{2,6-Bis[(4-bromo-phen-yl)imino-meth-yl]pyridine-κN,N',N''}trichlorido-chromium(III).

In the title compound, [CrCl(3)(C(19)H(13)Br(2)N(3))], the Cr(3+ )ion is coordinated by the tridentate 2,6-bis-[(4-bromo-phen-yl)imino-meth-yl]pyridine Schiff base ligand in a fac-octa-hedral geometry. The dihedral angles between the pyridine and benzene rings are 23.9 (6) and 70.7 (1)°.

Related literature

For background to Schiff bases as chelating ligands, see: Yin et al. (2010 ▶); Yang et al. (2010 ▶); Barboiu et al. (2009 ▶); Rohini et al. (2009 ▶); Legrand et al. (2009 ▶). For similar zinc complexes, see: Ceniceros-Gomez et al. (2000 ▶); Sugiyama et al. (2002 ▶); Sun et al. (2009 ▶); Gong et al. (2009 ▶); Xiao et al. (2010 ▶).

Experimental

Crystal data

[CrCl3(C19H13Br2N3)]

M = 601.49

Monoclinic,

a = 13.722 (3) Å

b = 10.111 (2) Å

c = 18.905 (3) Å

β = 124.702 (12)°

V = 2156.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 4.62 mm−1

T = 296 K

0.20 × 0.13 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.457, T max = 0.689

11189 measured reflections

4177 independent reflections

2279 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.153

S = 0.97

4177 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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/S1600536810034689/ng5023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034689/ng5023Isup2.hkl

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

[CrCl3(C19H13Br2N3)]	F(000) = 1172
Mr = 601.49	Dx = 1.853 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1555 reflections
a = 13.722 (3) Å	θ = 2.4–19.9°
b = 10.111 (2) Å	µ = 4.62 mm−1
c = 18.905 (3) Å	T = 296 K
β = 124.702 (12)°	Block, green
V = 2156.4 (7) Å3	0.20 × 0.13 × 0.09 mm
Z = 4

Bruker APEXII CCD diffractometer	4177 independent reflections
Radiation source: fine-focus sealed tube	2279 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 25.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→13
Tmin = 0.457, Tmax = 0.689	k = −12→12
11189 measured reflections	l = −23→23

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.0769P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
4177 reflections	Δρmax = 0.61 e Å−3
254 parameters	Δρmin = −0.41 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0012 (4)

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
Cr1	0.28797 (8)	0.86124 (8)	0.64659 (6)	0.0434 (3)
Br1	0.69677 (8)	0.65971 (9)	1.11306 (5)	0.0892 (3)
Br2	0.00271 (10)	0.39656 (7)	0.26880 (5)	0.1018 (4)
Cl1	0.31007 (19)	0.63611 (14)	0.66454 (12)	0.0757 (6)
Cl2	0.44502 (15)	0.87626 (17)	0.63412 (11)	0.0630 (5)
Cl3	0.12377 (15)	0.86383 (17)	0.65121 (11)	0.0656 (5)
N1	0.3903 (4)	0.9528 (4)	0.7728 (3)	0.0483 (12)
N2	0.2615 (4)	1.0541 (4)	0.6191 (3)	0.0449 (11)
N3	0.1766 (4)	0.8645 (4)	0.5113 (3)	0.0463 (12)
C1	0.4323 (7)	0.7618 (7)	0.8620 (4)	0.0691 (19)
H1	0.3679	0.7197	0.8145	0.083*
C2	0.5019 (8)	0.6955 (7)	0.9398 (5)	0.077 (2)
H2	0.4839	0.6084	0.9440	0.092*
C3	0.5961 (6)	0.7561 (7)	1.0101 (4)	0.0632 (18)
C4	0.6215 (6)	0.8848 (7)	1.0040 (4)	0.071 (2)
H4	0.6850	0.9269	1.0522	0.085*
C5	0.5537 (6)	0.9535 (7)	0.9267 (4)	0.0658 (18)
H5	0.5721	1.0407	0.9232	0.079*
C6	0.4597 (5)	0.8921 (6)	0.8557 (4)	0.0480 (14)
C7	0.3845 (6)	1.0794 (6)	0.7687 (4)	0.0560 (16)
H7	0.4241	1.1302	0.8185	0.067*
C8	0.3151 (5)	1.1420 (5)	0.6847 (4)	0.0501 (15)
C9	0.2975 (6)	1.2779 (6)	0.6666 (4)	0.0571 (17)
H9	0.3329	1.3398	0.7109	0.069*
C10	0.2260 (6)	1.3180 (6)	0.5810 (4)	0.0591 (17)
H10	0.2134	1.4078	0.5680	0.071*
C11	0.1731 (5)	1.2261 (6)	0.5144 (4)	0.0531 (16)
H11	0.1258	1.2530	0.4573	0.064*
C12	0.1932 (5)	1.0924 (5)	0.5360 (3)	0.0424 (13)
C13	0.1483 (5)	0.9800 (6)	0.4780 (4)	0.0480 (14)
H13	0.1007	0.9917	0.4187	0.058*
C14	0.1391 (5)	0.7505 (5)	0.4560 (3)	0.0436 (14)
C15	0.1856 (6)	0.7279 (6)	0.4095 (4)	0.0498 (15)
H15	0.2436	0.7837	0.4152	0.060*
C16	0.1458 (7)	0.6218 (6)	0.3541 (4)	0.0623 (19)
H16	0.1769	0.6053	0.3222	0.075*
C17	0.0601 (7)	0.5402 (6)	0.3461 (4)	0.0626 (19)
C18	0.0162 (7)	0.5603 (7)	0.3942 (5)	0.077 (2)
H18	−0.0405	0.5031	0.3891	0.092*
C19	0.0562 (6)	0.6658 (6)	0.4505 (5)	0.070 (2)
H19	0.0277	0.6796	0.4842	0.084*

	U11	U22	U33	U12	U13	U23
Cr1	0.0463 (6)	0.0347 (5)	0.0413 (5)	−0.0011 (4)	0.0203 (5)	−0.0050 (4)
Br1	0.0738 (6)	0.1233 (8)	0.0643 (5)	0.0183 (5)	0.0356 (5)	0.0310 (5)
Br2	0.1720 (11)	0.0517 (5)	0.0608 (5)	−0.0254 (5)	0.0540 (6)	−0.0206 (4)
Cl1	0.1130 (17)	0.0359 (9)	0.0707 (12)	0.0020 (9)	0.0479 (12)	−0.0021 (8)
Cl2	0.0507 (10)	0.0704 (11)	0.0663 (11)	0.0064 (9)	0.0324 (9)	0.0027 (8)
Cl3	0.0572 (11)	0.0812 (12)	0.0614 (10)	−0.0099 (9)	0.0355 (9)	−0.0088 (9)
N1	0.055 (3)	0.037 (3)	0.044 (3)	−0.002 (2)	0.023 (3)	−0.006 (2)
N2	0.047 (3)	0.036 (3)	0.042 (3)	−0.001 (2)	0.020 (2)	−0.005 (2)
N3	0.047 (3)	0.041 (3)	0.041 (3)	−0.004 (2)	0.018 (3)	−0.007 (2)
C1	0.070 (5)	0.064 (4)	0.055 (4)	−0.006 (4)	0.024 (4)	−0.001 (4)
C2	0.098 (6)	0.056 (4)	0.067 (5)	−0.003 (4)	0.041 (5)	0.010 (4)
C3	0.058 (5)	0.077 (5)	0.047 (4)	0.013 (4)	0.026 (4)	0.004 (4)
C4	0.061 (5)	0.086 (5)	0.046 (4)	−0.012 (4)	0.019 (4)	−0.010 (4)
C5	0.059 (4)	0.065 (4)	0.049 (4)	−0.011 (4)	0.017 (4)	0.000 (3)
C6	0.045 (4)	0.046 (3)	0.047 (4)	0.002 (3)	0.022 (3)	−0.002 (3)
C7	0.058 (4)	0.053 (4)	0.044 (4)	−0.002 (3)	0.021 (3)	−0.011 (3)
C8	0.048 (4)	0.039 (3)	0.049 (4)	−0.004 (3)	0.020 (3)	−0.006 (3)
C9	0.060 (4)	0.038 (3)	0.054 (4)	0.002 (3)	0.022 (4)	−0.002 (3)
C10	0.066 (5)	0.030 (3)	0.071 (5)	−0.003 (3)	0.033 (4)	−0.002 (3)
C11	0.049 (4)	0.042 (3)	0.058 (4)	0.002 (3)	0.024 (3)	0.006 (3)
C12	0.043 (4)	0.036 (3)	0.042 (3)	−0.002 (3)	0.020 (3)	−0.005 (3)
C13	0.042 (4)	0.054 (4)	0.040 (3)	−0.006 (3)	0.019 (3)	−0.010 (3)
C14	0.047 (4)	0.042 (3)	0.033 (3)	−0.005 (3)	0.017 (3)	−0.009 (3)
C15	0.063 (4)	0.042 (3)	0.046 (4)	−0.004 (3)	0.033 (3)	−0.002 (3)
C16	0.097 (6)	0.044 (4)	0.057 (4)	0.003 (4)	0.050 (4)	0.001 (3)
C17	0.094 (6)	0.040 (3)	0.036 (3)	0.002 (4)	0.026 (4)	−0.002 (3)
C18	0.079 (5)	0.060 (5)	0.077 (5)	−0.024 (4)	0.036 (5)	−0.023 (4)
C19	0.068 (5)	0.066 (5)	0.084 (5)	−0.016 (4)	0.048 (5)	−0.021 (4)

Cr1—N2	1.997 (4)	C5—H5	0.9300
Cr1—N3	2.105 (5)	C7—C8	1.451 (8)
Cr1—N1	2.170 (5)	C7—H7	0.9300
Cr1—Cl1	2.2959 (17)	C8—C9	1.403 (8)
Cr1—Cl2	2.3025 (19)	C9—C10	1.394 (8)
Cr1—Cl3	2.3042 (19)	C9—H9	0.9300
Br1—C3	1.893 (6)	C10—C11	1.391 (8)
Br2—C17	1.886 (6)	C10—H10	0.9300
N1—C7	1.283 (7)	C11—C12	1.393 (8)
N1—C6	1.428 (7)	C11—H11	0.9300
N2—C12	1.349 (7)	C12—C13	1.450 (7)
N2—C8	1.353 (7)	C13—H13	0.9300
N3—C13	1.277 (7)	C14—C15	1.369 (7)
N3—C14	1.439 (6)	C14—C19	1.379 (8)
C1—C2	1.387 (9)	C15—C16	1.377 (8)
C1—C6	1.394 (8)	C15—H15	0.9300
C1—H1	0.9300	C16—C17	1.372 (9)
C2—C3	1.363 (9)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.361 (9)
C3—C4	1.369 (9)	C18—C19	1.381 (8)
C4—C5	1.392 (9)	C18—H18	0.9300
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.370 (8)
N2—Cr1—N3	76.68 (18)	C1—C6—N1	117.1 (6)
N2—Cr1—N1	77.16 (18)	N1—C7—C8	118.8 (5)
N3—Cr1—N1	153.84 (18)	N1—C7—H7	120.6
N2—Cr1—Cl1	174.56 (14)	C8—C7—H7	120.6
N3—Cr1—Cl1	97.97 (13)	N2—C8—C9	119.5 (5)
N1—Cr1—Cl1	108.18 (14)	N2—C8—C7	113.1 (5)
N2—Cr1—Cl2	87.19 (14)	C9—C8—C7	127.4 (6)
N3—Cr1—Cl2	87.05 (14)	C10—C9—C8	118.5 (6)
N1—Cr1—Cl2	91.55 (14)	C10—C9—H9	120.7
Cl1—Cr1—Cl2	91.60 (7)	C8—C9—H9	120.7
N2—Cr1—Cl3	87.83 (14)	C11—C10—C9	121.1 (6)
N3—Cr1—Cl3	89.83 (14)	C11—C10—H10	119.5
N1—Cr1—Cl3	89.31 (14)	C9—C10—H10	119.5
Cl1—Cr1—Cl3	93.18 (7)	C10—C11—C12	118.0 (6)
Cl2—Cr1—Cl3	174.62 (7)	C10—C11—H11	121.0
C7—N1—C6	118.4 (5)	C12—C11—H11	121.0
C7—N1—Cr1	112.3 (4)	N2—C12—C11	120.7 (5)
C6—N1—Cr1	129.3 (4)	N2—C12—C13	111.7 (5)
C12—N2—C8	122.2 (5)	C11—C12—C13	127.6 (5)
C12—N2—Cr1	119.1 (4)	N3—C13—C12	117.7 (5)
C8—N2—Cr1	118.6 (4)	N3—C13—H13	121.2
C13—N3—C14	119.5 (5)	C12—C13—H13	121.2
C13—N3—Cr1	114.8 (4)	C15—C14—C19	120.9 (5)
C14—N3—Cr1	125.6 (4)	C15—C14—N3	119.7 (5)
C2—C1—C6	119.4 (7)	C19—C14—N3	119.4 (5)
C2—C1—H1	120.3	C14—C15—C16	119.4 (6)
C6—C1—H1	120.3	C14—C15—H15	120.3
C3—C2—C1	121.0 (7)	C16—C15—H15	120.3
C3—C2—H2	119.5	C17—C16—C15	119.7 (6)
C1—C2—H2	119.5	C17—C16—H16	120.1
C2—C3—C4	119.4 (6)	C15—C16—H16	120.1
C2—C3—Br1	120.2 (6)	C18—C17—C16	121.0 (6)
C4—C3—Br1	120.3 (6)	C18—C17—Br2	118.9 (5)
C3—C4—C5	120.9 (6)	C16—C17—Br2	120.1 (5)
C3—C4—H4	119.6	C17—C18—C19	119.8 (7)
C5—C4—H4	119.6	C17—C18—H18	120.1
C6—C5—C4	119.7 (6)	C19—C18—H18	120.1
C6—C5—H5	120.1	C14—C19—C18	119.2 (6)
C4—C5—H5	120.1	C14—C19—H19	120.4
C5—C6—C1	119.6 (6)	C18—C19—H19	120.4
C5—C6—N1	123.2 (5)
N2—Cr1—N1—C7	−0.1 (4)	C7—N1—C6—C5	−26.0 (9)
N3—Cr1—N1—C7	0.2 (7)	Cr1—N1—C6—C5	154.0 (5)
Cl1—Cr1—N1—C7	178.9 (4)	C7—N1—C6—C1	157.2 (6)
Cl2—Cr1—N1—C7	86.7 (4)	Cr1—N1—C6—C1	−22.8 (8)
Cl3—Cr1—N1—C7	−88.0 (4)	C6—N1—C7—C8	179.5 (5)
N2—Cr1—N1—C6	179.9 (5)	Cr1—N1—C7—C8	−0.6 (7)
N3—Cr1—N1—C6	−179.8 (4)	C12—N2—C8—C9	1.4 (9)
Cl1—Cr1—N1—C6	−1.1 (5)	Cr1—N2—C8—C9	−180.0 (4)
Cl2—Cr1—N1—C6	−93.3 (5)	C12—N2—C8—C7	−179.9 (5)
Cl3—Cr1—N1—C6	92.0 (5)	Cr1—N2—C8—C7	−1.3 (7)
N3—Cr1—N2—C12	−0.5 (4)	N1—C7—C8—N2	1.2 (8)
N1—Cr1—N2—C12	179.4 (4)	N1—C7—C8—C9	179.8 (6)
Cl1—Cr1—N2—C12	9.9 (19)	N2—C8—C9—C10	−0.7 (9)
Cl2—Cr1—N2—C12	87.2 (4)	C7—C8—C9—C10	−179.2 (6)
Cl3—Cr1—N2—C12	−90.8 (4)	C8—C9—C10—C11	−0.2 (10)
N3—Cr1—N2—C8	−179.1 (5)	C9—C10—C11—C12	0.4 (9)
N1—Cr1—N2—C8	0.8 (4)	C8—N2—C12—C11	−1.2 (8)
Cl1—Cr1—N2—C8	−168.7 (14)	Cr1—N2—C12—C11	−179.8 (4)
Cl2—Cr1—N2—C8	−91.5 (4)	C8—N2—C12—C13	178.6 (5)
Cl3—Cr1—N2—C8	90.5 (4)	Cr1—N2—C12—C13	0.0 (6)
N2—Cr1—N3—C13	0.9 (4)	C10—C11—C12—N2	0.2 (9)
N1—Cr1—N3—C13	0.6 (7)	C10—C11—C12—C13	−179.5 (6)
Cl1—Cr1—N3—C13	−178.1 (4)	C14—N3—C13—C12	−176.8 (5)
Cl2—Cr1—N3—C13	−86.9 (4)	Cr1—N3—C13—C12	−1.2 (7)
Cl3—Cr1—N3—C13	88.7 (4)	N2—C12—C13—N3	0.8 (7)
N2—Cr1—N3—C14	176.2 (5)	C11—C12—C13—N3	−179.4 (6)
N1—Cr1—N3—C14	175.9 (4)	C13—N3—C14—C15	67.8 (7)
Cl1—Cr1—N3—C14	−2.8 (4)	Cr1—N3—C14—C15	−107.2 (5)
Cl2—Cr1—N3—C14	88.4 (4)	C13—N3—C14—C19	−111.8 (7)
Cl3—Cr1—N3—C14	−96.0 (4)	Cr1—N3—C14—C19	73.1 (7)
C6—C1—C2—C3	0.3 (11)	C19—C14—C15—C16	2.3 (9)
C1—C2—C3—C4	0.8 (11)	N3—C14—C15—C16	−177.3 (5)
C1—C2—C3—Br1	−175.3 (5)	C14—C15—C16—C17	0.1 (9)
C2—C3—C4—C5	−1.1 (11)	C15—C16—C17—C18	−2.0 (10)
Br1—C3—C4—C5	174.9 (5)	C15—C16—C17—Br2	178.8 (5)
C3—C4—C5—C6	0.4 (10)	C16—C17—C18—C19	1.5 (11)
C4—C5—C6—C1	0.7 (10)	Br2—C17—C18—C19	−179.3 (5)
C4—C5—C6—N1	−176.0 (6)	C15—C14—C19—C18	−2.9 (10)
C2—C1—C6—C5	−1.0 (10)	N3—C14—C19—C18	176.8 (6)
C2—C1—C6—N1	175.9 (6)	C17—C18—C19—C14	0.9 (11)