Phosphine-catalyzed [4 + 3] Cycloaddition Reaction of Aromatic Azomethine Imines with Allenoates
Guo, Hongchao; Li, Zhen; Yu, Hao; Feng, Yalin; Hou, Zhanfeng; Zhang, Lei; Yang, Wenjun; Wu, Yang; Xiao, Yumei; RSC Adv.  (2015) –; doi:10.1039/C5RA04374C

data_7220087
_publ_section_title
;
 Phosphine-catalyzed [4 + 3] Cycloaddition Reaction of Aromatic Azomethine
 Imines with Allenoates
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA04374C
_journal_year                    2015
_chemical_formula_moiety         'C28 H26 N2 O3'
_chemical_formula_sum            'C28 H26 N2 O3'
_chemical_formula_weight         438.51
_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
_audit_creation_date             2014-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2015-02-14 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.211(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5503(19)
_cell_length_b                   17.424(4)
_cell_length_c                   15.187(3)
_cell_measurement_reflns_used    6359
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4851
_cell_measurement_theta_min      1.1687
_cell_volume                     2244.7(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0275
_diffrn_orient_matrix_UB_12      0.0802
_diffrn_orient_matrix_UB_13      -0.0819
_diffrn_orient_matrix_UB_21      -0.0469
_diffrn_orient_matrix_UB_22      0.0301
_diffrn_orient_matrix_UB_23      0.0137
_diffrn_orient_matrix_UB_31      0.0367
_diffrn_orient_matrix_UB_32      0.0394
_diffrn_orient_matrix_UB_33      0.0389
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14344
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.787
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5103
_refine_ls_number_restraints     116
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0374P)^2^+1.0903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4768
_reflns_number_total             5103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra04374c2.cif
_cod_data_source_block           sa3591
_cod_original_cell_volume        2244.6(9)
_cod_database_code               7220087
_shelxl_version_number           2013-4
_diffrn_number_total             5282
_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. Restrained distances
 O3A-C20 = O3-C20
 1.34 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O2 \\sim O3 \\sim C21 \\sim C22 \\sim O3A \\sim C21A \\sim C22A \\sim O2A:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(C22A) \\sim Ueq,
Uanis(O2A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(O3A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(O2A)=1-FVAR(1)
 Sof(O2)=Sof(O3)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B), C21A(H21C,H21D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F)
;
_shelx_res_checksum              80927
_shelx_hkl_checksum              78095