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_1547020
_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         'C24 H29 Cl2 N O4'
_chemical_formula_sum            'C24 H29 Cl2 N O4'
_chemical_formula_weight         466.38
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4973)
;
_cell_angle_alpha                87.64(2)
_cell_angle_beta                 86.23(2)
_cell_angle_gamma                89.091(19)
_cell_formula_units_Z            2
_cell_length_a                   7.3804(17)
_cell_length_b                   9.680(2)
_cell_length_c                   16.898(4)
_cell_measurement_reflns_used    576
_cell_measurement_temperature    290.92(10)
_cell_measurement_theta_max      21.8070
_cell_measurement_theta_min      4.1530
_cell_volume                     1203.5(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      290.92(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -17.00   25.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.2008  -99.0000  -30.0000 35

  2 omega  -61.00    5.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.2008  -57.0000 -120.0000 55

  3 omega  -46.00   -6.40   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  -38.0000   30.0000 33

  4 omega   36.00   78.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  178.0000   60.0000 35

  5 omega   32.00   58.40   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  -99.0000 -150.0000 22

  6 omega  -36.00   39.60   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071  -57.0000   60.0000 63

  7 omega    2.00   92.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.1071   38.0000 -150.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0177437000
_diffrn_orient_matrix_UB_12      -0.0156854000
_diffrn_orient_matrix_UB_13      0.0411399000
_diffrn_orient_matrix_UB_21      -0.0515140000
_diffrn_orient_matrix_UB_22      -0.0575817000
_diffrn_orient_matrix_UB_23      -0.0090293000
_diffrn_orient_matrix_UB_31      0.0794316000
_diffrn_orient_matrix_UB_32      -0.0426618000
_diffrn_orient_matrix_UB_33      0.0000176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1162
_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            9676
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.135
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         9681
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1079P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1866
_refine_ls_wR_factor_ref         0.2182
_reflns_number_gt                3967
_reflns_number_total             9681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            zhang_1229_1_twin1_hklf4.cif
_cod_data_source_block           zhang_1229_1_twin1_hklf4
_cod_original_cell_volume        1203.6(5)
_cod_database_code               1547020
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9622(4) 0.0378(4)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C42) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C12(H12), C13(H13), C15(H15), C25(H25), C26(H26), C36(H36),
 C37(H37), C39(H39)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C18(H18A,H18B), C27(H27A,H27B), C28(H28A,H28B),
 C42(H42A,H42B)
4.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23), C45(H45), C46(H46), C47(H47)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C),
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C)
;
_olex2_submission_special_instructions 'No special instructions were received'