Intramolecular General Acid Catalysis of the Hydrolysis of 2-(2'-Imidazolium)phenyl Phosphate, and Bond Length-Reactivity Correlations for Reactions of Phosphate Monoester Monoanions
Tiago A. S. Brandão; Elisa S. Orth; Willian R. Rocha; Adailton J. Bortoluzzi; Clifford A. Bunton; Faruk Nome; Journal of Organic Chemistry 72 (2007) 3800–3807; doi:10.1021/jo070090r

data_4022899
_publ_contact_author_address
;
    Depto. de Qu\'imica - UFSC 
    88040 - 900 Florian\'opolis, SC 
    Brazil
;
_publ_contact_author_email       faruk@qmc.ufsc.br
_publ_contact_author_fax         +55-48-33316849
_publ_contact_author_name        'Faruk Nome'
_publ_contact_author_phone       +55-48-33316850
_publ_section_title
;
 Intramolecular General Acid Catalysis of the Hydrolysis of
 2-(2'-Imidazolium)phenyl Phosphate, and Bond Length-Reactivity
 Correlations for Reactions of Phosphate Monoester Monoanions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3800
_journal_page_last               3807
_journal_paper_doi               10.1021/jo070090r
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C9 H9 N2 O4 P'
_chemical_formula_weight         240.15
_chemical_name_systematic
;
2-(2'-imidazolium)phenyl hydrogen phosphate
;
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL97 and manual editing'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   9.0850(9)
_cell_length_b                   9.0850(9)
_cell_length_c                   20.973(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.41
_cell_measurement_theta_min      6.85
_cell_volume                     1499.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_method       \w--2\q
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2667
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.19(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1228
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0438P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0726
_reflns_number_gt                1029
_reflns_number_total             1228
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070090rsi20070116_020424.cif
_cod_data_source_block           C9H9N2O4P
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
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_database_code               4022899