Modification of the furan ring of salvinorin A: Identification of a selective partial agonist at the kappa opioid receptor
Béguin, Cécile; Duncan, Katharine K.; Munro, Thomas A.; Ho, Douglas M.; Xu, Wei; Liu-Chen, Lee-Yuan; Carlezon, William A.; Cohen, Bruce M.; Bioorganic & Medicinal Chemistry 17 (2009) 1370–1380; doi:10.1016/j.bmc.2008.12.012

data_1561216
_publ_section_title
;
 Modification of the furan ring of salvinorin A: Identification of a
 selective partial agonist at the kappa opioid receptor
;
_journal_issue                   3
_journal_name_full               'Bioorganic & Medicinal Chemistry'
_journal_page_first              1370
_journal_page_last               1380
_journal_paper_doi               10.1016/j.bmc.2008.12.012
_journal_volume                  17
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C23 H28 O8'
_chemical_formula_moiety         'C23 H28 O8'
_chemical_formula_structural     'C23 H28 O8'
_chemical_formula_sum            'C23 H28 O8'
_chemical_formula_weight         432.45
_chemical_melting_point          490
_chemical_name_common            '12-epi-Salvinorin A'
_chemical_name_systematic
; 
(2<i>R</i>,4a<i>R</i>,6a<i>R</i>,7<i>R</i>,9<i>S</i>,10a<i>S</i>,10b<i>R</i>)-
Methyl 9-Acetoxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxododecahydro-
1<i>H</i>-benzo[<i>f</i>]isochromene-7-carboxylate
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_audit_update_record
;
2008-11-10 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.557(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0762(3)
_cell_length_b                   8.7620(2)
_cell_length_c                   11.5110(3)
_cell_measurement_reflns_used    9733
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.50
_cell_volume                     1116.03(5)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXTL v6.12 (Bruker AXS, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       '\w scans, 1840 0.5\% rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21536
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_recrystallization_method 'Evaporation from EtOAc/hexanes'
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(5)
_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     284
_refine_ls_number_reflns         6522
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0656P)^2^+0.0523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                5990
_reflns_number_total             6522
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            Beguin-supplementary.cif
_cod_data_source_block           bmc08003
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1561216
_cod_database_fobs_code          1561216