Synthesis of Pyrrolotriazoloisoquinoline Frameworks by Intramolecular Cu-Mediated or Free Radical Arylation of Triazoles.
Funt, Liya D.; Tomashenko, Olesya A.; Mosiagin, Ivan P.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; The Journal of organic chemistry 82 (2017) 7583–7594; doi:10.1021/acs.joc.7b01341

data_4037515
_publ_section_title
;
 Synthesis of Pyrrolotriazoloisoquinoline Frameworks by Intramolecular
 Cu-Mediated or Free Radical Arylation of Triazoles.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7583
_journal_page_last               7594
_journal_paper_doi               10.1021/acs.joc.7b01341
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H18 N4'
_chemical_formula_sum            'C25 H18 N4'
_chemical_formula_weight         374.43
_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_Hall           'P -4 2n'
_space_group_name_H-M_alt        'P -4 21 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.76262(16)
_cell_length_b                   21.76262(16)
_cell_length_c                   7.96088(12)
_cell_measurement_reflns_used    9260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2300
_cell_measurement_theta_min      4.0350
_cell_volume                     3770.37(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -22.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000 -150.0000 55

  2 omega  -35.00   14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000    0.0000 49

  3 omega   47.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  -99.0000   90.0000 29

  4 omega   43.00  106.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -150.0000 63

  5 omega   40.00   98.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 58

  6 omega   69.00  106.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   30.0000 37

  7 omega   37.00  138.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000  120.0000 101

  8 omega  -30.00    0.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -19.0000 -150.0000 30

  9 omega  -90.00  -16.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000  -30.0000 74

 10 omega   11.00   37.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354   77.0000  -60.0000 26

 11 omega   80.00  105.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 25

 12 omega   87.00  167.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 80

 13 omega   79.00  105.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 26

 14 omega   83.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 26

 15 omega   83.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 26

 16 omega   83.00  110.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 27

 17 omega   79.00  105.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 26

 18 omega   79.00  105.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0455583000
_diffrn_orient_matrix_UB_12      -0.0539855000
_diffrn_orient_matrix_UB_13      0.0124731000
_diffrn_orient_matrix_UB_21      0.0540011000
_diffrn_orient_matrix_UB_22      0.0448314000
_diffrn_orient_matrix_UB_23      -0.0248435000
_diffrn_orient_matrix_UB_31      0.0040943000
_diffrn_orient_matrix_UB_32      0.0092261000
_diffrn_orient_matrix_UB_33      0.1915983000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17273
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.498
_diffrn_reflns_theta_min         2.872
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0430P)^2^+0.4833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3558
_reflns_number_total             3695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01341_si_002.cif
_cod_data_source_block           ole227
_cod_original_cell_volume        3770.36(8)
_cod_database_code               4037515
_chemical_oxdiff_formula         'C21 h16 n4'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(4) 0.1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'