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_7125360
_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_formula_moiety         'C3 H6 N2 O2 S'
_chemical_formula_sum            'C3 H6 N2 O2 S'
_chemical_formula_weight         134.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2018-01-31
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_audit_update_record
;
2018-06-28 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.933(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.3625(4)
_cell_length_b                   9.5369(4)
_cell_length_c                   16.9216(7)
_cell_measurement_reflns_used    2805
_cell_measurement_temperature    293.67(10)
_cell_measurement_theta_max      28.4420
_cell_measurement_theta_min      3.7860
_cell_volume                     1183.76(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.67(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_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    -20.00  55.00   1.00    2.11    --   16.13 -99.00  30.00   75
  2  \w    -53.00  85.00   1.00    2.11    --   16.13   0.00-150.00  138
  3  \w    -85.00   0.00   1.00    2.11    --  -17.23 -57.00-150.00   85
  4  \w    -51.00 -24.00   1.00    2.11    --   16.13 -57.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0344123000
_diffrn_orient_matrix_UB_12      0.0635770000
_diffrn_orient_matrix_UB_13      0.0170970000
_diffrn_orient_matrix_UB_21      0.0102157000
_diffrn_orient_matrix_UB_22      -0.0326383000
_diffrn_orient_matrix_UB_23      0.0377943000
_diffrn_orient_matrix_UB_31      0.0898098000
_diffrn_orient_matrix_UB_32      -0.0206090000
_diffrn_orient_matrix_UB_33      -0.0069614000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8001
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.50
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.456
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
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    1.5054
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             561.2491
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2191
_refine_diff_density_min         -0.2523
_refine_diff_density_rms         0.0687
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.8143
_refine_ls_goodness_of_fit_ref   1.0733
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0733
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.5396P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -6
_reflns_number_gt                1728
_reflns_number_total             2081
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8cc09595g2.cif
_cod_data_source_block           zgf-20180104
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7125360
_chemical_oxdiff_formula         'C1 H1 O1 S1'
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N11(H11)
2.b X=CH2 refined with riding coordinates:
 N15(H15a,H15b), N7(H7a,H7b)
2.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C6(H6a,H6b,H6c)
;
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.563