Regioselective intramolecular cyclization of o-alkynyl arylamines with the in situ formation of ArXCl to construct poly-functionalized 3-selenylindoles
Yu, Minhui; Jin, Tao; Wang, Xiaohua; Li, Haohu; Ji, Decai; Yao, Jinzhong; Zeng, Heyang; Shi, Senlei; Xu, Kaimeng; Zhang, Lianpeng; RSC Advances 13 (2023) 6210–6216; doi:10.1039/D3RA00030C

data_7246322
_publ_section_title
;
 Regioselective intramolecular cyclization of o-alkynyl arylamines with
 the in situ formation of ArXCl to construct poly-functionalized
 3-selenylindoles
;
_journal_issue                   9
_journal_name_full               'RSC Advances'
_journal_page_first              6210
_journal_page_last               6216
_journal_paper_doi               10.1039/D3RA00030C
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C27 H21 N O2 S Se'
_chemical_formula_sum            'C27 H21 N O2 S Se'
_chemical_formula_weight         502.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-05-06 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9420(4)
_cell_length_b                   18.6317(17)
_cell_length_c                   20.5632(13)
_cell_measurement_reflns_used    1748
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6150
_cell_measurement_theta_min      4.0820
_cell_volume                     2276.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.871
_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     -1.00  84.00   1.00    4.29    --   16.20  38.00-150.00   85
  2  \w     16.00  72.00   1.00    4.29    --   16.20  19.00 150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0145475000
_diffrn_orient_matrix_UB_12      0.0363563000
_diffrn_orient_matrix_UB_13      -0.0094609000
_diffrn_orient_matrix_UB_21      0.0408612000
_diffrn_orient_matrix_UB_22      0.0114731000
_diffrn_orient_matrix_UB_23      0.0306848000
_diffrn_orient_matrix_UB_31      0.1112041000
_diffrn_orient_matrix_UB_32      0.0005499000
_diffrn_orient_matrix_UB_33      -0.0124635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7248
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.381
_diffrn_reflns_theta_min         2.951
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    13.599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    3.234
_exptl_crystal_F_000             2056
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 967 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0243P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0701
_reflns_Friedel_coverage         0.634
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                3139
_reflns_number_total             5099
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra00030c2.cif
_cod_data_source_block           100-20191125
_cod_depositor_comments
;

2025-01-11
Changing absurd formula for real one (given in _chemical_formula_moiety)
Values such as density and absorption coefficient are surely wrong
                 miguel
;
_cod_original_formula_sum            'C8 H8 N8 O0.25 S8 Se8'
_cod_original_formula_weight         1108.38
_cod_database_code               7246322
_chemical_oxdiff_formula         'C H N S Se'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V)
2.b Idealised Me refined as rotating group:
 C00W(H00A,H00B,H00C)
;
_shelx_res_checksum              18145
_shelx_shelxl_version_number     2014/7
_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 4.724
_oxdiff_exptl_absorpt_empirical_full_min 0.763