The title compound, [Cu(C6H12NO5)2], was prepared from copper(II) acetate and N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycine. The copper ion is coordinated by two N and four O atoms from two N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycine ligands, forming a distorted octahedral geometry. Extensive intermolecular hydrogen bonding is observed in the crystal structure.
Supporting information
CCDC reference: 294025
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.118
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.93
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O6 .. 2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. O2 .. 2.63 Ang.
PLAT726_ALERT_1_C H...A Calc 2.65(3), Rep 2.63000 Dev... 0.02 Ang.
H10 -O2 1.555 2.646
PLAT745_ALERT_1_C D-H Calc 0.77(4), Rep 0.77000 ...... Missing su
N1 -H1 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.87(4), Rep 0.87000 ...... Missing su
N2 -H2 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.84(4), Rep 0.84000 ...... Missing su
O3 -H3 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.85(3), Rep 0.85000 ...... Missing su
O4 -H4 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.85(3), Rep 0.85000 ...... Missing su
O4 -H4 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.842(12), Rep 0.84000 ...... Missing su
O5 -H5 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.842(12), Rep 0.84000 ...... Missing su
O5 -H5 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.84(3), Rep 0.84000 ...... Missing su
O8 -H8 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.85(2), Rep 0.85000 ...... Missing su
O9 -H9 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.84(3), Rep 0.84000 ...... Missing su
O10 -H10 1.555 1.555
PLAT745_ALERT_1_C D-H Calc 0.84(3), Rep 0.84000 ...... Missing su
O10 -H10 1.555 1.555
PLAT746_ALERT_1_C H...A Calc 2.24(4), Rep 2.24000 ...... Missing su
H1 -O5 1.555 3.566
PLAT746_ALERT_1_C H...A Calc 2.10(3), Rep 2.10000 ...... Missing su
H2 -O9 1.555 2.656
PLAT746_ALERT_1_C H...A Calc 1.80(4), Rep 1.80000 ...... Missing su
H3 -O2 1.555 4.576
PLAT746_ALERT_1_C H...A Calc 2.02(3), Rep 2.02000 ...... Missing su
H4 -O7 1.555 2.556
PLAT746_ALERT_1_C H...A Calc 2.44(3), Rep 2.44000 ...... Missing su
H4 -O6 1.555 2.556
PLAT746_ALERT_1_C H...A Calc 1.993(18), Rep 1.99000 ...... Missing su
H5 -O4 1.555 4.575
PLAT746_ALERT_1_C H...A Calc 2.65(4), Rep 2.65000 ...... Missing su
H5 -O6 1.555 3.566
PLAT746_ALERT_1_C H...A Calc 1.86(3), Rep 1.86000 ...... Missing su
H8 -O7 1.555 4.565
PLAT746_ALERT_1_C H...A Calc 1.92(2), Rep 1.92000 ...... Missing su
H9 -O10 1.555 4.565
PLAT746_ALERT_1_C H...A Calc 1.98(3), Rep 1.98000 ...... Missing su
H10 -O1 1.555 2.646
PLAT746_ALERT_1_C H...A Calc 2.65(3), Rep 2.63000 ...... Missing su
H10 -O2 1.555 2.646
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
30 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
26 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
Data collection: SMART (Bruker 1998); cell refinement: SAINT (Bruker 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 1999); software used to prepare material for publication: SHELXTL.
Bis{[2-hydroxy-
κO-1,1-bis(hydroxymethyl)ethylamino-
κN]acetato-
κO}copper(II)
top
Crystal data top
[Cu(C6H12NO5)2] | F(000) = 876 |
Mr = 419.87 | Dx = 1.757 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1891 reflections |
a = 14.343 (2) Å | θ = 2.8–26.2° |
b = 9.1271 (17) Å | µ = 1.44 mm−1 |
c = 12.2913 (18) Å | T = 293 K |
β = 99.460 (6)° | Block, colourless |
V = 1587.2 (5) Å3 | 0.32 × 0.22 × 0.16 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2798 independent reflections |
Radiation source: fine-focus sealed tube | 2127 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→17 |
Tmin = 0.680, Tmax = 0.791 | k = −10→10 |
7959 measured reflections | l = −14→14 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.0974P] where P = (Fo2 + 2Fc2)/3 |
2798 reflections | (Δ/σ)max = 0.001 |
258 parameters | Δρmax = 2.01 e Å−3 |
6 restraints | Δρmin = −0.51 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 >
2σ(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 | 0.25804 (3) | 0.50665 (4) | 0.66985 (3) | 0.01967 (17) | |
N1 | 0.1486 (2) | 0.5636 (3) | 0.5496 (2) | 0.0179 (6) | |
H1 | 0.116 (3) | 0.500 (4) | 0.560 (3) | 0.041 (14)* | |
N2 | 0.3624 (2) | 0.4330 (3) | 0.7910 (2) | 0.0171 (6) | |
H2 | 0.409 (3) | 0.495 (3) | 0.795 (3) | 0.027 (11)* | |
O1 | 0.33721 (16) | 0.5795 (2) | 0.56416 (16) | 0.0237 (5) | |
O2 | 0.33032 (17) | 0.6217 (3) | 0.38612 (18) | 0.0329 (6) | |
O3 | 0.2342 (2) | 0.7468 (2) | 0.7155 (2) | 0.0393 (7) | |
H3 | 0.266 (3) | 0.805 (4) | 0.760 (3) | 0.064 (14)* | |
O4 | 0.0069 (2) | 0.8188 (3) | 0.6885 (2) | 0.0385 (7) | |
H4 | −0.0451 (18) | 0.838 (5) | 0.647 (3) | 0.079 (17)* | |
O5 | −0.01588 (18) | 0.6782 (3) | 0.41121 (19) | 0.0338 (6) | |
H5 | −0.021 (3) | 0.684 (4) | 0.3421 (9) | 0.033 (11)* | |
O6 | 0.17497 (16) | 0.4378 (3) | 0.77036 (17) | 0.0274 (5) | |
O7 | 0.17250 (16) | 0.3797 (2) | 0.94399 (17) | 0.0296 (6) | |
O8 | 0.27372 (18) | 0.2671 (2) | 0.61013 (18) | 0.0299 (6) | |
H8 | 0.237 (2) | 0.212 (3) | 0.569 (2) | 0.034 (11)* | |
O9 | 0.49408 (19) | 0.1634 (2) | 0.65402 (19) | 0.0318 (6) | |
H9 | 0.499 (3) | 0.181 (5) | 0.5872 (14) | 0.073 (16)* | |
O10 | 0.51097 (18) | 0.2766 (3) | 0.93703 (19) | 0.0295 (6) | |
H10 | 0.5573 (17) | 0.220 (3) | 0.936 (3) | 0.040 (12)* | |
C1 | 0.2928 (2) | 0.5855 (3) | 0.4655 (3) | 0.0217 (7) | |
C2 | 0.1892 (2) | 0.5422 (4) | 0.4476 (3) | 0.0230 (7) | |
H2A | 0.1545 | 0.6010 | 0.3887 | 0.028* | |
H2B | 0.1830 | 0.4401 | 0.4255 | 0.028* | |
C3 | 0.1073 (2) | 0.7113 (3) | 0.5676 (2) | 0.0213 (7) | |
C4 | 0.1868 (3) | 0.8143 (3) | 0.6179 (3) | 0.0275 (8) | |
H4A | 0.2304 | 0.8303 | 0.5665 | 0.033* | |
H4B | 0.1611 | 0.9082 | 0.6351 | 0.033* | |
C5 | 0.0383 (2) | 0.6859 (4) | 0.6481 (3) | 0.0270 (8) | |
H5A | −0.0158 | 0.6314 | 0.6111 | 0.032* | |
H5B | 0.0690 | 0.6274 | 0.7095 | 0.032* | |
C6 | 0.0539 (3) | 0.7788 (3) | 0.4605 (3) | 0.0271 (8) | |
H6A | 0.0242 | 0.8699 | 0.4768 | 0.032* | |
H6B | 0.0977 | 0.7997 | 0.4102 | 0.032* | |
C7 | 0.2153 (2) | 0.4196 (3) | 0.8690 (3) | 0.0212 (7) | |
C8 | 0.3203 (2) | 0.4537 (4) | 0.8922 (3) | 0.0229 (7) | |
H8A | 0.3297 | 0.5540 | 0.9176 | 0.028* | |
H8B | 0.3513 | 0.3896 | 0.9500 | 0.028* | |
C9 | 0.3947 (2) | 0.2801 (3) | 0.7689 (2) | 0.0179 (7) | |
C10 | 0.3117 (2) | 0.1919 (3) | 0.7091 (2) | 0.0237 (7) | |
H10A | 0.3328 | 0.0949 | 0.6918 | 0.028* | |
H10B | 0.2637 | 0.1814 | 0.7556 | 0.028* | |
C11 | 0.4700 (2) | 0.3018 (3) | 0.6954 (3) | 0.0245 (8) | |
H11A | 0.4461 | 0.3663 | 0.6345 | 0.029* | |
H11B | 0.5258 | 0.3467 | 0.7377 | 0.029* | |
C12 | 0.4358 (3) | 0.1971 (3) | 0.8734 (2) | 0.0252 (8) | |
H12A | 0.3865 | 0.1802 | 0.9174 | 0.030* | |
H12B | 0.4589 | 0.1025 | 0.8536 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0200 (3) | 0.0205 (3) | 0.0174 (3) | 0.00075 (16) | −0.00020 (17) | 0.00415 (14) |
N1 | 0.0211 (16) | 0.0152 (14) | 0.0167 (13) | −0.0015 (12) | 0.0014 (11) | 0.0010 (10) |
N2 | 0.0176 (16) | 0.0149 (13) | 0.0180 (13) | 0.0005 (12) | 0.0006 (11) | −0.0001 (10) |
O1 | 0.0209 (13) | 0.0286 (12) | 0.0198 (11) | −0.0019 (10) | −0.0019 (10) | 0.0050 (9) |
O2 | 0.0271 (14) | 0.0481 (15) | 0.0242 (12) | 0.0027 (12) | 0.0058 (11) | 0.0139 (11) |
O3 | 0.0513 (18) | 0.0239 (13) | 0.0337 (15) | 0.0006 (13) | −0.0195 (13) | −0.0069 (11) |
O4 | 0.0379 (17) | 0.0445 (15) | 0.0315 (14) | 0.0208 (14) | 0.0012 (13) | −0.0074 (12) |
O5 | 0.0342 (15) | 0.0420 (14) | 0.0217 (13) | −0.0061 (12) | −0.0058 (12) | 0.0027 (11) |
O6 | 0.0225 (14) | 0.0342 (13) | 0.0237 (12) | −0.0002 (11) | −0.0015 (10) | 0.0079 (10) |
O7 | 0.0276 (14) | 0.0379 (13) | 0.0238 (12) | 0.0010 (11) | 0.0054 (11) | 0.0098 (10) |
O8 | 0.0393 (16) | 0.0210 (12) | 0.0235 (13) | −0.0045 (11) | −0.0126 (11) | −0.0036 (10) |
O9 | 0.0439 (17) | 0.0255 (12) | 0.0278 (14) | 0.0134 (12) | 0.0109 (12) | 0.0008 (10) |
O10 | 0.0254 (14) | 0.0317 (13) | 0.0277 (13) | 0.0033 (12) | −0.0060 (11) | −0.0020 (10) |
C1 | 0.0235 (19) | 0.0164 (15) | 0.0249 (17) | 0.0032 (14) | 0.0030 (15) | 0.0036 (13) |
C2 | 0.0228 (19) | 0.0257 (16) | 0.0201 (16) | −0.0009 (15) | 0.0026 (14) | −0.0026 (13) |
C3 | 0.0245 (19) | 0.0177 (15) | 0.0201 (16) | 0.0031 (14) | −0.0006 (14) | −0.0026 (12) |
C4 | 0.033 (2) | 0.0185 (16) | 0.0283 (18) | 0.0006 (15) | −0.0028 (16) | −0.0017 (14) |
C5 | 0.029 (2) | 0.0284 (18) | 0.0240 (17) | 0.0049 (16) | 0.0037 (15) | −0.0033 (14) |
C6 | 0.036 (2) | 0.0213 (16) | 0.0215 (17) | 0.0020 (16) | −0.0013 (16) | 0.0008 (13) |
C7 | 0.0232 (19) | 0.0149 (15) | 0.0245 (17) | 0.0039 (14) | 0.0013 (15) | 0.0010 (13) |
C8 | 0.026 (2) | 0.0223 (16) | 0.0204 (16) | 0.0021 (15) | 0.0023 (14) | −0.0028 (13) |
C9 | 0.0221 (18) | 0.0119 (14) | 0.0191 (16) | 0.0029 (13) | 0.0018 (14) | −0.0011 (12) |
C10 | 0.030 (2) | 0.0147 (15) | 0.0250 (17) | 0.0004 (14) | 0.0000 (15) | 0.0003 (13) |
C11 | 0.028 (2) | 0.0221 (17) | 0.0231 (17) | 0.0004 (15) | 0.0038 (15) | 0.0011 (13) |
C12 | 0.032 (2) | 0.0166 (15) | 0.0250 (17) | 0.0004 (15) | −0.0012 (15) | 0.0042 (13) |
Geometric parameters (Å, º) top
Cu1—O6 | 1.956 (2) | O10—C12 | 1.422 (4) |
Cu1—O1 | 1.976 (2) | O10—H10 | 0.84 (3) |
Cu1—N1 | 2.039 (3) | C1—C2 | 1.519 (5) |
Cu1—N2 | 2.044 (3) | C2—H2A | 0.9700 |
Cu1—O3 | 2.302 (2) | C2—H2B | 0.9700 |
Cu1—O8 | 2.329 (2) | C3—C5 | 1.528 (5) |
N1—C2 | 1.479 (4) | C3—C4 | 1.528 (4) |
N1—C3 | 1.503 (4) | C3—C6 | 1.538 (4) |
N1—H1 | 0.77 (4) | C4—H4A | 0.9700 |
N2—C8 | 1.482 (4) | C4—H4B | 0.9700 |
N2—C9 | 1.509 (4) | C5—H5A | 0.9700 |
N2—H2 | 0.87 (4) | C5—H5B | 0.9700 |
O1—C1 | 1.275 (4) | C6—H6A | 0.9700 |
O2—C1 | 1.234 (4) | C6—H6B | 0.9700 |
O3—C4 | 1.418 (4) | C7—C8 | 1.517 (5) |
O3—H3 | 0.84 (4) | C8—H8A | 0.9700 |
O4—C5 | 1.412 (4) | C8—H8B | 0.9700 |
O4—H4 | 0.85 (3) | C9—C10 | 1.521 (4) |
O5—C6 | 1.419 (4) | C9—C12 | 1.524 (4) |
O5—H5 | 0.842 (12) | C9—C11 | 1.531 (5) |
O6—C7 | 1.266 (4) | C10—H10A | 0.9700 |
O7—C7 | 1.243 (4) | C10—H10B | 0.9700 |
O8—C10 | 1.425 (4) | C11—H11A | 0.9700 |
O8—H8 | 0.84 (3) | C11—H11B | 0.9700 |
O9—C11 | 1.426 (4) | C12—H12A | 0.9700 |
O9—H9 | 0.85 (2) | C12—H12B | 0.9700 |
| | | |
O6—Cu1—O1 | 177.57 (8) | C4—C3—C6 | 109.5 (3) |
O6—Cu1—N1 | 93.64 (10) | O3—C4—C3 | 107.3 (3) |
O1—Cu1—N1 | 83.95 (10) | O3—C4—H4A | 110.3 |
O6—Cu1—N2 | 83.30 (10) | C3—C4—H4A | 110.3 |
O1—Cu1—N2 | 99.12 (10) | O3—C4—H4B | 110.3 |
N1—Cu1—N2 | 175.23 (10) | C3—C4—H4B | 110.3 |
O6—Cu1—O3 | 91.24 (11) | H4A—C4—H4B | 108.5 |
O1—Cu1—O3 | 87.95 (10) | O4—C5—C3 | 112.1 (3) |
N1—Cu1—O3 | 78.83 (9) | O4—C5—H5A | 109.2 |
N2—Cu1—O3 | 104.84 (9) | C3—C5—H5A | 109.2 |
O6—Cu1—O8 | 89.88 (10) | O4—C5—H5B | 109.2 |
O1—Cu1—O8 | 90.75 (9) | C3—C5—H5B | 109.2 |
N1—Cu1—O8 | 96.52 (9) | H5A—C5—H5B | 107.9 |
N2—Cu1—O8 | 79.85 (9) | O5—C6—C3 | 108.9 (3) |
O3—Cu1—O8 | 175.27 (7) | O5—C6—H6A | 109.9 |
C2—N1—C3 | 117.6 (2) | C3—C6—H6A | 109.9 |
C2—N1—Cu1 | 102.5 (2) | O5—C6—H6B | 109.9 |
C3—N1—Cu1 | 113.37 (18) | C3—C6—H6B | 109.9 |
C2—N1—H1 | 112 (3) | H6A—C6—H6B | 108.3 |
C3—N1—H1 | 112 (3) | O7—C7—O6 | 123.0 (3) |
Cu1—N1—H1 | 96 (3) | O7—C7—C8 | 121.1 (3) |
C8—N2—C9 | 116.6 (2) | O6—C7—C8 | 115.9 (3) |
C8—N2—Cu1 | 102.64 (19) | N2—C8—C7 | 110.2 (3) |
C9—N2—Cu1 | 112.49 (18) | N2—C8—H8A | 109.6 |
C8—N2—H2 | 107 (2) | C7—C8—H8A | 109.6 |
C9—N2—H2 | 111 (2) | N2—C8—H8B | 109.6 |
Cu1—N2—H2 | 107 (2) | C7—C8—H8B | 109.6 |
C1—O1—Cu1 | 112.9 (2) | H8A—C8—H8B | 108.1 |
C4—O3—Cu1 | 106.11 (18) | N2—C9—C10 | 109.7 (2) |
C4—O3—H3 | 115 (3) | N2—C9—C12 | 113.3 (2) |
Cu1—O3—H3 | 132 (3) | C10—C9—C12 | 107.9 (2) |
C5—O4—H4 | 106 (3) | N2—C9—C11 | 104.7 (2) |
C6—O5—H5 | 109 (2) | C10—C9—C11 | 110.8 (3) |
C7—O6—Cu1 | 114.7 (2) | C12—C9—C11 | 110.4 (3) |
C10—O8—Cu1 | 103.07 (16) | O8—C10—C9 | 108.5 (2) |
C10—O8—H8 | 110 (2) | O8—C10—H10A | 110.0 |
Cu1—O8—H8 | 133 (3) | C9—C10—H10A | 110.0 |
C11—O9—H9 | 104 (3) | O8—C10—H10B | 110.0 |
C12—O10—H10 | 102 (3) | C9—C10—H10B | 110.0 |
O2—C1—O1 | 123.3 (3) | H10A—C10—H10B | 108.4 |
O2—C1—C2 | 119.9 (3) | O9—C11—C9 | 109.4 (3) |
O1—C1—C2 | 116.8 (3) | O9—C11—H11A | 109.8 |
N1—C2—C1 | 110.8 (3) | C9—C11—H11A | 109.8 |
N1—C2—H2A | 109.5 | O9—C11—H11B | 109.8 |
C1—C2—H2A | 109.5 | C9—C11—H11B | 109.8 |
N1—C2—H2B | 109.5 | H11A—C11—H11B | 108.2 |
C1—C2—H2B | 109.5 | O10—C12—C9 | 111.3 (2) |
H2A—C2—H2B | 108.1 | O10—C12—H12A | 109.4 |
N1—C3—C5 | 105.8 (3) | C9—C12—H12A | 109.4 |
N1—C3—C4 | 109.0 (3) | O10—C12—H12B | 109.4 |
C5—C3—C4 | 110.5 (3) | C9—C12—H12B | 109.4 |
N1—C3—C6 | 112.7 (2) | H12A—C12—H12B | 108.0 |
C5—C3—C6 | 109.3 (3) | | |
| | | |
O6—Cu1—N1—C2 | −150.10 (19) | C2—N1—C3—C5 | 157.8 (3) |
O1—Cu1—N1—C2 | 30.26 (19) | Cu1—N1—C3—C5 | −82.7 (3) |
O3—Cu1—N1—C2 | 119.4 (2) | C2—N1—C3—C4 | −83.3 (3) |
O8—Cu1—N1—C2 | −59.8 (2) | Cu1—N1—C3—C4 | 36.2 (3) |
O6—Cu1—N1—C3 | 82.1 (2) | C2—N1—C3—C6 | 38.5 (4) |
O1—Cu1—N1—C3 | −97.5 (2) | Cu1—N1—C3—C6 | 158.0 (2) |
O3—Cu1—N1—C3 | −8.4 (2) | Cu1—O3—C4—C3 | 46.1 (3) |
O8—Cu1—N1—C3 | 172.4 (2) | N1—C3—C4—O3 | −55.8 (3) |
O6—Cu1—N2—C8 | −30.05 (18) | C5—C3—C4—O3 | 60.0 (3) |
O1—Cu1—N2—C8 | 149.74 (19) | C6—C3—C4—O3 | −179.5 (3) |
O3—Cu1—N2—C8 | 59.5 (2) | N1—C3—C5—O4 | 169.1 (3) |
O8—Cu1—N2—C8 | −121.1 (2) | C4—C3—C5—O4 | 51.3 (3) |
O6—Cu1—N2—C9 | 96.1 (2) | C6—C3—C5—O4 | −69.3 (3) |
O1—Cu1—N2—C9 | −84.1 (2) | N1—C3—C6—O5 | 55.0 (4) |
O3—Cu1—N2—C9 | −174.4 (2) | C5—C3—C6—O5 | −62.3 (3) |
O8—Cu1—N2—C9 | 5.0 (2) | C4—C3—C6—O5 | 176.5 (3) |
N1—Cu1—O1—C1 | −19.4 (2) | Cu1—O6—C7—O7 | 178.2 (2) |
N2—Cu1—O1—C1 | 157.0 (2) | Cu1—O6—C7—C8 | −0.1 (3) |
O3—Cu1—O1—C1 | −98.3 (2) | C9—N2—C8—C7 | −86.3 (3) |
O8—Cu1—O1—C1 | 77.1 (2) | Cu1—N2—C8—C7 | 37.2 (3) |
O6—Cu1—O3—C4 | −115.3 (2) | O7—C7—C8—N2 | 154.7 (3) |
O1—Cu1—O3—C4 | 62.4 (2) | O6—C7—C8—N2 | −27.0 (4) |
N1—Cu1—O3—C4 | −21.9 (2) | C8—N2—C9—C10 | 85.0 (3) |
N2—Cu1—O3—C4 | 161.3 (2) | Cu1—N2—C9—C10 | −33.2 (3) |
N1—Cu1—O6—C7 | −165.5 (2) | C8—N2—C9—C12 | −35.7 (4) |
N2—Cu1—O6—C7 | 18.2 (2) | Cu1—N2—C9—C12 | −153.9 (2) |
O3—Cu1—O6—C7 | −86.6 (2) | C8—N2—C9—C11 | −156.0 (3) |
O8—Cu1—O6—C7 | 98.0 (2) | Cu1—N2—C9—C11 | 85.8 (2) |
O6—Cu1—O8—C10 | −58.7 (2) | Cu1—O8—C10—C9 | −48.5 (3) |
O1—Cu1—O8—C10 | 123.7 (2) | N2—C9—C10—O8 | 57.1 (3) |
N1—Cu1—O8—C10 | −152.3 (2) | C12—C9—C10—O8 | −179.0 (3) |
N2—Cu1—O8—C10 | 24.5 (2) | C11—C9—C10—O8 | −58.0 (3) |
Cu1—O1—C1—O2 | −176.6 (2) | N2—C9—C11—O9 | −170.2 (2) |
Cu1—O1—C1—C2 | 2.0 (3) | C10—C9—C11—O9 | −52.0 (3) |
C3—N1—C2—C1 | 88.6 (3) | C12—C9—C11—O9 | 67.5 (3) |
Cu1—N1—C2—C1 | −36.5 (3) | N2—C9—C12—O10 | −55.3 (4) |
O2—C1—C2—N1 | −156.1 (3) | C10—C9—C12—O10 | −177.0 (3) |
O1—C1—C2—N1 | 25.2 (4) | C11—C9—C12—O10 | 61.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5i | 0.77 | 2.24 | 3.004 (3) | 178 |
N2—H2···O9ii | 0.87 | 2.10 | 2.942 (4) | 163 |
O3—H3···O2iii | 0.84 | 1.80 | 2.606 (3) | 161 |
O4—H4···O7iv | 0.85 | 2.02 | 2.865 (4) | 177 |
O4—H4···O6iv | 0.85 | 2.44 | 2.945 (2) | 119 |
O5—H5···O4v | 0.84 | 1.99 | 2.809 (3) | 163 |
O5—H5···O6i | 0.84 | 2.65 | 3.104 (4) | 115 |
O8—H8···O7vi | 0.84 | 1.86 | 2.664 (3) | 162 |
O9—H9···O10vi | 0.85 | 1.92 | 2.772 (2) | 179 |
O10—H10···O1vii | 0.84 | 1.98 | 2.826 (3) | 177 |
O10—H10···O2vii | 0.84 | 2.63 | 3.206 (4) | 125 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2; (iii) x, −y+3/2, z+1/2; (iv) −x, y+1/2, −z+3/2; (v) x, −y+3/2, z−1/2; (vi) x, −y+1/2, z−1/2; (vii) −x+1, y−1/2, −z+3/2. |