Determination of the absolute configuration of ({-})-abietic acid <i>via</i> its (4<i>R</i>,5<i>R</i>,9<i>R</i>,10<i>R</i>)-7,13-abietadien-18-yl <i>p</i>-bromobenzoate derivative
González, Miguel A.; Gil-Gimeno, Maria J.; Blake, Alexander J.; Acta Crystallographica Section E 62 (2006) o3346–o3347; doi:10.1107/S1600536806026705

data_2209767
_publ_section_title
;
 Determination of the absolute configuration of ({-})-abietic acid
 <i>via</i> its
 (4<i>R</i>,5<i>R</i>,9<i>R</i>,10<i>R</i>)-7,13-abietadien-18-yl
 <i>p</i>-bromobenzoate derivative
;
_journal_coeditor_code           BT2137
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3346
_journal_page_last               o3347
_journal_paper_doi               10.1107/S1600536806026705
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C27 H35 Br O2'
_chemical_formula_moiety         'C27 H35 Br O2'
_chemical_formula_sum            'C27 H35 Br O2'
_chemical_formula_weight         471.46
_chemical_name_systematic
;
(4R,5R,9R,10R)-7,13-abietadien-18-yl p-bromobenzoate
;
_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
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.850(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4486(13)
_cell_length_b                   6.0103(9)
_cell_length_c                   20.616(3)
_cell_measurement_reflns_used    5191
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_cell_volume                     1159.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT and SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    'MERCURY (Macrae <i>et al.</i>, 2006)'
_computing_publication_material
'enCIFer (Allen <i>et al.</i>,  2004) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_av_sigmaI/netI    0.024
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10620
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.793
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             496
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 2312 Friedel pairs'
_refine_ls_abs_structure_Flack   0.000(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5228
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0317
_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^)+(0.06P)^2^+0.099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                4748
_reflns_number_total             5227
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            bt2137.cif
_cod_data_source_block           3
_cod_original_cell_volume        1159.8(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2209767
_cod_database_fobs_code          2209767