metal-organic compounds
In the title complex, [Cu(C16H14N2O2)(C7H6N2)]·CH4O, [Cu(L)(1H-benzimidazole)]·CH3OH, [H2L = 3-methoxysalicylaldehyde (4-methoxybenzoyl)hydrazone, C16H16N2O4], the CuII atom is coordinated by two O atoms and one N atom of the fully deprotonated tridentate hydrazone ligand and one N atom from the 1H-benzimidazole molecule, thus defining a square planar coordination geometry. Adjacent molecules are linked by hydrogen bonds into a chain structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026169/rz6009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026169/rz6009Isup2.hkl |
CCDC reference: 255441
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.039
- wR factor = 0.089
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.65 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C H4 O
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 4912 Count of symmetry unique reflns 2637 Completeness (_total/calc) 186.27% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2275 Fraction of Friedel pairs measured 0.863 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion
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.
(1H-Benzimidazole-κN3)[3-methoxysalicylaldehyde
(4-methoxybenzoyl)hydrazonato-κ3O,N,O']copper(II)
methanol solvate top
Crystal data top
[Cu(C16H14N2O4)(C7H6N2)]·CH4O | F(000) = 530 |
Mr = 512.02 | Dx = 1.483 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 9816 reflections |
a = 13.534 (3) Å | θ = 3.0–27.5° |
b = 5.071 (1) Å | µ = 1.00 mm−1 |
c = 21.294 (6) Å | T = 293 K |
β = 128.31 (2)° | Prism, blue |
V = 1146.7 (6) Å3 | 0.38 × 0.25 × 0.18 mm |
Z = 2 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4912 independent reflections |
Radiation source: fine-focus sealed tube | 4199 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
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 = −6→6 |
Tmin = 0.703, Tmax = 0.841 | l = −27→27 |
10067 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0569P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4912 reflections | Δρmax = 0.45 e Å−3 |
316 parameters | Δρmin = −0.24 e Å−3 |
4 restraints | Absolute structure: Flack (1983), 2320 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.015 (11) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.50000 (3) | 0.46239 (6) | 0.50000 (2) | 0.04382 (11) | |
O1 | 0.5901 (2) | 0.5679 (4) | 0.61055 (13) | 0.0507 (5) | |
O2 | 0.9444 (2) | 0.5329 (5) | 0.98938 (14) | 0.0632 (6) | |
O3 | 0.4237 (2) | 0.3205 (5) | 0.39809 (12) | 0.0574 (6) | |
O4 | 0.2912 (3) | 0.2371 (6) | 0.24591 (14) | 0.0816 (9) | |
O5 | 0.9587 (2) | 0.0253 (6) | 0.69724 (16) | 0.0648 (7) | |
H26 | 0.886 (2) | 0.051 (10) | 0.684 (3) | 0.097* | |
N1 | 0.7213 (2) | 0.2296 (5) | 0.63356 (15) | 0.0464 (6) | |
N2 | 0.6375 (2) | 0.2171 (5) | 0.55025 (14) | 0.0442 (6) | |
N3 | 0.3608 (2) | 0.7152 (5) | 0.45009 (14) | 0.0451 (6) | |
N4 | 0.1715 (3) | 0.8663 (6) | 0.35051 (16) | 0.0549 (6) | |
H25 | 0.097 (2) | 0.892 (10) | 0.3013 (13) | 0.082* | |
C1 | 0.6848 (3) | 0.4195 (6) | 0.65776 (17) | 0.0430 (6) | |
C2 | 0.7565 (3) | 0.4535 (6) | 0.74521 (17) | 0.0433 (6) | |
C3 | 0.7241 (3) | 0.6572 (7) | 0.77350 (19) | 0.0527 (7) | |
H3 | 0.6602 | 0.7733 | 0.7370 | 0.063* | |
C4 | 0.7842 (3) | 0.6909 (7) | 0.85395 (19) | 0.0531 (8) | |
H4 | 0.7607 | 0.8277 | 0.8713 | 0.064* | |
C5 | 0.8796 (3) | 0.5206 (6) | 0.90877 (18) | 0.0485 (7) | |
C6 | 0.9135 (3) | 0.3187 (7) | 0.88201 (19) | 0.0522 (7) | |
H6 | 0.9781 | 0.2044 | 0.9188 | 0.063* | |
C7 | 0.8529 (3) | 0.2844 (6) | 0.80157 (18) | 0.0487 (7) | |
H7 | 0.8766 | 0.1465 | 0.7847 | 0.058* | |
C8 | 0.9165 (5) | 0.7434 (9) | 1.0201 (2) | 0.0784 (11) | |
H8A | 0.9382 | 0.9081 | 1.0093 | 0.118* | |
H8B | 0.9641 | 0.7223 | 1.0769 | 0.118* | |
H8C | 0.8282 | 0.7421 | 0.9950 | 0.118* | |
C9 | 0.6549 (3) | 0.0381 (7) | 0.5154 (2) | 0.0498 (8) | |
H9 | 0.7229 | −0.0751 | 0.5479 | 0.060* | |
C10 | 0.5784 (4) | −0.0026 (7) | 0.4306 (2) | 0.0481 (9) | |
C11 | 0.6164 (4) | −0.1959 (8) | 0.4016 (2) | 0.0676 (10) | |
H11 | 0.6893 | −0.2929 | 0.4374 | 0.081* | |
C12 | 0.5472 (4) | −0.2407 (10) | 0.3218 (3) | 0.0823 (12) | |
H12 | 0.5727 | −0.3676 | 0.3031 | 0.099* | |
C13 | 0.4377 (5) | −0.0959 (10) | 0.2682 (2) | 0.0796 (12) | |
H13 | 0.3916 | −0.1250 | 0.2135 | 0.096* | |
C14 | 0.3971 (3) | 0.0873 (8) | 0.2942 (2) | 0.0595 (9) | |
C15 | 0.4678 (3) | 0.1418 (7) | 0.37743 (18) | 0.0487 (7) | |
C16 | 0.2263 (5) | 0.2256 (14) | 0.1626 (3) | 0.111 (2) | |
H16A | 0.2835 | 0.2644 | 0.1515 | 0.167* | |
H16B | 0.1592 | 0.3526 | 0.1363 | 0.167* | |
H16C | 0.1920 | 0.0521 | 0.1434 | 0.167* | |
C17 | 0.2634 (3) | 0.6995 (7) | 0.37328 (19) | 0.0515 (8) | |
H17 | 0.2597 | 0.5819 | 0.3384 | 0.062* | |
C18 | 0.3279 (3) | 0.9157 (7) | 0.47966 (19) | 0.0420 (7) | |
C19 | 0.3970 (4) | 1.0273 (7) | 0.5551 (3) | 0.0488 (9) | |
H19 | 0.4772 | 0.9681 | 0.5970 | 0.059* | |
C20 | 0.3398 (4) | 1.2324 (7) | 0.5647 (2) | 0.0576 (8) | |
H20 | 0.3834 | 1.3145 | 0.6143 | 0.069* | |
C21 | 0.2193 (4) | 1.3192 (7) | 0.5025 (2) | 0.0600 (8) | |
H21 | 0.1837 | 1.4548 | 0.5120 | 0.072* | |
C22 | 0.1513 (3) | 1.2099 (7) | 0.4274 (2) | 0.0561 (8) | |
H22 | 0.0707 | 1.2679 | 0.3856 | 0.067* | |
C23 | 0.2097 (3) | 1.0083 (6) | 0.41763 (19) | 0.0470 (7) | |
C24 | 0.9599 (4) | −0.2476 (10) | 0.6869 (3) | 0.0867 (13) | |
H24A | 1.0441 | −0.3135 | 0.7249 | 0.130* | |
H24B | 0.9311 | −0.2828 | 0.6336 | 0.130* | |
H24C | 0.9053 | −0.3334 | 0.6949 | 0.130* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03522 (15) | 0.05301 (19) | 0.03199 (15) | 0.0032 (3) | 0.01524 (13) | −0.0004 (2) |
O1 | 0.0445 (12) | 0.0520 (13) | 0.0378 (11) | 0.0037 (10) | 0.0167 (10) | −0.0023 (10) |
O2 | 0.0613 (14) | 0.0805 (16) | 0.0369 (11) | −0.0002 (12) | 0.0251 (12) | −0.0042 (11) |
O3 | 0.0461 (12) | 0.0775 (17) | 0.0314 (10) | 0.0164 (12) | 0.0155 (10) | −0.0043 (10) |
O4 | 0.0695 (18) | 0.116 (2) | 0.0329 (12) | 0.0293 (17) | 0.0188 (13) | −0.0017 (13) |
O5 | 0.0379 (13) | 0.0781 (18) | 0.0526 (14) | 0.0004 (11) | 0.0152 (12) | −0.0061 (11) |
N1 | 0.0324 (13) | 0.0589 (16) | 0.0319 (12) | 0.0015 (11) | 0.0120 (11) | −0.0002 (11) |
N2 | 0.0329 (12) | 0.0559 (15) | 0.0329 (12) | −0.0015 (11) | 0.0150 (11) | −0.0028 (11) |
N3 | 0.0397 (13) | 0.0513 (14) | 0.0341 (13) | −0.0003 (11) | 0.0179 (12) | 0.0001 (10) |
N4 | 0.0390 (14) | 0.0643 (16) | 0.0382 (14) | 0.0077 (13) | 0.0123 (12) | 0.0011 (12) |
C1 | 0.0361 (15) | 0.0473 (16) | 0.0351 (14) | −0.0089 (13) | 0.0168 (13) | −0.0041 (12) |
C2 | 0.0384 (14) | 0.0460 (15) | 0.0359 (13) | −0.0091 (13) | 0.0182 (12) | −0.0023 (12) |
C3 | 0.0459 (17) | 0.0514 (18) | 0.0390 (16) | 0.0027 (15) | 0.0155 (14) | −0.0001 (13) |
C4 | 0.0549 (19) | 0.0533 (19) | 0.0436 (17) | −0.0022 (15) | 0.0267 (16) | −0.0100 (13) |
C5 | 0.0429 (15) | 0.0588 (18) | 0.0354 (13) | −0.0121 (14) | 0.0200 (13) | −0.0028 (13) |
C6 | 0.0443 (17) | 0.0598 (19) | 0.0403 (16) | 0.0060 (15) | 0.0201 (14) | 0.0070 (14) |
C7 | 0.0473 (17) | 0.0503 (17) | 0.0429 (16) | −0.0002 (14) | 0.0252 (14) | −0.0013 (13) |
C8 | 0.093 (3) | 0.086 (3) | 0.049 (2) | 0.000 (2) | 0.041 (2) | −0.0144 (18) |
C9 | 0.0375 (16) | 0.0564 (19) | 0.0457 (18) | 0.0063 (16) | 0.0209 (15) | 0.0019 (16) |
C10 | 0.045 (2) | 0.055 (2) | 0.0402 (18) | −0.0008 (15) | 0.0244 (17) | −0.0038 (13) |
C11 | 0.061 (2) | 0.076 (3) | 0.062 (2) | 0.0111 (19) | 0.036 (2) | −0.0080 (18) |
C12 | 0.080 (3) | 0.098 (3) | 0.067 (3) | 0.013 (3) | 0.045 (2) | −0.020 (2) |
C13 | 0.082 (3) | 0.100 (3) | 0.049 (2) | 0.012 (3) | 0.037 (2) | −0.016 (2) |
C14 | 0.0530 (19) | 0.076 (2) | 0.0401 (16) | 0.0026 (17) | 0.0243 (16) | −0.0056 (15) |
C15 | 0.0484 (17) | 0.0561 (17) | 0.0403 (15) | −0.0018 (15) | 0.0268 (14) | −0.0037 (13) |
C16 | 0.099 (4) | 0.157 (5) | 0.043 (2) | 0.036 (4) | 0.027 (3) | 0.007 (3) |
C17 | 0.0428 (17) | 0.0589 (19) | 0.0383 (15) | 0.0047 (14) | 0.0178 (14) | −0.0012 (13) |
C18 | 0.0404 (16) | 0.0460 (18) | 0.0375 (15) | 0.0003 (14) | 0.0232 (14) | 0.0045 (14) |
C19 | 0.045 (2) | 0.057 (2) | 0.0409 (18) | 0.0054 (16) | 0.0252 (17) | 0.0085 (15) |
C20 | 0.073 (2) | 0.0579 (19) | 0.0483 (18) | −0.0027 (18) | 0.0409 (19) | −0.0007 (15) |
C21 | 0.072 (2) | 0.056 (2) | 0.069 (2) | 0.0079 (18) | 0.052 (2) | 0.0042 (17) |
C22 | 0.0478 (18) | 0.0574 (19) | 0.0560 (19) | 0.0092 (15) | 0.0285 (17) | 0.0063 (15) |
C23 | 0.0387 (14) | 0.0535 (18) | 0.0440 (15) | 0.0005 (13) | 0.0232 (13) | 0.0017 (12) |
C24 | 0.062 (3) | 0.078 (3) | 0.088 (3) | 0.006 (2) | 0.030 (2) | −0.006 (2) |
Geometric parameters (Å, º) top
Cu1—N2 | 1.920 (3) | C8—H8A | 0.9600 |
Cu1—N3 | 1.960 (3) | C8—H8B | 0.9600 |
Cu1—O1 | 1.938 (2) | C8—H8C | 0.9600 |
Cu1—O3 | 1.875 (2) | C9—C10 | 1.435 (6) |
N1—C1 | 1.323 (4) | C9—H9 | 0.9300 |
N1—N2 | 1.394 (3) | C10—C11 | 1.414 (6) |
N2—C9 | 1.283 (5) | C10—C15 | 1.400 (5) |
O1—C1 | 1.274 (4) | C11—C12 | 1.357 (5) |
O3—C15 | 1.302 (4) | C11—H11 | 0.9300 |
N3—C17 | 1.322 (4) | C12—C13 | 1.393 (6) |
N3—C18 | 1.405 (4) | C12—H12 | 0.9300 |
N4—C17 | 1.323 (4) | C13—C14 | 1.359 (6) |
N4—C23 | 1.383 (4) | C13—H13 | 0.9300 |
N4—H25 | 0.91 (2) | C14—C15 | 1.426 (4) |
O2—C5 | 1.361 (4) | C16—H16A | 0.9600 |
O2—C8 | 1.421 (5) | C16—H16B | 0.9600 |
O4—C14 | 1.365 (5) | C16—H16C | 0.9600 |
O4—C16 | 1.411 (5) | C17—H17 | 0.9300 |
O5—C24 | 1.403 (6) | C18—C19 | 1.383 (6) |
O5—H26 | 0.85 (5) | C18—C23 | 1.381 (5) |
C1—C2 | 1.483 (4) | C19—C20 | 1.385 (5) |
C2—C7 | 1.392 (4) | C19—H19 | 0.9300 |
C2—C3 | 1.396 (5) | C20—C21 | 1.389 (5) |
C3—C4 | 1.378 (4) | C20—H20 | 0.9300 |
C3—H3 | 0.9300 | C21—C22 | 1.374 (5) |
C4—C5 | 1.381 (5) | C21—H21 | 0.9300 |
C4—H4 | 0.9300 | C22—C23 | 1.385 (5) |
C5—C6 | 1.381 (5) | C22—H22 | 0.9300 |
C6—C7 | 1.377 (4) | C24—H24A | 0.9600 |
C6—H6 | 0.9300 | C24—H24B | 0.9600 |
C7—H7 | 0.9300 | C24—H24C | 0.9600 |
N2—Cu1—N3 | 179.2 (1) | C10—C9—H9 | 117.2 |
N2—Cu1—O1 | 80.8 (1) | C10—C11—H11 | 119.8 |
O1—Cu1—N3 | 98.5 (1) | C10—C15—C14 | 117.4 (3) |
O3—Cu1—N2 | 92.5 (1) | C11—C10—C9 | 118.4 (4) |
O3—Cu1—N3 | 88.2 (1) | C11—C12—C13 | 119.8 (4) |
O3—Cu1—O1 | 172.9 (1) | C11—C12—H12 | 120.1 |
N1—N2—Cu1 | 115.0 (2) | C12—C11—C10 | 120.5 (4) |
N1—C1—C2 | 117.5 (3) | C12—C11—H11 | 119.8 |
N2—C9—C10 | 125.6 (3) | C12—C13—H13 | 119.4 |
N2—C9—H9 | 117.2 | C13—C12—H12 | 120.1 |
N3—C17—N4 | 113.9 (3) | C13—C14—O4 | 125.1 (3) |
N3—C17—H17 | 123.0 | C13—C14—C15 | 120.7 (4) |
N4—C17—H17 | 123.0 | C14—O4—C16 | 117.9 (3) |
N4—C23—C22 | 131.1 (3) | C14—C13—C12 | 121.3 (4) |
O1—C1—N1 | 123.9 (3) | C14—C13—H13 | 119.4 |
O1—C1—C2 | 118.5 (3) | C15—O3—Cu1 | 128.3 (2) |
O2—C5—C4 | 124.9 (3) | C15—C10—C11 | 120.4 (4) |
O2—C5—C6 | 115.8 (3) | C15—C10—C9 | 121.2 (4) |
O2—C8—H8A | 109.5 | C17—N3—Cu1 | 121.2 (2) |
O2—C8—H8B | 109.5 | C17—N3—C18 | 104.4 (3) |
O2—C8—H8C | 109.5 | C17—N4—C23 | 106.9 (3) |
O3—C15—C10 | 125.1 (3) | C17—N4—H25 | 129 (3) |
O3—C15—C14 | 117.4 (3) | C18—N3—Cu1 | 134.0 (2) |
O4—C14—C15 | 114.2 (3) | C18—C19—C20 | 116.2 (4) |
O4—C16—H16A | 109.5 | C18—C19—H19 | 121.9 |
O4—C16—H16B | 109.5 | C18—C23—N4 | 106.3 (3) |
O4—C16—H16C | 109.5 | C18—C23—C22 | 122.6 (3) |
O5—C24—H24A | 109.5 | C19—C18—N3 | 130.0 (3) |
O5—C24—H24B | 109.5 | C19—C20—C21 | 122.0 (4) |
O5—C24—H24C | 109.5 | C19—C20—H20 | 119.0 |
C1—N1—N2 | 108.9 (2) | C20—C19—H19 | 121.9 |
C1—O1—Cu1 | 111.3 (2) | C20—C21—H21 | 119.2 |
C2—C3—H3 | 119.1 | C21—C20—H20 | 119.0 |
C2—C7—H7 | 119.6 | C21—C22—C23 | 116.1 (3) |
C3—C2—C1 | 119.5 (3) | C21—C22—H22 | 121.9 |
C3—C4—C5 | 119.7 (3) | C22—C21—C20 | 121.7 (3) |
C3—C4—H4 | 120.1 | C22—C21—H21 | 119.2 |
C4—C3—C2 | 121.8 (3) | C23—N4—H25 | 124 (3) |
C4—C3—H3 | 119.1 | C23—C18—N3 | 108.6 (3) |
C4—C5—C6 | 119.4 (3) | C23—C18—C19 | 121.3 (3) |
C5—O2—C8 | 117.9 (3) | C23—C22—H22 | 121.9 |
C5—C4—H4 | 120.1 | C24—O5—H26 | 103 (4) |
C5—C6—H6 | 119.6 | H8A—C8—H8B | 109.5 |
C6—C7—C2 | 120.8 (3) | H8A—C8—H8C | 109.5 |
C6—C7—H7 | 119.6 | H8B—C8—H8C | 109.5 |
C7—C2—C1 | 123.0 (3) | H16A—C16—H16B | 109.5 |
C7—C2—C3 | 117.5 (3) | H16A—C16—H16C | 109.5 |
C7—C6—C5 | 120.9 (3) | H16B—C16—H16C | 109.5 |
C7—C6—H6 | 119.6 | H24A—C24—H24B | 109.5 |
C9—N2—Cu1 | 126.7 (2) | H24A—C24—H24C | 109.5 |
C9—N2—N1 | 118.2 (3) | H24B—C24—H24C | 109.5 |
Cu1—N2—C9—C10 | 4.4 (5) | C1—C2—C7—C6 | −177.6 (3) |
Cu1—N3—C17—N4 | 173.3 (2) | C2—C3—C4—C5 | 0.3 (5) |
Cu1—N3—C18—C19 | 11.7 (6) | C3—C2—C7—C6 | −0.1 (5) |
Cu1—N3—C18—C23 | −171.9 (2) | C3—C4—C5—O2 | −179.2 (3) |
Cu1—O1—C1—N1 | 4.3 (4) | C3—C4—C5—C6 | 0.1 (5) |
Cu1—O1—C1—C2 | −173.4 (2) | C4—C5—C6—C7 | −0.4 (5) |
Cu1—O3—C15—C10 | 7.2 (5) | C5—C6—C7—C2 | 0.4 (5) |
Cu1—O3—C15—C14 | −173.3 (3) | C7—C2—C3—C4 | −0.3 (5) |
N1—N2—C9—C10 | −179.8 (4) | C8—O2—C5—C4 | −3.2 (5) |
N1—C1—C2—C3 | 177.8 (3) | C8—O2—C5—C6 | 177.6 (3) |
N1—C1—C2—C7 | −4.8 (4) | C9—C10—C11—C12 | −179.8 (4) |
N2—Cu1—O1—C1 | −3.7 (2) | C9—C10—C15—O3 | −0.2 (6) |
N2—Cu1—O3—C15 | −6.9 (3) | C9—C10—C15—C14 | −179.6 (4) |
N2—N1—C1—O1 | −1.9 (4) | C10—C11—C12—C13 | −0.2 (7) |
N2—N1—C1—C2 | 175.8 (2) | C11—C10—C15—O3 | 178.9 (4) |
N2—C9—C10—C15 | −5.9 (6) | C11—C10—C15—C14 | −0.5 (6) |
N2—C9—C10—C11 | 175.0 (4) | C11—C12—C13—C14 | −1.2 (8) |
N3—Cu1—O1—C1 | 176.4 (2) | C12—C13—C14—O4 | −179.9 (4) |
N3—Cu1—O3—C15 | 173.0 (3) | C12—C13—C14—C15 | 1.8 (7) |
N3—C18—C19—C20 | 177.1 (3) | C13—C14—C15—O3 | 179.6 (4) |
N3—C18—C23—N4 | −0.6 (4) | C13—C14—C15—C10 | −0.9 (6) |
N3—C18—C23—C22 | −179.1 (3) | C15—C10—C11—C12 | 1.1 (7) |
O1—Cu1—N2—N1 | 2.9 (2) | C16—O4—C14—C13 | −8.0 (7) |
O1—Cu1—N2—C9 | 178.7 (3) | C16—O4—C14—C15 | 170.4 (4) |
O1—Cu1—N3—C17 | −171.8 (3) | C17—N3—C18—C19 | −175.8 (4) |
O1—Cu1—N3—C18 | −0.3 (3) | C17—N3—C18—C23 | 0.6 (4) |
O1—C1—C2—C3 | −4.3 (4) | C17—N4—C23—C18 | 0.3 (4) |
O1—C1—C2—C7 | 173.1 (3) | C17—N4—C23—C22 | 178.7 (3) |
O2—C5—C6—C7 | 178.9 (3) | C18—N3—C17—N4 | −0.4 (4) |
O3—Cu1—N2—N1 | −174.7 (2) | C18—C19—C20—C21 | 0.8 (5) |
O3—Cu1—N2—C9 | 1.2 (3) | C19—C20—C21—C22 | −1.5 (5) |
O3—Cu1—N3—C17 | 5.8 (3) | C19—C18—C23—N4 | 176.2 (3) |
O3—Cu1—N3—C18 | 177.3 (3) | C19—C18—C23—C22 | −2.4 (5) |
O4—C14—C15—O3 | 1.2 (5) | C20—C21—C22—C23 | 0.3 (5) |
O4—C14—C15—C10 | −179.4 (3) | C21—C22—C23—N4 | −176.5 (3) |
C1—N1—N2—Cu1 | −1.5 (3) | C21—C22—C23—C18 | 1.6 (5) |
C1—N1—N2—C9 | −177.8 (3) | C23—N4—C17—N3 | 0.1 (4) |
C1—C2—C3—C4 | 177.3 (3) | C23—C18—C19—C20 | 1.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H25···O5i | 0.91 (2) | 1.86 (2) | 2.756 (4) | 171 (4) |
O5—H26···N1 | 0.85 (5) | 1.99 (5) | 2.800 (4) | 158 (5) |
Symmetry code: (i) x−1, −y+1, z−1/2. |