#------------------------------------------------------------------------------
#$Date: 2019-11-24 12:31:55 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237910 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/46/1554628.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_1554628
loop_
_publ_author_name
'Huang, Qi'
'Guo, Zhicheng'
'Liao, Longyu'
'Hao, Shilong'
'Nie, Fude'
'Li, Hongzhen'
_publ_section_title
;
 Customization of the molecular structure to modulate the crystal packing
 style of energetic materials
;
_journal_issue                   5
_journal_name_full               'Molecular Systems Design & Engineering'
_journal_page_first              1032
_journal_paper_doi               10.1039/C9ME00051H
_journal_volume                  4
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C8 H8 N10 O14'
_chemical_formula_weight         468.24
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-06-08 deposited with the CCDC.	2019-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0912(5)
_cell_length_b                   7.0912(5)
_cell_length_c                   34.097(4)
_cell_measurement_reflns_used    2743
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.292
_cell_measurement_theta_min      4.779
_cell_volume                     1714.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            9946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.389
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
; 
 Flack x determined using 494 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -1.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0390
_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)+(0.0528P)²+0.3367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.546
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1478
_reflns_number_total             1603
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9me00051h2.cif
_cod_data_source_block           cd16604
_cod_database_code               1554628
_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   0.966
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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
N1 N 0.4950(3) 0.4950(3) 0.0000 0.0325(7) Uani 1 2 d S T P
N2 N 0.7682(3) 0.7682(3) 0.0000 0.0429(8) Uani 1 2 d S T P
N3 N 0.6347(4) 0.9340(4) 0.05229(9) 0.0567(7) Uani 1 1 d . . .
N4 N 0.3264(3) 0.6371(3) 0.04911(7) 0.0408(6) Uani 1 1 d . . .
N5 N 0.2218(4) 0.8002(4) 0.05442(8) 0.0488(6) Uani 1 1 d . . .
N6 N -0.1530(3) 0.4015(4) 0.09007(7) 0.0457(6) Uani 1 1 d . . .
O1 O 0.6848(5) 1.0848(4) 0.03959(9) 0.0876(10) Uani 1 1 d . . .
O2 O 0.5935(5) 0.8988(4) 0.08573(7) 0.0809(9) Uani 1 1 d . . .
O3 O 0.2695(4) 0.9360(3) 0.03519(7) 0.0648(7) Uani 1 1 d . . .
O4 O 0.0925(4) 0.7921(3) 0.07727(7) 0.0664(7) Uani 1 1 d . . .
O5 O -0.0689(3) 0.4382(3) 0.05405(6) 0.0432(5) Uani 1 1 d . . .
O6 O -0.0753(4) 0.3004(4) 0.11217(8) 0.0765(8) Uani 1 1 d . . .
O7 O -0.3006(4) 0.4812(4) 0.09356(8) 0.0771(8) Uani 1 1 d . . .
C1 C 0.4829(4) 0.6410(4) 0.02424(7) 0.0327(6) Uani 1 1 d . . .
C2 C 0.6255(4) 0.7749(4) 0.02421(8) 0.0380(6) Uani 1 1 d . . .
C3 C 0.2691(4) 0.4652(4) 0.06940(8) 0.0375(6) Uani 1 1 d . . .
H3A H 0.2279 0.4986 0.0956 0.045 Uiso 1 1 calc R U .
H3B H 0.3785 0.3841 0.0720 0.045 Uiso 1 1 calc R U .
C4 C 0.1151(4) 0.3552(4) 0.04998(10) 0.0493(7) Uani 1 1 d . . .
H4A H 0.1441 0.3434 0.0223 0.059 Uiso 1 1 calc R U .
H4B H 0.1125 0.2292 0.0611 0.059 Uiso 1 1 calc R U .
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
C1 N1 C1 119.2(3) 7
C2 N2 C2 117.1(3) 7
O2 N3 O1 126.5(3) .
O2 N3 C2 116.4(3) .
O1 N3 C2 117.1(3) .
N5 N4 C1 119.2(2) .
N5 N4 C3 119.1(2) .
C1 N4 C3 121.7(2) .
O4 N5 O3 126.8(3) .
O4 N5 N4 116.9(3) .
O3 N5 N4 116.3(2) .
O6 N6 O7 129.3(3) .
O6 N6 O5 118.6(3) .
O7 N6 O5 112.0(3) .
N6 O5 C4 113.5(2) .
N1 C1 C2 119.1(3) .
N1 C1 N4 114.5(2) .
C2 C1 N4 126.4(2) .
N2 C2 C1 122.7(3) .
N2 C2 N3 113.7(3) .
C1 C2 N3 123.6(3) .
N4 C3 C4 115.4(2) .
N4 C3 H3A 108.4 .
C4 C3 H3A 108.4 .
N4 C3 H3B 108.4 .
C4 C3 H3B 108.4 .
H3A C3 H3B 107.5 .
O5 C4 C3 114.0(2) .
O5 C4 H4A 108.8 .
C3 C4 H4A 108.8 .
O5 C4 H4B 108.8 .
C3 C4 H4B 108.8 .
H4A C4 H4B 107.7 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.327(3) .
N1 C1 1.328(3) 7
N2 C2 1.307(3) .
N2 C2 1.307(3) 7
N3 O2 1.203(4) .
N3 O1 1.207(4) .
N3 C2 1.481(4) .
N4 N5 1.385(3) .
N4 C1 1.397(3) .
N4 C3 1.460(3) .
N5 O4 1.204(3) .
N5 O3 1.214(3) .
N6 O6 1.177(3) .
N6 O7 1.195(4) .
N6 O5 1.390(3) .
O5 C4 1.438(4) .
C1 C2 1.387(4) .
C3 C4 1.496(4) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
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
C4 H4B O3 0.97 2.52 3.207(4) 128.0 1_545
C4 H4A O3 0.97 2.51 3.227(4) 130.8 7_455
C3 H3B O7 0.97 2.49 3.163(4) 126.5 1_655
C3 H3B O6 0.97 2.62 3.195(4) 118.4 6
C3 H3A O2 0.97 2.63 3.598(4) 175.6 6_465
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
C1 N4 N5 O4 -177.2(3) .
C3 N4 N5 O4 3.3(4) .
C1 N4 N5 O3 3.4(4) .
C3 N4 N5 O3 -176.0(3) .
O6 N6 O5 C4 -4.6(4) .
O7 N6 O5 C4 175.8(3) .
C1 N1 C1 C2 -1.45(17) 7
C1 N1 C1 N4 -178.5(2) 7
N5 N4 C1 N1 -135.3(2) .
C3 N4 C1 N1 44.2(3) .
N5 N4 C1 C2 48.0(4) .
C3 N4 C1 C2 -132.6(3) .
C2 N2 C2 C1 -1.54(19) 7
C2 N2 C2 N3 176.3(3) 7
N1 C1 C2 N2 3.1(4) .
N4 C1 C2 N2 179.7(2) .
N1 C1 C2 N3 -174.5(2) .
N4 C1 C2 N3 2.1(4) .
O2 N3 C2 N2 -137.1(3) .
O1 N3 C2 N2 42.0(4) .
O2 N3 C2 C1 40.8(4) .
O1 N3 C2 C1 -140.1(3) .
N5 N4 C3 C4 82.3(3) .
C1 N4 C3 C4 -97.2(3) .
N6 O5 C4 C3 -80.2(3) .
N4 C3 C4 O5 -74.7(3) .
