Multienzymatic Stereoselective Reduction of Tetrasubstituted Cyclic Enones to Halohydrins with Three Contiguous Stereogenic Centers
Venturi, Silvia; Brenna, Elisabetta; Colombo, Danilo; Fraaije, Marco W.; Gatti, Francesco G.; Macchi, Piero; Monti, Daniela; Trajkovic, Milos; Zamboni, Emilio; ACS Catalysis  (2020) 13050–13057; doi:10.1021/acscatal.0c04097

data_4518181
_publ_section_title
;
 Multienzymatic Stereoselective Reduction of Tetrasubstituted Cyclic
 Enones to Halohydrins with Three Contiguous Stereogenic Centers
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              13050
_journal_page_last               13057
_journal_paper_doi               10.1021/acscatal.0c04097
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C7 H13 Cl O'
_chemical_formula_weight         148.62
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-12-03T16:44:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.24000(10)
_cell_length_b                   6.28050(10)
_cell_length_c                   23.9605(6)
_cell_measurement_reflns_used    2997
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.498
_cell_measurement_theta_min      3.337
_cell_volume                     788.54(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0349132
_diffrn_orient_matrix_UB_12      0.0086563
_diffrn_orient_matrix_UB_13      -0.0285125
_diffrn_orient_matrix_UB_21      -0.0089426
_diffrn_orient_matrix_UB_22      0.112475
_diffrn_orient_matrix_UB_23      0.0018163
_diffrn_orient_matrix_UB_31      0.1304815
_diffrn_orient_matrix_UB_32      0.0053736
_diffrn_orient_matrix_UB_33      0.0077471
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6721
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.146
_diffrn_reflns_theta_min         1.7
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 507 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.1812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                1538
_reflns_number_total             1767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04097_si_002.cif
_cod_data_source_block           3b
_cod_database_code               4518181
_shelx_res_checksum              11173
_shelx_hkl_checksum              38882