Aqua­tetrakis(2-methyl­pyrazine-κN)(nitrato-κO)copper(II) nitrate

Otieno, T.; Pinkston, A.T.; Johnson, N.C.; Parkin, S.

doi:10.1107/S1600536802010048

Aquatetrakis(2-methylpyrazine-κN)(nitrato-κO)copper(II) nitrate

T. Otieno, A. T. Pinkston, N. C. Johnson and S. Parkin

The copper(II) ion in the title compound, [Cu(NO₃)(mepyz)₄(H₂O)]NO₃, where mepyz is 2-methylpyrazine (C₅H₆N₂), has a distorted octahedral geometry with four N atoms of the methylpyrazine ligands in the equatorial positions and two O atoms from water and semi-coordinated nitrate moieties in the axial sites.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010048/wn6100sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010048/wn6100Isup2.hkl Contains datablock I

CCDC reference: 189863

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.049
wR factor = 0.129
Data-to-parameter ratio = 12.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      3
                   N5  -CU  -N1  -C4   -179.00100.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #      8
                   N5  -CU  -N1  -C1     -5.00  4.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     21
                   N7  -CU  -N3  -C9    -41.50  0.90   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     26
                   N7  -CU  -N3  -C6    137.40  0.70   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     43
                   N1  -CU  -N5  -C14   103.00  4.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     48
                   N1  -CU  -N5  -C11   -77.00  4.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     61
                   N3  -CU  -N7  -C19   156.10  0.70   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     66
                   N3  -CU  -N7  -C16   -24.20  0.90   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     89
                   O1  -CU  -O1N2-N1N2 -159.30  0.70   1.555   1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 9 Alert Level C = Please check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97 and local procedures.

Aquatetrakis(methylpyrazine-N)(nitrato-O)copper(II) nitrate top

Crystal data top

[Cu(NO₃)(C₅H₆N₂)₄(H₂O)]NO₃	Z = 2
M_r = 582.05	F(000) = 602
Triclinic, P1	D_x = 1.518 Mg m⁻³
a = 8.448 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.309 (1) Å	Cell parameters from 33129 reflections
c = 12.841 (1) Å	θ = 1.0–27.5°
α = 88.562 (10)°	µ = 0.92 mm⁻¹
β = 72.938 (10)°	T = 173 K
γ = 86.242 (10)°	Irregular slab, blue
V = 1273.8 (2) Å³	0.30 × 0.28 × 0.12 mm

Data collection top

Nonius KappaCCD diffractometer	4496 independent reflections
Radiation source: fine-focus sealed tube	4037 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 18 pixels mm^-1	θ_max = 25.0°, θ_min = 1.7°
ω scans at fixed χ = 55°	h = −9→10
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −14→14
T_min = 0.770, T_max = 0.898	l = −15→15
4496 measured reflections

Refinement top

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0643P)² + 1.3703P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.009
4496 reflections	Δρ_max = 1.25 e Å⁻³
366 parameters	Δρ_min = −0.47 e Å⁻³
21 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (17)

Special details top

Experimental. These crystals were non-merohedrally twinned. As a result, there are a lot of reflections for which F_o is significantly larger than Fc. Also the difference map is quite lumpy. Nevertheless, refinement was quite straightforward.

Cu(NO₃)₂·2.5H₂O and 2-methylpyrazine (mepyz) were purchased from commercial sources and used as received. 2-Methylpyrazine (4.70 ml, 4.84 g, 51.4 mmol) was added to a 3 ml aqueous solution of Cu(NO₃)₂·2.5H₂O (1.00 g, 4.30 mmol). The reaction vessel was covered with parafilm in which pinholes were made to allow for slow evaporation of the solvent. Dark blue crystals of [Cu(mepyz)₄(H₂O)(NO₃)](NO₃) formed within a few days. These were isolated by decantation, mopped dry using filter paper and air-dried for less than 5 minutes. Analysis found: C, 40.79; H, 4.37; N, 23.79. C₂₀H₂₆CuN₁₀O₇ requires: C, 41.27; H, 4.50; N, 24.06%. Washing the product or leaving it in the open for prolonged periods of time leads to decomposition via loss of mepyz ligands.

Reaction of copper(II) nitrate and a large excess of 2-methylpyrazine using ethanol containing 10% (v/v) 2,2-dimethoxypropane as the solvent leads to the precipitation of the solvated tetrakis(2-methylpyrazine) compound, Cu(mepyz)₄(NO₃)₂·EtOH. The blue solid was isolated by vacuum filtration and dried under vacuum for about 5 minutes. Analysis found: C, 43.09; H, 5.36; N, 22.44. C₂₂H₃₀CuN₁₀O₇ requires: C, 43.31; H, 4.96; N, 22.96%.

Cu(mepyz)₄(NO₃)₂ (either as the water or ethanol solvate) readily looses some 2-methylpyrazine ligands and is converted to Cu(mepyz)(NO₃)₂ when left in open containers, whether exposed to air or an inert atmosphere. This transformation is accompanied by a color change from blue to a purple blue (periwinkle) and its completion was confirmed by elemental analysis. Analysis found: C, 21.16; H, 2.12; N, 19.69. C₅H₆CuN₄O₆ requires: C, 21.32; H, 2.15; N, 19.89%.

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 > 2sigma(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.

TwinRotMat in Ton Spek's Platon gives the following as the most likely twin law. Refinement based on the HKLF 5 format datafile produced by this program (PLATON: Spek, A.L. (1990), Acta Cryst. A46, C-34) is.

2-Rotation about (1 2 -3) [9 5 -9] Fit: 5(59) Det (-0.608 0.217 -0.391) (h1) (h2) Alpha () [] = ( 0.785 -0.565 -0.782) * (k1) = (k2) = 1.000 (-1.177 -0.652 0.173) (l1) = (l2) 0.11 Deg.

The largest difference map feature (1.25eA^{-3) is quite close to the
major component of the disordered methyl group C20. It is most
likely a consequence of the trade off between modelling of twinning
and/or modelling of disorder.}

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu	0.64420 (5)	0.25714 (3)	0.21942 (3)	0.02371 (17)
O1	0.4299 (3)	0.2666 (2)	0.1458 (2)	0.0324 (6)
H1O	0.3320	0.2757	0.1822	0.049*
H2O	0.4256	0.2579	0.0807	0.049*
N1	0.7949 (3)	0.1770 (2)	0.0869 (2)	0.0218 (6)
N2	0.9877 (4)	0.0816 (2)	−0.1072 (2)	0.0271 (6)
C1	0.9568 (4)	0.1952 (3)	0.0462 (3)	0.0245 (7)
H1	1.0066	0.2420	0.0836	0.029*
C2	1.0510 (4)	0.1464 (3)	−0.0495 (3)	0.0265 (7)
H2	1.1657	0.1593	−0.0754	0.032*
C3	0.8267 (4)	0.0643 (3)	−0.0666 (3)	0.0254 (7)
C4	0.7319 (4)	0.1101 (3)	0.0314 (3)	0.0248 (7)
H4	0.6190	0.0932	0.0597	0.030*
C5	0.7492 (5)	−0.0058 (3)	−0.1295 (3)	0.0394 (9)
H5A	0.8340	−0.0331	−0.1948	0.059*
H5B	0.6618	0.0372	−0.1508	0.059*
H5C	0.7011	−0.0673	−0.0839	0.059*
N3	0.7265 (3)	0.4003 (2)	0.1509 (2)	0.0224 (6)
N4	0.8493 (4)	0.5952 (2)	0.0561 (2)	0.0310 (7)
C6	0.7134 (4)	0.4327 (3)	0.0528 (3)	0.0273 (7)
H6	0.6617	0.3884	0.0143	0.033*
C7	0.7743 (4)	0.5296 (3)	0.0078 (3)	0.0297 (8)
H7	0.7621	0.5506	−0.0613	0.036*
C8	0.8621 (4)	0.5631 (3)	0.1538 (3)	0.0269 (7)
C9	0.7998 (4)	0.4670 (3)	0.2015 (3)	0.0245 (7)
H9	0.8089	0.4475	0.2717	0.029*
C10	0.9476 (6)	0.6344 (4)	0.2116 (3)	0.0456 (10)
H10A	1.0578	0.6490	0.1634	0.068*
H10B	0.9589	0.5973	0.2777	0.068*
H10C	0.8817	0.7034	0.2314	0.068*
N5	0.4991 (3)	0.3393 (2)	0.3525 (2)	0.0233 (6)
N6	0.2996 (4)	0.4526 (3)	0.5331 (2)	0.0324 (7)
C11	0.4967 (4)	0.3093 (3)	0.4540 (3)	0.0281 (7)
H11	0.5646	0.2480	0.4647	0.034*
C12	0.3976 (5)	0.3656 (3)	0.5427 (3)	0.0325 (8)
H12	0.3988	0.3420	0.6135	0.039*
C13	0.3022 (4)	0.4840 (3)	0.4321 (3)	0.0306 (8)
C14	0.4016 (4)	0.4266 (3)	0.3422 (3)	0.0261 (7)
H14	0.4002	0.4499	0.2713	0.031*
C15	0.1956 (5)	0.5827 (4)	0.4183 (3)	0.0452 (10)
H15A	0.0830	0.5615	0.4258	0.068*
H15B	0.2423	0.6147	0.3460	0.068*
H15C	0.1921	0.6363	0.4743	0.068*
N7	0.5889 (3)	0.1109 (2)	0.2939 (2)	0.0260 (6)
N8	0.5186 (5)	−0.0896 (3)	0.3983 (3)	0.0405 (8)
C16	0.7094 (5)	0.0393 (3)	0.3059 (3)	0.0345 (8)
H16	0.8220	0.0567	0.2774	0.041*
C17	0.6731 (5)	−0.0589 (3)	0.3587 (3)	0.0397 (9)
H17	0.753 (6)	−0.113 (4)	0.365 (4)	0.048*	0.734 (10)
C18	0.3985 (5)	−0.0201 (3)	0.3825 (3)	0.0368 (9)
H18	0.294 (11)	−0.050 (14)	0.408 (7)	0.044*	0.266 (10)
C19	0.4330 (4)	0.0802 (3)	0.3329 (3)	0.0308 (8)
H19	0.3440	0.1285	0.3263	0.037*
C20	0.2206 (9)	−0.0571 (7)	0.4210 (6)	0.064 (2)	0.734 (10)
H20A	0.2060	−0.1106	0.3699	0.096*	0.734 (10)
H20B	0.1422	0.0059	0.4242	0.096*	0.734 (10)
H20C	0.2001	−0.0903	0.4936	0.096*	0.734 (10)
C20'	0.8181 (17)	−0.1250 (12)	0.3812 (13)	0.039 (4)	0.266 (10)
H20D	0.7795	−0.1635	0.4509	0.059*	0.266 (10)
H20E	0.9036	−0.0761	0.3844	0.059*	0.266 (10)
H20F	0.8647	−0.1779	0.3228	0.059*	0.266 (10)
N1N1	0.4990 (5)	0.2680 (3)	−0.1419 (3)	0.0449 (9)
O1N1	0.4570 (5)	0.2531 (3)	−0.2235 (3)	0.0727 (11)
O2N1	0.5807 (5)	0.3479 (4)	−0.1380 (3)	0.0775 (12)
O3N1	0.4457 (4)	0.2086 (2)	−0.0598 (2)	0.0472 (7)
N1N2	1.0144 (4)	0.2613 (3)	0.3127 (3)	0.0345 (7)
O1N2	0.8652 (3)	0.2490 (2)	0.3258 (2)	0.0409 (7)
O2N2	1.0950 (3)	0.3149 (3)	0.2323 (2)	0.0471 (7)
O3N2	1.0849 (4)	0.2263 (4)	0.3778 (3)	0.0866 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0238 (2)	0.0231 (2)	0.0234 (2)	−0.00204 (17)	−0.00543 (17)	−0.00051 (16)
O1	0.0211 (12)	0.0475 (15)	0.0305 (13)	−0.0010 (11)	−0.0104 (10)	−0.0047 (11)
N1	0.0219 (14)	0.0204 (14)	0.0238 (14)	−0.0004 (11)	−0.0081 (11)	0.0014 (11)
N2	0.0295 (15)	0.0248 (15)	0.0266 (15)	0.0018 (12)	−0.0079 (12)	−0.0025 (12)
C1	0.0235 (17)	0.0215 (17)	0.0314 (18)	−0.0013 (13)	−0.0125 (14)	0.0019 (14)
C2	0.0219 (16)	0.0225 (17)	0.0344 (19)	−0.0016 (13)	−0.0071 (14)	0.0032 (14)
C3	0.0285 (18)	0.0207 (17)	0.0293 (17)	0.0031 (14)	−0.0132 (15)	−0.0005 (13)
C4	0.0194 (16)	0.0237 (17)	0.0329 (18)	−0.0009 (13)	−0.0103 (14)	0.0022 (14)
C5	0.041 (2)	0.039 (2)	0.044 (2)	0.0003 (18)	−0.0210 (18)	−0.0118 (18)
N3	0.0215 (14)	0.0246 (14)	0.0208 (13)	0.0011 (11)	−0.0060 (11)	−0.0005 (11)
N4	0.0352 (17)	0.0287 (16)	0.0295 (16)	−0.0023 (13)	−0.0104 (13)	0.0042 (12)
C6	0.0240 (17)	0.0331 (19)	0.0261 (17)	0.0006 (14)	−0.0096 (14)	−0.0014 (14)
C7	0.0303 (18)	0.0330 (19)	0.0271 (17)	0.0034 (15)	−0.0119 (15)	0.0063 (15)
C8	0.0264 (17)	0.0267 (18)	0.0273 (18)	−0.0005 (14)	−0.0075 (14)	−0.0016 (14)
C9	0.0244 (16)	0.0266 (18)	0.0231 (16)	0.0032 (14)	−0.0089 (13)	−0.0007 (13)
C10	0.059 (3)	0.045 (2)	0.040 (2)	−0.023 (2)	−0.021 (2)	0.0070 (18)
N5	0.0213 (14)	0.0249 (14)	0.0248 (14)	−0.0043 (11)	−0.0080 (11)	0.0010 (11)
N6	0.0320 (16)	0.0369 (17)	0.0264 (15)	0.0014 (14)	−0.0061 (13)	−0.0015 (13)
C11	0.0317 (18)	0.0256 (18)	0.0277 (18)	−0.0039 (15)	−0.0095 (15)	0.0035 (14)
C12	0.037 (2)	0.035 (2)	0.0249 (17)	−0.0042 (16)	−0.0081 (15)	0.0043 (15)
C13	0.0248 (18)	0.037 (2)	0.0312 (19)	0.0016 (15)	−0.0107 (15)	−0.0030 (15)
C14	0.0233 (17)	0.0330 (19)	0.0248 (17)	−0.0002 (15)	−0.0118 (14)	0.0014 (14)
C15	0.040 (2)	0.055 (3)	0.039 (2)	0.022 (2)	−0.0137 (18)	−0.0047 (19)
N7	0.0276 (15)	0.0262 (15)	0.0238 (14)	−0.0019 (12)	−0.0068 (12)	−0.0031 (11)
N8	0.061 (2)	0.0303 (17)	0.0319 (17)	−0.0087 (16)	−0.0147 (16)	0.0032 (13)
C16	0.033 (2)	0.033 (2)	0.0340 (19)	0.0028 (16)	−0.0050 (15)	0.0002 (15)
C17	0.052 (3)	0.029 (2)	0.034 (2)	0.0074 (18)	−0.0073 (18)	0.0022 (16)
C18	0.045 (2)	0.042 (2)	0.0285 (19)	−0.0175 (19)	−0.0157 (17)	0.0065 (16)
C19	0.0325 (19)	0.036 (2)	0.0275 (18)	−0.0083 (16)	−0.0134 (15)	0.0023 (15)
C20	0.067 (5)	0.074 (4)	0.063 (4)	−0.039 (4)	−0.033 (3)	0.027 (3)
C20'	0.037 (7)	0.029 (7)	0.047 (7)	0.007 (5)	−0.007 (6)	0.013 (6)
N1N1	0.049 (2)	0.053 (2)	0.039 (2)	0.0028 (18)	−0.0240 (17)	−0.0083 (17)
O1N1	0.103 (3)	0.087 (3)	0.0427 (18)	−0.009 (2)	−0.0433 (19)	−0.0041 (17)
O2N1	0.074 (2)	0.110 (3)	0.055 (2)	−0.043 (2)	−0.0192 (18)	−0.010 (2)
O3N1	0.0506 (18)	0.0524 (18)	0.0418 (16)	0.0057 (14)	−0.0208 (14)	0.0040 (14)
N1N2	0.0280 (17)	0.0410 (19)	0.0348 (17)	0.0085 (14)	−0.0117 (14)	−0.0030 (14)
O1N2	0.0249 (14)	0.0478 (17)	0.0517 (17)	−0.0040 (12)	−0.0144 (12)	0.0096 (13)
O2N2	0.0294 (14)	0.0609 (19)	0.0489 (17)	−0.0021 (13)	−0.0091 (13)	0.0082 (14)
O3N2	0.0431 (19)	0.148 (4)	0.067 (2)	0.019 (2)	−0.0215 (18)	0.042 (2)

Geometric parameters (Å, º) top

Cu—N3	2.021 (3)	N6—C13	1.338 (5)
Cu—N7	2.033 (3)	C11—C12	1.372 (5)
Cu—N1	2.034 (3)	C11—H11	0.9500
Cu—N5	2.035 (3)	C12—H12	0.9500
Cu—O1	2.271 (2)	C13—C14	1.390 (5)
Cu—O1N2	2.613 (3)	C13—C15	1.502 (5)
O1—H1O	0.8240	C14—H14	0.9500
O1—H2O	0.8560	C15—H15A	0.9800
N1—C4	1.335 (4)	C15—H15B	0.9800
N1—C1	1.344 (4)	C15—H15C	0.9800
N2—C3	1.336 (4)	N7—C19	1.341 (4)
N2—C2	1.338 (4)	N7—C16	1.343 (5)
C1—C2	1.380 (5)	N8—C17	1.331 (5)
C1—H1	0.9500	N8—C18	1.342 (5)
C2—H2	0.9500	C16—C17	1.378 (5)
C3—C4	1.389 (5)	C16—H16	0.9500
C3—C5	1.497 (5)	C17—C20'	1.520 (12)
C4—H4	0.9500	C17—H17	0.94 (2)
C5—H5A	0.9800	C18—C19	1.383 (5)
C5—H5B	0.9800	C18—C20	1.534 (7)
C5—H5C	0.9800	C18—H18	0.95 (2)
N3—C9	1.345 (4)	C19—H19	0.9500
N3—C6	1.346 (4)	C20—H18	0.60 (6)
N4—C7	1.328 (5)	C20—H20A	0.9800
N4—C8	1.339 (4)	C20—H20B	0.9800
C6—C7	1.376 (5)	C20—H20C	0.9800
C6—H6	0.9500	C20'—H17	0.65 (4)
C7—H7	0.9500	C20'—H20D	0.9800
C8—C9	1.382 (5)	C20'—H20E	0.9800
C8—C10	1.508 (5)	C20'—H20F	0.9800
C9—H9	0.9500	N1N1—O1N1	1.223 (4)
C10—H10A	0.9800	N1N1—O2N1	1.248 (5)
C10—H10B	0.9800	N1N1—O3N1	1.255 (4)
C10—H10C	0.9800	N1N2—O3N2	1.217 (4)
N5—C14	1.338 (4)	N1N2—O1N2	1.240 (4)
N5—C11	1.340 (4)	N1N2—O2N2	1.256 (4)
N6—C12	1.336 (5)

N3—Cu—N7	172.61 (11)	C11—N5—Cu	122.0 (2)
N3—Cu—N1	89.75 (10)	C12—N6—C13	117.1 (3)
N7—Cu—N1	88.95 (10)	N5—C11—C12	121.1 (3)
N3—Cu—N5	89.30 (10)	N5—C11—H11	119.5
N7—Cu—N5	91.82 (11)	C12—C11—H11	119.5
N1—Cu—N5	178.36 (10)	N6—C12—C11	122.3 (3)
N3—Cu—O1	92.44 (10)	N6—C12—H12	118.8
N7—Cu—O1	94.86 (11)	C11—C12—H12	118.8
N1—Cu—O1	91.42 (10)	N6—C13—C14	120.6 (3)
N5—Cu—O1	89.96 (10)	N6—C13—C15	118.5 (3)
N3—Cu—O1N2	90.10 (10)	C14—C13—C15	120.9 (3)
N7—Cu—O1N2	82.76 (10)	N5—C14—C13	121.9 (3)
N1—Cu—O1N2	94.63 (10)	N5—C14—H14	119.1
N5—Cu—O1N2	84.03 (10)	C13—C14—H14	119.1
O1—Cu—O1N2	173.45 (9)	C13—C15—H15A	109.5
Cu—O1—H1O	123.3	C13—C15—H15B	109.5
Cu—O1—H2O	132.3	H15A—C15—H15B	109.5
H1O—O1—H2O	104.2	C13—C15—H15C	109.5
C4—N1—C1	117.2 (3)	H15A—C15—H15C	109.5
C4—N1—Cu	120.2 (2)	H15B—C15—H15C	109.5
C1—N1—Cu	122.4 (2)	C19—N7—C16	116.4 (3)
C3—N2—C2	116.5 (3)	C19—N7—Cu	122.7 (2)
N1—C1—C2	120.4 (3)	C16—N7—Cu	120.9 (2)
N1—C1—H1	119.8	C17—N8—C18	116.2 (3)
C2—C1—H1	119.8	N7—C16—C17	121.3 (4)
N2—C2—C1	122.8 (3)	N7—C16—H16	119.3
N2—C2—H2	118.6	C17—C16—H16	119.3
C1—C2—H2	118.6	N8—C17—C16	122.5 (4)
N2—C3—C4	121.2 (3)	N8—C17—C20'	121.1 (7)
N2—C3—C5	118.5 (3)	C16—C17—C20'	116.0 (7)
C4—C3—C5	120.2 (3)	N8—C17—H17	113 (4)
N1—C4—C3	121.8 (3)	C16—C17—H17	124 (4)
N1—C4—H4	119.1	C20'—C17—H17	14 (4)
C3—C4—H4	119.1	N8—C18—C19	121.7 (3)
C3—C5—H5A	109.5	N8—C18—C20	117.1 (4)
C3—C5—H5B	109.5	C19—C18—C20	121.2 (4)
H5A—C5—H5B	109.5	N8—C18—H18	111 (10)
C3—C5—H5C	109.5	C19—C18—H18	127 (10)
H5A—C5—H5C	109.5	C20—C18—H18	6 (10)
H5B—C5—H5C	109.5	N7—C19—C18	121.7 (3)
C9—N3—C6	116.9 (3)	N7—C19—H19	119.2
C9—N3—Cu	121.0 (2)	C18—C19—H19	119.2
C6—N3—Cu	122.1 (2)	C18—C20—H18	10 (10)
C7—N4—C8	116.4 (3)	C18—C20—H20A	109.5
N3—C6—C7	120.4 (3)	C18—C20—H20B	109.5
N3—C6—H6	119.8	C18—C20—H20C	109.5
C7—C6—H6	119.8	C17—C20'—H17	20 (5)
N4—C7—C6	123.2 (3)	C17—C20'—H20D	109.5
N4—C7—H7	118.4	H17—C20'—H20D	106.1
C6—C7—H7	118.4	C17—C20'—H20E	109.5
N4—C8—C9	121.5 (3)	H17—C20'—H20E	127.5
N4—C8—C10	118.4 (3)	H20D—C20'—H20E	109.5
C9—C8—C10	120.1 (3)	C17—C20'—H20F	109.5
N3—C9—C8	121.6 (3)	H17—C20'—H20F	93.1
N3—C9—H9	119.2	H20D—C20'—H20F	109.5
C8—C9—H9	119.2	H20E—C20'—H20F	109.5
C8—C10—H10A	109.5	O1N1—N1N1—O2N1	119.5 (4)
C8—C10—H10B	109.5	O1N1—N1N1—O3N1	119.1 (4)
H10A—C10—H10B	109.5	O2N1—N1N1—O3N1	121.0 (3)
C8—C10—H10C	109.5	O3N2—N1N2—O1N2	122.1 (3)
H10A—C10—H10C	109.5	O3N2—N1N2—O2N2	118.2 (3)
H10B—C10—H10C	109.5	O1N2—N1N2—O2N2	119.7 (3)
C14—N5—C11	117.0 (3)	N1N2—O1N2—Cu	141.5 (2)
C14—N5—Cu	121.0 (2)

N3—Cu—N1—C4	−124.6 (2)	N3—Cu—N5—C11	−131.2 (3)
N7—Cu—N1—C4	62.7 (2)	N7—Cu—N5—C11	41.5 (3)
N5—Cu—N1—C4	−179 (100)	N1—Cu—N5—C11	−77 (4)
O1—Cu—N1—C4	−32.1 (2)	O1—Cu—N5—C11	136.4 (3)
O1N2—Cu—N1—C4	145.4 (2)	O1N2—Cu—N5—C11	−41.0 (3)
N3—Cu—N1—C1	49.9 (3)	C14—N5—C11—C12	0.3 (5)
N7—Cu—N1—C1	−122.8 (3)	Cu—N5—C11—C12	−179.8 (3)
N5—Cu—N1—C1	−5 (4)	C13—N6—C12—C11	−0.5 (5)
O1—Cu—N1—C1	142.3 (3)	N5—C11—C12—N6	−0.1 (5)
O1N2—Cu—N1—C1	−40.2 (3)	C12—N6—C13—C14	1.0 (5)
C4—N1—C1—C2	0.5 (5)	C12—N6—C13—C15	−179.0 (3)
Cu—N1—C1—C2	−174.2 (2)	C11—N5—C14—C13	0.2 (5)
C3—N2—C2—C1	−1.2 (5)	Cu—N5—C14—C13	−179.7 (2)
N1—C1—C2—N2	1.5 (5)	N6—C13—C14—N5	−0.8 (5)
C2—N2—C3—C4	−1.0 (5)	C15—C13—C14—N5	179.1 (3)
C2—N2—C3—C5	178.8 (3)	N3—Cu—N7—C19	156.1 (7)
C1—N1—C4—C3	−2.7 (5)	N1—Cu—N7—C19	−124.0 (3)
Cu—N1—C4—C3	172.1 (2)	N5—Cu—N7—C19	57.5 (3)
N2—C3—C4—N1	3.1 (5)	O1—Cu—N7—C19	−32.6 (3)
C5—C3—C4—N1	−176.7 (3)	O1N2—Cu—N7—C19	141.2 (3)
N7—Cu—N3—C9	−41.5 (9)	N3—Cu—N7—C16	−24.2 (9)
N1—Cu—N3—C9	−121.4 (2)	N1—Cu—N7—C16	55.7 (3)
N5—Cu—N3—C9	57.3 (2)	N5—Cu—N7—C16	−122.8 (3)
O1—Cu—N3—C9	147.2 (2)	O1—Cu—N7—C16	147.1 (3)
O1N2—Cu—N3—C9	−26.7 (2)	O1N2—Cu—N7—C16	−39.1 (3)
N7—Cu—N3—C6	137.4 (7)	C19—N7—C16—C17	−2.0 (5)
N1—Cu—N3—C6	57.5 (2)	Cu—N7—C16—C17	178.3 (3)
N5—Cu—N3—C6	−123.8 (3)	C18—N8—C17—C16	1.0 (5)
O1—Cu—N3—C6	−33.9 (2)	C18—N8—C17—C20'	173.7 (8)
O1N2—Cu—N3—C6	152.2 (2)	N7—C16—C17—N8	1.6 (6)
C9—N3—C6—C7	0.4 (5)	N7—C16—C17—C20'	−171.4 (7)
Cu—N3—C6—C7	−178.5 (2)	C17—N8—C18—C19	−3.2 (5)
C8—N4—C7—C6	−0.8 (5)	C17—N8—C18—C20	176.2 (4)
N3—C6—C7—N4	0.7 (5)	C16—N7—C19—C18	−0.2 (5)
C7—N4—C8—C9	−0.2 (5)	Cu—N7—C19—C18	179.5 (3)
C7—N4—C8—C10	179.5 (3)	N8—C18—C19—N7	2.9 (5)
C6—N3—C9—C8	−1.4 (4)	C20—C18—C19—N7	−176.5 (4)
Cu—N3—C9—C8	177.6 (2)	O3N2—N1N2—O1N2—Cu	−162.7 (4)
N4—C8—C9—N3	1.4 (5)	O2N2—N1N2—O1N2—Cu	20.2 (6)
C10—C8—C9—N3	−178.4 (3)	N3—Cu—O1N2—N1N2	−46.5 (4)
N3—Cu—N5—C14	48.7 (3)	N7—Cu—O1N2—N1N2	131.6 (4)
N7—Cu—N5—C14	−138.6 (2)	N1—Cu—O1N2—N1N2	43.3 (4)
N1—Cu—N5—C14	103 (4)	N5—Cu—O1N2—N1N2	−135.7 (4)
O1—Cu—N5—C14	−43.7 (2)	O1—Cu—O1N2—N1N2	−159.3 (7)
O1N2—Cu—N5—C14	138.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2N2ⁱ	0.82	1.94	2.746 (5)	164
O1—H2O···O3N1	0.86	1.88	2.719 (5)	167

Symmetry code: (i) x−1, y, z.

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Aqua­tetrakis(2-methyl­pyrazine-κN)(nitrato-κO)copper(II) nitrate

Supporting information

Key indicators

checkCIF results

Aquatetrakis(2-methylpyrazine-κN)(nitrato-κO)copper(II) nitrate