catena-Poly[[[bis-(4-amino-benzoato-κO)copper(II)]-μ-1,1'-(pentane-1,5-di-yl)diimidazole] trihydrate].

In the title compound, {[Cu(C(7)H(6)NO(2))(2)(C(11)H(16)N(4))]·3H(2)O}(n), each Cu(II) atom is coordinated by two O atoms from two 4-amino-benzoate anions, and two N atoms from two different 1,1'-(pentane-1,5-di-yl)diimidazole (biim-5) ligands, to furnish a distorted square-planar geometry. The biim-5 ligand coordinates to two copper(II) cations, acting as a bridging ligand; as a result the copper(II) cations are connected to form an infinite chain structure. The polymeric chains are linked through a variety of hydrogen bonds to form a three-dimensional structure.

Related literature

For related literature, see: Batten & Robson (1998 ▶); Chen & Gao (2002 ▶); Ma et al. (2000 ▶); Moulton & Zaworotko (2001 ▶); Tong et al. (2002 ▶); Yang et al. (2005 ▶, 2006 ▶).

Experimental

Crystal data

[Cu(n class="CellLine">C7H6NO2)2(C11H16N4)]·3H2O

M = 594.12

Monoclinic,

a = 13.082 (9) Å

b = 11.151 (1) Å

c = 19.505 (2) Å

β = 93.725 (1)°

V = 2839.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.82 mm−1

T = 293 (2) K

0.68 × 0.45 × 0.38 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.635, T max = 0.746

16576 measured reflections

6488 independent reflections

4988 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.095

S = 1.03

6488 reflections

382 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 1990 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064586/sf2009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064586/sf2009Isup2.hkl

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

[Cu(C7H6NO2)2(C11H16N4)]·3H2O	F000 = 1244
Mr = 594.12	Dx = 1.390 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 6488 reflections
a = 13.082 (9) Å	θ = 1.8–28.5º
b = 11.151 (1) Å	µ = 0.82 mm−1
c = 19.505 (2) Å	T = 293 (2) K
β = 93.725 (1)º	Block, blue
V = 2839.3 (4) Å3	0.68 × 0.45 × 0.38 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	6488 independent reflections
Radiation source: fine-focus sealed tube	4988 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 293(2) K	θmax = 28.5º
ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −17→9
Tmin = 0.635, Tmax = 0.746	k = −14→13
16576 measured reflections	l = −25→26

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.6476P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.002
6488 reflections	Δρmax = 0.41 e Å−3
382 parameters	Δρmin = −0.34 e Å−3
12 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
Cu1	0.724906 (17)	0.20985 (2)	0.494309 (9)	0.03977 (9)
C1	0.69874 (15)	0.25416 (18)	0.70179 (8)	0.0414 (4)
C2	0.63431 (17)	0.1687 (2)	0.72737 (9)	0.0515 (5)
H2	0.5989	0.1165	0.6971	0.062*
C3	0.62168 (18)	0.1595 (2)	0.79711 (10)	0.0578 (5)
H3	0.5772	0.1024	0.8131	0.069*
C4	0.67506 (17)	0.2352 (2)	0.84349 (9)	0.0503 (5)
C5	0.74098 (18)	0.32010 (19)	0.81822 (10)	0.0521 (5)
H5	0.7778	0.3708	0.8485	0.063*
C6	0.75202 (17)	0.32954 (18)	0.74842 (10)	0.0480 (4)
H6	0.7958	0.3873	0.7323	0.058*
C7	0.71394 (15)	0.26575 (18)	0.62690 (9)	0.0437 (4)
C8	0.72368 (15)	0.13276 (17)	0.28845 (8)	0.0437 (4)
C9	0.66706 (18)	0.05414 (19)	0.24653 (10)	0.0543 (5)
H9	0.6230	0.0002	0.2659	0.065*
C10	0.6749 (2)	0.0543 (2)	0.17607 (10)	0.0605 (6)
H10	0.6364	0.0002	0.1488	0.073*
C11	0.73957 (18)	0.1343 (2)	0.14575 (9)	0.0531 (5)
C12	0.79721 (18)	0.21209 (19)	0.18774 (10)	0.0531 (5)
H12	0.8418	0.2653	0.1684	0.064*
C13	0.78948 (16)	0.21189 (18)	0.25818 (9)	0.0483 (5)
H13	0.8287	0.2652	0.2855	0.058*
C14	0.71565 (16)	0.1321 (2)	0.36461 (9)	0.0487 (5)
C15	0.88170 (14)	0.07802 (17)	0.58180 (9)	0.0418 (4)
H15	0.8333	0.0438	0.6087	0.050*
C16	0.95172 (16)	0.17479 (19)	0.50186 (10)	0.0484 (5)
H16	0.9602	0.2202	0.4626	0.058*
C17	1.02826 (16)	0.1299 (2)	0.54402 (10)	0.0536 (5)
H17	1.0982	0.1392	0.5396	0.064*
C18	1.03590 (17)	0.0044 (2)	0.65268 (10)	0.0568 (6)
H18A	1.0945	−0.0381	0.6367	0.068*
H18B	0.9898	−0.0544	0.6704	0.068*
C19	1.07186 (15)	0.0899 (2)	0.71027 (10)	0.0565 (5)
H19A	1.1139	0.0454	0.7443	0.068*
H19B	1.1148	0.1509	0.6914	0.068*
C20	0.98658 (16)	0.15138 (19)	0.74596 (10)	0.0529 (5)
H20A	1.0170	0.2083	0.7789	0.063*
H20B	0.9449	0.1964	0.7120	0.063*
C21	0.91748 (15)	0.0677 (2)	0.78300 (10)	0.0549 (5)
H21A	0.8871	0.0110	0.7499	0.066*
H21B	0.8622	0.1146	0.8003	0.066*
C22	0.96906 (17)	−0.00216 (19)	0.84230 (10)	0.0541 (5)
H22A	0.9211	−0.0603	0.8585	0.065*
H22B	1.0269	−0.0458	0.8261	0.065*
C23	1.09798 (15)	0.12327 (18)	0.90985 (9)	0.0438 (4)
H23	1.1518	0.1089	0.8820	0.053*
C24	1.00978 (16)	0.18889 (19)	0.99050 (10)	0.0501 (5)
H24	0.9912	0.2289	1.0296	0.060*
C25	0.94779 (16)	0.1173 (2)	0.95058 (10)	0.0546 (5)
H25	0.8794	0.0999	0.9566	0.065*
N1	0.85934 (12)	0.14264 (14)	0.52616 (7)	0.0413 (3)
N2	0.98308 (12)	0.06823 (15)	0.59449 (7)	0.0443 (4)
N3	1.00482 (12)	0.07559 (14)	0.89960 (7)	0.0429 (4)
N4	1.10431 (12)	0.19343 (14)	0.96448 (7)	0.0422 (4)
N5	0.6617 (2)	0.2274 (2)	0.91329 (9)	0.0714 (6)
N6	0.7484 (2)	0.1342 (2)	0.07524 (9)	0.0745 (7)
O1	0.67388 (10)	0.18549 (13)	0.58642 (6)	0.0461 (3)
O2	0.76375 (14)	0.35143 (14)	0.60610 (7)	0.0639 (4)
O1W	0.69005 (16)	−0.12845 (16)	0.48742 (9)	0.0730 (5)
O3	0.76716 (11)	0.21141 (14)	0.39921 (6)	0.0529 (4)
O2W	0.55952 (17)	−0.03625 (18)	0.58310 (12)	0.0875 (6)
O4	0.65989 (14)	0.05708 (15)	0.39138 (7)	0.0671 (4)
O3W	0.8944 (2)	0.4784 (2)	0.52971 (15)	0.1152 (9)
H5A	0.704 (3)	0.261 (4)	0.937 (2)	0.173*
H5B	0.638 (4)	0.161 (3)	0.927 (2)	0.173*
H6A	0.698 (3)	0.091 (4)	0.051 (2)	0.173*
H6B	0.774 (4)	0.199 (4)	0.058 (2)	0.173*
H1A	0.645 (3)	−0.104 (4)	0.5145 (18)	0.173*
H1B	0.691 (3)	−0.078 (4)	0.4530 (17)	0.173*
H2A	0.496 (2)	−0.038 (4)	0.593 (2)	0.173*
H2B	0.577 (3)	0.045 (3)	0.584 (2)	0.173*
H3A	0.845 (2)	0.436 (4)	0.547 (2)	0.173*
H3B	0.952 (2)	0.449 (4)	0.558 (2)	0.173*

	U11	U22	U33	U12	U13	U23
Cu1	0.04202 (14)	0.05555 (15)	0.02164 (11)	0.00707 (10)	0.00120 (8)	0.00176 (9)
C1	0.0499 (11)	0.0473 (10)	0.0272 (8)	0.0124 (9)	0.0031 (8)	0.0012 (7)
C2	0.0583 (12)	0.0659 (13)	0.0305 (9)	−0.0015 (10)	0.0036 (9)	−0.0037 (9)
C3	0.0654 (14)	0.0754 (14)	0.0333 (9)	−0.0059 (12)	0.0091 (9)	0.0021 (10)
C4	0.0611 (13)	0.0621 (13)	0.0282 (8)	0.0174 (10)	0.0062 (9)	−0.0008 (8)
C5	0.0675 (13)	0.0528 (12)	0.0353 (9)	0.0119 (10)	−0.0025 (9)	−0.0088 (8)
C6	0.0589 (12)	0.0454 (10)	0.0397 (9)	0.0064 (9)	0.0047 (9)	−0.0004 (8)
C7	0.0484 (11)	0.0519 (11)	0.0313 (9)	0.0139 (9)	0.0055 (8)	0.0052 (8)
C8	0.0519 (11)	0.0521 (11)	0.0274 (8)	0.0174 (9)	0.0044 (8)	0.0053 (8)
C9	0.0648 (13)	0.0584 (12)	0.0400 (10)	0.0036 (11)	0.0061 (10)	0.0058 (9)
C10	0.0808 (16)	0.0640 (14)	0.0361 (10)	0.0039 (12)	−0.0013 (10)	−0.0023 (10)
C11	0.0728 (14)	0.0586 (12)	0.0281 (8)	0.0209 (11)	0.0048 (9)	0.0041 (8)
C12	0.0677 (14)	0.0582 (12)	0.0346 (9)	0.0090 (10)	0.0111 (9)	0.0085 (9)
C13	0.0572 (12)	0.0550 (12)	0.0327 (9)	0.0100 (10)	0.0038 (8)	0.0013 (8)
C14	0.0523 (11)	0.0641 (13)	0.0302 (9)	0.0259 (10)	0.0063 (8)	0.0084 (9)
C15	0.0431 (10)	0.0515 (10)	0.0308 (8)	0.0052 (8)	0.0017 (7)	0.0023 (8)
C16	0.0497 (11)	0.0607 (12)	0.0354 (9)	0.0012 (10)	0.0068 (8)	0.0043 (9)
C17	0.0410 (10)	0.0758 (14)	0.0446 (10)	0.0005 (10)	0.0069 (9)	−0.0010 (10)
C18	0.0539 (12)	0.0754 (14)	0.0403 (10)	0.0257 (11)	−0.0038 (9)	0.0039 (10)
C19	0.0414 (10)	0.0871 (16)	0.0398 (10)	−0.0031 (11)	−0.0065 (8)	0.0059 (10)
C20	0.0565 (12)	0.0582 (12)	0.0419 (10)	0.0009 (10)	−0.0120 (9)	−0.0039 (9)
C21	0.0413 (10)	0.0783 (14)	0.0442 (10)	−0.0032 (10)	−0.0038 (9)	−0.0154 (10)
C22	0.0603 (13)	0.0522 (12)	0.0496 (11)	−0.0180 (10)	0.0012 (10)	−0.0102 (9)
C23	0.0428 (10)	0.0544 (11)	0.0343 (9)	−0.0051 (9)	0.0036 (8)	−0.0047 (8)
C24	0.0476 (11)	0.0656 (13)	0.0379 (10)	−0.0019 (10)	0.0077 (8)	−0.0067 (9)
C25	0.0414 (10)	0.0752 (14)	0.0479 (11)	−0.0067 (10)	0.0086 (9)	−0.0042 (10)
N1	0.0418 (8)	0.0544 (9)	0.0276 (7)	0.0055 (7)	0.0024 (6)	0.0011 (6)
N2	0.0422 (8)	0.0580 (10)	0.0321 (7)	0.0108 (7)	−0.0011 (6)	0.0000 (7)
N3	0.0445 (8)	0.0481 (9)	0.0358 (7)	−0.0073 (7)	0.0003 (7)	−0.0021 (7)
N4	0.0422 (8)	0.0558 (9)	0.0285 (7)	−0.0049 (7)	0.0018 (6)	−0.0013 (6)
N5	0.0936 (17)	0.0929 (17)	0.0282 (8)	0.0059 (13)	0.0091 (9)	−0.0018 (9)
N6	0.1137 (19)	0.0827 (15)	0.0279 (8)	0.0114 (13)	0.0109 (10)	0.0024 (9)
O1	0.0482 (7)	0.0655 (9)	0.0245 (6)	0.0049 (6)	0.0022 (5)	0.0000 (6)
O2	0.0887 (12)	0.0600 (9)	0.0449 (8)	−0.0038 (9)	0.0186 (8)	0.0064 (7)
O1W	0.0865 (12)	0.0683 (11)	0.0655 (11)	0.0060 (9)	0.0135 (9)	0.0146 (9)
O3	0.0486 (8)	0.0851 (11)	0.0250 (6)	0.0149 (7)	0.0024 (6)	0.0009 (6)
O2W	0.0846 (13)	0.0803 (13)	0.0985 (15)	−0.0034 (11)	0.0133 (12)	−0.0157 (11)
O4	0.0865 (12)	0.0744 (10)	0.0425 (8)	0.0088 (9)	0.0203 (8)	0.0176 (7)
O3W	0.130 (2)	0.0837 (15)	0.140 (2)	0.0016 (14)	0.0703 (18)	0.0213 (14)

Cu1—N4i	1.9677 (15)	C17—N2	1.367 (3)
Cu1—O3	1.9698 (12)	C17—H17	0.9300
Cu1—N1	1.9745 (15)	C18—N2	1.473 (2)
Cu1—O1	1.9757 (12)	C18—C19	1.524 (3)
C1—C2	1.387 (3)	C18—H18A	0.9700
C1—C6	1.392 (3)	C18—H18B	0.9700
C1—C7	1.493 (2)	C19—C20	1.517 (3)
C2—C3	1.385 (2)	C19—H19A	0.9700
C2—H2	0.9300	C19—H19B	0.9700
C3—C4	1.391 (3)	C20—C21	1.515 (3)
C3—H3	0.9300	C20—H20A	0.9700
C4—N5	1.387 (2)	C20—H20B	0.9700
C4—C5	1.392 (3)	C21—C22	1.516 (3)
C5—C6	1.382 (3)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C6—H6	0.9300	C22—N3	1.467 (2)
C7—O2	1.239 (2)	C22—H22A	0.9700
C7—O1	1.283 (2)	C22—H22B	0.9700
C8—C9	1.381 (3)	C23—N4	1.320 (2)
C8—C13	1.391 (3)	C23—N3	1.333 (2)
C8—C14	1.496 (2)	C23—H23	0.9300
C9—C10	1.385 (3)	C24—C25	1.349 (3)
C9—H9	0.9300	C24—N4	1.368 (2)
C10—C11	1.389 (3)	C24—H24	0.9300
C10—H10	0.9300	C25—N3	1.363 (2)
C11—C12	1.383 (3)	C25—H25	0.9300
C11—N6	1.387 (2)	N4—Cu1ii	1.9677 (15)
C12—C13	1.384 (3)	N5—H5A	0.79 (3)
C12—H12	0.9300	N5—H5B	0.86 (3)
C13—H13	0.9300	N6—H6A	0.92 (3)
C14—O4	1.247 (3)	N6—H6B	0.88 (4)
C14—O3	1.278 (3)	O1W—H1A	0.86 (3)
C15—N1	1.320 (2)	O1W—H1B	0.87 (3)
C15—N2	1.338 (2)	O2W—H2A	0.86 (3)
C15—H15	0.9300	O2W—H2B	0.94 (3)
C16—C17	1.350 (3)	O3W—H3A	0.89 (3)
C16—N1	1.374 (2)	O3W—H3B	0.97 (3)
C16—H16	0.9300
N4i—Cu1—O3	89.16 (6)	N2—C18—H18B	109.2
N4i—Cu1—N1	169.04 (7)	C19—C18—H18B	109.2
O3—Cu1—N1	90.06 (6)	H18A—C18—H18B	107.9
N4i—Cu1—O1	91.86 (6)	C20—C19—C18	114.84 (17)
O3—Cu1—O1	171.77 (6)	C20—C19—H19A	108.6
N1—Cu1—O1	90.48 (6)	C18—C19—H19A	108.6
C2—C1—C6	118.06 (16)	C20—C19—H19B	108.6
C2—C1—C7	122.31 (17)	C18—C19—H19B	108.6
C6—C1—C7	119.62 (18)	H19A—C19—H19B	107.5
C3—C2—C1	121.22 (19)	C21—C20—C19	114.83 (18)
C3—C2—H2	119.4	C21—C20—H20A	108.6
C1—C2—H2	119.4	C19—C20—H20A	108.6
C2—C3—C4	120.5 (2)	C21—C20—H20B	108.6
C2—C3—H3	119.8	C19—C20—H20B	108.6
C4—C3—H3	119.8	H20A—C20—H20B	107.5
N5—C4—C3	120.7 (2)	C20—C21—C22	115.50 (17)
N5—C4—C5	120.7 (2)	C20—C21—H21A	108.4
C3—C4—C5	118.60 (17)	C22—C21—H21A	108.4
C6—C5—C4	120.47 (19)	C20—C21—H21B	108.4
C6—C5—H5	119.8	C22—C21—H21B	108.4
C4—C5—H5	119.8	H21A—C21—H21B	107.5
C5—C6—C1	121.2 (2)	N3—C22—C21	112.43 (17)
C5—C6—H6	119.4	N3—C22—H22A	109.1
C1—C6—H6	119.4	C21—C22—H22A	109.1
O2—C7—O1	122.61 (16)	N3—C22—H22B	109.1
O2—C7—C1	119.56 (18)	C21—C22—H22B	109.1
O1—C7—C1	117.83 (17)	H22A—C22—H22B	107.8
C9—C8—C13	118.32 (17)	N4—C23—N3	111.48 (16)
C9—C8—C14	121.02 (19)	N4—C23—H23	124.3
C13—C8—C14	120.66 (19)	N3—C23—H23	124.3
C8—C9—C10	121.0 (2)	C25—C24—N4	109.38 (17)
C8—C9—H9	119.5	C25—C24—H24	125.3
C10—C9—H9	119.5	N4—C24—H24	125.3
C9—C10—C11	120.6 (2)	C24—C25—N3	106.62 (17)
C9—C10—H10	119.7	C24—C25—H25	126.7
C11—C10—H10	119.7	N3—C25—H25	126.7
C12—C11—N6	120.7 (2)	C15—N1—C16	105.85 (16)
C12—C11—C10	118.36 (17)	C15—N1—Cu1	127.69 (13)
N6—C11—C10	120.9 (2)	C16—N1—Cu1	125.30 (13)
C11—C12—C13	121.0 (2)	C15—N2—C17	107.20 (15)
C11—C12—H12	119.5	C15—N2—C18	126.28 (17)
C13—C12—H12	119.5	C17—N2—C18	126.52 (17)
C12—C13—C8	120.6 (2)	C23—N3—C25	107.03 (16)
C12—C13—H13	119.7	C23—N3—C22	126.39 (16)
C8—C13—H13	119.7	C25—N3—C22	126.51 (17)
O4—C14—O3	123.10 (17)	C23—N4—C24	105.47 (16)
O4—C14—C8	120.0 (2)	C23—N4—Cu1ii	124.79 (13)
O3—C14—C8	116.91 (18)	C24—N4—Cu1ii	129.60 (13)
N1—C15—N2	111.15 (16)	C4—N5—H5A	114 (4)
N1—C15—H15	124.4	C4—N5—H5B	116 (3)
N2—C15—H15	124.4	H5A—N5—H5B	119 (4)
C17—C16—N1	109.12 (17)	C11—N6—H6A	114 (3)
C17—C16—H16	125.4	C11—N6—H6B	116 (3)
N1—C16—H16	125.4	H6A—N6—H6B	122 (4)
C16—C17—N2	106.67 (17)	C7—O1—Cu1	108.37 (12)
C16—C17—H17	126.7	H1A—O1W—H1B	108 (3)
N2—C17—H17	126.7	C14—O3—Cu1	108.70 (12)
N2—C18—C19	111.85 (18)	H2A—O2W—H2B	105 (3)
N2—C18—H18A	109.2	H3A—O3W—H3B	99 (3)
C19—C18—H18A	109.2
C6—C1—C2—C3	1.1 (3)	N2—C15—N1—C16	0.5 (2)
C7—C1—C2—C3	179.84 (19)	N2—C15—N1—Cu1	−167.55 (13)
C1—C2—C3—C4	−1.1 (3)	C17—C16—N1—C15	−0.8 (2)
C2—C3—C4—N5	179.2 (2)	C17—C16—N1—Cu1	167.69 (14)
C2—C3—C4—C5	0.2 (3)	N4i—Cu1—N1—C15	119.0 (3)
N5—C4—C5—C6	−178.3 (2)	O3—Cu1—N1—C15	−155.13 (17)
C3—C4—C5—C6	0.7 (3)	O1—Cu1—N1—C15	16.65 (17)
C4—C5—C6—C1	−0.6 (3)	N4i—Cu1—N1—C16	−46.9 (4)
C2—C1—C6—C5	−0.2 (3)	O3—Cu1—N1—C16	38.96 (16)
C7—C1—C6—C5	−179.02 (18)	O1—Cu1—N1—C16	−149.25 (16)
C2—C1—C7—O2	172.4 (2)	N1—C15—N2—C17	−0.1 (2)
C6—C1—C7—O2	−8.8 (3)	N1—C15—N2—C18	179.02 (18)
C2—C1—C7—O1	−7.3 (3)	C16—C17—N2—C15	−0.4 (2)
C6—C1—C7—O1	171.39 (18)	C16—C17—N2—C18	−179.49 (19)
C13—C8—C9—C10	−0.4 (3)	C19—C18—N2—C15	−99.2 (2)
C14—C8—C9—C10	−179.67 (19)	C19—C18—N2—C17	79.8 (2)
C8—C9—C10—C11	−0.4 (3)	N4—C23—N3—C25	0.0 (2)
C9—C10—C11—C12	1.2 (3)	N4—C23—N3—C22	177.13 (18)
C9—C10—C11—N6	179.4 (2)	C24—C25—N3—C23	−0.5 (2)
N6—C11—C12—C13	−179.4 (2)	C24—C25—N3—C22	−177.63 (19)
C10—C11—C12—C13	−1.1 (3)	C21—C22—N3—C23	−93.1 (2)
C11—C12—C13—C8	0.3 (3)	C21—C22—N3—C25	83.5 (2)
C9—C8—C13—C12	0.5 (3)	N3—C23—N4—C24	0.5 (2)
C14—C8—C13—C12	179.72 (17)	N3—C23—N4—Cu1ii	−175.54 (12)
C9—C8—C14—O4	2.5 (3)	C25—C24—N4—C23	−0.8 (2)
C13—C8—C14—O4	−176.73 (18)	C25—C24—N4—Cu1ii	174.99 (15)
C9—C8—C14—O3	−176.92 (18)	O2—C7—O1—Cu1	9.2 (2)
C13—C8—C14—O3	3.8 (3)	C1—C7—O1—Cu1	−171.10 (13)
N1—C16—C17—N2	0.7 (2)	N4i—Cu1—O1—C7	−94.66 (13)
N2—C18—C19—C20	65.9 (2)	N1—Cu1—O1—C7	74.64 (13)
C18—C19—C20—C21	62.9 (2)	O4—C14—O3—Cu1	−9.3 (2)
C19—C20—C21—C22	63.4 (2)	C8—C14—O3—Cu1	170.13 (12)
C20—C21—C22—N3	66.3 (2)	N4i—Cu1—O3—C14	−80.43 (13)
N4—C24—C25—N3	0.8 (2)	N1—Cu1—O3—C14	110.50 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2A···O4iii	0.86 (3)	2.09 (3)	2.954 (3)	174 (4)
N5—H5A···O1Wiv	0.79 (3)	2.32 (3)	3.100 (3)	172 (5)
N6—H6B···O1Wv	0.88 (4)	2.18 (4)	3.046 (3)	170 (5)
O1W—H1A···O2W	0.86 (3)	1.95 (3)	2.805 (3)	172 (5)
O1W—H1B···O4	0.87 (3)	1.96 (3)	2.802 (2)	163 (4)
O2W—H2B···O1	0.94 (3)	2.01 (3)	2.889 (3)	155 (4)
O3W—H3A···O2	0.89 (3)	1.87 (3)	2.734 (3)	164 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2A⋯O4i	0.86 (3)	2.09 (3)	2.954 (3)	174 (4)
N5—H5A⋯O1Wii	0.79 (3)	2.32 (3)	3.100 (3)	172 (5)
N6—H6B⋯O1Wiii	0.88 (4)	2.18 (4)	3.046 (3)	170 (5)
O1W—H1A⋯O2W	0.86 (3)	1.95 (3)	2.805 (3)	172 (5)
O1W—H1B⋯O4	0.87 (3)	1.96 (3)	2.802 (2)	163 (4)
O2W—H2B⋯O1	0.94 (3)	2.01 (3)	2.889 (3)	155 (4)
O3W—H3A⋯O2	0.89 (3)	1.87 (3)	2.734 (3)	164 (4)

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