{2,6-Bis[(4-bromo­phen­yl)imino­meth­yl]pyridine-κ3N,N′,N′′}trichlorido­chromium(III)

Li, X.-P.; Liu, Y.-Y.; Zhao, J.-S.

doi:10.1107/S1600536810034689

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1215

doi:10.1107/S1600536810034689

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{2,6-Bis[(4-bromophenyl)iminomethyl]pyridine-κ³N,N′,N′′}trichloridochromium(III)

Xiao-Ping Li,^a Yong-Yong Liu ^a and Jian-She Zhao ^a ^*

^aDepartment of Chemistry, Shaanxi Key Laboratory for Physico-Inorganic Chemistry, Northwest University, Xi'an 710069, People's Republic of China
^*Correspondence e-mail: jszhao@nwu.edu.cn

(Received 26 August 2010; accepted 28 August 2010; online 8 September 2010)

In the title compound, [CrCl₃(C₁₉H₁₃Br₂N₃)], the Cr³⁺ion is coordinated by the tridentate 2,6-bis[(4-bromophenyl)iminomethyl]pyridine Schiff base ligand in a fac-octahedral 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_r = 601.49
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.153
S = 0.97
4177 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034689/ng5023sup1.cif

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

checkCIF report

Comment top

Schiff bases have often been used as chelating ligands in coordination chemistry (Yin et al. (2010); Yang et al. (2010); Rohini et al. (2009): Legrand et al. (2009)). We report here the crystal structure of the title new chromium complex with the chelating Schiff base ligand 2, 6-bis [1-(4-bromophenylimino)] pyridine The Cr atom in the complex is six-coordinated by one pyridine N and two imine N atoms of the Schiff base ligand, and by two bromide atoms, forming tetrahedral geometry (Fig.1). The dihedral angle between the pyridine and the benzene rings is 23.9 (6) ° and 70.7 (1) °. The bond lengths (Table 1) related to the Cr atom are comparable to those observed in similar chromium complexes (Sugiyama et al. (2002); Sun et al. (2009); Gong et al. (2009); Xiao et al. (2010)).

Related literature top

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 top

2,6-bis[1-(4-bromophenylimino)]pyridine(0.0226 g, 0.05 mmol), and CrCl₃?6H₂O (0.0139 g, 0.05 mmol) were mixed and stirred in ethanol(10 ml) for 2 min and then heated in a stainless steel reactor with Teflon liner at 353 K for 72 h. After cooling at 5 K per hour, green crystals were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex, showing 50% probability displacement ellipsoids.

{2,6-Bis[(4-bromophenyl)iminomethyl]pyridine- κ³N,N',N''}trichloridochromium(III) top

Crystal data top

[CrCl₃(C₁₉H₁₃Br₂N₃)]	F(000) = 1172
M_r = 601.49	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0769P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
4177 reflections	Δρ_max = 0.61 e Å⁻³
254 parameters	Δρ_min = −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)

Crystal data top

[CrCl₃(C₁₉H₁₃Br₂N₃)]	V = 2156.4 (7) Å³
M_r = 601.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.722 (3) Å	µ = 4.62 mm⁻¹
b = 10.111 (2) Å	T = 296 K
c = 18.905 (3) Å	0.20 × 0.13 × 0.09 mm
β = 124.702 (12)°

Data collection top

Bruker APEXII CCD diffractometer	4177 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2279 reflections with I > 2σ(I)
T_min = 0.457, T_max = 0.689	R_int = 0.053
11189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 0.97	Δρ_max = 0.61 e Å⁻³
4177 reflections	Δρ_min = −0.41 e Å⁻³
254 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[CrCl₃(C₁₉H₁₃Br₂N₃)]
M_r	601.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.722 (3), 10.111 (2), 18.905 (3)
β (°)	124.702 (12)
V (Å³)	2156.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.62
Crystal size (mm)	0.20 × 0.13 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.457, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	11189, 4177, 2279
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.153, 0.97
No. of reflections	4177
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.41

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the NWU Graduate Experimental Research Funds (project No. 09YSY22) for financial support.

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