#------------------------------------------------------------------------------
#$Date: 2020-01-25 00:40:37 +0200 (Sat, 25 Jan 2020) $
#$Revision: 247208 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/73/4517342.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_4517342
loop_
_publ_author_name
'Kordestani, Nazanin'
'Rudbari, Hadi Amiri'
'Fernandes, Alexandra R.'
'Raposo, Luís R'
'Baptista, Pedro V.'
'Ferreira, Daniela'
'Bruno, Giuseppe'
'Bella, Giovanni'
'Scopelliti, Rosario'
'Braun, Jason D.'
'Herbert, David E.'
'Blacque, Olivier'
_publ_section_title
;
 Antiproliferative Activities of Diimine-Based Mixed Ligand Copper(II)
 Complexes.
;
_journal_name_full               'ACS combinatorial science'
_journal_paper_doi               10.1021/acscombsci.9b00202
_journal_year                    2020
_chemical_formula_sum            'C17 H11 Br Cl Cu N3 O5'
_chemical_formula_weight         516.19
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.212(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5010(6)
_cell_length_b                   12.0141(7)
_cell_length_c                   16.0425(9)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.62
_cell_volume                     1775.14(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_source         'fine--focus tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            48996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_min         2.619
_exptl_absorpt_coefficient_mu    3.669
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_description       block
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.428
_refine_diff_density_min         -0.941
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0447
_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)+(0.0283P)²+6.0726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3536
_reflns_number_total             4412
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            co9b00202_si_003.cif
_cod_data_source_block           har002_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4517342
_shelx_shelxl_version_number     2014/7
_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   0.315
_shelx_estimated_absorpt_t_max   0.867
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_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
Br1 Br 0.31916(5) -0.01914(3) -0.12571(3) 0.03631(12) Uani 1 1 d . . . A 43
C1 C 0.1009(5) 0.2688(3) -0.1261(3) 0.0338(9) Uani 1 1 d . . . A 43
H1 H 0.1724 0.2121 -0.1197 0.041 Uiso 1 1 calc R U . A 43
C2 C 0.0694(5) 0.3311(3) -0.2001(3) 0.0366(9) Uani 1 1 d . . . A 43
H2 H 0.1167 0.3169 -0.2448 0.044 Uiso 1 1 calc R U . A 43
C3 C -0.0328(5) 0.4149(4) -0.2083(3) 0.0363(9) Uani 1 1 d . . . A 43
H3 H -0.0563 0.4592 -0.2588 0.044 Uiso 1 1 calc R U . A 43
C4 C -0.1008(4) 0.4341(3) -0.1427(3) 0.0312(8) Uani 1 1 d . . . A 43
H4 H -0.1703 0.4920 -0.1471 0.037 Uiso 1 1 calc R U . A 43
C5 C -0.0653(4) 0.3669(3) -0.0704(2) 0.0232(7) Uani 1 1 d . . . A 43
C6 C -0.1319(4) 0.3751(3) 0.0039(2) 0.0246(7) Uani 1 1 d . . . A 43
C15 C 0.2888(4) -0.1420(3) 0.1454(3) 0.0290(8) Uani 1 1 d . . . A 43
H15 H 0.2802 -0.1691 0.1996 0.035 Uiso 1 1 calc R U . A 43
C7 C -0.2379(4) 0.4526(3) 0.0097(3) 0.0314(8) Uani 1 1 d . . . A 43
H7 H -0.2706 0.5059 -0.0346 0.038 Uiso 1 1 calc R U . A 43
C8 C -0.2942(5) 0.4503(3) 0.0808(3) 0.0362(9) Uani 1 1 d . . . A 43
H8 H -0.3681 0.5014 0.0856 0.043 Uiso 1 1 calc R U . A 43
C9 C -0.2432(5) 0.3735(3) 0.1453(3) 0.0339(9) Uani 1 1 d . . . A 43
H9 H -0.2806 0.3716 0.1951 0.041 Uiso 1 1 calc R U . A 43
C10 C -0.1367(4) 0.2995(3) 0.1360(2) 0.0287(8) Uani 1 1 d . . . A 43
H10 H -0.1005 0.2470 0.1803 0.034 Uiso 1 1 calc R U . A 43
C11 C 0.2202(4) -0.0049(3) 0.0268(2) 0.0245(7) Uani 1 1 d . . . A 43
C12 C 0.3089(4) -0.0673(3) -0.0150(2) 0.0277(8) Uani 1 1 d . . . A 43
C13 C 0.3881(4) -0.1587(3) 0.0216(3) 0.0310(8) Uani 1 1 d . . . A 43
H13 H 0.4492 -0.1969 -0.0077 0.037 Uiso 1 1 calc R U . A 43
C14 C 0.3769(4) -0.1942(3) 0.1026(3) 0.0321(9) Uani 1 1 d . . . A 43
C16 C 0.2099(4) -0.0465(3) 0.1082(2) 0.0252(7) Uani 1 1 d . . . A 43
C17 C 0.1191(4) 0.0054(3) 0.1558(2) 0.0268(8) Uani 1 1 d . . . A 43
H17 H 0.1073 -0.0326 0.2055 0.032 Uiso 1 1 calc R U . A 43
Cl1 Cl 0.47840(13) -0.31011(9) 0.14884(7) 0.0463(3) Uani 1 1 d . . . A 43
Cu1 Cu 0.06313(5) 0.19317(3) 0.04269(3) 0.02400(12) Uani 1 1 d . . . A 43
N1 N 0.0348(3) 0.2851(2) -0.0629(2) 0.0264(6) Uani 1 1 d . . . A 43
N2 N -0.0833(3) 0.2999(2) 0.06617(19) 0.0240(6) Uani 1 1 d . . . A 43
N3 N 0.3491(4) 0.3088(3) 0.1306(2) 0.0325(7) Uani 1 1 d . . . A 43
O1 O 0.1532(3) 0.0819(2) -0.01011(17) 0.0284(6) Uani 1 1 d . . . A 43
O2 O 0.0536(3) 0.0958(2) 0.13844(17) 0.0288(6) Uani 1 1 d . . . A 43
O3 O 0.2263(4) 0.3011(3) 0.1360(3) 0.0554(9) Uani 1 1 d . . . A 43
O4A O 0.3716(15) 0.281(2) 0.0615(15) 0.080(7) Uani 0.40(3) 1 d . . P B 1
O4B O 0.4045(10) 0.2233(11) 0.1048(10) 0.060(4) Uani 0.60(3) 1 d . . P B 2
O5 O 0.4292(4) 0.3871(3) 0.1672(2) 0.0478(8) 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'
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 122.4(4)
C1 C2 C3 118.5(4)
C4 C3 C2 119.9(4)
C3 C4 C5 118.5(4)
N1 C5 C4 121.3(3)
N1 C5 C6 114.0(3)
C4 C5 C6 124.7(3)
N2 C6 C7 121.6(3)
N2 C6 C5 114.6(3)
C7 C6 C5 123.8(3)
C14 C15 C16 119.2(4)
C8 C7 C6 118.5(4)
C7 C8 C9 120.0(4)
C10 C9 C8 118.6(4)
N2 C10 C9 121.8(4)
O1 C11 C12 119.7(3)
O1 C11 C16 124.7(3)
C12 C11 C16 115.6(3)
C13 C12 C11 123.1(4)
C13 C12 Br1 119.7(3)
C11 C12 Br1 117.2(3)
C12 C13 C14 118.8(4)
C15 C14 C13 121.8(3)
C15 C14 Cl1 119.7(3)
C13 C14 Cl1 118.5(3)
C15 C16 C11 121.4(3)
C15 C16 C17 117.1(3)
C11 C16 C17 121.5(3)
O2 C17 C16 126.5(3)
O1 Cu1 O2 92.42(11)
O1 Cu1 N1 89.56(12)
O2 Cu1 N1 169.50(12)
O1 Cu1 N2 161.81(12)
O2 Cu1 N2 93.86(11)
N1 Cu1 N2 81.32(12)
O1 Cu1 O3 112.73(12)
O2 Cu1 O3 88.82(13)
N1 Cu1 O3 99.93(14)
N2 Cu1 O3 84.47(12)
C1 N1 C5 119.5(3)
C1 N1 Cu1 125.3(3)
C5 N1 Cu1 115.1(2)
C10 N2 C6 119.6(3)
C10 N2 Cu1 125.5(3)
C6 N2 Cu1 114.9(2)
O3 N3 O5 120.8(4)
C11 O1 Cu1 126.3(2)
C17 O2 Cu1 125.4(2)
N3 O3 Cu1 121.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.893(4)
C1 N1 1.331(5)
C1 C2 1.373(6)
C2 C3 1.383(6)
C3 C4 1.382(6)
C4 C5 1.386(5)
C5 N1 1.352(5)
C5 C6 1.484(5)
C6 N2 1.342(5)
C6 C7 1.390(5)
C15 C14 1.359(6)
C15 C16 1.420(5)
C7 C8 1.374(6)
C8 C9 1.383(6)
C9 C10 1.382(5)
C10 N2 1.338(5)
C11 O1 1.287(4)
C11 C12 1.414(5)
C11 C16 1.424(5)
C12 C13 1.379(5)
C13 C14 1.397(6)
C14 Cl1 1.751(4)
C16 C17 1.428(5)
C17 O2 1.248(4)
Cu1 O1 1.896(2)
Cu1 O2 1.950(3)
Cu1 N1 1.985(3)
Cu1 N2 1.995(3)
Cu1 O3 2.278(3)
N3 O3 1.195(4)
N3 O5 1.260(5)
