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_4109505
_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        'Miguel. A. Miranda'
_publ_contact_author_phone       0034963877807
_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 ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H23 N O3'
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.4
_chemical_name_common            2004uv09sd02
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-05-19T11:50:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.792(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.207(2)
_cell_length_b                   27.329(7)
_cell_length_c                   15.559(2)
_cell_measurement_reflns_used    5686
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      65.089
_cell_measurement_theta_min      1.027
_cell_measurement_wavelength     1.5418
_cell_volume                     3374.1(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      120.0(1)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       '135mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD2000
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0319063
_diffrn_orient_matrix_UB_12      -0.0057036
_diffrn_orient_matrix_UB_13      -0.0656641
_diffrn_orient_matrix_UB_21      0.1218061
_diffrn_orient_matrix_UB_22      0
_diffrn_orient_matrix_UB_23      -0.0000695
_diffrn_orient_matrix_UB_31      0.0050349
_diffrn_orient_matrix_UB_32      -0.0361439
_diffrn_orient_matrix_UB_33      0.0103619
_diffrn_radiation_monochromator  'graded mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            38385
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        65.29
_diffrn_reflns_theta_max         65.29
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_correction_T_min  0.6279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(18)
_refine_ls_extinction_coef       0.0057(5)
_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   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     925
_refine_ls_number_reflns         11033
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0585
_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^)+(0.1023P)^2^+0.6425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                9307
_reflns_number_total             11033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0712827si20070227_040914.cif
_cod_data_source_block           2004uv09
_cod_original_cell_volume        3374.2(12)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4109505