Design, synthesis and molecular modelling of novel methyl[4-oxo-2-(aroylimino)-3-(substituted phenyl)thiazolidin-5-ylidene]acetates as potent and selective aldose reductase inhibitors
Ali, Sher; Saeed, Aamer; Abbas, Naeem; Shahid, Mohammad; Bolte, Michael; Iqbal, Jamshed; MedChemComm 3 (2012) 1428–; doi:10.1039/c2md20228j

data_7112582
_publ_section_title
;
 Design, synthesis and molecular modelling of novel
 methyl[4-oxo-2-(aroylimino)-3-(substituted
 phenyl)thiazolidin-5-ylidene]acetates as potent and selective aldose
 reductase inhibitors
;
_journal_issue                   11
_journal_name_full               MedChemComm
_journal_page_first              1428
_journal_paper_doi               10.1039/c2md20228j
_journal_volume                  3
_journal_year                    2012
_chemical_formula_moiety         'C19 H11 Br Cl2 N2 O4 S'
_chemical_formula_sum            'C19 H11 Br Cl2 N2 O4 S'
_chemical_formula_weight         514.17
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.708(6)
_cell_angle_beta                 73.497(6)
_cell_angle_gamma                69.745(6)
_cell_formula_units_Z            2
_cell_length_a                   9.2497(7)
_cell_length_b                   10.8904(9)
_cell_length_c                   11.0733(9)
_cell_measurement_reflns_used    12513
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      3.5
_cell_volume                     1003.34(15)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_sigmaI/netI    0.0668
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_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12503
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.448
_exptl_absorpt_correction_T_max  0.6274
_exptl_absorpt_correction_T_min  0.5685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.096
_refine_diff_density_min         -1.165
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_refine_ls_extinction_coef       0.013(5)
_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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1266P)^2^+0.2504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.1928
_reflns_number_gt                3029
_reflns_number_total             3787
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2md20228j.txt
_cod_data_source_block           sa56
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1003.34(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7112582