Chiral Aldehyde Catalysis for the Catalytic Asymmetric Activation of Glycine Esters.
Wen, Wei; Chen, Lei; Luo, Ming-Jing; Zhang, Yan; Chen, Ying-Chun; Ouyang, Qin; Guo, Qi-Xiang; Journal of the American Chemical Society 140 (2018) 9774–9780; doi:10.1021/jacs.8b06676

data_4132802
_publ_section_title
;
 Chiral Aldehyde Catalysis for the Catalytic Asymmetric Activation of
 Glycine Esters.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9774
_journal_page_last               9780
_journal_paper_doi               10.1021/jacs.8b06676
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C27 H17 Br O2'
_chemical_formula_sum            'C27 H17 Br O2'
_chemical_formula_weight         453.32
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.8127(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.66779(16)
_cell_length_b                   13.8650(2)
_cell_length_c                   13.5618(2)
_cell_measurement_reflns_used    26081
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.0280
_cell_measurement_theta_min      4.1210
_cell_volume                     1998.84(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -104.00 -20.00   1.00    1.00    --  -37.16 -57.00 -90.00   84
  2  \w   -109.00  -8.00   1.00    1.00    --  -37.16 -19.00  30.00  101
  3  \w   -105.00 -10.00   1.00    1.00    --  -37.16 -77.00-180.00   95
  4  \w    -91.00  -3.00   1.00    1.00    --  -37.16 126.00 -60.00   88
  5  \w    -71.00  32.00   1.00    1.00    --  -37.16  90.00 -91.00  103
  6  \w    -30.00  54.00   1.00    1.00    --   37.16 -57.00  30.00   84
  7  \w    -30.00  54.00   1.00    1.00    --   37.16 -57.00 -60.00   84
  8  \w     24.00  91.00   1.00    1.00    --   37.16-126.00-150.00   67
  9  \w     24.00  91.00   1.00    1.00    --   37.16-126.00 120.00   67
 10  \w     24.00  91.00   1.00    1.00    --   37.16-126.00 -90.00   67
 11  \w    -30.00  54.00   1.00    1.00    --   37.16 -57.00 -30.00   84
 12  \w    -34.00  67.00   1.00    1.00    --   37.16 -19.00  60.00  101
 13  \w      1.00  76.00   1.00    1.00    --   37.16 -99.00  60.00   75
 14  \w    -32.00  56.00   1.00    1.00    --   37.16 -38.00-180.00   88
 15  \w      8.00 109.00   1.00    1.00    --   37.16  19.00 -30.00  101
 16  \w     24.00  91.00   1.00    1.00    --   37.16-126.00 150.00   67
 17  \w    101.00 178.00   1.00    1.00    --  110.47 112.00  30.00   77
 18  \w     43.00 137.00   1.00    1.00    --  110.47 -77.00  60.00   94
 19  \w     72.00 178.00   1.00    1.00    --  110.47  15.00  60.00  106
 20  \w     41.00 116.00   1.00    1.00    --  110.47-112.00-120.00   75
 21  \w     41.00 116.00   1.00    1.00    --  110.47-112.00  90.00   75
 22  \w     41.00 109.00   1.00    1.00    --  110.47 -95.00   0.00   68
 23  \w     41.00 109.00   1.00    1.00    --  110.47 -95.00 -30.00   68
 24  \w    101.00 178.00   1.00    1.00    --  110.47 112.00-120.00   77
 25  \w     42.00 128.00   1.00    1.00    --  110.47 -45.00  30.00   86
 26  \w     89.00 178.00   1.00    1.00    --  110.47  30.00 -30.00   89
 27  \w     44.00 129.00   1.00    1.00    --  110.47 -61.00-150.00   85
 28  \w     41.00 132.00   1.00    1.00    --  110.47 -30.00-150.00   91
 29  \w     43.00 137.00   1.00    1.00    --  110.47 -77.00 120.00   94
 30  \w     41.00 132.00   1.00    1.00    --  110.47 -30.00 120.00   91
 31  \w     42.00 128.00   1.00    1.00    --  110.47 -45.00 -60.00   86
 32  \w    101.00 178.00   1.00    1.00    --  110.47 112.00-150.00   77
 33  \w     93.00 178.00   1.00    1.00    --  110.47  45.00 -60.00   85
 34  \w   -104.00 -20.00   1.00    1.00    --  -37.16 -57.00-150.00   84
 35  \w    -67.00  34.00   1.00    1.00    --  -37.16  19.00   0.00  101
 36  \w   -105.00 -10.00   1.00    1.00    --  -37.16 -77.00  90.00   95
 37  \w   -105.00 -10.00   1.00    1.00    --  -37.16 -77.00 150.00   95
 38  \w    -54.00  30.00   1.00    1.00    --  -37.16  57.00  60.00   84
 39  \w   -104.00 -20.00   1.00    1.00    --  -37.16 -57.00  60.00   84
 40  \w   -105.00 -10.00   1.00    1.00    --  -37.16 -77.00   0.00   95
 41  \w   -104.00 -20.00   1.00    1.00    --  -37.16 -57.00   0.00   84
 42  \w   -106.00 -18.00   1.00    1.00    --  -37.16 -38.00-150.00   88
 43  \w   -104.00 -20.00   1.00    1.00    --  -37.16 -57.00-180.00   84
 44  \w   -106.00 -18.00   1.00    1.00    --  -37.16 -38.00   0.00   88
 45  \w   -105.00 -10.00   1.00    1.00    --  -37.16 -77.00-120.00   95
 46  \w    -32.00 106.00   1.00    1.00    --   37.16   0.00 120.00  138
 47  \w     10.00 105.00   1.00    1.00    --   37.16  77.00 -30.00   95
 48  \w     20.00 104.00   1.00    1.00    --   37.16  57.00-150.00   84
 49  \w     10.00 105.00   1.00    1.00    --   37.16  77.00   0.00   95
 50  \w     72.00 155.00   1.00    1.00    --  110.47  15.00 150.00   83
 51  \w     72.00 178.00   1.00    1.00    --  110.47  15.00-120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0376891000
_diffrn_orient_matrix_UB_12      0.0878782000
_diffrn_orient_matrix_UB_13      0.0604783000
_diffrn_orient_matrix_UB_21      0.1241395000
_diffrn_orient_matrix_UB_22      0.0504109000
_diffrn_orient_matrix_UB_23      -0.0197226000
_diffrn_orient_matrix_UB_31      -0.0645046000
_diffrn_orient_matrix_UB_32      0.0455565000
_diffrn_orient_matrix_UB_33      -0.0946644000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1298
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33201
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.043
_diffrn_reflns_theta_min         4.159
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.355
_refine_diff_density_min         -1.389
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
;
 Flack x determined using 3211 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(14)
_refine_ls_extinction_coef       0.0014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         7758
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0666
_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^)+(0.1330P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1755
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                7487
_reflns_number_total             7758
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b06676_si_003.cif
_cod_data_source_block           gqx-09-13
_cod_original_cell_volume        1998.85(6)
_cod_database_code               4132802
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C1 H1 O1 Br1'
_shelx_estimated_absorpt_t_max   0.574
_shelx_estimated_absorpt_t_min   0.342
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C37(H37), C38(H38),
 C39(H39), C40(H40), C42(H42), C43(H43), C46(H46), C47(H47), C48(H48), C49(H49),
  C54(H54)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.071
_oxdiff_exptl_absorpt_empirical_full_min 0.199