Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038602/ww6396sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038602/ww6396Isup2.hkl |
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.
[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 |
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 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 |
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. |
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* |
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) |
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) |
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. |
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