Literature DB >> 21579040

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

Hacali Necefoğlu, Efdal Cimen, Barış Tercan, Emel Ermiş, Tuncer Hökelek.   

Abstract

In the centrosymmetric mononuclear title complex, [Co(C(8)H(7)O(2))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], the Co(II) ion is located on an inversion center. The asymmetric unit contains one 4-methyl-benzoate (PMB) anion, one N,N-diethyl-nicotinamide (DENA) ligand and one coordinated water mol-ecule. The four O atoms in the equatorial plane around the Co(II) ion form a slightly distorted square-planar arrangement, while the slightly distorted octa-hedral coordination is completed by the two pyridine N atoms of the DENA ligands in the axial positions. The dihedral angle between the carboxyl-ate group and the attached benzene ring is 3.73 (14)°, while the pyridine and benzene rings are oriented at a dihedral angle of 77.28 (6)°. In the crystal structure, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network parallel to (001). The structure is further stabilized by π-π contacts between the pyridine rings [centroid-centroid distance = 3.544 (1) Å] and weak C-H⋯π inter-actions involving the benzene ring.

Entities:  

Year:  2010        PMID： 21579040      PMCID： PMC2979235          DOI： 10.1107/S1600536810013954

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


Related literature

For niacin, see: Krishnamachari (1974 ▶), and for the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek et al. (1996 ▶, 2009a ▶,b ▶,c ▶); Hökelek & Necefoğlu (1998 ▶); Necefoğlu et al. (2010 ▶).

Experimental

Crystal data

[Co(C8H7O2)2(C10H14N2O)2(H2O)2] M = 721.70 Triclinic, a = 7.2791 (2) Å b = 8.5453 (2) Å c = 16.0438 (4) Å α = 84.090 (3)° β = 77.583 (3)° γ = 67.271 (2)° V = 898.71 (4) Å3 Z = 1 Mo Kα radiation μ = 0.53 mm−1 T = 100 K 0.35 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.852, T max = 0.922 15243 measured reflections 4484 independent reflections 3821 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.090 S = 1.04 4484 reflections 234 parameters 3 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.86 e Å−3 Δρmin = −0.55 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: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013954/ci5076sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013954/ci5076Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Co(C8H7O2)2(C10H14N2O)2(H2O)2]Z = 1
Mr = 721.70F(000) = 381
Triclinic, P1Dx = 1.334 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2791 (2) ÅCell parameters from 7347 reflections
b = 8.5453 (2) Åθ = 2.6–28.3°
c = 16.0438 (4) ŵ = 0.53 mm−1
α = 84.090 (3)°T = 100 K
β = 77.583 (3)°Block, pink
γ = 67.271 (2)°0.35 × 0.25 × 0.15 mm
V = 898.71 (4) Å3
Bruker Kappa APEXII CCD area-detector diffractometer4484 independent reflections
Radiation source: fine-focus sealed tube3821 reflections with I > 2σ(I)
graphiteRint = 0.025
φ and ω scansθmax = 28.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −9→9
Tmin = 0.852, Tmax = 0.922k = −11→11
15243 measured reflectionsl = −21→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0314P)2 + 0.8168P] where P = (Fo2 + 2Fc2)/3
4484 reflections(Δ/σ)max = 0.001
234 parametersΔρmax = 0.86 e Å−3
3 restraintsΔρmin = −0.55 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 > 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.
xyzUiso*/Ueq
Co10.00000.00000.00000.01216 (9)
O1−0.07573 (18)0.12790 (16)−0.20025 (8)0.0182 (3)
O20.11412 (18)0.12158 (15)−0.10611 (7)0.0152 (2)
O30.84302 (19)−0.32653 (16)−0.12244 (8)0.0190 (3)
O40.22201 (18)0.01547 (16)0.06192 (8)0.0164 (3)
H410.191 (4)−0.036 (3)0.1190 (12)0.058 (9)*
H420.211 (4)0.117 (2)0.0762 (16)0.046 (8)*
N10.2241 (2)−0.23699 (18)−0.04865 (9)0.0138 (3)
N20.8480 (2)−0.42543 (18)−0.24793 (9)0.0170 (3)
C10.0833 (3)0.1274 (2)−0.18126 (11)0.0142 (3)
C20.2508 (3)0.1341 (2)−0.25355 (11)0.0148 (3)
C30.2310 (3)0.1313 (2)−0.33787 (11)0.0168 (3)
H30.11610.1212−0.34920.020*
C40.3813 (3)0.1434 (2)−0.40496 (11)0.0189 (4)
H40.36550.1425−0.46090.023*
C50.5557 (3)0.1569 (2)−0.38953 (11)0.0191 (4)
C60.5781 (3)0.1543 (2)−0.30536 (12)0.0192 (4)
H60.69520.1603−0.29400.023*
C70.4276 (3)0.1429 (2)−0.23807 (11)0.0165 (3)
H70.44500.1411−0.18220.020*
C80.7177 (3)0.1732 (3)−0.46257 (13)0.0298 (5)
H8A0.72310.1117−0.51040.045*
H8B0.84680.1275−0.44510.045*
H8C0.68610.2907−0.47860.045*
C90.1932 (3)−0.3834 (2)−0.03785 (11)0.0146 (3)
H90.0700−0.3831−0.00630.018*
C100.3371 (3)−0.5349 (2)−0.07173 (11)0.0162 (3)
H100.3102−0.6339−0.06310.019*
C110.5216 (3)−0.5369 (2)−0.11857 (11)0.0157 (3)
H110.6200−0.6366−0.14260.019*
C120.5562 (3)−0.3860 (2)−0.12890 (10)0.0138 (3)
C130.4048 (3)−0.2405 (2)−0.09221 (11)0.0146 (3)
H130.4297−0.1407−0.09810.018*
C140.7599 (3)−0.3773 (2)−0.16750 (11)0.0147 (3)
C150.7528 (3)−0.4745 (2)−0.30709 (11)0.0203 (4)
H15A0.6229−0.4762−0.27690.024*
H15B0.8377−0.5886−0.32610.024*
C160.7198 (4)−0.3567 (3)−0.38450 (15)0.0397 (6)
H16A0.6555−0.3943−0.42030.060*
H16B0.8482−0.3575−0.41600.060*
H16C0.6348−0.2435−0.36630.060*
C171.0549 (3)−0.4277 (2)−0.27880 (12)0.0211 (4)
H17A1.1183−0.5004−0.32780.025*
H17B1.1337−0.4769−0.23440.025*
C181.0623 (3)−0.2529 (3)−0.30397 (14)0.0289 (5)
H18A1.2009−0.2634−0.32260.043*
H18B1.0014−0.1803−0.25560.043*
H18C0.9891−0.2050−0.34950.043*
U11U22U33U12U13U23
Co10.01068 (16)0.01085 (16)0.01383 (17)−0.00297 (12)−0.00131 (12)−0.00186 (12)
O10.0155 (6)0.0201 (6)0.0191 (6)−0.0067 (5)−0.0040 (5)0.0007 (5)
O20.0162 (6)0.0136 (6)0.0154 (6)−0.0054 (5)−0.0021 (5)−0.0013 (4)
O30.0168 (6)0.0199 (6)0.0224 (7)−0.0086 (5)−0.0028 (5)−0.0044 (5)
O40.0148 (6)0.0155 (6)0.0200 (6)−0.0065 (5)−0.0032 (5)−0.0023 (5)
N10.0125 (7)0.0129 (7)0.0156 (7)−0.0041 (6)−0.0029 (5)−0.0011 (5)
N20.0163 (7)0.0158 (7)0.0183 (7)−0.0067 (6)0.0004 (6)−0.0028 (6)
C10.0150 (8)0.0073 (7)0.0173 (8)−0.0013 (6)−0.0024 (7)−0.0008 (6)
C20.0158 (8)0.0100 (8)0.0166 (8)−0.0030 (6)−0.0023 (7)−0.0013 (6)
C30.0160 (8)0.0154 (8)0.0181 (8)−0.0046 (7)−0.0036 (7)−0.0013 (6)
C40.0208 (9)0.0194 (9)0.0149 (8)−0.0056 (7)−0.0030 (7)−0.0016 (7)
C50.0181 (9)0.0192 (9)0.0182 (9)−0.0071 (7)0.0008 (7)−0.0014 (7)
C60.0170 (8)0.0195 (9)0.0219 (9)−0.0076 (7)−0.0029 (7)−0.0023 (7)
C70.0171 (8)0.0150 (8)0.0164 (8)−0.0045 (7)−0.0041 (7)−0.0013 (6)
C80.0252 (10)0.0423 (13)0.0219 (10)−0.0159 (10)0.0025 (8)−0.0027 (9)
C90.0125 (8)0.0154 (8)0.0161 (8)−0.0056 (7)−0.0025 (6)−0.0001 (6)
C100.0172 (8)0.0125 (8)0.0203 (9)−0.0065 (7)−0.0041 (7)−0.0010 (6)
C110.0153 (8)0.0125 (8)0.0172 (8)−0.0028 (7)−0.0025 (7)−0.0024 (6)
C120.0134 (8)0.0145 (8)0.0137 (8)−0.0054 (7)−0.0028 (6)−0.0001 (6)
C130.0147 (8)0.0128 (8)0.0171 (8)−0.0058 (7)−0.0032 (7)−0.0002 (6)
C140.0139 (8)0.0095 (7)0.0194 (8)−0.0031 (6)−0.0027 (7)−0.0001 (6)
C150.0228 (9)0.0198 (9)0.0177 (9)−0.0075 (8)−0.0019 (7)−0.0034 (7)
C160.0536 (15)0.0448 (14)0.0296 (12)−0.0251 (12)−0.0195 (11)0.0120 (10)
C170.0173 (9)0.0182 (9)0.0242 (9)−0.0063 (7)0.0048 (7)−0.0047 (7)
C180.0288 (11)0.0219 (10)0.0342 (11)−0.0136 (9)0.0065 (9)−0.0028 (8)
Co1—O22.0885 (12)C7—C61.388 (2)
Co1—O2i2.0885 (12)C7—H70.93
Co1—O42.1209 (12)C8—H8A0.96
Co1—O4i2.1209 (12)C8—H8B0.96
Co1—N12.1439 (14)C8—H8C0.96
Co1—N1i2.1439 (14)C9—C101.386 (2)
O1—C11.257 (2)C9—H90.93
O2—C11.266 (2)C10—H100.93
O3—C141.238 (2)C11—C101.385 (2)
O4—H410.996 (15)C11—H110.93
O4—H420.889 (16)C12—C111.394 (2)
N1—C91.342 (2)C12—C131.385 (2)
N1—C131.341 (2)C12—C141.506 (2)
N2—C141.340 (2)C13—H130.93
N2—C151.465 (2)C15—C161.516 (3)
N2—C171.474 (2)C15—H15A0.97
C1—C21.505 (2)C15—H15B0.97
C2—C31.394 (2)C16—H16A0.96
C3—H30.93C16—H16B0.96
C4—C31.387 (2)C16—H16C0.96
C4—C51.393 (3)C17—C181.525 (3)
C4—H40.93C17—H17A0.97
C5—C81.511 (3)C17—H17B0.97
C6—C51.392 (3)C18—H18A0.96
C6—H60.93C18—H18B0.96
C7—C21.393 (2)C18—H18C0.96
O2i—Co1—O2180.00 (5)C5—C8—H8B109.5
O2—Co1—O488.07 (5)C5—C8—H8C109.5
O2i—Co1—O491.93 (5)H8A—C8—H8B109.5
O2—Co1—O4i91.93 (5)H8A—C8—H8C109.5
O2i—Co1—O4i88.07 (5)H8B—C8—H8C109.5
O2—Co1—N188.47 (5)N1—C9—C10122.83 (15)
O2i—Co1—N191.53 (5)N1—C9—H9118.6
O2—Co1—N1i91.53 (5)C10—C9—H9118.6
O2i—Co1—N1i88.47 (5)C9—C10—H10120.5
O4—Co1—O4i180.00 (8)C11—C10—C9119.08 (16)
O4—Co1—N186.58 (5)C11—C10—H10120.5
O4i—Co1—N193.42 (5)C10—C11—C12118.47 (15)
O4—Co1—N1i93.42 (5)C10—C11—H11120.8
O4i—Co1—N1i86.58 (5)C12—C11—H11120.8
N1i—Co1—N1180.00 (8)C11—C12—C14123.16 (15)
C1—O2—Co1126.53 (11)C13—C12—C11118.72 (15)
Co1—O4—H41101.8 (17)C13—C12—C14117.57 (15)
Co1—O4—H42118.7 (18)N1—C13—C12123.04 (16)
H41—O4—H42101 (2)N1—C13—H13118.5
C9—N1—Co1123.36 (11)C12—C13—H13118.5
C13—N1—Co1118.83 (11)O3—C14—N2121.55 (16)
C13—N1—C9117.81 (14)O3—C14—C12118.01 (15)
C14—N2—C15124.66 (15)N2—C14—C12120.44 (15)
C14—N2—C17117.31 (15)N2—C15—C16113.39 (16)
C15—N2—C17118.03 (14)N2—C15—H15A108.9
O1—C1—O2125.19 (16)N2—C15—H15B108.9
O1—C1—C2117.52 (15)C16—C15—H15A108.9
O2—C1—C2117.30 (15)C16—C15—H15B108.9
C3—C2—C1120.15 (16)H15A—C15—H15B107.7
C7—C2—C1121.17 (15)C15—C16—H16A109.5
C7—C2—C3118.67 (16)C15—C16—H16B109.5
C2—C3—H3119.7C15—C16—H16C109.5
C4—C3—C2120.57 (17)H16A—C16—H16B109.5
C4—C3—H3119.7H16A—C16—H16C109.5
C3—C4—C5120.76 (17)H16B—C16—H16C109.5
C3—C4—H4119.6N2—C17—C18113.83 (15)
C5—C4—H4119.6N2—C17—H17A108.8
C4—C5—C8120.76 (17)N2—C17—H17B108.8
C6—C5—C4118.59 (16)C18—C17—H17A108.8
C6—C5—C8120.65 (17)C18—C17—H17B108.8
C5—C6—H6119.6H17A—C17—H17B107.7
C7—C6—C5120.79 (17)C17—C18—H18A109.5
C7—C6—H6119.6C17—C18—H18B109.5
C2—C7—H7119.7C17—C18—H18C109.5
C6—C7—C2120.57 (16)H18A—C18—H18B109.5
C6—C7—H7119.7H18A—C18—H18C109.5
C5—C8—H8A109.5H18B—C18—H18C109.5
O4—Co1—O2—C1163.36 (13)C15—N2—C17—C18100.98 (19)
O4i—Co1—O2—C1−16.64 (13)O1—C1—C2—C7176.64 (15)
N1—Co1—O2—C176.73 (13)O2—C1—C2—C7−3.4 (2)
N1i—Co1—O2—C1−103.27 (13)O1—C1—C2—C3−3.4 (2)
O2—Co1—N1—C9−147.01 (13)O2—C1—C2—C3176.48 (15)
O2i—Co1—N1—C932.99 (13)C1—C2—C3—C4177.72 (15)
O4—Co1—N1—C9124.83 (13)C7—C2—C3—C4−2.4 (3)
O4i—Co1—N1—C9−55.17 (13)C5—C4—C3—C20.6 (3)
O2—Co1—N1—C1332.98 (13)C3—C4—C5—C61.3 (3)
O2i—Co1—N1—C13−147.02 (13)C3—C4—C5—C8−178.90 (18)
O4—Co1—N1—C13−55.18 (13)C7—C6—C5—C4−1.6 (3)
O4i—Co1—N1—C13124.82 (13)C7—C6—C5—C8178.64 (18)
Co1—O2—C1—O131.7 (2)C6—C7—C2—C1−177.98 (16)
Co1—O2—C1—C2−148.20 (11)C6—C7—C2—C32.1 (2)
Co1—N1—C9—C10178.06 (12)C2—C7—C6—C5−0.1 (3)
C13—N1—C9—C10−1.9 (2)N1—C9—C10—C110.3 (3)
Co1—N1—C13—C12−177.42 (13)C12—C11—C10—C90.8 (3)
C9—N1—C13—C122.6 (2)C13—C12—C11—C10−0.2 (2)
C15—N2—C14—O3−175.13 (16)C14—C12—C11—C10171.09 (16)
C15—N2—C14—C125.7 (2)C11—C12—C13—N1−1.5 (3)
C17—N2—C14—O34.4 (2)C14—C12—C13—N1−173.31 (15)
C17—N2—C14—C12−174.73 (15)C11—C12—C14—O3−118.02 (19)
C14—N2—C15—C16116.2 (2)C11—C12—C14—N261.2 (2)
C17—N2—C15—C16−63.3 (2)C13—C12—C14—O353.4 (2)
C14—N2—C17—C18−78.6 (2)C13—C12—C14—N2−127.43 (17)
Cg1 is the centroid of the C2–C7 ring.
D—H···AD—HH···AD···AD—H···A
O4—H41···O1ii1.00 (2)1.69 (2)2.6443 (18)160 (3)
O4—H42···O3iii0.89 (2)1.88 (2)2.7557 (18)170 (2)
C6—H6···O1iv0.932.403.249 (3)152
C11—H11···O1v0.932.423.339 (2)168
C17—H17A···Cg1vi0.972.953.594 (2)125
Table 1

Selected bond lengths (Å)

Co1—O22.0885 (12)
Co1—O42.1209 (12)
Co1—N12.1439 (14)
Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O4—H41⋯O1i1.00 (2)1.69 (2)2.6443 (18)160 (3)
O4—H42⋯O3ii0.89 (2)1.88 (2)2.7557 (18)170 (2)
C6—H6⋯O10.932.403.249 (3)152
C11—H11⋯O10.932.423.339 (2)168
C17—H17A⋯Cg1iii0.972.953.594 (2)125

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

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3.  Diaqua-bis(2-chloro-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)manganese(II).

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4.  Diaqua-bis(2-bromo-benzoato-κO)bis-(nicotinamide-κN)zinc(II).

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

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6.  Diaqua-bis(4-methyl-benzoato-κO)bis-(nicotinamide-κN)nickel(II).

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7.  Structure validation in chemical crystallography.

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  7 in total
  1 in total

1.  Diaqua-bis-(2-bromo-benzoato-κO)bis-(N,N-diethyl-nicotinamide-κN)cobalt(II).

Authors:  Tuncer Hökelek; Güner Saka; Barış Tercan; Füreya Elif Oztürkkan; Hacali Necefoğlu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-08-18
  1 in total

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