#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:16:37 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/23/7242397.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_7242397
loop_
_publ_author_name
'Yang, Feng'
'Xu, Yuangang'
'Wang, Pengcheng'
'Lin, Qiuhan'
'Bi, Fuqiang'
'Liu, Ning'
'Lu, Ming'
_publ_section_title
;
 Pyrazolo[1,5-a]pyrimidine with similar
 “amino--nitro--amino” arrangement characteristics to TATB:
 a novel heat-resistant explosive with fused structure
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              2801
_journal_page_last               2808
_journal_paper_doi               10.1039/D1CE00049G
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C6 H3 Cl N6 O4, C2 H3 N'
_chemical_formula_sum            'C8 H6 Cl N7 O4'
_chemical_formula_weight         299.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-15 deposited with the CCDC.	2021-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.872(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0127(13)
_cell_length_b                   4.6953(7)
_cell_length_c                   23.988(3)
_cell_measurement_reflns_used    2713
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.32
_cell_measurement_theta_min      2.43
_cell_volume                     1237.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0691
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11982
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_min         2.430
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0762P)²+0.6350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1441
_reflns_number_total             2846
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00049g2.cif
_cod_data_source_block           YF027_a
_cod_depositor_comments
'Adding full bibliography for 7242396--7242399.cif.'
_cod_original_cell_volume        1237.6(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7242397
_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_min   0.936
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.1323(3) 0.3394(7) 0.44346(14) 0.0462(9) Uani 1 1 d . . . . .
H1 H 0.062671 0.432223 0.453741 0.055 Uiso 1 1 calc R U . . .
C2 C 0.1922(3) 0.1331(7) 0.47597(13) 0.0407(8) Uani 1 1 d . . . . .
C3 C 0.2913(3) 0.0428(7) 0.44627(13) 0.0391(8) Uani 1 1 d . . . . .
C4 C 0.4621(3) -0.1632(7) 0.41864(15) 0.0496(9) Uani 1 1 d . . . . .
C5 C 0.4563(3) -0.0032(8) 0.36885(14) 0.0500(9) Uani 1 1 d . . . . .
C6 C 0.3619(3) 0.1939(8) 0.35764(14) 0.0460(9) Uani 1 1 d . . . . .
Cl1 Cl 0.57442(8) -0.3996(2) 0.43441(4) 0.0660(4) Uani 1 1 d . . . . .
N1 N 0.2815(2) 0.2068(6) 0.39927(10) 0.0408(7) Uani 1 1 d . . . . .
N2 N 0.1836(2) 0.3914(6) 0.39657(11) 0.0498(7) Uani 1 1 d . . . . .
N3 N 0.3819(2) -0.1431(5) 0.45709(11) 0.0449(7) Uani 1 1 d . . . . .
N4 N 0.1598(3) 0.0281(7) 0.52824(12) 0.0506(7) Uani 1 1 d . . . . .
O1 O 0.0771(2) 0.1497(6) 0.55046(10) 0.0622(7) Uani 1 1 d . . . . .
O2 O 0.2142(3) -0.1771(6) 0.54898(12) 0.0835(10) Uani 1 1 d . . . . .
N5 N 0.5459(3) -0.0321(11) 0.32737(16) 0.0791(11) Uani 1 1 d . U . . .
O3A O 0.6509(8) -0.067(3) 0.3436(5) 0.106(4) Uani 0.406(12) 1 d . U P A 1
O3B O 0.5994(7) -0.279(2) 0.3253(3) 0.104(3) Uani 0.594(12) 1 d . U P A 2
O4 O 0.5404(4) 0.1067(10) 0.28778(17) 0.1344(16) Uani 1 1 d . U . . .
N6 N 0.3404(3) 0.3645(7) 0.31539(12) 0.0616(9) Uani 1 1 d . . . . .
H6A H 0.278681 0.477108 0.314505 0.074 Uiso 1 1 calc R U . . .
H6B H 0.387807 0.364668 0.288340 0.074 Uiso 1 1 calc R U . . .
N7 N 0.1643(4) 0.7992(12) 0.2702(2) 0.1230(18) Uani 1 1 d . . . . .
C7 C 0.1395(4) 0.8866(11) 0.2276(2) 0.0793(13) Uani 1 1 d . . . . .
C8 C 0.1084(4) 1.0015(15) 0.1730(2) 0.1128(19) Uani 1 1 d . . . . .
H6 H 0.126510 1.201552 0.172920 0.169 Uiso 1 1 calc R U . . .
H5 H 0.023207 0.973441 0.163519 0.169 Uiso 1 1 calc R U . . .
H4 H 0.154882 0.906472 0.146121 0.169 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
N2 C1 C2 113.3(3) . . ?
N2 C1 H1 123.3 . . ?
C2 C1 H1 123.3 . . ?
C1 C2 C3 106.4(3) . . ?
C1 C2 N4 127.2(3) . . ?
C3 C2 N4 126.4(3) . . ?
N3 C3 N1 123.0(3) . . ?
N3 C3 C2 133.8(3) . . ?
N1 C3 C2 103.2(3) . . ?
N3 C4 C5 124.0(3) . . ?
N3 C4 Cl1 113.9(3) . . ?
C5 C4 Cl1 122.1(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 N5 117.3(4) . . ?
C4 C5 N5 122.4(4) . . ?
N6 C6 N1 116.4(3) . . ?
N6 C6 C5 130.5(3) . . ?
N1 C6 C5 113.2(3) . . ?
C3 N1 C6 123.7(3) . . ?
C3 N1 N2 114.3(2) . . ?
C6 N1 N2 122.0(3) . . ?
C1 N2 N1 102.8(2) . . ?
C4 N3 C3 115.8(3) . . ?
O2 N4 O1 123.2(3) . . ?
O2 N4 C2 119.3(3) . . ?
O1 N4 C2 117.5(3) . . ?
O4 N5 O3A 109.9(6) . . ?
O4 N5 O3B 118.1(4) . . ?
O4 N5 C5 120.8(4) . . ?
O3A N5 C5 118.1(6) . . ?
O3B N5 C5 116.0(5) . . ?
C6 N6 H6A 120.0 . . ?
C6 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
N7 C7 C8 179.4(6) . . ?
C7 C8 H6 109.5 . . ?
C7 C8 H5 109.5 . . ?
H6 C8 H5 109.5 . . ?
C7 C8 H4 109.5 . . ?
H6 C8 H4 109.5 . . ?
H5 C8 H4 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
C1 N2 1.315(4) . ?
C1 C2 1.383(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.408(4) . ?
C2 N4 1.415(4) . ?
C3 N3 1.337(4) . ?
C3 N1 1.363(4) . ?
C4 N3 1.323(4) . ?
C4 C5 1.409(5) . ?
C4 Cl1 1.686(4) . ?
C5 C6 1.404(5) . ?
C5 N5 1.455(5) . ?
C6 N6 1.301(4) . ?
C6 N1 1.380(4) . ?
N1 N2 1.382(3) . ?
N4 O2 1.222(4) . ?
N4 O1 1.227(3) . ?
N5 O4 1.150(5) . ?
N5 O3A 1.207(10) . ?
N5 O3B 1.302(8) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 C7 1.117(5) . ?
C7 C8 1.436(7) . ?
C8 H6 0.9600 . ?
C8 H5 0.9600 . ?
C8 H4 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H6 O3A^a 0.96 2.73 3.379(11) 125.2 2_665 yes
N6 H6B O4 0.86 2.33 3.095(4) 147.8 2_655 yes
N6 H6B O4 0.86 2.07 2.637(5) 122.6 . yes
N6 H6A N7 0.86 2.20 2.969(6) 149.5 . yes
C1 H1 O1 0.93 2.49 3.338(4) 151.2 3_566 yes
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
N2 C1 C2 C3 -0.6(4) . . . . ?
N2 C1 C2 N4 -179.5(3) . . . . ?
C1 C2 C3 N3 177.9(3) . . . . ?
N4 C2 C3 N3 -3.2(6) . . . . ?
C1 C2 C3 N1 0.7(3) . . . . ?
N4 C2 C3 N1 179.6(3) . . . . ?
N3 C4 C5 C6 0.5(5) . . . . ?
Cl1 C4 C5 C6 -179.3(3) . . . . ?
N3 C4 C5 N5 -179.7(3) . . . . ?
Cl1 C4 C5 N5 0.6(5) . . . . ?
C4 C5 C6 N6 178.8(3) . . . . ?
N5 C5 C6 N6 -1.0(6) . . . . ?
C4 C5 C6 N1 -0.1(5) . . . . ?
N5 C5 C6 N1 -179.9(3) . . . . ?
N3 C3 N1 C6 1.5(5) . . . . ?
C2 C3 N1 C6 179.0(3) . . . . ?
N3 C3 N1 N2 -178.2(3) . . . . ?
C2 C3 N1 N2 -0.6(3) . . . . ?
N6 C6 N1 C3 -179.9(3) . . . . ?
C5 C6 N1 C3 -0.8(4) . . . . ?
N6 C6 N1 N2 -0.3(4) . . . . ?
C5 C6 N1 N2 178.8(3) . . . . ?
C2 C1 N2 N1 0.2(4) . . . . ?
C3 N1 N2 C1 0.3(3) . . . . ?
C6 N1 N2 C1 -179.4(3) . . . . ?
C5 C4 N3 C3 0.1(5) . . . . ?
Cl1 C4 N3 C3 179.8(2) . . . . ?
N1 C3 N3 C4 -1.0(4) . . . . ?
C2 C3 N3 C4 -177.7(3) . . . . ?
C1 C2 N4 O2 171.9(3) . . . . ?
C3 C2 N4 O2 -6.8(5) . . . . ?
C1 C2 N4 O1 -7.8(5) . . . . ?
C3 C2 N4 O1 173.5(3) . . . . ?
C6 C5 N5 O4 1.8(7) . . . . ?
C4 C5 N5 O4 -178.1(4) . . . . ?
C6 C5 N5 O3A 142.0(10) . . . . ?
C4 C5 N5 O3A -37.9(11) . . . . ?
C6 C5 N5 O3B -152.6(5) . . . . ?
C4 C5 N5 O3B 27.6(7) . . . . ?
