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#$Date: 2022-04-07 01:33:17 +0300 (Thu, 07 Apr 2022) $
#$Revision: 274404 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/47/7244719.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_7244719
loop_
_publ_author_name
'Qiao, Shen'
'Wang, Jianhua'
'Yu, Yanwu'
'Liu, Yucun'
'Yang, Zongwei'
'Li, Hongzhen'
_publ_section_title
;
 Two novel TNB energetic cocrystals with low melting point: a potential
 strategy to construct melt cast explosive carriers
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00025C
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_sum            'C9 H6 N8 O10'
_chemical_formula_weight         386.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-12-01 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7852(17)
_cell_length_b                   11.054(3)
_cell_length_c                   20.043(5)
_cell_measurement_reflns_used    1715
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      42.761
_cell_measurement_theta_min      5.487
_cell_volume                     1503.3(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10367
_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         25.496
_diffrn_reflns_theta_min         2.032
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 623 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.2(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0399
_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)+(0.0566P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1144
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1819
_reflns_number_total             2796
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00025c2.cif
_cod_data_source_block           mo_dm17411_0m
_cod_original_cell_volume        1503.4(6)
_cod_database_code               7244719
_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   0.969
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6411(5) 0.1360(4) 0.1756(2) 0.0609(10) Uani 1 1 d . . . . .
N2 N 0.2895(6) 0.0539(4) 0.38448(19) 0.0588(10) Uani 1 1 d . . . . .
N3 N 0.0419(6) 0.3627(4) 0.2289(2) 0.0620(11) Uani 1 1 d . . . . .
N4 N 0.1953(5) 1.0447(3) 0.08781(18) 0.0572(10) Uani 1 1 d . . . . .
N5 N 0.0184(6) 0.8807(4) 0.0555(2) 0.0607(11) Uani 1 1 d . . . . .
N6 N -0.0745(5) 0.9827(4) 0.03627(18) 0.0538(10) Uani 1 1 d . . . . .
N7 N -0.0191(6) 1.2019(4) 0.0438(2) 0.0599(10) Uani 1 1 d . . . . .
N8 N 0.3222(6) 0.8446(4) 0.1121(2) 0.0688(11) Uani 1 1 d . . . . .
O1 O 0.6403(5) 0.1869(4) 0.12201(19) 0.0846(12) Uani 1 1 d . . . . .
O2 O 0.7672(5) 0.0644(4) 0.19275(19) 0.0907(13) Uani 1 1 d . . . . .
O3 O 0.4013(5) -0.0309(3) 0.39349(18) 0.0803(11) Uani 1 1 d . . . . .
O4 O 0.1683(6) 0.0884(3) 0.42465(17) 0.0813(11) Uani 1 1 d . . . . .
O5 O -0.1177(5) 0.3598(4) 0.2577(2) 0.0877(12) Uani 1 1 d . . . . .
O6 O 0.0886(5) 0.4371(3) 0.18731(19) 0.0771(11) Uani 1 1 d . . . . .
O7 O -0.1188(6) 1.2228(3) -0.0049(2) 0.0777(11) Uani 1 1 d . . . . .
O8 O 0.0398(6) 1.2775(3) 0.0839(2) 0.0840(12) Uani 1 1 d . . . . .
O9 O 0.4672(6) 0.8903(4) 0.1395(2) 0.0934(13) Uani 1 1 d . . . . .
O10 O 0.2921(6) 0.7362(4) 0.1084(2) 0.0925(12) Uani 1 1 d . . . . .
C1 C 0.4749(6) 0.1606(4) 0.2215(2) 0.0474(10) Uani 1 1 d . . . . .
C2 C 0.4624(6) 0.0949(4) 0.2793(2) 0.0478(10) Uani 1 1 d . . . . .
H2 H 0.5558 0.0366 0.2902 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3044(6) 0.1196(4) 0.3205(2) 0.0455(10) Uani 1 1 d . . . . .
C4 C 0.1648(6) 0.2045(4) 0.3053(2) 0.0491(11) Uani 1 1 d . . . . .
H4 H 0.0581 0.2185 0.3334 0.059 Uiso 1 1 calc R U . . .
C5 C 0.1878(6) 0.2685(4) 0.2468(2) 0.0490(11) Uani 1 1 d . . . . .
C6 C 0.3423(6) 0.2484(4) 0.2038(2) 0.0512(11) Uani 1 1 d . . . . .
H6 H 0.3561 0.2923 0.1645 0.061 Uiso 1 1 calc R U . . .
C7 C 0.0353(7) 1.0777(4) 0.0560(2) 0.0514(11) Uani 1 1 d . . . . .
C8 C 0.1769(7) 0.9251(4) 0.0852(2) 0.0543(11) Uani 1 1 d . . . . .
C9 C -0.2648(8) 0.9758(5) 0.0012(3) 0.0724(14) Uani 1 1 d . . . . .
H9A H -0.2485 1.0029 -0.0439 0.109 Uiso 1 1 calc R U . . .
H9B H -0.3592 1.0263 0.0235 0.109 Uiso 1 1 calc R U . . .
H9C H -0.3107 0.8936 0.0012 0.109 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 123.8(4) . . ?
O1 N1 C1 117.5(4) . . ?
O2 N1 C1 118.7(4) . . ?
O4 N2 O3 124.5(4) . . ?
O4 N2 C3 117.9(4) . . ?
O3 N2 C3 117.6(4) . . ?
O6 N3 O5 124.8(4) . . ?
O6 N3 C5 117.9(4) . . ?
O5 N3 C5 117.3(5) . . ?
C7 N4 C8 100.4(4) . . ?
C8 N5 N6 101.5(4) . . ?
N5 N6 C7 108.0(3) . . ?
N5 N6 C9 120.2(4) . . ?
C7 N6 C9 131.7(4) . . ?
O7 N7 O8 125.5(4) . . ?
O7 N7 C7 117.5(4) . . ?
O8 N7 C7 117.0(4) . . ?
O10 N8 O9 124.3(5) . . ?
O10 N8 C8 118.2(4) . . ?
O9 N8 C8 117.5(4) . . ?
C6 C1 C2 123.6(4) . . ?
C6 C1 N1 118.0(4) . . ?
C2 C1 N1 118.4(4) . . ?
C1 C2 C3 116.7(4) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 122.6(4) . . ?
C4 C3 N2 118.9(4) . . ?
C2 C3 N2 118.4(4) . . ?
C3 C4 C5 117.7(4) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 122.4(4) . . ?
C6 C5 N3 118.1(4) . . ?
C4 C5 N3 119.4(4) . . ?
C1 C6 C5 116.9(4) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
N4 C7 N6 112.6(4) . . ?
N4 C7 N7 124.0(4) . . ?
N6 C7 N7 123.4(4) . . ?
N5 C8 N4 117.5(4) . . ?
N5 C8 N8 119.9(4) . . ?
N4 C8 N8 122.6(4) . . ?
N6 C9 H9A 109.5 . . ?
N6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.212(5) . ?
N1 O2 1.215(5) . ?
N1 C1 1.480(5) . ?
N2 O4 1.212(5) . ?
N2 O3 1.219(5) . ?
N2 C3 1.477(5) . ?
N3 O6 1.214(5) . ?
N3 O5 1.227(5) . ?
N3 C5 1.481(6) . ?
N4 C7 1.311(5) . ?
N4 C8 1.329(5) . ?
N5 C8 1.324(6) . ?
N5 N6 1.347(5) . ?
N6 C7 1.347(5) . ?
N6 C9 1.472(6) . ?
N7 O7 1.210(5) . ?
N7 O8 1.226(5) . ?
N7 C7 1.443(6) . ?
N8 O10 1.217(5) . ?
N8 O9 1.235(5) . ?
N8 C8 1.434(6) . ?
C1 C6 1.370(6) . ?
C1 C2 1.370(6) . ?
C2 C3 1.381(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(6) . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(6) . ?
C6 H6 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N5 N6 C7 -0.1(4) . . . . ?
C8 N5 N6 C9 -179.0(4) . . . . ?
O1 N1 C1 C6 -6.7(6) . . . . ?
O2 N1 C1 C6 175.0(4) . . . . ?
O1 N1 C1 C2 173.5(4) . . . . ?
O2 N1 C1 C2 -4.8(6) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
N1 C1 C2 C3 -179.4(4) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C1 C2 C3 N2 -177.8(4) . . . . ?
O4 N2 C3 C4 -9.1(6) . . . . ?
O3 N2 C3 C4 171.6(4) . . . . ?
O4 N2 C3 C2 169.1(4) . . . . ?
O3 N2 C3 C2 -10.2(5) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
N2 C3 C4 C5 176.9(4) . . . . ?
C3 C4 C5 C6 1.1(6) . . . . ?
C3 C4 C5 N3 -179.0(4) . . . . ?
O6 N3 C5 C6 -18.0(6) . . . . ?
O5 N3 C5 C6 162.3(4) . . . . ?
O6 N3 C5 C4 162.1(4) . . . . ?
O5 N3 C5 C4 -17.6(6) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
N1 C1 C6 C5 179.2(4) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
N3 C5 C6 C1 -179.9(4) . . . . ?
C8 N4 C7 N6 0.8(5) . . . . ?
C8 N4 C7 N7 -179.6(4) . . . . ?
N5 N6 C7 N4 -0.5(5) . . . . ?
C9 N6 C7 N4 178.3(4) . . . . ?
N5 N6 C7 N7 179.9(4) . . . . ?
C9 N6 C7 N7 -1.3(7) . . . . ?
O7 N7 C7 N4 152.1(4) . . . . ?
O8 N7 C7 N4 -27.9(6) . . . . ?
O7 N7 C7 N6 -28.3(6) . . . . ?
O8 N7 C7 N6 151.6(4) . . . . ?
N6 N5 C8 N4 0.7(5) . . . . ?
N6 N5 C8 N8 -178.4(4) . . . . ?
C7 N4 C8 N5 -0.9(5) . . . . ?
C7 N4 C8 N8 178.1(4) . . . . ?
O10 N8 C8 N5 -2.0(7) . . . . ?
O9 N8 C8 N5 -179.8(4) . . . . ?
O10 N8 C8 N4 179.0(5) . . . . ?
O9 N8 C8 N4 1.2(7) . . . . ?
