Time-economical synthesis of selenofunctionalized heterocycles <i>via</i> I<sub>2</sub>O<sub>5</sub>-mediated selenylative heterocyclization.
Zhou, Chen-Fan; Zhang, Yun-Qian; Ling, Yong; Ming, Liang; Xi, Xia; Liu, Gong-Qing; Zhang, Yanan; Organic & biomolecular chemistry 20 (2022) 420–426; doi:10.1039/d1ob02196f

data_7158447
_publ_section_title
;
 Time-economical synthesis of selenofunctionalized heterocycles <i>via</i>
 I<sub>2</sub>O<sub>5</sub>-mediated selenylative heterocyclization.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              420
_journal_page_last               426
_journal_paper_doi               10.1039/d1ob02196f
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H17 N O2 S2 Se'
_chemical_formula_sum            'C15 H17 N O2 S2 Se'
_chemical_formula_weight         386.37
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2021-10-20 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0638(5)
_cell_length_b                   8.2150(7)
_cell_length_c                   24.112(2)
_cell_measurement_reflns_used    2285
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      24.7130
_cell_measurement_theta_min      2.6090
_cell_volume                     1597.3(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_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 0.999
_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    -23.00  47.00   1.00    8.00    --  -11.59   0.00  60.00   70
  2  \w   -100.00 -58.00   1.00    8.00    --  -11.59   0.00  60.00   42
  3  \w    -13.00  19.00   1.00    8.00    --  -11.59  19.00   0.00   32
  4  \w     39.00  99.00   1.00    8.00    --   11.74-178.00   0.00   60
;
_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      0.0017509000
_diffrn_orient_matrix_UB_12      -0.0853979000
_diffrn_orient_matrix_UB_13      -0.0042730000
_diffrn_orient_matrix_UB_21      -0.0272348000
_diffrn_orient_matrix_UB_22      0.0112488000
_diffrn_orient_matrix_UB_23      -0.0277145000
_diffrn_orient_matrix_UB_31      0.0836084000
_diffrn_orient_matrix_UB_32      0.0054530000
_diffrn_orient_matrix_UB_33      -0.0089316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7121
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.619
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60317
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0341P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2471
_reflns_number_total             2808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02196f2.cif
_cod_data_source_block           se2
_cod_depositor_comments
'Adding full bibliography for 7158446--7158447.cif.'
_cod_database_code               7158447
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.51(2)
 0.49(2)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(S2A) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.2
4. Others
 Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(S2A)=1-FVAR(1)
 Sof(S2)=Sof(H15A)=Sof(H15B)=Sof(H14)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C3(H3), C4(H4), C14(H14), C5(H5)
5.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              54007
_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 1.518
_oxdiff_exptl_absorpt_empirical_full_min 0.831