Synthesis of Enantiopure 10-Nornaltrexones in the Search for Toll-like Receptor 4 Antagonists and Opioid Ligands.
Selfridge, Brandon R.; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; The Journal of organic chemistry 79 (2014) 5007–5018; doi:10.1021/jo500568s

data_4029432
_publ_section_title
;
 Synthesis of Enantiopure 10-Nornaltrexones in the Search for Toll-like
 Receptor 4 Antagonists and Opioid Ligands.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5007
_journal_page_last               5018
_journal_paper_doi               10.1021/jo500568s
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C17 H22 N O3, C8 H7 O3'
_chemical_formula_sum            'C25 H29 N O6'
_chemical_formula_weight         439.49
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4802(3)
_cell_length_b                   13.1979(5)
_cell_length_c                   25.4488(9)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.12
_cell_measurement_theta_min      2.22
_cell_volume                     2176.51(15)
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX II 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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25206
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_correction_T_min  0.9571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.463
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+0.0746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                5413
_reflns_number_total             5793
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo500568s_si_001.cif
_cod_data_source_block           knih88
_cod_depositor_comments
'Adding full bibliography for 4029432--4029433.cif.'
_cod_database_code               4029432