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_7158632
_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         'C22 H15 F3 N2 O4'
_chemical_formula_sum            'C22 H15 F3 N2 O4'
_chemical_formula_weight         428.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-11 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.751(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.4017(14)
_cell_length_b                   10.6516(5)
_cell_length_c                   14.9143(8)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.763
_cell_measurement_theta_min      2.353
_cell_volume                     4029.0(4)
_computing_cell_refinement       lb20201022
_computing_data_reduction        lb20201022
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            63913
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.064
_diffrn_reflns_theta_max         25.064
_diffrn_reflns_theta_min         2.074
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.9320.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7127
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0671P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                6492
_reflns_number_total             7127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00483f2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7158630--7158632.cif.'
_cod_database_code               7158632
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_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:
 C33(H33A,H33B), C48(H48A,H48B)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C32(H32), C34(H34), C35(H35), C41(H41), C42(H42), C45(H45),
 C46(H46), C47(H47), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54),
  C56(H56), C57(H57), C58(H58), C60(H60), C61(H61)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              12541
_olex2_submission_special_instructions 'No special instructions were received'