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_4034815
_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         'C26 H21 F2 N3 O4'
_chemical_formula_sum            'C26 H21 F2 N3 O4'
_chemical_formula_weight         477.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-11-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.8212(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.53442(14)
_cell_length_b                   22.08306(16)
_cell_length_c                   14.82247(15)
_cell_measurement_reflns_used    41385
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0250
_cell_measurement_theta_min      3.5580
_cell_volume                     4352.20(8)
_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 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -40.00  -8.00   1.00    2.50    --  -40.38  57.00  30.00   32
  2  \w   -117.00 -12.00   1.00    2.50    --  -40.38 -77.00  60.00  105
  3  \w     14.00  45.00   1.00    2.50    --   40.38 -99.00-120.00   31
  4  \w     73.00 110.00   1.00    8.00    --  113.00-112.00-120.00   37
  5  \w     77.00 103.00   1.00    8.00    --  113.00-112.00 -60.00   26
  6  \w     59.00  94.00   1.00    8.00    --  113.00-112.00-180.00   35
  7  \w     35.00  73.00   1.00    8.00    --  113.00-112.00 -60.00   38
  8  \w     31.00  59.00   1.00    8.00    --  113.00 -95.00  60.00   28
  9  \w     81.00 106.00   1.00    8.00    --  113.00 -95.00  60.00   25
 10  \w     43.00 115.00   1.00    8.00    --  113.00-112.00 150.00   72
 11  \w     37.00 141.00   1.00    8.00    --  113.00 -30.00  90.00  104
 12  \w    125.00 172.00   1.00    8.00    --  113.00  45.00 -60.00   47
 13  \w    121.00 168.00   1.00    8.00    --  113.00  45.00 -90.00   47
 14  \w    103.00 177.00   1.00    8.00    --  113.00 112.00-150.00   74
 15  \w     86.00 113.00   1.00    8.00    --  113.00  45.00 -90.00   27
 16  \w    152.00 177.00   1.00    8.00    --  113.00 112.00  60.00   25
 17  \w   -129.00 -35.00   1.00    2.50    --  -40.38-178.00-150.00   94
 18  \w   -105.00 -44.00   1.00    2.50    --  -40.38 -38.00-180.00   61
 19  \w    -72.00 -46.00   1.00    2.50    --  -40.38 178.00 -60.00   26
 20  \w    -49.00  30.00   1.00    2.50    --  -40.38  57.00-180.00   79
 21  \w     94.00 120.00   1.00    2.50    --   40.38 178.00 -90.00   26
 22  \w     30.00  56.00   1.00    8.00    --  113.00 -95.00 120.00   26
 23  \w    119.00 145.00   1.00    8.00    --  113.00 112.00 120.00   26
 24  \w    115.00 144.00   1.00    8.00    --  113.00 -77.00-150.00   29
 25  \w     90.00 115.00   1.00    8.00    --  113.00-112.00 -30.00   25
 26  \w     77.00 103.00   1.00    8.00    --  113.00 -77.00-150.00   26
 27  \w     47.00  98.00   1.00    8.00    --  113.00-112.00-150.00   51
 28  \w     37.00  62.00   1.00    8.00    --  113.00-112.00 -30.00   25
 29  \w    127.00 175.00   1.00    8.00    --  113.00 112.00-180.00   48
 30  \w     37.00  67.00   1.00    8.00    --  113.00 -77.00-150.00   30
 31  \w    153.00 178.00   1.00    8.00    --  113.00 112.00 120.00   25
 32  \w     82.00 178.00   1.00    8.00    --  113.00  30.00-180.00   96
 33  \w    109.00 173.00   1.00    8.00    --  113.00  45.00  60.00   64
 34  \w     87.00 113.00   1.00    8.00    --  113.00-112.00-120.00   26
 35  \w     41.00 127.00   1.00    8.00    --  113.00-135.00  71.61   86
 36  \w     94.00 120.00   1.00    2.50    --   40.38 178.00-180.00   26
 37  \w     47.00 114.00   1.00    2.50    --   40.38  38.00 -60.00   67
 38  \w     45.00  91.00   1.00    8.00    --  113.00 -30.00 -90.00   46
 39  \w    118.00 155.00   1.00    8.00    --  113.00 112.00   0.00   37
 40  \w    113.00 140.00   1.00    8.00    --  113.00 -30.00 -90.00   27
 41  \w    108.00 135.00   1.00    8.00    --  113.00 112.00  90.00   27
 42  \w    122.00 153.00   1.00    8.00    --  113.00  61.00  90.00   31
 43  \w     27.00  83.00   1.00    2.50    --   40.38-128.00 116.00   56
 44  \w      1.00  26.00   1.00    2.50    --   40.00  92.00-175.14   25
 45  \w    -56.00 -11.00   1.00    2.50    --  -40.38 -57.00  90.00   45
 46  \w   -114.00 -14.00   1.00    2.50    --  -40.38 -38.00-120.00  100
 47  \w      7.00  32.00   1.00    2.50    --   44.00  88.00  15.14   25
 48  \w     18.00  43.00   1.00    2.50    --   52.00  80.00 -71.98   25
 49  \w     17.00  42.00   1.00    2.50    --   52.00  82.00  47.38   25
 50  \w     17.00  42.00   1.00    2.50    --   52.00  81.00-111.14   25
 51  \w     17.00  42.00   1.00    2.50    --   52.00  82.00 133.40   25
 52  \w     22.00  47.00   1.00    2.50    --   56.00  78.00-164.10   25
 53  \w     22.00  47.00   1.00    2.50    --   56.00  78.00  74.11   25
 54  \w     30.00  55.00   1.00    2.50    --   64.00  77.00 118.30   25
 55  \w     31.00  57.00   1.00    2.50    --   64.00  75.00 -11.79   26
 56  \w     34.00  59.00   1.00    2.50    --   68.00  77.00 -68.04   25
 57  \w     35.00  61.00   1.00    2.50    --   68.00  77.00-165.95   26
 58  \w     35.00  61.00   1.00    2.50    --   68.00  76.00 -42.77   26
 59  \w     35.00  74.00   1.00    2.50    --   68.00  76.00 140.82   39
 60  \w     39.00  65.00   1.00    2.50    --   72.00  76.00  -6.69   26
 61  \w     38.00  64.00   1.00    2.50    --   72.00  77.00-105.71   26
 62  \w     38.00  64.00   1.00    2.50    --   72.00  77.00-149.89   26
 63  \w     38.00  64.00   1.00    2.50    --   72.00  77.00  46.23   26
 64  \w    104.00 130.00   1.00    2.50    --   72.00  77.00-105.71   26
 65  \w    118.00 144.00   1.00    8.00    --   80.00  68.00-126.97   26
 66  \w     47.00  73.00   1.00    8.00    --   80.00  73.00  24.54   26
 67  \w     48.00  74.00   1.00    8.00    --   80.00  72.00  72.33   26
 68  \w     49.00  75.00   1.00    8.00    --   80.00  68.00-126.97   26
 69  \w     47.00  78.00   1.00    8.00    --   80.00  73.00-174.67   31
 70  \w     52.00  78.00   1.00    8.00    --   84.00  71.00 -88.13   26
 71  \w     51.00 104.00   1.00    8.00    --   84.00  76.00  87.81   53
 72  \w     56.00  82.00   1.00    8.00    --   88.00  68.00 150.27   26
 73  \w     59.00  85.00   1.00    8.00    --   88.00  56.00  61.49   26
 74  \w     56.00  81.00   1.00    8.00    --   88.00  71.00 -10.13   25
 75  \w     58.00  84.00   1.00    8.00    --   92.00  77.00 -65.97   26
 76  \w     61.00  87.00   1.00    8.00    --   92.00  66.00 128.31   26
 77  \w     61.00  87.00   1.00    8.00    --   92.00  62.00 -60.99   26
 78  \w     61.00  86.00   1.00    8.00    --   92.00  66.00-113.99   25
 79  \w     93.00 137.00   1.00    8.00    --   96.00  74.00  63.99   44
 80  \w     63.00  89.00   1.00    8.00    --   96.00  74.00  63.99   26
 81  \w     63.00  88.00   1.00    8.00    --   96.00  74.00-168.27   25
 82  \w     63.00  90.00   1.00    8.00    --   96.00  76.00-124.22   27
 83  \w     68.00  93.00   1.00    8.00    --  100.00  70.00  10.97   25
 84  \w     75.00 101.00   1.00    8.00    --  108.00  73.00 -55.36   26
 85  \w     75.00 106.00   1.00    8.00    --  108.00  74.00 129.25   31
 86  \w     79.00 127.00   1.00    8.00    --  113.00  77.00 -90.00   48
 87  \w     80.00 107.00   1.00    8.00    --  113.00  76.00 130.03   27
 88  \w     84.00 111.00   1.00    8.00    --  113.00  61.00  30.00   27
 89  \w     79.00 146.00   1.00    8.00    --  113.00  77.00-150.00   67
 90  \w     79.00 141.00   1.00    8.00    --  113.00  77.00-180.00   62
 91  \w     84.00 136.00   1.00    8.00    --  113.00  61.00 -30.00   52
 92  \w     79.00 129.00   1.00    8.00    --  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  0.0484
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            90200
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.395
_diffrn_reflns_theta_min         3.595
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79380
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       prism
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         9064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+1.9564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7972
_reflns_number_total             9064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00811_si_005.cif
_cod_data_source_block           103-428-7385_ulm_581_prism
_cod_database_code               4034815
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.800
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9), C9A(H9A), C10A(H10A)
2.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C6(H6A,H6B), C3(H3A,H3B), C3A(H3AA,H3AB)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C21A(H21A), C21(H21), C30(H30), C17(H17), C22(H22), C20A(H20A),
 C20(H20), C31(H31), C27A(H27A), C22A(H22A), C27(H27), C26A(H26A), C17A(H17A),
 C28A(H28A), C18(H18), C18A(H18A), C25(H25), C28(H28), C23A(H23A), C23(H23),
 C31A(H31A), C25A(H25A), C30A(H30A)
2.d Idealised Me refined as rotating group:
 C33A(H33D,H33E,H33F), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              7685
_shelx_hkl_checksum              56467
_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
;