Chlorido{2-[1-(2-pyridylmethyl-imino)eth-yl]pyrrolato-κN,N',N''}copper(II).

The potential tridentate Schiff base ligand 2-[1-(2-pyridyl-methyl-imino)eth-yl]pyrrole (HL) was synthesized from the condensation of 2-acetyl-pyrrole with 2-amino-methyl-pyridine. The title compound, [Cu(C(12)H(12)N(3))Cl], was synthesized from HL and copper(II) chloride using triethyl-amine as a base to deprotonate the pyrrole NH group. The title compound is a monomer and the central copper(II) ion is bound to three N atoms of the deprotonated tridentate ligand and to one chloride ion in a square-planar N(3)Cl coordination.

Related literature

For related literature, see: Bertrand & Kirkwood (1972 ▶); Brooker & Carter (1995 ▶); Brown et al. (1988 ▶); Garland et al. (1996 ▶).

Experimental

Crystal data

[Cu(C12H12N3)Cl]

M = 297.24

Monoclinic,

a = 8.830 (2) Å

b = 7.2806 (15) Å

c = 18.750 (4) Å

β = 100.448 (4)°

V = 1185.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.05 mm−1

T = 213 (2) K

0.24 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.642, T max = 0.719

11059 measured reflections

2164 independent reflections

1840 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.124

S = 1.05

2164 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006934/hg2384sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006934/hg2384Isup2.hkl

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

[Cu(C12H12N3)Cl]	F000 = 604
Mr = 297.24	Dx = 1.666 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 3740 reflections
a = 8.830 (2) Å	θ = 2.1–25.6º
b = 7.2806 (15) Å	µ = 2.05 mm−1
c = 18.750 (4) Å	T = 213 (2) K
β = 100.448 (4)º	Block, green
V = 1185.4 (4) Å3	0.24 × 0.18 × 0.16 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2164 independent reflections
Radiation source: sealed tube	1840 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
T = 213(2) K	θmax = 25.4º
φ and ω scans	θmin = 3.0º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.642, Tmax = 0.719	k = −7→8
11059 measured reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.06P)2 + 1.99P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2164 reflections	Δρmax = 0.38 e Å−3
156 parameters	Δρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cu1	0.50155 (6)	0.79633 (7)	0.42653 (3)	0.0312 (2)
Cl1	0.64180 (13)	0.80713 (16)	0.33884 (6)	0.0431 (3)
N1	0.6561 (4)	0.6909 (5)	0.5025 (2)	0.0378 (9)
N2	0.3797 (4)	0.7939 (5)	0.50388 (19)	0.0331 (8)
N3	0.3055 (4)	0.9028 (5)	0.37105 (17)	0.0303 (8)
C1	0.8039 (6)	0.6345 (6)	0.5150 (3)	0.0479 (12)
H1	0.8685	0.6360	0.4810	0.057*
C2	0.8452 (7)	0.5741 (8)	0.5857 (3)	0.0648 (16)
H2	0.9412	0.5291	0.6073	0.078*
C3	0.7176 (7)	0.5928 (7)	0.6184 (3)	0.0593 (15)
H3	0.7107	0.5626	0.6659	0.071*
C4	0.6022 (6)	0.6658 (6)	0.5659 (2)	0.0423 (11)
C5	0.4452 (6)	0.7218 (6)	0.5646 (2)	0.0413 (11)
C6	0.2223 (5)	0.8562 (6)	0.4865 (2)	0.0374 (10)
H6A	0.2082	0.9629	0.5156	0.045*
H6B	0.1534	0.7601	0.4970	0.045*
C7	0.1863 (5)	0.9048 (6)	0.4073 (2)	0.0327 (9)
C8	0.0406 (5)	0.9525 (7)	0.3731 (3)	0.0434 (12)
H8	−0.0410	0.9485	0.3982	0.052*
C9	0.0156 (6)	1.0060 (7)	0.3019 (3)	0.0514 (13)
H9	−0.0829	1.0374	0.2783	0.062*
C10	0.1382 (6)	1.0128 (7)	0.2655 (3)	0.0471 (12)
H10	0.1249	1.0534	0.2178	0.057*
C11	0.2804 (5)	0.9580 (6)	0.3018 (2)	0.0371 (10)
H11	0.3628	0.9593	0.2771	0.045*
C12	0.3689 (7)	0.6982 (7)	0.6292 (3)	0.0551 (14)
H12A	0.2995	0.7987	0.6315	0.083*
H12B	0.4458	0.6960	0.6725	0.083*
H12C	0.3124	0.5849	0.6249	0.083*

	U11	U22	U33	U12	U13	U23
Cu1	0.0315 (3)	0.0342 (3)	0.0282 (3)	−0.0016 (2)	0.0058 (2)	0.0003 (2)
Cl1	0.0374 (6)	0.0497 (7)	0.0463 (7)	0.0016 (5)	0.0183 (5)	0.0013 (5)
N1	0.038 (2)	0.032 (2)	0.039 (2)	−0.0039 (16)	−0.0028 (17)	0.0009 (16)
N2	0.044 (2)	0.0289 (18)	0.0278 (19)	−0.0009 (16)	0.0090 (16)	−0.0006 (15)
N3	0.0331 (18)	0.0318 (18)	0.0275 (18)	−0.0058 (16)	0.0094 (15)	−0.0027 (15)
C1	0.043 (3)	0.037 (3)	0.057 (3)	−0.003 (2)	−0.010 (2)	−0.007 (2)
C2	0.065 (4)	0.051 (3)	0.064 (4)	0.008 (3)	−0.028 (3)	−0.009 (3)
C3	0.094 (4)	0.035 (3)	0.036 (3)	0.005 (3)	−0.022 (3)	−0.002 (2)
C4	0.066 (3)	0.025 (2)	0.032 (2)	−0.003 (2)	−0.003 (2)	−0.0036 (18)
C5	0.066 (3)	0.025 (2)	0.034 (2)	−0.008 (2)	0.010 (2)	−0.0033 (19)
C6	0.045 (3)	0.036 (2)	0.037 (2)	−0.005 (2)	0.021 (2)	−0.001 (2)
C7	0.038 (2)	0.031 (2)	0.031 (2)	−0.0075 (19)	0.0108 (18)	−0.0060 (19)
C8	0.033 (2)	0.050 (3)	0.048 (3)	−0.004 (2)	0.011 (2)	−0.005 (2)
C9	0.036 (3)	0.057 (3)	0.056 (3)	0.006 (2)	−0.003 (2)	−0.009 (3)
C10	0.053 (3)	0.053 (3)	0.031 (2)	−0.003 (2)	−0.002 (2)	−0.002 (2)
C11	0.034 (2)	0.047 (3)	0.031 (2)	−0.004 (2)	0.0074 (19)	−0.005 (2)
C12	0.094 (4)	0.042 (3)	0.032 (3)	−0.005 (3)	0.018 (3)	0.004 (2)

Cu1—N1	1.943 (4)	C4—C5	1.441 (7)
Cu1—N2	1.956 (3)	C5—C12	1.499 (7)
Cu1—N3	2.006 (3)	C6—C7	1.503 (6)
Cu1—Cl1	2.2319 (12)	C6—H6A	0.9700
N1—C1	1.347 (6)	C6—H6B	0.9700
N1—C4	1.370 (6)	C7—C8	1.374 (6)
N2—C5	1.291 (6)	C8—C9	1.369 (7)
N2—C6	1.442 (6)	C8—H8	0.9300
N3—C11	1.339 (5)	C9—C10	1.381 (7)
N3—C7	1.354 (5)	C9—H9	0.9300
C1—C2	1.381 (7)	C10—C11	1.374 (6)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.384 (8)	C11—H11	0.9300
C2—H2	0.9300	C12—H12A	0.9600
C3—C4	1.388 (7)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
N1—Cu1—N2	81.98 (16)	C4—C5—C12	121.7 (4)
N1—Cu1—N3	163.31 (15)	N2—C6—C7	108.7 (3)
N2—Cu1—N3	81.33 (14)	N2—C6—H6A	110.0
N1—Cu1—Cl1	98.29 (12)	C7—C6—H6A	110.0
N2—Cu1—Cl1	178.47 (10)	N2—C6—H6B	110.0
N3—Cu1—Cl1	98.40 (10)	C7—C6—H6B	110.0
C1—N1—C4	106.6 (4)	H6A—C6—H6B	108.3
C1—N1—Cu1	141.0 (4)	N3—C7—C8	121.0 (4)
C4—N1—Cu1	112.4 (3)	N3—C7—C6	116.7 (4)
C5—N2—C6	125.9 (4)	C8—C7—C6	122.3 (4)
C5—N2—Cu1	116.0 (3)	C9—C8—C7	119.9 (4)
C6—N2—Cu1	117.8 (3)	C9—C8—H8	120.0
C11—N3—C7	118.5 (4)	C7—C8—H8	120.0
C11—N3—Cu1	126.5 (3)	C8—C9—C10	119.3 (5)
C7—N3—Cu1	114.8 (3)	C8—C9—H9	120.3
N1—C1—C2	110.1 (5)	C10—C9—H9	120.3
N1—C1—H1	125.0	C11—C10—C9	118.2 (5)
C2—C1—H1	125.0	C11—C10—H10	120.9
C1—C2—C3	107.4 (5)	C9—C10—H10	120.9
C1—C2—H2	126.3	N3—C11—C10	122.9 (4)
C3—C2—H2	126.3	N3—C11—H11	118.6
C2—C3—C4	105.9 (5)	C10—C11—H11	118.6
C2—C3—H3	127.0	C5—C12—H12A	109.5
C4—C3—H3	127.0	C5—C12—H12B	109.5
N1—C4—C3	109.9 (5)	H12A—C12—H12B	109.5
N1—C4—C5	115.6 (4)	C5—C12—H12C	109.5
C3—C4—C5	134.5 (5)	H12A—C12—H12C	109.5
N2—C5—C4	113.9 (4)	H12B—C12—H12C	109.5
N2—C5—C12	124.3 (5)

Cu1—N1	1.943 (4)
Cu1—N2	1.956 (3)
Cu1—N3	2.006 (3)
Cu1—Cl1	2.2319 (12)

N1—Cu1—N2	81.98 (16)
N1—Cu1—N3	163.31 (15)
N2—Cu1—N3	81.33 (14)
N1—Cu1—Cl1	98.29 (12)
N2—Cu1—Cl1	178.47 (10)
N3—Cu1—Cl1	98.40 (10)