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_4035037
_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         'C15 H12 Cl3 N O'
_chemical_formula_sum            'C15 H12 Cl3 N O'
_chemical_formula_weight         328.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 96.073(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5726(4)
_cell_length_b                   16.6112(8)
_cell_length_c                   15.7310(10)
_cell_measurement_reflns_used    3255
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.8180
_cell_measurement_theta_min      3.5870
_cell_volume                     1448.01(16)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   61.00   96.00   1.0000   85.4000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000   90.0000 35

  2 omega  -41.00   94.00   1.0000   85.4000
omega____ theta____ kappa____ phi______ frames
    -       24.4558    0.0000   60.0000 135

  3 omega  -46.00   17.00   1.0000   85.4000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  -38.0000   30.0000 63

  4 omega  -98.00  -62.00   1.0000   85.4000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621 -178.0000    0.0000 36

  5 omega   37.00   64.00   1.0000   85.4000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000   90.0000 27

  6 omega    8.00   47.00   1.0000   85.4000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   57.0000   30.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1023972000
_diffrn_orient_matrix_UB_12      0.0219131000
_diffrn_orient_matrix_UB_13      -0.0178292000
_diffrn_orient_matrix_UB_21      -0.0567303000
_diffrn_orient_matrix_UB_22      -0.0066561000
_diffrn_orient_matrix_UB_23      0.0377014000
_diffrn_orient_matrix_UB_31      0.0517865000
_diffrn_orient_matrix_UB_32      0.0360447000
_diffrn_orient_matrix_UB_33      0.0177672000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            3323
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.777
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71311
_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    1.507
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0066P)^2^+2.8787P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2971
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01406_si_013.cif
_cod_data_source_block           7072-8997_vasilev-181-3
_cod_original_cell_volume        1448.01(15)
_cod_database_code               4035037
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 Cl3'
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.880
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.881(3)
 0.119(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 C1(H1A)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C7(H7), C8(H8), C10(H10), C4(H4), C5(H5), C6(H6), C13(H13),
 C11(H11), C14(H14)
;
_shelx_res_checksum              24871
_shelx_hkl_checksum              70073
_olex2_date_sample_data_collection 1520256724.15
_olex2_submission_special_instructions 'No special instructions were received'