Reactivity of epoxy-ynamides with metal halides: nucleophile (Br/Cl/OH)-assisted tandem intramolecular 5-exo-dig or 6-endo-dig cyclisation and AgF2-promoted oxidation
Anitha, Mandala; Shankar, Mallepalli; Kumara Swamy, K. C.; Organic Chemistry Frontiers 6 (2019) 1133–; doi:10.1039/C9QO00027E

data_1554703
_publ_section_title
;
 Reactivity of epoxy-ynamides with metal halides: nucleophile
 (Br/Cl/OH)-assisted tandem intramolecular 5-exo-dig or 6-endo-dig
 cyclisation and AgF2-promoted oxidation
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1133
_journal_paper_doi               10.1039/C9QO00027E
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C17 H16 Br3 N O2 S'
_chemical_formula_weight         538.10
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-12-15 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2985(3)
_cell_length_b                   12.4303(6)
_cell_length_c                   19.4432(8)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.50
_cell_volume                     1966.59(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32477
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    6.269
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1048
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.826
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+3.5045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2936
_reflns_number_total             3431
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9qo00027e2.cif
_cod_data_source_block           compound31
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1554703