A bench-stable N-trifluoroacetyl nitrene equivalent for a simple synthesis of 2-trifluoromethyl oxazoles.
Kobayashi, Yusuke; Masakado, Sota; Murai, Takuya; Hamada, Shohei; Furuta, Takumi; Takemoto, Yoshiji; Organic & biomolecular chemistry 19 (2021) 6628–6632; doi:10.1039/d1ob00947h

data_7158166
_publ_section_title
;
 A bench-stable N-trifluoroacetyl nitrene equivalent for a simple
 synthesis of 2-trifluoromethyl oxazoles.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6628
_journal_page_last               6632
_journal_paper_doi               10.1039/d1ob00947h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C8 H4 F3 I N2 O3'
_chemical_formula_sum            'C8 H4 F3 I N2 O3'
_chemical_formula_weight         360.03
_chemical_melting_point          118.0(10)
_chemical_name_systematic        SM569
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-12
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_audit_update_record
;
2021-04-27 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.298(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9637(2)
_cell_length_b                   20.0442(7)
_cell_length_c                   10.3335(4)
_cell_measurement_reflns_used    4927
_cell_measurement_temperature    93
_cell_measurement_theta_max      72.8460
_cell_measurement_theta_min      4.4010
_cell_volume                     1008.19(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_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_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.969
_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    -88.00  90.00   0.50    0.50    --    0.90  29.00 120.00  356
  2  \w    -84.00 -38.00   0.50    1.04    --    5.00  60.00   0.00   92
  3  \w   -188.00 -35.00   0.50    1.04    --  -98.40  57.00  90.00  306
  4  \w   -188.00 -35.00   0.50    1.04    --  -98.40  57.00  60.00  306
  5  \w   -188.00  -9.00   0.50    1.04    --  -98.40  43.00 150.00  358
  6  \w   -188.00 -35.00   0.50    1.04    --  -98.40  57.00  60.00  306
  7  \w   -188.00 -38.00   0.50    1.04    --  -98.40  60.00 150.00  300
  8  \w   -188.00 -38.00   0.50    1.04    --  -98.40  60.00   0.00  300
  9  \w    -90.00 -38.00   0.50    0.50    --   -0.90  60.00  90.00  104
 10  \w   -188.00-110.00   0.50    1.04    --  -98.40   0.00 150.00  156
 11  \w   -188.00  -9.00   0.50    1.04    --  -98.40   0.00   0.00  358
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0165057000
_diffrn_orient_matrix_UB_12      -0.0653566000
_diffrn_orient_matrix_UB_13      0.0796123000
_diffrn_orient_matrix_UB_21      -0.0346352000
_diffrn_orient_matrix_UB_22      -0.0404306000
_diffrn_orient_matrix_UB_23      -0.1289541000
_diffrn_orient_matrix_UB_31      0.3142264000
_diffrn_orient_matrix_UB_32      -0.0010419000
_diffrn_orient_matrix_UB_33      0.0115457000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9201
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.260
_diffrn_reflns_theta_min         4.412
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    25.461
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
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    2.372
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_preparation       condensation
_exptl_crystal_recrystallization_method pyridine-ether
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         3.497
_refine_diff_density_min         -3.623
_refine_diff_density_rms         0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0641
_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^)+(0.1324P)^2^+3.8932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.1789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1908
_reflns_number_total             1959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00947h2.cif
_cod_data_source_block           exp_218
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '117-119' was changed to
'118.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158166.cif.
;
_cod_database_code               7158166
_chemical_oxdiff_formula         'C20 H16 F12 I4 N20 O12 '
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C4(H4), C3(H3)
;
_shelx_res_checksum              93317
_shelx_shelxl_version_number     2016/6
_olex2_exptl_crystal_mounting_method loop
_olex2_submission_original_sample_id SM569
_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 8.300
_oxdiff_exptl_absorpt_empirical_full_min 0.555