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_4034170
_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         'C19 H35 N3'
_chemical_formula_sum            'C19 H35 N3'
_chemical_formula_weight         305.50
_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             2017-12-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.75(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.158(4)
_cell_length_b                   7.8326(18)
_cell_length_c                   17.317(6)
_cell_measurement_reflns_used    1555
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      25.6930
_cell_measurement_theta_min      2.9600
_cell_volume                     1881.9(10)
_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      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_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      9.00  34.00   1.00  123.14    --    3.50  51.00 168.00   25
  2  \w     26.00  51.00   1.00  123.14    --   -3.80  51.00 168.00   25
  3  \w    -69.00 -27.00   1.00  123.14    --   -3.80 -51.00  22.00   42
  4  \w    -63.00  12.00   1.00  123.14    --   -3.80 -82.00 150.00   75
  5  \w    -62.00 -11.00   1.00  123.14    --   -3.80 -82.00-150.00   51
  6  \w     -6.00  34.00   1.00  123.14    --   -3.80 -82.00-150.00   40
  7  \w    -61.00 -35.00   1.00  123.14    --   -3.80 -77.00 120.00   26
  8  \w     -9.00  33.00   1.00  123.14    --   -3.80 -77.00 120.00   42
  9  \w    -57.00 -31.00   1.00  123.14    --   -3.80 -82.00-180.00   26
 10  \w    -63.00  24.00   1.00  123.14    --   -3.80 -82.00   0.00   87
;
_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      0.0471848000
_diffrn_orient_matrix_UB_12      0.0061439000
_diffrn_orient_matrix_UB_13      0.0011473000
_diffrn_orient_matrix_UB_21      -0.0133019000
_diffrn_orient_matrix_UB_22      -0.0557814000
_diffrn_orient_matrix_UB_23      -0.0351672000
_diffrn_orient_matrix_UB_31      -0.0144904000
_diffrn_orient_matrix_UB_32      0.0710710000
_diffrn_orient_matrix_UB_33      -0.0276763000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2304
_diffrn_reflns_av_unetI/netI     0.1771
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17916
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         2.901
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.0900
_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^)+(0.0795P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.2073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2131
_reflns_number_total             3455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00774_si_002.cif
_cod_data_source_block           aj0118
_cod_original_cell_volume        1881.8(10)
_cod_database_code               4034170
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C17 H22 N3'
_reflns_odcompleteness_completeness 97.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Idealised Me refined as rotating group:
 C008(H00A,H00B,H00C), C00D(H00D,H00E,H00F), C00E(H00G,H00H,H00I), C00F(H00J,
 H00K,H00L), C00G(H00M,H00N,H00O), C00H(H00P,H00Q,H00R), C00I(H00S,H00T,H00U),
 C00J(H00V,H00W,H00X), C00K(H00Y,H,HA), C00L(H00Z,HB,HC), C00M(H00,HD,HE)
;
_shelx_res_checksum              41158
_shelx_hkl_checksum              52120
_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 6.730
_oxdiff_exptl_absorpt_empirical_full_min 0.150