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#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/74/4307481.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_4307481
loop_
_publ_author_name
'Gregor Reeske'
'Alan H. Cowley'
_publ_contact_author_address
;
   Department of Chemistry and Biochemistry
   University of Texas-Austin
   1 University Station, A5300
   Austin, TX 78701
   USA 
;
_publ_contact_author_email       cowley@mail.utexas.edu
_publ_contact_author_fax         512-471-6822
_publ_contact_author_name
;
Alan H. Cowley
;
_publ_contact_author_phone       512-471-7710
_publ_section_title
;
One-Step Redox Route to N-Heterocyclic Phosphenium Ions
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1426
_journal_page_last               1430
_journal_paper_doi               10.1021/ic061956z
_journal_volume                  46
_journal_year                    2007
_chemical_formula_moiety         'C20 H24 N2 P, I3 '
_chemical_formula_sum            'C20 H24 I3 N2 P'
_chemical_formula_weight         704.08
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 112.69(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.647(4)
_cell_length_b                   7.5469(15)
_cell_length_c                   16.488(3)
_cell_measurement_temperature    153(2)
_cell_volume                     2485.1(10)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;
SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       φ-scan
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4601
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    3.844
_exptl_absorpt_correction_T_max  0.655
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'DENZO and Scalepack (Otwinoski and Minor, 1997)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.831
_refine_diff_density_min         -1.796
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0489P)²+14.2019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                2139
_reflns_number_total             2828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic061956zsi20061012_022725.cif
_cod_data_source_block           try1
_cod_original_sg_symbol_Hall     -c2yc
_cod_database_code               4307481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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 0.4683(2) 0.7482(6) 0.2206(3) 0.0424(11) Uani 1 1 d . . .
H1 H 0.4429 0.6442 0.1972 0.051 Uiso 1 1 calc R . .
C2 C 0.37732(19) 0.9522(5) 0.1344(3) 0.0272(8) Uani 1 1 d . . .
C3 C 0.3696(2) 0.9919(5) 0.0482(3) 0.0309(9) Uani 1 1 d . . .
C4 C 0.3048(2) 1.0156(6) -0.0134(3) 0.0366(10) Uani 1 1 d . . .
H4 H 0.2982 1.0413 -0.0726 0.044 Uiso 1 1 calc R . .
C5 C 0.2497(2) 1.0029(6) 0.0091(3) 0.0390(10) Uani 1 1 d . . .
C6 C 0.2595(2) 0.9642(6) 0.0950(3) 0.0391(10) Uani 1 1 d . . .
H6 H 0.2217 0.9555 0.1105 0.047 Uiso 1 1 calc R . .
C7 C 0.3232(2) 0.9376(6) 0.1597(3) 0.0327(9) Uani 1 1 d . . .
C8 C 0.4290(2) 1.0054(7) 0.0218(3) 0.0398(10) Uani 1 1 d . . .
H8A H 0.4132 1.0161 -0.0423 0.060 Uiso 1 1 calc R . .
H8B H 0.4567 0.8989 0.0411 0.060 Uiso 1 1 calc R . .
H8C H 0.4556 1.1100 0.0494 0.060 Uiso 1 1 calc R . .
C9 C 0.1794(2) 1.0263(8) -0.0603(4) 0.0579(16) Uani 1 1 d . . .
H9A H 0.1467 1.0098 -0.0333 0.087 Uiso 1 1 calc R . .
H9B H 0.1716 0.9384 -0.1070 0.087 Uiso 1 1 calc R . .
H9C H 0.1748 1.1457 -0.0853 0.087 Uiso 1 1 calc R . .
C10 C 0.3318(3) 0.8912(8) 0.2522(3) 0.0496(13) Uani 1 1 d . . .
H10A H 0.3455 0.7670 0.2640 0.074 Uiso 1 1 calc R . .
H10B H 0.2893 0.9089 0.2593 0.074 Uiso 1 1 calc R . .
H10C H 0.3662 0.9675 0.2936 0.074 Uiso 1 1 calc R . .
N1 N 0.44457(16) 0.9173(5) 0.1987(2) 0.0289(7) Uani 1 1 d . . .
P1 P 0.5000 1.0742(2) 0.2500 0.0301(3) Uani 1 2 d S . .
I1 I 0.5000 0.5000 0.5000 0.0724(2) Uani 1 2 d S . .
I2 I 0.40213(3) 0.37460(6) 0.33192(4) 0.0772(2) 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'
I I -0.4742 1.8119 '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
C1 C1 N1 111.4(2) 2_655 . ?
C1 C1 H1 124.3 2_655 . ?
N1 C1 H1 124.3 . . ?
C7 C2 C3 122.5(4) . . ?
C7 C2 N1 119.2(4) . . ?
C3 C2 N1 118.2(4) . . ?
C4 C3 C2 117.6(4) . . ?
C4 C3 C8 120.7(4) . . ?
C2 C3 C8 121.7(4) . . ?
C5 C4 C3 121.7(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C6 C5 C4 118.9(4) . . ?
C6 C5 C9 120.7(5) . . ?
C4 C5 C9 120.4(5) . . ?
C5 C6 C7 122.1(4) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C2 C7 C6 117.2(4) . . ?
C2 C7 C10 122.2(4) . . ?
C6 C7 C10 120.6(4) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 C2 121.8(3) . . ?
C1 N1 P1 113.9(3) . . ?
C2 N1 P1 124.3(3) . . ?
N1 P1 N1 89.4(2) . 2_655 ?
I2 I1 I2 180.0 . 5_666 ?
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 C1 1.342(9) 2_655 ?
C1 N1 1.371(6) . ?
C1 H1 0.9500 . ?
C2 C7 1.393(6) . ?
C2 C3 1.397(6) . ?
C2 N1 1.457(5) . ?
C3 C4 1.390(6) . ?
C3 C8 1.512(6) . ?
C4 C5 1.384(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(7) . ?
C5 C9 1.520(6) . ?
C6 C7 1.394(6) . ?
C6 H6 0.9500 . ?
C7 C10 1.504(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N1 P1 1.665(3) . ?
P1 N1 1.665(3) 2_655 ?
I1 I2 2.9214(12) . ?
I1 I2 2.9214(12) 5_666 ?
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
C7 C2 C3 C4 -0.5(6) . . . . ?
N1 C2 C3 C4 176.7(4) . . . . ?
C7 C2 C3 C8 -179.4(4) . . . . ?
N1 C2 C3 C8 -2.2(6) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C8 C3 C4 C5 179.6(4) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C3 C4 C5 C9 -178.9(4) . . . . ?
C4 C5 C6 C7 0.0(7) . . . . ?
C9 C5 C6 C7 178.4(4) . . . . ?
C3 C2 C7 C6 0.1(6) . . . . ?
N1 C2 C7 C6 -177.1(4) . . . . ?
C3 C2 C7 C10 178.7(4) . . . . ?
N1 C2 C7 C10 1.5(7) . . . . ?
C5 C6 C7 C2 0.2(7) . . . . ?
C5 C6 C7 C10 -178.5(5) . . . . ?
C1 C1 N1 C2 178.5(5) 2_655 . . . ?
C1 C1 N1 P1 0.0(7) 2_655 . . . ?
C7 C2 N1 C1 79.3(5) . . . . ?
C3 C2 N1 C1 -98.0(5) . . . . ?
C7 C2 N1 P1 -102.3(4) . . . . ?
C3 C2 N1 P1 80.4(4) . . . . ?
C1 N1 P1 N1 0.0(3) . . . 2_655 ?
C2 N1 P1 N1 -178.5(4) . . . 2_655 ?
