Some new morpholine-based Schiff-base complexes; Synthesis, characterization, anticancer activities and theoretical studies
Rezaeivala, Majid; Ahmadi, Musa; Captain, Burjor; Bayat, Mehdi; Saeidirad, Mahdi; Şahin-Bölükbaşı, Serap; Yıldız, Batuhan; Gable, Robert William; Inorganica Chimica Acta 513 (2020) 119935–; doi:10.1016/j.ica.2020.119935

data_1564017
_publ_section_title
;
 Some new morpholine-based Schiff-base complexes; Synthesis,
 characterization, anticancer activities and theoretical studies
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119935
_journal_paper_doi               10.1016/j.ica.2020.119935
_journal_volume                  513
_journal_year                    2020
_chemical_formula_moiety         'C22 H30 N4 Ni O2, 2(Cl O4), H2 O'
_chemical_formula_sum            'C22 H32 Cl2 N4 Ni O11'
_chemical_formula_weight         658.12
_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   mixed
_cell_angle_alpha                83.977(3)
_cell_angle_beta                 79.946(3)
_cell_angle_gamma                89.994(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8867(15)
_cell_length_b                   11.3521(19)
_cell_length_c                   14.071(2)
_cell_measurement_reflns_used    3426
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.33
_cell_volume                     1389.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.990
_diffrn_reflns_theta_min         1.478
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.955
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       needle
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         7172
_refine_ls_number_restraints     289
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0661P)^2^+0.2362P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1415
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4692
_reflns_number_total             7172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            NI_A9rwg.cif
_cod_data_source_block           ni_a9
_cod_original_cell_volume        1389.7(4)
_cod_database_code               1564017
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.911
_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 O(H,H) groups
2. Restrained distances
 Cl1-O3 = Cl1-O4 = Cl1-O5 = Cl1-O6
 1.42 with sigma of 0.001
 O3-O4 = O3-O5 = O3-O6 = O4-O5 = O4-O6 = O5-O6
 2.31859 with sigma of 0.001
 Cl1A-O3A = Cl1A-O4A = Cl1A-O5A = Cl1A-O6A
 1.42 with sigma of 0.001
 O3A-O4A = O3A-O5A = O3A-O6A = O4A-O5A = O4A-O6A = O5A-O6A
 2.31859 with sigma of 0.001
 Cl1B-O3B = Cl1B-O4B = Cl1B-O5B = Cl1B-O6B
 1.42 with sigma of 0.001
 O3B-O4B = O3B-O5B = O3B-O6B = O4B-O5B = O4B-O6B = O5B-O6B
 2.31859 with sigma of 0.001
 Cl2-O7 = Cl2-O8 = Cl2-O9 = Cl2-O10
 1.42 with sigma of 0.001
 O7-O8 = O7-O9 = O7-O10 = O8-O9 = O8-O10 = O9-O10
 2.31859 with sigma of 0.001
 Cl2A-O7A = Cl2A-O8A = Cl2A-O9A = Cl2A-O10A
 1.42 with sigma of 0.001
 O7A-O8A = O7A-O9A = O7A-O10A = O8A-O9A = O8A-O10A = O9A-O10A
 2.31859 with sigma of 0.001
 Cl2B-O7B = Cl2B-O8B = Cl2B-O9B = Cl2B-O10B
 1.42 with sigma of 0.001
 O7B-O8B = O7B-O9B = O7B-O10B = O8B-O9B = O8B-O10B = O9B-O10B
 2.31859 with sigma of 0.001
 H11A-H11B
 1.35 with sigma of 0.001
 O11-H11A = O11-H11B
 0.82 with sigma of 0.001
 O8B-C16_$2
 -3.01 with sigma of 0.001
 O10B-C7_$1
 -3.01 with sigma of 0.001
 H4-H11A
 -2.13 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
O3 \\sim O4 \\sim O5 \\sim O6 \\sim O3A \\sim O4A \\sim O5A \\sim O6A \\sim O3B
\\sim O4B \\sim O5B \\sim O6B: within 1.7A with sigma of 0.005 and sigma for
terminal atoms of 0.01
O7 \\sim O7A \\sim O7B \\sim O8 \\sim O8A \\sim O8B \\sim O9 \\sim O9A \\sim
O9B \\sim O10 \\sim O10A \\sim O10B: within 1.7A with sigma of 0.005 and sigma
for terminal atoms of 0.01
Cl1 \\sim Cl1A \\sim Cl1B: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
Cl2 \\sim Cl2A \\sim Cl2B: within 2A with sigma of 0.003 and sigma for terminal
atoms of 0.01
4. Others
 1*[Sof(Cl1)+Sof(O3)+Sof(O4)+Sof(O5)+Sof(O6)]+1*[Sof(Cl1A)+Sof(O3A)+Sof(O4A)+
 Sof(O5A)+Sof(O6A)]+1*[Sof(Cl1B)+Sof(O3B)+Sof(O4B)+Sof(O5B)+Sof(O6B)]=1 with
 esd of 0.0001
 1*[Sof(Cl2)+Sof(O7)+Sof(O8)+Sof(O9)+Sof(O10)]+1*[Sof(Cl2A)+Sof(O7A)+Sof(O8A)+
 Sof(O9A)+Sof(O10A)]+1*[Sof(Cl2B)+Sof(O7B)+Sof(O8B)+Sof(O9B)+Sof(O10B)]=1 with
 esd of 0.0001
 Sof(Cl1)=Sof(O3)=Sof(O4)=Sof(O5)=Sof(O6)=FVAR(1)
 Sof(Cl1A)=Sof(O3A)=Sof(O4A)=Sof(O5A)=Sof(O6A)=FVAR(2)
 Sof(Cl1B)=Sof(O3B)=Sof(O4B)=Sof(O5B)=Sof(O6B)=FVAR(3)
 1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=1(DFIX)=FVAR(4)
 Sof(Cl2)=Sof(O7)=Sof(O8)=Sof(O9)=Sof(O10)=FVAR(5)
 Sof(Cl2A)=Sof(O7A)=Sof(O8A)=Sof(O9A)=Sof(O10A)=FVAR(6)
 Sof(Cl2B)=Sof(O7B)=Sof(O8B)=Sof(O9B)=Sof(O10B)=FVAR(7)
5.a Ternary CH refined with riding coordinates:
 N4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C16(H16A,H16B), C17(H17A,H17B),
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4A), C5(H5), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15)
;
_shelx_res_checksum              40412
_shelx_hkl_checksum              51398