Influence of <i>N</i>-Substitution on the Formation and Oxidation of NHC-CAAC-Derived Triazaalkenes.
Mandal, Debdeep; Dolai, Ramapada; Kumar, Ravi; Suhr, Simon; Chrysochos, Nicolas; Kalita, Pankaj; Narayanan, Ramakirushnan Suriya; Rajaraman, Gopalan; Schulzke, Carola; Sarkar, Biprajit; Chandrasekhar, Vadapalli; Jana, Anukul; The Journal of organic chemistry 84 (2019) 8899–8909; doi:10.1021/acs.joc.9b00774

data_4034173
_publ_section_title
;
 Influence of <i>N</i>-Substitution on the Formation and Oxidation of
 NHC-CAAC-Derived Triazaalkenes.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8899
_journal_page_last               8909
_journal_paper_doi               10.1021/acs.joc.9b00774
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C F3 O3 S, C21 H40 N3'
_chemical_formula_sum            'C22 H40 F3 N3 O3 S'
_chemical_formula_weight         483.63
_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     direct
_audit_creation_date             2017-07-10
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                112.115(2)
_cell_angle_beta                 102.089(2)
_cell_angle_gamma                101.858(2)
_cell_formula_units_Z            4
_cell_length_a                   13.3215(17)
_cell_length_b                   14.6644(9)
_cell_length_c                   14.9986(9)
_cell_measurement_reflns_used    6975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.33
_cell_volume                     2520.1(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31215
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.504
_diffrn_reflns_theta_min         1.545
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_min  0
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.0603 before and 0.0346 after correction. The Ratio of minimum to maximum transmission is 0.8379. The \l/2 correction factor is 0.0015.'
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     609
_refine_ls_number_reflns         10050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0584P)^2^+1.3697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7423
_reflns_number_total             10050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00774_si_002.cif
_cod_data_source_block           aj_dm_v1
_cod_database_code               4034173
_shelx_shelxl_version_number     2016/4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00P(H00P), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C19A(H19A,H19B,H19C), C15A(H15A,H15B,H15C), C8A(H8AA,
 H8AB,H8AC), C18A(H18A,H18B,H18C), C16A(H16A,H16B,H16C), C11(H11D,H11E,H11F),
 C14A(H14A,H14B,H14C), C10(H10D,H10E,H10F), C11A(H11A,H11B,H11C), C14(H14D,H14E,
 H14F), C01E(H01A,H01B,H01C), C17(H17D,H17E,H17F), C9A(H9AA,H9AB,H9AC),
 C15(H15D,H15E,H15F), C13A(H13A,H13B,H13C), C18(H18D,H18E,H18F), C10A(H10A,H10B,
 H10C), C19(H19D,H19E,H19F), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C13(H13D,
 H13E,H13F), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'