Enantioselective synthesis of monofluorinated allylic compounds: Pd-catalyzed asymmetric allylations of dimethyl 2-fluoromalonate using new N-sulfinyl-based ligands.
Gao, Ning; Zhao, Xiao-Ming; Cai, Cheng-Si; Cai, Jue-Wang; Organic & biomolecular chemistry 13 (2015) 9551–9558; doi:10.1039/c5ob01434d

data_7154631
_publ_section_title
;
 Enantioselective synthesis of monofluorinated allylic compounds:
 Pd-catalyzed asymmetric allylations of dimethyl 2-fluoromalonate using
 new N-sulfinyl-based ligands.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9551
_journal_page_last               9558
_journal_paper_doi               10.1039/c5ob01434d
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C14 H18 N2 O3 S'
_chemical_formula_weight         294.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-07-02 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.662(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.306(4)
_cell_length_b                   8.935(6)
_cell_length_c                   13.518(9)
_cell_measurement_reflns_used    774
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.448
_cell_measurement_theta_min      2.738
_cell_volume                     756.5(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3621
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         1.517
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
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_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       rod
_exptl_crystal_F_000             312
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_refine_diff_density_min         -0.210
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_refine_ls_abs_structure_details
; 
 Flack x determined using 720 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.13(9)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2992
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0583P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.735
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_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                2002
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_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           a31021a
_cod_depositor_comments
'Adding full bibliography for 7154631--7154632.cif.'
_cod_original_cell_volume        756.5(8)
_cod_database_code               7154631
_shelx_estimated_absorpt_t_min   0.920
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-2
_shelx_res_checksum              3855