#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/13/7021344.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_7021344
loop_
_publ_author_name
'Habata, Yoichi'
'Oyama, Yosuke'
'Ikeda, Mari'
'Kuwahara, Shunsuke'
_publ_section_title
;
 Argentivorous molecules with two kinds of aromatic side-arms:
 intramolecular competition between side-arms.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8212
_journal_page_last               8217
_journal_paper_doi               10.1039/c3dt00034f
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C52 H48 F4 N4'
_chemical_formula_weight         804.94
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.321(2)
_cell_angle_beta                 71.759(2)
_cell_angle_gamma                63.608(2)
_cell_formula_units_Z            1
_cell_length_a                   8.8124(8)
_cell_length_b                   9.6778(9)
_cell_length_c                   13.3655(12)
_cell_measurement_temperature    90
_cell_volume                     965.98(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD 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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7261
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0795P)²+0.0785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                3437
_reflns_number_total             4723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt00034f.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7021344
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F2 F 0.83651(16) -0.17189(12) 0.03997(9) 0.0327(3) Uani 1 1 d .
F1 F 0.66859(16) -0.18935(13) 0.40808(9) 0.0329(3) Uani 1 1 d .
N2 N 0.25761(17) 0.59495(15) 0.44835(10) 0.0145(3) Uani 1 1 d .
N1 N 0.68734(18) 0.32526(15) 0.34054(10) 0.0148(3) Uani 1 1 d .
C26 C 0.2575(2) 0.84497(18) 0.27310(13) 0.0153(3) Uani 1 1 d .
C20 C 0.3252(2) 0.82002(19) 0.08161(13) 0.0188(3) Uani 1 1 d .
H20 H 0.3657 0.8516 0.0137 0.023 Uiso 1 1 calc R
C19 C 0.2801(2) 0.69882(19) 0.08957(13) 0.0185(4) Uani 1 1 d .
C14 C 0.2160(2) 0.65071(18) 0.19189(13) 0.0161(3) Uani 1 1 d .
C13 C 0.2062(2) 0.72480(18) 0.28326(13) 0.0151(3) Uani 1 1 d .
C21 C 0.3126(2) 0.89698(18) 0.17091(13) 0.0166(3) Uani 1 1 d .
C15 C 0.1663(2) 0.52789(19) 0.19434(14) 0.0201(4) Uani 1 1 d .
H15 H 0.1233 0.4934 0.2606 0.024 Uiso 1 1 calc R
C5 C 0.8399(2) 0.21135(18) 0.25825(13) 0.0165(3) Uani 1 1 d .
H5A H 0.9501 0.1792 0.2773 0.020 Uiso 1 1 calc R
H5B H 0.8551 0.2591 0.1903 0.020 Uiso 1 1 calc R
C11 C 0.8430(2) 0.00998(19) 0.14541(13) 0.0197(4) Uani 1 1 d .
H11 H 0.8842 0.0544 0.0837 0.024 Uiso 1 1 calc R
C7 C 0.7526(2) 0.00304(19) 0.33425(14) 0.0192(4) Uani 1 1 d .
H7 H 0.7307 0.0432 0.4031 0.023 Uiso 1 1 calc R
C12 C 0.1273(2) 0.68819(18) 0.39366(13) 0.0164(3) Uani 1 1 d .
H12A H 0.0418 0.7870 0.4374 0.020 Uiso 1 1 calc R
H12B H 0.0588 0.6321 0.3893 0.020 Uiso 1 1 calc R
C23 C 0.3366(2) 1.1011(2) 0.25089(14) 0.0211(4) Uani 1 1 d .
H23 H 0.3582 1.1896 0.2447 0.025 Uiso 1 1 calc R
C3 C 0.1578(2) 0.60177(19) 0.56079(12) 0.0163(3) Uani 1 1 d .
H3A H 0.0981 0.5341 0.5683 0.020 Uiso 1 1 calc R
H3B H 0.0636 0.7091 0.5847 0.020 Uiso 1 1 calc R
C6 C 0.8125(2) 0.07114(18) 0.24536(13) 0.0168(3) Uani 1 1 d .
C22 C 0.3484(2) 1.02784(19) 0.16355(14) 0.0199(4) Uani 1 1 d .
H22 H 0.3811 1.0644 0.0963 0.024 Uiso 1 1 calc R
C25 C 0.2541(2) 0.92247(19) 0.36223(13) 0.0182(3) Uani 1 1 d .
H25 H 0.2247 0.8872 0.4303 0.022 Uiso 1 1 calc R
C10 C 0.8123(2) -0.11624(19) 0.13757(14) 0.0223(4) Uani 1 1 d .
C1 C 0.5249(2) 0.39093(18) 0.30885(13) 0.0163(3) Uani 1 1 d .
H1A H 0.5337 0.3151 0.2584 0.020 Uiso 1 1 calc R
H1B H 0.5158 0.4853 0.2724 0.020 Uiso 1 1 calc R
C18 C 0.2934(2) 0.6216(2) -0.00308(14) 0.0227(4) Uani 1 1 d .
H18 H 0.3376 0.6520 -0.0707 0.027 Uiso 1 1 calc R
C2 C 0.3568(2) 0.43172(18) 0.40398(13) 0.0160(3) Uani 1 1 d .
H2A H 0.2747 0.4041 0.3831 0.019 Uiso 1 1 calc R
H2B H 0.3911 0.3662 0.4607 0.019 Uiso 1 1 calc R
C16 C 0.1791(2) 0.4591(2) 0.10409(15) 0.0239(4) Uani 1 1 d .
H16 H 0.1439 0.3787 0.1086 0.029 Uiso 1 1 calc R
C9 C 0.7532(2) -0.18642(19) 0.22357(15) 0.0234(4) Uani 1 1 d .
H9 H 0.7327 -0.2731 0.2163 0.028 Uiso 1 1 calc R
C4 C 0.7249(2) 0.44800(18) 0.36783(13) 0.0159(3) Uani 1 1 d .
H4A H 0.6106 0.5384 0.4039 0.019 Uiso 1 1 calc R
H4B H 0.7852 0.4809 0.3020 0.019 Uiso 1 1 calc R
C17 C 0.2443(2) 0.5062(2) 0.00378(15) 0.0262(4) Uani 1 1 d .
H17 H 0.2535 0.4570 -0.0586 0.031 Uiso 1 1 calc R
C24 C 0.2921(2) 1.04578(19) 0.35135(14) 0.0207(4) Uani 1 1 d .
H24 H 0.2888 1.0951 0.4118 0.025 Uiso 1 1 calc R
C8 C 0.7257(2) -0.1229(2) 0.32098(14) 0.0219(4) 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_1
_geom_angle_site_symmetry_3
C3 N2 C2 108.81(12) . .
C3 N2 C12 107.92(12) . .
C2 N2 C12 111.09(12) . .
C4 N1 C5 111.60(13) . .
C4 N1 C1 110.72(12) . .
C5 N1 C1 111.16(12) . .
C13 C26 C25 122.49(15) . .
C13 C26 C21 120.31(14) . .
C25 C26 C21 117.19(14) . .
C19 C20 C21 121.61(15) . .
C19 C20 H20 119.2 . .
C21 C20 H20 119.2 . .
C20 C19 C18 120.76(16) . .
C20 C19 C14 120.04(15) . .
C18 C19 C14 119.20(16) . .
C13 C14 C15 123.79(15) . .
C13 C14 C19 119.24(15) . .
C15 C14 C19 116.97(15) . .
C26 C13 C14 119.77(15) . .
C26 C13 C12 118.11(14) . .
C14 C13 C12 121.93(14) . .
C20 C21 C22 121.71(15) . .
C20 C21 C26 118.91(15) . .
C22 C21 C26 119.35(15) . .
C16 C15 C14 121.74(16) . .
C16 C15 H15 119.1 . .
C14 C15 H15 119.1 . .
N1 C5 C6 110.86(13) . .
N1 C5 H5A 109.5 . .
C6 C5 H5A 109.5 . .
N1 C5 H5B 109.5 . .
C6 C5 H5B 109.5 . .
H5A C5 H5B 108.1 . .
C10 C11 C6 118.87(16) . .
C10 C11 H11 120.6 . .
C6 C11 H11 120.6 . .
C8 C7 C6 119.07(16) . .
C8 C7 H7 120.5 . .
C6 C7 H7 120.5 . .
N2 C12 C13 115.59(13) . .
N2 C12 H12A 108.4 . .
C13 C12 H12A 108.4 . .
N2 C12 H12B 108.4 . .
C13 C12 H12B 108.4 . .
H12A C12 H12B 107.4 . .
C22 C23 C24 120.12(16) . .
C22 C23 H23 119.9 . .
C24 C23 H23 119.9 . .
N2 C3 C4 113.41(13) . 2_666
N2 C3 H3A 108.9 . .
C4 C3 H3A 108.9 2_666 .
N2 C3 H3B 108.9 . .
C4 C3 H3B 108.9 2_666 .
H3A C3 H3B 107.7 . .
C7 C6 C11 119.17(15) . .
C7 C6 C5 119.94(15) . .
C11 C6 C5 120.88(15) . .
C23 C22 C21 121.11(16) . .
C23 C22 H22 119.4 . .
C21 C22 H22 119.4 . .
C24 C25 C26 121.39(16) . .
C24 C25 H25 119.3 . .
C26 C25 H25 119.3 . .
F2 C10 C9 117.97(16) . .
F2 C10 C11 118.47(16) . .
C9 C10 C11 123.53(16) . .
N1 C1 C2 111.68(13) . .
N1 C1 H1A 109.3 . .
C2 C1 H1A 109.3 . .
N1 C1 H1B 109.3 . .
C2 C1 H1B 109.3 . .
H1A C1 H1B 107.9 . .
C17 C18 C19 121.39(17) . .
C17 C18 H18 119.3 . .
C19 C18 H18 119.3 . .
N2 C2 C1 116.32(13) . .
N2 C2 H2A 108.2 . .
C1 C2 H2A 108.2 . .
N2 C2 H2B 108.2 . .
C1 C2 H2B 108.2 . .
H2A C2 H2B 107.4 . .
C15 C16 C17 120.79(17) . .
C15 C16 H16 119.6 . .
C17 C16 H16 119.6 . .
C10 C9 C8 115.76(16) . .
C10 C9 H9 122.1 . .
C8 C9 H9 122.1 . .
N1 C4 C3 113.02(13) . 2_666
N1 C4 H4A 109.0 . .
C3 C4 H4A 109.0 2_666 .
N1 C4 H4B 109.0 . .
C3 C4 H4B 109.0 2_666 .
H4A C4 H4B 107.8 . .
C18 C17 C16 119.90(16) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C25 C24 C23 120.68(16) . .
C25 C24 H24 119.7 . .
C23 C24 H24 119.7 . .
F1 C8 C7 118.67(16) . .
F1 C8 C9 117.73(16) . .
C7 C8 C9 123.59(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F2 C10 1.360(2) .
F1 C8 1.359(2) .
N2 C3 1.473(2) .
N2 C2 1.476(2) .
N2 C12 1.4788(19) .
N1 C4 1.461(2) .
N1 C5 1.465(2) .
N1 C1 1.473(2) .
C26 C13 1.409(2) .
C26 C25 1.433(2) .
C26 C21 1.438(2) .
C20 C19 1.384(2) .
C20 C21 1.396(2) .
C20 H20 0.9500 .
C19 C18 1.434(2) .
C19 C14 1.440(2) .
C14 C13 1.416(2) .
C14 C15 1.433(2) .
C13 C12 1.515(2) .
C21 C22 1.426(2) .
C15 C16 1.364(2) .
C15 H15 0.9500 .
C5 C6 1.509(2) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C11 C10 1.380(2) .
C11 C6 1.394(2) .
C11 H11 0.9500 .
C7 C8 1.373(2) .
C7 C6 1.393(2) .
C7 H7 0.9500 .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C23 C22 1.357(2) .
C23 C24 1.417(2) .
C23 H23 0.9500 .
C3 C4 1.525(2) 2_666
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C22 H22 0.9500 .
C25 C24 1.364(2) .
C25 H25 0.9500 .
C10 C9 1.376(3) .
C1 C2 1.527(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C18 C17 1.354(3) .
C18 H18 0.9500 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C16 C17 1.417(3) .
C16 H16 0.9500 .
C9 C8 1.380(2) .
C9 H9 0.9500 .
C4 C3 1.525(2) 2_666
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C17 H17 0.9500 .
C24 H24 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102429157
