Methanol(2-methyl-1H-imidazole-κN³)(pyridine-2,6-di­carboxyl­ato-κ³N,O,O′)copper(II)

In the title compound, [Cu(C₇H₃NO₄)(C₄H₆N₂)(CH₄O)], the Cu atom lies in the centre of an N₂O₂ square plane, and the methanol mol­ecule is apically coordinated. The coordination geometry is best described as distorted square-pyramidal. There are intermolecular hydrogen bonds in the crystal structure, which mediate the formation of layers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.088
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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Computing details

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

Methanol(2-methyl-1H-imidazole-κ³)(pyridine-2,6-dicarboxylato- κ³N,O,O')copper(II)

Crystal data

[Cu(C7H3NO4)(C4H6N2)(CH4O)]	F(000) = 700
Mr = 342.79	Dx = 1.706 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3156 reflections
a = 8.5226 (10) Å	θ = 2.3–27.4°
b = 12.2353 (15) Å	µ = 1.66 mm^−1
c = 13.2586 (16) Å	T = 293 K
β = 105.095 (2)°	Prism, blue
V = 1334.9 (3) Å^3	0.30 × 0.28 × 0.14 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2619 independent reflections
Radiation source: sealed tube	2242 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→9
Tmin = 0.61, Tmax = 0.79	k = −15→15
7005 measured reflections	l = −16→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
2619 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.33 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 5.6245 (0.0046) x - 4.8863 (0.0073) y + 10.4250 (0.0060) z = 1.1941 (0.0043)

* -0.0376 (0.0009) O1 * -0.0369 (0.0009) O3 * 0.0953 (0.0011) N1 * 0.0805 (0.0008) N2 * -0.1013 (0.0008) Cu1

Rms deviation of fitted atoms = 0.0756

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
C1	0.3481 (3)	0.31749 (18)	0.46516 (19)	0.0281 (5)
C2	0.4727 (3)	0.3223 (2)	0.5545 (2)	0.0328 (6)
H2	0.5483	0.2660	0.5719	0.039*
C3	0.4831 (3)	0.4127 (2)	0.6181 (2)	0.0360 (6)
H3	0.5659	0.4173	0.6795	0.043*
C4	0.3717 (3)	0.4964 (2)	0.59119 (18)	0.0321 (6)
H4	0.3780	0.5574	0.6338	0.039*
C5	0.2509 (3)	0.48725 (18)	0.49980 (18)	0.0262 (5)
C6	0.3091 (3)	0.22676 (19)	0.3847 (2)	0.0326 (6)
C7	0.1206 (3)	0.5698 (2)	0.45100 (19)	0.0307 (5)
C8	−0.1959 (3)	0.4206 (2)	0.1265 (2)	0.0366 (6)
H8	−0.1460	0.4824	0.1082	0.044*
C9	−0.3343 (3)	0.3763 (2)	0.0697 (2)	0.0426 (7)
H9	−0.3982	0.4011	0.0059	0.051*
C10	−0.2429 (3)	0.2792 (2)	0.2126 (2)	0.0346 (6)
C11	−0.2323 (4)	0.1940 (2)	0.2919 (2)	0.0489 (7)
H11A	−0.1214	0.1709	0.3175	0.073*
H11B	−0.2982	0.1327	0.2615	0.073*
H11C	−0.2704	0.2225	0.3487	0.073*
C12	0.2873 (4)	0.4145 (3)	0.1496 (3)	0.0620 (9)
H12A	0.3292	0.3461	0.1808	0.093*
H12B	0.3761	0.4614	0.1462	0.093*
H12C	0.2202	0.4017	0.0803	0.093*
Cu1	0.06419 (3)	0.38541 (2)	0.32010 (2)	0.02989 (13)
N1	0.2420 (2)	0.39871 (15)	0.44114 (15)	0.0257 (4)
N2	−0.1389 (2)	0.36036 (17)	0.21622 (16)	0.0320 (5)
N3	−0.3625 (2)	0.28784 (19)	0.12409 (17)	0.0395 (5)
H3A	−0.4439	0.2442	0.1050	0.047*
O1	0.01611 (19)	0.53465 (14)	0.37023 (13)	0.0340 (4)
O2	0.1185 (2)	0.65842 (15)	0.49144 (15)	0.0462 (5)
O3	0.1741 (2)	0.23824 (14)	0.31662 (14)	0.0389 (4)
O4	0.4055 (2)	0.15145 (15)	0.39032 (16)	0.0448 (5)
O5	0.1947 (2)	0.46435 (15)	0.21000 (15)	0.0433 (5)
H5D	0.1534	0.5238	0.1819	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0262 (12)	0.0221 (12)	0.0362 (13)	−0.0017 (10)	0.0085 (10)	0.0033 (10)
C2	0.0261 (13)	0.0297 (13)	0.0402 (14)	0.0017 (10)	0.0042 (11)	0.0064 (11)
C3	0.0311 (13)	0.0417 (15)	0.0296 (14)	−0.0050 (11)	−0.0018 (10)	0.0009 (11)
C4	0.0330 (13)	0.0305 (13)	0.0303 (13)	−0.0030 (11)	0.0036 (10)	−0.0054 (10)
C5	0.0255 (12)	0.0249 (12)	0.0278 (12)	−0.0034 (10)	0.0062 (9)	−0.0004 (10)
C6	0.0376 (14)	0.0234 (12)	0.0381 (14)	−0.0021 (11)	0.0119 (11)	0.0001 (11)
C7	0.0288 (13)	0.0299 (13)	0.0320 (13)	0.0019 (11)	0.0057 (10)	0.0006 (11)
C8	0.0345 (14)	0.0371 (14)	0.0334 (15)	−0.0003 (12)	0.0003 (11)	−0.0021 (11)
C9	0.0387 (15)	0.0472 (17)	0.0373 (16)	0.0069 (13)	0.0016 (12)	−0.0028 (13)
C10	0.0310 (13)	0.0376 (14)	0.0356 (14)	−0.0047 (11)	0.0092 (11)	−0.0110 (11)
C11	0.0535 (18)	0.0466 (17)	0.0464 (17)	−0.0172 (14)	0.0129 (14)	−0.0056 (14)
C12	0.069 (2)	0.057 (2)	0.073 (2)	−0.0021 (18)	0.043 (2)	0.0006 (18)
Cu1	0.02757 (19)	0.02679 (19)	0.0304 (2)	−0.00199 (12)	−0.00122 (13)	−0.00311 (12)
N1	0.0230 (10)	0.0243 (10)	0.0281 (11)	−0.0019 (8)	0.0033 (8)	0.0016 (8)
N2	0.0264 (11)	0.0331 (11)	0.0329 (12)	−0.0042 (9)	0.0013 (9)	−0.0067 (9)
N3	0.0241 (11)	0.0475 (14)	0.0431 (13)	−0.0081 (10)	0.0020 (9)	−0.0156 (11)
O1	0.0284 (9)	0.0313 (9)	0.0365 (10)	0.0054 (7)	−0.0018 (8)	−0.0018 (8)
O2	0.0451 (11)	0.0310 (10)	0.0528 (12)	0.0096 (9)	−0.0045 (9)	−0.0115 (9)
O3	0.0405 (10)	0.0283 (9)	0.0416 (11)	0.0008 (8)	−0.0003 (8)	−0.0075 (8)
O4	0.0441 (11)	0.0331 (10)	0.0547 (13)	0.0085 (9)	0.0086 (9)	−0.0086 (9)
O5	0.0445 (11)	0.0405 (10)	0.0474 (11)	0.0033 (9)	0.0166 (9)	0.0108 (9)

Geometric parameters (Å, º)

C1—N1	1.325 (3)	C9—H9	0.9300
C1—C2	1.371 (3)	C10—N2	1.323 (3)
C1—C6	1.515 (3)	C10—N3	1.342 (3)
C2—C3	1.380 (4)	C10—C11	1.468 (4)
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.378 (3)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.375 (3)	C12—O5	1.403 (3)
C4—H4	0.9300	C12—H12A	0.9600
C5—N1	1.324 (3)	C12—H12B	0.9600
C5—C7	1.516 (3)	C12—H12C	0.9600
C6—O4	1.224 (3)	Cu1—N1	1.906 (2)
C6—O3	1.271 (3)	Cu1—N2	1.935 (2)
C7—O2	1.212 (3)	Cu1—O1	2.0213 (17)
C7—O1	1.276 (3)	Cu1—O3	2.0359 (17)
C8—C9	1.338 (4)	Cu1—O5	2.2685 (17)
C8—N2	1.376 (3)	N3—H3A	0.8600
C8—H8	0.9300	O5—H5D	0.8501
C9—N3	1.356 (4)
N1—C1—C2	120.1 (2)	C10—C11—H11C	109.5
N1—C1—C6	111.7 (2)	H11A—C11—H11C	109.5
C2—C1—C6	128.2 (2)	H11B—C11—H11C	109.5
C1—C2—C3	118.3 (2)	O5—C12—H12A	109.5
C1—C2—H2	120.8	O5—C12—H12B	109.5
C3—C2—H2	120.8	H12A—C12—H12B	109.5
C4—C3—C2	120.5 (2)	O5—C12—H12C	109.5
C4—C3—H3	119.8	H12A—C12—H12C	109.5
C2—C3—H3	119.8	H12B—C12—H12C	109.5
C5—C4—C3	118.4 (2)	N1—Cu1—N2	168.68 (8)
C5—C4—H4	120.8	N1—Cu1—O1	80.26 (7)
C3—C4—H4	120.8	N2—Cu1—O1	99.02 (8)
N1—C5—C4	119.9 (2)	N1—Cu1—O3	79.91 (7)
N1—C5—C7	111.8 (2)	N2—Cu1—O3	100.10 (8)
C4—C5—C7	128.3 (2)	O1—Cu1—O3	160.11 (7)
O4—C6—O3	126.5 (2)	N1—Cu1—O5	95.16 (7)
O4—C6—C1	119.2 (2)	N2—Cu1—O5	96.14 (8)
O3—C6—C1	114.3 (2)	O1—Cu1—O5	90.13 (7)
O2—C7—O1	125.8 (2)	O3—Cu1—O5	93.23 (7)
O2—C7—C5	120.1 (2)	C5—N1—C1	122.8 (2)
O1—C7—C5	114.0 (2)	C5—N1—Cu1	118.41 (16)
C9—C8—N2	109.3 (2)	C1—N1—Cu1	118.78 (16)
C9—C8—H8	125.4	C10—N2—C8	106.7 (2)
N2—C8—H8	125.4	C10—N2—Cu1	127.69 (18)
C8—C9—N3	106.0 (3)	C8—N2—Cu1	125.39 (17)
C8—C9—H9	127.0	C10—N3—C9	109.2 (2)
N3—C9—H9	127.0	C10—N3—H3A	125.4
N2—C10—N3	108.8 (2)	C9—N3—H3A	125.4
N2—C10—C11	126.2 (2)	C7—O1—Cu1	115.06 (15)
N3—C10—C11	125.0 (2)	C6—O3—Cu1	114.73 (15)
C10—C11—H11A	109.5	C12—O5—Cu1	128.73 (18)
C10—C11—H11B	109.5	C12—O5—H5D	110.6
H11A—C11—H11B	109.5	Cu1—O5—H5D	115.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2^i	0.86	1.99	2.806 (3)	158
O5—H5D···O4^ii	0.85	1.83	2.673 (3)	170

Symmetry codes: (i) −x−1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2.