Synthesis of Triarylmethanes by Decarbonylation of 3, 3-Diaryl Benzofuranones.
Tang, Zhi; Peng, Lingteng; Yuan, Yu; Li, Tianjing; Qiu, Renhua; Kambe, Nobuaki; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03433

data_4038166
_publ_section_title
;
 Synthesis of Triarylmethanes by Decarbonylation of 3, 3-Diaryl
 Benzofuranones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03433
_journal_year                    2020
_chemical_formula_moiety         'C28 H28 N2 O2'
_chemical_formula_sum            'C28 H28 N2 O2'
_chemical_formula_weight         424.52
_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             2018-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.144(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6186(5)
_cell_length_b                   11.8426(7)
_cell_length_c                   18.1021(10)
_cell_measurement_reflns_used    3987
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.4930
_cell_measurement_theta_min      2.4610
_cell_volume                     2459.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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    -44.00  64.00   1.00    3.00    --  -11.59  77.00  60.00  108
  2  \w    -18.00  57.00   1.00    3.00    --   11.74  77.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0167696000
_diffrn_orient_matrix_UB_12      0.0571990000
_diffrn_orient_matrix_UB_13      -0.0028113000
_diffrn_orient_matrix_UB_21      -0.0323292000
_diffrn_orient_matrix_UB_22      0.0027111000
_diffrn_orient_matrix_UB_23      -0.0366560000
_diffrn_orient_matrix_UB_31      -0.0499438000
_diffrn_orient_matrix_UB_32      0.0174341000
_diffrn_orient_matrix_UB_33      0.0150303000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10081
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.063
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0597P)^2^+1.0336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1333
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3439
_reflns_number_total             4246
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03433_si_002.cif
_cod_data_source_block           tzr40
_cod_database_code               4038166
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 96.77
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C7(H7), C8(H8), C21(H21), C18(H18), C12(H12), C20(H20), C3(H3),
 C16(H16), C13(H13), C14(H14), C4(H4), C15(H15), C5(H5)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C27(H27A,H27B,
 H27C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.779