Ring-Degenerate Rearrangement Resulting from the Azo Coupling Reaction of a 3-Aryl-1,3a,6a-triazapentalene.
Wang, Yingchun; Opsomer, Tomas; Van Meervelt, Luc; Dehaen, Wim; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01153

data_4038562
_publ_section_title
;
 Ring-Degenerate Rearrangement Resulting from the Azo Coupling Reaction of
 a 3-Aryl-1,3a,6a-triazapentalene.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01153
_journal_year                    2020
_chemical_formula_moiety         'C19 H15 N5 O2'
_chemical_formula_sum            'C19 H15 N5 O2'
_chemical_formula_weight         345.36
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-21
_audit_creation_method
;
Olex2 1.3
(compiled 2019.11.21 svn.r41b79517 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                60.722(10)
_cell_angle_beta                 78.914(6)
_cell_angle_gamma                71.326(8)
_cell_formula_units_Z            2
_cell_length_a                   9.1471(6)
_cell_length_b                   10.2389(12)
_cell_length_c                   10.4577(9)
_cell_measurement_reflns_used    2734
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1910
_cell_measurement_theta_min      2.7870
_cell_volume                     808.58(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -20.00  25.00   1.00   60.00    --  -17.07 -99.00 120.00   45
  2  \w    -43.00  55.00   1.00   60.00    --  -17.07  38.00 120.00   98
  3  \w    -20.00  25.00   1.00   60.00    --  -17.07 -99.00 -30.00   45
  4  \w    -93.00 -35.00   1.00   60.00    --  -17.07-178.00 -90.00   58
  5  \w     -7.00  91.00   1.00   60.00    --   18.87  38.00 -30.00   98
  6  \w    -50.00  40.00   1.00   60.00    --   18.87 -57.00-150.00   90
  7  \w    -54.00  44.00   1.00   60.00    --   18.87 -38.00 150.00   98
  8  \w    -20.00  61.00   1.00   60.00    --   18.87 -99.00   0.00   81
  9  \w    -25.00  92.00   1.00   60.00    --   18.87  19.00-150.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0238318000
_diffrn_orient_matrix_UB_12      -0.0695653000
_diffrn_orient_matrix_UB_13      -0.0066781000
_diffrn_orient_matrix_UB_21      -0.0308816000
_diffrn_orient_matrix_UB_22      0.0410979000
_diffrn_orient_matrix_UB_23      -0.0706750000
_diffrn_orient_matrix_UB_31      0.0720472000
_diffrn_orient_matrix_UB_32      0.0158880000
_diffrn_orient_matrix_UB_33      -0.0319085000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11341
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.393
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
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    1.418
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0690
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.2037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2010
_reflns_number_total             3299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01153_si_002.cif
_cod_data_source_block           wdh1101
_cod_database_code               4038562
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C19 H15 N5 O2'
_chemical_oxdiff_usercomment     YC317-2
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.953
_diffrn_oxdiff_ac4_digest_frames
;
014304954f4b643f3dfc1abc8cb60ba3ed00027a0b2
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_olex2_submission_original_sample_id YC137-2
_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 1.877
_oxdiff_exptl_absorpt_empirical_full_min 0.245