Halide-Mediated <i>Ortho</i>-Deprotonation Reactions Applied to the Synthesis of 1,2- and 1,3-Disubstituted Ferrocene Derivatives.
Zirakzadeh, Afrooz; Herlein, Alexander; Groß, Manuela A; Mereiter, Kurt; Wang, Yaping; Weissensteiner, Walter; Organometallics 34 (2015) 3820–3832; doi:10.1021/acs.organomet.5b00464

data_4087651
_publ_section_title
;
 Halide-Mediated <i>Ortho</i>-Deprotonation Reactions Applied to the
 Synthesis of 1,2- and 1,3-Disubstituted Ferrocene Derivatives.
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              3820
_journal_page_last               3832
_journal_paper_doi               10.1021/acs.organomet.5b00464
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C10 H7 Br Fe I2'
_chemical_formula_sum            'C10 H7 Br Fe I2'
_chemical_formula_weight         516.72
_chemical_name_common            '1734 2-Bromo-1,3-diiodoferrocene at 100K'
_chemical_name_systematic
; 
2-Bromo-1,3-diiodoferrocene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 98.7370(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0176(3)
_cell_length_b                   16.0517(7)
_cell_length_c                   10.6927(5)
_cell_measurement_reflns_used    9792
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.31
_cell_volume                     1190.50(9)
_computing_cell_refinement       'Bruker SAINT V8.34A'
_computing_data_collection       'Bruker APEX2 V2014'
_computing_data_reduction        'Bruker SAINT V8.34A'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31435
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_min         2.307
_diffrn_source                   'fine focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    9.767
_exptl_absorpt_correction_T_max  0.49
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS-2014/4'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.883
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       0.00104(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.231
_refine_ls_R_factor_all          0.0158
_refine_ls_R_factor_gt           0.0151
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0035P)^2^+1.8266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0302
_refine_ls_wR_factor_ref         0.0304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3384
_reflns_number_total             3466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00464_si_002.cif
_cod_data_source_block           1734comp9
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4087651
_shelxl_version_number           2014/6
_shelx_res_checksum              24329
_shelx_hkl_checksum              5092