Bis{4-bromo-2-[(naphthalen-1-yl­imino)­meth­yl]phenolato-κ2N,O}copper(II)

Shahverdizadeh, G.H.; Ng, S.W.; Tiekink, E.R.T.; Mirtamizdoust, B.

doi:10.1107/S1600536812004989

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m278

doi:10.1107/S1600536812004989

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Bis{4-bromo-2-[(naphthalen-1-ylimino)methyl]phenolato-κ²N,O}copper(II)

Gholam Hossein Shahverdizadeh,^a ‡ Seik Weng Ng,^b,^c Edward R. T. Tiekink ^b ^* and Babak Mirtamizdoust ^d

^aDepartment of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, PO Box 1655, Tabriz, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^dDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Tabriz, PO Box 5166616471, Tabriz, Iran
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 28 January 2012; accepted 4 February 2012; online 10 February 2012)

The title complex, [Cu(C₁₇H₁₁BrNO)₂], lies on a centre of inversion. The chelating Schiff base anions define a square-planar N₂O₂ donor set. The nearly perpendicular orientation of the naphthyl residues of the chelate ring [dihedral angle = 82.12 (12)°] precludes the Cu^II centre from additional coordination. In the refinement, the naphthyl rings were found to be disordered over two positions.; the major component has a site occupancy of 0.667 (4).

Related literature

For background to related Cu^II Schiff base compounds, see: Safaei et al. (2010 ). For a related structure, see: Dong et al. (2007 ). For specialized crystallization techniques, see: Harrowfield et al. (1996 ).

Experimental

Crystal data

[Cu(C₁₇H₁₁BrNO)₂]
M_r = 713.90
Monoclinic, P 2₁ /c
a = 11.4572 (6) Å
b = 9.5782 (3) Å
c = 13.8108 (6) Å
β = 114.047 (5)°
V = 1384.05 (10) Å³
Z = 2
Cu Kα radiation
μ = 4.78 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.381, T_max = 0.796
15204 measured reflections
2888 independent reflections
2670 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.157
S = 1.10
2888 reflections
240 parameters
69 restraints
H-atom parameters constrained
Δρ_max = 0.95 e Å⁻³
Δρ_min = −1.09 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812004989/pv2510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004989/pv2510Isup2.hkl

checkCIF report

Comment top

There has been recent interest in the chemistry of Schiff base Cu^II complexes related to the title complex (Safaei et al., 2010). In the title molecule (Fig. 1), the Cu^II atom is located on a crystallographic centre of inversion. The Cu^II atom is N,O-chelated by the Schiff base anions to define a square planar N₂O₂ geometry. The five-membered chelate ring is almost planar with a r.m.s. deviation = 0.173 °. The maximum deviation from the least-squares plane through the chelate ring is -0.178 (7) Å for the N1 atom. The naphthyl ring is almost perpendicular to the chelate ring forming a dihedral angle of 82.12 (12)°. This precludes the close approach of other atoms to the Cu^II centre.

The structure resembles very closely to that reported for the unsubstituted derivative (Dong et al., 2007).

The disorder in the structure precludes a detailed description of the crystal packing. However, the closest interactions are of the type C—H···π involving components of the disordered naphthyl residue. Globally, molecules assemble into layers via weak C—H···π interactions that stack along the a axis (Fig. 2).

Related literature top

For background to related Cu^II Schiff base compounds, see: Safaei et al. (2010). For a related structure, see: Dong et al. (2007). For specialized crystallization techniques, see: Harrowfield et al. (1996).

Experimental top

A solution of 1-naphthaldehyde (10 mmol) in EtOH (25 ml) was added drop-wise to a solution of 2-(aminomethyl)-4-bromophenol (10 mmol) in EtOH (15 ml). The mixture was refluxed for 9 h. The precipitate was removed by filtration and recrystallized from a MeOH solution. The ligand (0.5 mmol) was placed in one arm of a branched tube (Harrowfield et al., 1996) and copper(II) perchlorate (0.5 mmol) in the other. Methanol was then added to fill both arms, the tube sealed and the ligand-containing arm immersed in a bath at 333 K, while the other was left at ambient temperature. After eight days, crystals had deposited in the arm at ambient temperature. They were filtered off, washed with acetone and ether, and air-dried. Yield: 76%. M.pt.: 572 K

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title complex showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only the major component of the disordered residue is shown. Symmetry code for the unlabeled atoms: -x+1, -y+1, -z+1.
	Fig. 2. A view in projection down the c axis of the unit-cell contents of the title complex.

Bis{4-bromo-2-[(naphthalen-1-ylimino)methyl]phenolato- κ²N,O}copper(II) top

Crystal data top

[Cu(C₁₇H₁₁BrNO)₂]	F(000) = 710
M_r = 713.90	D_x = 1.713 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 6098 reflections
a = 11.4572 (6) Å	θ = 3.5–77.0°
b = 9.5782 (3) Å	µ = 4.78 mm⁻¹
c = 13.8108 (6) Å	T = 100 K
β = 114.047 (5)°	Plate, brown
V = 1384.05 (10) Å³	0.25 × 0.20 × 0.05 mm
Z = 2

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2888 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2670 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.045
Detector resolution: 10.4041 pixels mm^-1	θ_max = 77.2°, θ_min = 4.2°
ω scan	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→12
T_min = 0.381, T_max = 0.796	l = −16→17
15204 measured reflections

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0348P)² + 6.8305P] where P = (F_o² + 2F_c²)/3
2888 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.95 e Å⁻³
69 restraints	Δρ_min = −1.09 e Å⁻³

Crystal data top

[Cu(C₁₇H₁₁BrNO)₂]	V = 1384.05 (10) Å³
M_r = 713.90	Z = 2
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.4572 (6) Å	µ = 4.78 mm⁻¹
b = 9.5782 (3) Å	T = 100 K
c = 13.8108 (6) Å	0.25 × 0.20 × 0.05 mm
β = 114.047 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2888 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2670 reflections with I > 2σ(I)
T_min = 0.381, T_max = 0.796	R_int = 0.045
15204 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	69 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.10	Δρ_max = 0.95 e Å⁻³
2888 reflections	Δρ_min = −1.09 e Å⁻³
240 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.76797 (9)	0.77617 (9)	1.04687 (5)	0.0814 (3)
Cu	0.5000	0.5000	0.5000	0.0580 (4)
O1	0.6132 (4)	0.4554 (4)	0.6397 (3)	0.0516 (9)
N1	0.4092 (6)	0.6384 (7)	0.5544 (5)	0.0423 (15)	0.677 (4)
C1	0.2833 (4)	0.6955 (5)	0.4909 (3)	0.0474 (19)	0.677 (4)
C2	0.1801 (5)	0.6389 (5)	0.5059 (4)	0.048 (2)	0.677 (4)
H2	0.1940	0.5711	0.5596	0.057*	0.677 (4)
C3	0.0565 (4)	0.6817 (6)	0.4421 (5)	0.060 (4)	0.677 (4)
H3	−0.0141	0.6431	0.4523	0.071*	0.677 (4)
C4	0.0361 (3)	0.7810 (6)	0.3635 (4)	0.059 (3)	0.677 (4)
H4	−0.0484	0.8102	0.3199	0.071*	0.677 (4)
C5	0.1393 (3)	0.8375 (4)	0.3486 (3)	0.052 (2)	0.677 (4)
C6	0.2629 (3)	0.7947 (4)	0.4123 (3)	0.048 (2)	0.677 (4)
C7	0.3661 (4)	0.8513 (6)	0.3974 (5)	0.061 (3)	0.677 (4)
H7	0.4505	0.8220	0.4409	0.074*	0.677 (4)
C8	0.3457 (5)	0.9505 (7)	0.3187 (5)	0.105 (6)	0.677 (4)
H8	0.4162	0.9892	0.3085	0.126*	0.677 (4)
C9	0.2221 (6)	0.9933 (6)	0.2550 (5)	0.087 (4)	0.677 (4)
H9	0.2081	1.0612	0.2012	0.105*	0.677 (4)
C10	0.1189 (5)	0.9368 (6)	0.2699 (4)	0.067 (3)	0.677 (4)
H10	0.0344	0.9660	0.2263	0.080*	0.677 (4)
C11	0.4702 (8)	0.7009 (8)	0.6474 (5)	0.093 (3)
H11	0.4358	0.7870	0.6578	0.112*	0.677 (4)
H11'	0.4023	0.7389	0.6619	0.112*	0.323 (4)
C12	0.5819 (5)	0.6516 (6)	0.7332 (4)	0.0497 (13)
C13	0.6202 (6)	0.7242 (7)	0.8301 (4)	0.0550 (14)
H13	0.5769	0.8070	0.8342	0.066*
C14	0.7192 (6)	0.6753 (6)	0.9174 (4)	0.0558 (15)
C15	0.7818 (6)	0.5521 (6)	0.9132 (4)	0.0587 (16)
H15	0.8495	0.5177	0.9752	0.070*
C16	0.7455 (5)	0.4806 (6)	0.8195 (4)	0.0494 (13)
H16	0.7891	0.3972	0.8172	0.059*
C17	0.6444 (5)	0.5287 (5)	0.7260 (4)	0.0430 (11)
N1'	0.4581 (13)	0.6949 (12)	0.5452 (7)	0.037 (3)	0.323 (4)
C1'	0.3748 (7)	0.7905 (10)	0.4624 (7)	0.043 (3)	0.323 (4)
C2'	0.4313 (8)	0.8883 (12)	0.4206 (9)	0.053 (5)	0.323 (4)
H2'	0.5218	0.8950	0.4478	0.064*	0.323 (4)
C3'	0.3554 (10)	0.9763 (12)	0.3393 (10)	0.046 (5)	0.323 (4)
H3'	0.3940	1.0431	0.3108	0.056*	0.323 (4)
C4'	0.2231 (10)	0.9664 (11)	0.2996 (8)	0.069 (6)	0.323 (4)
H4'	0.1712	1.0265	0.2440	0.083*	0.323 (4)
C5'	0.1666 (7)	0.8686 (9)	0.3413 (6)	0.060 (6)	0.323 (4)
C6'	0.2424 (7)	0.7807 (7)	0.4227 (6)	0.051 (6)	0.323 (4)
C7'	0.1859 (9)	0.6829 (10)	0.4644 (9)	0.042 (4)	0.323 (4)
H7'	0.2378	0.6228	0.5200	0.050*	0.323 (4)
C8'	0.0536 (10)	0.6731 (13)	0.4248 (11)	0.082 (12)	0.323 (4)
H8'	0.0149	0.6062	0.4533	0.099*	0.323 (4)
C9'	−0.0223 (7)	0.7610 (14)	0.3434 (11)	0.063 (6)	0.323 (4)
H9'	−0.1128	0.7543	0.3163	0.075*	0.323 (4)
C10'	0.0342 (7)	0.8588 (12)	0.3017 (9)	0.067 (5)	0.323 (4)
H10'	−0.0177	0.9189	0.2461	0.080*	0.323 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1176 (7)	0.0740 (5)	0.0377 (3)	−0.0287 (5)	0.0164 (4)	−0.0103 (3)
Cu	0.0604 (7)	0.0622 (8)	0.0352 (6)	0.0314 (6)	0.0028 (5)	−0.0068 (5)
O1	0.053 (2)	0.053 (2)	0.0371 (18)	0.0147 (18)	0.0062 (16)	−0.0025 (16)
N1	0.042 (4)	0.035 (3)	0.041 (3)	0.001 (3)	0.008 (3)	−0.003 (3)
C1	0.049 (5)	0.046 (4)	0.044 (4)	0.006 (4)	0.016 (4)	−0.014 (3)
C2	0.044 (4)	0.044 (5)	0.058 (5)	−0.001 (4)	0.023 (4)	−0.003 (4)
C3	0.037 (5)	0.052 (6)	0.083 (7)	−0.003 (4)	0.017 (5)	−0.024 (6)
C4	0.048 (6)	0.047 (5)	0.070 (6)	0.003 (4)	0.011 (5)	−0.018 (5)
C5	0.042 (5)	0.045 (4)	0.050 (5)	0.014 (4)	0.001 (4)	−0.011 (4)
C6	0.039 (4)	0.053 (6)	0.043 (5)	0.018 (4)	0.007 (4)	−0.010 (4)
C7	0.045 (5)	0.074 (7)	0.070 (6)	0.021 (5)	0.028 (5)	0.020 (5)
C8	0.100 (12)	0.104 (12)	0.104 (11)	0.032 (9)	0.035 (9)	0.057 (10)
C9	0.078 (8)	0.093 (9)	0.089 (9)	0.026 (7)	0.032 (7)	0.041 (8)
C10	0.063 (6)	0.062 (6)	0.058 (5)	0.023 (5)	0.008 (5)	0.002 (5)
C11	0.099 (6)	0.098 (6)	0.050 (4)	0.062 (5)	−0.002 (4)	−0.022 (4)
C12	0.050 (3)	0.055 (3)	0.038 (3)	0.008 (3)	0.012 (2)	−0.004 (2)
C13	0.061 (4)	0.055 (3)	0.045 (3)	−0.003 (3)	0.018 (3)	−0.006 (3)
C14	0.070 (4)	0.051 (3)	0.035 (3)	−0.017 (3)	0.010 (3)	0.000 (2)
C15	0.067 (4)	0.050 (3)	0.040 (3)	−0.016 (3)	0.003 (3)	0.009 (2)
C16	0.050 (3)	0.042 (3)	0.044 (3)	−0.006 (2)	0.006 (2)	0.009 (2)
C17	0.044 (3)	0.045 (3)	0.036 (2)	0.000 (2)	0.012 (2)	0.002 (2)
N1'	0.038 (6)	0.024 (5)	0.040 (6)	0.001 (5)	0.005 (5)	−0.006 (5)
C1'	0.052 (7)	0.043 (7)	0.034 (6)	0.010 (6)	0.018 (6)	0.002 (5)
C2'	0.062 (9)	0.049 (8)	0.054 (8)	0.013 (7)	0.029 (7)	0.007 (6)
C3'	0.053 (9)	0.040 (8)	0.053 (8)	0.013 (7)	0.029 (7)	0.005 (7)
C4'	0.083 (10)	0.073 (10)	0.057 (9)	0.015 (8)	0.036 (8)	−0.008 (7)
C5'	0.063 (9)	0.067 (10)	0.051 (9)	0.013 (8)	0.023 (7)	−0.007 (7)
C6'	0.056 (9)	0.044 (9)	0.051 (9)	0.001 (7)	0.019 (8)	0.000 (7)
C7'	0.035 (7)	0.030 (7)	0.060 (8)	−0.006 (5)	0.020 (6)	−0.002 (6)
C8'	0.075 (15)	0.083 (15)	0.084 (13)	−0.007 (9)	0.029 (9)	0.011 (9)
C9'	0.053 (9)	0.055 (9)	0.072 (9)	0.002 (7)	0.017 (7)	−0.010 (7)
C10'	0.070 (9)	0.057 (8)	0.064 (8)	0.010 (7)	0.017 (7)	−0.010 (7)

Geometric parameters (Å, º) top

Br1—C14	1.905 (6)	C11—H11	0.9500
Cu—O1	1.883 (3)	C11—H11'	0.9500
Cu—O1ⁱ	1.883 (3)	C12—C17	1.402 (7)
Cu—N1	2.010 (6)	C12—C13	1.410 (7)
Cu—N1ⁱ	2.010 (6)	C13—C14	1.359 (8)
Cu—N1'	2.085 (11)	C13—H13	0.9500
Cu—N1'ⁱ	2.085 (11)	C14—C15	1.394 (9)
O1—C17	1.302 (6)	C15—C16	1.371 (8)
N1—C11	1.328 (8)	C15—H15	0.9500
N1—C1	1.455 (6)	C16—C17	1.415 (7)
C1—C2	1.3900	C16—H16	0.9500
C1—C6	1.3900	N1'—C1'	1.472 (9)
C2—C3	1.3900	C1'—C2'	1.3900
C2—H2	0.9500	C1'—C6'	1.3900
C3—C4	1.3900	C2'—C3'	1.3900
C3—H3	0.9500	C2'—H2'	0.9500
C4—C5	1.3900	C3'—C4'	1.3900
C4—H4	0.9500	C3'—H3'	0.9500
C5—C6	1.3900	C4'—C5'	1.3900
C5—C10	1.3900	C4'—H4'	0.9500
C6—C7	1.3900	C5'—C6'	1.3900
C7—C8	1.3900	C5'—C10'	1.3900
C7—H7	0.9500	C6'—C7'	1.3900
C8—C9	1.3900	C7'—C8'	1.3900
C8—H8	0.9500	C7'—H7'	0.9500
C9—C10	1.3900	C8'—C9'	1.3900
C9—H9	0.9500	C8'—H8'	0.9500
C10—H10	0.9500	C9'—C10'	1.3900
C11—N1'	1.363 (10)	C9'—H9'	0.9500
C11—C12	1.424 (8)	C10'—H10'	0.9500

O1—Cu—O1ⁱ	180.000 (1)	N1'—C11—H11'	119.2
O1—Cu—N1	90.7 (2)	C12—C11—H11'	119.2
O1ⁱ—Cu—N1	89.3 (2)	C17—C12—C13	120.7 (5)
O1—Cu—N1ⁱ	89.3 (2)	C17—C12—C11	122.1 (5)
O1ⁱ—Cu—N1ⁱ	90.7 (2)	C13—C12—C11	116.9 (5)
N1—Cu—N1ⁱ	180.000 (1)	C14—C13—C12	119.8 (6)
O1—Cu—N1'	92.5 (3)	C14—C13—H13	120.1
O1ⁱ—Cu—N1'	87.5 (3)	C12—C13—H13	120.1
N1ⁱ—Cu—N1'	156.9 (4)	C13—C14—C15	120.8 (5)
O1—Cu—N1'ⁱ	87.5 (3)	C13—C14—Br1	118.6 (5)
O1ⁱ—Cu—N1'ⁱ	92.5 (3)	C15—C14—Br1	120.6 (4)
N1—Cu—N1'ⁱ	156.9 (4)	C16—C15—C14	120.0 (5)
N1'—Cu—N1'ⁱ	180.000 (2)	C16—C15—H15	120.0
C17—O1—Cu	129.3 (3)	C14—C15—H15	120.0
C11—N1—C1	114.5 (6)	C15—C16—C17	121.3 (6)
C11—N1—Cu	120.7 (5)	C15—C16—H16	119.4
C1—N1—Cu	124.0 (4)	C17—C16—H16	119.4
C2—C1—C6	120.0	O1—C17—C12	124.0 (5)
C2—C1—N1	117.3 (4)	O1—C17—C16	118.5 (5)
C6—C1—N1	122.5 (4)	C12—C17—C16	117.4 (5)
C3—C2—C1	120.0	C11—N1'—C1'	122.6 (9)
C3—C2—H2	120.0	C11—N1'—Cu	114.1 (7)
C1—C2—H2	120.0	C1'—N1'—Cu	118.7 (7)
C2—C3—C4	120.0	C2'—C1'—C6'	120.0
C2—C3—H3	120.0	C2'—C1'—N1'	118.5 (8)
C4—C3—H3	120.0	C6'—C1'—N1'	121.4 (8)
C5—C4—C3	120.0	C3'—C2'—C1'	120.0
C5—C4—H4	120.0	C3'—C2'—H2'	120.0
C3—C4—H4	120.0	C1'—C2'—H2'	120.0
C4—C5—C6	120.0	C2'—C3'—C4'	120.0
C4—C5—C10	120.0	C2'—C3'—H3'	120.0
C6—C5—C10	120.0	C4'—C3'—H3'	120.0
C7—C6—C5	120.0	C3'—C4'—C5'	120.0
C7—C6—C1	120.0	C3'—C4'—H4'	120.0
C5—C6—C1	120.0	C5'—C4'—H4'	120.0
C6—C7—C8	120.0	C6'—C5'—C4'	120.0
C6—C7—H7	120.0	C6'—C5'—C10'	120.0
C8—C7—H7	120.0	C4'—C5'—C10'	120.0
C9—C8—C7	120.0	C7'—C6'—C5'	120.0
C9—C8—H8	120.0	C7'—C6'—C1'	120.0
C7—C8—H8	120.0	C5'—C6'—C1'	120.0
C10—C9—C8	120.0	C6'—C7'—C8'	120.0
C10—C9—H9	120.0	C6'—C7'—H7'	120.0
C8—C9—H9	120.0	C8'—C7'—H7'	120.0
C9—C10—C5	120.0	C7'—C8'—C9'	120.0
C9—C10—H10	120.0	C7'—C8'—H8'	120.0
C5—C10—H10	120.0	C9'—C8'—H8'	120.0
N1—C11—C12	126.5 (6)	C8'—C9'—C10'	120.0
N1'—C11—C12	121.7 (7)	C8'—C9'—H9'	120.0
N1—C11—H11	116.7	C10'—C9'—H9'	120.0
N1'—C11—H11	108.6	C9'—C10'—C5'	120.0
C12—C11—H11	116.7	C9'—C10'—H10'	120.0
N1—C11—H11'	102.9	C5'—C10'—H10'	120.0

N1—Cu—O1—C17	−22.5 (5)	C13—C14—C15—C16	1.6 (9)
N1ⁱ—Cu—O1—C17	157.5 (5)	Br1—C14—C15—C16	179.9 (5)
N1'—Cu—O1—C17	0.6 (6)	C14—C15—C16—C17	−0.5 (9)
N1'ⁱ—Cu—O1—C17	−179.4 (6)	Cu—O1—C17—C12	10.2 (8)
O1—Cu—N1—C11	27.1 (7)	Cu—O1—C17—C16	−171.3 (4)
O1ⁱ—Cu—N1—C11	−152.9 (7)	C13—C12—C17—O1	179.1 (6)
N1'—Cu—N1—C11	−67.6 (7)	C11—C12—C17—O1	5.6 (10)
N1'ⁱ—Cu—N1—C11	112.4 (7)	C13—C12—C17—C16	0.6 (8)
O1—Cu—N1—C1	−163.7 (6)	C11—C12—C17—C16	−172.9 (7)
O1ⁱ—Cu—N1—C1	16.3 (6)	C15—C16—C17—O1	−179.2 (5)
N1'—Cu—N1—C1	101.7 (10)	C15—C16—C17—C12	−0.6 (8)
N1'ⁱ—Cu—N1—C1	−78.3 (10)	N1—C11—N1'—C1'	95.6 (15)
C11—N1—C1—C2	−89.0 (7)	C12—C11—N1'—C1'	−154.6 (10)
Cu—N1—C1—C2	101.2 (5)	N1—C11—N1'—Cu	−60.0 (8)
C11—N1—C1—C6	96.0 (8)	C12—C11—N1'—Cu	49.8 (13)
Cu—N1—C1—C6	−73.9 (6)	O1—Cu—N1'—C11	−27.8 (9)
C6—C1—C2—C3	0.0	O1ⁱ—Cu—N1'—C11	152.2 (9)
N1—C1—C2—C3	−175.2 (5)	N1—Cu—N1'—C11	58.1 (7)
C1—C2—C3—C4	0.0	N1ⁱ—Cu—N1'—C11	−121.9 (7)
C2—C3—C4—C5	0.0	O1—Cu—N1'—C1'	175.5 (9)
C3—C4—C5—C6	0.0	O1ⁱ—Cu—N1'—C1'	−4.5 (9)
C3—C4—C5—C10	180.0	N1—Cu—N1'—C1'	−98.5 (14)
C4—C5—C6—C7	180.0	N1ⁱ—Cu—N1'—C1'	81.5 (14)
C10—C5—C6—C7	0.0	C11—N1'—C1'—C2'	111.9 (12)
C4—C5—C6—C1	0.0	Cu—N1'—C1'—C2'	−93.5 (9)
C10—C5—C6—C1	180.0	C11—N1'—C1'—C6'	−70.8 (15)
C2—C1—C6—C7	180.0	Cu—N1'—C1'—C6'	83.8 (10)
N1—C1—C6—C7	−5.0 (5)	C6'—C1'—C2'—C3'	0.0
C2—C1—C6—C5	0.0	N1'—C1'—C2'—C3'	177.3 (9)
N1—C1—C6—C5	175.0 (5)	C1'—C2'—C3'—C4'	0.0
C5—C6—C7—C8	0.0	C2'—C3'—C4'—C5'	0.0
C1—C6—C7—C8	180.0	C3'—C4'—C5'—C6'	0.0
C6—C7—C8—C9	0.0	C3'—C4'—C5'—C10'	180.0
C7—C8—C9—C10	0.0	C4'—C5'—C6'—C7'	180.0
C8—C9—C10—C5	0.0	C10'—C5'—C6'—C7'	0.0
C4—C5—C10—C9	180.0	C4'—C5'—C6'—C1'	0.0
C6—C5—C10—C9	0.0	C10'—C5'—C6'—C1'	180.0
C1—N1—C11—N1'	−97.8 (10)	C2'—C1'—C6'—C7'	180.0
Cu—N1—C11—N1'	72.5 (9)	N1'—C1'—C6'—C7'	2.8 (9)
C1—N1—C11—C12	167.1 (8)	C2'—C1'—C6'—C5'	0.0
Cu—N1—C11—C12	−22.6 (13)	N1'—C1'—C6'—C5'	−177.2 (9)
N1—C11—C12—C17	2.5 (14)	C5'—C6'—C7'—C8'	0.0
N1'—C11—C12—C17	−40.5 (13)	C1'—C6'—C7'—C8'	180.0
N1—C11—C12—C13	−171.2 (9)	C6'—C7'—C8'—C9'	0.0
N1'—C11—C12—C13	145.8 (9)	C7'—C8'—C9'—C10'	0.0
C17—C12—C13—C14	0.5 (9)	C8'—C9'—C10'—C5'	0.0
C11—C12—C13—C14	174.3 (7)	C6'—C5'—C10'—C9'	0.0
C12—C13—C14—C15	−1.6 (9)	C4'—C5'—C10'—C9'	180.0
C12—C13—C14—Br1	−179.9 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₇H₁₁BrNO)₂]
M_r	713.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.4572 (6), 9.5782 (3), 13.8108 (6)
β (°)	114.047 (5)
V (Å³)	1384.05 (10)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	4.78
Crystal size (mm)	0.25 × 0.20 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.381, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	15204, 2888, 2670
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.632

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.157, 1.10
No. of reflections	2888
No. of parameters	240
No. of restraints	69
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.95, −1.09

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Footnotes

‡Additional correspondence author, e-mail: shahverdizadeh@iaut.ac.ir.

Acknowledgements

We gratefully acknowledge support of this study by Tabriz Azad University, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM·C/HIR/MOHE/SC/12).

References

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