Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026084/om6194sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026084/om6194Isup2.hkl |
CCDC reference: 231806
Key indicators
- Single-crystal X-ray study
- T = 150 K
- R factor = 0.026
- wR factor = 0.062
- Data-to-parameter ratio = 25.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.80
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT and SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: enCIFer (CCDC, 2003) and PLATON (Spek, 2003).
[Fe(C5H5)(C9H15N)]I3 | F(000) = 1184 |
Mr = 638.86 | Dx = 2.228 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7671 reflections |
a = 11.6959 (9) Å | θ = 2.3–27.6° |
b = 10.6136 (9) Å | µ = 5.64 mm−1 |
c = 15.3474 (12) Å | T = 150 K |
β = 91.638 (2)° | Block, red |
V = 1904.4 (3) Å3 | 0.50 × 0.36 × 0.30 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 4393 independent reflections |
Radiation source: normal-focus sealed tube | 3925 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.6°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −15→14 |
Tmin = 0.064, Tmax = 0.180 | k = −13→12 |
13480 measured reflections | l = −20→19 |
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)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.062 | w = 1/[σ2(Fo2) + (0.029P)2 + 2.356P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
4393 reflections | Δρmax = 1.08 e Å−3 |
173 parameters | Δρmin = −1.18 e Å−3 |
113 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00106 (8) |
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. |
x | y | z | Uiso*/Ueq | ||
Fe | 0.57586 (4) | 0.41067 (4) | 0.25079 (2) | 0.01770 (10) | |
C1 | 0.4474 (3) | 0.3846 (3) | 0.16064 (17) | 0.0184 (6) | |
C2 | 0.5574 (3) | 0.3775 (3) | 0.12134 (18) | 0.0235 (6) | |
H2 | 0.5886 | 0.3037 | 0.0892 | 0.028* | |
C3 | 0.6139 (3) | 0.4952 (3) | 0.1362 (2) | 0.0287 (7) | |
H3 | 0.6922 | 0.5178 | 0.1170 | 0.034* | |
C4 | 0.5408 (3) | 0.5734 (3) | 0.1841 (2) | 0.0315 (7) | |
H4 | 0.5592 | 0.6605 | 0.2050 | 0.038* | |
C5 | 0.4381 (3) | 0.5074 (3) | 0.1987 (2) | 0.0243 (6) | |
H5 | 0.3716 | 0.5396 | 0.2317 | 0.029* | |
C6 | 0.5635 (3) | 0.2764 (4) | 0.3459 (2) | 0.0351 (8) | |
H6 | 0.5019 | 0.2116 | 0.3500 | 0.042* | |
C7 | 0.6673 (3) | 0.2630 (4) | 0.3009 (2) | 0.0371 (8) | |
H7 | 0.6908 | 0.1867 | 0.2676 | 0.044* | |
C8 | 0.7307 (3) | 0.3744 (4) | 0.3096 (2) | 0.0387 (9) | |
H8 | 0.8074 | 0.3913 | 0.2848 | 0.046* | |
C9 | 0.6666 (3) | 0.4582 (4) | 0.3613 (2) | 0.0403 (9) | |
H9 | 0.6899 | 0.5454 | 0.3790 | 0.048* | |
C10 | 0.5626 (3) | 0.3968 (4) | 0.3829 (2) | 0.0384 (9) | |
H10 | 0.5003 | 0.4333 | 0.4184 | 0.046* | |
N12 | 0.2867 (2) | 0.2681 (3) | 0.08344 (16) | 0.0237 (6) | |
C11 | 0.3607 (3) | 0.2830 (3) | 0.16649 (18) | 0.0217 (6) | |
H11A | 0.3105 | 0.3013 | 0.2158 | 0.026* | |
H11B | 0.4002 | 0.2023 | 0.1791 | 0.026* | |
C13 | 0.1944 (3) | 0.1737 (3) | 0.1018 (2) | 0.0315 (8) | |
H13A | 0.1455 | 0.1623 | 0.0494 | 0.047* | |
H13B | 0.1481 | 0.2044 | 0.1496 | 0.047* | |
H13C | 0.2294 | 0.0929 | 0.1182 | 0.047* | |
C14 | 0.3576 (3) | 0.2202 (4) | 0.0107 (2) | 0.0369 (8) | |
H14A | 0.3095 | 0.2109 | −0.0422 | 0.055* | |
H14B | 0.3904 | 0.1382 | 0.0269 | 0.055* | |
H14C | 0.4194 | 0.2800 | −0.0001 | 0.055* | |
C15 | 0.2323 (3) | 0.3907 (3) | 0.0578 (2) | 0.0311 (8) | |
H15A | 0.1853 | 0.3790 | 0.0046 | 0.047* | |
H15B | 0.2919 | 0.4533 | 0.0474 | 0.047* | |
H15C | 0.1839 | 0.4200 | 0.1049 | 0.047* | |
I1 | 0.57558 (2) | 0.08364 (2) | −0.202225 (17) | 0.03604 (8) | |
I2 | 0.733082 (18) | 0.20712 (2) | −0.070191 (13) | 0.02773 (7) | |
I3 | 0.88581 (2) | 0.31936 (3) | 0.057543 (16) | 0.03910 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe | 0.0160 (2) | 0.0243 (2) | 0.01252 (18) | 0.00239 (16) | −0.00494 (15) | −0.00021 (15) |
C1 | 0.0202 (14) | 0.0222 (14) | 0.0125 (12) | 0.0032 (11) | −0.0050 (10) | 0.0003 (11) |
C2 | 0.0229 (15) | 0.0344 (17) | 0.0131 (12) | 0.0061 (13) | −0.0025 (11) | −0.0013 (12) |
C3 | 0.0256 (16) | 0.0373 (19) | 0.0231 (14) | −0.0037 (14) | −0.0033 (12) | 0.0122 (13) |
C4 | 0.0332 (18) | 0.0236 (16) | 0.0369 (17) | 0.0002 (14) | −0.0115 (15) | 0.0073 (13) |
C5 | 0.0225 (15) | 0.0246 (16) | 0.0254 (14) | 0.0071 (12) | −0.0079 (12) | −0.0042 (12) |
C6 | 0.0342 (18) | 0.046 (2) | 0.0243 (15) | −0.0063 (16) | −0.0121 (14) | 0.0163 (14) |
C7 | 0.039 (2) | 0.043 (2) | 0.0280 (16) | 0.0157 (16) | −0.0131 (15) | 0.0068 (15) |
C8 | 0.0179 (15) | 0.071 (3) | 0.0267 (16) | 0.0015 (16) | −0.0113 (13) | 0.0154 (17) |
C9 | 0.046 (2) | 0.051 (2) | 0.0229 (15) | −0.0084 (18) | −0.0211 (15) | −0.0014 (15) |
C10 | 0.0369 (19) | 0.063 (2) | 0.0146 (13) | 0.0048 (18) | −0.0078 (13) | 0.0006 (15) |
N12 | 0.0231 (13) | 0.0286 (14) | 0.0187 (12) | −0.0020 (11) | −0.0121 (10) | 0.0032 (10) |
C11 | 0.0234 (15) | 0.0271 (16) | 0.0140 (12) | 0.0001 (12) | −0.0095 (11) | 0.0021 (11) |
C13 | 0.0296 (18) | 0.0293 (17) | 0.0346 (17) | −0.0066 (14) | −0.0161 (14) | 0.0049 (14) |
C14 | 0.043 (2) | 0.048 (2) | 0.0186 (15) | −0.0024 (18) | −0.0062 (14) | −0.0087 (14) |
C15 | 0.0320 (18) | 0.0308 (18) | 0.0296 (16) | 0.0018 (14) | −0.0149 (14) | 0.0120 (14) |
I1 | 0.02726 (13) | 0.03188 (13) | 0.04844 (15) | 0.00596 (9) | −0.00824 (10) | 0.00393 (10) |
I2 | 0.02294 (11) | 0.02951 (12) | 0.03092 (12) | 0.00938 (8) | 0.00389 (8) | 0.00381 (8) |
I3 | 0.02922 (13) | 0.04378 (15) | 0.04403 (14) | 0.00875 (10) | −0.00385 (10) | −0.00688 (11) |
Fe—C1 | 2.032 (3) | C8—H8 | 1.0000 |
Fe—C2 | 2.023 (3) | C9—C10 | 1.427 (6) |
Fe—C3 | 2.034 (3) | C9—H9 | 1.0000 |
Fe—C4 | 2.043 (3) | C10—H10 | 1.0000 |
Fe—C5 | 2.053 (3) | C10—C6 | 1.399 (6) |
Fe—C6 | 2.048 (3) | C1—C11 | 1.486 (4) |
Fe—C7 | 2.036 (3) | C11—H11A | 0.9900 |
Fe—C8 | 2.037 (3) | C11—H11B | 0.9900 |
Fe—C9 | 2.038 (3) | C11—N12 | 1.528 (3) |
Fe—C10 | 2.044 (3) | N12—C15 | 1.496 (4) |
C1—C2 | 1.438 (4) | N12—C14 | 1.499 (4) |
C2—C3 | 1.428 (5) | N12—C13 | 1.505 (4) |
C2—H2 | 1.0000 | C13—H13A | 0.9800 |
C3—C4 | 1.412 (5) | C13—H13B | 0.9800 |
C3—H3 | 1.0000 | C13—H13C | 0.9800 |
C4—C5 | 1.415 (5) | C14—H14A | 0.9800 |
C4—H4 | 1.0000 | C14—H14B | 0.9800 |
C5—H5 | 1.0000 | C14—H14C | 0.9800 |
C5—C1 | 1.433 (4) | C15—H15A | 0.9800 |
C6—C7 | 1.421 (5) | C15—H15B | 0.9800 |
C6—H6 | 1.0000 | C15—H15C | 0.9800 |
C7—C8 | 1.400 (6) | I1—I2 | 3.0006 (4) |
C7—H7 | 1.0000 | I2—I3 | 2.8728 (4) |
C8—C9 | 1.420 (6) | ||
I3···C15i | 3.791 (3) | I1···H13Civ | 3.19 |
I1···H4i | 3.14 | I1···H15Ciii | 3.25 |
I1···H8ii | 3.15 | I2···H2 | 3.18 |
I1···H11Aiii | 3.29 | I2···H13Civ | 3.30 |
I1···H11Biv | 3.07 | I3···H3 | 3.24 |
I1···H13Biii | 3.33 | I3···H9v | 3.20 |
C2—Fe—C1 | 41.56 (12) | Fe—C4—H4 | 125.6 |
C2—Fe—C3 | 41.22 (14) | C4—C5—C1 | 108.1 (3) |
C1—Fe—C3 | 69.33 (12) | C4—C5—Fe | 69.42 (18) |
C2—Fe—C7 | 106.07 (14) | C1—C5—Fe | 68.65 (16) |
C1—Fe—C7 | 121.51 (14) | C4—C5—H5 | 125.9 |
C3—Fe—C7 | 122.72 (15) | C1—C5—H5 | 125.9 |
C2—Fe—C8 | 118.07 (14) | Fe—C5—H5 | 125.9 |
C1—Fe—C8 | 155.05 (15) | C10—C6—C7 | 107.8 (3) |
C3—Fe—C8 | 104.64 (14) | C10—C6—Fe | 69.9 (2) |
C7—Fe—C8 | 40.22 (17) | C7—C6—Fe | 69.2 (2) |
C2—Fe—C9 | 153.98 (15) | C10—C6—H6 | 126.1 |
C1—Fe—C9 | 163.23 (15) | C7—C6—H6 | 126.1 |
C3—Fe—C9 | 119.26 (15) | Fe—C6—H6 | 126.1 |
C7—Fe—C9 | 67.72 (16) | C8—C7—C6 | 109.1 (4) |
C8—Fe—C9 | 40.80 (17) | C8—C7—Fe | 69.9 (2) |
C2—Fe—C4 | 68.96 (14) | C6—C7—Fe | 70.1 (2) |
C1—Fe—C4 | 68.90 (13) | C8—C7—H7 | 125.5 |
C3—Fe—C4 | 40.52 (15) | C6—C7—H7 | 125.5 |
C7—Fe—C4 | 159.33 (16) | Fe—C7—H7 | 125.5 |
C8—Fe—C4 | 123.00 (16) | C7—C8—C9 | 107.2 (3) |
C9—Fe—C4 | 107.45 (16) | C7—C8—Fe | 69.85 (19) |
C2—Fe—C10 | 162.37 (15) | C9—C8—Fe | 69.65 (19) |
C1—Fe—C10 | 126.19 (14) | C7—C8—H8 | 126.4 |
C3—Fe—C10 | 156.07 (16) | C9—C8—H8 | 126.4 |
C7—Fe—C10 | 67.90 (16) | Fe—C8—H8 | 126.4 |
C8—Fe—C10 | 68.80 (15) | C8—C9—C10 | 108.1 (4) |
C9—Fe—C10 | 40.91 (16) | C8—C9—Fe | 69.55 (19) |
C4—Fe—C10 | 122.56 (16) | C10—C9—Fe | 69.76 (19) |
C2—Fe—C6 | 124.81 (15) | C8—C9—H9 | 125.9 |
C1—Fe—C6 | 108.95 (13) | C10—C9—H9 | 125.9 |
C3—Fe—C6 | 160.81 (16) | Fe—C9—H9 | 125.9 |
C7—Fe—C6 | 40.72 (15) | C6—C10—C9 | 107.8 (4) |
C8—Fe—C6 | 68.45 (15) | C6—C10—Fe | 70.16 (19) |
C9—Fe—C6 | 67.96 (16) | C9—C10—Fe | 69.33 (19) |
C4—Fe—C6 | 158.14 (16) | C6—C10—H10 | 126.1 |
C10—Fe—C6 | 39.99 (16) | C9—C10—H10 | 126.1 |
C2—Fe—C5 | 69.17 (12) | Fe—C10—H10 | 126.1 |
C1—Fe—C5 | 41.08 (12) | C15—N12—C14 | 109.9 (3) |
C3—Fe—C5 | 68.38 (13) | C15—N12—C13 | 109.0 (3) |
C7—Fe—C5 | 158.42 (15) | C14—N12—C13 | 109.2 (3) |
C8—Fe—C5 | 160.89 (16) | C15—N12—C11 | 110.8 (2) |
C9—Fe—C5 | 125.76 (15) | C14—N12—C11 | 110.1 (2) |
C4—Fe—C5 | 40.40 (14) | C13—N12—C11 | 107.8 (2) |
C10—Fe—C5 | 109.96 (14) | C1—C11—N12 | 113.3 (2) |
C6—Fe—C5 | 123.70 (14) | C1—C11—H11A | 108.9 |
C5—C1—C2 | 107.4 (3) | N12—C11—H11A | 108.9 |
C5—C1—C11 | 125.1 (3) | C1—C11—H11B | 108.9 |
C2—C1—C11 | 127.4 (3) | N12—C11—H11B | 108.9 |
C5—C1—Fe | 70.28 (16) | H11A—C11—H11B | 107.7 |
C2—C1—Fe | 68.91 (16) | N12—C13—H13A | 109.5 |
C11—C1—Fe | 123.41 (19) | N12—C13—H13B | 109.5 |
C3—C2—C1 | 107.5 (3) | H13A—C13—H13B | 109.5 |
C3—C2—Fe | 69.81 (17) | N12—C13—H13C | 109.5 |
C1—C2—Fe | 69.54 (15) | H13A—C13—H13C | 109.5 |
C3—C2—H2 | 126.2 | H13B—C13—H13C | 109.5 |
C1—C2—H2 | 126.2 | N12—C14—H14A | 109.5 |
Fe—C2—H2 | 126.2 | N12—C14—H14B | 109.5 |
C4—C3—C2 | 108.3 (3) | H14A—C14—H14B | 109.5 |
C4—C3—Fe | 70.08 (19) | N12—C14—H14C | 109.5 |
C2—C3—Fe | 68.97 (17) | H14A—C14—H14C | 109.5 |
C4—C3—H3 | 125.9 | H14B—C14—H14C | 109.5 |
C2—C3—H3 | 125.9 | N12—C15—H15A | 109.5 |
Fe—C3—H3 | 125.9 | N12—C15—H15B | 109.5 |
C3—C4—C5 | 108.7 (3) | H15A—C15—H15B | 109.5 |
C3—C4—Fe | 69.40 (19) | N12—C15—H15C | 109.5 |
C5—C4—Fe | 70.18 (18) | H15A—C15—H15C | 109.5 |
C3—C4—H4 | 125.6 | H15B—C15—H15C | 109.5 |
C5—C4—H4 | 125.6 | I1—I2—I3 | 178.600 (10) |
C5—C1—C11—N12 | 102.1 (3) | C14—N12—C11—C1 | 67.6 (3) |
C2—C1—C11—N12 | −81.8 (4) | C13—N12—C11—C1 | −173.4 (3) |
C15—N12—C11—C1 | −54.2 (4) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+1, −y, −z; (v) −x+3/2, y−1/2, −z+1/2. |
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