Redetermination of fac-tris­(benzo­hydrox­am­ato)­iron(III) tri­hydrate

Due to its importance as a model for naturally occurring iron(III) siderophores such as desferriox­amine B, the crystal structure of the title compound, [Fe(C₇H₆NO₂)₃]·3H₂O, which was reported previously (R = 0.12, one of water mol­ecules disordered), has been redetermined (R = 0.041 without disorder). The complex has pseudo-octahedral geometry around the Fe^III atom, with Fe-O bond lengths ranging from 1.9689 (18) to 2.0585 (17) Å and O-Fe-O bond angles in the chelate rings of 78.01 (7), 78.83 (7) and 78.95 (7)°. There is extensive hydrogen bonding involving the water mol­ecules and the hydro­xamate ligands.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(I)

Crystal data

[Fe(C7H6NO2)3]·3H2O	Dx = 1.450 Mg m^−3
Mr = 518.28	Melting point: unknown K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.9459 (9) Å	Cell parameters from 2250 reflections
b = 13.1082 (9) Å	θ = 2.1–27.0°
c = 13.9889 (9) Å	µ = 0.69 mm^−1
β = 90.300 (2)°	T = 200 K
V = 2373.8 (3) Å^3	Needle, red
Z = 4	0.40 × 0.10 × 0.10 mm
F(000) = 1076

Data collection

SMART CCD diffractometer	5218 independent reflections
Radiation source: fine-focus sealed X-ray tube	2491 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
Detector resolution: 8.33 pixels mm^-1	θmax = 27.0°, θmin = 2.1°
φ and ω scans	h = −16→16
Absorption correction: empirical (using intensity measurements) (SADABS; Siemens, 1996)	k = −11→16
Tmin = 0.770, Tmax = 0.934	l = −17→17
18000 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 0.73	w = 1/[σ^2(Fo^2) + (0.0222P)^2] where P = (Fo^2 + 2Fc^2)/3
5218 reflections	(Δ/σ)max < 0.001
337 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Geometry. Specified hydrogen bonds (with e.s.d.'s except fixed and riding H)

D—H H···A D···A <(DHA)

0.89 (2) 1.84 (3) 2.725 (4) 178 (2) N11—H11···O1_$1 0.88 (3) 1.83 (3) 2.698 (4) 169 (3) N21—H21···O2 0.88 (3) 1.95 (3) 2.777 (3) 157 (2) N31—H31···O12_$2 0.79 (3) 2.08 (3) 2.857 (3) 168 (4) O1—H1A···O3 0.88 (3) 1.88 (3) 2.757 (3) 174 (3) O1—H1B···O11_$3 0.80 (4) 1.94 (4) 2.732 (3) 170 (5) O2—H2A···O3 0.89 (4) 2.70 (5) 2.833 (3) 89 (3) O2—H2B···O21_$3 0.74 (3) 2.26 (3) 2.983 (3) 165 (4) O3—H3A···O32_$4 0.88 (3) 1.97 (3) 2.797 (3) 156 (3) O3—H3B···O31_$3 0.88 (3) 2.66 (3) 3.535 (3) 174 (3) O3—H3B···N31_$3 ** No suitable H-bond found for C35···C21_$5 = 4.042 (4) A ** ** No suitable H-bond found for C35···C22_$5 = 3.926 (4) A ** ** No suitable H-bond found for C35···C23_$5 = 3.760 (5) A ** ** No suitable H-bond found for C35···C24_$5 = 3.718 (5) A ** ** No suitable H-bond found for C35···C25_$5 = 3.824 (5) A ** ** No suitable H-bond found for C35···C26_$5 = 3.983 (5) A **

# C—H···π(arene) type interaction

Mean plane data ex-SHELXL97 for molecule (I) ############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

-9.9611(0.0103)x + 7.3496(0.0138)y - 4.2232(0.0169)z = 6.7403(0.0040)

* 0.0055 (0.0020) C11 * -0.0076 (0.0021) C12 * 0.0035 (0.0022) C13 * 0.0028 (0.0024) C14 * -0.0049 (0.0023) C15 * 0.0007 (0.0021) C16 - 0.3380 (0.0070) Fe1

Rms deviation of fitted atoms = 0.0047

2.2416(0.0155)x + 9.4557(0.0110)y - 9.3930(0.0128)z = 4.7872(0.0017)

Angle to previous plane (with approximate e.s.d.) = 61.55 (10)

* 0.0023 (0.0021) C21 * 0.0020 (0.0021) C22 * -0.0049 (0.0023) C23 * 0.0036 (0.0024) C24 * 0.0007 (0.0024) C25 * -0.0036 (0.0022) C26 0.3160 (0.0066) Fe1

Rms deviation of fitted atoms = 0.0032

-12.0831(0.0056)x + 0.7292(0.0175)y + 5.0291(0.0154)z = 2.2283(0.0141)

Angle to previous plane (with approximate e.s.d.) = 68.94 (10)

* 0.0017 (0.0020) C31 * -0.0049 (0.0022) C32 * 0.0036 (0.0023) C33 * 0.0011 (0.0023) C34 * -0.0044 (0.0022) C35 * 0.0030 (0.0021) C36 0.2265 (0.0067) Fe1

Rms deviation of fitted atoms = 0.0034

-9.9611(0.0103)x + 7.3496(0.0138)y - 4.2232(0.0169)z = 6.7403(0.0040)

Angle to previous plane (with approximate e.s.d.) = 50.14 (9)

* 0.0055 (0.0020) C11 * -0.0076 (0.0021) C12 * 0.0035 (0.0022) C13 * 0.0028 (0.0024) C14 * -0.0049 (0.0023) C15 * 0.0007 (0.0021) C16 - 0.3380 (0.0070) Fe1

Rms deviation of fitted atoms = 0.0047

-9.9611(0.0103)x + 7.3496(0.0138)y - 4.2232(0.0169)z = 6.7403(0.0040)

Angle to previous plane (with approximate e.s.d.) = 0.0 (2)

* 0.0055 (0.0020) C11 * -0.0076 (0.0021) C12 * 0.0035 (0.0022) C13 * 0.0028 (0.0024) C14 * -0.0049 (0.0023) C15 * 0.0007 (0.0021) C16 - 0.3380 (0.0070) Fe1

Rms deviation of fitted atoms = 0.0047

-6.3433(0.0207)x + 3.0548(0.0150)y - 11.7146(0.0113)z = 5.1119(0.0052)

Angle to previous plane (with approximate e.s.d.) = 40.12 (14)

* -0.0011 (0.0015) C1 * 0.0011 (0.0015) N11 * -0.0005 (0.0007) O11 * 0.0006 (0.0008) O12

Rms deviation of fitted atoms = 0.0009

2.2416(0.0155)x + 9.4557(0.0110)y - 9.3930(0.0128)z = 4.7872(0.0017)

Angle to previous plane (with approximate e.s.d.) = 49.72 (10)

* 0.0023 (0.0021) C21 * 0.0020 (0.0021) C22 * -0.0049 (0.0023) C23 * 0.0036 (0.0024) C24 * 0.0007 (0.0024) C25 * -0.0036 (0.0022) C26 0.3160 (0.0066) Fe1

Rms deviation of fitted atoms = 0.0032

3.7841(0.0241)x + 11.3038(0.0086)y - 5.8047(0.0132)z = 4.5716(0.0059)

Angle to previous plane (with approximate e.s.d.) = 18.21 (14)

* -0.0100 (0.0015) C2 * 0.0096 (0.0015) N21 * -0.0049 (0.0008) O21 * 0.0052 (0.0008) O22

Rms deviation of fitted atoms = 0.0078

-12.0831(0.0056)x + 0.7292(0.0175)y + 5.0291(0.0154)z = 2.2283(0.0141)

Angle to previous plane (with approximate e.s.d.) = 68.19 (13)

* 0.0017 (0.0020) C31 * -0.0049 (0.0022) C32 * 0.0036 (0.0023) C33 * 0.0011 (0.0023) C34 * -0.0044 (0.0022) C35 * 0.0030 (0.0021) C36 0.2265 (0.0067) Fe1

Rms deviation of fitted atoms = 0.0034

-11.7164(0.0062)x + 2.5320(0.0191)y + 5.3676(0.0203)z = 2.9633(0.0153)

Angle to previous plane (with approximate e.s.d.) = 8.17 (12)

* -0.0071 (0.0016) C3 * 0.0069 (0.0015) N31 * -0.0035 (0.0008) O31 * 0.0037 (0.0008) O32

Rms deviation of fitted atoms = 0.0056

-9.9611(0.0103)x + 7.3496(0.0138)y - 4.2232(0.0169)z = 6.7403(0.0040)

Angle to previous plane (with approximate e.s.d.) = 46.47 (10)

* 0.0055 (0.0020) C11 * -0.0076 (0.0021) C12 * 0.0035 (0.0022) C13 * 0.0028 (0.0024) C14 * -0.0049 (0.0023) C15 * 0.0007 (0.0021) C16 - 0.3380 (0.0070) Fe1

Rms deviation of fitted atoms = 0.0047

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	−0.25900 (3)	0.40892 (3)	−0.19345 (3)	0.02924 (12)
O11	−0.38044 (15)	0.44307 (14)	−0.11478 (13)	0.0351 (5)
O12	−0.33371 (14)	0.27069 (13)	−0.18513 (12)	0.0313 (5)
O21	−0.15576 (14)	0.41026 (15)	−0.08935 (12)	0.0337 (5)
O22	−0.14393 (14)	0.32378 (14)	−0.25179 (13)	0.0334 (5)
O31	−0.23216 (15)	0.55460 (13)	−0.21696 (12)	0.0335 (5)
O32	−0.31330 (14)	0.42429 (14)	−0.33127 (12)	0.0326 (5)
N11	−0.4450 (2)	0.3620 (2)	−0.10111 (17)	0.0346 (6)
N21	−0.0645 (2)	0.36664 (18)	−0.11733 (18)	0.0333 (6)
N31	−0.26717 (18)	0.5841 (2)	−0.30532 (16)	0.0318 (6)
C1	−0.4182 (2)	0.2742 (2)	−0.13834 (18)	0.0265 (7)
C11	−0.4864 (2)	0.1850 (2)	−0.1281 (2)	0.0324 (7)
C12	−0.4996 (2)	0.1206 (2)	−0.2059 (2)	0.0401 (8)
C13	−0.5652 (2)	0.0379 (3)	−0.1977 (3)	0.0504 (10)
C14	−0.6151 (3)	0.0183 (3)	−0.1141 (3)	0.0578 (10)
C15	−0.6013 (2)	0.0806 (3)	−0.0363 (2)	0.0517 (9)
C16	−0.5373 (2)	0.1640 (2)	−0.0434 (2)	0.0413 (8)
C2	−0.0624 (2)	0.3212 (2)	−0.2010 (2)	0.0303 (7)
C21	0.0309 (2)	0.2669 (2)	−0.2339 (2)	0.0332 (7)
C22	0.0191 (2)	0.1968 (2)	−0.3072 (2)	0.0417 (8)
C23	0.1021 (3)	0.1428 (3)	−0.3410 (2)	0.0538 (10)
C24	0.1991 (3)	0.1584 (3)	−0.3031 (3)	0.0599 (11)
C25	0.2119 (3)	0.2279 (3)	−0.2297 (3)	0.0566 (10)
C26	0.1289 (2)	0.2819 (2)	−0.1948 (2)	0.0449 (9)
C3	−0.3067 (2)	0.5161 (2)	−0.36226 (19)	0.0272 (7)
C31	−0.3428 (2)	0.5450 (2)	−0.45915 (19)	0.0289 (7)
C32	−0.3480 (2)	0.6458 (2)	−0.4876 (2)	0.0394 (8)
C33	−0.3848 (3)	0.6700 (3)	−0.5779 (2)	0.0534 (10)
C34	−0.4149 (2)	0.5935 (3)	−0.6396 (2)	0.0506 (9)
C35	−0.4088 (2)	0.4937 (3)	−0.6116 (2)	0.0438 (9)
C36	−0.3736 (2)	0.4691 (2)	−0.5220 (2)	0.0364 (8)
O1	0.36854 (18)	0.40503 (19)	−0.02120 (16)	0.0504 (6)
O2	0.0724 (2)	0.4019 (2)	0.0249 (2)	0.0743 (9)
O3	0.2309 (2)	0.28186 (17)	0.08850 (16)	0.0444 (7)
H11	−0.506 (2)	0.3746 (19)	−0.0746 (16)	0.027 (8)*
H21	−0.014 (2)	0.375 (2)	−0.076 (2)	0.053 (11)*
H31	−0.244 (2)	0.644 (2)	−0.3242 (18)	0.040 (9)*
H1A	0.330 (3)	0.366 (3)	0.002 (2)	0.076*
H1B	0.370 (3)	0.451 (3)	0.025 (2)	0.076*
H2A	0.114 (3)	0.364 (3)	0.048 (3)	0.112*
H2B	0.119 (3)	0.422 (4)	−0.018 (3)	0.112*
H3A	0.229 (3)	0.228 (3)	0.102 (3)	0.067*
H3B	0.237 (3)	0.319 (2)	0.140 (2)	0.067*
H12	−0.4641	0.1332	−0.2639	0.048*
H13	−0.5757	−0.0058	−0.2511	0.060*
H14	−0.6597	−0.0391	−0.1097	0.069*
H15	−0.6357	0.0663	0.0221	0.062*
H16	−0.5279	0.2076	0.0102	0.050*
H22	−0.0473	0.1860	−0.3344	0.050*
H23	0.0924	0.0945	−0.3908	0.065*
H24	0.2566	0.1217	−0.3271	0.072*
H25	0.2787	0.2386	−0.2031	0.068*
H26	0.1386	0.3292	−0.1441	0.054*
H32	−0.3263	0.6985	−0.4453	0.047*
H33	−0.3893	0.7393	−0.5974	0.064*
H34	−0.4399	0.6101	−0.7017	0.061*
H35	−0.4291	0.4412	−0.6546	0.053*
H36	−0.3704	0.3996	−0.5029	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0307 (2)	0.0214 (2)	0.0356 (2)	−0.0006 (2)	−0.00118 (18)	−0.0010 (2)
O11	0.0351 (12)	0.0202 (12)	0.0502 (13)	−0.0083 (10)	0.0086 (10)	−0.0043 (9)
O12	0.0319 (12)	0.0189 (12)	0.0431 (12)	0.0017 (9)	0.0043 (10)	−0.0007 (9)
O21	0.0338 (12)	0.0312 (12)	0.0361 (11)	0.0073 (11)	−0.0003 (9)	−0.0032 (10)
O22	0.0293 (12)	0.0352 (13)	0.0357 (11)	0.0021 (10)	−0.0068 (10)	−0.0053 (9)
O31	0.0452 (13)	0.0267 (12)	0.0285 (12)	−0.0070 (9)	−0.0090 (10)	0.0014 (8)
O32	0.0390 (12)	0.0183 (12)	0.0405 (11)	−0.0023 (10)	−0.0084 (9)	−0.0012 (9)
N11	0.0310 (16)	0.0309 (17)	0.0418 (16)	−0.0007 (14)	0.0067 (13)	−0.0058 (13)
N21	0.0339 (17)	0.0286 (16)	0.0374 (16)	0.0004 (13)	−0.0078 (14)	−0.0002 (12)
N31	0.0441 (17)	0.0190 (15)	0.0324 (14)	−0.0073 (14)	−0.0028 (12)	0.0011 (13)
C1	0.0299 (18)	0.0206 (18)	0.0291 (16)	0.0041 (14)	−0.0013 (14)	−0.0002 (13)
C11	0.0287 (18)	0.0195 (18)	0.0491 (19)	0.0050 (15)	0.0019 (15)	0.0005 (15)
C12	0.0313 (19)	0.033 (2)	0.056 (2)	0.0015 (16)	−0.0001 (16)	−0.0095 (16)
C13	0.038 (2)	0.031 (2)	0.082 (3)	0.0010 (17)	−0.003 (2)	−0.0232 (19)
C14	0.042 (2)	0.028 (2)	0.103 (3)	−0.0096 (18)	0.008 (2)	−0.001 (2)
C15	0.042 (2)	0.040 (2)	0.074 (2)	−0.0061 (19)	0.0116 (18)	0.015 (2)
C16	0.040 (2)	0.032 (2)	0.052 (2)	−0.0044 (16)	0.0076 (17)	−0.0009 (16)
C2	0.0343 (19)	0.0195 (18)	0.0371 (18)	−0.0044 (15)	−0.0028 (15)	0.0049 (14)
C21	0.0367 (19)	0.0232 (19)	0.0398 (18)	0.0026 (15)	0.0037 (15)	0.0085 (14)
C22	0.039 (2)	0.046 (2)	0.040 (2)	0.0123 (18)	−0.0017 (16)	0.0043 (16)
C23	0.061 (3)	0.056 (3)	0.044 (2)	0.022 (2)	0.002 (2)	0.0020 (17)
C24	0.052 (3)	0.060 (3)	0.069 (3)	0.026 (2)	0.016 (2)	0.009 (2)
C25	0.034 (2)	0.054 (3)	0.081 (3)	0.006 (2)	0.002 (2)	0.014 (2)
C26	0.035 (2)	0.041 (2)	0.058 (2)	0.0039 (17)	−0.0022 (17)	0.0000 (17)
C3	0.0257 (17)	0.0218 (18)	0.0340 (17)	0.0009 (14)	−0.0004 (14)	−0.0043 (14)
C31	0.0261 (17)	0.0276 (19)	0.0330 (17)	0.0010 (14)	0.0031 (14)	0.0010 (14)
C32	0.049 (2)	0.029 (2)	0.0402 (19)	−0.0001 (17)	−0.0030 (16)	−0.0026 (15)
C33	0.066 (3)	0.043 (2)	0.051 (2)	0.001 (2)	−0.008 (2)	0.0144 (19)
C34	0.055 (2)	0.063 (3)	0.0335 (18)	−0.004 (2)	−0.0073 (16)	0.008 (2)
C35	0.047 (2)	0.047 (2)	0.0369 (19)	0.0019 (18)	−0.0038 (16)	−0.0099 (16)
C36	0.0388 (19)	0.032 (2)	0.0388 (19)	0.0027 (16)	0.0014 (15)	−0.0064 (15)
O1	0.0532 (16)	0.0373 (16)	0.0608 (16)	−0.0069 (13)	0.0221 (12)	−0.0124 (12)
O2	0.074 (2)	0.057 (2)	0.092 (2)	0.0168 (17)	−0.0498 (16)	−0.0153 (18)
O3	0.0645 (16)	0.0302 (15)	0.0384 (13)	0.0026 (14)	−0.0046 (12)	0.0008 (11)

Geometric parameters (Å, º)

Fe1—O11	1.9753 (19)	C15—C16	1.376 (4)
Fe1—O21	1.9715 (18)	C21—C22	1.384 (4)
Fe1—O31	1.9689 (18)	C21—C26	1.394 (4)
Fe1—O12	2.0577 (18)	C22—C23	1.372 (4)
Fe1—O22	2.0356 (18)	C23—C24	1.376 (4)
Fe1—O32	2.0585 (17)	C24—C25	1.382 (4)
O11—N11	1.366 (3)	C25—C26	1.378 (4)
O21—N21	1.371 (3)	C31—C32	1.381 (4)
O31—N31	1.370 (3)	C31—C36	1.387 (4)
O12—C1	1.278 (3)	C32—C33	1.385 (4)
O22—C2	1.269 (3)	C33—C34	1.378 (4)
O32—C3	1.282 (3)	C34—C35	1.367 (4)
N11—C1	1.311 (3)	C35—C36	1.370 (4)
N21—C2	1.314 (3)	N11—H11	0.89 (2)
N31—C3	1.299 (3)	N21—H21	0.88 (3)
C1—C11	1.473 (4)	N31—H31	0.88 (3)
C2—C21	1.477 (4)	O1—H1A	0.79 (3)
C3—C31	1.481 (4)	O1—H1B	0.88 (3)
C11—C12	1.386 (4)	O2—H2A	0.80 (4)
C11—C16	1.387 (4)	O2—H2B	0.89 (4)
C12—C13	1.382 (4)	O3—H3A	0.74 (3)
C13—C14	1.364 (4)	O3—H3B	0.88 (3)
C14—C15	1.372 (4)
O11—Fe1—O12	78.01 (7)	C12—C11—C16	119.5 (3)
O21—Fe1—O22	78.83 (7)	C12—C11—C1	118.6 (3)
O31—Fe1—O32	78.95 (7)	C16—C11—C1	121.9 (3)
O11—Fe1—O21	97.17 (8)	C13—C12—C11	119.1 (3)
O11—Fe1—O31	90.86 (8)	C14—C13—C12	120.8 (3)
O21—Fe1—O31	89.72 (8)	C13—C14—C15	120.5 (3)
O11—Fe1—O22	159.05 (8)	C14—C15—C16	119.4 (3)
O12—Fe1—O31	161.26 (8)	C15—C16—C11	120.5 (3)
O21—Fe1—O32	156.61 (7)	O22—C2—N21	117.7 (3)
O21—Fe1—O12	106.44 (8)	O22—C2—C21	121.2 (3)
O22—Fe1—O12	83.40 (7)	N21—C2—C21	121.1 (3)
O11—Fe1—O32	103.34 (8)	C22—C21—C26	118.7 (3)
O12—Fe1—O32	88.90 (7)	C22—C21—C2	117.6 (3)
O22—Fe1—O32	85.71 (7)	C26—C21—C2	123.7 (3)
O31—Fe1—O22	109.55 (8)	C23—C22—C21	120.9 (3)
N11—O11—Fe1	113.02 (15)	C22—C23—C24	120.4 (3)
C1—O12—Fe1	113.65 (17)	C23—C24—C25	119.3 (3)
N21—O21—Fe1	111.53 (15)	C26—C25—C24	120.7 (3)
C2—O22—Fe1	113.47 (17)	C25—C26—C21	119.9 (3)
N31—O31—Fe1	111.48 (15)	O32—C3—N31	117.6 (3)
C3—O32—Fe1	112.69 (16)	O32—C3—C31	122.0 (2)
C1—N11—O11	117.7 (2)	N31—C3—C31	120.4 (3)
C1—N11—H11	124.5 (17)	C32—C31—C36	119.4 (3)
O11—N11—H11	117.3 (17)	C32—C31—C3	121.6 (3)
C2—N21—O21	117.7 (3)	C36—C31—C3	119.0 (3)
C2—N21—H21	128.4 (19)	C31—C32—C33	119.8 (3)
O21—N21—H21	113.8 (19)	C34—C33—C32	120.0 (3)
C3—N31—O31	119.2 (3)	C35—C34—C33	120.1 (3)
C3—N31—H31	124.1 (18)	C34—C35—C36	120.4 (3)
O31—N31—H31	114.1 (17)	C35—C36—C31	120.3 (3)
O12—C1—N11	117.6 (3)	H1A—O1—H1B	99 (3)
O12—C1—C11	122.4 (3)	H2A—O2—H2B	90 (4)
N11—C1—C11	119.9 (3)	H3A—O3—H3B	109 (3)
O31—Fe1—O11—N11	163.14 (17)	C16—C11—C12—C13	1.4 (4)
O21—Fe1—O11—N11	−107.03 (17)	C1—C11—C12—C13	−178.6 (3)
O22—Fe1—O11—N11	−29.6 (3)	C11—C12—C13—C14	−1.2 (5)
O12—Fe1—O11—N11	−1.67 (16)	C12—C13—C14—C15	0.2 (5)
O32—Fe1—O11—N11	84.29 (17)	C13—C14—C15—C16	0.6 (5)
O31—Fe1—O12—C1	−53.1 (3)	C14—C15—C16—C11	−0.4 (5)
O21—Fe1—O12—C1	95.64 (18)	C12—C11—C16—C15	−0.6 (4)
O11—Fe1—O12—C1	1.60 (17)	C1—C11—C16—C15	179.4 (3)
O22—Fe1—O12—C1	171.90 (18)	Fe1—O22—C2—N21	4.2 (3)
O32—Fe1—O12—C1	−102.29 (18)	Fe1—O22—C2—C21	−177.29 (19)
O31—Fe1—O21—N21	−102.77 (16)	O21—N21—C2—O22	2.4 (4)
O11—Fe1—O21—N21	166.40 (16)	O21—N21—C2—C21	−176.2 (2)
O22—Fe1—O21—N21	7.23 (16)	O22—C2—C21—C22	−17.2 (4)
O12—Fe1—O21—N21	86.84 (16)	N21—C2—C21—C22	161.3 (3)
O32—Fe1—O21—N21	−42.4 (3)	O22—C2—C21—C26	163.3 (3)
O31—Fe1—O22—C2	79.26 (19)	N21—C2—C21—C26	−18.2 (4)
O21—Fe1—O22—C2	−6.42 (18)	C26—C21—C22—C23	0.0 (4)
O11—Fe1—O22—C2	−87.2 (3)	C2—C21—C22—C23	−179.5 (3)
O12—Fe1—O22—C2	−114.68 (19)	C21—C22—C23—C24	−0.7 (5)
O32—Fe1—O22—C2	155.93 (19)	C22—C23—C24—C25	0.9 (5)
O21—Fe1—O31—N31	162.12 (16)	C23—C24—C25—C26	−0.3 (5)
O11—Fe1—O31—N31	−100.71 (16)	C24—C25—C26—C21	−0.4 (5)
O22—Fe1—O31—N31	84.08 (16)	C22—C21—C26—C25	0.5 (4)
O12—Fe1—O31—N31	−47.8 (3)	C2—C21—C26—C25	180.0 (3)
O32—Fe1—O31—N31	2.72 (15)	Fe1—O32—C3—N31	0.8 (3)
O31—Fe1—O32—C3	−2.01 (18)	Fe1—O32—C3—C31	−179.08 (19)
O21—Fe1—O32—C3	−64.4 (3)	O31—N31—C3—O32	1.7 (4)
O11—Fe1—O32—C3	86.24 (19)	O31—N31—C3—C31	−178.4 (2)
O22—Fe1—O32—C3	−112.90 (18)	O32—C3—C31—C32	171.4 (3)
O12—Fe1—O32—C3	163.64 (18)	N31—C3—C31—C32	−8.4 (4)
Fe1—O11—N11—C1	1.7 (3)	O32—C3—C31—C36	−7.4 (4)
Fe1—O21—N21—C2	−7.7 (3)	N31—C3—C31—C36	172.7 (3)
Fe1—O31—N31—C3	−3.4 (3)	C36—C31—C32—C33	0.7 (4)
Fe1—O12—C1—N11	−1.2 (3)	C3—C31—C32—C33	−178.2 (3)
Fe1—O12—C1—C11	176.7 (2)	C31—C32—C33—C34	−0.8 (5)
O11—N11—C1—O12	−0.3 (4)	C32—C33—C34—C35	0.3 (5)
O11—N11—C1—C11	−178.2 (2)	C33—C34—C35—C36	0.5 (5)
O12—C1—C11—C12	−38.7 (4)	C34—C35—C36—C31	−0.7 (5)
N11—C1—C11—C12	139.1 (3)	C32—C31—C36—C35	0.1 (4)
O12—C1—C11—C16	141.3 (3)	C3—C31—C36—C35	179.0 (3)
N11—C1—C11—C16	−40.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1^i	0.89 (2)	1.84 (3)	2.725 (4)	178 (2)
N21—H21···O2	0.88 (3)	1.83 (3)	2.698 (4)	169 (3)
N31—H31···O12^ii	0.88 (3)	1.95 (3)	2.777 (3)	157 (2)
O1—H1A···O3	0.79 (3)	2.08 (3)	2.857 (3)	168 (4)
O1—H1B···O11^iii	0.88 (3)	1.88 (3)	2.757 (3)	174 (3)
O2—H2A···O3	0.80 (4)	1.94 (4)	2.732 (3)	170 (5)
O2—H2B···O21^iii	0.89 (4)	2.70 (5)	2.833 (3)	89 (3)
O3—H3A···O32^iv	0.74 (3)	2.26 (3)	2.983 (3)	165 (4)
O3—H3B···O31^iii	0.88 (3)	1.97 (3)	2.797 (3)	156 (3)
O3—H3B···N31^iii	0.88 (3)	2.66 (3)	3.535 (3)	174 (3)

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