Sc(OTf)3-Catalyzed Chemodivergent Annulations of γ-Butyrolactone Fused Cyclopropanes with Anthranils.
Zhang, Xingyu; Feng, Manli; Yang, Gaosheng; Chai, Zhuo; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02444

data_4037658
_publ_section_title
;
 Sc(OTf)3-Catalyzed Chemodivergent Annulations of \g-Butyrolactone Fused
 Cyclopropanes with Anthranils.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02444
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H26 Cl N O5'
_chemical_formula_weight         552.00
_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
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 102.2960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3905(2)
_cell_length_b                   6.8267(2)
_cell_length_c                   18.0192(4)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      67.89
_cell_measurement_theta_min      2.51
_cell_volume                     1369.02(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-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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  0.0680
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36346
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.181
_diffrn_reflns_theta_min         2.510
_exptl_absorpt_coefficient_mu    1.595
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.1808
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1650 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.181(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0160P)^2^+0.3834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0760
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4213
_reflns_number_total             4950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02444_si_003.cif
_cod_data_source_block           cu_20180131a_0m_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037658
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.731
_shelx_estimated_absorpt_t_max   0.751
_shelx_res_checksum              30116
_shelx_hkl_checksum              88806