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_1566033
_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         'C25 H28 N O6 S'
_chemical_formula_sum            'C25 H28 N O6 S'
_chemical_formula_weight         470.54
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc28wd1m
_audit_creation_date             2021-09-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-24 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.0474(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.34486(14)
_cell_length_b                   10.19459(12)
_cell_length_c                   12.07537(18)
_cell_measurement_reflns_used    12767
_cell_measurement_temperature    303.37(10)
_cell_measurement_theta_max      76.0300
_cell_measurement_theta_min      3.7840
_cell_volume                     1229.82(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.37(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_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     39.00 117.00   0.50    0.05    --   46.32  57.00 120.00  156
  2  \w     38.00 117.00   0.50    0.05    --   46.32  38.00  46.00  158
  3  \w     27.00  69.00   0.50    0.05    --   46.32  77.00-180.00   84
  4  \w     34.00 118.00   0.50    0.05    --   46.32  37.00-150.00  168
  5  \w     83.00 170.00   0.50    0.10    --  104.25 125.00-180.00  174
  6  \w     39.00  99.00   0.50    0.10    --  104.25 -94.00  90.00  120
  7  \w    -21.00  27.00   0.50    0.05    --   46.32 -19.00  90.00   96
  8  \w    -23.00   4.00   0.50    0.05    --   46.32 -38.00-108.00   54
  9  \w     42.00  98.00   0.50    0.10    --  104.25 -94.00 -30.00  112
 10  \w     59.00  84.00   0.50    0.10    --  104.25 -77.00 -60.00   50
 11  \w     97.00 170.00   0.50    0.10    --  104.25  15.00  30.00  146
 12  \w     83.00 109.00   0.50    0.10    --  104.25  77.00 150.00   52
 13  \w     91.00 145.00   0.50    0.10    --  104.25  38.00  46.00  108
 14  \w    135.00 177.00   0.50    0.10    --  104.25  15.00 -60.00   84
 15  \w     88.00 114.00   0.50    0.10    --  104.25  61.00-180.00   52
 16  \w    -65.00 -35.00   0.50    0.05    --  -46.32 -37.00-180.00   60
 17  \w    -94.00 -50.00   0.50    0.05    --  -46.32 -38.00-108.00   88
 18  \w    -73.00 -48.00   0.50    0.10    -- -102.00 125.00  90.00   50
 19  \w   -112.00 -77.00   0.50    0.10    -- -102.00 125.00  90.00   70
 20  \w    -99.00 -40.00   0.50    0.10    -- -102.00  77.00 -60.00  118
 21  \w    -62.00 -29.00   0.50    0.10    -- -102.00  61.00 -90.00   66
 22  \w    -57.00 -31.00   0.50    0.10    -- -102.00  61.00-150.00   52
 23  \w    -69.00 -29.00   0.50    0.10    -- -102.00  61.00-180.00   80
 24  \w    -31.00  -6.00   0.50    0.05    --  -46.32  38.00  46.00   50
 25  \w    -65.00 -39.00   0.50    0.10    -- -102.00  61.00 150.00   52
 26  \w    -69.00 -32.00   0.50    0.10    -- -102.00  61.00  60.00   74
 27  \w   -132.00-107.00   0.50    0.10    -- -102.00 -38.00-108.00   50
 28  \w   -106.00 -81.00   0.50    0.10    -- -102.00 -78.00-160.31   50
 29  \w   -117.00 -79.00   0.50    0.10    -- -102.00 -77.00-150.00   76
 30  \w   -106.00 -80.00   0.50    0.10    -- -102.00 -77.00-180.00   52
 31  \w   -174.00-121.00   0.50    0.10    -- -102.00 -78.00-160.31  106
 32  \w   -105.00 -80.00   0.50    0.10    -- -102.00 -74.00-171.06   50
 33  \w   -164.00 -79.00   0.50    0.10    -- -102.00 -77.00 120.00  170
 34  \w   -106.00 -81.00   0.50    0.10    -- -102.00 -74.00 129.34   50
 35  \w   -104.00 -79.00   0.50    0.10    -- -102.00 -77.00 150.00   50
 36  \w   -107.00 -81.00   0.50    0.10    -- -102.00 -72.00 148.74   52
 37  \w   -105.00 -80.00   0.50    0.10    -- -102.00 -74.00 167.91   50
 38  \w   -110.00 -85.00   0.50    0.10    -- -102.00 -62.00 125.46   50
 39  \w   -109.00 -84.00   0.50    0.10    -- -102.00 -69.00 151.29   50
 40  \w   -175.00-128.00   0.50    0.10    -- -102.00 -77.00 150.00   94
 41  \w   -174.00 -88.00   0.50    0.10    -- -102.00 -57.00 161.71  172
 42  \w   -134.00 -88.00   0.50    0.10    -- -102.00 -61.00 120.00   92
 43  \w   -170.00-144.00   0.50    0.10    -- -102.00 -45.00 178.95   52
 44  \w   -142.00 -89.00   0.50    0.10    -- -102.00 -45.00 178.95  106
 45  \w   -143.00-118.00   0.50    0.10    -- -102.00 -55.00 103.80   50
 46  \w   -171.00 -87.00   0.50    0.10    -- -102.00 -61.00-150.00  168
 47  \w   -107.00 -82.00   0.50    0.10    -- -102.00 -69.00-168.00   50
 48  \w   -114.00 -89.00   0.50    0.10    -- -102.00 -45.00-150.00   50
 49  \w   -119.00 -75.00   0.50    0.05    --  -46.32-125.00  60.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0998795000
_diffrn_orient_matrix_UB_12      0.0628183000
_diffrn_orient_matrix_UB_13      -0.0592542000
_diffrn_orient_matrix_UB_21      0.1166018000
_diffrn_orient_matrix_UB_22      -0.0376465000
_diffrn_orient_matrix_UB_23      0.1031398000
_diffrn_orient_matrix_UB_31      0.0142015000
_diffrn_orient_matrix_UB_32      -0.1322015000
_diffrn_orient_matrix_UB_33      -0.0575011000
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18191
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.245
_diffrn_reflns_theta_min         3.791
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1885 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.043(15)
_refine_ls_extinction_coef       0.0053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4877
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0540P)^2^+0.1072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                4501
_reflns_number_total             4877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06127e2.cif
_cod_data_source_block           jidongs-0923-1_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1566033
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 100.00
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{S1, C1'}
{C25, S1'}
3. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(C1')
Uanis(C25) = Uanis(S1')
4. Others
 Fixed Sof: S1(0.5) C25(0.5) H2A(0.5) H2B(0.5) H1A(0.5) H1B(0.5) S1'(0.5)
 C1'(0.5)
5.a Ternary CH refined with riding coordinates:
 C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C18(H18A,H18B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C2(H2B), C1(H1A), C1(H1B), C14(H14), C12(H12), C13(H13),
 C16(H16), C15(H15)
5.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C7(H7A,H7B,H7C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              55198
_shelx_hkl_checksum              3473
_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.708