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_4516938
_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         'C36 H23 Cl N2 O4, C2 H3 N'
_chemical_formula_sum            'C38 H26 Cl N3 O4'
_chemical_formula_weight         624.07
_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                103.752(4)
_cell_angle_beta                 94.826(4)
_cell_angle_gamma                118.541(4)
_cell_formula_units_Z            2
_cell_length_a                   11.8189(15)
_cell_length_b                   12.2358(15)
_cell_length_c                   12.6250(16)
_cell_measurement_reflns_used    7161
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.33
_cell_measurement_theta_min      2.18
_cell_volume                     1515.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0344
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_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            21145
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.978
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0942P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3933
_reflns_number_total             5902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b01391_si_002.cif
_cod_data_source_block           2l
_cod_database_code               4516938
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              17587
_shelx_hkl_checksum              37332