Synthesis, study of antileishmanial and antitrypanosomal activity of imidazo pyridine fused triazole analogues
Nandikolla, Adinarayana; Srinivasarao, Singireddi; Karan Kumar, Banoth; Murugesan, Sankaranarayanan; Aggarwal, Himanshu; Major, Louise L.; Smith, Terry K.; Chandra Sekhar, Kondapalli Venkata Gowri; RSC Advances 10 (2020) 38328–38343; doi:10.1039/D0RA07881F

data_7241418
_publ_section_title
;
 Synthesis, study of antileishmanial and antitrypanosomal activity of
 imidazo pyridine fused triazole analogues
;
_journal_issue                   63
_journal_name_full               'RSC Advances'
_journal_page_first              38328
_journal_page_last               38343
_journal_paper_doi               10.1039/D0RA07881F
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C22 H21 Br Cl N7 O, C H2 Cl2'
_chemical_formula_sum            'C23 H23 Br Cl3 N7 O'
_chemical_formula_weight         599.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_audit_creation_date             2020-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-16 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2953(7)
_cell_length_b                   13.8502(5)
_cell_length_c                   20.9305(7)
_cell_measurement_reflns_used    13270
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.8750
_cell_measurement_theta_min      3.3640
_cell_volume                     5013.8(3)
_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  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.9246
_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     58.00  83.00   0.50   35.00    --    0.00  57.00 -60.00   50
  2  \w     22.00  48.00   0.50   35.00    --    0.00  37.00-150.00   52
  3  \w    -23.00  23.00   0.50   35.00    --    0.00  19.00 -60.00   92
  4  \w    -22.00  52.00   0.50   35.00    --    0.00  57.00   0.00  148
  5  \w    -10.00  30.00   0.50   35.00    --    0.00  57.00 -60.00   80
;
_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      -0.0275097000
_diffrn_orient_matrix_UB_12      0.0373703000
_diffrn_orient_matrix_UB_13      -0.0044318000
_diffrn_orient_matrix_UB_21      -0.0302800000
_diffrn_orient_matrix_UB_22      -0.0328525000
_diffrn_orient_matrix_UB_23      0.0070771000
_diffrn_orient_matrix_UB_31      0.0027688000
_diffrn_orient_matrix_UB_32      0.0120924000
_diffrn_orient_matrix_UB_33      0.0328571000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37545
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         29.82
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.992
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80214
_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            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5889
_exptl_crystal_description       block
_exptl_crystal_F_000             2434.0196
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.1920
_refine_diff_density_min         -0.6027
_refine_diff_density_rms         0.0913
_refine_ls_d_res_high            0.7146
_refine_ls_d_res_low             6.1456
_refine_ls_goodness_of_fit_ref   1.0393
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6649
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.0392
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+4.0659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                5454
_reflns_number_total             6649
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0ra07881f2.cif
_cod_data_source_block           KVG_223-FUR-19A
_cod_database_code               7241418
_reflns_odcompleteness_completeness 99.56
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl3B-C23B = Cl2B-C23B
 1.72 with sigma of 0.02
3. Others
 Fixed Sof: C23A(0.85) H23a(0.85) H23b(0.85) C23B(0.15) H23c(0.15) H23d(0.15)
 Cl2B(0.15) Cl2A(0.85) Cl3A(0.85) Cl3B(0.15)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C10(H10a,H10b), C9(H9a,H9b), C11(H11a,H11b), C12(H12a,H12b),
 C23A(H23a,H23b), C23B(H23c,H23d)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C3(H3), C20(H20), C5(H5), C6(H6), C19(H19), C22(H22)
4.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c)
;
_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 1.164
_oxdiff_exptl_absorpt_empirical_full_min 0.917