Phosphine-Catalyzed (3+2)/(2+3) Sequential Annulation by Triple Nucleophilic Addition Reaction of γ-Vinyl Allenoates
Huang, You; Feng, Jiaxu; Chemical Communications  (2019) –; doi:10.1039/C9CC07346A

data_7124393
_publ_section_title
;
 Phosphine-Catalyzed (3+2)/(2+3) Sequential Annulation by Triple
 Nucleophilic Addition Reaction of \g-Vinyl Allenoates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07346A
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H25 N3 O4, C H Cl3'
_chemical_formula_sum            'C25 H26 Cl3 N3 O4'
_chemical_formula_weight         538.84
_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_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc232nnj
_audit_creation_date             2018-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-08 deposited with the CCDC.    2019-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.54(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.740(2)
_cell_length_b                   22.857(5)
_cell_length_c                   10.909(2)
_cell_measurement_reflns_used    4831
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      27.8784
_cell_measurement_theta_min      1.9286
_cell_volume                     2592.2(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31346
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.819
_diffrn_reflns_theta_min         1.959
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear(Rigaku, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 2112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.49(5)
_refine_ls_extinction_coef       0.0057(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     642
_refine_ls_number_reflns         11931
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0713
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0752P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                8205
_reflns_number_total             11931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07346a2.cif
_cod_data_source_block           r20181026b1
_cod_database_code               7124393
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.926
_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. Restrained distances
 N3-H3 = N6-H6A
 0.9 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C20(H20), C44(H44), C49(H49), C50(H50)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C19(H19A,H19B), C35(H35A,H35B), C42(H42A,
 H42B), C43(H43A,H43B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C37(H37),
  C38(H38), C39(H39), C40(H40), C41(H41), C45(H45), C46(H46)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              61517
_olex2_submission_special_instructions 'No special instructions were received'