3-Substituted Benzo[ e][1,2,4]triazines: Synthesis and Electronic Effects of the C(3) Substituent.
Bodzioch, Agnieszka; Pomikło, Dominika; Celeda, Małgorzata; Pietrzak, Anna; Kaszyński, Piotr; The Journal of organic chemistry 84 (2019) 6377–6394; doi:10.1021/acs.joc.9b00716

data_4033675
_publ_section_title
;
 3-Substituted Benzo[ e][1,2,4]triazines: Synthesis and Electronic Effects
 of the C(3) Substituent.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6377
_journal_page_last               6394
_journal_paper_doi               10.1021/acs.joc.9b00716
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C21 H14 N4 O2'
_chemical_formula_sum            'C21 H14 N4 O2'
_chemical_formula_weight         354.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-10-16 deposited with the CCDC.	2019-03-12 downloaded from the CCDC.
;
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_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_c                   9.52947(11)
_cell_measurement_reflns_used    19820
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.8950
_cell_measurement_theta_min      2.5430
_cell_volume                     1683.16(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29491
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.003
_diffrn_reflns_theta_min         2.526
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0334P)^2^+0.2498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                2963
_reflns_number_total             3038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00716_si_004.cif
_cod_data_source_block           r7
_cod_original_cell_volume        1683.17(3)
_cod_database_code               4033675
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              17768
_shelx_hkl_checksum              24675