Dearomatizing anionic cyclization of phosphonamides. A route to phosphonic acid derivatives with antitumor properties.
Ruiz-Gómez, Gloria; Francesch, Andrés; Iglesias, María José; López-Ortiz, Fernando; Cuevas, Carmen; Serrano-Ruiz, Manuel; Organic letters 10 (2008) 3981–3984; doi:10.1021/ol801463g

data_1504842
_publ_section_title
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 Dearomatizing anionic cyclization of phosphonamides. A route to
 phosphonic acid derivatives with antitumor properties.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              3981
_journal_page_last               3984
_journal_paper_doi               10.1021/ol801463g
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C26 H27 N2 O P'
_chemical_formula_weight         414.47
_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                 93.033(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5336(13)
_cell_length_b                   6.9286(5)
_cell_length_c                   18.8474(14)
_cell_measurement_reflns_used    383
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.909
_cell_measurement_theta_min      4.868
_cell_volume                     2156.0(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      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0805
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9066
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.895
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0184P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0763
_reflns_number_gt                2194
_reflns_number_total             3094
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801463g_si_005.cif
_cod_data_source_block           c:\sir97\fernando\685_2\r685_2m
_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_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1504842