Catalytic [2+2+2] Cycloaddition with Indium(III)-Activated Formaldimines: A Practical and Selective Access to Hexahydropyrimidines and 1,3-Diamines from Alkenes
Zhou, Hui; Chaminda Lakmal, Hetti Handi; Baine, Jonathan; Valle, Henry; Xu, Xue; Cui, Xin; Chem. Sci.  (2017) –; doi:10.1039/C7SC02576A

data_1546620
_publ_section_title
;
 Catalytic [2+2+2] Cycloaddition with Indium(III)-Activated Formaldimines:
 A Practical and Selective Access to Hexahydropyrimidines and 1,3-Diamines
 from Alkenes
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC02576A
_journal_year                    2017
_chemical_formula_moiety         'C25 H29 N2 O4 S2'
_chemical_formula_sum            'C25 H29 N2 O4 S2'
_chemical_formula_weight         485.62
_chemical_name_systematic        MSU0048
_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     dual
_audit_creation_date             2017-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-06-06 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                103.702(2)
_cell_angle_beta                 107.842(2)
_cell_angle_gamma                96.750(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5654(7)
_cell_length_b                   10.5731(8)
_cell_length_c                   13.0829(9)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.29
_cell_volume                     1197.54(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26388
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.111
_diffrn_reflns_theta_min         2.241
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9655
_exptl_absorpt_correction_T_min  0.9248
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0674 before and 0.0369 after correction. The Ratio of minimum to maximum transmission is 0.9578. The \l/2 correction factor is Not present.'
_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    1.347
_exptl_crystal_description       Block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.232
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0397P)^2^+1.0354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4191
_reflns_number_total             4741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc02576a2.cif
_cod_data_source_block           msu0048
_cod_original_cell_volume        1197.53(15)
_cod_database_code               1546620
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.924
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H21(0.5) H3AA(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5)
 C6AA(0.5) H6AA(0.5) H6AB(0.5) H6AC(0.5)
3.a Ternary CH refined with riding coordinates:
 N2(H2), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C17(H17), C16(H16), C13(H13), C7(H7), C9(H9), C14(H14),
 C20(H20), C24(H24), C22(H22), C21(H21), C23(H3AA)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C11(H11A,H11B,H11C), C25(H25A,H25B,H25C), C6AA(H6AA,H6AB,
 H6AC)
;
_olex2_date_sample_completion    2017-03-16
_olex2_date_sample_data_collection 2017-03-16
_olex2_date_sample_submission    2017-03-16
_olex2_submission_original_sample_id MSU0048
_olex2_submission_special_instructions 'No special instructions were received'