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_2311612
_publ_section_title
;
 Preparation and structural analysis of (+-)-threo-ritalinic acid.
;
_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_moiety         'Cl, C14 H20 N O2'
_chemical_formula_sum            'C14 H20 Cl N O2'
_chemical_formula_weight         269.76
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-17
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.781(4)
_cell_length_b                   9.1981(13)
_cell_length_c                   7.3785(16)
_cell_measurement_reflns_used    714
_cell_measurement_temperature    100
_cell_measurement_theta_max      18.325
_cell_measurement_theta_min      3.385
_cell_volume                     1410.4(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Nonius APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1649
_diffrn_reflns_av_unetI/netI     0.1684
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16807
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.572
_diffrn_reflns_theta_min         1.960
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method CH3OH
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details
;
 Flack x determined using 368 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.2314
_refine_ls_R_factor_gt           0.0903
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1500P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2205
_refine_ls_wR_factor_ref         0.3017
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                1229
_reflns_number_total             2850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            fm3004sup5.cif
_cod_data_source_block           x231012_0ma
_cod_database_code               2311612
_shelx_hkl_checksum              51499
_shelx_res_checksum              3563
_shelxl_version_number           2013-4