Chiral pyridyl phosphinites with large aryl substituents as efficient ligands for the asymmetric iridium-catalyzed hydrogenation of difficult substrates
Woodmansee, David H.; Müller, Marc-André; Neuburger, Marcus; Pfaltz, Andreas; Chemical Science 1 (2010) 72–; doi:10.1039/c0sc00223b

data_1515871
_publ_section_title
;
 Chiral pyridyl phosphinites with large aryl substituents as efficient
 ligands for the asymmetric iridium-catalyzed hydrogenation of difficult
 substrates
;
_journal_issue                   1
_journal_name_full               'Chemical Science'
_journal_page_first              72
_journal_paper_doi               10.1039/c0sc00223b
_journal_volume                  1
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H19 N1 O1'
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.41
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                106.2280(10)
_cell_angle_beta                 98.815(2)
_cell_angle_gamma                101.2650(10)
_cell_formula_units_Z            4
_cell_length_a                   7.6503(2)
_cell_length_b                   12.8616(4)
_cell_length_c                   18.8654(6)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    123
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     1704.86(9)
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36112
_diffrn_reflns_theta_full        29.305
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_min         1.704
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     901
_refine_ls_number_reflns         9563
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001180
_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:
0.193 0.168 0.451E-01
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0636
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0472
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              17
_reflns_limit_k_min              -18
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                9563
_reflns_number_total             10342
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.40
_oxford_diffrn_Wilson_scale      26.09
_oxford_refine_ls_r_factor_ref   0.0408
_oxford_refine_ls_scale          0.2081(2)
_oxford_reflns_number_all        10318
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            c0sc00223b.txt
_cod_data_source_block           12g
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_formula_sum        'C23 H19 N1 O1'
_cod_database_code               1515871