A Synthetic Strategy for the Preparation of Cyclic Peptide Mimetics Based on SET-Promoted Photocyclization Processes
Ung Chan Yoon; Ying Xue Jin; Sun Wha Oh; Chan Hyo Park; Jong Hoon Park; Charles F. Campana; Xiaolu Cai; Eileen N. Duesler; Patrick S. Mariano; Journal of the American Chemical Society 125 (2003) 10664–10671; doi:10.1021/ja030297b

data_4114105
_publ_section_title
;
 A Synthetic Strategy for the Preparation of Cyclic Peptide Mimetics Based
 on SET-Promoted Photocyclization Processes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10664
_journal_page_last               10671
_journal_paper_doi               10.1021/ja030297b
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C38 H38 N4 O5'
_chemical_formula_weight         630.72
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   10.2589(13)
_cell_length_b                   13.3262(12)
_cell_length_c                   24.287(3)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.51
_cell_measurement_theta_min      1.69
_cell_volume                     3320.3(7)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15634
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.68
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment
;
 all hydrogen atoms seen after all nonH anisotropic; H on C in
 ideal positions [riding model] with fixed isoU=1.25U[equiv] and
 H on O vary in position and iso U gave wR2 9.06%, R1,all=5.02%
 R1,obs=3.65% with 428 parms, checkcif objected H15b..H32a=1.99A.
 allowing CH2 and CH3 h atoms to vary in positions increased
 parm to 482 but also fixed this problem [wR2=8.77%,R1,all 4.97%,
 R1,obs=3.59%...slight improvement]; this problem is seen
 in related cmps [Pm021,Pm022 with H[C] in idealized positions]--
 just a little relaxation of tetrahedral geometries will eliminate
 the problem. checkcif passed this last improvement and it was used.
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         5830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0432P)^2^+0.0917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                4737
_reflns_number_total             5830
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja030297b_3.cif
_cod_data_source_block           Comp-58/pm032
_cod_original_cell_volume        3320.3(6)
_cod_database_code               4114105