Fast Oxy-Cope Rearrangements of Bis-alkynes: Competition with Central C-C Bond Fragmentation and Incorporation in Tunable Cascades Diverging from a Common Bis-allenic Intermediate
Runa Pal; Ronald J. Clark; Mariappan Manoharan; Igor V. Alabugin; Journal of Organic Chemistry 75 (2010) 8689–8692; doi:10.1021/jo101838a

data_4025886
_publ_section_title
;
 Fast Oxy-Cope Rearrangements of Bis-alkynes: Competition with Central C-C
 Bond Fragmentation and Incorporation in Tunable Cascades Diverging from a
 Common Bis-allenic Intermediate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8689
_journal_page_last               8692
_journal_paper_doi               10.1021/jo101838a
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C30 H22 O2'
_chemical_formula_sum            'C30 H22 O2'
_chemical_formula_weight         414.48
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.825(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.8890(2)
_cell_length_b                   12.0381(4)
_cell_length_c                   14.7561(5)
_cell_measurement_reflns_used    4891
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.79
_cell_measurement_theta_min      2.19
_cell_volume                     1042.39(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11330
_diffrn_reflns_theta_full        21.81
_diffrn_reflns_theta_max         21.81
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_coef       0.0123(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         1249
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      2.136
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0455
_refine_ls_wR_factor_ref         0.0459
_reflns_number_gt                1181
_reflns_number_total             1249
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101838a_si_005.cif
_cod_data_source_block           igor85
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_Hall     P-2yc
_cod_database_code               4025886