#------------------------------------------------------------------------------
#$Date: 2017-05-18 04:24:41 +0200 (jue 18 de may de 2017) $
#$Revision: 196724 $
#$URL: svn://www.crystallography.net/cod/cif/7/04/29/7042967.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_7042967
loop_
_publ_author_name
'Ma, Qing'
'Chen, Ya'
'Liao, Longyu'
'Lu, Huanchang'
'Fan, Guijuan'
'Huang, Jinglun'
_publ_section_title
;
 Energetic π-conjugated vinyl bridged triazoles: a thermally stable and
 insensitive heterocyclic cation
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01261F
_journal_year                    2017
_chemical_formula_moiety         'C6 H12 N10, 2(N O3)'
_chemical_formula_sum            'C6 H12 N12 O6'
_chemical_formula_weight         348.28
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-01-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.12.12 svn.r3370 for OlexSys, GUI svn.r5282)
;
_audit_update_record
;
2017-01-07 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.095(3)
_cell_length_b                   6.7677(12)
_cell_length_c                   13.289(2)
_cell_measurement_reflns_used    1639
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.780
_cell_measurement_theta_min      2.699
_cell_volume                     1357.6(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9013
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.699
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0768 before and 0.0636 after correction. The Ratio of minimum to maximum transmission is 0.8576. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1547
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0427
_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)+(0.0711P)²+0.1689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1165
_reflns_number_total             1547
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;

    mo_te-no3_0ma.res created by SHELXL-2014/7

TITL mo_TE-NO3_0ma in Pbcn
CELL 0.71073 15.0946 6.7677 13.2893 90 90 90
ZERR 4 0.0026 0.0012 0.0024 0 0 0
LATT 1
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,+Y,0.5-Z
SYMM 0.5-X,0.5-Y,0.5+Z
SFAC C H N O
UNIT 24 48 48 24
ISOR 0.005 0.01 O1
 
L.S. 20
PLAN  -2 0 0
TEMP 23
HTAB
BOND $H
CONF
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\mo_TE-NO3_0ma.hkl">
REM </olex2.extras>
 
WGHT    0.071100    0.168900
FVAR       0.14701
N1    3    0.845028   -0.000697    0.163519    11.00000    0.01847    0.05628 =
         0.02906    0.00428   -0.00013   -0.00156
AFIX  93
H1A   2    0.893281   -0.013586    0.197296    11.00000   -1.20000
H1B   2    0.847127    0.026458    0.100345    11.00000   -1.20000
AFIX   0
 
O1    4    0.539393    0.412733    0.342640    11.00000    0.03238    0.08894 =
         0.02484    0.00943   -0.00402    0.00096
O2    4    0.498597    0.269799    0.480351    11.00000    0.03369    0.06536 =
         0.03936    0.00343    0.00659   -0.01495
O3    4    0.635871    0.351656    0.458789    11.00000    0.02212    0.06402 =
         0.02781    0.00200   -0.00416   -0.00138
N4    3    0.688123   -0.009194    0.163359    11.00000    0.01861    0.03592 =
         0.02091    0.00049   -0.00087    0.00038
N2    3    0.751039   -0.064329    0.304699    11.00000    0.01830    0.04718 =
         0.02437    0.00237   -0.00318   -0.00004
AFIX  43
H2    2    0.791282   -0.080484    0.349764    11.00000   -1.20000
AFIX   0
N5    3    0.680464    0.038090    0.060941    11.00000    0.02823    0.05059 =
         0.02149    0.00238   -0.00285   -0.00065
AFIX   7
H5A   2    0.663749   -0.064495    0.027605    11.00000   -1.20000
H5B   2    0.641913    0.130761    0.053574    11.00000   -1.20000
AFIX   0
 
N6    3    0.556255    0.345401    0.426998    11.00000    0.02356    0.04738 =
         0.02356   -0.00431   -0.00036   -0.00156
C1    1    0.767812   -0.022573    0.208600    11.00000    0.02035    0.02919 =
         0.02464   -0.00111   -0.00178   -0.00063
C2    1    0.624152   -0.046152    0.235874    11.00000    0.01997    0.03536 =
         0.02422   -0.00150    0.00250    0.00037
C3    1    0.530455   -0.048012    0.214290    11.00000    0.02101    0.04461 =
         0.02568    0.00062   -0.00153    0.00042
AFIX  43
H3    2    0.512213   -0.049260    0.147450    11.00000   -1.20000
AFIX   0
N3    3    0.661534   -0.078498    0.323164    11.00000    0.02147    0.04858 =
         0.02491    0.00157    0.00087   -0.00094
HKLF 4
 
REM  mo_TE-NO3_0ma in Pbcn
REM R1 =  0.0427 for    1165 Fo > 4sig(Fo)  and  0.0620 for all    1547 data
REM    110 parameters refined using      6 restraints
 
END  
     
WGHT      0.0711      0.1690 

REM Instructions for potential hydrogen bonds
EQIV $1 -x+3/2, y-1/2, z
HTAB N1 O1_$1
EQIV $2 x+1/2, y-1/2, -z+1/2
HTAB N1 O1_$2
EQIV $3 -x+3/2, -y+1/2, z-1/2
HTAB N1 O3_$3
HTAB N2 O1_$1
HTAB N2 O3_$1
HTAB N2 N6_$1
EQIV $4 x, -y, z-1/2
HTAB N5 O3_$4
EQIV $5 -x+1, y, -z+1/2
HTAB N5 O2_$5

REM Highest difference peak  0.229,  deepest hole -0.298,  1-sigma level  0.061
Q1    1   0.5000 -0.1218  0.2500  10.50000  0.05    0.23
Q2    1   0.7298 -0.0319  0.1781  11.00000  0.05    0.23

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0427 for 1165 Fo > 4sig(Fo) and 0.0620 for all 9790 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.23, deepest hole -0.30
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0620
  REM R1_gt = 0.0427
  REM wR_ref = 0.1277
  REM GOOF = 1.037
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 9790
  REM Reflections_gt = 1165
  REM Parameters = n/a
  REM Hole = -0.30
  REM Peak = 0.23
  REM Flack = n/a

  
;
_cod_data_source_file            c7dt01261f2.cif
_cod_data_source_block           mo_te-no3_0ma
_cod_database_code               7042967
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Rotating group:
 N5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.84503(11) -0.0007(3) 0.16352(12) 0.0346(4) Uani 1 1 d . .
H1A H 0.8933 -0.0136 0.1973 0.042 Uiso 1 1 calc R .
H1B H 0.8471 0.0265 0.1003 0.042 Uiso 1 1 calc R .
O1 O 0.53939(11) 0.4127(3) 0.34264(10) 0.0487(4) Uani 1 1 d . U
O2 O 0.49860(9) 0.2698(2) 0.48035(11) 0.0461(4) Uani 1 1 d . .
O3 O 0.63587(9) 0.3517(2) 0.45879(9) 0.0380(4) Uani 1 1 d . .
N4 N 0.68812(9) -0.0092(2) 0.16336(10) 0.0251(3) Uani 1 1 d . .
N2 N 0.75104(10) -0.0643(2) 0.30470(11) 0.0299(4) Uani 1 1 d . .
H2 H 0.7913 -0.0805 0.3498 0.036 Uiso 1 1 calc R .
N5 N 0.68046(11) 0.0381(2) 0.06094(10) 0.0334(4) Uani 1 1 d . .
H5A H 0.6637 -0.0645 0.0276 0.040 Uiso 1 1 d GR .
H5B H 0.6419 0.1308 0.0536 0.040 Uiso 1 1 d GR .
N6 N 0.55626(10) 0.3454(2) 0.42700(11) 0.0315(4) Uani 1 1 d . .
C1 C 0.76781(12) -0.0226(2) 0.20860(13) 0.0247(4) Uani 1 1 d . .
C2 C 0.62415(12) -0.0462(2) 0.23587(13) 0.0265(4) Uani 1 1 d . .
C3 C 0.53045(12) -0.0480(3) 0.21429(14) 0.0304(4) Uani 1 1 d . .
H3 H 0.5122 -0.0493 0.1474 0.037 Uiso 1 1 calc R .
N3 N 0.66153(11) -0.0785(2) 0.32316(11) 0.0317(4) Uani 1 1 d . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0185(9) 0.0563(10) 0.0291(8) 0.0043(6) -0.0001(6) -0.0016(7)
O1 0.0324(9) 0.0889(12) 0.0248(7) 0.0094(7) -0.0040(6) 0.0010(7)
O2 0.0337(9) 0.0654(10) 0.0394(8) 0.0034(7) 0.0066(6) -0.0150(7)
O3 0.0221(8) 0.0640(9) 0.0278(7) 0.0020(6) -0.0042(5) -0.0014(6)
N4 0.0186(8) 0.0359(8) 0.0209(7) 0.0005(5) -0.0009(6) 0.0004(6)
N2 0.0183(8) 0.0472(9) 0.0244(7) 0.0024(6) -0.0032(6) 0.0000(6)
N5 0.0282(10) 0.0506(10) 0.0215(7) 0.0024(6) -0.0028(6) -0.0007(7)
N6 0.0236(9) 0.0474(9) 0.0236(7) -0.0043(6) -0.0004(6) -0.0016(6)
C1 0.0203(9) 0.0292(8) 0.0246(8) -0.0011(6) -0.0018(7) -0.0006(6)
C2 0.0200(9) 0.0354(9) 0.0242(8) -0.0015(6) 0.0025(7) 0.0004(7)
C3 0.0210(10) 0.0446(10) 0.0257(9) 0.0006(7) -0.0015(7) 0.0004(7)
N3 0.0215(9) 0.0486(9) 0.0249(8) 0.0016(6) 0.0009(6) -0.0009(6)
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'
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
H1A N1 H1B 120.0 .
C1 N1 H1A 120.0 .
C1 N1 H1B 120.0 .
C1 N4 N5 121.44(14) .
C1 N4 C2 107.42(14) .
C2 N4 N5 131.14(14) .
C1 N2 H2 124.1 .
C1 N2 N3 111.85(15) .
N3 N2 H2 124.1 .
N4 N5 H5A 109.8 .
N4 N5 H5B 109.4 .
H5A N5 H5B 109.3 .
O1 N6 O3 118.84(15) .
O2 N6 O1 121.91(16) .
O2 N6 O3 119.24(15) .
N1 C1 N4 125.35(16) .
N1 C1 N2 128.84(17) .
N2 C1 N4 105.80(15) .
N4 C2 C3 123.08(15) .
N3 C2 N4 110.24(16) .
N3 C2 C3 126.68(17) .
C2 C3 H3 118.7 .
C3 C3 C2 122.6(2) 3_655
C3 C3 H3 118.7 3_655
C2 N3 N2 104.69(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 H1A 0.8600 .
N1 H1B 0.8600 .
N1 C1 1.319(2) .
O1 N6 1.237(2) .
O2 N6 1.2337(19) .
O3 N6 1.2746(19) .
N4 N5 1.4030(19) .
N4 C1 1.348(2) .
N4 C2 1.387(2) .
N2 H2 0.8600 .
N2 C1 1.332(2) .
N2 N3 1.376(2) .
N5 H5A 0.8613 .
N5 H5B 0.8611 .
C2 C3 1.443(3) .
C2 N3 1.308(2) .
C3 C3 1.321(4) 3_655
C3 H3 0.9300 .
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_4
N4 C2 C3 C3 -167.59(11) 3_655
N4 C2 N3 N2 -0.86(18) .
N5 N4 C1 N1 -2.4(3) .
N5 N4 C1 N2 178.54(15) .
N5 N4 C2 C3 2.2(3) .
N5 N4 C2 N3 -178.03(17) .
C1 N4 C2 C3 -178.83(16) .
C1 N4 C2 N3 0.89(19) .
C1 N2 N3 C2 0.5(2) .
C2 N4 C1 N1 178.55(17) .
C2 N4 C1 N2 -0.51(18) .
C3 C2 N3 N2 178.85(17) .
N3 N2 C1 N1 -179.02(18) .
N3 N2 C1 N4 -0.01(19) .
N3 C2 C3 C3 12.7(2) 3_655
