Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041991/cv6619sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041991/cv6619Isup2.hkl |
CCDC reference: 296551
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- H-atom completeness 89%
- R factor = 0.032
- wR factor = 0.092
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O1W
Author Response: 'see _publ_section_exptl_refinement' |
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - Cl1 .. 21.77 su
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 5.38 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C1 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C14 PLAT430_ALERT_2_C Short Inter D...A Contact O1W .. O2 .. 2.85 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 84 O1 -CU1 -C15 -C16 23.00 2.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 85 N1 -CU1 -C15 -C16 -173.00 2.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 86 N2 -CU1 -C15 -C16 73.00 2.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 87 O2 -CU1 -C15 -C16 -160.00 2.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 88 CL1 -CU1 -C15 -C16 -57.00 2.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 91 CU1 -C15 -C16 -C17 -130.00 2.00 1.555 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C34 H32 Cl2 Cu2 N4 O4
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C34 H36 Cl2 Cu2 N4 O6 Atom count from the _atom_site data: C34 H32 Cl2 Cu2 N4 O6 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C34 H36 Cl2 Cu2 N4 O6 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 68.00 68.00 0.00 H 72.00 64.00 8.00 Cl 4.00 4.00 0.00 Cu 4.00 4.00 0.00 N 8.00 8.00 0.00 O 12.00 12.00 0.00
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 10 ALERT type 4 Improvement, methodology, query or suggestion
The title compound was prepared according to the literature method of Ding et al. (2005). Pale-green crystals of (I) appeared over a period of one week by slow evaporation of an ethanol solution at room temperature.
The C-bound H atoms were geometrically positioned and refined using a riding model, with C—H bond distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2–1.5 Ueq(C). H atoms of the water molecules were not located in the final difference Fourier map due to the limitations of the data.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
[Cu2(C6H8O4)2Cl2(C14H12N2)2Cl2]·2H2O | F(000) = 816 |
Mr = 794.65 | Dx = 1.604 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2277 (5) Å | Cell parameters from 5751 reflections |
b = 14.9414 (9) Å | θ = 2.7–26.0° |
c = 14.3046 (7) Å | µ = 1.51 mm−1 |
β = 110.639 (3)° | T = 293 K |
V = 1645.65 (16) Å3 | Block, pale green |
Z = 2 | 0.36 × 0.23 × 0.16 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 3224 independent reflections |
Radiation source: fine-focus sealed tube | 2968 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.0° |
ω scans | h = −10→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→18 |
Tmin = 0.613, Tmax = 0.795 | l = −17→17 |
9115 measured reflections |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.7308P] where P = (Fo2 + 2Fc2)/3 |
3224 reflections | (Δ/σ)max = 0.001 |
217 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
[Cu2(C6H8O4)2Cl2(C14H12N2)2Cl2]·2H2O | V = 1645.65 (16) Å3 |
Mr = 794.65 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.2277 (5) Å | µ = 1.51 mm−1 |
b = 14.9414 (9) Å | T = 293 K |
c = 14.3046 (7) Å | 0.36 × 0.23 × 0.16 mm |
β = 110.639 (3)° |
Siemens SMART 1000 CCD area-detector diffractometer | 3224 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2968 reflections with I > 2σ(I) |
Tmin = 0.613, Tmax = 0.795 | Rint = 0.012 |
9115 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.16 | Δρmax = 0.41 e Å−3 |
3224 reflections | Δρmin = −0.32 e Å−3 |
217 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | −0.18963 (4) | −0.071896 (18) | −0.271958 (18) | 0.03706 (12) | |
Cl1 | 0.08458 (8) | −0.14078 (5) | −0.21075 (5) | 0.05367 (18) | |
O1W | −0.0967 (4) | 0.16191 (17) | −0.0246 (2) | 0.0903 (8) | |
O1 | −0.2805 (3) | −0.12699 (13) | −0.17416 (14) | 0.0623 (5) | |
O2 | −0.2128 (3) | 0.01162 (12) | −0.15398 (13) | 0.0537 (5) | |
N1 | −0.1424 (2) | 0.01697 (12) | −0.36347 (12) | 0.0317 (4) | |
N2 | −0.3539 (2) | −0.12626 (11) | −0.40459 (13) | 0.0324 (4) | |
C1 | 0.0535 (3) | 0.11031 (18) | −0.23210 (18) | 0.0480 (6) | |
H1A | 0.0240 | 0.0667 | −0.1914 | 0.072* | |
H1B | 0.0196 | 0.1687 | −0.2178 | 0.072* | |
H1C | 0.1766 | 0.1093 | −0.2178 | 0.072* | |
C2 | −0.0397 (3) | 0.08873 (15) | −0.34023 (17) | 0.0363 (5) | |
C3 | −0.0177 (3) | 0.14332 (15) | −0.41515 (18) | 0.0404 (5) | |
H3A | 0.0535 | 0.1935 | −0.3974 | 0.048* | |
C4 | −0.0999 (3) | 0.12310 (16) | −0.51352 (17) | 0.0405 (5) | |
H4A | −0.0839 | 0.1589 | −0.5628 | 0.049* | |
C5 | −0.2094 (3) | 0.04759 (15) | −0.54019 (16) | 0.0364 (5) | |
C6 | −0.3034 (3) | 0.02153 (17) | −0.64115 (16) | 0.0426 (5) | |
H6A | −0.2918 | 0.0549 | −0.6934 | 0.051* | |
C7 | −0.4086 (3) | −0.05059 (17) | −0.66173 (16) | 0.0434 (5) | |
H7A | −0.4684 | −0.0661 | −0.7280 | 0.052* | |
C8 | −0.4297 (3) | −0.10356 (16) | −0.58392 (16) | 0.0380 (5) | |
C9 | −0.5397 (3) | −0.17867 (17) | −0.60056 (18) | 0.0448 (5) | |
H9A | −0.6016 | −0.1973 | −0.6654 | 0.054* | |
C10 | −0.5551 (3) | −0.22358 (17) | −0.52233 (19) | 0.0458 (6) | |
H10A | −0.6283 | −0.2730 | −0.5338 | 0.055* | |
C11 | −0.4612 (3) | −0.19642 (15) | −0.42285 (17) | 0.0384 (5) | |
C12 | −0.2273 (3) | −0.00340 (14) | −0.46189 (14) | 0.0313 (4) | |
C13 | −0.3385 (3) | −0.07978 (14) | −0.48351 (16) | 0.0325 (4) | |
C14 | −0.4863 (4) | −0.24560 (18) | −0.3380 (2) | 0.0526 (6) | |
H14A | −0.4148 | −0.2192 | −0.2760 | 0.079* | |
H14B | −0.4543 | −0.3072 | −0.3397 | 0.079* | |
H14C | −0.6060 | −0.2420 | −0.3439 | 0.079* | |
C15 | −0.2652 (3) | −0.05726 (17) | −0.12422 (16) | 0.0399 (5) | |
C16 | −0.3109 (4) | −0.0554 (2) | −0.03073 (18) | 0.0510 (6) | |
H16A | −0.2167 | −0.0280 | 0.0231 | 0.061* | |
H16B | −0.3248 | −0.1162 | −0.0110 | 0.061* | |
C17 | −0.4773 (3) | −0.00352 (18) | −0.04705 (16) | 0.0444 (5) | |
H17A | −0.5721 | −0.0327 | −0.0989 | 0.053* | |
H17B | −0.4650 | 0.0562 | −0.0702 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.04360 (19) | 0.04427 (19) | 0.02621 (16) | −0.00489 (11) | 0.01590 (12) | 0.00097 (10) |
Cl1 | 0.0480 (3) | 0.0615 (4) | 0.0514 (4) | 0.0145 (3) | 0.0174 (3) | 0.0183 (3) |
O1W | 0.123 (2) | 0.0695 (15) | 0.0755 (16) | 0.0011 (14) | 0.0319 (15) | −0.0087 (12) |
O1 | 0.0934 (15) | 0.0633 (12) | 0.0435 (10) | −0.0246 (11) | 0.0406 (10) | −0.0092 (9) |
O2 | 0.0782 (13) | 0.0545 (10) | 0.0388 (9) | −0.0056 (9) | 0.0334 (9) | −0.0054 (8) |
N1 | 0.0306 (8) | 0.0387 (9) | 0.0271 (8) | 0.0029 (7) | 0.0117 (7) | 0.0014 (7) |
N2 | 0.0315 (9) | 0.0369 (9) | 0.0298 (9) | 0.0038 (7) | 0.0122 (7) | −0.0019 (7) |
C1 | 0.0492 (14) | 0.0526 (14) | 0.0390 (12) | −0.0119 (11) | 0.0118 (10) | −0.0054 (11) |
C2 | 0.0327 (11) | 0.0418 (11) | 0.0356 (11) | 0.0034 (9) | 0.0136 (9) | 0.0017 (9) |
C3 | 0.0377 (11) | 0.0398 (12) | 0.0469 (13) | 0.0026 (9) | 0.0189 (10) | 0.0055 (9) |
C4 | 0.0437 (12) | 0.0433 (12) | 0.0411 (12) | 0.0099 (10) | 0.0234 (10) | 0.0121 (9) |
C5 | 0.0370 (11) | 0.0439 (12) | 0.0317 (11) | 0.0130 (9) | 0.0166 (9) | 0.0063 (9) |
C6 | 0.0511 (13) | 0.0534 (14) | 0.0272 (10) | 0.0164 (11) | 0.0188 (10) | 0.0084 (9) |
C7 | 0.0444 (13) | 0.0596 (14) | 0.0245 (10) | 0.0134 (11) | 0.0101 (9) | −0.0026 (10) |
C8 | 0.0329 (11) | 0.0499 (12) | 0.0305 (10) | 0.0106 (9) | 0.0105 (8) | −0.0060 (9) |
C9 | 0.0387 (12) | 0.0550 (14) | 0.0375 (12) | 0.0021 (10) | 0.0097 (10) | −0.0158 (10) |
C10 | 0.0402 (12) | 0.0455 (13) | 0.0489 (14) | −0.0027 (10) | 0.0125 (10) | −0.0142 (10) |
C11 | 0.0368 (11) | 0.0369 (11) | 0.0423 (12) | 0.0033 (9) | 0.0150 (9) | −0.0030 (9) |
C12 | 0.0293 (10) | 0.0400 (11) | 0.0269 (10) | 0.0096 (8) | 0.0127 (8) | 0.0025 (8) |
C13 | 0.0301 (10) | 0.0402 (11) | 0.0286 (10) | 0.0084 (8) | 0.0122 (8) | −0.0011 (8) |
C14 | 0.0596 (16) | 0.0452 (13) | 0.0514 (14) | −0.0105 (12) | 0.0177 (12) | 0.0029 (11) |
C15 | 0.0347 (11) | 0.0587 (14) | 0.0285 (11) | 0.0022 (10) | 0.0140 (9) | 0.0035 (10) |
C16 | 0.0538 (15) | 0.0740 (18) | 0.0315 (12) | 0.0070 (12) | 0.0229 (11) | 0.0058 (11) |
C17 | 0.0453 (13) | 0.0640 (15) | 0.0299 (11) | 0.0027 (11) | 0.0205 (10) | 0.0025 (10) |
Cu1—O1 | 1.9828 (17) | C6—C7 | 1.348 (4) |
Cu1—N1 | 1.9966 (17) | C6—H6A | 0.9300 |
Cu1—N2 | 2.0685 (17) | C7—C8 | 1.426 (3) |
Cu1—O2 | 2.1606 (17) | C7—H7A | 0.9300 |
Cu1—Cl1 | 2.3502 (7) | C8—C9 | 1.408 (4) |
Cu1—C15 | 2.414 (2) | C8—C13 | 1.412 (3) |
O1—C15 | 1.244 (3) | C9—C10 | 1.349 (4) |
O2—C15 | 1.247 (3) | C9—H9A | 0.9300 |
N1—C2 | 1.333 (3) | C10—C11 | 1.418 (3) |
N1—C12 | 1.367 (3) | C10—H10A | 0.9300 |
N2—C11 | 1.335 (3) | C11—C14 | 1.494 (3) |
N2—C13 | 1.369 (3) | C12—C13 | 1.427 (3) |
C1—C2 | 1.500 (3) | C14—H14A | 0.9600 |
C1—H1A | 0.9600 | C14—H14B | 0.9600 |
C1—H1B | 0.9600 | C14—H14C | 0.9600 |
C1—H1C | 0.9600 | C15—C16 | 1.512 (3) |
C2—C3 | 1.408 (3) | C16—C17 | 1.518 (4) |
C3—C4 | 1.363 (3) | C16—H16A | 0.9700 |
C3—H3A | 0.9300 | C16—H16B | 0.9700 |
C4—C5 | 1.410 (3) | C17—C17i | 1.522 (4) |
C4—H4A | 0.9300 | C17—H17A | 0.9700 |
C5—C12 | 1.405 (3) | C17—H17B | 0.9700 |
C5—C6 | 1.431 (3) | ||
O1—Cu1—N1 | 161.39 (8) | C6—C7—H7A | 119.4 |
O1—Cu1—N2 | 101.36 (8) | C8—C7—H7A | 119.4 |
N1—Cu1—N2 | 82.83 (7) | C9—C8—C13 | 116.9 (2) |
O1—Cu1—O2 | 61.94 (7) | C9—C8—C7 | 124.0 (2) |
N1—Cu1—O2 | 102.66 (7) | C13—C8—C7 | 119.2 (2) |
N2—Cu1—O2 | 137.23 (7) | C10—C9—C8 | 119.9 (2) |
O1—Cu1—Cl1 | 96.12 (7) | C10—C9—H9A | 120.0 |
N1—Cu1—Cl1 | 98.76 (5) | C8—C9—H9A | 120.0 |
N2—Cu1—Cl1 | 113.64 (5) | C9—C10—C11 | 120.8 (2) |
O2—Cu1—Cl1 | 107.42 (6) | C9—C10—H10A | 119.6 |
O1—Cu1—C15 | 30.94 (8) | C11—C10—H10A | 119.6 |
N1—Cu1—C15 | 133.12 (8) | N2—C11—C10 | 120.6 (2) |
N2—Cu1—C15 | 123.50 (7) | N2—C11—C14 | 119.9 (2) |
O2—Cu1—C15 | 31.02 (7) | C10—C11—C14 | 119.4 (2) |
Cl1—Cu1—C15 | 102.89 (6) | N1—C12—C5 | 122.8 (2) |
C15—O1—Cu1 | 94.03 (14) | N1—C12—C13 | 117.21 (18) |
C15—O2—Cu1 | 85.77 (14) | C5—C12—C13 | 120.03 (19) |
C2—N1—C12 | 119.00 (18) | N2—C13—C8 | 122.7 (2) |
C2—N1—Cu1 | 128.64 (14) | N2—C13—C12 | 117.76 (18) |
C12—N1—Cu1 | 112.34 (14) | C8—C13—C12 | 119.5 (2) |
C11—N2—C13 | 118.94 (18) | C11—C14—H14A | 109.5 |
C11—N2—Cu1 | 131.36 (15) | C11—C14—H14B | 109.5 |
C13—N2—Cu1 | 109.67 (14) | H14A—C14—H14B | 109.5 |
C2—C1—H1A | 109.5 | C11—C14—H14C | 109.5 |
C2—C1—H1B | 109.5 | H14A—C14—H14C | 109.5 |
H1A—C1—H1B | 109.5 | H14B—C14—H14C | 109.5 |
C2—C1—H1C | 109.5 | O1—C15—O2 | 118.2 (2) |
H1A—C1—H1C | 109.5 | O1—C15—C16 | 121.1 (2) |
H1B—C1—H1C | 109.5 | O2—C15—C16 | 120.7 (2) |
N1—C2—C3 | 121.1 (2) | O1—C15—Cu1 | 55.02 (11) |
N1—C2—C1 | 118.6 (2) | O2—C15—Cu1 | 63.21 (12) |
C3—C2—C1 | 120.3 (2) | C16—C15—Cu1 | 175.82 (19) |
C4—C3—C2 | 120.5 (2) | C15—C16—C17 | 111.4 (2) |
C4—C3—H3A | 119.8 | C15—C16—H16A | 109.3 |
C2—C3—H3A | 119.8 | C17—C16—H16A | 109.3 |
C3—C4—C5 | 119.6 (2) | C15—C16—H16B | 109.3 |
C3—C4—H4A | 120.2 | C17—C16—H16B | 109.3 |
C5—C4—H4A | 120.2 | H16A—C16—H16B | 108.0 |
C12—C5—C4 | 117.1 (2) | C16—C17—C17i | 112.8 (3) |
C12—C5—C6 | 119.1 (2) | C16—C17—H17A | 109.0 |
C4—C5—C6 | 123.9 (2) | C17i—C17—H17A | 109.0 |
C7—C6—C5 | 121.0 (2) | C16—C17—H17B | 109.0 |
C7—C6—H6A | 119.5 | C17i—C17—H17B | 109.0 |
C5—C6—H6A | 119.5 | H17A—C17—H17B | 107.8 |
C6—C7—C8 | 121.3 (2) | ||
N1—Cu1—O1—C15 | −38.0 (3) | Cu1—N2—C11—C10 | −176.62 (16) |
N2—Cu1—O1—C15 | −139.42 (16) | C13—N2—C11—C14 | −177.2 (2) |
O2—Cu1—O1—C15 | −1.57 (15) | Cu1—N2—C11—C14 | 4.9 (3) |
Cl1—Cu1—O1—C15 | 104.93 (16) | C9—C10—C11—N2 | −0.7 (3) |
O1—Cu1—O2—C15 | 1.57 (15) | C9—C10—C11—C14 | 177.8 (2) |
N1—Cu1—O2—C15 | 170.36 (14) | C2—N1—C12—C5 | 0.9 (3) |
N2—Cu1—O2—C15 | 77.24 (17) | Cu1—N1—C12—C5 | −177.71 (15) |
Cl1—Cu1—O2—C15 | −86.10 (14) | C2—N1—C12—C13 | −178.83 (18) |
O1—Cu1—N1—C2 | 73.7 (3) | Cu1—N1—C12—C13 | 2.6 (2) |
N2—Cu1—N1—C2 | 178.06 (19) | C4—C5—C12—N1 | −0.8 (3) |
O2—Cu1—N1—C2 | 41.17 (19) | C6—C5—C12—N1 | −179.89 (18) |
Cl1—Cu1—N1—C2 | −69.01 (18) | C4—C5—C12—C13 | 178.88 (18) |
C15—Cu1—N1—C2 | 48.0 (2) | C6—C5—C12—C13 | −0.2 (3) |
O1—Cu1—N1—C12 | −107.9 (3) | C11—N2—C13—C8 | −0.8 (3) |
N2—Cu1—N1—C12 | −3.54 (13) | Cu1—N2—C13—C8 | 177.45 (15) |
O2—Cu1—N1—C12 | −140.44 (14) | C11—N2—C13—C12 | 178.03 (18) |
Cl1—Cu1—N1—C12 | 109.38 (13) | Cu1—N2—C13—C12 | −3.7 (2) |
C15—Cu1—N1—C12 | −133.65 (14) | C9—C8—C13—N2 | −0.1 (3) |
O1—Cu1—N2—C11 | −16.5 (2) | C7—C8—C13—N2 | 178.90 (19) |
N1—Cu1—N2—C11 | −178.10 (19) | C9—C8—C13—C12 | −178.96 (19) |
O2—Cu1—N2—C11 | −77.2 (2) | C7—C8—C13—C12 | 0.1 (3) |
Cl1—Cu1—N2—C11 | 85.45 (18) | N1—C12—C13—N2 | 0.9 (3) |
C15—Cu1—N2—C11 | −40.1 (2) | C5—C12—C13—N2 | −178.83 (17) |
O1—Cu1—N2—C13 | 165.52 (14) | N1—C12—C13—C8 | 179.77 (18) |
N1—Cu1—N2—C13 | 3.90 (13) | C5—C12—C13—C8 | 0.1 (3) |
O2—Cu1—N2—C13 | 104.81 (15) | Cu1—O1—C15—O2 | 2.7 (3) |
Cl1—Cu1—N2—C13 | −92.56 (13) | Cu1—O1—C15—C16 | −178.10 (19) |
C15—Cu1—N2—C13 | 141.87 (13) | Cu1—O2—C15—O1 | −2.5 (2) |
C12—N1—C2—C3 | −0.1 (3) | Cu1—O2—C15—C16 | 178.3 (2) |
Cu1—N1—C2—C3 | 178.24 (15) | N1—Cu1—C15—O1 | 164.38 (16) |
C12—N1—C2—C1 | −179.73 (19) | N2—Cu1—C15—O1 | 49.88 (19) |
Cu1—N1—C2—C1 | −1.4 (3) | O2—Cu1—C15—O1 | 177.3 (2) |
N1—C2—C3—C4 | −0.8 (3) | Cl1—Cu1—C15—O1 | −80.26 (17) |
C1—C2—C3—C4 | 178.9 (2) | O1—Cu1—C15—O2 | −177.3 (2) |
C2—C3—C4—C5 | 0.8 (3) | N1—Cu1—C15—O2 | −12.93 (19) |
C3—C4—C5—C12 | 0.0 (3) | N2—Cu1—C15—O2 | −127.43 (14) |
C3—C4—C5—C6 | 179.0 (2) | Cl1—Cu1—C15—O2 | 102.43 (14) |
C12—C5—C6—C7 | 0.2 (3) | O1—Cu1—C15—C16 | 23 (2) |
C4—C5—C6—C7 | −178.8 (2) | N1—Cu1—C15—C16 | −173 (2) |
C5—C6—C7—C8 | −0.1 (3) | N2—Cu1—C15—C16 | 73 (2) |
C6—C7—C8—C9 | 178.9 (2) | O2—Cu1—C15—C16 | −160 (2) |
C6—C7—C8—C13 | 0.0 (3) | Cl1—Cu1—C15—C16 | −57 (2) |
C13—C8—C9—C10 | 0.7 (3) | O1—C15—C16—C17 | −108.1 (3) |
C7—C8—C9—C10 | −178.3 (2) | O2—C15—C16—C17 | 71.1 (3) |
C8—C9—C10—C11 | −0.3 (4) | Cu1—C15—C16—C17 | −130 (2) |
C13—N2—C11—C10 | 1.2 (3) | C15—C16—C17—C17i | −177.2 (3) |
Symmetry code: (i) −x−1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C6H8O4)2Cl2(C14H12N2)2Cl2]·2H2O |
Mr | 794.65 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.2277 (5), 14.9414 (9), 14.3046 (7) |
β (°) | 110.639 (3) |
V (Å3) | 1645.65 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.51 |
Crystal size (mm) | 0.36 × 0.23 × 0.16 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.613, 0.795 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9115, 3224, 2968 |
Rint | 0.012 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.092, 1.16 |
No. of reflections | 3224 |
No. of parameters | 217 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.32 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Cu1—O1 | 1.9828 (17) | Cu1—O2 | 2.1606 (17) |
Cu1—N1 | 1.9966 (17) | Cu1—Cl1 | 2.3502 (7) |
Cu1—N2 | 2.0685 (17) |
In our ongoing studies of adipate–metal complexes, the title compound, (I), was obtained. The present X-ray crystallographic analysis was undertaken in order to establish the stereochemistry of (I).
The binuclear copper complex in (I) possesses a crystallographically imposed centre of symmetry (Fig. 1). Each CuII atom is five-coordinated by two N atoms from one 9,10-dimethyl-phenanthroline ligand, two O atoms from one adipate anion and one Cl atom (Table 1). This CuO2N2Cl coordination forms a distorted tetragonal–pyramidal geometry. The axial position is occupied by the Cl atom, with a Cu—Cl distance of 2.350 (1) Å. The N and O atoms form the square plane.
In the crystal structure (Fig. 2), the short interplanar distances of 3.328 and 3.371 Å between the mean planes of neighbouring phenanthroline moieties suggest strong π···π interactions. The distances between the centroids of rings N1/C2–C5/C12 (Cg1), N2/C8–C11/C13 (Cg2) and C5–C8/C12/C13 (Cg3) are Cg1···Cg2i = 3.562 (1), Cg1···Cg3ii = 3.685 (1) and Cg2···Cg3i = 3.609 (1) Å [symmetry codes: (i) −1 − x, −y, −1 − z; (ii) −x, −y, −1 − z]. The molecules of (I) form stacks via these π–π interactions, which are arranged in layers parallel to the ac plane. There are two types of layer, which differ in the direction of the normal to the phenanthroline moieties. The crystal structure is built up from alternating layers of these two types.