#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/34/2233478.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2233478
loop_
_publ_author_name
'Ahmed, Safaa A.'
'Haque, Rosenani A.'
'Zetty, Zulikha H.'
'Fun, Hoong-Kun'
'Loh, Wan-Sin'
_publ_section_title
;
 2-[(2,4,4,6,6-Pentachloro-1,3,5,2λ⁵,4λ⁵,6λ⁵-triazatriphosphinin-2-yl)azanidyl]pyridinium
;
_journal_coeditor_code           HB6587
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o306
_journal_paper_doi               10.1107/S160053681200013X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C5 H5 Cl5 N5 P3'
_chemical_formula_moiety         'C5 H5 Cl5 N5 P3'
_chemical_formula_sum            'C5 H5 Cl5 N5 P3'
_chemical_formula_weight         405.30
_chemical_name_systematic
;
2-[(2,4,4,6,6-Pentachloro-1,3,5,2λ⁵,4λ⁵,6λ⁵-triazatriphosphinin-
2-yl)azanidyl]pyridinium
;
_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                 119.3550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.86770(10)
_cell_length_b                   14.7225(2)
_cell_length_c                   12.3564(2)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      32.63
_cell_measurement_theta_min      2.37
_cell_volume                     1406.05(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19432
_diffrn_reflns_theta_full        32.64
_diffrn_reflns_theta_max         32.64
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  0.6396
_exptl_absorpt_correction_T_min  0.4990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.386
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         5116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0234
_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)+(0.0211P)²+1.0751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0605
_reflns_number_gt                4806
_reflns_number_total             5116
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6587.cif
_cod_data_source_block           I
_cod_original_cell_volume        1406.05(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233478
_cod_database_fobs_code          2233478
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 1.37616(5) 0.29414(2) 0.46163(3) 0.02552(7) Uani d . 1 1
Cl Cl2 1.44578(4) 0.19325(3) 0.27089(3) 0.02419(7) Uani d . 1 1
Cl Cl3 0.89064(4) 0.22782(2) -0.05598(3) 0.02220(7) Uani d . 1 1
Cl Cl4 0.77111(4) 0.35825(2) 0.08438(3) 0.02138(6) Uani d . 1 1
Cl Cl5 0.99461(4) -0.00326(2) 0.13895(3) 0.01986(6) Uani d . 1 1
P P1 1.25273(4) 0.22143(2) 0.30552(3) 0.01580(6) Uani d . 1 1
P P2 0.92671(4) 0.25229(2) 0.11553(3) 0.01506(6) Uani d . 1 1
P P3 0.99248(4) 0.09616(2) 0.25490(3) 0.01336(6) Uani d . 1 1
N N1 1.18802(13) 0.13083(8) 0.33652(9) 0.01774(19) Uani d . 1 1
N N2 1.12016(15) 0.28591(8) 0.19854(10) 0.0216(2) Uani d . 1 1
N N3 0.85908(13) 0.17106(8) 0.16243(9) 0.01651(18) Uani d . 1 1
N N4 0.93798(13) 0.04813(7) 0.34645(9) 0.01398(17) Uani d . 1 1
N N5 0.75893(13) -0.03097(7) 0.39730(9) 0.01419(17) Uani d . 1 1
H H1 0.8457 -0.0360 0.4677 0.017 Uiso d R 1 1
C C1 0.78001(15) 0.01276(8) 0.30878(10) 0.01275(18) Uani d . 1 1
C C2 0.63220(16) 0.01682(9) 0.18857(10) 0.0171(2) Uani d . 1 1
H H2A 0.6394 0.0459 0.1244 0.021 Uiso calc R 1 1
C C3 0.47895(16) -0.02188(10) 0.16644(11) 0.0200(2) Uani d . 1 1
H H3A 0.3833 -0.0190 0.0873 0.024 Uiso calc R 1 1
C C4 0.46472(16) -0.06569(10) 0.26157(11) 0.0212(2) Uani d . 1 1
H H4A 0.3608 -0.0916 0.2469 0.025 Uiso calc R 1 1
C C5 0.60793(16) -0.06919(9) 0.37649(11) 0.0190(2) Uani d . 1 1
H H5A 0.6018 -0.0981 0.4412 0.023 Uiso calc R 1 1
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'
Cl Cl 0.1484 0.1585 '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
N1 P1 N2 120.13(6)
N1 P1 Cl1 108.18(4)
N2 P1 Cl1 108.41(5)
N1 P1 Cl2 109.20(5)
N2 P1 Cl2 107.98(5)
Cl1 P1 Cl2 101.32(2)
N3 P2 N2 119.12(6)
N3 P2 Cl4 108.31(4)
N2 P2 Cl4 107.93(5)
N3 P2 Cl3 111.07(4)
N2 P2 Cl3 107.45(5)
Cl4 P2 Cl3 101.487(19)
N4 P3 N1 107.76(5)
N4 P3 N3 115.69(6)
N1 P3 N3 114.83(6)
N4 P3 Cl5 106.73(4)
N1 P3 Cl5 106.78(5)
N3 P3 Cl5 104.34(4)
P1 N1 P3 121.89(7)
P1 N2 P2 118.55(7)
P2 N3 P3 120.16(7)
C1 N4 P3 123.48(8)
C5 N5 C1 123.83(10)
C5 N5 H1 118.7
C1 N5 H1 117.4
N4 C1 N5 115.82(10)
N4 C1 C2 128.01(10)
N5 C1 C2 116.17(10)
C3 C2 C1 120.46(11)
C3 C2 H2A 119.8
C1 C2 H2A 119.8
C2 C3 C4 120.82(11)
C2 C3 H3A 119.6
C4 C3 H3A 119.6
C5 C4 C3 118.04(12)
C5 C4 H4A 121.0
C3 C4 H4A 121.0
N5 C5 C4 120.68(11)
N5 C5 H5A 119.7
C4 C5 H5A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 P1 1.9987(4)
Cl2 P1 2.0011(5)
Cl3 P2 2.0146(4)
Cl4 P2 1.9912(5)
Cl5 P3 2.0548(4)
P1 N1 1.5719(11)
P1 N2 1.5834(11)
P2 N3 1.5705(11)
P2 N2 1.5858(11)
P3 N4 1.5967(10)
P3 N1 1.6031(11)
P3 N3 1.6111(11)
N4 C1 1.3456(15)
N5 C5 1.3558(16)
N5 C1 1.3589(14)
N5 H1 0.8354
C1 C2 1.4209(15)
C2 C3 1.3718(18)
C2 H2A 0.9300
C3 C4 1.3996(18)
C3 H3A 0.9300
C4 C5 1.3652(17)
C4 H4A 0.9300
C5 H5A 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N5 H1 N4 3_756 0.84 2.16 2.9949(14) 177 yes
C2 H2A N3 . 0.93 2.55 3.1538(19) 123 yes
C5 H5A N1 3_756 0.93 2.50 3.2220(16) 135 yes
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
N2 P1 N1 P3 5.48(12)
Cl1 P1 N1 P3 130.57(7)
Cl2 P1 N1 P3 -119.97(7)
N4 P3 N1 P1 -144.81(8)
N3 P3 N1 P1 -14.28(11)
Cl5 P3 N1 P1 100.84(8)
N1 P1 N2 P2 -6.08(12)
Cl1 P1 N2 P2 -131.06(7)
Cl2 P1 N2 P2 119.94(7)
N3 P2 N2 P1 16.53(12)
Cl4 P2 N2 P1 140.46(7)
Cl3 P2 N2 P1 -110.81(8)
N2 P2 N3 P3 -26.66(11)
Cl4 P2 N3 P3 -150.41(6)
Cl3 P2 N3 P3 98.96(7)
N4 P3 N3 P2 151.37(7)
N1 P3 N3 P2 24.81(10)
Cl5 P3 N3 P2 -91.71(7)
N1 P3 N4 C1 178.60(10)
N3 P3 N4 C1 48.55(12)
Cl5 P3 N4 C1 -67.03(10)
P3 N4 C1 N5 175.77(9)
P3 N4 C1 C2 -5.33(18)
C5 N5 C1 N4 178.77(12)
C5 N5 C1 C2 -0.27(18)
N4 C1 C2 C3 -178.84(13)
N5 C1 C2 C3 0.06(18)
C1 C2 C3 C4 0.3(2)
C2 C3 C4 C5 -0.4(2)
C1 N5 C5 C4 0.1(2)
C3 C4 C5 N5 0.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657414
