Dichloridobis[3-meth-oxy-methyl-4-phenyl-5-(2-pyrid-yl)-4H-1,2,4-triazole-κN,N]chromium(III) chloride.

In the title complex, [CrCl(2)(C(15)H(14)N(4)O)(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 octa-hedral CrN(2)N'(2)Cl(2) geometry. One of the two independent Cl(-) counter-anions sits on a special position (site symmetry [Formula: see text].) 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 = 690.95

Hexagonal,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 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

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039328/wm2515sup1.cif

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

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

[CrCl2(C15H14N4O)2]Cl	Dx = 1.453 Mg m−3
Mr = 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

Bruker APEXII CCD diffractometer	2785 independent reflections
Radiation source: fine-focus sealed tube	2243 reflections with I > 2σ(I)
graphite	Rint = 0.052
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −24→24
Tmin = 0.896, Tmax = 0.925	k = −24→24
32255 measured reflections	l = −44→42

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(Fo2) + (0.072P)2 + 5.702P] where P = (Fo2 + 2Fc2)/3
2785 reflections	(Δ/σ)max = 0.002
213 parameters	Δρmax = 0.68 e Å−3
18 restraints	Δρmin = −0.31 e Å−3

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	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*

	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)

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)

Table 1

Selected bond lengths (Å)

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

Symmetry code: (i) .