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_4022394
_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_moiety         'C21 H34 O3 '
_chemical_formula_sum            'C21 H34 O3'
_chemical_formula_weight         334.50
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2002-12-30
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.319(3)
_cell_length_b                   12.142(6)
_cell_length_c                   14.861(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    273.2
_cell_measurement_theta_max      12.70
_cell_measurement_theta_min      11.02
_cell_volume                     1862(1)
_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)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      273.2
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  CAD-4
_diffrn_measurement_method       \w--2\q
_diffrn_orient_matrix_UB_11      -0.08897
_diffrn_orient_matrix_UB_12      -0.03234
_diffrn_orient_matrix_UB_13      0.00378
_diffrn_orient_matrix_UB_21      0.02856
_diffrn_orient_matrix_UB_22      -0.04778
_diffrn_orient_matrix_UB_23      0.05110
_diffrn_orient_matrix_UB_31      -0.02569
_diffrn_orient_matrix_UB_32      0.05886
_diffrn_orient_matrix_UB_33      0.04363
_diffrn_radiation_detector       'scintillation counter'
_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  0.06374
_diffrn_reflns_av_sigmaI/netI    0.050
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5846
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        29.96
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        5.50
_diffrn_standards_interval_count 0
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.611
_refine_ls_goodness_of_fit_ref   1.611
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.0031
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00021|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0560
_refine_ls_wR_factor_ref         0.0560
_reflns_number_gt                2260
_reflns_number_total             3716
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            jo0340049si20030213_095327_3.cif
_cod_data_source_block           C21O3H34
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C21 H34 O3 '
_cod_database_code               4022394