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_4037349
_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 ad
_chemical_formula_moiety         'C17 H23 Cl1 O5'
_chemical_formula_sum            'C17 H23 Cl O5'
_chemical_formula_weight         342.82
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 110.456(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6723(7)
_cell_length_b                   7.1954(4)
_cell_length_c                   11.9267(8)
_cell_measurement_reflns_used    4719
_cell_measurement_temperature    123
_cell_measurement_theta_max      69
_cell_measurement_theta_min      4
_cell_volume                     858.11(10)
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6396
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         68.888
_diffrn_reflns_theta_min         4.422
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_recrystallization_method
; 
 
;
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.21
_refine_ls_abs_structure_details 'Flack (1983), 1339 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.045(17)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.0057219
_refine_ls_shift/su_mean         0.0003348
_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: 
 0.223 0.129 0.748E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0487
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0461
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2695
_reflns_number_total             2940
_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   0.0405
_oxford_refine_ls_scale          0.2931(6)
_oxford_reflns_number_all        2928
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            jo6b02039_si_002.cif
_cod_data_source_block           57
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' 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_original_cell_volume        858.11(6)
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C17 H23 Cl1 O5'
_cod_database_code               4037349