Solid-phase reactive chromatography (SPRC): a sustainable method for the synthesis of benzimidazol-diphenyl-2-imino-thiazolidine-4-ols (hemiaminals) which are active against lung cancer
Bangade, V. M.; Mali, P. R.; Meshram, H. M.; RSC Advances 11 (2021) 2320–2324; doi:10.1039/D0RA09082D

data_7242057
_publ_section_title
;
 Solid-phase reactive chromatography (SPRC): a sustainable method for the
 synthesis of benzimidazol-diphenyl-2-imino-thiazolidine-4-ols
 (hemiaminals) which are active against lung cancer
;
_journal_issue                   4
_journal_name_full               'RSC Advances'
_journal_page_first              2320
_journal_page_last               2324
_journal_paper_doi               10.1039/D0RA09082D
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'Br, C23 H19 Br Cl N4 O S, H2 O, C H4 O'
_chemical_formula_sum            'C24 H25 Br2 Cl N4 O3 S'
_chemical_formula_weight         644.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4973)
;
_audit_update_record
;
2014-12-27 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                71.877(10)
_cell_angle_beta                 79.537(9)
_cell_angle_gamma                78.741(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9404(8)
_cell_length_b                   11.6089(14)
_cell_length_c                   15.7240(18)
_cell_measurement_reflns_used    3295
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7207
_cell_measurement_theta_min      2.9798
_cell_volume                     1339.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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      293(2)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details
;
  1 omega  -51.00   35.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000 -150.0000 86

  2 omega  -67.00  -41.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  125.0000 -180.0000 26

  3 omega  -66.00   32.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  150.0000 98

  4 omega  -85.00  -36.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -50.0000  -60.0000 49

  5 omega   25.00  104.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -60.0000 79

  6 omega   82.00  115.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 33

  7 omega   11.00   58.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 47

  8 omega   53.00  113.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 60

  9 omega   25.00   71.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 46

 10 omega   77.00  105.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -180.0000 28

 11 omega  -12.00   68.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -30.0000 80

 12 omega   37.00  111.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 74

 13 omega   45.00   90.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 45

 14 omega   40.00   92.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 52

 15 omega   44.00   88.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 44

 16 omega   41.00  132.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -90.0000 91

 17 omega   37.00   75.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 38

 18 omega   65.00   92.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 27

 19 omega   48.00  113.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 65

 20 omega   97.00  164.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 67

 21 omega   63.00   96.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -90.0000 33

 22 omega   50.00   94.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 44

 23 omega   38.00   64.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 26

 24 omega   45.00  176.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  -30.0000 131

 25 omega   36.00   63.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 27

 26 omega   51.00  116.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 65
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1247698000
_diffrn_orient_matrix_UB_12      -0.0441220000
_diffrn_orient_matrix_UB_13      0.0719801000
_diffrn_orient_matrix_UB_21      0.1421526000
_diffrn_orient_matrix_UB_22      0.0623332000
_diffrn_orient_matrix_UB_23      -0.0696173000
_diffrn_orient_matrix_UB_31      -0.0634719000
_diffrn_orient_matrix_UB_32      0.1187633000
_diffrn_orient_matrix_UB_33      0.0279572000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8394
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.857
_diffrn_reflns_theta_min         2.982
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.713
_refine_diff_density_min         -1.292
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1045P)^2^+2.8972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2408
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3624
_reflns_number_total             4826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra09082d2.cif
_cod_data_source_block           HMM-7-OH
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C16 H16.67 Br1.33 Cl0.67 N2.67 O2 S0.67'
_cod_original_formula_weight         429.87
_cod_original_formula_moiety
'0.67(Br), 0.67(C23 H19 Br Cl N4 O S), 0.67(H2 O), 0.67(C H4 O)'
_cod_original_formula_units_Z            3
_cod_database_code               7242057
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C24 H26 N3 S'
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.277
_reflns_odcompleteness_completeness 96.02
_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, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C14(H14), C21(H21), C22(H22), C18(H18), C2(H2A), C13(H13),
 C19(H19), C11(H11), C1(H1B), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1S(H1SA,H1SB,H1SC)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1S(H1S)
;
_shelx_res_checksum              79460
_olex2_submission_special_instructions 'No special instructions were received'