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_4518182
_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            'C8 H15 Cl O'
_chemical_formula_weight         162.65
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-12-16T11:39:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.567(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2973(2)
_cell_length_b                   5.2861(2)
_cell_length_c                   12.6948(5)
_cell_measurement_reflns_used    2412
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.154
_cell_measurement_theta_min      3.197
_cell_volume                     421.77(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123(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 0.962
_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      -0.0399824
_diffrn_orient_matrix_UB_12      -0.0612784
_diffrn_orient_matrix_UB_13      -0.0468276
_diffrn_orient_matrix_UB_21      -0.0769585
_diffrn_orient_matrix_UB_22      -0.0632398
_diffrn_orient_matrix_UB_23      0.0288722
_diffrn_orient_matrix_UB_31      -0.0722405
_diffrn_orient_matrix_UB_32      0.1012586
_diffrn_orient_matrix_UB_33      -0.0103028
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7255
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.035
_diffrn_reflns_theta_min         1.607
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.81184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.29a (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prism
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.035
_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^)+(0.0257P)^2^+0.0511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0716
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                1716
_reflns_number_total             1900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04097_si_002.cif
_cod_data_source_block           3c
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4518182
_shelx_res_checksum              89780
_shelx_hkl_checksum              39561