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_7124394
_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_formula_moiety         'C24 H25 N3 O4'
_chemical_formula_sum            'C24 H25 N3 O4'
_chemical_formula_weight         419.47
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc232nlg
_audit_creation_date             2018-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2019-07-08 deposited with the CCDC.    2019-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.841(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8382(9)
_cell_length_b                   15.3232(10)
_cell_length_c                   11.6575(9)
_cell_measurement_reflns_used    7786
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.4540
_cell_measurement_theta_min      2.1920
_cell_volume                     2089.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 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      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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   -115.00  65.00   1.00    8.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    8.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    8.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0558716000
_diffrn_orient_matrix_UB_12      -0.0173294000
_diffrn_orient_matrix_UB_13      -0.0031408000
_diffrn_orient_matrix_UB_21      -0.0225321000
_diffrn_orient_matrix_UB_22      0.0429654000
_diffrn_orient_matrix_UB_23      -0.0008236000
_diffrn_orient_matrix_UB_31      -0.0061189000
_diffrn_orient_matrix_UB_32      0.0002634000
_diffrn_orient_matrix_UB_33      -0.0615204000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21642
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.741
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.082(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0760P)^2^+0.4550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3174
_reflns_number_total             4254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07346a2.cif
_cod_data_source_block           r20180613a
_cod_database_code               7124394
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 92.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.91
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.710
_oxdiff_exptl_absorpt_empirical_full_min 0.614