Reactivity of an aza-dipyrrin and an aza-BODIPY motif bearing two 2-pyridyl units: an emissive NNN binding pocket.
Gapare, Rosinah Liandrah; Diaz-Rodriguez, Roberto M; Williams, Victoria A.; Atwood, Mark; Cotnam, Michael J.; Hilborn, James W.; Johnson, Erin R.; Robertson, Katherine N.; Thompson, Alison; Organic & biomolecular chemistry 23 (2025) 10391–10397; doi:10.1039/d5ob01628b

data_7160887
_publ_section_title
;
 Reactivity of an aza-dipyrrin and an aza-BODIPY motif bearing two
 2-pyridyl units: an emissive NNN binding pocket.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10391
_journal_page_last               10397
_journal_paper_doi               10.1039/d5ob01628b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C30 H20 B F2 N5'
_chemical_formula_sum            'C30 H20 B F2 N5'
_chemical_formula_weight         499.32
_chemical_name_common            'beta-2-pyridyl aza-BODIPY'
_chemical_name_systematic
(4,4)-Difluoro[5-phenyl-N-[5-phenyl-3-(2-pyridyl)-2H-pyrrol-2-ylidene-kN]-3-(2-pyridyl)-1H-pyrrol-2-aminato-kN1]boron
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-10-09 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.8670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4995(8)
_cell_length_b                   7.0430(4)
_cell_length_c                   23.6436(13)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    208.15
_cell_measurement_theta_max      28.268
_cell_measurement_theta_min      2.49
_cell_volume                     2362.9(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      208.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            47836
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.435
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0757 before and 0.0449 after correction.
The Ratio of minimum to maximum transmission is 0.9684.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic greenish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       Block
_exptl_crystal_F_000             1032
_exptl_crystal_recrystallization_method
'Grown via slow diffusion of hexanes layered on a saturated dichloromethane solution at 2 degC'
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.174
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.7101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4690
_reflns_number_total             5878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01628b2.cif
_cod_data_source_block           s1114_0m_a
_cod_database_code               7160887
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30)
;
_shelx_res_checksum              90299
_olex2_date_sample_data_collection 2022-03-23
_olex2_date_sample_submission    2022-03-23
_olex2_exptl_crystal_mounting_method
'Mounted on a 200 uM MicroLoop with Parabar 10312 oil'
_olex2_submission_original_sample_id RDB3_S1114
_olex2_submission_special_instructions 'No special instructions were received'