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The title compound, [Cu(C5H8NO2)(C9H10NO2)(H2O)]·H2O, is formed by the chelate coordination of L-prolinate and L-phenyl­alaninate anions. Both ligands bind through carboxyl­ate O and amine N atoms to the CuII atom in a trans arrangement. The square pyramid is completed by an aqua ligand in the apical position.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048513/ob2097sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048513/ob2097Isup2.hkl
Contains datablock I

CCDC reference: 630202

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.010 Å
  • H-atom completeness 91%
  • R factor = 0.057
  • wR factor = 0.168
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O6
Author Response: Hydrogen atoms from crystallization water molecule were not found in \DF maps and were disregarded in the final model (see text).

Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.03 Ratio PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O6 .. 2.78 Ang.
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)... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
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:C14 H22 Cu1 N2 O6 Atom count from the _atom_site data: C14 H20 Cu1 N2 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 4 From the CIF: _chemical_formula_sum C14 H22 Cu N2 O6 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 56.00 56.00 0.00 H 88.00 80.00 8.00 Cu 4.00 4.00 0.00 N 8.00 8.00 0.00 O 24.00 24.00 0.00 REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.52 From the CIF: _reflns_number_total 2415 Count of symmetry unique reflns 2182 Completeness (_total/calc) 110.68% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 233 Fraction of Friedel pairs measured 0.107 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of N1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 9 ALERT level G = General alerts; check 10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: MSC/AFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: PLATON (Spek, 2003).

Aqua(L-phenylalaninato)(L-prolinato)copper(II) monohydrate top
Crystal data top
[Cu(C5H8NO2)(C9H10NO2)(H2O)]·H2OF(000) = 788
Mr = 377.88Dx = 1.544 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 12.663 (3) Åθ = 5.1–11.6°
b = 22.894 (3) ŵ = 1.38 mm1
c = 5.609 (3) ÅT = 293 K
V = 1626.1 (10) Å3Needle, blue
Z = 40.30 × 0.03 × 0.01 mm
Data collection top
Rigaku AFC-7S
diffractometer
1983 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
ω/2θ scansh = 816
Absorption correction: ψ scan
(North et al., 1968)
k = 2029
Tmin = 0.683, Tmax = 0.986l = 47
2508 measured reflections3 standard reflections every 150 reflections
2415 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.168 w = 1/[σ2(Fo2) + (0.118P)2 + 1.1436P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2415 reflectionsΔρmax = 1.08 e Å3
215 parametersΔρmin = 0.65 e Å3
20 restraintsAbsolute structure: Flack (1983), 235 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (3)
Special details top

Experimental. Elemental analyses (C,H,N) were performed on a Carlo Erba model 1108 elemental analyzer. IR spectrometry on KBr pellets was performed with a Bomem MB-102 FTIR spectrometer. The spectra show the absorption lines assigned to the aminoacid ligands 1601(s), 1387(m), 1135(m), 1089(w), 937(w), 890(w), 856(w), 828(w), 749(w), 701(m) cm-1.

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.

———————————————

Interaction among π rings:

C9—C10—C11—C12—C13—C14-

LS-Plane: 0.678 (2)*x - 0.578 (2)*y + 0.454 (3)*z=5.386 (17)

Deviations from plane #C(9) 0.010 (5) #C(10) -0.005 (7) #C(11) -0.006 (7) #C(12) 0.011 (8) #C(13) -0.006 (8) #C(14) -0.005 (7)

Ring centroid (CG) coodinates (x,y,z): (0.5929 (2),0.02425 (12),0.2417 (6))

Closes CG—CG interaction

CG—CGi 4.993 (5) Å perpendicular distance between rings 2.065 Å distance between CG and the projection of CGi in CG's plane 4.613 Å

i=[2655] = 3/2-X,-Y,1/2+Z

NOTE: THIS IS NOT CONSIDERED A ππ STACKING INTERACTION

Refinement. Conformational disorder in the five-membered ring could be invoked to explain the observed behavior together with the observed C—C bond distances between C3, C4 and C5 that are shorter than expected for C(sp3)—C(sp3) (see suplementary material). The use of optically pure L-aminoacids allowed to postulate the absolute structure of the compound, afterwards confirmed by refinement. The needle-shaped crystals obtained showed twinning and the cut piece used for data collection did not diffract adequately. Accordingly, the data set gathered was of poor quality, as evidenced in the rather large Rint factor attained (0.0451) with about 10% of redundant reflections.

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
xyzUiso*/Ueq
Cu0.47313 (5)0.18848 (3)0.16380 (12)0.0338 (2)
O10.3717 (3)0.1901 (2)0.4263 (8)0.0459 (11)
C10.2762 (5)0.1785 (3)0.3711 (10)0.0344 (12)
O20.2026 (3)0.1801 (2)0.5147 (9)0.0467 (11)
C20.2544 (5)0.1609 (3)0.1113 (11)0.0374 (14)
H20.20830.19020.03840.045*
C30.2007 (8)0.1013 (4)0.095 (2)0.077 (3)
H3A0.20030.08220.24970.115*
H3B0.12850.10530.04030.115*
C40.2648 (8)0.0672 (4)0.079 (3)0.092 (3)
H4A0.27200.02710.02660.137*
H4B0.23070.06730.23420.137*
C50.3684 (6)0.0948 (3)0.0957 (17)0.0553 (18)
H5C0.39580.09170.25670.083*
H5D0.41770.07600.01220.083*
N10.3542 (4)0.1574 (2)0.0287 (9)0.0341 (11)
H10.34740.17920.16360.041*
O30.5751 (3)0.1797 (2)0.0941 (7)0.0380 (10)
C60.6717 (5)0.1837 (3)0.0295 (10)0.0315 (11)
O40.7465 (3)0.1855 (2)0.1726 (8)0.0487 (11)
C70.6945 (4)0.1834 (3)0.2382 (10)0.0285 (11)
H70.75010.21210.27050.034*
N20.5985 (4)0.2017 (2)0.3650 (9)0.0322 (10)
H2A0.60310.23990.40240.039*
H2B0.59220.18130.50140.039*
C80.7357 (4)0.1229 (2)0.3098 (12)0.0356 (12)
H8A0.79960.11510.21990.053*
H8B0.75490.12400.47720.053*
C90.6594 (5)0.0725 (2)0.2714 (11)0.0334 (12)
C100.6666 (6)0.0390 (3)0.0682 (13)0.0433 (15)
H100.71530.04850.04960.065*
C110.5997 (6)0.0098 (3)0.0393 (14)0.0519 (18)
H110.60430.03240.09820.078*
C120.5274 (6)0.0243 (3)0.2152 (16)0.059 (2)
H120.48480.05710.19810.089*
C130.5192 (7)0.0101 (3)0.4143 (15)0.061 (2)
H130.46940.00120.53080.092*
C140.5849 (6)0.0582 (3)0.4426 (13)0.0476 (16)
H140.57870.08110.57870.071*
O50.4500 (4)0.2877 (2)0.0805 (12)0.0548 (14)
H5A0.391 (5)0.288 (4)0.09 (2)0.082*
H5B0.474 (7)0.308 (4)0.012 (18)0.082*
O60.4911 (5)0.3293 (3)0.6092 (12)0.0752 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0333 (4)0.0471 (4)0.0209 (3)0.0008 (3)0.0062 (3)0.0031 (3)
O10.042 (2)0.076 (3)0.0195 (18)0.004 (2)0.0038 (17)0.004 (2)
C10.039 (3)0.039 (3)0.025 (3)0.008 (2)0.003 (2)0.000 (2)
O20.041 (2)0.064 (3)0.034 (2)0.004 (2)0.004 (2)0.006 (2)
C20.040 (3)0.043 (3)0.029 (3)0.000 (2)0.004 (3)0.008 (3)
C30.086 (6)0.069 (5)0.075 (6)0.032 (4)0.024 (5)0.031 (5)
C40.101 (6)0.051 (4)0.122 (8)0.022 (4)0.030 (6)0.025 (5)
C50.061 (4)0.047 (3)0.057 (4)0.009 (3)0.002 (4)0.018 (3)
N10.044 (3)0.039 (2)0.020 (2)0.001 (2)0.004 (2)0.002 (2)
O30.042 (2)0.055 (3)0.0170 (16)0.002 (2)0.0052 (17)0.0010 (19)
C60.041 (3)0.034 (3)0.020 (2)0.007 (3)0.000 (2)0.001 (2)
O40.043 (2)0.077 (3)0.027 (2)0.011 (2)0.0027 (19)0.001 (3)
C70.029 (2)0.034 (3)0.023 (2)0.001 (2)0.010 (2)0.000 (2)
N20.036 (2)0.036 (2)0.024 (2)0.0036 (19)0.008 (2)0.0031 (19)
C80.034 (3)0.042 (3)0.032 (3)0.004 (2)0.004 (3)0.007 (3)
C90.040 (3)0.031 (3)0.029 (3)0.009 (2)0.002 (2)0.001 (2)
C100.052 (4)0.044 (3)0.034 (3)0.008 (3)0.007 (3)0.002 (3)
C110.067 (4)0.038 (3)0.051 (4)0.010 (3)0.005 (4)0.014 (3)
C120.063 (4)0.041 (3)0.074 (5)0.005 (3)0.000 (5)0.000 (4)
C130.071 (5)0.059 (4)0.053 (4)0.013 (4)0.017 (4)0.000 (4)
C140.063 (4)0.045 (3)0.035 (3)0.005 (3)0.011 (3)0.000 (3)
O50.042 (2)0.056 (3)0.066 (4)0.007 (2)0.010 (3)0.014 (3)
O60.063 (3)0.097 (4)0.065 (4)0.019 (3)0.000 (3)0.009 (3)
Geometric parameters (Å, º) top
Cu—O31.949 (4)C6—C71.530 (7)
Cu—O11.955 (4)C7—N21.470 (7)
Cu—N21.971 (5)C7—C81.532 (8)
Cu—N11.985 (5)C7—H70.9800
Cu—O52.338 (5)N2—H2A0.9000
O1—C11.276 (7)N2—H2B0.9000
C1—O21.232 (8)C8—C91.522 (8)
C1—C21.537 (8)C8—H8A0.9700
C2—N11.490 (8)C8—H8B0.9700
C2—C31.527 (10)C9—C101.377 (9)
C2—H20.9800C9—C141.386 (9)
C3—C41.493 (14)C10—C111.411 (10)
C3—H3A0.9700C10—H100.9300
C3—H3B0.9700C11—C121.386 (11)
C4—C51.458 (11)C11—H110.9300
C4—H4A0.9700C12—C131.370 (11)
C4—H4B0.9700C12—H120.9300
C5—N11.494 (8)C13—C141.389 (10)
C5—H5C0.9700C13—H130.9300
C5—H5D0.9700C14—H140.9300
N1—H10.9100O5—H5A0.75 (6)
O3—C61.279 (7)O5—H5B0.76 (6)
C6—O41.242 (7)
O3—Cu—O1175.2 (2)C6—O3—Cu114.6 (3)
O3—Cu—N284.7 (2)O4—C6—O3123.3 (5)
O1—Cu—N295.46 (19)O4—C6—C7119.4 (5)
O3—Cu—N193.55 (19)O3—C6—C7117.3 (5)
O1—Cu—N185.3 (2)N2—C7—C6108.5 (4)
N2—Cu—N1167.86 (18)N2—C7—C8114.4 (5)
O3—Cu—O592.0 (2)C6—C7—C8109.1 (5)
O1—Cu—O592.8 (2)N2—C7—H7108.2
N2—Cu—O593.77 (19)C6—C7—H7108.2
N1—Cu—O598.3 (2)C8—C7—H7108.2
C1—O1—Cu115.9 (4)C7—N2—Cu110.2 (3)
O2—C1—O1123.5 (6)C7—N2—H2A109.6
O2—C1—C2119.4 (6)Cu—N2—H2A109.6
O1—C1—C2117.0 (5)C7—N2—H2B109.6
N1—C2—C3107.4 (6)Cu—N2—H2B109.6
N1—C2—C1111.2 (5)H2A—N2—H2B108.1
C3—C2—C1111.7 (6)C9—C8—C7115.6 (4)
N1—C2—H2108.8C9—C8—H8A108.4
C3—C2—H2108.8C7—C8—H8A108.4
C1—C2—H2108.8C9—C8—H8B108.4
C4—C3—C2105.2 (7)C7—C8—H8B108.4
C4—C3—H3A110.7H8A—C8—H8B107.4
C2—C3—H3A110.7C10—C9—C14119.1 (6)
C4—C3—H3B110.7C10—C9—C8119.9 (6)
C2—C3—H3B110.7C14—C9—C8120.9 (6)
H3A—C3—H3B108.8C9—C10—C11119.8 (7)
C5—C4—C3107.7 (7)C9—C10—H10120.1
C5—C4—H4A110.2C11—C10—H10120.1
C3—C4—H4A110.2C12—C11—C10120.2 (7)
C5—C4—H4B110.2C12—C11—H11119.9
C3—C4—H4B110.2C10—C11—H11119.9
H4A—C4—H4B108.5C13—C12—C11119.6 (7)
C4—C5—N1106.9 (6)C13—C12—H12120.2
C4—C5—H5C110.3C11—C12—H12120.2
N1—C5—H5C110.3C12—C13—C14120.2 (7)
C4—C5—H5D110.3C12—C13—H13119.9
N1—C5—H5D110.3C14—C13—H13119.9
H5C—C5—H5D108.6C9—C14—C13121.1 (7)
C2—N1—C5106.6 (5)C9—C14—H14119.5
C2—N1—Cu109.7 (4)C13—C14—H14119.5
C5—N1—Cu112.9 (4)Cu—O5—H5A96 (7)
C2—N1—H1109.2Cu—O5—H5B133 (8)
C5—N1—H1109.2H5A—O5—H5B117 (10)
Cu—N1—H1109.2
N2—Cu—O1—C1175.1 (5)N2—Cu—O3—C62.2 (4)
N1—Cu—O1—C17.2 (5)N1—Cu—O3—C6165.7 (4)
O5—Cu—O1—C190.9 (5)O5—Cu—O3—C695.8 (4)
Cu—O1—C1—O2177.0 (5)Cu—O3—C6—O4172.0 (5)
Cu—O1—C1—C24.0 (7)Cu—O3—C6—C710.9 (7)
O2—C1—C2—N1175.8 (5)O4—C6—C7—N2160.4 (5)
O1—C1—C2—N13.2 (8)O3—C6—C7—N222.4 (8)
O2—C1—C2—C355.8 (9)O4—C6—C7—C874.4 (7)
O1—C1—C2—C3123.3 (7)O3—C6—C7—C8102.8 (6)
N1—C2—C3—C46.9 (10)C6—C7—N2—Cu22.4 (6)
C1—C2—C3—C4129.1 (8)C8—C7—N2—Cu99.6 (4)
C2—C3—C4—C520.1 (12)O3—Cu—N2—C714.6 (4)
C3—C4—C5—N125.7 (12)O1—Cu—N2—C7160.5 (4)
C3—C2—N1—C58.3 (8)N1—Cu—N2—C767.5 (11)
C1—C2—N1—C5114.2 (6)O5—Cu—N2—C7106.3 (4)
C3—C2—N1—Cu130.9 (6)N2—C7—C8—C959.3 (7)
C1—C2—N1—Cu8.4 (6)C6—C7—C8—C962.3 (7)
C4—C5—N1—C221.0 (10)C7—C8—C9—C1096.9 (7)
C4—C5—N1—Cu141.5 (8)C7—C8—C9—C1485.6 (7)
O3—Cu—N1—C2176.3 (4)C14—C9—C10—C111.2 (9)
O1—Cu—N1—C28.4 (4)C8—C9—C10—C11176.3 (6)
N2—Cu—N1—C2102.5 (10)C9—C10—C11—C120.3 (10)
O5—Cu—N1—C283.8 (4)C10—C11—C12—C131.8 (12)
O3—Cu—N1—C565.0 (5)C11—C12—C13—C141.7 (13)
O1—Cu—N1—C5110.3 (5)C10—C9—C14—C131.3 (10)
N2—Cu—N1—C516.2 (13)C8—C9—C14—C13176.2 (6)
O5—Cu—N1—C5157.5 (5)C12—C13—C14—C90.2 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.912.333.155 (7)150
N1—H1···O2i0.912.573.243 (7)131
N2—H2B···O3ii0.902.283.090 (7)150
N2—H2A···O2iii0.902.273.084 (6)150
O5—H5A···O4iv0.75 (6)1.98 (7)2.699 (7)160 (11)
O5—H5B···O6i0.76 (6)2.19 (9)2.858 (10)147 (11)
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1; (iii) x+1/2, y+1/2, z+1; (iv) x1/2, y+1/2, z.
 

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