Synthesis and pharmacological effects of the enantiomers of the N-phenethyl analogues of the ortho and para e- and f-oxide-bridged phenylmorphans
Zezula, Josef; Singer, Lisa; Przybył, Anna K.; Hashimoto, Akihiro; Dersch, Christina M.; Rothman, Richard B.; Deschamps, Jeffrey; Lee, Yong Sok; Jacobson, Arthur E.; Rice, Kenner C.; Organic & Biomolecular Chemistry 6 (2008) 2868–2883; doi:10.1039/b803433h

data_7150926
_publ_section_title
;
 Synthesis and pharmacological effects of the enantiomers of the
 N-phenethyl analogues of the ortho and para e- and f-oxide-bridged
 phenylmorphans
;
_journal_issue                   16
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2868
_journal_page_last               2883
_journal_paper_doi               10.1039/b803433h
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H19 N2 O3, C10 H14 Br O4 S'
_chemical_formula_sum            'C25 H33 Br N2 O7 S'
_chemical_formula_weight         585.50
_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                   7.719(3)
_cell_length_b                   13.922(5)
_cell_length_c                   24.899(12)
_cell_measurement_reflns_used    2099
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.76
_cell_volume                     2675.7(19)
_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      93(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       '\f and \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  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18485
_diffrn_reflns_theta_full        28.51
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  variable
_diffrn_standards_number         1476
_exptl_absorpt_coefficient_mu    1.660
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000b)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.090(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.122
_refine_ls_shift/su_mean         0.024
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                5322
_reflns_number_total             6212
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b803433h.txt
_cod_data_source_block           knih34
_cod_original_cell_volume        2675.7(18)
_cod_database_code               7150926