Conception and Evolution of Stereocontrolled Strategies toward Functionalized 8-Aryloctanoic Acids Related to the Total Synthesis of Aliskiren.
Hanessian, Stephen; Chénard, Etienne; Guesné, Sébastien; Cusson, Jean-Philippe; The Journal of organic chemistry 79 (2014) 9531–9545; doi:10.1021/jo5015195

data_4029999
_publ_section_title
;
 Conception and Evolution of Stereocontrolled Strategies toward
 Functionalized 8-Aryloctanoic Acids Related to the Total Synthesis of
 Aliskiren.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9531
_journal_page_last               9545
_journal_paper_doi               10.1021/jo5015195
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C21 H32 O5'
_chemical_formula_sum            'C21 H32 O5'
_chemical_formula_weight         364.47
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   25.5016(5)
_cell_length_b                   25.5016(5)
_cell_length_c                   5.8826(1)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.57
_cell_measurement_theta_min      3.47
_cell_volume                     3313.10(11)
_computing_cell_refinement       'SAINT V7.60A(Bruker AXS, 2008)'
_computing_data_collection       'APEX2  (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT V7.60A(Bruker AXS, 2008)'
_computing_molecular_graphics    'SHELXTL  (Bruker AXS, 2003)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Quazar MX'
_diffrn_radiation_source         'Incoatec I\muS Microsource '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            44115
_diffrn_reflns_theta_full        71.18
_diffrn_reflns_theta_max         71.18
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.8428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_platon_squeeze_details
;
The crystal structure has been squeezed out with PLATON to remove highly
disordered ether or hexane contributions from its solvate structure. Hexanes
and ether (9:1) were used as the recrystallization solvent. PLATON found a 
263.1 A^3 solvent accessible void volume with a contribution of 66 
electrons per cell. 
Given the presence of the highly disordered solvent in the unit cell, the 
"unsqueezed" unit cell formula will contain additional atoms, corresponding 
to the identity of the solvent. This will also increase the density and F000
of the "unsqueezed" unit cell.  
;
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
'Flack, H.D., Schwarzenbach, D.(1999),  4181 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.09(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     782
_refine_ls_number_reflns         8463
_refine_ls_number_restraints     583
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0966P)^2^+0.1237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                7719
_reflns_number_total             8463
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5015195_si_004.cif
_cod_data_source_block           robe17
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4029998--4030001.cif.
;
_cod_original_sg_symbol_H-M      P32
_cod_database_code               4029999