Modulation of supramolecular self-assembly of BODIPY tectons via halogen bonding
Özcan, Emrah; Dedeoglu, Burcu; Chumakov, Yurii; Zorlu, Yunus; Çoşut, Bünyemin; Ayhan, Mehmet Menaf; CrystEngComm 23 (2021) 6365–6375; doi:10.1039/D1CE00862E

data_7243305
_publ_section_title
;
 Modulation of supramolecular self-assembly of BODIPY tectons via halogen
 bonding
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              6365
_journal_page_last               6375
_journal_paper_doi               10.1039/D1CE00862E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C24 H21 B F2 I N3'
_chemical_formula_sum            'C24 H21 B F2 I N3'
_chemical_formula_weight         527.15
_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
_audit_creation_date             2020-05-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-12-03 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                64.677(3)
_cell_angle_beta                 83.593(3)
_cell_angle_gamma                75.477(3)
_cell_formula_units_Z            4
_cell_length_a                   10.8154(6)
_cell_length_b                   15.2133(9)
_cell_length_c                   16.0136(8)
_cell_measurement_reflns_used    2354
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.45
_cell_volume                     2305.5(2)
_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)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1442
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34116
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.407
_exptl_absorpt_coefficient_mu    1.420
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker,2014/5)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.989
_refine_diff_density_min         -0.960
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     851
_refine_ls_number_reflns         8106
_refine_ls_number_restraints     1812
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0805
_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/[\s^2^(Fo^2^)+(0.0678P)^2^+18.3519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2111
_refine_ls_wR_factor_ref         0.2206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5651
_reflns_number_total             8106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00862e2.cif
_cod_data_source_block           18gtu177_bc_eo_58_0m_a-b3
_cod_depositor_comments
'Adding full bibliography for 7243304--7243306.cif.'
_cod_database_code               7243305
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.692
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N9-C64 = N9-C63 = C63-C62 = C62-C61 = C65-C61 = C65-C64
 1.35 with sigma of 0.001
 I3-C60 \\sim I2-C26
 with sigma of 0.02
 C72-C61 \\sim C28-C44
 with sigma of 0.04
 F5-B3 \\sim F4-B2
 with sigma of 0.02
 C61-C64 \\sim C44-C47
 with sigma of 0.04
 F6-B3 \\sim F3-B2
 with sigma of 0.02
 C60-C52 \\sim C26-C37
 with sigma of 0.04
 C67-C54 \\sim C33-C38
 with sigma of 0.04
 C68-C59 \\sim C32-C43
 with sigma of 0.04
 N7-C49 \\sim N4-C27
 with sigma of 0.02
 N7-C67 \\sim N4-C33
 with sigma of 0.02
 N7-B3 \\sim N4-B2
 with sigma of 0.02
 C57-C59 \\sim C41-C43
 with sigma of 0.04
 N8-C69 \\sim N5-C31
 with sigma of 0.02
 N8-C72 \\sim N5-C28
 with sigma of 0.02
 C63-C64 \\sim C46-C47
 with sigma of 0.04
 N8-B3 \\sim N5-B2
 with sigma of 0.02
 N9-C63 \\sim N6-C46
 with sigma of 0.02
 N9-C64 \\sim N6-C47
 with sigma of 0.02
 C49-C60 \\sim C27-C26
 with sigma of 0.02
 C49-C53 \\sim C27-C36
 with sigma of 0.02
 C69-C72 \\sim C31-C28
 with sigma of 0.04
 C71-C50 \\sim C29-C35
 with sigma of 0.04
 C60-C66 \\sim C26-C25
 with sigma of 0.02
 C66-C67 \\sim C25-C33
 with sigma of 0.02
 C49-C67 \\sim C27-C33
 with sigma of 0.04
 C66-C52 \\sim C25-C37
 with sigma of 0.02
 C66-C68 \\sim C25-C32
 with sigma of 0.04
 C67-C68 \\sim C33-C32
 with sigma of 0.02
 C67-C69 \\sim C33-C31
 with sigma of 0.04
 C68-C69 \\sim C32-C31
 with sigma of 0.02
 C68-C54 \\sim C32-C38
 with sigma of 0.02
 C68-C70 \\sim C32-C30
 with sigma of 0.04
 C69-C70 \\sim C31-C30
 with sigma of 0.02
 C69-C54 \\sim C31-C38
 with sigma of 0.04
 C70-C61 \\sim C30-C44
 with sigma of 0.04
 C70-C71 \\sim C30-C29
 with sigma of 0.02
 C70-C51 \\sim C30-C34
 with sigma of 0.02
 C71-C62 \\sim C29-C45
 with sigma of 0.04
 C71-C72 \\sim C29-C28
 with sigma of 0.02
 C71-C61 \\sim C29-C44
 with sigma of 0.02
 C72-C50 \\sim C28-C35
 with sigma of 0.02
 C54-C58 \\sim C38-C42
 with sigma of 0.04
 C55-C59 \\sim C39-C43
 with sigma of 0.04
 C54-C55 \\sim C38-C39
 with sigma of 0.02
 C54-C59 \\sim C38-C43
 with sigma of 0.02
 C55-C56 \\sim C39-C40
 with sigma of 0.02
 C49-C66 \\sim C27-C25
 with sigma of 0.04
 C49-B3 \\sim C27-B2
 with sigma of 0.04
 C56-C57 \\sim C40-C41
 with sigma of 0.02
 C57-C58 \\sim C41-C42
 with sigma of 0.02
 C60-C67 \\sim C26-C33
 with sigma of 0.04
 C60-C53 \\sim C26-C36
 with sigma of 0.04
 C58-C59 \\sim C42-C43
 with sigma of 0.02
 C67-C52 \\sim C33-C37
 with sigma of 0.04
 C67-B3 \\sim C33-B2
 with sigma of 0.04
 C61-C62 \\sim C44-C45
 with sigma of 0.02
 C61-C65 \\sim C44-C48
 with sigma of 0.02
 C62-C63 \\sim C45-C46
 with sigma of 0.02
 C68-C55 \\sim C32-C39
 with sigma of 0.04
 C64-C65 \\sim C47-C48
 with sigma of 0.02
 C69-C71 \\sim C31-C29
 with sigma of 0.04
 C69-C51 \\sim C31-C34
 with sigma of 0.04
 C69-B3 \\sim C31-B2
 with sigma of 0.04
 C70-C72 \\sim C30-C28
 with sigma of 0.04
 I3-C49 \\sim I2-C27
 with sigma of 0.04
 I3-C66 \\sim I2-C25
 with sigma of 0.04
 C71-C51 \\sim C29-C34
 with sigma of 0.04
 C71-C65 \\sim C29-C48
 with sigma of 0.04
 C72-B3 \\sim C28-B2
 with sigma of 0.04
 F5-F6 \\sim F4-F3
 with sigma of 0.04
 F5-N7 \\sim F4-N4
 with sigma of 0.04
 F5-N8 \\sim F4-N5
 with sigma of 0.04
 F6-N7 \\sim F3-N4
 with sigma of 0.04
 F6-N8 \\sim F3-N5
 with sigma of 0.04
 C54-C56 \\sim C38-C40
 with sigma of 0.04
 N7-N8 \\sim N4-N5
 with sigma of 0.04
 N7-C60 \\sim N4-C26
 with sigma of 0.04
 C55-C57 \\sim C39-C41
 with sigma of 0.04
 N7-C66 \\sim N4-C25
 with sigma of 0.04
 N7-C68 \\sim N4-C32
 with sigma of 0.04
 N7-C53 \\sim N4-C36
 with sigma of 0.04
 C56-C58 \\sim C40-C42
 with sigma of 0.04
 N8-C68 \\sim N5-C32
 with sigma of 0.04
 N8-C70 \\sim N5-C30
 with sigma of 0.04
 C61-C63 \\sim C44-C46
 with sigma of 0.04
 N8-C71 \\sim N5-C29
 with sigma of 0.04
 N8-C50 \\sim N5-C35
 with sigma of 0.04
 C62-C65 \\sim C45-C48
 with sigma of 0.04
 N9-C62 \\sim N6-C45
 with sigma of 0.04
 N9-C65 \\sim N6-C48
 with sigma of 0.04
3. Restrained planarity
 N6, C44, C45, C46, C47, C48
 with sigma of 0.1
 C38, C39, C40, C41, C42, C43
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.08 within 1.7A
All non-hydrogen atoms have similar U: within 2A with sigma of 0.05 and sigma
for terminal atoms of 0.1 within 2A
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 I3, F5, F6, N7, N8, N9, C49, C50, C51, C52, C53, C54, C55, C56, C57, C58, C59,
  C60, C61, C62, C63, C64, C65, C66, C67, C68, C69, C70, C71, C72, B3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 I2, F3, F4, N4, N5, N6, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35,
  C36, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46, C47, C48, B2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Sof(I2)=Sof(F3)=Sof(F4)=Sof(N4)=Sof(N5)=Sof(N6)=Sof(C25)=Sof(C26)=Sof(C27)=
 Sof(C28)=Sof(C29)=Sof(C30)=Sof(C31)=Sof(C32)=Sof(C33)=Sof(C34)=Sof(H34A)=
 Sof(H34B)=Sof(H34C)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C36)=Sof(H36A)=
 Sof(H36B)=Sof(H36C)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=Sof(C38)=Sof(C39)=
 Sof(H39)=Sof(C40)=Sof(H40)=Sof(C41)=Sof(H41)=Sof(C42)=Sof(H42)=Sof(C43)=
 Sof(H43)=Sof(C44)=Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=Sof(C47)=Sof(H47)=
 Sof(C48)=Sof(H48)=Sof(B2)=1-FVAR(1)
 Sof(I3)=Sof(F5)=Sof(F6)=Sof(N7)=Sof(N8)=Sof(N9)=Sof(C49)=Sof(C50)=Sof(H1)=
 Sof(H2)=Sof(H3)=Sof(C51)=Sof(H4)=Sof(H5)=Sof(H6)=Sof(C52)=Sof(H7)=Sof(H8)=
 Sof(H9)=Sof(C53)=Sof(H10)=Sof(H11)=Sof(H12)=Sof(C54)=Sof(C55)=Sof(H13)=
 Sof(C56)=Sof(H14)=Sof(C57)=Sof(H19)=Sof(C58)=Sof(H1A)=Sof(C59)=Sof(H1B)=
 Sof(C60)=Sof(C61)=Sof(C62)=Sof(H1C)=Sof(C63)=Sof(H1D)=Sof(C64)=Sof(H1E)=
 Sof(C65)=Sof(H1F)=Sof(C66)=Sof(C67)=Sof(C68)=Sof(C69)=Sof(C70)=Sof(C71)=
 Sof(C72)=Sof(B3)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C45(H45),
  C46(H46), C47(H47), C48(H48), C55(H13), C56(H14), C57(H19), C58(H1A),
 C59(H1B), C62(H1C), C63(H1D), C64(H1E), C65(H1F)
7.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,
 H37B,H37C), C50(H1,H2,H3), C51(H4,H5,H6), C52(H7,H8,H9), C53(H10,H11,H12)
;
_shelx_res_checksum              68992
_shelx_hkl_checksum              97951
_olex2_submission_special_instructions 'No special instructions were received'