Synthesis and structure of symmetrical bicyclic hexapeptides bridged by metathesis reaction.
Giovannoni, Jérôme; Didierjean, Claude; Durand, Philippe; Marraud, Michel; Aubry, André; Renaut, Patrice; Martinez, Jean; Amblard, Muriel; Organic letters 6 (2004) 3449–3452; doi:10.1021/ol0487940

data_1507035
_publ_section_title
;
 Synthesis and structure of symmetrical bicyclic hexapeptides bridged by
 metathesis reaction.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              3449
_journal_page_last               3452
_journal_paper_doi               10.1021/ol0487940
_journal_volume                  6
_journal_year                    2004
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C36 H42 N6 O6, 5H2O'
_chemical_formula_sum            'C36 H52 N6 O11'
_chemical_formula_weight         744.84
_chemical_name_systematic
; 
(20E,1S,4R,7S,10S,13R,16S)-4,13-dibenzyl-7,8,16,17-
di(propane-1,3-diyl)-2,5,8,11,14,17-hexaaza-
bicyclo[8.8.4]docos-20-ene-3,6,9,12,15,18-hexaone
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-03-05T14:43:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.4080(10)
_cell_length_b                   15.8690(10)
_cell_length_c                   9.5910(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.76
_cell_measurement_theta_min      7.95
_cell_measurement_wavelength     1.5406
_cell_volume                     2040.7(3)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'WebLab ViewerPro 3.5 (MSI, 1999)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR_92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Mach3 diffractometer'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nonius FR591 rotating Cu anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2148
_diffrn_reflns_theta_full        69.51
_diffrn_reflns_theta_max         69.51
_diffrn_reflns_theta_min         4.31
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.75
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.08
_refine_ls_abs_structure_details
;
The absolute conformation was not determined 
from the diffraction experiment since it was known 
from the synthetic experiment.
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2148
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.22
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1231P)^2^+0.6136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1731
_reflns_number_gt                2021
_reflns_number_total             2148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0487940si20040624_093911.cif
_cod_data_source_block           shelxl
_cod_database_code               1507035