2,6-Diamino-pyridinium bis-(4-hydroxy-pyridine-2,6-dicarboxyl-ato-κO,N,O)ferrate(III) dihydrate.

The reaction of iron(II) sulfate hepta-hydrate with the proton-transfer compound (pydaH)(hypydcH) (pyda = pyridine-2,6-diamine; hypydcH(2) = 4-hydroxy-pyridine-2,6-dicarboxylic acid) in an aqueous solution led to the formation of the title compound, (C(5)H(8)N(3))[Fe(C(7)H(3)NO(5))(2)]·2H(2)O. The anion is a six-coordinated complex with a distorted octa-hedral geometry around the Fe(III) atom. Extensive inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, involving the complex anion, (pydaH)(+) counter-ion and two uncoordinated water mol-ecules, and π-π [centroid-to-centroid distance 3.323 (11) Å] and C-O⋯π [O-centroid distance 3.150 (15) Å] inter-actions connect the various components into a supra-molecular structure.

Related literature

For other complexes with pyridine­dicarboxylic acids, see: Rafizadeh et al. (2004 ▶, 2006 ▶, 2007a ▶,b ▶); Rafizadeh & Amani (2006 ▶).

Experimental

Crystal data

(C5H8N3)[Fe(C7H3NO5)2]·2H2O

M = 564.23

Monoclinic,

a = 6.9389 (4) Å

b = 20.8845 (12) Å

c = 14.9908 (8) Å

β = 96.371 (1)°

V = 2159.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.78 mm−1

T = 100 (2) K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.746, T max = 0.860

33555 measured reflections

8157 independent reflections

5648 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.110

S = 1.02

8157 reflections

342 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.61 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808029280/hy2152sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029280/hy2152Isup2.hkl

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

(C5H8N3)[Fe(C7H3NO5)2]·2H2O	F(000) = 1156
Mr = 564.23	Dx = 1.736 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4719 reflections
a = 6.9389 (4) Å	θ = 2.4–31.9°
b = 20.8845 (12) Å	µ = 0.78 mm−1
c = 14.9908 (8) Å	T = 100 K
β = 96.371 (1)°	Prism, colourless
V = 2159.0 (2) Å3	0.40 × 0.40 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	8157 independent reflections
Radiation source: fine-focus sealed tube	5648 reflections with I > 2σ(I)
graphite	Rint = 0.073
φ and ω scans	θmax = 33.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.746, Tmax = 0.860	k = −31→32
33555 measured reflections	l = −22→22

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)] = 0.045	Hydrogen site location: mixed
wR(F2) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.6357P] where P = (Fo2 + 2Fc2)/3
8157 reflections	(Δ/σ)max = 0.001
342 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.61 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.

	x	y	z	Uiso*/Ueq
Fe1	0.03345 (4)	0.098201 (12)	0.291874 (16)	0.01147 (7)
O1	0.18095 (19)	0.01628 (6)	0.33338 (8)	0.0138 (3)
O2	0.31460 (19)	−0.04217 (6)	0.44867 (9)	0.0154 (3)
O3	−0.08559 (19)	0.18304 (6)	0.31759 (8)	0.0147 (3)
O4	−0.1601 (2)	0.25261 (6)	0.42183 (9)	0.0164 (3)
O5	0.1267 (2)	0.11113 (7)	0.70162 (8)	0.0179 (3)
H5	0.0929	0.1486	0.7156	0.041 (8)*
N1	0.0599 (2)	0.10213 (7)	0.42918 (9)	0.0104 (3)
C1	0.2245 (3)	0.00489 (8)	0.41778 (12)	0.0119 (3)
C2	0.1537 (3)	0.05567 (8)	0.47787 (11)	0.0105 (3)
C3	0.1796 (3)	0.05772 (8)	0.56992 (11)	0.0120 (3)
H3A	0.2470	0.0246	0.6037	0.014*
C4	0.1027 (3)	0.11076 (8)	0.61299 (12)	0.0120 (3)
C5	0.0084 (3)	0.15997 (8)	0.56065 (12)	0.0119 (3)
H5A	−0.0422	0.1965	0.5879	0.014*
C6	−0.0080 (3)	0.15336 (8)	0.46877 (11)	0.0110 (3)
C7	−0.0940 (3)	0.20139 (9)	0.39982 (12)	0.0128 (3)
O6	0.28312 (19)	0.14151 (6)	0.26334 (8)	0.0149 (3)
O7	0.4605 (2)	0.17585 (7)	0.15648 (9)	0.0187 (3)
O8	−0.2194 (2)	0.05293 (6)	0.25578 (8)	0.0158 (3)
O9	−0.4188 (2)	0.01213 (7)	0.14115 (9)	0.0205 (3)
O10	−0.0042 (2)	0.09000 (7)	−0.11598 (9)	0.0201 (3)
H10	−0.1192	0.0795	−0.1361	0.039 (8)*
N2	0.0277 (2)	0.09017 (7)	0.15604 (10)	0.0117 (3)
C8	0.3215 (3)	0.14715 (9)	0.18084 (12)	0.0133 (3)
C9	0.1707 (3)	0.11574 (8)	0.11447 (12)	0.0120 (3)
C10	0.1645 (3)	0.11537 (9)	0.02270 (12)	0.0142 (3)
H10A	0.2677	0.1328	−0.0063	0.017*
C11	0.0007 (3)	0.08840 (9)	−0.02725 (12)	0.0146 (4)
C12	−0.1484 (3)	0.06195 (9)	0.01761 (12)	0.0140 (3)
H12A	−0.2596	0.0432	−0.0148	0.017*
C13	−0.1279 (3)	0.06408 (9)	0.11011 (12)	0.0129 (3)
C14	−0.2708 (3)	0.04000 (9)	0.17213 (12)	0.0144 (3)
N3	0.0302 (2)	0.33319 (7)	0.07019 (10)	0.0133 (3)
H3N	0.0921	0.3714	0.0844	0.028 (7)*
N4	0.0433 (3)	0.30671 (8)	0.22110 (11)	0.0195 (3)
H4NA	0.0914	0.3465	0.2380	0.045 (8)*
H4NB	−0.0055	0.2836	0.2658	0.051 (9)*
N5	0.0395 (2)	0.36729 (8)	−0.07645 (10)	0.0154 (3)
H5NA	0.0937	0.4051	−0.0543	0.029 (7)*
H5NB	−0.0126	0.3660	−0.1356	0.050 (9)*
C15	−0.0200 (3)	0.29254 (9)	0.13517 (12)	0.0140 (3)
C16	−0.1329 (3)	0.23951 (9)	0.10904 (13)	0.0160 (4)
H16A	−0.1734	0.2109	0.1526	0.019*
C17	−0.1855 (3)	0.22903 (9)	0.01850 (13)	0.0164 (4)
H17A	−0.2638	0.1929	0.0006	0.020*
C18	−0.1282 (3)	0.26914 (9)	−0.04682 (13)	0.0151 (4)
H18A	−0.1615	0.2601	−0.1087	0.018*
C19	−0.01989 (16)	0.32341 (5)	−0.01954 (7)	0.0129 (3)
O1W	0.05579 (16)	0.21932 (5)	0.77225 (7)	0.0176 (3)
H1WA	0.0359	0.2525	0.7396	0.042 (8)*
H1WB	0.1458	0.2209	0.8155	0.057 (10)*
O2W	−0.3280 (2)	0.06443 (7)	−0.21595 (9)	0.0173 (3)
H2WA	−0.2977	0.0393	−0.2567	0.045 (8)*
H2WB	−0.4203	0.0440	−0.1961	0.066 (11)*

	U11	U22	U33	U12	U13	U23
Fe1	0.01484 (13)	0.01232 (12)	0.00737 (11)	−0.00036 (10)	0.00172 (9)	0.00067 (9)
O1	0.0191 (7)	0.0131 (6)	0.0095 (6)	0.0017 (5)	0.0023 (5)	−0.0006 (5)
O2	0.0174 (7)	0.0130 (6)	0.0155 (6)	0.0031 (5)	0.0001 (5)	0.0004 (5)
O3	0.0197 (7)	0.0144 (6)	0.0101 (6)	0.0022 (5)	0.0022 (5)	0.0020 (5)
O4	0.0204 (7)	0.0131 (6)	0.0153 (6)	0.0033 (5)	0.0006 (5)	−0.0005 (5)
O5	0.0292 (8)	0.0171 (7)	0.0073 (6)	0.0023 (6)	0.0018 (5)	−0.0009 (5)
N1	0.0120 (7)	0.0103 (7)	0.0089 (6)	−0.0010 (5)	0.0013 (5)	−0.0004 (5)
C1	0.0124 (8)	0.0108 (8)	0.0129 (8)	−0.0026 (6)	0.0026 (6)	−0.0005 (6)
C2	0.0115 (8)	0.0097 (8)	0.0103 (8)	−0.0015 (6)	0.0016 (6)	0.0010 (6)
C3	0.0135 (8)	0.0110 (8)	0.0113 (8)	−0.0023 (6)	0.0010 (6)	0.0026 (6)
C4	0.0130 (8)	0.0130 (8)	0.0099 (7)	−0.0021 (6)	0.0006 (6)	−0.0007 (6)
C5	0.0137 (8)	0.0106 (8)	0.0119 (8)	−0.0021 (6)	0.0032 (6)	−0.0004 (6)
C6	0.0111 (8)	0.0113 (8)	0.0107 (8)	−0.0006 (6)	0.0016 (6)	0.0010 (6)
C7	0.0131 (8)	0.0130 (8)	0.0124 (8)	−0.0009 (7)	0.0023 (6)	0.0000 (6)
O6	0.0163 (7)	0.0183 (7)	0.0099 (6)	−0.0033 (5)	0.0011 (5)	0.0001 (5)
O7	0.0185 (7)	0.0222 (7)	0.0157 (6)	−0.0068 (6)	0.0034 (5)	0.0009 (5)
O8	0.0178 (7)	0.0201 (7)	0.0099 (6)	−0.0022 (5)	0.0024 (5)	0.0018 (5)
O9	0.0177 (7)	0.0250 (8)	0.0184 (7)	−0.0080 (6)	0.0001 (5)	0.0000 (6)
O10	0.0235 (8)	0.0282 (8)	0.0083 (6)	−0.0037 (6)	0.0009 (5)	−0.0014 (5)
N2	0.0138 (7)	0.0113 (7)	0.0101 (7)	−0.0003 (6)	0.0013 (5)	0.0008 (5)
C8	0.0163 (9)	0.0120 (8)	0.0114 (8)	−0.0002 (7)	0.0006 (6)	0.0005 (6)
C9	0.0140 (8)	0.0109 (8)	0.0116 (8)	−0.0003 (6)	0.0035 (6)	0.0005 (6)
C10	0.0181 (9)	0.0140 (8)	0.0110 (8)	−0.0009 (7)	0.0041 (7)	0.0008 (6)
C11	0.0208 (9)	0.0130 (8)	0.0102 (8)	0.0013 (7)	0.0024 (7)	−0.0011 (6)
C12	0.0172 (9)	0.0127 (8)	0.0117 (8)	−0.0010 (7)	−0.0011 (7)	−0.0008 (6)
C13	0.0158 (9)	0.0107 (8)	0.0124 (8)	−0.0005 (7)	0.0022 (7)	−0.0001 (6)
C14	0.0156 (9)	0.0138 (8)	0.0137 (8)	0.0003 (7)	0.0010 (7)	0.0020 (6)
N3	0.0132 (7)	0.0133 (7)	0.0132 (7)	0.0000 (6)	0.0012 (6)	0.0014 (6)
N4	0.0245 (9)	0.0203 (9)	0.0135 (8)	−0.0020 (7)	0.0012 (6)	0.0044 (6)
N5	0.0178 (8)	0.0167 (8)	0.0114 (7)	−0.0017 (6)	0.0010 (6)	−0.0002 (6)
C15	0.0133 (9)	0.0142 (8)	0.0147 (8)	0.0019 (7)	0.0025 (7)	0.0027 (7)
C16	0.0158 (9)	0.0126 (8)	0.0201 (9)	0.0023 (7)	0.0034 (7)	0.0036 (7)
C17	0.0144 (9)	0.0114 (8)	0.0234 (10)	0.0019 (7)	0.0020 (7)	−0.0021 (7)
C18	0.0153 (9)	0.0146 (9)	0.0155 (8)	0.0020 (7)	0.0023 (7)	−0.0023 (7)
C19	0.0108 (8)	0.0153 (8)	0.0128 (8)	0.0037 (7)	0.0021 (6)	−0.0002 (6)
O1W	0.0221 (7)	0.0167 (7)	0.0134 (6)	0.0014 (6)	−0.0011 (5)	−0.0008 (5)
O2W	0.0201 (7)	0.0194 (7)	0.0129 (6)	−0.0013 (6)	0.0041 (5)	−0.0039 (5)

Fe1—O3	2.0101 (13)	N2—C9	1.340 (2)
Fe1—O8	2.0135 (14)	C8—C9	1.511 (3)
Fe1—N2	2.0392 (15)	C9—C10	1.372 (2)
Fe1—O6	2.0413 (13)	C10—C11	1.407 (3)
Fe1—N1	2.0478 (14)	C10—H10A	0.9500
Fe1—O1	2.0544 (13)	C11—C12	1.408 (3)
O1—C1	1.290 (2)	C12—C13	1.379 (2)
O2—C1	1.227 (2)	C12—H12A	0.9500
O3—C7	1.298 (2)	C13—C14	1.518 (3)
O4—C7	1.224 (2)	N3—C15	1.366 (2)
O5—C4	1.321 (2)	N3—C19	1.3668 (18)
O5—H5	0.8501	N3—H3N	0.9200
N1—C6	1.335 (2)	N4—C15	1.347 (2)
N1—C2	1.339 (2)	N4—H4NA	0.9200
C1—C2	1.509 (2)	N4—H4NB	0.9200
C2—C3	1.372 (2)	N5—C19	1.3475 (19)
C3—C4	1.416 (2)	N5—H5NA	0.9200
C3—H3A	0.9500	N5—H5NB	0.9199
C4—C5	1.409 (2)	C15—C16	1.388 (3)
C5—C6	1.376 (2)	C16—C17	1.383 (3)
C5—H5A	0.9500	C16—H16A	0.9500
C6—C7	1.514 (2)	C17—C18	1.380 (3)
O6—C8	1.299 (2)	C17—H17A	0.9500
O7—C8	1.225 (2)	C18—C19	1.396 (2)
O8—C14	1.294 (2)	C18—H18A	0.9500
O9—C14	1.226 (2)	O1W—H1WA	0.8499
O10—C11	1.327 (2)	O1W—H1WB	0.8500
O10—H10	0.8500	O2W—H2WA	0.8500
N2—C13	1.331 (2)	O2W—H2WB	0.8499
O3—Fe1—O8	95.80 (6)	O7—C8—O6	125.40 (17)
O3—Fe1—N2	107.52 (6)	O7—C8—C9	121.77 (16)
O8—Fe1—N2	76.88 (6)	O6—C8—C9	112.80 (15)
O3—Fe1—O6	91.49 (5)	N2—C9—C10	121.45 (17)
O8—Fe1—O6	152.40 (5)	N2—C9—C8	111.18 (15)
N2—Fe1—O6	75.54 (6)	C10—C9—C8	127.24 (16)
O3—Fe1—N1	76.40 (5)	C9—C10—C11	117.99 (17)
O8—Fe1—N1	105.50 (6)	C9—C10—H10A	121.0
N2—Fe1—N1	175.34 (6)	C11—C10—H10A	121.0
O6—Fe1—N1	102.08 (5)	O10—C11—C10	116.88 (17)
O3—Fe1—O1	151.34 (5)	O10—C11—C12	123.40 (17)
O8—Fe1—O1	94.61 (5)	C10—C11—C12	119.72 (16)
N2—Fe1—O1	100.83 (5)	C13—C12—C11	117.96 (17)
O6—Fe1—O1	91.53 (5)	C13—C12—H12A	121.0
N1—Fe1—O1	75.10 (5)	C11—C12—H12A	121.0
C1—O1—Fe1	120.35 (11)	N2—C13—C12	121.36 (17)
C7—O3—Fe1	120.33 (11)	N2—C13—C14	111.48 (15)
C4—O5—H5	104.2	C12—C13—C14	127.15 (17)
C6—N1—C2	120.86 (15)	O9—C14—O8	126.56 (17)
C6—N1—Fe1	118.84 (12)	O9—C14—C13	120.12 (16)
C2—N1—Fe1	120.19 (12)	O8—C14—C13	113.32 (16)
O2—C1—O1	124.88 (16)	C15—N3—C19	123.48 (15)
O2—C1—C2	121.58 (16)	C15—N3—H3N	121.5
O1—C1—C2	113.54 (15)	C19—N3—H3N	114.8
N1—C2—C3	121.80 (16)	C15—N4—H4NA	122.1
N1—C2—C1	110.79 (14)	C15—N4—H4NB	118.2
C3—C2—C1	127.40 (16)	H4NA—N4—H4NB	115.2
C2—C3—C4	117.97 (16)	C19—N5—H5NA	119.7
C2—C3—H3A	121.0	C19—N5—H5NB	118.4
C4—C3—H3A	121.0	H5NA—N5—H5NB	118.3
O5—C4—C5	123.70 (16)	N4—C15—N3	117.61 (17)
O5—C4—C3	116.84 (16)	N4—C15—C16	124.00 (17)
C5—C4—C3	119.46 (16)	N3—C15—C16	118.39 (17)
C6—C5—C4	117.76 (16)	C17—C16—C15	118.84 (17)
C6—C5—H5A	121.1	C17—C16—H16A	120.6
C4—C5—H5A	121.1	C15—C16—H16A	120.6
N1—C6—C5	122.10 (16)	C18—C17—C16	122.33 (18)
N1—C6—C7	111.05 (14)	C18—C17—H17A	118.8
C5—C6—C7	126.81 (16)	C16—C17—H17A	118.8
O4—C7—O3	124.87 (17)	C17—C18—C19	118.23 (16)
O4—C7—C6	121.74 (16)	C17—C18—H18A	120.9
O3—C7—C6	113.38 (15)	C19—C18—H18A	120.9
C8—O6—Fe1	120.52 (12)	N5—C19—N3	117.33 (12)
C14—O8—Fe1	119.79 (12)	N5—C19—C18	124.01 (13)
C11—O10—H10	105.5	N3—C19—C18	118.66 (13)
C13—N2—C9	121.52 (15)	H1WA—O1W—H1WB	117.8
C13—N2—Fe1	118.37 (12)	H2WA—O2W—H2WB	101.4
C9—N2—Fe1	119.87 (12)
O3—Fe1—O1—C1	4.9 (2)	O3—Fe1—O8—C14	106.46 (14)
O8—Fe1—O1—C1	−106.13 (13)	N2—Fe1—O8—C14	−0.21 (13)
N2—Fe1—O1—C1	176.37 (13)	O6—Fe1—O8—C14	1.9 (2)
O6—Fe1—O1—C1	100.80 (13)	N1—Fe1—O8—C14	−176.08 (13)
N1—Fe1—O1—C1	−1.29 (13)	O1—Fe1—O8—C14	−100.28 (14)
O8—Fe1—O3—C7	104.38 (13)	O3—Fe1—N2—C13	−89.32 (14)
N2—Fe1—O3—C7	−177.58 (13)	O8—Fe1—N2—C13	2.70 (13)
O6—Fe1—O3—C7	−102.28 (13)	O6—Fe1—N2—C13	−176.26 (14)
N1—Fe1—O3—C7	−0.21 (13)	O1—Fe1—N2—C13	94.96 (14)
O1—Fe1—O3—C7	−6.4 (2)	O3—Fe1—N2—C9	85.10 (14)
O3—Fe1—N1—C6	0.52 (13)	O8—Fe1—N2—C9	177.12 (15)
O8—Fe1—N1—C6	−91.82 (14)	O6—Fe1—N2—C9	−1.85 (13)
O6—Fe1—N1—C6	89.12 (14)	O1—Fe1—N2—C9	−90.63 (14)
O1—Fe1—N1—C6	177.47 (14)	Fe1—O6—C8—O7	175.02 (15)
O3—Fe1—N1—C2	−175.72 (14)	Fe1—O6—C8—C9	−3.1 (2)
O8—Fe1—N1—C2	91.94 (14)	C13—N2—C9—C10	−0.9 (3)
O6—Fe1—N1—C2	−87.13 (14)	Fe1—N2—C9—C10	−175.18 (13)
O1—Fe1—N1—C2	1.22 (13)	C13—N2—C9—C8	175.08 (16)
Fe1—O1—C1—O2	−178.87 (14)	Fe1—N2—C9—C8	0.8 (2)
Fe1—O1—C1—C2	1.16 (19)	O7—C8—C9—N2	−176.81 (17)
C6—N1—C2—C3	1.7 (3)	O6—C8—C9—N2	1.4 (2)
Fe1—N1—C2—C3	177.91 (13)	O7—C8—C9—C10	−1.1 (3)
C6—N1—C2—C1	−177.17 (15)	O6—C8—C9—C10	177.16 (17)
Fe1—N1—C2—C1	−1.00 (19)	N2—C9—C10—C11	1.3 (3)
O2—C1—C2—N1	179.93 (16)	C8—C9—C10—C11	−174.01 (17)
O1—C1—C2—N1	−0.1 (2)	C9—C10—C11—C12	−1.1 (3)
O2—C1—C2—C3	1.1 (3)	O10—C11—C12—C13	−178.96 (17)
O1—C1—C2—C3	−178.93 (17)	C10—C11—C12—C13	0.5 (3)
N1—C2—C3—C4	0.3 (3)	C9—N2—C13—C12	0.3 (3)
C1—C2—C3—C4	179.06 (17)	Fe1—N2—C13—C12	174.63 (13)
C2—C3—C4—O5	178.92 (16)	C9—N2—C13—C14	−178.61 (16)
C2—C3—C4—C5	−1.8 (3)	Fe1—N2—C13—C14	−4.3 (2)
O5—C4—C5—C6	−179.53 (17)	C11—C12—C13—N2	−0.1 (3)
C3—C4—C5—C6	1.3 (3)	C11—C12—C13—C14	178.62 (17)
C2—N1—C6—C5	−2.4 (3)	Fe1—O8—C14—O9	179.03 (15)
Fe1—N1—C6—C5	−178.57 (13)	Fe1—O8—C14—C13	−1.9 (2)
C2—N1—C6—C7	175.52 (15)	N2—C13—C14—O9	−176.93 (17)
Fe1—N1—C6—C7	−0.69 (19)	C12—C13—C14—O9	4.2 (3)
C4—C5—C6—N1	0.8 (3)	N2—C13—C14—O8	3.9 (2)
C4—C5—C6—C7	−176.72 (17)	C12—C13—C14—O8	−174.90 (18)
Fe1—O3—C7—O4	178.48 (14)	C19—N3—C15—N4	178.12 (15)
Fe1—O3—C7—C6	−0.1 (2)	C19—N3—C15—C16	−2.1 (3)
N1—C6—C7—O4	−178.12 (17)	N4—C15—C16—C17	−178.46 (18)
C5—C6—C7—O4	−0.4 (3)	N3—C15—C16—C17	1.7 (3)
N1—C6—C7—O3	0.5 (2)	C15—C16—C17—C18	0.6 (3)
C5—C6—C7—O3	178.25 (17)	C16—C17—C18—C19	−2.6 (3)
O3—Fe1—O6—C8	−104.91 (13)	C15—N3—C19—N5	−179.87 (16)
O8—Fe1—O6—C8	0.6 (2)	C15—N3—C19—C18	0.0 (2)
N2—Fe1—O6—C8	2.80 (13)	C17—C18—C19—N5	−177.84 (16)
N1—Fe1—O6—C8	178.68 (13)	C17—C18—C19—N3	2.3 (2)
O1—Fe1—O6—C8	103.59 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2i	0.92	2.00	2.8431 (19)	152
N4—H4NA···O2Wii	0.92	2.04	2.957 (2)	173
N4—H4NB···O3	0.92	2.33	3.139 (2)	147
O5—H5···O1W	0.85	1.74	2.566 (2)	164
O10—H10···O2W	0.85	1.80	2.614 (2)	159
N5—H5NA···O2i	0.92	1.98	2.800 (2)	148
N5—H5NB···O6iii	0.92	1.96	2.832 (2)	157
O1W—H1WA···O7iv	0.85	1.98	2.826 (2)	173
O1W—H1WB···O4ii	0.85	2.05	2.877 (2)	166
O2W—H2WA···O1v	0.85	1.88	2.716 (2)	168
O2W—H2WB···O9vi	0.85	1.87	2.709 (2)	168
C16—H16A···O3	0.95	2.55	3.323 (2)	139

Fe1—O3	2.0101 (13)
Fe1—O8	2.0135 (14)
Fe1—N2	2.0392 (15)
Fe1—O6	2.0413 (13)
Fe1—N1	2.0478 (14)
Fe1—O1	2.0544 (13)

O3—Fe1—O8	95.80 (6)
O3—Fe1—N2	107.52 (6)
O8—Fe1—N2	76.88 (6)
O3—Fe1—O6	91.49 (5)
O8—Fe1—O6	152.40 (5)
N2—Fe1—O6	75.54 (6)
O3—Fe1—N1	76.40 (5)
O8—Fe1—N1	105.50 (6)
N2—Fe1—N1	175.34 (6)
O6—Fe1—N1	102.08 (5)
O3—Fe1—O1	151.34 (5)
O8—Fe1—O1	94.61 (5)
N2—Fe1—O1	100.83 (5)
O6—Fe1—O1	91.53 (5)
N1—Fe1—O1	75.10 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O2i	0.92	2.00	2.8431 (19)	152
N4—H4NA⋯O2Wii	0.92	2.04	2.957 (2)	173
N4—H4NB⋯O3	0.92	2.33	3.139 (2)	147
O5—H5⋯O1W	0.85	1.74	2.566 (2)	164
O10—H10⋯O2W	0.85	1.80	2.614 (2)	159
N5—H5NA⋯O2i	0.92	1.98	2.800 (2)	148
N5—H5NB⋯O6iii	0.92	1.96	2.832 (2)	157
O1W—H1WA⋯O7iv	0.85	1.98	2.826 (2)	173
O1W—H1WB⋯O4ii	0.85	2.05	2.877 (2)	166
O2W—H2WA⋯O1v	0.85	1.88	2.716 (2)	168
O2W—H2WB⋯O9vi	0.85	1.87	2.709 (2)	168
C16—H16A⋯O3	0.95	2.55	3.323 (2)	139

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