Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054244/hg2336sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054244/hg2336Isup2.hkl |
CCDC reference: 1176497
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.027
- wR factor = 0.076
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O6 .. 5.23 su PLAT417_ALERT_2_C Short Inter D-H..H-D H9 .. H10D .. 2.10 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.31 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
A mixture of dimethylglyoxime (0.116 g, 0.001 mol), 2-hydroxy-3,5-dinitrobenzoic acid (0.228 g, 0.001 mol) and CuSO4.5H2O (0.250 g, 0.001 mol) in the mole ratio of 1:1:1 was added to 15 ml me thanol, The mixture was heated at 408 K for two days in a closed steel chamber with liner. Crystals of (I) were obtained after reaction mixture cooled to room temperature, untouched in the air.
The H atoms bonding to C atoms and O atoms of hydroxyl group were located at calculated positions and refined as riding on their parent atoms with the bond length fixed to 0.93 Å for C—H and 0.82 Å for O—H, Uiso(H) being 1.2 times Ueq(C) and Uiso(H) being 1.5 times Ueq(O); The H atoms bonding to O atoms of water molecules are found in electron density map and refined with bond lengths fixed to 0.82 Å and with Uiso(H) = 1.5 times Ueq(O).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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(C7H2N2O7)(C4H8N2O2)(H2O)] | F(000) = 860.0 |
Mr = 423.80 | Dx = 1.825 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7646 reflections |
a = 12.476 (2) Å | θ = 1.0–28.3° |
b = 7.0786 (14) Å | µ = 1.48 mm−1 |
c = 17.929 (4) Å | T = 293 K |
β = 103.014 (3)° | Block, green |
V = 1542.7 (5) Å3 | 0.30 × 0.28 × 0.23 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2426 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 25.5°, θmin = 2.3° |
ϕ and ω scans | h = −14→15 |
9276 measured reflections | k = −8→8 |
2824 independent reflections | l = −21→21 |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0413P)2 + 0.7936P] where P = (Fo2 + 2Fc2)/3 |
2824 reflections | (Δ/σ)max = 0.009 |
245 parameters | Δρmax = 0.24 e Å−3 |
2 restraints | Δρmin = −0.37 e Å−3 |
[Cu(C7H2N2O7)(C4H8N2O2)(H2O)] | V = 1542.7 (5) Å3 |
Mr = 423.80 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.476 (2) Å | µ = 1.48 mm−1 |
b = 7.0786 (14) Å | T = 293 K |
c = 17.929 (4) Å | 0.30 × 0.28 × 0.23 mm |
β = 103.014 (3)° |
Bruker SMART CCD area-detector diffractometer | 2426 reflections with I > 2σ(I) |
9276 measured reflections | Rint = 0.019 |
2824 independent reflections |
R[F2 > 2σ(F2)] = 0.028 | 2 restraints |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.24 e Å−3 |
2824 reflections | Δρmin = −0.37 e Å−3 |
245 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 | ||
C1 | 0.38551 (19) | 0.8248 (3) | −0.15661 (11) | 0.0404 (5) | |
C2 | 0.29055 (18) | 0.8483 (3) | −0.12966 (12) | 0.0401 (5) | |
H2 | 0.2493 | 0.9582 | −0.1412 | 0.048* | |
C3 | 0.25689 (17) | 0.7102 (3) | −0.08585 (12) | 0.0363 (4) | |
C4 | 0.31727 (17) | 0.5362 (3) | −0.07025 (11) | 0.0350 (4) | |
C5 | 0.41421 (17) | 0.5223 (3) | −0.09927 (11) | 0.0353 (4) | |
C6 | 0.44863 (18) | 0.6661 (3) | −0.14088 (11) | 0.0384 (5) | |
H6 | 0.5136 | 0.6546 | −0.1578 | 0.046* | |
C7 | 0.15805 (18) | 0.7568 (3) | −0.05472 (13) | 0.0411 (5) | |
C8 | 0.2461 (2) | −0.0793 (4) | 0.17133 (16) | 0.0591 (7) | |
H8A | 0.2924 | −0.1435 | 0.1434 | 0.089* | |
H8B | 0.1793 | −0.1496 | 0.1677 | 0.089* | |
H8C | 0.2838 | −0.0685 | 0.2241 | 0.089* | |
C9 | 0.21941 (18) | 0.1124 (3) | 0.13856 (13) | 0.0410 (5) | |
C10 | 0.1053 (2) | 0.2011 (4) | 0.23823 (15) | 0.0652 (7) | |
H10A | 0.0880 | 0.3172 | 0.2606 | 0.098* | |
H10B | 0.1617 | 0.1356 | 0.2742 | 0.098* | |
H10C | 0.0407 | 0.1236 | 0.2254 | 0.098* | |
C11 | 0.14519 (18) | 0.2433 (3) | 0.16737 (13) | 0.0433 (5) | |
Cu1 | 0.19075 (2) | 0.41715 (4) | 0.035805 (15) | 0.04118 (11) | |
H10D | −0.0046 (14) | 0.236 (4) | −0.0242 (14) | 0.062* | |
N1 | 0.41829 (19) | 0.9717 (3) | −0.20416 (11) | 0.0530 (5) | |
N2 | 0.48523 (15) | 0.3558 (3) | −0.08565 (10) | 0.0426 (4) | |
N3 | 0.25563 (15) | 0.1820 (3) | 0.08278 (10) | 0.0407 (4) | |
N4 | 0.11864 (16) | 0.3920 (3) | 0.12651 (11) | 0.0427 (4) | |
O1 | 0.50885 (18) | 0.9593 (3) | −0.21873 (12) | 0.0732 (6) | |
O2 | 0.35331 (19) | 1.0994 (3) | −0.22715 (13) | 0.0824 (7) | |
O3 | 0.57503 (15) | 0.3662 (3) | −0.10244 (12) | 0.0686 (5) | |
O4 | 0.45639 (15) | 0.2139 (2) | −0.05650 (11) | 0.0628 (5) | |
O5 | 0.10172 (14) | 0.8950 (2) | −0.08023 (11) | 0.0537 (4) | |
O6 | 0.13474 (13) | 0.6566 (2) | −0.00051 (10) | 0.0496 (4) | |
O7 | 0.28662 (14) | 0.3991 (2) | −0.03241 (10) | 0.0486 (4) | |
O8 | 0.32359 (15) | 0.0709 (2) | 0.05102 (10) | 0.0514 (4) | |
H8 | 0.3401 | 0.1273 | 0.0152 | 0.077* | |
O9 | 0.05087 (16) | 0.5146 (3) | 0.15476 (10) | 0.0601 (5) | |
H9 | 0.0242 | 0.5917 | 0.1216 | 0.090* | |
O10 | 0.04730 (13) | 0.2463 (2) | −0.04495 (10) | 0.0461 (4) | |
H10E | 0.067 (2) | 0.1386 (16) | −0.0517 (17) | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0492 (13) | 0.0408 (12) | 0.0330 (10) | −0.0073 (10) | 0.0130 (9) | 0.0008 (9) |
C2 | 0.0439 (13) | 0.0342 (11) | 0.0425 (11) | 0.0011 (9) | 0.0102 (10) | 0.0015 (9) |
C3 | 0.0377 (11) | 0.0316 (10) | 0.0413 (11) | 0.0015 (8) | 0.0127 (9) | −0.0009 (8) |
C4 | 0.0385 (12) | 0.0318 (10) | 0.0371 (10) | 0.0007 (8) | 0.0132 (9) | −0.0024 (8) |
C5 | 0.0369 (11) | 0.0362 (11) | 0.0336 (10) | 0.0015 (9) | 0.0099 (9) | −0.0050 (8) |
C6 | 0.0385 (12) | 0.0461 (12) | 0.0337 (10) | −0.0043 (9) | 0.0146 (9) | −0.0061 (9) |
C7 | 0.0422 (12) | 0.0291 (10) | 0.0549 (13) | 0.0027 (9) | 0.0173 (10) | −0.0021 (9) |
C8 | 0.0606 (17) | 0.0538 (16) | 0.0655 (16) | 0.0111 (12) | 0.0195 (13) | 0.0209 (12) |
C9 | 0.0358 (12) | 0.0430 (12) | 0.0433 (12) | 0.0000 (9) | 0.0072 (9) | 0.0055 (9) |
C10 | 0.0740 (19) | 0.0716 (19) | 0.0599 (16) | 0.0073 (15) | 0.0355 (14) | 0.0187 (14) |
C11 | 0.0404 (12) | 0.0474 (13) | 0.0449 (12) | 0.0006 (10) | 0.0157 (10) | 0.0055 (10) |
Cu1 | 0.04485 (19) | 0.03550 (16) | 0.04994 (18) | 0.00842 (11) | 0.02486 (13) | 0.00724 (11) |
N1 | 0.0602 (14) | 0.0563 (13) | 0.0437 (11) | −0.0084 (11) | 0.0142 (10) | 0.0097 (10) |
N2 | 0.0414 (11) | 0.0446 (10) | 0.0451 (10) | 0.0068 (8) | 0.0167 (8) | −0.0052 (8) |
N3 | 0.0374 (10) | 0.0410 (10) | 0.0463 (10) | 0.0078 (8) | 0.0144 (8) | 0.0034 (8) |
N4 | 0.0437 (11) | 0.0441 (11) | 0.0459 (10) | 0.0050 (8) | 0.0217 (8) | 0.0015 (8) |
O1 | 0.0728 (13) | 0.0851 (15) | 0.0731 (13) | −0.0076 (11) | 0.0406 (11) | 0.0216 (11) |
O2 | 0.0788 (15) | 0.0783 (15) | 0.0921 (15) | 0.0053 (12) | 0.0232 (12) | 0.0472 (12) |
O3 | 0.0457 (11) | 0.0734 (13) | 0.0959 (15) | 0.0171 (9) | 0.0354 (10) | 0.0108 (11) |
O4 | 0.0661 (12) | 0.0438 (10) | 0.0892 (13) | 0.0153 (9) | 0.0395 (10) | 0.0101 (9) |
O5 | 0.0490 (10) | 0.0368 (9) | 0.0795 (12) | 0.0138 (7) | 0.0231 (9) | 0.0081 (8) |
O6 | 0.0509 (10) | 0.0398 (8) | 0.0691 (10) | 0.0115 (7) | 0.0363 (8) | 0.0090 (8) |
O7 | 0.0551 (10) | 0.0344 (8) | 0.0677 (11) | 0.0114 (7) | 0.0378 (9) | 0.0112 (7) |
O8 | 0.0528 (10) | 0.0488 (10) | 0.0588 (10) | 0.0178 (8) | 0.0256 (8) | 0.0069 (7) |
O9 | 0.0734 (13) | 0.0563 (11) | 0.0623 (11) | 0.0224 (9) | 0.0396 (10) | 0.0081 (9) |
O10 | 0.0425 (9) | 0.0378 (8) | 0.0638 (10) | 0.0084 (7) | 0.0239 (8) | 0.0006 (8) |
C1—C6 | 1.364 (3) | C10—C11 | 1.495 (3) |
C1—C2 | 1.387 (3) | C10—H10A | 0.9600 |
C1—N1 | 1.461 (3) | C10—H10B | 0.9600 |
C2—C3 | 1.378 (3) | C10—H10C | 0.9600 |
C2—H2 | 0.9300 | C11—N4 | 1.282 (3) |
C3—C4 | 1.438 (3) | Cu1—O6 | 1.8922 (16) |
C3—C7 | 1.500 (3) | Cu1—O7 | 1.8978 (16) |
C4—O7 | 1.290 (3) | Cu1—N3 | 1.9566 (18) |
C4—C5 | 1.424 (3) | Cu1—N4 | 2.0359 (19) |
C5—C6 | 1.386 (3) | Cu1—O10 | 2.3652 (18) |
C5—N2 | 1.461 (3) | N1—O1 | 1.219 (3) |
C6—H6 | 0.9300 | N1—O2 | 1.222 (3) |
C7—O5 | 1.231 (3) | N2—O4 | 1.223 (3) |
C7—O6 | 1.288 (3) | N2—O3 | 1.226 (3) |
C8—C9 | 1.486 (3) | N3—O8 | 1.370 (2) |
C8—H8A | 0.9600 | N4—O9 | 1.385 (2) |
C8—H8B | 0.9600 | O8—H8 | 0.8200 |
C8—H8C | 0.9600 | O9—H9 | 0.8200 |
C9—N3 | 1.285 (3) | O10—H10D | 0.82 (2) |
C9—C11 | 1.483 (3) | O10—H10E | 0.818 (14) |
C6—C1—C2 | 121.7 (2) | H10A—C10—H10C | 109.5 |
C6—C1—N1 | 118.9 (2) | H10B—C10—H10C | 109.5 |
C2—C1—N1 | 119.4 (2) | N4—C11—C9 | 114.51 (19) |
C1—C2—C3 | 120.5 (2) | N4—C11—C10 | 123.9 (2) |
C1—C2—H2 | 119.8 | C9—C11—C10 | 121.6 (2) |
C3—C2—H2 | 119.8 | O6—Cu1—O7 | 94.35 (6) |
C2—C3—C4 | 120.4 (2) | O6—Cu1—N3 | 174.35 (8) |
C2—C3—C7 | 115.96 (19) | O7—Cu1—N3 | 87.74 (7) |
C4—C3—C7 | 123.67 (18) | O6—Cu1—N4 | 99.09 (7) |
O7—C4—C5 | 121.14 (19) | O7—Cu1—N4 | 164.78 (7) |
O7—C4—C3 | 122.82 (19) | N3—Cu1—N4 | 78.23 (7) |
C5—C4—C3 | 116.04 (19) | O6—Cu1—O10 | 94.44 (7) |
C6—C5—C4 | 122.52 (19) | O7—Cu1—O10 | 94.07 (7) |
C6—C5—N2 | 115.62 (19) | N3—Cu1—O10 | 90.64 (7) |
C4—C5—N2 | 121.85 (19) | N4—Cu1—O10 | 91.98 (7) |
C1—C6—C5 | 118.8 (2) | O1—N1—O2 | 123.9 (2) |
C1—C6—H6 | 120.6 | O1—N1—C1 | 117.9 (2) |
C5—C6—H6 | 120.6 | O2—N1—C1 | 118.2 (2) |
O5—C7—O6 | 120.7 (2) | O4—N2—O3 | 121.8 (2) |
O5—C7—C3 | 119.0 (2) | O4—N2—C5 | 120.52 (18) |
O6—C7—C3 | 120.26 (19) | O3—N2—C5 | 117.6 (2) |
C9—C8—H8A | 109.5 | C9—N3—O8 | 117.55 (18) |
C9—C8—H8B | 109.5 | C9—N3—Cu1 | 118.50 (15) |
H8A—C8—H8B | 109.5 | O8—N3—Cu1 | 122.95 (13) |
C9—C8—H8C | 109.5 | C11—N4—O9 | 113.93 (18) |
H8A—C8—H8C | 109.5 | C11—N4—Cu1 | 115.12 (15) |
H8B—C8—H8C | 109.5 | O9—N4—Cu1 | 130.79 (14) |
N3—C9—C11 | 112.86 (19) | C7—O6—Cu1 | 128.62 (14) |
N3—C9—C8 | 124.8 (2) | C4—O7—Cu1 | 126.36 (13) |
C11—C9—C8 | 122.3 (2) | N3—O8—H8 | 109.5 |
C11—C10—H10A | 109.5 | N4—O9—H9 | 109.5 |
C11—C10—H10B | 109.5 | Cu1—O10—H10D | 109.4 (19) |
H10A—C10—H10B | 109.5 | Cu1—O10—H10E | 111 (2) |
C11—C10—H10C | 109.5 | H10D—O10—H10E | 106 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9···O10i | 0.82 | 1.86 | 2.675 (2) | 175 |
O8—H8···O7 | 0.82 | 2.15 | 2.745 (2) | 130 |
O8—H8···O4 | 0.82 | 2.23 | 2.987 (2) | 154 |
O10—H10E···O5ii | 0.82 (1) | 1.88 (2) | 2.691 (2) | 173 (3) |
O10—H10D···O6i | 0.82 (2) | 1.93 (1) | 2.670 (2) | 149 (3) |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C7H2N2O7)(C4H8N2O2)(H2O)] |
Mr | 423.80 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.476 (2), 7.0786 (14), 17.929 (4) |
β (°) | 103.014 (3) |
V (Å3) | 1542.7 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.48 |
Crystal size (mm) | 0.30 × 0.28 × 0.23 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9276, 2824, 2426 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.605 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.076, 1.01 |
No. of reflections | 2824 |
No. of parameters | 245 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.37 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9···O10i | 0.82 | 1.86 | 2.675 (2) | 174.9 |
O8—H8···O7 | 0.82 | 2.15 | 2.745 (2) | 129.5 |
O8—H8···O4 | 0.82 | 2.23 | 2.987 (2) | 153.5 |
O10—H10E···O5ii | 0.818 (14) | 1.877 (15) | 2.691 (2) | 173 (3) |
O10—H10D···O6i | 0.82 (2) | 1.932 (14) | 2.670 (2) | 149 (3) |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z. |
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As shown in Fig. 1, (I) crystallizes as discrete molecular species. Each copper(II) ion is five-coordinated in a distorted pyramidal geometry by two N atoms from one dimethylglyoxime molecule, two O atoms from one 2-hydroxy-3,5-dinitrobenzoic acid molecule and one O atom from a water molecule. Atoms O6, O7, N3 and N4 located at the base of the pyramid are approximately coplanar with the central Cu1 ion, the maximum deviation from the least-squares plane through all five atoms being 0.081 Å for Cu1, O10 locating at the apex of the pyramid shows a slightly longer bond to Cu1 than O7 and O8. Strong hydrogen bonds are found between adjacent molecules, which including: O(9)—H(9)···O(10)1 (symmetry code 1: -x,-y + 1,-z); O(10)—H(10E)···O(5)2 (symmetry code 2:x,y - 1,z) and O(10)—H(10D)···O(6)1.