp2—N single bond (1.347 Å) (Orpen et al., 1994). It can be assumed that the structure of the triazole ring is the superposition of two resonance structures as shown in Fig. 2.
of the UVI atom in the title complex is a distorted pentagonal bipyramid. It is coordinated in a tridentate manner by the 1,2,4,-triazole ligand together with the water molecule and the monodentate nitrate anion in the equatorial plane. Two oxo ligands are placed in the axial positions (Fig. 1). The U1—O1 bond length [2.206 (3) Å] is comparable with those reported for related six-membered chelate fragments involving phenolate and N-atom donors (Sopo et al., 2008; Ahmadi et al., 2012). The U—N bond lengths [2.489 (4) and 2.658 (4) Å] are consistent with the situation in other pyridine-bonded uranium complexes (Amoroso et al., 1996; Gatto et al., 2004). The uranyl group is not exactly linear [O2In the crystal, the complex molecule is linked to the water and acetonitrile solvent molecules through N2—H2···N6, O4—H4B···O8, O8—H8A···N3ii and O8—H8B···O6iii hydrogen bonds (symmetry codes in Table 1), forming a sheet structure parallel to the bc plane. The sheets are further linked by an O4—H4A···O5i hydrogen bond (Table 1), forming a three-dimensional network (Fig. 3).
In the Cambridge Structural Database (Version 5.36, November 2014; Groom & Allen, 2014), only three uranyl complexes with derivatives of 1,2,4-triazole are reported (Daro et al., 2001; Weng et al., 2012; Raspertova et al., 2012). 72 structures containing a 5-pyridin-1H-1,2,4-triazole fragment are found. A search for the 3-hydroxyphenyl-1,2,4-triazole fragment yielded 14 hits, including: 2,2'-[1-(2,4,6-trichlorophenyl)-1H-1,2,4-triazole-3,5-diyl]diphenol (Li et al., 2008); 2-[5-(2-pyridyl)-1,2,4-triazole-3-yl]phenol 2-[3-(2-pyridyl)-1,2,4-triazole-5-yl]phenol bis(7,7,8,8-tetracyanoquinodimethane) (Bentiss et al., 2002); bis[µ2-1-phenyl-3,5-bis(2-oxyphenyl)-1,2,4-triazole]bis(pyridine)dicopper (Steinhauser et al., 2004). Only one compound containing both hydroxyphenyl and pyridyl, as substituents in the 3- and 5-positions of 1,2,4-triazole, was found (Bentiss et al., 2002).
For related literature, see: Ahmadi et al. (2012); Amoroso et al. (1996); Aromí et al. (2011); Bentiss et al. (2002); Orpen et al. (1994); Daro et al. (2001); Gatto et al. (2004); Groom & Allen (2014); Li et al. (2008); Raspertova et al. (2012); Sopo et al. (2008); Steinhauser et al. (2004); Weng et al. (2012).
A mixture of 3-(2-hydroxyphenyl)-5-(pyridin-2-yl)-1H-1,2,4-triazole (0.5 mmol) and [UO2(NO3)2]·2H2O (0.5 mmol) in acetonitrile (20 ml) was stirred for 20 min. The solution was left to evaporate slowly at room temperature. Red single crystals suitable for X-ray analysis were obtained after 2 d.
detailsCrystal data, data collection and structure
details are summarized in Table 2. A l l hydrogen atoms were located in a difference Fourier map. The positional parameters of water H atoms were refined, with the restraint O—H = 0.860 (2) Å and the constraint Uiso(H) = 1.5Ueq(O). All other H atoms were constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N).Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. The molecular structure of the title compound, shown with 50% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds. | |
Fig. 2. Scheme showing the resonance structures in the triazole ligand. | |
Fig. 3. Packing diagram of the title compound, viewed along the b axis. Intermolecular hydrogen bonds are shown as dashed lines. |
[U(C13H9N4O)(NO3)O2(H2O)]·CH3CN·H2O | F(000) = 1216 |
Mr = 646.37 | Dx = 2.216 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.0962 (3) Å | Cell parameters from 4414 reflections |
b = 7.87839 (17) Å | θ = 3.3–31.9° |
c = 20.4041 (4) Å | µ = 8.44 mm−1 |
β = 94.829 (2)° | T = 294 K |
V = 1937.57 (7) Å3 | Block, red |
Z = 4 | 0.5 × 0.3 × 0.2 mm |
Agilent Xcalibur, Sapphire3 diffractometer | 4446 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3936 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 16.1827 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −5→10 |
Tmin = 0.055, Tmax = 0.185 | l = −26→26 |
9385 measured reflections |
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0276P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4446 reflections | Δρmax = 1.81 e Å−3 |
284 parameters | Δρmin = −0.88 e Å−3 |
[U(C13H9N4O)(NO3)O2(H2O)]·CH3CN·H2O | V = 1937.57 (7) Å3 |
Mr = 646.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.0962 (3) Å | µ = 8.44 mm−1 |
b = 7.87839 (17) Å | T = 294 K |
c = 20.4041 (4) Å | 0.5 × 0.3 × 0.2 mm |
β = 94.829 (2)° |
Agilent Xcalibur, Sapphire3 diffractometer | 4446 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 3936 reflections with I > 2σ(I) |
Tmin = 0.055, Tmax = 0.185 | Rint = 0.032 |
9385 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 4 restraints |
wR(F2) = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 1.81 e Å−3 |
4446 reflections | Δρmin = −0.88 e Å−3 |
284 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
U1 | 0.81873 (2) | 0.51832 (2) | 0.40174 (2) | 0.01286 (6) | |
O1 | 0.7272 (3) | 0.2815 (4) | 0.37710 (15) | 0.0193 (7) | |
O2 | 0.6934 (2) | 0.6205 (4) | 0.41869 (15) | 0.0189 (7) | |
O3 | 0.9494 (2) | 0.4323 (4) | 0.38551 (15) | 0.0179 (6) | |
O4 | 0.9187 (2) | 0.7071 (4) | 0.47688 (15) | 0.0164 (6) | |
H4A | 0.9886 (8) | 0.709 (7) | 0.489 (2) | 0.025* | |
H4B | 0.890 (3) | 0.768 (5) | 0.5061 (16) | 0.025* | |
O5 | 0.8563 (2) | 0.3461 (4) | 0.50215 (14) | 0.0186 (7) | |
O6 | 0.8368 (3) | 0.2773 (4) | 0.60322 (15) | 0.0234 (7) | |
O7 | 0.7619 (3) | 0.5091 (4) | 0.56334 (18) | 0.0258 (8) | |
N1 | 0.7589 (3) | 0.5025 (4) | 0.28218 (18) | 0.0128 (7) | |
N2 | 0.6933 (3) | 0.4457 (5) | 0.18299 (18) | 0.0162 (7) | |
H2 | 0.6608 | 0.3920 | 0.1501 | 0.019* | |
N3 | 0.7399 (3) | 0.6016 (4) | 0.17900 (18) | 0.0159 (8) | |
N4 | 0.8707 (3) | 0.7819 (4) | 0.32904 (18) | 0.0134 (7) | |
N5 | 0.8162 (3) | 0.3796 (5) | 0.55859 (18) | 0.0174 (8) | |
N6 | 0.5829 (3) | 0.3255 (5) | 0.0595 (2) | 0.0266 (9) | |
C1 | 0.6794 (3) | 0.1782 (5) | 0.3324 (2) | 0.0138 (8) | |
C2 | 0.6414 (3) | 0.0177 (5) | 0.3517 (2) | 0.0184 (9) | |
H2A | 0.6503 | −0.0141 | 0.3957 | 0.022* | |
C3 | 0.5915 (3) | −0.0919 (5) | 0.3057 (2) | 0.0183 (9) | |
H3 | 0.5661 | −0.1965 | 0.3194 | 0.022* | |
C4 | 0.5781 (3) | −0.0498 (5) | 0.2396 (2) | 0.0166 (9) | |
H4 | 0.5443 | −0.1250 | 0.2090 | 0.020* | |
C5 | 0.6158 (3) | 0.1056 (5) | 0.2200 (2) | 0.0155 (9) | |
H5 | 0.6081 | 0.1343 | 0.1756 | 0.019* | |
C6 | 0.6654 (3) | 0.2206 (5) | 0.2653 (2) | 0.0126 (8) | |
C7 | 0.7042 (3) | 0.3861 (5) | 0.2445 (2) | 0.0114 (8) | |
C8 | 0.7785 (3) | 0.6308 (5) | 0.2401 (2) | 0.0142 (9) | |
C9 | 0.8385 (3) | 0.7813 (5) | 0.2635 (2) | 0.0142 (9) | |
C10 | 0.8617 (3) | 0.9142 (5) | 0.2225 (2) | 0.0163 (9) | |
H10 | 0.8386 | 0.9105 | 0.1778 | 0.020* | |
C11 | 0.9198 (3) | 1.0527 (6) | 0.2489 (2) | 0.0184 (9) | |
H11 | 0.9361 | 1.1435 | 0.2222 | 0.022* | |
C12 | 0.9532 (3) | 1.0555 (6) | 0.3147 (2) | 0.0169 (9) | |
H12 | 0.9923 | 1.1478 | 0.3331 | 0.020* | |
C13 | 0.9277 (3) | 0.9180 (5) | 0.3534 (2) | 0.0176 (9) | |
H13 | 0.9510 | 0.9201 | 0.3980 | 0.021* | |
C14 | 0.5369 (4) | 0.2758 (6) | 0.0120 (2) | 0.0199 (10) | |
C15 | 0.4767 (4) | 0.2097 (6) | −0.0472 (2) | 0.0271 (11) | |
H15A | 0.4567 | 0.3017 | −0.0767 | 0.041* | |
H15B | 0.4107 | 0.1531 | −0.0358 | 0.041* | |
H15C | 0.5227 | 0.1308 | −0.0682 | 0.041* | |
O8 | 0.8271 (3) | 0.9203 (5) | 0.55170 (19) | 0.0344 (9) | |
H8A | 0.811 (5) | 0.899 (8) | 0.5911 (11) | 0.052* | |
H8B | 0.844 (5) | 1.026 (2) | 0.554 (3) | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
U1 | 0.01190 (9) | 0.01556 (9) | 0.01102 (9) | 0.00016 (6) | 0.00039 (6) | −0.00106 (6) |
O1 | 0.0240 (17) | 0.0209 (15) | 0.0128 (16) | −0.0051 (14) | 0.0006 (13) | 0.0014 (13) |
O2 | 0.0149 (15) | 0.0223 (16) | 0.0193 (16) | 0.0039 (13) | 0.0005 (13) | 0.0015 (14) |
O3 | 0.0129 (14) | 0.0216 (15) | 0.0190 (17) | 0.0029 (13) | 0.0000 (13) | −0.0040 (14) |
O4 | 0.0138 (15) | 0.0233 (15) | 0.0120 (16) | 0.0025 (14) | −0.0002 (13) | −0.0054 (13) |
O5 | 0.0216 (16) | 0.0249 (16) | 0.0089 (15) | 0.0012 (13) | −0.0011 (13) | −0.0012 (13) |
O6 | 0.0261 (18) | 0.0266 (17) | 0.0173 (17) | 0.0002 (15) | 0.0008 (14) | 0.0083 (15) |
O7 | 0.0230 (17) | 0.0289 (18) | 0.0260 (19) | 0.0110 (14) | 0.0042 (15) | 0.0026 (15) |
N1 | 0.0115 (16) | 0.0133 (17) | 0.0135 (18) | 0.0012 (14) | 0.0007 (14) | 0.0015 (14) |
N2 | 0.0154 (17) | 0.0184 (17) | 0.0144 (19) | −0.0051 (15) | −0.0009 (15) | −0.0043 (16) |
N3 | 0.0167 (18) | 0.0177 (18) | 0.0134 (19) | −0.0033 (15) | 0.0017 (15) | 0.0001 (15) |
N4 | 0.0104 (16) | 0.0174 (17) | 0.0120 (18) | 0.0003 (14) | −0.0015 (14) | −0.0026 (15) |
N5 | 0.0140 (18) | 0.0236 (19) | 0.0150 (19) | −0.0034 (16) | 0.0033 (15) | 0.0007 (16) |
N6 | 0.027 (2) | 0.033 (2) | 0.019 (2) | −0.0034 (19) | −0.0013 (18) | −0.0018 (19) |
C1 | 0.0110 (19) | 0.0156 (19) | 0.015 (2) | 0.0022 (16) | 0.0003 (16) | −0.0033 (18) |
C2 | 0.012 (2) | 0.023 (2) | 0.020 (2) | 0.0018 (18) | 0.0005 (18) | 0.0047 (19) |
C3 | 0.013 (2) | 0.016 (2) | 0.027 (3) | −0.0022 (18) | 0.0048 (19) | −0.0059 (19) |
C4 | 0.013 (2) | 0.016 (2) | 0.020 (2) | −0.0016 (18) | −0.0021 (17) | −0.0070 (19) |
C5 | 0.0103 (19) | 0.020 (2) | 0.017 (2) | 0.0040 (17) | 0.0032 (17) | −0.0005 (18) |
C6 | 0.0065 (18) | 0.017 (2) | 0.015 (2) | 0.0020 (16) | 0.0026 (16) | 0.0008 (17) |
C7 | 0.0084 (18) | 0.0141 (19) | 0.012 (2) | 0.0010 (16) | 0.0011 (16) | −0.0027 (17) |
C8 | 0.0112 (19) | 0.018 (2) | 0.014 (2) | 0.0017 (17) | 0.0039 (17) | 0.0002 (18) |
C9 | 0.0075 (19) | 0.020 (2) | 0.016 (2) | 0.0015 (17) | 0.0026 (17) | −0.0018 (18) |
C10 | 0.013 (2) | 0.023 (2) | 0.014 (2) | −0.0004 (18) | 0.0044 (17) | −0.0014 (19) |
C11 | 0.014 (2) | 0.020 (2) | 0.022 (2) | −0.0016 (18) | 0.0037 (18) | 0.004 (2) |
C12 | 0.013 (2) | 0.0138 (19) | 0.024 (2) | −0.0029 (17) | 0.0018 (18) | −0.0033 (19) |
C13 | 0.013 (2) | 0.017 (2) | 0.022 (2) | −0.0021 (18) | 0.0002 (18) | −0.0036 (19) |
C14 | 0.019 (2) | 0.022 (2) | 0.020 (2) | −0.0022 (19) | 0.0042 (19) | 0.001 (2) |
C15 | 0.030 (3) | 0.029 (3) | 0.022 (3) | −0.007 (2) | −0.002 (2) | 0.000 (2) |
O8 | 0.049 (2) | 0.0243 (18) | 0.033 (2) | 0.0018 (18) | 0.0193 (19) | −0.0056 (18) |
U1—O1 | 2.206 (3) | C2—H2A | 0.9300 |
U1—O2 | 1.776 (3) | C2—C3 | 1.376 (6) |
U1—O3 | 1.777 (3) | C3—H3 | 0.9300 |
U1—O4 | 2.390 (3) | C3—C4 | 1.386 (6) |
U1—O5 | 2.467 (3) | C4—H4 | 0.9300 |
U1—N1 | 2.489 (4) | C4—C5 | 1.378 (6) |
U1—N4 | 2.658 (4) | C5—H5 | 0.9300 |
O1—C1 | 1.319 (5) | C5—C6 | 1.394 (6) |
O4—H4A | 0.860 (2) | C6—C7 | 1.461 (5) |
O4—H4B | 0.860 (2) | C8—C9 | 1.451 (6) |
O5—N5 | 1.313 (4) | C9—C10 | 1.385 (6) |
O6—N5 | 1.226 (5) | C10—H10 | 0.9300 |
O7—N5 | 1.221 (5) | C10—C11 | 1.383 (6) |
N1—C7 | 1.336 (5) | C11—H11 | 0.9300 |
N1—C8 | 1.360 (5) | C11—C12 | 1.368 (6) |
N2—H2 | 0.8600 | C12—H12 | 0.9300 |
N2—N3 | 1.357 (5) | C12—C13 | 1.391 (6) |
N2—C7 | 1.336 (5) | C13—H13 | 0.9300 |
N3—C8 | 1.314 (5) | C14—C15 | 1.453 (6) |
N4—C9 | 1.360 (5) | C15—H15A | 0.9600 |
N4—C13 | 1.347 (5) | C15—H15B | 0.9600 |
N6—C14 | 1.146 (6) | C15—H15C | 0.9600 |
C1—C2 | 1.413 (6) | O8—H8A | 0.860 (2) |
C1—C6 | 1.405 (6) | O8—H8B | 0.860 (2) |
O1—U1—O4 | 152.83 (11) | C3—C2—C1 | 120.4 (4) |
O1—U1—O5 | 77.17 (10) | C3—C2—H2A | 119.8 |
O1—U1—N1 | 68.61 (11) | C2—C3—H3 | 119.3 |
O1—U1—N4 | 132.17 (11) | C2—C3—C4 | 121.5 (4) |
O2—U1—O1 | 90.45 (12) | C4—C3—H3 | 119.3 |
O2—U1—O3 | 175.36 (14) | C3—C4—H4 | 120.6 |
O2—U1—O4 | 89.24 (12) | C5—C4—C3 | 118.8 (4) |
O2—U1—O5 | 100.84 (12) | C5—C4—H4 | 120.6 |
O2—U1—N1 | 91.78 (13) | C4—C5—H5 | 119.3 |
O2—U1—N4 | 90.02 (12) | C4—C5—C6 | 121.3 (4) |
O3—U1—O1 | 94.15 (13) | C6—C5—H5 | 119.3 |
O3—U1—O4 | 86.96 (12) | C1—C6—C7 | 118.7 (4) |
O3—U1—O5 | 80.83 (12) | C5—C6—C1 | 120.1 (4) |
O3—U1—N1 | 89.32 (13) | C5—C6—C7 | 121.2 (4) |
O3—U1—N4 | 86.43 (13) | N1—C7—C6 | 126.9 (4) |
O4—U1—O5 | 76.21 (10) | N2—C7—N1 | 107.7 (4) |
O4—U1—N1 | 138.56 (11) | N2—C7—C6 | 125.3 (4) |
O4—U1—N4 | 75.00 (11) | N1—C8—C9 | 120.5 (4) |
O5—U1—N1 | 143.57 (10) | N3—C8—N1 | 113.7 (4) |
O5—U1—N4 | 149.01 (10) | N3—C8—C9 | 125.7 (4) |
N1—U1—N4 | 63.57 (10) | N4—C9—C8 | 114.9 (4) |
C1—O1—U1 | 149.5 (3) | N4—C9—C10 | 122.4 (4) |
U1—O4—H4A | 129 (4) | C10—C9—C8 | 122.7 (4) |
U1—O4—H4B | 126 (3) | C9—C10—H10 | 120.6 |
H4A—O4—H4B | 104 (4) | C11—C10—C9 | 118.8 (4) |
N5—O5—U1 | 124.2 (2) | C11—C10—H10 | 120.6 |
C7—N1—U1 | 133.5 (3) | C10—C11—H11 | 120.2 |
C7—N1—C8 | 104.5 (4) | C12—C11—C10 | 119.6 (4) |
C8—N1—U1 | 122.0 (3) | C12—C11—H11 | 120.2 |
N3—N2—H2 | 124.3 | C11—C12—H12 | 120.5 |
C7—N2—H2 | 124.3 | C11—C12—C13 | 119.0 (4) |
C7—N2—N3 | 111.5 (3) | C13—C12—H12 | 120.5 |
C8—N3—N2 | 102.6 (3) | N4—C13—C12 | 122.7 (4) |
C9—N4—U1 | 118.9 (3) | N4—C13—H13 | 118.6 |
C13—N4—U1 | 123.6 (3) | C12—C13—H13 | 118.6 |
C13—N4—C9 | 117.5 (4) | N6—C14—C15 | 178.4 (5) |
O6—N5—O5 | 116.9 (4) | C14—C15—H15A | 109.5 |
O7—N5—O5 | 118.6 (4) | C14—C15—H15B | 109.5 |
O7—N5—O6 | 124.6 (4) | C14—C15—H15C | 109.5 |
O1—C1—C2 | 119.5 (4) | H15A—C15—H15B | 109.5 |
O1—C1—C6 | 122.5 (4) | H15A—C15—H15C | 109.5 |
C6—C1—C2 | 118.0 (4) | H15B—C15—H15C | 109.5 |
C1—C2—H2A | 119.8 | H8A—O8—H8B | 102 (6) |
U1—O1—C1—C2 | 172.3 (4) | C1—C6—C7—N1 | 4.2 (6) |
U1—O1—C1—C6 | −7.1 (8) | C1—C6—C7—N2 | −177.7 (4) |
U1—O5—N5—O6 | 175.9 (2) | C2—C1—C6—C5 | −0.3 (6) |
U1—O5—N5—O7 | −4.3 (5) | C2—C1—C6—C7 | 180.0 (4) |
U1—N1—C7—N2 | 179.1 (3) | C2—C3—C4—C5 | −0.1 (6) |
U1—N1—C7—C6 | −2.6 (6) | C3—C4—C5—C6 | −0.8 (6) |
U1—N1—C8—N3 | −179.2 (3) | C4—C5—C6—C1 | 1.0 (6) |
U1—N1—C8—C9 | 1.8 (5) | C4—C5—C6—C7 | −179.3 (4) |
U1—N4—C9—C8 | −0.6 (4) | C5—C6—C7—N1 | −175.5 (4) |
U1—N4—C9—C10 | 179.5 (3) | C5—C6—C7—N2 | 2.6 (6) |
U1—N4—C13—C12 | −179.3 (3) | C6—C1—C2—C3 | −0.6 (6) |
O1—C1—C2—C3 | −180.0 (4) | C7—N1—C8—N3 | −0.1 (5) |
O1—C1—C6—C5 | 179.0 (4) | C7—N1—C8—C9 | −179.2 (4) |
O1—C1—C6—C7 | −0.7 (6) | C7—N2—N3—C8 | 0.1 (4) |
N1—C8—C9—N4 | −0.7 (5) | C8—N1—C7—N2 | 0.2 (4) |
N1—C8—C9—C10 | 179.2 (4) | C8—N1—C7—C6 | 178.5 (4) |
N2—N3—C8—N1 | 0.0 (4) | C8—C9—C10—C11 | −179.8 (4) |
N2—N3—C8—C9 | 179.0 (4) | C9—N4—C13—C12 | 0.6 (6) |
N3—N2—C7—N1 | −0.2 (5) | C9—C10—C11—C12 | 0.1 (6) |
N3—N2—C7—C6 | −178.6 (4) | C10—C11—C12—C13 | 0.0 (6) |
N3—C8—C9—N4 | −179.6 (4) | C11—C12—C13—N4 | −0.4 (6) |
N3—C8—C9—C10 | 0.2 (6) | C13—N4—C9—C8 | 179.4 (4) |
N4—C9—C10—C11 | 0.1 (6) | C13—N4—C9—C10 | −0.4 (6) |
C1—C2—C3—C4 | 0.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O5i | 0.86 (1) | 1.92 (2) | 2.752 (4) | 162 (5) |
O4—H4B···O8 | 0.86 (1) | 1.73 (1) | 2.581 (5) | 168 (5) |
N2—H2···N6 | 0.86 | 2.07 | 2.909 (5) | 165 |
O8—H8A···N3ii | 0.86 (1) | 2.05 (2) | 2.890 (5) | 164 (6) |
O8—H8B···O6iii | 0.86 (1) | 2.22 (3) | 3.001 (5) | 150 (6) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O5i | 0.860 (2) | 1.920 (16) | 2.752 (4) | 162 (5) |
O4—H4B···O8 | 0.860 (2) | 1.733 (10) | 2.581 (5) | 168 (5) |
N2—H2···N6 | 0.86 | 2.07 | 2.909 (5) | 165 |
O8—H8A···N3ii | 0.860 (2) | 2.053 (18) | 2.890 (5) | 164 (6) |
O8—H8B···O6iii | 0.860 (2) | 2.22 (3) | 3.001 (5) | 150 (6) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [U(C13H9N4O)(NO3)O2(H2O)]·CH3CN·H2O |
Mr | 646.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 12.0962 (3), 7.87839 (17), 20.4041 (4) |
β (°) | 94.829 (2) |
V (Å3) | 1937.57 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 8.44 |
Crystal size (mm) | 0.5 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Agilent Xcalibur, Sapphire3 |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2014) |
Tmin, Tmax | 0.055, 0.185 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9385, 4446, 3936 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.064, 1.05 |
No. of reflections | 4446 |
No. of parameters | 284 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.81, −0.88 |
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009).
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