Synthesis and structure of 1,4-dipiperazino benzenes: chiral terphenyl-type peptide helix mimetics.
Maity, Prantik; König, Burkhard; Organic letters 10 (2008) 1473–1476; doi:10.1021/ol8002749

data_1504611
_publ_section_title
;
 Synthesis and structure of 1,4-dipiperazino benzenes: chiral
 terphenyl-type peptide helix mimetics.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1473
_journal_page_last               1476
_journal_paper_doi               10.1021/ol8002749
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C17 H32 N4, 2(H2 O), 4(Br H), Br, 2(O)'
_chemical_formula_sum            'C17 H40 Br5 N4 O4'
_chemical_formula_weight         764.03
_chemical_name_systematic        ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 108.420(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.3614(4)
_cell_length_b                   6.9622(2)
_cell_length_c                   14.6044(4)
_cell_measurement_reflns_used    11473
_cell_measurement_temperature    123
_cell_measurement_theta_max      62.1717
_cell_measurement_theta_min      3.1795
_cell_volume                     1385.43(7)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-05-2006 CrysAlis171 .NET)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
;
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.5431
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -76.00  -23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       -1.2571  -45.0000  120.0000    0.0000    0.0000 53

  2 phi     88.00  150.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000   -1.2571    0.0000     -        0.0000    0.0000 62

  3 omega  -79.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       -1.2571  -75.0000  120.0000    0.0000    0.0000 58

  4 omega  -72.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071  -45.0000  240.0000    0.0000    0.0000 53

  5 omega   24.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071   45.0000    0.0000    0.0000    0.0000 53

  6 omega  -72.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071  -45.0000    0.0000    0.0000    0.0000 53

  7 omega  -25.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071   45.0000    0.0000    0.0000    0.0000 53

  8 omega   23.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071   75.0000    0.0000    0.0000    0.0000 57

  9 omega  -25.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071   45.0000  240.0000    0.0000    0.0000 53

 10 omega  -31.00   27.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071   75.0000  120.0000    0.0000    0.0000 58

 11 omega  -25.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071   45.0000  120.0000    0.0000    0.0000 53

 12 phi    -62.00    2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000    2.5071    0.0000     -        0.0000    0.0000 64

 13 omega   23.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071   75.0000  120.0000    0.0000    0.0000 57

 14 omega -106.00  -51.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -75.0000  120.0000    0.0000    0.0000 55

 15 omega -108.00  -56.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -45.0000  120.0000    0.0000    0.0000 52

 16 omega -108.00  -57.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -41.0000  177.0000    0.0000    0.0000 51

 17 omega -115.00  -58.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   75.0000    0.0000    0.0000    0.0000 57

 18 omega -107.00  -50.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -75.0000  240.0000    0.0000    0.0000 57

 19 omega -117.00  -61.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  114.0000   12.0000    0.0000    0.0000 56

 20 omega -107.00  -54.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -60.0000   71.0000    0.0000    0.0000 53

 21 omega -116.00  -58.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   75.0000  120.0000    0.0000    0.0000 58

 22 omega -106.00  -53.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -65.0000  180.0000    0.0000    0.0000 53

 23 omega -158.00 -104.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -45.0000  285.0000    0.0000    0.0000 54

 24 omega -156.00 -103.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -55.0000   49.0000    0.0000    0.0000 53

 25 phi     -2.00   62.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 64

 26 omega  -60.00   -9.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   45.0000  240.0000    0.0000    0.0000 51

 27 omega -102.00  -56.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -45.0000  240.0000    0.0000    0.0000 46

 28 omega -160.00 -103.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -75.0000  120.0000    0.0000    0.0000 57

 29 omega -158.00 -104.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -45.0000  240.0000    0.0000    0.0000 54

 30 omega -107.00  -50.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -75.0000    0.0000    0.0000    0.0000 57

 31 omega -107.00  -56.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -45.0000  285.0000    0.0000    0.0000 51

 32 omega -116.00  -58.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   75.0000  240.0000    0.0000    0.0000 58

 33 omega  -62.00   -5.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   75.0000  240.0000    0.0000    0.0000 57

 34 omega -112.00  -67.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  112.0000  154.0000    0.0000    0.0000 45

 35 omega  -56.00  -28.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  114.0000   12.0000    0.0000    0.0000 28

 36 omega -107.00  -54.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -55.0000   49.0000    0.0000    0.0000 53

 37 omega  -61.00   -8.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   45.0000    0.0000    0.0000    0.0000 53

 38 omega  -61.00   -6.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   75.0000    0.0000    0.0000    0.0000 55

 39 omega -107.00  -54.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -52.0000   23.0000    0.0000    0.0000 53

 40 omega -159.00 -105.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -41.0000  177.0000    0.0000    0.0000 54

 41 omega   55.00  108.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   60.0000  -63.0000    0.0000    0.0000 53

 42 omega  106.00  134.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   54.0000  186.0000    0.0000    0.0000 28

 43 omega   63.00  111.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933  -45.0000    0.0000    0.0000    0.0000 48

 44 omega   55.00  108.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   60.0000  207.0000    0.0000    0.0000 53

 45 omega  105.00  158.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   52.0000   47.0000    0.0000    0.0000 53

 46 omega   10.00   57.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933  -45.0000  120.0000    0.0000    0.0000 47

 47 omega   51.00  109.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   75.0000  -74.0000    0.0000    0.0000 58

 48 omega   54.00  109.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   62.0000  217.0000    0.0000    0.0000 55

 49 omega   56.00  110.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   51.0000  174.0000    0.0000    0.0000 54

 50 omega   10.00   63.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933  -45.0000  240.0000    0.0000    0.0000 53

 51 omega   51.00  109.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   75.0000    0.0000    0.0000    0.0000 58

 52 omega   51.00  109.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   75.0000  240.0000    0.0000    0.0000 58

 53 omega   56.00   84.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   54.0000  186.0000    0.0000    0.0000 28

 54 omega   57.00   85.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   52.0000   47.0000    0.0000    0.0000 28

 55 omega  107.00  135.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   50.0000  -16.0000    0.0000    0.0000 28

 56 omega   56.00  110.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   50.0000  -16.0000    0.0000    0.0000 54

 57 omega   55.00  109.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   63.0000    0.0000    0.0000    0.0000 54

 58 omega   51.00  109.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   75.0000  120.0000    0.0000    0.0000 58

 59 omega  106.00  134.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   75.0000  -74.0000    0.0000    0.0000 28

 60 omega   57.00   85.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   52.0000   61.0000    0.0000    0.0000 28

 61 omega   57.00  110.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   45.0000    0.0000    0.0000    0.0000 53

 62 omega   57.00  108.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   58.0000  195.0000    0.0000    0.0000 51

 63 omega   51.00  109.00   1.0000    2.2000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   73.0000  -76.0000    0.0000    0.0000 58

;
_diffrn_measurement_device_type  'Oxford Diffraction Gemini Ultra'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26761
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        62.19
_diffrn_reflns_theta_max         62.19
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.017
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       'thin rectangular plate'
_exptl_crystal_F_000             754
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.515
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0436P)^2^]         where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                3576
_reflns_number_total             4284
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol8002749-file005.cif
_cod_data_source_block           g253
_cod_depositor_comments
;
The following automatic conversions were performed:
'__cell_measurement_reflns_used' tag replaced with
'_cell_measurement_reflns_used'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1504611