#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/04/7200489.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_7200489
loop_
_publ_author_name
'Serrano-Becerra, J. M.'
'Hernández-Ortega, S.'
'Morales-Morales, D.'
'Valdés-Martínez, J.'
_publ_section_title
;
 Bottom-up design and construction of a non-centrosymmetric network
 through π--π stacking interactions
;
_journal_coden_ASTM              CRECF4
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              226
_journal_page_last               228
_journal_paper_doi               10.1039/b816630g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C17 H12 F5 N2+, Br-'
_chemical_formula_sum            'C17 H12 Br F5 N2'
_chemical_formula_weight         419.20
_chemical_melting_point_gt       444
_chemical_melting_point_lt       446
_chemical_name_common
'1-(2,3,4,5,6-pentafluorobenzyl)-3-benzylimidazolium bromide'
_chemical_name_systematic
;
1-(2,3,4,5,6-pentafluorobenzyl)-3-benzylimidazolium bromide
;
_space_group_IT_number           1
_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                85.980(4)
_cell_angle_beta                 88.527(4)
_cell_angle_gamma                83.187(4)
_cell_formula_units_Z            1
_cell_length_a                   6.4341(12)
_cell_length_b                   7.3046(14)
_cell_length_c                   8.8257(17)
_cell_measurement_reflns_used    2237
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.70
_cell_measurement_theta_min      2.31
_cell_volume                     410.79(14)
_computing_cell_refinement       'SMART V 5.625'
_computing_data_collection       'SMART V 5.625'
_computing_data_reduction        'SAINT V 6.23C'
_computing_molecular_graphics    'SHELXTL V 6.10'
_computing_publication_material  'SHELXTL V 6.10'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX AXS CCD area detector'
_diffrn_measurement_method       '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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3387
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    2.556
_exptl_absorpt_correction_T_max  0.7161
_exptl_absorpt_correction_T_min  0.5244
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0363
_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)+(0.0383P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                2406
_reflns_number_total             2776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B816630G.txt
_cod_data_source_block           074mmd05
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.
 
 Antanas Vaitkus,
 2019-09-17 
;
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7200489
loop_
_symmetry_equiv_pos_as_xyz
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.88614(4) 0.79616(4) 0.70350(4) 0.07038(19) Uani 1 1 d . . .
F1 F 0.1388(4) 0.5420(4) 0.3812(3) 0.0797(8) Uani 1 1 d . . .
F2 F 0.2301(6) 0.4859(5) 0.0881(3) 0.1026(12) Uani 1 1 d . . .
F3 F 0.6176(7) 0.3436(5) 0.0057(3) 0.1121(13) Uani 1 1 d . . .
F4 F 0.9125(7) 0.2500(4) 0.2174(5) 0.1021(13) Uani 1 1 d . . .
F5 F 0.8223(5) 0.3063(4) 0.5105(4) 0.0872(9) Uani 1 1 d . . .
N1 N 0.3187(7) 0.0639(6) 0.8308(4) 0.0464(10) Uani 1 1 d . . .
C2 C 0.4447(8) 0.1580(7) 0.7493(5) 0.0481(11) Uani 1 1 d . . .
H2 H 0.5825 0.1158 0.7242 0.058 Uiso 1 1 calc R . .
N3 N 0.3485(6) 0.3220(5) 0.7074(4) 0.0474(11) Uani 1 1 d . . .
C4 C 0.1480(7) 0.3310(6) 0.7631(5) 0.0576(12) Uani 1 1 d . . .
H4 H 0.0440 0.4304 0.7499 0.069 Uiso 1 1 calc R . .
C5 C 0.1301(7) 0.1700(6) 0.8399(5) 0.0578(12) Uani 1 1 d . . .
H5 H 0.0106 0.1361 0.8905 0.069 Uiso 1 1 calc R . .
C6 C 0.4352(11) 0.4747(8) 0.6159(6) 0.0602(15) Uani 1 1 d . . .
H6A H 0.5634 0.5003 0.6615 0.072 Uiso 1 1 calc R . .
H6B H 0.3359 0.5855 0.6171 0.072 Uiso 1 1 calc R . .
C7 C 0.4806(7) 0.4282(5) 0.4538(4) 0.0474(10) Uani 1 1 d . . .
C8 C 0.3290(7) 0.4700(6) 0.3423(5) 0.0539(11) Uani 1 1 d . . .
C9 C 0.3733(9) 0.4409(7) 0.1932(5) 0.0612(12) Uani 1 1 d . . .
C10 C 0.5708(11) 0.3696(7) 0.1522(5) 0.0707(15) Uani 1 1 d . . .
C11 C 0.7212(9) 0.3248(6) 0.2576(6) 0.0657(13) Uani 1 1 d . . .
C12 C 0.6720(8) 0.3536(6) 0.4078(5) 0.0558(11) Uani 1 1 d . . .
C13 C 0.3709(7) -0.1242(5) 0.9057(5) 0.0517(10) Uani 1 1 d . . .
H13A H 0.4897 -0.1880 0.8535 0.062 Uiso 1 1 calc R . .
H13B H 0.2529 -0.1943 0.8989 0.062 Uiso 1 1 calc R . .
C14 C 0.4228(7) -0.1136(5) 1.0713(4) 0.0475(10) Uani 1 1 d . . .
C15 C 0.6273(7) -0.1537(6) 1.1193(5) 0.0585(11) Uani 1 1 d . . .
H15 H 0.7339 -0.1843 1.0492 0.070 Uiso 1 1 calc R . .
C16 C 0.6735(8) -0.1484(7) 1.2700(6) 0.0667(14) Uani 1 1 d . . .
H16 H 0.8110 -0.1762 1.3018 0.080 Uiso 1 1 calc R . .
C17 C 0.5171(10) -0.1024(7) 1.3731(6) 0.0709(15) Uani 1 1 d . . .
H17 H 0.5486 -0.0993 1.4751 0.085 Uiso 1 1 calc R . .
C18 C 0.3143(9) -0.0607(7) 1.3271(5) 0.0712(14) Uani 1 1 d . . .
H18 H 0.2081 -0.0277 1.3969 0.085 Uiso 1 1 calc R . .
C19 C 0.2700(8) -0.0684(6) 1.1763(5) 0.0606(12) Uani 1 1 d . . .
H19 H 0.1320 -0.0421 1.1452 0.073 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 '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
C2 N1 C5 107.9(4) . . ?
C2 N1 C13 126.4(4) . . ?
C5 N1 C13 125.7(4) . . ?
N1 C2 N3 109.8(4) . . ?
C2 N3 C4 107.9(4) . . ?
C2 N3 C6 127.9(4) . . ?
C4 N3 C6 124.3(4) . . ?
C5 C4 N3 106.7(4) . . ?
C4 C5 N1 107.6(4) . . ?
N3 C6 C7 111.9(4) . . ?
C12 C7 C8 116.9(4) . . ?
C12 C7 C6 121.8(4) . . ?
C8 C7 C6 121.2(5) . . ?
F1 C8 C9 119.0(4) . . ?
F1 C8 C7 119.4(4) . . ?
C9 C8 C7 121.6(5) . . ?
F2 C9 C10 119.8(5) . . ?
F2 C9 C8 121.0(5) . . ?
C10 C9 C8 119.1(4) . . ?
F3 C10 C11 119.3(6) . . ?
F3 C10 C9 119.8(5) . . ?
C11 C10 C9 120.9(4) . . ?
F4 C11 C10 120.6(5) . . ?
F4 C11 C12 120.4(5) . . ?
C10 C11 C12 118.9(5) . . ?
F5 C12 C7 119.5(4) . . ?
F5 C12 C11 118.0(5) . . ?
C7 C12 C11 122.5(4) . . ?
N1 C13 C14 110.8(3) . . ?
C19 C14 C15 118.5(4) . . ?
C19 C14 C13 121.1(4) . . ?
C15 C14 C13 120.4(4) . . ?
C16 C15 C14 120.3(4) . . ?
C17 C16 C15 119.9(5) . . ?
C16 C17 C18 120.4(5) . . ?
C17 C18 C19 119.1(5) . . ?
C14 C19 C18 121.7(4) . . ?
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
F1 C8 1.320(5) . ?
F2 C9 1.321(5) . ?
F3 C10 1.342(5) . ?
F4 C11 1.336(7) . ?
F5 C12 1.341(5) . ?
N1 C2 1.296(6) . ?
N1 C5 1.364(6) . ?
N1 C13 1.487(5) . ?
C2 N3 1.315(7) . ?
N3 C4 1.365(6) . ?
N3 C6 1.485(7) . ?
C4 C5 1.331(6) . ?
C6 C7 1.507(7) . ?
C7 C12 1.351(6) . ?
C7 C8 1.396(6) . ?
C8 C9 1.365(6) . ?
C9 C10 1.365(7) . ?
C10 C11 1.355(8) . ?
C11 C12 1.380(7) . ?
C13 C14 1.517(5) . ?
C14 C19 1.361(6) . ?
C14 C15 1.384(6) . ?
C15 C16 1.374(6) . ?
C16 C17 1.367(8) . ?
C17 C18 1.370(7) . ?
C18 C19 1.374(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25940796
2 PubChem 129772188
