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The title compound, [Zn(C7H4NO4)2(C10H14N2O)2(H2O)2], crystallizes as centrosymmetric mononuclear mol­ecules with octahedrally coordinated zinc, all pairs of equivalent ligands being mutually trans. Intramolecular hydrogen bonding links each aqua ligand with an uncoordinated carboxyl­ate O atom, and intermolecular hydrogen bonding between aqua ligands and the carbonyl O atoms of N,N-diethyl­nicotin­amide ligands link the mol­ecules together into chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015033/na6092sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015033/na6092Isup2.hkl
Contains datablock I

CCDC reference: 175337

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.026
  • wR factor = 0.068
  • Data-to-parameter ratio = 12.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.905 Tmax scaled 0.868 Tmin scaled 0.743

Comment top

The title compound, (I), was prepared as part of a series of studies of the coordination chemistry of the ligand N,N-diethylnicotinamide (DENA). It has a molecular structure (Fig. 1) very similar to that of the corresponding complex in which 2-hydroxybenzoate (salicylate) replaces 4-nitrobenzoate, reported in a parallel publication (Necefoglu et al., 2001). Coordination of zinc is close to regular octahedral, with all pairs of equivalent ligands mutually trans across a crystallographic inversion centre.

Each aqua ligand is involved as donor in two hydrogen bonds. One of these is intramolecular, to an uncoordinated carboxylate oxygen atom, lengthening the CO nominal double bond to almost the same as C—O for the coordinated O atom. The other is intermolecular, linking the molecules together in chains along the a axis.

Experimental top

The title compound was prepared by the reaction of 4.34 g (0.01 mol) of [Zn(OH2)2(4-O2NC6H4COO)2] and 2.56 g (0.02 mol) of diethylnicotinamide in 100 ml water. The solution was filtered and set aside for crystallization at ambient temperature for a few days. Suitable colourless crystals were obtained.

Refinement top

H atoms were placed geometrically and refined with a riding model (including free rotation about C—C bonds), and with Uiso constrained to be 1.2 (1.5 for methyl groups) times Ueq of the carrier atom, except for aqua ligand H atoms, which were refined freely with individual Uiso.

Computing details top

Data collection: DIF4 (Stoe & Cie, 1988); cell refinement: DIF4; data reduction: local programs; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with atom labels and 50% probability ellipsoids for non-H atoms.
[Figure 2] Fig. 2. View of two molecules and the unit-cell outline, showing intramolecular and intermolecular hydrogen bonding as dashed lines.
Diaquabis(N,N-diethylnicotinamide)bis(4-nitrobenzoato)zinc(II) top
Crystal data top
[Zn(C7H4NO4)2(C10H14N2O)2(H2O)2]Z = 1
Mr = 790.09F(000) = 412
Triclinic, P1Dx = 1.436 Mg m3
a = 7.211 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.588 (4) ÅCell parameters from 36 reflections
c = 16.515 (7) Åθ = 10.7–12.5°
α = 96.00 (2)°µ = 0.74 mm1
β = 100.79 (2)°T = 160 K
γ = 112.09 (3)°Block, colourless
V = 913.6 (7) Å30.42 × 0.27 × 0.19 mm
Data collection top
Stoe-Siemens four-circle
diffractometer
2889 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω/θ scans with on–line profile fitting (Clegg, 1981)h = 88
Absorption correction: ψ scan
(XPREP; Sheldrick, 1997)
k = 1010
Tmin = 0.821, Tmax = 0.959l = 1919
6298 measured reflections5 standard reflections every 60 min
3214 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0275P)2 + 0.4095P]
where P = (Fo2 + 2Fc2)/3
3214 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
[Zn(C7H4NO4)2(C10H14N2O)2(H2O)2]γ = 112.09 (3)°
Mr = 790.09V = 913.6 (7) Å3
Triclinic, P1Z = 1
a = 7.211 (3) ÅMo Kα radiation
b = 8.588 (4) ŵ = 0.74 mm1
c = 16.515 (7) ÅT = 160 K
α = 96.00 (2)°0.42 × 0.27 × 0.19 mm
β = 100.79 (2)°
Data collection top
Stoe-Siemens four-circle
diffractometer
2889 reflections with I > 2σ(I)
Absorption correction: ψ scan
(XPREP; Sheldrick, 1997)
Rint = 0.020
Tmin = 0.821, Tmax = 0.9595 standard reflections every 60 min
6298 measured reflections intensity decay: 1%
3214 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.068H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.33 e Å3
3214 reflectionsΔρmin = 0.26 e Å3
251 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn0.50000.50000.50000.01697 (9)
O10.79004 (19)0.50312 (18)0.56174 (8)0.0227 (3)
H1A0.813 (4)0.570 (3)0.6084 (17)0.049 (7)*
H1B0.787 (4)0.414 (3)0.5760 (14)0.039 (7)*
N10.6747 (2)0.71783 (17)0.45183 (8)0.0183 (3)
C10.6537 (3)0.8666 (2)0.46307 (10)0.0201 (3)
H10.56230.87790.49560.024*
C20.7599 (3)1.0046 (2)0.42920 (11)0.0220 (4)
H20.74131.10830.43850.026*
C30.8932 (3)0.9895 (2)0.38164 (11)0.0218 (4)
H30.96591.08170.35700.026*
C40.9188 (2)0.8365 (2)0.37061 (10)0.0182 (3)
C50.8087 (2)0.7051 (2)0.40749 (10)0.0186 (3)
H50.82880.60180.40120.022*
C61.0807 (3)0.8142 (2)0.33073 (10)0.0199 (4)
O21.21846 (19)0.78446 (16)0.37503 (8)0.0270 (3)
N21.0770 (2)0.82976 (18)0.25073 (9)0.0229 (3)
C70.9084 (3)0.8481 (2)0.19266 (11)0.0297 (4)
H7A0.96750.94760.16610.036*
H7B0.81630.87170.22500.036*
C80.7817 (4)0.6905 (3)0.12447 (15)0.0529 (6)
H8A0.66440.70590.09110.079*
H8B0.73060.58990.15030.079*
H8C0.86810.67410.08800.079*
C91.2497 (3)0.8191 (2)0.21772 (12)0.0294 (4)
H9A1.38080.88740.26030.035*
H9B1.25490.87120.16700.035*
C101.2343 (4)0.6371 (3)0.19520 (15)0.0405 (5)
H10A1.35500.64020.17510.061*
H10B1.10840.56980.15100.061*
H10C1.22950.58440.24500.061*
O30.50606 (18)0.33955 (14)0.39517 (7)0.0205 (3)
C110.3897 (3)0.3038 (2)0.32227 (10)0.0184 (3)
O40.20852 (18)0.29485 (15)0.30447 (7)0.0240 (3)
C120.4800 (3)0.2719 (2)0.24946 (10)0.0191 (3)
C130.6763 (3)0.2716 (2)0.26350 (11)0.0207 (4)
H130.75490.29130.31940.025*
C140.7586 (3)0.2426 (2)0.19654 (11)0.0230 (4)
H140.89220.24170.20570.028*
C150.6390 (3)0.2151 (2)0.11612 (11)0.0232 (4)
C160.4439 (3)0.2160 (2)0.09983 (11)0.0244 (4)
H160.36640.19740.04380.029*
C170.3649 (3)0.2446 (2)0.16737 (11)0.0223 (4)
H170.23140.24570.15780.027*
N30.7240 (2)0.1864 (2)0.04415 (9)0.0288 (4)
O50.8860 (2)0.1667 (2)0.05764 (9)0.0508 (4)
O60.6269 (2)0.1804 (2)0.02622 (8)0.0408 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.01512 (15)0.01988 (15)0.01763 (15)0.00705 (11)0.00675 (10)0.00605 (10)
O10.0206 (7)0.0264 (7)0.0252 (7)0.0128 (5)0.0069 (5)0.0072 (6)
N10.0146 (7)0.0212 (7)0.0200 (7)0.0070 (6)0.0058 (6)0.0062 (5)
C10.0177 (8)0.0247 (8)0.0211 (8)0.0106 (7)0.0075 (7)0.0049 (7)
C20.0221 (9)0.0217 (8)0.0266 (9)0.0122 (7)0.0080 (7)0.0062 (7)
C30.0200 (9)0.0220 (8)0.0246 (9)0.0074 (7)0.0079 (7)0.0096 (7)
C40.0149 (8)0.0216 (8)0.0180 (8)0.0071 (7)0.0040 (6)0.0051 (6)
C50.0173 (8)0.0199 (8)0.0202 (8)0.0085 (7)0.0056 (7)0.0046 (6)
C60.0175 (8)0.0176 (8)0.0258 (9)0.0064 (7)0.0080 (7)0.0064 (7)
O20.0214 (6)0.0356 (7)0.0317 (7)0.0163 (6)0.0106 (5)0.0132 (6)
N20.0256 (8)0.0261 (8)0.0258 (8)0.0148 (6)0.0144 (6)0.0108 (6)
C70.0378 (11)0.0367 (10)0.0255 (9)0.0227 (9)0.0121 (8)0.0146 (8)
C80.0507 (15)0.0595 (15)0.0454 (13)0.0287 (13)0.0042 (11)0.0016 (11)
C90.0346 (11)0.0293 (10)0.0364 (10)0.0162 (8)0.0253 (9)0.0144 (8)
C100.0518 (14)0.0359 (11)0.0529 (13)0.0267 (10)0.0336 (11)0.0163 (10)
O30.0213 (6)0.0238 (6)0.0182 (6)0.0099 (5)0.0072 (5)0.0044 (5)
C110.0203 (9)0.0140 (7)0.0209 (8)0.0050 (6)0.0081 (7)0.0059 (6)
O40.0171 (6)0.0303 (7)0.0246 (6)0.0087 (5)0.0073 (5)0.0042 (5)
C120.0198 (8)0.0157 (8)0.0214 (8)0.0052 (7)0.0078 (7)0.0044 (6)
C130.0199 (9)0.0221 (8)0.0199 (8)0.0087 (7)0.0041 (7)0.0040 (7)
C140.0188 (9)0.0258 (9)0.0255 (9)0.0102 (7)0.0063 (7)0.0037 (7)
C150.0255 (9)0.0249 (9)0.0214 (9)0.0107 (7)0.0102 (7)0.0035 (7)
C160.0236 (9)0.0302 (9)0.0191 (8)0.0118 (8)0.0034 (7)0.0033 (7)
C170.0178 (8)0.0256 (9)0.0235 (9)0.0091 (7)0.0045 (7)0.0045 (7)
N30.0275 (9)0.0370 (9)0.0237 (8)0.0137 (7)0.0104 (7)0.0032 (7)
O50.0353 (9)0.0909 (13)0.0347 (8)0.0367 (9)0.0119 (7)0.0008 (8)
O60.0475 (9)0.0642 (10)0.0221 (7)0.0314 (8)0.0146 (6)0.0116 (7)
Geometric parameters (Å, º) top
Zn—O1i2.1373 (15)C8—H8A0.980
Zn—O12.1373 (15)C8—H8B0.980
Zn—O3i2.1149 (14)C8—H8C0.980
Zn—O32.1149 (14)C9—C101.525 (3)
Zn—N12.1527 (16)C9—H9A0.990
Zn—N1i2.1527 (16)C9—H9B0.990
O1—H1A0.86 (3)C10—H10A0.980
O1—H1B0.81 (3)C10—H10B0.980
N1—C11.340 (2)C10—H10C0.980
N1—C51.345 (2)C11—O31.264 (2)
C1—C21.386 (2)C11—O41.255 (2)
C1—H10.950C11—C121.518 (2)
C2—C31.383 (2)C12—C131.392 (3)
C2—H20.950C12—C171.395 (2)
C3—C41.392 (2)C13—C141.392 (2)
C3—H30.950C13—H130.950
C4—C51.387 (2)C14—C151.384 (3)
C4—C61.504 (2)C14—H140.950
C5—H50.950C15—C161.385 (3)
C6—O21.243 (2)C15—N31.474 (2)
C6—N21.338 (2)C16—C171.384 (2)
N2—C71.470 (2)C16—H160.950
N2—C91.479 (2)C17—H170.950
C7—C81.517 (3)N3—O61.225 (2)
C7—H7A0.990N3—O51.225 (2)
C7—H7B0.990
O3i—Zn—O3180.0C8—C7—H7B108.9
O3i—Zn—O1i87.54 (6)H7A—C7—H7B107.8
O3—Zn—O1i92.46 (6)C7—C8—H8A109.5
O3i—Zn—O192.46 (6)C7—C8—H8B109.5
O3—Zn—O187.54 (6)H8A—C8—H8B109.5
O1i—Zn—O1180.0C7—C8—H8C109.5
O3i—Zn—N191.46 (6)H8A—C8—H8C109.5
O3—Zn—N188.54 (6)H8B—C8—H8C109.5
O1i—Zn—N193.29 (6)N2—C9—C10114.03 (16)
O1—Zn—N186.71 (6)N2—C9—H9A108.7
O3i—Zn—N1i88.54 (6)C10—C9—H9A108.7
O3—Zn—N1i91.46 (6)N2—C9—H9B108.7
O1i—Zn—N1i86.71 (6)C10—C9—H9B108.7
O1—Zn—N1i93.29 (6)H9A—C9—H9B107.6
N1—Zn—N1i180.0C9—C10—H10A109.5
Zn—O1—H1A99.5 (17)C9—C10—H10B109.5
Zn—O1—H1B116.0 (17)H10A—C10—H10B109.5
H1A—O1—H1B103 (2)C9—C10—H10C109.5
C1—N1—C5118.01 (14)H10A—C10—H10C109.5
C1—N1—Zn122.64 (11)H10B—C10—H10C109.5
C5—N1—Zn119.34 (11)C11—O3—Zn125.41 (11)
N1—C1—C2122.72 (16)O4—C11—O3126.30 (15)
N1—C1—H1118.6O4—C11—C12117.12 (15)
C2—C1—H1118.6O3—C11—C12116.58 (15)
C3—C2—C1119.11 (16)C13—C12—C17119.74 (16)
C3—C2—H2120.4C13—C12—C11120.96 (15)
C1—C2—H2120.4C17—C12—C11119.29 (16)
C2—C3—C4118.71 (15)C14—C13—C12120.75 (16)
C2—C3—H3120.6C14—C13—H13119.6
C4—C3—H3120.6C12—C13—H13119.6
C5—C4—C3118.59 (16)C15—C14—C13117.69 (17)
C5—C4—C6117.71 (15)C15—C14—H14121.2
C3—C4—C6123.16 (15)C13—C14—H14121.2
N1—C5—C4122.82 (15)C14—C15—C16123.11 (16)
N1—C5—H5118.6C14—C15—N3118.69 (16)
C4—C5—H5118.6C16—C15—N3118.18 (16)
O2—C6—N2121.81 (16)C17—C16—C15118.22 (16)
O2—C6—C4117.72 (15)C17—C16—H16120.9
N2—C6—C4120.45 (15)C15—C16—H16120.9
C6—N2—C7124.48 (15)C16—C17—C12120.48 (17)
C6—N2—C9117.40 (15)C16—C17—H17119.8
C7—N2—C9118.04 (15)C12—C17—H17119.8
N2—C7—C8113.16 (17)O6—N3—O5123.39 (16)
N2—C7—H7A108.9O6—N3—C15118.20 (16)
C8—C7—H7A108.9O5—N3—C15118.39 (15)
N2—C7—H7B108.9
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O4i0.86 (3)1.82 (3)2.659 (2)164 (3)
O1—H1B···O2ii0.81 (3)1.95 (3)2.765 (2)173 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Zn(C7H4NO4)2(C10H14N2O)2(H2O)2]
Mr790.09
Crystal system, space groupTriclinic, P1
Temperature (K)160
a, b, c (Å)7.211 (3), 8.588 (4), 16.515 (7)
α, β, γ (°)96.00 (2), 100.79 (2), 112.09 (3)
V3)913.6 (7)
Z1
Radiation typeMo Kα
µ (mm1)0.74
Crystal size (mm)0.42 × 0.27 × 0.19
Data collection
DiffractometerStoe-Siemens four-circle
diffractometer
Absorption correctionψ scan
(XPREP; Sheldrick, 1997)
Tmin, Tmax0.821, 0.959
No. of measured, independent and
observed [I > 2σ(I)] reflections
6298, 3214, 2889
Rint0.020
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.068, 1.10
No. of reflections3214
No. of parameters251
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.26

Computer programs: DIF4 (Stoe & Cie, 1988), DIF4, SHELXTL (Sheldrick, 1997), SHELXTL and local programs.

Selected geometric parameters (Å, º) top
Zn—O12.1373 (15)C11—O31.264 (2)
Zn—O32.1149 (14)C11—O41.255 (2)
Zn—N12.1527 (16)
O3—Zn—O187.54 (6)O1—Zn—N186.71 (6)
O3—Zn—N188.54 (6)C11—O3—Zn125.41 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O4i0.86 (3)1.82 (3)2.659 (2)164 (3)
O1—H1B···O2ii0.81 (3)1.95 (3)2.765 (2)173 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1.
 

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