#------------------------------------------------------------------------------
#$Date: 2022-07-23 02:31:33 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276815 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/51/7245166.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_7245166
loop_
_publ_author_name
'Topaloğlu Aksoy, Burcu'
'Dedeoglu, Burcu'
'Zorlu, Yunus'
'Ayhan, Mehmet Menaf'
'Çoşut, Bünyemin'
_publ_section_title
;
 Exploring halogen⋯halogen interactions in supramolecular
 self-assemblies of BODIPY networks
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00776B
_journal_year                    2022
_chemical_formula_moiety         'C19 H18 B F2 I N2'
_chemical_formula_sum            'C19 H18 B F2 I N2'
_chemical_formula_weight         450.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-10 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                106.646(8)
_cell_angle_beta                 96.659(8)
_cell_angle_gamma                97.135(8)
_cell_formula_units_Z            2
_cell_length_a                   6.649(2)
_cell_length_b                   10.479(4)
_cell_length_c                   14.000(5)
_cell_measurement_reflns_used    2124
_cell_measurement_temperature    298
_cell_measurement_theta_max      19.61
_cell_measurement_theta_min      2.92
_cell_volume                     915.5(6)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9330
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.036
_diffrn_reflns_theta_max         25.036
_diffrn_reflns_theta_min         1.538
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    1.771
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.7571.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.052
_refine_diff_density_max         1.029
_refine_diff_density_min         -1.081
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         9330
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0729
_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)+(0.1115P)²+1.5317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6236
_reflns_number_total             9330
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00776b2.cif
_cod_data_source_block           21gtu80_bc_bt_37_0m
_cod_original_cell_volume        915.4(6)
_cod_database_code               7245166
_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_max   0.914
_shelx_estimated_absorpt_t_min   0.814
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.842(4)
 0.158(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid body (RIGU) restrains
 I1, C1, C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
I1 I -0.10350(13) 0.06610(10) 0.69738(8) 0.0529(4) Uani 1 1 d . U . . .
F1 F 0.7452(11) 0.3745(9) 0.8909(6) 0.066(2) Uani 1 1 d . . . . .
F2 F 0.6007(11) 0.5440(8) 0.8626(6) 0.064(2) Uani 1 1 d . . . . .
N1 N 0.4717(14) 0.3218(10) 0.7508(7) 0.037(2) Uani 1 1 d . . . . .
N2 N 0.8171(14) 0.4424(9) 0.7474(7) 0.034(2) Uani 1 1 d . . . . .
C1 C 0.3060(17) 0.2657(12) 0.7819(9) 0.038(3) Uani 1 1 d . U . . .
C2 C 0.1765(16) 0.1858(11) 0.6962(9) 0.033(2) Uani 1 1 d . U . . .
C3 C 0.2538(17) 0.1871(12) 0.6111(10) 0.038(3) Uani 1 1 d . U . . .
H3 H 0.1952 0.1386 0.5450 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4411(16) 0.2769(11) 0.6435(8) 0.030(3) Uani 1 1 d . . . . .
C5 C 0.5935(16) 0.3125(12) 0.5918(8) 0.033(3) Uani 1 1 d . . . . .
C6 C 0.7790(17) 0.3905(12) 0.6419(9) 0.035(3) Uani 1 1 d . . . . .
C7 C 0.9526(18) 0.4365(13) 0.6050(10) 0.044(3) Uani 1 1 d . . . . .
H7 H 0.9694 0.4168 0.5375 0.053 Uiso 1 1 calc R U . . .
C8 C 1.0933(17) 0.5161(13) 0.6867(10) 0.045(3) Uani 1 1 d . . . . .
H8 H 1.2220 0.5607 0.6848 0.053 Uiso 1 1 calc R U . . .
C9 C 1.0056(17) 0.5175(13) 0.7746(9) 0.040(3) Uani 1 1 d . . . . .
C10 C 0.5520(17) 0.2686(12) 0.4805(9) 0.036(3) Uani 1 1 d . U . . .
C11 C 0.657(2) 0.1762(15) 0.4233(10) 0.057(4) Uani 1 1 d . U . . .
H11 H 0.7558 0.1402 0.4551 0.069 Uiso 1 1 calc R U . . .
C12 C 0.614(2) 0.1366(15) 0.3171(11) 0.061(4) Uani 1 1 d . U . . .
H12 H 0.6828 0.0736 0.2788 0.073 Uiso 1 1 calc R U . . .
C13 C 0.473(2) 0.1899(15) 0.2717(11) 0.055(4) Uani 1 1 d . U . . .
H13 H 0.4498 0.1665 0.2016 0.066 Uiso 1 1 calc R U . . .
C14 C 0.365(2) 0.2769(14) 0.3257(10) 0.051(3) Uani 1 1 d . U . . .
H14 H 0.2654 0.3110 0.2928 0.062 Uiso 1 1 calc R U . . .
C15 C 0.4027(19) 0.3157(13) 0.4303(9) 0.045(3) Uani 1 1 d . U . . .
H15 H 0.3255 0.3745 0.4669 0.054 Uiso 1 1 calc R U . . .
C16 C 1.0930(19) 0.5987(14) 0.8792(10) 0.052(4) Uani 1 1 d . . . . .
H16A H 1.2364 0.5900 0.8920 0.062 Uiso 1 1 calc R U . . .
H16B H 1.0220 0.5633 0.9252 0.062 Uiso 1 1 calc R U . . .
C17 C 1.077(3) 0.7485(14) 0.9009(11) 0.072(5) Uani 1 1 d . . . . .
H17A H 1.1284 0.7810 0.8494 0.107 Uiso 1 1 calc R U . . .
H17B H 1.1563 0.7989 0.9654 0.107 Uiso 1 1 calc R U . . .
H17C H 0.9358 0.7597 0.9014 0.107 Uiso 1 1 calc R U . . .
C18 C 0.288(2) 0.2851(15) 0.8910(10) 0.053(4) Uani 1 1 d . . . . .
H18A H 0.3677 0.3715 0.9316 0.064 Uiso 1 1 calc R U . . .
H18B H 0.1454 0.2878 0.8993 0.064 Uiso 1 1 calc R U . . .
C19 C 0.358(2) 0.1777(16) 0.9286(11) 0.069(4) Uani 1 1 d . . . . .
H19A H 0.2562 0.0977 0.9039 0.104 Uiso 1 1 calc R U . . .
H19B H 0.3799 0.2073 1.0011 0.104 Uiso 1 1 calc R U . . .
H19C H 0.4847 0.1584 0.9054 0.104 Uiso 1 1 calc R U . . .
B1 B 0.660(2) 0.4229(16) 0.8172(12) 0.044(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'
B B 0.0013 0.0007 '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'
I I -0.4742 1.8119 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -2.00 -3.00 0.0210
0.00 2.00 3.00 0.0070
-3.00 1.00 2.00 0.0590
2.00 3.00 2.00 0.0250
3.00 -2.00 -3.00 0.0530
0.00 -3.00 -2.00 0.0230
0.00 -3.00 -1.00 0.0260
0.00 -2.00 1.00 0.0320
0.00 2.00 -1.00 0.0100
0.00 2.00 -3.00 0.0100
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
C1 N1 C4 108.4(10) . . ?
C1 N1 B1 127.6(11) . . ?
C4 N1 B1 124.0(10) . . ?
C6 N2 B1 124.7(10) . . ?
C9 N2 C6 107.9(10) . . ?
C9 N2 B1 127.3(10) . . ?
N1 C1 C2 106.6(10) . . ?
N1 C1 C18 123.7(11) . . ?
C2 C1 C18 129.6(11) . . ?
C1 C2 I1 123.9(9) . . ?
C3 C2 I1 123.9(9) . . ?
C3 C2 C1 112.2(11) . . ?
C2 C3 H3 127.2 . . ?
C2 C3 C4 105.7(11) . . ?
C4 C3 H3 127.2 . . ?
C3 C4 N1 107.1(10) . . ?
C5 C4 N1 120.4(10) . . ?
C5 C4 C3 132.1(11) . . ?
C4 C5 C10 118.6(10) . . ?
C6 C5 C4 121.6(10) . . ?
C6 C5 C10 119.7(10) . . ?
N2 C6 C7 108.0(10) . . ?
C5 C6 N2 121.1(10) . . ?
C5 C6 C7 130.9(11) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 C6 107.5(11) . . ?
C8 C7 H7 126.2 . . ?
C7 C8 H8 126.4 . . ?
C7 C8 C9 107.3(11) . . ?
C9 C8 H8 126.4 . . ?
N2 C9 C8 109.3(10) . . ?
N2 C9 C16 123.9(11) . . ?
C8 C9 C16 126.5(11) . . ?
C11 C10 C5 121.6(11) . . ?
C15 C10 C5 120.5(11) . . ?
C15 C10 C11 117.8(12) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(13) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(13) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(14) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(13) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.9(12) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C9 C16 H16A 109.0 . . ?
C9 C16 H16B 109.0 . . ?
C9 C16 C17 113.0(11) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C18 H18A 108.9 . . ?
C1 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C1 113.3(11) . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F1 B1 F2 108.6(12) . . ?
F1 B1 N1 110.6(12) . . ?
F1 B1 N2 110.4(10) . . ?
F2 B1 N1 109.6(10) . . ?
F2 B1 N2 110.2(12) . . ?
N2 B1 N1 107.5(11) . . ?
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
I1 C2 2.116(12) . ?
F1 B1 1.370(18) . ?
F2 B1 1.376(16) . ?
N1 C1 1.359(15) . ?
N1 C4 1.420(14) . ?
N1 B1 1.547(17) . ?
N2 C6 1.400(14) . ?
N2 C9 1.344(14) . ?
N2 B1 1.543(17) . ?
C1 C2 1.374(16) . ?
C1 C18 1.503(17) . ?
C2 C3 1.353(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(16) . ?
C4 C5 1.386(15) . ?
C5 C6 1.379(16) . ?
C5 C10 1.474(16) . ?
C6 C7 1.406(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.419(17) . ?
C9 C16 1.474(17) . ?
C10 C11 1.383(17) . ?
C10 C15 1.373(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.408(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.335(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.347(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(17) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.531(19) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.48(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C2 C3 C4 -178.9(7) . . . . ?
N1 C1 C2 I1 177.5(7) . . . . ?
N1 C1 C2 C3 0.8(14) . . . . ?
N1 C1 C18 C19 -93.3(16) . . . . ?
N1 C4 C5 C6 0.8(17) . . . . ?
N1 C4 C5 C10 -177.4(10) . . . . ?
N2 C6 C7 C8 -0.5(14) . . . . ?
N2 C9 C16 C17 -99.3(15) . . . . ?
C1 N1 C4 C3 -2.3(13) . . . . ?
C1 N1 C4 C5 -176.0(10) . . . . ?
C1 N1 B1 F1 52.6(16) . . . . ?
C1 N1 B1 F2 -67.1(17) . . . . ?
C1 N1 B1 N2 173.2(11) . . . . ?
C1 C2 C3 C4 -2.2(13) . . . . ?
C2 C1 C18 C19 81.9(17) . . . . ?
C2 C3 C4 N1 2.7(13) . . . . ?
C2 C3 C4 C5 175.4(12) . . . . ?
C3 C4 C5 C6 -171.1(12) . . . . ?
C3 C4 C5 C10 10.7(19) . . . . ?
C4 N1 C1 C2 0.9(13) . . . . ?
C4 N1 C1 C18 177.1(11) . . . . ?
C4 N1 B1 F1 -130.4(12) . . . . ?
C4 N1 B1 F2 109.9(13) . . . . ?
C4 N1 B1 N2 -9.9(16) . . . . ?
C4 C5 C6 N2 -3.1(18) . . . . ?
C4 C5 C6 C7 179.3(12) . . . . ?
C4 C5 C10 C11 -113.4(14) . . . . ?
C4 C5 C10 C15 64.7(16) . . . . ?
C5 C6 C7 C8 177.3(13) . . . . ?
C5 C10 C11 C12 -179.9(13) . . . . ?
C5 C10 C15 C14 178.8(12) . . . . ?
C6 N2 C9 C8 0.3(14) . . . . ?
C6 N2 C9 C16 174.3(11) . . . . ?
C6 N2 B1 F1 128.3(12) . . . . ?
C6 N2 B1 F2 -111.8(12) . . . . ?
C6 N2 B1 N1 7.6(16) . . . . ?
C6 C5 C10 C11 68.4(17) . . . . ?
C6 C5 C10 C15 -113.6(13) . . . . ?
C6 C7 C8 C9 0.6(14) . . . . ?
C7 C8 C9 N2 -0.6(14) . . . . ?
C7 C8 C9 C16 -174.4(12) . . . . ?
C8 C9 C16 C17 73.7(17) . . . . ?
C9 N2 C6 C5 -177.9(11) . . . . ?
C9 N2 C6 C7 0.1(13) . . . . ?
C9 N2 B1 F1 -56.4(17) . . . . ?
C9 N2 B1 F2 63.6(17) . . . . ?
C9 N2 B1 N1 -177.1(11) . . . . ?
C10 C5 C6 N2 175.1(10) . . . . ?
C10 C5 C6 C7 -2(2) . . . . ?
C10 C11 C12 C13 1(2) . . . . ?
C11 C10 C15 C14 -3.1(19) . . . . ?
C11 C12 C13 C14 -3(2) . . . . ?
C12 C13 C14 C15 2(2) . . . . ?
C13 C14 C15 C10 1(2) . . . . ?
C15 C10 C11 C12 2(2) . . . . ?
C18 C1 C2 I1 1.6(18) . . . . ?
C18 C1 C2 C3 -175.1(12) . . . . ?
B1 N1 C1 C2 178.3(11) . . . . ?
B1 N1 C1 C18 -5.5(19) . . . . ?
B1 N1 C4 C3 -179.7(11) . . . . ?
B1 N1 C4 C5 6.5(17) . . . . ?
B1 N2 C6 C5 -1.8(18) . . . . ?
B1 N2 C6 C7 176.3(11) . . . . ?
B1 N2 C9 C8 -175.7(11) . . . . ?
B1 N2 C9 C16 -2(2) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.842(4)
2 0.158(4)
