Propane-1,2-diaminium bis-(pyridine-2,6-dicarboxyl-ato-κO,N,O)cuprate(II) tetra-hydrate.

In the title compound, (C(3)H(12)N(2))[Cu(C(7)H(3)NO(4))(2)]·4H(2)O, the Cu(II) atom is six-coordinated in a distorted octa-hedral geometry by two tridentate pyridine-2,6-dicarboxyl-ate (pydc) ligands. In the crystal, inter-molecular O-H⋯O, N-H⋯O and weak C-H⋯O hydrogen bonds, as well as π-π stacking inter-actions between the pyridine rings of the pydc ligands [centroid-centroid distance = 3.4714 (14) Å] are present. C=O⋯π inter-actions between the carbonyl groups and pyridine rings [O⋯centroid distances = 3.150 (2) and 3.2233 (19) Å] are also observed.

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008d ▶). For related structures, see: Aghabozorg et al. (2008a ▶,b ▶,c ▶).

Experimental

Crystal data

(C3H12N2)[Cu(C7H3NO4)2]·4H2O

M = 541.97

Orthorhombic,

a = 20.919 (4) Å

b = 8.2015 (16) Å

c = 12.739 (3) Å

V = 2185.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.07 mm−1

T = 120 K

0.50 × 0.40 × 0.35 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T min = 0.602, T max = 0.684

9693 measured reflections

5040 independent reflections

4803 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.075

S = 1.09

5040 reflections

350 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.52 e Å−3

Absolute structure: Flack (1983 ▶), 1969 Friedel pairs

Flack parameter: −0.001 (10)

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024378/hy2413sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024378/hy2413Isup2.hkl

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

(C3H12N2)[Cu(C7H3NO4)2]·4H2O	F(000) = 1124
Mr = 541.97	Dx = 1.647 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5040 reflections
a = 20.919 (4) Å	θ = 2.5–29.1°
b = 8.2015 (16) Å	µ = 1.07 mm−1
c = 12.739 (3) Å	T = 120 K
V = 2185.6 (7) Å3	Block, blue
Z = 4	0.50 × 0.40 × 0.35 mm

Stoe IPDS-2 diffractometer	5040 independent reflections
Radiation source: fine-focus sealed tube	4803 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 29.1°, θmin = 2.5°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −24→28
Tmin = 0.602, Tmax = 0.684	k = −9→11
9693 measured reflections	l = −14→17

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0422P)2 + 0.9494P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.003
5040 reflections	Δρmax = 0.43 e Å−3
350 parameters	Δρmin = −0.52 e Å−3
7 restraints	Absolute structure: Flack (1983), 1969 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.001 (10)

	x	y	z	Uiso*/Ueq
Cu1	0.730311 (10)	0.99084 (3)	0.53964 (3)	0.00819 (6)
O1	0.65641 (8)	0.7928 (2)	0.57097 (13)	0.0156 (3)
O2	0.60721 (7)	0.67722 (19)	0.70796 (13)	0.0133 (3)
O3	0.81368 (7)	1.15817 (19)	0.58997 (13)	0.0121 (3)
O4	0.86763 (7)	1.22026 (19)	0.73603 (13)	0.0126 (3)
O5	0.65879 (7)	1.16886 (17)	0.53346 (15)	0.0134 (3)
O6	0.59524 (8)	1.2936 (2)	0.41726 (14)	0.0151 (3)
O7	0.80165 (7)	0.83190 (19)	0.48615 (13)	0.0109 (3)
O8	0.85015 (8)	0.7555 (2)	0.33667 (13)	0.0129 (3)
O9	0.56195 (10)	0.7606 (4)	0.42357 (17)	0.0426 (7)
O10	0.44108 (9)	0.8652 (2)	0.46858 (15)	0.0162 (3)
O11	0.42267 (8)	0.5941 (2)	0.59618 (14)	0.0171 (3)
O12	0.46500 (9)	0.3499 (2)	0.38944 (16)	0.0216 (4)
N1	0.73387 (8)	0.9634 (2)	0.69332 (17)	0.0079 (3)
N2	0.72136 (9)	1.0156 (2)	0.38998 (18)	0.0077 (4)
N3	0.54048 (9)	0.4390 (2)	0.59580 (16)	0.0124 (3)
N4	0.44690 (9)	0.1638 (2)	0.57235 (16)	0.0116 (4)
C1	0.64760 (10)	0.7709 (3)	0.66754 (17)	0.0096 (4)
C2	0.69142 (10)	0.8648 (2)	0.74089 (18)	0.0088 (4)
C3	0.69152 (10)	0.8437 (2)	0.84916 (18)	0.0094 (4)
H3	0.6616	0.7763	0.8813	0.011*
C4	0.73706 (10)	0.9252 (3)	0.90831 (18)	0.0112 (4)
H4	0.7382	0.9122	0.9808	0.013*
C5	0.78101 (11)	1.0265 (3)	0.85857 (19)	0.0099 (4)
H5	0.8121	1.0813	0.8971	0.012*
C6	0.77765 (10)	1.0443 (2)	0.75039 (18)	0.0079 (4)
C7	0.82336 (9)	1.1500 (2)	0.68727 (18)	0.0089 (4)
C8	0.63972 (10)	1.1994 (3)	0.44162 (19)	0.0109 (4)
C9	0.67591 (10)	1.1157 (2)	0.35435 (18)	0.0093 (4)
C10	0.66963 (11)	1.1435 (2)	0.24765 (18)	0.0110 (4)
H10	0.6379	1.2123	0.2221	0.013*
C11	0.71196 (11)	1.0660 (3)	0.17933 (17)	0.0118 (4)
H11	0.7089	1.0839	0.1074	0.014*
C12	0.75891 (11)	0.9616 (3)	0.21866 (18)	0.0097 (4)
H12	0.7875	0.9093	0.1739	0.012*
C13	0.76179 (10)	0.9379 (3)	0.32665 (17)	0.0090 (4)
C14	0.80893 (10)	0.8320 (2)	0.38701 (19)	0.0097 (4)
C15	0.53174 (11)	0.3070 (3)	0.67483 (19)	0.0135 (4)
H15B	0.5001	0.3411	0.7259	0.016*
H15A	0.5717	0.2899	0.7117	0.016*
C16	0.51050 (10)	0.1466 (2)	0.62550 (18)	0.0114 (4)
H16	0.5423	0.1141	0.5730	0.014*
C17	0.50603 (13)	0.0132 (3)	0.7083 (2)	0.0188 (5)
H17B	0.4754	0.0440	0.7607	0.023*
H17C	0.5471	−0.0017	0.7406	0.023*
H17A	0.4928	−0.0869	0.6758	0.023*
H3A	0.5597 (15)	0.404 (4)	0.538 (3)	0.023*
H4A	0.4377 (15)	0.074 (4)	0.540 (3)	0.023*
H9A	0.5887 (14)	0.790 (4)	0.468 (2)	0.023*
H10A	0.4750 (18)	0.846 (4)	0.446 (3)	0.023*
H11A	0.3889 (11)	0.562 (4)	0.572 (3)	0.023*
H12A	0.4484 (15)	0.340 (4)	0.3341 (18)	0.023*
H3B	0.4992 (17)	0.477 (4)	0.577 (3)	0.023*
H4B	0.4502 (15)	0.233 (4)	0.525 (3)	0.023*
H9B	0.5786 (16)	0.726 (4)	0.3696 (19)	0.023*
H10B	0.4158 (17)	0.830 (4)	0.421 (3)	0.023*
H11B	0.4249 (16)	0.680 (4)	0.564 (3)	0.023*
H12B	0.4996 (11)	0.316 (4)	0.372 (3)	0.023*
H3C	0.5641 (17)	0.520 (4)	0.622 (3)	0.023*
H4C	0.4190 (13)	0.200 (4)	0.613 (2)	0.023*

	U11	U22	U33	U12	U13	U23
Cu1	0.00687 (10)	0.01264 (10)	0.00506 (10)	0.00041 (8)	−0.00005 (12)	0.00104 (10)
O1	0.0129 (7)	0.0252 (8)	0.0088 (8)	−0.0069 (6)	−0.0014 (6)	−0.0002 (6)
O2	0.0105 (7)	0.0159 (7)	0.0134 (8)	−0.0052 (5)	0.0017 (6)	−0.0014 (6)
O3	0.0133 (7)	0.0152 (7)	0.0079 (8)	−0.0031 (5)	−0.0008 (6)	0.0008 (6)
O4	0.0088 (7)	0.0169 (7)	0.0122 (8)	−0.0040 (6)	−0.0002 (6)	−0.0021 (6)
O5	0.0113 (6)	0.0217 (7)	0.0072 (7)	0.0036 (5)	0.0009 (7)	0.0002 (7)
O6	0.0115 (7)	0.0202 (8)	0.0135 (8)	0.0066 (6)	−0.0001 (6)	0.0019 (6)
O7	0.0096 (7)	0.0150 (7)	0.0081 (8)	0.0023 (5)	0.0003 (6)	0.0009 (5)
O8	0.0090 (7)	0.0178 (7)	0.0120 (8)	0.0024 (6)	0.0027 (6)	0.0000 (6)
O9	0.0142 (9)	0.100 (2)	0.0136 (10)	0.0126 (11)	−0.0035 (8)	−0.0176 (12)
O10	0.0133 (8)	0.0181 (7)	0.0172 (9)	−0.0011 (6)	−0.0005 (7)	−0.0052 (6)
O11	0.0118 (7)	0.0214 (8)	0.0180 (9)	0.0024 (6)	−0.0011 (7)	0.0026 (7)
O12	0.0146 (8)	0.0367 (10)	0.0135 (9)	0.0005 (7)	−0.0046 (7)	0.0009 (7)
N1	0.0060 (8)	0.0104 (8)	0.0073 (9)	0.0005 (6)	−0.0002 (7)	0.0003 (8)
N2	0.0049 (7)	0.0120 (8)	0.0063 (9)	−0.0024 (6)	−0.0006 (7)	0.0007 (7)
N3	0.0096 (8)	0.0148 (8)	0.0128 (9)	−0.0006 (6)	−0.0004 (7)	−0.0032 (7)
N4	0.0073 (7)	0.0147 (8)	0.0128 (9)	0.0011 (6)	−0.0003 (7)	−0.0017 (7)
C1	0.0069 (8)	0.0116 (9)	0.0104 (10)	0.0006 (7)	−0.0001 (8)	0.0003 (7)
C2	0.0062 (8)	0.0097 (8)	0.0104 (10)	0.0007 (7)	−0.0001 (8)	−0.0002 (7)
C3	0.0093 (9)	0.0114 (9)	0.0074 (9)	0.0006 (7)	0.0025 (8)	0.0023 (7)
C4	0.0146 (10)	0.0142 (9)	0.0050 (9)	0.0024 (8)	0.0014 (8)	−0.0005 (7)
C5	0.0112 (9)	0.0101 (8)	0.0085 (11)	0.0025 (7)	−0.0005 (8)	−0.0015 (7)
C6	0.0073 (8)	0.0098 (8)	0.0066 (10)	0.0007 (7)	−0.0006 (7)	−0.0004 (7)
C7	0.0064 (8)	0.0090 (8)	0.0113 (10)	0.0007 (6)	0.0007 (8)	−0.0001 (7)
C8	0.0088 (9)	0.0132 (8)	0.0107 (10)	0.0000 (7)	0.0022 (8)	−0.0002 (7)
C9	0.0076 (9)	0.0117 (9)	0.0085 (9)	−0.0009 (7)	−0.0007 (8)	0.0006 (7)
C10	0.0125 (9)	0.0099 (8)	0.0105 (10)	−0.0009 (7)	0.0002 (8)	0.0009 (7)
C11	0.0156 (10)	0.0131 (9)	0.0066 (10)	−0.0028 (8)	−0.0009 (8)	−0.0004 (7)
C12	0.0116 (9)	0.0109 (8)	0.0065 (10)	−0.0032 (8)	0.0019 (8)	−0.0014 (7)
C13	0.0077 (9)	0.0097 (9)	0.0095 (11)	−0.0012 (7)	−0.0009 (8)	0.0021 (7)
C14	0.0107 (9)	0.0079 (8)	0.0105 (10)	−0.0032 (7)	−0.0005 (8)	0.0004 (7)
C15	0.0117 (9)	0.0175 (9)	0.0112 (10)	−0.0023 (8)	−0.0013 (8)	−0.0018 (8)
C16	0.0091 (9)	0.0144 (9)	0.0108 (10)	0.0000 (7)	−0.0008 (8)	−0.0015 (7)
C17	0.0220 (11)	0.0188 (10)	0.0156 (13)	0.0035 (8)	−0.0001 (10)	0.0023 (9)

Cu1—N2	1.926 (2)	N4—C16	1.499 (3)
Cu1—N1	1.972 (2)	N4—H4A	0.86 (3)
Cu1—O5	2.0920 (14)	N4—H4B	0.83 (4)
Cu1—O7	2.0953 (16)	N4—H4C	0.84 (2)
Cu1—O1	2.2775 (17)	C1—C2	1.519 (3)
Cu1—O3	2.3100 (16)	C2—C3	1.390 (3)
O1—C1	1.257 (3)	C3—C4	1.386 (3)
O2—C1	1.253 (3)	C3—H3	0.9300
O3—C7	1.258 (3)	C4—C5	1.392 (3)
O4—C7	1.255 (3)	C4—H4	0.9300
O5—C8	1.261 (3)	C5—C6	1.387 (3)
O6—C8	1.248 (3)	C5—H5	0.9300
O7—C14	1.272 (3)	C6—C7	1.521 (3)
O8—C14	1.245 (3)	C8—C9	1.510 (3)
O9—H9A	0.84 (2)	C9—C10	1.384 (3)
O9—H9B	0.82 (2)	C10—C11	1.395 (3)
O10—H10A	0.78 (4)	C10—H10	0.9300
O10—H10B	0.85 (4)	C11—C12	1.396 (3)
O11—H11A	0.82 (2)	C11—H11	0.9300
O11—H11B	0.82 (4)	C12—C13	1.390 (3)
O12—H12A	0.79 (2)	C12—H12	0.9300
O12—H12B	0.81 (2)	C13—C14	1.523 (3)
N1—C6	1.344 (3)	C15—C16	1.524 (3)
N1—C2	1.345 (3)	C15—H15B	0.9700
N2—C13	1.331 (3)	C15—H15A	0.9700
N2—C9	1.336 (3)	C16—C17	1.523 (3)
N3—C15	1.490 (3)	C16—H16	0.9800
N3—H3A	0.89 (4)	C17—H17B	0.9600
N3—H3B	0.95 (4)	C17—H17C	0.9600
N3—H3C	0.90 (4)	C17—H17A	0.9600
N2—Cu1—N1	176.55 (8)	C3—C4—H4	120.2
N2—Cu1—O5	79.62 (8)	C5—C4—H4	120.2
N1—Cu1—O5	98.27 (8)	C6—C5—C4	118.8 (2)
N2—Cu1—O7	79.21 (8)	C6—C5—H5	120.6
N1—Cu1—O7	103.00 (7)	C4—C5—H5	120.6
O5—Cu1—O7	158.64 (7)	N1—C6—C5	121.3 (2)
N2—Cu1—O1	100.52 (7)	N1—C6—C7	115.1 (2)
N1—Cu1—O1	76.72 (7)	C5—C6—C7	123.6 (2)
O5—Cu1—O1	91.08 (6)	O4—C7—O3	125.6 (2)
O7—Cu1—O1	95.55 (6)	O4—C7—C6	117.6 (2)
N2—Cu1—O3	106.59 (7)	O3—C7—C6	116.74 (18)
N1—Cu1—O3	76.33 (7)	O6—C8—O5	126.1 (2)
O5—Cu1—O3	97.80 (6)	O6—C8—C9	118.2 (2)
O7—Cu1—O3	85.54 (6)	O5—C8—C9	115.73 (19)
O1—Cu1—O3	152.56 (7)	N2—C9—C10	120.2 (2)
C1—O1—Cu1	111.91 (14)	N2—C9—C8	112.7 (2)
C7—O3—Cu1	111.32 (13)	C10—C9—C8	126.90 (19)
C8—O5—Cu1	113.56 (15)	C9—C10—C11	118.5 (2)
C14—O7—Cu1	114.06 (14)	C9—C10—H10	120.7
H9A—O9—H9B	113 (3)	C11—C10—H10	120.7
H10A—O10—H10B	104 (3)	C10—C11—C12	120.1 (2)
H11A—O11—H11B	98 (3)	C10—C11—H11	119.9
H12A—O12—H12B	97 (4)	C12—C11—H11	119.9
C6—N1—C2	120.2 (2)	C13—C12—C11	118.1 (2)
C6—N1—Cu1	120.43 (15)	C13—C12—H12	120.9
C2—N1—Cu1	119.39 (16)	C11—C12—H12	120.9
C13—N2—C9	122.7 (2)	N2—C13—C12	120.4 (2)
C13—N2—Cu1	119.20 (17)	N2—C13—C14	112.2 (2)
C9—N2—Cu1	118.04 (17)	C12—C13—C14	127.39 (19)
C15—N3—H3A	113 (2)	O8—C14—O7	126.5 (2)
C15—N3—H3B	107 (2)	O8—C14—C13	118.4 (2)
H3A—N3—H3B	108 (3)	O7—C14—C13	115.11 (19)
C15—N3—H3C	111 (2)	N3—C15—C16	112.60 (19)
H3A—N3—H3C	108 (3)	N3—C15—H15B	109.1
H3B—N3—H3C	111 (3)	C16—C15—H15B	109.1
C16—N4—H4A	109 (2)	N3—C15—H15A	109.1
C16—N4—H4B	109 (2)	C16—C15—H15A	109.1
H4A—N4—H4B	105 (3)	H15B—C15—H15A	107.8
C16—N4—H4C	112 (2)	N4—C16—C17	109.01 (18)
H4A—N4—H4C	116 (3)	N4—C16—C15	111.34 (17)
H4B—N4—H4C	106 (3)	C17—C16—C15	110.6 (2)
O2—C1—O1	126.1 (2)	N4—C16—H16	108.6
O2—C1—C2	117.73 (19)	C17—C16—H16	108.6
O1—C1—C2	116.18 (19)	C15—C16—H16	108.6
N1—C2—C3	121.4 (2)	C16—C17—H17B	109.5
N1—C2—C1	115.23 (19)	C16—C17—H17C	109.5
C3—C2—C1	123.26 (19)	H17B—C17—H17C	109.5
C4—C3—C2	118.7 (2)	C16—C17—H17A	109.5
C4—C3—H3	120.6	H17B—C17—H17A	109.5
C2—C3—H3	120.6	H17C—C17—H17A	109.5
C3—C4—C5	119.6 (2)
N2—Cu1—O1—C1	−171.17 (16)	O1—C1—C2—C3	−174.4 (2)
N1—Cu1—O1—C1	6.72 (15)	N1—C2—C3—C4	−0.8 (3)
O5—Cu1—O1—C1	−91.53 (16)	C1—C2—C3—C4	174.61 (18)
O7—Cu1—O1—C1	108.80 (15)	C2—C3—C4—C5	0.5 (3)
O3—Cu1—O1—C1	17.8 (2)	C3—C4—C5—C6	0.5 (3)
N2—Cu1—O3—C7	−179.84 (14)	C2—N1—C6—C5	1.1 (3)
N1—Cu1—O3—C7	2.05 (14)	Cu1—N1—C6—C5	−179.91 (16)
O5—Cu1—O3—C7	98.72 (14)	C2—N1—C6—C7	179.27 (18)
O7—Cu1—O3—C7	−102.50 (14)	Cu1—N1—C6—C7	−1.7 (3)
O1—Cu1—O3—C7	−9.0 (2)	C4—C5—C6—N1	−1.3 (3)
N2—Cu1—O5—C8	5.37 (15)	C4—C5—C6—C7	−179.37 (18)
N1—Cu1—O5—C8	−171.87 (15)	Cu1—O3—C7—O4	175.85 (16)
O7—Cu1—O5—C8	13.2 (3)	Cu1—O3—C7—C6	−3.5 (2)
O1—Cu1—O5—C8	−95.13 (15)	N1—C6—C7—O4	−175.73 (19)
O3—Cu1—O5—C8	110.91 (15)	C5—C6—C7—O4	2.4 (3)
N2—Cu1—O7—C14	4.09 (14)	N1—C6—C7—O3	3.6 (3)
N1—Cu1—O7—C14	−178.60 (14)	C5—C6—C7—O3	−178.2 (2)
O5—Cu1—O7—C14	−3.7 (3)	Cu1—O5—C8—O6	175.81 (18)
O1—Cu1—O7—C14	103.77 (14)	Cu1—O5—C8—C9	−5.7 (2)
O3—Cu1—O7—C14	−103.75 (15)	C13—N2—C9—C10	−0.5 (3)
O5—Cu1—N1—C6	−96.10 (17)	Cu1—N2—C9—C10	176.89 (15)
O7—Cu1—N1—C6	82.02 (18)	C13—N2—C9—C8	−175.35 (18)
O1—Cu1—N1—C6	174.75 (19)	Cu1—N2—C9—C8	2.1 (2)
O3—Cu1—N1—C6	−0.02 (16)	O6—C8—C9—N2	−178.67 (19)
O5—Cu1—N1—C2	82.93 (17)	O5—C8—C9—N2	2.7 (3)
O7—Cu1—N1—C2	−98.95 (17)	O6—C8—C9—C10	6.9 (3)
O1—Cu1—N1—C2	−6.22 (16)	O5—C8—C9—C10	−171.7 (2)
O3—Cu1—N1—C2	179.00 (18)	N2—C9—C10—C11	−0.5 (3)
O5—Cu1—N2—C13	173.65 (16)	C8—C9—C10—C11	173.5 (2)
O7—Cu1—N2—C13	−3.47 (15)	C9—C10—C11—C12	0.7 (3)
O1—Cu1—N2—C13	−97.18 (16)	C10—C11—C12—C13	0.1 (3)
O3—Cu1—N2—C13	78.52 (16)	C9—N2—C13—C12	1.4 (3)
O5—Cu1—N2—C9	−3.87 (15)	Cu1—N2—C13—C12	−176.00 (16)
O7—Cu1—N2—C9	179.02 (16)	C9—N2—C13—C14	179.81 (18)
O1—Cu1—N2—C9	85.30 (16)	Cu1—N2—C13—C14	2.4 (2)
O3—Cu1—N2—C9	−99.00 (16)	C11—C12—C13—N2	−1.2 (3)
Cu1—O1—C1—O2	175.48 (17)	C11—C12—C13—C14	−179.30 (19)
Cu1—O1—C1—C2	−6.0 (2)	Cu1—O7—C14—O8	175.91 (17)
C6—N1—C2—C3	0.0 (3)	Cu1—O7—C14—C13	−4.0 (2)
Cu1—N1—C2—C3	−179.01 (15)	N2—C13—C14—O8	−178.59 (18)
C6—N1—C2—C1	−175.74 (18)	C12—C13—C14—O8	−0.3 (3)
Cu1—N1—C2—C1	5.2 (2)	N2—C13—C14—O7	1.3 (3)
O2—C1—C2—N1	179.95 (19)	C12—C13—C14—O7	179.6 (2)
O1—C1—C2—N1	1.3 (3)	N3—C15—C16—N4	−61.9 (2)
O2—C1—C2—C3	4.3 (3)	N3—C15—C16—C17	176.67 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O11i	0.93	2.59	3.476 (3)	160
C11—H11···O7ii	0.93	2.56	3.301 (3)	137
C15—H15A···O8iii	0.97	2.30	3.245 (3)	165
C16—H16···O5iv	0.98	2.53	3.321 (3)	138
N3—H3A···O6iv	0.89 (4)	1.93 (4)	2.812 (3)	170 (3)
N3—H3B···O11	0.95 (4)	1.88 (4)	2.773 (3)	155 (3)
N3—H3C···O2	0.90 (4)	1.91 (4)	2.794 (2)	167 (4)
N4—H4A···O10iv	0.86 (3)	1.94 (3)	2.786 (3)	165 (3)
N4—H4B···O12	0.83 (4)	2.00 (4)	2.811 (3)	165 (3)
N4—H4C···O4v	0.84 (2)	2.01 (2)	2.829 (3)	167 (3)
O9—H9A···O1	0.84 (2)	1.93 (2)	2.739 (3)	163 (3)
O9—H9B···O4vi	0.82 (2)	2.04 (2)	2.826 (3)	160 (3)
O10—H10A···O9	0.78 (4)	1.97 (4)	2.731 (3)	164 (4)
O10—H10B···O8v	0.85 (4)	1.88 (4)	2.724 (3)	170 (3)
O11—H11A···O3v	0.82 (2)	2.41 (3)	3.080 (2)	140 (3)
O11—H11A···O7v	0.82 (2)	2.30 (3)	2.957 (2)	138 (3)
O11—H11B···O10	0.82 (4)	1.98 (4)	2.781 (3)	169 (3)
O12—H12A···O2vii	0.79 (2)	1.99 (2)	2.770 (3)	170 (3)
O12—H12B···O6iv	0.81 (2)	2.09 (3)	2.786 (2)	144 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O11i	0.93	2.59	3.476 (3)	160
C11—H11⋯O7ii	0.93	2.56	3.301 (3)	137
C15—H15A⋯O8iii	0.97	2.30	3.245 (3)	165
C16—H16⋯O5iv	0.98	2.53	3.321 (3)	138
N3—H3A⋯O6iv	0.89 (4)	1.93 (4)	2.812 (3)	170 (3)
N3—H3B⋯O11	0.95 (4)	1.88 (4)	2.773 (3)	155 (3)
N3—H3C⋯O2	0.90 (4)	1.91 (4)	2.794 (2)	167 (4)
N4—H4A⋯O10iv	0.86 (3)	1.94 (3)	2.786 (3)	165 (3)
N4—H4B⋯O12	0.83 (4)	2.00 (4)	2.811 (3)	165 (3)
N4—H4C⋯O4v	0.84 (2)	2.01 (2)	2.829 (3)	167 (3)
O9—H9A⋯O1	0.84 (2)	1.93 (2)	2.739 (3)	163 (3)
O9—H9B⋯O4vi	0.82 (2)	2.04 (2)	2.826 (3)	160 (3)
O10—H10A⋯O9	0.78 (4)	1.97 (4)	2.731 (3)	164 (4)
O10—H10B⋯O8v	0.85 (4)	1.88 (4)	2.724 (3)	170 (3)
O11—H11A⋯O3v	0.82 (2)	2.41 (3)	3.080 (2)	140 (3)
O11—H11A⋯O7v	0.82 (2)	2.30 (3)	2.957 (2)	138 (3)
O11—H11B⋯O10	0.82 (4)	1.98 (4)	2.781 (3)	169 (3)
O12—H12A⋯O2vii	0.79 (2)	1.99 (2)	2.770 (3)	170 (3)
O12—H12B⋯O6iv	0.81 (2)	2.09 (3)	2.786 (2)	144 (3)

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