#------------------------------------------------------------------------------
#$Date: 2019-11-24 07:18:05 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/78/4087897.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_4087897
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         'C66 H82 Cl2 Mn2 N4'
_chemical_formula_sum            'C66 H82 Cl2 Mn2 N4'
_chemical_formula_weight         1112.14
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.875(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.016(9)
_cell_length_b                   12.006(7)
_cell_length_c                   17.858(10)
_cell_measurement_temperature    98(2)
_cell_volume                     3097(3)
_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_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.1140
_diffrn_reflns_av_sigmaI/netI    0.1004
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11738
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_T_max  0.9098
_exptl_absorpt_correction_T_min  0.8823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.828
_refine_diff_density_rms         '0.081 ===END'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0641
_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)+(0.0200P)²+6.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                4450
_reflns_number_total             5441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00684_si_002.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4087897
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.50963(4) 0.03350(5) 0.91025(3) 0.02658(17) Uani 1 1 d .
Cl1 Cl 0.55992(6) 0.12490(8) 1.03807(5) 0.0314(2) Uani 1 1 d .
N2 N 0.66674(19) 0.0458(2) 0.82091(16) 0.0244(6) Uani 1 1 d .
N1 N 0.6902(2) -0.1074(2) 0.88523(16) 0.0251(6) Uani 1 1 d .
C16 C 0.6318(2) 0.1546(3) 0.7915(2) 0.0270(8) Uani 1 1 d .
C4 C 0.6924(2) -0.1945(3) 0.9417(2) 0.0269(8) Uani 1 1 d .
C1 C 0.6344(2) -0.0154(3) 0.87259(19) 0.0243(8) Uani 1 1 d .
C21 C 0.6544(2) 0.2478(3) 0.8409(2) 0.0275(8) Uani 1 1 d .
C28 C 0.4064(2) 0.1237(3) 0.8269(2) 0.0300(8) Uani 1 1 d .
C17 C 0.5758(2) 0.1617(3) 0.7134(2) 0.0291(8) Uani 1 1 d .
C9 C 0.6297(3) -0.2843(3) 0.9224(2) 0.0323(9) Uani 1 1 d .
C3 C 0.7409(2) -0.0073(3) 0.8025(2) 0.0289(8) Uani 1 1 d .
H3A H 0.7747 0.0194 0.7683 0.035 Uiso 1 1 calc R
C25 C 0.7212(3) 0.2378(3) 0.9237(2) 0.0316(9) Uani 1 1 d .
H25A H 0.7075 0.1655 0.9461 0.038 Uiso 1 1 calc R
C18 C 0.5394(3) 0.2670(3) 0.6881(2) 0.0328(9) Uani 1 1 d .
H18A H 0.5004 0.2747 0.6366 0.039 Uiso 1 1 calc R
C5 C 0.7622(3) -0.1878(4) 1.0138(2) 0.0344(9) Uani 1 1 d .
C20 C 0.6172(3) 0.3505(3) 0.8114(2) 0.0334(9) Uani 1 1 d .
H20A H 0.6319 0.4151 0.8431 0.040 Uiso 1 1 calc R
C19 C 0.5582(3) 0.3598(3) 0.7353(2) 0.0330(9) Uani 1 1 d .
H19A H 0.5316 0.4297 0.7165 0.040 Uiso 1 1 calc R
C13 C 0.5558(3) -0.2867(4) 0.8433(2) 0.0351(9) Uani 1 1 d .
H13A H 0.5310 -0.2094 0.8319 0.042 Uiso 1 1 calc R
C27 C 0.7097(3) 0.3296(4) 0.9787(2) 0.0388(10) Uani 1 1 d .
H27A H 0.6453 0.3315 0.9811 0.058 Uiso 1 1 calc R
H27B H 0.7257 0.4014 0.9598 0.058 Uiso 1 1 calc R
H27C H 0.7506 0.3153 1.0308 0.058 Uiso 1 1 calc R
C2 C 0.7551(2) -0.1033(3) 0.8425(2) 0.0305(8) Uani 1 1 d .
H2A H 0.8006 -0.1580 0.8418 0.037 Uiso 1 1 calc R
C22 C 0.5584(3) 0.0616(4) 0.6588(2) 0.0341(9) Uani 1 1 d .
H22A H 0.5771 -0.0071 0.6909 0.041 Uiso 1 1 calc R
C29 C 0.3382(3) 0.0698(4) 0.7679(2) 0.0361(9) Uani 1 1 d .
H29A H 0.3372 -0.0093 0.7662 0.043 Uiso 1 1 calc R
C33 C 0.4024(3) 0.2401(4) 0.8262(2) 0.0341(9) Uani 1 1 d .
H33A H 0.4464 0.2796 0.8656 0.041 Uiso 1 1 calc R
C32 C 0.3369(3) 0.3018(4) 0.7705(2) 0.0399(10) Uani 1 1 d .
H32A H 0.3374 0.3809 0.7722 0.048 Uiso 1 1 calc R
C6 C 0.7679(3) -0.2753(4) 1.0652(2) 0.0428(10) Uani 1 1 d .
H6A H 0.8136 -0.2731 1.1140 0.051 Uiso 1 1 calc R
C8 C 0.6394(3) -0.3692(4) 0.9764(3) 0.0433(10) Uani 1 1 d .
H8A H 0.5983 -0.4309 0.9652 0.052 Uiso 1 1 calc R
C30 C 0.2714(3) 0.1297(4) 0.7112(2) 0.0421(11) Uani 1 1 d .
H30A H 0.2265 0.0907 0.6722 0.051 Uiso 1 1 calc R
C10 C 0.8272(3) -0.0866(4) 1.0343(2) 0.0390(10) Uani 1 1 d .
H10A H 0.8101 -0.0328 0.9899 0.047 Uiso 1 1 calc R
C26 C 0.8231(3) 0.2327(4) 0.9190(3) 0.0446(11) Uani 1 1 d .
H26A H 0.8649 0.2259 0.9716 0.067 Uiso 1 1 calc R
H26B H 0.8376 0.3008 0.8946 0.067 Uiso 1 1 calc R
H26C H 0.8309 0.1680 0.8879 0.067 Uiso 1 1 calc R
C14 C 0.5978(3) -0.3211(4) 0.7779(2) 0.0432(10) Uani 1 1 d .
H14A H 0.6498 -0.2717 0.7778 0.065 Uiso 1 1 calc R
H14B H 0.5507 -0.3155 0.7278 0.065 Uiso 1 1 calc R
H14C H 0.6200 -0.3981 0.7862 0.065 Uiso 1 1 calc R
C31 C 0.2707(3) 0.2452(4) 0.7122(2) 0.0409(10) Uani 1 1 d .
H31A H 0.2261 0.2855 0.6738 0.049 Uiso 1 1 calc R
C7 C 0.7090(3) -0.3657(4) 1.0477(3) 0.0517(12) Uani 1 1 d .
H7A H 0.7154 -0.4255 1.0836 0.062 Uiso 1 1 calc R
C24 C 0.6183(3) 0.0702(4) 0.6018(2) 0.0474(11) Uani 1 1 d .
H24A H 0.6835 0.0778 0.6311 0.071 Uiso 1 1 calc R
H24B H 0.5992 0.1355 0.5683 0.071 Uiso 1 1 calc R
H24C H 0.6103 0.0029 0.5696 0.071 Uiso 1 1 calc R
C23 C 0.4548(3) 0.0496(4) 0.6125(3) 0.0507(12) Uani 1 1 d .
H23A H 0.4167 0.0442 0.6490 0.076 Uiso 1 1 calc R
H23B H 0.4467 -0.0177 0.5803 0.076 Uiso 1 1 calc R
H23C H 0.4357 0.1149 0.5790 0.076 Uiso 1 1 calc R
C12 C 0.9289(3) -0.1229(5) 1.0452(3) 0.0564(13) Uani 1 1 d .
H12A H 0.9695 -0.0577 1.0580 0.085 Uiso 1 1 calc R
H12B H 0.9351 -0.1568 0.9970 0.085 Uiso 1 1 calc R
H12C H 0.9465 -0.1773 1.0877 0.085 Uiso 1 1 calc R
C11 C 0.8162(3) -0.0279(5) 1.1072(3) 0.0569(14) Uani 1 1 d .
H11A H 0.8583 0.0361 1.1191 0.085 Uiso 1 1 calc R
H11B H 0.8312 -0.0800 1.1511 0.085 Uiso 1 1 calc R
H11C H 0.7522 -0.0022 1.0981 0.085 Uiso 1 1 calc R
C15 C 0.4736(3) -0.3636(4) 0.8439(3) 0.0507(12) Uani 1 1 d .
H15A H 0.4473 -0.3413 0.8862 0.076 Uiso 1 1 calc R
H15B H 0.4952 -0.4408 0.8519 0.076 Uiso 1 1 calc R
H15C H 0.4261 -0.3575 0.7940 0.076 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'
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_3
C28 Mn1 C1 115.67(13) .
C28 Mn1 Cl1 113.73(11) .
C1 Mn1 Cl1 109.08(9) .
C28 Mn1 Cl1 110.62(11) 3_657
C1 Mn1 Cl1 112.67(10) 3_657
Cl1 Mn1 Cl1 92.91(5) 3_657
Mn1 Cl1 Mn1 87.09(5) 3_657
C1 N2 C3 111.5(3) .
C1 N2 C16 124.6(3) .
C3 N2 C16 123.9(3) .
C1 N1 C2 111.7(3) .
C1 N1 C4 126.5(3) .
C2 N1 C4 121.4(3) .
C21 C16 C17 123.0(3) .
C21 C16 N2 119.1(3) .
C17 C16 N2 117.8(3) .
C9 C4 C5 122.8(4) .
C9 C4 N1 119.7(3) .
C5 C4 N1 117.4(3) .
N1 C1 N2 103.3(3) .
N1 C1 Mn1 133.5(3) .
N2 C1 Mn1 122.9(2) .
C20 C21 C16 117.5(3) .
C20 C21 C25 121.1(3) .
C16 C21 C25 121.3(3) .
C33 C28 C29 115.5(3) .
C33 C28 Mn1 122.4(3) .
C29 C28 Mn1 122.1(3) .
C18 C17 C16 116.3(4) .
C18 C17 C22 121.5(3) .
C16 C17 C22 122.2(4) .
C8 C9 C4 117.2(4) .
C8 C9 C13 122.5(4) .
C4 C9 C13 120.3(3) .
C2 C3 N2 106.7(3) .
C2 C3 H3A 126.7 .
N2 C3 H3A 126.7 .
C27 C25 C21 113.8(3) .
C27 C25 C26 110.6(3) .
C21 C25 C26 110.0(3) .
C27 C25 H25A 107.4 .
C21 C25 H25A 107.4 .
C26 C25 H25A 107.4 .
C19 C18 C17 122.4(3) .
C19 C18 H18A 118.8 .
C17 C18 H18A 118.8 .
C6 C5 C4 117.0(4) .
C6 C5 C10 121.5(4) .
C4 C5 C10 121.5(4) .
C21 C20 C19 121.0(4) .
C21 C20 H20A 119.5 .
C19 C20 H20A 119.5 .
C18 C19 C20 119.7(4) .
C18 C19 H19A 120.2 .
C20 C19 H19A 120.2 .
C14 C13 C9 111.2(3) .
C14 C13 C15 110.0(3) .
C9 C13 C15 112.5(4) .
C14 C13 H13A 107.7 .
C9 C13 H13A 107.7 .
C15 C13 H13A 107.7 .
C25 C27 H27A 109.5 .
C25 C27 H27B 109.5 .
H27A C27 H27B 109.5 .
C25 C27 H27C 109.5 .
H27A C27 H27C 109.5 .
H27B C27 H27C 109.5 .
C3 C2 N1 106.8(3) .
C3 C2 H2A 126.6 .
N1 C2 H2A 126.6 .
C17 C22 C24 110.0(3) .
C17 C22 C23 112.6(3) .
C24 C22 C23 109.6(3) .
C17 C22 H22A 108.2 .
C24 C22 H22A 108.2 .
C23 C22 H22A 108.2 .
C28 C29 C30 122.1(4) .
C28 C29 H29A 119.0 .
C30 C29 H29A 119.0 .
C28 C33 C32 123.6(4) .
C28 C33 H33A 118.2 .
C32 C33 H33A 118.2 .
C31 C32 C33 119.2(4) .
C31 C32 H32A 120.4 .
C33 C32 H32A 120.4 .
C7 C6 C5 121.8(4) .
C7 C6 H6A 119.1 .
C5 C6 H6A 119.1 .
C9 C8 C7 121.2(4) .
C9 C8 H8A 119.4 .
C7 C8 H8A 119.4 .
C31 C30 C29 120.4(4) .
C31 C30 H30A 119.8 .
C29 C30 H30A 119.8 .
C11 C10 C5 110.9(4) .
C11 C10 C12 110.8(4) .
C5 C10 C12 110.3(4) .
C11 C10 H10A 108.2 .
C5 C10 H10A 108.2 .
C12 C10 H10A 108.2 .
C25 C26 H26A 109.5 .
C25 C26 H26B 109.5 .
H26A C26 H26B 109.5 .
C25 C26 H26C 109.5 .
H26A C26 H26C 109.5 .
H26B C26 H26C 109.5 .
C13 C14 H14A 109.5 .
C13 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C13 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C30 C31 C32 119.1(4) .
C30 C31 H31A 120.4 .
C32 C31 H31A 120.4 .
C6 C7 C8 119.9(4) .
C6 C7 H7A 120.1 .
C8 C7 H7A 120.1 .
C22 C24 H24A 109.5 .
C22 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
C22 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
C22 C23 H23A 109.5 .
C22 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C22 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C10 C12 H12A 109.5 .
C10 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C10 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C13 C15 H15A 109.5 .
C13 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
C13 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 C28 2.128(4) .
Mn1 C1 2.235(4) .
Mn1 Cl1 2.4579(15) .
Mn1 Cl1 2.4669(14) 3_657
Cl1 Mn1 2.4669(14) 3_657
N2 C1 1.368(4) .
N2 C3 1.398(4) .
N2 C16 1.452(5) .
N1 C1 1.367(5) .
N1 C2 1.393(4) .
N1 C4 1.447(5) .
C16 C21 1.407(5) .
C16 C17 1.421(5) .
C4 C9 1.410(5) .
C4 C5 1.423(5) .
C21 C20 1.397(5) .
C21 C25 1.548(5) .
C28 C33 1.399(6) .
C28 C29 1.410(5) .
C17 C18 1.402(6) .
C17 C22 1.524(5) .
C9 C8 1.383(6) .
C9 C13 1.540(5) .
C3 C2 1.342(5) .
C3 H3A 0.9500 .
C25 C27 1.518(5) .
C25 C26 1.556(5) .
C25 H25A 1.0000 .
C18 C19 1.379(6) .
C18 H18A 0.9500 .
C5 C6 1.382(6) .
C5 C10 1.538(6) .
C20 C19 1.409(5) .
C20 H20A 0.9500 .
C19 H19A 0.9500 .
C13 C14 1.529(5) .
C13 C15 1.544(6) .
C13 H13A 1.0000 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C2 H2A 0.9500 .
C22 C24 1.535(5) .
C22 C23 1.557(5) .
C22 H22A 1.0000 .
C29 C30 1.412(5) .
C29 H29A 0.9500 .
C33 C32 1.403(5) .
C33 H33A 0.9500 .
C32 C31 1.403(6) .
C32 H32A 0.9500 .
C6 C7 1.381(7) .
C6 H6A 0.9500 .
C8 C7 1.410(7) .
C8 H8A 0.9500 .
C30 C31 1.387(7) .
C30 H30A 0.9500 .
C10 C11 1.528(6) .
C10 C12 1.549(6) .
C10 H10A 1.0000 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C31 H31A 0.9500 .
C7 H7A 0.9500 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
