Antiproliferative activity of bicyclic benzimidazole nucleosides: synthesis, DNA-binding and cell cycle analysis.
Sontakke, Vyankat A.; Lawande, Pravin P.; Kate, Anup N.; Khan, Ayesha; Joshi, Rakesh; Kumbhar, Anupa A.; Shinde, Vaishali S.; Organic & biomolecular chemistry 14 (2016) 4136–4145; doi:10.1039/c6ob00527f

data_7155062
_publ_section_title
;
 Antiproliferative activity of bicyclic benzimidazole nucleosides:
 synthesis, DNA-binding and cell cycle analysis.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4136
_journal_page_last               4145
_journal_paper_doi               10.1039/c6ob00527f
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C14 H13 Cl N2 O3'
_chemical_formula_weight         292.71
_chemical_melting_point          386.1(10)
_chemical_name_common            NA
_chemical_name_systematic        'Bicyclic benzimidazole nucleoside'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-03-08 deposited with the CCDC.
2016-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7554(4)
_cell_length_b                   18.6455(5)
_cell_length_c                   5.38910(10)
_cell_measurement_temperature    273(2)
_cell_volume                     1382.18(6)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.956
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            12954
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.978
_diffrn_reflns_theta_min         1.840
_exptl_absorpt_coefficient_mu    0.285
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Flack x determined using 1405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         4311
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.848
_refine_ls_shift/su_mean         0.039
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0968P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.832
_reflns_number_gt                3811
_reflns_number_total             4311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00527f2.cif
_cod_data_source_block           BNU2P21212
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '112-114 oC' was changed to
'386.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155061--7155062.cif.
;
_cod_database_code               7155062
_shelxl_version_number           2014/6
_shelx_res_checksum              87938