#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:34:12 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272659 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/90/7709050.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_7709050
loop_
_publ_author_name
'Stevanović, Nevena'
'Zlatar, Matija'
'Novaković, Irena'
'Pevec, Andrej'
'Radanović, Dušanka'
'Matić, Ivana Z'
'Đorđić Crnogorac, Marija'
'Stanojković, Tatjana'
'Vujčić, Miroslava'
'Gruden, Maja'
'Sladić, Dušan'
'Anđelković, Katarina'
'Turel, Iztok'
'Čobeljić, Božidar'
_publ_section_title
;
 Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary
 ammonium moiety: synthesis, experimental and theoretical characterization
 and cytotoxic activity.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              185
_journal_page_last               196
_journal_paper_doi               10.1039/d1dt03169d
_journal_volume                  51
_journal_year                    2021
_chemical_formula_sum            'C11 H20 B Cu F4 N7 O2 S'
_chemical_formula_weight         464.75
_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-2018/3
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.242(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0033(3)
_cell_length_b                   10.8941(3)
_cell_length_c                   25.6059(9)
_cell_measurement_reflns_used    8107
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.1670
_cell_measurement_theta_min      3.4380
_cell_volume                     1938.01(12)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17559
_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         27.485
_diffrn_reflns_theta_min         2.941
_exptl_absorpt_coefficient_mu    1.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis PRO; Oxford Diffraction, 2009'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       prism
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+0.9688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3789
_reflns_number_total             4425
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt03169d2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7709050--7709052.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7709050
_shelx_shelxl_version_number     2018/3
_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   0.511
_shelx_estimated_absorpt_t_max   0.782
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
Cu1 Cu 0.20037(5) 0.46833(3) 0.04197(2) 0.04201(12) Uani 1 1 d . . . . .
S1 S 0.23718(11) 0.06752(6) 0.02448(4) 0.0611(2) Uani 1 1 d . . . . .
O1 O 0.1064(3) 0.59420(15) 0.08771(7) 0.0440(4) Uani 1 1 d . . . . .
N1 N 0.2427(3) 0.2985(2) 0.01110(9) 0.0450(5) Uani 1 1 d . . . . .
N2 N 0.1327(3) 0.36770(17) 0.09879(8) 0.0381(4) Uani 1 1 d . . . . .
N3 N 0.0780(3) 0.42658(18) 0.14212(8) 0.0415(4) Uani 1 1 d . . . . .
N4 N 0.1596(3) 0.72306(18) 0.19065(9) 0.0466(5) Uani 1 1 d . . . . .
N5 N 0.2435(4) 0.5720(2) -0.01614(9) 0.0520(6) Uani 1 1 d . . . . .
N6 N 0.2422(3) 0.6828(2) -0.01303(9) 0.0459(5) Uani 1 1 d . . . . .
N7 N 0.2394(4) 0.7866(2) -0.01306(13) 0.0704(8) Uani 1 1 d . . . . .
C1 C 0.2945(4) 0.2480(3) -0.03385(11) 0.0565(7) Uani 1 1 d . . . . .
H1 H 0.324219 0.294457 -0.062203 0.068 Uiso 1 1 calc R U . . .
C2 C 0.2986(4) 0.1226(3) -0.03316(13) 0.0657(9) Uani 1 1 d . . . . .
H2 H 0.330772 0.073994 -0.060596 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2066(3) 0.2139(2) 0.04513(11) 0.0444(6) Uani 1 1 d . . . . .
C4 C 0.1393(3) 0.2490(2) 0.09495(10) 0.0411(5) Uani 1 1 d . . . . .
C5 C 0.0840(5) 0.1594(3) 0.13387(14) 0.0630(8) Uani 1 1 d . . . . .
H5A H 0.028762 0.202194 0.161124 0.095 Uiso 1 1 calc R U . . .
H5B H 0.195997 0.115182 0.149030 0.095 Uiso 1 1 calc R U . . .
H5C H -0.008611 0.102910 0.116695 0.095 Uiso 1 1 calc R U . . .
C6 C 0.0709(3) 0.5449(2) 0.13063(10) 0.0392(5) Uani 1 1 d . . . . .
C7 C 0.0108(4) 0.6261(2) 0.17310(10) 0.0451(6) Uani 1 1 d . . . . .
H7A H -0.010638 0.575999 0.203124 0.054 Uiso 1 1 calc R U . . .
H7B H -0.109846 0.665899 0.160175 0.054 Uiso 1 1 calc R U . . .
C8 C 0.3542(4) 0.6660(3) 0.20328(15) 0.0667(9) Uani 1 1 d . . . . .
H8A H 0.396023 0.634299 0.171627 0.100 Uiso 1 1 calc R U . . .
H8B H 0.347547 0.600326 0.227976 0.100 Uiso 1 1 calc R U . . .
H8C H 0.444058 0.726783 0.218341 0.100 Uiso 1 1 calc R U . . .
C9 C 0.1624(5) 0.8209(3) 0.14928(14) 0.0659(8) Uani 1 1 d . . . . .
H9A H 0.253555 0.883307 0.161827 0.099 Uiso 1 1 calc R U . . .
H9B H 0.036645 0.856615 0.141870 0.099 Uiso 1 1 calc R U . . .
H9C H 0.198896 0.785076 0.117732 0.099 Uiso 1 1 calc R U . . .
C10 C 0.1041(6) 0.7822(3) 0.23965(13) 0.0689(9) Uani 1 1 d . . . . .
H10A H 0.200962 0.840475 0.252941 0.103 Uiso 1 1 calc R U . . .
H10B H 0.092909 0.720301 0.265788 0.103 Uiso 1 1 calc R U . . .
H10C H -0.017130 0.823448 0.231481 0.103 Uiso 1 1 calc R U . . .
O2 O 0.5288(3) 0.4835(2) 0.09579(10) 0.0655(6) Uani 1 1 d . . . . .
H2A H 0.597717 0.476524 0.072345 0.098 Uiso 1 1 calc R U . . .
C11 C 0.5868(5) 0.3947(4) 0.13691(16) 0.0807(11) Uani 1 1 d . . . . .
H11A H 0.704960 0.420925 0.156912 0.121 Uiso 1 1 calc R U . . .
H11B H 0.605428 0.316172 0.121344 0.121 Uiso 1 1 calc R U . . .
H11C H 0.488454 0.388344 0.159715 0.121 Uiso 1 1 calc R U . . .
B1 B 0.6482(6) 0.9975(4) 0.18740(18) 0.0661(9) Uani 1 1 d . . . . .
F1A F 0.4859(10) 0.9962(10) 0.2109(4) 0.089(3) Uani 0.59(2) 1 d . . P A 1
F2A F 0.6829(13) 0.8756(8) 0.1707(5) 0.104(3) Uani 0.59(2) 1 d . . P A 1
F3A F 0.6041(18) 1.0611(10) 0.1409(3) 0.120(3) Uani 0.59(2) 1 d . . P A 1
F4A F 0.8087(18) 1.0302(11) 0.2167(6) 0.113(3) Uani 0.59(2) 1 d . . P A 1
F1B F 0.542(4) 0.954(3) 0.2247(9) 0.170(9) Uani 0.41(2) 1 d . . P A 2
F2B F 0.697(3) 0.913(2) 0.1595(7) 0.151(7) Uani 0.41(2) 1 d . . P A 2
F3B F 0.556(4) 1.0791(19) 0.1603(14) 0.212(11) Uani 0.41(2) 1 d . . P A 2
F4B F 0.785(3) 1.071(2) 0.2166(7) 0.123(7) Uani 0.41(2) 1 d . . P A 2
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cu1 N2 174.81(10) . . ?
N5 Cu1 O1 98.51(9) . . ?
N2 Cu1 O1 79.33(8) . . ?
N5 Cu1 N1 100.81(9) . . ?
N2 Cu1 N1 80.73(9) . . ?
O1 Cu1 N1 159.05(9) . . ?
C2 S1 C3 89.68(15) . . ?
C6 O1 Cu1 109.59(15) . . ?
C3 N1 C1 111.7(2) . . ?
C3 N1 Cu1 109.16(17) . . ?
C1 N1 Cu1 139.1(2) . . ?
C4 N2 N3 122.8(2) . . ?
C4 N2 Cu1 119.65(18) . . ?
N3 N2 Cu1 117.57(14) . . ?
C6 N3 N2 106.36(19) . . ?
C8 N4 C9 110.7(3) . . ?
C8 N4 C10 108.8(2) . . ?
C9 N4 C10 108.2(2) . . ?
C8 N4 C7 110.4(2) . . ?
C9 N4 C7 110.8(2) . . ?
C10 N4 C7 107.8(2) . . ?
N6 N5 Cu1 122.15(19) . . ?
N7 N6 N5 176.2(3) . . ?
N1 C1 C2 113.6(3) . . ?
N1 C1 H1 123.2 . . ?
C2 C1 H1 123.2 . . ?
C1 C2 S1 110.9(2) . . ?
C1 C2 H2 124.5 . . ?
S1 C2 H2 124.5 . . ?
N1 C3 C4 120.3(2) . . ?
N1 C3 S1 114.1(2) . . ?
C4 C3 S1 125.6(2) . . ?
N2 C4 C3 110.1(2) . . ?
N2 C4 C5 126.2(2) . . ?
C3 C4 C5 123.7(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 N3 126.6(2) . . ?
O1 C6 C7 118.6(2) . . ?
N3 C6 C7 114.8(2) . . ?
C6 C7 N4 112.4(2) . . ?
C6 C7 H7A 109.1 . . ?
N4 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
N4 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 O2 H2A 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F2B B1 F3B 111.6(15) . . ?
F4A B1 F1A 117.0(8) . . ?
F2B B1 F1B 111.1(12) . . ?
F3B B1 F1B 110.2(13) . . ?
F4A B1 F3A 115.9(8) . . ?
F1A B1 F3A 106.2(7) . . ?
F2B B1 F4B 120.9(12) . . ?
F3B B1 F4B 99.3(18) . . ?
F1B B1 F4B 102.9(10) . . ?
F4A B1 F2A 104.9(7) . . ?
F1A B1 F2A 108.0(6) . . ?
F3A B1 F2A 103.7(7) . . ?
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 N5 1.922(2) . ?
Cu1 N2 1.928(2) . ?
Cu1 O1 1.9694(17) . ?
Cu1 N1 2.048(2) . ?
S1 C2 1.698(4) . ?
S1 C3 1.702(2) . ?
O1 C6 1.276(3) . ?
N1 C3 1.315(4) . ?
N1 C1 1.366(4) . ?
N2 C4 1.298(3) . ?
N2 N3 1.377(3) . ?
N3 C6 1.321(3) . ?
N4 C8 1.496(4) . ?
N4 C9 1.504(4) . ?
N4 C10 1.504(4) . ?
N4 C7 1.512(3) . ?
N5 N6 1.209(3) . ?
N6 N7 1.131(3) . ?
C1 C2 1.366(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.465(4) . ?
C4 C5 1.481(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.503(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O2 C11 1.449(4) . ?
O2 H2A 0.8200 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
B1 F2B 1.241(15) . ?
B1 F3B 1.256(17) . ?
B1 F4A 1.320(14) . ?
B1 F1A 1.351(9) . ?
B1 F1B 1.368(16) . ?
B1 F3A 1.379(10) . ?
B1 F4B 1.389(19) . ?
B1 F2A 1.425(10) . ?
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
C4 N2 N3 C6 -174.4(2) . . . . ?
Cu1 N2 N3 C6 5.3(2) . . . . ?
C3 N1 C1 C2 -0.5(3) . . . . ?
Cu1 N1 C1 C2 -179.6(2) . . . . ?
N1 C1 C2 S1 -0.1(3) . . . . ?
C3 S1 C2 C1 0.5(2) . . . . ?
C1 N1 C3 C4 -177.0(2) . . . . ?
Cu1 N1 C3 C4 2.4(3) . . . . ?
C1 N1 C3 S1 0.8(3) . . . . ?
Cu1 N1 C3 S1 -179.76(11) . . . . ?
C2 S1 C3 N1 -0.8(2) . . . . ?
C2 S1 C3 C4 176.9(2) . . . . ?
N3 N2 C4 C3 -178.7(2) . . . . ?
Cu1 N2 C4 C3 1.6(3) . . . . ?
N3 N2 C4 C5 2.6(4) . . . . ?
Cu1 N2 C4 C5 -177.2(2) . . . . ?
N1 C3 C4 N2 -2.7(3) . . . . ?
S1 C3 C4 N2 179.73(18) . . . . ?
N1 C3 C4 C5 176.1(3) . . . . ?
S1 C3 C4 C5 -1.5(4) . . . . ?
Cu1 O1 C6 N3 -5.6(3) . . . . ?
Cu1 O1 C6 C7 175.65(17) . . . . ?
N2 N3 C6 O1 0.4(3) . . . . ?
N2 N3 C6 C7 179.3(2) . . . . ?
O1 C6 C7 N4 -58.6(3) . . . . ?
N3 C6 C7 N4 122.4(2) . . . . ?
C8 N4 C7 C6 -50.4(3) . . . . ?
C9 N4 C7 C6 72.7(3) . . . . ?
C10 N4 C7 C6 -169.1(2) . . . . ?
