#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:30:47 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180042 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/36/7033643.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_7033643
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_moiety         'C2 N5 O4, C4 H12 N'
_chemical_formula_sum            'C6 H12 N6 O4'
_chemical_formula_weight         232.22
_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                 92.6300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1515(3)
_cell_length_b                   17.1906(10)
_cell_length_c                   9.8599(5)
_cell_measurement_reflns_used    7015
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.2519
_cell_measurement_theta_min      2.3699
_cell_volume                     1041.57(10)
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_publication_material  'SHELXTL XL 2014/6 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XL 2014/6 (Bruker AXS)'
_computing_structure_solution    'SHELXTL XS 2013/1 (Bruker AXS)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0146
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3159
_diffrn_reflns_theta_full        30.47
_diffrn_reflns_theta_max         30.47
_diffrn_reflns_theta_min         2.37
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker TWINABS V2014/4'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0406
_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)+(0.0572P)²+0.2829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                2867
_reflns_number_total             3159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4dt03583f2.cif
_cod_data_source_block           C6H12N6O4
_cod_depositor_comments
'Adding full bibliography for 7033635--7033643.cif.'
_cod_database_code               7033643
#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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C3 0.2023(4) 0.42712(9) 0.86891(18) 0.0415(4) Uani d . . . 1.0 . .
H H3A 0.2097 0.4541 0.9566 0.062 Uiso calc U . R 1.0 . .
H H3B 0.0524 0.4283 0.8308 0.062 Uiso calc U . R 1.0 . .
H H3C 0.2984 0.4531 0.8065 0.062 Uiso calc U . R 1.0 . .
C C4 0.2689(3) 0.30501(10) 0.75384(14) 0.0308(3) Uani d . . . 1.0 . .
H H4A 0.3207 0.2515 0.7666 0.046 Uiso calc U . R 1.0 . .
H H4B 0.3638 0.3326 0.6928 0.046 Uiso calc U . R 1.0 . .
H H4C 0.1199 0.3043 0.7141 0.046 Uiso calc U . R 1.0 . .
C C5 0.4957(3) 0.34277(11) 0.95365(18) 0.0353(4) Uani d . . . 1.0 . .
H H5A 0.5374 0.2885 0.9703 0.053 Uiso calc U . R 1.0 . .
H H5B 0.4978 0.371 1.04 0.053 Uiso calc U . R 1.0 . .
H H5C 0.5987 0.3669 0.8935 0.053 Uiso calc U . R 1.0 . .
C C6 0.1193(3) 0.30403(11) 0.97743(19) 0.0378(4) Uani d . . . 1.0 . .
H H6A 0.1149 0.331 1.0648 0.057 Uiso calc U . R 1.0 . .
H H6B 0.1699 0.2505 0.9923 0.057 Uiso calc U . R 1.0 . .
H H6C -0.0267 0.3033 0.9334 0.057 Uiso calc U . R 1.0 . .
N N6 0.27214(17) 0.34569(6) 0.88835(10) 0.0169(2) Uani d . . . 1.0 . .
C C1 0.7680(2) 0.39433(7) 0.42610(12) 0.0152(2) Uani d . P D 0.9602(11) A 1
C C2 0.74165(19) 0.46874(8) 0.58067(12) 0.0157(2) Uani d . P D 0.9602(11) A 1
N N1 0.7414(2) 0.39849(7) 0.63943(11) 0.0212(2) Uani d . P D 0.9602(11) A 1
N N2 0.7584(2) 0.34801(6) 0.53445(11) 0.0212(2) Uani d . P D 0.9602(11) A 1
N N3 0.75917(16) 0.47107(6) 0.44636(11) 0.01488(19) Uani d . P D 0.9602(11) A 1
N N4 0.7886(2) 0.36165(7) 0.29179(12) 0.0193(2) Uani d . P D 0.9602(11) A 1
N N5 0.72257(18) 0.53863(7) 0.66087(12) 0.0205(2) Uani d . P D 0.9602(11) A 1
O O1 0.83042(19) 0.40703(7) 0.19958(11) 0.0273(2) Uani d . P D 0.9602(11) A 1
O O2 0.7646(2) 0.29171(6) 0.27647(12) 0.0338(3) Uani d . P D 0.9602(11) A 1
O O3 0.73521(17) 0.60172(6) 0.60315(11) 0.0266(2) Uani d . P D 0.9602(11) A 1
O O4 0.6933(2) 0.53090(8) 0.78278(13) 0.0323(3) Uani d . P D 0.9602(11) A 1
C C1' 0.774(5) 0.4323(11) 0.4591(19) 0.0152(2) Uani d . P D 0.0398(11) A 2
C C2' 0.740(5) 0.5084(12) 0.6096(17) 0.0157(2) Uani d . P D 0.0398(11) A 2
N N1' 0.745(5) 0.5510(11) 0.4956(19) 0.0212(2) Uani d . P D 0.0398(11) A 2
N N2' 0.766(5) 0.4997(12) 0.395(2) 0.0212(2) Uani d . P D 0.0398(11) A 2
N N3' 0.759(4) 0.4324(13) 0.5966(19) 0.01488(19) Uani d . P D 0.0398(11) A 2
N N4' 0.797(5) 0.3630(11) 0.379(2) 0.0193(2) Uani d . P D 0.0398(11) A 2
N N5' 0.726(6) 0.5466(12) 0.740(2) 0.0205(2) Uani d . P D 0.0398(11) A 2
O O1' 0.832(5) 0.3018(12) 0.451(2) 0.0273(2) Uani d . P D 0.0398(11) A 2
O O2' 0.810(8) 0.376(2) 0.257(2) 0.0338(3) Uani d . P D 0.0398(11) A 2
O O3' 0.707(5) 0.5023(13) 0.836(2) 0.0266(2) Uani d . P D 0.0398(11) A 2
O O4' 0.699(5) 0.6167(12) 0.740(2) 0.0323(3) Uani d . P D 0.0398(11) A 2
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
N6 C3 H3A 109.5
N6 C3 H3B 109.5
H3A C3 H3B 109.5
N6 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
N6 C4 H4A 109.5
N6 C4 H4B 109.5
H4A C4 H4B 109.5
N6 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N6 C5 H5A 109.5
N6 C5 H5B 109.5
H5A C5 H5B 109.5
N6 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N6 C6 H6A 109.5
N6 C6 H6B 109.5
H6A C6 H6B 109.5
N6 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C3 N6 C5 110.20(12)
C3 N6 C6 110.08(14)
C5 N6 C6 108.75(12)
C3 N6 C4 109.63(11)
C5 N6 C4 109.93(11)
C6 N6 C4 108.21(12)
N3 C1 N2 117.75(12)
N3 C1 N4 121.69(11)
N2 C1 N4 120.56(11)
N3 C1 C2 41.39(7)
N2 C1 C2 76.35(8)
N4 C1 C2 163.09(10)
N3 C2 N1 117.26(12)
N3 C2 N5 122.02(12)
N1 C2 N5 120.72(11)
N3 C2 C1 41.45(7)
N1 C2 C1 75.81(8)
N5 C2 C1 163.46(10)
C2 N1 N2 104.17(10)
C1 N2 N1 103.66(10)
C2 N3 C1 97.16(11)
O2 N4 O1 124.06(13)
O2 N4 C1 118.69(11)
O1 N4 C1 117.25(11)
O3 N5 O4 124.24(13)
O3 N5 C2 118.13(11)
O4 N5 C2 117.62(12)
N2' C1' N3' 118.2(14)
N2' C1' N4' 117.8(15)
N3' C1' N4' 124.1(17)
N2' C1' C2' 77.2(10)
N3' C1' C2' 41.0(8)
N4' C1' C2' 165.1(15)
N3' C2' N1' 116.9(14)
N3' C2' N5' 122.9(16)
N1' C2' N5' 120.1(16)
N3' C2' C1' 42.7(8)
N1' C2' C1' 74.2(10)
N5' C2' C1' 165.5(16)
N2' N1' C2' 105.6(15)
C1' N2' N1' 103.1(15)
C2' N3' C1' 96.2(13)
O2' N4' O1' 132.(2)
O2' N4' C1' 114.(2)
O1' N4' C1' 113.2(18)
O4' N5' O3' 127.(2)
O4' N5' C2' 117.3(19)
O3' N5' C2' 114.6(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 N6 1.4741(18)
C3 H3A 0.98
C3 H3B 0.98
C3 H3C 0.98
C4 N6 1.4986(16)
C4 H4A 0.98
C4 H4B 0.98
C4 H4C 0.98
C5 N6 1.4923(18)
C5 H5A 0.98
C5 H5B 0.98
C5 H5C 0.98
C6 N6 1.4979(18)
C6 H6A 0.98
C6 H6B 0.98
C6 H6C 0.98
C1 N3 1.3356(15)
C1 N2 1.3360(15)
C1 N4 1.4495(17)
C1 C2 2.0019(17)
C2 N3 1.3341(15)
C2 N1 1.3395(16)
C2 N5 1.4460(16)
N1 N2 1.3584(15)
N4 O2 1.2198(16)
N4 O1 1.2341(15)
N5 O3 1.2290(16)
N5 O4 1.2307(18)
C1' N2' 1.319(17)
C1' N3' 1.363(17)
C1' N4' 1.440(16)
C1' C2' 1.997(15)
C2' N3' 1.318(17)
C2' N1' 1.343(17)
C2' N5' 1.452(16)
N1' N2' 1.338(17)
N4' O2' 1.225(18)
N4' O1' 1.282(17)
N5' O4' 1.218(17)
N5' O3' 1.223(17)
