{μ-6,6′-Dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato-1κ4O6,O1,O1′,O6′:2κ4O1,N,N′,O1′}(methanol-1κO)(perchlorato-1κO)copper(II)sodium(I)

Xiao, H.-Q.; Zhang, H.

doi:10.1107/S1600536809010356

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m445

doi:10.1107/S1600536809010356

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{μ-6,6′-Dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1κ⁴O⁶,O¹,O^1′,O^6′:2κ⁴O¹,N,N′,O^1′}(methanol-1κO)(perchlorato-1κO)copper(II)sodium(I)

Hui-Quan Xiao ^a and Hua Zhang ^b ^*

^aDepartment of Chemistry, Shaoxing University, Shaoxing 312000, People's Republic of China, and ^bCollege of Chemical Engineering and Materials, Heilongjiang University, Haerbin 150080, People's Republic of China
^*Correspondence e-mail: chemreagent@yahoo.cn

(Received 28 February 2009; accepted 20 March 2009; online 25 March 2009)

The molecule of the title compound, [CuNa(C₁₈H₁₈N₂O₄)(ClO₄)(CH₃OH)], is almost planar with mean deviation of 5.2 (8)°. The coordination environment of the Cu^II ion is distorted square-planar and it is N₂O₂-chelated by the 6,6′-dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolate Schiff base ligand. The Na atom is chelated by the four O atoms of the Schiff base ligand, and coordinated by a methanol molecule and a perchlorate anion. The six-coordinate Na atom adopts a distorted octahedral coordination geometry. The O atoms of the perchlorate anion are disordered over two sites with site-occupancy factors of 0.697 (5) and 0.303 (5). O—H⋯O hydrogen bonding occurs.

Related literature

For chemical background, see: Lindoy et al. (1976 ). For related structures, see: Correia et al. (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[CuNa(C₁₈H₁₈N₂O₄)(ClO₄)(CH₄O)]
M_r = 544.38
Monoclinic, P 2₁ /n
a = 12.030 (2) Å
b = 8.1444 (14) Å
c = 23.381 (4) Å
β = 104.273 (3)°
V = 2220.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 273 K
0.17 × 0.15 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.825, T_max = 0.881
10424 measured reflections
3843 independent reflections
2651 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.131
S = 1.03
3843 reflections
339 parameters
148 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9A⋯O7ⁱ	0.82	2.11	2.912 (8)	164
O9—H9A⋯O5′ⁱ	0.82	1.99	2.761 (13)	156
O9—H9A⋯O5′ⁱ	0.82	1.99	2.761 (13)	156
O9—H9A⋯O7ⁱ	0.82	2.11	2.912 (8)	164
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010356/pv2143sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010356/pv2143Isup2.hkl

checkCIF report

Comment top

The schiff bases have been known as effective ligands for metal ions and used in the mechanism of many biochemical processes (Lindoy et al., 1976). N,N-Disalicylideneethylenediamine type schiff bases present versatile steric, electronic and lipophilic properties. The synthesis, characterization and solution studies of N,N'-disalicylideneethylenediamine type complexes have been reported recently (Correia et al., 2005). We report here the synthesis and crystal structure of the title compound, (I). The molecular structure of (I) is shown in Fig. 1. The values of the geometric parameters in (I) are normal (Allen et al., 1987). Cu(II) and Na(I) are connected via two bridging oxygen atoms of the ligand. The coordination environment of the Cu²⁺ ion is distorted square-planar and it is coordinated by N₂O₂ of the Schiff base ligand. The Na atom is chelated by the four O atoms of the 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol ligand, a methanol and a perchlorate anion. The six-coordinate Na atom adopts a distorted octahedral coordination geometry.

Related literature top

For chemical background, see: Lindoy et al. (1976). For related structures, see: Correia et al. (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol (1 mmol) and copper chloride (1 mmol) in absolute ethanol (15 ml) was stirred for 30 min and sodium perchlorate (1 mmol) was added, stirred for another 15 min and then filtered. The resulting clear orange solution was allowed to evaporate at room temperature for 7 days, after which large orange block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

{µ-6,6'-Dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato- 1κ⁴O⁶,O¹,O^1',O^6': 2κ⁴O¹,N,N',O^1'}(methanol-1κO)(perchlorato- 1κO)copper(II)sodium(I) top

Crystal data top

[CuNa(C₁₈H₁₈N₂O₄)(ClO₄)(CH₄O)]	F(000) = 1116
M_r = 544.38	D_x = 1.629 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2083 reflections
a = 12.030 (2) Å	θ = 2.7–21.2°
b = 8.1444 (14) Å	µ = 1.18 mm⁻¹
c = 23.381 (4) Å	T = 273 K
β = 104.273 (3)°	Block, blue
V = 2220.1 (7) Å³	0.17 × 0.15 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3843 independent reflections
Radiation source: fine-focus sealed tube	2651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→10
T_min = 0.825, T_max = 0.881	k = −9→9
10424 measured reflections	l = −27→26

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0701P)² + 0.3025P] where P = (F_o² + 2F_c²)/3
3843 reflections	(Δ/σ)_max = 0.002
339 parameters	Δρ_max = 0.56 e Å⁻³
148 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

[CuNa(C₁₈H₁₈N₂O₄)(ClO₄)(CH₄O)]	V = 2220.1 (7) Å³
M_r = 544.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.030 (2) Å	µ = 1.18 mm⁻¹
b = 8.1444 (14) Å	T = 273 K
c = 23.381 (4) Å	0.17 × 0.15 × 0.11 mm
β = 104.273 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3843 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2651 reflections with I > 2σ(I)
T_min = 0.825, T_max = 0.881	R_int = 0.039
10424 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	148 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.03	Δρ_max = 0.56 e Å⁻³
3843 reflections	Δρ_min = −0.68 e Å⁻³
339 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	0.67526 (4)	0.41736 (7)	1.00850 (2)	0.0401 (2)
Cl1	0.50250 (12)	0.6363 (2)	0.73548 (7)	0.0739 (4)
Na1	0.64991 (14)	0.4180 (2)	0.86447 (7)	0.0487 (5)
O1	0.7475 (2)	0.5185 (4)	0.95491 (12)	0.0450 (7)
O2	0.5730 (2)	0.3261 (4)	0.94164 (12)	0.0469 (8)
O3	0.8214 (3)	0.6120 (4)	0.86695 (14)	0.0586 (9)
O4	0.4620 (3)	0.2267 (4)	0.83993 (13)	0.0551 (8)
O5	0.4054 (5)	0.7314 (9)	0.7368 (3)	0.0941 (18)	0.697 (5)
O6	0.5622 (6)	0.5794 (11)	0.7907 (3)	0.107 (2)	0.697 (5)
O7	0.5660 (5)	0.7560 (8)	0.7127 (3)	0.1002 (19)	0.697 (5)
O8	0.4583 (6)	0.5066 (8)	0.6955 (3)	0.121 (2)	0.697 (5)
O5'	0.5499 (13)	0.648 (2)	0.6860 (5)	0.102 (3)	0.303 (5)
O6'	0.5809 (11)	0.5076 (15)	0.7574 (8)	0.095 (3)	0.303 (5)
O7'	0.3899 (7)	0.596 (2)	0.7381 (8)	0.106 (3)	0.303 (5)
O8'	0.5499 (14)	0.683 (2)	0.7956 (3)	0.100 (3)	0.303 (5)
O9	0.7367 (4)	0.1937 (5)	0.8355 (2)	0.0792 (12)
H9A	0.7905	0.1921	0.8198	0.119*
N1	0.7854 (3)	0.4916 (5)	1.07680 (15)	0.0450 (9)
N2	0.5934 (3)	0.3323 (5)	1.06299 (15)	0.0461 (9)
C1	0.9026 (4)	0.6473 (5)	1.0254 (2)	0.0438 (11)
C2	0.8414 (3)	0.6065 (5)	0.9680 (2)	0.0400 (10)
C3	0.8843 (4)	0.6644 (5)	0.92130 (19)	0.0433 (11)
C4	0.9803 (4)	0.7612 (6)	0.9308 (2)	0.0533 (12)
H4	1.0059	0.7997	0.8988	0.064*
C5	1.0398 (4)	0.8024 (6)	0.9880 (3)	0.0583 (13)
H5	1.1046	0.8689	0.9944	0.070*
C6	1.0018 (4)	0.7438 (6)	1.0342 (2)	0.0549 (12)
H6	1.0424	0.7684	1.0725	0.066*
C7	0.8704 (4)	0.5871 (6)	1.0767 (2)	0.0476 (11)
H7	0.9152	0.6201	1.1132	0.057*
C8	0.8646 (5)	0.6465 (8)	0.8172 (2)	0.0694 (15)
H8A	0.8684	0.7632	0.8122	0.104*
H8B	0.8147	0.5994	0.7826	0.104*
H8C	0.9399	0.6003	0.8229	0.104*
C9	0.4421 (4)	0.1995 (5)	0.9915 (2)	0.0449 (11)
C10	0.4820 (4)	0.2381 (5)	0.94127 (19)	0.0404 (10)
C11	0.4171 (4)	0.1799 (6)	0.8863 (2)	0.0455 (11)
C12	0.3175 (4)	0.0908 (6)	0.8808 (2)	0.0559 (13)
H12	0.2759	0.0549	0.8440	0.067*
C13	0.2806 (4)	0.0556 (6)	0.9310 (3)	0.0639 (15)
H13	0.2136	−0.0043	0.9278	0.077*
C14	0.3411 (4)	0.1075 (6)	0.9848 (2)	0.0545 (13)
H14	0.3151	0.0814	1.0180	0.065*
C15	0.5014 (4)	0.2496 (6)	1.0498 (2)	0.0501 (12)
H15	0.4695	0.2188	1.0806	0.060*
C16	0.4046 (5)	0.1701 (8)	0.7830 (2)	0.0810 (18)
H16A	0.4001	0.0525	0.7833	0.122*
H16B	0.4462	0.2042	0.7549	0.122*
H16C	0.3286	0.2154	0.7723	0.122*
C17	0.7679 (5)	0.4219 (7)	1.1319 (2)	0.0614 (14)
H17A	0.7920	0.5000	1.1639	0.074*
H17B	0.8132	0.3227	1.1420	0.074*
C18	0.6426 (5)	0.3831 (7)	1.1231 (2)	0.0619 (14)
H18A	0.6334	0.2961	1.1499	0.074*
H18B	0.6026	0.4795	1.1320	0.074*
C19	0.7189 (7)	0.0396 (9)	0.8542 (3)	0.107 (2)
H19A	0.6615	0.0434	0.8763	0.161*
H19B	0.7892	−0.0022	0.8788	0.161*
H19C	0.6935	−0.0309	0.8206	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0401 (3)	0.0532 (4)	0.0286 (3)	0.0046 (2)	0.0112 (2)	0.0037 (2)
Cl1	0.0659 (9)	0.0907 (10)	0.0711 (9)	0.0173 (7)	0.0283 (7)	0.0296 (8)
Na1	0.0491 (10)	0.0658 (12)	0.0315 (9)	0.0029 (8)	0.0108 (8)	0.0001 (8)
O1	0.0392 (17)	0.066 (2)	0.0297 (16)	−0.0046 (15)	0.0077 (13)	0.0015 (14)
O2	0.0442 (18)	0.067 (2)	0.0328 (17)	−0.0092 (15)	0.0147 (14)	0.0002 (14)
O3	0.0522 (19)	0.089 (3)	0.0370 (19)	−0.0065 (17)	0.0157 (15)	0.0078 (17)
O4	0.0504 (19)	0.079 (2)	0.0386 (18)	−0.0120 (16)	0.0158 (15)	−0.0082 (16)
O5	0.082 (3)	0.100 (3)	0.099 (3)	0.023 (3)	0.022 (3)	0.000 (3)
O6	0.103 (3)	0.110 (3)	0.099 (3)	0.015 (3)	0.011 (3)	0.029 (3)
O7	0.100 (3)	0.105 (3)	0.102 (3)	−0.007 (3)	0.038 (3)	0.024 (3)
O8	0.122 (3)	0.114 (3)	0.119 (3)	0.012 (3)	0.014 (3)	−0.007 (3)
O5'	0.101 (4)	0.110 (4)	0.099 (4)	0.005 (3)	0.030 (3)	0.008 (3)
O6'	0.094 (4)	0.096 (4)	0.093 (4)	0.009 (4)	0.019 (4)	0.013 (4)
O7'	0.098 (4)	0.114 (4)	0.105 (4)	0.006 (3)	0.022 (3)	0.008 (4)
O8'	0.096 (4)	0.101 (4)	0.101 (4)	0.007 (4)	0.018 (4)	0.016 (4)
O9	0.084 (3)	0.082 (3)	0.080 (3)	0.017 (2)	0.038 (2)	−0.005 (2)
N1	0.052 (2)	0.057 (2)	0.0242 (19)	0.010 (2)	0.0073 (16)	0.0034 (17)
N2	0.055 (2)	0.053 (2)	0.033 (2)	0.0042 (19)	0.0157 (18)	0.0058 (17)
C1	0.044 (3)	0.044 (3)	0.042 (3)	0.008 (2)	0.007 (2)	−0.004 (2)
C2	0.033 (2)	0.044 (3)	0.044 (3)	0.0067 (19)	0.0110 (19)	0.000 (2)
C3	0.042 (3)	0.048 (3)	0.042 (3)	0.008 (2)	0.015 (2)	0.007 (2)
C4	0.052 (3)	0.051 (3)	0.063 (3)	0.001 (2)	0.023 (2)	0.009 (2)
C5	0.055 (3)	0.046 (3)	0.073 (4)	−0.007 (2)	0.014 (3)	−0.004 (3)
C6	0.050 (3)	0.050 (3)	0.061 (3)	−0.003 (2)	0.006 (2)	−0.011 (2)
C7	0.048 (3)	0.052 (3)	0.039 (3)	0.009 (2)	0.002 (2)	−0.004 (2)
C8	0.073 (4)	0.098 (4)	0.043 (3)	0.000 (3)	0.025 (3)	0.015 (3)
C9	0.047 (3)	0.046 (3)	0.047 (3)	0.012 (2)	0.023 (2)	0.009 (2)
C10	0.038 (2)	0.042 (3)	0.043 (3)	0.0073 (19)	0.015 (2)	0.004 (2)
C11	0.042 (3)	0.049 (3)	0.049 (3)	0.002 (2)	0.016 (2)	−0.002 (2)
C12	0.044 (3)	0.059 (3)	0.063 (3)	−0.003 (2)	0.011 (2)	−0.004 (3)
C13	0.048 (3)	0.062 (3)	0.088 (5)	−0.008 (2)	0.030 (3)	0.003 (3)
C14	0.051 (3)	0.052 (3)	0.071 (4)	0.005 (2)	0.036 (3)	0.013 (3)
C15	0.059 (3)	0.050 (3)	0.049 (3)	0.013 (2)	0.028 (2)	0.014 (2)
C16	0.080 (4)	0.117 (5)	0.046 (3)	−0.026 (4)	0.015 (3)	−0.022 (3)
C17	0.068 (3)	0.083 (4)	0.030 (3)	0.007 (3)	0.006 (2)	0.005 (2)
C18	0.087 (4)	0.068 (4)	0.037 (3)	0.002 (3)	0.026 (3)	0.004 (2)
C19	0.127 (6)	0.090 (5)	0.110 (6)	0.039 (5)	0.038 (5)	0.022 (5)

Geometric parameters (Å, º) top

Cu1—O1	1.881 (3)	C4—H4	0.9300
Cu1—O2	1.887 (3)	C5—C6	1.360 (7)
Cu1—N1	1.905 (4)	C5—H5	0.9300
Cu1—N2	1.922 (4)	C6—H6	0.9300
Cl1—O6	1.394 (4)	C7—H7	0.9300
Cl1—O5	1.408 (4)	C8—H8A	0.9600
Cl1—O7'	1.410 (5)	C8—H8B	0.9600
Cl1—O5'	1.413 (5)	C8—H8C	0.9600
Cl1—O6'	1.418 (5)	C9—C14	1.403 (6)
Cl1—O7	1.421 (4)	C9—C10	1.410 (6)
Cl1—O8	1.424 (5)	C9—C15	1.432 (7)
Cl1—O8'	1.432 (5)	C10—C11	1.411 (6)
O1—C2	1.309 (5)	C11—C12	1.380 (6)
O2—C10	1.308 (5)	C12—C13	1.382 (7)
O3—C3	1.377 (5)	C12—H12	0.9300
O3—C8	1.415 (5)	C13—C14	1.357 (7)
O4—C11	1.378 (5)	C13—H13	0.9300
O4—C16	1.417 (6)	C14—H14	0.9300
O9—C19	1.362 (8)	C15—H15	0.9300
O9—H9A	0.8200	C16—H16A	0.9600
N1—C7	1.285 (6)	C16—H16B	0.9600
N1—C17	1.470 (6)	C16—H16C	0.9600
N2—C15	1.267 (6)	C17—C18	1.504 (7)
N2—C18	1.444 (6)	C17—H17A	0.9700
C1—C6	1.400 (7)	C17—H17B	0.9700
C1—C2	1.402 (6)	C18—H18A	0.9700
C1—C7	1.435 (6)	C18—H18B	0.9700
C2—C3	1.400 (6)	C19—H19A	0.9600
C3—C4	1.370 (6)	C19—H19B	0.9600
C4—C5	1.393 (7)	C19—H19C	0.9600

O1—Cu1—O2	86.23 (12)	O3—C8—H8B	109.5
O1—Cu1—N1	94.56 (15)	H8A—C8—H8B	109.5
O2—Cu1—N1	174.99 (15)	O3—C8—H8C	109.5
O1—Cu1—N2	174.73 (15)	H8A—C8—H8C	109.5
O2—Cu1—N2	94.09 (15)	H8B—C8—H8C	109.5
N1—Cu1—N2	85.58 (16)	C14—C9—C10	119.2 (4)
O6—Cl1—O5	113.8 (5)	C14—C9—C15	118.2 (4)
O7'—Cl1—O5'	129.6 (11)	C10—C9—C15	122.5 (4)
O7'—Cl1—O6'	111.9 (10)	O2—C10—C9	125.0 (4)
O5'—Cl1—O6'	88.9 (10)	O2—C10—C11	117.6 (4)
O6—Cl1—O7	112.0 (5)	C9—C10—C11	117.4 (4)
O5—Cl1—O7	99.0 (5)	O4—C11—C12	124.9 (4)
O6—Cl1—O8	112.6 (5)	O4—C11—C10	112.8 (4)
O5—Cl1—O8	104.2 (4)	C12—C11—C10	122.2 (4)
O7—Cl1—O8	114.3 (5)	C11—C12—C13	118.9 (5)
O7'—Cl1—O8'	100.0 (10)	C11—C12—H12	120.5
O5'—Cl1—O8'	129.9 (11)	C13—C12—H12	120.5
O6'—Cl1—O8'	76.9 (10)	C14—C13—C12	120.8 (5)
C2—O1—Cu1	126.7 (3)	C14—C13—H13	119.6
C10—O2—Cu1	126.5 (3)	C12—C13—H13	119.6
C3—O3—C8	117.9 (4)	C13—C14—C9	121.5 (4)
C11—O4—C16	117.0 (4)	C13—C14—H14	119.3
C19—O9—H9A	109.5	C9—C14—H14	119.3
C7—N1—C17	121.4 (4)	N2—C15—C9	125.7 (4)
C7—N1—Cu1	125.4 (3)	N2—C15—H15	117.2
C17—N1—Cu1	113.1 (3)	C9—C15—H15	117.2
C15—N2—C18	120.9 (4)	O4—C16—H16A	109.5
C15—N2—Cu1	126.2 (3)	O4—C16—H16B	109.5
C18—N2—Cu1	112.8 (3)	H16A—C16—H16B	109.5
C6—C1—C2	120.1 (4)	O4—C16—H16C	109.5
C6—C1—C7	117.7 (4)	H16A—C16—H16C	109.5
C2—C1—C7	122.2 (4)	H16B—C16—H16C	109.5
O1—C2—C3	117.7 (4)	N1—C17—C18	108.4 (4)
O1—C2—C1	125.0 (4)	N1—C17—H17A	110.0
C3—C2—C1	117.3 (4)	C18—C17—H17A	110.0
C4—C3—O3	125.3 (4)	N1—C17—H17B	110.0
C4—C3—C2	121.7 (4)	C18—C17—H17B	110.0
O3—C3—C2	113.0 (4)	H17A—C17—H17B	108.4
C3—C4—C5	120.4 (5)	N2—C18—C17	110.5 (4)
C3—C4—H4	119.8	N2—C18—H18A	109.5
C5—C4—H4	119.8	C17—C18—H18A	109.5
C6—C5—C4	119.0 (5)	N2—C18—H18B	109.5
C6—C5—H5	120.5	C17—C18—H18B	109.5
C4—C5—H5	120.5	H18A—C18—H18B	108.1
C5—C6—C1	121.4 (5)	O9—C19—H19A	109.5
C5—C6—H6	119.3	O9—C19—H19B	109.5
C1—C6—H6	119.3	H19A—C19—H19B	109.5
N1—C7—C1	126.0 (4)	O9—C19—H19C	109.5
N1—C7—H7	117.0	H19A—C19—H19C	109.5
C1—C7—H7	117.0	H19B—C19—H19C	109.5
O3—C8—H8A	109.5

O2—Cu1—O1—C2	−175.3 (3)	C2—C1—C6—C5	1.2 (7)
N1—Cu1—O1—C2	−0.2 (3)	C7—C1—C6—C5	178.4 (4)
N2—Cu1—O1—C2	91.1 (16)	C17—N1—C7—C1	172.8 (4)
O1—Cu1—O2—C10	−174.8 (4)	Cu1—N1—C7—C1	−4.1 (7)
N1—Cu1—O2—C10	86.0 (17)	C6—C1—C7—N1	−176.8 (4)
N2—Cu1—O2—C10	0.0 (4)	C2—C1—C7—N1	0.3 (7)
O1—Cu1—N1—C7	3.7 (4)	Cu1—O2—C10—C9	1.9 (6)
O2—Cu1—N1—C7	102.6 (16)	Cu1—O2—C10—C11	−179.5 (3)
N2—Cu1—N1—C7	−171.1 (4)	C14—C9—C10—O2	178.3 (4)
O1—Cu1—N1—C17	−173.5 (3)	C15—C9—C10—O2	−2.3 (7)
O2—Cu1—N1—C17	−74.6 (17)	C14—C9—C10—C11	−0.4 (6)
N2—Cu1—N1—C17	11.8 (3)	C15—C9—C10—C11	179.1 (4)
O1—Cu1—N2—C15	91.5 (16)	C16—O4—C11—C12	−3.9 (7)
O2—Cu1—N2—C15	−1.8 (4)	C16—O4—C11—C10	178.3 (4)
N1—Cu1—N2—C15	−176.8 (4)	O2—C10—C11—O4	0.1 (6)
O1—Cu1—N2—C18	−83.8 (16)	C9—C10—C11—O4	178.8 (4)
O2—Cu1—N2—C18	−177.1 (3)	O2—C10—C11—C12	−177.8 (4)
N1—Cu1—N2—C18	7.9 (3)	C9—C10—C11—C12	1.0 (7)
Cu1—O1—C2—C3	176.9 (3)	O4—C11—C12—C13	−178.4 (4)
Cu1—O1—C2—C1	−3.1 (6)	C10—C11—C12—C13	−0.8 (7)
C6—C1—C2—O1	−179.4 (4)	C11—C12—C13—C14	0.0 (8)
C7—C1—C2—O1	3.6 (7)	C12—C13—C14—C9	0.6 (8)
C6—C1—C2—C3	0.7 (6)	C10—C9—C14—C13	−0.4 (7)
C7—C1—C2—C3	−176.4 (4)	C15—C9—C14—C13	−179.9 (4)
C8—O3—C3—C4	6.6 (7)	C18—N2—C15—C9	176.8 (4)
C8—O3—C3—C2	−172.6 (4)	Cu1—N2—C15—C9	1.9 (7)
O1—C2—C3—C4	178.1 (4)	C14—C9—C15—N2	179.7 (4)
C1—C2—C3—C4	−1.9 (6)	C10—C9—C15—N2	0.2 (7)
O1—C2—C3—O3	−2.7 (6)	C7—N1—C17—C18	154.9 (4)
C1—C2—C3—O3	177.3 (4)	Cu1—N1—C17—C18	−27.8 (5)
O3—C3—C4—C5	−177.8 (4)	C15—N2—C18—C17	159.2 (4)
C2—C3—C4—C5	1.3 (7)	Cu1—N2—C18—C17	−25.3 (5)
C3—C4—C5—C6	0.6 (7)	N1—C17—C18—N2	33.7 (6)
C4—C5—C6—C1	−1.8 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O7ⁱ	0.82	2.11	2.912 (8)	164
O9—H9A···O5′ⁱ	0.82	1.99	2.761 (13)	156
O9—H9A···O5′ⁱ	0.82	1.99	2.761 (13)	156
O9—H9A···O7ⁱ	0.82	2.11	2.912 (8)	164

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[CuNa(C₁₈H₁₈N₂O₄)(ClO₄)(CH₄O)]
M_r	544.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	12.030 (2), 8.1444 (14), 23.381 (4)
β (°)	104.273 (3)
V (Å³)	2220.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.17 × 0.15 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.825, 0.881
No. of measured, independent and observed [I > 2σ(I)] reflections	10424, 3843, 2651
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.131, 1.03
No. of reflections	3843
No. of parameters	339
No. of restraints	148
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.68

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O7ⁱ	0.82	2.11	2.912 (8)	164.1
O9—H9A···O5'ⁱ	0.82	1.99	2.761 (13)	156.2
O9—H9A···O5'ⁱ	0.82	1.99	2.761 (13)	156.2
O9—H9A···O7ⁱ	0.82	2.11	2.912 (8)	164.1

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation (Y4080481).

References

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