Labdane diterpenoids from Leonurus sibiricus.
Wu, Hankui; Fronczek, Frank R.; Ferreira, Daneel; Burandt, Jr, Charles L; Zjawiony, Jordan K.; Journal of natural products 74 (2011) 831–836; doi:10.1021/np100956k

data_1501814
_publ_section_title
;
 Labdane diterpenoids from Leonurus sibiricus.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              831
_journal_page_last               836
_journal_paper_doi               10.1021/np100956k
_journal_volume                  74
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H34 O7'
_chemical_formula_sum            'C22 H34 O7'
_chemical_formula_weight         410.49
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3687(9)
_cell_length_b                   11.7108(9)
_cell_length_c                   15.5053(11)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      67.80
_cell_measurement_theta_min      4.74
_cell_volume                     2064.3(3)
_computing_cell_refinement       'Bruker (2006) Apex-II '
_computing_data_collection       'Bruker (2006) Apex-II'
_computing_data_reduction        'Bruker (2006) Apex-II '
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22499
_diffrn_reflns_theta_full        66.6
_diffrn_reflns_theta_max         68.27
_diffrn_reflns_theta_min         4.73
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(15)
_refine_ls_extinction_coef       0.00076(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0217P)^2^+0.9772P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                3684
_reflns_number_total             3706
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            np100956k_si_004.cif
_cod_data_source_block           Jordan10
_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_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1501814