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_4034814
_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         'C23 H24 F N3 O4'
_chemical_formula_sum            'C23 H24 F N3 O4'
_chemical_formula_weight         425.45
_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
_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                 97.968(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4745(4)
_cell_length_b                   16.8109(5)
_cell_length_c                   9.1460(3)
_cell_measurement_reflns_used    5467
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.8840
_cell_measurement_theta_min      3.2760
_cell_volume                     2051.74(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -90.00  -32.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -22.5803    0.0000 -180.0000 58

  2 omega  -89.00  -48.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -22.5803 -178.0000 -150.0000 41

  3 omega  -81.00   13.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -19.0000   60.0000 94

  4 omega   60.00   92.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       23.5178 -178.0000  -30.0000 32

  5 omega  -59.00  -32.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  178.0000  -30.0000 27

  6 omega  -77.00  -51.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -22.5803 -178.0000  120.0000 26

  7 omega   29.00   74.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       23.5178   57.0000   60.0000 45

  8 omega   48.00   78.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       23.5178  178.0000 -120.0000 30

  9 omega  -20.00   30.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       23.5178   19.0000   60.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0399329000
_diffrn_orient_matrix_UB_12      -0.0272223000
_diffrn_orient_matrix_UB_13      0.0189710000
_diffrn_orient_matrix_UB_21      0.0072822000
_diffrn_orient_matrix_UB_22      0.0151057000
_diffrn_orient_matrix_UB_23      0.0731252000
_diffrn_orient_matrix_UB_31      -0.0343077000
_diffrn_orient_matrix_UB_32      -0.0284653000
_diffrn_orient_matrix_UB_33      0.0207225000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.811
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96740
_exptl_absorpt_correction_type   multi-scan
_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)
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    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0436P)^2^+0.8271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4044
_reflns_number_total             4711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00811_si_004.cif
_cod_data_source_block           103-428-5970_ulm401
_cod_original_cell_volume        2051.75(11)
_cod_database_code               4034814
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C23 H24 F N3 O4'
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B), C3(H3A,H3B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C25(H25), C28(H28), C19(H19), C22(H22), C20(H20), C24(H24), C27(H27)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              21638
_shelx_hkl_checksum              88811
_olex2_submission_special_instructions 'No special instructions were received'