[N,N′-Bis(2-oxido­naphthyl­methyl­idene)­ethane-1,2-di­amine-κ⁴O,N,N′,O′]copper(II)

The title complex, [Cu(C₂₄H₁₈N₂O₂)], has been synthesized and characterized. It is a mononuclear copper(II) complex. The Cu atom is four-coordinated by two N atoms and two O atoms of the bis-Schiff base ligand in a slightly distorted square-planar geometry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.067
• wR factor = 0.155
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT410_ALERT_2_C Short Intra H...H Contact  H8     ..  H11     ..       1.98 Ang.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

[N,N'-Bis(2-oxidonaphthylmethylidene)ethane-1,2-diamine- κ⁴O,N,N',O']copper(II)

Crystal data

[Cu(C24H18N2O2)]	F(000) = 884
Mr = 429.94	Dx = 1.558 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.644 (4) Å	Cell parameters from 2872 reflections
b = 8.165 (2) Å	θ = 2.7–25.2°
c = 12.922 (3) Å	µ = 1.22 mm^−1
β = 99.99 (3)°	T = 293 K
V = 1833.4 (7) Å^3	Block, blue
Z = 4	0.32 × 0.18 × 0.10 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3743 independent reflections
Radiation source: fine-focus sealed tube	3007 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.697, Tmax = 0.888	k = −10→4
8092 measured reflections	l = −15→16

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0679P)^2] where P = (Fo^2 + 2Fc^2)/3
3743 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.66 e Å^−3
0 restraints	Δρmin = −0.43 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.

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
Cu1	0.47705 (3)	0.16521 (7)	0.42705 (4)	0.0321 (2)
O1	0.40298 (15)	0.0795 (4)	0.3231 (2)	0.0335 (7)
O2	0.54855 (15)	0.0665 (4)	0.3587 (2)	0.0328 (7)
N1	0.4064 (2)	0.2687 (4)	0.4935 (2)	0.0317 (8)
N2	0.55048 (19)	0.2402 (4)	0.5342 (2)	0.0297 (8)
C1	0.2898 (2)	0.1832 (5)	0.3788 (3)	0.0324 (10)
C2	0.3287 (2)	0.0885 (5)	0.3142 (3)	0.0332 (10)
C3	0.2847 (3)	−0.0028 (6)	0.2298 (3)	0.0403 (11)
H3	0.3111	−0.0726	0.1879	0.080*
C4	0.2072 (3)	0.0064 (6)	0.2104 (4)	0.0452 (12)
H4	0.1790	−0.0548	0.1528	0.080*
C5	0.0842 (3)	0.1174 (7)	0.2471 (5)	0.0598 (15)
H5	0.0571	0.0568	0.1885	0.080*
C6	0.0453 (3)	0.2118 (8)	0.3053 (5)	0.0679 (17)
H6	−0.0097	0.2210	0.2876	0.080*
C7	0.0844 (3)	0.2939 (7)	0.3915 (5)	0.0633 (16)
H7	0.0563	0.3603	0.4331	0.080*
C8	0.1629 (3)	0.2849 (7)	0.4180 (4)	0.0508 (13)
H8	0.1892	0.3424	0.4786	0.080*
C9	0.1660 (3)	0.1046 (6)	0.2712 (4)	0.0436 (12)
C10	0.2056 (3)	0.1918 (6)	0.3575 (3)	0.0380 (11)
C11	0.3320 (2)	0.2667 (5)	0.4666 (3)	0.0357 (10)
H11	0.3030	0.3265	0.5105	0.080*
C12	0.4403 (2)	0.3655 (6)	0.5860 (3)	0.0384 (11)
H12A	0.4081	0.3608	0.6386	0.080*
H12B	0.4454	0.4778	0.5662	0.080*
C13	0.5189 (2)	0.2955 (6)	0.6267 (3)	0.0376 (11)
H13A	0.5521	0.3758	0.6654	0.080*
H13B	0.5141	0.2046	0.6723	0.080*
C14	0.6242 (2)	0.2358 (5)	0.5407 (3)	0.0333 (10)
H14	0.6547	0.2836	0.6020	0.080*
C15	0.6639 (2)	0.1673 (5)	0.4650 (3)	0.0313 (9)
C16	0.6231 (2)	0.0772 (5)	0.3806 (3)	0.0320 (10)
C17	0.6648 (3)	−0.0127 (5)	0.3144 (3)	0.0397 (11)
H17	0.6367	−0.0752	0.2574	0.080*
C18	0.7425 (3)	−0.0113 (6)	0.3301 (4)	0.0455 (12)
H18	0.7691	−0.0747	0.2850	0.080*
C19	0.8677 (3)	0.0827 (7)	0.4291 (5)	0.0581 (14)
H19	0.8938	0.0193	0.3835	0.080*
C20	0.9083 (3)	0.1705 (8)	0.5077 (5)	0.0697 (18)
H20	0.9635	0.1693	0.5183	0.080*
C21	0.8713 (3)	0.2625 (8)	0.5726 (5)	0.0607 (15)
H21	0.9013	0.3249	0.6281	0.080*
C22	0.7925 (3)	0.2665 (7)	0.5596 (4)	0.0498 (13)
H22	0.7675	0.3326	0.6051	0.080*
C23	0.7474 (2)	0.1728 (6)	0.4796 (3)	0.0376 (10)
C24	0.7859 (3)	0.0819 (6)	0.4126 (4)	0.0435 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0333 (3)	0.0369 (3)	0.0261 (3)	0.0005 (2)	0.0049 (2)	0.0000 (2)
O1	0.0303 (16)	0.0445 (18)	0.0259 (14)	−0.0014 (14)	0.0057 (12)	−0.0058 (13)
O2	0.0307 (15)	0.0394 (17)	0.0281 (14)	−0.0012 (13)	0.0041 (12)	−0.0038 (13)
N1	0.038 (2)	0.032 (2)	0.0260 (17)	0.0012 (16)	0.0093 (16)	0.0018 (15)
N2	0.0339 (19)	0.032 (2)	0.0229 (16)	−0.0028 (16)	0.0046 (15)	−0.0013 (15)
C1	0.030 (2)	0.035 (2)	0.032 (2)	0.0025 (19)	0.0042 (18)	0.0063 (19)
C2	0.034 (2)	0.035 (2)	0.030 (2)	0.000 (2)	0.0033 (19)	0.0076 (19)
C3	0.046 (3)	0.040 (3)	0.035 (2)	−0.006 (2)	0.007 (2)	−0.002 (2)
C4	0.041 (3)	0.049 (3)	0.042 (3)	−0.010 (2)	−0.001 (2)	0.001 (2)
C5	0.039 (3)	0.067 (4)	0.069 (4)	−0.006 (3)	−0.004 (3)	0.000 (3)
C6	0.028 (3)	0.078 (4)	0.096 (5)	0.002 (3)	0.006 (3)	0.002 (4)
C7	0.036 (3)	0.072 (4)	0.084 (4)	0.013 (3)	0.016 (3)	0.002 (3)
C8	0.035 (3)	0.057 (3)	0.062 (3)	0.002 (2)	0.011 (2)	0.003 (3)
C9	0.033 (2)	0.048 (3)	0.048 (3)	−0.005 (2)	0.003 (2)	0.007 (2)
C10	0.037 (2)	0.038 (3)	0.039 (2)	0.002 (2)	0.007 (2)	0.011 (2)
C11	0.035 (2)	0.041 (3)	0.033 (2)	0.008 (2)	0.010 (2)	0.007 (2)
C12	0.041 (3)	0.043 (3)	0.031 (2)	0.003 (2)	0.008 (2)	−0.007 (2)
C13	0.044 (3)	0.042 (3)	0.026 (2)	−0.003 (2)	0.0063 (19)	−0.011 (2)
C14	0.036 (2)	0.031 (2)	0.031 (2)	−0.0038 (19)	0.0006 (19)	0.0049 (19)
C15	0.034 (2)	0.030 (2)	0.030 (2)	−0.0006 (19)	0.0048 (18)	0.0054 (19)
C16	0.031 (2)	0.034 (2)	0.033 (2)	0.006 (2)	0.0089 (18)	0.0105 (19)
C17	0.043 (3)	0.039 (3)	0.037 (2)	0.006 (2)	0.008 (2)	−0.001 (2)
C18	0.042 (3)	0.045 (3)	0.052 (3)	0.008 (2)	0.013 (2)	0.000 (2)
C19	0.036 (3)	0.067 (4)	0.073 (4)	0.009 (3)	0.014 (3)	0.014 (3)
C20	0.032 (3)	0.080 (5)	0.093 (5)	−0.009 (3)	0.000 (3)	0.017 (4)
C21	0.041 (3)	0.071 (4)	0.066 (4)	−0.009 (3)	−0.002 (3)	0.003 (3)
C22	0.041 (3)	0.054 (3)	0.052 (3)	−0.003 (2)	0.000 (2)	0.007 (3)
C23	0.035 (2)	0.038 (3)	0.038 (2)	−0.002 (2)	0.001 (2)	0.007 (2)
C24	0.037 (3)	0.043 (3)	0.052 (3)	0.002 (2)	0.012 (2)	0.010 (2)

Geometric parameters (Å, º)

Cu1—N2	1.830 (3)	C9—C10	1.404 (6)
Cu1—N1	1.837 (3)	C11—H11	0.960
Cu1—O1	1.842 (3)	C12—C13	1.508 (6)
Cu1—O2	1.846 (3)	C12—H12A	0.960
O1—C2	1.298 (5)	C12—H12B	0.960
O2—C16	1.299 (4)	C13—H13A	0.960
N1—C11	1.299 (5)	C13—H13B	0.960
N1—C12	1.470 (5)	C14—C15	1.413 (6)
N2—C14	1.290 (5)	C14—H14	0.960
N2—C13	1.474 (5)	C15—C16	1.406 (6)
C1—C2	1.402 (6)	C15—C23	1.453 (6)
C1—C11	1.419 (6)	C16—C17	1.425 (6)
C1—C10	1.464 (6)	C17—C18	1.351 (6)
C2—C3	1.434 (6)	C17—H17	0.960
C3—C4	1.349 (6)	C18—C24	1.421 (6)
C3—H3	0.960	C18—H18	0.960
C4—C9	1.409 (7)	C19—C20	1.343 (8)
C4—H4	0.960	C19—C24	1.422 (6)
C5—C6	1.345 (8)	C19—H19	0.960
C5—C9	1.426 (6)	C20—C21	1.373 (8)
C5—H5	0.960	C20—H20	0.960
C6—C7	1.379 (8)	C21—C22	1.371 (6)
C6—H6	0.960	C21—H21	0.960
C7—C8	1.369 (6)	C22—C23	1.415 (6)
C7—H7	0.960	C22—H22	0.960
C8—C10	1.401 (6)	C23—C24	1.402 (6)
C8—H8	0.960
N2—Cu1—N1	86.61 (15)	C1—C11—H11	117.2
N2—Cu1—O1	176.97 (14)	N1—C12—C13	107.4 (3)
N1—Cu1—O1	93.60 (14)	N1—C12—H12A	110.3
N2—Cu1—O2	93.18 (14)	C13—C12—H12A	111.1
N1—Cu1—O2	178.47 (14)	N1—C12—H12B	109.9
O1—Cu1—O2	86.69 (12)	C13—C12—H12B	109.4
C2—O1—Cu1	128.3 (3)	H12A—C12—H12B	108.7
C16—O2—Cu1	128.0 (3)	N2—C13—C12	106.7 (3)
C11—N1—C12	118.2 (4)	N2—C13—H13A	110.5
C11—N1—Cu1	127.3 (3)	C12—C13—H13A	111.3
C12—N1—Cu1	114.5 (3)	N2—C13—H13B	110.3
C14—N2—C13	118.3 (3)	C12—C13—H13B	109.4
C14—N2—Cu1	127.8 (3)	H13A—C13—H13B	108.7
C13—N2—Cu1	113.5 (3)	N2—C14—C15	125.6 (4)
C2—C1—C11	119.8 (4)	N2—C14—H14	117.2
C2—C1—C10	120.0 (4)	C15—C14—H14	117.2
C11—C1—C10	120.1 (4)	C16—C15—C14	119.7 (4)
O1—C2—C1	124.8 (4)	C16—C15—C23	119.2 (4)
O1—C2—C3	116.3 (4)	C14—C15—C23	120.7 (4)
C1—C2—C3	118.9 (4)	O2—C16—C15	124.6 (4)
C4—C3—C2	120.7 (4)	O2—C16—C17	116.3 (4)
C4—C3—H3	120.3	C15—C16—C17	119.1 (4)
C2—C3—H3	119.0	C18—C17—C16	121.4 (4)
C3—C4—C9	122.2 (4)	C18—C17—H17	119.6
C3—C4—H4	119.1	C16—C17—H17	119.0
C9—C4—H4	118.7	C17—C18—C24	121.2 (4)
C6—C5—C9	121.1 (5)	C17—C18—H18	119.6
C6—C5—H5	120.2	C24—C18—H18	119.2
C9—C5—H5	118.7	C20—C19—C24	120.6 (5)
C5—C6—C7	119.8 (5)	C20—C19—H19	120.1
C5—C6—H6	120.3	C24—C19—H19	119.2
C7—C6—H6	119.9	C19—C20—C21	120.4 (5)
C8—C7—C6	121.3 (5)	C19—C20—H20	119.8
C8—C7—H7	119.2	C21—C20—H20	119.8
C6—C7—H7	119.5	C22—C21—C20	121.2 (5)
C7—C8—C10	120.5 (5)	C22—C21—H21	119.6
C7—C8—H8	120.2	C20—C21—H21	119.2
C10—C8—H8	119.3	C21—C22—C23	120.4 (5)
C10—C9—C4	119.8 (4)	C21—C22—H22	120.2
C10—C9—C5	118.8 (5)	C23—C22—H22	119.4
C4—C9—C5	121.3 (5)	C24—C23—C22	117.8 (4)
C8—C10—C9	118.4 (4)	C24—C23—C15	119.5 (4)
C8—C10—C1	123.2 (4)	C22—C23—C15	122.7 (4)
C9—C10—C1	118.3 (4)	C23—C24—C18	119.4 (4)
N1—C11—C1	125.9 (4)	C23—C24—C19	119.5 (5)
N1—C11—H11	117.0	C18—C24—C19	121.1 (5)
N1—Cu1—O1—C2	−4.4 (4)	Cu1—N1—C11—C1	−0.3 (6)
O2—Cu1—O1—C2	177.1 (4)	C2—C1—C11—N1	2.0 (7)
N2—Cu1—O2—C16	−8.1 (3)	C10—C1—C11—N1	−179.8 (4)
O1—Cu1—O2—C16	174.9 (3)	C11—N1—C12—C13	156.8 (4)
N2—Cu1—N1—C11	−176.0 (4)	Cu1—N1—C12—C13	−24.1 (4)
O1—Cu1—N1—C11	1.0 (4)	C14—N2—C13—C12	153.3 (4)
N2—Cu1—N1—C12	5.1 (3)	Cu1—N2—C13—C12	−32.7 (4)
O1—Cu1—N1—C12	−177.9 (3)	N1—C12—C13—N2	34.6 (5)
N1—Cu1—N2—C14	−170.4 (4)	C13—N2—C14—C15	171.6 (4)
O2—Cu1—N2—C14	8.1 (4)	Cu1—N2—C14—C15	−1.4 (6)
N1—Cu1—N2—C13	16.4 (3)	N2—C14—C15—C16	−8.5 (6)
O2—Cu1—N2—C13	−165.1 (3)	N2—C14—C15—C23	178.6 (4)
Cu1—O1—C2—C1	7.3 (6)	Cu1—O2—C16—C15	1.3 (6)
Cu1—O1—C2—C3	−174.5 (3)	Cu1—O2—C16—C17	180.0 (3)
C11—C1—C2—O1	−5.6 (6)	C14—C15—C16—O2	8.5 (6)
C10—C1—C2—O1	176.2 (4)	C23—C15—C16—O2	−178.5 (4)
C11—C1—C2—C3	176.2 (4)	C14—C15—C16—C17	−170.2 (4)
C10—C1—C2—C3	−1.9 (6)	C23—C15—C16—C17	2.8 (6)
O1—C2—C3—C4	−176.1 (4)	O2—C16—C17—C18	−179.7 (4)
C1—C2—C3—C4	2.3 (6)	C15—C16—C17—C18	−0.9 (6)
C2—C3—C4—C9	−0.1 (7)	C16—C17—C18—C24	−0.9 (7)
C9—C5—C6—C7	−1.9 (9)	C24—C19—C20—C21	−0.8 (9)
C5—C6—C7—C8	1.6 (9)	C19—C20—C21—C22	0.5 (9)
C6—C7—C8—C10	0.3 (9)	C20—C21—C22—C23	1.1 (8)
C3—C4—C9—C10	−2.5 (7)	C21—C22—C23—C24	−2.4 (7)
C3—C4—C9—C5	177.7 (5)	C21—C22—C23—C15	177.5 (5)
C6—C5—C9—C10	0.4 (8)	C16—C15—C23—C24	−3.0 (6)
C6—C5—C9—C4	−179.8 (5)	C14—C15—C23—C24	169.9 (4)
C7—C8—C10—C9	−1.9 (7)	C16—C15—C23—C22	177.1 (4)
C7—C8—C10—C1	177.1 (5)	C14—C15—C23—C22	−10.0 (6)
C4—C9—C10—C8	−178.3 (4)	C22—C23—C24—C18	−178.8 (4)
C5—C9—C10—C8	1.5 (7)	C15—C23—C24—C18	1.3 (7)
C4—C9—C10—C1	2.7 (7)	C22—C23—C24—C19	2.1 (7)
C5—C9—C10—C1	−177.5 (4)	C15—C23—C24—C19	−177.8 (4)
C2—C1—C10—C8	−179.4 (4)	C17—C18—C24—C23	0.7 (7)
C11—C1—C10—C8	2.4 (6)	C17—C18—C24—C19	179.8 (5)
C2—C1—C10—C9	−0.5 (6)	C20—C19—C24—C23	−0.5 (8)
C11—C1—C10—C9	−178.7 (4)	C20—C19—C24—C18	−179.6 (5)
C12—N1—C11—C1	178.6 (4)