Enantioselective monofluoromethylation of aldehydes with 2-fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide catalyzed by a bifunctional cinchona alkaloid-derived thiourea-titanium complex
Hai Ma; Kohei Matsuzaki; Yu-Dong Yang; Etsuko Tokunaga; Daisuke Nakane; Tomohiro Ozawa; Hideki Masuda; Norio Shibata; Chem.Commun. 49 (2013) 11206–; doi:10.1039/c3cc46544f

data_7110052
_publ_section_title
;
 Enantioselective monofluoromethylation of aldehydes with
 2-fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide catalyzed by a bifunctional
 cinchona alkaloid-derived thiourea-titanium complex
;
_journal_name_full               Chem.Commun.
_journal_page_first              11206
_journal_paper_doi               10.1039/c3cc46544f
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C21 H13 Br F N O8 S2'
_chemical_formula_sum            'C21 H13 Br F N O8 S2'
_chemical_formula_weight         570.36
_space_group_IT_number           4
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.288(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.3933(17)
_cell_length_b                   10.672(2)
_cell_length_c                   13.178(3)
_cell_measurement_reflns_used    3762
_cell_measurement_temperature    223
_cell_measurement_theta_max      31.20
_cell_measurement_theta_min      1.58
_cell_volume                     1157.6(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9001
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.017
_exptl_absorpt_correction_T_max  0.546
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             572.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         1.350
_refine_diff_density_min         -1.410
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2028 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.021(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4829
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.025
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0010Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                4319
_reflns_number_total             4829
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c3cc46544f.txt
_cod_data_source_block           MH-188-01
_cod_original_cell_volume        1157.5(4)
_cod_database_code               7110052