Synthetic exploration of electrophilic xanthylation via powerful N-xanthylphthalimides
Wang, Shuo; Yang, Liuqing; Liang, Fangcan; Zhong, Yu; Liu, Xueru; Wang, Qingling; Zhu, Dianhu; Chemical Science 14 (2023) 9197–9206; doi:10.1039/D3SC03194B

data_1569597
_publ_section_title
;
 Synthetic exploration of electrophilic xanthylation via powerful
 N-xanthylphthalimides
;
_journal_issue                   34
_journal_name_full               'Chemical Science'
_journal_page_first              9197
_journal_page_last               9206
_journal_paper_doi               10.1039/D3SC03194B
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C11 H9 N O3 S2'
_chemical_formula_sum            'C11 H9 N O3 S2'
_chemical_formula_weight         267.31
_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             2023-03-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2023-03-22 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.271(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3474(8)
_cell_length_b                   14.3530(10)
_cell_length_c                   8.1480(6)
_cell_measurement_reflns_used    8568
_cell_measurement_temperature    260.00
_cell_measurement_theta_max      56.927
_cell_measurement_theta_min      2.679
_cell_volume                     1194.30(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      260.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17614
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.106
_diffrn_reflns_theta_min         3.766
_diffrn_source_current           2.86
_diffrn_source_power             0.19985679999999997
_diffrn_source_voltage           69.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.650
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.4662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1586 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.6206.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2442
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0738P)^2^+0.1734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1846
_reflns_number_total             2442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03194b2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1569597.cif.'
_cod_database_code               1569597
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.742
_shelx_estimated_absorpt_t_min   0.619
_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
2. Rigid bond restraints
 S2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C7(H7), C8(H8)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              21372
_olex2_submission_special_instructions 'No special instructions were received'