Temperature-Dependent Enantio- and Diastereodivergent Synthesis of Amino Acids with One or Multiple Chiral Centers.
Fan, Shiming; Liu, Shouxin; Zhu, Sufang; Feng, Juan; Zhang, Zhiwei; Huang, Jing; Organic letters 19 (2017) 4660–4663; doi:10.1021/acs.orglett.7b02296

data_1547023
_publ_section_title
;
 Temperature-Dependent Enantio- and Diastereodivergent Synthesis of Amino
 Acids with One or Multiple Chiral Centers.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4660
_journal_page_last               4663
_journal_paper_doi               10.1021/acs.orglett.7b02296
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H23 N O2'
_chemical_formula_sum            'C16 H23 N O2'
_chemical_formula_weight         261.35
_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   geom
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.8327(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.80751(15)
_cell_length_b                   6.84454(11)
_cell_length_c                   11.2630(2)
_cell_measurement_reflns_used    4889
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5600
_cell_measurement_theta_min      6.4370
_cell_volume                     727.38(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.964
_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   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  90.00  109
  2  \w     17.00 115.00   1.00    1.00    --   40.98  37.00  30.00   98
  3  \w    -33.00  65.00   1.00    1.00    --   40.98 -37.00  30.00   98
  4  \w      0.00 121.00   1.00    1.00    --   40.98  19.00-150.00  121
  5  \w     23.00  97.00   1.00    1.00    --   40.98-125.00   0.00   74
  6  \w     17.00 115.00   1.00    1.00    --   40.98  37.00  90.00   98
  7  \w     94.00 178.00   1.00    1.00    --  106.95 125.00-120.00   84
  8  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  30.00  104
  9  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00-120.00   85
 10  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 150.00   97
 11  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  30.00   97
 12  \w     78.00 178.00   1.00    1.00    --  106.95  61.00   0.00  100
 13  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00  30.00   85
 14  \w     74.00 153.00   1.00    1.00    --  106.95  77.00 120.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1519375000
_diffrn_orient_matrix_UB_12      0.0209788000
_diffrn_orient_matrix_UB_13      0.0123636000
_diffrn_orient_matrix_UB_21      0.0597995000
_diffrn_orient_matrix_UB_22      0.0534410000
_diffrn_orient_matrix_UB_23      0.1372741000
_diffrn_orient_matrix_UB_31      0.0001679000
_diffrn_orient_matrix_UB_32      0.2176346000
_diffrn_orient_matrix_UB_33      -0.0347897000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5602
_diffrn_reflns_point_group_measured_fraction_full 0.875
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.707
_diffrn_reflns_theta_min         4.080
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 905 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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2465
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0412P)^2^+0.1096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.604
_reflns_Friedel_fraction_full    0.743
_reflns_Friedel_fraction_max     0.694
_reflns_number_gt                2436
_reflns_number_total             2465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            shang-40_2.cif
_cod_data_source_block           shang-40_2
_cod_database_code               1547023
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.882
_reflns_odcompleteness_completeness 98.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C2(H2), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C16(H16A,H16B,H16C),
 C15(H15A,H15B,H15C)
;
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.622