[N,N′-Bis(6-methoxy­salicyl­idene)-1,3-di­amino­propane]copper(II)

Habibi, M.H.; Mokhtari, R.; Harrington, R.W.; Clegg, W.

doi:10.1107/S1600536807030723

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[N,N'-Bis(6-methoxysalicylidene)-1,3-diaminopropane]copper(II)

M. H. Habibi, R. Mokhtari, R. W. Harrington and W. Clegg

The title compound, [Cu(C₁₉H₂₀N₂O₄)], is a mononuclear copper(II) Schiff base complex. The Cu^II ion is surrounded by two imine N and two phenolate O atoms of the tetradentate ligand in a square-planar coordination with a slight tetrahedral distortion. The dihedral angle between the CuN₂ and CuO₂ planes is 25.07 (9)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030723/wm2129sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030723/wm2129Isup2.hkl Contains datablock I

CCDC reference: 654824

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R factor = 0.023
wR factor = 0.063
Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.33
           From the CIF: _reflns_number_total               4157
           Count of symmetry unique reflns         2303
           Completeness (_total/calc)            180.50%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1854
           Fraction of Friedel pairs measured     0.805
           Are heavy atom types Z>Si present        yes
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu          (2)       2.22
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Metal derivatives of Schiff bases have been studied extensively, and Cu^II and Ni^II complexes play a major role in both synthetic and structural research. The coordination of the metal cations is usually planar in the case of Ni, but for Cu a tetrahedral distortion is often observed (Garnovskii et al., 1993). We report here the results of the reaction of Cu^II with the tetradentate ligand N,N'-bis(6-methoxysalicylidene)-1,3-diaminopropane in a 1:1 molar ratio, forming the title compound, (I).

A view of the molecular structure of (I) is shown in Fig. 1. The crystal structure of the ligand (but without methoxy substituents) is known for a long time (Elerman et al., 1991), as are about 150 of its metal complexes (found in a search of the Cambridge Structural Database [version 5.28] plus two updates until May 2007; Allen, 2002). Structures of the Cu^II complex which are comparable with the title compound have been reported several times, the most recent given by Nathan et al. (2003). The title complex, however, is the first reported example of a Schiff base, as a ligand or uncomplexed, in which substituents in the 6 position of the benzene rings are present.

The Cu^II coordination polyhedron is approximately square planar, with a significant distortion towards tetrahedral, as indicated by the dihedral angle of 25.07 (9)° between the CuO₂ and CuN₂ planes. This, and the Cu—O and Cu—N distances (see Table), are similar to those observed in other Cu^II complexes of related Schiff bases.

Related literature top

A review on ligand environments and structures of Schiff base adducts and tetracoordinated metal chelates has been given by Garnovskii et al. (1993). The Cambridge Structural Database (Version 5.28, plus two updates until May 2007; Allen, 2002) was used as a source for searching for related structures. For comparable Schiff base complexes, see: Elerman et al. (1991); Nathan et al. (2003).

Experimental top

A mixture of 6-methoxysalicylaldehyde (2.0 mmol, 304 mg) and 1,3-diaminopropane (1.0 mmol, 74 mg) was dissolved in methanol (10 ml) with stirring for 30 min at room temperature, to give a clear yellow solution. A methanol solution (10 ml) of Cu(CH₃COO)₂^.2H₂O (1.0 mmol, 218 mg) was then added. The mixture was stirred for further 30 min and then filtered. After keeping the filtrate in air for 7 d, blue block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent, in about 65% yield.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2005b); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: SHELXTL and local programs.

Figures top

Fig. 1. The molecular structure with atom labels, drawn with ellipsoids at the 50% probability level for all non-H atoms. H atoms are given as spheres of arbitrary radius.

{2,2'-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato}copper(II) top

Crystal data top

[Cu(C₁₉H₂₀N₂O₄)]	F(000) = 836
M_r = 403.91	D_x = 1.542 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 9351 reflections
a = 13.7911 (14) Å	θ = 2.2–28.3°
b = 12.7032 (13) Å	µ = 1.28 mm⁻¹
c = 9.9329 (10) Å	T = 150 K
V = 1740.2 (3) Å³	Block, blue
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART 1K CCD diffractometer	4157 independent reflections
Radiation source: fine-focus sealed tube	3766 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2005a)	h = −17→17
T_min = 0.700, T_max = 0.785	k = −16→16
14731 measured reflections	l = −13→13

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)] = 0.024	H-atom parameters constrained
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.0332P)² + 0.2389P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4157 reflections	Δρ_max = 0.33 e Å⁻³
237 parameters	Δρ_min = −0.44 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1916 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.013 (12)

Crystal data top

[Cu(C₁₉H₂₀N₂O₄)]	V = 1740.2 (3) Å³
M_r = 403.91	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 13.7911 (14) Å	µ = 1.28 mm⁻¹
b = 12.7032 (13) Å	T = 150 K
c = 9.9329 (10) Å	0.30 × 0.30 × 0.20 mm

Data collection top

Bruker SMART 1K CCD diffractometer	4157 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2005a)	3766 reflections with I > 2σ(I)
T_min = 0.700, T_max = 0.785	R_int = 0.028
14731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.063	Δρ_max = 0.33 e Å⁻³
S = 1.04	Δρ_min = −0.44 e Å⁻³
4157 reflections	Absolute structure: Flack (1983), 1916 Friedel pairs
237 parameters	Absolute structure parameter: 0.013 (12)
1 restraint

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.

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

	x	y	z	U_iso*/U_eq
Cu	0.174992 (13)	0.252482 (15)	0.36441 (5)	0.01625 (6)
N1	0.23946 (12)	0.12304 (12)	0.42218 (15)	0.0194 (3)
N2	0.28978 (10)	0.32088 (11)	0.28765 (16)	0.0171 (3)
O1	0.13783 (12)	−0.12408 (11)	0.62238 (16)	0.0321 (3)
O2	0.06371 (10)	0.22063 (11)	0.47204 (15)	0.0239 (3)
O3	0.08904 (9)	0.34212 (10)	0.26854 (13)	0.0210 (3)
O4	0.30881 (10)	0.53932 (12)	0.00073 (16)	0.0298 (3)
C1	0.1202 (2)	−0.20841 (18)	0.7155 (3)	0.0402 (6)
H1A	0.1723	−0.2605	0.7085	0.060*
H1B	0.0580	−0.2419	0.6942	0.060*
H1C	0.1181	−0.1803	0.8074	0.060*
C2	0.07334 (16)	−0.04266 (15)	0.6220 (2)	0.0244 (4)
C3	−0.01325 (16)	−0.04319 (16)	0.6918 (2)	0.0284 (5)
H3A	−0.0321	−0.1025	0.7438	0.034*
C4	−0.07236 (16)	0.04570 (17)	0.6838 (2)	0.0292 (4)
H4A	−0.1319	0.0460	0.7320	0.035*
C5	−0.04815 (15)	0.13287 (16)	0.6092 (2)	0.0258 (4)
H5A	−0.0913	0.1911	0.6052	0.031*
C6	0.04105 (14)	0.13626 (15)	0.53826 (18)	0.0208 (4)
C7	0.10334 (15)	0.04696 (15)	0.54488 (19)	0.0205 (4)
C8	0.19971 (14)	0.04821 (15)	0.49065 (19)	0.0210 (4)
H8A	0.2384	−0.0124	0.5068	0.025*
C9	0.34254 (14)	0.11051 (14)	0.38763 (19)	0.0221 (4)
H9A	0.3495	0.1006	0.2892	0.027*
H9B	0.3691	0.0475	0.4332	0.027*
C10	0.39877 (15)	0.20812 (16)	0.4319 (2)	0.0227 (4)
H10A	0.3736	0.2323	0.5199	0.027*
H10B	0.4679	0.1893	0.4439	0.027*
C11	0.39108 (13)	0.29754 (15)	0.33088 (19)	0.0207 (4)
H11A	0.4194	0.3618	0.3712	0.025*
H11B	0.4300	0.2795	0.2504	0.025*
C12	0.28636 (14)	0.39154 (14)	0.19369 (18)	0.0182 (4)
H12A	0.3471	0.4145	0.1595	0.022*
C13	0.20214 (13)	0.43938 (14)	0.13492 (18)	0.0178 (4)
C14	0.21461 (13)	0.51992 (15)	0.03636 (19)	0.0204 (4)
C15	0.13649 (14)	0.57306 (15)	−0.0176 (2)	0.0226 (4)
H15A	0.1456	0.6263	−0.0835	0.027*
C16	0.04276 (14)	0.54632 (15)	0.0277 (2)	0.0241 (4)
H16A	−0.0116	0.5824	−0.0087	0.029*
C17	0.02793 (14)	0.46998 (15)	0.1223 (2)	0.0226 (4)
H17A	−0.0363	0.4541	0.1503	0.027*
C18	0.10671 (13)	0.41422 (14)	0.17916 (19)	0.0184 (4)
C19	0.32782 (15)	0.62249 (17)	−0.0922 (2)	0.0295 (5)
H19A	0.3979	0.6284	−0.1068	0.044*
H19B	0.3030	0.6889	−0.0556	0.044*
H19C	0.2956	0.6073	−0.1780	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.01746 (10)	0.01431 (10)	0.01697 (10)	0.00117 (8)	0.00155 (11)	0.00191 (8)
N1	0.0246 (8)	0.0166 (7)	0.0170 (7)	0.0037 (6)	0.0008 (6)	−0.0003 (6)
N2	0.0165 (7)	0.0159 (7)	0.0191 (8)	0.0017 (6)	−0.0019 (6)	−0.0002 (6)
O1	0.0434 (9)	0.0202 (7)	0.0328 (8)	−0.0012 (6)	0.0019 (7)	0.0100 (6)
O2	0.0252 (7)	0.0188 (6)	0.0278 (7)	0.0011 (6)	0.0083 (6)	0.0043 (6)
O3	0.0168 (6)	0.0202 (6)	0.0258 (7)	0.0017 (5)	0.0021 (5)	0.0066 (6)
O4	0.0179 (6)	0.0328 (8)	0.0388 (9)	−0.0034 (6)	0.0008 (6)	0.0191 (7)
C1	0.0548 (16)	0.0247 (11)	0.0412 (14)	−0.0029 (11)	−0.0002 (11)	0.0160 (10)
C2	0.0350 (11)	0.0190 (9)	0.0193 (9)	−0.0079 (8)	−0.0060 (8)	0.0005 (8)
C3	0.0362 (11)	0.0273 (10)	0.0217 (10)	−0.0148 (9)	−0.0026 (8)	0.0045 (8)
C4	0.0291 (11)	0.0356 (11)	0.0230 (10)	−0.0119 (9)	0.0008 (8)	0.0000 (9)
C5	0.0261 (10)	0.0278 (10)	0.0235 (10)	−0.0024 (8)	0.0026 (8)	0.0014 (8)
C6	0.0275 (10)	0.0203 (9)	0.0147 (8)	−0.0035 (7)	0.0006 (7)	−0.0008 (7)
C7	0.0296 (10)	0.0168 (9)	0.0151 (9)	−0.0037 (7)	−0.0018 (7)	0.0002 (7)
C8	0.0306 (10)	0.0152 (9)	0.0173 (9)	0.0007 (7)	−0.0023 (7)	−0.0020 (7)
C9	0.0247 (9)	0.0191 (8)	0.0224 (11)	0.0057 (7)	0.0033 (7)	0.0010 (7)
C10	0.0216 (9)	0.0236 (9)	0.0230 (10)	0.0053 (8)	−0.0035 (8)	0.0038 (8)
C11	0.0149 (9)	0.0222 (9)	0.0250 (11)	0.0016 (7)	−0.0033 (7)	0.0028 (7)
C12	0.0160 (8)	0.0181 (8)	0.0203 (9)	−0.0007 (7)	0.0001 (6)	−0.0002 (7)
C13	0.0177 (8)	0.0160 (8)	0.0196 (9)	0.0005 (7)	−0.0016 (7)	0.0023 (7)
C14	0.0174 (8)	0.0202 (9)	0.0236 (9)	−0.0020 (7)	−0.0003 (7)	0.0031 (7)
C15	0.0244 (9)	0.0183 (9)	0.0252 (9)	0.0015 (7)	−0.0011 (8)	0.0062 (8)
C16	0.0215 (9)	0.0206 (10)	0.0301 (10)	0.0053 (7)	−0.0043 (8)	0.0038 (8)
C17	0.0162 (9)	0.0221 (9)	0.0295 (10)	0.0018 (7)	0.0019 (7)	0.0029 (8)
C18	0.0193 (9)	0.0160 (8)	0.0198 (9)	0.0005 (7)	0.0017 (7)	−0.0013 (7)
C19	0.0267 (10)	0.0298 (11)	0.0321 (11)	−0.0056 (8)	0.0026 (8)	0.0125 (9)

Geometric parameters (Å, º) top

Cu—N1	1.9554 (15)	C6—C7	1.425 (3)
Cu—N2	1.9602 (15)	C7—C8	1.434 (3)
Cu—O2	1.9136 (14)	C8—H8A	0.950
Cu—O3	1.8996 (13)	C9—H9A	0.990
N1—C8	1.291 (2)	C9—H9B	0.990
N1—C9	1.471 (2)	C9—C10	1.527 (3)
N2—C11	1.491 (2)	C10—H10A	0.990
N2—C12	1.296 (2)	C10—H10B	0.990
O1—C1	1.436 (3)	C10—C11	1.519 (3)
O1—C2	1.364 (3)	C11—H11A	0.990
O2—C6	1.296 (2)	C11—H11B	0.990
O3—C18	1.299 (2)	C12—H12A	0.950
O4—C14	1.369 (2)	C12—C13	1.435 (3)
O4—C19	1.427 (2)	C13—C14	1.426 (2)
C1—H1A	0.980	C13—C18	1.424 (3)
C1—H1B	0.980	C14—C15	1.380 (3)
C1—H1C	0.980	C15—H15A	0.950
C2—C3	1.381 (3)	C15—C16	1.410 (3)
C2—C7	1.433 (3)	C16—H16A	0.950
C3—H3A	0.950	C16—C17	1.366 (3)
C3—C4	1.395 (3)	C17—H17A	0.950
C4—H4A	0.950	C17—C18	1.415 (3)
C4—C5	1.373 (3)	C19—H19A	0.980
C5—H5A	0.950	C19—H19B	0.980
C5—C6	1.419 (3)	C19—H19C	0.980

N1—Cu—N2	96.88 (6)	N1—C9—H9B	109.7
N1—Cu—O2	91.31 (6)	N1—C9—C10	109.62 (15)
N1—Cu—O3	159.21 (6)	H9A—C9—H9B	108.2
N2—Cu—O2	163.48 (6)	H9A—C9—C10	109.7
N2—Cu—O3	92.48 (6)	H9B—C9—C10	109.7
O2—Cu—O3	84.63 (6)	C9—C10—H10A	109.1
Cu—N1—C8	125.50 (14)	C9—C10—H10B	109.1
Cu—N1—C9	117.51 (11)	C9—C10—C11	112.44 (17)
C8—N1—C9	116.98 (16)	H10A—C10—H10B	107.8
Cu—N2—C11	123.81 (12)	H10A—C10—C11	109.1
Cu—N2—C12	123.91 (13)	H10B—C10—C11	109.1
C11—N2—C12	112.28 (15)	N2—C11—C10	113.84 (16)
C1—O1—C2	117.18 (19)	N2—C11—H11A	108.8
Cu—O2—C6	130.69 (13)	N2—C11—H11B	108.8
Cu—O3—C18	130.41 (12)	C10—C11—H11A	108.8
C14—O4—C19	118.35 (15)	C10—C11—H11B	108.8
O1—C1—H1A	109.5	H11A—C11—H11B	107.7
O1—C1—H1B	109.5	N2—C12—H12A	116.0
O1—C1—H1C	109.5	N2—C12—C13	128.01 (18)
H1A—C1—H1B	109.5	H12A—C12—C13	116.0
H1A—C1—H1C	109.5	C12—C13—C14	119.04 (16)
H1B—C1—H1C	109.5	C12—C13—C18	121.84 (17)
O1—C2—C3	123.98 (18)	C14—C13—C18	118.96 (16)
O1—C2—C7	114.55 (19)	O4—C14—C13	114.90 (16)
C3—C2—C7	121.5 (2)	O4—C14—C15	123.54 (17)
C2—C3—H3A	120.9	C13—C14—C15	121.56 (17)
C2—C3—C4	118.23 (19)	C14—C15—H15A	120.8
H3A—C3—C4	120.9	C14—C15—C16	118.30 (18)
C3—C4—H4A	118.6	H15A—C15—C16	120.8
C3—C4—C5	122.8 (2)	C15—C16—H16A	119.1
H4A—C4—C5	118.6	C15—C16—C17	121.85 (17)
C4—C5—H5A	119.9	H16A—C16—C17	119.1
C4—C5—C6	120.22 (19)	C16—C17—H17A	119.5
H5A—C5—C6	119.9	C16—C17—C18	121.01 (17)
O2—C6—C5	119.12 (18)	H17A—C17—C18	119.5
O2—C6—C7	122.45 (17)	O3—C18—C13	122.87 (16)
C5—C6—C7	118.42 (18)	O3—C18—C17	118.81 (16)
C2—C7—C6	118.89 (18)	C13—C18—C17	118.31 (17)
C2—C7—C8	118.50 (18)	O4—C19—H19A	109.5
C6—C7—C8	122.19 (17)	O4—C19—H19B	109.5
N1—C8—C7	126.84 (18)	O4—C19—H19C	109.5
N1—C8—H8A	116.6	H19A—C19—H19B	109.5
C7—C8—H8A	116.6	H19A—C19—H19C	109.5
N1—C9—H9A	109.7	H19B—C19—H19C	109.5

N2—Cu—N1—C8	174.63 (16)	C3—C2—C7—C6	−1.4 (3)
N2—Cu—N1—C9	−3.89 (14)	C3—C2—C7—C8	171.33 (19)
O2—Cu—N1—C8	9.01 (16)	Cu—N1—C8—C7	−4.0 (3)
O2—Cu—N1—C9	−169.52 (13)	C9—N1—C8—C7	174.53 (18)
O3—Cu—N1—C8	−69.2 (3)	C2—C7—C8—N1	−178.13 (18)
O3—Cu—N1—C9	112.24 (19)	C6—C7—C8—N1	−5.7 (3)
N1—Cu—N2—C11	−25.55 (15)	Cu—N1—C9—C10	51.28 (18)
N1—Cu—N2—C12	154.49 (15)	C8—N1—C9—C10	−127.38 (18)
O2—Cu—N2—C11	93.6 (3)	N1—C9—C10—C11	−81.9 (2)
O2—Cu—N2—C12	−86.3 (3)	Cu—N2—C11—C10	5.3 (2)
O3—Cu—N2—C11	173.05 (14)	C12—N2—C11—C10	−174.79 (16)
O3—Cu—N2—C12	−6.91 (15)	C9—C10—C11—N2	49.3 (2)
N1—Cu—O2—C6	−8.50 (17)	Cu—N2—C12—C13	5.1 (3)
N2—Cu—O2—C6	−128.4 (2)	C11—N2—C12—C13	−174.83 (18)
O3—Cu—O2—C6	151.08 (17)	N2—C12—C13—C14	176.99 (18)
N1—Cu—O3—C18	−112.2 (2)	N2—C12—C13—C18	1.7 (3)
N2—Cu—O3—C18	4.62 (16)	C19—O4—C14—C13	−176.82 (17)
O2—Cu—O3—C18	168.31 (16)	C19—O4—C14—C15	3.2 (3)
C1—O1—C2—C3	−8.9 (3)	C12—C13—C14—O4	4.0 (3)
C1—O1—C2—C7	169.63 (19)	C12—C13—C14—C15	−176.04 (18)
O1—C2—C3—C4	179.44 (19)	C18—C13—C14—O4	179.49 (17)
C7—C2—C3—C4	1.0 (3)	C18—C13—C14—C15	−0.6 (3)
C2—C3—C4—C5	0.4 (3)	O4—C14—C15—C16	−179.7 (2)
C3—C4—C5—C6	−1.3 (3)	C13—C14—C15—C16	0.3 (3)
Cu—O2—C6—C5	−179.00 (14)	C14—C15—C16—C17	−0.1 (3)
Cu—O2—C6—C7	2.3 (3)	C15—C16—C17—C18	0.0 (3)
C4—C5—C6—O2	−177.84 (19)	Cu—O3—C18—C13	0.2 (3)
C4—C5—C6—C7	0.9 (3)	Cu—O3—C18—C17	179.72 (13)
O2—C6—C7—C2	179.10 (17)	C16—C17—C18—O3	−179.84 (18)
O2—C6—C7—C8	6.7 (3)	C16—C17—C18—C13	−0.3 (3)
C5—C6—C7—C2	0.4 (3)	C12—C13—C18—O3	−4.6 (3)
C5—C6—C7—C8	−172.05 (18)	C12—C13—C18—C17	175.85 (18)
O1—C2—C7—C6	−179.93 (17)	C14—C13—C18—O3	−179.93 (17)
O1—C2—C7—C8	−7.2 (3)	C14—C13—C18—C17	0.5 (3)

Experimental details

Crystal data
Chemical formula	[Cu(C₁₉H₂₀N₂O₄)]
M_r	403.91
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	150
a, b, c (Å)	13.7911 (14), 12.7032 (13), 9.9329 (10)
V (Å³)	1740.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART 1K CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2005a)
T_min, T_max	0.700, 0.785
No. of measured, independent and observed [I > 2σ(I)] reflections	14731, 4157, 3766
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.063, 1.04
No. of reflections	4157
No. of parameters	237
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.44
Absolute structure	Flack (1983), 1916 Friedel pairs
Absolute structure parameter	0.013 (12)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2005b), DIAMOND (Brandenburg, 2007), SHELXTL and local programs.

Selected geometric parameters (Å, º) top

Cu—N1	1.9554 (15)	Cu—O2	1.9136 (14)
Cu—N2	1.9602 (15)	Cu—O3	1.8996 (13)

N1—Cu—N2	96.88 (6)	N2—Cu—O2	163.48 (6)
N1—Cu—O2	91.31 (6)	N2—Cu—O3	92.48 (6)
N1—Cu—O3	159.21 (6)	O2—Cu—O3	84.63 (6)

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[N,N'-Bis(6-methoxy­salicyl­idene)-1,3-di­amino­propane]copper(II)