Highly Stereocontrolled Synthesis of Natural Barbacenic Acid, Novel Bisnorditerpene from Barbacenia flava
Amaury Patin; Alice Kanazawa; Christian Philouze; Andrew E. Greene; Estela Muri; Eliezer Barreiro; Paulo C. C. Costa; Journal of Organic Chemistry 68 (2003) 3831–3837; doi:10.1021/jo0340049

data_4022392
_publ_section_title
;
 Highly Stereocontrolled Synthesis of Natural Barbacenic Acid,
 Novel Bisnorditerpene from Barbacenia flava
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3831
_journal_page_last               3837
_journal_paper_doi               10.1021/jo0340049
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C20 H34 O4'
_chemical_formula_weight         338.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2002-11-12
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                108.14(2)
_cell_angle_beta                 90.11(3)
_cell_angle_gamma                116.72(3)
_cell_formula_units_Z            4
_cell_length_a                   7.073(6)
_cell_length_b                   15.128(4)
_cell_length_c                   20.629(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      22.0
_cell_volume                     1847(2)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_diffrn_ambient_temperature      293.0
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  CAD-4
_diffrn_measurement_method       \w
_diffrn_orient_matrix_UB_11      -0.02910
_diffrn_orient_matrix_UB_12      -0.06055
_diffrn_orient_matrix_UB_13      -0.04324
_diffrn_orient_matrix_UB_21      0.02937
_diffrn_orient_matrix_UB_22      0.04712
_diffrn_orient_matrix_UB_23      -0.02765
_diffrn_orient_matrix_UB_31      0.15513
_diffrn_orient_matrix_UB_32      0.01850
_diffrn_orient_matrix_UB_33      0.00618
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7728
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        70.33
_diffrn_reflns_theta_max         70.33
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        19.09
_diffrn_standards_interval_count 120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             744.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.997
_refine_ls_goodness_of_fit_ref   1.997
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.0070
_refine_ls_shift/su_mean         0.0020
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00240|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.1078
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                5531
_reflns_number_total             7344
_reflns_threshold_expression     I>1.10\s(I)
_cod_data_source_file            jo0340049si20030213_095327_1.cif
_cod_data_source_block           C20O4H34
_cod_depositor_comments
;
 Adding the '_geom_hbond_atom_site_label_A' data item. Values of the
 data item were determined from the geometry of the molecule.

 Antanas Vaitkus,
 2017-03-06

 Changing the values of the '_atom_site_label' and '_atom_site_aniso_label'
 to match those of related data items (e. g. '_geom_angle_atom_site_label').

 Antanas Vaitkus,
 2017-03-03

The following automatic conversions were performed:
data name '_geom_bond_atom_site_label_D' replaced with
'_geom_hbond_atom_site_label_D' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_atom_site_label_H' replaced with
'_geom_hbond_atom_site_label_H' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_distance_DH' replaced with '_geom_hbond_distance_DH'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_HA' replaced with
'_geom_hbond_distance_HA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_DA' replaced with
'_geom_hbond_distance_DA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_angle_DHA' replaced with '_geom_hbond_angle_DHA' as
specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_site_symmetry_A' replaced with
'_geom_hbond_site_symmetry_A' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_original_sg_symbol_H-M      'P -1       '
_cod_original_formula_sum        'C20 H34 O4 '
_cod_database_code               4022392