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ISSN: 2056-9890

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

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 CrIII 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[Koningsbruggen, P. J., Hassnoot, J. G., Kooijman, H., Reedijk, J. & Spek, A. L. (1997). Inorg. Chem. 36, 2487-2489.]); Garcia et al. (1999[Garcia, Y., Kahn, O., Rabardel, L., Chansou, B., Salmon, L. & Tuchagues, J. P. (1999). Inorg. Chem. 38, 4663-4670.]); Klingele & Brooker (2003[Klingele, M. H. & Brooker, S. (2003). Coord. Chem. Rev. 241, 119-132.]); Matsukizono et al. (2008[Matsukizono, H., Kuroiwa, K. & Kimizuka, N. (2008). Chem. Lett. 37, 446-447.]); Suksrichavalit et al. (2009[Suksrichavalit, T., Prachayasittikul, S., Nantasenamat, C., Isarankurai-Na-Ayudhyal, C. & Prachayasittikul, V. (2009). Eur. J. Med. Chem. 44, 3259-3265.]); Rubio et al. (2011[Rubio, M., Hernández, R., Nogales, A., Roig, A. & López, D. (2011). Eur. Polym. J. 47, 52-60.]). For their biological activity, see: Tozkoparan et al. (2000[Tozkoparan, B., Gokhan, N., Aktay, G., Yesilada, E. & Ertana, M. (2000). Eur. J. Med. Chem. 35, 743-750.]); Grenman et al. (2003[Grenman, H., Salmi, T., Mäki-Arvela, J., Eränen, K., Tirronen, E. & Pehkonen, A. (2003). Org. Process Res. Dev. 7, 942-950.]); Alagarsamy et al. (2008[Alagarsamy, V., Rupeshkumar, M., Kavitha, K., Meena, S., Shankar, D., Siddiqui, A. A. & Rajesh, R. (2008). Eur. J. Med. Chem. 43, 2331-2337.]); Isloor et al. (2009[Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.]).

[Scheme 1]

Experimental

Crystal data
  • [CrCl2(C15H14N4O)2]Cl

  • Mr = 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[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.896, Tmax = 0.925

  • 32255 measured reflections

  • 2785 independent reflections

  • 2243 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.68 e Å−3

  • Δρmin = −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[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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 CrIII 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.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded, riding with C—H = 0.93 Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene), with Uiso(H) = 1.2 or 1.5 times Ueq(C). Atom CL3 is positionally and occupationally disordered around a twofold rotation axis. One part (Cl3A, site occupation factor 0.168 (10)) sits on the twofold axis whereas the other part (Cl3) is 1.014 (19) Å away from this atom with a s.o.f. of 0.249 (5). To achieve an electroneutral compound, the overall occuipancy of the two Cl3 atoms was restrained to 0.3.

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
[Figure 1] 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]ClDx = 1.453 Mg m3
Mr = 690.95Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3cCell parameters from 9999 reflections
Hall symbol: -R 3 2"cθ = 2.4–21.0°
a = 20.8852 (12) ŵ = 0.66 mm1
c = 37.620 (4) ÅT = 296 K
V = 14211.1 (19) Å3Octahedral, purple
Z = 180.17 × 0.13 × 0.12 mm
F(000) = 6390
Data collection top
Bruker APEXII CCD
diffractometer
2785 independent reflections
Radiation source: fine-focus sealed tube2243 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2424
Tmin = 0.896, Tmax = 0.925k = 2424
32255 measured reflectionsl = 4442
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.072P)2 + 5.702P]
where P = (Fo2 + 2Fc2)/3
2785 reflections(Δ/σ)max = 0.002
213 parametersΔρmax = 0.68 e Å3
18 restraintsΔρmin = 0.31 e Å3
Crystal data top
[CrCl2(C15H14N4O)2]ClZ = 18
Mr = 690.95Mo Kα radiation
Hexagonal, R3cµ = 0.66 mm1
a = 20.8852 (12) ÅT = 296 K
c = 37.620 (4) Å0.17 × 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)
Tmin = 0.896, Tmax = 0.925Rint = 0.052
32255 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03918 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.10Δρmax = 0.68 e Å3
2785 reflectionsΔρmin = 0.31 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.91830 (15)0.47477 (15)0.03037 (7)0.0461 (6)
Cl11.00001.00000.00000.0778 (6)
Cl21.12055 (4)0.71828 (4)0.055158 (18)0.0496 (2)
Cl30.7438 (5)0.4643 (3)0.07589 (15)0.109 (2)0.249 (5)
Cl3A0.7727 (7)0.4394 (7)0.08330.113 (5)0.168 (10)
Cr11.01043 (2)0.67710 (2)0.08330.03157 (19)
N10.96416 (11)0.58203 (11)0.05415 (5)0.0386 (5)
O10.94481 (13)0.37801 (11)0.03630 (6)0.0668 (6)
C20.92596 (13)0.58194 (13)0.02635 (6)0.0363 (6)
N20.96048 (13)0.51506 (11)0.05722 (6)0.0467 (6)
C30.92437 (13)0.64891 (13)0.01735 (6)0.0369 (6)
N30.89587 (12)0.51482 (11)0.01048 (5)0.0408 (5)
C40.89089 (15)0.65933 (16)0.01212 (7)0.0484 (7)
H40.86390.62070.02780.058*
N40.96271 (10)0.70375 (10)0.04105 (5)0.0345 (5)
C50.89817 (16)0.72790 (16)0.01779 (8)0.0533 (7)
H50.87660.73620.03760.064*
C60.93721 (16)0.78347 (16)0.00588 (8)0.0504 (7)
H60.94280.83010.00230.060*
C70.96843 (14)0.76974 (14)0.03532 (7)0.0421 (6)
H70.99420.80760.05160.051*
C80.84783 (14)0.49011 (14)0.02045 (7)0.0413 (6)
C90.77403 (16)0.46556 (15)0.01567 (8)0.0521 (7)
H90.75510.46300.00700.062*
C100.72852 (18)0.44481 (16)0.04488 (9)0.0598 (8)
H100.67850.42870.04210.072*
C110.7567 (2)0.44776 (17)0.07810 (9)0.0631 (9)
H110.72580.43320.09780.076*
C120.8305 (2)0.47214 (18)0.08231 (8)0.0617 (9)
H120.84910.47410.10500.074*
C130.87821 (17)0.49400 (17)0.05344 (7)0.0538 (7)
H130.92830.51050.05620.065*
C140.8939 (2)0.39585 (17)0.02282 (9)0.0651 (9)
H14A0.84590.36440.03360.078*
H14B0.88900.38740.00260.078*
C150.9149 (2)0.30032 (18)0.04022 (9)0.0744 (10)
H15A0.94950.29110.05270.112*
H15B0.90540.27760.01720.112*
H15C0.86950.27990.05340.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0529 (16)0.0402 (14)0.0461 (15)0.0241 (13)0.0090 (12)0.0049 (12)
Cl10.0920 (10)0.0920 (10)0.0494 (11)0.0460 (5)0.0000.000
Cl20.0408 (4)0.0593 (4)0.0460 (4)0.0230 (3)0.0107 (3)0.0075 (3)
Cl30.162 (5)0.081 (3)0.074 (3)0.053 (3)0.008 (3)0.008 (2)
Cl3A0.121 (5)0.121 (5)0.089 (6)0.053 (5)0.013 (4)0.013 (4)
Cr10.0317 (2)0.0317 (2)0.0285 (3)0.0137 (2)0.00026 (11)0.00026 (11)
N10.0433 (12)0.0364 (11)0.0357 (11)0.0195 (10)0.0063 (9)0.0019 (9)
O10.0815 (15)0.0456 (12)0.0795 (15)0.0364 (11)0.0167 (12)0.0035 (10)
C20.0354 (13)0.0355 (13)0.0348 (13)0.0153 (11)0.0035 (10)0.0025 (10)
N20.0570 (14)0.0368 (12)0.0464 (13)0.0235 (11)0.0147 (11)0.0052 (10)
C30.0333 (13)0.0402 (14)0.0353 (13)0.0170 (11)0.0017 (10)0.0000 (11)
N30.0444 (12)0.0385 (12)0.0380 (12)0.0195 (10)0.0119 (9)0.0077 (9)
C40.0507 (16)0.0506 (16)0.0436 (15)0.0250 (13)0.0131 (12)0.0004 (12)
N40.0347 (10)0.0347 (11)0.0320 (11)0.0156 (9)0.0018 (8)0.0025 (8)
C50.0549 (17)0.0564 (18)0.0526 (17)0.0309 (15)0.0099 (14)0.0084 (14)
C60.0580 (17)0.0441 (15)0.0540 (18)0.0293 (14)0.0019 (14)0.0102 (13)
C70.0449 (14)0.0373 (14)0.0443 (15)0.0206 (12)0.0012 (12)0.0021 (11)
C80.0453 (15)0.0389 (14)0.0414 (15)0.0222 (12)0.0119 (12)0.0096 (11)
C90.0483 (16)0.0450 (16)0.0565 (18)0.0184 (13)0.0061 (13)0.0083 (13)
C100.0513 (17)0.0476 (17)0.077 (2)0.0219 (14)0.0214 (16)0.0115 (15)
C110.076 (2)0.0477 (17)0.072 (2)0.0359 (17)0.0394 (18)0.0169 (15)
C120.096 (3)0.066 (2)0.0365 (16)0.0504 (19)0.0136 (16)0.0093 (13)
C130.0610 (18)0.0626 (19)0.0467 (17)0.0375 (16)0.0064 (14)0.0079 (14)
C140.079 (2)0.0469 (17)0.074 (2)0.0345 (17)0.0306 (18)0.0187 (15)
C150.117 (3)0.058 (2)0.056 (2)0.049 (2)0.001 (2)0.0027 (15)
Geometric parameters (Å, º) top
C1—N21.328 (3)C5—C61.363 (4)
C1—N31.368 (3)C5—H50.9300
C1—C141.489 (4)C6—C71.386 (4)
Cl2—Cr12.2747 (7)C6—H60.9300
Cl3—Cl3i2.028 (19)C7—H70.9300
Cr1—N1i2.040 (2)C8—C91.371 (4)
Cr1—N12.040 (2)C8—C131.378 (4)
Cr1—N4i2.0948 (19)C9—C101.374 (4)
Cr1—N42.0949 (19)C9—H90.9300
Cr1—Cl2i2.2746 (7)C10—C111.370 (4)
N1—C21.315 (3)C10—H100.9300
N1—N21.367 (3)C11—C121.369 (5)
O1—C141.387 (4)C11—H110.9300
O1—C151.425 (4)C12—C131.387 (4)
C2—N31.355 (3)C12—H120.9300
C2—C31.456 (3)C13—H130.9300
C3—N41.353 (3)C14—H14A0.9700
C3—C41.384 (3)C14—H14B0.9700
N3—C81.452 (3)C15—H15A0.9600
C4—C51.379 (4)C15—H15B0.9600
C4—H40.9300C15—H15C0.9600
N4—C71.340 (3)
N2—C1—N3110.5 (2)C6—C5—H5120.3
N2—C1—C14126.8 (2)C4—C5—H5120.3
N3—C1—C14122.7 (2)C5—C6—C7119.3 (3)
N1i—Cr1—N187.33 (12)C5—C6—H6120.4
N1i—Cr1—N4i78.06 (8)C7—C6—H6120.4
N1—Cr1—N4i93.14 (8)N4—C7—C6122.1 (2)
N1i—Cr1—N493.15 (8)N4—C7—H7118.9
N1—Cr1—N478.06 (8)C6—C7—H7118.9
N4i—Cr1—N4167.94 (10)C9—C8—C13122.6 (3)
N1i—Cr1—Cl2i90.84 (6)C9—C8—N3118.4 (2)
N1—Cr1—Cl2i172.01 (6)C13—C8—N3119.0 (2)
N4i—Cr1—Cl2i94.08 (5)C8—C9—C10119.0 (3)
N4—Cr1—Cl2i94.29 (6)C8—C9—H9120.5
N1i—Cr1—Cl2172.01 (6)C10—C9—H9120.5
N1—Cr1—Cl290.83 (6)C11—C10—C9120.1 (3)
N4i—Cr1—Cl294.29 (6)C11—C10—H10120.0
N4—Cr1—Cl294.07 (5)C9—C10—H10120.0
Cl2i—Cr1—Cl292.02 (4)C12—C11—C10120.1 (3)
C2—N1—N2110.0 (2)C12—C11—H11120.0
C2—N1—Cr1114.91 (16)C10—C11—H11120.0
N2—N1—Cr1135.02 (15)C11—C12—C13121.4 (3)
C14—O1—C15112.6 (3)C11—C12—H12119.3
N1—C2—N3108.6 (2)C13—C12—H12119.3
N1—C2—C3119.3 (2)C8—C13—C12116.9 (3)
N3—C2—C3132.1 (2)C8—C13—H13121.5
C1—N2—N1105.3 (2)C12—C13—H13121.6
N4—C3—C4121.7 (2)O1—C14—C1110.1 (2)
N4—C3—C2111.8 (2)O1—C14—H14A109.6
C4—C3—C2126.4 (2)C1—C14—H14A109.6
C2—N3—C1105.6 (2)O1—C14—H14B109.6
C2—N3—C8127.0 (2)C1—C14—H14B109.6
C1—N3—C8127.4 (2)H14A—C14—H14B108.2
C5—C4—C3119.0 (3)O1—C15—H15A109.5
C5—C4—H4120.5O1—C15—H15B109.5
C3—C4—H4120.5H15A—C15—H15B109.5
C7—N4—C3118.4 (2)O1—C15—H15C109.5
C7—N4—Cr1125.86 (17)H15A—C15—H15C109.5
C3—N4—Cr1115.74 (15)H15B—C15—H15C109.5
C6—C5—C4119.4 (3)
Symmetry code: (i) y+1/3, x1/3, z+1/6.

Experimental details

Crystal data
Chemical formula[CrCl2(C15H14N4O)2]Cl
Mr690.95
Crystal system, space groupHexagonal, R3c
Temperature (K)296
a, c (Å)20.8852 (12), 37.620 (4)
V3)14211.1 (19)
Z18
Radiation typeMo Kα
µ (mm1)0.66
Crystal size (mm)0.17 × 0.13 × 0.12
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.896, 0.925
No. of measured, independent and
observed [I > 2σ(I)] reflections
32255, 2785, 2243
Rint0.052
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.119, 1.10
No. of reflections2785
No. of parameters213
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—N12.040 (2)Cr1—Cl2i2.2746 (7)
Cr1—N42.0949 (19)
Symmetry code: (i) y+1/3, x1/3, z+1/6.
 

Acknowledgements

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

References

First citationAlagarsamy, V., Rupeshkumar, M., Kavitha, K., Meena, S., Shankar, D., Siddiqui, A. A. & Rajesh, R. (2008). Eur. J. Med. Chem. 43, 2331–2337.  Web of Science CrossRef PubMed CAS Google Scholar
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