Organotin(IV) derivatives of amide-based carboxylates: Synthesis, spectroscopic characterization, single crystal studies and antimicrobial, antioxidant, cytotoxic, anti-leishmanial, hemolytic, noncancerous, anticancer activities
Ahmad, Iftikhar; Zia-ur-Rehman,; Waseem, Amir; Tariq, Muhammad; MacBeth, Cora; Bacsa, John; Venkataraman, Deepak; Rajakumar, Augustine; Ullah, Nazif; Tabassum, Saira; Inorganica Chimica Acta 505 (2020) 119433–; doi:10.1016/j.ica.2020.119433

data_1565214
_publ_section_title
;
 Organotin(IV) derivatives of amide-based carboxylates: Synthesis,
 spectroscopic characterization, single crystal studies and antimicrobial,
 antioxidant, cytotoxic, anti-leishmanial, hemolytic, noncancerous,
 anticancer activities
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119433
_journal_paper_doi               10.1016/j.ica.2020.119433
_journal_volume                  505
_journal_year                    2020
_chemical_formula_moiety         'C14 H19 N O4 Sn'
_chemical_formula_sum            'C14 H19 N O4 Sn'
_chemical_formula_weight         383.99
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 91.774(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5424(3)
_cell_length_b                   6.9070(2)
_cell_length_c                   23.3651(8)
_cell_measurement_reflns_used    9449
_cell_measurement_temperature    99.93(16)
_cell_measurement_theta_max      77.2170
_cell_measurement_theta_min      3.7420
_cell_volume                     1539.24(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.93(16)
_diffrn_detector                 HyPix
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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    -45.00  25.00   0.50    0.50    --  -47.95  38.00  90.00  140
  2  \w    -58.00 -31.00   0.50    2.00    --  -86.25 110.00 106.00   54
  3  \w    -86.00 -21.00   0.50    0.50    --  -47.95 110.00 106.00  130
  4  \w    -25.00  61.00   0.50    0.50    --   47.95 -19.00  60.00  172
  5  \w     20.00  81.00   0.50    0.50    --   47.95-110.00  11.00  122
  6  \w     60.00 109.00   0.50    2.00    --  107.75-110.00  11.00   98
  7  \w     80.00 117.00   0.50    2.00    --  107.75-125.00 -30.00   74
  8  \w     71.00 121.00   0.50    2.00    --  107.75-125.00 -90.00  100
  9  \w     69.00 108.00   0.50    2.00    --  107.75 -77.00  30.00   78
 10  \w     44.00  86.00   0.50    2.00    --  107.75 -61.00  30.00   84
 11  \w     37.00  85.00   0.50    2.00    --  107.75 -45.00  30.00   96
 12  \w     36.00  84.00   0.50    2.00    --  107.75 -45.00  90.00   96
 13  \w     53.00  80.00   0.50    2.00    --  107.75 -61.00 150.00   54
 14  \w     49.00  85.00   0.50    2.00    --  107.75 -45.00 150.00   72
 15  \w     35.00  82.00   0.50    2.00    --  107.75-125.00 150.00   94
 16  \w     86.00 121.00   0.50    2.00    --  107.75-125.00 150.00   70
 17  \w     39.00  64.00   0.50    2.00    --  107.75 -77.00  30.00   50
 18  \w     36.00  69.00   0.50    2.00    --  107.75-125.00 -30.00   66
 19  \w     45.00  85.00   0.50    2.00    --  107.75 -45.00 -90.00   80
 20  \w     95.00 130.00   0.50    2.00    --  107.75  15.00-150.00   70
 21  \w    139.00 178.00   0.50    2.00    --  107.75  15.00-150.00   78
 22  \w    149.00 174.00   0.50    2.00    --  107.75  77.00   0.00   50
 23  \w    136.00 166.00   0.50    2.00    --  107.75 125.00  30.00   60
 24  \w    134.00 171.00   0.50    2.00    --  107.75 125.00  90.00   74
 25  \w    116.00 148.00   0.50    2.00    --  107.75 110.00 106.00   64
 26  \w     92.00 123.00   0.50    2.00    --  107.75 125.00  30.00   62
 27  \w     96.00 123.00   0.50    2.00    --  107.75 125.00  90.00   54
 28  \w     85.00 140.00   0.50    2.00    --  107.75  77.00   0.00  110
 29  \w     86.00 117.00   0.50    2.00    --  107.75 -15.00-180.00   62
 30  \w     37.00  83.00   0.50    2.00    --  107.75 -95.00-180.00   92
 31  \w     33.00 102.00   0.50    2.00    --  107.75 -15.00 -90.00  138
 32  \w     33.00  79.00   0.50    2.00    --  107.75 -15.00-180.00   92
 33  \w     39.00  83.00   0.50    2.00    --  107.75 -45.00-150.00   88
 34  \w     -2.00  63.00   0.50    0.50    --   47.95 -57.00  30.00  130
 35  \w    -70.00 -16.00   0.50    2.00    --  -86.25  45.00  60.00  108
 36  \w   -106.00 -80.00   0.50    2.00    --  -86.25-110.00  11.00   52
 37  \w   -119.00 -73.00   0.50    0.50    --  -47.95-125.00  90.00   92
 38  \w   -119.00 -82.00   0.50    0.50    --  -47.95-125.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0543281000
_diffrn_orient_matrix_UB_12      0.1778386000
_diffrn_orient_matrix_UB_13      0.0336454000
_diffrn_orient_matrix_UB_21      0.0122821000
_diffrn_orient_matrix_UB_22      -0.1234346000
_diffrn_orient_matrix_UB_23      0.0549649000
_diffrn_orient_matrix_UB_31      0.1515492000
_diffrn_orient_matrix_UB_32      -0.0535359000
_diffrn_orient_matrix_UB_33      -0.0142677000
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15835
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.073
_diffrn_reflns_theta_min         3.785
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    13.321
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_correction_T_min  0.061
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.049
_refine_diff_density_max         1.728
_refine_diff_density_min         -1.150
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0708P)^2^+1.8016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2770
_reflns_number_total             2933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ICA-2020-505-119433.cif
_cod_data_source_block           i-c-11
_cod_original_cell_volume        1539.25(9)
_cod_database_code               1565214
_chemical_oxdiff_formula         'C56 H76 Sn4 N4 O16'
_diffrn_oxdiff_ac3_digest_frames
;
01c29f05e6ea2a98ae58022bf86251d622032805abb
;
_diffrn_oxdiff_ac3_digest_hkl
;
0106a50105a8571b197b50a9ceaf19adcd0b6c
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3. Rigid body (RIGU) restrains
 O1, C4, C5, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C5, C6
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C6, C7, O3, N1
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 N1, C8, C9, C10, C11, C12, C13
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C11, O4, C14
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C2, Sn1, C1, C3
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 O1, C4, O2
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 Sn1, O1
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C10(H10), C6(H6), C5(H5), C13(H13), C12(H12)
4.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;