Highly enantioselective metallation–substitution alpha to a chiral nitrile
Sadhukhan, Arghya; Hobbs, Melanie C.; Meijer, Anthony J. H. M.; Coldham, Iain; Chem. Sci. 8 (2017) 1436–; doi:10.1039/C6SC03712G

data_1544357
_publ_section_title
;
 Highly enantioselective metallation--substitution alpha to a chiral
 nitrile
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              1436
_journal_paper_doi               10.1039/C6SC03712G
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H21 Br N2 O3'
_chemical_formula_weight         393.28
_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   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-05-03 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.347(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8396(3)
_cell_length_b                   17.5572(7)
_cell_length_c                   11.6494(4)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.35
_cell_measurement_theta_min      4.56
_cell_volume                     1802.77(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.1401
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            44389
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         67.017
_diffrn_reflns_theta_min         3.805
_exptl_absorpt_coefficient_mu    3.259
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.757
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.163
_refine_ls_abs_structure_details
; 
 Flack x determined using 1484 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.040(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         44389
_refine_ls_number_restraints     261
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0825
_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^)+(0.1293P)^2^+0.2665P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2026
_refine_ls_wR_factor_ref         0.2326
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                31362
_reflns_number_total             44389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc03712g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1544357.cif.'
_cod_database_code               1544357
_shelx_estimated_absorpt_t_min   0.696
_shelx_estimated_absorpt_t_max   0.736
_shelxl_version_number           2014-1
_shelx_res_checksum              10801