Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of <i>N</i>-Cyanomethylisoquinolinium Ylide.
Shi, Rong-Guo; Sun, Jing; Yan, Chao-Guo; ACS omega 2 (2017) 7820–7830; doi:10.1021/acsomega.7b01391

data_4516937
_publ_section_title
;
 Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms
 of <i>N</i>-Cyanomethylisoquinolinium Ylide.
;
_journal_issue                   11
_journal_name_full               'ACS omega'
_journal_page_first              7820
_journal_page_last               7830
_journal_paper_doi               10.1021/acsomega.7b01391
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         'C37 H26 N2 O4, C H2 Cl2 '
_chemical_formula_sum            'C38 H28 Cl2 N2 O4'
_chemical_formula_weight         647.52
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                71.77(2)
_cell_angle_beta                 84.647(14)
_cell_angle_gamma                62.20(5)
_cell_formula_units_Z            2
_cell_length_a                   11.995(6)
_cell_length_b                   12.221(8)
_cell_length_c                   12.496(8)
_cell_measurement_reflns_used    2650
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.60
_cell_measurement_theta_min      2.32
_cell_volume                     1536.0(18)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1224
_diffrn_reflns_av_unetI/netI     0.2220
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17066
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.024
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.2434
_refine_ls_R_factor_gt           0.0677
_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^)+(0.0402P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2028
_reflns_number_total             5805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b01391_si_002.cif
_cod_data_source_block           2i
_cod_original_cell_volume        1536.0(17)
_cod_database_code               4516937
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.941
_shelx_estimated_absorpt_t_max   0.945
_shelx_res_checksum              89871
_shelx_hkl_checksum              52765