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_1515868
_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 ad
_chemical_formula_moiety
'C34 H50 Ir N O P, C32 H12 B F24, 0.4(C6 H14), 0.55(C H2 Cl2)'
_chemical_formula_sum            'C68.95 H68.7 B Cl1.1 F24 Ir N O P'
_chemical_formula_weight         1656.36
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5137(6)
_cell_length_b                   19.4816(9)
_cell_length_c                   27.1434(11)
_cell_measurement_reflns_used    9458
_cell_measurement_temperature    123
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     7146.0(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.031
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            121195
_diffrn_reflns_theta_full        30.507
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         1.683
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.037
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3316.402
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.75
_refine_diff_density_min         -1.51
_refine_ls_abs_structure_details 'Flack (1983), 9744 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.003(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1252
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     993
_refine_ls_number_reflns         18688
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.021993
_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:
0.195 0.148 0.873E-01
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0343
_refine_ls_wR_factor_gt          0.0285
_refine_ls_wR_factor_ref         0.0279
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              38
_reflns_limit_l_min              0
_reflns_number_gt                19266
_reflns_number_total             21519
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.58
_oxford_diffrn_Wilson_scale      284.90
_oxford_refine_ls_r_factor_ref   0.0255
_oxford_refine_ls_scale          0.06281(3)
_oxford_reflns_number_all        21473
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            c0sc00223b.txt
_cod_data_source_block           7e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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        'C68.95 H68.70 B1 Cl1.10 F24 Ir1 N1 O1 P1'
_cod_database_code               1515868