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_4034819
_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         'C21 H23 N2 O7, H2 O'
_chemical_formula_sum            'C21 H24 N2 O8'
_chemical_formula_weight         432.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_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                 95.330(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8791(3)
_cell_length_b                   16.7820(7)
_cell_length_c                   8.8948(4)
_cell_measurement_reflns_used    3066
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4720
_cell_measurement_theta_min      3.1920
_cell_volume                     1022.42(8)
_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)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -97.00  -65.00   1.0000    4.2700
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000   60.0000 32

  2 omega   -7.00   85.00   1.0000    4.2700
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  -30.0000 92

  3 omega  -39.00    4.00   1.0000    4.2700
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -77.0000 -180.0000 43

  4 omega   22.00   50.00   1.0000    4.2700
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -77.0000 -180.0000 28

  5 omega  -46.00   -6.00   1.0000    4.2700
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -77.0000  -60.0000 40

  6 omega   30.00   70.00   1.0000    4.2700
omega____ theta____ kappa____ phi______ frames
    -       23.3616    0.0000  -30.0000 40

  7 omega   -6.00   91.00   1.0000    4.2700
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  150.0000 97

  8 omega    4.00   64.00   1.0000    4.2700
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000   90.0000 60

  9 omega  -41.00  -15.00   1.0000    4.2700
omega____ theta____ kappa____ phi______ frames
    -       23.3616    0.0000  -30.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0028551000
_diffrn_orient_matrix_UB_12      0.0067313000
_diffrn_orient_matrix_UB_13      0.0788903000
_diffrn_orient_matrix_UB_21      -0.0045397000
_diffrn_orient_matrix_UB_22      -0.0416840000
_diffrn_orient_matrix_UB_23      0.0124800000
_diffrn_orient_matrix_UB_31      0.1034097000
_diffrn_orient_matrix_UB_32      -0.0020282000
_diffrn_orient_matrix_UB_33      0.0057978000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_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            8617
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.974
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97752
_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    1.405
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0402P)^2^+0.1669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0823
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.796
_reflns_number_gt                3577
_reflns_number_total             3815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00811_si_001.cif
_cod_data_source_block           103-428-7350_ulm671
_cod_database_code               4034819
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C21 H22 N2 O7'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.971
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB)
2.b Ternary CH refined with riding coordinates:
 C3(H3), C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C6(H6A,H6B), C28(H28A,H28B)
2.d Aromatic/amide H refined with riding coordinates:
 C17(H17), C19(H19), C22(H22), C18(H18), C13(H13), C14(H14)
2.e Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C29(H29A,H29B,H29C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              24991
_shelx_hkl_checksum              68120
_olex2_submission_special_instructions 'No special instructions were received'