Base-mediated cascade synthesis of indole diolefins: a route to spiro[cyclopentene-indole]thiones and thiepino[2,3-<i>b</i>]indoles.
Muthusamy, Sengodagounder; Naveen, Ramasamy; Kumar, Muniyappankovilthottam Devaraj Senthil; Chemical communications (Cambridge, England) 59 (2023) 8560–8563; doi:10.1039/d3cc01870a

data_7131855
_publ_section_title
;
 Base-mediated cascade synthesis of indole diolefins: a route to
 spiro[cyclopentene-indole]thiones and thiepino[2,3-<i>b</i>]indoles.
;
_journal_issue                   55
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8560
_journal_page_last               8563
_journal_paper_doi               10.1039/d3cc01870a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C19 H16 Br N S'
_chemical_formula_weight         370.29
_chemical_name_common            ORGANIC
_chemical_name_systematic        spiro-indolocyclopentene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2023-04-04 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                88.563(6)
_cell_angle_beta                 78.673(6)
_cell_angle_gamma                72.965(6)
_cell_formula_units_Z            4
_cell_length_a                   9.382(2)
_cell_length_b                   10.472(2)
_cell_length_c                   17.945(4)
_cell_measurement_reflns_used    7433
_cell_measurement_temperature    303.(2)
_cell_measurement_theta_max      30.4025
_cell_measurement_theta_min      2.3066
_cell_volume                     1651.9(6)
_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      303.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1559
_diffrn_reflns_av_unetI/netI     0.1416
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            65104
_diffrn_reflns_theta_full        32.54
_diffrn_reflns_theta_max         32.54
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'MICRO FOCUS TUBE'
_exptl_absorpt_coefficient_mu    2.610
_exptl_absorpt_correction_T_max  0.8090
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and hexane'
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.592
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         11747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.2098
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0958P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.2212
_reflns_number_gt                4124
_reflns_number_total             11747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01870a2.cif
_cod_data_source_block           SMR151
_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 8170 2020-07-09 18:12:32Z antanas 

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H32 Br2 N2 S2'
_cod_original_formula_weight         740.59
_cod_original_formula_units_Z            2
_cod_database_code               7131855
_shelx_res_checksum              28493
_shelx_hkl_checksum              94686