#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/10/2241037.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_2241037
loop_
_publ_author_name
'Tobón-Trujillo, Luis Manuel'
'Villanueva-Sánchez, Luis Felipe'
'Martínez-Otero, Diego'
'Dorazco-González, Alejandro'
_publ_section_title
;
 Crystal structure of
 bis(μ₂-tetrabromophthalato-κ²O¹:O²)bis[aqua(N,N,N',N'-tetramethylethane-1,2-diamine-κ²N,N')copper(II)]
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m171
_journal_page_last               m172
_journal_paper_doi               10.1107/S2056989015015194
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Cu2 (C8 Br4 O4)2 (C6 H16 N2)2 (H2 O)2]'
_chemical_formula_moiety         'C28 H36 Br8 Cu2 N4 O10'
_chemical_formula_sum            'C28 H36 Br8 Cu2 N4 O10'
_chemical_formula_weight         1354.97
_chemical_name_systematic
Bis(μ₂-tetrabromophthalato-κ²O¹:O²)bis[aqua(N,N,N',N'-tetramethylethane-1,2-diamine-κ²N,N')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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 95.4910(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0961(2)
_cell_length_b                   9.2281(2)
_cell_length_c                   24.4026(7)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.36
_cell_volume                     2038.95(9)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17394
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.324
_exptl_absorpt_coefficient_mu    8.937
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    2.207
_exptl_crystal_description       prism
_exptl_crystal_F_000             1300
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.411
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0162
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0162P)²+2.4857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0382
_refine_ls_wR_factor_ref         0.0387
_reflns_number_gt                3547
_reflns_number_total             3739
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xu5866sup1.cf
_cod_data_source_block           I
_cod_database_code               2241037
_cod_database_fobs_code          2241037
_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   0.210
_shelx_estimated_absorpt_t_max   0.521
_shelxl_version_number           2.013
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_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
Br Br1 0.34950(2) 0.30336(3) 0.71377(2) 0.01607(6) Uani d 1
Br Br2 0.62992(3) 0.47283(3) 0.78249(2) 0.02118(6) Uani d 1
Br Br3 0.95418(3) 0.47738(3) 0.73268(2) 0.01934(6) Uani d 1
Br Br4 1.00627(2) 0.27574(3) 0.62483(2) 0.01671(6) Uani d 1
Cu Cu1 0.32727(3) -0.12890(3) 0.55897(2) 0.01122(6) Uani d 1
O O1 0.45257(16) 0.02014(16) 0.59851(6) 0.0143(3) Uani d 1
O O2 0.32220(16) 0.22748(16) 0.58559(6) 0.0135(3) Uani d 1
O O3 0.65378(16) 0.19336(16) 0.52428(6) 0.0132(3) Uani d 1
O O4 0.79787(17) 0.02815(16) 0.57131(6) 0.0144(3) Uani d 1
O O5 0.17319(17) 0.01324(17) 0.53376(6) 0.0133(3) Uani d 1
H H5A 0.205(3) 0.091(2) 0.5454(10) 0.016 Uiso d 1
H H5B 0.179(3) 0.014(3) 0.5006(7) 0.016 Uiso d 1
N N1 0.4780(2) -0.2831(2) 0.58485(7) 0.0153(4) Uani d 1
N N2 0.1667(2) -0.2787(2) 0.57861(8) 0.0180(4) Uani d 1
C C1 0.5567(2) 0.2309(2) 0.63834(8) 0.0102(4) Uani d 1
C C2 0.5382(2) 0.3046(2) 0.68693(8) 0.0108(4) Uani d 1
C C3 0.6563(2) 0.3755(2) 0.71631(8) 0.0119(4) Uani d 1
C C4 0.7951(2) 0.3723(2) 0.69622(8) 0.0123(4) Uani d 1
C C5 0.8155(2) 0.2926(2) 0.64905(8) 0.0114(4) Uani d 1
C C6 0.6979(2) 0.2221(2) 0.62005(8) 0.0101(4) Uani d 1
C C7 0.4303(2) 0.1547(2) 0.60456(8) 0.0104(4) Uani d 1
C C8 0.7190(2) 0.1388(2) 0.56745(8) 0.0112(4) Uani d 1
C C9 0.3941(3) -0.4200(2) 0.57551(10) 0.0206(5) Uani d 1
H H9A 0.4525 -0.5017 0.5925 0.025 Uiso calc 1
H H9B 0.3757 -0.4388 0.5355 0.025 Uiso calc 1
C C10 0.2483(3) -0.4091(3) 0.60056(11) 0.0267(6) Uani d 1
H H10A 0.1885 -0.4970 0.5915 0.032 Uiso calc 1
H H10B 0.2665 -0.4022 0.6411 0.032 Uiso calc 1
C C11 0.6075(3) -0.2849(3) 0.55284(11) 0.0221(5) Uani d 1
H H11A 0.5747 -0.2979 0.5137 0.033 Uiso calc 1
H H11B 0.6728 -0.3651 0.5655 0.033 Uiso calc 1
H H11C 0.6611 -0.1931 0.5581 0.033 Uiso calc 1
C C12 0.5316(3) -0.2652(3) 0.64386(10) 0.0295(6) Uani d 1
H H12A 0.5925 -0.1776 0.6485 0.044 Uiso calc 1
H H12B 0.5908 -0.3497 0.6564 0.044 Uiso calc 1
H H12C 0.4470 -0.2564 0.6657 0.044 Uiso calc 1
C C13 0.0750(3) -0.2171(3) 0.61946(10) 0.0270(6) Uani d 1
H H13A 0.0211 -0.1327 0.6036 0.040 Uiso calc 1
H H13B 0.1384 -0.1874 0.6523 0.040 Uiso calc 1
H H13C 0.0045 -0.2903 0.6297 0.040 Uiso calc 1
C C14 0.0693(3) -0.3163(3) 0.52836(10) 0.0244(5) Uani d 1
H H14A 0.0251 -0.2277 0.5119 0.037 Uiso calc 1
H H14B -0.0091 -0.3815 0.5381 0.037 Uiso calc 1
H H14C 0.1275 -0.3644 0.5019 0.037 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'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_3
_geom_angle
O5 Cu1 O1 . 92.80(6)
O5 Cu1 N1 . 177.14(7)
O1 Cu1 N1 . 89.71(7)
O5 Cu1 N2 . 91.13(7)
O1 Cu1 N2 . 136.68(7)
N1 Cu1 N2 . 86.10(8)
O5 Cu1 O3 3_656 90.46(6)
O1 Cu1 O3 3_656 124.17(6)
N1 Cu1 O3 3_656 89.26(7)
N2 Cu1 O3 3_656 98.90(7)
C7 O1 Cu1 . 130.25(14)
C8 O3 Cu1 3_656 127.37(14)
C11 N1 C9 . 109.53(18)
C11 N1 C12 . 108.07(19)
C9 N1 C12 . 111.12(19)
C11 N1 Cu1 . 113.14(14)
C9 N1 Cu1 . 103.09(14)
C12 N1 Cu1 . 111.86(15)
C13 N2 C14 . 108.52(19)
C13 N2 C10 . 111.32(19)
C14 N2 C10 . 110.3(2)
C13 N2 Cu1 . 110.61(15)
C14 N2 Cu1 . 109.81(14)
C10 N2 Cu1 . 106.31(14)
C2 C1 C6 . 119.26(19)
C2 C1 C7 . 122.73(19)
C6 C1 C7 . 117.98(18)
C1 C2 C3 . 121.13(19)
C1 C2 Br1 . 118.64(16)
C3 C2 Br1 . 120.21(16)
C2 C3 C4 . 119.12(19)
C2 C3 Br2 . 120.61(16)
C4 C3 Br2 . 120.27(15)
C5 C4 C3 . 119.80(19)
C5 C4 Br3 . 120.18(16)
C3 C4 Br3 . 120.02(15)
C6 C5 C4 . 120.80(19)
C6 C5 Br4 . 119.17(16)
C4 C5 Br4 . 120.01(16)
C5 C6 C1 . 119.73(19)
C5 C6 C8 . 120.89(19)
C1 C6 C8 . 119.35(18)
O2 C7 O1 . 127.93(19)
O2 C7 C1 . 118.85(18)
O1 C7 C1 . 113.20(18)
O4 C8 O3 . 127.65(19)
O4 C8 C6 . 117.88(18)
O3 C8 C6 . 114.47(18)
N1 C9 C10 . 109.8(2)
N2 C10 C9 . 109.52(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C2 . 1.895(2)
Br2 C3 . 1.883(2)
Br3 C4 . 1.892(2)
Br4 C5 . 1.893(2)
Cu1 O5 . 1.9744(16)
Cu1 O1 . 1.9776(15)
Cu1 N1 . 2.0340(19)
Cu1 N2 . 2.0995(19)
Cu1 O3 3_656 2.1396(14)
O1 C7 . 1.269(3)
O2 C7 . 1.243(3)
O3 C8 . 1.263(3)
O3 Cu1 3_656 2.1396(14)
O4 C8 . 1.246(3)
N1 C11 . 1.475(3)
N1 C9 . 1.482(3)
N1 C12 . 1.485(3)
N2 C13 . 1.473(3)
N2 C14 . 1.484(3)
N2 C10 . 1.487(3)
C1 C2 . 1.391(3)
C1 C6 . 1.402(3)
C1 C7 . 1.521(3)
C2 C3 . 1.396(3)
C3 C4 . 1.398(3)
C4 C5 . 1.393(3)
C5 C6 . 1.387(3)
C6 C8 . 1.524(3)
C9 C10 . 1.516(3)
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
O5 H5A O2 . 0.81(2) 1.87(2) 2.649(2) 161(2)
O5 H5B O4 3_656 0.816(18) 1.829(18) 2.630(2) 167(3)
C10 H10A Br4 1_445 0.99 2.84 3.729(3) 150
C11 H11C O4 . 0.98 2.40 3.376(3) 179
C13 H13A O4 1_455 0.98 2.58 3.506(3) 158
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
C6 C1 C2 C3 . 3.0(3)
C7 C1 C2 C3 . -178.78(19)
C6 C1 C2 Br1 . -175.50(15)
C7 C1 C2 Br1 . 2.7(3)
C1 C2 C3 C4 . 0.2(3)
Br1 C2 C3 C4 . 178.71(15)
C1 C2 C3 Br2 . -179.24(15)
Br1 C2 C3 Br2 . -0.7(2)
C2 C3 C4 C5 . -3.3(3)
Br2 C3 C4 C5 . 176.09(16)
C2 C3 C4 Br3 . 176.10(15)
Br2 C3 C4 Br3 . -4.5(2)
C3 C4 C5 C6 . 3.3(3)
Br3 C4 C5 C6 . -176.16(16)
C3 C4 C5 Br4 . -175.18(16)
Br3 C4 C5 Br4 . 5.4(2)
C4 C5 C6 C1 . 0.0(3)
Br4 C5 C6 C1 . 178.46(15)
C4 C5 C6 C8 . 178.09(19)
Br4 C5 C6 C8 . -3.4(3)
C2 C1 C6 C5 . -3.1(3)
C7 C1 C6 C5 . 178.62(18)
C2 C1 C6 C8 . 178.75(18)
C7 C1 C6 C8 . 0.5(3)
Cu1 O1 C7 O2 . -1.5(3)
Cu1 O1 C7 C1 . -179.92(13)
C2 C1 C7 O2 . 60.4(3)
C6 C1 C7 O2 . -121.4(2)
C2 C1 C7 O1 . -121.0(2)
C6 C1 C7 O1 . 57.2(2)
Cu1 O3 C8 O4 3_656 -6.9(3)
Cu1 O3 C8 C6 3_656 172.16(13)
C5 C6 C8 O4 . 66.3(3)
C1 C6 C8 O4 . -115.6(2)
C5 C6 C8 O3 . -112.8(2)
C1 C6 C8 O3 . 65.3(3)
C11 N1 C9 C10 . -170.79(19)
C12 N1 C9 C10 . 69.9(2)
Cu1 N1 C9 C10 . -50.1(2)
C13 N2 C10 C9 . -148.7(2)
C14 N2 C10 C9 . 90.8(2)
Cu1 N2 C10 C9 . -28.2(2)
N1 C9 C10 N2 . 54.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168326392
