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_4029433
_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_formula_moiety         'C18 H21 N O3'
_chemical_formula_sum            'C18 H21 N O3'
_chemical_formula_weight         299.36
_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                   5.8822(3)
_cell_length_b                   15.7145(8)
_cell_length_c                   16.2267(7)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      2.51
_cell_volume                     1499.93(13)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX 2 CCD'
_diffrn_measurement_method       '\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  0.0850
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17322
_diffrn_reflns_theta_full        29.17
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.699
_exptl_crystal_size_mid          0.548
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0701P)^2^+0.1514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                3859
_reflns_number_total             3996
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo500568s_si_002.cif
_cod_data_source_block           knih91
_cod_depositor_comments
'Adding full bibliography for 4029432--4029433.cif.'
_cod_database_code               4029433