Triaqua-1κO,2κ(2)O-bis-(2,2'-bipyridine)-1κ(2)N,N';2κ(2)N,N'-chlorido-1κCl-μ-terephthalato-1:2κ(2)O(1):O(4)-dicopper(II) nitrate monohydrate.

In the binuclear title compound, [Cu(2)(C(8)H(4)O(4))Cl(C(10)H(8)N(2))(2)(H(2)O)(3)]NO(3)·H(2)O, the two crystallographically independent Cu(II) ions have similar coordination environments. One of the Cu(II) ions has a square-pyramidal arrangement, which is defined by a water mol-ecule occupying the apical position, with the equatorial ligators consisting of two N atoms from a 2,2'-bipyridine mol-ecule, one carboxyl-ate O atom from a terephthalate ligand and one O atom from a water mol-ecule. The other Cu(II) ion has a similar coordination environment, except that the apical position is occupied by a chloride ligand instead of a water mol-ecule. An O-H⋯O and O-H⋯Cl hydrogen-bonded three-dimensional network is formed between the components.

Related literature

For related structures, see: Lo et al. (2000 ▶); Xu et al. (2010 ▶). For background on the use of terephthalic acid and bipyridine as ligands in metal–organic frameworks, see, respectively: Wang et al. (2010 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

[Cu2(C8H4O4)Cl(C10H8N2)2(H2O)3]NO3·H2O

M = 773.08

Triclinic,

a = 10.155 (2) Å

b = 11.204 (2) Å

c = 15.454 (3) Å

α = 76.34 (3)°

β = 83.61 (3)°

γ = 64.90 (3)°

V = 1547.1 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.53 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998 ▶)) T min = 0.750, T max = 0.750

15250 measured reflections

6973 independent reflections

4651 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.172

S = 1.04

6973 reflections

412 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.64 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812019848/fj2542sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019848/fj2542Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu2(C8H4O4)Cl(C10H8N2)2(H2O)3]NO3·H2O	Z = 2
Mr = 773.08	F(000) = 788
Triclinic, P1	Dx = 1.660 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.155 (2) Å	Cell parameters from 9787 reflections
b = 11.204 (2) Å	θ = 3.0–27.5°
c = 15.454 (3) Å	µ = 1.53 mm−1
α = 76.34 (3)°	T = 293 K
β = 83.61 (3)°	Block, blue
γ = 64.90 (3)°	0.20 × 0.20 × 0.20 mm
V = 1547.1 (5) Å3

Rigaku R-AXIS RAPID IP area-detector diffractometer	6973 independent reflections
Radiation source: fine-focus sealed tube	4651 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (Allen et al., 1991)	h = −12→13
Tmin = 0.750, Tmax = 0.750	k = −14→14
15250 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0996P)2] where P = (Fo2 + 2Fc2)/3
6973 reflections	(Δ/σ)max = 0.001
412 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.7820 (5)	−0.0785 (4)	0.9109 (3)	0.0584 (11)
H1	0.7098	−0.0158	0.8713	0.070*
C2	0.9029 (5)	−0.0580 (5)	0.9167 (3)	0.0695 (13)
H2	0.9134	0.0171	0.8812	0.083*
C3	1.0111 (5)	−0.1505 (5)	0.9762 (4)	0.0672 (13)
H3	1.0948	−0.1383	0.9812	0.081*
C4	0.9918 (4)	−0.2604 (5)	1.0278 (3)	0.0582 (11)
H4	1.0615	−0.3226	1.0690	0.070*
C5	0.8687 (4)	−0.2772 (4)	1.0176 (2)	0.0445 (9)
C6	0.8399 (4)	−0.3956 (4)	1.0644 (2)	0.0433 (9)
C7	0.9351 (4)	−0.5015 (4)	1.1251 (3)	0.0529 (10)
H7	1.0217	−0.5010	1.1389	0.063*
C8	0.8985 (5)	−0.6078 (4)	1.1646 (3)	0.0604 (12)
H8	0.9589	−0.6789	1.2068	0.072*
C9	0.7713 (5)	−0.6070 (5)	1.1406 (3)	0.0622 (12)
H9	0.7459	−0.6784	1.1660	0.075*
C10	0.6826 (5)	−0.5008 (4)	1.0793 (3)	0.0567 (11)
H10	0.5975	−0.5014	1.0631	0.068*
C11	0.3524 (4)	−0.0015 (4)	0.8602 (2)	0.0437 (9)
C12	0.2979 (4)	0.1371 (4)	0.8007 (2)	0.0409 (8)
C13	0.3831 (4)	0.2104 (4)	0.7815 (2)	0.0440 (9)
H13	0.4748	0.1742	0.8063	0.053*
C14	0.3321 (4)	0.3363 (4)	0.7260 (2)	0.0469 (9)
H14	0.3890	0.3852	0.7146	0.056*
C15	0.1970 (4)	0.3906 (4)	0.6871 (2)	0.0401 (8)
C16	0.1122 (4)	0.3172 (4)	0.7056 (2)	0.0447 (9)
H16	0.0212	0.3530	0.6797	0.054*
C17	0.1612 (4)	0.1924 (4)	0.7615 (2)	0.0460 (9)
H17	0.1033	0.1445	0.7735	0.055*
C18	0.1432 (4)	0.5279 (4)	0.6280 (2)	0.0439 (9)
C19	−0.1753 (5)	1.0261 (4)	0.4078 (3)	0.0572 (11)
H19	−0.0873	1.0215	0.4236	0.069*
C20	−0.2627 (5)	1.1375 (5)	0.3472 (3)	0.0660 (12)
H20	−0.2348	1.2078	0.3237	0.079*
C21	−0.3912 (5)	1.1430 (5)	0.3221 (3)	0.0628 (12)
H21	−0.4497	1.2157	0.2800	0.075*
C22	−0.4321 (4)	1.0399 (4)	0.3602 (3)	0.0562 (11)
H22	−0.5196	1.0425	0.3452	0.067*
C23	−0.3402 (4)	0.9309 (4)	0.4219 (2)	0.0444 (9)
C24	−0.3718 (4)	0.8138 (4)	0.4664 (3)	0.0471 (9)
C25	−0.4963 (4)	0.7998 (5)	0.4544 (3)	0.0578 (11)
H25	−0.5672	0.8660	0.4154	0.069*
C26	−0.5148 (5)	0.6861 (5)	0.5011 (4)	0.0688 (13)
H26	−0.5976	0.6741	0.4933	0.083*
C27	−0.4091 (5)	0.5916 (5)	0.5591 (3)	0.0707 (14)
H27	−0.4195	0.5146	0.5911	0.085*
C28	−0.2876 (5)	0.6112 (4)	0.5696 (3)	0.0612 (11)
H28	−0.2173	0.5473	0.6099	0.073*
Cl1	−0.17909 (11)	0.86425 (11)	0.67434 (7)	0.0570 (3)
Cu1	0.59529 (5)	−0.23100 (4)	0.95432 (3)	0.04425 (17)
Cu2	−0.09653 (5)	0.75958 (5)	0.53220 (3)	0.04651 (17)
N1	0.7627 (3)	−0.1860 (3)	0.9601 (2)	0.0457 (7)
N2	0.7162 (3)	−0.3949 (3)	1.0418 (2)	0.0450 (7)
N3	−0.2673 (3)	0.7199 (3)	0.5236 (2)	0.0462 (7)
N4	−0.2143 (3)	0.9249 (3)	0.4442 (2)	0.0473 (8)
N5	0.3000 (4)	0.6385 (4)	0.1813 (2)	0.0597 (10)
O1	0.4807 (3)	−0.0500 (3)	0.88775 (19)	0.0536 (7)
O2	0.2685 (3)	−0.0594 (3)	0.8763 (2)	0.0637 (9)
O3	0.0152 (3)	0.5775 (3)	0.59884 (19)	0.0547 (7)
O4	0.2273 (3)	0.5869 (3)	0.6131 (2)	0.0639 (9)
O5	0.0782 (3)	0.7958 (3)	0.5013 (2)	0.0637 (9)
O6	0.4297 (3)	−0.2800 (3)	0.9705 (2)	0.0651 (9)
O7	0.6810 (2)	−0.31174 (19)	0.82969 (13)	0.0757 (9)
O8	0.3190 (2)	0.73970 (19)	0.16260 (13)	0.1204 (16)
O9	0.2562 (2)	0.60351 (19)	0.25133 (13)	0.183 (3)
O10	0.3218 (2)	0.57418 (19)	0.12290 (13)	0.1219 (16)
O11	0.1857 (2)	0.84194 (19)	0.33688 (13)	0.1176 (16)
H5A	0.1636	0.7593	0.5220	0.141*
H5B	0.0846	0.7747	0.4504	0.141*
H6A	0.3714	−0.2463	0.9265	0.141*
H6B	0.3798	−0.2936	1.0171	0.141*
H7A	0.7169	−0.2841	0.7805	0.141*
H7B	0.6878	−0.3903	0.8283	0.141*
H11A	0.2265	0.8103	0.2905	0.141*
H11B	0.1831	0.9200	0.3289	0.141*

	U11	U22	U33	U12	U13	U23
C1	0.054 (2)	0.057 (3)	0.072 (3)	−0.033 (2)	−0.004 (2)	−0.006 (2)
C2	0.069 (3)	0.069 (3)	0.090 (3)	−0.047 (3)	0.006 (3)	−0.020 (3)
C3	0.045 (2)	0.076 (3)	0.100 (4)	−0.035 (2)	0.006 (2)	−0.038 (3)
C4	0.038 (2)	0.076 (3)	0.068 (3)	−0.022 (2)	−0.0039 (19)	−0.031 (2)
C5	0.0328 (19)	0.053 (2)	0.050 (2)	−0.0153 (16)	0.0002 (15)	−0.0207 (18)
C6	0.0358 (19)	0.052 (2)	0.0386 (18)	−0.0123 (16)	−0.0024 (15)	−0.0136 (17)
C7	0.040 (2)	0.057 (2)	0.051 (2)	−0.0039 (18)	−0.0099 (17)	−0.018 (2)
C8	0.062 (3)	0.052 (2)	0.044 (2)	−0.002 (2)	−0.0144 (19)	−0.003 (2)
C9	0.069 (3)	0.056 (3)	0.055 (2)	−0.025 (2)	−0.007 (2)	0.004 (2)
C10	0.057 (3)	0.049 (2)	0.059 (2)	−0.025 (2)	−0.012 (2)	0.008 (2)
C11	0.040 (2)	0.0400 (19)	0.0444 (19)	−0.0133 (16)	−0.0021 (15)	−0.0018 (17)
C12	0.040 (2)	0.0375 (18)	0.0428 (19)	−0.0143 (15)	−0.0020 (15)	−0.0071 (16)
C13	0.0378 (19)	0.0365 (19)	0.052 (2)	−0.0103 (15)	−0.0084 (16)	−0.0046 (17)
C14	0.047 (2)	0.046 (2)	0.051 (2)	−0.0242 (17)	−0.0042 (17)	−0.0021 (18)
C15	0.0408 (19)	0.0366 (18)	0.0383 (18)	−0.0124 (15)	−0.0001 (15)	−0.0063 (16)
C16	0.0362 (19)	0.040 (2)	0.051 (2)	−0.0108 (15)	−0.0090 (16)	−0.0032 (17)
C17	0.045 (2)	0.044 (2)	0.051 (2)	−0.0223 (17)	−0.0038 (17)	−0.0056 (18)
C18	0.038 (2)	0.040 (2)	0.048 (2)	−0.0117 (16)	−0.0022 (16)	−0.0053 (17)
C19	0.054 (2)	0.055 (2)	0.058 (2)	−0.025 (2)	−0.0182 (19)	0.009 (2)
C20	0.075 (3)	0.056 (3)	0.057 (3)	−0.023 (2)	−0.012 (2)	0.003 (2)
C21	0.059 (3)	0.058 (3)	0.050 (2)	−0.007 (2)	−0.017 (2)	0.002 (2)
C22	0.043 (2)	0.064 (3)	0.052 (2)	−0.0077 (19)	−0.0133 (18)	−0.016 (2)
C23	0.038 (2)	0.053 (2)	0.0393 (18)	−0.0120 (17)	−0.0017 (15)	−0.0176 (17)
C24	0.039 (2)	0.056 (2)	0.049 (2)	−0.0161 (17)	0.0027 (16)	−0.0249 (19)
C25	0.038 (2)	0.076 (3)	0.066 (3)	−0.020 (2)	−0.0041 (19)	−0.030 (2)
C26	0.044 (3)	0.081 (3)	0.096 (4)	−0.034 (2)	0.005 (2)	−0.033 (3)
C27	0.069 (3)	0.067 (3)	0.094 (4)	−0.046 (3)	0.015 (3)	−0.022 (3)
C28	0.055 (3)	0.053 (2)	0.077 (3)	−0.027 (2)	0.002 (2)	−0.008 (2)
Cl1	0.0546 (6)	0.0614 (6)	0.0501 (5)	−0.0198 (5)	−0.0087 (4)	−0.0068 (5)
Cu1	0.0352 (3)	0.0418 (3)	0.0544 (3)	−0.0203 (2)	−0.0121 (2)	0.0060 (2)
Cu2	0.0362 (3)	0.0433 (3)	0.0569 (3)	−0.0192 (2)	−0.0132 (2)	0.0064 (2)
N1	0.0398 (17)	0.0490 (18)	0.0527 (18)	−0.0235 (14)	−0.0049 (14)	−0.0068 (15)
N2	0.0414 (17)	0.0428 (17)	0.0480 (17)	−0.0185 (14)	−0.0081 (13)	0.0015 (15)
N3	0.0364 (16)	0.0481 (18)	0.0557 (18)	−0.0184 (14)	−0.0024 (14)	−0.0110 (16)
N4	0.0433 (18)	0.0473 (18)	0.0467 (17)	−0.0185 (14)	−0.0095 (14)	0.0022 (15)
N5	0.063 (2)	0.054 (2)	0.061 (2)	−0.0309 (19)	0.0025 (18)	0.0004 (19)
O1	0.0440 (15)	0.0427 (15)	0.0704 (18)	−0.0214 (12)	−0.0156 (13)	0.0087 (14)
O2	0.0460 (16)	0.0582 (18)	0.080 (2)	−0.0285 (14)	−0.0166 (14)	0.0198 (16)
O3	0.0453 (15)	0.0418 (14)	0.0716 (18)	−0.0203 (12)	−0.0163 (13)	0.0097 (14)
O4	0.0499 (17)	0.0563 (17)	0.080 (2)	−0.0284 (14)	−0.0187 (15)	0.0174 (16)
O5	0.0411 (15)	0.0654 (19)	0.078 (2)	−0.0273 (14)	−0.0164 (14)	0.0138 (16)
O6	0.0430 (15)	0.0609 (18)	0.089 (2)	−0.0323 (14)	−0.0151 (14)	0.0168 (17)
O7	0.096 (3)	0.067 (2)	0.073 (2)	−0.0429 (19)	−0.0019 (18)	−0.0145 (17)
O8	0.142 (4)	0.080 (3)	0.156 (4)	−0.064 (3)	0.007 (3)	−0.027 (3)
O9	0.225 (7)	0.198 (6)	0.123 (4)	−0.118 (6)	0.055 (4)	0.004 (4)
O10	0.114 (4)	0.109 (4)	0.155 (5)	−0.040 (3)	−0.007 (3)	−0.060 (3)
O11	0.174 (5)	0.100 (3)	0.095 (3)	−0.079 (3)	0.039 (3)	−0.027 (3)

C1—N1	1.342 (5)	C20—C21	1.374 (6)
C1—C2	1.358 (6)	C20—H20	0.9300
C1—H1	0.9300	C21—C22	1.373 (6)
C2—C3	1.391 (7)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.397 (5)
C3—C4	1.377 (6)	C22—H22	0.9300
C3—H3	0.9300	C23—N4	1.330 (5)
C4—C5	1.371 (5)	C23—C24	1.476 (5)
C4—H4	0.9300	C24—N3	1.355 (5)
C5—N1	1.358 (5)	C24—C25	1.375 (6)
C5—C6	1.481 (5)	C25—C26	1.385 (6)
C6—N2	1.338 (5)	C25—H25	0.9300
C6—C7	1.388 (5)	C26—C27	1.370 (7)
C7—C8	1.382 (6)	C26—H26	0.9300
C7—H7	0.9300	C27—C28	1.374 (6)
C8—C9	1.379 (6)	C27—H27	0.9300
C8—H8	0.9300	C28—N3	1.342 (5)
C9—C10	1.368 (6)	C28—H28	0.9300
C9—H9	0.9300	Cl1—Cu2	2.6222 (14)
C10—N2	1.355 (5)	Cu1—O1	1.950 (3)
C10—H10	0.9300	Cu1—O6	1.954 (3)
C11—O2	1.246 (4)	Cu1—N1	1.983 (3)
C11—O1	1.260 (4)	Cu1—N2	1.997 (3)
C11—C12	1.507 (5)	Cu1—O7	2.251 (2)
C12—C13	1.393 (5)	Cu2—O3	1.953 (3)
C12—C17	1.400 (5)	Cu2—O5	1.967 (3)
C13—C14	1.379 (5)	Cu2—N3	1.989 (3)
C13—H13	0.9300	Cu2—N4	2.001 (3)
C14—C15	1.385 (5)	N5—O9	1.167 (4)
C14—H14	0.9300	N5—O8	1.194 (4)
C15—C16	1.392 (5)	N5—O10	1.230 (5)
C15—C18	1.495 (5)	O5—H5A	0.8491
C16—C17	1.372 (5)	O5—H5B	0.8602
C16—H16	0.9300	O6—H6A	0.8570
C17—H17	0.9300	O6—H6B	0.8543
C18—O4	1.257 (4)	O7—H7A	0.8545
C18—O3	1.265 (4)	O7—H7B	0.8581
C19—N4	1.337 (5)	O11—H11A	0.8600
C19—C20	1.384 (6)	O11—H11B	0.8431
C19—H19	0.9300
N1—C1—C2	122.5 (4)	N4—C23—C22	121.5 (4)
N1—C1—H1	118.8	N4—C23—C24	114.7 (3)
C2—C1—H1	118.8	C22—C23—C24	123.8 (4)
C1—C2—C3	119.3 (4)	N3—C24—C25	121.7 (4)
C1—C2—H2	120.3	N3—C24—C23	113.7 (3)
C3—C2—H2	120.3	C25—C24—C23	124.5 (4)
C4—C3—C2	118.7 (4)	C24—C25—C26	119.2 (4)
C4—C3—H3	120.6	C24—C25—H25	120.4
C2—C3—H3	120.6	C26—C25—H25	120.4
C5—C4—C3	119.3 (4)	C27—C26—C25	118.8 (4)
C5—C4—H4	120.4	C27—C26—H26	120.6
C3—C4—H4	120.4	C25—C26—H26	120.6
N1—C5—C4	121.8 (4)	C26—C27—C28	119.7 (4)
N1—C5—C6	113.7 (3)	C26—C27—H27	120.2
C4—C5—C6	124.5 (4)	C28—C27—H27	120.2
N2—C6—C7	122.0 (4)	N3—C28—C27	122.0 (4)
N2—C6—C5	114.8 (3)	N3—C28—H28	119.0
C7—C6—C5	123.2 (4)	C27—C28—H28	119.0
C8—C7—C6	118.6 (4)	O1—Cu1—O6	92.65 (12)
C8—C7—H7	120.7	O1—Cu1—N1	91.80 (12)
C6—C7—H7	120.7	O6—Cu1—N1	170.29 (13)
C9—C8—C7	119.1 (4)	O1—Cu1—N2	167.42 (13)
C9—C8—H8	120.5	O6—Cu1—N2	92.88 (12)
C7—C8—H8	120.5	N1—Cu1—N2	81.12 (13)
C10—C9—C8	119.8 (4)	O1—Cu1—O7	92.92 (11)
C10—C9—H9	120.1	O6—Cu1—O7	95.55 (12)
C8—C9—H9	120.1	N1—Cu1—O7	92.84 (11)
N2—C10—C9	121.5 (4)	N2—Cu1—O7	97.78 (11)
N2—C10—H10	119.3	O3—Cu2—O5	92.61 (12)
C9—C10—H10	119.3	O3—Cu2—N3	92.51 (12)
O2—C11—O1	125.6 (3)	O5—Cu2—N3	162.04 (14)
O2—C11—C12	117.6 (3)	O3—Cu2—N4	167.36 (14)
O1—C11—C12	116.8 (3)	O5—Cu2—N4	91.12 (12)
C13—C12—C17	118.9 (3)	N3—Cu2—N4	80.46 (13)
C13—C12—C11	121.3 (3)	O3—Cu2—Cl1	94.28 (10)
C17—C12—C11	119.8 (3)	O5—Cu2—Cl1	98.55 (11)
C14—C13—C12	120.4 (3)	N3—Cu2—Cl1	98.21 (10)
C14—C13—H13	119.8	N4—Cu2—Cl1	97.10 (11)
C12—C13—H13	119.8	C1—N1—C5	118.4 (3)
C13—C14—C15	120.6 (3)	C1—N1—Cu1	126.3 (3)
C13—C14—H14	119.7	C5—N1—Cu1	115.3 (3)
C15—C14—H14	119.7	C6—N2—C10	119.0 (3)
C14—C15—C16	119.1 (3)	C6—N2—Cu1	115.0 (2)
C14—C15—C18	119.7 (3)	C10—N2—Cu1	126.0 (3)
C16—C15—C18	121.2 (3)	C28—N3—C24	118.5 (4)
C17—C16—C15	120.7 (3)	C28—N3—Cu2	126.0 (3)
C17—C16—H16	119.6	C24—N3—Cu2	115.6 (3)
C15—C16—H16	119.6	C23—N4—C19	119.5 (3)
C16—C17—C12	120.3 (3)	C23—N4—Cu2	115.6 (3)
C16—C17—H17	119.9	C19—N4—Cu2	124.9 (3)
C12—C17—H17	119.9	O9—N5—O8	121.9 (4)
O4—C18—O3	125.0 (3)	O9—N5—O10	120.2 (3)
O4—C18—C15	117.4 (3)	O8—N5—O10	117.8 (3)
O3—C18—C15	117.6 (3)	C11—O1—Cu1	128.7 (2)
N4—C19—C20	121.6 (4)	C18—O3—Cu2	128.4 (2)
N4—C19—H19	119.2	Cu2—O5—H5A	133.7
C20—C19—H19	119.2	Cu2—O5—H5B	90.8
C21—C20—C19	119.3 (4)	H5A—O5—H5B	106.8
C21—C20—H20	120.4	Cu1—O6—H6A	115.0
C19—C20—H20	120.4	Cu1—O6—H6B	130.8
C22—C21—C20	119.1 (4)	H6A—O6—H6B	106.7
C22—C21—H21	120.5	Cu1—O7—H7A	134.4
C20—C21—H21	120.5	Cu1—O7—H7B	118.9
C21—C22—C23	119.0 (4)	H7A—O7—H7B	106.5
C21—C22—H22	120.5	H11A—O11—H11B	107.4
C23—C22—H22	120.5
N1—C1—C2—C3	−0.6 (8)	N2—Cu1—N1—C5	−1.9 (3)
C1—C2—C3—C4	−0.1 (8)	O7—Cu1—N1—C5	−99.3 (3)
C2—C3—C4—C5	1.4 (7)	C7—C6—N2—C10	0.1 (6)
C3—C4—C5—N1	−2.2 (6)	C5—C6—N2—C10	178.2 (4)
C3—C4—C5—C6	175.6 (4)	C7—C6—N2—Cu1	179.3 (3)
N1—C5—C6—N2	1.0 (5)	C5—C6—N2—Cu1	−2.5 (4)
C4—C5—C6—N2	−177.0 (4)	C9—C10—N2—C6	1.0 (7)
N1—C5—C6—C7	179.1 (4)	C9—C10—N2—Cu1	−178.2 (4)
C4—C5—C6—C7	1.1 (6)	O1—Cu1—N2—C6	−53.9 (7)
N2—C6—C7—C8	−1.5 (6)	O6—Cu1—N2—C6	−169.9 (3)
C5—C6—C7—C8	−179.5 (4)	N1—Cu1—N2—C6	2.4 (3)
C6—C7—C8—C9	1.9 (7)	O7—Cu1—N2—C6	94.1 (3)
C7—C8—C9—C10	−0.9 (7)	O1—Cu1—N2—C10	125.3 (5)
C8—C9—C10—N2	−0.6 (7)	O6—Cu1—N2—C10	9.3 (4)
O2—C11—C12—C13	178.0 (4)	N1—Cu1—N2—C10	−178.4 (4)
O1—C11—C12—C13	−3.5 (6)	O7—Cu1—N2—C10	−86.7 (4)
O2—C11—C12—C17	−3.9 (6)	C27—C28—N3—C24	1.3 (7)
O1—C11—C12—C17	174.6 (4)	C27—C28—N3—Cu2	−179.7 (4)
C17—C12—C13—C14	1.0 (6)	C25—C24—N3—C28	−0.4 (6)
C11—C12—C13—C14	179.1 (4)	C23—C24—N3—C28	177.9 (4)
C12—C13—C14—C15	−1.3 (6)	C25—C24—N3—Cu2	−179.4 (3)
C13—C14—C15—C16	0.8 (6)	C23—C24—N3—Cu2	−1.1 (4)
C13—C14—C15—C18	179.3 (4)	O3—Cu2—N3—C28	12.5 (4)
C14—C15—C16—C17	−0.1 (6)	O5—Cu2—N3—C28	119.0 (5)
C18—C15—C16—C17	−178.5 (4)	N4—Cu2—N3—C28	−178.1 (4)
C15—C16—C17—C12	−0.2 (6)	Cl1—Cu2—N3—C28	−82.2 (4)
C13—C12—C17—C16	−0.3 (6)	O3—Cu2—N3—C24	−168.5 (3)
C11—C12—C17—C16	−178.4 (4)	O5—Cu2—N3—C24	−62.1 (5)
C14—C15—C18—O4	2.8 (6)	N4—Cu2—N3—C24	0.9 (3)
C16—C15—C18—O4	−178.7 (4)	Cl1—Cu2—N3—C24	96.8 (3)
C14—C15—C18—O3	−175.1 (4)	C22—C23—N4—C19	1.0 (6)
C16—C15—C18—O3	3.3 (6)	C24—C23—N4—C19	−179.9 (4)
N4—C19—C20—C21	−1.5 (8)	C22—C23—N4—Cu2	−179.1 (3)
C19—C20—C21—C22	2.2 (7)	C24—C23—N4—Cu2	0.1 (4)
C20—C21—C22—C23	−1.4 (7)	C20—C19—N4—C23	−0.1 (7)
C21—C22—C23—N4	−0.2 (6)	C20—C19—N4—Cu2	180.0 (4)
C21—C22—C23—C24	−179.3 (4)	O3—Cu2—N4—C23	56.4 (7)
N4—C23—C24—N3	0.7 (5)	O5—Cu2—N4—C23	163.5 (3)
C22—C23—C24—N3	179.9 (4)	N3—Cu2—N4—C23	−0.5 (3)
N4—C23—C24—C25	178.9 (4)	Cl1—Cu2—N4—C23	−97.7 (3)
C22—C23—C24—C25	−1.9 (6)	O3—Cu2—N4—C19	−123.7 (6)
N3—C24—C25—C26	−0.8 (6)	O5—Cu2—N4—C19	−16.5 (4)
C23—C24—C25—C26	−178.9 (4)	N3—Cu2—N4—C19	179.4 (4)
C24—C25—C26—C27	1.0 (7)	Cl1—Cu2—N4—C19	82.2 (4)
C25—C26—C27—C28	−0.1 (8)	O2—C11—O1—Cu1	5.6 (7)
C26—C27—C28—N3	−1.1 (8)	C12—C11—O1—Cu1	−172.8 (2)
C2—C1—N1—C5	−0.1 (7)	O6—Cu1—O1—C11	−7.5 (4)
C2—C1—N1—Cu1	−177.4 (4)	N1—Cu1—O1—C11	−178.9 (4)
C4—C5—N1—C1	1.5 (6)	N2—Cu1—O1—C11	−123.5 (5)
C6—C5—N1—C1	−176.5 (4)	O7—Cu1—O1—C11	88.2 (4)
C4—C5—N1—Cu1	179.1 (3)	O4—C18—O3—Cu2	−5.3 (6)
C6—C5—N1—Cu1	1.0 (4)	C15—C18—O3—Cu2	172.4 (3)
O1—Cu1—N1—C1	−15.0 (4)	O5—Cu2—O3—C18	16.7 (4)
N2—Cu1—N1—C1	175.5 (4)	N3—Cu2—O3—C18	179.5 (4)
O7—Cu1—N1—C1	78.1 (4)	N4—Cu2—O3—C18	123.7 (6)
O1—Cu1—N1—C5	167.7 (3)	Cl1—Cu2—O3—C18	−82.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4	0.85	2.00	2.534 (4)	120
O6—H6A···O2	0.86	1.91	2.511 (4)	126
O6—H6B···O8i	0.86	2.34	3.079 (4)	145
O6—H6B···O10i	0.86	2.14	2.923 (4)	151
O7—H7A···Cl1ii	0.85	2.53	3.325 (2)	156
O7—H7B···O10iii	0.86	2.06	2.869 (3)	157
O11—H11A···O8	0.86	2.26	3.119 (3)	176
O11—H11A···O9	0.86	2.42	3.038 (3)	129
O11—H11B···Cl1iv	0.84	2.39	3.227 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O4	0.85	2.00	2.534 (4)	120
O6—H6A⋯O2	0.86	1.91	2.511 (4)	126
O6—H6B⋯O8i	0.86	2.34	3.079 (4)	145
O6—H6B⋯O10i	0.86	2.14	2.923 (4)	151
O7—H7A⋯Cl1ii	0.85	2.53	3.325 (2)	156
O7—H7B⋯O10iii	0.86	2.06	2.869 (3)	157
O11—H11A⋯O8	0.86	2.26	3.119 (3)	176
O11—H11A⋯O9	0.86	2.42	3.038 (3)	129
O11—H11B⋯Cl1iv	0.84	2.39	3.227 (2)	173

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .