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_4034817
_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         'C19 H19 N3 O8 S, 0.5(H2 O)'
_chemical_formula_sum            'C19 H20 N3 O8.5 S'
_chemical_formula_weight         458.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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                90
_cell_angle_beta                 99.598(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.4510(9)
_cell_length_b                   7.5260(2)
_cell_length_c                   20.2835(7)
_cell_measurement_reflns_used    5625
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7700
_cell_measurement_theta_min      3.1240
_cell_volume                     3981.3(2)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -25.00   65.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -90.0000 90

  2 omega   -7.00   93.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000   30.0000 100

  3 omega   34.00   84.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000   90.0000 50

  4 omega  -67.00   23.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241    0.0000 -120.0000 90

  5 omega  -93.00  -67.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000 -180.0000 26

  6 omega    8.00   52.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000  -30.0000 44

  7 omega    2.00   38.00   1.0000   20.5100
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000  -60.0000 36
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0071455000
_diffrn_orient_matrix_UB_12      -0.0355032000
_diffrn_orient_matrix_UB_13      0.0326302000
_diffrn_orient_matrix_UB_21      0.0079303000
_diffrn_orient_matrix_UB_22      0.0855575000
_diffrn_orient_matrix_UB_23      0.0122291000
_diffrn_orient_matrix_UB_31      -0.0250158000
_diffrn_orient_matrix_UB_32      0.0169950000
_diffrn_orient_matrix_UB_33      0.0067419000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16967
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.766
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98275
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       prism
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0302P)^2^+5.8552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0824
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4045
_reflns_number_total             4578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00811_si_002.cif
_cod_data_source_block           ulm474
_cod_original_formula_sum        'C19 H20 N3 O8.50 S'
_cod_database_code               4034817
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C19 h19 n3 o8 s1'
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.927
_reflns_odcompleteness_completeness 99.89
_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, All O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H1S(0.5) H1SA(0.5)
3.a Free rotating group:
 O1S(H1S,H1SA)
3.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
3.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C24(H24), C21(H21), C19(H19), C23(H23), C22(H22), C17(H17), C18(H18)
3.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C28(H28A,H28B,H28C)
3.f Idealised tetrahedral OH refined as rotating group:
 O10(H10)
;
_shelx_res_checksum              30141
_shelx_hkl_checksum              90283
_shelx_fab_checksum              45237
_olex2_submission_special_instructions 'No special instructions were received'