Phosphine-catalyzed [3 + 2] annulation of 2-aminoacrylates with allenoates and mechanistic studies
Wu, Xiao-Yun; Gui, Hou-Ze; Jangra, Harish; Wei, Yin; Zipse, Hendrik; Shi, Min; Catalysis Science & Technology 10 (2020) 3959–3964; doi:10.1039/D0CY00092B

data_1558022
_publ_section_title
;
 Phosphine-catalyzed [3 + 2] annulation of 2-aminoacrylates with
 allenoates and mechanistic studies
;
_journal_issue                   12
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              3959
_journal_page_last               3964
_journal_paper_doi               10.1039/D0CY00092B
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C15 H19 N O6 S'
_chemical_formula_sum            'C15 H19 N O6 S'
_chemical_formula_weight         341.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-04 deposited with the CCDC.	2020-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3705(2)
_cell_length_b                   7.27390(10)
_cell_length_c                   31.8622(5)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.93
_cell_measurement_theta_min      5.63
_cell_volume                     3098.78(8)
_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      170.02
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            30140
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.938
_diffrn_reflns_theta_min         5.625
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.393
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0941 before and 0.0493 after correction. The Ratio of minimum to maximum transmission is 0.7898. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+1.7663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2733
_reflns_number_total             2913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cy00092b3.cif
_cod_data_source_block           mj19431
_cod_depositor_comments
;Adding full bibliography for 1558022.cif.

 Adding full bibliography for 1558022.cif.
;
_cod_database_code               1558022
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.851
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              83704
_olex2_submission_special_instructions 'No special instructions were received'