fac-Tris(4-amino-benzohydroxamato)iron(III) ethanol solvate.

In the structure of the title compound, [Fe(C(7)H(7)N(2)O(2))(3)]·CH(3)CH(2)OH, the Fe(III) atom is in a distorted octa-hedral O(6) environment with the three hydroxamate O atoms (and the three carbonyl O atoms) arranged in a fac configuration and one of the hydroxamate ligands being puckered. The methyl C atom of the ethanol solvent mol-ecule is disordered over two positions with occupancies of 0.626 (13) and 0.374 (13), respectively. The cocrystallized ethanol mol-ecule is hydrogen bonded to one of the hydroxamate O atoms. O-H⋯O and N-H⋯O inter-actions generate infinite three-dimensional networks along [100], [010] and [001].

Related literature

For a detailed account of the mol­ecular and crystal structures of related tris­(hydroxamato)FeIII complexes, see: Rio-Echevarria et al. (2008 ▶); Mulcahy et al. (2007 ▶); Marmion et al. (2000 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶); for pseudorotation parameters, see: Rao et al. (1981 ▶).

Experimental

Crystal data

[Fe(C7H7N2O2)3]·C2H6O

M = 555.36

Triclinic,

a = 10.6232 (18) Å

b = 10.6455 (18) Å

c = 13.225 (2) Å

α = 107.550 (3)°

β = 91.085 (4)°

γ = 112.217 (3)°

V = 1305.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.63 mm−1

T = 100 K

0.30 × 0.20 × 0.03 mm

Data collection

Bruker SMART CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.883, T max = 0.981

24614 measured reflections

5739 independent reflections

5065 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.094

S = 1.06

5739 reflections

433 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002413X/sj5023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002413X/sj5023Isup2.hkl

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

[Fe(C7H7N2O2)3]·C2H6O	Z = 2
Mr = 555.36	F(000) = 578
Triclinic, P1	Dx = 1.413 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6232 (18) Å	Cell parameters from 4743 reflections
b = 10.6455 (18) Å	θ = 2.2–24.9°
c = 13.225 (2) Å	µ = 0.63 mm−1
α = 107.550 (3)°	T = 100 K
β = 91.085 (4)°	Plate, red
γ = 112.217 (3)°	0.30 × 0.20 × 0.03 mm
V = 1305.1 (4) Å3

Bruker SMART CCD area detector diffractometer	5739 independent reflections
Radiation source: fine-focus sealed tube	5065 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 8.366 pixels mm-1	θmax = 27.1°, θmin = 1.6°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −13→13
Tmin = 0.883, Tmax = 0.981	l = −16→16
24614 measured reflections

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0438P)2 + 0.6552P] where P = (Fo2 + 2Fc2)/3
5739 reflections	(Δ/σ)max = 0.004
433 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.31 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	Occ. (<1)
Fe	0.13879 (3)	0.36163 (3)	0.16284 (2)	0.01220 (9)
O2	0.06647 (14)	0.16143 (14)	0.06621 (11)	0.0180 (3)
N1	−0.05305 (18)	0.07800 (18)	0.09477 (14)	0.0187 (4)
H1N1	−0.087 (3)	−0.007 (3)	0.052 (2)	0.035 (7)*
C1	−0.0862 (2)	0.1334 (2)	0.18804 (16)	0.0161 (4)
O1	−0.01237 (14)	0.26557 (14)	0.24206 (11)	0.0162 (3)
C2	−0.2049 (2)	0.0445 (2)	0.22618 (16)	0.0179 (4)
C3	−0.2669 (2)	0.1117 (2)	0.30398 (18)	0.0239 (5)
H3	−0.231 (3)	0.211 (3)	0.331 (2)	0.039 (7)*
C4	−0.3816 (2)	0.0325 (3)	0.3394 (2)	0.0279 (5)
H4	−0.425 (3)	0.078 (3)	0.391 (2)	0.031 (7)*
C5	−0.4376 (2)	−0.1172 (2)	0.29942 (18)	0.0243 (5)
N2	−0.5509 (2)	−0.1970 (3)	0.3375 (2)	0.0340 (5)
H1N2	−0.595 (3)	−0.277 (3)	0.296 (2)	0.040 (9)*
H2N2	−0.602 (3)	−0.147 (3)	0.364 (2)	0.048 (9)*
C6	−0.3739 (3)	−0.1848 (2)	0.2234 (2)	0.0317 (5)
H6	−0.410 (3)	−0.288 (3)	0.198 (2)	0.043 (8)*
C7	−0.2604 (2)	−0.1056 (2)	0.1865 (2)	0.0286 (5)
H7	−0.219 (3)	−0.152 (3)	0.136 (2)	0.037 (7)*
O4	0.04007 (15)	0.41933 (14)	0.06861 (11)	0.0175 (3)
N3	0.03983 (18)	0.55267 (18)	0.11997 (14)	0.0188 (4)
H1N3	0.008 (3)	0.585 (3)	0.078 (2)	0.029 (7)*
C8	0.1040 (2)	0.6232 (2)	0.21800 (15)	0.0146 (4)
O3	0.15716 (14)	0.56033 (14)	0.26357 (10)	0.0149 (3)
C9	0.1150 (2)	0.7704 (2)	0.27167 (16)	0.0154 (4)
C10	0.1173 (2)	0.8613 (2)	0.21373 (17)	0.0196 (4)
H10	0.116 (2)	0.832 (2)	0.1403 (18)	0.014 (5)*
C11	0.1315 (2)	1.0008 (2)	0.26579 (17)	0.0205 (4)
H11	0.135 (2)	1.060 (2)	0.2244 (17)	0.015 (5)*
C12	0.1403 (2)	1.0527 (2)	0.37769 (17)	0.0184 (4)
N4	0.1479 (2)	1.1887 (2)	0.42768 (17)	0.0238 (4)
H1N4	0.165 (3)	1.217 (3)	0.494 (2)	0.027 (7)*
H2N4	0.161 (3)	1.247 (3)	0.388 (2)	0.042 (8)*
C13	0.1409 (2)	0.9625 (2)	0.43591 (17)	0.0182 (4)
H13	0.148 (2)	0.995 (3)	0.508 (2)	0.024 (6)*
C14	0.1295 (2)	0.8241 (2)	0.38380 (16)	0.0168 (4)
H14	0.129 (2)	0.765 (2)	0.4247 (17)	0.010 (5)*
O6	0.30277 (14)	0.41024 (15)	0.09015 (11)	0.0178 (3)
N5	0.41597 (18)	0.41538 (19)	0.14684 (14)	0.0173 (4)
H1N5	0.480 (2)	0.412 (2)	0.1112 (18)	0.016 (6)*
C15	0.4028 (2)	0.3985 (2)	0.24097 (15)	0.0145 (4)
O5	0.28464 (14)	0.37299 (14)	0.27232 (11)	0.0157 (3)
C16	0.5226 (2)	0.4146 (2)	0.30955 (15)	0.0154 (4)
C17	0.5013 (2)	0.3612 (2)	0.39495 (16)	0.0178 (4)
H17	0.408 (2)	0.311 (2)	0.4045 (18)	0.021 (6)*
C18	0.6104 (2)	0.3822 (2)	0.46526 (16)	0.0175 (4)
H18	0.592 (2)	0.346 (3)	0.5211 (19)	0.024 (6)*
C19	0.7457 (2)	0.4587 (2)	0.45299 (15)	0.0158 (4)
N6	0.8551 (2)	0.4808 (2)	0.52404 (15)	0.0198 (4)
H1N6	0.835 (2)	0.467 (2)	0.5823 (18)	0.008 (5)*
H2N6	0.927 (3)	0.549 (3)	0.529 (2)	0.037 (8)*
C20	0.7675 (2)	0.5081 (2)	0.36565 (17)	0.0186 (4)
H20	0.854 (2)	0.559 (2)	0.3568 (17)	0.015 (5)*
C21	0.6581 (2)	0.4880 (2)	0.29572 (17)	0.0187 (4)
H21	0.677 (2)	0.527 (2)	0.2400 (17)	0.012 (5)*
O7	0.62865 (18)	0.41913 (19)	0.03203 (14)	0.0300 (4)
H1O7	0.651 (3)	0.473 (3)	0.000 (2)	0.030 (7)*
C22	0.6632 (3)	0.2992 (3)	−0.0101 (2)	0.0450 (7)
H22A	0.7633	0.3304	0.0097	0.054*	0.626 (13)
H22B	0.6425	0.2649	−0.0893	0.054*	0.626 (13)
H22C	0.5911	0.2283	−0.0711	0.054*	0.374 (13)
H22D	0.7502	0.3321	−0.0395	0.054*	0.374 (13)
C23A	0.5904 (9)	0.1809 (6)	0.0278 (5)	0.048 (2)	0.626 (13)
H23A	0.5992	0.2168	0.1062	0.073*	0.626 (13)
H23B	0.6297	0.1088	0.0061	0.073*	0.626 (13)
H23C	0.4929	0.1371	−0.0032	0.073*	0.626 (13)
C23B	0.6799 (14)	0.2255 (11)	0.0608 (8)	0.052 (3)	0.374 (13)
H23D	0.7001	0.1432	0.0207	0.077*	0.374 (13)
H23E	0.5950	0.1914	0.0912	0.077*	0.374 (13)
H23F	0.7561	0.2917	0.1189	0.077*	0.374 (13)

	U11	U22	U33	U12	U13	U23
Fe	0.01437 (15)	0.00964 (14)	0.01186 (14)	0.00477 (11)	0.00097 (10)	0.00273 (10)
O2	0.0186 (7)	0.0124 (7)	0.0189 (7)	0.0040 (6)	0.0068 (6)	0.0023 (6)
N1	0.0189 (9)	0.0108 (8)	0.0199 (9)	0.0027 (7)	0.0037 (7)	0.0002 (7)
C1	0.0155 (9)	0.0125 (9)	0.0187 (10)	0.0061 (8)	0.0006 (8)	0.0028 (8)
O1	0.0176 (7)	0.0102 (6)	0.0168 (7)	0.0036 (5)	0.0032 (5)	0.0015 (5)
C2	0.0178 (10)	0.0148 (10)	0.0201 (10)	0.0057 (8)	0.0022 (8)	0.0058 (8)
C3	0.0252 (11)	0.0143 (10)	0.0286 (12)	0.0054 (9)	0.0085 (9)	0.0052 (9)
C4	0.0281 (12)	0.0259 (12)	0.0317 (13)	0.0118 (10)	0.0146 (10)	0.0106 (10)
C5	0.0181 (10)	0.0253 (11)	0.0301 (12)	0.0043 (9)	0.0001 (9)	0.0161 (10)
N2	0.0229 (11)	0.0333 (13)	0.0448 (14)	0.0024 (10)	0.0056 (10)	0.0229 (11)
C6	0.0296 (13)	0.0151 (11)	0.0439 (15)	0.0021 (10)	0.0070 (11)	0.0099 (10)
C7	0.0299 (12)	0.0150 (10)	0.0382 (14)	0.0087 (9)	0.0126 (11)	0.0051 (10)
O4	0.0266 (8)	0.0127 (7)	0.0132 (7)	0.0111 (6)	−0.0023 (6)	0.0004 (5)
N3	0.0263 (9)	0.0166 (9)	0.0158 (9)	0.0130 (7)	−0.0014 (7)	0.0033 (7)
C8	0.0161 (9)	0.0137 (9)	0.0142 (9)	0.0061 (8)	0.0024 (7)	0.0050 (7)
O3	0.0191 (7)	0.0115 (6)	0.0140 (7)	0.0063 (5)	−0.0011 (5)	0.0038 (5)
C9	0.0161 (9)	0.0143 (9)	0.0161 (9)	0.0073 (8)	0.0018 (7)	0.0041 (8)
C10	0.0257 (11)	0.0190 (10)	0.0162 (10)	0.0112 (9)	0.0029 (8)	0.0060 (8)
C11	0.0253 (11)	0.0186 (10)	0.0231 (11)	0.0117 (9)	0.0041 (9)	0.0108 (9)
C12	0.0146 (9)	0.0151 (10)	0.0256 (11)	0.0063 (8)	0.0057 (8)	0.0065 (8)
N4	0.0326 (11)	0.0153 (9)	0.0239 (11)	0.0109 (8)	0.0077 (8)	0.0050 (8)
C13	0.0202 (10)	0.0168 (10)	0.0151 (10)	0.0065 (8)	0.0036 (8)	0.0032 (8)
C14	0.0185 (10)	0.0144 (9)	0.0181 (10)	0.0062 (8)	0.0028 (8)	0.0069 (8)
O6	0.0160 (7)	0.0245 (8)	0.0167 (7)	0.0092 (6)	0.0019 (6)	0.0105 (6)
N5	0.0152 (8)	0.0225 (9)	0.0181 (9)	0.0091 (7)	0.0045 (7)	0.0102 (7)
C15	0.0175 (10)	0.0103 (9)	0.0162 (9)	0.0063 (7)	0.0027 (8)	0.0042 (7)
O5	0.0158 (7)	0.0171 (7)	0.0160 (7)	0.0071 (6)	0.0025 (5)	0.0073 (6)
C16	0.0180 (10)	0.0141 (9)	0.0159 (9)	0.0086 (8)	0.0028 (8)	0.0046 (8)
C17	0.0181 (10)	0.0159 (10)	0.0202 (10)	0.0070 (8)	0.0052 (8)	0.0068 (8)
C18	0.0227 (10)	0.0196 (10)	0.0151 (10)	0.0109 (8)	0.0047 (8)	0.0094 (8)
C19	0.0195 (10)	0.0141 (9)	0.0141 (9)	0.0102 (8)	0.0022 (8)	0.0007 (7)
N6	0.0197 (10)	0.0247 (10)	0.0168 (9)	0.0100 (8)	0.0037 (7)	0.0083 (8)
C20	0.0142 (10)	0.0190 (10)	0.0209 (10)	0.0046 (8)	0.0045 (8)	0.0069 (8)
C21	0.0198 (10)	0.0203 (10)	0.0171 (10)	0.0069 (8)	0.0043 (8)	0.0092 (8)
O7	0.0367 (10)	0.0372 (10)	0.0326 (9)	0.0221 (8)	0.0197 (8)	0.0238 (8)
C22	0.0638 (19)	0.0503 (17)	0.0404 (16)	0.0374 (16)	0.0226 (14)	0.0222 (14)
C23A	0.063 (5)	0.036 (3)	0.058 (4)	0.026 (3)	0.021 (3)	0.023 (3)
C23B	0.048 (7)	0.039 (5)	0.069 (6)	0.022 (5)	−0.016 (5)	0.015 (4)

Fe—O2	1.9615 (14)	N4—H1N4	0.83 (3)
Fe—O6	1.9769 (14)	N4—H2N4	0.90 (3)
Fe—O4	1.9822 (14)	C13—C14	1.382 (3)
Fe—O5	2.0444 (14)	C13—H13	0.90 (2)
Fe—O1	2.0470 (14)	C14—H14	0.94 (2)
Fe—O3	2.0654 (13)	O6—N5	1.379 (2)
O2—N1	1.383 (2)	N5—C15	1.313 (3)
N1—C1	1.315 (3)	N5—H1N5	0.84 (2)
N1—H1N1	0.84 (3)	C15—O5	1.285 (2)
C1—O1	1.282 (2)	C15—C16	1.474 (3)
C1—C2	1.466 (3)	C16—C17	1.396 (3)
C2—C3	1.394 (3)	C16—C21	1.400 (3)
C2—C7	1.396 (3)	C17—C18	1.377 (3)
C3—C4	1.378 (3)	C17—H17	0.96 (2)
C3—H3	0.93 (3)	C18—C19	1.400 (3)
C4—C5	1.391 (3)	C18—H18	0.92 (2)
C4—H4	0.94 (3)	C19—N6	1.381 (3)
C5—N2	1.390 (3)	C19—C20	1.396 (3)
C5—C6	1.395 (3)	N6—H1N6	0.84 (2)
N2—H1N2	0.80 (3)	N6—H2N6	0.82 (3)
N2—H2N2	0.90 (3)	C20—C21	1.380 (3)
C6—C7	1.380 (3)	C20—H20	0.90 (2)
C6—H6	0.96 (3)	C21—H21	0.94 (2)
C7—H7	0.92 (3)	O7—C22	1.417 (3)
O4—N3	1.378 (2)	O7—H1O7	0.78 (3)
N3—C8	1.304 (3)	C22—C23B	1.438 (8)
N3—H1N3	0.86 (3)	C22—C23A	1.446 (5)
C8—O3	1.283 (2)	C22—H22A	0.9900
C8—C9	1.470 (3)	C22—H22B	0.9900
C9—C10	1.398 (3)	C22—H22C	0.9900
C9—C14	1.401 (3)	C22—H22D	0.9900
C10—C11	1.382 (3)	C23A—H23A	0.9800
C10—H10	0.92 (2)	C23A—H23B	0.9800
C11—C12	1.402 (3)	C23A—H23C	0.9800
C11—H11	0.95 (2)	C23B—H23D	0.9800
C12—N4	1.368 (3)	C23B—H23E	0.9800
C12—C13	1.402 (3)	C23B—H23F	0.9800
O2—Fe—O6	90.72 (6)	C12—C13—H13	119.8 (15)
O2—Fe—O4	92.73 (6)	C13—C14—C9	120.68 (18)
O6—Fe—O4	91.70 (6)	C13—C14—H14	119.0 (13)
O2—Fe—O5	104.13 (6)	C9—C14—H14	120.3 (13)
O6—Fe—O5	78.92 (5)	N5—O6—Fe	112.13 (11)
O4—Fe—O5	160.68 (6)	C15—N5—O6	117.38 (16)
O2—Fe—O1	79.40 (5)	C15—N5—H1N5	127.0 (15)
O6—Fe—O1	162.99 (6)	O6—N5—H1N5	114.4 (15)
O4—Fe—O1	102.49 (6)	O5—C15—N5	118.19 (17)
O5—Fe—O1	90.01 (6)	O5—C15—C16	121.59 (17)
O2—Fe—O3	163.96 (6)	N5—C15—C16	120.18 (17)
O6—Fe—O3	102.91 (6)	C15—O5—Fe	113.19 (12)
O4—Fe—O3	78.63 (5)	C17—C16—C21	118.42 (18)
O5—Fe—O3	86.98 (5)	C17—C16—C15	119.09 (18)
O1—Fe—O3	89.21 (5)	C21—C16—C15	122.41 (18)
N1—O2—Fe	111.18 (11)	C18—C17—C16	121.01 (19)
C1—N1—O2	117.85 (16)	C18—C17—H17	120.6 (14)
C1—N1—H1N1	129.3 (18)	C16—C17—H17	118.4 (14)
O2—N1—H1N1	112.1 (18)	C17—C18—C19	120.58 (19)
O1—C1—N1	117.72 (18)	C17—C18—H18	118.3 (15)
O1—C1—C2	122.48 (17)	C19—C18—H18	121.1 (15)
N1—C1—C2	119.79 (17)	N6—C19—C20	120.91 (19)
C1—O1—Fe	112.64 (12)	N6—C19—C18	120.57 (19)
C3—C2—C7	118.2 (2)	C20—C19—C18	118.49 (18)
C3—C2—C1	119.10 (18)	C19—N6—H1N6	115.4 (14)
C7—C2—C1	122.69 (19)	C19—N6—H2N6	117 (2)
C4—C3—C2	121.1 (2)	H1N6—N6—H2N6	115 (2)
C4—C3—H3	119.6 (17)	C21—C20—C19	120.82 (19)
C2—C3—H3	119.3 (17)	C21—C20—H20	119.1 (14)
C3—C4—C5	120.8 (2)	C19—C20—H20	119.9 (14)
C3—C4—H4	121.3 (16)	C20—C21—C16	120.62 (19)
C5—C4—H4	117.9 (16)	C20—C21—H21	118.1 (13)
N2—C5—C4	120.7 (2)	C16—C21—H21	121.3 (13)
N2—C5—C6	121.0 (2)	C22—O7—H1O7	113 (2)
C4—C5—C6	118.3 (2)	O7—C22—C23B	118.2 (4)
C5—N2—H1N2	114 (2)	O7—C22—C23A	113.5 (3)
C5—N2—H2N2	112.1 (19)	C23B—C22—C23A	37.0 (4)
H1N2—N2—H2N2	114 (3)	O7—C22—H22A	108.9
C7—C6—C5	121.0 (2)	C23B—C22—H22A	73.0
C7—C6—H6	120.4 (17)	C23A—C22—H22A	108.9
C5—C6—H6	118.6 (17)	O7—C22—H22B	108.9
C6—C7—C2	120.6 (2)	C23B—C22—H22B	129.9
C6—C7—H7	120.1 (17)	C23A—C22—H22B	108.9
C2—C7—H7	119.2 (17)	H22A—C22—H22B	107.7
N3—O4—Fe	111.77 (11)	O7—C22—H22C	107.7
C8—N3—O4	118.68 (16)	C23B—C22—H22C	107.9
C8—N3—H1N3	127.3 (17)	C23A—C22—H22C	75.6
O4—N3—H1N3	113.2 (17)	H22A—C22—H22C	136.9
O3—C8—N3	117.74 (17)	H22B—C22—H22C	37.7
O3—C8—C9	122.39 (17)	O7—C22—H22D	107.7
N3—C8—C9	119.87 (17)	C23B—C22—H22D	107.6
C8—O3—Fe	113.04 (12)	C23A—C22—H22D	135.6
C10—C9—C14	118.69 (18)	H22A—C22—H22D	39.5
C10—C9—C8	121.53 (18)	H22B—C22—H22D	71.1
C14—C9—C8	119.73 (17)	H22C—C22—H22D	107.1
C11—C10—C9	120.73 (19)	C22—C23A—H22C	38.6
C11—C10—H10	118.5 (13)	C22—C23A—H23A	109.5
C9—C10—H10	120.7 (13)	H22C—C23A—H23A	142.0
C10—C11—C12	120.61 (19)	C22—C23A—H23B	109.5
C10—C11—H11	118.6 (13)	H22C—C23A—H23B	102.8
C12—C11—H11	120.8 (13)	C22—C23A—H23C	109.5
N4—C12—C13	121.5 (2)	H22C—C23A—H23C	76.8
N4—C12—C11	119.96 (19)	C22—C23B—H23D	109.5
C13—C12—C11	118.58 (18)	C22—C23B—H23E	109.5
C12—N4—H1N4	114.5 (18)	H23D—C23B—H23E	109.5
C12—N4—H2N4	117.8 (18)	C22—C23B—H23F	109.5
H1N4—N4—H2N4	125 (3)	H23D—C23B—H23F	109.5
C14—C13—C12	120.63 (19)	H23E—C23B—H23F	109.5
C14—C13—H13	119.5 (15)
O6—Fe—O2—N1	175.55 (12)	O3—C8—C9—C10	149.8 (2)
O4—Fe—O2—N1	−92.72 (12)	N3—C8—C9—C10	−29.2 (3)
O5—Fe—O2—N1	96.80 (12)	O3—C8—C9—C14	−27.4 (3)
O1—Fe—O2—N1	9.49 (11)	N3—C8—C9—C14	153.54 (19)
O3—Fe—O2—N1	−36.0 (3)	C14—C9—C10—C11	−1.0 (3)
Fe—O2—N1—C1	−11.7 (2)	C8—C9—C10—C11	−178.25 (19)
O2—N1—C1—O1	6.1 (3)	C9—C10—C11—C12	−1.7 (3)
O2—N1—C1—C2	−174.36 (16)	C10—C11—C12—N4	−177.0 (2)
N1—C1—O1—Fe	2.5 (2)	C10—C11—C12—C13	2.9 (3)
C2—C1—O1—Fe	−176.99 (14)	N4—C12—C13—C14	178.27 (19)
O2—Fe—O1—C1	−6.88 (13)	C11—C12—C13—C14	−1.6 (3)
O6—Fe—O1—C1	−62.3 (2)	C12—C13—C14—C9	−1.0 (3)
O4—Fe—O1—C1	83.59 (13)	C10—C9—C14—C13	2.3 (3)
O5—Fe—O1—C1	−111.26 (13)	C8—C9—C14—C13	179.61 (18)
O3—Fe—O1—C1	161.76 (13)	O2—Fe—O6—N5	−100.53 (12)
O1—C1—C2—C3	20.6 (3)	O4—Fe—O6—N5	166.72 (12)
N1—C1—C2—C3	−158.8 (2)	O5—Fe—O6—N5	3.73 (11)
O1—C1—C2—C7	−160.5 (2)	O1—Fe—O6—N5	−46.5 (3)
N1—C1—C2—C7	20.0 (3)	O3—Fe—O6—N5	88.00 (12)
C7—C2—C3—C4	−1.3 (3)	Fe—O6—N5—C15	−4.7 (2)
C1—C2—C3—C4	177.7 (2)	O6—N5—C15—O5	2.6 (3)
C2—C3—C4—C5	0.9 (4)	O6—N5—C15—C16	−175.01 (16)
C3—C4—C5—N2	178.1 (2)	N5—C15—O5—Fe	0.8 (2)
C3—C4—C5—C6	0.6 (4)	C16—C15—O5—Fe	178.37 (13)
N2—C5—C6—C7	−179.2 (2)	O2—Fe—O5—C15	85.37 (13)
C4—C5—C6—C7	−1.7 (4)	O6—Fe—O5—C15	−2.56 (12)
C5—C6—C7—C2	1.3 (4)	O4—Fe—O5—C15	−64.7 (2)
C3—C2—C7—C6	0.2 (4)	O1—Fe—O5—C15	164.44 (12)
C1—C2—C7—C6	−178.7 (2)	O3—Fe—O5—C15	−106.35 (12)
O2—Fe—O4—N3	166.76 (12)	O5—C15—C16—C17	18.8 (3)
O6—Fe—O4—N3	−102.43 (12)	N5—C15—C16—C17	−163.68 (18)
O5—Fe—O4—N3	−42.2 (2)	O5—C15—C16—C21	−157.92 (18)
O1—Fe—O4—N3	87.02 (12)	N5—C15—C16—C21	19.6 (3)
O3—Fe—O4—N3	0.40 (11)	C21—C16—C17—C18	1.2 (3)
Fe—O4—N3—C8	1.7 (2)	C15—C16—C17—C18	−175.66 (18)
O4—N3—C8—O3	−4.0 (3)	C16—C17—C18—C19	0.4 (3)
O4—N3—C8—C9	175.04 (16)	C17—C18—C19—N6	179.44 (18)
N3—C8—O3—Fe	4.1 (2)	C17—C18—C19—C20	−2.4 (3)
C9—C8—O3—Fe	−174.89 (14)	N6—C19—C20—C21	−178.92 (19)
O2—Fe—O3—C8	−60.9 (3)	C18—C19—C20—C21	3.0 (3)
O6—Fe—O3—C8	86.72 (13)	C19—C20—C21—C16	−1.4 (3)
O4—Fe—O3—C8	−2.41 (12)	C17—C16—C21—C20	−0.6 (3)
O5—Fe—O3—C8	164.62 (13)	C15—C16—C21—C20	176.07 (18)
O1—Fe—O3—C8	−105.33 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1O7···O6i	0.78 (3)	1.91 (3)	2.694 (2)	175 (3)
N6—H1N6···O3ii	0.84 (2)	2.15 (2)	2.968 (2)	163.9 (19)
N5—H1N5···O7	0.84 (2)	1.91 (2)	2.740 (2)	176 (2)
N3—H1N3···O4iii	0.86 (3)	1.98 (3)	2.755 (2)	150 (2)
N1—H1N1···O2iv	0.84 (3)	1.99 (3)	2.737 (2)	149 (2)

Table 1

Selected bond lengths (Å)

Fe—O2	1.9615 (14)
Fe—O6	1.9769 (14)
Fe—O4	1.9822 (14)
Fe—O5	2.0444 (14)
Fe—O1	2.0470 (14)
Fe—O3	2.0654 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H1O7⋯O6i	0.78 (3)	1.91 (3)	2.694 (2)	175 (3)
N6—H1N6⋯O3ii	0.84 (2)	2.15 (2)	2.968 (2)	163.9 (19)
N5—H1N5⋯O7	0.84 (2)	1.91 (2)	2.740 (2)	176 (2)
N3—H1N3⋯O4iii	0.86 (3)	1.98 (3)	2.755 (2)	150 (2)
N1—H1N1⋯O2iv	0.84 (3)	1.99 (3)	2.737 (2)	149 (2)

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