(3+2) Cycloadditions of Thiouronium Ylides: A Room-Temperature, One-Pot Approach to Dihydrothiophenes.
Neuhaus, James D.; Angyal, Peter; Oost, Rik; Maulide, Nuno; The Journal of organic chemistry 83 (2018) 2479–2485; doi:10.1021/acs.joc.7b03255

data_4033497
_publ_section_title
;
 (3+2) Cycloadditions of Thiouronium Ylides: A Room-Temperature, One-Pot
 Approach to Dihydrothiophenes.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2479
_journal_page_last               2485
_journal_paper_doi               10.1021/acs.joc.7b03255
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C19 H18 N2 O3 S, 0.13(H2 O)'
_chemical_formula_sum            'C19 H18.25 N2 O3.12 S'
_chemical_formula_weight         356.66
_chemical_name_systematic
;
+- ((2R,3R)-5-(dimethylamino)-4-nitro-3-phenyl-2,3-dihydrothiophen-2-yl)
(phenyl)methanone
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
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;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                78.820(4)
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_cell_length_a                   10.2656(10)
_cell_length_b                   10.2864(10)
_cell_length_c                   18.0426(18)
_cell_measurement_reflns_used    9233
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.065
_cell_measurement_theta_min      2.322
_cell_volume                     1706.2(3)
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_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator
;
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
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_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            94905
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.271
_diffrn_reflns_theta_min         2.450
_diffrn_source                   'sealed X-ray tube'
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.1071 before and 0.0413 after correction. 
The Ratio of minimum to maximum transmission is 0.9354. 
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             749
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         10065
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0376P)^2^+0.8269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9168
_reflns_number_total             10065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03255_si_002.cif
_cod_data_source_block           jane435_p-1
_cod_depositor_comments          'Adding full bibliography for 4033497.cif.'
_cod_database_code               4033497
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.955