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The title compound, [Zn(C12H6O4)(C3H10N2)2]n, has been prepared from zinc(II), naphthalene-2,6-dicarboxylic acid (H2napdc) and 1,3-propyl­enediamine (pren). The Zn atom lies on a crystallographic centre of symmetry and is coordinated by two monodentate naphthalene-2,6-dicarboxyl­ate ligands and two chelating 1,3-propyl­enediamine ligands in a distorted octa­hedral environment. The naphthalene-2,6-dicarboxyl­ate ligands link the Zn atoms, forming a one-dimensional chain structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008117/hg6302sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008117/hg6302Isup2.hkl
Contains datablock I

CCDC reference: 605085

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.041
  • wR factor = 0.105
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

catena-Poly[[bis(1,3-propylenediamine)zinc(II)]-µ-naphthalene-2,6- dicarboxylato-κ2O2:O6] top
Crystal data top
[Zn(C12H6O4)(C3H10N2)2]F(000) = 448
Mr = 427.80Dx = 1.410 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2311 reflections
a = 9.7497 (5) Åθ = 2.1–28.4°
b = 10.1560 (5) ŵ = 1.25 mm1
c = 10.2458 (5) ÅT = 273 K
β = 96.521 (1)°Rod, colorless
V = 1007.95 (9) Å30.32 × 0.25 × 0.12 mm
Z = 2
Data collection top
Bruker AXS area-detector
diffractometer
1771 independent reflections
Radiation source: fine-focus sealed tube1701 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.691, Tmax = 0.865k = 1212
7588 measured reflectionsl = 1212
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0521P)2 + 0.9274P]
where P = (Fo2 + 2Fc2)/3
1771 reflections(Δ/σ)max = 0.001
140 parametersΔρmax = 0.42 e Å3
6 restraintsΔρmin = 0.22 e Å3
Special details top

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*/Ueq
Zn10.50001.00001.00000.02969 (19)
O10.5903 (2)1.1989 (2)1.2690 (2)0.0490 (6)
O20.6741 (2)1.0445 (2)1.1477 (2)0.0413 (5)
N10.5630 (3)0.7977 (2)1.0072 (2)0.0355 (6)
H110.529 (3)0.759 (3)1.0700 (17)0.038 (9)*
H120.525 (3)0.767 (3)0.9343 (14)0.052 (11)*
N20.6322 (3)1.0193 (3)0.8473 (3)0.0390 (6)
H210.589 (3)0.973 (2)0.787 (2)0.048 (11)*
H220.638 (3)1.0986 (13)0.823 (3)0.048 (10)*
C10.7104 (3)0.7689 (3)1.0132 (3)0.0431 (7)
H1A0.72420.67451.02050.052*
H1B0.75820.80951.09110.052*
C20.7716 (4)0.8184 (4)0.8940 (4)0.0533 (9)
H2A0.86610.78720.89860.064*
H2B0.72090.77920.81670.064*
C30.7720 (4)0.9656 (4)0.8757 (4)0.0521 (9)
H3A0.81691.00650.95480.062*
H3B0.82490.98730.80400.062*
C110.6770 (3)1.1137 (3)1.2487 (3)0.0323 (6)
C120.7930 (3)1.0885 (3)1.3560 (3)0.0307 (6)
C130.7969 (3)1.1534 (3)1.4782 (3)0.0366 (7)
H130.73001.21591.49090.044*
C140.8942 (3)0.9998 (3)1.3374 (3)0.0325 (7)
H140.89350.95911.25600.039*
C150.9995 (3)0.9683 (3)1.4382 (3)0.0281 (6)
C161.1031 (3)0.8742 (3)1.4227 (3)0.0347 (7)
H161.10260.83031.34300.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0300 (3)0.0298 (3)0.0285 (3)0.00558 (18)0.00031 (18)0.00105 (18)
O10.0468 (13)0.0515 (13)0.0437 (12)0.0203 (11)0.0166 (10)0.0195 (11)
O20.0372 (12)0.0512 (12)0.0320 (11)0.0131 (10)0.0112 (9)0.0137 (10)
N10.0425 (15)0.0324 (13)0.0306 (13)0.0026 (11)0.0001 (11)0.0018 (11)
N20.0454 (16)0.0357 (15)0.0366 (14)0.0021 (12)0.0072 (12)0.0044 (11)
C10.0468 (18)0.0376 (17)0.0439 (17)0.0160 (14)0.0006 (14)0.0027 (14)
C20.053 (2)0.056 (2)0.053 (2)0.0220 (17)0.0147 (17)0.0001 (17)
C30.043 (2)0.060 (2)0.056 (2)0.0064 (17)0.0175 (17)0.0119 (18)
C110.0320 (15)0.0319 (15)0.0308 (15)0.0016 (12)0.0059 (12)0.0014 (12)
C120.0283 (15)0.0313 (14)0.0311 (14)0.0001 (11)0.0026 (11)0.0011 (11)
C130.0343 (16)0.0397 (16)0.0346 (15)0.0086 (13)0.0017 (12)0.0088 (13)
C140.0333 (16)0.0361 (16)0.0267 (14)0.0027 (12)0.0023 (12)0.0048 (11)
C150.0274 (14)0.0293 (14)0.0268 (14)0.0029 (11)0.0008 (10)0.0012 (11)
C160.0358 (16)0.0400 (16)0.0267 (14)0.0031 (13)0.0030 (12)0.0069 (12)
Geometric parameters (Å, º) top
Zn1—N12.143 (2)C2—C31.507 (5)
Zn1—N1i2.143 (2)C2—H2A0.97
Zn1—N2i2.146 (3)C2—H2B0.97
Zn1—N22.146 (3)C3—H3A0.97
Zn1—O2i2.189 (2)C3—H3B0.97
Zn1—O22.189 (2)C11—C121.507 (4)
O1—C111.243 (4)C12—C141.366 (4)
O2—C111.249 (3)C12—C131.412 (4)
N1—C11.461 (4)C13—C16ii1.354 (4)
N1—H110.85 (1)C13—H130.93
N1—H120.85 (1)C14—C151.408 (4)
N2—C31.466 (5)C14—H140.93
N2—H210.85 (1)C15—C161.412 (4)
N2—H220.85 (1)C15—C15ii1.419 (6)
C1—C21.505 (5)C16—C13ii1.354 (4)
C1—H1A0.97C16—H160.93
C1—H1B0.97
N1—Zn1—N1i180.0 (1)C2—C1—H1B109.2
N1—Zn1—N2i94.7 (1)H1A—C1—H1B107.9
N1i—Zn1—N2i85.3 (1)C3—C2—C1116.0 (3)
N1—Zn1—N285.3 (1)C3—C2—H2A108.3
N1i—Zn1—N294.7 (1)C1—C2—H2A108.3
N2i—Zn1—N2180.0 (1)C3—C2—H2B108.3
N1—Zn1—O2i91.3 (1)C1—C2—H2B108.3
N1i—Zn1—O2i88.7 (1)H2A—C2—H2B107.4
N2i—Zn1—O2i90.1 (1)N2—C3—C2112.2 (3)
N2—Zn1—O2i89.9 (1)N2—C3—H3A109.2
N1—Zn1—O288.7 (1)C2—C3—H3A109.2
N1i—Zn1—O291.3 (1)N2—C3—H3B109.2
N2i—Zn1—O289.9 (1)C2—C3—H3B109.2
N2—Zn1—O290.1 (1)H3A—C3—H3B107.9
O2i—Zn1—O2180.0 (1)O1—C11—O2125.4 (3)
C11—O2—Zn1129.2 (2)O1—C11—C12117.6 (2)
C1—N1—Zn1118.05 (19)O2—C11—C12117.0 (2)
C1—N1—H11110 (2)C14—C12—C13119.0 (3)
Zn1—N1—H11109 (2)C14—C12—C11120.3 (3)
C1—N1—H12107 (2)C13—C12—C11120.7 (2)
Zn1—N1—H12103 (2)C16ii—C13—C12120.9 (3)
H11—N1—H12109.4 (16)C16ii—C13—H13119.6
C3—N2—Zn1116.3 (2)C12—C13—H13119.6
C3—N2—H21108 (3)C12—C14—C15121.7 (3)
Zn1—N2—H21101 (2)C12—C14—H14119.2
C3—N2—H22109 (2)C15—C14—H14119.2
Zn1—N2—H22111 (2)C14—C15—C16122.8 (3)
H21—N2—H22110.6 (17)C14—C15—C15ii118.8 (3)
N1—C1—C2112.2 (3)C16—C15—C15ii118.4 (3)
N1—C1—H1A109.2C13ii—C16—C15121.2 (3)
C2—C1—H1A109.2C13ii—C16—H16119.4
N1—C1—H1B109.2C15—C16—H16119.4
N1—Zn1—O2—C11134.8 (3)C1—C2—C3—N266.9 (4)
N1i—Zn1—O2—C1145.2 (3)Zn1—O2—C11—O119.8 (5)
N2i—Zn1—O2—C1140.2 (3)Zn1—O2—C11—C12158.2 (2)
N2—Zn1—O2—C11139.8 (3)O1—C11—C12—C14177.5 (3)
N2i—Zn1—N1—C1131.4 (2)O2—C11—C12—C144.3 (4)
N2—Zn1—N1—C148.6 (2)O1—C11—C12—C134.2 (4)
O2i—Zn1—N1—C1138.3 (2)O2—C11—C12—C13174.0 (3)
O2—Zn1—N1—C141.7 (2)C14—C12—C13—C16ii1.9 (5)
N1—Zn1—N2—C349.2 (3)C11—C12—C13—C16ii176.4 (3)
N1i—Zn1—N2—C3130.8 (3)C13—C12—C14—C152.1 (4)
O2i—Zn1—N2—C3140.5 (3)C11—C12—C14—C15176.2 (3)
O2—Zn1—N2—C339.5 (3)C12—C14—C15—C16178.2 (3)
Zn1—N1—C1—C261.8 (3)C12—C14—C15—C15ii0.5 (5)
N1—C1—C2—C364.9 (4)C14—C15—C16—C13ii179.8 (3)
Zn1—N2—C3—C264.4 (4)C15ii—C15—C16—C13ii1.5 (5)
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+2, y+2, z+3.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H12···O1i0.85 (1)2.28 (2)3.047 (3)150 (3)
N1—H11···O1iii0.85 (1)2.21 (2)3.046 (3)167 (3)
N2—H21···O1i0.85 (1)2.49 (2)3.232 (4)146 (3)
N2—H22···O1iv0.85 (1)2.17 (2)2.988 (3)164 (3)
Symmetry codes: (i) x+1, y+2, z+2; (iii) x+1, y1/2, z+5/2; (iv) x, y+5/2, z1/2.
 

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