Electronic structure, novel synthesis, and O—H···O and C—H···O interactions in two 6-oxopiperidine-2-carboxylic acid derivatives
Vrábel, Viktor; Sivý, Július; Šafář, Peter; Marchalín, Štefan; Acta Crystallographica Section C 70 (2014) 817–822; doi:10.1107/S2053229614016301

data_2019638
_publ_section_title
;
 Electronic structure, novel synthesis, and O---H&#x00B7;&#x00B7;&#x00B7;O
 and C---H&#x00B7;&#x00B7;&#x00B7;O interactions in two
 6-oxopiperidine-2-carboxylic acid derivatives
;
_journal_coeditor_code           CU3059
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              817
_journal_page_last               822
_journal_paper_doi               10.1107/S2053229614016301
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H13 N O3 S'
_chemical_formula_moiety         'C11 H13 N O3 S'
_chemical_formula_sum            'C11 H13 N O3 S'
_chemical_formula_weight         239.28
_chemical_name_systematic
;
(<i>S</i>)-6-Oxo-1-(thiophen-3-ylmethyl)piperidine-2-carboxylic acid
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9560(4)
_cell_length_b                   10.3710(5)
_cell_length_c                   13.8612(6)
_cell_measurement_reflns_used    5924
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5150
_cell_measurement_theta_min      3.5250
_cell_volume                     1143.71(9)
_computing_cell_refinement       '<i>CrysAlis CCD</i> (Oxford Diffraction, 2009'
_computing_data_collection
'<i>CrysAlis CCD</i> (Oxford Diffraction, 2009)'
_computing_data_reduction
'<i>CrysAlis RED</i> (Oxford Diffraction, 2009)'
_computing_molecular_graphics
;
<i>SHELXL97</i> (Sheldrick, 2008), <i>PLATON</i> (Spek, 2009)
and <i>WinGX</i>
(Farrugia, 2012)
;
_computing_structure_refinement  '<i>SHELXS97</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 5.2170
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Oxford Xcalibur Gemini diffractometer with Ruby CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17583
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90729
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis RED (Oxford Diffraction, 2009),
based on expressions derived by Clark & Reid (1995)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.183
_refine_ls_abs_structure_details 'Flack (1983), with 867 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0393P)^2^+0.1785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                1921
_reflns_number_total             2098
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cu3059sup1.cif
_cod_data_source_block           3b
_cod_database_code               2019638
_cod_database_fobs_code          2019638