#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:20:36 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266137 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/05/7060576.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_7060576
loop_
_publ_author_name
'Kordestani, Nazanin'
'Amiri Rudbari, Hadi'
'Correia, Isabel'
'Valente, Andreia'
'Côrte-Real, Leonor'
'Islam, Mohammad Khairul'
'Micale, Nicola'
'Braun, Jason D.'
'Herbert, David E.'
'Tumanov, Nikolay'
'Wouters, Johan'
'Enamullah, Mohammed'
_publ_section_title
;
 Heteroleptic enantiopure Pd(ii)-complexes derived from
 halogen-substituted Schiff bases and 2-picolylamine: synthesis,
 experimental and computational characterization and investigation of the
 influence of chirality and halogen atoms on the anticancer activity
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9163
_journal_page_last               9180
_journal_paper_doi               10.1039/D1NJ01491A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C16 H9 F4 N O'
_chemical_formula_sum            'C16 H9 F4 N O'
_chemical_formula_weight         307.24
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc24sc5h
_audit_creation_date             2020-02-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-11 deposited with the CCDC.	2021-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.435(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.2128(8)
_cell_length_b                   5.00270(10)
_cell_length_c                   10.2514(3)
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.72
_cell_measurement_theta_min      3.89
_cell_volume                     1341.90(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Bruker APEXII D8 Venture CMOS diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14917
_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         30.129
_diffrn_reflns_theta_min         2.335
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0543
_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)+(0.0524P)²+0.3476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2801
_reflns_number_total             3929
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj01491a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7060575--7060596.cif.'
_cod_database_code               7060576
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C13(H13), C12(H12), C4(H4), C5(H5), C6(H6)
2.b :
 C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
N1 N 0.26488(5) 0.0391(3) 0.74546(13) 0.0156(3) Uani 1 1 d . . . . .
H1 H 0.2563(7) 0.194(4) 0.7234(18) 0.019 Uiso 1 1 d R . . . .
F1 F 0.06785(4) 0.1380(2) 0.23999(10) 0.0324(3) Uani 1 1 d . . . . .
F2 F 0.02020(4) -0.0659(2) 0.37082(11) 0.0323(3) Uani 1 1 d . . . . .
F3 F 0.03756(4) 0.3489(2) 0.40037(10) 0.0279(3) Uani 1 1 d . . . . .
F4 F 0.15096(4) 0.3861(2) 0.35961(10) 0.0267(3) Uani 1 1 d . . . . .
O1 O 0.24289(5) -0.4004(2) 0.73028(11) 0.0210(3) Uani 1 1 d . . . . .
C16 C 0.47305(8) 0.4719(4) 0.8461(2) 0.0362(5) Uani 1 1 d . . . . .
H16 H 0.501369 0.583086 0.829920 0.043 Uiso 1 1 calc R . . . .
C15 C 0.43783(7) 0.3336(4) 0.86624(18) 0.0260(4) Uani 1 1 d . . . . .
C3 C 0.39509(7) 0.1640(3) 0.89056(17) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.35029(6) 0.1804(3) 0.80995(16) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.347791 0.307114 0.740844 0.021 Uiso 1 1 calc R . . . .
C1 C 0.30954(6) 0.0127(3) 0.83040(15) 0.0152(3) Uani 1 1 d . . . . .
C7 C 0.23502(6) -0.1659(3) 0.70049(15) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.19031(6) -0.0873(3) 0.61085(15) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.19225(7) 0.1247(3) 0.52313(15) 0.0171(3) Uani 1 1 d . . . . .
H9 H 0.222565 0.226940 0.517273 0.020 Uiso 1 1 calc R . . . .
C10 C 0.14898(7) 0.1819(3) 0.44509(15) 0.0176(3) Uani 1 1 d . . . . .
C11 C 0.10378(6) 0.0408(3) 0.45138(15) 0.0172(3) Uani 1 1 d . . . . .
C14 C 0.05735(7) 0.1153(3) 0.36574(16) 0.0198(4) Uani 1 1 d . . . . .
C13 C 0.14554(7) -0.2348(3) 0.61741(16) 0.0180(3) Uani 1 1 d . . . . .
H13 H 0.144661 -0.382141 0.675692 0.022 Uiso 1 1 calc R . . . .
C12 C 0.10232(7) -0.1694(3) 0.54009(16) 0.0193(4) Uani 1 1 d . . . . .
H12 H 0.071642 -0.267845 0.547486 0.023 Uiso 1 1 calc R . . . .
C4 C 0.39810(7) -0.0213(4) 0.99289(17) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.428399 -0.034720 1.048158 0.029 Uiso 1 1 calc R . . . .
C5 C 0.35688(7) -0.1845(4) 1.01326(17) 0.0251(4) Uani 1 1 d . . . . .
H5 H 0.358899 -0.308038 1.083766 0.030 Uiso 1 1 calc R . . . .
C6 C 0.31255(7) -0.1713(3) 0.93256(16) 0.0208(4) Uani 1 1 d . . . . .
H6 H 0.284579 -0.286228 0.946797 0.025 Uiso 1 1 calc R . . . .
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'
O O 0.0106 0.0060 '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'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC05904H 2020
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
C1 N1 H1 116.7(13) . . ?
C7 N1 H1 118.1(13) . . ?
C7 N1 C1 125.17(13) . . ?
C15 C16 H16 180.0 . . ?
C16 C15 C3 179.7(2) . . ?
C2 C3 C15 119.90(16) . . ?
C2 C3 C4 119.35(16) . . ?
C4 C3 C15 120.74(16) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.25(15) . . ?
C1 C2 H2 119.9 . . ?
C2 C1 N1 117.73(14) . . ?
C2 C1 C6 120.33(15) . . ?
C6 C1 N1 121.93(15) . . ?
N1 C7 C8 115.18(13) . . ?
O1 C7 N1 123.67(15) . . ?
O1 C7 C8 121.15(14) . . ?
C9 C8 C7 122.55(15) . . ?
C13 C8 C7 117.55(14) . . ?
C13 C8 C9 119.90(15) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.16(15) . . ?
C10 C9 H9 120.9 . . ?
F4 C10 C9 118.15(15) . . ?
F4 C10 C11 118.87(14) . . ?
C9 C10 C11 122.97(15) . . ?
C10 C11 C14 120.76(15) . . ?
C10 C11 C12 118.20(15) . . ?
C12 C11 C14 121.04(15) . . ?
F1 C14 C11 112.16(14) . . ?
F2 C14 F1 106.72(13) . . ?
F2 C14 F3 106.74(14) . . ?
F2 C14 C11 112.08(14) . . ?
F3 C14 F1 106.70(13) . . ?
F3 C14 C11 112.05(13) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.75(15) . . ?
C12 C13 H13 119.6 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.98(16) . . ?
C13 C12 H12 120.0 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.74(16) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.12(16) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.19(16) . . ?
C5 C6 H6 120.4 . . ?
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
N1 H1 0.836(19) . ?
N1 C1 1.423(2) . ?
N1 C7 1.354(2) . ?
F1 C14 1.339(2) . ?
F2 C14 1.334(2) . ?
F3 C14 1.3352(18) . ?
F4 C10 1.3489(18) . ?
O1 C7 1.2269(18) . ?
C16 H16 0.9500 . ?
C16 C15 1.182(3) . ?
C15 C3 1.439(3) . ?
C3 C2 1.397(2) . ?
C3 C4 1.399(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(2) . ?
C1 C6 1.393(2) . ?
C7 C8 1.498(2) . ?
C8 C9 1.393(2) . ?
C8 C13 1.391(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(2) . ?
C10 C11 1.384(2) . ?
C11 C14 1.504(2) . ?
C11 C12 1.392(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.382(2) . ?
C12 H12 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
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
N1 C1 C6 C5 -179.01(15) . . . . ?
N1 C7 C8 C9 34.6(2) . . . . ?
N1 C7 C8 C13 -145.41(15) . . . . ?
F4 C10 C11 C14 -0.7(2) . . . . ?
F4 C10 C11 C12 180.00(14) . . . . ?
O1 C7 C8 C9 -146.01(16) . . . . ?
O1 C7 C8 C13 34.0(2) . . . . ?
C15 C3 C2 C1 178.15(16) . . . . ?
C15 C3 C4 C5 -179.08(17) . . . . ?
C3 C2 C1 N1 179.82(14) . . . . ?
C3 C2 C1 C6 0.9(2) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C1 N1 C7 O1 1.2(3) . . . . ?
C1 N1 C7 C8 -179.35(14) . . . . ?
C7 N1 C1 C2 142.64(16) . . . . ?
C7 N1 C1 C6 -38.4(2) . . . . ?
C7 C8 C9 C10 -179.76(14) . . . . ?
C7 C8 C13 C12 178.29(14) . . . . ?
C8 C9 C10 F4 -179.61(14) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C8 C13 C12 C11 2.1(2) . . . . ?
C9 C8 C13 C12 -1.7(2) . . . . ?
C9 C10 C11 C14 178.76(15) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C14 F1 50.4(2) . . . . ?
C10 C11 C14 F2 170.48(14) . . . . ?
C10 C11 C14 F3 -69.5(2) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C14 C11 C12 C13 179.75(15) . . . . ?
C13 C8 C9 C10 0.2(2) . . . . ?
C12 C11 C14 F1 -130.33(16) . . . . ?
C12 C11 C14 F2 -10.3(2) . . . . ?
C12 C11 C14 F3 109.68(17) . . . . ?
C4 C3 C2 C1 -0.7(2) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
