Literature DB >> 22412413

catena-Poly[[(μ-3-hy-droxy-benzoato-κO,O:O)(μ-3-hy-droxy-benzoato-κO,O:O)(isonicotinamide-κN)-lead(II)] monohydrate].

Ibrahim Göker Zaman, Nagihan Caylak Delibaş, Hacali Necefoğlu, Tuncer Hökelek.   

Abstract

In the crystal of the title polymeric compound, {[Pb(C(7)H(5)O(3))(2)(C(6)H(6)N(2)O)]·H(2)O}(n), the Pb(II) ion is chelated by two carboxyl-ate groups of 3-hy-droxy-benzoate (HB) anions, and coordinated by one isonicotinamide mol-ecule; a carboxyl-ate O atom and a hy-droxy O atom from adjacent HB anions bridge the Pb(II) ion to form polymeric chains along [100], in which the Pb(II) ion is in an irregular seven-coordination geometry. The carboxyl-ate groups of the HB ions are slightly twisted away from the attached benzene rings by 2.84 (15) and 4.8 (2)°. The planes of the two benzene rings of the HB ions are oriented with respect to each other at a dihedral angle of 84.41 (8)°. In the crystal, adjacent polymeric chains inter-act via O-H⋯O, N-H⋯O and weak C-H⋯O hydrogen bonds. The solvent water mol-ecule links with the polymeric chains via O-H⋯O hydrogen bonding. π-π stacking between the benzene and pyridine rings and between the benzene rings [centroid-centroid distances = 3.731 (2) and 3.353 (2) Å] are present in the crystal.

Entities:  

Year:  2012        PMID: 22412413      PMCID: PMC3297223          DOI: 10.1107/S1600536812004357

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


Related literature

For niacin, see: Krishnamachari (1974 ▶). For N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Greenaway et al. (1984 ▶); Hökelek & Necefoğlu (1996 ▶); Hökelek, Yılmaz et al. (2009 ▶); Hökelek, Dal et al. (2009a ▶,b ▶,c ▶, 2010 ▶); Hökelek, Süzen et al. (2010 ▶); Hökelek et al. (2011 ▶).

Experimental

Crystal data

[Pb(C7H5O3)2(C6H6N2O)]·H2O M = 621.56 Triclinic, a = 7.3626 (2) Å b = 12.1382 (3) Å c = 12.1789 (3) Å α = 67.165 (2)° β = 74.192 (3)° γ = 88.921 (3)° V = 960.53 (5) Å3 Z = 2 Mo Kα radiation μ = 8.84 mm−1 T = 100 K 0.26 × 0.14 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.395, T max = 0.603 17040 measured reflections 4783 independent reflections 4652 reflections with I > 2σ(I) R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.017 wR(F 2) = 0.050 S = 1.19 4783 reflections 304 parameters 4 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.94 e Å−3 Δρmin = −1.27 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812004357/xu5463sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004357/xu5463Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Pb(C7H5O3)2(C6H6N2O)]·H2OZ = 2
Mr = 621.56F(000) = 596
Triclinic, P1Dx = 2.149 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3626 (2) ÅCell parameters from 9959 reflections
b = 12.1382 (3) Åθ = 2.9–28.5°
c = 12.1789 (3) ŵ = 8.84 mm1
α = 67.165 (2)°T = 100 K
β = 74.192 (3)°Block, yellow
γ = 88.921 (3)°0.26 × 0.14 × 0.13 mm
V = 960.53 (5) Å3
Bruker Kappa APEXII CCD area-detector diffractometer4783 independent reflections
Radiation source: fine-focus sealed tube4652 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 28.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −9→9
Tmin = 0.395, Tmax = 0.603k = −16→16
17040 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.017Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.050H atoms treated by a mixture of independent and constrained refinement
S = 1.19w = 1/[σ2(Fo2) + (0.0228P)2 + 0.6812P] where P = (Fo2 + 2Fc2)/3
4783 reflections(Δ/σ)max = 0.001
304 parametersΔρmax = 0.94 e Å3
4 restraintsΔρmin = −1.27 e Å3
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
Pb10.030913 (12)0.835470 (8)0.138812 (8)0.00786 (4)
O10.1928 (3)0.62307 (19)0.21830 (19)0.0120 (4)
O20.2876 (3)0.79500 (18)0.21917 (19)0.0119 (4)
O30.8367 (3)0.7102 (2)0.40132 (19)0.0124 (4)
H310.765 (6)0.748 (4)0.440 (4)0.024 (10)*
O40.0065 (3)0.98903 (19)0.25722 (19)0.0136 (4)
O50.1523 (3)1.03718 (18)0.05741 (18)0.0110 (4)
O60.0703 (3)1.3836 (2)0.3029 (2)0.0136 (4)
H610.111 (7)1.442 (5)0.294 (5)0.042 (15)*
O70.6149 (3)0.7967 (2)−0.4465 (2)0.0172 (5)
O8−0.1509 (3)0.1982 (2)0.5265 (2)0.0168 (4)
H81−0.066 (6)0.260 (3)0.473 (4)0.057 (16)*
H82−0.127 (8)0.204 (5)0.590 (4)0.062 (17)*
N10.2801 (3)0.8592 (2)−0.0646 (2)0.0106 (5)
N20.7553 (4)0.9791 (3)−0.4941 (2)0.0144 (5)
H210.830 (5)0.981 (4)−0.561 (3)0.039 (13)*
H220.769 (6)1.035 (3)−0.471 (4)0.028 (11)*
C10.3015 (4)0.6828 (3)0.2424 (2)0.0088 (5)
C20.4561 (4)0.6274 (2)0.2976 (2)0.0090 (5)
C30.5721 (4)0.6960 (3)0.3251 (2)0.0093 (5)
H30.55290.77590.30980.011*
C40.7168 (4)0.6450 (3)0.3754 (2)0.0096 (5)
C50.7482 (4)0.5263 (3)0.3954 (2)0.0109 (5)
H50.84810.49310.42620.013*
C60.6310 (4)0.4575 (3)0.3697 (3)0.0112 (5)
H60.65020.37750.38530.013*
C70.4846 (4)0.5077 (3)0.3203 (2)0.0096 (5)
H70.40630.46170.30260.012*
C80.0990 (4)1.0640 (3)0.1532 (3)0.0091 (5)
C90.1525 (4)1.1908 (3)0.1322 (3)0.0091 (5)
C100.0883 (4)1.2299 (3)0.2284 (3)0.0094 (5)
H100.01491.17700.30630.011*
C110.1341 (4)1.3476 (3)0.2076 (3)0.0103 (5)
C120.2455 (5)1.4274 (3)0.0911 (3)0.0178 (6)
H120.27561.50670.07710.021*
C130.3106 (5)1.3867 (3)−0.0033 (3)0.0222 (7)
H130.38561.4392−0.08080.027*
C140.2653 (4)1.2688 (3)0.0164 (3)0.0154 (6)
H140.31011.2422−0.04730.019*
C150.4005 (4)0.9580 (3)−0.1397 (3)0.0118 (5)
H150.40601.0194−0.11280.014*
C160.5163 (4)0.9719 (3)−0.2555 (3)0.0118 (5)
H160.59591.0422−0.30580.014*
C170.5126 (4)0.8796 (3)−0.2960 (3)0.0094 (5)
C180.3894 (4)0.7765 (3)−0.2170 (3)0.0127 (5)
H180.38320.7127−0.24060.015*
C190.2766 (4)0.7705 (3)−0.1032 (3)0.0116 (5)
H190.19460.7016−0.05120.014*
C200.6331 (4)0.8831 (3)−0.4197 (3)0.0110 (5)
U11U22U33U12U13U23
Pb10.00963 (6)0.00600 (6)0.00604 (6)−0.00059 (4)−0.00152 (4)−0.00083 (4)
O10.0153 (9)0.0070 (10)0.0142 (10)−0.0003 (7)−0.0053 (8)−0.0041 (8)
O20.0148 (9)0.0063 (10)0.0158 (10)0.0004 (7)−0.0071 (8)−0.0038 (8)
O30.0131 (9)0.0132 (11)0.0127 (10)−0.0004 (8)−0.0023 (8)−0.0078 (9)
O40.0191 (10)0.0097 (11)0.0091 (9)−0.0018 (8)−0.0011 (8)−0.0024 (8)
O50.0159 (9)0.0092 (10)0.0087 (9)0.0010 (7)−0.0028 (7)−0.0051 (8)
O60.0170 (10)0.0095 (11)0.0140 (10)−0.0022 (8)0.0014 (8)−0.0082 (9)
O70.0193 (10)0.0158 (12)0.0166 (11)−0.0039 (8)0.0024 (8)−0.0113 (9)
O80.0231 (11)0.0151 (12)0.0097 (10)−0.0060 (9)−0.0013 (8)−0.0042 (9)
N10.0095 (10)0.0100 (12)0.0088 (11)0.0013 (9)0.0002 (8)−0.0019 (9)
N20.0185 (12)0.0136 (13)0.0096 (12)−0.0024 (10)0.0021 (9)−0.0071 (10)
C10.0103 (11)0.0079 (13)0.0056 (12)−0.0003 (9)0.0005 (9)−0.0019 (10)
C20.0117 (12)0.0067 (13)0.0059 (12)−0.0004 (9)−0.0002 (9)−0.0013 (10)
C30.0122 (12)0.0058 (13)0.0068 (12)−0.0008 (9)0.0012 (9)−0.0017 (10)
C40.0101 (12)0.0117 (14)0.0047 (11)−0.0016 (10)0.0007 (9)−0.0027 (10)
C50.0124 (12)0.0118 (14)0.0058 (12)0.0014 (10)−0.0003 (9)−0.0023 (11)
C60.0157 (13)0.0072 (13)0.0091 (12)0.0014 (10)−0.0017 (10)−0.0027 (11)
C70.0121 (12)0.0075 (13)0.0083 (12)−0.0011 (10)−0.0011 (9)−0.0033 (10)
C80.0087 (11)0.0084 (13)0.0094 (12)0.0001 (9)−0.0023 (9)−0.0029 (11)
C90.0109 (12)0.0067 (13)0.0088 (12)−0.0001 (9)−0.0031 (10)−0.0020 (10)
C100.0111 (12)0.0063 (13)0.0072 (12)−0.0012 (10)−0.0011 (9)0.0001 (10)
C110.0113 (12)0.0105 (14)0.0102 (13)0.0017 (10)−0.0033 (10)−0.0051 (11)
C120.0259 (15)0.0104 (15)0.0129 (14)−0.0044 (12)−0.0012 (12)−0.0030 (12)
C130.0323 (17)0.0158 (17)0.0103 (14)−0.0101 (13)0.0053 (12)−0.0039 (13)
C140.0206 (14)0.0138 (15)0.0094 (13)−0.0041 (11)−0.0001 (11)−0.0046 (12)
C150.0135 (12)0.0093 (14)0.0128 (13)0.0011 (10)−0.0022 (10)−0.0058 (11)
C160.0112 (12)0.0094 (14)0.0113 (13)−0.0018 (10)−0.0002 (10)−0.0021 (11)
C170.0092 (11)0.0096 (14)0.0087 (12)0.0005 (10)−0.0017 (10)−0.0033 (11)
C180.0132 (12)0.0109 (14)0.0145 (14)0.0007 (10)−0.0020 (10)−0.0069 (12)
C190.0136 (12)0.0068 (13)0.0119 (13)−0.0019 (10)−0.0019 (10)−0.0022 (11)
C200.0113 (12)0.0107 (14)0.0097 (13)0.0004 (10)−0.0014 (10)−0.0037 (11)
Pb1—N12.564 (2)C5—C41.390 (4)
Pb1—O12.753 (2)C5—C61.386 (4)
Pb1—O22.317 (2)C5—H50.9300
Pb1—O3i2.899 (2)C6—H60.9300
Pb1—O42.742 (2)C7—C21.393 (4)
Pb1—O52.344 (2)C7—C61.393 (4)
Pb1—O5ii2.954 (2)C7—H70.9300
O1—C11.253 (3)C9—C141.390 (4)
O2—C11.287 (3)C8—C91.501 (4)
O3—C41.370 (3)C10—C91.394 (4)
O3—H310.86 (4)C10—H100.9300
O4—C81.247 (3)C11—C101.382 (4)
O5—C81.288 (3)C11—C121.397 (4)
O6—C111.361 (3)C12—C131.389 (4)
O6—H610.73 (5)C12—H120.9300
O7—C201.234 (4)C13—C141.387 (4)
O8—H810.89 (2)C13—H130.9300
O8—H820.87 (2)C14—H140.9300
N1—C151.344 (4)C15—H150.9300
N1—C191.334 (4)C16—C151.382 (4)
N2—C201.328 (4)C16—H160.9300
N2—H210.844 (19)C17—C161.391 (4)
N2—H220.843 (19)C17—C181.396 (4)
C1—C21.495 (4)C17—C201.510 (4)
C3—C21.390 (4)C18—H180.9300
C3—C41.390 (4)C19—C181.383 (4)
C3—H30.9300C19—H190.9300
O2—Pb1—O151.00 (6)C2—C7—H7120.2
O2—Pb1—O477.71 (7)C6—C7—H7120.2
O2—Pb1—O585.33 (7)O4—C8—O5121.9 (3)
O2—Pb1—N183.32 (7)O4—C8—C9121.8 (2)
O4—Pb1—O1121.06 (6)O5—C8—C9116.3 (2)
O5—Pb1—O1132.63 (6)C10—C9—C8120.0 (2)
O5—Pb1—O450.94 (6)C14—C9—C8119.6 (2)
O5—Pb1—N177.24 (7)C14—C9—C10120.4 (3)
N1—Pb1—O179.96 (7)C11—C10—C9119.7 (3)
N1—Pb1—O4125.57 (7)C11—C10—H10120.1
C1—O1—Pb183.85 (16)C9—C10—H10120.1
C1—O2—Pb1103.41 (16)O6—C11—C10118.7 (3)
C4—O3—H31105 (3)O6—C11—C12120.8 (3)
C8—O4—Pb184.76 (16)C10—C11—C12120.5 (3)
C8—O5—Pb1102.42 (17)C11—C12—H12120.5
C11—O6—H61116 (4)C13—C12—C11119.1 (3)
H82—O8—H8192 (5)C13—C12—H12120.5
C15—N1—Pb1124.95 (18)C12—C13—H13119.5
C19—N1—Pb1116.64 (18)C14—C13—C12120.9 (3)
C19—N1—C15118.1 (2)C14—C13—H13119.5
C20—N2—H21120 (3)C9—C14—H14120.3
C20—N2—H22120 (3)C13—C14—C9119.3 (3)
H22—N2—H21119 (4)C13—C14—H14120.3
O1—C1—O2121.7 (2)N1—C15—C16122.6 (3)
O1—C1—C2121.4 (2)N1—C15—H15118.7
O2—C1—C2116.9 (2)C16—C15—H15118.7
C3—C2—C1119.8 (2)C15—C16—C17119.3 (3)
C3—C2—C7120.2 (3)C15—C16—H16120.3
C7—C2—C1120.0 (2)C17—C16—H16120.3
C2—C3—H3120.0C16—C17—C18117.9 (2)
C4—C3—C2120.0 (3)C16—C17—C20124.5 (3)
C4—C3—H3120.0C18—C17—C20117.6 (3)
O3—C4—C3121.7 (3)C17—C18—H18120.5
O3—C4—C5118.3 (2)C19—C18—C17119.1 (3)
C3—C4—C5119.9 (3)C19—C18—H18120.5
C4—C5—H5119.9N1—C19—C18123.0 (3)
C6—C5—C4120.1 (3)N1—C19—H19118.5
C6—C5—H5119.9C18—C19—H19118.5
C5—C6—C7120.2 (3)O7—C20—N2123.1 (3)
C5—C6—H6119.9O7—C20—C17118.7 (3)
C7—C6—H6119.9N2—C20—C17118.2 (3)
C2—C7—C6119.6 (3)
O2—Pb1—O1—C10.82 (14)O1—C1—C2—C71.7 (4)
O4—Pb1—O1—C1−35.34 (17)O2—C1—C2—C32.1 (4)
O5—Pb1—O1—C128.21 (18)O2—C1—C2—C7−177.3 (2)
N1—Pb1—O1—C190.32 (16)C4—C3—C2—C7−0.1 (4)
O1—Pb1—O2—C1−0.81 (14)C4—C3—C2—C1−179.5 (2)
O4—Pb1—O2—C1148.04 (17)C2—C3—C4—O3178.6 (2)
O5—Pb1—O2—C1−160.96 (16)C2—C3—C4—C51.6 (4)
N1—Pb1—O2—C1−83.29 (16)C6—C5—C4—O3−179.6 (2)
O1—Pb1—O4—C8122.11 (16)C6—C5—C4—C3−2.4 (4)
O2—Pb1—O4—C894.12 (16)C4—C5—C6—C71.8 (4)
O5—Pb1—O4—C80.14 (15)C6—C7—C2—C1178.8 (2)
N1—Pb1—O4—C821.70 (19)C6—C7—C2—C3−0.6 (4)
O1—Pb1—O5—C8−99.11 (17)C2—C7—C6—C5−0.3 (4)
O2—Pb1—O5—C8−78.09 (16)O4—C8—C9—C10−4.2 (4)
O4—Pb1—O5—C8−0.13 (15)O4—C8—C9—C14176.1 (3)
N1—Pb1—O5—C8−162.28 (17)O5—C8—C9—C10175.1 (2)
O1—Pb1—N1—C15−132.2 (2)O5—C8—C9—C14−4.5 (4)
O1—Pb1—N1—C1954.3 (2)C8—C9—C14—C13178.5 (3)
O2—Pb1—N1—C15−80.7 (2)C10—C9—C14—C13−1.2 (5)
O2—Pb1—N1—C19105.8 (2)C11—C10—C9—C141.3 (4)
O4—Pb1—N1—C15−11.0 (3)C11—C10—C9—C8−178.4 (2)
O4—Pb1—N1—C19175.51 (18)O6—C11—C10—C9−179.8 (2)
O5—Pb1—N1—C156.0 (2)C12—C11—C10—C9−0.5 (4)
O5—Pb1—N1—C19−167.5 (2)O6—C11—C12—C13178.9 (3)
Pb1—O1—C1—O2−1.3 (2)C10—C11—C12—C13−0.4 (5)
Pb1—O1—C1—C2179.7 (2)C11—C12—C13—C140.5 (5)
Pb1—O2—C1—O11.6 (3)C12—C13—C14—C90.3 (5)
Pb1—O2—C1—C2−179.40 (18)C17—C16—C15—N1−1.4 (4)
Pb1—O4—C8—O5−0.2 (2)C18—C17—C16—C150.5 (4)
Pb1—O4—C8—C9179.1 (2)C20—C17—C16—C15−179.4 (3)
Pb1—O5—C8—O40.3 (3)C16—C17—C18—C190.3 (4)
Pb1—O5—C8—C9−179.06 (19)C20—C17—C18—C19−179.8 (3)
Pb1—N1—C15—C16−172.0 (2)C16—C17—C20—O7−178.6 (3)
C19—N1—C15—C161.5 (4)C16—C17—C20—N21.9 (4)
Pb1—N1—C19—C18173.3 (2)C18—C17—C20—O71.5 (4)
C15—N1—C19—C18−0.7 (4)C18—C17—C20—N2−177.9 (3)
O1—C1—C2—C3−178.9 (2)N1—C19—C18—C17−0.2 (4)
D—H···AD—HH···AD···AD—H···A
N2—H21···O4iii0.84 (4)2.21 (4)3.046 (3)175 (4)
N2—H22···O8iv0.85 (4)2.06 (4)2.880 (5)162 (4)
O3—H31···O7v0.86 (5)1.81 (5)2.646 (3)166 (4)
O6—H61···O1vi0.73 (6)2.05 (6)2.755 (4)161 (6)
O8—H81···O6vii0.89 (4)2.02 (4)2.846 (3)154 (4)
O8—H82···O2viii0.87 (5)2.31 (5)3.018 (3)139 (5)
O8—H82···O3ix0.87 (5)2.44 (6)3.054 (3)128 (4)
C12—H12···O1vi0.932.573.269 (4)132
C15—H15···O50.932.463.060 (4)122
C16—H16···O8iv0.932.513.413 (4)165
Table 1

Selected bond lengths (Å)

Pb1—N12.564 (2)
Pb1—O12.753 (2)
Pb1—O22.317 (2)
Pb1—O3i2.899 (2)
Pb1—O42.742 (2)
Pb1—O52.344 (2)
Pb1—O5ii2.954 (2)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
N2—H21⋯O4iii0.84 (4)2.21 (4)3.046 (3)175 (4)
N2—H22⋯O8iv0.85 (4)2.06 (4)2.880 (5)162 (4)
O3—H31⋯O7v0.86 (5)1.81 (5)2.646 (3)166 (4)
O6—H61⋯O1vi0.73 (6)2.05 (6)2.755 (4)161 (6)
O8—H81⋯O6vii0.89 (4)2.02 (4)2.846 (3)154 (4)
O8—H82⋯O2viii0.87 (5)2.31 (5)3.018 (3)139 (5)
O8—H82⋯O3ix0.87 (5)2.44 (6)3.054 (3)128 (4)
C12—H12⋯O1vi0.932.573.269 (4)132
C15—H15⋯O50.932.463.060 (4)122
C16—H16⋯O8iv0.932.513.413 (4)165

Symmetry codes: (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .

  10 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Some aspects of copper metabolism in pellagra.

Authors:  K A Krishnamachari
Journal:  Am J Clin Nutr       Date:  1974-02       Impact factor: 7.045

3.  Aqua-bis(4-formyl-benzoato-κO,O)bis-(isonicotinamide-κN)cadmium(II) monohydrate.

Authors:  Tuncer Hökelek; Filiz Yılmaz; Barış Tercan; Ferdi Gürgen; Hacali Necefoğlu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-23

4.  Diaqua-bis[4-(dimethyl-amino)benzoato-κO](isonicotinamide-κN)manganese(II).

Authors:  Tuncer Hökelek; Hakan Dal; Barış Tercan; Ozgür Aybirdi; Hacali Necefoğlu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-08-08

5.  Diaqua-bis[4-(dimethyl-amino)-benzoato]-κO,O';κO-(isonicotinamide-κN)cobalt(II).

Authors:  Tuncer Hökelek; Hakan Dal; Barış Tercan; Ozgür Aybirdi; Hacali Necefoğlu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-14

6.  Bis[μ-4-(dimethyl-amino)-benzoato]-κO,O':O;κO:O,O'-bis-{aqua-[4-(dimethyl-amino)-benzoato-κO,O'](nicotinamide-κN)cadmium(II)}.

Authors:  Tuncer Hökelek; Yasemin Süzen; Barış Tercan; Ozgür Aybirdi; Hacali Necefoğlu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-16

7.  catena-Poly[[bis-(4-methyl-benzoato-κO:O')lead(II)]-μ-nicotinamide-κN:O].

Authors:  Tuncer Hökelek; Hakan Dal; Barış Tercan; Efdal Cimen; Hacali Necefoğlu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-17

8.  Bis(isonicotinamide-κN)bis-[4-(methyl-amino)benzoato]zinc(II) monohydrate.

Authors:  Tuncer Hökelek; Hakan Dal; Barış Tercan; Ozgür Aybirdi; Hacali Necefoğlu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-17

9.  catena-Poly[[[bis-(4-ethyl-benzoato-κO,O')lead(II)]-μ-nicotinamide-κN:O] monohydrate].

Authors:  Tuncer Hökelek; Barış Tercan; Ertan Sahin; Vedat Aktaş; Hacali Necefoğlu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-09

10.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  10 in total
  3 in total

1.  catena-Poly[[aqua-(2-iodo-benzoato-κO)cobalt(II)]-μ-aqua-μ-2-iodo-benzoato-κ(2)O:O'].

Authors:  Omür Aydın; Nagihan Caylak Delibaş; Hacali Necefoğlu; Tuncer Hökelek
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-18

2.  Crystal structure of catena-poly[[[di-aqua-bis-(2,4,6-tri-methyl-benzoato-κO)cobalt(II)]-μ-aqua-κ2O:O] dihydrate].

Authors:  Tuncer Hökelek; Nurcan Akduran; Safiye Özkaya; Hacali Necefoğlu
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2017-04-13

3.  catena-Poly[aqua-bis-(μ-3-chloro-benzo-ato-κ(2) O:O')zinc].

Authors:  Nihat Bozkurt; Nefise Dilek; Nagihan Caylak Delibaş; Hacali Necefoğlu; Tuncer Hökelek
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-06-15
  3 in total

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