Stereoselective, Cascade Synthesis of trans-Enynones through Coupling-Isomerization Reaction.
Chinta, Bhavani Shankar; Baire, Beeraiah; The Journal of organic chemistry 80 (2015) 10208–10217; doi:10.1021/acs.joc.5b01780

data_4036395
_publ_section_title
;
 Stereoselective, Cascade Synthesis of trans-Enynones through
 Coupling-Isomerization Reaction.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10208
_journal_page_last               10217
_journal_paper_doi               10.1021/acs.joc.5b01780
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C17 H13 N O '
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5809(3)
_cell_length_b                   14.4420(7)
_cell_length_c                   16.1693(7)
_cell_measurement_reflns_used    2903
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.82
_cell_volume                     1303.24(11)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5351
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.891
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
; 
 Flack x determined using 748 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.0613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2016
_reflns_number_total             2294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01780_si_003.cif
_cod_data_source_block           769
_cod_database_code               4036395
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              81416
_shelx_hkl_checksum              52344