Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst.
Hurtley, Anna E.; Stone, Elizabeth A.; Metrano, Anthony J.; Miller, Scott J.; The Journal of organic chemistry 82 (2017) 11326–11336; doi:10.1021/acs.joc.7b02339

data_4033014
_publ_section_title
;
 Desymmetrization of Diarylmethylamido Bis(phenols) through
 Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2
 amu Alteration at an Achiral Residue within the Catalyst.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11326
_journal_page_last               11336
_journal_paper_doi               10.1021/acs.joc.7b02339
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C34 H34 Br N3 O5'
_chemical_formula_sum            'C34 H34 Br N3 O5'
_chemical_formula_weight         644.55
_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   geom
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_cell_angle_beta                 89.031(2)
_cell_angle_gamma                82.4628(19)
_cell_formula_units_Z            6
_cell_length_a                   11.4675(3)
_cell_length_b                   17.3110(4)
_cell_length_c                   23.6038(6)
_cell_measurement_reflns_used    60422
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.7510
_cell_measurement_theta_min      2.5680
_cell_volume                     4602.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41o (Rigaku OD, 2015)'
_computing_molecular_graphics
;
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            159288
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         1.889
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2004
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_refine_diff_density_max         4.489
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details
; 
 Flack x determined using 11896 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.016(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2365
_refine_ls_number_reflns         29946
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0654
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1251P)^2^+3.7203P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.867
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                28036
_reflns_number_total             29946
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02339_si_003.cif
_cod_data_source_block           007-16117
_cod_depositor_comments
'Adding full bibliography for 4033013--4033014.cif.'
_cod_original_cell_volume        4602.28(19)
_cod_database_code               4033014
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.667
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              94847
_shelx_hkl_checksum              1367