4-Methyl/Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones Synthesis: Mechanistic Pathway Study and Single-Crystal X-ray Analysis of the Intermediates
Sarhan, Ahmed A. M.; Haukka, Matti; Barakat, Assem; Soliman, Saied M.; Boraei, Ahmed T. A.; Sopaih, Manar; Salama, Eid E.; Crystals 13 (2023) 1537–; doi:10.3390/cryst13111537

data_1570247
_publ_section_title
;
 4-Methyl/Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones Synthesis:
 Mechanistic Pathway Study and Single-Crystal X-ray Analysis of the
 Intermediates
;
_journal_issue                   11
_journal_name_full               Crystals
_journal_page_first              1537
_journal_paper_doi               10.3390/cryst13111537
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C18 H14 N4 O'
_chemical_formula_sum            'C18 H14 N4 O'
_chemical_formula_weight         302.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.04710(10)
_cell_length_b                   12.5114(3)
_cell_length_c                   22.2915(5)
_cell_measurement_reflns_used    4611
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.4700
_cell_measurement_theta_min      3.9420
_cell_volume                     1407.63(5)
_computing_cell_refinement
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_collection
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_molecular_graphics
'CrystaMaker X (CrystalMaker Software ltd., 2021)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\f scans and \w scans with \k offset'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10944
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.765
_diffrn_reflns_theta_min         3.966
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1024 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0371P)^2^+0.1092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0794
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2683
_reflns_number_total             2929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nd10.cif
_cod_data_source_block           nd10
_cod_database_code               1570247
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.871
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              20757
_shelx_hkl_checksum              8996