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#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058734.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_7058734
loop_
_publ_author_name
'Yang, Xiaoming'
'Wang, Yanna'
'Li, Zhimin'
'Du, Jiang'
'Wang, Lin'
'Zhang, Tonglai'
_publ_section_title
;
 Energetic transition metal complexes based on methyl carbazate and picric
 acid: syntheses, structures, physicochemical properties and catalysis on
 the thermal decomposition of ammonium perchlorate
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14159
_journal_paper_doi               10.1039/C9NJ03591E
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C4 H16 Mn N4 O6, 2(C6 H2 N3 O7)'
_chemical_formula_sum            'C16 H20 Mn N10 O20'
_chemical_formula_weight         727.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-27 deposited with the CCDC.    2019-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.44(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.417(3)
_cell_length_b                   7.9325(16)
_cell_length_c                   24.414(5)
_cell_measurement_reflns_used    5227
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.3634
_cell_measurement_theta_min      1.7021
_cell_volume                     2736.6(10)
_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      153.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            18765
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.364
_diffrn_reflns_theta_min         3.044
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_description       block
_exptl_crystal_F_000             1484
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0541
_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)+(0.0522P)²+5.0513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3862
_reflns_number_total             4165
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj03591e2.cif
_cod_data_source_block           bwn18272
_cod_depositor_comments
'Adding full bibliography for 7058734--7058740.cif.'
_cod_original_cell_volume        2736.5(10)
_cod_database_code               7058734
_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   0.932
_shelx_estimated_absorpt_t_min   0.885
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O8(H8A,H8B)
2.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8C,H8D,H8E)
;
_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'
'-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
Mn1 Mn 0.500000 0.29217(5) 0.750000 0.02041(12) Uani 1 2 d S T P
O9 O 0.44050(10) 0.47280(19) 0.80104(6) 0.0251(3) Uani 1 1 d . . .
O5 O 0.67689(10) 0.1693(2) 0.64464(6) 0.0243(3) Uani 1 1 d . . .
O3 O 0.85493(12) 0.5231(2) 0.64767(7) 0.0374(4) Uani 1 1 d . . .
O8 O 0.54851(11) 0.0889(2) 0.70549(6) 0.0283(3) Uani 1 1 d . . .
H8A H 0.584561 0.109825 0.683222 0.034 Uiso 1 1 d R . .
H8B H 0.503990 0.025605 0.690442 0.034 Uiso 1 1 d R . .
O7 O 0.43966(11) 0.1571(2) 0.51619(7) 0.0312(3) Uani 1 1 d . . .
O1 O 0.58569(12) 0.5389(2) 0.41361(6) 0.0341(4) Uani 1 1 d . . .
O6 O 0.51694(12) 0.0217(2) 0.58734(7) 0.0347(4) Uani 1 1 d . . .
N2 N 0.82847(12) 0.3792(2) 0.63396(7) 0.0246(3) Uani 1 1 d . . .
O4 O 0.86956(12) 0.2531(3) 0.65468(9) 0.0433(5) Uani 1 1 d . . .
O2 O 0.73134(12) 0.6175(2) 0.44265(7) 0.0359(4) Uani 1 1 d . . .
O10 O 0.32439(11) 0.6600(2) 0.80309(7) 0.0330(4) Uani 1 1 d . . .
N5 N 0.51147(12) 0.1338(2) 0.55219(7) 0.0222(3) Uani 1 1 d . . .
N4 N 0.35689(12) 0.3729(2) 0.69864(7) 0.0234(3) Uani 1 1 d . . .
H4A H 0.364865 0.417846 0.665592 0.028 Uiso 1 1 calc R . .
H4B H 0.318293 0.281527 0.691092 0.028 Uiso 1 1 calc R . .
N1 N 0.66025(13) 0.5394(2) 0.44876(7) 0.0258(4) Uani 1 1 d . . .
N3 N 0.31489(12) 0.4938(2) 0.72877(7) 0.0265(4) Uani 1 1 d . . .
H3 H 0.258869 0.537405 0.715321 0.032 Uiso 1 1 calc R . .
C3 C 0.59315(13) 0.2419(2) 0.55176(8) 0.0197(3) Uani 1 1 d . . .
C2 C 0.58961(14) 0.3374(3) 0.50408(8) 0.0220(4) Uani 1 1 d . . .
H2 H 0.536001 0.330576 0.474415 0.026 Uiso 1 1 calc R . .
C6 C 0.74307(14) 0.4572(3) 0.54258(8) 0.0218(4) Uani 1 1 d . . .
H6 H 0.793519 0.531585 0.539701 0.026 Uiso 1 1 calc R . .
C5 C 0.74531(13) 0.3598(3) 0.58939(8) 0.0206(3) Uani 1 1 d . . .
C4 C 0.67174(13) 0.2457(3) 0.59926(7) 0.0197(3) Uani 1 1 d . . .
C7 C 0.36513(13) 0.5382(3) 0.77886(8) 0.0220(4) Uani 1 1 d . . .
C1 C 0.66405(14) 0.4428(3) 0.49950(8) 0.0222(4) Uani 1 1 d . . .
C8 C 0.37721(17) 0.7163(3) 0.85695(10) 0.0324(5) Uani 1 1 d . . .
H8C H 0.442094 0.744340 0.853687 0.049 Uiso 1 1 calc GR . .
H8D H 0.378484 0.626265 0.884572 0.049 Uiso 1 1 calc GR . .
H8E H 0.346659 0.816376 0.868929 0.049 Uiso 1 1 calc GR . .
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'
Mn Mn 0.3368 0.7283 '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
O9 Mn1 O9 97.95(9) . 2_656
O9 Mn1 N4 73.43(6) 2_656 2_656
O9 Mn1 N4 85.24(6) 2_656 .
O9 Mn1 N4 85.24(6) . 2_656
O9 Mn1 N4 73.43(6) . .
O8 Mn1 O9 89.99(6) 2_656 .
O8 Mn1 O9 89.99(6) . 2_656
O8 Mn1 O9 172.00(6) . .
O8 Mn1 O9 172.00(6) 2_656 2_656
O8 Mn1 O8 82.09(9) . 2_656
O8 Mn1 N4 106.47(6) . .
O8 Mn1 N4 98.02(6) 2_656 .
O8 Mn1 N4 98.02(6) . 2_656
O8 Mn1 N4 106.46(6) 2_656 2_656
N4 Mn1 N4 147.43(9) . 2_656
C7 O9 Mn1 116.03(13) . .
Mn1 O8 H8A 119.1 . .
Mn1 O8 H8B 112.0 . .
H8A O8 H8B 110.6 . .
O3 N2 C5 117.78(18) . .
O4 N2 O3 123.34(19) . .
O4 N2 C5 118.85(18) . .
C7 O10 C8 115.33(16) . .
O7 N5 C3 118.15(17) . .
O6 N5 O7 122.42(18) . .
O6 N5 C3 119.42(16) . .
Mn1 N4 H4A 109.7 . .
Mn1 N4 H4B 109.7 . .
H4A N4 H4B 108.2 . .
N3 N4 Mn1 109.73(11) . .
N3 N4 H4A 109.7 . .
N3 N4 H4B 109.7 . .
O1 N1 C1 118.19(17) . .
O2 N1 O1 123.22(18) . .
O2 N1 C1 118.59(17) . .
N4 N3 H3 121.9 . .
C7 N3 N4 116.30(16) . .
C7 N3 H3 121.9 . .
C2 C3 N5 115.69(17) . .
C2 C3 C4 123.67(18) . .
C4 C3 N5 120.64(16) . .
C3 C2 H2 120.0 . .
C3 C2 C1 120.00(18) . .
C1 C2 H2 120.0 . .
C5 C6 H6 121.2 . .
C5 C6 C1 117.53(18) . .
C1 C6 H6 121.2 . .
C6 C5 N2 116.19(17) . .
C6 C5 C4 126.25(17) . .
C4 C5 N2 117.51(17) . .
O5 C4 C3 126.62(18) . .
O5 C4 C5 122.15(17) . .
C5 C4 C3 111.16(16) . .
O9 C7 O10 122.76(18) . .
O9 C7 N3 124.23(19) . .
O10 C7 N3 113.00(17) . .
C2 C1 N1 119.40(17) . .
C2 C1 C6 121.36(18) . .
C6 C1 N1 119.24(18) . .
O10 C8 H8C 109.5 . .
O10 C8 H8D 109.5 . .
O10 C8 H8E 109.5 . .
H8C C8 H8D 109.5 . .
H8C C8 H8E 109.5 . .
H8D C8 H8E 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O9 2.1830(15) .
Mn1 O9 2.1830(15) 2_656
Mn1 O8 2.1382(16) .
Mn1 O8 2.1382(16) 2_656
Mn1 N4 2.2832(18) 2_656
Mn1 N4 2.2831(18) .
O9 C7 1.229(2) .
O5 C4 1.252(2) .
O3 N2 1.228(3) .
O8 H8A 0.8399 .
O8 H8B 0.8398 .
O7 N5 1.232(2) .
O1 N1 1.235(2) .
O6 N5 1.227(2) .
N2 O4 1.220(3) .
N2 C5 1.458(2) .
O2 N1 1.232(2) .
O10 C7 1.329(2) .
O10 C8 1.453(3) .
N5 C3 1.459(2) .
N4 H4A 0.9100 .
N4 H4B 0.9100 .
N4 N3 1.416(2) .
N1 C1 1.449(2) .
N3 H3 0.8800 .
N3 C7 1.339(3) .
C3 C2 1.381(3) .
C3 C4 1.452(3) .
C2 H2 0.9500 .
C2 C1 1.382(3) .
C6 H6 0.9500 .
C6 C5 1.374(3) .
C6 C1 1.393(3) .
C5 C4 1.450(3) .
C8 H8C 0.9800 .
C8 H8D 0.9800 .
C8 H8E 0.9800 .
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
Mn1 O9 C7 O10 -174.48(15)
Mn1 O9 C7 N3 6.5(3)
Mn1 N4 N3 C7 1.0(2)
O3 N2 C5 C6 46.5(3)
O3 N2 C5 C4 -131.2(2)
O7 N5 C3 C2 -13.2(3)
O7 N5 C3 C4 166.78(18)
O1 N1 C1 C2 8.0(3)
O1 N1 C1 C6 -172.40(19)
O6 N5 C3 C2 165.53(18)
O6 N5 C3 C4 -14.5(3)
N2 C5 C4 O5 2.0(3)
N2 C5 C4 C3 179.00(16)
O4 N2 C5 C6 -131.6(2)
O4 N2 C5 C4 50.7(3)
O2 N1 C1 C2 -171.78(19)
O2 N1 C1 C6 7.8(3)
N5 C3 C2 C1 -179.44(17)
N5 C3 C4 O5 -4.0(3)
N5 C3 C4 C5 179.20(17)
N4 N3 C7 O9 -5.2(3)
N4 N3 C7 O10 175.77(17)
C3 C2 C1 N1 178.69(18)
C3 C2 C1 C6 -0.9(3)
C2 C3 C4 O5 176.0(2)
C2 C3 C4 C5 -0.9(3)
C6 C5 C4 O5 -175.47(19)
C6 C5 C4 C3 1.5(3)
C5 C6 C1 N1 -178.13(18)
C5 C6 C1 C2 1.4(3)
C4 C3 C2 C1 0.6(3)
C1 C6 C5 N2 -179.36(17)
C1 C6 C5 C4 -1.9(3)
C8 O10 C7 O9 2.5(3)
C8 O10 C7 N3 -178.39(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168349436
