#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/46/7234627.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_7234627
loop_
_publ_author_name
'Jan Sanning'
'Linda Stegemann'
'Pascal R. Ewen'
'Christian Schwermann'
'Constantin G. Daniliuc'
'Dongdong Zhang'
'Na Lin'
'Lian Duan'
'Daniel Wegner'
'Nikos L. Doltsinis'
'Cristian A. Strassert'
_publ_section_title
;
 Colour-tunable asymmetric cyclometalated Pt(ii) complexes and
 STM-assisted stability assessment of ancillary ligands for OLEDs
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2560
_journal_page_last               2565
_journal_paper_doi               10.1039/C6TC00093B
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C12 H6 F2 N2'
_chemical_formula_weight         216.19
_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
_cell_angle_alpha                90
_cell_angle_beta                 117.5920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.0158(10)
_cell_length_b                   3.69460(10)
_cell_length_c                   24.1833(8)
_cell_measurement_reflns_used    8111
_cell_measurement_temperature    101.(2)
_cell_measurement_theta_max      25.4190
_cell_measurement_theta_min      2.6076
_cell_volume                     1901.71(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      101.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24584
_diffrn_reflns_theta_full        25.45
_diffrn_reflns_theta_max         25.45
_diffrn_reflns_theta_min         2.49
_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0360
_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)+(0.0392P)²+0.9751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                2852
_reflns_number_total             3522
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-2560.cif
_cod_data_source_block           dan7901
_cod_database_code               7234627
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1A 0.25337(7) 0.8740(5) 0.32403(7) 0.0277(4) Uani d . . . 1 . .
N N2A 0.10648(6) 0.7579(4) 0.20105(6) 0.0132(3) Uani d . . . 1 . .
F F1A -0.04026(4) 0.9508(3) 0.03009(4) 0.0181(2) Uani d . . . 1 . .
F F2A -0.18752(4) 0.7791(3) 0.10354(5) 0.0249(3) Uani d . . . 1 . .
C C1A 0.21422(8) 0.8110(5) 0.27493(8) 0.0189(4) Uani d . . . 1 . .
C C2A 0.16648(8) 0.7241(4) 0.21189(7) 0.0147(3) Uani d . . . 1 . .
C C3A 0.18537(8) 0.6164(4) 0.16821(7) 0.0169(4) Uani d . . . 1 . .
H H3A 0.2286 0.6029 0.1784 0.02 Uiso calc U . R 1 . .
C C4A 0.13861(8) 0.5291(5) 0.10895(7) 0.0171(4) Uani d . . . 1 . .
H H4A 0.1491 0.4493 0.0776 0.021 Uiso calc U . R 1 . .
C C5A 0.07646(8) 0.5605(4) 0.09635(7) 0.0145(3) Uani d . . . 1 . .
H H5A 0.0438 0.502 0.0561 0.017 Uiso calc U . R 1 . .
C C6A 0.06185(7) 0.6784(4) 0.14295(7) 0.0117(3) Uani d . . . 1 . .
C C7A -0.00434(7) 0.7087(4) 0.13196(7) 0.0114(3) Uani d . . . 1 . .
C C8A -0.05309(8) 0.8361(4) 0.07655(7) 0.0125(3) Uani d . . . 1 . .
C C9A -0.11463(7) 0.8631(4) 0.06568(7) 0.0148(3) Uani d . . . 1 . .
H H9A -0.1467 0.9524 0.0273 0.018 Uiso calc U . R 1 . .
C C10A -0.12733(7) 0.7544(4) 0.11322(8) 0.0155(4) Uani d . . . 1 . .
C C11A -0.08185(8) 0.6253(4) 0.16960(7) 0.0148(3) Uani d . . . 1 . .
H H11A -0.0921 0.5527 0.2015 0.018 Uiso calc U . R 1 . .
C C12A -0.02066(7) 0.6047(4) 0.17824(7) 0.0129(3) Uani d . . . 1 . .
H H12A 0.0113 0.5171 0.2169 0.015 Uiso calc U . R 1 . .
N N1B 0.75191(7) 0.5620(5) 0.42112(7) 0.0253(4) Uani d . . . 1 . .
N N2B 0.60604(6) 0.3122(4) 0.40164(6) 0.0123(3) Uani d . . . 1 . .
F F1B 0.45552(4) 0.4389(3) 0.42970(4) 0.0171(2) Uani d . . . 1 . .
F F2B 0.31421(4) 0.1408(3) 0.22374(4) 0.0245(3) Uani d . . . 1 . .
C C1B 0.71280(8) 0.4536(5) 0.43140(7) 0.0171(4) Uani d . . . 1 . .
C C2B 0.66567(7) 0.3188(4) 0.44819(7) 0.0137(3) Uani d . . . 1 . .
C C3B 0.68406(8) 0.2139(4) 0.50917(7) 0.0159(4) Uani d . . . 1 . .
H H3B 0.7268 0.2278 0.5401 0.019 Uiso calc U . R 1 . .
C C4B 0.63783(8) 0.0878(4) 0.52349(7) 0.0162(4) Uani d . . . 1 . .
H H4B 0.6483 0.0094 0.5646 0.019 Uiso calc U . R 1 . .
C C5B 0.57634(7) 0.0781(4) 0.47712(7) 0.0134(3) Uani d . . . 1 . .
H H5B 0.5441 -0.0075 0.4861 0.016 Uiso calc U . R 1 . .
C C6B 0.56176(7) 0.1950(4) 0.41688(7) 0.0114(3) Uani d . . . 1 . .
C C7B 0.49629(7) 0.1868(4) 0.36565(7) 0.0109(3) Uani d . . . 1 . .
C C8B 0.44506(7) 0.3006(4) 0.37346(7) 0.0116(3) Uani d . . . 1 . .
C C9B 0.38387(7) 0.2913(4) 0.32730(7) 0.0142(3) Uani d . . . 1 . .
H H9B 0.3501 0.3714 0.3343 0.017 Uiso calc U . R 1 . .
C C10B 0.37425(7) 0.1586(4) 0.27011(7) 0.0151(4) Uani d . . . 1 . .
C C11B 0.42221(7) 0.0453(4) 0.25792(7) 0.0144(3) Uani d . . . 1 . .
H H11B 0.4139 -0.0405 0.2178 0.017 Uiso calc U . R 1 . .
C C12B 0.48294(7) 0.0608(4) 0.30629(7) 0.0129(3) Uani d . . . 1 . .
H H12B 0.5166 -0.0167 0.2989 0.016 Uiso calc U . R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2A N2A C6A . . 116.47(13)
N1A C1A C2A . . 177.55(18)
N2A C2A C3A . . 125.23(15)
N2A C2A C1A . . 115.85(14)
C3A C2A C1A . . 118.92(15)
C2A C3A C4A . . 117.33(15)
C2A C3A H3A . . 121.3
C4A C3A H3A . . 121.3
C5A C4A C3A . . 118.84(15)
C5A C4A H4A . . 120.6
C3A C4A H4A . . 120.6
C4A C5A C6A . . 119.83(15)
C4A C5A H5A . . 120.1
C6A C5A H5A . . 120.1
N2A C6A C5A . . 122.27(15)
N2A C6A C7A . . 115.95(13)
C5A C6A C7A . . 121.73(14)
C8A C7A C12A . . 116.13(14)
C8A C7A C6A . . 123.37(14)
C12A C7A C6A . . 120.51(14)
F1A C8A C9A . . 116.85(13)
F1A C8A C7A . . 119.24(14)
C9A C8A C7A . . 123.89(14)
C10A C9A C8A . . 116.82(14)
C10A C9A H9A . . 121.6
C8A C9A H9A . . 121.6
F2A C10A C11A . . 119.15(14)
F2A C10A C9A . . 117.78(14)
C11A C10A C9A . . 123.07(15)
C10A C11A C12A . . 117.82(14)
C10A C11A H11A . . 121.1
C12A C11A H11A . . 121.1
C11A C12A C7A . . 122.27(15)
C11A C12A H12A . . 118.9
C7A C12A H12A . . 118.9
C6B N2B C2B . . 116.37(13)
N1B C1B C2B . . 176.74(17)
N2B C2B C3B . . 125.05(15)
N2B C2B C1B . . 115.78(14)
C3B C2B C1B . . 119.16(14)
C2B C3B C4B . . 117.54(15)
C2B C3B H3B . . 121.2
C4B C3B H3B . . 121.2
C5B C4B C3B . . 118.99(15)
C5B C4B H4B . . 120.5
C3B C4B H4B . . 120.5
C4B C5B C6B . . 119.68(15)
C4B C5B H5B . . 120.2
C6B C5B H5B . . 120.2
N2B C6B C5B . . 122.35(14)
N2B C6B C7B . . 116.30(13)
C5B C6B C7B . . 121.34(14)
C8B C7B C12B . . 116.29(14)
C8B C7B C6B . . 122.76(14)
C12B C7B C6B . . 120.95(14)
F1B C8B C9B . . 116.99(14)
F1B C8B C7B . . 118.82(13)
C9B C8B C7B . . 124.17(14)
C8B C9B C10B . . 116.24(15)
C8B C9B H9B . . 121.9
C10B C9B H9B . . 121.9
F2B C10B C11B . . 118.77(14)
F2B C10B C9B . . 117.71(14)
C11B C10B C9B . . 123.52(15)
C10B C11B C12B . . 117.64(14)
C10B C11B H11B . . 121.2
C12B C11B H11B . . 121.2
C11B C12B C7B . . 122.13(15)
C11B C12B H12B . . 118.9
C7B C12B H12B . . 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1A C1A . 1.146(2)
N2A C2A . 1.346(2)
N2A C6A . 1.347(2)
F1A C8A . 1.3630(17)
F2A C10A . 1.3560(18)
C1A C2A . 1.457(2)
C2A C3A . 1.387(2)
C3A C4A . 1.389(2)
C3A H3A . 0.95
C4A C5A . 1.383(2)
C4A H4A . 0.95
C5A C6A . 1.396(2)
C5A H5A . 0.95
C6A C7A . 1.489(2)
C7A C8A . 1.391(2)
C7A C12A . 1.400(2)
C8A C9A . 1.380(2)
C9A C10A . 1.379(2)
C9A H9A . 0.95
C10A C11A . 1.378(2)
C11A C12A . 1.387(2)
C11A H11A . 0.95
C12A H12A . 0.95
N1B C1B . 1.149(2)
N2B C6B . 1.348(2)
N2B C2B . 1.351(2)
F1B C8B . 1.3627(17)
F2B C10B . 1.3576(18)
C1B C2B . 1.456(2)
C2B C3B . 1.385(2)
C3B C4B . 1.388(2)
C3B H3B . 0.95
C4B C5B . 1.380(2)
C4B H4B . 0.95
C5B C6B . 1.400(2)
C5B H5B . 0.95
C6B C7B . 1.485(2)
C7B C8B . 1.393(2)
C7B C12B . 1.398(2)
C8B C9B . 1.374(2)
C9B C10B . 1.382(2)
C9B H9B . 0.95
C10B C11B . 1.379(2)
C11B C12B . 1.385(2)
C11B H11B . 0.95
C12B H12B . 0.95
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9A H9A N1B 4_475 0.95 2.59 3.492(2) 157.7
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
C6A N2A C2A C3A . . . . 0.2(2)
C6A N2A C2A C1A . . . . 180.00(14)
N2A C2A C3A C4A . . . . -1.5(3)
C1A C2A C3A C4A . . . . 178.80(16)
C2A C3A C4A C5A . . . . 1.3(2)
C3A C4A C5A C6A . . . . 0.0(2)
C2A N2A C6A C5A . . . . 1.1(2)
C2A N2A C6A C7A . . . . 178.64(14)
C4A C5A C6A N2A . . . . -1.3(2)
C4A C5A C6A C7A . . . . -178.64(15)
N2A C6A C7A C8A . . . . 142.84(15)
C5A C6A C7A C8A . . . . -39.7(2)
N2A C6A C7A C12A . . . . -37.6(2)
C5A C6A C7A C12A . . . . 139.94(16)
C12A C7A C8A F1A . . . . 178.31(13)
C6A C7A C8A F1A . . . . -2.1(2)
C12A C7A C8A C9A . . . . 0.0(2)
C6A C7A C8A C9A . . . . 179.55(15)
F1A C8A C9A C10A . . . . -178.63(14)
C7A C8A C9A C10A . . . . -0.2(2)
C8A C9A C10A F2A . . . . 179.93(14)
C8A C9A C10A C11A . . . . 0.3(2)
F2A C10A C11A C12A . . . . -179.71(14)
C9A C10A C11A C12A . . . . -0.1(2)
C10A C11A C12A C7A . . . . -0.2(2)
C8A C7A C12A C11A . . . . 0.3(2)
C6A C7A C12A C11A . . . . -179.34(14)
C6B N2B C2B C3B . . . . 0.3(2)
C6B N2B C2B C1B . . . . -178.68(14)
N2B C2B C3B C4B . . . . 0.9(3)
C1B C2B C3B C4B . . . . 179.83(15)
C2B C3B C4B C5B . . . . -1.0(2)
C3B C4B C5B C6B . . . . 0.0(2)
C2B N2B C6B C5B . . . . -1.4(2)
C2B N2B C6B C7B . . . . -179.82(13)
C4B C5B C6B N2B . . . . 1.3(2)
C4B C5B C6B C7B . . . . 179.63(14)
N2B C6B C7B C8B . . . . -137.78(16)
C5B C6B C7B C8B . . . . 43.8(2)
N2B C6B C7B C12B . . . . 42.5(2)
C5B C6B C7B C12B . . . . -135.95(16)
C12B C7B C8B F1B . . . . -177.56(13)
C6B C7B C8B F1B . . . . 2.7(2)
C12B C7B C8B C9B . . . . 0.8(2)
C6B C7B C8B C9B . . . . -178.96(15)
F1B C8B C9B C10B . . . . 178.44(14)
C7B C8B C9B C10B . . . . 0.1(2)
C8B C9B C10B F2B . . . . 179.05(14)
C8B C9B C10B C11B . . . . -1.1(2)
F2B C10B C11B C12B . . . . -179.00(14)
C9B C10B C11B C12B . . . . 1.1(2)
C10B C11B C12B C7B . . . . -0.2(2)
C8B C7B C12B C11B . . . . -0.7(2)
C6B C7B C12B C11B . . . . 179.02(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339026
