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#$Date: 2025-07-06 18:40:22 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300789 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/86/7718684.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_7718684
loop_
_publ_author_name
'Monti, Nicola'
'Previati, Eleonora'
'Vigarani, Giulia'
'Cocchi, Massimo'
'Tinti, Francesca'
'Raiteri, Paolo'
'Zacchini, Stefano'
'Giorgini, Loris'
'Massi, Massimiliano'
'Stagni, Stefano'
'Fiorini, Valentina'
_publ_section_title
;
 Fine color-tuning of Ir(III) tetrazolato complexes: synthesis,
 photophysical properties and OLED device fabrication.
;
_journal_issue                   26
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10304
_journal_page_last               10317
_journal_paper_doi               10.1039/d4dt03525a
_journal_volume                  54
_journal_year                    2025
_chemical_formula_sum            'C31 H17 F3 Ir N9'
_chemical_formula_weight         764.73
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-12-17 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.660(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1158(13)
_cell_length_b                   14.7808(16)
_cell_length_c                   20.394(2)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7345
_cell_measurement_theta_min      2.224
_cell_volume                     3516.6(6)
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'PHOTON2 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29645
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.724
_exptl_absorpt_coefficient_mu    3.844
_exptl_absorpt_correction_T_max  0.4315
_exptl_absorpt_correction_T_min  0.2659
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1466 (selected reflections only, before parameter refinement)
 R(int) =  0.0753(selected reflections only, after parameter refinement)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       plate
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         4.172
_refine_diff_density_min         -1.640
_refine_diff_density_rms         0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6116
_refine_ls_number_restraints     300
_refine_ls_restrained_S_all      1.235
_refine_ls_R_factor_all          0.1706
_refine_ls_R_factor_gt           0.1300
_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)+(0.0652P)²+176.2884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2689
_refine_ls_wR_factor_ref         0.2943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4338
_reflns_number_total             6116
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt03525a2.cif
_cod_data_source_block           xp21c_sq
_cod_depositor_comments          'Adding full bibliography for 7718684.cif.'
_cod_original_cell_volume        3516.6(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7718684
_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   0.578
_shelx_estimated_absorpt_t_max   0.656
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
Ir1 Ir 0.28230(7) 0.86480(6) 0.60309(4) 0.0406(3) Uani 1 1 d . . . . .
N1 N 0.3238(12) 0.9402(10) 0.5253(7) 0.026(3) Uani 1 1 d . U . . .
N2 N 0.2992(13) 1.0203(11) 0.4936(8) 0.036(3) Uani 1 1 d . U . . .
N5 N 0.3905(15) 0.7740(11) 0.5643(8) 0.039(3) Uani 1 1 d . U . . .
N3 N 0.3475(14) 1.0235(12) 0.4437(9) 0.040(3) Uani 1 1 d . U . . .
N4 N 0.4064(14) 0.9468(12) 0.4411(9) 0.041(3) Uani 1 1 d . U . . .
N6 N 0.1289(14) 0.8313(12) 0.5392(8) 0.037(3) Uani 1 1 d . U . . .
N7 N 0.4244(15) 0.8992(13) 0.6774(9) 0.044(3) Uani 1 1 d . U . . .
N8 N -0.299(2) 0.747(2) 0.3999(13) 0.087(7) Uani 1 1 d . U . . .
N9 N 0.785(3) 0.980(2) 0.8831(18) 0.136(10) Uani 1 1 d . U . . .
C1 C 0.3883(16) 0.8986(14) 0.4915(10) 0.032(3) Uani 1 1 d . U . . .
C2 C 0.4339(19) 0.8099(15) 0.5137(10) 0.040(3) Uani 1 1 d . U . . .
C3 C 0.515(2) 0.7658(16) 0.4898(12) 0.051(4) Uani 1 1 d . U . . .
H3 H 0.5452 0.7932 0.4561 0.062 Uiso 1 1 calc R U . . .
C4 C 0.553(2) 0.6824(18) 0.5150(13) 0.063(4) Uani 1 1 d . U . . .
H4 H 0.6067 0.6503 0.4974 0.075 Uiso 1 1 calc R U . . .
C5 C 0.514(3) 0.6454(19) 0.5654(14) 0.071(4) Uani 1 1 d . U . . .
C6 C 0.429(2) 0.6933(16) 0.5877(13) 0.056(4) Uani 1 1 d . U . . .
H6 H 0.3987 0.6661 0.6213 0.067 Uiso 1 1 calc R U . . .
C7 C 0.554(4) 0.559(2) 0.599(2) 0.097(5) Uani 1 1 d . U . . .
C8 C 0.1816(16) 0.9585(14) 0.6317(10) 0.031(3) Uani 1 1 d . U . . .
C9 C 0.2147(17) 1.0277(15) 0.6788(10) 0.038(4) Uani 1 1 d . U . . .
H9 H 0.2927 1.0313 0.7043 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1408(16) 1.0899(15) 0.6898(10) 0.034(3) Uani 1 1 d . U . . .
H10 H 0.1662 1.1407 0.7184 0.041 Uiso 1 1 calc R U . . .
C11 C 0.0214(18) 1.0759(16) 0.6559(11) 0.043(4) Uani 1 1 d . U . . .
H11 H -0.0346 1.1129 0.6676 0.051 Uiso 1 1 calc R U . . .
C12 C -0.0129(18) 1.0105(15) 0.6073(11) 0.041(4) Uani 1 1 d . U . . .
H12 H -0.0910 1.0061 0.5821 0.049 Uiso 1 1 calc R U . . .
C13 C 0.0650(17) 0.9526(14) 0.5956(10) 0.035(3) Uani 1 1 d . U . . .
C14 C 0.0375(17) 0.8793(14) 0.5462(10) 0.036(3) Uani 1 1 d . U . . .
C15 C -0.0722(18) 0.8586(16) 0.5061(10) 0.042(4) Uani 1 1 d . U . . .
H15 H -0.1360 0.8940 0.5093 0.050 Uiso 1 1 calc R U . . .
C16 C -0.0875(19) 0.7864(17) 0.4619(11) 0.047(4) Uani 1 1 d . U . . .
C17 C 0.0029(19) 0.7372(17) 0.4568(11) 0.048(4) Uani 1 1 d . U . . .
H17 H -0.0077 0.6860 0.4276 0.057 Uiso 1 1 calc R U . . .
C18 C 0.1128(19) 0.7620(16) 0.4949(11) 0.042(4) Uani 1 1 d . U . . .
H18 H 0.1772 0.7294 0.4894 0.051 Uiso 1 1 calc R U . . .
C19 C -0.204(2) 0.7641(19) 0.4254(13) 0.058(5) Uani 1 1 d . U . . .
C20 C 0.2579(17) 0.7844(14) 0.6792(10) 0.035(3) Uani 1 1 d . U . . .
C21 C 0.1753(19) 0.7265(15) 0.6748(12) 0.045(4) Uani 1 1 d . U . . .
H21 H 0.1164 0.7216 0.6334 0.053 Uiso 1 1 calc R U . . .
C22 C 0.171(2) 0.6689(18) 0.7326(13) 0.059(4) Uani 1 1 d . U . . .
H22 H 0.1136 0.6242 0.7288 0.071 Uiso 1 1 calc R U . . .
C23 C 0.255(2) 0.6820(19) 0.7927(13) 0.059(4) Uani 1 1 d . U . . .
H23 H 0.2518 0.6503 0.8326 0.070 Uiso 1 1 calc R U . . .
C24 C 0.341(2) 0.7397(17) 0.7946(12) 0.055(4) Uani 1 1 d . U . . .
H24 H 0.3994 0.7458 0.8362 0.066 Uiso 1 1 calc R U . . .
C25 C 0.3494(19) 0.7905(16) 0.7401(11) 0.044(3) Uani 1 1 d . U . . .
C26 C 0.4370(19) 0.8559(16) 0.7383(11) 0.046(3) Uani 1 1 d . U . . .
C27 C 0.532(2) 0.8729(18) 0.7933(13) 0.061(4) Uani 1 1 d . U . . .
H27 H 0.5429 0.8416 0.8353 0.073 Uiso 1 1 calc R U . . .
C28 C 0.609(2) 0.935(2) 0.7848(15) 0.074(5) Uani 1 1 d . U . . .
C29 C 0.592(2) 0.982(2) 0.7246(13) 0.065(5) Uani 1 1 d . U . . .
H29 H 0.6436 1.0285 0.7196 0.078 Uiso 1 1 calc R U . . .
C30 C 0.4971(19) 0.9602(17) 0.6715(12) 0.051(4) Uani 1 1 d . U . . .
H30 H 0.4854 0.9910 0.6293 0.061 Uiso 1 1 calc R U . . .
C31 C 0.704(3) 0.961(2) 0.8409(17) 0.095(6) Uani 1 1 d . U . . .
F1 F 0.459(2) 0.4947(15) 0.5780(12) 0.133(6) Uani 1 1 d . U . . .
F2 F 0.5795(18) 0.5582(12) 0.6631(10) 0.107(6) Uani 1 1 d . U . . .
F3 F 0.611(2) 0.5130(15) 0.5727(12) 0.139(7) Uani 1 1 d . 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'
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'
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
N6 Ir1 N7 172.0(7) . . ?
N6 Ir1 C8 80.4(7) . . ?
N7 Ir1 C8 94.0(8) . . ?
N6 Ir1 C20 92.9(7) . . ?
N7 Ir1 C20 81.1(8) . . ?
C8 Ir1 C20 87.5(8) . . ?
N6 Ir1 N1 90.5(6) . . ?
N7 Ir1 N1 95.9(7) . . ?
C8 Ir1 N1 98.0(7) . . ?
C20 Ir1 N1 173.9(7) . . ?
N6 Ir1 N5 98.9(7) . . ?
N7 Ir1 N5 87.3(7) . . ?
C8 Ir1 N5 174.2(7) . . ?
C20 Ir1 N5 98.2(7) . . ?
N1 Ir1 N5 76.2(6) . . ?
C1 N1 N2 104.1(15) . . ?
C1 N1 Ir1 116.1(13) . . ?
N2 N1 Ir1 139.6(12) . . ?
N3 N2 N1 108.6(16) . . ?
C6 N5 C2 116.5(19) . . ?
C6 N5 Ir1 128.0(16) . . ?
C2 N5 Ir1 115.1(13) . . ?
N2 N3 N4 110.8(17) . . ?
C1 N4 N3 102.9(17) . . ?
C18 N6 C14 119.6(18) . . ?
C18 N6 Ir1 124.1(14) . . ?
C14 N6 Ir1 116.1(14) . . ?
C30 N7 C26 120(2) . . ?
C30 N7 Ir1 124.7(15) . . ?
C26 N7 Ir1 115.2(15) . . ?
N4 C1 N1 113.6(18) . . ?
N4 C1 C2 127.2(19) . . ?
N1 C1 C2 119.1(17) . . ?
C3 C2 N5 122(2) . . ?
C3 C2 C1 125(2) . . ?
N5 C2 C1 113.0(18) . . ?
C4 C3 C2 119(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 118(2) . . ?
C4 C5 C7 124(3) . . ?
C6 C5 C7 118(3) . . ?
N5 C6 C5 123(2) . . ?
N5 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
F3 C7 F2 117(3) . . ?
F3 C7 F1 91(3) . . ?
F2 C7 F1 104(3) . . ?
F3 C7 C5 117(3) . . ?
F2 C7 C5 116(3) . . ?
F1 C7 C5 107(3) . . ?
C9 C8 C13 118.0(18) . . ?
C9 C8 Ir1 128.1(15) . . ?
C13 C8 Ir1 113.8(14) . . ?
C10 C9 C8 123(2) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C11 117(2) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
C12 C11 C10 121.3(19) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 122(2) . . ?
C12 C13 C14 123.8(19) . . ?
C8 C13 C14 114.7(17) . . ?
N6 C14 C15 120(2) . . ?
N6 C14 C13 114.9(17) . . ?
C15 C14 C13 125.0(19) . . ?
C16 C15 C14 120(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120(2) . . ?
C17 C16 C19 123(2) . . ?
C15 C16 C19 117(2) . . ?
C16 C17 C18 119(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
N6 C18 C17 121(2) . . ?
N6 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
N8 C19 C16 176(3) . . ?
C21 C20 C25 120(2) . . ?
C21 C20 Ir1 126.7(16) . . ?
C25 C20 Ir1 112.8(15) . . ?
C20 C21 C22 121(2) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 117(2) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C24 C23 C22 120(2) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 124(2) . . ?
C23 C24 H24 118.2 . . ?
C25 C24 H24 118.2 . . ?
C24 C25 C20 117(2) . . ?
C24 C25 C26 127(2) . . ?
C20 C25 C26 115.1(19) . . ?
N7 C26 C27 121(2) . . ?
N7 C26 C25 115.7(19) . . ?
C27 C26 C25 124(2) . . ?
C28 C27 C26 118(2) . . ?
C28 C27 H27 121.1 . . ?
C26 C27 H27 121.1 . . ?
C27 C28 C29 121(2) . . ?
C27 C28 C31 121(3) . . ?
C29 C28 C31 118(3) . . ?
C28 C29 C30 118(3) . . ?
C28 C29 H29 121.1 . . ?
C30 C29 H29 121.1 . . ?
N7 C30 C29 122(2) . . ?
N7 C30 H30 118.8 . . ?
C29 C30 H30 118.8 . . ?
N9 C31 C28 175(5) . . ?
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 N6 2.022(17) . ?
Ir1 N7 2.028(18) . ?
Ir1 C8 2.032(18) . ?
Ir1 C20 2.04(2) . ?
Ir1 N1 2.108(14) . ?
Ir1 N5 2.169(16) . ?
N1 C1 1.33(2) . ?
N1 N2 1.34(2) . ?
N2 N3 1.30(2) . ?
N5 C6 1.32(3) . ?
N5 C2 1.38(3) . ?
N3 N4 1.35(2) . ?
N4 C1 1.32(3) . ?
N6 C18 1.34(3) . ?
N6 C14 1.35(3) . ?
N7 C30 1.29(3) . ?
N7 C26 1.37(3) . ?
N8 C19 1.15(3) . ?
N9 C31 1.16(4) . ?
C1 C2 1.45(3) . ?
C2 C3 1.38(3) . ?
C3 C4 1.37(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.36(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.42(4) . ?
C5 C7 1.47(4) . ?
C6 H6 0.9500 . ?
C7 F3 1.19(4) . ?
C7 F2 1.27(4) . ?
C7 F1 1.47(5) . ?
C8 C9 1.39(3) . ?
C8 C13 1.41(3) . ?
C9 C10 1.34(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.44(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.37(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.34(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.46(3) . ?
C14 C15 1.39(3) . ?
C15 C16 1.38(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.34(3) . ?
C16 C19 1.45(3) . ?
C17 C18 1.40(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C20 C21 1.30(3) . ?
C20 C25 1.43(3) . ?
C21 C22 1.47(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.38(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.34(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.37(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.44(3) . ?
C26 C27 1.40(3) . ?
C27 C28 1.35(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.38(4) . ?
C28 C31 1.44(4) . ?
C29 C30 1.39(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
