Crystal structure of a water oxidation catalyst solvate with composition (NH₄)₂[Fe^IV(L-6H)]·3CH₃COOH (L = clathrochelate ligand)

The coordination polyhedron of the complex [Fe^IV(C₁₂H₁₂N₁₂O₆)]²⁻ or [Fe^IV(L–6H)]²⁻ anions exhibits a shape inter­mediate between trigonal-prismatic and anti­prismatic.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in solvent or counterion
• R factor = 0.024
• wR factor = 0.064
• Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT312_ALERT_2_A Strange C-O-H Geometry (C-O  <   1.25 Ang) .....         O6 Check

Author Response: This is a false alert. O6 atom belongs to the C=O function of the carboxylic group of the disordered molecule of acetic acid and does not form O-H bonds. The instruction "FREE O6 H12c" in the .ins file as well as deleting the O6-H12c bond length from the CIF file did not have an effect.

Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.17 Note
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C5       - C5_a     .       1.53 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
                1  1  0,   2  0  0,  -1  1  1,   1  1  1,   0  0  2,

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          8 Report
              H2    H12A  H12B  H12C  H4    H15A  H15B  H15C
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00010 Ang.
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.          3 Note
PLAT300_ALERT_4_G Atom Site Occupancy of O2         Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O6         Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C12        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2         Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H12A       Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H12B       Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H12C       Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O4         Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O10        Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C15        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4         Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15A       Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15B       Constrained at       0.25 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15C       Constrained at       0.25 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12B     ..N1       .       2.66 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13E     ..N9       .       2.64 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13F     ..N11      .       2.63 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12B     ..N1       .       2.66 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13B     ..O5       .       2.67 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H13C     ..O8       .       2.63 Ang.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...      28.60 Deg.
              C15  -O4   -H15A    1_555   1_555   1_555 ......     #   84 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...      14.80 Deg.
              O6   -C12  -H12C    1_555   1_555   1_555 ......     #  100 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...       8.80 Deg.
              H15A -C15  -O4      1_555   1_555   1_555 ......     #  106 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...       0.00 Deg.
              H15A -C15  -H15A    1_555   1_555   1_555 ......     #  120 Check
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF ...       8.80 Deg.
              O4   -C15  -H15A    1_555   1_555   1_555 ......     #  122 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        92% Note
PLAT965_ALERT_2_G The SHELXL WEIGHT Optimisation has not Converged     Please Check
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..       68.1 Degree
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   1 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  37 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
  31 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Diammonium {µ-1,3,4,7,8,10,12,13,16,17,19,22-dodecaazatetracyclo[8.8.4.1^3,17.1^8,12]tetracosane-5,6,14,15,20,21-hexaonato}ferrate(IV) acetic acid trisolvate

Crystal data

(NH4)2[Fe(C12H12N12O6)]·3C2H4O2	F(000) = 1440
Mr = 692.42	Dx = 1.681 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.5352 (2) Å	Cell parameters from 18947 reflections
b = 11.5178 (1) Å	θ = 3.8–34.6°
c = 16.0472 (2) Å	µ = 0.64 mm^−1
β = 107.616 (2)°	T = 120 K
V = 2736.70 (6) Å^3	Block, black
Z = 4	0.45 × 0.20 × 0.13 mm

Data collection

Rigaku SuperNova, Single source at offset, Eos diffractometer	2431 independent reflections
Radiation source: micro-source	2345 reflections with I > 2σ(I)
Detector resolution: 16.0107 pixels mm^-1	Rint = 0.025
φ scans and ω scans with κ offset	θmax = 25.0°, θmin = 3.2°
Absorption correction: analytical [CrysAlisPro (Rigaku OD, 2015) based on analytical numerical absorption correction using a multifaceted crystal model (Clark & Reid, 1995)]	h = −18→18
Tmin = 0.888, Tmax = 0.954	k = −13→13
19869 measured reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.0287P)^2 + 4.4687P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2431 reflections	Δρmax = 0.31 e Å^−3
265 parameters	Δρmin = −0.30 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.500000	0.51456 (3)	0.750000	0.01084 (10)
O1	0.49183 (7)	0.33179 (10)	0.53250 (7)	0.0185 (3)
O3	0.67899 (8)	0.34064 (11)	0.94355 (8)	0.0230 (3)
O5	0.58025 (8)	0.84207 (10)	0.72496 (8)	0.0219 (3)
O7	0.58585 (9)	0.91495 (11)	1.02775 (9)	0.0309 (3)
O8	0.62188 (9)	0.74720 (11)	0.97758 (10)	0.0306 (3)
H8	0.5866 (19)	0.722 (2)	1.0013 (18)	0.054 (8)*
N1	0.54198 (8)	0.41708 (11)	0.66990 (8)	0.0140 (3)
N3	0.61583 (9)	0.47931 (11)	0.83762 (8)	0.0130 (3)
N5	0.55986 (8)	0.64326 (11)	0.71280 (8)	0.0137 (3)
N7	0.63190 (9)	0.42275 (12)	0.66460 (8)	0.0156 (3)
N9	0.69873 (9)	0.48505 (11)	0.81754 (8)	0.0148 (3)
N11	0.64693 (9)	0.63143 (12)	0.70168 (9)	0.0155 (3)
N13	0.63652 (10)	0.84256 (13)	0.56441 (10)	0.0185 (3)
H13D	0.6113 (14)	0.916 (2)	0.5469 (13)	0.028*
H13E	0.6955 (16)	0.8442 (18)	0.5665 (13)	0.028*
H13F	0.6296 (14)	0.8293 (18)	0.6159 (15)	0.028*
H13G	0.6080 (14)	0.789 (2)	0.5275 (14)	0.028*
C1	0.48051 (10)	0.37867 (13)	0.59867 (10)	0.0143 (3)
C3	0.61482 (10)	0.39725 (13)	0.89673 (10)	0.0149 (3)
C5	0.54073 (10)	0.75177 (14)	0.73270 (10)	0.0146 (3)
C7	0.69757 (10)	0.39761 (14)	0.74949 (10)	0.0162 (3)
H3A	0.758539	0.393247	0.742223	0.019*
H3B	0.683704	0.320624	0.769698	0.019*
C9	0.71270 (10)	0.60121 (14)	0.78697 (10)	0.0166 (3)
H4A	0.774496	0.605943	0.781768	0.020*
H4B	0.708119	0.658987	0.831114	0.020*
C11	0.64715 (11)	0.54171 (14)	0.63704 (10)	0.0173 (3)
H6A	0.705955	0.543798	0.624954	0.021*
H6B	0.599543	0.560094	0.581832	0.021*
C13	0.68764 (14)	0.91648 (18)	0.94181 (14)	0.0283 (4)
H13A	0.7117 (17)	0.984 (2)	0.9689 (16)	0.042*
H13B	0.6571 (16)	0.926 (2)	0.8850 (17)	0.042*
H13C	0.7317 (17)	0.867 (2)	0.9373 (15)	0.042*
C14	0.62703 (11)	0.86083 (15)	0.98682 (11)	0.0211 (4)
O2	0.5695 (5)	0.1300 (5)	0.6914 (4)	0.0264 (14)	0.25
H2	0.564306	0.114115	0.639008	0.040*	0.25
O4	0.4878 (4)	0.1137 (5)	0.6462 (5)	0.0307 (15)	0.25
H4	0.523622	0.105568	0.616529	0.046*	0.25
O6	0.4189 (3)	0.1429 (5)	0.6588 (4)	0.0316 (12)	0.25
O10	0.6091 (4)	0.1341 (5)	0.7634 (4)	0.0303 (12)	0.25
C12	0.4935 (6)	0.1199 (6)	0.7018 (6)	0.039 (2)	0.5
H12A	0.520573	0.050427	0.684862	0.058*	0.25
H12B	0.520573	0.189367	0.684862	0.058*	0.25
H12C	0.428294	0.119897	0.672332	0.058*	0.25
C15	0.5341 (6)	0.1169 (5)	0.7245 (7)	0.041 (2)	0.5
H15C	0.571635	0.047433	0.741920	0.061*	0.25
H15B	0.571635	0.186372	0.741920	0.061*	0.25
H15A	0.506375	0.116903	0.660900	0.061*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01181 (17)	0.01133 (17)	0.00910 (16)	0.000	0.00276 (12)	0.000
O1	0.0187 (6)	0.0216 (6)	0.0146 (6)	0.0041 (5)	0.0039 (4)	−0.0050 (5)
O3	0.0175 (6)	0.0266 (6)	0.0234 (6)	0.0029 (5)	0.0039 (5)	0.0125 (5)
O5	0.0253 (6)	0.0152 (6)	0.0282 (6)	−0.0036 (5)	0.0126 (5)	0.0001 (5)
O7	0.0368 (8)	0.0237 (7)	0.0423 (8)	−0.0063 (6)	0.0269 (7)	−0.0046 (6)
O8	0.0316 (7)	0.0218 (7)	0.0475 (8)	−0.0062 (6)	0.0254 (7)	−0.0035 (6)
N1	0.0126 (6)	0.0156 (7)	0.0138 (6)	0.0024 (5)	0.0038 (5)	−0.0008 (5)
N3	0.0114 (6)	0.0151 (6)	0.0120 (6)	−0.0015 (5)	0.0027 (5)	0.0009 (5)
N5	0.0130 (6)	0.0151 (7)	0.0149 (6)	0.0011 (5)	0.0067 (5)	0.0023 (5)
N7	0.0122 (6)	0.0197 (7)	0.0156 (7)	0.0035 (5)	0.0050 (5)	0.0006 (5)
N9	0.0117 (6)	0.0172 (7)	0.0153 (7)	−0.0006 (5)	0.0039 (5)	0.0019 (5)
N11	0.0132 (6)	0.0181 (7)	0.0170 (7)	0.0015 (5)	0.0074 (5)	0.0035 (5)
N13	0.0203 (8)	0.0174 (8)	0.0173 (7)	−0.0037 (6)	0.0048 (6)	−0.0026 (6)
C1	0.0174 (8)	0.0120 (7)	0.0128 (7)	0.0034 (6)	0.0033 (6)	0.0011 (6)
C3	0.0163 (8)	0.0149 (8)	0.0126 (7)	−0.0018 (6)	0.0033 (6)	−0.0007 (6)
C5	0.0160 (8)	0.0151 (8)	0.0115 (7)	−0.0003 (6)	0.0024 (6)	0.0012 (6)
C7	0.0143 (8)	0.0182 (8)	0.0159 (8)	0.0039 (6)	0.0041 (6)	0.0019 (6)
C9	0.0138 (7)	0.0178 (8)	0.0182 (8)	−0.0020 (6)	0.0049 (6)	0.0029 (6)
C11	0.0166 (8)	0.0221 (8)	0.0150 (8)	0.0036 (6)	0.0075 (6)	0.0031 (6)
C13	0.0318 (10)	0.0263 (10)	0.0330 (11)	−0.0074 (8)	0.0193 (9)	−0.0042 (8)
C14	0.0186 (8)	0.0230 (9)	0.0217 (9)	−0.0042 (7)	0.0058 (7)	−0.0019 (7)
O2	0.027 (4)	0.030 (3)	0.026 (4)	0.001 (2)	0.015 (3)	0.004 (2)
O4	0.031 (4)	0.035 (3)	0.030 (4)	0.005 (2)	0.015 (3)	0.004 (3)
O6	0.024 (3)	0.034 (3)	0.033 (3)	0.002 (2)	0.001 (3)	0.006 (2)
O10	0.024 (3)	0.035 (3)	0.033 (3)	−0.005 (2)	0.010 (3)	−0.003 (2)
C12	0.029 (4)	0.029 (3)	0.056 (7)	0.001 (3)	0.009 (4)	0.026 (3)
C15	0.041 (5)	0.015 (2)	0.053 (6)	−0.001 (3)	−0.005 (5)	0.007 (2)

Geometric parameters (Å, º)

Fe1—N1	1.9610 (13)	C7—H3B	0.9900
Fe1—N1^i	1.9610 (13)	C9—H4A	0.9900
Fe1—N3^i	1.9617 (13)	C9—H4B	0.9900
Fe1—N3	1.9617 (13)	C11—H6A	0.9900
Fe1—N5	1.9376 (13)	C11—H6B	0.9900
Fe1—N5^i	1.9376 (13)	C13—C14	1.493 (2)
O1—C1	1.2502 (19)	C13—H13A	0.92 (3)
O3—C3	1.2370 (19)	C13—H13B	0.90 (3)
O5—C5	1.2330 (19)	C13—H13C	0.91 (3)
O7—C14	1.218 (2)	O2—C12	1.246 (11)
O8—C14	1.317 (2)	O2—H2	0.8400
O8—H8	0.81 (3)	O2—H12A	1.1750
N1—C1	1.324 (2)	O2—H12B	1.0032
N1—N7	1.4266 (18)	O4—C15	1.244 (12)
N3—C3	1.342 (2)	O4—H4	0.8399
N3—N9	1.4205 (18)	O4—H15A	0.3140
N5—C5	1.345 (2)	O6—C12	1.186 (10)
N5—N11	1.4236 (17)	O6—H12C	0.3459
N7—C7	1.463 (2)	O10—C15	1.161 (10)
N7—C11	1.481 (2)	O10—H15C	1.1550
N9—C9	1.464 (2)	O10—H15B	0.8358
N9—C7	1.482 (2)	C12—C12^i	1.50 (2)
N11—C11	1.465 (2)	C12—H12A	0.9800
N11—C9	1.481 (2)	C12—H12B	0.9800
N13—H13D	0.94 (2)	C12—H12C	0.9802
N13—H13E	0.91 (2)	C15—H15A	0.9798
N13—H13F	0.88 (2)	C15—C15^i	1.52 (2)
N13—H13G	0.87 (2)	C15—H15C	0.9800
C1—C3^i	1.520 (2)	C15—H15B	0.9800
C5—C5^i	1.528 (3)	C15—H15A	0.9798
C7—H3A	0.9900
N5^i—Fe1—N1	157.78 (5)	N7—C11—H6A	108.8
N5—Fe1—N1^i	157.78 (5)	N11—C11—H6B	108.8
N5^i—Fe1—N1^i	87.15 (5)	N7—C11—H6B	108.8
N1—Fe1—N1^i	110.14 (8)	H6A—C11—H6B	107.7
N5—Fe1—N3^i	111.05 (5)	C14—C13—H13A	111.3 (15)
N5^i—Fe1—N3^i	87.56 (5)	C14—C13—H13B	109.2 (15)
N1^i—Fe1—N3^i	86.36 (5)	H13A—C13—H13B	113 (2)
N1—Fe1—N3	86.36 (5)	C14—C13—H13C	111.9 (15)
N1^i—Fe1—N3	80.01 (5)	H13A—C13—H13C	111 (2)
N1—Fe1—N5	87.15 (5)	H13B—C13—H13C	100 (2)
N5—Fe1—N3	87.56 (5)	O7—C14—O8	123.05 (16)
N1—Fe1—N3^i	80.01 (5)	O7—C14—C13	123.51 (17)
N5^i—Fe1—N3	111.05 (5)	O8—C14—C13	113.44 (15)
N5—Fe1—N5^i	80.18 (7)	C12—O2—H2	107.9
N3^i—Fe1—N3	156.12 (8)	C12—O2—H12A	47.6
C14—O8—H8	109 (2)	H2—O2—H12A	82.9
C1—N1—N7	115.28 (12)	C12—O2—H12B	50.2
C1—N1—Fe1	117.46 (10)	H2—O2—H12B	101.8
N7—N1—Fe1	122.60 (10)	H12A—O2—H12B	94.2
C3—N3—N9	113.47 (12)	C15—O4—H4	107.3
C3—N3—Fe1	116.60 (10)	C15—O4—H15A	28.6
N9—N3—Fe1	121.71 (9)	H4—O4—H15A	79.9
C5—N5—N11	113.90 (12)	C12—O6—H12C	46.5
C5—N5—Fe1	118.46 (10)	C15—O10—H15C	50.1
N11—N5—Fe1	121.89 (9)	C15—O10—H15B	56.0
N1—N7—C7	110.79 (12)	H15C—O10—H15B	105.9
N1—N7—C11	107.95 (11)	O6—C12—O2	134.3 (9)
C7—N7—C11	109.38 (12)	O6—C12—C12^i	113.8 (10)
N3—N9—C9	110.80 (12)	O2—C12—C12^i	107.6 (9)
N3—N9—C7	109.02 (12)	O6—C12—H12A	116.5
C9—N9—C7	110.14 (12)	O2—C12—H12A	62.4
N5—N11—C11	111.24 (12)	C12^i—C12—H12A	110.6
N5—N11—C9	108.82 (11)	O6—C12—H12B	94.6
C11—N11—C9	109.88 (12)	O2—C12—H12B	51.9
H13D—N13—H13E	108.6 (18)	C12^i—C12—H12B	110.6
H13D—N13—H13F	106.2 (18)	H12A—C12—H12B	109.5
H13E—N13—H13F	112.3 (18)	O6—C12—H12C	14.8
H13D—N13—H13G	110.3 (18)	O2—C12—H12C	144.8
H13E—N13—H13G	109.8 (19)	C12^i—C12—H12C	107.2
H13F—N13—H13G	109.6 (19)	H12A—C12—H12C	109.5
O1—C1—N1	128.86 (14)	H12B—C12—H12C	109.5
O1—C1—C3^i	119.45 (13)	H15A—C15—O10	127.8
N1—C1—C3^i	111.69 (13)	H15A—C15—O4	8.8
O3—C3—N3	128.37 (14)	O10—C15—O4	136.6 (10)
O3—C3—C1^i	120.94 (14)	H15A—C15—C15^i	113.7
N3—C3—C1^i	110.69 (13)	O10—C15—C15^i	117.4 (11)
O5—C5—N5	127.40 (14)	O4—C15—C15^i	105.1 (10)
O5—C5—C5^i	121.93 (9)	H15A—C15—H15C	109.5
N5—C5—C5^i	110.67 (8)	O10—C15—H15C	64.6
N7—C7—N9	113.67 (12)	O4—C15—H15C	112.1
N7—C7—H3A	108.8	C15^i—C15—H15C	107.3
N9—C7—H3A	108.8	H15A—C15—H15B	109.5
N7—C7—H3B	108.8	O10—C15—H15B	45.0
N9—C7—H3B	108.8	O4—C15—H15B	115.1
H3A—C7—H3B	107.7	C15^i—C15—H15B	107.3
N9—C9—N11	113.19 (13)	H15C—C15—H15B	109.5
N9—C9—H4A	108.9	H15A—C15—H15A	0.0
N11—C9—H4A	108.9	O10—C15—H15A	127.8
N9—C9—H4B	108.9	O4—C15—H15A	8.8
N11—C9—H4B	108.9	C15^i—C15—H15A	113.7
H4A—C9—H4B	107.8	H15C—C15—H15A	109.5
N11—C11—N7	113.98 (12)	H15B—C15—H15A	109.5
N11—C11—H6A	108.8
C1—N1—N7—C7	−146.37 (14)	N9—N3—C3—C1^i	−168.31 (12)
Fe1—N1—N7—C7	58.47 (15)	Fe1—N3—C3—C1^i	−19.18 (16)
C1—N1—N7—C11	93.89 (15)	N11—N5—C5—O5	15.8 (2)
Fe1—N1—N7—C11	−61.27 (14)	Fe1—N5—C5—O5	169.60 (13)
C3—N3—N9—C9	−154.44 (13)	N11—N5—C5—C5^i	−164.79 (14)
Fe1—N3—N9—C9	58.19 (15)	Fe1—N5—C5—C5^i	−11.0 (2)
C3—N3—N9—C7	84.19 (15)	N1—N7—C7—N9	−65.02 (16)
Fe1—N3—N9—C7	−63.18 (14)	C11—N7—C7—N9	53.87 (16)
C5—N5—N11—C11	−148.26 (13)	N3—N9—C7—N7	67.24 (16)
Fe1—N5—N11—C11	58.90 (15)	C9—N9—C7—N7	−54.54 (16)
C5—N5—N11—C9	90.56 (15)	N3—N9—C9—N11	−66.79 (16)
Fe1—N5—N11—C9	−62.28 (14)	C7—N9—C9—N11	53.92 (16)
N7—N1—C1—O1	11.1 (2)	N5—N11—C9—N9	68.10 (16)
Fe1—N1—C1—O1	167.61 (13)	C11—N11—C9—N9	−53.92 (16)
N7—N1—C1—C3^i	−168.97 (12)	N5—N11—C11—N7	−66.46 (16)
Fe1—N1—C1—C3^i	−12.47 (17)	C9—N11—C11—N7	54.10 (16)
N9—N3—C3—O3	11.7 (2)	N1—N7—C11—N11	66.44 (16)
Fe1—N3—C3—O3	160.86 (14)	C7—N7—C11—N11	−54.19 (16)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O7^ii	0.84	1.94	2.763 (6)	165
O2—H12B···N1	1.00	2.66	3.338 (6)	125
O2—H12A···O5^iii	1.17	2.58	3.356 (6)	122
O4—H4···O7^ii	0.84	1.96	2.792 (7)	169
O8—H8···O1^iv	0.81 (3)	1.80 (3)	2.6007 (17)	168 (3)
O10—H15C···O5^iii	1.15	2.39	3.425 (6)	148
N13—H13D···O7^v	0.94 (2)	1.99 (2)	2.913 (2)	166.4 (18)
N13—H13E···O3^vi	0.91 (2)	2.00 (2)	2.9073 (19)	173.2 (19)
N13—H13E···N9^vi	0.91 (2)	2.64 (2)	3.146 (2)	116.5 (16)
N13—H13F···O5	0.88 (2)	2.12 (2)	2.9606 (19)	160.7 (19)
N13—H13F···N11	0.88 (2)	2.63 (2)	3.252 (2)	128.3 (17)
N13—H13G···O1^vii	0.87 (2)	2.09 (2)	2.9241 (19)	158.8 (19)
N13—H13G···O3^ii	0.87 (2)	2.48 (2)	3.0698 (19)	125.0 (17)
C7—H3A···O5^viii	0.99	2.47	3.4109 (19)	159
C7—H3B···O10	0.99	2.43	3.366 (6)	158
C9—H4A···O2^vi	0.99	2.35	3.312 (7)	165
C9—H4A···O10^vi	0.99	2.17	3.132 (5)	165
C11—H6B···O1^vii	0.99	2.31	3.2606 (19)	160
C12—H12B···N1	0.98	2.66	3.575 (7)	155
C12—H12A···O5^iii	0.98	2.58	3.448 (7)	147
C13—H13B···O5	0.90 (3)	2.67 (3)	3.480 (2)	151 (2)
C13—H13C···O8^ix	0.91 (3)	2.63 (3)	3.416 (3)	146 (2)
C15—H15C···O5^iii	0.98	2.39	3.245 (6)	146

Symmetry codes: (ii) x, −y+1, z−1/2; (iii) x, y−1, z; (iv) x, −y+1, z+1/2; (v) x, −y+2, z−1/2; (vi) −x+3/2, y+1/2, −z+3/2; (vii) −x+1, −y+1, −z+1; (viii) −x+3/2, y−1/2, −z+3/2; (ix) −x+3/2, −y+3/2, −z+2.