#------------------------------------------------------------------------------
#$Date: 2021-10-29 05:31:07 +0300 (Fri, 29 Oct 2021) $
#$Revision: 270153 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/38/7243800.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_7243800
loop_
_publ_author_name
'Oulmidi, Afaf'
'Radi, Smaail'
'Idir, Abderrazak'
'Zyad, Abdelmajid'
'Kabach, Imad'
'Nhiri, Mohamed'
'Robeyns, Koen'
'Rotaru, Aurelian'
'Garcia, Yann'
_publ_section_title
;
 Synthesis and cytotoxicity against tumor cells of pincer N-heterocyclic
 ligands and their transition metal complexes
;
_journal_issue                   55
_journal_name_full               'RSC Advances'
_journal_page_first              34742
_journal_page_last               34753
_journal_paper_doi               10.1039/D1RA05918A
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C19 H21 Cl2 Mn N5 O4'
_chemical_formula_sum            'C19 H21 Cl2 Mn N5 O4'
_chemical_formula_weight         509.25
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-03-27 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   30.3293(6)
_cell_length_b                   30.3293(6)
_cell_length_c                   13.6082(4)
_cell_measurement_reflns_used    14013
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.6690
_cell_measurement_theta_min      2.6570
_cell_volume                     10840.7(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, ΔΦ 1.5° '
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0087
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30303
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.690
_diffrn_reflns_theta_min         2.686
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             4698
_exptl_crystal_recrystallization_method
'diffusion of ether in nitromethane solution'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.032
_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     178
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0313
_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/[σ²(Fo²)+(0.0389P)²+10.0671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2119
_reflns_number_total             2279
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra05918a2.cif
_cod_data_source_block           yg_b1m4
_cod_original_cell_volume        10840.7(5)
_cod_database_code               7243800
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.6667 0.55542(2) 0.5833 0.05260(14) Uani 1 2 d S T P . .
Cl2 Cl 0.70326(2) 0.54352(2) 0.72456(4) 0.07465(18) Uani 1 1 d . . . . .
N3 N 0.58858(6) 0.54346(6) 0.63336(11) 0.0569(4) Uani 1 1 d . . . . .
N4 N 0.58071(5) 0.58296(6) 0.61389(11) 0.0558(4) Uani 1 1 d . . . . .
C5 C 0.52954(7) 0.56713(7) 0.60551(13) 0.0570(4) Uani 1 1 d . . . . .
C6 C 0.50500(7) 0.51598(8) 0.62112(13) 0.0600(5) Uani 1 1 d . . . . .
H6 H 0.4700 0.4939 0.6206 0.072 Uiso 1 1 calc R U . . .
C7 C 0.54235(7) 0.50295(7) 0.63804(13) 0.0568(4) Uani 1 1 d . . . . .
C8 C 0.6204(5) 0.6305(3) 0.6085(12) 0.058(3) Uani 0.5 1 d G . P A -3
N9 N 0.6621(7) 0.6278(3) 0.5883(15) 0.047(2) Uani 0.5 1 d G . P A -3
C10 C 0.6206(4) 0.6757(5) 0.6137(13) 0.078(3) Uani 0.5 1 d G . P A -3
H10 H 0.5911 0.6766 0.6280 0.093 Uiso 0.5 1 calc R U P A -3
C11 C 0.6657(6) 0.7195(3) 0.5972(18) 0.093(4) Uani 0.5 1 d G . P A -3
H11 H 0.6670 0.7507 0.6010 0.112 Uiso 0.5 1 calc R U P A -3
C8B C 0.7058(5) 0.6713(5) 0.5739(11) 0.0486(17) Uani 0.5 1 d G . P A -3
C10B C 0.7089(4) 0.7180(3) 0.5750(13) 0.089(4) Uani 0.5 1 d G . P A -3
H10B H 0.7393 0.7476 0.5612 0.106 Uiso 0.5 1 calc R U P A -3
C12 C 0.50793(8) 0.60048(9) 0.58277(17) 0.0732(6) Uani 1 1 d . . . . .
H12A H 0.4722 0.5798 0.5689 0.110 Uiso 1 1 calc R U . . .
H12B H 0.5250 0.6212 0.5266 0.110 Uiso 1 1 calc R U . . .
H12C H 0.5126 0.6220 0.6382 0.110 Uiso 1 1 calc R U . . .
C13 C 0.53416(8) 0.45179(8) 0.65874(14) 0.0665(5) Uani 1 1 d . . . . .
O14 O 0.49290(6) 0.41466(6) 0.66008(15) 0.0974(6) Uani 1 1 d . . . . .
O15 O 0.57680(6) 0.45177(6) 0.67628(14) 0.0877(5) Uani 1 1 d D . . . .
C16 C 0.5729(4) 0.4023(3) 0.6930(12) 0.138(7) Uani 0.608(16) 1 d D . P B 1
H16A H 0.5436 0.3822 0.7347 0.165 Uiso 0.608(16) 1 calc R U P B 1
H16B H 0.5666 0.3848 0.6304 0.165 Uiso 0.608(16) 1 calc R U P B 1
C17 C 0.6138(3) 0.4042(3) 0.7342(13) 0.179(7) Uani 0.608(16) 1 d D . P B 1
H17A H 0.6432 0.4246 0.6944 0.268 Uiso 0.608(16) 1 calc R U P B 1
H17B H 0.6086 0.3703 0.7394 0.268 Uiso 0.608(16) 1 calc R U P B 1
H17C H 0.6189 0.4189 0.7986 0.268 Uiso 0.608(16) 1 calc R U P B 1
C16B C 0.5729(8) 0.4036(5) 0.7053(15) 0.133(10) Uani 0.392(16) 1 d D . P B 2
H16C H 0.5892 0.4071 0.7685 0.159 Uiso 0.392(16) 1 calc R U P B 2
H16D H 0.5374 0.3773 0.7107 0.159 Uiso 0.392(16) 1 calc R U P B 2
C17B C 0.5962(11) 0.3910(6) 0.6361(15) 0.220(12) Uani 0.392(16) 1 d D . P B 2
H17D H 0.6278 0.4205 0.6183 0.329 Uiso 0.392(16) 1 calc R U P B 2
H17E H 0.5747 0.3782 0.5792 0.329 Uiso 0.392(16) 1 calc R U P B 2
H17F H 0.6027 0.3652 0.6612 0.329 Uiso 0.392(16) 1 calc R U P B 2
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'
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'
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'
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
N9 Mn1 N3 72.6(5) . 18_655 ?
N9 Mn1 N3 65.8(5) . . ?
N3 Mn1 N3 138.37(8) 18_655 . ?
N9 Mn1 Cl2 112.9(5) . . ?
N3 Mn1 Cl2 90.94(4) 18_655 . ?
N3 Mn1 Cl2 105.20(4) . . ?
N9 Mn1 Cl2 113.2(5) . 18_655 ?
N3 Mn1 Cl2 105.19(4) 18_655 18_655 ?
N3 Mn1 Cl2 90.95(4) . 18_655 ?
Cl2 Mn1 Cl2 133.83(4) . 18_655 ?
C7 N3 N4 104.83(15) . . ?
C7 N3 Mn1 133.26(13) . . ?
N4 N3 Mn1 114.95(11) . . ?
C8 N4 N3 119.9(6) . . ?
C8 N4 C5 128.2(6) . . ?
N3 N4 C5 111.82(15) . . ?
C6 C5 N4 105.22(16) . . ?
C6 C5 C12 129.21(17) . . ?
N4 C5 C12 125.57(18) . . ?
C5 C6 C7 106.89(16) . . ?
C5 C6 H6 126.6 . . ?
C7 C6 H6 126.6 . . ?
N3 C7 C6 111.24(18) . . ?
N3 C7 C13 121.98(18) . . ?
C6 C7 C13 126.78(18) . . ?
N9 C8 N4 108.3(11) . . ?
N9 C8 C10 122.7 . . ?
N4 C8 C10 128.7(11) . . ?
C8 N9 C8B 118.1 . . ?
C8 N9 Mn1 125.6(9) . . ?
C8B N9 Mn1 116.2(9) . . ?
C11 C10 C8 117.8 . . ?
C11 C10 H10 121.1 . . ?
C8 C10 H10 121.1 . . ?
C10 C11 C10B 120.9 . . ?
C10 C11 H11 119.6 . . ?
C10B C11 H11 119.6 . . ?
N9 C8B C10B 122.7 . . ?
C11 C10B C8B 117.7 . . ?
C11 C10B H10B 121.1 . . ?
C8B C10B H10B 121.1 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O14 C13 O15 124.3(2) . . ?
O14 C13 C7 122.9(2) . . ?
O15 C13 C7 112.81(17) . . ?
C13 O15 C16B 117.5(9) . . ?
C13 O15 C16 116.9(5) . . ?
C17 C16 O15 115.1(8) . . ?
C17 C16 H16A 108.5 . . ?
O15 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
O15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C17B C16B O15 107.7(10) . . ?
C17B C16B H16C 110.2 . . ?
O15 C16B H16C 110.2 . . ?
C17B C16B H16D 110.2 . . ?
O15 C16B H16D 110.2 . . ?
H16C C16B H16D 108.5 . . ?
C16B C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C16B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 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
Mn1 N9 2.268(2) . ?
Mn1 N3 2.3120(15) 18_655 ?
Mn1 N3 2.3120(15) . ?
Mn1 Cl2 2.3359(5) . ?
Mn1 Cl2 2.3359(5) 18_655 ?
N3 C7 1.326(2) . ?
N3 N4 1.359(2) . ?
N4 C8 1.340(9) . ?
N4 C5 1.381(2) . ?
C5 C6 1.360(3) . ?
C5 C12 1.487(3) . ?
C6 C7 1.393(3) . ?
C6 H6 0.9300 . ?
C7 C13 1.471(3) . ?
C8 N9 1.3374 . ?
C8 C10 1.3705 . ?
N9 C8B 1.3375 . ?
C10 C11 1.3672 . ?
C10 H10 0.9300 . ?
C11 C10B 1.3672 . ?
C11 H11 0.9300 . ?
C8B C10B 1.3706 . ?
C10B H10B 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O14 1.194(2) . ?
C13 O15 1.315(3) . ?
O15 C16B 1.462(8) . ?
O15 C16 1.462(5) . ?
C16 C17 1.336(13) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16B C17B 1.342(15) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 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
C7 N3 N4 C8 177.2(8) . . . . ?
Mn1 N3 N4 C8 -28.0(8) . . . . ?
C7 N3 N4 C5 -0.53(19) . . . . ?
Mn1 N3 N4 C5 154.31(12) . . . . ?
C8 N4 C5 C6 -177.1(9) . . . . ?
N3 N4 C5 C6 0.4(2) . . . . ?
C8 N4 C5 C12 3.7(9) . . . . ?
N3 N4 C5 C12 -178.83(18) . . . . ?
N4 C5 C6 C7 -0.2(2) . . . . ?
C12 C5 C6 C7 179.07(19) . . . . ?
N4 N3 C7 C6 0.4(2) . . . . ?
Mn1 N3 C7 C6 -147.61(14) . . . . ?
N4 N3 C7 C13 -179.60(16) . . . . ?
Mn1 N3 C7 C13 32.4(3) . . . . ?
C5 C6 C7 N3 -0.2(2) . . . . ?
C5 C6 C7 C13 179.85(17) . . . . ?
N3 N4 C8 N9 22.7(6) . . . . ?
C5 N4 C8 N9 -160.0(6) . . . . ?
N3 N4 C8 C10 -162.5(10) . . . . ?
C5 N4 C8 C10 14.8(17) . . . . ?
N4 C8 N9 C8B 176.1(11) . . . . ?
C10 C8 N9 C8B 1.0 . . . . ?
N4 C8 N9 Mn1 -7.2(6) . . . . ?
C10 C8 N9 Mn1 177.7(14) . . . . ?
N9 C8 C10 C11 0.1 . . . . ?
N4 C8 C10 C11 -174.0(13) . . . . ?
C8 C10 C11 C10B 0.8 . . . . ?
C8 N9 C8B C10B -2.9 . . . . ?
Mn1 N9 C8B C10B -179.9(13) . . . . ?
C10 C11 C10B C8B -2.5 . . . . ?
N9 C8B C10B C11 3.7 . . . . ?
N3 C7 C13 O14 -177.5(2) . . . . ?
C6 C7 C13 O14 2.5(3) . . . . ?
N3 C7 C13 O15 3.1(3) . . . . ?
C6 C7 C13 O15 -176.89(18) . . . . ?
O14 C13 O15 C16B -4.0(10) . . . . ?
C7 C13 O15 C16B 175.4(9) . . . . ?
O14 C13 O15 C16 3.6(8) . . . . ?
C7 C13 O15 C16 -177.1(8) . . . . ?
C13 O15 C16 C17 -163.9(13) . . . . ?
C13 O15 C16B C17B 117(2) . . . . ?
