Origin of the chemical stability of phosphine-phosphoramidites: structural study of an UPPhos-type crystal and application of UPPhos in the asymmetric hydrogenation of imines
Balogh, Szabolcs; Farkas, Gergely; Holczbauer, Tamás; Bakos, József; Acta Crystallographica Section C 73 (2017) –; doi:10.1107/S2053229617010403

data_2020832
_publ_section_title
;
 Origin of the chemical stability of phosphine-phosphoramidites:
 structural study of an UPPhos-type crystal and application of UPPhos in
 the asymmetric hydrogenation of imines
;
_journal_coeditor_code           SK3658
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229617010403
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C38 H35 N O2 P2'
_chemical_formula_moiety         'C38 H35 N O2 P2'
_chemical_formula_sum            'C38 H35 N O2 P2'
_chemical_formula_weight         599.61
_chemical_name_systematic
(11<i>bS</i>)-<i>N</i>-[(2<i>S</i>,4<i>S</i>)-4-(Diphenylphosphanyl)pentan-2-yl]-<i>N</i>-methyldinaphtho[2,1-<i>d</i>:1',2'-<i>f</i>][1,3,2]dioxaphosphepin-4-amine
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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   direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.0806(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.7931(5)
_cell_length_b                   10.4209(5)
_cell_length_c                   14.0792(6)
_cell_measurement_reflns_used    30659
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      3.10
_cell_volume                     1614.46(12)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2008
;
_computing_data_collection
;
CrystalClear (Rigaku, 2008)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2008)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            46478
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.101
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(<i>NUMABS</i>; Higashi, 2002)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.690
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.150
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1519 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5701
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0341P)^2^+0.2524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                4190
_reflns_number_total             5701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3658sup1.cif
_cod_data_source_block           I
_cod_database_code               2020832
_cod_database_fobs_code          2020832
_shelx_estimated_absorpt_t_min   0.892
_shelx_estimated_absorpt_t_max   0.950
_shelx_hkl_checksum              56278
_shelx_res_checksum              70347