Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels-Alder reaction versus aryne-mediated domino process.
Kopchuk, Dmitry S.; Nikonov, Igor L.; Khasanov, Albert F.; Giri, Kousik; Santra, Sougata; Kovalev, Igor S.; Nosova, Emiliya V.; Gundala, Sravya; Venkatapuram, Padmavathi; Zyryanov, Grigory V.; Majee, Adinath; Chupakhin, Oleg N.; Organic & biomolecular chemistry 16 (2018) 5119–5135; doi:10.1039/c8ob00847g

data_7156227
_publ_section_title
;
 Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with
 arynes: inverse demand aza-Diels-Alder reaction versus aryne-mediated
 domino process.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5119
_journal_page_last               5135
_journal_paper_doi               10.1039/c8ob00847g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C21 H12 Br N3'
_chemical_formula_sum            'C21 H12 Br N3'
_chemical_formula_weight         386.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-03-26
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2017-07-14 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.138(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.8659(10)
_cell_length_b                   10.1158(4)
_cell_length_c                   8.8637(5)
_cell_measurement_reflns_used    3444
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.9740
_cell_measurement_theta_min      2.2050
_cell_volume                     1670.11(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.8950
_diffrn_measurement_details
;
  1 omega  -24.00   15.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000  120.0000 39

  2 omega  -20.00   13.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000  -90.0000 33

  3 omega   42.00   95.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -       23.1362  178.0000 -180.0000 53

  4 omega    3.00   90.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -       23.1362   57.0000   30.0000 87

  5 omega   -2.00   87.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -       23.1362   38.0000  -60.0000 89

  6 omega  -49.00   49.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -       23.1362  -38.0000  120.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0038798000
_diffrn_orient_matrix_UB_12      -0.0515084000
_diffrn_orient_matrix_UB_13      0.0524009000
_diffrn_orient_matrix_UB_21      -0.0216292000
_diffrn_orient_matrix_UB_22      -0.0358067000
_diffrn_orient_matrix_UB_23      -0.0589145000
_diffrn_orient_matrix_UB_31      0.0310955000
_diffrn_orient_matrix_UB_32      -0.0313678000
_diffrn_orient_matrix_UB_33      -0.0187017000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14628
_diffrn_reflns_theta_full        28.2205
_diffrn_reflns_theta_max         30.8290
_diffrn_reflns_theta_min         2.0132
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.180
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.0920P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1341
_reflns_number_gt                3352
_reflns_number_total             4697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob00847g2.cif
_cod_data_source_block           exp_110
_cod_depositor_comments
'Adding full bibliography for 7156227--7156229.cif.'
_cod_original_cell_volume        1670.12(15)
_cod_database_code               7156227
_chemical_oxdiff_formula         C10H10N3O
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22