Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF<sub>3</sub>SO<sub>3</sub>H: Synthesis of ( Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism.
Golushko, Andrei A.; Sandzhieva, Maria A.; Ivanov, Alexander Yu; Boyarskaya, Irina A.; Khoroshilova, Olesya V.; Barkov, Alexey Yu; Vasilyev, Aleksander V.; The Journal of organic chemistry 83 (2018) 10142–10157; doi:10.1021/acs.joc.8b01406

data_4035036
_publ_section_title
;
 Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the
 Superacid CF<sub>3</sub>SO<sub>3</sub>H: Synthesis of (
 Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the
 Reaction Mechanism.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10142
_journal_page_last               10157
_journal_paper_doi               10.1021/acs.joc.8b01406
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H12 F3 N O'
_chemical_formula_sum            'C15 H12 F3 N O'
_chemical_formula_weight         279.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.168(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.01791(18)
_cell_length_b                   9.1748(3)
_cell_length_c                   14.1441(6)
_cell_measurement_reflns_used    5436
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.8870
_cell_measurement_theta_min      3.6590
_cell_volume                     640.94(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1048
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -76.00   49.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621    0.0000 -180.0000 125

  2 omega  -99.00  -50.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621 -178.0000   90.0000 49

  3 omega  -99.00  -73.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621 -178.0000  -90.0000 26

  4 omega   62.00   95.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558 -151.0000 -151.0000 33

  5 omega  -60.00   38.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621   19.0000   60.0000 98

  6 omega  -95.00  -66.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621 -178.0000    0.0000 29

  7 omega    5.00   63.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  -99.0000  -90.0000 58

  8 omega   38.00   65.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  -99.0000   30.0000 27

  9 omega  -24.00    1.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  -99.0000   30.0000 25

 10 omega  -23.00    2.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -38.0000 -120.0000 25

 11 omega   15.00   44.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   38.0000  150.0000 29

 12 omega  -45.00   50.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621    0.0000  -90.0000 95

 13 omega   -6.00   87.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   77.0000 -120.0000 93

 14 omega   -6.00   67.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   77.0000    0.0000 73

 15 omega   35.00   77.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000   30.0000 42

 16 omega   -6.00   92.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   77.0000  120.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0045571000
_diffrn_orient_matrix_UB_12      0.0595317000
_diffrn_orient_matrix_UB_13      0.0316383000
_diffrn_orient_matrix_UB_21      0.0223648000
_diffrn_orient_matrix_UB_22      -0.0483931000
_diffrn_orient_matrix_UB_23      0.0397248000
_diffrn_orient_matrix_UB_31      0.1418294000
_diffrn_orient_matrix_UB_32      0.0095608000
_diffrn_orient_matrix_UB_33      0.0038623000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11746
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.659
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1251 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0342P)^2^+0.1358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0731
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2845
_reflns_number_total             2952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01406_si_012.cif
_cod_data_source_block           7072-9479_vasilev184_2
_cod_database_code               4035036
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'F3 C15 O N'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C10(H10), C9(H9), C8(H8), C16(H16), C12(H12),
 C15(H15), C13(H13), C14(H14)
;
_shelx_res_checksum              68906
_shelx_hkl_checksum              9634
_olex2_submission_special_instructions 'No special instructions were received'