Synthesis of Mesoionic N-Heterocyclic Olefins and Catalytic Application for Hydroboration Reactions.
Zhang, Zengyu; Huang, Shiqing; Huang, Linwei; Xu, Xingyu; Zhao, Hongyan; Yan, Xiaoyu; The Journal of organic chemistry 85 (2020) 12036–12043; doi:10.1021/acs.joc.0c00257

data_4038827
_publ_section_title
;
 Synthesis of Mesoionic N-Heterocyclic Olefins and Catalytic Application
 for Hydroboration Reactions.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12036
_journal_page_last               12043
_journal_paper_doi               10.1021/acs.joc.0c00257
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C22 H27 N3'
_chemical_formula_sum            'C22 H27 N3'
_chemical_formula_weight         333.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.685(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.445(3)
_cell_length_b                   10.5768(13)
_cell_length_c                   8.1673(10)
_cell_measurement_reflns_used    4725
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.589
_cell_measurement_theta_min      3.635
_cell_volume                     1936.8(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      199.98
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12767
_diffrn_reflns_theta_full        29.64
_diffrn_reflns_theta_max         29.64
_diffrn_reflns_theta_min         3.63
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1210 before and 0.0489 after correction. The Ratio of minimum to maximum transmission is 0.9322. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0879P)^2^+1.0350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1778
_reflns_number_gt                1868
_reflns_number_total             2719
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00257_si_002.cif
_cod_data_source_block           mo_zzy20181130mes_0m_a
_cod_depositor_comments
'Adding full bibliography for 4038827--4038828.cif.'
_cod_database_code               4038827
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'