Aminolactone Chiral Modifiers for Heterogeneous Asymmetric Hydrogenation: Corrected Structure of Pantoyl-Naphthylethylamine, In-Situ Hydrogenolysis, and Scanning Tunneling Microscopy Observation of Supramolecular Aminolactone/Substrate Assemblies on Pt(111)
Goubert, Guillaume; Demers-Carpentier, Vincent; Loach, Richard P.; Lafleur-Lambert, Raphaél; Lemay, Jean-Christian; Boukouvalas, John; McBreen, Peter H.; ACS Catalysis 3 (2013) 2677–; doi:10.1021/cs4007588

data_4508605
_publ_section_title
;
 Aminolactone Chiral Modifiers for Heterogeneous Asymmetric Hydrogenation:
 Corrected Structure of Pantoyl-Naphthylethylamine, In-Situ
 Hydrogenolysis, and Scanning Tunneling Microscopy Observation of
 Supramolecular Aminolactone/Substrate Assemblies on Pt(111)
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              2677
_journal_paper_doi               10.1021/cs4007588
_journal_volume                  3
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C18 H21 N O2'
_chemical_formula_sum            'C18 H21 N O2'
_chemical_formula_weight         283.36
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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
_cell_angle_beta                 107.3713(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.65410(16)
_cell_length_b                   8.25169(6)
_cell_length_c                   17.39574(12)
_cell_measurement_reflns_used    14357
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.65
_cell_measurement_theta_min      2.66
_cell_volume                     3103.55(4)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.018
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20187
_diffrn_reflns_theta_full        70.95
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_correction_T_min  0.8735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), 2119 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.03(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0672P)^2^+0.3734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                5298
_reflns_number_total             5337
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cs4007588_si_002.cif
_cod_data_source_block           breen2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3103.55(5)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4508605