Bis(μ-hydroxido-κ2O:O)bis[bis(5-car­boxy­pyridine-2-carboxyl­ato-κ2N,O2)iron(III)] dihydrate

Cao, W.

doi:10.1107/S1600536813029449

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page m625

doi:10.1107/S1600536813029449

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Bis(μ-hydroxido-κ²O:O)bis[bis(5-carboxypyridine-2-carboxylato-κ²N,O²)iron(III)] dihydrate

Wenhai Cao ^a ^*

^aQinghai HuangHe Hydropower Development Co. Ltd, New Energy Branch, Xining, 810008, People's Republic of China
^*Correspondence e-mail: caowh2000@163.com

(Received 18 October 2013; accepted 25 October 2013; online 31 October 2013)

The complete binuclear complex in [Fe₂(C₇H₄NO₄)₄(OH)₂]·2H₂O, is generated by the application twofold symmetry. The Fe^III atom is coordinated by the O atoms of two bridging hydroxyl groups and by two N and two O atoms from two pyridine-2,5-dicarboxylato ligands, forming a distorted octahedral geometry. The Fe⋯Fe separation within the dinuclear complex is 3.0657 (4) Å. In the crystal, O—H⋯O and C—H⋯O hydrogen-bonding interactions connect the molecules into a three-dimensional supramolecular network.

CCDC reference: 968712

Related literature

For background to the coordination modes of the pyridine-2,5-dicarboxylate ligand, see: Zhang et al. (2005 , 2006 ); Liang et al. (2000 ); Wibowo et al. (2011 ). For iron complexes of the pyridine-2,5-dicarboxylate ligand, see: Shi et al. (2011 ); Xu et al. (2004 ); Gao et al. (2005 ).

Experimental

Crystal data

[Fe₂(C₇H₄NO₄)₄(OH)₂]·2H₂O
M_r = 846.20
Monoclinic, P 2/c
a = 7.6130 (7) Å
b = 14.2716 (14) Å
c = 16.2594 (13) Å
β = 114.556 (4)°
V = 1606.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 298 K
0.28 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.767, T_max = 0.825
11029 measured reflections
3972 independent reflections
3224 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.01
3972 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O2ⁱ	0.82	1.98	2.761 (2)	160
O4—H4⋯O2ⁱⁱ	0.85	1.80	2.643 (2)	175
O9—H9A⋯O6ⁱⁱⁱ	0.86	1.91	2.735 (2)	162
O10—H10A⋯O5	0.87	2.34	2.914 (3)	124
O10—H10B⋯O7^iv	0.88	2.02	2.865 (3)	161
C3—H3⋯O7^v	0.93	2.36	3.223 (3)	155
C5—H5⋯O10ⁱⁱⁱ	0.93	2.54	3.465 (3)	174
C9—H9⋯O8^vi	0.93	2.53	3.425 (3)	162
Symmetry codes: (i) -x+2, -y, -z; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y, -z; (v) x, y+1, z; (vi) x-1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 968712

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813029449/rz5089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029449/rz5089Isup2.hkl

checkCIF report

Comment top

In the past few decades, pyridine-2,5-dicarboxylic acid (H₂pydc) has attracted considerable attention for its ability to coordinate to different metal centres. It can display different kinds of coordination modes, and the relative position of the coordinative moieties is adequate to form supramolecular structures of varied structural features (Zhang et al., 2006; Liang et al., 2000; Wibowo et al., 2011; Zhang et al., 2005). A number of compounds based on pyridine-2,5-dicarboxylic acid and transition metals have been reported, few of them containing Fe ions (Shi et al., 2011; Xu et al., 2004; Gao et al., 2005). Herein, the synthesis and crystal structure of a novel binuclear iron(III) derivative is reported.

As shown in Fig. 1, the metal is coordinated by two O atoms (O1, O5) and two N atoms (N3, N5) from two Hpydc^- ligands and two µ₂-OH groups (O9, O9A) to form a slightly distorted octahedral geometry. Two iron metals related by a two-fold axis are bridged by the OH groups to form a binuclear complex molecule. The mean Fe—O and Fe—N distances are 1.971 (9) Å and 2.114 (2) Å, respectively. In the crystal, the title compound features two kinds of hydrogen interactions (O—H···O and C—H···O; Table 1), which connect the binuclear units into a three-dimensional supramolecular network (Fig. 2).

Related literature top

For background to the coordination modes of the pyridine-2,5-dicarboxylate ligand, see: Zhang et al. (2005, 2006); Liang et al. (2000); Wibowo et al. (2011). For iron complexes of the pyridine-2,5-dicarboxylate ligand, see: Shi et al. (2011); Xu et al. (2004); Gao et al. (2005).

Experimental top

A mixture of pyridine-2,5-dicarboxylic acid (0.0335 g, 0.2 mmol), Sr(OH)₂·8H₂O (0.0267 g, 0.1 mmol), Fe(NO₃)₃·9H₂O (0.0404 g, 0.1 mmol), imidazole (0.0235 g, 0.35 mmol), and H₂O (3 ml, v/v = 2:1) was sealed in a Pyrex-tube (8 ml) and heated at 120°C for 2 days. The tube was then cooled to room temperature, generating bright-green rod crystals. Yield: 0.0237 g (56%, based on Fe). Elemental analysis calc. for C₂₈H₂₂Fe₂N₄O₂₀: C, 39.74; H, 2.62; N, 6.62%. Found: C, 39.66; H, 2.65; N, 6.69%.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids. Symmetry code: (A) -x + 2, y,-z + 1/2.
	Fig. 2. Crystal packing of the title compound viewed down the a axis. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.

Bis(µ-hydroxido-κ²O:O)bis[bis(5-carboxypyridine-2-carboxylato-κ²N,O²)iron(III)] dihydrate top

Crystal data top

[Fe₂(C₇H₄NO₄)₄(OH)₂]·2H₂O	F(000) = 860
M_r = 846.20	D_x = 1.749 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 3376 reflections
a = 7.6130 (7) Å	θ = 2.8–27.8°
b = 14.2716 (14) Å	µ = 1.00 mm⁻¹
c = 16.2594 (13) Å	T = 298 K
β = 114.556 (4)°	Rod, green
V = 1606.8 (3) Å³	0.28 × 0.25 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3972 independent reflections
Radiation source: fine-focus sealed tube	3224 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→9
T_min = 0.767, T_max = 0.825	k = −19→15
11029 measured reflections	l = −21→21

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0446P)² + 0.9967P] where P = (F_o² + 2F_c²)/3
3972 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Fe₂(C₇H₄NO₄)₄(OH)₂]·2H₂O	V = 1606.8 (3) Å³
M_r = 846.20	Z = 2
Monoclinic, P2/c	Mo Kα radiation
a = 7.6130 (7) Å	µ = 1.00 mm⁻¹
b = 14.2716 (14) Å	T = 298 K
c = 16.2594 (13) Å	0.28 × 0.25 × 0.20 mm
β = 114.556 (4)°

Data collection top

Bruker APEXII CCD diffractometer	3972 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3224 reflections with I > 2σ(I)
T_min = 0.767, T_max = 0.825	R_int = 0.026
11029 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.01	Δρ_max = 0.37 e Å⁻³
3972 reflections	Δρ_min = −0.47 e Å⁻³
244 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.80977 (4)	0.202541 (19)	0.164770 (19)	0.02479 (10)
O1	0.7658 (2)	0.21500 (10)	0.03507 (10)	0.0320 (3)
C1	0.7583 (3)	0.37700 (14)	0.06158 (13)	0.0276 (4)
O2	0.7390 (3)	0.30988 (11)	−0.07630 (11)	0.0422 (4)
C2	0.7485 (3)	0.46928 (15)	0.03644 (15)	0.0364 (5)
H2	0.7459	0.4859	−0.0194	0.044*
N3	0.7556 (2)	0.05572 (11)	0.14087 (12)	0.0270 (4)
C3	0.7427 (4)	0.53720 (16)	0.09617 (16)	0.0384 (5)
H3	0.7356	0.6003	0.0808	0.046*
O3	0.7248 (4)	0.66606 (13)	0.22363 (14)	0.0732 (7)
O4	0.7493 (4)	0.55104 (13)	0.31845 (12)	0.0619 (6)
H4	0.7432	0.5981	0.3492	0.093*
C4	0.7476 (3)	0.51062 (14)	0.17838 (14)	0.0311 (4)
O5	0.5359 (2)	0.19337 (10)	0.14846 (11)	0.0346 (3)
N5	0.7678 (2)	0.35085 (12)	0.14291 (11)	0.0264 (3)
C5	0.7609 (3)	0.41600 (14)	0.20041 (14)	0.0302 (4)
H5	0.7651	0.3978	0.2561	0.036*
O6	0.2935 (2)	0.09752 (13)	0.13321 (15)	0.0517 (5)
C6	0.7553 (3)	0.29598 (14)	0.00125 (14)	0.0281 (4)
O7	0.8655 (3)	−0.25246 (13)	0.07024 (15)	0.0579 (5)
C7	0.7401 (4)	0.58513 (16)	0.24209 (16)	0.0378 (5)
O8	1.1183 (3)	−0.15856 (12)	0.13517 (14)	0.0515 (5)
H8	1.1783	−0.2046	0.1309	0.077*
C8	0.5788 (3)	0.03170 (15)	0.13346 (15)	0.0308 (4)
O9	0.9102 (2)	0.20283 (10)	0.29588 (10)	0.0295 (3)
H9A	0.8474	0.1807	0.3246	0.044*
C9	0.5143 (4)	−0.05918 (16)	0.12100 (19)	0.0442 (6)
H9	0.3921	−0.0738	0.1172	0.053*
C10	0.6332 (3)	−0.12806 (16)	0.11428 (18)	0.0435 (6)
H10	0.5931	−0.1903	0.1065	0.052*
O10	0.2618 (4)	0.34823 (19)	0.09961 (18)	0.0971 (9)
H10A	0.2683	0.2904	0.1176	0.146*
H10B	0.1997	0.3279	0.0440	0.146*
C11	0.8133 (3)	−0.10417 (15)	0.11911 (15)	0.0322 (4)
C12	0.8722 (3)	−0.01115 (14)	0.13374 (14)	0.0288 (4)
H12	0.9945	0.0050	0.1387	0.035*
C13	0.4555 (3)	0.11238 (16)	0.13878 (15)	0.0333 (5)
C14	0.9348 (4)	−0.17947 (15)	0.10565 (17)	0.0376 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03269 (17)	0.01681 (15)	0.02696 (16)	0.00018 (11)	0.01447 (12)	0.00000 (11)
O1	0.0489 (9)	0.0203 (7)	0.0281 (7)	−0.0003 (6)	0.0173 (7)	−0.0018 (6)
C1	0.0343 (10)	0.0215 (9)	0.0284 (10)	0.0000 (8)	0.0144 (8)	−0.0006 (8)
O2	0.0745 (12)	0.0278 (8)	0.0328 (8)	0.0048 (7)	0.0309 (8)	0.0031 (6)
C2	0.0549 (14)	0.0255 (11)	0.0331 (11)	0.0019 (9)	0.0224 (10)	0.0029 (9)
N3	0.0325 (9)	0.0200 (8)	0.0313 (8)	−0.0020 (7)	0.0162 (7)	−0.0021 (7)
C3	0.0579 (14)	0.0200 (10)	0.0414 (12)	0.0024 (9)	0.0247 (11)	0.0012 (9)
O3	0.150 (2)	0.0244 (9)	0.0644 (13)	0.0098 (11)	0.0631 (15)	−0.0020 (9)
O4	0.1225 (18)	0.0296 (10)	0.0442 (10)	0.0052 (10)	0.0452 (12)	−0.0055 (8)
C4	0.0381 (11)	0.0210 (10)	0.0339 (11)	0.0019 (8)	0.0146 (9)	−0.0026 (8)
O5	0.0332 (8)	0.0254 (8)	0.0474 (9)	0.0016 (6)	0.0189 (7)	−0.0015 (6)
N5	0.0342 (9)	0.0195 (8)	0.0274 (8)	0.0024 (7)	0.0149 (7)	0.0011 (6)
C5	0.0399 (11)	0.0241 (10)	0.0285 (10)	0.0023 (8)	0.0163 (9)	−0.0009 (8)
O6	0.0397 (9)	0.0413 (10)	0.0850 (14)	−0.0057 (8)	0.0370 (9)	−0.0127 (10)
C6	0.0339 (10)	0.0232 (10)	0.0295 (10)	0.0004 (8)	0.0156 (8)	−0.0005 (8)
O7	0.0709 (13)	0.0267 (9)	0.0846 (14)	−0.0100 (8)	0.0409 (11)	−0.0218 (9)
C7	0.0531 (14)	0.0255 (11)	0.0384 (12)	0.0043 (9)	0.0226 (11)	−0.0029 (9)
O8	0.0502 (10)	0.0285 (9)	0.0842 (14)	0.0002 (8)	0.0364 (10)	−0.0146 (9)
C8	0.0354 (11)	0.0247 (10)	0.0371 (11)	−0.0025 (8)	0.0197 (9)	−0.0021 (9)
O9	0.0327 (7)	0.0322 (8)	0.0277 (7)	−0.0008 (6)	0.0168 (6)	0.0009 (6)
C9	0.0399 (13)	0.0293 (12)	0.0702 (17)	−0.0096 (10)	0.0295 (12)	−0.0064 (11)
C10	0.0444 (13)	0.0235 (11)	0.0650 (16)	−0.0095 (9)	0.0250 (12)	−0.0078 (11)
O10	0.141 (3)	0.0694 (18)	0.0912 (19)	0.0195 (17)	0.0580 (18)	−0.0053 (15)
C11	0.0399 (11)	0.0216 (10)	0.0360 (11)	−0.0012 (8)	0.0167 (9)	−0.0026 (9)
C12	0.0337 (10)	0.0214 (10)	0.0342 (10)	0.0000 (8)	0.0170 (9)	−0.0007 (8)
C13	0.0341 (11)	0.0315 (11)	0.0383 (11)	0.0001 (9)	0.0190 (9)	−0.0029 (9)
C14	0.0506 (14)	0.0219 (10)	0.0468 (13)	−0.0033 (9)	0.0268 (11)	−0.0038 (9)

Geometric parameters (Å, º) top

Fe1—O9	1.9427 (15)	C4—C7	1.502 (3)
Fe1—O9ⁱ	1.9543 (15)	O5—C13	1.287 (3)
Fe1—O5	1.9937 (15)	N5—C5	1.335 (3)
Fe1—O1	2.0011 (15)	C5—H5	0.9300
Fe1—N3	2.1397 (17)	O6—C13	1.217 (3)
Fe1—N5	2.1480 (17)	O7—C14	1.201 (3)
O1—C6	1.268 (2)	O8—C14	1.309 (3)
C1—N5	1.347 (3)	O8—H8	0.8200
C1—C2	1.372 (3)	C8—C9	1.372 (3)
C1—C6	1.510 (3)	C8—C13	1.511 (3)
O2—C6	1.231 (2)	O9—Fe1ⁱ	1.9543 (15)
C2—C3	1.386 (3)	O9—H9A	0.8554
C2—H2	0.9300	C9—C10	1.371 (3)
N3—C12	1.340 (3)	C9—H9	0.9300
N3—C8	1.345 (3)	C10—C11	1.383 (3)
C3—C4	1.375 (3)	C10—H10	0.9300
C3—H3	0.9300	O10—H10A	0.8695
O3—C7	1.187 (3)	O10—H10B	0.8773
O4—C7	1.308 (3)	C11—C12	1.390 (3)
O4—H4	0.8500	C11—C14	1.492 (3)
C4—C5	1.390 (3)	C12—H12	0.9300

O9—Fe1—O9ⁱ	76.25 (7)	N5—C5—C4	121.07 (19)
O9—Fe1—O5	93.39 (6)	N5—C5—H5	119.5
O9ⁱ—Fe1—O5	169.02 (6)	C4—C5—H5	119.5
O9—Fe1—O1	166.74 (6)	O2—C6—O1	123.53 (19)
O9ⁱ—Fe1—O1	91.53 (6)	O2—C6—C1	120.67 (18)
O5—Fe1—O1	99.10 (7)	O1—C6—C1	115.78 (18)
O9—Fe1—N3	99.19 (6)	O3—C7—O4	124.3 (2)
O9ⁱ—Fe1—N3	99.39 (6)	O3—C7—C4	122.8 (2)
O5—Fe1—N3	78.44 (6)	O4—C7—C4	112.89 (19)
O1—Fe1—N3	87.73 (6)	C14—O8—H8	109.5
O9—Fe1—N5	98.23 (6)	N3—C8—C9	122.5 (2)
O9ⁱ—Fe1—N5	96.84 (6)	N3—C8—C13	115.04 (18)
O5—Fe1—N5	88.13 (6)	C9—C8—C13	122.4 (2)
O1—Fe1—N5	77.87 (6)	Fe1—O9—Fe1ⁱ	103.75 (7)
N3—Fe1—N5	158.55 (7)	Fe1—O9—H9A	122.9
C6—O1—Fe1	119.39 (13)	Fe1ⁱ—O9—H9A	127.0
N5—C1—C2	122.20 (19)	C10—C9—C8	118.8 (2)
N5—C1—C6	113.94 (17)	C10—C9—H9	120.6
C2—C1—C6	123.85 (19)	C8—C9—H9	120.6
C1—C2—C3	118.4 (2)	C9—C10—C11	119.4 (2)
C1—C2—H2	120.8	C9—C10—H10	120.3
C3—C2—H2	120.8	C11—C10—H10	120.3
C12—N3—C8	118.98 (17)	H10A—O10—H10B	87.9
C12—N3—Fe1	128.94 (14)	C10—C11—C12	119.1 (2)
C8—N3—Fe1	112.08 (13)	C10—C11—C14	118.3 (2)
C4—C3—C2	119.5 (2)	C12—C11—C14	122.5 (2)
C4—C3—H3	120.3	N3—C12—C11	121.13 (19)
C2—C3—H3	120.3	N3—C12—H12	119.4
C7—O4—H4	105.7	C11—C12—H12	119.4
C3—C4—C5	119.2 (2)	O6—C13—O5	125.6 (2)
C3—C4—C7	118.80 (19)	O6—C13—C8	119.8 (2)
C5—C4—C7	122.0 (2)	O5—C13—C8	114.59 (18)
C13—O5—Fe1	119.57 (13)	O7—C14—O8	124.2 (2)
C5—N5—C1	119.53 (17)	O7—C14—C11	121.3 (2)
C5—N5—Fe1	128.09 (14)	O8—C14—C11	114.47 (19)
C1—N5—Fe1	112.28 (13)

O9—Fe1—O1—C6	−66.9 (3)	C3—C4—C5—N5	−0.4 (3)
O9ⁱ—Fe1—O1—C6	−89.41 (16)	C7—C4—C5—N5	−179.9 (2)
O5—Fe1—O1—C6	93.34 (16)	Fe1—O1—C6—O2	175.93 (17)
N3—Fe1—O1—C6	171.25 (16)	Fe1—O1—C6—C1	−5.7 (2)
N5—Fe1—O1—C6	7.26 (16)	N5—C1—C6—O2	177.1 (2)
N5—C1—C2—C3	−1.9 (3)	C2—C1—C6—O2	−1.7 (3)
C6—C1—C2—C3	176.8 (2)	N5—C1—C6—O1	−1.3 (3)
O9—Fe1—N3—C12	−91.72 (18)	C2—C1—C6—O1	179.9 (2)
O9ⁱ—Fe1—N3—C12	−14.28 (18)	C3—C4—C7—O3	2.1 (4)
O5—Fe1—N3—C12	176.66 (19)	C5—C4—C7—O3	−178.5 (3)
O1—Fe1—N3—C12	76.90 (18)	C3—C4—C7—O4	−178.8 (2)
N5—Fe1—N3—C12	124.4 (2)	C5—C4—C7—O4	0.7 (3)
O9—Fe1—N3—C8	87.60 (15)	C12—N3—C8—C9	1.6 (3)
O9ⁱ—Fe1—N3—C8	165.05 (14)	Fe1—N3—C8—C9	−177.8 (2)
O5—Fe1—N3—C8	−4.01 (14)	C12—N3—C8—C13	−177.72 (18)
O1—Fe1—N3—C8	−103.78 (15)	Fe1—N3—C8—C13	2.9 (2)
N5—Fe1—N3—C8	−56.3 (2)	O9ⁱ—Fe1—O9—Fe1ⁱ	−0.25 (9)
C1—C2—C3—C4	0.2 (4)	O5—Fe1—O9—Fe1ⁱ	176.08 (6)
C2—C3—C4—C5	0.9 (4)	O1—Fe1—O9—Fe1ⁱ	−23.5 (3)
C2—C3—C4—C7	−179.6 (2)	N3—Fe1—O9—Fe1ⁱ	97.25 (7)
O9—Fe1—O5—C13	−93.78 (17)	N5—Fe1—O9—Fe1ⁱ	−95.32 (7)
O9ⁱ—Fe1—O5—C13	−74.7 (4)	N3—C8—C9—C10	−1.1 (4)
O1—Fe1—O5—C13	90.68 (17)	C13—C8—C9—C10	178.1 (2)
N3—Fe1—O5—C13	4.91 (16)	C8—C9—C10—C11	−0.8 (4)
N5—Fe1—O5—C13	168.08 (17)	C9—C10—C11—C12	2.2 (4)
C2—C1—N5—C5	2.4 (3)	C9—C10—C11—C14	−176.1 (2)
C6—C1—N5—C5	−176.44 (18)	C8—N3—C12—C11	−0.1 (3)
C2—C1—N5—Fe1	−174.31 (18)	Fe1—N3—C12—C11	179.16 (15)
C6—C1—N5—Fe1	6.9 (2)	C10—C11—C12—N3	−1.7 (3)
O9—Fe1—N5—C5	−16.69 (18)	C14—C11—C12—N3	176.5 (2)
O9ⁱ—Fe1—N5—C5	−93.71 (18)	Fe1—O5—C13—O6	175.8 (2)
O5—Fe1—N5—C5	76.46 (18)	Fe1—O5—C13—C8	−4.7 (3)
O1—Fe1—N5—C5	176.19 (19)	N3—C8—C13—O6	−179.6 (2)
N3—Fe1—N5—C5	127.3 (2)	C9—C8—C13—O6	1.1 (4)
O9—Fe1—N5—C1	159.65 (14)	N3—C8—C13—O5	0.9 (3)
O9ⁱ—Fe1—N5—C1	82.63 (14)	C9—C8—C13—O5	−178.4 (2)
O5—Fe1—N5—C1	−107.19 (14)	C10—C11—C14—O7	18.1 (4)
O1—Fe1—N5—C1	−7.47 (14)	C12—C11—C14—O7	−160.1 (2)
N3—Fe1—N5—C1	−56.3 (2)	C10—C11—C14—O8	−162.0 (2)
C1—N5—C5—C4	−1.2 (3)	C12—C11—C14—O8	19.8 (3)
Fe1—N5—C5—C4	174.93 (15)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O2ⁱⁱ	0.82	1.98	2.761 (2)	160
O4—H4···O2ⁱⁱⁱ	0.85	1.80	2.643 (2)	175
O9—H9A···O6^iv	0.86	1.91	2.735 (2)	162
O10—H10A···O5	0.87	2.34	2.914 (3)	124
O10—H10B···O7^v	0.88	2.02	2.865 (3)	161
C3—H3···O7^vi	0.93	2.36	3.223 (3)	155
C5—H5···O10^iv	0.93	2.54	3.465 (3)	174
C9—H9···O8^vii	0.93	2.53	3.425 (3)	162

Symmetry codes: (ii) −x+2, −y, −z; (iii) x, −y+1, z+1/2; (iv) −x+1, y, −z+1/2; (v) −x+1, −y, −z; (vi) x, y+1, z; (vii) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O2ⁱ	0.82	1.98	2.761 (2)	160.1
O4—H4···O2ⁱⁱ	0.85	1.80	2.643 (2)	174.5
O9—H9A···O6ⁱⁱⁱ	0.86	1.91	2.735 (2)	162.0
O10—H10A···O5	0.87	2.34	2.914 (3)	123.8
O10—H10B···O7^iv	0.88	2.02	2.865 (3)	160.7
C3—H3···O7^v	0.93	2.36	3.223 (3)	154.5
C5—H5···O10ⁱⁱⁱ	0.93	2.54	3.465 (3)	174.0
C9—H9···O8^vi	0.93	2.53	3.425 (3)	161.6

Symmetry codes: (i) −x+2, −y, −z; (ii) x, −y+1, z+1/2; (iii) −x+1, y, −z+1/2; (iv) −x+1, −y, −z; (v) x, y+1, z; (vi) x−1, y, z.

Acknowledgements

This work was supported financially by the HuangHe Hydropower Development Co. Ltd, Qinghai.

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