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_4034818
_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 H23 N3 O4'
_chemical_formula_sum            'C26 H23 N3 O4'
_chemical_formula_weight         441.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9764(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6746(2)
_cell_length_b                   17.7585(3)
_cell_length_c                   8.82977(16)
_cell_measurement_reflns_used    7364
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0380
_cell_measurement_theta_min      3.2340
_cell_volume                     2117.96(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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -66.00  23.00   1.00    1.30    --  -40.38  38.00  90.00   89
  2  \w    -43.00  21.00   1.00    1.30    --  -40.38  38.00 150.00   64
  3  \w     94.00 125.00   1.00    1.30    --   40.38 178.00-150.00   31
  4  \w    147.00 178.00   1.00    5.00    --  113.00  94.00-122.00   31
  5  \w    118.00 144.00   1.00    5.00    --  113.00 112.00 -60.00   26
  6  \w    103.00 135.00   1.00    5.00    --  113.00  94.00-122.00   32
  7  \w    101.00 144.00   1.00    5.00    --  113.00 112.00-180.00   43
  8  \w    140.00 175.00   1.00    5.00    --  113.00  15.00  60.00   35
  9  \w     73.00 112.00   1.00    5.00    --  113.00-112.00  30.00   39
 10  \w     66.00 144.00   1.00    5.00    --  113.00 -77.00 150.00   78
 11  \w     55.00 128.00   1.00    1.30    --   40.38-178.00  30.00   73
 12  \w     32.00 107.00   1.00    5.00    --  113.00 -95.00  90.00   75
 13  \w     35.00  61.00   1.00    5.00    --  113.00-112.00 120.00   26
 14  \w     53.00 122.00   1.00    5.00    --  113.00  15.00  60.00   69
 15  \w     30.00 109.00   1.00    5.00    --  113.00 -95.00 -60.00   79
 16  \w   -113.00 -16.00   1.00    1.30    --  -40.38 -57.00 -60.00   97
 17  \w    -61.00  10.00   1.00    1.30    --  -40.38  38.00-120.00   71
 18  \w     61.00  87.00   1.00    1.30    --   40.38 178.00-180.00   26
 19  \w     12.00  38.00   1.00    1.30    --   40.38 -99.00 -90.00   26
 20  \w     79.00 105.00   1.00    5.00    --  113.00  77.00-180.00   26
 21  \w    119.00 153.00   1.00    5.00    --  113.00  77.00-180.00   34
 22  \w    121.00 168.00   1.00    5.00    --  113.00  45.00 -60.00   47
 23  \w    140.00 177.00   1.00    5.00    --  113.00  15.00-120.00   37
 24  \w    102.00 166.00   1.00    5.00    --  113.00 112.00 120.00   64
 25  \w    148.00 178.00   1.00    5.00    --  113.00  45.00   0.00   30
 26  \w     90.00 115.00   1.00    5.00    --  113.00-112.00 -90.00   25
 27  \w     94.00 119.00   1.00    5.00    --  113.00  61.00 -90.00   25
 28  \w     35.00  67.00   1.00    5.00    --  113.00-112.00 -90.00   32
 29  \w     69.00 113.00   1.00    5.00    --  113.00-112.00 150.00   44
 30  \w     45.00 129.00   1.00    5.00    --  113.00 -45.00  90.00   84
 31  \w    131.00 157.00   1.00    5.00    --  113.00  61.00 -90.00   26
 32  \w    151.00 178.00   1.00    5.00    --  113.00  15.00 120.00   27
 33  \w     39.00  90.00   1.00    5.00    --  113.00 -95.00  30.00   51
 34  \w     59.00  85.00   1.00    5.00    --  113.00  15.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0071383000
_diffrn_orient_matrix_UB_12      0.0805574000
_diffrn_orient_matrix_UB_13      0.0621233000
_diffrn_orient_matrix_UB_21      0.1136141000
_diffrn_orient_matrix_UB_22      0.0030388000
_diffrn_orient_matrix_UB_23      0.0416914000
_diffrn_orient_matrix_UB_31      0.0071346000
_diffrn_orient_matrix_UB_32      0.0320483000
_diffrn_orient_matrix_UB_33      -0.1600108000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19212
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.227
_diffrn_reflns_theta_min         3.272
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64833
_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    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0589P)^2^+0.9916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3651
_reflns_number_total             4375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00811_si_006.cif
_cod_data_source_block           ulm386
_cod_original_cell_volume        2117.96(7)
_cod_database_code               4034818
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'c26 h23 n4 o4'
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.855
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C30(H30), C31(H31), C17(H17), C28(H28), C24(H24), C26(H26), C21(H21),
 C22(H22), C27(H27), C18(H18), C19(H19), C25(H25), C23(H23), C20(H20)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_shelx_res_checksum              57759
_shelx_hkl_checksum              34601
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.501
_oxdiff_exptl_absorpt_empirical_full_min 0.279