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_1547024
_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 H25 N O3'
_chemical_formula_sum            'C16 H25 N O3'
_chemical_formula_weight         279.37
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                99.194(3)
_cell_angle_beta                 98.907(3)
_cell_angle_gamma                102.923(2)
_cell_formula_units_Z            4
_cell_length_a                   10.9576(3)
_cell_length_b                   10.9859(3)
_cell_length_c                   13.5339(5)
_cell_measurement_reflns_used    11611
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.4370
_cell_measurement_theta_min      4.2100
_cell_volume                     1536.48(9)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.958
_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    -96.00  -2.00   1.00    1.00    --  -40.73 125.00 -90.00   94
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -37.00  30.00   99
  3  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -37.00 120.00   99
  4  \w    -65.00  34.00   1.00    1.00    --  -40.73  37.00  90.00   99
  5  \w      1.00  82.00   1.00    1.00    --   40.73 -99.00 -90.00   81
  6  \w     16.00 115.00   1.00    1.00    --   40.73  37.00-150.00   99
  7  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00   0.00   99
  8  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00 150.00   99
  9  \w     79.00 178.00   1.00    1.00    --  106.95  30.00 150.00   99
 10  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 150.00   84
 11  \w     34.00 121.00   1.00    1.00    --  106.95-125.00 120.00   87
 12  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00-180.00   85
 13  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 -30.00   97
 14  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00 -90.00   85
 15  \w     81.00 178.00   1.00    1.00    --  106.95  45.00-180.00   97
 16  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  60.00   84
 17  \w     29.00 114.00   1.00    1.00    --  106.95-106.00 -25.00   85
 18  \w     94.00 178.00   1.00    1.00    --  106.95 125.00-150.00   84
 19  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 -90.00   84
;
_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      -0.0427561000
_diffrn_orient_matrix_UB_12      0.1144621000
_diffrn_orient_matrix_UB_13      -0.0326772000
_diffrn_orient_matrix_UB_21      -0.0443199000
_diffrn_orient_matrix_UB_22      0.0289567000
_diffrn_orient_matrix_UB_23      0.1018533000
_diffrn_orient_matrix_UB_31      0.1336563000
_diffrn_orient_matrix_UB_32      0.0874103000
_diffrn_orient_matrix_UB_33      0.0489673000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15219
_diffrn_reflns_point_group_measured_fraction_full 0.660
_diffrn_reflns_point_group_measured_fraction_max 0.637
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.575
_diffrn_reflns_theta_min         4.216
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79546
_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    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.077
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 1870 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     745
_refine_ls_number_reflns         7909
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0683
_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^)+(0.1340P)^2^+0.5907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1736
_reflns_Friedel_coverage         0.330
_reflns_Friedel_fraction_full    0.337
_reflns_Friedel_fraction_max     0.316
_reflns_number_gt                7804
_reflns_number_total             7909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            xia-40_2.cif
_cod_data_source_block           xia-40_2
_cod_original_cell_volume        1536.48(8)
_cod_database_code               1547024
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.868
_reflns_odcompleteness_completeness 98.40
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00N(H00N), C14(H14), C00Q(H00Q), C13(H13), C00V(H00V), C00W(H00W), C6(H6),
 C00Z(H00Z), C2(H2), C012(H012), C015(H015), C018(H018), C019(H019), C01A(H01),
 C01E(H0AA), C01G(H1AA), C12(H12), C01J(H01M), C01K(H2AA), C01N(H01N)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C00T(H00D,H00E), C00U(H00I,H00J), C00X(H00F,H00G), C3(H3A,H3B),
 C01O(H4AA,HD), C01R(H01O,H01P), C024(H02D,H02E)
2.c Idealised Me refined as rotating group:
 C00J(H00A,H00B,H00C), C10(H10A,H10B,H10C), C013(H01Z,H,HA), C017(H01J,H01K,
 H01L), C01C(H01A,H01B,H01C), C01I(H01D,H01E,H01F), C01L(H3AA,HB,HC), C8(H8A,
 H8B,H8C), C9(H9A,H9B,H9C), C01Q(H5AA,HE,HF), C01U(H01Q,H01R,H01S), C01X(H01T,
 H01U,H01V), C01Y(H01G,H01H,H01I), C01Z(H01W,H01X,H01Y), C15(H15A,H15B,H15C),
 C022(H02A,H02B,H02C), C025(H02I,H02J,H02K), C026(H02L,H02M,H02N), C16(H16A,
 H16B,H16C), C028(H02F,H02G,H02H)
2.d Idealised tetrahedral OH refined as rotating group:
 O006(H006), O008(H008), O3(H3), O00B(H00H)
;
_olex2_date_sample_data_collection 2017-04-10
_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 2.308
_oxdiff_exptl_absorpt_empirical_full_min 0.687