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_7158630
_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         'C34 H25 F3 N2 O5, C H Cl3'
_chemical_formula_sum            'C35 H26 Cl3 F3 N2 O5'
_chemical_formula_weight         717.93
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-09
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-01-11 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.762(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.784(3)
_cell_length_b                   18.643(2)
_cell_length_c                   7.3210(9)
_cell_measurement_reflns_used    3056
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.128
_cell_measurement_theta_min      2.570
_cell_volume                     3245.9(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1314
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            37502
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.071
_diffrn_reflns_theta_max         25.071
_diffrn_reflns_theta_min         2.031
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1516 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.9134.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.0
_exptl_crystal_size_mid          0.0
_exptl_crystal_size_min          0.0
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00105(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5732
_refine_ls_number_restraints     152
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.2177
_refine_ls_R_factor_gt           0.0888
_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^)+(0.0020P)^2^+7.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1706
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2473
_reflns_number_total             5732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00483f2.cif
_cod_data_source_block           fz01
_cod_depositor_comments
'Adding full bibliography for 7158630--7158632.cif.'
_cod_original_cell_volume        3245.9(6)
_cod_database_code               7158630
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Restrained distances
 C35-Cl2
 1.73 with sigma of 0.02
 C35-Cl1
 1.73 with sigma of 0.02
 C35-Cl3
 1.73 with sigma of 0.02
 C35A-Cl1A
 1.73 with sigma of 0.02
 C35A-Cl2A
 1.73 with sigma of 0.02
 C35A-Cl3A
 1.73 with sigma of 0.02
 Cl3-Cl1
 2.6 with sigma of 0.02
 Cl1-Cl3
 2.8 with sigma of 0.02
2. Rigid bond restraints
 Cl3A, C35A, Cl2A, Cl1A, Cl1, Cl3, C35, Cl2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Cl3A \\sim C35A \\sim Cl2A \\sim Cl1A \\sim Cl1 \\sim Cl3 \\sim C35 \\sim Cl2:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(Cl3A) \\sim Ueq, Uanis(C35A) \\sim Ueq, Uanis(Cl2A) \\sim Ueq,
Uanis(Cl1A) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C35) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl2)
\\sim Ueq, Uanis(Cl2A) \\sim Ueq, Uanis(Cl3A) \\sim Ueq, Uanis(C35A) \\sim Ueq,
Uanis(Cl1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: Cl3A(0.5) Cl2A(0.5) Cl1A(0.5) Cl1(0.5) C35A(0.5) H35A(0.5)
 Cl3(0.5) Cl2(0.5) C35(0.5) H35(0.5)
5.a Ternary CH refined with riding coordinates:
 C35A(H35A), C35(H35)
5.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C21(H21), C28(H28), C19(H19), C22(H22), C24(H24), C18(H18), C27(H27),
 C14(H14), C12(H12), C11(H11), C26(H26), C5(H5), C25(H25), C2(H2), C1(H1A),
 C4(H4), C9(H9), C3(H3), C8(H8)
5.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;
_shelx_res_checksum              75710
_olex2_submission_special_instructions 'No special instructions were received'