Synthesis of 4-trifluoromethyl pyridazines <i>via</i> annulation of pyridinium ylides with trifluoroacetyl diazoester.
Fang, Zheng; Teng, Yun; Yang, Huilin; Li, Rongxing; Li, Qiuhong; You, Yi; Weng, Zhiqiang; Organic & biomolecular chemistry 20 (2022) 3564–3569; doi:10.1039/d2ob00483f

data_7158631
_publ_section_title
;
 Synthesis of 4-trifluoromethyl pyridazines <i>via</i> annulation of
 pyridinium ylides with trifluoroacetyl diazoester.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3564
_journal_page_last               3569
_journal_paper_doi               10.1039/d2ob00483f
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C24 H13 F3 N6 O2'
_chemical_formula_sum            'C24 H13 F3 N6 O2'
_chemical_formula_weight         474.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-27 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.582(3)
_cell_length_b                   12.447(3)
_cell_length_c                   22.472(5)
_cell_measurement_reflns_used    2636
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.23
_cell_volume                     4358.4(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1742
_diffrn_reflns_av_unetI/netI     0.1298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20284
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.235
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1021 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.8031.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.2218
_refine_ls_R_factor_gt           0.1079
_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^)+(0.0830P)^2^+7.7766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1801
_reflns_number_total             3984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00483f2.cif
_cod_data_source_block           a_pl
_cod_depositor_comments
'Adding full bibliography for 7158630--7158632.cif.'
_cod_database_code               7158631
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.978
_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:
 C072(H07A,H07B)
2.b Aromatic/amide H refined with riding coordinates:
 C00Z(H00Z), C04H(H04H), C05E(H05E), C05K(H05K), C06B(H06B), C06T(H06T),
 C06Z(H06Z), C070(H070)
2.c Idealised Me refined as rotating group:
 C07O(H07C,H07D,H07E)
;
_shelx_res_checksum              93174
_olex2_submission_special_instructions 'No special instructions were received'