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_4038828
_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         'C28 H39 N3'
_chemical_formula_sum            'C28 H39 N3'
_chemical_formula_weight         417.62
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                66.588(3)
_cell_angle_beta                 81.982(3)
_cell_angle_gamma                72.540(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9279(10)
_cell_length_b                   12.3384(13)
_cell_length_c                   13.3669(14)
_cell_measurement_reflns_used    5209
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      27.251
_cell_measurement_theta_min      2.609
_cell_volume                     1288.6(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15766
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         2.609
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0839 before and 0.0486 after correction. The Ratio of minimum to maximum transmission is 0.9292. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0666
_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^)+(0.0679P)^2^+0.5994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1768
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3752
_reflns_number_total             5895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00257_si_003.cif
_cod_data_source_block           mo_zzy20181126dipmes_0m_a
_cod_depositor_comments
'Adding full bibliography for 4038827--4038828.cif.'
_cod_database_code               4038828
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C26(H26), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C19(H19), C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C28(H28A,H28B,H28C), C25(H25A,H25B,H25C), C24(H24A,H24B,
 H24C), C13(H13A,H13B,H13C), C27(H27A,H27B,H27C), C12(H12A,H12B,H12C), C16(H16A,
 H16B,H16C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              26344
_shelx_hkl_checksum              62062
_olex2_submission_special_instructions 'No special instructions were received'