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_2019870
_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          'C9 H15 N O3 S'
_chemical_formula_moiety         'C9 H15 N O3 S'
_chemical_formula_sum            'C9 H15 N O3 S'
_chemical_formula_weight         217.28
_chemical_name_common
;
captopril
;
_chemical_name_systematic
'(2<i>S</i>)-1-[(2<i>S</i>)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.80010(10)
_cell_length_b                   8.8015(2)
_cell_length_c                   17.4805(3)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.36
_cell_measurement_theta_min      5.02
_cell_volume                     1046.23(3)
_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 0.999
_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  0.0209
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.980
_diffrn_reflns_theta_min         5.060
_exptl_absorpt_coefficient_mu    2.628
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.161
_refine_ls_abs_structure_details
;
Flack x parameter determined using 772 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.072(5)
_refine_ls_extinction_coef       0.0066(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         1946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0195
_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^)+(0.0256P)^2^+0.2370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0520
_reflns_number_gt                1944
_reflns_number_total             1946
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            wq3085sup1.cif
_cod_data_source_block           1
_cod_database_code               2019870
_cod_database_fobs_code          2019870
_shelx_hkl_checksum              35960
_shelx_res_checksum              20909