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_4034171
_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         'C22 H41 N3'
_chemical_formula_sum            'C22 H41 N3'
_chemical_formula_weight         347.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.731(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6837(6)
_cell_length_b                   23.2094(17)
_cell_length_c                   9.7883(7)
_cell_measurement_reflns_used    5385
_cell_measurement_temperature    120.02(10)
_cell_measurement_theta_max      28.7010
_cell_measurement_theta_min      3.2190
_cell_volume                     2192.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      120.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -43.00 -17.00   1.00   74.25    --    3.60 -77.00 147.00   26
  2  \w    -46.00 -21.00   1.00   74.25    --   -3.90 -77.00 147.00   25
  3  \w    -26.00  91.00   1.00   74.25    --    3.60  57.00-150.00  117
  4  \w    -72.00 -46.00   1.00   74.25    --   -3.90 -77.00-120.00   26
  5  \w    -36.00  28.00   1.00   74.25    --   -3.90 -77.00-120.00   64
  6  \w    -77.00 -52.00   1.00   74.25    --   -3.90 -38.00-180.00   25
  7  \w    -39.00 -13.00   1.00   74.25    --   -3.90 -38.00-180.00   26
  8  \w    -62.00   9.00   1.00   74.25    --   -3.90 -82.00  30.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0510900000
_diffrn_orient_matrix_UB_12      -0.0219509000
_diffrn_orient_matrix_UB_13      -0.0017773000
_diffrn_orient_matrix_UB_21      0.0294187000
_diffrn_orient_matrix_UB_22      -0.0130023000
_diffrn_orient_matrix_UB_23      -0.0564302000
_diffrn_orient_matrix_UB_31      0.0438540000
_diffrn_orient_matrix_UB_32      -0.0168473000
_diffrn_orient_matrix_UB_33      0.0458018000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24373
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_min         2.728
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.053
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.261
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0527P)^2^+0.4647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3303
_reflns_number_total             4530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00774_si_002.cif
_cod_data_source_block           aj0112
_cod_database_code               4034171
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C19 N3 H22'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C20(H20), C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C9(H9A,H9B,
 H9C), C21(H21A,H21B,H21C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C), C12(H12A,
 H12B,H12C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C18(H18A,H18B,H18C),
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              10396
_shelx_hkl_checksum              45252
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.303
_oxdiff_exptl_absorpt_empirical_full_min 0.492