Modular Two-Step Approach for the Stereodivergent Synthesis of 1,3-Diamines with Three Continuous Stereocenters.
Halli, Juliette; Bolte, Michael; Bats, Jan; Manolikakes, Georg; Organic letters 19 (2017) 674–677; doi:10.1021/acs.orglett.6b03841

data_1556008
_publ_section_title
;
 Modular Two-Step Approach for the Stereodivergent Synthesis of
 1,3-Diamines with Three Continuous Stereocenters.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              674
_journal_page_last               677
_journal_paper_doi               10.1021/acs.orglett.6b03841
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H28 N2 O3 S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C29.5 H29 Cl N2 O3 S'
_chemical_formula_weight         527.06
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   18.4813(6)
_cell_length_b                   18.4813(6)
_cell_length_c                   16.4257(5)
_cell_measurement_reflns_used    46318
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.48
_cell_volume                     4858.7(3)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38699
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_min         2.529
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_description       block
_exptl_crystal_F_000             1662
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
; 
 Flack x determined using 2260 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.18(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         6316
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0655
_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^)+(0.1215P)^2^+0.6044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1751
_refine_ls_wR_factor_ref         0.1788
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                5830
_reflns_number_total             6316
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            8c.cif
_cod_data_source_block           ma71
_cod_original_formula_sum        'C29.50 H29 Cl N2 O3 S'
_cod_database_code               1556008
_shelx_shelxl_version_number     2014/7
_platon_squeeze_void_probe_radius 1.20
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.955
_shelx_res_checksum              42720
_shelx_hkl_checksum              48022
_shelx_fab_checksum              34847