Synthesis, biological evaluation and molecular docking studies of novel 1-(4,5-dihydro-1H-pyrazol-1-yl)ethanone-containing 1-methylindol derivatives as potential tubulin assembling inhibitors
Yang, Meng-Ru; Qin, Ya-Juan; Chen, Chen; Zhang, Ya-Liang; Li, Bo-Yan; Liu, Tian-Bao; Gong, Hai-Bin; Wang, Bao-Zhong; Zhu, Hai-Liang; RSC Adv. 6 (2016) 30412–; doi:10.1039/C5RA28141E

data_7224704
_publ_section_title
;
 Synthesis, biological evaluation and molecular docking studies of novel
 1-(4,5-dihydro-1H-pyrazol-1-yl)ethanone-containing 1-methylindol
 derivatives as potential tubulin assembling inhibitors
;
_journal_issue                   36
_journal_name_full               'RSC Adv.'
_journal_page_first              30412
_journal_paper_doi               10.1039/C5RA28141E
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C21 H20 Br N3 O2'
_chemical_formula_sum            'C21 H20 Br N3 O2'
_chemical_formula_weight         426.31
_chemical_melting_point          453.6(5)
_chemical_name_systematic        6o
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-12-31 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.896(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5763(14)
_cell_length_b                   8.0259(7)
_cell_length_c                   15.6946(13)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.57
_cell_volume                     1963.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16844
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    2.114
_exptl_absorpt_correction_T_max  0.9116
_exptl_absorpt_correction_T_min  0.8587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol/dichloromethane'
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+2.1703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                2428
_reflns_number_total             3457
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra28141e1.cif
_cod_data_source_block           zyl-149
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '180-181 \%C' was changed to
'453.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7224704