Modular synthesis of fluorinated 2<i>H</i>-thiophenes <i>via</i> [4 + 1] cyclization of enaminothiones.
Zhang, Xinyu; Zhang, Jinli; Chen, Jie; Zhou, Banghua; Zhang, Jian; Chen, Shunhong; Wu, Jian; Jiang, Yaojia; Organic & biomolecular chemistry 21 (2023) 3345–3349; doi:10.1039/d3ob00222e

data_7159258
_publ_section_title
;
 Modular synthesis of fluorinated 2<i>H</i>-thiophenes <i>via</i> [4 + 1]
 cyclization of enaminothiones.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3345
_journal_page_last               3349
_journal_paper_doi               10.1039/d3ob00222e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C19 H18 F3 N S'
_chemical_formula_weight         349.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2021-03-19 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8319(12)
_cell_length_b                   15.3118(13)
_cell_length_c                   6.5989(6)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    293.(2)
_cell_measurement_theta_max      30.2382
_cell_measurement_theta_min      3.5978
_cell_volume                     1700.7(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            22068
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.346
_refine_ls_abs_structure_details
;

Flack x determined using 1037 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0741
_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^)+(0.0403P)^2^+2.6850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1722
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.878
_reflns_Friedel_fraction_max     0.836
_reflns_number_gt                3038
_reflns_number_total             3748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00222e2.cif
_cod_data_source_block           ZJL2
_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 7159258.cif.
;
_cod_database_code               7159258
_shelx_res_checksum              4574
_shelx_hkl_checksum              16432