Synthesis of α-trifluoromethyl ethanone oximes via the three-component reaction of aryl-substituted ethylenes, tert-butyl nitrite, and the Langlois reagent
Lu, Kui; Wei, Xianfu; Li, Quan; Li, Yuxuan; Ji, Liangshuo; Hua, Erbing; Dai, Yujie; Zhao, Xia; Organic Chemistry Frontiers 6 (2019) 3766–; doi:10.1039/C9QO00940J

data_1555127
_publ_section_title
;
 Synthesis of \a-trifluoromethyl ethanone oximes via the three-component
 reaction of aryl-substituted ethylenes, tert-butyl nitrite, and the
 Langlois reagent
;
_journal_issue                   22
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3766
_journal_paper_doi               10.1039/C9QO00940J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C13 H10 F3 N O'
_chemical_formula_sum            'C13 H10 F3 N O'
_chemical_formula_weight         253.22
_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
_audit_creation_date             2018-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2019-07-25 deposited with the CCDC.	2019-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                91.045(13)
_cell_angle_beta                 91.275(14)
_cell_angle_gamma                101.201(13)
_cell_formula_units_Z            2
_cell_length_a                   5.0942(9)
_cell_length_b                   9.6532(13)
_cell_length_c                   11.935(2)
_cell_measurement_reflns_used    1111
_cell_measurement_temperature    293.6(3)
_cell_measurement_theta_max      26.3190
_cell_measurement_theta_min      2.1880
_cell_volume                     575.43(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.6(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -82.00  12.00   1.00   17.16    --  -11.24 -57.00  60.00   94
  2  \w    -76.00  16.00   1.00   17.16    --  -11.24 -77.00 -60.00   92
  3  \w    -38.00  56.00   1.00   17.16    --  -11.24  57.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1167167000
_diffrn_orient_matrix_UB_12      -0.0115745000
_diffrn_orient_matrix_UB_13      0.0325619000
_diffrn_orient_matrix_UB_21      -0.0035331000
_diffrn_orient_matrix_UB_22      0.0730267000
_diffrn_orient_matrix_UB_23      -0.0016864000
_diffrn_orient_matrix_UB_31      -0.0807820000
_diffrn_orient_matrix_UB_32      -0.0121172000
_diffrn_orient_matrix_UB_33      -0.0497212000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3660
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         1.707
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.018(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1682
_refine_ls_R_factor_gt           0.0938
_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^)+(0.1250P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2251
_refine_ls_wR_factor_ref         0.2822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                875
_reflns_number_total             2014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00940j2.cif
_cod_data_source_block           a181019a
_cod_original_cell_volume        575.46(16)
_cod_database_code               1555127
_reflns_odcompleteness_completeness 99.92
_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
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C9(H9), C4(H4), C7(H7), C5(H5), C6(H6)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-10-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.455
_oxdiff_exptl_absorpt_empirical_full_min 0.462