Solid supported synthesis of pyrazinyl and oxindolyl tethered ferrocenyl conjugates with unusual rotational flexibility as promising inhibitors of HEWL amyloid fibrillation and cytotoxicity
Halder, Biplob; Mitra, Amit; Mishra, Ananya; Naik, Lincoln; Sarkar, Nandini; Dhiman, Rohan; Chatterjee, Saurav; New Journal of Chemistry 48 (2024) 19876–19899; doi:10.1039/D4NJ04116J

data_7063515
_publ_section_title
;
 Solid supported synthesis of pyrazinyl and oxindolyl tethered ferrocenyl
 conjugates with unusual rotational flexibility as promising inhibitors of
 HEWL amyloid fibrillation and cytotoxicity
;
_journal_issue                   47
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19876
_journal_page_last               19899
_journal_paper_doi               10.1039/D4NJ04116J
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C24 H18 Fe N4 O2'
_chemical_formula_sum            'C24 H18 Fe N4 O2'
_chemical_formula_weight         450.27
_chemical_name_systematic        FCDIPYR
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-10-31 deposited with the CCDC.	2024-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4065(5)
_cell_length_b                   11.8508(5)
_cell_length_c                   13.1663(7)
_cell_measurement_reflns_used    5807
_cell_measurement_temperature    278
_cell_measurement_theta_max      26.7230
_cell_measurement_theta_min      1.6300
_cell_volume                     1935.80(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      278
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.877
_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    -54.00 -27.00   0.50   38.85    --   10.00 -68.00  19.00   54
  2  \w    -27.00  -1.00   0.50   38.85    --   10.00 -68.00 151.00   52
  3  \w     16.00  41.00   0.50   38.85    --  -10.20  68.00 -75.00   50
  4  \w    -78.00  37.00   0.50   38.85    --   10.00 -38.00-150.00  230
  5  \w     -7.00  66.00   0.50   38.85    --   10.00  77.00  60.00  146
  6  \w    -32.00  -6.00   0.50   38.85    --  -10.20 -57.00-120.00   52
  7  \w    -35.00  11.00   0.50   38.85    --  -10.20  77.00-150.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0347829000
_diffrn_orient_matrix_UB_12      0.0474447000
_diffrn_orient_matrix_UB_13      -0.0024227000
_diffrn_orient_matrix_UB_21      -0.0275406000
_diffrn_orient_matrix_UB_22      -0.0246703000
_diffrn_orient_matrix_UB_23      -0.0417636000
_diffrn_orient_matrix_UB_31      -0.0360082000
_diffrn_orient_matrix_UB_32      -0.0269214000
_diffrn_orient_matrix_UB_33      0.0339674000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10717
_diffrn_reflns_point_group_measured_fraction_full 0.866
_diffrn_reflns_point_group_measured_fraction_max 0.745
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.859
_diffrn_reflns_theta_min         1.718
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_preparation       'SLOW EVAPORATION'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.036
_refine_diff_density_max         1.391
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0508P)^2^+0.5665P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.625
_reflns_Friedel_fraction_full    0.720
_reflns_Friedel_fraction_max     0.600
_reflns_number_gt                2888
_reflns_number_total             3438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj04116j2.cif
_cod_data_source_block           scfcdipyr_081221
_cod_depositor_comments
'Adding full bibliography for 7063513--7063515.cif.'
_cod_database_code               7063515
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H18 N4 O2 Fe'
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.861
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.88(3)
 0.12(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_original_sample_id SCFCDIPYR
_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 2.061
_oxdiff_exptl_absorpt_empirical_full_min 0.602