A dinuclear copper complex: bis-(μ-4-amino-benzoato)bis-[aqua(1,10-phenanthroline)copper(II)] dichloride bis(4-amino-benzoic acid) dihydrate.

The title complex, [Cu(2)(C(7)H(6)NO(2))(2)(C(12)H(8)N(2))(2)(H(2)O)(2)]·2C(7)H(7)NO(2)·2H(2)O, consists of a dinuclear [Cu(2)(C(7)H(6)NO(2))(2)(C(12)H(8)N(2))(2)(H(2)O)(2)](2+) cation, two Cl(-) anions, two 4-amino-benzoic acid mol-ecules and two disordered water mol-ecules (site occupancy factors 0.5). The Cu(II) ion adopts a distorted square-pyramidal geometry formed by two N atoms from the 1,10-phenanthroline ligand and two O atoms of the two 4-amino-benzoic acid ligands and one water O atom. The Cu⋯Cu separation is 3.109 (2) Å. A twofold axis passes through the mid-point of the Cu⋯Cu vector.

Related literature

For related literature, see: Lo et al. (2000 ▶); Zoroddu et al. (1996 ▶); Rao et al. (2004 ▶); Müller et al. (2003 ▶).

Experimental

Crystal data

[Cu2(C7H6NO2)2(C12H8N2)2(H2O)2]·2C7H7NO2·2H2O

M = 1174.96

Monoclinic,

a = 25.748 (2) Å

b = 10.0988 (8) Å

c = 20.9156 (17) Å

β = 110.3070 (10)°

V = 5100.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.01 mm−1

T = 291 (2) K

0.49 × 0.40 × 0.37 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.638, T max = 0.708

18514 measured reflections

4744 independent reflections

3886 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.02

4744 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023647/pv2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023647/pv2085Isup2.hkl

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

[Cu2(C7H6NO2)2(C12H8N2)2(H2O)2]·2C7H7NO2·2H2O	F000 = 2416
Mr = 1174.96	Dx = 1.530 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5516 reflections
a = 25.748 (2) Å	θ = 2.3–24.7º
b = 10.0988 (8) Å	µ = 1.01 mm−1
c = 20.9156 (17) Å	T = 291 (2) K
β = 110.3070 (10)º	Block, blue
V = 5100.5 (7) Å3	0.49 × 0.40 × 0.37 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4744 independent reflections
Radiation source: fine-focus sealed tube	3886 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 291(2) K	θmax = 25.5º
φ & ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −31→31
Tmin = 0.638, Tmax = 0.708	k = −12→12
18514 measured reflections	l = −24→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0477P)2 + 4.1583P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4744 reflections	Δρmax = 0.49 e Å−3
352 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. Yield 81%. IR(KBr): 3409(s), 3190(w), 3057(w), 2921(m), 2857(w), 1734(w), 1671(s), 1630(s), 1600(versus), 1550(s), 1516(s), 1494(w), 1418(m), 1389(versus), 1344(w), 1312(m), 1267(s), 1222(vw), 1178(s), 1146(m), 1108(m), 1046(w), 854(s), 844(s), 786(m), 719(s), 702(w), 643(m), 609(m), 511(m), 466(w), 430(w).

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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)
Cu1	0.018177 (11)	−0.03851 (3)	0.186473 (14)	0.03323 (10)
Cl1	0.18713 (3)	−0.11806 (7)	0.16975 (4)	0.0568 (2)
O1	0.2421 (2)	0.7015 (7)	0.0622 (3)	0.117 (2)	0.50
H2W	0.2255	0.7481	0.0828	0.176*	0.50
H1W	0.2651	0.7497	0.0492	0.176*	0.50
O2	0.29142 (16)	0.4893 (4)	0.10037 (19)	0.0606 (10)	0.50
H4W	0.2905	0.5658	0.0865	0.091*	0.50
H3W	0.2722	0.4821	0.1246	0.091*	0.50
O4	0.06914 (7)	−0.15420 (17)	0.25246 (9)	0.0441 (4)
O3	0.05793 (6)	−0.10211 (15)	0.10938 (8)	0.0389 (4)
H5W	0.0910	−0.1233	0.1281	0.058*
H6W	0.0554	−0.0384	0.0830	0.058*
O5	0.04104 (7)	−0.16729 (16)	0.34272 (8)	0.0416 (4)
O6	0.05048 (8)	0.10828 (17)	0.02418 (10)	0.0561 (5)
O7	0.00758 (7)	0.29085 (17)	−0.02501 (9)	0.0500 (4)
N1	−0.03250 (8)	0.10025 (19)	0.12729 (10)	0.0363 (4)
N2	0.06502 (8)	0.12213 (19)	0.22432 (10)	0.0367 (4)
N3	0.26796 (11)	−0.4815 (3)	0.45449 (15)	0.0914 (11)
H3A	0.2899	−0.5052	0.4336	0.110*
H3B	0.2751	−0.5037	0.4964	0.110*
N4	0.22137 (10)	0.5522 (2)	0.18975 (12)	0.0609 (7)
H4A	0.2511	0.5160	0.2169	0.073*
H4B	0.2188	0.6370	0.1867	0.073*
C1	0.07507 (9)	−0.1908 (2)	0.31242 (12)	0.0338 (5)
C2	0.12577 (9)	−0.2661 (2)	0.35019 (11)	0.0323 (5)
C3	0.13794 (10)	−0.2994 (3)	0.41806 (12)	0.0441 (6)
H3D	0.1137	−0.2744	0.4400	0.053*
C4	0.18489 (11)	−0.3682 (3)	0.45348 (13)	0.0539 (7)
H4	0.1925	−0.3883	0.4992	0.065*
C5	0.22162 (11)	−0.4085 (3)	0.42110 (14)	0.0515 (7)
C6	0.21002 (10)	−0.3726 (2)	0.35347 (13)	0.0411 (6)
H6	0.2343	−0.3967	0.3314	0.049*
C7	0.16336 (10)	−0.3024 (2)	0.31893 (12)	0.0363 (5)
H7A	0.1566	−0.2785	0.2738	0.044*
C8	−0.08038 (11)	0.0855 (3)	0.07639 (13)	0.0480 (6)
H8	−0.0935	0.0003	0.0632	0.058*
C9	−0.11160 (12)	0.1930 (3)	0.04215 (14)	0.0582 (8)
H9	−0.1447	0.1792	0.0062	0.070*
C10	−0.09364 (12)	0.3183 (3)	0.06132 (14)	0.0556 (7)
H10	−0.1150	0.3903	0.0396	0.067*
C11	−0.04277 (11)	0.3387 (2)	0.11407 (13)	0.0438 (6)
C12	−0.01910 (14)	0.4660 (3)	0.13788 (16)	0.0540 (7)
H12	−0.0383	0.5422	0.1183	0.065*
C13	0.03050 (14)	0.4771 (3)	0.18812 (16)	0.0553 (8)
H13	0.0448	0.5608	0.2025	0.066*
C14	0.06162 (11)	0.3625 (2)	0.21979 (13)	0.0438 (6)
C15	0.11401 (13)	0.3645 (3)	0.27098 (15)	0.0593 (8)
H15	0.1308	0.4450	0.2876	0.071*
C16	0.14047 (12)	0.2497 (3)	0.29647 (15)	0.0612 (8)
H16	0.1754	0.2516	0.3300	0.073*
C17	0.11497 (11)	0.1290 (3)	0.27211 (14)	0.0497 (7)
H17	0.1335	0.0508	0.2898	0.060*
C18	0.03912 (10)	0.2371 (2)	0.19804 (12)	0.0358 (5)
C19	−0.01349 (10)	0.2252 (2)	0.14510 (11)	0.0349 (5)
C20	0.04919 (10)	0.2283 (2)	0.02199 (12)	0.0386 (6)
C21	0.09205 (10)	0.3146 (2)	0.06716 (12)	0.0364 (5)
C22	0.08804 (10)	0.4523 (2)	0.06392 (12)	0.0393 (5)
H22	0.0565	0.4916	0.0335	0.047*
C23	0.13002 (11)	0.5308 (2)	0.10500 (13)	0.0440 (6)
H23	0.1265	0.6224	0.1020	0.053*
C24	0.17799 (10)	0.4743 (3)	0.15117 (12)	0.0422 (6)
C25	0.18133 (11)	0.3366 (3)	0.15532 (13)	0.0486 (6)
H25	0.2125	0.2971	0.1865	0.058*
C26	0.13959 (11)	0.2583 (3)	0.11425 (12)	0.0436 (6)
H26	0.1429	0.1666	0.1177	0.052*

	U11	U22	U33	U12	U13	U23
Cu1	0.02996 (16)	0.03028 (16)	0.03771 (17)	−0.00293 (11)	0.00953 (12)	0.00503 (12)
Cl1	0.0428 (4)	0.0556 (4)	0.0662 (5)	−0.0092 (3)	0.0117 (3)	0.0103 (3)
O1	0.077 (4)	0.185 (6)	0.079 (4)	−0.016 (4)	0.014 (3)	0.018 (4)
O2	0.063 (3)	0.070 (3)	0.045 (2)	−0.003 (2)	0.0136 (19)	−0.0081 (19)
O4	0.0407 (9)	0.0462 (10)	0.0469 (10)	0.0072 (8)	0.0169 (8)	0.0165 (8)
O3	0.0351 (9)	0.0391 (9)	0.0410 (9)	0.0007 (7)	0.0113 (7)	0.0082 (7)
O5	0.0380 (9)	0.0419 (9)	0.0465 (10)	0.0118 (7)	0.0166 (8)	0.0016 (8)
O6	0.0755 (14)	0.0345 (10)	0.0529 (11)	−0.0070 (9)	0.0154 (10)	0.0066 (8)
O7	0.0495 (10)	0.0397 (10)	0.0520 (11)	0.0027 (8)	0.0062 (9)	0.0031 (8)
N1	0.0353 (10)	0.0365 (11)	0.0361 (11)	−0.0009 (9)	0.0111 (9)	0.0023 (9)
N2	0.0331 (10)	0.0374 (11)	0.0373 (11)	−0.0048 (9)	0.0095 (9)	0.0034 (9)
N3	0.0673 (18)	0.142 (3)	0.0690 (18)	0.0646 (19)	0.0284 (15)	0.0421 (19)
N4	0.0495 (14)	0.0600 (16)	0.0599 (15)	−0.0008 (12)	0.0019 (12)	−0.0113 (12)
C1	0.0342 (12)	0.0238 (11)	0.0429 (13)	−0.0006 (9)	0.0128 (11)	0.0010 (10)
C2	0.0327 (12)	0.0260 (11)	0.0388 (12)	0.0016 (9)	0.0134 (10)	0.0024 (9)
C3	0.0414 (14)	0.0528 (16)	0.0435 (14)	0.0109 (12)	0.0217 (12)	0.0064 (12)
C4	0.0495 (16)	0.076 (2)	0.0372 (14)	0.0200 (14)	0.0157 (12)	0.0175 (13)
C5	0.0407 (14)	0.0609 (17)	0.0525 (16)	0.0171 (13)	0.0158 (12)	0.0143 (14)
C6	0.0351 (13)	0.0425 (14)	0.0504 (15)	0.0054 (11)	0.0209 (11)	0.0032 (11)
C7	0.0394 (13)	0.0324 (12)	0.0401 (13)	0.0003 (10)	0.0178 (11)	0.0041 (10)
C8	0.0414 (14)	0.0509 (16)	0.0456 (15)	−0.0030 (12)	0.0074 (12)	0.0005 (12)
C9	0.0472 (16)	0.068 (2)	0.0487 (16)	0.0102 (15)	0.0031 (13)	0.0110 (15)
C10	0.0576 (17)	0.0569 (18)	0.0518 (16)	0.0170 (14)	0.0181 (14)	0.0209 (14)
C11	0.0547 (16)	0.0399 (14)	0.0438 (14)	0.0092 (12)	0.0261 (13)	0.0113 (11)
C12	0.074 (2)	0.0357 (14)	0.0630 (18)	0.0076 (14)	0.0373 (17)	0.0108 (13)
C13	0.082 (2)	0.0323 (14)	0.068 (2)	−0.0069 (14)	0.0465 (19)	−0.0047 (13)
C14	0.0550 (16)	0.0373 (13)	0.0464 (14)	−0.0112 (12)	0.0267 (13)	−0.0077 (11)
C15	0.068 (2)	0.0518 (17)	0.0625 (18)	−0.0276 (16)	0.0289 (16)	−0.0162 (15)
C16	0.0493 (17)	0.070 (2)	0.0561 (18)	−0.0207 (15)	0.0077 (14)	−0.0072 (16)
C17	0.0398 (14)	0.0534 (16)	0.0495 (15)	−0.0067 (12)	0.0072 (12)	0.0056 (13)
C18	0.0419 (13)	0.0352 (12)	0.0362 (12)	−0.0046 (10)	0.0210 (11)	0.0007 (10)
C19	0.0412 (13)	0.0344 (12)	0.0332 (12)	−0.0002 (10)	0.0181 (10)	0.0034 (10)
C20	0.0483 (15)	0.0356 (14)	0.0384 (13)	−0.0007 (11)	0.0234 (12)	0.0034 (10)
C21	0.0414 (13)	0.0370 (13)	0.0343 (12)	0.0019 (11)	0.0176 (10)	0.0034 (10)
C22	0.0395 (13)	0.0389 (13)	0.0376 (13)	0.0043 (11)	0.0111 (11)	0.0055 (11)
C23	0.0498 (15)	0.0359 (14)	0.0452 (14)	0.0039 (12)	0.0153 (12)	0.0022 (11)
C24	0.0419 (14)	0.0496 (16)	0.0362 (13)	−0.0001 (12)	0.0148 (11)	−0.0044 (11)
C25	0.0442 (15)	0.0526 (16)	0.0441 (15)	0.0140 (13)	0.0089 (12)	0.0028 (12)
C26	0.0507 (15)	0.0367 (13)	0.0443 (14)	0.0103 (12)	0.0176 (12)	0.0045 (11)

Cu1—O4	1.9326 (16)	C6—C7	1.366 (3)
Cu1—O5i	1.9346 (16)	C6—H6	0.9300
Cu1—N2	2.0125 (19)	C7—H7A	0.9300
Cu1—N1	2.0192 (19)	C8—C9	1.393 (4)
Cu1—O3	2.2815 (16)	C8—H8	0.9300
O1—H2W	0.8467	C9—C10	1.358 (4)
O1—H1W	0.8810	C9—H9	0.9300
O2—H4W	0.8235	C10—C11	1.404 (4)
O2—H3W	0.8250	C10—H10	0.9300
O4—C1	1.265 (3)	C11—C19	1.401 (3)
O3—H5W	0.8317	C11—C12	1.436 (4)
O3—H6W	0.8354	C12—C13	1.348 (4)
O5—C1	1.269 (3)	C12—H12	0.9300
O5—Cu1i	1.9346 (16)	C13—C14	1.432 (4)
O6—C20	1.213 (3)	C13—H13	0.9300
O7—C20	1.335 (3)	C14—C18	1.401 (3)
N1—C8	1.328 (3)	C14—C15	1.401 (4)
N1—C19	1.358 (3)	C15—C16	1.356 (4)
N2—C17	1.329 (3)	C15—H15	0.9300
N2—C18	1.357 (3)	C16—C17	1.395 (4)
N3—C5	1.370 (3)	C16—H16	0.9300
N3—H3A	0.8600	C17—H17	0.9300
N3—H3B	0.8600	C18—C19	1.426 (3)
N4—C24	1.375 (3)	C20—C21	1.465 (3)
N4—H4A	0.8600	C21—C22	1.394 (3)
N4—H4B	0.8600	C21—C26	1.398 (3)
C1—C2	1.480 (3)	C22—C23	1.375 (3)
C2—C3	1.385 (3)	C22—H22	0.9300
C2—C7	1.392 (3)	C23—C24	1.399 (3)
C3—C4	1.368 (3)	C23—H23	0.9300
C3—H3D	0.9300	C24—C25	1.394 (4)
C4—C5	1.401 (4)	C25—C26	1.370 (4)
C4—H4	0.9300	C25—H25	0.9300
C5—C6	1.389 (4)	C26—H26	0.9300
O4—Cu1—O5i	94.84 (7)	C10—C9—H9	120.1
O4—Cu1—N2	92.34 (8)	C8—C9—H9	120.1
O5i—Cu1—N2	164.82 (8)	C9—C10—C11	119.8 (3)
O4—Cu1—N1	172.52 (8)	C9—C10—H10	120.1
O5i—Cu1—N1	90.13 (7)	C11—C10—H10	120.1
N2—Cu1—N1	81.56 (8)	C19—C11—C10	116.7 (2)
O4—Cu1—O3	88.54 (6)	C19—C11—C12	118.4 (2)
O5i—Cu1—O3	94.90 (6)	C10—C11—C12	124.9 (3)
N2—Cu1—O3	98.65 (7)	C13—C12—C11	121.2 (3)
N1—Cu1—O3	96.61 (7)	C13—C12—H12	119.4
H2W—O1—H1W	111.3	C11—C12—H12	119.4
H4W—O2—H3W	110.4	C12—C13—C14	121.3 (3)
C1—O4—Cu1	134.68 (15)	C12—C13—H13	119.3
Cu1—O3—H5W	112.1	C14—C13—H13	119.3
Cu1—O3—H6W	107.4	C18—C14—C15	116.2 (3)
H5W—O3—H6W	110.0	C18—C14—C13	118.5 (2)
C1—O5—Cu1i	124.96 (15)	C15—C14—C13	125.3 (3)
C8—N1—C19	118.0 (2)	C16—C15—C14	120.5 (3)
C8—N1—Cu1	129.48 (18)	C16—C15—H15	119.8
C19—N1—Cu1	112.46 (15)	C14—C15—H15	119.8
C17—N2—C18	118.1 (2)	C15—C16—C17	119.7 (3)
C17—N2—Cu1	128.99 (18)	C15—C16—H16	120.2
C18—N2—Cu1	112.80 (15)	C17—C16—H16	120.2
C5—N3—H3A	120.0	N2—C17—C16	122.0 (3)
C5—N3—H3B	120.0	N2—C17—H17	119.0
H3A—N3—H3B	120.0	C16—C17—H17	119.0
C24—N4—H4A	120.0	N2—C18—C14	123.5 (2)
C24—N4—H4B	120.0	N2—C18—C19	116.3 (2)
H4A—N4—H4B	120.0	C14—C18—C19	120.2 (2)
O4—C1—O5	125.0 (2)	N1—C19—C11	123.2 (2)
O4—C1—C2	117.4 (2)	N1—C19—C18	116.5 (2)
O5—C1—C2	117.6 (2)	C11—C19—C18	120.3 (2)
C3—C2—C7	118.1 (2)	O6—C20—O7	120.3 (2)
C3—C2—C1	121.0 (2)	O6—C20—C21	124.4 (2)
C7—C2—C1	120.9 (2)	O7—C20—C21	115.2 (2)
C4—C3—C2	121.4 (2)	C22—C21—C26	118.2 (2)
C4—C3—H3D	119.3	C22—C21—C20	122.4 (2)
C2—C3—H3D	119.3	C26—C21—C20	119.4 (2)
C3—C4—C5	120.2 (2)	C23—C22—C21	121.1 (2)
C3—C4—H4	119.9	C23—C22—H22	119.5
C5—C4—H4	119.9	C21—C22—H22	119.5
N3—C5—C6	120.1 (2)	C22—C23—C24	120.7 (2)
N3—C5—C4	121.6 (3)	C22—C23—H23	119.6
C6—C5—C4	118.3 (2)	C24—C23—H23	119.6
C7—C6—C5	120.9 (2)	N4—C24—C25	120.9 (2)
C7—C6—H6	119.6	N4—C24—C23	121.0 (2)
C5—C6—H6	119.6	C25—C24—C23	118.1 (2)
C6—C7—C2	121.0 (2)	C26—C25—C24	121.2 (2)
C6—C7—H7A	119.5	C26—C25—H25	119.4
C2—C7—H7A	119.5	C24—C25—H25	119.4
N1—C8—C9	122.3 (3)	C25—C26—C21	120.7 (2)
N1—C8—H8	118.9	C25—C26—H26	119.6
C9—C8—H8	118.9	C21—C26—H26	119.6
C10—C9—C8	119.9 (3)
O5i—Cu1—O4—C1	−79.3 (2)	C11—C12—C13—C14	0.0 (4)
N2—Cu1—O4—C1	87.3 (2)	C12—C13—C14—C18	−0.8 (4)
O3—Cu1—O4—C1	−174.1 (2)	C12—C13—C14—C15	178.2 (3)
O5i—Cu1—N1—C8	−16.4 (2)	C18—C14—C15—C16	0.5 (4)
N2—Cu1—N1—C8	176.4 (2)	C13—C14—C15—C16	−178.5 (3)
O3—Cu1—N1—C8	78.6 (2)	C14—C15—C16—C17	−0.8 (5)
O5i—Cu1—N1—C19	162.21 (16)	C18—N2—C17—C16	1.4 (4)
N2—Cu1—N1—C19	−5.03 (15)	Cu1—N2—C17—C16	−175.2 (2)
O3—Cu1—N1—C19	−102.84 (15)	C15—C16—C17—N2	−0.2 (5)
O4—Cu1—N2—C17	6.6 (2)	C17—N2—C18—C14	−1.7 (3)
O5i—Cu1—N2—C17	124.8 (3)	Cu1—N2—C18—C14	175.41 (18)
N1—Cu1—N2—C17	−177.8 (2)	C17—N2—C18—C19	177.7 (2)
O3—Cu1—N2—C17	−82.3 (2)	Cu1—N2—C18—C19	−5.2 (2)
O4—Cu1—N2—C18	−170.09 (16)	C15—C14—C18—N2	0.7 (4)
O5i—Cu1—N2—C18	−51.9 (4)	C13—C14—C18—N2	179.8 (2)
N1—Cu1—N2—C18	5.57 (15)	C15—C14—C18—C19	−178.6 (2)
O3—Cu1—N2—C18	101.03 (15)	C13—C14—C18—C19	0.5 (3)
Cu1—O4—C1—O5	9.1 (4)	C8—N1—C19—C11	2.3 (3)
Cu1—O4—C1—C2	−170.59 (15)	Cu1—N1—C19—C11	−176.46 (18)
Cu1i—O5—C1—O4	−14.8 (3)	C8—N1—C19—C18	−177.5 (2)
Cu1i—O5—C1—C2	164.80 (15)	Cu1—N1—C19—C18	3.7 (2)
O4—C1—C2—C3	174.1 (2)	C10—C11—C19—N1	−1.2 (4)
O5—C1—C2—C3	−5.6 (3)	C12—C11—C19—N1	178.9 (2)
O4—C1—C2—C7	−4.2 (3)	C10—C11—C19—C18	178.6 (2)
O5—C1—C2—C7	176.1 (2)	C12—C11—C19—C18	−1.3 (3)
C7—C2—C3—C4	−1.3 (4)	N2—C18—C19—N1	1.0 (3)
C1—C2—C3—C4	−179.6 (2)	C14—C18—C19—N1	−179.6 (2)
C2—C3—C4—C5	−1.0 (4)	N2—C18—C19—C11	−178.8 (2)
C3—C4—C5—N3	−177.7 (3)	C14—C18—C19—C11	0.6 (3)
C3—C4—C5—C6	2.3 (4)	O6—C20—C21—C22	−178.2 (2)
N3—C5—C6—C7	178.5 (3)	O7—C20—C21—C22	3.6 (3)
C4—C5—C6—C7	−1.5 (4)	O6—C20—C21—C26	3.5 (4)
C5—C6—C7—C2	−0.7 (4)	O7—C20—C21—C26	−174.7 (2)
C3—C2—C7—C6	2.1 (4)	C26—C21—C22—C23	1.1 (4)
C1—C2—C7—C6	−179.6 (2)	C20—C21—C22—C23	−177.2 (2)
C19—N1—C8—C9	−1.2 (4)	C21—C22—C23—C24	0.1 (4)
Cu1—N1—C8—C9	177.4 (2)	C22—C23—C24—N4	176.5 (2)
N1—C8—C9—C10	−1.0 (4)	C22—C23—C24—C25	−1.4 (4)
C8—C9—C10—C11	2.1 (4)	N4—C24—C25—C26	−176.2 (2)
C9—C10—C11—C19	−1.1 (4)	C23—C24—C25—C26	1.7 (4)
C9—C10—C11—C12	178.8 (3)	C24—C25—C26—C21	−0.5 (4)
C19—C11—C12—C13	1.0 (4)	C22—C21—C26—C25	−0.9 (4)
C10—C11—C12—C13	−178.8 (3)	C20—C21—C26—C25	177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2W···Cl1ii	0.85	2.71	3.549 (7)	170
O1—H1W···O1iii	0.88	2.32	2.938 (11)	127
O2—H4W···O1	0.82	1.80	2.477 (8)	138
O2—H3W···N4	0.83	2.30	3.081 (5)	157
O3—H5W···Cl1	0.83	2.32	3.1259 (17)	163
O3—H6W···O6	0.84	1.90	2.737 (2)	179
N3—H3A···Cl1iv	0.86	2.68	3.475 (3)	154
N3—H3B···O2v	0.86	2.07	2.898 (5)	161
N4—H4A···Cl1vi	0.86	2.71	3.512 (3)	155
N4—H4B···Cl1ii	0.86	2.59	3.433 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H2W⋯Cl1i	0.85	2.71	3.549 (7)	170
O1—H1W⋯O1ii	0.88	2.32	2.938 (11)	127
O2—H4W⋯O1	0.82	1.80	2.477 (8)	138
O2—H3W⋯N4	0.83	2.30	3.081 (5)	157
O3—H5W⋯Cl1	0.83	2.32	3.1259 (17)	163
O3—H6W⋯O6	0.84	1.90	2.737 (2)	179
N3—H3A⋯Cl1iii	0.86	2.68	3.475 (3)	154
N3—H3B⋯O2iv	0.86	2.07	2.898 (5)	161
N4—H4A⋯Cl1v	0.86	2.71	3.512 (3)	155
N4—H4B⋯Cl1i	0.86	2.59	3.433 (3)	167

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