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_1504840
_publ_section_title
;
 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            'C29 H31 N2 O2.5 P'
_chemical_formula_weight         478.53
_chemical_name_systematic
; 
 ? 
;
_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                83.225(2)
_cell_angle_beta                 89.079(2)
_cell_angle_gamma                79.9980(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2490(5)
_cell_length_b                   10.8247(8)
_cell_length_c                   16.9512(11)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.120
_cell_measurement_theta_min      4.779
_cell_volume                     1300.75(16)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5906
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.578
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.264
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0810
_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^)+(0.0997P)^2^+0.1116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2015
_refine_ls_wR_factor_ref         0.2170
_reflns_number_gt                2942
_reflns_number_total             3615
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801463g_si_003.cif
_cod_data_source_block           c:\sir97\fernando\r280fr1\r280fr1m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_cell_volume        1300.76(16)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C29 H31 N2 O2.50 P'
_cod_database_code               1504840