Brønsted Acid Catalyzed Annulations of Ketene Dithioacetals: Synthesis of 3-Aryl Coumarins and Indenes
Arora, Shivani; Singh, Surya Pratap; Sharma, Parashuram; Singh, Anand; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01558G

data_7158952
_publ_section_title
;
 Br\/onsted Acid Catalyzed Annulations of Ketene Dithioacetals: Synthesis
 of 3-Aryl Coumarins and Indenes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01558G
_journal_year                    2022
_chemical_formula_moiety         'C20 H20 O3 S2'
_chemical_formula_sum            'C20 H20 O3 S2'
_chemical_formula_weight         372.48
_chemical_name_systematic
'5,6,7-trimethoxy-2-phenylspiro [indene-1,2'- [1,3] dithiolane'
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-17
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2022-08-09 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8279(5)
_cell_length_b                   6.5765(3)
_cell_length_c                   25.3023(11)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.23
_cell_volume                     1766.09(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            26159
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         3.205
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1014 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.9106.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+1.5705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3915
_reflns_number_total             4372
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01558g2.cif
_cod_data_source_block           6janb_0m
_cod_database_code               7158952
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.933
_olex2_refinement_description
;
1. 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
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C11(H11), C12(H12), C15(H15), C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              5506
_olex2_submission_special_instructions 'No special instructions were received'