(2-Formyl-6-methoxy­phenolato-κ2O1,O2)(perchlorato-κO)(1,10-phenanthroline-κ2N,N′)copper(II)

Dong, F.-Y.; Sun, Y.-M.; Li, Y.-T.; Wu, Z.-Y.

doi:10.1107/S1600536808009975

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m678

doi:10.1107/S1600536808009975

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(2-Formyl-6-methoxyphenolato-κ²O¹,O²)(perchlorato-κO)(1,10-phenanthroline-κ²N,N′)copper(II)

Feng-Ying Dong,^a Yun-Ming Sun,^b Yan-Tuan Li ^a ^* and Zhi-Yong Wu ^a

^aMarine Drug and Food Institute, Ocean University of China, Qingdao 266003, People's Republic of China, and ^bDepartment of Plant Protection, Qingdao Agricultural University, Qingdao 266109, People's Republic of China
^*Correspondence e-mail: yantuanli@ouc.edu.cn

(Received 17 March 2008; accepted 11 April 2008; online 16 April 2008)

In the title molecule, [Cu(C₈H₇O₃)(ClO₄)(C₁₂H₈N₂)], the Cu^II ion is five-coordinated by two N atoms [Cu—N = 1.995 (3) and 2.022 (3) Å] from a 1,10-phenanthroline ligand, two O atoms [Cu—O = 1.908 (2) and 1.927 (2) Å] from an o-vanillin ligand and one O atom [Cu—O = 2.510 (3) Å] from a perchlorate anion in a distorted square-pyramidal geometry. Three O atoms of the perchlorate anion are rotationally disordered between two orientations, with occupancies of 0.525 (13) and 0.475 (13). In the crystal structure, two molecules related by a centre of symmetry are paired in such a way that the phenolate O atom from one molecule completes the distorted octahedral Cu coordination in another molecule [Cu⋯O = 2.704 (2) Å].

Related literature

For general background, see: Janzen et al. (2004 ). For related structures, see: Plieger et al. (2004 ); Lin & Zeng (2006 ); Youngme et al. (2005 ).

Experimental

Crystal data

[Cu(C₈H₇O₃)(ClO₄)(C₁₂H₈N₂)]
M_r = 494.33
Monoclinic, C 2/c
a = 22.332 (2) Å
b = 9.3986 (9) Å
c = 18.339 (2) Å
β = 96.733 (2)°
V = 3822.7 (7) Å³
Z = 8
Mo Kα radiation
μ = 1.33 mm⁻¹
T = 298 (2) K
0.26 × 0.17 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.723, T_max = 0.846
9561 measured reflections
3374 independent reflections
2731 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.109
S = 1.00
3374 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009975/cv2393sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009975/cv2393Isup2.hkl

checkCIF report

Comment top

Studies of complexes containing salicylaldehyde and its derivatives have been reported by Janzen et al. (2004) and other groups. The five-coordinated Cu^II complexes have been extensively investigated and the relationship between their structures and reactivities is of major importance. We report here the synthesis and structure of the title complex, (I).

In complex (I), the Cu^II ion is five-coordinated by N1 and N2 atoms from 1,10-phenanthroline ligand, O1 and O2 atoms from o-vanillin and O4 atom from perchlorate anion in a distorted square-pyramidal geometry. Atom O4 lies in the axial position and the equatorial positions are occupied by the other four donor atoms. The bond distances for Cu1—N1 and Cu1—N2 of 2.022 (3)Å and 1.995 (3)Å, respectively, are nearly as long as those found for the similar auxiliary phen ligand (Youngme et al., 2005). The bond lengths for Cu1—O1 and Cu1—O2 of 1.927 (2)Å and 1.908 (2) Å, respectively, are slightly shorter than those of reported o-vanillin complex [1.965 (2) and 1.9201 (17) Å; Lin & Zeng, 2006]. The Cu1—O4 bond distance of 2.510 (3)Å is in the range observed in analogous compound [2.381 (4)Å and 2.559 (4) Å; Plieger et al., 2004]. The larger angles around Cu are near 180°, so the ligands form a satisfactory N₂ O₂ square, with atom O4 inhabiting the axial position. In this way, a distorted square-pyramid is formed (Fig. 1). Three O atoms of perchlorate anion are rotationally disordered between two orientations with the occupancies of 0.525 (13) and 0.475 (13), respectively.

In the crystal, two molecules related by centre of symmetry are paired in such a way, that phenolate O atom from one molecule complete the distorted octahedral Cu coordination [Cu—O 2.704 (2) Å] in another molecule (Fig. 2).

Related literature top

For general background, see: Janzen et al. (2004). For related structures, see: Plieger et al. (2004); Lin & Zeng (2006); Youngme et al. (2005).

Experimental top

To a solution of Cu(ClO₄)₂^.6H₂O (2 mmol, 741 mg) in water (25 ml) was added the mixture of 1,10-phenanthroline (2 mmol, 396 mg), o-vanillin (2 mmol, 304 mg) and NaOH (2 mmol, 40 mg) in ethanol (30 ml) and water (10 ml). The resulting solution was refluxed for 3 h and then concentrated to 40 ml. On standing for a week at room temperature complex (I) formed as green crystals. The crystals were isolated, washed three times with methanol and dried in a vacuum desiccator using anhydrous CaCl₂ (yield 86%). Analysis; calculated for C₂₀H₁₅ClN₂O₇Cu: C, 48.59; H, 3.06; N, 5.67%; Found: C, 48.61; H, 3.08; N, 5.64%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-numbering scheme and 30% probability displacement ellipsoids. Only major part of the disordered perchlorate anion is drawn. H atoms omitted for clarity.
	Fig. 2. A portion of the crystal packing showing the paired molecules with the short intermolecular Cu···O distances (dashed lines) of 2.704 (2) Å. For disordered perchlorate anions, only major parts are drawn. H atoms omitted for clarity.

(2-Formyl-6-methoxyphenolato-κ²O¹,O²)(perchlorato-κO)(1,10- phenanthroline-κ²N,N')copper(II) top

Crystal data top

[Cu(C₈H₇O₃)(ClO₄)(C₁₂H₈N₂)]	F(000) = 2008
M_r = 494.33	D_x = 1.718 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3881 reflections
a = 22.332 (2) Å	θ = 2.2–27.3°
b = 9.3986 (9) Å	µ = 1.33 mm⁻¹
c = 18.339 (2) Å	T = 298 K
β = 96.733 (2)°	Block, green
V = 3822.7 (7) Å³	0.26 × 0.17 × 0.13 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3374 independent reflections
Radiation source: fine-focus sealed tube	2731 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→22
T_min = 0.723, T_max = 0.846	k = −9→11
9561 measured reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0555P)² + 9.3448P] where P = (F_o² + 2F_c²)/3
3374 reflections	(Δ/σ)_max = 0.001
309 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Cu(C₈H₇O₃)(ClO₄)(C₁₂H₈N₂)]	V = 3822.7 (7) Å³
M_r = 494.33	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.332 (2) Å	µ = 1.33 mm⁻¹
b = 9.3986 (9) Å	T = 298 K
c = 18.339 (2) Å	0.26 × 0.17 × 0.13 mm
β = 96.733 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3374 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2731 reflections with I > 2σ(I)
T_min = 0.723, T_max = 0.846	R_int = 0.026
9561 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.01	Δρ_max = 0.52 e Å⁻³
3374 reflections	Δρ_min = −0.53 e Å⁻³
309 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.188504 (18)	0.31643 (4)	0.04538 (2)	0.03647 (16)
Cl1	0.10243 (5)	0.11761 (11)	0.16636 (6)	0.0566 (3)
N1	0.13385 (12)	0.4848 (3)	0.01905 (15)	0.0371 (6)
N2	0.13152 (12)	0.2220 (3)	−0.03161 (14)	0.0335 (6)
O1	0.23634 (11)	0.4265 (2)	0.11935 (13)	0.0423 (6)
O2	0.23876 (10)	0.1526 (2)	0.06151 (12)	0.0384 (6)
O3	0.27110 (11)	−0.1131 (2)	0.08481 (13)	0.0454 (6)
O4	0.12199 (17)	0.2487 (3)	0.14103 (19)	0.0820 (10)
O5	0.0588 (4)	0.0750 (10)	0.1043 (5)	0.109 (4)	0.525 (13)
O6	0.0777 (7)	0.1165 (15)	0.2296 (6)	0.133 (6)	0.525 (13)
O7	0.1471 (4)	0.0082 (10)	0.1615 (7)	0.115 (5)	0.525 (13)
O5'	0.1432 (5)	0.1020 (11)	0.2320 (6)	0.116 (5)	0.475 (13)
O6'	0.1046 (7)	0.0038 (12)	0.1247 (6)	0.125 (5)	0.475 (13)
O7'	0.0456 (5)	0.1427 (13)	0.1921 (8)	0.107 (5)	0.475 (13)
C1	0.27125 (15)	0.3732 (4)	0.17002 (19)	0.0397 (8)
H1	0.2873	0.4352	0.2068	0.048*
C2	0.28934 (14)	0.2287 (4)	0.17814 (18)	0.0343 (7)
C3	0.27120 (14)	0.1246 (4)	0.12378 (17)	0.0327 (7)
C4	0.29105 (15)	−0.0172 (4)	0.13831 (17)	0.0355 (7)
C5	0.32785 (15)	−0.0494 (4)	0.20140 (19)	0.0427 (8)
H5	0.3408	−0.1427	0.2098	0.051*
C6	0.34618 (16)	0.0553 (4)	0.2532 (2)	0.0471 (9)
H6	0.3714	0.0314	0.2954	0.057*
C7	0.32762 (16)	0.1911 (4)	0.24245 (19)	0.0446 (9)
H7	0.3400	0.2601	0.2773	0.054*
C8	0.2885 (2)	−0.2566 (4)	0.0982 (2)	0.0574 (11)
H8A	0.3317	−0.2631	0.1047	0.086*
H8B	0.2727	−0.3143	0.0571	0.086*
H8C	0.2729	−0.2898	0.1417	0.086*
C9	0.13505 (17)	0.6141 (4)	0.0476 (2)	0.0461 (9)
H9	0.1648	0.6364	0.0857	0.055*
C10	0.09285 (19)	0.7191 (4)	0.0221 (2)	0.0562 (11)
H10	0.0945	0.8088	0.0436	0.067*
C11	0.04975 (18)	0.6887 (4)	−0.0340 (2)	0.0554 (11)
H11	0.0217	0.7577	−0.0511	0.067*
C12	0.04740 (16)	0.5535 (4)	−0.0665 (2)	0.0470 (9)
C13	0.09052 (14)	0.4546 (4)	−0.03700 (18)	0.0362 (8)
C14	0.08937 (15)	0.3117 (4)	−0.06422 (18)	0.0360 (8)
C15	0.04546 (16)	0.2703 (4)	−0.12121 (19)	0.0451 (9)
C16	0.04672 (17)	0.1275 (5)	−0.1436 (2)	0.0528 (10)
H16	0.0186	0.0944	−0.1811	0.063*
C17	0.08918 (18)	0.0381 (4)	−0.1103 (2)	0.0505 (9)
H17	0.0903	−0.0563	−0.1253	0.061*
C18	0.13112 (16)	0.0874 (4)	−0.05372 (19)	0.0420 (8)
H18	0.1595	0.0245	−0.0309	0.050*
C19	0.00371 (17)	0.5082 (5)	−0.1256 (2)	0.0576 (11)
H19	−0.0246	0.5732	−0.1468	0.069*
C20	0.00277 (18)	0.3747 (5)	−0.1509 (2)	0.0582 (11)
H20	−0.0265	0.3489	−0.1890	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0394 (3)	0.0299 (2)	0.0376 (2)	0.00616 (17)	−0.00553 (17)	0.00138 (18)
Cl1	0.0526 (6)	0.0501 (6)	0.0662 (7)	−0.0052 (5)	0.0029 (5)	0.0124 (5)
N1	0.0390 (15)	0.0334 (16)	0.0393 (15)	0.0047 (12)	0.0065 (13)	0.0045 (13)
N2	0.0315 (14)	0.0320 (15)	0.0366 (15)	0.0019 (11)	0.0017 (12)	0.0044 (12)
O1	0.0485 (14)	0.0300 (13)	0.0458 (14)	0.0028 (10)	−0.0058 (12)	−0.0011 (11)
O2	0.0459 (14)	0.0338 (13)	0.0321 (12)	0.0084 (10)	−0.0096 (10)	0.0003 (10)
O3	0.0582 (16)	0.0298 (13)	0.0453 (14)	0.0069 (11)	−0.0066 (12)	−0.0024 (11)
O4	0.116 (3)	0.054 (2)	0.083 (2)	−0.0084 (19)	0.041 (2)	0.0074 (18)
O5	0.086 (6)	0.104 (7)	0.124 (7)	−0.020 (5)	−0.037 (5)	0.023 (5)
O6	0.161 (17)	0.153 (11)	0.092 (8)	−0.031 (10)	0.047 (8)	0.032 (7)
O7	0.093 (7)	0.081 (6)	0.167 (12)	0.014 (5)	−0.003 (6)	0.038 (7)
O5'	0.134 (10)	0.098 (7)	0.099 (8)	0.017 (6)	−0.061 (6)	0.027 (6)
O6'	0.165 (16)	0.085 (7)	0.120 (9)	−0.016 (9)	0.001 (9)	−0.035 (7)
O7'	0.072 (7)	0.105 (7)	0.149 (13)	0.001 (5)	0.032 (6)	0.031 (8)
C1	0.0415 (19)	0.039 (2)	0.0375 (19)	−0.0060 (16)	0.0003 (16)	−0.0054 (16)
C2	0.0345 (17)	0.0327 (18)	0.0351 (17)	−0.0034 (14)	0.0017 (14)	0.0042 (14)
C3	0.0284 (16)	0.0364 (18)	0.0325 (17)	0.0007 (13)	−0.0002 (13)	0.0021 (15)
C4	0.0354 (17)	0.0359 (19)	0.0350 (18)	0.0014 (14)	0.0032 (14)	0.0034 (15)
C5	0.042 (2)	0.040 (2)	0.045 (2)	0.0049 (16)	0.0004 (16)	0.0116 (17)
C6	0.042 (2)	0.057 (2)	0.0379 (19)	−0.0005 (18)	−0.0116 (16)	0.0134 (18)
C7	0.046 (2)	0.050 (2)	0.0356 (19)	−0.0080 (17)	−0.0036 (16)	0.0003 (16)
C8	0.069 (3)	0.033 (2)	0.068 (3)	0.0084 (19)	0.000 (2)	0.001 (2)
C9	0.052 (2)	0.039 (2)	0.048 (2)	0.0036 (17)	0.0075 (17)	0.0036 (17)
C10	0.067 (3)	0.036 (2)	0.068 (3)	0.0133 (19)	0.020 (2)	0.004 (2)
C11	0.051 (2)	0.046 (2)	0.071 (3)	0.0207 (18)	0.012 (2)	0.019 (2)
C12	0.040 (2)	0.050 (2)	0.053 (2)	0.0131 (17)	0.0121 (17)	0.0177 (19)
C13	0.0325 (17)	0.041 (2)	0.0352 (17)	0.0056 (14)	0.0064 (14)	0.0131 (15)
C14	0.0327 (17)	0.041 (2)	0.0346 (17)	0.0029 (14)	0.0062 (14)	0.0078 (15)
C15	0.0359 (19)	0.057 (2)	0.041 (2)	−0.0003 (17)	0.0000 (15)	0.0052 (18)
C16	0.046 (2)	0.063 (3)	0.046 (2)	−0.0093 (19)	−0.0073 (18)	−0.002 (2)
C17	0.055 (2)	0.046 (2)	0.050 (2)	−0.0061 (18)	0.0014 (18)	−0.0046 (18)
C18	0.046 (2)	0.037 (2)	0.043 (2)	0.0028 (16)	0.0035 (16)	0.0057 (16)
C19	0.040 (2)	0.071 (3)	0.060 (3)	0.019 (2)	−0.0037 (18)	0.018 (2)
C20	0.040 (2)	0.078 (3)	0.053 (2)	0.007 (2)	−0.0105 (18)	0.007 (2)

Geometric parameters (Å, º) top

Cu1—O2	1.908 (2)	C5—H5	0.9300
Cu1—O1	1.927 (2)	C6—C7	1.349 (5)
Cu1—N2	1.995 (3)	C6—H6	0.9300
Cu1—N1	2.022 (3)	C7—H7	0.9300
Cu1—O4	2.510 (3)	C8—H8A	0.9600
Cl1—O6'	1.319 (10)	C8—H8B	0.9600
Cl1—O6	1.342 (11)	C8—H8C	0.9600
Cl1—O4	1.405 (3)	C9—C10	1.406 (5)
Cl1—O7'	1.424 (11)	C9—H9	0.9300
Cl1—O5'	1.429 (8)	C10—C11	1.355 (6)
Cl1—O7	1.442 (9)	C10—H10	0.9300
Cl1—O5	1.465 (8)	C11—C12	1.402 (6)
N1—C9	1.322 (5)	C11—H11	0.9300
N1—C13	1.357 (4)	C12—C13	1.401 (5)
N2—C18	1.329 (4)	C12—C19	1.436 (6)
N2—C14	1.350 (4)	C13—C14	1.432 (5)
O1—C1	1.246 (4)	C14—C15	1.402 (5)
O2—C3	1.305 (4)	C15—C16	1.404 (6)
O3—C4	1.368 (4)	C15—C20	1.431 (5)
O3—C8	1.417 (4)	C16—C17	1.358 (5)
C1—C2	1.419 (5)	C16—H16	0.9300
C1—H1	0.9300	C17—C18	1.393 (5)
C2—C7	1.418 (5)	C17—H17	0.9300
C2—C3	1.422 (5)	C18—H18	0.9300
C3—C4	1.420 (5)	C19—C20	1.337 (6)
C4—C5	1.372 (5)	C19—H19	0.9300
C5—C6	1.395 (5)	C20—H20	0.9300

O2—Cu1—O1	93.25 (9)	C5—C4—C3	120.6 (3)
O2—Cu1—N2	93.76 (10)	C4—C5—C6	121.1 (3)
O1—Cu1—N2	172.89 (10)	C4—C5—H5	119.4
O2—Cu1—N1	175.03 (10)	C6—C5—H5	119.4
O1—Cu1—N1	90.98 (11)	C7—C6—C5	120.5 (3)
N2—Cu1—N1	82.08 (11)	C7—C6—H6	119.7
O2—Cu1—O4	94.16 (11)	C5—C6—H6	119.7
O1—Cu1—O4	88.20 (11)	C6—C7—C2	120.1 (3)
N2—Cu1—O4	90.07 (12)	C6—C7—H7	119.9
N1—Cu1—O4	88.58 (11)	C2—C7—H7	119.9
O6'—Cl1—O6	122.8 (8)	O3—C8—H8A	109.5
O6'—Cl1—O4	119.1 (5)	O3—C8—H8B	109.5
O6—Cl1—O4	117.9 (6)	H8A—C8—H8B	109.5
O6'—Cl1—O7'	114.9 (8)	O3—C8—H8C	109.5
O6—Cl1—O7'	40.6 (6)	H8A—C8—H8C	109.5
O4—Cl1—O7'	106.8 (5)	H8B—C8—H8C	109.5
O6'—Cl1—O5'	110.0 (7)	N1—C9—C10	122.1 (4)
O6—Cl1—O5'	63.8 (8)	N1—C9—H9	118.9
O4—Cl1—O5'	100.1 (5)	C10—C9—H9	118.9
O7'—Cl1—O5'	104.0 (8)	C11—C10—C9	119.6 (4)
O6'—Cl1—O7	46.6 (6)	C11—C10—H10	120.2
O6—Cl1—O7	114.0 (8)	C9—C10—H10	120.2
O4—Cl1—O7	111.2 (4)	C10—C11—C12	120.1 (3)
O7'—Cl1—O7	141.9 (6)	C10—C11—H11	119.9
O5'—Cl1—O7	66.6 (6)	C12—C11—H11	119.9
O6'—Cl1—O5	52.7 (6)	C13—C12—C11	116.6 (4)
O6—Cl1—O5	111.5 (7)	C13—C12—C19	118.0 (4)
O4—Cl1—O5	100.8 (4)	C11—C12—C19	125.3 (4)
O7'—Cl1—O5	76.5 (7)	N1—C13—C12	123.4 (3)
O5'—Cl1—O5	157.9 (5)	N1—C13—C14	116.3 (3)
O7—Cl1—O5	99.1 (7)	C12—C13—C14	120.3 (3)
C9—N1—C13	118.2 (3)	N2—C14—C15	123.2 (3)
C9—N1—Cu1	129.9 (3)	N2—C14—C13	116.6 (3)
C13—N1—Cu1	111.9 (2)	C15—C14—C13	120.2 (3)
C18—N2—C14	118.7 (3)	C14—C15—C16	116.6 (3)
C18—N2—Cu1	128.4 (2)	C14—C15—C20	118.1 (4)
C14—N2—Cu1	112.9 (2)	C16—C15—C20	125.4 (4)
C1—O1—Cu1	123.8 (2)	C17—C16—C15	119.8 (3)
C3—O2—Cu1	123.7 (2)	C17—C16—H16	120.1
C4—O3—C8	116.3 (3)	C15—C16—H16	120.1
Cl1—O4—Cu1	133.3 (2)	C16—C17—C18	120.2 (4)
O1—C1—C2	127.5 (3)	C16—C17—H17	119.9
O1—C1—H1	116.3	C18—C17—H17	119.9
C2—C1—H1	116.3	N2—C18—C17	121.6 (3)
C7—C2—C1	117.5 (3)	N2—C18—H18	119.2
C7—C2—C3	120.4 (3)	C17—C18—H18	119.2
C1—C2—C3	122.1 (3)	C20—C19—C12	121.5 (4)
O2—C3—C4	118.8 (3)	C20—C19—H19	119.3
O2—C3—C2	123.9 (3)	C12—C19—H19	119.3
C4—C3—C2	117.2 (3)	C19—C20—C15	121.9 (4)
O3—C4—C5	124.9 (3)	C19—C20—H20	119.0
O3—C4—C3	114.6 (3)	C15—C20—H20	119.0

Experimental details

Crystal data
Chemical formula	[Cu(C₈H₇O₃)(ClO₄)(C₁₂H₈N₂)]
M_r	494.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	22.332 (2), 9.3986 (9), 18.339 (2)
β (°)	96.733 (2)
V (Å³)	3822.7 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.33
Crystal size (mm)	0.26 × 0.17 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.723, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	9561, 3374, 2731
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.109, 1.01
No. of reflections	3374
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.53

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the National Natural Science Foundation of China (grant No. 20471056) and the PhD Program Foundation of the Ministry of Education of China (grant No. 20060423005).

References

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