Triaquabis­[bis­(3,5-dimethyl-1,2,4-triazol-1-yl)­methane-κN4]copper(II) bis­(perchlorate)

Xiang, Q.; Cheng, Y.; Ling, Y.; Zhang, L.; Shi, L.-Y.

doi:10.1107/S1600536806048318

Triaquabis[bis(3,5-dimethyl-1,2,4-triazol-1-yl)methane-κN⁴]copper(II) bis(perchlorate)

Q. Xiang, Y. Cheng, Y. Ling, L. Zhang and L.-Y. Shi

The title compound, [Cu(bdtm)₂(H₂O)₃](ClO₄)₂ [bdtm is bis(3,5-dimethyl-1,2,4-triazol-1-yl)methane, C₉H₁₄N₆], is the first example of a mononuclear copper complex with monodentate bdtm ligands. In the cation, which possesses crystallographically imposed twofold rotation symmetry, the Cu^II atom is coordinated by the two N atoms [Cu—N = 2.009 (3) Å] from two symmetry-equivalent bdtm ligands and three O atoms [Cu—O = 1.949 (3) and 2.232 (6) Å] from the water molecules in a distorted trigonal–bipyramidal geometry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048318/cv2135sup1.cif Contains datablocks I, 51028b
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048318/cv2135Isup2.hkl Contains datablock I

CCDC reference: 629637

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
Disorder in solvent or counterion
R factor = 0.042
wR factor = 0.119
Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT221_ALERT_4_B Large Solvent/Anion  O     Ueq(max)/Ueq(min) ...       4.41 Ratio

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for         O3
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        O4'
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for         O5
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        O6'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        O3'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        O5'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         O6
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      44.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........         O6
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O6'
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT432_ALERT_2_C Short Inter X...Y Contact  O6'    ..  C5      ..       2.96 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.40 Deg.
              O3   -CL1  -O3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.30 Deg.
              O5   -CL1  -O5'     1.555   1.555   1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.03

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _reflns_number_total               2815
           Count of symmetry unique reflns         1737
           Completeness (_total/calc)            162.06%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1078
           Fraction of Friedel pairs measured     0.621
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
  12 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Triaqua-bis[bis(3,5-dimethyl-1,2,4-triazol-1-yl)methane]- copper(II) bis(perchlorate) top

Crystal data top

[Cu(C₉H₁₄N₆)₂(H₂O)₃]²⁺·2ClO⁴⁻	D_x = 1.522 Mg m⁻³
M_r = 729.01	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 4719 reflections
Hall symbol: P_4abw_2nw	θ = 2.3–22.6°
a = 9.2157 (3) Å	µ = 0.93 mm⁻¹
c = 37.458 (3) Å	T = 293 K
V = 3181.2 (3) Å³	Block, blue
Z = 4	0.20 × 0.14 × 0.12 mm
F(000) = 1508

Data collection top

Bruker APEXII CCD area-detector diffractometer	2815 independent reflections
Radiation source: fine-focus sealed tube	2581 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→9
T_min = 0.855, T_max = 0.899	k = −10→10
17426 measured reflections	l = −38→44

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0631P)² + 2.3565P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2815 reflections	Δρ_max = 0.53 e Å⁻³
252 parameters	Δρ_min = −0.35 e Å⁻³
24 restraints	Absolute structure: Flack (1983), 1078 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (3)

Special details top

Experimental. CHN analysis, found: C 29.57, H 4.67, N 23.14%, calculated (C₁₈H₃₄Cl₂CuN₁₂O₁₁): C 29.63, H 4.66, N 23.04%.

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)
Cu1	1.01471 (5)	0.01471 (5)	0.0000	0.0418 (2)
O1	1.0943 (4)	−0.0631 (4)	0.04426 (7)	0.0678 (10)
O2	0.8435 (4)	−0.1565 (4)	0.0000	0.102 (2)
N1	0.9259 (3)	0.1827 (3)	0.02630 (7)	0.0417 (7)
N2	0.7856 (4)	0.3481 (4)	0.04636 (8)	0.0444 (7)
N3	0.9200 (4)	0.3872 (4)	0.05805 (9)	0.0544 (9)
N4	0.5943 (4)	0.3969 (4)	0.08796 (8)	0.0472 (7)
N5	0.5058 (4)	0.2790 (4)	0.08809 (8)	0.0528 (8)
N6	0.5248 (4)	0.3735 (4)	0.14299 (8)	0.0559 (9)
C1	1.1626 (6)	0.2832 (7)	0.05099 (16)	0.0870 (18)
H1A	1.2103	0.3106	0.0292	0.131*
H1B	1.1931	0.1875	0.0578	0.131*
H1C	1.1876	0.3508	0.0695	0.131*
C2	1.0026 (5)	0.2843 (5)	0.04546 (10)	0.0510 (9)
C3	0.7891 (4)	0.2276 (4)	0.02692 (8)	0.0393 (8)
C4	0.6615 (4)	0.1607 (5)	0.01008 (11)	0.0555 (11)
H4A	0.6032	0.1145	0.0280	0.083*
H4B	0.6927	0.0898	−0.0071	0.083*
H4C	0.6053	0.2342	−0.0017	0.083*
C5	0.6638 (5)	0.4429 (4)	0.05528 (10)	0.0494 (9)
H5A	0.6983	0.5417	0.0580	0.059*
H5B	0.5937	0.4414	0.0360	0.059*
C6	0.3718 (6)	0.1504 (7)	0.13545 (14)	0.0790 (15)
H6A	0.3624	0.0760	0.1177	0.118*
H6B	0.2778	0.1896	0.1409	0.118*
H6C	0.4136	0.1099	0.1567	0.118*
C7	0.4676 (5)	0.2683 (5)	0.12163 (11)	0.0544 (10)
C8	0.6064 (4)	0.4534 (5)	0.12109 (10)	0.0501 (10)
C9	0.6976 (6)	0.5776 (6)	0.13108 (12)	0.0727 (14)
H9A	0.6394	0.6639	0.1319	0.109*
H9B	0.7734	0.5896	0.1137	0.109*
H9C	0.7397	0.5606	0.1541	0.109*
Cl1	0.48718 (12)	0.80598 (13)	0.05379 (4)	0.0697 (3)
O3	0.6024 (8)	0.8427 (10)	0.0781 (2)	0.208 (10)	0.50
O4	0.5443 (10)	0.7964 (9)	0.01805 (11)	0.158 (6)	0.50
O5	0.3768 (6)	0.9162 (6)	0.0550 (3)	0.115 (5)	0.50
O6	0.4256 (7)	0.6683 (4)	0.0637 (2)	0.121 (5)	0.50
O3'	0.6375 (3)	0.8473 (8)	0.0557 (2)	0.087 (3)	0.50
O4'	0.4358 (7)	0.7706 (11)	0.08906 (12)	0.200 (8)	0.50
O5'	0.4033 (6)	0.9244 (6)	0.03967 (19)	0.063 (2)	0.50
O6'	0.4720 (10)	0.6814 (6)	0.0310 (2)	0.278 (15)	0.50
H1A'	1.046 (4)	−0.096 (5)	0.0619 (8)	0.079 (17)*
H1B'	1.186 (5)	−0.070 (6)	0.0452 (12)	0.088 (19)*
H2A	0.794 (7)	−0.149 (10)	0.0191 (11)	0.15 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0481 (3)	0.0481 (3)	0.0291 (3)	0.0142 (3)	0.00304 (15)	−0.00304 (15)
O1	0.063 (2)	0.105 (3)	0.0350 (14)	0.0375 (19)	0.0123 (13)	0.0182 (15)
O2	0.072 (2)	0.072 (2)	0.162 (7)	−0.015 (3)	0.033 (3)	−0.033 (3)
N1	0.0466 (17)	0.0500 (18)	0.0285 (13)	0.0092 (14)	−0.0004 (13)	−0.0063 (13)
N2	0.0516 (19)	0.0464 (18)	0.0352 (15)	0.0112 (14)	0.0029 (14)	−0.0060 (14)
N3	0.052 (2)	0.061 (2)	0.0494 (19)	0.0041 (17)	−0.0034 (16)	−0.0185 (17)
N4	0.0491 (19)	0.0503 (19)	0.0423 (16)	0.0072 (14)	0.0095 (14)	−0.0048 (14)
N5	0.052 (2)	0.063 (2)	0.0431 (17)	0.0041 (18)	0.0032 (15)	−0.0121 (15)
N6	0.055 (2)	0.074 (2)	0.0386 (16)	−0.0008 (18)	0.0053 (16)	−0.0067 (16)
C1	0.057 (3)	0.103 (4)	0.102 (4)	0.010 (3)	−0.020 (3)	−0.037 (4)
C2	0.050 (2)	0.059 (2)	0.044 (2)	0.010 (2)	−0.0023 (18)	−0.0118 (17)
C3	0.041 (2)	0.048 (2)	0.0283 (15)	0.0085 (15)	0.0038 (14)	−0.0007 (15)
C4	0.046 (2)	0.061 (2)	0.059 (3)	0.0053 (19)	0.0017 (18)	−0.013 (2)
C5	0.060 (2)	0.048 (2)	0.0407 (18)	0.0185 (18)	0.0119 (18)	−0.0003 (17)
C6	0.078 (3)	0.094 (4)	0.064 (3)	−0.015 (3)	0.018 (3)	0.001 (3)
C7	0.047 (2)	0.066 (3)	0.050 (2)	0.004 (2)	0.0097 (19)	−0.0035 (19)
C8	0.048 (2)	0.063 (3)	0.0391 (19)	0.0097 (19)	0.0039 (16)	−0.0099 (17)
C9	0.096 (4)	0.076 (3)	0.046 (2)	−0.017 (3)	0.003 (2)	−0.009 (2)
Cl1	0.0510 (6)	0.0713 (7)	0.0868 (8)	0.0075 (6)	−0.0081 (6)	0.0023 (6)
O3	0.28 (2)	0.120 (11)	0.223 (18)	−0.017 (12)	−0.174 (17)	0.033 (12)
O4	0.181 (12)	0.184 (13)	0.109 (7)	−0.050 (10)	0.072 (8)	−0.055 (8)
O5	0.089 (7)	0.087 (7)	0.169 (12)	0.023 (6)	0.025 (7)	0.011 (7)
O6	0.060 (5)	0.056 (5)	0.246 (15)	0.005 (4)	0.033 (7)	−0.024 (6)
O3'	0.025 (3)	0.142 (8)	0.094 (6)	0.000 (4)	−0.019 (3)	0.023 (6)
O4'	0.113 (9)	0.261 (18)	0.226 (16)	0.005 (11)	0.015 (10)	0.170 (15)
O5'	0.037 (3)	0.073 (5)	0.078 (5)	0.013 (3)	0.005 (4)	0.010 (4)
O6'	0.26 (2)	0.195 (17)	0.38 (3)	0.159 (16)	−0.22 (2)	−0.214 (19)

Geometric parameters (Å, º) top

Cu1—O1ⁱ	1.949 (3)	C4—H4C	0.9600
Cu1—O1	1.949 (3)	C5—H5A	0.9700
Cu1—N1ⁱ	2.009 (3)	C5—H5B	0.9700
Cu1—N1	2.009 (3)	C6—C7	1.492 (7)
Cu1—O2	2.232 (6)	C6—H6A	0.9600
O1—H1A'	0.85 (3)	C6—H6B	0.9600
O1—H1B'	0.85 (4)	C6—H6C	0.9600
O2—H2A	0.85 (5)	C8—C9	1.469 (6)
N1—C3	1.328 (4)	C9—H9A	0.9600
N1—C2	1.375 (5)	C9—H9B	0.9600
N2—C3	1.328 (5)	C9—H9C	0.9600
N2—N3	1.362 (5)	Cl1—O5	1.4382 (9)
N2—C5	1.461 (5)	Cl1—O3	1.4382 (9)
N3—C2	1.304 (5)	Cl1—O6'	1.4383 (9)
N4—C8	1.350 (5)	Cl1—O3'	1.4384 (9)
N4—N5	1.358 (5)	Cl1—O5'	1.4385 (9)
N4—C5	1.445 (5)	Cl1—O6	1.4385 (9)
N5—C7	1.308 (5)	Cl1—O4'	1.4407 (9)
N6—C8	1.334 (5)	Cl1—O4	1.4414 (9)
N6—C7	1.363 (6)	O3—O3'	0.899 (10)
C1—C2	1.489 (7)	O3—O4'	1.723 (8)
C1—H1A	0.9600	O4—O6'	1.343 (9)
C1—H1B	0.9600	O4—O3'	1.717 (9)
C1—H1C	0.9600	O5—O5'	0.630 (10)
C3—C4	1.470 (6)	O6—O6'	1.305 (9)
C4—H4A	0.9600	O6—O4'	1.341 (9)
C4—H4B	0.9600

O1ⁱ—Cu1—O1	179.3 (3)	N6—C7—C6	122.9 (4)
O1ⁱ—Cu1—N1ⁱ	91.12 (12)	N6—C8—N4	107.8 (4)
O1—Cu1—N1ⁱ	88.70 (12)	N6—C8—C9	126.6 (4)
O1ⁱ—Cu1—N1	88.70 (12)	N4—C8—C9	125.6 (4)
O1—Cu1—N1	91.12 (12)	C8—C9—H9A	109.5
N1ⁱ—Cu1—N1	150.25 (19)	C8—C9—H9B	109.5
O1ⁱ—Cu1—O2	90.35 (12)	H9A—C9—H9B	109.5
O1—Cu1—O2	90.35 (12)	C8—C9—H9C	109.5
N1ⁱ—Cu1—O2	104.88 (9)	H9A—C9—H9C	109.5
N1—Cu1—O2	104.88 (9)	H9B—C9—H9C	109.5
Cu1—O1—H1A'	126 (3)	O5—Cl1—O3	109.60 (9)
Cu1—O1—H1B'	116 (3)	O5—Cl1—O6'	120.9 (6)
H1A'—O1—H1B'	117 (4)	O3—Cl1—O6'	129.5 (6)
Cu1—O2—H2A	109 (5)	O5—Cl1—O3'	119.5 (5)
C3—N1—C2	105.5 (3)	O3—Cl1—O3'	36.4 (4)
C3—N1—Cu1	129.5 (3)	O6'—Cl1—O3'	109.57 (9)
C2—N1—Cu1	124.8 (3)	O5—Cl1—O5'	25.3 (4)
C3—N2—N3	112.0 (3)	O3—Cl1—O5'	116.8 (6)
C3—N2—C5	130.1 (4)	O6'—Cl1—O5'	109.56 (9)
N3—N2—C5	117.9 (3)	O3'—Cl1—O5'	109.58 (9)
C2—N3—N2	102.8 (3)	O5—Cl1—O6	109.59 (9)
C8—N4—N5	110.8 (3)	O3—Cl1—O6	109.58 (9)
C8—N4—C5	129.0 (4)	O6'—Cl1—O6	54.0 (4)
N5—N4—C5	120.2 (3)	O3'—Cl1—O6	126.9 (5)
C7—N5—N4	103.0 (3)	O5'—Cl1—O6	123.5 (5)
C8—N6—C7	104.4 (3)	O5—Cl1—O4'	84.1 (4)
C2—C1—H1A	109.5	O3—Cl1—O4'	73.5 (4)
C2—C1—H1B	109.5	O6'—Cl1—O4'	109.42 (9)
H1A—C1—H1B	109.5	O3'—Cl1—O4'	109.30 (9)
C2—C1—H1C	109.5	O5'—Cl1—O4'	109.40 (9)
H1A—C1—H1C	109.5	O6—Cl1—O4'	55.5 (4)
H1B—C1—H1C	109.5	O5—Cl1—O4	109.38 (9)
N3—C2—N1	112.6 (4)	O3—Cl1—O4	109.37 (9)
N3—C2—C1	122.2 (4)	O6'—Cl1—O4	55.6 (4)
N1—C2—C1	125.2 (4)	O3'—Cl1—O4	73.2 (4)
N1—C3—N2	107.1 (3)	O5'—Cl1—O4	84.3 (4)
N1—C3—C4	128.4 (3)	O6—Cl1—O4	109.31 (9)
N2—C3—C4	124.5 (3)	O4'—Cl1—O4	163.3 (4)
C3—C4—H4A	109.5	O3'—O3—Cl1	71.8 (2)
C3—C4—H4B	109.5	O3'—O3—O4'	124.2 (3)
H4A—C4—H4B	109.5	Cl1—O3—O4'	53.3 (2)
C3—C4—H4C	109.5	O6'—O4—Cl1	62.1 (2)
H4A—C4—H4C	109.5	O6'—O4—O3'	99.7 (4)
H4B—C4—H4C	109.5	Cl1—O4—O3'	53.3 (2)
N4—C5—N2	111.0 (3)	O5'—O5—Cl1	77.4 (2)
N4—C5—H5A	109.4	O6'—O6—O4'	125.30 (11)
N2—C5—H5A	109.4	O6'—O6—Cl1	63.0 (2)
N4—C5—H5B	109.4	O4'—O6—Cl1	62.3 (2)
N2—C5—H5B	109.4	O3—O3'—Cl1	71.8 (2)
H5A—C5—H5B	108.0	O3—O3'—O4	124.95 (17)
C7—C6—H6A	109.5	Cl1—O3'—O4	53.5 (2)
C7—C6—H6B	109.5	O6—O4'—Cl1	62.2 (2)
H6A—C6—H6B	109.5	O6—O4'—O3	99.5 (4)
C7—C6—H6C	109.5	Cl1—O4'—O3	53.2 (2)
H6A—C6—H6C	109.5	O5—O5'—Cl1	77.3 (2)
H6B—C6—H6C	109.5	O6—O6'—O4	125.05 (16)
N5—C7—N6	114.0 (4)	O6—O6'—Cl1	63.0 (2)
N5—C7—C6	123.2 (4)	O4—O6'—Cl1	62.3 (2)

O1ⁱ—Cu1—N1—C3	55.5 (3)	O3—Cl1—O6—O6'	−125.1 (7)
O1—Cu1—N1—C3	−125.2 (3)	O3'—Cl1—O6—O6'	−88.4 (5)
N1ⁱ—Cu1—N1—C3	145.4 (3)	O5'—Cl1—O6—O6'	90.8 (4)
O2—Cu1—N1—C3	−34.6 (3)	O4'—Cl1—O6—O6'	−177.6 (7)
O1ⁱ—Cu1—N1—C2	−118.3 (3)	O4—Cl1—O6—O6'	−5.3 (7)
O1—Cu1—N1—C2	61.0 (3)	O5—Cl1—O6—O4'	−67.9 (5)
N1ⁱ—Cu1—N1—C2	−28.3 (3)	O3—Cl1—O6—O4'	52.4 (5)
O2—Cu1—N1—C2	151.7 (3)	O6'—Cl1—O6—O4'	177.6 (7)
C3—N2—N3—C2	−1.2 (4)	O3'—Cl1—O6—O4'	89.2 (4)
C5—N2—N3—C2	−178.9 (3)	O5'—Cl1—O6—O4'	−91.6 (5)
C8—N4—N5—C7	−0.2 (4)	O4—Cl1—O6—O4'	172.3 (5)
C5—N4—N5—C7	178.1 (3)	O4'—O3—O3'—Cl1	10.5 (9)
N2—N3—C2—N1	0.2 (4)	Cl1—O3—O3'—O4	−6.2 (8)
N2—N3—C2—C1	178.6 (5)	O4'—O3—O3'—O4	4.2 (17)
C3—N1—C2—N3	0.8 (4)	O5—Cl1—O3'—O3	83.2 (7)
Cu1—N1—C2—N3	175.9 (3)	O6'—Cl1—O3'—O3	−130.9 (10)
C3—N1—C2—C1	−177.5 (5)	O5'—Cl1—O3'—O3	108.9 (10)
Cu1—N1—C2—C1	−2.5 (6)	O6—Cl1—O3'—O3	−71.8 (9)
C2—N1—C3—N2	−1.5 (4)	O4'—Cl1—O3'—O3	−11.0 (10)
Cu1—N1—C3—N2	−176.2 (2)	O4—Cl1—O3'—O3	−173.6 (9)
C2—N1—C3—C4	178.9 (4)	O5—Cl1—O3'—O4	−103.1 (3)
Cu1—N1—C3—C4	4.2 (6)	O3—Cl1—O3'—O4	173.6 (9)
N3—N2—C3—N1	1.8 (4)	O6'—Cl1—O3'—O4	42.8 (5)
C5—N2—C3—N1	179.1 (3)	O5'—Cl1—O3'—O4	−77.5 (4)
N3—N2—C3—C4	−178.7 (4)	O6—Cl1—O3'—O4	101.8 (3)
C5—N2—C3—C4	−1.3 (6)	O4'—Cl1—O3'—O4	162.7 (4)
C8—N4—C5—N2	102.1 (4)	O6'—O4—O3'—O3	−36.7 (10)
N5—N4—C5—N2	−75.9 (5)	Cl1—O4—O3'—O3	7.4 (10)
C3—N2—C5—N4	89.9 (5)	O6'—O4—O3'—Cl1	−44.0 (3)
N3—N2—C5—N4	−92.8 (4)	O6'—O6—O4'—Cl1	2.7 (8)
N4—N5—C7—N6	0.9 (5)	O6'—O6—O4'—O3	−36.5 (8)
N4—N5—C7—C6	−178.3 (4)	Cl1—O6—O4'—O3	−39.19 (17)
C8—N6—C7—N5	−1.2 (5)	O5—Cl1—O4'—O6	118.7 (3)
C8—N6—C7—C6	178.0 (4)	O3—Cl1—O4'—O6	−128.9 (4)
C7—N6—C8—N4	1.0 (4)	O6'—Cl1—O4'—O6	−2.1 (6)
C7—N6—C8—C9	−177.0 (5)	O3'—Cl1—O4'—O6	−122.1 (6)
N5—N4—C8—N6	−0.5 (4)	O5'—Cl1—O4'—O6	117.9 (6)
C5—N4—C8—N6	−178.7 (3)	O4—Cl1—O4'—O6	−26.3 (16)
N5—N4—C8—C9	177.5 (4)	O5—Cl1—O4'—O3	−112.47 (17)
C5—N4—C8—C9	−0.6 (7)	O6'—Cl1—O4'—O3	126.8 (6)
O5—Cl1—O3—O3'	−113.5 (9)	O3'—Cl1—O4'—O3	6.8 (6)
O6'—Cl1—O3—O3'	67.3 (10)	O5'—Cl1—O4'—O3	−113.2 (6)
O5'—Cl1—O3—O3'	−87.0 (9)	O6—Cl1—O4'—O3	128.9 (4)
O6—Cl1—O3—O3'	126.3 (9)	O4—Cl1—O4'—O3	102.6 (14)
O4'—Cl1—O3—O3'	169.2 (10)	O3'—O3—O4'—O6	31.8 (12)
O4—Cl1—O3—O3'	6.4 (9)	Cl1—O3—O4'—O6	44.3 (3)
O5—Cl1—O3—O4'	77.4 (4)	O3'—O3—O4'—Cl1	−12.4 (11)
O6'—Cl1—O3—O4'	−101.9 (4)	O3—Cl1—O5'—O5	−79.1 (12)
O3'—Cl1—O3—O4'	−169.2 (10)	O6'—Cl1—O5'—O5	121.7 (14)
O5'—Cl1—O3—O4'	103.8 (2)	O3'—Cl1—O5'—O5	−118.1 (14)
O6—Cl1—O3—O4'	−42.9 (4)	O6—Cl1—O5'—O5	62.6 (15)
O4—Cl1—O3—O4'	−162.7 (4)	O4'—Cl1—O5'—O5	1.7 (14)
O5—Cl1—O4—O6'	−114.8 (7)	O4—Cl1—O5'—O5	172.0 (13)
O3—Cl1—O4—O6'	125.2 (7)	O4'—O6—O6'—O4	3.9 (16)
O3'—Cl1—O4—O6'	129.2 (4)	Cl1—O6—O6'—O4	6.6 (9)
O5'—Cl1—O4—O6'	−118.4 (3)	O4'—O6—O6'—Cl1	−2.6 (8)
O6—Cl1—O4—O6'	5.2 (7)	Cl1—O4—O6'—O6	−6.6 (9)
O4'—Cl1—O4—O6'	27.9 (18)	O3'—O4—O6'—O6	32.5 (10)
O5—Cl1—O4—O3'	116.0 (5)	O3'—O4—O6'—Cl1	39.12 (18)
O3—Cl1—O4—O3'	−4.0 (5)	O5—Cl1—O6'—O6	−92.7 (5)
O6'—Cl1—O4—O3'	−129.2 (4)	O3—Cl1—O6'—O6	86.4 (6)
O5'—Cl1—O4—O3'	112.44 (17)	O3'—Cl1—O6'—O6	122.0 (6)
O6—Cl1—O4—O3'	−124.0 (5)	O5'—Cl1—O6'—O6	−117.8 (6)
O4'—Cl1—O4—O3'	−101.2 (15)	O4'—Cl1—O6'—O6	2.1 (6)
O3—Cl1—O5—O5'	111.5 (13)	O4—Cl1—O6'—O6	173.9 (8)
O6'—Cl1—O5—O5'	−69.2 (13)	O5—Cl1—O6'—O4	93.3 (5)
O3'—Cl1—O5—O5'	72.7 (14)	O3—Cl1—O6'—O4	−87.5 (6)
O6—Cl1—O5—O5'	−128.2 (13)	O3'—Cl1—O6'—O4	−52.0 (6)
O4'—Cl1—O5—O5'	−178.4 (13)	O5'—Cl1—O6'—O4	68.3 (6)
O4—Cl1—O5—O5'	−8.4 (13)	O6—Cl1—O6'—O4	−173.9 (8)
O5—Cl1—O6—O6'	114.6 (7)	O4'—Cl1—O6'—O4	−171.8 (6)

Symmetry code: (i) y+1, x−1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A′···N6ⁱⁱ	0.85 (3)	1.83 (3)	2.659 (4)	163 (4)
O1—H1B′···O5ⁱⁱⁱ	0.85 (4)	1.80 (3)	2.641 (7)	171 (5)
O1—H1B′···O5′ⁱⁱⁱ	0.85 (4)	2.01 (3)	2.855 (7)	171 (4)
O2—H2A···O3′^iv	0.85 (5)	1.99 (6)	2.821 (6)	165 (7)
O2—H2A···O4^iv	0.85 (5)	2.36 (7)	2.872 (10)	120 (5)
C4—H4A···O5′^iv	0.96	2.58	3.411 (7)	145
C4—H4C···O6′^v	0.96	2.55	3.261 (10)	131
C6—H6B···O4′^vi	0.96	2.24	3.190 (9)	172
C6—H6B···O6^vi	0.96	2.54	3.342 (9)	141

Symmetry codes: (ii) −x+3/2, y−1/2, −z+1/4; (iii) x+1, y−1, z; (iv) x, y−1, z; (v) y, x, −z; (vi) −x+1/2, y−1/2, −z+1/4.

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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

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Triaquabis­[bis­(3,5-dimethyl-1,2,4-triazol-1-yl)­methane-κN4]copper(II) bis­(perchlorate)

Supporting information

Key indicators

checkCIF/PLATON results

Triaquabis[bis(3,5-dimethyl-1,2,4-triazol-1-yl)methane-κN⁴]copper(II) bis(perchlorate)