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A novel two-dimensional CoII coordination framework, namely poly[(μ2-biphenyl-4,4′-diyldicarboxylato-κ2O4:O4′){μ2-bis[4-(2-methyl-1H-imidazol-1-yl)phenyl] ether-κ2N3:N3′}cobalt(II)], [Co(C14H8O4)(C20H18N4O)]n, has been prepared and characterized by IR, elemental analysis, thermal analysis and single-crystal X-ray diffraction. The crystal structure reveals that the compound has an achiral two-dimensional layered structure based on opposite-handed helical chains. In addition, it exhibits significant photocatalytic degradation activity for the degradation of methylene blue.
Supporting information
CCDC reference: 1865686
Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).
Poly[(µ
2-biphenyl-4,4'-diyldicarboxylato-
κ2O4:
O4'){µ
2-bis[4-(2-methyl-1
H-imidazol-1-yl)phenyl]
ether-
κ2N3:
N3'}cobalt(II)]
top
Crystal data top
[Co(C14H8O4)(C20H18N4O)] | F(000) = 1300 |
Mr = 629.52 | Dx = 1.511 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.844 (5) Å | Cell parameters from 9179 reflections |
b = 20.558 (13) Å | θ = 2.8–27.4° |
c = 17.168 (12) Å | µ = 0.67 mm−1 |
β = 90.93 (2)° | T = 293 K |
V = 2768 (3) Å3 | Block, red |
Z = 4 | 0.21 × 0.20 × 0.19 mm |
Data collection top
Bruker APEXII CCD diffractometer | 4590 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
φ and ω scans | θmax = 26.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −9→9 |
Tmin = 0.868, Tmax = 0.880 | k = −25→25 |
62557 measured reflections | l = −21→21 |
5441 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0413P)2 + 2.5455P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
5441 reflections | Δρmax = 0.35 e Å−3 |
398 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 | Occ. (<1) |
C1 | 0.2125 (3) | 0.54374 (14) | 0.13562 (16) | 0.0398 (6) | |
C2 | 0.0676 (3) | 0.49695 (13) | 0.12551 (15) | 0.0365 (6) | |
C3 | 0.1010 (3) | 0.43123 (13) | 0.13065 (18) | 0.0433 (7) | |
H3 | 0.213431 | 0.416954 | 0.133507 | 0.052* | |
C4 | −0.0292 (3) | 0.38642 (13) | 0.13164 (18) | 0.0441 (7) | |
H4 | −0.003422 | 0.342398 | 0.136006 | 0.053* | |
C5 | −0.1995 (3) | 0.40599 (12) | 0.12619 (15) | 0.0346 (6) | |
C6 | −0.2321 (3) | 0.47184 (13) | 0.11803 (18) | 0.0437 (7) | |
H6 | −0.344126 | 0.486120 | 0.112451 | 0.052* | |
C7 | −0.1007 (3) | 0.51678 (13) | 0.11803 (18) | 0.0449 (7) | |
H7 | −0.125686 | 0.560812 | 0.112945 | 0.054* | |
C8 | −0.3367 (3) | 0.35800 (12) | 0.13618 (15) | 0.0339 (5) | |
C9 | −0.3283 (3) | 0.29693 (12) | 0.10134 (16) | 0.0379 (6) | |
H9 | −0.240805 | 0.287721 | 0.067130 | 0.046* | |
C10 | −0.4493 (3) | 0.24964 (13) | 0.11718 (15) | 0.0376 (6) | |
H10 | −0.443298 | 0.209422 | 0.092587 | 0.045* | |
C11 | −0.5796 (3) | 0.26164 (12) | 0.16937 (14) | 0.0310 (5) | |
C12 | −0.5899 (3) | 0.32294 (12) | 0.20226 (15) | 0.0362 (6) | |
H12 | −0.677643 | 0.332334 | 0.236271 | 0.043* | |
C13 | −0.4718 (3) | 0.37022 (12) | 0.18523 (16) | 0.0376 (6) | |
H13 | −0.482850 | 0.411342 | 0.207152 | 0.045* | |
C14 | −0.6973 (3) | 0.20765 (12) | 0.19257 (14) | 0.0297 (5) | |
C15 | 0.3919 (3) | 0.52426 (12) | 0.31731 (15) | 0.0356 (6) | |
H15 | 0.273567 | 0.523110 | 0.312879 | 0.043* | |
C16 | 0.4874 (3) | 0.48072 (12) | 0.35587 (15) | 0.0350 (6) | |
H16 | 0.449038 | 0.444493 | 0.382874 | 0.042* | |
C17 | 0.6535 (3) | 0.55580 (11) | 0.30482 (13) | 0.0258 (5) | |
C18 | 0.8057 (3) | 0.59543 (13) | 0.28862 (17) | 0.0391 (6) | |
H18A | 0.905444 | 0.573782 | 0.308797 | 0.059* | 0.5 |
H18B | 0.815745 | 0.601126 | 0.233386 | 0.059* | 0.5 |
H18C | 0.794877 | 0.637164 | 0.313136 | 0.059* | 0.5 |
H18D | 0.771933 | 0.634266 | 0.261416 | 0.059* | 0.5 |
H18E | 0.861632 | 0.606922 | 0.336826 | 0.059* | 0.5 |
H18F | 0.882501 | 0.570884 | 0.257077 | 0.059* | 0.5 |
C19 | 0.7959 (3) | 0.46777 (11) | 0.38447 (14) | 0.0277 (5) | |
C20 | 0.7880 (3) | 0.45446 (12) | 0.46325 (14) | 0.0317 (5) | |
H20 | 0.693444 | 0.467523 | 0.491261 | 0.038* | |
C21 | 0.9188 (3) | 0.42211 (11) | 0.50026 (14) | 0.0315 (5) | |
H21 | 0.912481 | 0.412424 | 0.553050 | 0.038* | |
C22 | 1.0601 (3) | 0.40401 (11) | 0.45851 (14) | 0.0276 (5) | |
C23 | 1.0696 (3) | 0.41630 (12) | 0.37971 (14) | 0.0309 (5) | |
H23 | 1.164835 | 0.403525 | 0.352027 | 0.037* | |
C24 | 0.9348 (3) | 0.44805 (12) | 0.34211 (14) | 0.0312 (5) | |
H24 | 0.938285 | 0.455925 | 0.288822 | 0.037* | |
C25 | 1.3192 (3) | 0.33872 (11) | 0.47805 (13) | 0.0269 (5) | |
C26 | 1.3006 (3) | 0.29374 (12) | 0.41930 (15) | 0.0335 (5) | |
H26 | 1.198461 | 0.290753 | 0.391232 | 0.040* | |
C27 | 1.4352 (3) | 0.25298 (12) | 0.40235 (15) | 0.0346 (6) | |
H27 | 1.424097 | 0.222507 | 0.362556 | 0.042* | |
C28 | 1.5858 (3) | 0.25753 (11) | 0.44441 (13) | 0.0281 (5) | |
C29 | 1.6027 (3) | 0.30194 (12) | 0.50412 (14) | 0.0327 (5) | |
H29 | 1.704021 | 0.304463 | 0.532879 | 0.039* | |
C30 | 1.4685 (3) | 0.34265 (12) | 0.52101 (14) | 0.0324 (5) | |
H30 | 1.478838 | 0.372675 | 0.561324 | 0.039* | |
C31 | 1.7821 (4) | 0.16495 (14) | 0.47592 (16) | 0.0443 (7) | |
H31 | 1.738488 | 0.153352 | 0.524006 | 0.053* | |
C32 | 1.9117 (3) | 0.13672 (13) | 0.43940 (15) | 0.0388 (6) | |
H32 | 1.973652 | 0.101294 | 0.458162 | 0.047* | |
C33 | 1.8258 (3) | 0.21553 (11) | 0.36505 (13) | 0.0275 (5) | |
C34 | 1.8114 (4) | 0.26441 (14) | 0.30243 (17) | 0.0459 (7) | |
H34A | 1.706577 | 0.257954 | 0.273835 | 0.069* | |
H34B | 1.905744 | 0.259876 | 0.267919 | 0.069* | |
H34C | 1.812539 | 0.307219 | 0.324769 | 0.069* | |
Co1 | 0.38825 (4) | 0.63716 (2) | 0.20989 (2) | 0.02535 (10) | |
N1 | 0.4949 (2) | 0.57120 (9) | 0.28504 (11) | 0.0283 (4) | |
N2 | 0.6541 (2) | 0.50020 (9) | 0.34763 (11) | 0.0279 (4) | |
N3 | 1.7257 (2) | 0.21484 (10) | 0.42804 (11) | 0.0302 (4) | |
N4 | 1.9398 (2) | 0.16780 (9) | 0.37013 (11) | 0.0277 (4) | |
O1 | 0.1786 (2) | 0.59997 (9) | 0.16236 (12) | 0.0455 (5) | |
O2 | 0.3594 (3) | 0.52567 (11) | 0.12400 (15) | 0.0620 (6) | |
O3 | −0.8075 (2) | 0.22033 (8) | 0.24528 (10) | 0.0339 (4) | |
O4 | −0.6800 (2) | 0.15338 (8) | 0.16399 (11) | 0.0406 (4) | |
O5 | 1.1910 (2) | 0.37890 (9) | 0.50455 (10) | 0.0386 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0343 (14) | 0.0425 (16) | 0.0426 (15) | −0.0096 (12) | −0.0003 (11) | 0.0032 (12) |
C2 | 0.0324 (13) | 0.0370 (14) | 0.0402 (14) | −0.0078 (11) | 0.0023 (11) | −0.0020 (11) |
C3 | 0.0267 (13) | 0.0417 (15) | 0.0617 (18) | −0.0025 (11) | 0.0038 (12) | −0.0071 (13) |
C4 | 0.0354 (14) | 0.0299 (13) | 0.0673 (19) | −0.0018 (11) | 0.0070 (13) | −0.0058 (13) |
C5 | 0.0329 (13) | 0.0316 (13) | 0.0395 (14) | −0.0032 (10) | 0.0033 (11) | −0.0041 (11) |
C6 | 0.0276 (13) | 0.0377 (15) | 0.0658 (19) | −0.0030 (11) | −0.0024 (12) | 0.0033 (13) |
C7 | 0.0392 (15) | 0.0313 (14) | 0.0642 (19) | −0.0031 (12) | −0.0028 (13) | 0.0024 (13) |
C8 | 0.0291 (12) | 0.0337 (13) | 0.0388 (14) | −0.0032 (10) | −0.0016 (10) | −0.0010 (11) |
C9 | 0.0343 (14) | 0.0362 (14) | 0.0436 (15) | −0.0046 (11) | 0.0097 (11) | −0.0077 (11) |
C10 | 0.0378 (14) | 0.0340 (14) | 0.0412 (14) | −0.0058 (11) | 0.0065 (11) | −0.0093 (11) |
C11 | 0.0279 (12) | 0.0315 (13) | 0.0334 (13) | −0.0025 (10) | −0.0015 (10) | 0.0008 (10) |
C12 | 0.0307 (13) | 0.0353 (14) | 0.0428 (15) | 0.0005 (11) | 0.0077 (11) | −0.0021 (11) |
C13 | 0.0354 (14) | 0.0294 (13) | 0.0481 (15) | 0.0010 (11) | 0.0042 (11) | −0.0080 (11) |
C14 | 0.0259 (12) | 0.0333 (13) | 0.0298 (12) | −0.0056 (10) | −0.0038 (10) | 0.0032 (10) |
C15 | 0.0215 (12) | 0.0386 (14) | 0.0467 (15) | 0.0006 (10) | 0.0022 (10) | 0.0106 (12) |
C16 | 0.0262 (12) | 0.0332 (13) | 0.0456 (15) | −0.0021 (10) | 0.0039 (11) | 0.0114 (11) |
C17 | 0.0240 (11) | 0.0256 (12) | 0.0277 (12) | 0.0030 (9) | 0.0015 (9) | 0.0005 (9) |
C18 | 0.0289 (13) | 0.0369 (14) | 0.0514 (16) | −0.0027 (11) | −0.0007 (11) | 0.0114 (12) |
C19 | 0.0240 (11) | 0.0248 (12) | 0.0344 (13) | 0.0038 (9) | −0.0010 (9) | 0.0047 (9) |
C20 | 0.0248 (12) | 0.0349 (13) | 0.0356 (13) | 0.0061 (10) | 0.0075 (10) | 0.0032 (10) |
C21 | 0.0330 (13) | 0.0319 (13) | 0.0296 (13) | 0.0058 (10) | 0.0050 (10) | 0.0053 (10) |
C22 | 0.0253 (11) | 0.0236 (11) | 0.0338 (13) | 0.0060 (9) | −0.0023 (9) | 0.0016 (9) |
C23 | 0.0246 (12) | 0.0342 (13) | 0.0341 (13) | 0.0091 (10) | 0.0058 (10) | 0.0010 (10) |
C24 | 0.0323 (13) | 0.0330 (13) | 0.0283 (12) | 0.0042 (10) | 0.0025 (10) | 0.0055 (10) |
C25 | 0.0252 (11) | 0.0280 (12) | 0.0277 (12) | 0.0075 (9) | 0.0029 (9) | 0.0047 (9) |
C26 | 0.0254 (12) | 0.0368 (14) | 0.0381 (14) | 0.0045 (10) | −0.0060 (10) | −0.0040 (11) |
C27 | 0.0340 (13) | 0.0344 (13) | 0.0352 (13) | 0.0050 (11) | −0.0053 (10) | −0.0116 (11) |
C28 | 0.0252 (11) | 0.0300 (12) | 0.0290 (12) | 0.0067 (9) | 0.0024 (9) | −0.0010 (10) |
C29 | 0.0253 (12) | 0.0396 (14) | 0.0331 (13) | 0.0047 (10) | −0.0049 (10) | −0.0053 (11) |
C30 | 0.0330 (13) | 0.0328 (13) | 0.0313 (13) | 0.0046 (10) | −0.0015 (10) | −0.0091 (10) |
C31 | 0.0497 (17) | 0.0495 (16) | 0.0340 (14) | 0.0161 (13) | 0.0098 (12) | 0.0099 (12) |
C32 | 0.0427 (15) | 0.0376 (14) | 0.0362 (14) | 0.0155 (12) | 0.0039 (11) | 0.0066 (11) |
C33 | 0.0254 (11) | 0.0286 (12) | 0.0285 (12) | 0.0023 (9) | −0.0020 (9) | −0.0029 (9) |
C34 | 0.0455 (16) | 0.0460 (16) | 0.0467 (16) | 0.0153 (13) | 0.0109 (13) | 0.0131 (13) |
Co1 | 0.02015 (16) | 0.02281 (17) | 0.03310 (18) | −0.00055 (12) | 0.00090 (12) | 0.00363 (13) |
N1 | 0.0229 (10) | 0.0266 (10) | 0.0353 (11) | 0.0032 (8) | 0.0017 (8) | 0.0050 (8) |
N2 | 0.0224 (9) | 0.0273 (10) | 0.0341 (11) | 0.0024 (8) | 0.0017 (8) | 0.0061 (8) |
N3 | 0.0282 (10) | 0.0325 (11) | 0.0300 (11) | 0.0098 (8) | 0.0018 (8) | −0.0016 (8) |
N4 | 0.0251 (10) | 0.0267 (10) | 0.0313 (10) | 0.0043 (8) | 0.0009 (8) | −0.0032 (8) |
O1 | 0.0419 (11) | 0.0362 (11) | 0.0583 (12) | −0.0104 (8) | −0.0090 (9) | −0.0046 (9) |
O2 | 0.0323 (11) | 0.0580 (13) | 0.0960 (18) | −0.0087 (10) | 0.0064 (11) | 0.0024 (12) |
O3 | 0.0320 (9) | 0.0309 (9) | 0.0391 (10) | −0.0038 (7) | 0.0079 (8) | 0.0009 (7) |
O4 | 0.0391 (10) | 0.0329 (10) | 0.0500 (11) | −0.0087 (8) | 0.0068 (8) | −0.0061 (8) |
O5 | 0.0367 (10) | 0.0485 (11) | 0.0307 (9) | 0.0233 (8) | −0.0024 (7) | −0.0030 (8) |
Geometric parameters (Å, º) top
C1—O2 | 1.231 (3) | C18—H18F | 0.9600 |
C1—O1 | 1.273 (3) | C19—C24 | 1.381 (3) |
C1—C2 | 1.496 (4) | C19—C20 | 1.382 (3) |
C2—C3 | 1.379 (4) | C19—N2 | 1.435 (3) |
C2—C7 | 1.386 (4) | C20—C21 | 1.370 (3) |
C3—C4 | 1.376 (4) | C20—H20 | 0.9300 |
C3—H3 | 0.9300 | C21—C22 | 1.381 (3) |
C4—C5 | 1.397 (4) | C21—H21 | 0.9300 |
C4—H4 | 0.9300 | C22—C23 | 1.379 (3) |
C5—C6 | 1.384 (4) | C22—O5 | 1.385 (3) |
C5—C8 | 1.472 (3) | C23—C24 | 1.392 (3) |
C6—C7 | 1.384 (4) | C23—H23 | 0.9300 |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—H7 | 0.9300 | C25—C26 | 1.374 (3) |
C8—C13 | 1.387 (4) | C25—C30 | 1.376 (3) |
C8—C9 | 1.393 (4) | C25—O5 | 1.384 (3) |
C9—C10 | 1.389 (4) | C26—C27 | 1.383 (3) |
C9—H9 | 0.9300 | C26—H26 | 0.9300 |
C10—C11 | 1.392 (4) | C27—C28 | 1.378 (3) |
C10—H10 | 0.9300 | C27—H27 | 0.9300 |
C11—C12 | 1.384 (4) | C28—C29 | 1.377 (3) |
C11—C14 | 1.502 (3) | C28—N3 | 1.436 (3) |
C12—C13 | 1.378 (4) | C29—C30 | 1.380 (3) |
C12—H12 | 0.9300 | C29—H29 | 0.9300 |
C13—H13 | 0.9300 | C30—H30 | 0.9300 |
C14—O4 | 1.227 (3) | C31—C32 | 1.336 (4) |
C14—O3 | 1.288 (3) | C31—N3 | 1.383 (3) |
C15—C16 | 1.336 (3) | C31—H31 | 0.9300 |
C15—N1 | 1.381 (3) | C32—N4 | 1.371 (3) |
C15—H15 | 0.9300 | C32—H32 | 0.9300 |
C16—N2 | 1.377 (3) | C33—N4 | 1.330 (3) |
C16—H16 | 0.9300 | C33—N3 | 1.347 (3) |
C17—N1 | 1.323 (3) | C33—C34 | 1.475 (4) |
C17—N2 | 1.359 (3) | C34—H34A | 0.9600 |
C17—C18 | 1.476 (3) | C34—H34B | 0.9600 |
C18—H18A | 0.9600 | C34—H34C | 0.9600 |
C18—H18B | 0.9600 | Co1—O1 | 1.977 (2) |
C18—H18C | 0.9600 | Co1—O3i | 1.9831 (19) |
C18—H18D | 0.9600 | Co1—N4ii | 2.040 (2) |
C18—H18E | 0.9600 | Co1—N1 | 2.042 (2) |
| | | |
O2—C1—O1 | 122.3 (2) | C20—C21—C22 | 119.4 (2) |
O2—C1—C2 | 119.9 (3) | C20—C21—H21 | 120.3 |
O1—C1—C2 | 117.6 (2) | C22—C21—H21 | 120.3 |
C3—C2—C7 | 118.3 (2) | C23—C22—C21 | 121.1 (2) |
C3—C2—C1 | 118.7 (2) | C23—C22—O5 | 125.2 (2) |
C7—C2—C1 | 122.8 (2) | C21—C22—O5 | 113.4 (2) |
C4—C3—C2 | 121.1 (3) | C22—C23—C24 | 119.2 (2) |
C4—C3—H3 | 119.4 | C22—C23—H23 | 120.4 |
C2—C3—H3 | 119.4 | C24—C23—H23 | 120.4 |
C3—C4—C5 | 121.0 (3) | C19—C24—C23 | 119.6 (2) |
C3—C4—H4 | 119.5 | C19—C24—H24 | 120.2 |
C5—C4—H4 | 119.5 | C23—C24—H24 | 120.2 |
C6—C5—C4 | 117.6 (2) | C26—C25—C30 | 120.8 (2) |
C6—C5—C8 | 122.2 (2) | C26—C25—O5 | 125.0 (2) |
C4—C5—C8 | 119.9 (2) | C30—C25—O5 | 113.9 (2) |
C7—C6—C5 | 121.1 (3) | C25—C26—C27 | 119.3 (2) |
C7—C6—H6 | 119.4 | C25—C26—H26 | 120.3 |
C5—C6—H6 | 119.4 | C27—C26—H26 | 120.3 |
C6—C7—C2 | 120.8 (3) | C28—C27—C26 | 120.0 (2) |
C6—C7—H7 | 119.6 | C28—C27—H27 | 120.0 |
C2—C7—H7 | 119.6 | C26—C27—H27 | 120.0 |
C13—C8—C9 | 117.8 (2) | C29—C28—C27 | 120.4 (2) |
C13—C8—C5 | 121.1 (2) | C29—C28—N3 | 119.1 (2) |
C9—C8—C5 | 121.0 (2) | C27—C28—N3 | 120.5 (2) |
C10—C9—C8 | 120.6 (2) | C28—C29—C30 | 119.6 (2) |
C10—C9—H9 | 119.7 | C28—C29—H29 | 120.2 |
C8—C9—H9 | 119.7 | C30—C29—H29 | 120.2 |
C9—C10—C11 | 120.9 (2) | C25—C30—C29 | 119.8 (2) |
C9—C10—H10 | 119.6 | C25—C30—H30 | 120.1 |
C11—C10—H10 | 119.6 | C29—C30—H30 | 120.1 |
C12—C11—C10 | 118.2 (2) | C32—C31—N3 | 106.4 (2) |
C12—C11—C14 | 121.6 (2) | C32—C31—H31 | 126.8 |
C10—C11—C14 | 120.0 (2) | N3—C31—H31 | 126.8 |
C13—C12—C11 | 120.8 (2) | C31—C32—N4 | 109.8 (2) |
C13—C12—H12 | 119.6 | C31—C32—H32 | 125.1 |
C11—C12—H12 | 119.6 | N4—C32—H32 | 125.1 |
C12—C13—C8 | 121.6 (2) | N4—C33—N3 | 109.9 (2) |
C12—C13—H13 | 119.2 | N4—C33—C34 | 126.4 (2) |
C8—C13—H13 | 119.2 | N3—C33—C34 | 123.6 (2) |
O4—C14—O3 | 123.0 (2) | C33—C34—H34A | 109.5 |
O4—C14—C11 | 119.6 (2) | C33—C34—H34B | 109.5 |
O3—C14—C11 | 117.3 (2) | H34A—C34—H34B | 109.5 |
C16—C15—N1 | 109.9 (2) | C33—C34—H34C | 109.5 |
C16—C15—H15 | 125.1 | H34A—C34—H34C | 109.5 |
N1—C15—H15 | 125.1 | H34B—C34—H34C | 109.5 |
C15—C16—N2 | 106.3 (2) | O1—Co1—O3i | 102.99 (8) |
C15—C16—H16 | 126.9 | O1—Co1—N4ii | 113.31 (9) |
N2—C16—H16 | 126.9 | O3i—Co1—N4ii | 102.36 (8) |
N1—C17—N2 | 109.59 (19) | O1—Co1—N1 | 109.47 (9) |
N1—C17—C18 | 125.4 (2) | O3i—Co1—N1 | 117.23 (9) |
N2—C17—C18 | 124.8 (2) | N4ii—Co1—N1 | 111.23 (9) |
C17—C18—H18A | 109.5 | C17—N1—C15 | 106.49 (19) |
C17—C18—H18B | 109.5 | C17—N1—Co1 | 134.04 (16) |
H18A—C18—H18B | 109.5 | C15—N1—Co1 | 118.78 (16) |
C17—C18—H18C | 109.5 | C17—N2—C16 | 107.76 (19) |
H18A—C18—H18C | 109.5 | C17—N2—C19 | 128.70 (19) |
H18B—C18—H18C | 109.5 | C16—N2—C19 | 123.38 (19) |
H18D—C18—H18E | 109.5 | C33—N3—C31 | 107.5 (2) |
H18D—C18—H18F | 109.5 | C33—N3—C28 | 127.4 (2) |
H18E—C18—H18F | 109.5 | C31—N3—C28 | 125.1 (2) |
C24—C19—C20 | 120.4 (2) | C33—N4—C32 | 106.45 (19) |
C24—C19—N2 | 121.1 (2) | C33—N4—Co1iii | 129.43 (16) |
C20—C19—N2 | 118.5 (2) | C32—N4—Co1iii | 123.89 (16) |
C21—C20—C19 | 120.3 (2) | C1—O1—Co1 | 108.85 (17) |
C21—C20—H20 | 119.8 | C14—O3—Co1iv | 108.69 (15) |
C19—C20—H20 | 119.8 | C25—O5—C22 | 124.78 (19) |
| | | |
O2—C1—C2—C3 | 22.7 (4) | C26—C27—C28—N3 | 179.1 (2) |
O1—C1—C2—C3 | −151.7 (3) | C27—C28—C29—C30 | −0.9 (4) |
O2—C1—C2—C7 | −163.2 (3) | N3—C28—C29—C30 | −179.2 (2) |
O1—C1—C2—C7 | 22.4 (4) | C26—C25—C30—C29 | 1.3 (4) |
C7—C2—C3—C4 | −2.7 (4) | O5—C25—C30—C29 | 175.6 (2) |
C1—C2—C3—C4 | 171.8 (3) | C28—C29—C30—C25 | −0.2 (4) |
C2—C3—C4—C5 | 1.0 (5) | N3—C31—C32—N4 | 0.6 (3) |
C3—C4—C5—C6 | 1.4 (4) | N2—C17—N1—C15 | 0.8 (3) |
C3—C4—C5—C8 | −173.1 (3) | C18—C17—N1—C15 | −174.6 (2) |
C4—C5—C6—C7 | −2.2 (4) | N2—C17—N1—Co1 | −169.21 (16) |
C8—C5—C6—C7 | 172.2 (3) | C18—C17—N1—Co1 | 15.4 (4) |
C5—C6—C7—C2 | 0.6 (5) | C16—C15—N1—C17 | −0.3 (3) |
C3—C2—C7—C6 | 1.9 (4) | C16—C15—N1—Co1 | 171.51 (18) |
C1—C2—C7—C6 | −172.3 (3) | N1—C17—N2—C16 | −1.0 (3) |
C6—C5—C8—C13 | −42.7 (4) | C18—C17—N2—C16 | 174.4 (2) |
C4—C5—C8—C13 | 131.6 (3) | N1—C17—N2—C19 | −176.5 (2) |
C6—C5—C8—C9 | 142.3 (3) | C18—C17—N2—C19 | −1.0 (4) |
C4—C5—C8—C9 | −43.4 (4) | C15—C16—N2—C17 | 0.8 (3) |
C13—C8—C9—C10 | −1.7 (4) | C15—C16—N2—C19 | 176.5 (2) |
C5—C8—C9—C10 | 173.6 (2) | C24—C19—N2—C17 | −56.9 (3) |
C8—C9—C10—C11 | −1.3 (4) | C20—C19—N2—C17 | 125.4 (3) |
C9—C10—C11—C12 | 3.0 (4) | C24—C19—N2—C16 | 128.3 (3) |
C9—C10—C11—C14 | −173.1 (2) | C20—C19—N2—C16 | −49.4 (3) |
C10—C11—C12—C13 | −1.6 (4) | N4—C33—N3—C31 | 1.3 (3) |
C14—C11—C12—C13 | 174.4 (2) | C34—C33—N3—C31 | −176.5 (3) |
C11—C12—C13—C8 | −1.4 (4) | N4—C33—N3—C28 | −179.0 (2) |
C9—C8—C13—C12 | 3.0 (4) | C34—C33—N3—C28 | 3.2 (4) |
C5—C8—C13—C12 | −172.2 (2) | C32—C31—N3—C33 | −1.1 (3) |
C12—C11—C14—O4 | −177.4 (2) | C32—C31—N3—C28 | 179.2 (2) |
C10—C11—C14—O4 | −1.5 (4) | C29—C28—N3—C33 | −110.7 (3) |
C12—C11—C14—O3 | −0.9 (3) | C27—C28—N3—C33 | 71.0 (3) |
C10—C11—C14—O3 | 175.1 (2) | C29—C28—N3—C31 | 69.0 (3) |
N1—C15—C16—N2 | −0.3 (3) | C27—C28—N3—C31 | −109.3 (3) |
C24—C19—C20—C21 | 0.7 (4) | N3—C33—N4—C32 | −0.9 (3) |
N2—C19—C20—C21 | 178.4 (2) | C34—C33—N4—C32 | 176.8 (3) |
C19—C20—C21—C22 | 1.2 (4) | N3—C33—N4—Co1iii | 173.54 (15) |
C20—C21—C22—C23 | −1.9 (4) | C34—C33—N4—Co1iii | −8.7 (4) |
C20—C21—C22—O5 | 172.6 (2) | C31—C32—N4—C33 | 0.2 (3) |
C21—C22—C23—C24 | 0.6 (4) | C31—C32—N4—Co1iii | −174.66 (19) |
O5—C22—C23—C24 | −173.2 (2) | O2—C1—O1—Co1 | −17.4 (3) |
C20—C19—C24—C23 | −1.9 (4) | C2—C1—O1—Co1 | 156.87 (19) |
N2—C19—C24—C23 | −179.5 (2) | O4—C14—O3—Co1iv | 15.6 (3) |
C22—C23—C24—C19 | 1.3 (4) | C11—C14—O3—Co1iv | −160.79 (16) |
C30—C25—C26—C27 | −1.4 (4) | C26—C25—O5—C22 | −33.0 (4) |
O5—C25—C26—C27 | −175.0 (2) | C30—C25—O5—C22 | 153.0 (2) |
C25—C26—C27—C28 | 0.3 (4) | C23—C22—O5—C25 | −27.9 (4) |
C26—C27—C28—C29 | 0.9 (4) | C21—C22—O5—C25 | 157.9 (2) |
Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+5/2, y−1/2, −z+1/2; (iv) −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 |
C21—H21···O4v | 0.93 | 2.46 | 3.314 (3) | 154 |
C29—H29···O4vi | 0.93 | 2.57 | 3.336 (4) | 141 |
C32—H32···O2iii | 0.93 | 2.49 | 3.112 (4) | 125 |
C34—H34B···O3vii | 0.96 | 2.43 | 3.289 (4) | 149 |
C21—H21···O4v | 0.93 | 2.46 | 3.314 (3) | 154 |
C29—H29···O4vi | 0.93 | 2.57 | 3.336 (4) | 141 |
C32—H32···O2iii | 0.93 | 2.49 | 3.112 (4) | 125 |
C34—H34B···O3vii | 0.96 | 2.43 | 3.289 (4) | 149 |
Symmetry codes: (iii) −x+5/2, y−1/2, −z+1/2; (v) x+3/2, −y+1/2, z+1/2; (vi) x+5/2, −y+1/2, z+1/2; (vii) x+3, y, z. |
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