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_7125357
_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         'C12 H11 Cl2 N O2 S'
_chemical_formula_sum            'C12 H11 Cl2 N O2 S'
_chemical_formula_weight         304.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-14 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.80(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.687(2)
_cell_length_b                   9.6570(19)
_cell_length_c                   11.950(2)
_cell_measurement_reflns_used    3701
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      2.72
_cell_volume                     1339.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT A '
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9983
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11542
_diffrn_reflns_theta_full        24.9949
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.8839
_exptl_absorpt_correction_T_min  0.8329
_exptl_absorpt_correction_type   none
_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    1.5087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             625.9112
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.3371
_refine_diff_density_min         -0.8766
_refine_diff_density_rms         0.1275
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             7.4901
_refine_ls_goodness_of_fit_ref   1.0563
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.0547
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0954
_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^)+(0.1651P)^2^+4.5730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2761
_refine_ls_wR_factor_ref         0.2893
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1967
_reflns_number_total             2347
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8cc09595g2.cif
_cod_data_source_block           T
_cod_original_cell_volume        1339.2(5)
_cod_database_code               7125357
_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. Rigid bond restraints
 C5, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C5 \\sim C6: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Others
 Fixed Sof: H1(0) H4(0)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3)
5.d X=CH2 refined with riding coordinates:
 N1(H1a,H1b)
5.e Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c)
;
_olex2_submission_special_instructions 'No special instructions were received'