Dearomatizing Anionic Cyclization of N-Alkyl-N-benzyl(dinaphthyl)phosphinamides. A Facile Route to γ-(Amino)dihydronaphthalenylphosphinic Acids
Gloria Ruiz-Gómez; María José Iglesias; Manuel Serrano-Ruiz; Fernando López-Ortiz; Journal of Organic Chemistry 72 (2007) 9704–9712; doi:10.1021/jo701607s

data_4023055
_publ_section_title
;
 Dearomatizing Anionic Cyclization of
 N-Alkyl-N-benzyl(dinaphthyl)phosphinamides. A Facile Route
 to \g-(Amino)dihydronaphthalenylphosphinic Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9704
_journal_page_last               9712
_journal_paper_doi               10.1021/jo701607s
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C28 H24 N O P'
_chemical_formula_weight         421.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.463(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.149(9)
_cell_length_b                   19.342(9)
_cell_length_c                   11.087(5)
_cell_measurement_reflns_used    623
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.160
_cell_measurement_theta_min      4.520
_cell_volume                     4515(3)
_computing_cell_refinement       'Bruker APEX'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.1016
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20848
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         0.97
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         6488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0522P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                3250
_reflns_number_total             6488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701607s-File005.cif
_cod_data_source_block           c:\sir97\fernando\r632\r632
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023055