Synthesis and Biological Evaluation of a Phosphonate Analog of the Natural Acetyl Cholinesterase Inhibitor Cyclophostin
Saibal Bandyopadhyay; Supratik Dutta; Christopher D. Spilling; Cynthia M. Dupureur; Nigam P. Rath; Journal of Organic Chemistry 73 (2008) 8386–8391; doi:10.1021/jo801453v

data_4023806
_publ_section_title
;
 Synthesis and Biological Evaluation of a Phosphonate Analog
 of the Natural Acetyl Cholinesterase Inhibitor Cyclophostin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8386
_journal_page_last               8391
_journal_paper_doi               10.1021/jo801453v
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C9 H13 O5 P'
_chemical_formula_weight         232.16
_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                 100.383(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3255(6)
_cell_length_b                   8.1275(4)
_cell_length_c                   10.9806(5)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      3.10
_cell_volume                     994.19(8)
_computing_cell_refinement       'Bruker-Apex II (Bruker, 2006)'
_computing_data_collection       'Bruker-Apex II (Bruker, 2006)'
_computing_data_reduction        'Bruker-SAINT   (Bruker, 2006)'
_computing_molecular_graphics    'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_computing_publication_material  'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_computing_structure_refinement  'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_computing_structure_solution    'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_diffrn_ambient_temperature      100(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     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31819
_diffrn_reflns_theta_full        30.41
_diffrn_reflns_theta_max         30.41
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_correction_T_min  0.9074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2007/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.4918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                2637
_reflns_number_total             3012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801453v_si_002.cif
_cod_data_source_block           s10607
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023806