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In the title complex, [Cu(C6H10O7)(C10H9N3)(H2O)]·3H2O, the Cu atom has a distorted square-pyramidal geometry coordinated by two O atoms of a D-gluconate ligand, two N atoms of a bidentate di-2-pyridylamine ligand and a water O atom. The deprotonated α-hydroxyl and carbonate O atoms of the D-gluconate ligand form a five-membered chelate ring with the Cu atom. The crystal structure is stabilized both by all of the available hydrogen bonds and by π–π stacking inter­actions between di-2-pyridylamine ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029102/tk2064sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029102/tk2064Isup2.hkl
Contains datablock I

CCDC reference: 621510

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.045
  • wR factor = 0.086
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H23 .. H25 .. 2.01 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H25 .. H27 .. 2.08 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.02 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT417_ALERT_2_C Short Inter D-H..H-D H17 .. H24 .. 2.12 Ang. PLAT417_ALERT_2_C Short Inter D-H..H-D H24 .. H27 .. 2.11 Ang.
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 27.50 From the CIF: _reflns_number_total 4365 Count of symmetry unique reflns 2579 Completeness (_total/calc) 169.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1786 Fraction of Friedel pairs measured 0.693 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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, 2005) and CRYSTALS (Betteridge et al., 2003); program(s) used to solve structure: SHELXLS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976), ORTEP-3 for Windows (Farrugia, 1997) and ORTEX (McArdle, 1995); software used to prepare material for publication: CrystalStructure.

Aqua(di-2-pyridylamine-κ2N2,N2')(D-gluconato-κ2O,O')copper(II) trihydrate top
Crystal data top
[Cu(C6H10O7)(C10H9N3)(H2O)]·3H2OF(000) = 522.00
Mr = 500.96Dx = 1.629 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ybCell parameters from 7711 reflections
a = 13.02 (1) Åθ = 3.1–27.5°
b = 5.447 (5) ŵ = 1.14 mm1
c = 14.52 (1) ÅT = 123 K
β = 97.34 (4)°Needle, light-blue
V = 1021.3 (14) Å30.40 × 0.05 × 0.01 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2251 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.074
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1616
Tmin = 0.576, Tmax = 0.989k = 76
10058 measured reflectionsl = 1818
4365 independent reflections
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0255P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.045(Δ/σ)max < 0.001
wR(F2) = 0.086Δρmax = 0.58 e Å3
S = 0.85Δρmin = 0.55 e Å3
4365 reflectionsAbsolute structure: Flack (1983), 1792 Friedel pairs
294 parametersAbsolute structure parameter: 0.05 (2)
H-atom parameters constrained
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.31756 (4)0.3039 (1)0.17393 (4)0.0197 (1)
O10.2609 (2)0.2807 (7)0.0422 (2)0.0187 (7)
O20.1282 (3)0.3962 (5)0.0599 (2)0.0240 (8)
O30.2056 (3)0.5331 (5)0.1812 (2)0.0181 (8)
O40.0451 (3)0.1520 (6)0.1178 (3)0.024 (1)
O50.0572 (3)0.4507 (6)0.2819 (2)0.0258 (8)
O60.1970 (3)0.4455 (6)0.1403 (3)0.039 (1)
O70.2335 (3)0.2558 (7)0.3209 (3)0.039 (1)
O80.2150 (3)0.0107 (6)0.2371 (3)0.0218 (8)
O90.2130 (3)0.0962 (7)0.4333 (3)0.044 (1)
O100.0481 (3)0.781 (1)0.4213 (3)0.061 (1)
O110.1467 (3)0.4501 (7)0.5432 (3)0.057 (1)
N10.4035 (3)0.4375 (6)0.2882 (3)0.022 (1)
N20.5603 (3)0.2612 (7)0.2506 (3)0.020 (1)
N30.4264 (3)0.0603 (7)0.1549 (3)0.022 (1)
C10.3572 (4)0.5875 (8)0.3453 (3)0.025 (1)
C20.4124 (4)0.7332 (8)0.4113 (3)0.029 (1)
C30.5190 (4)0.7229 (9)0.4214 (4)0.034 (1)
C40.5679 (4)0.5686 (9)0.3678 (3)0.028 (1)
C50.5084 (4)0.4211 (8)0.3019 (4)0.023 (1)
C60.5255 (4)0.0780 (8)0.1893 (3)0.020 (1)
C70.5999 (4)0.0926 (9)0.1658 (4)0.024 (1)
C80.5697 (4)0.2822 (8)0.1074 (3)0.021 (1)
C90.4647 (4)0.3052 (8)0.0730 (3)0.020 (1)
C100.3969 (4)0.1298 (7)0.0969 (3)0.020 (1)
C110.1762 (4)0.3958 (8)0.0211 (4)0.021 (1)
C120.1335 (4)0.5323 (8)0.0994 (3)0.018 (1)
C130.0293 (4)0.4140 (9)0.1134 (4)0.019 (1)
C140.0147 (4)0.5021 (9)0.2006 (3)0.022 (1)
C150.1174 (3)0.3783 (9)0.2138 (3)0.027 (1)
C160.1492 (4)0.418 (1)0.3059 (4)0.038 (1)
H10.28520.59160.33960.029*
H20.37850.83680.44840.035*
H30.55760.82200.46510.040*
H40.63990.56070.37460.034*
H50.62640.27920.25830.025*
H60.66910.07540.19010.029*
H70.61800.39430.09070.025*
H80.44120.43610.03480.024*
H90.32760.14190.07230.024*
H100.12040.70280.07990.021*
H110.02110.45140.05920.023*
H120.02570.68000.19610.026*
H130.10650.20130.20800.033*
H140.09080.38810.35300.046*
H150.17080.58700.31130.046*
H160.01020.08190.10240.036*
H170.11640.45180.26820.039*
H180.18660.58570.12310.058*
H190.21050.13540.35050.059*
H200.22320.14200.21790.033*
H210.15550.07140.20350.033*
H220.19090.21420.46990.065*
H230.21370.06770.36790.065*
H240.05080.67050.36650.092*
H250.10310.88610.42530.092*
H260.08080.39540.55530.086*
H270.11200.56200.50220.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0128 (3)0.0194 (3)0.0253 (3)0.0012 (3)0.0032 (2)0.0011 (4)
O10.012 (2)0.020 (2)0.023 (2)0.007 (2)0.001 (1)0.006 (2)
O20.023 (2)0.024 (2)0.024 (2)0.005 (1)0.005 (2)0.003 (1)
O30.010 (2)0.021 (2)0.023 (2)0.001 (1)0.001 (2)0.000 (2)
O40.021 (2)0.012 (2)0.036 (3)0.002 (2)0.008 (2)0.004 (2)
O50.013 (2)0.037 (2)0.027 (2)0.001 (2)0.001 (2)0.001 (2)
O60.020 (2)0.042 (2)0.052 (3)0.001 (2)0.009 (2)0.015 (2)
O70.017 (2)0.060 (3)0.039 (2)0.010 (2)0.005 (2)0.022 (2)
O80.014 (2)0.017 (2)0.033 (2)0.001 (2)0.001 (2)0.003 (2)
O90.041 (3)0.048 (2)0.041 (2)0.002 (2)0.001 (2)0.003 (2)
O100.051 (3)0.085 (3)0.049 (3)0.018 (3)0.005 (2)0.025 (3)
O110.048 (3)0.064 (3)0.056 (3)0.001 (2)0.008 (2)0.010 (2)
N10.020 (2)0.019 (2)0.024 (3)0.003 (2)0.001 (2)0.002 (2)
N20.008 (2)0.024 (3)0.028 (2)0.001 (2)0.003 (2)0.001 (2)
N30.012 (2)0.022 (2)0.032 (3)0.000 (2)0.001 (2)0.005 (2)
C10.022 (3)0.023 (3)0.027 (3)0.003 (2)0.006 (2)0.000 (2)
C20.028 (3)0.028 (3)0.028 (3)0.007 (2)0.007 (2)0.006 (2)
C30.039 (4)0.032 (3)0.027 (3)0.003 (2)0.005 (3)0.010 (2)
C40.022 (3)0.036 (3)0.025 (3)0.004 (2)0.007 (2)0.001 (3)
C50.020 (3)0.022 (3)0.025 (3)0.006 (2)0.002 (2)0.001 (2)
C60.017 (3)0.015 (2)0.028 (3)0.000 (2)0.001 (2)0.006 (2)
C70.012 (3)0.033 (3)0.027 (3)0.004 (2)0.003 (2)0.010 (3)
C80.017 (3)0.019 (2)0.028 (3)0.003 (2)0.006 (2)0.003 (2)
C90.023 (3)0.019 (2)0.019 (3)0.004 (2)0.003 (2)0.005 (2)
C100.016 (3)0.020 (3)0.023 (3)0.002 (2)0.001 (2)0.005 (2)
C110.018 (3)0.017 (2)0.029 (3)0.003 (2)0.004 (3)0.003 (2)
C120.021 (3)0.008 (2)0.023 (3)0.002 (2)0.002 (2)0.001 (2)
C130.014 (3)0.015 (2)0.027 (3)0.003 (2)0.003 (3)0.001 (2)
C140.014 (3)0.024 (3)0.026 (3)0.002 (2)0.004 (2)0.003 (2)
C150.008 (3)0.036 (3)0.036 (3)0.002 (2)0.004 (2)0.006 (2)
C160.021 (3)0.050 (3)0.041 (4)0.013 (3)0.006 (3)0.010 (3)
Geometric parameters (Å, º) top
Cu1—O11.965 (3)N3—C61.327 (6)
Cu1—O31.932 (3)N3—C101.358 (6)
Cu1—O82.342 (3)C1—C21.375 (7)
Cu1—N12.015 (4)C1—H10.9301
Cu1—N31.985 (4)C2—C31.377 (8)
O1—C111.271 (6)C2—H20.9300
O2—C111.259 (6)C3—C41.359 (7)
O3—C121.417 (5)C3—H30.9300
O4—C131.442 (6)C4—C51.404 (7)
O4—H160.8200C4—H40.9300
O5—C141.437 (6)C6—C71.415 (7)
O5—H170.8200C7—C81.362 (7)
O6—C151.437 (6)C7—H60.9300
O6—H180.8200C8—C91.401 (7)
O7—C161.447 (7)C8—H70.9300
O7—H190.8199C9—C101.375 (7)
O8—H200.8884C9—H80.9300
O8—H210.9224C10—H90.9300
O9—H220.9041C11—C121.522 (7)
O9—H230.9637C12—C131.538 (7)
O10—H241.0013C12—H100.9800
O10—H250.9129C13—C141.531 (8)
O11—H260.9455C13—H110.9800
O11—H270.9280C14—C151.531 (7)
N1—C11.360 (6)C14—H120.9800
N1—C51.357 (6)C15—C161.464 (8)
N2—C51.377 (6)C15—H130.9800
N2—C61.374 (6)C16—H140.9699
N2—H50.8601C16—H150.9700
Cu1···N23.221 (4)C1···H202.7946
Cu1···C12.919 (5)C1···H233.4299
Cu1···C52.975 (5)C1···H233.2546
Cu1···C62.956 (5)C2···O93.310 (6)
Cu1···C93.326 (5)C2···C42.372 (8)
Cu1···C102.862 (4)C2···C52.736 (7)
Cu1···C103.482 (4)C2···H11.9959
Cu1···C112.742 (5)C2···H32.0091
Cu1···C122.792 (5)C2···H32.8651
Cu1···H12.9459C2···H43.2147
Cu1···H83.0842C2···H203.5564
Cu1···H92.8530C2···H233.1610
Cu1···H93.3697C3···C52.382 (7)
Cu1···H103.5037C3···H13.2035
Cu1···H173.2086C3···H22.0163
Cu1···H202.8312C3···H23.0213
Cu1···H203.3502C3···H32.9826
Cu1···H212.5433C3···H41.9981
Cu1···H233.5200C4···O73.239 (6)
O1···O22.219 (4)C4···C73.534 (7)
O1···O32.619 (5)C4···H23.2132
O1···O43.221 (5)C4···H22.9542
O1···O63.238 (5)C4···H31.9929
O1···O83.311 (5)C4···H33.3727
O1···N32.803 (5)C4···H52.4285
O1···C83.304 (6)C4···H153.5997
O1···C93.466 (6)C5···O73.454 (6)
O1···C102.899 (5)C5···C62.511 (7)
O1···C122.382 (6)C5···C73.597 (7)
O1···C133.389 (6)C5···C83.435 (7)
O1···H72.8090C5···H13.1643
O1···H82.8222C5···H33.2267
O1···H92.4792C5···H42.0396
O1···H93.2766C5···H51.8984
O1···H103.0307C6···O73.590 (6)
O1···H182.6885C6···C82.403 (7)
O1···H203.5179C6···C92.739 (6)
O1···H213.0808C6···C102.304 (6)
O2···O33.596 (5)C6···H51.8956
O2···O43.210 (5)C6···H62.0458
O2···O42.693 (5)C6···H73.2495
O2···O62.908 (5)C6···H73.4933
O2···O63.374 (5)C6···H83.5519
O2···C122.422 (6)C6···H83.3383
O2···C132.971 (7)C6···H93.1376
O2···C133.361 (6)C7···O73.483 (6)
O2···C133.515 (6)C7···C43.534 (7)
O2···C143.193 (6)C7···C53.597 (7)
O2···C153.591 (6)C7···C92.377 (7)
O2···C153.440 (6)C7···C102.710 (7)
O2···H63.4404C7···H43.5535
O2···H102.6399C7···H52.4310
O2···H103.3802C7···H72.0025
O2···H112.7771C7···H83.2212
O2···H112.7960C7···H83.0162
O2···H113.3302C7···H183.4085
O2···H122.5314C8···O13.304 (6)
O2···H132.7036C8···O63.358 (6)
O2···H163.5798C8···N23.255 (6)
O2···H161.8765C8···C53.435 (7)
O2···H182.1117C8···C102.384 (7)
O3···O43.005 (5)C8···C103.592 (7)
O3···O52.606 (5)C8···H53.2624
O3···O82.957 (4)C8···H61.9973
O3···O82.723 (4)C8···H82.0395
O3···N12.880 (5)C8···H82.7858
O3···C12.908 (6)C8···H93.2199
O3···C103.442 (6)C8···H183.2313
O3···C112.426 (6)C9···Cu13.326 (5)
O3···C132.466 (6)C9···O13.466 (6)
O3···C142.922 (6)C9···N23.600 (6)
O3···H12.4190C9···H63.2229
O3···H92.9659C9···H72.0382
O3···H101.9583C9···H73.3408
O3···H113.2730C9···H82.9121
O3···H123.1487C9···H91.9926
O3···H171.8746C10···Cu13.482 (4)
O3···H201.8534C10···O33.442 (6)
O3···H212.6283C10···C83.592 (7)
O3···H213.0298C10···H73.2295
O4···O22.693 (5)C10···H72.9953
O4···O52.873 (5)C10···H82.0158
O4···O63.586 (5)C10···H83.1998
O4···O82.740 (5)C10···H203.0361
O4···C112.694 (6)C11···O43.582 (6)
O4···C113.582 (6)C11···O63.427 (6)
O4···C123.587 (5)C11···C132.474 (8)
O4···C122.401 (5)C11···H83.5504
O4···C142.435 (6)C11···H93.5549
O4···C152.949 (6)C11···H93.2250
O4···H102.7179C11···H102.0518
O4···H103.2255C11···H112.7118
O4···H103.3725C11···H113.2699
O4···H111.9844C11···H163.3067
O4···H112.7726C11···H162.8152
O4···H123.0036C11···H182.7068
O4···H123.2681C11···H213.2234
O4···H132.5189C12···O43.587 (5)
O4···H172.7900C12···O83.372 (5)
O4···H203.0319C12···C142.574 (7)
O4···H211.8304C12···H93.1528
O5···O83.275 (5)C12···H112.0697
O5···O93.397 (5)C12···H113.4342
O5···O102.722 (6)C12···H122.7660
O5···C122.979 (6)C12···H163.0883
O5···C132.435 (7)C12···H163.5328
O5···C152.392 (5)C12···H163.1686
O5···C162.758 (7)C12···H172.5272
O5···H13.0758C12···H202.6375
O5···H103.4332C12···H212.9251
O5···H113.2644C12···H213.2980
O5···H121.9824C13···O23.515 (6)
O5···H132.6374C13···O23.361 (6)
O5···H142.3242C13···C152.553 (8)
O5···H153.1409C13···H102.0659
O5···H163.3183C13···H103.4060
O5···H203.3113C13···H113.5462
O5···H212.7520C13···H122.0664
O5···H223.3059C13···H132.6406
O5···H233.0679C13···H161.8817
O5···H241.7255C13···H163.2443
O5···H253.1623C13···H172.3935
O5···H273.2448C13···H182.9819
O6···O13.238 (5)C13···H212.7098
O6···O23.374 (5)C14···O23.193 (6)
O6···O22.908 (5)C14···C162.509 (8)
O6···O72.913 (6)C14···H102.8550
O6···C83.358 (6)C14···H112.0637
O6···C113.427 (6)C14···H132.0394
O6···C133.025 (7)C14···H142.6128
O6···C142.442 (6)C14···H152.7862
O6···C162.410 (6)C14···H162.7011
O6···H53.1697C14···H163.4684
O6···H63.4545C14···H171.8767
O6···H63.2697C14···H182.4167
O6···H72.5763C14···H213.2232
O6···H93.3629C14···H242.6171
O6···H112.7057C15···O23.440 (6)
O6···H122.6072C15···O23.591 (6)
O6···H131.9559C15···H53.5180
O6···H143.2343C15···H112.7376
O6···H152.5808C15···H122.0663
O6···H163.2370C15···H142.0076
O6···H193.5122C15···H152.0077
O7···O112.716 (5)C15···H162.7835
O7···N22.747 (5)C15···H173.0711
O7···C43.239 (6)C15···H181.8767
O7···C53.454 (6)C15···H192.7876
O7···C63.590 (6)C15···H243.3173
O7···C73.483 (6)C16···O113.358 (7)
O7···C152.397 (6)C16···H43.1371
O7···H42.5316C16···H53.0101
O7···H51.9339C16···H122.7959
O7···H62.8021C16···H131.9801
O7···H132.4903C16···H173.5728
O7···H141.9922C16···H182.7909
O7···H151.9922C16···H191.8856
O7···H183.5073C16···H242.9770
O7···H263.1821C16···H263.5348
O7···H273.0297C16···H263.3415
O8···O32.723 (4)C16···H273.3786
O8···O92.890 (5)H1···O82.8130
O8···N13.392 (5)H1···O93.2580
O8···N33.147 (6)H2···O92.5615
O8···C13.235 (6)H2···C33.0213
O8···C103.401 (6)H2···C42.9542
O8···C123.372 (5)H3···O93.3874
O8···C123.557 (5)H3···C13.1804
O8···C133.576 (6)H3···C22.8651
O8···H12.8130H3···C32.9826
O8···H13.5650H3···C43.3727
O8···H93.0759H4···O72.5316
O8···H102.9708H4···O93.1807
O8···H123.5969H4···O113.5765
O8···H163.3322H4···C73.5535
O8···H173.3565H4···C163.1371
O8···H172.7878H5···O63.1697
O8···H231.9267H5···O71.9339
O8···H243.5438H5···C83.2624
O8···H253.3268H5···C153.5180
O9···O102.737 (6)H5···C163.0101
O9···O112.713 (6)H6···O23.4404
O9···C13.595 (6)H6···O63.2697
O9···C23.310 (6)H6···O63.4545
O9···H13.2580H6···O72.8021
O9···H13.2161H7···O12.8090
O9···H22.5615H7···O62.5763
O9···H33.3874H7···N23.1508
O9···H43.1807H7···N33.5474
O9···H173.2114H7···C63.4933
O9···H203.4046H7···C93.3408
O9···H213.3285H7···C102.9953
O9···H243.2014H8···Cu13.0842
O9···H251.8241H8···O12.8222
O9···H263.0879H8···N33.2695
O9···H273.3957H8···N33.4306
O9···H273.0828H8···C63.5519
O10···O92.737 (6)H8···C63.3383
O10···O112.729 (6)H8···C73.0162
O10···O112.807 (6)H8···C82.7858
O10···C143.546 (6)H8···C92.9121
O10···C163.495 (7)H8···C103.1998
O10···H13.5959H8···C113.5504
O10···H123.3336H9···Cu13.3697
O10···H142.8928H9···O13.2766
O10···H143.3050H9···O32.9659
O10···H153.2588H9···O63.3629
O10···H173.0740H9···C113.2250
O10···H223.0310H9···C123.1528
O10···H232.8483H10···O23.3802
O10···H262.8579H10···O42.7179
O10···H261.8613H10···O43.3725
O10···H271.8015H10···O82.9708
O10···H272.9174H10···C133.4060
O11···O72.716 (5)H11···O23.3302
O11···O102.807 (6)H11···O22.7960
O11···C163.358 (7)H11···O42.7726
O11···H43.5765H11···C113.2699
O11···H143.5284H11···C123.4342
O11···H142.9618H11···C133.5462
O11···H152.8813H12···O22.5314
O11···H191.9401H12···O43.0036
O11···H221.8087H12···O83.5969
O11···H233.4850H13···O22.7036
O11···H242.9599H14···O103.3050
O11···H243.3927H14···O112.9618
O11···H253.5273H14···O113.5284
O11···H252.9401H15···O112.8813
O11···H253.3591H15···C43.5997
N1···N22.380 (6)H16···O21.8765
N1···N32.864 (5)H16···C112.8152
N1···C22.399 (6)H16···C123.5328
N1···C32.771 (6)H16···C123.1686
N1···C42.407 (6)H16···C133.2443
N1···C63.000 (6)H16···C143.4684
N1···H11.9822H17···O83.3565
N1···H23.2323H18···O12.6885
N1···H43.2408H18···O22.1117
N1···H53.1095H18···C73.4085
N1···H203.3443H18···C83.2313
N1···H233.4976H18···C112.7068
N2···O72.747 (5)H19···O111.9401
N2···N32.355 (5)H19···N23.2205
N2···C42.380 (6)H20···Cu13.3502
N2···C72.379 (6)H20···O31.8534
N2···C83.255 (6)H20···O53.3113
N2···C93.600 (6)H20···N13.3443
N2···C103.581 (6)H20···C12.7946
N2···H42.5500H20···C23.5564
N2···H62.5413H20···C122.6375
N2···H73.1508H21···O33.0298
N2···H193.2205H21···C123.2980
N3···C52.996 (6)H22···O103.0310
N3···C72.393 (6)H23···O102.8483
N3···C82.787 (6)H23···C13.2546
N3···C92.404 (6)H23···C23.1610
N3···H53.0758H24···O83.5438
N3···H63.2217H24···O93.2014
N3···H73.5474H24···O113.3927
N3···H83.2368H25···O83.3268
N3···H83.2695H25···O91.8241
N3···H83.4306H25···O113.5273
N3···H91.9776H25···O113.3591
N3···H203.1085H26···O73.1821
C1···O83.235 (6)H26···O101.8613
C1···C32.368 (7)H26···C163.3415
C1···C42.723 (8)H26···C163.5348
C1···C52.327 (7)H27···O73.0297
C1···H22.0143H27···O93.3957
C1···H33.2102H27···O102.9174
C1···H33.1804H27···C163.3786
C1···H173.2744
O1—Cu1—O384.5 (1)H4—C4—C3120.4348
O1—Cu1—O8100.1 (1)C7—C6—N2117.1 (4)
O1—Cu1—N1157.7 (2)C7—C6—N3121.6 (4)
O1—Cu1—N390.4 (1)C8—C7—C6119.8 (4)
O3—Cu1—O887.0 (1)C8—C7—H6120.0782
O3—Cu1—N193.7 (1)H6—C7—C6120.0856
O3—Cu1—N3174.8 (1)C9—C8—C7118.7 (4)
O8—Cu1—N1102.0 (1)C9—C8—H7120.6486
O8—Cu1—N392.9 (1)H7—C8—C7120.6357
N1—Cu1—N391.4 (2)C10—C9—C8118.4 (4)
C11—O1—Cu1114.1 (3)C10—C9—H8120.7934
C12—O3—Cu1112.1 (3)H8—C9—C8120.7838
C13—O4—H16109.4706H9—C10—N3118.3881
C14—O5—H17109.4708H9—C10—C9118.3995
C15—O6—H18109.4720C12—C11—O1116.7 (4)
C16—O7—H19109.4672C12—C11—O2120.8 (4)
H20—O8—Cu1114.7330C13—C12—O3113.1 (4)
H20—O8—H21107.2020C13—C12—C11107.8 (4)
H21—O8—Cu191.7466C13—C12—H10108.1967
H22—O9—H23137.4809H10—C12—O3108.1899
H24—O10—H25108.6787H10—C12—C11108.1980
H26—O11—H2786.9886C14—C13—C12114.0 (4)
C1—N1—Cu1118.4 (3)C14—C13—O4109.9 (4)
C1—N1—C5117.8 (4)C14—C13—H11108.5173
C5—N1—Cu1122.6 (3)H11—C13—C12108.5054
C5—N2—C6131.8 (4)H11—C13—O4108.5133
C5—N2—H5114.1157C15—C14—C13113.0 (4)
C6—N2—H5114.1174C15—C14—O5107.4 (4)
C6—N3—Cu1125.2 (3)C15—C14—H12108.7439
C6—N3—C10118.2 (4)H12—C14—C13108.7483
C10—N3—Cu1116.5 (3)H12—C14—O5108.7468
C2—C1—N1122.6 (5)C16—C15—C14113.8 (4)
C2—C1—H1118.7117C16—C15—O6112.3 (4)
H1—C1—N1118.7003C16—C15—H13106.5353
C3—C2—C1118.8 (5)H13—C15—C14106.5292
C3—C2—H2120.6150H13—C15—O6106.5240
H2—C2—C1120.6134H14—C16—C15109.4594
C4—C3—C2120.2 (5)H14—C16—H15108.0508
C4—C3—H3119.8925H14—C16—O7109.4700
H3—C3—C2119.8751H15—C16—C15109.4633
C5—C4—C3119.1 (5)H15—C16—O7109.4644
C5—C4—H4120.4492
O3—Cu1—O1—C116.3 (3)N1—C1—C2—C31.5 (7)
O1—Cu1—O3—C1210.7 (3)C1—C2—C3—C40.9 (7)
O1—Cu1—O8—H2063.8C2—C3—C4—C50.3 (6)
O1—Cu1—N1—C198.9 (4)C3—C4—C5—N12.8 (7)
O1—Cu1—N3—C6136.6 (4)C3—C4—C5—N2178.0 (4)
Cu1—O1—C11—O2178.6 (4)N2—C6—C7—C8178.2 (5)
Cu1—O3—C12—C1112.8 (4)C6—C7—C8—C90.9 (7)
H16—O4—C13—C12155.4C7—C8—C9—C102.4 (7)
H17—O5—C14—C1328.9C8—C9—C10—N32.3 (7)
H18—O6—C15—C1432.3O1—C11—C12—O38.2 (6)
H19—O7—C16—C1597.5O2—C11—C12—O3172.7 (4)
Cu1—N1—C1—C2164.0 (4)O3—C12—C13—O475.2 (5)
Cu1—N1—C5—N216.3 (6)C11—C12—C13—O448.2 (5)
Cu1—N1—C5—C4162.8 (4)O4—C13—C14—O561.5 (5)
C6—N2—C5—N18.7 (8)C12—C13—C14—O558.9 (5)
C6—N2—C5—C4172.1 (4)O5—C14—C15—O6173.2 (4)
C5—N2—C6—N314.4 (8)C13—C14—C15—O665.2 (5)
Cu1—N3—C6—N26.6 (7)O6—C15—C16—O765.6 (5)
Cu1—N3—C10—C9176.3 (4)C14—C15—C16—O7167.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H16···O2i0.821.882.693 (6)173
O5—H17···O30.821.872.606 (5)148
O6—H18···O2ii0.822.112.908 (5)164
O7—H19···O11iii0.821.942.716 (6)158
O8—H20···O3iv0.891.852.723 (5)166
O8—H21···O40.921.832.740 (6)168
O9—H22···O110.901.812.713 (6)180
O9—H23···O80.961.932.890 (6)180
O10—H24···O51.001.732.722 (6)173
O10—H25···O9v0.911.822.737 (6)180
O11—H26···O10iii0.951.862.807 (6)179
O11—H27···O100.931.802.729 (7)178
N2—H5···O7vi0.861.932.747 (6)157
Symmetry codes: (i) x, y1/2, z; (ii) x, y+1/2, z; (iii) x, y1/2, z+1; (iv) x, y1, z; (v) x, y+1, z; (vi) x+1, y, z.
 

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