Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010750/ng2016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010750/ng2016Isup2.hkl |
CCDC reference: 605134
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.006 Å
- H-atom completeness 86%
- Disorder in main residue
- R factor = 0.031
- wR factor = 0.079
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
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)... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.84 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.844(10) ...... 4.00 su-Rat O3 -H31 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.848(10) ...... 4.00 su-Rat O3 -H32 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.844(10) ...... 4.00 su-Rat O4 -H41 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.844(10) ...... 4.00 su-Rat O3 -H31 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.848(10) ...... 4.00 su-Rat O3 -H32 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.844(10) ...... 4.00 su-Rat O4 -H41 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.844(10) ...... 4.00 su-Rat O4 -H41 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.97(5), Rep 1.98(2) ...... 2.50 su-Rat H32 -O4 1.555 7.667
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:C4 H7 Cl1 Cu1 O7 Atom count from the _atom_site data: C4 H6 Cl1 Cu1 O7 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 4 From the CIF: _chemical_formula_sum C4 H7 Cl Cu O7 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 16.00 16.00 0.00 H 28.00 24.00 4.00 Cl 4.00 4.00 0.00 Cu 4.00 4.00 0.00 O 28.00 28.00 0.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 14 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXL97.
[Cu(C4HClO4)(H2O)2]·H2O | F(000) = 532 |
Mr = 266.09 | Dx = 2.087 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2y | Cell parameters from 6215 reflections |
a = 14.849 (3) Å | θ = 1.5–32.4° |
b = 7.1407 (6) Å | µ = 2.90 mm−1 |
c = 8.7237 (15) Å | T = 170 K |
β = 113.751 (13)° | Plate, blue |
V = 846.7 (2) Å3 | 0.2 × 0.2 × 0.05 mm |
Z = 4 |
Stoe IPDS-II diffractometer | 1109 independent reflections |
Radiation source: fine-focus sealed tube | 1019 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: not measured pixels mm-1 | θmax = 28.0°, θmin = 2.6° |
ω and φ scans | h = −19→19 |
Absorption correction: numerical The absorption correction (X-RED; Stoe & Cie, 2001) was performed after optimizing the crystal shape using X-SHAPE (Stoe & Cie, 1999). | k = −9→8 |
Tmin = 0.531, Tmax = 0.847 | l = −11→11 |
7365 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.0435P)2 + 2.1723P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
1109 reflections | Δρmax = 0.74 e Å−3 |
92 parameters | Δρmin = −0.66 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0054 (11) |
Experimental. A suitable single-crystal was carefully selected under a polarizing microscope and mounted in a glass capillary. The scattering intensities were collected on an imaging plate diffractometer (IPDS II, Stoe & Cie) equipped with a fine focus sealed tube X-ray source (Mo Kα, λ = 0.71073 Å) operating at 50 kV and 40 mA. Intensity data for the title compound were collected at 170 K by ω-scans in 180 frames (0 < ω < 180°; φ = O°, 0 < ω < 180°; φ = 90°, Δω = 2°, exposure time of 4 min) in the 2 Θ range 2.9 to 64.8°. Structure solution and refinement were carried out using the programs SIR92 (Altomare et al., 1993) and SHELXL97 (Sheldrick, 1997). The methylene H atom was placed in idealized position and constrained to ride on their parent atom, with C—H distances of 0.930 Å and Uiso(H) values of 0.042 Å2. The remaining H atoms were located in a difference Fourier map and refined, with O—H2 distances restrained to 0.82 (2) Å. A numerical absorption correction (X-RED (Stoe & Cie, 2001b) was applied after optimization of the crystal shape (X-SHAPE (Stoe & Cie, 1999)). The last cycles of refinement included atomic positions for all atoms, anisotropic parameters for all non-hydrogen atoms and isotropic thermal parameters for all hydrogen atoms. The final difference maps were free of any chemically significant features. The refinement was based on F2 for ALL reflections. |
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 | Occ. (<1) | |
Cu1 | 0.91085 (3) | 0.5000 | 1.06457 (5) | 0.01759 (16) | |
C1 | 0.8398 (3) | 0.5000 | 0.7198 (5) | 0.0448 (12) | |
O11 | 0.92114 (18) | 0.5000 | 0.8482 (3) | 0.0251 (5) | |
O12 | 0.7617 (3) | 0.5506 (8) | 0.7315 (5) | 0.046 (2) | 0.50 |
C2 | 0.8529 (3) | 0.5000 | 0.5582 (5) | 0.0451 (13) | |
H2 | 0.9174 | 0.5000 | 0.5672 | 0.043 (15)* | |
C3 | 0.7835 (3) | 0.5000 | 0.4043 (5) | 0.0390 (11) | |
Cl1 | 0.65892 (7) | 0.5000 | 0.35671 (12) | 0.0496 (4) | |
C4 | 0.8088 (3) | 0.5000 | 0.2530 (5) | 0.0341 (9) | |
O41 | 0.8999 (2) | 0.5000 | 0.2814 (3) | 0.0330 (7) | |
O42 | 0.7420 (2) | 0.5000 | 0.1107 (4) | 0.0445 (9) | |
O3 | 0.91202 (18) | 0.7759 (3) | 1.0631 (3) | 0.0416 (6) | |
H31 | 0.863 (2) | 0.825 (7) | 0.986 (4) | 0.072 (15)* | |
H32 | 0.913 (5) | 0.822 (8) | 1.154 (4) | 0.10 (2)* | |
O4 | 0.5695 (2) | 0.5000 | 0.6635 (4) | 0.0307 (6) | |
H41 | 0.624 (2) | 0.5000 | 0.655 (8) | 0.062 (19)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0169 (2) | 0.0227 (2) | 0.0134 (2) | 0.000 | 0.00624 (15) | 0.000 |
C1 | 0.0227 (19) | 0.095 (4) | 0.0162 (16) | 0.000 | 0.0078 (14) | 0.000 |
O11 | 0.0200 (12) | 0.0402 (14) | 0.0148 (11) | 0.000 | 0.0066 (9) | 0.000 |
O12 | 0.0176 (15) | 0.099 (7) | 0.0190 (14) | 0.002 (2) | 0.0039 (12) | 0.000 (2) |
C2 | 0.0159 (17) | 0.098 (4) | 0.0204 (18) | 0.000 | 0.0066 (14) | 0.000 |
C3 | 0.0189 (18) | 0.079 (3) | 0.0193 (17) | 0.000 | 0.0080 (14) | 0.000 |
Cl1 | 0.0149 (4) | 0.1080 (11) | 0.0247 (5) | 0.000 | 0.0070 (3) | 0.000 |
C4 | 0.0227 (17) | 0.063 (3) | 0.0196 (16) | 0.000 | 0.0114 (14) | 0.000 |
O41 | 0.0195 (12) | 0.063 (2) | 0.0159 (11) | 0.000 | 0.0063 (10) | 0.000 |
O42 | 0.0208 (13) | 0.091 (3) | 0.0201 (13) | 0.000 | 0.0062 (11) | 0.000 |
O3 | 0.0557 (14) | 0.0240 (9) | 0.0261 (10) | 0.0057 (9) | −0.0034 (10) | −0.0028 (8) |
O4 | 0.0248 (13) | 0.0386 (15) | 0.0298 (14) | 0.000 | 0.0121 (11) | 0.000 |
Cu1—O11 | 1.954 (2) | C2—C3 | 1.322 (6) |
Cu1—O41i | 1.962 (3) | C2—H2 | 0.9300 |
Cu1—O3ii | 1.970 (2) | C3—C4 | 1.511 (5) |
Cu1—O3 | 1.970 (2) | C3—Cl1 | 1.726 (4) |
Cu1—O11iii | 2.297 (3) | C4—O42 | 1.239 (5) |
C1—O12ii | 1.257 (6) | C4—O41 | 1.273 (5) |
C1—O12 | 1.257 (6) | O41—Cu1iv | 1.962 (3) |
C1—O11 | 1.274 (5) | O3—H31 | 0.844 (10) |
C1—C2 | 1.498 (5) | O3—H32 | 0.848 (10) |
O11—Cu1iii | 2.297 (3) | O4—H41 | 0.844 (10) |
O12—O12ii | 0.722 (12) | ||
O11—Cu1—O41i | 179.76 (11) | C1—O11—Cu1iii | 144.1 (2) |
O11—Cu1—O3ii | 89.41 (7) | Cu1—O11—Cu1iii | 100.21 (10) |
O41i—Cu1—O3ii | 90.60 (7) | O12ii—O12—C1 | 73.3 (3) |
O11—Cu1—O3 | 89.41 (7) | C3—C2—C1 | 127.8 (4) |
O41i—Cu1—O3 | 90.60 (7) | C3—C2—H2 | 116.1 |
O3ii—Cu1—O3 | 178.54 (16) | C1—C2—H2 | 116.1 |
O11—Cu1—O11iii | 79.79 (10) | C2—C3—C4 | 121.4 (4) |
O41i—Cu1—O11iii | 100.44 (10) | C2—C3—Cl1 | 124.4 (3) |
O3ii—Cu1—O11iii | 89.48 (8) | C4—C3—Cl1 | 114.2 (3) |
O3—Cu1—O11iii | 89.48 (8) | O42—C4—O41 | 123.6 (3) |
O12ii—C1—O11 | 120.5 (4) | O42—C4—C3 | 119.7 (4) |
O12—C1—O11 | 120.5 (4) | O41—C4—C3 | 116.7 (3) |
O12ii—C1—C2 | 123.3 (4) | C4—O41—Cu1iv | 107.8 (2) |
O12—C1—C2 | 123.3 (4) | Cu1—O3—H31 | 115 (4) |
O11—C1—C2 | 113.1 (3) | Cu1—O3—H32 | 112 (4) |
C1—O11—Cu1 | 115.7 (2) | H31—O3—H32 | 106 (5) |
O12ii—C1—O11—Cu1 | −19.5 (3) | C2—C1—O12—O12ii | 101.4 (2) |
O12—C1—O11—Cu1 | 19.5 (3) | O12ii—C1—C2—C3 | 20.1 (3) |
C2—C1—O11—Cu1 | 180.0 | O12—C1—C2—C3 | −20.1 (3) |
O12ii—C1—O11—Cu1iii | 160.5 (3) | O11—C1—C2—C3 | 180.000 (1) |
O12—C1—O11—Cu1iii | −160.5 (3) | C1—C2—C3—C4 | 180.0 |
C2—C1—O11—Cu1iii | 0.0 | C1—C2—C3—Cl1 | 0.000 (1) |
O3ii—Cu1—O11—C1 | 90.42 (7) | C2—C3—C4—O42 | 180.0 |
O3—Cu1—O11—C1 | −90.42 (7) | Cl1—C3—C4—O42 | 0.0 |
O11iii—Cu1—O11—C1 | 180.000 (1) | C2—C3—C4—O41 | 0.0 |
O3ii—Cu1—O11—Cu1iii | −89.58 (7) | Cl1—C3—C4—O41 | 180.0 |
O3—Cu1—O11—Cu1iii | 89.58 (7) | O42—C4—O41—Cu1iv | 0.0 |
O11iii—Cu1—O11—Cu1iii | 0.0 | C3—C4—O41—Cu1iv | 180.0 |
O11—C1—O12—O12ii | −100.2 (2) |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+1, z; (iii) −x+2, −y+1, −z+2; (iv) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H31···O42v | 0.84 (1) | 1.91 (2) | 2.702 (3) | 156 (5) |
O3—H32···O4vi | 0.85 (1) | 1.98 (2) | 2.792 (3) | 161 (6) |
O4—H41···O12 | 0.84 (1) | 1.91 (3) | 2.696 (5) | 154 (6) |
O4—H41···O12ii | 0.84 (1) | 1.91 (3) | 2.696 (5) | 154 (6) |
Symmetry codes: (ii) x, −y+1, z; (v) −x+3/2, −y+3/2, −z+1; (vi) −x+3/2, −y+3/2, −z+2. |
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