#------------------------------------------------------------------------------
#$Date: 2022-01-15 04:54:58 +0200 (Sat, 15 Jan 2022) $
#$Revision: 272059 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/59/1565985.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1565985
loop_
_publ_author_name
'Liu, Lin'
'Han, Zheng-Bo'
_publ_section_title
;
 Bis(dimethylamine-κN)bis[4-(1,2,4-triazol-1-yl)benzoato-κO]copper(II)
;
_journal_coeditor_code           WM4159
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x220046
_journal_paper_doi               10.1107/S2414314622000463
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          '[Cu (C9 H6 N3 O2)2 (C2 H7 N)2]'
_chemical_formula_moiety         'C22 H26 Cu N8 O4'
_chemical_formula_sum            'C22 H26 Cu N8 O4'
_chemical_formula_weight         530.06
_chemical_name_systematic
Bis(dimethylamine-κN)bis[4-(1,2,4-triazol-1-yl)benzoato-κO]copper(II)
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                72.595(2)
_cell_angle_beta                 89.376(2)
_cell_angle_gamma                87.805(2)
_cell_formula_units_Z            1
_cell_length_a                   6.3657(5)
_cell_length_b                   8.1428(7)
_cell_length_c                   12.1896(11)
_cell_measurement_reflns_used    1477
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.62
_cell_volume                     602.47(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.623
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  0.7845
_exptl_absorpt_correction_T_min  0.7269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             275
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.268
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0377
_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)+(0.0482P)²+0.1332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                2345
_reflns_number_total             2727
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm4159sup1.cif
_cod_data_source_block           I
_cod_database_code               1565985
_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   0.727
_shelx_estimated_absorpt_t_max   0.784
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 1.000000 0.000000 0.500000 0.03668(13) Uani d 1 . .
O O1 0.8278(3) 0.19597(19) 0.40688(13) 0.0456(4) Uani d 1 . .
N N4 0.8929(3) -0.1440(2) 0.40592(16) 0.0478(5) Uani d 1 . .
H H4 0.834029 -0.069234 0.342060 0.072 Uiso d 1 . .
O O2 1.0899(3) 0.2218(2) 0.28158(16) 0.0564(5) Uani d 1 . .
N N3 0.3345(3) 0.9752(2) -0.18059(16) 0.0470(5) Uani d 1 . .
C C8 0.1967(4) 0.9638(3) -0.0944(2) 0.0475(5) Uani d 1 . .
H H8A 0.069359 1.026329 -0.105518 0.057 Uiso calc 1 . .
N N1 0.4455(3) 0.7973(2) -0.01740(15) 0.0357(4) Uani d 1 . .
C C1 0.9149(3) 0.2671(3) 0.31047(18) 0.0397(5) Uani d 1 . .
C C2 0.7914(3) 0.4135(2) 0.22845(17) 0.0347(4) Uani d 1 . .
C C3 0.8841(3) 0.5111(3) 0.1285(2) 0.0443(5) Uani d 1 . .
H H3A 1.024977 0.489576 0.114867 0.053 Uiso calc 1 . .
C C4 0.7728(3) 0.6395(3) 0.0487(2) 0.0462(5) Uani d 1 . .
H H4A 0.838250 0.704495 -0.017864 0.055 Uiso calc 1 . .
C C5 0.5630(3) 0.6712(2) 0.06815(17) 0.0332(4) Uani d 1 . .
C C6 0.4692(3) 0.5793(3) 0.16901(19) 0.0429(5) Uani d 1 . .
H H6A 0.329651 0.603747 0.183663 0.052 Uiso calc 1 . .
C C7 0.5831(3) 0.4506(3) 0.24845(18) 0.0438(5) Uani d 1 . .
H H7A 0.518902 0.388216 0.316208 0.053 Uiso calc 1 . .
C C9 0.4888(4) 0.8692(3) -0.12927(18) 0.0437(5) Uani d 1 . .
H H9A 0.611277 0.846901 -0.165463 0.052 Uiso calc 1 . .
N N2 0.2529(3) 0.8588(2) 0.00657(16) 0.0467(5) Uani d 1 . .
C C11 1.0630(5) -0.2323(4) 0.3597(3) 0.0766(9) Uani d 1 . .
H H11A 1.164757 -0.150450 0.321505 0.115 Uiso calc 1 . .
H H11B 1.129585 -0.320275 0.421504 0.115 Uiso calc 1 . .
H H11C 1.005285 -0.283743 0.305845 0.115 Uiso calc 1 . .
C C10 0.7338(6) -0.2657(4) 0.4651(3) 0.0853(10) Uani d 1 . .
H H10A 0.624985 -0.205376 0.494376 0.128 Uiso calc 1 . .
H H10B 0.674023 -0.317305 0.411925 0.128 Uiso calc 1 . .
H H10C 0.798323 -0.353837 0.527585 0.128 Uiso calc 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 . 2_756 180.00(8) ?
O1 Cu1 N4 . . 89.16(7) ?
O1 Cu1 N4 2_756 . 90.84(7) ?
O1 Cu1 N4 . 2_756 90.84(7) ?
O1 Cu1 N4 2_756 2_756 89.16(7) ?
N4 Cu1 N4 . 2_756 180.00(7) ?
C1 O1 Cu1 . . 111.32(13) ?
C10 N4 C11 . . 111.0(2) ?
C10 N4 Cu1 . . 113.77(18) ?
C11 N4 Cu1 . . 112.97(17) ?
C10 N4 H4 . . 108.7 ?
C11 N4 H4 . . 103.5 ?
Cu1 N4 H4 . . 106.2 ?
C9 N3 C8 . . 102.46(18) ?
N2 C8 N3 . . 116.0(2) ?
N2 C8 H8A . . 122.0 ?
N3 C8 H8A . . 122.0 ?
C9 N1 N2 . . 109.03(17) ?
C9 N1 C5 . . 129.63(18) ?
N2 N1 C5 . . 121.27(17) ?
O2 C1 O1 . . 124.09(19) ?
O2 C1 C2 . . 119.7(2) ?
O1 C1 C2 . . 116.21(18) ?
C3 C2 C7 . . 118.30(18) ?
C3 C2 C1 . . 119.88(19) ?
C7 C2 C1 . . 121.79(19) ?
C4 C3 C2 . . 121.5(2) ?
C4 C3 H3A . . 119.3 ?
C2 C3 H3A . . 119.3 ?
C3 C4 C5 . . 119.5(2) ?
C3 C4 H4A . . 120.2 ?
C5 C4 H4A . . 120.2 ?
C6 C5 C4 . . 119.96(18) ?
C6 C5 N1 . . 120.69(18) ?
C4 C5 N1 . . 119.34(18) ?
C5 C6 C7 . . 119.81(19) ?
C5 C6 H6A . . 120.1 ?
C7 C6 H6A . . 120.1 ?
C6 C7 C2 . . 120.9(2) ?
C6 C7 H7A . . 119.6 ?
C2 C7 H7A . . 119.6 ?
N3 C9 N1 . . 110.8(2) ?
N3 C9 H9A . . 124.6 ?
N1 C9 H9A . . 124.6 ?
C8 N2 N1 . . 101.72(18) ?
N4 C11 H11A . . 109.5 ?
N4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N4 C10 H10A . . 109.5 ?
N4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.9611(14) ?
Cu1 O1 2_756 1.9612(14) ?
Cu1 N4 . 2.0096(19) ?
Cu1 N4 2_756 2.0096(19) ?
O1 C1 . 1.276(3) ?
N4 C10 . 1.470(4) ?
N4 C11 . 1.475(4) ?
N4 H4 . 0.9071 ?
O2 C1 . 1.240(3) ?
N3 C9 . 1.314(3) ?
N3 C8 . 1.345(3) ?
C8 N2 . 1.315(3) ?
C8 H8A . 0.9300 ?
N1 C9 . 1.343(3) ?
N1 N2 . 1.368(2) ?
N1 C5 . 1.421(2) ?
C1 C2 . 1.507(3) ?
C2 C3 . 1.380(3) ?
C2 C7 . 1.384(3) ?
C3 C4 . 1.375(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.382(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.377(3) ?
C6 C7 . 1.382(3) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
C9 H9A . 0.9300 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4 N3 1_555 1_555 2_665 0.91 2.17 3.034(3) 160 y
C9 H9A O2 1_555 1_555 2_765 0.93 2.50 3.428(3) 173 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N3 C8 N2 . . . . -0.1(3) ?
Cu1 O1 C1 O2 . . . . -2.6(3) ?
Cu1 O1 C1 C2 . . . . 176.67(13) ?
O2 C1 C2 C3 . . . . -8.7(3) ?
O1 C1 C2 C3 . . . . 172.0(2) ?
O2 C1 C2 C7 . . . . 169.3(2) ?
O1 C1 C2 C7 . . . . -10.0(3) ?
C7 C2 C3 C4 . . . . -1.6(4) ?
C1 C2 C3 C4 . . . . 176.4(2) ?
C2 C3 C4 C5 . . . . -0.5(4) ?
C3 C4 C5 C6 . . . . 2.7(3) ?
C3 C4 C5 N1 . . . . -176.5(2) ?
C9 N1 C5 C6 . . . . -162.0(2) ?
N2 N1 C5 C6 . . . . 14.7(3) ?
C9 N1 C5 C4 . . . . 17.1(3) ?
N2 N1 C5 C4 . . . . -166.2(2) ?
C4 C5 C6 C7 . . . . -2.7(3) ?
N1 C5 C6 C7 . . . . 176.47(19) ?
C5 C6 C7 C2 . . . . 0.5(4) ?
C3 C2 C7 C6 . . . . 1.6(3) ?
C1 C2 C7 C6 . . . . -176.4(2) ?
C8 N3 C9 N1 . . . . 0.0(3) ?
N2 N1 C9 N3 . . . . 0.0(3) ?
C5 N1 C9 N3 . . . . 177.02(19) ?
N3 C8 N2 N1 . . . . 0.1(3) ?
C9 N1 N2 C8 . . . . 0.0(2) ?
C5 N1 N2 C8 . . . . -177.35(18) ?

_cod_database_fobs_code 1565985
