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#$Date: 2024-07-05 21:09:03 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293292 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/87/7248738.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_7248738
loop_
_publ_author_name
'Christopher, Imogen L.'
'Liu, Xiaojiao'
'Lloyd, Hayleigh J.'
'Bull, Craig L.'
'Funnell, Nicholas P.'
'Portius, Peter'
'Michalchuk, Adam A. L.'
'Kennedy, Stuart R.'
'Pulham, Colin R.'
'Morrison, Carole A.'
_publ_section_title
;
 Tuning energetic properties through co-crystallisation - a high-pressure
 experimental and computational study of nitrotriazolone: 4,4'-bipyridine.
;
_journal_issue                   23
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              16859
_journal_page_last               16870
_journal_paper_doi               10.1039/d4cp01595a
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C2 H2 N4 O3, C10 H8 N2'
_chemical_formula_sum            'C12 H10 N6 O3'
_chemical_formula_weight         286.26
_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_block_doi                 10.5517/ccdc.csd.cc2bvm72
_audit_creation_date             2022-05-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.766(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1472(12)
_cell_length_b                   5.6110(4)
_cell_length_c                   25.939(2)
_cell_measurement_reflns_used    2739
_cell_measurement_temperature    298.4
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      3.72
_cell_volume                     1036.6(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.4
_diffrn_measured_fraction_theta_full 0.363
_diffrn_measured_fraction_theta_max 0.333
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.363
_diffrn_reflns_Laue_measured_fraction_max 0.333
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5518
_diffrn_reflns_point_group_measured_fraction_full 0.363
_diffrn_reflns_point_group_measured_fraction_max 0.333
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.152
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0687 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.8913.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         704
_refine_ls_number_restraints     150
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0422
_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)+(0.0559P)²+1.5315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                615
_reflns_number_total             704
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cp01595a2.cif
_cod_data_source_block           3car_p08
_cod_depositor_comments
'Adding full bibliography for 7248734--7248746.cif.'
_cod_database_code               7248738
_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. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. 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
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C6(H6), C11(H11), C9(H9), C3(H3), C12(H12), C8(H8)
;
_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
O1 O 0.1850(11) -0.1542(4) 0.31137(14) 0.031(4) Uani 1 1 d . . . . .
O2 O 0.1752(11) -0.0374(4) 0.39132(13) 0.037(5) Uani 1 1 d . . . . .
O3 O 0.5236(11) 0.7177(4) 0.36895(14) 0.036(4) Uani 1 1 d . . . . .
N2 N 0.3681(13) 0.3557(5) 0.37300(16) 0.026(4) Uani 1 1 d . . . . .
N4 N 0.3861(13) 0.2378(5) 0.29174(15) 0.021(5) Uani 1 1 d . . . . .
N5 N 0.2687(13) 0.4329(6) 0.46591(17) 0.024(6) Uani 1 1 d . . . . .
N3 N 0.4701(13) 0.4536(5) 0.30002(17) 0.036(5) Uani 1 1 d . . . . .
N1 N 0.2220(13) -0.0165(5) 0.34654(15) 0.020(4) Uani 1 1 d . . . . .
N6 N 0.1223(12) 0.8120(5) 0.71895(15) 0.027(5) Uani 1 1 d . . . . .
C1 C 0.3293(15) 0.1906(6) 0.33710(19) 0.023(5) Uani 1 1 d . . . . .
C10 C 0.1685(15) 0.6655(6) 0.61768(19) 0.020(5) Uani 1 1 d . . . . .
C4 C 0.1438(16) 0.3596(6) 0.54653(19) 0.017(6) Uani 1 1 d . . . . .
H4 H 0.080607 0.257281 0.567322 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4647(15) 0.5331(6) 0.34972(19) 0.018(5) Uani 1 1 d . . . . .
C7 C 0.3234(17) 0.6453(7) 0.4826(2) 0.025(7) Uani 1 1 d . . . . .
H7 H 0.382222 0.745209 0.460351 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2022(16) 0.5832(6) 0.56469(19) 0.021(6) Uani 1 1 d . . . . .
C6 C 0.2972(16) 0.7264(7) 0.53185(19) 0.032(6) Uani 1 1 d . . . . .
H6 H 0.342606 0.874879 0.542821 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2307(16) 0.8841(6) 0.6354(2) 0.015(6) Uani 1 1 d . . . . .
H11 H 0.286776 0.988312 0.613479 0.018 Uiso 1 1 calc R U . . .
C9 C 0.0721(16) 0.5220(6) 0.65058(19) 0.024(6) Uani 1 1 d . . . . .
H9 H 0.021184 0.376793 0.639292 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1807(16) 0.2920(6) 0.4975(2) 0.025(6) Uani 1 1 d . . . . .
H3 H 0.142706 0.141512 0.485889 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2099(16) 0.9498(6) 0.68639(19) 0.029(6) Uani 1 1 d . . . . .
H12 H 0.258783 1.095262 0.698277 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0544(16) 0.6017(6) 0.7005(2) 0.020(6) Uani 1 1 d . . . . .
H8 H -0.007981 0.504564 0.722490 0.024 Uiso 1 1 calc R U . . .
H3A H 0.51(2) 0.532(9) 0.276(3) 0.06(2) Uiso 1 1 d . . . . .
H2 H 0.311(18) 0.365(9) 0.406(3) 0.061(19) 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
C1 N2 C2 106.3(3) . . ?
C1 N2 H2 125(5) . . ?
C2 N2 H2 127(4) . . ?
C1 N4 N3 101.8(4) . . ?
C7 N5 C3 118.4(4) . . ?
N4 N3 C2 113.1(4) . . ?
N4 N3 H3A 122(5) . . ?
C2 N3 H3A 125(5) . . ?
O1 N1 O2 126.0(5) . . ?
O1 N1 C1 118.6(3) . . ?
O2 N1 C1 115.4(4) . . ?
C12 N6 C8 117.0(3) . . ?
N2 C1 N1 122.2(3) . . ?
N4 C1 N2 115.4(5) . . ?
N4 C1 N1 122.2(5) . . ?
C11 C10 C5 121.0(4) . . ?
C11 C10 C9 118.2(4) . . ?
C9 C10 C5 120.8(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(5) . . ?
O3 C2 N2 127.4(3) . . ?
O3 C2 N3 129.2(4) . . ?
N3 C2 N2 103.4(5) . . ?
N5 C7 H7 118.6 . . ?
N5 C7 C6 122.9(5) . . ?
C6 C7 H7 118.6 . . ?
C4 C5 C10 121.7(4) . . ?
C6 C5 C10 120.8(5) . . ?
C6 C5 C4 117.5(3) . . ?
C7 C6 C5 119.1(5) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 C10 118.3(5) . . ?
C8 C9 H9 120.9 . . ?
N5 C3 C4 122.9(5) . . ?
N5 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
N6 C12 C11 122.6(5) . . ?
N6 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N6 C8 C9 123.8(4) . . ?
N6 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
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 1.208(6) . ?
O2 N1 1.241(4) . ?
O3 C2 1.210(7) . ?
N2 C1 1.326(7) . ?
N2 C2 1.379(7) . ?
N2 H2 0.99(6) . ?
N4 N3 1.361(7) . ?
N4 C1 1.304(5) . ?
N5 C7 1.316(8) . ?
N5 C3 1.334(7) . ?
N3 C2 1.368(6) . ?
N3 H3A 0.84(6) . ?
N1 C1 1.424(8) . ?
N6 C12 1.339(6) . ?
N6 C8 1.349(8) . ?
C10 C5 1.488(5) . ?
C10 C11 1.371(8) . ?
C10 C9 1.396(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(8) . ?
C4 C3 1.372(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.383(5) . ?
C5 C6 1.389(7) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.392(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.385(6) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C8 H8 0.9300 . ?
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
O1 N1 C1 N2 176.8(9) . . . . ?
O1 N1 C1 N4 1.0(14) . . . . ?
O2 N1 C1 N2 -3.3(14) . . . . ?
O2 N1 C1 N4 -179.1(9) . . . . ?
N4 N3 C2 O3 -178.7(10) . . . . ?
N4 N3 C2 N2 -1.1(11) . . . . ?
N5 C7 C6 C5 -2.8(17) . . . . ?
N3 N4 C1 N2 0.4(11) . . . . ?
N3 N4 C1 N1 176.4(9) . . . . ?
C1 N2 C2 O3 178.9(10) . . . . ?
C1 N2 C2 N3 1.2(10) . . . . ?
C1 N4 N3 C2 0.5(11) . . . . ?
C10 C5 C6 C7 -179.1(10) . . . . ?
C10 C11 C12 N6 -3.3(16) . . . . ?
C10 C9 C8 N6 1.1(16) . . . . ?
C4 C5 C6 C7 2.3(15) . . . . ?
C2 N2 C1 N4 -1.1(12) . . . . ?
C2 N2 C1 N1 -177.1(9) . . . . ?
C7 N5 C3 C4 0.4(16) . . . . ?
C5 C10 C11 C12 -175.3(10) . . . . ?
C5 C10 C9 C8 176.3(10) . . . . ?
C5 C4 C3 N5 -0.8(17) . . . . ?
C11 C10 C5 C4 178.5(9) . . . . ?
C11 C10 C5 C6 -0.1(15) . . . . ?
C11 C10 C9 C8 -3.9(15) . . . . ?
C9 C10 C5 C4 -1.7(16) . . . . ?
C9 C10 C5 C6 179.7(9) . . . . ?
C9 C10 C11 C12 4.9(14) . . . . ?
C3 N5 C7 C6 1.5(16) . . . . ?
C3 C4 C5 C10 -179.2(10) . . . . ?
C3 C4 C5 C6 -0.5(15) . . . . ?
C12 N6 C8 C9 0.6(15) . . . . ?
C8 N6 C12 C11 0.4(15) . . . . ?
