Aminobenzoic acid derivatives are widely used in the preparation of new coordination polymers since they contain O-atom donors, as well as N-atom donors, and have a rich variety of coordination modes which can lead to polymers with intriguing structures and interesting properties. Two new coordination polymers incorporating 1-aminobenzene-3,4,5-tricarboxylic acid (H3abtc), namely, poly[(μ3-1-amino-5-carboxybenzene-3,4-dicarboxylato)diaquacadmium(II)], [Cd(C9H5NO6)(H2O)2]n, (I), and poly[[bis(μ5-1-aminobenzene-3,4,5-tricarboxylato)triaquatrizinc(II)] dihydrate], {[Zn3(C9H4NO6)2(H2O)3]·2H2O}n, (II), have been prepared and structurally characterized by single-crystal X-ray diffraction. In polymer (I), each tridentate 1-amino-5-carboxybenzene-3,4-dicarboxylate (Habtc2−) ligand coordinates to three CdII ions to form a two-dimensional network structure, in which all of the CdII ions and Habtc2− ligands are equivalent, respectively. Polymer (II) also exhibits a two-dimensional network structure, in which three crystallographically independent ZnII ions are bridged by two crystallographically independent pentadentate 1-aminobenzene-3,4,5-tricarboxylate (abtc3−) ligands. This indicates that changing the metal ion can influence the coordination mode of the H3abtc-derived ligand and further influence the detailed architecture of the polymer. Moreover, the IR spectra, thermogravimetric analyses and fluorescence properties were investigated.
Supporting information
CCDC references: 1936986; 1936985
For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).
Poly[(µ
3-1-amino-5-carboxybenzene-3,4-dicarboxylato)diaquacadmium(II)] (I)
top
Crystal data top
[Cd(C9H5NO6)(H2O)2] | F(000) = 728 |
Mr = 371.57 | Dx = 2.373 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0872 (7) Å | Cell parameters from 9796 reflections |
b = 8.4024 (9) Å | θ = 2.7–27.6° |
c = 17.4973 (17) Å | µ = 2.14 mm−1 |
β = 93.608 (3)° | T = 293 K |
V = 1039.89 (18) Å3 | Block, colorless |
Z = 4 | 0.12 × 0.11 × 0.11 mm |
Data collection top
Bruker D8 VENTURE PHOTON diffractometer | 2274 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
φ and ω scans | θmax = 27.6°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −9→9 |
| k = −10→10 |
44567 measured reflections | l = −22→22 |
2408 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.017 | Hydrogen site location: mixed |
wR(F2) = 0.047 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0259P)2 + 1.2021P] where P = (Fo2 + 2Fc2)/3 |
2408 reflections | (Δ/σ)max = 0.001 |
172 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −0.68 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cd1 | 0.53243 (2) | 0.03978 (2) | 0.30278 (2) | 0.01334 (6) | |
O1 | 0.0986 (2) | 0.59398 (18) | 0.69228 (8) | 0.0211 (3) | |
O2 | 0.0667 (2) | 0.33526 (17) | 0.67775 (8) | 0.0190 (3) | |
O3 | 0.40891 (18) | 0.17638 (16) | 0.62236 (7) | 0.0147 (3) | |
O4 | 0.14838 (19) | 0.08829 (16) | 0.55573 (8) | 0.0167 (3) | |
O5 | 0.4505 (2) | 0.12327 (17) | 0.44511 (8) | 0.0233 (3) | |
H5 | 0.487487 | 0.140032 | 0.489727 | 0.035* | |
O6 | 0.3975 (2) | 0.26649 (18) | 0.34159 (8) | 0.0242 (3) | |
O7 | 0.2199 (2) | −0.05433 (19) | 0.28082 (9) | 0.0235 (3) | |
H7A | 0.196320 | −0.115065 | 0.242545 | 0.035* | |
H7B | 0.127630 | 0.010385 | 0.279785 | 0.035* | |
O8 | 0.8638 (2) | 0.08840 (18) | 0.31563 (9) | 0.0224 (3) | |
H8A | 0.908445 | 0.052979 | 0.358542 | 0.034* | |
H8B | 0.883435 | 0.188109 | 0.318042 | 0.034* | |
N1 | 0.2275 (2) | 0.81742 (18) | 0.43778 (9) | 0.0133 (3) | |
H1A | 0.114644 | 0.857017 | 0.448851 | 0.016* | |
H1B | 0.234974 | 0.816377 | 0.386591 | 0.016* | |
C1 | 0.2378 (2) | 0.6560 (2) | 0.46868 (10) | 0.0105 (3) | |
C2 | 0.1783 (2) | 0.6330 (2) | 0.54118 (10) | 0.0118 (3) | |
H2 | 0.132091 | 0.718635 | 0.568021 | 0.014* | |
C3 | 0.1866 (3) | 0.4828 (2) | 0.57476 (10) | 0.0108 (3) | |
C4 | 0.2562 (2) | 0.3535 (2) | 0.53438 (10) | 0.0095 (3) | |
C5 | 0.3117 (2) | 0.3786 (2) | 0.45945 (10) | 0.0100 (3) | |
C6 | 0.3032 (3) | 0.5305 (2) | 0.42715 (10) | 0.0114 (3) | |
H6 | 0.341570 | 0.546872 | 0.377895 | 0.014* | |
C7 | 0.1135 (3) | 0.4673 (2) | 0.65348 (10) | 0.0125 (3) | |
C8 | 0.2718 (3) | 0.1911 (2) | 0.57353 (10) | 0.0120 (3) | |
C9 | 0.3905 (2) | 0.2459 (2) | 0.41315 (10) | 0.0124 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.01794 (8) | 0.01286 (8) | 0.00962 (8) | 0.00230 (5) | 0.00405 (5) | −0.00012 (5) |
O1 | 0.0387 (8) | 0.0137 (7) | 0.0121 (6) | −0.0006 (6) | 0.0103 (6) | −0.0013 (5) |
O2 | 0.0288 (7) | 0.0147 (7) | 0.0143 (6) | −0.0026 (6) | 0.0082 (6) | 0.0022 (5) |
O3 | 0.0152 (6) | 0.0148 (6) | 0.0141 (6) | 0.0024 (5) | 0.0001 (5) | 0.0041 (5) |
O4 | 0.0180 (6) | 0.0121 (6) | 0.0200 (7) | −0.0017 (5) | 0.0009 (5) | 0.0010 (5) |
O5 | 0.0374 (8) | 0.0146 (7) | 0.0182 (7) | 0.0096 (6) | 0.0036 (6) | 0.0001 (6) |
O6 | 0.0415 (9) | 0.0206 (7) | 0.0112 (6) | 0.0129 (7) | 0.0066 (6) | −0.0012 (6) |
O7 | 0.0213 (7) | 0.0292 (8) | 0.0200 (7) | −0.0027 (6) | 0.0005 (6) | −0.0075 (6) |
O8 | 0.0282 (8) | 0.0162 (7) | 0.0230 (7) | −0.0027 (6) | 0.0023 (6) | 0.0024 (6) |
N1 | 0.0166 (7) | 0.0101 (7) | 0.0137 (7) | 0.0025 (6) | 0.0048 (6) | 0.0038 (6) |
C1 | 0.0111 (8) | 0.0083 (8) | 0.0121 (8) | 0.0004 (6) | 0.0005 (6) | 0.0021 (6) |
C2 | 0.0137 (8) | 0.0107 (8) | 0.0112 (8) | 0.0013 (6) | 0.0025 (6) | −0.0013 (6) |
C3 | 0.0119 (8) | 0.0121 (8) | 0.0084 (8) | −0.0007 (6) | 0.0016 (6) | 0.0000 (6) |
C4 | 0.0095 (7) | 0.0095 (8) | 0.0095 (8) | 0.0000 (6) | 0.0001 (6) | 0.0010 (6) |
C5 | 0.0102 (7) | 0.0100 (8) | 0.0098 (8) | 0.0012 (6) | 0.0009 (6) | −0.0012 (6) |
C6 | 0.0123 (8) | 0.0135 (9) | 0.0085 (8) | 0.0007 (6) | 0.0025 (6) | 0.0011 (6) |
C7 | 0.0126 (8) | 0.0161 (9) | 0.0089 (8) | 0.0014 (7) | 0.0022 (6) | 0.0012 (7) |
C8 | 0.0142 (8) | 0.0109 (8) | 0.0114 (8) | 0.0019 (6) | 0.0059 (6) | 0.0009 (7) |
C9 | 0.0128 (8) | 0.0121 (8) | 0.0125 (8) | 0.0005 (7) | 0.0028 (6) | −0.0022 (7) |
Geometric parameters (Å, º) top
Cd1—O6 | 2.2553 (14) | O8—H8A | 0.8501 |
Cd1—O3i | 2.2625 (13) | O8—H8B | 0.8499 |
Cd1—O1ii | 2.3098 (14) | N1—C1 | 1.460 (2) |
Cd1—O7 | 2.3603 (16) | N1—H1A | 0.8989 |
Cd1—O8 | 2.3801 (15) | N1—H1B | 0.9006 |
Cd1—O2ii | 2.4524 (14) | C1—C2 | 1.375 (2) |
Cd1—C7ii | 2.7105 (18) | C1—C6 | 1.378 (2) |
O1—C7 | 1.271 (2) | C2—C3 | 1.392 (3) |
O2—C7 | 1.241 (2) | C2—H2 | 0.9300 |
O3—C8 | 1.259 (2) | C3—C4 | 1.403 (2) |
O4—C8 | 1.255 (2) | C3—C7 | 1.507 (2) |
O5—C9 | 1.235 (2) | C4—C5 | 1.408 (2) |
O5—H5 | 0.8200 | C4—C8 | 1.527 (2) |
O6—C9 | 1.268 (2) | C5—C6 | 1.396 (2) |
O7—H7A | 0.8501 | C5—C9 | 1.506 (2) |
O7—H7B | 0.8499 | C6—H6 | 0.9300 |
| | | |
O6—Cd1—O3i | 124.73 (5) | C1—N1—H1B | 110.8 |
O6—Cd1—O1ii | 140.83 (5) | H1A—N1—H1B | 109.1 |
O3i—Cd1—O1ii | 93.12 (5) | C2—C1—C6 | 120.79 (16) |
O6—Cd1—O7 | 85.45 (6) | C2—C1—N1 | 117.45 (16) |
O3i—Cd1—O7 | 87.80 (5) | C6—C1—N1 | 121.76 (16) |
O1ii—Cd1—O7 | 86.48 (5) | C1—C2—C3 | 120.63 (16) |
O6—Cd1—O8 | 105.13 (6) | C1—C2—H2 | 119.7 |
O3i—Cd1—O8 | 86.49 (5) | C3—C2—H2 | 119.7 |
O1ii—Cd1—O8 | 84.92 (5) | C2—C3—C4 | 119.79 (16) |
O7—Cd1—O8 | 169.41 (5) | C2—C3—C7 | 117.16 (16) |
O6—Cd1—O2ii | 88.54 (5) | C4—C3—C7 | 123.03 (16) |
O3i—Cd1—O2ii | 146.65 (5) | C3—C4—C5 | 118.72 (16) |
O1ii—Cd1—O2ii | 54.90 (5) | C3—C4—C8 | 118.95 (15) |
O7—Cd1—O2ii | 98.20 (5) | C5—C4—C8 | 122.33 (15) |
O8—Cd1—O2ii | 81.86 (5) | C6—C5—C4 | 120.44 (16) |
O6—Cd1—C7ii | 115.36 (5) | C6—C5—C9 | 117.83 (15) |
O3i—Cd1—C7ii | 119.87 (5) | C4—C5—C9 | 121.66 (16) |
O1ii—Cd1—C7ii | 27.88 (5) | C1—C6—C5 | 119.59 (16) |
O7—Cd1—C7ii | 95.13 (5) | C1—C6—H6 | 120.2 |
O8—Cd1—C7ii | 80.04 (5) | C5—C6—H6 | 120.2 |
O2ii—Cd1—C7ii | 27.22 (5) | O2—C7—O1 | 122.23 (17) |
C7—O1—Cd1iii | 93.88 (11) | O2—C7—C3 | 120.32 (16) |
C7—O2—Cd1iii | 88.06 (11) | O1—C7—C3 | 117.42 (16) |
C8—O3—Cd1i | 125.28 (12) | O2—C7—Cd1iii | 64.72 (10) |
C9—O5—H5 | 111.6 | O1—C7—Cd1iii | 58.24 (10) |
C9—O6—Cd1 | 103.05 (12) | C3—C7—Cd1iii | 171.27 (13) |
Cd1—O7—H7A | 117.7 | O4—C8—O3 | 126.66 (17) |
Cd1—O7—H7B | 120.1 | O4—C8—C4 | 118.29 (16) |
H7A—O7—H7B | 104.7 | O3—C8—C4 | 115.03 (16) |
Cd1—O8—H8A | 109.5 | O5—C9—O6 | 121.81 (17) |
Cd1—O8—H8B | 109.4 | O5—C9—C5 | 120.17 (16) |
H8A—O8—H8B | 104.5 | O6—C9—C5 | 117.99 (16) |
C1—N1—H1A | 106.7 | | |
| | | |
C6—C1—C2—C3 | 1.3 (3) | Cd1iii—O1—C7—O2 | 10.3 (2) |
N1—C1—C2—C3 | −179.04 (16) | Cd1iii—O1—C7—C3 | −171.28 (14) |
C1—C2—C3—C4 | 0.0 (3) | C2—C3—C7—O2 | 159.58 (18) |
C1—C2—C3—C7 | −178.34 (16) | C4—C3—C7—O2 | −18.7 (3) |
C2—C3—C4—C5 | −1.6 (3) | C2—C3—C7—O1 | −18.9 (3) |
C7—C3—C4—C5 | 176.58 (16) | C4—C3—C7—O1 | 162.83 (18) |
C2—C3—C4—C8 | 177.48 (16) | Cd1i—O3—C8—O4 | −2.7 (3) |
C7—C3—C4—C8 | −4.3 (3) | Cd1i—O3—C8—C4 | 175.88 (10) |
C3—C4—C5—C6 | 2.1 (3) | C3—C4—C8—O4 | 102.6 (2) |
C8—C4—C5—C6 | −177.02 (16) | C5—C4—C8—O4 | −78.4 (2) |
C3—C4—C5—C9 | 179.02 (16) | C3—C4—C8—O3 | −76.2 (2) |
C8—C4—C5—C9 | −0.1 (3) | C5—C4—C8—O3 | 102.9 (2) |
C2—C1—C6—C5 | −0.9 (3) | Cd1—O6—C9—O5 | 0.1 (2) |
N1—C1—C6—C5 | 179.49 (16) | Cd1—O6—C9—C5 | 178.32 (13) |
C4—C5—C6—C1 | −0.8 (3) | C6—C5—C9—O5 | 159.62 (18) |
C9—C5—C6—C1 | −177.90 (16) | C4—C5—C9—O5 | −17.4 (3) |
Cd1iii—O2—C7—O1 | −9.63 (19) | C6—C5—C9—O6 | −18.6 (3) |
Cd1iii—O2—C7—C3 | 171.95 (16) | C4—C5—C9—O6 | 164.38 (17) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1/2, −y+1/2, z−1/2; (iii) x−1/2, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O3 | 0.82 | 2.44 | 3.165 (2) | 148 |
O7—H7A···O6iv | 0.85 | 1.86 | 2.706 (2) | 170 |
O7—H7B···O8v | 0.85 | 2.11 | 2.894 (2) | 152 |
O8—H8A···O4i | 0.85 | 1.97 | 2.702 (2) | 143 |
O8—H8B···O1vi | 0.85 | 1.85 | 2.687 (2) | 170 |
N1—H1A···O4vii | 0.90 | 1.92 | 2.789 (2) | 163 |
N1—H1B···O7viii | 0.90 | 2.14 | 2.948 (2) | 148 |
Symmetry codes: (i) −x+1, −y, −z+1; (iv) −x+1/2, y−1/2, −z+1/2; (v) x−1, y, z; (vi) −x+1, −y+1, −z+1; (vii) −x, −y+1, −z+1; (viii) x, y+1, z. |
Poly[[bis(µ
5-1-aminobenzene-3,4,5-tricarboxylato)triaquatrizinc(II)]
dihydrate] (II)
top
Crystal data top
[Zn3(C9H4NO6)2(H2O)3]·2H2O | Z = 2 |
Mr = 730.45 | F(000) = 732 |
Triclinic, P1 | Dx = 2.188 Mg m−3 |
a = 7.2480 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3135 (3) Å | Cell parameters from 9818 reflections |
c = 17.2244 (6) Å | θ = 2.3–27.6° |
α = 102.620 (1)° | µ = 3.32 mm−1 |
β = 95.860 (1)° | T = 293 K |
γ = 99.150 (1)° | Block, colorless |
V = 1108.83 (7) Å3 | 0.12 × 0.12 × 0.11 mm |
Data collection top
Bruker D8 VENTURE PHOTON diffractometer | 4499 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
φ and ω scans | θmax = 27.6°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −9→9 |
| k = −12→12 |
37612 measured reflections | l = −22→22 |
5127 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: mixed |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.036P)2 + 1.9472P] where P = (Fo2 + 2Fc2)/3 |
5127 reflections | (Δ/σ)max = 0.001 |
361 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.94 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.87219 (5) | 0.69503 (3) | 0.11907 (2) | 0.02115 (8) | |
Zn2 | 0.60872 (4) | 0.43581 (3) | 0.75121 (2) | 0.02023 (8) | |
Zn3 | 0.64942 (5) | 0.35556 (3) | 0.39787 (2) | 0.02101 (8) | |
O1 | 0.8732 (5) | 0.1089 (3) | −0.10728 (15) | 0.0583 (8) | |
O2 | 0.9912 (4) | 0.3163 (3) | −0.02030 (18) | 0.0526 (7) | |
O3 | 0.6403 (3) | 0.4457 (2) | 0.04913 (11) | 0.0239 (4) | |
O4 | 0.8967 (3) | 0.49141 (19) | 0.13778 (11) | 0.0214 (4) | |
O5 | 0.5195 (3) | 0.3817 (2) | 0.20643 (12) | 0.0294 (4) | |
O6 | 0.6518 (3) | 0.2572 (2) | 0.28748 (11) | 0.0312 (5) | |
O7 | 0.3606 (3) | 0.0614 (2) | 0.37549 (12) | 0.0342 (5) | |
O8 | 0.4556 (3) | 0.2868 (2) | 0.45816 (12) | 0.0303 (5) | |
O9 | 0.2285 (3) | 0.42890 (19) | 0.57425 (12) | 0.0253 (4) | |
O10 | 0.5100 (3) | 0.4258 (2) | 0.63313 (11) | 0.0268 (4) | |
O11 | 0.0737 (3) | 0.1913 (2) | 0.76341 (11) | 0.0236 (4) | |
O12 | 0.3554 (3) | 0.3168 (2) | 0.76381 (12) | 0.0278 (4) | |
O13 | 0.6814 (3) | 0.4505 (2) | 0.87674 (12) | 0.0310 (5) | |
H13A | 0.788445 | 0.490823 | 0.904287 | 0.046* | |
H13B | 0.615725 | 0.502643 | 0.905397 | 0.046* | |
O14 | 0.8587 (3) | 0.5704 (2) | 0.74974 (13) | 0.0310 (5) | |
H14A | 0.956955 | 0.567734 | 0.780509 | 0.046* | |
H14B | 0.863525 | 0.663484 | 0.753459 | 0.046* | |
O15 | 0.7138 (3) | 0.2368 (3) | 0.72031 (15) | 0.0449 (6) | |
H15A | 0.658116 | 0.152598 | 0.690542 | 0.067* | |
H15B | 0.820396 | 0.211448 | 0.728392 | 0.067* | |
O16 | 0.8303 (4) | 0.8547 (3) | 0.75834 (16) | 0.0506 (7) | |
H16A | 0.755036 | 0.867714 | 0.720395 | 0.076* | |
H16B | 0.852306 | 0.925434 | 0.800595 | 0.076* | |
O17 | 0.1410 (5) | −0.5145 (5) | 0.4118 (2) | 0.1028 (14) | |
H17A | 0.260734 | −0.502696 | 0.416939 | 0.154* | |
H17B | 0.107064 | −0.525946 | 0.361789 | 0.154* | |
N1 | 0.6377 (3) | −0.2270 (2) | 0.07737 (13) | 0.0208 (4) | |
H1A | 0.584140 | −0.279830 | 0.027787 | 0.025* | |
H1B | 0.555410 | −0.246730 | 0.111117 | 0.025* | |
N2 | 0.1225 (4) | −0.2760 (2) | 0.55083 (15) | 0.0293 (5) | |
H2A | 0.029846 | −0.300628 | 0.579215 | 0.035* | |
H2B | 0.099926 | −0.323508 | 0.498405 | 0.035* | |
C1 | 0.8841 (5) | 0.1894 (4) | −0.04009 (19) | 0.0322 (7) | |
C2 | 0.7584 (4) | 0.4019 (3) | 0.09098 (14) | 0.0162 (5) | |
C3 | 0.6059 (4) | 0.2843 (3) | 0.22040 (15) | 0.0179 (5) | |
C4 | 0.6618 (3) | 0.1819 (3) | 0.14981 (14) | 0.0158 (5) | |
C5 | 0.7369 (3) | 0.2369 (3) | 0.08828 (14) | 0.0157 (5) | |
C6 | 0.7824 (4) | 0.1368 (3) | 0.02302 (15) | 0.0190 (5) | |
C7 | 0.7446 (4) | −0.0166 (3) | 0.01857 (15) | 0.0196 (5) | |
H7A | 0.770117 | −0.083545 | −0.025813 | 0.024* | |
C8 | 0.6690 (4) | −0.0699 (3) | 0.08004 (15) | 0.0174 (5) | |
C9 | 0.6324 (4) | 0.0295 (3) | 0.14634 (15) | 0.0181 (5) | |
H9A | 0.587864 | −0.005792 | 0.188749 | 0.022* | |
C10 | 0.3739 (4) | 0.1496 (3) | 0.44142 (15) | 0.0208 (5) | |
C11 | 0.3499 (4) | 0.3586 (3) | 0.59759 (14) | 0.0175 (5) | |
C12 | 0.2152 (4) | 0.2219 (3) | 0.72843 (15) | 0.0171 (5) | |
C13 | 0.2154 (3) | 0.1308 (3) | 0.64504 (14) | 0.0161 (5) | |
C14 | 0.2900 (3) | 0.1916 (3) | 0.58424 (14) | 0.0147 (5) | |
C15 | 0.2950 (4) | 0.0952 (3) | 0.51016 (14) | 0.0169 (5) | |
C16 | 0.2331 (4) | −0.0590 (3) | 0.49859 (15) | 0.0203 (5) | |
H16C | 0.237880 | −0.122937 | 0.449427 | 0.024* | |
C17 | 0.1647 (4) | −0.1175 (3) | 0.55947 (16) | 0.0200 (5) | |
C18 | 0.1518 (4) | −0.0222 (3) | 0.63174 (16) | 0.0192 (5) | |
H18A | 0.100108 | −0.061119 | 0.671735 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.03205 (18) | 0.01748 (15) | 0.01903 (15) | 0.00976 (12) | 0.00861 (12) | 0.00922 (11) |
Zn2 | 0.01967 (15) | 0.01773 (15) | 0.02243 (16) | 0.00263 (11) | −0.00079 (11) | 0.00531 (11) |
Zn3 | 0.03631 (18) | 0.01121 (14) | 0.01584 (15) | 0.00254 (12) | 0.00554 (12) | 0.00443 (11) |
O1 | 0.086 (2) | 0.074 (2) | 0.0270 (13) | 0.0262 (16) | 0.0323 (13) | 0.0186 (13) |
O2 | 0.0703 (18) | 0.0321 (13) | 0.0748 (19) | 0.0152 (12) | 0.0513 (15) | 0.0308 (13) |
O3 | 0.0332 (11) | 0.0167 (9) | 0.0243 (10) | 0.0090 (8) | −0.0006 (8) | 0.0092 (7) |
O4 | 0.0237 (9) | 0.0165 (8) | 0.0231 (9) | 0.0012 (7) | −0.0003 (7) | 0.0064 (7) |
O5 | 0.0432 (12) | 0.0234 (10) | 0.0286 (11) | 0.0193 (9) | 0.0117 (9) | 0.0085 (8) |
O6 | 0.0572 (14) | 0.0271 (10) | 0.0138 (9) | 0.0196 (10) | 0.0066 (9) | 0.0050 (8) |
O7 | 0.0542 (14) | 0.0277 (11) | 0.0174 (10) | 0.0010 (10) | 0.0066 (9) | 0.0025 (8) |
O8 | 0.0508 (13) | 0.0167 (9) | 0.0258 (10) | 0.0031 (9) | 0.0180 (9) | 0.0068 (8) |
O9 | 0.0320 (11) | 0.0123 (8) | 0.0318 (11) | 0.0047 (7) | −0.0004 (8) | 0.0076 (8) |
O10 | 0.0288 (10) | 0.0242 (10) | 0.0227 (10) | −0.0088 (8) | −0.0047 (8) | 0.0092 (8) |
O11 | 0.0244 (10) | 0.0245 (9) | 0.0213 (9) | 0.0003 (8) | 0.0083 (7) | 0.0050 (7) |
O12 | 0.0264 (10) | 0.0285 (10) | 0.0219 (10) | −0.0066 (8) | 0.0046 (8) | 0.0002 (8) |
O13 | 0.0332 (11) | 0.0373 (12) | 0.0229 (10) | 0.0107 (9) | 0.0000 (8) | 0.0071 (9) |
O14 | 0.0242 (10) | 0.0246 (10) | 0.0412 (12) | −0.0012 (8) | −0.0053 (9) | 0.0105 (9) |
O15 | 0.0375 (13) | 0.0299 (12) | 0.0576 (16) | 0.0180 (10) | −0.0134 (11) | −0.0091 (11) |
O16 | 0.0674 (18) | 0.0275 (12) | 0.0514 (16) | 0.0003 (11) | −0.0100 (13) | 0.0125 (11) |
O17 | 0.068 (2) | 0.160 (4) | 0.074 (3) | 0.001 (3) | 0.015 (2) | 0.027 (3) |
N1 | 0.0315 (12) | 0.0102 (9) | 0.0203 (11) | 0.0030 (8) | 0.0000 (9) | 0.0049 (8) |
N2 | 0.0428 (15) | 0.0104 (10) | 0.0293 (13) | −0.0024 (9) | −0.0100 (11) | 0.0055 (9) |
C1 | 0.0409 (17) | 0.0367 (16) | 0.0387 (17) | 0.0278 (14) | 0.0240 (14) | 0.0275 (14) |
C2 | 0.0223 (12) | 0.0130 (11) | 0.0155 (11) | 0.0037 (9) | 0.0057 (9) | 0.0067 (9) |
C3 | 0.0230 (13) | 0.0125 (11) | 0.0187 (12) | 0.0019 (9) | 0.0062 (10) | 0.0038 (9) |
C4 | 0.0214 (12) | 0.0124 (11) | 0.0145 (11) | 0.0047 (9) | 0.0021 (9) | 0.0041 (9) |
C5 | 0.0195 (12) | 0.0124 (11) | 0.0168 (11) | 0.0037 (9) | 0.0015 (9) | 0.0072 (9) |
C6 | 0.0260 (13) | 0.0182 (12) | 0.0180 (12) | 0.0101 (10) | 0.0066 (10) | 0.0097 (10) |
C7 | 0.0307 (14) | 0.0154 (11) | 0.0153 (11) | 0.0104 (10) | 0.0055 (10) | 0.0036 (9) |
C8 | 0.0221 (12) | 0.0111 (11) | 0.0196 (12) | 0.0049 (9) | 0.0000 (10) | 0.0054 (9) |
C9 | 0.0264 (13) | 0.0148 (11) | 0.0158 (11) | 0.0052 (10) | 0.0059 (10) | 0.0073 (9) |
C10 | 0.0264 (14) | 0.0210 (12) | 0.0177 (12) | 0.0089 (10) | 0.0036 (10) | 0.0071 (10) |
C11 | 0.0275 (13) | 0.0111 (11) | 0.0132 (11) | 0.0006 (9) | 0.0031 (10) | 0.0039 (9) |
C12 | 0.0234 (13) | 0.0145 (11) | 0.0163 (12) | 0.0055 (9) | 0.0033 (9) | 0.0084 (9) |
C13 | 0.0185 (12) | 0.0137 (11) | 0.0170 (12) | 0.0030 (9) | 0.0015 (9) | 0.0061 (9) |
C14 | 0.0183 (12) | 0.0112 (10) | 0.0157 (11) | 0.0036 (9) | 0.0003 (9) | 0.0060 (9) |
C15 | 0.0213 (12) | 0.0146 (11) | 0.0152 (11) | 0.0038 (9) | 0.0005 (9) | 0.0051 (9) |
C16 | 0.0276 (14) | 0.0142 (11) | 0.0176 (12) | 0.0056 (10) | −0.0013 (10) | 0.0015 (9) |
C17 | 0.0226 (13) | 0.0106 (11) | 0.0250 (13) | −0.0002 (9) | −0.0054 (10) | 0.0068 (10) |
C18 | 0.0212 (12) | 0.0155 (11) | 0.0216 (12) | 0.0000 (9) | 0.0003 (10) | 0.0092 (10) |
Geometric parameters (Å, º) top
Zn1—O4 | 2.0235 (18) | O15—H15B | 0.8500 |
Zn1—O11i | 2.0350 (19) | O16—H16A | 0.8500 |
Zn1—O2ii | 2.046 (2) | O16—H16B | 0.8501 |
Zn1—N1iii | 2.074 (2) | O17—H17A | 0.8501 |
Zn1—O1ii | 2.439 (3) | O17—H17B | 0.8501 |
Zn1—C1ii | 2.580 (3) | N1—C8 | 1.434 (3) |
Zn2—O14 | 2.039 (2) | N1—H1A | 0.9000 |
Zn2—O12 | 2.0458 (19) | N1—H1B | 0.9000 |
Zn2—O10 | 2.0630 (19) | N2—C17 | 1.430 (3) |
Zn2—O5i | 2.0936 (19) | N2—H2A | 0.9000 |
Zn2—O15 | 2.097 (2) | N2—H2B | 0.9001 |
Zn2—O13 | 2.141 (2) | C1—C6 | 1.499 (4) |
Zn3—O6 | 1.9248 (19) | C2—C5 | 1.509 (3) |
Zn3—O8 | 1.940 (2) | C3—C4 | 1.506 (3) |
Zn3—O9i | 1.9926 (18) | C4—C9 | 1.388 (3) |
Zn3—N2iv | 2.107 (2) | C4—C5 | 1.396 (3) |
O1—C1 | 1.221 (4) | C5—C6 | 1.399 (3) |
O2—C1 | 1.263 (4) | C6—C7 | 1.395 (3) |
O3—C2 | 1.238 (3) | C7—C8 | 1.389 (3) |
O4—C2 | 1.275 (3) | C7—H7A | 0.9300 |
O5—C3 | 1.232 (3) | C8—C9 | 1.382 (3) |
O6—C3 | 1.259 (3) | C9—H9A | 0.9300 |
O7—C10 | 1.232 (3) | C10—C15 | 1.515 (3) |
O8—C10 | 1.277 (3) | C11—C14 | 1.506 (3) |
O9—C11 | 1.261 (3) | C12—C13 | 1.500 (3) |
O10—C11 | 1.253 (3) | C13—C18 | 1.387 (3) |
O11—C12 | 1.267 (3) | C13—C14 | 1.410 (3) |
O12—C12 | 1.240 (3) | C14—C15 | 1.399 (3) |
O13—H13A | 0.8499 | C15—C16 | 1.398 (3) |
O13—H13B | 0.8501 | C16—C17 | 1.382 (4) |
O14—H14A | 0.8501 | C16—H16C | 0.9300 |
O14—H14B | 0.8499 | C17—C18 | 1.383 (4) |
O15—H15A | 0.8499 | C18—H18A | 0.9300 |
| | | |
O4—Zn1—O11i | 96.74 (8) | C17—N2—Zn3iv | 111.86 (17) |
O4—Zn1—O2ii | 97.91 (8) | C17—N2—H2A | 110.9 |
O11i—Zn1—O2ii | 136.57 (10) | Zn3iv—N2—H2A | 102.9 |
O4—Zn1—N1iii | 130.45 (8) | C17—N2—H2B | 110.1 |
O11i—Zn1—N1iii | 102.11 (8) | Zn3iv—N2—H2B | 106.4 |
O2ii—Zn1—N1iii | 98.81 (10) | H2A—N2—H2B | 114.4 |
O4—Zn1—O1ii | 126.91 (9) | O1—C1—O2 | 120.6 (3) |
O11i—Zn1—O1ii | 82.03 (8) | O1—C1—C6 | 121.3 (3) |
O2ii—Zn1—O1ii | 56.69 (10) | O2—C1—C6 | 117.9 (3) |
N1iii—Zn1—O1ii | 101.02 (9) | O1—C1—Zn1ii | 69.56 (19) |
O4—Zn1—C1ii | 116.58 (8) | O2—C1—Zn1ii | 51.39 (15) |
O11i—Zn1—C1ii | 109.55 (10) | C6—C1—Zn1ii | 165.5 (2) |
O2ii—Zn1—C1ii | 28.83 (11) | O3—C2—O4 | 122.4 (2) |
N1iii—Zn1—C1ii | 99.45 (9) | O3—C2—C5 | 119.3 (2) |
O1ii—Zn1—C1ii | 27.97 (10) | O4—C2—C5 | 118.3 (2) |
O14—Zn2—O12 | 173.84 (8) | O5—C3—O6 | 127.7 (2) |
O14—Zn2—O10 | 93.57 (8) | O5—C3—C4 | 117.5 (2) |
O12—Zn2—O10 | 90.42 (8) | O6—C3—C4 | 114.8 (2) |
O14—Zn2—O5i | 92.74 (9) | C9—C4—C5 | 120.4 (2) |
O12—Zn2—O5i | 82.40 (8) | C9—C4—C3 | 118.1 (2) |
O10—Zn2—O5i | 92.22 (8) | C5—C4—C3 | 121.4 (2) |
O14—Zn2—O15 | 94.18 (9) | C4—C5—C6 | 119.3 (2) |
O12—Zn2—O15 | 90.32 (9) | C4—C5—C2 | 119.6 (2) |
O10—Zn2—O15 | 92.70 (9) | C6—C5—C2 | 121.0 (2) |
O5i—Zn2—O15 | 171.24 (10) | C7—C6—C5 | 119.7 (2) |
O14—Zn2—O13 | 90.83 (9) | C7—C6—C1 | 118.1 (2) |
O12—Zn2—O13 | 84.85 (8) | C5—C6—C1 | 122.0 (2) |
O10—Zn2—O13 | 173.72 (8) | C8—C7—C6 | 120.4 (2) |
O5i—Zn2—O13 | 83.08 (8) | C8—C7—H7A | 119.8 |
O15—Zn2—O13 | 91.44 (9) | C6—C7—H7A | 119.8 |
O6—Zn3—O8 | 121.43 (9) | C9—C8—C7 | 119.9 (2) |
O6—Zn3—O9i | 113.23 (9) | C9—C8—N1 | 119.5 (2) |
O8—Zn3—O9i | 119.52 (8) | C7—C8—N1 | 120.5 (2) |
O6—Zn3—N2iv | 97.68 (9) | C8—C9—C4 | 120.2 (2) |
O8—Zn3—N2iv | 99.62 (10) | C8—C9—H9A | 119.9 |
O9i—Zn3—N2iv | 96.77 (8) | C4—C9—H9A | 119.9 |
C1—O1—Zn1ii | 82.5 (2) | O7—C10—O8 | 124.7 (2) |
C1—O2—Zn1ii | 99.8 (2) | O7—C10—C15 | 119.7 (2) |
C2—O4—Zn1 | 104.30 (15) | O8—C10—C15 | 115.6 (2) |
C3—O5—Zn2i | 149.38 (18) | O10—C11—O9 | 121.3 (2) |
C3—O6—Zn3 | 135.29 (17) | O10—C11—C14 | 121.8 (2) |
C10—O8—Zn3 | 121.02 (17) | O9—C11—C14 | 116.9 (2) |
C11—O9—Zn3i | 106.62 (16) | O12—C12—O11 | 121.2 (2) |
C11—O10—Zn2 | 124.64 (16) | O12—C12—C13 | 120.6 (2) |
C12—O11—Zn1i | 109.97 (16) | O11—C12—C13 | 118.0 (2) |
C12—O12—Zn2 | 145.03 (18) | C18—C13—C14 | 120.3 (2) |
Zn2—O13—H13A | 125.2 | C18—C13—C12 | 116.2 (2) |
Zn2—O13—H13B | 112.2 | C14—C13—C12 | 123.3 (2) |
H13A—O13—H13B | 97.3 | C15—C14—C13 | 118.7 (2) |
Zn2—O14—H14A | 120.1 | C15—C14—C11 | 121.1 (2) |
Zn2—O14—H14B | 120.0 | C13—C14—C11 | 120.1 (2) |
H14A—O14—H14B | 103.4 | C16—C15—C14 | 119.9 (2) |
Zn2—O15—H15A | 128.7 | C16—C15—C10 | 117.4 (2) |
Zn2—O15—H15B | 135.4 | C14—C15—C10 | 122.6 (2) |
H15A—O15—H15B | 95.8 | C17—C16—C15 | 120.7 (2) |
H16A—O16—H16B | 114.8 | C17—C16—H16C | 119.7 |
H17A—O17—H17B | 104.5 | C15—C16—H16C | 119.7 |
C8—N1—Zn1v | 115.05 (16) | C16—C17—C18 | 119.7 (2) |
C8—N1—H1A | 109.9 | C16—C17—N2 | 120.5 (2) |
Zn1v—N1—H1A | 112.4 | C18—C17—N2 | 119.6 (2) |
C8—N1—H1B | 109.3 | C17—C18—C13 | 120.5 (2) |
Zn1v—N1—H1B | 103.0 | C17—C18—H18A | 119.7 |
H1A—N1—H1B | 106.7 | C13—C18—H18A | 119.7 |
| | | |
Zn1ii—O1—C1—O2 | 6.2 (3) | C3—C4—C9—C8 | 175.4 (2) |
Zn1ii—O1—C1—C6 | −169.4 (3) | Zn3—O8—C10—O7 | −23.9 (4) |
Zn1ii—O2—C1—O1 | −7.5 (4) | Zn3—O8—C10—C15 | 154.11 (18) |
Zn1ii—O2—C1—C6 | 168.3 (2) | Zn2—O10—C11—O9 | 114.2 (2) |
Zn1—O4—C2—O3 | −2.8 (3) | Zn2—O10—C11—C14 | −62.8 (3) |
Zn1—O4—C2—C5 | 178.49 (17) | Zn3i—O9—C11—O10 | 2.0 (3) |
Zn2i—O5—C3—O6 | 3.0 (6) | Zn3i—O9—C11—C14 | 179.13 (17) |
Zn2i—O5—C3—C4 | −178.3 (3) | Zn2—O12—C12—O11 | −172.8 (2) |
Zn3—O6—C3—O5 | −9.9 (5) | Zn2—O12—C12—C13 | 12.5 (5) |
Zn3—O6—C3—C4 | 171.37 (19) | Zn1i—O11—C12—O12 | −4.6 (3) |
O5—C3—C4—C9 | −135.2 (3) | Zn1i—O11—C12—C13 | 170.36 (16) |
O6—C3—C4—C9 | 43.7 (3) | O12—C12—C13—C18 | 132.6 (3) |
O5—C3—C4—C5 | 43.2 (4) | O11—C12—C13—C18 | −42.3 (3) |
O6—C3—C4—C5 | −137.9 (3) | O12—C12—C13—C14 | −42.0 (4) |
C9—C4—C5—C6 | 0.0 (4) | O11—C12—C13—C14 | 143.0 (2) |
C3—C4—C5—C6 | −178.5 (2) | C18—C13—C14—C15 | 1.2 (4) |
C9—C4—C5—C2 | 176.8 (2) | C12—C13—C14—C15 | 175.7 (2) |
C3—C4—C5—C2 | −1.6 (4) | C18—C13—C14—C11 | 177.0 (2) |
O3—C2—C5—C4 | −100.9 (3) | C12—C13—C14—C11 | −8.6 (4) |
O4—C2—C5—C4 | 77.9 (3) | O10—C11—C14—C15 | −99.9 (3) |
O3—C2—C5—C6 | 76.0 (3) | O9—C11—C14—C15 | 83.0 (3) |
O4—C2—C5—C6 | −105.3 (3) | O10—C11—C14—C13 | 84.4 (3) |
C4—C5—C6—C7 | 2.8 (4) | O9—C11—C14—C13 | −92.7 (3) |
C2—C5—C6—C7 | −174.0 (2) | C13—C14—C15—C16 | −2.3 (4) |
C4—C5—C6—C1 | −172.7 (2) | C11—C14—C15—C16 | −178.0 (2) |
C2—C5—C6—C1 | 10.5 (4) | C13—C14—C15—C10 | −179.5 (2) |
O1—C1—C6—C7 | 27.3 (4) | C11—C14—C15—C10 | 4.8 (4) |
O2—C1—C6—C7 | −148.4 (3) | O7—C10—C15—C16 | 8.6 (4) |
Zn1ii—C1—C6—C7 | −109.1 (8) | O8—C10—C15—C16 | −169.5 (2) |
O1—C1—C6—C5 | −157.2 (3) | O7—C10—C15—C14 | −174.1 (3) |
O2—C1—C6—C5 | 27.1 (4) | O8—C10—C15—C14 | 7.7 (4) |
Zn1ii—C1—C6—C5 | 66.5 (8) | C14—C15—C16—C17 | 0.7 (4) |
C5—C6—C7—C8 | −2.5 (4) | C10—C15—C16—C17 | 178.0 (2) |
C1—C6—C7—C8 | 173.1 (3) | C15—C16—C17—C18 | 2.1 (4) |
C6—C7—C8—C9 | −0.5 (4) | C15—C16—C17—N2 | −172.6 (2) |
C6—C7—C8—N1 | −177.2 (2) | Zn3iv—N2—C17—C16 | 94.7 (3) |
Zn1v—N1—C8—C9 | −93.3 (3) | Zn3iv—N2—C17—C18 | −80.0 (3) |
Zn1v—N1—C8—C7 | 83.5 (3) | C16—C17—C18—C13 | −3.1 (4) |
C7—C8—C9—C4 | 3.3 (4) | N2—C17—C18—C13 | 171.6 (2) |
N1—C8—C9—C4 | −180.0 (2) | C14—C13—C18—C17 | 1.5 (4) |
C5—C4—C9—C8 | −3.0 (4) | C12—C13—C18—C17 | −173.3 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z; (iii) x, y+1, z; (iv) −x+1, −y, −z+1; (v) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13A···O2vi | 0.85 | 2.58 | 3.358 (4) | 154 |
O13—H13B···O3i | 0.85 | 2.17 | 2.964 (3) | 156 |
O14—H14A···O4vi | 0.85 | 1.90 | 2.709 (3) | 157 |
O14—H14B···O16 | 0.85 | 1.82 | 2.661 (3) | 170 |
O15—H15A···O7iv | 0.85 | 2.04 | 2.840 (3) | 156 |
O15—H15B···O11vii | 0.85 | 1.92 | 2.762 (3) | 168 |
O16—H16A···O7i | 0.85 | 2.06 | 2.885 (3) | 164 |
O16—H16B···O1viii | 0.85 | 2.04 | 2.878 (4) | 171 |
O17—H17A···O10iv | 0.85 | 2.05 | 2.774 (4) | 143 |
O17—H17B···O14iv | 0.85 | 1.92 | 2.717 (4) | 155 |
N1—H1A···O3ix | 0.90 | 2.16 | 2.969 (3) | 150 |
N1—H1B···O13iv | 0.90 | 2.41 | 3.141 (3) | 139 |
N2—H2A···O17x | 0.90 | 2.00 | 2.736 (5) | 138 |
N2—H2B···O17 | 0.90 | 2.14 | 2.919 (5) | 145 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (vi) −x+2, −y+1, −z+1; (vii) x+1, y, z; (viii) x, y+1, z+1; (ix) −x+1, −y, −z; (x) −x, −y−1, −z+1. |