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metal-organic compounds
In the title mononuclear complex, [Cu(C8H5Cl2O3)2(C12H8N2)(H2O)], the CuII atom exists in a slightly distorted square-pyramidal coordination environment involving two carboxylate O atoms from two monodentate 2,4-dichlorophenoxyacetate ligands, two N atoms from a 1,10-phenanthroline ligand and one water molecule. A supramolecular structure is constructed by hydrogen-bonding and π–π stacking interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029163/gk2021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029163/gk2021Isup2.hkl |
CCDC reference: 621320
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.041
- wR factor = 0.112
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: RAPID-AUTO (Rigaku, 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.
Crystal data top
[Cu(C8H5Cl2O3)2(C12H8N2)(H2O)] | Z = 2 |
Mr = 701.80 | F(000) = 710 |
Triclinic, P1 | Dx = 1.660 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6317 (17) Å | Cell parameters from 10680 reflections |
b = 12.595 (3) Å | θ = 3.1–27.5° |
c = 14.491 (3) Å | µ = 1.21 mm−1 |
α = 111.07 (3)° | T = 295 K |
β = 95.34 (3)° | Prism, blue |
γ = 103.22 (3)° | 0.20 × 0.15 × 0.10 mm |
V = 1404.2 (7) Å3 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 6345 independent reflections |
Radiation source: fine-focus sealed tube | 4744 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −16→16 |
Tmin = 0.794, Tmax = 0.889 | l = −17→18 |
13741 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0461P)2 + 0.9049P] where P = (Fo2 + 2Fc2)/3 |
6345 reflections | (Δ/σ)max = 0.001 |
385 parameters | Δρmax = 0.40 e Å−3 |
3 restraints | Δρmin = −0.52 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.82139 (4) | 0.77380 (3) | 0.49726 (2) | 0.03767 (11) | |
Cl1 | 0.80911 (18) | 0.55951 (12) | −0.00631 (8) | 0.1054 (4) | |
Cl2 | 0.47841 (11) | 0.46623 (7) | 0.26475 (7) | 0.0624 (2) | |
Cl3 | 0.18837 (13) | 1.15524 (10) | 1.09429 (8) | 0.0806 (3) | |
Cl4 | 0.77288 (11) | 1.22261 (9) | 0.99135 (7) | 0.0746 (3) | |
N1 | 0.9527 (3) | 0.73088 (19) | 0.38873 (17) | 0.0376 (5) | |
N2 | 0.7937 (3) | 0.60307 (19) | 0.47716 (17) | 0.0380 (5) | |
O1w | 1.0545 (3) | 0.85730 (17) | 0.61717 (17) | 0.0482 (5) | |
O1 | 0.6809 (3) | 0.79873 (17) | 0.59608 (15) | 0.0478 (5) | |
O2 | 0.8491 (3) | 0.96983 (19) | 0.71038 (17) | 0.0570 (6) | |
O3 | 0.6183 (3) | 1.02301 (18) | 0.80845 (16) | 0.0540 (6) | |
O4 | 0.8053 (2) | 0.91330 (16) | 0.47212 (15) | 0.0424 (4) | |
O5 | 0.6803 (3) | 1.03376 (17) | 0.43912 (17) | 0.0513 (5) | |
O6 | 0.5313 (3) | 0.71996 (16) | 0.35554 (15) | 0.0470 (5) | |
C1 | 0.7160 (5) | 0.6071 (3) | 0.0960 (2) | 0.0605 (9) | |
C2 | 0.6402 (4) | 0.5264 (3) | 0.1329 (2) | 0.0559 (8) | |
C3 | 0.5749 (4) | 0.5669 (2) | 0.2179 (2) | 0.0442 (7) | |
C4 | 0.5869 (3) | 0.6867 (2) | 0.2668 (2) | 0.0420 (6) | |
C5 | 0.6579 (4) | 0.7642 (3) | 0.2250 (2) | 0.0524 (8) | |
C6 | 0.7241 (5) | 0.7241 (3) | 0.1400 (2) | 0.0610 (9) | |
C7 | 0.5195 (4) | 0.8397 (2) | 0.3972 (2) | 0.0489 (7) | |
C8 | 0.6811 (3) | 0.9352 (2) | 0.4394 (2) | 0.0395 (6) | |
C9 | 0.7169 (4) | 0.8957 (2) | 0.6746 (2) | 0.0430 (6) | |
C10 | 0.5704 (4) | 0.9132 (2) | 0.7228 (2) | 0.0458 (7) | |
C11 | 0.5110 (4) | 1.0468 (2) | 0.8703 (2) | 0.0412 (6) | |
C12 | 0.5704 (4) | 1.1427 (2) | 0.9628 (2) | 0.0444 (7) | |
C13 | 0.4729 (4) | 1.1743 (3) | 1.0318 (2) | 0.0502 (7) | |
C14 | 0.3121 (4) | 1.1113 (3) | 1.0075 (2) | 0.0487 (7) | |
C15 | 0.2485 (4) | 1.0181 (3) | 0.9162 (3) | 0.0545 (8) | |
C16 | 0.3480 (4) | 0.9862 (3) | 0.8475 (2) | 0.0501 (7) | |
C17 | 1.0317 (4) | 0.7990 (3) | 0.3466 (2) | 0.0425 (6) | |
C18 | 1.1157 (4) | 0.7560 (3) | 0.2703 (2) | 0.0484 (7) | |
C19 | 1.1192 (4) | 0.6405 (3) | 0.2375 (2) | 0.0510 (7) | |
C20 | 1.0376 (4) | 0.5653 (2) | 0.2801 (2) | 0.0431 (6) | |
C21 | 1.0301 (4) | 0.4424 (3) | 0.2518 (2) | 0.0531 (8) | |
C22 | 0.9480 (4) | 0.3773 (3) | 0.2971 (3) | 0.0558 (8) | |
C23 | 0.8639 (3) | 0.4270 (2) | 0.3758 (2) | 0.0439 (7) | |
C24 | 0.7757 (4) | 0.3649 (3) | 0.4264 (3) | 0.0520 (8) | |
C25 | 0.6992 (4) | 0.4220 (3) | 0.4993 (3) | 0.0530 (8) | |
C26 | 0.7118 (4) | 0.5419 (3) | 0.5234 (2) | 0.0458 (7) | |
C27 | 0.8688 (3) | 0.5469 (2) | 0.4041 (2) | 0.0357 (6) | |
C28 | 0.9559 (3) | 0.6157 (2) | 0.3562 (2) | 0.0365 (6) | |
H1w1 | 1.127 (3) | 0.894 (2) | 0.595 (3) | 0.072* | |
H1w2 | 1.010 (4) | 0.904 (2) | 0.655 (2) | 0.072* | |
H2A | 0.6332 | 0.4463 | 0.1013 | 0.067* | |
H5A | 0.6613 | 0.8438 | 0.2543 | 0.063* | |
H6A | 0.7737 | 0.7768 | 0.1130 | 0.073* | |
H7A | 0.4575 | 0.8470 | 0.4505 | 0.059* | |
H7B | 0.4595 | 0.8540 | 0.3450 | 0.059* | |
H10A | 0.4852 | 0.9140 | 0.6746 | 0.055* | |
H10B | 0.5287 | 0.8485 | 0.7432 | 0.055* | |
H13A | 0.5151 | 1.2373 | 1.0938 | 0.060* | |
H15A | 0.1391 | 0.9767 | 0.9005 | 0.065* | |
H16A | 0.3048 | 0.9234 | 0.7855 | 0.060* | |
H17A | 1.0311 | 0.8780 | 0.3688 | 0.051* | |
H18A | 1.1692 | 0.8056 | 0.2417 | 0.058* | |
H19A | 1.1757 | 0.6117 | 0.1868 | 0.061* | |
H21A | 1.0830 | 0.4070 | 0.2012 | 0.064* | |
H22A | 0.9456 | 0.2979 | 0.2769 | 0.067* | |
H24A | 0.7694 | 0.2854 | 0.4105 | 0.062* | |
H25A | 0.6392 | 0.3813 | 0.5325 | 0.064* | |
H26A | 0.6607 | 0.5801 | 0.5738 | 0.055* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0432 (2) | 0.02958 (17) | 0.04026 (19) | 0.01107 (13) | 0.01490 (14) | 0.01162 (13) |
Cl1 | 0.1349 (11) | 0.1145 (10) | 0.0642 (6) | 0.0403 (8) | 0.0575 (7) | 0.0197 (6) |
Cl2 | 0.0729 (6) | 0.0393 (4) | 0.0615 (5) | 0.0023 (4) | 0.0186 (4) | 0.0115 (3) |
Cl3 | 0.0756 (7) | 0.0861 (7) | 0.0817 (7) | 0.0267 (5) | 0.0468 (6) | 0.0249 (5) |
Cl4 | 0.0522 (5) | 0.0683 (6) | 0.0687 (6) | −0.0053 (4) | 0.0158 (4) | −0.0001 (4) |
N1 | 0.0380 (12) | 0.0359 (12) | 0.0388 (12) | 0.0099 (9) | 0.0096 (10) | 0.0143 (10) |
N2 | 0.0386 (12) | 0.0303 (11) | 0.0435 (12) | 0.0091 (9) | 0.0091 (10) | 0.0127 (9) |
O1w | 0.0450 (12) | 0.0420 (11) | 0.0560 (13) | 0.0128 (9) | 0.0109 (10) | 0.0169 (10) |
O1 | 0.0535 (13) | 0.0364 (10) | 0.0488 (11) | 0.0093 (9) | 0.0228 (10) | 0.0101 (9) |
O2 | 0.0545 (14) | 0.0460 (12) | 0.0556 (13) | 0.0043 (10) | 0.0239 (11) | 0.0056 (10) |
O3 | 0.0523 (13) | 0.0420 (11) | 0.0527 (12) | 0.0078 (9) | 0.0232 (10) | 0.0018 (9) |
O4 | 0.0404 (11) | 0.0343 (10) | 0.0540 (12) | 0.0129 (8) | 0.0116 (9) | 0.0169 (9) |
O5 | 0.0518 (13) | 0.0408 (11) | 0.0693 (14) | 0.0204 (9) | 0.0194 (11) | 0.0243 (10) |
O6 | 0.0548 (13) | 0.0340 (10) | 0.0456 (11) | 0.0118 (9) | 0.0173 (10) | 0.0068 (8) |
C1 | 0.074 (2) | 0.070 (2) | 0.0362 (16) | 0.0255 (18) | 0.0163 (16) | 0.0149 (15) |
C2 | 0.062 (2) | 0.0490 (18) | 0.0459 (17) | 0.0177 (15) | 0.0096 (15) | 0.0051 (14) |
C3 | 0.0456 (17) | 0.0402 (15) | 0.0396 (15) | 0.0108 (12) | 0.0048 (12) | 0.0090 (12) |
C4 | 0.0403 (16) | 0.0440 (15) | 0.0382 (14) | 0.0122 (12) | 0.0050 (12) | 0.0125 (12) |
C5 | 0.069 (2) | 0.0460 (17) | 0.0430 (16) | 0.0194 (15) | 0.0090 (15) | 0.0172 (14) |
C6 | 0.080 (3) | 0.069 (2) | 0.0423 (17) | 0.0214 (18) | 0.0138 (17) | 0.0298 (16) |
C7 | 0.0454 (17) | 0.0412 (16) | 0.0557 (18) | 0.0156 (13) | 0.0155 (14) | 0.0105 (13) |
C8 | 0.0469 (16) | 0.0345 (14) | 0.0389 (14) | 0.0175 (12) | 0.0193 (12) | 0.0103 (11) |
C9 | 0.0541 (18) | 0.0390 (15) | 0.0392 (15) | 0.0146 (13) | 0.0188 (13) | 0.0159 (12) |
C10 | 0.0497 (17) | 0.0397 (15) | 0.0418 (15) | 0.0112 (13) | 0.0132 (13) | 0.0086 (12) |
C11 | 0.0448 (16) | 0.0373 (14) | 0.0442 (15) | 0.0154 (12) | 0.0156 (13) | 0.0149 (12) |
C12 | 0.0458 (17) | 0.0385 (15) | 0.0451 (16) | 0.0086 (12) | 0.0119 (13) | 0.0133 (12) |
C13 | 0.061 (2) | 0.0473 (17) | 0.0402 (15) | 0.0144 (14) | 0.0144 (14) | 0.0144 (13) |
C14 | 0.0537 (19) | 0.0494 (17) | 0.0516 (17) | 0.0209 (14) | 0.0233 (15) | 0.0224 (14) |
C15 | 0.0436 (18) | 0.0522 (18) | 0.066 (2) | 0.0120 (14) | 0.0153 (15) | 0.0216 (16) |
C16 | 0.0486 (18) | 0.0441 (16) | 0.0490 (17) | 0.0098 (13) | 0.0093 (14) | 0.0105 (13) |
C17 | 0.0438 (16) | 0.0402 (15) | 0.0450 (15) | 0.0095 (12) | 0.0105 (13) | 0.0193 (12) |
C18 | 0.0480 (18) | 0.0533 (18) | 0.0449 (16) | 0.0104 (14) | 0.0144 (14) | 0.0213 (14) |
C19 | 0.0484 (18) | 0.0595 (19) | 0.0388 (15) | 0.0136 (14) | 0.0150 (13) | 0.0113 (14) |
C20 | 0.0414 (16) | 0.0426 (15) | 0.0373 (14) | 0.0136 (12) | 0.0052 (12) | 0.0060 (12) |
C21 | 0.0559 (19) | 0.0429 (16) | 0.0514 (18) | 0.0212 (14) | 0.0149 (15) | 0.0025 (14) |
C22 | 0.063 (2) | 0.0334 (15) | 0.0594 (19) | 0.0161 (14) | 0.0097 (16) | 0.0044 (14) |
C23 | 0.0407 (16) | 0.0330 (14) | 0.0492 (16) | 0.0080 (12) | 0.0020 (13) | 0.0093 (12) |
C24 | 0.0495 (18) | 0.0324 (15) | 0.068 (2) | 0.0056 (13) | 0.0030 (15) | 0.0180 (14) |
C25 | 0.0499 (18) | 0.0410 (16) | 0.067 (2) | 0.0019 (13) | 0.0073 (16) | 0.0282 (15) |
C26 | 0.0444 (17) | 0.0443 (16) | 0.0507 (17) | 0.0091 (13) | 0.0134 (14) | 0.0219 (13) |
C27 | 0.0352 (14) | 0.0272 (12) | 0.0388 (14) | 0.0094 (10) | 0.0040 (11) | 0.0065 (10) |
C28 | 0.0388 (15) | 0.0294 (13) | 0.0362 (13) | 0.0098 (11) | 0.0041 (11) | 0.0076 (10) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.947 (2) | C7—H7B | 0.9700 |
Cu1—O4 | 1.950 (2) | C9—C10 | 1.522 (4) |
Cu1—N1 | 2.013 (2) | C10—H10A | 0.9700 |
Cu1—N2 | 2.017 (2) | C10—H10B | 0.9700 |
Cu1—O1w | 2.289 (2) | C11—C12 | 1.394 (4) |
Cl1—C1 | 1.734 (3) | C11—C16 | 1.382 (4) |
Cl2—C3 | 1.733 (3) | C12—C13 | 1.374 (4) |
Cl3—C14 | 1.746 (3) | C13—C14 | 1.373 (5) |
Cl4—C12 | 1.732 (3) | C13—H13A | 0.9300 |
O1—C9 | 1.282 (3) | C14—C15 | 1.372 (5) |
O2—C9 | 1.224 (4) | C15—C16 | 1.386 (4) |
O4—C8 | 1.258 (3) | C15—H15A | 0.9300 |
O5—C8 | 1.245 (3) | C16—H16A | 0.9300 |
N1—C17 | 1.327 (3) | C17—C18 | 1.393 (4) |
N1—C28 | 1.362 (3) | C17—H17A | 0.9300 |
N2—C26 | 1.324 (4) | C18—C19 | 1.366 (4) |
N2—C27 | 1.356 (3) | C18—H18A | 0.9300 |
O1w—H1w1 | 0.85 (3) | C19—C20 | 1.404 (4) |
O1w—H1w2 | 0.84 (3) | C19—H19A | 0.9300 |
O3—C10 | 1.426 (3) | C20—C21 | 1.436 (4) |
O3—C11 | 1.357 (3) | C20—C28 | 1.401 (4) |
O6—C4 | 1.371 (3) | C21—C22 | 1.346 (5) |
O6—C7 | 1.441 (3) | C21—H21A | 0.9300 |
C1—C2 | 1.379 (5) | C22—C23 | 1.438 (4) |
C1—C6 | 1.361 (5) | C22—H22A | 0.9300 |
C2—C3 | 1.380 (4) | C23—C24 | 1.406 (4) |
C2—H2A | 0.9300 | C23—C27 | 1.404 (4) |
C3—C4 | 1.391 (4) | C24—C25 | 1.366 (5) |
C4—C5 | 1.384 (4) | C24—H24A | 0.9300 |
C5—C6 | 1.384 (4) | C25—C26 | 1.398 (4) |
C5—H5A | 0.9300 | C25—H25A | 0.9300 |
C6—H6A | 0.9300 | C26—H26A | 0.9300 |
C7—C8 | 1.520 (4) | C27—C28 | 1.425 (4) |
C7—H7A | 0.9700 | ||
N1—Cu1—N2 | 81.48 (9) | C9—C10—H10A | 109.9 |
N1—Cu1—O1w | 90.02 (9) | C9—C10—H10B | 109.9 |
N2—Cu1—O1w | 98.15 (9) | C11—O3—C10 | 117.8 (2) |
O1—Cu1—N1 | 174.21 (8) | C11—C12—Cl4 | 118.8 (2) |
O1—Cu1—N2 | 93.55 (9) | C11—C16—C15 | 120.7 (3) |
O1—Cu1—O4 | 92.87 (9) | C11—C16—H16A | 119.7 |
O1—Cu1—O1w | 93.65 (9) | C12—C13—H13A | 120.6 |
O4—Cu1—N1 | 90.97 (9) | C13—C12—C11 | 121.7 (3) |
O4—Cu1—N2 | 161.12 (9) | C13—C12—Cl4 | 119.5 (2) |
O4—Cu1—O1w | 99.14 (8) | C13—C14—Cl3 | 118.4 (2) |
Cu1—O1w—H1w1 | 109 (3) | C14—C13—C12 | 118.9 (3) |
Cu1—O1w—H1w2 | 90 (3) | C14—C13—H13A | 120.6 |
N1—C17—C18 | 122.0 (3) | C14—C15—C16 | 119.7 (3) |
N1—C17—H17A | 119.0 | C14—C15—H15A | 120.2 |
N1—C28—C20 | 123.4 (3) | C15—C14—Cl3 | 120.6 (3) |
N1—C28—C27 | 115.8 (2) | C15—C14—C13 | 121.0 (3) |
N2—C26—C25 | 122.5 (3) | C15—C16—H16A | 119.7 |
N2—C26—H26A | 118.7 | C16—C11—C12 | 118.0 (3) |
N2—C27—C23 | 122.9 (3) | C16—C15—H15A | 120.2 |
N2—C27—C28 | 116.8 (2) | C17—N1—C28 | 118.3 (2) |
O1—C9—C10 | 111.8 (3) | C17—N1—Cu1 | 128.48 (19) |
O2—C9—O1 | 127.5 (3) | C17—C18—H18A | 120.1 |
O2—C9—C10 | 120.7 (2) | C18—C17—H17A | 119.0 |
O3—C10—C9 | 108.8 (2) | C18—C19—C20 | 120.1 (3) |
O3—C10—H10A | 109.9 | C18—C19—H19A | 119.9 |
O3—C10—H10B | 109.9 | C19—C18—C17 | 119.8 (3) |
O3—C11—C12 | 116.7 (3) | C19—C18—H18A | 120.1 |
O3—C11—C16 | 125.3 (3) | C19—C20—C21 | 125.7 (3) |
O4—C8—C7 | 120.8 (2) | C20—C19—H19A | 119.9 |
O5—C8—O4 | 123.6 (3) | C20—C21—H21A | 119.3 |
O5—C8—C7 | 115.5 (3) | C20—C28—C27 | 120.8 (2) |
O6—C4—C3 | 116.9 (3) | C21—C22—C23 | 121.9 (3) |
O6—C4—C5 | 124.6 (3) | C21—C22—H22A | 119.1 |
O6—C7—C8 | 114.9 (2) | C22—C21—C20 | 121.3 (3) |
O6—C7—H7A | 108.5 | C22—C21—H21A | 119.3 |
O6—C7—H7B | 108.5 | C23—C22—H22A | 119.1 |
C1—C2—C3 | 118.5 (3) | C23—C24—H24A | 120.2 |
C1—C2—H2A | 120.7 | C23—C27—C28 | 120.3 (2) |
C1—C6—C5 | 119.6 (3) | C24—C23—C22 | 125.2 (3) |
C1—C6—H6A | 120.2 | C24—C25—C26 | 119.5 (3) |
C2—C1—Cl1 | 119.3 (3) | C24—C25—H25A | 120.2 |
C2—C3—C4 | 121.2 (3) | C25—C24—C23 | 119.6 (3) |
C2—C3—Cl2 | 119.0 (2) | C25—C24—H24A | 120.2 |
C3—C2—H2A | 120.7 | C25—C26—H26A | 118.7 |
C4—O6—C7 | 116.5 (2) | C26—N2—Cu1 | 128.8 (2) |
C4—C3—Cl2 | 119.8 (2) | C26—N2—C27 | 118.4 (2) |
C4—C5—H5A | 119.8 | C26—C25—H25A | 120.2 |
C5—C4—C3 | 118.5 (3) | C27—N2—Cu1 | 112.74 (18) |
C5—C6—H6A | 120.2 | C27—C23—C22 | 117.8 (3) |
C6—C1—Cl1 | 119.1 (3) | C27—C23—C24 | 117.1 (3) |
C6—C1—C2 | 121.6 (3) | C28—N1—Cu1 | 113.17 (18) |
C6—C5—C4 | 120.5 (3) | C28—C20—C19 | 116.3 (3) |
C6—C5—H5A | 119.8 | C28—C20—C21 | 117.9 (3) |
C8—O4—Cu1 | 128.82 (18) | H1w1—O1w—H1w2 | 110.9 (17) |
C8—C7—H7A | 108.5 | H7A—C7—H7B | 107.5 |
C8—C7—H7B | 108.5 | H10A—C10—H10B | 108.3 |
C9—O1—Cu1 | 120.90 (19) | ||
Cu1—N1—C17—C18 | −178.8 (2) | C2—C1—C6—C5 | 1.4 (6) |
Cu1—N2—C26—C25 | 178.0 (2) | C2—C3—C4—O6 | −174.3 (3) |
Cu1—N1—C28—C20 | 179.0 (2) | C2—C3—C4—C5 | 3.6 (5) |
Cu1—N2—C27—C23 | −178.9 (2) | C3—C4—C5—C6 | −3.8 (5) |
Cu1—N2—C27—C28 | 1.4 (3) | C4—O6—C7—C8 | −70.7 (3) |
Cu1—O1—C9—O2 | −17.5 (4) | C4—C5—C6—C1 | 1.4 (5) |
Cu1—O1—C9—C10 | 161.8 (2) | C6—C1—C2—C3 | −1.6 (5) |
Cu1—O4—C8—O5 | 169.6 (2) | C7—O6—C4—C3 | −170.3 (3) |
Cu1—O4—C8—C7 | −10.3 (4) | C7—O6—C4—C5 | 11.9 (4) |
Cl1—C1—C2—C3 | 176.3 (3) | C10—O3—C11—C12 | 168.1 (3) |
Cl1—C1—C6—C5 | −176.5 (3) | C10—O3—C11—C16 | −13.9 (4) |
Cl2—C3—C4—O6 | 5.0 (4) | C11—O3—C10—C9 | −170.6 (2) |
Cl2—C3—C4—C5 | −177.0 (2) | C11—C12—C13—C14 | −1.5 (5) |
Cl3—C14—C15—C16 | 178.6 (3) | C12—C11—C16—C15 | −1.8 (5) |
Cl4—C12—C13—C14 | 179.0 (2) | C12—C13—C14—Cl3 | −178.1 (2) |
N1—Cu1—N2—C26 | −179.8 (3) | C12—C13—C14—C15 | 0.0 (5) |
N1—Cu1—N2—C27 | −1.27 (18) | C13—C14—C15—C16 | 0.6 (5) |
N1—Cu1—O4—C8 | 115.1 (2) | C14—C15—C16—C11 | 0.3 (5) |
N1—C17—C18—C19 | −0.6 (5) | C16—C11—C12—C13 | 2.4 (5) |
N2—Cu1—N1—C17 | −179.6 (3) | C16—C11—C12—Cl4 | −178.1 (2) |
N2—Cu1—N1—C28 | 0.97 (18) | C17—N1—C28—C20 | −0.4 (4) |
N2—Cu1—O1—C9 | 139.7 (2) | C17—N1—C28—C27 | −180.0 (2) |
N2—Cu1—O4—C8 | 49.2 (4) | C17—C18—C19—C20 | 0.4 (5) |
N2—C27—C28—N1 | −0.6 (4) | C18—C19—C20—C21 | 179.2 (3) |
N2—C27—C28—C20 | 179.8 (2) | C18—C19—C20—C28 | −0.2 (4) |
O1—Cu1—N2—C26 | −2.8 (3) | C19—C20—C21—C22 | −179.8 (3) |
O1—Cu1—N2—C27 | 175.7 (2) | C19—C20—C28—N1 | 0.2 (4) |
O1—Cu1—O4—C8 | −60.5 (2) | C19—C20—C28—C27 | 179.7 (3) |
O1—C9—C10—O3 | −179.2 (2) | C20—C21—C22—C23 | 0.0 (5) |
O2—C9—C10—O3 | 0.2 (4) | C21—C20—C28—N1 | −179.2 (3) |
O3—C11—C12—C13 | −179.4 (3) | C21—C20—C28—C27 | 0.3 (4) |
O3—C11—C12—Cl4 | 0.0 (4) | C21—C22—C23—C24 | 179.9 (3) |
O3—C11—C16—C15 | −179.8 (3) | C21—C22—C23—C27 | 0.4 (5) |
O4—Cu1—N1—C17 | 17.7 (3) | C22—C23—C24—C25 | −179.2 (3) |
O4—Cu1—N1—C28 | −161.7 (2) | C22—C23—C27—N2 | 179.8 (3) |
O4—Cu1—N2—C26 | −112.4 (3) | C22—C23—C27—C28 | −0.5 (4) |
O4—Cu1—N2—C27 | 66.1 (3) | C23—C24—C25—C26 | −0.9 (5) |
O4—Cu1—O1—C9 | −58.1 (2) | C23—C27—C28—N1 | 179.7 (2) |
O6—C4—C5—C6 | 174.0 (3) | C23—C27—C28—C20 | 0.1 (4) |
O6—C7—C8—O4 | −26.9 (4) | C24—C23—C27—N2 | 0.3 (4) |
O6—C7—C8—O5 | 153.2 (3) | C24—C23—C27—C28 | 180.0 (3) |
O1w—Cu1—N1—C17 | −81.4 (2) | C24—C25—C26—N2 | 1.0 (5) |
O1w—Cu1—N1—C28 | 99.20 (19) | C26—N2—C27—C23 | −0.2 (4) |
O1w—Cu1—N2—C26 | 91.4 (3) | C26—N2—C27—C28 | −179.9 (3) |
O1w—Cu1—N2—C27 | −90.1 (2) | C27—N2—C26—C25 | −0.4 (4) |
O1w—Cu1—O1—C9 | 41.3 (2) | C27—C23—C24—C25 | 0.3 (4) |
O1w—Cu1—O4—C8 | −154.7 (2) | C28—N1—C17—C18 | 0.6 (4) |
C1—C2—C3—C4 | −1.0 (5) | C28—C20—C21—C22 | −0.4 (5) |
C1—C2—C3—Cl2 | 179.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O5i | 0.85 (3) | 1.90 (3) | 2.739 (3) | 168 (4) |
O1w—H1w2···O2 | 0.84 (3) | 1.88 (3) | 2.682 (3) | 161 (3) |
Symmetry code: (i) −x+2, −y+2, −z+1. |
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