Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021915/dn2152sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021915/dn2152Isup2.hkl |
CCDC reference: 288283
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.064
- wR factor = 0.202
- Data-to-parameter ratio = 21.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.91 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.32 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C31 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C35A PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C35A .. 2.94 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.50 Deg. C26A -C23 -C26B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 36.60 Deg. C24B -C23 -C24A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 38.10 Deg. C25A -C23 -C25B 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Bartos et al. (1995); Che et al. (1992); Collins et al. (1992); Liu et al. (2006); Marlin et al. (1999); Patra & Mukherjee (1999); Ray et al. (1993); Yan et al. (2006); Yang et al. (1991).
The ironIII complex [NEt4][Fe(bbpc)Cl2] was prepared according to the literature (Ray et al., 1993). Single crystals suitable for X-ray analysis were obtained by slow diffusion of ether into chloroform solution. Selected IR data (KBr, cm-1): 2968 (m), 1626 (amide I band, s), 1596 (amide II band, s), 1375 (s), 1171 (m), 957 (m), 853 (m). Anal calculated for C34H46Cl4N5O2Fe: C, 54.13; H, 6.15; N, 9.28. Found: C, 53.87; H, 6.36; N, 9.05. MS (FAB): 624 ([Fe(bbpc)Cl2]+).
All H atoms were fixed geometrically and treated as riding on their parent C atoms with C—H = 0.93 Å (aromatic), 0.97 Å (methylene) and 0.96Å (methyl) with Uiso(H) = 1.2Ueq(aromatic, methylene) or Uiso(H) = 1.5Ueq(methyl). One of the tertiobutyl group is disordered over two positions with occupancy in the ratio 0.39/0.61. This disorder was treated applying restraints to keep a reasonable chemical structure. The Cl atoms in the solvent molecule present large ellipsoids components but any attempts to modelize a reasonable model failed.
There has been a growing interest in the coordination chemistry of peptide complexes of iron in a +3 or higher oxidation state (Marlin et al., 1999; Che et al., 1992). Mascharak and Collins have provided examples of structurally characterized complexes with coordinated carboxamido N atoms as a part of macrocyclic and nonmacrocyclic ligand framework, while high valent iron species have been proposed on the basis of catalytic studies for a variety of oxidation systems (Marlin et al., 1999; Collins et al., 1992; Bartos et al., 1995). As part of our studies on catalysis by N4 non-porphyrin complexes (Liu et al., 2006; Yan et al., 2006), we report here the synthesis and structures of the ironIII complex with 1,2-bis(4'-tert-butylpyridine-2'-carboxamido)-4,5-dichlorobenzene (H2bbpc).
In the title compound, the ironIII ion is six-coordinated forming a distorted octahedron. Two pyridine and two deprotonated amide nitrogen atoms of the ligand are in the equatorial plane whereas the two axial sites are occupied by Cl atoms (Fig. 1) as usually observed with a Cl(1)—Fe(1)—Cl(2) angle of 151.33°, which is similar to 152.3° of [Et3NH][Fe(III)(bpb)Cl2] (Yang et al., 1991). The Fe—N(amide) and Fe—N(pyridine) distances at 2.0455 (19) Å and 2.170 (2) Å are also comparable to those of [Et3NH][Fe(III)(bpb)Cl2] (Yang et al., 1991) and [Fe(III)(bpc)Cl(DMF)] (Patra et al., 1999).
For related literature, see: Bartos et al. (1995); Che et al. (1992); Collins et al. (1992); Liu et al. (2006); Marlin et al. (1999); Patra & Mukherjee (1999); Ray et al. (1993); Yan et al. (2006); Yang et al. (1991).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL.
(C8H20N)[Fe(C26H26Cl2N4O2)Cl2]·CHCl3 | F(000) = 1812 |
Mr = 873.78 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8783 reflections |
a = 11.1740 (17) Å | θ = 1–27.5° |
b = 26.598 (4) Å | µ = 0.84 mm−1 |
c = 15.000 (2) Å | T = 294 K |
β = 108.380 (3)° | Needle, green |
V = 4230.9 (11) Å3 | 0.38 × 0.16 × 0.12 mm |
Z = 4 |
Bruker CCD area-detector diffractometer | 9757 independent reflections |
Radiation source: fine-focus sealed tube | 4586 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.082 |
φ and ω scans | θmax = 27.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.742, Tmax = 0.906 | k = −34→24 |
28612 measured reflections | l = −19→19 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.202 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0902P)2 + 1.0929P] where P = (Fo2 + 2Fc2)/3 |
9757 reflections | (Δ/σ)max = 0.001 |
461 parameters | Δρmax = 0.82 e Å−3 |
6 restraints | Δρmin = −0.72 e Å−3 |
(C8H20N)[Fe(C26H26Cl2N4O2)Cl2]·CHCl3 | V = 4230.9 (11) Å3 |
Mr = 873.78 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.1740 (17) Å | µ = 0.84 mm−1 |
b = 26.598 (4) Å | T = 294 K |
c = 15.000 (2) Å | 0.38 × 0.16 × 0.12 mm |
β = 108.380 (3)° |
Bruker CCD area-detector diffractometer | 9757 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4586 reflections with I > 2σ(I) |
Tmin = 0.742, Tmax = 0.906 | Rint = 0.082 |
28612 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 6 restraints |
wR(F2) = 0.202 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.82 e Å−3 |
9757 reflections | Δρmin = −0.72 e Å−3 |
461 parameters |
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) | |
Fe1 | 0.51046 (6) | 0.68484 (2) | 0.42776 (4) | 0.03555 (19) | |
Cl1 | 0.69772 (11) | 0.66071 (5) | 0.40275 (9) | 0.0552 (3) | |
Cl2 | 0.33154 (12) | 0.73891 (5) | 0.39800 (10) | 0.0592 (4) | |
Cl3 | 0.39772 (15) | 0.47520 (5) | 0.66487 (10) | 0.0738 (4) | |
Cl4 | 0.56072 (17) | 0.54520 (5) | 0.82960 (9) | 0.0791 (5) | |
O1 | 0.2920 (4) | 0.55604 (14) | 0.3533 (2) | 0.0769 (12) | |
O2 | 0.6434 (4) | 0.71324 (13) | 0.7157 (2) | 0.0691 (11) | |
N1 | 0.4310 (3) | 0.61699 (13) | 0.4378 (2) | 0.0403 (9) | |
N2 | 0.4232 (3) | 0.66324 (13) | 0.2817 (2) | 0.0384 (8) | |
N3 | 0.5568 (3) | 0.67498 (12) | 0.5709 (2) | 0.0394 (9) | |
N4 | 0.6103 (3) | 0.75347 (13) | 0.4854 (2) | 0.0389 (9) | |
C1 | 0.4538 (4) | 0.59680 (16) | 0.5284 (3) | 0.0392 (10) | |
C2 | 0.4177 (5) | 0.54949 (17) | 0.5499 (3) | 0.0486 (12) | |
H2 | 0.3716 | 0.5284 | 0.5019 | 0.058* | |
C3 | 0.4497 (5) | 0.53371 (17) | 0.6416 (3) | 0.0469 (12) | |
C4 | 0.5199 (5) | 0.56432 (17) | 0.7140 (3) | 0.0494 (12) | |
C5 | 0.5564 (5) | 0.61223 (16) | 0.6936 (3) | 0.0455 (11) | |
H5 | 0.6024 | 0.6331 | 0.7421 | 0.055* | |
C6 | 0.5243 (4) | 0.62872 (15) | 0.6015 (3) | 0.0377 (10) | |
C7 | 0.3580 (5) | 0.59411 (18) | 0.3598 (3) | 0.0487 (12) | |
C8 | 0.3598 (4) | 0.61986 (16) | 0.2707 (3) | 0.0403 (11) | |
C9 | 0.3016 (5) | 0.59894 (18) | 0.1842 (3) | 0.0491 (12) | |
H9 | 0.2568 | 0.5691 | 0.1800 | 0.059* | |
C10 | 0.3088 (4) | 0.62196 (17) | 0.1025 (3) | 0.0460 (11) | |
C11 | 0.3735 (5) | 0.66710 (18) | 0.1158 (3) | 0.0504 (12) | |
H11 | 0.3791 | 0.6847 | 0.0638 | 0.060* | |
C12 | 0.4295 (4) | 0.68648 (18) | 0.2039 (3) | 0.0456 (11) | |
H12 | 0.4733 | 0.7167 | 0.2099 | 0.055* | |
C13 | 0.2490 (5) | 0.59941 (19) | 0.0053 (3) | 0.0570 (13) | |
C14 | 0.1764 (6) | 0.5507 (2) | 0.0082 (4) | 0.083 (2) | |
H14A | 0.1423 | 0.5374 | −0.0542 | 0.124* | |
H14B | 0.1090 | 0.5577 | 0.0332 | 0.124* | |
H14C | 0.2326 | 0.5265 | 0.0474 | 0.124* | |
C15 | 0.1525 (6) | 0.6372 (2) | −0.0550 (4) | 0.0752 (17) | |
H15A | 0.1097 | 0.6225 | −0.1150 | 0.113* | |
H15B | 0.1955 | 0.6671 | −0.0638 | 0.113* | |
H15C | 0.0922 | 0.6455 | −0.0238 | 0.113* | |
C16 | 0.3521 (6) | 0.5890 (3) | −0.0374 (5) | 0.110 (3) | |
H16A | 0.4069 | 0.5633 | −0.0019 | 0.166* | |
H16B | 0.3997 | 0.6192 | −0.0364 | 0.166* | |
H16C | 0.3153 | 0.5780 | −0.1011 | 0.166* | |
C17 | 0.6155 (4) | 0.71209 (16) | 0.6296 (3) | 0.0424 (11) | |
C18 | 0.6447 (4) | 0.75677 (15) | 0.5787 (3) | 0.0384 (10) | |
C19 | 0.7036 (4) | 0.79860 (16) | 0.6265 (3) | 0.0416 (11) | |
H19 | 0.7253 | 0.7996 | 0.6917 | 0.050* | |
C20 | 0.7311 (4) | 0.83949 (16) | 0.5783 (3) | 0.0405 (10) | |
C21 | 0.6945 (5) | 0.83492 (18) | 0.4817 (3) | 0.0506 (12) | |
H21 | 0.7103 | 0.8612 | 0.4460 | 0.061* | |
C22 | 0.6354 (5) | 0.79231 (17) | 0.4377 (3) | 0.0500 (12) | |
H22 | 0.6121 | 0.7904 | 0.3725 | 0.060* | |
C23 | 0.7961 (5) | 0.88641 (18) | 0.6282 (3) | 0.0519 (13) | |
C24A | 0.9179 (14) | 0.8686 (6) | 0.7044 (11) | 0.0870 (19) | 0.39 |
H24A | 0.9733 | 0.8532 | 0.6748 | 0.131* | 0.39 |
H24B | 0.8966 | 0.8446 | 0.7448 | 0.131* | 0.39 |
H24C | 0.9593 | 0.8969 | 0.7409 | 0.131* | 0.39 |
C25A | 0.7102 (15) | 0.9105 (6) | 0.6776 (12) | 0.0870 (19) | 0.39 |
H25A | 0.7130 | 0.8912 | 0.7322 | 0.131* | 0.39 |
H25B | 0.6253 | 0.9114 | 0.6355 | 0.131* | 0.39 |
H25C | 0.7383 | 0.9442 | 0.6960 | 0.131* | 0.39 |
C26A | 0.8306 (18) | 0.9228 (6) | 0.5640 (11) | 0.0870 (19) | 0.39 |
H26A | 0.8734 | 0.9052 | 0.5271 | 0.131* | 0.39 |
H26B | 0.8849 | 0.9483 | 0.6007 | 0.131* | 0.39 |
H26C | 0.7554 | 0.9381 | 0.5232 | 0.131* | 0.39 |
C24B | 0.8573 (12) | 0.8799 (4) | 0.7337 (6) | 0.0870 (19) | 0.61 |
H24D | 0.9155 | 0.9069 | 0.7576 | 0.131* | 0.61 |
H24E | 0.9016 | 0.8484 | 0.7459 | 0.131* | 0.61 |
H24F | 0.7934 | 0.8802 | 0.7640 | 0.131* | 0.61 |
C25B | 0.6950 (10) | 0.9287 (4) | 0.6160 (8) | 0.0870 (19) | 0.61 |
H25D | 0.7333 | 0.9576 | 0.6524 | 0.131* | 0.61 |
H25E | 0.6277 | 0.9167 | 0.6372 | 0.131* | 0.61 |
H25F | 0.6621 | 0.9379 | 0.5509 | 0.131* | 0.61 |
C26B | 0.8916 (10) | 0.9059 (4) | 0.5842 (8) | 0.0870 (19) | 0.61 |
H26D | 0.8513 | 0.9111 | 0.5182 | 0.131* | 0.61 |
H26E | 0.9584 | 0.8818 | 0.5933 | 0.131* | 0.61 |
H26F | 0.9258 | 0.9371 | 0.6133 | 0.131* | 0.61 |
N5 | 1.0897 (4) | 0.69071 (17) | 0.5774 (3) | 0.0616 (12) | |
C27 | 1.0491 (7) | 0.6444 (3) | 0.5164 (6) | 0.098 (2) | |
H27A | 1.0520 | 0.6156 | 0.5568 | 0.117* | |
H27B | 0.9622 | 0.6488 | 0.4773 | 0.117* | |
C28 | 1.1258 (8) | 0.6334 (4) | 0.4559 (6) | 0.139 (3) | |
H28A | 1.2126 | 0.6301 | 0.4937 | 0.208* | |
H28B | 1.1178 | 0.6604 | 0.4118 | 0.208* | |
H28C | 1.0976 | 0.6026 | 0.4225 | 0.208* | |
C29 | 1.2224 (6) | 0.6877 (3) | 0.6422 (5) | 0.093 (2) | |
H29A | 1.2785 | 0.6860 | 0.6044 | 0.112* | |
H29B | 1.2413 | 0.7187 | 0.6782 | 0.112* | |
C30 | 1.2517 (8) | 0.6448 (3) | 0.7091 (6) | 0.125 (3) | |
H30A | 1.2313 | 0.6139 | 0.6748 | 0.188* | |
H30B | 1.2029 | 0.6477 | 0.7513 | 0.188* | |
H30C | 1.3399 | 0.6452 | 0.7444 | 0.188* | |
C31 | 0.9954 (6) | 0.6931 (3) | 0.6309 (6) | 0.108 (3) | |
H31A | 0.9115 | 0.6951 | 0.5857 | 0.129* | |
H31B | 1.0004 | 0.6618 | 0.6652 | 0.129* | |
C32 | 1.0105 (10) | 0.7346 (5) | 0.6971 (8) | 0.196 (6) | |
H32A | 0.9316 | 0.7410 | 0.7079 | 0.294* | |
H32B | 1.0367 | 0.7642 | 0.6716 | 0.294* | |
H32C | 1.0731 | 0.7260 | 0.7554 | 0.294* | |
C33 | 1.0820 (6) | 0.7370 (3) | 0.5178 (5) | 0.094 (2) | |
H33A | 1.1056 | 0.7658 | 0.5592 | 0.112* | |
H33B | 1.1438 | 0.7339 | 0.4851 | 0.112* | |
C34 | 0.9560 (7) | 0.7475 (3) | 0.4466 (6) | 0.118 (3) | |
H34A | 0.8935 | 0.7511 | 0.4778 | 0.177* | |
H34B | 0.9331 | 0.7202 | 0.4027 | 0.177* | |
H34C | 0.9606 | 0.7780 | 0.4136 | 0.177* | |
Cl11 | 0.19736 (18) | 0.43278 (9) | 0.41748 (17) | 0.1219 (8) | |
C35A | 0.1169 (9) | 0.4704 (3) | 0.3228 (7) | 0.162 (5) | |
H35A | 0.1603 | 0.5028 | 0.3277 | 0.194* | |
Cl2A | −0.0355 (3) | 0.48061 (12) | 0.3158 (4) | 0.248 (2) | |
Cl3A | 0.1157 (4) | 0.4405 (2) | 0.2175 (3) | 0.271 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0450 (4) | 0.0311 (3) | 0.0310 (3) | −0.0062 (3) | 0.0126 (3) | −0.0013 (3) |
Cl1 | 0.0479 (7) | 0.0577 (8) | 0.0614 (8) | −0.0011 (6) | 0.0194 (6) | −0.0077 (6) |
Cl2 | 0.0567 (8) | 0.0543 (8) | 0.0667 (9) | 0.0088 (6) | 0.0197 (7) | −0.0022 (6) |
Cl3 | 0.1042 (12) | 0.0443 (8) | 0.0731 (10) | −0.0178 (7) | 0.0286 (9) | 0.0186 (7) |
Cl4 | 0.1320 (14) | 0.0584 (9) | 0.0447 (8) | −0.0082 (8) | 0.0248 (9) | 0.0152 (6) |
O1 | 0.109 (3) | 0.065 (2) | 0.050 (2) | −0.056 (2) | 0.016 (2) | −0.0018 (18) |
O2 | 0.128 (3) | 0.048 (2) | 0.0294 (18) | −0.022 (2) | 0.021 (2) | −0.0039 (15) |
N1 | 0.048 (2) | 0.038 (2) | 0.033 (2) | −0.0066 (17) | 0.0103 (17) | 0.0019 (16) |
N2 | 0.043 (2) | 0.039 (2) | 0.034 (2) | −0.0063 (17) | 0.0134 (17) | −0.0026 (16) |
N3 | 0.052 (2) | 0.030 (2) | 0.038 (2) | −0.0045 (16) | 0.0169 (18) | −0.0001 (15) |
N4 | 0.052 (2) | 0.035 (2) | 0.0294 (19) | −0.0059 (16) | 0.0126 (17) | 0.0005 (15) |
C1 | 0.047 (3) | 0.035 (2) | 0.037 (2) | −0.001 (2) | 0.016 (2) | 0.002 (2) |
C2 | 0.064 (3) | 0.039 (3) | 0.044 (3) | −0.011 (2) | 0.019 (2) | 0.002 (2) |
C3 | 0.060 (3) | 0.033 (3) | 0.052 (3) | −0.005 (2) | 0.024 (3) | 0.006 (2) |
C4 | 0.071 (3) | 0.038 (3) | 0.042 (3) | 0.009 (2) | 0.023 (3) | 0.010 (2) |
C5 | 0.065 (3) | 0.034 (3) | 0.038 (3) | −0.003 (2) | 0.017 (2) | 0.001 (2) |
C6 | 0.048 (3) | 0.029 (2) | 0.040 (2) | 0.0003 (19) | 0.019 (2) | 0.0040 (19) |
C7 | 0.057 (3) | 0.045 (3) | 0.044 (3) | −0.020 (2) | 0.015 (2) | −0.005 (2) |
C8 | 0.046 (3) | 0.036 (3) | 0.037 (2) | −0.008 (2) | 0.010 (2) | 0.0014 (19) |
C9 | 0.060 (3) | 0.042 (3) | 0.042 (3) | −0.015 (2) | 0.012 (2) | −0.006 (2) |
C10 | 0.053 (3) | 0.044 (3) | 0.038 (3) | 0.001 (2) | 0.010 (2) | −0.003 (2) |
C11 | 0.065 (3) | 0.048 (3) | 0.036 (3) | −0.006 (2) | 0.014 (2) | 0.003 (2) |
C12 | 0.052 (3) | 0.045 (3) | 0.038 (3) | −0.013 (2) | 0.012 (2) | 0.002 (2) |
C13 | 0.070 (4) | 0.053 (3) | 0.039 (3) | 0.004 (3) | 0.005 (3) | −0.008 (2) |
C14 | 0.120 (5) | 0.049 (4) | 0.055 (4) | −0.005 (3) | −0.007 (3) | −0.006 (3) |
C15 | 0.091 (4) | 0.067 (4) | 0.051 (3) | −0.007 (3) | −0.002 (3) | −0.001 (3) |
C16 | 0.094 (5) | 0.171 (8) | 0.068 (4) | 0.013 (5) | 0.029 (4) | −0.047 (5) |
C17 | 0.058 (3) | 0.035 (3) | 0.035 (3) | −0.004 (2) | 0.015 (2) | −0.004 (2) |
C18 | 0.048 (3) | 0.033 (2) | 0.033 (2) | −0.0030 (19) | 0.012 (2) | 0.0000 (19) |
C19 | 0.054 (3) | 0.038 (3) | 0.033 (2) | −0.002 (2) | 0.014 (2) | −0.0028 (19) |
C20 | 0.049 (3) | 0.030 (2) | 0.043 (3) | −0.0030 (19) | 0.014 (2) | −0.002 (2) |
C21 | 0.072 (3) | 0.038 (3) | 0.042 (3) | −0.017 (2) | 0.018 (2) | 0.001 (2) |
C22 | 0.074 (3) | 0.043 (3) | 0.032 (2) | −0.015 (2) | 0.015 (2) | 0.001 (2) |
C23 | 0.066 (3) | 0.040 (3) | 0.050 (3) | −0.017 (2) | 0.019 (3) | −0.004 (2) |
C24A | 0.117 (5) | 0.056 (4) | 0.085 (4) | −0.029 (3) | 0.027 (4) | −0.025 (3) |
C25A | 0.117 (5) | 0.056 (4) | 0.085 (4) | −0.029 (3) | 0.027 (4) | −0.025 (3) |
C26A | 0.117 (5) | 0.056 (4) | 0.085 (4) | −0.029 (3) | 0.027 (4) | −0.025 (3) |
C24B | 0.117 (5) | 0.056 (4) | 0.085 (4) | −0.029 (3) | 0.027 (4) | −0.025 (3) |
C25B | 0.117 (5) | 0.056 (4) | 0.085 (4) | −0.029 (3) | 0.027 (4) | −0.025 (3) |
C26B | 0.117 (5) | 0.056 (4) | 0.085 (4) | −0.029 (3) | 0.027 (4) | −0.025 (3) |
N5 | 0.052 (3) | 0.065 (3) | 0.068 (3) | −0.004 (2) | 0.020 (2) | 0.002 (2) |
C27 | 0.077 (5) | 0.086 (5) | 0.122 (6) | −0.009 (4) | 0.020 (5) | 0.009 (5) |
C28 | 0.107 (6) | 0.184 (9) | 0.121 (7) | 0.043 (6) | 0.030 (6) | −0.041 (6) |
C29 | 0.067 (4) | 0.111 (6) | 0.099 (5) | 0.012 (4) | 0.023 (4) | 0.001 (4) |
C30 | 0.111 (6) | 0.156 (8) | 0.107 (6) | 0.049 (6) | 0.030 (5) | 0.034 (6) |
C31 | 0.073 (5) | 0.147 (8) | 0.108 (6) | 0.016 (5) | 0.035 (5) | 0.013 (5) |
C32 | 0.133 (9) | 0.295 (16) | 0.146 (9) | 0.091 (9) | 0.024 (7) | −0.072 (10) |
C33 | 0.081 (5) | 0.080 (5) | 0.117 (6) | −0.013 (4) | 0.026 (4) | 0.016 (4) |
C34 | 0.089 (5) | 0.107 (6) | 0.135 (7) | −0.014 (4) | 0.001 (5) | 0.051 (5) |
Cl11 | 0.0844 (13) | 0.1178 (17) | 0.1413 (19) | −0.0121 (11) | 0.0038 (12) | 0.0392 (14) |
C35A | 0.135 (8) | 0.128 (7) | 0.158 (9) | −0.092 (6) | −0.047 (6) | 0.059 (6) |
Cl2A | 0.136 (2) | 0.145 (3) | 0.414 (6) | 0.027 (2) | 0.017 (3) | 0.137 (3) |
Cl3A | 0.187 (4) | 0.410 (7) | 0.150 (3) | −0.071 (4) | −0.040 (3) | −0.039 (4) |
Fe1—N1 | 2.038 (3) | C23—C26A | 1.498 (13) |
Fe1—N3 | 2.060 (3) | C23—C26B | 1.512 (10) |
Fe1—N4 | 2.172 (3) | C23—C24B | 1.522 (10) |
Fe1—N2 | 2.176 (3) | C23—C25A | 1.526 (13) |
Fe1—Cl1 | 2.3294 (14) | C23—C24A | 1.550 (13) |
Fe1—Cl2 | 2.3879 (14) | C23—C25B | 1.564 (10) |
Cl3—C3 | 1.735 (5) | C24A—H24A | 0.9600 |
Cl4—C4 | 1.724 (5) | C24A—H24B | 0.9600 |
O1—C7 | 1.238 (5) | C24A—H24C | 0.9600 |
O2—C17 | 1.231 (5) | C25A—H25A | 0.9600 |
N1—C7 | 1.342 (5) | C25A—H25B | 0.9600 |
N1—C1 | 1.407 (5) | C25A—H25C | 0.9600 |
N2—C8 | 1.337 (5) | C26A—H26A | 0.9600 |
N2—C12 | 1.342 (5) | C26A—H26B | 0.9600 |
N3—C17 | 1.347 (5) | C26A—H26C | 0.9600 |
N3—C6 | 1.401 (5) | C24B—H24D | 0.9600 |
N4—C18 | 1.331 (5) | C24B—H24E | 0.9600 |
N4—C22 | 1.336 (5) | C24B—H24F | 0.9600 |
C1—C2 | 1.390 (6) | C25B—H25D | 0.9600 |
C1—C6 | 1.415 (6) | C25B—H25E | 0.9600 |
C2—C3 | 1.373 (6) | C25B—H25F | 0.9600 |
C2—H2 | 0.9300 | C26B—H26D | 0.9600 |
C3—C4 | 1.387 (7) | C26B—H26E | 0.9600 |
C4—C5 | 1.401 (6) | C26B—H26F | 0.9600 |
C5—C6 | 1.384 (6) | N5—C29 | 1.497 (7) |
C5—H5 | 0.9300 | N5—C33 | 1.508 (7) |
C7—C8 | 1.507 (6) | N5—C31 | 1.513 (8) |
C8—C9 | 1.374 (6) | N5—C27 | 1.516 (8) |
C9—C10 | 1.394 (6) | C27—C28 | 1.461 (10) |
C9—H9 | 0.9300 | C27—H27A | 0.9700 |
C10—C11 | 1.383 (6) | C27—H27B | 0.9700 |
C10—C13 | 1.523 (6) | C28—H28A | 0.9600 |
C11—C12 | 1.372 (6) | C28—H28B | 0.9600 |
C11—H11 | 0.9300 | C28—H28C | 0.9600 |
C12—H12 | 0.9300 | C29—C30 | 1.485 (9) |
C13—C16 | 1.510 (8) | C29—H29A | 0.9700 |
C13—C14 | 1.537 (7) | C29—H29B | 0.9700 |
C13—C15 | 1.542 (7) | C30—H30A | 0.9600 |
C14—H14A | 0.9600 | C30—H30B | 0.9600 |
C14—H14B | 0.9600 | C30—H30C | 0.9600 |
C14—H14C | 0.9600 | C31—C32 | 1.459 (11) |
C15—H15A | 0.9600 | C31—H31A | 0.9700 |
C15—H15B | 0.9600 | C31—H31B | 0.9700 |
C15—H15C | 0.9600 | C32—H32A | 0.9600 |
C16—H16A | 0.9600 | C32—H32B | 0.9600 |
C16—H16B | 0.9600 | C32—H32C | 0.9600 |
C16—H16C | 0.9600 | C33—C34 | 1.502 (9) |
C17—C18 | 1.503 (6) | C33—H33A | 0.9700 |
C18—C19 | 1.374 (6) | C33—H33B | 0.9700 |
C19—C20 | 1.393 (6) | C34—H34A | 0.9600 |
C19—H19 | 0.9300 | C34—H34B | 0.9600 |
C20—C21 | 1.381 (6) | C34—H34C | 0.9600 |
C20—C23 | 1.517 (6) | Cl11—C35A | 1.738 (8) |
C21—C22 | 1.372 (6) | C35A—Cl2A | 1.694 (11) |
C21—H21 | 0.9300 | C35A—Cl3A | 1.764 (12) |
C22—H22 | 0.9300 | C35A—H35A | 0.9800 |
N1—Fe1—N3 | 77.44 (13) | C26B—C23—C20 | 111.1 (5) |
N1—Fe1—N4 | 153.65 (13) | C26A—C23—C24B | 128.2 (9) |
N3—Fe1—N4 | 76.30 (13) | C26B—C23—C24B | 110.2 (7) |
N1—Fe1—N2 | 76.90 (13) | C20—C23—C24B | 114.0 (5) |
N3—Fe1—N2 | 154.33 (14) | C26A—C23—C25A | 111.6 (10) |
N4—Fe1—N2 | 129.33 (13) | C26B—C23—C25A | 134.9 (8) |
N1—Fe1—Cl1 | 101.69 (11) | C20—C23—C25A | 107.9 (7) |
N3—Fe1—Cl1 | 100.91 (11) | C24B—C23—C25A | 71.9 (9) |
N4—Fe1—Cl1 | 85.46 (10) | C26A—C23—C24A | 109.1 (10) |
N2—Fe1—Cl1 | 84.56 (10) | C26B—C23—C24A | 81.4 (9) |
N1—Fe1—Cl2 | 100.86 (11) | C20—C23—C24A | 106.5 (7) |
N3—Fe1—Cl2 | 101.07 (11) | C24B—C23—C24A | 36.6 (7) |
N4—Fe1—Cl2 | 82.12 (10) | C25A—C23—C24A | 108.1 (10) |
N2—Fe1—Cl2 | 83.56 (10) | C26A—C23—C25B | 77.4 (9) |
Cl1—Fe1—Cl2 | 151.34 (5) | C26B—C23—C25B | 106.6 (7) |
C7—N1—C1 | 122.9 (4) | C20—C23—C25B | 108.6 (5) |
C7—N1—Fe1 | 119.8 (3) | C24B—C23—C25B | 105.9 (7) |
C1—N1—Fe1 | 117.3 (3) | C25A—C23—C25B | 38.1 (7) |
C8—N2—C12 | 117.5 (4) | C24A—C23—C25B | 137.7 (8) |
C8—N2—Fe1 | 113.8 (3) | C23—C24A—H24A | 109.5 |
C12—N2—Fe1 | 128.6 (3) | C23—C24A—H24B | 109.5 |
C17—N3—C6 | 123.5 (4) | C23—C24A—H24C | 109.5 |
C17—N3—Fe1 | 119.9 (3) | C23—C25A—H25A | 109.5 |
C6—N3—Fe1 | 116.6 (3) | C23—C25A—H25B | 109.5 |
C18—N4—C22 | 118.2 (4) | C23—C25A—H25C | 109.5 |
C18—N4—Fe1 | 114.6 (3) | C23—C26A—H26A | 109.5 |
C22—N4—Fe1 | 127.2 (3) | C23—C26A—H26B | 109.5 |
C2—C1—N1 | 126.3 (4) | C23—C26A—H26C | 109.5 |
C2—C1—C6 | 119.7 (4) | C23—C24B—H24D | 109.5 |
N1—C1—C6 | 114.0 (4) | C23—C24B—H24E | 109.5 |
C3—C2—C1 | 120.4 (4) | H24D—C24B—H24E | 109.5 |
C3—C2—H2 | 119.8 | C23—C24B—H24F | 109.5 |
C1—C2—H2 | 119.8 | H24D—C24B—H24F | 109.5 |
C2—C3—C4 | 120.7 (4) | H24E—C24B—H24F | 109.5 |
C2—C3—Cl3 | 118.6 (4) | C23—C25B—H25D | 109.5 |
C4—C3—Cl3 | 120.7 (4) | C23—C25B—H25E | 109.5 |
C3—C4—C5 | 119.6 (4) | H25D—C25B—H25E | 109.5 |
C3—C4—Cl4 | 121.3 (4) | C23—C25B—H25F | 109.5 |
C5—C4—Cl4 | 119.1 (4) | H25D—C25B—H25F | 109.5 |
C6—C5—C4 | 120.4 (4) | H25E—C25B—H25F | 109.5 |
C6—C5—H5 | 119.8 | C23—C26B—H26D | 109.5 |
C4—C5—H5 | 119.8 | C23—C26B—H26E | 109.5 |
C5—C6—N3 | 126.4 (4) | H26D—C26B—H26E | 109.5 |
C5—C6—C1 | 119.3 (4) | C23—C26B—H26F | 109.5 |
N3—C6—C1 | 114.3 (4) | H26D—C26B—H26F | 109.5 |
O1—C7—N1 | 128.5 (4) | H26E—C26B—H26F | 109.5 |
O1—C7—C8 | 118.4 (4) | C29—N5—C33 | 106.8 (5) |
N1—C7—C8 | 113.1 (4) | C29—N5—C31 | 111.8 (5) |
N2—C8—C9 | 122.7 (4) | C33—N5—C31 | 111.1 (5) |
N2—C8—C7 | 116.0 (4) | C29—N5—C27 | 113.3 (5) |
C9—C8—C7 | 121.3 (4) | C33—N5—C27 | 110.8 (5) |
C8—C9—C10 | 120.8 (4) | C31—N5—C27 | 103.2 (5) |
C8—C9—H9 | 119.6 | C28—C27—N5 | 114.5 (6) |
C10—C9—H9 | 119.6 | C28—C27—H27A | 108.6 |
C11—C10—C9 | 115.3 (4) | N5—C27—H27A | 108.6 |
C11—C10—C13 | 122.1 (4) | C28—C27—H27B | 108.6 |
C9—C10—C13 | 122.6 (4) | N5—C27—H27B | 108.6 |
C12—C11—C10 | 121.7 (4) | H27A—C27—H27B | 107.6 |
C12—C11—H11 | 119.2 | C27—C28—H28A | 109.5 |
C10—C11—H11 | 119.2 | C27—C28—H28B | 109.5 |
N2—C12—C11 | 122.0 (4) | H28A—C28—H28B | 109.5 |
N2—C12—H12 | 119.0 | C27—C28—H28C | 109.5 |
C11—C12—H12 | 119.0 | H28A—C28—H28C | 109.5 |
C16—C13—C10 | 108.4 (5) | H28B—C28—H28C | 109.5 |
C16—C13—C14 | 109.7 (5) | C30—C29—N5 | 116.2 (6) |
C10—C13—C14 | 112.4 (4) | C30—C29—H29A | 108.2 |
C16—C13—C15 | 110.9 (5) | N5—C29—H29A | 108.2 |
C10—C13—C15 | 108.6 (4) | C30—C29—H29B | 108.2 |
C14—C13—C15 | 106.8 (5) | N5—C29—H29B | 108.2 |
C13—C14—H14A | 109.5 | H29A—C29—H29B | 107.4 |
C13—C14—H14B | 109.5 | C29—C30—H30A | 109.5 |
H14A—C14—H14B | 109.5 | C29—C30—H30B | 109.5 |
C13—C14—H14C | 109.5 | H30A—C30—H30B | 109.5 |
H14A—C14—H14C | 109.5 | C29—C30—H30C | 109.5 |
H14B—C14—H14C | 109.5 | H30A—C30—H30C | 109.5 |
C13—C15—H15A | 109.5 | H30B—C30—H30C | 109.5 |
C13—C15—H15B | 109.5 | C32—C31—N5 | 116.3 (8) |
H15A—C15—H15B | 109.5 | C32—C31—H31A | 108.2 |
C13—C15—H15C | 109.5 | N5—C31—H31A | 108.2 |
H15A—C15—H15C | 109.5 | C32—C31—H31B | 108.2 |
H15B—C15—H15C | 109.5 | N5—C31—H31B | 108.2 |
C13—C16—H16A | 109.5 | H31A—C31—H31B | 107.4 |
C13—C16—H16B | 109.5 | C31—C32—H32A | 109.5 |
H16A—C16—H16B | 109.5 | C31—C32—H32B | 109.5 |
C13—C16—H16C | 109.5 | H32A—C32—H32B | 109.5 |
H16A—C16—H16C | 109.5 | C31—C32—H32C | 109.5 |
H16B—C16—H16C | 109.5 | H32A—C32—H32C | 109.5 |
O2—C17—N3 | 127.9 (4) | H32B—C32—H32C | 109.5 |
O2—C17—C18 | 119.3 (4) | C34—C33—N5 | 116.1 (5) |
N3—C17—C18 | 112.7 (4) | C34—C33—H33A | 108.3 |
N4—C18—C19 | 122.3 (4) | N5—C33—H33A | 108.3 |
N4—C18—C17 | 116.4 (4) | C34—C33—H33B | 108.3 |
C19—C18—C17 | 121.3 (4) | N5—C33—H33B | 108.3 |
C18—C19—C20 | 120.6 (4) | H33A—C33—H33B | 107.4 |
C18—C19—H19 | 119.7 | C33—C34—H34A | 109.5 |
C20—C19—H19 | 119.7 | C33—C34—H34B | 109.5 |
C21—C20—C19 | 115.8 (4) | H34A—C34—H34B | 109.5 |
C21—C20—C23 | 121.8 (4) | C33—C34—H34C | 109.5 |
C19—C20—C23 | 122.4 (4) | H34A—C34—H34C | 109.5 |
C22—C21—C20 | 121.1 (4) | H34B—C34—H34C | 109.5 |
C22—C21—H21 | 119.5 | Cl2A—C35A—Cl11 | 113.2 (6) |
C20—C21—H21 | 119.5 | Cl2A—C35A—Cl3A | 107.0 (5) |
N4—C22—C21 | 122.1 (4) | Cl11—C35A—Cl3A | 109.2 (7) |
N4—C22—H22 | 119.0 | Cl2A—C35A—H35A | 109.1 |
C21—C22—H22 | 119.0 | Cl11—C35A—H35A | 109.1 |
C26A—C23—C26B | 30.5 (8) | Cl3A—C35A—H35A | 109.1 |
C26A—C23—C20 | 113.2 (8) |
Experimental details
Crystal data | |
Chemical formula | (C8H20N)[Fe(C26H26Cl2N4O2)Cl2]·CHCl3 |
Mr | 873.78 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 11.1740 (17), 26.598 (4), 15.000 (2) |
β (°) | 108.380 (3) |
V (Å3) | 4230.9 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.84 |
Crystal size (mm) | 0.38 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Bruker CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.742, 0.906 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28612, 9757, 4586 |
Rint | 0.082 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.202, 1.01 |
No. of reflections | 9757 |
No. of parameters | 461 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.82, −0.72 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1998), SHELXTL.
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There has been a growing interest in the coordination chemistry of peptide complexes of iron in a +3 or higher oxidation state (Marlin et al., 1999; Che et al., 1992). Mascharak and Collins have provided examples of structurally characterized complexes with coordinated carboxamido N atoms as a part of macrocyclic and nonmacrocyclic ligand framework, while high valent iron species have been proposed on the basis of catalytic studies for a variety of oxidation systems (Marlin et al., 1999; Collins et al., 1992; Bartos et al., 1995). As part of our studies on catalysis by N4 non-porphyrin complexes (Liu et al., 2006; Yan et al., 2006), we report here the synthesis and structures of the ironIII complex with 1,2-bis(4'-tert-butylpyridine-2'-carboxamido)-4,5-dichlorobenzene (H2bbpc).
In the title compound, the ironIII ion is six-coordinated forming a distorted octahedron. Two pyridine and two deprotonated amide nitrogen atoms of the ligand are in the equatorial plane whereas the two axial sites are occupied by Cl atoms (Fig. 1) as usually observed with a Cl(1)—Fe(1)—Cl(2) angle of 151.33°, which is similar to 152.3° of [Et3NH][Fe(III)(bpb)Cl2] (Yang et al., 1991). The Fe—N(amide) and Fe—N(pyridine) distances at 2.0455 (19) Å and 2.170 (2) Å are also comparable to those of [Et3NH][Fe(III)(bpb)Cl2] (Yang et al., 1991) and [Fe(III)(bpc)Cl(DMF)] (Patra et al., 1999).