Tris(2,2'-bipyridine)-copper(II) penta-cyanido-nitro-soferrate(II) methanol disolvate monohydrate.

The title complex [Cu(C10H8N2)3][Fe(CN)5(NO)]·2CH3OH·H2O, consists of discrete [Cu(bpy)3](2+) cations (bpy is 2,2'-bipyridine), [Fe(CN)5NO](2-) anions and solvent mol-ecules of crystallization (two methanol mol-ecules and one water mol-ecules per asymmetric unit). The Cu(II) ion adopts a distorted octa-hedral environment, coordinated by six N atoms from three bpy ligands. The cation charge is balanced by a nitro-prusside counter-anion, which has a slightly distorted octa-hedral coordination geometry. In the crystal, anions and solvent mol-ecules are involved in O-H⋯N and O-H⋯O hydrogen bonds, which form chains along [100]. The cations are located between these chains.

Related literature

For background to the direct synthesis of coordination compounds, see: Buvaylo et al. (2005 ▶); Babich et al. (1996 ▶); Kovbasyuk et al. (1998 ▶); Makhankova et al. (2002 ▶); Nesterov et al. (2006 ▶); Pryma et al. (2003 ▶); Vinogradova et al. (2002 ▶). For the structures of related complexes, see: Nikitina et al. (2008 ▶); Vreshch et al. (2009a ▶,b ▶); Shyu et al. (1997 ▶); Shyu & Wei (1999 ▶); Dong et al. (2003 ▶); Wang et al. (2007 ▶); Zhang et al. (2004 ▶).

Experimental

Crystal data

[Cu(C10H8N2)3][Fe(CN)5(NO)]·2CH4O·H2O

M = 830.15

Monoclinic,

a = 11.1308 (8) Å

b = 14.7928 (9) Å

c = 23.1448 (17) Å

β = 90.916 (8)°

V = 3810.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.00 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.74, T max = 0.91

22593 measured reflections

7368 independent reflections

3799 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.110

S = 1.01

7368 reflections

496 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.63 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006867/lh5592sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006867/lh5592Isup2.hkl

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

[Cu(C10H8N2)3][Fe(CN)5(NO)]·2CH4O·H2O	F(000) = 1708
Mr = 830.15	Dx = 1.447 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5205 reflections
a = 11.1308 (8) Å	θ = 2.6–32.2°
b = 14.7928 (9) Å	µ = 1.00 mm−1
c = 23.1448 (17) Å	T = 293 K
β = 90.916 (8)°	Block, dark red
V = 3810.4 (5) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	7368 independent reflections
Radiation source: fine-focus sealed tube	3799 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ω scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: numerical (CrysAlis PRO; Oxford Diffraction, 2010)	h = −13→11
Tmin = 0.74, Tmax = 0.91	k = −18→18
22593 measured reflections	l = −28→24

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.042P)2] where P = (Fo2 + 2Fc2)/3
7368 reflections	(Δ/σ)max = 0.001
496 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.63 e Å−3

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
Fe1	0.54777 (5)	0.85655 (4)	0.08468 (3)	0.03893 (16)
Cu1	0.91414 (4)	0.80913 (3)	0.32784 (2)	0.04640 (16)
N1	1.0220 (3)	0.7802 (2)	0.26108 (16)	0.0497 (9)
N2	1.0506 (3)	0.8936 (2)	0.34517 (16)	0.0495 (9)
N3	0.7880 (3)	0.7182 (2)	0.30682 (14)	0.0382 (8)
N4	0.9782 (3)	0.7012 (2)	0.37086 (13)	0.0378 (8)
N5	0.8102 (3)	0.8510 (2)	0.39425 (14)	0.0416 (8)
N6	0.8275 (3)	0.9133 (2)	0.29055 (14)	0.0372 (8)
N7	0.2746 (3)	0.8839 (2)	0.06854 (17)	0.0620 (11)
N8	0.5926 (3)	1.0615 (2)	0.09581 (18)	0.0622 (11)
N9	0.8113 (4)	0.8198 (3)	0.11772 (19)	0.0731 (12)
N10	0.5011 (3)	0.6536 (3)	0.10134 (18)	0.0637 (11)
N11	0.4997 (3)	0.8746 (2)	0.21488 (17)	0.0534 (10)
N12	0.5814 (3)	0.8554 (2)	0.01612 (17)	0.0492 (9)
C1	1.0021 (4)	0.7186 (3)	0.2195 (2)	0.0605 (12)
H1A	0.9292	0.6879	0.2192	0.073*
C2	1.0812 (5)	0.6988 (3)	0.1786 (2)	0.0694 (14)
H2A	1.0634	0.6554	0.1507	0.083*
C3	1.1885 (5)	0.7432 (4)	0.1783 (2)	0.0765 (16)
H3A	1.2449	0.7309	0.1501	0.092*
C4	1.2113 (4)	0.8055 (4)	0.2197 (2)	0.0739 (15)
H4A	1.2843	0.8361	0.2203	0.089*
C5	1.1273 (4)	0.8241 (3)	0.2611 (2)	0.0502 (11)
C6	1.1399 (4)	0.8914 (3)	0.3066 (2)	0.0551 (12)
C7A	0.3757 (4)	0.8748 (3)	0.07377 (18)	0.0445 (10)
C7	1.2363 (5)	0.9509 (4)	0.3111 (3)	0.0795 (16)
H7A	1.3002	0.9470	0.2858	0.095*
C8A	0.5745 (3)	0.9855 (3)	0.09130 (19)	0.0474 (11)
C8	1.2348 (5)	1.0162 (4)	0.3542 (3)	0.0928 (19)
H8A	1.2970	1.0580	0.3572	0.111*
C9A	0.7126 (4)	0.8341 (3)	0.10677 (19)	0.0474 (11)
C9	1.1436 (5)	1.0192 (4)	0.3915 (3)	0.0841 (17)
H9A	1.1416	1.0631	0.4203	0.101*
C10A	0.5162 (3)	0.7285 (3)	0.09489 (19)	0.0456 (11)
C10	1.0541 (4)	0.9564 (3)	0.3865 (2)	0.0634 (13)
H10A	0.9925	0.9576	0.4131	0.076*
C11A	0.5175 (3)	0.8666 (3)	0.1664 (2)	0.0415 (10)
C11	0.6953 (4)	0.7304 (3)	0.2706 (2)	0.0497 (11)
H11A	0.6908	0.7842	0.2499	0.060*
C12	0.6073 (4)	0.6684 (3)	0.2625 (2)	0.0546 (12)
H12A	0.5442	0.6794	0.2367	0.066*
C13	0.6126 (4)	0.5887 (3)	0.2931 (2)	0.0586 (13)
H13A	0.5521	0.5457	0.2891	0.070*
C14	0.7075 (4)	0.5742 (3)	0.32919 (19)	0.0499 (11)
H14A	0.7130	0.5207	0.3501	0.060*
C15	0.7955 (3)	0.6383 (3)	0.33483 (17)	0.0409 (10)
C16	0.9060 (4)	0.6278 (3)	0.37029 (17)	0.0413 (10)
C17	0.9377 (4)	0.5503 (3)	0.39901 (19)	0.0548 (12)
H17A	0.8866	0.5005	0.3985	0.066*
C18	1.0445 (4)	0.5465 (3)	0.4283 (2)	0.0587 (13)
H18A	1.0673	0.4940	0.4477	0.070*
C19	1.1185 (4)	0.6208 (3)	0.42895 (19)	0.0575 (12)
H19A	1.1918	0.6197	0.4487	0.069*
C20	1.0814 (4)	0.6969 (3)	0.39965 (18)	0.0476 (11)
H20A	1.1311	0.7475	0.4001	0.057*
C21	0.8078 (4)	0.8163 (3)	0.44769 (18)	0.0479 (11)
H21A	0.8631	0.7716	0.4577	0.058*
C22	0.7276 (4)	0.8438 (3)	0.48790 (19)	0.0544 (12)
H22A	0.7277	0.8176	0.5244	0.065*
C23	0.6471 (4)	0.9102 (3)	0.4740 (2)	0.0600 (12)
H23A	0.5912	0.9294	0.5008	0.072*
C24	0.6497 (4)	0.9482 (3)	0.41990 (19)	0.0535 (12)
H24A	0.5957	0.9937	0.4097	0.064*
C25	0.7321 (3)	0.9188 (2)	0.38118 (18)	0.0399 (10)
C26	0.7462 (3)	0.9554 (2)	0.32274 (18)	0.0383 (9)
C27	0.6835 (3)	1.0305 (3)	0.30261 (19)	0.0479 (11)
H27A	0.6281	1.0595	0.3259	0.058*
C28	0.7047 (4)	1.0611 (3)	0.2478 (2)	0.0556 (12)
H28A	0.6630	1.1108	0.2333	0.067*
C29	0.7865 (4)	1.0186 (3)	0.21512 (19)	0.0535 (11)
H29A	0.8024	1.0394	0.1781	0.064*
C30	0.8463 (4)	0.9441 (3)	0.23692 (18)	0.0472 (11)
H30A	0.9012	0.9143	0.2138	0.057*
O1	0.6132 (3)	0.8586 (3)	−0.03055 (15)	0.0856 (11)
O1S	0.3532 (3)	0.7337 (3)	0.3573 (2)	0.1165 (16)
H1S	0.3516	0.6904	0.3794	0.175*
C1S	0.4416 (5)	0.7904 (4)	0.3736 (3)	0.105 (2)
H1SA	0.4424	0.8416	0.3482	0.158*
H1SB	0.5173	0.7595	0.3720	0.158*
H1SC	0.4282	0.8104	0.4125	0.158*
O2S	0.0815 (7)	0.8683 (4)	0.5202 (3)	0.178 (2)
H2S	0.0561	0.8220	0.5353	0.267*
C2S	0.2053 (8)	0.8635 (5)	0.5160 (4)	0.156 (4)
H2SA	0.2349	0.9175	0.4982	0.234*
H2SB	0.2262	0.8121	0.4930	0.234*
H2SC	0.2405	0.8573	0.5540	0.234*
O3S	1.0227 (3)	0.8062 (2)	0.04880 (15)	0.0899 (11)
H3SA	1.0827	0.8365	0.0613	0.135*
H3SB	0.9690	0.8129	0.0742	0.135*

	U11	U22	U33	U12	U13	U23
Fe1	0.0380 (3)	0.0344 (3)	0.0444 (3)	0.0019 (3)	0.0002 (3)	0.0001 (3)
Cu1	0.0481 (3)	0.0407 (3)	0.0504 (3)	−0.0027 (2)	0.0019 (3)	0.0039 (3)
N1	0.045 (2)	0.045 (2)	0.059 (2)	0.0040 (17)	−0.006 (2)	0.008 (2)
N2	0.049 (2)	0.046 (2)	0.054 (2)	−0.0050 (18)	−0.011 (2)	0.014 (2)
N3	0.0303 (18)	0.0397 (18)	0.045 (2)	0.0001 (15)	−0.0026 (17)	0.0103 (17)
N4	0.0359 (19)	0.0405 (18)	0.0371 (18)	0.0027 (15)	−0.0009 (17)	0.0014 (17)
N5	0.044 (2)	0.0390 (18)	0.041 (2)	−0.0027 (16)	−0.0012 (17)	0.0017 (18)
N6	0.0386 (19)	0.0361 (17)	0.0368 (19)	−0.0056 (15)	−0.0055 (17)	0.0013 (17)
N7	0.047 (2)	0.065 (2)	0.073 (3)	0.006 (2)	−0.008 (2)	−0.007 (2)
N8	0.064 (2)	0.041 (2)	0.081 (3)	−0.0053 (19)	−0.002 (2)	0.005 (2)
N9	0.048 (2)	0.091 (3)	0.081 (3)	0.015 (2)	−0.003 (2)	−0.016 (3)
N10	0.070 (3)	0.041 (2)	0.080 (3)	−0.004 (2)	0.009 (2)	−0.004 (2)
N11	0.061 (2)	0.051 (2)	0.049 (2)	0.0053 (18)	0.004 (2)	0.005 (2)
N12	0.055 (2)	0.0411 (19)	0.051 (2)	0.0139 (18)	−0.0027 (19)	0.004 (2)
C1	0.062 (3)	0.060 (3)	0.060 (3)	0.009 (3)	0.000 (3)	0.002 (3)
C2	0.086 (4)	0.063 (3)	0.060 (3)	0.010 (3)	0.002 (3)	0.000 (3)
C3	0.089 (4)	0.077 (4)	0.065 (4)	0.017 (3)	0.023 (3)	0.013 (3)
C4	0.053 (3)	0.084 (4)	0.085 (4)	−0.006 (3)	0.009 (3)	0.028 (4)
C5	0.035 (2)	0.059 (3)	0.057 (3)	0.001 (2)	−0.001 (2)	0.021 (3)
C6	0.044 (3)	0.052 (3)	0.069 (3)	−0.011 (2)	−0.010 (3)	0.019 (3)
C7A	0.051 (3)	0.040 (2)	0.042 (2)	0.000 (2)	0.000 (2)	−0.003 (2)
C7	0.062 (3)	0.087 (4)	0.089 (4)	−0.029 (3)	−0.011 (3)	0.020 (4)
C8A	0.042 (2)	0.046 (3)	0.054 (3)	0.000 (2)	−0.001 (2)	0.009 (2)
C8	0.084 (4)	0.078 (4)	0.116 (5)	−0.043 (4)	−0.024 (4)	0.016 (4)
C9A	0.051 (3)	0.042 (2)	0.049 (3)	0.000 (2)	0.009 (2)	−0.006 (2)
C9	0.092 (4)	0.068 (3)	0.092 (4)	−0.022 (3)	−0.020 (4)	−0.003 (3)
C10A	0.039 (2)	0.045 (2)	0.053 (3)	0.006 (2)	0.001 (2)	−0.007 (2)
C10	0.065 (3)	0.054 (3)	0.071 (3)	−0.014 (3)	−0.009 (3)	0.001 (3)
C11A	0.031 (2)	0.030 (2)	0.063 (3)	0.0012 (17)	−0.001 (2)	0.004 (2)
C11	0.043 (3)	0.041 (2)	0.065 (3)	−0.004 (2)	0.002 (3)	0.009 (2)
C12	0.039 (2)	0.054 (3)	0.070 (3)	−0.006 (2)	−0.012 (2)	0.005 (3)
C13	0.051 (3)	0.044 (3)	0.080 (4)	−0.014 (2)	−0.006 (3)	−0.005 (3)
C14	0.051 (3)	0.038 (2)	0.060 (3)	−0.004 (2)	0.001 (3)	0.008 (2)
C15	0.041 (2)	0.037 (2)	0.046 (2)	−0.002 (2)	0.008 (2)	0.002 (2)
C16	0.043 (2)	0.040 (2)	0.041 (2)	0.0016 (19)	0.006 (2)	0.005 (2)
C17	0.058 (3)	0.041 (2)	0.065 (3)	−0.002 (2)	−0.001 (3)	0.012 (2)
C18	0.066 (3)	0.054 (3)	0.057 (3)	0.019 (3)	0.001 (3)	0.014 (3)
C19	0.045 (3)	0.080 (3)	0.047 (3)	0.018 (3)	−0.001 (2)	0.000 (3)
C20	0.042 (3)	0.050 (3)	0.050 (3)	0.002 (2)	−0.006 (2)	0.001 (2)
C21	0.055 (3)	0.043 (2)	0.045 (3)	−0.005 (2)	−0.003 (2)	0.006 (2)
C22	0.075 (3)	0.045 (3)	0.043 (3)	−0.015 (2)	−0.002 (3)	0.003 (2)
C23	0.077 (3)	0.052 (3)	0.052 (3)	−0.002 (3)	0.021 (3)	−0.006 (3)
C24	0.059 (3)	0.043 (2)	0.059 (3)	0.004 (2)	0.009 (3)	0.004 (2)
C25	0.044 (2)	0.033 (2)	0.044 (2)	−0.0062 (19)	0.003 (2)	−0.002 (2)
C26	0.033 (2)	0.035 (2)	0.046 (2)	−0.0043 (18)	−0.008 (2)	−0.002 (2)
C27	0.044 (2)	0.043 (2)	0.057 (3)	0.007 (2)	0.003 (2)	0.002 (2)
C28	0.054 (3)	0.046 (3)	0.066 (3)	0.005 (2)	−0.010 (3)	0.013 (3)
C29	0.060 (3)	0.053 (3)	0.047 (3)	−0.004 (2)	−0.005 (2)	0.017 (2)
C30	0.047 (3)	0.050 (3)	0.044 (3)	−0.005 (2)	0.003 (2)	0.002 (2)
O1	0.110 (3)	0.098 (3)	0.050 (2)	0.035 (2)	0.013 (2)	0.014 (2)
O1S	0.088 (3)	0.082 (3)	0.179 (5)	−0.010 (2)	−0.029 (3)	0.043 (3)
C1S	0.088 (4)	0.071 (4)	0.156 (6)	−0.005 (3)	−0.022 (4)	0.000 (4)
O2S	0.218 (6)	0.121 (4)	0.195 (6)	0.030 (5)	0.014 (6)	0.055 (4)
C2S	0.176 (8)	0.128 (6)	0.161 (8)	−0.077 (7)	−0.073 (7)	0.047 (6)
O3S	0.079 (2)	0.111 (3)	0.081 (3)	−0.002 (2)	0.013 (2)	−0.002 (2)

Fe1—N12	1.636 (4)	C11—C12	1.353 (5)
Fe1—C9A	1.926 (5)	C11—H11A	0.9300
Fe1—C11A	1.932 (5)	C12—C13	1.376 (6)
Fe1—C8A	1.936 (4)	C12—H12A	0.9300
Fe1—C10A	1.942 (5)	C13—C14	1.353 (6)
Fe1—C7A	1.947 (5)	C13—H13A	0.9300
Cu1—N3	1.999 (3)	C14—C15	1.368 (5)
Cu1—N2	2.002 (3)	C14—H14A	0.9300
Cu1—N6	2.006 (3)	C15—C16	1.476 (5)
Cu1—N4	2.006 (3)	C16—C17	1.370 (5)
Cu1—N1	2.018 (4)	C17—C18	1.360 (6)
Cu1—N5	2.035 (3)	C17—H17A	0.9300
N1—C5	1.340 (5)	C18—C19	1.374 (6)
N1—C1	1.341 (5)	C18—H18A	0.9300
N2—C10	1.333 (5)	C19—C20	1.374 (6)
N2—C6	1.347 (5)	C19—H19A	0.9300
N3—C11	1.331 (5)	C20—H20A	0.9300
N3—C15	1.349 (5)	C21—C22	1.362 (6)
N4—C20	1.321 (5)	C21—H21A	0.9300
N4—C16	1.350 (5)	C22—C23	1.364 (6)
N5—C21	1.340 (5)	C22—H22A	0.9300
N5—C25	1.359 (5)	C23—C24	1.374 (6)
N6—C26	1.336 (5)	C23—H23A	0.9300
N6—C30	1.342 (5)	C24—C25	1.364 (5)
N7—C7A	1.138 (5)	C24—H24A	0.9300
N8—C8A	1.147 (5)	C25—C26	1.467 (5)
N9—C9A	1.144 (5)	C26—C27	1.389 (5)
N10—C10A	1.130 (5)	C27—C28	1.371 (6)
N11—C11A	1.149 (5)	C27—H27A	0.9300
N12—O1	1.143 (4)	C28—C29	1.349 (6)
C1—C2	1.337 (6)	C28—H28A	0.9300
C1—H1A	0.9300	C29—C30	1.379 (5)
C2—C3	1.363 (7)	C29—H29A	0.9300
C2—H2A	0.9300	C30—H30A	0.9300
C3—C4	1.351 (7)	O1S—C1S	1.342 (6)
C3—H3A	0.9300	O1S—H1S	0.8200
C4—C5	1.377 (6)	C1S—H1SA	0.9600
C4—H4A	0.9300	C1S—H1SB	0.9600
C5—C6	1.455 (6)	C1S—H1SC	0.9602
C6—C7	1.390 (6)	O2S—C2S	1.384 (8)
C7—C8	1.389 (8)	O2S—H2S	0.8201
C7—H7A	0.9300	C2S—H2SA	0.9599
C8—C9	1.345 (8)	C2S—H2SB	0.9601
C8—H8A	0.9300	C2S—H2SC	0.9601
C9—C10	1.365 (6)	O3S—H3SA	0.8500
C9—H9A	0.9300	O3S—H3SB	0.8499
C10—H10A	0.9300
N12—Fe1—C9A	91.36 (17)	N2—C10—C9	123.3 (5)
N12—Fe1—C11A	175.03 (17)	N2—C10—H10A	118.4
C9A—Fe1—C11A	86.19 (17)	C9—C10—H10A	118.4
N12—Fe1—C8A	92.83 (18)	N11—C11A—Fe1	178.5 (4)
C9A—Fe1—C8A	90.23 (16)	N3—C11—C12	123.1 (4)
C11A—Fe1—C8A	82.87 (17)	N3—C11—H11A	118.4
N12—Fe1—C10A	98.79 (18)	C12—C11—H11A	118.4
C9A—Fe1—C10A	88.45 (16)	C11—C12—C13	119.0 (4)
C11A—Fe1—C10A	85.48 (17)	C11—C12—H12A	120.5
C8A—Fe1—C10A	168.33 (19)	C13—C12—H12A	120.5
N12—Fe1—C7A	96.65 (17)	C14—C13—C12	118.6 (4)
C9A—Fe1—C7A	171.75 (17)	C14—C13—H13A	120.7
C11A—Fe1—C7A	85.97 (16)	C12—C13—H13A	120.7
C8A—Fe1—C7A	91.33 (16)	C13—C14—C15	120.0 (4)
C10A—Fe1—C7A	88.39 (16)	C13—C14—H14A	120.0
N3—Cu1—N2	175.02 (14)	C15—C14—H14A	120.0
N3—Cu1—N6	94.69 (12)	N3—C15—C14	121.5 (4)
N2—Cu1—N6	87.97 (12)	N3—C15—C16	113.8 (3)
N3—Cu1—N4	80.07 (13)	C14—C15—C16	124.7 (4)
N2—Cu1—N4	97.75 (13)	N4—C16—C17	121.4 (4)
N6—Cu1—N4	171.67 (13)	N4—C16—C15	114.3 (3)
N3—Cu1—N1	95.46 (13)	C17—C16—C15	124.3 (4)
N2—Cu1—N1	80.02 (15)	C18—C17—C16	119.5 (4)
N6—Cu1—N1	96.94 (13)	C18—C17—H17A	120.2
N4—Cu1—N1	90.04 (12)	C16—C17—H17A	120.2
N3—Cu1—N5	89.03 (13)	C17—C18—C19	119.4 (4)
N2—Cu1—N5	95.60 (14)	C17—C18—H18A	120.3
N6—Cu1—N5	79.41 (13)	C19—C18—H18A	120.3
N4—Cu1—N5	93.94 (13)	C18—C19—C20	118.4 (4)
N1—Cu1—N5	174.46 (13)	C18—C19—H19A	120.8
C5—N1—C1	117.7 (4)	C20—C19—H19A	120.8
C5—N1—Cu1	115.4 (3)	N4—C20—C19	122.7 (4)
C1—N1—Cu1	126.8 (3)	N4—C20—H20A	118.6
C10—N2—C6	118.6 (4)	C19—C20—H20A	118.6
C10—N2—Cu1	126.3 (3)	N5—C21—C22	122.6 (4)
C6—N2—Cu1	114.7 (3)	N5—C21—H21A	118.7
C11—N3—C15	117.6 (3)	C22—C21—H21A	118.7
C11—N3—Cu1	126.6 (3)	C21—C22—C23	119.3 (4)
C15—N3—Cu1	115.8 (3)	C21—C22—H22A	120.4
C20—N4—C16	118.6 (3)	C23—C22—H22A	120.4
C20—N4—Cu1	126.0 (3)	C22—C23—C24	119.1 (4)
C16—N4—Cu1	115.4 (3)	C22—C23—H23A	120.5
C21—N5—C25	117.8 (3)	C24—C23—H23A	120.5
C21—N5—Cu1	126.9 (3)	C25—C24—C23	119.5 (4)
C25—N5—Cu1	115.2 (3)	C25—C24—H24A	120.2
C26—N6—C30	118.3 (3)	C23—C24—H24A	120.2
C26—N6—Cu1	116.3 (3)	N5—C25—C24	121.6 (4)
C30—N6—Cu1	125.3 (3)	N5—C25—C26	113.6 (3)
O1—N12—Fe1	174.4 (4)	C24—C25—C26	124.8 (4)
C2—C1—N1	123.6 (5)	N6—C26—C27	121.8 (4)
C2—C1—H1A	118.2	N6—C26—C25	115.2 (3)
N1—C1—H1A	118.2	C27—C26—C25	123.0 (4)
C1—C2—C3	119.1 (5)	C28—C27—C26	118.8 (4)
C1—C2—H2A	120.5	C28—C27—H27A	120.6
C3—C2—H2A	120.5	C26—C27—H27A	120.6
C4—C3—C2	118.7 (5)	C29—C28—C27	119.5 (4)
C4—C3—H3A	120.7	C29—C28—H28A	120.2
C2—C3—H3A	120.7	C27—C28—H28A	120.2
C3—C4—C5	120.5 (5)	C28—C29—C30	119.6 (4)
C3—C4—H4A	119.7	C28—C29—H29A	120.2
C5—C4—H4A	119.7	C30—C29—H29A	120.2
N1—C5—C4	120.5 (5)	N6—C30—C29	121.9 (4)
N1—C5—C6	113.9 (4)	N6—C30—H30A	119.0
C4—C5—C6	125.6 (5)	C29—C30—H30A	119.0
N2—C6—C7	120.9 (5)	C1S—O1S—H1S	109.6
N2—C6—C5	115.6 (4)	O1S—C1S—H1SA	109.6
C7—C6—C5	123.5 (5)	O1S—C1S—H1SB	109.4
N7—C7A—Fe1	178.1 (4)	H1SA—C1S—H1SB	109.5
C8—C7—C6	118.4 (5)	O1S—C1S—H1SC	109.4
C8—C7—H7A	120.8	H1SA—C1S—H1SC	109.5
C6—C7—H7A	120.8	H1SB—C1S—H1SC	109.5
N8—C8A—Fe1	178.6 (4)	C2S—O2S—H2S	109.7
C9—C8—C7	120.2 (5)	O2S—C2S—H2SA	109.7
C9—C8—H8A	119.9	O2S—C2S—H2SB	109.3
C7—C8—H8A	119.9	H2SA—C2S—H2SB	109.5
N9—C9A—Fe1	177.3 (4)	O2S—C2S—H2SC	109.4
C8—C9—C10	118.7 (6)	H2SA—C2S—H2SC	109.5
C8—C9—H9A	120.7	H2SB—C2S—H2SC	109.5
C10—C9—H9A	120.7	H3SA—O3S—H3SB	105.2
N10—C10A—Fe1	178.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3S—H3SB···N9	0.85	2.04	2.870 (5)	165
O3S—H3SA···N7i	0.85	2.25	3.058 (5)	158
O1S—H1S···N8ii	0.82	2.08	2.831 (5)	151
O2S—H2S···O3Siii	0.82	1.96	2.746 (7)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3S—H3SB⋯N9	0.85	2.04	2.870 (5)	165
O3S—H3SA⋯N7i	0.85	2.25	3.058 (5)	158
O1S—H1S⋯N8ii	0.82	2.08	2.831 (5)	151
O2S—H2S⋯O3S iii	0.82	1.96	2.746 (7)	161

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