In the title one-dimensional coordination polymer {systematic name:
catena-poly[[[aqua(1,10-phenanthroline-κ
2N,
N′)copper(II)]-μ-phenylenebis(oxyacetato)-κ
2O:
O′] dihydrate]}, {[Cu(C
10H
8O
6)(C
12H
8N
2)(H
2O)]·2H
2O}
n, the Cu
II atom has a distorted square-pyramidal coordination geometry, defined by two carboxyl O-atom donors from two benzene-1,3-dioxyacetate groups, two N-atom donors from the 1,10-phenanthroline ligand and one water molecule. The Cu
II ions are bridged by benzene-1,3-dioxyacetate dianions (1,3-BDOA
2−), resulting in a one-dimensional chain structure. The intrachain Cu
Cu separation is 9.769 (4) Å. The chains are linked into a three-dimensional supramolecular network
via hydrogen bonds and π–π stacking interactions.
Supporting information
CCDC reference: 258640
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.105
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT417_ALERT_2_C Short Inter D-H..H-D H1W1 .. H3W2 .. 2.14 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
1 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
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: ORTEPII (Johnson, 1976); molecular graphics: SHELXL97.
catena-poly[[[aqua(1,10-phenanthroline-
κ2N,
N')copper(II)]- µ-phenylenebis(oxyacetato)-
κ2O:
O'] dihydrate]
top
Crystal data top
[Cu(C10H8O6)(C12H8N2)(H2O)]·2H2O | F(000) = 1076 |
Mr = 521.97 | Dx = 1.555 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 20290 reflections |
a = 9.0034 (10) Å | θ = 3.4–27.5° |
b = 19.4609 (19) Å | µ = 1.04 mm−1 |
c = 12.7448 (13) Å | T = 293 K |
β = 93.005 (5)° | Prism, blue |
V = 2230.0 (4) Å3 | 0.38 × 0.24 × 0.18 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 5070 independent reflections |
Radiation source: fine-focus sealed tube | 4250 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 10 pixels mm-1 | θmax = 27.4°, θmin = 3.0° |
ω scan | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −23→25 |
Tmin = 0.694, Tmax = 0.835 | l = −16→16 |
21197 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0597P)2 + 0.6427P] where P = (Fo2 + 2Fc2)/3 |
5070 reflections | (Δ/σ)max = 0.002 |
325 parameters | Δρmax = 0.48 e Å−3 |
9 restraints | Δρmin = −0.35 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.32504 (3) | 0.605672 (13) | 0.675324 (18) | 0.04435 (10) | |
N1 | 0.25537 (19) | 0.52915 (9) | 0.57837 (14) | 0.0480 (4) | |
N2 | 0.42594 (18) | 0.63643 (9) | 0.54539 (13) | 0.0440 (4) | |
O1 | 0.40951 (17) | 0.68322 (8) | 0.75566 (11) | 0.0530 (3) | |
O2 | 0.5641 (2) | 0.62619 (9) | 0.86637 (16) | 0.0768 (5) | |
O3 | 0.51529 (18) | 0.80641 (8) | 0.82761 (12) | 0.0566 (4) | |
O4 | 0.62290 (19) | 0.94901 (8) | 0.55068 (12) | 0.0604 (4) | |
O5 | 0.76771 (19) | 0.94720 (8) | 0.29524 (13) | 0.0588 (4) | |
O6 | 0.5966 (2) | 0.87958 (9) | 0.36149 (14) | 0.0641 (4) | |
O1W | 0.10426 (18) | 0.66723 (9) | 0.65568 (14) | 0.0602 (4) | |
O2W | 0.8364 (2) | 0.64805 (12) | 0.97327 (16) | 0.0776 (5) | |
O3W | 0.24009 (18) | 0.79518 (10) | 0.65305 (15) | 0.0647 (4) | |
C1 | 0.1642 (3) | 0.47703 (12) | 0.5960 (2) | 0.0612 (6) | |
C2 | 0.1268 (3) | 0.42765 (13) | 0.5200 (3) | 0.0730 (7) | |
C3 | 0.1856 (3) | 0.43103 (13) | 0.4247 (2) | 0.0699 (7) | |
C4 | 0.2841 (3) | 0.48478 (11) | 0.40259 (19) | 0.0560 (5) | |
C5 | 0.3564 (3) | 0.49284 (14) | 0.30633 (19) | 0.0668 (7) | |
C6 | 0.4476 (3) | 0.54595 (15) | 0.29117 (18) | 0.0652 (7) | |
C7 | 0.4740 (2) | 0.59800 (12) | 0.36936 (17) | 0.0526 (5) | |
C8 | 0.5621 (3) | 0.65678 (14) | 0.35777 (19) | 0.0622 (6) | |
C9 | 0.5774 (3) | 0.70328 (13) | 0.4369 (2) | 0.0619 (6) | |
C10 | 0.5093 (2) | 0.69147 (12) | 0.53067 (18) | 0.0520 (5) | |
C11 | 0.4072 (2) | 0.59065 (11) | 0.46552 (16) | 0.0445 (4) | |
C12 | 0.3124 (2) | 0.53321 (10) | 0.48275 (16) | 0.0460 (4) | |
C13 | 0.5043 (2) | 0.67913 (11) | 0.83265 (16) | 0.0507 (5) | |
C14 | 0.5398 (3) | 0.74633 (11) | 0.89005 (17) | 0.0560 (5) | |
C15 | 0.6133 (2) | 0.81880 (11) | 0.75044 (16) | 0.0490 (5) | |
C16 | 0.7370 (2) | 0.77859 (12) | 0.73300 (19) | 0.0559 (5) | |
C17 | 0.8236 (3) | 0.79661 (14) | 0.6510 (2) | 0.0611 (6) | |
C18 | 0.7915 (2) | 0.85208 (13) | 0.58719 (18) | 0.0571 (5) | |
C19 | 0.6677 (2) | 0.89199 (11) | 0.60575 (17) | 0.0493 (5) | |
C20 | 0.5789 (2) | 0.87477 (11) | 0.68733 (16) | 0.0491 (5) | |
C21 | 0.7082 (3) | 0.97081 (12) | 0.46584 (18) | 0.0580 (6) | |
C22 | 0.6863 (2) | 0.92737 (11) | 0.36723 (17) | 0.0503 (5) | |
H1 | 0.1239 | 0.4735 | 0.6615 | 0.073* | |
H2 | 0.0615 | 0.3924 | 0.5349 | 0.088* | |
H3 | 0.1612 | 0.3980 | 0.3739 | 0.084* | |
H5 | 0.3400 | 0.4606 | 0.2531 | 0.080* | |
H6 | 0.4949 | 0.5491 | 0.2282 | 0.078* | |
H8 | 0.6100 | 0.6638 | 0.2958 | 0.075* | |
H9 | 0.6333 | 0.7429 | 0.4284 | 0.074* | |
H10 | 0.5227 | 0.7232 | 0.5849 | 0.062* | |
H14A | 0.4793 | 0.7492 | 0.9507 | 0.067* | |
H14B | 0.6432 | 0.7455 | 0.9156 | 0.067* | |
H16 | 0.7609 | 0.7408 | 0.7752 | 0.067* | |
H17 | 0.9069 | 0.7702 | 0.6385 | 0.073* | |
H18 | 0.8517 | 0.8628 | 0.5324 | 0.068* | |
H20 | 0.4955 | 0.9012 | 0.6996 | 0.059* | |
H21A | 0.8127 | 0.9700 | 0.4887 | 0.070* | |
H21B | 0.6822 | 1.0180 | 0.4486 | 0.070* | |
H1W1 | 0.143 (3) | 0.7068 (9) | 0.651 (2) | 0.090* | |
H1W2 | 0.083 (3) | 0.6604 (14) | 0.7195 (11) | 0.090* | |
H2W1 | 0.763 (2) | 0.636 (2) | 0.932 (2) | 0.116* | |
H2W2 | 0.916 (2) | 0.6322 (19) | 0.950 (3) | 0.116* | |
H3W1 | 0.273 (3) | 0.8172 (16) | 0.6016 (17) | 0.097* | |
H3W2 | 0.313 (2) | 0.7805 (16) | 0.692 (2) | 0.097* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.04480 (15) | 0.04835 (16) | 0.04016 (15) | 0.00322 (10) | 0.00490 (10) | −0.00039 (10) |
N1 | 0.0471 (9) | 0.0454 (9) | 0.0514 (10) | 0.0020 (7) | 0.0011 (7) | 0.0038 (7) |
N2 | 0.0440 (8) | 0.0451 (9) | 0.0428 (8) | 0.0037 (7) | 0.0027 (7) | −0.0007 (7) |
O1 | 0.0567 (8) | 0.0573 (9) | 0.0442 (8) | −0.0006 (7) | −0.0046 (6) | −0.0014 (6) |
O2 | 0.0845 (12) | 0.0568 (10) | 0.0854 (13) | 0.0150 (9) | −0.0324 (10) | −0.0128 (9) |
O3 | 0.0698 (9) | 0.0519 (8) | 0.0490 (8) | 0.0052 (7) | 0.0120 (7) | 0.0013 (7) |
O4 | 0.0730 (10) | 0.0590 (9) | 0.0508 (9) | 0.0131 (8) | 0.0191 (7) | 0.0040 (7) |
O5 | 0.0676 (9) | 0.0588 (9) | 0.0518 (9) | −0.0082 (8) | 0.0202 (7) | −0.0047 (7) |
O6 | 0.0660 (10) | 0.0689 (10) | 0.0590 (10) | −0.0143 (8) | 0.0176 (8) | −0.0077 (8) |
O1W | 0.0522 (9) | 0.0623 (10) | 0.0654 (10) | 0.0061 (7) | −0.0040 (8) | 0.0003 (8) |
O2W | 0.0550 (10) | 0.1023 (15) | 0.0750 (12) | 0.0125 (10) | −0.0027 (9) | −0.0266 (11) |
O3W | 0.0519 (9) | 0.0778 (12) | 0.0652 (11) | 0.0076 (8) | 0.0097 (7) | 0.0115 (9) |
C1 | 0.0593 (13) | 0.0552 (13) | 0.0692 (15) | −0.0025 (11) | 0.0026 (11) | 0.0107 (11) |
C2 | 0.0723 (16) | 0.0507 (14) | 0.094 (2) | −0.0110 (12) | −0.0118 (15) | 0.0055 (13) |
C3 | 0.0738 (16) | 0.0493 (13) | 0.0838 (19) | 0.0038 (12) | −0.0225 (14) | −0.0104 (12) |
C4 | 0.0581 (12) | 0.0493 (12) | 0.0587 (13) | 0.0132 (10) | −0.0134 (10) | −0.0086 (10) |
C5 | 0.0776 (16) | 0.0703 (16) | 0.0507 (13) | 0.0218 (14) | −0.0134 (11) | −0.0175 (11) |
C6 | 0.0719 (15) | 0.0833 (18) | 0.0402 (11) | 0.0236 (14) | 0.0010 (10) | −0.0046 (11) |
C7 | 0.0521 (11) | 0.0660 (14) | 0.0397 (10) | 0.0152 (10) | 0.0020 (9) | 0.0030 (9) |
C8 | 0.0583 (13) | 0.0793 (16) | 0.0499 (12) | 0.0086 (12) | 0.0124 (10) | 0.0152 (12) |
C9 | 0.0557 (12) | 0.0642 (14) | 0.0666 (15) | −0.0044 (11) | 0.0098 (11) | 0.0139 (12) |
C10 | 0.0519 (11) | 0.0513 (12) | 0.0528 (12) | −0.0005 (9) | 0.0040 (9) | 0.0018 (9) |
C11 | 0.0426 (10) | 0.0486 (11) | 0.0423 (10) | 0.0112 (8) | 0.0006 (8) | 0.0004 (8) |
C12 | 0.0456 (10) | 0.0450 (10) | 0.0466 (11) | 0.0100 (8) | −0.0042 (8) | −0.0014 (8) |
C13 | 0.0542 (11) | 0.0551 (12) | 0.0425 (10) | 0.0046 (10) | 0.0000 (9) | −0.0049 (9) |
C14 | 0.0738 (14) | 0.0530 (12) | 0.0408 (11) | 0.0010 (11) | 0.0002 (10) | −0.0010 (9) |
C15 | 0.0526 (11) | 0.0505 (11) | 0.0434 (10) | −0.0013 (9) | −0.0005 (8) | −0.0064 (9) |
C16 | 0.0537 (12) | 0.0579 (13) | 0.0554 (13) | 0.0060 (10) | −0.0047 (10) | −0.0004 (10) |
C17 | 0.0488 (11) | 0.0683 (15) | 0.0659 (14) | 0.0129 (10) | 0.0010 (10) | −0.0041 (12) |
C18 | 0.0516 (11) | 0.0674 (14) | 0.0527 (12) | 0.0035 (10) | 0.0078 (10) | −0.0060 (11) |
C19 | 0.0539 (11) | 0.0523 (12) | 0.0415 (10) | 0.0016 (9) | 0.0010 (9) | −0.0058 (8) |
C20 | 0.0504 (11) | 0.0513 (11) | 0.0459 (11) | 0.0040 (9) | 0.0050 (9) | −0.0062 (9) |
C21 | 0.0722 (14) | 0.0529 (12) | 0.0502 (12) | −0.0030 (11) | 0.0167 (11) | −0.0010 (10) |
C22 | 0.0527 (11) | 0.0496 (12) | 0.0493 (11) | 0.0049 (9) | 0.0092 (9) | 0.0018 (9) |
Geometric parameters (Å, º) top
Cu1—N1 | 2.014 (2) | C4—C5 | 1.427 (4) |
Cu1—N2 | 2.021 (2) | C4—C12 | 1.403 (3) |
Cu1—O1 | 1.955 (2) | C5—C6 | 1.340 (4) |
Cu1—O5i | 1.935 (2) | C5—H5 | 0.9300 |
Cu1—O1W | 2.323 (2) | C6—C7 | 1.432 (3) |
O1—C13 | 1.269 (3) | C6—H6 | 0.9300 |
O2—C13 | 1.229 (3) | C7—C8 | 1.404 (4) |
O5—C22 | 1.264 (3) | C7—C11 | 1.401 (3) |
O6—C22 | 1.231 (3) | C8—C9 | 1.356 (4) |
N1—C1 | 1.331 (3) | C8—H8 | 0.9300 |
N1—C12 | 1.349 (3) | C9—C10 | 1.391 (3) |
N2—C10 | 1.327 (3) | C9—H9 | 0.9300 |
N2—C11 | 1.357 (3) | C10—H10 | 0.9300 |
O3—C14 | 1.425 (3) | C11—C12 | 1.430 (3) |
O3—C15 | 1.376 (3) | C13—C14 | 1.524 (3) |
O4—C19 | 1.363 (3) | C14—H14A | 0.9700 |
O4—C21 | 1.423 (3) | C14—H14B | 0.9700 |
O5—Cu1ii | 1.935 (2) | C15—C16 | 1.389 (3) |
O1W—H1W1 | 0.85 (3) | C15—C20 | 1.380 (3) |
O1W—H1W2 | 0.85 (3) | C16—C17 | 1.381 (3) |
O2W—H2W1 | 0.85 (3) | C16—H16 | 0.9300 |
O2W—H2W2 | 0.85 (3) | C17—C18 | 1.373 (3) |
O3W—H3W1 | 0.85 (3) | C17—H17 | 0.9300 |
O3W—H3W2 | 0.85 (3) | C18—C19 | 1.389 (3) |
C1—C2 | 1.393 (4) | C18—H18 | 0.9300 |
C1—H1 | 0.9300 | C19—C20 | 1.386 (3) |
C2—C3 | 1.352 (4) | C20—H20 | 0.9300 |
C2—H2 | 0.9300 | C21—C22 | 1.519 (3) |
C3—C4 | 1.409 (4) | C21—H21A | 0.9700 |
C3—H3 | 0.9300 | C21—H21B | 0.9700 |
| | | |
N1—Cu1—N2 | 81.67 (7) | C5—C6—H6 | 119.1 |
N1—Cu1—O1W | 94.47 (6) | C6—C5—C4 | 121.3 (2) |
N2—Cu1—O1W | 100.24 (6) | C6—C5—H5 | 119.4 |
O1—Cu1—N1 | 172.78 (7) | C7—C6—H6 | 119.1 |
O1—Cu1—N2 | 91.22 (7) | C8—C7—C6 | 125.3 (2) |
O1—Cu1—O1W | 88.02 (6) | C9—C8—C7 | 120.1 (2) |
O5i—Cu1—N1 | 90.23 (7) | C9—C8—H8 | 120.0 |
O5i—Cu1—N2 | 162.71 (7) | C7—C8—H8 | 120.0 |
O5i—Cu1—O1 | 96.28 (7) | C7—C11—C12 | 120.1 (2) |
O5i—Cu1—O1W | 95.58 (7) | C8—C9—C10 | 119.8 (2) |
Cu1—O1W—H1W1 | 97 (2) | C8—C9—H9 | 120.1 |
Cu1—O1W—H1W2 | 93 (2) | C9—C10—H10 | 118.9 |
N1—C1—C2 | 122.5 (3) | C10—N2—Cu1 | 129.6 (2) |
N1—C1—H1 | 118.8 | C10—N2—C11 | 118.2 (2) |
N1—C12—C4 | 123.7 (2) | C10—C9—H9 | 120.1 |
N1—C12—C11 | 116.3 (2) | C11—N2—Cu1 | 112.1 (1) |
N2—C10—C9 | 122.2 (2) | C11—C7—C6 | 118.2 (2) |
N2—C10—H10 | 118.9 | C11—C7—C8 | 116.5 (2) |
N2—C11—C7 | 123.2 (2) | C12—N1—Cu1 | 113.0 (1) |
N2—C11—C12 | 116.7 (2) | C12—C4—C3 | 116.4 (2) |
O1—C13—C14 | 115.7 (2) | C12—C4—C5 | 118.6 (2) |
O2—C13—O1 | 126.0 (2) | C13—O1—Cu1 | 125.7 (1) |
O2—C13—C14 | 118.3 (2) | C13—C14—H14A | 108.7 |
O3—C14—C13 | 114.4 (2) | C13—C14—H14B | 108.7 |
O3—C14—H14A | 108.7 | C15—O3—C14 | 117.2 (2) |
O3—C14—H14B | 108.7 | C15—C16—H16 | 121.1 |
O3—C15—C20 | 115.0 (2) | C16—C17—H17 | 118.7 |
O3—C15—C16 | 124.4 (2) | C17—C16—C15 | 117.9 (2) |
O4—C19—C20 | 114.6 (2) | C17—C16—H16 | 121.1 |
O4—C19—C18 | 125.9 (2) | C17—C18—C19 | 119.0 (2) |
O4—C21—C22 | 114.3 (2) | C17—C18—H18 | 120.5 |
O4—C21—H21A | 108.7 | C18—C17—C16 | 122.5 (2) |
O4—C21—H21B | 108.7 | C18—C17—H17 | 118.7 |
O5—C22—C21 | 112.0 (2) | C19—O4—C21 | 118.5 (2) |
O6—C22—O5 | 126.2 (2) | C19—C18—H18 | 120.5 |
O6—C22—C21 | 121.7 (2) | C20—C15—C16 | 120.6 (2) |
C1—N1—Cu1 | 129.4 (2) | C20—C19—C18 | 119.5 (2) |
C1—N1—C12 | 117.6 (2) | C15—C20—C19 | 120.5 (2) |
C1—C2—H2 | 120.0 | C15—C20—H20 | 119.7 |
C2—C1—H1 | 118.8 | C19—C20—H20 | 119.7 |
C2—C3—C4 | 119.7 (2) | C22—O5—Cu1ii | 126.9 (2) |
C2—C3—H3 | 120.1 | C22—C21—H21A | 108.7 |
C3—C2—C1 | 120.0 (3) | C22—C21—H21B | 108.7 |
C3—C2—H2 | 120.0 | H1W1—O1W—H1W2 | 109 (2) |
C3—C4—C5 | 125.0 (2) | H2W1—O2W—H2W2 | 109 (2) |
C4—C3—H3 | 120.1 | H3W1—O3W—H3W2 | 109 (2) |
C4—C5—H5 | 119.4 | H14A—C14—H14B | 107.6 |
C4—C12—C11 | 120.0 (2) | H21A—C21—H21B | 107.6 |
C5—C6—C7 | 121.7 (2) | | |
| | | |
Cu1—N1—C1—C2 | −179.79 (18) | C1—C2—C3—C4 | −0.3 (4) |
Cu1—N1—C12—C4 | 178.02 (15) | C2—C3—C4—C5 | 178.2 (2) |
Cu1—N1—C12—C11 | −1.6 (2) | C2—C3—C4—C12 | −1.4 (3) |
Cu1—N2—C10—C9 | 176.56 (16) | C3—C4—C5—C6 | 179.3 (2) |
Cu1—N2—C11—C7 | −175.88 (15) | C3—C4—C12—N1 | 2.5 (3) |
Cu1—N2—C11—C12 | 4.9 (2) | C3—C4—C12—C11 | −177.94 (19) |
Cu1—O1—C13—O2 | 3.7 (3) | C4—C5—C6—C7 | −1.6 (4) |
Cu1—O1—C13—C14 | −173.36 (15) | C5—C4—C12—N1 | −177.09 (19) |
Cu1ii—O5—C22—O6 | −21.3 (3) | C5—C4—C12—C11 | 2.5 (3) |
Cu1ii—O5—C22—C21 | 159.77 (16) | C5—C6—C7—C8 | −176.9 (2) |
N1—Cu1—N2—C10 | 178.72 (19) | C5—C6—C7—C11 | 2.9 (3) |
N1—Cu1—N2—C11 | −4.40 (13) | C6—C7—C8—C9 | 179.0 (2) |
N1—C1—C2—C3 | 1.0 (4) | C6—C7—C11—N2 | 179.28 (19) |
N2—Cu1—N1—C1 | −177.0 (2) | C6—C7—C11—C12 | −1.5 (3) |
N2—Cu1—N1—C12 | 3.25 (13) | C7—C8—C9—C10 | 2.0 (4) |
N2—Cu1—O1—C13 | −113.74 (18) | C7—C11—C12—N1 | 178.47 (18) |
N2—C11—C12—N1 | −2.3 (3) | C7—C11—C12—C4 | −1.1 (3) |
N2—C11—C12—C4 | 178.11 (17) | C8—C7—C11—N2 | −0.9 (3) |
O5i—Cu1—N1—C1 | 18.38 (19) | C8—C7—C11—C12 | 178.30 (19) |
O5i—Cu1—N1—C12 | −161.42 (14) | C8—C9—C10—N2 | −1.5 (4) |
O5i—Cu1—N2—C10 | −118.4 (3) | C10—N2—C11—C7 | 1.4 (3) |
O5i—Cu1—N2—C11 | 58.4 (3) | C10—N2—C11—C12 | −177.84 (18) |
O5i—Cu1—O1—C13 | 50.65 (18) | C11—N2—C10—C9 | −0.2 (3) |
O1—Cu1—N2—C10 | −2.56 (18) | C11—C7—C8—C9 | −0.8 (3) |
O1—Cu1—N2—C11 | 174.31 (13) | C12—N1—C1—C2 | 0.0 (3) |
O1—C13—C14—O3 | −25.5 (3) | C12—C4—C5—C6 | −1.2 (3) |
O2—C13—C14—O3 | 157.2 (2) | C14—O3—C15—C16 | −3.1 (3) |
O3—C15—C16—C17 | 178.7 (2) | C14—O3—C15—C20 | 175.60 (19) |
O3—C15—C20—C19 | −179.02 (19) | C15—O3—C14—C13 | −71.6 (3) |
O4—C19—C20—C15 | −178.93 (19) | C15—C16—C17—C18 | −0.1 (4) |
O4—C21—C22—O5 | −177.85 (19) | C16—C15—C20—C19 | −0.3 (3) |
O4—C21—C22—O6 | 3.1 (3) | C16—C17—C18—C19 | 0.3 (4) |
O1W—Cu1—N1—C1 | −77.23 (19) | C17—C18—C19—O4 | 178.8 (2) |
O1W—Cu1—N1—C12 | 102.97 (14) | C17—C18—C19—C20 | −0.5 (3) |
O1W—Cu1—N2—C10 | 85.65 (18) | C18—C19—C20—C15 | 0.5 (3) |
O1W—Cu1—N2—C11 | −97.48 (13) | C19—O4—C21—C22 | 75.5 (3) |
O1W—Cu1—O1—C13 | 146.05 (18) | C20—C15—C16—C17 | 0.1 (3) |
C1—N1—C12—C4 | −1.8 (3) | C21—O4—C19—C18 | 0.2 (3) |
C1—N1—C12—C11 | 178.59 (18) | C21—O4—C19—C20 | 179.6 (2) |
Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) x+1/2, −y+3/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O3W | 0.85 (3) | 1.93 (3) | 2.775 (3) | 175 (3) |
O1W—H1W2···O6i | 0.85 (3) | 1.97 (3) | 2.781 (2) | 158 (3) |
O2W—H2W1···O2 | 0.85 (3) | 1.95 (3) | 2.774 (3) | 162 (3) |
O2W—H2W2···O6iii | 0.85 (3) | 2.04 (3) | 2.856 (2) | 161 (4) |
O3W—H3W1···O2Wiv | 0.85 (3) | 1.89 (3) | 2.726 (3) | 170 (3) |
O3W—H3W2···O1 | 0.85 (3) | 2.22 (2) | 2.928 (2) | 141 (3) |
O3W—H3W2···O3 | 0.85 (3) | 2.49 (2) | 3.249 (2) | 148 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) x−1/2, −y+3/2, z−1/2. |