NaH Promoted One-Pot Tandem Reactions of 3-(1-Alkynyl) Chromones to Form 2-Nitrogen-Substituted Xanthones
Duan, Wen-Di; Zhang, Yu-Fang; Hu, Youhong; ACS Omega 5 (2020) 13454–13461; doi:10.1021/acsomega.0c01930

data_1558131
_publ_section_title
;
 NaH Promoted One-Pot Tandem Reactions of 3-(1-Alkynyl) Chromones to Form
 2-Nitrogen-Substituted Xanthones
;
_journal_issue                   22
_journal_name_full               'ACS Omega'
_journal_page_first              13454
_journal_page_last               13461
_journal_paper_doi               10.1021/acsomega.0c01930
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C25 H17 Cl N2 O5, C3 H7'
_chemical_formula_sum            'C28 H24 Cl N2 O5'
_chemical_formula_weight         503.94
_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_Hall           '-P 4a'
_space_group_name_H-M_alt        'P 4/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.429(2)
_cell_length_b                   26.429(2)
_cell_length_c                   7.8670(7)
_cell_measurement_reflns_used    4296
_cell_measurement_temperature    110
_cell_measurement_theta_max      24.777
_cell_measurement_theta_min      2.439
_cell_volume                     5495.0(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      110.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1201
_diffrn_reflns_av_unetI/netI     0.1197
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18173
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.180
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1038 before and 0.0826 after correction. The Ratio of minimum to maximum transmission is 0.5840. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
TITL 22019030_0m_a.res in P4/n
CELL   26.4290   26.4290    7.8670     90.00     90.00     90.00
SPGR P4/n
C101 0.648 0.817 0.120 !       3.48 eA-3
C102 0.750 0.748 0.469 !       2.93 eA-3
C103 0.751 0.844 0.029 !       2.84 eA-3
C104 0.250 0.246 0.438 !       2.47 eA-3
C105 0.330 0.329 0.041 !       1.91 eA-3
C106 0.756 0.727 0.676 !       1.64 eA-3
C107 0.728 0.673 0.959 !       1.18 eA-3
C108 0.187 0.237 0.942 !       1.11 eA-3
C109 0.728 0.794 0.292 !       0.98 eA-3
C110 0.296 0.305 0.127 !       0.97 eA-3
C111 0.187 0.236 0.033 !       0.97 eA-3
C112 0.274 0.247 0.649 !       0.96 eA-3
C113 0.286 0.280 0.243 !       0.96 eA-3
C114 0.787 0.698 0.186 !       0.86 eA-3
C115 0.787 0.820 0.216 !       0.85 eA-3
C116 0.301 0.222 0.154 !       0.85 eA-3
C117 0.750 0.749 0.219 !       0.85 eA-3
Q118 0.796 0.387 0.930 !       0.82 eA-3
C119 0.208 0.263 0.782 !       0.82 eA-3
C120 0.360 0.169 0.105 !       0.79 eA-3
C121 0.180 0.218 0.829 !       0.77 eA-3
C122 0.712 0.801 0.969 !       0.75 eA-3
C123 0.749 0.689 0.182 !       0.75 eA-3
C124 0.757 0.788 0.787 !       0.74 eA-3
C125 0.796 0.898-0.004 !       0.72 eA-3
C126 0.353 0.226 0.787 !       0.70 eA-3
C127 0.704 0.779 0.099 !       0.69 eA-3
Q128 0.841 0.703 0.814 !       0.65 eA-3
C129 0.776 0.667 0.898 !       0.65 eA-3
C130 0.274 0.237 0.080 !       0.64 eA-3
Q131 0.831 0.743 0.812 !       0.64 eA-3
Q132 0.808 0.900 0.937 !       0.64 eA-3
Q133 0.836 0.773 0.389 !       0.63 eA-3
Q134 0.189 0.313 0.281 !       0.60 eA-3
Q135 0.299 0.383 0.141 !       0.59 eA-3
Q136 0.704 0.611 0.145 !       0.58 eA-3
C137 0.750 0.746 0.812 !       0.58 eA-3
Q138 0.830 0.667 0.810 !       0.58 eA-3
Q139 0.640 0.800 0.285 !       0.54 eA-3
Q140 0.531 0.275 0.273 !       0.54 eA-3
Q141 0.636 0.662 0.281 !       0.53 eA-3
Q142 0.383 0.272 0.098 !       0.53 eA-3
C143 0.802 0.796 0.354 !       0.53 eA-3
Q144 0.626 0.970 0.065 !       0.53 eA-3
Q145 0.359 0.573 0.122 !       0.53 eA-3
Q146 0.121 0.766 0.129 !       0.52 eA-3
Q147 0.507 0.049 0.382 !       0.52 eA-3
Q148 0.595 0.426 0.427 !       0.52 eA-3
Q149 0.901 0.411 0.436 !       0.51 eA-3
;
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0746
_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^)+(0.0992P)^2^+5.7602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.2393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2584
_reflns_number_total             4844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01930_si_001.cif
_cod_data_source_block           22019030_0m_sq
_cod_original_cell_volume        5495.1(11)
_cod_original_sg_symbol_H-M      'P 4/n'
_cod_database_code               1558131
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C29(H29A,H29B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C20(H20), C17(H17), C13(H13), C2(H2), C5(H5), C10(H10), C21(H21),
 C11(H11), C12(H12), C4(H4)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'