#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:11:15 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557795.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_1557795
loop_
_publ_author_name
'Qin, Li-Qin'
'Zou, Bi-Qun'
'Qin, Qi-Pin'
'Wang, Zhen-Feng'
'Yang, Lin'
'Tan, Ming-Xiong'
'Liang, Chun-Jie'
'Liang, Hong'
_publ_section_title
;
 Highly cytotoxic, cyclometalated iridium(iii)-5-fluoro-8-quinolinol
 complexes as cancer cell mitochondriotropic agents
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7832
_journal_page_last               7837
_journal_paper_doi               10.1039/D0NJ00465K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C31 H21 F Ir N3 O'
_chemical_formula_sum            'C31 H21 F Ir N3 O'
_chemical_formula_weight         662.71
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-27 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.268(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4485(7)
_cell_length_b                   9.3218(6)
_cell_length_c                   23.3115(14)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.973
_cell_volume                     2485.9(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38204
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.930
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.409
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1502 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.5406.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.803
_refine_diff_density_min         -1.413
_refine_diff_density_rms         0.281
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0280
_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)+(0.0418P)²+0.1620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0796
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4666
_reflns_number_total             5704
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj00465k2.cif
_cod_data_source_block           aaa
_cod_depositor_comments
;Adding full bibliography for 1557795--1557798.cif.

 Adding full bibliography for 1557795--1557798.cif.
;
_cod_database_code               1557795
_shelxl_version_number           2014-3
_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_max   0.645
_shelx_estimated_absorpt_t_min   0.219
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C29(H29), C30(H30)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Ir1 Ir 0.27128(2) 0.73745(2) 0.08223(2) 0.03453(7) Uani 1 1 d . . . . .
F1 F 0.1192(3) 1.0040(4) -0.17038(11) 0.0908(10) Uani 1 1 d . . . . .
O1 O 0.3765(2) 0.8521(3) 0.02340(10) 0.0385(6) Uani 1 1 d . . . . .
N1 N 0.2450(3) 0.9129(3) 0.13185(12) 0.0358(7) Uani 1 1 d . . . . .
N2 N 0.1438(3) 0.8068(3) 0.01910(13) 0.0332(7) Uani 1 1 d . . . . .
N3 N 0.3053(3) 0.5518(3) 0.03967(14) 0.0454(8) Uani 1 1 d . . . . .
C1 C 0.2964(3) 1.0398(4) 0.12448(17) 0.0419(9) Uani 1 1 d . . . . .
H1 H 0.3444 1.0518 0.0936 0.050 Uiso 1 1 calc R . . . .
C2 C 0.2807(3) 1.1531(5) 0.16082(19) 0.0515(11) Uani 1 1 d . . . . .
H2 H 0.3170 1.2407 0.1546 0.062 Uiso 1 1 calc R . . . .
C3 C 0.2098(4) 1.1342(5) 0.20694(18) 0.0540(11) Uani 1 1 d . . . . .
H3 H 0.1990 1.2089 0.2327 0.065 Uiso 1 1 calc R . . . .
C4 C 0.1560(4) 1.0060(5) 0.21441(17) 0.0499(10) Uani 1 1 d . . . . .
H4 H 0.1080 0.9936 0.2453 0.060 Uiso 1 1 calc R . . . .
C5 C 0.1717(3) 0.8937(4) 0.17666(15) 0.0385(9) Uani 1 1 d . . . . .
C6 C 0.1181(4) 0.7510(4) 0.17777(18) 0.0419(10) Uani 1 1 d . . . . .
C7 C 0.0326(4) 0.7124(5) 0.2152(2) 0.0557(12) Uani 1 1 d . . . . .
H7 H 0.0063 0.7786 0.2416 0.067 Uiso 1 1 calc R . . . .
C8 C -0.0128(4) 0.5774(6) 0.2134(2) 0.0695(14) Uani 1 1 d . . . . .
H8 H -0.0697 0.5518 0.2389 0.083 Uiso 1 1 calc R . . . .
C9 C 0.0243(5) 0.4783(6) 0.1743(2) 0.0750(15) Uani 1 1 d . . . . .
H9 H -0.0079 0.3867 0.1730 0.090 Uiso 1 1 calc R . . . .
C10 C 0.1100(4) 0.5165(5) 0.1368(2) 0.0590(12) Uani 1 1 d . . . . .
H10 H 0.1361 0.4485 0.1110 0.071 Uiso 1 1 calc R . . . .
C11 C 0.1584(3) 0.6538(4) 0.13656(16) 0.0396(9) Uani 1 1 d . . . . .
C12 C 0.4092(3) 0.6672(4) 0.13071(17) 0.0431(10) Uani 1 1 d . . . . .
C13 C 0.4680(4) 0.7367(5) 0.1769(2) 0.0570(14) Uani 1 1 d . . . . .
H13 H 0.4405 0.8246 0.1896 0.068 Uiso 1 1 calc R . . . .
C14 C 0.5664(4) 0.6764(7) 0.2039(2) 0.0725(15) Uani 1 1 d . . . . .
H14 H 0.6052 0.7254 0.2338 0.087 Uiso 1 1 calc R . . . .
C15 C 0.6067(5) 0.5454(8) 0.1870(3) 0.086(2) Uani 1 1 d . . . . .
H15 H 0.6711 0.5045 0.2062 0.103 Uiso 1 1 calc R . . . .
C16 C 0.5522(4) 0.4739(6) 0.1416(2) 0.0733(16) Uani 1 1 d . . . . .
H16 H 0.5805 0.3854 0.1300 0.088 Uiso 1 1 calc R . . . .
C17 C 0.4539(4) 0.5350(5) 0.1128(2) 0.0533(11) Uani 1 1 d . . . . .
C18 C 0.3967(4) 0.4729(4) 0.0625(2) 0.0547(12) Uani 1 1 d . . . . .
C19 C 0.4297(5) 0.3498(5) 0.0343(3) 0.0704(15) Uani 1 1 d . . . . .
H19 H 0.4927 0.2966 0.0490 0.084 Uiso 1 1 calc R . . . .
C20 C 0.3726(6) 0.3049(6) -0.0142(3) 0.0812(19) Uani 1 1 d . . . . .
H20 H 0.3968 0.2221 -0.0326 0.097 Uiso 1 1 calc R . . . .
C21 C 0.2779(5) 0.3819(5) -0.0366(2) 0.0728(16) Uani 1 1 d . . . . .
H21 H 0.2365 0.3514 -0.0695 0.087 Uiso 1 1 calc R . . . .
C22 C 0.2475(4) 0.5055(5) -0.0084(2) 0.0566(12) Uani 1 1 d . . . . .
H22 H 0.1846 0.5591 -0.0230 0.068 Uiso 1 1 calc R . . . .
C23 C 0.0291(4) 0.7858(4) 0.01798(19) 0.0429(9) Uani 1 1 d . . . . .
H23 H -0.0044 0.7458 0.0500 0.051 Uiso 1 1 calc R . . . .
C24 C -0.0434(4) 0.8215(5) -0.02970(19) 0.0515(11) Uani 1 1 d . . . . .
H24 H -0.1235 0.8056 -0.0289 0.062 Uiso 1 1 calc R . . . .
C25 C 0.0032(4) 0.8791(5) -0.07671(19) 0.0521(11) Uani 1 1 d . . . . .
H25 H -0.0443 0.9009 -0.1088 0.062 Uiso 1 1 calc R . . . .
C26 C 0.1254(3) 0.9062(4) -0.07674(16) 0.0422(9) Uani 1 1 d . . . . .
C27 C 0.1926(3) 0.8679(4) -0.02756(15) 0.0336(8) Uani 1 1 d . . . . .
C28 C 0.3165(3) 0.8902(4) -0.02301(15) 0.0343(8) Uani 1 1 d . . . . .
C29 C 0.3675(4) 0.9545(4) -0.07024(17) 0.0444(10) Uani 1 1 d . . . . .
H29 H 0.4475 0.9723 -0.0689 0.053 Uiso 1 1 calc R . . . .
C30 C 0.3006(4) 0.9924(5) -0.11941(17) 0.0556(11) Uani 1 1 d . . . . .
H30 H 0.3364 1.0341 -0.1504 0.067 Uiso 1 1 calc R . . . .
C31 C 0.1831(4) 0.9684(5) -0.12196(17) 0.0531(11) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 '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
N1 Ir1 O1 93.56(11) . . ?
N1 Ir1 N2 92.06(11) . . ?
N1 Ir1 N3 174.17(12) . . ?
N2 Ir1 O1 78.12(10) . . ?
N3 Ir1 O1 89.37(10) . . ?
N3 Ir1 N2 93.47(13) . . ?
C11 Ir1 O1 172.11(12) . . ?
C11 Ir1 N1 80.78(14) . . ?
C11 Ir1 N2 96.50(13) . . ?
C11 Ir1 N3 96.77(14) . . ?
C11 Ir1 C12 91.72(15) . . ?
C12 Ir1 O1 94.18(12) . . ?
C12 Ir1 N1 94.16(15) . . ?
C12 Ir1 N2 170.40(13) . . ?
C12 Ir1 N3 80.59(16) . . ?
C28 O1 Ir1 112.0(2) . . ?
C1 N1 Ir1 124.3(3) . . ?
C1 N1 C5 119.8(3) . . ?
C5 N1 Ir1 115.8(3) . . ?
C23 N2 Ir1 128.2(3) . . ?
C23 N2 C27 118.8(3) . . ?
C27 N2 Ir1 112.7(2) . . ?
C18 N3 Ir1 115.1(3) . . ?
C22 N3 Ir1 125.3(3) . . ?
C22 N3 C18 119.5(4) . . ?
N1 C1 C2 122.3(4) . . ?
C1 C2 C3 118.6(4) . . ?
C4 C3 C2 119.6(4) . . ?
C3 C4 C5 120.9(4) . . ?
N1 C5 C4 118.8(4) . . ?
N1 C5 C6 113.5(3) . . ?
C4 C5 C6 127.6(4) . . ?
C7 C6 C5 123.6(4) . . ?
C7 C6 C11 121.4(4) . . ?
C11 C6 C5 115.0(4) . . ?
C8 C7 C6 120.0(4) . . ?
C7 C8 C9 120.8(4) . . ?
C8 C9 C10 119.4(5) . . ?
C9 C10 C11 121.9(4) . . ?
C6 C11 Ir1 114.6(3) . . ?
C10 C11 Ir1 128.7(3) . . ?
C10 C11 C6 116.5(4) . . ?
C13 C12 Ir1 128.4(3) . . ?
C17 C12 Ir1 113.9(3) . . ?
C17 C12 C13 117.6(4) . . ?
C14 C13 C12 121.1(5) . . ?
C15 C14 C13 120.4(6) . . ?
C14 C15 C16 120.4(5) . . ?
C15 C16 C17 120.0(5) . . ?
C12 C17 C16 120.4(5) . . ?
C12 C17 C18 115.8(4) . . ?
C16 C17 C18 123.7(4) . . ?
N3 C18 C17 114.6(4) . . ?
N3 C18 C19 118.7(5) . . ?
C19 C18 C17 126.6(5) . . ?
C20 C19 C18 121.5(5) . . ?
C19 C20 C21 120.1(5) . . ?
C22 C21 C20 117.5(5) . . ?
N3 C22 C21 122.6(5) . . ?
N2 C23 C24 122.3(4) . . ?
C25 C24 C23 119.9(4) . . ?
C24 C25 C26 119.4(4) . . ?
C27 C26 C25 117.6(4) . . ?
C31 C26 C25 124.8(4) . . ?
C31 C26 C27 117.6(4) . . ?
N2 C27 C26 121.9(3) . . ?
N2 C27 C28 115.8(3) . . ?
C26 C27 C28 122.2(3) . . ?
O1 C28 C27 120.5(3) . . ?
O1 C28 C29 123.0(3) . . ?
C29 C28 C27 116.4(3) . . ?
C30 C29 C28 121.4(4) . . ?
C31 C30 C29 120.1(4) . . ?
F1 C31 C26 118.3(4) . . ?
F1 C31 C30 119.6(4) . . ?
C30 C31 C26 122.2(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
Ir1 O1 2.146(2) . ?
Ir1 N1 2.033(3) . ?
Ir1 N2 2.132(3) . ?
Ir1 N3 2.040(3) . ?
Ir1 C11 2.003(4) . ?
Ir1 C12 2.015(4) . ?
F1 C31 1.362(5) . ?
O1 C28 1.307(4) . ?
N1 C1 1.335(5) . ?
N1 C5 1.378(5) . ?
N2 C23 1.327(5) . ?
N2 C27 1.367(4) . ?
N3 C18 1.368(5) . ?
N3 C22 1.349(5) . ?
C1 C2 1.370(5) . ?
C2 C3 1.384(6) . ?
C3 C4 1.359(6) . ?
C4 C5 1.384(5) . ?
C5 C6 1.465(5) . ?
C6 C7 1.385(6) . ?
C6 C11 1.411(6) . ?
C7 C8 1.362(7) . ?
C8 C9 1.377(7) . ?
C9 C10 1.387(6) . ?
C10 C11 1.395(5) . ?
C12 C13 1.405(6) . ?
C12 C17 1.404(6) . ?
C13 C14 1.387(6) . ?
C14 C15 1.369(8) . ?
C15 C16 1.379(8) . ?
C16 C17 1.408(6) . ?
C17 C18 1.441(6) . ?
C18 C19 1.383(6) . ?
C19 C20 1.350(8) . ?
C20 C21 1.385(8) . ?
C21 C22 1.379(6) . ?
C23 C24 1.401(6) . ?
C24 C25 1.349(6) . ?
C25 C26 1.422(5) . ?
C26 C27 1.401(5) . ?
C26 C31 1.392(5) . ?
C27 C28 1.434(5) . ?
C28 C29 1.401(5) . ?
C29 C30 1.398(5) . ?
C30 C31 1.363(6) . ?
