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_4035042
_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         'C23 H28 F3 N O'
_chemical_formula_sum            'C23 H28 F3 N O'
_chemical_formula_weight         391.46
_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             2017-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                112.401(6)
_cell_angle_beta                 111.794(8)
_cell_angle_gamma                90.343(5)
_cell_formula_units_Z            4
_cell_length_a                   11.3298(9)
_cell_length_b                   14.7085(8)
_cell_length_c                   14.7900(12)
_cell_measurement_reflns_used    6521
_cell_measurement_temperature    100(5)
_cell_measurement_theta_max      30.8460
_cell_measurement_theta_min      3.3970
_cell_volume                     2084.4(3)
_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(5)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -16.00   10.00   1.0000  116.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -83.0000  162.0000 26

  2 omega  -77.00  -51.00   1.0000  116.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000   90.0000 26

  3 omega  -35.00   -9.00   1.0000  116.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000   30.0000 26

  4 omega  -15.00   64.00   1.0000  116.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -60.0000 79

  5 omega    6.00   91.00   1.0000  116.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000 -150.0000 85

  6 omega   20.00   65.00   1.0000  116.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   90.0000 45

  7 omega  -41.00   40.00   1.0000  116.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -57.0000  -30.0000 81

  8 omega  -20.00   95.00   1.0000  116.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   19.0000  150.0000 115
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0298033000
_diffrn_orient_matrix_UB_12      -0.0144349000
_diffrn_orient_matrix_UB_13      -0.0367190000
_diffrn_orient_matrix_UB_21      -0.0484654000
_diffrn_orient_matrix_UB_22      -0.0430747000
_diffrn_orient_matrix_UB_23      -0.0336274000
_diffrn_orient_matrix_UB_31      -0.0380324000
_diffrn_orient_matrix_UB_32      0.0272109000
_diffrn_orient_matrix_UB_33      -0.0271450000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9561
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.647
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95173
_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    1.247
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         9561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.001
_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^+0.2960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7204
_reflns_number_total             9561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01406_si_004.cif
_cod_data_source_block           ca-101
_cod_database_code               4035042
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C23 F3 N O'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8623(18)
 0.1377(18)
2. 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
3.a Ternary CH refined with riding coordinates:
 C3(H3), C11(H11)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C23(H23), C25(H25), C1M(H1M)
3.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC), C1D(H1DA,H1DB,
 H1DC), C1E(H1EA,H1EB,H1EC), C1F(H1FA,H1FB,H1FC), C1G(H1GA,H1GB,H1GC), C1I(H1IA,
 H1IB,H1IC), C1J(H1JA,H1JB,H1JC), C1K(H1KA,H1KB,H1KC), C1L(H1LA,H1LB,H1LC),
 C1N(H1NA,H1NB,H1NC), C1O(H1OA,H1OB,H1OC), C1P(H1PA,H1PB,H1PC), C1Q(H1QA,H1QB,
 H1QC), C1R(H1RA,H1RB,H1RC)
3.d Idealised tetrahedral OH refined as rotating group:
 O7(H7), O8(H8)
;
_shelx_res_checksum              97090
_shelx_hkl_checksum              53951
_olex2_submission_special_instructions 'No special instructions were received'