Studies toward bivalent κ opioids derived from salvinorin A: heteromethylation of the furan ring reduces affinity.
Munro, Thomas A.; Xu, Wei; Ho, Douglas M.; Liu-Chen, Lee-Yuan; Cohen, Bruce M.; Beilstein journal of organic chemistry 9 (2013) 2916–2924; doi:10.3762/bjoc.9.328

data_4029696
_publ_section_title
;
 Studies toward bivalent \k opioids derived from salvinorin A:
 heteromethylation of the furan ring reduces affinity.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              2916
_journal_page_last               2924
_journal_paper_doi               10.3762/bjoc.9.328
_journal_volume                  9
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_compound_source        'chemical synthesis'
_chemical_formula_iupac          'C26 H35 N O8 . 0.25(C2 H6 O)'
_chemical_formula_moiety         'C26 H35 N O8, 0.25(C2 H6 O)'
_chemical_formula_structural     '(C26 H35 N O8) 0.25(C2 H6 O)'
_chemical_formula_sum            'C26.5 H36.5 N O8.25'
_chemical_formula_weight         501.07
_chemical_melting_point_gt       429
_chemical_melting_point_lt       431
_chemical_name_common            '16-(Dimethylaminomethyl)salvinorin A'
_chemical_name_systematic
;
(2<i>S</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-[2-(dimethylaminomethyl)-3-furyl]-6a,10b-dimethyl-
4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1<i>H</i>-benzo[<i>f</i>]isochromene-
7-carboxylate
;
_space_group_IT_number           4
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 109.839(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.9397(2)
_cell_length_b                   10.1557(2)
_cell_length_c                   12.7466(2)
_cell_measurement_reflns_used    5859
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.86
_cell_measurement_theta_min      2.63
_cell_volume                     1332.10(4)
_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 v2008/4 (Bruker AXS, 2008)'
_computing_publication_material  'SHELXTL v2008/4 (Bruker AXS, 2008)'
_computing_structure_refinement  'SHELXTL v2008/4 (Bruker AXS, 2008)'
_computing_structure_solution    'SHELXTL v2008/4 (Bruker AXS, 2008)'
_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, 1228 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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17282
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             537
_exptl_crystal_recrystallization_method
;
dissolved in minimal hot ethanol, diluted to approximately 10% in 
hexanes, warmed until clear, then left to evaporate in a fumehood.
;
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.990
_refine_diff_density_min         -0.354
_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   -0.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         7755
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0584
_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^)+(0.1211P)^2^+0.0446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1820
_reflns_number_gt                6232
_reflns_number_total             7755
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            1860-5397-9-328-S3.cif
_cod_data_source_block           bmc08002
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C26.50 H36.50 N O8.25'
_cod_database_code               4029696
_cod_database_fobs_code          4029696