catena-Poly[[[1-benzoyl-2-(2-hydroxy­ethyl)-3-(2-pyrid­yl)­guanidine]­chloridocopper(II)] chloride 0.61-hydrate]

The title copper(II) complex, {[CuCl(C₁₅H₁₆N₄O₂)]Cl·0.61H₂O}_n, is a one-dimensional zigzag coordination polymer structure extending along the (010) direction. The Cu^II atom has a square-pyramidal geometry, where the basal plane is formed by two cis N atoms and one O atom from the ligand, and by a Cl atom. The apical position is occupied by a carbonyl O atom from a symmetry-related mol­ecule. In the crystal structure, there are O-H...Cl and N-H...Cl hydrogen bonds, which link parallel polymer chains along the c direction, so building a two-dimensional structure via the inter­stitial Cl atoms.

S1. Comment

Guanidine chemistry has been extensively studied, as much for its biological activity as for its occurrence in natural products (Bahekar et al., 2007; Berlinck et al., 2005). Guanidines are well established as versatile and flexible ligand systems for a variety of transition metals. Among the important features of these molecules are the donor ability of the nitrogen centers and the potential to explore both the steric and the electronic effects induced by varying organic substituents on the ligand framework (Place et al., 1998). In addition, the N,N',N''-substituted groups allow the design of metal–guanidine fragments with the potential to form coordination polymers. These are of great interest as functional materials with physical properties, such as photoluminescence (Janiak, 2003), nonlinear optical (Lin et al., 2000) and magnetomolecular (Wang et al., 2005). One-dimensional chains are basic building blocks in coordination polymers, and intermolecular interactions play an important role in the structural organization of these complexes (Chen et al., 2006). Recently, a ligand system based on triaminoguanidine with copper(II) has been employed to build a three-dimensional coordination polymer containing two interpenetrating networks of (10,3)-a topology (Zharkouskaya et al., 2005). We report here a new zigzag one-dimensional coordination polymer, (I), obtained by the self-assembly of the cationic fragment [Cu(BHPG)Cl]⁺ on reaction of the guanidine derivative N-benzoyl-N'-(2-hydroxyethyl)-N''-(2-pyridyl)guanidine (BHPG) with copper(II) chloride.

The molecular structure of (I) is illustrated in Fig. 1, and selected geometric parameters are given in Table 1. Complex (I) is a one-dimensional zigzag coordination polymer, with parallel chains extending along the b axis. Each repeating unit is built up of roto-translated complex [Cu(BHPG)Cl]⁺ cations. The square-pyramidal coordinated copper(II) ion lies on a general position, connecting neighboring complex units via the apical carbonyl O1ⁱ atom [symmetry code: (i) -x + 1/2, y + 1/2, -z + 1/2], which is weakly bonded with a distance of 2.417 (2) Å. The coordination polyhedron around copper(II) is square-pyramidal, as indicated by the angular structural parameter τ = (β-α)/60 = 0.051 [Addison et al., 1984; α and β are the angles N1—Cu1—Cl1 = 168.15 (7)° and N4—Cu1—O2 = 171.16 (9)°, respectively]. Looking down the polymer chain, it can be seen that the arrangement of the copper(II) polyhedra is antiparallel, with copper(II) ions separated by a minimun distance of 6.092 Å. The basal plane of the coordination environment is formed by two cis N atoms from the imine and the pyridine groups [with bond distances Cu1—N1 of 1.940 (2) Å and Cu1—N4 of 1.997 (2) Å], a Cl atom and an O atom from the hydroxyl group [with bond distances Cu1—Cl1 of 2.2162 (8) Å and Cu1—O2 of 2.037 (2) Å]. It is interesting to note that the symmetrically substituted guanidine (Zharkouskaya et al., 2005) led to the formation of a three-dimensional polymer with (Cu₃L)⁺ stoichiometry and two distinct metal environments. One of them has a square-pyramidal coordination environment, with a bridging O atom at the apical position with a distance of 2.270 (6) Å, and the other contains a basal plane similar to that of (I), except that the Cu—Cl distance is slightly longer [2.291 (7) Å].

The BHPG ligand acts as a bidentate chelate, leading to the formation of a five-membered ring (Cu1/N1/C2/C3/O3, showing an E form with C2 [or C3?] as the flap atom) and a six-membered ring (Cu1/N1/C1/N2/C11/N4, showing a boat conformation with atoms Cu and N2 as the flap atoms [or `lying out of the plane of the other atoms'? `flap' should probably only apply to `envelopes']). The formation of the six-membered ring and the planarity of the basal plane is an indication of the stability of the complex. The least-squares plane through atoms N4, N1, O2 and Cl1 in the basal plane has an r.m.s. deviation of 0.03 Å, and the Cu^II ion is displaced 0.097 (1) Å above this plane, towards the apical O1ⁱ atom. The bond angles centered at the Cu^II ion sum to 360°.

The cationic complex is counter balanced by a chloride anion, which is at the interstitial position between the parallel polymer chains, allowing the formation of a two-dimensional arrangement extending in the c direction. Thus, the crystal packing (Fig. 2) stabilization is mediated by strong N—H···Cl and O—H···Cl hydrogen bonds (see Table 2 and Fig. 2 for details). The phenyl ring of the toluyl group is rotated to allow compact packing, so the N3—C6—C21—C26 torsion angle becomes -54.4 (4)° and the C6—C21 bond distance, of 1.490 (3) Å, is elongated by 0.03 Å from the expected formal single-bond value as a result of the lack of π–π overlap. In the unit cell, a hydrophobic cavity of volume 476.5 ų, in the vicinity of the inversion center at (0, 1/2, 0) was found to contain a number of very disordered and uncoordinated water molecules. These water molecules are seen in Fig. 2 as three disordered O atoms.

Related literature

For related literature, see: Addison et al. (1984); Bahekar et al. (2007); Berlinck & Kossuga (2005); Chen et al. (2006); Cunha et al. (2001); Janiak (2003); Lin et al. (2000); Place et al. (1998); Wang et al. (2005); Zharkouskaya et al. (2005).

S2. Experimental

The ligand BHPG was synthesized as described by Cunha et al. (2001). A solution containing BHPG (56.8 mg, 0.2 mmol) dissolved in chloroform (5 ml) was added dropwise to a solution containing copper(II) chloride dihydrate (34.1 mg, 0.2 mmol) dissolved in methanol (5 ml). The green mixture was stirred for 2 h at room temperature and evaporated under vacuum (yield 80.8 mg, 96%; m.p. 443–446 K). Analysis calculated for C₁₅H₁₈Cl₂CuN₄O₂: C 42.82, H 4.31, N 13.3%; found: C 43.13, H 4.21, N 12.81%. IR (KBr): ν(C═ N) 1556 (vs) and 1622 (s); ν(C═O) 1681 (s); ν(CH₃) 2936 (m) and 3046 (m) cm^-1. Blue single crystals suitable for X-ray crystallographic analysis were grown in a methanol/ethylacetate ether interface by diffusion.

S3. Refinement

H-atoms H2, H3 and H2C could be located in difference Fourier maps. All the H atoms were included in calculated positions and treated as riding atoms: O—H = 0.82 Å, N—H = 0.86 Å, C—H = 0.93–0.97%A with U_iso(H) = 1.5U_eq(O) and 1.2U_eq(C or N atom). The solvent O atoms were refined with an isotropically restrained displacement tensor (ISOR) and their occupancies were adjusted for an U_eq of ca 0.11 Ų; the solvent site occupation decreased from 1.0 to 0.61. It is worth citing that the solvent site refinement with occupation 1.0 lead to fitting residuals better by 1%, suggesting that one or alternatively two water molecules are fitting the cavity.

Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC (Enraf–Nonius, 1993); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The asymmetric unit of (I), with the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Partial crystal packing diagram of (I), viewed approximately parallel to plane (101); axis b points to the left. Intermolecular hydrogen bonds are shown as dashed lines (only the H atoms involved in hydrogen bonding are shown).

catena-Poly[[[N-benzoyl-N'-(2-hydroxyethyl)-N''-(2-pyridyl)guanidine]chloridocopper(II)] chloride monohydrate]

Crystal data

[CuCl(C15H16N4O2)]Cl·0.61H2O	F(000) = 1753
Mr = 429.75	Dx = 1.546 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 27.022 (3) Å	θ = 11–35°
b = 9.114 (1) Å	µ = 4.50 mm^−1
c = 17.005 (3) Å	T = 297 K
β = 118.116 (10)°	Prism, blue
V = 3693.8 (9) Å^3	0.15 × 0.12 × 0.10 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.037
non–profiled ω/2θ scans	θmax = 67.9°, θmin = 3.7°
Absorption correction: gaussian Spek, 2003	h = −28→32
Tmin = 0.594, Tmax = 0.72	k = −10→10
7066 measured reflections	l = −16→20
3318 independent reflections	2 standard reflections every 120 min
2952 reflections with I > 2σ(I)	intensity decay: 6%

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0946P)^2 + 2.8853P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.048	(Δ/σ)max = 0.015
wR(F^2) = 0.138	Δρmax = 0.48 e Å^−3
S = 1.08	Δρmin = −0.69 e Å^−3
3318 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
246 parameters	Extinction coefficient: 0.00266 (16)
18 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.330209 (16)	0.59634 (4)	0.27069 (3)	0.0415 (2)
Cl1	0.39689 (4)	0.75791 (9)	0.34806 (6)	0.0662 (3)
Cl2	0.18137 (3)	0.52524 (7)	−0.09190 (5)	0.0488 (2)
O1	0.21733 (8)	0.0859 (2)	0.13948 (13)	0.0440 (5)
O2	0.27914 (9)	0.7655 (2)	0.20078 (14)	0.0506 (5)
H2C	0.2913	0.8386	0.1875	0.076*
N1	0.26795 (9)	0.4830 (2)	0.18277 (15)	0.0376 (5)
N2	0.31713 (9)	0.2699 (2)	0.19314 (15)	0.0391 (5)
H2	0.3181	0.1966	0.1621	0.047*
N3	0.22681 (9)	0.2957 (2)	0.07591 (14)	0.0389 (5)
H3	0.2145	0.3454	0.0273	0.047*
N4	0.37349 (9)	0.4121 (2)	0.32230 (16)	0.0416 (5)
C1	0.27086 (10)	0.3553 (3)	0.15410 (16)	0.0350 (5)
C2	0.21557 (11)	0.5666 (3)	0.1469 (2)	0.0438 (6)
H2A	0.2023	0.5735	0.1907	0.053*
H2B	0.1869	0.5193	0.0939	0.053*
C3	0.22848 (12)	0.7173 (3)	0.1245 (2)	0.0476 (7)
H3A	0.2339	0.713	0.072	0.057*
H3B	0.1979	0.7843	0.1127	0.057*
C6	0.20262 (10)	0.1628 (3)	0.07350 (17)	0.0370 (5)
C11	0.36338 (10)	0.2851 (3)	0.27723 (18)	0.0394 (6)
C12	0.39783 (13)	0.1627 (3)	0.3116 (2)	0.0550 (8)
H12	0.3904	0.077	0.2782	0.066*
C13	0.44289 (15)	0.1706 (4)	0.3954 (3)	0.0765 (12)
H13	0.4668	0.0908	0.4196	0.092*
C14	0.45213 (15)	0.3004 (4)	0.4436 (3)	0.0776 (12)
H14	0.482	0.3076	0.5009	0.093*
C15	0.41731 (14)	0.4165 (4)	0.4062 (2)	0.0580 (8)
H15	0.4237	0.5022	0.4393	0.07*
C21	0.15740 (11)	0.1169 (3)	−0.01567 (18)	0.0390 (6)
C22	0.16135 (13)	−0.0202 (3)	−0.0464 (2)	0.0483 (7)
H22	0.192	−0.0799	−0.0124	0.058*
C23	0.11976 (14)	−0.0692 (4)	−0.1280 (2)	0.0567 (8)
H23	0.1225	−0.1613	−0.149	0.058 (10)*
C24	0.07412 (13)	0.0193 (5)	−0.1780 (2)	0.0652 (9)
H24	0.0463	−0.0129	−0.233	0.078*
C25	0.06964 (13)	0.1548 (5)	−0.1466 (2)	0.0666 (9)
H25	0.0384	0.2129	−0.1801	0.08*
C26	0.11144 (12)	0.2061 (4)	−0.0652 (2)	0.0530 (7)
H26	0.1086	0.2985	−0.0444	0.064*
O11	0.0407 (10)	0.508 (2)	−0.181 (3)	0.124 (10)	0.18
O12	0.0136 (10)	0.604 (2)	−0.221 (3)	0.124 (14)	0.18
O13	0.0455 (9)	0.564 (3)	−0.1229 (18)	0.129 (7)	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0450 (3)	0.0288 (3)	0.0464 (3)	−0.00345 (14)	0.0179 (2)	−0.00371 (14)
Cl1	0.0678 (5)	0.0441 (4)	0.0685 (5)	−0.0204 (3)	0.0170 (4)	−0.0064 (3)
Cl2	0.0574 (4)	0.0352 (4)	0.0533 (4)	0.0035 (3)	0.0257 (3)	0.0010 (3)
O1	0.0487 (10)	0.0378 (10)	0.0427 (10)	−0.0018 (7)	0.0194 (9)	0.0057 (8)
O2	0.0636 (12)	0.0287 (9)	0.0544 (11)	0.0000 (8)	0.0237 (10)	0.0029 (8)
N1	0.0383 (10)	0.0287 (10)	0.0430 (11)	0.0033 (8)	0.0168 (9)	−0.0012 (9)
N2	0.0388 (10)	0.0287 (10)	0.0453 (12)	0.0022 (8)	0.0162 (9)	−0.0046 (9)
N3	0.0432 (11)	0.0298 (10)	0.0360 (10)	−0.0021 (8)	0.0123 (9)	0.0018 (8)
N4	0.0372 (11)	0.0361 (11)	0.0453 (12)	−0.0022 (8)	0.0143 (10)	−0.0024 (9)
C1	0.0359 (12)	0.0298 (12)	0.0392 (12)	−0.0012 (9)	0.0176 (10)	0.0013 (10)
C2	0.0425 (13)	0.0337 (12)	0.0534 (15)	0.0061 (11)	0.0211 (12)	−0.0015 (12)
C3	0.0570 (16)	0.0345 (13)	0.0508 (15)	0.0087 (12)	0.0249 (13)	0.0064 (12)
C6	0.0367 (12)	0.0325 (12)	0.0427 (13)	0.0008 (9)	0.0194 (11)	−0.0007 (10)
C11	0.0353 (12)	0.0345 (12)	0.0453 (13)	−0.0002 (10)	0.0165 (11)	0.0023 (11)
C12	0.0466 (15)	0.0395 (15)	0.0640 (19)	0.0078 (12)	0.0137 (14)	0.0008 (13)
C13	0.0564 (19)	0.055 (2)	0.081 (2)	0.0146 (16)	0.0021 (18)	0.0079 (18)
C14	0.059 (2)	0.065 (2)	0.066 (2)	0.0034 (16)	−0.0063 (17)	0.0012 (18)
C15	0.0498 (16)	0.0506 (18)	0.0541 (18)	−0.0049 (13)	0.0084 (14)	−0.0057 (14)
C21	0.0363 (12)	0.0378 (13)	0.0407 (13)	−0.0051 (10)	0.0165 (11)	0.0010 (10)
C22	0.0512 (15)	0.0395 (14)	0.0496 (15)	−0.0043 (12)	0.0200 (13)	−0.0005 (12)
C23	0.0599 (19)	0.0533 (17)	0.0582 (18)	−0.0181 (14)	0.0290 (16)	−0.0166 (15)
C24	0.0442 (15)	0.086 (3)	0.0565 (19)	−0.0182 (16)	0.0159 (14)	−0.0198 (18)
C25	0.0371 (14)	0.082 (2)	0.0615 (19)	0.0044 (15)	0.0079 (14)	−0.0025 (18)
C26	0.0403 (14)	0.0530 (17)	0.0554 (17)	0.0017 (12)	0.0139 (13)	−0.0020 (14)
O11	0.085 (13)	0.068 (12)	0.24 (3)	0.027 (10)	0.092 (18)	0.010 (16)
O12	0.09 (2)	0.084 (12)	0.21 (5)	0.004 (11)	0.08 (2)	0.006 (15)
O13	0.107 (13)	0.114 (14)	0.21 (2)	−0.015 (11)	0.110 (17)	−0.006 (15)

Geometric parameters (Å, º)

Cu1—N1	1.940 (2)	C3—H3B	0.97
Cu1—N4	1.997 (2)	C6—C21	1.490 (3)
Cu1—O2	2.037 (2)	C11—C12	1.393 (4)
Cu1—Cl1	2.2162 (8)	C12—C13	1.373 (5)
Cu1—O1^i	2.417 (2)	C12—H12	0.93
O1—C6	1.220 (3)	C13—C14	1.393 (6)
O1—Cu1^ii	2.417 (2)	C13—H13	0.93
O2—C3	1.441 (4)	C14—C15	1.358 (5)
O2—H2C	0.82	C14—H14	0.93
N1—C1	1.278 (3)	C15—H15	0.93
N1—C2	1.464 (3)	C21—C22	1.378 (4)
N2—C1	1.352 (3)	C21—C26	1.388 (4)
N2—C11	1.394 (3)	C22—C23	1.384 (4)
N2—H2	0.86	C22—H22	0.93
N3—C6	1.367 (3)	C23—C24	1.381 (5)
N3—C1	1.410 (3)	C23—H23	0.93
N3—H3	0.86	C24—C25	1.372 (6)
N4—C11	1.343 (3)	C24—H24	0.93
N4—C15	1.359 (4)	C25—C26	1.391 (4)
C2—C3	1.509 (4)	C25—H25	0.93
C2—H2A	0.97	C26—H26	0.93
C2—H2B	0.97	O12—O12^iii	0.90 (6)
C3—H3A	0.97
N1—Cu1—N4	90.38 (9)	C2—C3—H3B	110.4
N1—Cu1—O2	81.39 (8)	H3A—C3—H3B	108.6
N4—Cu1—O2	171.16 (9)	O1—C6—N3	122.5 (2)
N1—Cu1—Cl1	168.15 (7)	O1—C6—C21	122.0 (2)
N4—Cu1—Cl1	98.85 (7)	N3—C6—C21	115.5 (2)
O2—Cu1—Cl1	88.92 (7)	N4—C11—C12	122.3 (2)
N1—Cu1—O1^i	86.55 (8)	N4—C11—N2	121.0 (2)
N4—Cu1—O1^i	93.70 (9)	C12—C11—N2	116.7 (2)
O2—Cu1—O1^i	89.03 (8)	C13—C12—C11	118.9 (3)
Cl1—Cu1—O1^i	100.17 (5)	C13—C12—H12	120.5
C6—O1—Cu1^ii	121.24 (17)	C11—C12—H12	120.5
C3—O2—Cu1	112.91 (15)	C12—C13—C14	118.7 (3)
C3—O2—H2C	109.5	C12—C13—H13	120.6
Cu1—O2—H2C	121.8	C14—C13—H13	120.6
C1—N1—C2	122.4 (2)	C15—C14—C13	119.6 (3)
C1—N1—Cu1	126.29 (17)	C15—C14—H14	120.2
C2—N1—Cu1	111.16 (17)	C13—C14—H14	120.2
C1—N2—C11	128.4 (2)	C14—C15—N4	122.5 (3)
C1—N2—H2	115.8	C14—C15—H15	118.7
C11—N2—H2	115.8	N4—C15—H15	118.7
C6—N3—C1	123.3 (2)	C22—C21—C26	120.5 (3)
C6—N3—H3	118.4	C22—C21—C6	117.9 (2)
C1—N3—H3	118.4	C26—C21—C6	121.5 (3)
C11—N4—C15	117.8 (2)	C21—C22—C23	120.1 (3)
C11—N4—Cu1	123.65 (18)	C21—C22—H22	120
C15—N4—Cu1	118.5 (2)	C23—C22—H22	120
N1—C1—N2	123.1 (2)	C24—C23—C22	119.8 (3)
N1—C1—N3	122.3 (2)	C24—C23—H23	120.1
N2—C1—N3	114.5 (2)	C22—C23—H23	120.1
N1—C2—C3	106.6 (2)	C25—C24—C23	120.2 (3)
N1—C2—H2A	110.4	C25—C24—H24	119.9
C3—C2—H2A	110.4	C23—C24—H24	119.9
N1—C2—H2B	110.4	C24—C25—C26	120.7 (3)
C3—C2—H2B	110.4	C24—C25—H25	119.7
H2A—C2—H2B	108.6	C26—C25—H25	119.7
O2—C3—C2	106.5 (2)	C21—C26—C25	118.8 (3)
O2—C3—H3A	110.4	C21—C26—H26	120.6
C2—C3—H3A	110.4	C25—C26—H26	120.6
O2—C3—H3B	110.4
N1—Cu1—O2—C3	−3.42 (19)	Cu1^ii—O1—C6—N3	94.5 (3)
Cl1—Cu1—O2—C3	169.73 (19)	Cu1^ii—O1—C6—C21	−86.4 (3)
O1^i—Cu1—O2—C3	−90.08 (19)	C1—N3—C6—O1	0.4 (4)
N4—Cu1—N1—C1	−25.1 (2)	C1—N3—C6—C21	−178.8 (2)
O2—Cu1—N1—C1	151.7 (2)	C15—N4—C11—C12	−3.6 (4)
Cl1—Cu1—N1—C1	116.2 (3)	Cu1—N4—C11—C12	173.2 (2)
O1^i—Cu1—N1—C1	−118.8 (2)	C15—N4—C11—N2	176.0 (3)
N4—Cu1—N1—C2	158.8 (2)	Cu1—N4—C11—N2	−7.2 (4)
O2—Cu1—N1—C2	−24.43 (18)	C1—N2—C11—N4	−16.8 (4)
Cl1—Cu1—N1—C2	−59.9 (4)	C1—N2—C11—C12	162.8 (3)
O1^i—Cu1—N1—C2	65.12 (19)	N4—C11—C12—C13	1.8 (5)
N1—Cu1—N4—C11	22.0 (2)	N2—C11—C12—C13	−177.9 (3)
Cl1—Cu1—N4—C11	−150.5 (2)	C11—C12—C13—C14	0.8 (6)
O1^i—Cu1—N4—C11	108.6 (2)	C12—C13—C14—C15	−1.3 (7)
N1—Cu1—N4—C15	−161.1 (3)	C13—C14—C15—N4	−0.7 (7)
Cl1—Cu1—N4—C15	26.3 (3)	C11—N4—C15—C14	3.1 (5)
O1^i—Cu1—N4—C15	−74.6 (2)	Cu1—N4—C15—C14	−173.9 (3)
C2—N1—C1—N2	−172.2 (3)	O1—C6—C21—C22	−51.2 (4)
Cu1—N1—C1—N2	12.1 (4)	N3—C6—C21—C22	128.0 (3)
C2—N1—C1—N3	11.4 (4)	O1—C6—C21—C26	126.4 (3)
Cu1—N1—C1—N3	−164.32 (18)	N3—C6—C21—C26	−54.4 (4)
C11—N2—C1—N1	14.9 (4)	C26—C21—C22—C23	1.0 (5)
C11—N2—C1—N3	−168.4 (2)	C6—C21—C22—C23	178.6 (3)
C6—N3—C1—N1	−125.5 (3)	C21—C22—C23—C24	−0.5 (5)
C6—N3—C1—N2	57.8 (3)	C22—C23—C24—C25	−0.7 (5)
C1—N1—C2—C3	−129.6 (3)	C23—C24—C25—C26	1.4 (6)
Cu1—N1—C2—C3	46.7 (3)	C22—C21—C26—C25	−0.3 (5)
Cu1—O2—C3—C2	28.9 (3)	C6—C21—C26—C25	−177.8 (3)
N1—C2—C3—O2	−47.6 (3)	C24—C25—C26—C21	−0.9 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2C···Cl2^iv	0.82	2.42	3.173 (2)	153
N2—H2···Cl2^v	0.86	2.35	3.204 (2)	172
N3—H3···Cl2	0.86	2.43	3.275 (2)	169

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