Highly tunable bimane-based fluorescent probes: design, synthesis, and application as a selective amyloid binding dye.
Venkatesh, Yarra; Marotta, Nicholas P.; Lee, Virginia M.-Y.; Petersson, E. James; Chemical science 15 (2024) 6053–6063; doi:10.1039/d4sc00024b

data_1571295
_publ_section_title
;
 Highly tunable bimane-based fluorescent probes: design, synthesis, and
 application as a selective amyloid binding dye.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              6053
_journal_page_last               6063
_journal_paper_doi               10.1039/d4sc00024b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C17 H15 F N2 O2, 0.125(H2 O)'
_chemical_formula_sum            'C17 H15.25 F N2 O2.125'
_chemical_formula_weight         300.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-04
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2024-01-04 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   29.9395(3)
_cell_length_b                   27.5788(3)
_cell_length_c                   7.07968(9)
_cell_measurement_reflns_used    25458
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.3230
_cell_measurement_theta_min      2.9490
_cell_volume                     5845.66(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -24.00  63.00   0.50    2.00    --   47.04 -59.00  90.00  174
  2  \w     31.00 120.00   0.50    2.00    --   47.04  59.00-128.00  178
  3  \w   -159.00 -70.00   0.50    8.00    --  -86.25 -59.00  90.00  178
  4  \w    -71.00 -14.00   0.50    8.00    --  -86.25  59.00-128.00  114
  5  \w     35.00  65.00   0.50    8.00    --  107.75 -59.00  90.00   60
  6  \w     92.00 178.00   0.50    8.00    --  107.75  59.00-128.00  172
  7  \w    -30.00  28.00   0.50    2.00    --  -47.04  19.00  30.00  116
  8  \w    -30.00  28.00   0.50    2.00    --  -47.04  19.00-180.00  116
  9  \w    -30.00  28.00   0.50    2.00    --  -47.04  19.00-120.00  116
 10  \w    -63.00  25.00   0.50    2.00    --  -47.04  59.00-128.00  176
 11  \w   -118.00 -31.00   0.50    2.00    --  -47.04 -59.00  90.00  174
 12  \w    -25.00  70.00   0.50    2.00    --   47.04 -77.00-180.00  190
 13  \w    -74.00 -13.00   0.50    8.00    --  -86.25  61.00  30.00  122
 14  \w    -38.00 -11.00   0.50    8.00    --  -86.25  30.00   0.00   54
 15  \w     35.00 132.00   0.50    8.00    --  107.75 -79.00  69.59  194
 16  \w     35.00  68.00   0.50    8.00    --  107.75 -61.00 -60.00   66
 17  \w     94.00 178.00   0.50    8.00    --  107.75  15.00 -90.00  168
 18  \w     35.00 103.00   0.50    8.00    --  107.75 -77.00   0.00  136
 19  \w     35.00 132.00   0.50    8.00    --  107.75 -80.00-142.39  194
 20  \w     91.00 178.00   0.50    8.00    --  107.75  61.00-180.00  174
 21  \w     35.00 132.00   0.50    8.00    --  107.75 -80.00 -72.43  194
 22  \w     35.00  68.00   0.50    8.00    --  107.75 -61.00   0.00   66
 23  \w     95.00 178.00   0.50    8.00    --  107.75  30.00   0.00  166
 24  \w     95.00 178.00   0.50    8.00    --  107.75  30.00 -60.00  166
 25  \w     35.00  68.00   0.50    8.00    --  107.75 -61.00  60.00   66
 26  \w     95.00 178.00   0.50    8.00    --  107.75  45.00 -90.00  166
 27  \w     35.00 132.00   0.50    8.00    --  107.75 -80.00  27.20  194
 28  \w     35.00  68.00   0.50    8.00    --  107.75 -61.00 150.00   66
 29  \w     95.00 178.00   0.50    8.00    --  107.75  45.00  60.00  166
 30  \w     35.00 103.00   0.50    8.00    --  107.75 -77.00 -90.00  136
 31  \w     85.00 178.00   0.50    8.00    --  107.75  77.00 120.00  186
 32  \w     35.00 103.00   0.50    8.00    --  107.75 -77.00-180.00  136
 33  \w     35.00 103.00   0.50    8.00    --  107.75 -77.00 150.00  136
 34  \w     35.00  68.00   0.50    8.00    --  107.75 -61.00-150.00   66
 35  \w     95.00 178.00   0.50    8.00    --  107.75  30.00  60.00  166
 36  \w     35.00 132.00   0.50    8.00    --  107.75 -80.00 120.93  194
 37  \w     35.00 103.00   0.50    8.00    --  107.75 -77.00 -60.00  136
 38  \w     35.00 103.00   0.50    8.00    --  107.75 -77.00 -30.00  136
 39  \w     35.00 103.00   0.50    8.00    --  107.75 -77.00  30.00  136
 40  \w     35.00 132.00   0.50    8.00    --  107.75 -80.00-100.39  194
 41  \w     35.00 132.00   0.50    8.00    --  107.75 -80.00 151.11  194
 42  \w     35.00 132.00   0.50    8.00    --  107.75 -79.00-159.50  194
 43  \w     95.00 178.00   0.50    8.00    --  107.75  45.00 150.00  166
 44  \w   -119.00 -24.00   0.50    2.00    --  -47.04 -77.00   0.00  190
 45  \w   -118.00 -32.00   0.50    2.00    --  -47.04 -57.00 -90.00  172
 46  \w   -119.00 -24.00   0.50    2.00    --  -47.04 -77.00  60.00  190
 47  \w     24.00 120.00   0.50    2.00    --   47.04  77.00 150.00  192
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0339910000
_diffrn_orient_matrix_UB_12      -0.0416122000
_diffrn_orient_matrix_UB_13      0.0208038000
_diffrn_orient_matrix_UB_21      0.0117558000
_diffrn_orient_matrix_UB_22      -0.0045253000
_diffrn_orient_matrix_UB_23      0.2111295000
_diffrn_orient_matrix_UB_31      -0.0367973000
_diffrn_orient_matrix_UB_32      0.0369825000
_diffrn_orient_matrix_UB_33      0.0485163000
_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  0.0563
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            35147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         4.359
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             2516
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0568P)^2^+4.6832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2938
_reflns_number_total             2976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00024b2.cif
_cod_data_source_block           99536
_cod_depositor_comments
'Adding full bibliography for 1571295--1571297.cif.'
_cod_original_cell_volume        5845.66(12)
_cod_database_code               1571295
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.820
_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, All O(H,H) groups
2. Others
 Fixed Sof: O18(0.125) H18A(0.125) H18B(0.125)
 Fixed X: H18A(0.51765) H18B(0.480539)
 Fixed Y: H18A(0.48566) H18B(0.51494)
 Fixed Z: H18A(1.10291) H18B(1.09311)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              54200
_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 1.938
_oxdiff_exptl_absorpt_empirical_full_min 0.505