Synthesis and evaluation of a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane scaffold as a mimic of Xaa-trans-Pro in poly-l-proline type II helix conformation.
Aillard, Boris; Kilburn, Jeremy D.; Blaydes, Jeremy P.; Tizzard, Graham J.; Findlow, Stuart; Werner, Jörn M; Bloodworth, Sally; Organic & biomolecular chemistry 13 (2015) 4562–4569; doi:10.1039/c5ob00180c

data_7154369
_publ_section_title
;
 Synthesis and evaluation of a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane
 scaffold as a mimic of Xaa-trans-Pro in poly-l-proline type II helix
 conformation.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4562
_journal_page_last               4569
_journal_paper_doi               10.1039/c5ob00180c
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H36 N4 O7, C10 H17 N2 O3, Cl, H2 O'
_chemical_formula_sum            'C34 H55 Cl N6 O11'
_chemical_formula_weight         759.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   constr
_atom_sites_solution_primary     dual
_audit_creation_date             2014-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2014-07-17 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.441(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.568(15)
_cell_length_b                   7.443(7)
_cell_length_c                   19.72(2)
_cell_measurement_reflns_used    3531
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      2.0
_cell_volume                     1920(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
scan:
    Number of images: 175
               Slice: -60.0000 - 115.0000
         Image width: 1.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 0.0000
                 XTD: 59.5342
              2theta: 30.2482
scan:
    Number of images: 120
               Slice: -60.0000 - 60.0000
         Image width: 1.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -50.0000
                 Phi: 0.0000
                 XTD: 59.5342
              2theta: 30.2482
scan:
    Number of images: 120
               Slice: -60.0000 - 60.0000
         Image width: 1.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -50.0000
                 Phi: 120.0000
                 XTD: 59.5342
              2theta: 30.2482
scan:
    Number of images: 120
               Slice: -60.0000 - 60.0000
         Image width: 1.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -50.0000
                 Phi: 240.0000
                 XTD: 59.5342
              2theta: 30.2482
;
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.005784
_diffrn_orient_matrix_UB_12      0.046308
_diffrn_orient_matrix_UB_13      0.060569
_diffrn_orient_matrix_UB_21      -0.131889
_diffrn_orient_matrix_UB_22      0.024792
_diffrn_orient_matrix_UB_23      -0.006359
_diffrn_orient_matrix_UB_31      -0.007807
_diffrn_orient_matrix_UB_32      -0.030770
_diffrn_orient_matrix_UB_33      0.041953
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.1905
_diffrn_reflns_av_unetI/netI     0.1677
_diffrn_reflns_Laue_measured_fraction_full 0.915
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15866
_diffrn_reflns_point_group_measured_fraction_full 0.790
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.290
_diffrn_reflns_theta_min         2.047
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       lath
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 586 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         5851
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.0833
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0670P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.2067
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_full    0.643
_reflns_Friedel_fraction_max     0.697
_reflns_number_gt                2849
_reflns_number_total             5851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00180c2.cif
_cod_data_source_block           2013ncs0778dlsa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 

 Adding full bibliography for 7154369.cif.
;
_cod_database_code               7154369
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O91(H91A,H91B)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C4(H4A), C7(H7), C10(H10), C13(H13), C16(H16), C32(H32), C35(H35),
 C38(H38)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C11(H11A,H11B), C12(H12A,
 H12B), C14(H14A,H14B), C15(H15A,H15B), C33(H33A,H33B), C34(H34A,H34B),
 C36(H36A,H36B), C37(H37A,H37B)
2.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), N32(H32A,H32B,H32C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              88381
_olex2_submission_special_instructions 'No special instructions were received'