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The title compound, [Cu(C13H11N2O)(H2O)](NO3)·H2O, is a mononuclear copper(II) compound. The Cu atom is coordinated by two N atoms and one O atom from the Schiff base ligand, and another O atom from a water mol­ecule. The four atoms around the metal constitute a slightly distorted square-planar geometry. All O atoms in the nitrate anions and all amine N atoms in the 2-amino­methyl­pyridine ligands contribute to hydrogen bonds, leading to the formation of sheets parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401284X/ac6102sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680401284X/ac6102Isup2.hkl
Contains datablock I

CCDC reference: 242295

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.124
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.43 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O3 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N3 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3 N1 -CU1 -O1 -C6 -30.30 1.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 O1 -CU1 -N1 -C9 30.30 1.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 7 O1 -CU1 -N1 -C13 -147.20 1.40 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 O2 -CU1 -N2 -C7 -109.40 0.60 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 O2 -CU1 -N2 -C8 69.50 0.70 1.555 1.555 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.90(4), Rep 0.897(10) ...... 4.00 su-Rat O2 -H2A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.89(3), Rep 0.892(10) ...... 3.00 su-Rat O2 -H2B 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.90(3), Rep 0.896(10) ...... 3.00 su-Rat O6 -H6B 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.90(3), Rep 0.900(10) ...... 3.00 su-Rat O6 -H6A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.90(4), Rep 0.897(10) ...... 4.00 su-Rat O2 -H2A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.90(4), Rep 0.897(10) ...... 4.00 su-Rat O2 -H2A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.90(4), Rep 0.897(10) ...... 4.00 su-Rat O2 -H2A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.90(3), Rep 0.896(10) ...... 3.00 su-Rat O6 -H6B 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(3), Rep 0.892(10) ...... 3.00 su-Rat O2 -H2B 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.90(3), Rep 0.900(10) ...... 3.00 su-Rat O6 -H6A 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.79(4), Rep 1.787(11) ...... 3.64 su-Rat H2A -O5 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.79(3), Rep 1.784(14) ...... 2.14 su-Rat H2B -O6 1.555 2.666
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C13 H15 Cu1 N3 O6 Atom count from _chemical_formula_moiety:
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 23 ALERT level C = Check and explain 1 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 6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Aqua[2-(pyridin-2-ylmethyliminomethyl)phenolato-κ3N,N',O]copper(II) nitrate monohydrate top
Crystal data top
[Cu(C13H11N2O)(H2O)](NO3)·H2OZ = 2
Mr = 372.82F(000) = 382
Triclinic, P1Dx = 1.646 Mg m3
a = 7.777 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.993 (2) ÅCell parameters from 3171 reflections
c = 11.389 (2) Åθ = 2.4–26.8°
α = 71.25 (3)°µ = 1.49 mm1
β = 86.18 (3)°T = 293 K
γ = 86.88 (3)°Block, blue
V = 752.2 (3) Å30.27 × 0.23 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3044 independent reflections
Radiation source: fine-focus sealed tube2816 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Blessing, 1995)
h = 99
Tmin = 0.690, Tmax = 0.808k = 1111
5940 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.18 w = 1/[σ2(Fo2) + (0.063P)2 + 0.1843P]
where P = (Fo2 + 2Fc2)/3
3044 reflections(Δ/σ)max < 0.001
220 parametersΔρmax = 0.62 e Å3
6 restraintsΔρmin = 0.25 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.34402 (5)0.40957 (4)0.38261 (3)0.04207 (17)
O10.3809 (3)0.2648 (3)0.5416 (2)0.0529 (6)
O20.4878 (3)0.2717 (3)0.3081 (2)0.0508 (6)
O30.1005 (4)0.2444 (3)0.3417 (3)0.0723 (8)
O40.0157 (4)0.0773 (4)0.2751 (3)0.0809 (9)
O50.2487 (4)0.1337 (3)0.2236 (3)0.0679 (7)
O60.3001 (4)0.9474 (3)0.5528 (3)0.0642 (7)
N10.2915 (4)0.5678 (3)0.2199 (3)0.0472 (6)
N20.2358 (3)0.5673 (3)0.4470 (3)0.0423 (6)
N30.1106 (4)0.1523 (3)0.2800 (3)0.0524 (7)
C10.2550 (4)0.4206 (4)0.6645 (3)0.0450 (7)
C20.2138 (5)0.4290 (5)0.7844 (3)0.0577 (9)
H20.15570.51850.79290.069*
C30.2562 (5)0.3103 (5)0.8884 (4)0.0662 (11)
H30.22650.31770.96690.079*
C40.3442 (5)0.1789 (5)0.8751 (4)0.0637 (10)
H40.37620.09840.94570.076*
C50.3859 (5)0.1637 (4)0.7594 (4)0.0607 (10)
H50.44430.07320.75340.073*
C60.3408 (4)0.2837 (4)0.6512 (3)0.0461 (7)
C70.2085 (4)0.5539 (4)0.5621 (3)0.0448 (7)
H70.15340.63870.58060.054*
C80.1839 (5)0.7159 (3)0.3541 (3)0.0488 (8)
H8A0.25060.80040.36090.059*
H8B0.06290.74020.36870.059*
C90.2133 (4)0.7019 (3)0.2268 (3)0.0437 (7)
C100.1646 (5)0.8202 (4)0.1215 (4)0.0567 (9)
H100.11290.91310.12810.068*
C110.1926 (5)0.8006 (4)0.0079 (4)0.0634 (10)
H110.15780.87820.06350.076*
C120.2733 (6)0.6634 (5)0.0011 (4)0.0663 (10)
H120.29510.64790.07550.080*
C130.3212 (5)0.5505 (4)0.1069 (4)0.0597 (9)
H130.37610.45850.10100.072*
H2A0.414 (4)0.219 (4)0.280 (4)0.080*
H6B0.200 (3)0.933 (4)0.598 (4)0.080*
H2B0.555 (5)0.204 (3)0.362 (3)0.080*
H6A0.333 (5)1.045 (2)0.545 (4)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0479 (3)0.0276 (2)0.0502 (3)0.00473 (15)0.00089 (17)0.01292 (16)
O10.0691 (16)0.0320 (11)0.0538 (14)0.0103 (10)0.0030 (12)0.0103 (10)
O20.0516 (14)0.0385 (12)0.0636 (15)0.0053 (10)0.0001 (11)0.0197 (11)
O30.0619 (16)0.0589 (16)0.107 (2)0.0019 (13)0.0103 (15)0.0453 (17)
O40.0613 (18)0.099 (2)0.096 (2)0.0150 (16)0.0045 (16)0.0470 (19)
O50.0657 (17)0.0735 (18)0.0763 (19)0.0024 (14)0.0068 (14)0.0426 (15)
O60.0669 (17)0.0421 (13)0.0818 (19)0.0090 (12)0.0019 (14)0.0194 (13)
N10.0547 (16)0.0331 (13)0.0538 (16)0.0001 (11)0.0026 (13)0.0140 (12)
N20.0447 (14)0.0310 (12)0.0518 (16)0.0039 (11)0.0031 (12)0.0150 (11)
N30.0556 (18)0.0431 (15)0.0571 (18)0.0082 (13)0.0100 (14)0.0141 (13)
C10.0450 (17)0.0401 (16)0.0510 (19)0.0040 (13)0.0036 (14)0.0155 (14)
C20.065 (2)0.058 (2)0.054 (2)0.0026 (18)0.0025 (17)0.0231 (17)
C30.077 (3)0.072 (3)0.049 (2)0.020 (2)0.0001 (19)0.0166 (19)
C40.077 (3)0.055 (2)0.052 (2)0.0174 (19)0.0088 (19)0.0035 (17)
C50.066 (2)0.0386 (18)0.071 (3)0.0025 (16)0.0109 (19)0.0063 (17)
C60.0473 (18)0.0355 (16)0.055 (2)0.0052 (13)0.0040 (15)0.0127 (14)
C70.0446 (17)0.0370 (15)0.057 (2)0.0011 (13)0.0030 (14)0.0215 (14)
C80.057 (2)0.0288 (14)0.059 (2)0.0080 (13)0.0057 (16)0.0131 (14)
C90.0482 (17)0.0308 (14)0.0515 (18)0.0002 (13)0.0095 (14)0.0109 (13)
C100.071 (2)0.0351 (16)0.064 (2)0.0051 (16)0.0184 (18)0.0135 (15)
C110.079 (3)0.048 (2)0.059 (2)0.0026 (18)0.020 (2)0.0071 (17)
C120.090 (3)0.061 (2)0.050 (2)0.007 (2)0.008 (2)0.0187 (18)
C130.079 (3)0.0465 (19)0.056 (2)0.0026 (18)0.0018 (19)0.0209 (17)
Geometric parameters (Å, º) top
Cu1—O11.889 (2)C2—H20.9300
Cu1—N21.927 (3)C3—C41.379 (6)
Cu1—O21.977 (2)C3—H30.9300
Cu1—N11.993 (3)C4—C51.383 (6)
O1—C61.328 (4)C4—H40.9300
O2—H2A0.897 (10)C5—C61.403 (5)
O2—H2B0.892 (10)C5—H50.9300
O3—N31.243 (4)C7—H70.9300
O4—N31.236 (4)C8—C91.496 (5)
O5—N31.246 (4)C8—H8A0.9700
O6—H6B0.896 (10)C8—H8B0.9700
O6—H6A0.900 (10)C9—C101.382 (5)
N1—C91.344 (4)C10—C111.363 (5)
N1—C131.349 (5)C10—H100.9300
N2—C71.282 (4)C11—C121.375 (6)
N2—C81.469 (4)C11—H110.9300
C1—C21.406 (5)C12—C131.362 (5)
C1—C61.415 (4)C12—H120.9300
C1—C71.428 (5)C13—H130.9300
C2—C31.361 (5)
O1—Cu1—N293.93 (11)C5—C4—H4119.2
O1—Cu1—O289.19 (11)C4—C5—C6120.5 (4)
N2—Cu1—O2170.39 (10)C4—C5—H5119.7
O1—Cu1—N1176.23 (10)C6—C5—H5119.7
N2—Cu1—N182.80 (11)O1—C6—C5119.1 (3)
O2—Cu1—N194.35 (11)O1—C6—C1123.1 (3)
C6—O1—Cu1127.7 (2)C5—C6—C1117.9 (3)
Cu1—O2—H2A106 (3)N2—C7—C1125.9 (3)
Cu1—O2—H2B113 (3)N2—C7—H7117.1
H2A—O2—H2B110 (2)C1—C7—H7117.1
H6B—O6—H6A107 (2)N2—C8—C9109.6 (2)
C9—N1—C13118.3 (3)N2—C8—H8A109.8
C9—N1—Cu1115.1 (2)C9—C8—H8A109.8
C13—N1—Cu1126.6 (2)N2—C8—H8B109.8
C7—N2—C8118.2 (3)C9—C8—H8B109.8
C7—N2—Cu1125.8 (2)H8A—C8—H8B108.2
C8—N2—Cu1116.0 (2)N1—C9—C10121.4 (3)
O4—N3—O3120.3 (3)N1—C9—C8116.3 (3)
O4—N3—O5119.4 (3)C10—C9—C8122.3 (3)
O3—N3—O5120.3 (3)C11—C10—C9119.9 (3)
C2—C1—C6119.2 (3)C11—C10—H10120.0
C2—C1—C7117.2 (3)C9—C10—H10120.0
C6—C1—C7123.6 (3)C10—C11—C12118.6 (4)
C3—C2—C1122.0 (4)C10—C11—H11120.7
C3—C2—H2119.0C12—C11—H11120.7
C1—C2—H2119.0C13—C12—C11119.8 (4)
C2—C3—C4118.6 (4)C13—C12—H12120.1
C2—C3—H3120.7C11—C12—H12120.1
C4—C3—H3120.7N1—C13—C12122.1 (3)
C3—C4—C5121.6 (4)N1—C13—H13119.0
C3—C4—H4119.2C12—C13—H13119.0
N2—Cu1—O1—C60.8 (3)C2—C1—C6—O1178.5 (3)
O2—Cu1—O1—C6170.1 (3)C7—C1—C6—O12.3 (5)
N1—Cu1—O1—C630.3 (16)C2—C1—C6—C51.9 (5)
O1—Cu1—N1—C930.3 (16)C7—C1—C6—C5177.3 (3)
N2—Cu1—N1—C90.7 (2)C8—N2—C7—C1178.0 (3)
O2—Cu1—N1—C9170.1 (2)Cu1—N2—C7—C10.8 (5)
O1—Cu1—N1—C13147.2 (14)C2—C1—C7—N2179.9 (3)
N2—Cu1—N1—C13176.9 (3)C6—C1—C7—N20.7 (5)
O2—Cu1—N1—C1312.4 (3)C7—N2—C8—C9175.3 (3)
O1—Cu1—N2—C70.8 (3)Cu1—N2—C8—C95.8 (3)
O2—Cu1—N2—C7109.4 (6)C13—N1—C9—C100.3 (5)
N1—Cu1—N2—C7177.4 (3)Cu1—N1—C9—C10178.1 (3)
O1—Cu1—N2—C8178.1 (2)C13—N1—C9—C8179.7 (3)
O2—Cu1—N2—C869.5 (7)Cu1—N1—C9—C82.5 (4)
N1—Cu1—N2—C83.7 (2)N2—C8—C9—N15.3 (4)
C6—C1—C2—C31.0 (5)N2—C8—C9—C10175.3 (3)
C7—C1—C2—C3178.3 (3)N1—C9—C10—C111.4 (6)
C1—C2—C3—C40.8 (6)C8—C9—C10—C11179.2 (3)
C2—C3—C4—C51.6 (6)C9—C10—C11—C121.6 (6)
C3—C4—C5—C60.6 (6)C10—C11—C12—C130.8 (6)
Cu1—O1—C6—C5177.3 (2)C9—N1—C13—C120.5 (6)
Cu1—O1—C6—C12.3 (5)Cu1—N1—C13—C12176.9 (3)
C4—C5—C6—O1179.2 (3)C11—C12—C13—N10.3 (6)
C4—C5—C6—C11.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O50.90 (1)1.79 (1)2.680 (4)173 (4)
O2—H2A···N30.90 (1)2.47 (3)3.248 (4)146 (4)
O2—H2A···O30.90 (1)2.51 (4)3.024 (4)117 (3)
O6—H6B···O4i0.90 (1)1.95 (2)2.825 (4)165 (4)
O2—H2B···O6ii0.89 (1)1.78 (1)2.665 (4)169 (4)
O6—H6A···O1iii0.90 (1)2.02 (1)2.917 (3)173 (3)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x, y+1, z.
 

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