Synthesis of Pyridyl-dihydrobenzooxaphosphole Ligands and Their Application in Asymmetric Hydrogenation of Unfunctionalized Alkenes.
Qu, Bo; Samankumara, Lalith P.; Savoie, Jolaine; Fandrick, Daniel R.; Haddad, Nizar; Wei, Xudong; Ma, Shengli; Lee, Heewon; Rodriguez, Sonia; Busacca, Carl A.; Yee, Nathan K.; Song, Jinhua J.; Senanayake, Chris H.; The Journal of organic chemistry 79 (2014) 993–; doi:10.1021/jo4024864

data_4029010
_publ_section_title
;
 Synthesis of Pyridyl-dihydrobenzooxaphosphole Ligands and Their
 Application in Asymmetric Hydrogenation of Unfunctionalized Alkenes.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              993
_journal_paper_doi               10.1021/jo4024864
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H20 N O3 P'
_chemical_formula_sum            'C17 H20 N O3 P'
_chemical_formula_weight         317.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2013-07-30
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8869(5)
_cell_length_b                   9.9389(6)
_cell_length_c                   16.1785(9)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_max      66.54
_cell_measurement_theta_min      5.22
_cell_volume                     1589.78(15)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9919
_diffrn_measured_fraction_theta_max 0.9919
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12398
_diffrn_reflns_theta_full        66.5746
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_min         2.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.637
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7106
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1482 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.7106.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3257
_exptl_crystal_description       Plate
_exptl_crystal_F_000             675.1954
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.2087
_refine_diff_density_min         -0.2389
_refine_diff_density_rms         0.0536
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.023(13)
_refine_ls_d_res_high            0.8401
_refine_ls_d_res_low             8.4685
_refine_ls_goodness_of_fit_ref   1.0439
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0439
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.2253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0689
_reflns_Friedel_coverage         0.986
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                2778
_reflns_number_total             2801
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo4024864_si_001.cif
_cod_data_source_block           scan_0m_P212121
_cod_database_code               4029010
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
;