Bis(3,5-di­methyl-1,2,4-triazolato-κN⁴)bis­(pivalic acid-κO)copper(II) dihydrate

The mol­ecule of the title complex, [Cu(C₄H₆N₃)₂(C₅H₁₀O₂)₂]·2H₂O, is situated about a site of symmetry 2/m and shows a trans-N₂O₂ square-planar coordination geometry for the Cu^II centre. The crystal structure exhibits a two-dimensional layer arrangement mediated by intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.062
• wR factor = 0.164
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C3      ..       5.92 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O1      ..       5.04 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        Cu1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(3,5-dimethyl-1,2,4-triazolato-κN⁴)bis(pivalic acid-κO)copper(II) dihydrate

Crystal data

[Cu(C4H6N3)2(C5H10O2)2]·2H2O	F(000) = 526
Mr = 496.07	Dx = 1.222 Mg m^−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 709 reflections
a = 13.270 (3) Å	θ = 2.9–22.9°
b = 12.861 (3) Å	µ = 0.85 mm^−1
c = 8.770 (2) Å	T = 293 K
β = 115.791 (4)°	Block, red
V = 1347.6 (5) Å^3	0.33 × 0.28 × 0.23 mm
Z = 2

Data collection

Bruker SMART Apex CCD area detector diffractometer	1311 independent reflections
Radiation source: sealed tube	1141 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→15
Tmin = 0.767, Tmax = 0.829	k = −15→15
3525 measured reflections	l = −10→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.09P)^2 + 1.95P] where P = (Fo^2 + 2Fc^2)/3
1311 reflections	(Δ/σ)max < 0.001
84 parameters	Δρmax = 0.38 e Å^−3
3 restraints	Δρmin = −0.50 e Å^−3

Special details

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

13.2662 (0.0031) x - 0.0000 (0.0001) y - 4.0044 (0.0172) z = 2.6286 (0.0175)

* 0.0000 (0.0000) Cu1 * 0.0000 (0.0000) O2 * 0.0000 (0.0000) O2_$1 * 0.0000 (0.0000) N1 * 0.0000 (0.0000) N1_$1

Rms deviation of fitted atoms = 0.0000

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.0000	1.0000	0.0312 (3)
C1	0.3898 (4)	0.1839 (4)	1.1669 (6)	0.0540 (12)
H1D	0.3643	0.2436	1.2059	0.081*
H1E	0.4382	0.1430	1.2623	0.081*
H1F	0.3266	0.1427	1.0949	0.081*
C2	0.4522 (4)	0.2185 (4)	1.0702 (6)	0.0467 (10)
C3	0.3227 (6)	0.0000	0.7173 (6)	0.0542 (17)
C4	0.2394 (4)	0.0000	0.5375 (6)	0.0540 (17)
C5	0.1606 (4)	0.0904 (4)	0.4994 (7)	0.0623 (14)
H5A	0.1247	0.0885	0.5737	0.093*
H5B	0.1050	0.0862	0.3840	0.093*
H5C	0.2017	0.1541	0.5162	0.093*
C6	0.2913 (6)	0.0000	0.4155 (9)	0.0616 (19)
H6A	0.2348	0.0000	0.3005	0.092*
H6B	0.3370	0.0610	0.4353	0.092*
N1	0.5000	0.1551 (4)	1.0000	0.0449 (12)
N2	0.4691 (4)	0.3161 (3)	1.0473 (6)	0.0575 (11)
O1	0.2924 (4)	0.0000	0.8337 (5)	0.0418 (10)
H1B	0.2247	0.0000	0.8191	0.050*
O2	0.4246 (4)	0.0000	0.7501 (5)	0.0468 (11)
O3	0.1184 (5)	0.0000	0.9043 (8)	0.0671 (15)
H3A	0.0793	0.0540	0.8626	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0427 (6)	0.0220 (5)	0.0336 (5)	0.000	0.0211 (4)	0.000
C1	0.058 (3)	0.061 (3)	0.054 (3)	−0.002 (2)	0.036 (2)	−0.003 (2)
C2	0.053 (3)	0.044 (2)	0.052 (2)	0.001 (2)	0.031 (2)	0.005 (2)
C3	0.065 (5)	0.055 (4)	0.047 (4)	0.000	0.028 (3)	0.000
C4	0.052 (4)	0.069 (5)	0.050 (4)	0.000	0.030 (3)	0.000
C5	0.080 (4)	0.052 (3)	0.066 (3)	0.003 (3)	0.041 (3)	0.008 (2)
C6	0.064 (5)	0.064 (5)	0.069 (5)	0.000	0.040 (4)	0.000
N1	0.056 (3)	0.036 (3)	0.052 (3)	0.000	0.033 (3)	0.000
N2	0.066 (3)	0.044 (2)	0.075 (3)	0.0006 (19)	0.043 (2)	−0.003 (2)
O1	0.052 (2)	0.050 (3)	0.042 (2)	0.000	0.038 (2)	0.000
O2	0.057 (3)	0.047 (3)	0.045 (2)	0.000	0.031 (2)	0.000
O3	0.079 (4)	0.052 (3)	0.094 (4)	0.000	0.060 (3)	0.000

Geometric parameters (Å, º)

Cu1—O2	1.974 (4)	C4—C5^ii	1.501 (7)
Cu1—O2^i	1.974 (4)	C4—C5	1.501 (7)
Cu1—N1^i	1.994 (5)	C4—C6	1.503 (10)
Cu1—N1	1.994 (5)	C5—H5A	0.9600
C1—C2	1.488 (6)	C5—H5B	0.9600
C1—H1D	0.9600	C5—H5C	0.9600
C1—H1E	0.9600	C6—H6A	0.9599
C1—H1F	0.9600	C6—H6B	0.9600
C2—N2	1.306 (6)	N1—C2^iii	1.337 (5)
C2—N1	1.337 (5)	N2—N2^iii	1.399 (8)
C3—O1	1.251 (7)	O1—H1B	0.8501
C3—O2	1.253 (8)	O3—H3A	0.8482
C3—C4	1.480 (7)
O2—Cu1—O2^i	180.000 (1)	C5^ii—C4—C5	101.5 (5)
O2—Cu1—N1^i	90.000 (1)	C3—C4—C6	113.4 (5)
O2^i—Cu1—N1^i	90.000 (1)	C5^ii—C4—C6	109.4 (3)
O2—Cu1—N1	90.00 (1)	C5—C4—C6	109.4 (3)
O2^i—Cu1—N1	90.000 (1)	C4—C5—H5A	109.5
N1^i—Cu1—N1	180.000 (1)	C4—C5—H5B	109.5
C2—C1—H1D	109.5	H5A—C5—H5B	109.5
C2—C1—H1E	109.5	C4—C5—H5C	109.5
H1D—C1—H1E	109.5	H5A—C5—H5C	109.5
C2—C1—H1F	109.5	H5B—C5—H5C	109.5
H1D—C1—H1F	109.5	C4—C6—H6A	110.9
H1E—C1—H1F	109.5	C4—C6—H6B	108.7
N2—C2—N1	111.6 (4)	H6A—C6—H6B	109.5
N2—C2—C1	123.4 (4)	C2—N1—C2^iii	104.8 (5)
N1—C2—C1	125.0 (4)	Cu1—N1—C2	127.6 (3)
O1—C3—O2	120.7 (5)	Cu1^iii—N1—C2	127.6 (3)
O1—C3—C4	120.8 (6)	C2—N2—N2^iii	106.0 (3)
O2—C3—C4	118.4 (5)	C3—O1—H1B	124.8
C3—C4—C5^ii	111.2 (4)	Cu1—O2—C3	103.3 (3)
C3—C4—C5	111.2 (4)
O1—C3—C4—C5^ii	−56.2 (3)	O2—Cu1—N1—C2	120.2 (3)
O2—C3—C4—C5^ii	123.8 (3)	O2^i—Cu1—N1—C2	−59.8 (3)
O1—C3—C4—C5	56.2 (3)	O2—Cu1—N1—C2^iii	−59.8 (3)
O2—C3—C4—C5	−123.8 (3)	O2^i—Cu1—N1—C2^iii	120.2 (3)
O1—C3—C4—C6	180.000 (2)	N1—C2—N2—N2^iii	1.1 (7)
O2—C3—C4—C6	0.000 (2)	C1—C2—N2—N2^iii	179.5 (5)
N2—C2—N1—C2^iii	−0.4 (3)	O1—C3—O2—Cu1	0.000 (1)
C1—C2—N1—C2^iii	−178.9 (6)	C4—C3—O2—Cu1	180.000 (1)
N2—C2—N1—Cu1	179.6 (3)	N1^i—Cu1—O2—C3	90.00 (1)
C1—C2—N1—Cu1	1.1 (6)	N1—Cu1—O2—C3	−90.00 (2)

Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, −y, z; (iii) −x+1, y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O3	0.85	1.86	2.637 (6)	151
O3—H3A···N2^iv	0.85	2.07	2.748 (5)	137

Symmetry code: (iv) −x+1/2, −y+1/2, −z+2.