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_1563944
_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_moiety         'C17 H15 N O4'
_chemical_formula_sum            'C17 H15 N O4'
_chemical_formula_weight         297.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc27340j
_audit_creation_date             2020-09-20
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-01-24 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.3710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4401(3)
_cell_length_b                   6.6742(3)
_cell_length_c                   15.2681(6)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      66.72
_cell_measurement_theta_min      5.83
_cell_volume                     753.48(5)
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0451
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            51488
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.022
_diffrn_reflns_theta_max         67.022
_diffrn_reflns_theta_min         5.832
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0382P)^2^+0.0993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2620
_reflns_number_total             2643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02119b2.cif
_cod_data_source_block           cu_cj_12_94_0m_a
_cod_database_code               1563944
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.933
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              93193
_shelx_hkl_checksum              58760
_olex2_submission_special_instructions 'No special instructions were received'