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_1501812
_publ_section_title
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 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 H32 O6'
_chemical_formula_sum            'C22 H32 O6'
_chemical_formula_weight         392.48
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_cell_angle_beta                 90.176(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1972(10)
_cell_length_b                   8.9304(5)
_cell_length_c                   18.0154(14)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      67.8
_cell_measurement_theta_min      4.3
_cell_volume                     1962.3(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.980
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18784
_diffrn_reflns_theta_full        66.6
_diffrn_reflns_theta_max         68.1
_diffrn_reflns_theta_min         3.6
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.835
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.14
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details '3106 Bijvoet pairs, (Flack, 1983)'
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         6870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.3233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0747
_reflns_number_gt                6795
_reflns_number_total             6870
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            np100956k_si_002.cif
_cod_data_source_block           LS-1
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_H-M      'P 21 '
_cod_database_code               1501812