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_4022396
_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            'C19.35 H29.7 Cl0.7 O5.5'
_chemical_formula_weight         375.16
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_audit_creation_date             2002-12-30
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                90
_cell_angle_beta                 115.6(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.920(1)
_cell_length_b                   7.3606(5)
_cell_length_c                   17.285(1)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    273.2
_cell_measurement_theta_max      0.0
_cell_measurement_theta_min      0.0
_cell_volume                     2057(2)
_computing_cell_refinement       ' 'Enraf-Nonius KAPPA CCD''
_computing_data_collection       ' 'Enraf-Nonius KAPPA CCD''
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution    'SIR 92'
_diffrn_ambient_temperature      273.2
_diffrn_measured_fraction_theta_full 0.85
_diffrn_measured_fraction_theta_max 0.85
_diffrn_measurement_device_type  'Enraf-Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      0.00000
_diffrn_orient_matrix_UB_12      0.00000
_diffrn_orient_matrix_UB_13      0.00000
_diffrn_orient_matrix_UB_21      0.00000
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      0.00000
_diffrn_orient_matrix_UB_31      0.00000
_diffrn_orient_matrix_UB_32      0.00000
_diffrn_orient_matrix_UB_33      0.00000
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.06689
_diffrn_reflns_av_sigmaI/netI    0.070
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11521
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             806.80
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.977
_refine_ls_goodness_of_fit_ref   1.977
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     233
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0875
_refine_ls_shift/su_max          0.0063
_refine_ls_shift/su_mean         0.8220
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00148|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.1156
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                1988
_reflns_number_total             2915
_reflns_threshold_expression     I>1.20\s(I)
_cod_data_source_file            jo0340049si20030213_095327_5.cif
_cod_data_source_block           C19O5H28.(H2O)0.5.(CH2Cl2)0.35
_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

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      'C 2        '
_cod_original_formula_sum        'C19.35 H29.70 Cl0.70 O5.50 '
_cod_database_code               4022396