Synthesis of organoselenyl isoquinolinium imides <i>via</i> iron(III) chloride-mediated tandem cyclization/selenation of <i>N</i>'-(2-alkynylbenzylidene)hydrazides and diselenides.
Yao, Hai-Feng; Wang, Dian-Liang; Li, Fang-Hui; Wu, Bing; Cai, Zhong-Jian; Ji, Shun-Jun; Organic & biomolecular chemistry 18 (2020) 7577–7584; doi:10.1039/d0ob01517b

data_7157706
_publ_section_title
;
 Synthesis of organoselenyl isoquinolinium imides <i>via</i> iron(III)
 chloride-mediated tandem cyclization/selenation of
 <i>N</i>'-(2-alkynylbenzylidene)hydrazides and diselenides.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7577
_journal_page_last               7584
_journal_paper_doi               10.1039/d0ob01517b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C28 H21 F N2 O2 S Se'
_chemical_formula_sum            'C28 H21 F N2 O2 S Se'
_chemical_formula_weight         547.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-09 deposited with the CCDC.	2020-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.15(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.215(3)
_cell_length_b                   11.927(2)
_cell_length_c                   15.344(3)
_cell_measurement_reflns_used    11441
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.9080
_cell_measurement_theta_min      2.1785
_cell_volume                     2372.8(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12186
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.864
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.708
_exptl_absorpt_correction_T_max  34.9080
_exptl_absorpt_correction_T_min  2.1785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.7065
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0413P)^2^+3.2857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4535
_reflns_number_total             4819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01517b2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 7157706.cif.'
_cod_original_cell_volume        2372.9(9)
_cod_database_code               7157706
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.548
_shelx_estimated_absorpt_t_min   0.427
_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. Others
 Sof(H17)=Sof(F1A)=1-FVAR(1)
 Sof(H21)=Sof(F1)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C26(H26), C27(H27)
3.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'