Influence of the diversified structural variations at the imine functionality of 4-bromophenylacetic acid derived hydrazones on alkaline phosphatase inhibition: synthesis and molecular modelling studies
Khan, Imtiaz; Ibrar, Aliya; Ejaz, Syeda Abida; Khan, Shafi Ullah; Shah, Syed Jawad Ali; Hameed, Shahid; Simpson, Jim; Lecka, Joanna; Sévigny, Jean; Iqbal, Jamshed; RSC Advances 5 (2015) 90806–; doi:10.1039/C5RA14836G

data_7235946
_publ_section_title
;
 Influence of the diversified structural variations at the imine
 functionality of 4-bromophenylacetic acid derived hydrazones on alkaline
 phosphatase inhibition: synthesis and molecular modelling studies
;
_journal_issue                   110
_journal_name_full               'RSC Advances'
_journal_page_first              90806
_journal_paper_doi               10.1039/C5RA14836G
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C21 H17 Br N2 O'
_chemical_formula_sum            'C21 H17 Br N2 O'
_chemical_formula_weight         393.27
_chemical_name_systematic
;
E)-N'-(biphenyl-4-ylmethylene)-2-(4-bromophenyl)acetohydrazide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-05-19 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.621(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   20.4423(11)
_cell_length_b                   5.5758(3)
_cell_length_c                   7.6350(7)
_cell_measurement_reflns_used    4457
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6700
_cell_measurement_theta_min      6.5320
_cell_volume                     860.42(10)
_computing_cell_refinement       'CrysAlisPro, Agilent (2013)'
_computing_data_collection       'CrysAlisPro, Agilent (2013)'
_computing_data_reduction        'CrysAlisPro, Agilent (2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2008), enCIFer (Allen <i>et al.</i>, 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 1997)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2015b) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.1725
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7517
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.127
_diffrn_reflns_theta_min         4.375
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent (2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'triangular block'
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_refine_diff_density_max         3.267
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.193
_refine_ls_abs_structure_details
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0858
_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^)+(0.1359P)^2^+6.9116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2443
_refine_ls_wR_factor_ref         0.2495
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.763
_reflns_Friedel_fraction_max     0.727
_reflns_number_gt                2814
_reflns_number_total             3007
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra14836g2.cif
_cod_data_source_block           isb13_Compound_II
_cod_original_cell_volume        860.43(10)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7235946
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.555
_shelx_estimated_absorpt_t_max   0.825
_shelx_res_checksum              84840