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_4037659
_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_formula_moiety         'C30 H24 Cl N O2'
_chemical_formula_sum            'C30 H24 Cl N O2'
_chemical_formula_weight         465.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.828(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.318(3)
_cell_length_b                   8.418(2)
_cell_length_c                   26.443(8)
_cell_measurement_reflns_used    7150
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.54
_cell_volume                     2291.6(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18663
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        24.983
_diffrn_reflns_theta_max         24.983
_diffrn_reflns_theta_min         1.544
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5356
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     756
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0711
_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^)+(0.0354P)^2^+3.9473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2916
_reflns_number_total             3863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02444_si_004.cif
_cod_data_source_block           190428a_0m_a
_cod_original_cell_volume        2291.7(12)
_cod_database_code               4037659
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C13 \\sim C8 \\sim C19 \\sim C15 \\sim C9 \\sim C12 \\sim C14 \\sim C10 \\sim
C25 \\sim C7 \\sim C16 \\sim C11 \\sim C6 \\sim C24 \\sim C20 \\sim C1 \\sim
C17 \\sim C26 \\sim C21 \\sim C23 \\sim C18 \\sim C22 \\sim C5 \\sim C27 \\sim
C30 \\sim C2 \\sim C4 \\sim C28 \\sim C3 \\sim C29: within 3.8A with sigma of
0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C14(H14), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C11(H11), C24(H24), C20(H20), C1(H1A), C26(H26), C21(H21),
 C23(H23), C22(H22), C5(H5), C27(H27), C30(H30), C2(H2), C4(H4), C28(H28),
 C3(H3), C29(H29)
;
_shelx_res_checksum              54653
_shelx_hkl_checksum              44467
_olex2_submission_special_instructions 'No special instructions were received'