#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:30:47 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180042 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/36/7033640.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_7033640
loop_
_publ_author_name
'Haiges, R.'
'Bélanger-Chabot, G'
'Kaplan, S. M.'
'Christe, K. O.'
_publ_section_title
;
 Synthesis and structural characterization of
 3,5-dinitro-1,2,4-triazolates.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2978
_journal_page_last               2988
_journal_paper_doi               10.1039/c4dt03583f
_journal_volume                  44
_journal_year                    2015
_chemical_formula_sum            'C26 H20 N5 O4 P'
_chemical_formula_weight         497.44
_chemical_name_common
'Tetraphenylphosphonium 3,5-dinitro-1,2,4 triazolate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-01-02 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.0410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2261(5)
_cell_length_b                   15.0086(7)
_cell_length_c                   13.8078(6)
_cell_measurement_reflns_used    50180
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      1.82
_cell_volume                     2317.45(18)
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXTL XS 2013/1 (Bruker AXS)'
_diffrn_ambient_temperature      100.(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            50180
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         1.82
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.264
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0397P)²+1.1073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                4600
_reflns_number_total             5872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4dt03583f2.cif
_cod_data_source_block           TPPDNT
_cod_depositor_comments
'Adding full bibliography for 7033635--7033643.cif.'
_cod_database_code               7033640
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.18798(13) 0.83189(10) 0.41096(10) 0.0179(3) Uani d . . 1
C C2 0.16020(13) 0.86982(10) 0.27150(11) 0.0189(3) Uani d . . 1
N N1 0.24200(11) 0.79766(9) 0.50288(10) 0.0237(3) Uani d . . 1
N N2 0.07446(11) 0.85853(9) 0.40219(9) 0.0220(3) Uani d . . 1
N N3 0.05531(11) 0.88386(9) 0.30725(9) 0.0225(3) Uani d . . 1
N N4 0.17766(12) 0.89031(9) 0.17114(9) 0.0232(3) Uani d . . 1
N N5 0.24882(11) 0.83772(8) 0.33237(9) 0.0198(3) Uani d . . 1
O O1 0.08945(11) 0.91145(9) 0.11693(9) 0.0348(3) Uani d . . 1
O O2 0.28021(11) 0.88604(8) 0.14647(9) 0.0309(3) Uani d . . 1
O O3 0.17919(11) 0.79380(9) 0.57105(8) 0.0347(3) Uani d . . 1
O O4 0.34716(10) 0.77480(9) 0.50725(9) 0.0370(3) Uani d . . 1
C C3 0.16079(12) 0.29597(9) 0.72413(10) 0.0154(3) Uani d . . 1
C C4 0.10023(13) 0.31497(10) 0.63402(11) 0.0197(3) Uani d . . 1
H H5 0.1289 0.2926 0.576 0.024 Uiso calc U R 1
C C5 -0.00268(14) 0.36710(10) 0.62991(12) 0.0255(3) Uani d . . 1
H H4 -0.0453 0.3798 0.569 0.031 Uiso calc U R 1
C C6 -0.04280(14) 0.40039(11) 0.71473(13) 0.0273(4) Uani d . . 1
H H3 -0.1121 0.437 0.7113 0.033 Uiso calc U R 1
C C7 0.01652(14) 0.38114(10) 0.80449(12) 0.0255(3) Uani d . . 1
H H2 -0.0126 0.4037 0.8622 0.031 Uiso calc U R 1
C C8 0.11880(13) 0.32871(10) 0.80968(11) 0.0202(3) Uani d . . 1
H H1 0.16 0.3152 0.871 0.024 Uiso calc U R 1
C C9 0.31069(12) 0.17108(9) 0.83993(10) 0.0151(3) Uani d . . 1
C C10 0.20910(13) 0.12228(9) 0.86069(10) 0.0176(3) Uani d . . 1
H H6 0.1359 0.1285 0.8211 0.021 Uiso calc U R 1
C C11 0.21724(14) 0.06479(10) 0.93989(10) 0.0208(3) Uani d . . 1
H H7 0.1492 0.0316 0.9548 0.025 Uiso calc U R 1
C C12 0.32438(15) 0.05564(10) 0.99734(10) 0.0226(3) Uani d . . 1
H H8 0.3298 0.015 1.0503 0.027 Uiso calc U R 1
C C13 0.42336(14) 0.10529(10) 0.97801(11) 0.0216(3) Uani d . . 1
H H9 0.4957 0.0997 1.0188 0.026 Uiso calc U R 1
C C14 0.41768(13) 0.16334(9) 0.89936(10) 0.0177(3) Uani d . . 1
H H10 0.4857 0.1974 0.8861 0.021 Uiso calc U R 1
C C15 0.41948(12) 0.31892(9) 0.73757(9) 0.0150(3) Uani d . . 1
C C16 0.39146(13) 0.40975(9) 0.74134(10) 0.0168(3) Uani d . . 1
H H11 0.3104 0.4282 0.74 0.02 Uiso calc U R 1
C C17 0.48220(14) 0.47281(10) 0.74699(10) 0.0205(3) Uani d . . 1
H H12 0.4633 0.5344 0.7503 0.025 Uiso calc U R 1
C C18 0.60041(14) 0.44596(10) 0.74780(11) 0.0225(3) Uani d . . 1
H H13 0.6623 0.4893 0.751 0.027 Uiso calc U R 1
C C19 0.62893(14) 0.35603(10) 0.74394(11) 0.0221(3) Uani d . . 1
H H14 0.7102 0.3382 0.7445 0.026 Uiso calc U R 1
C C20 0.53935(13) 0.29228(10) 0.73921(10) 0.0183(3) Uani d . . 1
H H15 0.5591 0.2308 0.7371 0.022 Uiso calc U R 1
C C21 0.30728(12) 0.16568(9) 0.62837(10) 0.0146(3) Uani d . . 1
C C22 0.40426(13) 0.16498(10) 0.57166(10) 0.0181(3) Uani d . . 1
H H16 0.4672 0.2069 0.5834 0.022 Uiso calc U R 1
C C23 0.40796(14) 0.10232(10) 0.49772(10) 0.0205(3) Uani d . . 1
H H17 0.474 0.1013 0.4592 0.025 Uiso calc U R 1
C C24 0.31570(14) 0.04131(10) 0.47992(11) 0.0211(3) Uani d . . 1
H H18 0.3194 -0.002 0.4301 0.025 Uiso calc U R 1
C C25 0.21772(13) 0.04348(10) 0.53501(11) 0.0202(3) Uani d . . 1
H H19 0.1537 0.0027 0.5215 0.024 Uiso calc U R 1
C C26 0.21321(13) 0.10492(10) 0.60948(10) 0.0171(3) Uani d . . 1
H H20 0.1467 0.1059 0.6475 0.021 Uiso calc U R 1
P P1 0.30090(3) 0.23838(2) 0.73171(3) 0.01296(8) Uani d . . 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'
O O 0.0106 0.0060 '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
N2 C1 N5 117.42(13)
N2 C1 N1 120.60(13)
N5 C1 N1 121.98(13)
N3 C2 N5 117.24(13)
N3 C2 N4 121.23(13)
N5 C2 N4 121.52(13)
O4 N1 O3 124.43(14)
O4 N1 C1 117.94(13)
O3 N1 C1 117.63(13)
C1 N2 N3 103.89(12)
C2 N3 N2 104.01(12)
O1 N4 O2 124.61(14)
O1 N4 C2 117.88(13)
O2 N4 C2 117.51(13)
C2 N5 C1 97.43(12)
C4 C3 C8 120.52(13)
C4 C3 P1 120.54(11)
C8 C3 P1 118.67(11)
C5 C4 C3 119.29(14)
C5 C4 H5 120.4
C3 C4 H5 120.4
C6 C5 C4 119.92(15)
C6 C5 H4 120.0
C4 C5 H4 120.0
C5 C6 C7 121.01(14)
C5 C6 H3 119.5
C7 C6 H3 119.5
C6 C7 C8 119.65(15)
C6 C7 H2 120.2
C8 C7 H2 120.2
C7 C8 C3 119.60(14)
C7 C8 H1 120.2
C3 C8 H1 120.2
C14 C9 C10 120.48(13)
C14 C9 P1 121.37(11)
C10 C9 P1 118.06(10)
C11 C10 C9 119.04(13)
C11 C10 H6 120.5
C9 C10 H6 120.5
C12 C11 C10 120.32(14)
C12 C11 H7 119.8
C10 C11 H7 119.8
C13 C12 C11 120.45(14)
C13 C12 H8 119.8
C11 C12 H8 119.8
C12 C13 C14 120.41(14)
C12 C13 H9 119.8
C14 C13 H9 119.8
C13 C14 C9 119.26(14)
C13 C14 H10 120.4
C9 C14 H10 120.4
C16 C15 C20 119.68(13)
C16 C15 P1 119.27(11)
C20 C15 P1 121.05(11)
C17 C16 C15 119.98(13)
C17 C16 H11 120.0
C15 C16 H11 120.0
C18 C17 C16 119.98(14)
C18 C17 H12 120.0
C16 C17 H12 120.0
C17 C18 C19 120.39(14)
C17 C18 H13 119.8
C19 C18 H13 119.8
C20 C19 C18 120.26(14)
C20 C19 H14 119.9
C18 C19 H14 119.9
C19 C20 C15 119.70(14)
C19 C20 H15 120.2
C15 C20 H15 120.2
C22 C21 C26 120.16(13)
C22 C21 P1 122.39(11)
C26 C21 P1 117.34(10)
C23 C22 C21 119.46(13)
C23 C22 H16 120.3
C21 C22 H16 120.3
C24 C23 C22 120.39(13)
C24 C23 H17 119.8
C22 C23 H17 119.8
C23 C24 C25 120.07(14)
C23 C24 H18 120.0
C25 C24 H18 120.0
C26 C25 C24 120.23(14)
C26 C25 H19 119.9
C24 C25 H19 119.9
C25 C26 C21 119.66(13)
C25 C26 H20 120.2
C21 C26 H20 120.2
C3 P1 C15 108.78(7)
C3 P1 C9 108.00(6)
C15 P1 C9 110.48(6)
C3 P1 C21 109.99(6)
C15 P1 C21 111.25(6)
C9 P1 C21 108.29(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.3310(19)
C1 N5 1.3348(19)
C1 N1 1.4516(19)
C2 N3 1.3330(19)
C2 N5 1.3347(19)
C2 N4 1.4494(19)
N1 O4 1.2258(17)
N1 O3 1.2261(17)
N2 N3 1.3637(18)
N4 O1 1.2294(17)
N4 O2 1.2306(17)
C3 C4 1.394(2)
C3 C8 1.399(2)
C3 P1 1.7897(14)
C4 C5 1.392(2)
C4 H5 0.95
C5 C6 1.384(2)
C5 H4 0.95
C6 C7 1.385(2)
C6 H3 0.95
C7 C8 1.389(2)
C7 H2 0.95
C8 H1 0.95
C9 C14 1.3987(19)
C9 C10 1.4059(19)
C9 P1 1.7990(14)
C10 C11 1.390(2)
C10 H6 0.95
C11 C12 1.388(2)
C11 H7 0.95
C12 C13 1.383(2)
C12 H8 0.95
C13 C14 1.389(2)
C13 H9 0.95
C14 H10 0.95
C15 C16 1.4010(19)
C15 C20 1.4021(19)
C15 P1 1.7946(14)
C16 C17 1.388(2)
C16 H11 0.95
C17 C18 1.386(2)
C17 H12 0.95
C18 C19 1.389(2)
C18 H13 0.95
C19 C20 1.386(2)
C19 H14 0.95
C20 H15 0.95
C21 C22 1.3959(19)
C21 C26 1.4023(19)
C21 P1 1.8028(14)
C22 C23 1.391(2)
C22 H16 0.95
C23 C24 1.388(2)
C23 H17 0.95
C24 C25 1.392(2)
C24 H18 0.95
C25 C26 1.385(2)
C25 H19 0.95
C26 H20 0.95
