#------------------------------------------------------------------------------
#$Date: 2024-11-09 13:07:10 +0100 (Sat 09 de Nov de 2024) $
#$Revision: 295862 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/76/7247695.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_7247695
loop_
_publ_author_name
'Atceken, Nurunnisa'
'Hemingway, Jack'
'Bull, Craig L.'
'Liu, Xiaojiao'
'Michalchuk, Adam A. L.'
'Konar, Sumit'
'Morrison, Carole A.'
'Pulham, Colin R.'
_publ_section_title
;
 High-pressure structural studies and pressure-induced sensitisation of
 3,4,5-trinitro-1H-pyrazole.
;
_journal_issue                   46
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              31646
_journal_page_last               31654
_journal_paper_doi               10.1039/d3cp04526a
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C3 N5 O6'
_chemical_formula_sum            'C3 N5 O6'
_chemical_formula_weight         202.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc29gp8r
_audit_creation_date             2021-12-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-16 deposited with the CCDC.	2023-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 127.623(5)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   19.319(2)
_cell_length_b                   7.5668(13)
_cell_length_c                   14.458(3)
_cell_measurement_reflns_used    1713
_cell_measurement_temperature    287.2
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.86
_cell_volume                     1674.0(5)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      287.2
_diffrn_measured_fraction_theta_full 0.550
_diffrn_measured_fraction_theta_max 0.550
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.550
_diffrn_reflns_Laue_measured_fraction_max 0.550
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3579
_diffrn_reflns_point_group_measured_fraction_full 0.506
_diffrn_reflns_point_group_measured_fraction_max 0.505
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.662
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.405
_exptl_crystal_description       block
_exptl_crystal_F_000             1212
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         1493
_refine_ls_number_restraints     317
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0416
_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)+(0.0927P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1137
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.461
_reflns_Friedel_fraction_max     0.461
_reflns_number_gt                1292
_reflns_number_total             1493
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp04526a2.cif
_cod_data_source_block           2tnp_p10_h
_cod_depositor_comments
;
Adding full bibliography for 7247689--7247697.cif.

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C18 N30 O36'
_cod_original_formula_weight         1212.48
_cod_original_formula_moiety         '6(C3 N5 O6)'
_cod_original_formula_units_Z            2
_cod_database_code               7247695
_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.
;
_olex2_refinement_description
;
1. Restrained distances
 C00W-C00M \\sim C00W-C00I
 with sigma of 0.02
 N4-C00M \\sim N00A-C00I
 with sigma of 0.02
 C00M-N4 \\sim C00I-N00A
 with sigma of 0.02
 C00I-N00A \\sim N4-C00M
 with sigma of 0.05
 N4-C00M \\sim N9-C00V
 with sigma of 0.02
 N00A-C00I \\sim N4-C00M
 with sigma of 0.1
 C00W-C00I \\sim C00W-C00M
 with sigma of 0.1
2. Restrained planarity
 N00A, C00I, C00W, C00M, N4
 with sigma of 0.1
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_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'
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
O001 O 0.2917(6) 0.1935(16) 0.4295(8) 0.030(3) Uani 1 1 d . . . . .
N11 N 0.0161(7) 0.698(2) 0.1817(9) 0.020(4) Uani 1 1 d . . . . .
O003 O 0.6253(5) 0.6173(17) 0.5360(7) 0.027(3) Uani 1 1 d . . . . .
O004 O 0.4914(7) -0.1642(19) 0.4560(9) 0.035(4) Uani 1 1 d . . . . .
O005 O 0.8208(6) 0.9176(18) 0.8916(8) 0.035(3) Uani 1 1 d . . . . .
N14 N 0.1277(6) 0.897(2) 0.3302(9) 0.022(3) Uani 1 1 d . . . . .
O007 O 0.6519(5) 0.8045(16) 0.6678(7) 0.031(3) Uani 1 1 d . . . . .
N2 N 0.3439(8) 0.114(2) 0.4247(11) 0.023(3) Uani 1 1 d . . . . .
O009 O 0.9848(6) 1.0258(18) 0.8489(9) 0.027(3) Uani 1 1 d . . . . .
N00A N 0.7919(6) 0.6303(19) 0.6188(9) 0.027(4) Uani 1 1 d D . . . .
C9 C 0.4974(8) 0.134(2) 0.4871(11) 0.022(3) Uani 1 1 d . . . . .
O12 O 0.3298(6) 0.5215(19) 0.5770(8) 0.026(3) Uani 1 1 d . . . . .
O13 O 0.3516(5) 0.7928(17) 0.6395(8) 0.027(3) Uani 1 1 d . . . . .
O00E O 0.1515(6) 0.3625(17) 0.2771(7) 0.033(3) Uani 1 1 d . . . . .
O00F O 0.1698(5) 0.3399(18) 0.4389(7) 0.031(3) Uani 1 1 d . . . . .
N8 N 0.5004(7) -0.014(2) 0.4287(10) 0.025(4) Uani 1 1 d . . . . .
N7 N 0.6727(7) 0.714(2) 0.6205(10) 0.024(3) Uani 1 1 d . . . . .
C00I C 0.7616(7) 0.725(2) 0.6647(9) 0.018(4) Uani 1 1 d D . . . .
O00J O -0.0061(6) 0.5452(18) 0.1545(7) 0.024(3) Uani 1 1 d . . . . .
N4 N 0.8743(7) 0.667(2) 0.6646(10) 0.026(4) Uani 1 1 d D . . . .
N3 N 0.1593(8) 0.4301(18) 0.3612(11) 0.020(3) Uani 1 1 d . . . . .
C00M C 0.8929(7) 0.798(2) 0.7400(10) 0.015(3) Uani 1 1 d D . . . .
N1 N 0.6501(8) 0.245(2) 0.6043(10) 0.023(3) Uani 1 1 d . . . . .
C00O C 0.4280(8) 0.193(3) 0.4809(12) 0.025(4) Uani 1 1 d . . . . .
N6 N 0.9744(7) 0.887(2) 0.7966(9) 0.017(3) Uani 1 1 d . . . . .
C00Q C 0.2272(8) 0.722(2) 0.4595(10) 0.018(3) Uani 1 1 d . . . . .
O17 O 0.8241(6) 1.1207(19) 0.7879(8) 0.030(3) Uani 1 1 d . . . . .
O11 O 0.3303(7) -0.029(2) 0.3722(9) 0.035(4) Uani 1 1 d . . . . .
C10 C 0.1641(9) 0.614(2) 0.3724(12) 0.017(3) Uani 1 1 d . . . . .
O00U O 0.6692(5) 0.1095(17) 0.5737(7) 0.030(3) Uani 1 1 d . . . . .
C00V C 0.5605(7) 0.255(2) 0.5583(10) 0.021(4) Uani 1 1 d D . . . .
C00W C 0.8260(6) 0.834(2) 0.7465(9) 0.015(3) Uani 1 1 d D . . . .
O15 O -0.0258(6) 0.8333(18) 0.1271(8) 0.034(3) Uani 1 1 d . . . . .
O10 O 0.7032(6) 0.3574(19) 0.6728(8) 0.033(3) Uani 1 1 d . . . . .
O14 O 1.0245(5) 0.8306(16) 0.7783(7) 0.022(3) Uani 1 1 d . . . . .
N10 N 0.4508(6) 0.335(2) 0.5441(9) 0.025(3) Uani 1 1 d . . . . .
N9 N 0.5341(7) 0.3796(19) 0.5953(8) 0.025(3) Uani 1 1 d D . . . .
N15 N 0.8236(7) 0.969(2) 0.8139(10) 0.023(4) Uani 1 1 d . . . . .
O16 O 0.5100(6) 0.0205(18) 0.3531(8) 0.042(4) Uani 1 1 d . . . . .
N12 N 0.3095(6) 0.675(2) 0.5685(9) 0.019(3) Uani 1 1 d . . . . .
C12 C 0.1019(8) 0.733(2) 0.2921(10) 0.017(3) Uani 1 1 d . . . . .
N13 N 0.2073(6) 0.892(2) 0.4373(9) 0.022(3) 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'
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
O00J N11 O15 128.0(14) . . ?
O00J N11 C12 117.8(12) . . ?
O15 N11 C12 114.2(15) . . ?
C12 N14 N13 108.8(13) . . ?
O001 N2 C00O 117.2(15) . . ?
O001 N2 O11 125.9(14) . . ?
O11 N2 C00O 116.8(13) . . ?
N4 N00A C00I 113.5(11) . . ?
C00O C9 N8 127.8(14) . . ?
C00V C9 N8 129.4(10) . . ?
C00V C9 C00O 102.8(13) . . ?
O004 N8 C9 117.6(13) . . ?
O16 N8 O004 126.2(15) . . ?
O16 N8 C9 116.2(16) . . ?
O003 N7 C00I 116.3(11) . . ?
O007 N7 O003 127.3(11) . . ?
O007 N7 C00I 116.4(12) . . ?
N00A C00I N7 121.5(12) . . ?
N00A C00I C00W 108.2(10) . . ?
C00W C00I N7 130.0(12) . . ?
N00A N4 C00M 101.6(10) . . ?
O00E N3 C10 118.9(11) . . ?
O00F N3 O00E 121.6(14) . . ?
O00F N3 C10 119.3(11) . . ?
N4 C00M N6 117.9(9) . . ?
N4 C00M C00W 113.8(11) . . ?
C00W C00M N6 128.2(12) . . ?
O00U N1 C00V 114.5(13) . . ?
O10 N1 O00U 124.4(11) . . ?
O10 N1 C00V 121.0(13) . . ?
C9 C00O N2 129.1(15) . . ?
N10 C00O N2 121.7(12) . . ?
N10 C00O C9 109.0(13) . . ?
O009 N6 C00M 117.7(11) . . ?
O14 N6 O009 125.0(13) . . ?
O14 N6 C00M 116.7(12) . . ?
C10 C00Q N12 129.1(16) . . ?
N13 C00Q C10 113.2(13) . . ?
N13 C00Q N12 117.7(13) . . ?
C00Q C10 N3 131.3(13) . . ?
C00Q C10 C12 102.3(14) . . ?
C12 C10 N3 126.3(13) . . ?
C9 C00V N1 126.0(14) . . ?
N9 C00V C9 113.2(10) . . ?
N9 C00V N1 120.3(12) . . ?
C00I C00W C00M 102.8(12) . . ?
C00I C00W N15 129.3(10) . . ?
C00M C00W N15 127.5(12) . . ?
C00O N10 N9 111.9(11) . . ?
C00V N9 N10 103.0(11) . . ?
O005 N15 C00W 115.8(17) . . ?
O17 N15 O005 127.1(16) . . ?
O17 N15 C00W 117.1(12) . . ?
O12 N12 O13 127.5(14) . . ?
O12 N12 C00Q 114.8(12) . . ?
O13 N12 C00Q 117.7(17) . . ?
N14 C12 N11 120.8(13) . . ?
N14 C12 C10 110.5(12) . . ?
C10 C12 N11 128.7(15) . . ?
C00Q N13 N14 105.2(13) . . ?
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
O001 N2 1.211(16) . ?
N11 O00J 1.215(17) . ?
N11 O15 1.241(17) . ?
N11 C12 1.461(17) . ?
O003 N7 1.227(16) . ?
O004 N8 1.254(19) . ?
O005 N15 1.220(15) . ?
N14 C12 1.325(19) . ?
N14 N13 1.363(13) . ?
O007 N7 1.195(15) . ?
N2 C00O 1.430(19) . ?
N2 O11 1.26(2) . ?
O009 N6 1.236(18) . ?
N00A C00I 1.332(15) . ?
N00A N4 1.327(15) . ?
C9 N8 1.43(2) . ?
C9 C00O 1.364(17) . ?
C9 C00V 1.36(2) . ?
O12 N12 1.208(19) . ?
O13 N12 1.221(17) . ?
O00E N3 1.242(15) . ?
O00F N3 1.221(17) . ?
N8 O16 1.242(15) . ?
N7 C00I 1.423(15) . ?
C00I C00W 1.351(18) . ?
N4 C00M 1.349(18) . ?
N3 C10 1.396(17) . ?
C00M N6 1.427(17) . ?
C00M C00W 1.377(15) . ?
N1 O00U 1.256(17) . ?
N1 C00V 1.427(15) . ?
N1 O10 1.233(19) . ?
C00O N10 1.30(2) . ?
N6 O14 1.226(14) . ?
C00Q C10 1.37(2) . ?
C00Q N12 1.441(16) . ?
C00Q N13 1.33(2) . ?
O17 N15 1.209(19) . ?
C10 C12 1.38(2) . ?
C00V N9 1.329(17) . ?
C00W N15 1.43(2) . ?
N10 N9 1.342(15) . ?
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
O001 N2 C00O C9 -178.9(15) . . . . ?
O001 N2 C00O N10 7(3) . . . . ?
O003 N7 C00I N00A -2(2) . . . . ?
O003 N7 C00I C00W 171.5(15) . . . . ?
O007 N7 C00I N00A 180.0(13) . . . . ?
O007 N7 C00I C00W -7(2) . . . . ?
N2 C00O N10 N9 175.6(12) . . . . ?
N00A C00I C00W C00M 2.0(15) . . . . ?
N00A C00I C00W N15 175.1(16) . . . . ?
N00A N4 C00M N6 -172.4(12) . . . . ?
N00A N4 C00M C00W 4(2) . . . . ?
C9 C00O N10 N9 0(2) . . . . ?
C9 C00V N9 N10 -0.4(18) . . . . ?
O00E N3 C10 C00Q -120.9(14) . . . . ?
O00E N3 C10 C12 59.1(17) . . . . ?
O00F N3 C10 C00Q 53.3(18) . . . . ?
O00F N3 C10 C12 -126.7(14) . . . . ?
N8 C9 C00O N2 7(3) . . . . ?
N8 C9 C00O N10 -178.0(17) . . . . ?
N8 C9 C00V N1 -10(3) . . . . ?
N8 C9 C00V N9 178.1(15) . . . . ?
N7 C00I C00W C00M -172.1(14) . . . . ?
N7 C00I C00W N15 1(3) . . . . ?
C00I N00A N4 C00M -2.5(17) . . . . ?
C00I C00W N15 O005 73.3(19) . . . . ?
C00I C00W N15 O17 -106.4(18) . . . . ?
O00J N11 C12 N14 -175.9(8) . . . . ?
O00J N11 C12 C10 0.8(16) . . . . ?
N4 N00A C00I N7 175.1(14) . . . . ?
N4 N00A C00I C00W 0.3(16) . . . . ?
N4 C00M N6 O009 167.4(17) . . . . ?
N4 C00M N6 O14 -5(2) . . . . ?
N4 C00M C00W C00I -3.8(19) . . . . ?
N4 C00M C00W N15 -177.1(16) . . . . ?
N3 C10 C12 N11 3.5(19) . . . . ?
N3 C10 C12 N14 -179.6(9) . . . . ?
C00M C00W N15 O005 -115.2(16) . . . . ?
C00M C00W N15 O17 65(2) . . . . ?
N1 C00V N9 N10 -173.1(12) . . . . ?
C00O C9 N8 O004 -66(2) . . . . ?
C00O C9 N8 O16 112.6(17) . . . . ?
C00O C9 C00V N1 172.6(13) . . . . ?
C00O C9 C00V N9 0.5(19) . . . . ?
C00O N10 N9 C00V 0.2(19) . . . . ?
N6 C00M C00W C00I 172.1(14) . . . . ?
N6 C00M C00W N15 -1(3) . . . . ?
C00Q C10 C12 N11 -176.5(9) . . . . ?
C00Q C10 C12 N14 0.4(13) . . . . ?
O11 N2 C00O C9 -1(3) . . . . ?
O11 N2 C00O N10 -175.2(19) . . . . ?
C10 C00Q N12 O12 10.0(16) . . . . ?
C10 C00Q N12 O13 -172.0(12) . . . . ?
C10 C00Q N13 N14 -0.4(11) . . . . ?
O00U N1 C00V C9 0(2) . . . . ?
O00U N1 C00V N9 171.7(14) . . . . ?
C00V C9 N8 O004 117.0(18) . . . . ?
C00V C9 N8 O16 -64(2) . . . . ?
C00V C9 C00O N2 -175.4(16) . . . . ?
C00V C9 C00O N10 -0.3(19) . . . . ?
C00W C00M N6 O009 -8(2) . . . . ?
C00W C00M N6 O14 179.6(14) . . . . ?
O15 N11 C12 N14 3.7(13) . . . . ?
O15 N11 C12 C10 -179.6(10) . . . . ?
O10 N1 C00V C9 -176.6(16) . . . . ?
O10 N1 C00V N9 -5(2) . . . . ?
N12 C00Q C10 N3 0(2) . . . . ?
N12 C00Q C10 C12 -179.9(9) . . . . ?
N12 C00Q N13 N14 179.5(7) . . . . ?
C12 N14 N13 C00Q 0.7(10) . . . . ?
N13 N14 C12 N11 176.5(8) . . . . ?
N13 N14 C12 C10 -0.7(12) . . . . ?
N13 C00Q C10 N3 180.0(11) . . . . ?
N13 C00Q C10 C12 0.0(13) . . . . ?
N13 C00Q N12 O12 -169.9(9) . . . . ?
N13 C00Q N12 O13 8.1(14) . . . . ?
