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_7160886
_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 H21 N5'
_chemical_formula_sum            'C30 H21 N5'
_chemical_formula_weight         451.52
_chemical_name_common            'beta-2-pyridyl aza-dipyrrin'
_chemical_name_systematic
N-[5-phenyl-3-(2-pyridyl)-2H-pyrrol-2-ylidene]-3-(2-pyridyl)-1H-pyrrol-2-amine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-07
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-10-09 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.447(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1073(11)
_cell_length_b                   13.2874(12)
_cell_length_c                   15.8308(15)
_cell_measurement_reflns_used    6013
_cell_measurement_temperature    200.05
_cell_measurement_theta_max      26.392
_cell_measurement_theta_min      2.43
_cell_volume                     2272.4(4)
_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      200.05
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.976
_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  0.0494
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21707
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.024
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0961 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.8430.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic bluish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_preparation
'Attempted reaction of bis-(beta-2-pyridyl)azaBODIPY with Er(hfac)3(H2O)2'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Diffusion of MTBE vapour into a saturated acetone solution of crude product mixture'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0627P)^2^+0.7601P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2740
_reflns_number_total             4530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01628b2.cif
_cod_data_source_block           k1188_0m_a
_cod_database_code               7160886
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H) groups
2. Restrained distances
 N1-H1A \\sim N3-H1B
 with sigma of 0.02
3. Others
 Sof(H1B)=1-FVAR(1)
 Sof(H1A)=FVAR(1)
4.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              43142
_olex2_date_sample_data_collection 2022-05-15
_olex2_date_sample_submission    2022-05-14
_olex2_exptl_crystal_mounting_method 'Mounted on a 100 uM MicroLoop'
_olex2_submission_original_sample_id K1188-RDB1
_olex2_submission_special_instructions 'No special instructions were received'