#------------------------------------------------------------------------------
#$Date: 2024-10-06 07:35:44 +0200 (Sun 06 de Oct de 2024) $
#$Revision: 295120 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/35/7133575.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_7133575
loop_
_publ_author_name
'Yang, Pengju'
'Zheng, Xiaoxiao'
'Zhang, Guojie'
'Lei, Caijing'
'Cheng, Guangbin'
'Yang, Hongwei'
_publ_section_title
;
 Construction of heterocycle-triazolotriazine framework energetic
 compounds: towards novel high-performance explosives.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10588
_journal_page_last               10591
_journal_paper_doi               10.1039/d4cc03260h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         '2(H2 O), C6 H3 N11 O4'
_chemical_formula_sum            'C6 H7 N11 O6'
_chemical_formula_weight         329.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-18 deposited with the CCDC.	2024-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.827(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.966(2)
_cell_length_b                   13.360(3)
_cell_length_c                   18.602(4)
_cell_measurement_reflns_used    1990
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.601
_cell_measurement_theta_min      2.24
_cell_volume                     2468.0(9)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_av_unetI/netI     0.0877
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19352
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_min         2.197
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0759 before and 0.0668 after correction. The Ratio of minimum to maximum transmission is 0.8884. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0601
_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)+(0.0695P)²+0.0485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2440
_reflns_number_total             4448
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03260h2.cif
_cod_data_source_block           mo_2021771_0m
_cod_depositor_comments
'Adding full bibliography for 7133573--7133575.cif.'
_cod_original_cell_volume        2467.9(9)
_cod_database_code               7133575
_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   0.997
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B), O9(H9A,H9B), O10(H10A,H10B), O8(H8A,H8B)
2.b X=CH2 refined with riding coordinates:
 N22(H22A,H22B), N6(H6A,H6B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O3 O 0.5380(3) 0.8309(2) 0.46456(15) 0.0404(8) Uani 1 1 d . . . . .
H3A H 0.592839 0.881424 0.463867 0.061 Uiso 1 1 d G . . . .
H3B H 0.490400 0.826657 0.423271 0.061 Uiso 1 1 d G . . . .
O9 O 0.8451(3) -0.1260(2) 0.60350(15) 0.0380(7) Uani 1 1 d . . . . .
H9A H 0.916096 -0.129191 0.633978 0.057 Uiso 1 1 d G . . . .
H9B H 0.824088 -0.185802 0.587816 0.057 Uiso 1 1 d G . . . .
O12 O 0.0361(3) 0.1577(2) 0.14495(15) 0.0402(8) Uani 1 1 d . . . . .
O4 O 0.7998(3) 0.3727(2) 0.58067(15) 0.0402(8) Uani 1 1 d . . . . .
O11 O 0.1428(3) 0.2979(2) 0.16198(15) 0.0395(7) Uani 1 1 d . . . . .
O10 O 0.5290(3) 0.4415(2) 0.34133(16) 0.0419(8) Uani 1 1 d . . . . .
H10A H 0.568278 0.432737 0.384401 0.063 Uiso 1 1 d G . . . .
H10B H 0.480966 0.495967 0.340506 0.063 Uiso 1 1 d G . . . .
O6 O 0.9240(3) 0.2931(2) 0.45761(15) 0.0419(8) Uani 1 1 d . . . . .
O5 O 0.6550(3) 0.3734(2) 0.48626(16) 0.0430(8) Uani 1 1 d . . . . .
O2 O 1.4196(3) 0.4068(2) 0.80002(15) 0.0399(7) Uani 1 1 d . . . . .
O7 O 0.7704(3) 0.2782(2) 0.36822(16) 0.0432(8) Uani 1 1 d . . . . .
N18 N 0.4070(3) 0.1604(2) 0.30816(16) 0.0286(8) Uani 1 1 d . . . . .
N4 N 1.0872(3) 0.5336(2) 0.69560(16) 0.0297(8) Uani 1 1 d . . . . .
O1 O 1.4578(3) 0.5462(2) 0.85782(17) 0.0525(9) Uani 1 1 d . . . . .
N16 N 0.5167(3) 0.1916(2) 0.35071(17) 0.0301(8) Uani 1 1 d . . . . .
N20 N 0.2061(3) 0.0641(2) 0.23402(17) 0.0318(8) Uani 1 1 d . . . . .
N5 N 0.9966(3) 0.5033(2) 0.64103(17) 0.0323(8) Uani 1 1 d . . . . .
N17 N 0.4856(3) 0.0210(2) 0.35905(17) 0.0325(8) Uani 1 1 d . . . . .
N9 N 0.6619(4) 0.6653(3) 0.50881(19) 0.0377(9) Uani 1 1 d . . . . .
N8 N 0.7571(3) 0.6811(3) 0.56149(17) 0.0349(9) Uani 1 1 d . . . . .
N21 N 0.1262(4) 0.2081(3) 0.17531(18) 0.0354(9) Uani 1 1 d . . . . .
N22 N 0.3494(3) 0.3164(2) 0.26333(17) 0.0337(8) Uani 1 1 d . . . . .
H22A H 0.418318 0.341295 0.290227 0.040 Uiso 1 1 calc R . . . .
H22B H 0.297260 0.356132 0.235537 0.040 Uiso 1 1 calc R . . . .
N7 N 0.9471(3) 0.6602(3) 0.68155(17) 0.0344(9) Uani 1 1 d . . . . .
N1 N 1.3896(3) 0.4949(3) 0.81376(18) 0.0343(9) Uani 1 1 d . . . . .
N15 N 0.6902(3) 0.0129(3) 0.47237(18) 0.0357(9) Uani 1 1 d . . . . .
N12 N 0.8307(4) 0.2490(3) 0.42422(18) 0.0357(9) Uani 1 1 d . . . . .
N6 N 1.2149(3) 0.3901(3) 0.69780(18) 0.0364(9) Uani 1 1 d . . . . .
H6A H 1.158467 0.365793 0.663239 0.044 Uiso 1 1 calc R . . . .
H6B H 1.284296 0.354199 0.715089 0.044 Uiso 1 1 calc R . . . .
N10 N 0.6403(3) 0.5713(3) 0.49038(18) 0.0354(9) Uani 1 1 d . . . . .
N3 N 1.1339(3) 0.6762(3) 0.77149(18) 0.0347(8) Uani 1 1 d . . . . .
N2 N 1.2402(3) 0.6278(3) 0.79878(17) 0.0346(9) Uani 1 1 d . . . . .
N19 N 0.2870(3) 0.0091(2) 0.27636(17) 0.0329(8) Uani 1 1 d . . . . .
N11 N 0.7288(4) 0.4153(3) 0.53372(19) 0.0359(9) Uani 1 1 d . . . . .
N13 N 0.8668(4) 0.1105(3) 0.50442(18) 0.0382(9) Uani 1 1 d . . . . .
N14 N 0.8018(4) 0.0265(3) 0.5139(2) 0.0394(9) Uani 1 1 d . . . . .
O8 O 1.0953(4) 0.2638(3) 0.5978(2) 0.0757(12) Uani 1 1 d . . . . .
H8A H 1.113350 0.203708 0.613825 0.114 Uiso 1 1 d G . . . .
H8B H 1.021415 0.262689 0.569292 0.114 Uiso 1 1 d G . . . .
C9 C 0.5591(4) 0.1041(3) 0.3797(2) 0.0286(9) Uani 1 1 d . . . . .
C2 C 1.1958(4) 0.4789(3) 0.7233(2) 0.0306(10) Uani 1 1 d . . . . .
C3 C 1.0567(4) 0.6288(3) 0.7189(2) 0.0309(10) Uani 1 1 d . . . . .
C5 C 0.8029(4) 0.5897(3) 0.5799(2) 0.0299(9) Uani 1 1 d . . . . .
C4 C 0.9158(4) 0.5826(3) 0.6352(2) 0.0294(9) Uani 1 1 d . . . . .
C10 C 0.3895(4) 0.0585(3) 0.3139(2) 0.0286(10) Uani 1 1 d . . . . .
C12 C 0.2225(4) 0.1631(3) 0.2279(2) 0.0310(10) Uani 1 1 d . . . . .
C11 C 0.3249(4) 0.2212(3) 0.2646(2) 0.0294(9) Uani 1 1 d . . . . .
C8 C 0.6772(4) 0.0952(3) 0.4315(2) 0.0309(10) Uani 1 1 d . . . . .
C1 C 1.2699(4) 0.5355(3) 0.7774(2) 0.0323(10) Uani 1 1 d . . . . .
C6 C 0.7282(4) 0.5238(3) 0.5354(2) 0.0325(10) Uani 1 1 d . . . . .
C7 C 0.7891(4) 0.1541(3) 0.4525(2) 0.0309(10) Uani 1 1 d . . . . .
H9 H 0.620(4) 0.719(3) 0.487(2) 0.036(12) Uiso 1 1 d . . . . .
H14 H 0.835(5) -0.020(4) 0.545(2) 0.060(16) Uiso 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
H3A O3 H3B 109.5 . . ?
H9A O9 H9B 109.5 . . ?
H10A O10 H10B 109.5 . . ?
N16 N18 C10 111.0(3) . . ?
N16 N18 C11 125.0(3) . . ?
C11 N18 C10 124.0(3) . . ?
N5 N4 C2 125.1(3) . . ?
N5 N4 C3 110.9(3) . . ?
C2 N4 C3 124.0(3) . . ?
C9 N16 N18 100.3(3) . . ?
N19 N20 C12 122.3(3) . . ?
C4 N5 N4 100.6(3) . . ?
C10 N17 C9 102.3(3) . . ?
N8 N9 H9 119(3) . . ?
N10 N9 N8 115.9(4) . . ?
N10 N9 H9 125(3) . . ?
N9 N8 C5 104.7(3) . . ?
O12 N21 O11 123.1(3) . . ?
O12 N21 C12 120.3(3) . . ?
O11 N21 C12 116.6(3) . . ?
H22A N22 H22B 120.0 . . ?
C11 N22 H22A 120.0 . . ?
C11 N22 H22B 120.0 . . ?
C3 N7 C4 103.0(3) . . ?
O2 N1 C1 117.8(3) . . ?
O1 N1 O2 122.3(3) . . ?
O1 N1 C1 119.8(4) . . ?
N14 N15 C8 104.9(3) . . ?
O6 N12 C7 117.8(3) . . ?
O7 N12 O6 125.2(4) . . ?
O7 N12 C7 117.0(3) . . ?
H6A N6 H6B 120.0 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
N9 N10 C6 102.0(3) . . ?
N2 N3 C3 116.3(3) . . ?
N3 N2 C1 122.2(3) . . ?
N20 N19 C10 115.9(3) . . ?
O4 N11 O5 125.2(4) . . ?
O4 N11 C6 117.0(3) . . ?
O5 N11 C6 117.7(3) . . ?
N14 N13 C7 102.1(4) . . ?
N15 N14 N13 116.2(4) . . ?
N15 N14 H14 122(3) . . ?
N13 N14 H14 121(3) . . ?
H8A O8 H8B 109.5 . . ?
N16 C9 N17 116.8(4) . . ?
N16 C9 C8 123.1(4) . . ?
N17 C9 C8 120.1(4) . . ?
N4 C2 C1 109.3(4) . . ?
N6 C2 N4 119.1(4) . . ?
N6 C2 C1 131.6(4) . . ?
N7 C3 N4 108.8(3) . . ?
N7 C3 N3 129.1(4) . . ?
N3 C3 N4 122.1(4) . . ?
N8 C5 C4 117.8(4) . . ?
N8 C5 C6 105.8(3) . . ?
C6 C5 C4 136.4(4) . . ?
N5 C4 N7 116.6(4) . . ?
N5 C4 C5 122.3(4) . . ?
N7 C4 C5 121.0(4) . . ?
N17 C10 N18 109.6(3) . . ?
N17 C10 N19 128.1(4) . . ?
N19 C10 N18 122.3(4) . . ?
N20 C12 N21 113.0(3) . . ?
N20 C12 C11 126.2(4) . . ?
C11 C12 N21 120.7(4) . . ?
N18 C11 C12 109.4(4) . . ?
N22 C11 N18 119.3(4) . . ?
N22 C11 C12 131.3(4) . . ?
N15 C8 C9 118.4(4) . . ?
N15 C8 C7 105.5(3) . . ?
C7 C8 C9 136.1(4) . . ?
N2 C1 N1 114.0(4) . . ?
N2 C1 C2 126.1(4) . . ?
C2 C1 N1 119.9(4) . . ?
N10 C6 N11 118.0(4) . . ?
N10 C6 C5 111.6(4) . . ?
C5 C6 N11 130.3(4) . . ?
N13 C7 N12 119.0(4) . . ?
N13 C7 C8 111.2(4) . . ?
C8 C7 N12 129.8(4) . . ?
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
O3 H3A 0.8700 . ?
O3 H3B 0.8698 . ?
O9 H9A 0.8699 . ?
O9 H9B 0.8700 . ?
O12 N21 1.222(4) . ?
O4 N11 1.217(4) . ?
O11 N21 1.239(4) . ?
O10 H10A 0.8695 . ?
O10 H10B 0.8700 . ?
O6 N12 1.225(4) . ?
O5 N11 1.234(4) . ?
O2 N1 1.247(4) . ?
O7 N12 1.222(4) . ?
N18 N16 1.359(4) . ?
N18 C10 1.378(5) . ?
N18 C11 1.369(5) . ?
N4 N5 1.362(4) . ?
N4 C2 1.370(5) . ?
N4 C3 1.385(5) . ?
O1 N1 1.229(4) . ?
N16 C9 1.340(5) . ?
N20 N19 1.305(4) . ?
N20 C12 1.339(5) . ?
N5 C4 1.329(5) . ?
N17 C9 1.368(5) . ?
N17 C10 1.319(5) . ?
N9 N8 1.322(5) . ?
N9 N10 1.315(5) . ?
N9 H9 0.92(4) . ?
N8 C5 1.338(5) . ?
N21 C12 1.442(5) . ?
N22 H22A 0.8800 . ?
N22 H22B 0.8800 . ?
N22 C11 1.296(5) . ?
N7 C3 1.314(5) . ?
N7 C4 1.368(5) . ?
N1 C1 1.428(5) . ?
N15 N14 1.312(5) . ?
N15 C8 1.337(5) . ?
N12 C7 1.446(5) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C2 1.297(5) . ?
N10 C6 1.322(5) . ?
N3 N2 1.307(4) . ?
N3 C3 1.350(5) . ?
N2 C1 1.336(5) . ?
N19 C10 1.359(5) . ?
N11 C6 1.451(5) . ?
N13 N14 1.315(5) . ?
N13 C7 1.321(5) . ?
N14 H14 0.90(5) . ?
O8 H8A 0.8701 . ?
O8 H8B 0.8700 . ?
C9 C8 1.461(5) . ?
C2 C1 1.416(6) . ?
C5 C4 1.462(5) . ?
C5 C6 1.383(5) . ?
C12 C11 1.413(5) . ?
C8 C7 1.394(5) . ?
