Synthesis of a sacubitril precursor via the construction of one-pot chemoenzymatic cascades
Chen, Long; Qu, Ge; Cai, Zhiqiang; Yuan, Bo; Sun, Zhoutong; Catalysis Science & Technology 14 (2024) 2817–2824; doi:10.1039/D4CY00145A

data_1571407
_publ_section_title
;
 Synthesis of a sacubitril precursor via the construction of one-pot
 chemoenzymatic cascades
;
_journal_issue                   10
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              2817
_journal_page_last               2824
_journal_paper_doi               10.1039/D4CY00145A
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34
_chemical_name_systematic
(3R,5S)-5-([1,1'-biphenyl]-4-ylmethyl)-3-methylpyrrolidin-2-one
_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     iterative
_audit_creation_date             2024-01-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-31 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.902(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6039(3)
_cell_length_b                   8.8338(2)
_cell_length_c                   15.3191(3)
_cell_measurement_reflns_used    14366
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1090
_cell_measurement_theta_min      2.8770
_cell_volume                     1433.14(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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     72.00 118.00   0.50    0.50    --   65.76  30.00   0.00   92
  2  \w     72.00 118.00   0.50    0.50    --   65.76  30.00 -30.00   92
  3  \w     92.00 138.00   0.50    0.50    --   85.77  30.00  30.00   92
  4  \w     61.00 107.00   0.50    0.50    --   54.62  30.00 -60.00   92
  5  \w     61.00 107.00   0.50    0.50    --   54.62  30.00-120.00   92
  6  \w     92.00 138.00   0.50    0.50    --   85.77  30.00-180.00   92
  7  \w     92.00 138.00   0.50    0.50    --   85.77  30.00-120.00   92
  8  \w     92.00 138.00   0.50    0.50    --   85.77  30.00  90.00   92
  9  \w     85.00 131.00   0.50    0.50    --   78.60  30.00 120.00   92
 10  \w     61.00 107.00   0.50    0.50    --   54.62  30.00  60.00   92
 11  \w    -97.00 -28.00   0.50    0.50    --  -77.41 111.00 -60.00  138
 12  \w    -96.00 -33.00   0.50    0.50    --  -82.00 111.00 -90.00  126
 13  \w    -97.00 -28.00   0.50    0.50    --  -77.41 111.00 -30.00  138
 14  \w    -97.00 -28.00   0.50    0.50    --  -77.41 111.00-120.00  138
 15  \w    -97.00 -28.00   0.50    0.50    --  -77.41 111.00   0.00  138
 16  \w    -97.00 -28.00   0.50    0.50    --  -77.41 111.00-180.00  138
 17  \w    -97.00 -28.00   0.50    0.50    --  -77.41 111.00  30.00  138
 18  \w    -97.00 -28.00   0.50    0.50    --  -77.41 111.00  60.00  138
 19  \w    -96.00 -33.00   0.50    0.50    --  -82.00 111.00 120.00  126
 20  \w    -97.00 -28.00   0.50    0.50    --  -77.41 111.00 150.00  138
 21  \w   -129.00 -41.00   0.50    0.50    --  -77.41 -15.00 120.00  176
 22  \w   -110.00 -65.00   0.50    0.50    --  -57.84 -30.00 120.00   90
 23  \w   -110.00 -65.00   0.50    0.50    --  -57.84 -30.00 150.00   90
 24  \w   -134.00 -89.00   0.50    0.50    --  -82.00 -30.00  90.00   90
 25  \w   -134.00 -89.00   0.50    0.50    --  -82.00 -30.00  30.00   90
 26  \w   -134.00 -89.00   0.50    0.50    --  -82.00 -30.00 120.00   90
 27  \w   -134.00 -89.00   0.50    0.50    --  -82.00 -30.00   0.00   90
 28  \w   -110.00 -65.00   0.50    0.50    --  -57.84 -30.00  30.00   90
 29  \w   -130.00 -85.00   0.50    0.50    --  -77.41 -30.00 -90.00   90
 30  \w   -134.00 -89.00   0.50    0.50    --  -82.00 -30.00-120.00   90
 31  \w   -134.00 -89.00   0.50    0.50    --  -82.00 -30.00-150.00   90
 32  \w   -110.00 -65.00   0.50    0.50    --  -57.84 -30.00-150.00   90
 33  \w   -134.00 -46.00   0.50    0.50    --  -82.00 -15.00 -90.00  176
 34  \w   -129.00 -41.00   0.50    0.50    --  -77.41 -15.00 -60.00  176
 35  \w   -129.00 -41.00   0.50    0.50    --  -77.41 -15.00  30.00  176
 36  \w     42.00  93.00   0.50    0.50    --   85.77 -95.00  90.00  102
 37  \w     11.00  84.00   0.50    0.50    --   54.62-125.00 150.00  146
 38  \w     30.00  96.00   0.50    0.50    --   78.60-111.00 150.00  132
 39  \w     30.00  96.00   0.50    0.50    --   78.60-111.00 -90.00  132
 40  \w     42.00  93.00   0.50    0.50    --   85.77 -95.00 -90.00  102
 41  \w     42.00  93.00   0.50    0.50    --   85.77 -95.00-150.00  102
 42  \w     11.00  63.00   0.50    0.50    --   54.62 -95.00-120.00  104
 43  \w     35.00  87.00   0.50    0.50    --   78.60 -95.00 120.00  104
 44  \w     22.00  74.00   0.50    0.50    --   65.76 -95.00  30.00  104
 45  \w     11.00  63.00   0.50    0.50    --   54.62 -95.00 -30.00  104
 46  \w     11.00  63.00   0.50    0.50    --   54.62 -95.00-180.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1259240000
_diffrn_orient_matrix_UB_12      0.0055595000
_diffrn_orient_matrix_UB_13      -0.0547510000
_diffrn_orient_matrix_UB_21      -0.0507793000
_diffrn_orient_matrix_UB_22      -0.1317232000
_diffrn_orient_matrix_UB_23      0.0539514000
_diffrn_orient_matrix_UB_31      -0.0522633000
_diffrn_orient_matrix_UB_32      0.1141519000
_diffrn_orient_matrix_UB_33      0.0650336000
_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  0.0798
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27270
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.188
_diffrn_reflns_theta_min         2.888
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (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    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1907 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(14)
_refine_ls_extinction_coef       0.0034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5318
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0645P)^2^+0.0033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                4874
_reflns_number_total             5318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cy00145a2.cif
_cod_data_source_block           zbw-3-1_auto
_cod_depositor_comments          'Adding full bibliography for 1571407.cif.'
_cod_database_code               1571407
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C18H19NO
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 99.96
_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.a Ternary CH refined with riding coordinates:
 C005(H005), C00A(H00A), C00O(H00O), C00V(H00V)
2.b Secondary CH2 refined with riding coordinates:
 C00S(H00C,H00D), C00W(H00G,H00S), C00Z(H00E,H00F), C013(H01G,H01H)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), C009(H009), C00B(H00B), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U), C00X(H00X), C00Y(H00Y),
 C011(H011), C012(H012)
2.d Idealised Me refined as rotating group:
 C010(H01D,H01E,H01F), C014(H01A,H01B,H01C)
;
_shelx_res_checksum              38673
_shelx_hkl_checksum              47108
_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 3.913
_oxdiff_exptl_absorpt_empirical_full_min 0.137