research communications
N-hydroxypicolinamide monohydrate
ofaDepartment of Chemistry, National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, 01601 Kiev, Ukraine, and bSSI "Institute for Single Crystals", National Academy of Sciences of Ukraine, Lenina ave. 60, Kharkiv 61001, Ukraine
*Correspondence e-mail: safyanova_inna@mail.ru
The 6H6N2O2·H2O, consists of N-hydroxypicolinamide and water molecules connected through O—H⋯O and N—H⋯N hydrogen bonds. The O—H⋯O interactions and π–π stacking interactions between the pyridine rings [centroid–centroid distance = 3.427 (1) Å] organize the components into columns extending along the b axis and the N—H⋯N hydrogen bonds link these columns into a two-dimensional framework parallel to (100). The N-hydroxypicolinamide molecule adopts a strongly flattened conformation and only the O—H group H atom deviates significantly from the molecule best plane. The dihedral angle between the hydroxamic group and the pyridine ring is 5.6 (2)°. The conformation about the hydroxamic group C—N bond is Z and that about the C—C bond between the pyridine and hydroxamic groups is E.
of the title compound, CCCDC reference: 1444026
1. Chemical context
R—C(=O)—NH—OH. HA can exist as keto and imino(enol) tautomers with two isomers, E and Z, for each form, and in the zwitterionic form (see Scheme below). They have found broad application in coordination chemistry due to their diversity and comparatively facile synthesis (Świątek-Kozłowska et al., 2000; Dobosz et al., 1999). In addition, they exhibit biological activities related to their enzyme-inhibitory properties (Marmion et al., 2013). HAs are widely used in coordination and supramolecular chemistry as scaffolds in the preparation of metallacrowns (Seda et al., 2007; Jankolovits et al., 2013; Safyanova et al., 2015) and as building blocks of coordination polymers (Gumienna-Kontecka et al., 2007; Golenya et al., 2014; Pavlishchuk et al., 2010, 2011).
(HA) are weak organic acids with the general formulaN-Hydroxypicolinamide, known also as picoline-2-hydroxamic acid (o-PicHA), has been used extensively for the synthesis of polynuclear complexes, especially in the synthesis of diverse metallacrowns (Stemmler et al., 1999; Seda et al., 2007; Jankolovits et al., 2013; Golenya et al., 2012; Gumienna-Kontecka et al., 2013). Presently, the Cambridge Structural Database (Groom & Allen, 2014) contains more than 20 entries of coordination compounds based on N-hydroxypicolinamide.
Our interest in N-hydroxypicolinamide stems also from the fact that in the course of synthesis of the title and related compounds from 2-picolinic acid (Hynes, 1970), the products are frequently contaminated with impurities that result from hydrolysis of the ester or hydroxamic groups to the carboxylic group. Structural information about the title compound will be helpful in controlling the purity of the synthesised ligand by powder diffraction.
2. Structural commentary
The molecular structure of the title compound is presented in Fig. 1. The of the title compound consists of an N-hydroxypicolinamide molecule in the Z-keto tautomeric form in agreement with the C=O and C—N bond lengths [1.234 (2) and 1.325 (2) Å, respectively] and a water molecule. The N-hydroxypicolinamide molecule adopts a strongly flattened conformation and only the O—H group H atom deviates significantly from the molecular best plane. The maximum deviation from this plane for non-hydrogen atom is 0.083 (1) Å for O1 and the hydroxyl group H2 atom is displaced from the mean plane by 0.80 (1) Å in the direction of the water molecule. The dihedral angle between the hydroxamic group and the pyridine ring is 5.6 (2)°. The configuration about the hydroxamic group C—N bond is Z and that about the C—C bond between the pyridine and hydroxamic groups is E [torsion angles O2—N2—C6—O1 −0.4 (3)°, N1—C1—C6—O1 175.6 (2)°].
3. Supramolecular features
The molecular components of the title compound are connected by O—H⋯O and N—H⋯N hydrogen bonds (Table 1) into a two-dimensional framework parallel to (100) (Fig. 2). The O—H⋯O interactions and π–π stacking interactions between the pyridine rings [centroid–centroid distance 3.427 (1) Å] organize the crystal components into columns extending along the b axis while the N—H⋯N hydrogen bonds link these columns into a two-dimensional framework parallel to (100) (Fig.2).
4. Database survey
A search of the Cambridge Structural Database (Version 5.36, last update February 2015; Groom & Allen, 2014) revealed two crystal structures of isomeric pyridine and the of 2,6-pyridinedihydroxamic acid (Golenya et al., 2007; Makhmudova et al., 2001; Griffith et al., 2008).
5. Synthesis and crystallization
The title compound was obtained by the reaction of methyl 2-picolinate and hydroxylamine in methanol solution according to a reported procedure (Hynes, 1970). Colorless crystals suitable for X-ray diffraction were obtained from a methanol solution by slow evaporation at room temperature (yield 79%).
6. Refinement
Crystal data, data collection and structure . The crystal was modelled as a non-merohedral twin with the volume ratio of two twin domains refined at 89:19. The C—H, N—H and O—H hydrogen atoms of the organic molecule were found from the difference Fourier maps but for further calculations they were positioned geometrically and constrained to ride on their parent atoms with C—H = 0.93 Å, N—H = 0.86 Å and O—H = 0.82 Å, and with Uiso = 1.2Ueq(C,N) or Uiso = 1.5Ueq(O). The H atoms of the water molecule were located in the difference Fourier maps, the O—H distances standardized to 0.85 Å and refined in riding-model approximation with Uiso(H) = 1.5Ueq(O).
details are summarized in Table 2Supporting information
CCDC reference: 1444026
10.1107/S2056989015024706/gk2650sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015024706/gk2650Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015024706/gk2650Isup3.cml
Hydroxamic acids (HA) are weak organic acids with the general formula R—C(═O)—NH—OH. HA can exist as keto and imino(enol) tautomers with two isomers, E and Z, for each form, and in the zwitterionic form (see Scheme below). They have found broad application in coordination chemistry due to their diversity and comparatively facile synthesis (Świątek-Kozłowska et al., 2000; Dobosz et al., 1999). In addition, they exhibit biological activities related to their enzyme-inhibitory properties (Marmion et al., 2013). HA are widely used in coordination and supramolecular chemistry as scaffolds in the preparation of metallacrowns (Seda et al., 2007; Jankolovits et al., 2013; Safyanova et al., 2015) and as building blocks of coordination polymers (Gumienna-Kontecka et al., 2007; Golenya et al., 2014; Pavlishchuk et al., 2010, 2011).
N-Hydroxypicolinamide, known also as picoline-2-hydroxamic acid (o-PicHA), has been used extensively for the synthesis of polynuclear complexes, especially in the synthesis of diverse metallacrowns (Stemmler et al., 1999; Seda et al., 2007; Jankolovits et al., 2013; Golenya et al., 2012; Gumienna-Kontecka et al., 2013). Presently, the Cambridge Structural Database (Groom & Allen, 2014) contains more than 20 entries of coordination compounds based on N-hydroxypicolinamide.
Our interest in N-hydroxypicolinamide stems also from the fact that in the course of synthesis of the title and related compounds from 2-picolinic acid
(Hynes, 1970), the products are frequently contaminated with impurities that result from hydrolysis of the ester or hydroxamic groups to the carboxylic group. Structural information about the title compound will be helpful in controlling the purity of the synthesized ligand by powder diffraction.The molecular structure of the title compound is presented in Fig. 1. The
of the title compound consists of an N-hydroxypicolinamide molecule in the Z-keto tautomeric form and a water molecule. The N-hydroxypicolinamide molecule adopts a strongly flattened conformation and only the O—H group H atom deviates significantly from the molecular best plane. The maximum deviation from this plane for non-hydrogen atom is 0.083 (1) Å for O1 and the hydroxyl group H2 atom is displaced from the mean plane by 0.80 (1) Å in the direction of the water molecule. The dihedral angle between the hydroxamic group and the pyridine ring is 5.6 (2)°. The configuration about the hydroxamic group C—N bond is Z and that about the C—C bond between the pyridine and hydroxamic groups is E [torsion angles O2—N2—C6—O1 − 0.4 (3)°, N1—C1—C6—O1 175.6 (2)°].The molecular components of the title compound are connected by O—H···O and N—H···N hydrogen bonds (Table 1) into a two-dimensional framework parallel to (100) (Fig. 2). The O—H···O interactions and π–π stacking interactions between the pyridine rings [centroid–centroid distance 3.427 (1) Å] organize the crystal components into columns extending along the b axis while the N—H···N hydrogen bonds link these columns into a two-dimensional framework parallel to (100) (Fig.2).
A search of the Cambridge Structural Database (Version 5.36, last update February 2015; Groom & Allen, 2014) reveals two crystal structures of isomeric pyridine
and the of 2,6-pyridinedihydroxamic acid (Golenya et al., 2007; Makhmudova et al., 2001; Griffith et al., 2008).The title compound was obtained by the reaction of methyl 2-picolinate and hydroxylamine in methanol according to a reported procedure (Hynes, 1970). Colorless crystals suitable for X-ray diffraction were obtained from a methanol solution by slow evaporation at room temperature (yield 79%).
Crystal data, data collection and structure
details are summarized in Table 2. The crystal was refined as a non-merohedral twin with the volume ratio of two twin domains refined at 89:19. The C—H, N—H and O—H hydrogen atoms of the organic molecule were found from the difference Fourier maps but for further calculations they were positioned geometrically and constrained to ride on their parent atoms with C—H = 0.93 Å, N—H = 0.86 Å and O—H = 0.82 Å, and with Uiso = 1.2Ueq(C,N) or Uiso = 1.5Ueq(O). The H atoms of the water molecule were located in the difference Fourier maps, the O—H distances standardized to 0.85 Å and refined in riding-model approximation with Uiso(H) = 1.5Ueq(O).Hydroxamic acids (HA) are weak organic acids with the general formula R—C(═O)—NH—OH. HA can exist as keto and imino(enol) tautomers with two isomers, E and Z, for each form, and in the zwitterionic form (see Scheme below). They have found broad application in coordination chemistry due to their diversity and comparatively facile synthesis (Świątek-Kozłowska et al., 2000; Dobosz et al., 1999). In addition, they exhibit biological activities related to their enzyme-inhibitory properties (Marmion et al., 2013). HA are widely used in coordination and supramolecular chemistry as scaffolds in the preparation of metallacrowns (Seda et al., 2007; Jankolovits et al., 2013; Safyanova et al., 2015) and as building blocks of coordination polymers (Gumienna-Kontecka et al., 2007; Golenya et al., 2014; Pavlishchuk et al., 2010, 2011).
N-Hydroxypicolinamide, known also as picoline-2-hydroxamic acid (o-PicHA), has been used extensively for the synthesis of polynuclear complexes, especially in the synthesis of diverse metallacrowns (Stemmler et al., 1999; Seda et al., 2007; Jankolovits et al., 2013; Golenya et al., 2012; Gumienna-Kontecka et al., 2013). Presently, the Cambridge Structural Database (Groom & Allen, 2014) contains more than 20 entries of coordination compounds based on N-hydroxypicolinamide.
Our interest in N-hydroxypicolinamide stems also from the fact that in the course of synthesis of the title and related compounds from 2-picolinic acid
(Hynes, 1970), the products are frequently contaminated with impurities that result from hydrolysis of the ester or hydroxamic groups to the carboxylic group. Structural information about the title compound will be helpful in controlling the purity of the synthesized ligand by powder diffraction.The molecular structure of the title compound is presented in Fig. 1. The
of the title compound consists of an N-hydroxypicolinamide molecule in the Z-keto tautomeric form and a water molecule. The N-hydroxypicolinamide molecule adopts a strongly flattened conformation and only the O—H group H atom deviates significantly from the molecular best plane. The maximum deviation from this plane for non-hydrogen atom is 0.083 (1) Å for O1 and the hydroxyl group H2 atom is displaced from the mean plane by 0.80 (1) Å in the direction of the water molecule. The dihedral angle between the hydroxamic group and the pyridine ring is 5.6 (2)°. The configuration about the hydroxamic group C—N bond is Z and that about the C—C bond between the pyridine and hydroxamic groups is E [torsion angles O2—N2—C6—O1 − 0.4 (3)°, N1—C1—C6—O1 175.6 (2)°].The molecular components of the title compound are connected by O—H···O and N—H···N hydrogen bonds (Table 1) into a two-dimensional framework parallel to (100) (Fig. 2). The O—H···O interactions and π–π stacking interactions between the pyridine rings [centroid–centroid distance 3.427 (1) Å] organize the crystal components into columns extending along the b axis while the N—H···N hydrogen bonds link these columns into a two-dimensional framework parallel to (100) (Fig.2).
A search of the Cambridge Structural Database (Version 5.36, last update February 2015; Groom & Allen, 2014) reveals two crystal structures of isomeric pyridine
and the of 2,6-pyridinedihydroxamic acid (Golenya et al., 2007; Makhmudova et al., 2001; Griffith et al., 2008).The title compound was obtained by the reaction of methyl 2-picolinate and hydroxylamine in methanol according to a reported procedure (Hynes, 1970). Colorless crystals suitable for X-ray diffraction were obtained from a methanol solution by slow evaporation at room temperature (yield 79%).
detailsCrystal data, data collection and structure
details are summarized in Table 2. The crystal was refined as a non-merohedral twin with the volume ratio of two twin domains refined at 89:19. The C—H, N—H and O—H hydrogen atoms of the organic molecule were found from the difference Fourier maps but for further calculations they were positioned geometrically and constrained to ride on their parent atoms with C—H = 0.93 Å, N—H = 0.86 Å and O—H = 0.82 Å, and with Uiso = 1.2Ueq(C,N) or Uiso = 1.5Ueq(O). The H atoms of the water molecule were located in the difference Fourier maps, the O—H distances standardized to 0.85 Å and refined in riding-model approximation with Uiso(H) = 1.5Ueq(O).Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); 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 asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius. The dashed line indicates a hydrogen bond. | |
Fig. 2. A packing diagram of the title compound. Hydrogen bonds are indicated by dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. |
C6H6N2O2·H2O | Dx = 1.441 Mg m−3 |
Mr = 156.14 | Melting point: 393 K |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.7471 (13) Å | Cell parameters from 893 reflections |
b = 3.8129 (4) Å | θ = 4.1–29.0° |
c = 20.4813 (17) Å | µ = 0.12 mm−1 |
β = 100.570 (7)° | T = 298 K |
V = 1439.2 (2) Å3 | Plate, clear colourless |
Z = 8 | 0.4 × 0.4 × 0.1 mm |
F(000) = 656 |
Agilent Xcalibur, Sapphire3 diffractometer | 1401 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1053 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 16.1827 pixels mm-1 | θmax = 26.0°, θmin = 3.3° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −4→4 |
Tmin = 0.476, Tmax = 1.000 | l = −24→24 |
2491 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0751P)2] where P = (Fo2 + 2Fc2)/3 |
1401 reflections | (Δ/σ)max < 0.001 |
102 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C6H6N2O2·H2O | V = 1439.2 (2) Å3 |
Mr = 156.14 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 18.7471 (13) Å | µ = 0.12 mm−1 |
b = 3.8129 (4) Å | T = 298 K |
c = 20.4813 (17) Å | 0.4 × 0.4 × 0.1 mm |
β = 100.570 (7)° |
Agilent Xcalibur, Sapphire3 diffractometer | 1401 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 1053 reflections with I > 2σ(I) |
Tmin = 0.476, Tmax = 1.000 | Rint = 0.037 |
2491 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.19 e Å−3 |
1401 reflections | Δρmin = −0.25 e Å−3 |
102 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. |
Refinement. Refined as a 2-component twin. 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.52649 (8) | 0.3700 (4) | 0.43254 (7) | 0.0468 (5) | |
O2 | 0.40179 (7) | 0.5190 (5) | 0.35109 (7) | 0.0506 (5) | |
H2 | 0.3916 | 0.6429 | 0.3808 | 0.076* | |
N1 | 0.59448 (9) | 0.8106 (5) | 0.30306 (8) | 0.0366 (5) | |
N2 | 0.46909 (9) | 0.6163 (5) | 0.33806 (8) | 0.0410 (5) | |
H2A | 0.4722 | 0.7305 | 0.3025 | 0.049* | |
C1 | 0.59810 (10) | 0.6575 (5) | 0.36271 (9) | 0.0323 (5) | |
C2 | 0.66231 (11) | 0.6152 (6) | 0.40743 (11) | 0.0428 (6) | |
H2B | 0.6628 | 0.5119 | 0.4487 | 0.051* | |
C3 | 0.72601 (11) | 0.7308 (6) | 0.38915 (13) | 0.0519 (7) | |
H3 | 0.7703 | 0.7030 | 0.4178 | 0.062* | |
C4 | 0.72296 (11) | 0.8863 (6) | 0.32857 (13) | 0.0482 (6) | |
H4 | 0.7650 | 0.9656 | 0.3154 | 0.058* | |
C5 | 0.65653 (12) | 0.9234 (6) | 0.28737 (11) | 0.0434 (6) | |
H5 | 0.6549 | 1.0327 | 0.2465 | 0.052* | |
C6 | 0.52864 (10) | 0.5321 (6) | 0.38079 (9) | 0.0332 (5) | |
O1W | 0.39862 (8) | 0.9488 (5) | 0.45255 (8) | 0.0501 (5) | |
H1WA | 0.4308 | 1.0938 | 0.4455 | 0.075* | |
H1WB | 0.4202 | 0.8351 | 0.4861 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0447 (8) | 0.0657 (11) | 0.0287 (8) | 0.0009 (7) | 0.0035 (6) | 0.0147 (7) |
O2 | 0.0332 (8) | 0.0832 (13) | 0.0350 (9) | −0.0121 (8) | 0.0051 (6) | 0.0062 (8) |
N1 | 0.0370 (9) | 0.0465 (11) | 0.0267 (9) | −0.0051 (8) | 0.0069 (7) | −0.0036 (8) |
N2 | 0.0307 (9) | 0.0670 (13) | 0.0252 (9) | −0.0038 (8) | 0.0048 (7) | 0.0107 (9) |
C1 | 0.0344 (10) | 0.0371 (11) | 0.0252 (10) | 0.0012 (8) | 0.0047 (8) | −0.0061 (8) |
C2 | 0.0369 (11) | 0.0543 (14) | 0.0347 (12) | 0.0052 (9) | 0.0000 (9) | −0.0030 (11) |
C3 | 0.0322 (11) | 0.0640 (17) | 0.0554 (16) | 0.0028 (11) | −0.0027 (10) | −0.0116 (13) |
C4 | 0.0351 (11) | 0.0569 (15) | 0.0552 (15) | −0.0091 (10) | 0.0156 (10) | −0.0148 (12) |
C5 | 0.0435 (12) | 0.0538 (15) | 0.0348 (12) | −0.0062 (11) | 0.0121 (9) | −0.0047 (11) |
C6 | 0.0359 (11) | 0.0409 (12) | 0.0224 (10) | −0.0012 (9) | 0.0043 (8) | −0.0013 (9) |
O1W | 0.0408 (8) | 0.0687 (11) | 0.0404 (9) | 0.0044 (8) | 0.0068 (7) | 0.0163 (8) |
O1—C6 | 1.234 (2) | C2—C3 | 1.387 (3) |
O2—N2 | 1.387 (2) | C2—H2B | 0.9300 |
O2—H2 | 0.8200 | C3—C4 | 1.367 (3) |
N1—C5 | 1.334 (3) | C3—H3 | 0.9300 |
N1—C1 | 1.344 (3) | C4—C5 | 1.378 (3) |
N2—C6 | 1.325 (2) | C4—H4 | 0.9300 |
N2—H2A | 0.8600 | C5—H5 | 0.9300 |
C1—C2 | 1.382 (3) | O1W—H1WA | 0.8503 |
C1—C6 | 1.496 (3) | O1W—H1WB | 0.8499 |
N2—O2—H2 | 109.5 | C4—C3—H3 | 120.4 |
C5—N1—C1 | 117.26 (17) | C2—C3—H3 | 120.4 |
C6—N2—O2 | 119.60 (16) | C3—C4—C5 | 118.9 (2) |
C6—N2—H2A | 120.2 | C3—C4—H4 | 120.6 |
O2—N2—H2A | 120.2 | C5—C4—H4 | 120.6 |
N1—C1—C2 | 123.08 (19) | N1—C5—C4 | 123.4 (2) |
N1—C1—C6 | 117.54 (16) | N1—C5—H5 | 118.3 |
C2—C1—C6 | 119.38 (18) | C4—C5—H5 | 118.3 |
C1—C2—C3 | 118.2 (2) | O1—C6—N2 | 122.15 (18) |
C1—C2—H2B | 120.9 | O1—C6—C1 | 122.66 (17) |
C3—C2—H2B | 120.9 | N2—C6—C1 | 115.17 (17) |
C4—C3—C2 | 119.2 (2) | H1WA—O1W—H1WB | 102.7 |
C5—N1—C1—C2 | 0.3 (3) | C3—C4—C5—N1 | −1.0 (4) |
C5—N1—C1—C6 | 179.67 (17) | O2—N2—C6—O1 | −0.4 (3) |
N1—C1—C2—C3 | −1.2 (3) | O2—N2—C6—C1 | −178.54 (17) |
C6—C1—C2—C3 | 179.4 (2) | N1—C1—C6—O1 | 175.6 (2) |
C1—C2—C3—C4 | 1.0 (3) | C2—C1—C6—O1 | −5.0 (3) |
C2—C3—C4—C5 | 0.0 (4) | N1—C1—C6—N2 | −6.2 (3) |
C1—N1—C5—C4 | 0.8 (3) | C2—C1—C6—N2 | 173.20 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1W | 0.82 | 1.86 | 2.656 (2) | 163 |
N2—H2A···N1i | 0.86 | 2.31 | 3.010 (2) | 139 |
O1W—H1WA···O1ii | 0.85 | 2.14 | 2.976 (2) | 168 |
O1W—H1WB···O1iii | 0.85 | 1.94 | 2.788 (2) | 173 |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1W | 0.82 | 1.86 | 2.656 (2) | 162.5 |
N2—H2A···N1i | 0.86 | 2.31 | 3.010 (2) | 138.7 |
O1W—H1WA···O1ii | 0.85 | 2.14 | 2.976 (2) | 168.3 |
O1W—H1WB···O1iii | 0.85 | 1.94 | 2.788 (2) | 173.0 |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C6H6N2O2·H2O |
Mr | 156.14 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 18.7471 (13), 3.8129 (4), 20.4813 (17) |
β (°) | 100.570 (7) |
V (Å3) | 1439.2 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.4 × 0.4 × 0.1 |
Data collection | |
Diffractometer | Agilent Xcalibur, Sapphire3 |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2013) |
Tmin, Tmax | 0.476, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2491, 1401, 1053 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.143, 0.99 |
No. of reflections | 1401 |
No. of parameters | 102 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.25 |
Computer programs: CrysAlis PRO (Agilent, 2013), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009).
Acknowledgements
Financial support from the European Community's Seventh Framework Programme (FP7/2007–2013) under grant agreement PIRSES-GA-2013–611488 is gratefully acknowledged. KAO acknowledges for the DAAD fellowship (Leonhard-Euler-Programm).
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