#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/55/7205581.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_7205581
loop_
_publ_author_name
'Garg, Sonali'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 Trifluoromethyl- or pentafluorosulfanyl-substituted
 poly-1,2,3-triazole compounds as dense stable energetic materials
;
_journal_issue                   13
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              4787
_journal_paper_doi               10.1039/c0jm04229c
_journal_volume                  21
_journal_year                    2011
_chemical_formula_moiety         'C15 H15 F9 N10'
_chemical_formula_sum            'C15 H15 F9 N10'
_chemical_formula_weight         506.37
_chemical_name_systematic
; 
 tris(2-(4-(trifluoromethyl)-1H-1,2,3-triazol-1-yl)ethyl)amine 
;
_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_date             2010-06-23
_audit_creation_method
'from SHELXTL CIF, local template and enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 104.906(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7121(14)
_cell_length_b                   14.214(2)
_cell_length_c                   15.290(2)
_cell_measurement_temperature    100(2)
_cell_volume                     2039.7(5)
_computing_cell_refinement       'Bruker APEX2 v2009.3-0 (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 v2009.3-0 (Bruker, 2009)'
_computing_data_reduction
;
Bruker SAINT v7.60A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21138
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0376P)²+0.9602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                3785
_reflns_number_total             5063
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            0jm04229c.txt
_cod_data_source_block           shrv119
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        2039.8(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7205581
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_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
N1 N 1.23531(13) 0.63498(9) 0.24919(9) 0.0179(3) Uani 1 1 d . . .
C2 C 1.24833(16) 0.73336(11) 0.22251(11) 0.0219(3) Uani 1 1 d . . .
H2A H 1.3455 0.7437 0.2151 0.026 Uiso 1 1 calc R . .
H2B H 1.2357 0.7752 0.2716 0.026 Uiso 1 1 calc R . .
C3 C 1.14106(17) 0.76003(12) 0.13558(11) 0.0219(3) Uani 1 1 d . . .
H3A H 1.1645 0.8234 0.1167 0.026 Uiso 1 1 calc R . .
H3B H 1.1481 0.7150 0.0875 0.026 Uiso 1 1 calc R . .
N4 N 0.99393(14) 0.76033(9) 0.14473(9) 0.0189(3) Uani 1 1 d . . .
N5 N 0.96526(14) 0.78778(10) 0.22253(9) 0.0236(3) Uani 1 1 d . . .
N6 N 0.82595(14) 0.79059(10) 0.20795(9) 0.0239(3) Uani 1 1 d . . .
C7 C 0.76742(17) 0.76597(11) 0.12057(11) 0.0214(3) Uani 1 1 d . . .
C8 C 0.87372(17) 0.74629(11) 0.07958(11) 0.0215(3) Uani 1 1 d . . .
H8 H 0.8645 0.7271 0.0188 0.026 Uiso 1 1 calc R . .
C9 C 0.61127(18) 0.76749(13) 0.08162(12) 0.0278(4) Uani 1 1 d . . .
F10 F 0.57704(11) 0.74031(9) -0.00488(7) 0.0402(3) Uani 1 1 d . . .
F11 F 0.55617(11) 0.85408(8) 0.08304(8) 0.0426(3) Uani 1 1 d . . .
F12 F 0.53991(11) 0.71223(9) 0.12516(9) 0.0459(3) Uani 1 1 d . . .
C13 C 1.29687(16) 0.57197(11) 0.19266(11) 0.0188(3) Uani 1 1 d . . .
H13A H 1.4021 0.5747 0.2138 0.023 Uiso 1 1 calc R . .
H13B H 1.2690 0.5947 0.1293 0.023 Uiso 1 1 calc R . .
C14 C 1.24919(16) 0.47065(11) 0.19506(11) 0.0207(3) Uani 1 1 d . . .
H14A H 1.3088 0.4300 0.1670 0.025 Uiso 1 1 calc R . .
H14B H 1.2642 0.4507 0.2589 0.025 Uiso 1 1 calc R . .
N15 N 1.09890(13) 0.45717(9) 0.14748(9) 0.0178(3) Uani 1 1 d . . .
N16 N 1.06282(15) 0.39153(10) 0.08229(9) 0.0228(3) Uani 1 1 d . . .
N17 N 0.92302(15) 0.39212(10) 0.05237(9) 0.0237(3) Uani 1 1 d . . .
C18 C 0.87165(16) 0.45839(11) 0.09958(10) 0.0189(3) Uani 1 1 d . . .
C19 C 0.98256(16) 0.50036(11) 0.16064(10) 0.0184(3) Uani 1 1 d . . .
H19 H 0.9784 0.5488 0.2027 0.022 Uiso 1 1 calc R . .
C20 C 0.71635(17) 0.47593(12) 0.08192(11) 0.0236(3) Uani 1 1 d . . .
F21 F 0.68866(11) 0.54013(9) 0.13808(8) 0.0435(3) Uani 1 1 d . . .
F22 F 0.64416(12) 0.39912(8) 0.09191(10) 0.0526(4) Uani 1 1 d . . .
F23 F 0.65940(12) 0.50805(10) -0.00117(8) 0.0461(3) Uani 1 1 d . . .
C24 C 1.30619(16) 0.62183(12) 0.34550(10) 0.0222(3) Uani 1 1 d . . .
H24A H 1.3979 0.6562 0.3601 0.027 Uiso 1 1 calc R . .
H24B H 1.3273 0.5542 0.3572 0.027 Uiso 1 1 calc R . .
C25 C 1.21634(16) 0.65636(13) 0.40738(11) 0.0232(3) Uani 1 1 d . . .
H25A H 1.2718 0.6499 0.4712 0.028 Uiso 1 1 calc R . .
H25B H 1.1945 0.7239 0.3955 0.028 Uiso 1 1 calc R . .
N26 N 1.08265(13) 0.60385(9) 0.39399(9) 0.0189(3) Uani 1 1 d . . .
N27 N 1.08344(14) 0.50920(10) 0.39932(10) 0.0233(3) Uani 1 1 d . . .
N28 N 0.95089(14) 0.48163(10) 0.38816(10) 0.0236(3) Uani 1 1 d . . .
C29 C 0.86728(16) 0.55950(12) 0.37581(11) 0.0207(3) Uani 1 1 d . . .
C30 C 0.94928(16) 0.63791(12) 0.37894(10) 0.0197(3) Uani 1 1 d . . .
H30 H 0.9193 0.7017 0.3721 0.024 Uiso 1 1 calc R . .
C31 C 0.71070(17) 0.55297(13) 0.36255(12) 0.0268(4) Uani 1 1 d . . .
F32 F 0.67117(11) 0.54614(11) 0.43940(8) 0.0541(4) Uani 1 1 d . . .
F33 F 0.64503(11) 0.62846(8) 0.31911(8) 0.0407(3) Uani 1 1 d . . .
F34 F 0.65442(12) 0.47821(9) 0.31299(9) 0.0468(3) 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'
F F 0.0171 0.0103 '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
C24 N1 C2 110.33(12) . . ?
C24 N1 C13 110.77(12) . . ?
C2 N1 C13 109.77(12) . . ?
N1 C2 C3 113.17(13) . . ?
N1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.8 . . ?
N4 C3 C2 112.57(13) . . ?
N4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C8 N4 N5 111.16(13) . . ?
C8 N4 C3 127.62(13) . . ?
N5 N4 C3 120.74(13) . . ?
N6 N5 N4 107.26(12) . . ?
N5 N6 C7 108.15(13) . . ?
N6 C7 C8 109.25(14) . . ?
N6 C7 C9 121.27(14) . . ?
C8 C7 C9 129.41(16) . . ?
N4 C8 C7 104.17(14) . . ?
N4 C8 H8 127.9 . . ?
C7 C8 H8 127.9 . . ?
F12 C9 F10 107.17(15) . . ?
F12 C9 F11 105.72(14) . . ?
F10 C9 F11 106.39(14) . . ?
F12 C9 C7 113.63(14) . . ?
F10 C9 C7 111.27(14) . . ?
F11 C9 C7 112.20(15) . . ?
N1 C13 C14 112.99(12) . . ?
N1 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N15 C14 C13 112.54(13) . . ?
N15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
N15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
N16 N15 C19 111.02(13) . . ?
N16 N15 C14 119.66(12) . . ?
C19 N15 C14 129.28(13) . . ?
N17 N16 N15 107.58(12) . . ?
N16 N17 C18 107.87(13) . . ?
N17 C18 C19 109.45(14) . . ?
N17 C18 C20 121.03(14) . . ?
C19 C18 C20 129.52(15) . . ?
N15 C19 C18 104.07(14) . . ?
N15 C19 H19 128.0 . . ?
C18 C19 H19 128.0 . . ?
F21 C20 F22 106.87(14) . . ?
F21 C20 F23 106.17(14) . . ?
F22 C20 F23 106.87(14) . . ?
F21 C20 C18 111.32(13) . . ?
F22 C20 C18 112.54(14) . . ?
F23 C20 C18 112.66(14) . . ?
N1 C24 C25 112.72(13) . . ?
N1 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
N1 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
N26 C25 C24 112.17(13) . . ?
N26 C25 H25A 109.2 . . ?
C24 C25 H25A 109.2 . . ?
N26 C25 H25B 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C30 N26 N27 111.08(13) . . ?
C30 N26 C25 128.29(14) . . ?
N27 N26 C25 120.59(13) . . ?
N28 N27 N26 107.44(12) . . ?
N27 N28 C29 107.82(13) . . ?
N28 C29 C30 109.79(14) . . ?
N28 C29 C31 121.56(15) . . ?
C30 C29 C31 128.65(15) . . ?
N26 C30 C29 103.87(14) . . ?
N26 C30 H30 128.1 . . ?
C29 C30 H30 128.1 . . ?
F32 C31 F33 106.79(15) . . ?
F32 C31 F34 105.89(15) . . ?
F33 C31 F34 106.46(14) . . ?
F32 C31 C29 113.71(14) . . ?
F33 C31 C29 111.06(14) . . ?
F34 C31 C29 112.46(14) . . ?
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
N1 C24 1.468(2) . ?
N1 C2 1.471(2) . ?
N1 C13 1.4738(19) . ?
C2 C3 1.511(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N4 1.4711(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N4 C8 1.341(2) . ?
N4 N5 1.3473(18) . ?
N5 N6 1.3140(19) . ?
N6 C7 1.356(2) . ?
C7 C8 1.367(2) . ?
C7 C9 1.480(2) . ?
C8 H8 0.9500 . ?
C9 F12 1.333(2) . ?
C9 F10 1.335(2) . ?
C9 F11 1.344(2) . ?
C13 C14 1.516(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N15 1.4664(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N15 N16 1.3443(18) . ?
N15 C19 1.3457(19) . ?
N16 N17 1.3166(19) . ?
N17 C18 1.357(2) . ?
C18 C19 1.368(2) . ?
C18 C20 1.483(2) . ?
C19 H19 0.9500 . ?
C20 F21 1.327(2) . ?
C20 F22 1.327(2) . ?
C20 F23 1.329(2) . ?
C24 C25 1.524(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N26 1.466(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N26 C30 1.3460(19) . ?
N26 N27 1.3477(19) . ?
N27 N28 1.3141(19) . ?
N28 C29 1.357(2) . ?
C29 C30 1.363(2) . ?
C29 C31 1.484(2) . ?
C30 H30 0.9500 . ?
C31 F32 1.330(2) . ?
C31 F33 1.335(2) . ?
C31 F34 1.338(2) . ?
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
C24 N1 C2 C3 -161.33(12) . . . . ?
C13 N1 C2 C3 76.32(16) . . . . ?
N1 C2 C3 N4 67.17(17) . . . . ?
C2 C3 N4 C8 -153.34(15) . . . . ?
C2 C3 N4 N5 35.3(2) . . . . ?
C8 N4 N5 N6 0.63(18) . . . . ?
C3 N4 N5 N6 173.32(13) . . . . ?
N4 N5 N6 C7 -0.74(17) . . . . ?
N5 N6 C7 C8 0.60(19) . . . . ?
N5 N6 C7 C9 -176.57(15) . . . . ?
N5 N4 C8 C7 -0.25(18) . . . . ?
C3 N4 C8 C7 -172.32(15) . . . . ?
N6 C7 C8 N4 -0.20(18) . . . . ?
C9 C7 C8 N4 176.66(16) . . . . ?
N6 C7 C9 F12 -58.6(2) . . . . ?
C8 C7 C9 F12 124.86(19) . . . . ?
N6 C7 C9 F10 -179.67(15) . . . . ?
C8 C7 C9 F10 3.8(3) . . . . ?
N6 C7 C9 F11 61.3(2) . . . . ?
C8 C7 C9 F11 -115.3(2) . . . . ?
C24 N1 C13 C14 75.45(16) . . . . ?
C2 N1 C13 C14 -162.47(13) . . . . ?
N1 C13 C14 N15 70.66(17) . . . . ?
C13 C14 N15 N16 126.26(14) . . . . ?
C13 C14 N15 C19 -56.1(2) . . . . ?
C19 N15 N16 N17 0.40(17) . . . . ?
C14 N15 N16 N17 178.46(13) . . . . ?
N15 N16 N17 C18 -0.26(17) . . . . ?
N16 N17 C18 C19 0.04(18) . . . . ?
N16 N17 C18 C20 -179.65(14) . . . . ?
N16 N15 C19 C18 -0.36(17) . . . . ?
C14 N15 C19 C18 -178.19(14) . . . . ?
N17 C18 C19 N15 0.19(17) . . . . ?
C20 C18 C19 N15 179.84(16) . . . . ?
N17 C18 C20 F21 177.06(15) . . . . ?
C19 C18 C20 F21 -2.6(2) . . . . ?
N17 C18 C20 F22 57.1(2) . . . . ?
C19 C18 C20 F22 -122.51(19) . . . . ?
N17 C18 C20 F23 -63.8(2) . . . . ?
C19 C18 C20 F23 116.58(19) . . . . ?
C2 N1 C24 C25 79.04(16) . . . . ?
C13 N1 C24 C25 -159.20(13) . . . . ?
N1 C24 C25 N26 62.76(19) . . . . ?
C24 C25 N26 C30 -128.80(17) . . . . ?
C24 C25 N26 N27 53.76(19) . . . . ?
C30 N26 N27 N28 -0.27(17) . . . . ?
C25 N26 N27 N28 177.58(13) . . . . ?
N26 N27 N28 C29 0.02(17) . . . . ?
N27 N28 C29 C30 0.24(18) . . . . ?
N27 N28 C29 C31 -179.06(14) . . . . ?
N27 N26 C30 C29 0.40(17) . . . . ?
C25 N26 C30 C29 -177.24(14) . . . . ?
N28 C29 C30 N26 -0.38(18) . . . . ?
C31 C29 C30 N26 178.85(15) . . . . ?
N28 C29 C31 F32 83.0(2) . . . . ?
C30 C29 C31 F32 -96.1(2) . . . . ?
N28 C29 C31 F33 -156.49(15) . . . . ?
C30 C29 C31 F33 24.4(2) . . . . ?
N28 C29 C31 F34 -37.3(2) . . . . ?
C30 C29 C31 F34 143.55(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653744
