AlCl3-Catalyzed Intramolecular Cyclization of N-Arylpropynamides with N-Sulfanylsuccinimides: Divergent Synthesis of 3-Sulfenyl Quinolin-2-ones and Azaspiro[4,5]trienones.
Gao, Wen-Chao; Liu, Tao; Cheng, Yu-Fei; Chang, Hong-Hong; Li, Xing; Zhou, Rong; Wei, Wen-Long; Qiao, Yan; The Journal of organic chemistry 82 (2017) 13459–13467; doi:10.1021/acs.joc.7b02498

data_4033188
_publ_section_title
;
 AlCl3-Catalyzed Intramolecular Cyclization of N-Arylpropynamides with
 N-Sulfanylsuccinimides: Divergent Synthesis of 3-Sulfenyl Quinolin-2-ones
 and Azaspiro[4,5]trienones.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13459
_journal_page_last               13467
_journal_paper_doi               10.1021/acs.joc.7b02498
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C25 H21 N O S'
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_space_group_name_H-M_alt        'P n a 21'
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_symmetry_space_group_name_H-M   'P n a 21'
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_cell_angle_beta                 90
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_cell_length_b                   14.8888(6)
_cell_length_c                   9.6210(4)
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_computing_cell_refinement       'Bruker SAINT'
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_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
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_diffrn_reflns_limit_k_min       -19
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_diffrn_reflns_limit_l_min       -11
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_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
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_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6951
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_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1161 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
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_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0414P)^2^+0.1822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.861
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                3389
_reflns_number_total             4395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02498_si_002.cif
_cod_data_source_block           170424A
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033188.cif.
;
_cod_database_code               4033188
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              41703
_shelx_hkl_checksum              98675