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Two three-dimensional cobalt-based metal–organic frameworks with 5-(hydroxymethyl)isophthalic acid (H2HIPA), namely poly[[μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N3:N3′][μ2-5-(hydroxymethyl)isophthalato-κ2O1:O3]cobalt(II)], [Co(C9H6O5)(C14H14N4)]n (1), and poly[tris[μ2-1,4-bis(1H-imidazol-1-yl)benzene-κ2N3:N3′]bis[μ3-5-(hydroxymethyl)isophthalato-κ2O1:O3:O5]dicobalt(II)], [Co2(C9H6O5)2(C12H10N4)3]n (2), were synthesized under similar hydrothermal conditions. Single-crystal X-ray diffraction analyses revealed that 5-(hydroxymethyl)isophthalate (HIPA2−) and 1,4-bis(2-methyl-1H-imidazol-1-yl)benzene (1,4-BMIB) are simple linkers connecting cobalt centres to build a fourfold interpenetration dia framework in complex 1. However, complex 2 is a pillared-layer framework with a (3,6)-connected network constructed by 1,4-bis(1H-imidazol-1-yl)benzene (1,4-DIB) linkers, 3-connected HIPA2− ligands and 6-connected CoII centres. The above significant structural differences can be ascribed to the introduction of the different auxiliary N-donor ligands. Moreover, UV–Vis spectroscopy and Mott–Schottky measurements confirmed that complexes 1 and 2 are typical n-type semiconductors.
Supporting information
CCDC references: 1977352; 1977351
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Poly[[µ
2-1,4-bis(2-methyl-1
H-imidazol-1-yl)benzene-
κ2N3:
N3'][µ
2-5-(hydroxymethyl)isophthalato-
κ2O1:
O3]cobalt(II)] (1)
top
Crystal data top
[Co(C9H6O5)(C14H14N4)] | Dx = 1.388 Mg m−3 |
Mr = 491.36 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Ibca | Cell parameters from 6718 reflections |
a = 17.1976 (10) Å | θ = 4.5–30.2° |
b = 16.7629 (9) Å | µ = 0.77 mm−1 |
c = 16.3162 (10) Å | T = 295 K |
V = 4703.7 (5) Å3 | Block, clear light colourless |
Z = 8 | 0.2 × 0.2 × 0.15 mm |
F(000) = 2024 | |
Data collection top
Rigaku 003 diffractometer | 3198 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2615 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 30.3°, θmin = 4.2° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −24→19 |
Tmin = 0.611, Tmax = 1.000 | k = −23→21 |
14797 measured reflections | l = −21→20 |
Refinement top
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0577P)2 + 1.7017P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3198 reflections | Δρmax = 0.39 e Å−3 |
158 parameters | Δρmin = −0.38 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) |
Co1 | 0.56110 (2) | 0.500000 | 0.250000 | 0.02278 (10) | |
O1 | 0.61338 (7) | 0.56154 (7) | 0.33544 (7) | 0.0447 (3) | |
O2 | 0.65793 (9) | 0.44750 (8) | 0.38295 (11) | 0.0676 (5) | |
O3 | 0.66849 (10) | 0.80932 (13) | 0.5103 (2) | 0.0508 (6) | 0.5 |
H3 | 0.666855 | 0.848525 | 0.540322 | 0.076* | 0.5 |
N1 | 0.48553 (7) | 0.41496 (7) | 0.29050 (8) | 0.0321 (3) | |
N2 | 0.38453 (7) | 0.33508 (7) | 0.29418 (8) | 0.0331 (3) | |
C1 | 0.65544 (8) | 0.52094 (10) | 0.38427 (10) | 0.0346 (3) | |
C2 | 0.70364 (8) | 0.56757 (8) | 0.44451 (9) | 0.0287 (3) | |
C3 | 0.750000 | 0.52628 (12) | 0.500000 | 0.0319 (4) | |
H3A | 0.750002 | 0.470798 | 0.500000 | 0.038* | |
C4 | 0.70389 (8) | 0.65096 (8) | 0.44477 (8) | 0.0290 (3) | |
H4 | 0.672902 | 0.678537 | 0.407624 | 0.035* | |
C5 | 0.750000 | 0.69337 (11) | 0.500000 | 0.0291 (4) | |
C6 | 0.750000 | 0.78376 (12) | 0.500000 | 0.0439 (5) | |
H6B | 0.781715 | 0.803884 | 0.544605 | 0.053* | 0.5 |
H6A | 0.770794 | 0.803883 | 0.448749 | 0.053* | 0.5 |
C7 | 0.48053 (9) | 0.38138 (10) | 0.36757 (10) | 0.0413 (4) | |
H7 | 0.514461 | 0.391300 | 0.410762 | 0.050* | |
C8 | 0.41858 (10) | 0.33181 (11) | 0.37043 (11) | 0.0461 (4) | |
H8 | 0.402243 | 0.301558 | 0.414996 | 0.055* | |
C9 | 0.42686 (9) | 0.38562 (11) | 0.24724 (9) | 0.0350 (3) | |
C10 | 0.41145 (14) | 0.40255 (17) | 0.15932 (12) | 0.0743 (8) | |
H10A | 0.373266 | 0.444102 | 0.154886 | 0.111* | |
H10B | 0.392413 | 0.355167 | 0.133075 | 0.111* | |
H10C | 0.458728 | 0.419333 | 0.133213 | 0.111* | |
C11 | 0.31592 (8) | 0.29163 (9) | 0.27027 (10) | 0.0310 (3) | |
C12 | 0.31432 (8) | 0.20970 (9) | 0.28126 (11) | 0.0351 (3) | |
H12 | 0.357445 | 0.183224 | 0.302300 | 0.042* | |
C13 | 0.25234 (9) | 0.33247 (9) | 0.23946 (10) | 0.0361 (3) | |
H13 | 0.254263 | 0.387527 | 0.232705 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.01881 (14) | 0.02342 (14) | 0.02609 (15) | 0.000 | 0.000 | −0.00293 (9) |
O1 | 0.0483 (7) | 0.0464 (6) | 0.0392 (6) | −0.0140 (5) | −0.0172 (5) | 0.0001 (5) |
O2 | 0.0612 (8) | 0.0378 (6) | 0.1040 (13) | 0.0067 (6) | −0.0362 (8) | −0.0303 (7) |
O3 | 0.0517 (13) | 0.0258 (11) | 0.0751 (19) | 0.0070 (10) | −0.0080 (13) | −0.0052 (11) |
N1 | 0.0283 (6) | 0.0363 (6) | 0.0315 (6) | −0.0097 (5) | 0.0010 (4) | −0.0011 (5) |
N2 | 0.0263 (6) | 0.0355 (6) | 0.0376 (7) | −0.0094 (5) | −0.0001 (5) | 0.0020 (5) |
C1 | 0.0274 (7) | 0.0392 (7) | 0.0371 (8) | −0.0026 (6) | −0.0040 (6) | −0.0127 (6) |
C2 | 0.0278 (6) | 0.0280 (6) | 0.0303 (6) | −0.0005 (5) | −0.0059 (5) | −0.0059 (5) |
C3 | 0.0320 (9) | 0.0225 (8) | 0.0410 (11) | 0.000 | −0.0058 (8) | 0.000 |
C4 | 0.0317 (6) | 0.0289 (6) | 0.0265 (6) | 0.0027 (5) | −0.0076 (5) | 0.0017 (5) |
C5 | 0.0344 (9) | 0.0227 (8) | 0.0303 (9) | 0.000 | −0.0051 (8) | 0.000 |
C6 | 0.0534 (13) | 0.0224 (9) | 0.0559 (14) | 0.000 | −0.0123 (11) | 0.000 |
C7 | 0.0334 (8) | 0.0552 (10) | 0.0354 (8) | −0.0125 (7) | −0.0050 (6) | 0.0080 (7) |
C8 | 0.0368 (8) | 0.0595 (11) | 0.0420 (9) | −0.0156 (8) | −0.0043 (7) | 0.0165 (8) |
C9 | 0.0326 (7) | 0.0400 (8) | 0.0325 (7) | −0.0145 (6) | 0.0009 (5) | −0.0008 (6) |
C10 | 0.0784 (14) | 0.1073 (19) | 0.0373 (10) | −0.0612 (14) | −0.0117 (10) | 0.0091 (11) |
C11 | 0.0241 (6) | 0.0319 (7) | 0.0369 (7) | −0.0079 (5) | 0.0016 (5) | 0.0010 (6) |
C12 | 0.0264 (7) | 0.0314 (7) | 0.0474 (9) | −0.0014 (5) | −0.0026 (6) | 0.0040 (6) |
C13 | 0.0319 (7) | 0.0255 (7) | 0.0508 (9) | −0.0044 (6) | −0.0012 (6) | 0.0031 (6) |
Geometric parameters (Å, º) top
Co1—O1 | 1.9534 (11) | C4—H4 | 0.9300 |
Co1—O1i | 1.9534 (11) | C4—C5 | 1.3951 (16) |
Co1—N1 | 2.0391 (11) | C5—C6 | 1.515 (3) |
Co1—N1i | 2.0391 (11) | C6—H6B | 0.9700 |
O1—C1 | 1.273 (2) | C6—H6A | 0.9700 |
O2—C1 | 1.232 (2) | C7—H7 | 0.9300 |
O3—H3 | 0.8200 | C7—C8 | 1.352 (2) |
O3—C6 | 1.4755 (16) | C8—H8 | 0.9300 |
N1—C7 | 1.380 (2) | C9—C10 | 1.486 (2) |
N1—C9 | 1.3259 (18) | C10—H10A | 0.9600 |
N2—C8 | 1.376 (2) | C10—H10B | 0.9600 |
N2—C9 | 1.3543 (19) | C10—H10C | 0.9600 |
N2—C11 | 1.4405 (17) | C11—C12 | 1.385 (2) |
C1—C2 | 1.5048 (18) | C11—C13 | 1.384 (2) |
C2—C3 | 1.3909 (17) | C12—H12 | 0.9300 |
C2—C4 | 1.3978 (19) | C12—C13ii | 1.389 (2) |
C3—H3A | 0.9300 | C13—H13 | 0.9300 |
| | | |
O1—Co1—O1i | 125.19 (8) | O3—C6—H6B | 110.3 |
O1—Co1—N1i | 98.94 (5) | O3—C6—H6A | 110.3 |
O1—Co1—N1 | 115.55 (5) | C5—C6—H6B | 110.3 |
O1i—Co1—N1i | 115.55 (5) | C5—C6—H6A | 110.3 |
O1i—Co1—N1 | 98.94 (5) | H6B—C6—H6A | 108.6 |
N1i—Co1—N1 | 100.80 (7) | N1—C7—H7 | 125.3 |
C1—O1—Co1 | 115.20 (10) | C8—C7—N1 | 109.34 (14) |
C6—O3—H3 | 109.5 | C8—C7—H7 | 125.3 |
C7—N1—Co1 | 128.31 (10) | N2—C8—H8 | 126.9 |
C9—N1—Co1 | 124.88 (10) | C7—C8—N2 | 106.24 (14) |
C9—N1—C7 | 106.63 (12) | C7—C8—H8 | 126.9 |
C8—N2—C11 | 124.97 (13) | N1—C9—N2 | 109.88 (13) |
C9—N2—C8 | 107.91 (12) | N1—C9—C10 | 125.35 (14) |
C9—N2—C11 | 127.12 (13) | N2—C9—C10 | 124.72 (14) |
O1—C1—C2 | 116.36 (13) | C9—C10—H10A | 109.5 |
O2—C1—O1 | 122.89 (14) | C9—C10—H10B | 109.5 |
O2—C1—C2 | 120.75 (14) | C9—C10—H10C | 109.5 |
C3—C2—C1 | 118.84 (13) | H10A—C10—H10B | 109.5 |
C3—C2—C4 | 119.60 (13) | H10A—C10—H10C | 109.5 |
C4—C2—C1 | 121.54 (13) | H10B—C10—H10C | 109.5 |
C2iii—C3—C2 | 120.30 (18) | C12—C11—N2 | 118.84 (13) |
C2—C3—H3A | 119.8 | C13—C11—N2 | 119.69 (14) |
C2iii—C3—H3A | 119.8 | C13—C11—C12 | 121.44 (13) |
C2—C4—H4 | 119.6 | C11—C12—H12 | 120.3 |
C5—C4—C2 | 120.88 (13) | C11—C12—C13ii | 119.32 (14) |
C5—C4—H4 | 119.6 | C13ii—C12—H12 | 120.3 |
C4iii—C5—C4 | 118.73 (17) | C11—C13—C12ii | 119.25 (14) |
C4—C5—C6 | 120.63 (9) | C11—C13—H13 | 120.4 |
C4iii—C5—C6 | 120.63 (9) | C12ii—C13—H13 | 120.4 |
O3—C6—C5 | 106.88 (12) | | |
| | | |
Co1—O1—C1—O2 | −6.3 (2) | C4iii—C5—C6—O3 | −124.50 (14) |
Co1—O1—C1—C2 | 173.17 (10) | C4—C5—C6—O3 | 55.50 (14) |
Co1—N1—C7—C8 | 175.30 (13) | C7—N1—C9—N2 | 0.40 (19) |
Co1—N1—C9—N2 | −175.15 (10) | C7—N1—C9—C10 | −177.1 (2) |
Co1—N1—C9—C10 | 7.3 (3) | C8—N2—C9—N1 | −0.6 (2) |
O1—C1—C2—C3 | 179.24 (12) | C8—N2—C9—C10 | 176.9 (2) |
O1—C1—C2—C4 | −2.0 (2) | C8—N2—C11—C12 | −53.7 (2) |
O2—C1—C2—C3 | −1.3 (2) | C8—N2—C11—C13 | 124.20 (19) |
O2—C1—C2—C4 | 177.44 (16) | C9—N1—C7—C8 | −0.1 (2) |
N1—C7—C8—N2 | −0.3 (2) | C9—N2—C8—C7 | 0.5 (2) |
N2—C11—C12—C13ii | 178.22 (15) | C9—N2—C11—C12 | 126.24 (18) |
N2—C11—C13—C12ii | −178.21 (15) | C9—N2—C11—C13 | −55.8 (2) |
C1—C2—C3—C2iii | 178.80 (14) | C11—N2—C8—C7 | −179.48 (15) |
C1—C2—C4—C5 | −178.79 (12) | C11—N2—C9—N1 | 179.42 (14) |
C2—C4—C5—C4iii | 0.02 (10) | C11—N2—C9—C10 | −3.1 (3) |
C2—C4—C5—C6 | −179.98 (10) | C12—C11—C13—C12ii | −0.3 (3) |
C3—C2—C4—C5 | −0.05 (19) | C13—C11—C12—C13ii | 0.3 (3) |
C4—C2—C3—C2iii | 0.02 (10) | | |
Symmetry codes: (i) x, −y+1, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1/2; (iii) −x+3/2, y, −z+1. |
Poly[tris[µ
2-1,4-bis(1
H-imidazol-1-yl)benzene-
κ2N3:
N3']bis[µ
3-5-(hydroxymethyl)isophthalato-
κ2O1:
O3:
O5]dicobalt(II)] (2)
top
Crystal data top
[Co2(C9H6O5)2(C12H10N4)3] | F(000) = 1168 |
Mr = 1136.86 | Dx = 1.528 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0331 (4) Å | Cell parameters from 3691 reflections |
b = 17.6045 (11) Å | θ = 2.6–27.8° |
c = 17.6523 (9) Å | µ = 0.75 mm−1 |
β = 98.077 (4)° | T = 295 K |
V = 2471.6 (2) Å3 | Block, clear light colourless |
Z = 2 | 0.3 × 0.3 × 0.3 mm |
Data collection top
Rigaku Oxford Diffraction four-circle diffractometer | 5127 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 3727 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 16.2083 pixels mm-1 | θmax = 28.5°, θmin = 2.3° |
ω scans | h = −10→7 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −23→14 |
Tmin = 0.691, Tmax = 1.000 | l = −23→21 |
11072 measured reflections | |
Refinement top
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0389P)2 + 0.444P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5127 reflections | Δρmax = 0.34 e Å−3 |
353 parameters | Δρmin = −0.34 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 | 0.77941 (3) | 0.74899 (2) | 0.75481 (2) | 0.01846 (10) | |
O4 | −0.06834 (18) | 0.76592 (10) | 0.35833 (9) | 0.0280 (4) | |
O5 | −0.00473 (18) | 0.79399 (11) | 0.70503 (9) | 0.0318 (4) | |
H5 | 0.061163 | 0.807427 | 0.742362 | 0.048* | |
O3 | 0.15764 (19) | 0.69704 (11) | 0.34424 (9) | 0.0345 (5) | |
O1 | 0.6208 (2) | 0.76690 (11) | 0.65661 (9) | 0.0388 (5) | |
O2 | 0.67104 (19) | 0.74757 (10) | 0.53708 (9) | 0.0321 (4) | |
N3 | 0.5871 (2) | 0.69188 (12) | 0.80706 (11) | 0.0276 (5) | |
N1 | 0.7021 (2) | 0.85640 (12) | 0.79070 (11) | 0.0275 (5) | |
N2 | 0.5951 (2) | 0.93655 (12) | 0.86666 (11) | 0.0301 (5) | |
N5 | 0.8597 (2) | 0.64134 (13) | 0.72094 (11) | 0.0303 (5) | |
N4 | 0.4924 (2) | 0.60671 (13) | 0.88200 (12) | 0.0311 (5) | |
N6 | 0.9377 (3) | 0.55818 (12) | 0.64039 (12) | 0.0323 (5) | |
C8 | 0.0755 (3) | 0.73935 (14) | 0.38136 (12) | 0.0207 (5) | |
C7 | 0.2895 (3) | 0.80249 (14) | 0.60943 (12) | 0.0224 (5) | |
H7 | 0.336547 | 0.815761 | 0.658825 | 0.027* | |
C6 | 0.1179 (3) | 0.81217 (14) | 0.58683 (12) | 0.0213 (5) | |
C2 | 0.3917 (3) | 0.77319 (14) | 0.55905 (12) | 0.0210 (5) | |
C4 | 0.1507 (3) | 0.76232 (13) | 0.46154 (12) | 0.0197 (5) | |
C5 | 0.0499 (3) | 0.79172 (14) | 0.51309 (12) | 0.0230 (5) | |
H5A | −0.064901 | 0.797654 | 0.497602 | 0.028* | |
C3 | 0.3220 (3) | 0.75341 (13) | 0.48505 (12) | 0.0200 (5) | |
H3 | 0.390283 | 0.734150 | 0.451212 | 0.024* | |
C18 | 0.6214 (3) | 0.65161 (16) | 0.86930 (14) | 0.0321 (6) | |
H18 | 0.723622 | 0.653666 | 0.901348 | 0.039* | |
C1 | 0.5782 (3) | 0.76154 (14) | 0.58532 (13) | 0.0222 (5) | |
C9 | 0.0084 (3) | 0.84402 (15) | 0.64257 (12) | 0.0276 (6) | |
H9A | 0.055087 | 0.892055 | 0.662378 | 0.033* | |
H9B | −0.103132 | 0.853814 | 0.615515 | 0.033* | |
C24 | 0.8896 (3) | 0.62984 (15) | 0.65083 (14) | 0.0296 (6) | |
H24 | 0.878681 | 0.666884 | 0.612903 | 0.036* | |
C12 | 0.6777 (3) | 0.87091 (15) | 0.86120 (14) | 0.0314 (6) | |
H12 | 0.713535 | 0.839412 | 0.902586 | 0.038* | |
C13 | 0.5463 (3) | 0.96915 (15) | 0.93411 (13) | 0.0282 (6) | |
C25 | 0.9716 (3) | 0.52739 (15) | 0.56917 (14) | 0.0300 (6) | |
C15 | 0.5490 (3) | 0.92528 (15) | 0.99926 (14) | 0.0338 (6) | |
H15 | 0.581586 | 0.874619 | 0.998628 | 0.041* | |
C27 | 1.0491 (3) | 0.57265 (16) | 0.52123 (15) | 0.0371 (7) | |
H27 | 1.082007 | 0.621709 | 0.536053 | 0.044* | |
C19 | 0.4951 (3) | 0.55267 (15) | 0.94203 (15) | 0.0334 (6) | |
C26 | 0.9221 (3) | 0.45481 (15) | 0.54903 (15) | 0.0372 (7) | |
H26 | 0.870154 | 0.424624 | 0.582048 | 0.045* | |
C16 | 0.4246 (3) | 0.67273 (16) | 0.77809 (15) | 0.0376 (7) | |
H16 | 0.364760 | 0.692540 | 0.733537 | 0.045* | |
C17 | 0.3650 (3) | 0.62138 (17) | 0.82342 (16) | 0.0423 (7) | |
H17 | 0.258214 | 0.599857 | 0.816573 | 0.051* | |
C10 | 0.6297 (4) | 0.91499 (17) | 0.74806 (16) | 0.0464 (8) | |
H10 | 0.626816 | 0.920009 | 0.695449 | 0.056* | |
C23 | 0.9395 (4) | 0.52144 (18) | 0.70851 (16) | 0.0488 (8) | |
H23 | 0.967695 | 0.470941 | 0.719140 | 0.059* | |
C14 | 0.4965 (3) | 1.04378 (15) | 0.93477 (14) | 0.0339 (6) | |
H14 | 0.493361 | 1.073338 | 0.890931 | 0.041* | |
C22 | 0.8918 (4) | 0.57350 (18) | 0.75732 (16) | 0.0464 (8) | |
H22 | 0.882198 | 0.564400 | 0.808420 | 0.056* | |
C11 | 0.5626 (4) | 0.96484 (18) | 0.79337 (15) | 0.0523 (9) | |
H11 | 0.505677 | 1.009488 | 0.778094 | 0.063* | |
C20 | 0.3556 (4) | 0.54086 (19) | 0.97643 (18) | 0.0534 (9) | |
H20 | 0.257538 | 0.568031 | 0.960793 | 0.064* | |
C21 | 0.6386 (4) | 0.51194 (19) | 0.96518 (18) | 0.0553 (9) | |
H21 | 0.733335 | 0.519868 | 0.941355 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.01510 (16) | 0.0282 (2) | 0.01141 (16) | 0.00229 (13) | −0.00033 (11) | −0.00315 (13) |
O4 | 0.0202 (8) | 0.0459 (12) | 0.0156 (8) | 0.0054 (8) | −0.0058 (6) | −0.0035 (8) |
O5 | 0.0227 (8) | 0.0586 (13) | 0.0138 (8) | −0.0056 (9) | 0.0013 (6) | 0.0030 (8) |
O3 | 0.0307 (9) | 0.0510 (13) | 0.0198 (9) | 0.0108 (9) | −0.0035 (7) | −0.0105 (9) |
O1 | 0.0267 (9) | 0.0664 (15) | 0.0198 (9) | 0.0133 (9) | −0.0091 (7) | −0.0087 (9) |
O2 | 0.0185 (8) | 0.0516 (13) | 0.0264 (9) | 0.0025 (8) | 0.0041 (7) | −0.0023 (9) |
N3 | 0.0252 (10) | 0.0333 (13) | 0.0248 (11) | −0.0023 (10) | 0.0054 (8) | 0.0008 (10) |
N1 | 0.0299 (10) | 0.0295 (13) | 0.0236 (11) | 0.0050 (10) | 0.0053 (8) | −0.0050 (10) |
N2 | 0.0381 (12) | 0.0280 (13) | 0.0254 (11) | 0.0067 (10) | 0.0091 (9) | −0.0024 (10) |
N5 | 0.0354 (11) | 0.0337 (14) | 0.0224 (11) | 0.0070 (10) | 0.0061 (9) | −0.0048 (10) |
N4 | 0.0304 (11) | 0.0325 (14) | 0.0321 (12) | −0.0047 (10) | 0.0109 (9) | 0.0002 (10) |
N6 | 0.0432 (12) | 0.0278 (13) | 0.0277 (12) | 0.0086 (11) | 0.0108 (9) | −0.0013 (10) |
C8 | 0.0190 (11) | 0.0293 (15) | 0.0128 (11) | −0.0040 (10) | −0.0011 (9) | −0.0001 (10) |
C7 | 0.0243 (11) | 0.0307 (15) | 0.0108 (11) | −0.0033 (11) | −0.0019 (9) | −0.0019 (10) |
C6 | 0.0210 (11) | 0.0282 (14) | 0.0150 (11) | 0.0015 (10) | 0.0042 (9) | 0.0013 (10) |
C2 | 0.0160 (10) | 0.0284 (14) | 0.0171 (11) | −0.0004 (10) | −0.0024 (9) | 0.0011 (10) |
C4 | 0.0196 (11) | 0.0276 (14) | 0.0111 (10) | −0.0023 (10) | −0.0014 (9) | 0.0017 (10) |
C5 | 0.0157 (10) | 0.0349 (15) | 0.0178 (12) | −0.0009 (11) | 0.0000 (9) | 0.0037 (11) |
C3 | 0.0178 (10) | 0.0270 (14) | 0.0152 (11) | 0.0025 (10) | 0.0025 (8) | −0.0006 (10) |
C18 | 0.0283 (13) | 0.0406 (17) | 0.0279 (14) | −0.0084 (12) | 0.0057 (10) | −0.0014 (13) |
C1 | 0.0176 (11) | 0.0265 (15) | 0.0211 (12) | −0.0007 (10) | −0.0023 (9) | −0.0033 (10) |
C9 | 0.0272 (12) | 0.0391 (17) | 0.0169 (12) | 0.0039 (12) | 0.0040 (9) | −0.0009 (11) |
C24 | 0.0381 (14) | 0.0245 (15) | 0.0266 (14) | 0.0058 (12) | 0.0058 (11) | −0.0015 (11) |
C12 | 0.0373 (14) | 0.0329 (16) | 0.0232 (13) | 0.0113 (13) | 0.0012 (11) | −0.0058 (12) |
C13 | 0.0343 (13) | 0.0274 (15) | 0.0241 (13) | 0.0055 (12) | 0.0082 (10) | −0.0046 (11) |
C25 | 0.0376 (14) | 0.0254 (14) | 0.0287 (14) | 0.0083 (12) | 0.0111 (11) | −0.0025 (12) |
C15 | 0.0496 (16) | 0.0214 (14) | 0.0318 (15) | 0.0091 (13) | 0.0107 (12) | −0.0015 (12) |
C27 | 0.0499 (16) | 0.0213 (14) | 0.0436 (17) | −0.0006 (13) | 0.0192 (13) | −0.0084 (13) |
C19 | 0.0371 (14) | 0.0307 (16) | 0.0350 (15) | −0.0054 (13) | 0.0142 (11) | 0.0008 (12) |
C26 | 0.0515 (16) | 0.0269 (16) | 0.0382 (16) | 0.0018 (14) | 0.0242 (13) | 0.0003 (13) |
C16 | 0.0292 (13) | 0.0438 (19) | 0.0384 (16) | −0.0028 (13) | −0.0002 (11) | 0.0054 (14) |
C17 | 0.0263 (13) | 0.0446 (19) | 0.0546 (19) | −0.0094 (13) | 0.0007 (13) | 0.0032 (15) |
C10 | 0.076 (2) | 0.0399 (19) | 0.0275 (15) | 0.0160 (16) | 0.0213 (14) | 0.0060 (14) |
C23 | 0.079 (2) | 0.0323 (18) | 0.0396 (17) | 0.0203 (16) | 0.0245 (15) | 0.0105 (14) |
C14 | 0.0483 (15) | 0.0277 (15) | 0.0272 (14) | 0.0071 (13) | 0.0104 (11) | 0.0025 (12) |
C22 | 0.069 (2) | 0.045 (2) | 0.0275 (15) | 0.0161 (17) | 0.0172 (14) | 0.0067 (14) |
C11 | 0.090 (2) | 0.0389 (19) | 0.0306 (16) | 0.0296 (18) | 0.0189 (15) | 0.0082 (14) |
C20 | 0.0372 (15) | 0.059 (2) | 0.067 (2) | 0.0041 (15) | 0.0199 (15) | 0.0236 (18) |
C21 | 0.0393 (16) | 0.064 (2) | 0.069 (2) | 0.0029 (16) | 0.0290 (15) | 0.0251 (18) |
Geometric parameters (Å, º) top
Co1—O4i | 2.0678 (14) | C2—C1 | 1.519 (3) |
Co1—O5ii | 2.1988 (16) | C4—C5 | 1.400 (3) |
Co1—O1 | 2.0267 (16) | C4—C3 | 1.389 (3) |
Co1—N3 | 2.1562 (19) | C5—H5A | 0.9300 |
Co1—N1 | 2.115 (2) | C3—H3 | 0.9300 |
Co1—N5 | 2.115 (2) | C18—H18 | 0.9300 |
O4—C8 | 1.260 (3) | C9—H9A | 0.9700 |
O5—H5 | 0.8200 | C9—H9B | 0.9700 |
O5—C9 | 1.427 (3) | C24—H24 | 0.9300 |
O3—C8 | 1.241 (3) | C12—H12 | 0.9300 |
O1—C1 | 1.260 (3) | C13—C15 | 1.383 (3) |
O2—C1 | 1.233 (3) | C13—C14 | 1.374 (3) |
N3—C18 | 1.304 (3) | C25—C27 | 1.373 (3) |
N3—C16 | 1.375 (3) | C25—C26 | 1.370 (3) |
N1—C12 | 1.312 (3) | C15—H15 | 0.9300 |
N1—C10 | 1.359 (3) | C15—C14iii | 1.380 (3) |
N2—C12 | 1.343 (3) | C27—H27 | 0.9300 |
N2—C13 | 1.425 (3) | C27—C26iv | 1.381 (3) |
N2—C11 | 1.377 (3) | C19—C20 | 1.363 (4) |
N5—C24 | 1.309 (3) | C19—C21 | 1.370 (4) |
N5—C22 | 1.363 (3) | C26—H26 | 0.9300 |
N4—C18 | 1.347 (3) | C16—H16 | 0.9300 |
N4—C19 | 1.422 (3) | C16—C17 | 1.339 (4) |
N4—C17 | 1.373 (3) | C17—H17 | 0.9300 |
N6—C24 | 1.340 (3) | C10—H10 | 0.9300 |
N6—C25 | 1.430 (3) | C10—C11 | 1.350 (4) |
N6—C23 | 1.364 (3) | C23—H23 | 0.9300 |
C8—C4 | 1.514 (3) | C23—C22 | 1.350 (4) |
C7—H7 | 0.9300 | C14—H14 | 0.9300 |
C7—C6 | 1.391 (3) | C22—H22 | 0.9300 |
C7—C2 | 1.392 (3) | C11—H11 | 0.9300 |
C6—C5 | 1.387 (3) | C20—H20 | 0.9300 |
C6—C9 | 1.516 (3) | C20—C21v | 1.384 (4) |
C2—C3 | 1.391 (3) | C21—H21 | 0.9300 |
| | | |
O4i—Co1—O5ii | 89.84 (6) | N4—C18—H18 | 123.8 |
O4i—Co1—N3 | 86.17 (7) | O1—C1—C2 | 114.4 (2) |
O4i—Co1—N1 | 90.62 (7) | O2—C1—O1 | 126.8 (2) |
O4i—Co1—N5 | 88.28 (7) | O2—C1—C2 | 118.8 (2) |
O1—Co1—O4i | 176.71 (7) | O5—C9—C6 | 112.7 (2) |
O1—Co1—O5ii | 92.20 (7) | O5—C9—H9A | 109.1 |
O1—Co1—N3 | 92.08 (8) | O5—C9—H9B | 109.1 |
O1—Co1—N1 | 86.64 (7) | C6—C9—H9A | 109.1 |
O1—Co1—N5 | 94.46 (7) | C6—C9—H9B | 109.1 |
N3—Co1—O5ii | 172.60 (7) | H9A—C9—H9B | 107.8 |
N1—Co1—O5ii | 94.52 (8) | N5—C24—N6 | 111.7 (2) |
N1—Co1—N3 | 91.75 (8) | N5—C24—H24 | 124.1 |
N1—Co1—N5 | 178.90 (8) | N6—C24—H24 | 124.1 |
N5—Co1—O5ii | 85.46 (8) | N1—C12—N2 | 112.1 (2) |
N5—Co1—N3 | 88.20 (8) | N1—C12—H12 | 123.9 |
C8—O4—Co1vi | 129.77 (15) | N2—C12—H12 | 123.9 |
Co1vii—O5—H5 | 103.8 | C15—C13—N2 | 119.7 (2) |
C9—O5—Co1vii | 132.81 (13) | C14—C13—N2 | 120.4 (2) |
C9—O5—H5 | 109.5 | C14—C13—C15 | 119.8 (2) |
C1—O1—Co1 | 153.14 (16) | C27—C25—N6 | 118.7 (2) |
C18—N3—Co1 | 122.30 (15) | C26—C25—N6 | 119.8 (2) |
C18—N3—C16 | 104.9 (2) | C26—C25—C27 | 121.4 (2) |
C16—N3—Co1 | 130.92 (17) | C13—C15—H15 | 119.8 |
C12—N1—Co1 | 123.20 (18) | C14iii—C15—C13 | 120.4 (2) |
C12—N1—C10 | 105.6 (2) | C14iii—C15—H15 | 119.8 |
C10—N1—Co1 | 129.33 (17) | C25—C27—H27 | 120.1 |
C12—N2—C13 | 127.1 (2) | C25—C27—C26iv | 119.9 (2) |
C12—N2—C11 | 105.9 (2) | C26iv—C27—H27 | 120.1 |
C11—N2—C13 | 127.0 (2) | C20—C19—N4 | 120.4 (2) |
C24—N5—Co1 | 120.63 (18) | C20—C19—C21 | 119.8 (3) |
C24—N5—C22 | 105.2 (2) | C21—C19—N4 | 119.7 (2) |
C22—N5—Co1 | 134.16 (17) | C25—C26—C27iv | 118.7 (2) |
C18—N4—C19 | 125.8 (2) | C25—C26—H26 | 120.6 |
C18—N4—C17 | 105.9 (2) | C27iv—C26—H26 | 120.6 |
C17—N4—C19 | 128.2 (2) | N3—C16—H16 | 125.0 |
C24—N6—C25 | 124.9 (2) | C17—C16—N3 | 110.1 (2) |
C24—N6—C23 | 107.0 (2) | C17—C16—H16 | 125.0 |
C23—N6—C25 | 128.0 (2) | N4—C17—H17 | 126.7 |
O4—C8—C4 | 115.5 (2) | C16—C17—N4 | 106.6 (2) |
O3—C8—O4 | 125.7 (2) | C16—C17—H17 | 126.7 |
O3—C8—C4 | 118.81 (19) | N1—C10—H10 | 125.0 |
C6—C7—H7 | 119.6 | C11—C10—N1 | 109.9 (2) |
C6—C7—C2 | 120.8 (2) | C11—C10—H10 | 125.0 |
C2—C7—H7 | 119.6 | N6—C23—H23 | 127.1 |
C7—C6—C9 | 120.08 (19) | C22—C23—N6 | 105.8 (3) |
C5—C6—C7 | 118.8 (2) | C22—C23—H23 | 127.1 |
C5—C6—C9 | 121.13 (19) | C13—C14—C15iii | 119.8 (2) |
C7—C2—C1 | 120.02 (19) | C13—C14—H14 | 120.1 |
C3—C2—C7 | 119.79 (19) | C15iii—C14—H14 | 120.1 |
C3—C2—C1 | 120.2 (2) | N5—C22—H22 | 124.9 |
C5—C4—C8 | 121.02 (19) | C23—C22—N5 | 110.2 (2) |
C3—C4—C8 | 119.8 (2) | C23—C22—H22 | 124.9 |
C3—C4—C5 | 119.14 (19) | N2—C11—H11 | 126.8 |
C6—C5—C4 | 121.23 (19) | C10—C11—N2 | 106.4 (3) |
C6—C5—H5A | 119.4 | C10—C11—H11 | 126.8 |
C4—C5—H5A | 119.4 | C19—C20—H20 | 120.3 |
C2—C3—H3 | 119.9 | C19—C20—C21v | 119.4 (3) |
C4—C3—C2 | 120.2 (2) | C21v—C20—H20 | 120.3 |
C4—C3—H3 | 119.9 | C19—C21—C20v | 120.8 (3) |
N3—C18—N4 | 112.5 (2) | C19—C21—H21 | 119.6 |
N3—C18—H18 | 123.8 | C20v—C21—H21 | 119.6 |
Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) −x+1, −y+2, −z+2; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+1, −z+2; (vi) x−1, −y+3/2, z−1/2; (vii) x−1, y, z. |
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