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_1565212
_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         'C24 H33 F6 N O3 Sn'
_chemical_formula_sum            'C24 H33 F6 N O3 Sn'
_chemical_formula_weight         616.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                94.4327(11)
_cell_angle_beta                 94.1063(12)
_cell_angle_gamma                104.0709(12)
_cell_formula_units_Z            4
_cell_length_a                   9.66459(14)
_cell_length_b                   14.1481(2)
_cell_length_c                   21.1011(3)
_cell_measurement_reflns_used    35604
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.7910
_cell_measurement_theta_min      1.5170
_cell_volume                     2778.11(7)
_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_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -69.00 -28.00   0.50    4.00    --  -17.92 120.00  19.10   82
  2  \w    -41.00  56.00   0.50    4.00    --  -17.92  57.00   0.00  194
  3  \w     -5.00  86.00   0.50    4.00    --   17.76  38.00  30.00  182
  4  \w     -4.00  62.00   0.50    4.00    --   17.76-107.00  35.00  132
  5  \w     39.00  96.00   0.50    4.00    --   17.76 178.00 150.00  114
  6  \w    -59.00  41.00   0.50    4.00    --   17.76 -38.00-120.00  200
  7  \w     -5.00  92.00   0.50    4.00    --   17.76  57.00-180.00  194
  8  \w    -26.00  22.00   0.50    4.00    --  -17.92 -99.00-120.00   96
  9  \w    -56.00  41.00   0.50    4.00    --   17.76 -57.00-180.00  194
 10  \w    -92.00   5.00   0.50    4.00    --  -17.92 -57.00-150.00  194
 11  \w    -26.00  22.00   0.50    4.00    --  -17.92 -99.00  90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684250000
_diffrn_orient_matrix_UB_12      0.0100952000
_diffrn_orient_matrix_UB_13      -0.0030460000
_diffrn_orient_matrix_UB_21      -0.0090837000
_diffrn_orient_matrix_UB_22      -0.0183204000
_diffrn_orient_matrix_UB_23      -0.0326819000
_diffrn_orient_matrix_UB_31      -0.0317911000
_diffrn_orient_matrix_UB_32      -0.0475351000
_diffrn_orient_matrix_UB_33      0.0083278000
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            47756
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.491
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.402
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.473
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.156
_refine_diff_density_max         1.733
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         10167
_refine_ls_number_restraints     419
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0935P)^2^+8.0399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1661
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8945
_reflns_number_total             10167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ICA-2020-505-119433.cif
_cod_data_source_block           i-c-20_i
_cod_original_cell_volume        2778.12(7)
_cod_database_code               1565212
_chemical_oxdiff_formula         'C80  H114  F24  N14  O16  Sn4  '
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.744
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14_14-C15_14
 1.52 with sigma of 0.005
 C13_14-C14_14
 1.52 with sigma of 0.005
 C15_14-C14_14
 1.55 with sigma of 0.005
 C13_9-C14_9
 1.52 with sigma of 0.002
 C13_9-C12_9
 1.52 with sigma of 0.01
 C15_1-C14_1
 1.55 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(F2_11) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C11_11) \\sim Ueq, Uanis(F3_11) \\sim Ueq, Uanis(F1_11) \\sim Ueq: with
sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(F2_10) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(F3_10) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(F1_10) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C11_12) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C11_11) = Uanis(C11_10)
4. Rigid body (RIGU) restrains
 F1_6, F2_6, F3_6, C11_6
 F1_11, F2_11, F3_11, C11_11
 F1_5, F2_5, F3_5, C11_5
 F1_7, F2_7, F3_7, C11_7
 F1_10, F2_10, F3_10, C11_10
 F1_12, F2_12, F3_12, C11_12
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 C12_13, C13_13, C14_13, C15_13
 C12_14, C13_14, C14_14, C15_14
 C12_8, C13_8, C14_8, C15_8
 C12_4, C13_4, C14_4, C15_4
 C12_9, C13_9, C14_9, C15_9
 C12_1, C13_1, C14_1, C15_1
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.001
 Sn1, C12_1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Same fragment restrains
{C12_14, C13_14, C14_14, C15_14}
{C12_8, C13_8, C14_8, C15_8}
{C12_4, C13_4, C14_4, C15_4}
{C12_9, C13_9, C14_9, C15_9}
{C12_1, C13_1, C14_1, C15_1}
as
{C12_13, C13_13, C14_13, C15_13} sigma for 1-2: 0.001 1-3: 0.002
{F1_11, F2_11, F3_11, C11_11}
{F1_5, F2_5, F3_5, C11_5}
{F1_7, F2_7, F3_7, C11_7}
{F1_10, F2_10, F3_10, C11_10}
{F1_12, F2_12, F3_12, C11_12}
as
{F1_6, F2_6, F3_6, C11_6} sigma for 1-2: 0.001 1-3: 0.002
6. Others
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(C11)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(C11)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(C11)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(C11)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C12(H12A,H12B), C13(H13A,
 H13B), C14(H14A,H14B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C12(H12A,H12B), C13(H13A,H13B),
  C14(H14A,H14B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C10(H10), N1(H1), C2B(H2B), C3B(H3B),
 C6B(H6B), C8B(H8B), C10B(H10B), N1B(H1B)
7.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15(H15A,H15B,H15C), C15(H15A,H15B,H15C), C15(H15A,H15B,
 H15C), C15(H15A,H15B,H15C), C15(H15A,H15B,H15C)
;