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_1504609
_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         'C19 H23 Br N2'
_chemical_formula_sum            'C19 H23 Br N2'
_chemical_formula_weight         359.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2007(1)
_cell_length_b                   11.5462(1)
_cell_length_c                   16.0967(1)
_cell_measurement_reflns_used    13035
_cell_measurement_temperature    123
_cell_measurement_theta_max      62.0630
_cell_measurement_theta_min      2.7396
_cell_volume                     1710.00(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -31.00   27.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071   75.0000  240.0000    0.0000    0.0000 58

  2 phi     58.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000    2.5071    0.0000     -        0.0000    0.0000 64

  3 omega  -75.00  -17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        2.5071  -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  120.0000    0.0000    0.0000 53

  5 omega -157.00 -103.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -59.0000  241.0000    0.0000    0.0000 54

  6 omega -108.00  -55.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -45.0000  240.0000    0.0000    0.0000 53

  7 omega  -62.00   -5.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   75.0000  240.0000    0.0000    0.0000 57

  8 omega -114.00  -57.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  107.0000  197.0000    0.0000    0.0000 57

  9 omega -116.00  -58.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   75.0000    0.0000    0.0000    0.0000 58

 10 omega -121.00  -67.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  124.0000  282.0000    0.0000    0.0000 54

 11 omega  -62.00   -5.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433   75.0000    0.0000    0.0000    0.0000 57

 12 omega -159.00 -103.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -69.0000  185.0000    0.0000    0.0000 56

 13 omega -158.00 -104.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -83.1433  -45.0000  240.0000    0.0000    0.0000 54

 14 omega    7.00   65.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933  -75.0000    0.0000    0.0000    0.0000 58

 15 omega  104.00  159.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   65.0000   85.0000    0.0000    0.0000 55

 16 omega  105.00  159.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   62.0000  -10.0000    0.0000    0.0000 54

 17 omega  106.00  159.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   45.0000  120.0000    0.0000    0.0000 53

 18 omega   61.00  118.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933  -75.0000    0.0000    0.0000    0.0000 57

 19 omega    7.00   65.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933  -75.0000  120.0000    0.0000    0.0000 58

 20 omega   54.00  109.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   60.0000  192.0000    0.0000    0.0000 55

 21 omega   55.00  109.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   53.0000  166.0000    0.0000    0.0000 54

 22 omega   53.00  108.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       84.3933   65.0000   85.0000    0.0000    0.0000 55

 23 phi    -62.00    2.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 64

 24 phi   -122.00  -58.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 64

 25 phi     58.00  122.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 64

 26 phi     28.00   92.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 64

 27 phi    -92.00  -28.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 64

 28 phi    -32.00   32.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 64

 29 phi     -2.00   62.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 64

 30 phi    118.00  180.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 62

 31 phi   -150.00  -88.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
 -40.0000  -83.1433    0.0000     -        0.0000    0.0000 62

 32 phi     28.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000    2.5071    0.0000     -        0.0000    0.0000 64

 33 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

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

 35 phi   -122.00  -68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000    2.5071    0.0000     -        0.0000    0.0000 54

 36 phi     28.00   92.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000   84.3933    0.0000     -        0.0000    0.0000 64

 37 phi   -122.00  -58.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000   84.3933    0.0000     -        0.0000    0.0000 64

 38 phi     58.00  122.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000   84.3933    0.0000     -        0.0000    0.0000 64

 39 phi    -92.00  -28.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000   84.3933    0.0000     -        0.0000    0.0000 64

 40 phi     -2.00   62.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000   84.3933    0.0000     -        0.0000    0.0000 64

 41 phi    -32.00   32.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
  40.0000   84.3933    0.0000     -        0.0000    0.0000 64

;
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25100
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        62.24
_diffrn_reflns_theta_max         62.24
_diffrn_reflns_theta_min         4.71
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75819
_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    1.396
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.035(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^]         where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0626
_reflns_number_gt                2406
_reflns_number_total             2687
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol8002749-file003.cif
_cod_data_source_block           g172
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_database_code               1504609