Formal Total Synthesis of (-)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes.
Gomes, José; Daeppen, Christophe; Liffert, Raphael; Roesslein, Joel; Kaufmann, Elias; Heikinheimo, Annakaisa; Neuburger, Markus; Gademann, Karl; The Journal of organic chemistry 81 (2016) 11017–11034; doi:10.1021/acs.joc.6b02039

data_4037343
_publ_section_title
;
 Formal Total Synthesis of (-)-Jiadifenolide and Synthetic Studies toward
 seco-Prezizaane-Type Sesquiterpenes.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11017
_journal_page_last               11034
_journal_paper_doi               10.1021/acs.joc.6b02039
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H16 O5'
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.28
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7488(2)
_cell_length_b                   11.5545(3)
_cell_length_c                   13.9686(4)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    173
_cell_measurement_theta_max      35
_cell_measurement_theta_min      3
_cell_volume                     1250.66(6)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40767
_diffrn_reflns_theta_full        35.631
_diffrn_reflns_theta_max         35.631
_diffrn_reflns_theta_min         2.287
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0627
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.0005252
_refine_ls_shift/su_mean         0.0000656
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.207 0.197 0.739E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0469
_refine_ls_wR_factor_gt          0.0350
_refine_ls_wR_factor_ref         0.0336
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2915
_reflns_number_total             3247
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0292
_oxford_refine_ls_scale          0.3404(5)
_oxford_reflns_number_all        3241
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            jo6b02039_si_002.cif
_cod_data_source_block           14
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Direct' was changed
to 'direct' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4037343
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) H   (  13,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE O   (   4,X'S) H   (   1,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;