Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031084/hg2092sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031084/hg2092Isup2.hkl |
CCDC reference: 621352
Key indicators
- Single-crystal X-ray study
- T = 85 K
- Mean (C-C) = 0.002 Å
- R factor = 0.019
- wR factor = 0.047
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.775 0.827 Tmin and Tmax expected: 0.740 0.869 RR = 1.101 Please check that your absorption correction is appropriate. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.05 PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.051 Tmax scaled 0.869 Tmin scaled 0.815 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.37 From the CIF: _reflns_number_total 2581 Count of symmetry unique reflns 1395 Completeness (_total/calc) 185.02% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1186 Fraction of Friedel pairs measured 0.850 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Version 1.4.1; Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Fe(C5H5)(C11H9N2O)] | Dx = 1.583 Mg m−3 |
Mr = 306.14 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 8192 reflections |
a = 10.5859 (1) Å | θ = 1.6–26.4° |
b = 12.6355 (1) Å | µ = 1.17 mm−1 |
c = 9.6041 (1) Å | T = 85 K |
V = 1284.63 (2) Å3 | Plate, orange |
Z = 4 | 0.28 × 0.22 × 0.12 mm |
F(000) = 632 |
Siemens SMART CCD diffractometer | 2581 independent reflections |
Radiation source: fine-focus sealed tube | 2471 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 26.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.775, Tmax = 0.827 | k = −15→15 |
11891 measured reflections | l = −11→11 |
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)] = 0.019 | H-atom parameters constrained |
wR(F2) = 0.047 | w = 1/[σ2(Fo2) + (0.0225P)2 + 0.372P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2581 reflections | Δρmax = 0.26 e Å−3 |
181 parameters | Δρmin = −0.21 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1188 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.023 (12) |
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 | ||
Fe1 | 0.463957 (18) | 0.343269 (15) | 0.36538 (3) | 0.01272 (7) | |
C4 | 0.62594 (14) | 0.43244 (11) | 0.3684 (3) | 0.0170 (3) | |
H4 | 0.6791 | 0.4457 | 0.2933 | 0.020* | |
C5 | 0.63574 (16) | 0.34538 (13) | 0.46385 (19) | 0.0154 (3) | |
C9 | 0.33799 (14) | 0.22030 (12) | 0.3624 (3) | 0.0177 (3) | |
H9 | 0.3159 | 0.1782 | 0.4381 | 0.021* | |
C14 | 0.87401 (15) | −0.05945 (13) | 0.68432 (19) | 0.0148 (3) | |
H14 | 0.8558 | −0.1087 | 0.7534 | 0.018* | |
C2 | 0.46498 (16) | 0.44726 (14) | 0.5291 (2) | 0.0181 (4) | |
H2 | 0.3948 | 0.4724 | 0.5771 | 0.022* | |
C3 | 0.51980 (17) | 0.49511 (14) | 0.40936 (19) | 0.0189 (4) | |
H3 | 0.4916 | 0.5563 | 0.3655 | 0.023* | |
C10 | 0.27728 (16) | 0.31615 (14) | 0.32164 (19) | 0.0191 (4) | |
H10 | 0.2085 | 0.3473 | 0.3657 | 0.023* | |
C8 | 0.43834 (16) | 0.20034 (14) | 0.2671 (2) | 0.0178 (4) | |
H8 | 0.4930 | 0.1427 | 0.2695 | 0.021* | |
O1 | 0.82610 (10) | 0.27651 (9) | 0.37100 (19) | 0.0233 (3) | |
N1 | 0.98275 (13) | −0.07113 (12) | 0.61244 (16) | 0.0160 (3) | |
N2 | 0.72474 (13) | 0.17807 (11) | 0.53795 (16) | 0.0153 (3) | |
H2A | 0.6562 | 0.1742 | 0.5857 | 0.018* | |
C13 | 0.78782 (15) | 0.02137 (14) | 0.66159 (18) | 0.0153 (3) | |
H13 | 0.7150 | 0.0260 | 0.7154 | 0.018* | |
C1 | 0.53520 (16) | 0.35447 (14) | 0.5634 (2) | 0.0161 (4) | |
H1 | 0.5188 | 0.3084 | 0.6367 | 0.019* | |
C12 | 0.81157 (16) | 0.09614 (14) | 0.55662 (18) | 0.0137 (3) | |
C11 | 0.73691 (16) | 0.26463 (13) | 0.45113 (18) | 0.0148 (3) | |
C15 | 1.00192 (17) | 0.00008 (15) | 0.51100 (19) | 0.0152 (3) | |
H15 | 1.0756 | −0.0065 | 0.4590 | 0.018* | |
C16 | 0.92109 (16) | 0.08296 (14) | 0.47675 (19) | 0.0145 (3) | |
H16 | 0.9393 | 0.1282 | 0.4031 | 0.017* | |
C6 | 0.34099 (17) | 0.35592 (14) | 0.2009 (2) | 0.0191 (4) | |
H6 | 0.3211 | 0.4176 | 0.1529 | 0.023* | |
C7 | 0.44046 (17) | 0.28394 (14) | 0.16752 (19) | 0.0193 (4) | |
H7 | 0.4968 | 0.2905 | 0.0937 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.01237 (10) | 0.01277 (11) | 0.01302 (11) | 0.00078 (8) | −0.00028 (12) | −0.00064 (13) |
C4 | 0.0170 (7) | 0.0149 (7) | 0.0191 (8) | −0.0026 (5) | −0.0011 (10) | 0.0024 (10) |
C5 | 0.0145 (8) | 0.0161 (8) | 0.0156 (9) | −0.0027 (6) | −0.0037 (7) | 0.0002 (7) |
C9 | 0.0169 (7) | 0.0168 (7) | 0.0194 (8) | −0.0036 (6) | −0.0028 (9) | −0.0019 (10) |
C14 | 0.0148 (8) | 0.0148 (8) | 0.0148 (9) | −0.0022 (6) | −0.0006 (7) | 0.0009 (7) |
C2 | 0.0190 (9) | 0.0173 (9) | 0.0180 (9) | 0.0005 (7) | −0.0012 (7) | −0.0074 (7) |
C3 | 0.0211 (9) | 0.0121 (8) | 0.0236 (10) | −0.0010 (7) | −0.0049 (7) | −0.0003 (6) |
C10 | 0.0132 (8) | 0.0214 (9) | 0.0226 (10) | 0.0002 (7) | −0.0033 (6) | −0.0027 (7) |
C8 | 0.0194 (8) | 0.0147 (8) | 0.0192 (9) | 0.0019 (7) | −0.0041 (7) | −0.0041 (7) |
O1 | 0.0165 (5) | 0.0258 (6) | 0.0276 (7) | 0.0025 (4) | 0.0057 (7) | 0.0110 (8) |
N1 | 0.0153 (7) | 0.0156 (7) | 0.0172 (8) | 0.0000 (6) | −0.0012 (6) | −0.0014 (6) |
N2 | 0.0112 (7) | 0.0168 (7) | 0.0180 (8) | 0.0012 (5) | 0.0022 (6) | 0.0027 (6) |
C13 | 0.0118 (7) | 0.0195 (9) | 0.0146 (9) | −0.0009 (6) | 0.0007 (6) | −0.0006 (7) |
C1 | 0.0169 (8) | 0.0170 (9) | 0.0144 (9) | −0.0017 (7) | −0.0019 (7) | −0.0017 (7) |
C12 | 0.0125 (8) | 0.0141 (8) | 0.0145 (9) | −0.0015 (6) | −0.0034 (6) | −0.0002 (7) |
C11 | 0.0140 (8) | 0.0162 (8) | 0.0141 (9) | −0.0030 (7) | −0.0028 (6) | −0.0001 (7) |
C15 | 0.0116 (7) | 0.0187 (8) | 0.0154 (8) | 0.0003 (6) | 0.0015 (6) | −0.0031 (7) |
C16 | 0.0134 (8) | 0.0161 (8) | 0.0139 (8) | −0.0018 (7) | −0.0016 (7) | 0.0003 (7) |
C6 | 0.0194 (8) | 0.0207 (9) | 0.0171 (10) | 0.0019 (7) | −0.0044 (7) | −0.0012 (8) |
C7 | 0.0219 (9) | 0.0202 (9) | 0.0157 (9) | 0.0007 (7) | −0.0019 (7) | −0.0040 (7) |
Fe1—C1 | 2.0504 (18) | N2—C11 | 1.381 (2) |
Fe1—C2 | 2.0490 (18) | N2—C12 | 1.396 (2) |
Fe1—C3 | 2.0515 (18) | C13—C12 | 1.404 (2) |
Fe1—C4 | 2.0520 (14) | C14—C13 | 1.387 (2) |
Fe1—C5 | 2.0498 (17) | C14—N1 | 1.350 (2) |
Fe1—C6 | 2.0531 (18) | N1—C15 | 1.342 (2) |
Fe1—C7 | 2.0579 (18) | C15—C16 | 1.392 (3) |
Fe1—C8 | 2.0556 (18) | C12—C16 | 1.400 (2) |
Fe1—C9 | 2.0477 (15) | C4—H4 | 0.9300 |
Fe1—C10 | 2.0492 (17) | C9—H9 | 0.9300 |
C2—C1 | 1.427 (2) | C14—H14 | 0.9300 |
C2—C3 | 1.423 (3) | C2—H2 | 0.9300 |
C4—C3 | 1.430 (2) | C3—H3 | 0.9300 |
C4—C5 | 1.436 (3) | C10—H10 | 0.9300 |
C5—C1 | 1.435 (3) | C8—H8 | 0.9300 |
C6—C7 | 1.428 (3) | N2—H2A | 0.8600 |
C8—C7 | 1.425 (3) | C13—H13 | 0.9300 |
C9—C8 | 1.425 (3) | C1—H1 | 0.9300 |
C9—C10 | 1.426 (2) | C15—H15 | 0.9300 |
C10—C6 | 1.432 (3) | C16—H16 | 0.9300 |
C5—C11 | 1.484 (2) | C6—H6 | 0.9300 |
O1—C11 | 1.227 (2) | C7—H7 | 0.9300 |
C9—Fe1—C2 | 120.04 (8) | N1—C14—H14 | 117.9 |
C9—Fe1—C10 | 40.74 (7) | C13—C14—H14 | 117.9 |
C2—Fe1—C10 | 105.64 (7) | C3—C2—C1 | 108.85 (16) |
C9—Fe1—C5 | 126.44 (7) | C3—C2—Fe1 | 69.79 (10) |
C2—Fe1—C5 | 68.47 (7) | C1—C2—Fe1 | 69.68 (10) |
C10—Fe1—C5 | 162.23 (7) | C3—C2—H2 | 125.6 |
C9—Fe1—C1 | 107.74 (9) | C1—C2—H2 | 125.6 |
C2—Fe1—C1 | 40.74 (7) | Fe1—C2—H2 | 126.5 |
C10—Fe1—C1 | 123.81 (7) | C2—C3—C4 | 107.92 (17) |
C5—Fe1—C1 | 40.97 (7) | C2—C3—Fe1 | 69.60 (10) |
C9—Fe1—C3 | 154.17 (7) | C4—C3—Fe1 | 69.62 (9) |
C2—Fe1—C3 | 40.60 (7) | C2—C3—H3 | 126.0 |
C10—Fe1—C3 | 118.45 (7) | C4—C3—H3 | 126.0 |
C5—Fe1—C3 | 68.73 (7) | Fe1—C3—H3 | 126.3 |
C1—Fe1—C3 | 68.81 (7) | C9—C10—C6 | 107.95 (17) |
C9—Fe1—C4 | 163.95 (6) | C9—C10—Fe1 | 69.58 (9) |
C2—Fe1—C4 | 68.45 (8) | C6—C10—Fe1 | 69.71 (10) |
C10—Fe1—C4 | 154.23 (7) | C9—C10—H10 | 126.0 |
C5—Fe1—C4 | 40.98 (7) | C6—C10—H10 | 126.0 |
C1—Fe1—C4 | 69.01 (9) | Fe1—C10—H10 | 126.3 |
C3—Fe1—C4 | 40.79 (7) | C9—C8—C7 | 108.17 (16) |
C9—Fe1—C6 | 68.63 (8) | C9—C8—Fe1 | 69.38 (10) |
C2—Fe1—C6 | 122.94 (7) | C7—C8—Fe1 | 69.81 (10) |
C10—Fe1—C6 | 40.87 (7) | C9—C8—H8 | 125.9 |
C5—Fe1—C6 | 156.40 (8) | C7—C8—H8 | 125.9 |
C1—Fe1—C6 | 160.27 (7) | Fe1—C8—H8 | 126.5 |
C3—Fe1—C6 | 105.56 (7) | C15—N1—C14 | 115.27 (15) |
C4—Fe1—C6 | 119.86 (8) | C11—N2—C12 | 127.10 (14) |
C9—Fe1—C8 | 40.63 (8) | C11—N2—H2A | 116.4 |
C2—Fe1—C8 | 156.40 (8) | C12—N2—H2A | 116.4 |
C10—Fe1—C8 | 68.39 (7) | C14—C13—C12 | 119.38 (16) |
C5—Fe1—C8 | 109.89 (7) | C14—C13—H13 | 120.3 |
C1—Fe1—C8 | 122.34 (7) | C12—C13—H13 | 120.3 |
C3—Fe1—C8 | 162.58 (8) | C2—C1—C5 | 107.37 (16) |
C4—Fe1—C8 | 126.80 (8) | C2—C1—Fe1 | 69.58 (10) |
C6—Fe1—C8 | 68.38 (7) | C5—C1—Fe1 | 69.49 (10) |
C9—Fe1—C7 | 68.42 (9) | C2—C1—H1 | 126.3 |
C2—Fe1—C7 | 160.52 (7) | C5—C1—H1 | 126.3 |
C10—Fe1—C7 | 68.48 (7) | Fe1—C1—H1 | 126.2 |
C5—Fe1—C7 | 122.54 (7) | N2—C12—C16 | 124.27 (16) |
C1—Fe1—C7 | 157.80 (7) | N2—C12—C13 | 118.24 (16) |
C3—Fe1—C7 | 124.45 (7) | C16—C12—C13 | 117.49 (16) |
C4—Fe1—C7 | 108.30 (9) | O1—C11—N2 | 123.17 (15) |
C6—Fe1—C7 | 40.65 (7) | O1—C11—C5 | 121.51 (15) |
C8—Fe1—C7 | 40.54 (7) | N2—C11—C5 | 115.29 (15) |
C3—C4—C5 | 107.77 (18) | N1—C15—C16 | 125.68 (17) |
C3—C4—Fe1 | 69.59 (9) | N1—C15—H15 | 117.2 |
C5—C4—Fe1 | 69.43 (9) | C16—C15—H15 | 117.2 |
C3—C4—H4 | 126.1 | C15—C16—C12 | 117.97 (16) |
C5—C4—H4 | 126.1 | C15—C16—H16 | 121.0 |
Fe1—C4—H4 | 126.4 | C12—C16—H16 | 121.0 |
C1—C5—C4 | 108.08 (15) | C7—C6—C10 | 107.79 (16) |
C1—C5—C11 | 130.17 (16) | C7—C6—Fe1 | 69.85 (10) |
C4—C5—C11 | 121.75 (17) | C10—C6—Fe1 | 69.41 (10) |
C1—C5—Fe1 | 69.53 (10) | C7—C6—H6 | 126.1 |
C4—C5—Fe1 | 69.59 (9) | C10—C6—H6 | 126.1 |
C11—C5—Fe1 | 126.39 (12) | Fe1—C6—H6 | 126.2 |
C8—C9—C10 | 108.05 (19) | C8—C7—C6 | 108.04 (16) |
C8—C9—Fe1 | 69.98 (10) | C8—C7—Fe1 | 69.64 (10) |
C10—C9—Fe1 | 69.69 (9) | C6—C7—Fe1 | 69.49 (10) |
C8—C9—H9 | 126.0 | C8—C7—H7 | 126.0 |
C10—C9—H9 | 126.0 | C6—C7—H7 | 126.0 |
Fe1—C9—H9 | 125.9 | Fe1—C7—H7 | 126.5 |
N1—C14—C13 | 124.12 (16) |
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