Rhodium-Catalyzed Merging of 2-Arylquinazolinone and 2,2-Difluorovinyl Tosylate: Diverse Synthesis of Monofluoroolefin Quinazolinone Derivatives.
Wang, Ning; Yang, Qin; Deng, Zhihong; Mao, Xuechun; Peng, Yiyuan; ACS omega 5 (2020) 14635–14644; doi:10.1021/acsomega.0c01344

data_4517767
_publ_section_title
;
 Rhodium-Catalyzed Merging of 2-Arylquinazolinone and 2,2-Difluorovinyl
 Tosylate: Diverse Synthesis of Monofluoroolefin Quinazolinone
 Derivatives.
;
_journal_issue                   24
_journal_name_full               'ACS omega'
_journal_page_first              14635
_journal_page_last               14644
_journal_paper_doi               10.1021/acsomega.0c01344
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C24 H19 F N2 O4 S'
_chemical_formula_sum            'C24 H19 F N2 O4 S'
_chemical_formula_weight         450.47
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                94.192(5)
_cell_angle_beta                 91.254(5)
_cell_angle_gamma                96.483(5)
_cell_formula_units_Z            2
_cell_length_a                   5.8952(4)
_cell_length_b                   8.3803(4)
_cell_length_c                   21.5947(13)
_cell_measurement_reflns_used    5680
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.0220
_cell_measurement_theta_min      3.8850
_cell_volume                     1056.71(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.851
_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 -35.00   1.00    2.49    --  -15.92-178.00 -90.00   53
  2  \w    -51.00  44.00   1.00    2.49    --   16.85 -77.00-180.00   95
  3  \w    -10.00  84.00   1.00    2.49    --   16.85  77.00 -60.00   94
  4  \w    -10.00  84.00   1.00    2.49    --   16.85  77.00  90.00   94
  5  \w    -50.00  34.00   1.00    2.49    --   16.85 -57.00  30.00   84
  6  \w      0.00  84.00   1.00    2.49    --   16.85  57.00  90.00   84
  7  \w    -88.00 -35.00   1.00    2.49    --  -15.92-178.00-180.00   53
  8  \w      0.00  25.00   1.00    2.49    --   16.85  57.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0476276000
_diffrn_orient_matrix_UB_12      -0.0755859000
_diffrn_orient_matrix_UB_13      -0.0143210000
_diffrn_orient_matrix_UB_21      -0.0425832000
_diffrn_orient_matrix_UB_22      -0.0226037000
_diffrn_orient_matrix_UB_23      0.0289474000
_diffrn_orient_matrix_UB_31      -0.1029332000
_diffrn_orient_matrix_UB_32      0.0327772000
_diffrn_orient_matrix_UB_33      -0.0065285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13855
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.474
_diffrn_reflns_theta_min         3.480
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_preparation       'as synthesized'
_exptl_crystal_recrystallization_method 'slow evaporated from DCM'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0587P)^2^+0.2292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4119
_reflns_number_total             4995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01344_si_002.cif
_cod_data_source_block           wn-4
_cod_depositor_comments          'Adding full bibliography for 4517767.cif.'
_cod_database_code               4517767
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.908
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C24(H24a,H24b,H24c)
;
_olex2_date_sample_completion    2019-07-23
_olex2_date_sample_data_collection 2019-07-23
_olex2_date_sample_submission    2019-07-23
_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 1.385
_oxdiff_exptl_absorpt_empirical_full_min 0.457