Captopril and its dimer captopril disulfide: comparative structural and conformational studies
Bojarska, Joanna; Maniukiewicz, Waldemar; Fruziński, Andrzej; Sieroń, Lesław; Remko, Milan; Acta Crystallographica Section C 71 (2015) –; doi:10.1107/S2053229615002582

data_2019871
_publ_section_title
;
 Captopril and its dimer captopril disulfide: comparative structural and
 conformational studies
;
_journal_coeditor_code           WQ3085
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615002582
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C18 H28 N2 O6 S2'
_chemical_formula_moiety         'C18 H28 N2 O6 S2'
_chemical_formula_sum            'C18 H28 N2 O6 S2'
_chemical_formula_weight         432.54
_chemical_name_common            'captopril disulfide'
_chemical_name_systematic
1,1'-{Disulfanediylbis[(2<i>S</i>)-2-methyl-1-oxopropane-3,1-diyl]}bis-<i>L</i>-proline
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 91.925(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6678(4)
_cell_length_b                   11.0680(6)
_cell_length_c                   14.4219(8)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.40
_cell_measurement_theta_min      3.07
_cell_volume                     1063.72(10)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2008)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>, 2008)
;
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11298
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.391
_diffrn_reflns_theta_min         3.066
_exptl_absorpt_coefficient_mu    2.585
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.246
_refine_ls_abs_structure_details
;
Flack <i>x</i> parameter determined using 1578 quotients
[(I+)-(I-)]/[(I+)+(I-)] (Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.007(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0580P)^2^+0.9380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                3626
_reflns_number_total             3675
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            wq3085sup1.cif
_cod_data_source_block           2
_cod_database_code               2019871
_cod_database_fobs_code          2019871
_shelx_estimated_absorpt_t_min   0.564
_shelx_estimated_absorpt_t_max   0.698
_shelx_hkl_checksum              52337
_shelx_res_checksum              54850