Bis[2-(hydroxy­meth­yl)pyridine-κ²N,O]dinitratocopper(II)

In the crystal structure of the title compound, [Cu(NO₃)₂(C₆H₇NO)₂], the copper(II) ion resides at an inversion centre and it has a 4 + 2 elongated ocatahedral coordination environment. The equatorial positions are occupied by two OH groups and two N atoms from a pair of neutral 2-(hydroxy­meth­yl)pyridine ligands, while the two axial positions are weakly ligated by two nitrate O atoms. Adjacent mononuclear copper(II) complexes are further joined together by O—H...O hydrogen bonds to form a linear chain along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
Some non-H atoms missing
• R factor = 0.025
• wR factor = 0.076
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level A
ABSMU01_ALERT_1_A  The ratio of given/expected absorption coefficient lies
               outside the range 0.90 <> 1.10
            Calculated value of mu =     2.970
            Value of mu given      =     1.485
CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.90 <> 1.10
           From the CIF: _cell_formula_units_Z                    4
           From the CIF: _chemical_formula_weight           405.82
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01    6.00   72.07
           H         1.01    7.00    7.06
           N        14.01    2.00   28.01
           O        16.00    4.00   64.00
           Cu       63.55    0.50   31.77
           Calculated formula weight              202.90
DENSD01_ALERT_1_A  The ratio of the submitted crystal density and that
            calculated from the formula is outside the range 0.90 <> 1.10
            Crystal density given    =      1.767
            Calculated crystal density =      3.533
PLAT043_ALERT_1_A Check Reported Molecular Weight ................     405.82
PLAT046_ALERT_1_A Reported Z, MW and D(calc) are Inconsistent ....       3.53
PLAT731_ALERT_1_A Bond    Calc  1.4245(18), Rep 1.42450(10) ......       9.90 su-Rat
              O1   -C1      1.555   1.555

Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            deep
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT145_ALERT_4_C su on beta     Small or Missing  (x 10000) .....          1 Deg.
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O1      ..       6.97 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            O1  -CU1 -O1  -C1      5.00  0.00   3.666   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            N1  -CU1 -N1  -C2     17.00  0.00   3.666   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          7
            N1  -CU1 -N1  -C6      0.00  0.00   3.666   1.555   1.555   1.555

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:C12 H14 Cu1 N4 O8
            Atom count from the _atom_site data:  C6 H7 Cu0.5 N2 O4
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C12 H14 Cu N4 O8
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         48.00     24.00   24.00
           H         56.00     28.00   28.00
           Cu         4.00      2.00    2.00
           N         16.00      8.00    8.00
           O         32.00     16.00   16.00

   6 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

  11 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
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXL97.

Bis[2-(hydroxymethyl)pyridine-κ²N,O]dinitratocopper(II)

Crystal data

[Cu(NO3)2(C6H7NO)2]	F(000) = 414
Mr = 405.82	Dx = 1.767 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3474 reflections
a = 7.4402 (5) Å	θ = 2.5–28.2°
b = 12.4849 (9) Å	µ = 1.49 mm^−1
c = 8.4844 (6) Å	T = 293 K
β = 104.5240 (1)°	Polyhedron, deep blue
V = 762.93 (9) Å^3	0.39 × 0.36 × 0.23 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	1712 independent reflections
Radiation source: fine-focus sealed tube	1593 reflections with I > 2˘I)
Graphite monochromator	Rint = 0.013
φ and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→9
Tmin = 0.593, Tmax = 0.726	k = −15→15
4602 measured reflections	l = −10→9

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 0.1296P] where P = (Fo^2 + 2Fc^2)/3
1712 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.28 e Å^−3
1 restraint	Δρmin = −0.31 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	0.5000	0.5000	0.5000	0.03274 (12)
O1	0.62504 (14)	0.62944 (8)	0.44707 (12)	0.0371 (2)
H1	0.7403 (14)	0.6233 (15)	0.461 (2)	0.043 (5)*
N1	0.39321 (19)	0.49814 (8)	0.26507 (18)	0.0326 (3)
C1	0.5426 (2)	0.67067 (12)	0.28890 (18)	0.0425 (3)
H1A	0.6392	0.6912	0.2364	0.051*
H1B	0.4704	0.7340	0.2981	0.051*
C2	0.41891 (19)	0.58785 (11)	0.18706 (17)	0.0348 (3)
C3	0.3378 (2)	0.60158 (13)	0.02223 (18)	0.0430 (3)
H3	0.3556	0.6647	−0.0300	0.052*
C4	0.2305 (2)	0.52029 (15)	−0.0629 (2)	0.0472 (4)
H4	0.1737	0.5283	−0.1731	0.057*
C5	0.2081 (2)	0.42644 (15)	0.01745 (18)	0.0479 (4)
H5	0.1376	0.3703	−0.0382	0.058*
C6	0.2921 (2)	0.41780 (13)	0.18074 (18)	0.0415 (3)
H6	0.2787	0.3546	0.2347	0.050*
N2	0.09078 (17)	0.63407 (10)	0.47588 (15)	0.0378 (3)
O2	0.25894 (16)	0.62575 (13)	0.54369 (19)	0.0627 (4)
O3	−0.02307 (16)	0.61935 (11)	0.56122 (15)	0.0517 (3)
O4	0.0353 (2)	0.65843 (14)	0.33405 (17)	0.0783 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.02691 (16)	0.04410 (18)	0.02574 (16)	−0.00666 (8)	0.00382 (11)	0.00243 (8)
O1	0.0279 (5)	0.0465 (6)	0.0350 (5)	−0.0039 (4)	0.0044 (4)	0.0044 (4)
N1	0.0254 (6)	0.0434 (7)	0.0282 (7)	−0.0013 (4)	0.0051 (5)	0.0008 (4)
C1	0.0445 (8)	0.0394 (7)	0.0393 (8)	0.0025 (6)	0.0025 (6)	0.0071 (6)
C2	0.0276 (6)	0.0427 (7)	0.0336 (7)	0.0068 (5)	0.0069 (5)	0.0039 (5)
C3	0.0391 (7)	0.0543 (8)	0.0342 (7)	0.0113 (6)	0.0064 (6)	0.0093 (6)
C4	0.0346 (8)	0.0761 (11)	0.0281 (8)	0.0089 (7)	0.0025 (6)	0.0011 (7)
C5	0.0357 (8)	0.0706 (11)	0.0361 (8)	−0.0078 (7)	0.0065 (6)	−0.0089 (7)
C6	0.0354 (7)	0.0547 (8)	0.0343 (7)	−0.0101 (6)	0.0086 (6)	−0.0032 (6)
N2	0.0329 (6)	0.0404 (6)	0.0387 (6)	0.0008 (5)	0.0066 (5)	−0.0076 (5)
O2	0.0276 (6)	0.0863 (10)	0.0707 (9)	0.0050 (6)	0.0060 (6)	−0.0212 (7)
O3	0.0351 (6)	0.0752 (8)	0.0448 (7)	−0.0015 (5)	0.0102 (5)	−0.0024 (6)
O4	0.0759 (10)	0.1104 (12)	0.0439 (8)	−0.0091 (9)	0.0060 (7)	0.0129 (7)

Geometric parameters (Å, º)

Cu1—N1	1.952 (1)	C2—C3	1.388 (2)
Cu1—N1^i	1.952 (1)	C3—C4	1.378 (2)
Cu1—O1	1.971 (1)	C3—H3	0.9300
Cu1—O1^i	1.971 (1)	C4—C5	1.386 (3)
O1—C1	1.4245 (1)	C4—H4	0.9300
O1—H1	0.840 (9)	C5—C6	1.374 (2)
N1—C2	1.338 (2)	C5—H5	0.9300
N1—C6	1.346 (2)	C6—H6	0.9300
C1—C2	1.505 (2)	N2—O4	1.209 (2)
C1—H1A	0.9700	N2—O2	1.243 (2)
C1—H1B	0.9700	N2—O3	1.258 (2)
N1—Cu1—N1^i	180.0	N1—C2—C3	121.44 (14)
N1—Cu1—O1	82.63 (4)	N1—C2—C1	115.70 (12)
N1^i—Cu1—O1^i	82.63 (4)	C3—C2—C1	122.85 (13)
N1—Cu1—O1^i	97.37 (4)	C4—C3—C2	119.03 (15)
N1^i—Cu1—O1	97.37 (4)	C4—C3—H3	120.5
O1—Cu1—O1^i	180.0	C2—C3—H3	120.5
C1—O1—Cu1	113.23 (8)	C3—C4—C5	119.34 (16)
C1—O1—H1	110.3 (13)	C3—C4—H4	120.3
Cu1—O1—H1	114.7 (13)	C5—C4—H4	120.3
C2—N1—C6	119.37 (14)	C6—C5—C4	118.81 (15)
C2—N1—Cu1	115.01 (10)	C6—C5—H5	120.6
C6—N1—Cu1	125.55 (10)	C4—C5—H5	120.6
O1—C1—C2	110.46 (11)	N1—C6—C5	121.97 (15)
O1—C1—H1A	109.6	N1—C6—H6	119.0
C2—C1—H1A	109.6	C5—C6—H6	119.0
O1—C1—H1B	109.6	O4—N2—O2	122.30 (15)
C2—C1—H1B	109.6	O4—N2—O3	119.89 (13)
H1A—C1—H1B	108.1	O2—N2—O3	117.77 (14)
N1—Cu1—O1—C1	16.04 (10)	C6—N1—C2—C1	−176.62 (14)
N1^i—Cu1—O1—C1	−163.96 (10)	Cu1—N1—C2—C1	6.33 (16)
O1^i—Cu1—O1—C1	50 (100)	O1—C1—C2—N1	6.74 (18)
N1^i—Cu1—N1—C2	174 (100)	O1—C1—C2—C3	−172.32 (13)
O1—Cu1—N1—C2	−12.35 (10)	N1—C2—C3—C4	−0.8 (2)
O1^i—Cu1—N1—C2	167.65 (10)	C1—C2—C3—C4	178.19 (15)
N1^i—Cu1—N1—C6	−2 (100)	C2—C3—C4—C5	−0.8 (2)
O1—Cu1—N1—C6	170.82 (13)	C3—C4—C5—C6	0.8 (2)
O1^i—Cu1—N1—C6	−9.18 (13)	C2—N1—C6—C5	−2.5 (2)
Cu1—O1—C1—C2	−16.42 (15)	Cu1—N1—C6—C5	174.24 (12)
C6—N1—C2—C3	2.5 (2)	C4—C5—C6—N1	0.8 (2)
Cu1—N1—C2—C3	−174.59 (11)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^ii	0.84 (1)	1.75 (1)	2.5567 (16)	159 (2)

Symmetry code: (ii) x+1, y, z.