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_7057559
_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_absolute_configuration ad
_chemical_formula_moiety         'C17 H21 N O3'
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-10-19
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.10.10 svn.r3347 for OlexSys, GUI svn.r5252)
;
_audit_update_record
;
2017-10-14 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0221(2)
_cell_length_b                   8.5085(2)
_cell_length_c                   23.2424(4)
_cell_measurement_reflns_used    7013
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.4310
_cell_measurement_theta_min      3.7490
_cell_volume                     1586.43(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.23t (Agilent, 2014)'
_computing_data_collection       'CrysAlisPro 1.171.38.23t (Agilent, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.38.23t (Agilent, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (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   -116.00 -17.00   1.00    5.00    --  -41.23 -37.00-120.00   99
  2  \w   -114.00 -13.00   1.00    5.00    --  -41.23 -57.00 150.00  101
  3  \w    -69.00  32.00   1.00    5.00    --  -41.23  57.00 -60.00  101
  4  \w     30.00 139.00   1.00   25.00    --  106.46 -77.00-180.00  109
  5  \w     33.00 121.00   1.00   25.00    --  106.46-125.00  60.00   88
  6  \w     30.00 139.00   1.00   25.00    --  106.46 -77.00  30.00  109
  7  \w     77.00 158.00   1.00   25.00    --  106.46  61.00   0.00   81
  8  \w     32.00 137.00   1.00   25.00    --  106.46-154.00  51.00  105
  9  \w     33.00  77.00   1.00   25.00    --  106.46 -45.00  30.00   44
 10  \w     33.00 121.00   1.00   25.00    --  106.46-125.00-150.00   88
 11  \w     54.00 158.00   1.00   25.00    --  106.46  15.00-150.00  104
 12  \w     30.00  69.00   1.00   25.00    --  106.46 -30.00   0.00   39
 13  \w     74.00 158.00   1.00   25.00    --  106.46  77.00  30.00   84
 14  \w   -117.00  -9.00   1.00    5.00    --  -41.23 -77.00 120.00  108
 15  \w   -117.00  -9.00   1.00    5.00    --  -41.23 -77.00  30.00  108
 16  \w    -97.00  -2.00   1.00    5.00    --  -41.23 125.00  60.00   95
 17  \w     81.00 158.00   1.00   25.00    --  106.46  45.00-120.00   77
 18  \w     77.00 158.00   1.00   25.00    --  106.46  61.00  90.00   81
 19  \w     81.00 144.00   1.00   25.00    --  106.46  45.00 -30.00   63
 20  \w     78.00 158.00   1.00   25.00    --  106.46  30.00 -60.00   80
;
_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      0.0197267000
_diffrn_orient_matrix_UB_12      -0.0557544000
_diffrn_orient_matrix_UB_13      0.0626899000
_diffrn_orient_matrix_UB_21      -0.0299514000
_diffrn_orient_matrix_UB_22      -0.1709643000
_diffrn_orient_matrix_UB_23      -0.0192637000
_diffrn_orient_matrix_UB_31      0.1885988000
_diffrn_orient_matrix_UB_32      -0.0215952000
_diffrn_orient_matrix_UB_33      -0.0096108000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16588
_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         73.410
_diffrn_reflns_theta_min         3.804
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.23t (Agilent, 2014)
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    1.203
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0411P)^2^+0.1696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2903
_reflns_number_total             3165
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01020j2.cif
_cod_data_source_block           exp_185_pl
_cod_depositor_comments
'Adding full bibliography for 7057559--7057560.cif.'
_cod_database_code               7057559
_chemical_oxdiff_formula         'C17 H21 N O3'
_chemical_oxdiff_usercomment     Czerwieniec_YAN166
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(2) 0.1(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C7(H7A), C5(H5), C8(H8), C2(H2), C6(H6), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              4961
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-10-18
_olex2_date_sample_submission    2016-10-12
_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 'YAN 156'
_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 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.762