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#$Date: 2021-01-06 05:08:25 +0200 (Wed, 06 Jan 2021) $
#$Revision: 260554 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/02/7060249.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_7060249
loop_
_publ_author_name
'Zahmati Eraj, Malihe'
'Eriksson, Lars'
'Alibolandi, Mona'
'Babaei, Maryam'
'Saljooghi, Amir Sh.'
'Ramezani, Mohammad'
_publ_section_title
;
 Synthesis, X-ray structure, antiproliferative activity, interaction with
 HSA and docking studies of three novel mono and binuclear copper
 complexes containing the maltol ligand
;
_journal_issue                   46
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20101
_journal_page_last               20114
_journal_paper_doi               10.1039/D0NJ03552A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C16 H13 Br2 Cu N2 O4, N O3'
_chemical_formula_sum            'C16 H13 Br2 Cu N3 O7'
_chemical_formula_weight         582.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-09-29 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.906(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1803(2)
_cell_length_b                   11.3573(2)
_cell_length_c                   15.1698(3)
_cell_measurement_reflns_used    12196
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.5920
_cell_measurement_theta_min      3.3140
_cell_volume                     1919.17(6)
_computing_cell_refinement       'CrysAlisPro, (Rigaku, 2017)'
_computing_data_collection       'CrysAlisPro, (Rigaku, 2017)'
_computing_data_reduction        'CrysAlisPro, (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.5467
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω and φ scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43533
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.238
_exptl_absorpt_coefficient_mu    5.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_description       block
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.085
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0480
_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)+(0.0558P)²+6.4601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3553
_reflns_number_total             3918
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj03552a2.cif
_cod_data_source_block           r
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7060249
_shelx_shelxl_version_number     2016/6
_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.59775(5) 0.48208(5) 0.22509(4) 0.03570(18) Uani 1 1 d . . . . .
C2 C 0.3965(6) 0.7460(6) 0.0147(4) 0.0622(17) Uani 1 1 d . . . . .
H2A H 0.418165 0.757416 -0.044564 0.093 Uiso 1 1 calc R U . . .
H2B H 0.458828 0.776480 0.055898 0.093 Uiso 1 1 calc R U . . .
H2C H 0.322741 0.786755 0.022134 0.093 Uiso 1 1 calc R U . . .
C3 C 0.3809(5) 0.6220(6) 0.0308(4) 0.0481(13) Uani 1 1 d . . . . .
C4 C 0.4406(4) 0.5560(6) 0.0966(3) 0.0426(12) Uani 1 1 d . . . . .
C5 C 0.4145(4) 0.4366(6) 0.1057(3) 0.0462(13) Uani 1 1 d . . . . .
C6 C 0.3257(5) 0.3853(6) 0.0422(4) 0.0520(14) Uani 1 1 d . . . . .
H6 H 0.305904 0.305956 0.044786 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2744(5) 0.4531(8) -0.0185(4) 0.0649(19) Uani 1 1 d . . . . .
H7 H 0.217092 0.419372 -0.058839 0.078 Uiso 1 1 calc R U . . .
O8 O 0.2976(3) 0.5686(4) -0.0278(2) 0.0540(10) Uani 1 1 d . . . . .
O9 O 0.5248(3) 0.6054(4) 0.1542(2) 0.0467(9) Uani 1 1 d . . . . .
O10 O 0.4721(3) 0.3810(4) 0.1671(3) 0.0514(10) Uani 1 1 d . . . . .
O11 O 0.5142(4) 0.5208(5) 0.3548(3) 0.0565(11) Uani 1 1 d D . . . .
H11A H 0.551(6) 0.525(7) 0.400(4) 0.085 Uiso 1 1 d D U . . .
H11B H 0.457(5) 0.487(7) 0.365(4) 0.085 Uiso 1 1 d D U . . .
N12 N 0.7515(4) 0.5886(5) 0.5645(3) 0.0519(12) Uani 1 1 d . . . . .
O13 O 0.8458(5) 0.6348(7) 0.5514(5) 0.111(2) Uani 1 1 d . . . . .
O14 O 0.7291(8) 0.5674(7) 0.6386(4) 0.124(3) Uani 1 1 d . . . . .
O15 O 0.6785(7) 0.5705(8) 0.5048(6) 0.143(3) Uani 1 1 d . . . . .
N16 N 0.7024(3) 0.3481(4) 0.2655(2) 0.0326(8) Uani 1 1 d . . . . .
C17 C 0.6765(4) 0.2342(4) 0.2518(3) 0.0374(10) Uani 1 1 d . . . . .
H17 H 0.603275 0.214046 0.221856 0.045 Uiso 1 1 calc R U . . .
C18 C 0.7547(4) 0.1457(4) 0.2808(3) 0.0375(10) Uani 1 1 d . . . . .
H18 H 0.736631 0.066970 0.269139 0.045 Uiso 1 1 calc R U . . .
C19 C 0.8604(4) 0.1782(4) 0.3274(3) 0.0338(10) Uani 1 1 d . . . . .
C20 C 0.8896(4) 0.2951(4) 0.3416(3) 0.0325(9) Uani 1 1 d . . . . .
H20 H 0.961539 0.316862 0.372686 0.039 Uiso 1 1 calc R U . . .
C21 C 0.8080(4) 0.3787(4) 0.3080(3) 0.0297(9) Uani 1 1 d . . . . .
C22 C 0.8304(4) 0.5065(4) 0.3131(3) 0.0302(9) Uani 1 1 d . . . . .
C23 C 0.9320(4) 0.5580(4) 0.3555(3) 0.0337(10) Uani 1 1 d . . . . .
H23 H 0.991471 0.513054 0.385947 0.040 Uiso 1 1 calc R U . . .
C24 C 0.9411(4) 0.6795(4) 0.3504(3) 0.0371(10) Uani 1 1 d . . . . .
C25 C 0.8543(5) 0.7457(4) 0.3035(4) 0.0435(12) Uani 1 1 d . . . . .
H25 H 0.862446 0.826857 0.298133 0.052 Uiso 1 1 calc R U . . .
C26 C 0.7556(5) 0.6882(5) 0.2649(4) 0.0441(12) Uani 1 1 d . . . . .
H26 H 0.695253 0.732126 0.234441 0.053 Uiso 1 1 calc R U . . .
N27 N 0.7427(3) 0.5722(3) 0.2693(3) 0.0338(8) Uani 1 1 d . . . . .
Br1 Br 0.96541(5) 0.05877(5) 0.37247(4) 0.05055(19) Uani 1 1 d . . . . .
Br2 Br 1.07666(5) 0.75376(5) 0.40813(4) 0.0529(2) Uani 1 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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O9 Cu1 O10 85.49(17) . . ?
O9 Cu1 N16 161.86(16) . . ?
O10 Cu1 N16 94.03(16) . . ?
O9 Cu1 N27 96.31(16) . . ?
O10 Cu1 N27 170.24(17) . . ?
N16 Cu1 N27 81.26(15) . . ?
O9 Cu1 O11 99.05(17) . . ?
O10 Cu1 O11 99.68(17) . . ?
N16 Cu1 O11 98.91(17) . . ?
N27 Cu1 O11 89.53(17) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O8 C3 C4 119.3(6) . . ?
O8 C3 C2 114.0(5) . . ?
C4 C3 C2 126.6(6) . . ?
O9 C4 C3 120.8(6) . . ?
O9 C4 C5 118.7(5) . . ?
C3 C4 C5 120.5(5) . . ?
O10 C5 C4 117.5(5) . . ?
O10 C5 C6 124.8(6) . . ?
C4 C5 C6 117.6(5) . . ?
C7 C6 C5 118.1(6) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 O8 125.2(6) . . ?
C6 C7 H7 117.4 . . ?
O8 C7 H7 117.4 . . ?
C7 O8 C3 119.3(5) . . ?
C4 O9 Cu1 107.5(3) . . ?
C5 O10 Cu1 109.9(4) . . ?
Cu1 O11 H11A 123(6) . . ?
Cu1 O11 H11B 118(6) . . ?
H11A O11 H11B 104.3(19) . . ?
O15 N12 O14 119.9(8) . . ?
O15 N12 O13 120.2(7) . . ?
O14 N12 O13 119.8(7) . . ?
C17 N16 C21 119.7(4) . . ?
C17 N16 Cu1 125.4(3) . . ?
C21 N16 Cu1 114.9(3) . . ?
N16 C17 C18 122.1(4) . . ?
N16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C19 C18 C17 117.5(4) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 C20 121.4(4) . . ?
C18 C19 Br1 118.4(4) . . ?
C20 C19 Br1 120.3(4) . . ?
C19 C20 C21 117.6(4) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
N16 C21 C20 121.6(4) . . ?
N16 C21 C22 114.8(4) . . ?
C20 C21 C22 123.6(4) . . ?
N27 C22 C23 121.5(4) . . ?
N27 C22 C21 113.7(4) . . ?
C23 C22 C21 124.7(4) . . ?
C22 C23 C24 117.2(4) . . ?
C22 C23 H23 121.4 . . ?
C24 C23 H23 121.4 . . ?
C25 C24 C23 121.3(4) . . ?
C25 C24 Br2 120.0(4) . . ?
C23 C24 Br2 118.7(4) . . ?
C26 C25 C24 117.8(5) . . ?
C26 C25 H25 121.1 . . ?
C24 C25 H25 121.1 . . ?
N27 C26 C25 122.6(5) . . ?
N27 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C26 N27 C22 119.5(4) . . ?
C26 N27 Cu1 125.7(3) . . ?
C22 N27 Cu1 114.6(3) . . ?
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
Cu1 O9 1.906(4) . ?
Cu1 O10 1.962(4) . ?
Cu1 N16 1.985(4) . ?
Cu1 N27 1.985(4) . ?
Cu1 O11 2.291(4) . ?
C2 C3 1.442(9) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 O8 1.372(7) . ?
C3 C4 1.376(7) . ?
C4 O9 1.349(6) . ?
C4 C5 1.396(9) . ?
C5 O10 1.257(7) . ?
C5 C6 1.446(7) . ?
C6 C7 1.295(9) . ?
C6 H6 0.9300 . ?
C7 O8 1.347(9) . ?
C7 H7 0.9300 . ?
O11 H11A 0.77(5) . ?
O11 H11B 0.77(5) . ?
N12 O15 1.184(7) . ?
N12 O14 1.197(7) . ?
N12 O13 1.210(7) . ?
N16 C17 1.338(6) . ?
N16 C21 1.342(6) . ?
C17 C18 1.379(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(7) . ?
C19 Br1 1.883(5) . ?
C20 C21 1.384(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.473(6) . ?
C22 N27 1.359(6) . ?
C22 C23 1.386(6) . ?
C23 C24 1.386(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(7) . ?
C24 Br2 1.883(5) . ?
C25 C26 1.370(7) . ?
C25 H25 0.9300 . ?
C26 N27 1.328(7) . ?
C26 H26 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 Br1 0.93 2.93 3.703(6) 141.9 4_465
O11 H11A O15 0.77(5) 2.11(5) 2.856(7) 164(7) .
O11 H11B O14 0.77(5) 2.17(5) 2.909(10) 161(8) 3_666
C17 H17 O10 0.93 2.50 3.025(6) 116.3 .
C18 H18 O14 0.93 2.50 3.237(8) 136.9 4_565
C20 H20 O13 0.93 2.42 3.346(7) 176.7 3_766
C23 H23 O13 0.93 2.60 3.516(8) 170.7 3_766
C25 H25 Br1 0.93 3.05 3.880(5) 149.2 1_565
C26 H26 O9 0.93 2.61 3.103(6) 114.0 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O8 C3 C4 O9 178.7(4) . . . . ?
C2 C3 C4 O9 -0.8(8) . . . . ?
O8 C3 C4 C5 -2.0(8) . . . . ?
C2 C3 C4 C5 178.5(6) . . . . ?
O9 C4 C5 O10 -0.6(7) . . . . ?
C3 C4 C5 O10 180.0(5) . . . . ?
O9 C4 C5 C6 -178.8(4) . . . . ?
C3 C4 C5 C6 1.8(7) . . . . ?
O10 C5 C6 C7 -179.0(6) . . . . ?
C4 C5 C6 C7 -1.0(8) . . . . ?
C5 C6 C7 O8 0.4(10) . . . . ?
C6 C7 O8 C3 -0.6(9) . . . . ?
C4 C3 O8 C7 1.3(8) . . . . ?
C2 C3 O8 C7 -179.1(5) . . . . ?
C3 C4 O9 Cu1 -173.5(4) . . . . ?
C5 C4 O9 Cu1 7.1(5) . . . . ?
C4 C5 O10 Cu1 -6.1(6) . . . . ?
C6 C5 O10 Cu1 172.0(4) . . . . ?
C21 N16 C17 C18 0.6(7) . . . . ?
Cu1 N16 C17 C18 179.0(4) . . . . ?
N16 C17 C18 C19 2.1(7) . . . . ?
C17 C18 C19 C20 -2.7(7) . . . . ?
C17 C18 C19 Br1 177.1(4) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
Br1 C19 C20 C21 -179.1(3) . . . . ?
C17 N16 C21 C20 -2.8(7) . . . . ?
Cu1 N16 C21 C20 178.7(3) . . . . ?
C17 N16 C21 C22 175.6(4) . . . . ?
Cu1 N16 C21 C22 -3.0(5) . . . . ?
C19 C20 C21 N16 2.1(7) . . . . ?
C19 C20 C21 C22 -176.0(4) . . . . ?
N16 C21 C22 N27 -3.6(6) . . . . ?
C20 C21 C22 N27 174.7(4) . . . . ?
N16 C21 C22 C23 178.5(4) . . . . ?
C20 C21 C22 C23 -3.2(7) . . . . ?
N27 C22 C23 C24 -0.7(7) . . . . ?
C21 C22 C23 C24 177.0(4) . . . . ?
C22 C23 C24 C25 -1.6(7) . . . . ?
C22 C23 C24 Br2 179.2(3) . . . . ?
C23 C24 C25 C26 2.8(8) . . . . ?
Br2 C24 C25 C26 -178.0(4) . . . . ?
C24 C25 C26 N27 -1.8(9) . . . . ?
C25 C26 N27 C22 -0.4(8) . . . . ?
C25 C26 N27 Cu1 174.3(4) . . . . ?
C23 C22 N27 C26 1.7(7) . . . . ?
C21 C22 N27 C26 -176.3(4) . . . . ?
C23 C22 N27 Cu1 -173.6(3) . . . . ?
C21 C22 N27 Cu1 8.4(5) . . . . ?
