Phosphine-Triggered Selectivity Switch in Silver-Catalyzed o-Alkynylbenzohydroxamic Acid Cycloisomerizations.
Bantreil, Xavier; Bourderioux, Aurélie; Mateo, Pierre; Hagerman, Caroline E.; Selkti, Mohamed; Brachet, Etienne; Belmont, Philippe; Organic letters 18 (2016) 4814–4817; doi:10.1021/acs.orglett.6b02235

data_1555726
_publ_section_title
;
 Phosphine-Triggered Selectivity Switch in Silver-Catalyzed
 o-Alkynylbenzohydroxamic Acid Cycloisomerizations.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4814
_journal_page_last               4817
_journal_paper_doi               10.1021/acs.orglett.6b02235
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C16 H19 N O4'
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7082(12)
_cell_length_b                   10.0795(9)
_cell_length_c                   24.4296(18)
_cell_measurement_reflns_used    3272
_cell_measurement_temperature    292.2(6)
_cell_measurement_theta_max      27.7960
_cell_measurement_theta_min      3.8920
_cell_volume                     3129.2(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.2(6)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0282187000
_diffrn_orient_matrix_UB_12      0.0522409000
_diffrn_orient_matrix_UB_13      0.0127465000
_diffrn_orient_matrix_UB_21      -0.0161584000
_diffrn_orient_matrix_UB_22      -0.0235498000
_diffrn_orient_matrix_UB_23      0.0260474000
_diffrn_orient_matrix_UB_31      0.0453735000
_diffrn_orient_matrix_UB_32      -0.0408475000
_diffrn_orient_matrix_UB_33      0.0013268000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_sigmaI/netI    0.1254
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23820
_diffrn_reflns_theta_full        29.89
_diffrn_reflns_theta_max         29.8883
_diffrn_reflns_theta_min         3.5939
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0592
_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^)+(0.0928P)^2^+0.3830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1879
_reflns_number_gt                2603
_reflns_number_total             4051
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02235_si_002.cif
_cod_data_source_block           eb794-1
_cod_database_code               1555726
_oxdiff_exptl_absorpt_empirical_full_min 0.388
_oxdiff_exptl_absorpt_empirical_full_max 7.133
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;