Cascade Oxidation/Halogenoaminocyclization Reaction of Trifluoromethylated Homoallylic N-Acylhydrazines: Metal-free Synthesis of CF<sub>3</sub>-Substituted Pyrazolines.
Wang, Yuxiang; Wang, Ke-Hu; Su, Yingpeng; Yang, Zheng; Wen, Lan; Liu, Lili; Wang, Juanjuan; Huang, Danfeng; Hu, Yulai; The Journal of organic chemistry 83 (2018) 939–950; doi:10.1021/acs.joc.7b02934

data_4033322
_publ_section_title
;
 Cascade Oxidation/Halogenoaminocyclization Reaction of
 Trifluoromethylated Homoallylic N-Acylhydrazines: Metal-free Synthesis of
 CF<sub>3</sub>-Substituted Pyrazolines.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              939
_journal_page_last               950
_journal_paper_doi               10.1021/acs.joc.7b02934
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C10 H8 F3 I N2 O2'
_chemical_formula_sum            'C10 H8 F3 I N2 O2'
_chemical_formula_weight         372.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.471(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7410(6)
_cell_length_b                   5.5915(4)
_cell_length_c                   25.644(3)
_cell_measurement_reflns_used    1180
_cell_measurement_temperature    295.19(10)
_cell_measurement_theta_max      23.9840
_cell_measurement_theta_min      3.9650
_cell_volume                     1247.65(19)
_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    '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      295.19(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -45.00   45.00   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  120.0000 60

  2 omega   -8.00   92.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000   90.0000 67

  3 omega   19.00   53.50   1.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000 -120.0000 23
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0110260000
_diffrn_orient_matrix_UB_12      -0.0036844000
_diffrn_orient_matrix_UB_13      0.0277938000
_diffrn_orient_matrix_UB_21      -0.0794893000
_diffrn_orient_matrix_UB_22      0.0215468000
_diffrn_orient_matrix_UB_23      0.0012053000
_diffrn_orient_matrix_UB_31      -0.0141193000
_diffrn_orient_matrix_UB_32      -0.1248351000
_diffrn_orient_matrix_UB_33      -0.0006336000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4386
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.73
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55721
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0294P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                1660
_reflns_number_total             2449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02934_si_001.cif
_cod_data_source_block           wangyx_150
_cod_depositor_comments
'Adding full bibliography for 4033321--4033322.cif.'
_cod_original_cell_volume        1247.69(18)
_cod_database_code               4033322
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
;
_olex2_date_sample_data_collection 2017-09-22
_olex2_submission_special_instructions 'No special instructions were received'