Aqua­[2-(pyridin-2-yl­methyl­imino­methyl)­phenolato-κ³N,N′,O]copper(II) nitrate monohydrate

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.

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

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Computing details

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

Crystal data

[Cu(C13H11N2O)(H2O)](NO3)·H2O	Z = 2
Mr = 372.82	F(000) = 382
Triclinic, P1	Dx = 1.646 Mg m^−3
a = 7.777 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.993 (2) Å	Cell parameters from 3171 reflections
c = 11.389 (2) Å	θ = 2.4–26.8°
α = 71.25 (3)°	µ = 1.49 mm^−1
β = 86.18 (3)°	T = 293 K
γ = 86.88 (3)°	Block, blue
V = 752.2 (3) Å^3	0.27 × 0.23 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3044 independent reflections
Radiation source: fine-focus sealed tube	2816 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −9→9
Tmin = 0.690, Tmax = 0.808	k = −11→11
5940 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ^2(Fo^2) + (0.063P)^2 + 0.1843P] where P = (Fo^2 + 2Fc^2)/3
3044 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.62 e Å^−3
6 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.34402 (5)	0.40957 (4)	0.38261 (3)	0.04207 (17)
O1	0.3809 (3)	0.2648 (3)	0.5416 (2)	0.0529 (6)
O2	0.4878 (3)	0.2717 (3)	0.3081 (2)	0.0508 (6)
O3	0.1005 (4)	0.2444 (3)	0.3417 (3)	0.0723 (8)
O4	−0.0157 (4)	0.0773 (4)	0.2751 (3)	0.0809 (9)
O5	0.2487 (4)	0.1337 (3)	0.2236 (3)	0.0679 (7)
O6	0.3001 (4)	0.9474 (3)	0.5528 (3)	0.0642 (7)
N1	0.2915 (4)	0.5678 (3)	0.2199 (3)	0.0472 (6)
N2	0.2358 (3)	0.5673 (3)	0.4470 (3)	0.0423 (6)
N3	0.1106 (4)	0.1523 (3)	0.2800 (3)	0.0524 (7)
C1	0.2550 (4)	0.4206 (4)	0.6645 (3)	0.0450 (7)
C2	0.2138 (5)	0.4290 (5)	0.7844 (3)	0.0577 (9)
H2	0.1557	0.5185	0.7929	0.069*
C3	0.2562 (5)	0.3103 (5)	0.8884 (4)	0.0662 (11)
H3	0.2265	0.3177	0.9669	0.079*
C4	0.3442 (5)	0.1789 (5)	0.8751 (4)	0.0637 (10)
H4	0.3762	0.0984	0.9457	0.076*
C5	0.3859 (5)	0.1637 (4)	0.7594 (4)	0.0607 (10)
H5	0.4443	0.0732	0.7534	0.073*
C6	0.3408 (4)	0.2837 (4)	0.6512 (3)	0.0461 (7)
C7	0.2085 (4)	0.5539 (4)	0.5621 (3)	0.0448 (7)
H7	0.1534	0.6387	0.5806	0.054*
C8	0.1839 (5)	0.7159 (3)	0.3541 (3)	0.0488 (8)
H8A	0.2506	0.8004	0.3609	0.059*
H8B	0.0629	0.7402	0.3687	0.059*
C9	0.2133 (4)	0.7019 (3)	0.2268 (3)	0.0437 (7)
C10	0.1646 (5)	0.8202 (4)	0.1215 (4)	0.0567 (9)
H10	0.1129	0.9131	0.1281	0.068*
C11	0.1926 (5)	0.8006 (4)	0.0079 (4)	0.0634 (10)
H11	0.1578	0.8782	−0.0635	0.076*
C12	0.2733 (6)	0.6634 (5)	0.0011 (4)	0.0663 (10)
H12	0.2951	0.6479	−0.0755	0.080*
C13	0.3212 (5)	0.5505 (4)	0.1069 (4)	0.0597 (9)
H13	0.3761	0.4585	0.1010	0.072*
H2A	0.414 (4)	0.219 (4)	0.280 (4)	0.080*
H6B	0.200 (3)	0.933 (4)	0.598 (4)	0.080*
H2B	0.555 (5)	0.204 (3)	0.362 (3)	0.080*
H6A	0.333 (5)	1.045 (2)	0.545 (4)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0479 (3)	0.0276 (2)	0.0502 (3)	0.00473 (15)	−0.00089 (17)	−0.01292 (16)
O1	0.0691 (16)	0.0320 (11)	0.0538 (14)	0.0103 (10)	−0.0030 (12)	−0.0103 (10)
O2	0.0516 (14)	0.0385 (12)	0.0636 (15)	0.0053 (10)	0.0001 (11)	−0.0197 (11)
O3	0.0619 (16)	0.0589 (16)	0.107 (2)	0.0019 (13)	0.0103 (15)	−0.0453 (17)
O4	0.0613 (18)	0.099 (2)	0.096 (2)	−0.0150 (16)	−0.0045 (16)	−0.0470 (19)
O5	0.0657 (17)	0.0735 (18)	0.0763 (19)	−0.0024 (14)	0.0068 (14)	−0.0426 (15)
O6	0.0669 (17)	0.0421 (13)	0.0818 (19)	0.0090 (12)	−0.0019 (14)	−0.0194 (13)
N1	0.0547 (16)	0.0331 (13)	0.0538 (16)	−0.0001 (11)	−0.0026 (13)	−0.0140 (12)
N2	0.0447 (14)	0.0310 (12)	0.0518 (16)	0.0039 (11)	−0.0031 (12)	−0.0150 (11)
N3	0.0556 (18)	0.0431 (15)	0.0571 (18)	0.0082 (13)	−0.0100 (14)	−0.0141 (13)
C1	0.0450 (17)	0.0401 (16)	0.0510 (19)	−0.0040 (13)	−0.0036 (14)	−0.0155 (14)
C2	0.065 (2)	0.058 (2)	0.054 (2)	−0.0026 (18)	−0.0025 (17)	−0.0231 (17)
C3	0.077 (3)	0.072 (3)	0.049 (2)	−0.020 (2)	−0.0001 (19)	−0.0166 (19)
C4	0.077 (3)	0.055 (2)	0.052 (2)	−0.0174 (19)	−0.0088 (19)	−0.0035 (17)
C5	0.066 (2)	0.0386 (18)	0.071 (3)	−0.0025 (16)	−0.0109 (19)	−0.0063 (17)
C6	0.0473 (18)	0.0355 (16)	0.055 (2)	−0.0052 (13)	−0.0040 (15)	−0.0127 (14)
C7	0.0446 (17)	0.0370 (15)	0.057 (2)	0.0011 (13)	−0.0030 (14)	−0.0215 (14)
C8	0.057 (2)	0.0288 (14)	0.059 (2)	0.0080 (13)	−0.0057 (16)	−0.0131 (14)
C9	0.0482 (17)	0.0308 (14)	0.0515 (18)	−0.0002 (13)	−0.0095 (14)	−0.0109 (13)
C10	0.071 (2)	0.0351 (16)	0.064 (2)	0.0051 (16)	−0.0184 (18)	−0.0135 (15)
C11	0.079 (3)	0.048 (2)	0.059 (2)	−0.0026 (18)	−0.020 (2)	−0.0071 (17)
C12	0.090 (3)	0.061 (2)	0.050 (2)	−0.007 (2)	−0.008 (2)	−0.0187 (18)
C13	0.079 (3)	0.0465 (19)	0.056 (2)	0.0026 (18)	−0.0018 (19)	−0.0209 (17)

Geometric parameters (Å, º)

Cu1—O1	1.889 (2)	C2—H2	0.9300
Cu1—N2	1.927 (3)	C3—C4	1.379 (6)
Cu1—O2	1.977 (2)	C3—H3	0.9300
Cu1—N1	1.993 (3)	C4—C5	1.383 (6)
O1—C6	1.328 (4)	C4—H4	0.9300
O2—H2A	0.897 (10)	C5—C6	1.403 (5)
O2—H2B	0.892 (10)	C5—H5	0.9300
O3—N3	1.243 (4)	C7—H7	0.9300
O4—N3	1.236 (4)	C8—C9	1.496 (5)
O5—N3	1.246 (4)	C8—H8A	0.9700
O6—H6B	0.896 (10)	C8—H8B	0.9700
O6—H6A	0.900 (10)	C9—C10	1.382 (5)
N1—C9	1.344 (4)	C10—C11	1.363 (5)
N1—C13	1.349 (5)	C10—H10	0.9300
N2—C7	1.282 (4)	C11—C12	1.375 (6)
N2—C8	1.469 (4)	C11—H11	0.9300
C1—C2	1.406 (5)	C12—C13	1.362 (5)
C1—C6	1.415 (4)	C12—H12	0.9300
C1—C7	1.428 (5)	C13—H13	0.9300
C2—C3	1.361 (5)
O1—Cu1—N2	93.93 (11)	C5—C4—H4	119.2
O1—Cu1—O2	89.19 (11)	C4—C5—C6	120.5 (4)
N2—Cu1—O2	170.39 (10)	C4—C5—H5	119.7
O1—Cu1—N1	176.23 (10)	C6—C5—H5	119.7
N2—Cu1—N1	82.80 (11)	O1—C6—C5	119.1 (3)
O2—Cu1—N1	94.35 (11)	O1—C6—C1	123.1 (3)
C6—O1—Cu1	127.7 (2)	C5—C6—C1	117.9 (3)
Cu1—O2—H2A	106 (3)	N2—C7—C1	125.9 (3)
Cu1—O2—H2B	113 (3)	N2—C7—H7	117.1
H2A—O2—H2B	110 (2)	C1—C7—H7	117.1
H6B—O6—H6A	107 (2)	N2—C8—C9	109.6 (2)
C9—N1—C13	118.3 (3)	N2—C8—H8A	109.8
C9—N1—Cu1	115.1 (2)	C9—C8—H8A	109.8
C13—N1—Cu1	126.6 (2)	N2—C8—H8B	109.8
C7—N2—C8	118.2 (3)	C9—C8—H8B	109.8
C7—N2—Cu1	125.8 (2)	H8A—C8—H8B	108.2
C8—N2—Cu1	116.0 (2)	N1—C9—C10	121.4 (3)
O4—N3—O3	120.3 (3)	N1—C9—C8	116.3 (3)
O4—N3—O5	119.4 (3)	C10—C9—C8	122.3 (3)
O3—N3—O5	120.3 (3)	C11—C10—C9	119.9 (3)
C2—C1—C6	119.2 (3)	C11—C10—H10	120.0
C2—C1—C7	117.2 (3)	C9—C10—H10	120.0
C6—C1—C7	123.6 (3)	C10—C11—C12	118.6 (4)
C3—C2—C1	122.0 (4)	C10—C11—H11	120.7
C3—C2—H2	119.0	C12—C11—H11	120.7
C1—C2—H2	119.0	C13—C12—C11	119.8 (4)
C2—C3—C4	118.6 (4)	C13—C12—H12	120.1
C2—C3—H3	120.7	C11—C12—H12	120.1
C4—C3—H3	120.7	N1—C13—C12	122.1 (3)
C3—C4—C5	121.6 (4)	N1—C13—H13	119.0
C3—C4—H4	119.2	C12—C13—H13	119.0
N2—Cu1—O1—C6	−0.8 (3)	C2—C1—C6—O1	178.5 (3)
O2—Cu1—O1—C6	170.1 (3)	C7—C1—C6—O1	−2.3 (5)
N1—Cu1—O1—C6	−30.3 (16)	C2—C1—C6—C5	−1.9 (5)
O1—Cu1—N1—C9	30.3 (16)	C7—C1—C6—C5	177.3 (3)
N2—Cu1—N1—C9	0.7 (2)	C8—N2—C7—C1	−178.0 (3)
O2—Cu1—N1—C9	−170.1 (2)	Cu1—N2—C7—C1	0.8 (5)
O1—Cu1—N1—C13	−147.2 (14)	C2—C1—C7—N2	179.9 (3)
N2—Cu1—N1—C13	−176.9 (3)	C6—C1—C7—N2	0.7 (5)
O2—Cu1—N1—C13	12.4 (3)	C7—N2—C8—C9	−175.3 (3)
O1—Cu1—N2—C7	−0.8 (3)	Cu1—N2—C8—C9	5.8 (3)
O2—Cu1—N2—C7	−109.4 (6)	C13—N1—C9—C10	−0.3 (5)
N1—Cu1—N2—C7	177.4 (3)	Cu1—N1—C9—C10	−178.1 (3)
O1—Cu1—N2—C8	178.1 (2)	C13—N1—C9—C8	−179.7 (3)
O2—Cu1—N2—C8	69.5 (7)	Cu1—N1—C9—C8	2.5 (4)
N1—Cu1—N2—C8	−3.7 (2)	N2—C8—C9—N1	−5.3 (4)
C6—C1—C2—C3	1.0 (5)	N2—C8—C9—C10	175.3 (3)
C7—C1—C2—C3	−178.3 (3)	N1—C9—C10—C11	1.4 (6)
C1—C2—C3—C4	0.8 (6)	C8—C9—C10—C11	−179.2 (3)
C2—C3—C4—C5	−1.6 (6)	C9—C10—C11—C12	−1.6 (6)
C3—C4—C5—C6	0.6 (6)	C10—C11—C12—C13	0.8 (6)
Cu1—O1—C6—C5	−177.3 (2)	C9—N1—C13—C12	−0.5 (6)
Cu1—O1—C6—C1	2.3 (5)	Cu1—N1—C13—C12	176.9 (3)
C4—C5—C6—O1	−179.2 (3)	C11—C12—C13—N1	0.3 (6)
C4—C5—C6—C1	1.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O5	0.90 (1)	1.79 (1)	2.680 (4)	173 (4)
O2—H2A···N3	0.90 (1)	2.47 (3)	3.248 (4)	146 (4)
O2—H2A···O3	0.90 (1)	2.51 (4)	3.024 (4)	117 (3)
O6—H6B···O4^i	0.90 (1)	1.95 (2)	2.825 (4)	165 (4)
O2—H2B···O6^ii	0.89 (1)	1.78 (1)	2.665 (4)	169 (4)
O6—H6A···O1^iii	0.90 (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.