Catalytic Enantioselective Synthesis of Benzocyclobutenols and Cyclobutanols via A Sequential Reduction/C-H Functionalization
Chen, Jun; Shi, Zhan; Li, Chunyu; Lu, Ping; Chemical Science  (2021) –; doi:10.1039/D1SC02119B

data_1563943
_publ_section_title
;
 Catalytic Enantioselective Synthesis of Benzocyclobutenols and
 Cyclobutanols via A Sequential Reduction/C-H Functionalization
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02119B
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2737g2
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-01-26 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5336(2)
_cell_length_b                   7.0040(2)
_cell_length_c                   25.2509(8)
_cell_measurement_reflns_used    8437
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      140.254
_cell_measurement_theta_min      10.51
_cell_volume                     1155.51(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8786
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.471
_diffrn_reflns_theta_min         7.014
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 812 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_coef       0.033(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0539P)^2^+0.1648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2004
_reflns_number_total             2031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02119b2.cif
_cod_data_source_block           cu_d8v20345_0m
_cod_database_code               1563943
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.924
_shelxl_version_number           2013-4
_shelx_res_checksum              58178
_shelx_hkl_checksum              77807