Literature DB >> 22090919

Diaqua-bis-(N,N'-diethyl-nicotinamide-κN)bis-(4-fluoro-benzoato-κO)copper(II).

Hacali Necefoğlu, Füreya Elif Ozbek, Vijdan Oztürk, Vedat Adıgüzel, Tuncer Hökelek.   

Abstract

The asymmetric unit of the title mononuclear Cu(II) complex, [Cu(C(7)H(4)FO(2))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], contains one-half of the mol-ecule. The Cu(II) ion is located on an inversion centre, and is coordinated by two N atoms from two diethyl-nicotinamide ligands, two O atoms from two 4-fluoro-benzoate (PFB) ligands and two water mol-ecules in a distorted octa-hedral geometry. In the PFB ligand, the carboxyl-ate group is twisted at an angle of 2.10 (14)° from the attached benzene ring. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link mol-ecules related by translation along the a axis into chains. Weak inter-molecular C-H⋯O hydrogen bonds and π-π inter-actions between the pyridine rings of neighbouring mol-ecules [centroid-to-centroid distance = 3.571 (2) Å] further consolidate the crystal packing.

Entities:  

Year:  2011        PMID： 22090919      PMCID： PMC3212262          DOI： 10.1107/S1600536811029941

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


Related literature

For background to niacin, see: Krishnamachari (1974 ▶). For infomation on the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek et al. (1996 ▶, 2009a ▶,b ▶); Hökelek & Necefoğlu (1998 ▶, 2007 ▶); Necefoğlu et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Cu(C7H4FO2)2(C10H14N2O)2(H2O)2] M = 734.25 Triclinic, a = 7.4802 (2) Å b = 8.6753 (2) Å c = 14.6695 (4) Å α = 77.164 (3)° β = 84.723 (4)° γ = 65.151 (2)° V = 842.23 (4) Å3 Z = 1 Mo Kα radiation μ = 0.72 mm−1 T = 100 K 0.48 × 0.32 × 0.21 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.759, T max = 0.860 13620 measured reflections 4109 independent reflections 3714 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.099 S = 1.15 4109 reflections 233 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.57 e Å−3 Δρmin = −0.45 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/S1600536811029941/cv6646sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029941/cv6646Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cu(C7H4FO2)2(C10H14N2O)2(H2O)2]Z = 1
Mr = 734.25F(000) = 383
Triclinic, P1Dx = 1.448 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4802 (2) ÅCell parameters from 9044 reflections
b = 8.6753 (2) Åθ = 2.9–28.4°
c = 14.6695 (4) ŵ = 0.72 mm−1
α = 77.164 (3)°T = 100 K
β = 84.723 (4)°Block, blue
γ = 65.151 (2)°0.48 × 0.32 × 0.21 mm
V = 842.23 (4) Å3
Bruker Kappa APEXII CCD area-detector diffractometer4109 independent reflections
Radiation source: fine-focus sealed tube3714 reflections with I > 2σ(I)
graphiteRint = 0.025
φ and ω scansθmax = 28.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −9→9
Tmin = 0.759, Tmax = 0.860k = −11→11
13620 measured reflectionsl = −19→19
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.15w = 1/[σ2(Fo2) + (0.0524P)2 + 0.2704P] where P = (Fo2 + 2Fc2)/3
4109 reflections(Δ/σ)max < 0.001
233 parametersΔρmax = 0.57 e Å−3
2 restraintsΔρmin = −0.45 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
Cu10.00000.00000.00000.01357 (9)
O10.16849 (16)−0.15368 (15)0.10899 (8)0.0158 (2)
O2−0.04849 (17)−0.19328 (17)0.21759 (8)0.0203 (3)
O3−0.43885 (17)−0.29279 (17)−0.12427 (8)0.0201 (3)
O40.29700 (18)0.01961 (18)−0.07056 (9)0.0209 (3)
H410.242 (4)0.068 (3)−0.1223 (13)0.047 (8)*
H420.382 (3)−0.074 (2)−0.0817 (16)0.032 (6)*
N10.03309 (19)−0.20678 (18)−0.05247 (9)0.0140 (3)
N2−0.2966 (2)−0.34165 (19)−0.26337 (10)0.0170 (3)
F10.65236 (17)−0.32105 (18)0.47171 (7)0.0329 (3)
C10.1133 (2)−0.1884 (2)0.19273 (11)0.0144 (3)
C20.2588 (2)−0.2244 (2)0.26753 (11)0.0149 (3)
C30.2080 (2)−0.2568 (2)0.36158 (11)0.0177 (3)
H30.0846−0.25640.37770.021*
C40.3405 (3)−0.2895 (2)0.43123 (12)0.0209 (4)
H40.3080−0.31100.49410.025*
C50.5214 (3)−0.2892 (2)0.40410 (12)0.0212 (4)
C60.5773 (2)−0.2567 (2)0.31234 (12)0.0197 (3)
H60.7008−0.25680.29700.024*
C70.4429 (2)−0.2236 (2)0.24351 (11)0.0159 (3)
H70.4761−0.20060.18080.019*
C80.2015 (2)−0.3509 (2)−0.04352 (11)0.0158 (3)
H80.3068−0.3555−0.01220.019*
C90.2241 (2)−0.4928 (2)−0.07912 (11)0.0170 (3)
H90.3423−0.5912−0.07110.020*
C100.0693 (2)−0.4873 (2)−0.12681 (11)0.0159 (3)
H100.0819−0.5808−0.15190.019*
C11−0.1058 (2)−0.3376 (2)−0.13609 (10)0.0141 (3)
C12−0.1186 (2)−0.2029 (2)−0.09675 (11)0.0141 (3)
H12−0.2374−0.1052−0.10110.017*
C13−0.2925 (2)−0.3226 (2)−0.17555 (11)0.0148 (3)
C14−0.1364 (3)−0.3544 (3)−0.33111 (12)0.0215 (4)
H14A−0.1352−0.4266−0.37320.026*
H14B−0.0117−0.4107−0.29790.026*
C15−0.1552 (3)−0.1797 (3)−0.38791 (16)0.0354 (5)
H15A−0.0445−0.1953−0.42930.053*
H15B−0.1584−0.1069−0.34660.053*
H15C−0.2747−0.1262−0.42390.053*
C16−0.4830 (2)−0.3304 (2)−0.29629 (13)0.0211 (4)
H16A−0.5377−0.3920−0.24650.025*
H16B−0.4550−0.3885−0.34860.025*
C17−0.6367 (3)−0.1461 (3)−0.32646 (15)0.0288 (4)
H17A−0.7545−0.1488−0.34550.043*
H17B−0.5866−0.0855−0.37780.043*
H17C−0.6660−0.0874−0.27510.043*
U11U22U33U12U13U23
Cu10.01438 (14)0.01390 (16)0.01479 (14)−0.00694 (11)−0.00242 (9)−0.00428 (10)
O10.0159 (5)0.0163 (6)0.0160 (5)−0.0067 (5)−0.0017 (4)−0.0041 (4)
O20.0151 (6)0.0250 (7)0.0224 (6)−0.0102 (5)−0.0015 (4)−0.0035 (5)
O30.0144 (5)0.0262 (7)0.0218 (6)−0.0087 (5)0.0012 (4)−0.0092 (5)
O40.0163 (6)0.0227 (7)0.0216 (6)−0.0052 (5)0.0000 (5)−0.0063 (5)
N10.0131 (6)0.0153 (7)0.0159 (6)−0.0077 (5)0.0011 (5)−0.0044 (5)
N20.0141 (6)0.0198 (7)0.0189 (6)−0.0069 (5)−0.0020 (5)−0.0063 (5)
F10.0312 (6)0.0496 (8)0.0231 (5)−0.0225 (6)−0.0122 (4)−0.0007 (5)
C10.0147 (7)0.0100 (7)0.0197 (7)−0.0047 (6)−0.0021 (6)−0.0052 (6)
C20.0156 (7)0.0122 (8)0.0176 (7)−0.0056 (6)−0.0011 (6)−0.0045 (6)
C30.0167 (7)0.0172 (8)0.0206 (8)−0.0080 (6)0.0000 (6)−0.0047 (6)
C40.0250 (9)0.0235 (9)0.0157 (7)−0.0116 (7)−0.0011 (6)−0.0029 (7)
C50.0227 (8)0.0231 (9)0.0204 (8)−0.0109 (7)−0.0082 (6)−0.0033 (7)
C60.0160 (8)0.0209 (9)0.0240 (8)−0.0091 (7)−0.0024 (6)−0.0039 (7)
C70.0170 (7)0.0148 (8)0.0168 (7)−0.0073 (6)−0.0007 (6)−0.0034 (6)
C80.0135 (7)0.0177 (8)0.0166 (7)−0.0064 (6)−0.0002 (5)−0.0044 (6)
C90.0129 (7)0.0174 (8)0.0193 (7)−0.0041 (6)−0.0006 (6)−0.0051 (6)
C100.0164 (7)0.0144 (8)0.0183 (7)−0.0064 (6)0.0011 (6)−0.0065 (6)
C110.0141 (7)0.0158 (8)0.0149 (7)−0.0082 (6)−0.0002 (5)−0.0037 (6)
C120.0126 (7)0.0143 (8)0.0162 (7)−0.0059 (6)−0.0008 (5)−0.0036 (6)
C130.0145 (7)0.0121 (8)0.0188 (7)−0.0055 (6)−0.0020 (6)−0.0037 (6)
C140.0196 (8)0.0264 (10)0.0183 (8)−0.0075 (7)0.0001 (6)−0.0081 (7)
C150.0334 (11)0.0348 (12)0.0418 (11)−0.0194 (9)0.0083 (9)−0.0077 (10)
C160.0186 (8)0.0229 (9)0.0255 (8)−0.0082 (7)−0.0068 (6)−0.0099 (7)
C170.0203 (9)0.0243 (10)0.0397 (10)−0.0036 (7)−0.0097 (7)−0.0097 (8)
Cu1—O11.9833 (11)C6—H60.9300
Cu1—O1i1.9833 (11)C7—C61.388 (2)
Cu1—O42.4192 (12)C7—H70.9300
Cu1—O4i2.4192 (12)C8—H80.9300
Cu1—N12.0192 (14)C9—C81.382 (2)
Cu1—N1i2.0192 (14)C9—C101.385 (2)
O1—C11.2716 (19)C9—H90.9300
O2—C11.247 (2)C10—H100.9300
O3—C131.2363 (19)C11—C101.395 (2)
O4—H410.831 (17)C11—C131.505 (2)
O4—H420.833 (16)C12—C111.379 (2)
N1—C81.342 (2)C12—H120.9300
N1—C121.343 (2)C14—C151.514 (3)
N2—C131.339 (2)C14—H14A0.9700
N2—C141.467 (2)C14—H14B0.9700
N2—C161.475 (2)C15—H15A0.9600
F1—C51.3601 (19)C15—H15B0.9600
C1—C21.505 (2)C15—H15C0.9600
C2—C31.395 (2)C16—C171.519 (3)
C2—C71.393 (2)C16—H16A0.9700
C3—C41.388 (2)C16—H16B0.9700
C3—H30.9300C17—H17A0.9600
C4—C51.376 (3)C17—H17B0.9600
C4—H40.9300C17—H17C0.9600
C6—C51.376 (2)
O1—Cu1—O1i180.00 (9)C6—C7—C2120.55 (15)
O1—Cu1—O485.97 (4)C6—C7—H7119.7
O1i—Cu1—O494.03 (4)N1—C8—C9122.39 (15)
O1—Cu1—O4i94.03 (4)N1—C8—H8118.8
O1i—Cu1—O4i85.97 (4)C9—C8—H8118.8
O4i—Cu1—O4180.00 (9)C8—C9—C10119.52 (15)
N1—Cu1—O494.85 (5)C8—C9—H9120.2
N1i—Cu1—O485.15 (5)C10—C9—H9120.2
N1—Cu1—O4i85.15 (5)C9—C10—C11118.13 (16)
N1i—Cu1—O4i94.85 (5)C9—C10—H10120.9
O1—Cu1—N191.11 (5)C11—C10—H10120.9
O1i—Cu1—N188.89 (5)C10—C11—C13123.54 (15)
O1—Cu1—N1i88.89 (5)C12—C11—C10118.98 (15)
O1i—Cu1—N1i91.11 (5)C12—C11—C13116.96 (14)
N1i—Cu1—N1180.00 (6)N1—C12—C11122.80 (15)
C1—O1—Cu1127.30 (10)N1—C12—H12118.6
Cu1—O4—H4191.8 (19)C11—C12—H12118.6
Cu1—O4—H42114.0 (17)O3—C13—N2122.08 (15)
H41—O4—H42102 (2)O3—C13—C11117.74 (14)
C8—N1—Cu1122.34 (11)N2—C13—C11120.18 (14)
C8—N1—C12118.14 (15)N2—C14—C15113.02 (15)
C12—N1—Cu1119.51 (11)N2—C14—H14A109.0
C13—N2—C14124.35 (14)N2—C14—H14B109.0
C13—N2—C16117.12 (14)C15—C14—H14A109.0
C14—N2—C16118.20 (14)C15—C14—H14B109.0
O1—C1—C2115.78 (14)H14A—C14—H14B107.8
O2—C1—O1126.09 (14)C14—C15—H15A109.5
O2—C1—C2118.12 (14)C14—C15—H15B109.5
C3—C2—C1119.85 (14)C14—C15—H15C109.5
C7—C2—C1120.43 (14)H15A—C15—H15B109.5
C7—C2—C3119.72 (15)H15A—C15—H15C109.5
C2—C3—H3119.8H15B—C15—H15C109.5
C4—C3—C2120.43 (16)N2—C16—C17114.09 (15)
C4—C3—H3119.8N2—C16—H16A108.7
C3—C4—H4121.1N2—C16—H16B108.7
C5—C4—C3117.76 (15)C17—C16—H16A108.7
C5—C4—H4121.1C17—C16—H16B108.7
F1—C5—C4118.30 (15)H16A—C16—H16B107.6
F1—C5—C6117.84 (16)C16—C17—H17A109.5
C6—C5—C4123.86 (15)C16—C17—H17B109.5
C5—C6—C7117.68 (16)C16—C17—H17C109.5
C5—C6—H6121.2H17A—C17—H17B109.5
C7—C6—H6121.2H17A—C17—H17C109.5
C2—C7—H7119.7H17B—C17—H17C109.5
O4i—Cu1—O1—C1−21.24 (14)C14—N2—C16—C17−93.55 (19)
O4—Cu1—O1—C1158.76 (14)O1—C1—C2—C3177.38 (15)
N1i—Cu1—O1—C173.55 (14)O1—C1—C2—C7−1.8 (2)
N1—Cu1—O1—C1−106.45 (14)O2—C1—C2—C3−1.9 (2)
O1—Cu1—N1—C8−35.00 (12)O2—C1—C2—C7178.89 (15)
O1i—Cu1—N1—C8145.00 (12)C1—C2—C3—C4−179.76 (16)
O1—Cu1—N1—C12143.87 (12)C7—C2—C3—C4−0.6 (3)
O1i—Cu1—N1—C12−36.13 (12)C1—C2—C7—C6179.96 (16)
O4i—Cu1—N1—C8−128.95 (12)C3—C2—C7—C60.8 (3)
O4—Cu1—N1—C851.05 (12)C2—C3—C4—C5−0.1 (3)
O4i—Cu1—N1—C1249.92 (12)C3—C4—C5—F1179.97 (16)
O4—Cu1—N1—C12−130.08 (12)C3—C4—C5—C60.7 (3)
Cu1—O1—C1—O230.3 (2)C7—C6—C5—F1−179.76 (16)
Cu1—O1—C1—C2−148.91 (11)C7—C6—C5—C4−0.5 (3)
Cu1—N1—C8—C9179.77 (12)C2—C7—C6—C5−0.3 (3)
C12—N1—C8—C90.9 (2)C10—C9—C8—N10.7 (2)
Cu1—N1—C12—C11178.59 (11)C8—C9—C10—C11−0.7 (2)
C8—N1—C12—C11−2.5 (2)C12—C11—C10—C9−0.8 (2)
C14—N2—C13—O3171.65 (16)C13—C11—C10—C9−172.22 (15)
C14—N2—C13—C11−8.5 (2)C10—C11—C13—O3118.97 (18)
C16—N2—C13—O3−1.6 (2)C10—C11—C13—N2−60.9 (2)
C16—N2—C13—C11178.22 (14)C12—C11—C13—O3−52.6 (2)
C13—N2—C14—C15−89.5 (2)C12—C11—C13—N2127.53 (17)
C16—N2—C14—C1583.7 (2)N1—C12—C11—C102.5 (2)
C13—N2—C16—C1780.1 (2)N1—C12—C11—C13174.46 (14)
D—H···AD—HH···AD···AD—H···A
O4—H41···O2ii0.83 (2)1.90 (2)2.7050 (19)163 (3)
O4—H42···O3iii0.83 (2)2.01 (2)2.834 (2)172 (2)
C6—H6···O2iii0.932.323.211 (2)162
C10—H10···O2iv0.932.483.394 (2)170
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O4—H41⋯O2i0.83 (2)1.90 (2)2.7050 (19)163 (3)
O4—H42⋯O3ii0.83 (2)2.01 (2)2.834 (2)172 (2)
C6—H6⋯O2ii0.932.323.211 (2)162
C10—H10⋯O2iii0.932.483.394 (2)170

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

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Journal:  Am J Clin Nutr       Date:  1974-02       Impact factor: 7.045

3.  Diaqua-bis-(N,N-diethyl-nicotinamide-κN)bis-(4-ethyl-benzoato-κO)cobalt(II).

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Authors:  Tuncer Hökelek; Hakan Dal; Barış Tercan; F Elif Ozbek; Hacali Necefoğlu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-04-30

5.  Diaqua-bis(2-chloro-benzoato-κO)bis-(nicotinamide-κN)nickel(II).

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-03-31

6.  Structure validation in chemical crystallography.

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1.  Aqua-bis-(3-chloro-benzoato-κO)bis-(N,N-di-ethyl-nicotinamide-κN)copper(II).

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