Mapping the structural boundaries of quasiracemate fractional crystallization using 2-substituted diarylamides.
Tinsley, Ian C.; Spaniol, Jacqueline M.; Wheeler, Kraig A.; Chemical communications (Cambridge, England) 53 (2017) 4601–4604; doi:10.1039/c7cc01638g

data_7119928
_publ_section_title
;
 Mapping the structural boundaries of quasiracemate fractional
 crystallization using 2-substituted diarylamides.
;
_journal_issue                   33
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4601
_journal_page_last               4604
_journal_paper_doi               10.1039/c7cc01638g
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H14 N2 O3, C15 H13 Br N O'
_chemical_formula_sum            'C30 H28 Br N3 O4'
_chemical_formula_weight         574.46
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-02-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.342(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2953(5)
_cell_length_b                   9.5761(5)
_cell_length_c                   17.2423(9)
_cell_measurement_reflns_used    4629
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.27
_cell_measurement_theta_min      2.61
_cell_volume                     1342.92(13)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1097
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20609
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         2.614
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.420
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       'transparent plate'
_exptl_crystal_F_000             592
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1:1 hexanes:dichloromethane '
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.034
_refine_diff_density_max         1.047
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 1318 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(2)
_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     351
_refine_ls_number_reflns         4825
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0737
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+4.1799P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1652
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3810
_reflns_number_total             4825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc01638g2.cif
_cod_data_source_block           16kaw105
_cod_depositor_comments
'Adding full bibliography for 7119927--7119932.cif.'
_cod_database_code               7119928
_shelx_estimated_absorpt_t_min   0.716
_shelx_estimated_absorpt_t_max   0.922
_shelx_res_checksum              67374