Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of Unprotected Unnatural Tailor-made α-Amino Acids.
Wang, Shuni; Zhou, Shengbin; Wang, Jiang; Nian, Yong; Kawashima, Aki; Moriwaki, Hiroki; Aceña, José L; Soloshonok, Vadim A.; Liu, Hong; The Journal of organic chemistry 80 (2015) 9817–9830; doi:10.1021/acs.joc.5b01292

data_4036259
_publ_section_title
;
 Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of
 Unprotected Unnatural Tailor-made \a-Amino Acids.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9817
_journal_page_last               9830
_journal_paper_doi               10.1021/acs.joc.5b01292
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C46 H33 Cl2 N3 Ni O3, 0.5(C H4 O), H2 O'
_chemical_formula_sum            'C46.5 H37 Cl2 N3 Ni O4.5'
_chemical_formula_weight         839.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1326(13)
_cell_length_b                   19.4409(15)
_cell_length_c                   26.943(2)
_cell_measurement_reflns_used    3977
_cell_measurement_temperature    130
_cell_measurement_theta_max      23.63
_cell_measurement_theta_min      2.23
_cell_volume                     8450.2(11)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1640
_diffrn_reflns_av_unetI/netI     0.1830
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            76830
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.788
_diffrn_reflns_theta_min         1.512
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0811 before and 0.0703 after correction.
The Ratio of minimum to maximum transmission is 0.8831.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             3480
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 3428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1029
_refine_ls_number_reflns         21977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.1511
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0640P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                10654
_reflns_number_total             21977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01292_si_001.cif
_cod_data_source_block           mo_dm14494_0m
_cod_depositor_comments
;

2020-07-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C93 H74 Cl4 N6 Ni2 O9'
_cod_original_formula_weight         1678.80
_cod_original_formula_moiety         '2(C46 H33 Cl2 N3 Ni O3), C H4 O, 2(H2 O)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        8450.1(12)
_cod_database_code               4036259
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.928
_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, All O(H,H) groups
2.a Riding coordinates:
 O2S(H2SA,H2SB), O3S(H3SA,H3SB)
2.b Ternary CH refined with riding coordinates:
 C38(H38), C38A(H38A)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C22(H22A,H22B), C23(H23A,H23B), C40(H40A,H40B), C1A(H1AA,H1AB),
 C22A(H22C,H22D), C23A(H23C,H23D), C40A(H40C,H40D)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C26(H26), C27(H27), C29(H29), C33(H33), C34(H34),
  C35(H35), C36(H36), C37(H37), C42(H42), C43(H43), C45(H45), C46(H46),
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C19A(H19A), C20A(H20A), C26A(H26A),
 C27A(H27A), C29A(H29A), C33A(H33A), C34A(H34A), C35A(H35A), C36A(H36A),
 C37A(H37A), C42A(H42A), C43A(H43A), C45A(H45A), C46A(H46A)
2.e Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
2.f Idealised tetrahedral OH refined as rotating group:
 O1S(H1S)
;
_shelx_res_checksum              11053
_shelx_hkl_checksum              84714
_olex2_submission_special_instructions 'No special instructions were received'