Literature DB >> 22719367

Poly[(μ(2)-benzene-1,3-dicarboxyl-ato-κ(2)O(1):O(3)){μ(2)-1,2-bis-[(1H-imidazol-1-yl)meth-yl]benzene-κ(2)N(3):N(3')}zinc].

Hong Chen, Heng Xu.   

Abstract

In the two-dimensional title coordination polymer, [Zn(C(8)H(4)O(4))(C(14)H(14)N(4))](n), the Zn(II) atom adopts a distorted tetra-hedral geometry, being ligated by two O atoms from two different benzene-1,3-dicarboxyl-ate dianions and two N atoms from two symmetry-related 1,2-bis-(imidazol-1-ylmeth-yl)benzene mol-ecules. The dihedral angles between the imidazole rings and the benzene ring in the neutral ligand are 76.31 (13) and 85.33 (15)°. The Zn(II) atoms are bridged by dicarboxyl-ate ligands, forming chains parallel to the a axis, which are further linked by 1,2-bis-(imidazol-1-ylmeth-yl)benzene mol-ecules, generating a two-dimensional layer structure parallel to the ac plane. The crystal structure is enforced by intra-layer and inter-layer C-H⋯O hydrogen bonds.

Entities:  

Year:  2012        PMID： 22719367      PMCID： PMC3379146          DOI： 10.1107/S1600536812022544

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


Related literature

For background to coordination polymers with bis­(n class="Chemical">imidazole) ligands, see: Qi et al. (2008 ▶); Liu et al. (2009 ▶); Hu et al. (2008 ▶). For related structures, see: Liu et al. (2008 ▶).

Experimental

Crystal data

[Zn(C8H4O4)(C14n class="Species">H14N4)] M = 467.77 Triclinic, a = 10.2028 (14) Å b = 10.2744 (14) Å c = 11.4529 (16) Å α = 75.405 (2)° β = 83.480 (2)° γ = 61.499 (2)° V = 1021.0 (2) Å3 Z = 2 Mo Kα radiation μ = 1.24 mm−1 T = 293 K 0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.739, T max = 0.790 5145 measured reflections 3564 independent reflections 3148 reflections with I > 2σ(I) R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.115 S = 1.02 3564 reflections 280 parameters H-atom parameters constrained Δρmax = 0.59 e Å−3 Δρmin = −0.52 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022544/rz2755sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022544/rz2755Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Zn(C8H4O4)(C14H14N4)]Z = 2
Mr = 467.77F(000) = 480
Triclinic, P1Dx = 1.522 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2028 (14) ÅCell parameters from 2793 reflections
b = 10.2744 (14) Åθ = 2.3–27.9°
c = 11.4529 (16) ŵ = 1.24 mm−1
α = 75.405 (2)°T = 293 K
β = 83.480 (2)°Block, colourless
γ = 61.499 (2)°0.26 × 0.24 × 0.20 mm
V = 1021.0 (2) Å3
Bruker SMART APEX CCD area-detector diffractometer3564 independent reflections
Radiation source: sealed tube3148 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
phi and ω scansθmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −12→12
Tmin = 0.739, Tmax = 0.790k = −12→11
5145 measured reflectionsl = −12→13
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0534P)2 + 0.6759P] where P = (Fo2 + 2Fc2)/3
3564 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.59 e Å−3
0 restraintsΔρmin = −0.52 e Å−3
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.
xyzUiso*/Ueq
Zn1−0.12836 (4)0.60720 (4)1.18865 (3)0.03331 (15)
N1−0.1733 (3)0.7657 (3)1.0358 (2)0.0304 (6)
N2−0.1374 (3)0.8927 (3)0.8612 (2)0.0342 (6)
N3−0.1584 (3)0.7322 (3)0.5120 (3)0.0420 (7)
N4−0.1780 (3)0.6676 (3)0.3492 (3)0.0394 (7)
O10.1045 (3)0.6829 (3)1.1935 (2)0.0464 (6)
O20.0904 (2)0.4788 (3)1.1805 (2)0.0392 (6)
O30.7971 (2)0.4629 (3)1.1786 (2)0.0352 (5)
O40.5906 (3)0.6760 (3)1.1811 (2)0.0400 (6)
C10.1634 (3)0.5512 (4)1.1811 (3)0.0329 (7)
C20.3288 (3)0.4676 (4)1.1651 (3)0.0294 (7)
C30.3983 (4)0.3254 (4)1.1412 (3)0.0366 (8)
H30.34220.27711.13680.044*
C40.5505 (4)0.2531 (4)1.1234 (3)0.0435 (9)
H40.59640.15731.10600.052*
C50.6341 (4)0.3236 (4)1.1315 (3)0.0354 (7)
H50.73650.27521.11940.042*
C60.5668 (3)0.4654 (3)1.1575 (3)0.0273 (6)
C70.4142 (3)0.5373 (4)1.1729 (3)0.0288 (7)
H70.36800.63401.18870.035*
C80.6550 (3)0.5425 (4)1.1731 (3)0.0292 (7)
C9−0.0785 (3)0.7650 (4)0.9477 (3)0.0338 (7)
H90.01740.68580.94580.041*
C10−0.2999 (4)0.9013 (4)1.0029 (3)0.0362 (7)
H10−0.38710.93321.04770.043*
C11−0.2793 (4)0.9816 (4)0.8960 (3)0.0400 (8)
H11−0.34741.07740.85440.048*
C12−0.0539 (4)0.9346 (4)0.7587 (3)0.0403 (8)
H12A0.02890.84270.74120.048*
H12B−0.01290.99310.78090.048*
C13−0.1483 (4)1.0259 (4)0.6473 (3)0.0363 (8)
C14−0.2102 (5)1.1822 (4)0.6227 (4)0.0497 (9)
H14−0.19201.22780.67520.060*
C15−0.2984 (5)1.2723 (5)0.5217 (4)0.0604 (11)
H15−0.33911.37760.50590.072*
C16−0.3248 (5)1.2046 (5)0.4458 (4)0.0608 (11)
H16−0.38531.26430.37810.073*
C17−0.2638 (4)1.0504 (5)0.4677 (3)0.0493 (9)
H17−0.28201.00650.41370.059*
C18−0.1755 (4)0.9577 (4)0.5683 (3)0.0352 (7)
C19−0.1066 (4)0.7864 (4)0.5940 (3)0.0443 (9)
H19A0.00100.74440.58800.053*
H19B−0.12970.74920.67610.053*
C20−0.0952 (4)0.6950 (4)0.4103 (3)0.0402 (8)
H20−0.00310.68880.38460.048*
C21−0.3031 (5)0.6908 (5)0.4175 (4)0.0549 (11)
H21−0.38310.68070.39740.066*
C22−0.2927 (5)0.7305 (5)0.5184 (4)0.0589 (11)
H22−0.36240.75230.57990.071*
U11U22U33U12U13U23
Zn10.0290 (2)0.0372 (2)0.0396 (2)−0.01929 (18)−0.00090 (16)−0.00993 (17)
N10.0260 (13)0.0318 (14)0.0338 (14)−0.0133 (11)−0.0016 (11)−0.0075 (11)
N20.0324 (15)0.0395 (15)0.0329 (15)−0.0183 (12)0.0007 (11)−0.0092 (12)
N30.0473 (18)0.0478 (17)0.0412 (17)−0.0280 (15)0.0012 (14)−0.0152 (14)
N40.0390 (16)0.0522 (18)0.0384 (16)−0.0280 (14)0.0070 (13)−0.0182 (14)
O10.0284 (12)0.0502 (16)0.0675 (17)−0.0200 (12)−0.0001 (12)−0.0209 (13)
O20.0258 (11)0.0460 (14)0.0532 (15)−0.0237 (11)−0.0039 (10)−0.0068 (11)
O30.0211 (11)0.0402 (13)0.0515 (14)−0.0187 (10)0.0002 (10)−0.0128 (11)
O40.0328 (12)0.0372 (14)0.0594 (15)−0.0217 (11)0.0000 (11)−0.0149 (11)
C10.0252 (16)0.044 (2)0.0337 (17)−0.0203 (15)−0.0024 (13)−0.0053 (15)
C20.0244 (15)0.0409 (18)0.0284 (16)−0.0203 (14)−0.0020 (12)−0.0054 (13)
C30.0340 (18)0.048 (2)0.0425 (19)−0.0286 (16)−0.0001 (14)−0.0141 (16)
C40.0371 (19)0.045 (2)0.060 (2)−0.0215 (16)0.0027 (17)−0.0268 (18)
C50.0242 (16)0.0418 (19)0.0441 (19)−0.0166 (15)0.0013 (14)−0.0140 (15)
C60.0223 (15)0.0335 (16)0.0291 (16)−0.0161 (13)−0.0036 (12)−0.0038 (13)
C70.0239 (15)0.0309 (16)0.0347 (17)−0.0151 (13)−0.0014 (13)−0.0067 (13)
C80.0258 (16)0.0408 (19)0.0280 (16)−0.0222 (15)−0.0008 (12)−0.0050 (13)
C90.0266 (16)0.0360 (18)0.0377 (18)−0.0119 (14)−0.0025 (14)−0.0111 (15)
C100.0299 (17)0.0364 (18)0.0429 (19)−0.0150 (15)0.0055 (14)−0.0134 (15)
C110.0320 (18)0.0350 (18)0.047 (2)−0.0111 (15)−0.0015 (15)−0.0086 (15)
C120.0342 (18)0.060 (2)0.0368 (18)−0.0294 (17)0.0026 (14)−0.0127 (16)
C130.0354 (18)0.045 (2)0.0365 (18)−0.0272 (16)0.0069 (14)−0.0084 (15)
C140.057 (2)0.050 (2)0.055 (2)−0.036 (2)0.0094 (19)−0.0143 (19)
C150.065 (3)0.039 (2)0.070 (3)−0.026 (2)0.004 (2)0.002 (2)
C160.062 (3)0.059 (3)0.048 (2)−0.027 (2)−0.010 (2)0.011 (2)
C170.058 (2)0.059 (3)0.0331 (19)−0.030 (2)−0.0040 (17)−0.0056 (17)
C180.0381 (18)0.0412 (19)0.0303 (17)−0.0231 (16)0.0036 (14)−0.0063 (14)
C190.053 (2)0.047 (2)0.0383 (19)−0.0253 (18)−0.0073 (16)−0.0114 (16)
C200.0371 (19)0.048 (2)0.043 (2)−0.0243 (17)0.0016 (16)−0.0150 (17)
C210.054 (2)0.086 (3)0.051 (2)−0.050 (2)0.0143 (19)−0.029 (2)
C220.059 (3)0.090 (3)0.052 (2)−0.050 (3)0.019 (2)−0.030 (2)
Zn1—N11.990 (3)C5—H50.9300
Zn1—O21.984 (2)C6—C71.380 (4)
Zn1—O3i1.993 (2)C6—C81.502 (4)
Zn1—N4ii2.022 (3)C7—H70.9300
N1—C91.315 (4)C9—H90.9300
N1—C101.371 (4)C10—C111.350 (5)
N2—C91.338 (4)C10—H100.9300
N2—C111.370 (4)C11—H110.9300
N2—C121.469 (4)C12—C131.501 (5)
N3—C201.318 (4)C12—H12A0.9700
N3—C221.372 (5)C12—H12B0.9700
N3—C191.459 (4)C13—C141.380 (5)
N4—C201.320 (4)C13—C181.396 (5)
N4—C211.369 (4)C14—C151.380 (6)
N4—Zn1iii2.022 (3)C14—H140.9300
O1—C11.231 (4)C15—C161.360 (6)
O2—C11.281 (4)C15—H150.9300
O3—C81.280 (4)C16—C171.362 (6)
O3—Zn1iv1.993 (2)C16—H160.9300
O4—C81.228 (4)C17—C181.382 (5)
C1—C21.498 (4)C17—H170.9300
C2—C31.372 (5)C18—C191.511 (5)
C2—C71.388 (4)C19—H19A0.9700
C3—C41.382 (5)C19—H19B0.9700
C3—H30.9300C20—H200.9300
C4—C51.380 (5)C21—C221.349 (6)
C4—H40.9300C21—H210.9300
C5—C61.379 (4)C22—H220.9300
N1—Zn1—O2102.90 (10)N2—C9—H9124.3
N1—Zn1—O3i110.16 (10)C11—C10—N1110.0 (3)
O2—Zn1—O3i101.36 (9)C11—C10—H10125.0
N1—Zn1—N4ii120.15 (11)N1—C10—H10125.0
O2—Zn1—N4ii108.84 (11)C10—C11—N2105.8 (3)
O3i—Zn1—N4ii111.41 (10)C10—C11—H11127.1
C9—N1—C10105.4 (3)N2—C11—H11127.1
C9—N1—Zn1125.4 (2)N2—C12—C13112.8 (3)
C10—N1—Zn1129.0 (2)N2—C12—H12A109.0
C9—N2—C11107.3 (3)C13—C12—H12A109.0
C9—N2—C12124.5 (3)N2—C12—H12B109.0
C11—N2—C12127.7 (3)C13—C12—H12B109.0
C20—N3—C22107.2 (3)H12A—C12—H12B107.8
C20—N3—C19126.6 (3)C14—C13—C18119.2 (3)
C22—N3—C19125.7 (3)C14—C13—C12118.6 (3)
C20—N4—C21105.0 (3)C18—C13—C12122.1 (3)
C20—N4—Zn1iii126.6 (2)C13—C14—C15121.3 (4)
C21—N4—Zn1iii128.4 (2)C13—C14—H14119.4
C1—O2—Zn1112.6 (2)C15—C14—H14119.4
C8—O3—Zn1iv104.77 (19)C16—C15—C14118.9 (4)
O1—C1—O2123.4 (3)C16—C15—H15120.5
O1—C1—C2119.9 (3)C14—C15—H15120.5
O2—C1—C2116.6 (3)C15—C16—C17120.8 (4)
C3—C2—C7118.9 (3)C15—C16—H16119.6
C3—C2—C1122.2 (3)C17—C16—H16119.6
C7—C2—C1118.9 (3)C16—C17—C18121.4 (4)
C2—C3—C4120.8 (3)C16—C17—H17119.3
C2—C3—H3119.6C18—C17—H17119.3
C4—C3—H3119.6C17—C18—C13118.3 (3)
C3—C4—C5119.7 (3)C17—C18—C19122.2 (3)
C3—C4—H4120.2C13—C18—C19119.5 (3)
C5—C4—H4120.2N3—C19—C18113.3 (3)
C6—C5—C4120.5 (3)N3—C19—H19A108.9
C6—C5—H5119.8C18—C19—H19A108.9
C4—C5—H5119.8N3—C19—H19B108.9
C5—C6—C7119.1 (3)C18—C19—H19B108.9
C5—C6—C8122.0 (3)H19A—C19—H19B107.7
C7—C6—C8118.9 (3)N3—C20—N4112.2 (3)
C2—C7—C6121.0 (3)N3—C20—H20123.9
C2—C7—H7119.5N4—C20—H20123.9
C6—C7—H7119.5C22—C21—N4109.7 (3)
O4—C8—O3122.7 (3)C22—C21—H21125.2
O4—C8—C6120.2 (3)N4—C21—H21125.2
O3—C8—C6117.1 (3)C21—C22—N3106.0 (3)
N1—C9—N2111.5 (3)C21—C22—H22127.0
N1—C9—H9124.3N3—C22—H22127.0
O2—Zn1—N1—C98.3 (3)C12—N2—C9—N1172.1 (3)
O3i—Zn1—N1—C9−99.1 (3)C9—N1—C10—C11−0.7 (4)
N4ii—Zn1—N1—C9129.4 (2)Zn1—N1—C10—C11174.3 (2)
O2—Zn1—N1—C10−165.8 (3)N1—C10—C11—N20.7 (4)
O3i—Zn1—N1—C1086.8 (3)C9—N2—C11—C10−0.5 (4)
N4ii—Zn1—N1—C10−44.7 (3)C12—N2—C11—C10−172.2 (3)
N1—Zn1—O2—C163.6 (2)C9—N2—C12—C13148.5 (3)
O3i—Zn1—O2—C1177.6 (2)C11—N2—C12—C13−41.2 (5)
N4ii—Zn1—O2—C1−64.9 (2)N2—C12—C13—C1496.4 (4)
Zn1—O2—C1—O14.6 (4)N2—C12—C13—C18−83.5 (4)
Zn1—O2—C1—C2−175.2 (2)C18—C13—C14—C150.1 (5)
O1—C1—C2—C3−174.6 (3)C12—C13—C14—C15−179.8 (3)
O2—C1—C2—C35.2 (5)C13—C14—C15—C160.3 (6)
O1—C1—C2—C74.3 (5)C14—C15—C16—C17−0.9 (7)
O2—C1—C2—C7−175.8 (3)C15—C16—C17—C181.1 (7)
C7—C2—C3—C4−0.9 (5)C16—C17—C18—C13−0.7 (6)
C1—C2—C3—C4178.1 (3)C16—C17—C18—C19−179.9 (4)
C2—C3—C4—C51.0 (6)C14—C13—C18—C170.1 (5)
C3—C4—C5—C60.2 (5)C12—C13—C18—C17−180.0 (3)
C4—C5—C6—C7−1.3 (5)C14—C13—C18—C19179.3 (3)
C4—C5—C6—C8177.0 (3)C12—C13—C18—C19−0.8 (5)
C3—C2—C7—C6−0.3 (5)C20—N3—C19—C1892.4 (4)
C1—C2—C7—C6−179.3 (3)C22—N3—C19—C18−78.1 (5)
C5—C6—C7—C21.4 (5)C17—C18—C19—N3−7.6 (5)
C8—C6—C7—C2−176.9 (3)C13—C18—C19—N3173.3 (3)
Zn1iv—O3—C8—O4−4.1 (4)C22—N3—C20—N4−0.5 (5)
Zn1iv—O3—C8—C6176.6 (2)C19—N3—C20—N4−172.4 (3)
C5—C6—C8—O4170.8 (3)C21—N4—C20—N30.6 (4)
C7—C6—C8—O4−10.8 (5)Zn1iii—N4—C20—N3179.9 (2)
C5—C6—C8—O3−9.9 (5)C20—N4—C21—C22−0.4 (5)
C7—C6—C8—O3168.4 (3)Zn1iii—N4—C21—C22−179.7 (3)
C10—N1—C9—N20.3 (3)N4—C21—C22—N30.2 (5)
Zn1—N1—C9—N2−174.91 (19)C20—N3—C22—C210.2 (5)
C11—N2—C9—N10.1 (4)C19—N3—C22—C21172.2 (4)
D—H···AD—HH···AD···AD—H···A
C9—H9···O3v0.932.383.188 (4)145
C11—H11···O4vi0.932.543.413 (4)157
C14—H14···O1vi0.932.383.306 (7)171
C19—H19B···O2vii0.972.383.200 (4)142
C20—H20···O1iii0.932.343.016 (4)130
C21—H21···O4viii0.932.543.092 (6)119
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C9—H9⋯O3i0.932.383.188 (4)145
C11—H11⋯O4ii0.932.543.413 (4)157
C14—H14⋯O1ii0.932.383.306 (7)171
C19—H19B⋯O2iii0.972.383.200 (4)142
C20—H20⋯O1iv0.932.343.016 (4)130
C21—H21⋯O4v0.932.543.092 (6)119

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

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Authors:  George M Sheldrick
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