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In the title complex, [Cu
2(C
8H
4O
4)
2(C
6H
6N
2O)
4]·3H
2O, the Cu
II atom exhibits distorted trigonal–bipyramidal geometry and is coordinated by two N atoms of two isonicotinamide (inta) ligands and three O atoms of three isophthalate (ipt) ligands. C—H
O and N—H
O hydrogen bonds, as well as π–π stacking interactions, are observed between.
Supporting information
CCDC reference: 258821
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.096
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT726_ALERT_1_A H...A Calc 7.83000, Rep 2.55000 Dev... 5.28 Ang.
H22 -O2 1.555 1.555
PLAT726_ALERT_1_A H...A Calc 11.90000, Rep 2.49000 Dev... 9.41 Ang.
H40 -O10 1.555 2.646
PLAT726_ALERT_1_A H...A Calc 19.63000, Rep 2.27000 Dev... 17.36 Ang.
H5A -O2 1.555 1.475
PLAT726_ALERT_1_A H...A Calc 31.84000, Rep 1.93000 Dev... 29.91 Ang.
H8B -O10 1.555 2.556
PLAT726_ALERT_1_A H...A Calc 9.38000, Rep 1.90000 Dev... 7.48 Ang.
H4# -O1# 1.555 1.555
PLAT726_ALERT_1_A H...A Calc 13.88000, Rep 2.05000 Dev... 11.83 Ang.
H1B -O3# 1.555 1.565
PLAT726_ALERT_1_A H...A Calc 24.87000, Rep 2.21000 Dev... 22.66 Ang.
H4B -O2# 1.555 2.767
PLAT727_ALERT_1_A D...A Calc 8.447(4), Rep 3.13000 Dev... 5.32 Ang.
C22 -O2 1.555 1.555
PLAT727_ALERT_1_A D...A Calc 11.987(4), Rep 3.37200 Dev... 8.62 Ang.
C40 -O10 1.555 2.646
PLAT727_ALERT_1_A D...A Calc 20.211(4), Rep 3.09000 Dev... 17.12 Ang.
N5 -O2 1.555 1.475
PLAT727_ALERT_1_A D...A Calc 32.523(5), Rep 2.80100 Dev... 29.72 Ang.
N8 -O10 1.555 2.556
PLAT727_ALERT_1_A D...A Calc 9.016(4), Rep 2.71300 Dev... 6.30 Ang.
O2# -O1# 1.555 1.555
PLAT727_ALERT_1_A D...A Calc 14.114(4), Rep 2.85000 Dev... 11.26 Ang.
N1 -O3# 1.555 1.565
PLAT727_ALERT_1_A D...A Calc 24.756(4), Rep 3.04300 Dev... 21.71 Ang.
N4 -O2# 1.555 2.767
PLAT728_ALERT_1_A D-H..A Calc 129.00, Rep 121.00 Dev... 8.00 Deg.
C22 -H22 -O2 1.555 1.555 1.555
PLAT728_ALERT_1_A D-H..A Calc 93.00, Rep 161.00 Dev... 68.00 Deg.
C40 -H40 -O10 1.555 1.555 2.646
PLAT728_ALERT_1_A D-H..A Calc 131.00, Rep 159.00 Dev... 28.00 Deg.
N5 -H5A -O2 1.555 1.555 1.475
PLAT728_ALERT_1_A D-H..A Calc 142.00, Rep 157.00 Dev... 15.00 Deg.
N8 -H8B -O10 1.555 1.555 2.556
PLAT728_ALERT_1_A D-H..A Calc 62.00, Rep 160.00 Dev... 98.00 Deg.
O2# -H4# -O1# 1.555 1.555 1.555
PLAT728_ALERT_1_A D-H..A Calc 104.00, Rep 155.00 Dev... 51.00 Deg.
N1 -H1B -O3# 1.555 1.555 1.565
PLAT728_ALERT_1_A D-H..A Calc 81.00, Rep 163.00 Dev... 82.00 Deg.
N4 -H4B -O2# 1.555 1.555 2.767
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent O Ueq(max)/Ueq(min) ... 4.01 Ratio
PLAT417_ALERT_2_B Short Inter D-H..H-D H1B .. HW3 .. 1.73 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D HW1 .. H4B .. 2.03 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor OW2 - HW1 ... ?
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.04
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.65 Ratio
PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.92 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.25 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C39
PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ?
PLAT420_ALERT_2_C D-H Without Acceptor N8 - H8A ... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 9
PLAT727_ALERT_1_C D...A Calc 2.853(3), Rep 2.83900 Dev... 0.01 Ang.
O1# -O7 1.555 1.555
PLAT747_ALERT_1_C D...A Calc 8.447(4), Rep 3.13000 ...... Missing su
C22 -O2 1.555 1.555
PLAT747_ALERT_1_C D...A Calc 11.987(4), Rep 3.37200 ...... Missing su
C40 -O10 1.555 2.646
PLAT747_ALERT_1_C D...A Calc 20.211(4), Rep 3.09000 ...... Missing su
N5 -O2 1.555 1.475
PLAT747_ALERT_1_C D...A Calc 32.523(5), Rep 2.80100 ...... Missing su
N8 -O10 1.555 2.556
PLAT747_ALERT_1_C D...A Calc 9.016(4), Rep 2.71300 ...... Missing su
O2# -O1# 1.555 1.555
PLAT747_ALERT_1_C D...A Calc 2.853(3), Rep 2.83900 ...... Missing su
O1# -O7 1.555 1.555
PLAT747_ALERT_1_C D...A Calc 14.114(4), Rep 2.85000 ...... Missing su
N1 -O3# 1.555 1.565
PLAT747_ALERT_1_C D...A Calc 24.756(4), Rep 3.04300 ...... Missing su
N4 -O2# 1.555 2.767
PLAT804_ALERT_4_C ARU-Pack Problem in PLATON Analysis ............ !
PLAT804_ALERT_4_C ARU-Pack Problem in PLATON Analysis ............ !
21 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
23 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
33 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 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
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
di-µ-isophthalato-bis[bis(isonicotinamide)copper(II)] trihydrate
top
Crystal data top
[Cu2(C8H4O4)2(C6H6N2O)4]·3H2O | Z = 2 |
Mr = 997.86 | F(000) = 1024 |
Triclinic, P1 | Dx = 1.599 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0909 (7) Å | Cell parameters from 10290 reflections |
b = 12.7898 (9) Å | θ = 1.7–28.3° |
c = 17.5601 (12) Å | µ = 1.11 mm−1 |
α = 95.6425 (12)° | T = 293 K |
β = 99.8511 (13)° | Block, blue |
γ = 109.6652 (11)° | 0.43 × 0.19 × 0.13 mm |
V = 2072.8 (2) Å3 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 9109 independent reflections |
Radiation source: fine-focus sealed tube | 6542 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 28.3°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→13 |
Tmin = 0.801, Tmax = 0.838 | k = −16→16 |
12901 measured reflections | l = −23→18 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.021P)2 + 0.9P] where P = (Fo2 + 2Fc2)/3 |
9109 reflections | (Δ/σ)max = 0.001 |
592 parameters | Δρmax = 0.77 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.85425 (3) | −0.53720 (3) | 0.819636 (19) | 0.02509 (10) | |
Cu2 | 1.14283 (3) | −0.43811 (3) | 0.671911 (19) | 0.02604 (10) | |
N7 | 1.0699 (2) | −0.60625 (18) | 0.63251 (13) | 0.0260 (5) | |
N6 | 1.2144 (2) | −0.27464 (18) | 0.72413 (13) | 0.0285 (5) | |
N2 | 0.9620 (2) | −0.37792 (17) | 0.87744 (13) | 0.0273 (5) | |
N3 | 0.7464 (2) | −0.69335 (18) | 0.75504 (13) | 0.0282 (5) | |
C29 | 0.9447 (3) | −0.6649 (2) | 0.58117 (16) | 0.0325 (7) | |
H29 | 0.8924 | −0.6256 | 0.5561 | 0.039* | |
C1 | 1.3829 (3) | −0.5667 (2) | 0.86615 (15) | 0.0230 (6) | |
H1 | 1.4013 | −0.5325 | 0.8228 | 0.028* | |
C8 | 1.1411 (3) | −0.5459 (2) | 0.84170 (16) | 0.0245 (6) | |
C2 | 1.4874 (3) | −0.5995 (2) | 0.90949 (15) | 0.0224 (6) | |
C9 | 0.8522 (3) | −0.4364 (2) | 0.64600 (15) | 0.0232 (6) | |
C7 | 1.2513 (3) | −0.5850 (2) | 0.88771 (15) | 0.0231 (6) | |
C6 | 1.2248 (3) | −0.6367 (2) | 0.95208 (16) | 0.0281 (6) | |
H6 | 1.1360 | −0.6512 | 0.9656 | 0.034* | |
C4 | 1.4605 (3) | −0.6480 (2) | 0.97474 (15) | 0.0266 (6) | |
H4 | 1.5309 | −0.6683 | 1.0044 | 0.032* | |
C10 | 0.7396 (3) | −0.4017 (2) | 0.59801 (15) | 0.0220 (5) | |
C5 | 1.3294 (3) | −0.6670 (2) | 0.99667 (16) | 0.0289 (6) | |
H5 | 1.3119 | −0.6998 | 1.0407 | 0.035* | |
C23 | 0.7876 (3) | −0.7804 (2) | 0.76497 (18) | 0.0367 (7) | |
H23 | 0.8722 | −0.7684 | 0.8013 | 0.044* | |
C40 | 0.8908 (3) | −0.7810 (2) | 0.56424 (18) | 0.0374 (7) | |
H40 | 0.8037 | −0.8189 | 0.5286 | 0.045* | |
C38 | 0.9674 (3) | −0.8408 (2) | 0.60073 (18) | 0.0371 (7) | |
C36 | 1.1459 (3) | −0.6651 (2) | 0.66525 (16) | 0.0312 (6) | |
H36 | 1.2351 | −0.6254 | 0.6986 | 0.037* | |
C30 | 1.1747 (3) | −0.1983 (2) | 0.68907 (18) | 0.0381 (7) | |
H30 | 1.1087 | −0.2228 | 0.6412 | 0.046* | |
C37 | 1.0987 (3) | −0.7804 (2) | 0.65204 (17) | 0.0341 (7) | |
H37 | 1.1538 | −0.8176 | 0.6771 | 0.041* | |
C34 | 1.3682 (3) | −0.1242 (2) | 0.82790 (18) | 0.0381 (7) | |
H34 | 1.4351 | −0.1013 | 0.8754 | 0.046* | |
C25 | 0.5850 (3) | −0.9078 (2) | 0.66917 (17) | 0.0346 (7) | |
C32 | 1.3264 (3) | −0.0460 (2) | 0.79050 (18) | 0.0346 (7) | |
C21 | 1.1350 (3) | −0.2445 (2) | 0.98401 (17) | 0.0343 (7) | |
H21 | 1.2022 | −0.2311 | 1.0307 | 0.041* | |
C17 | 0.9343 (3) | −0.2917 (2) | 0.84979 (18) | 0.0375 (7) | |
H17 | 0.8641 | −0.3074 | 0.8041 | 0.045* | |
C27 | 0.5428 (3) | −0.8171 (2) | 0.65836 (18) | 0.0436 (8) | |
H27 | 0.4595 | −0.8268 | 0.6217 | 0.052* | |
C33 | 1.3849 (4) | 0.0790 (3) | 0.82118 (19) | 0.0415 (8) | |
C35 | 1.3091 (3) | −0.2363 (2) | 0.79359 (17) | 0.0355 (7) | |
H35 | 1.3363 | −0.2881 | 0.8199 | 0.043* | |
C28 | 0.6237 (3) | −0.7133 (2) | 0.70169 (18) | 0.0421 (8) | |
H28 | 0.5927 | −0.6536 | 0.6940 | 0.050* | |
C19 | 1.1080 (3) | −0.1554 (2) | 0.95457 (18) | 0.0338 (7) | |
C22 | 1.0626 (3) | −0.3525 (2) | 0.94441 (16) | 0.0317 (6) | |
H22 | 1.0839 | −0.4108 | 0.9648 | 0.038* | |
C31 | 1.2267 (3) | −0.0850 (2) | 0.72019 (18) | 0.0405 (8) | |
H31 | 1.1947 | −0.0354 | 0.6939 | 0.049* | |
C24 | 0.7104 (3) | −0.8883 (2) | 0.72367 (19) | 0.0410 (8) | |
H24 | 0.7428 | −0.9469 | 0.7326 | 0.049* | |
C18 | 1.0044 (3) | −0.1814 (2) | 0.88560 (19) | 0.0411 (8) | |
H18 | 0.9824 | −0.1243 | 0.8637 | 0.049* | |
C26 | 0.4912 (4) | −1.0216 (3) | 0.62202 (19) | 0.0457 (8) | |
C20 | 1.1919 (4) | −0.0375 (3) | 0.9973 (2) | 0.0489 (9) | |
C39 | 0.9148 (4) | −0.9677 (3) | 0.5934 (2) | 0.0586 (11) | |
C13 | 0.3684 (3) | −0.3917 (2) | 0.60512 (16) | 0.0252 (6) | |
C3 | 1.6294 (3) | −0.5820 (2) | 0.88655 (16) | 0.0244 (6) | |
C12 | 0.5069 (3) | −0.3805 (2) | 0.57966 (15) | 0.0235 (6) | |
C11 | 0.6114 (3) | −0.4143 (2) | 0.62214 (15) | 0.0237 (6) | |
H11 | 0.5952 | −0.4455 | 0.6669 | 0.028* | |
C14 | 0.5309 (3) | −0.3373 (2) | 0.51227 (15) | 0.0284 (6) | |
H14 | 0.4610 | −0.3160 | 0.4832 | 0.034* | |
C16 | 0.7624 (3) | −0.3567 (2) | 0.53070 (16) | 0.0292 (6) | |
H16 | 0.8481 | −0.3476 | 0.5145 | 0.035* | |
C15 | 0.6576 (3) | −0.3252 (2) | 0.48724 (17) | 0.0322 (6) | |
H15 | 0.6724 | −0.2961 | 0.4416 | 0.039* | |
O4 | 1.1773 (2) | −0.48180 (16) | 0.79492 (11) | 0.0317 (4) | |
O6 | 0.8293 (2) | −0.47316 (17) | 0.70611 (12) | 0.0391 (5) | |
O3 | 1.01672 (19) | −0.58179 (15) | 0.85759 (12) | 0.0321 (5) | |
O9 | 1.2787 (3) | −0.0207 (2) | 1.06012 (16) | 0.0733 (9) | |
N1 | 1.1704 (3) | 0.0458 (2) | 0.96495 (19) | 0.0662 (10) | |
H1A | 1.2175 | 0.1144 | 0.9876 | 0.079* | |
H1B | 1.1093 | 0.0316 | 0.9212 | 0.079* | |
N8 | 0.8025 (4) | −1.0281 (2) | 0.5373 (2) | 0.0761 (11) | |
H8A | 0.7681 | −1.1002 | 0.5333 | 0.091* | |
H8B | 0.7634 | −0.9954 | 0.5046 | 0.091* | |
N5 | 1.5086 (3) | 0.1199 (2) | 0.87421 (17) | 0.0532 (8) | |
H5A | 1.5464 | 0.1909 | 0.8923 | 0.064* | |
H5B | 1.5507 | 0.0754 | 0.8904 | 0.064* | |
O10 | 0.3938 (3) | −1.0299 (2) | 0.56774 (15) | 0.0796 (10) | |
O12 | 0.9725 (4) | −1.0112 (2) | 0.6405 (2) | 0.1106 (14) | |
O11 | 1.3204 (3) | 0.13879 (18) | 0.79610 (16) | 0.0632 (7) | |
O5 | 0.96438 (19) | −0.42416 (16) | 0.61892 (11) | 0.0324 (5) | |
N4 | 0.5176 (3) | −1.1105 (2) | 0.64262 (18) | 0.0560 (8) | |
H4A | 0.4650 | −1.1767 | 0.6173 | 0.067* | |
H4B | 0.5873 | −1.1020 | 0.6813 | 0.067* | |
O2 | 1.7077 (2) | −0.62947 (17) | 0.91849 (12) | 0.0375 (5) | |
O8 | 0.2802 (2) | −0.35998 (18) | 0.56429 (12) | 0.0425 (5) | |
O1 | 1.66369 (19) | −0.52172 (14) | 0.83445 (11) | 0.0276 (4) | |
O7 | 0.34834 (19) | −0.42901 (15) | 0.66843 (11) | 0.0276 (4) | |
OW3 | 0.5791 (2) | −0.33497 (17) | 0.80320 (12) | 0.0454 (6) | |
HW6 | 0.6050 | −0.3889 | 0.8147 | 0.054* | |
HW5 | 0.5104 | −0.3610 | 0.7627 | 0.054* | |
OW2 | 1.2853 (3) | 0.1154 (2) | 1.20693 (19) | 0.0910 (10) | |
HW1 | 1.2556 | 0.1337 | 1.2471 | 0.109* | |
HW2 | 1.3347 | 0.1773 | 1.1948 | 0.109* | |
OW1 | 1.0293 (3) | 0.0719 (2) | 0.81552 (18) | 0.0929 (10) | |
HW3 | 0.9850 | 0.0579 | 0.8526 | 0.112* | |
HW4 | 0.9978 | 0.0132 | 0.7808 | 0.112* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.01625 (17) | 0.02675 (18) | 0.03361 (19) | 0.01125 (14) | 0.00268 (14) | 0.00343 (14) |
Cu2 | 0.01551 (17) | 0.03001 (19) | 0.0333 (2) | 0.01155 (14) | 0.00198 (14) | 0.00237 (14) |
N7 | 0.0214 (12) | 0.0308 (12) | 0.0269 (12) | 0.0115 (10) | 0.0044 (10) | 0.0040 (10) |
N6 | 0.0223 (12) | 0.0306 (12) | 0.0342 (13) | 0.0127 (10) | 0.0044 (10) | 0.0042 (10) |
N2 | 0.0201 (12) | 0.0264 (12) | 0.0368 (13) | 0.0098 (10) | 0.0061 (10) | 0.0065 (10) |
N3 | 0.0261 (13) | 0.0282 (12) | 0.0312 (13) | 0.0135 (10) | 0.0021 (10) | 0.0035 (10) |
C29 | 0.0275 (16) | 0.0362 (16) | 0.0334 (16) | 0.0149 (13) | −0.0006 (13) | 0.0051 (13) |
C1 | 0.0192 (13) | 0.0248 (13) | 0.0260 (14) | 0.0097 (11) | 0.0032 (11) | 0.0053 (11) |
C8 | 0.0174 (13) | 0.0246 (13) | 0.0291 (15) | 0.0096 (11) | 0.0003 (11) | −0.0049 (11) |
C2 | 0.0154 (13) | 0.0222 (13) | 0.0283 (14) | 0.0077 (10) | 0.0022 (11) | −0.0002 (11) |
C9 | 0.0163 (13) | 0.0226 (13) | 0.0297 (15) | 0.0082 (11) | 0.0022 (11) | 0.0009 (11) |
C7 | 0.0175 (13) | 0.0235 (13) | 0.0279 (14) | 0.0089 (11) | 0.0027 (11) | 0.0015 (11) |
C6 | 0.0192 (14) | 0.0315 (15) | 0.0358 (16) | 0.0107 (12) | 0.0089 (12) | 0.0044 (12) |
C4 | 0.0237 (14) | 0.0260 (14) | 0.0302 (15) | 0.0124 (11) | −0.0011 (12) | 0.0040 (11) |
C10 | 0.0185 (13) | 0.0235 (13) | 0.0239 (13) | 0.0089 (11) | 0.0022 (11) | 0.0020 (10) |
C5 | 0.0301 (16) | 0.0299 (15) | 0.0280 (15) | 0.0112 (12) | 0.0073 (12) | 0.0081 (12) |
C23 | 0.0294 (16) | 0.0334 (16) | 0.0442 (18) | 0.0137 (13) | −0.0035 (14) | 0.0039 (13) |
C40 | 0.0275 (16) | 0.0342 (16) | 0.0418 (18) | 0.0071 (13) | −0.0044 (14) | 0.0015 (14) |
C38 | 0.0346 (17) | 0.0336 (16) | 0.0410 (18) | 0.0125 (14) | 0.0025 (14) | 0.0049 (13) |
C36 | 0.0212 (14) | 0.0380 (16) | 0.0330 (16) | 0.0121 (13) | 0.0006 (12) | 0.0028 (13) |
C30 | 0.0331 (17) | 0.0361 (16) | 0.0402 (18) | 0.0122 (14) | −0.0028 (14) | 0.0041 (14) |
C37 | 0.0322 (17) | 0.0323 (15) | 0.0398 (17) | 0.0171 (13) | 0.0016 (13) | 0.0074 (13) |
C34 | 0.0322 (17) | 0.0362 (16) | 0.0407 (18) | 0.0124 (14) | −0.0038 (14) | 0.0023 (14) |
C25 | 0.0349 (17) | 0.0308 (15) | 0.0333 (16) | 0.0092 (13) | 0.0024 (13) | 0.0021 (13) |
C32 | 0.0299 (16) | 0.0320 (16) | 0.0433 (18) | 0.0135 (13) | 0.0081 (14) | 0.0040 (13) |
C21 | 0.0282 (16) | 0.0350 (16) | 0.0349 (16) | 0.0109 (13) | −0.0029 (13) | 0.0031 (13) |
C17 | 0.0310 (17) | 0.0371 (17) | 0.0423 (18) | 0.0164 (14) | −0.0040 (14) | 0.0045 (14) |
C27 | 0.0376 (19) | 0.0367 (17) | 0.0458 (19) | 0.0128 (15) | −0.0149 (15) | 0.0017 (14) |
C33 | 0.0412 (19) | 0.0344 (17) | 0.050 (2) | 0.0177 (15) | 0.0080 (16) | 0.0025 (15) |
C35 | 0.0334 (17) | 0.0331 (16) | 0.0420 (17) | 0.0179 (14) | 0.0009 (14) | 0.0072 (13) |
C28 | 0.0357 (18) | 0.0352 (17) | 0.053 (2) | 0.0190 (15) | −0.0072 (15) | 0.0054 (15) |
C19 | 0.0285 (16) | 0.0277 (15) | 0.0426 (17) | 0.0100 (13) | 0.0026 (13) | 0.0045 (13) |
C22 | 0.0287 (16) | 0.0307 (15) | 0.0376 (16) | 0.0146 (13) | 0.0031 (13) | 0.0081 (13) |
C31 | 0.0400 (19) | 0.0353 (17) | 0.0492 (19) | 0.0215 (15) | 0.0010 (15) | 0.0083 (14) |
C24 | 0.0378 (18) | 0.0318 (16) | 0.053 (2) | 0.0176 (14) | −0.0008 (15) | 0.0041 (14) |
C18 | 0.0379 (18) | 0.0308 (16) | 0.054 (2) | 0.0172 (14) | −0.0040 (15) | 0.0090 (14) |
C26 | 0.051 (2) | 0.0325 (17) | 0.0431 (19) | 0.0070 (16) | 0.0036 (16) | −0.0013 (14) |
C20 | 0.040 (2) | 0.0355 (18) | 0.062 (2) | 0.0133 (16) | −0.0049 (17) | 0.0000 (16) |
C39 | 0.050 (2) | 0.0343 (18) | 0.076 (3) | 0.0113 (17) | −0.015 (2) | 0.0025 (18) |
C13 | 0.0153 (13) | 0.0271 (14) | 0.0325 (15) | 0.0089 (11) | 0.0036 (11) | 0.0003 (12) |
C3 | 0.0161 (13) | 0.0245 (13) | 0.0322 (15) | 0.0100 (11) | 0.0015 (11) | −0.0005 (11) |
C12 | 0.0174 (13) | 0.0255 (13) | 0.0273 (14) | 0.0092 (11) | 0.0028 (11) | 0.0018 (11) |
C11 | 0.0202 (14) | 0.0262 (13) | 0.0263 (14) | 0.0108 (11) | 0.0035 (11) | 0.0052 (11) |
C14 | 0.0242 (15) | 0.0355 (15) | 0.0301 (15) | 0.0175 (12) | 0.0025 (12) | 0.0083 (12) |
C16 | 0.0196 (14) | 0.0386 (16) | 0.0319 (15) | 0.0122 (12) | 0.0095 (12) | 0.0045 (12) |
C15 | 0.0312 (16) | 0.0427 (17) | 0.0303 (15) | 0.0183 (14) | 0.0111 (13) | 0.0154 (13) |
O4 | 0.0271 (11) | 0.0418 (12) | 0.0320 (11) | 0.0188 (9) | 0.0054 (9) | 0.0114 (9) |
O6 | 0.0300 (12) | 0.0578 (14) | 0.0393 (12) | 0.0239 (10) | 0.0093 (10) | 0.0216 (11) |
O3 | 0.0160 (10) | 0.0330 (11) | 0.0509 (13) | 0.0126 (8) | 0.0065 (9) | 0.0109 (9) |
O9 | 0.077 (2) | 0.0449 (14) | 0.0741 (18) | 0.0207 (14) | −0.0327 (15) | −0.0111 (13) |
N1 | 0.071 (2) | 0.0241 (14) | 0.080 (2) | 0.0074 (15) | −0.0203 (18) | −0.0002 (14) |
N8 | 0.078 (3) | 0.0312 (16) | 0.089 (3) | 0.0082 (16) | −0.031 (2) | 0.0011 (16) |
N5 | 0.0460 (18) | 0.0305 (14) | 0.071 (2) | 0.0128 (13) | −0.0077 (15) | −0.0056 (14) |
O10 | 0.088 (2) | 0.0479 (16) | 0.0650 (18) | 0.0074 (15) | −0.0398 (16) | −0.0012 (13) |
O12 | 0.098 (3) | 0.0407 (16) | 0.154 (3) | 0.0195 (17) | −0.064 (2) | 0.0150 (17) |
O11 | 0.0620 (17) | 0.0380 (13) | 0.0836 (19) | 0.0255 (13) | −0.0095 (14) | −0.0001 (12) |
O5 | 0.0186 (10) | 0.0457 (12) | 0.0382 (11) | 0.0182 (9) | 0.0060 (9) | 0.0080 (9) |
N4 | 0.062 (2) | 0.0277 (14) | 0.066 (2) | 0.0103 (14) | −0.0008 (16) | −0.0052 (13) |
O2 | 0.0257 (11) | 0.0510 (13) | 0.0468 (12) | 0.0261 (10) | 0.0065 (9) | 0.0167 (10) |
O8 | 0.0282 (12) | 0.0702 (15) | 0.0424 (12) | 0.0328 (11) | 0.0073 (10) | 0.0168 (11) |
O1 | 0.0189 (10) | 0.0297 (10) | 0.0394 (11) | 0.0136 (8) | 0.0089 (8) | 0.0074 (9) |
O7 | 0.0170 (9) | 0.0353 (10) | 0.0351 (11) | 0.0136 (8) | 0.0073 (8) | 0.0084 (9) |
OW3 | 0.0450 (14) | 0.0422 (12) | 0.0465 (13) | 0.0217 (11) | −0.0069 (11) | 0.0044 (10) |
OW2 | 0.079 (2) | 0.0583 (18) | 0.124 (3) | 0.0173 (16) | −0.0070 (19) | 0.0370 (17) |
OW1 | 0.088 (2) | 0.103 (2) | 0.094 (2) | 0.050 (2) | 0.0008 (19) | 0.0253 (19) |
Geometric parameters (Å, º) top
Cu1—O3 | 1.9461 (17) | C25—C26 | 1.507 (4) |
Cu1—N2 | 2.022 (2) | C32—C31 | 1.379 (4) |
Cu1—N3 | 2.032 (2) | C32—C33 | 1.510 (4) |
Cu1—O1i | 2.0546 (17) | C21—C22 | 1.373 (4) |
Cu1—O6 | 2.235 (2) | C21—C19 | 1.384 (4) |
Cu2—O5 | 1.9535 (18) | C21—H21 | 0.9300 |
Cu2—N7 | 2.028 (2) | C17—C18 | 1.375 (4) |
Cu2—N6 | 2.028 (2) | C17—H17 | 0.9300 |
Cu2—O7ii | 2.0494 (17) | C27—C28 | 1.367 (4) |
Cu2—O4 | 2.2825 (19) | C27—H27 | 0.9300 |
N7—C36 | 1.344 (3) | C33—O11 | 1.227 (4) |
N7—C29 | 1.346 (3) | C33—N5 | 1.329 (4) |
N6—C30 | 1.338 (3) | C35—H35 | 0.9300 |
N6—C35 | 1.345 (4) | C28—H28 | 0.9300 |
N2—C17 | 1.340 (3) | C19—C18 | 1.387 (4) |
N2—C22 | 1.347 (3) | C19—C20 | 1.501 (4) |
N3—C23 | 1.330 (3) | C22—H22 | 0.9300 |
N3—C28 | 1.349 (3) | C31—H31 | 0.9300 |
C29—C40 | 1.380 (4) | C24—H24 | 0.9300 |
C29—H29 | 0.9300 | C18—H18 | 0.9300 |
C1—C7 | 1.393 (3) | C26—O10 | 1.215 (4) |
C1—C2 | 1.397 (3) | C26—N4 | 1.321 (4) |
C1—H1 | 0.9300 | C20—O9 | 1.235 (4) |
C8—O4 | 1.231 (3) | C20—N1 | 1.319 (4) |
C8—O3 | 1.273 (3) | C39—O12 | 1.215 (4) |
C8—C7 | 1.512 (3) | C39—N8 | 1.316 (4) |
C2—C4 | 1.380 (4) | C13—O8 | 1.245 (3) |
C2—C3 | 1.504 (4) | C13—O7 | 1.273 (3) |
C9—O6 | 1.223 (3) | C13—C12 | 1.505 (4) |
C9—O5 | 1.269 (3) | C3—O2 | 1.243 (3) |
C9—C10 | 1.512 (3) | C3—O1 | 1.272 (3) |
C7—C6 | 1.384 (4) | C12—C14 | 1.378 (4) |
C6—C5 | 1.390 (4) | C12—C11 | 1.399 (3) |
C6—H6 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.391 (4) | C14—C15 | 1.387 (4) |
C4—H4 | 0.9300 | C14—H14 | 0.9300 |
C10—C16 | 1.385 (4) | C16—C15 | 1.391 (4) |
C10—C11 | 1.392 (4) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C23—C24 | 1.386 (4) | N1—H1A | 0.8600 |
C23—H23 | 0.9300 | N1—H1B | 0.8600 |
C40—C38 | 1.384 (4) | N8—H8A | 0.8600 |
C40—H40 | 0.9300 | N8—H8B | 0.8600 |
C38—C37 | 1.389 (4) | N5—H5A | 0.8600 |
C38—C39 | 1.513 (4) | N5—H5B | 0.8600 |
C36—C37 | 1.370 (4) | N4—H4A | 0.8600 |
C36—H36 | 0.9300 | N4—H4B | 0.8600 |
C30—C31 | 1.381 (4) | O1—Cu1ii | 2.0546 (17) |
C30—H30 | 0.9300 | O7—Cu2i | 2.0494 (17) |
C37—H37 | 0.9300 | OW3—HW6 | 0.8458 |
C34—C35 | 1.381 (4) | OW3—HW5 | 0.8522 |
C34—C32 | 1.388 (4) | OW2—HW1 | 0.8533 |
C34—H34 | 0.9300 | OW2—HW2 | 0.8508 |
C25—C24 | 1.380 (4) | OW1—HW3 | 0.8515 |
C25—C27 | 1.382 (4) | OW1—HW4 | 0.8475 |
| | | |
O3—Cu1—N2 | 91.51 (8) | C31—C32—C33 | 118.0 (3) |
O3—Cu1—N3 | 89.99 (8) | C34—C32—C33 | 124.2 (3) |
N2—Cu1—N3 | 176.35 (9) | C22—C21—C19 | 120.1 (3) |
O3—Cu1—O1i | 148.86 (8) | C22—C21—H21 | 120.0 |
N2—Cu1—O1i | 89.50 (8) | C19—C21—H21 | 120.0 |
N3—Cu1—O1i | 90.94 (8) | N2—C17—C18 | 123.3 (3) |
O3—Cu1—O6 | 121.70 (8) | N2—C17—H17 | 118.3 |
N2—Cu1—O6 | 90.30 (8) | C18—C17—H17 | 118.3 |
N3—Cu1—O6 | 86.09 (8) | C28—C27—C25 | 119.8 (3) |
O1i—Cu1—O6 | 89.41 (7) | C28—C27—H27 | 120.1 |
O5—Cu2—N7 | 92.72 (8) | C25—C27—H27 | 120.1 |
O5—Cu2—N6 | 89.78 (8) | O11—C33—N5 | 122.6 (3) |
N7—Cu2—N6 | 173.22 (9) | O11—C33—C32 | 120.2 (3) |
O5—Cu2—O7ii | 147.80 (8) | N5—C33—C32 | 117.2 (3) |
N7—Cu2—O7ii | 89.62 (8) | N6—C35—C34 | 123.4 (3) |
N6—Cu2—O7ii | 91.62 (8) | N6—C35—H35 | 118.3 |
O5—Cu2—O4 | 123.53 (7) | C34—C35—H35 | 118.3 |
N7—Cu2—O4 | 86.33 (8) | N3—C28—C27 | 123.0 (3) |
N6—Cu2—O4 | 87.03 (8) | N3—C28—H28 | 118.5 |
O7ii—Cu2—O4 | 88.66 (7) | C27—C28—H28 | 118.5 |
C36—N7—C29 | 117.4 (2) | C21—C19—C18 | 117.0 (3) |
C36—N7—Cu2 | 117.47 (18) | C21—C19—C20 | 119.3 (3) |
C29—N7—Cu2 | 124.90 (18) | C18—C19—C20 | 123.7 (3) |
C30—N6—C35 | 116.6 (2) | N2—C22—C21 | 123.0 (2) |
C30—N6—Cu2 | 121.30 (19) | N2—C22—H22 | 118.5 |
C35—N6—Cu2 | 122.00 (18) | C21—C22—H22 | 118.5 |
C17—N2—C22 | 116.8 (2) | C32—C31—C30 | 119.6 (3) |
C17—N2—Cu1 | 120.22 (19) | C32—C31—H31 | 120.2 |
C22—N2—Cu1 | 122.96 (18) | C30—C31—H31 | 120.2 |
C23—N3—C28 | 117.1 (2) | C25—C24—C23 | 119.4 (3) |
C23—N3—Cu1 | 122.90 (19) | C25—C24—H24 | 120.3 |
C28—N3—Cu1 | 119.91 (18) | C23—C24—H24 | 120.3 |
N7—C29—C40 | 122.5 (3) | C17—C18—C19 | 119.8 (3) |
N7—C29—H29 | 118.8 | C17—C18—H18 | 120.1 |
C40—C29—H29 | 118.8 | C19—C18—H18 | 120.1 |
C7—C1—C2 | 120.2 (2) | O10—C26—N4 | 122.0 (3) |
C7—C1—H1 | 119.9 | O10—C26—C25 | 120.2 (3) |
C2—C1—H1 | 119.9 | N4—C26—C25 | 117.8 (3) |
O4—C8—O3 | 125.7 (2) | O9—C20—N1 | 122.1 (3) |
O4—C8—C7 | 119.4 (2) | O9—C20—C19 | 120.3 (3) |
O3—C8—C7 | 114.9 (2) | N1—C20—C19 | 117.6 (3) |
C4—C2—C1 | 119.5 (2) | O12—C39—N8 | 121.6 (3) |
C4—C2—C3 | 119.4 (2) | O12—C39—C38 | 120.0 (3) |
C1—C2—C3 | 121.1 (2) | N8—C39—C38 | 118.3 (3) |
O6—C9—O5 | 125.7 (2) | O8—C13—O7 | 122.8 (2) |
O6—C9—C10 | 118.9 (2) | O8—C13—C12 | 118.1 (3) |
O5—C9—C10 | 115.3 (2) | O7—C13—C12 | 119.1 (2) |
C6—C7—C1 | 119.4 (2) | O2—C3—O1 | 122.4 (3) |
C6—C7—C8 | 121.0 (2) | O2—C3—C2 | 118.2 (3) |
C1—C7—C8 | 119.6 (2) | O1—C3—C2 | 119.3 (2) |
C7—C6—C5 | 120.8 (3) | C14—C12—C11 | 119.0 (2) |
C7—C6—H6 | 119.6 | C14—C12—C13 | 119.3 (2) |
C5—C6—H6 | 119.6 | C11—C12—C13 | 121.6 (2) |
C2—C4—C5 | 120.7 (2) | C10—C11—C12 | 120.6 (2) |
C2—C4—H4 | 119.6 | C10—C11—H11 | 119.7 |
C5—C4—H4 | 119.6 | C12—C11—H11 | 119.7 |
C16—C10—C11 | 119.5 (2) | C12—C14—C15 | 121.0 (2) |
C16—C10—C9 | 121.0 (2) | C12—C14—H14 | 119.5 |
C11—C10—C9 | 119.5 (2) | C15—C14—H14 | 119.5 |
C6—C5—C4 | 119.3 (3) | C10—C16—C15 | 120.2 (3) |
C6—C5—H5 | 120.3 | C10—C16—H16 | 119.9 |
C4—C5—H5 | 120.3 | C15—C16—H16 | 119.9 |
N3—C23—C24 | 123.0 (3) | C14—C15—C16 | 119.7 (3) |
N3—C23—H23 | 118.5 | C14—C15—H15 | 120.2 |
C24—C23—H23 | 118.5 | C16—C15—H15 | 120.2 |
C29—C40—C38 | 119.5 (3) | C8—O4—Cu2 | 150.25 (18) |
C29—C40—H40 | 120.2 | C9—O6—Cu1 | 163.22 (18) |
C38—C40—H40 | 120.2 | C8—O3—Cu1 | 126.89 (18) |
C40—C38—C37 | 118.1 (3) | C20—N1—H1A | 120.0 |
C40—C38—C39 | 125.0 (3) | C20—N1—H1B | 120.0 |
C37—C38—C39 | 116.8 (3) | H1A—N1—H1B | 120.0 |
N7—C36—C37 | 123.4 (3) | C39—N8—H8A | 120.0 |
N7—C36—H36 | 118.3 | C39—N8—H8B | 120.0 |
C37—C36—H36 | 118.3 | H8A—N8—H8B | 120.0 |
N6—C30—C31 | 123.5 (3) | C33—N5—H5A | 120.0 |
N6—C30—H30 | 118.3 | C33—N5—H5B | 120.0 |
C31—C30—H30 | 118.3 | H5A—N5—H5B | 120.0 |
C36—C37—C38 | 119.0 (3) | C9—O5—Cu2 | 126.78 (18) |
C36—C37—H37 | 120.5 | C26—N4—H4A | 120.0 |
C38—C37—H37 | 120.5 | C26—N4—H4B | 120.0 |
C35—C34—C32 | 119.2 (3) | H4A—N4—H4B | 120.0 |
C35—C34—H34 | 120.4 | C3—O1—Cu1ii | 103.14 (15) |
C32—C34—H34 | 120.4 | C13—O7—Cu2i | 103.61 (15) |
C24—C25—C27 | 117.6 (3) | HW6—OW3—HW5 | 107.1 |
C24—C25—C26 | 124.0 (3) | HW1—OW2—HW2 | 105.6 |
C27—C25—C26 | 118.4 (3) | HW3—OW1—HW4 | 108.3 |
C31—C32—C34 | 117.7 (3) | | |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O2 | 0.93 | 2.55 | 3.130 (?) | 121 |
C40—H40···O10iii | 0.93 | 2.49 | 3.372 (?) | 161 |
N5—H5A···O2iv | 0.86 | 2.27 | 3.090 (?) | 159 |
N8—H8B···O10v | 0.86 | 1.93 | 2.801 (?) | 157 |
OW2—HW2···OW3 | 0.85 | 1.90 | 2.713 (?) | 160 |
OW3—HW5···O7 | 0.85 | 2.00 | 2.839 (?) | 177 |
N1—H1B···OW1vi | 0.86 | 2.05 | 2.850 (?) | 155 |
N4—H4B···OW2vii | 0.86 | 2.21 | 3.043 (?) | 163 |
Symmetry codes: (iii) −x+1, −y−1, −z+1; (iv) x−1, y+2, z; (v) −x, −y, −z+1; (vi) x, y+1, z; (vii) −x+2, −y+1, −z+2. |
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