Dichloridobis[3-meth­oxy­methyl-4-phenyl-5-(2-pyrid­yl)-4H-1,2,4-triazole-κ2N1,N5]chromium(III) chloride

Jin, X.; Wang, Z.; Cao, S.

doi:10.1107/S1600536811039328

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1492

doi:10.1107/S1600536811039328

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Dichloridobis[3-methoxymethyl-4-phenyl-5-(2-pyridyl)-4H-1,2,4-triazole-κ²N¹,N⁵]chromium(III) chloride

Xiaofei Jin,^a Zuoxiang Wang ^a ^* and Shouping Cao ^a

^aSchool of Chemistry and Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: wangzx0908@yahoo.com.cn

(Received 19 July 2011; accepted 25 September 2011; online 5 October 2011)

In the title complex, [CrCl₂(C₁₅H₁₄N₄O)₂]Cl, the Cr^III atom is located on a twofold rotation axis and is coordinated by two N,N′-bidentate triazole derivatives and two chloride ions in a distorted octahedral CrN₂N′₂Cl₂ geometry. One of the two independent Cl⁻ counter-anions sits on a special position (site symmetry $[\overline{3}]$ .) and is fully occupied, whereas the other is disordered around a twofold rotation axis over two positions in a 2:3 ratio.

Related literature

For general background to the coordination chemistry of 1,2,4-triazole derivatives, see: Koningsbruggen et al. (1997 ); Garcia et al. (1999 ); Klingele & Brooker (2003 ); Matsukizono et al. (2008 ); Suksrichavalit et al. (2009 ); Rubio et al. (2011 ). For their biological activity, see: Tozkoparan et al. (2000 ); Grenman et al. (2003 ); Alagarsamy et al. (2008 ); Isloor et al. (2009 ).

Experimental

Crystal data

[CrCl₂(C₁₅H₁₄N₄O)₂]Cl
M_r = 690.95
Hexagonal, $[R \overline 3c ]$
a = 20.8852 (12) Å
c = 37.620 (4) Å
V = 14211.1 (19) Å³
Z = 18
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 296 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.896, T_max = 0.925
32255 measured reflections
2785 independent reflections
2243 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.119
S = 1.10
2785 reflections
213 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Selected bond lengths (Å)

Cr1—N1	2.040 (2)
Cr1—N4	2.0949 (19)
Cr1—Cl2ⁱ	2.2746 (7)
Symmetry code: (i) $[y+{\script{1\over 3}}, x-{\script{1\over 3}}, -z+{\script{1\over 6}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811039328/wm2515sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039328/wm2515Isup2.hkl

checkCIF report

Comment top

As the 1,2,4-triazole ring posesses strong electron donors, the coordination chemistry of 1,2,4-triazoles employed as ligand is widely studied (Koningsbruggen et al., 1997; Garcia et al., 1999; Klingele & Brooker, 2003; Matsukizono et al., 2008; Suksrichavalit et al., 2009; Rubio et al., 2011). Moreover, some 1,2,4-triazole compounds show biological activities (Tozkoparan et al., 2000; Grenman et al., 2003; Alagarsamy et al., 2008; Isloor et al., 2009). We report here the crystal structure analysis of the title compound, [Cr(C₁₅H₁₄N₄O)₂Cl₂]Cl.

In the title compouund, the chromium(III) atom is coordinated by two chelating 3-(methoxymethyl)-4-phenyl-5-(2-pyridyl)-4H-1,2,4- triazole ligands and two chloride anions in a distorted octahedral geometry with a CrN₂N'₂Cl₂ coordination set. The central Cr^III atom is located on a special position (site symmetry .2). The dihedral angle between the 1,2,4-triazole ring and the phenyl ring is 83.28 (16) °. One of the two non-coordinating Cl^- counter is located on a special position (site symmetry 3.) whereas the other shows disorder around a twofold rotation axis.

Related literature top

For general background to the coordination chemistry of 1,2,4-triazole derivatives, see: Koningsbruggen et al. (1997); Garcia et al. (1999); Klingele & Brooker (2003); Matsukizono et al. (2008); Suksrichavalit et al. (2009); Rubio et al. (2011). For their biological activity, see: Tozkoparan et al. (2000); Grenman et al. (2003); Alagarsamy et al. (2008); Isloor et al. (2009).

Experimental top

To a warm solution of 0.798 g of 3-(methoxymethyl)-4-phenyl-5-(2-pyridyl)-4H-1,2,4- triazole (3 mmol) in 20 ml ethanol, 0.399 g of CrCl₃^.6H₂O (1.5 mmol) were added. The filtrate was left to stand at room temperature for several days. The dark purple product was collected, and single crystals suitable for X-ray diffraction were selected.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atomic labelling. Displacement ellipsoids are shown at 30% probability level. [Symmetry code: A) y + 1/3, x - 1/3, -z + 1/6.]

Dichloridobis[3-methoxymethyl-4-phenyl-5-(2-pyridyl)-4H-1,2,4- triazole-κ²N¹,N⁵]chromium(III) chloride top

Crystal data top

[CrCl₂(C₁₅H₁₄N₄O)₂]Cl	D_x = 1.453 Mg m⁻³
M_r = 690.95	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3c	Cell parameters from 9999 reflections
Hall symbol: -R 3 2"c	θ = 2.4–21.0°
a = 20.8852 (12) Å	µ = 0.66 mm⁻¹
c = 37.620 (4) Å	T = 296 K
V = 14211.1 (19) Å³	Octahedral, purple
Z = 18	0.17 × 0.13 × 0.12 mm
F(000) = 6390

Data collection top

Bruker APEXII CCD diffractometer	2785 independent reflections
Radiation source: fine-focus sealed tube	2243 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −24→24
T_min = 0.896, T_max = 0.925	k = −24→24
32255 measured reflections	l = −44→42

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.072P)² + 5.702P] where P = (F_o² + 2F_c²)/3
2785 reflections	(Δ/σ)_max = 0.002
213 parameters	Δρ_max = 0.68 e Å⁻³
18 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[CrCl₂(C₁₅H₁₄N₄O)₂]Cl	Z = 18
M_r = 690.95	Mo Kα radiation
Hexagonal, R3c	µ = 0.66 mm⁻¹
a = 20.8852 (12) Å	T = 296 K
c = 37.620 (4) Å	0.17 × 0.13 × 0.12 mm
V = 14211.1 (19) Å³

Data collection top

Bruker APEXII CCD diffractometer	2785 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2243 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.925	R_int = 0.052
32255 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	18 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.10	Δρ_max = 0.68 e Å⁻³
2785 reflections	Δρ_min = −0.31 e Å⁻³
213 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	Occ. (<1)
C1	0.91830 (15)	0.47477 (15)	0.03037 (7)	0.0461 (6)
Cl1	1.0000	1.0000	0.0000	0.0778 (6)
Cl2	1.12055 (4)	0.71828 (4)	0.055158 (18)	0.0496 (2)
Cl3	0.7438 (5)	0.4643 (3)	0.07589 (15)	0.109 (2)	0.249 (5)
Cl3A	0.7727 (7)	0.4394 (7)	0.0833	0.113 (5)	0.168 (10)
Cr1	1.01043 (2)	0.67710 (2)	0.0833	0.03157 (19)
N1	0.96416 (11)	0.58203 (11)	0.05415 (5)	0.0386 (5)
O1	0.94481 (13)	0.37801 (11)	0.03630 (6)	0.0668 (6)
C2	0.92596 (13)	0.58194 (13)	0.02635 (6)	0.0363 (6)
N2	0.96048 (13)	0.51506 (11)	0.05722 (6)	0.0467 (6)
C3	0.92437 (13)	0.64891 (13)	0.01735 (6)	0.0369 (6)
N3	0.89587 (12)	0.51482 (11)	0.01048 (5)	0.0408 (5)
C4	0.89089 (15)	0.65933 (16)	−0.01212 (7)	0.0484 (7)
H4	0.8639	0.6207	−0.0278	0.058*
N4	0.96271 (10)	0.70375 (10)	0.04105 (5)	0.0345 (5)
C5	0.89817 (16)	0.72790 (16)	−0.01779 (8)	0.0533 (7)
H5	0.8766	0.7362	−0.0376	0.064*
C6	0.93721 (16)	0.78347 (16)	0.00588 (8)	0.0504 (7)
H6	0.9428	0.8301	0.0023	0.060*
C7	0.96843 (14)	0.76974 (14)	0.03532 (7)	0.0421 (6)
H7	0.9942	0.8076	0.0516	0.051*
C8	0.84783 (14)	0.49011 (14)	−0.02045 (7)	0.0413 (6)
C9	0.77403 (16)	0.46556 (15)	−0.01567 (8)	0.0521 (7)
H9	0.7551	0.4630	0.0070	0.062*
C10	0.72852 (18)	0.44481 (16)	−0.04488 (9)	0.0598 (8)
H10	0.6785	0.4287	−0.0421	0.072*
C11	0.7567 (2)	0.44776 (17)	−0.07810 (9)	0.0631 (9)
H11	0.7258	0.4332	−0.0978	0.076*
C12	0.8305 (2)	0.47214 (18)	−0.08231 (8)	0.0617 (9)
H12	0.8491	0.4741	−0.1050	0.074*
C13	0.87821 (17)	0.49400 (17)	−0.05344 (7)	0.0538 (7)
H13	0.9283	0.5105	−0.0562	0.065*
C14	0.8939 (2)	0.39585 (17)	0.02282 (9)	0.0651 (9)
H14A	0.8459	0.3644	0.0336	0.078*
H14B	0.8890	0.3874	−0.0026	0.078*
C15	0.9149 (2)	0.30032 (18)	0.04022 (9)	0.0744 (10)
H15A	0.9495	0.2911	0.0527	0.112*
H15B	0.9054	0.2776	0.0172	0.112*
H15C	0.8695	0.2799	0.0534	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0529 (16)	0.0402 (14)	0.0461 (15)	0.0241 (13)	−0.0090 (12)	−0.0049 (12)
Cl1	0.0920 (10)	0.0920 (10)	0.0494 (11)	0.0460 (5)	0.000	0.000
Cl2	0.0408 (4)	0.0593 (4)	0.0460 (4)	0.0230 (3)	0.0107 (3)	0.0075 (3)
Cl3	0.162 (5)	0.081 (3)	0.074 (3)	0.053 (3)	0.008 (3)	−0.008 (2)
Cl3A	0.121 (5)	0.121 (5)	0.089 (6)	0.053 (5)	0.013 (4)	−0.013 (4)
Cr1	0.0317 (2)	0.0317 (2)	0.0285 (3)	0.0137 (2)	−0.00026 (11)	0.00026 (11)
N1	0.0433 (12)	0.0364 (11)	0.0357 (11)	0.0195 (10)	−0.0063 (9)	−0.0019 (9)
O1	0.0815 (15)	0.0456 (12)	0.0795 (15)	0.0364 (11)	−0.0167 (12)	−0.0035 (10)
C2	0.0354 (13)	0.0355 (13)	0.0348 (13)	0.0153 (11)	−0.0035 (10)	−0.0025 (10)
N2	0.0570 (14)	0.0368 (12)	0.0464 (13)	0.0235 (11)	−0.0147 (11)	−0.0052 (10)
C3	0.0333 (13)	0.0402 (14)	0.0353 (13)	0.0170 (11)	−0.0017 (10)	0.0000 (11)
N3	0.0444 (12)	0.0385 (12)	0.0380 (12)	0.0195 (10)	−0.0119 (9)	−0.0077 (9)
C4	0.0507 (16)	0.0506 (16)	0.0436 (15)	0.0250 (13)	−0.0131 (12)	0.0004 (12)
N4	0.0347 (10)	0.0347 (11)	0.0320 (11)	0.0156 (9)	0.0018 (8)	0.0025 (8)
C5	0.0549 (17)	0.0564 (18)	0.0526 (17)	0.0309 (15)	−0.0099 (14)	0.0084 (14)
C6	0.0580 (17)	0.0441 (15)	0.0540 (18)	0.0293 (14)	0.0019 (14)	0.0102 (13)
C7	0.0449 (14)	0.0373 (14)	0.0443 (15)	0.0206 (12)	0.0012 (12)	0.0021 (11)
C8	0.0453 (15)	0.0389 (14)	0.0414 (15)	0.0222 (12)	−0.0119 (12)	−0.0096 (11)
C9	0.0483 (16)	0.0450 (16)	0.0565 (18)	0.0184 (13)	−0.0061 (13)	−0.0083 (13)
C10	0.0513 (17)	0.0476 (17)	0.077 (2)	0.0219 (14)	−0.0214 (16)	−0.0115 (15)
C11	0.076 (2)	0.0477 (17)	0.072 (2)	0.0359 (17)	−0.0394 (18)	−0.0169 (15)
C12	0.096 (3)	0.066 (2)	0.0365 (16)	0.0504 (19)	−0.0136 (16)	−0.0093 (13)
C13	0.0610 (18)	0.0626 (19)	0.0467 (17)	0.0375 (16)	−0.0064 (14)	−0.0079 (14)
C14	0.079 (2)	0.0469 (17)	0.074 (2)	0.0345 (17)	−0.0306 (18)	−0.0187 (15)
C15	0.117 (3)	0.058 (2)	0.056 (2)	0.049 (2)	−0.001 (2)	0.0027 (15)

Geometric parameters (Å, º) top

C1—N2	1.328 (3)	C5—C6	1.363 (4)
C1—N3	1.368 (3)	C5—H5	0.9300
C1—C14	1.489 (4)	C6—C7	1.386 (4)
Cl2—Cr1	2.2747 (7)	C6—H6	0.9300
Cl3—Cl3ⁱ	2.028 (19)	C7—H7	0.9300
Cr1—N1ⁱ	2.040 (2)	C8—C9	1.371 (4)
Cr1—N1	2.040 (2)	C8—C13	1.378 (4)
Cr1—N4ⁱ	2.0948 (19)	C9—C10	1.374 (4)
Cr1—N4	2.0949 (19)	C9—H9	0.9300
Cr1—Cl2ⁱ	2.2746 (7)	C10—C11	1.370 (4)
N1—C2	1.315 (3)	C10—H10	0.9300
N1—N2	1.367 (3)	C11—C12	1.369 (5)
O1—C14	1.387 (4)	C11—H11	0.9300
O1—C15	1.425 (4)	C12—C13	1.387 (4)
C2—N3	1.355 (3)	C12—H12	0.9300
C2—C3	1.456 (3)	C13—H13	0.9300
C3—N4	1.353 (3)	C14—H14A	0.9700
C3—C4	1.384 (3)	C14—H14B	0.9700
N3—C8	1.452 (3)	C15—H15A	0.9600
C4—C5	1.379 (4)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
N4—C7	1.340 (3)

N2—C1—N3	110.5 (2)	C6—C5—H5	120.3
N2—C1—C14	126.8 (2)	C4—C5—H5	120.3
N3—C1—C14	122.7 (2)	C5—C6—C7	119.3 (3)
N1ⁱ—Cr1—N1	87.33 (12)	C5—C6—H6	120.4
N1ⁱ—Cr1—N4ⁱ	78.06 (8)	C7—C6—H6	120.4
N1—Cr1—N4ⁱ	93.14 (8)	N4—C7—C6	122.1 (2)
N1ⁱ—Cr1—N4	93.15 (8)	N4—C7—H7	118.9
N1—Cr1—N4	78.06 (8)	C6—C7—H7	118.9
N4ⁱ—Cr1—N4	167.94 (10)	C9—C8—C13	122.6 (3)
N1ⁱ—Cr1—Cl2ⁱ	90.84 (6)	C9—C8—N3	118.4 (2)
N1—Cr1—Cl2ⁱ	172.01 (6)	C13—C8—N3	119.0 (2)
N4ⁱ—Cr1—Cl2ⁱ	94.08 (5)	C8—C9—C10	119.0 (3)
N4—Cr1—Cl2ⁱ	94.29 (6)	C8—C9—H9	120.5
N1ⁱ—Cr1—Cl2	172.01 (6)	C10—C9—H9	120.5
N1—Cr1—Cl2	90.83 (6)	C11—C10—C9	120.1 (3)
N4ⁱ—Cr1—Cl2	94.29 (6)	C11—C10—H10	120.0
N4—Cr1—Cl2	94.07 (5)	C9—C10—H10	120.0
Cl2ⁱ—Cr1—Cl2	92.02 (4)	C12—C11—C10	120.1 (3)
C2—N1—N2	110.0 (2)	C12—C11—H11	120.0
C2—N1—Cr1	114.91 (16)	C10—C11—H11	120.0
N2—N1—Cr1	135.02 (15)	C11—C12—C13	121.4 (3)
C14—O1—C15	112.6 (3)	C11—C12—H12	119.3
N1—C2—N3	108.6 (2)	C13—C12—H12	119.3
N1—C2—C3	119.3 (2)	C8—C13—C12	116.9 (3)
N3—C2—C3	132.1 (2)	C8—C13—H13	121.5
C1—N2—N1	105.3 (2)	C12—C13—H13	121.6
N4—C3—C4	121.7 (2)	O1—C14—C1	110.1 (2)
N4—C3—C2	111.8 (2)	O1—C14—H14A	109.6
C4—C3—C2	126.4 (2)	C1—C14—H14A	109.6
C2—N3—C1	105.6 (2)	O1—C14—H14B	109.6
C2—N3—C8	127.0 (2)	C1—C14—H14B	109.6
C1—N3—C8	127.4 (2)	H14A—C14—H14B	108.2
C5—C4—C3	119.0 (3)	O1—C15—H15A	109.5
C5—C4—H4	120.5	O1—C15—H15B	109.5
C3—C4—H4	120.5	H15A—C15—H15B	109.5
C7—N4—C3	118.4 (2)	O1—C15—H15C	109.5
C7—N4—Cr1	125.86 (17)	H15A—C15—H15C	109.5
C3—N4—Cr1	115.74 (15)	H15B—C15—H15C	109.5
C6—C5—C4	119.4 (3)

Symmetry code: (i) y+1/3, x−1/3, −z+1/6.

Experimental details

Crystal data
Chemical formula	[CrCl₂(C₁₅H₁₄N₄O)₂]Cl
M_r	690.95
Crystal system, space group	Hexagonal, R3c
Temperature (K)	296
a, c (Å)	20.8852 (12), 37.620 (4)
V (Å³)	14211.1 (19)
Z	18
Radiation type	Mo Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.17 × 0.13 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.896, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	32255, 2785, 2243
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.119, 1.10
No. of reflections	2785
No. of parameters	213
No. of restraints	18
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.31

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cr1—N1	2.040 (2)	Cr1—Cl2ⁱ	2.2746 (7)
Cr1—N4	2.0949 (19)

Symmetry code: (i) y+1/3, x−1/3, −z+1/6.

Acknowledgements

We are grateful to Jingye Pharmochemical Pilot Plant for financial assistance though project 8507040052.

References

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