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The title bis-nicotinate zinc chloride, [Zn(C6H4NO2)Cl(C6H5NO2)]n, has an infinite head-to-tail one-dimensional chain structure. The compound was synthesized under mild hydro­thermal conditions. The ZnII atom exhibits a distorted tetra­hedral coordination geometry. The structure is statistically disordered, with 0.5 site occupancy for the Zn atom and the H atom located on the pyridine N atom. As a result, Zn positions in the crystal structure alternate between two sites related by a crystallographic twofold axis and rows of mol­ecules are formed, supported by strong N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051282/om2066sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051282/om2066Isup2.hkl
Contains datablock I

CCDC reference: 633977

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.050
  • wR factor = 0.134
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Zn1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.29 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT and SADABS (Sheldrick, 2003); program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL.

catena-Poly[[chloro(pyridinium-3-carboxylato-κO)zinc(II)]- µ-nicotinato-κ2O:N] top
Crystal data top
[Zn(C6H4NO2)Cl(C6H5NO2)]F(000) = 696
Mr = 346.03Dx = 1.782 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4195 reflections
a = 13.0493 (2) Åθ = 3.1–26.5°
b = 7.7050 (1) ŵ = 2.12 mm1
c = 12.9115 (1) ÅT = 173 K
β = 96.439 (1)°Plate, colourless
V = 1290.00 (3) Å30.20 × 0.08 × 0.04 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
1341 independent reflections
Radiation source: fine-focus sealed tube1104 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
ω scansθmax = 26.5°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1616
Tmin = 0.676, Tmax = 0.920k = 99
6430 measured reflectionsl = 1616
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0709P)2 + 5.3068P]
where P = (Fo2 + 2Fc2)/3
1341 reflections(Δ/σ)max < 0.001
96 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.56 e Å3
Special details top

Experimental. Spectroscopic analysis: IR (KBr pellet, ν, cm-1): 3020 (CC, s), 1742 (CO, s), 1534 (CC, m), 1395 (C—H, s), 1243 (C—N, s), 1062 (C—O, m), 764 (C—H, m).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.45298 (6)0.06492 (10)0.18285 (5)0.0256 (3)0.50
Cl10.50000.19001 (19)0.25000.0526 (5)
O10.6264 (2)0.2194 (4)0.22467 (18)0.0430 (7)
O20.5120 (2)0.2083 (4)0.08291 (19)0.0392 (6)
N10.8221 (2)0.5186 (4)0.0759 (3)0.0400 (8)
H10.88170.55000.10930.048*0.50
C20.7570 (3)0.4240 (5)0.1242 (3)0.0344 (8)
H20.77620.39000.19440.041*
C30.6626 (3)0.3740 (4)0.0757 (2)0.0266 (7)
C40.6349 (3)0.4246 (4)0.0274 (2)0.0262 (7)
H40.56990.39210.06280.031*
C50.7034 (3)0.5228 (4)0.0775 (3)0.0300 (8)
H50.68580.55910.14750.036*
C60.7971 (3)0.5672 (5)0.0248 (3)0.0377 (9)
H60.84490.63260.05920.045*
C70.5942 (3)0.2583 (5)0.1318 (3)0.0352 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0275 (4)0.0358 (5)0.0142 (4)0.0035 (3)0.0056 (3)0.0011 (3)
Cl10.0706 (10)0.0382 (8)0.0415 (8)0.0000.0259 (7)0.000
O10.0637 (19)0.0511 (17)0.0156 (12)0.0106 (14)0.0105 (12)0.0068 (11)
O20.0452 (16)0.0482 (16)0.0262 (13)0.0042 (13)0.0133 (12)0.0055 (11)
N10.0276 (16)0.0468 (19)0.0444 (19)0.0026 (14)0.0010 (14)0.0211 (16)
C20.0339 (19)0.049 (2)0.0203 (16)0.0111 (17)0.0001 (14)0.0083 (15)
C30.0346 (18)0.0304 (17)0.0157 (14)0.0078 (14)0.0073 (13)0.0017 (12)
C40.0302 (17)0.0298 (17)0.0185 (15)0.0026 (14)0.0023 (13)0.0006 (13)
C50.0353 (18)0.0306 (18)0.0253 (17)0.0015 (15)0.0086 (14)0.0004 (14)
C60.0338 (19)0.0302 (19)0.051 (2)0.0039 (15)0.0157 (17)0.0117 (17)
C70.055 (2)0.0323 (19)0.0219 (17)0.0135 (17)0.0202 (17)0.0022 (14)
Geometric parameters (Å, º) top
Zn1—O21.924 (3)N1—Zn1iii2.104 (3)
Zn1—Zn1i2.0088 (14)N1—H10.8800
Zn1—O1i2.048 (3)C2—C31.372 (5)
Zn1—N1ii2.104 (3)C2—H20.9500
Zn1—Cl12.2061 (15)C3—C41.395 (4)
Zn1—C72.514 (4)C3—C71.505 (5)
Cl1—Zn1i2.2061 (15)C4—C51.386 (5)
O1—C71.261 (4)C4—H40.9500
O1—Zn1i2.048 (3)C5—C61.374 (5)
O2—C71.243 (5)C5—H50.9500
N1—C21.327 (5)C6—H60.9500
N1—C61.357 (5)
O2—Zn1—Zn1i109.10 (10)C6—N1—H1119.8
O2—Zn1—O1i108.91 (12)N1—C2—C3121.9 (3)
Zn1i—Zn1—O1i78.26 (9)N1—C2—H2119.1
O2—Zn1—N1ii90.79 (14)C3—C2—H2119.1
Zn1i—Zn1—N1ii159.94 (12)C2—C3—C4118.7 (3)
O1i—Zn1—N1ii93.14 (12)C2—C3—C7119.8 (3)
O2—Zn1—Cl1131.31 (9)C4—C3—C7121.4 (3)
Zn1i—Zn1—Cl162.92 (3)C5—C4—C3119.0 (3)
O1i—Zn1—Cl1115.15 (8)C5—C4—H4120.5
N1ii—Zn1—Cl1106.06 (1)C3—C4—H4120.5
O2—Zn1—C728.80 (11)C4—C5—C6119.4 (3)
Zn1i—Zn1—C780.30 (9)C4—C5—H5120.3
O1i—Zn1—C7103.99 (11)C6—C5—H5120.3
N1ii—Zn1—C7119.58 (14)N1—C6—C5120.7 (4)
Cl1—Zn1—C7116.80 (9)N1—C6—H6119.7
Zn1i—Cl1—Zn154.16 (5)C5—C6—H6119.7
C7—O1—Zn1i123.8 (3)O2—C7—O1125.9 (4)
C7—O2—Zn1103.0 (2)O2—C7—C3117.6 (3)
C2—N1—C6120.3 (3)O1—C7—C3116.5 (4)
C2—N1—Zn1iii107.4 (3)O2—C7—Zn148.22 (18)
C6—N1—Zn1iii132.2 (3)O1—C7—Zn177.7 (2)
C2—N1—H1119.8C3—C7—Zn1165.8 (3)
O2—Zn1—Cl1—Zn1i92.29 (13)Zn1i—O1—C7—Zn11.0 (2)
O1i—Zn1—Cl1—Zn1i60.50 (9)C2—C3—C7—O2176.1 (3)
N1ii—Zn1—Cl1—Zn1i161.93 (11)C4—C3—C7—O20.4 (5)
C7—Zn1—Cl1—Zn1i61.95 (10)C2—C3—C7—O13.3 (5)
Zn1i—Zn1—O2—C70.9 (2)C4—C3—C7—O1179.7 (3)
O1i—Zn1—O2—C784.7 (2)C2—C3—C7—Zn1173.7 (8)
N1ii—Zn1—O2—C7178.3 (2)C4—C3—C7—Zn12.7 (12)
Cl1—Zn1—O2—C769.4 (3)Zn1i—Zn1—C7—O2179.1 (2)
C6—N1—C2—C30.8 (5)O1i—Zn1—C7—O2103.9 (2)
Zn1iii—N1—C2—C3178.9 (3)N1ii—Zn1—C7—O22.0 (3)
N1—C2—C3—C40.0 (5)Cl1—Zn1—C7—O2128.0 (2)
N1—C2—C3—C7176.5 (3)O2—Zn1—C7—O1180.0 (4)
C2—C3—C4—C50.3 (5)Zn1i—Zn1—C7—O10.86 (18)
C7—C3—C4—C5176.2 (3)O1i—Zn1—C7—O176.1 (2)
C3—C4—C5—C60.3 (5)N1ii—Zn1—C7—O1177.98 (19)
C2—N1—C6—C51.5 (5)Cl1—Zn1—C7—O152.0 (2)
Zn1iii—N1—C6—C5178.2 (3)O2—Zn1—C7—C32.8 (9)
C4—C5—C6—N11.2 (5)Zn1i—Zn1—C7—C3178.1 (10)
Zn1—O2—C7—O10.1 (4)O1i—Zn1—C7—C3106.7 (10)
Zn1—O2—C7—C3179.2 (2)N1ii—Zn1—C7—C34.8 (10)
Zn1i—O1—C7—O21.0 (5)Cl1—Zn1—C7—C3125.2 (10)
Zn1i—O1—C7—C3179.8 (2)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x1/2, y1/2, z; (iii) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2iii0.882.152.870 (4)139
C5—H5···O1iv0.952.443.302 (4)151
Symmetry codes: (iii) x+1/2, y+1/2, z; (iv) x, y+1, z1/2.
 

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