Mechanistic studies of 1,3-dipolar cycloadditions of bicyclic thioisomünchnones with alkenes. A computational rationale focused on donor-acceptor interactions.
García de la Concepción, Juan; Ávalos, Martín; Cintas, Pedro; Jiménez, José L; Light, Mark E.; Organic & biomolecular chemistry 16 (2018) 3438–3452; doi:10.1039/c8ob00683k

data_7156200
_publ_section_title
;
 Mechanistic studies of 1,3-dipolar cycloadditions of bicyclic
 thioisom\"unchnones with alkenes. A computational rationale focused on
 donor-acceptor interactions.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3438
_journal_page_last               3452
_journal_paper_doi               10.1039/c8ob00683k
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C14 H12 N2 O S2'
_chemical_formula_sum            'C14 H12 N2 O S2'
_chemical_formula_weight         288.38
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-03
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2018-03-19 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                88.811(3)
_cell_angle_beta                 76.205(4)
_cell_angle_gamma                88.281(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6439(3)
_cell_length_b                   10.3733(3)
_cell_length_c                   11.1733(4)
_cell_measurement_reflns_used    8494
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.1200
_cell_measurement_theta_min      2.7230
_cell_volume                     634.93(5)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details
;
  1 omega  -39.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000   72.0000  150.0000 106

  2 omega  -73.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000   30.0000 88

  3 omega  -73.00   16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000 -150.0000 89

  4 omega  -68.00   11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000    0.0000 -180.0000 79

  5 omega  -38.00   -9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000   54.0000    0.0000 29

  6 omega  -62.00  -52.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000   72.0000  120.0000 10

  7 omega -113.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000    0.0000 -150.0000 180

  8 omega  -60.00   16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000    0.0000 76

  9 omega  -69.00   16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0000  -72.0000 -180.0000 85
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0706167000
_diffrn_orient_matrix_UB_12      -0.0228365000
_diffrn_orient_matrix_UB_13      0.0411124000
_diffrn_orient_matrix_UB_21      -0.0611902000
_diffrn_orient_matrix_UB_22      -0.0593985000
_diffrn_orient_matrix_UB_23      0.0065626000
_diffrn_orient_matrix_UB_31      0.0895932000
_diffrn_orient_matrix_UB_32      -0.0251180000
_diffrn_orient_matrix_UB_33      -0.0504025000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12461
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.334
_diffrn_reflns_theta_min         2.698
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0532P)^2^+0.1930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3796
_reflns_number_total             4143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00683k2.cif
_cod_data_source_block           2015acc0008
_cod_depositor_comments
'Adding full bibliography for 7156195--7156203.cif.'
_cod_original_cell_volume        634.93(4)
_cod_database_code               7156200
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 91.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.26
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_shelx_res_checksum              34899
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_submission    2015-03-02
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id acrCNalto
_olex2_submission_special_instructions 'No special instructions were received'