Design, Synthesis, and Biological Evaluation of Structurally Rigid Analogues of 4-(3-Hydroxyphenyl)piperidine Opioid Receptor Antagonists.
Runyon, Scott P.; Kormos, Chad M.; Gichinga, Moses G.; Mascarella, S. Wayne; Navarro, Hernán A; Deschamps, Jeffrey R.; Imler, Gregory H.; Carroll, F. Ivy; The Journal of organic chemistry 81 (2016) 10383–10391; doi:10.1021/acs.joc.6b01366

data_4037052
_publ_section_title
;
 Design, Synthesis, and Biological Evaluation of Structurally Rigid
 Analogues of 4-(3-Hydroxyphenyl)piperidine Opioid Receptor Antagonists.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10383
_journal_page_last               10391
_journal_paper_doi               10.1021/acs.joc.6b01366
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C12 H15 N O'
_chemical_formula_sum            'C12 H15 N O'
_chemical_formula_weight         189.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.693(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9239(3)
_cell_length_b                   16.0550(7)
_cell_length_c                   8.1077(4)
_cell_measurement_reflns_used    1164
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.77
_cell_measurement_theta_min      5.51
_cell_volume                     1013.54(8)
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.893
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.893
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_number            1643
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.706
_diffrn_reflns_theta_min         5.511
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.752989
_exptl_absorpt_correction_T_min  0.604608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       rod
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0778
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1203P)^2^+2.7420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2475
_refine_ls_wR_factor_ref         0.2697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1322
_reflns_number_total             1643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01366_si_003.cif
_cod_data_source_block           rti147
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037052
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              80443
_shelx_hkl_checksum              76529