Iron(iii) chloride-promoted cyclization of α,β-alkynic tosylhydrazones with diselenides: synthesis of 4-(arylselanyl)-1H-pyrazoles.
Yao, Hai-Feng; Li, Fang-Hui; Li, Jian; Wang, Shun-Yi; Ji, Shun-Jun; Organic & biomolecular chemistry 18 (2020) 1987–1993; doi:10.1039/d0ob00048e

data_7157356
_publ_section_title
;
 Iron(iii) chloride-promoted cyclization of \a,\b-alkynic tosylhydrazones
 with diselenides: synthesis of 4-(arylselanyl)-1H-pyrazoles.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1987
_journal_page_last               1993
_journal_paper_doi               10.1039/d0ob00048e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C21 H16 N2 Se'
_chemical_formula_sum            'C21 H16 N2 Se'
_chemical_formula_weight         375.32
_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   mixed
_atom_sites_solution_primary     direct
_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.	2020-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.91(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.244(2)
_cell_length_b                   9.6663(19)
_cell_length_c                   16.765(3)
_cell_measurement_reflns_used    5461
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.7606
_cell_measurement_theta_min      2.2796
_cell_volume                     1658.0(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (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  0.0261
_diffrn_reflns_av_unetI/netI     0.0288
_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       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8260
_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         26.368
_diffrn_reflns_theta_min         2.280
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.268
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.8464
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0408P)^2^+0.9680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3191
_reflns_number_total             3360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00048e2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157356.cif.
;
_cod_original_cell_volume        1658.1(6)
_cod_database_code               7157356
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.343
_shelx_estimated_absorpt_t_min   0.300
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'