Total synthesis of norcembrenolide B and scabrolide D.
Saitman, Alec; Rulliere, Pauline; Sullivan, Steven D. E.; Theodorakis, Emmanuel A.; Organic letters 13 (2011) 5854–5857; doi:10.1021/ol202476j

data_1502560
_publ_section_title
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 Total synthesis of norcembrenolide B and scabrolide D.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5854
_journal_page_last               5857
_journal_paper_doi               10.1021/ol202476j
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C19 H24 O6'
_chemical_formula_weight         348.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.2160(10)
_cell_angle_beta                 93.2230(10)
_cell_angle_gamma                100.9200(10)
_cell_formula_units_Z            2
_cell_length_a                   5.9436(2)
_cell_length_b                   8.0046(3)
_cell_length_c                   18.5428(7)
_cell_measurement_reflns_used    6512
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.65
_cell_volume                     845.70(5)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       7
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_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12847
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.000(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.2945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                3323
_reflns_number_total             3829
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202476j_si_006.cif
_cod_data_source_block           Theod60
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502560