Palladium-Catalyzed Construction of Tetracyclic Scaffolds via the 1,7-Enyne Carbocyclization/Iodophenol Dearomatization Cascade.
Xia, Yu; Wang, Li-Jing; Wang, Jia; Chen, Si; Shen, Yi; Guo, Chun-Huan; Liang, Yong-Min; The Journal of organic chemistry 82 (2017) 12386–12394; doi:10.1021/acs.joc.7b02196

data_4033120
_publ_section_title
;
 Palladium-Catalyzed Construction of Tetracyclic Scaffolds via the
 1,7-Enyne Carbocyclization/Iodophenol Dearomatization Cascade.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12386
_journal_page_last               12394
_journal_paper_doi               10.1021/acs.joc.7b02196
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C25 H21 N O2'
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.43
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.790(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.2457(10)
_cell_length_b                   9.0807(4)
_cell_length_c                   18.6858(9)
_cell_measurement_reflns_used    2400
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5040
_cell_measurement_theta_min      3.4750
_cell_volume                     3916.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   13.00   56.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -30.0000 43

  2 omega  -10.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -180.0000 34

  3 omega   -8.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -120.0000 74

  4 omega   -2.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000   60.0000 83
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0028053000
_diffrn_orient_matrix_UB_12      0.0437563000
_diffrn_orient_matrix_UB_13      -0.0308530000
_diffrn_orient_matrix_UB_21      0.0251291000
_diffrn_orient_matrix_UB_22      -0.0401489000
_diffrn_orient_matrix_UB_23      -0.0061334000
_diffrn_orient_matrix_UB_31      -0.0174539000
_diffrn_orient_matrix_UB_32      -0.0507381000
_diffrn_orient_matrix_UB_33      -0.0217306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14929
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1552
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.2130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1689
_reflns_number_gt                4120
_reflns_number_total             7713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02196_si_002.cif
_cod_data_source_block           xy_1102
_cod_depositor_comments
;
      Adding full bibliography for 4033120.cif.

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C25 H21 N O2)'
_cod_original_formula_sum        'C50 H42 N2 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     734.86
_cod_database_code               4033120
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28),
  C29(H29), C38(H38), C39(H39), C41(H41), C42(H42), C44(H44), C45(H45),
 C46(H46), C47(H47), C48(H48)
2.c Idealised Me refined as rotating group:
 C3BA(H3BA,H3BB,H3BC), C13(H13A,H13B,H13C), C0BA(H0BA,H0BB,H0BC), C37(H37A,
 H37B,H37C)
;
_olex2_date_sample_data_collection 2016-11-02
_olex2_submission_special_instructions 'No special instructions were received'