Modular Synthesis of 1,2- and 1,1′-Disubstituted Ferrocenyl Carbohydrate Chloroquine and Mefloquine Conjugates as Potential Antimalarial Agents
Herrmann, Christoph; Salas, Paloma F.; Patrick, Brian O.; Kock, Carmen de; Smith, Peter J.; Adam, Michael J.; Orvig, Chris; Organometallics 31 (2012) 5748–; doi:10.1021/om300392q

data_4078753
_publ_section_title
;
 Modular Synthesis of 1,2- and 1,1&#x2032;-Disubstituted Ferrocenyl
 Carbohydrate Chloroquine and Mefloquine Conjugates as Potential
 Antimalarial Agents
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              5748
_journal_paper_doi               10.1021/om300392q
_journal_volume                  31
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H13 F6 Fe N O2'
_chemical_formula_weight         493.18
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8812(7)
_cell_length_b                   10.6659(10)
_cell_length_c                   23.064(2)
_cell_measurement_reflns_used    9825
_cell_measurement_temperature    90.0(1)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.58
_cell_volume                     1938.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            31669
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.017(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.3166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                5155
_reflns_number_total             5665
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            om300392q_si_002.cif
_cod_data_source_block           co385
_cod_depositor_comments
'Adding full bibliography for 4078752--4078756.cif.'
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               4078753