From ferrocene to fluorine-containing penta-substituted derivatives and all points in-between; or, how to increase the available chemical space.
Tazi, Mehdi; Erb, William; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence; Low, Paul J.; Organic & biomolecular chemistry 17 (2019) 9352–9359; doi:10.1039/c9ob01885a

data_7157134
_publ_section_title
;
 From ferrocene to fluorine-containing penta-substituted derivatives and
 all points in-between; or, how to increase the available chemical space.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9352
_journal_page_last               9359
_journal_paper_doi               10.1039/c9ob01885a
_journal_volume                  17
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H16 F Fe I O2 Si'
_chemical_formula_sum            'C14 H16 F Fe I O2 Si'
_chemical_formula_weight         446.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-07-08 deposited with the CCDC.    2019-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.433(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7304(10)
_cell_length_b                   13.738(3)
_cell_length_c                   17.564(3)
_cell_measurement_reflns_used    8868
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.5287
_cell_measurement_theta_min      2.3581
_cell_measurement_wavelength     0.71073
_cell_volume                     1597.2(5)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_min         2.358
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.960
_exptl_absorpt_correction_T_max  0.587
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.180
_refine_diff_density_max         1.750
_refine_diff_density_min         -1.353
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       0.0121(6)
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.530
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.530
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0220P)^2^+1.9053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3385
_reflns_number_total             3654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob01885a2.cif
_cod_data_source_block           5s-I-5_MT383
_cod_depositor_comments
'Adding full bibliography for 7157127--7157141.cif.'
_cod_database_code               7157134
_shelx_res_checksum              55053
_shelx_hkl_checksum              78761