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_4030152
_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_sum            'C35 H40 O7'
_chemical_formula_weight         572.67
_space_group_IT_number           4
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.0560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6491(2)
_cell_length_b                   7.40420(10)
_cell_length_c                   16.8171(3)
_cell_measurement_reflns_used    18196
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      135.00
_cell_measurement_theta_min      5.40
_cell_volume                     1545.80(4)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Micro source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24377
_diffrn_reflns_theta_full        67.77
_diffrn_reflns_theta_max         67.77
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.7800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), XXXX Friedel Pairs'
_refine_ls_abs_structure_Flack   0.06(10)
_refine_ls_extinction_coef       0.0026(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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5122
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0335P)^2^+0.2032P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0673
_reflns_number_gt                5014
_reflns_number_total             5122
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5015195_si_003.cif
_cod_data_source_block           han444
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (45
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (62
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (80
times).

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4030152