Related literature {#sec1}
==================

For general background to mol­ecular magnetic materials, see: Stroh *et al.* (2003[@bb7]); Kahn *et al.* (2000[@bb4]); Fursova *et al.* (2003[@bb2]). For complexes including nitronyl nitroxide ligands, see: Muppidi & Pal (2006[@bb5]); Wang *et al.* (2005[@bb10]); Gao *et al.* (2010[@bb3]). For the synthesis of the ligand of the title complex, see: Ullman *et al.* (1970[@bb8], 1972[@bb9]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

\[CuCl~2~(C~11~H~17~N~4~O~2~)~2~\]*M* *~r~* = 609.01Monoclinic,*a* = 7.9966 (10) Å*b* = 14.1981 (18) Å*c* = 12.9266 (17) Åβ = 94.169 (3)°*V* = 1463.8 (3) Å^3^*Z* = 2Mo *K*α radiationμ = 0.97 mm^−1^*T* = 295 K0.43 × 0.27 × 0.17 mm

### Data collection {#sec2.1.2}

Bruker SMART APEXII CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2002[@bb1]) *T* ~min~ = 0.682, *T* ~max~ = 0.85512447 measured reflections3359 independent reflections2607 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.027

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.060*wR*(*F* ^2^) = 0.202*S* = 1.063359 reflections138 parameters63 restraintsH-atom parameters constrainedΔρ~max~ = 1.09 e Å^−3^Δρ~min~ = −1.07 e Å^−3^

 {#d5e420}

Data collection: *SMART* (Bruker, 2002[@bb1]); cell refinement: *SAINT* (Bruker, 2002[@bb1]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb6]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb6]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb6]); software used to prepare material for publication: *publCIF* (Westrip, 2010[@bb11]).

Supplementary Material
======================

Crystal structure: contains datablock(s) I, global. DOI: [10.1107/S1600536811040475/bh2382sup1.cif](http://dx.doi.org/10.1107/S1600536811040475/bh2382sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536811040475/bh2382Isup2.hkl](http://dx.doi.org/10.1107/S1600536811040475/bh2382Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?bh2382&file=bh2382sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?bh2382sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?bh2382&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [BH2382](http://scripts.iucr.org/cgi-bin/sendsup?bh2382)).

This work was supported by the Natural Science Foundation and Basic Research Program of Henan Province (Nos. 092300410195 and 092300410240).

Comment
=======

The design and synthesis of molecule-based magnetic materials is one of the major subjects of material sciences (Stroh *et al.*, 2003; Kahn *et al.*, 2000; Fursova *et al.*, 2003). In this field, nitronyl nitroxides acting as useful paramagnetic building blocks have been extensively used to assemble molecular magnetic materials due to their donor atoms and their ability to assemble extended arrangement with changing magnetic coupling (Muppidi *et al.*, 2006; Wang *et al.*, 2005; Gao *et al.*, 2010). In this article, we report the synthesis and crystal structure of a novel Cu^II^ complex with nitronyl nitroxide radical.

The crystal structure of the title complex is shown in Figures 1 and 2. The copper(II) ion is six-coordinated in a slightly distorted octahedral CuN~2~O~2~Cl~2~ environment. Two nitronyl nitroxide radicals, acting as bidentate chelating ligands, coordinate the Cu^II^ ion leading to two six-membered chelate rings, and the copper coordination is completed by two *trans*-arranged chloride anions.

Experimental {#experimental}
============

The nitronyl nitroxide radical 4,4,5,5-tetramethyl-2-(5-methylimidazol-4-yl)-2-imidazoline-1-oxyl-3-oxide was prepared according to the literature method (Ullman *et al.*, 1970, 1972). The complex was synthesized by mixing 3 ml of an ethanol solution of the radical ligand (0.6 mmol) and 5 ml of an ethanol solution of CuCl~2~.2H~2~O (0.3 mmol). After stirring for two hours at room temperature, the mixture solution was filtered. The clear deep purple filtrate was diffused with diethyl ether vapor at room temperature. Deep purple crystals suitable for X-ray analysis were obtained after a week.

Refinement {#refinement}
==========

All H atoms attached to C atoms were geometrically fixed and allowed to ride on the corresponding parent atom with C---H = 0.96 Å and *U*~iso~(H) = 1.5*U*~eq~(C) for methyl groups or *U*~iso~(H) = 1.2*U*~eq~(C) for other H atoms. Two C atoms in one cycle and the four methyl groups bonded to these atoms (C5, C6, C7, C8, C9, C10) are disordered over two sites. Site occupancies were refined and converged to 0.737 (5) and 0.263 (5). The pair of C---C, C---N 1,2-distances and corresponding 1,3-distances were restrained to be equal within 0.01 Å of each other. The displacement parameters for C5 and C5\', C6 and C6\', C7 and C7\', C8 and C8\', C9 and C9\', C10 and C10\', were constrained to be the same using the *EADP* constraint (Sheldrick, 2008).

Figures
=======

![ORTEP drawing of title compound, showing 30% probability displacement ellipsoids. (H atoms are omitted for clarity) \[symmetry code A: -x, -y, -z +1\]. All disordered atoms are present.](e-67-m1504-fig1){#Fap1}

![ORTEP drawing of the title compound omitting one set of disordered sites. Other features are as in Fig. 1.](e-67-m1504-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ------------------------------------ ---------------------------------------
  \[CuCl~2~(C~11~H~17~N~4~O~2~)~2~\]   *F*(000) = 634
  *M~r~* = 609.01                      *D*~x~ = 1.382 Mg m^−3^
  Monoclinic, *P*2~1~/*c*              Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ybc                 Cell parameters from 5379 reflections
  *a* = 7.9966 (10) Å                  θ = 2.6--28.0°
  *b* = 14.1981 (18) Å                 µ = 0.97 mm^−1^
  *c* = 12.9266 (17) Å                 *T* = 295 K
  β = 94.169 (3)°                      Block, deep purple
  *V* = 1463.8 (3) Å^3^                0.43 × 0.27 × 0.17 mm
  *Z* = 2                              
  ------------------------------------ ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------ --------------------------------------
  Bruker SMART APEXII CCD area-detector diffractometer         3359 independent reflections
  Radiation source: fine-focus sealed tube                     2607 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.027
  φ and ω scans                                                θ~max~ = 27.5°, θ~min~ = 2.6°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2002)   *h* = −10→10
  *T*~min~ = 0.682, *T*~max~ = 0.855                           *k* = −18→18
  12447 measured reflections                                   *l* = −16→16
  ------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- ------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.060   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.202                  H-atom parameters constrained
  *S* = 1.06                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.116*P*)^2^ + 1.4099*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3359 reflections                      (Δ/σ)~max~ \< 0.001
  138 parameters                        Δρ~max~ = 1.09 e Å^−3^
  63 restraints                         Δρ~min~ = −1.07 e Å^−3^
  ------------------------------------- ------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------- --------------- -------------- -------------- -------------------- ------------
          *x*             *y*            *z*            *U*~iso~\*/*U*~eq~   Occ. (\<1)
  C5      0.0161 (3)      0.2896 (2)     0.4252 (2)     0.0550 (10)          0.737 (5)
  C6      0.1823 (3)      0.3180 (2)     0.3766 (3)     0.0604 (15)          0.737 (5)
  C7      −0.1329 (4)     0.2749 (4)     0.3473 (4)     0.093 (3)            0.737 (5)
  H7A     −0.1087         0.2248         0.3008         0.140\*              0.737 (5)
  H7B     −0.1545         0.3318         0.3085         0.140\*              0.737 (5)
  H7C     −0.2297         0.2587         0.3834         0.140\*              0.737 (5)
  C8      −0.0353 (6)     0.3521 (3)     0.5121 (3)     0.086 (2)            0.737 (5)
  H8A     −0.1245         0.3225         0.5460         0.130\*              0.737 (5)
  H8B     −0.0730         0.4117         0.4843         0.130\*              0.737 (5)
  H8C     0.0589          0.3617         0.5614         0.130\*              0.737 (5)
  C9      0.1879 (7)      0.2920 (4)     0.2629 (3)     0.107 (3)            0.737 (5)
  H9A     0.3007          0.2977         0.2430         0.161\*              0.737 (5)
  H9B     0.1160          0.3335         0.2214         0.161\*              0.737 (5)
  H9C     0.1503          0.2282         0.2526         0.161\*              0.737 (5)
  C10     0.2323 (6)      0.4199 (3)     0.3906 (5)     0.108 (3)            0.737 (5)
  H10A    0.2538          0.4333         0.4632         0.162\*              0.737 (5)
  H10B    0.1431          0.4596         0.3622         0.162\*              0.737 (5)
  H10C    0.3317          0.4319         0.3553         0.162\*              0.737 (5)
  C5\'    0.02011 (18)    0.28092 (9)    0.40266 (12)   0.0550 (10)          0.263 (5)
  C6\'    0.1900 (2)      0.33754 (9)    0.41609 (13)   0.0604 (15)          0.263 (5)
  C7\'    −0.02440 (19)   0.24924 (10)   0.29180 (12)   0.093 (3)            0.263 (5)
  H7\'1   −0.0396         0.1822         0.2903         0.140\*              0.263 (5)
  H7\'2   0.0646          0.2660         0.2493         0.140\*              0.263 (5)
  H7\'3   −0.1263         0.2795         0.2657         0.140\*              0.263 (5)
  C8\'    −0.1284 (2)     0.33251 (12)   0.44123 (15)   0.086 (2)            0.263 (5)
  H8\'1   −0.2221         0.2903         0.4420         0.130\*              0.263 (5)
  H8\'2   −0.1574         0.3846         0.3960         0.130\*              0.263 (5)
  H8\'3   −0.1002         0.3555         0.5101         0.130\*              0.263 (5)
  C9\'    0.2417 (3)      0.38454 (12)   0.31841 (15)   0.107 (3)            0.263 (5)
  H9\'1   0.3429          0.4198         0.3339         0.161\*              0.263 (5)
  H9\'2   0.1543          0.4262         0.2919         0.161\*              0.263 (5)
  H9\'3   0.2610          0.3374         0.2674         0.161\*              0.263 (5)
  C10\'   0.2082 (2)      0.40044 (10)   0.51042 (16)   0.108 (3)            0.263 (5)
  H10D    0.2993          0.3784         0.5566         0.162\*              0.263 (5)
  H10E    0.1063          0.3991         0.5453         0.162\*              0.263 (5)
  H10F    0.2305          0.4638         0.4893         0.162\*              0.263 (5)
  Cu1     0.00000 (14)    0.00000 (9)    0.50000 (9)    0.0509 (3)           
  Cl1     0.13233 (14)    0.02450 (8)    0.29756 (8)    0.0751 (4)           
  O1      −0.04541 (13)   0.13931 (9)    0.50405 (9)    0.0500 (6)           
  O2      0.46321 (17)    0.25885 (10)   0.42078 (12)   0.0957 (12)          
  C1      0.31257 (11)    0.10914 (7)    0.54255 (7)    0.0410 (7)           
  C2      0.46835 (14)    0.10640 (9)    0.59493 (10)   0.0482 (8)           
  C3      0.34150 (18)    −0.02968 (9)   0.60589 (10)   0.0512 (8)           
  H3      0.3225          −0.0923        0.6225         0.061\*              
  C4      0.23128 (11)    0.18575 (6)    0.48583 (8)    0.0423 (7)           
  C11     0.60017 (17)    0.17812 (12)   0.62182 (14)   0.0716 (12)          
  H11A    0.5963          0.1960         0.6932         0.107\*              
  H11B    0.5809          0.2325         0.5785         0.107\*              
  H11C    0.7084          0.1521         0.6110         0.107\*              
  N1      0.23258 (13)    0.02450 (7)    0.55218 (8)    0.0426 (6)           
  N2      0.48285 (17)    0.01743 (10)   0.63320 (11)   0.0541 (8)           
  H2      0.5686          −0.0049        0.6690         0.065\*              
  N3      0.06688 (12)    0.19728 (7)    0.47178 (9)    0.0416 (6)           
  N4      0.30710 (15)    0.25572 (8)    0.43551 (10)   0.0597 (8)           
  ------- --------------- -------------- -------------- -------------------- ------------

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ------- ------------- ------------- ------------- -------------- -------------- --------------
          *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  C5      0.0462 (19)   0.047 (2)     0.071 (3)     0.0043 (16)    0.0012 (18)    0.016 (2)
  C6      0.054 (2)     0.061 (3)     0.068 (4)     0.004 (2)      0.018 (2)      0.021 (3)
  C7      0.064 (4)     0.103 (5)     0.109 (5)     −0.009 (4)     −0.024 (3)     0.058 (5)
  C8      0.098 (5)     0.047 (3)     0.120 (6)     0.018 (3)      0.044 (4)      0.005 (3)
  C9      0.105 (6)     0.152 (8)     0.069 (4)     0.021 (6)      0.026 (4)      0.039 (5)
  C10     0.078 (4)     0.055 (4)     0.192 (10)    −0.011 (3)     0.017 (5)      0.020 (5)
  C5\'    0.0462 (19)   0.047 (2)     0.071 (3)     0.0043 (16)    0.0012 (18)    0.016 (2)
  C6\'    0.054 (2)     0.061 (3)     0.068 (4)     0.004 (2)      0.018 (2)      0.021 (3)
  C7\'    0.064 (4)     0.103 (5)     0.109 (5)     −0.009 (4)     −0.024 (3)     0.058 (5)
  C8\'    0.098 (5)     0.047 (3)     0.120 (6)     0.018 (3)      0.044 (4)      0.005 (3)
  C9\'    0.105 (6)     0.152 (8)     0.069 (4)     0.021 (6)      0.026 (4)      0.039 (5)
  C10\'   0.078 (4)     0.055 (4)     0.192 (10)    −0.011 (3)     0.017 (5)      0.020 (5)
  Cu1     0.0331 (3)    0.0363 (3)    0.0801 (5)    0.0035 (2)     −0.0172 (3)    −0.0026 (3)
  Cl1     0.0686 (7)    0.0770 (7)    0.0762 (7)    0.0088 (6)     −0.0188 (5)    −0.0067 (6)
  O1      0.0322 (10)   0.0401 (13)   0.0783 (17)   0.0028 (9)     0.0084 (10)    0.0069 (11)
  O2      0.0425 (16)   0.109 (3)     0.139 (3)     −0.0008 (17)   0.0273 (18)    0.035 (2)
  C1      0.0298 (13)   0.0457 (17)   0.0472 (16)   0.0054 (12)    0.0004 (11)    −0.0064 (13)
  C2      0.0319 (14)   0.056 (2)     0.0561 (19)   0.0057 (14)    0.0002 (13)    −0.0122 (15)
  C3      0.0409 (18)   0.0487 (18)   0.062 (2)     0.0061 (15)    −0.0105 (15)   −0.0021 (16)
  C4      0.0337 (14)   0.0451 (17)   0.0485 (17)   0.0016 (12)    0.0051 (12)    −0.0008 (13)
  C11     0.0376 (18)   0.077 (3)     0.099 (3)     −0.0072 (19)   −0.0075 (19)   −0.019 (2)
  N1      0.0354 (14)   0.0420 (13)   0.0493 (15)   0.0050 (11)    −0.0047 (11)   −0.0029 (11)
  N2      0.0406 (15)   0.0618 (19)   0.0573 (17)   0.0129 (13)    −0.0132 (13)   −0.0074 (14)
  N3      0.0324 (12)   0.0394 (14)   0.0533 (15)   0.0035 (10)    0.0057 (11)    0.0036 (11)
  N4      0.0390 (15)   0.066 (2)     0.076 (2)     −0.0025 (14)   0.0132 (14)    0.0146 (17)
  ------- ------------- ------------- ------------- -------------- -------------- --------------

Geometric parameters (Å, °) {#tablewrapgeomlong}
===========================

  ---------------------------- -------------- ------------------------ --------------
  C5---N3                      1.487 (3)      C8\'---H8\'2             0.9600
  C5---C8                      1.5121         C8\'---H8\'3             0.9600
  C5---C7                      1.5170         C9\'---H9\'1             0.9600
  C5---C6                      1.5639         C9\'---H9\'2             0.9600
  C6---N4                      1.499 (3)      C9\'---H9\'3             0.9600
  C6---C10                     1.5086         C10\'---H10D             0.9600
  C6---C9                      1.5189         C10\'---H10E             0.9600
  C7---H7A                     0.9600         C10\'---H10F             0.9600
  C7---H7B                     0.9600         Cu1---N1                 1.9628
  C7---H7C                     0.9600         Cu1---N1^i^              1.963 (3)
  C8---H8A                     0.9600         Cu1---O1                 2.0123
  C8---H8B                     0.9600         Cu1---O1^i^              2.012 (3)
  C8---H8C                     0.9600         Cu1---Cl1                2.9140
  C9---H9A                     0.9600         O1---N3                  1.3086
  C9---H9B                     0.9600         O2---N4                  1.2772
  C9---H9C                     0.9600         C1---N1                  1.3713
  C10---H10A                   0.9600         C1---C2                  1.3745
  C10---H10B                   0.9600         C1---C4                  1.4401
  C10---H10C                   0.9600         C2---N2                  1.3584
  C5\'---C8\'                  1.5106         C2---C11                 1.4885
  C5\'---N3                    1.5165         C3---N1                  1.3208
  C5\'---C7\'                  1.5193         C3---N2                  1.3385
  C5\'---C6\'                  1.5773         C3---H3                  0.9300
  C6\'---N4                    1.5016         C4---N3                  1.3241
  C6\'---C10\'                 1.5099         C4---N4                  1.3547
  C6\'---C9\'                  1.5121         C11---H11A               0.9600
  C7\'---H7\'1                 0.9600         C11---H11B               0.9600
  C7\'---H7\'2                 0.9600         C11---H11C               0.9600
  C7\'---H7\'3                 0.9600         N2---H2                  0.8600
  C8\'---H8\'1                 0.9600                                  
                                                                       
  N3---C5---C8                 107.3 (2)      H10E---C10\'---H10F      109.5
  N3---C5---C7                 109.0 (2)      N1---Cu1---N1^i^         180.00 (11)
  C8---C5---C7                 109.3          N1---Cu1---O1            89.1
  N3---C5---C6                 100.09 (17)    N1^i^---Cu1---O1         90.85 (11)
  C8---C5---C6                 115.6          N1---Cu1---O1^i^         90.85 (9)
  C7---C5---C6                 114.7          N1^i^---Cu1---O1^i^      89.15 (9)
  N4---C6---C10                110.1 (2)      O1---Cu1---O1^i^         180.00 (13)
  N4---C6---C9                 106.4 (2)      N1---Cu1---Cl1           83.7
  C10---C6---C9                108.9          N1^i^---Cu1---Cl1        96.28 (10)
  N4---C6---C5                 101.38 (18)    O1---Cu1---Cl1           89.1
  C10---C6---C5                115.1          O1^i^---Cu1---Cl1        90.91 (10)
  C9---C6---C5                 114.3          N3---O1---Cu1            118.7
  C8\'---C5\'---N3             110.6          N1---C1---C2             110.0
  C8\'---C5\'---C7\'           108.6          N1---C1---C4             120.8
  N3---C5\'---C7\'             110.8          C2---C1---C4             129.2
  C8\'---C5\'---C6\'           114.1          N2---C2---C1             104.8
  N3---C5\'---C6\'             99.2           N2---C2---C11            120.7
  C7\'---C5\'---C6\'           113.3          C1---C2---C11            134.2
  N4---C6\'---C10\'            107.5          N1---C3---N2             111.1
  N4---C6\'---C9\'             106.0          N1---C3---H3             124.5
  C10\'---C6\'---C9\'          113.4          N2---C3---H3             124.5
  N4---C6\'---C5\'             98.4           N3---C4---N4             108.5
  C10\'---C6\'---C5\'          115.0          N3---C4---C1             124.8
  C9\'---C6\'---C5\'           114.8          N4---C4---C1             126.7
  C5\'---C7\'---H7\'1          109.5          C2---C11---H11A          109.5
  C5\'---C7\'---H7\'2          109.5          C2---C11---H11B          109.5
  H7\'1---C7\'---H7\'2         109.5          H11A---C11---H11B        109.5
  C5\'---C7\'---H7\'3          109.5          C2---C11---H11C          109.5
  H7\'1---C7\'---H7\'3         109.5          H11A---C11---H11C        109.5
  H7\'2---C7\'---H7\'3         109.5          H11B---C11---H11C        109.5
  C5\'---C8\'---H8\'1          109.5          C3---N1---C1             105.3
  C5\'---C8\'---H8\'2          109.5          C3---N1---Cu1            130.5
  H8\'1---C8\'---H8\'2         109.5          C1---N1---Cu1            124.1
  C5\'---C8\'---H8\'3          109.5          C3---N2---C2             108.7
  H8\'1---C8\'---H8\'3         109.5          C3---N2---H2             125.7
  H8\'2---C8\'---H8\'3         109.5          C2---N2---H2             125.7
  C6\'---C9\'---H9\'1          109.5          O1---N3---C4             125.2
  C6\'---C9\'---H9\'2          109.5          O1---N3---C5             120.67 (12)
  H9\'1---C9\'---H9\'2         109.5          C4---N3---C5             113.83 (12)
  C6\'---C9\'---H9\'3          109.5          O1---N3---C5\'           122.3
  H9\'1---C9\'---H9\'3         109.5          C4---N3---C5\'           112.2
  H9\'2---C9\'---H9\'3         109.5          O2---N4---C4             125.0
  C6\'---C10\'---H10D          109.5          O2---N4---C6             121.70 (12)
  C6\'---C10\'---H10E          109.5          C4---N4---C6             111.83 (12)
  H10D---C10\'---H10E          109.5          O2---N4---C6\'           123.5
  C6\'---C10\'---H10F          109.5          C4---N4---C6\'           110.6
  H10D---C10\'---H10F          109.5                                   
                                                                       
  N3---C5---C6---N4            −19.0 (2)      C1---C4---N3---O1        −2.6
  C8---C5---C6---N4            95.9 (3)       N4---C4---N3---C5        −11.16 (16)
  C7---C5---C6---N4            −135.5 (3)     C1---C4---N3---C5        170.75 (16)
  N3---C5---C6---C10           −137.8 (2)     N4---C4---N3---C5\'      2.0
  C8---C5---C6---C10           −23.0          C1---C4---N3---C5\'      −176.1
  C7---C5---C6---C10           105.7          C8---C5---N3---O1        72.32 (16)
  N3---C5---C6---C9            95.0 (2)       C7---C5---N3---O1        −45.98 (16)
  C8---C5---C6---C9            −150.1         C6---C5---N3---O1        −166.68 (13)
  C7---C5---C6---C9            −21.4          C8---C5---N3---C4        −101.31 (18)
  C8\'---C5\'---C6\'---N4      146.8          C7---C5---N3---C4        140.39 (17)
  N3---C5\'---C6\'---N4        29.3           C6---C5---N3---C4        19.68 (19)
  C7\'---C5\'---C6\'---N4      −88.2          C8---C5---N3---C5\'      173.9 (6)
  C8\'---C5\'---C6\'---C10\'   33.0           C7---C5---N3---C5\'      55.6 (5)
  N3---C5\'---C6\'---C10\'     −84.5          C6---C5---N3---C5\'      −65.2 (5)
  C7\'---C5\'---C6\'---C10\'   158.0          C8\'---C5\'---N3---O1    44.7
  C8\'---C5\'---C6\'---C9\'    −101.1         C7\'---C5\'---N3---O1    −75.8
  N3---C5\'---C6\'---C9\'      141.3          C6\'---C5\'---N3---O1    164.9
  C7\'---C5\'---C6\'---C9\'    23.8           C8\'---C5\'---N3---C4    −141.5
  N1---Cu1---O1---N3           42.2           C7\'---C5\'---N3---C4    98.0
  N1^i^---Cu1---O1---N3        −137.83 (10)   C6\'---C5\'---N3---C4    −21.3
  Cl1---Cu1---O1---N3          −41.6          C8\'---C5\'---N3---C5    −41.2 (6)
  N1---C1---C2---N2            2.1            C7\'---C5\'---N3---C5    −161.7 (6)
  C4---C1---C2---N2            −179.4         C6\'---C5\'---N3---C5    79.0 (6)
  N1---C1---C2---C11           −171.6         N3---C4---N4---O2        −169.8
  C4---C1---C2---C11           6.9            C1---C4---N4---O2        8.3
  N1---C1---C4---N3            25.7           N3---C4---N4---C6        −3.46 (17)
  C2---C1---C4---N3            −152.7         C1---C4---N4---C6        174.59 (17)
  N1---C1---C4---N4            −152.0         N3---C4---N4---C6\'      20.5
  C2---C1---C4---N4            29.5           C1---C4---N4---C6\'      −161.5
  N2---C3---N1---C1            2.0            C10---C6---N4---O2       −55.76 (15)
  N2---C3---N1---Cu1           −174.8         C9---C6---N4---O2        62.09 (14)
  C2---C1---N1---C3            −2.5           C5---C6---N4---O2        −178.12 (12)
  C4---C1---N1---C3            178.8          C10---C6---N4---C4       137.42 (16)
  C2---C1---N1---Cu1           174.6          C9---C6---N4---C4        −104.73 (17)
  C4---C1---N1---Cu1           −4.1           C5---C6---N4---C4        15.1 (2)
  O1---Cu1---N1---C3           153.7          C10---C6---N4---C6\'     46.1 (3)
  O1^i^---Cu1---N1---C3        −26.25 (10)    C9---C6---N4---C6\'      163.9 (3)
  Cl1---Cu1---N1---C3          −117.1         C5---C6---N4---C6\'      −76.3 (3)
  O1---Cu1---N1---C1           −22.6          C10\'---C6\'---N4---O2   −82.5
  O1^i^---Cu1---N1---C1        157.41 (10)    C9\'---C6\'---N4---O2    39.1
  Cl1---Cu1---N1---C1          66.6           C5\'---C6\'---N4---O2    157.9
  N1---C3---N2---C2            −0.8           C10\'---C6\'---N4---C4   87.5
  C1---C2---N2---C3            −0.8           C9\'---C6\'---N4---C4    −151.0
  C11---C2---N2---C3           174.0          C5\'---C6\'---N4---C4    −32.1
  Cu1---O1---N3---C4           −36.8          C10\'---C6\'---N4---C6   −175.1 (3)
  Cu1---O1---N3---C5           150.33 (17)    C9\'---C6\'---N4---C6    −53.5 (3)
  Cu1---O1---N3---C5\'         136.2          C5\'---C6\'---N4---C6    65.3 (3)
  N4---C4---N3---O1            175.5                                   
  ---------------------------- -------------- ------------------------ --------------

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