Calcium(ii)-catalyzed enantioselective conjugate additions of amines.
Uno, Brice E.; Dicken, Rachel D.; Redfern, Louis R.; Stern, Charlotte M.; Krzywicki, Greg G.; Scheidt, Karl A.; Chemical science 9 (2018) 1634–1639; doi:10.1039/c7sc05205g

data_1548657
_publ_section_title
;
 Calcium(ii)-catalyzed enantioselective conjugate additions of amines.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1634
_journal_page_last               1639
_journal_paper_doi               10.1039/c7sc05205g
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H17 Br N2 O2'
_chemical_formula_sum            'C18 H17 Br N2 O2'
_chemical_formula_weight         373.24
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-19
_audit_creation_method
;
Olex2 1.2
(compiled Nov  7 2016 13:22:42 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-02-06 deposited with the CCDC.
2017-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                100.603(8)
_cell_angle_beta                 92.652(8)
_cell_angle_gamma                94.550(9)
_cell_formula_units_Z            1
_cell_length_a                   4.6810(5)
_cell_length_b                   6.1091(7)
_cell_length_c                   14.2048(16)
_cell_measurement_reflns_used    2766
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.66
_cell_measurement_theta_min      3.17
_cell_volume                     397.25(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_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_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4192
_diffrn_reflns_point_group_measured_fraction_full 0.848
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        66.660
_diffrn_reflns_theta_max         66.660
_diffrn_reflns_theta_min         3.171
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.621
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1108 before and 0.0459 after correction.
The Ratio of minimum to maximum transmission is 0.7685.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             190
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 965 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2403
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0531P)^2^+1.4835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.753
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                2336
_reflns_number_total             2403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc05205g2.cif
_cod_data_source_block           xrd0843
_cod_depositor_comments
'Adding full bibliography for 1548656--1548657.cif.'
_cod_database_code               1548657
_shelx_estimated_absorpt_t_max   0.763
_shelx_estimated_absorpt_t_min   0.641
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H11A,H11B), C12(H15A,H15B), C7(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H6), C15(H8), C18(H10), C14(H12), C17(H14), C3(H16), C1(H17), C5(H18),
 C2(H20)
;
_shelx_res_checksum              19987
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'