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_1566035
_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_formula_moiety         'C26 H27 N O5'
_chemical_formula_sum            'C26 H27 N O5'
_chemical_formula_weight         433.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2021-10-27 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                97.5000(9)
_cell_angle_beta                 93.5092(9)
_cell_angle_gamma                110.6596(12)
_cell_formula_units_Z            2
_cell_length_a                   8.76363(11)
_cell_length_b                   11.32074(14)
_cell_length_c                   13.30299(13)
_cell_measurement_reflns_used    24192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2280
_cell_measurement_theta_min      3.3710
_cell_volume                     1216.15(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_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_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     31.00  57.00   0.50    0.07    --   50.00  74.00 -52.58   52
  2  \w     37.00  79.00   0.50    0.07    --   50.00  74.00 -91.74   84
  3  \w     28.00  54.00   0.50    0.07    --   46.32  77.00  60.00   52
  4  \w     31.00  57.00   0.50    0.07    --   50.00  74.00  90.06   52
  5  \w     66.00  92.00   0.50    0.07    --   46.32  19.00  60.00   52
  6  \w     48.00  73.00   0.50    0.12    --  104.25 -94.00-180.00   50
  7  \w     47.00  77.00   0.50    0.12    --  104.25-120.00-120.00   60
  8  \w     48.00  73.00   0.50    0.07    --   46.32-153.00  80.00   50
  9  \w     53.00 112.00   0.50    0.12    --  104.25-125.00 150.00  118
 10  \w     61.00 112.00   0.50    0.12    --  104.25-125.00 120.00  102
 11  \w     82.00 107.00   0.50    0.12    --  104.25-153.00  80.00   50
 12  \w     29.00  55.00   0.50    0.07    --   46.32-120.00-120.00   52
 13  \w     50.00 108.00   0.50    0.12    --  104.25-108.00-178.94  116
 14  \w     82.00 108.00   0.50    0.12    --  104.25-120.00-120.00   52
 15  \w     37.00  93.00   0.50    0.12    --  104.25 -94.00-120.00  112
 16  \w     47.00 104.00   0.50    0.12    --  104.25 -94.00   0.00  114
 17  \w     48.00  73.00   0.50    0.12    --  104.25 -61.00 -60.00   50
 18  \w     36.00  67.00   0.50    0.12    --  104.25 -61.00   0.00   62
 19  \w     32.00  73.00   0.50    0.12    --  104.25 -61.00  30.00   82
 20  \w     44.00  73.00   0.50    0.12    --  104.25 -61.00 120.00   58
 21  \w     33.00  72.00   0.50    0.12    --  104.25 -61.00 -90.00   78
 22  \w     86.00 112.00   0.50    0.12    --  104.25 153.00 121.00   52
 23  \w    105.00 130.00   0.50    0.12    --  104.25 120.00 -36.00   50
 24  \w     15.00  40.00   0.50    0.07    --   42.00  86.00  -3.93   50
 25  \w     -3.00  22.00   0.50    0.07    --   30.00  98.00 -34.59   50
 26  \w    -44.00 -17.00   0.50    0.07    --    6.00 131.00 -72.72   54
 27  \w     15.00  40.00   0.50    0.07    --   42.00  89.00 -70.15   50
 28  \w     14.00  39.00   0.50    0.07    --   42.00  89.00  44.00   50
 29  \w    -14.00  11.00   0.50    0.07    --   18.00 101.00  92.74   50
 30  \w     -1.00  25.00   0.50    0.07    --   30.00  94.00 128.26   52
 31  \w     89.00 114.00   0.50    0.07    --   46.32 153.00 121.00   50
 32  \w     67.00  95.00   0.50    0.12    --   82.00  63.00  11.99   56
 33  \w     43.00  68.00   0.50    0.07    --   66.00  77.00  20.93   50
 34  \w     43.00  69.00   0.50    0.07    --   66.00  77.00 -54.11   52
 35  \w     31.00  57.00   0.50    0.07    --   54.00  77.00-125.70   52
 36  \w     35.00  79.00   0.50    0.07    --   58.00  77.00-152.78   88
 37  \w     82.00 109.00   0.50    0.07    --   58.00  77.00-152.78   54
 38  \w    138.00 169.00   0.50    0.12    --  104.25  77.00 -90.00   62
 39  \w     83.00 109.00   0.50    0.12    --  104.25  77.00 -90.00   52
 40  \w     36.00  67.00   0.50    0.07    --   58.00  76.00-175.55   62
 41  \w     40.00  70.00   0.50    0.07    --   62.00  76.00 -24.63   60
 42  \w     40.00  66.00   0.50    0.07    --   62.00  75.00  -1.89   52
 43  \w     34.00  94.00   0.50    0.07    --   54.00  76.00 167.20  120
 44  \w     52.00  95.00   0.50    0.07    --   74.00  75.00 177.89   86
 45  \w     37.00  65.00   0.50    0.07    --   58.00  74.00 141.72   56
 46  \w     33.00  66.00   0.50    0.07    --   54.00  74.00 117.31   66
 47  \w   -108.00 -74.00   0.50    0.07    --  -46.32 153.00 121.00   68
 48  \w    -63.00 -38.00   0.50    0.07    --  -46.32 153.00 121.00   50
 49  \w    -90.00 -10.00   0.50    0.07    --  -46.32 120.00 -36.00  160
 50  \w    -65.00 -40.00   0.50    0.12    -- -102.00  61.00 -60.00   50
 51  \w   -108.00 -66.00   0.50    0.12    -- -102.00 120.00 -36.00   84
 52  \w   -112.00 -30.00   0.50    0.12    -- -102.00 125.00 -90.00  164
 53  \w   -128.00-102.00   0.50    0.12    -- -102.00 153.00 121.00   52
 54  \w    -72.00 -35.00   0.50    0.07    --  -46.32 -37.00 -90.00   74
 55  \w   -113.00 -77.00   0.50    0.07    --  -46.32 -37.00 -90.00   72
 56  \w   -108.00 -82.00   0.50    0.07    --  -46.32 -37.00-150.00   52
 57  \w    -77.00 -36.00   0.50    0.07    --  -46.32 -37.00-150.00   82
 58  \w   -119.00 -78.00   0.50    0.07    --  -46.32 -37.00   0.00   82
 59  \w    -69.00 -34.00   0.50    0.07    --  -46.32 -37.00   0.00   70
 60  \w    -92.00 -67.00   0.50    0.12    --  -82.00 -58.00  15.98   50
 61  \w   -154.00 -76.00   0.50    0.12    --  -98.00 -76.00  35.81  156
 62  \w   -170.00 -76.00   0.50    0.12    --  -98.00 -76.00 109.45  188
 63  \w    -90.00 -65.00   0.50    0.12    --  -86.00 -74.00 133.40   50
 64  \w   -170.00 -75.00   0.50    0.12    --  -98.00 -77.00 127.48  190
 65  \w   -154.00-128.00   0.50    0.12    --  -86.00 -74.00 133.40   52
 66  \w    -83.00 -57.00   0.50    0.12    --  -78.00 -74.00 -20.09   52
 67  \w    -80.00 -55.00   0.50    0.12    --  -78.00 -76.00 -86.96   50
 68  \w   -101.00 -64.00   0.50    0.12    --  -86.00 -75.00-114.14   74
 69  \w   -129.00 -75.00   0.50    0.12    --  -98.00 -77.00-179.49  108
 70  \w   -172.00 -80.00   0.50    0.12    -- -102.00 -74.00-130.17  184
 71  \w   -160.00 -69.00   0.50    0.12    --  -90.00 -73.00-102.26  182
 72  \w    -86.00 -61.00   0.50    0.12    --  -82.00 -73.00  14.14   50
 73  \w    -99.00 -65.00   0.50    0.12    --  -86.00 -72.00   7.60   68
 74  \w   -115.00 -70.00   0.50    0.12    --  -90.00 -73.00 111.40   90
 75  \w    -95.00 -70.00   0.50    0.12    --  -90.00 -71.00  78.23   50
 76  \w    -90.00 -65.00   0.50    0.12    --  -86.00 -73.00 115.41   50
 77  \w    -81.00 -55.00   0.50    0.07    --  -74.00 -72.00 136.11   52
 78  \w    -94.00 -62.00   0.50    0.12    --  -82.00 -73.00 163.22   64
 79  \w    -81.00 -55.00   0.50    0.07    --  -74.00 -71.00 167.98   52
 80  \w   -129.00 -82.00   0.50    0.12    -- -102.00 -70.00 162.20   94
 81  \w   -160.00 -82.00   0.50    0.12    -- -102.00 -69.00 152.65  156
 82  \w    -81.00 -55.00   0.50    0.07    --  -74.00 -68.00  96.40   52
 83  \w   -174.00 -84.00   0.50    0.12    -- -102.00 -68.00  44.94  180
 84  \w   -170.00 -85.00   0.50    0.12    -- -102.00 -68.00  -4.30  170
 85  \w   -169.00 -84.00   0.50    0.12    -- -102.00 -68.00   1.49  170
 86  \w    -86.00 -60.00   0.50    0.12    --  -78.00 -69.00 -49.80   52
 87  \w    -75.00 -48.00   0.50    0.07    --  -66.00 -67.00  48.36   54
 88  \w    -76.00 -50.00   0.50    0.07    --  -70.00 -69.00 -75.38   52
 89  \w    -81.00 -55.00   0.50    0.07    --  -74.00 -68.00 -84.47   52
 90  \w    -91.00 -66.00   0.50    0.12    --  -86.00 -71.00-165.17   50
 91  \w    -90.00 -64.00   0.50    0.12    --  -82.00 -67.00-104.91   52
 92  \w    -80.00 -55.00   0.50    0.07    --  -74.00 -67.00 -53.82   50
 93  \w   -161.00 -73.00   0.50    0.12    --  -90.00 -67.00-173.93  176
 94  \w   -153.00-119.00   0.50    0.12    --  -90.00 -67.00 -95.12   68
 95  \w   -113.00 -74.00   0.50    0.12    --  -90.00 -67.00 -95.12   78
 96  \w   -165.00-126.00   0.50    0.12    --  -94.00 -67.00  85.67   78
 97  \w   -109.00 -75.00   0.50    0.12    --  -94.00 -67.00  85.67   68
 98  \w    -92.00 -64.00   0.50    0.12    --  -82.00 -66.00  75.30   56
 99  \w    -81.00 -55.00   0.50    0.07    --  -74.00 -67.00  78.12   52
100  \w    -84.00 -58.00   0.50    0.07    --  -74.00 -66.00  71.82   52
101  \w    -84.00 -58.00   0.50    0.07    --  -74.00 -65.00  59.97   52
102  \w    -97.00 -64.00   0.50    0.12    --  -82.00 -65.00  65.15   66
103  \w    -84.00 -58.00   0.50    0.07    --  -74.00 -65.00 172.57   52
104  \w   -109.00 -76.00   0.50    0.12    --  -94.00 -65.00  61.10   66
105  \w   -171.00 -84.00   0.50    0.12    -- -102.00 -65.00 -60.42  174
106  \w    -97.00 -72.00   0.50    0.12    --  -90.00 -66.00 -86.18   50
107  \w   -100.00 -64.00   0.50    0.12    --  -82.00 -64.00 -63.05   72
108  \w    -69.00 -44.00   0.50    0.07    --  -62.00 -66.00-157.75   50
109  \w    -74.00 -48.00   0.50    0.07    --  -66.00 -64.00-142.25   52
110  \w    -81.00 -56.00   0.50    0.07    --  -74.00 -65.00-170.16   50
111  \w    -99.00 -64.00   0.50    0.12    --  -82.00 -64.00-172.52   70
112  \w   -125.00 -78.00   0.50    0.12    --  -94.00 -65.00-151.92   94
113  \w   -166.00-140.00   0.50    0.12    --  -98.00 -64.00 -39.87   52
114  \w   -167.00 -78.00   0.50    0.12    --  -94.00 -64.00 -49.81  178
115  \w   -109.00 -80.00   0.50    0.12    --  -98.00 -64.00 -39.87   58
116  \w   -103.00 -78.00   0.50    0.12    --  -94.00 -64.00 -59.46   50
117  \w   -105.00 -79.00   0.50    0.12    --  -94.00 -63.00 -36.17   52
118  \w    -77.00 -52.00   0.50    0.07    --  -70.00 -64.00  33.71   50
119  \w    -75.00 -49.00   0.50    0.07    --  -66.00 -63.00  14.08   52
120  \w   -129.00 -79.00   0.50    0.12    --  -94.00 -63.00  49.26  100
121  \w    -95.00 -69.00   0.50    0.12    --  -86.00 -63.00 -38.86   52
122  \w    -96.00 -71.00   0.50    0.12    --  -86.00 -63.00 -75.71   50
123  \w    -84.00 -59.00   0.50    0.07    --  -74.00 -63.00-160.69   50
124  \w    -84.00 -58.00   0.50    0.07    --  -74.00 -62.00-158.51   52
125  \w   -115.00 -73.00   0.50    0.12    --  -90.00 -61.00-148.98   84
126  \w   -104.00 -79.00   0.50    0.12    --  -94.00 -63.00-134.99   50
127  \w   -100.00 -74.00   0.50    0.12    --  -90.00 -61.00  42.37   52
128  \w   -102.00 -77.00   0.50    0.12    --  -94.00 -61.00  38.56   50
129  \w   -112.00 -86.00   0.50    0.07    --  -46.32-153.00  80.00   52
130  \w   -130.00-104.00   0.50    0.12    -- -102.00-153.00  80.00   52
131  \w   -128.00 -94.00   0.50    0.12    -- -102.00-120.00-120.00   68
;
_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      -0.0928422000
_diffrn_orient_matrix_UB_12      -0.1458843000
_diffrn_orient_matrix_UB_13      -0.0236077000
_diffrn_orient_matrix_UB_21      0.0216851000
_diffrn_orient_matrix_UB_22      -0.0076341000
_diffrn_orient_matrix_UB_23      0.1144780000
_diffrn_orient_matrix_UB_31      -0.1633503000
_diffrn_orient_matrix_UB_32      0.0196758000
_diffrn_orient_matrix_UB_33      0.0128723000
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.385
_diffrn_reflns_theta_min         3.374
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54855
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0774P)^2^+0.1060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1406
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4026
_reflns_number_total             4883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06127e2.cif
_cod_data_source_block           jidongsheng_1014_auto
_cod_database_code               1566035
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.91
_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,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C25) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H00D(0.75) H00E(0.75) H00F(0.25) H00G(0.25) C25(0.75) H00Z(0.75)
 H(0.75) HA(0.75) C13(0.25) H1A(0.25) H1B(0.25) H1C(0.25)
4.a Ternary CH refined with riding coordinates:
 C1(H007)
4.b Secondary CH2 refined with riding coordinates:
 C2(H00D,H00E), C2(H00F,H00G)
4.c Aromatic/amide H refined with riding coordinates:
 C24(H00I), C26(H00J), C27(H00K), C7(H00L), C17(H00O), C9(H00P), C19(H00Q),
 C5(H00R), C23(H00V)
4.d Idealised Me refined as rotating group:
 C15(H00A,H00B,H00C), C21(H00H,H00M,H00N), C11(H00S,H00T,H00U), C3(H00W,H00X,
 H00Y), C25(H00Z,H,HA), C13(H1A,H1B,H1C)
;
_shelx_res_checksum              31260
_shelx_hkl_checksum              4258
_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 2.570
_oxdiff_exptl_absorpt_empirical_full_min 0.396