Synthesis of 3-Sulfenylated Coumarins: BF<sub>3</sub>·Et<sub>2</sub>O-Mediated Electrophilic Cyclization of Aryl Alkynoates Using N-Sulfanylsuccinimides.
Gao, Wen-Chao; Liu, Tao; Zhang, Bing; Li, Xing; Wei, Wen-Long; Liu, Qiang; Tian, Jun; Chang, Hong-Hong; The Journal of organic chemistry 81 (2016) 11297–11304; doi:10.1021/acs.joc.6b02271

data_4037417
_publ_section_title
;
 Synthesis of 3-Sulfenylated Coumarins:
 BF<sub>3</sub>&#x00B7;Et<sub>2</sub>O-Mediated Electrophilic Cyclization
 of Aryl Alkynoates Using N-Sulfanylsuccinimides.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11297
_journal_page_last               11304
_journal_paper_doi               10.1021/acs.joc.6b02271
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C23 H18 O2 S'
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_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4070(8)
_cell_length_b                   13.2405(11)
_cell_length_c                   15.2351(14)
_cell_measurement_reflns_used    8093
_cell_measurement_temperature    258(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.97
_cell_volume                     1897.6(3)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      258(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0333
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.995
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_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_limit_k_max       15
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_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.042
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_min         2.974
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6248
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0459P)^2^+0.1880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2905
_reflns_number_total             3348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02271_si_002.cif
_cod_data_source_block           160704c
_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/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/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_database_code               4037417
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              85894
_shelx_hkl_checksum              92747