Synthesis of both enantiomers of ferrocene[1,2-c]1H-quinolin-2-one by diastereoselective deproto-zincation of sugar-derived ferrocene esters
Sreeshailam, Aare; Dayaker, Gandrath; Ramana, D. Venkata; Chevallier, Floris; Roisnel, Thierry; Komagawa, Shinsuke; Takita, Ryo; Uchiyama, Masanobu; Krishna, Palakodety Radha; Mongin, Florence; RSC Advances 2 (2012) 7030–; doi:10.1039/c2ra21045b

data_7238689
_publ_section_title
;
 Synthesis of both enantiomers of ferrocene[1,2-c]1H-quinolin-2-one by
 diastereoselective deproto-zincation of sugar-derived ferrocene esters
;
_journal_issue                   18
_journal_name_full               'RSC Advances'
_journal_page_first              7030
_journal_paper_doi               10.1039/c2ra21045b
_journal_volume                  2
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         '2(C23 H28 Fe O7)'
_chemical_formula_sum            'C46 H56 Fe2 O14'
_chemical_formula_weight         944.61
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-01-07T16:41:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.150(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1999(4)
_cell_length_b                   12.2306(4)
_cell_length_c                   16.1208(6)
_cell_measurement_reflns_used    6202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.55
_cell_measurement_wavelength     0.71073
_cell_volume                     2191.08(13)
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18746
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.731
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         9694
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0180P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.055
_refine_ls_wR_factor_ref         0.0562
_reflns_number_gt                9093
_reflns_number_total             9694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra21045b.txt
_cod_data_source_block           2f
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7238689