#------------------------------------------------------------------------------
#$Date: 2023-07-06 11:42:15 +0300 (Thu, 06 Jul 2023) $
#$Revision: 285039 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/94/1569475.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1569475
loop_
_publ_author_name
'Gai, Shuangshuang'
'He, Liqin'
'He, Mingxian'
'Zhong, Xuwei'
'Jiang, Caiyun'
'Qin, Yiming'
'Jiang, Ming'
_publ_section_title
;
 Anticancer Activity and Mode of Action of Cu(II), Zn(II), and Mn(II)
 Complexes with 5-Chloro-2-N-(2-quinolylmethylene)aminophenol.
;
_journal_issue                   12
_journal_name_full               'Molecules (Basel, Switzerland)'
_journal_page_first              4876
_journal_paper_doi               10.3390/molecules28124876
_journal_volume                  28
_journal_year                    2023
_chemical_formula_moiety         'C16 H14 Cl2 Mn N2 O3, C H4 O'
_chemical_formula_sum            'C17 H18 Cl2 Mn N2 O4'
_chemical_formula_weight         440.17
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                107.037(8)
_cell_angle_beta                 100.842(9)
_cell_angle_gamma                105.105(9)
_cell_formula_units_Z            2
_cell_length_a                   7.080(4)
_cell_length_b                   11.346(6)
_cell_length_c                   13.326(7)
_cell_measurement_reflns_used    1595
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.44
_cell_measurement_theta_min      3.03
_cell_volume                     946.7(9)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11247
_diffrn_reflns_theta_full        26.59
_diffrn_reflns_theta_max         26.59
_diffrn_reflns_theta_min         1.67
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'metallic brownish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0716P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1350
_reflns_number_gt                2510
_reflns_number_total             3931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C3.cif
_cod_data_source_block           hm-ii05
_cod_database_code               1569475
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 O3(H3A), O2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
2.c Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00D)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn01 Mn 0.29495(8) 0.33121(5) 0.57220(5) 0.03483(19) Uani 1 1 d . . .
Cl1 Cl -0.07791(15) 0.30261(10) 0.50645(9) 0.0489(3) Uani 1 1 d . . .
Cl2 Cl 0.3282(2) -0.06701(13) 0.06718(9) 0.0681(4) Uani 1 1 d . . .
O1 O 0.3436(4) 0.2844(2) 0.4099(2) 0.0383(6) Uani 1 1 d . . .
O3 O 0.3425(5) 0.5369(3) 0.6059(3) 0.0487(8) Uani 1 1 d . . .
H3A H 0.4525 0.5734 0.5912 0.073 Uiso 1 1 d R . .
O2 O 0.6318(5) 0.3899(3) 0.6515(3) 0.0504(8) Uani 1 1 d . . .
H2A H 0.6880 0.3550 0.6049 0.076 Uiso 1 1 d R . .
N1 N 0.2750(4) 0.1227(3) 0.5181(2) 0.0323(7) Uani 1 1 d . . .
N2 N 0.2493(4) 0.2557(3) 0.7164(2) 0.0374(7) Uani 1 1 d . . .
C009 C 0.2934(5) 0.0703(3) 0.4132(3) 0.0334(8) Uani 1 1 d . . .
C00A C 0.3295(5) 0.1611(3) 0.3594(3) 0.0351(8) Uani 1 1 d . . .
O4 O 0.1369(6) 0.3551(4) 0.2586(3) 0.0882(12) Uani 1 1 d . . .
H4 H 0.1849 0.3394 0.3123 0.132 Uiso 1 1 calc R . .
C00C C 0.2469(5) 0.0611(4) 0.5836(3) 0.0374(9) Uani 1 1 d . . .
H00C H 0.2351 -0.0268 0.5624 0.045 Uiso 1 1 calc R . .
C00D C 0.2337(5) 0.1300(4) 0.6918(3) 0.0381(9) Uani 1 1 d . . .
C00E C 0.3421(6) 0.1164(4) 0.2528(3) 0.0430(9) Uani 1 1 d . . .
H00E H 0.3649 0.1738 0.2154 0.052 Uiso 1 1 calc R . .
C00F C 0.2393(6) 0.3226(4) 0.8183(3) 0.0408(9) Uani 1 1 d . . .
C00G C 0.2756(6) -0.0595(4) 0.3604(3) 0.0391(9) Uani 1 1 d . . .
H00G H 0.2541 -0.1180 0.3970 0.047 Uiso 1 1 calc R . .
C00H C 0.2894(6) -0.1027(4) 0.2550(3) 0.0461(10) Uani 1 1 d . . .
H00H H 0.2780 -0.1892 0.2199 0.055 Uiso 1 1 calc R . .
C00I C 0.2162(6) 0.2617(5) 0.8973(3) 0.0511(11) Uani 1 1 d . . .
C00J C 0.3210(6) -0.0126(4) 0.2027(3) 0.0443(10) Uani 1 1 d . . .
C00K C 0.2073(6) 0.0633(4) 0.7649(4) 0.0489(10) Uani 1 1 d . . .
H00K H 0.1964 -0.0245 0.7444 0.059 Uiso 1 1 calc R . .
C00L C 0.1980(7) 0.1296(5) 0.8658(4) 0.0561(12) Uani 1 1 d . . .
H00L H 0.1792 0.0864 0.9146 0.067 Uiso 1 1 calc R . .
C00M C 0.2566(7) 0.4553(4) 0.8471(4) 0.0554(11) Uani 1 1 d . . .
H00M H 0.2717 0.4967 0.7968 0.067 Uiso 1 1 calc R . .
C00N C 0.2091(7) 0.3347(6) 1.0006(4) 0.0644(13) Uani 1 1 d . . .
H00N H 0.1909 0.2951 1.0517 0.077 Uiso 1 1 calc R . .
C00O C 0.2512(8) 0.5232(5) 0.9493(4) 0.0699(14) Uani 1 1 d . . .
H00O H 0.2626 0.6110 0.9684 0.084 Uiso 1 1 calc R . .
C00P C 0.2283(8) 0.4610(6) 1.0258(4) 0.0714(15) Uani 1 1 d . . .
H00P H 0.2267 0.5089 1.0953 0.086 Uiso 1 1 calc R . .
C00Q C -0.0714(9) 0.2876(6) 0.2189(5) 0.0895(18) Uani 1 1 d . . .
H00A H -0.1341 0.3099 0.2765 0.134 Uiso 1 1 calc R . .
H00B H -0.0951 0.1952 0.1931 0.134 Uiso 1 1 calc R . .
H00D H -0.1293 0.3111 0.1596 0.134 Uiso 1 1 calc R . .
H2B H 0.702(7) 0.452(4) 0.679(4) 0.041(15) Uiso 1 1 d . . .
H3B H 0.252(8) 0.544(6) 0.583(5) 0.08(2) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn01 Cl1 95.59(8) . . ?
O1 Mn01 O2 90.69(11) . . ?
O1 Mn01 N1 73.98(10) . . ?
O1 Mn01 N2 145.92(10) . . ?
O3 Mn01 Cl1 84.59(10) . . ?
O3 Mn01 O1 97.30(11) . . ?
O3 Mn01 O2 87.13(13) . . ?
O3 Mn01 N1 170.61(12) . . ?
O3 Mn01 N2 116.35(12) . . ?
O2 Mn01 Cl1 170.18(9) . . ?
O2 Mn01 N2 86.00(11) . . ?
N1 Mn01 Cl1 99.51(8) . . ?
N1 Mn01 O2 89.46(11) . . ?
N1 Mn01 N2 72.08(11) . . ?
N2 Mn01 Cl1 92.95(8) . . ?
C00A O1 Mn01 116.2(2) . . ?
Mn01 O3 H3A 110.5 . . ?
Mn01 O3 H3B 109(5) . . ?
H3A O3 H3B 119.3 . . ?
Mn01 O2 H2A 109.7 . . ?
Mn01 O2 H2B 128(4) . . ?
H2A O2 H2B 102.8 . . ?
C009 N1 Mn01 115.7(2) . . ?
C00C N1 Mn01 118.5(3) . . ?
C00C N1 C009 125.8(3) . . ?
C00D N2 Mn01 112.8(2) . . ?
C00D N2 C00F 118.0(3) . . ?
C00F N2 Mn01 129.2(2) . . ?
N1 C009 C00A 114.1(3) . . ?
C00G C009 N1 125.6(3) . . ?
C00G C009 C00A 120.2(3) . . ?
O1 C00A C009 119.8(3) . . ?
O1 C00A C00E 121.9(3) . . ?
C00E C00A C009 118.2(3) . . ?
C00Q O4 H4 109.5 . . ?
N1 C00C H00C 120.3 . . ?
N1 C00C C00D 119.5(3) . . ?
C00D C00C H00C 120.3 . . ?
N2 C00D C00C 117.2(3) . . ?
N2 C00D C00K 123.3(4) . . ?
C00K C00D C00C 119.6(4) . . ?
C00A C00E H00E 120.0 . . ?
C00J C00E C00A 120.0(4) . . ?
C00J C00E H00E 120.0 . . ?
N2 C00F C00I 121.7(4) . . ?
N2 C00F C00M 119.4(3) . . ?
C00M C00F C00I 118.9(4) . . ?
C009 C00G H00G 119.5 . . ?
C00H C00G C009 121.1(3) . . ?
C00H C00G H00G 119.5 . . ?
C00G C00H H00H 121.1 . . ?
C00G C00H C00J 117.9(4) . . ?
C00J C00H H00H 121.0 . . ?
C00L C00I C00F 117.4(4) . . ?
C00L C00I C00N 123.1(4) . . ?
C00N C00I C00F 119.5(4) . . ?
C00E C00J Cl2 118.9(3) . . ?
C00E C00J C00H 122.6(4) . . ?
C00H C00J Cl2 118.5(3) . . ?
C00D C00K H00K 120.6 . . ?
C00L C00K C00D 118.8(4) . . ?
C00L C00K H00K 120.6 . . ?
C00I C00L H00L 119.6 . . ?
C00K C00L C00I 120.8(4) . . ?
C00K C00L H00L 119.6 . . ?
C00F C00M H00M 120.2 . . ?
C00O C00M C00F 119.7(4) . . ?
C00O C00M H00M 120.2 . . ?
C00I C00N H00N 119.9 . . ?
C00P C00N C00I 120.2(4) . . ?
C00P C00N H00N 119.9 . . ?
C00M C00O H00O 119.8 . . ?
C00M C00O C00P 120.4(5) . . ?
C00P C00O H00O 119.8 . . ?
C00N C00P C00O 121.3(5) . . ?
C00N C00P H00P 119.3 . . ?
C00O C00P H00P 119.3 . . ?
O4 C00Q H00A 109.5 . . ?
O4 C00Q H00B 109.5 . . ?
O4 C00Q H00D 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
H00A C00Q H00D 109.5 . . ?
H00B C00Q H00D 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn01 Cl1 2.5214(18) . ?
Mn01 O1 2.187(3) . ?
Mn01 O3 2.163(3) . ?
Mn01 O2 2.249(4) . ?
Mn01 N1 2.219(3) . ?
Mn01 N2 2.364(3) . ?
Cl2 C00J 1.744(4) . ?
O1 C00A 1.330(4) . ?
O3 H3A 0.8682 . ?
O3 H3B 0.69(5) . ?
O2 H2A 0.8549 . ?
O2 H2B 0.69(4) . ?
N1 C009 1.394(4) . ?
N1 C00C 1.282(4) . ?
N2 C00D 1.335(5) . ?
N2 C00F 1.373(5) . ?
C009 C00A 1.417(5) . ?
C009 C00G 1.394(5) . ?
C00A C00E 1.391(5) . ?
O4 H4 0.8200 . ?
O4 C00Q 1.386(7) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.458(5) . ?
C00D C00K 1.409(5) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.373(5) . ?
C00F C00I 1.430(6) . ?
C00F C00M 1.407(6) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.377(5) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.392(6) . ?
C00I C00L 1.396(6) . ?
C00I C00N 1.401(6) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.359(6) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00O 1.368(6) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.336(7) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.411(7) . ?
C00P H00P 0.9300 . ?
C00Q H00A 0.9600 . ?
C00Q H00B 0.9600 . ?
C00Q H00D 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn01 O1 C00A C009 -2.5(4) . . . . ?
Mn01 O1 C00A C00E 175.1(3) . . . . ?
Mn01 N1 C009 C00A 2.2(4) . . . . ?
Mn01 N1 C009 C00G -176.6(3) . . . . ?
Mn01 N1 C00C C00D -1.4(4) . . . . ?
Mn01 N2 C00D C00C 0.1(4) . . . . ?
Mn01 N2 C00D C00K 179.5(3) . . . . ?
Mn01 N2 C00F C00I -178.3(3) . . . . ?
Mn01 N2 C00F C00M 0.3(5) . . . . ?
Cl1 Mn01 O1 C00A -95.6(2) . . . . ?
Cl1 Mn01 N1 C009 90.5(2) . . . . ?
Cl1 Mn01 N1 C00C -89.0(3) . . . . ?
Cl1 Mn01 N2 C00D 98.5(2) . . . . ?
Cl1 Mn01 N2 C00F -82.2(3) . . . . ?
O1 Mn01 N1 C009 -2.6(2) . . . . ?
O1 Mn01 N1 C00C 177.9(3) . . . . ?
O1 Mn01 N2 C00D -6.0(3) . . . . ?
O1 Mn01 N2 C00F 173.4(3) . . . . ?
O1 C00A C00E C00J -178.1(3) . . . . ?
O3 Mn01 O1 C00A 179.1(2) . . . . ?
O3 Mn01 N1 C009 -24.8(9) . . . . ?
O3 Mn01 N1 C00C 155.7(7) . . . . ?
O3 Mn01 N2 C00D -176.1(2) . . . . ?
O3 Mn01 N2 C00F 3.3(3) . . . . ?
O2 Mn01 O1 C00A 91.9(2) . . . . ?
O2 Mn01 N1 C009 -93.5(2) . . . . ?
O2 Mn01 N1 C00C 87.0(3) . . . . ?
O2 Mn01 N2 C00D -91.3(2) . . . . ?
O2 Mn01 N2 C00F 88.1(3) . . . . ?
N1 Mn01 O1 C00A 2.7(2) . . . . ?
N1 Mn01 N2 C00D -0.5(2) . . . . ?
N1 Mn01 N2 C00F 178.8(3) . . . . ?
N1 C009 C00A O1 0.2(5) . . . . ?
N1 C009 C00A C00E -177.6(3) . . . . ?
N1 C009 C00G C00H 177.7(3) . . . . ?
N1 C00C C00D N2 0.8(5) . . . . ?
N1 C00C C00D C00K -178.6(3) . . . . ?
N2 Mn01 O1 C00A 8.1(3) . . . . ?
N2 Mn01 N1 C009 -179.4(3) . . . . ?
N2 Mn01 N1 C00C 1.0(3) . . . . ?
N2 C00D C00K C00L -0.3(6) . . . . ?
N2 C00F C00I C00L -1.9(6) . . . . ?
N2 C00F C00I C00N 179.3(4) . . . . ?
N2 C00F C00M C00O -178.6(4) . . . . ?
C009 N1 C00C C00D 179.1(3) . . . . ?
C009 C00A C00E C00J -0.4(6) . . . . ?
C009 C00G C00H C00J -0.2(6) . . . . ?
C00A C009 C00G C00H -1.0(6) . . . . ?
C00A C00E C00J Cl2 177.7(3) . . . . ?
C00A C00E C00J C00H -0.8(6) . . . . ?
C00C N1 C009 C00A -178.3(3) . . . . ?
C00C N1 C009 C00G 2.9(6) . . . . ?
C00C C00D C00K C00L 179.1(4) . . . . ?
C00D N2 C00F C00I 1.0(5) . . . . ?
C00D N2 C00F C00M 179.6(3) . . . . ?
C00D C00K C00L C00I -0.6(6) . . . . ?
C00F N2 C00D C00C -179.3(3) . . . . ?
C00F N2 C00D C00K 0.1(5) . . . . ?
C00F C00I C00L C00K 1.7(6) . . . . ?
C00F C00I C00N C00P -1.5(7) . . . . ?
C00F C00M C00O C00P 0.0(7) . . . . ?
C00G C009 C00A O1 179.1(3) . . . . ?
C00G C009 C00A C00E 1.3(5) . . . . ?
C00G C00H C00J Cl2 -177.4(3) . . . . ?
C00G C00H C00J C00E 1.2(6) . . . . ?
C00I C00F C00M C00O 0.0(6) . . . . ?
C00I C00N C00P C00O 1.6(8) . . . . ?
C00L C00I C00N C00P 179.8(4) . . . . ?
C00M C00F C00I C00L 179.5(4) . . . . ?
C00M C00F C00I C00N 0.7(6) . . . . ?
C00M C00O C00P C00N -0.8(8) . . . . ?
C00N C00I C00L C00K -179.6(4) . . . . ?
