Synthesis, crystal structures and characterizations of three new copper(II) complexes including anti-inflammatory diclofenac

Three new diclofenac-based copper(II) complexes, namely tetra­kis­{μ-2-[2-(2,6-di­chloro­anilino)phen­yl]acetato-κ²O:O′}bis­(methanol-κO)copper(II), [Cu₂(μ-dicl)₄(CH₃OH)₂] (1), bis­{2-[2-(2,6-di­chloro­anilino)phen­yl]acetato-κ²O,O′}bis­(1-vinyl-1H-imidazole-κN³)copper(II), [Cu(dicl)₂(vim)₂] (2), and bis­{2-[2-(2,6-di­chloro­anilino)phen­yl]acetato-κ²O,O′}bis­(1H-imidazole-κN³)copper(II), [Cu(dicl)₂(im)₂] (3) [dicl is diclofenac (C₁₄H₁₀Cl₂NO₂), vim is 1-vinyl­imidazole (C₅H₆N₂) and im is imidazole (C₃H₄N₂)], have been synthesized and char­ac­ter­ized by elemental analysis, FT–IR spectroscopy, thermal analysis and single-crystal X-ray diffraction. X-ray diffraction analysis shows that complex 1 consists of dimeric units in which the dicl ligand exhibits a bidentate syn,syn-μ₂ coordination mode linking two copper(II) centres. Complexes 2 and 3 have mononuclear units with the general formula [Cu(dicl)₂L₂] (L is vim or im) in which the Cu^II ions are octa­hedrally coordinated by two L and two dicl chelating ligands. The L and dicl ligands both occupy the trans positions of the coordination octa­hedron. The different coordination modes of dicl in the title complexes were revealed by Fourier transform IR (FT–IR) spectroscopy. The spin matching between the copper(II) centres in the dimeric [Cu₂(μ-dicl)₄(CH₃OH)₂] units was also confirmed by magnetic data to be lower than the spin-only value and electron paramagnetic resonance (EPR) spectra. The thermal properties of the complexes were investigated by thermogravimetric (TG) and differential thermal analysis (DTA) techniques.

Computing details

For all structures, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (1); SHELXT (Sheldrick, 2015b) for (2), (3). Program(s) used to refine structure: SHELXL (Sheldrick, 2015b) for (1); SHELXL (Sheldrick, 2015a) for (2), (3). For all structures, molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Tetrakis{µ-2-[2-(2,6-dichloroanilino)phenyl]acetato-κ²O:O'}bis(methanol-κO)copper(II) (1)

Crystal data

[Cu2(C14H10Cl2NO2)4(CH4O)2]	Z = 1
Mr = 1371.68	F(000) = 698
Triclinic, P1	Dx = 1.534 Mg m^−3
a = 10.5258 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9908 (6) Å	Cell parameters from 18832 reflections
c = 13.0098 (7) Å	θ = 1.7–27.6°
α = 113.097 (4)°	µ = 1.14 mm^−1
β = 90.217 (4)°	T = 296 K
γ = 99.529 (4)°	Prism, blue
V = 1485.26 (14) Å^3	0.62 × 0.48 × 0.24 mm

Data collection

Stoe IPDS 2 diffractometer	6511 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	5112 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.049
Detector resolution: 6.67 pixels mm^-1	θmax = 27.0°, θmin = 1.7°
rotation method scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→15
Tmin = 0.523, Tmax = 0.799	l = −16→16
17101 measured reflections

Refinement

Refinement on F^2	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0514P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.002
6511 reflections	Δρmax = 0.37 e Å^−3
381 parameters	Δρmin = −0.31 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Cu1	0.62472 (2)	0.52584 (2)	1.00611 (2)	0.03371 (8)
Cl4	0.83375 (8)	−0.08701 (8)	0.89976 (7)	0.0768 (2)
Cl3	0.85861 (10)	0.30347 (8)	0.78876 (8)	0.0866 (3)
Cl2	0.16436 (11)	0.59749 (10)	0.76281 (7)	0.0937 (3)
Cl1	0.35861 (10)	0.36461 (9)	0.36844 (8)	0.0894 (3)
O4	0.62230 (15)	0.36876 (14)	1.01926 (13)	0.0455 (4)
O3	0.40678 (15)	0.32667 (14)	1.01186 (14)	0.0489 (4)
O2	0.60524 (15)	0.43459 (15)	0.84294 (12)	0.0470 (4)
O1	0.38967 (15)	0.39115 (15)	0.83091 (12)	0.0483 (4)
O5	0.83487 (16)	0.5793 (2)	1.01673 (17)	0.0632 (5)
N2	0.73925 (19)	0.1329 (2)	0.89084 (18)	0.0531 (5)
C14	0.4971 (2)	0.3826 (2)	0.79014 (17)	0.0396 (5)
C15	0.5167 (2)	0.30170 (19)	1.01925 (16)	0.0378 (4)
N1	0.3130 (2)	0.4168 (2)	0.6095 (2)	0.0598 (6)
C17	0.5110 (2)	0.07874 (19)	0.90659 (18)	0.0372 (4)
C16	0.5230 (2)	0.1793 (2)	1.02367 (18)	0.0411 (5)
H16A	0.453754	0.159035	1.065835	0.049*
H16B	0.604480	0.184519	1.061892	0.049*
C23	0.8557 (2)	0.1087 (2)	0.84249 (19)	0.0456 (5)
C22	0.6184 (2)	0.0558 (2)	0.84408 (18)	0.0404 (5)
C12	0.3755 (2)	0.2299 (2)	0.60337 (17)	0.0449 (5)
C18	0.3916 (2)	0.0066 (2)	0.8594 (2)	0.0459 (5)
H18	0.318817	0.022334	0.899259	0.055*
C7	0.2868 (2)	0.2867 (2)	0.57186 (18)	0.0465 (5)
C13	0.5015 (2)	0.3034 (2)	0.66690 (18)	0.0512 (6)
H13A	0.538808	0.356621	0.630494	0.061*
H13B	0.559761	0.246567	0.660437	0.061*
C28	0.9269 (2)	0.1854 (2)	0.7973 (2)	0.0504 (5)
C19	0.3787 (2)	−0.0882 (2)	0.7544 (2)	0.0530 (6)
H19	0.297905	−0.135746	0.724102	0.064*
C5	0.1809 (3)	0.5699 (3)	0.6232 (2)	0.0587 (6)
C6	0.2517 (2)	0.4810 (2)	0.5613 (2)	0.0529 (6)
C21	0.6051 (2)	−0.0404 (2)	0.7394 (2)	0.0515 (6)
H21	0.677187	−0.056897	0.698858	0.062*
C26	1.1011 (2)	0.0759 (3)	0.7665 (2)	0.0648 (8)
H26	1.183182	0.065756	0.742638	0.078*
C8	0.1751 (3)	0.2163 (3)	0.5065 (2)	0.0578 (6)
H8	0.116684	0.254285	0.484193	0.069*
C11	0.3481 (3)	0.1035 (2)	0.5707 (2)	0.0592 (7)
H11	0.406241	0.064457	0.591920	0.071*
C24	0.9129 (2)	0.0131 (2)	0.8444 (2)	0.0509 (6)
C25	1.0338 (3)	−0.0035 (3)	0.8074 (2)	0.0631 (7)
H25	1.069356	−0.068278	0.810327	0.076*
C20	0.4853 (2)	−0.1121 (2)	0.6949 (2)	0.0539 (6)
H20	0.477039	−0.176626	0.624557	0.065*
C10	0.2349 (3)	0.0339 (3)	0.5067 (2)	0.0701 (9)
H10	0.217088	−0.050950	0.485963	0.084*
C9	0.1501 (3)	0.0903 (3)	0.4743 (2)	0.0672 (8)
H9	0.075018	0.043575	0.430226	0.081*
C4	0.1240 (3)	0.6380 (3)	0.5780 (3)	0.0665 (7)
H4	0.077215	0.696516	0.622045	0.080*
C2	0.2059 (3)	0.5318 (3)	0.4029 (3)	0.0672 (7)
H2A	0.213237	0.517511	0.327771	0.081*
C27	1.0482 (2)	0.1701 (3)	0.7604 (2)	0.0598 (7)
H27	1.093533	0.223500	0.731672	0.072*
C1	0.2645 (3)	0.4657 (3)	0.4498 (2)	0.0588 (6)
C3	0.1369 (3)	0.6188 (3)	0.4680 (3)	0.0708 (8)
H3	0.098957	0.664478	0.437115	0.085*
C29	0.8947 (3)	0.6347 (4)	0.9482 (3)	0.0878 (11)
H29A	0.986590	0.651599	0.964286	0.132*
H29B	0.873667	0.580021	0.870947	0.132*
H29C	0.864663	0.710374	0.962341	0.132*
H5	0.8831 (14)	0.547 (3)	1.043 (3)	0.132*
H2	0.736 (3)	0.2071 (16)	0.916 (2)	0.052 (8)*
H1	0.331 (3)	0.454 (3)	0.6791 (15)	0.077 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.03398 (13)	0.03066 (14)	0.03555 (13)	0.00819 (9)	0.00045 (9)	0.01130 (9)
Cl4	0.0804 (5)	0.0800 (5)	0.0909 (5)	0.0253 (4)	0.0235 (4)	0.0519 (4)
Cl3	0.1045 (6)	0.0685 (5)	0.1028 (6)	0.0282 (5)	0.0185 (5)	0.0461 (5)
Cl2	0.1157 (7)	0.1037 (7)	0.0583 (4)	0.0344 (6)	0.0115 (4)	0.0229 (4)
Cl1	0.1132 (7)	0.0830 (6)	0.0783 (5)	0.0383 (5)	0.0316 (5)	0.0307 (4)
O4	0.0436 (8)	0.0412 (9)	0.0582 (9)	0.0112 (7)	0.0043 (7)	0.0254 (7)
O3	0.0452 (9)	0.0382 (9)	0.0683 (10)	0.0124 (7)	0.0058 (7)	0.0246 (8)
O2	0.0437 (8)	0.0525 (10)	0.0386 (8)	0.0105 (7)	−0.0010 (6)	0.0109 (7)
O1	0.0447 (8)	0.0552 (10)	0.0356 (7)	0.0105 (7)	0.0000 (6)	0.0076 (7)
O5	0.0385 (9)	0.0749 (13)	0.0740 (12)	0.0005 (8)	−0.0022 (8)	0.0313 (10)
N2	0.0361 (10)	0.0439 (12)	0.0644 (13)	0.0075 (9)	0.0095 (9)	0.0057 (10)
C14	0.0476 (12)	0.0379 (11)	0.0350 (10)	0.0125 (9)	0.0000 (9)	0.0145 (9)
C15	0.0480 (12)	0.0335 (11)	0.0345 (10)	0.0139 (9)	0.0059 (8)	0.0138 (8)
N1	0.0709 (14)	0.0472 (13)	0.0554 (13)	0.0080 (10)	−0.0193 (11)	0.0153 (10)
C17	0.0393 (10)	0.0313 (11)	0.0477 (11)	0.0117 (8)	0.0046 (8)	0.0208 (9)
C16	0.0487 (12)	0.0379 (12)	0.0449 (11)	0.0146 (9)	0.0098 (9)	0.0224 (9)
C23	0.0335 (10)	0.0512 (14)	0.0456 (12)	0.0073 (9)	0.0025 (9)	0.0126 (10)
C22	0.0353 (10)	0.0394 (12)	0.0490 (12)	0.0107 (8)	0.0048 (9)	0.0186 (9)
C12	0.0544 (13)	0.0484 (14)	0.0293 (10)	0.0114 (10)	0.0067 (9)	0.0120 (9)
C18	0.0370 (11)	0.0439 (13)	0.0615 (14)	0.0111 (9)	0.0069 (10)	0.0245 (11)
C7	0.0509 (13)	0.0460 (13)	0.0364 (11)	0.0026 (10)	0.0003 (9)	0.0123 (9)
C13	0.0507 (13)	0.0593 (15)	0.0365 (11)	0.0160 (11)	0.0016 (9)	0.0092 (10)
C28	0.0482 (13)	0.0500 (14)	0.0471 (12)	0.0042 (10)	0.0011 (10)	0.0149 (10)
C19	0.0419 (12)	0.0467 (14)	0.0656 (15)	0.0043 (10)	−0.0077 (11)	0.0189 (12)
C5	0.0548 (14)	0.0571 (16)	0.0571 (15)	0.0049 (12)	−0.0042 (11)	0.0172 (12)
C6	0.0513 (13)	0.0453 (14)	0.0575 (14)	0.0023 (10)	−0.0104 (11)	0.0183 (11)
C21	0.0488 (13)	0.0506 (14)	0.0505 (13)	0.0149 (11)	0.0098 (10)	0.0128 (11)
C26	0.0381 (12)	0.101 (2)	0.0523 (14)	0.0188 (14)	0.0104 (11)	0.0254 (15)
C8	0.0516 (14)	0.0666 (17)	0.0464 (13)	0.0000 (12)	−0.0052 (10)	0.0176 (12)
C11	0.0881 (19)	0.0490 (15)	0.0388 (12)	0.0160 (13)	0.0077 (12)	0.0142 (10)
C24	0.0475 (12)	0.0590 (15)	0.0493 (13)	0.0159 (11)	0.0077 (10)	0.0225 (11)
C25	0.0524 (14)	0.086 (2)	0.0571 (15)	0.0340 (14)	0.0074 (12)	0.0262 (14)
C20	0.0578 (14)	0.0459 (14)	0.0488 (13)	0.0129 (11)	−0.0042 (11)	0.0078 (11)
C10	0.105 (2)	0.0441 (15)	0.0469 (14)	−0.0068 (15)	0.0107 (15)	0.0107 (12)
C9	0.0717 (18)	0.0671 (19)	0.0435 (13)	−0.0172 (15)	−0.0014 (12)	0.0133 (13)
C4	0.0573 (16)	0.0557 (17)	0.081 (2)	0.0137 (13)	−0.0056 (14)	0.0207 (14)
C2	0.0735 (18)	0.0695 (19)	0.0615 (16)	0.0029 (15)	−0.0080 (14)	0.0332 (14)
C27	0.0485 (13)	0.0768 (19)	0.0476 (13)	−0.0029 (13)	0.0061 (11)	0.0235 (13)
C1	0.0620 (16)	0.0539 (16)	0.0586 (15)	0.0072 (12)	0.0007 (12)	0.0215 (12)
C3	0.0716 (19)	0.068 (2)	0.082 (2)	0.0105 (15)	−0.0123 (16)	0.0405 (16)
C29	0.076 (2)	0.091 (3)	0.078 (2)	−0.0196 (18)	0.0110 (17)	0.0284 (18)

Geometric parameters (Å, º)

Cu1—O3^i	1.9519 (16)	C18—H18	0.9300
Cu1—O4	1.9532 (15)	C7—C8	1.385 (3)
Cu1—O2	1.9610 (15)	C13—H13A	0.9700
Cu1—O1^i	1.9764 (15)	C13—H13B	0.9700
Cu1—O5	2.1866 (17)	C28—C27	1.380 (4)
Cu1—Cu1^i	2.5854 (5)	C19—C20	1.371 (4)
Cl4—C24	1.734 (3)	C19—H19	0.9300
Cl3—C28	1.729 (3)	C5—C4	1.381 (4)
Cl2—C5	1.729 (3)	C5—C6	1.390 (4)
Cl1—C1	1.723 (3)	C6—C1	1.399 (4)
O4—C15	1.260 (3)	C21—C20	1.381 (4)
O3—C15	1.254 (3)	C21—H21	0.9300
O2—C14	1.256 (3)	C26—C25	1.366 (4)
O1—C14	1.254 (3)	C26—C27	1.368 (4)
O5—C29	1.401 (4)	C26—H26	0.9300
O5—H5	0.829 (9)	C8—C9	1.378 (4)
N2—C23	1.401 (3)	C8—H8	0.9300
N2—C22	1.417 (3)	C11—C10	1.388 (4)
N2—H2	0.824 (17)	C11—H11	0.9300
C14—C13	1.515 (3)	C24—C25	1.380 (3)
C15—C16	1.503 (3)	C25—H25	0.9300
N1—C6	1.393 (3)	C20—H20	0.9300
N1—C7	1.417 (3)	C10—C9	1.360 (5)
N1—H1	0.842 (17)	C10—H10	0.9300
C17—C18	1.387 (3)	C9—H9	0.9300
C17—C22	1.396 (3)	C4—C3	1.369 (4)
C17—C16	1.516 (3)	C4—H4	0.9300
C16—H16A	0.9700	C2—C3	1.376 (4)
C16—H16B	0.9700	C2—C1	1.386 (4)
C23—C24	1.388 (3)	C2—H2A	0.9300
C23—C28	1.398 (3)	C27—H27	0.9300
C22—C21	1.385 (3)	C3—H3	0.9300
C12—C11	1.383 (4)	C29—H29A	0.9600
C12—C7	1.389 (3)	C29—H29B	0.9600
C12—C13	1.501 (3)	C29—H29C	0.9600
C18—C19	1.381 (3)
O3^i—Cu1—O4	169.60 (6)	C14—C13—H13B	108.1
O3^i—Cu1—O2	90.02 (7)	H13A—C13—H13B	107.3
O4—Cu1—O2	87.92 (7)	C27—C28—C23	122.4 (2)
O3^i—Cu1—O1^i	89.46 (7)	C27—C28—Cl3	119.8 (2)
O4—Cu1—O1^i	90.76 (7)	C23—C28—Cl3	117.78 (19)
O2—Cu1—O1^i	169.70 (6)	C20—C19—C18	119.9 (2)
O3^i—Cu1—O5	93.77 (7)	C20—C19—H19	120.1
O4—Cu1—O5	96.57 (7)	C18—C19—H19	120.1
O2—Cu1—O5	95.55 (7)	C4—C5—C6	122.7 (3)
O1^i—Cu1—O5	94.74 (7)	C4—C5—Cl2	118.5 (2)
O3^i—Cu1—Cu1^i	83.20 (5)	C6—C5—Cl2	118.8 (2)
O4—Cu1—Cu1^i	86.46 (5)	C5—C6—N1	121.9 (2)
O2—Cu1—Cu1^i	84.89 (5)	C5—C6—C1	116.0 (2)
O1^i—Cu1—Cu1^i	84.84 (5)	N1—C6—C1	122.0 (3)
O5—Cu1—Cu1^i	176.95 (6)	C20—C21—C22	120.4 (2)
C15—O4—Cu1	120.47 (14)	C20—C21—H21	119.8
C15—O3—Cu1^i	124.41 (15)	C22—C21—H21	119.8
C14—O2—Cu1	122.47 (14)	C25—C26—C27	120.3 (2)
C14—O1—Cu1^i	121.76 (13)	C25—C26—H26	119.9
C29—O5—Cu1	121.02 (19)	C27—C26—H26	119.9
C29—O5—H5	114.2 (12)	C9—C8—C7	120.4 (3)
Cu1—O5—H5	121.4 (12)	C9—C8—H8	119.8
C23—N2—C22	122.94 (19)	C7—C8—H8	119.8
C23—N2—H2	111.7 (19)	C12—C11—C10	120.9 (3)
C22—N2—H2	113.6 (19)	C12—C11—H11	119.5
O1—C14—O2	125.66 (19)	C10—C11—H11	119.5
O1—C14—C13	119.10 (19)	C25—C24—C23	122.6 (2)
O2—C14—C13	115.24 (19)	C25—C24—Cl4	117.8 (2)
O3—C15—O4	125.4 (2)	C23—C24—Cl4	119.54 (18)
O3—C15—C16	117.42 (19)	C26—C25—C24	119.6 (3)
O4—C15—C16	117.11 (19)	C26—C25—H25	120.2
C6—N1—C7	123.4 (2)	C24—C25—H25	120.2
C6—N1—H1	115 (2)	C19—C20—C21	120.0 (2)
C7—N1—H1	113 (2)	C19—C20—H20	120.0
C18—C17—C22	118.5 (2)	C21—C20—H20	120.0
C18—C17—C16	120.05 (19)	C9—C10—C11	119.8 (3)
C22—C17—C16	121.48 (19)	C9—C10—H10	120.1
C15—C16—C17	110.75 (17)	C11—C10—H10	120.1
C15—C16—H16A	109.5	C10—C9—C8	120.2 (3)
C17—C16—H16A	109.5	C10—C9—H9	119.9
C15—C16—H16B	109.5	C8—C9—H9	119.9
C17—C16—H16B	109.5	C3—C4—C5	119.6 (3)
H16A—C16—H16B	108.1	C3—C4—H4	120.2
C24—C23—C28	115.6 (2)	C5—C4—H4	120.2
C24—C23—N2	122.3 (2)	C3—C2—C1	119.8 (3)
C28—C23—N2	121.9 (2)	C3—C2—H2A	120.1
C21—C22—C17	120.0 (2)	C1—C2—H2A	120.1
C21—C22—N2	121.8 (2)	C26—C27—C28	119.5 (3)
C17—C22—N2	118.24 (19)	C26—C27—H27	120.3
C11—C12—C7	118.7 (2)	C28—C27—H27	120.3
C11—C12—C13	120.5 (2)	C2—C1—C6	121.8 (3)
C7—C12—C13	120.7 (2)	C2—C1—Cl1	118.6 (2)
C19—C18—C17	121.2 (2)	C6—C1—Cl1	119.6 (2)
C19—C18—H18	119.4	C4—C3—C2	120.0 (3)
C17—C18—H18	119.4	C4—C3—H3	120.0
C8—C7—C12	120.0 (2)	C2—C3—H3	120.0
C8—C7—N1	121.6 (2)	O5—C29—H29A	109.5
C12—C7—N1	118.4 (2)	O5—C29—H29B	109.5
C12—C13—C14	116.90 (19)	H29A—C29—H29B	109.5
C12—C13—H13A	108.1	O5—C29—H29C	109.5
C14—C13—H13A	108.1	H29A—C29—H29C	109.5
C12—C13—H13B	108.1	H29B—C29—H29C	109.5
Cu1^i—O1—C14—O2	−7.9 (3)	C4—C5—C6—N1	177.3 (3)
Cu1^i—O1—C14—C13	171.88 (16)	Cl2—C5—C6—N1	−2.2 (4)
Cu1—O2—C14—O1	7.0 (3)	C4—C5—C6—C1	1.2 (4)
Cu1—O2—C14—C13	−172.79 (16)	Cl2—C5—C6—C1	−178.2 (2)
Cu1^i—O3—C15—O4	2.0 (3)	C7—N1—C6—C5	121.3 (3)
Cu1^i—O3—C15—C16	−175.29 (13)	C7—N1—C6—C1	−62.9 (4)
Cu1—O4—C15—O3	−0.4 (3)	C17—C22—C21—C20	1.8 (4)
Cu1—O4—C15—C16	176.91 (13)	N2—C22—C21—C20	−178.4 (2)
O3—C15—C16—C17	84.8 (2)	C12—C7—C8—C9	1.3 (4)
O4—C15—C16—C17	−92.8 (2)	N1—C7—C8—C9	−177.8 (2)
C18—C17—C16—C15	−95.1 (2)	C7—C12—C11—C10	0.7 (4)
C22—C17—C16—C15	85.2 (2)	C13—C12—C11—C10	−176.5 (2)
C22—N2—C23—C24	−71.7 (3)	C28—C23—C24—C25	1.9 (4)
C22—N2—C23—C28	113.5 (3)	N2—C23—C24—C25	−173.1 (2)
C18—C17—C22—C21	−2.6 (3)	C28—C23—C24—Cl4	179.45 (17)
C16—C17—C22—C21	177.0 (2)	N2—C23—C24—Cl4	4.4 (3)
C18—C17—C22—N2	177.5 (2)	C27—C26—C25—C24	−1.0 (4)
C16—C17—C22—N2	−2.8 (3)	C23—C24—C25—C26	−0.4 (4)
C23—N2—C22—C21	−8.4 (4)	Cl4—C24—C25—C26	−177.9 (2)
C23—N2—C22—C17	171.4 (2)	C18—C19—C20—C21	−0.8 (4)
C22—C17—C18—C19	1.8 (3)	C22—C21—C20—C19	0.0 (4)
C16—C17—C18—C19	−177.9 (2)	C12—C11—C10—C9	0.7 (4)
C11—C12—C7—C8	−1.7 (3)	C11—C10—C9—C8	−1.2 (4)
C13—C12—C7—C8	175.4 (2)	C7—C8—C9—C10	0.1 (4)
C11—C12—C7—N1	177.5 (2)	C6—C5—C4—C3	−0.1 (4)
C13—C12—C7—N1	−5.4 (3)	Cl2—C5—C4—C3	179.3 (2)
C6—N1—C7—C8	−18.3 (4)	C25—C26—C27—C28	0.8 (4)
C6—N1—C7—C12	162.5 (2)	C23—C28—C27—C26	0.9 (4)
C11—C12—C13—C14	−107.3 (3)	Cl3—C28—C27—C26	−179.4 (2)
C7—C12—C13—C14	75.6 (3)	C3—C2—C1—C6	2.5 (5)
O1—C14—C13—C12	−5.7 (3)	C3—C2—C1—Cl1	−176.0 (2)
O2—C14—C13—C12	174.2 (2)	C5—C6—C1—C2	−2.4 (4)
C24—C23—C28—C27	−2.2 (3)	N1—C6—C1—C2	−178.4 (3)
N2—C23—C28—C27	172.9 (2)	C5—C6—C1—Cl1	176.1 (2)
C24—C23—C28—Cl3	178.11 (18)	N1—C6—C1—Cl1	0.0 (4)
N2—C23—C28—Cl3	−6.8 (3)	C5—C4—C3—C2	0.2 (5)
C17—C18—C19—C20	−0.1 (4)	C1—C2—C3—C4	−1.3 (5)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29A···Cl2^ii	0.96	3.15	3.701 (3)	119
N2—H2···O4	0.82 (2)	2.40 (2)	3.125 (3)	148 (2)
N1—H1···O1	0.84 (2)	2.48 (3)	3.132 (3)	135 (3)

Symmetry code: (ii) x+1, y, z.

Bis{2-[2-(2,6-dichloroanilino)phenyl]acetato-κ²O,O'}bis(1-vinyl-1H-imidazole-κN³)copper(II) (2)

Crystal data

[Cu(C14H10Cl2NO2)2(C5H6N2)2]	F(000) = 862
Mr = 842.03	Dx = 1.441 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.1741 (7) Å	Cell parameters from 12318 reflections
b = 7.9241 (2) Å	θ = 1.7–27.1°
c = 16.3037 (8) Å	µ = 0.89 mm^−1
β = 98.073 (4)°	T = 296 K
V = 1940.95 (14) Å^3	Prism, blue
Z = 2	0.37 × 0.28 × 0.17 mm

Data collection

Stoe IPDS 2 diffractometer	3803 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2650 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.037
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.5°
rotation method scans	h = −18→18
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.740, Tmax = 0.876	l = −20→20
12278 measured reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.171	w = 1/[σ^2(Fo^2) + (0.1109P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3803 reflections	Δρmax = 1.06 e Å^−3
241 parameters	Δρmin = −0.60 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Cu1	0.500000	0.500000	0.500000	0.0522 (2)
Cl1	0.07722 (9)	1.00235 (15)	0.41883 (10)	0.0884 (4)
Cl2	0.21990 (10)	0.38030 (16)	0.43961 (10)	0.1029 (5)
O1	0.40382 (15)	0.6691 (3)	0.48896 (15)	0.0590 (6)
O2	0.51228 (16)	0.8041 (4)	0.56651 (16)	0.0728 (8)
N1	0.21950 (18)	0.7502 (4)	0.47099 (18)	0.0575 (7)
H1	0.267206	0.746993	0.448111	0.069*
N2	0.4652 (2)	0.4225 (4)	0.60695 (18)	0.0600 (8)
N3	0.3973 (3)	0.4041 (5)	0.7157 (2)	0.0832 (11)
C12	0.2980 (2)	0.9128 (5)	0.5830 (2)	0.0562 (8)
C7	0.2238 (2)	0.8204 (4)	0.5506 (2)	0.0518 (8)
C14	0.4354 (2)	0.8003 (5)	0.5302 (2)	0.0564 (9)
C6	0.1412 (2)	0.6857 (5)	0.4276 (2)	0.0572 (9)
C13	0.3731 (3)	0.9477 (5)	0.5322 (3)	0.0649 (10)
H13A	0.347558	0.975729	0.475980	0.078*
H13B	0.406725	1.044756	0.555424	0.078*
C1	0.0683 (2)	0.7884 (5)	0.4005 (3)	0.0663 (10)
C8	0.1548 (2)	0.7984 (5)	0.5978 (2)	0.0614 (9)
H8	0.104335	0.737715	0.576221	0.074*
C11	0.3030 (3)	0.9775 (5)	0.6618 (3)	0.0736 (11)
H11	0.353264	1.037670	0.684312	0.088*
C15	0.3926 (3)	0.4632 (5)	0.6379 (3)	0.0705 (11)
H15	0.345074	0.523923	0.610074	0.085*
C17	0.5169 (3)	0.3344 (7)	0.6679 (2)	0.0799 (13)
H17	0.572893	0.290833	0.663284	0.096*
C9	0.1608 (3)	0.8656 (6)	0.6758 (3)	0.0764 (12)
H9	0.114400	0.850207	0.706679	0.092*
C5	0.1319 (3)	0.5149 (5)	0.4065 (3)	0.0696 (10)
C2	−0.0084 (3)	0.7249 (7)	0.3561 (3)	0.0866 (14)
H2	−0.056662	0.795582	0.339791	0.104*
C16	0.4759 (4)	0.3193 (8)	0.7351 (3)	0.0927 (14)
H16	0.496489	0.263465	0.784243	0.111*
C3	−0.0132 (4)	0.5551 (8)	0.3358 (4)	0.0971 (17)
H3	−0.064688	0.512152	0.305226	0.117*
C4	0.0565 (4)	0.4508 (7)	0.3603 (3)	0.0907 (15)
H4	0.053243	0.337169	0.346020	0.109*
C10	0.2337 (3)	0.9541 (7)	0.7084 (3)	0.0834 (13)
H10	0.237464	0.998998	0.761447	0.100*
C18	0.3407 (4)	0.4116 (9)	0.7772 (4)	0.1093 (19)
H18	0.357568	0.360491	0.828386	0.131*
C19	0.2648 (6)	0.4901 (10)	0.7624 (6)	0.148 (3)
H19A	0.247880	0.541187	0.711285	0.178*
H19B	0.227436	0.495094	0.802978	0.178*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0397 (3)	0.0731 (4)	0.0447 (3)	0.0038 (3)	0.0091 (2)	−0.0047 (3)
Cl1	0.0769 (7)	0.0682 (7)	0.1199 (10)	0.0141 (5)	0.0127 (7)	0.0139 (6)
Cl2	0.1121 (10)	0.0646 (7)	0.1226 (11)	0.0153 (7)	−0.0160 (8)	−0.0044 (7)
O1	0.0446 (12)	0.0736 (17)	0.0590 (14)	0.0022 (11)	0.0081 (10)	−0.0084 (13)
O2	0.0480 (14)	0.105 (2)	0.0650 (15)	−0.0126 (14)	0.0061 (12)	−0.0039 (15)
N1	0.0443 (14)	0.0676 (19)	0.0624 (17)	−0.0042 (14)	0.0131 (12)	−0.0056 (15)
N2	0.0539 (16)	0.077 (2)	0.0514 (16)	0.0054 (15)	0.0154 (13)	−0.0019 (16)
N3	0.105 (3)	0.088 (3)	0.067 (2)	−0.027 (2)	0.047 (2)	−0.0161 (19)
C12	0.0499 (18)	0.049 (2)	0.072 (2)	0.0024 (15)	0.0153 (16)	−0.0083 (18)
C7	0.0455 (17)	0.0485 (18)	0.063 (2)	0.0039 (14)	0.0140 (14)	0.0021 (16)
C14	0.0478 (18)	0.073 (2)	0.0515 (18)	−0.0068 (17)	0.0186 (15)	0.0012 (18)
C6	0.0511 (19)	0.064 (2)	0.057 (2)	−0.0052 (16)	0.0085 (15)	0.0030 (18)
C13	0.056 (2)	0.058 (2)	0.085 (3)	−0.0103 (17)	0.0237 (19)	−0.0003 (19)
C1	0.053 (2)	0.069 (2)	0.077 (2)	−0.0015 (18)	0.0092 (18)	0.013 (2)
C8	0.0510 (19)	0.067 (2)	0.069 (2)	0.0014 (17)	0.0187 (16)	0.0022 (19)
C11	0.068 (2)	0.070 (3)	0.085 (3)	−0.0048 (19)	0.016 (2)	−0.017 (2)
C15	0.071 (2)	0.073 (3)	0.071 (2)	−0.002 (2)	0.026 (2)	−0.005 (2)
C17	0.072 (3)	0.116 (4)	0.051 (2)	0.003 (3)	0.0055 (18)	0.007 (2)
C9	0.064 (2)	0.095 (3)	0.075 (3)	0.004 (2)	0.027 (2)	0.001 (2)
C5	0.076 (3)	0.061 (2)	0.068 (2)	−0.0087 (19)	0.0003 (19)	0.006 (2)
C2	0.059 (2)	0.097 (4)	0.100 (3)	−0.008 (2)	−0.003 (2)	0.029 (3)
C16	0.106 (3)	0.121 (4)	0.052 (2)	−0.011 (3)	0.014 (2)	0.002 (3)
C3	0.079 (3)	0.109 (4)	0.095 (4)	−0.029 (3)	−0.019 (3)	0.022 (3)
C4	0.106 (4)	0.075 (3)	0.086 (3)	−0.026 (3)	−0.006 (3)	0.006 (3)
C10	0.085 (3)	0.099 (3)	0.070 (3)	0.007 (3)	0.023 (2)	−0.023 (2)
C18	0.115 (5)	0.125 (5)	0.097 (4)	−0.008 (4)	0.047 (4)	−0.011 (4)
C19	0.135 (7)	0.174 (8)	0.136 (7)	0.019 (6)	0.018 (5)	0.022 (5)

Geometric parameters (Å, º)

Cu1—O1	1.971 (2)	C13—H13A	0.9700
Cu1—O1^i	1.971 (2)	C13—H13B	0.9700
Cu1—N2	1.989 (3)	C1—C2	1.377 (6)
Cu1—N2^i	1.989 (3)	C8—C9	1.369 (6)
Cu1—O2	2.639 (1)	C8—H8	0.9300
Cu1—O2^i	2.6385 (1)	C11—C10	1.393 (7)
Cl1—C1	1.724 (5)	C11—H11	0.9300
Cl2—C5	1.735 (5)	C15—H15	0.9300
O1—C14	1.294 (5)	C17—C16	1.338 (6)
O2—C14	1.232 (4)	C17—H17	0.9300
N1—C6	1.392 (4)	C9—C10	1.353 (7)
N1—C7	1.405 (4)	C9—H9	0.9300
N1—H1	0.8600	C5—C4	1.376 (7)
N2—C15	1.314 (5)	C2—C3	1.385 (8)
N2—C17	1.368 (5)	C2—H2	0.9300
N3—C15	1.345 (6)	C16—H16	0.9300
N3—C16	1.367 (7)	C3—C4	1.357 (8)
N3—C18	1.412 (6)	C3—H3	0.9300
C12—C11	1.376 (6)	C4—H4	0.9300
C12—C7	1.384 (5)	C10—H10	0.9300
C12—C13	1.524 (5)	C18—C19	1.301 (7)
C7—C8	1.395 (5)	C18—H18	0.9300
C14—C13	1.506 (5)	C19—H19A	0.9300
C6—C1	1.394 (5)	C19—H19B	0.9300
C6—C5	1.399 (6)
O1—Cu1—O1^i	180.0	C9—C8—C7	120.4 (4)
O1—Cu1—N2	90.31 (12)	C9—C8—H8	119.8
O1—Cu1—O2	54.92 (12)	C7—C8—H8	119.8
O2—Cu1—N2	86.21 (12)	C12—C11—C10	120.8 (4)
O1^i—Cu1—N2	89.69 (11)	C12—C11—H11	119.6
O1^i—Cu1—O2	125.08 (11)	C10—C11—H11	119.6
O1—Cu1—N2^i	89.69 (11)	N2—C15—N3	109.9 (4)
O1^i—Cu1—N2^i	90.31 (12)	N2—C15—H15	125.1
N2—Cu1—N2^i	180.00 (19)	N3—C15—H15	125.1
C14—O1—Cu1	106.5 (2)	C16—C17—N2	110.8 (4)
C6—N1—C7	122.7 (3)	C16—C17—H17	124.6
C6—N1—H1	118.7	N2—C17—H17	124.6
C7—N1—H1	118.7	C10—C9—C8	120.7 (4)
C15—N2—C17	105.8 (3)	C10—C9—H9	119.6
C15—N2—Cu1	126.9 (3)	C8—C9—H9	119.6
C17—N2—Cu1	126.8 (3)	C4—C5—C6	122.6 (5)
C15—N3—C16	108.6 (4)	C4—C5—Cl2	119.2 (4)
C15—N3—C18	134.4 (5)	C6—C5—Cl2	118.2 (3)
C16—N3—C18	117.0 (5)	C1—C2—C3	119.5 (5)
C11—C12—C7	119.3 (3)	C1—C2—H2	120.3
C11—C12—C13	119.5 (4)	C3—C2—H2	120.3
C7—C12—C13	121.3 (3)	C17—C16—N3	104.9 (4)
C12—C7—C8	119.3 (3)	C17—C16—H16	127.6
C12—C7—N1	119.4 (3)	N3—C16—H16	127.6
C8—C7—N1	121.3 (3)	C4—C3—C2	120.6 (5)
O2—C14—O1	121.8 (4)	C4—C3—H3	119.7
O2—C14—C13	121.7 (4)	C2—C3—H3	119.7
O1—C14—C13	116.5 (3)	C3—C4—C5	119.4 (5)
N1—C6—C1	122.0 (4)	C3—C4—H4	120.3
N1—C6—C5	122.0 (4)	C5—C4—H4	120.3
C1—C6—C5	116.0 (4)	C9—C10—C11	119.5 (4)
C14—C13—C12	113.0 (3)	C9—C10—H10	120.2
C14—C13—H13A	109.0	C11—C10—H10	120.2
C12—C13—H13A	109.0	C19—C18—N3	120.0 (7)
C14—C13—H13B	109.0	C19—C18—H18	120.0
C12—C13—H13B	109.0	N3—C18—H18	120.0
H13A—C13—H13B	107.8	C18—C19—H19A	120.0
C2—C1—C6	121.9 (4)	C18—C19—H19B	120.0
C2—C1—Cl1	119.3 (4)	H19A—C19—H19B	120.0
C6—C1—Cl1	118.7 (3)
C11—C12—C7—C8	1.5 (6)	Cu1—N2—C15—N3	−172.2 (3)
C13—C12—C7—C8	−177.0 (3)	C16—N3—C15—N2	−0.9 (5)
C11—C12—C7—N1	−178.3 (4)	C18—N3—C15—N2	179.1 (5)
C13—C12—C7—N1	3.2 (5)	C15—N2—C17—C16	0.8 (6)
C6—N1—C7—C12	−166.7 (4)	Cu1—N2—C17—C16	173.1 (4)
C6—N1—C7—C8	13.4 (5)	C7—C8—C9—C10	−0.1 (7)
Cu1—O1—C14—O2	0.4 (4)	N1—C6—C5—C4	−176.9 (4)
Cu1—O1—C14—C13	−179.0 (2)	C1—C6—C5—C4	1.1 (6)
C7—N1—C6—C1	65.9 (5)	N1—C6—C5—Cl2	2.7 (5)
C7—N1—C6—C5	−116.2 (4)	C1—C6—C5—Cl2	−179.2 (3)
O2—C14—C13—C12	−110.0 (4)	C6—C1—C2—C3	−1.6 (7)
O1—C14—C13—C12	69.4 (5)	Cl1—C1—C2—C3	175.2 (4)
C11—C12—C13—C14	101.9 (4)	N2—C17—C16—N3	−1.3 (6)
C7—C12—C13—C14	−79.6 (5)	C15—N3—C16—C17	1.4 (6)
N1—C6—C1—C2	178.6 (4)	C18—N3—C16—C17	−178.7 (5)
C5—C6—C1—C2	0.6 (6)	C1—C2—C3—C4	0.9 (8)
N1—C6—C1—Cl1	1.8 (5)	C2—C3—C4—C5	0.8 (9)
C5—C6—C1—Cl1	−176.2 (3)	C6—C5—C4—C3	−1.8 (8)
C12—C7—C8—C9	−0.8 (6)	Cl2—C5—C4—C3	178.6 (4)
N1—C7—C8—C9	179.0 (4)	C8—C9—C10—C11	0.3 (8)
C7—C12—C11—C10	−1.4 (6)	C12—C11—C10—C9	0.5 (8)
C13—C12—C11—C10	177.2 (4)	C15—N3—C18—C19	0.1 (11)
C17—N2—C15—N3	0.1 (5)	C16—N3—C18—C19	−179.8 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.18	2.845 (4)	134
C16—H16···O2^ii	0.93	2.48	3.217 (5)	137
C4—H4···Cl1^iii	0.93	2.91	3.682 (5)	142
C18—H18···O2^ii	0.93	2.47	3.255 (8)	143

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

Bis{2-[2-(2,6-dichloroanilino)phenyl]acetato-κ²O,O'}bis(1H-imidazole-κN³)copper(II) (3)

Crystal data

[Cu(C14H10Cl2NO2)2(C3H4N2)2]	F(000) = 806
Mr = 789.96	Dx = 1.470 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.6526 (4) Å	Cell parameters from 12783 reflections
b = 7.5494 (5) Å	θ = 1.3–25.9°
c = 31.071 (2) Å	µ = 0.96 mm^−1
β = 96.277 (5)°	T = 296 K
V = 1784.30 (19) Å^3	Prism, purple
Z = 2	0.39 × 0.29 × 0.24 mm

Data collection

Stoe IPDS 2 diffractometer	3220 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2070 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.107
Detector resolution: 6.67 pixels mm^-1	θmax = 25.4°, θmin = 1.3°
rotation method scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→9
Tmin = 0.799, Tmax = 0.883	l = −37→37
10926 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.185	w = 1/[σ^2(Fo^2) + (0.1024P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3220 reflections	Δρmax = 0.37 e Å^−3
223 parameters	Δρmin = −0.75 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Cu1	0.500000	0.500000	0.500000	0.0550 (3)
Cl2	1.02616 (19)	0.5077 (2)	0.71892 (5)	0.0912 (5)
Cl1	0.39903 (19)	0.5993 (2)	0.62379 (7)	0.1116 (6)
O2	0.6983 (4)	0.5035 (4)	0.54546 (10)	0.0631 (8)
O1	0.8236 (4)	0.3301 (5)	0.49987 (11)	0.0726 (9)
N2	0.5843 (4)	0.7264 (5)	0.47819 (12)	0.0579 (9)
N1	0.7736 (5)	0.4806 (5)	0.63882 (12)	0.0585 (9)
H1	0.781194	0.548884	0.616946	0.070*
N3	0.6974 (5)	0.9915 (5)	0.47797 (15)	0.0676 (10)
H3	0.756100	1.084437	0.486592	0.081*
C7	0.8318 (5)	0.3037 (6)	0.63700 (14)	0.0548 (10)
C12	0.9300 (5)	0.2545 (6)	0.60321 (15)	0.0568 (11)
C8	0.7926 (6)	0.1775 (7)	0.66655 (15)	0.0650 (12)
H8	0.730687	0.210903	0.689373	0.078*
C14	0.8258 (6)	0.4059 (7)	0.53456 (15)	0.0625 (12)
C13	0.9795 (5)	0.3849 (7)	0.57013 (15)	0.0635 (12)
H13A	1.082685	0.343212	0.557618	0.076*
H13B	1.007275	0.498440	0.583810	0.076*
C6	0.7047 (6)	0.5473 (6)	0.67496 (16)	0.0607 (12)
C17	0.6833 (6)	0.8445 (7)	0.50064 (16)	0.0628 (11)
H17	0.736276	0.826961	0.528706	0.075*
C16	0.6031 (7)	0.9697 (7)	0.43888 (18)	0.0735 (14)
H16	0.588830	1.051711	0.416433	0.088*
C9	0.8423 (8)	0.0047 (7)	0.66325 (18)	0.0773 (14)
H9	0.813522	−0.077589	0.683594	0.093*
C15	0.5341 (6)	0.8054 (7)	0.43898 (16)	0.0683 (12)
H15	0.463653	0.753658	0.416096	0.082*
C11	0.9771 (7)	0.0779 (8)	0.60042 (18)	0.0751 (14)
H11	1.039489	0.042209	0.577871	0.090*
C5	0.8043 (7)	0.5670 (7)	0.71466 (17)	0.0721 (13)
C10	0.9341 (8)	−0.0474 (7)	0.6302 (2)	0.0835 (16)
H10	0.967305	−0.165104	0.627697	0.100*
C1	0.5347 (7)	0.6140 (7)	0.6728 (2)	0.0786 (15)
C4	0.7404 (9)	0.6360 (8)	0.7508 (2)	0.0924 (18)
H4	0.810587	0.639668	0.777182	0.111*
C2	0.4669 (8)	0.6918 (9)	0.7080 (3)	0.102 (2)
H2	0.353590	0.738120	0.705334	0.123*
C3	0.5730 (11)	0.6985 (10)	0.7473 (3)	0.116 (3)
H3A	0.528769	0.746315	0.771517	0.139*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0502 (4)	0.0567 (5)	0.0573 (4)	−0.0036 (4)	0.0024 (3)	−0.0003 (4)
Cl2	0.0846 (9)	0.0994 (11)	0.0849 (10)	0.0075 (8)	−0.0125 (7)	−0.0113 (8)
Cl1	0.0633 (8)	0.0947 (12)	0.1711 (17)	0.0110 (8)	−0.0133 (9)	−0.0066 (11)
O2	0.0573 (17)	0.072 (2)	0.0589 (17)	−0.0011 (17)	0.0010 (13)	0.0031 (15)
O1	0.081 (2)	0.072 (2)	0.065 (2)	−0.0185 (19)	0.0097 (16)	−0.0040 (18)
N2	0.0481 (18)	0.059 (2)	0.066 (2)	−0.0052 (17)	0.0072 (16)	−0.0004 (18)
N1	0.068 (2)	0.050 (2)	0.059 (2)	0.0025 (18)	0.0128 (17)	0.0048 (17)
N3	0.062 (2)	0.055 (2)	0.088 (3)	−0.009 (2)	0.022 (2)	−0.005 (2)
C7	0.046 (2)	0.055 (3)	0.063 (2)	−0.002 (2)	0.0034 (18)	0.003 (2)
C12	0.044 (2)	0.062 (3)	0.065 (3)	0.002 (2)	0.0066 (18)	0.001 (2)
C8	0.073 (3)	0.059 (3)	0.064 (3)	−0.005 (2)	0.012 (2)	0.002 (2)
C14	0.063 (3)	0.066 (3)	0.058 (3)	−0.017 (2)	0.006 (2)	0.008 (2)
C13	0.046 (2)	0.076 (3)	0.069 (3)	−0.002 (2)	0.009 (2)	0.004 (2)
C6	0.062 (3)	0.045 (2)	0.078 (3)	−0.004 (2)	0.019 (2)	−0.002 (2)
C17	0.057 (2)	0.063 (3)	0.071 (3)	−0.005 (2)	0.014 (2)	−0.005 (2)
C16	0.063 (3)	0.077 (4)	0.080 (3)	0.005 (3)	0.009 (2)	0.021 (3)
C9	0.104 (4)	0.053 (3)	0.073 (3)	−0.010 (3)	0.006 (3)	0.008 (3)
C15	0.061 (3)	0.072 (3)	0.074 (3)	−0.008 (3)	0.011 (2)	0.009 (3)
C11	0.065 (3)	0.080 (4)	0.081 (3)	0.015 (3)	0.013 (2)	−0.006 (3)
C5	0.080 (3)	0.065 (3)	0.073 (3)	−0.007 (3)	0.015 (3)	−0.008 (3)
C10	0.099 (4)	0.059 (3)	0.092 (4)	0.017 (3)	0.006 (3)	−0.002 (3)
C1	0.061 (3)	0.060 (3)	0.116 (4)	−0.007 (2)	0.016 (3)	−0.014 (3)
C4	0.115 (5)	0.080 (4)	0.089 (4)	−0.023 (4)	0.038 (3)	−0.020 (3)
C2	0.070 (4)	0.081 (4)	0.163 (7)	−0.003 (3)	0.048 (4)	−0.023 (4)
C3	0.126 (6)	0.093 (5)	0.141 (7)	−0.029 (5)	0.076 (5)	−0.039 (5)

Geometric parameters (Å, º)

Cu1—O2^i	1.957 (3)	C8—H8	0.9300
Cu1—O2	1.957 (3)	C14—C13	1.532 (6)
Cu1—O1	2.789 (3)	C13—H13A	0.9700
Cu1—N2^i	1.973 (4)	C13—H13B	0.9700
Cu1—N2	1.973 (4)	C6—C5	1.385 (7)
Cl2—C5	1.747 (6)	C6—C1	1.390 (7)
Cl1—C1	1.749 (6)	C17—H17	0.9300
O2—C14	1.297 (6)	C16—C15	1.349 (7)
O1—C14	1.219 (5)	C16—H16	0.9300
N2—C17	1.319 (6)	C9—C10	1.363 (8)
N2—C15	1.373 (6)	C9—H9	0.9300
N1—C6	1.386 (6)	C15—H15	0.9300
N1—C7	1.411 (6)	C11—C10	1.388 (8)
N1—H1	0.8600	C11—H11	0.9300
N3—C17	1.325 (6)	C5—C4	1.375 (7)
N3—C16	1.353 (7)	C10—H10	0.9300
N3—H3	0.8600	C1—C2	1.392 (8)
C7—C8	1.379 (6)	C4—C3	1.358 (10)
C7—C12	1.406 (6)	C4—H4	0.9300
C12—C11	1.386 (7)	C2—C3	1.393 (10)
C12—C13	1.502 (6)	C2—H2	0.9300
C8—C9	1.365 (7)	C3—H3A	0.9300
O2^i—Cu1—O2	180.0	C5—C6—N1	122.6 (4)
O2^i—Cu1—N2^i	88.81 (14)	C5—C6—C1	115.2 (5)
O2—Cu1—N2^i	91.19 (14)	N1—C6—C1	121.9 (5)
O2—Cu1—N2	88.81 (14)	N2—C17—N3	111.1 (4)
N2^i—Cu1—N2	180.0 (2)	N2—C17—H17	124.4
O1—Cu1—O2	52.32 (12)	N3—C17—H17	124.4
O1^i—Cu1—O2	127.68 (12)	C15—C16—N3	106.3 (5)
N2^i—Cu1—O1	85.76 (2)	C15—C16—H16	126.9
C14—O2—Cu1	110.5 (3)	N3—C16—H16	126.9
C17—N2—C15	105.3 (4)	C10—C9—C8	120.2 (5)
C17—N2—Cu1	126.5 (3)	C10—C9—H9	119.9
C15—N2—Cu1	127.6 (3)	C8—C9—H9	119.9
C6—N1—C7	121.7 (4)	C16—C15—N2	109.3 (5)
C6—N1—H1	119.1	C16—C15—H15	125.4
C7—N1—H1	119.1	N2—C15—H15	125.4
C17—N3—C16	108.0 (4)	C12—C11—C10	122.1 (5)
C17—N3—H3	126.0	C12—C11—H11	119.0
C16—N3—H3	126.0	C10—C11—H11	119.0
C8—C7—C12	119.2 (4)	C4—C5—C6	123.9 (6)
C8—C7—N1	122.4 (4)	C4—C5—Cl2	117.7 (5)
C12—C7—N1	118.5 (4)	C6—C5—Cl2	118.4 (4)
C11—C12—C7	117.7 (4)	C9—C10—C11	119.0 (5)
C11—C12—C13	120.1 (4)	C9—C10—H10	120.5
C7—C12—C13	122.2 (4)	C11—C10—H10	120.5
C9—C8—C7	121.8 (5)	C6—C1—C2	122.8 (6)
C9—C8—H8	119.1	C6—C1—Cl1	118.9 (4)
C7—C8—H8	119.1	C2—C1—Cl1	118.3 (5)
O1—C14—O2	124.0 (4)	C3—C4—C5	118.9 (7)
O1—C14—C13	121.7 (5)	C3—C4—H4	120.5
O2—C14—C13	114.3 (4)	C5—C4—H4	120.5
C12—C13—C14	109.3 (4)	C1—C2—C3	118.3 (6)
C12—C13—H13A	109.8	C1—C2—H2	120.9
C14—C13—H13A	109.8	C3—C2—H2	120.9
C12—C13—H13B	109.8	C4—C3—C2	120.8 (6)
C14—C13—H13B	109.8	C4—C3—H3A	119.6
H13A—C13—H13B	108.3	C2—C3—H3A	119.6
C6—N1—C7—C8	13.2 (7)	N3—C16—C15—N2	0.5 (6)
C6—N1—C7—C12	−168.1 (4)	C17—N2—C15—C16	−0.4 (5)
C8—C7—C12—C11	2.4 (6)	Cu1—N2—C15—C16	171.4 (3)
N1—C7—C12—C11	−176.3 (4)	C7—C12—C11—C10	−1.6 (7)
C8—C7—C12—C13	−179.3 (4)	C13—C12—C11—C10	−179.9 (5)
N1—C7—C12—C13	2.0 (6)	N1—C6—C5—C4	178.7 (5)
C12—C7—C8—C9	−1.9 (7)	C1—C6—C5—C4	4.3 (8)
N1—C7—C8—C9	176.8 (5)	N1—C6—C5—Cl2	0.8 (7)
Cu1—O2—C14—O1	3.1 (6)	C1—C6—C5—Cl2	−173.6 (4)
Cu1—O2—C14—C13	−174.0 (3)	C8—C9—C10—C11	0.6 (9)
C11—C12—C13—C14	95.2 (5)	C12—C11—C10—C9	0.1 (9)
C7—C12—C13—C14	−83.1 (6)	C5—C6—C1—C2	−1.3 (8)
O1—C14—C13—C12	−100.3 (5)	N1—C6—C1—C2	−175.8 (5)
O2—C14—C13—C12	76.9 (5)	C5—C6—C1—Cl1	178.9 (4)
C7—N1—C6—C5	66.0 (6)	N1—C6—C1—Cl1	4.5 (7)
C7—N1—C6—C1	−119.9 (5)	C6—C5—C4—C3	−4.0 (9)
C15—N2—C17—N3	0.1 (5)	Cl2—C5—C4—C3	173.9 (5)
Cu1—N2—C17—N3	−171.8 (3)	C6—C1—C2—C3	−1.7 (10)
C16—N3—C17—N2	0.2 (5)	Cl1—C1—C2—C3	178.0 (5)
C17—N3—C16—C15	−0.4 (5)	C5—C4—C3—C2	0.6 (10)
C7—C8—C9—C10	0.3 (8)	C1—C2—C3—C4	2.2 (11)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.27	2.900 (5)	130
N3—H3···O1^ii	0.86	1.96	2.791 (5)	163
C16—H16···Cl1^iii	0.93	2.92	3.791 (6)	156

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

Table S1. Selected IR spectral data for the dicl ligands 1, 2 and 3

Assignment	Nadicl	1	2	3
ν(NH)	3250 (m)	3326 (w)	3232 (w)	3259 (w), 3140 (w)
ν(O—H)		3554 (w)
νar(C—H)	3060 (vw)	3066 (vw)	3140 (w), 3112 (vw)	3075 (w)
νas(COO)	1572 (s)	1577 (s)	1561 (s)	1560 (s)
νs(COO)	1402 (w)	1416 (m)	1453 (m)	1451 (m)
Δν	171	161	108	109

Note: (*) Frequencies in cm^-1; w = weak; m = medium; s = strong; vs = very strong. Nadicl is sodium 2-[2-(2,6-dichloroanilino)phenyl]acetate.

Table S2. Comparative structural parameters for binuclear copper (II) carboxylates containing the [Cu2(syn,syn-µ₂-O₂CR)₄] core.

Complex	Cu···Cu (Å)	ΔCu (Å)	Cu—O(axial) (Å)	Cu—O(basal) (Å)**	Bridge length (Å)***
[Cu2(OCOCH3)4(DMF)2]	2.614 (1)	0.20	2.163 (3)	1.964 (3)	6.42
[Cu2(OCOCH3)4(MeOH)2]	2.596 (1)	0.18	2.160 (3)	1.967 (2)	6.46
[Cu2(dicl)4(DMF)2]	2.627 (1)	0.203	2.122 (2)	1.967 (2)	6.42
[Cu2(dicl)4(acetone)2]	2.610 (1)	0.191	2.177 (2)	1.970 (2)	6.45
[Cu2(dicl)4(MeOH)2]	2.585 (1)	0.176	2.187 (1)	1.961 (2)	6.45

Note: (*) deviation of copper from the basal plane; (**) average distance; (***) sum of Cu—O–C—O—Cu.