Solvent Directed Chemical Divergent Synthesis of β-Lactams and α-Amino Acid Derivatives with Chiral Isothiourea
Ji, Dong-Sheng; Liang, Hui; Yang, Kai-Xuan; Feng, Zhitao; Luo, Yong-Chun; Xu, Guo-Qiang; Gu, Yucheng; Xu, Peng-Fei; Chemical Science  (2022) –; doi:10.1039/D1SC06127E

data_1566034
_publ_section_title
;
 Solvent Directed Chemical Divergent Synthesis of \b-Lactams and \a-Amino
 Acid Derivatives with Chiral Isothiourea
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06127E
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H27 N O5'
_chemical_formula_sum            'C26 H27 N O5'
_chemical_formula_weight         433.48
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2021-04-15 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3138(4)
_cell_length_b                   11.6736(5)
_cell_length_c                   25.1152(10)
_cell_measurement_reflns_used    1870
_cell_measurement_temperature    291.90(10)
_cell_measurement_theta_max      68.0160
_cell_measurement_theta_min      9.9180
_cell_volume                     2437.48(18)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.90(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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     23.00  56.00   1.00    1.00    --   54.00-125.00  30.00   33
  2  \w     75.00 102.00   1.00    1.00    --  108.00 -63.00  60.00   27
  3  \w     96.00 129.00   1.00    1.00    --  108.00 -38.00 -30.00   33
  4  \w     63.00  91.00   1.00    1.00    --  108.00 -38.00 -30.00   28
  5  \w     36.00 113.00   1.00    1.00    --  108.00-111.00-120.00   77
  6  \w     24.00 101.00   1.00    1.00    --   54.00-125.00 -90.00   77
  7  \w     32.00  70.00   1.00    1.00    --    0.00  38.00  90.00   38
  8  \w     10.00  73.00   1.00    1.00    --   54.00   0.00 150.00   63
  9  \w     87.00 173.00   1.00    1.00    --  108.00  63.00 120.00   86
 10  \w    119.00 156.00   1.00    1.00    --  108.00 111.00 150.00   37
 11  \w    102.00 128.00   1.00    1.00    --  108.00 111.00  60.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0227801000
_diffrn_orient_matrix_UB_12      0.0893406000
_diffrn_orient_matrix_UB_13      -0.0445285000
_diffrn_orient_matrix_UB_21      -0.1837519000
_diffrn_orient_matrix_UB_22      0.0136508000
_diffrn_orient_matrix_UB_23      -0.0044142000
_diffrn_orient_matrix_UB_31      0.0049286000
_diffrn_orient_matrix_UB_32      0.0962473000
_diffrn_orient_matrix_UB_33      0.0419533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5596
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        66.572
_diffrn_reflns_theta_max         66.572
_diffrn_reflns_theta_min         5.605
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75579
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'volatilize solvent in NMR tube( CDCl3)'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 1013 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(16)
_refine_ls_extinction_coef       0.0082(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0433P)^2^+0.1827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_full    0.744
_reflns_Friedel_fraction_max     0.744
_reflns_number_gt                3210
_reflns_number_total             3804
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06127e2.cif
_cod_data_source_block           jidsh_0706
_cod_original_cell_volume        2437.47(18)
_cod_database_code               1566034
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.913
_reflns_odcompleteness_completeness 98.81
_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. Others
 Fixed Sof: C26(0.5) H26A(0.5) H26B(0.5) H26C(0.5) C25(0.5) H25A(0.5)
 H25B(0.5) C25B(0.5) H25C(0.5) H25D(0.5) C26B(0.5) H26D(0.5) H26E(0.5) H26F(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C25B(H25C,H25D)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C10(H10), C15(H15), C9(H9), C8(H8), C13(H13), C11(H11), C14(H14),
 C7(H7)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C), C26(H26A,H26B,H26C), C26B(H26D,H26E,H26F)
;
_shelx_res_checksum              17673
_shelx_hkl_checksum              45279
_olex2_date_sample_data_collection 2020-07-08
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.762