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_4518183
_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            'C9 H15 Cl O2'
_chemical_formula_weight         190.66
_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             2020-03-14T17:32:16-00:00
_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                   7.28870(10)
_cell_length_b                   9.0165(2)
_cell_length_c                   15.2516(3)
_cell_measurement_reflns_used    3643
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.973
_cell_measurement_theta_min      5.672
_cell_volume                     1002.31(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_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 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1297358
_diffrn_orient_matrix_UB_12      0.0383232
_diffrn_orient_matrix_UB_13      0.0764091
_diffrn_orient_matrix_UB_21      -0.1619614
_diffrn_orient_matrix_UB_22      0.0108968
_diffrn_orient_matrix_UB_23      -0.0645459
_diffrn_orient_matrix_UB_31      -0.0406323
_diffrn_orient_matrix_UB_32      -0.1660915
_diffrn_orient_matrix_UB_33      0.0134969
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9194
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.163
_diffrn_reflns_theta_min         5.7
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.06
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.83096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.951
_exptl_crystal_size_mid          0.572
_exptl_crystal_size_min          0.386
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.1043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                1828
_reflns_number_total             1904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c04097_si_002.cif
_cod_data_source_block           3g
_cod_database_code               4518183
_shelx_res_checksum              57319
_shelx_hkl_checksum              42140