DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement
Ganai, Ab Majeed; Pathan, Tabasum Khan; Sayyad, Nisar; Kushwaha, Babita; Kushwaha, Narva Deshwar; Tzakos, Andreas G.; Karpoormath, Rajshekhar; RSC Advances 12 (2022) 2102–2106; doi:10.1039/D1RA07749J

data_7244195
_publ_section_title
;
 DBU mediated one-pot synthesis of triazolo triazines via Dimroth type
 rearrangement
;
_journal_issue                   4
_journal_name_full               'RSC Advances'
_journal_page_first              2102
_journal_page_last               2106
_journal_paper_doi               10.1039/D1RA07749J
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C20 H25 N7 O4'
_chemical_formula_sum            'C20 H25 N7 O4'
_chemical_formula_weight         427.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-12-29 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.964(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.320(3)
_cell_length_b                   12.339(3)
_cell_length_c                   15.403(4)
_cell_measurement_reflns_used    7223
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.12
_cell_measurement_theta_min      2.53
_cell_volume                     2022.2(9)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13314
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.173
_diffrn_reflns_theta_min         1.950
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0937 before and 0.0515 after correction.
The Ratio of minimum to maximum transmission is 0.8525.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0522P)^2^+0.6921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3230
_reflns_number_total             3995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra07749j2.cif
_cod_data_source_block           20zs_rk_a2_aldol_ipa_0m
_cod_original_cell_volume        2022.3(9)
_cod_database_code               7244195
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C19(H19A,
 H19B), C18(H18A,H18B), C17(H17A,H17B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              82978
_olex2_submission_special_instructions 'No special instructions were received'