Diaqua­bis[5-(pyrimidin-2-yl-κN)tetrazolato-κN¹]copper(II)

The title compound, [Cu(C₅H₃N₆)₂(H₂O)₂], is isostructural with the manganese(II) analogue, but different from the two-dimensional structures of the zinc(II), iron(II), cobalt(II) and nickel(II) complexes with the same 5-(pyrimidin-2-yl)tetra­zolate ligand. Each of the two symmetry-independent but structurally similar mononuclear mol­ecules in the crystallographic asymmetric unit occupies a special position with the Cu^II atom on an inversion centre. Both Cu^II atoms have a highly distorted octa­hedral coordination geometry formed by two trans water mol­ecules and two chelating ligands. Inter­molecular O—H...N hydrogen bonds are present, which lead to the formation of a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.038
• wR factor = 0.105
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.66
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      36.00 A   3 
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.842(10) ......       3.00 su-Ra
              O1W  -H1WA    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.847(10) ......       3.00 su-Ra
              O2W  -H2WA    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Ra
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O2W  -H3#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.11(3), Rep   2.110(10) ......       3.00 su-Ra
              H1#  -N4      1.555   1.455
PLAT736_ALERT_1_C H...A   Calc     2.03(3), Rep   2.030(10) ......       3.00 su-Ra
              H2#  -N10     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.00(3), Rep   2.000(10) ......       3.00 su-Ra
              H3#  -N9      1.555   1.655

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.658
            Tmax scaled      0.658 Tmin scaled      0.629
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.24
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu2         (2)       2.26
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

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

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

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S1. Comment

The crystal structures of Na^II, Mn^II, Fe^II, Co^II, Ni^II and Zn(II) complexes with 5-(pyrimidin-2-yl)tetrazolate group have been reported recently (Liu & Fan, 2007; Rodríguez et al., 2005, 2007; Rodríguez & Colacio (2006); Zhang et al., 2007). Such complexes were obtained by either the direction reaction of the ligand, 2-(1H-tetrazol-5-yl)pyrimidine or the in situ reaction from pyrimidine-2-carbonitrile in the presence of NaN₃ with metal salts under hydrothermal conditions. Except of the Mn^II complex, which has a mononuclear structure being similar to the title compound, all of other complexes have an extended structure, tow- or three-dimensional. And, the ligands coordinate to metal atoms adopting several modes.

The title complex, Cu(C₅H₃N₆)₂(H₂O)₂ (I) performs a mono-nuclear structure, being similar to that of Mn(II) analog. However, in the crystallographic asymmetric unit, there exist two symmetry-independent but structural similar mononuclear molecules, both of which occupies a special position with Cu^II atoms being on an inversion center (Fig. 1). Two Cu^II centers have a highly distorted octahedral coordination geometry formed by two trans water molecules and two chelating ligand moieties. Table 1 lists the related bond parameters. Furthermore, such molecules are assembled by the intermolecular O—H···N hydrogen bonds to form a two-dimensional network (Fig. 2 and Table 2).

Related literature

For related literature, see: Liu & Fan (2007); Rodríguez et al. (2005, 2007); Rodríguez & Colacio (2006); Zhang et al. (2007).

S2. Experimental

The title compound was synthesized as crystals by a hydrothermal method, with the ligand, 5-(pyrimidin-2-yl)tetrazolato formed during the reaction procedure from the pyrimidine-2-carbonitrile and NaN₃: A mixture of CuCl₂.2H₂O (17 mg, 0.1 mmol), NaN₃ (26 mg, 0.4 mmol) and pyrimidine-2-carbonitrile (21 mg, 0.2 mmol) in water (10 ml) was placed in a Teflon-lined stainless-steel Parr bomb that was heated at 443 K for 48 h. Blue crystals of (I) were collected after the bomb was allowed to cool to room temperature in the period of 24 h. Yield, 20% based on Cu^II. Caution: Azide and tetrazole derivatives are potentially explosive. Although we have met no problems in this work, only a small amount of them should be prepared and handled with great caution.

S3. Refinement

H atoms of organic ligands were included in calculated positions and treated in the subsequent refinement as riding atoms, with C—H = 0.93 Å and U_iso(H) = 1.2 U_eq(C). The H atoms of water molecules were located in Fourier difference map and refined with bond restraints O—H = 0.85 (1) Å, and with U_iso(H) = 1.5 U_eq (O).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SHELXTL (Bruker, 1998); 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 (Sheldrick, 1997).

Figures

	Fig. 1. Displacement ellipsoid plot (30% probability) of (I). [Symmetry codes: (A) -x, -y, 1 - z; (B) 1 - x, -y, -z]
	Fig. 2. Two-dimensional H-bonded network in (I).

Diaquabis[5-(pyrimidin-2-yl-κN)tetrazolato-κN¹]copper(II)

Crystal data

[Cu(C5H3N6)2(H2O)2]	Z = 2
Mr = 393.84	F(000) = 398
Triclinic, P1	Dx = 1.747 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.329 (2) Å	Cell parameters from 5023 reflections
b = 8.107 (2) Å	θ = 3.1–27.5°
c = 12.926 (3) Å	µ = 1.50 mm^−1
α = 86.68 (3)°	T = 293 K
β = 89.84 (3)°	Block, blue
γ = 77.49 (3)°	0.40 × 0.30 × 0.28 mm
V = 748.5 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3433 independent reflections
Radiation source: fine-focus sealed tube	2314 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→9
Tmin = 0.956, Tmax = 1.000	k = −10→10
7532 measured reflections	l = −16→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0465P)^2 + 0.1285P] where P = (Fo^2 + 2Fc^2)/3
3433 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.66 e Å^−3
4 restraints	Δρmin = −0.39 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
Cu1	0.0000	0.0000	0.5000	0.02640 (15)
Cu2	0.5000	0.0000	0.0000	0.02917 (16)
N1	0.2252 (3)	−0.0382 (3)	0.41247 (18)	0.0262 (5)
N2	0.3163 (3)	−0.1505 (3)	0.3476 (2)	0.0314 (6)
N3	0.4635 (3)	−0.0956 (4)	0.3140 (2)	0.0341 (6)
N4	0.4700 (3)	0.0523 (3)	0.35479 (19)	0.0305 (6)
N5	0.1078 (3)	0.2025 (3)	0.53878 (18)	0.0253 (5)
N6	0.3470 (3)	0.3472 (3)	0.4879 (2)	0.0341 (6)
N7	0.2673 (3)	−0.0184 (3)	0.07146 (19)	0.0314 (6)
N8	0.1525 (4)	−0.1263 (4)	0.0808 (2)	0.0406 (7)
N9	0.0165 (4)	−0.0616 (4)	0.1429 (2)	0.0442 (8)
N10	0.0406 (3)	0.0868 (4)	0.1760 (2)	0.0389 (7)
N11	0.4647 (3)	0.2093 (3)	0.08732 (19)	0.0319 (6)
N12	0.2438 (4)	0.3698 (4)	0.1982 (2)	0.0470 (8)
C1	0.3220 (4)	0.0848 (4)	0.4138 (2)	0.0253 (6)
C2	0.2579 (4)	0.2218 (4)	0.4829 (2)	0.0252 (6)
C3	0.2810 (4)	0.4591 (4)	0.5590 (3)	0.0392 (8)
H3A	0.3380	0.5500	0.5653	0.047*
C4	0.1354 (4)	0.4464 (4)	0.6222 (3)	0.0367 (8)
H4A	0.0959	0.5240	0.6722	0.044*
C5	0.0488 (4)	0.3144 (4)	0.6093 (2)	0.0324 (7)
H5A	−0.0526	0.3034	0.6505	0.039*
C6	0.1972 (4)	0.1096 (4)	0.1310 (2)	0.0311 (7)
C7	0.3035 (4)	0.2396 (4)	0.1399 (2)	0.0327 (7)
C8	0.3586 (6)	0.4771 (5)	0.2042 (3)	0.0583 (11)
H8A	0.3225	0.5700	0.2443	0.070*
C9	0.5271 (6)	0.4569 (5)	0.1540 (3)	0.0535 (10)
H9A	0.6044	0.5330	0.1595	0.064*
C10	0.5751 (5)	0.3182 (4)	0.0952 (3)	0.0402 (8)
H10A	0.6880	0.3002	0.0601	0.048*
O1W	−0.1759 (3)	0.1664 (3)	0.35881 (17)	0.0339 (5)
H1WA	−0.279 (3)	0.139 (5)	0.349 (3)	0.051*
H1WB	−0.116 (4)	0.150 (5)	0.3033 (16)	0.051*
O2W	0.6811 (3)	−0.1811 (3)	0.13454 (17)	0.0390 (6)
H2WA	0.780 (3)	−0.146 (5)	0.145 (3)	0.059*
H2WB	0.631 (5)	−0.172 (5)	0.1934 (15)	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0222 (2)	0.0284 (3)	0.0324 (3)	−0.0114 (2)	0.0131 (2)	−0.0119 (2)
Cu2	0.0255 (3)	0.0347 (3)	0.0317 (3)	−0.0132 (2)	0.0132 (2)	−0.0133 (2)
N1	0.0231 (11)	0.0306 (14)	0.0267 (12)	−0.0076 (10)	0.0067 (10)	−0.0088 (11)
N2	0.0269 (12)	0.0342 (15)	0.0335 (14)	−0.0056 (11)	0.0080 (11)	−0.0093 (12)
N3	0.0247 (12)	0.0449 (17)	0.0318 (14)	−0.0045 (11)	0.0080 (11)	−0.0075 (13)
N4	0.0250 (12)	0.0383 (16)	0.0303 (14)	−0.0109 (11)	0.0072 (10)	−0.0029 (12)
N5	0.0229 (11)	0.0243 (13)	0.0299 (13)	−0.0075 (10)	0.0058 (10)	−0.0029 (11)
N6	0.0310 (13)	0.0355 (15)	0.0400 (15)	−0.0161 (11)	0.0054 (11)	−0.0043 (13)
N7	0.0255 (12)	0.0422 (16)	0.0277 (13)	−0.0093 (11)	0.0082 (11)	−0.0059 (12)
N8	0.0333 (14)	0.055 (2)	0.0373 (16)	−0.0170 (13)	0.0068 (12)	−0.0088 (14)
N9	0.0272 (13)	0.071 (2)	0.0380 (16)	−0.0179 (14)	0.0090 (12)	−0.0018 (16)
N10	0.0289 (13)	0.055 (2)	0.0331 (15)	−0.0086 (13)	0.0107 (11)	−0.0049 (14)
N11	0.0317 (13)	0.0349 (15)	0.0307 (14)	−0.0089 (11)	0.0065 (11)	−0.0082 (12)
N12	0.0540 (18)	0.0377 (18)	0.0479 (18)	−0.0039 (14)	0.0142 (15)	−0.0146 (15)
C1	0.0216 (13)	0.0310 (16)	0.0246 (14)	−0.0092 (12)	0.0035 (11)	−0.0003 (12)
C2	0.0207 (12)	0.0277 (15)	0.0287 (15)	−0.0086 (11)	0.0021 (11)	−0.0006 (12)
C3	0.0395 (17)	0.0319 (18)	0.052 (2)	−0.0191 (14)	0.0014 (16)	−0.0077 (16)
C4	0.0395 (17)	0.0320 (18)	0.0411 (19)	−0.0107 (14)	0.0060 (15)	−0.0124 (15)
C5	0.0320 (15)	0.0313 (17)	0.0364 (17)	−0.0097 (13)	0.0092 (13)	−0.0126 (15)
C6	0.0247 (14)	0.0409 (19)	0.0256 (15)	−0.0027 (13)	0.0055 (12)	−0.0003 (14)
C7	0.0345 (16)	0.0343 (18)	0.0265 (15)	−0.0013 (13)	0.0031 (13)	−0.0022 (14)
C8	0.077 (3)	0.038 (2)	0.058 (3)	−0.006 (2)	0.014 (2)	−0.022 (2)
C9	0.069 (3)	0.042 (2)	0.056 (2)	−0.0211 (19)	0.006 (2)	−0.0161 (19)
C10	0.0427 (18)	0.039 (2)	0.0428 (19)	−0.0169 (16)	0.0047 (15)	−0.0087 (16)
O1W	0.0297 (11)	0.0397 (13)	0.0347 (13)	−0.0116 (10)	0.0073 (10)	−0.0071 (11)
O2W	0.0337 (12)	0.0525 (15)	0.0354 (13)	−0.0177 (11)	0.0086 (10)	−0.0097 (12)

Geometric parameters (Å, º)

Cu1—N1	1.977 (2)	N8—N9	1.316 (4)
Cu1—N5	2.057 (2)	N9—N10	1.347 (4)
Cu1—O1W	2.406 (2)	N10—C6	1.328 (4)
Cu2—N7	1.967 (2)	N11—C10	1.328 (4)
Cu2—N11	2.062 (2)	N11—C7	1.345 (4)
Cu2—O2W	2.411 (3)	N12—C7	1.329 (4)
Cu1—N1^i	1.977 (2)	N12—C8	1.340 (5)
Cu1—N5^i	2.057 (2)	C1—C2	1.463 (4)
Cu1—O1W^i	2.406 (2)	C3—C4	1.360 (4)
Cu2—N7^ii	1.967 (2)	C3—H3A	0.9300
Cu2—N11^ii	2.062 (2)	C4—C5	1.375 (4)
Cu2—O2W^ii	2.411 (3)	C4—H4A	0.9300
N1—N2	1.342 (3)	C5—H5A	0.9300
N1—C1	1.344 (4)	C6—C7	1.449 (4)
N2—N3	1.317 (3)	C8—C9	1.376 (5)
N3—N4	1.348 (3)	C8—H8A	0.9300
N4—C1	1.313 (3)	C9—C10	1.375 (4)
N5—C5	1.328 (3)	C9—H9A	0.9300
N5—C2	1.346 (3)	C10—H10A	0.9300
N6—C2	1.326 (4)	O1W—H1WA	0.842 (10)
N6—C3	1.343 (4)	O1W—H1WB	0.841 (10)
N7—N8	1.339 (4)	O2W—H2WA	0.847 (10)
N7—C6	1.339 (4)	O2W—H2WB	0.845 (10)
N1—Cu1—N1^i	180.0	N9—N8—N7	107.5 (3)
N1—Cu1—N5^i	99.14 (9)	N8—N9—N10	110.7 (3)
N1—Cu1—N5	80.86 (9)	C6—N10—N9	104.5 (3)
N1—Cu1—O1W	89.66 (9)	C10—N11—C7	117.2 (3)
N1^i—Cu1—O1W	90.34 (9)	C10—N11—Cu2	129.0 (2)
N5^i—Cu1—N5	180.00 (6)	C7—N11—Cu2	113.8 (2)
N5^i—Cu1—O1W	89.00 (9)	C7—N12—C8	115.4 (3)
N5—Cu1—O1W	91.00 (9)	N4—C1—N1	111.4 (3)
O1W^i—Cu1—O1W	180.00 (7)	N4—C1—C2	130.8 (3)
N1^i—Cu1—N5^i	80.86 (9)	N1—C1—C2	117.7 (2)
N1^i—Cu1—N5	99.14 (9)	N6—C2—N5	126.1 (3)
N1—Cu1—O1W^i	90.34 (9)	N6—C2—C1	120.7 (3)
N1^i—Cu1—O1W^i	89.66 (9)	N5—C2—C1	113.1 (2)
N5^i—Cu1—O1W^i	91.00 (9)	N6—C3—C4	123.5 (3)
N5—Cu1—O1W^i	89.00 (9)	N6—C3—H3A	118.3
N7—Cu2—N7^ii	180.0 (2)	C4—C3—H3A	118.3
N7—Cu2—N11	80.25 (10)	C3—C4—C5	117.4 (3)
N7^ii—Cu2—N11	99.75 (10)	C3—C4—H4A	121.3
N7—Cu2—O2W^ii	89.55 (9)	C5—C4—H4A	121.3
N7—Cu2—O2W	90.45 (9)	N5—C5—C4	121.0 (3)
N11—Cu2—O2W	92.58 (9)	N5—C5—H5A	119.5
N11—Cu2—O2W^ii	87.42 (9)	C4—C5—H5A	119.5
N11—Cu2—N11^ii	180.00 (12)	N10—C6—N7	110.8 (3)
O2W^ii—Cu2—O2W	180.00 (19)	N10—C6—C7	131.7 (3)
N7—Cu2—N11^ii	99.75 (10)	N7—C6—C7	117.4 (3)
N7^ii—Cu2—N11^ii	80.25 (10)	N12—C7—N11	125.8 (3)
N7^ii—Cu2—O2W^ii	90.45 (9)	N12—C7—C6	121.0 (3)
N11^ii—Cu2—O2W^ii	92.58 (9)	N11—C7—C6	113.2 (3)
N7^ii—Cu2—O2W	89.55 (9)	N12—C8—C9	123.4 (3)
N11^ii—Cu2—O2W	87.42 (9)	N12—C8—H8A	118.3
N2—N1—C1	105.9 (2)	C9—C8—H8A	118.3
N2—N1—Cu1	140.0 (2)	C10—C9—C8	116.5 (3)
C1—N1—Cu1	114.09 (18)	C10—C9—H9A	121.7
N3—N2—N1	107.4 (2)	C8—C9—H9A	121.7
N2—N3—N4	110.7 (2)	N11—C10—C9	121.8 (3)
C1—N4—N3	104.6 (2)	N11—C10—H10A	119.1
C5—N5—C2	117.2 (2)	C9—C10—H10A	119.1
C5—N5—Cu1	129.0 (2)	Cu1—O1W—H1WA	112 (3)
C2—N5—Cu1	113.81 (18)	Cu1—O1W—H1WB	110 (3)
C2—N6—C3	114.8 (3)	H1WA—O1W—H1WB	106 (3)
N8—N7—C6	106.5 (2)	Cu2—O2W—H2WA	109 (3)
N8—N7—Cu2	138.6 (2)	Cu2—O2W—H2WB	113 (3)
C6—N7—Cu2	114.9 (2)	H2WA—O2W—H2WB	102 (4)
N5^i—Cu1—N1—N2	−3.7 (3)	N2—N1—C1—N4	−1.3 (3)
N5—Cu1—N1—N2	176.3 (3)	Cu1—N1—C1—N4	179.71 (19)
O1W^i—Cu1—N1—N2	87.4 (3)	N2—N1—C1—C2	−177.1 (2)
O1W—Cu1—N1—N2	−92.6 (3)	Cu1—N1—C1—C2	3.9 (3)
N5^i—Cu1—N1—C1	174.8 (2)	C3—N6—C2—N5	2.6 (5)
N5—Cu1—N1—C1	−5.2 (2)	C3—N6—C2—C1	−176.1 (3)
O1W^i—Cu1—N1—C1	−94.1 (2)	C5—N5—C2—N6	−3.7 (5)
O1W—Cu1—N1—C1	85.9 (2)	Cu1—N5—C2—N6	175.8 (2)
C1—N1—N2—N3	1.1 (3)	C5—N5—C2—C1	175.1 (3)
Cu1—N1—N2—N3	179.7 (2)	Cu1—N5—C2—C1	−5.5 (3)
N1—N2—N3—N4	−0.6 (3)	N4—C1—C2—N6	5.2 (5)
N2—N3—N4—C1	−0.1 (3)	N1—C1—C2—N6	−179.9 (3)
N1^i—Cu1—N5—C5	5.3 (3)	N4—C1—C2—N5	−173.7 (3)
O1W^i—Cu1—N5—C5	−84.2 (3)	N1—C1—C2—N5	1.2 (4)
O1W—Cu1—N5—C5	95.8 (3)	C2—N6—C3—C4	0.5 (5)
N1—Cu1—N5—C2	6.0 (2)	N6—C3—C4—C5	−2.2 (5)
N1^i—Cu1—N5—C2	−174.0 (2)	C2—N5—C5—C4	1.6 (4)
O1W^i—Cu1—N5—C2	96.5 (2)	Cu1—N5—C5—C4	−177.7 (2)
O1W—Cu1—N5—C2	−83.5 (2)	C3—C4—C5—N5	1.1 (5)
N11—Cu2—N7—N8	−174.2 (3)	N9—N10—C6—N7	0.6 (4)
N11^ii—Cu2—N7—N8	5.8 (3)	N9—N10—C6—C7	−175.9 (3)
O2W^ii—Cu2—N7—N8	98.3 (3)	N8—N7—C6—N10	−1.0 (4)
O2W—Cu2—N7—N8	−81.7 (3)	Cu2—N7—C6—N10	179.9 (2)
N11—Cu2—N7—C6	4.4 (2)	N8—N7—C6—C7	176.0 (3)
N11^ii—Cu2—N7—C6	−175.6 (2)	Cu2—N7—C6—C7	−3.0 (4)
O2W^ii—Cu2—N7—C6	−83.0 (2)	C8—N12—C7—N11	−0.7 (5)
O2W—Cu2—N7—C6	97.0 (2)	C8—N12—C7—C6	176.9 (3)
C6—N7—N8—N9	1.1 (4)	C10—N11—C7—N12	0.8 (5)
Cu2—N7—N8—N9	179.8 (2)	Cu2—N11—C7—N12	−177.1 (3)
N7—N8—N9—N10	−0.7 (4)	C10—N11—C7—C6	−176.9 (3)
N8—N9—N10—C6	0.1 (4)	Cu2—N11—C7—C6	5.2 (3)
N7—Cu2—N11—C10	177.1 (3)	N10—C6—C7—N12	−3.1 (6)
N7^ii—Cu2—N11—C10	−2.9 (3)	N7—C6—C7—N12	−179.5 (3)
O2W^ii—Cu2—N11—C10	−92.9 (3)	N10—C6—C7—N11	174.7 (3)
O2W—Cu2—N11—C10	87.1 (3)	N7—C6—C7—N11	−1.6 (4)
N7—Cu2—N11—C7	−5.4 (2)	C7—N12—C8—C9	0.2 (6)
N7^ii—Cu2—N11—C7	174.6 (2)	N12—C8—C9—C10	0.2 (6)
O2W^ii—Cu2—N11—C7	84.6 (2)	C7—N11—C10—C9	−0.4 (5)
O2W—Cu2—N11—C7	−95.4 (2)	Cu2—N11—C10—C9	177.1 (3)
N3—N4—C1—N1	0.9 (3)	C8—C9—C10—N11	0.0 (6)
N3—N4—C1—C2	176.0 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N4^iii	0.84 (1)	2.11 (1)	2.939 (3)	169 (4)
O1W—H1WB···N10	0.84 (1)	2.03 (1)	2.869 (3)	174 (4)
O2W—H2WB···N3	0.85 (1)	2.02 (2)	2.845 (3)	164 (4)
O2W—H2WA···N9^iv	0.85 (1)	2.00 (1)	2.835 (3)	170 (4)

Symmetry codes: (iii) x−1, y, z; (iv) x+1, y, z.