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#$Date: 2019-12-25 23:14:21 +0200 (Wed, 25 Dec 2019) $
#$Revision: 246004 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/15/2311589.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_2311589
loop_
_publ_author_name
'Alieva, Guloy K.'
'Ashurov, Jamshid M.'
'Kadirova, Shahnoza A.'
'Ibragimov, Bakhtiyar T.'
'Zakhidov, Kasim A.'
_publ_section_title
;
 Crystal structure of
 trans-bis-[2-(1H-benzotriazol-1-yl)acetato-κO]bis-(ethano-lamine-κ²N,O)copper(II).
;
_journal_coeditor_code           WM5481
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              233
_journal_page_last               236
_journal_paper_doi               10.1107/S2056989019000744
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          '[Cu (C8 H6 N3 O2)2 (C2 H7 N O)2]'
_chemical_formula_moiety         'C20 H26 Cu N8 O6'
_chemical_formula_sum            'C20 H26 Cu N8 O6'
_chemical_formula_weight         538.03
_chemical_name_systematic
trans-Bis[2-(1H-benzotriazol-1-yl)acetato-κO]bis(ethanolamine-κ²N,O)copper(II)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.823(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4283(4)
_cell_length_b                   4.84866(9)
_cell_length_c                   20.6944(5)
_cell_measurement_reflns_used    3723
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6500
_cell_measurement_theta_min      3.7240
_cell_volume                     1199.80(6)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2006
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.2576
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku Xcalibur Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8833
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.847
_diffrn_reflns_theta_min         3.757
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             558
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.307
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0329
_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)+(0.0480P)²+0.3640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                2152
_reflns_number_total             2444
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5481sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1199.80(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2311589
_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.
;
loop_
_space_group_symop_operation_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_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
Cu Cu 0.5000 0.5000 0.5000 0.03515(14) Uani d 1
O O2 0.53163(12) 0.2852(3) 0.58733(6) 0.0434(3) Uani d 1
O O3 0.66203(12) 0.2720(3) 0.47288(7) 0.0449(3) Uani d 1
O O1 0.46322(14) 0.5886(3) 0.64711(7) 0.0535(4) Uani d 1
N N1 0.56782(14) 0.3490(4) 0.76528(8) 0.0420(4) Uani d 1
N N4 0.62260(16) 0.7586(3) 0.54159(8) 0.0432(4) Uani d 1
N N3 0.60695(19) 0.6560(5) 0.84410(10) 0.0659(6) Uani d 1
C C7 0.57879(18) 0.2195(5) 0.70430(9) 0.0458(5) Uani d 1
H H7A 0.5484 0.0342 0.7013 0.055 Uiso calc 1
H H7B 0.6574 0.2054 0.7061 0.055 Uiso calc 1
N N2 0.64071(17) 0.5465(5) 0.79544(10) 0.0582(5) Uani d 1
C C8 0.51797(16) 0.3819(4) 0.64159(9) 0.0383(4) Uani d 1
C C3 0.50966(19) 0.5287(5) 0.84514(11) 0.0494(5) Uani d 1
C C2 0.48288(17) 0.3334(4) 0.79457(10) 0.0430(4) Uani d 1
C C10 0.74518(19) 0.4794(5) 0.49439(13) 0.0568(6) Uani d 1
H H10A 0.7391 0.6123 0.4585 0.068 Uiso calc 1
H H10B 0.8187 0.3956 0.5041 0.068 Uiso calc 1
C C9 0.73262(19) 0.6246(5) 0.55560(12) 0.0557(5) Uani d 1
H H9A 0.7405 0.4930 0.5919 0.067 Uiso calc 1
H H9B 0.7910 0.7621 0.5696 0.067 Uiso calc 1
C C1 0.3878(2) 0.1733(5) 0.78222(14) 0.0628(6) Uani d 1
H H1 0.3704 0.0434 0.7479 0.075 Uiso calc 1
C C4 0.4385(3) 0.5704(7) 0.88710(14) 0.0763(8) Uani d 1
H H4 0.4549 0.7005 0.9214 0.092 Uiso calc 1
C C6 0.3200(3) 0.2185(7) 0.82423(19) 0.0817(9) Uani d 1
H H6 0.2551 0.1146 0.8180 0.098 Uiso calc 1
C C5 0.3452(3) 0.4120(7) 0.87504(19) 0.0849(10) Uani d 1
H H5 0.2967 0.4345 0.9018 0.102 Uiso calc 1
H H4A 0.609(2) 0.836(6) 0.5773(10) 0.078(9) Uiso d 1
H H4B 0.623(2) 0.895(4) 0.5130(11) 0.063(7) Uiso d 1
H H3 0.6329(19) 0.295(5) 0.4336(6) 0.055(7) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
N4 Cu N4 3_666 . 180.0
N4 Cu O2 3_666 . 90.08(6)
N4 Cu O2 . . 89.92(6)
N4 Cu O2 3_666 3_666 89.92(6)
N4 Cu O2 . 3_666 90.08(6)
O2 Cu O2 . 3_666 180.0
C8 O2 Cu . . 123.91(12)
C10 O3 H3 . . 107.8(19)
N2 N1 C2 . . 109.84(17)
N2 N1 C7 . . 120.00(17)
C2 N1 C7 . . 129.44(18)
C9 N4 Cu . . 111.72(13)
C9 N4 H4A . . 113.6(19)
Cu N4 H4A . . 110(2)
C9 N4 H4B . . 106.4(17)
Cu N4 H4B . . 109.1(18)
H4A N4 H4B . . 106(3)
N2 N3 C3 . . 107.5(2)
N1 C7 C8 . . 111.94(16)
N1 C7 H7A . . 109.2
C8 C7 H7A . . 109.2
N1 C7 H7B . . 109.2
C8 C7 H7B . . 109.2
H7A C7 H7B . . 107.9
N3 N2 N1 . . 109.23(18)
O1 C8 O2 . . 126.26(17)
O1 C8 C7 . . 119.79(16)
O2 C8 C7 . . 113.94(17)
N3 C3 C2 . . 109.3(2)
N3 C3 C4 . . 130.7(3)
C2 C3 C4 . . 120.1(2)
N1 C2 C3 . . 104.13(18)
N1 C2 C1 . . 132.9(2)
C3 C2 C1 . . 122.9(2)
O3 C10 C9 . . 111.30(18)
O3 C10 H10A . . 109.4
C9 C10 H10A . . 109.4
O3 C10 H10B . . 109.4
C9 C10 H10B . . 109.4
H10A C10 H10B . . 108.0
N4 C9 C10 . . 110.35(18)
N4 C9 H9A . . 109.6
C10 C9 H9A . . 109.6
N4 C9 H9B . . 109.6
C10 C9 H9B . . 109.6
H9A C9 H9B . . 108.1
C2 C1 C6 . . 115.6(3)
C2 C1 H1 . . 122.2
C6 C1 H1 . . 122.2
C5 C4 C3 . . 116.9(3)
C5 C4 H4 . . 121.5
C3 C4 H4 . . 121.5
C5 C6 C1 . . 122.4(3)
C5 C6 H6 . . 118.8
C1 C6 H6 . . 118.8
C4 C5 C6 . . 122.0(3)
C4 C5 H5 . . 119.0
C6 C5 H5 . . 119.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu N4 3_666 1.9798(18)
Cu N4 . 1.9798(18)
Cu O2 . 2.0292(12)
Cu O2 3_666 2.0293(12)
Cu O3 3_666 2.4917(15)
O2 C8 . 1.270(2)
O3 C10 . 1.424(3)
O3 H3 . 0.802(10)
O1 C8 . 1.234(2)
N1 N2 . 1.349(3)
N1 C2 . 1.355(3)
N1 C7 . 1.449(2)
N4 C9 . 1.470(3)
N4 H4A . 0.885(10)
N4 H4B . 0.887(10)
N3 N2 . 1.305(3)
N3 C3 . 1.363(3)
C7 C8 . 1.530(3)
C7 H7A . 0.9700
C7 H7B . 0.9700
C3 C2 . 1.383(3)
C3 C4 . 1.413(4)
C2 C1 . 1.378(3)
C10 C9 . 1.494(3)
C10 H10A . 0.9700
C10 H10B . 0.9700
C9 H9A . 0.9700
C9 H9B . 0.9700
C1 C6 . 1.383(4)
C1 H1 . 0.9300
C4 C5 . 1.356(5)
C4 H4 . 0.9300
C6 C5 . 1.380(5)
C6 H6 . 0.9300
C5 H5 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O1 3_666 0.802(10) 1.857(12) 2.634(2) 163(3)
N4 H4A O2 1_565 0.885(10) 2.41(2) 3.046(2) 129(2)
N4 H4B O3 1_565 0.887(10) 2.118(13) 2.973(2) 161(2)
C7 H7A O1 1_545 0.97 2.53 3.449(3) 158.1
C9 H9A N3 2_646 0.97 2.58 3.345(3) 136.0
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
N2 N1 C7 C8 -86.8(2)
C2 N1 C7 C8 82.4(3)
C3 N3 N2 N1 -0.6(3)
C2 N1 N2 N3 1.2(2)
C7 N1 N2 N3 172.31(19)
Cu O2 C8 O1 16.3(3)
Cu O2 C8 C7 -162.68(14)
N1 C7 C8 O1 -3.5(3)
N1 C7 C8 O2 175.61(17)
N2 N3 C3 C2 -0.2(3)
N2 N3 C3 C4 -179.3(3)
N2 N1 C2 C3 -1.2(2)
C7 N1 C2 C3 -171.29(19)
N2 N1 C2 C1 178.6(2)
C7 N1 C2 C1 8.5(4)
N3 C3 C2 N1 0.9(2)
C4 C3 C2 N1 -179.9(2)
N3 C3 C2 C1 -178.9(2)
C4 C3 C2 C1 0.3(3)
Cu N4 C9 C10 50.9(2)
O3 C10 C9 N4 -60.3(3)
N1 C2 C1 C6 179.8(2)
C3 C2 C1 C6 -0.4(3)
N3 C3 C4 C5 179.0(3)
C2 C3 C4 C5 -0.1(4)
C2 C1 C6 C5 0.4(4)
C3 C4 C5 C6 0.0(5)
C1 C6 C5 C4 -0.1(5)
