Design of functionalized β-ketoenole derivatives as efficient fluorescent dyes for detection of amyloid fibrils
Kovalska, Vladyslava; Chernii, Svitlana; Losytskyy, Mykhaylo; Tretyakova, Iryna; Dovbii, Yan; Gorski, Alexandr; Chernii, Victor; Czerwieniec, Rafal; Yarmoluk, Sergiy; New Journal of Chemistry 42 (2018) 13308–; doi:10.1039/C8NJ01020J

data_7057560
_publ_section_title
;
 Design of functionalized \b-ketoenole derivatives as efficient
 fluorescent dyes for detection of amyloid fibrils
;
_journal_issue                   16
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13308
_journal_paper_doi               10.1039/C8NJ01020J
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         '2(C24 H27 N O3)'
_chemical_formula_sum            'C48 H54 N2 O6'
_chemical_formula_weight         754.93
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-10
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.10.04 svn.r3343 for OlexSys, GUI svn.r5250)
;
_audit_update_record
;
2017-10-14 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.5190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.0779(2)
_cell_length_b                   7.22350(10)
_cell_length_c                   25.3699(3)
_cell_measurement_reflns_used    32994
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.4010
_cell_measurement_theta_min      5.0980
_cell_volume                     4033.41(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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      4.00  33.00   1.00    3.50    --   40.00  88.00-114.76   29
  2  \w      3.00  32.00   1.00    3.50    --   40.00  90.00  94.75   29
  3  \w   -116.00 -17.00   1.00    3.50    --  -41.23 -37.00-150.00   99
  4  \w   -116.00 -17.00   1.00    3.50    --  -41.23 -37.00 -60.00   99
  5  \w   -116.00 -17.00   1.00    3.50    --  -41.23 -37.00 120.00   99
  6  \w    -97.00  -2.00   1.00    3.50    --  -41.23 125.00 -60.00   95
  7  \w   -114.00 -13.00   1.00    3.50    --  -41.23 -57.00  60.00  101
  8  \w      2.00  97.00   1.00    3.50    --   41.23-125.00-150.00   95
  9  \w      7.00  33.00   1.00    3.50    --   44.00  89.00 -24.26   26
 10  \w      7.00  33.00   1.00    3.50    --   44.00  89.00-173.86   26
 11  \w     18.00  45.00   1.00    3.50    --   52.00  82.00  -8.09   27
 12  \w     23.00 132.00   1.00    3.50    --   56.00  77.00 -43.26  109
 13  \w     23.00  49.00   1.00    3.50    --   56.00  78.00-102.16   26
 14  \w     32.00 140.00   1.00    3.50    --   64.00  76.00-173.65  108
 15  \w     31.00 140.00   1.00    3.50    --   64.00  77.00 110.60  109
 16  \w     31.00 140.00   1.00    3.50    --   64.00  77.00 148.82  109
 17  \w     36.00 143.00   1.00    3.50    --   68.00  75.00  63.30  107
 18  \w     35.00 144.00   1.00    3.50    --   68.00  77.00-160.04  109
 19  \w     35.00 144.00   1.00    3.50    --   68.00  77.00  25.12  109
 20  \w     35.00 144.00   1.00    3.50    --   68.00  77.00  25.12  109
 21  \w     39.00 148.00   1.00    3.50    --   72.00  77.00-119.39  109
 22  \w     74.00 158.00   1.00   30.00    --  106.46  77.00 150.00   84
 23  \w     74.00 158.00   1.00   30.00    --  106.46  77.00  30.00   84
 24  \w     74.00 158.00   1.00   30.00    --  106.46  77.00 -60.00   84
 25  \w     77.00 158.00   1.00   30.00    --  106.46  61.00  90.00   81
 26  \w     34.00 136.00   1.00   30.00    --  106.46 -61.00-180.00  102
 27  \w     77.00 158.00   1.00   30.00    --  106.46  61.00  60.00   81
 28  \w     74.00 158.00   1.00   30.00    --  106.46  77.00 -30.00   84
 29  \w     74.00 158.00   1.00   30.00    --  106.46  77.00-120.00   84
 30  \w     77.00 158.00   1.00   30.00    --  106.46  61.00 120.00   81
 31  \w     24.00 109.00   1.00   30.00    --  106.46 -94.00 -90.00   85
 32  \w     24.00 109.00   1.00   30.00    --  106.46 -94.00  60.00   85
 33  \w     74.00 158.00   1.00   30.00    --  106.46  77.00   0.00   84
 34  \w     77.00 109.00   1.00   30.00    --  106.46  61.00   0.00   32
 35  \w     74.00 142.00   1.00   30.00    --  106.46  77.00-180.00   68
 36  \w     74.00 154.00   1.00   30.00    --  106.46  77.00  60.00   80
 37  \w     24.00  98.00   1.00   30.00    --  106.46 -94.00   0.00   74
 38  \w     74.00 150.00   1.00   30.00    --  106.46  77.00 -90.00   76
 39  \w     74.00 144.00   1.00   30.00    --  106.46  77.00 120.00   70
 40  \w     42.00  71.00   1.00   30.00    --  106.46 -45.00  30.00   29
 41  \w     34.00 101.00   1.00   30.00    --  106.46 -94.00 120.00   67
 42  \w     39.00  77.00   1.00   30.00    --  106.46 -45.00 -30.00   38
 43  \w     78.00 103.00   1.00   30.00    --  106.46  61.00 -90.00   25
 44  \w     74.00 154.00   1.00   30.00    --  106.46  77.00-150.00   80
 45  \w     39.00 109.00   1.00   30.00    --  106.46 -94.00-180.00   70
 46  \w     74.00 101.00   1.00   30.00    --  106.46  77.00  90.00   27
 47  \w     88.00 121.00   1.00   30.00    --  106.46-125.00   0.00   33
 48  \w     78.00 136.00   1.00   30.00    --  106.46  61.00 150.00   58
 49  \w     40.00  68.00   1.00   30.00    --  106.46 -45.00  90.00   28
 50  \w     33.00  81.00   1.00   30.00    --  106.46-125.00   0.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0473925000
_diffrn_orient_matrix_UB_12      -0.0001291000
_diffrn_orient_matrix_UB_13      -0.0479375000
_diffrn_orient_matrix_UB_21      -0.0508864000
_diffrn_orient_matrix_UB_22      0.0334125000
_diffrn_orient_matrix_UB_23      0.0371146000
_diffrn_orient_matrix_UB_31      0.0080522000
_diffrn_orient_matrix_UB_32      0.2106159000
_diffrn_orient_matrix_UB_33      -0.0059152000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            86784
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.556
_diffrn_reflns_theta_min         3.495
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       plate
_exptl_crystal_F_000             1616
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         8076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0480P)^2^+1.2437P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6959
_reflns_number_total             8076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01020j2.cif
_cod_data_source_block           p148
_cod_depositor_comments
'Adding full bibliography for 7057559--7057560.cif.'
_cod_database_code               7057560
_chemical_oxdiff_formula         'C24 H27 N1 O3'
_chemical_oxdiff_usercomment     Czerwieniec_Y-05
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C46(H46A,H46B), C47(H47A,H47B), C23(H23A,H23B), C39(H39A,
 H39B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C29(H29), C34(H34), C38(H38), C27(H27), C13(H13), C10(H10),
 C11(H11), C14(H14), C32(H32), C5(H5A), C31(H31), C37(H37), C35(H35), C7(H7),
 C3(H3), C8(H8), C45(H45), C41(H41), C44(H44), C17(H17), C21(H21), C42(H42),
 C43(H43), C20(H20), C19(H19), C18(H18)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C48(H48A,H48B,H48C), C24(H24A,H24B,H24C), C2(H2B,H2C,H2D)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O5(H5)
;
_shelx_res_checksum              10611
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-10-06
_olex2_date_sample_submission    2016-09-30
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id Y-05
_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 1.161
_oxdiff_exptl_absorpt_empirical_full_min 0.866