Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development.
Shaw, Scott A.; Balasubramanian, Balu; Bonacorsi, Samuel; Cortes, Janet Caceres; Cao, Kevin; Chen, Bang-Chi; Dai, Jun; Decicco, Carl; Goswami, Animesh; Guo, Zhiwei; Hanson, Ronald; Humphreys, W. Griffith; Lam, Patrick Y. S.; Li, Wenying; Mathur, Arvind; Maxwell, Brad D.; Michaudel, Quentin; Peng, Li; Pudzianowski, Andrew; Qiu, Feng; Su, Shun; Sun, Dawn; Tymiak, Adrienne A.; Vokits, Benjamin P.; Wang, Bei; Wexler, Ruth; Wu, Dauh-Rurng; Zhang, Yingru; Zhao, Rulin; Baran, Phil S.; The Journal of organic chemistry 80 (2015) 7019–7032; doi:10.1021/acs.joc.5b00632

data_4031168
_publ_section_title
;
 Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel:
 Determination of Structure and Analyte Development.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7019
_journal_page_last               7032
_journal_paper_doi               10.1021/acs.joc.5b00632
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H16 Cl N O3 S'
_chemical_formula_weight         337.81
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.591(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6560(11)
_cell_length_b                   15.213(3)
_cell_length_c                   8.0795(14)
_cell_measurement_reflns_used    1176
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      59.98
_cell_measurement_theta_min      2.90
_cell_volume                     798.4(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  KappaCCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2282
_diffrn_reflns_theta_full        59.98
_diffrn_reflns_theta_max         59.98
_diffrn_reflns_theta_min         5.61
_exptl_absorpt_coefficient_mu    3.443
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2282
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0453P)^2^+0.2941P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                2260
_reflns_number_total             2282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00632_si_002.cif
_cod_data_source_block           82583-018a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031167--4031168.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               4031168