Bicyclic Piperazine Mimetics of the Peptide β-Turn Assembled via the Castagnoli-Cushman Reaction.
Usmanova, Liliia; Dar'in, Dmitry; Novikov, Mikhail S.; Gureev, Maxim; Krasavin, Mikhail; The Journal of organic chemistry 83 (2018) 5859–5868; doi:10.1021/acs.joc.8b00811

data_4034816
_publ_section_title
;
 Bicyclic Piperazine Mimetics of the Peptide \b-Turn Assembled via the
 Castagnoli-Cushman Reaction.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5859
_journal_page_last               5868
_journal_paper_doi               10.1021/acs.joc.8b00811
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H20 F N3 O3'
_chemical_formula_sum            'C17 H20 F N3 O3'
_chemical_formula_weight         333.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2017-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                89.339(3)
_cell_angle_beta                 77.612(3)
_cell_angle_gamma                80.243(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8496(3)
_cell_length_b                   10.1390(4)
_cell_length_c                   12.0844(4)
_cell_measurement_reflns_used    6902
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7540
_cell_measurement_theta_min      3.7120
_cell_volume                     807.57(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w      6.00  64.00   1.00    2.50    --   40.38 -99.00   0.00   58
  2  \w     48.00 144.00   1.00   10.00    --  113.00 -30.00 120.00   96
  3  \w     84.00 178.00   1.00   10.00    --  113.00  15.00   0.00   94
  4  \w    125.00 168.00   1.00   10.00    --  113.00  45.00 -90.00   43
  5  \w    104.00 131.00   1.00   10.00    --  113.00 112.00-180.00   27
  6  \w     84.00 128.00   1.00    2.50    --   40.38 178.00 -60.00   44
  7  \w    123.00 175.00   1.00   10.00    --  113.00 112.00 120.00   52
  8  \w     38.00 104.00   1.00   10.00    --  113.00 -45.00-120.00   66
  9  \w     70.00  98.00   1.00   10.00    --  113.00 -95.00 -30.00   28
 10  \w     47.00 137.00   1.00   10.00    --  113.00 -77.00  60.00   90
 11  \w     43.00 139.00   1.00   10.00    --  113.00 -30.00   0.00   96
 12  \w     90.00 115.00   1.00   10.00    --  113.00-112.00-180.00   25
 13  \w     49.00  95.00   1.00   10.00    --  113.00 -95.00-150.00   46
 14  \w     39.00  64.00   1.00   10.00    --  113.00-112.00-180.00   25
 15  \w     35.00  98.00   1.00   10.00    --  113.00 -95.00 -90.00   63
 16  \w     35.00 112.00   1.00   10.00    --  113.00-112.00  60.00   77
 17  \w    -63.00 -37.00   1.00    2.50    --  -40.38 178.00 -90.00   26
 18  \w   -113.00 -17.00   1.00    2.50    --  -40.38 -57.00-120.00   96
 19  \w   -115.00 -16.00   1.00    2.50    --  -40.38 -38.00 120.00   99
 20  \w   -121.00 -43.00   1.00    2.50    --  -40.38 178.00 -30.00   78
 21  \w    -61.00  24.00   1.00    2.50    --  -40.38  38.00 -60.00   85
 22  \w   -116.00 -14.00   1.00    2.50    --  -40.38 -38.00 -60.00  102
 23  \w     12.00  38.00   1.00    2.50    --   48.00  84.00 131.35   26
 24  \w     12.00  37.00   1.00    2.50    --   48.00  84.00-138.32   25
 25  \w     18.00  43.00   1.00    2.50    --   52.00  80.00  33.04   25
 26  \w     17.00  42.00   1.00    2.50    --   52.00  81.00 -80.64   25
 27  \w     17.00  44.00   1.00    2.50    --   52.00  82.00 -26.56   27
 28  \w     33.00  59.00   1.00    2.50    --   64.00  76.00  71.97   26
 29  \w     31.00  69.00   1.00    2.50    --   64.00  76.00 110.94   38
 30  \w     97.00 140.00   1.00    2.50    --   64.00  76.00 -79.17   43
 31  \w     32.00  58.00   1.00    2.50    --   64.00  76.00 -79.17   26
 32  \w     34.00  65.00   1.00    2.50    --   68.00  77.00-121.77   31
 33  \w    107.00 144.00   1.00    2.50    --   68.00  70.00 -19.56   37
 34  \w     38.00  63.00   1.00    2.50    --   68.00  70.00 -19.56   25
 35  \w     36.00  62.00   1.00    2.50    --   68.00  75.00 169.75   26
 36  \w     35.00  64.00   1.00    2.50    --   68.00  75.00  21.03   29
 37  \w     39.00  70.00   1.00    2.50    --   72.00  76.00  38.17   31
 38  \w     44.00  77.00   1.00    2.50    --   72.00  60.00-151.81   33
 39  \w     43.00  74.00   1.00    2.50    --   76.00  72.00  81.94   31
 40  \w     57.00  93.00   1.00   10.00    --   88.00  71.00 -72.56   36
 41  \w     79.00 105.00   1.00   10.00    --  113.00  77.00 -30.00   26
 42  \w    120.00 146.00   1.00   10.00    --  113.00  77.00  60.00   26
 43  \w     79.00 112.00   1.00   10.00    --  113.00  77.00  60.00   33
 44  \w     83.00 131.00   1.00   10.00    --  113.00  61.00-120.00   48
 45  \w     87.00 114.00   1.00   10.00    --  113.00  61.00 -60.00   27
 46  \w     79.00 153.00   1.00   10.00    --  113.00  77.00 120.00   74
 47  \w     80.00 118.00   1.00   10.00    --  113.00  77.00-180.00   38
 48  \w     83.00 123.00   1.00   10.00    --  113.00  61.00 -90.00   40
 49  \w     85.00 111.00   1.00   10.00    --  113.00  61.00 -30.00   26
 50  \w     81.00 139.00   1.00   10.00    --  113.00  77.00   0.00   58
 51  \w     79.00 105.00   1.00   10.00    --  113.00  77.00 -90.00   26
 52  \w     86.00 142.00   1.00   10.00    --  113.00  61.00  90.00   56
 53  \w     87.00 129.00   1.00   10.00    --  113.00  61.00 120.00   42
 54  \w     84.00 111.00   1.00   10.00    --  113.00  61.00   0.00   27
 55  \w    125.00 151.00   1.00   10.00    --  113.00  77.00 150.00   26
 56  \w     85.00 159.00   1.00   10.00    --  113.00  45.00-180.00   74
 57  \w     79.00 105.00   1.00   10.00    --  113.00  77.00 150.00   26
 58  \w     79.00 116.00   1.00   10.00    --  113.00  77.00-150.00   37
 59  \w     79.00 105.00   1.00   10.00    --  113.00  77.00 -60.00   26
 60  \w    133.00 166.00   1.00   10.00    --  113.00  77.00  90.00   33
 61  \w     85.00 110.00   1.00   10.00    --  113.00  61.00  30.00   25
 62  \w     79.00 129.00   1.00   10.00    --  113.00  77.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13308
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.482
_diffrn_reflns_theta_min         3.746
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0460P)^2^+0.2734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2857
_reflns_number_total             3213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00811_si_007.cif
_cod_data_source_block           103-428-7402_ulm684
_cod_database_code               4034816
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.777
_olex2_refinement_description
;
;
_shelx_res_checksum              66358
_shelx_hkl_checksum              7457
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;