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_4035039
_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_formula_moiety         'C19 H20 F3 N O'
_chemical_formula_sum            'C19 H20 F3 N O'
_chemical_formula_weight         335.36
_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
_audit_creation_date             2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                104.204(9)
_cell_angle_beta                 93.568(7)
_cell_angle_gamma                97.731(7)
_cell_formula_units_Z            2
_cell_length_a                   6.4856(5)
_cell_length_b                   10.5126(11)
_cell_length_c                   13.3256(13)
_cell_measurement_reflns_used    1395
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.5810
_cell_measurement_theta_min      3.4960
_cell_volume                     868.46(15)
_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 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -91.00   -1.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -57.0000  -60.0000 90

  2 omega  -44.00   47.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   57.0000   90.0000 91

  3 omega  -19.00    6.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000   90.0000 25

  4 omega  -21.00   11.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000  -30.0000 32

  5 omega  -91.00  -25.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -77.0000 -180.0000 66

  6 omega  -25.00   20.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000 -150.0000 45

  7 omega  -43.00    7.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -19.0000 -180.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0858260000
_diffrn_orient_matrix_UB_12      0.0258351000
_diffrn_orient_matrix_UB_13      0.0236069000
_diffrn_orient_matrix_UB_21      -0.0050417000
_diffrn_orient_matrix_UB_22      -0.0471615000
_diffrn_orient_matrix_UB_23      0.0301346000
_diffrn_orient_matrix_UB_31      0.0700748000
_diffrn_orient_matrix_UB_32      0.0455117000
_diffrn_orient_matrix_UB_33      0.0397408000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.872
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88598
_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    1.282
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.345
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.0976
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1664P)^2^+0.6332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2832
_refine_ls_wR_factor_ref         0.3317
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2160
_reflns_number_total             3965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01406_si_003.cif
_cod_data_source_block           103-7072-7940_93
_cod_original_cell_volume        868.47(14)
_cod_database_code               4035039
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'F3 N O C17'
_reflns_odcompleteness_completeness 98.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C11(H11), C13(H13), C14(H14), C17(H17)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              3373
_shelx_hkl_checksum              6726
_olex2_date_sample_data_collection 2017-11-18
_olex2_submission_special_instructions 'No special instructions were received'