#------------------------------------------------------------------------------
#$Date: 2023-11-05 02:04:28 +0200 (Sun, 05 Nov 2023) $
#$Revision: 287263 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/43/7714373.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_7714373
loop_
_publ_author_name
'Li, Shuting'
'Li, Min'
'Han, Jinxi'
'Xia, Zhengqiang'
'Chen, Sanping'
'Xie, Gang'
'Gao, Sheng-Li'
'Lu, Jack'
'Yang, Qi'
_publ_section_title
;
 In situ growth of copper-based energetic complexes on GO and MXene to
 synergistically promote the thermal decomposition of ammonium perchlorate
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02686H
_journal_year                    2023
_chemical_formula_moiety         'C6 H8 Cu N18 O2'
_chemical_formula_sum            'C6 H8 Cu N18 O2'
_chemical_formula_weight         427.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-10-20
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r1)
;
_audit_update_record
;
2023-10-31 deposited with the CCDC.	2023-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                101.122(4)
_cell_angle_beta                 103.119(5)
_cell_angle_gamma                106.744(4)
_cell_formula_units_Z            2
_cell_length_a                   6.8830(18)
_cell_length_b                   9.131(3)
_cell_length_c                   12.186(3)
_cell_measurement_reflns_used    795
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.55
_cell_measurement_theta_min      2.58
_cell_volume                     686.3(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3418
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.424
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.653
_exptl_absorpt_correction_T_max  0.7954
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0576 before and 0.0359 after correction.
The Ratio of minimum to maximum transmission is 0.8677.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_description       block
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0459
_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)+(0.0469P)²+0.1301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1799
_reflns_number_total             2381
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt02686h2.cif
_cod_data_source_block           EC-Cu1
_cod_database_code               7714373
_shelx_shelxl_version_number     2014/7
_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   0.826
_shelx_estimated_absorpt_t_min   0.692
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Restrained distances
 H1A-O1
 0.85 with sigma of 0.02
 H1B-O1
 0.85 with sigma of 0.02
 H2B-O2
 0.85 with sigma of 0.02
 H2A-O2
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N9(H9), N13(H13), N14(H14), N8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cu1 Cu 0.78407(9) 0.24799(7) 0.33136(5) 0.0231(2) Uani 1 1 d . . . . .
N11 N 0.6586(6) -0.7812(4) 0.0283(4) 0.0279(9) Uani 1 1 d . . . . .
N2 N 0.7943(6) 0.0332(4) 0.2380(3) 0.0172(8) Uani 1 1 d . . . . .
N4 N 1.0194(6) 0.3668(4) 0.2913(3) 0.0211(9) Uani 1 1 d . . . . .
N18 N 0.5296(6) 0.1372(4) 0.3602(3) 0.0210(9) Uani 1 1 d . . . . .
C5 C 0.4414(7) -0.0161(5) 0.3416(4) 0.0175(10) Uani 1 1 d . . . . .
N9 N 0.5920(6) -0.5842(4) 0.1136(3) 0.0216(9) Uani 1 1 d . . . . .
H9 H 0.5342 -0.5287 0.1517 0.026 Uiso 1 1 calc R . . . .
N16 N 0.2699(6) 0.0909(5) 0.4327(3) 0.0262(9) Uani 1 1 d . . . . .
N15 N 0.2781(6) -0.0529(4) 0.3837(3) 0.0227(9) Uani 1 1 d . . . . .
O1 O 0.7361(6) 0.4504(4) 0.3927(3) 0.0347(9) Uani 1 1 d D . . . .
N17 N 0.4188(6) 0.2051(4) 0.4194(3) 0.0240(9) Uani 1 1 d . . . . .
O2 O 1.0002(5) 0.2421(4) 0.5105(3) 0.0272(8) Uani 1 1 d D . . . .
N5 N 1.1090(6) 0.5268(4) 0.3242(4) 0.0297(10) Uani 1 1 d . . . . .
N13 N 0.8609(6) -0.3724(4) 0.0812(3) 0.0224(9) Uani 1 1 d . . . . .
H13 H 0.9626 -0.3575 0.0500 0.027 Uiso 1 1 calc R . . . .
N7 N 1.2749(6) 0.4332(4) 0.2122(3) 0.0242(9) Uani 1 1 d . . . . .
N6 N 1.2597(7) 0.5642(5) 0.2771(4) 0.0313(10) Uani 1 1 d . . . . .
N1 N 0.9575(6) -0.1067(4) 0.1219(3) 0.0220(9) Uani 1 1 d . . . . .
N12 N 0.7978(6) -0.6471(4) 0.0191(3) 0.0221(9) Uani 1 1 d . . . . .
C4 C 1.1238(7) 0.3154(5) 0.2235(4) 0.0200(10) Uani 1 1 d . . . . .
N14 N 0.5068(6) -0.1298(4) 0.2845(3) 0.0221(9) Uani 1 1 d . . . . .
H14 H 0.4358 -0.2266 0.2795 0.026 Uiso 1 1 calc R . . . .
N8 N 1.0819(6) 0.1585(4) 0.1710(3) 0.0226(9) Uani 1 1 d . . . . .
H8 H 1.1590 0.1414 0.1269 0.027 Uiso 1 1 calc R . . . .
N10 N 0.5354(6) -0.7441(4) 0.0856(4) 0.0270(9) Uani 1 1 d . . . . .
C2 C 0.9380(7) 0.0256(5) 0.1774(4) 0.0194(10) Uani 1 1 d . . . . .
C1 C 0.8297(7) -0.2394(5) 0.1325(4) 0.0183(10) Uani 1 1 d . . . . .
N3 N 0.6808(6) -0.2525(4) 0.1870(3) 0.0219(9) Uani 1 1 d . . . . .
C3 C 0.6663(7) -0.1116(5) 0.2352(4) 0.0176(9) Uani 1 1 d . . . . .
C6 C 0.7521(7) -0.5272(5) 0.0725(4) 0.0193(10) Uani 1 1 d . . . . .
H1A H 0.827(6) 0.543(3) 0.415(4) 0.043(17) Uiso 1 1 d D . . . .
H1B H 0.648(8) 0.429(7) 0.431(5) 0.06(2) Uiso 1 1 d D . . . .
H2A H 1.071(9) 0.184(7) 0.490(6) 0.08(2) Uiso 1 1 d D . . . .
H2B H 0.934(7) 0.200(5) 0.553(4) 0.030(14) Uiso 1 1 d 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'
Cu Cu 0.3201 1.2651 '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
N2 Cu1 O2 93.08(13) . . ?
N4 Cu1 N2 91.25(14) . . ?
N4 Cu1 N18 173.77(16) . . ?
N4 Cu1 O1 89.21(15) . . ?
N4 Cu1 O2 93.23(14) . . ?
N18 Cu1 N2 90.80(15) . . ?
N18 Cu1 O1 87.70(15) . . ?
N18 Cu1 O2 92.53(14) . . ?
O1 Cu1 N2 169.40(15) . . ?
O1 Cu1 O2 97.46(14) . . ?
N10 N11 N12 110.1(3) . . ?
C2 N2 Cu1 123.3(3) . . ?
C3 N2 Cu1 123.6(3) . . ?
C3 N2 C2 113.0(3) . . ?
N5 N4 Cu1 125.6(3) . . ?
C4 N4 Cu1 128.8(3) . . ?
C4 N4 N5 105.5(3) . . ?
C5 N18 Cu1 127.9(3) . . ?
C5 N18 N17 106.0(3) . . ?
N17 N18 Cu1 125.6(3) . . ?
N18 C5 N15 112.5(4) . . ?
N18 C5 N14 125.0(4) . . ?
N15 C5 N14 122.5(4) . . ?
N10 N9 H9 125.9 . . ?
C6 N9 H9 125.9 . . ?
C6 N9 N10 108.3(3) . . ?
N17 N16 N15 110.8(3) . . ?
C5 N15 N16 103.4(4) . . ?
Cu1 O1 H1A 126(4) . . ?
Cu1 O1 H1B 107(4) . . ?
H1A O1 H1B 118(5) . . ?
N16 N17 N18 107.4(3) . . ?
Cu1 O2 H2A 104(5) . . ?
Cu1 O2 H2B 115(3) . . ?
H2A O2 H2B 107(5) . . ?
N6 N5 N4 107.8(3) . . ?
C1 N13 H13 115.7 . . ?
C1 N13 C6 128.6(4) . . ?
C6 N13 H13 115.7 . . ?
C4 N7 N6 103.7(3) . . ?
N5 N6 N7 111.0(4) . . ?
C2 N1 C1 114.6(4) . . ?
C6 N12 N11 106.0(4) . . ?
N4 C4 N7 112.0(4) . . ?
N4 C4 N8 124.4(4) . . ?
N7 C4 N8 123.6(4) . . ?
C5 N14 H14 115.3 . . ?
C3 N14 C5 129.4(4) . . ?
C3 N14 H14 115.3 . . ?
C4 N8 H8 114.9 . . ?
C2 N8 C4 130.2(4) . . ?
C2 N8 H8 114.9 . . ?
N11 N10 N9 106.9(3) . . ?
N1 C2 N2 125.5(4) . . ?
N1 C2 N8 112.5(4) . . ?
N8 C2 N2 121.9(4) . . ?
N1 C1 N13 113.7(4) . . ?
N1 C1 N3 127.1(4) . . ?
N3 C1 N13 119.2(4) . . ?
C1 N3 C3 113.5(4) . . ?
N2 C3 N14 122.1(4) . . ?
N3 C3 N2 126.0(4) . . ?
N3 C3 N14 111.9(4) . . ?
N9 C6 N13 128.6(4) . . ?
N12 C6 N9 108.7(4) . . ?
N12 C6 N13 122.6(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
Cu1 N2 2.098(3) . ?
Cu1 N4 1.894(3) . ?
Cu1 N18 1.901(3) . ?
Cu1 O1 2.004(4) . ?
Cu1 O2 2.367(4) . ?
N11 N12 1.362(5) . ?
N11 N10 1.289(5) . ?
N2 C2 1.371(5) . ?
N2 C3 1.350(5) . ?
N4 N5 1.349(5) . ?
N4 C4 1.317(5) . ?
N18 C5 1.306(5) . ?
N18 N17 1.355(5) . ?
C5 N15 1.323(5) . ?
C5 N14 1.377(5) . ?
N9 H9 0.8600 . ?
N9 N10 1.349(5) . ?
N9 C6 1.326(5) . ?
N16 N15 1.356(5) . ?
N16 N17 1.300(5) . ?
O1 H1A 0.85(2) . ?
O1 H1B 0.84(2) . ?
O2 H2A 0.85(2) . ?
O2 H2B 0.84(2) . ?
N5 N6 1.291(5) . ?
N13 H13 0.8600 . ?
N13 C1 1.353(5) . ?
N13 C6 1.366(5) . ?
N7 N6 1.346(5) . ?
N7 C4 1.318(5) . ?
N1 C2 1.325(5) . ?
N1 C1 1.326(5) . ?
N12 C6 1.318(5) . ?
C4 N8 1.367(5) . ?
N14 H14 0.8600 . ?
N14 C3 1.351(5) . ?
N8 H8 0.8600 . ?
N8 C2 1.356(6) . ?
C1 N3 1.332(5) . ?
N3 C3 1.349(5) . ?
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
Cu1 N2 C2 N1 176.6(3) . . . . ?
Cu1 N2 C2 N8 -1.8(6) . . . . ?
Cu1 N2 C3 N14 6.0(6) . . . . ?
Cu1 N2 C3 N3 -172.6(3) . . . . ?
Cu1 N4 N5 N6 -177.8(3) . . . . ?
Cu1 N4 C4 N7 177.7(3) . . . . ?
Cu1 N4 C4 N8 -2.4(7) . . . . ?
Cu1 N18 C5 N15 172.8(3) . . . . ?
Cu1 N18 C5 N14 -7.5(7) . . . . ?
Cu1 N18 N17 N16 -172.7(3) . . . . ?
N11 N12 C6 N9 0.3(5) . . . . ?
N11 N12 C6 N13 179.7(4) . . . . ?
N2 Cu1 N4 N5 -179.9(4) . . . . ?
N2 Cu1 N4 C4 3.3(4) . . . . ?
N4 N5 N6 N7 0.2(5) . . . . ?
N4 C4 N8 C2 -2.2(8) . . . . ?
N18 C5 N15 N16 -0.7(5) . . . . ?
N18 C5 N14 C3 -1.1(7) . . . . ?
C5 N18 N17 N16 -0.5(5) . . . . ?
C5 N14 C3 N2 1.3(7) . . . . ?
C5 N14 C3 N3 -179.9(4) . . . . ?
N15 C5 N14 C3 178.6(4) . . . . ?
N15 N16 N17 N18 0.1(5) . . . . ?
O1 Cu1 N4 N5 10.7(4) . . . . ?
O1 Cu1 N4 C4 -166.1(4) . . . . ?
N17 N18 C5 N15 0.8(5) . . . . ?
N17 N18 C5 N14 -179.5(4) . . . . ?
N17 N16 N15 C5 0.4(5) . . . . ?
O2 Cu1 N4 N5 -86.7(4) . . . . ?
O2 Cu1 N4 C4 96.5(4) . . . . ?
N5 N4 C4 N7 0.4(5) . . . . ?
N5 N4 C4 N8 -179.7(4) . . . . ?
N13 C1 N3 C3 179.6(4) . . . . ?
N7 C4 N8 C2 177.7(4) . . . . ?
N6 N7 C4 N4 -0.2(5) . . . . ?
N6 N7 C4 N8 179.9(4) . . . . ?
N1 C1 N3 C3 -0.2(7) . . . . ?
N12 N11 N10 N9 0.6(5) . . . . ?
C4 N4 N5 N6 -0.4(5) . . . . ?
C4 N7 N6 N5 0.0(5) . . . . ?
C4 N8 C2 N2 4.2(7) . . . . ?
C4 N8 C2 N1 -174.3(4) . . . . ?
N14 C5 N15 N16 179.5(4) . . . . ?
N10 N11 N12 C6 -0.6(5) . . . . ?
N10 N9 C6 N13 -179.4(4) . . . . ?
N10 N9 C6 N12 0.0(5) . . . . ?
C2 N2 C3 N14 -176.5(4) . . . . ?
C2 N2 C3 N3 4.9(6) . . . . ?
C2 N1 C1 N13 -176.2(4) . . . . ?
C2 N1 C1 N3 3.5(7) . . . . ?
C1 N13 C6 N9 -1.1(8) . . . . ?
C1 N13 C6 N12 179.5(4) . . . . ?
C1 N1 C2 N2 -2.8(7) . . . . ?
C1 N1 C2 N8 175.6(4) . . . . ?
C1 N3 C3 N2 -4.4(6) . . . . ?
C1 N3 C3 N14 176.8(4) . . . . ?
C3 N2 C2 N1 -1.0(6) . . . . ?
C3 N2 C2 N8 -179.3(4) . . . . ?
C6 N9 N10 N11 -0.4(5) . . . . ?
C6 N13 C1 N1 -177.4(4) . . . . ?
C6 N13 C1 N3 2.8(7) . . . . ?
