Synthesis of Quinone Methide Substituted Neonicotinoid Derivatives via 1,6-Conjugate Addition of N-Benzyl Nitro Ketene Aminals with para-Quinone Methides Accompanying Oxidation
Wang, Bao-Qu; Luo, Qin; Xiao, Qiang; Lin, Jun; Yan, Sheng-Jiao; ACS Sustainable Chemistry & Engineering 5 (2017) 8382–; doi:10.1021/acssuschemeng.7b02166

data_4517024
_publ_section_title
;
 Synthesis of Quinone Methide Substituted Neonicotinoid Derivatives via
 1,6-Conjugate Addition of N-Benzyl Nitro Ketene Aminals with para-Quinone
 Methides Accompanying Oxidation
;
_journal_issue                   9
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              8382
_journal_paper_doi               10.1021/acssuschemeng.7b02166
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C32 H34 F3 N3 O3'
_chemical_formula_weight         565.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 116.320(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.960(3)
_cell_length_b                   19.710(4)
_cell_length_c                   15.380(3)
_cell_measurement_reflns_used    11141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2009
_cell_measurement_theta_min      4584
_cell_volume                     3793.1(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21551
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.149
_diffrn_reflns_theta_min         1.803
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.990
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         6770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1856
_refine_ls_R_factor_gt           0.1233
_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^)+(0.3000P)^2^+0.2600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4162
_refine_ls_wR_factor_ref         0.4529
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3027
_reflns_number_total             6770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc7b02166_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C21 H22 F2 N2 O2'
_cod_original_formula_units_Z    6
_cod_original_formula_weight     372.4
_cod_database_code               4517024
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2014-3
_shelx_res_checksum              68874
_shelx_hkl_checksum              19272
_platon_squeeze_void_probe_radius 1.20