The structure of the title compound, {μ-2-[N,N-bis(carboxylatomethyl)aminomethyl]-6-[N-(carboxylatomethyl)-N-(carboxymethyl)aminomethyl]-6-methylphenolato}dicopper(II) tetrahydrate, [Cu2(C17H17N2O9)(H2O)2]·4H2O, which has been published previously [Holz, Brink, Gobena & O'Connor (1994). Inorg. Chem. 33, 6086–6092], has been redetermined. The H atom missing in the earlier study is shown to be associated with a carboxyl group.
Supporting information
CCDC reference: 242047
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.004 Å
- R factor = 0.031
- wR factor = 0.082
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.34
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.08 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu2 - O1 .. 5.83 su
PLAT354_ALERT_3_C Short O-H Bond (0.82A) O14 - H14D ... 0.67 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D H5 .. H15A .. 2.11 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3
O6 -CU1 -N1 -C9 -78.40 0.70 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 7
O6 -CU1 -N1 -C11 40.70 0.80 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11
O6 -CU1 -N1 -C8 158.50 0.70 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 37
O11 -CU2 -N2 -C16 48.40 0.60 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 41
O11 -CU2 -N2 -C14 -72.90 0.60 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 45
O11 -CU2 -N2 -C13 165.70 0.50 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
6 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 2000); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.
Crystal data top
[Cu2(C17H17N2O9)(H2O)2]·4H2O | F(000) = 1296 |
Mr = 629.51 | Dx = 1.741 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5375 reflections |
a = 15.0895 (18) Å | θ = 2.3–26.9° |
b = 10.8217 (13) Å | µ = 1.85 mm−1 |
c = 15.2048 (18) Å | T = 183 K |
β = 104.705 (2)° | Plate, dark green |
V = 2401.5 (5) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 4221 independent reflections |
Radiation source: fine-focus sealed tube | 3623 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→17 |
Tmin = 0.509, Tmax = 0.688 | k = −11→12 |
9615 measured reflections | l = −18→16 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3 |
4221 reflections | (Δ/σ)max < 0.001 |
378 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.30 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 | −0.03791 (2) | 0.05828 (3) | 0.16776 (2) | 0.01934 (11) | |
N1 | −0.00732 (15) | −0.12570 (19) | 0.16955 (13) | 0.0175 (5) | |
O1 | 0.05425 (12) | 0.10003 (16) | 0.27464 (11) | 0.0202 (4) | |
O2 | −0.11336 (13) | 0.02084 (16) | 0.04667 (11) | 0.0230 (4) | |
O3 | −0.11788 (15) | −0.10314 (18) | −0.07040 (12) | 0.0335 (5) | |
O4 | −0.13778 (13) | −0.01431 (18) | 0.24736 (13) | 0.0281 (5) | |
O5 | −0.19054 (15) | −0.1904 (2) | 0.28412 (14) | 0.0336 (5) | |
O6 | −0.08006 (16) | 0.22980 (19) | 0.15187 (16) | 0.0300 (5) | |
Cu2 | 0.13248 (2) | 0.27618 (3) | 0.30574 (2) | 0.01999 (11) | |
N2 | 0.12514 (15) | 0.27939 (19) | 0.43529 (13) | 0.0186 (5) | |
O7 | 0.25230 (12) | 0.19809 (17) | 0.35440 (11) | 0.0234 (4) | |
O8 | 0.35682 (12) | 0.16534 (17) | 0.48399 (12) | 0.0241 (4) | |
O9 | 0.01858 (12) | 0.37597 (16) | 0.28550 (11) | 0.0225 (4) | |
O10 | −0.05018 (15) | 0.5041 (2) | 0.36146 (13) | 0.0400 (6) | |
O11 | 0.14780 (15) | 0.3000 (2) | 0.18352 (14) | 0.0263 (5) | |
C1 | 0.1810 (2) | −0.2523 (3) | 0.5554 (2) | 0.0346 (8) | |
H1A | 0.1354 | −0.3182 | 0.5501 | 0.052* | |
H1B | 0.1907 | −0.2124 | 0.6149 | 0.052* | |
H1C | 0.2389 | −0.2875 | 0.5491 | 0.052* | |
C2 | 0.14693 (18) | −0.1576 (3) | 0.48117 (17) | 0.0234 (6) | |
C3 | 0.13360 (18) | −0.1905 (3) | 0.39069 (18) | 0.0246 (6) | |
H3 | 0.1459 | −0.2731 | 0.3762 | 0.030* | |
C4 | 0.10284 (18) | −0.1068 (2) | 0.32049 (17) | 0.0209 (6) | |
C5 | 0.08298 (18) | 0.0146 (2) | 0.34075 (17) | 0.0194 (6) | |
C6 | 0.09495 (18) | 0.0498 (2) | 0.43174 (17) | 0.0203 (6) | |
C7 | 0.12721 (19) | −0.0366 (3) | 0.50001 (18) | 0.0233 (6) | |
H7 | 0.1361 | −0.0121 | 0.5616 | 0.028* | |
C8 | 0.09036 (18) | −0.1449 (2) | 0.22319 (17) | 0.0214 (6) | |
H8A | 0.1069 | −0.2331 | 0.2207 | 0.026* | |
H8B | 0.1318 | −0.0957 | 0.1957 | 0.026* | |
C9 | −0.07092 (18) | −0.2007 (2) | 0.20733 (18) | 0.0215 (6) | |
H9A | −0.0344 | −0.2563 | 0.2545 | 0.026* | |
H9B | −0.1079 | −0.2532 | 0.1582 | 0.026* | |
C10 | −0.13503 (19) | −0.1273 (3) | 0.24841 (17) | 0.0227 (6) | |
C11 | −0.01750 (19) | −0.1576 (2) | 0.07196 (16) | 0.0221 (6) | |
H11A | −0.0358 | −0.2453 | 0.0615 | 0.027* | |
H11B | 0.0420 | −0.1466 | 0.0567 | 0.027* | |
C12 | −0.08910 (19) | −0.0759 (2) | 0.01112 (18) | 0.0226 (6) | |
C13 | 0.06582 (19) | 0.1767 (3) | 0.45274 (17) | 0.0228 (6) | |
H13A | 0.0025 | 0.1913 | 0.4159 | 0.027* | |
H13B | 0.0647 | 0.1794 | 0.5175 | 0.027* | |
C14 | 0.21993 (18) | 0.2677 (2) | 0.49170 (17) | 0.0217 (6) | |
H14A | 0.2200 | 0.2197 | 0.5471 | 0.026* | |
H14B | 0.2448 | 0.3509 | 0.5108 | 0.026* | |
C15 | 0.28039 (19) | 0.2042 (2) | 0.44023 (18) | 0.0217 (6) | |
C16 | 0.08124 (19) | 0.3986 (3) | 0.44491 (17) | 0.0245 (6) | |
H16A | 0.1282 | 0.4646 | 0.4586 | 0.029* | |
H16B | 0.0518 | 0.3940 | 0.4961 | 0.029* | |
C17 | 0.0095 (2) | 0.4296 (2) | 0.35743 (18) | 0.0242 (6) | |
O12 | 0.0809 (2) | 0.5244 (2) | 0.14152 (18) | 0.0423 (6) | |
O13 | 0.2062 (2) | 0.5036 (2) | 0.3297 (2) | 0.0422 (6) | |
O14 | 0.38904 (19) | 0.9524 (2) | 0.5929 (2) | 0.0414 (6) | |
H13C | 0.253 (3) | 0.525 (3) | 0.347 (2) | 0.046 (14)* | |
H14C | 0.363 (3) | 0.964 (4) | 0.631 (3) | 0.055 (14)* | |
H11D | 0.126 (2) | 0.370 (3) | 0.162 (2) | 0.040 (10)* | |
H6B | −0.055 (2) | 0.282 (3) | 0.188 (2) | 0.038 (10)* | |
H12B | 0.104 (3) | 0.565 (3) | 0.101 (3) | 0.062 (13)* | |
H6A | −0.090 (3) | 0.250 (4) | 0.102 (3) | 0.056 (13)* | |
H13D | 0.195 (3) | 0.540 (3) | 0.286 (2) | 0.038 (12)* | |
H11C | 0.134 (3) | 0.248 (4) | 0.151 (2) | 0.053 (13)* | |
H14D | 0.372 (4) | 0.985 (5) | 0.555 (3) | 0.10 (2)* | |
H12A | 0.027 (3) | 0.523 (4) | 0.118 (2) | 0.054 (14)* | |
O15 | 0.30668 (17) | 0.9176 (2) | 0.74364 (15) | 0.0328 (5) | |
H15B | 0.256 (3) | 0.963 (3) | 0.750 (2) | 0.042 (10)* | |
H15A | 0.347 (2) | 0.953 (3) | 0.775 (2) | 0.024 (9)* | |
H5 | −0.188 (3) | −0.264 (4) | 0.273 (3) | 0.080 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0226 (2) | 0.01678 (19) | 0.01651 (18) | 0.00049 (13) | 0.00103 (14) | −0.00156 (13) |
N1 | 0.0216 (12) | 0.0169 (11) | 0.0138 (10) | 0.0022 (9) | 0.0043 (9) | −0.0009 (9) |
O1 | 0.0251 (10) | 0.0168 (9) | 0.0158 (9) | −0.0019 (8) | 0.0002 (8) | −0.0003 (7) |
O2 | 0.0270 (11) | 0.0199 (10) | 0.0186 (9) | 0.0039 (8) | −0.0006 (8) | −0.0033 (8) |
O3 | 0.0484 (14) | 0.0278 (11) | 0.0186 (10) | 0.0067 (10) | −0.0020 (9) | −0.0058 (8) |
O4 | 0.0322 (12) | 0.0223 (11) | 0.0334 (11) | 0.0008 (9) | 0.0152 (9) | −0.0024 (9) |
O5 | 0.0383 (13) | 0.0300 (13) | 0.0389 (13) | −0.0018 (10) | 0.0214 (10) | −0.0005 (10) |
O6 | 0.0409 (14) | 0.0189 (11) | 0.0224 (12) | 0.0039 (9) | −0.0066 (10) | −0.0027 (10) |
Cu2 | 0.0215 (2) | 0.0221 (2) | 0.01582 (18) | 0.00135 (13) | 0.00368 (14) | −0.00167 (13) |
N2 | 0.0206 (12) | 0.0195 (12) | 0.0143 (11) | −0.0005 (9) | 0.0021 (9) | −0.0033 (9) |
O7 | 0.0220 (10) | 0.0278 (11) | 0.0197 (10) | 0.0032 (8) | 0.0042 (8) | −0.0006 (8) |
O8 | 0.0210 (10) | 0.0259 (11) | 0.0233 (10) | 0.0025 (8) | 0.0017 (8) | 0.0013 (8) |
O9 | 0.0245 (10) | 0.0232 (10) | 0.0179 (9) | 0.0025 (8) | 0.0020 (8) | −0.0022 (8) |
O10 | 0.0417 (14) | 0.0452 (14) | 0.0298 (12) | 0.0234 (11) | 0.0027 (10) | −0.0060 (10) |
O11 | 0.0362 (13) | 0.0221 (12) | 0.0199 (11) | 0.0003 (10) | 0.0058 (9) | −0.0021 (10) |
C1 | 0.0397 (19) | 0.0320 (17) | 0.0265 (16) | 0.0020 (14) | −0.0019 (14) | 0.0067 (13) |
C2 | 0.0208 (15) | 0.0263 (15) | 0.0198 (14) | −0.0003 (12) | −0.0010 (11) | 0.0036 (12) |
C3 | 0.0206 (15) | 0.0208 (14) | 0.0298 (15) | 0.0020 (12) | 0.0017 (12) | −0.0006 (12) |
C4 | 0.0176 (14) | 0.0227 (15) | 0.0208 (13) | −0.0024 (11) | 0.0019 (11) | 0.0012 (11) |
C5 | 0.0154 (14) | 0.0215 (14) | 0.0193 (14) | −0.0009 (11) | 0.0008 (11) | 0.0019 (11) |
C6 | 0.0162 (14) | 0.0238 (15) | 0.0207 (14) | −0.0028 (11) | 0.0043 (11) | −0.0020 (11) |
C7 | 0.0215 (15) | 0.0319 (16) | 0.0152 (13) | −0.0055 (12) | 0.0020 (11) | −0.0007 (11) |
C8 | 0.0207 (15) | 0.0212 (15) | 0.0211 (14) | 0.0048 (11) | 0.0030 (11) | −0.0002 (11) |
C9 | 0.0220 (15) | 0.0183 (14) | 0.0230 (14) | −0.0020 (11) | 0.0037 (12) | −0.0022 (11) |
C10 | 0.0228 (15) | 0.0283 (17) | 0.0170 (13) | −0.0020 (12) | 0.0053 (11) | −0.0003 (12) |
C11 | 0.0291 (16) | 0.0208 (14) | 0.0159 (13) | 0.0027 (12) | 0.0048 (11) | −0.0024 (11) |
C12 | 0.0267 (16) | 0.0203 (15) | 0.0208 (14) | −0.0010 (12) | 0.0062 (12) | −0.0006 (11) |
C13 | 0.0207 (15) | 0.0303 (16) | 0.0181 (13) | −0.0004 (12) | 0.0061 (11) | −0.0009 (12) |
C14 | 0.0223 (15) | 0.0249 (15) | 0.0169 (13) | −0.0008 (11) | 0.0031 (11) | −0.0023 (11) |
C15 | 0.0231 (15) | 0.0182 (14) | 0.0234 (15) | −0.0041 (11) | 0.0050 (12) | 0.0019 (11) |
C16 | 0.0248 (15) | 0.0282 (16) | 0.0188 (14) | 0.0023 (12) | 0.0022 (12) | −0.0063 (12) |
C17 | 0.0268 (16) | 0.0229 (15) | 0.0214 (14) | 0.0014 (12) | 0.0035 (12) | −0.0015 (12) |
O12 | 0.0432 (17) | 0.0365 (14) | 0.0514 (15) | 0.0011 (12) | 0.0196 (14) | 0.0149 (12) |
O13 | 0.0407 (17) | 0.0409 (15) | 0.0402 (16) | −0.0039 (13) | 0.0014 (13) | −0.0062 (13) |
O14 | 0.0490 (16) | 0.0362 (14) | 0.0419 (16) | 0.0101 (11) | 0.0167 (14) | 0.0126 (12) |
O15 | 0.0256 (13) | 0.0289 (12) | 0.0419 (13) | 0.0007 (10) | 0.0045 (11) | −0.0116 (10) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.9056 (17) | C2—C3 | 1.385 (4) |
Cu1—O2 | 1.9457 (17) | C2—C7 | 1.389 (4) |
Cu1—O6 | 1.957 (2) | C3—C4 | 1.387 (4) |
Cu1—N1 | 2.042 (2) | C3—H3 | 0.9500 |
Cu1—O4 | 2.298 (2) | C4—C5 | 1.399 (4) |
N1—C9 | 1.480 (3) | C4—C8 | 1.501 (3) |
N1—C11 | 1.493 (3) | C5—C6 | 1.402 (4) |
N1—C8 | 1.507 (3) | C6—C7 | 1.390 (4) |
O1—C5 | 1.353 (3) | C6—C13 | 1.501 (4) |
O1—Cu2 | 2.2288 (17) | C7—H7 | 0.9500 |
O2—C12 | 1.273 (3) | C8—H8A | 0.9900 |
O3—C12 | 1.240 (3) | C8—H8B | 0.9900 |
O4—C10 | 1.224 (3) | C9—C10 | 1.504 (4) |
O5—C10 | 1.301 (3) | C9—H9A | 0.9900 |
O5—H5 | 0.82 (4) | C9—H9B | 0.9900 |
O6—H6B | 0.81 (3) | C11—C12 | 1.516 (4) |
O6—H6A | 0.76 (4) | C11—H11A | 0.9900 |
Cu2—O11 | 1.947 (2) | C11—H11B | 0.9900 |
Cu2—O7 | 1.9624 (18) | C13—H13A | 0.9900 |
Cu2—O9 | 1.9866 (18) | C13—H13B | 0.9900 |
Cu2—N2 | 2.001 (2) | C14—C15 | 1.510 (4) |
N2—C16 | 1.475 (3) | C14—H14A | 0.9900 |
N2—C14 | 1.475 (3) | C14—H14B | 0.9900 |
N2—C13 | 1.492 (3) | C16—C17 | 1.523 (4) |
O7—C15 | 1.267 (3) | C16—H16A | 0.9900 |
O8—C15 | 1.249 (3) | C16—H16B | 0.9900 |
O9—C17 | 1.276 (3) | O12—H12B | 0.90 (4) |
O10—C17 | 1.223 (3) | O12—H12A | 0.80 (4) |
O11—H11D | 0.86 (3) | O13—H13C | 0.73 (4) |
O11—H11C | 0.75 (4) | O13—H13D | 0.76 (3) |
C1—C2 | 1.514 (4) | O14—H14C | 0.79 (4) |
C1—H1A | 0.9800 | O14—H14D | 0.67 (5) |
C1—H1B | 0.9800 | O15—H15B | 0.94 (4) |
C1—H1C | 0.9800 | O15—H15A | 0.77 (3) |
| | | |
Cu1···Cu2 | 3.7194 (6) | | |
| | | |
O1—Cu1—O2 | 168.91 (8) | O1—C5—C4 | 121.6 (2) |
O1—Cu1—O6 | 91.40 (9) | O1—C5—C6 | 119.0 (2) |
O2—Cu1—O6 | 89.25 (9) | C4—C5—C6 | 119.4 (2) |
O1—Cu1—N1 | 96.10 (8) | C7—C6—C5 | 119.1 (2) |
O2—Cu1—N1 | 83.43 (8) | C7—C6—C13 | 121.5 (2) |
O6—Cu1—N1 | 172.50 (9) | C5—C6—C13 | 119.2 (2) |
O1—Cu1—O4 | 93.79 (7) | C2—C7—C6 | 122.2 (2) |
O2—Cu1—O4 | 97.05 (8) | C2—C7—H7 | 118.9 |
O6—Cu1—O4 | 98.82 (9) | C6—C7—H7 | 118.9 |
N1—Cu1—O4 | 80.56 (8) | C4—C8—N1 | 110.9 (2) |
C9—N1—C11 | 110.2 (2) | C4—C8—H8A | 109.5 |
C9—N1—C8 | 110.85 (19) | N1—C8—H8A | 109.5 |
C11—N1—C8 | 110.2 (2) | C4—C8—H8B | 109.5 |
C9—N1—Cu1 | 111.91 (16) | N1—C8—H8B | 109.5 |
C11—N1—Cu1 | 104.26 (15) | H8A—C8—H8B | 108.0 |
C8—N1—Cu1 | 109.16 (15) | N1—C9—C10 | 114.9 (2) |
C5—O1—Cu1 | 119.89 (15) | N1—C9—H9A | 108.6 |
C5—O1—Cu2 | 111.96 (14) | C10—C9—H9A | 108.6 |
Cu1—O1—Cu2 | 128.05 (8) | N1—C9—H9B | 108.6 |
C12—O2—Cu1 | 114.25 (16) | C10—C9—H9B | 108.6 |
C10—O4—Cu1 | 108.90 (17) | H9A—C9—H9B | 107.5 |
C10—O5—H5 | 111 (3) | O4—C10—O5 | 120.4 (3) |
Cu1—O6—H6B | 120 (2) | O4—C10—C9 | 123.0 (2) |
Cu1—O6—H6A | 112 (3) | O5—C10—C9 | 116.5 (2) |
H6B—O6—H6A | 114 (4) | N1—C11—C12 | 110.4 (2) |
O11—Cu2—O7 | 95.49 (8) | N1—C11—H11A | 109.6 |
O11—Cu2—O9 | 95.05 (8) | C12—C11—H11A | 109.6 |
O7—Cu2—O9 | 166.05 (7) | N1—C11—H11B | 109.6 |
O11—Cu2—N2 | 170.69 (9) | C12—C11—H11B | 109.6 |
O7—Cu2—N2 | 84.96 (8) | H11A—C11—H11B | 108.1 |
O9—Cu2—N2 | 83.17 (8) | O3—C12—O2 | 123.7 (2) |
O11—Cu2—O1 | 95.47 (8) | O3—C12—C11 | 119.0 (2) |
O7—Cu2—O1 | 95.70 (7) | O2—C12—C11 | 117.2 (2) |
O9—Cu2—O1 | 92.36 (7) | N2—C13—C6 | 115.0 (2) |
N2—Cu2—O1 | 93.73 (7) | N2—C13—H13A | 108.5 |
C16—N2—C14 | 114.3 (2) | C6—C13—H13A | 108.5 |
C16—N2—C13 | 109.2 (2) | N2—C13—H13B | 108.5 |
C14—N2—C13 | 111.7 (2) | C6—C13—H13B | 108.5 |
C16—N2—Cu2 | 104.55 (15) | H13A—C13—H13B | 107.5 |
C14—N2—Cu2 | 106.45 (16) | N2—C14—C15 | 111.2 (2) |
C13—N2—Cu2 | 110.35 (15) | N2—C14—H14A | 109.4 |
C15—O7—Cu2 | 113.64 (17) | C15—C14—H14A | 109.4 |
C17—O9—Cu2 | 113.02 (16) | N2—C14—H14B | 109.4 |
Cu2—O11—H11D | 111 (2) | C15—C14—H14B | 109.4 |
Cu2—O11—H11C | 117 (3) | H14A—C14—H14B | 108.0 |
H11D—O11—H11C | 114 (3) | O8—C15—O7 | 123.6 (3) |
C2—C1—H1A | 109.5 | O8—C15—C14 | 118.4 (2) |
C2—C1—H1B | 109.5 | O7—C15—C14 | 118.0 (2) |
H1A—C1—H1B | 109.5 | N2—C16—C17 | 110.1 (2) |
C2—C1—H1C | 109.5 | N2—C16—H16A | 109.6 |
H1A—C1—H1C | 109.5 | C17—C16—H16A | 109.6 |
H1B—C1—H1C | 109.5 | N2—C16—H16B | 109.6 |
C3—C2—C7 | 117.5 (2) | C17—C16—H16B | 109.6 |
C3—C2—C1 | 120.2 (3) | H16A—C16—H16B | 108.2 |
C7—C2—C1 | 122.3 (2) | O10—C17—O9 | 125.7 (2) |
C2—C3—C4 | 122.2 (3) | O10—C17—C16 | 118.1 (2) |
C2—C3—H3 | 118.9 | O9—C17—C16 | 116.2 (2) |
C4—C3—H3 | 118.9 | H12B—O12—H12A | 104 (4) |
C3—C4—C5 | 119.5 (2) | H13C—O13—H13D | 98 (4) |
C3—C4—C8 | 120.9 (2) | H14C—O14—H14D | 114 (5) |
C5—C4—C8 | 119.7 (2) | H15B—O15—H15A | 102 (3) |
| | | |
O1—Cu1—N1—C9 | 100.25 (16) | C1—C2—C3—C4 | −179.8 (3) |
O2—Cu1—N1—C9 | −90.90 (16) | C2—C3—C4—C5 | −1.1 (4) |
O6—Cu1—N1—C9 | −78.4 (7) | C2—C3—C4—C8 | 179.1 (3) |
O4—Cu1—N1—C9 | 7.40 (15) | Cu1—O1—C5—C4 | 45.2 (3) |
O1—Cu1—N1—C11 | −140.62 (16) | Cu2—O1—C5—C4 | −131.4 (2) |
O2—Cu1—N1—C11 | 28.23 (16) | Cu1—O1—C5—C6 | −136.3 (2) |
O6—Cu1—N1—C11 | 40.7 (8) | Cu2—O1—C5—C6 | 47.2 (3) |
O4—Cu1—N1—C11 | 126.54 (16) | C3—C4—C5—O1 | 178.9 (2) |
O1—Cu1—N1—C8 | −22.84 (17) | C8—C4—C5—O1 | −1.3 (4) |
O2—Cu1—N1—C8 | 146.01 (17) | C3—C4—C5—C6 | 0.3 (4) |
O6—Cu1—N1—C8 | 158.5 (7) | C8—C4—C5—C6 | −179.9 (2) |
O4—Cu1—N1—C8 | −115.68 (16) | O1—C5—C6—C7 | −178.0 (2) |
O2—Cu1—O1—C5 | −115.5 (4) | C4—C5—C6—C7 | 0.6 (4) |
O6—Cu1—O1—C5 | 151.28 (19) | O1—C5—C6—C13 | 6.7 (4) |
N1—Cu1—O1—C5 | −28.55 (19) | C4—C5—C6—C13 | −174.7 (2) |
O4—Cu1—O1—C5 | 52.34 (19) | C3—C2—C7—C6 | 0.2 (4) |
O2—Cu1—O1—Cu2 | 60.5 (4) | C1—C2—C7—C6 | −179.3 (3) |
O6—Cu1—O1—Cu2 | −32.78 (13) | C5—C6—C7—C2 | −0.9 (4) |
N1—Cu1—O1—Cu2 | 147.40 (12) | C13—C6—C7—C2 | 174.3 (3) |
O4—Cu1—O1—Cu2 | −131.71 (11) | C3—C4—C8—N1 | 121.1 (3) |
O1—Cu1—O2—C12 | 65.7 (5) | C5—C4—C8—N1 | −58.7 (3) |
O6—Cu1—O2—C12 | 159.1 (2) | C9—N1—C8—C4 | −60.7 (3) |
N1—Cu1—O2—C12 | −22.52 (19) | C11—N1—C8—C4 | 177.0 (2) |
O4—Cu1—O2—C12 | −102.11 (19) | Cu1—N1—C8—C4 | 63.0 (2) |
O1—Cu1—O4—C10 | −101.58 (17) | C11—N1—C9—C10 | −123.9 (2) |
O2—Cu1—O4—C10 | 76.08 (17) | C8—N1—C9—C10 | 113.8 (2) |
O6—Cu1—O4—C10 | 166.41 (17) | Cu1—N1—C9—C10 | −8.3 (3) |
N1—Cu1—O4—C10 | −6.02 (17) | Cu1—O4—C10—O5 | −175.1 (2) |
C5—O1—Cu2—O11 | 136.56 (17) | Cu1—O4—C10—C9 | 3.1 (3) |
Cu1—O1—Cu2—O11 | −39.65 (13) | N1—C9—C10—O4 | 3.2 (4) |
C5—O1—Cu2—O7 | 40.47 (17) | N1—C9—C10—O5 | −178.5 (2) |
Cu1—O1—Cu2—O7 | −135.74 (12) | C9—N1—C11—C12 | 90.3 (3) |
C5—O1—Cu2—O9 | −128.14 (17) | C8—N1—C11—C12 | −147.0 (2) |
Cu1—O1—Cu2—O9 | 55.65 (12) | Cu1—N1—C11—C12 | −30.0 (2) |
C5—O1—Cu2—N2 | −44.83 (17) | Cu1—O2—C12—O3 | −167.1 (2) |
Cu1—O1—Cu2—N2 | 138.96 (12) | Cu1—O2—C12—C11 | 9.8 (3) |
O11—Cu2—N2—C16 | 48.4 (6) | N1—C11—C12—O3 | −167.6 (2) |
O7—Cu2—N2—C16 | 141.60 (17) | N1—C11—C12—O2 | 15.3 (3) |
O9—Cu2—N2—C16 | −31.06 (16) | C16—N2—C13—C6 | 171.3 (2) |
O1—Cu2—N2—C16 | −123.00 (16) | C14—N2—C13—C6 | −61.3 (3) |
O11—Cu2—N2—C14 | −72.9 (6) | Cu2—N2—C13—C6 | 56.9 (2) |
O7—Cu2—N2—C14 | 20.29 (16) | C7—C6—C13—N2 | 112.9 (3) |
O9—Cu2—N2—C14 | −152.36 (17) | C5—C6—C13—N2 | −71.9 (3) |
O1—Cu2—N2—C14 | 115.70 (16) | C16—N2—C14—C15 | −139.5 (2) |
O11—Cu2—N2—C13 | 165.7 (5) | C13—N2—C14—C15 | 95.9 (3) |
O7—Cu2—N2—C13 | −101.10 (17) | Cu2—N2—C14—C15 | −24.7 (2) |
O9—Cu2—N2—C13 | 86.25 (17) | Cu2—O7—C15—O8 | −176.5 (2) |
O1—Cu2—N2—C13 | −5.69 (17) | Cu2—O7—C15—C14 | 0.4 (3) |
O11—Cu2—O7—C15 | 158.38 (19) | N2—C14—C15—O8 | −165.7 (2) |
O9—Cu2—O7—C15 | 19.5 (4) | N2—C14—C15—O7 | 17.3 (3) |
N2—Cu2—O7—C15 | −12.28 (18) | C14—N2—C16—C17 | 151.8 (2) |
O1—Cu2—O7—C15 | −105.54 (18) | C13—N2—C16—C17 | −82.3 (3) |
O11—Cu2—O9—C17 | −149.28 (19) | Cu2—N2—C16—C17 | 35.8 (3) |
O7—Cu2—O9—C17 | −10.4 (4) | Cu2—O9—C17—O10 | 173.5 (3) |
N2—Cu2—O9—C17 | 21.53 (19) | Cu2—O9—C17—C16 | −5.3 (3) |
O1—Cu2—O9—C17 | 115.01 (18) | N2—C16—C17—O10 | 159.5 (3) |
C7—C2—C3—C4 | 0.8 (4) | N2—C16—C17—O9 | −21.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O15i | 0.82 (4) | 1.72 (4) | 2.533 (3) | 175 (5) |
O6—H6A···O8i | 0.76 (4) | 2.00 (4) | 2.734 (3) | 163 (4) |
O6—H6B···O9 | 0.81 (3) | 1.91 (3) | 2.704 (3) | 167 (3) |
O11—H11C···O3ii | 0.75 (4) | 1.96 (4) | 2.703 (3) | 172 (4) |
O11—H11D···O12 | 0.86 (3) | 1.80 (3) | 2.645 (3) | 167 (3) |
O12—H12A···O14iii | 0.80 (4) | 2.04 (4) | 2.811 (4) | 163 (4) |
O12—H12B···O8iv | 0.90 (4) | 1.89 (4) | 2.787 (3) | 173 (4) |
O13—H13C···O3v | 0.73 (4) | 2.20 (4) | 2.911 (4) | 166 (4) |
O13—H13D···O12 | 0.75 (3) | 2.43 (3) | 3.011 (4) | 135 (4) |
O14—H14C···O15 | 0.79 (4) | 2.16 (4) | 2.896 (4) | 156 (4) |
O14—H14D···O8vi | 0.67 (5) | 2.21 (5) | 2.807 (3) | 149 (5) |
O15—H15A···O10vii | 0.77 (3) | 1.82 (3) | 2.574 (3) | 165 (3) |
O15—H15B···O4viii | 0.94 (4) | 1.87 (4) | 2.790 (3) | 165 (3) |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x, −y, −z; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+1/2, y+1/2, −z+1/2; (v) x+1/2, −y+1/2, z+1/2; (vi) x, y+1, z; (vii) x+1/2, −y+3/2, z+1/2; (viii) −x, −y+1, −z+1. |