[4-Bromo-N-(pyridin-2-yl-methyl-idene)aniline-κ(2)N,N']iodido(triphenyl-phosphane-κP)copper(I).

In the title compound, [CuI(C(12)H(9)BrN(2))(C(18)H(15)P)], the Cu(I) ion is bonded to one I atom, one triphenyl-phosphane P atom and two N atoms of the diimine ligand in a distorted tetra-hedral 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 bromo-phenyl rings is 19.2 (2)°. In the crystal, mol-ecules are connected by π-π stacking inter-actions 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 = 713.9

Monoclinic,

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[F 2 > 3σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 1.19

5893 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.65 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202884X/pk2426sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202884X/pk2426Isup2.hkl

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

[CuI(C12H9BrN2)(C18H15P)]	F(000) = 1400
Mr = 713.9	Dx = 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

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	Rint = 0.048
Detector resolution: 10.4 pixels mm-1	θmax = 27.2°, θmin = 2.9°
Rotation method data acquisition using ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −44→43
Tmin = 0.914, Tmax = 1.000	l = −10→10
14996 measured reflections

Refinement on F2	96 constraints
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 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	Δρmax = 0.70 e Å−3
325 parameters	Δρmin = −0.65 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)