Solution- and Solid-State Conformations of C(α)-Alkyl Analogues of Methylphenidate (Ritalin) Salts: Avoidance of gauche+gauche- Interactions
Avital Steinberg; Mark Froimowitz; Damon A. Parrish; Jeffrey R. Deschamps; Robert Glaser; Journal of Organic Chemistry 76 (2011) 9239–9245; doi:10.1021/jo201415h

data_4026733
_publ_contact_author_address
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;
_publ_contact_author_email       deschamps@nrl.navy.mil
_publ_contact_author_fax         202-767-6874
_publ_contact_author_name        'Dr Jeffrey R. Deschamps'
_publ_contact_author_phone       202-767-0656
_publ_section_title
;
 Solution- and Solid-State Conformations of C(\a)-Alkyl Analogues of
 Methylphenidate (Ritalin) Salts: Avoidance of gauche+gauche- Interactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9239
_journal_page_last               9245
_journal_paper_doi               10.1021/jo201415h
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C16 H25 Cl N, Cl'
_chemical_formula_sum            'C16 H25 Cl2 N'
_chemical_formula_weight         302.27
_chemical_name_systematic
; 
 (RS,SR)-2-(1-(3-chlorophenyl)-3-methylbutyl)piperidinium chloride 
;
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'from SHELXL97 CIF, local template and enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 115.512(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8496(15)
_cell_length_b                   26.389(5)
_cell_length_c                   8.7973(15)
_cell_measurement_reflns_used    1274
_cell_measurement_temperature    93(1)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      3.09
_cell_volume                     1644.6(5)
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001b)'
_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001b)'
_computing_data_reduction
;
Bruker SAINT v6.45 (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001a)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_diffrn_ambient_temperature      93(1)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13271
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  variable
_diffrn_standards_number         698
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000b)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0665P)^2^+0.5446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                2973
_reflns_number_total             3911
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo201415h_si_003.cif
_cod_data_source_block           mark178
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               4026733