Chemo-enzymatic synthesis of chiral 3-substituted tetrahydroquinolines by a sequential biocatalytic cascade and Buchwald–Hartwig cyclization
Xu, Zefei; Feng, Jinhui; Yao, Peiyuan; Wu, Qiaqing; Zhu, Dunming; Green Chemistry 25 (2023) 4667–4673; doi:10.1039/D3GC00047H

data_7246452
_publ_section_title
;
 Chemo-enzymatic synthesis of chiral 3-substituted tetrahydroquinolines by
 a sequential biocatalytic cascade and Buchwald--Hartwig cyclization
;
_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              4667
_journal_page_last               4673
_journal_paper_doi               10.1039/D3GC00047H
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H19 Cl N, Cl'
_chemical_formula_sum            'C13 H19 Cl2 N'
_chemical_formula_weight         260.19
_chemical_name_systematic
'(S)-N-(3-(2-chlorophenyl)-2-methylpropyl)prop-2-en-1-amine hydrochloride'
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dndcv
_audit_creation_date             2022-09-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-03 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.95940(10)
_cell_length_b                   10.73110(10)
_cell_length_c                   27.2017(3)
_cell_measurement_reflns_used    13015
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      78.6220
_cell_measurement_theta_min      4.4180
_cell_volume                     1447.67(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 pilatus
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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    -53.00  94.00   0.50    0.50    --    5.00  19.00 -14.00  294
  2  \w   -138.00   9.00   0.50    0.50    --  -49.00 -19.00 177.00  294
  3  \w   -199.00 -52.00   0.50    2.00    -- -110.00 -19.00 177.00  294
  4  \w   -168.00 -21.00   0.50    2.00    -- -110.00  19.00 -14.00  294
  5  \w    -79.00  40.00   0.50    0.50    --  -49.00  57.00-180.00  238
  6  \w    -82.00  40.00   0.50    0.50    --  -49.00  38.00 120.00  244
  7  \w   -144.00 -21.00   0.50    2.00    -- -110.00  72.00-180.00  246
  8  \w   -144.00 -21.00   0.50    2.00    -- -110.00  72.00 120.00  246
  9  \w   -199.00 -79.00   0.50    2.00    -- -110.00 -45.00-174.39  240
 10  \w   -144.00 -21.00   0.50    2.00    -- -110.00  72.00 -30.00  246
 11  \w   -144.00 -21.00   0.50    2.00    -- -110.00  72.00 150.00  246
 12  \w   -140.00 -21.00   0.50    2.00    -- -110.00  57.00-150.00  238
 13  \w   -143.00 -21.00   0.50    2.00    -- -110.00  38.00 -30.00  244
 14  \w    -84.00  35.00   0.50    0.50    --    5.00 -57.00 -60.00  238
 15  \w   -138.00 -17.00   0.50    0.50    --  -49.00 -64.00   5.84  242
 16  \w   -138.00 -17.00   0.50    0.50    --  -49.00 -66.00  85.70  242
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054471000
_diffrn_orient_matrix_UB_12      -0.0134760000
_diffrn_orient_matrix_UB_13      0.0563731000
_diffrn_orient_matrix_UB_21      -0.0772131000
_diffrn_orient_matrix_UB_22      0.1384957000
_diffrn_orient_matrix_UB_23      0.0049067000
_diffrn_orient_matrix_UB_31      -0.3008365000
_diffrn_orient_matrix_UB_32      -0.0353445000
_diffrn_orient_matrix_UB_33      -0.0022687000
_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  0.0323
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18528
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.255
_diffrn_reflns_theta_min         4.429
_diffrn_source                   Rotating-anode
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            'white solid'
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1170 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(5)
_refine_ls_extinction_coef       0.0015(5)
_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   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.1592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2963
_reflns_number_total             3066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc00047h2.cif
_cod_data_source_block           p20220902a
_cod_depositor_comments
'Adding full bibliography for 7246452--7246458.cif.'
_cod_database_code               7246452
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.580
_shelx_estimated_absorpt_t_min   0.473
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              42724
_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 1.576
_oxdiff_exptl_absorpt_empirical_full_min 0.701