Mn(III), Zn(II) and Pt(II) macroacyclic complexes: Synthesis, X-ray structures, anticancer and antioxidant activities
Keypour, Hassan; Ansari, Neda; Mahmoudabadi, Masoumeh; Karamian, Roya; Moazzami Farida, Seyed Hamed; Eslami Moghadam, Mahboube; William Gable, Robert; Inorganica Chimica Acta 509 (2020) 119705–; doi:10.1016/j.ica.2020.119705

data_1564471
_publ_section_title
;
 Mn(III), Zn(II) and Pt(II) macroacyclic complexes: Synthesis, X-ray
 structures, anticancer and antioxidant activities
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119705
_journal_paper_doi               10.1016/j.ica.2020.119705
_journal_volume                  509
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H30 Mn N4 O2, Cl O4, 0.58(C H4 O)'
_chemical_formula_sum            'C32.58 H32.31 Cl Mn N4 O6.58'
_chemical_formula_weight         675.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 92.7800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.80100(10)
_cell_length_b                   17.1118(2)
_cell_length_c                   10.43020(10)
_cell_measurement_reflns_used    13559
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.3210
_cell_measurement_theta_min      4.2440
_cell_volume                     1568.95(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -35.00  18.00   0.50    0.05    --  -48.17  38.00 -90.00  106
  2  \w    -14.00  26.00   0.50    0.05    --  -48.17  19.00 -30.00   80
  3  \w    -28.00  23.00   0.50    0.05    --  -48.17  19.00 -60.00  102
  4  \w    -28.00  26.00   0.50    0.05    --  -48.17  19.00-120.00  108
  5  \w    -62.00  24.00   0.50    0.05    --  -48.17  57.00   0.00  172
  6  \w      1.00  73.00   0.50    0.05    --   48.17 -99.00 150.00  144
  7  \w     36.00  92.00   0.50    0.05    --   48.17-125.00  90.00  112
  8  \w     50.00 108.00   0.50    0.16    --  107.75-125.00  30.00  116
  9  \w     79.00 111.00   0.50    0.16    --  107.75-125.00  90.00   64
 10  \w     81.00 108.00   0.50    0.16    --  107.75-125.00 150.00   54
 11  \w     66.00  94.00   0.50    0.16    --  107.75 -94.00 120.00   56
 12  \w     53.00  79.00   0.50    0.16    --  107.75-125.00 150.00   52
 13  \w     62.00 109.00   0.50    0.16    --  107.75-112.00 166.52   94
 14  \w     39.00  90.00   0.50    0.16    --  107.75 -77.00  60.00  102
 15  \w     69.00 105.00   0.50    0.16    --  107.75 -98.00   3.39   72
 16  \w     79.00 106.00   0.50    0.16    --  107.75 -98.00 -75.13   54
 17  \w     81.00 106.00   0.50    0.16    --  107.75 -94.00-150.00   50
 18  \w     75.00 105.00   0.50    0.16    --  107.75 -94.00-180.00   60
 19  \w     71.00 101.00   0.50    0.16    --  107.75 -77.00 -90.00   60
 20  \w     49.00 100.00   0.50    0.16    --  107.75 -77.00-120.00  102
 21  \w     42.00  67.00   0.50    0.16    --  107.75 -61.00 -90.00   50
 22  \w     37.00  63.00   0.50    0.16    --  107.75 -94.00-150.00   52
 23  \w     36.00  97.00   0.50    0.16    --  107.75 -77.00-150.00  122
 24  \w     41.00  76.00   0.50    0.16    --  107.75-125.00 -90.00   70
 25  \w     38.00  63.00   0.50    0.16    --  107.75 -94.00 -60.00   50
 26  \w     36.00  99.00   0.50    0.16    --  107.75 -94.00  30.00  126
 27  \w     45.00  71.00   0.50    0.16    --  107.75 -61.00  60.00   52
 28  \w     37.00  62.00   0.50    0.16    --  107.75 -61.00  90.00   50
 29  \w     36.00  61.00   0.50    0.16    --  107.75 -61.00  30.00   50
 30  \w     97.00 166.00   0.50    0.16    --  107.75  15.00  90.00  138
 31  \w     99.00 174.00   0.50    0.16    --  107.75  45.00  30.00  150
 32  \w    147.00 178.00   0.50    0.16    --  107.75  61.00 -30.00   62
 33  \w    146.00 172.00   0.50    0.16    --  107.75  77.00 -60.00   52
 34  \w    140.00 165.00   0.50    0.16    --  107.75 125.00 -60.00   50
 35  \w    102.00 175.00   0.50    0.16    --  107.75  30.00 -90.00  146
 36  \w    136.00 166.00   0.50    0.16    --  107.75  45.00-180.00   60
 37  \w     97.00 136.00   0.50    0.16    --  107.75 125.00 -60.00   78
 38  \w     96.00 126.00   0.50    0.16    --  107.75  77.00 -60.00   60
 39  \w     98.00 143.00   0.50    0.16    --  107.75  61.00 -30.00   90
 40  \w     99.00 177.00   0.50    0.16    --  107.75  30.00 -60.00  156
 41  \w     98.00 140.00   0.50    0.16    --  107.75  61.00 120.00   84
 42  \w    103.00 137.00   0.50    0.16    --  107.75  45.00 150.00   68
 43  \w    137.00 163.00   0.50    0.16    --  107.75 125.00 150.00   52
 44  \w    103.00 133.00   0.50    0.16    --  107.75 125.00 150.00   60
 45  \w     41.00  66.00   0.50    0.16    --  107.75 -94.00-180.00   50
 46  \w   -130.00-104.00   0.50    0.16    --  -86.25 -15.00 150.00   52
 47  \w    -97.00 -65.00   0.50    0.16    --  -86.25 -77.00  90.00   64
;
_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      -0.0363086000
_diffrn_orient_matrix_UB_12      0.0874398000
_diffrn_orient_matrix_UB_13      -0.0189284000
_diffrn_orient_matrix_UB_21      -0.0432268000
_diffrn_orient_matrix_UB_22      -0.0151947000
_diffrn_orient_matrix_UB_23      -0.1426996000
_diffrn_orient_matrix_UB_31      -0.1659076000
_diffrn_orient_matrix_UB_32      -0.0151616000
_diffrn_orient_matrix_UB_33      0.0337971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21941
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.951
_diffrn_reflns_theta_min         4.244
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.342
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53a (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            'dark brown'
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       needle
_exptl_crystal_F_000             701
_exptl_crystal_recrystallization_method
'vapour diffusion of methanol into acetonitrile'
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.361(5)
_refine_ls_extinction_coef       0.0025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         6329
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0448P)^2^+0.8429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                6218
_reflns_number_total             6329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rwg2019_11Gau.cif
_cod_data_source_block           rwg2019_11gau
_cod_database_code               1564471
_chemical_oxdiff_formula         'C33 H34 Cl Mn N4 O7'
_chemical_oxdiff_usercomment     MAH1
_diffrn_oxdiff_digest_frames
;
012184296f8e680fb98d878395547adf6f038548ba2
;
_diffrn_oxdiff_digest_hkl
;
01278af6826911c24b01aac30a474da49d1db7
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.639(5)
 0.361(5)
2. 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, All O(H) groups
3. Others
 Sof(O7)=Sof(H7A)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C29(H29), C30(H30),
  C31(H31), C32(H32)
4.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_shelx_res_checksum              65539
_shelx_hkl_checksum              2138
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_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 1.569
_oxdiff_exptl_absorpt_empirical_full_min 0.797