#------------------------------------------------------------------------------
#$Date: 2019-11-24 07:18:05 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/78/4087898.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_4087898
loop_
_publ_author_name
'Al-Afyouni, Malik H.'
'Krishnan, V. Mahesh'
'Arman, Hadi D.'
'Tonzetich, Zachary J.'
_publ_section_title
;
 Synthesis and Reactivity of Manganese(II) Complexes Containing
 N-Heterocyclic Carbene Ligands
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5088
_journal_paper_doi               10.1021/acs.organomet.5b00684
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C54 H58 Cl2 Mn2 N4'
_chemical_formula_sum            'C54 H58 Cl2 Mn2 N4'
_chemical_formula_weight         943.82
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.149(9)
_cell_angle_beta                 98.265(13)
_cell_angle_gamma                93.340(15)
_cell_formula_units_Z            1
_cell_length_a                   9.895(2)
_cell_length_b                   11.700(2)
_cell_length_c                   12.259(2)
_cell_measurement_reflns_used    4448
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      3.0
_cell_volume                     1248.9(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8814
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.397
_refine_diff_density_rms         '0.064 ===END'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                4587
_reflns_number_total             5664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00684_si_002.cif
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4087898
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
Mn1 Mn 0.57548(3) 0.64260(3) 0.01462(3) 0.02256(11) Uani 1 1 d .
Cl1 Cl 0.66421(5) 0.45608(5) 0.02745(5) 0.02711(13) Uani 1 1 d .
N2 N 0.75332(18) 0.70762(17) -0.15200(15) 0.0247(4) Uani 1 1 d .
N1 N 0.56443(18) 0.59621(17) -0.26982(16) 0.0252(4) Uani 1 1 d .
C1 C 0.6326(2) 0.64670(19) -0.15082(18) 0.0220(4) Uani 1 1 d .
C14 C 0.8627(2) 0.7745(2) -0.04534(19) 0.0250(4) Uani 1 1 d .
C19 C 0.8624(2) 0.9048(2) 0.0309(2) 0.0275(5) Uani 1 1 d .
C23 C 0.6217(2) 0.8158(2) 0.18245(18) 0.0277(5) Uani 1 1 d .
C4 C 0.4292(2) 0.5209(2) -0.31608(18) 0.0254(4) Uani 1 1 d .
C24 C 0.7576(2) 0.8512(2) 0.2554(2) 0.0301(5) Uani 1 1 d .
H24A H 0.8238 0.7973 0.2277 0.036 Uiso 1 1 calc R
C15 C 0.9647(2) 0.7057(2) -0.0241(2) 0.0280(5) Uani 1 1 d .
C9 C 0.4205(2) 0.3878(2) -0.36041(18) 0.0291(5) Uani 1 1 d .
C8 C 0.2896(3) 0.3170(2) -0.4076(2) 0.0348(5) Uani 1 1 d .
H8A H 0.2808 0.2282 -0.4380 0.042 Uiso 1 1 calc R
C20 C 0.9613(2) 0.5652(2) -0.1111(2) 0.0351(5) Uani 1 1 d .
H20A H 1.0384 0.5332 -0.0821 0.053 Uiso 1 1 calc R
H20B H 0.9663 0.5553 -0.1924 0.053 Uiso 1 1 calc R
H20C H 0.8772 0.5178 -0.1142 0.053 Uiso 1 1 calc R
C17 C 1.0690(2) 0.8995(2) 0.1623(2) 0.0332(5) Uani 1 1 d .
C25 C 0.7943(2) 0.9643(2) 0.3674(2) 0.0336(5) Uani 1 1 d .
H25A H 0.8842 0.9859 0.4120 0.040 Uiso 1 1 calc R
C18 C 0.9680(2) 0.9655(2) 0.1344(2) 0.0311(5) Uani 1 1 d .
H18A H 0.9710 1.0526 0.1863 0.037 Uiso 1 1 calc R
C16 C 1.0673(2) 0.7703(2) 0.0814(2) 0.0331(5) Uani 1 1 d .
H16A H 1.1360 0.7262 0.0980 0.040 Uiso 1 1 calc R
C5 C 0.3139(2) 0.5834(2) -0.3180(2) 0.0328(5) Uani 1 1 d .
C3 C 0.7601(3) 0.6947(2) -0.2690(2) 0.0353(6) Uani 1 1 d .
H3A H 0.8326 0.7281 -0.2916 0.042 Uiso 1 1 calc R
C22 C 0.7492(2) 0.9766(2) 0.0077(2) 0.0333(5) Uani 1 1 d .
H22A H 0.6854 0.9203 -0.0668 0.050 Uiso 1 1 calc R
H22B H 0.7884 1.0485 -0.0011 0.050 Uiso 1 1 calc R
H22C H 0.7016 1.0070 0.0761 0.050 Uiso 1 1 calc R
C2 C 0.6418(3) 0.6246(2) -0.3429(2) 0.0362(6) Uani 1 1 d .
H2A H 0.6164 0.5997 -0.4271 0.043 Uiso 1 1 calc R
C7 C 0.1711(3) 0.3755(3) -0.4105(2) 0.0382(6) Uani 1 1 d .
C6 C 0.1854(2) 0.5074(3) -0.3658(2) 0.0390(6) Uani 1 1 d .
H6A H 0.1067 0.5468 -0.3676 0.047 Uiso 1 1 calc R
C28 C 0.5305(2) 0.8983(2) 0.2298(2) 0.0371(6) Uani 1 1 d .
H28A H 0.4410 0.8789 0.1849 0.044 Uiso 1 1 calc R
C26 C 0.6952(3) 1.0434(2) 0.4108(2) 0.0371(6) Uani 1 1 d .
H26A H 0.7175 1.1180 0.4856 0.045 Uiso 1 1 calc R
C27 C 0.5628(3) 1.0106(2) 0.3419(2) 0.0422(6) Uani 1 1 d .
H27A H 0.4956 1.0631 0.3702 0.051 Uiso 1 1 calc R
C13 C 0.5472(3) 0.3243(2) -0.3555(2) 0.0387(6) Uani 1 1 d .
H13A H 0.5211 0.2332 -0.3893 0.058 Uiso 1 1 calc R
H13B H 0.5939 0.3578 -0.2712 0.058 Uiso 1 1 calc R
H13C H 0.6074 0.3412 -0.4030 0.058 Uiso 1 1 calc R
C21 C 1.1765(3) 0.9671(3) 0.2792(2) 0.0471(7) Uani 1 1 d .
H21A H 1.2375 0.9081 0.2845 0.071 Uiso 1 1 calc R
H21B H 1.1321 0.9980 0.3496 0.071 Uiso 1 1 calc R
H21C H 1.2284 1.0383 0.2778 0.071 Uiso 1 1 calc R
C11 C 0.3282(3) 0.7269(3) -0.2665(3) 0.0518(7) Uani 1 1 d .
H11A H 0.4240 0.7619 -0.2380 0.078 Uiso 1 1 calc R
H11B H 0.2801 0.7616 -0.1987 0.078 Uiso 1 1 calc R
H11C H 0.2897 0.7491 -0.3300 0.078 Uiso 1 1 calc R
C12 C 0.0299(3) 0.2959(3) -0.4583(3) 0.0571(8) Uani 1 1 d .
H12A H 0.0397 0.2069 -0.4856 0.086 Uiso 1 1 calc R
H12B H -0.0169 0.3072 -0.5264 0.086 Uiso 1 1 calc R
H12C H -0.0227 0.3234 -0.3933 0.086 Uiso 1 1 calc R
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'
Mn Mn 0.3368 0.7283 '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'
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
C23 Mn1 C1 117.42(7) . .
C23 Mn1 Cl1 111.79(6) . 2_665
C1 Mn1 Cl1 111.45(6) . 2_665
C23 Mn1 Cl1 114.66(7) . .
C1 Mn1 Cl1 106.84(6) . .
Cl1 Mn1 Cl1 91.74(2) 2_665 .
Mn1 Cl1 Mn1 88.26(2) 2_665 .
C1 N2 C3 111.70(17) . .
C1 N2 C14 124.21(16) . .
C3 N2 C14 124.06(17) . .
C1 N1 C2 111.38(17) . .
C1 N1 C4 124.78(17) . .
C2 N1 C4 123.83(17) . .
N1 C1 N2 103.57(16) . .
N1 C1 Mn1 131.85(14) . .
N2 C1 Mn1 124.57(14) . .
C15 C14 C19 123.0(2) . .
C15 C14 N2 118.25(19) . .
C19 C14 N2 118.80(19) . .
C14 C19 C18 117.1(2) . .
C14 C19 C22 122.0(2) . .
C18 C19 C22 120.7(2) . .
C28 C23 C24 115.4(2) . .
C28 C23 Mn1 125.06(18) . .
C24 C23 Mn1 119.52(17) . .
C5 C4 C9 122.9(2) . .
C5 C4 N1 118.76(19) . .
C9 C4 N1 118.3(2) . .
C25 C24 C23 122.2(2) . .
C25 C24 H24A 118.9 . .
C23 C24 H24A 118.9 . .
C14 C15 C16 117.7(2) . .
C14 C15 C20 120.69(19) . .
C16 C15 C20 121.6(2) . .
C8 C9 C4 117.3(2) . .
C8 C9 C13 121.5(2) . .
C4 C9 C13 121.3(2) . .
C9 C8 C7 121.9(2) . .
C9 C8 H8A 119.1 . .
C7 C8 H8A 119.1 . .
C15 C20 H20A 109.5 . .
C15 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C15 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C16 C17 C18 118.7(2) . .
C16 C17 C21 121.2(2) . .
C18 C17 C21 120.1(2) . .
C26 C25 C24 119.2(2) . .
C26 C25 H25A 120.4 . .
C24 C25 H25A 120.4 . .
C17 C18 C19 122.0(2) . .
C17 C18 H18A 119.0 . .
C19 C18 H18A 119.0 . .
C17 C16 C15 121.5(2) . .
C17 C16 H16A 119.3 . .
C15 C16 H16A 119.3 . .
C4 C5 C6 117.2(2) . .
C4 C5 C11 120.9(2) . .
C6 C5 C11 121.8(2) . .
C2 C3 N2 106.50(19) . .
C2 C3 H3A 126.8 . .
N2 C3 H3A 126.8 . .
C19 C22 H22A 109.5 . .
C19 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C19 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C3 C2 N1 106.84(19) . .
C3 C2 H2A 126.6 . .
N1 C2 H2A 126.6 . .
C6 C7 C8 118.6(2) . .
C6 C7 C12 121.0(3) . .
C8 C7 C12 120.4(2) . .
C7 C6 C5 122.2(2) . .
C7 C6 H6A 118.9 . .
C5 C6 H6A 118.9 . .
C23 C28 C27 124.0(2) . .
C23 C28 H28A 118.0 . .
C27 C28 H28A 118.0 . .
C27 C26 C25 119.5(2) . .
C27 C26 H26A 120.2 . .
C25 C26 H26A 120.2 . .
C26 C27 C28 119.7(2) . .
C26 C27 H27A 120.2 . .
C28 C27 H27A 120.2 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C17 C21 H21A 109.5 . .
C17 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C17 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C5 C11 H11A 109.5 . .
C5 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C5 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C7 C12 H12A 109.5 . .
C7 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C7 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 C23 2.121(2) .
Mn1 C1 2.202(2) .
Mn1 Cl1 2.4553(8) 2_665
Mn1 Cl1 2.4585(7) .
Cl1 Mn1 2.4553(8) 2_665
N2 C1 1.360(3) .
N2 C3 1.386(3) .
N2 C14 1.444(3) .
N1 C1 1.358(3) .
N1 C2 1.389(3) .
N1 C4 1.446(3) .
C14 C15 1.392(3) .
C14 C19 1.394(3) .
C19 C18 1.395(3) .
C19 C22 1.507(3) .
C23 C28 1.357(3) .
C23 C24 1.429(3) .
C4 C5 1.394(3) .
C4 C9 1.397(3) .
C24 C25 1.402(3) .
C24 H24A 0.9300 .
C15 C16 1.394(3) .
C15 C20 1.510(3) .
C9 C8 1.392(3) .
C9 C13 1.501(3) .
C8 C7 1.396(4) .
C8 H8A 0.9300 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C17 C16 1.392(3) .
C17 C18 1.392(3) .
C17 C21 1.508(3) .
C25 C26 1.388(3) .
C25 H25A 0.9300 .
C18 H18A 0.9300 .
C16 H16A 0.9300 .
C5 C6 1.395(3) .
C5 C11 1.500(3) .
C3 C2 1.339(3) .
C3 H3A 0.9300 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C2 H2A 0.9300 .
C7 C6 1.382(4) .
C7 C12 1.514(3) .
C6 H6A 0.9300 .
C28 C27 1.397(3) .
C28 H28A 0.9300 .
C26 C27 1.383(4) .
C26 H26A 0.9300 .
C27 H27A 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
