Phosphorodiamidate-directed metalation of N-heterocycles using Mg- and Zn-TMP bases.
Rohbogner, Christoph J.; Wirth, Stefan; Knochel, Paul; Organic letters 12 (2010) 1984–1987; doi:10.1021/ol100453x

data_1502928
_publ_section_title
;
 Phosphorodiamidate-directed metalation of N-heterocycles using Mg- and
 Zn-TMP bases.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1984
_journal_page_last               1987
_journal_paper_doi               10.1021/ol100453x
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C22 H26 N3 O4 P'
_chemical_formula_sum            'C22 H26 N3 O4 P'
_chemical_formula_weight         427.433
_chemical_name_systematic
'Ethyl 3-{[bis(dimethylamino)phosphoryl]oxy}-2-phenylquinoline-4-carboxylate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.89(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.619(3)
_cell_length_b                   11.209(2)
_cell_length_c                   14.083(3)
_cell_measurement_reflns_used    8367
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.103
_cell_measurement_theta_min      3.134
_cell_volume                     2142.0(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics
;
Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_radiation_collimation    0.25
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15784
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         3.15
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.3255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method
'Slow evaporation of a solution in EtOAc/heptane at rt'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0517P)^2^+0.4109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                3249
_reflns_number_total             4700
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100453x_si_002.cif
_cod_data_source_block           12a_(CCDC_766953)
_cod_original_cell_volume        2142.0(7)
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1502928
_kl_diffrn_measurement_scan_angle phi/omega-scan
_kl_diffrn_measurement_scan_step_degree 2.0
_kl_diffrn_measurement_scan_time_per_degree 5.5
_kl_diffrn_measurement_detector_distance 30