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
CCDC reference: 621510
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (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
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)]·3H2O | F(000) = 522.00 |
Mr = 500.96 | Dx = 1.629 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: P 2yb | Cell parameters from 7711 reflections |
a = 13.02 (1) Å | θ = 3.1–27.5° |
b = 5.447 (5) Å | µ = 1.14 mm−1 |
c = 14.52 (1) Å | T = 123 K |
β = 97.34 (4)° | Needle, light-blue |
V = 1021.3 (14) Å3 | 0.40 × 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-1 | Rint = 0.074 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −16→16 |
Tmin = 0.576, Tmax = 0.989 | k = −7→6 |
10058 measured reflections | l = −18→18 |
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) = 0.086 | Δρmax = 0.58 e Å−3 |
S = 0.85 | Δρmin = −0.55 e Å−3 |
4365 reflections | Absolute structure: Flack (1983), 1792 Friedel pairs |
294 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.31756 (4) | 0.3039 (1) | 0.17393 (4) | 0.0197 (1) | |
O1 | 0.2609 (2) | 0.2807 (7) | 0.0422 (2) | 0.0187 (7) | |
O2 | 0.1282 (3) | 0.3962 (5) | −0.0599 (2) | 0.0240 (8) | |
O3 | 0.2056 (3) | 0.5331 (5) | 0.1812 (2) | 0.0181 (8) | |
O4 | 0.0451 (3) | 0.1520 (6) | 0.1178 (3) | 0.024 (1) | |
O5 | 0.0572 (3) | 0.4507 (6) | 0.2819 (2) | 0.0258 (8) | |
O6 | −0.1970 (3) | 0.4455 (6) | 0.1403 (3) | 0.039 (1) | |
O7 | −0.2335 (3) | 0.2558 (7) | 0.3209 (3) | 0.039 (1) | |
O8 | 0.2150 (3) | 0.0107 (6) | 0.2371 (3) | 0.0218 (8) | |
O9 | 0.2130 (3) | 0.0962 (7) | 0.4333 (3) | 0.044 (1) | |
O10 | 0.0481 (3) | 0.781 (1) | 0.4213 (3) | 0.061 (1) | |
O11 | 0.1467 (3) | 0.4501 (7) | 0.5432 (3) | 0.057 (1) | |
N1 | 0.4035 (3) | 0.4375 (6) | 0.2882 (3) | 0.022 (1) | |
N2 | 0.5603 (3) | 0.2612 (7) | 0.2506 (3) | 0.020 (1) | |
N3 | 0.4264 (3) | 0.0603 (7) | 0.1549 (3) | 0.022 (1) | |
C1 | 0.3572 (4) | 0.5875 (8) | 0.3453 (3) | 0.025 (1) | |
C2 | 0.4124 (4) | 0.7332 (8) | 0.4113 (3) | 0.029 (1) | |
C3 | 0.5190 (4) | 0.7229 (9) | 0.4214 (4) | 0.034 (1) | |
C4 | 0.5679 (4) | 0.5686 (9) | 0.3678 (3) | 0.028 (1) | |
C5 | 0.5084 (4) | 0.4211 (8) | 0.3019 (4) | 0.023 (1) | |
C6 | 0.5255 (4) | 0.0780 (8) | 0.1893 (3) | 0.020 (1) | |
C7 | 0.5999 (4) | −0.0926 (9) | 0.1658 (4) | 0.024 (1) | |
C8 | 0.5697 (4) | −0.2822 (8) | 0.1074 (3) | 0.021 (1) | |
C9 | 0.4647 (4) | −0.3052 (8) | 0.0730 (3) | 0.020 (1) | |
C10 | 0.3969 (4) | −0.1298 (7) | 0.0969 (3) | 0.020 (1) | |
C11 | 0.1762 (4) | 0.3958 (8) | 0.0211 (4) | 0.021 (1) | |
C12 | 0.1335 (4) | 0.5323 (8) | 0.0994 (3) | 0.018 (1) | |
C13 | 0.0293 (4) | 0.4140 (9) | 0.1134 (4) | 0.019 (1) | |
C14 | −0.0147 (4) | 0.5021 (9) | 0.2006 (3) | 0.022 (1) | |
C15 | −0.1174 (3) | 0.3783 (9) | 0.2138 (3) | 0.027 (1) | |
C16 | −0.1492 (4) | 0.418 (1) | 0.3059 (4) | 0.038 (1) | |
H1 | 0.2852 | 0.5916 | 0.3396 | 0.029* | |
H2 | 0.3785 | 0.8368 | 0.4484 | 0.035* | |
H3 | 0.5576 | 0.8220 | 0.4651 | 0.040* | |
H4 | 0.6399 | 0.5607 | 0.3746 | 0.034* | |
H5 | 0.6264 | 0.2792 | 0.2583 | 0.025* | |
H6 | 0.6691 | −0.0754 | 0.1901 | 0.029* | |
H7 | 0.6180 | −0.3943 | 0.0907 | 0.025* | |
H8 | 0.4412 | −0.4361 | 0.0348 | 0.024* | |
H9 | 0.3276 | −0.1419 | 0.0723 | 0.024* | |
H10 | 0.1204 | 0.7028 | 0.0799 | 0.021* | |
H11 | −0.0211 | 0.4514 | 0.0592 | 0.023* | |
H12 | −0.0257 | 0.6800 | 0.1961 | 0.026* | |
H13 | −0.1065 | 0.2013 | 0.2080 | 0.033* | |
H14 | −0.0908 | 0.3881 | 0.3530 | 0.046* | |
H15 | −0.1708 | 0.5870 | 0.3113 | 0.046* | |
H16 | −0.0102 | 0.0819 | 0.1024 | 0.036* | |
H17 | 0.1164 | 0.4518 | 0.2682 | 0.039* | |
H18 | −0.1866 | 0.5857 | 0.1231 | 0.058* | |
H19 | −0.2105 | 0.1354 | 0.3505 | 0.059* | |
H20 | 0.2232 | −0.1420 | 0.2179 | 0.033* | |
H21 | 0.1555 | 0.0714 | 0.2035 | 0.033* | |
H22 | 0.1909 | 0.2142 | 0.4699 | 0.065* | |
H23 | 0.2137 | 0.0677 | 0.3679 | 0.065* | |
H24 | 0.0508 | 0.6705 | 0.3665 | 0.092* | |
H25 | 0.1031 | 0.8861 | 0.4253 | 0.092* | |
H26 | 0.0808 | 0.3954 | 0.5553 | 0.086* | |
H27 | 0.1120 | 0.5620 | 0.5022 | 0.086* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0128 (3) | 0.0194 (3) | 0.0253 (3) | 0.0012 (3) | −0.0032 (2) | −0.0011 (4) |
O1 | 0.012 (2) | 0.020 (2) | 0.023 (2) | 0.007 (2) | −0.001 (1) | −0.006 (2) |
O2 | 0.023 (2) | 0.024 (2) | 0.024 (2) | 0.005 (1) | −0.005 (2) | −0.003 (1) |
O3 | 0.010 (2) | 0.021 (2) | 0.023 (2) | −0.001 (1) | −0.001 (2) | 0.000 (2) |
O4 | 0.021 (2) | 0.012 (2) | 0.036 (3) | −0.002 (2) | −0.008 (2) | −0.004 (2) |
O5 | 0.013 (2) | 0.037 (2) | 0.027 (2) | −0.001 (2) | 0.001 (2) | 0.001 (2) |
O6 | 0.020 (2) | 0.042 (2) | 0.052 (3) | −0.001 (2) | −0.009 (2) | 0.015 (2) |
O7 | 0.017 (2) | 0.060 (3) | 0.039 (2) | −0.010 (2) | −0.005 (2) | 0.022 (2) |
O8 | 0.014 (2) | 0.017 (2) | 0.033 (2) | 0.001 (2) | −0.001 (2) | −0.003 (2) |
O9 | 0.041 (3) | 0.048 (2) | 0.041 (2) | 0.002 (2) | 0.001 (2) | −0.003 (2) |
O10 | 0.051 (3) | 0.085 (3) | 0.049 (3) | −0.018 (3) | 0.005 (2) | −0.025 (3) |
O11 | 0.048 (3) | 0.064 (3) | 0.056 (3) | −0.001 (2) | −0.008 (2) | 0.010 (2) |
N1 | 0.020 (2) | 0.019 (2) | 0.024 (3) | 0.003 (2) | −0.001 (2) | −0.002 (2) |
N2 | 0.008 (2) | 0.024 (3) | 0.028 (2) | −0.001 (2) | −0.003 (2) | −0.001 (2) |
N3 | 0.012 (2) | 0.022 (2) | 0.032 (3) | −0.000 (2) | 0.001 (2) | 0.005 (2) |
C1 | 0.022 (3) | 0.023 (3) | 0.027 (3) | 0.003 (2) | −0.006 (2) | 0.000 (2) |
C2 | 0.028 (3) | 0.028 (3) | 0.028 (3) | 0.007 (2) | −0.007 (2) | −0.006 (2) |
C3 | 0.039 (4) | 0.032 (3) | 0.027 (3) | −0.003 (2) | −0.005 (3) | −0.010 (2) |
C4 | 0.022 (3) | 0.036 (3) | 0.025 (3) | −0.004 (2) | −0.007 (2) | 0.001 (3) |
C5 | 0.020 (3) | 0.022 (3) | 0.025 (3) | −0.006 (2) | −0.002 (2) | −0.001 (2) |
C6 | 0.017 (3) | 0.015 (2) | 0.028 (3) | 0.000 (2) | 0.001 (2) | 0.006 (2) |
C7 | 0.012 (3) | 0.033 (3) | 0.027 (3) | 0.004 (2) | −0.003 (2) | 0.010 (3) |
C8 | 0.017 (3) | 0.019 (2) | 0.028 (3) | 0.003 (2) | 0.006 (2) | 0.003 (2) |
C9 | 0.023 (3) | 0.019 (2) | 0.019 (3) | −0.004 (2) | 0.003 (2) | 0.005 (2) |
C10 | 0.016 (3) | 0.020 (3) | 0.023 (3) | −0.002 (2) | 0.001 (2) | 0.005 (2) |
C11 | 0.018 (3) | 0.017 (2) | 0.029 (3) | −0.003 (2) | 0.004 (3) | 0.003 (2) |
C12 | 0.021 (3) | 0.008 (2) | 0.023 (3) | 0.002 (2) | −0.002 (2) | 0.001 (2) |
C13 | 0.014 (3) | 0.015 (2) | 0.027 (3) | 0.003 (2) | −0.003 (3) | −0.001 (2) |
C14 | 0.014 (3) | 0.024 (3) | 0.026 (3) | −0.002 (2) | −0.004 (2) | 0.003 (2) |
C15 | 0.008 (3) | 0.036 (3) | 0.036 (3) | 0.002 (2) | −0.004 (2) | 0.006 (2) |
C16 | 0.021 (3) | 0.050 (3) | 0.041 (4) | −0.013 (3) | −0.006 (3) | 0.010 (3) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.965 (3) | N3—C6 | 1.327 (6) |
Cu1—O3 | 1.932 (3) | N3—C10 | 1.358 (6) |
Cu1—O8 | 2.342 (3) | C1—C2 | 1.375 (7) |
Cu1—N1 | 2.015 (4) | C1—H1 | 0.9301 |
Cu1—N3 | 1.985 (4) | C2—C3 | 1.377 (8) |
O1—C11 | 1.271 (6) | C2—H2 | 0.9300 |
O2—C11 | 1.259 (6) | C3—C4 | 1.359 (7) |
O3—C12 | 1.417 (5) | C3—H3 | 0.9300 |
O4—C13 | 1.442 (6) | C4—C5 | 1.404 (7) |
O4—H16 | 0.8200 | C4—H4 | 0.9300 |
O5—C14 | 1.437 (6) | C6—C7 | 1.415 (7) |
O5—H17 | 0.8200 | C7—C8 | 1.362 (7) |
O6—C15 | 1.437 (6) | C7—H6 | 0.9300 |
O6—H18 | 0.8200 | C8—C9 | 1.401 (7) |
O7—C16 | 1.447 (7) | C8—H7 | 0.9300 |
O7—H19 | 0.8199 | C9—C10 | 1.375 (7) |
O8—H20 | 0.8884 | C9—H8 | 0.9300 |
O8—H21 | 0.9224 | C10—H9 | 0.9300 |
O9—H22 | 0.9041 | C11—C12 | 1.522 (7) |
O9—H23 | 0.9637 | C12—C13 | 1.538 (7) |
O10—H24 | 1.0013 | C12—H10 | 0.9800 |
O10—H25 | 0.9129 | C13—C14 | 1.531 (8) |
O11—H26 | 0.9455 | C13—H11 | 0.9800 |
O11—H27 | 0.9280 | C14—C15 | 1.531 (7) |
N1—C1 | 1.360 (6) | C14—H12 | 0.9800 |
N1—C5 | 1.357 (6) | C15—C16 | 1.464 (8) |
N2—C5 | 1.377 (6) | C15—H13 | 0.9800 |
N2—C6 | 1.374 (6) | C16—H14 | 0.9699 |
N2—H5 | 0.8601 | C16—H15 | 0.9700 |
| | | |
Cu1···N2 | 3.221 (4) | C1···H20 | 2.7946 |
Cu1···C1 | 2.919 (5) | C1···H23 | 3.4299 |
Cu1···C5 | 2.975 (5) | C1···H23 | 3.2546 |
Cu1···C6 | 2.956 (5) | C2···O9 | 3.310 (6) |
Cu1···C9 | 3.326 (5) | C2···C4 | 2.372 (8) |
Cu1···C10 | 2.862 (4) | C2···C5 | 2.736 (7) |
Cu1···C10 | 3.482 (4) | C2···H1 | 1.9959 |
Cu1···C11 | 2.742 (5) | C2···H3 | 2.0091 |
Cu1···C12 | 2.792 (5) | C2···H3 | 2.8651 |
Cu1···H1 | 2.9459 | C2···H4 | 3.2147 |
Cu1···H8 | 3.0842 | C2···H20 | 3.5564 |
Cu1···H9 | 2.8530 | C2···H23 | 3.1610 |
Cu1···H9 | 3.3697 | C3···C5 | 2.382 (7) |
Cu1···H10 | 3.5037 | C3···H1 | 3.2035 |
Cu1···H17 | 3.2086 | C3···H2 | 2.0163 |
Cu1···H20 | 2.8312 | C3···H2 | 3.0213 |
Cu1···H20 | 3.3502 | C3···H3 | 2.9826 |
Cu1···H21 | 2.5433 | C3···H4 | 1.9981 |
Cu1···H23 | 3.5200 | C4···O7 | 3.239 (6) |
O1···O2 | 2.219 (4) | C4···C7 | 3.534 (7) |
O1···O3 | 2.619 (5) | C4···H2 | 3.2132 |
O1···O4 | 3.221 (5) | C4···H2 | 2.9542 |
O1···O6 | 3.238 (5) | C4···H3 | 1.9929 |
O1···O8 | 3.311 (5) | C4···H3 | 3.3727 |
O1···N3 | 2.803 (5) | C4···H5 | 2.4285 |
O1···C8 | 3.304 (6) | C4···H15 | 3.5997 |
O1···C9 | 3.466 (6) | C5···O7 | 3.454 (6) |
O1···C10 | 2.899 (5) | C5···C6 | 2.511 (7) |
O1···C12 | 2.382 (6) | C5···C7 | 3.597 (7) |
O1···C13 | 3.389 (6) | C5···C8 | 3.435 (7) |
O1···H7 | 2.8090 | C5···H1 | 3.1643 |
O1···H8 | 2.8222 | C5···H3 | 3.2267 |
O1···H9 | 2.4792 | C5···H4 | 2.0396 |
O1···H9 | 3.2766 | C5···H5 | 1.8984 |
O1···H10 | 3.0307 | C6···O7 | 3.590 (6) |
O1···H18 | 2.6885 | C6···C8 | 2.403 (7) |
O1···H20 | 3.5179 | C6···C9 | 2.739 (6) |
O1···H21 | 3.0808 | C6···C10 | 2.304 (6) |
O2···O3 | 3.596 (5) | C6···H5 | 1.8956 |
O2···O4 | 3.210 (5) | C6···H6 | 2.0458 |
O2···O4 | 2.693 (5) | C6···H7 | 3.2495 |
O2···O6 | 2.908 (5) | C6···H7 | 3.4933 |
O2···O6 | 3.374 (5) | C6···H8 | 3.5519 |
O2···C12 | 2.422 (6) | C6···H8 | 3.3383 |
O2···C13 | 2.971 (7) | C6···H9 | 3.1376 |
O2···C13 | 3.361 (6) | C7···O7 | 3.483 (6) |
O2···C13 | 3.515 (6) | C7···C4 | 3.534 (7) |
O2···C14 | 3.193 (6) | C7···C5 | 3.597 (7) |
O2···C15 | 3.591 (6) | C7···C9 | 2.377 (7) |
O2···C15 | 3.440 (6) | C7···C10 | 2.710 (7) |
O2···H6 | 3.4404 | C7···H4 | 3.5535 |
O2···H10 | 2.6399 | C7···H5 | 2.4310 |
O2···H10 | 3.3802 | C7···H7 | 2.0025 |
O2···H11 | 2.7771 | C7···H8 | 3.2212 |
O2···H11 | 2.7960 | C7···H8 | 3.0162 |
O2···H11 | 3.3302 | C7···H18 | 3.4085 |
O2···H12 | 2.5314 | C8···O1 | 3.304 (6) |
O2···H13 | 2.7036 | C8···O6 | 3.358 (6) |
O2···H16 | 3.5798 | C8···N2 | 3.255 (6) |
O2···H16 | 1.8765 | C8···C5 | 3.435 (7) |
O2···H18 | 2.1117 | C8···C10 | 2.384 (7) |
O3···O4 | 3.005 (5) | C8···C10 | 3.592 (7) |
O3···O5 | 2.606 (5) | C8···H5 | 3.2624 |
O3···O8 | 2.957 (4) | C8···H6 | 1.9973 |
O3···O8 | 2.723 (4) | C8···H8 | 2.0395 |
O3···N1 | 2.880 (5) | C8···H8 | 2.7858 |
O3···C1 | 2.908 (6) | C8···H9 | 3.2199 |
O3···C10 | 3.442 (6) | C8···H18 | 3.2313 |
O3···C11 | 2.426 (6) | C9···Cu1 | 3.326 (5) |
O3···C13 | 2.466 (6) | C9···O1 | 3.466 (6) |
O3···C14 | 2.922 (6) | C9···N2 | 3.600 (6) |
O3···H1 | 2.4190 | C9···H6 | 3.2229 |
O3···H9 | 2.9659 | C9···H7 | 2.0382 |
O3···H10 | 1.9583 | C9···H7 | 3.3408 |
O3···H11 | 3.2730 | C9···H8 | 2.9121 |
O3···H12 | 3.1487 | C9···H9 | 1.9926 |
O3···H17 | 1.8746 | C10···Cu1 | 3.482 (4) |
O3···H20 | 1.8534 | C10···O3 | 3.442 (6) |
O3···H21 | 2.6283 | C10···C8 | 3.592 (7) |
O3···H21 | 3.0298 | C10···H7 | 3.2295 |
O4···O2 | 2.693 (5) | C10···H7 | 2.9953 |
O4···O5 | 2.873 (5) | C10···H8 | 2.0158 |
O4···O6 | 3.586 (5) | C10···H8 | 3.1998 |
O4···O8 | 2.740 (5) | C10···H20 | 3.0361 |
O4···C11 | 2.694 (6) | C11···O4 | 3.582 (6) |
O4···C11 | 3.582 (6) | C11···O6 | 3.427 (6) |
O4···C12 | 3.587 (5) | C11···C13 | 2.474 (8) |
O4···C12 | 2.401 (5) | C11···H8 | 3.5504 |
O4···C14 | 2.435 (6) | C11···H9 | 3.5549 |
O4···C15 | 2.949 (6) | C11···H9 | 3.2250 |
O4···H10 | 2.7179 | C11···H10 | 2.0518 |
O4···H10 | 3.2255 | C11···H11 | 2.7118 |
O4···H10 | 3.3725 | C11···H11 | 3.2699 |
O4···H11 | 1.9844 | C11···H16 | 3.3067 |
O4···H11 | 2.7726 | C11···H16 | 2.8152 |
O4···H12 | 3.0036 | C11···H18 | 2.7068 |
O4···H12 | 3.2681 | C11···H21 | 3.2234 |
O4···H13 | 2.5189 | C12···O4 | 3.587 (5) |
O4···H17 | 2.7900 | C12···O8 | 3.372 (5) |
O4···H20 | 3.0319 | C12···C14 | 2.574 (7) |
O4···H21 | 1.8304 | C12···H9 | 3.1528 |
O5···O8 | 3.275 (5) | C12···H11 | 2.0697 |
O5···O9 | 3.397 (5) | C12···H11 | 3.4342 |
O5···O10 | 2.722 (6) | C12···H12 | 2.7660 |
O5···C12 | 2.979 (6) | C12···H16 | 3.0883 |
O5···C13 | 2.435 (7) | C12···H16 | 3.5328 |
O5···C15 | 2.392 (5) | C12···H16 | 3.1686 |
O5···C16 | 2.758 (7) | C12···H17 | 2.5272 |
O5···H1 | 3.0758 | C12···H20 | 2.6375 |
O5···H10 | 3.4332 | C12···H21 | 2.9251 |
O5···H11 | 3.2644 | C12···H21 | 3.2980 |
O5···H12 | 1.9824 | C13···O2 | 3.515 (6) |
O5···H13 | 2.6374 | C13···O2 | 3.361 (6) |
O5···H14 | 2.3242 | C13···C15 | 2.553 (8) |
O5···H15 | 3.1409 | C13···H10 | 2.0659 |
O5···H16 | 3.3183 | C13···H10 | 3.4060 |
O5···H20 | 3.3113 | C13···H11 | 3.5462 |
O5···H21 | 2.7520 | C13···H12 | 2.0664 |
O5···H22 | 3.3059 | C13···H13 | 2.6406 |
O5···H23 | 3.0679 | C13···H16 | 1.8817 |
O5···H24 | 1.7255 | C13···H16 | 3.2443 |
O5···H25 | 3.1623 | C13···H17 | 2.3935 |
O5···H27 | 3.2448 | C13···H18 | 2.9819 |
O6···O1 | 3.238 (5) | C13···H21 | 2.7098 |
O6···O2 | 3.374 (5) | C14···O2 | 3.193 (6) |
O6···O2 | 2.908 (5) | C14···C16 | 2.509 (8) |
O6···O7 | 2.913 (6) | C14···H10 | 2.8550 |
O6···C8 | 3.358 (6) | C14···H11 | 2.0637 |
O6···C11 | 3.427 (6) | C14···H13 | 2.0394 |
O6···C13 | 3.025 (7) | C14···H14 | 2.6128 |
O6···C14 | 2.442 (6) | C14···H15 | 2.7862 |
O6···C16 | 2.410 (6) | C14···H16 | 2.7011 |
O6···H5 | 3.1697 | C14···H16 | 3.4684 |
O6···H6 | 3.4545 | C14···H17 | 1.8767 |
O6···H6 | 3.2697 | C14···H18 | 2.4167 |
O6···H7 | 2.5763 | C14···H21 | 3.2232 |
O6···H9 | 3.3629 | C14···H24 | 2.6171 |
O6···H11 | 2.7057 | C15···O2 | 3.440 (6) |
O6···H12 | 2.6072 | C15···O2 | 3.591 (6) |
O6···H13 | 1.9559 | C15···H5 | 3.5180 |
O6···H14 | 3.2343 | C15···H11 | 2.7376 |
O6···H15 | 2.5808 | C15···H12 | 2.0663 |
O6···H16 | 3.2370 | C15···H14 | 2.0076 |
O6···H19 | 3.5122 | C15···H15 | 2.0077 |
O7···O11 | 2.716 (5) | C15···H16 | 2.7835 |
O7···N2 | 2.747 (5) | C15···H17 | 3.0711 |
O7···C4 | 3.239 (6) | C15···H18 | 1.8767 |
O7···C5 | 3.454 (6) | C15···H19 | 2.7876 |
O7···C6 | 3.590 (6) | C15···H24 | 3.3173 |
O7···C7 | 3.483 (6) | C16···O11 | 3.358 (7) |
O7···C15 | 2.397 (6) | C16···H4 | 3.1371 |
O7···H4 | 2.5316 | C16···H5 | 3.0101 |
O7···H5 | 1.9339 | C16···H12 | 2.7959 |
O7···H6 | 2.8021 | C16···H13 | 1.9801 |
O7···H13 | 2.4903 | C16···H17 | 3.5728 |
O7···H14 | 1.9922 | C16···H18 | 2.7909 |
O7···H15 | 1.9922 | C16···H19 | 1.8856 |
O7···H18 | 3.5073 | C16···H24 | 2.9770 |
O7···H26 | 3.1821 | C16···H26 | 3.5348 |
O7···H27 | 3.0297 | C16···H26 | 3.3415 |
O8···O3 | 2.723 (4) | C16···H27 | 3.3786 |
O8···O9 | 2.890 (5) | H1···O8 | 2.8130 |
O8···N1 | 3.392 (5) | H1···O9 | 3.2580 |
O8···N3 | 3.147 (6) | H2···O9 | 2.5615 |
O8···C1 | 3.235 (6) | H2···C3 | 3.0213 |
O8···C10 | 3.401 (6) | H2···C4 | 2.9542 |
O8···C12 | 3.372 (5) | H3···O9 | 3.3874 |
O8···C12 | 3.557 (5) | H3···C1 | 3.1804 |
O8···C13 | 3.576 (6) | H3···C2 | 2.8651 |
O8···H1 | 2.8130 | H3···C3 | 2.9826 |
O8···H1 | 3.5650 | H3···C4 | 3.3727 |
O8···H9 | 3.0759 | H4···O7 | 2.5316 |
O8···H10 | 2.9708 | H4···O9 | 3.1807 |
O8···H12 | 3.5969 | H4···O11 | 3.5765 |
O8···H16 | 3.3322 | H4···C7 | 3.5535 |
O8···H17 | 3.3565 | H4···C16 | 3.1371 |
O8···H17 | 2.7878 | H5···O6 | 3.1697 |
O8···H23 | 1.9267 | H5···O7 | 1.9339 |
O8···H24 | 3.5438 | H5···C8 | 3.2624 |
O8···H25 | 3.3268 | H5···C15 | 3.5180 |
O9···O10 | 2.737 (6) | H5···C16 | 3.0101 |
O9···O11 | 2.713 (6) | H6···O2 | 3.4404 |
O9···C1 | 3.595 (6) | H6···O6 | 3.2697 |
O9···C2 | 3.310 (6) | H6···O6 | 3.4545 |
O9···H1 | 3.2580 | H6···O7 | 2.8021 |
O9···H1 | 3.2161 | H7···O1 | 2.8090 |
O9···H2 | 2.5615 | H7···O6 | 2.5763 |
O9···H3 | 3.3874 | H7···N2 | 3.1508 |
O9···H4 | 3.1807 | H7···N3 | 3.5474 |
O9···H17 | 3.2114 | H7···C6 | 3.4933 |
O9···H20 | 3.4046 | H7···C9 | 3.3408 |
O9···H21 | 3.3285 | H7···C10 | 2.9953 |
O9···H24 | 3.2014 | H8···Cu1 | 3.0842 |
O9···H25 | 1.8241 | H8···O1 | 2.8222 |
O9···H26 | 3.0879 | H8···N3 | 3.2695 |
O9···H27 | 3.3957 | H8···N3 | 3.4306 |
O9···H27 | 3.0828 | H8···C6 | 3.5519 |
O10···O9 | 2.737 (6) | H8···C6 | 3.3383 |
O10···O11 | 2.729 (6) | H8···C7 | 3.0162 |
O10···O11 | 2.807 (6) | H8···C8 | 2.7858 |
O10···C14 | 3.546 (6) | H8···C9 | 2.9121 |
O10···C16 | 3.495 (7) | H8···C10 | 3.1998 |
O10···H1 | 3.5959 | H8···C11 | 3.5504 |
O10···H12 | 3.3336 | H9···Cu1 | 3.3697 |
O10···H14 | 2.8928 | H9···O1 | 3.2766 |
O10···H14 | 3.3050 | H9···O3 | 2.9659 |
O10···H15 | 3.2588 | H9···O6 | 3.3629 |
O10···H17 | 3.0740 | H9···C11 | 3.2250 |
O10···H22 | 3.0310 | H9···C12 | 3.1528 |
O10···H23 | 2.8483 | H10···O2 | 3.3802 |
O10···H26 | 2.8579 | H10···O4 | 2.7179 |
O10···H26 | 1.8613 | H10···O4 | 3.3725 |
O10···H27 | 1.8015 | H10···O8 | 2.9708 |
O10···H27 | 2.9174 | H10···C13 | 3.4060 |
O11···O7 | 2.716 (5) | H11···O2 | 3.3302 |
O11···O10 | 2.807 (6) | H11···O2 | 2.7960 |
O11···C16 | 3.358 (7) | H11···O4 | 2.7726 |
O11···H4 | 3.5765 | H11···C11 | 3.2699 |
O11···H14 | 3.5284 | H11···C12 | 3.4342 |
O11···H14 | 2.9618 | H11···C13 | 3.5462 |
O11···H15 | 2.8813 | H12···O2 | 2.5314 |
O11···H19 | 1.9401 | H12···O4 | 3.0036 |
O11···H22 | 1.8087 | H12···O8 | 3.5969 |
O11···H23 | 3.4850 | H13···O2 | 2.7036 |
O11···H24 | 2.9599 | H14···O10 | 3.3050 |
O11···H24 | 3.3927 | H14···O11 | 2.9618 |
O11···H25 | 3.5273 | H14···O11 | 3.5284 |
O11···H25 | 2.9401 | H15···O11 | 2.8813 |
O11···H25 | 3.3591 | H15···C4 | 3.5997 |
N1···N2 | 2.380 (6) | H16···O2 | 1.8765 |
N1···N3 | 2.864 (5) | H16···C11 | 2.8152 |
N1···C2 | 2.399 (6) | H16···C12 | 3.5328 |
N1···C3 | 2.771 (6) | H16···C12 | 3.1686 |
N1···C4 | 2.407 (6) | H16···C13 | 3.2443 |
N1···C6 | 3.000 (6) | H16···C14 | 3.4684 |
N1···H1 | 1.9822 | H17···O8 | 3.3565 |
N1···H2 | 3.2323 | H18···O1 | 2.6885 |
N1···H4 | 3.2408 | H18···O2 | 2.1117 |
N1···H5 | 3.1095 | H18···C7 | 3.4085 |
N1···H20 | 3.3443 | H18···C8 | 3.2313 |
N1···H23 | 3.4976 | H18···C11 | 2.7068 |
N2···O7 | 2.747 (5) | H19···O11 | 1.9401 |
N2···N3 | 2.355 (5) | H19···N2 | 3.2205 |
N2···C4 | 2.380 (6) | H20···Cu1 | 3.3502 |
N2···C7 | 2.379 (6) | H20···O3 | 1.8534 |
N2···C8 | 3.255 (6) | H20···O5 | 3.3113 |
N2···C9 | 3.600 (6) | H20···N1 | 3.3443 |
N2···C10 | 3.581 (6) | H20···C1 | 2.7946 |
N2···H4 | 2.5500 | H20···C2 | 3.5564 |
N2···H6 | 2.5413 | H20···C12 | 2.6375 |
N2···H7 | 3.1508 | H21···O3 | 3.0298 |
N2···H19 | 3.2205 | H21···C12 | 3.2980 |
N3···C5 | 2.996 (6) | H22···O10 | 3.0310 |
N3···C7 | 2.393 (6) | H23···O10 | 2.8483 |
N3···C8 | 2.787 (6) | H23···C1 | 3.2546 |
N3···C9 | 2.404 (6) | H23···C2 | 3.1610 |
N3···H5 | 3.0758 | H24···O8 | 3.5438 |
N3···H6 | 3.2217 | H24···O9 | 3.2014 |
N3···H7 | 3.5474 | H24···O11 | 3.3927 |
N3···H8 | 3.2368 | H25···O8 | 3.3268 |
N3···H8 | 3.2695 | H25···O9 | 1.8241 |
N3···H8 | 3.4306 | H25···O11 | 3.5273 |
N3···H9 | 1.9776 | H25···O11 | 3.3591 |
N3···H20 | 3.1085 | H26···O7 | 3.1821 |
C1···O8 | 3.235 (6) | H26···O10 | 1.8613 |
C1···C3 | 2.368 (7) | H26···C16 | 3.3415 |
C1···C4 | 2.723 (8) | H26···C16 | 3.5348 |
C1···C5 | 2.327 (7) | H27···O7 | 3.0297 |
C1···H2 | 2.0143 | H27···O9 | 3.3957 |
C1···H3 | 3.2102 | H27···O10 | 2.9174 |
C1···H3 | 3.1804 | H27···C16 | 3.3786 |
C1···H17 | 3.2744 | | |
| | | |
O1—Cu1—O3 | 84.5 (1) | H4—C4—C3 | 120.4348 |
O1—Cu1—O8 | 100.1 (1) | C7—C6—N2 | 117.1 (4) |
O1—Cu1—N1 | 157.7 (2) | C7—C6—N3 | 121.6 (4) |
O1—Cu1—N3 | 90.4 (1) | C8—C7—C6 | 119.8 (4) |
O3—Cu1—O8 | 87.0 (1) | C8—C7—H6 | 120.0782 |
O3—Cu1—N1 | 93.7 (1) | H6—C7—C6 | 120.0856 |
O3—Cu1—N3 | 174.8 (1) | C9—C8—C7 | 118.7 (4) |
O8—Cu1—N1 | 102.0 (1) | C9—C8—H7 | 120.6486 |
O8—Cu1—N3 | 92.9 (1) | H7—C8—C7 | 120.6357 |
N1—Cu1—N3 | 91.4 (2) | C10—C9—C8 | 118.4 (4) |
C11—O1—Cu1 | 114.1 (3) | C10—C9—H8 | 120.7934 |
C12—O3—Cu1 | 112.1 (3) | H8—C9—C8 | 120.7838 |
C13—O4—H16 | 109.4706 | H9—C10—N3 | 118.3881 |
C14—O5—H17 | 109.4708 | H9—C10—C9 | 118.3995 |
C15—O6—H18 | 109.4720 | C12—C11—O1 | 116.7 (4) |
C16—O7—H19 | 109.4672 | C12—C11—O2 | 120.8 (4) |
H20—O8—Cu1 | 114.7330 | C13—C12—O3 | 113.1 (4) |
H20—O8—H21 | 107.2020 | C13—C12—C11 | 107.8 (4) |
H21—O8—Cu1 | 91.7466 | C13—C12—H10 | 108.1967 |
H22—O9—H23 | 137.4809 | H10—C12—O3 | 108.1899 |
H24—O10—H25 | 108.6787 | H10—C12—C11 | 108.1980 |
H26—O11—H27 | 86.9886 | C14—C13—C12 | 114.0 (4) |
C1—N1—Cu1 | 118.4 (3) | C14—C13—O4 | 109.9 (4) |
C1—N1—C5 | 117.8 (4) | C14—C13—H11 | 108.5173 |
C5—N1—Cu1 | 122.6 (3) | H11—C13—C12 | 108.5054 |
C5—N2—C6 | 131.8 (4) | H11—C13—O4 | 108.5133 |
C5—N2—H5 | 114.1157 | C15—C14—C13 | 113.0 (4) |
C6—N2—H5 | 114.1174 | C15—C14—O5 | 107.4 (4) |
C6—N3—Cu1 | 125.2 (3) | C15—C14—H12 | 108.7439 |
C6—N3—C10 | 118.2 (4) | H12—C14—C13 | 108.7483 |
C10—N3—Cu1 | 116.5 (3) | H12—C14—O5 | 108.7468 |
C2—C1—N1 | 122.6 (5) | C16—C15—C14 | 113.8 (4) |
C2—C1—H1 | 118.7117 | C16—C15—O6 | 112.3 (4) |
H1—C1—N1 | 118.7003 | C16—C15—H13 | 106.5353 |
C3—C2—C1 | 118.8 (5) | H13—C15—C14 | 106.5292 |
C3—C2—H2 | 120.6150 | H13—C15—O6 | 106.5240 |
H2—C2—C1 | 120.6134 | H14—C16—C15 | 109.4594 |
C4—C3—C2 | 120.2 (5) | H14—C16—H15 | 108.0508 |
C4—C3—H3 | 119.8925 | H14—C16—O7 | 109.4700 |
H3—C3—C2 | 119.8751 | H15—C16—C15 | 109.4633 |
C5—C4—C3 | 119.1 (5) | H15—C16—O7 | 109.4644 |
C5—C4—H4 | 120.4492 | | |
| | | |
O3—Cu1—O1—C11 | −6.3 (3) | N1—C1—C2—C3 | −1.5 (7) |
O1—Cu1—O3—C12 | 10.7 (3) | C1—C2—C3—C4 | −0.9 (7) |
O1—Cu1—O8—H20 | 63.8 | C2—C3—C4—C5 | 0.3 (6) |
O1—Cu1—N1—C1 | 98.9 (4) | C3—C4—C5—N1 | 2.8 (7) |
O1—Cu1—N3—C6 | 136.6 (4) | C3—C4—C5—N2 | −178.0 (4) |
Cu1—O1—C11—O2 | −178.6 (4) | N2—C6—C7—C8 | 178.2 (5) |
Cu1—O3—C12—C11 | −12.8 (4) | C6—C7—C8—C9 | −0.9 (7) |
H16—O4—C13—C12 | −155.4 | C7—C8—C9—C10 | 2.4 (7) |
H17—O5—C14—C13 | 28.9 | C8—C9—C10—N3 | −2.3 (7) |
H18—O6—C15—C14 | −32.3 | O1—C11—C12—O3 | 8.2 (6) |
H19—O7—C16—C15 | 97.5 | O2—C11—C12—O3 | −172.7 (4) |
Cu1—N1—C1—C2 | −164.0 (4) | O3—C12—C13—O4 | −75.2 (5) |
Cu1—N1—C5—N2 | −16.3 (6) | C11—C12—C13—O4 | 48.2 (5) |
Cu1—N1—C5—C4 | 162.8 (4) | O4—C13—C14—O5 | 61.5 (5) |
C6—N2—C5—N1 | −8.7 (8) | C12—C13—C14—O5 | −58.9 (5) |
C6—N2—C5—C4 | 172.1 (4) | O5—C14—C15—O6 | 173.2 (4) |
C5—N2—C6—N3 | 14.4 (8) | C13—C14—C15—O6 | −65.2 (5) |
Cu1—N3—C6—N2 | 6.6 (7) | O6—C15—C16—O7 | 65.6 (5) |
Cu1—N3—C10—C9 | 176.3 (4) | C14—C15—C16—O7 | −167.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H16···O2i | 0.82 | 1.88 | 2.693 (6) | 173 |
O5—H17···O3 | 0.82 | 1.87 | 2.606 (5) | 148 |
O6—H18···O2ii | 0.82 | 2.11 | 2.908 (5) | 164 |
O7—H19···O11iii | 0.82 | 1.94 | 2.716 (6) | 158 |
O8—H20···O3iv | 0.89 | 1.85 | 2.723 (5) | 166 |
O8—H21···O4 | 0.92 | 1.83 | 2.740 (6) | 168 |
O9—H22···O11 | 0.90 | 1.81 | 2.713 (6) | 180 |
O9—H23···O8 | 0.96 | 1.93 | 2.890 (6) | 180 |
O10—H24···O5 | 1.00 | 1.73 | 2.722 (6) | 173 |
O10—H25···O9v | 0.91 | 1.82 | 2.737 (6) | 180 |
O11—H26···O10iii | 0.95 | 1.86 | 2.807 (6) | 179 |
O11—H27···O10 | 0.93 | 1.80 | 2.729 (7) | 178 |
N2—H5···O7vi | 0.86 | 1.93 | 2.747 (6) | 157 |
Symmetry codes: (i) −x, y−1/2, −z; (ii) −x, y+1/2, −z; (iii) −x, y−1/2, −z+1; (iv) x, y−1, z; (v) x, y+1, z; (vi) x+1, y, z. |