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_4026731
_publ_contact_author_address
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;
_publ_contact_author_email       dparrish@nrl.navy.mil
_publ_contact_author_fax         202-767-6874
_publ_contact_author_name        'Dr Damon A. Parrish'
_publ_contact_author_phone       202-404-2141
_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 +1), (Cl -1)'
_chemical_formula_sum            'C16 H25 Cl2 N'
_chemical_formula_weight         302.27
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-04-09
_audit_creation_method           'from SHELXL97 CIF, local template and enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 120.174(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.907(10)
_cell_length_b                   7.097(2)
_cell_length_c                   19.340(6)
_cell_measurement_temperature    93(2)
_cell_volume                     3430.1(19)
_computing_cell_refinement       'Bruker SMART v5.625 (Bruker, 2001)'
_computing_data_collection       'Bruker SMART v5.625 (Bruker, 2001)'
_computing_data_reduction
;
Bruker SAINT v6.36A (Bruker, 2002), Bruker XPREP v6.12 (Bruker, 2001)
;
_computing_molecular_graphics    'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_publication_material  'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1999)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'Bruker SMART 1000 CCD'
_diffrn_measurement_method       '\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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12088
_diffrn_reflns_theta_full        28.23
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03 (Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0684P)^2^+1.5810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1340
_reflns_number_gt                2914
_reflns_number_total             4082
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo201415h_si_001.cif
_cod_data_source_block           mark121
_cod_original_cell_volume        3430.3(19)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4026731