Synthesis of spiro[indane-1,3-dione-1-pyrrolines] via copper-catalyzed heteroannulation of ketoxime acetates with 2-arylideneindane-1,3-diones
Duan, Jindian; Cheng, Yuyu; Li, Rou; Li, Pengfei; Organic Chemistry Frontiers 3 (2016) 1614–; doi:10.1039/C6QO00454G

data_1553529
_publ_section_title
;
 Synthesis of spiro[indane-1,3-dione-1-pyrrolines] via copper-catalyzed
 heteroannulation of ketoxime acetates with 2-arylideneindane-1,3-diones
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1614
_journal_paper_doi               10.1039/C6QO00454G
_journal_volume                  3
_journal_year                    2016
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-12-29 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                101.875(7)
_cell_angle_beta                 106.962(8)
_cell_angle_gamma                96.397(7)
_cell_formula_units_Z            2
_cell_length_a                   9.30340(10)
_cell_length_b                   9.6541(2)
_cell_length_c                   11.6687(8)
_cell_measurement_reflns_used    11207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      7.00
_cell_volume                     964.39(9)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13309
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.334
_diffrn_reflns_theta_min         7.023
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0753P)^2^+0.1682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3039
_reflns_number_total             3411
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00454g2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        964.39(8)
_cod_database_code               1553529
_shelxl_version_number           2014-3
_shelx_res_checksum              30430
_shelx_hkl_checksum              22306