Transition-metal-free cascade benzannulations for synthesizing 2-hydroxybenzophenones
He, Xue-Wen; Zhou, Wei; Zhang, Min; Tian, Min-Yi; Wang, Hui-Juan; Tian, You-Ping; Liu, Xiong-Li; Organic & Biomolecular Chemistry 18 (2020) 9039–9043; doi:10.1039/D0OB01894E

data_7157784
_publ_section_title
;
 Transition-metal-free cascade benzannulations for synthesizing
 2-hydroxybenzophenones
;
_journal_issue                   44
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              9039
_journal_page_last               9043
_journal_paper_doi               10.1039/D0OB01894E
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C19 H13 N O4'
_chemical_formula_sum            'C19 H13 N O4'
_chemical_formula_weight         319.30
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-12
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.08.16 svn.r3652 for OlexSys, GUI svn.r5895)
;
_audit_update_record
;
2020-03-29 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.001(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.2074(4)
_cell_length_b                   12.9179(9)
_cell_length_c                   27.180(2)
_cell_measurement_reflns_used    2668
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.2030
_cell_measurement_theta_min      3.7550
_cell_volume                     1473.7(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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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  32.00   1.00    1.00    --  -40.98  57.00  90.00   26
  2  \w    -63.00  -9.00   1.00    1.00    --  -40.98  57.00  90.00   54
  3  \w   -107.00 -15.00   1.00    1.00    --  -40.98 -57.00 -60.00   92
  4  \w     29.00  86.00   1.00    1.00    --   40.98-125.00 -90.00   57
  5  \w     29.00  54.00   1.00    1.00    --   40.98-125.00-180.00   25
  6  \w     64.00 117.00   1.00    1.00    --  106.95-125.00  90.00   53
  7  \w     72.00 123.00   1.00    1.00    --  106.95 -45.00 150.00   51
  8  \w     79.00 167.00   1.00    1.00    --  106.95  61.00   0.00   88
  9  \w    116.00 171.00   1.00    1.00    --  106.95 125.00 -30.00   55
 10  \w    104.00 140.00   1.00    1.00    --  106.95  86.00-117.00   36
 11  \w     78.00 165.00   1.00    1.00    --  106.95  61.00 -60.00   87
 12  \w     34.00  63.00   1.00    1.00    --  106.95-125.00  90.00   29
 13  \w     24.00 105.00   1.00    1.00    --  106.95 -94.00 120.00   81
;
_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      -0.0807716500
_diffrn_orient_matrix_UB_12      0.0529833500
_diffrn_orient_matrix_UB_13      0.0061600000
_diffrn_orient_matrix_UB_21      0.0709198500
_diffrn_orient_matrix_UB_22      0.0028747500
_diffrn_orient_matrix_UB_23      0.0537105000
_diffrn_orient_matrix_UB_31      0.1485879500
_diffrn_orient_matrix_UB_32      0.0272552500
_diffrn_orient_matrix_UB_33      -0.0175543000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6110
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.334
_diffrn_reflns_theta_min         3.260
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16827
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0039(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0771
_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^)+(0.1071P)^2^+2.3602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2231
_refine_ls_wR_factor_ref         0.2291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2485
_reflns_number_total             2894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01894e2.cif
_cod_data_source_block           16-1-02
_cod_database_code               7157784
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4A), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19)
;
_shelx_res_checksum              47839
_shelx_hkl_checksum              74088
_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 3.405
_oxdiff_exptl_absorpt_empirical_full_min 0.256