Synthesis of Cyclic Azomethine Imines by Cycloaddition Reactions of N-Isocyanates and N-Isothiocyanates.
Bongers, Amanda; Ranasinghe, Indee; Lemire, Philippe; Perozzo, Alyssa; Vincent-Rocan, Jean-François; Beauchemin, André M; Organic letters 18 (2016) 3778–3781; doi:10.1021/acs.orglett.6b01788

data_1555653
_publ_section_title
;
 Synthesis of Cyclic Azomethine Imines by Cycloaddition Reactions of
 N-Isocyanates and N-Isothiocyanates.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3778
_journal_page_last               3781
_journal_paper_doi               10.1021/acs.orglett.6b01788
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C14 H13 N3 O S'
_chemical_formula_weight         271.33
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                76.690(3)
_cell_angle_beta                 87.767(3)
_cell_angle_gamma                85.418(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6316(4)
_cell_length_b                   8.8731(6)
_cell_length_c                   13.3605(7)
_cell_measurement_reflns_used    2496
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.71
_cell_measurement_theta_min      2.37
_cell_volume                     647.47(7)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.980
_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_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3809
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.746
_diffrn_reflns_theta_min         1.567
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.745111
_exptl_absorpt_correction_T_min  0.643563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0707P)^2^+0.1116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1723
_reflns_number_total             2138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01788_si_002.cif
_cod_data_source_block           ab024_5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'n/a' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1555653
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2013-4
_shelx_res_checksum              58070
_shelx_hkl_checksum              3950