μ-α-Methyl-glutarato-bis-{aqua-[bis-(2-pyridylcarbon-yl)aminato]copper(II)} trihydrate.

In the title compound, [Cu(2)(C(12)H(8)N(3)O(2))(2)(C(6)H(8)O(4))(H(2)O)(2)]·3H(2)O, both crystallographically independent Cu atoms are in similar distorted square-pyramidal coordination environments. The dinuclear complex mol-ecules are assembled into one-dimensional supra-molecular chains extending in the [100] direction by hydrogen bonds. Inter-chain hydrogen bonds further link these chains into layers perpendicular to [001].

Related literature

For general background, see: Kajiwara et al. (2002 ▶); Kamiyama et al. (2000 ▶); Kooijman et al. (2006 ▶); Lescouezec et al. (2005 ▶); Ohkoshi & Hashimoto (1999 ▶); Ohkoshi et al. (1998 ▶); Smolin & Rapoport (1959 ▶); Toma et al. (2005 ▶); Yamamoto et al. (1998 ▶); Zheng et al. (2006 ▶). For related structures, see: Wei et al. (2002 ▶).

Experimental

Crystal data

[Cu2(C12H8N3O2)2(C6H8O4)(H2O)2]·3H2O

M = 813.71

Orthorhombic,

a = 7.2712 (15) Å

b = 26.910 (5) Å

c = 34.207 (7) Å

V = 6693 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.35 mm−1

T = 293 (2) K

0.31 × 0.28 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.502, T max = 0.547 (expected range = 0.720–0.785)

55287 measured reflections

7670 independent reflections

5714 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.05

7670 reflections

461 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.26 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034570/cs2084sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034570/cs2084Isup2.hkl

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

[Cu2(C12H8N3O2)2(C6H8O4)(H2O)2]·3H2O	F(000) = 3344
Mr = 813.71	Dx = 1.615 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 37378 reflections
a = 7.2712 (15) Å	θ = 3.0–27.5°
b = 26.910 (5) Å	µ = 1.35 mm−1
c = 34.207 (7) Å	T = 293 K
V = 6693 (2) Å3	Prism, blue
Z = 8	0.31 × 0.28 × 0.18 mm

Rigaku R-AXIS RAPID diffractometer	7670 independent reflections
Radiation source: fine-focus sealed tube	5714 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −34→34
Tmin = 0.502, Tmax = 0.547	l = −37→44
55287 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0539P)2 + 2.9935P] where P = (Fo2 + 2Fc2)/3
7670 reflections	(Δ/σ)max = 0.001
461 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.54934 (4)	0.175121 (11)	0.399089 (8)	0.03535 (9)
Cu2	0.53997 (4)	0.428788 (12)	0.359585 (9)	0.03870 (10)
N1	0.6355 (3)	0.39906 (8)	0.30992 (6)	0.0419 (5)
N2	0.5980 (3)	0.49025 (8)	0.33255 (6)	0.0419 (5)
N3	0.4645 (3)	0.47635 (8)	0.40161 (6)	0.0407 (5)
N4	0.6124 (3)	0.22696 (8)	0.43940 (6)	0.0390 (5)
N5	0.5884 (3)	0.13085 (8)	0.44302 (6)	0.0406 (5)
N6	0.4822 (3)	0.11127 (8)	0.37233 (6)	0.0373 (5)
O1	0.6058 (3)	0.57559 (7)	0.34103 (6)	0.0569 (5)
O2	0.7173 (4)	0.51996 (9)	0.27399 (6)	0.0710 (7)
O3	0.8095 (3)	0.40705 (9)	0.38851 (6)	0.0580 (5)
H3A	0.9077	0.3911	0.3792	0.070*
H3B	0.8148	0.4194	0.4104	0.070*
O4	0.4229 (2)	0.36961 (7)	0.38088 (6)	0.0455 (4)
O5	0.1669 (3)	0.40030 (7)	0.35585 (6)	0.0520 (5)
O6	0.8389 (3)	0.17044 (8)	0.37424 (7)	0.0631 (6)
H6A	0.9344	0.1804	0.3830	0.076*
H6B	0.8544	0.1431	0.3642	0.076*
O7	0.4551 (2)	0.22091 (7)	0.35979 (5)	0.0422 (4)
O8	0.1987 (3)	0.20334 (8)	0.39062 (6)	0.0545 (5)
O9	0.6702 (4)	0.13072 (8)	0.50887 (6)	0.0742 (7)
O10	0.6010 (3)	0.04711 (7)	0.45907 (6)	0.0548 (5)
O11	−0.1837 (5)	0.12871 (10)	0.26137 (10)	0.1035 (10)
H11B	−0.1864	0.1000	0.2754	0.124*
H11A	−0.2408	0.1608	0.2588	0.124*
O12	−0.1091 (4)	0.43917 (9)	0.46254 (6)	0.0694 (6)
H12A	−0.0701	0.4702	0.4636	0.083*
H12B	−0.0190	0.4245	0.4753	0.083*
O13	−0.3775 (4)	0.21512 (10)	0.28183 (7)	0.0788 (7)
H13A	−0.4803	0.2103	0.2712	0.095*
H13B	−0.4091	0.2186	0.3047	0.095*
C1	0.6535 (4)	0.35111 (11)	0.30126 (9)	0.0494 (7)
H1	0.6177	0.3276	0.3197	0.059*
C2	0.7233 (4)	0.33506 (13)	0.26606 (9)	0.0587 (8)
H2	0.7339	0.3013	0.2606	0.070*
C3	0.7770 (5)	0.37017 (14)	0.23906 (9)	0.0634 (9)
H3	0.8245	0.3603	0.2150	0.076*
C4	0.7601 (4)	0.41966 (13)	0.24782 (8)	0.0560 (8)
H4	0.7956	0.4437	0.2298	0.067*
C5	0.6896 (4)	0.43331 (11)	0.28384 (7)	0.0427 (6)
C6	0.6701 (4)	0.48686 (11)	0.29562 (8)	0.0461 (6)
C7	0.5733 (3)	0.53352 (10)	0.35210 (8)	0.0424 (6)
C8	0.4951 (3)	0.52436 (10)	0.39251 (8)	0.0405 (6)
C9	0.4558 (4)	0.56223 (12)	0.41808 (9)	0.0536 (7)
H9	0.4785	0.5951	0.4113	0.064*
C10	0.3814 (5)	0.55019 (13)	0.45422 (9)	0.0592 (8)
H10	0.3533	0.5751	0.4721	0.071*
C11	0.3496 (4)	0.50144 (13)	0.46335 (8)	0.0569 (8)
H11	0.2997	0.4928	0.4875	0.068*
C12	0.3924 (4)	0.46541 (12)	0.43645 (8)	0.0498 (7)
H12	0.3705	0.4323	0.4427	0.060*
C13	0.2503 (4)	0.36850 (9)	0.37466 (7)	0.0383 (6)
C14	0.1458 (4)	0.32513 (10)	0.39196 (8)	0.0464 (6)
H14A	0.0544	0.3376	0.4101	0.056*
H14B	0.2305	0.3043	0.4065	0.056*
C15	0.0508 (4)	0.29403 (10)	0.36086 (9)	0.0495 (7)
H15A	−0.0378	0.2722	0.3733	0.059*
H15B	−0.0155	0.3158	0.3432	0.059*
C16	0.1865 (4)	0.26321 (11)	0.33775 (8)	0.0454 (6)
H16	0.2791	0.2855	0.3266	0.054*
C17	0.2841 (4)	0.22620 (10)	0.36493 (7)	0.0401 (6)
C18	0.0964 (5)	0.23415 (14)	0.30441 (10)	0.0677 (9)
H18A	0.1890	0.2161	0.2903	0.081*
H18B	0.0355	0.2568	0.2870	0.081*
H18C	0.0083	0.2112	0.3150	0.081*
C19	0.6176 (4)	0.27655 (10)	0.43521 (8)	0.0469 (6)
H19	0.5975	0.2902	0.4106	0.056*
C20	0.6518 (5)	0.30785 (11)	0.46620 (10)	0.0591 (8)
H20	0.6551	0.3421	0.4625	0.071*
C21	0.6809 (5)	0.28799 (12)	0.50268 (9)	0.0613 (8)
H21	0.7008	0.3085	0.5241	0.074*
C22	0.6800 (4)	0.23712 (12)	0.50692 (8)	0.0546 (7)
H22	0.7025	0.2229	0.5312	0.065*
C23	0.6456 (4)	0.20759 (10)	0.47502 (7)	0.0428 (6)
C24	0.6377 (4)	0.15139 (10)	0.47802 (8)	0.0459 (6)
C25	0.5724 (3)	0.08108 (10)	0.43633 (8)	0.0392 (6)
C26	0.5099 (3)	0.07091 (9)	0.39491 (7)	0.0362 (5)
C27	0.4783 (4)	0.02377 (10)	0.38124 (8)	0.0446 (6)
H27	0.4976	−0.0036	0.3973	0.054*
C28	0.4175 (4)	0.01755 (11)	0.34332 (9)	0.0503 (7)
H28	0.3970	−0.0142	0.3334	0.060*
C29	0.3879 (4)	0.05820 (11)	0.32057 (9)	0.0518 (7)
H29	0.3450	0.0547	0.2951	0.062*
C30	0.4223 (4)	0.10465 (10)	0.33579 (8)	0.0460 (6)
H30	0.4032	0.1324	0.3201	0.055*

	U11	U22	U33	U12	U13	U23
Cu1	0.04081 (18)	0.03272 (16)	0.03252 (16)	0.00093 (12)	−0.00488 (13)	0.00500 (12)
Cu2	0.03813 (18)	0.03853 (18)	0.03945 (17)	−0.00216 (13)	0.00413 (13)	0.00180 (13)
N1	0.0352 (11)	0.0474 (13)	0.0429 (12)	−0.0011 (10)	−0.0028 (9)	−0.0040 (10)
N2	0.0423 (12)	0.0409 (12)	0.0424 (11)	−0.0042 (10)	0.0038 (10)	0.0018 (10)
N3	0.0343 (11)	0.0438 (12)	0.0441 (12)	0.0003 (9)	0.0023 (9)	0.0013 (10)
N4	0.0388 (11)	0.0392 (11)	0.0390 (11)	−0.0006 (9)	−0.0043 (9)	0.0026 (9)
N5	0.0498 (13)	0.0361 (11)	0.0358 (11)	−0.0021 (9)	−0.0064 (10)	0.0069 (9)
N6	0.0378 (11)	0.0363 (11)	0.0378 (11)	−0.0002 (9)	−0.0003 (9)	0.0045 (9)
O1	0.0696 (14)	0.0403 (11)	0.0607 (12)	−0.0068 (10)	0.0064 (11)	0.0039 (9)
O2	0.0964 (18)	0.0621 (14)	0.0544 (12)	−0.0039 (13)	0.0194 (13)	0.0150 (11)
O3	0.0429 (11)	0.0751 (14)	0.0562 (12)	0.0099 (10)	−0.0059 (9)	−0.0121 (11)
O4	0.0365 (10)	0.0407 (10)	0.0594 (12)	0.0002 (8)	0.0034 (9)	0.0073 (9)
O5	0.0456 (11)	0.0405 (10)	0.0699 (13)	0.0011 (9)	−0.0042 (10)	0.0123 (9)
O6	0.0454 (12)	0.0494 (12)	0.0944 (17)	−0.0048 (9)	0.0140 (12)	−0.0135 (11)
O7	0.0443 (10)	0.0427 (10)	0.0395 (9)	0.0084 (8)	−0.0055 (8)	0.0053 (8)
O8	0.0469 (11)	0.0563 (12)	0.0601 (12)	0.0039 (10)	−0.0005 (10)	0.0112 (10)
O9	0.120 (2)	0.0585 (13)	0.0436 (11)	−0.0118 (14)	−0.0271 (13)	0.0149 (10)
O10	0.0743 (14)	0.0414 (11)	0.0487 (11)	−0.0025 (10)	−0.0117 (10)	0.0150 (9)
O11	0.128 (3)	0.0629 (17)	0.120 (2)	0.0112 (17)	0.010 (2)	0.0282 (16)
O12	0.0928 (18)	0.0621 (14)	0.0531 (12)	0.0024 (13)	−0.0098 (12)	−0.0001 (11)
O13	0.0754 (16)	0.100 (2)	0.0607 (14)	−0.0013 (15)	0.0081 (12)	0.0096 (14)
C1	0.0420 (15)	0.0497 (16)	0.0565 (16)	−0.0013 (13)	−0.0056 (13)	−0.0061 (13)
C2	0.0512 (17)	0.063 (2)	0.0615 (19)	0.0038 (15)	−0.0064 (15)	−0.0207 (16)
C3	0.0538 (18)	0.086 (3)	0.0502 (17)	0.0043 (17)	−0.0012 (15)	−0.0222 (17)
C4	0.0498 (16)	0.080 (2)	0.0383 (14)	−0.0017 (16)	0.0020 (13)	−0.0009 (15)
C5	0.0353 (13)	0.0568 (16)	0.0360 (12)	−0.0018 (12)	−0.0035 (11)	0.0009 (12)
C6	0.0408 (14)	0.0555 (17)	0.0421 (14)	−0.0031 (12)	0.0004 (12)	0.0079 (13)
C7	0.0344 (13)	0.0439 (15)	0.0489 (15)	−0.0047 (11)	0.0003 (11)	0.0006 (12)
C8	0.0312 (12)	0.0464 (15)	0.0440 (14)	−0.0023 (11)	−0.0009 (10)	−0.0019 (12)
C9	0.0493 (17)	0.0514 (17)	0.0601 (18)	−0.0007 (13)	0.0030 (14)	−0.0114 (14)
C10	0.0567 (18)	0.068 (2)	0.0533 (17)	0.0021 (16)	0.0031 (15)	−0.0180 (16)
C11	0.0513 (17)	0.079 (2)	0.0404 (14)	0.0042 (16)	0.0073 (13)	−0.0023 (15)
C12	0.0474 (15)	0.0566 (17)	0.0455 (15)	0.0016 (13)	0.0048 (13)	0.0056 (13)
C13	0.0440 (14)	0.0319 (13)	0.0388 (13)	0.0017 (11)	0.0061 (11)	−0.0013 (10)
C14	0.0473 (15)	0.0421 (15)	0.0496 (15)	−0.0018 (12)	0.0071 (13)	0.0056 (12)
C15	0.0400 (15)	0.0373 (14)	0.071 (2)	−0.0006 (12)	−0.0042 (14)	0.0079 (13)
C16	0.0416 (14)	0.0508 (16)	0.0438 (14)	−0.0005 (12)	−0.0076 (12)	0.0048 (12)
C17	0.0474 (15)	0.0376 (13)	0.0354 (12)	0.0008 (12)	−0.0051 (12)	−0.0009 (11)
C18	0.075 (2)	0.076 (2)	0.0524 (18)	−0.0053 (19)	−0.0135 (17)	0.0037 (17)
C19	0.0488 (15)	0.0430 (15)	0.0490 (15)	0.0003 (12)	−0.0070 (13)	0.0048 (12)
C20	0.066 (2)	0.0412 (16)	0.070 (2)	−0.0052 (14)	−0.0114 (17)	−0.0046 (14)
C21	0.071 (2)	0.0567 (19)	0.0564 (18)	−0.0087 (16)	−0.0156 (16)	−0.0119 (15)
C22	0.0607 (19)	0.0628 (19)	0.0402 (14)	−0.0070 (15)	−0.0134 (14)	−0.0012 (13)
C23	0.0436 (15)	0.0456 (15)	0.0391 (13)	−0.0039 (12)	−0.0060 (11)	0.0033 (11)
C24	0.0533 (16)	0.0468 (15)	0.0377 (13)	−0.0045 (13)	−0.0078 (12)	0.0079 (12)
C25	0.0361 (13)	0.0393 (13)	0.0421 (13)	−0.0007 (10)	0.0002 (11)	0.0078 (11)
C26	0.0307 (12)	0.0380 (13)	0.0400 (13)	−0.0010 (10)	0.0047 (10)	0.0047 (11)
C27	0.0493 (15)	0.0344 (13)	0.0502 (15)	−0.0023 (12)	0.0051 (13)	0.0052 (12)
C28	0.0556 (17)	0.0411 (15)	0.0541 (16)	−0.0073 (13)	0.0039 (14)	−0.0068 (13)
C29	0.0605 (18)	0.0534 (17)	0.0417 (14)	−0.0065 (14)	−0.0039 (14)	−0.0052 (13)
C30	0.0586 (17)	0.0401 (14)	0.0392 (14)	−0.0010 (13)	−0.0059 (12)	0.0041 (12)

Cu1—N5	1.939 (2)	C3—H3	0.9300
Cu1—O7	1.9479 (17)	C4—C5	1.384 (4)
Cu1—N6	2.007 (2)	C4—H4	0.9300
Cu1—N4	2.014 (2)	C5—C6	1.503 (4)
Cu1—O6	2.274 (2)	C7—C8	1.515 (4)
Cu2—N2	1.941 (2)	C8—C9	1.373 (4)
Cu2—O4	1.9470 (19)	C9—C10	1.388 (4)
Cu2—N3	2.001 (2)	C9—H9	0.9300
Cu2—N1	2.002 (2)	C10—C11	1.368 (5)
Cu2—O3	2.272 (2)	C10—H10	0.9300
N1—C1	1.330 (4)	C11—C12	1.373 (4)
N1—C5	1.342 (3)	C11—H11	0.9300
N2—C7	1.355 (3)	C12—H12	0.9300
N2—C6	1.371 (3)	C13—C14	1.513 (4)
N3—C12	1.335 (3)	C14—C15	1.520 (4)
N3—C8	1.347 (4)	C14—H14A	0.9700
N4—C19	1.342 (3)	C14—H14B	0.9700
N4—C23	1.347 (3)	C15—C16	1.512 (4)
N5—C25	1.364 (3)	C15—H15A	0.9700
N5—C24	1.366 (3)	C15—H15B	0.9700
N6—C30	1.336 (3)	C16—C18	1.530 (4)
N6—C26	1.348 (3)	C16—C17	1.536 (4)
O1—C7	1.217 (3)	C16—H16	0.9800
O2—C6	1.208 (3)	C18—H18A	0.9600
O3—H3A	0.8924	C18—H18B	0.9600
O3—H3B	0.8203	C18—H18C	0.9600
O4—C13	1.274 (3)	C19—C20	1.376 (4)
O5—C13	1.230 (3)	C19—H19	0.9300
O6—H6A	0.8019	C20—C21	1.374 (4)
O6—H6B	0.8200	C20—H20	0.9300
O7—C17	1.264 (3)	C21—C22	1.377 (4)
O8—C17	1.239 (3)	C21—H21	0.9300
O9—C24	1.216 (3)	C22—C23	1.373 (4)
O10—C25	1.218 (3)	C22—H22	0.9300
O11—H11B	0.9101	C23—C24	1.517 (4)
O11—H11A	0.9623	C25—C26	1.513 (4)
O12—H12A	0.8813	C26—C27	1.371 (4)
O12—H12B	0.8800	C27—C28	1.380 (4)
O13—H13A	0.8412	C27—H27	0.9300
O13—H13B	0.8222	C28—C29	1.360 (4)
C1—C2	1.376 (4)	C28—H28	0.9300
C1—H1	0.9300	C29—C30	1.377 (4)
C2—C3	1.378 (5)	C29—H29	0.9300
C2—H2	0.9300	C30—H30	0.9300
C3—C4	1.370 (5)
N5—Cu1—O7	167.20 (9)	C11—C10—C9	119.5 (3)
N5—Cu1—N6	82.13 (9)	C11—C10—H10	120.2
O7—Cu1—N6	98.13 (8)	C9—C10—H10	120.2
N5—Cu1—N4	82.04 (9)	C10—C11—C12	119.1 (3)
O7—Cu1—N4	96.56 (8)	C10—C11—H11	120.5
N6—Cu1—N4	163.82 (8)	C12—C11—H11	120.5
N5—Cu1—O6	96.91 (9)	N3—C12—C11	122.1 (3)
O7—Cu1—O6	95.88 (8)	N3—C12—H12	118.9
N6—Cu1—O6	90.41 (8)	C11—C12—H12	118.9
N4—Cu1—O6	94.80 (8)	O5—C13—O4	123.8 (2)
N2—Cu2—O4	165.95 (9)	O5—C13—C14	119.6 (2)
N2—Cu2—N3	81.77 (9)	O4—C13—C14	116.6 (2)
O4—Cu2—N3	97.74 (9)	C13—C14—C15	112.3 (2)
N2—Cu2—N1	82.00 (9)	C13—C14—H14A	109.1
O4—Cu2—N1	98.17 (9)	C15—C14—H14A	109.1
N3—Cu2—N1	163.76 (9)	C13—C14—H14B	109.1
N2—Cu2—O3	103.84 (9)	C15—C14—H14B	109.1
O4—Cu2—O3	90.20 (8)	H14A—C14—H14B	107.9
N3—Cu2—O3	95.07 (8)	C16—C15—C14	111.8 (2)
N1—Cu2—O3	88.13 (8)	C16—C15—H15A	109.3
C1—N1—C5	119.3 (2)	C14—C15—H15A	109.3
C1—N1—Cu2	127.6 (2)	C16—C15—H15B	109.3
C5—N1—Cu2	113.05 (18)	C14—C15—H15B	109.3
C7—N2—C6	124.2 (2)	H15A—C15—H15B	107.9
C7—N2—Cu2	117.93 (17)	C15—C16—C18	113.0 (3)
C6—N2—Cu2	117.74 (18)	C15—C16—C17	109.9 (2)
C12—N3—C8	118.8 (2)	C18—C16—C17	108.5 (2)
C12—N3—Cu2	127.4 (2)	C15—C16—H16	108.4
C8—N3—Cu2	113.71 (17)	C18—C16—H16	108.4
C19—N4—C23	118.4 (2)	C17—C16—H16	108.4
C19—N4—Cu1	128.44 (18)	O8—C17—O7	122.4 (2)
C23—N4—Cu1	113.08 (17)	O8—C17—C16	121.3 (2)
C25—N5—C24	124.5 (2)	O7—C17—C16	116.3 (2)
C25—N5—Cu1	117.44 (17)	C16—C18—H18A	109.5
C24—N5—Cu1	117.98 (17)	C16—C18—H18B	109.5
C30—N6—C26	118.5 (2)	H18A—C18—H18B	109.5
C30—N6—Cu1	128.33 (18)	C16—C18—H18C	109.5
C26—N6—Cu1	113.10 (17)	H18A—C18—H18C	109.5
Cu2—O3—H3A	131.2	H18B—C18—H18C	109.5
Cu2—O3—H3B	109.5	N4—C19—C20	122.1 (3)
H3A—O3—H3B	118.9	N4—C19—H19	119.0
C13—O4—Cu2	112.80 (16)	C20—C19—H19	119.0
Cu1—O6—H6A	130.1	C21—C20—C19	119.3 (3)
Cu1—O6—H6B	109.5	C21—C20—H20	120.4
H6A—O6—H6B	109.6	C19—C20—H20	120.4
C17—O7—Cu1	108.74 (16)	C20—C21—C22	118.8 (3)
H11B—O11—H11A	143.2	C20—C21—H21	120.6
H12A—O12—H12B	99.4	C22—C21—H21	120.6
H13A—O13—H13B	100.4	C23—C22—C21	119.5 (3)
N1—C1—C2	122.4 (3)	C23—C22—H22	120.2
N1—C1—H1	118.8	C21—C22—H22	120.2
C2—C1—H1	118.8	N4—C23—C22	121.9 (3)
C1—C2—C3	118.4 (3)	N4—C23—C24	116.1 (2)
C1—C2—H2	120.8	C22—C23—C24	122.0 (2)
C3—C2—H2	120.8	O9—C24—N5	128.8 (3)
C4—C3—C2	119.6 (3)	O9—C24—C23	120.5 (3)
C4—C3—H3	120.2	N5—C24—C23	110.7 (2)
C2—C3—H3	120.2	O10—C25—N5	128.0 (3)
C3—C4—C5	119.0 (3)	O10—C25—C26	120.9 (2)
C3—C4—H4	120.5	N5—C25—C26	111.1 (2)
C5—C4—H4	120.5	N6—C26—C27	121.7 (2)
N1—C5—C4	121.2 (3)	N6—C26—C25	115.8 (2)
N1—C5—C6	116.9 (2)	C27—C26—C25	122.5 (2)
C4—C5—C6	121.9 (3)	C26—C27—C28	119.1 (3)
O2—C6—N2	128.6 (3)	C26—C27—H27	120.5
O2—C6—C5	121.1 (3)	C28—C27—H27	120.5
N2—C6—C5	110.3 (2)	C29—C28—C27	119.4 (3)
O1—C7—N2	128.3 (3)	C29—C28—H28	120.3
O1—C7—C8	120.5 (3)	C27—C28—H28	120.3
N2—C7—C8	111.1 (2)	C28—C29—C30	119.0 (3)
N3—C8—C9	122.0 (3)	C28—C29—H29	120.5
N3—C8—C7	115.4 (2)	C30—C29—H29	120.5
C9—C8—C7	122.6 (3)	N6—C30—C29	122.3 (3)
C8—C9—C10	118.4 (3)	N6—C30—H30	118.9
C8—C9—H9	120.8	C29—C30—H30	118.9
C10—C9—H9	120.8

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5i	0.89	2.06	2.835 (4)	144
O3—H3B···O12i	0.82	1.94	2.740 (4)	164
O6—H6A···O8i	0.80	2.04	2.819 (4)	165
O6—H6B···O1ii	0.82	2.00	2.822 (4)	179
O11—H11A···O13	0.962	1.94	2.808 (4)	150
O11—H11B···O2iii	0.910	2.17	2.968 (4)	146
O11—H11B···O1iii	0.910	2.41	3.129 (4)	136
O12—H12A···O10iv	0.88	2.09	2.907 (4)	154
O12—H12B···O9v	0.88	2.10	2.935 (4)	159
O12—H12B···O10v	0.88	2.53	3.108 (4)	124
O13—H13B···O7vi	0.820	2.13	2.933 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O5i	0.89	2.06	2.835 (4)	144
O3—H3B⋯O12i	0.82	1.94	2.740 (4)	164
O6—H6A⋯O8i	0.80	2.04	2.819 (4)	165
O6—H6B⋯O1ii	0.82	2.00	2.822 (4)	179
O11—H11A⋯O13	0.962	1.94	2.808 (4)	150
O11—H11B⋯O2iii	0.910	2.17	2.968 (4)	146
O11—H11B⋯O1iii	0.910	2.41	3.129 (4)	136
O12—H12A⋯O10iv	0.88	2.09	2.907 (4)	154
O12—H12B⋯O9v	0.88	2.10	2.935 (4)	159
O12—H12B⋯O10v	0.88	2.53	3.108 (4)	124
O13—H13B⋯O7vi	0.820	2.13	2.933 (4)	168

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