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metal-organic compounds
In the title mononuclear complex, [Cu(C14H9O3)2(CH4O)(H2O)]·2CH3OH, the CuII atom has an elongated octahedral coordination environment, defined by two hydroxyl and two carboxylate O atoms from two bidentate 9-hydroxyfluorene-9-carboxylate ligands, and one water and one methanol molecule in cis positions. A supramolecular chain structure is constructed via hydrogen-bonding interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026716/ob6425sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026716/ob6425Isup2.hkl |
CCDC reference: 255469
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.057
- wR factor = 0.154
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - O7 .. 11.54 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.26 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.75 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C H4 O
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Aquabis(9-hydroxyfluorene-9-carboxylato)(methanol)copper(II) methanol disolvate top
Crystal data top
[Cu(C14H9O3)2(CH4O)(H2O)]·2CH4O | F(000) = 1308 |
Mr = 628.12 | Dx = 1.397 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 19670 reflections |
a = 13.592 (3) Å | θ = 3.1–27.5° |
b = 7.5178 (15) Å | µ = 0.79 mm−1 |
c = 29.233 (6) Å | T = 293 K |
β = 90.69 (3)° | Prism, blue |
V = 2986.9 (11) Å3 | 0.39 × 0.25 × 0.18 mm |
Z = 4 |
Data collection top
Rigaku RAXIS-RAPID diffractometer | 6772 independent reflections |
Radiation source: fine-focus sealed tube | 5332 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −9→9 |
Tmin = 0.749, Tmax = 0.871 | l = −37→37 |
26886 measured reflections |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0755P)2 + 2.4818P] where P = (Fo2 + 2Fc2)/3 |
6772 reflections | (Δ/σ)max = 0.001 |
397 parameters | Δρmax = 0.86 e Å−3 |
5 restraints | Δρmin = −0.38 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.33997 (2) | 0.36708 (4) | 0.294648 (12) | 0.04010 (13) | |
O1 | 0.30838 (15) | 0.6092 (2) | 0.31333 (7) | 0.0425 (4) | |
O2 | 0.26438 (19) | 0.8120 (3) | 0.36392 (9) | 0.0603 (6) | |
O3 | 0.24581 (17) | 0.3421 (3) | 0.36143 (8) | 0.0501 (5) | |
O4 | 0.38224 (14) | 0.1320 (2) | 0.27548 (7) | 0.0447 (5) | |
O5 | 0.49370 (15) | −0.0818 (3) | 0.28452 (8) | 0.0507 (5) | |
O6 | 0.46237 (14) | 0.3505 (2) | 0.33194 (8) | 0.0440 (5) | |
O7 | 0.4432 (2) | 0.5437 (4) | 0.23990 (9) | 0.0683 (7) | |
O8 | 0.1881 (4) | 1.0749 (4) | 0.41502 (13) | 0.1229 (16) | |
O9 | 0.5614 (2) | −0.3602 (3) | 0.34001 (16) | 0.0978 (12) | |
O1W | 0.22488 (17) | 0.3526 (3) | 0.25478 (8) | 0.0505 (5) | |
C1 | 0.2697 (2) | 0.6564 (4) | 0.35124 (10) | 0.0412 (6) | |
C2 | 0.2229 (2) | 0.5102 (4) | 0.38122 (11) | 0.0442 (7) | |
C3 | 0.1122 (2) | 0.5497 (4) | 0.38305 (11) | 0.0482 (7) | |
C4 | 0.0438 (3) | 0.5499 (5) | 0.34786 (15) | 0.0658 (9) | |
C5 | −0.0525 (3) | 0.6008 (6) | 0.3577 (2) | 0.0854 (14) | |
C6 | −0.0772 (3) | 0.6507 (7) | 0.4015 (2) | 0.0986 (18) | |
C7 | −0.0095 (4) | 0.6501 (6) | 0.43671 (19) | 0.0855 (14) | |
C8 | 0.0876 (3) | 0.5993 (4) | 0.42778 (13) | 0.0590 (9) | |
C9 | 0.1746 (3) | 0.5843 (4) | 0.45750 (12) | 0.0595 (9) | |
C10 | 0.1880 (5) | 0.6107 (6) | 0.50454 (15) | 0.0877 (15) | |
C11 | 0.2780 (6) | 0.5783 (7) | 0.52393 (17) | 0.107 (2) | |
C12 | 0.3557 (5) | 0.5206 (8) | 0.49762 (19) | 0.0998 (17) | |
C13 | 0.3449 (3) | 0.4971 (6) | 0.45089 (15) | 0.0743 (11) | |
C14 | 0.2540 (3) | 0.5282 (4) | 0.43105 (11) | 0.0517 (7) | |
C15 | 0.46198 (19) | 0.0683 (4) | 0.29290 (10) | 0.0389 (6) | |
C16 | 0.5199 (2) | 0.1905 (4) | 0.32610 (10) | 0.0404 (6) | |
C17 | 0.6235 (2) | 0.2261 (4) | 0.30864 (11) | 0.0437 (6) | |
C18 | 0.6516 (2) | 0.3083 (4) | 0.26848 (12) | 0.0540 (8) | |
C19 | 0.7516 (3) | 0.3278 (5) | 0.26036 (15) | 0.0666 (10) | |
C20 | 0.8211 (3) | 0.2676 (6) | 0.29128 (16) | 0.0738 (12) | |
C21 | 0.7936 (3) | 0.1855 (6) | 0.33135 (16) | 0.0691 (11) | |
C22 | 0.6933 (2) | 0.1656 (4) | 0.34054 (12) | 0.0505 (7) | |
C23 | 0.6417 (3) | 0.0875 (4) | 0.37984 (12) | 0.0530 (8) | |
C24 | 0.6770 (3) | 0.0088 (6) | 0.41966 (15) | 0.0764 (12) | |
C25 | 0.6098 (5) | −0.0624 (7) | 0.45021 (16) | 0.0909 (15) | |
C26 | 0.5102 (4) | −0.0556 (6) | 0.44143 (14) | 0.0812 (13) | |
C27 | 0.4737 (3) | 0.0271 (5) | 0.40202 (12) | 0.0631 (9) | |
C28 | 0.5404 (2) | 0.0983 (4) | 0.37152 (11) | 0.0464 (7) | |
C29 | 0.4253 (4) | 0.5391 (7) | 0.19310 (15) | 0.0831 (12) | |
C30 | 0.1517 (8) | 1.0766 (8) | 0.4546 (3) | 0.191 (5) | |
C31 | 0.6559 (4) | −0.3570 (6) | 0.3522 (2) | 0.1076 (19) | |
H1W1 | 0.198 (3) | 0.448 (3) | 0.2459 (11) | 0.076* | |
H1W2 | 0.223 (3) | 0.274 (3) | 0.2342 (9) | 0.076* | |
H4 | 0.0613 | 0.5172 | 0.3184 | 0.079* | |
H5 | −0.1002 | 0.6011 | 0.3346 | 0.103* | |
H6 | −0.1415 | 0.6856 | 0.4073 | 0.118* | |
H7 | −0.0277 | 0.6830 | 0.4661 | 0.103* | |
H10 | 0.1362 | 0.6499 | 0.5224 | 0.105* | |
H11 | 0.2872 | 0.5952 | 0.5552 | 0.128* | |
H12 | 0.4162 | 0.4973 | 0.5116 | 0.120* | |
H13 | 0.3978 | 0.4611 | 0.4333 | 0.089* | |
H18 | 0.6049 | 0.3494 | 0.2475 | 0.065* | |
H19 | 0.7719 | 0.3825 | 0.2335 | 0.080* | |
H20 | 0.8875 | 0.2826 | 0.2851 | 0.089* | |
H21 | 0.8410 | 0.1439 | 0.3519 | 0.083* | |
H24 | 0.7442 | 0.0036 | 0.4258 | 0.092* | |
H25 | 0.6327 | −0.1154 | 0.4770 | 0.109* | |
H26 | 0.4668 | −0.1066 | 0.4620 | 0.097* | |
H27 | 0.4064 | 0.0342 | 0.3963 | 0.076* | |
H29A | 0.3679 | 0.6087 | 0.1860 | 0.125* | |
H29B | 0.4147 | 0.4184 | 0.1836 | 0.125* | |
H29C | 0.4809 | 0.5871 | 0.1774 | 0.125* | |
H30A | 0.1982 | 1.0274 | 0.4761 | 0.287* | |
H30B | 0.0925 | 1.0068 | 0.4547 | 0.287* | |
H30C | 0.1367 | 1.1968 | 0.4631 | 0.287* | |
H31A | 0.6888 | −0.2638 | 0.3360 | 0.161* | |
H31B | 0.6857 | −0.4692 | 0.3451 | 0.161* | |
H31C | 0.6616 | −0.3356 | 0.3845 | 0.161* | |
H32 | 0.230 (3) | 0.259 (4) | 0.3795 (11) | 0.075* | |
H33 | 0.497 (2) | 0.443 (3) | 0.3345 (13) | 0.066* | |
H34 | 0.4384 | 0.6463 | 0.2491 | 0.102* | |
H35 | 0.2113 | 0.9763 | 0.4098 | 0.184* | |
H36 | 0.5521 | −0.2917 | 0.3186 | 0.147* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03667 (19) | 0.03185 (19) | 0.0519 (2) | 0.00543 (13) | 0.00491 (14) | −0.00101 (15) |
O1 | 0.0465 (11) | 0.0323 (9) | 0.0490 (11) | 0.0025 (8) | 0.0110 (9) | 0.0033 (8) |
O2 | 0.0758 (16) | 0.0328 (10) | 0.0729 (15) | −0.0033 (10) | 0.0265 (13) | −0.0056 (10) |
O3 | 0.0610 (13) | 0.0309 (10) | 0.0590 (13) | −0.0009 (9) | 0.0212 (11) | −0.0002 (9) |
O4 | 0.0392 (10) | 0.0352 (10) | 0.0598 (12) | 0.0044 (8) | −0.0035 (9) | −0.0035 (9) |
O5 | 0.0462 (11) | 0.0338 (10) | 0.0720 (14) | 0.0076 (9) | −0.0023 (10) | −0.0077 (10) |
O6 | 0.0391 (10) | 0.0297 (9) | 0.0633 (13) | 0.0029 (8) | 0.0038 (9) | −0.0069 (9) |
O7 | 0.0686 (16) | 0.0606 (15) | 0.0761 (17) | 0.0058 (13) | 0.0135 (13) | 0.0044 (13) |
O8 | 0.221 (5) | 0.0401 (14) | 0.110 (3) | 0.006 (2) | 0.097 (3) | 0.0012 (16) |
O9 | 0.080 (2) | 0.0398 (14) | 0.172 (4) | 0.0002 (13) | −0.039 (2) | 0.0067 (17) |
O1W | 0.0514 (12) | 0.0364 (11) | 0.0634 (14) | 0.0120 (9) | −0.0090 (10) | −0.0080 (10) |
C1 | 0.0393 (14) | 0.0334 (13) | 0.0511 (16) | −0.0005 (11) | 0.0077 (12) | −0.0010 (12) |
C2 | 0.0476 (16) | 0.0313 (13) | 0.0539 (17) | −0.0004 (12) | 0.0134 (13) | −0.0023 (12) |
C3 | 0.0478 (16) | 0.0351 (14) | 0.0621 (19) | −0.0040 (12) | 0.0134 (14) | −0.0008 (14) |
C4 | 0.055 (2) | 0.056 (2) | 0.087 (3) | −0.0087 (16) | 0.0066 (18) | −0.0019 (19) |
C5 | 0.050 (2) | 0.069 (3) | 0.137 (4) | −0.0045 (19) | −0.004 (2) | 0.008 (3) |
C6 | 0.050 (2) | 0.084 (3) | 0.163 (6) | 0.006 (2) | 0.034 (3) | 0.000 (3) |
C7 | 0.074 (3) | 0.075 (3) | 0.108 (4) | 0.002 (2) | 0.050 (3) | −0.009 (3) |
C8 | 0.062 (2) | 0.0419 (16) | 0.073 (2) | −0.0016 (15) | 0.0304 (17) | 0.0016 (16) |
C9 | 0.086 (3) | 0.0406 (16) | 0.0523 (18) | −0.0099 (17) | 0.0203 (18) | −0.0016 (14) |
C10 | 0.148 (5) | 0.057 (2) | 0.059 (2) | −0.004 (3) | 0.030 (3) | −0.0030 (19) |
C11 | 0.185 (7) | 0.075 (3) | 0.059 (3) | −0.026 (4) | −0.020 (4) | 0.008 (2) |
C12 | 0.122 (4) | 0.090 (4) | 0.086 (3) | −0.017 (3) | −0.035 (3) | 0.014 (3) |
C13 | 0.076 (3) | 0.072 (3) | 0.074 (3) | −0.005 (2) | −0.012 (2) | 0.011 (2) |
C14 | 0.065 (2) | 0.0370 (15) | 0.0535 (18) | −0.0058 (14) | 0.0080 (15) | 0.0030 (13) |
C15 | 0.0330 (13) | 0.0331 (13) | 0.0508 (16) | −0.0008 (10) | 0.0075 (11) | −0.0001 (12) |
C16 | 0.0348 (13) | 0.0329 (13) | 0.0536 (16) | 0.0033 (10) | 0.0057 (12) | −0.0004 (12) |
C17 | 0.0356 (14) | 0.0315 (13) | 0.0642 (18) | 0.0007 (11) | 0.0061 (13) | −0.0049 (13) |
C18 | 0.0500 (17) | 0.0444 (16) | 0.068 (2) | 0.0022 (14) | 0.0127 (15) | 0.0034 (15) |
C19 | 0.058 (2) | 0.0525 (19) | 0.090 (3) | −0.0034 (16) | 0.028 (2) | 0.0016 (19) |
C20 | 0.0435 (19) | 0.065 (2) | 0.113 (3) | −0.0071 (17) | 0.021 (2) | −0.012 (2) |
C21 | 0.0408 (17) | 0.067 (2) | 0.099 (3) | 0.0049 (16) | −0.0058 (19) | −0.013 (2) |
C22 | 0.0400 (15) | 0.0402 (15) | 0.071 (2) | 0.0036 (12) | −0.0010 (14) | −0.0083 (15) |
C23 | 0.0580 (19) | 0.0413 (15) | 0.0595 (19) | 0.0066 (14) | −0.0090 (15) | −0.0048 (15) |
C24 | 0.083 (3) | 0.074 (3) | 0.072 (3) | 0.016 (2) | −0.019 (2) | −0.002 (2) |
C25 | 0.139 (5) | 0.074 (3) | 0.060 (2) | 0.016 (3) | −0.008 (3) | 0.011 (2) |
C26 | 0.118 (4) | 0.068 (3) | 0.059 (2) | −0.006 (3) | 0.018 (2) | 0.009 (2) |
C27 | 0.076 (2) | 0.056 (2) | 0.058 (2) | −0.0057 (18) | 0.0140 (18) | −0.0012 (17) |
C28 | 0.0531 (17) | 0.0327 (14) | 0.0536 (17) | 0.0000 (12) | 0.0050 (14) | −0.0030 (12) |
C29 | 0.088 (3) | 0.084 (3) | 0.077 (3) | 0.002 (2) | 0.007 (2) | 0.004 (2) |
C30 | 0.365 (13) | 0.064 (3) | 0.148 (6) | −0.023 (5) | 0.139 (8) | −0.012 (4) |
C31 | 0.120 (5) | 0.061 (3) | 0.142 (5) | −0.005 (3) | −0.028 (4) | −0.016 (3) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.950 (2) | C11—C12 | 1.384 (9) |
Cu1—O3 | 2.355 (2) | C11—H11 | 0.9300 |
Cu1—O4 | 1.943 (2) | C12—C13 | 1.384 (7) |
Cu1—O6 | 1.982 (2) | C12—H12 | 0.9300 |
Cu1—O7 | 2.519 (2) | C13—C14 | 1.378 (5) |
Cu1—O1W | 1.943 (2) | C13—H13 | 0.9300 |
O1—C1 | 1.283 (4) | C15—C16 | 1.545 (4) |
O2—C1 | 1.229 (3) | C16—C28 | 1.521 (4) |
O4—C15 | 1.284 (3) | C16—C17 | 1.527 (4) |
O5—C15 | 1.233 (3) | C17—C18 | 1.384 (5) |
O3—C2 | 1.426 (3) | C17—C22 | 1.398 (4) |
O3—H32 | 0.85 (3) | C18—C19 | 1.391 (5) |
O6—C16 | 1.446 (3) | C18—H18 | 0.9300 |
O6—H33 | 0.84 (3) | C19—C20 | 1.376 (6) |
O7—C29 | 1.387 (5) | C19—H19 | 0.9300 |
O7—H34 | 0.8200 | C20—C21 | 1.380 (6) |
O8—C30 | 1.264 (7) | C20—H20 | 0.9300 |
O8—H35 | 0.8200 | C21—C22 | 1.401 (5) |
O9—C31 | 1.330 (6) | C21—H21 | 0.9300 |
O9—H36 | 0.8200 | C22—C23 | 1.475 (5) |
O1W—H1W1 | 0.84 (3) | C23—C24 | 1.386 (5) |
O1W—H1W2 | 0.84 (3) | C23—C28 | 1.398 (5) |
C1—C2 | 1.547 (4) | C24—C25 | 1.392 (7) |
C2—C14 | 1.518 (5) | C24—H24 | 0.9300 |
C2—C3 | 1.536 (4) | C25—C26 | 1.376 (7) |
C3—C4 | 1.378 (5) | C25—H25 | 0.9300 |
C3—C8 | 1.404 (5) | C26—C27 | 1.395 (6) |
C4—C5 | 1.397 (6) | C26—H26 | 0.9300 |
C4—H4 | 0.9300 | C27—C28 | 1.387 (5) |
C5—C6 | 1.380 (8) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C29—H29A | 0.9600 |
C6—C7 | 1.373 (8) | C29—H29B | 0.9600 |
C6—H6 | 0.9300 | C29—H29C | 0.9600 |
C7—C8 | 1.400 (5) | C30—H30A | 0.9600 |
C7—H7 | 0.9300 | C30—H30B | 0.9600 |
C8—C9 | 1.464 (6) | C30—H30C | 0.9600 |
C9—C10 | 1.399 (6) | C31—H31A | 0.9600 |
C9—C14 | 1.400 (5) | C31—H31B | 0.9600 |
C10—C11 | 1.364 (8) | C31—H31C | 0.9600 |
C10—H10 | 0.9300 | ||
O1—Cu1—O3 | 73.65 (8) | C11—C10—H10 | 120.4 |
O1—Cu1—O6 | 95.20 (8) | C11—C12—H12 | 119.5 |
O1—Cu1—O7 | 79.20 (8) | C12—C11—H11 | 119.6 |
O3—Cu1—O7 | 151.78 (9) | C12—C13—H13 | 120.7 |
O4—Cu1—O1 | 175.43 (8) | C13—C12—C11 | 121.1 (5) |
O4—Cu1—O3 | 109.39 (8) | C13—C12—H12 | 119.5 |
O4—Cu1—O6 | 81.51 (8) | C13—C14—C2 | 128.8 (3) |
O4—Cu1—O7 | 97.31 (9) | C13—C14—C9 | 120.8 (4) |
O4—Cu1—O1W | 90.84 (8) | C14—C2—C1 | 111.6 (2) |
O6—Cu1—O3 | 89.99 (9) | C14—C2—C3 | 102.2 (2) |
O6—Cu1—O7 | 84.97 (9) | C14—C9—C8 | 108.6 (3) |
O1W—Cu1—O1 | 92.41 (9) | C14—C13—C12 | 118.6 (5) |
O1W—Cu1—O3 | 92.93 (10) | C14—C13—H13 | 120.7 |
O1W—Cu1—O6 | 172.34 (8) | C15—O4—Cu1 | 118.41 (18) |
O1W—Cu1—O7 | 95.68 (10) | C16—O6—Cu1 | 116.01 (17) |
Cu1—O3—H32 | 136 (3) | C16—O6—H33 | 113 (3) |
Cu1—O6—H33 | 118 (3) | C17—C16—C15 | 111.0 (2) |
Cu1—O1W—H1W1 | 119 (2) | C17—C18—C19 | 118.2 (3) |
Cu1—O1W—H1W2 | 119 (2) | C17—C18—H18 | 120.9 |
O1—C1—C2 | 117.9 (2) | C17—C22—C21 | 119.5 (3) |
O2—C1—O1 | 123.3 (3) | C17—C22—C23 | 108.9 (3) |
O2—C1—C2 | 118.7 (3) | C18—C17—C16 | 128.8 (3) |
O3—C2—C1 | 107.9 (2) | C18—C17—C22 | 121.3 (3) |
O3—C2—C3 | 113.8 (2) | C18—C19—H19 | 119.4 |
O3—C2—C14 | 114.1 (3) | C19—C18—H18 | 120.9 |
O4—C15—C16 | 116.6 (2) | C19—C20—C21 | 121.0 (3) |
O5—C15—O4 | 123.9 (3) | C19—C20—H20 | 119.5 |
O5—C15—C16 | 119.5 (2) | C20—C19—C18 | 121.2 (4) |
O6—C16—C15 | 107.3 (2) | C20—C19—H19 | 119.4 |
O6—C16—C17 | 113.3 (2) | C20—C21—C22 | 119.0 (4) |
O6—C16—C28 | 111.7 (2) | C20—C21—H21 | 120.5 |
O7—C29—H29A | 109.5 | C21—C20—H20 | 119.5 |
O7—C29—H29B | 109.5 | C21—C22—C23 | 131.6 (3) |
O7—C29—H29C | 109.5 | C22—C17—C16 | 109.9 (3) |
O8—C30—H30A | 109.5 | C22—C21—H21 | 120.5 |
O8—C30—H30B | 109.5 | C23—C24—C25 | 118.6 (4) |
O8—C30—H30C | 109.5 | C23—C24—H24 | 120.7 |
O9—C31—H31A | 109.5 | C23—C28—C16 | 110.4 (3) |
O9—C31—H31B | 109.5 | C24—C23—C22 | 131.4 (4) |
O9—C31—H31C | 109.5 | C24—C23—C28 | 120.1 (4) |
C1—O1—Cu1 | 126.46 (18) | C24—C25—H25 | 119.4 |
C2—O3—Cu1 | 112.89 (16) | C25—C24—H24 | 120.7 |
C2—O3—H32 | 110 (3) | C25—C26—C27 | 120.6 (4) |
C3—C2—C1 | 107.0 (2) | C25—C26—H26 | 119.7 |
C3—C4—C5 | 118.2 (4) | C26—C25—C24 | 121.2 (4) |
C3—C4—H4 | 120.9 | C26—C25—H25 | 119.4 |
C3—C8—C9 | 109.4 (3) | C26—C27—H27 | 120.8 |
C4—C3—C2 | 128.8 (3) | C27—C26—H26 | 119.7 |
C4—C3—C8 | 121.9 (3) | C27—C28—C16 | 128.5 (3) |
C4—C5—H5 | 119.9 | C27—C28—C23 | 121.1 (3) |
C5—C4—H4 | 120.9 | C28—C16—C15 | 111.4 (2) |
C5—C6—C7 | 121.8 (4) | C28—C16—C17 | 102.2 (2) |
C5—C6—H6 | 119.1 | C28—C27—C26 | 118.3 (4) |
C6—C5—C4 | 120.3 (5) | C28—C27—H27 | 120.8 |
C6—C5—H5 | 119.9 | C28—C23—C22 | 108.5 (3) |
C6—C7—C8 | 119.1 (4) | C29—O7—H34 | 109.5 |
C6—C7—H7 | 120.5 | C30—O8—H35 | 109.5 |
C7—C6—H6 | 119.1 | C31—O9—H36 | 109.5 |
C7—C8—C3 | 118.8 (4) | H1W1—O1W—H1W2 | 111.4 (17) |
C7—C8—C9 | 131.8 (4) | H29A—C29—H29B | 109.5 |
C8—C3—C2 | 109.2 (3) | H29A—C29—H29C | 109.5 |
C8—C7—H7 | 120.5 | H29B—C29—H29C | 109.5 |
C9—C10—H10 | 120.4 | H30A—C30—H30B | 109.5 |
C9—C14—C2 | 110.4 (3) | H30A—C30—H30C | 109.5 |
C10—C9—C8 | 131.9 (4) | H30B—C30—H30C | 109.5 |
C10—C9—C14 | 119.5 (4) | H31A—C31—H31B | 109.5 |
C10—C11—C12 | 120.8 (5) | H31A—C31—H31C | 109.5 |
C10—C11—H11 | 119.6 | H31B—C31—H31C | 109.5 |
C11—C10—C9 | 119.3 (5) | ||
Cu1—O1—C1—O2 | 169.2 (2) | C4—C3—C8—C9 | 179.5 (3) |
Cu1—O1—C1—C2 | −13.9 (4) | C4—C5—C6—C7 | −0.8 (7) |
Cu1—O3—C2—C1 | −0.3 (3) | C5—C6—C7—C8 | 0.7 (7) |
Cu1—O3—C2—C3 | 118.3 (2) | C6—C7—C8—C3 | −0.3 (6) |
Cu1—O3—C2—C14 | −125.0 (2) | C6—C7—C8—C9 | −179.5 (4) |
Cu1—O4—C15—O5 | 177.2 (2) | C7—C8—C9—C10 | 2.2 (7) |
Cu1—O4—C15—C16 | −2.9 (3) | C7—C8—C9—C14 | −179.7 (4) |
Cu1—O6—C16—C15 | −3.7 (3) | C8—C3—C4—C5 | −0.2 (5) |
Cu1—O6—C16—C17 | 119.2 (2) | C8—C9—C10—C11 | 176.8 (4) |
Cu1—O6—C16—C28 | −126.0 (2) | C8—C9—C14—C2 | 2.2 (4) |
O1—Cu1—O3—C2 | −4.29 (19) | C8—C9—C14—C13 | −177.7 (3) |
O1—Cu1—O6—C16 | −174.77 (18) | C9—C10—C11—C12 | 0.3 (7) |
O1—C1—C2—O3 | 7.7 (4) | C10—C9—C14—C2 | −179.4 (3) |
O1—C1—C2—C3 | −115.2 (3) | C10—C9—C14—C13 | 0.7 (5) |
O1—C1—C2—C14 | 133.8 (3) | C10—C11—C12—C13 | 1.1 (8) |
O2—C1—C2—O3 | −175.2 (3) | C11—C12—C13—C14 | −1.6 (7) |
O2—C1—C2—C3 | 61.9 (4) | C12—C13—C14—C2 | −179.2 (4) |
O2—C1—C2—C14 | −49.1 (4) | C12—C13—C14—C9 | 0.7 (6) |
O3—Cu1—O1—C1 | 10.1 (2) | C14—C2—C3—C4 | −178.8 (3) |
O3—Cu1—O4—C15 | −86.4 (2) | C14—C2—C3—C8 | 4.8 (3) |
O3—Cu1—O6—C16 | 111.65 (18) | C14—C9—C10—C11 | −1.1 (6) |
O3—C2—C3—C4 | −55.2 (4) | C15—C16—C17—C18 | 61.4 (4) |
O3—C2—C3—C8 | 128.4 (3) | C15—C16—C17—C22 | −120.1 (3) |
O3—C2—C14—C9 | −127.6 (3) | C15—C16—C28—C23 | 120.3 (3) |
O3—C2—C14—C13 | 52.3 (4) | C15—C16—C28—C27 | −58.1 (4) |
O4—Cu1—O3—C2 | 172.13 (19) | C16—C17—C18—C19 | 179.1 (3) |
O4—Cu1—O6—C16 | 2.04 (18) | C16—C17—C22—C21 | −179.9 (3) |
O4—C15—C16—O6 | 4.2 (3) | C16—C17—C22—C23 | 0.3 (3) |
O4—C15—C16—C17 | −120.1 (3) | C17—C16—C28—C23 | 1.7 (3) |
O4—C15—C16—C28 | 126.7 (3) | C17—C16—C28—C27 | −176.7 (3) |
O5—C15—C16—O6 | −175.9 (2) | C17—C18—C19—C20 | −0.1 (5) |
O5—C15—C16—C17 | 59.8 (3) | C17—C22—C23—C24 | 179.3 (4) |
O5—C15—C16—C28 | −53.4 (3) | C17—C22—C23—C28 | 0.8 (4) |
O6—Cu1—O1—C1 | −78.4 (2) | C18—C17—C22—C21 | −1.2 (5) |
O6—Cu1—O3—C2 | 91.1 (2) | C18—C17—C22—C23 | 179.0 (3) |
O6—Cu1—O4—C15 | 0.6 (2) | C18—C19—C20—C21 | 0.2 (6) |
O6—C16—C17—C18 | −59.4 (4) | C19—C20—C21—C22 | −0.7 (6) |
O6—C16—C17—C22 | 119.1 (3) | C20—C21—C22—C17 | 1.2 (5) |
O6—C16—C28—C23 | −119.7 (3) | C20—C21—C22—C23 | −179.1 (4) |
O6—C16—C28—C27 | 61.8 (4) | C21—C22—C23—C24 | −0.4 (6) |
O1W—Cu1—O1—C1 | 102.4 (2) | C21—C22—C23—C28 | −178.9 (4) |
O1W—Cu1—O3—C2 | −95.9 (2) | C22—C17—C18—C19 | 0.6 (5) |
O1W—Cu1—O4—C15 | −179.8 (2) | C22—C23—C24—C25 | −176.8 (4) |
C1—C2—C3—C4 | 63.8 (4) | C22—C23—C28—C16 | −1.6 (3) |
C1—C2—C3—C8 | −112.6 (3) | C22—C23—C28—C27 | 177.0 (3) |
C1—C2—C14—C9 | 109.8 (3) | C23—C24—C25—C26 | 0.0 (7) |
C1—C2—C14—C13 | −70.3 (4) | C24—C23—C28—C16 | 179.7 (3) |
C2—C3—C4—C5 | −176.3 (3) | C24—C23—C28—C27 | −1.8 (5) |
C2—C3—C8—C9 | −3.8 (3) | C24—C25—C26—C27 | −1.6 (7) |
C2—C3—C8—C7 | 176.8 (3) | C25—C26—C27—C28 | 1.5 (6) |
C3—C2—C14—C9 | −4.2 (3) | C26—C27—C28—C16 | 178.5 (3) |
C3—C2—C14—C13 | 175.7 (3) | C26—C27—C28—C23 | 0.2 (5) |
C3—C4—C5—C6 | 0.6 (6) | C28—C16—C17—C18 | −179.8 (3) |
C3—C8—C9—C10 | −177.1 (4) | C28—C16—C17—C22 | −1.2 (3) |
C3—C8—C9—C14 | 1.1 (4) | C28—C23—C24—C25 | 1.6 (6) |
C4—C3—C8—C7 | 0.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H32···O8i | 0.85 (3) | 1.83 (3) | 2.671 (4) | 176 (4) |
O6—H33···O9ii | 0.84 (3) | 1.73 (3) | 2.567 (3) | 176 (4) |
O7—H34···O5ii | 0.82 | 2.41 | 3.175 (4) | 156 |
O8—H35···O2 | 0.82 | 1.97 | 2.693 (4) | 147 |
O9—H36···O5 | 0.82 | 2.02 | 2.797 (4) | 157 |
O1W—H1W2···O1iii | 0.84 (3) | 1.91 (3) | 2.737 (3) | 169 (4) |
O1W—H1W1···O4iv | 0.84 (3) | 1.87 (3) | 2.699 (3) | 170 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2. |
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