Tris(1,10-phenanthrolin-1-ium) hexa-cyanidoferrate(III) ethanol monosolvate trihydrate.

The asymmetric unit of the title complex, (C(12)H(9)N(2))(3)[Fe(CN)(6)]·C(2)H(5)OH·3H(2)O, consists of two half [Fe(CN)(6)](3-) anions located on inversion centers, three 1,10-phenanthrolin-1-ium cations, [Hphen](+), an ethanol and three water solvent mol-ecules. The average Fe-C and C-N bond lengths are 1.942 (6) and 1.154 (3) Å, respectively, while the Fe-C-N angles deviate slightly from linearity with values ranging from 177.8 (2) to 179.7 (2)°. The Fe(III) atoms adopt a distorted octa-hedral geometry. All the species are linked through O-H⋯N, N-H⋯O and O-H⋯O hydrogen-bonding inter-actions, resulting in a three-dimensional supra-molecular network.

Related literature

For general background to hexa­cyanido­metalate(III)-based complexes, see: Andruh et al. (2009 ▶); Tokoro & Ohkoshi (2011 ▶). For background to complexes containing hexa­cyanido­metalate and phen ligands, see: Koner et al. (2005 ▶).

Experimental

Crystal data

(C12H9N2)3[n class="Chemical">Fe(CN)6]·C2H6O·3H2O

M = 855.72

Monoclinic,

a = 20.5744 (18) Å

b = 14.8742 (13) Å

c = 14.1594 (12) Å

β = 109.123 (1)°

V = 4094.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 173 K

0.21 × 0.18 × 0.16 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.915, T max = 0.935

35350 measured reflections

9412 independent reflections

6179 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.01

9412 reflections

555 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: n class="Chemical">contains datablock(s) I, global. DOI: 10.1107/S1600536812017990/pv2532sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017990/pv2532Isup2.hkl

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

(C12H9N2)3[Fe(CN)6]·C2H6O·3H2O	F(000) = 1780
Mr = 855.72	Dx = 1.388 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6253 reflections
a = 20.5744 (18) Å	θ = 2.5–27.4°
b = 14.8742 (13) Å	µ = 0.43 mm−1
c = 14.1594 (12) Å	T = 173 K
β = 109.123 (1)°	Block, colorless
V = 4094.1 (6) Å3	0.21 × 0.18 × 0.16 mm
Z = 4

Bruker APEXII diffractometer	9412 independent reflections
Radiation source: fine-focus sealed tube	6179 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ & ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −26→26
Tmin = 0.915, Tmax = 0.935	k = −19→18
35350 measured reflections	l = −18→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0508P)2 + 1.7012P] where P = (Fo2 + 2Fc2)/3
9412 reflections	(Δ/σ)max = 0.001
555 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.46 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	0.5000	0.5000	0.5000	0.01691 (10)
O1	0.61077 (8)	0.68067 (10)	1.22601 (11)	0.0260 (4)
H1WA	0.5871	0.6602	1.2604	0.039*
H1WB	0.5975	0.7337	1.2064	0.039*
N1	0.53010 (10)	0.62058 (14)	0.34081 (15)	0.0311 (5)
C1	0.51810 (11)	0.57457 (15)	0.39874 (16)	0.0213 (5)
Fe2	1.0000	0.5000	0.5000	0.01750 (11)
O2	0.74379 (8)	0.17371 (11)	−0.01841 (13)	0.0350 (4)
H2WA	0.7173	0.1443	0.0054	0.053*
H2WB	0.7779	0.1410	−0.0175	0.053*
N2	0.56126 (11)	0.65586 (14)	0.64662 (15)	0.0339 (5)
C2	0.53866 (12)	0.59643 (15)	0.59344 (16)	0.0236 (5)
O3	0.90143 (8)	0.68762 (10)	0.10957 (12)	0.0296 (4)
H3WA	0.9130	0.6578	0.1638	0.044*
H3WB	0.9316	0.7276	0.1129	0.044*
N3	0.64249 (10)	0.40996 (14)	0.54417 (15)	0.0320 (5)
C3	0.59010 (11)	0.44465 (15)	0.52866 (16)	0.0226 (5)
O4	0.74538 (11)	0.80279 (16)	−0.1391 (2)	0.0725 (8)
H4	0.7081	0.8116	−0.1855	0.087*
N4	0.86099 (10)	0.42701 (15)	0.50654 (15)	0.0344 (5)
C4	0.91260 (11)	0.45459 (15)	0.50366 (16)	0.0226 (5)
N5	0.92963 (11)	0.60560 (14)	0.30400 (15)	0.0337 (5)
C5	0.95502 (11)	0.56681 (16)	0.37726 (17)	0.0237 (5)
N6	0.98584 (11)	0.66414 (14)	0.62580 (15)	0.0316 (5)
C6	0.99123 (11)	0.60252 (15)	0.57895 (16)	0.0220 (5)
N7	0.58878 (9)	0.59499 (12)	1.05172 (13)	0.0208 (4)
H7A	0.5982	0.6111	1.1146	0.025*
C7	0.57651 (11)	0.65885 (16)	0.98177 (17)	0.0248 (5)
H7	0.5778	0.7203	1.0006	0.030*
N8	0.61145 (10)	0.47211 (13)	1.20218 (14)	0.0250 (4)
C8	0.56189 (11)	0.63637 (16)	0.88212 (17)	0.0273 (5)
H8	0.5537	0.6821	0.8328	0.033*
N9	0.89140 (9)	0.61601 (13)	−0.06545 (14)	0.0240 (4)
H9A	0.8970	0.6263	−0.0021	0.029*
C9	0.55926 (11)	0.54730 (17)	0.85518 (17)	0.0256 (5)
H9	0.5487	0.5314	0.7868	0.031*
N10	0.92307 (9)	0.48236 (13)	0.07413 (14)	0.0237 (4)
C10	0.57223 (10)	0.47915 (15)	0.92884 (16)	0.0211 (5)
N11	0.73512 (9)	0.38648 (14)	−0.10638 (15)	0.0286 (4)
C11	0.57002 (11)	0.38495 (16)	0.90624 (17)	0.0249 (5)
H11	0.5600	0.3659	0.8389	0.030*
N12	0.76927 (9)	0.32388 (14)	0.08598 (15)	0.0284 (5)
H12A	0.7607	0.2874	0.0344	0.034*
C12	0.58206 (11)	0.32297 (16)	0.98008 (17)	0.0261 (5)
H12	0.5806	0.2609	0.9637	0.031*
C13	0.59700 (10)	0.34912 (15)	1.08258 (16)	0.0221 (5)
C14	0.60826 (11)	0.28672 (16)	1.16144 (17)	0.0277 (5)
H14	0.6071	0.2239	1.1486	0.033*
C15	0.62086 (12)	0.31807 (16)	1.25668 (18)	0.0315 (6)
H15	0.6290	0.2772	1.3109	0.038*
C16	0.62168 (12)	0.41098 (16)	1.27358 (17)	0.0300 (5)
H16	0.6301	0.4313	1.3401	0.036*
C17	0.59953 (10)	0.44070 (15)	1.10768 (16)	0.0199 (5)
C18	0.58720 (10)	0.50614 (15)	1.02921 (15)	0.0194 (4)
C19	0.87499 (12)	0.68438 (17)	−0.12971 (19)	0.0311 (6)
H19	0.8695	0.7429	−0.1065	0.037*
C20	0.86585 (12)	0.67089 (18)	−0.23002 (19)	0.0345 (6)
H20	0.8537	0.7197	−0.2757	0.041*
C21	0.87446 (11)	0.58643 (18)	−0.26289 (18)	0.0318 (6)
H21	0.8687	0.5768	−0.3315	0.038*
C22	0.89188 (11)	0.51358 (16)	−0.19514 (17)	0.0260 (5)
C23	0.90248 (12)	0.42396 (18)	−0.22367 (18)	0.0320 (6)
H23	0.8981	0.4116	−0.2913	0.038*
C24	0.91866 (12)	0.35646 (17)	−0.15582 (18)	0.0308 (6)
H24	0.9256	0.2976	−0.1766	0.037*
C25	0.92544 (11)	0.37243 (15)	−0.05304 (16)	0.0235 (5)
C26	0.94197 (12)	0.30442 (16)	0.02035 (18)	0.0294 (5)
H26	0.9479	0.2440	0.0030	0.035*
C27	0.94935 (12)	0.32691 (16)	0.11723 (18)	0.0286 (5)
H27	0.9610	0.2821	0.1679	0.034*
C28	0.93975 (11)	0.41590 (16)	0.14109 (17)	0.0268 (5)
H28	0.9454	0.4299	0.2088	0.032*
C29	0.91672 (10)	0.46000 (15)	−0.02137 (16)	0.0201 (5)
C30	0.89972 (10)	0.53096 (15)	−0.09443 (16)	0.0214 (5)
C31	0.71790 (12)	0.41970 (18)	−0.19830 (18)	0.0332 (6)
H31	0.7101	0.3785	−0.2521	0.040*
C32	0.71043 (12)	0.51142 (19)	−0.2212 (2)	0.0372 (6)
H32	0.6975	0.5311	−0.2887	0.045*
C33	0.72208 (12)	0.57241 (18)	−0.1450 (2)	0.0362 (6)
H33	0.7178	0.6351	−0.1587	0.043*
C34	0.74048 (11)	0.54076 (17)	−0.04558 (19)	0.0298 (6)
C35	0.75300 (12)	0.59971 (19)	0.0385 (2)	0.0403 (7)
H35	0.7491	0.6628	0.0278	0.048*
C36	0.77032 (12)	0.5672 (2)	0.1328 (2)	0.0410 (7)
H36	0.7782	0.6077	0.1873	0.049*
C37	0.77683 (12)	0.47259 (18)	0.15146 (19)	0.0332 (6)
C38	0.79561 (13)	0.4349 (2)	0.2477 (2)	0.0451 (7)
H38	0.8049	0.4732	0.3043	0.054*
C39	0.80072 (14)	0.3435 (2)	0.2609 (2)	0.0482 (8)
H39	0.8135	0.3183	0.3261	0.058*
C40	0.78688 (13)	0.2887 (2)	0.17787 (19)	0.0398 (6)
H40	0.7899	0.2253	0.1861	0.048*
C41	0.76419 (10)	0.41360 (17)	0.06965 (18)	0.0268 (5)
C42	0.74609 (10)	0.44752 (16)	−0.03118 (17)	0.0254 (5)
C43	0.7239 (2)	0.8784 (3)	0.0029 (3)	0.0806 (12)
H43A	0.6742	0.8733	−0.0309	0.121*
H43B	0.7340	0.9349	0.0406	0.121*
H43C	0.7399	0.8277	0.0489	0.121*
C44	0.7595 (2)	0.8775 (3)	−0.0716 (3)	0.0795 (12)
H44A	0.7473	0.9333	−0.1116	0.095*
H44B	0.8096	0.8792	−0.0357	0.095*

	U11	U22	U33	U12	U13	U23
Fe1	0.0227 (2)	0.0143 (2)	0.0139 (2)	−0.00103 (17)	0.00619 (16)	−0.00050 (18)
O1	0.0348 (9)	0.0182 (8)	0.0268 (9)	0.0025 (7)	0.0125 (7)	0.0052 (7)
N1	0.0398 (11)	0.0297 (12)	0.0240 (11)	−0.0038 (9)	0.0110 (9)	0.0042 (9)
C1	0.0251 (11)	0.0205 (12)	0.0170 (11)	−0.0003 (9)	0.0052 (9)	−0.0022 (9)
Fe2	0.0213 (2)	0.0155 (2)	0.0160 (2)	0.00027 (17)	0.00647 (16)	0.00038 (18)
O2	0.0283 (9)	0.0290 (10)	0.0509 (11)	0.0027 (7)	0.0172 (8)	0.0052 (8)
N2	0.0521 (13)	0.0237 (12)	0.0236 (11)	−0.0071 (10)	0.0093 (9)	−0.0031 (9)
C2	0.0334 (12)	0.0205 (12)	0.0170 (11)	0.0002 (9)	0.0084 (9)	0.0042 (9)
O3	0.0388 (9)	0.0227 (9)	0.0267 (9)	−0.0063 (7)	0.0099 (7)	0.0001 (7)
N3	0.0315 (11)	0.0302 (12)	0.0354 (12)	0.0027 (9)	0.0125 (9)	0.0045 (9)
C3	0.0292 (12)	0.0207 (12)	0.0183 (11)	−0.0015 (9)	0.0084 (9)	0.0017 (9)
O4	0.0425 (13)	0.0613 (16)	0.0932 (19)	0.0131 (11)	−0.0054 (12)	−0.0321 (14)
N4	0.0324 (11)	0.0392 (13)	0.0321 (12)	−0.0054 (9)	0.0113 (9)	−0.0005 (10)
C4	0.0268 (11)	0.0223 (12)	0.0171 (11)	−0.0007 (9)	0.0052 (9)	−0.0011 (9)
N5	0.0418 (12)	0.0306 (12)	0.0253 (11)	0.0016 (9)	0.0063 (9)	0.0041 (9)
C5	0.0270 (11)	0.0221 (12)	0.0226 (12)	−0.0007 (9)	0.0088 (9)	−0.0007 (10)
N6	0.0442 (12)	0.0250 (12)	0.0277 (11)	0.0042 (9)	0.0148 (9)	−0.0003 (9)
C6	0.0253 (11)	0.0226 (12)	0.0180 (11)	0.0003 (9)	0.0071 (9)	0.0048 (9)
N7	0.0221 (9)	0.0219 (10)	0.0185 (9)	0.0013 (7)	0.0070 (7)	0.0020 (8)
C7	0.0255 (11)	0.0233 (12)	0.0273 (13)	0.0011 (9)	0.0109 (9)	0.0053 (10)
N8	0.0312 (10)	0.0250 (11)	0.0190 (10)	0.0011 (8)	0.0085 (8)	0.0020 (8)
C8	0.0294 (12)	0.0298 (14)	0.0250 (12)	0.0041 (10)	0.0120 (10)	0.0087 (10)
N9	0.0238 (9)	0.0255 (11)	0.0223 (10)	−0.0011 (8)	0.0068 (8)	0.0024 (8)
C9	0.0209 (11)	0.0386 (15)	0.0179 (12)	0.0009 (10)	0.0073 (9)	0.0044 (10)
N10	0.0224 (9)	0.0290 (12)	0.0196 (10)	−0.0015 (8)	0.0067 (7)	0.0001 (8)
C10	0.0173 (10)	0.0280 (13)	0.0188 (11)	0.0015 (8)	0.0070 (8)	0.0009 (9)
N11	0.0264 (10)	0.0310 (12)	0.0275 (11)	−0.0008 (8)	0.0076 (8)	0.0004 (9)
C11	0.0229 (11)	0.0304 (13)	0.0213 (12)	−0.0011 (9)	0.0072 (9)	−0.0047 (10)
N12	0.0257 (10)	0.0335 (12)	0.0246 (11)	0.0004 (8)	0.0063 (8)	0.0007 (9)
C12	0.0261 (11)	0.0231 (13)	0.0284 (13)	0.0004 (9)	0.0080 (10)	−0.0031 (10)
C13	0.0206 (10)	0.0217 (12)	0.0233 (12)	0.0006 (9)	0.0062 (9)	−0.0011 (10)
C14	0.0314 (12)	0.0219 (13)	0.0280 (13)	0.0017 (10)	0.0072 (10)	0.0027 (10)
C15	0.0403 (14)	0.0250 (14)	0.0288 (13)	0.0012 (10)	0.0108 (11)	0.0079 (11)
C16	0.0377 (13)	0.0316 (14)	0.0199 (12)	0.0012 (11)	0.0084 (10)	0.0029 (10)
C17	0.0182 (10)	0.0212 (12)	0.0194 (11)	0.0001 (8)	0.0048 (8)	−0.0003 (9)
C18	0.0167 (9)	0.0227 (12)	0.0198 (11)	0.0007 (9)	0.0073 (8)	0.0007 (10)
C19	0.0285 (12)	0.0263 (13)	0.0390 (15)	0.0001 (10)	0.0117 (11)	0.0077 (11)
C20	0.0314 (13)	0.0377 (16)	0.0336 (14)	0.0014 (11)	0.0094 (11)	0.0154 (12)
C21	0.0251 (12)	0.0462 (17)	0.0247 (13)	−0.0008 (11)	0.0092 (10)	0.0080 (12)
C22	0.0196 (10)	0.0371 (15)	0.0203 (11)	−0.0004 (9)	0.0052 (9)	0.0023 (10)
C23	0.0325 (13)	0.0422 (16)	0.0221 (13)	0.0014 (11)	0.0100 (10)	−0.0050 (11)
C24	0.0336 (13)	0.0297 (14)	0.0304 (14)	0.0030 (10)	0.0123 (11)	−0.0064 (11)
C25	0.0213 (11)	0.0251 (13)	0.0231 (12)	−0.0005 (9)	0.0059 (9)	−0.0007 (10)
C26	0.0296 (12)	0.0238 (13)	0.0347 (14)	0.0021 (10)	0.0105 (10)	−0.0008 (11)
C27	0.0310 (12)	0.0258 (13)	0.0289 (13)	0.0016 (10)	0.0095 (10)	0.0091 (11)
C28	0.0263 (11)	0.0329 (14)	0.0198 (12)	−0.0002 (10)	0.0059 (9)	0.0037 (10)
C29	0.0150 (9)	0.0252 (12)	0.0189 (11)	−0.0009 (8)	0.0040 (8)	0.0008 (9)
C30	0.0175 (10)	0.0228 (12)	0.0234 (12)	−0.0002 (8)	0.0060 (9)	0.0012 (9)
C31	0.0284 (12)	0.0415 (16)	0.0278 (14)	−0.0030 (11)	0.0067 (10)	0.0015 (12)
C32	0.0268 (12)	0.0450 (18)	0.0389 (15)	−0.0004 (11)	0.0094 (11)	0.0148 (13)
C33	0.0239 (12)	0.0306 (15)	0.0531 (17)	−0.0003 (10)	0.0110 (11)	0.0106 (13)
C34	0.0178 (11)	0.0293 (14)	0.0404 (15)	−0.0033 (9)	0.0070 (10)	−0.0004 (12)
C35	0.0251 (12)	0.0316 (15)	0.0607 (19)	−0.0029 (10)	0.0095 (13)	−0.0089 (14)
C36	0.0246 (12)	0.0455 (17)	0.0493 (18)	−0.0052 (11)	0.0074 (12)	−0.0209 (14)
C37	0.0209 (11)	0.0451 (16)	0.0320 (14)	−0.0035 (10)	0.0064 (10)	−0.0099 (12)
C38	0.0339 (14)	0.070 (2)	0.0295 (15)	−0.0006 (14)	0.0082 (11)	−0.0141 (15)
C39	0.0469 (16)	0.070 (2)	0.0255 (15)	0.0043 (15)	0.0094 (12)	0.0062 (15)
C40	0.0349 (14)	0.0510 (18)	0.0328 (15)	0.0052 (12)	0.0103 (11)	0.0091 (13)
C41	0.0159 (10)	0.0329 (14)	0.0303 (13)	−0.0012 (9)	0.0059 (9)	−0.0037 (11)
C42	0.0151 (10)	0.0305 (14)	0.0295 (13)	−0.0009 (9)	0.0056 (9)	0.0009 (10)
C43	0.069 (2)	0.093 (3)	0.067 (3)	0.024 (2)	0.005 (2)	−0.012 (2)
C44	0.070 (2)	0.063 (3)	0.107 (3)	−0.024 (2)	0.031 (2)	−0.037 (2)

Fe1—C2	1.937 (2)	C13—C14	1.412 (3)
Fe1—C2i	1.937 (2)	C14—C15	1.369 (3)
Fe1—C1i	1.943 (2)	C14—H14	0.9500
Fe1—C1	1.943 (2)	C15—C16	1.402 (3)
Fe1—C3	1.946 (2)	C15—H15	0.9500
Fe1—C3i	1.946 (2)	C16—H16	0.9500
O1—H1WA	0.8500	C17—C18	1.436 (3)
O1—H1WB	0.8501	C19—C20	1.385 (4)
N1—C1	1.155 (3)	C19—H19	0.9500
Fe2—C6	1.934 (2)	C20—C21	1.371 (4)
Fe2—C6ii	1.934 (2)	C20—H20	0.9500
Fe2—C4ii	1.937 (2)	C21—C22	1.413 (3)
Fe2—C4	1.937 (2)	C21—H21	0.9500
Fe2—C5ii	1.952 (2)	C22—C30	1.406 (3)
Fe2—C5	1.952 (2)	C22—C23	1.430 (3)
O2—H2WA	0.8499	C23—C24	1.354 (3)
O2—H2WB	0.8503	C23—H23	0.9500
N2—C2	1.156 (3)	C24—C25	1.436 (3)
O3—H3WA	0.8502	C24—H24	0.9500
O3—H3WB	0.8503	C25—C29	1.408 (3)
N3—C3	1.149 (3)	C25—C26	1.410 (3)
O4—C44	1.432 (4)	C26—C27	1.371 (3)
O4—H4	0.8400	C26—H26	0.9500
N4—C4	1.151 (3)	C27—C28	1.396 (3)
N5—C5	1.152 (3)	C27—H27	0.9500
N6—C6	1.158 (3)	C28—H28	0.9500
N7—C7	1.335 (3)	C29—C30	1.439 (3)
N7—C18	1.357 (3)	C31—C32	1.399 (4)
N7—H7A	0.8800	C31—H31	0.9500
C7—C8	1.384 (3)	C32—C33	1.370 (4)
C7—H7	0.9500	C32—H32	0.9500
N8—C16	1.324 (3)	C33—C34	1.413 (4)
N8—C17	1.362 (3)	C33—H33	0.9500
C8—C9	1.375 (3)	C34—C42	1.401 (3)
C8—H8	0.9500	C34—C35	1.432 (4)
N9—C19	1.332 (3)	C35—C36	1.354 (4)
N9—C30	1.358 (3)	C35—H35	0.9500
N9—H9A	0.8800	C36—C37	1.429 (4)
C9—C10	1.416 (3)	C36—H36	0.9500
C9—H9	0.9500	C37—C38	1.406 (4)
N10—C28	1.334 (3)	C37—C41	1.408 (3)
N10—C29	1.357 (3)	C38—C39	1.372 (4)
C10—C18	1.410 (3)	C38—H38	0.9500
C10—C11	1.435 (3)	C39—C40	1.381 (4)
N11—C31	1.327 (3)	C39—H39	0.9500
N11—C42	1.361 (3)	C40—H40	0.9500
C11—C12	1.354 (3)	C41—C42	1.443 (3)
C11—H11	0.9500	C43—C44	1.468 (5)
N12—C40	1.337 (3)	C43—H43A	0.9800
N12—C41	1.352 (3)	C43—H43B	0.9800
N12—H12A	0.8800	C43—H43C	0.9800
C12—C13	1.435 (3)	C44—H44A	0.9900
C12—H12	0.9500	C44—H44B	0.9900
C13—C17	1.404 (3)
C2—Fe1—C2i	180.0	N7—C18—C17	119.59 (19)
C2—Fe1—C1i	93.08 (9)	C10—C18—C17	120.8 (2)
C2i—Fe1—C1i	86.92 (9)	N9—C19—C20	120.6 (2)
C2—Fe1—C1	86.92 (9)	N9—C19—H19	119.7
C2i—Fe1—C1	93.08 (9)	C20—C19—H19	119.7
C1i—Fe1—C1	180.0	C21—C20—C19	119.4 (2)
C2—Fe1—C3	91.20 (9)	C21—C20—H20	120.3
C2i—Fe1—C3	88.80 (9)	C19—C20—H20	120.3
C1i—Fe1—C3	90.25 (9)	C20—C21—C22	120.3 (2)
C1—Fe1—C3	89.75 (9)	C20—C21—H21	119.9
C2—Fe1—C3i	88.80 (9)	C22—C21—H21	119.9
C2i—Fe1—C3i	91.20 (9)	C30—C22—C21	117.8 (2)
C1i—Fe1—C3i	89.75 (9)	C30—C22—C23	118.7 (2)
C1—Fe1—C3i	90.25 (9)	C21—C22—C23	123.4 (2)
C3—Fe1—C3i	180.0	C24—C23—C22	121.0 (2)
H1WA—O1—H1WB	109.7	C24—C23—H23	119.5
N1—C1—Fe1	177.9 (2)	C22—C23—H23	119.5
C6—Fe2—C6ii	180.0	C23—C24—C25	121.1 (2)
C6—Fe2—C4ii	90.21 (9)	C23—C24—H24	119.5
C6ii—Fe2—C4ii	89.79 (9)	C25—C24—H24	119.5
C6—Fe2—C4	89.79 (9)	C29—C25—C26	117.0 (2)
C6ii—Fe2—C4	90.21 (9)	C29—C25—C24	119.7 (2)
C4ii—Fe2—C4	180.0	C26—C25—C24	123.3 (2)
C6—Fe2—C5ii	89.63 (9)	C27—C26—C25	118.9 (2)
C6ii—Fe2—C5ii	90.37 (9)	C27—C26—H26	120.5
C4ii—Fe2—C5ii	91.60 (9)	C25—C26—H26	120.5
C4—Fe2—C5ii	88.40 (9)	C26—C27—C28	119.7 (2)
C6—Fe2—C5	90.37 (9)	C26—C27—H27	120.2
C6ii—Fe2—C5	89.63 (9)	C28—C27—H27	120.2
C4ii—Fe2—C5	88.40 (9)	N10—C28—C27	123.7 (2)
C4—Fe2—C5	91.60 (9)	N10—C28—H28	118.2
C5ii—Fe2—C5	180.0	C27—C28—H28	118.2
H2WA—O2—H2WB	109.4	N10—C29—C25	124.3 (2)
N2—C2—Fe1	177.8 (2)	N10—C29—C30	117.3 (2)
H3WA—O3—H3WB	109.4	C25—C29—C30	118.4 (2)
N3—C3—Fe1	178.2 (2)	N9—C30—C22	119.6 (2)
C44—O4—H4	109.5	N9—C30—C29	119.4 (2)
N4—C4—Fe2	179.3 (2)	C22—C30—C29	121.0 (2)
N5—C5—Fe2	178.5 (2)	N11—C31—C32	124.4 (2)
N6—C6—Fe2	179.7 (2)	N11—C31—H31	117.8
C7—N7—C18	122.30 (19)	C32—C31—H31	117.8
C7—N7—H7A	118.9	C33—C32—C31	119.0 (2)
C18—N7—H7A	118.9	C33—C32—H32	120.5
N7—C7—C8	120.6 (2)	C31—C32—H32	120.5
N7—C7—H7	119.7	C32—C33—C34	119.0 (2)
C8—C7—H7	119.7	C32—C33—H33	120.5
C16—N8—C17	116.6 (2)	C34—C33—H33	120.5
C9—C8—C7	119.4 (2)	C42—C34—C33	117.2 (2)
C9—C8—H8	120.3	C42—C34—C35	120.1 (2)
C7—C8—H8	120.3	C33—C34—C35	122.7 (3)
C19—N9—C30	122.2 (2)	C36—C35—C34	121.2 (3)
C19—N9—H9A	118.9	C36—C35—H35	119.4
C30—N9—H9A	118.9	C34—C35—H35	119.4
C8—C9—C10	120.3 (2)	C35—C36—C37	120.8 (3)
C8—C9—H9	119.8	C35—C36—H36	119.6
C10—C9—H9	119.8	C37—C36—H36	119.6
C28—N10—C29	116.4 (2)	C38—C37—C41	117.8 (3)
C18—C10—C9	117.7 (2)	C38—C37—C36	123.5 (3)
C18—C10—C11	118.9 (2)	C41—C37—C36	118.7 (2)
C9—C10—C11	123.4 (2)	C39—C38—C37	120.8 (3)
C31—N11—C42	116.2 (2)	C39—C38—H38	119.6
C12—C11—C10	120.5 (2)	C37—C38—H38	119.6
C12—C11—H11	119.7	C38—C39—C40	118.9 (3)
C10—C11—H11	119.7	C38—C39—H39	120.6
C40—N12—C41	122.2 (2)	C40—C39—H39	120.6
C40—N12—H12A	118.9	N12—C40—C39	120.8 (3)
C41—N12—H12A	118.9	N12—C40—H40	119.6
C11—C12—C13	121.4 (2)	C39—C40—H40	119.6
C11—C12—H12	119.3	N12—C41—C37	119.4 (2)
C13—C12—H12	119.3	N12—C41—C42	119.6 (2)
C17—C13—C14	117.0 (2)	C37—C41—C42	120.9 (2)
C17—C13—C12	119.8 (2)	N11—C42—C34	124.2 (2)
C14—C13—C12	123.2 (2)	N11—C42—C41	117.6 (2)
C15—C14—C13	119.0 (2)	C34—C42—C41	118.2 (2)
C15—C14—H14	120.5	C44—C43—H43A	109.5
C13—C14—H14	120.5	C44—C43—H43B	109.5
C14—C15—C16	119.5 (2)	H43A—C43—H43B	109.5
C14—C15—H15	120.3	C44—C43—H43C	109.5
C16—C15—H15	120.3	H43A—C43—H43C	109.5
N8—C16—C15	123.8 (2)	H43B—C43—H43C	109.5
N8—C16—H16	118.1	O4—C44—C43	116.6 (3)
C15—C16—H16	118.1	O4—C44—H44A	108.1
N8—C17—C13	124.1 (2)	C43—C44—H44A	108.1
N8—C17—C18	117.20 (19)	O4—C44—H44B	108.1
C13—C17—C18	118.6 (2)	C43—C44—H44B	108.1
N7—C18—C10	119.62 (19)	H44A—C44—H44B	107.3

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1WA···N1iii	0.85	1.97	2.822 (2)	176
O1—H1WB···N2iv	0.85	1.89	2.732 (3)	172
O2—H2WA···N3v	0.85	1.97	2.809 (3)	169
O2—H2WB···N4v	0.85	1.92	2.761 (3)	171
O3—H3WA···N5	0.85	2.05	2.891 (3)	168
O3—H3WB···N6vi	0.85	1.93	2.769 (3)	168
N7—H7A···O1	0.88	1.83	2.681 (2)	161
N9—H9A···O3	0.88	1.80	2.643 (2)	159
N12—H12A···O2	0.88	1.84	2.635 (3)	150
O4—H4···O1vii	0.84	1.99	2.813 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1WA⋯N1i	0.85	1.97	2.822 (2)	176
O1—H1WB⋯N2ii	0.85	1.89	2.732 (3)	172
O2—H2WA⋯N3iii	0.85	1.97	2.809 (3)	169
O2—H2WB⋯N4iii	0.85	1.92	2.761 (3)	171
O3—H3WA⋯N5	0.85	2.05	2.891 (3)	168
O3—H3WB⋯N6iv	0.85	1.93	2.769 (3)	168
N7—H7A⋯O1	0.88	1.83	2.681 (2)	161
N9—H9A⋯O3	0.88	1.80	2.643 (2)	159
N12—H12A⋯O2	0.88	1.84	2.635 (3)	150
O4—H4⋯O1v	0.84	1.99	2.813 (3)	167

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