In the title compound, [Cu
2(C
4H
4O
4)
2(C
11H
10N
4O)]
n, mono-periodic coordination polymer ribbons are held into the crystal structure by means of N—H
O hydrogen bonding and crystal packing forces.
Supporting information
CCDC reference: 2290886
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.009 Å
- R factor = 0.056
- wR factor = 0.151
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00886 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C2 ..O3 . 99.60 Degree
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C19 ..O4 . 98.40 Degree
PLAT601_ALERT_2_C Unit Cell Contains Solvent Accessible VOIDS of . 35 Ang 3
PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on Cu2 1.26 eA-3
PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on Cu1 1.11 eA-3
Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension 1 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report
PLAT480_ALERT_4_G Long H...A H-Bond Reported H9 ..O5 . 2.74 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H19 ..O4 . 2.84 Ang.
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1 (II) . 2.09 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Cu2 (II) . 2.10 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 2 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 4.2 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
9 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
4 ALERT type 5 Informative message, check
Data collection: COSMO (Bruker, 2009); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: CrystalMakerX (Palmer, 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Poly[[µ-1,3-bis(pyridin-3-yl)urea]bis(µ
4-succinato)dicopper(II)]
top
Crystal data top
[Cu2(C4H4O4)2(C11H10N4O)] | F(000) = 1160 |
Mr = 573.45 | Dx = 1.857 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.587 (2) Å | Cell parameters from 2446 reflections |
b = 6.7579 (10) Å | θ = 2.8–25.1° |
c = 20.942 (3) Å | µ = 2.14 mm−1 |
β = 111.614 (2)° | T = 173 K |
V = 2050.9 (5) Å3 | Plate, green |
Z = 4 | 0.24 × 0.12 × 0.05 mm |
Data collection top
Bruker APEXII CCD diffractometer | 3758 independent reflections |
Radiation source: sealed tube | 2378 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.110 |
Detector resolution: 8.36 pixels mm-1 | θmax = 25.4°, θmin = 1.4° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −8→8 |
Tmin = 0.568, Tmax = 0.745 | l = −25→25 |
15941 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0685P)2] where P = (Fo2 + 2Fc2)/3 |
3758 reflections | (Δ/σ)max = 0.001 |
307 parameters | Δρmax = 1.12 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
Special details top
Experimental. Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K. A suitable crystal was chosen and mounted on a nylon loop using
Paratone oil. Data were measured using omega scans of 0.5° per frame
for 30 s. The total number of images were based on
results from the program COSMO where redundancy was expected to be 4 and
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which
corrects for Lp. Scaling and absorption corrections were applied using SADABS6
multi-scan technique, supplied by George Sheldrick. The structure was solved
by the direct method using the SHELXT program and refined by least squares
method on F2, SHELXL, incorporated in OLEX2. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.76095 (5) | 0.56430 (10) | 0.20555 (4) | 0.0199 (2) | |
Cu2 | 0.77124 (5) | 0.49295 (10) | 0.33295 (4) | 0.0198 (2) | |
O1 | 0.6695 (3) | 0.6855 (6) | 0.3154 (2) | 0.0241 (10) | |
O2 | 0.6730 (3) | 0.7626 (6) | 0.2124 (2) | 0.0257 (11) | |
O3 | 0.6784 (3) | 1.2834 (6) | 0.2892 (2) | 0.0250 (10) | |
O4 | 0.6616 (3) | 1.3542 (6) | 0.1809 (2) | 0.0228 (10) | |
O5 | 0.8617 (3) | 0.7122 (6) | 0.3540 (2) | 0.0272 (11) | |
O6 | 0.8587 (3) | 0.7601 (6) | 0.2474 (2) | 0.0269 (11) | |
O7 | 0.8683 (3) | 1.3085 (6) | 0.3309 (2) | 0.0284 (11) | |
O8 | 0.8527 (3) | 1.3529 (6) | 0.2213 (2) | 0.0232 (10) | |
O9 | 0.5334 (3) | 0.3287 (7) | 0.4400 (2) | 0.0355 (12) | |
N1 | 0.7897 (3) | 0.4419 (7) | 0.4394 (3) | 0.0190 (12) | |
N2 | 0.6521 (4) | 0.3177 (7) | 0.5442 (3) | 0.0226 (12) | |
H2 | 0.665061 | 0.298117 | 0.588321 | 0.027* | |
N3 | 0.5065 (4) | 0.2208 (7) | 0.5341 (3) | 0.0225 (12) | |
H3 | 0.533315 | 0.195629 | 0.578293 | 0.027* | |
N4 | 0.2765 (4) | 0.1280 (7) | 0.4043 (2) | 0.0207 (12) | |
C1 | 0.6429 (4) | 0.7848 (8) | 0.2603 (3) | 0.0196 (14) | |
C2 | 0.5697 (4) | 0.9394 (8) | 0.2500 (3) | 0.0194 (14) | |
H2A | 0.579259 | 1.002925 | 0.294759 | 0.023* | |
H2B | 0.508546 | 0.874023 | 0.234080 | 0.023* | |
C3 | 0.5692 (4) | 1.0992 (9) | 0.1984 (3) | 0.0190 (14) | |
H3A | 0.576689 | 1.034695 | 0.158311 | 0.023* | |
H3B | 0.508195 | 1.165147 | 0.181940 | 0.023* | |
C4 | 0.6433 (4) | 1.2555 (8) | 0.2259 (3) | 0.0181 (14) | |
C5 | 0.8876 (4) | 0.7960 (9) | 0.3111 (3) | 0.0197 (14) | |
C6 | 0.9644 (4) | 0.9500 (8) | 0.3372 (3) | 0.0225 (15) | |
H6A | 0.961873 | 1.010462 | 0.379568 | 0.027* | |
H6B | 1.024551 | 0.881653 | 0.349782 | 0.027* | |
C7 | 0.9604 (4) | 1.1147 (9) | 0.2866 (3) | 0.0240 (15) | |
H7A | 1.021401 | 1.180573 | 0.301650 | 0.029* | |
H7B | 0.948973 | 1.054800 | 0.241052 | 0.029* | |
C8 | 0.8870 (4) | 1.2704 (9) | 0.2789 (3) | 0.0213 (15) | |
C9 | 0.8712 (5) | 0.4774 (9) | 0.4890 (3) | 0.0280 (16) | |
H9 | 0.922054 | 0.513711 | 0.476843 | 0.034* | |
C10 | 0.8834 (5) | 0.4625 (9) | 0.5578 (3) | 0.0279 (16) | |
H10 | 0.942091 | 0.487920 | 0.592295 | 0.034* | |
C11 | 0.8108 (4) | 0.4111 (9) | 0.5757 (3) | 0.0250 (15) | |
H11 | 0.818417 | 0.401257 | 0.622687 | 0.030* | |
C12 | 0.7253 (4) | 0.3733 (8) | 0.5245 (3) | 0.0213 (14) | |
C13 | 0.7181 (5) | 0.3899 (9) | 0.4566 (3) | 0.0234 (15) | |
H13 | 0.660291 | 0.363379 | 0.421060 | 0.028* | |
C14 | 0.5621 (5) | 0.2911 (9) | 0.5012 (3) | 0.0235 (15) | |
C15 | 0.2276 (5) | 0.0979 (9) | 0.4441 (4) | 0.0260 (16) | |
H15 | 0.163956 | 0.066116 | 0.423285 | 0.031* | |
C16 | 0.2677 (5) | 0.1121 (8) | 0.5150 (3) | 0.0253 (15) | |
H16 | 0.231447 | 0.093317 | 0.542417 | 0.030* | |
C17 | 0.3608 (4) | 0.1539 (9) | 0.5456 (3) | 0.0249 (15) | |
H17 | 0.389672 | 0.160856 | 0.594176 | 0.030* | |
C18 | 0.4114 (4) | 0.1852 (8) | 0.5044 (3) | 0.0188 (14) | |
C19 | 0.3656 (5) | 0.1700 (9) | 0.4340 (3) | 0.0251 (15) | |
H19 | 0.399984 | 0.190872 | 0.405368 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0226 (5) | 0.0173 (4) | 0.0204 (4) | 0.0010 (3) | 0.0088 (4) | 0.0007 (3) |
Cu2 | 0.0227 (5) | 0.0170 (4) | 0.0207 (4) | 0.0002 (3) | 0.0092 (4) | 0.0002 (3) |
O1 | 0.030 (3) | 0.021 (2) | 0.025 (3) | 0.0066 (19) | 0.015 (2) | 0.0068 (19) |
O2 | 0.034 (3) | 0.021 (2) | 0.025 (3) | 0.009 (2) | 0.015 (2) | 0.0029 (19) |
O3 | 0.031 (3) | 0.023 (2) | 0.022 (3) | −0.007 (2) | 0.010 (2) | −0.0049 (19) |
O4 | 0.026 (3) | 0.024 (2) | 0.018 (2) | −0.0066 (19) | 0.008 (2) | 0.0026 (19) |
O5 | 0.032 (3) | 0.022 (2) | 0.025 (3) | −0.012 (2) | 0.007 (2) | 0.001 (2) |
O6 | 0.032 (3) | 0.024 (3) | 0.028 (3) | −0.006 (2) | 0.015 (2) | −0.006 (2) |
O7 | 0.029 (3) | 0.026 (3) | 0.032 (3) | 0.012 (2) | 0.012 (2) | 0.003 (2) |
O8 | 0.025 (3) | 0.022 (2) | 0.021 (2) | 0.0053 (19) | 0.007 (2) | 0.0023 (19) |
O9 | 0.028 (3) | 0.049 (3) | 0.027 (3) | −0.003 (2) | 0.006 (2) | 0.013 (2) |
N1 | 0.019 (3) | 0.015 (3) | 0.019 (3) | 0.002 (2) | 0.004 (2) | 0.002 (2) |
N2 | 0.029 (3) | 0.019 (3) | 0.024 (3) | 0.001 (2) | 0.015 (3) | 0.004 (2) |
N3 | 0.029 (3) | 0.017 (3) | 0.021 (3) | 0.001 (2) | 0.009 (3) | 0.005 (2) |
N4 | 0.028 (3) | 0.015 (3) | 0.019 (3) | −0.002 (2) | 0.008 (3) | 0.001 (2) |
C1 | 0.024 (4) | 0.012 (3) | 0.025 (4) | −0.009 (3) | 0.012 (3) | −0.006 (3) |
C2 | 0.018 (3) | 0.018 (3) | 0.024 (3) | −0.002 (3) | 0.010 (3) | 0.004 (3) |
C3 | 0.018 (3) | 0.020 (3) | 0.021 (3) | −0.001 (3) | 0.009 (3) | −0.002 (3) |
C4 | 0.016 (3) | 0.010 (3) | 0.026 (4) | 0.005 (2) | 0.005 (3) | −0.002 (3) |
C5 | 0.013 (3) | 0.020 (3) | 0.024 (4) | 0.005 (3) | 0.003 (3) | 0.005 (3) |
C6 | 0.017 (4) | 0.020 (4) | 0.028 (4) | −0.004 (3) | 0.005 (3) | −0.003 (3) |
C7 | 0.021 (4) | 0.023 (4) | 0.028 (4) | 0.001 (3) | 0.009 (3) | −0.002 (3) |
C8 | 0.021 (4) | 0.016 (3) | 0.032 (4) | −0.007 (3) | 0.014 (3) | −0.004 (3) |
C9 | 0.023 (4) | 0.036 (4) | 0.028 (4) | −0.001 (3) | 0.013 (3) | 0.001 (3) |
C10 | 0.024 (4) | 0.029 (4) | 0.021 (4) | −0.001 (3) | −0.002 (3) | 0.008 (3) |
C11 | 0.032 (4) | 0.026 (4) | 0.017 (3) | 0.006 (3) | 0.009 (3) | 0.000 (3) |
C12 | 0.028 (4) | 0.012 (3) | 0.027 (4) | −0.001 (3) | 0.014 (3) | 0.001 (3) |
C13 | 0.031 (4) | 0.021 (4) | 0.019 (3) | 0.002 (3) | 0.011 (3) | −0.001 (3) |
C14 | 0.027 (4) | 0.017 (3) | 0.029 (4) | 0.003 (3) | 0.012 (3) | 0.002 (3) |
C15 | 0.019 (4) | 0.019 (4) | 0.040 (4) | 0.002 (3) | 0.011 (3) | −0.003 (3) |
C16 | 0.038 (4) | 0.014 (3) | 0.033 (4) | −0.001 (3) | 0.024 (4) | 0.005 (3) |
C17 | 0.026 (4) | 0.026 (4) | 0.024 (4) | 0.001 (3) | 0.011 (3) | −0.002 (3) |
C18 | 0.024 (4) | 0.015 (3) | 0.018 (3) | 0.000 (3) | 0.008 (3) | 0.001 (3) |
C19 | 0.029 (4) | 0.021 (4) | 0.027 (4) | 0.001 (3) | 0.013 (3) | −0.001 (3) |
Geometric parameters (Å, º) top
Cu1—O2 | 1.960 (4) | C2—H2A | 0.9900 |
Cu1—O4i | 2.023 (4) | C2—H2B | 0.9900 |
Cu1—O6 | 1.963 (4) | C2—C3 | 1.526 (8) |
Cu1—O8i | 1.961 (4) | C3—H3A | 0.9900 |
Cu1—N4ii | 2.197 (5) | C3—H3B | 0.9900 |
Cu2—O1 | 1.979 (4) | C3—C4 | 1.515 (8) |
Cu2—O3i | 1.990 (4) | C5—C6 | 1.528 (8) |
Cu2—O5 | 1.980 (4) | C6—H6A | 0.9900 |
Cu2—O7i | 1.973 (4) | C6—H6B | 0.9900 |
Cu2—N1 | 2.167 (5) | C6—C7 | 1.522 (8) |
O1—C1 | 1.265 (7) | C7—H7A | 0.9900 |
O2—C1 | 1.264 (7) | C7—H7B | 0.9900 |
O3—C4 | 1.248 (7) | C7—C8 | 1.519 (8) |
O4—C4 | 1.271 (7) | C9—H9 | 0.9500 |
O5—C5 | 1.249 (7) | C9—C10 | 1.386 (9) |
O6—C5 | 1.263 (7) | C10—H10 | 0.9500 |
O7—C8 | 1.254 (7) | C10—C11 | 1.361 (9) |
O8—C8 | 1.256 (7) | C11—H11 | 0.9500 |
O9—C14 | 1.218 (7) | C11—C12 | 1.392 (8) |
N1—C9 | 1.333 (8) | C12—C13 | 1.389 (8) |
N1—C13 | 1.340 (7) | C13—H13 | 0.9500 |
N2—H2 | 0.8800 | C15—H15 | 0.9500 |
N2—C12 | 1.401 (8) | C15—C16 | 1.387 (9) |
N2—C14 | 1.371 (8) | C16—H16 | 0.9500 |
N3—H3 | 0.8800 | C16—C17 | 1.383 (9) |
N3—C14 | 1.376 (8) | C17—H17 | 0.9500 |
N3—C18 | 1.400 (8) | C17—C18 | 1.383 (8) |
N4—C15 | 1.335 (8) | C18—C19 | 1.385 (8) |
N4—C19 | 1.327 (8) | C19—H19 | 0.9500 |
C1—C2 | 1.504 (8) | | |
| | | |
O2—Cu1—O4i | 90.48 (18) | O3—C4—O4 | 125.4 (5) |
O2—Cu1—O6 | 87.41 (18) | O3—C4—C3 | 119.0 (5) |
O2—Cu1—O8i | 166.45 (17) | O4—C4—C3 | 115.5 (5) |
O2—Cu1—N4ii | 91.11 (18) | O5—C5—O6 | 126.1 (6) |
O4i—Cu1—N4ii | 89.25 (17) | O5—C5—C6 | 117.9 (6) |
O6—Cu1—O4i | 169.11 (17) | O6—C5—C6 | 115.9 (5) |
O6—Cu1—N4ii | 101.47 (18) | C5—C6—H6A | 108.5 |
O8i—Cu1—O4i | 88.52 (17) | C5—C6—H6B | 108.5 |
O8i—Cu1—O6 | 91.03 (18) | H6A—C6—H6B | 107.5 |
O8i—Cu1—N4ii | 102.38 (18) | C7—C6—C5 | 115.0 (5) |
O1—Cu2—O3i | 89.16 (18) | C7—C6—H6A | 108.5 |
O1—Cu2—O5 | 90.34 (18) | C7—C6—H6B | 108.5 |
O1—Cu2—N1 | 95.10 (17) | C6—C7—H7A | 108.6 |
O3i—Cu2—N1 | 99.11 (18) | C6—C7—H7B | 108.6 |
O5—Cu2—O3i | 166.52 (17) | H7A—C7—H7B | 107.6 |
O5—Cu2—N1 | 94.36 (18) | C8—C7—C6 | 114.6 (5) |
O7i—Cu2—O1 | 168.62 (18) | C8—C7—H7A | 108.6 |
O7i—Cu2—O3i | 88.50 (18) | C8—C7—H7B | 108.6 |
O7i—Cu2—O5 | 89.35 (19) | O7—C8—O8 | 126.2 (6) |
O7i—Cu2—N1 | 96.27 (18) | O7—C8—C7 | 117.2 (6) |
C1—O1—Cu2 | 119.2 (4) | O8—C8—C7 | 116.6 (5) |
C1—O2—Cu1 | 127.8 (4) | N1—C9—H9 | 119.2 |
C4—O3—Cu2iii | 123.8 (4) | N1—C9—C10 | 121.6 (6) |
C4—O4—Cu1iii | 122.6 (4) | C10—C9—H9 | 119.2 |
C5—O5—Cu2 | 124.8 (4) | C9—C10—H10 | 120.2 |
C5—O6—Cu1 | 121.1 (4) | C11—C10—C9 | 119.7 (6) |
C8—O7—Cu2iii | 125.0 (4) | C11—C10—H10 | 120.2 |
C8—O8—Cu1iii | 120.7 (4) | C10—C11—H11 | 120.3 |
C9—N1—Cu2 | 120.0 (4) | C10—C11—C12 | 119.5 (6) |
C9—N1—C13 | 119.1 (5) | C12—C11—H11 | 120.3 |
C13—N1—Cu2 | 120.7 (4) | C11—C12—N2 | 118.4 (6) |
C12—N2—H2 | 116.9 | C13—C12—N2 | 123.7 (6) |
C14—N2—H2 | 116.9 | C13—C12—C11 | 117.9 (6) |
C14—N2—C12 | 126.1 (5) | N1—C13—C12 | 122.3 (6) |
C14—N3—H3 | 116.7 | N1—C13—H13 | 118.8 |
C14—N3—C18 | 126.5 (5) | C12—C13—H13 | 118.8 |
C18—N3—H3 | 116.7 | O9—C14—N2 | 123.6 (6) |
C15—N4—Cu1iv | 129.1 (4) | O9—C14—N3 | 122.9 (6) |
C19—N4—Cu1iv | 111.2 (4) | N2—C14—N3 | 113.4 (6) |
C19—N4—C15 | 118.6 (6) | N4—C15—H15 | 119.2 |
O1—C1—C2 | 118.4 (5) | N4—C15—C16 | 121.5 (6) |
O2—C1—O1 | 124.7 (6) | C16—C15—H15 | 119.2 |
O2—C1—C2 | 116.9 (5) | C15—C16—H16 | 120.3 |
C1—C2—H2A | 108.9 | C17—C16—C15 | 119.4 (6) |
C1—C2—H2B | 108.9 | C17—C16—H16 | 120.3 |
C1—C2—C3 | 113.5 (5) | C16—C17—H17 | 120.5 |
H2A—C2—H2B | 107.7 | C18—C17—C16 | 119.0 (6) |
C3—C2—H2A | 108.9 | C18—C17—H17 | 120.5 |
C3—C2—H2B | 108.9 | C17—C18—N3 | 120.1 (6) |
C2—C3—H3A | 108.6 | C17—C18—C19 | 117.7 (6) |
C2—C3—H3B | 108.6 | C19—C18—N3 | 122.1 (6) |
H3A—C3—H3B | 107.5 | N4—C19—C18 | 123.7 (6) |
C4—C3—C2 | 114.8 (5) | N4—C19—H19 | 118.2 |
C4—C3—H3A | 108.6 | C18—C19—H19 | 118.2 |
C4—C3—H3B | 108.6 | | |
| | | |
Cu1—O2—C1—O1 | 4.2 (9) | N4—C15—C16—C17 | −1.5 (9) |
Cu1—O2—C1—C2 | −175.2 (4) | C1—C2—C3—C4 | −78.3 (7) |
Cu1iii—O4—C4—O3 | 5.2 (8) | C2—C3—C4—O3 | −22.2 (8) |
Cu1iii—O4—C4—C3 | −177.9 (4) | C2—C3—C4—O4 | 160.7 (5) |
Cu1—O6—C5—O5 | 2.4 (9) | C5—C6—C7—C8 | 75.8 (7) |
Cu1—O6—C5—C6 | 179.4 (4) | C6—C7—C8—O7 | 32.4 (8) |
Cu1iii—O8—C8—O7 | 0.4 (9) | C6—C7—C8—O8 | −149.6 (5) |
Cu1iii—O8—C8—C7 | −177.5 (4) | C9—N1—C13—C12 | 0.7 (9) |
Cu1iv—N4—C15—C16 | 167.8 (4) | C9—C10—C11—C12 | 0.3 (9) |
Cu1iv—N4—C19—C18 | −169.4 (5) | C10—C11—C12—N2 | 179.0 (6) |
Cu2—O1—C1—O2 | 4.5 (8) | C10—C11—C12—C13 | 0.0 (9) |
Cu2—O1—C1—C2 | −176.2 (4) | C11—C12—C13—N1 | −0.5 (9) |
Cu2iii—O3—C4—O4 | 0.4 (8) | C12—N2—C14—O9 | −6.2 (9) |
Cu2iii—O3—C4—C3 | −176.4 (4) | C12—N2—C14—N3 | 175.0 (5) |
Cu2—O5—C5—O6 | 2.4 (9) | C13—N1—C9—C10 | −0.3 (9) |
Cu2—O5—C5—C6 | −174.6 (4) | C14—N2—C12—C11 | 174.2 (5) |
Cu2iii—O7—C8—O8 | 5.8 (9) | C14—N2—C12—C13 | −6.8 (9) |
Cu2iii—O7—C8—C7 | −176.4 (4) | C14—N3—C18—C17 | −166.6 (6) |
Cu2—N1—C9—C10 | 174.5 (5) | C14—N3—C18—C19 | 16.7 (9) |
Cu2—N1—C13—C12 | −174.1 (4) | C15—N4—C19—C18 | −0.2 (9) |
O1—C1—C2—C3 | 157.7 (5) | C15—C16—C17—C18 | 1.6 (9) |
O2—C1—C2—C3 | −22.9 (8) | C16—C17—C18—N3 | −177.7 (5) |
O5—C5—C6—C7 | −150.1 (6) | C16—C17—C18—C19 | −0.9 (9) |
O6—C5—C6—C7 | 32.6 (8) | C17—C18—C19—N4 | 0.3 (9) |
N1—C9—C10—C11 | −0.2 (10) | C18—N3—C14—O9 | −1.0 (10) |
N2—C12—C13—N1 | −179.5 (5) | C18—N3—C14—N2 | 177.8 (5) |
N3—C18—C19—N4 | 177.0 (5) | C19—N4—C15—C16 | 0.8 (9) |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) −x+1, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O4v | 0.88 | 2.21 | 3.042 (6) | 157 |
N3—H3···O4v | 0.88 | 2.36 | 3.174 (6) | 154 |
C2—H2A···O3 | 0.99 | 2.48 | 2.815 (7) | 100 |
C3—H3A···O2 | 0.99 | 2.38 | 2.744 (7) | 101 |
C6—H6A···O7 | 0.99 | 2.47 | 2.825 (7) | 100 |
C7—H7B···O6 | 0.99 | 2.47 | 2.824 (8) | 101 |
C9—H9···O5 | 0.95 | 2.74 | 3.196 (8) | 110 |
C13—H13···O9 | 0.95 | 2.17 | 2.800 (8) | 123 |
C19—H19···O2iv | 0.95 | 2.35 | 2.965 (8) | 122 |
C19—H19···O4vi | 0.95 | 2.84 | 3.126 (7) | 98 |
C19—H19···O9 | 0.95 | 2.15 | 2.786 (8) | 124 |
Symmetry codes: (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+3/2, z+1/2; (vi) −x+1, y−3/2, −z+1/2. |