[4-Bromo-N-(pyridin-2-yl­methyl­idene)aniline-κ2N,N′]iodido(triphenyl­phosphane-κP)copper(I)

Khalaji, A.D.; Bahramian, B.; Jafari, K.; Fejfarová, K.; Dušek, M.

doi:10.1107/S160053681202884X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m1001-m1002

https://doi.org/10.1107/S160053681202884X

Open

access

[4-Bromo-N-(pyridin-2-ylmethylidene)aniline-κ²N,N′]iodido(triphenylphosphane-κP)copper(I)

Aliakbar Dehno Khalaji,^a Bahram Bahramian,^b Khadijeh Jafari,^b Karla Fejfarová ^c ^* and Michal Dušek ^c

^aDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran, ^bCollege of Chemistry, Shahrood University of Technology, Shahrood, Iran, and ^cInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: fejfarov@fzu.cz

(Received 20 June 2012; accepted 25 June 2012; online 30 June 2012)

In the title compound, [CuI(C₁₂H₉BrN₂)(C₁₈H₁₅P)], the Cu^I ion is bonded to one I atom, one triphenylphosphane P atom and two N atoms of the diimine ligand in a distorted tetrahedral geometry. The Schiff base acts as a chelating ligand and coordinates to the Cu^I atom via two N atoms. In the diimine ligand, the dihedral angle between the pyridine and bromophenyl rings is 19.2 (2)°. In the crystal, molecules are connected by π–π stacking interactions between inversion-related pyridine rings [centroid–centroid distance = 3.404 (3) Å].

Related literature

For related structures and their applications, see: Dehghanpour et al. (2006 , 2008 ); Saha et al. (2010 , 2011a ,b ); Habibi et al. (2007 ); Morshedi et al. (2009 ); Al-Fayez et al. (2007 ); Kickelbick et al. (2003 ); Massa et al. (2009 ); Chen et al. (2012 ); Roy et al. (2011 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

[CuI(C₁₂H₉BrN₂)(C₁₈H₁₅P)]
M_r = 713.9
Monoclinic, P 2₁ /c
a = 10.3141 (5) Å
b = 34.7124 (16) Å
c = 8.3792 (4) Å
β = 114.321 (6)°
V = 2733.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 3.47 mm⁻¹
T = 120 K
0.49 × 0.04 × 0.03 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.914, T_max = 1.000
14996 measured reflections
5893 independent reflections
4325 reflections with I > 3σ(I)
R_int = 0.048

Refinement

R[F² > 3σ(F²)] = 0.038
wR(F²) = 0.110
S = 1.19
5893 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Selected bond lengths (Å)

I1—Cu1	2.6386 (7)
Cu1—P1	2.2065 (15)
Cu1—N1	2.119 (5)
Cu1—N2	2.080 (4)

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681202884X/pk2426sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202884X/pk2426Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of copper(I) complexes with bidentate diimine ligands, such as bipyridine and phenanthroline, has received much attention over the last decade due to the many applications of these complexes (Dehghanpour et al., 2006; Saha et al., 2010, 2011a, 2011b; Habibi et al., 2007). Effort has been devoted to design and synthesis of new Schiff base ligands to control the geometry and properties of copper(I) complexes (Morshedi et al., 2009). Most of the studies have been on tetrahedral copper(I) complexes of the type [Cu(LL)₂]⁺ and Cu(LL)P₂]⁺ where LL is a diimine and P is a phosphane (Massa et al., 2009; Dehghanpour et al., 2008; Chen et al., 2012; Roy et al., 2011). Although reports of copper(I) complexes are numerous, limited work has been done on mixed ligand copper(I) complexes of the type [Cu(Schiff base)PX] (X= Cl, Br, I) (Dehghanpour et al., 2006; Saha et al., 2010, 2011a, 2011b; Habibi et al., 2007; Morshedi et al., 2009; Al-Fayez et al., 2007; Kickelbick et al., 2003). This study is a part of our ongoing efforts to synthesize and characterize copper(I) complexes with bidentate Schiff base ligands.

The molecular structure with the atom-numbering scheme is presented in Fig. 1, and the bond lengths (Allen et al., 1987) and angles are generally normal. The copper(I) is coordinated by two nitrogen atoms of the bidentate Schiff-base ligand, one P atom of triphenylphosphane and one I atom. Although a tetrahedral geometry might be expected for a four coordinate copper(I) centre, the geometry around the copper(I) ion is distorted by the restricting bite angle N1—Cu1—N2 [79.3 (2)°] of the chelating Schiff-base ligand.

Related literature top

For related structures and their applications, see: Dehghanpour et al. (2006, 2008); Saha et al. (2010, 2011a,b); Habibi et al. (2007); Morshedi et al. (2009); Al-Fayez et al. (2007); Kickelbick et al. (2003); Massa et al. (2009); Chen et al. (2012); Roy et al. (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental top

To a stirring solution of 190 mg (1 mmol) CuI in 5 ml of acetonitrile was added dropwise 263 mg (1 mmol) of triphenylphosphane in 5 ml acetonitrile. The mixture was stirred for 30 min and then 261 mg (1 mmol) of ligand, 4-bromophenylpyridine-2-ylmethyleneamine, in 10 ml acetonitrile was added and stirred for an additional 20 min. The volume of the solvent was reduced under vacuum to about 5 ml. The diffusion of diethyl ether vapor into the concentration solution gave dark red crystals. The crystals were filtered off and washed with Et₂O. Yield: 65%. Anal. Calc. for C₃₀H₂₄N₂CuPBrI: C, 50.48; H, 3.38; N, 3.93%. Found: C, 50.55; H, 3.51; N, 3.78%.

Structure description top

For related structures and their applications, see: Dehghanpour et al. (2006, 2008); Saha et al. (2010, 2011a,b); Habibi et al. (2007); Morshedi et al. (2009); Al-Fayez et al. (2007); Kickelbick et al. (2003); Massa et al. (2009); Chen et al. (2012); Roy et al. (2011). For standard bond lengths, see: Allen et al. (1987).

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: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

[4-Bromo-N-(pyridin-2-ylmethylidene)aniline- κ²N,N']iodido(triphenylphosphane-κP)copper(I) top

Crystal data top

[CuI(C₁₂H₉BrN₂)(C₁₈H₁₅P)]	F(000) = 1400
M_r = 713.9	D_x = 1.734 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 5306 reflections
a = 10.3141 (5) Å	θ = 2.9–27.0°
b = 34.7124 (16) Å	µ = 3.47 mm⁻¹
c = 8.3792 (4) Å	T = 120 K
β = 114.321 (6)°	Needle, red
V = 2733.7 (3) Å³	0.49 × 0.04 × 0.03 mm
Z = 4

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	5893 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4325 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 10.4 pixels mm^-1	θ_max = 27.2°, θ_min = 2.9°
Rotation method data acquisition using ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −44→43
T_min = 0.914, T_max = 1.000	l = −10→10
14996 measured reflections

Refinement top

Refinement on F²	96 constraints
R[F > 3σ(F)] = 0.038	H-atom parameters constrained
wR(F) = 0.110	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0016I²)
S = 1.19	(Δ/σ)_max = 0.028
5893 reflections	Δρ_max = 0.70 e Å⁻³
325 parameters	Δρ_min = −0.65 e Å⁻³
0 restraints

Crystal data top

[CuI(C₁₂H₉BrN₂)(C₁₈H₁₅P)]	V = 2733.7 (3) Å³
M_r = 713.9	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3141 (5) Å	µ = 3.47 mm⁻¹
b = 34.7124 (16) Å	T = 120 K
c = 8.3792 (4) Å	0.49 × 0.04 × 0.03 mm
β = 114.321 (6)°

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	5893 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4325 reflections with I > 3σ(I)
T_min = 0.914, T_max = 1.000	R_int = 0.048
14996 measured reflections

Refinement top

R[F > 3σ(F)] = 0.038	0 restraints
wR(F) = 0.110	H-atom parameters constrained
S = 1.19	Δρ_max = 0.70 e Å⁻³
5893 reflections	Δρ_min = −0.65 e Å⁻³
325 parameters

Special details top

Experimental. CrysAlisPro (Agilent, 2010) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

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

	x	y	z	U_iso*/U_eq
I1	0.78044 (3)	0.068800 (9)	0.72718 (4)	0.02639 (13)
Cu1	0.59846 (6)	0.079263 (17)	0.39909 (7)	0.0238 (2)
Br1	1.00314 (6)	0.252746 (15)	0.34867 (7)	0.0330 (2)
P1	0.41099 (13)	0.11517 (4)	0.35881 (16)	0.0221 (4)
N1	0.7265 (4)	0.09533 (11)	0.2668 (5)	0.0210 (14)
N2	0.6081 (4)	0.02740 (12)	0.2802 (5)	0.0239 (15)
C1	0.7562 (5)	0.06704 (13)	0.1899 (6)	0.0246 (18)
C2	0.6948 (5)	0.02930 (14)	0.1929 (6)	0.0249 (17)
C3	0.7260 (5)	−0.00216 (14)	0.1148 (6)	0.0277 (18)
C4	0.6666 (5)	−0.03762 (15)	0.1227 (6)	0.032 (2)
C5	0.5758 (5)	−0.03981 (15)	0.2079 (6)	0.0315 (19)
C6	0.5512 (5)	−0.00660 (14)	0.2856 (6)	0.0275 (18)
C7	0.7877 (5)	0.13217 (14)	0.2721 (6)	0.0229 (17)
C8	0.8508 (5)	0.14430 (14)	0.1607 (6)	0.029 (2)
C9	0.9133 (5)	0.18024 (15)	0.1828 (6)	0.030 (2)
C10	0.9110 (5)	0.20401 (14)	0.3131 (6)	0.0259 (18)
C11	0.8463 (5)	0.19317 (14)	0.4213 (6)	0.0292 (19)
C12	0.7854 (5)	0.15713 (14)	0.4002 (6)	0.0257 (18)
C13	0.4456 (5)	0.16036 (14)	0.4825 (6)	0.0247 (18)
C14	0.5628 (5)	0.16325 (14)	0.6392 (6)	0.0270 (19)
C15	0.5972 (5)	0.19795 (15)	0.7293 (7)	0.033 (2)
C16	0.5145 (6)	0.23034 (15)	0.6643 (7)	0.035 (2)
C17	0.3958 (6)	0.22751 (15)	0.5099 (7)	0.037 (2)
C18	0.3608 (6)	0.19342 (14)	0.4189 (7)	0.033 (2)
C19	0.3142 (5)	0.13315 (13)	0.1366 (6)	0.0246 (18)
C20	0.3927 (5)	0.15205 (14)	0.0564 (6)	0.0274 (19)
C21	0.3251 (5)	0.16944 (14)	−0.1052 (6)	0.029 (2)
C22	0.1783 (5)	0.16791 (14)	−0.1889 (6)	0.031 (2)
C23	0.1010 (5)	0.14853 (14)	−0.1132 (6)	0.0285 (19)
C24	0.1677 (5)	0.13116 (14)	0.0487 (6)	0.0271 (19)
C25	0.2723 (5)	0.09130 (14)	0.4047 (6)	0.0235 (17)
C26	0.2011 (5)	0.10822 (14)	0.4975 (6)	0.0248 (18)
C27	0.0987 (5)	0.08829 (14)	0.5314 (6)	0.0255 (18)
C28	0.0620 (5)	0.05149 (14)	0.4687 (6)	0.0265 (18)
C29	0.1315 (5)	0.03393 (15)	0.3733 (6)	0.030 (2)
C30	0.2352 (5)	0.05376 (14)	0.3424 (6)	0.0263 (19)
H1	0.81789	0.070579	0.131067	0.0295*
H3	0.787927	0.000399	0.055749	0.0332*
H4	0.687643	−0.060078	0.070836	0.0387*
H5	0.53086	−0.063714	0.212969	0.0378*
H6	0.490079	−0.008491	0.346082	0.033*
H8	0.85054	0.127607	0.069147	0.0346*
H9	0.95784	0.188549	0.108178	0.0365*
H11	0.843766	0.210414	0.509557	0.0351*
H12	0.740691	0.149188	0.475133	0.0308*
H14	0.621452	0.141025	0.686939	0.0324*
H15	0.679671	0.199445	0.838399	0.0399*
H16	0.539722	0.254385	0.726113	0.0422*
H17	0.33634	0.249691	0.46463	0.0447*
H18	0.277444	0.192115	0.310656	0.0391*
H20	0.494659	0.152842	0.114923	0.0329*
H21	0.379189	0.182424	−0.158621	0.0346*
H22	0.129947	0.180362	−0.300197	0.0375*
H23	−0.000701	0.147118	−0.173989	0.0341*
H24	0.112699	0.117791	0.099932	0.0325*
H26	0.223603	0.134233	0.538479	0.0297*
H27	0.05353	0.100187	0.598676	0.0306*
H28	−0.010308	0.037787	0.48966	0.0318*
H29	0.106618	0.008169	0.329775	0.0359*
H30	0.282097	0.041643	0.277593	0.0315*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.03169 (19)	0.02779 (19)	0.02021 (17)	0.00070 (14)	0.01123 (14)	−0.00064 (12)
Cu1	0.0255 (3)	0.0265 (3)	0.0224 (3)	0.0003 (3)	0.0128 (3)	−0.0009 (2)
Br1	0.0418 (3)	0.0281 (3)	0.0311 (3)	−0.0068 (2)	0.0171 (3)	−0.0001 (2)
P1	0.0252 (6)	0.0227 (6)	0.0213 (6)	−0.0001 (5)	0.0125 (5)	−0.0004 (5)
N1	0.022 (2)	0.025 (2)	0.0164 (19)	0.0010 (17)	0.0088 (17)	−0.0026 (15)
N2	0.025 (2)	0.028 (2)	0.0180 (19)	0.0004 (18)	0.0078 (17)	0.0006 (16)
C1	0.024 (2)	0.032 (3)	0.020 (2)	0.006 (2)	0.012 (2)	0.0057 (19)
C2	0.024 (2)	0.032 (3)	0.015 (2)	0.001 (2)	0.004 (2)	0.0013 (19)
C3	0.031 (3)	0.030 (3)	0.022 (2)	0.003 (2)	0.010 (2)	−0.001 (2)
C4	0.045 (3)	0.028 (3)	0.020 (2)	0.005 (2)	0.010 (2)	−0.004 (2)
C5	0.033 (3)	0.026 (3)	0.027 (3)	−0.002 (2)	0.004 (2)	0.001 (2)
C6	0.027 (3)	0.029 (3)	0.021 (2)	−0.003 (2)	0.005 (2)	0.0006 (19)
C7	0.022 (2)	0.028 (3)	0.019 (2)	0.001 (2)	0.009 (2)	0.0023 (19)
C8	0.040 (3)	0.029 (3)	0.022 (3)	0.001 (2)	0.018 (2)	−0.002 (2)
C9	0.035 (3)	0.035 (3)	0.027 (3)	0.000 (2)	0.019 (2)	0.002 (2)
C10	0.028 (3)	0.026 (3)	0.022 (2)	−0.001 (2)	0.008 (2)	0.0009 (19)
C11	0.037 (3)	0.030 (3)	0.023 (2)	−0.002 (2)	0.016 (2)	−0.005 (2)
C12	0.029 (3)	0.030 (3)	0.022 (2)	−0.002 (2)	0.013 (2)	−0.0013 (19)
C13	0.029 (3)	0.026 (3)	0.024 (2)	−0.003 (2)	0.016 (2)	−0.0022 (19)
C14	0.030 (3)	0.028 (3)	0.028 (3)	0.001 (2)	0.017 (2)	−0.002 (2)
C15	0.031 (3)	0.039 (3)	0.031 (3)	−0.005 (2)	0.013 (2)	−0.007 (2)
C16	0.043 (3)	0.023 (3)	0.045 (3)	−0.003 (2)	0.024 (3)	−0.008 (2)
C17	0.043 (3)	0.022 (3)	0.047 (3)	0.000 (2)	0.018 (3)	−0.004 (2)
C18	0.036 (3)	0.028 (3)	0.034 (3)	−0.001 (2)	0.016 (3)	−0.001 (2)
C19	0.035 (3)	0.019 (2)	0.024 (2)	0.002 (2)	0.015 (2)	−0.0018 (18)
C20	0.027 (3)	0.028 (3)	0.030 (3)	−0.002 (2)	0.014 (2)	0.004 (2)
C21	0.038 (3)	0.026 (3)	0.030 (3)	0.004 (2)	0.021 (2)	0.003 (2)
C22	0.043 (3)	0.031 (3)	0.020 (2)	0.010 (2)	0.012 (2)	0.002 (2)
C23	0.029 (3)	0.031 (3)	0.025 (3)	0.001 (2)	0.010 (2)	−0.004 (2)
C24	0.032 (3)	0.028 (3)	0.025 (3)	0.001 (2)	0.015 (2)	−0.002 (2)
C25	0.025 (2)	0.027 (3)	0.019 (2)	−0.002 (2)	0.009 (2)	0.0028 (18)
C26	0.029 (3)	0.024 (3)	0.022 (2)	0.000 (2)	0.011 (2)	0.0003 (18)
C27	0.025 (2)	0.031 (3)	0.024 (2)	0.002 (2)	0.013 (2)	−0.001 (2)
C28	0.023 (2)	0.031 (3)	0.025 (2)	−0.005 (2)	0.009 (2)	0.003 (2)
C29	0.035 (3)	0.023 (3)	0.032 (3)	0.001 (2)	0.013 (2)	−0.003 (2)
C30	0.029 (3)	0.026 (3)	0.026 (3)	0.002 (2)	0.014 (2)	−0.003 (2)

Geometric parameters (Å, º) top

I1—Cu1	2.6386 (7)	C13—C18	1.408 (7)
Cu1—P1	2.2065 (15)	C14—C15	1.388 (7)
Cu1—N1	2.119 (5)	C14—H14	0.96
Cu1—N2	2.080 (4)	C15—C16	1.380 (7)
Br1—C10	1.903 (5)	C15—H15	0.96
P1—C13	1.832 (5)	C16—C17	1.370 (7)
P1—C19	1.823 (4)	C16—H16	0.96
P1—C25	1.826 (6)	C17—C18	1.373 (7)
N1—C1	1.279 (7)	C17—H17	0.96
N1—C7	1.419 (6)	C18—H18	0.96
N2—C2	1.371 (7)	C19—C20	1.409 (8)
N2—C6	1.327 (6)	C19—C24	1.384 (7)
C1—C2	1.460 (7)	C20—C21	1.381 (6)
C1—H1	0.96	C20—H20	0.96
C2—C3	1.377 (7)	C21—C22	1.383 (7)
C3—C4	1.388 (7)	C21—H21	0.96
C3—H3	0.96	C22—C23	1.382 (9)
C4—C5	1.394 (9)	C22—H22	0.96
C4—H4	0.96	C23—C24	1.381 (6)
C5—C6	1.398 (8)	C23—H23	0.96
C5—H5	0.96	C24—H24	0.96
C6—H6	0.96	C25—C26	1.399 (8)
C7—C8	1.405 (8)	C25—C30	1.397 (7)
C7—C12	1.387 (7)	C26—C27	1.386 (8)
C8—C9	1.381 (7)	C26—H26	0.96
C8—H8	0.96	C27—C28	1.374 (7)
C9—C10	1.377 (8)	C27—H27	0.96
C9—H9	0.96	C28—C29	1.413 (8)
C10—C11	1.381 (8)	C28—H28	0.96
C11—C12	1.378 (7)	C29—C30	1.384 (8)
C11—H11	0.96	C29—H29	0.96
C12—H12	0.96	C30—H30	0.96
C13—C14	1.374 (6)

I1—Cu1—P1	116.08 (4)	P1—C13—C14	119.5 (4)
I1—Cu1—N1	104.61 (8)	P1—C13—C18	122.6 (3)
I1—Cu1—N2	103.06 (9)	C14—C13—C18	117.8 (4)
P1—Cu1—N1	117.84 (11)	C13—C14—C15	120.7 (4)
P1—Cu1—N2	128.86 (10)	C13—C14—H14	119.66
N1—Cu1—N2	79.31 (17)	C15—C14—H14	119.6609
Cu1—P1—C13	116.28 (16)	C14—C15—C16	121.0 (4)
Cu1—P1—C19	115.2 (2)	C14—C15—H15	119.5162
Cu1—P1—C25	115.14 (16)	C16—C15—H15	119.5164
C13—P1—C19	100.5 (2)	C15—C16—C17	118.7 (5)
C13—P1—C25	104.8 (3)	C15—C16—H16	120.6387
C19—P1—C25	102.9 (2)	C17—C16—H16	120.6398
Cu1—N1—C1	113.1 (3)	C16—C17—C18	121.0 (5)
Cu1—N1—C7	125.9 (3)	C16—C17—H17	119.5157
C1—N1—C7	120.8 (5)	C18—C17—H17	119.5157
Cu1—N2—C2	112.6 (3)	C13—C18—C17	120.8 (4)
Cu1—N2—C6	130.1 (4)	C13—C18—H18	119.5977
C2—N2—C6	117.1 (4)	C17—C18—H18	119.598
N1—C1—C2	119.0 (5)	P1—C19—C20	117.8 (3)
N1—C1—H1	120.4965	P1—C19—C24	123.0 (4)
C2—C1—H1	120.4972	C20—C19—C24	119.1 (4)
N2—C2—C1	115.8 (5)	C19—C20—C21	120.9 (5)
N2—C2—C3	123.1 (5)	C19—C20—H20	119.5623
C1—C2—C3	121.1 (5)	C21—C20—H20	119.5601
C2—C3—C4	119.1 (6)	C20—C21—C22	119.1 (5)
C2—C3—H3	120.4409	C20—C21—H21	120.4332
C4—C3—H3	120.442	C22—C21—H21	120.4324
C3—C4—C5	118.4 (5)	C21—C22—C23	120.3 (4)
C3—C4—H4	120.8107	C21—C22—H22	119.8737
C5—C4—H4	120.8119	C23—C22—H22	119.8726
C4—C5—C6	118.9 (5)	C22—C23—C24	121.0 (5)
C4—C5—H5	120.5658	C22—C23—H23	119.4855
C6—C5—H5	120.566	C24—C23—H23	119.4861
N2—C6—C5	123.4 (6)	C19—C24—C23	119.6 (5)
N2—C6—H6	118.315	C19—C24—H24	120.2034
C5—C6—H6	118.317	C23—C24—H24	120.2026
N1—C7—C8	124.8 (4)	P1—C25—C26	124.2 (4)
N1—C7—C12	116.0 (5)	P1—C25—C30	117.5 (4)
C8—C7—C12	119.2 (5)	C26—C25—C30	118.3 (5)
C7—C8—C9	120.0 (5)	C25—C26—C27	121.5 (4)
C7—C8—H8	120.0129	C25—C26—H26	119.2398
C9—C8—H8	120.0148	C27—C26—H26	119.2411
C8—C9—C10	119.2 (6)	C26—C27—C28	119.9 (5)
C8—C9—H9	120.3841	C26—C27—H27	120.0454
C10—C9—H9	120.3841	C28—C27—H27	120.0454
Br1—C10—C9	119.1 (4)	C27—C28—C29	119.6 (5)
Br1—C10—C11	119.0 (4)	C27—C28—H28	120.2082
C9—C10—C11	121.9 (5)	C29—C28—H28	120.2108
C10—C11—C12	118.7 (5)	C28—C29—C30	120.2 (5)
C10—C11—H11	120.6268	C28—C29—H29	119.904
C12—C11—H11	120.6295	C30—C29—H29	119.9041
C7—C12—C11	120.9 (5)	C25—C30—C29	120.5 (5)
C7—C12—H12	119.5252	C25—C30—H30	119.7526
C11—C12—H12	119.5264	C29—C30—H30	119.7517

Experimental details

Crystal data
Chemical formula	[CuI(C₁₂H₉BrN₂)(C₁₈H₁₅P)]
M_r	713.9
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	10.3141 (5), 34.7124 (16), 8.3792 (4)
β (°)	114.321 (6)
V (Å³)	2733.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.47
Crystal size (mm)	0.49 × 0.04 × 0.03

Data collection
Diffractometer	Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.914, 1.000
No. of measured, independent and observed [I > 3σ(I)] reflections	14996, 5893, 4325
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F > 3σ(F)], wR(F), S	0.038, 0.110, 1.19
No. of reflections	5893
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.65

Computer programs: CrysAlis PRO (Agilent, 2010), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).

Selected bond lengths (Å) top

I1—Cu1	2.6386 (7)	Cu1—N1	2.119 (5)
Cu1—P1	2.2065 (15)	Cu1—N2	2.080 (4)

Acknowledgements

We acknowledge Golestan University and Shahrood University of Technology for partial support of this work, the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae Project of the Academy of Sciences of the Czech Republic.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Al-Fayez, S., Abdel-Rahman, L. H., Shemsi, A. M., Seddigi, Z. S. & Fettouhi, M. (2007). J. Chem. Crystallogr. 37, 517–521. CAS Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Chen, J.-L., Cao, X.-F., Gu, W., Su, B.-T., Zhang, F., Wen, H.-R. & Hong, R. (2012). Inorg. Chem. Commun. 15, 65–68. Web of Science CSD CrossRef Google Scholar
Dehghanpour, S., Fotouhi, L., Mohammadpour Amini, M., Khavasi, H. R., Jahani, K., Nouroozi, F. & Zamanifar, E. (2008). J. Coord. Chem. 61, 455–463. Web of Science CSD CrossRef CAS Google Scholar
Dehghanpour, S., Mahmoudkhani, A. H. & Amirnasr, M. (2006). Struct. Chem. 17, 255–262. Web of Science CSD CrossRef CAS Google Scholar
Habibi, M. H., Montazerozohori, M., Barati, K., Harrington, R. W. & Clegg, W. (2007). Anal. Sci. 23, x45–x46. CAS Google Scholar
Kickelbick, G., Amirnasr, M., Khalaji, A. D. & Dehghanpour, S. (2003). Aust. J. Chem. 56, 323–328. Web of Science CSD CrossRef CAS Google Scholar
Massa, W., Dehghanpour, S. & Jahani, K. (2009). Inorg. Chim. Acta, 362, 2872–2878. Web of Science CSD CrossRef CAS Google Scholar
Morshedi, M., Amirnasr, M., Slawin, A. M. Z., Woollins, J. D. & Khalaji, A. D. (2009). Polyhedron, 28, 167–171. Web of Science CSD CrossRef CAS Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic. Google Scholar
Roy, S., Mondal, T. K., Mitra, P., Torres, E. L. & Sinha, S. (2011). Polyhedron, 30, 913–922. Web of Science CSD CrossRef CAS Google Scholar
Saha, G., Datta, P., Sarkar, K. K., Saha, R., Mostafa, G. & Sinha, C. (2011a). Polyhedron, 30, 614–623. Web of Science CSD CrossRef CAS Google Scholar
Saha, G., Sarkar, K. K., Datta, P., Raghavaiah, P. & Sinha, C. (2010). Polyhedron, 29, 2098–2104. Web of Science CSD CrossRef CAS Google Scholar
Saha, G., Sarkar, K. K., Mondal, T. K. & Sinha, C. (2011b). Inorg. Chim. Acta, 387, 240–247. Web of Science CSD CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.