#------------------------------------------------------------------------------
#$Date: 2022-03-03 21:54:07 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273232 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519322.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_4519322
loop_
_publ_author_name
'Zhang, Guojie'
'Yi, Zhenxin'
'Cheng, Guangbin'
'Yang, Wei'
'Yang, Hongwei'
_publ_section_title
;
 Polynitro-Functionalized Azopyrazole with High Performance and Low
 Sensitivity as Novel Energetic Materials.
;
_journal_issue                   8
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              10594
_journal_page_last               10604
_journal_paper_doi               10.1021/acsami.2c00154
_journal_volume                  14
_journal_year                    2022
_chemical_formula_moiety         '0.5(C12 K4 N20 O16)'
_chemical_formula_sum            'C6 K2 N10 O8'
_chemical_formula_weight         418.36
_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_primary     dual
_audit_creation_date             2019-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.744(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9980(5)
_cell_length_b                   4.7624(3)
_cell_length_c                   15.5601(10)
_cell_measurement_reflns_used    3454
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.489
_cell_measurement_theta_min      3.204
_cell_volume                     657.16(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'bruker d8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6109
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.297
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0537 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.9100. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0292
_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)+(0.0382P)²+0.4452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1317
_reflns_number_total             1487
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am2c00154_si_002.cif
_cod_data_source_block           220191011_0m
_cod_database_code               4519322
_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   0.939
_shelx_estimated_absorpt_t_min   0.890
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
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
K1 K 0.80672(4) 0.76685(8) 0.39767(3) 0.02080(14) Uani 1 1 d . . . . .
O4 O 0.56570(13) 0.4269(3) 0.36398(8) 0.0201(3) Uani 1 1 d . . . . .
O3 O 0.39031(14) 0.4218(3) 0.25002(8) 0.0248(3) Uani 1 1 d . . . . .
O2 O -0.04118(14) 0.2584(3) 0.35485(9) 0.0234(3) Uani 1 1 d . . . . .
O1 O 0.13717(15) 0.1386(3) 0.28481(9) 0.0267(3) Uani 1 1 d . . . . .
N5 N 0.43482(15) 0.4636(3) 0.32754(9) 0.0162(3) Uani 1 1 d . . . . .
N3 N 0.12250(16) 0.6707(3) 0.43679(10) 0.0180(3) Uani 1 1 d . . . . .
N1 N 0.50044(15) 0.9144(3) 0.46887(9) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.23284(15) 0.8429(3) 0.47472(10) 0.0179(3) Uani 1 1 d . . . . .
N4 N 0.08556(16) 0.2890(3) 0.33625(10) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.17900(18) 0.5094(3) 0.37934(11) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.33065(17) 0.5717(3) 0.38017(11) 0.0143(3) Uani 1 1 d . . . . .
C3 C 0.36045(18) 0.7815(3) 0.44310(11) 0.0150(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'
K K 0.2009 0.2494 '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
K1 K1 K1 117.314(9) 1_545 3_776 ?
K1 K1 K1 62.687(9) 1_565 3_776 ?
K1 K1 K1 180.0 1_545 1_565 ?
O4 K1 K1 52.93(3) . 1_545 ?
O4 K1 K1 127.07(3) . 1_565 ?
O4 K1 K1 150.65(3) . 3_776 ?
O4 K1 O3 67.32(4) . 2_655 ?
O4 K1 O2 148.67(4) . 1_665 ?
O4 K1 O2 81.34(4) . 1_655 ?
O4 K1 O1 87.28(4) . 2_655 ?
O4 K1 N3 133.63(4) . 1_655 ?
O4 K1 N3 79.28(4) . 3_666 ?
O4 K1 N1 59.23(4) . . ?
O4 K1 N2 110.17(4) . 3_676 ?
O3 K1 K1 74.46(3) 2_655 1_565 ?
O3 K1 K1 135.67(3) 2_655 3_776 ?
O3 K1 K1 105.54(3) 2_655 1_545 ?
O3 K1 O2 81.46(4) 2_655 1_665 ?
O3 K1 O2 107.02(4) 2_655 1_655 ?
O3 K1 O1 57.17(4) 2_655 2_655 ?
O3 K1 N3 146.58(4) 2_655 3_666 ?
O3 K1 N3 134.52(4) 2_655 1_655 ?
O3 K1 N1 76.17(4) 2_655 . ?
O3 K1 N2 105.91(4) 2_655 3_676 ?
O2 K1 K1 146.21(3) 1_655 1_565 ?
O2 K1 K1 145.31(3) 1_665 1_545 ?
O2 K1 K1 34.69(3) 1_665 1_565 ?
O2 K1 K1 102.63(3) 1_655 3_776 ?
O2 K1 K1 57.06(3) 1_665 3_776 ?
O2 K1 K1 33.79(3) 1_655 1_545 ?
O2 K1 O2 111.52(4) 1_665 1_655 ?
O2 K1 O1 77.50(4) 1_665 2_655 ?
O2 K1 O1 57.23(4) 1_655 2_655 ?
O2 K1 N3 131.83(4) 1_665 3_666 ?
O2 K1 N3 67.45(4) 1_655 3_666 ?
O2 K1 N1 112.01(4) 1_665 . ?
O2 K1 N1 136.32(4) 1_655 . ?
O1 K1 K1 78.36(3) 2_655 1_545 ?
O1 K1 K1 101.64(3) 2_655 1_565 ?
O1 K1 K1 119.61(3) 2_655 3_776 ?
O1 K1 N3 124.41(4) 2_655 3_666 ?
O1 K1 N1 130.94(4) 2_655 . ?
N3 K1 K1 129.29(3) 3_666 1_565 ?
N3 K1 K1 99.28(3) 1_655 1_565 ?
N3 K1 K1 75.71(3) 3_666 3_776 ?
N3 K1 K1 49.57(3) 1_655 3_776 ?
N3 K1 K1 80.72(3) 1_655 1_545 ?
N3 K1 K1 50.71(3) 3_666 1_545 ?
N3 K1 O2 54.79(4) 1_655 1_655 ?
N3 K1 O2 71.32(4) 1_655 1_665 ?
N3 K1 O1 81.32(4) 1_655 2_655 ?
N3 K1 N3 71.10(4) 1_655 3_666 ?
N3 K1 N1 147.73(4) 1_655 . ?
N1 K1 K1 103.61(3) . 3_776 ?
N1 K1 K1 77.38(3) . 1_565 ?
N1 K1 K1 102.62(3) . 1_545 ?
N1 K1 N3 86.12(4) . 3_666 ?
N2 K1 K1 48.17(3) 3_676 1_565 ?
N2 K1 K1 52.36(3) 3_676 3_776 ?
N2 K1 K1 131.84(3) 3_676 1_545 ?
N2 K1 O2 147.03(4) 3_676 1_655 ?
N2 K1 O2 75.10(4) 3_676 1_665 ?
N2 K1 O1 149.80(4) 3_676 2_655 ?
N2 K1 N3 101.46(4) 3_676 1_655 ?
N2 K1 N3 84.01(4) 3_676 3_666 ?
N2 K1 N1 52.31(4) 3_676 . ?
N5 O4 K1 133.05(10) . . ?
N5 O3 K1 157.63(11) . 2_645 ?
K1 O2 K1 111.52(4) 1_445 1_455 ?
N4 O2 K1 116.41(10) . 1_455 ?
N4 O2 K1 130.78(10) . 1_445 ?
N4 O1 K1 129.59(11) . 2_645 ?
O4 N5 C2 116.95(14) . . ?
O3 N5 O4 124.09(14) . . ?
O3 N5 C2 118.93(14) . . ?
K1 N3 K1 108.90(4) 1_455 3_666 ?
N2 N3 K1 90.69(10) . 3_666 ?
N2 N3 K1 129.28(11) . 1_455 ?
C1 N3 K1 115.31(10) . 1_455 ?
C1 N3 K1 96.55(10) . 3_666 ?
C1 N3 N2 107.85(13) . . ?
N1 N1 K1 121.35(14) 3_676 . ?
N1 N1 C3 112.74(17) 3_676 . ?
C3 N1 K1 125.57(10) . . ?
N3 N2 K1 123.08(10) . 3_676 ?
N3 N2 C3 108.48(14) . . ?
C3 N2 K1 128.38(11) . 3_676 ?
O2 N4 C1 117.94(15) . . ?
O1 N4 O2 123.62(14) . . ?
O1 N4 C1 118.43(14) . . ?
N3 C1 N4 118.08(14) . . ?
N3 C1 C2 110.65(14) . . ?
C2 C1 N4 130.82(16) . . ?
C1 C2 N5 130.46(15) . . ?
C3 C2 N5 126.14(14) . . ?
C3 C2 C1 103.33(14) . . ?
N2 C3 N1 124.92(15) . . ?
N2 C3 C2 109.63(14) . . ?
C2 C3 N1 125.44(15) . . ?
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
K1 K1 4.7624(3) 1_545 ?
K1 K1 4.8396(8) 3_776 ?
K1 K1 4.7624(3) 1_565 ?
K1 O4 2.6860(12) . ?
K1 O3 2.7550(13) 2_655 ?
K1 O2 2.8472(13) 1_665 ?
K1 O2 2.9135(14) 1_655 ?
K1 O1 3.0292(15) 2_655 ?
K1 N3 2.8405(15) 1_655 ?
K1 N3 3.2904(16) 3_666 ?
K1 N1 3.2172(14) . ?
K1 N2 2.7862(15) 3_676 ?
O4 N5 1.2300(18) . ?
O3 N5 1.2212(19) . ?
O2 N4 1.2317(19) . ?
O1 N4 1.223(2) . ?
N5 C2 1.440(2) . ?
N3 N2 1.345(2) . ?
N3 C1 1.342(2) . ?
N1 N1 1.267(3) 3_676 ?
N1 C3 1.406(2) . ?
N2 C3 1.355(2) . ?
N4 C1 1.438(2) . ?
C1 C2 1.394(2) . ?
C2 C3 1.393(2) . ?
