Total Synthesis of the Labdane Diterpenes Galanal A and B from Geraniol.
Lin, Shih-Che; Chein, Rong-Jie; The Journal of organic chemistry 82 (2017) 1575–1583; doi:10.1021/acs.joc.6b02766

data_4032132
_publ_section_title
;
 Total Synthesis of the Labdane Diterpenes Galanal A and B from Geraniol.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1575
_journal_page_last               1583
_journal_paper_doi               10.1021/acs.joc.6b02766
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C18 H29 N O'
_chemical_formula_sum            'C18 H29 N O'
_chemical_formula_weight         275.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 102.9530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2235(3)
_cell_length_b                   7.1760(2)
_cell_length_c                   21.8858(7)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.46
_cell_volume                     1564.77(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34645
_diffrn_reflns_point_group_measured_fraction_full 1
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_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.235
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.9099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                2817
_reflns_number_total             3192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02766_si_002.cif
_cod_data_source_block           i15011
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4032132--4032133.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4032132
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.993