Thiolation of symmetrical and unsymmetrical diketopiperazines.
Ruff, Bettina M.; Zhong, Sabilla; Nieger, Martin; Bräse, Stefan; Organic & biomolecular chemistry 10 (2012) 935–940; doi:10.1039/c2ob06663g

data_7152211
_publ_section_title
;
 Thiolation of symmetrical and unsymmetrical diketopiperazines.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              935
_journal_page_last               940
_journal_paper_doi               10.1039/c2ob06663g
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C22 H30 N4 O4 S2, 0.125(H2 O)'
_chemical_formula_sum            'C22 H30.25 N4 O4.125 S2'
_chemical_formula_weight         480.88
_chemical_name_systematic
;
(rac)-10a,10'a-bis(methylthio)octahydro-1H,1'H-5a,5'a-bidipyrrolo-
[1,2-a:1',2'-d]pyrazine-5,5',10,10'(6H,6'H,10aH,10'aH)-tetraone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.68(1)
_cell_angle_beta                 103.17(1)
_cell_angle_gamma                91.75(1)
_cell_formula_units_Z            4
_cell_length_a                   9.648(1)
_cell_length_b                   14.822(2)
_cell_length_c                   16.441(3)
_cell_measurement_reflns_used    51
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     2204.8(6)
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0840
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15993
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1021
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         7743
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0519P)^2^+3.2612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                5119
_reflns_number_total             7743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob06663g.txt
_cod_data_source_block           sb108_hy
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               7152211