Thiourea participation in [3+2] cycloaddition with donor-acceptor cyclopropanes: a domino process to 2-amino-dihydrothiophenes.
Xie, Ming-Sheng; Zhao, Guo-Feng; Qin, Tao; Suo, Yong-Bo; Qu, Gui-Rong; Guo, Hai-Ming; Chemical communications (Cambridge, England) 55 (2019) 1580–1583; doi:10.1039/c8cc09595g

data_7125359
_publ_section_title
;
 Thiourea participation in [3+2] cycloaddition with donor-acceptor
 cyclopropanes: a domino process to 2-amino-dihydrothiophenes.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1580
_journal_page_last               1583
_journal_paper_doi               10.1039/c8cc09595g
_journal_volume                  55
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H13 N O2 S'
_chemical_formula_sum            'C12 H13 N O2 S'
_chemical_formula_weight         235.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-28 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.003(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5830(2)
_cell_length_b                   6.1506(1)
_cell_length_c                   25.4866(5)
_cell_measurement_reflns_used    8800
_cell_measurement_temperature    294
_cell_measurement_theta_max      71.8760
_cell_measurement_theta_min      5.8340
_cell_volume                     1184.17(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9753
_diffrn_measured_fraction_theta_max 0.9753
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -53.00  31.00   1.00    1.50    --  -36.07  57.00 -90.00   84
  2  \w    -69.00  33.00   1.00    1.50    --  -36.07  89.00  13.00  102
  3  \w    -12.00  69.00   1.00    1.50    --   36.07 -89.00-101.00   81
  4  \w      1.00  75.00   1.00    1.50    --   36.07 -99.00-120.00   74
  5  \w    -33.00  55.00   1.00    1.50    --   36.07 -38.00  30.00   88
  6  \w     17.00 105.00   1.00    1.50    --   36.07  38.00 150.00   88
  7  \w    -31.00  63.00   1.00    1.50    --   36.07 -77.00 -90.00   94
  8  \w    -33.00  55.00   1.00    1.50    --   36.07 -38.00 -30.00   88
  9  \w    -33.00  55.00   1.00    1.50    --   36.07 -38.00 -90.00   88
 10  \w     19.00 103.00   1.00    1.50    --   36.07  57.00-180.00   84
 11  \w      1.00  75.00   1.00    1.50    --   36.07 -99.00   0.00   74
 12  \w     23.00  89.00   1.00    1.50    --   36.07-125.00 -90.00   66
 13  \w      1.00  75.00   1.00    1.50    --   36.07 -99.00 120.00   74
 14  \w    -33.00  55.00   1.00    1.50    --   36.07 -38.00 120.00   88
 15  \w     39.00 131.00   1.00    4.50    --  109.31 -30.00 -60.00   92
 16  \w     42.00 127.00   1.00    4.50    --  109.31 -61.00  30.00   85
 17  \w     92.00 178.00   1.00    4.50    --  109.31  45.00  60.00   86
 18  \w     40.00 109.00   1.00    4.50    --  109.31 -95.00-150.00   69
 19  \w     57.00 151.00   1.00    4.50    --  109.31 178.00 -90.00   94
 20  \w     39.00 116.00   1.00    4.50    --  109.31-111.00 -60.00   77
 21  \w     71.00 178.00   1.00    4.50    --  109.31  15.00-180.00  107
 22  \w     71.00 178.00   1.00    4.50    --  109.31  15.00 120.00  107
 23  \w     39.00 131.00   1.00    4.50    --  109.31 -30.00  90.00   92
 24  \w     57.00 151.00   1.00    4.50    --  109.31 178.00 150.00   94
 25  \w     40.00 109.00   1.00    4.50    --  109.31 -95.00   0.00   69
 26  \w     57.00 151.00   1.00    4.50    --  109.31 178.00-180.00   94
 27  \w    100.00 178.00   1.00    4.50    --  109.31  89.00  13.00   78
 28  \w     41.00 127.00   1.00    4.50    --  109.31 -45.00-120.00   86
 29  \w      9.00 104.00   1.00    1.50    --   36.07  77.00-150.00   95
 30  \w     17.00 105.00   1.00    1.50    --   36.07  38.00  90.00   88
 31  \w      9.00 104.00   1.00    1.50    --   36.07  77.00 -30.00   95
 32  \w     19.00 103.00   1.00    1.50    --   36.07  57.00 120.00   84
 33  \w      9.00 104.00   1.00    1.50    --   36.07  77.00 120.00   95
 34  \w      9.00 104.00   1.00    1.50    --   36.07  77.00  60.00   95
 35  \w      9.00 104.00   1.00    1.50    --   36.07  77.00 -90.00   95
 36  \w    -31.00  53.00   1.00    1.50    --   36.07 -57.00 120.00   84
 37  \w      1.00  75.00   1.00    1.50    --   36.07 -99.00  90.00   74
 38  \w     19.00 103.00   1.00    1.50    --   36.07  57.00  30.00   84
 39  \w     17.00 105.00   1.00    1.50    --   36.07  38.00 -30.00   88
 40  \w      9.00 104.00   1.00    1.50    --   36.07  77.00 150.00   95
 41  \w     19.00 103.00   1.00    1.50    --   36.07  57.00 -30.00   84
 42  \w     19.00 103.00   1.00    1.50    --   36.07  57.00 -90.00   84
 43  \w     88.00 178.00   1.00    4.50    --  109.31  30.00 -60.00   90
 44  \w     83.00 156.00   1.00    4.50    --  109.31  77.00  90.00   73
 45  \w     83.00 177.00   1.00    4.50    --  109.31  77.00-120.00   94
 46  \w     83.00 177.00   1.00    4.50    --  109.31  77.00 -60.00   94
 47  \w     88.00 178.00   1.00    4.50    --  109.31  30.00  30.00   90
 48  \w     88.00 178.00   1.00    4.50    --  109.31  30.00-150.00   90
 49  \w     92.00 178.00   1.00    4.50    --  109.31  45.00-120.00   86
 50  \w     88.00 178.00   1.00    4.50    --  109.31  30.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0698555000
_diffrn_orient_matrix_UB_12      -0.1655654000
_diffrn_orient_matrix_UB_13      0.0385648000
_diffrn_orient_matrix_UB_21      0.0471033000
_diffrn_orient_matrix_UB_22      0.1576343000
_diffrn_orient_matrix_UB_23      0.0460511000
_diffrn_orient_matrix_UB_31      -0.1856888000
_diffrn_orient_matrix_UB_32      0.1023721000
_diffrn_orient_matrix_UB_33      -0.0086331000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22056
_diffrn_reflns_theta_full        73.0353
_diffrn_reflns_theta_max         73.04
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3198
_exptl_crystal_description       block
_exptl_crystal_F_000             498.7537
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.2328
_refine_diff_density_min         -0.2232
_refine_diff_density_rms         0.0498
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.007(18)
_refine_ls_d_res_high            0.8060
_refine_ls_d_res_low             12.6947
_refine_ls_goodness_of_fit_ref   1.0693
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4627
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0693
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.1736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.965
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              31
_reflns_limit_l_min              -31
_reflns_number_gt                4218
_reflns_number_total             4627
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8cc09595g2.cif
_cod_data_source_block           SYB-CHANWU-1
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7125359
_chemical_oxdiff_formula         'C1 H1 S1 N1'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C22(H22), C5(H5), C4(H4), C3(H3), C18(H18), C20(H20),
 C21(H21), C19(H19)
2.d X=CH2 refined with riding coordinates:
 N32(H32a,H32b), N16(H16a,H16b)
2.e Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C30(H30a,H30b,H30c)
;
_olex2_date_sample_data_collection 2017-04-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.769
_oxdiff_exptl_absorpt_empirical_full_min 0.672