Fusion of pyrene and phenanthrene through 5<i>H</i>-imidazo[1,2-<i>a</i>]azepine scaffolds: structural tuning for fluorescence labeling and bacterial imaging.
Qiu, Nicholas P.; Eradeh, Ramin; Britt, Liam H.; Zhao, Yuming; Physical chemistry chemical physics : PCCP 28 (2026) 5880–5893; doi:10.1039/d5cp02942b

data_7251613
_publ_section_title
;
 Fusion of pyrene and phenanthrene through
 5<i>H</i>-imidazo[1,2-<i>a</i>]azepine scaffolds: structural tuning for
 fluorescence labeling and bacterial imaging.
;
_journal_issue                   9
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              5880
_journal_page_last               5893
_journal_paper_doi               10.1039/d5cp02942b
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C18 H B F15 O, C32 H17 N2 O'
_chemical_formula_sum            'C50 H18 B F15 N2 O2'
_chemical_formula_weight         974.47
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2mkyhn
_audit_creation_date             2024-05-15
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-03-10 deposited with the CCDC.	2026-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.4280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.61620(10)
_cell_length_b                   7.91840(10)
_cell_length_c                   30.8317(3)
_cell_measurement_reflns_used    18671
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.1950
_cell_measurement_theta_min      2.8400
_cell_volume                     3780.51(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.120a (release 16-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -121.00 -32.00   0.50   18.01    --  -47.13 -38.00 -45.00  178
  2  \w    -35.00  27.00   0.50   18.01    --  -47.13  38.00 108.00  124
  3  \w    -26.00  49.00   0.50   18.01    --   47.13 -38.00 -45.00  150
  4  \w     33.00 121.00   0.50   18.01    --   47.13  38.00 108.00  176
  5  \w   -165.00 -77.00   0.50   72.06    --  -91.75 -38.00 -45.00  176
  6  \w     99.00 178.00   0.50   72.06    --  113.25  38.00 108.00  158
  7  \w    -16.00  28.00   0.50   18.01    --  -47.13  19.00 -30.00   88
  8  \w    -16.00  28.00   0.50   18.01    --  -47.13  19.00  90.00   88
  9  \w    -16.00  28.00   0.50   18.01    --  -47.13  19.00-120.00   88
 10  \w    -85.00 -22.00   0.50   72.06    --  -91.75 125.00 150.00  126
 11  \w    -65.00 -19.00   0.50   72.06    --  -91.75  61.00-150.00   92
 12  \w     41.00  79.00   0.50   72.06    --  113.25 -61.00  30.00   76
 13  \w     41.00  79.00   0.50   72.06    --  113.25 -61.00-180.00   76
 14  \w     41.00  79.00   0.50   72.06    --  113.25 -61.00 -30.00   76
 15  \w     41.00  79.00   0.50   72.06    --  113.25 -61.00   0.00   76
 16  \w     41.00 137.00   0.50   72.06    --  113.25 -77.00-120.00  192
 17  \w     99.00 178.00   0.50   72.06    --  113.25  30.00-120.00  158
 18  \w     41.00  79.00   0.50   72.06    --  113.25 -61.00 -90.00   76
 19  \w     41.00  79.00   0.50   72.06    --  113.25 -61.00  90.00   76
 20  \w     99.00 178.00   0.50   72.06    --  113.25  45.00-180.00  158
 21  \w     96.00 178.00   0.50   72.06    --  113.25  61.00-150.00  164
 22  \w     41.00 137.00   0.50   72.06    --  113.25 -77.00-120.00  192
 23  \w     96.00 178.00   0.50   72.06    --  113.25  61.00 120.00  164
 24  \w     95.00 178.00   0.50   72.06    --  113.25 125.00  30.00  166
 25  \w     95.00 178.00   0.50   72.06    --  113.25 125.00  30.00  166
 26  \w     41.00 106.00   0.50   72.06    --  113.25 -94.00  60.00  130
 27  \w     99.00 178.00   0.50   72.06    --  113.25  45.00 -30.00  158
 28  \w     41.00 106.00   0.50   72.06    --  113.25 -94.00-150.00  130
 29  \w     41.00 106.00   0.50   72.06    --  113.25 -94.00  90.00  130
 30  \w     41.00  79.00   0.50   72.06    --  113.25 -61.00 120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0803870000
_diffrn_orient_matrix_UB_12      0.0809208000
_diffrn_orient_matrix_UB_13      -0.0156094000
_diffrn_orient_matrix_UB_21      0.0336261000
_diffrn_orient_matrix_UB_22      0.0494986000
_diffrn_orient_matrix_UB_23      0.0474836000
_diffrn_orient_matrix_UB_31      0.0479823000
_diffrn_orient_matrix_UB_32      -0.1698859000
_diffrn_orient_matrix_UB_33      0.0064025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            49661
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.706
_diffrn_reflns_theta_min         2.854
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.120a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_description       prism
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         8087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0525P)^2^+2.7286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6676
_reflns_number_total             8087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp02942b2.cif
_cod_data_source_block           lb-01-007
_cod_depositor_comments
'Adding full bibliography for 7251612--7251614.cif.'
_cod_database_code               7251613
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C50H17BF16N2O
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.891
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29)
;
_shelx_res_checksum              55648
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.832