#------------------------------------------------------------------------------
#$Date: 2023-09-02 05:06:40 +0300 (Sat, 02 Sep 2023) $
#$Revision: 285966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/30/07/2300710.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2300710
loop_
_publ_author_name
'Wang, Zhiqiang'
'Xu, Jinjiang'
'Zhao, Zhi'
'Zhang, Zhenqi'
'Tong, Yi'
_publ_section_title
;
 A novel energetic cocrystal of DATNBI/TNT with low sensitivity and an
 unexpected polymorphic transition
;
_journal_coeditor_code           JO5082SUP1
_journal_issue                   5
_journal_name_full               'Journal of Applied Crystallography'
_journal_paper_doi               10.1107/S160057672300729X
_journal_volume                  56
_journal_year                    2023
_chemical_formula_moiety         '2(C7 H5 N3 O6), C6 H4 N10 O8'
_chemical_formula_sum            'C20 H14 N16 O20'
_chemical_formula_weight         798.47
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                84.728(4)
_cell_angle_beta                 84.780(4)
_cell_angle_gamma                86.014(4)
_cell_formula_units_Z            1
_cell_length_a                   4.9325(12)
_cell_length_b                   6.8773(16)
_cell_length_c                   22.462(5)
_cell_measurement_reflns_used    957
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.79
_cell_measurement_theta_min      2.74
_cell_volume                     754.2(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3708
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         0.914
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6159
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0634 before and 0.0355 after correction.
The Ratio of minimum to maximum transmission is 0.8260.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_description       block
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0782
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2205
_refine_ls_wR_factor_ref         0.2874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1421
_reflns_number_total             2584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5082sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        754.1(3)
_cod_database_code               2300710
_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_max   0.992
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6)
2.c Idealised Me refined as rotating group:
 C7(H7B,H7C,H7A)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4867(12) 0.3804(8) 0.7184(2) 0.0880(16) Uani 1 1 d . . . . .
O2 O 0.8664(10) 0.2163(7) 0.70182(19) 0.0767(14) Uani 1 1 d . . . . .
O3 O 1.0615(10) -0.3814(7) 0.8234(2) 0.0757(13) Uani 1 1 d . . . . .
O4 O 0.7044(11) -0.5283(7) 0.8573(3) 0.0976(18) Uani 1 1 d . . . . .
O5 O -0.0737(9) -0.0016(8) 0.93521(19) 0.0743(14) Uani 1 1 d . . . . .
O6 O 0.1471(10) 0.2561(7) 0.9400(2) 0.0785(15) Uani 1 1 d . . . . .
N1 N 0.6507(11) 0.2451(8) 0.7302(2) 0.0583(13) Uani 1 1 d . . . . .
N2 N 0.8186(11) -0.3812(7) 0.8398(2) 0.0548(13) Uani 1 1 d . . . . .
N3 N 0.1171(9) 0.1013(8) 0.92007(19) 0.0516(12) Uani 1 1 d . . . . .
C1 C 0.5806(11) 0.1098(8) 0.7824(2) 0.0442(13) Uani 1 1 d . . . . .
C2 C 0.7260(11) -0.0683(8) 0.7878(2) 0.0450(13) Uani 1 1 d . . . . .
H2 H 0.8649 -0.1024 0.7591 0.054 Uiso 1 1 calc R . . . .
C3 C 0.6575(11) -0.1944(7) 0.8376(2) 0.0457(13) Uani 1 1 d . . . . .
C4 C 0.4605(11) -0.1510(8) 0.8839(2) 0.0444(13) Uani 1 1 d . . . . .
C5 C 0.3250(10) 0.0327(7) 0.8743(2) 0.0395(12) Uani 1 1 d . . . . .
C6 C 0.3765(11) 0.1629(8) 0.8248(2) 0.0443(13) Uani 1 1 d . . . . .
H6 H 0.2769 0.2824 0.8202 0.053 Uiso 1 1 calc R . . . .
C7 C 0.4122(14) -0.2809(9) 0.9409(3) 0.0645(17) Uani 1 1 d . . . . .
H7B H 0.3574 -0.2019 0.9735 0.097 Uiso 1 1 calc GR . . . .
H7C H 0.5772 -0.3572 0.9490 0.097 Uiso 1 1 calc GR . . . .
H7A H 0.2710 -0.3667 0.9365 0.097 Uiso 1 1 calc GR . . . .
O7 O -0.0013(9) 0.6714(7) 0.67500(18) 0.0662(13) Uani 1 1 d . . . . .
O8 O 0.3340(9) 0.8331(7) 0.69490(19) 0.0715(14) Uani 1 1 d . . . . .
O9 O 0.5305(9) 1.1062(6) 0.6074(2) 0.0714(13) Uani 1 1 d . . . . .
O10 O 0.9196(9) 1.0006(6) 0.5666(2) 0.0652(12) Uani 1 1 d . . . . .
N4 N 0.6441(9) 0.7203(6) 0.52182(18) 0.0438(11) Uani 1 1 d . . . . .
N5 N 0.6822(10) 0.9839(7) 0.58313(19) 0.0483(11) Uani 1 1 d . . . . .
N6 N 0.2219(10) 0.7383(7) 0.66226(19) 0.0487(12) Uani 1 1 d . . . . .
N7 N 0.3104(8) 0.5550(6) 0.57257(17) 0.0385(10) Uani 1 1 d . . . . .
N8 N 0.0949(8) 0.4306(7) 0.58389(19) 0.0471(12) Uani 1 1 d . . . . .
H8A H 0.1411 0.3212 0.5683 0.057 Uiso 1 1 d GR . . . .
H8B H 0.0572 0.4061 0.6222 0.057 Uiso 1 1 d GR . . . .
C8 C 0.3609(10) 0.7059(7) 0.6053(2) 0.0405(12) Uani 1 1 d . . . . .
C9 C 0.5637(10) 0.8037(7) 0.5724(2) 0.0386(12) Uani 1 1 d . . . . .
C10 C 0.4885(10) 0.5670(8) 0.5228(2) 0.0415(12) 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
_geom_angle_publ_flag
O1 N1 C1 117.6(5) . . ?
O2 N1 O1 124.3(5) . . ?
O2 N1 C1 118.2(6) . . ?
O3 N2 C3 118.4(5) . . ?
O4 N2 O3 123.1(5) . . ?
O4 N2 C3 118.4(5) . . ?
O5 N3 C5 117.5(5) . . ?
O6 N3 O5 124.8(5) . . ?
O6 N3 C5 117.8(4) . . ?
C2 C1 N1 118.1(5) . . ?
C6 C1 N1 119.9(5) . . ?
C6 C1 C2 121.9(5) . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.4(5) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 N2 114.2(5) . . ?
C2 C3 C4 124.8(5) . . ?
C4 C3 N2 121.0(5) . . ?
C3 C4 C5 113.4(5) . . ?
C3 C4 C7 123.8(6) . . ?
C5 C4 C7 122.7(5) . . ?
C4 C5 N3 119.6(5) . . ?
C6 C5 N3 115.5(5) . . ?
C6 C5 C4 124.8(5) . . ?
C1 C6 C5 117.6(5) . . ?
C1 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H7B C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
C9 N4 C10 105.0(4) . . ?
O9 N5 C9 116.8(5) . . ?
O10 N5 O9 125.8(5) . . ?
O10 N5 C9 117.4(5) . . ?
O7 N6 C8 118.4(4) . . ?
O8 N6 O7 124.4(4) . . ?
O8 N6 C8 117.2(4) . . ?
C8 N7 N8 126.9(4) . . ?
C10 N7 N8 126.4(4) . . ?
C10 N7 C8 106.2(4) . . ?
N7 N8 H8A 109.4 . . ?
N7 N8 H8B 110.5 . . ?
H8A N8 H8B 108.6 . . ?
N7 C8 N6 123.3(4) . . ?
C9 C8 N6 130.8(4) . . ?
C9 C8 N7 105.8(4) . . ?
N4 C9 N5 118.8(4) . . ?
N4 C9 C8 111.5(4) . . ?
C8 C9 N5 129.5(4) . . ?
N4 C10 N7 111.4(4) . . ?
N4 C10 C10 123.9(5) . 2_666 ?
N7 C10 C10 124.7(5) . 2_666 ?
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
O1 N1 1.216(7) . ?
O2 N1 1.204(6) . ?
O3 N2 1.221(6) . ?
O4 N2 1.208(6) . ?
O5 N3 1.221(5) . ?
O6 N3 1.216(6) . ?
N1 C1 1.460(7) . ?
N2 C3 1.462(7) . ?
N3 C5 1.471(6) . ?
C1 C2 1.377(8) . ?
C1 C6 1.376(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(8) . ?
C3 C4 1.396(7) . ?
C4 C5 1.396(8) . ?
C4 C7 1.502(8) . ?
C5 C6 1.378(7) . ?
C6 H6 0.9300 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 H7A 0.9600 . ?
O7 N6 1.222(6) . ?
O8 N6 1.216(6) . ?
O9 N5 1.220(6) . ?
O10 N5 1.206(6) . ?
N4 C9 1.334(6) . ?
N4 C10 1.344(6) . ?
N5 C9 1.456(6) . ?
N6 C8 1.425(6) . ?
N7 N8 1.401(5) . ?
N7 C8 1.374(6) . ?
N7 C10 1.358(6) . ?
N8 H8A 0.8664 . ?
N8 H8B 0.8666 . ?
C8 C9 1.366(6) . ?
C10 C10 1.431(10) 2_666 ?

_cod_database_fobs_code 2300710
