[1,1'-Diphenyl-3,3'-(propane-1,3-diyldinitrilo)dibut-1-enolato]copper(II).

The title compound, [Cu(C(23)H(24)N(2)O(2))] or [Cu{(BA)(2)pn}], where (BA)(2)pn is 1,1'-diphenyl-3,3'-(propane-1,3-diyldinitrilo)dibut-1-enolate, is a mononuclear copper(II) complex, located on a twofold axis. The four-coordinate Cu(II) atom is in a tetra-hedrally distorted square plane defined by the N and O atoms of the Schiff base ligand. In the tetra-dentate ligand, the two chelate rings are twisted relative to each other, making a dihedral angle of 36.57 (3)°.

Related literature

For general background, see: Bunce et al. (1998 ▶); Klement et al. (1999 ▶); Meghdadi et al. (2008 ▶); Mikuriya et al. (2002 ▶); Filomeni et al. (2007 ▶). For a structure determination of the title compound in space group Cc, see: Sarkar et al. (2008 ▶). For the structure of a polymorph, see: Arıcı (2006 ▶). For related structures, see: Arıcı et al. (2001 ▶); Dehghanpour et al. (2005 ▶).

Experimental

Crystal data

[Cu(C23H24N2O2)]

M = 423.98

Monoclinic,

a = 12.2047 (12) Å

b = 20.320 (2) Å

c = 8.9992 (9) Å

β = 117.405 (1)°

V = 1981.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.12 mm−1

T = 100 (2) K

0.50 × 0.46 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.57, T max = 0.68

11028 measured reflections

2881 independent reflections

2780 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.063

S = 1.05

2881 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAIn class="Chemical">NT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001081/dn2424sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001081/dn2424Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C23H24N2O2)]	F(000) = 884
Mr = 423.98	Dx = 1.421 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8926 reflections
a = 12.2047 (12) Å	θ = 2.1–30.0°
b = 20.320 (2) Å	µ = 1.12 mm−1
c = 8.9992 (9) Å	T = 100 K
β = 117.405 (1)°	Oval, black
V = 1981.3 (3) Å3	0.50 × 0.46 × 0.35 mm
Z = 4

Bruker APEXII CCD diffractometer	2881 independent reflections
Radiation source: fine-focus sealed tube	2780 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
Tmin = 0.57, Tmax = 0.68	k = −28→28
11028 measured reflections	l = −12→12

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0348P)2 + 1.3062P] where P = (Fo2 + 2Fc2)/3
2881 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. Dark crystals from methanol. Bruker Kappa APEXII CCD diffractometer, full sphere data collection.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.285854 (8)	0.2500	0.01604 (6)
O1	0.58573 (7)	0.35237 (3)	0.19375 (9)	0.01910 (14)
N1	0.62650 (9)	0.21952 (4)	0.30042 (11)	0.01918 (16)
C1	0.62862 (9)	0.44403 (5)	−0.00488 (13)	0.02073 (18)
H1A	0.5465	0.4414	−0.0198	0.025*
C2	0.66276 (10)	0.49606 (5)	−0.07553 (14)	0.0239 (2)
H2A	0.6036	0.5284	−0.1396	0.029*
C3	0.78315 (10)	0.50085 (5)	−0.05262 (13)	0.0227 (2)
H3A	0.8060	0.5360	−0.1023	0.027*
C4	0.87007 (10)	0.45401 (5)	0.04322 (13)	0.02263 (19)
H4A	0.9529	0.4578	0.0615	0.027*
C5	0.83576 (9)	0.40168 (5)	0.11223 (13)	0.02040 (18)
H5A	0.8954	0.3696	0.1767	0.024*
C6	0.71452 (9)	0.39567 (5)	0.08789 (12)	0.01713 (17)
C7	0.67614 (9)	0.33962 (5)	0.16071 (11)	0.01684 (17)
C8	0.73853 (9)	0.28017 (5)	0.18784 (13)	0.01919 (18)
H8A	0.8005	0.2772	0.1522	0.023*
C9	0.71826 (10)	0.22321 (5)	0.26408 (12)	0.01902 (18)
C10	0.81019 (10)	0.16754 (5)	0.30347 (14)	0.0251 (2)
H10A	0.7658	0.1263	0.2580	0.038*
H10B	0.8598	0.1635	0.4250	0.038*
H10C	0.8645	0.1768	0.2528	0.038*
C11	0.60558 (11)	0.16066 (5)	0.37870 (13)	0.02317 (19)
H11A	0.5853	0.1741	0.4689	0.028*
H11B	0.6821	0.1341	0.4297	0.028*
C12	0.5000	0.11873 (7)	0.2500	0.0241 (3)
H12A	0.4673	0.0900	0.3093	0.029*	0.50
H12B	0.5327	0.0900	0.1907	0.029*	0.50

	U11	U22	U33	U12	U13	U23
Cu1	0.01768 (9)	0.01421 (9)	0.01729 (9)	0.000	0.00895 (7)	0.000
O1	0.0193 (3)	0.0171 (3)	0.0243 (3)	0.0005 (2)	0.0130 (3)	0.0002 (2)
N1	0.0227 (4)	0.0162 (4)	0.0171 (4)	0.0019 (3)	0.0078 (3)	0.0007 (3)
C1	0.0175 (4)	0.0200 (4)	0.0242 (5)	−0.0008 (3)	0.0093 (4)	−0.0006 (3)
C2	0.0222 (5)	0.0208 (4)	0.0254 (5)	−0.0008 (4)	0.0083 (4)	0.0019 (4)
C3	0.0244 (5)	0.0227 (5)	0.0208 (4)	−0.0068 (4)	0.0103 (4)	−0.0020 (3)
C4	0.0192 (4)	0.0275 (5)	0.0225 (4)	−0.0055 (4)	0.0108 (4)	−0.0029 (4)
C5	0.0159 (4)	0.0240 (5)	0.0207 (4)	−0.0014 (3)	0.0079 (4)	−0.0008 (3)
C6	0.0164 (4)	0.0185 (4)	0.0164 (4)	−0.0019 (3)	0.0075 (3)	−0.0028 (3)
C7	0.0156 (4)	0.0184 (4)	0.0156 (4)	−0.0014 (3)	0.0064 (3)	−0.0026 (3)
C8	0.0174 (4)	0.0194 (4)	0.0205 (4)	0.0005 (3)	0.0085 (4)	−0.0031 (3)
C9	0.0193 (4)	0.0175 (4)	0.0161 (4)	0.0020 (3)	0.0046 (4)	−0.0033 (3)
C10	0.0238 (5)	0.0208 (5)	0.0260 (5)	0.0065 (4)	0.0075 (4)	−0.0027 (4)
C11	0.0308 (5)	0.0183 (4)	0.0199 (4)	0.0031 (4)	0.0113 (4)	0.0039 (3)
C12	0.0327 (8)	0.0159 (6)	0.0260 (7)	0.000	0.0154 (6)	0.000

Cu1—O1	1.9145 (7)	C5—C6	1.3978 (13)
Cu1—O1i	1.9145 (7)	C5—H5A	0.9500
Cu1—N1	1.9394 (9)	C6—C7	1.4928 (13)
Cu1—N1i	1.9395 (9)	C7—C8	1.3882 (13)
O1—C7	1.2943 (11)	C8—C9	1.4241 (14)
N1—C9	1.3054 (14)	C8—H8A	0.9500
N1—C11	1.4688 (13)	C9—C10	1.5158 (14)
C1—C2	1.3925 (14)	C10—H10A	0.9800
C1—C6	1.3986 (14)	C10—H10B	0.9800
C1—H1A	0.9500	C10—H10C	0.9800
C2—C3	1.3900 (15)	C11—C12	1.5342 (14)
C2—H2A	0.9500	C11—H11A	0.9900
C3—C4	1.3903 (16)	C11—H11B	0.9900
C3—H3A	0.9500	C12—C11i	1.5342 (14)
C4—C5	1.3896 (14)	C12—H12A	0.9900
C4—H4A	0.9500	C12—H12B	0.9900
O1—Cu1—O1i	90.19 (4)	O1—C7—C8	126.18 (9)
O1—Cu1—N1	94.56 (3)	O1—C7—C6	114.90 (8)
O1i—Cu1—N1	154.41 (4)	C8—C7—C6	118.91 (9)
O1—Cu1—N1i	154.41 (4)	C7—C8—C9	126.09 (9)
O1i—Cu1—N1i	94.56 (3)	C7—C8—H8A	117.0
N1—Cu1—N1i	91.94 (5)	C9—C8—H8A	117.0
C7—O1—Cu1	123.15 (6)	N1—C9—C8	121.79 (9)
C9—N1—C11	121.70 (9)	N1—C9—C10	121.77 (9)
C9—N1—Cu1	125.72 (7)	C8—C9—C10	116.43 (9)
C11—N1—Cu1	112.51 (7)	C9—C10—H10A	109.5
C2—C1—C6	120.42 (9)	C9—C10—H10B	109.5
C2—C1—H1A	119.8	H10A—C10—H10B	109.5
C6—C1—H1A	119.8	C9—C10—H10C	109.5
C3—C2—C1	120.23 (10)	H10A—C10—H10C	109.5
C3—C2—H2A	119.9	H10B—C10—H10C	109.5
C1—C2—H2A	119.9	N1—C11—C12	111.17 (8)
C2—C3—C4	119.78 (10)	N1—C11—H11A	109.4
C2—C3—H3A	120.1	C12—C11—H11A	109.4
C4—C3—H3A	120.1	N1—C11—H11B	109.4
C5—C4—C3	120.01 (10)	C12—C11—H11B	109.4
C5—C4—H4A	120.0	H11A—C11—H11B	108.0
C3—C4—H4A	120.0	C11—C12—C11i	112.54 (12)
C4—C5—C6	120.79 (10)	C11—C12—H12A	109.1
C4—C5—H5A	119.6	C11i—C12—H12A	109.1
C6—C5—H5A	119.6	C11—C12—H12B	109.1
C5—C6—C1	118.73 (9)	C11i—C12—H12B	109.1
C5—C6—C7	121.42 (9)	H12A—C12—H12B	107.8
C1—C6—C7	119.84 (9)
O1i—Cu1—O1—C7	171.40 (9)	Cu1—O1—C7—C8	−11.84 (13)
N1—Cu1—O1—C7	16.58 (8)	Cu1—O1—C7—C6	168.64 (6)
N1i—Cu1—O1—C7	−87.60 (11)	C5—C6—C7—O1	151.44 (9)
O1—Cu1—N1—C9	−12.71 (9)	C1—C6—C7—O1	−27.61 (13)
O1i—Cu1—N1—C9	−112.72 (10)	C5—C6—C7—C8	−28.11 (13)
N1i—Cu1—N1—C9	142.51 (10)	C1—C6—C7—C8	152.83 (9)
O1—Cu1—N1—C11	170.40 (7)	O1—C7—C8—C9	−3.07 (16)
O1i—Cu1—N1—C11	70.39 (11)	C6—C7—C8—C9	176.44 (9)
N1i—Cu1—N1—C11	−34.37 (6)	C11—N1—C9—C8	179.86 (9)
C6—C1—C2—C3	−0.83 (16)	Cu1—N1—C9—C8	3.24 (14)
C1—C2—C3—C4	−0.93 (16)	C11—N1—C9—C10	−1.20 (15)
C2—C3—C4—C5	1.64 (16)	Cu1—N1—C9—C10	−177.83 (7)
C3—C4—C5—C6	−0.59 (15)	C7—C8—C9—N1	7.75 (16)
C4—C5—C6—C1	−1.15 (15)	C7—C8—C9—C10	−171.24 (10)
C4—C5—C6—C7	179.79 (9)	C9—N1—C11—C12	−102.55 (11)
C2—C1—C6—C5	1.85 (15)	Cu1—N1—C11—C12	74.48 (9)
C2—C1—C6—C7	−179.07 (9)	N1—C11—C12—C11i	−37.68 (6)