Preparation and structural analysis of (±)-threo-ritalinic acid.
Wyss, Sara; Werner, Irmgard A.; Schweizer, W. Bernd; Ametamey, Simon M.; Milicevic Sephton, Selena; Acta crystallographica. Section C, Crystal structure communications 69 (2013) 1225–1228; doi:10.1107/S010827011302595X

data_2311613
_publ_section_title
;
 Preparation and structural analysis of (+-)-threo-ritalinic acid.
;
_journal_coeditor_code           FM3004
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section C, Crystal structure communications'
_journal_page_first              1225
_journal_page_last               1228
_journal_paper_doi               10.1107/S010827011302595X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C13 H17 N O2'
_chemical_formula_moiety         'C13 H17 N O2'
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.28
_chemical_name_common            '(+-)-<i>threo</i>-Ritalinic acid'
_chemical_name_systematic
;
(<i>R</i>,<i>R</i>)-2-Phenyl-2-(piperidin-2-yl)acetic acid
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.368(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.495(3)
_cell_length_b                   5.6335(12)
_cell_length_c                   15.721(4)
_cell_measurement_reflns_used    895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.28
_cell_measurement_theta_min      3.20
_cell_volume                     1127.5(5)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and ORTEPIII (Johnson & Burnett, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement
'OLEX2 (Dolomanov <i>et al.</i>, 2009) and SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0969
_diffrn_reflns_av_sigmaI/netI    0.1068
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10280
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.1328
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                1482
_reflns_number_total             2603
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fm3004sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1127.5(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2311613
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.998
_shelx_hkl_checksum              32712
_shelx_res_checksum              53576
_shelxl_version_number           .2013