One-pot tandem 1,4-1,2-addition of phosphites to quinolines.
De Blieck, Ann; Masschelein, Kurt G R; Dhaene, Fréderic; Rozycka-Sokolowska, Ewa; Marciniak, Bernard; Drabowicz, Jozef; Stevens, Christian V; Chemical communications (Cambridge, England) 46 (2009) 258–260; doi:10.1039/b906808b

data_7105136
_publ_section_title
;
 One-pot tandem 1,4-1,2-addition of phosphites to quinolines.
;
_journal_issue                   2
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              258
_journal_page_last               260
_journal_paper_doi               10.1039/b906808b
_journal_volume                  46
_journal_year                    2009
_chemical_formula_moiety         'C13 H20 N2 O8 P2'
_chemical_formula_sum            'C13 H20 N2 O8 P2'
_chemical_formula_weight         394.25
_chemical_name_common
2,6-Bis(dimethoxyphosphoryl)-1,2,3,4-tetrahydroquinoline
_chemical_name_systematic
;
2,6-Bis(dimethoxyphosphoryl)-1,2,3,4-tetrahydroquinoline
;
_space_group_IT_number           2
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                63.537(4)
_cell_angle_beta                 80.792(3)
_cell_angle_gamma                67.351(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0124(4)
_cell_length_b                   10.3614(5)
_cell_length_c                   10.4335(4)
_cell_measurement_reflns_used    19124
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.18
_cell_volume                     894.17(7)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur3\\^TM\\^ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19124
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.98000
_exptl_absorpt_correction_T_min  0.96596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.0536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1463
_reflns_number_gt                2307
_reflns_number_total             3389
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b906808b.txt
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7105136