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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/38/1543897.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.
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data_1543897
loop_
_publ_author_name
'Godman, N. P.'
'Barbee, D. B.'
'Carty, F. B.'
'McMillen, C. D.'
'Corley, C. A.'
'Shurdha, E.'
'Iacono, S. T.'
_publ_section_title
;
 Synthesis, characterization, and electrochemical properties of new highly
 processable, hole-transporting fluorocyclic aryl amine polymers
;
_journal_issue                   37
_journal_name_full               'Polym. Chem.'
_journal_page_first              5799
_journal_paper_doi               10.1039/C6PY00966B
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C34 H18 F14 N2'
_chemical_formula_weight         720.50
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-05-10 deposited with the CCDC.
2016-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.613(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.539(5)
_cell_length_b                   5.738(3)
_cell_length_c                   29.193(15)
_cell_measurement_reflns_used    4657
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7407
_cell_measurement_theta_min      2.7512
_cell_volume                     1579.9(14)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku AFC8S, Mercury CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            12052
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.142
_diffrn_reflns_theta_max         25.142
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB, CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       tabular
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0657
_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)+(0.0314P)²+1.8966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1456
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2089
_reflns_number_total             2817
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6py00966b2.cif
_cod_data_source_block           2
_cod_depositor_comments          'Adding full bibliography for 1543897.cif.'
_cod_original_cell_volume        1580.0(14)
_cod_database_code               1543897
_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   0.916
_shelx_estimated_absorpt_t_max   0.990
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
F1 F 0.1239(2) 0.3660(4) 0.02762(6) 0.0721(6) Uani 1 1 d . . . . .
N1 N 0.3534(2) 0.4215(5) 0.11163(8) 0.0516(6) Uani 1 1 d . . . . .
C6 C 0.3933(3) 0.5852(5) 0.07870(9) 0.0483(7) Uani 1 1 d . . . . .
C9 C 0.4785(3) 0.9141(5) 0.01642(9) 0.0474(7) Uani 1 1 d . . . . .
C8 C 0.3411(3) 0.9096(6) 0.02713(10) 0.0537(7) Uani 1 1 d . . . . .
H8A H 0.2754 1.0178 0.0133 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2995(3) 0.7488(6) 0.05779(10) 0.0551(8) Uani 1 1 d . . . . .
H7A H 0.2070 0.7514 0.0643 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5307(3) 0.5863(6) 0.06897(11) 0.0626(9) Uani 1 1 d . . . . .
H11A H 0.5958 0.4779 0.0830 0.075 Uiso 1 1 calc R U . . .
F2 F -0.1314(2) 0.3460(6) 0.06540(10) 0.1163(10) Uani 1 1 d . . . . .
F6 F 0.1903(3) 0.3658(6) 0.18708(8) 0.1113(10) Uani 1 1 d . . . . .
C12 C 0.4619(3) 0.3567(6) 0.14988(9) 0.0508(7) Uani 1 1 d . . . . .
C10 C 0.5715(3) 0.7475(7) 0.03854(11) 0.0654(9) Uani 1 1 d . . . . .
H10A H 0.6645 0.7452 0.0325 0.079 Uiso 1 1 calc R U . . .
F7 F 0.2272(2) 0.0232(5) 0.16286(9) 0.0991(8) Uani 1 1 d . . . . .
C1 C 0.2193(3) 0.3321(6) 0.10819(10) 0.0519(7) Uani 1 1 d . . . . .
C2 C 0.1159(3) 0.3107(6) 0.07191(11) 0.0594(8) Uani 1 1 d . . . . .
C17 C 0.5316(3) 0.1467(6) 0.14912(12) 0.0631(9) Uani 1 1 d . . . . .
H17A H 0.5063 0.0411 0.1251 0.076 Uiso 1 1 calc R U . . .
C13 C 0.4979(4) 0.5133(7) 0.18544(11) 0.0641(9) Uani 1 1 d . . . . .
H13A H 0.4496 0.6539 0.1856 0.077 Uiso 1 1 calc R U . . .
C5 C 0.1658(4) 0.2317(8) 0.14983(12) 0.0707(10) Uani 1 1 d . . . . .
C16 C 0.6414(4) 0.0957(7) 0.18530(15) 0.0772(11) Uani 1 1 d . . . . .
H16A H 0.6901 -0.0448 0.1853 0.093 Uiso 1 1 calc R U . . .
C14 C 0.6065(4) 0.4602(9) 0.22100(12) 0.0845(12) Uani 1 1 d . . . . .
H14A H 0.6313 0.5657 0.2450 0.101 Uiso 1 1 calc R U . . .
C3 C -0.0181(4) 0.2151(8) 0.08138(15) 0.0771(11) Uani 1 1 d . . . . .
F4A F -0.0465(9) 0.017(2) 0.1529(4) 0.122(3) Uani 0.7 1 d . . P A 1
F4B F -0.009(2) -0.058(5) 0.1376(8) 0.141(8) Uani 0.3 1 d . . P A 2
C15 C 0.6774(4) 0.2528(9) 0.22080(14) 0.0832(13) Uani 1 1 d . . . . .
H15A H 0.7502 0.2178 0.2447 0.100 Uiso 1 1 calc R U . . .
C4 C 0.0063(4) 0.1940(9) 0.13383(17) 0.0903(13) Uani 1 1 d . . . . .
F5 F -0.0647(3) 0.3670(8) 0.15213(12) 0.1501(14) Uani 1 1 d . . . . .
F3 F -0.0481(3) 0.0023(5) 0.06158(11) 0.1188(10) 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'
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
_geom_angle_site_symmetry_3
C1 N1 C6 122.4(2) .
C1 N1 C12 120.8(2) .
C6 N1 C12 116.8(2) .
C7 C6 C11 118.7(3) .
C7 C6 N1 121.5(3) .
C11 C6 N1 119.7(3) .
C8 C9 C10 116.0(3) .
C8 C9 C9 121.4(3) 3_675
C10 C9 C9 122.6(3) 3_675
C7 C8 C9 121.9(3) .
C7 C8 H8A 119.1 .
C9 C8 H8A 119.1 .
C6 C7 C8 120.7(3) .
C6 C7 H7A 119.6 .
C8 C7 H7A 119.6 .
C10 C11 C6 120.3(3) .
C10 C11 H11A 119.9 .
C6 C11 H11A 119.9 .
C13 C12 C17 121.1(3) .
C13 C12 N1 118.8(3) .
C17 C12 N1 120.1(3) .
C11 C10 C9 122.4(3) .
C11 C10 H10A 118.8 .
C9 C10 H10A 118.8 .
C2 C1 N1 131.4(3) .
C2 C1 C5 107.8(3) .
N1 C1 C5 120.8(3) .
C1 C2 F1 126.7(3) .
C1 C2 C3 116.6(3) .
F1 C2 C3 116.7(3) .
C12 C17 C16 118.6(3) .
C12 C17 H17A 120.7 .
C16 C17 H17A 120.7 .
C12 C13 C14 119.7(4) .
C12 C13 H13A 120.2 .
C14 C13 H13A 120.2 .
F6 C5 F7 105.4(3) .
F6 C5 C1 113.7(3) .
F7 C5 C1 112.3(3) .
F6 C5 C4 112.1(3) .
F7 C5 C4 109.0(3) .
C1 C5 C4 104.4(3) .
C15 C16 C17 120.2(4) .
C15 C16 H16A 119.9 .
C17 C16 H16A 119.9 .
C15 C14 C13 120.1(4) .
C15 C14 H14A 119.9 .
C13 C14 H14A 119.9 .
F2 C3 F3 104.3(3) .
F2 C3 C2 114.1(3) .
F3 C3 C2 113.0(3) .
F2 C3 C4 112.9(4) .
F3 C3 C4 110.3(4) .
C2 C3 C4 102.4(3) .
C14 C15 C16 120.3(3) .
C14 C15 H15A 119.9 .
C16 C15 H15A 119.9 .
F4A C4 F5 99.0(5) .
F5 C4 F4B 129.3(9) .
F4A C4 C3 119.0(6) .
F5 C4 C3 109.2(4) .
F4B C4 C3 98.8(10) .
F4A C4 C5 114.2(6) .
F5 C4 C5 107.9(4) .
F4B C4 C5 102.9(10) .
C3 C4 C5 106.9(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.344(4) .
N1 C1 1.368(4) .
N1 C6 1.436(4) .
N1 C12 1.453(4) .
C6 C7 1.376(4) .
C6 C11 1.381(4) .
C9 C8 1.392(4) .
C9 C10 1.395(4) .
C9 C9 1.476(5) 3_675
C8 C7 1.385(4) .
C8 H8A 0.9300 .
C7 H7A 0.9300 .
C11 C10 1.379(4) .
C11 H11A 0.9300 .
F2 C3 1.341(4) .
F6 C5 1.324(4) .
C12 C13 1.377(4) .
C12 C17 1.378(5) .
C10 H10A 0.9300 .
F7 C5 1.361(5) .
C1 C2 1.340(4) .
C1 C5 1.502(4) .
C2 C3 1.456(5) .
C17 C16 1.403(5) .
C17 H17A 0.9300 .
C13 C14 1.386(5) .
C13 H13A 0.9300 .
C5 C4 1.539(5) .
C16 C15 1.378(6) .
C16 H16A 0.9300 .
C14 C15 1.369(6) .
C14 H14A 0.9300 .
C3 F3 1.363(5) .
C3 C4 1.519(6) .
F4A C4 1.298(11) .
F4B C4 1.46(3) .
C15 H15A 0.9300 .
C4 F5 1.355(6) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A F1 0.93 2.54 3.341(4) 144.8 1_565
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
C1 N1 C6 C7 34.1(4) .
C12 N1 C6 C7 -144.8(3) .
C1 N1 C6 C11 -148.6(3) .
C12 N1 C6 C11 32.5(4) .
C10 C9 C8 C7 -0.2(5) .
C9 C9 C8 C7 179.8(3) 3_675
C11 C6 C7 C8 0.8(5) .
N1 C6 C7 C8 178.1(3) .
C9 C8 C7 C6 -0.4(5) .
C7 C6 C11 C10 -0.6(5) .
N1 C6 C11 C10 -177.9(3) .
C1 N1 C12 C13 -103.7(4) .
C6 N1 C12 C13 75.2(4) .
C1 N1 C12 C17 79.3(4) .
C6 N1 C12 C17 -101.8(3) .
C6 C11 C10 C9 -0.1(6) .
C8 C9 C10 C11 0.5(5) .
C9 C9 C10 C11 -179.6(4) 3_675
C6 N1 C1 C2 22.4(5) .
C12 N1 C1 C2 -158.8(3) .
C6 N1 C1 C5 -158.6(3) .
C12 N1 C1 C5 20.3(5) .
N1 C1 C2 F1 3.5(6) .
C5 C1 C2 F1 -175.6(3) .
N1 C1 C2 C3 -177.2(3) .
C5 C1 C2 C3 3.6(4) .
C13 C12 C17 C16 -0.5(5) .
N1 C12 C17 C16 176.4(3) .
C17 C12 C13 C14 0.4(5) .
N1 C12 C13 C14 -176.5(3) .
C2 C1 C5 F6 -133.3(3) .
N1 C1 C5 F6 47.4(5) .
C2 C1 C5 F7 107.1(3) .
N1 C1 C5 F7 -72.1(4) .
C2 C1 C5 C4 -10.8(4) .
N1 C1 C5 C4 169.9(3) .
C12 C17 C16 C15 0.4(5) .
C12 C13 C14 C15 -0.2(6) .
C1 C2 C3 F2 127.8(4) .
F1 C2 C3 F2 -52.9(5) .
C1 C2 C3 F3 -113.3(4) .
F1 C2 C3 F3 66.0(4) .
C1 C2 C3 C4 5.4(5) .
F1 C2 C3 C4 -175.3(3) .
C13 C14 C15 C16 0.0(6) .
C17 C16 C15 C14 -0.2(6) .
F2 C3 C4 F4A 93.9(7) .
F3 C3 C4 F4A -22.3(7) .
C2 C3 C4 F4A -142.9(6) .
F2 C3 C4 F5 -18.5(5) .
F3 C3 C4 F5 -134.8(4) .
C2 C3 C4 F5 104.6(4) .
F2 C3 C4 F4B 118.6(9) .
F3 C3 C4 F4B 2.4(10) .
C2 C3 C4 F4B -118.2(9) .
F2 C3 C4 C5 -134.9(4) .
F3 C3 C4 C5 108.8(4) .
C2 C3 C4 C5 -11.8(5) .
F6 C5 C4 F4A -88.7(7) .
F7 C5 C4 F4A 27.6(7) .
C1 C5 C4 F4A 147.8(6) .
F6 C5 C4 F5 20.2(5) .
F7 C5 C4 F5 136.5(4) .
C1 C5 C4 F5 -103.3(4) .
F6 C5 C4 F4B -118.9(10) .
F7 C5 C4 F4B -2.6(10) .
C1 C5 C4 F4B 117.5(10) .
F6 C5 C4 C3 137.5(4) .
F7 C5 C4 C3 -106.2(4) .
C1 C5 C4 C3 14.0(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132519966
