Coupling and Decoupling Approach Enables Palladium-Catalyzed Aerobic Bimolecular Carbocyclizations of Enediynes to 2,6-Diacylnaphthalenes.
Ling, Fei; Wan, Yanjun; Wang, Dongxu; Ma, Cheng; The Journal of organic chemistry 81 (2016) 2770–2781; doi:10.1021/acs.joc.5b02870

data_4031969
_publ_section_title
;
 Coupling and Decoupling Approach Enables Palladium-Catalyzed Aerobic
 Bimolecular Carbocyclizations of Enediynes to 2,6-Diacylnaphthalenes.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2770
_journal_page_last               2781
_journal_paper_doi               10.1021/acs.joc.5b02870
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C41 H26 N4 O14, 2(C1.5 H3 O0.5)'
_chemical_formula_sum            'C44 H32 N4 O15'
_chemical_formula_weight         856.74
_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             2015-04-27
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.046(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3311(8)
_cell_length_b                   19.2315(11)
_cell_length_c                   10.6080(7)
_cell_measurement_reflns_used    2343
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1975
_cell_measurement_theta_min      2.8542
_cell_volume                     2310.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0452660000
_diffrn_orient_matrix_UB_12      -0.0157710000
_diffrn_orient_matrix_UB_13      0.0345889000
_diffrn_orient_matrix_UB_21      0.0225472000
_diffrn_orient_matrix_UB_22      0.0161262000
_diffrn_orient_matrix_UB_23      0.0559607000
_diffrn_orient_matrix_UB_31      -0.0369346000
_diffrn_orient_matrix_UB_32      0.0291857000
_diffrn_orient_matrix_UB_33      -0.0122388000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9190
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.86
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1572P)^2^+0.6684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2350
_refine_ls_wR_factor_ref         0.2661
_reflns_number_gt                2907
_reflns_number_total             4227
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02870_si_002.cif
_cod_data_source_block           150427_lf20150427
_cod_original_cell_volume        2310.1(3)
_cod_database_code               4031969
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_reflns_odcompleteness_completeness 99.57
_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. Rigid bond restraints
 C7, C8, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O4, O5, N1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O6, O7, N2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N2 \\sim O6 \\sim O7 \\sim N1 \\sim O5 \\sim O4: within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.02
C7 \\sim C9 \\sim C8: within 3.8A with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(O8A)=0.5*(1-FVAR(2))
 Sof(O8)=0.5*FVAR(2)
 Fixed Sof: C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5) C23(0.5) H23A(0.5) H23B(0.5)
 H23C(0.5) C24(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5) C9(0.5) H9A(0.5)
 H9B(0.5) H9C(0.5) C8(0.5) H8A(0.5) H8B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C15(H15), C14(H14), C12(H12), C11(H11), C18(H18), C19(H19), C21(H21),
 C22(H22)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C9(H9A,H9B,H9C)
;