#------------------------------------------------------------------------------
#$Date: 2017-04-05 13:02:21 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195148 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/60/7056007.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_7056007
loop_
_publ_author_name
'Cindrić, Marina'
'Bjelopetrović, Alen'
'Pavlović, Gordana'
'Damjanović, Vladimir'
'Lovrić, Jasna'
'Matković-Čalogović, Dubravka'
'Vrdoljak, Višnja'
_publ_section_title
;
 Copper(ii) complexes with benzhydrazone-related ligands: synthesis,
 structural studies and cytotoxicity assay
;
_journal_issue                   6
_journal_name_full               'New J. Chem.'
_journal_page_first              2425
_journal_paper_doi               10.1039/C6NJ03827A
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C19 H14 Cu N3 O2, C H4 O'
_chemical_formula_sum            'C20 H18 Cu N3 O3'
_chemical_formula_weight         411.91
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-05 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.746(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3899(3)
_cell_length_b                   7.9499(2)
_cell_length_c                   20.1358(5)
_cell_measurement_reflns_used    6887
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.0930
_cell_measurement_theta_min      4.4390
_cell_volume                     1796.95(8)
_computing_cell_refinement
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_data_collection
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_data_reduction
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17601
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         4.107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction using 
spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.519
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0378
_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)+(0.0514P)²+1.1931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4312
_reflns_number_total             4750
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6nj03827a2.cif
_cod_data_source_block           1bpy_2MeOH
_cod_depositor_comments
'Adding full bibliography for 7056006--7056012.cif.'
_cod_database_code               7056007
_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.
;
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
Cu1 Cu 0.96540(2) 0.20466(3) 0.99957(2) 0.01880(8) Uani 1 1 d . .
O1 O 0.97279(11) 0.34278(17) 1.07942(7) 0.0216(3) Uani 1 1 d . .
O2 O 0.98074(11) 0.06087(17) 0.92595(7) 0.0218(3) Uani 1 1 d . .
N2 N 1.15488(14) 0.4186(2) 1.05228(8) 0.0229(3) Uani 1 1 d . .
N1 N 1.11640(13) 0.31209(19) 0.99814(8) 0.0200(3) Uani 1 1 d . .
C17 C 0.56137(14) 0.0305(2) 0.99921(9) 0.0193(3) Uani 1 1 d . .
C10 C 1.05739(16) 0.0785(2) 0.88404(9) 0.0208(3) Uani 1 1 d . .
N3 N 0.79417(13) 0.1423(2) 0.99680(8) 0.0201(3) Uani 1 1 d . .
C8 C 1.18185(16) 0.3001(2) 0.95198(10) 0.0225(4) Uani 1 1 d . .
H8 H 1.2515 0.3677 0.9562 0.027 Uiso 1 1 calc R U
C9 C 1.15568(16) 0.1902(2) 0.89425(10) 0.0223(4) Uani 1 1 d . .
C3 C 1.01918(17) 0.5158(3) 1.20038(10) 0.0266(4) Uani 1 1 d . .
H3 H 0.9513 0.4446 1.1917 0.032 Uiso 1 1 calc R U
C16 C 0.61997(16) 0.1387(3) 1.04861(10) 0.0262(4) Uani 1 1 d . .
H16 H 0.5810 0.1766 1.0840 0.031 Uiso 1 1 calc R U
C7 C 1.19546(18) 0.6326(3) 1.16717(10) 0.0272(4) Uani 1 1 d . .
H7 H 1.2486 0.6415 1.1357 0.033 Uiso 1 1 calc R U
C19 C 0.73787(16) 0.0406(2) 0.94851(10) 0.0227(4) Uani 1 1 d . .
H19 H 0.7783 0.0065 0.9132 0.027 Uiso 1 1 calc R U
C18 C 0.62310(15) -0.0163(2) 0.94829(10) 0.0229(4) Uani 1 1 d . .
H18 H 0.5862 -0.0880 0.9131 0.028 Uiso 1 1 calc R U
C14 C 1.23490(19) 0.1936(3) 0.84730(11) 0.0300(4) Uani 1 1 d . .
H14 H 1.3006 0.2689 0.8544 0.036 Uiso 1 1 calc R U
C1 C 1.07270(15) 0.4226(2) 1.09139(9) 0.0199(3) Uani 1 1 d . .
C2 C 1.09683(15) 0.5255(2) 1.15385(9) 0.0216(3) Uani 1 1 d . .
C12 C 1.1223(2) -0.0191(3) 0.78139(11) 0.0331(4) Uani 1 1 d . .
H12 H 1.1109 -0.0913 0.7432 0.040 Uiso 1 1 calc R U
C11 C 1.04307(17) -0.0241(3) 0.82599(10) 0.0258(4) Uani 1 1 d . .
H11 H 0.9770 -0.0986 0.8175 0.031 Uiso 1 1 calc R U
C13 C 1.2194(2) 0.0912(3) 0.79167(11) 0.0360(5) Uani 1 1 d . .
H13 H 1.2737 0.0951 0.7607 0.043 Uiso 1 1 calc R U
C6 C 1.2157(2) 0.7257(3) 1.22617(12) 0.0341(5) Uani 1 1 d . .
H6 H 1.2831 0.7977 1.2352 0.041 Uiso 1 1 calc R U
C15 C 0.73480(16) 0.1905(2) 1.04585(10) 0.0252(4) Uani 1 1 d . .
H15 H 0.7735 0.2634 1.0801 0.030 Uiso 1 1 calc R U
C5 C 1.1384(2) 0.7142(3) 1.27205(11) 0.0363(5) Uani 1 1 d . .
H5 H 1.1527 0.7784 1.3124 0.044 Uiso 1 1 calc R U
C4 C 1.0405(2) 0.6095(3) 1.25917(11) 0.0343(5) Uani 1 1 d . .
H4 H 0.9876 0.6016 1.2908 0.041 Uiso 1 1 calc R U
O3 O 1.40696(14) 0.4029(2) 1.07705(11) 0.0455(4) Uani 1 1 d D .
H3O H 1.3349(17) 0.422(4) 1.0732(16) 0.055 Uiso 1 1 d D U
C20 C 1.4751(2) 0.5465(3) 1.09047(16) 0.0483(6) Uani 1 1 d . .
H20A H 1.4642 0.5927 1.1341 0.072 Uiso 1 1 calc R U
H20B H 1.4501 0.6300 1.0551 0.072 Uiso 1 1 calc R U
H20C H 1.5592 0.5187 1.0917 0.072 Uiso 1 1 calc R U
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'
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_3
O2 Cu1 N1 93.14(6) .
O2 Cu1 O1 171.95(5) .
N1 Cu1 O1 81.23(6) .
O2 Cu1 N3 92.69(6) .
N1 Cu1 N3 167.75(7) .
O1 Cu1 N3 93.94(6) .
C1 O1 Cu1 110.30(11) .
C10 O2 Cu1 126.28(12) .
C1 N2 N1 108.71(14) .
C8 N1 N2 117.76(15) .
C8 N1 Cu1 127.23(13) .
N2 N1 Cu1 114.96(11) .
C18 C17 C16 116.78(15) .
C18 C17 C17 121.6(2) 3_657
C16 C17 C17 121.6(2) 3_657
O2 C10 C11 118.12(16) .
O2 C10 C9 124.45(17) .
C11 C10 C9 117.39(17) .
C19 N3 C15 117.81(15) .
C19 N3 Cu1 120.86(12) .
C15 N3 Cu1 121.15(12) .
N1 C8 C9 123.98(16) .
N1 C8 H8 118.0 .
C9 C8 H8 118.0 .
C14 C9 C10 119.58(18) .
C14 C9 C8 117.28(17) .
C10 C9 C8 123.12(17) .
C4 C3 C2 120.33(19) .
C4 C3 H3 119.8 .
C2 C3 H3 119.8 .
C15 C16 C17 119.78(17) .
C15 C16 H16 120.1 .
C17 C16 H16 120.1 .
C6 C7 C2 120.1(2) .
C6 C7 H7 120.0 .
C2 C7 H7 120.0 .
N3 C19 C18 122.37(17) .
N3 C19 H19 118.8 .
C18 C19 H19 118.8 .
C19 C18 C17 120.42(17) .
C19 C18 H18 119.8 .
C17 C18 H18 119.8 .
C13 C14 C9 121.74(19) .
C13 C14 H14 119.1 .
C9 C14 H14 119.1 .
O1 C1 N2 124.64(16) .
O1 C1 C2 117.37(16) .
N2 C1 C2 117.99(16) .
C3 C2 C7 118.98(18) .
C3 C2 C1 119.37(16) .
C7 C2 C1 121.64(17) .
C11 C12 C13 120.71(19) .
C11 C12 H12 119.6 .
C13 C12 H12 119.6 .
C12 C11 C10 121.75(18) .
C12 C11 H11 119.1 .
C10 C11 H11 119.1 .
C14 C13 C12 118.82(19) .
C14 C13 H13 120.6 .
C12 C13 H13 120.6 .
C5 C6 C7 120.4(2) .
C5 C6 H6 119.8 .
C7 C6 H6 119.8 .
N3 C15 C16 122.83(17) .
N3 C15 H15 118.6 .
C16 C15 H15 118.6 .
C4 C5 C6 120.0(2) .
C4 C5 H5 120.0 .
C6 C5 H5 120.0 .
C5 C4 C3 120.3(2) .
C5 C4 H4 119.9 .
C3 C4 H4 119.9 .
C20 O3 H3O 112(2) .
O3 C20 H20A 109.5 .
O3 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
O3 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.9032(13) .
Cu1 N1 1.9248(15) .
Cu1 O1 1.9371(13) .
Cu1 N3 2.0040(15) .
O1 C1 1.289(2) .
O2 C10 1.321(2) .
N2 C1 1.322(2) .
N2 N1 1.391(2) .
N1 C8 1.290(2) .
C17 C18 1.389(3) .
C17 C16 1.396(3) .
C17 C17 1.485(3) 3_657
C10 C11 1.412(3) .
C10 C9 1.416(3) .
N3 C19 1.341(2) .
N3 C15 1.344(2) .
C8 C9 1.445(3) .
C8 H8 0.9500 .
C9 C14 1.413(3) .
C3 C4 1.385(3) .
C3 C2 1.395(3) .
C3 H3 0.9500 .
C16 C15 1.381(3) .
C16 H16 0.9500 .
C7 C6 1.385(3) .
C7 C2 1.399(3) .
C7 H7 0.9500 .
C19 C18 1.383(2) .
C19 H19 0.9500 .
C18 H18 0.9500 .
C14 C13 1.372(3) .
C14 H14 0.9500 .
C1 C2 1.486(2) .
C12 C11 1.378(3) .
C12 C13 1.399(3) .
C12 H12 0.9500 .
C11 H11 0.9500 .
C13 H13 0.9500 .
C6 C5 1.383(4) .
C6 H6 0.9500 .
C15 H15 0.9500 .
C5 C4 1.381(3) .
C5 H5 0.9500 .
C4 H4 0.9500 .
O3 C20 1.381(3) .
O3 H3O 0.826(18) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
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
C1 N2 N1 C8 175.78(16) .
C1 N2 N1 Cu1 -1.91(18) .
Cu1 O2 C10 C11 -169.86(13) .
Cu1 O2 C10 C9 12.2(3) .
N2 N1 C8 C9 177.61(16) .
Cu1 N1 C8 C9 -5.0(3) .
O2 C10 C9 C14 177.41(18) .
C11 C10 C9 C14 -0.6(3) .
O2 C10 C9 C8 -1.0(3) .
C11 C10 C9 C8 -178.98(17) .
N1 C8 C9 C14 178.80(18) .
N1 C8 C9 C10 -2.8(3) .
C18 C17 C16 C15 -1.4(3) .
C17 C17 C16 C15 179.0(2) 3_657
C15 N3 C19 C18 -0.8(3) .
Cu1 N3 C19 C18 174.43(15) .
N3 C19 C18 C17 -0.2(3) .
C16 C17 C18 C19 1.2(3) .
C17 C17 C18 C19 -179.2(2) 3_657
C10 C9 C14 C13 0.0(3) .
C8 C9 C14 C13 178.4(2) .
Cu1 O1 C1 N2 3.9(2) .
Cu1 O1 C1 C2 -175.76(12) .
N1 N2 C1 O1 -1.4(2) .
N1 N2 C1 C2 178.25(14) .
C4 C3 C2 C7 -0.8(3) .
C4 C3 C2 C1 179.45(18) .
C6 C7 C2 C3 0.7(3) .
C6 C7 C2 C1 -179.49(18) .
O1 C1 C2 C3 7.7(2) .
N2 C1 C2 C3 -171.98(17) .
O1 C1 C2 C7 -172.04(17) .
N2 C1 C2 C7 8.3(3) .
C13 C12 C11 C10 -1.1(3) .
O2 C10 C11 C12 -176.94(18) .
C9 C10 C11 C12 1.2(3) .
C9 C14 C13 C12 0.1(3) .
C11 C12 C13 C14 0.5(4) .
C2 C7 C6 C5 -0.4(3) .
C19 N3 C15 C16 0.6(3) .
Cu1 N3 C15 C16 -174.58(16) .
C17 C16 C15 N3 0.5(3) .
C7 C6 C5 C4 0.1(4) .
C6 C5 C4 C3 -0.1(3) .
C2 C3 C4 C5 0.5(3) .
