Bridged bicyclic peptides as potential drug scaffolds: synthesis, structure, protein binding and stability
Bartoloni, Marco; Jin, Xian; Marcaida, Maria José; Banha, João; Dibonaventura, Ivan; Bongoni, Swathi; Bartho, Kathrin; Gräbner, Olivia; Sefkow, Michael; Darbre, Tamis; Reymond, Jean-Louis; Chem. Sci. 6 (2015) 5473–; doi:10.1039/C5SC01699A

data_1529067
_publ_section_title
;
 Bridged bicyclic peptides as potential drug scaffolds: synthesis,
 structure, protein binding and stability
;
_journal_issue                   10
_journal_name_full               'Chem. Sci.'
_journal_page_first              5473
_journal_paper_doi               10.1039/C5SC01699A
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_sum            'C39 H64 N8 O12'
_chemical_formula_weight         836.98
_chemical_name_systematic
;
 ?
;
_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   mixed
_audit_creation_date             2015-05-07T13:27:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-05-07 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.755(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7309(7)
_cell_length_b                   9.6245(3)
_cell_length_c                   26.2360(10)
_cell_measurement_reflns_used    5335
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.701
_cell_measurement_theta_min      1.633
_cell_volume                     4263.9(3)
_computing_cell_refinement
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0965
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0383967
_diffrn_orient_matrix_UB_12      -0.02913
_diffrn_orient_matrix_UB_13      0.0102361
_diffrn_orient_matrix_UB_21      0.0082079
_diffrn_orient_matrix_UB_22      0.0180784
_diffrn_orient_matrix_UB_23      -0.0239949
_diffrn_orient_matrix_UB_31      0.0148915
_diffrn_orient_matrix_UB_32      0.0652186
_diffrn_orient_matrix_UB_33      0.01122
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.1311
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            40797
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.702
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
;
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       prism
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.3919
_exptl_crystal_size_mid          0.0532
_exptl_crystal_size_min          0.0426
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 3175 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1084
_refine_ls_number_reflns         15995
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1477
_refine_ls_R_factor_gt           0.0918
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1105P)^2^+2.6353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.253
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                9918
_reflns_number_total             15995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc01699a2.cif
_cod_data_source_block           13jlr008
_cod_depositor_comments
'Adding full bibliography for 1529064--1529068.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1529067