Conformational stabilization of isatin Schiff bases – biologically active chemical probes
Smirnov, Andrey S.; Nikolaev, Dmitriy N.; Gurzhiy, Vlad V.; Smirnov, Sergey N.; Suslonov, Vitaliy S.; Garabadzhiu, Alexander V.; Davidovich, Pavel B.; RSC Adv. 7 (2017) 10070–; doi:10.1039/C6RA26779C

data_7227635
_publ_section_title
;
 Conformational stabilization of isatin Schiff bases&#x00A0;--
 biologically active chemical probes
;
_journal_issue                   17
_journal_name_full               'RSC Adv.'
_journal_page_first              10070
_journal_paper_doi               10.1039/C6RA26779C
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C15 H12 N2 O, C9 H7 N O2'
_chemical_formula_sum            'C24 H19 N3 O3'
_chemical_formula_weight         397.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-09-22 deposited with the CCDC.
2017-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                85.8492(17)
_cell_angle_beta                 85.7112(18)
_cell_angle_gamma                69.989(2)
_cell_formula_units_Z            4
_cell_length_a                   7.8377(2)
_cell_length_b                   8.33995(19)
_cell_length_c                   31.7116(6)
_cell_measurement_reflns_used    21591
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9670
_cell_measurement_theta_min      5.5530
_cell_volume                     1939.84(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -51.00  -13.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   90.0000 38

  2 omega -111.00  -11.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -30.0000 100

  3 omega -114.00  -26.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -120.0000 88

  4 omega  -69.00   33.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000   30.0000 102

  5 omega -114.00  -69.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   90.0000 45

  6 omega -106.00  -53.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -163.0000   74.0834 53

  7 omega   55.00  126.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000    0.0000 71

  8 omega   55.00  129.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000 -150.0000 74

  9 omega   14.00   45.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000 -180.0000 31

 10 omega    8.00   35.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       44.0000   85.0000 -105.0699 27

 11 omega    7.00   32.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       44.0000   88.0000  -91.4038 25

 12 omega   12.00   37.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000   38.3692 25

 13 omega   22.00   48.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  162.5277 26

 14 omega   22.00   47.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  -37.9348 25

 15 omega   22.00   47.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  105.6922 25

 16 omega   31.00   57.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000   16.7745 26

 17 omega  121.00  146.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -28.9162 25

 18 omega   35.00   66.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000  -78.8325 31

 19 omega   35.00   63.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -28.9162 28

 20 omega   35.00   64.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000   45.9825 29

 21 omega   35.00   62.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  119.6347 27

 22 omega   35.00   63.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000 -159.3435 28

 23 omega   38.00   64.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000 -123.0666 26

 24 omega  110.00  136.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000  -78.8325 26

 25 omega   38.00   64.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000   87.6638 26

 26 omega   39.00   66.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       72.0000   76.0000  146.7777 27

 27 omega  123.00  153.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       76.0000   73.0000 -144.8218 30

 28 omega   44.00   70.00   1.0000    1.8800
omega____ theta____ kappa____ phi______ frames
    -       76.0000   73.0000 -144.8218 26

 29 omega   47.00   73.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       80.0000   73.0000  -20.9677 26

 30 omega   47.00   72.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       80.0000   76.0000  157.8323 25

 31 omega   58.00   84.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       88.0000   58.0000   45.1220 26

 32 omega   56.00   82.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       88.0000   70.0000   -6.1171 26

 33 omega   58.00   84.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       88.0000   62.0000  108.2330 26

 34 omega   58.00   84.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       88.0000   64.0000 -142.2332 26

 35 omega  138.00  164.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       92.0000   72.0000   40.1196 26

 36 omega   59.00  129.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       92.0000   72.0000   40.1196 70

 37 omega   62.00   87.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       92.0000   57.0000   92.3394 25

 38 omega   65.00  103.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       96.0000   66.0000  126.2527 38

 39 omega   68.00  115.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -       96.0000   64.0000  -61.1896 47

 40 omega   69.00   97.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      100.0000   66.0000  166.9621 28

 41 omega   76.00  123.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   69.0000 -114.5732 47

 42 omega   41.00   66.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 25

 43 omega   84.00  149.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   60.0000 65

 44 omega  117.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 60

 45 omega   36.00  115.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 79

 46 omega   79.00  105.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

 47 omega   39.00  115.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 76

 48 omega   82.00  168.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   73.0000 -134.6326 86

 49 omega   83.00  148.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 65

 50 omega   53.00   97.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 44

 51 omega   79.00  127.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 48

 52 omega  141.00  171.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 30

 53 omega   79.00  124.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 45

 54 omega  121.00  147.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 26

 55 omega   79.00  105.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 26

 56 omega   85.00  111.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 26

 57 omega  130.00  156.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

 58 omega   79.00  106.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 27

 59 omega   39.00   92.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 53

 60 omega   37.00   72.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 35

 61 omega  152.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 25

 62 omega   70.00  114.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 44

 63 omega  104.00  137.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 33

 64 omega   49.00  111.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 62

 65 omega   79.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 98

 66 omega   76.00  113.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 37

 67 omega   38.00   83.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 45

 68 omega   85.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 92

 69 omega   86.00  172.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 86

 70 omega   99.00  129.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 30

 71 omega   34.00   73.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  120.0000 39

 72 omega  102.00  165.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 63

 73 omega  109.00  135.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 26

 74 omega   54.00   89.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 35

 75 omega   88.00  178.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 90

 76 omega   79.00  106.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 27

 77 omega   83.00  152.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 69

 78 omega   48.00   97.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 49

 79 omega   79.00  125.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 46

 80 omega   85.00  143.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 58

 81 omega   80.00  176.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 96

 82 omega   88.00  115.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 27

 83 omega   46.00   72.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 26

 84 omega   83.00  177.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 94

 85 omega  142.00  170.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 28

 86 omega   84.00  134.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 50

 87 omega  140.00  165.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 25

 88 omega  110.00  157.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 47

 89 omega  121.00  170.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 49

 90 omega   79.00  106.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0981946000
_diffrn_orient_matrix_UB_12      0.1947404000
_diffrn_orient_matrix_UB_13      -0.0003700000
_diffrn_orient_matrix_UB_21      0.1386327000
_diffrn_orient_matrix_UB_22      0.0252383000
_diffrn_orient_matrix_UB_23      -0.0345959000
_diffrn_orient_matrix_UB_31      -0.1225709000
_diffrn_orient_matrix_UB_32      -0.0135458000
_diffrn_orient_matrix_UB_33      -0.0343838000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            46094
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.493
_diffrn_reflns_theta_min         2.798
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0178P)^2^+3.6448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1456
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7226
_reflns_number_total             7703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra26779c2.cif
_cod_data_source_block           Compound_4_lcb_007
_cod_original_cell_volume        1939.83(8)
_cod_database_code               7227635
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 94.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C24(H24), C25(H25), C26(H26), C27(H27), C6A(H6A), C7A(H7A), C8A(H8A),
  C9A(H9A), C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A),
 C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C28(H28A,H28B,H28C), C10A(H10D,H10E,H10F), C28A(H28D,
 H28E,H28F)
;