Stereoselective Rh-Catalyzed Hydrogenative Desymmetrization of Achiral Substituted 1,4-Dienes.
Fernández-Pérez, Héctor; Lao, Joan R.; Vidal-Ferran, Anton; Organic letters 18 (2016) 2836–2839; doi:10.1021/acs.orglett.6b01088

data_1543359
_publ_section_title
;
 Stereoselective Rh-Catalyzed Hydrogenative Desymmetrization of Achiral
 Substituted 1,4-Dienes.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2836
_journal_page_last               2839
_journal_paper_doi               10.1021/acs.orglett.6b01088
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H25 N O2'
_chemical_formula_weight         311.41
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_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   mixed
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_cell_angle_alpha                90
_cell_angle_beta                 96.069(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3889(11)
_cell_length_b                   11.6277(14)
_cell_length_c                   16.0269(18)
_cell_measurement_reflns_used    3984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.27
_cell_measurement_theta_min      2.17
_cell_volume                     1739.9(4)
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_av_unetI/netI     0.0921
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21143
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.152
_diffrn_reflns_theta_min         1.278
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 1647 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6896
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0903
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1797P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2405
_refine_ls_wR_factor_ref         0.2703
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4734
_reflns_number_total             6896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01088_si_002.cif
_cod_data_source_block           mo_JL260b_0m
_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/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1543359.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1543359
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              12180
_shelx_hkl_checksum              46355