#------------------------------------------------------------------------------
#$Date: 2023-11-06 10:00:41 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287380 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/27/7062772.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_7062772
loop_
_publ_author_name
'Li, Qiaoli'
'Li, Shenshen'
'Xiao, Jijun'
_publ_section_title
;
 Exploring high-energy and low-sensitivity energetic compounds based on
 experiments and DFT studies
;
_journal_issue                   42
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19523
_journal_page_last               19528
_journal_paper_doi               10.1039/D3NJ03514J
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         '0.5(H4 O2), C4 N14, 2(H5 N2)'
_chemical_formula_sum            'C4 H12 N18 O'
_chemical_formula_weight         328.32
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-08-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.365(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.1895(12)
_cell_length_b                   3.6111(2)
_cell_length_c                   16.0327(9)
_cell_measurement_reflns_used    805
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.612
_cell_measurement_theta_min      3.819
_cell_volume                     1340.26(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4691
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.707
_diffrn_reflns_theta_min         3.819
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_T_max  0.8643
_exptl_absorpt_correction_T_min  0.6362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1552 before and 0.0691 after correction.
The Ratio of minimum to maximum transmission is 0.7361.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0633
_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)+(0.1136P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                920
_reflns_number_total             1238
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj03514j2.cif
_cod_data_source_block           cu_20220826_zh_nlg_lcj_jingyan
_cod_depositor_comments          'Adding full bibliography for 7062772.cif.'
_cod_database_code               7062772
_shelx_shelxl_version_number     2018/3
_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   0.895
_shelx_estimated_absorpt_t_min   0.867
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5)
3.a Free rotating group:
 O1(H1A,H1B)
3.b Idealised Me refined as rotating group:
 N9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.500000 1.2104(7) 0.250000 0.0287(7) Uani 1 2 d GS T P . .
H1A H 0.530375 1.323209 0.271911 0.043 Uiso 0.5 1 d G U P . .
H1B H 0.480986 1.381723 0.221930 0.043 Uiso 0.5 1 d G U P . .
N1 N 0.50391(9) 0.4929(6) 0.46118(15) 0.0233(6) Uani 1 1 d . . . . .
C1 C 0.55780(11) 0.6266(7) 0.44108(17) 0.0218(6) Uani 1 1 d . . . . .
C2 C 0.63975(12) 0.8466(7) 0.43855(19) 0.0272(7) Uani 1 1 d . . . . .
N2 N 0.59958(10) 0.7808(6) 0.49328(15) 0.0251(6) Uani 1 1 d . . . . .
N3 N 0.57175(10) 0.6037(6) 0.36197(15) 0.0265(6) Uani 1 1 d . . . . .
N4 N 0.62608(10) 0.7469(6) 0.35932(16) 0.0298(6) Uani 1 1 d . . . . .
N5 N 0.69299(11) 1.0076(7) 0.46474(18) 0.0351(7) Uani 1 1 d . . . . .
N6 N 0.72492(12) 1.0692(7) 0.4063(2) 0.0411(8) Uani 1 1 d . . . . .
N7 N 0.75814(14) 1.1399(10) 0.3590(2) 0.0563(9) Uani 1 1 d . . . . .
N8 N 0.62821(11) 1.1754(7) 0.19248(19) 0.0298(6) Uani 1 1 d . . . . .
H8A H 0.6581(17) 1.129(10) 0.164(2) 0.036 Uiso 1 1 d . U . . .
H8B H 0.6316(16) 1.117(10) 0.245(3) 0.036 Uiso 1 1 d . U . . .
N9 N 0.58620(10) 0.9209(6) 0.15533(16) 0.0279(6) Uani 1 1 d . . . . .
H9A H 0.581887 0.963026 0.099347 0.033 Uiso 1 1 calc R U . . .
H9B H 0.551730 0.954818 0.178588 0.033 Uiso 1 1 calc R U . . .
H9C H 0.598482 0.684333 0.164604 0.033 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
H1A O1 H1A 124.1 . 2_655 ?
H1A O1 H1B 104.5 2_655 2_655 ?
H1A O1 H1B 23.6 . 2_655 ?
H1A O1 H1B 104.5 . . ?
H1B O1 H1A 23.6 . 2_655 ?
H1B O1 H1B 89.3 . 2_655 ?
N1 N1 C1 113.2(3) 5_666 . ?
N2 C1 N1 127.9(3) . . ?
N3 C1 N1 118.0(2) . . ?
N3 C1 N2 114.0(2) . . ?
N2 C2 N4 116.0(2) . . ?
N2 C2 N5 120.7(3) . . ?
N4 C2 N5 123.3(3) . . ?
C2 N2 C1 99.6(2) . . ?
C1 N3 N4 106.4(2) . . ?
C2 N4 N3 103.9(2) . . ?
N6 N5 C2 113.5(3) . . ?
N7 N6 N5 172.9(3) . . ?
H8A N8 H8B 115(3) . . ?
N9 N8 H8A 102(2) . . ?
N9 N8 H8B 105(2) . . ?
N8 N9 H9A 109.5 . . ?
N8 N9 H9B 109.5 . . ?
N8 N9 H9C 109.5 . . ?
H9A N9 H9B 109.5 . . ?
H9A N9 H9C 109.5 . . ?
H9B N9 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
O1 H1A 0.8698 . ?
O1 H1A 0.87(6) 2_655 ?
O1 H1B 0.87(10) 2_655 ?
O1 H1B 0.8698 . ?
N1 N1 1.269(5) 5_666 ?
N1 C1 1.395(3) . ?
C1 N2 1.362(3) . ?
C1 N3 1.330(4) . ?
C2 N2 1.338(4) . ?
C2 N4 1.340(4) . ?
C2 N5 1.406(4) . ?
N3 N4 1.365(3) . ?
N5 N6 1.248(4) . ?
N6 N7 1.141(4) . ?
N8 H8A 0.86(4) . ?
N8 H8B 0.87(4) . ?
N8 N9 1.442(3) . ?
N9 H9A 0.9100 . ?
N9 H9B 0.9100 . ?
N9 H9C 0.9100 . ?
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
N1 N1 C1 N2 -3.6(4) 5_666 . . . ?
N1 N1 C1 N3 176.1(3) 5_666 . . . ?
N1 C1 N2 C2 179.4(2) . . . . ?
N1 C1 N3 N4 -179.3(2) . . . . ?
C1 N3 N4 C2 -0.4(3) . . . . ?
N2 C1 N3 N4 0.4(3) . . . . ?
N2 C2 N4 N3 0.3(3) . . . . ?
N2 C2 N5 N6 -176.6(3) . . . . ?
N3 C1 N2 C2 -0.2(3) . . . . ?
N4 C2 N2 C1 -0.1(3) . . . . ?
N4 C2 N5 N6 4.1(4) . . . . ?
N5 C2 N2 C1 -179.4(2) . . . . ?
N5 C2 N4 N3 179.6(2) . . . . ?
