Tris(1-cyclo­propyl-6-methyl-2-(N-methyl­amino­carbonyl)-4-oxo-1,4-dihydro­pyridin-4-olato)iron(III) dimethyl­formamide sesquisolvate dihydrate

In the crystal structure of the title compound, [Fe(C₁₁H₁₃N₂O₃)₃]·1.5C₃H₇NO·2H₂O, the Fe^III ion is six-coordinated in a distorted octa­hedral configuration consisting of six donor O atoms from three bidentate ligands. The Fe complex crystallizes with two mol­ecules of water and one and a half mol­ecules of dimethyl­formamide (DMF). The three amino­carb­oxy groups (CONHCH₃) are all rotated out of the planes of their respective pyridinone rings. Inter­molecular O—H...O and N—H...O hydrogen bonds contribute to the stabilization of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
Some non-H atoms missing
• R factor = 0.062
• wR factor = 0.176
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of .     259.00 A   3  

Author Response: See experimental text

Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O2W    -   H2WA   ...          ?

Author Response: See experimental text

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.805     0.949
            Tmin(prime) and Tmax expected:      0.909     0.959
            RR(prime) =      0.894
            Please check that your absorption correction is appropriate.
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    2
           From the CIF: _chemical_formula_weight           865.23
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   36.00  432.40
           H         1.01   50.00   50.40
           O        16.00   12.00  191.99
           N        14.01    7.00   98.05
           Fe       55.85    1.00   55.85
           Calculated formula weight              828.68
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     865.23
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.97
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   O5      ..       5.89 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   O6      ..       5.18 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        N1S
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C2S
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         11
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C37.5 H53.5 Fe1 N7.5 O12.5
            Atom count from the _atom_site data:  C36 H50 Fe1 N7 O12
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C37.50 H53.50 Fe N7.50 O12.50
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         75.00     72.00    3.00
           H        107.00    100.00    7.00
           Fe         2.00      2.00    0.00
           N         15.00     14.00    1.00
           O         25.00     24.00    1.00

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  17 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

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

---

Computing details

Data collection: COLLECT (Nonius, 2003); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Tris(1-cyclopropyl-6-methyl-2-N-methylaminocarbonyl-4-oxo-1,4-dihydropyridin- 4-olato)iron(III) dimethylformamide sesquisolvate dihydrate

Crystal data

[Fe(C11H13N2O3)3]·1.5C3H7NO·2H2O	Z = 2
Mr = 865.23	F(000) = 914
Triclinic, P1	Dx = 1.342 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.9319 (8) Å	Cell parameters from 20782 reflections
b = 14.3968 (9) Å	θ = 2.6–26.6°
c = 15.3024 (9) Å	µ = 0.42 mm^−1
α = 116.811 (3)°	T = 150 K
β = 108.353 (3)°	Plate, red
γ = 95.164 (4)°	0.22 × 0.21 × 0.10 mm
V = 2141.6 (2) Å^3

Data collection

Bruker–Nonius KappaCCD diffractometer	9756 independent reflections
Radiation source: fine-focus sealed tube	6632 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 9 pixels mm^-1	θmax = 27.6°, θmin = 2.6°
φ scans and ω scans with κ offsets	h = −15→14
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −18→18
Tmin = 0.805, Tmax = 0.949	l = −16→19
20782 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.176	w = 1/[σ^2(Fo^2) + (0.0906P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
9756 reflections	Δρmax = 1.46 e Å^−3
514 parameters	Δρmin = −0.49 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (15)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.40845 (3)	0.61905 (3)	0.24501 (3)	0.02577 (15)
O1	0.54528 (17)	0.74886 (14)	0.28787 (15)	0.0288 (4)
O2	0.42087 (17)	0.72787 (14)	0.39262 (15)	0.0311 (5)
O3	0.24981 (17)	0.53615 (14)	0.22785 (15)	0.0300 (4)
O4	0.28738 (17)	0.65936 (15)	0.15130 (15)	0.0305 (4)
O5	0.49899 (17)	0.53245 (15)	0.29499 (15)	0.0299 (4)
O6	0.43890 (17)	0.52544 (14)	0.11307 (15)	0.0286 (4)
O7	0.7221 (2)	1.06155 (16)	0.3855 (2)	0.0548 (7)
O8	−0.0669 (2)	0.36754 (16)	0.14819 (17)	0.0434 (6)
O9	0.74387 (19)	0.40050 (17)	0.38838 (17)	0.0402 (5)
N1	0.6925 (2)	1.00665 (18)	0.5379 (2)	0.0348 (6)
N2	−0.0548 (2)	0.57068 (17)	0.13463 (19)	0.0301 (5)
N3	0.6137 (2)	0.30917 (17)	0.15553 (19)	0.0296 (5)
N4	0.6964 (2)	0.88536 (19)	0.2732 (2)	0.0399 (6)
H4A	0.6831	0.8190	0.2618	0.048*
N5	0.0638 (2)	0.4903 (2)	0.3181 (2)	0.0363 (6)
H5A	0.1167	0.5548	0.3612	0.044*
N6	0.5512 (3)	0.3891 (2)	0.3828 (2)	0.0425 (7)
H6A	0.4734	0.3778	0.3446	0.051*
C1	0.5758 (2)	0.8306 (2)	0.3847 (2)	0.0274 (6)
C2	0.5075 (2)	0.8165 (2)	0.4428 (2)	0.0287 (6)
C3	0.5379 (3)	0.8992 (2)	0.5472 (2)	0.0336 (7)
H3A	0.4931	0.8916	0.5862	0.040*
C4	0.6320 (3)	0.9919 (2)	0.5950 (2)	0.0329 (7)
C5	0.6588 (3)	0.9302 (2)	0.4292 (2)	0.0310 (6)
C6	0.6674 (3)	1.0771 (3)	0.7090 (3)	0.0452 (8)
H6B	0.6795	1.1486	0.7157	0.068*
H6C	0.7439	1.0730	0.7540	0.068*
H6D	0.6021	1.0655	0.7319	0.068*
C7	0.7988 (3)	1.1008 (3)	0.5935 (3)	0.0518 (10)
H7A	0.7797	1.1710	0.6066	0.062*
C8	0.9082 (3)	1.1079 (3)	0.6783 (3)	0.0658 (12)
H8A	0.9063	1.0470	0.6920	0.079*
H8B	0.9540	1.1801	0.7422	0.079*
C9	0.9120 (3)	1.0876 (3)	0.5744 (3)	0.0655 (13)
H9A	0.9600	1.1472	0.5743	0.079*
H9B	0.9123	1.0141	0.5240	0.079*
C10	0.6971 (3)	0.9651 (2)	0.3627 (3)	0.0387 (8)
C11	0.7175 (4)	0.9052 (3)	0.1929 (3)	0.0550 (10)
H11A	0.6922	0.8364	0.1259	0.082*
H11B	0.8049	0.9394	0.2184	0.082*
H11C	0.6693	0.9531	0.1807	0.082*
C12	0.1551 (2)	0.5656 (2)	0.1869 (2)	0.0275 (6)
C13	0.1761 (2)	0.6297 (2)	0.1409 (2)	0.0267 (6)
C14	0.0764 (3)	0.6537 (2)	0.0862 (2)	0.0304 (6)
H14A	0.0875	0.6906	0.0500	0.036*
C15	−0.0387 (3)	0.6244 (2)	0.0839 (2)	0.0314 (7)
C16	0.0397 (2)	0.5367 (2)	0.1818 (2)	0.0286 (6)
C17	−0.1442 (3)	0.6532 (2)	0.0272 (3)	0.0393 (7)
H17A	−0.1274	0.6646	−0.0265	0.059*
H17B	−0.1549	0.7196	0.0788	0.059*
H17C	−0.2192	0.5941	−0.0081	0.059*
C18	−0.1729 (2)	0.5471 (2)	0.1411 (2)	0.0353 (7)
H18A	−0.2352	0.4788	0.0793	0.042*
C19	−0.1729 (3)	0.5777 (3)	0.2476 (3)	0.0431 (8)
H19A	−0.2323	0.5285	0.2514	0.052*
H19B	−0.0930	0.6142	0.3100	0.052*
C20	−0.2223 (3)	0.6387 (2)	0.1949 (3)	0.0446 (8)
H20A	−0.1730	0.7131	0.2243	0.054*
H20B	−0.3123	0.6273	0.1657	0.054*
C21	0.0075 (2)	0.4578 (2)	0.2158 (2)	0.0314 (6)
C22	0.0413 (3)	0.4232 (3)	0.3616 (3)	0.0491 (9)
H22A	0.0936	0.4608	0.4381	0.074*
H22B	0.0603	0.3547	0.3250	0.074*
H22C	−0.0451	0.4087	0.3512	0.074*
C23	0.5264 (2)	0.4566 (2)	0.2216 (2)	0.0264 (6)
C24	0.4943 (2)	0.4549 (2)	0.1220 (2)	0.0259 (6)
C25	0.5293 (3)	0.3812 (2)	0.0451 (2)	0.0283 (6)
H25A	0.5115	0.3805	−0.0203	0.034*
C26	0.5889 (3)	0.3097 (2)	0.0617 (2)	0.0300 (6)
C27	0.5853 (2)	0.3831 (2)	0.2357 (2)	0.0286 (6)
C28	0.6308 (3)	0.2346 (2)	−0.0197 (3)	0.0385 (7)
H28A	0.6217	0.2550	−0.0741	0.058*
H28B	0.5809	0.1602	−0.0536	0.058*
H28C	0.7172	0.2395	0.0153	0.058*
C29	0.6730 (3)	0.2298 (2)	0.1716 (3)	0.0386 (7)
H29A	0.7647	0.2503	0.1990	0.046*
C30	0.6105 (4)	0.1134 (3)	0.0958 (3)	0.0536 (9)
H30A	0.6621	0.0639	0.0759	0.064*
H30B	0.5294	0.0934	0.0382	0.064*
C31	0.6191 (4)	0.1647 (3)	0.2079 (3)	0.0549 (10)
H31A	0.5434	0.1765	0.2196	0.066*
H31B	0.6760	0.1470	0.2573	0.066*
C32	0.6328 (3)	0.3904 (2)	0.3421 (2)	0.0334 (7)
C33	0.5879 (4)	0.4064 (3)	0.4911 (3)	0.0594 (10)
H33A	0.5180	0.4139	0.5119	0.089*
H33B	0.6558	0.4723	0.5411	0.089*
H33C	0.6142	0.3444	0.4925	0.089*
N1S	0.8417 (3)	0.7797 (2)	0.5850 (3)	0.0636 (9)
O1S	0.8681 (6)	0.9060 (4)	0.7517 (4)	0.175 (3)
C1S	0.9597 (7)	0.8205 (5)	0.6041 (9)	0.194 (5)
H1SA	1.0060	0.8703	0.6809	0.291*
H1SB	0.9608	0.8594	0.5657	0.291*
H1SC	0.9974	0.7611	0.5795	0.291*
C2S	0.8019 (5)	0.8230 (4)	0.6642 (4)	0.0880 (15)
H2SA	0.7224	0.7900	0.6534	0.106*
C3S	0.7574 (6)	0.6885 (4)	0.4838 (4)	0.104 (2)
H3SA	0.6794	0.6694	0.4885	0.156*
H3SB	0.7924	0.6266	0.4663	0.156*
H3SC	0.7431	0.7074	0.4279	0.156*
O1W	0.8409 (2)	1.29071 (19)	0.4982 (2)	0.0565 (7)
H1WA	0.8077	1.3137	0.4576	0.085*
H1WB	0.7987	1.2258	0.4615	0.085*
O2W	0.2873 (2)	0.3484 (2)	0.2510 (2)	0.0647 (8)
H2WB	0.2845	0.4070	0.2522	0.097*
H2WA	0.2327	0.2914	0.2012	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0240 (2)	0.0269 (2)	0.0245 (2)	0.00513 (15)	0.00792 (16)	0.01315 (17)
O1	0.0295 (10)	0.0272 (9)	0.0260 (10)	0.0052 (8)	0.0110 (8)	0.0112 (8)
O2	0.0327 (10)	0.0304 (10)	0.0280 (11)	0.0037 (8)	0.0135 (9)	0.0131 (9)
O3	0.0251 (9)	0.0333 (10)	0.0315 (11)	0.0060 (8)	0.0101 (8)	0.0177 (9)
O4	0.0276 (10)	0.0340 (10)	0.0313 (11)	0.0075 (8)	0.0103 (8)	0.0188 (9)
O5	0.0321 (10)	0.0355 (10)	0.0226 (10)	0.0099 (8)	0.0119 (8)	0.0146 (8)
O6	0.0293 (10)	0.0284 (9)	0.0278 (10)	0.0074 (8)	0.0083 (8)	0.0162 (8)
O7	0.0741 (17)	0.0277 (11)	0.0680 (17)	0.0092 (11)	0.0426 (15)	0.0201 (11)
O8	0.0436 (12)	0.0356 (11)	0.0336 (12)	−0.0055 (10)	0.0059 (10)	0.0130 (10)
O9	0.0372 (12)	0.0541 (13)	0.0333 (12)	0.0166 (10)	0.0120 (10)	0.0260 (10)
N1	0.0294 (12)	0.0260 (12)	0.0348 (14)	0.0053 (10)	0.0112 (11)	0.0060 (10)
N2	0.0238 (11)	0.0277 (11)	0.0260 (12)	0.0033 (9)	0.0062 (10)	0.0069 (10)
N3	0.0323 (12)	0.0267 (11)	0.0297 (13)	0.0089 (10)	0.0121 (10)	0.0144 (10)
N4	0.0518 (16)	0.0276 (12)	0.0486 (16)	0.0099 (11)	0.0325 (14)	0.0178 (12)
N5	0.0323 (13)	0.0394 (13)	0.0293 (14)	0.0009 (11)	0.0091 (11)	0.0150 (11)
N6	0.0439 (15)	0.0608 (17)	0.0453 (17)	0.0259 (13)	0.0235 (13)	0.0385 (15)
C1	0.0268 (14)	0.0275 (13)	0.0255 (14)	0.0077 (11)	0.0092 (12)	0.0122 (12)
C2	0.0287 (14)	0.0295 (14)	0.0284 (15)	0.0097 (12)	0.0092 (12)	0.0162 (12)
C3	0.0367 (16)	0.0374 (15)	0.0297 (16)	0.0156 (13)	0.0167 (13)	0.0160 (13)
C4	0.0305 (15)	0.0299 (14)	0.0284 (15)	0.0114 (12)	0.0069 (12)	0.0097 (12)
C5	0.0268 (14)	0.0272 (14)	0.0339 (16)	0.0081 (11)	0.0129 (12)	0.0110 (12)
C6	0.0420 (18)	0.0419 (17)	0.0338 (18)	0.0156 (14)	0.0109 (15)	0.0072 (14)
C7	0.0360 (17)	0.0331 (16)	0.056 (2)	0.0007 (14)	0.0183 (16)	0.0001 (15)
C8	0.0342 (18)	0.059 (2)	0.049 (2)	0.0020 (16)	0.0037 (17)	−0.0048 (18)
C9	0.0403 (19)	0.051 (2)	0.061 (3)	−0.0018 (16)	0.0227 (18)	−0.0052 (18)
C10	0.0383 (17)	0.0276 (15)	0.050 (2)	0.0089 (13)	0.0235 (15)	0.0159 (14)
C11	0.074 (3)	0.0453 (19)	0.062 (2)	0.0118 (18)	0.043 (2)	0.0300 (18)
C12	0.0259 (14)	0.0265 (13)	0.0209 (14)	0.0064 (11)	0.0052 (11)	0.0077 (11)
C13	0.0260 (13)	0.0245 (13)	0.0202 (13)	0.0046 (11)	0.0056 (11)	0.0068 (11)
C14	0.0322 (15)	0.0261 (13)	0.0251 (15)	0.0059 (11)	0.0073 (12)	0.0101 (11)
C15	0.0292 (14)	0.0236 (13)	0.0247 (14)	0.0054 (11)	0.0037 (12)	0.0043 (11)
C16	0.0264 (14)	0.0263 (13)	0.0222 (14)	0.0036 (11)	0.0058 (11)	0.0071 (11)
C17	0.0301 (15)	0.0373 (16)	0.0357 (17)	0.0113 (13)	0.0031 (13)	0.0132 (14)
C18	0.0203 (13)	0.0351 (15)	0.0365 (17)	0.0026 (11)	0.0055 (12)	0.0120 (13)
C19	0.0290 (15)	0.0496 (18)	0.046 (2)	0.0072 (14)	0.0173 (14)	0.0195 (16)
C20	0.0302 (16)	0.0387 (17)	0.055 (2)	0.0110 (13)	0.0199 (15)	0.0145 (15)
C21	0.0266 (14)	0.0348 (15)	0.0270 (15)	0.0050 (12)	0.0095 (12)	0.0127 (13)
C22	0.052 (2)	0.058 (2)	0.0339 (18)	0.0004 (16)	0.0112 (15)	0.0270 (16)
C23	0.0228 (13)	0.0295 (13)	0.0239 (14)	0.0029 (11)	0.0080 (11)	0.0128 (11)
C24	0.0224 (13)	0.0254 (13)	0.0237 (14)	0.0002 (10)	0.0046 (11)	0.0119 (11)
C25	0.0325 (14)	0.0283 (13)	0.0202 (14)	0.0038 (11)	0.0082 (11)	0.0117 (11)
C26	0.0297 (14)	0.0298 (14)	0.0268 (15)	0.0037 (11)	0.0099 (12)	0.0132 (12)
C27	0.0276 (14)	0.0321 (14)	0.0277 (15)	0.0072 (11)	0.0108 (12)	0.0167 (12)
C28	0.0451 (18)	0.0374 (16)	0.0347 (17)	0.0159 (14)	0.0194 (14)	0.0165 (13)
C29	0.0423 (17)	0.0384 (16)	0.0407 (18)	0.0208 (14)	0.0175 (15)	0.0221 (14)
C30	0.070 (2)	0.0345 (17)	0.054 (2)	0.0184 (17)	0.0219 (19)	0.0214 (16)
C31	0.074 (3)	0.0457 (19)	0.062 (2)	0.0283 (18)	0.033 (2)	0.0346 (18)
C32	0.0385 (16)	0.0334 (15)	0.0348 (17)	0.0136 (13)	0.0155 (14)	0.0210 (13)
C33	0.071 (3)	0.093 (3)	0.057 (2)	0.046 (2)	0.040 (2)	0.058 (2)
N1S	0.077 (2)	0.0503 (18)	0.063 (2)	0.0188 (17)	0.0249 (19)	0.0299 (17)
O1S	0.215 (6)	0.121 (4)	0.081 (3)	0.046 (4)	0.018 (3)	−0.007 (3)
C1S	0.150 (7)	0.103 (5)	0.390 (15)	0.055 (5)	0.191 (9)	0.115 (7)
C2S	0.102 (4)	0.091 (3)	0.072 (3)	0.044 (3)	0.035 (3)	0.039 (3)
C3S	0.134 (5)	0.071 (3)	0.056 (3)	0.040 (3)	0.003 (3)	0.014 (2)
O1W	0.0557 (15)	0.0463 (13)	0.0546 (16)	0.0120 (11)	0.0067 (12)	0.0260 (12)
O2W	0.0536 (15)	0.0590 (15)	0.093 (2)	0.0148 (12)	0.0298 (15)	0.0478 (16)

Geometric parameters (Å, º)

Fe1—O5	1.972 (2)	C13—C14	1.395 (4)
Fe1—O3	2.0184 (18)	C14—C15	1.385 (4)
Fe1—O4	2.019 (2)	C14—H14A	0.9500
Fe1—O6	2.0298 (19)	C15—C17	1.496 (4)
Fe1—O2	2.0331 (19)	C16—C21	1.513 (4)
Fe1—O1	2.0637 (18)	C17—H17A	0.9800
O1—C1	1.313 (3)	C17—H17B	0.9800
O2—C2	1.291 (3)	C17—H17C	0.9800
O3—C12	1.315 (3)	C18—C19	1.485 (5)
O4—C13	1.293 (3)	C18—C20	1.493 (4)
O5—C23	1.323 (3)	C18—H18A	1.0000
O6—C24	1.295 (3)	C19—C20	1.485 (5)
O7—C10	1.251 (3)	C19—H19A	0.9900
O8—C21	1.244 (3)	C19—H19B	0.9900
O9—C32	1.249 (4)	C20—H20A	0.9900
N1—C4	1.367 (4)	C20—H20B	0.9900
N1—C5	1.410 (4)	C22—H22A	0.9800
N1—C7	1.463 (4)	C22—H22B	0.9800
N2—C15	1.358 (4)	C22—H22C	0.9800
N2—C16	1.392 (4)	C23—C27	1.381 (4)
N2—C18	1.464 (4)	C23—C24	1.437 (4)
N3—C26	1.375 (4)	C24—C25	1.395 (4)
N3—C27	1.380 (4)	C25—C26	1.372 (4)
N3—C29	1.468 (4)	C25—H25A	0.9500
N4—C10	1.329 (4)	C26—C28	1.499 (4)
N4—C11	1.467 (4)	C27—C32	1.495 (4)
N4—H4A	0.8800	C28—H28A	0.9800
N5—C21	1.319 (4)	C28—H28B	0.9800
N5—C22	1.447 (4)	C28—H28C	0.9800
N5—H5A	0.8800	C29—C31	1.478 (5)
N6—C32	1.314 (4)	C29—C30	1.479 (4)
N6—C33	1.466 (4)	C29—H29A	1.0000
N6—H6A	0.8800	C30—C31	1.493 (5)
C1—C5	1.392 (4)	C30—H30A	0.9900
C1—C2	1.443 (4)	C30—H30B	0.9900
C2—C3	1.394 (4)	C31—H31A	0.9900
C3—C4	1.381 (4)	C31—H31B	0.9900
C3—H3A	0.9500	C33—H33A	0.9800
C4—C6	1.496 (4)	C33—H33B	0.9800
C5—C10	1.485 (4)	C33—H33C	0.9800
C6—H6B	0.9800	N1S—C2S	1.348 (6)
C6—H6C	0.9800	N1S—C1S	1.360 (7)
C6—H6D	0.9800	N1S—C3S	1.443 (5)
C7—C8	1.479 (6)	O1S—C2S	1.251 (6)
C7—C9	1.480 (5)	C1S—H1SA	0.9800
C7—H7A	1.0000	C1S—H1SB	0.9800
C8—C9	1.497 (6)	C1S—H1SC	0.9800
C8—H8A	0.9900	C2S—H2SA	0.9500
C8—H8B	0.9900	C3S—H3SA	0.9800
C9—H9A	0.9900	C3S—H3SB	0.9800
C9—H9B	0.9900	C3S—H3SC	0.9800
C11—H11A	0.9800	O1W—H1WA	0.8400
C11—H11B	0.9800	O1W—H1WB	0.8400
C11—H11C	0.9800	O2W—H2WB	0.8400
C12—C16	1.370 (4)	O2W—H2WA	0.8400
C12—C13	1.436 (4)
O5—Fe1—O3	90.65 (8)	C15—C17—H17A	109.5
O5—Fe1—O4	161.25 (8)	C15—C17—H17B	109.5
O3—Fe1—O4	80.33 (8)	H17A—C17—H17B	109.5
O5—Fe1—O6	80.96 (8)	C15—C17—H17C	109.5
O3—Fe1—O6	106.44 (7)	H17A—C17—H17C	109.5
O4—Fe1—O6	85.85 (8)	H17B—C17—H17C	109.5
O5—Fe1—O2	93.94 (8)	N2—C18—C19	118.0 (2)
O3—Fe1—O2	85.82 (8)	N2—C18—C20	119.1 (2)
O4—Fe1—O2	101.69 (8)	C19—C18—C20	59.8 (2)
O6—Fe1—O2	166.67 (8)	N2—C18—H18A	116.1
O5—Fe1—O1	103.57 (8)	C19—C18—H18A	116.1
O3—Fe1—O1	159.40 (8)	C20—C18—H18A	116.1
O4—Fe1—O1	89.78 (8)	C20—C19—C18	60.4 (2)
O6—Fe1—O1	90.67 (7)	C20—C19—H19A	117.7
O2—Fe1—O1	78.50 (7)	C18—C19—H19A	117.7
C1—O1—Fe1	113.89 (17)	C20—C19—H19B	117.7
C2—O2—Fe1	115.01 (17)	C18—C19—H19B	117.7
C12—O3—Fe1	111.97 (17)	H19A—C19—H19B	114.9
C13—O4—Fe1	112.65 (17)	C19—C20—C18	59.8 (2)
C23—O5—Fe1	113.62 (17)	C19—C20—H20A	117.8
C24—O6—Fe1	112.61 (17)	C18—C20—H20A	117.8
C4—N1—C5	121.3 (2)	C19—C20—H20B	117.8
C4—N1—C7	118.6 (3)	C18—C20—H20B	117.8
C5—N1—C7	120.0 (3)	H20A—C20—H20B	114.9
C15—N2—C16	121.4 (2)	O8—C21—N5	123.9 (3)
C15—N2—C18	120.5 (2)	O8—C21—C16	119.9 (3)
C16—N2—C18	118.2 (2)	N5—C21—C16	116.2 (2)
C26—N3—C27	121.0 (2)	N5—C22—H22A	109.5
C26—N3—C29	119.7 (2)	N5—C22—H22B	109.5
C27—N3—C29	119.2 (2)	H22A—C22—H22B	109.5
C10—N4—C11	121.7 (3)	N5—C22—H22C	109.5
C10—N4—H4A	119.1	H22A—C22—H22C	109.5
C11—N4—H4A	119.1	H22B—C22—H22C	109.5
C21—N5—C22	122.0 (3)	O5—C23—C27	124.6 (3)
C21—N5—H5A	119.0	O5—C23—C24	116.1 (2)
C22—N5—H5A	119.0	C27—C23—C24	119.2 (2)
C32—N6—C33	121.0 (3)	O6—C24—C25	125.5 (3)
C32—N6—H6A	119.5	O6—C24—C23	116.5 (2)
C33—N6—H6A	119.5	C25—C24—C23	118.0 (3)
O1—C1—C5	124.8 (3)	C26—C25—C24	121.6 (3)
O1—C1—C2	115.5 (2)	C26—C25—H25A	119.2
C5—C1—C2	119.4 (2)	C24—C25—H25A	119.2
O2—C2—C3	124.8 (3)	C25—C26—N3	119.6 (2)
O2—C2—C1	116.8 (2)	C25—C26—C28	120.8 (3)
C3—C2—C1	118.3 (2)	N3—C26—C28	119.6 (3)
C4—C3—C2	121.2 (3)	N3—C27—C23	120.5 (3)
C4—C3—H3A	119.4	N3—C27—C32	118.4 (2)
C2—C3—H3A	119.4	C23—C27—C32	120.7 (2)
N1—C4—C3	120.0 (3)	C26—C28—H28A	109.5
N1—C4—C6	119.6 (3)	C26—C28—H28B	109.5
C3—C4—C6	120.4 (3)	H28A—C28—H28B	109.5
C1—C5—N1	118.6 (3)	C26—C28—H28C	109.5
C1—C5—C10	122.1 (3)	H28A—C28—H28C	109.5
N1—C5—C10	118.6 (2)	H28B—C28—H28C	109.5
C4—C6—H6B	109.5	N3—C29—C31	119.3 (3)
C4—C6—H6C	109.5	N3—C29—C30	118.5 (3)
H6B—C6—H6C	109.5	C31—C29—C30	60.6 (2)
C4—C6—H6D	109.5	N3—C29—H29A	115.7
H6B—C6—H6D	109.5	C31—C29—H29A	115.7
H6C—C6—H6D	109.5	C30—C29—H29A	115.7
N1—C7—C8	118.3 (4)	C29—C30—C31	59.7 (2)
N1—C7—C9	119.6 (3)	C29—C30—H30A	117.8
C8—C7—C9	60.8 (3)	C31—C30—H30A	117.8
N1—C7—H7A	115.7	C29—C30—H30B	117.8
C8—C7—H7A	115.7	C31—C30—H30B	117.8
C9—C7—H7A	115.7	H30A—C30—H30B	114.9
C7—C8—C9	59.6 (3)	C29—C31—C30	59.7 (2)
C7—C8—H8A	117.8	C29—C31—H31A	117.8
C9—C8—H8A	117.8	C30—C31—H31A	117.8
C7—C8—H8B	117.8	C29—C31—H31B	117.8
C9—C8—H8B	117.8	C30—C31—H31B	117.8
H8A—C8—H8B	114.9	H31A—C31—H31B	114.9
C7—C9—C8	59.6 (3)	O9—C32—N6	123.8 (3)
C7—C9—H9A	117.8	O9—C32—C27	120.7 (3)
C8—C9—H9A	117.8	N6—C32—C27	115.4 (3)
C7—C9—H9B	117.8	N6—C33—H33A	109.5
C8—C9—H9B	117.8	N6—C33—H33B	109.5
H9A—C9—H9B	115.0	H33A—C33—H33B	109.5
O7—C10—N4	121.7 (3)	N6—C33—H33C	109.5
O7—C10—C5	123.1 (3)	H33A—C33—H33C	109.5
N4—C10—C5	115.2 (2)	H33B—C33—H33C	109.5
N4—C11—H11A	109.5	C2S—N1S—C1S	119.4 (6)
N4—C11—H11B	109.5	C2S—N1S—C3S	117.9 (5)
H11A—C11—H11B	109.5	C1S—N1S—C3S	122.7 (6)
N4—C11—H11C	109.5	N1S—C1S—H1SA	109.5
H11A—C11—H11C	109.5	N1S—C1S—H1SB	109.5
H11B—C11—H11C	109.5	H1SA—C1S—H1SB	109.5
O3—C12—C16	125.1 (3)	N1S—C1S—H1SC	109.5
O3—C12—C13	116.0 (2)	H1SA—C1S—H1SC	109.5
C16—C12—C13	118.9 (3)	H1SB—C1S—H1SC	109.5
O4—C13—C14	124.2 (3)	O1S—C2S—N1S	120.9 (6)
O4—C13—C12	117.1 (2)	O1S—C2S—H2SA	119.5
C14—C13—C12	118.7 (2)	N1S—C2S—H2SA	119.5
C15—C14—C13	120.7 (3)	N1S—C3S—H3SA	109.5
C15—C14—H14A	119.7	N1S—C3S—H3SB	109.5
C13—C14—H14A	119.7	H3SA—C3S—H3SB	109.5
N2—C15—C14	119.6 (3)	N1S—C3S—H3SC	109.5
N2—C15—C17	120.4 (3)	H3SA—C3S—H3SC	109.5
C14—C15—C17	120.1 (3)	H3SB—C3S—H3SC	109.5
C12—C16—N2	120.4 (3)	H1WA—O1W—H1WB	100.2
C12—C16—C21	121.5 (3)	H2WB—O2W—H2WA	119.2
N2—C16—C21	117.8 (2)
N2—C16—C21—N5	−120.9 (3)	N1—C5—C10—N4	160.3 (3)
N3—C27—C32—N6	−131.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1	0.88	2.09	2.679 (3)	124
N5—H5A···O1W^i	0.88	2.15	2.912 (3)	144
N6—H6A···O2W	0.88	2.11	2.988 (4)	179
O1W—H1WA···O9^ii	0.84	2.03	2.857 (3)	168
O1W—H1WB···O7	0.84	2.06	2.890 (3)	170
O2W—H2WB···O3	0.84	2.11	2.936 (3)	170

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