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_1502927
_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         'C16 H19 F3 N3 O5 P S'
_chemical_formula_sum            'C16 H19 F3 N3 O5 P S'
_chemical_formula_weight         453.374
_chemical_name_systematic
;
4-(3-{[bis(dimethylamino)phosphoryl]oxy}pyridin-4-yl)
phenyl trifluoromethanesulfonate
;
_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'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.197(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2499(4)
_cell_length_b                   10.0927(4)
_cell_length_c                   19.7258(8)
_cell_measurement_reflns_used    3480
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.2488
_cell_measurement_theta_min      4.2442
_cell_volume                     2019.77(14)
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_molecular_graphics
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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      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Oxford Diffraction XCalibur'
_diffrn_measurement_device_type  'Sapphire CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.5 mm collimator'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8084
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         4.26
_diffrn_source                   'fine-focus sealed tube'
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_diffrn_source_power             2.00
_diffrn_source_type              'Enhance (Mo) X-ray Source'
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_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.92200
_exptl_absorpt_correction_T_min  0.90136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.49097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_recrystallization_method
'Slow evaporation of a solution in EtOAc/heptane at rt'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0482P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                2755
_reflns_number_total             4075
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100453x_si_002.cif
_cod_data_source_block           6b_(CCDC_766952)
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1502927
_kl_diffrn_measurement_detector_distance 50