Tetra-kis[(3-hydroxy-prop-yl)dimethyl-ammonium] tetra-μ-acetato-κO:O'-bis-[chloridocuprate(II)](Cu-Cu) dichloride.

The title compound (C(5)H(14)NO)(4)[Cu(2)(CH(3)COO)(4)Cl(2)]Cl(2), consists of a pair of Cu(II) ions bridged by four acetate groups, resulting in a Cu(2)(CH(3)COO)(4) unit, four (3-hydroxy-prop-yl)dimethyl-ammonium cations (two crystallographically independent pairs) and two chloride anions. The Cu atoms at both termini are bonded to chloride anions. The latter are hydrogen bonded to one of the two pairs of crystallographically independent (3-hydroxy-prop-yl)dimethyl-ammonium cations. The Cu(2)(CH(3)COO)(4) unit is located on a crystallographic inversion center, and the geometry around each metal center is close to octa-hedral. The Cl-Cu-Cu angles are nearly linear [177.48 (2)°] and the Cu-O bond lengths are in the range 1.9712 (18)-1.9809 (19) Å. The Cu⋯Cu separation between the two acetate-bridged Cu(II) centers is 2.6793 (8) Å. The packing of the crystal structure is dominated by N-H⋯Cl hydrogen bonding between the ammonium groups and the chloride anions, as well as by O-H⋯O and O-H⋯Cl hydrogen bonds. One of the 3-hydroxypropyldimethylammonium cations shows orientational disorder with an occupancy ratio of 0.812 (4): 0.188 (4).

Related literature

For the structure of binuclear copper(II) complexes, see: Ackermann et al. (2000 ▶); Shahid, Mazhar, Helliwell et al. (2008 ▶). For reports on the X-ray diffraction analysis of cupric acetate hydrate, Cu2(CH3COO)4(H2O)2, see: Van Niekerk & Schoening (1953 ▶); de Meester et al. (1973 ▶); Nieger (2001 ▶); Ferguson & Glidewell (2003 ▶); Steed et al. (1998 ▶); Vives et al. (2003 ▶); Golzar Hossain (2007 ▶); Mahmoudkhani & Langer (1998 ▶). For the neutron-diffraction analysis of the same compound, see: Brown & Chidambaram (1973 ▶). For details concerning the geometric parameters of organo-copper complexes, see: Shahid, Mazhar, Malik et al. (2008 ▶); Shahid et al. (2009 ▶); Zhang et al. (2004 ▶).

Experimental

Crystal data

(C5H14NO)4[Cu2(C2H3O2)4Cl2]Cl2

M = 921.74

Monoclinic,

a = 11.438 (3) Å

b = 11.266 (3) Å

c = 16.876 (4) Å

β = 97.940 (5)°

V = 2153.8 (9) Å3

Z = 2

Mo Kα radiation

μ = 1.29 mm−1

T = 100 K

0.39 × 0.33 × 0.30 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (TWINABS; Sheldrick, 2007 ▶) T min = 0.562, T max = 0.679

19624 measured reflections

5259 independent reflections

4776 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.02

5259 reflections

246 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.67 e Å−3

Δρmin = −0.66 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and CELL NOW (Sheldrick, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900662X/su2095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900662X/su2095Isup2.hkl

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

(C5H14NO)4[Cu2(C2H3O2)4Cl2]Cl2	F(000) = 972
Mr = 921.74	Dx = 1.421 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2075 reflections
a = 11.438 (3) Å	θ = 2.7–30.4°
b = 11.266 (3) Å	µ = 1.29 mm−1
c = 16.876 (4) Å	T = 100 K
β = 97.940 (5)°	Block, green
V = 2153.8 (9) Å3	0.39 × 0.33 × 0.30 mm
Z = 2

Bruker SMART APEX CCD diffractometer	5259 independent reflections
Radiation source: fine-focus sealed tube	4776 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2007)	h = −15→15
Tmin = 0.562, Tmax = 0.679	k = 0→15
19624 measured reflections	l = 0→22

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0511P)2 + 2.2181P] where P = (Fo2 + 2Fc2)/3
5259 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 1.67 e Å−3
1 restraint	Δρmin = −0.66 e Å−3
3 constraints

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	Occ. (<1)
C1	0.7197 (2)	0.9685 (2)	0.54155 (15)	0.0174 (5)
C2	0.8514 (3)	0.9625 (4)	0.5660 (2)	0.0406 (9)
H2A	0.8854	0.9046	0.5323	0.061*
H2B	0.8683	0.9382	0.6221	0.061*
H2C	0.8860	1.0408	0.5593	0.061*
C3	0.4643 (2)	0.7863 (2)	0.45644 (15)	0.0166 (5)
C4	0.4394 (3)	0.6600 (2)	0.42948 (17)	0.0239 (5)
H4A	0.4418	0.6541	0.3718	0.036*
H4B	0.3610	0.6366	0.4411	0.036*
H4C	0.4991	0.6073	0.4580	0.036*
N1	0.7861 (2)	0.7142 (2)	0.78810 (17)	0.0189 (6)	0.812 (4)
H1	0.8449	0.7666	0.7777	0.023*	0.812 (4)
C5	0.7036 (4)	0.6247 (3)	0.5698 (2)	0.0245 (8)	0.812 (4)
H5A	0.6312	0.5809	0.5778	0.029*	0.812 (4)
H5B	0.6797	0.7055	0.5511	0.029*	0.812 (4)
C6	0.7825 (4)	0.6345 (4)	0.6499 (2)	0.0252 (8)	0.812 (4)
H6A	0.8115	0.5548	0.6677	0.030*	0.812 (4)
H6B	0.8517	0.6849	0.6440	0.030*	0.812 (4)
N1B	0.7363 (11)	0.6648 (11)	0.7942 (7)	0.0189 (6)	0.188 (4)
H1B	0.6773	0.6120	0.8038	0.023*	0.188 (4)
C6B	0.7335 (17)	0.6065 (17)	0.6489 (11)	0.0252 (8)	0.188 (4)
H6B1	0.6645	0.5527	0.6406	0.030*	0.188 (4)
H6B2	0.8028	0.5573	0.6695	0.030*	0.188 (4)
C5B	0.7530 (17)	0.6512 (16)	0.5689 (11)	0.0245 (8)	0.188 (4)
H5B1	0.6895	0.7086	0.5505	0.029*	0.188 (4)
H5B2	0.8286	0.6952	0.5752	0.029*	0.188 (4)
C7	0.7144 (3)	0.6879 (3)	0.71129 (18)	0.0278 (6)
H7C	0.7609	0.7597	0.7025	0.033*	0.188 (4)
H7D	0.6304	0.7114	0.7001	0.033*	0.188 (4)
H7A	0.6777	0.7626	0.6892	0.033*	0.812 (4)
H7B	0.6499	0.6333	0.7206	0.033*	0.812 (4)
C8	0.8470 (2)	0.6073 (2)	0.82870 (17)	0.0235 (5)
H8D	0.8953	0.5912	0.7862	0.035*	0.188 (4)
H8E	0.8293	0.5324	0.8541	0.035*	0.188 (4)
H8F	0.8904	0.6598	0.8688	0.035*	0.188 (4)
H8A	0.9118	0.5819	0.8001	0.035*	0.812 (4)
H8B	0.7904	0.5422	0.8295	0.035*	0.812 (4)
H8C	0.8788	0.6291	0.8838	0.035*	0.812 (4)
C9	0.7160 (3)	0.7754 (3)	0.84400 (19)	0.0300 (6)
H9D	0.6966	0.8432	0.8082	0.045*	0.188 (4)
H9E	0.7878	0.7930	0.8809	0.045*	0.188 (4)
H9F	0.6506	0.7606	0.8746	0.045*	0.188 (4)
H9A	0.6952	0.8553	0.8238	0.045*	0.812 (4)
H9B	0.7625	0.7810	0.8973	0.045*	0.812 (4)
H9C	0.6436	0.7302	0.8474	0.045*	0.812 (4)
C10	0.0463 (3)	0.6724 (3)	0.49916 (18)	0.0293 (6)
H10A	−0.0239	0.6212	0.4849	0.035*
H10B	0.0207	0.7563	0.4940	0.035*
C11	0.1022 (3)	0.6472 (3)	0.58522 (18)	0.0283 (6)
H11A	0.0406	0.6491	0.6210	0.034*
H11B	0.1380	0.5670	0.5883	0.034*
C12	0.1966 (3)	0.7392 (3)	0.61261 (18)	0.0267 (6)
H12A	0.2394	0.7589	0.5672	0.032*
H12B	0.1578	0.8125	0.6281	0.032*
C13	0.3698 (3)	0.6112 (3)	0.6563 (2)	0.0321 (7)
H13A	0.4199	0.5798	0.7034	0.048*
H13B	0.4192	0.6507	0.6212	0.048*
H13C	0.3265	0.5459	0.6272	0.048*
C14	0.2309 (3)	0.6569 (3)	0.75181 (19)	0.0360 (7)
H14A	0.1747	0.7164	0.7658	0.054*
H14B	0.2929	0.6449	0.7973	0.054*
H14C	0.1895	0.5818	0.7386	0.054*
Cl1	0.44011 (5)	0.92078 (5)	0.71072 (4)	0.01876 (13)
Cl2	0.99391 (6)	0.88351 (7)	0.77784 (4)	0.03015 (16)
Cu1	0.48200 (3)	0.97068 (2)	0.574297 (18)	0.01280 (8)
N2	0.2843 (2)	0.6984 (2)	0.68207 (14)	0.0217 (5)
H2	0.3285	0.7651	0.6994	0.026*
O1	0.65475 (16)	0.94688 (18)	0.59419 (11)	0.0222 (4)
O2	0.68435 (16)	0.99580 (19)	0.46970 (11)	0.0226 (4)
O3	0.45992 (18)	0.80971 (15)	0.52892 (11)	0.0217 (4)
O4	0.48787 (17)	0.85928 (15)	0.40413 (11)	0.0215 (4)
O5	0.7561 (2)	0.5676 (2)	0.50998 (13)	0.0322 (5)
H5	0.787 (4)	0.506 (3)	0.531 (2)	0.048*
O6	0.13091 (19)	0.6490 (2)	0.44697 (13)	0.0319 (5)
H6	0.0969	0.6451	0.3996	0.048*

	U11	U22	U33	U12	U13	U23
C1	0.0166 (11)	0.0172 (11)	0.0174 (12)	0.0003 (9)	−0.0008 (9)	−0.0002 (9)
C2	0.0172 (13)	0.074 (3)	0.0297 (16)	0.0020 (15)	0.0012 (12)	0.0113 (17)
C3	0.0147 (10)	0.0146 (10)	0.0202 (12)	−0.0002 (9)	0.0012 (9)	−0.0039 (9)
C4	0.0353 (15)	0.0133 (11)	0.0241 (13)	−0.0064 (10)	0.0076 (12)	−0.0036 (10)
N1	0.0184 (13)	0.0156 (13)	0.0238 (13)	−0.0010 (10)	0.0070 (11)	−0.0008 (11)
C5	0.024 (2)	0.0215 (17)	0.0265 (16)	0.0052 (15)	−0.0011 (17)	−0.0015 (14)
C6	0.022 (2)	0.0281 (19)	0.0245 (16)	0.0078 (16)	−0.0001 (16)	−0.0018 (14)
N1B	0.0184 (13)	0.0156 (13)	0.0238 (13)	−0.0010 (10)	0.0070 (11)	−0.0008 (11)
C6B	0.022 (2)	0.0281 (19)	0.0245 (16)	0.0078 (16)	−0.0001 (16)	−0.0018 (14)
C5B	0.024 (2)	0.0215 (17)	0.0265 (16)	0.0052 (15)	−0.0011 (17)	−0.0015 (14)
C7	0.0301 (15)	0.0265 (14)	0.0254 (15)	0.0084 (11)	−0.0015 (12)	−0.0017 (12)
C8	0.0252 (13)	0.0225 (13)	0.0223 (13)	0.0028 (11)	0.0012 (11)	0.0018 (11)
C9	0.0338 (15)	0.0266 (14)	0.0325 (16)	0.0026 (12)	0.0145 (13)	−0.0064 (12)
C10	0.0205 (13)	0.0357 (15)	0.0301 (15)	0.0026 (11)	−0.0019 (11)	−0.0038 (13)
C11	0.0247 (13)	0.0304 (14)	0.0296 (15)	−0.0043 (11)	0.0031 (11)	−0.0016 (12)
C12	0.0274 (14)	0.0220 (13)	0.0288 (15)	0.0013 (11)	−0.0033 (12)	0.0007 (11)
C13	0.0256 (14)	0.0264 (14)	0.0431 (18)	0.0033 (12)	0.0003 (13)	0.0048 (13)
C14	0.0360 (17)	0.0467 (19)	0.0249 (15)	−0.0124 (15)	0.0024 (13)	0.0013 (14)
Cl1	0.0248 (3)	0.0182 (3)	0.0133 (3)	−0.0063 (2)	0.0026 (2)	−0.0005 (2)
Cl2	0.0299 (3)	0.0342 (4)	0.0242 (3)	−0.0153 (3)	−0.0042 (3)	0.0082 (3)
Cu1	0.01441 (13)	0.01100 (13)	0.01291 (14)	−0.00040 (10)	0.00160 (11)	−0.00054 (10)
N2	0.0254 (11)	0.0159 (10)	0.0215 (11)	−0.0030 (9)	−0.0048 (9)	0.0011 (9)
O1	0.0167 (8)	0.0294 (10)	0.0202 (9)	0.0011 (7)	0.0020 (7)	0.0052 (8)
O2	0.0158 (8)	0.0337 (10)	0.0180 (9)	0.0035 (8)	0.0010 (7)	0.0050 (8)
O3	0.0331 (10)	0.0135 (8)	0.0189 (9)	−0.0045 (7)	0.0054 (8)	−0.0026 (7)
O4	0.0332 (10)	0.0129 (8)	0.0187 (9)	−0.0031 (7)	0.0043 (8)	−0.0020 (7)
O5	0.0470 (13)	0.0255 (11)	0.0234 (11)	0.0082 (10)	0.0022 (10)	−0.0015 (9)
O6	0.0281 (10)	0.0425 (13)	0.0235 (10)	0.0065 (10)	−0.0021 (8)	−0.0025 (9)

C1—O1	1.258 (3)	C8—H8F	0.9800
C1—O2	1.262 (3)	C8—H8A	0.9804
C1—C2	1.506 (4)	C8—H8B	0.9801
C2—H2A	0.9800	C8—H8C	0.9821
C2—H2B	0.9800	C9—H9D	0.9800
C2—H2C	0.9800	C9—H9E	0.9800
C3—O3	1.259 (3)	C9—H9F	0.9800
C3—O4	1.262 (3)	C9—H9A	0.9799
C3—C4	1.509 (3)	C9—H9B	0.9824
C4—H4A	0.9800	C9—H9C	0.9805
C4—H4B	0.9800	C10—O6	1.421 (4)
C4—H4C	0.9800	C10—C11	1.531 (4)
N1—C7	1.465 (4)	C10—H10A	0.9900
N1—C9	1.489 (4)	C10—H10B	0.9900
N1—C8	1.508 (4)	C11—C12	1.522 (4)
N1—H1	0.9300	C11—H11A	0.9900
C5—O5	1.399 (4)	C11—H11B	0.9900
C5—C6	1.522 (6)	C12—N2	1.506 (4)
C5—H5A	0.9900	C12—H12A	0.9900
C5—H5B	0.9900	C12—H12B	0.9900
C6—C7	1.505 (5)	C13—N2	1.493 (4)
C6—H6A	0.9900	C13—H13A	0.9800
C6—H6B	0.9900	C13—H13B	0.9800
N1B—C7	1.412 (13)	C13—H13C	0.9800
N1B—C8	1.469 (12)	C14—N2	1.475 (4)
N1B—C9	1.538 (12)	C14—H14A	0.9800
N1B—H1B	0.9300	C14—H14B	0.9800
C6B—C7	1.435 (18)	C14—H14C	0.9800
C6B—C5B	1.49 (3)	Cl1—Cu1	2.4800 (9)
C6B—H6B1	0.9900	Cu1—O3	1.9712 (18)
C6B—H6B2	0.9900	Cu1—O4i	1.9714 (18)
C5B—O5	1.374 (18)	Cu1—O1	1.9762 (19)
C5B—H5B1	0.9900	Cu1—O2i	1.9809 (19)
C5B—H5B2	0.9900	Cu1—Cu1i	2.6793 (8)
C7—H7C	0.9900	N2—H2	0.9300
C7—H7D	0.9900	O2—Cu1i	1.9809 (19)
C7—H7A	0.9902	O4—Cu1i	1.9714 (18)
C7—H7B	0.9902	O5—H5	0.837 (19)
C8—H8D	0.9800	O6—H6	0.8400
C8—H8E	0.9800
O1—C1—O2	125.7 (2)	H8A—C8—H8B	109.5
O1—C1—C2	117.6 (2)	N1—C8—H8C	108.5
O2—C1—C2	116.7 (2)	H8A—C8—H8C	109.4
C1—C2—H2A	109.5	H8B—C8—H8C	109.5
C1—C2—H2B	109.5	N1B—C9—H9D	109.5
H2A—C2—H2B	109.5	N1B—C9—H9E	109.5
C1—C2—H2C	109.5	H9D—C9—H9E	109.5
H2A—C2—H2C	109.5	N1B—C9—H9F	109.5
H2B—C2—H2C	109.5	H9D—C9—H9F	109.5
O3—C3—O4	125.7 (2)	H9E—C9—H9F	109.5
O3—C3—C4	117.3 (2)	N1—C9—H9A	109.4
O4—C3—C4	116.9 (2)	N1—C9—H9B	109.8
C3—C4—H4A	109.5	H9A—C9—H9B	109.5
C3—C4—H4B	109.5	N1—C9—H9C	109.2
H4A—C4—H4B	109.5	H9D—C9—H9C	108.7
C3—C4—H4C	109.5	H9A—C9—H9C	109.4
H4A—C4—H4C	109.5	H9B—C9—H9C	109.5
H4B—C4—H4C	109.5	O6—C10—C11	108.8 (2)
C7—N1—C9	111.7 (2)	O6—C10—H10A	109.9
C7—N1—C8	114.1 (2)	C11—C10—H10A	109.9
C9—N1—C8	109.8 (2)	O6—C10—H10B	109.9
C7—N1—H1	107.0	C11—C10—H10B	109.9
C9—N1—H1	107.0	H10A—C10—H10B	108.3
C8—N1—H1	107.0	C12—C11—C10	110.4 (2)
O5—C5—C6	114.4 (3)	C12—C11—H11A	109.6
O5—C5—H5A	108.6	C10—C11—H11A	109.6
C6—C5—H5A	108.6	C12—C11—H11B	109.6
O5—C5—H5B	108.6	C10—C11—H11B	109.6
C6—C5—H5B	108.6	H11A—C11—H11B	108.1
H5A—C5—H5B	107.6	N2—C12—C11	113.4 (2)
C7—C6—C5	110.0 (3)	N2—C12—H12A	108.9
C7—C6—H6A	109.7	C11—C12—H12A	108.9
C5—C6—H6A	109.7	N2—C12—H12B	108.9
C7—C6—H6B	109.7	C11—C12—H12B	108.9
C5—C6—H6B	109.7	H12A—C12—H12B	107.7
H6A—C6—H6B	108.2	N2—C13—H13A	109.5
C7—N1B—C8	119.9 (8)	N2—C13—H13B	109.5
C7—N1B—C9	111.9 (8)	H13A—C13—H13B	109.5
C8—N1B—C9	109.2 (8)	N2—C13—H13C	109.5
C7—N1B—H1B	104.8	H13A—C13—H13C	109.5
C8—N1B—H1B	104.8	H13B—C13—H13C	109.5
C9—N1B—H1B	104.8	N2—C14—H14A	109.5
C7—C6B—C5B	120.5 (15)	N2—C14—H14B	109.5
C7—C6B—H6B1	107.2	H14A—C14—H14B	109.5
C5B—C6B—H6B1	107.2	N2—C14—H14C	109.5
C7—C6B—H6B2	107.2	H14A—C14—H14C	109.5
C5B—C6B—H6B2	107.2	H14B—C14—H14C	109.5
H6B1—C6B—H6B2	106.8	O3—Cu1—O4i	167.29 (7)
O5—C5B—C6B	116.6 (15)	O3—Cu1—O1	90.72 (8)
O5—C5B—H5B1	108.1	O4i—Cu1—O1	87.44 (8)
C6B—C5B—H5B1	108.1	O3—Cu1—O2i	87.99 (9)
O5—C5B—H5B2	108.1	O4i—Cu1—O2i	91.05 (9)
C6B—C5B—H5B2	108.1	O1—Cu1—O2i	167.32 (8)
H5B1—C5B—H5B2	107.3	O3—Cu1—Cl1	96.96 (6)
N1B—C7—C6B	125.9 (9)	O4i—Cu1—Cl1	95.74 (6)
N1—C7—C6	114.3 (3)	O1—Cu1—Cl1	97.38 (6)
N1B—C7—H7C	105.9	O2i—Cu1—Cl1	95.30 (6)
C6B—C7—H7C	105.9	O3—Cu1—Cu1i	83.76 (6)
N1B—C7—H7D	105.9	O4i—Cu1—Cu1i	83.56 (6)
C6B—C7—H7D	105.9	O1—Cu1—Cu1i	85.02 (6)
H7C—C7—H7D	106.2	O2i—Cu1—Cu1i	82.30 (6)
N1—C7—H7A	108.5	Cl1—Cu1—Cu1i	177.48 (2)
C6—C7—H7A	108.3	C14—N2—C13	112.6 (2)
N1—C7—H7B	108.9	C14—N2—C12	114.4 (2)
C6—C7—H7B	109.2	C13—N2—C12	111.5 (2)
H7A—C7—H7B	107.6	C14—N2—H2	105.9
N1B—C8—H8D	109.5	C13—N2—H2	105.9
N1B—C8—H8E	109.5	C12—N2—H2	105.9
H8D—C8—H8E	109.5	C1—O1—Cu1	121.88 (17)
N1B—C8—H8F	109.5	C1—O2—Cu1i	124.78 (16)
H8D—C8—H8F	109.5	C3—O3—Cu1	123.36 (16)
H8E—C8—H8F	109.5	C3—O4—Cu1i	123.53 (16)
N1—C8—H8A	110.0	C5B—O5—H5	109 (3)
N1—C8—H8B	109.8	C5—O5—H5	106 (3)
H8D—C8—H8B	108.2	C10—O6—H6	109.5
O5—C5—C6—C7	−175.3 (3)	C7—N1B—C9—N1	−67.1 (9)
C7—C6B—C5B—O5	−172.2 (12)	C8—N1B—C9—N1	68.0 (9)
C8—N1B—C7—C6B	45.4 (17)	O6—C10—C11—C12	69.3 (3)
C9—N1B—C7—C6B	175.1 (11)	C10—C11—C12—N2	−159.0 (2)
C8—N1B—C7—N1	−66.4 (10)	C11—C12—N2—C14	−53.9 (3)
C9—N1B—C7—N1	63.3 (8)	C11—C12—N2—C13	75.3 (3)
C8—N1B—C7—C6	14.5 (14)	O2—C1—O1—Cu1	−7.1 (4)
C9—N1B—C7—C6	144.3 (5)	C2—C1—O1—Cu1	172.3 (2)
C5B—C6B—C7—N1B	−155.9 (14)	O3—Cu1—O1—C1	86.9 (2)
C5B—C6B—C7—N1	−114.2 (15)	O4i—Cu1—O1—C1	−80.6 (2)
C5B—C6B—C7—C6	−59.1 (19)	O2i—Cu1—O1—C1	2.8 (5)
C9—N1—C7—N1B	−67.2 (9)	Cl1—Cu1—O1—C1	−176.03 (19)
C8—N1—C7—N1B	57.9 (9)	Cu1i—Cu1—O1—C1	3.18 (19)
C9—N1—C7—C6B	−162.1 (11)	O1—C1—O2—Cu1i	7.4 (4)
C8—N1—C7—C6B	−37.0 (12)	C2—C1—O2—Cu1i	−172.0 (2)
C9—N1—C7—C6	175.5 (3)	O4—C3—O3—Cu1	3.2 (4)
C8—N1—C7—C6	−59.4 (4)	C4—C3—O3—Cu1	−176.89 (18)
C5—C6—C7—N1B	151.0 (7)	O4i—Cu1—O3—C3	−5.5 (5)
C5—C6—C7—C6B	49.7 (18)	O1—Cu1—O3—C3	−87.0 (2)
C5—C6—C7—N1	−173.2 (3)	O2i—Cu1—O3—C3	80.3 (2)
C7—N1B—C8—N1	66.6 (10)	Cl1—Cu1—O3—C3	175.4 (2)
C9—N1B—C8—N1	−64.3 (8)	Cu1i—Cu1—O3—C3	−2.1 (2)
C7—N1—C8—N1B	−57.1 (9)	O3—C3—O4—Cu1i	−2.1 (4)
C9—N1—C8—N1B	69.1 (9)	C4—C3—O4—Cu1i	177.95 (17)
C7—N1—C9—N1B	62.5 (9)	C6B—C5B—O5—C5	54.7 (17)
C8—N1—C9—N1B	−65.1 (9)	C6—C5—O5—C5B	−51.9 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2	0.93	2.15	3.072 (3)	169
N1B—H1B···Cl1ii	0.93	2.53	3.404 (13)	156
N2—H2···Cl1	0.93	2.16	3.074 (2)	166
O5—H5···O6iii	0.84 (2)	1.99 (2)	2.810 (3)	166 (4)
O6—H6···Cl2iv	0.84	2.25	3.082 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl2	0.93	2.15	3.072 (3)	169
N1B—H1B⋯Cl1i	0.93	2.53	3.404 (13)	156
N2—H2⋯Cl1	0.93	2.16	3.074 (2)	166
O5—H5⋯O6ii	0.837 (19)	1.99 (2)	2.810 (3)	166 (4)
O6—H6⋯Cl2iii	0.84	2.25	3.082 (2)	173

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