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_4038563
_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     direct
_audit_creation_date             2018-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                71.132(3)
_cell_angle_beta                 83.894(4)
_cell_angle_gamma                76.917(4)
_cell_formula_units_Z            6
_cell_length_a                   10.4950(6)
_cell_length_b                   14.6071(6)
_cell_length_c                   17.6793(6)
_cell_measurement_reflns_used    1336
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.2170
_cell_measurement_theta_min      2.7510
_cell_volume                     2496.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'XS (Sheldrick, 2008)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -47.00  53.00   1.00   22.50    --  -17.15  77.00-150.00  100
  2  \w    -87.00 -12.00   1.00   22.50    --  -17.15 -77.00  90.00   75
;
_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      -0.0259472000
_diffrn_orient_matrix_UB_12      0.0277283000
_diffrn_orient_matrix_UB_13      0.0265789000
_diffrn_orient_matrix_UB_21      -0.0221388000
_diffrn_orient_matrix_UB_22      0.0420548000
_diffrn_orient_matrix_UB_23      -0.0330795000
_diffrn_orient_matrix_UB_31      -0.0605517000
_diffrn_orient_matrix_UB_32      -0.0149188000
_diffrn_orient_matrix_UB_33      0.0024898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            51091
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.436
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     706
_refine_ls_number_reflns         10167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0792
_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^)+(0.1199P)^2^+1.1856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2122
_refine_ls_wR_factor_ref         0.2607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5473
_reflns_number_total             10167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01153_si_003.cif
_cod_data_source_block           wdh1083
_cod_database_code               4038563
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C19 H15 N5 O2'
_chemical_oxdiff_usercomment     YC057
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.955
_reflns_odcompleteness_completeness 73.26
_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:
 C29(H29), C30(H30), C33(H33), C38(H38), C39(H39), C40(H40), C41(H41),
 C42(H42), C44(H44), C45(H45), C47(H47), C48(H48), C3(H3), C4(H4), C7(H7),
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21),
  C22(H22), C55(H55), C56(H56), C59(H59), C64(H64), C65(H65), C66(H66),
 C67(H67), C68(H68), C70(H70), C71(H71), C73(H73), C74(H74)
2.b Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C26(H26A,H26B,H26C), C78(H78A,H78B,H78C)
;
_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 1.719
_oxdiff_exptl_absorpt_empirical_full_min 0.539