Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061193/hk2390sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061193/hk2390Isup2.hkl |
CCDC reference: 1303500
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.006 Å
- R factor = 0.047
- wR factor = 0.143
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H3A .. H4B .. 1.88 Ang. PLAT420_ALERT_2_B D-H Without Acceptor O2 - H2A ... ? PLAT420_ALERT_2_B D-H Without Acceptor O3 - H3A ... ? PLAT420_ALERT_2_B D-H Without Acceptor O4 - H4A ... ?
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N7 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N8 PLAT245_ALERT_2_C U(iso) H3A Smaller than U(eq) O3 by ... 0.05 AngSq PLAT414_ALERT_2_C Short Intra D-H..H-X H2A .. H27A .. 1.95 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. N2 .. 2.84 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H28A .. O7 .. 2.63 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for O1 .. N2 .. 94.00 Deg.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 13
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 3 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Copper (II) nitrate pentahydrate (295.5 mg, 1 mmol), phen (180.2 mg, 1 mmol), dimethyl glyoxime (116.2 mg, 1 mmol) and distilled water (8 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small blue crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.
H atoms (for H2O) were located in a difference synthesis and refined isotropically [O—H = 0.811 (18)–0.880 (18) Å and Uiso(H) = 0.460 (7)–0.585 (10) Å2]. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.2 for aromatic H, and x = 1.5 for all other H atoms.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).
[Cu(C12H8N2)2(C4H8N2O2)](NO3)2·2H2O | F(000) = 1444 |
Mr = 700.13 | Dx = 1.536 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6015 reflections |
a = 13.8102 (12) Å | θ = 2.1–25.0° |
b = 11.9816 (11) Å | µ = 0.79 mm−1 |
c = 18.4018 (14) Å | T = 273 K |
β = 96.204 (2)° | Prism, blue |
V = 3027.1 (4) Å3 | 0.31 × 0.22 × 0.19 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 6368 independent reflections |
Radiation source: fine-focus sealed tube | 3102 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ϕ and ω scans | θmax = 27.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.794, Tmax = 0.867 | k = −15→15 |
20447 measured reflections | l = −22→23 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.059P)2] where P = (Fo2 + 2Fc2)/3 |
6368 reflections | (Δ/σ)max = 0.003 |
444 parameters | Δρmax = 0.58 e Å−3 |
13 restraints | Δρmin = −0.53 e Å−3 |
[Cu(C12H8N2)2(C4H8N2O2)](NO3)2·2H2O | V = 3027.1 (4) Å3 |
Mr = 700.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.8102 (12) Å | µ = 0.79 mm−1 |
b = 11.9816 (11) Å | T = 273 K |
c = 18.4018 (14) Å | 0.31 × 0.22 × 0.19 mm |
β = 96.204 (2)° |
Bruker SMART CCD area-detector diffractometer | 6368 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3102 reflections with I > 2σ(I) |
Tmin = 0.794, Tmax = 0.867 | Rint = 0.042 |
20447 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 13 restraints |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.58 e Å−3 |
6368 reflections | Δρmin = −0.53 e Å−3 |
444 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 | 0.77578 (3) | 0.75557 (4) | 0.03822 (3) | 0.04339 (18) | |
O1 | 0.7959 (2) | 0.9963 (2) | 0.04784 (15) | 0.0477 (7) | |
H1A | 0.8164 | 1.0029 | 0.0079 | 0.072* | |
O2 | 0.8348 (2) | 0.6027 (2) | 0.14811 (16) | 0.0540 (8) | |
H2A | 0.8278 | 0.5985 | 0.1917 | 0.081* | |
O3 | 0.5555 (11) | 0.4274 (14) | 0.1403 (10) | 0.508 (12) | |
H3A | 0.5564 (19) | 0.4911 (16) | 0.1554 (17) | 0.460 (7)* | |
H3B | 0.502 (2) | 0.397 (2) | 0.119 (2) | 0.511 (11)* | |
O4 | 0.3053 (16) | 0.665 (2) | 0.7978 (7) | 0.580 (18) | |
H4A | 0.272 (2) | 0.670 (3) | 0.8355 (17) | 0.585 (10)* | |
H4B | 0.346 (9) | 0.612 (11) | 0.811 (6) | 0.58 (8)* | |
O5 | 0.7740 (2) | 0.1305 (3) | 0.9095 (2) | 0.0815 (11) | |
O6 | 0.8929 (2) | 0.0157 (3) | 0.92842 (18) | 0.0651 (9) | |
O7 | 0.8888 (3) | 0.1350 (4) | 0.8436 (3) | 0.1145 (16) | |
O8 | 0.7391 (5) | 0.8777 (6) | 0.2887 (3) | 0.164 (2) | |
O9 | 0.6155 (6) | 0.8839 (6) | 0.3362 (4) | 0.191 (3) | |
O10 | 0.6400 (7) | 1.0072 (6) | 0.2626 (5) | 0.329 (9) | |
N1 | 0.6536 (2) | 0.7798 (2) | 0.07648 (19) | 0.0366 (8) | |
N2 | 0.7070 (2) | 0.8183 (2) | −0.05350 (18) | 0.0356 (8) | |
N3 | 0.7386 (2) | 0.6061 (2) | 0.00380 (18) | 0.0395 (8) | |
N4 | 0.8933 (2) | 0.7246 (2) | −0.00692 (17) | 0.0330 (7) | |
N5 | 0.8370 (2) | 0.7042 (3) | 0.12949 (18) | 0.0383 (8) | |
N6 | 0.8219 (2) | 0.8938 (2) | 0.07669 (18) | 0.0343 (8) | |
N7 | 0.8516 (3) | 0.0927 (3) | 0.8921 (2) | 0.0582 (10) | |
N8 | 0.6663 (5) | 0.9304 (8) | 0.2888 (5) | 0.132 (3) | |
C1 | 0.6306 (3) | 0.7623 (3) | 0.1435 (2) | 0.0485 (11) | |
H1 | 0.6785 | 0.7366 | 0.1790 | 0.058* | |
C2 | 0.5363 (3) | 0.7812 (4) | 0.1628 (3) | 0.0607 (13) | |
H2 | 0.5224 | 0.7687 | 0.2104 | 0.073* | |
C3 | 0.4661 (3) | 0.8177 (4) | 0.1117 (3) | 0.0546 (12) | |
H3 | 0.4033 | 0.8292 | 0.1240 | 0.066* | |
C4 | 0.4875 (3) | 0.8382 (3) | 0.0407 (3) | 0.0449 (11) | |
C5 | 0.4208 (3) | 0.8803 (4) | −0.0175 (3) | 0.0615 (14) | |
H5 | 0.3566 | 0.8935 | −0.0090 | 0.074* | |
C6 | 0.4482 (3) | 0.9016 (4) | −0.0850 (3) | 0.0611 (13) | |
H6 | 0.4023 | 0.9284 | −0.1216 | 0.073* | |
C7 | 0.5458 (3) | 0.8837 (3) | −0.1006 (3) | 0.0479 (11) | |
C8 | 0.5806 (4) | 0.9062 (3) | −0.1657 (3) | 0.0579 (13) | |
H8 | 0.5389 | 0.9352 | −0.2042 | 0.069* | |
C9 | 0.6759 (4) | 0.8867 (3) | −0.1750 (3) | 0.0583 (13) | |
H9 | 0.6999 | 0.9039 | −0.2189 | 0.070* | |
C10 | 0.7368 (3) | 0.8403 (3) | −0.1170 (2) | 0.0449 (11) | |
H10 | 0.8011 | 0.8245 | −0.1239 | 0.054* | |
C11 | 0.6125 (3) | 0.8403 (3) | −0.0440 (2) | 0.0402 (10) | |
C12 | 0.5832 (3) | 0.8181 (3) | 0.0254 (2) | 0.0367 (9) | |
C13 | 0.6603 (3) | 0.5464 (4) | 0.0144 (3) | 0.0557 (12) | |
H13 | 0.6143 | 0.5757 | 0.0424 | 0.067* | |
C14 | 0.6465 (3) | 0.4411 (4) | −0.0158 (3) | 0.0693 (15) | |
H14 | 0.5902 | 0.4017 | −0.0087 | 0.083* | |
C15 | 0.7126 (4) | 0.3944 (4) | −0.0551 (3) | 0.0630 (14) | |
H15 | 0.7025 | 0.3232 | −0.0746 | 0.076* | |
C16 | 0.7965 (3) | 0.4544 (3) | −0.0661 (2) | 0.0454 (11) | |
C17 | 0.8721 (3) | 0.4153 (4) | −0.1060 (2) | 0.0518 (12) | |
H17 | 0.8656 | 0.3463 | −0.1291 | 0.062* | |
C18 | 0.9519 (3) | 0.4752 (4) | −0.1111 (2) | 0.0518 (12) | |
H18 | 1.0005 | 0.4466 | −0.1371 | 0.062* | |
C19 | 0.9649 (3) | 0.5826 (3) | −0.0776 (2) | 0.0413 (10) | |
C20 | 1.0478 (3) | 0.6513 (4) | −0.0800 (2) | 0.0485 (11) | |
H20 | 1.0997 | 0.6279 | −0.1044 | 0.058* | |
C21 | 1.0503 (3) | 0.7505 (4) | −0.0466 (2) | 0.0483 (10) | |
H21 | 1.1046 | 0.7961 | −0.0477 | 0.058* | |
C22 | 0.9718 (3) | 0.7865 (3) | −0.0099 (2) | 0.0425 (10) | |
H22 | 0.9753 | 0.8559 | 0.0128 | 0.051* | |
C23 | 0.8911 (3) | 0.6242 (3) | −0.0406 (2) | 0.0360 (9) | |
C24 | 0.8063 (3) | 0.5595 (3) | −0.0345 (2) | 0.0360 (9) | |
C25 | 0.8806 (3) | 0.7818 (3) | 0.1719 (2) | 0.0404 (10) | |
C26 | 0.8678 (3) | 0.8924 (3) | 0.1411 (2) | 0.0424 (10) | |
C27 | 0.9330 (3) | 0.7564 (4) | 0.2448 (2) | 0.0625 (13) | |
H27A | 0.9257 | 0.6786 | 0.2556 | 0.094* | |
H27B | 0.9063 | 0.8005 | 0.2814 | 0.094* | |
H27C | 1.0008 | 0.7736 | 0.2446 | 0.094* | |
C28 | 0.9050 (3) | 0.9928 (4) | 0.1832 (3) | 0.0655 (14) | |
H28A | 0.9691 | 0.9777 | 0.2069 | 0.098* | |
H28B | 0.8622 | 1.0104 | 0.2193 | 0.098* | |
H28C | 0.9078 | 1.0548 | 0.1505 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0398 (3) | 0.0422 (3) | 0.0474 (3) | 0.0021 (2) | 0.0012 (2) | −0.0023 (3) |
O1 | 0.0571 (18) | 0.0342 (15) | 0.051 (2) | 0.0071 (13) | 0.0022 (15) | −0.0008 (14) |
O2 | 0.0619 (19) | 0.0469 (19) | 0.052 (2) | 0.0035 (14) | 0.0016 (16) | 0.0154 (15) |
O3 | 0.43 (2) | 0.68 (3) | 0.48 (2) | 0.07 (2) | 0.37 (2) | 0.14 (2) |
O4 | 0.47 (3) | 0.92 (5) | 0.33 (2) | 0.09 (3) | −0.065 (17) | −0.35 (2) |
O5 | 0.059 (2) | 0.082 (3) | 0.105 (3) | 0.0161 (19) | 0.017 (2) | 0.008 (2) |
O6 | 0.064 (2) | 0.0503 (19) | 0.080 (3) | 0.0093 (16) | 0.0021 (18) | 0.0147 (18) |
O7 | 0.107 (3) | 0.120 (4) | 0.125 (4) | 0.032 (3) | 0.055 (3) | 0.059 (3) |
O8 | 0.158 (5) | 0.171 (6) | 0.158 (6) | −0.022 (5) | −0.004 (5) | −0.018 (4) |
O9 | 0.243 (9) | 0.178 (6) | 0.150 (7) | −0.005 (6) | 0.007 (6) | −0.012 (5) |
O10 | 0.433 (15) | 0.123 (5) | 0.356 (13) | −0.061 (6) | −0.305 (11) | 0.106 (6) |
N1 | 0.0351 (18) | 0.0340 (18) | 0.040 (2) | 0.0010 (13) | −0.0003 (15) | 0.0014 (15) |
N2 | 0.038 (2) | 0.0291 (18) | 0.039 (2) | 0.0021 (14) | −0.0014 (15) | −0.0052 (15) |
N3 | 0.0348 (18) | 0.0357 (18) | 0.047 (2) | 0.0007 (15) | 0.0007 (16) | 0.0009 (16) |
N4 | 0.0282 (17) | 0.0293 (18) | 0.040 (2) | 0.0027 (13) | −0.0033 (14) | −0.0009 (14) |
N5 | 0.0318 (18) | 0.0396 (19) | 0.044 (2) | 0.0048 (15) | 0.0046 (15) | 0.0028 (17) |
N6 | 0.0318 (17) | 0.0326 (18) | 0.038 (2) | 0.0025 (14) | 0.0020 (15) | −0.0013 (15) |
N7 | 0.052 (3) | 0.056 (3) | 0.068 (3) | −0.008 (2) | 0.010 (2) | 0.009 (2) |
N8 | 0.089 (5) | 0.176 (9) | 0.123 (7) | −0.005 (5) | −0.021 (5) | −0.079 (7) |
C1 | 0.038 (2) | 0.057 (3) | 0.050 (3) | 0.009 (2) | 0.0039 (19) | 0.004 (2) |
C2 | 0.057 (3) | 0.069 (3) | 0.059 (3) | 0.000 (2) | 0.021 (3) | −0.001 (3) |
C3 | 0.033 (2) | 0.054 (3) | 0.078 (4) | 0.000 (2) | 0.013 (2) | −0.016 (3) |
C4 | 0.035 (2) | 0.033 (2) | 0.066 (3) | 0.0021 (18) | −0.002 (2) | −0.006 (2) |
C5 | 0.033 (2) | 0.051 (3) | 0.098 (5) | 0.007 (2) | −0.005 (3) | −0.007 (3) |
C6 | 0.052 (3) | 0.048 (3) | 0.077 (4) | 0.010 (2) | −0.020 (3) | −0.004 (3) |
C7 | 0.050 (3) | 0.036 (2) | 0.053 (3) | 0.003 (2) | −0.015 (2) | −0.005 (2) |
C8 | 0.072 (3) | 0.046 (3) | 0.051 (4) | 0.008 (2) | −0.018 (3) | 0.001 (2) |
C9 | 0.091 (4) | 0.042 (3) | 0.039 (3) | −0.002 (2) | −0.007 (3) | 0.000 (2) |
C10 | 0.056 (3) | 0.040 (2) | 0.038 (3) | 0.001 (2) | 0.003 (2) | −0.006 (2) |
C11 | 0.043 (3) | 0.026 (2) | 0.048 (3) | 0.0012 (17) | −0.010 (2) | −0.0047 (19) |
C12 | 0.035 (2) | 0.028 (2) | 0.046 (3) | −0.0028 (17) | 0.0000 (19) | −0.0025 (19) |
C13 | 0.042 (3) | 0.042 (3) | 0.084 (4) | −0.003 (2) | 0.009 (2) | −0.007 (2) |
C14 | 0.053 (3) | 0.045 (3) | 0.109 (5) | −0.017 (2) | 0.004 (3) | −0.008 (3) |
C15 | 0.066 (3) | 0.035 (2) | 0.085 (4) | −0.006 (2) | −0.005 (3) | −0.011 (2) |
C16 | 0.051 (3) | 0.034 (2) | 0.048 (3) | 0.006 (2) | −0.010 (2) | −0.001 (2) |
C17 | 0.070 (3) | 0.039 (3) | 0.044 (3) | 0.011 (2) | −0.005 (2) | −0.005 (2) |
C18 | 0.069 (3) | 0.050 (3) | 0.035 (3) | 0.029 (2) | 0.003 (2) | −0.005 (2) |
C19 | 0.046 (3) | 0.045 (2) | 0.032 (3) | 0.013 (2) | −0.0020 (19) | 0.002 (2) |
C20 | 0.042 (3) | 0.065 (3) | 0.040 (3) | 0.011 (2) | 0.008 (2) | 0.002 (2) |
C21 | 0.036 (2) | 0.057 (3) | 0.052 (3) | −0.003 (2) | 0.0042 (19) | 0.004 (3) |
C22 | 0.042 (3) | 0.037 (2) | 0.047 (3) | 0.0025 (18) | −0.001 (2) | −0.0027 (19) |
C23 | 0.037 (2) | 0.038 (2) | 0.032 (2) | 0.0078 (18) | −0.0040 (18) | 0.0026 (19) |
C24 | 0.041 (2) | 0.031 (2) | 0.034 (3) | 0.0058 (18) | −0.0033 (18) | −0.0009 (18) |
C25 | 0.036 (2) | 0.051 (3) | 0.034 (3) | 0.0035 (19) | 0.0040 (18) | 0.003 (2) |
C26 | 0.038 (2) | 0.042 (2) | 0.047 (3) | −0.0004 (19) | 0.007 (2) | −0.013 (2) |
C27 | 0.058 (3) | 0.078 (3) | 0.048 (3) | −0.003 (3) | −0.011 (2) | 0.006 (3) |
C28 | 0.072 (3) | 0.057 (3) | 0.065 (4) | −0.006 (2) | −0.007 (3) | −0.022 (3) |
Cu1—N1 | 1.919 (3) | C8—C9 | 1.365 (6) |
Cu1—N2 | 1.992 (3) | C8—H8 | 0.9300 |
Cu1—N3 | 1.950 (3) | C9—C10 | 1.401 (6) |
Cu1—N4 | 1.937 (3) | C9—H9 | 0.9300 |
Cu1—N5 | 1.899 (3) | C10—H10 | 0.9300 |
Cu1—N6 | 1.885 (3) | C11—C12 | 1.406 (5) |
O1—N6 | 1.370 (4) | C13—C14 | 1.382 (6) |
O1—H1A | 0.8200 | C13—H13 | 0.9300 |
O2—N5 | 1.265 (4) | C14—C15 | 1.346 (6) |
O2—H2A | 0.8200 | C14—H14 | 0.9300 |
O5—N7 | 1.236 (4) | C15—C16 | 1.398 (6) |
O6—N7 | 1.242 (4) | C15—H15 | 0.9300 |
O7—N7 | 1.190 (5) | C16—C24 | 1.386 (5) |
O8—N8 | 1.188 (7) | C16—C17 | 1.419 (6) |
O9—N8 | 1.303 (9) | C17—C18 | 1.326 (6) |
O10—N8 | 1.083 (9) | C17—H17 | 0.9300 |
N1—C1 | 1.322 (5) | C18—C19 | 1.430 (5) |
N1—C12 | 1.358 (5) | C18—H18 | 0.9300 |
N2—C10 | 1.307 (5) | C19—C23 | 1.379 (5) |
N2—C11 | 1.360 (5) | C19—C20 | 1.415 (5) |
N3—C13 | 1.328 (5) | C20—C21 | 1.336 (5) |
N3—C24 | 1.352 (5) | C20—H20 | 0.9300 |
N4—C22 | 1.320 (5) | C21—C22 | 1.405 (5) |
N4—C23 | 1.353 (4) | C21—H21 | 0.9300 |
N5—C25 | 1.317 (5) | C22—H22 | 0.9300 |
N6—C26 | 1.283 (5) | C23—C24 | 1.419 (5) |
C1—C2 | 1.405 (5) | C25—C26 | 1.445 (5) |
C1—H1 | 0.9300 | C25—C27 | 1.485 (5) |
C2—C3 | 1.347 (6) | C26—C28 | 1.492 (5) |
C2—H2 | 0.9300 | C27—H27A | 0.9600 |
C3—C4 | 1.393 (6) | C27—H27B | 0.9600 |
C3—H3 | 0.9300 | C27—H27C | 0.9600 |
C4—C12 | 1.401 (5) | C28—H28A | 0.9600 |
C4—C5 | 1.426 (6) | C28—H28B | 0.9600 |
C5—C6 | 1.362 (6) | C28—H28C | 0.9600 |
C5—H5 | 0.9300 | O3—H3A | 0.811 (18) |
C6—C7 | 1.425 (6) | O3—H3B | 0.880 (18) |
C6—H6 | 0.9300 | O4—H4B | 0.87 (13) |
C7—C8 | 1.365 (6) | O4—H4A | 0.876 (19) |
C7—C11 | 1.413 (5) | ||
N1—Cu1—N2 | 84.03 (14) | C10—C9—H9 | 120.6 |
N1—Cu1—N3 | 92.68 (13) | N2—C10—C9 | 122.6 (4) |
N1—Cu1—N4 | 175.34 (13) | N2—C10—H10 | 118.7 |
N1—Cu1—N5 | 92.83 (13) | C9—C10—H10 | 118.7 |
N1—Cu1—N6 | 90.22 (12) | N2—C11—C12 | 117.0 (3) |
N2—Cu1—N3 | 89.24 (12) | N2—C11—C7 | 122.3 (4) |
N2—Cu1—N4 | 93.09 (13) | C12—C11—C7 | 120.7 (4) |
N2—Cu1—N5 | 175.75 (13) | N1—C12—C4 | 122.6 (4) |
N2—Cu1—N6 | 95.58 (13) | N1—C12—C11 | 116.0 (3) |
N3—Cu1—N4 | 83.61 (13) | C4—C12—C11 | 121.4 (4) |
N3—Cu1—N5 | 93.78 (14) | N3—C13—C14 | 120.8 (4) |
N3—Cu1—N6 | 174.62 (13) | N3—C13—H13 | 119.6 |
N4—Cu1—N5 | 90.22 (12) | C14—C13—H13 | 119.6 |
N4—Cu1—N6 | 93.71 (12) | C15—C14—C13 | 121.5 (4) |
N5—Cu1—N6 | 81.54 (14) | C15—C14—H14 | 119.2 |
N6—O1—H1A | 109.5 | C13—C14—H14 | 119.2 |
N5—O2—H2A | 109.5 | C14—C15—C16 | 119.0 (4) |
C1—N1—C12 | 118.2 (3) | C14—C15—H15 | 120.5 |
C1—N1—Cu1 | 128.8 (3) | C16—C15—H15 | 120.5 |
C12—N1—Cu1 | 112.9 (3) | C24—C16—C15 | 116.8 (4) |
C10—N2—C11 | 118.4 (3) | C24—C16—C17 | 118.2 (4) |
C10—N2—Cu1 | 131.7 (3) | C15—C16—C17 | 125.0 (4) |
C11—N2—Cu1 | 109.9 (3) | C18—C17—C16 | 121.4 (4) |
C13—N3—C24 | 118.3 (3) | C18—C17—H17 | 119.3 |
C13—N3—Cu1 | 129.6 (3) | C16—C17—H17 | 119.3 |
C24—N3—Cu1 | 112.1 (2) | C17—C18—C19 | 121.5 (4) |
C22—N4—C23 | 117.3 (3) | C17—C18—H18 | 119.2 |
C22—N4—Cu1 | 129.9 (3) | C19—C18—H18 | 119.2 |
C23—N4—Cu1 | 112.9 (2) | C23—C19—C20 | 116.7 (4) |
O2—N5—C25 | 122.7 (3) | C23—C19—C18 | 118.2 (4) |
O2—N5—Cu1 | 122.0 (3) | C20—C19—C18 | 125.1 (4) |
C25—N5—Cu1 | 115.3 (3) | C21—C20—C19 | 119.0 (4) |
C26—N6—O1 | 116.9 (3) | C21—C20—H20 | 120.5 |
C26—N6—Cu1 | 116.6 (3) | C19—C20—H20 | 120.5 |
O1—N6—Cu1 | 125.4 (2) | C20—C21—C22 | 120.7 (4) |
O7—N7—O5 | 119.6 (4) | C20—C21—H21 | 119.6 |
O7—N7—O6 | 120.6 (4) | C22—C21—H21 | 119.6 |
O5—N7—O6 | 119.6 (4) | N4—C22—C21 | 121.8 (4) |
O10—N8—O8 | 133.9 (12) | N4—C22—H22 | 119.1 |
O10—N8—O9 | 118.9 (10) | C21—C22—H22 | 119.1 |
O8—N8—O9 | 106.9 (10) | N4—C23—C19 | 124.5 (4) |
N1—C1—C2 | 122.2 (4) | N4—C23—C24 | 115.3 (3) |
N1—C1—H1 | 118.9 | C19—C23—C24 | 120.1 (4) |
C2—C1—H1 | 118.9 | N3—C24—C16 | 123.5 (4) |
C3—C2—C1 | 119.5 (4) | N3—C24—C23 | 116.0 (3) |
C3—C2—H2 | 120.2 | C16—C24—C23 | 120.4 (4) |
C1—C2—H2 | 120.2 | N5—C25—C26 | 112.7 (4) |
C2—C3—C4 | 120.1 (4) | N5—C25—C27 | 122.5 (4) |
C2—C3—H3 | 120.0 | C26—C25—C27 | 124.7 (4) |
C4—C3—H3 | 120.0 | N6—C26—C25 | 113.7 (3) |
C3—C4—C12 | 117.3 (4) | N6—C26—C28 | 125.3 (4) |
C3—C4—C5 | 125.5 (4) | C25—C26—C28 | 121.0 (4) |
C12—C4—C5 | 117.2 (4) | C25—C27—H27A | 109.5 |
C6—C5—C4 | 122.0 (4) | C25—C27—H27B | 109.5 |
C6—C5—H5 | 119.0 | H27A—C27—H27B | 109.5 |
C4—C5—H5 | 119.0 | C25—C27—H27C | 109.5 |
C5—C6—C7 | 121.2 (4) | H27A—C27—H27C | 109.5 |
C5—C6—H6 | 119.4 | H27B—C27—H27C | 109.5 |
C7—C6—H6 | 119.4 | C26—C28—H28A | 109.5 |
C8—C7—C11 | 117.2 (4) | C26—C28—H28B | 109.5 |
C8—C7—C6 | 125.3 (4) | H28A—C28—H28B | 109.5 |
C11—C7—C6 | 117.6 (5) | C26—C28—H28C | 109.5 |
C9—C8—C7 | 120.7 (4) | H28A—C28—H28C | 109.5 |
C9—C8—H8 | 119.6 | H28B—C28—H28C | 109.5 |
C7—C8—H8 | 119.6 | H3A—O3—H3B | 122 (3) |
C8—C9—C10 | 118.7 (4) | H4B—O4—H4A | 102 (8) |
C8—C9—H9 | 120.6 | H4A—O4—H4B | 102 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C27—H27A···O2 | 0.96 | 2.40 | 2.806 (5) | 105 |
C27—H27B···O8 | 0.96 | 2.50 | 3.225 (10) | 132 |
C28—H28C···O1 | 0.96 | 2.41 | 2.769 (5) | 102 |
O1—H1A···N2 | 0.82 | 2.84 | 3.006 (4) | 94 |
C1—H1···N5 | 0.93 | 2.49 | 2.972 (5) | 112 |
C13—H13···N1 | 0.93 | 2.57 | 3.027 (5) | 111 |
C22—H22···N6 | 0.93 | 2.57 | 3.033 (5) | 111 |
O1—H1A···O5i | 0.82 | 2.39 | 2.999 (4) | 131 |
O1—H1A···O6i | 0.82 | 1.90 | 2.704 (4) | 167 |
C3—H3···O5ii | 0.93 | 2.51 | 3.354 (5) | 152 |
C5—H5···O1iii | 0.93 | 2.52 | 3.331 (5) | 145 |
C18—H18···O2iv | 0.93 | 2.38 | 3.233 (5) | 152 |
C22—H22···O6v | 0.93 | 2.53 | 3.279 (5) | 137 |
C15—H15···O5vi | 0.93 | 2.54 | 3.357 (6) | 147 |
C27—H27C···O7v | 0.96 | 2.59 | 3.356 (6) | 137 |
C28—H28A···O7v | 0.96 | 2.63 | 3.316 (6) | 128 |
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1; (vi) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C12H8N2)2(C4H8N2O2)](NO3)2·2H2O |
Mr | 700.13 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 13.8102 (12), 11.9816 (11), 18.4018 (14) |
β (°) | 96.204 (2) |
V (Å3) | 3027.1 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.79 |
Crystal size (mm) | 0.31 × 0.22 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.794, 0.867 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20447, 6368, 3102 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.143, 1.01 |
No. of reflections | 6368 |
No. of parameters | 444 |
No. of restraints | 13 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.58, −0.53 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
Cu1—N1 | 1.919 (3) | Cu1—N4 | 1.937 (3) |
Cu1—N2 | 1.992 (3) | Cu1—N5 | 1.899 (3) |
Cu1—N3 | 1.950 (3) | Cu1—N6 | 1.885 (3) |
N1—Cu1—N2 | 84.03 (14) | N2—Cu1—N6 | 95.58 (13) |
N1—Cu1—N3 | 92.68 (13) | N3—Cu1—N4 | 83.61 (13) |
N1—Cu1—N4 | 175.34 (13) | N3—Cu1—N5 | 93.78 (14) |
N1—Cu1—N5 | 92.83 (13) | N3—Cu1—N6 | 174.62 (13) |
N1—Cu1—N6 | 90.22 (12) | N4—Cu1—N5 | 90.22 (12) |
N2—Cu1—N3 | 89.24 (12) | N4—Cu1—N6 | 93.71 (12) |
N2—Cu1—N4 | 93.09 (13) | N5—Cu1—N6 | 81.54 (14) |
N2—Cu1—N5 | 175.75 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C27—H27A···O2 | 0.96 | 2.40 | 2.806 (5) | 105 |
C27—H27B···O8 | 0.96 | 2.50 | 3.225 (10) | 132 |
C28—H28C···O1 | 0.96 | 2.41 | 2.769 (5) | 102 |
O1—H1A···N2 | 0.82 | 2.84 | 3.006 (4) | 94 |
C1—H1···N5 | 0.93 | 2.49 | 2.972 (5) | 112 |
C13—H13···N1 | 0.93 | 2.57 | 3.027 (5) | 111 |
C22—H22···N6 | 0.93 | 2.57 | 3.033 (5) | 111 |
O1—H1A···O5i | 0.82 | 2.39 | 2.999 (4) | 131 |
O1—H1A···O6i | 0.82 | 1.90 | 2.704 (4) | 167 |
C3—H3···O5ii | 0.93 | 2.51 | 3.354 (5) | 152 |
C5—H5···O1iii | 0.93 | 2.52 | 3.331 (5) | 145 |
C18—H18···O2iv | 0.93 | 2.38 | 3.233 (5) | 152 |
C22—H22···O6v | 0.93 | 2.53 | 3.279 (5) | 137 |
C15—H15···O5vi | 0.93 | 2.54 | 3.357 (6) | 147 |
C27—H27C···O7v | 0.96 | 2.59 | 3.356 (6) | 137 |
C28—H28A···O7v | 0.96 | 2.63 | 3.316 (6) | 128 |
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1; (vi) x, y, z−1. |
The crystal structure of (dimethylglyoxime-κ2N,N')bis(1,10-phenanthroline- κ2N,N')nickel(II)dinitrate dihydrate, (II), (Zhong et al., 2007a) and (dimethylglyoxime-κ2N,N')bis(1,10-phenanthroline-κ2N,N')zinc(II)dinitrate dihydrate, (III), (Zhong et al., 2007b) have previously been reported. The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with those of (II) and (III). We report herein the crystal structure of (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six N atoms from one dimethylglyoxime and two 1,10-phenanthroline (phen) ligands are coordinated to the Cu atom in a distorted octahedral arrangement (Table 1). The dimethylglyoxime and two phen ligands are each planar, and the phen ligands are nearly perpendicular to each other, the dihedral angle of 86.04 (3)° being the same as in (II) and (III).
In the crystal structure, the molecules are linked into a three-dimensional framework by O—H···O and C—H···O hydrogen bonds (Table 2). There are π-π stacking interactions between adjacent phen ligands with a centroid-centroid distance of 3.592 (4) Å (symmetry code: 1 - x, 2 - y, 1 - z); this compares with 3.602 (3) and 3.5997 (7) Å in (II) and (III), respectively. These π-π stacking interactions and hydrogen bonds (Table 2) lead to a supramolecular network structure (Fig. 2), as in (II) and (III).
Compounds (I), (II) and (III) are isostructural.