Design and Green Synthesis of Novel Benzotriazoloquinolinyl Spirooxindolopyrrolizidines: Antimycobacterial and Antiproliferative studies
POGAKU, VINAY; Vagolu, Siva Krishna; Balachandran, Chandrasekar; Krishnan, R.; Dharmarajan, Sriram; Aoki, Shin; Basavoju, Srininvas; New Journal of Chemistry 43 (2019) 17511–17520; doi:10.1039/C9NJ03802G

data_7058911
_publ_section_title
;
 Design and Green Synthesis of Novel Benzotriazoloquinolinyl
 Spirooxindolopyrrolizidines: Antimycobacterial and Antiproliferative
 studies
;
_journal_issue                   44
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17511
_journal_page_last               17520
_journal_paper_doi               10.1039/C9NJ03802G
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C36 H26 Br Cl N6 O2'
_chemical_formula_sum            'C36 H26 Br Cl N6 O2'
_chemical_formula_weight         689.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     dual
_audit_creation_date             2018-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-14 deposited with the CCDC.    2019-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.402(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7974(6)
_cell_length_b                   8.9666(3)
_cell_length_c                   21.2412(8)
_cell_measurement_reflns_used    13746
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      29.8480
_cell_measurement_theta_min      3.5970
_cell_volume                     3124.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.890
_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    -84.00  32.00   0.50   30.00    --    0.00 -82.00  60.00  232
  2  \w    -26.00  19.00   0.50   30.00    --    0.00 -37.00 150.00   90
  3  \w    -88.00 -59.00   0.50   30.00    --    0.00 -57.00-120.00   58
  4  \w    -15.00  10.00   0.50   30.00    --    0.00 -57.00-120.00   50
  5  \w    -85.00 -59.00   0.50   30.00    --    0.00 -82.00-150.00   52
  6  \w    -48.00 -22.00   0.50   30.00    --    0.00 -82.00-150.00   52
  7  \w    -27.00  -2.00   0.50   30.00    --    0.00 -57.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0415068000
_diffrn_orient_matrix_UB_12      0.0029480000
_diffrn_orient_matrix_UB_13      -0.0163634000
_diffrn_orient_matrix_UB_21      -0.0046398000
_diffrn_orient_matrix_UB_22      -0.0762727000
_diffrn_orient_matrix_UB_23      0.0072496000
_diffrn_orient_matrix_UB_31      -0.0112481000
_diffrn_orient_matrix_UB_32      0.0207188000
_diffrn_orient_matrix_UB_33      0.0291244000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32646
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.837
_diffrn_reflns_theta_min         3.354
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       Block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         8001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+2.1567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6918
_reflns_number_total             8001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj03802g2.cif
_cod_data_source_block           exp_304_p4
_cod_database_code               7058911
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C17(H17), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 N6(H6), C36(H36), C5(H5), C3(H3), C35(H35), C8(H8), C33(H33), C29(H29),
 C32(H32), C7(H7), C6(H6A), C27(H27), C26(H26), C15(H15), C12(H12), C14(H14),
 C13(H13)
;
_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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.847