Cobalt(II), nickel(II) and copper(II) complexes of iso­quinoline-3-carbox­ylate

The crystal structures of the title complexes, namely trans-bis­(iso­quinoline-3-carboxyl­ato-[kappa]²N,O)­bis­(methanol-[kappa]O)cobalt(II), [Co(C₁₀H₆NO₂)₂(CH₃OH)₂], and the corresponding nickel(II) and copper(II) complexes, [Ni(C₁₀H₆NO₂)₂(CH₃OH)₂] and [Cu(C₁₀H₆NO₂)₂(CH₃OH)₂], are isomorphous and contain metal ions at centres of inversion. The three compounds have the same distorted octahedral coordination geometry, and each metal ion is bonded by two quinoline N atoms, two carboxyl­ate O atoms and two methanol O atoms. Two iso­quinoline-3-carboxyl­ate ligands lie in trans positions, forming the equatorial plane, and the two methanol ligands occupy the axial positions. The complex mol­ecules are linked together by O-H...O hydrogen bonds between the methanol ligands and neighbouring carboxyl­ate groups.

S1. Comment

Transition metal ions are well known to have many important biological functions, mainly as the cofactors of many metalloenzymes. Their complexes have remarkable antimicrobial or fungicidal activity (Okide et al., 2000; Patel et al., 1999), or have redox activity and act as catalysts for metal-induced toxicity or carcinogenesis through processes which are interpreted as Fenton-type reactions (Kasprzak, 2002).

On the other hand, isoquinoline-3-carboxylic acid is a potent non-peptidyl inhibitor of the insulin-like growth factor binding proteins (Zhu et al., 2003). Its transition metal (mainly Fe) complexes act as oxidative catalysts in alkane oxidations (Shul'pin, 2002). In a previous paper, the crystal structure of the Fe^II complex of isoquinoline-3-carboxylate has been reported (Okabe & Muranishi, 2003c). Here, we report the structures of the corresponding Co^II, Ni^II & Cu^II complexes, (I), (II) and (III), respectively, and compare their structural features. \sch

The structure of (I) is shown in Fig. 1. The structures of (I), (II) and (III) are isomorphous with the aforementioned Fe^II analogue and have the same distorted octahedral coordination geometries, with the metal ion at a centre of inversion. The two bidentate ligands lie trans to one another. They are coordinated to the central metal ion, through the isoquinoline N atoms and the carboxylate O atoms, to form a five-membered ring in the equatorial plane. Two O atoms of the methanol ligands complete the octahedron at the axial positions.

As shown in Table 1, the M—N coordination bond distances decrease in the order Fe^II > (I) > (II) > (III). The reverse of this order coincides well with the Irving-Williams series, which indicates the general stability sequence of octahedral metal complexes in the order Fe < Co < Ni < Cu. The axial coordination bond distances of the Cu^II complex, (III), are noticeably longer than those in (I) and (II), as well as in the Fe^II complex. This may be explained by a strong Jahn-Teller effect in (III).

In the heterocyclic ring, the N1—C1 and N1—C9 bonds on both sides of the ring N atom and the C1—C2 bond of (I), (II) and (III) are shorter than the others in the same pyridine ring, C2—C3, C3—C8 and C8—C9 (Table 1). This indicates the delocalization of the π electron over these three bonds, which have double-bond character. This type of delocalization of π electrons is also present in the Fe^II complex, and it may be a general characteristic of the transition metal complexes of isoquinoline-3-carboxylate. Only the bonds on either side of the N atom have double-bond character in the metal complexes of analogous compounds, such as isoquinoline-1-carboxylate complexes with Fe^II (Muranishi & Okabe, 2003), Co^II and Ni^II (Okabe & Muranishi, 2002), and Zn^II (Okabe & Muranishi, 2003b), and quinoline-2-carboxylate complexes with Fe^II (Okabe & Makino, 1998), Co^II (Okabe & Makino, 1999), Ni^II (Odoko et al., 2001) and Zn^II (Okabe & Muranishi, 2003a).

When the Co (or Ni or Fe)—N coordination bond distances for (I), (II) and analogous complexes of isoquinoline-1-carboxylate and quinoline-2-carboxylate are compared, they are found to decrease in the following order. For quinoline-2-carboxylate complexes with Co [2.226 (3)], Ni [2.182 (2)] or Fe [2.270 (1) Å], the M—N distances are longer than in (I), (II), (III) or Fe [2.167 (2) Å], which are in turn longer than those in isoquinoline-1-carboxylate complexes with Co [2.096 (2)], Ni [2.039 (3)], Cu [1.957 (3) and 1.969 (3)] or [Fe 2.153 (2) Å]. The penta-coordinate Cu^II complex of quinoline-2-carboxylate (Haendler, 1986) has been excluded from this discussion. This paragraph has been extensively reworded. Please check that the intended meaning has not been affected.

The Co (or Ni)—O bond distances in (I), (II) and analogous complexes are in almost the reverse order of the M—N distances, and decrease in the following order. For isoquinoline-1-carboxylate complexes with Co [2.055 (2)] or Ni [2.036 (2) Å], the M—O distances are longer than in (I) or (II), which are in turn longer than those in quinoline-2-carboxylate complexes with Co [2.027 (3)] or Ni [2.004 (2) Å]. The Fe—O distances decrease in the following order. For the isoquinoline-1-carboxylate complex, the Fe—O distance of 2.091 (2) Å is longer than in the quinoline-2-carboxylate complex [2.087 (1) Å], which is in turn longer than that in the isoquinoline-3-carboxylate complex [2.049 (2) Å]. The Cu—O distances also vary across a range of compounds. In (III), Cu—O is longer than in the isoquinoline-1-carboxylate complex [1.927 (3) and 1.928 (3) Å; Pardo et al., 1999]·This paragraph has been extensively reworded. Please check that the intended meaning has not been affected.

These data indicate that the same order of bond distances is present in the M—N distances of these complexes, but not in the M—O distances. These latter may be changed under the influence of the electronegativity of the carboxylate anion, although the same order for M—O is present in Co^II and Ni^II complexes.

The M—O bond distance is indicative of bond stability and may have an influence on the catalytic activity of isoquinoline-1- and −3-carboxylate complexes. For example, the Fe complex of isoquinoline-3-carboxylate, with a rather short M—O distance compared with the complex with isoquinoline-1-carboxylate, has a more effective catalytic activity in oxygen formation from cyclooctane in Gif oxidation (Shul'pin, 2002) The difference in double-bond character around the N atom of the heterocyclic ring may be one of reasons for the difference in M—N(or O) coordination bond distances between the above analogous complexes.

The hydrogen-bonding parameters of the Fe^II complex, (I), (II) and (III) are listed in Table 2. A l l structures are stabilized by a similar intermolecular O—H···O hydrogen-bonding pattern between methanol ligands and neighbouring carboxylate groups. The structures are also stabilized by a stacking interaction between the isoquinoline rings, at a mean distance of 3.358 (3) for (I), 3.362 (3) for (II) and 3.362 (3) Å for (III).

S2. Experimental

Orange plate crystals of (I) were obtained by slow evaporation of a methanol solution of a mixture of isoquinoline-3-carboxylic acid and CoCl₂·6H₂O (molar ratio 4:1) at room temperature. Light-blue Colourless below? plate crystals of (II) were obtained by slow evaporation of a methanol solution of a mixture of isoquinoline-3-carboxylic acid and NiCl₂·6H₂O (molar ratio 4:1) at room temperature. Blue prismatic crystals of (III) were obtained by slow evaporation of a methanol solution of a mixture of isoquinoline-3-carboxylic acid and CuCl₂·2H₂O (molar ratio 4:1) at room temperature.

S3. Refinement

All H atoms were initially located in difference Fourier maps and were then regenerated in their ideal positions, with C—H = 0.96 (methyl) or 0.93 Å (other H atoms), and U_iso(H) = 1.2U_eq(parent) (methyl) or 1.5U_eq(parent) (other H atoms). The weighting schemes for both all three? structures were optimized.

Computing details

For all compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures

Fig. 1. A drawing of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The corresponding drawings for (II) and (III) are similar.

(I)

Crystal data

[Co(C10H6NO2)2(CH4O)2]	F(000) = 482.0
Mr = 467.33	Dx = 1.562 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.732 (2) Å	θ = 13.4–14.5°
b = 6.268 (2) Å	µ = 0.91 mm^−1
c = 15.043 (2) Å	T = 296 K
β = 101.00 (1)°	Plate, orange
V = 993.3 (4) Å^3	0.25 × 0.15 × 0.15 mm
Z = 2

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.019
ω/2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→13
Tmin = 0.848, Tmax = 0.873	k = 0→8
2613 measured reflections	l = −19→19
2275 independent reflections	3 standard reflections every 150 reflections
1618 reflections with I > 2σ(I)	intensity decay: 0.1%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0379P)^2 + 0.2358P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.092	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.33 e Å^−3
1618 reflections	Δρmin = −0.23 e Å^−3
144 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Co	0.0000	0.0000	0.0000	0.0271 (1)
O1	0.0377 (1)	−0.2841 (3)	−0.0571 (1)	0.0338 (4)
O1m	−0.0385 (2)	−0.1656 (3)	0.1169 (1)	0.0354 (4)
O2	0.1927 (2)	−0.5179 (3)	−0.0645 (1)	0.0419 (4)
N1	0.1981 (2)	−0.0164 (3)	0.0465 (1)	0.0274 (4)
C1	0.2467 (2)	−0.2053 (4)	0.0212 (1)	0.0268 (4)
C2	0.3715 (2)	−0.2560 (4)	0.0448 (1)	0.0291 (5)
C3	0.4582 (2)	−0.1105 (4)	0.0949 (1)	0.0281 (5)
C4	0.5910 (2)	−0.1483 (4)	0.1189 (2)	0.0355 (5)
C5	0.6683 (2)	0.0038 (5)	0.1639 (2)	0.0407 (6)
C6	0.6192 (2)	0.1996 (5)	0.1878 (2)	0.0421 (6)
C7	0.4922 (2)	0.2397 (4)	0.1668 (2)	0.0349 (5)
C8	0.4088 (2)	0.0857 (4)	0.1195 (1)	0.0278 (4)
C9	0.2767 (2)	0.1209 (4)	0.0937 (1)	0.0287 (5)
C10	0.1509 (2)	−0.3485 (4)	−0.0379 (2)	0.0292 (5)
C11	0.0531 (3)	−0.2310 (6)	0.1926 (2)	0.0574 (8)
H1m	−0.0846	−0.2654	0.0982	0.0424*
H2	0.4002	−0.3872	0.0280	0.0349*
H4	0.6248	−0.2770	0.1038	0.0426*
H5	0.7551	−0.0217	0.1793	0.0488*
H6	0.6739	0.3023	0.2182	0.0505*
H7	0.4605	0.3685	0.1835	0.0419*
H9	0.2436	0.2481	0.1111	0.0344*
H11a	0.1023	−0.3464	0.1753	0.0861*
H11b	0.0110	−0.2776	0.2401	0.0861*
H11c	0.1081	−0.1134	0.2138	0.0861*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0191 (2)	0.0245 (2)	0.0361 (2)	0.0026 (2)	0.0007 (2)	−0.0034 (2)
O1	0.0253 (8)	0.0298 (9)	0.0443 (9)	0.0025 (7)	0.0012 (7)	−0.0077 (7)
O1m	0.0315 (8)	0.0314 (9)	0.0409 (9)	−0.0038 (7)	0.0008 (7)	0.0002 (7)
O2	0.0319 (9)	0.0301 (9)	0.064 (1)	0.0013 (7)	0.0101 (8)	−0.0162 (9)
N1	0.0211 (8)	0.0260 (9)	0.0342 (9)	0.0036 (8)	0.0033 (7)	−0.0006 (8)
C1	0.025 (1)	0.024 (1)	0.032 (1)	0.0017 (9)	0.0067 (8)	0.0000 (9)
C2	0.028 (1)	0.025 (1)	0.035 (1)	0.0062 (9)	0.0073 (9)	−0.0006 (10)
C3	0.023 (1)	0.032 (1)	0.029 (1)	0.0027 (10)	0.0041 (9)	0.0030 (9)
C4	0.025 (1)	0.044 (1)	0.038 (1)	0.007 (1)	0.0076 (9)	0.001 (1)
C5	0.020 (1)	0.061 (2)	0.040 (1)	0.001 (1)	0.0026 (9)	−0.001 (1)
C6	0.028 (1)	0.055 (2)	0.041 (1)	−0.009 (1)	0.002 (1)	−0.008 (1)
C7	0.030 (1)	0.039 (1)	0.035 (1)	−0.001 (1)	0.0043 (10)	−0.006 (1)
C8	0.023 (1)	0.034 (1)	0.027 (1)	0.0004 (9)	0.0052 (8)	0.0006 (9)
C9	0.026 (1)	0.027 (1)	0.034 (1)	0.0029 (9)	0.0061 (9)	−0.0035 (9)
C10	0.027 (1)	0.026 (1)	0.035 (1)	−0.0005 (9)	0.0078 (9)	−0.0013 (9)
C11	0.047 (2)	0.074 (2)	0.045 (2)	−0.004 (2)	−0.006 (1)	0.014 (2)

Geometric parameters (Å, º)

Co—O1	2.050 (2)	C3—C4	1.421 (3)
Co—O1^i	2.050 (2)	C3—C8	1.416 (3)
Co—O1m	2.148 (2)	C4—C5	1.357 (3)
Co—O1m^i	2.148 (2)	C4—H4	0.930
Co—N1	2.110 (2)	C5—C6	1.409 (4)
Co—N1^i	2.110 (2)	C5—H5	0.930
O1—C10	1.260 (3)	C6—C7	1.362 (3)
O1m—C11	1.416 (3)	C6—H6	0.930
O1m—H1m	0.814	C7—C8	1.413 (3)
O2—C10	1.248 (3)	C7—H7	0.930
N1—C1	1.376 (3)	C8—C9	1.414 (3)
N1—C9	1.314 (3)	C9—H9	0.930
C1—C2	1.357 (3)	C11—H11a	0.960
C1—C10	1.518 (3)	C11—H11b	0.960
C2—C3	1.414 (3)	C11—H11c	0.960
C2—H2	0.930
O1···O1^ii	3.385 (3)	O2···C11^ii	3.348 (3)
O1···C10^ii	3.542 (3)	O2···N1^iv	3.538 (3)
O1···O1m^ii	3.565 (2)	O2···C6^vi	3.596 (3)
O1···O2^ii	3.566 (3)	C1···C5^vi	3.340 (3)
O1m···O2^ii	2.607 (2)	C2···C5^vi	3.469 (3)
O1m···C10^ii	3.405 (3)	C2···C6^vi	3.537 (3)
O1m···C5^iii	3.518 (3)	C3···C3^vi	3.441 (4)
O2···C9^iv	3.283 (3)	C3···C4^vi	3.550 (3)
O2···C4^v	3.341 (3)	C4···C7^vii	3.576 (4)
O1—Co—O1^i	180.0	C2—C3—C8	117.3 (2)
O1—Co—O1m	90.42 (6)	C4—C3—C8	119.1 (2)
O1—Co—O1m^i	89.58 (6)	C3—C4—C5	119.8 (2)
O1—Co—N1	80.21 (6)	C3—C4—H4	120.1
O1—Co—N1^i	99.79 (6)	C5—C4—H4	120.1
O1^i—Co—O1m	89.58 (6)	C4—C5—C6	121.1 (2)
O1^i—Co—O1m^i	90.42 (6)	C4—C5—H5	119.4
O1^i—Co—N1	99.79 (6)	C6—C5—H5	119.4
O1^i—Co—N1^i	80.21 (6)	C5—C6—C7	120.5 (2)
O1m—Co—O1m^i	180.0	C5—C6—H6	119.8
O1m—Co—N1	92.51 (7)	C7—C6—H6	119.8
O1m—Co—N1^i	87.49 (7)	C6—C7—C8	120.1 (2)
O1m^i—Co—N1	87.49 (7)	C6—C7—H7	120.0
O1m^i—Co—N1^i	92.51 (7)	C8—C7—H7	120.0
N1—Co—N1^i	180.0	C3—C8—C7	119.4 (2)
Co—O1—C10	116.2 (1)	C3—C8—C9	118.0 (2)
Co—O1m—C11	125.9 (2)	C7—C8—C9	122.5 (2)
Co—O1m—H1m	106.7	N1—C9—C8	123.5 (2)
C11—O1m—H1m	109.8	N1—C9—H9	118.2
Co—N1—C1	111.2 (1)	C8—C9—H9	118.2
Co—N1—C9	130.5 (2)	O1—C10—O2	126.1 (2)
C1—N1—C9	118.4 (2)	O1—C10—C1	117.4 (2)
N1—C1—C2	122.4 (2)	O2—C10—C1	116.5 (2)
N1—C1—C10	114.9 (2)	O1m—C11—H11a	109.5
C2—C1—C10	122.6 (2)	O1m—C11—H11b	109.5
C1—C2—C3	120.3 (2)	O1m—C11—H11c	109.5
C1—C2—H2	119.8	H11a—C11—H11b	109.5
C3—C2—H2	119.8	H11a—C11—H11c	109.5
C2—C3—C4	123.6 (2)	H11b—C11—H11c	109.5
Co—O1—C10—O2	178.9 (2)	N1—Co—O1—C10	3.6 (2)
Co—O1—C10—C1	−2.6 (3)	N1—Co—O1^i—C10^i	176.4 (2)
Co—O1^i—C10^i—O2^i	−178.9 (2)	N1—Co—O1m—C11	4.1 (2)
Co—O1^i—C10^i—C1^i	2.6 (3)	N1—Co—O1m^i—C11^i	175.9 (2)
Co—N1—C1—C2	−178.5 (2)	N1—C1—C2—C3	−2.0 (3)
Co—N1—C1—C10	3.7 (2)	N1—C9—C8—C3	−1.6 (3)
Co—N1—C9—C8	−179.7 (2)	N1—C9—C8—C7	177.1 (2)
Co—N1^i—C1^i—C2^i	178.5 (2)	C1—N1—C9—C8	0.4 (3)
Co—N1^i—C1^i—C10^i	−3.7 (2)	C1—C2—C3—C4	−177.3 (2)
Co—N1^i—C9^i—C8^i	179.7 (2)	C1—C2—C3—C8	0.7 (3)
O1—Co—O1m—C11	84.3 (2)	C2—C1—N1—C9	1.5 (3)
O1—Co—O1m^i—C11^i	95.7 (2)	C2—C3—C4—C5	177.3 (2)
O1—Co—N1—C1	−3.9 (1)	C2—C3—C8—C7	−177.8 (2)
O1—Co—N1—C9	176.2 (2)	C2—C3—C8—C9	1.0 (3)
O1—Co—N1^i—C1^i	−176.1 (1)	C3—C2—C1—C10	175.7 (2)
O1—Co—N1^i—C9^i	3.8 (2)	C3—C4—C5—C6	0.2 (4)
O1—C10—C1—N1	−0.9 (3)	C3—C8—C7—C6	0.4 (3)
O1—C10—C1—C2	−178.7 (2)	C4—C3—C8—C7	0.4 (3)
O1m—Co—O1—C10	−88.9 (2)	C4—C3—C8—C9	179.1 (2)
O1m—Co—O1^i—C10^i	−91.1 (2)	C4—C5—C6—C7	0.6 (4)
O1m—Co—N1—C1	86.1 (1)	C5—C4—C3—C8	−0.7 (4)
O1m—Co—N1—C9	−93.8 (2)	C5—C6—C7—C8	−0.9 (4)
O1m—Co—N1^i—C1^i	93.9 (1)	C6—C7—C8—C9	−178.2 (2)
O1m—Co—N1^i—C9^i	−86.2 (2)	C9—N1—C1—C10	−176.4 (2)
O2—C10—C1—N1	177.8 (2)	C9—N1—C1—C10	−176.4 (2)
O2—C10—C1—C2	−0.1 (3)

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y−1, −z; (iii) x−1, y, z; (iv) x, y−1, z; (v) −x+1, −y−1, −z; (vi) −x+1, −y, −z; (vii) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1m—H1m···O2^ii	0.81	1.80	2.607 (2)	175

Symmetry code: (ii) −x, −y−1, −z.

(II)

Crystal data

[Ni(C10H6NO2)2(CH4O)2]	F(000) = 484
Mr = 467.09	Dx = 1.571 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.638 (2) Å	θ = 13.5–14.9°
b = 6.277 (2) Å	µ = 1.03 mm^−1
c = 15.068 (2) Å	T = 296 K
β = 101.15 (1)°	Plate, colourless
V = 987.2 (4) Å^3	0.30 × 0.20 × 0.15 mm
Z = 2

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.019
ω/2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→13
Tmin = 0.821, Tmax = 0.857	k = 0→8
2602 measured reflections	l = −19→19
2267 independent reflections	3 standard reflections every 150 reflections
1590 reflections with I > 2σ(I)	intensity decay: 0.03%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0376P)^2 + 0.449P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.096	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.33 e Å^−3
1590 reflections	Δρmin = −0.40 e Å^−3
144 parameters

Special details

Refinement. Refinement using reflections with F² > −10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni	0.0000	0.0000	0.0000	0.0263 (1)
O1	0.0312 (2)	−0.2834 (3)	−0.0578 (1)	0.0326 (4)
O1m	−0.0379 (2)	−0.1588 (3)	0.1159 (1)	0.0349 (4)
O2	0.1871 (2)	−0.5167 (3)	−0.0668 (1)	0.0405 (5)
N1	0.1942 (2)	−0.0180 (3)	0.0446 (1)	0.0267 (4)
C1	0.2424 (2)	−0.2062 (4)	0.0197 (2)	0.0265 (5)
C2	0.3684 (2)	−0.2567 (4)	0.0437 (2)	0.0288 (5)
C3	0.4559 (2)	−0.1119 (4)	0.0940 (2)	0.0279 (5)
C4	0.5895 (2)	−0.1499 (5)	0.1186 (2)	0.0354 (6)
C5	0.6679 (2)	0.0030 (5)	0.1634 (2)	0.0411 (6)
C6	0.6182 (3)	0.1971 (5)	0.1873 (2)	0.0424 (7)
C7	0.4899 (2)	0.2385 (5)	0.1658 (2)	0.0339 (6)
C8	0.4061 (2)	0.0842 (4)	0.1183 (2)	0.0271 (5)
C9	0.2726 (2)	0.1204 (4)	0.0918 (2)	0.0287 (5)
C10	0.1454 (2)	−0.3487 (4)	−0.0398 (2)	0.0295 (5)
C11	0.0527 (3)	−0.2086 (6)	0.1945 (2)	0.0586 (10)
H1m	−0.0890	−0.2740	0.1000	0.0419*
H2	0.3974	−0.3877	0.0269	0.0346*
H4	0.6235	−0.2790	0.1042	0.0425*
H5	0.7557	−0.0217	0.1785	0.0494*
H6	0.6734	0.2991	0.2181	0.0509*
H7	0.4579	0.3673	0.1823	0.0407*
H9	0.2390	0.2476	0.1087	0.0344*
H11a	0.1045	−0.3261	0.1822	0.0879*
H11b	0.0089	−0.2467	0.2423	0.0879*
H11c	0.1063	−0.0870	0.2125	0.0879*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0175 (2)	0.0232 (2)	0.0364 (3)	0.0024 (2)	0.0006 (2)	−0.0032 (2)
O1	0.0233 (9)	0.0263 (9)	0.046 (1)	0.0006 (7)	0.0004 (8)	−0.0076 (8)
O1m	0.0309 (10)	0.0325 (10)	0.039 (1)	−0.0044 (8)	0.0004 (8)	0.0007 (9)
O2	0.0306 (9)	0.0279 (10)	0.063 (1)	−0.0004 (8)	0.0095 (9)	−0.014 (1)
N1	0.0196 (9)	0.026 (1)	0.034 (1)	0.0050 (9)	0.0022 (7)	−0.0007 (10)
C1	0.024 (1)	0.023 (1)	0.033 (1)	0.0008 (10)	0.0068 (10)	0.001 (1)
C2	0.024 (1)	0.026 (1)	0.038 (1)	0.005 (1)	0.0075 (10)	−0.001 (1)
C3	0.023 (1)	0.032 (1)	0.029 (1)	0.004 (1)	0.0039 (10)	0.001 (1)
C4	0.024 (1)	0.044 (2)	0.039 (1)	0.008 (1)	0.008 (1)	0.001 (1)
C5	0.018 (1)	0.063 (2)	0.040 (1)	0.002 (1)	0.0018 (10)	0.001 (2)
C6	0.028 (1)	0.054 (2)	0.043 (2)	−0.008 (1)	0.002 (1)	−0.008 (1)
C7	0.028 (1)	0.036 (1)	0.037 (1)	−0.001 (1)	0.004 (1)	−0.005 (1)
C8	0.023 (1)	0.031 (1)	0.028 (1)	−0.001 (1)	0.0047 (10)	0.001 (1)
C9	0.024 (1)	0.027 (1)	0.035 (1)	0.002 (1)	0.004 (1)	−0.004 (1)
C10	0.026 (1)	0.026 (1)	0.037 (1)	−0.002 (1)	0.007 (1)	−0.002 (1)
C11	0.045 (2)	0.077 (3)	0.047 (2)	−0.006 (2)	−0.007 (1)	0.013 (2)

Geometric parameters (Å, º)

Ni—O1	2.036 (2)	C3—C4	1.418 (3)
Ni—O1^i	2.036 (2)	C3—C8	1.416 (4)
Ni—O1m	2.116 (2)	C4—C5	1.362 (4)
Ni—O1m^i	2.116 (2)	C4—H4	0.930
Ni—N1	2.049 (2)	C5—C6	1.403 (5)
Ni—N1^i	2.049 (2)	C5—H5	0.930
O1—C10	1.261 (3)	C6—C7	1.365 (4)
O1m—C11	1.410 (3)	C6—H6	0.930
O1m—H1m	0.908	C7—C8	1.413 (4)
O2—C10	1.243 (3)	C7—H7	0.930
N1—C1	1.368 (3)	C8—C9	1.417 (3)
N1—C9	1.314 (3)	C9—H9	0.930
C1—C2	1.357 (3)	C11—H11a	0.960
C1—C10	1.521 (3)	C11—H11b	0.960
C2—C3	1.412 (3)	C11—H11c	0.960
C2—H2	0.930
O1···O1^ii	3.364 (4)	C3···C3^vi	3.450 (5)
O1···C10^ii	3.478 (3)	C3···C4^vi	3.549 (4)
O1···O2^ii	3.491 (3)	C4···C7^vii	3.580 (4)
O1m···O2^ii	2.600 (3)	O1···O1m^i	2.915 (3)
O1m···C10^ii	3.416 (3)	O1···O1m	2.957 (3)
O1m···C5^iii	3.494 (3)	O1···O1^ii	3.364 (4)
O2···C9^iv	3.300 (3)	O1···O2^ii	3.491 (3)
O2···C11^ii	3.359 (4)	O1m···O2^ii	2.600 (3)
O2···C4^v	3.369 (4)	O1m···O1^i	2.915 (3)
O2···N1^iv	3.560 (3)	O1m···O1	2.957 (3)
C1···C5^vi	3.343 (4)	O2···O1m^ii	2.600 (3)
C2···C5^vi	3.459 (4)	O2···O1^ii	3.491 (3)
C2···C6^vi	3.531 (4)
O1—Ni—O1^i	180.0	C6—C7—C8	119.6 (3)
O1—Ni—O1m	90.81 (7)	C6—C7—H7	120.2
O1—Ni—O1m^i	89.19 (7)	C8—C7—H7	120.2
O1—Ni—N1	81.63 (7)	C3—C8—C7	119.7 (2)
O1—Ni—N1^i	98.37 (7)	C3—C8—C9	118.1 (2)
O1^i—Ni—O1m	89.19 (7)	C7—C8—C9	122.2 (2)
O1^i—Ni—O1m^i	90.81 (7)	N1—C9—C8	122.9 (2)
O1^i—Ni—N1	98.37 (7)	N1—C9—H9	118.6
O1^i—Ni—N1^i	81.63 (7)	C8—C9—H9	118.6
O1m—Ni—O1m^i	180.0	O1—C10—O2	126.6 (2)
O1m—Ni—N1	92.55 (7)	O1—C10—C1	116.8 (2)
O1m—Ni—N1^i	87.45 (7)	O2—C10—C1	116.6 (2)
O1m^i—Ni—N1	87.45 (7)	O1m—C11—H11a	109.5
O1m^i—Ni—N1^i	92.55 (7)	O1m—C11—H11b	109.5
N1—Ni—N1^i	180.0	O1m—C11—H11c	109.5
Ni—O1—C10	115.0 (2)	H11a—C11—H11b	109.5
Ni—O1m—C11	126.1 (2)	H11a—C11—H11c	109.5
Ni—O1m—H1m	111.0	H11b—C11—H11c	109.5
C11—O1m—H1m	108.8	O2—O1—O1m^i	122.95 (10)
Ni—N1—C1	111.4 (1)	O2—O1—O1m	122.79 (9)
Ni—N1—C9	129.4 (2)	O2—O1—O1^ii	74.06 (8)
C1—N1—C9	119.2 (2)	O2—O1—O2^ii	112.08 (8)
N1—C1—C2	122.1 (2)	O2—O1—O1m^ii	45.66 (6)
N1—C1—C10	115.0 (2)	O1m^i—O1—O1m	92.21 (7)
C2—C1—C10	122.8 (2)	O1m^i—O1—O1^ii	160.7 (1)
C1—C2—C3	120.4 (2)	O1m^i—O1—O2^ii	124.13 (7)
C1—C2—H2	119.8	O1m^i—O1—O1m^ii	147.90 (9)
C3—C2—H2	119.8	O1m—O1—O1^ii	69.38 (7)
C2—C3—C4	123.7 (2)	O1m—O1—O2^ii	46.66 (5)
C2—C3—C8	117.3 (2)	O1m—O1—O1m^ii	119.38 (7)
C4—C3—C8	119.0 (2)	O1^ii—O1—O1m^ii	49.99 (6)
C3—C4—C5	119.9 (3)	O2^ii—O1—O1m^ii	80.11 (6)
C3—C4—H4	120.1	O2^ii—O1m—O1^i	135.19 (8)
C5—C4—H4	120.1	O2^ii—O1m—O1	77.53 (8)
C4—C5—C6	120.9 (2)	O1^i—O1m—O1	87.79 (7)
C4—C5—H5	119.5	O1^i—O1m—O1^ii	147.90 (9)
C6—C5—H5	119.5	O1—O1m—O1^ii	60.62 (7)
C5—C6—C7	120.9 (3)	O1—O2—O1m^ii	96.38 (9)
C5—C6—H6	119.5	O1—O2—O1^ii	67.92 (8)
C7—C6—H6	119.6	O1m^ii—O2—O1^ii	55.80 (6)
Ni—O1—C10—O2	179.7 (2)	N1—Ni—O1—C10	2.9 (2)
Ni—O1—C10—C1	−1.3 (3)	N1—Ni—O1^i—C10^i	177.1 (2)
Ni—O1^i—C10^i—O2^i	−179.7 (2)	N1—Ni—O1m—C11	9.5 (2)
Ni—O1^i—C10^i—C1^i	1.3 (3)	N1—Ni—O1m^i—C11^i	170.5 (2)
Ni—N1—C1—C2	−178.2 (2)	N1—C1—C2—C3	−1.7 (4)
Ni—N1—C1—C10	4.3 (3)	N1—C9—C8—C3	−1.3 (4)
Ni—N1—C9—C8	179.6 (2)	N1—C9—C8—C7	177.2 (2)
Ni—N1^i—C1^i—C2^i	178.2 (2)	C1—N1—C9—C8	0.3 (4)
Ni—N1^i—C1^i—C10^i	−4.3 (3)	C1—C2—C3—C4	−177.6 (3)
Ni—N1^i—C9^i—C8^i	−179.6 (2)	C1—C2—C3—C8	0.6 (4)
O1—Ni—O1m—C11	91.1 (2)	C2—C1—N1—C9	1.2 (4)
O1—Ni—O1m^i—C11^i	88.9 (2)	C2—C3—C4—C5	176.8 (3)
O1—Ni—N1—C1	−3.9 (2)	C2—C3—C8—C7	−177.7 (2)
O1—Ni—N1—C9	176.7 (2)	C2—C3—C8—C9	0.9 (4)
O1—Ni—N1^i—C1^i	−176.1 (2)	C3—C2—C1—C10	175.6 (2)
O1—Ni—N1^i—C9^i	3.3 (2)	C3—C4—C5—C6	1.2 (4)
O1—C10—C1—N1	−2.1 (3)	C3—C8—C7—C6	0.4 (4)
O1—C10—C1—C2	−179.6 (2)	C4—C3—C8—C7	0.5 (4)
O1m—Ni—O1—C10	−89.6 (2)	C4—C3—C8—C9	179.1 (2)
O1m—Ni—O1^i—C10^i	−90.4 (2)	C4—C5—C6—C7	−0.3 (5)
O1m—Ni—N1—C1	86.5 (2)	C5—C4—C3—C8	−1.3 (4)
O1m—Ni—N1—C9	−92.8 (2)	C5—C6—C7—C8	−0.5 (4)
O1m—Ni—N1^i—C1^i	93.5 (2)	C6—C7—C8—C9	−178.1 (3)
O1m—Ni—N1^i—C9^i	−87.2 (2)	C9—N1—C1—C10	−176.2 (2)
O2—C10—C1—N1	177.0 (2)	C9—N1—C1—C10	−176.2 (2)
O2—C10—C1—C2	−0.5 (4)

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y−1, −z; (iii) x−1, y, z; (iv) x, y−1, z; (v) −x+1, −y−1, −z; (vi) −x+1, −y, −z; (vii) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1m—H1m···O2^ii	0.91	1.69	2.600 (3)	178

Symmetry code: (ii) −x, −y−1, −z.

(III)

Crystal data

[Cu(C10H6NO2)2(CH4O)2]	F(000) = 486.0
Mr = 471.95	Dx = 1.541 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.265 (2) Å	θ = 14.7–15.0°
b = 6.332 (2) Å	µ = 1.12 mm^−1
c = 15.764 (1) Å	T = 296 K
β = 96.879 (9)°	Plate, blue
V = 1017.3 (4) Å^3	0.30 × 0.30 × 0.20 mm
Z = 2

Data collection

Rigaku AFC-5R diffractometer	Rint = 0.012
ω/2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→13
Tmin = 0.720, Tmax = 0.800	k = 0→8
2692 measured reflections	l = −20→20
2339 independent reflections	3 standard reflections every 150 reflections
1665 reflections with I > 2σ(I)	intensity decay: 14.8%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 0.4271P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.26 e Å^−3
2239 reflections	Δρmin = −0.27 e Å^−3
143 parameters

Special details

Refinement. Refinement using reflections with F² > −10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu	0.0000	0.0000	0.0000	0.0403 (1)
O1	0.0358 (2)	−0.2700 (3)	−0.0538 (1)	0.0436 (4)
O1m	−0.0418 (2)	−0.1899 (3)	0.1343 (1)	0.0551 (5)
O2	0.1970 (2)	−0.5029 (3)	−0.0623 (1)	0.0535 (5)
N1	0.1896 (2)	−0.0088 (3)	0.0416 (1)	0.0352 (4)
C1	0.2447 (2)	−0.1953 (3)	0.0196 (2)	0.0351 (5)
C2	0.3729 (2)	−0.2423 (4)	0.0449 (2)	0.0380 (5)
C3	0.4540 (2)	−0.0958 (4)	0.0937 (1)	0.0357 (5)
C4	0.5893 (2)	−0.1302 (4)	0.1196 (2)	0.0435 (6)
C5	0.6627 (2)	0.0223 (5)	0.1634 (2)	0.0496 (6)
C6	0.6059 (3)	0.2147 (5)	0.1848 (2)	0.0511 (7)
C7	0.4753 (2)	0.2517 (4)	0.1615 (2)	0.0441 (6)
C8	0.3969 (2)	0.0980 (4)	0.1151 (1)	0.0364 (5)
C9	0.2623 (2)	0.1308 (4)	0.0874 (1)	0.0377 (5)
C10	0.1528 (2)	−0.3365 (4)	−0.0362 (2)	0.0389 (5)
C11	0.0543 (3)	−0.2684 (6)	0.1968 (2)	0.0755 (10)
H1m	−0.0894	−0.2869	0.1151	0.0826*
H2	0.4071	−0.3713	0.0300	0.0456*
H4	0.6280	−0.2571	0.1066	0.0522*
H5	0.7517	−0.0008	0.1795	0.0595*
H6	0.6575	0.3170	0.2148	0.0613*
H7	0.4382	0.3784	0.1763	0.0529*
H9	0.2236	0.2562	0.1021	0.0453*
H11a	0.1169	−0.1592	0.2139	0.1133*
H11b	0.0981	−0.3856	0.1741	0.1133*
H11c	0.0137	−0.3140	0.2455	0.1133*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0277 (2)	0.0325 (2)	0.0597 (3)	0.0067 (2)	0.0009 (2)	−0.0079 (2)
O1	0.0341 (8)	0.0351 (9)	0.061 (1)	0.0052 (7)	0.0010 (8)	−0.0079 (8)
O1m	0.051 (1)	0.045 (1)	0.067 (1)	−0.0024 (9)	−0.0048 (9)	0.0005 (9)
O2	0.0394 (9)	0.0364 (9)	0.085 (1)	0.0051 (8)	0.0094 (9)	−0.0189 (10)
N1	0.0294 (8)	0.0305 (9)	0.0459 (10)	0.0069 (8)	0.0056 (7)	−0.0025 (9)
C1	0.032 (1)	0.029 (1)	0.045 (1)	0.0043 (9)	0.0091 (9)	0.0017 (9)
C2	0.034 (1)	0.034 (1)	0.047 (1)	0.0083 (10)	0.0095 (10)	0.001 (1)
C3	0.030 (1)	0.041 (1)	0.037 (1)	0.005 (1)	0.0066 (9)	0.005 (1)
C4	0.032 (1)	0.052 (1)	0.046 (1)	0.011 (1)	0.005 (1)	0.004 (1)
C5	0.031 (1)	0.070 (2)	0.047 (1)	0.003 (1)	0.0009 (10)	0.002 (1)
C6	0.040 (1)	0.065 (2)	0.046 (1)	−0.006 (1)	−0.002 (1)	−0.006 (1)
C7	0.041 (1)	0.047 (1)	0.045 (1)	0.002 (1)	0.006 (1)	−0.008 (1)
C8	0.033 (1)	0.039 (1)	0.037 (1)	0.004 (1)	0.0063 (9)	−0.001 (1)
C9	0.035 (1)	0.033 (1)	0.045 (1)	0.0080 (10)	0.0059 (10)	−0.003 (1)
C10	0.035 (1)	0.032 (1)	0.051 (1)	0.0024 (10)	0.010 (1)	−0.002 (1)
C11	0.068 (2)	0.084 (2)	0.070 (2)	0.002 (2)	−0.011 (2)	0.017 (2)

Geometric parameters (Å, º)

Cu—O1	1.963 (2)	C3—C4	1.417 (3)
Cu—O1^i	1.963 (2)	C3—C8	1.418 (3)
Cu—O1m	2.516 (2)	C4—C5	1.361 (4)
Cu—O1m^i	2.516 (2)	C4—H4	0.930
Cu—N1	1.979 (2)	C5—C6	1.408 (4)
Cu—N1^i	1.979 (2)	C5—H5	0.930
O1—C10	1.272 (3)	C6—C7	1.367 (3)
O1m—C11	1.399 (4)	C6—H6	0.930
O1m—H1m	0.820	C7—C8	1.410 (3)
O2—C10	1.236 (3)	C7—H7	0.930
N1—C1	1.372 (3)	C8—C9	1.414 (3)
N1—C9	1.315 (3)	C9—H9	0.930
C1—C2	1.361 (3)	C11—H11a	0.960
C1—C10	1.504 (3)	C11—H11b	0.960
C2—C3	1.412 (3)	C11—H11c	0.960
C2—H2	0.930
Cu···O1m	2.516 (2)	O2···C4^v	3.391 (3)
Cu···O1m^i	2.516 (2)	O2···C11^ii	3.455 (4)
O1···O2^ii	3.489 (3)	O2···C6^vi	3.476 (3)
O1···O1^ii	3.494 (3)	C1···C5^vi	3.328 (4)
O1···C10^ii	3.554 (3)	C1···C4^vi	3.586 (4)
O1m···O2^ii	2.679 (2)	C2···C5^vi	3.545 (4)
O1m···C5^iii	3.399 (3)	C2···C4^vi	3.560 (4)
O1m···C10^ii	3.502 (3)	C3···C3^vi	3.428 (5)
O2···C9^iv	3.319 (3)	C5···C10^vi	3.531 (4)
O1—Cu—O1^i	180.0	C2—C3—C8	117.7 (2)
O1—Cu—O1m	90.41 (7)	C4—C3—C8	118.9 (2)
O1—Cu—O1m^i	89.59 (7)	C3—C4—C5	120.1 (2)
O1—Cu—N1	83.77 (7)	C3—C4—H4	120.0
O1—Cu—N1^i	96.23 (7)	C5—C4—H4	120.0
O1^i—Cu—O1m	89.59 (7)	C4—C5—C6	121.0 (2)
O1^i—Cu—O1m^i	90.41 (7)	C4—C5—H5	119.5
O1^i—Cu—N1	96.23 (7)	C6—C5—H5	119.5
O1^i—Cu—N1^i	83.77 (7)	C5—C6—C7	120.3 (2)
O1m—Cu—O1m^i	180.0	C5—C6—H6	119.8
O1m—Cu—N1	88.14 (7)	C7—C6—H6	119.8
O1m—Cu—N1^i	91.86 (7)	C6—C7—C8	120.1 (2)
O1m^i—Cu—N1	91.86 (7)	C6—C7—H7	120.0
O1m^i—Cu—N1^i	88.14 (7)	C8—C7—H7	120.0
N1—Cu—N1^i	180.0	C3—C8—C7	119.6 (2)
Cu—O1—C10	114.5 (1)	C3—C8—C9	118.0 (2)
Cu—O1m—C11	125.9 (2)	C7—C8—C9	122.3 (2)
Cu—O1m—H1m	101.6	N1—C9—C8	122.7 (2)
C11—O1m—H1m	109.4	N1—C9—H9	118.6
Cu—N1—C1	111.0 (1)	C8—C9—H9	118.7
Cu—N1—C9	129.3 (2)	O1—C10—O2	125.7 (2)
C1—N1—C9	119.6 (2)	O1—C10—C1	116.1 (2)
N1—C1—C2	121.8 (2)	O2—C10—C1	118.1 (2)
N1—C1—C10	114.3 (2)	O1m—C11—H11a	109.5
C2—C1—C10	123.9 (2)	O1m—C11—H11b	109.5
C1—C2—C3	120.2 (2)	O1m—C11—H11c	109.5
C1—C2—H2	119.9	H11a—C11—H11b	109.5
C3—C2—H2	119.9	H11a—C11—H11c	109.5
C2—C3—C4	123.4 (2)	H11b—C11—H11c	109.5
Cu—O1—C10—O2	179.4 (2)	N1—Cu—O1—C10	4.0 (2)
Cu—O1—C10—C1	−2.2 (3)	N1—Cu—O1^i—C10^i	176.0 (2)
Cu—O1^i—C10^i—O2^i	−179.4 (2)	N1—Cu—O1m—C11	−5.2 (2)
Cu—O1^i—C10^i—C1^i	2.2 (3)	N1—Cu—O1m^i—C11^i	−174.8 (2)
Cu—N1—C1—C2	−176.7 (2)	N1—C1—C2—C3	−1.3 (4)
Cu—N1—C1—C10	5.1 (2)	N1—C9—C8—C3	−1.2 (3)
Cu—N1—C9—C8	177.5 (2)	N1—C9—C8—C7	177.6 (2)
Cu—N1^i—C1^i—C2^i	176.7 (2)	C1—N1—C9—C8	0.3 (3)
Cu—N1^i—C1^i—C10^i	−5.1 (2)	C1—C2—C3—C4	−177.5 (2)
Cu—N1^i—C9^i—C8^i	−177.5 (2)	C1—C2—C3—C8	0.4 (3)
O1—Cu—O1m—C11	78.5 (2)	C2—C1—N1—C9	1.0 (3)
O1—Cu—O1m^i—C11^i	101.5 (2)	C2—C3—C4—C5	177.1 (2)
O1—Cu—N1—C1	−4.9 (2)	C2—C3—C8—C7	−178.0 (2)
O1—Cu—N1—C9	177.7 (2)	C2—C3—C8—C9	0.8 (3)
O1—Cu—N1^i—C1^i	−175.1 (2)	C3—C2—C1—C10	176.7 (2)
O1—Cu—N1^i—C9^i	2.3 (2)	C3—C4—C5—C6	0.8 (4)
O1—C10—C1—N1	−2.1 (3)	C3—C8—C7—C6	0.7 (4)
O1—C10—C1—C2	179.7 (2)	C4—C3—C8—C7	0.0 (3)
O1m—Cu—O1—C10	−84.1 (2)	C4—C3—C8—C9	178.9 (2)
O1m—Cu—O1^i—C10^i	−95.9 (2)	C4—C5—C6—C7	−0.1 (4)
O1m—Cu—N1—C1	85.7 (2)	C5—C4—C3—C8	−0.8 (4)
O1m—Cu—N1—C9	−91.7 (2)	C5—C6—C7—C8	−0.7 (4)
O1m—Cu—N1^i—C1^i	94.3 (2)	C6—C7—C8—C9	−178.1 (2)
O1m—Cu—N1^i—C9^i	−88.3 (2)	C9—N1—C1—C10	−177.2 (2)
O2—C10—C1—N1	176.5 (2)	C9—N1—C1—C10	−177.2 (2)
O2—C10—C1—C2	−1.7 (4)

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y−1, −z; (iii) x−1, y, z; (iv) x, y−1, z; (v) −x+1, −y−1, −z; (vi) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1m—H1m···O2^ii	0.82	1.86	2.679 (2)	175

Symmetry code: (ii) −x, −y−1, −z.