#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:21:57 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301837 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/95/4319590.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_4319590
loop_
_publ_author_name
'P. Manikandan'
'R. Muthukumaran'
'K. R. Justin Thomas'
'B. Varghese'
'G. V. R. Chandramouli'
'P. T. Manoharan'
_publ_section_title
;
 Copper(II) Azide Complexes of Aliphatic and Aromatic Amine Based
 Tridentate Ligands: Novel Structure, Spectroscopy, and Magnetic
 Properties
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2378
_journal_page_last               2389
_journal_paper_doi               10.1021/ic0009223
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C13 H13 Cl Cu N8 O4'
_chemical_formula_weight         444.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.797(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7155(6)
_cell_length_b                   13.459(2)
_cell_length_c                   16.671(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     1700.5(4)
_computing_cell_refinement       CAD4
_computing_data_collection       CAD4
_computing_data_reduction        MolEn
_computing_molecular_graphics    ORTEP
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       τ-2τ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3224
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0.8
_diffrn_standards_interval_time  '1 h'
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  1.258
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   DIFABS
_exptl_crystal_colour            'Dark Green'
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       Prism
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.076
_refine_ls_goodness_of_fit_obs   1.049
_refine_ls_hydrogen_treatment    isotropic
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         2989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_restrained_S_obs      1.049
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_obs          0.0445
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0573P)²+2.8206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1276
_refine_ls_wR_factor_obs         0.1064
_reflns_number_observed          2261
_reflns_number_total             2989
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic0009223_3.cif
_cod_data_source_block           '[CuL'(ClO4)]n'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+2.8206P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+2.8206P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1700.6(4)
_cod_original_sg_symbol_H-M      'P 21/n  [No. 14]'
_cod_database_code               4319590
loop_
_symmetry_equiv_pos_as_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cu Cu 0.15445(7) 0.74785(4) 0.86187(3) 0.0424(2) Uani 1 d . .
Cl Cl -0.35000(14) 0.78728(9) 0.85699(6) 0.0470(3) Uani 1 d . .
N1 N 0.1620(4) 0.6017(2) 0.9042(2) 0.0333(7) Uani 1 d . .
N2 N 0.1807(5) 0.7956(3) 0.9757(2) 0.0459(8) Uani 1 d . .
N3 N 0.2581(4) 0.7409(2) 1.0400(2) 0.0414(8) Uani 1 d . .
N4 N 0.1318(4) 0.6966(3) 0.7499(2) 0.0416(8) Uani 1 d . .
N5 N 0.0591(4) 0.6078(2) 0.7266(2) 0.0375(7) Uani 1 d . .
N6 N 0.1380(7) 0.8867(3) 0.8271(3) 0.083(2) Uani 1 d . .
N7 N 0.0541(6) 0.9186(3) 0.7668(3) 0.0631(11) Uani 1 d . .
N8 N -0.0269(10) 0.9535(4) 0.7100(3) 0.116(2) Uani 1 d . .
C1 C 0.2584(5) 0.5761(3) 0.9776(2) 0.0349(8) Uani 1 d . .
C2 C 0.2582(6) 0.4807(3) 1.0080(3) 0.0417(10) Uani 1 d . .
C3 C 0.1588(6) 0.4084(3) 0.9630(3) 0.0463(10) Uani 1 d . .
C4 C 0.0613(6) 0.4334(3) 0.8877(3) 0.0408(9) Uani 1 d . .
C5 C 0.0654(5) 0.5303(3) 0.8600(2) 0.0337(8) Uani 1 d . .
C6 C 0.3654(5) 0.6562(3) 1.0271(3) 0.0415(9) Uani 1 d . .
C7 C 0.2275(6) 0.7794(4) 1.1102(3) 0.0517(11) Uani 1 d . .
C8 C 0.1255(7) 0.8615(4) 1.0906(4) 0.0654(15) Uani 1 d . .
C9 C 0.0998(7) 0.8688(4) 1.0071(4) 0.0628(14) Uani 1 d . .
C10 C -0.0453(6) 0.5582(3) 0.7786(3) 0.0406(9) Uani 1 d . .
C11 C 0.0874(6) 0.5820(4) 0.6526(3) 0.0497(11) Uani 1 d . .
C12 C 0.1838(6) 0.6565(4) 0.6269(3) 0.0577(13) Uani 1 d . .
C13 C 0.2093(6) 0.7257(4) 0.6885(3) 0.0540(12) Uani 1 d . .
O1 O -0.1906(5) 0.7335(3) 0.8767(3) 0.0861(13) Uani 1 d . .
O2 O -0.4899(6) 0.7263(4) 0.8729(3) 0.108(2) Uani 1 d . .
O3 O -0.3831(7) 0.8142(5) 0.7758(3) 0.124(2) Uani 1 d . .
O4 O -0.3344(8) 0.8727(5) 0.9063(4) 0.147(3) Uani 1 d . .
H2 H 0.3223(56) 0.4687(32) 1.0585(27) 0.044(12) Uiso 1 d . .
H3 H 0.1531(59) 0.3478(34) 0.9838(26) 0.048(12) Uiso 1 d . .
H4 H -0.0116(63) 0.3832(36) 0.8571(28) 0.055(13) Uiso 1 d . .
H6A H 0.4479(59) 0.6742(32) 0.9945(27) 0.048(12) Uiso 1 d . .
H6B H 0.4105(58) 0.6334(33) 1.0814(29) 0.051(12) Uiso 1 d . .
H7 H 0.2735(73) 0.7492(37) 1.1630(35) 0.072(17) Uiso 1 d . .
H8 H 0.0883(66) 0.9049(38) 1.1264(31) 0.064(15) Uiso 1 d . .
H9 H 0.0421(66) 0.9128(36) 0.9719(29) 0.055(14) Uiso 1 d . .
H10A H -0.1305(50) 0.5991(27) 0.7869(21) 0.023(9) Uiso 1 d . .
H10B H -0.0900(53) 0.4987(32) 0.7503(24) 0.040(11) Uiso 1 d . .
H11 H 0.0462(54) 0.5276(32) 0.6317(24) 0.036(12) Uiso 1 d . .
H12 H 0.2173(68) 0.6550(38) 0.5732(32) 0.069(15) Uiso 1 d . .
H13 H 0.2730(58) 0.7922(34) 0.6962(25) 0.047(12) Uiso 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'
Cu Cu 0.3201 1.2651 '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'
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
N6 Cu N4 93.7(2) . . yes
N6 Cu N2 87.9(2) . . yes
N4 Cu N2 178.24(14) . . yes
N6 Cu N1 176.4(2) . . yes
N4 Cu N1 88.97(13) . . yes
N2 Cu N1 89.42(14) . . yes
O3 Cl O4 109.8(4) . . ?
O3 Cl O1 110.9(3) . . ?
O4 Cl O1 107.9(3) . . ?
O3 Cl O2 109.1(3) . . ?
O4 Cl O2 110.4(4) . . ?
O1 Cl O2 108.7(3) . . ?
C5 N1 C1 117.9(3) . . ?
C5 N1 Cu 120.6(3) . . ?
C1 N1 Cu 121.5(3) . . ?
C9 N2 N3 105.4(4) . . ?
C9 N2 Cu 130.4(3) . . ?
N3 N2 Cu 122.5(3) . . ?
C7 N3 N2 111.1(4) . . ?
C7 N3 C6 129.3(4) . . ?
N2 N3 C6 119.5(3) . . ?
C13 N4 N5 105.1(4) . . ?
C13 N4 Cu 130.6(3) . . ?
N5 N4 Cu 122.9(2) . . ?
C11 N5 N4 111.5(4) . . ?
C11 N5 C10 129.4(4) . . ?
N4 N5 C10 119.0(3) . . ?
N7 N6 Cu 126.9(4) . . yes
N8 N7 N6 177.0(6) . . ?
N1 C1 C2 122.1(4) . . ?
N1 C1 C6 117.8(3) . . ?
C2 C1 C6 120.1(4) . . ?
C3 C2 C1 119.8(4) . . ?
C2 C3 C4 118.6(4) . . ?
C3 C4 C5 119.4(4) . . ?
N1 C5 C4 122.3(4) . . ?
N1 C5 C10 118.4(3) . . ?
C4 C5 C10 119.3(4) . . ?
N3 C6 C1 112.0(3) . . ?
N3 C7 C8 107.0(5) . . ?
C7 C8 C9 105.6(5) . . ?
N2 C9 C8 110.9(5) . . ?
N5 C10 C5 111.6(3) . . ?
N5 C11 C12 106.9(5) . . ?
C11 C12 C13 105.9(4) . . ?
N4 C13 C12 110.6(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
Cu N6 1.954(4) . yes
Cu N4 1.967(3) . yes
Cu N2 1.978(4) . yes
Cu N1 2.088(3) . yes
Cl O3 1.378(4) . ?
Cl O4 1.405(5) . ?
Cl O1 1.412(4) . ?
Cl O2 1.420(4) . ?
N1 C5 1.348(5) . ?
N1 C1 1.351(5) . ?
N2 C9 1.325(6) . ?
N2 N3 1.344(5) . ?
N3 C7 1.340(6) . ?
N3 C6 1.449(5) . ?
N4 C13 1.338(5) . ?
N4 N5 1.345(5) . ?
N5 C11 1.339(5) . ?
N5 C10 1.451(5) . ?
N6 N7 1.171(6) . ?
N7 N8 1.134(6) . ?
C1 C2 1.381(6) . ?
C1 C6 1.506(6) . ?
C2 C3 1.372(6) . ?
C3 C4 1.378(6) . ?
C4 C5 1.385(6) . ?
C5 C10 1.511(6) . ?
C7 C8 1.360(8) . ?
C8 C9 1.373(8) . ?
C11 C12 1.364(7) . ?
C12 C13 1.372(7) . ?
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
N6 Cu N1 C5 104.0(26) . . . . ?
N4 Cu N1 C5 -35.4(3) . . . . ?
N2 Cu N1 C5 145.3(3) . . . . ?
N6 Cu N1 C1 -73.7(26) . . . . ?
N4 Cu N1 C1 146.9(3) . . . . ?
N2 Cu N1 C1 -32.3(3) . . . . ?
N6 Cu N2 C9 40.3(5) . . . . ?
N4 Cu N2 C9 -161.4(45) . . . . ?
N1 Cu N2 C9 -137.4(5) . . . . ?
N6 Cu N2 N3 -156.7(4) . . . . ?
N4 Cu N2 N3 1.6(49) . . . . ?
N1 Cu N2 N3 25.6(3) . . . . ?
C9 N2 N3 C7 -0.4(5) . . . . ?
Cu N2 N3 C7 -167.1(3) . . . . ?
C9 N2 N3 C6 -177.3(4) . . . . ?
Cu N2 N3 C6 16.0(5) . . . . ?
N6 Cu N4 C13 44.9(5) . . . . ?
N2 Cu N4 C13 -113.4(46) . . . . ?
N1 Cu N4 C13 -137.4(4) . . . . ?
N6 Cu N4 N5 -150.3(3) . . . . ?
N2 Cu N4 N5 51.3(48) . . . . ?
N1 Cu N4 N5 27.3(3) . . . . ?
C13 N4 N5 C11 -0.8(5) . . . . ?
Cu N4 N5 C11 -168.8(3) . . . . ?
C13 N4 N5 C10 -176.4(4) . . . . ?
Cu N4 N5 C10 15.6(5) . . . . ?
N4 Cu N6 N7 34.0(6) . . . . ?
N2 Cu N6 N7 -146.6(6) . . . . ?
N1 Cu N6 N7 -105.3(25) . . . . ?
Cu N6 N7 N8 159.1(135) . . . . ?
C5 N1 C1 C2 -0.8(5) . . . . ?
Cu N1 C1 C2 176.9(3) . . . . ?
C5 N1 C1 C6 -179.6(3) . . . . ?
Cu N1 C1 C6 -1.9(4) . . . . ?
N1 C1 C2 C3 0.4(6) . . . . ?
C6 C1 C2 C3 179.3(4) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C1 N1 C5 C4 0.6(5) . . . . ?
Cu N1 C5 C4 -177.2(3) . . . . ?
C1 N1 C5 C10 179.0(3) . . . . ?
Cu N1 C5 C10 1.2(4) . . . . ?
C3 C4 C5 N1 0.0(6) . . . . ?
C3 C4 C5 C10 -178.4(4) . . . . ?
C7 N3 C6 C1 119.2(5) . . . . ?
N2 N3 C6 C1 -64.6(5) . . . . ?
N1 C1 C6 N3 54.8(5) . . . . ?
C2 C1 C6 N3 -124.0(4) . . . . ?
N2 N3 C7 C8 0.5(5) . . . . ?
C6 N3 C7 C8 177.0(4) . . . . ?
N3 C7 C8 C9 -0.4(6) . . . . ?
N3 N2 C9 C8 0.2(6) . . . . ?
Cu N2 C9 C8 165.4(4) . . . . ?
C7 C8 C9 N2 0.1(6) . . . . ?
C11 N5 C10 C5 120.9(4) . . . . ?
N4 N5 C10 C5 -64.4(5) . . . . ?
N1 C5 C10 N5 53.3(5) . . . . ?
C4 C5 C10 N5 -128.2(4) . . . . ?
N4 N5 C11 C12 0.6(5) . . . . ?
C10 N5 C11 C12 175.6(4) . . . . ?
N5 C11 C12 C13 -0.1(5) . . . . ?
N5 N4 C13 C12 0.7(5) . . . . ?
Cu N4 C13 C12 167.4(3) . . . . ?
C11 C12 C13 N4 -0.4(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168337378
