Literature DB >> 21754593

Aqua-(di-2-pyridyl-amine-κN,N)(pyridine-2,6-dicarboxyl-ato-κO,N,O)zinc monohydrate.

Figen Durkaya, Necmi Dege, Güneş Demirtaş, Ibrahim Uçar.   

Abstract

In the title compound, [Zn(C(7)H(3)NO(4))(C(10)H(9)N(3))(H(2)O)]·H(2)O, the Zn(II) atom has a distorted octa-hedral coordination geometry. One of the water mol-ecules is coordinated with the Zn(II) ion and this mol-ecule forms an O-H⋯O inter-action with the lattice water mol-ecule. The pyridine-2,6-dicarboxyl-ate ligand is almost planar (r.m.s. deviation = 0.0242 Å). In the crystal, C-H⋯O, C-H⋯N, O-H⋯O and N-H⋯O hydrogen bonds are present.

Entities:  

Year:  2011        PMID： 21754593      PMCID： PMC3120453          DOI： 10.1107/S1600536811015571

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the biological activity of 2,6-pyridine­dicarb­oxy­lic acid, see: Chung et al. (1971 ▶); Tang et al. (1968 ▶). For the crystal structures of pyridine-2,6-dicarboxyl­ate derivatives, see: Uçar et al. (2007a ▶,b ▶); Uçar et al. (2009 ▶); Cui et al. (2011 ▶). For C—H⋯O inter­actions, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

[Zn(C7H3NO4)(C10H9N3)(H2O)]·H2O M = 437.71 Triclinic, a = 6.8349 (5) Å b = 11.1246 (8) Å c = 12.1910 (9) Å α = 96.109 (6)° β = 96.404 (6)° γ = 107.381 (6)° V = 869.51 (11) Å3 Z = 2 Mo Kα radiation μ = 1.46 mm−1 T = 296 K 0.44 × 0.27 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.598, T max = 0.833 7786 measured reflections 3398 independent reflections 3093 reflections with I > 2σ(I) R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.071 S = 1.05 3398 reflections 315 parameters 3 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.36 e Å−3 Δρmin = −0.51 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015571/zj2009sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015571/zj2009Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Zn(C7H3NO4)(C10H9N3)(H2O)]·H2OZ = 2
Mr = 437.71F(000) = 448
Triclinic, P1Dx = 1.672 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8349 (5) ÅCell parameters from 18443 reflections
b = 11.1246 (8) Åθ = 2.4–27.4°
c = 12.1910 (9) ŵ = 1.46 mm−1
α = 96.109 (6)°T = 296 K
β = 96.404 (6)°Prism, colorless
γ = 107.381 (6)°0.44 × 0.27 × 0.13 mm
V = 869.51 (11) Å3
Stoe IPDS 2 diffractometer3398 independent reflections
Radiation source: fine-focus sealed tube3093 reflections with I > 2σ(I)
graphiteRint = 0.019
w–scan rotationθmax = 26.0°, θmin = 2.4°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)h = −8→8
Tmin = 0.598, Tmax = 0.833k = −13→13
7786 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0354P)2 + 0.4854P] where P = (Fo2 + 2Fc2)/3
3398 reflections(Δ/σ)max = 0.001
315 parametersΔρmax = 0.36 e Å−3
3 restraintsΔρmin = −0.51 e Å−3
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.
xyzUiso*/Ueq
C10.8321 (4)0.6257 (2)0.2034 (2)0.0405 (5)
C20.9281 (4)0.7536 (2)0.2147 (2)0.0457 (5)
C31.0007 (4)0.8203 (2)0.3211 (2)0.0448 (5)
C40.9665 (3)0.7576 (2)0.4108 (2)0.0384 (5)
C50.8625 (3)0.62585 (18)0.39379 (17)0.0305 (4)
C60.7053 (3)0.45086 (19)0.50443 (17)0.0301 (4)
C70.6890 (3)0.4313 (2)0.61532 (19)0.0371 (5)
C80.5781 (4)0.3143 (2)0.6365 (2)0.0428 (5)
C90.4779 (4)0.2187 (2)0.5475 (2)0.0457 (5)
C100.4947 (4)0.2455 (2)0.4423 (2)0.0421 (5)
C110.8865 (3)0.1646 (2)0.28574 (18)0.0373 (5)
C120.6742 (3)0.10009 (19)0.21539 (17)0.0318 (4)
C130.5899 (4)−0.0290 (2)0.1784 (2)0.0404 (5)
C140.3928 (4)−0.0736 (2)0.1172 (2)0.0451 (6)
C150.2853 (3)0.0102 (2)0.0934 (2)0.0400 (5)
C160.3784 (3)0.13814 (19)0.13253 (16)0.0315 (4)
C170.2853 (3)0.2443 (2)0.11450 (17)0.0353 (4)
N10.6108 (3)0.35941 (16)0.41824 (15)0.0340 (4)
N20.8254 (3)0.56958 (17)0.48748 (16)0.0328 (4)
N30.8026 (3)0.55946 (16)0.29092 (14)0.0319 (4)
N40.5679 (3)0.17928 (15)0.19219 (14)0.0301 (3)
O10.4027 (2)0.35555 (15)0.15426 (14)0.0452 (4)
O20.1071 (2)0.21538 (16)0.06327 (14)0.0456 (4)
O30.9333 (2)0.28411 (14)0.31253 (12)0.0360 (3)
O40.9925 (3)0.09778 (17)0.31240 (19)0.0629 (6)
O50.8755 (3)0.38070 (19)0.10477 (16)0.0480 (4)
O60.7196 (4)0.4353 (2)−0.0951 (2)0.0736 (6)
Zn10.69556 (4)0.36631 (2)0.25541 (2)0.03462 (9)
H6A0.598 (3)0.411 (2)−0.062 (2)0.052*
H6B0.727 (4)0.5068 (19)−0.118 (2)0.052*
H10.788 (4)0.577 (3)0.131 (2)0.046 (7)*
H20.937 (4)0.790 (3)0.149 (2)0.054 (8)*
H31.064 (4)0.901 (3)0.331 (2)0.051 (8)*
H41.005 (4)0.797 (2)0.483 (2)0.039 (6)*
H50.881 (4)0.612 (2)0.540 (2)0.032 (6)*
H5A0.941 (5)0.329 (3)0.094 (3)0.060 (9)*
H5B0.818 (6)0.384 (3)0.043 (3)0.077 (11)*
H70.754 (4)0.499 (3)0.672 (2)0.045 (7)*
H80.567 (4)0.299 (3)0.709 (2)0.046 (7)*
H90.391 (5)0.139 (3)0.558 (2)0.059 (8)*
H100.427 (4)0.185 (3)0.380 (2)0.047 (7)*
H130.661 (4)−0.083 (3)0.195 (2)0.052 (8)*
H140.336 (4)−0.159 (3)0.092 (2)0.053 (8)*
H150.160 (5)−0.016 (3)0.055 (2)0.058 (8)*
U11U22U33U12U13U23
C10.0449 (12)0.0410 (12)0.0389 (12)0.0179 (10)0.0067 (9)0.0071 (10)
C20.0487 (13)0.0418 (13)0.0538 (14)0.0191 (11)0.0142 (11)0.0175 (11)
C30.0397 (12)0.0277 (11)0.0670 (16)0.0088 (9)0.0094 (11)0.0105 (11)
C40.0347 (11)0.0291 (10)0.0480 (13)0.0097 (8)−0.0003 (9)−0.0016 (9)
C50.0232 (9)0.0277 (10)0.0405 (11)0.0108 (7)−0.0005 (8)0.0015 (8)
C60.0235 (9)0.0304 (10)0.0367 (10)0.0116 (8)−0.0002 (8)0.0020 (8)
C70.0329 (10)0.0413 (12)0.0373 (11)0.0142 (9)0.0016 (9)0.0032 (9)
C80.0398 (12)0.0497 (14)0.0442 (13)0.0184 (10)0.0102 (10)0.0136 (11)
C90.0403 (12)0.0372 (12)0.0614 (15)0.0101 (10)0.0162 (11)0.0119 (11)
C100.0381 (12)0.0329 (11)0.0493 (13)0.0046 (9)0.0074 (10)−0.0011 (10)
C110.0351 (11)0.0342 (11)0.0404 (11)0.0128 (9)−0.0054 (9)0.0014 (9)
C120.0320 (10)0.0295 (10)0.0327 (10)0.0106 (8)0.0003 (8)0.0011 (8)
C130.0405 (12)0.0298 (11)0.0490 (13)0.0121 (9)0.0000 (10)0.0024 (9)
C140.0428 (12)0.0269 (11)0.0560 (14)0.0028 (9)0.0006 (11)−0.0049 (10)
C150.0304 (11)0.0361 (11)0.0440 (12)0.0029 (9)−0.0040 (9)−0.0027 (9)
C160.0277 (9)0.0326 (10)0.0299 (10)0.0064 (8)−0.0008 (8)0.0002 (8)
C170.0310 (10)0.0376 (11)0.0344 (10)0.0106 (9)−0.0033 (8)0.0009 (9)
N10.0306 (8)0.0285 (8)0.0397 (9)0.0070 (7)0.0025 (7)0.0006 (7)
N20.0327 (9)0.0276 (9)0.0322 (9)0.0067 (7)−0.0051 (7)−0.0022 (7)
N30.0318 (8)0.0286 (8)0.0350 (9)0.0106 (7)0.0016 (7)0.0031 (7)
N40.0294 (8)0.0277 (8)0.0300 (8)0.0078 (7)−0.0021 (6)−0.0001 (7)
O10.0388 (8)0.0328 (8)0.0579 (10)0.0125 (7)−0.0144 (7)−0.0006 (7)
O20.0343 (8)0.0477 (9)0.0491 (9)0.0145 (7)−0.0125 (7)−0.0026 (7)
O30.0324 (7)0.0308 (7)0.0396 (8)0.0092 (6)−0.0078 (6)−0.0010 (6)
O40.0539 (11)0.0424 (10)0.0875 (14)0.0246 (8)−0.0250 (10)−0.0019 (9)
O50.0541 (10)0.0532 (11)0.0450 (10)0.0274 (9)0.0081 (8)0.0114 (8)
O60.0919 (17)0.0610 (13)0.0670 (14)0.0290 (12)−0.0116 (12)0.0154 (11)
Zn10.03612 (14)0.02497 (13)0.03752 (15)0.00839 (9)−0.00719 (10)−0.00130 (9)
C1—N31.360 (3)C11—C121.525 (3)
C1—C21.362 (3)C12—N41.332 (3)
C1—H10.95 (3)C12—C131.381 (3)
C2—C31.382 (4)C13—C141.384 (3)
C2—H20.94 (3)C13—H130.90 (3)
C3—C41.363 (4)C14—C151.383 (3)
C3—H30.86 (3)C14—H140.91 (3)
C4—C51.406 (3)C15—C161.380 (3)
C4—H40.92 (3)C15—H150.88 (3)
C5—N31.339 (3)C16—N41.334 (2)
C5—N21.372 (3)C16—C171.523 (3)
C6—N11.336 (3)C17—O21.237 (2)
C6—N21.382 (3)C17—O11.266 (3)
C6—C71.403 (3)N1—Zn12.1318 (18)
C7—C81.364 (3)N2—H50.75 (3)
C7—H70.93 (3)N3—Zn12.0327 (17)
C8—C91.389 (4)N4—Zn12.0269 (16)
C8—H80.93 (3)O1—Zn12.1947 (15)
C9—C101.357 (4)O3—Zn12.1755 (14)
C9—H90.94 (3)O5—Zn12.3148 (19)
C10—N11.361 (3)O5—H5A0.83 (4)
C10—H100.93 (3)O5—H5B0.82 (4)
C11—O41.226 (3)O6—H6A0.944 (16)
C11—O31.268 (3)O6—H6B0.860 (17)
N3—C1—C2123.8 (2)C16—C15—C14118.5 (2)
N3—C1—H1116.2 (16)C16—C15—H15120 (2)
C2—C1—H1119.9 (16)C14—C15—H15121.7 (19)
C1—C2—C3118.3 (2)N4—C16—C15120.37 (19)
C1—C2—H2116.5 (18)N4—C16—C17113.52 (17)
C3—C2—H2125.2 (18)C15—C16—C17126.11 (18)
C4—C3—C2119.4 (2)O2—C17—O1126.4 (2)
C4—C3—H3120.3 (19)O2—C17—C16118.48 (19)
C2—C3—H3120.4 (19)O1—C17—C16115.11 (17)
C3—C4—C5119.7 (2)C6—N1—C10117.04 (19)
C3—C4—H4123.9 (16)C6—N1—Zn1122.80 (14)
C5—C4—H4116.5 (16)C10—N1—Zn1118.08 (15)
N3—C5—N2122.07 (18)C5—N2—C6133.38 (18)
N3—C5—C4121.2 (2)C5—N2—H5113.4 (19)
N2—C5—C4116.70 (19)C6—N2—H5113.2 (19)
N1—C6—N2120.82 (19)C5—N3—C1117.46 (18)
N1—C6—C7122.11 (19)C5—N3—Zn1125.03 (14)
N2—C6—C7117.06 (18)C1—N3—Zn1117.26 (15)
C8—C7—C6119.2 (2)C12—N4—C16121.92 (17)
C8—C7—H7122.3 (16)C12—N4—Zn1118.39 (13)
C6—C7—H7118.4 (16)C16—N4—Zn1119.64 (14)
C7—C8—C9119.1 (2)C17—O1—Zn1115.49 (13)
C7—C8—H8120.6 (17)C11—O3—Zn1115.28 (12)
C9—C8—H8120.2 (17)Zn1—O5—H5A117 (2)
C10—C9—C8118.5 (2)Zn1—O5—H5B120 (3)
C10—C9—H9119.6 (18)H5A—O5—H5B106 (3)
C8—C9—H9121.8 (18)H6A—O6—H6B107 (2)
C9—C10—N1123.9 (2)N4—Zn1—N3169.48 (7)
C9—C10—H10121.3 (17)N4—Zn1—N198.90 (7)
N1—C10—H10114.8 (17)N3—Zn1—N189.01 (7)
O4—C11—O3126.5 (2)N4—Zn1—O376.80 (6)
O4—C11—C12118.25 (19)N3—Zn1—O3110.79 (6)
O3—C11—C12115.21 (18)N1—Zn1—O386.62 (6)
N4—C12—C13120.53 (18)N4—Zn1—O175.75 (6)
N4—C12—C11114.27 (17)N3—Zn1—O195.92 (6)
C13—C12—C11125.19 (19)N1—Zn1—O1101.92 (7)
C12—C13—C14118.4 (2)O3—Zn1—O1152.19 (6)
C12—C13—H13120.5 (18)N4—Zn1—O585.73 (7)
C14—C13—H13121.1 (18)N3—Zn1—O588.44 (7)
C15—C14—C13120.2 (2)N1—Zn1—O5164.45 (7)
C15—C14—H14120.7 (18)O3—Zn1—O579.96 (7)
C13—C14—H14119.1 (18)O1—Zn1—O593.61 (7)
N3—C1—C2—C30.3 (4)C15—C16—N4—Zn1−176.87 (16)
C1—C2—C3—C4−2.7 (4)C17—C16—N4—Zn13.2 (2)
C2—C3—C4—C51.4 (3)O2—C17—O1—Zn1173.65 (19)
C3—C4—C5—N32.5 (3)C16—C17—O1—Zn1−6.8 (2)
C3—C4—C5—N2−177.3 (2)O4—C11—O3—Zn1−176.9 (2)
N1—C6—C7—C81.9 (3)C12—C11—O3—Zn11.7 (2)
N2—C6—C7—C8−177.71 (19)C12—N4—Zn1—N3139.2 (3)
C6—C7—C8—C9−2.3 (3)C16—N4—Zn1—N3−43.2 (4)
C7—C8—C9—C100.2 (4)C12—N4—Zn1—N1−82.39 (16)
C8—C9—C10—N12.5 (4)C16—N4—Zn1—N195.14 (16)
O4—C11—C12—N4178.7 (2)C12—N4—Zn1—O31.98 (15)
O3—C11—C12—N40.0 (3)C16—N4—Zn1—O3179.51 (16)
O4—C11—C12—C13−0.1 (4)C12—N4—Zn1—O1177.47 (17)
O3—C11—C12—C13−178.9 (2)C16—N4—Zn1—O1−4.99 (15)
N4—C12—C13—C14−0.2 (3)C12—N4—Zn1—O582.65 (16)
C11—C12—C13—C14178.5 (2)C16—N4—Zn1—O5−99.81 (16)
C12—C13—C14—C150.5 (4)C5—N3—Zn1—N4162.2 (3)
C13—C14—C15—C16−0.3 (4)C1—N3—Zn1—N4−23.7 (5)
C14—C15—C16—N4−0.2 (3)C5—N3—Zn1—N123.17 (16)
C14—C15—C16—C17179.7 (2)C1—N3—Zn1—N1−162.73 (16)
N4—C16—C17—O2−177.65 (19)C5—N3—Zn1—O3−62.84 (17)
C15—C16—C17—O22.4 (3)C1—N3—Zn1—O3111.27 (16)
N4—C16—C17—O12.7 (3)C5—N3—Zn1—O1125.05 (16)
C15—C16—C17—O1−177.2 (2)C1—N3—Zn1—O1−60.85 (16)
N2—C6—N1—C10−179.72 (19)C5—N3—Zn1—O5−141.49 (16)
C7—C6—N1—C100.7 (3)C1—N3—Zn1—O532.62 (16)
N2—C6—N1—Zn117.0 (3)C6—N1—Zn1—N4160.71 (15)
C7—C6—N1—Zn1−162.58 (15)C10—N1—Zn1—N4−2.40 (17)
C9—C10—N1—C6−3.0 (3)C6—N1—Zn1—N3−26.25 (16)
C9—C10—N1—Zn1161.11 (19)C10—N1—Zn1—N3170.64 (17)
N3—C5—N2—C6−10.9 (3)C6—N1—Zn1—O384.64 (16)
C4—C5—N2—C6168.9 (2)C10—N1—Zn1—O3−78.47 (16)
N1—C6—N2—C56.7 (3)C6—N1—Zn1—O1−122.10 (16)
C7—C6—N2—C5−173.7 (2)C10—N1—Zn1—O174.79 (17)
N2—C5—N3—C1174.93 (19)C6—N1—Zn1—O554.4 (3)
C4—C5—N3—C1−4.8 (3)C10—N1—Zn1—O5−108.8 (3)
N2—C5—N3—Zn1−11.0 (3)C11—O3—Zn1—N4−1.98 (15)
C4—C5—N3—Zn1169.25 (15)C11—O3—Zn1—N3−174.37 (15)
C2—C1—N3—C53.6 (3)C11—O3—Zn1—N197.98 (16)
C2—C1—N3—Zn1−171.01 (19)C11—O3—Zn1—O1−11.4 (2)
C13—C12—N4—C16−0.4 (3)C11—O3—Zn1—O5−89.92 (16)
C11—C12—N4—C16−179.23 (18)C17—O1—Zn1—N46.50 (16)
C13—C12—N4—Zn1177.11 (17)C17—O1—Zn1—N3179.98 (17)
C11—C12—N4—Zn1−1.8 (2)C17—O1—Zn1—N1−89.78 (17)
C15—C16—N4—C120.6 (3)C17—O1—Zn1—O315.9 (3)
C17—C16—N4—C12−179.36 (18)C17—O1—Zn1—O591.17 (17)
D—H···AD—HH···AD···AD—H···A
C10—H10···N40.93 (3)2.59 (3)3.189 (3)123 (2)
O5—H5B···O60.82 (4)1.95 (4)2.750 (3)166 (4)
N2—H5···O3i0.75 (3)2.08 (3)2.823 (2)172 (3)
O6—H6B···O1ii0.86 (2)2.05 (2)2.832 (3)151 (2)
O5—H5A···O2iii0.83 (4)1.97 (4)2.804 (3)176 (3)
C2—H2···O2ii0.94 (3)2.56 (3)3.432 (3)155 (2)
C3—H3···O4iv0.86 (3)2.41 (3)3.117 (3)140 (2)
C15—H15···O2v0.88 (3)2.57 (3)3.309 (3)142 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C10—H10⋯N40.93 (3)2.59 (3)3.189 (3)123 (2)
O5—H5B⋯O60.82 (4)1.95 (4)2.750 (3)166 (4)
N2—H5⋯O3i0.75 (3)2.08 (3)2.823 (2)172 (3)
O6—H6B⋯O1ii0.86 (2)2.05 (2)2.832 (3)151 (2)
O5—H5A⋯O2iii0.83 (4)1.97 (4)2.804 (3)176 (3)
C2—H2⋯O2ii0.94 (3)2.56 (3)3.432 (3)155 (2)
C3—H3⋯O4iv0.86 (3)2.41 (3)3.117 (3)140 (2)
C15—H15⋯O2v0.88 (3)2.57 (3)3.309 (3)142 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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