Two new isostructural complexes, namely, poly[aqua[μ
3-2-(4-carboxyphenoxy)terephthalato-κ
3O1:
O4:
O4′](1,10-phenanthroline-κ
2N,
N′)cobalt(II)], [Co(C
15H
8O
7)(C
12H
8N
2)(H
2O)]
n or [Co(μ
3-Hcpota)(phen)(H
2O)]
n,
I, and poly[aqua[μ
3-2-(4-carboxyphenoxy)terephthalato-κ
3O1:
O4:
O4′](1,10-phenanthroline-κ
2N,
N′)nickel(II)], [Ni(C
15H
8O
7)(C
12H
8N
2)(H
2O)]
n or [Ni(μ
3-Hcpota)(phen)(H
2O)]
n,
II, have been synthesized by solvothermal reactions. Complexes
I and
II were fully characterized by IR spectroscopy, elemental analyses, thermogravimetric analyses, and powder and single-crystal X-ray diffraction. They both present two-dimensional structures based on [
M2(μ-COO)
2]
2+ (
M = Co
II or Ni
II) dinuclear metal units with a
fes topology and a vertex symbol (4·8
2). Interestingly, the positions of the two dimeric metal motifs and the two partially deprotonated Hcpota
2− ligands reproduce regular flying butterfly arrangements flipped upside down and sharing wings in the
ab plane. Magnetic studies indicate antiferromagnetic interactions (
J = −5.21 cm
−1 for
I and −11.53 cm
−1 for
II) in the dimeric units, with Co
Co and Ni
Ni distances of 4.397 (1) and 4.358 (1) Å, respectively, that are related to double
syn–
anti carboxylate bridges.
Supporting information
CCDC references: 2126722; 2126721
For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS2014 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: pubCIF (Westrip, 2010) and PLATON (Spek, 2020).
Poly[aqua[µ
3-2-(4-carboxyphenoxy)terephthalato-
κ3O1:
O4:
O4'](1,10-phenanthroline-
κ2N,
N')cobalt(II)] (I)
top
Crystal data top
[Co(C15H8O7)(C12H8N2)(H2O)] | F(000) = 1140 |
Mr = 557.36 | Dx = 1.496 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6652 (7) Å | Cell parameters from 7425 reflections |
b = 20.9692 (15) Å | θ = 2.7–25.6° |
c = 11.0438 (8) Å | µ = 0.75 mm−1 |
β = 113.609 (2)° | T = 296 K |
V = 2475.3 (3) Å3 | Block, purple |
Z = 4 | 0.15 × 0.15 × 0.12 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2958 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.120 |
φ and ω scans | θmax = 27.2°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −14→14 |
Tmin = 0.684, Tmax = 0.746 | k = −26→26 |
31107 measured reflections | l = −14→14 |
5470 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.072 | H-atom parameters constrained |
wR(F2) = 0.180 | w = 1/[σ2(Fo2) + (0.080P)2 + 2.P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5470 reflections | Δρmax = 0.99 e Å−3 |
343 parameters | Δρmin = −0.46 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 | |
Co1 | 0.58474 (5) | −0.04305 (3) | 0.87391 (6) | 0.0225 (2) | |
O1 | 0.6332 (3) | 0.04886 (14) | 0.9584 (3) | 0.0285 (8) | |
O2 | 0.4570 (3) | 0.07970 (14) | 0.9763 (3) | 0.0283 (8) | |
O3 | 0.6761 (3) | 0.37019 (15) | 0.7748 (4) | 0.0433 (10) | |
O4 | 0.4735 (3) | 0.37383 (14) | 0.7350 (3) | 0.0327 (8) | |
O5 | −0.0999 (4) | 0.3229 (2) | 0.8167 (6) | 0.0809 (16) | |
H5A | −0.1691 | 0.3298 | 0.8166 | 0.121* | |
O6 | −0.0355 (5) | 0.3738 (4) | 1.0053 (8) | 0.159 (3) | |
O7 | 0.4808 (3) | 0.31854 (14) | 0.9703 (3) | 0.0308 (8) | |
O8 | 0.3967 (3) | −0.00741 (15) | 0.7687 (3) | 0.0341 (8) | |
H8A | 0.3953 | 0.0134 | 0.8310 | 0.051* | |
H8B | 0.3472 | −0.0373 | 0.7466 | 0.051* | |
N1 | 0.7697 (3) | −0.07968 (19) | 0.9653 (4) | 0.0335 (10) | |
N2 | 0.6651 (4) | −0.01056 (19) | 0.7450 (4) | 0.0308 (10) | |
C1 | 0.5548 (4) | 0.0901 (2) | 0.9568 (4) | 0.0244 (11) | |
C2 | 0.5714 (4) | 0.1575 (2) | 0.9201 (4) | 0.0202 (10) | |
C3 | 0.5143 (4) | 0.2069 (2) | 0.9576 (4) | 0.0235 (11) | |
H3 | 0.4700 | 0.1988 | 1.0097 | 0.028* | |
C4 | 0.5231 (4) | 0.2683 (2) | 0.9177 (5) | 0.0238 (11) | |
C5 | 0.6387 (4) | 0.1708 (2) | 0.8436 (5) | 0.0272 (11) | |
H5 | 0.6801 | 0.1381 | 0.8208 | 0.033* | |
C6 | 0.6440 (4) | 0.2322 (2) | 0.8015 (5) | 0.0260 (11) | |
H6 | 0.6883 | 0.2406 | 0.7496 | 0.031* | |
C7 | 0.5839 (4) | 0.2817 (2) | 0.8359 (5) | 0.0234 (11) | |
C8 | 0.5794 (4) | 0.3472 (2) | 0.7789 (5) | 0.0262 (11) | |
C9 | 0.3566 (4) | 0.3200 (2) | 0.9518 (5) | 0.0317 (12) | |
C10 | 0.2614 (5) | 0.2978 (3) | 0.8402 (6) | 0.0454 (15) | |
H10 | 0.2771 | 0.2787 | 0.7725 | 0.054* | |
C11 | 0.1387 (5) | 0.3052 (3) | 0.8320 (7) | 0.0550 (17) | |
H11 | 0.0717 | 0.2905 | 0.7579 | 0.066* | |
C12 | 0.1166 (6) | 0.3340 (3) | 0.9321 (7) | 0.0583 (18) | |
C13 | 0.3331 (6) | 0.3483 (3) | 1.0517 (7) | 0.0639 (19) | |
H13 | 0.3993 | 0.3628 | 1.1269 | 0.077* | |
C14 | 0.2125 (7) | 0.3552 (4) | 1.0410 (8) | 0.085 (2) | |
H14 | 0.1969 | 0.3744 | 1.1087 | 0.102* | |
C15 | −0.0159 (8) | 0.3447 (4) | 0.9226 (9) | 0.082 (2) | |
C16 | 0.8179 (5) | −0.1160 (3) | 1.0714 (6) | 0.0517 (16) | |
H16 | 0.7671 | −0.1276 | 1.1147 | 0.062* | |
C17 | 0.9412 (6) | −0.1379 (3) | 1.1219 (8) | 0.079 (2) | |
H17 | 0.9722 | −0.1630 | 1.1976 | 0.094* | |
C18 | 1.0151 (6) | −0.1214 (4) | 1.0572 (9) | 0.081 (3) | |
H18 | 1.0972 | −0.1359 | 1.0884 | 0.097* | |
C19 | 0.9678 (5) | −0.0826 (3) | 0.9434 (7) | 0.0540 (17) | |
C20 | 0.8437 (4) | −0.0637 (2) | 0.9009 (6) | 0.0348 (13) | |
C21 | 0.7881 (5) | −0.0261 (2) | 0.7845 (5) | 0.0361 (13) | |
C22 | 0.8600 (6) | −0.0062 (3) | 0.7166 (7) | 0.0603 (19) | |
C23 | 0.9875 (7) | −0.0248 (4) | 0.7637 (9) | 0.081 (3) | |
H23 | 1.0355 | −0.0116 | 0.7183 | 0.097* | |
C24 | 1.0401 (6) | −0.0609 (4) | 0.8720 (10) | 0.082 (3) | |
H24 | 1.1241 | −0.0721 | 0.9014 | 0.099* | |
C25 | 0.8005 (9) | 0.0319 (4) | 0.6050 (9) | 0.082 (3) | |
H25 | 0.8445 | 0.0462 | 0.5562 | 0.098* | |
C26 | 0.6786 (8) | 0.0480 (3) | 0.5680 (7) | 0.073 (2) | |
H26 | 0.6389 | 0.0738 | 0.4945 | 0.088* | |
C27 | 0.6137 (6) | 0.0258 (3) | 0.6402 (6) | 0.0468 (15) | |
H27 | 0.5300 | 0.0372 | 0.6135 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0221 (3) | 0.0168 (3) | 0.0305 (4) | −0.0015 (3) | 0.0125 (3) | −0.0023 (3) |
O1 | 0.0278 (17) | 0.0160 (17) | 0.040 (2) | 0.0014 (14) | 0.0123 (16) | −0.0009 (15) |
O2 | 0.0341 (18) | 0.0167 (17) | 0.041 (2) | −0.0038 (14) | 0.0217 (16) | 0.0013 (15) |
O3 | 0.0249 (18) | 0.030 (2) | 0.081 (3) | 0.0031 (15) | 0.0275 (19) | 0.0215 (19) |
O4 | 0.0262 (18) | 0.0272 (19) | 0.045 (2) | 0.0074 (15) | 0.0151 (16) | 0.0162 (17) |
O5 | 0.042 (3) | 0.079 (4) | 0.116 (5) | 0.002 (2) | 0.025 (3) | 0.027 (3) |
O6 | 0.075 (4) | 0.259 (9) | 0.162 (7) | 0.035 (5) | 0.068 (4) | −0.066 (6) |
O7 | 0.0319 (18) | 0.0205 (17) | 0.048 (2) | 0.0038 (14) | 0.0240 (17) | 0.0005 (16) |
O8 | 0.0323 (18) | 0.0279 (19) | 0.037 (2) | −0.0016 (15) | 0.0081 (16) | −0.0111 (16) |
N1 | 0.029 (2) | 0.026 (2) | 0.043 (3) | −0.0015 (19) | 0.012 (2) | −0.001 (2) |
N2 | 0.037 (2) | 0.026 (2) | 0.034 (3) | −0.0073 (19) | 0.019 (2) | −0.005 (2) |
C1 | 0.031 (3) | 0.019 (3) | 0.024 (3) | −0.005 (2) | 0.011 (2) | −0.001 (2) |
C2 | 0.019 (2) | 0.016 (2) | 0.024 (3) | −0.0003 (19) | 0.007 (2) | 0.001 (2) |
C3 | 0.027 (2) | 0.021 (3) | 0.029 (3) | −0.002 (2) | 0.017 (2) | 0.000 (2) |
C4 | 0.022 (2) | 0.017 (2) | 0.034 (3) | 0.005 (2) | 0.013 (2) | 0.001 (2) |
C5 | 0.022 (2) | 0.022 (3) | 0.041 (3) | 0.006 (2) | 0.017 (2) | 0.002 (2) |
C6 | 0.023 (2) | 0.027 (3) | 0.032 (3) | 0.000 (2) | 0.015 (2) | 0.005 (2) |
C7 | 0.020 (2) | 0.020 (2) | 0.031 (3) | 0.0014 (19) | 0.011 (2) | 0.006 (2) |
C8 | 0.027 (3) | 0.021 (3) | 0.032 (3) | 0.003 (2) | 0.013 (2) | 0.004 (2) |
C9 | 0.036 (3) | 0.022 (3) | 0.046 (3) | 0.011 (2) | 0.026 (3) | 0.011 (3) |
C10 | 0.036 (3) | 0.046 (4) | 0.055 (4) | 0.006 (3) | 0.018 (3) | 0.001 (3) |
C11 | 0.042 (3) | 0.043 (4) | 0.069 (5) | 0.005 (3) | 0.012 (3) | 0.009 (3) |
C12 | 0.044 (4) | 0.063 (4) | 0.081 (5) | 0.021 (3) | 0.038 (4) | 0.007 (4) |
C13 | 0.051 (4) | 0.080 (5) | 0.074 (5) | 0.011 (3) | 0.039 (4) | −0.015 (4) |
C14 | 0.058 (5) | 0.126 (7) | 0.083 (6) | 0.018 (5) | 0.041 (4) | −0.013 (5) |
C15 | 0.078 (6) | 0.092 (6) | 0.088 (7) | 0.023 (5) | 0.047 (5) | 0.009 (5) |
C16 | 0.040 (3) | 0.043 (4) | 0.061 (4) | 0.006 (3) | 0.008 (3) | 0.009 (3) |
C17 | 0.052 (4) | 0.057 (5) | 0.094 (6) | 0.013 (4) | −0.006 (4) | 0.017 (4) |
C18 | 0.027 (4) | 0.074 (5) | 0.121 (7) | 0.008 (3) | 0.008 (4) | −0.026 (5) |
C19 | 0.029 (3) | 0.051 (4) | 0.074 (5) | −0.001 (3) | 0.012 (3) | −0.030 (4) |
C20 | 0.025 (3) | 0.034 (3) | 0.046 (4) | −0.006 (2) | 0.015 (3) | −0.016 (3) |
C21 | 0.037 (3) | 0.035 (3) | 0.045 (4) | −0.019 (2) | 0.026 (3) | −0.019 (3) |
C22 | 0.068 (5) | 0.061 (4) | 0.075 (5) | −0.033 (4) | 0.053 (4) | −0.031 (4) |
C23 | 0.068 (5) | 0.103 (7) | 0.104 (7) | −0.039 (5) | 0.068 (5) | −0.049 (5) |
C24 | 0.032 (4) | 0.094 (6) | 0.136 (8) | −0.019 (4) | 0.050 (5) | −0.059 (6) |
C25 | 0.121 (7) | 0.080 (6) | 0.087 (6) | −0.047 (5) | 0.086 (6) | −0.022 (5) |
C26 | 0.122 (7) | 0.058 (5) | 0.056 (5) | −0.015 (5) | 0.053 (5) | 0.009 (4) |
C27 | 0.065 (4) | 0.041 (3) | 0.040 (4) | −0.001 (3) | 0.027 (3) | 0.001 (3) |
Geometric parameters (Å, º) top
Co1—O2i | 2.052 (3) | C7—C8 | 1.502 (6) |
Co1—O4ii | 2.072 (3) | C9—C10 | 1.368 (7) |
Co1—N2 | 2.106 (4) | C9—C13 | 1.373 (7) |
Co1—O1 | 2.117 (3) | C10—C11 | 1.406 (7) |
Co1—N1 | 2.126 (4) | C10—H10 | 0.9300 |
Co1—O8 | 2.163 (3) | C11—C12 | 1.371 (9) |
O1—C1 | 1.254 (5) | C11—H11 | 0.9300 |
O2—C1 | 1.263 (5) | C12—C14 | 1.347 (9) |
O2—Co1i | 2.052 (3) | C12—C15 | 1.524 (9) |
O3—C8 | 1.245 (5) | C13—C14 | 1.372 (8) |
O4—C8 | 1.263 (5) | C13—H13 | 0.9300 |
O4—Co1iii | 2.072 (3) | C14—H14 | 0.9300 |
O5—C15 | 1.272 (9) | C16—C17 | 1.395 (8) |
O5—H5A | 0.8200 | C16—H16 | 0.9300 |
O6—C15 | 1.194 (9) | C17—C18 | 1.367 (10) |
O7—C9 | 1.380 (5) | C17—H17 | 0.9300 |
O7—C4 | 1.386 (5) | C18—C19 | 1.410 (10) |
O8—H8A | 0.8200 | C18—H18 | 0.9300 |
O8—H8B | 0.8199 | C19—C20 | 1.388 (7) |
N1—C16 | 1.320 (7) | C19—C24 | 1.440 (10) |
N1—C20 | 1.363 (6) | C20—C21 | 1.423 (8) |
N2—C27 | 1.314 (7) | C21—C22 | 1.394 (8) |
N2—C21 | 1.362 (6) | C22—C25 | 1.398 (10) |
C1—C2 | 1.504 (6) | C22—C23 | 1.420 (10) |
C2—C3 | 1.383 (6) | C23—C24 | 1.340 (11) |
C2—C5 | 1.392 (6) | C23—H23 | 0.9300 |
C3—C4 | 1.377 (6) | C24—H24 | 0.9300 |
C3—H3 | 0.9300 | C25—C26 | 1.356 (10) |
C4—C7 | 1.382 (6) | C25—H25 | 0.9300 |
C5—C6 | 1.379 (6) | C26—C27 | 1.382 (8) |
C5—H5 | 0.9300 | C26—H26 | 0.9300 |
C6—C7 | 1.388 (6) | C27—H27 | 0.9300 |
C6—H6 | 0.9300 | | |
| | | |
O2i—Co1—O4ii | 91.40 (13) | C13—C9—O7 | 115.2 (5) |
O2i—Co1—N2 | 168.36 (14) | C9—C10—C11 | 117.3 (5) |
O4ii—Co1—N2 | 90.62 (14) | C9—C10—H10 | 121.4 |
O2i—Co1—O1 | 95.35 (13) | C11—C10—H10 | 121.4 |
O4ii—Co1—O1 | 171.66 (13) | C12—C11—C10 | 120.8 (6) |
N2—Co1—O1 | 83.75 (14) | C12—C11—H11 | 119.6 |
O2i—Co1—N1 | 90.28 (14) | C10—C11—H11 | 119.6 |
O4ii—Co1—N1 | 90.34 (14) | C14—C12—C11 | 120.5 (6) |
N2—Co1—N1 | 78.24 (16) | C14—C12—C15 | 118.0 (7) |
O1—Co1—N1 | 94.51 (14) | C11—C12—C15 | 121.4 (7) |
O2i—Co1—O8 | 92.61 (12) | C14—C13—C9 | 120.3 (7) |
O4ii—Co1—O8 | 87.30 (12) | C14—C13—H13 | 119.9 |
N2—Co1—O8 | 98.94 (14) | C9—C13—H13 | 119.9 |
O1—Co1—O8 | 87.51 (12) | C12—C14—C13 | 119.9 (7) |
N1—Co1—O8 | 176.31 (15) | C12—C14—H14 | 120.1 |
C1—O1—Co1 | 123.9 (3) | C13—C14—H14 | 120.1 |
C1—O2—Co1i | 136.5 (3) | O6—C15—O5 | 125.0 (8) |
C8—O4—Co1iii | 129.7 (3) | O6—C15—C12 | 121.5 (9) |
C15—O5—H5A | 109.5 | O5—C15—C12 | 113.4 (7) |
C9—O7—C4 | 118.9 (4) | N1—C16—C17 | 123.2 (6) |
Co1—O8—H8A | 95.1 | N1—C16—H16 | 118.4 |
Co1—O8—H8B | 109.7 | C17—C16—H16 | 118.4 |
H8A—O8—H8B | 114.1 | C18—C17—C16 | 118.3 (7) |
C16—N1—C20 | 118.2 (5) | C18—C17—H17 | 120.9 |
C16—N1—Co1 | 128.3 (4) | C16—C17—H17 | 120.9 |
C20—N1—Co1 | 113.4 (3) | C17—C18—C19 | 120.5 (6) |
C27—N2—C21 | 118.2 (5) | C17—C18—H18 | 119.7 |
C27—N2—Co1 | 127.9 (4) | C19—C18—H18 | 119.7 |
C21—N2—Co1 | 113.8 (3) | C20—C19—C18 | 116.7 (6) |
O1—C1—O2 | 125.6 (4) | C20—C19—C24 | 119.0 (7) |
O1—C1—C2 | 118.7 (4) | C18—C19—C24 | 124.3 (6) |
O2—C1—C2 | 115.5 (4) | N1—C20—C19 | 123.0 (6) |
C3—C2—C5 | 119.3 (4) | N1—C20—C21 | 116.9 (4) |
C3—C2—C1 | 119.6 (4) | C19—C20—C21 | 120.0 (5) |
C5—C2—C1 | 121.0 (4) | N2—C21—C22 | 122.6 (6) |
C4—C3—C2 | 119.8 (4) | N2—C21—C20 | 117.6 (4) |
C4—C3—H3 | 120.1 | C22—C21—C20 | 119.8 (5) |
C2—C3—H3 | 120.1 | C21—C22—C25 | 116.9 (6) |
C3—C4—C7 | 121.6 (4) | C21—C22—C23 | 119.2 (7) |
C3—C4—O7 | 119.4 (4) | C25—C22—C23 | 123.9 (7) |
C7—C4—O7 | 118.7 (4) | C24—C23—C22 | 121.4 (7) |
C6—C5—C2 | 120.2 (4) | C24—C23—H23 | 119.3 |
C6—C5—H5 | 119.9 | C22—C23—H23 | 119.3 |
C2—C5—H5 | 119.9 | C23—C24—C19 | 120.5 (6) |
C5—C6—C7 | 120.7 (4) | C23—C24—H24 | 119.7 |
C5—C6—H6 | 119.7 | C19—C24—H24 | 119.7 |
C7—C6—H6 | 119.7 | C26—C25—C22 | 119.9 (6) |
C4—C7—C6 | 118.3 (4) | C26—C25—H25 | 120.1 |
C4—C7—C8 | 121.3 (4) | C22—C25—H25 | 120.1 |
C6—C7—C8 | 120.3 (4) | C25—C26—C27 | 119.6 (7) |
O3—C8—O4 | 125.2 (4) | C25—C26—H26 | 120.2 |
O3—C8—C7 | 119.3 (4) | C27—C26—H26 | 120.2 |
O4—C8—C7 | 115.5 (4) | N2—C27—C26 | 122.8 (6) |
C10—C9—C13 | 121.3 (5) | N2—C27—H27 | 118.6 |
C10—C9—O7 | 123.5 (5) | C26—C27—H27 | 118.6 |
| | | |
Co1—O1—C1—O2 | 41.4 (6) | C14—C12—C15—O6 | 3.9 (12) |
Co1—O1—C1—C2 | −134.4 (3) | C11—C12—C15—O6 | −174.5 (8) |
Co1i—O2—C1—O1 | 59.4 (7) | C14—C12—C15—O5 | −179.8 (7) |
Co1i—O2—C1—C2 | −124.8 (4) | C11—C12—C15—O5 | 1.8 (10) |
O1—C1—C2—C3 | −159.0 (4) | C20—N1—C16—C17 | 1.1 (8) |
O2—C1—C2—C3 | 24.8 (6) | Co1—N1—C16—C17 | 179.3 (5) |
O1—C1—C2—C5 | 24.0 (6) | N1—C16—C17—C18 | −0.8 (10) |
O2—C1—C2—C5 | −152.2 (4) | C16—C17—C18—C19 | 0.8 (11) |
C5—C2—C3—C4 | 0.8 (7) | C17—C18—C19—C20 | −1.1 (10) |
C1—C2—C3—C4 | −176.2 (4) | C17—C18—C19—C24 | 177.5 (6) |
C2—C3—C4—C7 | 2.7 (7) | C16—N1—C20—C19 | −1.5 (7) |
C2—C3—C4—O7 | −171.1 (4) | Co1—N1—C20—C19 | −179.9 (4) |
C9—O7—C4—C3 | −60.3 (6) | C16—N1—C20—C21 | 178.0 (5) |
C9—O7—C4—C7 | 125.8 (4) | Co1—N1—C20—C21 | −0.4 (5) |
C3—C2—C5—C6 | −2.5 (7) | C18—C19—C20—N1 | 1.5 (8) |
C1—C2—C5—C6 | 174.5 (4) | C24—C19—C20—N1 | −177.3 (5) |
C2—C5—C6—C7 | 0.7 (7) | C18—C19—C20—C21 | −178.0 (5) |
C3—C4—C7—C6 | −4.4 (7) | C24—C19—C20—C21 | 3.2 (8) |
O7—C4—C7—C6 | 169.4 (4) | C27—N2—C21—C22 | −1.5 (7) |
C3—C4—C7—C8 | 172.2 (4) | Co1—N2—C21—C22 | −176.5 (4) |
O7—C4—C7—C8 | −14.0 (6) | C27—N2—C21—C20 | 177.7 (4) |
C5—C6—C7—C4 | 2.7 (7) | Co1—N2—C21—C20 | 2.7 (6) |
C5—C6—C7—C8 | −174.0 (4) | N1—C20—C21—N2 | −1.5 (7) |
Co1iii—O4—C8—O3 | 7.2 (7) | C19—C20—C21—N2 | 178.0 (4) |
Co1iii—O4—C8—C7 | −170.7 (3) | N1—C20—C21—C22 | 177.7 (5) |
C4—C7—C8—O3 | 138.5 (5) | C19—C20—C21—C22 | −2.8 (8) |
C6—C7—C8—O3 | −45.0 (7) | N2—C21—C22—C25 | 0.8 (8) |
C4—C7—C8—O4 | −43.4 (6) | C20—C21—C22—C25 | −178.4 (5) |
C6—C7—C8—O4 | 133.1 (5) | N2—C21—C22—C23 | −179.6 (5) |
C4—O7—C9—C10 | −34.0 (7) | C20—C21—C22—C23 | 1.2 (8) |
C4—O7—C9—C13 | 148.9 (5) | C21—C22—C23—C24 | −0.1 (11) |
C13—C9—C10—C11 | 0.0 (8) | C25—C22—C23—C24 | 179.4 (7) |
O7—C9—C10—C11 | −176.9 (5) | C22—C23—C24—C19 | 0.6 (12) |
C9—C10—C11—C12 | 0.5 (9) | C20—C19—C24—C23 | −2.2 (10) |
C10—C11—C12—C14 | −0.7 (10) | C18—C19—C24—C23 | 179.2 (7) |
C10—C11—C12—C15 | 177.7 (6) | C21—C22—C25—C26 | 0.3 (10) |
C10—C9—C13—C14 | −0.3 (10) | C23—C22—C25—C26 | −179.2 (7) |
O7—C9—C13—C14 | 176.9 (6) | C22—C25—C26—C27 | −0.8 (11) |
C11—C12—C14—C13 | 0.4 (12) | C21—N2—C27—C26 | 0.9 (8) |
C15—C12—C14—C13 | −178.0 (7) | Co1—N2—C27—C26 | 175.2 (4) |
C9—C13—C14—C12 | 0.1 (12) | C25—C26—C27—N2 | 0.2 (10) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O2i | 0.93 | 2.60 | 3.128 (6) | 117 |
O8—H8B···O3ii | 0.82 | 1.96 | 2.686 (4) | 147 |
O8—H8A···O2 | 0.82 | 2.02 | 2.792 (4) | 156 |
O5—H5A···O3iv | 0.82 | 1.88 | 2.656 (5) | 158 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iv) x−1, y, z. |
Poly[aqua[µ
3-2-(4-carboxyphenoxy)terephthalato-
κ3O1:
O4:
O4'](1,10-phenanthroline-
κ2N,
N')nickel(II)] (II)
top
Crystal data top
[Ni(C15H8O7)(C12H8N2)(H2O)] | F(000) = 1144 |
Mr = 557.14 | Dx = 1.514 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6277 (8) Å | Cell parameters from 5514 reflections |
b = 20.8495 (14) Å | θ = 2.7–25.8° |
c = 11.0075 (9) Å | µ = 0.85 mm−1 |
β = 113.689 (2)° | T = 296 K |
V = 2443.7 (3) Å3 | Block, aquamarine |
Z = 4 | 0.20 × 0.20 × 0.15 mm |
Data collection top
Bruker APEXII CCD diffractometer | 3548 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.089 |
φ and ω scans | θmax = 28.3°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −14→15 |
Tmin = 0.685, Tmax = 0.746 | k = −27→26 |
23793 measured reflections | l = −14→14 |
6067 independent reflections | |
Refinement top
Refinement on F2 | 12 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.060P)2 + 3.4853P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
6067 reflections | Δρmax = 0.89 e Å−3 |
352 parameters | Δρmin = −0.45 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 | Occ. (<1) |
Ni1 | 0.08533 (5) | 0.45754 (2) | 0.37523 (5) | 0.01871 (16) | |
C1 | −0.0563 (4) | 0.41018 (18) | 0.5405 (4) | 0.0199 (9) | |
C2 | −0.0731 (4) | 0.34262 (18) | 0.5781 (4) | 0.0205 (9) | |
C3 | −0.0135 (4) | 0.29299 (18) | 0.5421 (4) | 0.0226 (9) | |
H3 | 0.0315 | 0.3013 | 0.4905 | 0.027* | |
C4 | −0.1398 (4) | 0.32910 (19) | 0.6544 (4) | 0.0257 (10) | |
H4 | −0.1823 | 0.3620 | 0.6760 | 0.031* | |
C5 | −0.0212 (3) | 0.23146 (17) | 0.5830 (4) | 0.0190 (8) | |
C6 | −0.0822 (4) | 0.21841 (18) | 0.6659 (4) | 0.0209 (9) | |
C7 | −0.1444 (4) | 0.26792 (18) | 0.6990 (4) | 0.0234 (9) | |
H7 | −0.1890 | 0.2597 | 0.7511 | 0.028* | |
C8 | 0.1452 (4) | 0.1799 (2) | 0.5483 (5) | 0.0318 (11) | |
C9 | 0.1675 (5) | 0.1527 (3) | 0.4461 (6) | 0.0609 (17) | |
H9 | 0.1009 | 0.1385 | 0.3703 | 0.073* | |
C10 | 0.2412 (4) | 0.2015 (2) | 0.6608 (5) | 0.0440 (13) | |
H10 | 0.2256 | 0.2201 | 0.7294 | 0.053* | |
C11 | 0.3648 (5) | 0.1945 (2) | 0.6692 (6) | 0.0507 (14) | |
H11 | 0.4324 | 0.2084 | 0.7444 | 0.061* | |
C12 | 0.2881 (6) | 0.1467 (4) | 0.4566 (7) | 0.077 (2) | |
H12 | 0.3037 | 0.1283 | 0.3877 | 0.093* | |
C13 | 0.3850 (5) | 0.1673 (3) | 0.5670 (7) | 0.0555 (16) | |
C14 | 0.5198 (7) | 0.1553 (3) | 0.5773 (8) | 0.0716 (19) | |
C15 | 0.3141 (5) | 0.3849 (2) | 0.5728 (5) | 0.0430 (13) | |
H15 | 0.2636 | 0.3738 | 0.6170 | 0.052* | |
C16 | 0.4373 (5) | 0.3625 (3) | 0.6225 (7) | 0.0656 (18) | |
H16 | 0.4685 | 0.3369 | 0.6979 | 0.079* | |
C17 | 0.5110 (5) | 0.3790 (3) | 0.5576 (7) | 0.070 (2) | |
H17 | 0.5934 | 0.3644 | 0.5889 | 0.084* | |
C18 | 0.4643 (4) | 0.4177 (3) | 0.4448 (6) | 0.0464 (14) | |
C19 | 0.3395 (4) | 0.4366 (2) | 0.4016 (5) | 0.0324 (11) | |
C20 | 0.5348 (6) | 0.4398 (3) | 0.3713 (8) | 0.073 (2) | |
H20 | 0.6192 | 0.4289 | 0.4007 | 0.087* | |
C21 | 0.4829 (6) | 0.4753 (4) | 0.2629 (8) | 0.072 (2) | |
H21 | 0.5311 | 0.4877 | 0.2171 | 0.087* | |
C22 | 0.2830 (4) | 0.4747 (2) | 0.2844 (5) | 0.0325 (11) | |
C23 | 0.3544 (5) | 0.4948 (3) | 0.2148 (6) | 0.0486 (14) | |
C24 | 0.2949 (7) | 0.5329 (3) | 0.1031 (7) | 0.0681 (19) | |
H24 | 0.3385 | 0.5470 | 0.0535 | 0.082* | |
C25 | 0.1725 (7) | 0.5493 (3) | 0.0674 (6) | 0.0639 (18) | |
H25 | 0.1322 | 0.5752 | −0.0064 | 0.077* | |
C26 | 0.1077 (5) | 0.5273 (2) | 0.1409 (5) | 0.0406 (12) | |
H26 | 0.0239 | 0.5390 | 0.1147 | 0.049* | |
C27 | −0.0750 (4) | 0.15270 (19) | 0.7252 (4) | 0.0226 (9) | |
N1 | 0.2658 (3) | 0.42114 (16) | 0.4663 (4) | 0.0278 (8) | |
N2 | 0.1600 (3) | 0.49065 (16) | 0.2466 (3) | 0.0277 (8) | |
O1 | −0.1361 (2) | 0.45146 (12) | 0.5360 (3) | 0.0241 (6) | |
O2 | 0.0436 (3) | 0.42059 (12) | 0.5242 (3) | 0.0243 (6) | |
O3 | −0.1738 (3) | 0.12863 (14) | 0.7263 (3) | 0.0381 (8) | |
O4 | 0.0307 (2) | 0.12674 (12) | 0.7712 (3) | 0.0270 (7) | |
O5 | 0.0214 (3) | 0.18077 (13) | 0.5319 (3) | 0.0283 (7) | |
O6 | 0.6032 (4) | 0.1765 (2) | 0.6833 (5) | 0.0745 (13) | |
H6 | 0.6616 | 0.1509 | 0.7113 | 0.112* | |
O8 | −0.0965 (2) | 0.49257 (13) | 0.2708 (3) | 0.0280 (7) | |
H8A | −0.1457 | 0.4625 | 0.2444 | 0.042* | |
H8B | −0.1113 | 0.5083 | 0.3321 | 0.042* | |
O7A | 0.5374 (11) | 0.1436 (6) | 0.4753 (13) | 0.087 (4) | 0.5 |
O7B | 0.5349 (11) | 0.1113 (6) | 0.5060 (13) | 0.088 (4) | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0197 (3) | 0.0143 (2) | 0.0243 (3) | −0.0014 (2) | 0.0110 (2) | −0.0015 (2) |
C1 | 0.024 (2) | 0.017 (2) | 0.018 (2) | −0.0026 (18) | 0.0070 (17) | −0.0014 (16) |
C2 | 0.022 (2) | 0.016 (2) | 0.022 (2) | 0.0008 (17) | 0.0073 (18) | 0.0018 (17) |
C3 | 0.025 (2) | 0.019 (2) | 0.029 (2) | −0.0030 (17) | 0.0158 (19) | 0.0009 (18) |
C4 | 0.025 (2) | 0.019 (2) | 0.039 (3) | 0.0039 (18) | 0.018 (2) | −0.0019 (19) |
C5 | 0.019 (2) | 0.0152 (19) | 0.024 (2) | 0.0023 (16) | 0.0095 (17) | −0.0008 (17) |
C6 | 0.020 (2) | 0.020 (2) | 0.023 (2) | −0.0004 (17) | 0.0088 (18) | 0.0047 (17) |
C7 | 0.025 (2) | 0.021 (2) | 0.032 (2) | 0.0022 (18) | 0.0190 (19) | 0.0050 (18) |
C8 | 0.032 (3) | 0.022 (2) | 0.050 (3) | 0.010 (2) | 0.026 (2) | 0.009 (2) |
C9 | 0.044 (3) | 0.082 (4) | 0.069 (4) | 0.012 (3) | 0.035 (3) | −0.009 (3) |
C10 | 0.035 (3) | 0.042 (3) | 0.055 (4) | 0.007 (2) | 0.019 (3) | 0.002 (3) |
C11 | 0.040 (3) | 0.043 (3) | 0.063 (4) | 0.002 (3) | 0.014 (3) | 0.008 (3) |
C12 | 0.056 (4) | 0.112 (6) | 0.074 (5) | 0.016 (4) | 0.036 (4) | −0.016 (4) |
C13 | 0.044 (3) | 0.061 (4) | 0.076 (4) | 0.020 (3) | 0.040 (3) | 0.008 (3) |
C14 | 0.077 (5) | 0.076 (5) | 0.072 (5) | 0.012 (4) | 0.040 (4) | −0.002 (4) |
C15 | 0.035 (3) | 0.039 (3) | 0.050 (3) | 0.004 (2) | 0.012 (3) | 0.007 (3) |
C16 | 0.043 (4) | 0.062 (4) | 0.071 (4) | 0.012 (3) | 0.000 (3) | 0.014 (3) |
C17 | 0.028 (3) | 0.064 (4) | 0.097 (5) | 0.014 (3) | 0.003 (3) | −0.018 (4) |
C18 | 0.022 (3) | 0.051 (3) | 0.065 (4) | −0.005 (2) | 0.016 (3) | −0.027 (3) |
C19 | 0.025 (2) | 0.030 (2) | 0.044 (3) | −0.005 (2) | 0.015 (2) | −0.018 (2) |
C20 | 0.037 (3) | 0.082 (5) | 0.113 (6) | −0.018 (3) | 0.045 (4) | −0.054 (5) |
C21 | 0.055 (4) | 0.092 (5) | 0.097 (5) | −0.032 (4) | 0.059 (4) | −0.042 (4) |
C22 | 0.037 (3) | 0.029 (2) | 0.042 (3) | −0.015 (2) | 0.027 (2) | −0.017 (2) |
C23 | 0.057 (4) | 0.049 (3) | 0.061 (4) | −0.028 (3) | 0.047 (3) | −0.025 (3) |
C24 | 0.102 (5) | 0.069 (4) | 0.067 (4) | −0.034 (4) | 0.069 (4) | −0.014 (4) |
C25 | 0.104 (6) | 0.055 (4) | 0.047 (4) | −0.015 (4) | 0.044 (4) | 0.007 (3) |
C26 | 0.058 (3) | 0.035 (3) | 0.030 (3) | −0.002 (2) | 0.019 (2) | −0.002 (2) |
C27 | 0.026 (2) | 0.018 (2) | 0.026 (2) | 0.0018 (18) | 0.0126 (19) | 0.0048 (17) |
N1 | 0.0223 (19) | 0.0240 (19) | 0.034 (2) | −0.0023 (16) | 0.0084 (17) | −0.0045 (17) |
N2 | 0.031 (2) | 0.0244 (19) | 0.031 (2) | −0.0041 (16) | 0.0164 (17) | −0.0047 (16) |
O1 | 0.0243 (15) | 0.0139 (14) | 0.0342 (17) | 0.0005 (12) | 0.0117 (13) | −0.0006 (12) |
O2 | 0.0273 (16) | 0.0159 (14) | 0.0354 (17) | −0.0024 (12) | 0.0185 (14) | 0.0029 (12) |
O3 | 0.0226 (16) | 0.0257 (16) | 0.070 (2) | 0.0031 (13) | 0.0231 (16) | 0.0188 (16) |
O4 | 0.0208 (15) | 0.0218 (15) | 0.0396 (18) | 0.0041 (13) | 0.0133 (14) | 0.0142 (13) |
O5 | 0.0313 (17) | 0.0191 (15) | 0.0423 (19) | 0.0019 (13) | 0.0227 (15) | −0.0010 (13) |
O6 | 0.038 (2) | 0.072 (3) | 0.107 (4) | 0.005 (2) | 0.022 (2) | 0.020 (3) |
O8 | 0.0265 (16) | 0.0228 (15) | 0.0310 (17) | −0.0017 (13) | 0.0079 (13) | −0.0069 (13) |
O7A | 0.081 (5) | 0.102 (6) | 0.095 (5) | 0.011 (4) | 0.052 (4) | −0.003 (4) |
O7B | 0.078 (5) | 0.098 (6) | 0.100 (6) | 0.018 (4) | 0.049 (4) | −0.010 (4) |
Geometric parameters (Å, º) top
Ni1—O2 | 2.039 (3) | C14—O7B | 1.266 (13) |
Ni1—O4i | 2.054 (3) | C15—N1 | 1.316 (6) |
Ni1—N2 | 2.055 (3) | C15—C16 | 1.394 (7) |
Ni1—N1 | 2.072 (3) | C15—H15 | 0.9300 |
Ni1—O8 | 2.091 (3) | C16—C17 | 1.361 (9) |
Ni1—O1ii | 2.107 (3) | C16—H16 | 0.9300 |
C1—O1 | 1.252 (5) | C17—C18 | 1.395 (8) |
C1—O2 | 1.263 (4) | C17—H17 | 0.9300 |
C1—C2 | 1.503 (5) | C18—C19 | 1.391 (6) |
C2—C4 | 1.383 (6) | C18—C20 | 1.439 (8) |
C2—C3 | 1.389 (5) | C19—N1 | 1.355 (6) |
C3—C5 | 1.375 (5) | C19—C22 | 1.430 (7) |
C3—H3 | 0.9300 | C20—C21 | 1.325 (9) |
C4—C7 | 1.376 (5) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C21—C23 | 1.430 (9) |
C5—O5 | 1.380 (4) | C21—H21 | 0.9300 |
C5—C6 | 1.390 (5) | C22—N2 | 1.360 (6) |
C6—C7 | 1.390 (5) | C22—C23 | 1.401 (6) |
C6—C27 | 1.505 (5) | C23—C24 | 1.392 (8) |
C7—H7 | 0.9300 | C24—C25 | 1.359 (9) |
C8—C10 | 1.368 (7) | C24—H24 | 0.9300 |
C8—C9 | 1.374 (7) | C25—C26 | 1.387 (7) |
C8—O5 | 1.376 (5) | C25—H25 | 0.9300 |
C9—C12 | 1.366 (8) | C26—N2 | 1.319 (6) |
C9—H9 | 0.9300 | C26—H26 | 0.9300 |
C10—C11 | 1.410 (7) | C27—O4 | 1.249 (5) |
C10—H10 | 0.9300 | C27—O3 | 1.259 (5) |
C11—C13 | 1.361 (8) | O1—Ni1ii | 2.107 (3) |
C11—H11 | 0.9300 | O4—Ni1iii | 2.054 (3) |
C12—C13 | 1.353 (8) | O6—H6 | 0.8200 |
C12—H12 | 0.9300 | O8—H8A | 0.8200 |
C13—C14 | 1.546 (8) | O8—H8B | 0.8282 |
C14—O7A | 1.244 (13) | O7A—O7B | 0.760 (15) |
C14—O6 | 1.260 (8) | | |
| | | |
O2—Ni1—O4i | 90.29 (11) | O6—C14—C13 | 113.0 (6) |
O2—Ni1—N2 | 169.75 (13) | O7B—C14—C13 | 117.5 (8) |
O4i—Ni1—N2 | 91.42 (12) | N1—C15—C16 | 123.1 (5) |
O2—Ni1—N1 | 89.71 (13) | N1—C15—H15 | 118.5 |
O4i—Ni1—N1 | 89.01 (12) | C16—C15—H15 | 118.5 |
N2—Ni1—N1 | 80.22 (14) | C17—C16—C15 | 118.3 (6) |
O2—Ni1—O8 | 93.38 (11) | C17—C16—H16 | 120.9 |
O4i—Ni1—O8 | 88.53 (11) | C15—C16—H16 | 120.9 |
N2—Ni1—O8 | 96.76 (13) | C16—C17—C18 | 120.8 (5) |
N1—Ni1—O8 | 176.05 (13) | C16—C17—H17 | 119.6 |
O2—Ni1—O1ii | 94.58 (11) | C18—C17—H17 | 119.6 |
O4i—Ni1—O1ii | 174.43 (11) | C19—C18—C17 | 116.6 (5) |
N2—Ni1—O1ii | 84.27 (12) | C19—C18—C20 | 118.0 (6) |
N1—Ni1—O1ii | 93.72 (12) | C17—C18—C20 | 125.4 (6) |
O8—Ni1—O1ii | 88.48 (10) | N1—C19—C18 | 123.1 (5) |
O1—C1—O2 | 125.8 (3) | N1—C19—C22 | 116.6 (4) |
O1—C1—C2 | 118.6 (3) | C18—C19—C22 | 120.3 (5) |
O2—C1—C2 | 115.4 (3) | C21—C20—C18 | 121.9 (6) |
C4—C2—C3 | 119.2 (4) | C21—C20—H20 | 119.0 |
C4—C2—C1 | 121.7 (4) | C18—C20—H20 | 119.0 |
C3—C2—C1 | 119.0 (4) | C20—C21—C23 | 121.5 (6) |
C5—C3—C2 | 119.7 (4) | C20—C21—H21 | 119.2 |
C5—C3—H3 | 120.1 | C23—C21—H21 | 119.2 |
C2—C3—H3 | 120.1 | N2—C22—C23 | 122.7 (5) |
C7—C4—C2 | 121.2 (4) | N2—C22—C19 | 117.2 (4) |
C7—C4—H4 | 119.4 | C23—C22—C19 | 120.0 (5) |
C2—C4—H4 | 119.4 | C24—C23—C22 | 117.4 (5) |
C3—C5—O5 | 120.0 (4) | C24—C23—C21 | 124.3 (6) |
C3—C5—C6 | 121.1 (4) | C22—C23—C21 | 118.2 (6) |
O5—C5—C6 | 118.7 (3) | C25—C24—C23 | 119.3 (5) |
C5—C6—C7 | 118.9 (4) | C25—C24—H24 | 120.4 |
C5—C6—C27 | 120.6 (4) | C23—C24—H24 | 120.4 |
C7—C6—C27 | 120.4 (4) | C24—C25—C26 | 120.0 (6) |
C4—C7—C6 | 119.7 (4) | C24—C25—H25 | 120.0 |
C4—C7—H7 | 120.1 | C26—C25—H25 | 120.0 |
C6—C7—H7 | 120.1 | N2—C26—C25 | 122.7 (5) |
C10—C8—C9 | 121.5 (5) | N2—C26—H26 | 118.7 |
C10—C8—O5 | 123.0 (4) | C25—C26—H26 | 118.7 |
C9—C8—O5 | 115.4 (5) | O4—C27—O3 | 125.2 (4) |
C12—C9—C8 | 119.6 (6) | O4—C27—C6 | 116.4 (3) |
C12—C9—H9 | 120.2 | O3—C27—C6 | 118.4 (3) |
C8—C9—H9 | 120.2 | C15—N1—C19 | 118.1 (4) |
C8—C10—C11 | 117.7 (5) | C15—N1—Ni1 | 128.9 (3) |
C8—C10—H10 | 121.1 | C19—N1—Ni1 | 113.0 (3) |
C11—C10—H10 | 121.1 | C26—N2—C22 | 117.9 (4) |
C13—C11—C10 | 119.9 (5) | C26—N2—Ni1 | 129.0 (3) |
C13—C11—H11 | 120.1 | C22—N2—Ni1 | 113.0 (3) |
C10—C11—H11 | 120.1 | C1—O1—Ni1ii | 122.4 (2) |
C13—C12—C9 | 120.1 (6) | C1—O2—Ni1 | 135.1 (3) |
C13—C12—H12 | 119.9 | C27—O4—Ni1iii | 129.1 (3) |
C9—C12—H12 | 119.9 | C8—O5—C5 | 119.0 (3) |
C12—C13—C11 | 121.1 (5) | C14—O6—H6 | 109.5 |
C12—C13—C14 | 117.9 (6) | Ni1—O8—H8A | 109.6 |
C11—C13—C14 | 120.9 (6) | Ni1—O8—H8B | 100.8 |
O7A—C14—O6 | 124.1 (9) | H8A—O8—H8B | 104.4 |
O7A—C14—O7B | 35.3 (7) | O7B—O7A—C14 | 74.0 (16) |
O6—C14—O7B | 125.6 (8) | O7A—O7B—C14 | 70.8 (15) |
O7A—C14—C13 | 119.7 (9) | | |
| | | |
O1—C1—C2—C4 | −25.3 (6) | N1—C19—C22—N2 | −1.6 (6) |
O2—C1—C2—C4 | 150.4 (4) | C18—C19—C22—N2 | 178.9 (4) |
O1—C1—C2—C3 | 158.7 (4) | N1—C19—C22—C23 | 177.5 (4) |
O2—C1—C2—C3 | −25.5 (5) | C18—C19—C22—C23 | −2.0 (6) |
C4—C2—C3—C5 | −0.2 (6) | N2—C22—C23—C24 | 0.4 (7) |
C1—C2—C3—C5 | 175.8 (4) | C19—C22—C23—C24 | −178.7 (4) |
C3—C2—C4—C7 | 2.3 (6) | N2—C22—C23—C21 | −179.8 (4) |
C1—C2—C4—C7 | −173.6 (4) | C19—C22—C23—C21 | 1.1 (7) |
C2—C3—C5—O5 | 170.4 (4) | C20—C21—C23—C24 | 178.9 (6) |
C2—C3—C5—C6 | −3.4 (6) | C20—C21—C23—C22 | −0.9 (9) |
C3—C5—C6—C7 | 5.0 (6) | C22—C23—C24—C25 | 0.6 (8) |
O5—C5—C6—C7 | −168.9 (4) | C21—C23—C24—C25 | −179.2 (6) |
C3—C5—C6—C27 | −171.6 (4) | C23—C24—C25—C26 | −0.9 (9) |
O5—C5—C6—C27 | 14.6 (5) | C24—C25—C26—N2 | 0.2 (8) |
C2—C4—C7—C6 | −0.7 (6) | C5—C6—C27—O4 | 44.1 (5) |
C5—C6—C7—C4 | −2.9 (6) | C7—C6—C27—O4 | −132.4 (4) |
C27—C6—C7—C4 | 173.6 (4) | C5—C6—C27—O3 | −136.8 (4) |
C10—C8—C9—C12 | 0.3 (9) | C7—C6—C27—O3 | 46.7 (6) |
O5—C8—C9—C12 | −176.6 (5) | C16—C15—N1—C19 | 0.6 (7) |
C9—C8—C10—C11 | −0.5 (7) | C16—C15—N1—Ni1 | 178.6 (4) |
O5—C8—C10—C11 | 176.2 (4) | C18—C19—N1—C15 | −1.9 (6) |
C8—C10—C11—C13 | 0.4 (8) | C22—C19—N1—C15 | 178.5 (4) |
C8—C9—C12—C13 | 0.0 (10) | C18—C19—N1—Ni1 | 179.7 (3) |
C9—C12—C13—C11 | −0.1 (11) | C22—C19—N1—Ni1 | 0.2 (5) |
C9—C12—C13—C14 | 176.1 (6) | C25—C26—N2—C22 | 0.8 (7) |
C10—C11—C13—C12 | −0.1 (9) | C25—C26—N2—Ni1 | 176.0 (4) |
C10—C11—C13—C14 | −176.2 (5) | C23—C22—N2—C26 | −1.0 (6) |
C12—C13—C14—O7A | 19.1 (12) | C19—C22—N2—C26 | 178.0 (4) |
C11—C13—C14—O7A | −164.6 (9) | C23—C22—N2—Ni1 | −177.0 (3) |
C12—C13—C14—O6 | 179.8 (6) | C19—C22—N2—Ni1 | 2.1 (5) |
C11—C13—C14—O6 | −4.0 (9) | O2—C1—O1—Ni1ii | −42.5 (5) |
C12—C13—C14—O7B | −21.2 (12) | C2—C1—O1—Ni1ii | 132.7 (3) |
C11—C13—C14—O7B | 155.1 (9) | O1—C1—O2—Ni1 | −59.0 (6) |
N1—C15—C16—C17 | 0.2 (9) | C2—C1—O2—Ni1 | 125.6 (3) |
C15—C16—C17—C18 | 0.3 (9) | O3—C27—O4—Ni1iii | −5.5 (6) |
C16—C17—C18—C19 | −1.5 (8) | C6—C27—O4—Ni1iii | 173.6 (3) |
C16—C17—C18—C20 | 177.8 (6) | C10—C8—O5—C5 | 36.6 (6) |
C17—C18—C19—N1 | 2.3 (7) | C9—C8—O5—C5 | −146.5 (4) |
C20—C18—C19—N1 | −177.0 (4) | C3—C5—O5—C8 | 59.1 (5) |
C17—C18—C19—C22 | −178.1 (4) | C6—C5—O5—C8 | −127.0 (4) |
C20—C18—C19—C22 | 2.5 (7) | O6—C14—O7A—O7B | 105.1 (17) |
C19—C18—C20—C21 | −2.4 (9) | C13—C14—O7A—O7B | −96.5 (17) |
C17—C18—C20—C21 | 178.4 (6) | O6—C14—O7B—O7A | −100.5 (18) |
C18—C20—C21—C23 | 1.6 (10) | C13—C14—O7B—O7A | 103.4 (16) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y+1, −z+1; (iii) 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 |
C15—H15···O2 | 0.93 | 2.54 | 3.063 (6) | 116 |
O6—H6···O3iv | 0.82 | 1.91 | 2.638 (5) | 147 |
O8—H8A···O3i | 0.82 | 1.92 | 2.661 (4) | 149 |
O8—H8B···O1 | 0.83 | 2.65 | 3.247 (4) | 130 |
O8—H8B···O2ii | 0.83 | 2.08 | 2.762 (4) | 140 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y+1, −z+1; (iv) x+1, y, z. |