catena-Poly[[bis­[μ-1,4-bis­(1,2,4-triazol-1-ylmeth­yl)benzene-κ²N⁴:N^4′]copper(I)] perchlorate]

The crystal structure of the title compound, {[Cu(C₁₂H₁₂N₆)]ClO₄}_n, consists of a one-dimensional cationic copper(I) chain and uncoordinated ClO₄⁻ anions. In the cationic chain, the Cu^I center, which lies on a crystallographic twofold rotation axis, is coordinated by two N atoms from two 1,4-bis­(1,2,4-triazol-1-ylmeth­yl)benzene ligands, giving a linear coordination geometry, and the 1,4-bis­(1,2,4-triazol-1-ylmeth­yl)­benzene ligand adopts a bis-monodentate bridging mode, linking Cu^I atoms. The anion O atoms are disordered equally over two sites.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.046
• wR factor = 0.107
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C
SHFSU01_ALERT_2_C  The absolute value of parameter shift to su ratio > 0.05
            Absolute value of the parameter shift to su ratio given   0.077
            Additional refinement cycles may be required.
PLAT080_ALERT_2_C Maximum Shift/Error ............................       0.08
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.67
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      24.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O1'
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O3'
PLAT432_ALERT_2_C Short Inter X...Y Contact  C1     ..  O4      ..       2.96 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C2     ..  O3'     ..       2.94 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C3     ..  O3      ..       3.00 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N1  -CU1 -N1  -C1    -41.60  0.30   2.756   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            N1  -CU1 -N1  -C2    127.80  0.30   2.756   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      38.90 Deg.
              O3'  -CL1  -O4      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      38.90 Deg.
              O3'  -CL1  -O4      2.656   1.555   2.656
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      32.00 Deg.
              O1'  -CL1  -O2      2.656   1.555   2.656
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      32.00 Deg.
              O1'  -CL1  -O2      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      34.40 Deg.
              O2   -CL1  -O3      2.656   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      34.40 Deg.
              O2   -CL1  -O3      1.555   1.555   2.656
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.90 Deg.
              O4   -CL1  -O1      2.656   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.90 Deg.
              O4   -CL1  -O1      1.555   1.555   2.656

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        188

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  20 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
  15 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

The crystal structure of (I) comprises a one-dimensional cationic [CuL]_n chain [L is 1,4-bis(1,2,4-triazol-1-ylmethyl)benzene] and uncoordinated [ClO₄] anion. Within the chain, the coordination geometry of each Cu^I atom is linear (Fig.1 and Table 1). The Cu^I atom, which is two-coordinated by two N atoms from two symmetry-related L liagands, with a unique Cu—N distance of 1.867 (3) Å. The N1—Cu1—N1A bond angles is 174.79 (18) °. Each L ligand coordinates to two Cu^I atoms, acting as a bridging ligand, forming an extended cationic chain structure (Fig.2). the distance between the closest Cu^I atoms in the chain is 13.1559 (2) Å and the dihedral angle between the benzene with 1,2,4-triazole plane in one L ligand is 91 (3) °.

The corresponding copper(II) coordination polymer has double-stranded chain structures. (Li et al., 2005).

Related literature

The corresponding copper(II) coordination polymer has a double-stranded chain structure (Li et al., 2005).

S2. Experimental

The ligand L was prepared according to the reported procedure (Li et al., 2005). Copper(II) perchlorate hexahydrate (37.1 mg, 0.10 mmol) and copper plates (12.8 mg, 0.2 mmol) were stirred in acetone (5 cm³) under an ethylene atmosphere for 1 h, and to the resulting colourless solution was added an acetone solution (5 cm³) containing L (48 mg, 0.20 mmol) under argon. The yellow mixture was stirred, and the filtrate transferred to a 10 mm diameter glass tube and layered with n-pentane (2 cm³) as a diffusion solvent. After standing for 2 weeks at 278 K, pale yellow crystal was obtained in 62% Yield. Analysis calculated for C₁₂H₁₂ CuN₆O₄Cl: C 35.74, H 3.00, N 20.84%; found: C 35.63, H 2.94, N 20.78%).

S3. Refinement

The perchlorate O atoms show positional disorder, and they were refined as two groups sharing the same Cl atom. As the occupancy could not be satisfactorily refined, the eight O atoms were each given site occupancy of 0.5. The C—O(1.45 (1) Å) and O —O distances were restrained with approximate equality. The displacement parameters of the disordered O atoms were also restrained weakly to be approximately isotropic. The aromatic [C —H = 0.93 Å and U_iso(H) =1.2U_eq(C)] and methylene H atoms [C—H= 0.96 Å and U_iso(H) =1.5U_eq(C)] were included in the refinement in the riding-model approximation.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures

	Fig. 1. Part of the structure of (I) showing the coordination environment of atom Cu^I. Displacement ellipsoids are shown at the 30% probability level.[symmetry codes: (i) x + 2, y, -z + 3/2}
	Fig. 2. A view of the one-dimensional structure of (I).

catena-Poly[[bis[µ-1,4-bis(1,2,4-triazol-1-ylmethyl)benzene- κ²N⁴:N^4']copper(I)] perchlorate]

Crystal data

[Cu(C12H12N6)]ClO4	F(000) = 816
Mr = 403.28	Dx = 1.719 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 670 reflections
a = 16.098 (6) Å	θ = 3.2–25.2°
b = 11.550 (4) Å	µ = 1.61 mm^−1
c = 10.687 (4) Å	T = 293 K
β = 128.349 (5)°	Block, colorless
V = 1558.4 (10) Å^3	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1595 independent reflections
Radiation source: fine-focus sealed tube	1106 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −20→15
Tmin = 0.684, Tmax = 0.788	k = −11→14
4433 measured reflections	l = −13→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 2.5014P] where P = (Fo^2 + 2Fc^2)/3
1595 reflections	(Δ/σ)max = 0.077
165 parameters	Δρmax = 0.54 e Å^−3
188 restraints	Δρmin = −0.35 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.

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	Occ. (<1)
Cu1	1.0000	0.55003 (7)	0.7500	0.0571 (3)
C1	0.8162 (3)	0.4702 (3)	0.7079 (4)	0.0428 (9)
H1	0.7953	0.4219	0.6234	0.051*
C2	0.8950 (3)	0.5942 (3)	0.8917 (4)	0.0424 (9)
H2	0.9431	0.6509	0.9610	0.051*
C3	0.6806 (3)	0.4100 (4)	0.7408 (5)	0.0500 (11)
H3A	0.6478	0.3664	0.6430	0.060*
H3B	0.6279	0.4623	0.7258	0.060*
C4	0.7177 (3)	0.3277 (3)	0.8767 (4)	0.0386 (9)
C5	0.8028 (3)	0.2532 (3)	0.9363 (5)	0.0435 (10)
H5	0.8388	0.2551	0.8940	0.052*
C6	0.8344 (3)	0.1764 (3)	1.0581 (4)	0.0419 (9)
H6	0.8912	0.1269	1.0965	0.050*
N1	0.8975 (3)	0.5426 (3)	0.7800 (4)	0.0428 (8)
N2	0.8187 (3)	0.5572 (3)	0.8931 (4)	0.0444 (8)
N3	0.7692 (3)	0.4769 (3)	0.7740 (3)	0.0397 (8)
Cl1	0.5000	0.67676 (13)	0.7500	0.0635 (5)
O1	0.4610 (15)	0.7125 (15)	0.840 (2)	0.079 (7)	0.188 (7)
O2	0.5716 (14)	0.5829 (14)	0.838 (2)	0.107 (9)	0.188 (7)
O3	0.4091 (12)	0.6380 (15)	0.5978 (12)	0.088 (7)	0.188 (7)
O4	0.5486 (13)	0.7722 (13)	0.7406 (19)	0.081 (7)	0.188 (7)
O1'	0.5238 (10)	0.5799 (9)	0.8375 (14)	0.090 (5)	0.312 (7)
O2'	0.3811 (6)	0.6946 (11)	0.6356 (13)	0.095 (5)	0.312 (7)
O3'	0.5456 (10)	0.7812 (9)	0.8234 (14)	0.138 (7)	0.312 (7)
O4'	0.5214 (9)	0.6559 (11)	0.6319 (11)	0.076 (4)	0.312 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0644 (6)	0.0653 (6)	0.0645 (5)	0.000	0.0513 (5)	0.000
C1	0.055 (3)	0.042 (2)	0.037 (2)	0.005 (2)	0.032 (2)	0.0051 (17)
C2	0.049 (2)	0.040 (2)	0.040 (2)	0.0024 (18)	0.029 (2)	0.0043 (17)
C3	0.046 (3)	0.060 (3)	0.041 (2)	−0.006 (2)	0.025 (2)	0.0061 (19)
C4	0.039 (2)	0.038 (2)	0.0359 (19)	−0.0073 (17)	0.0221 (18)	−0.0034 (16)
C5	0.048 (2)	0.050 (2)	0.046 (2)	−0.0082 (19)	0.036 (2)	−0.0047 (18)
C6	0.038 (2)	0.041 (2)	0.044 (2)	−0.0012 (17)	0.0241 (19)	−0.0026 (17)
N1	0.050 (2)	0.0454 (18)	0.0406 (17)	0.0073 (17)	0.0319 (16)	0.0091 (15)
N2	0.057 (2)	0.0431 (19)	0.0416 (17)	−0.0015 (17)	0.0351 (17)	−0.0014 (15)
N3	0.051 (2)	0.0395 (18)	0.0338 (16)	0.0006 (15)	0.0288 (16)	0.0054 (13)
Cl1	0.0879 (13)	0.0418 (8)	0.0572 (10)	0.000	0.0432 (10)	0.000
O1	0.086 (10)	0.068 (11)	0.093 (11)	0.016 (8)	0.060 (8)	−0.013 (8)
O2	0.119 (13)	0.097 (12)	0.114 (12)	0.041 (9)	0.076 (9)	0.015 (9)
O3	0.097 (11)	0.095 (10)	0.047 (8)	−0.018 (9)	0.032 (7)	−0.019 (8)
O4	0.091 (10)	0.070 (9)	0.058 (9)	−0.044 (7)	0.034 (7)	−0.001 (7)
O1'	0.080 (8)	0.079 (7)	0.108 (8)	0.011 (6)	0.057 (7)	0.045 (6)
O2'	0.070 (7)	0.108 (9)	0.110 (8)	0.011 (6)	0.057 (6)	0.000 (7)
O3'	0.154 (11)	0.116 (9)	0.141 (10)	−0.042 (8)	0.090 (8)	−0.034 (8)
O4'	0.087 (8)	0.085 (8)	0.057 (6)	0.010 (6)	0.046 (5)	−0.002 (5)

Geometric parameters (Å, º)

Cu1—N1^i	1.868 (3)	Cl1—O3'^iii	1.377 (7)
Cu1—N1	1.868 (3)	Cl1—O4	1.391 (9)
C1—N3	1.318 (5)	Cl1—O4^iii	1.391 (9)
C1—N1	1.325 (5)	Cl1—O2^iii	1.429 (9)
C1—H1	0.9300	Cl1—O2	1.429 (9)
C2—N2	1.309 (5)	Cl1—O3	1.426 (8)
C2—N1	1.358 (5)	Cl1—O3^iii	1.426 (8)
C2—H2	0.9300	Cl1—O1	1.496 (9)
C3—N3	1.459 (5)	Cl1—O1^iii	1.496 (9)
C3—C4	1.515 (5)	O1—O4^iii	1.04 (3)
C3—H3A	0.9700	O2—O3^iii	0.84 (3)
C3—H3B	0.9700	O2—O2^iii	1.86 (3)
C4—C6^ii	1.385 (5)	O3—O2^iii	0.84 (3)
C4—C5	1.392 (5)	O4—O1^iii	1.04 (3)
C5—C6	1.385 (5)	O4—O4^iii	1.70 (3)
C5—H5	0.9300	O1'—O4'^iii	1.30 (2)
C6—C4^ii	1.385 (5)	O1'—O1'^iii	1.52 (2)
C6—H6	0.9300	O2'—O3'^iii	1.39 (2)
N2—N3	1.362 (4)	O3'—O3'^iii	1.33 (2)
Cl1—O1'^iii	1.352 (7)	O3'—O2'^iii	1.39 (2)
Cl1—O1'	1.352 (7)	O4'—O1'^iii	1.30 (2)
Cl1—O3'	1.377 (8)
N1^i—Cu1—N1	174.7 (2)	O2^iii—Cl1—O2	81.3 (17)
N3—C1—N1	109.9 (3)	O1'^iii—Cl1—O3	45.7 (8)
N3—C1—H1	125.1	O1'—Cl1—O3	100.3 (10)
N1—C1—H1	125.1	O3'—Cl1—O3	137.0 (10)
N2—C2—N1	114.0 (4)	O3'^iii—Cl1—O3	79.5 (9)
N2—C2—H2	123.0	O4—Cl1—O3	113.0 (6)
N1—C2—H2	123.0	O4^iii—Cl1—O3	96.1 (12)
N3—C3—C4	110.8 (3)	O2^iii—Cl1—O3	34.4 (12)
N3—C3—H3A	109.5	O2—Cl1—O3	110.5 (7)
C4—C3—H3A	109.5	O1'^iii—Cl1—O3^iii	100.3 (10)
N3—C3—H3B	109.5	O1'—Cl1—O3^iii	45.7 (8)
C4—C3—H3B	109.5	O3'—Cl1—O3^iii	79.5 (9)
H3A—C3—H3B	108.1	O3'^iii—Cl1—O3^iii	137.0 (10)
C6^ii—C4—C5	118.7 (3)	O4—Cl1—O3^iii	96.1 (12)
C6^ii—C4—C3	120.1 (4)	O4^iii—Cl1—O3^iii	113.0 (6)
C5—C4—C3	121.2 (4)	O2^iii—Cl1—O3^iii	110.5 (7)
C6—C5—C4	120.6 (4)	O2—Cl1—O3^iii	34.4 (12)
C6—C5—H5	119.7	O3—Cl1—O3^iii	143.5 (14)
C4—C5—H5	119.7	O1'^iii—Cl1—O1	128.4 (9)
C4^ii—C6—C5	120.7 (4)	O1'—Cl1—O1	80.5 (9)
C4^ii—C6—H6	119.7	O3'—Cl1—O1	71.3 (9)
C5—C6—H6	119.7	O3'^iii—Cl1—O1	80.6 (8)
C1—N1—C2	103.3 (3)	O4—Cl1—O1	107.9 (6)
C1—N1—Cu1	126.1 (3)	O4^iii—Cl1—O1	41.9 (11)
C2—N1—Cu1	130.0 (3)	O2^iii—Cl1—O1	98.1 (11)
C2—N2—N3	102.8 (3)	O2—Cl1—O1	106.1 (6)
C1—N3—N2	110.1 (3)	O3—Cl1—O1	106.0 (7)
C1—N3—C3	129.6 (3)	O3^iii—Cl1—O1	84.1 (7)
N2—N3—C3	120.3 (3)	O1'^iii—Cl1—O1^iii	80.5 (9)
O1'^iii—Cl1—O1'	68.4 (12)	O1'—Cl1—O1^iii	128.4 (9)
O1'^iii—Cl1—O3'	160.2 (8)	O3'—Cl1—O1^iii	80.6 (9)
O1'—Cl1—O3'	120.6 (6)	O3'^iii—Cl1—O1^iii	71.3 (9)
O1'^iii—Cl1—O3'^iii	120.6 (6)	O4—Cl1—O1^iii	41.9 (11)
O1'—Cl1—O3'^iii	160.2 (8)	O4^iii—Cl1—O1^iii	107.9 (6)
O3'—Cl1—O3'^iii	57.6 (12)	O2^iii—Cl1—O1^iii	106.1 (6)
O1'^iii—Cl1—O4	122.4 (9)	O2—Cl1—O1^iii	98.1 (11)
O1'—Cl1—O4	140.8 (10)	O3—Cl1—O1^iii	84.1 (7)
O3'—Cl1—O4	38.9 (7)	O3^iii—Cl1—O1^iii	106.0 (7)
O3'^iii—Cl1—O4	52.4 (8)	O1—Cl1—O1^iii	147.9 (14)
O1'^iii—Cl1—O4^iii	140.8 (10)	O4^iii—O1—Cl1	63.6 (9)
O1'—Cl1—O4^iii	122.4 (9)	O3^iii—O2—Cl1	72.6 (9)
O3'—Cl1—O4^iii	52.4 (8)	O3^iii—O2—O2^iii	114.9 (16)
O3'^iii—Cl1—O4^iii	38.9 (7)	Cl1—O2—O2^iii	49.3 (9)
O4—Cl1—O4^iii	75.2 (17)	O2^iii—O3—Cl1	73.0 (12)
O1'^iii—Cl1—O2^iii	32.0 (9)	O1^iii—O4—Cl1	74.5 (9)
O1'—Cl1—O2^iii	66.0 (8)	O1^iii—O4—O4^iii	115.1 (15)
O3'—Cl1—O2^iii	165.2 (9)	Cl1—O4—O4^iii	52.4 (8)
O3'^iii—Cl1—O2^iii	111.3 (12)	O4'^iii—O1'—Cl1	69.8 (6)
O4—Cl1—O2^iii	144.6 (9)	O4'^iii—O1'—O1'^iii	112.0 (10)
O4^iii—Cl1—O2^iii	112.8 (7)	Cl1—O1'—O1'^iii	55.8 (6)
O1'^iii—Cl1—O2	66.0 (8)	O3'^iii—O2'—Cl1	56.3 (6)
O1'—Cl1—O2	32.0 (9)	O3'^iii—O3'—O2'^iii	118.1 (10)
O3'—Cl1—O2	111.3 (12)	O3'^iii—O3'—Cl1	61.2 (6)
O3'^iii—Cl1—O2	165.2 (9)	O2'^iii—O3'—Cl1	66.3 (6)
O4—Cl1—O2	112.8 (7)	O1'^iii—O4'—Cl1	56.6 (6)
O4^iii—Cl1—O2	144.6 (9)
N3—C3—C4—C6^ii	130.3 (4)	O3'^iii—Cl1—O4—O4^iii	35.7 (10)
N3—C3—C4—C5	−51.0 (5)	O2^iii—Cl1—O4—O4^iii	109 (2)
C6^ii—C4—C5—C6	0.2 (6)	O2—Cl1—O4—O4^iii	−143.4 (10)
C3—C4—C5—C6	−178.5 (4)	O3—Cl1—O4—O4^iii	90.4 (12)
C4—C5—C6—C4^ii	−0.2 (6)	O3^iii—Cl1—O4—O4^iii	−112.3 (8)
N3—C1—N1—C2	−0.9 (4)	O1—Cl1—O4—O4^iii	−26.6 (12)
N3—C1—N1—Cu1	170.7 (2)	O1^iii—Cl1—O4—O4^iii	140 (2)
N2—C2—N1—C1	0.7 (4)	O1'^iii—Cl1—O1'—O4'^iii	−137.2 (12)
N2—C2—N1—Cu1	−170.5 (3)	O3'—Cl1—O1'—O4'^iii	62.5 (11)
N1^i—Cu1—N1—C1	−41.6 (3)	O3'^iii—Cl1—O1'—O4'^iii	−16 (3)
N1^i—Cu1—N1—C2	127.8 (3)	O4—Cl1—O1'—O4'^iii	107.6 (15)
N1—C2—N2—N3	−0.2 (4)	O4^iii—Cl1—O1'—O4'^iii	0.2 (12)
N1—C1—N3—N2	0.9 (4)	O2^iii—Cl1—O1'—O4'^iii	−102.5 (11)
N1—C1—N3—C3	−176.4 (3)	O2—Cl1—O1'—O4'^iii	144 (3)
C2—N2—N3—C1	−0.4 (4)	O3—Cl1—O1'—O4'^iii	−103.8 (13)
C2—N2—N3—C3	177.2 (3)	O3^iii—Cl1—O1'—O4'^iii	91.9 (15)
C4—C3—N3—C1	108.9 (4)	O1—Cl1—O1'—O4'^iii	0.9 (11)
C4—C3—N3—N2	−68.1 (5)	O1^iii—Cl1—O1'—O4'^iii	165.5 (11)
O1'^iii—Cl1—O1—O4^iii	−126.6 (18)	O3'—Cl1—O1'—O1'^iii	−160.3 (8)
O1'—Cl1—O1—O4^iii	−179.1 (16)	O3'^iii—Cl1—O1'—O1'^iii	121 (3)
O3'—Cl1—O1—O4^iii	54.0 (14)	O4—Cl1—O1'—O1'^iii	−115.2 (12)
O3'^iii—Cl1—O1—O4^iii	−4.9 (18)	O4^iii—Cl1—O1'—O1'^iii	137.4 (10)
O4—Cl1—O1—O4^iii	40 (2)	O2^iii—Cl1—O1'—O1'^iii	34.7 (11)
O2^iii—Cl1—O1—O4^iii	−115.3 (14)	O2—Cl1—O1'—O1'^iii	−79 (2)
O2—Cl1—O1—O4^iii	162 (2)	O3—Cl1—O1'—O1'^iii	33.3 (12)
O3—Cl1—O1—O4^iii	−81 (2)	O3^iii—Cl1—O1'—O1'^iii	−131.0 (16)
O3^iii—Cl1—O1—O4^iii	134.8 (15)	O1—Cl1—O1'—O1'^iii	138.1 (11)
O1^iii—Cl1—O1—O4^iii	23.9 (14)	O1^iii—Cl1—O1'—O1'^iii	−57.3 (14)
O1'^iii—Cl1—O2—O3^iii	−178 (3)	O1'^iii—Cl1—O2'—O3'^iii	−133.2 (9)
O1'—Cl1—O2—O3^iii	−90 (2)	O1'—Cl1—O2'—O3'^iii	162.8 (11)
O3'—Cl1—O2—O3^iii	24 (2)	O3'—Cl1—O2'—O3'^iii	29.7 (14)
O3'^iii—Cl1—O2—O3^iii	63 (4)	O4—Cl1—O2'—O3'^iii	−11.3 (13)
O4—Cl1—O2—O3^iii	66 (2)	O4^iii—Cl1—O2'—O3'^iii	46.5 (9)
O4^iii—Cl1—O2—O3^iii	−31 (4)	O2^iii—Cl1—O2'—O3'^iii	−154.7 (13)
O2^iii—Cl1—O2—O3^iii	−148 (3)	O2—Cl1—O2'—O3'^iii	−176.2 (12)
O3—Cl1—O2—O3^iii	−166.7 (15)	O3—Cl1—O2'—O3'^iii	−115.2 (16)
O1—Cl1—O2—O3^iii	−52 (2)	O3^iii—Cl1—O2'—O3'^iii	128.2 (15)
O1^iii—Cl1—O2—O3^iii	107 (2)	O1—Cl1—O2'—O3'^iii	91.5 (11)
O1'^iii—Cl1—O2—O2^iii	−29.4 (9)	O1^iii—Cl1—O2'—O3'^iii	−55.1 (10)
O1'—Cl1—O2—O2^iii	57.9 (19)	O1'^iii—Cl1—O3'—O3'^iii	91 (3)
O3'—Cl1—O2—O2^iii	171.8 (8)	O1'—Cl1—O3'—O3'^iii	−156.9 (10)
O3'^iii—Cl1—O2—O2^iii	−149 (3)	O4—Cl1—O3'—O3'^iii	68.6 (17)
O4—Cl1—O2—O2^iii	−146.1 (10)	O4^iii—Cl1—O3'—O3'^iii	−47.6 (11)
O4^iii—Cl1—O2—O2^iii	117 (2)	O2^iii—Cl1—O3'—O3'^iii	−44 (4)
O3—Cl1—O2—O2^iii	−18.5 (14)	O2—Cl1—O3'—O3'^iii	168.9 (10)
O3^iii—Cl1—O2—O2^iii	148 (3)	O3—Cl1—O3'—O3'^iii	3.2 (18)
O1—Cl1—O2—O2^iii	96.0 (11)	O3^iii—Cl1—O3'—O3'^iii	−177.8 (13)
O1^iii—Cl1—O2—O2^iii	−105.2 (7)	O1—Cl1—O3'—O3'^iii	−90.5 (12)
O1'^iii—Cl1—O3—O2^iii	47.7 (18)	O1^iii—Cl1—O3'—O3'^iii	73.8 (12)
O1'—Cl1—O3—O2^iii	2 (2)	O1'^iii—Cl1—O3'—O2'^iii	−55 (3)
O3'—Cl1—O3—O2^iii	−160.5 (17)	O1'—Cl1—O3'—O2'^iii	57.1 (10)
O3'^iii—Cl1—O3—O2^iii	−158 (2)	O3'^iii—Cl1—O3'—O2'^iii	−146.0 (15)
O4—Cl1—O3—O2^iii	161 (2)	O4—Cl1—O3'—O2'^iii	−77.4 (16)
O4^iii—Cl1—O3—O2^iii	−122.3 (19)	O4^iii—Cl1—O3'—O2'^iii	166.4 (16)
O2—Cl1—O3—O2^iii	34 (3)	O2^iii—Cl1—O3'—O2'^iii	170 (3)
O3^iii—Cl1—O3—O2^iii	21.2 (19)	O2—Cl1—O3'—O2'^iii	22.9 (12)
O1—Cl1—O3—O2^iii	−81 (2)	O3—Cl1—O3'—O2'^iii	−142.8 (13)
O1^iii—Cl1—O3—O2^iii	130.2 (19)	O3^iii—Cl1—O3'—O2'^iii	36.2 (10)
O1'^iii—Cl1—O4—O1^iii	1.0 (19)	O1—Cl1—O3'—O2'^iii	123.5 (11)
O1'—Cl1—O4—O1^iii	96.0 (17)	O1^iii—Cl1—O3'—O2'^iii	−72.2 (10)
O3'—Cl1—O4—O1^iii	172 (3)	O1'—Cl1—O4'—O1'^iii	42.1 (14)
O3'^iii—Cl1—O4—O1^iii	−104.7 (15)	O3'—Cl1—O4'—O1'^iii	174.3 (11)
O4^iii—Cl1—O4—O1^iii	−140 (2)	O3'^iii—Cl1—O4'—O1'^iii	−130.2 (9)
O2^iii—Cl1—O4—O1^iii	−32 (4)	O4—Cl1—O4'—O1'^iii	−179.8 (11)
O2—Cl1—O4—O1^iii	76.2 (15)	O4^iii—Cl1—O4'—O1'^iii	−130.3 (13)
O3—Cl1—O4—O1^iii	−50.0 (16)	O2^iii—Cl1—O4'—O1'^iii	−18.4 (14)
O3^iii—Cl1—O4—O1^iii	107.3 (15)	O2—Cl1—O4'—O1'^iii	63.5 (10)
O1—Cl1—O4—O1^iii	−166.9 (11)	O3—Cl1—O4'—O1'^iii	−51.2 (10)
O1'^iii—Cl1—O4—O4^iii	141.4 (8)	O3^iii—Cl1—O4'—O1'^iii	90.3 (13)
O1'—Cl1—O4—O4^iii	−123.6 (12)	O1—Cl1—O4'—O1'^iii	−105 (4)
O3'—Cl1—O4—O4^iii	−47.3 (14)	O1^iii—Cl1—O4'—O1'^iii	−178 (2)

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x+3/2, −y+1/2, −z+2; (iii) −x+1, y, −z+3/2.