Synthesis of 4-Sulfenyl Isoxazoles through AlCl<sub>3</sub>-Mediated Electrophilic Cyclization and Sulfenylation of 2-Alkyn-1-one O-Methyloximes.
Gao, Wen-Chao; Cheng, Yu-Fei; Chang, Hong-Hong; Li, Xing; Wei, Wen-Long; Yang, Peng; The Journal of organic chemistry 84 (2019) 4312–4317; doi:10.1021/acs.joc.9b00256

data_4034295
_publ_section_title
;
 Synthesis of 4-Sulfenyl Isoxazoles through AlCl<sub>3</sub>-Mediated
 Electrophilic Cyclization and Sulfenylation of 2-Alkyn-1-one
 O-Methyloximes.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4312
_journal_page_last               4317
_journal_paper_doi               10.1021/acs.joc.9b00256
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C22 H16 Cl N O S'
_chemical_formula_sum            'C22 H16 Cl N O S'
_chemical_formula_weight         377.87
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                88.317(2)
_cell_angle_beta                 81.705(2)
_cell_angle_gamma                85.227(2)
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_cell_length_a                   6.0840(3)
_cell_length_b                   7.6921(4)
_cell_length_c                   19.8288(10)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      33.29
_cell_measurement_theta_min      3.12
_cell_volume                     914.93(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.96
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0250
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18235
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         3.115
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0658 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.8984.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0440P)^2^+0.4006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2836
_reflns_number_total             3193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00256_si_002.cif
_cod_data_source_block           mo_190110d_0m
_cod_database_code               4034295
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details   SADABS
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00D,H00G)
;
_shelx_res_checksum              34325
_shelx_hkl_checksum              42655
_olex2_submission_special_instructions 'No special instructions were received'