Synthetic studies of neoclerodane diterpenes from Salvia divinorum: preparation and opioid receptor activity of salvinicin analogues.
Simpson, Denise S.; Katavic, Peter L.; Lozama, Anthony; Harding, Wayne W.; Parrish, Damon; Deschamps, Jeffrey R.; Dersch, Christina M.; Partilla, John S.; Rothman, Richard B.; Navarro, Hernan; Prisinzano, Thomas E.; Journal of medicinal chemistry 50 (2007) 3596–3603; doi:10.1021/jm070393d

data_1505031
_publ_section_title
;
 Synthetic studies of neoclerodane diterpenes from Salvia divinorum:
 preparation and opioid receptor activity of salvinicin analogues.
;
_journal_issue                   15
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              3596
_journal_page_last               3603
_journal_paper_doi               10.1021/jm070393d
_journal_volume                  50
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H32 O8'
_chemical_formula_sum            'C23 H32 O8'
_chemical_formula_weight         436.49
_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                   6.3428(7)
_cell_length_b                   10.563(2)
_cell_length_c                   31.962(6)
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    103(1)
_cell_measurement_theta_max      28.98
_cell_measurement_theta_min      2.31
_cell_volume                     2141.4(6)
_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      103(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3461
_diffrn_reflns_theta_full        29.70
_diffrn_reflns_theta_max         29.70
_diffrn_reflns_theta_min         1.27
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.575
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.418
_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   -1.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0955P)^2^+0.3062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                3230
_reflns_number_total             3461
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jm070393dsi20070403_051755.cif
_cod_data_source_block           prnz08
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1505031