In the crystal structure of the title compound, [Fe(C
11H
13N
2O
3)
3]·1.5C
3H
7NO·2H
2O, 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 (CONHCH
3) 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.
Supporting information
CCDC reference: 293881
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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
top
Crystal data top
[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) Å3 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.176 | w = 1/[σ2(Fo2) + (0.0906P)2] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0061 (15) |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1Wi | 0.88 | 2.15 | 2.912 (3) | 144 |
N6—H6A···O2W | 0.88 | 2.11 | 2.988 (4) | 179 |
O1W—H1WA···O9ii | 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. |