Very short highly enantioselective Grignard synthesis of 2,2-disubstituted tetrahydrofurans and tetrahydropyrans.
Monasterolo, Claudio; Müller-Bunz, Helge; Gilheany, Declan G.; Chemical science 10 (2019) 6531–6538; doi:10.1039/c9sc00978g

data_1555232
_publ_section_title
;
 Very short highly enantioselective Grignard synthesis of
 2,2-disubstituted tetrahydrofurans and tetrahydropyrans.
;
_journal_issue                   26
_journal_name_full               'Chemical science'
_journal_page_first              6531
_journal_page_last               6538
_journal_paper_doi               10.1039/c9sc00978g
_journal_volume                  10
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 Br Cl N O2'
_chemical_formula_sum            'C19 H21 Br Cl N O2'
_chemical_formula_weight         410.73
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-12-04 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.143(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5181(2)
_cell_length_b                   11.3448(2)
_cell_length_c                   18.2344(4)
_cell_measurement_reflns_used    10744
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.7780
_cell_measurement_theta_min      4.6170
_cell_volume                     1900.60(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20680
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.106
_diffrn_reflns_theta_min         3.896
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.323
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
; 
 Flack x determined using 3506 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.012(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7823
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0685P)^2^+0.2945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                7668
_reflns_number_total             7823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00978g2.cif
_cod_data_source_block           gil104
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555232
_shelxl_version_number           2014-3
_shelx_res_checksum              31250