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_7220090
_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         'C26 H22 N2 O3, C2 H6 O S'
_chemical_formula_sum            'C28 H28 N2 O4 S'
_chemical_formula_weight         488.58
_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
_audit_creation_date             2014-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-02-14 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                97.33(3)
_cell_angle_beta                 104.20(3)
_cell_angle_gamma                110.31(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4629(19)
_cell_length_b                   10.003(2)
_cell_length_c                   14.426(3)
_cell_measurement_reflns_used    3987
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      1.4977
_cell_volume                     1207.0(6)
_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., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution
;
 'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0886
_diffrn_orient_matrix_UB_12      -0.0461
_diffrn_orient_matrix_UB_13      0.0638
_diffrn_orient_matrix_UB_21      -0.0390
_diffrn_orient_matrix_UB_22      0.0689
_diffrn_orient_matrix_UB_23      0.0758
_diffrn_orient_matrix_UB_31      -0.0635
_diffrn_orient_matrix_UB_32      0.0232
_diffrn_orient_matrix_UB_33      -0.0289
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15687
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         1.498
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8984
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0333P)^2^+0.6801P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4878
_reflns_number_total             5523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra04374c2.cif
_cod_data_source_block           sa3361
_cod_original_cell_volume        1207.1(5)
_cod_database_code               7220090
_shelxl_version_number           2013-4
_diffrn_number_total             5523
_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:
 C9(H9), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              47069
_shelx_hkl_checksum              43093