Conformational Control of Chiral Amido-Thiourea Catalysts Enables Improved Activity and Enantioselectivity.
Lehnherr, Dan; Ford, David D.; Bendelsmith, Andrew J.; Kennedy, C. Rose; Jacobsen, Eric N.; Organic letters 18 (2016) 3214–3217; doi:10.1021/acs.orglett.6b01435

data_1543792
_publ_section_title
;
 Conformational Control of Chiral Amido-Thiourea Catalysts Enables
 Improved Activity and Enantioselectivity.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3214
_journal_page_last               3217
_journal_paper_doi               10.1021/acs.orglett.6b01435
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C31 H41 Cl4 F7 N4 O2'
_chemical_formula_weight         776.48
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_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                   9.2304(8)
_cell_length_b                   13.9651(13)
_cell_length_c                   28.899(2)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.7
_cell_measurement_theta_min      3.05
_cell_volume                     3725.2(5)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_min       -15
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_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            53779
_diffrn_reflns_theta_full        66.85
_diffrn_reflns_theta_max         66.85
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    3.496
_exptl_absorpt_correction_T_max  0.7213
_exptl_absorpt_correction_T_min  0.5415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.381
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.015(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6368
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+1.8169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                5657
_reflns_number_total             6368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01435_si_002.cif
_cod_data_source_block           DLH-504A
_cod_original_cell_volume        3725.2(6)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1543792