N-Phosphorylated Imidazolium Salts as Precursors to 2- and 5-Phosphorylated Imidazoles and New Imidazol-2-ylidenes Featuring the PNCN Unit
Anatolii P. Marchenko; Heorgii N. Koidan; Anastasiya N. Huryeva; Evgeniy V. Zarudnitskii; Aleksandr A. Yurchenko; Aleksandr N. Kostyuk; Journal of Organic Chemistry 75 (2010) 7141–7145; doi:10.1021/jo101177h

data_4025751
_publ_section_title
;
 N-Phosphorylated Imidazolium Salts as Precursors to 2- and
 5-Phosphorylated Imidazoles and New Imidazol-2-ylidenes Featuring the
 PNCN Unit
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7141
_journal_page_last               7145
_journal_paper_doi               10.1021/jo101177h
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C27 H58 N6 P2'
_chemical_formula_sum            'C27 H58 N6 P2'
_chemical_formula_weight         528.74
_chemical_melting_point          121.0(10)
_chemical_name_systematic
;
1,3-bis[bis[diisopropylamino)phosphino]-1H-imidazol-2-ylidene
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 110.324(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.7933(5)
_cell_length_b                   7.6796(3)
_cell_length_c                   17.9035(7)
_cell_measurement_reflns_used    3982
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.43
_cell_volume                     1649.47(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      173(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22717
_diffrn_reflns_theta_full        27.29
_diffrn_reflns_theta_max         27.29
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_correction_T_min  0.9403
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0380P)^2^+0.6853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                2731
_reflns_number_total             3707
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101177h_si_001.cif
_cod_data_source_block           ca
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '120-122' was changed to '121.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1649.46(11)
_cod_database_code               4025751