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Two new metal–organic frameworks (MOFs), namely, three-dimensional poly[diaquabis{μ2-1,4-bis[(2-methyl-1H-imidazol-1-yl)methyl]benzene}bis(μ2-glutarato)dinickel(II)] monohydrate], {[Ni2(C5H6O4)2(C16H18N4)2(H2O)2]·H2O}n or {[Ni2(Glu)2(1,4-mbix)2(H2O)2]·H2O}n, (I), and two-dimensional poly[[{μ2-1,4-bis[(2-methyl-1H-imidazol-1-yl)methyl]benzene}(μ2-glutarato)zinc(II)] tetrahydrate], {[Zn(C5H6O4)(C16H18N4)]·4H2O}n or {[Zn(Glu)(1,4-mbix)]·4H2O}n (II), have been synthesized hydrothermally using glutarate (Glu2−) mixed with 1,4-bis[(2-methyl-1H-imidazol-1-yl)methyl]benzene (1,4-mbix), and characterized by single-crystal X-ray diffraction, IR and UV–Vis spectroscopy, powder X-ray diffraction, and thermogravimetric and photoluminescence analyses. NiII MOF (I) shows a 4-connected 3D framework with point symbol 66, but is not a typical dia network. ZnII MOF (II) displays a two-dimensional 44-sql network with one-dimensional water chains penetrating the grids along the c direction. The solid-state photoluminescence analysis of (II) was performed at room temperature and the MOF exhibits highly selective sensing toward Fe3+ and Cr2O72− ions in aqueous solution.
Supporting information
CCDC references: 1951833; 1951832
For both structures, data collection: SMART (Bruker, 2016); cell refinement: SMART (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2016); software used to prepare material for publication: SHELXTL (Bruker, 2016).
Poly[diaquabis{µ
2-1,4-bis[(2-methyl-1
H-imidazol-1-yl)methyl]benzene}bis(µ
2-glutarato)dinickel(II)] monohydrate] (1)
top
Crystal data top
[Ni2(C5H6O4)2(C16H18N4)2(H2O)2]·H2O | F(000) = 2024 |
Mr = 964.35 | Dx = 1.484 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.188 (1) Å | Cell parameters from 9972 reflections |
b = 15.6516 (10) Å | θ = 2.2–26.4° |
c = 22.7466 (19) Å | µ = 0.94 mm−1 |
β = 95.989 (3)° | T = 153 K |
V = 4315.5 (6) Å3 | Block, green |
Z = 4 | 0.20 × 0.20 × 0.20 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | Rint = 0.041 |
phi and ω scans | θmax = 26.4°, θmin = 2.2° |
31530 measured reflections | h = −15→15 |
4437 independent reflections | k = −19→19 |
3873 reflections with I > 2σ(I) | l = −28→28 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0433P)2 + 11.7921P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4437 reflections | Δρmax = 0.92 e Å−3 |
287 parameters | Δρmin = −0.49 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 | |
C1 | 0.24387 (18) | 0.06356 (13) | 0.22946 (10) | 0.0169 (4) | |
C2 | 0.1795 (2) | 0.03640 (15) | 0.17219 (10) | 0.0231 (5) | |
H2A | 0.2317 | 0.0253 | 0.1425 | 0.028* | |
H2B | 0.1306 | 0.0839 | 0.1573 | 0.028* | |
C3 | 0.3905 (2) | 0.45638 (14) | 0.32142 (10) | 0.0193 (5) | |
H3A | 0.4437 | 0.4678 | 0.2923 | 0.023* | |
H3B | 0.4332 | 0.4437 | 0.3599 | 0.023* | |
C4 | 0.3214 (2) | 0.37859 (15) | 0.30151 (12) | 0.0284 (6) | |
H4A | 0.2985 | 0.3837 | 0.2586 | 0.034* | |
H4B | 0.2536 | 0.3789 | 0.3220 | 0.034* | |
C5 | 0.3795 (2) | 0.29295 (14) | 0.31307 (10) | 0.0201 (5) | |
C6 | 0.1355 (2) | 0.18932 (18) | 0.39624 (13) | 0.0321 (6) | |
H6A | 0.1577 | 0.2127 | 0.3593 | 0.048* | |
H6B | 0.1039 | 0.2350 | 0.4187 | 0.048* | |
H6C | 0.0803 | 0.1444 | 0.3872 | 0.048* | |
C7 | 0.2338 (2) | 0.15268 (15) | 0.43199 (11) | 0.0234 (5) | |
C8 | 0.3420 (2) | 0.10487 (17) | 0.50810 (12) | 0.0305 (6) | |
H8 | 0.3707 | 0.0892 | 0.5470 | 0.037* | |
C9 | 0.3921 (2) | 0.09672 (16) | 0.45896 (11) | 0.0259 (5) | |
H9 | 0.4635 | 0.0732 | 0.4572 | 0.031* | |
C10 | 0.1480 (2) | 0.14476 (17) | 0.52737 (11) | 0.0276 (5) | |
H10A | 0.1070 | 0.1989 | 0.5197 | 0.033* | |
H10B | 0.1774 | 0.1437 | 0.5696 | 0.033* | |
C11 | 0.0705 (2) | 0.06963 (16) | 0.51408 (10) | 0.0220 (5) | |
C12 | −0.0394 (2) | 0.08282 (16) | 0.49313 (11) | 0.0252 (5) | |
H12 | −0.0671 | 0.1394 | 0.4883 | 0.030* | |
C13 | −0.1091 (2) | 0.01379 (17) | 0.47920 (10) | 0.0248 (5) | |
H13 | −0.1840 | 0.0237 | 0.4649 | 0.030* | |
C14 | 0.1837 (2) | −0.05222 (15) | 0.37851 (11) | 0.0248 (5) | |
H14A | 0.1930 | −0.0418 | 0.4212 | 0.037* | |
H14B | 0.1303 | −0.0985 | 0.3696 | 0.037* | |
H14C | 0.1567 | −0.0001 | 0.3579 | 0.037* | |
C15 | 0.29122 (18) | −0.07686 (14) | 0.35848 (9) | 0.0166 (4) | |
C16 | 0.45185 (19) | −0.07636 (15) | 0.32541 (10) | 0.0214 (5) | |
H16 | 0.5177 | −0.0565 | 0.3111 | 0.026* | |
C17 | 0.4265 (2) | −0.15921 (16) | 0.33369 (11) | 0.0246 (5) | |
H17 | 0.4700 | −0.2077 | 0.3263 | 0.029* | |
C18 | 0.2633 (2) | −0.23363 (14) | 0.37256 (10) | 0.0241 (5) | |
H18A | 0.2987 | −0.2858 | 0.3588 | 0.029* | |
H18B | 0.1874 | −0.2311 | 0.3524 | 0.029* | |
C19 | 0.25740 (19) | −0.24064 (14) | 0.43884 (10) | 0.0188 (5) | |
C20 | 0.3251 (2) | −0.19379 (15) | 0.48008 (11) | 0.0234 (5) | |
H20 | 0.3771 | −0.1549 | 0.4669 | 0.028* | |
C21 | 0.1823 (2) | −0.29695 (15) | 0.45978 (11) | 0.0229 (5) | |
H21 | 0.1352 | −0.3296 | 0.4325 | 0.027* | |
N1 | 0.32406 (17) | 0.12776 (13) | 0.41059 (9) | 0.0233 (4) | |
N2 | 0.23899 (19) | 0.14107 (14) | 0.49083 (9) | 0.0278 (5) | |
N3 | 0.36720 (15) | −0.02482 (11) | 0.34099 (8) | 0.0160 (4) | |
N4 | 0.32452 (16) | −0.15905 (11) | 0.35517 (8) | 0.0184 (4) | |
Ni1 | 0.35165 (2) | 0.10492 (2) | 0.32341 (2) | 0.01340 (9) | |
O1 | 0.34783 (13) | 0.07068 (10) | 0.23281 (7) | 0.0193 (3) | |
O2 | 0.19381 (12) | 0.07799 (10) | 0.27437 (7) | 0.0183 (3) | |
O3 | 0.32132 (14) | 0.22832 (10) | 0.29864 (8) | 0.0268 (4) | |
O4 | 0.47570 (15) | 0.29124 (11) | 0.33788 (9) | 0.0317 (4) | |
O5 | 0.51657 (12) | 0.12815 (10) | 0.34470 (7) | 0.0165 (3) | |
H5A | 0.5126 | 0.1826 | 0.3445 | 0.025* | |
H5B | 0.5607 | 0.1072 | 0.3215 | 0.025* | |
O6 | 0.0000 | 0.17771 (16) | 0.2500 | 0.0360 (7) | |
H6D | 0.0536 | 0.1440 | 0.2591 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0210 (11) | 0.0091 (10) | 0.0196 (11) | −0.0029 (8) | −0.0021 (9) | 0.0035 (8) |
C2 | 0.0283 (12) | 0.0201 (12) | 0.0195 (12) | −0.0082 (9) | −0.0045 (9) | 0.0027 (9) |
C3 | 0.0225 (11) | 0.0146 (11) | 0.0200 (11) | 0.0029 (9) | −0.0018 (9) | 0.0014 (8) |
C4 | 0.0316 (14) | 0.0163 (11) | 0.0339 (14) | 0.0012 (10) | −0.0130 (11) | 0.0029 (10) |
C5 | 0.0251 (12) | 0.0141 (11) | 0.0204 (11) | 0.0000 (9) | −0.0015 (9) | 0.0014 (8) |
C6 | 0.0286 (14) | 0.0306 (14) | 0.0364 (15) | 0.0071 (11) | −0.0001 (11) | −0.0002 (11) |
C7 | 0.0301 (13) | 0.0188 (11) | 0.0228 (12) | −0.0083 (9) | 0.0093 (10) | −0.0063 (9) |
C8 | 0.0297 (14) | 0.0368 (15) | 0.0242 (13) | −0.0046 (11) | −0.0009 (10) | 0.0021 (11) |
C9 | 0.0223 (12) | 0.0289 (13) | 0.0252 (13) | 0.0013 (10) | −0.0040 (10) | −0.0031 (10) |
C10 | 0.0306 (13) | 0.0326 (14) | 0.0216 (12) | −0.0087 (11) | 0.0120 (10) | −0.0081 (10) |
C11 | 0.0262 (12) | 0.0274 (12) | 0.0139 (11) | −0.0041 (10) | 0.0099 (9) | −0.0033 (9) |
C12 | 0.0297 (13) | 0.0254 (12) | 0.0221 (12) | 0.0007 (10) | 0.0109 (10) | 0.0008 (10) |
C13 | 0.0224 (12) | 0.0336 (13) | 0.0195 (12) | −0.0005 (10) | 0.0075 (9) | −0.0003 (10) |
C14 | 0.0249 (12) | 0.0200 (11) | 0.0316 (13) | −0.0040 (9) | 0.0136 (10) | 0.0011 (10) |
C15 | 0.0221 (11) | 0.0135 (10) | 0.0139 (10) | −0.0017 (8) | 0.0003 (8) | −0.0005 (8) |
C16 | 0.0197 (11) | 0.0215 (11) | 0.0234 (12) | 0.0026 (9) | 0.0040 (9) | 0.0016 (9) |
C17 | 0.0280 (13) | 0.0217 (12) | 0.0240 (12) | 0.0073 (10) | 0.0024 (10) | 0.0012 (9) |
C18 | 0.0382 (14) | 0.0132 (10) | 0.0201 (12) | −0.0078 (10) | −0.0002 (10) | 0.0020 (9) |
C19 | 0.0253 (12) | 0.0114 (10) | 0.0183 (11) | −0.0015 (8) | −0.0043 (9) | 0.0032 (8) |
C20 | 0.0274 (13) | 0.0174 (11) | 0.0241 (12) | −0.0087 (9) | −0.0040 (10) | 0.0050 (9) |
C21 | 0.0281 (13) | 0.0176 (11) | 0.0208 (12) | −0.0078 (9) | −0.0077 (9) | 0.0028 (9) |
N1 | 0.0243 (10) | 0.0220 (10) | 0.0238 (10) | −0.0038 (8) | 0.0038 (8) | −0.0043 (8) |
N2 | 0.0329 (12) | 0.0278 (11) | 0.0243 (11) | −0.0084 (9) | 0.0111 (9) | −0.0084 (9) |
N3 | 0.0180 (9) | 0.0152 (9) | 0.0151 (9) | −0.0006 (7) | 0.0023 (7) | 0.0009 (7) |
N4 | 0.0260 (10) | 0.0123 (9) | 0.0166 (9) | −0.0022 (7) | 0.0004 (8) | 0.0017 (7) |
Ni1 | 0.01322 (15) | 0.01142 (15) | 0.01584 (15) | −0.00161 (10) | 0.00288 (10) | −0.00095 (10) |
O1 | 0.0186 (8) | 0.0211 (8) | 0.0182 (8) | −0.0024 (6) | 0.0027 (6) | 0.0024 (6) |
O2 | 0.0152 (8) | 0.0174 (8) | 0.0219 (8) | −0.0010 (6) | 0.0006 (6) | −0.0019 (6) |
O3 | 0.0259 (9) | 0.0140 (8) | 0.0378 (10) | −0.0021 (7) | −0.0104 (8) | 0.0013 (7) |
O4 | 0.0245 (9) | 0.0149 (8) | 0.0531 (12) | 0.0000 (7) | −0.0090 (8) | −0.0037 (8) |
O5 | 0.0161 (7) | 0.0156 (7) | 0.0182 (8) | 0.0004 (6) | 0.0030 (6) | −0.0032 (6) |
O6 | 0.0214 (13) | 0.0247 (13) | 0.0595 (19) | 0.000 | −0.0066 (12) | 0.000 |
Geometric parameters (Å, º) top
C1—O2 | 1.264 (3) | C12—H12 | 0.9500 |
C1—O1 | 1.266 (3) | C13—C11iii | 1.391 (4) |
C1—C2 | 1.510 (3) | C13—H13 | 0.9500 |
C1—Ni1 | 2.475 (2) | C14—C15 | 1.482 (3) |
C2—C3i | 1.531 (3) | C14—H14A | 0.9800 |
C2—H2A | 0.9900 | C14—H14B | 0.9800 |
C2—H2B | 0.9900 | C14—H14C | 0.9800 |
C3—C4 | 1.522 (3) | C15—N3 | 1.325 (3) |
C3—C2ii | 1.531 (3) | C15—N4 | 1.353 (3) |
C3—H3A | 0.9900 | C16—C17 | 1.351 (4) |
C3—H3B | 0.9900 | C16—N3 | 1.385 (3) |
C4—C5 | 1.526 (3) | C16—H16 | 0.9500 |
C4—H4A | 0.9900 | C17—N4 | 1.383 (3) |
C4—H4B | 0.9900 | C17—H17 | 0.9500 |
C5—O4 | 1.247 (3) | C18—N4 | 1.462 (3) |
C5—O3 | 1.259 (3) | C18—C19 | 1.521 (3) |
C6—C7 | 1.490 (4) | C18—H18A | 0.9900 |
C6—H6A | 0.9800 | C18—H18B | 0.9900 |
C6—H6B | 0.9800 | C19—C21 | 1.391 (3) |
C6—H6C | 0.9800 | C19—C20 | 1.392 (3) |
C7—N1 | 1.308 (3) | C20—C21iv | 1.388 (3) |
C7—N2 | 1.346 (3) | C20—H20 | 0.9500 |
C8—C9 | 1.334 (4) | C21—C20iv | 1.388 (3) |
C8—N2 | 1.396 (4) | C21—H21 | 0.9500 |
C8—H8 | 0.9500 | N1—Ni1 | 2.077 (2) |
C9—N1 | 1.394 (3) | N3—Ni1 | 2.0746 (18) |
C9—H9 | 0.9500 | Ni1—O3 | 2.0350 (16) |
C10—N2 | 1.454 (3) | Ni1—O5 | 2.0503 (15) |
C10—C11 | 1.519 (3) | Ni1—O1 | 2.1252 (16) |
C10—H10A | 0.9900 | Ni1—O2 | 2.1622 (15) |
C10—H10B | 0.9900 | O5—H5A | 0.8535 |
C11—C12 | 1.389 (4) | O5—H5B | 0.8559 |
C11—C13iii | 1.391 (4) | O6—H6D | 0.8484 |
C12—C13 | 1.390 (4) | | |
| | | |
O2—C1—O1 | 120.0 (2) | N3—C15—N4 | 110.2 (2) |
O2—C1—C2 | 119.8 (2) | N3—C15—C14 | 126.9 (2) |
O1—C1—C2 | 120.2 (2) | N4—C15—C14 | 123.0 (2) |
O2—C1—Ni1 | 60.84 (11) | C17—C16—N3 | 109.7 (2) |
O1—C1—Ni1 | 59.16 (11) | C17—C16—H16 | 125.2 |
C2—C1—Ni1 | 178.69 (17) | N3—C16—H16 | 125.2 |
C1—C2—C3i | 113.14 (19) | C16—C17—N4 | 105.9 (2) |
C1—C2—H2A | 109.0 | C16—C17—H17 | 127.0 |
C3i—C2—H2A | 109.0 | N4—C17—H17 | 127.0 |
C1—C2—H2B | 109.0 | N4—C18—C19 | 113.85 (19) |
C3i—C2—H2B | 109.0 | N4—C18—H18A | 108.8 |
H2A—C2—H2B | 107.8 | C19—C18—H18A | 108.8 |
C4—C3—C2ii | 112.7 (2) | N4—C18—H18B | 108.8 |
C4—C3—H3A | 109.0 | C19—C18—H18B | 108.8 |
C2ii—C3—H3A | 109.0 | H18A—C18—H18B | 107.7 |
C4—C3—H3B | 109.0 | C21—C19—C20 | 117.9 (2) |
C2ii—C3—H3B | 109.0 | C21—C19—C18 | 119.1 (2) |
H3A—C3—H3B | 107.8 | C20—C19—C18 | 122.9 (2) |
C3—C4—C5 | 114.7 (2) | C21iv—C20—C19 | 121.0 (2) |
C3—C4—H4A | 108.6 | C21iv—C20—H20 | 119.5 |
C5—C4—H4A | 108.6 | C19—C20—H20 | 119.5 |
C3—C4—H4B | 108.6 | C20iv—C21—C19 | 121.1 (2) |
C5—C4—H4B | 108.6 | C20iv—C21—H21 | 119.4 |
H4A—C4—H4B | 107.6 | C19—C21—H21 | 119.4 |
O4—C5—O3 | 125.3 (2) | C7—N1—C9 | 105.3 (2) |
O4—C5—C4 | 119.6 (2) | C7—N1—Ni1 | 129.26 (18) |
O3—C5—C4 | 114.9 (2) | C9—N1—Ni1 | 123.46 (17) |
C7—C6—H6A | 109.5 | C7—N2—C8 | 106.4 (2) |
C7—C6—H6B | 109.5 | C7—N2—C10 | 127.1 (2) |
H6A—C6—H6B | 109.5 | C8—N2—C10 | 124.9 (2) |
C7—C6—H6C | 109.5 | C15—N3—C16 | 106.35 (19) |
H6A—C6—H6C | 109.5 | C15—N3—Ni1 | 127.36 (15) |
H6B—C6—H6C | 109.5 | C16—N3—Ni1 | 125.20 (15) |
N1—C7—N2 | 112.1 (2) | C15—N4—C17 | 107.90 (19) |
N1—C7—C6 | 124.8 (2) | C15—N4—C18 | 125.4 (2) |
N2—C7—C6 | 123.1 (2) | C17—N4—C18 | 126.7 (2) |
C9—C8—N2 | 106.2 (2) | O3—Ni1—O5 | 92.43 (7) |
C9—C8—H8 | 126.9 | O3—Ni1—N3 | 173.08 (7) |
N2—C8—H8 | 126.9 | O5—Ni1—N3 | 93.47 (7) |
C8—C9—N1 | 110.0 (2) | O3—Ni1—N1 | 93.34 (8) |
C8—C9—H9 | 125.0 | O5—Ni1—N1 | 89.79 (7) |
N1—C9—H9 | 125.0 | N3—Ni1—N1 | 90.29 (8) |
N2—C10—C11 | 110.55 (19) | O3—Ni1—O1 | 89.19 (7) |
N2—C10—H10A | 109.5 | O5—Ni1—O1 | 101.27 (6) |
C11—C10—H10A | 109.5 | N3—Ni1—O1 | 86.12 (7) |
N2—C10—H10B | 109.5 | N1—Ni1—O1 | 168.54 (7) |
C11—C10—H10B | 109.5 | O3—Ni1—O2 | 85.18 (6) |
H10A—C10—H10B | 108.1 | O5—Ni1—O2 | 162.55 (6) |
C12—C11—C13iii | 118.7 (2) | N3—Ni1—O2 | 88.11 (7) |
C12—C11—C10 | 120.7 (2) | N1—Ni1—O2 | 107.59 (7) |
C13iii—C11—C10 | 120.6 (2) | O1—Ni1—O2 | 61.46 (6) |
C11—C12—C13 | 120.5 (2) | O3—Ni1—C1 | 86.82 (7) |
C11—C12—H12 | 119.8 | O5—Ni1—C1 | 132.01 (7) |
C13—C12—H12 | 119.8 | N3—Ni1—C1 | 86.56 (7) |
C12—C13—C11iii | 120.9 (2) | N1—Ni1—C1 | 138.19 (8) |
C12—C13—H13 | 119.6 | O1—Ni1—C1 | 30.77 (7) |
C11iii—C13—H13 | 119.6 | O2—Ni1—C1 | 30.69 (7) |
C15—C14—H14A | 109.5 | C1—O1—Ni1 | 90.06 (13) |
C15—C14—H14B | 109.5 | C1—O2—Ni1 | 88.47 (13) |
H14A—C14—H14B | 109.5 | C5—O3—Ni1 | 127.51 (15) |
C15—C14—H14C | 109.5 | Ni1—O5—H5A | 97.0 |
H14A—C14—H14C | 109.5 | Ni1—O5—H5B | 116.7 |
H14B—C14—H14C | 109.5 | H5A—O5—H5B | 114.7 |
| | | |
O2—C1—C2—C3i | −56.0 (3) | N1—C7—N2—C10 | −166.5 (2) |
O1—C1—C2—C3i | 123.0 (2) | C6—C7—N2—C10 | 13.2 (4) |
C2ii—C3—C4—C5 | −161.4 (2) | C9—C8—N2—C7 | −0.2 (3) |
C3—C4—C5—O4 | 1.0 (4) | C9—C8—N2—C10 | 166.3 (2) |
C3—C4—C5—O3 | 177.5 (2) | C11—C10—N2—C7 | 68.9 (3) |
N2—C8—C9—N1 | 0.7 (3) | C11—C10—N2—C8 | −94.8 (3) |
N2—C10—C11—C12 | −119.4 (2) | N4—C15—N3—C16 | 0.6 (2) |
N2—C10—C11—C13iii | 58.4 (3) | C14—C15—N3—C16 | −178.8 (2) |
C13iii—C11—C12—C13 | 0.0 (4) | N4—C15—N3—Ni1 | 169.04 (14) |
C10—C11—C12—C13 | 177.9 (2) | C14—C15—N3—Ni1 | −10.3 (3) |
C11—C12—C13—C11iii | 0.0 (4) | C17—C16—N3—C15 | −0.1 (3) |
N3—C16—C17—N4 | −0.4 (3) | C17—C16—N3—Ni1 | −168.90 (16) |
N4—C18—C19—C21 | 165.9 (2) | N3—C15—N4—C17 | −0.8 (3) |
N4—C18—C19—C20 | −14.9 (3) | C14—C15—N4—C17 | 178.6 (2) |
C21—C19—C20—C21iv | 0.0 (4) | N3—C15—N4—C18 | 178.1 (2) |
C18—C19—C20—C21iv | −179.2 (2) | C14—C15—N4—C18 | −2.5 (3) |
C20—C19—C21—C20iv | 0.0 (4) | C16—C17—N4—C15 | 0.7 (3) |
C18—C19—C21—C20iv | 179.2 (2) | C16—C17—N4—C18 | −178.2 (2) |
N2—C7—N1—C9 | 0.8 (3) | C19—C18—N4—C15 | −69.1 (3) |
C6—C7—N1—C9 | −178.9 (2) | C19—C18—N4—C17 | 109.6 (3) |
N2—C7—N1—Ni1 | 165.07 (16) | O2—C1—O1—Ni1 | 0.3 (2) |
C6—C7—N1—Ni1 | −14.6 (4) | C2—C1—O1—Ni1 | −178.66 (18) |
C8—C9—N1—C7 | −0.9 (3) | O1—C1—O2—Ni1 | −0.31 (19) |
C8—C9—N1—Ni1 | −166.32 (17) | C2—C1—O2—Ni1 | 178.67 (18) |
N1—C7—N2—C8 | −0.4 (3) | O4—C5—O3—Ni1 | 12.1 (4) |
C6—C7—N2—C8 | 179.3 (2) | C4—C5—O3—Ni1 | −164.25 (17) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x, −y, −z+1; (iv) −x+1/2, −y−1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O4 | 0.85 | 1.76 | 2.602 (2) | 168 |
O5—H5B···O1v | 0.86 | 1.84 | 2.694 (2) | 175 |
O6—H6D···O2 | 0.85 | 2.00 | 2.837 (2) | 171 |
Symmetry code: (v) −x+1, y, −z+1/2. |
Poly[[{µ
2-1,4-bis[(2-methyl-1
H-imidazol-1-yl)methyl]benzene}(µ
2-glutarato)zinc(II)] tetrahydrate] (2)
top
Crystal data top
[Zn(C5H6O4)(C16H18N4)]·4H2O | F(000) = 1120 |
Mr = 533.87 | Dx = 1.399 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6488 (5) Å | Cell parameters from 9985 reflections |
b = 17.7245 (12) Å | θ = 2.7–26.4° |
c = 14.9109 (10) Å | µ = 1.02 mm−1 |
β = 96.470 (2)° | T = 153 K |
V = 2533.8 (3) Å3 | Block, yellow |
Z = 4 | 0.20 × 0.20 × 0.20 mm |
Data collection top
Bruker SMART CCD area detector diffractometer | Rint = 0.058 |
phi and ω scans | θmax = 26.4°, θmin = 2.3° |
48372 measured reflections | h = −12→10 |
5192 independent reflections | k = −22→22 |
4250 reflections with I > 2σ(I) | l = −18→18 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0356P)2 + 2.5686P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
5192 reflections | Δρmax = 0.42 e Å−3 |
309 parameters | Δρmin = −0.42 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 | |
C1 | 0.4978 (2) | −0.13516 (13) | 0.72047 (14) | 0.0180 (4) | |
C2 | 0.6126 (2) | −0.19220 (13) | 0.71341 (15) | 0.0200 (5) | |
H2A | 0.6006 | −0.2144 | 0.6521 | 0.024* | |
H2B | 0.6022 | −0.2335 | 0.7569 | 0.024* | |
C3 | 0.7595 (2) | −0.16064 (13) | 0.73130 (15) | 0.0196 (5) | |
H3A | 0.7782 | −0.1274 | 0.6807 | 0.024* | |
H3B | 0.7674 | −0.1299 | 0.7871 | 0.024* | |
C4 | −0.1332 (2) | −0.22344 (13) | 0.74156 (15) | 0.0199 (5) | |
H4A | −0.1516 | −0.2551 | 0.7936 | 0.024* | |
H4B | −0.1468 | −0.2556 | 0.6870 | 0.024* | |
C5 | 0.0176 (2) | −0.19864 (13) | 0.75522 (14) | 0.0185 (4) | |
C6 | 0.0311 (2) | 0.06867 (14) | 0.68859 (17) | 0.0273 (5) | |
H6A | 0.0518 | 0.0399 | 0.7446 | 0.041* | |
H6B | −0.0679 | 0.0631 | 0.6663 | 0.041* | |
H6C | 0.0523 | 0.1221 | 0.7002 | 0.041* | |
C7 | 0.1173 (2) | 0.03982 (13) | 0.62001 (15) | 0.0212 (5) | |
C8 | 0.2610 (2) | −0.02752 (14) | 0.55012 (16) | 0.0256 (5) | |
H8 | 0.3276 | −0.0647 | 0.5385 | 0.031* | |
C9 | 0.2063 (3) | 0.02435 (14) | 0.49115 (17) | 0.0295 (6) | |
H9 | 0.2260 | 0.0305 | 0.4306 | 0.035* | |
C10 | 0.0436 (2) | 0.13459 (13) | 0.49878 (17) | 0.0273 (5) | |
H10A | −0.0420 | 0.1421 | 0.5286 | 0.033* | |
H10B | 0.0148 | 0.1267 | 0.4336 | 0.033* | |
C11 | 0.1323 (2) | 0.20514 (13) | 0.51076 (14) | 0.0206 (5) | |
C12 | 0.0695 (2) | 0.27467 (13) | 0.49135 (16) | 0.0245 (5) | |
H12 | −0.0281 | 0.2771 | 0.4738 | 0.029* | |
C13 | 0.1474 (2) | 0.34040 (13) | 0.49732 (16) | 0.0260 (5) | |
H13 | 0.1029 | 0.3875 | 0.4837 | 0.031* | |
C14 | 0.2905 (2) | 0.33805 (13) | 0.52314 (15) | 0.0222 (5) | |
C15 | 0.3532 (2) | 0.26898 (14) | 0.54289 (15) | 0.0236 (5) | |
H15 | 0.4508 | 0.2666 | 0.5605 | 0.028* | |
C16 | 0.2753 (2) | 0.20320 (13) | 0.53736 (16) | 0.0234 (5) | |
H16 | 0.3198 | 0.1563 | 0.5519 | 0.028* | |
C17 | 0.3801 (3) | 0.09166 (14) | 1.03323 (17) | 0.0297 (6) | |
H17A | 0.4741 | 0.1039 | 1.0168 | 0.036* | |
H17B | 0.3906 | 0.0759 | 1.0973 | 0.036* | |
C18 | 0.2518 (3) | −0.03186 (14) | 1.00758 (17) | 0.0310 (6) | |
H18 | 0.2327 | −0.0412 | 1.0677 | 0.037* | |
C19 | 0.2143 (3) | −0.07527 (14) | 0.93433 (17) | 0.0283 (5) | |
H19 | 0.1640 | −0.1213 | 0.9344 | 0.034* | |
C20 | 0.3262 (2) | 0.02117 (12) | 0.88750 (15) | 0.0200 (5) | |
C21 | 0.3902 (3) | 0.07732 (13) | 0.83099 (16) | 0.0265 (5) | |
H21A | 0.3922 | 0.0570 | 0.7700 | 0.040* | |
H21B | 0.4856 | 0.0882 | 0.8577 | 0.040* | |
H21C | 0.3350 | 0.1239 | 0.8279 | 0.040* | |
N1 | 0.20437 (19) | −0.01819 (11) | 0.63150 (13) | 0.0214 (4) | |
N2 | 0.1151 (2) | 0.06730 (11) | 0.53570 (13) | 0.0243 (4) | |
N3 | 0.26085 (19) | −0.04195 (10) | 0.85923 (12) | 0.0202 (4) | |
N4 | 0.3232 (2) | 0.02870 (11) | 0.97759 (13) | 0.0245 (4) | |
O1 | 0.37261 (15) | −0.16221 (9) | 0.70795 (11) | 0.0219 (3) | |
O2 | 0.52141 (16) | −0.06823 (9) | 0.73858 (12) | 0.0278 (4) | |
O3 | 0.04370 (15) | −0.13169 (9) | 0.73117 (12) | 0.0261 (4) | |
O4 | 0.10728 (17) | −0.24431 (10) | 0.78700 (13) | 0.0330 (4) | |
O5 | 0.1837 (2) | 0.63348 (11) | 0.67748 (13) | 0.0428 (5) | |
H5A | 0.2387 | 0.6553 | 0.6459 | 0.064* | |
H5B | 0.1495 | 0.6641 | 0.7129 | 0.064* | |
O6 | 0.3323 (2) | 0.72546 (12) | 0.57719 (14) | 0.0518 (6) | |
H6D | 0.3308 | 0.7425 | 0.5238 | 0.078* | |
H6E | 0.3333 | 0.7629 | 0.6128 | 0.078* | |
O7 | 0.3091 (3) | 0.80210 (14) | 0.41424 (16) | 0.0709 (8) | |
H7A | 0.3352 | 0.8440 | 0.3930 | 0.106* | |
H7B | 0.2572 | 0.7749 | 0.3770 | 0.106* | |
O8 | 0.3387 (2) | 0.94059 (13) | 0.32155 (14) | 0.0556 (6) | |
H8A | 0.3917 | 0.9772 | 0.3103 | 0.083* | |
H8B | 0.3030 | 0.9162 | 0.2747 | 0.083* | |
Zn1 | 0.23267 (2) | −0.08933 (2) | 0.73666 (2) | 0.01675 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0149 (10) | 0.0215 (12) | 0.0176 (10) | 0.0011 (9) | 0.0015 (8) | 0.0010 (9) |
C2 | 0.0138 (10) | 0.0202 (11) | 0.0260 (12) | 0.0015 (9) | 0.0024 (9) | −0.0036 (9) |
C3 | 0.0140 (10) | 0.0197 (11) | 0.0253 (11) | 0.0006 (8) | 0.0032 (9) | 0.0016 (9) |
C4 | 0.0141 (10) | 0.0207 (11) | 0.0252 (11) | 0.0000 (9) | 0.0036 (9) | 0.0021 (9) |
C5 | 0.0163 (10) | 0.0212 (12) | 0.0185 (10) | 0.0022 (9) | 0.0038 (8) | −0.0031 (9) |
C6 | 0.0254 (12) | 0.0267 (13) | 0.0305 (13) | 0.0029 (10) | 0.0064 (10) | −0.0038 (10) |
C7 | 0.0202 (11) | 0.0184 (11) | 0.0242 (11) | −0.0056 (9) | −0.0011 (9) | 0.0014 (9) |
C8 | 0.0274 (12) | 0.0242 (12) | 0.0262 (12) | −0.0015 (10) | 0.0083 (10) | −0.0029 (10) |
C9 | 0.0409 (15) | 0.0238 (13) | 0.0256 (12) | −0.0050 (11) | 0.0115 (11) | −0.0012 (10) |
C10 | 0.0270 (12) | 0.0218 (13) | 0.0310 (13) | −0.0045 (10) | −0.0065 (10) | 0.0062 (10) |
C11 | 0.0242 (11) | 0.0208 (12) | 0.0164 (10) | −0.0029 (9) | 0.0015 (9) | 0.0029 (9) |
C12 | 0.0201 (11) | 0.0250 (12) | 0.0271 (12) | 0.0001 (9) | −0.0028 (9) | 0.0031 (10) |
C13 | 0.0285 (13) | 0.0180 (12) | 0.0303 (13) | 0.0022 (10) | −0.0019 (10) | 0.0046 (10) |
C14 | 0.0266 (12) | 0.0219 (12) | 0.0175 (11) | −0.0050 (9) | 0.0007 (9) | 0.0036 (9) |
C15 | 0.0190 (11) | 0.0269 (13) | 0.0243 (12) | −0.0010 (9) | 0.0007 (9) | 0.0029 (10) |
C16 | 0.0241 (12) | 0.0187 (12) | 0.0267 (12) | 0.0027 (9) | −0.0006 (9) | 0.0029 (9) |
C17 | 0.0338 (13) | 0.0262 (13) | 0.0267 (12) | 0.0102 (11) | −0.0068 (10) | −0.0071 (10) |
C18 | 0.0431 (15) | 0.0265 (13) | 0.0246 (12) | 0.0076 (11) | 0.0095 (11) | 0.0055 (10) |
C19 | 0.0327 (13) | 0.0238 (13) | 0.0297 (13) | −0.0004 (10) | 0.0099 (10) | 0.0046 (10) |
C20 | 0.0202 (11) | 0.0188 (11) | 0.0208 (11) | 0.0055 (9) | 0.0013 (9) | −0.0026 (9) |
C21 | 0.0297 (13) | 0.0211 (12) | 0.0292 (13) | −0.0047 (10) | 0.0049 (10) | −0.0015 (10) |
N1 | 0.0215 (9) | 0.0195 (10) | 0.0237 (10) | −0.0011 (8) | 0.0041 (8) | −0.0001 (8) |
N2 | 0.0263 (10) | 0.0192 (10) | 0.0264 (10) | −0.0045 (8) | −0.0014 (8) | 0.0035 (8) |
N3 | 0.0200 (9) | 0.0185 (10) | 0.0224 (10) | 0.0017 (7) | 0.0031 (7) | −0.0001 (8) |
N4 | 0.0320 (11) | 0.0185 (10) | 0.0224 (10) | 0.0064 (8) | 0.0001 (8) | −0.0024 (8) |
O1 | 0.0121 (7) | 0.0219 (8) | 0.0316 (9) | −0.0009 (6) | 0.0023 (6) | −0.0058 (7) |
O2 | 0.0180 (8) | 0.0207 (9) | 0.0444 (10) | −0.0009 (6) | 0.0026 (7) | −0.0059 (7) |
O3 | 0.0144 (8) | 0.0242 (9) | 0.0394 (10) | −0.0019 (7) | 0.0024 (7) | 0.0031 (7) |
O4 | 0.0180 (8) | 0.0322 (10) | 0.0480 (11) | 0.0065 (7) | −0.0001 (8) | 0.0080 (8) |
O5 | 0.0566 (13) | 0.0346 (11) | 0.0403 (11) | 0.0072 (9) | 0.0188 (10) | 0.0036 (9) |
O6 | 0.0689 (15) | 0.0473 (13) | 0.0419 (12) | −0.0270 (11) | 0.0184 (10) | −0.0191 (10) |
O7 | 0.0906 (19) | 0.0507 (15) | 0.0599 (15) | −0.0202 (13) | −0.0419 (14) | 0.0082 (12) |
O8 | 0.0687 (15) | 0.0553 (14) | 0.0470 (13) | −0.0366 (12) | 0.0251 (11) | −0.0152 (11) |
Zn1 | 0.01253 (12) | 0.01537 (13) | 0.02229 (13) | 0.00008 (10) | 0.00168 (9) | −0.00060 (10) |
Geometric parameters (Å, º) top
C1—O2 | 1.232 (3) | C13—C14 | 1.392 (3) |
C1—O1 | 1.293 (3) | C13—H13 | 0.9500 |
C1—C2 | 1.512 (3) | C14—C15 | 1.382 (3) |
C2—C3 | 1.519 (3) | C14—C17iii | 1.514 (3) |
C2—H2A | 0.9900 | C15—C16 | 1.385 (3) |
C2—H2B | 0.9900 | C15—H15 | 0.9500 |
C3—C4i | 1.516 (3) | C16—H16 | 0.9500 |
C3—H3A | 0.9900 | C17—N4 | 1.460 (3) |
C3—H3B | 0.9900 | C17—C14iv | 1.514 (3) |
C4—C5 | 1.511 (3) | C17—H17A | 0.9900 |
C4—C3ii | 1.516 (3) | C17—H17B | 0.9900 |
C4—H4A | 0.9900 | C18—C19 | 1.352 (4) |
C4—H4B | 0.9900 | C18—N4 | 1.377 (3) |
C5—O4 | 1.240 (3) | C18—H18 | 0.9500 |
C5—O3 | 1.273 (3) | C19—N3 | 1.385 (3) |
C6—C7 | 1.480 (3) | C19—H19 | 0.9500 |
C6—H6A | 0.9800 | C20—N3 | 1.329 (3) |
C6—H6B | 0.9800 | C20—N4 | 1.353 (3) |
C6—H6C | 0.9800 | C20—C21 | 1.483 (3) |
C7—N1 | 1.327 (3) | C21—H21A | 0.9800 |
C7—N2 | 1.346 (3) | C21—H21B | 0.9800 |
C8—C9 | 1.339 (3) | C21—H21C | 0.9800 |
C8—N1 | 1.396 (3) | N1—Zn1 | 2.0065 (19) |
C8—H8 | 0.9500 | N3—Zn1 | 2.0019 (19) |
C9—N2 | 1.388 (3) | O1—Zn1 | 1.9507 (15) |
C9—H9 | 0.9500 | O3—Zn1 | 1.9651 (15) |
C10—N2 | 1.455 (3) | O5—H5A | 0.8415 |
C10—C11 | 1.515 (3) | O5—H5B | 0.8500 |
C10—H10A | 0.9900 | O6—H6D | 0.8501 |
C10—H10B | 0.9900 | O6—H6E | 0.8499 |
C11—C12 | 1.389 (3) | O7—H7A | 0.8556 |
C11—C16 | 1.392 (3) | O7—H7B | 0.8542 |
C12—C13 | 1.384 (3) | O8—H8A | 0.8545 |
C12—H12 | 0.9500 | O8—H8B | 0.8600 |
| | | |
O2—C1—O1 | 122.3 (2) | C15—C14—C13 | 118.8 (2) |
O2—C1—C2 | 122.70 (19) | C15—C14—C17iii | 118.4 (2) |
O1—C1—C2 | 114.94 (19) | C13—C14—C17iii | 122.7 (2) |
C1—C2—C3 | 114.69 (19) | C14—C15—C16 | 120.8 (2) |
C1—C2—H2A | 108.6 | C14—C15—H15 | 119.6 |
C3—C2—H2A | 108.6 | C16—C15—H15 | 119.6 |
C1—C2—H2B | 108.6 | C15—C16—C11 | 120.7 (2) |
C3—C2—H2B | 108.6 | C15—C16—H16 | 119.7 |
H2A—C2—H2B | 107.6 | C11—C16—H16 | 119.7 |
C4i—C3—C2 | 111.12 (18) | N4—C17—C14iv | 113.47 (19) |
C4i—C3—H3A | 109.4 | N4—C17—H17A | 108.9 |
C2—C3—H3A | 109.4 | C14iv—C17—H17A | 108.9 |
C4i—C3—H3B | 109.4 | N4—C17—H17B | 108.9 |
C2—C3—H3B | 109.4 | C14iv—C17—H17B | 108.9 |
H3A—C3—H3B | 108.0 | H17A—C17—H17B | 107.7 |
C5—C4—C3ii | 115.87 (18) | C19—C18—N4 | 106.2 (2) |
C5—C4—H4A | 108.3 | C19—C18—H18 | 126.9 |
C3ii—C4—H4A | 108.3 | N4—C18—H18 | 126.9 |
C5—C4—H4B | 108.3 | C18—C19—N3 | 109.2 (2) |
C3ii—C4—H4B | 108.3 | C18—C19—H19 | 125.4 |
H4A—C4—H4B | 107.4 | N3—C19—H19 | 125.4 |
O4—C5—O3 | 124.4 (2) | N3—C20—N4 | 109.6 (2) |
O4—C5—C4 | 118.8 (2) | N3—C20—C21 | 126.7 (2) |
O3—C5—C4 | 116.82 (19) | N4—C20—C21 | 123.7 (2) |
C7—C6—H6A | 109.5 | C20—C21—H21A | 109.5 |
C7—C6—H6B | 109.5 | C20—C21—H21B | 109.5 |
H6A—C6—H6B | 109.5 | H21A—C21—H21B | 109.5 |
C7—C6—H6C | 109.5 | C20—C21—H21C | 109.5 |
H6A—C6—H6C | 109.5 | H21A—C21—H21C | 109.5 |
H6B—C6—H6C | 109.5 | H21B—C21—H21C | 109.5 |
N1—C7—N2 | 110.1 (2) | C7—N1—C8 | 106.48 (19) |
N1—C7—C6 | 125.1 (2) | C7—N1—Zn1 | 128.06 (16) |
N2—C7—C6 | 124.7 (2) | C8—N1—Zn1 | 124.95 (16) |
C9—C8—N1 | 109.0 (2) | C7—N2—C9 | 107.7 (2) |
C9—C8—H8 | 125.5 | C7—N2—C10 | 127.4 (2) |
N1—C8—H8 | 125.5 | C9—N2—C10 | 124.6 (2) |
C8—C9—N2 | 106.7 (2) | C20—N3—C19 | 106.74 (19) |
C8—C9—H9 | 126.7 | C20—N3—Zn1 | 130.79 (15) |
N2—C9—H9 | 126.7 | C19—N3—Zn1 | 122.43 (16) |
N2—C10—C11 | 113.24 (19) | C20—N4—C18 | 108.2 (2) |
N2—C10—H10A | 108.9 | C20—N4—C17 | 126.2 (2) |
C11—C10—H10A | 108.9 | C18—N4—C17 | 125.5 (2) |
N2—C10—H10B | 108.9 | C1—O1—Zn1 | 112.41 (14) |
C11—C10—H10B | 108.9 | C5—O3—Zn1 | 123.83 (14) |
H10A—C10—H10B | 107.7 | H5A—O5—H5B | 111.6 |
C12—C11—C16 | 118.4 (2) | H6D—O6—H6E | 107.7 |
C12—C11—C10 | 118.7 (2) | H7A—O7—H7B | 115.0 |
C16—C11—C10 | 122.8 (2) | H8A—O8—H8B | 114.6 |
C13—C12—C11 | 120.8 (2) | O1—Zn1—O3 | 113.56 (7) |
C13—C12—H12 | 119.6 | O1—Zn1—N3 | 116.87 (7) |
C11—C12—H12 | 119.6 | O3—Zn1—N3 | 103.19 (7) |
C12—C13—C14 | 120.5 (2) | O1—Zn1—N1 | 106.34 (7) |
C12—C13—H13 | 119.8 | O3—Zn1—N1 | 99.42 (7) |
C14—C13—H13 | 119.8 | N3—Zn1—N1 | 116.25 (8) |
| | | |
O2—C1—C2—C3 | 0.6 (3) | C6—C7—N2—C9 | −178.1 (2) |
O1—C1—C2—C3 | −178.03 (18) | N1—C7—N2—C10 | −173.9 (2) |
C1—C2—C3—C4i | 168.53 (19) | C6—C7—N2—C10 | 8.1 (4) |
C3ii—C4—C5—O4 | 161.4 (2) | C8—C9—N2—C7 | −0.2 (3) |
C3ii—C4—C5—O3 | −19.9 (3) | C8—C9—N2—C10 | 173.7 (2) |
N1—C8—C9—N2 | 0.5 (3) | C11—C10—N2—C7 | 90.0 (3) |
N2—C10—C11—C12 | −170.0 (2) | C11—C10—N2—C9 | −82.8 (3) |
N2—C10—C11—C16 | 12.3 (3) | N4—C20—N3—C19 | 0.3 (2) |
C16—C11—C12—C13 | 0.7 (3) | C21—C20—N3—C19 | −178.0 (2) |
C10—C11—C12—C13 | −177.1 (2) | N4—C20—N3—Zn1 | −177.43 (15) |
C11—C12—C13—C14 | −0.1 (4) | C21—C20—N3—Zn1 | 4.3 (3) |
C12—C13—C14—C15 | −0.2 (4) | C18—C19—N3—C20 | 0.1 (3) |
C12—C13—C14—C17iii | −178.3 (2) | C18—C19—N3—Zn1 | 178.07 (16) |
C13—C14—C15—C16 | −0.1 (3) | N3—C20—N4—C18 | −0.6 (3) |
C17iii—C14—C15—C16 | 178.1 (2) | C21—C20—N4—C18 | 177.8 (2) |
C14—C15—C16—C11 | 0.7 (4) | N3—C20—N4—C17 | −178.1 (2) |
C12—C11—C16—C15 | −1.0 (3) | C21—C20—N4—C17 | 0.3 (4) |
C10—C11—C16—C15 | 176.6 (2) | C19—C18—N4—C20 | 0.6 (3) |
N4—C18—C19—N3 | −0.4 (3) | C19—C18—N4—C17 | 178.1 (2) |
N2—C7—N1—C8 | 0.4 (2) | C14iv—C17—N4—C20 | 76.2 (3) |
C6—C7—N1—C8 | 178.4 (2) | C14iv—C17—N4—C18 | −100.9 (3) |
N2—C7—N1—Zn1 | −171.59 (15) | O2—C1—O1—Zn1 | −7.6 (3) |
C6—C7—N1—Zn1 | 6.4 (3) | C2—C1—O1—Zn1 | 170.97 (14) |
C9—C8—N1—C7 | −0.6 (3) | O4—C5—O3—Zn1 | 1.9 (3) |
C9—C8—N1—Zn1 | 171.76 (16) | C4—C5—O3—Zn1 | −176.64 (14) |
N1—C7—N2—C9 | −0.1 (3) | | |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, −y+1/2, z−1/2; (iv) x, −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—H5A···O6 | 0.84 | 1.90 | 2.727 (3) | 166 |
O5—H5B···O4v | 0.85 | 2.03 | 2.859 (3) | 165 |
O6—H6D···O7 | 0.85 | 1.94 | 2.771 (3) | 167 |
O6—H6E···O1v | 0.85 | 1.95 | 2.783 (2) | 167 |
O7—H7A···O8 | 0.86 | 2.02 | 2.847 (3) | 163 |
O7—H7B···O4iii | 0.85 | 1.94 | 2.758 (3) | 161 |
O8—H8A···O2vi | 0.85 | 1.99 | 2.831 (3) | 167 |
O8—H8B···O5vii | 0.86 | 1.96 | 2.802 (3) | 168 |
Symmetry codes: (iii) x, −y+1/2, z−1/2; (v) x, y+1, z; (vi) −x+1, −y+1, −z+1; (vii) x, −y+3/2, z−1/2. |
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