Triplet Reactivity and Regio-/Stereoselectivity in the Macrocyclization of Diastereomeric Ketoprofen-Quencher Conjugates via Remote Hydrogen Abstractions
Sergio Abad; Francisco Boscá; Luis R. Domingo; Salvador Gil; Uwe Pischel; Miguel A. Miranda; Journal of the American Chemical Society 129 (2007) 7407–7420; doi:10.1021/ja0712827

data_4109510
_publ_contact_author_address
'Avda. De los Naranjos s/n. 46022. Valencia. Spain.'
_publ_contact_author_email       mmiranda@qim.upv.es
_publ_contact_author_fax         0034963877809
_publ_contact_author_name        'Prof. Dr. Miguel Angel Miranda Alonso'
_publ_contact_author_phone       0034963877805
_publ_section_title
;
 Triplet Reactivity and Regio-/Stereoselectivity in the Macrocyclization
 of Diastereomeric Ketoprofen-Quencher Conjugates via Remote Hydrogen
 Abstractions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7407
_journal_page_last               7420
_journal_paper_doi               10.1021/ja0712827
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration rmad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H27 N O4, C H2 Cl2'
_chemical_formula_sum            'C28 H29 Cl2 N O4'
_chemical_formula_weight         514.42
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           78
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      78
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-12-04T10:31:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4707(5)
_cell_length_b                   11.4707(5)
_cell_length_c                   19.7124(18)
_cell_measurement_reflns_used    1999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.76
_cell_measurement_wavelength     0.71073
_cell_volume                     2593.7(3)
_computing_cell_refinement       'BRUKER APEXII'
_computing_data_collection       'BRUKER APEXII'
_computing_data_reduction        'BRUKER XPREP'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'BRUKER APPEX-II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20600
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.8439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3174
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6433
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.0932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                5351
_reflns_number_total             6433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0712827si20070227_041430.cif
_cod_data_source_block           sa13si2n
_cod_database_code               4109510