#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:20:15 +0100 (dom 24 de nov de 2019) $
#$Revision: 237444 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/71/7237139.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_7237139
loop_
_publ_author_name
'Tang, Yongxing'
'He, Chunlin'
'Imler, Gregory H.'
'Parrish, Damon A.'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 Ring closure of polynitroazoles via an N,N′-alkylene bridge:
 towards high thermally stable energetic compounds
;
_journal_issue                   18
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              8382
_journal_paper_doi               10.1039/C8TA02704H
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C6 H4 N8 O4'
_chemical_formula_sum            'C6 H4 N8 O4'
_chemical_formula_weight         252.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-19 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.517(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.326(5)
_cell_length_b                   6.678(3)
_cell_length_c                   12.126(5)
_cell_measurement_reflns_used    1506
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.623
_cell_measurement_theta_min      3.415
_cell_volume                     966.3(7)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_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  0.0256
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5479
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.977
_diffrn_reflns_theta_min         3.415
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1376
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0456
_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)+(0.0788P)²+0.3224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                903
_reflns_number_total             1376
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ta02704h2.cif
_cod_data_source_block           shrv596
_cod_original_cell_volume        966.3(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7237139
_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.
;
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67125(15) 0.6625(2) 0.57926(14) 0.0728(5) Uani 1 1 d . . . . .
O2 O 0.71023(16) 0.3749(3) 0.66325(13) 0.0805(5) Uani 1 1 d . . . . .
N3 N 0.67042(13) 0.4813(3) 0.58037(13) 0.0549(4) Uani 1 1 d . . . . .
C4 C 0.61494(14) 0.3805(3) 0.47485(13) 0.0434(4) Uani 1 1 d . . . . .
N5 N 0.60473(14) 0.1836(2) 0.47173(12) 0.0557(5) Uani 1 1 d . . . . .
N6 N 0.54975(13) 0.15730(18) 0.36261(12) 0.0470(4) Uani 1 1 d D . . . .
C7A C 0.4983(6) -0.0337(5) 0.3120(3) 0.0540(12) Uani 0.766(16) 1 d . . P A 1
H7A H 0.4215 -0.0430 0.3181 0.065 Uiso 0.766(16) 1 calc R U P A 1
H7B H 0.5399 -0.1470 0.3515 0.065 Uiso 0.766(16) 1 calc R U P A 1
C7B C 0.550(2) -0.0334(17) 0.3013(14) 0.069(5) Uani 0.234(16) 1 d D . P A 2
H7C H 0.5457 -0.1453 0.3508 0.083 Uiso 0.234(16) 1 calc R U P A 2
H7D H 0.6190 -0.0458 0.2766 0.083 Uiso 0.234(16) 1 calc R U P A 2
C8 C 0.52995(14) 0.33456(19) 0.30915(14) 0.0378(4) Uani 1 1 d . . . . .
N9 N 0.57093(11) 0.48306(18) 0.37965(11) 0.0412(4) 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'
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
_geom_angle_site_symmetry_3
O1 N3 O2 125.79(18) . .
O1 N3 C4 117.13(16) . .
O2 N3 C4 117.06(18) . .
N5 C4 N9 118.09(15) . .
N5 C4 N3 120.39(16) . .
N9 C4 N3 121.50(16) . .
C4 N5 N6 100.35(13) . .
N5 N6 C8 110.34(13) . .
N5 N6 C7B 123.1(6) . .
C8 N6 C7B 122.7(8) . .
N5 N6 C7A 125.33(19) . .
C8 N6 C7A 123.4(2) . .
N6 C7A C7A 107.1(4) . 2_655
N6 C7A H7A 110.3 . .
C7A C7A H7A 110.3 2_655 .
N6 C7A H7B 110.3 . .
C7A C7A H7B 110.3 2_655 .
H7A C7A H7B 108.5 . .
N6 C7B C7B 107.8(12) . 2_655
N6 C7B H7C 110.1 . .
C7B C7B H7C 110.1 2_655 .
N6 C7B H7D 110.1 . .
C7B C7B H7D 110.1 2_655 .
H7C C7B H7D 108.5 . .
N9 C8 N6 110.79(15) . .
N9 C8 C8 131.36(9) . 2_655
N6 C8 C8 117.84(10) . 2_655
C8 N9 C4 100.41(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N3 1.210(2) .
O2 N3 1.228(2) .
N3 C4 1.456(2) .
C4 N5 1.321(2) .
C4 N9 1.335(2) .
N5 N6 1.338(2) .
N6 C8 1.3423(19) .
N6 C7B 1.476(4) .
N6 C7A 1.487(3) .
C7A C7A 1.515(8) 2_655
C7A H7A 0.9700 .
C7A H7B 0.9700 .
C7B C7B 1.52(3) 2_655
C7B H7C 0.9700 .
C7B H7D 0.9700 .
C8 N9 1.3240(19) .
C8 C8 1.439(3) 2_655
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7A H7B N9 0.97 2.51 3.394(5) 151.4 1_545
C7B H7C N9 0.97 2.51 3.358(15) 145.3 1_545
C7B H7D O2 0.97 2.34 3.06(3) 130.4 7_656
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_4
O1 N3 C4 N5 -175.79(17) . .
O2 N3 C4 N5 2.8(2) . .
O1 N3 C4 N9 2.7(2) . .
O2 N3 C4 N9 -178.73(16) . .
N9 C4 N5 N6 0.9(2) . .
N3 C4 N5 N6 179.46(15) . .
C4 N5 N6 C8 -0.7(2) . .
C4 N5 N6 C7B 157.8(13) . .
C4 N5 N6 C7A -169.8(4) . .
N5 N6 C7A C7A -150.4(4) . 2_655
C8 N6 C7A C7A 41.9(8) . 2_655
N5 N6 C7B C7B 159.8(16) . 2_655
C8 N6 C7B C7B -44(3) . 2_655
N5 N6 C8 N9 0.3(2) . .
C7B N6 C8 N9 -158.3(12) . .
C7A N6 C8 N9 169.7(4) . .
N5 N6 C8 C8 -179.28(18) . 2_655
C7B N6 C8 C8 22.1(12) . 2_655
C7A N6 C8 C8 -9.9(4) . 2_655
N6 C8 N9 C4 0.23(17) . .
C8 C8 N9 C4 179.7(2) 2_655 .
N5 C4 N9 C8 -0.74(19) . .
N3 C4 N9 C8 -179.28(15) . .
