#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/65/7206557.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_7206557
loop_
_publ_author_name
'Mallet, Charlotte'
'Allain, Magali'
'Leriche, Philippe'
'Frère, Pierre'
_publ_section_title
;
 Competition between π--π or furan--perfluorophenyl stacking
 interactions in conjugated compounds prepared from azomethine
 connections
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              5833
_journal_paper_doi               10.1039/c1ce05575e
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C24 H8 F10 N2 O2'
_chemical_formula_sum            'C24 H8 F10 N2 O2'
_chemical_formula_weight         546.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             2010-04-16T10:06:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.06(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4323(9)
_cell_length_b                   7.278(1)
_cell_length_c                   22.578(4)
_cell_measurement_reflns_used    3857
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3.57
_cell_volume                     1055.5(3)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND 3.2d (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19128
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         29
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
PLATON-ABSGAUSS : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.3269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                1397
_reflns_number_total             2630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05575e.txt
_cod_data_source_block           compound3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7206557
loop_
_symmetry_equiv_pos_as_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_calc_flag
C1 C 0.9061(4) 0.0364(3) 0.50134(10) 0.0489(6) Uani 1 d
C2 C 0.8082(4) 0.0890(3) 0.55441(10) 0.0463(6) Uani 1 d
C3 C 0.6159(4) 0.1525(4) 0.56420(11) 0.0538(7) Uani 1 d
C4 C 0.6049(4) 0.1773(4) 0.62527(11) 0.0521(6) Uani 1 d
C5 C 0.7927(4) 0.1305(3) 0.65054(10) 0.0440(6) Uani 1 d
C6 C 0.8683(4) 0.1385(3) 0.71152(10) 0.0436(6) Uani 1 d
C7 C 1.1030(4) 0.1073(3) 0.79070(9) 0.0432(6) Uani 1 d
C8 C 0.9784(4) 0.0486(3) 0.83539(10) 0.0462(6) Uani 1 d
C9 C 1.0438(4) 0.0531(3) 0.89433(11) 0.0543(7) Uani 1 d
C10 C 1.2366(5) 0.1183(4) 0.91049(11) 0.0580(7) Uani 1 d
C11 C 1.3633(4) 0.1795(3) 0.86840(12) 0.0551(7) Uani 1 d
C12 C 1.2974(4) 0.1734(3) 0.80933(10) 0.0496(6) Uani 1 d
N1 N 1.0514(3) 0.0925(3) 0.72955(8) 0.0463(5) Uani 1 d
O1 O 0.9222(2) 0.0736(2) 0.60768(6) 0.0449(4) Uani 1 d
F1 F 0.7908(2) -0.0244(2) 0.82147(6) 0.0607(4) Uani 1 d
F2 F 0.9191(3) -0.0106(2) 0.93520(6) 0.0815(5) Uani 1 d
F3 F 1.3044(3) 0.1204(2) 0.96775(6) 0.0849(6) Uani 1 d
F4 F 1.5536(2) 0.2464(2) 0.88390(7) 0.0794(5) Uani 1 d
F5 F 1.4251(2) 0.2367(2) 0.76890(7) 0.0709(5) Uani 1 d
H1 H 0.818(4) 0.055(3) 0.4666(11) 0.057(7) Uiso 1 d
H3 H 0.511(4) 0.171(3) 0.5347(12) 0.065(8) Uiso 1 d
H4 H 0.493(4) 0.222(3) 0.6448(11) 0.062(8) Uiso 1 d
H6 H 0.768(4) 0.191(3) 0.7368(10) 0.054(7) Uiso 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 0 '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 0.006 '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
C1 C1 C2 126.0(3) 3_756
C1 C1 H1 121.6(15) 3_756
C2 C1 H1 112.4(15) .
C3 C2 O1 109.5(2) .
C3 C2 C1 132.4(2) .
O1 C2 C1 118.0(2) .
C2 C3 C4 107.5(2) .
C2 C3 H3 124.4(16) .
C4 C3 H3 128.0(16) .
C5 C4 C3 107.0(2) .
C5 C4 H4 126.0(16) .
C3 C4 H4 126.9(16) .
C4 C5 O1 109.9(2) .
C4 C5 C6 130.0(2) .
O1 C5 C6 120.0(2) .
N1 C6 C5 123.8(2) .
N1 C6 H6 123.6(14) .
C5 C6 H6 112.4(14) .
C12 C7 C8 115.7(2) .
C12 C7 N1 119.1(2) .
C8 C7 N1 125.1(2) .
F1 C8 C9 117.5(2) .
F1 C8 C7 119.9(2) .
C9 C8 C7 122.5(2) .
F2 C9 C10 120.5(2) .
F2 C9 C8 119.7(2) .
C10 C9 C8 119.7(2) .
F3 C10 C9 120.5(3) .
F3 C10 C11 119.6(3) .
C9 C10 C11 119.9(2) .
F4 C11 C10 120.5(2) .
F4 C11 C12 119.4(2) .
C10 C11 C12 120.0(2) .
F5 C12 C11 118.7(2) .
F5 C12 C7 119.2(2) .
C11 C12 C7 122.1(2) .
C6 N1 C7 117.42(18) .
C5 O1 C2 106.01(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C1 1.323(5) 3_756
C1 C2 1.435(3) .
C1 H1 0.95(3) .
C2 C3 1.350(4) .
C2 O1 1.379(3) .
C3 C4 1.396(4) .
C3 H3 0.93(3) .
C4 C5 1.352(3) .
C4 H4 0.92(3) .
C5 O1 1.374(3) .
C5 C6 1.437(3) .
C6 N1 1.270(3) .
C6 H6 0.96(2) .
C7 C12 1.384(3) .
C7 C8 1.389(3) .
C7 N1 1.407(3) .
C8 F1 1.340(3) .
C8 C9 1.375(3) .
C9 F2 1.338(3) .
C9 C10 1.359(4) .
C10 F3 1.342(3) .
C10 C11 1.360(4) .
C11 F4 1.346(3) .
C11 C12 1.379(3) .
C12 F5 1.342(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196036
