Consecutive cross-dehydrogenative C–O and C–N construction for the synthesis of polyarene with AIE properties under electrochemical condition involving oxygen radical species
Zhang, Zhicheng; Wen, Linzi; Xu, Shihai; Tang, Yu; Cao, Xiaohui; Feng, Pengju; Green Chemistry 25 (2023) 2287–2292; doi:10.1039/D3GC00124E

data_7246321
_publ_section_title
;
 Consecutive cross-dehydrogenative C--O and C--N construction for the
 synthesis of polyarene with AIE properties under electrochemical
 condition involving oxygen radical species
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2287
_journal_page_last               2292
_journal_paper_doi               10.1039/D3GC00124E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C31 H22 N4 O4 S2'
_chemical_formula_sum            'C31 H22 N4 O4 S2'
_chemical_formula_weight         578.64
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-17 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                97.245(2)
_cell_angle_beta                 100.734(2)
_cell_angle_gamma                116.704(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3322(2)
_cell_length_b                   10.7423(2)
_cell_length_c                   14.3583(2)
_cell_measurement_reflns_used    7446
_cell_measurement_temperature    298.06(10)
_cell_measurement_theta_max      73.5920
_cell_measurement_theta_min      3.2280
_cell_volume                     1358.21(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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      air
_diffrn_ambient_temperature      298.06(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.965
_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    -42.00  17.00   0.50    0.50    --    0.00 -57.00 -90.00  118
  2  \w    -17.00  29.00   0.50    0.50    --    0.00  19.00-120.00   92
  3  \w    -59.00  28.00   0.50    0.50    --    0.00 -77.00   0.00  174
  4  \w     57.00  83.00   0.50    0.50    --    0.00  19.00-120.00   52
  5  \w    -89.00 -51.00   0.50    0.50    --    0.00 -57.00 -90.00   76
  6  \w    -18.00   8.00   0.50    0.50    --    0.00  57.00 -30.00   52
  7  \w     91.00 116.00   0.50    0.50    --   95.20 -82.00-120.00   50
  8  \w     10.00 103.00   0.50    0.50    --   95.20 -30.00 150.00  186
  9  \w     10.00  43.00   0.50    0.50    --   95.20 -82.00  60.00   66
 10  \w     48.00 121.00   0.50    0.50    --   95.20 -77.00 -60.00  146
 11  \w     73.00  98.00   0.50    0.50    --   95.20 -82.00 -60.00   50
 12  \w      6.00  32.00   0.50    0.50    --   95.20 -77.00 -60.00   52
 13  \w      9.00 117.00   0.50    0.50    --   95.20 -61.00  60.00  216
 14  \w     34.00 118.00   0.50    0.50    --   95.20 -61.00-180.00  168
 15  \w      6.00 112.00   0.50    0.50    --   95.20 -30.00-120.00  212
 16  \w     11.00  48.00   0.50    0.50    --   95.20 -82.00-180.00   74
 17  \w     79.00 185.00   0.50    0.50    --   95.20  15.00   0.00  212
 18  \w     88.00 119.00   0.50    0.50    --   95.20 -82.00   0.00   62
 19  \w     57.00 116.00   0.50    0.50    --   95.20 -82.00-180.00  118
 20  \w     76.00 111.00   0.50    0.50    --   95.20 -45.00 -60.00   70
 21  \w     44.00  70.00   0.50    0.50    --   95.20 -82.00   0.00   52
 22  \w     20.00  46.00   0.50    0.50    --   95.20 -82.00 -60.00   52
 23  \w     12.00  90.00   0.50    0.50    --   95.20 -45.00  60.00  156
 24  \w     80.00 106.00   0.50    0.50    --   95.20 -82.00 120.00   52
 25  \w     50.00  75.00   0.50    0.50    --   95.20 -82.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1043824000
_diffrn_orient_matrix_UB_12      0.1020063000
_diffrn_orient_matrix_UB_13      0.0994794000
_diffrn_orient_matrix_UB_21      -0.0704321000
_diffrn_orient_matrix_UB_22      -0.1222037000
_diffrn_orient_matrix_UB_23      0.0510636000
_diffrn_orient_matrix_UB_31      0.1194347000
_diffrn_orient_matrix_UB_32      -0.0446566000
_diffrn_orient_matrix_UB_33      -0.0120316000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13425
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.179
_diffrn_reflns_theta_min         3.226
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (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    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.083
_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     373
_refine_ls_number_reflns         5313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0683
_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^)+(0.1409P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1977
_refine_ls_wR_factor_ref         0.2069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4260
_reflns_number_total             5313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc00124e2.cif
_cod_data_source_block           zzc-1
_cod_depositor_comments
;
         Adding full bibliography for 7246321.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C10.33 H7.33 N1.33 O1.33 S0.67'
_cod_original_formula_weight         192.88
_cod_original_formula_moiety         '0.33(C31 H22 N4 O4 S2)'
_cod_original_formula_units_Z            6
_cod_database_code               7246321
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.52
_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 C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C16(H16),
 C19(H19), C20(H20), C21(H21), C27(H27), C28(H28), C29(H29), C30(H30)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 3.453
_oxdiff_exptl_absorpt_empirical_full_min 0.342