One-pot synthesis of 3-trifluoromethylbenzo[b][1,4]oxazines from CF3-imidoyl sulfoxonium ylides with 2-bromophenols
Pan, Mingshi; Tong, Yixin; Qiu, Xiaodong; Zeng, Xiaobao; Xiong, Biao; Chemical Communications  (2022) –; doi:10.1039/D2CC04863A

data_7130886
_publ_section_title
;
 One-pot synthesis of 3-trifluoromethylbenzo[b][1,4]oxazines from
 CF3-imidoyl sulfoxonium ylides with 2-bromophenols
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04863A
_journal_year                    2022
_chemical_formula_moiety         'C19 H12 F3 N O'
_chemical_formula_sum            'C19 H12 F3 N O'
_chemical_formula_weight         327.30
_chemical_melting_point          389.15
_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     direct
_audit_creation_date             2022-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-29 deposited with the CCDC.	2022-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.936(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2901(13)
_cell_length_b                   7.7946(13)
_cell_length_c                   26.574(4)
_cell_measurement_reflns_used    883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.5440
_cell_measurement_theta_min      2.6920
_cell_volume                     1501.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.856
_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      6.00  38.40   0.90   10.00    --   15.49  57.00 -90.00   36
  2  \w    -23.00  22.00   0.90   10.00    --  -16.28 -99.00  90.00   50
  3  \w    -20.00   5.20   0.90   10.00    --  -16.28 -99.00   0.00   28
  4  \w    -84.00  -3.00   0.90   10.00    --  -16.28 -57.00-150.00   90
  5  \w    -82.00 -46.90   0.90   10.00    --  -16.28 -77.00 150.00   39
  6  \w     38.00  87.50   0.90   10.00    --   15.49 178.00 150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0218367000
_diffrn_orient_matrix_UB_12      0.0461294000
_diffrn_orient_matrix_UB_13      -0.0228259000
_diffrn_orient_matrix_UB_21      0.0130992000
_diffrn_orient_matrix_UB_22      -0.0754938000
_diffrn_orient_matrix_UB_23      -0.0140858000
_diffrn_orient_matrix_UB_31      -0.0945419000
_diffrn_orient_matrix_UB_32      -0.0210734000
_diffrn_orient_matrix_UB_33      0.0004468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.1097
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            8471
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.286
_diffrn_reflns_theta_min         2.724
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1837
_refine_ls_R_factor_gt           0.0776
_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^)+(0.0381P)^2^+0.8047P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1566
_reflns_number_total             3506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04863a2.cif
_cod_data_source_block           3ga
_cod_database_code               7130886
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C2(H2), C16(H16), C3(H3), C8(H8), C13(H13), C14(H14), C18(H18),
 C5(H5), C7(H7), C6(H6), C15(H15)
;
_shelx_res_checksum              92591
_shelx_hkl_checksum              9491
_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 1.553
_oxdiff_exptl_absorpt_empirical_full_min 0.673