Synthesis of 4-arylamino-3-(trifluoromethyl)pyridazines and pyridazino[3,4-b]quinoxalines (as by-products) from 3-aroylmethyl-2-(trifluoromethyl)quinoxalines and hydrazine hydrate
Sosnovskikh, Vyacheslav Y.; Safrygin, Alexander V.; Irgashev, Roman A.; Ezhikova, Marina A.; Kodess, Mikhail I.; RSC Advances 6 (2016) 30056–; doi:10.1039/C5RA27032D

data_7236043
_publ_section_title
;
 Synthesis of 4-arylamino-3-(trifluoromethyl)pyridazines and
 pyridazino[3,4-b]quinoxalines (as by-products) from
 3-aroylmethyl-2-(trifluoromethyl)quinoxalines and hydrazine hydrate
;
_journal_issue                   36
_journal_name_full               'RSC Advances'
_journal_page_first              30056
_journal_paper_doi               10.1039/C5RA27032D
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         '1(C17 H13 F3 N4 O)'
_chemical_formula_sum            'C17 H13 F3 N4 O'
_chemical_formula_weight         346.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-30
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-11-20 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                66.933(4)
_cell_angle_beta                 67.968(4)
_cell_angle_gamma                89.570(3)
_cell_formula_units_Z            8
_cell_length_a                   14.1362(7)
_cell_length_b                   14.3909(5)
_cell_length_c                   18.0057(8)
_cell_measurement_reflns_used    8277
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      30.2670
_cell_measurement_theta_min      2.4290
_cell_volume                     3081.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.8656
_diffrn_measurement_details
;
  1 omega  -21.00   17.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000  -60.0000 38

  2 omega  -30.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920  -19.0000   60.0000 89

  3 omega  -41.00   52.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920  -19.0000  -30.0000 93

  4 omega  -90.00  -46.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  178.0000  -30.0000 44

  5 omega   -7.00   19.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000  -30.0000 26

  6 omega  -10.00   15.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6362 -117.0000   78.2004 25

  7 omega   14.00   65.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362  -99.0000 -180.0000 51

  8 omega  -34.00   36.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362  -57.0000 -120.0000 70

  9 omega   49.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1362  178.0000   30.0000 37
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0218562000
_diffrn_orient_matrix_UB_12      -0.0487284000
_diffrn_orient_matrix_UB_13      0.0358850000
_diffrn_orient_matrix_UB_21      -0.0399888000
_diffrn_orient_matrix_UB_22      -0.0036496000
_diffrn_orient_matrix_UB_23      -0.0139725000
_diffrn_orient_matrix_UB_31      0.0305554000
_diffrn_orient_matrix_UB_32      -0.0236856000
_diffrn_orient_matrix_UB_33      -0.0266278000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33672
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.93
_diffrn_reflns_theta_min         2.03
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1001
_refine_ls_number_reflns         16899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.0490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                11789
_reflns_number_total             16899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra27032d2.cif
_cod_data_source_block           exp_266
_cod_original_cell_volume        3081.9(2)
_cod_database_code               7236043
_chemical_oxdiff_formula         'C10 N4 H5'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22