#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:39:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178436 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/57/4025751.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025751
loop_
_publ_author_name
'Anatolii P. Marchenko'
'Heorgii N. Koidan'
'Anastasiya N. Huryeva'
'Evgeniy V. Zarudnitskii'
'Aleksandr A. Yurchenko'
'Aleksandr N. Kostyuk'
_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/[σ²(Fo²)+(0.0380P)²+0.6853P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5000 0.2352(3) 0.2500 0.0227(5) Uani 1 2 d S . .
C2 C 0.55187(15) -0.0494(2) 0.27627(12) 0.0341(5) Uani 1 1 d . . .
H2 H 0.5948 -0.1469 0.2980 0.041 Uiso 1 1 calc R . .
C3 C 0.73056(15) 0.3536(2) 0.23234(10) 0.0299(4) Uani 1 1 d . . .
H3 H 0.6571 0.3886 0.2328 0.036 Uiso 1 1 calc R . .
C4 C 0.79492(19) 0.5210(3) 0.23260(14) 0.0504(6) Uani 1 1 d . . .
H4A H 0.8057 0.5837 0.2811 0.076 Uiso 1 1 calc R . .
H4B H 0.7535 0.5918 0.1880 0.076 Uiso 1 1 calc R . .
H4C H 0.8661 0.4928 0.2289 0.076 Uiso 1 1 calc R . .
C5 C 0.71041(18) 0.2488(3) 0.15637(11) 0.0431(5) Uani 1 1 d . . .
H5A H 0.7804 0.2084 0.1544 0.065 Uiso 1 1 calc R . .
H5B H 0.6746 0.3212 0.1109 0.065 Uiso 1 1 calc R . .
H5C H 0.6636 0.1508 0.1559 0.065 Uiso 1 1 calc R . .
C6 C 0.89582(14) 0.1790(3) 0.31679(12) 0.0365(5) Uani 1 1 d . . .
H6 H 0.9189 0.2272 0.2743 0.044 Uiso 1 1 calc R . .
C7 C 0.89893(19) -0.0180(3) 0.30992(16) 0.0561(7) Uani 1 1 d . . .
H7A H 0.8828 -0.0705 0.3534 0.084 Uiso 1 1 calc R . .
H7B H 0.9717 -0.0536 0.3116 0.084 Uiso 1 1 calc R . .
H7C H 0.8443 -0.0544 0.2604 0.084 Uiso 1 1 calc R . .
C8 C 0.97955(17) 0.2419(4) 0.39508(15) 0.0619(7) Uani 1 1 d . . .
H8A H 0.9790 0.3669 0.3965 0.093 Uiso 1 1 calc R . .
H8B H 1.0527 0.2020 0.3998 0.093 Uiso 1 1 calc R . .
H8C H 0.9600 0.1967 0.4385 0.093 Uiso 1 1 calc R . .
C9 C 0.70532(16) 0.2726(3) 0.50225(10) 0.0313(4) Uani 1 1 d . . .
H9 H 0.6920 0.3782 0.5283 0.038 Uiso 1 1 calc R . .
C10 C 0.61533(19) 0.1423(3) 0.50196(13) 0.0472(6) Uani 1 1 d . . .
H10A H 0.5437 0.1863 0.4696 0.071 Uiso 1 1 calc R . .
H10B H 0.6167 0.1254 0.5554 0.071 Uiso 1 1 calc R . .
H10C H 0.6289 0.0333 0.4807 0.071 Uiso 1 1 calc R . .
C11 C 0.82107(19) 0.2074(3) 0.55205(12) 0.0513(6) Uani 1 1 d . . .
H11A H 0.8369 0.1021 0.5291 0.077 Uiso 1 1 calc R . .
H11B H 0.8237 0.1847 0.6054 0.077 Uiso 1 1 calc R . .
H11C H 0.8755 0.2942 0.5530 0.077 Uiso 1 1 calc R . .
C12 C 0.66755(14) 0.5063(2) 0.39758(10) 0.0251(4) Uani 1 1 d . . .
H12 H 0.6588 0.5172 0.3412 0.030 Uiso 1 1 calc R . .
C13 C 0.55647(15) 0.5575(3) 0.40539(11) 0.0331(4) Uani 1 1 d . . .
H13A H 0.4995 0.4779 0.3753 0.050 Uiso 1 1 calc R . .
H13B H 0.5370 0.6734 0.3854 0.050 Uiso 1 1 calc R . .
H13C H 0.5630 0.5533 0.4604 0.050 Uiso 1 1 calc R . .
C14 C 0.76109(16) 0.6295(3) 0.44399(12) 0.0364(5) Uani 1 1 d . . .
H14A H 0.7719 0.6224 0.4997 0.055 Uiso 1 1 calc R . .
H14B H 0.7416 0.7466 0.4257 0.055 Uiso 1 1 calc R . .
H14C H 0.8287 0.5969 0.4358 0.055 Uiso 1 1 calc R . .
N1 N 0.58375(11) 0.12356(18) 0.29252(8) 0.0211(3) Uani 1 1 d . . .
N2 N 0.78232(11) 0.24783(19) 0.30421(8) 0.0260(3) Uani 1 1 d . . .
N3 N 0.69823(11) 0.32377(18) 0.42073(8) 0.0237(3) Uani 1 1 d . . .
P1 P 0.71821(3) 0.16484(6) 0.36363(3) 0.02200(13) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N1 102.96(19) 2_655 . ?
C2 C2 N1 107.17(9) 2_655 . ?
C2 C2 H2 126.4 2_655 . ?
N1 C2 H2 126.4 . . ?
N2 C3 C5 112.00(16) . . ?
N2 C3 C4 112.60(16) . . ?
C5 C3 C4 111.82(17) . . ?
N2 C3 H3 106.7 . . ?
C5 C3 H3 106.7 . . ?
C4 C3 H3 106.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C8 111.44(17) . . ?
N2 C6 C7 113.17(16) . . ?
C8 C6 C7 111.2(2) . . ?
N2 C6 H6 106.9 . . ?
C8 C6 H6 106.9 . . ?
C7 C6 H6 106.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C11 112.19(15) . . ?
N3 C9 C10 112.50(15) . . ?
C11 C9 C10 111.46(18) . . ?
N3 C9 H9 106.7 . . ?
C11 C9 H9 106.7 . . ?
C10 C9 H9 106.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C14 110.75(14) . . ?
N3 C12 C13 112.60(14) . . ?
C14 C12 C13 111.67(15) . . ?
N3 C12 H12 107.2 . . ?
C14 C12 H12 107.2 . . ?
C13 C12 H12 107.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C2 111.35(14) . . ?
C1 N1 P1 131.18(12) . . ?
C2 N1 P1 117.44(11) . . ?
C3 N2 C6 116.63(14) . . ?
C3 N2 P1 126.42(11) . . ?
C6 N2 P1 115.81(12) . . ?
C12 N3 C9 116.58(14) . . ?
C12 N3 P1 127.26(11) . . ?
C9 N3 P1 116.04(12) . . ?
N3 P1 N2 108.86(7) . . ?
N3 P1 N1 104.68(7) . . ?
N2 P1 N1 100.26(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3770(19) 2_655 ?
C1 N1 1.3770(19) . ?
C2 C2 1.334(3) 2_655 ?
C2 N1 1.390(2) . ?
C2 H2 0.9300 . ?
C3 N2 1.470(2) . ?
C3 C5 1.523(3) . ?
C3 C4 1.526(3) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N2 1.487(2) . ?
C6 C8 1.517(3) . ?
C6 C7 1.519(3) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N3 1.484(2) . ?
C9 C11 1.524(3) . ?
C9 C10 1.524(3) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N3 1.475(2) . ?
C12 C14 1.525(2) . ?
C12 C13 1.527(2) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 P1 1.7774(14) . ?
N2 P1 1.6784(15) . ?
N3 P1 1.6677(14) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 N1 C2 0.05(10) 2_655 . . . ?
N1 C1 N1 P1 -177.96(15) 2_655 . . . ?
C2 C2 N1 C1 -0.1(3) 2_655 . . . ?
C2 C2 N1 P1 178.18(18) 2_655 . . . ?
C5 C3 N2 C6 63.7(2) . . . . ?
C4 C3 N2 C6 -63.3(2) . . . . ?
C5 C3 N2 P1 -103.53(17) . . . . ?
C4 C3 N2 P1 129.44(16) . . . . ?
C8 C6 N2 C3 120.9(2) . . . . ?
C7 C6 N2 C3 -112.9(2) . . . . ?
C8 C6 N2 P1 -70.5(2) . . . . ?
C7 C6 N2 P1 55.8(2) . . . . ?
C14 C12 N3 C9 69.10(19) . . . . ?
C13 C12 N3 C9 -56.73(19) . . . . ?
C14 C12 N3 P1 -115.04(15) . . . . ?
C13 C12 N3 P1 119.12(15) . . . . ?
C11 C9 N3 C12 -120.25(18) . . . . ?
C10 C9 N3 C12 113.11(17) . . . . ?
C11 C9 N3 P1 63.42(19) . . . . ?
C10 C9 N3 P1 -63.22(18) . . . . ?
C12 N3 P1 N2 37.99(15) . . . . ?
C9 N3 P1 N2 -146.13(12) . . . . ?
C12 N3 P1 N1 -68.51(14) . . . . ?
C9 N3 P1 N1 107.37(12) . . . . ?
C3 N2 P1 N3 -76.47(16) . . . . ?
C6 N2 P1 N3 116.19(13) . . . . ?
C3 N2 P1 N1 33.04(16) . . . . ?
C6 N2 P1 N1 -134.30(13) . . . . ?
C1 N1 P1 N3 42.21(13) . . . . ?
C2 N1 P1 N3 -135.70(14) . . . . ?
C1 N1 P1 N2 -70.56(13) . . . . ?
C2 N1 P1 N2 111.53(14) . . . . ?
