Structural and biological evaluation of halogen derivatives of 1,9-pyrazoloanthrones towards the design of a specific potent inhibitor of c-Jun-N-terminal kinase (JNK)
Ganduri, Ramesh; Singh, Vikas; Biswas, Ansuman; Karothu, Durga Prasad; Sekar, Kanagaraj; Balaji, Kithiganahalli N.; Guru Row, Tayur N.; New Journal of Chemistry 42 (2018) 10651–; doi:10.1039/C8NJ00852C

data_7057437
_publ_section_title
;
 Structural and biological evaluation of halogen derivatives of
 1,9-pyrazoloanthrones towards the design of a specific potent inhibitor
 of c-Jun-N-terminal kinase (JNK)
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10651
_journal_paper_doi               10.1039/C8NJ00852C
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C16 H10 Cl2 N2 O'
_chemical_formula_sum            'C16 H10 Cl2 N2 O'
_chemical_formula_weight         317.16
_chemical_name_systematic        1-chloroethylene-5-chloro-1,9-pyrazoloanthrone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-05 deposited with the CCDC.
2018-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.283(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7039(5)
_cell_length_b                   14.5890(10)
_cell_length_c                   13.9378(9)
_cell_measurement_reflns_used    2668
_cell_measurement_temperature    100.08(2)
_cell_measurement_theta_max      25.5690
_cell_measurement_theta_min      3.1580
_cell_volume                     1354.97(16)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.08(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -89.00  12.00   1.00   16.00    --  -18.48 -77.00 120.00  101
  2  \w     -8.00  93.00   1.00   16.00    --   22.54  77.00  60.00  101
  3  \w      1.00  91.00   1.00   16.00    --   22.54  57.00   0.00   90
  4  \w    -48.00  53.00   1.00   16.00    --   22.54 -77.00 -60.00  101
  5  \w    -48.00  53.00   1.00   16.00    --   22.54 -77.00-150.00  101
  6  \w    -44.00  54.00   1.00   16.00    --  -18.48  37.00  90.00   98
  7  \w      1.00  79.00   1.00   16.00    --   22.54  57.00 -90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0500017000
_diffrn_orient_matrix_UB_12      0.0221867000
_diffrn_orient_matrix_UB_13      0.0358356000
_diffrn_orient_matrix_UB_21      -0.0404397000
_diffrn_orient_matrix_UB_22      0.0324919000
_diffrn_orient_matrix_UB_23      -0.0346696000
_diffrn_orient_matrix_UB_31      -0.0848187000
_diffrn_orient_matrix_UB_32      -0.0285612000
_diffrn_orient_matrix_UB_33      -0.0116323000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1024
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18436
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.478
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeoH-THF'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0964
_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^)+(0.0603P)^2^+8.7860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2226
_refine_ls_wR_factor_ref         0.2391
_reflns_number_gt                2314
_reflns_number_total             3099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8nj00852c2.cif
_cod_data_source_block           r2-3-red
_cod_depositor_comments          'Adding full bibliography for 7057437.cif.'
_cod_database_code               7057437
_chemical_oxdiff_formula         'C H N O Cl'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10), C4(H4), C2(H2), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.873