Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts
Li, Bao-Sheng; Wang, Yuhuang; Jin, Zhichao; Chi, Yonggui Robin; Chem. Sci. 6 (2015) 6008–; doi:10.1039/C5SC01972A

data_1529216
_publ_section_title
;
 Cycloaddition of cyclobutenone and azomethine imine enabled by chiral
 isothiourea organic catalysts
;
_journal_issue                   10
_journal_name_full               'Chem. Sci.'
_journal_page_first              6008
_journal_paper_doi               10.1039/C5SC01972A
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H21 Cl N2 O2'
_chemical_formula_weight         428.90
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2014-12-24 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5286(2)
_cell_length_b                   10.2653(3)
_cell_length_c                   21.7873(5)
_cell_measurement_reflns_used    4582
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      24.3014
_cell_measurement_theta_min      2.7264
_cell_volume                     2131.10(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5299
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.227
_refine_ls_abs_structure_details
;
Flack x determined using 1806 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.4085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                4551
_reflns_number_total             5299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc01972a2.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1529216.cif.'
_cod_database_code               1529216
_shelx_res_checksum              37846
_shelx_hkl_checksum              14496