#------------------------------------------------------------------------------
#$Date: 2019-11-23 22:39:34 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235391 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/63/7236314.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_7236314
loop_
_publ_author_name
'Zhang, Jiaheng'
'Yin, Ping'
'Mitchell, Lauren A.'
'Parrish, Damon A.'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 N-functionalized nitroxy/azido fused-ring azoles as high-performance
 energetic materials
;
_journal_issue                   19
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              7430
_journal_paper_doi               10.1039/C6TA02384C
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C6 H4 N10 O10'
_chemical_formula_sum            'C6 H4 N10 O10'
_chemical_formula_weight         376.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-01 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                98.6470(10)
_cell_angle_beta                 92.0850(10)
_cell_angle_gamma                109.154(2)
_cell_formula_units_Z            2
_cell_length_a                   6.4891(3)
_cell_length_b                   8.1203(4)
_cell_length_c                   13.7172(7)
_cell_measurement_reflns_used    3188
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      3.31
_cell_volume                     672.18(6)
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0132
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6438
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.441
_diffrn_reflns_theta_min         1.508
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0333
_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)+(0.0420P)²+0.2312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2270
_reflns_number_total             2732
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ta02384c2.cif
_cod_data_source_block           shrv306
_cod_database_code               7236314
_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   0.934
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N1A N -0.0674(2) 0.17712(16) 0.07767(9) 0.0313(3) Uani 1 1 d . .
C2A C 0.0302(2) 0.09593(19) 0.01363(11) 0.0282(3) Uani 1 1 d . .
N3A N 0.1998(2) 0.21665(16) -0.02012(9) 0.0285(3) Uani 1 1 d . .
N4A N 0.2171(2) 0.38154(16) 0.02481(9) 0.0307(3) Uani 1 1 d . .
C5A C 0.0542(2) 0.34618(19) 0.08077(11) 0.0292(3) Uani 1 1 d . .
N6A N 0.0133(2) 0.48776(17) 0.14687(10) 0.0353(3) Uani 1 1 d . .
O7A O 0.1235(2) 0.63999(15) 0.14180(9) 0.0443(3) Uani 1 1 d . .
O8A O -0.1243(3) 0.44517(18) 0.20417(11) 0.0596(4) Uani 1 1 d . .
C9A C 0.3617(3) 0.1968(2) -0.08830(12) 0.0342(3) Uani 1 1 d . .
H9A1 H 0.5074 0.2517 -0.0541 0.041 Uiso 1 1 calc R U
H9A2 H 0.3383 0.0720 -0.1091 0.041 Uiso 1 1 calc R U
O10A O 0.34883(19) 0.27483(15) -0.17300(8) 0.0395(3) Uani 1 1 d . .
N11A N 0.1760(2) 0.1682(2) -0.24664(10) 0.0400(3) Uani 1 1 d . .
O12A O 0.0395(2) 0.04478(17) -0.22359(10) 0.0504(3) Uani 1 1 d . .
O13A O 0.1930(3) 0.2233(2) -0.32310(10) 0.0585(4) Uani 1 1 d . .
N1B N 0.5168(2) 0.31474(18) 0.40927(9) 0.0338(3) Uani 1 1 d . .
C2B C 0.4771(2) 0.4591(2) 0.44803(11) 0.0307(3) Uani 1 1 d . .
N3B N 0.3840(2) 0.52066(17) 0.37803(9) 0.0326(3) Uani 1 1 d . .
N4B N 0.3584(2) 0.41165(18) 0.28970(9) 0.0351(3) Uani 1 1 d . .
C5B C 0.4413(3) 0.2948(2) 0.31450(11) 0.0319(3) Uani 1 1 d . .
N6B N 0.4553(2) 0.14985(19) 0.24122(10) 0.0381(3) Uani 1 1 d . .
O7B O 0.4019(2) 0.14698(19) 0.15499(9) 0.0512(3) Uani 1 1 d . .
O8B O 0.5223(3) 0.0423(2) 0.27167(10) 0.0623(4) Uani 1 1 d . .
C9B C 0.3268(3) 0.6802(2) 0.38375(12) 0.0386(4) Uani 1 1 d . .
H9B1 H 0.4439 0.7810 0.4205 0.046 Uiso 1 1 calc R U
H9B2 H 0.3018 0.7038 0.3179 0.046 Uiso 1 1 calc R U
O10B O 0.1310(2) 0.64885(16) 0.43357(10) 0.0465(3) Uani 1 1 d . .
N11B N 0.1248(3) 0.8020(2) 0.49703(13) 0.0500(4) Uani 1 1 d . .
O12B O 0.2540(3) 0.94105(18) 0.48910(13) 0.0663(4) Uani 1 1 d . .
O13B O -0.0184(3) 0.7686(2) 0.54982(15) 0.0848(6) 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_3
C2A N1A C5A 101.38(12) .
N1A C2A N3A 110.20(13) .
N1A C2A C2A 124.69(17) 2
N3A C2A C2A 125.08(17) 2
N4A N3A C2A 109.35(12) .
N4A N3A C9A 118.53(12) .
C2A N3A C9A 132.03(13) .
C5A N4A N3A 100.98(12) .
N4A C5A N1A 118.07(13) .
N4A C5A N6A 120.56(13) .
N1A C5A N6A 121.33(13) .
O8A N6A O7A 125.07(14) .
O8A N6A C5A 117.27(13) .
O7A N6A C5A 117.64(14) .
O10A C9A N3A 111.99(12) .
O10A C9A H9A1 109.2 .
N3A C9A H9A1 109.2 .
O10A C9A H9A2 109.2 .
N3A C9A H9A2 109.2 .
H9A1 C9A H9A2 107.9 .
C9A O10A N11A 113.95(12) .
O12A N11A O13A 130.50(17) .
O12A N11A O10A 117.63(13) .
O13A N11A O10A 111.85(15) .
C2B N1B C5B 101.09(12) .
N1B C2B N3B 110.87(13) .
N1B C2B C2B 125.13(17) 2_666
N3B C2B C2B 123.99(17) 2_666
C2B N3B N4B 109.14(12) .
C2B N3B C9B 130.71(13) .
N4B N3B C9B 120.01(13) .
C5B N4B N3B 101.02(12) .
N4B C5B N1B 117.87(14) .
N4B C5B N6B 121.33(14) .
N1B C5B N6B 120.79(14) .
O8B N6B O7B 125.23(15) .
O8B N6B C5B 116.82(14) .
O7B N6B C5B 117.94(14) .
O10B C9B N3B 106.40(13) .
O10B C9B H9B1 110.4 .
N3B C9B H9B1 110.4 .
O10B C9B H9B2 110.4 .
N3B C9B H9B2 110.4 .
H9B1 C9B H9B2 108.6 .
N11B O10B C9B 112.90(13) .
O13B N11B O12B 129.63(18) .
O13B N11B O10B 112.23(16) .
O12B N11B O10B 118.11(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1A C2A 1.3222(19) .
N1A C5A 1.3334(19) .
C2A N3A 1.3608(19) .
C2A C2A 1.461(3) 2
N3A N4A 1.3542(17) .
N3A C9A 1.4635(19) .
N4A C5A 1.310(2) .
C5A N6A 1.4556(18) .
N6A O8A 1.2100(19) .
N6A O7A 1.2222(18) .
C9A O10A 1.4168(19) .
C9A H9A1 0.9700 .
C9A H9A2 0.9700 .
O10A N11A 1.4301(19) .
N11A O12A 1.1925(19) .
N11A O13A 1.1958(19) .
N1B C2B 1.320(2) .
N1B C5B 1.340(2) .
C2B N3B 1.356(2) .
C2B C2B 1.455(3) 2_666
N3B N4B 1.3584(17) .
N3B C9B 1.452(2) .
N4B C5B 1.313(2) .
C5B N6B 1.458(2) .
N6B O8B 1.2130(19) .
N6B O7B 1.2150(18) .
C9B O10B 1.432(2) .
C9B H9B1 0.9700 .
C9B H9B2 0.9700 .
O10B N11B 1.420(2) .
N11B O13B 1.185(2) .
N11B O12B 1.188(2) .
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
C9A H9A2 N1A 0.97 2.31 3.039(2) 131.0 2
C9A H9A2 O8B 0.97 2.59 3.208(2) 121.4 2_655
C9B H9B1 O12B 0.97 2.56 3.529(2) 176.5 2_676
C9B H9B2 O7A 0.97 2.54 3.455(2) 156.5 .
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
C5A N1A C2A N3A -1.27(16) . .
C5A N1A C2A C2A 176.41(18) . 2
N1A C2A N3A N4A 1.45(16) . .
C2A C2A N3A N4A -176.22(17) 2 .
N1A C2A N3A C9A 177.84(14) . .
C2A C2A N3A C9A 0.2(3) 2 .
C2A N3A N4A C5A -0.90(15) . .
C9A N3A N4A C5A -177.84(12) . .
N3A N4A C5A N1A 0.09(17) . .
N3A N4A C5A N6A 177.89(12) . .
C2A N1A C5A N4A 0.75(18) . .
C2A N1A C5A N6A -177.03(13) . .
N4A C5A N6A O8A -172.24(15) . .
N1A C5A N6A O8A 5.5(2) . .
N4A C5A N6A O7A 6.2(2) . .
N1A C5A N6A O7A -176.10(14) . .
N4A N3A C9A O10A -64.98(17) . .
C2A N3A C9A O10A 118.91(17) . .
N3A C9A O10A N11A -79.64(15) . .
C9A O10A N11A O12A 13.33(19) . .
C9A O10A N11A O13A -168.05(13) . .
C5B N1B C2B N3B -0.50(17) . .
C5B N1B C2B C2B 178.59(19) . 2_666
N1B C2B N3B N4B 0.82(18) . .
C2B C2B N3B N4B -178.28(18) 2_666 .
N1B C2B N3B C9B -174.93(16) . .
C2B C2B N3B C9B 6.0(3) 2_666 .
C2B N3B N4B C5B -0.72(16) . .
C9B N3B N4B C5B 175.56(14) . .
N3B N4B C5B N1B 0.45(18) . .
N3B N4B C5B N6B -178.33(14) . .
C2B N1B C5B N4B 0.02(19) . .
C2B N1B C5B N6B 178.81(14) . .
N4B C5B N6B O8B -175.82(16) . .
N1B C5B N6B O8B 5.4(2) . .
N4B C5B N6B O7B 5.0(2) . .
N1B C5B N6B O7B -173.73(15) . .
C2B N3B C9B O10B -76.4(2) . .
N4B N3B C9B O10B 108.28(15) . .
N3B C9B O10B N11B 143.45(13) . .
C9B O10B N11B O13B -168.29(17) . .
C9B O10B N11B O12B 13.5(2) . .
