#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:53:44 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179216 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/43/4314389.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_4314389
loop_
_publ_author_name
'Michael U. Triller'
'Daniel Pursche'
'Wen-Yuan Hsieh'
'Vincent L. Pecoraro'
'Annette Rompel'
'Bernt Krebs'
_publ_section_title
;
 Catalytic Oxidation of 3,5-Di-tert-butylcatechol by a Series of
 Mononuclear Manganese Complexes: Synthesis, Structure, and Kinetic
 Investigation
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6274
_journal_page_last               6283
_journal_paper_doi               10.1021/ic0347788
_journal_volume                  42
_journal_year                    2003
_chemical_formula_moiety         '[Mn(mimppa)(tcc)] . 2 CHCl3'
_chemical_formula_sum            'C25 H19 Cl10 Mn N4 O3'
_chemical_formula_weight         832.88
_chemical_melting_point          493
_chemical_name_common            'manganese(III)tetrachlorocatechol monomer'
_chemical_name_systematic
; 
 manganesetetrachlorocatechol((1-methylimidazol-2-yl)methyl)
((2-pyridyl)methyl)-2-hydroxyphenylamine) 
;
_space_group_IT_number           14
_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                 101.50(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.417(3)
_cell_length_b                   13.930(3)
_cell_length_c                   17.497(3)
_cell_measurement_temperature    100(2)
_cell_volume                     3204.5(12)
_computing_cell_refinement       'SMART/SAINT software package, Bruker Nonius'
_computing_data_collection       'SMART software package, Bruker Nonius'
_computing_data_reduction
'G. M. Sheldrick, Shelxltl Plus, Siemens Analytical X-ray Instruments 1990'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker AXS Smart 6000 CCD'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.1035
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18412
_diffrn_reflns_theta_full        71.63
_diffrn_reflns_theta_max         71.63
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    11.342
_exptl_absorpt_correction_type
'Program sadabs, SAINT software package, Bruker Nonius, Karlsruhe'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.831
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0298P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                3739
_reflns_number_total             5971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0347788si20030711_042806_5.cif
_cod_data_source_block           complex6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3204.5(11)
_cod_database_code               4314389
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.12807(5) 0.61884(5) 0.16599(4) 0.01434(15) Uani 1 1 d . . .
O1 O -0.01035(19) 0.64527(18) 0.14585(15) 0.0160(6) Uani 1 1 d . . .
O2 O 0.14845(19) 0.72449(18) 0.09740(15) 0.0175(6) Uani 1 1 d . . .
O3 O 0.27017(19) 0.60065(18) 0.18031(15) 0.0171(6) Uani 1 1 d . . .
N1 N 0.0865(3) 0.5259(2) 0.26456(19) 0.0214(8) Uani 1 1 d . . .
N2 N 0.1049(2) 0.4783(2) 0.1180(2) 0.0215(8) Uani 1 1 d . . .
N3 N 0.0678(3) 0.3241(3) 0.1220(2) 0.0329(10) Uani 1 1 d . . .
N4 N 0.1520(2) 0.7098(3) 0.2735(2) 0.0230(9) Uani 1 1 d . . .
C1 C 0.1021(3) 0.4216(3) 0.2494(3) 0.0321(12) Uani 1 1 d . . .
H1A H 0.1708 0.4012 0.2763 0.038 Uiso 1 1 calc R . .
H1B H 0.0513 0.3823 0.2694 0.038 Uiso 1 1 calc R . .
C2 C 0.0904(3) 0.4083(3) 0.1642(3) 0.0259(11) Uani 1 1 d . . .
C3 C 0.0935(3) 0.4400(3) 0.0450(3) 0.0269(11) Uani 1 1 d . . .
H3A H 0.1009 0.4749 -0.0002 0.032 Uiso 1 1 calc R . .
C4 C 0.0704(3) 0.3457(3) 0.0457(2) 0.0265(11) Uani 1 1 d . . .
H4A H 0.0583 0.3031 0.0024 0.032 Uiso 1 1 calc R . .
C5 C 0.0476(4) 0.2339(3) 0.1523(3) 0.0492(15) Uani 1 1 d . . .
H5A H 0.0506 0.2395 0.2086 0.074 Uiso 1 1 calc R . .
H5B H 0.0985 0.1873 0.1429 0.074 Uiso 1 1 calc R . .
H5C H -0.0203 0.2121 0.1266 0.074 Uiso 1 1 calc R . .
C6 C 0.1462(3) 0.5581(3) 0.3393(2) 0.0279(11) Uani 1 1 d . . .
H6A H 0.2164 0.5330 0.3462 0.034 Uiso 1 1 calc R . .
H6B H 0.1155 0.5335 0.3824 0.034 Uiso 1 1 calc R . .
C7 C 0.1480(3) 0.6650(3) 0.3410(2) 0.0254(11) Uani 1 1 d . . .
C8 C 0.1503(3) 0.7155(3) 0.4098(3) 0.0350(13) Uani 1 1 d . . .
H8A H 0.1458 0.6828 0.4566 0.042 Uiso 1 1 calc R . .
C9 C 0.1588(3) 0.8108(3) 0.4088(3) 0.0371(13) Uani 1 1 d . . .
H9A H 0.1607 0.8464 0.4553 0.045 Uiso 1 1 calc R . .
C10 C 0.1649(3) 0.8588(3) 0.3394(3) 0.0258(11) Uani 1 1 d . . .
H10A H 0.1724 0.9266 0.3383 0.031 Uiso 1 1 calc R . .
C11 C 0.1598(3) 0.8048(3) 0.2737(3) 0.0292(11) Uani 1 1 d . . .
H11A H 0.1619 0.8366 0.2261 0.035 Uiso 1 1 calc R . .
C12 C -0.0224(3) 0.5479(3) 0.2559(2) 0.0170(9) Uani 1 1 d . . .
C13 C -0.0797(3) 0.5113(3) 0.3074(2) 0.0243(11) Uani 1 1 d . . .
H13A H -0.0489 0.4700 0.3486 0.029 Uiso 1 1 calc R . .
C14 C -0.1811(3) 0.5351(3) 0.2988(3) 0.0268(11) Uani 1 1 d . . .
H14A H -0.2202 0.5111 0.3343 0.032 Uiso 1 1 calc R . .
C15 C -0.2253(3) 0.5943(3) 0.2379(3) 0.0246(11) Uani 1 1 d . . .
H15A H -0.2953 0.6103 0.2315 0.029 Uiso 1 1 calc R . .
C16 C -0.1689(3) 0.6304(3) 0.1862(2) 0.0208(10) Uani 1 1 d . . .
H16A H -0.2009 0.6700 0.1443 0.025 Uiso 1 1 calc R . .
C17 C -0.0654(3) 0.6091(3) 0.1950(2) 0.0155(9) Uani 1 1 d . . .
Cl1 Cl 0.49284(8) 0.58354(7) 0.19567(6) 0.0230(2) Uani 1 1 d . . .
Cl2 Cl 0.58707(8) 0.74820(8) 0.10723(7) 0.0312(3) Uani 1 1 d . . .
Cl3 Cl 0.44077(8) 0.89405(7) 0.00353(6) 0.0218(2) Uani 1 1 d . . .
Cl4 Cl 0.20559(8) 0.88285(7) -0.00145(6) 0.0234(2) Uani 1 1 d . . .
C18 C 0.2470(3) 0.7338(3) 0.0967(2) 0.0145(9) Uani 1 1 d . . .
C19 C 0.3141(3) 0.6674(3) 0.1423(2) 0.0149(9) Uani 1 1 d . . .
C20 C 0.4164(3) 0.6717(3) 0.1433(2) 0.0156(9) Uani 1 1 d . . .
C21 C 0.4568(3) 0.7416(3) 0.1018(2) 0.0171(9) Uani 1 1 d . . .
C22 C 0.3926(3) 0.8069(3) 0.0576(2) 0.0183(10) Uani 1 1 d . . .
C23 C 0.2883(3) 0.8023(3) 0.0552(2) 0.0154(9) Uani 1 1 d . . .
Cl5 Cl 0.91331(9) 0.86999(8) 0.20326(7) 0.0326(3) Uani 1 1 d . . .
Cl6 Cl 1.02890(10) 0.98220(8) 0.11288(8) 0.0420(3) Uani 1 1 d . . .
Cl7 Cl 0.85507(10) 0.87218(9) 0.03561(7) 0.0485(4) Uani 1 1 d . . .
C24 C 0.9590(3) 0.8762(3) 0.1162(2) 0.0278(11) Uani 1 1 d . . .
H24A H 1.0043 0.8198 0.1134 0.033 Uiso 1 1 calc R . .
Cl8 Cl 0.64967(13) 0.29278(10) 0.13210(9) 0.0662(5) Uani 1 1 d . . .
Cl9 Cl 0.82576(10) 0.37604(10) 0.08857(9) 0.0534(4) Uani 1 1 d . . .
Cl10 Cl 0.62878(11) 0.45942(10) 0.03420(8) 0.0573(4) Uani 1 1 d . . .
C25 C 0.7066(4) 0.3996(3) 0.1114(3) 0.0364(13) Uani 1 1 d . . .
H25A H 0.7166 0.4416 0.1586 0.044 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 '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 Mn1 O3 174.98(11) . . ?
O1 Mn1 O2 89.49(11) . . ?
O3 Mn1 O2 85.49(11) . . ?
O1 Mn1 N2 92.62(12) . . ?
O3 Mn1 N2 89.60(12) . . ?
O2 Mn1 N2 118.55(13) . . ?
O1 Mn1 N4 91.02(12) . . ?
O3 Mn1 N4 89.57(12) . . ?
O2 Mn1 N4 94.34(13) . . ?
N2 Mn1 N4 146.92(14) . . ?
O1 Mn1 N1 82.63(12) . . ?
O3 Mn1 N1 102.30(12) . . ?
O2 Mn1 N1 164.75(12) . . ?
N2 Mn1 N1 75.03(13) . . ?
N4 Mn1 N1 72.87(13) . . ?
C17 O1 Mn1 117.6(2) . . ?
C18 O2 Mn1 109.9(2) . . ?
C19 O3 Mn1 111.8(2) . . ?
C6 N1 C12 112.6(3) . . ?
C6 N1 C1 112.7(3) . . ?
C12 N1 C1 110.7(3) . . ?
C6 N1 Mn1 109.0(3) . . ?
C12 N1 Mn1 100.9(2) . . ?
C1 N1 Mn1 110.4(2) . . ?
C2 N2 C3 106.5(4) . . ?
C2 N2 Mn1 118.1(3) . . ?
C3 N2 Mn1 135.2(3) . . ?
C4 N3 C2 106.7(4) . . ?
C4 N3 C5 127.1(4) . . ?
C2 N3 C5 126.2(4) . . ?
C11 N4 C7 118.4(4) . . ?
C11 N4 Mn1 124.5(3) . . ?
C7 N4 Mn1 116.8(3) . . ?
C2 C1 N1 108.0(4) . . ?
N2 C2 N3 110.2(4) . . ?
N2 C2 C1 122.1(4) . . ?
N3 C2 C1 127.6(4) . . ?
C4 C3 N2 110.9(4) . . ?
C3 C4 N3 105.7(4) . . ?
N1 C6 C7 109.2(4) . . ?
N4 C7 C8 121.8(5) . . ?
N4 C7 C6 116.7(4) . . ?
C8 C7 C6 121.4(4) . . ?
C9 C8 C7 118.7(5) . . ?
C8 C9 C10 120.5(5) . . ?
C11 C10 C9 117.6(4) . . ?
N4 C11 C10 123.0(5) . . ?
C13 C12 C17 121.3(4) . . ?
C13 C12 N1 121.5(4) . . ?
C17 C12 N1 117.2(3) . . ?
C14 C13 C12 120.0(4) . . ?
C13 C14 C15 119.4(4) . . ?
C14 C15 C16 120.8(4) . . ?
C15 C16 C17 120.8(4) . . ?
O1 C17 C12 121.5(4) . . ?
O1 C17 C16 120.9(4) . . ?
C12 C17 C16 117.6(4) . . ?
O2 C18 C23 125.2(4) . . ?
O2 C18 C19 116.8(3) . . ?
C23 C18 C19 118.0(4) . . ?
O3 C19 C20 124.1(4) . . ?
O3 C19 C18 115.9(3) . . ?
C20 C19 C18 119.9(4) . . ?
C19 C20 C21 121.3(4) . . ?
C19 C20 Cl1 117.3(3) . . ?
C21 C20 Cl1 121.4(3) . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 Cl2 120.4(3) . . ?
C20 C21 Cl2 120.2(3) . . ?
C21 C22 C23 119.8(4) . . ?
C21 C22 Cl3 120.4(3) . . ?
C23 C22 Cl3 119.7(3) . . ?
C18 C23 C22 121.5(4) . . ?
C18 C23 Cl4 117.8(3) . . ?
C22 C23 Cl4 120.7(3) . . ?
Cl5 C24 Cl6 110.5(2) . . ?
Cl5 C24 Cl7 109.4(2) . . ?
Cl6 C24 Cl7 109.9(2) . . ?
Cl8 C25 Cl10 110.4(3) . . ?
Cl8 C25 Cl9 110.2(3) . . ?
Cl10 C25 Cl9 110.2(3) . . ?
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 O1 1.857(3) . ?
Mn1 O3 1.890(3) . ?
Mn1 O2 1.952(3) . ?
Mn1 N2 2.128(3) . ?
Mn1 N4 2.236(3) . ?
Mn1 N1 2.312(3) . ?
O1 C17 1.339(4) . ?
O2 C18 1.331(4) . ?
O3 C19 1.345(4) . ?
N1 C6 1.461(5) . ?
N1 C12 1.471(5) . ?
N1 C1 1.499(5) . ?
N2 C2 1.307(5) . ?
N2 C3 1.365(5) . ?
N3 C4 1.376(5) . ?
N3 C2 1.387(5) . ?
N3 C5 1.412(5) . ?
N4 C11 1.328(5) . ?
N4 C7 1.347(5) . ?
C1 C2 1.479(6) . ?
C3 C4 1.350(6) . ?
C6 C7 1.488(6) . ?
C7 C8 1.389(6) . ?
C8 C9 1.332(6) . ?
C9 C10 1.402(6) . ?
C10 C11 1.365(6) . ?
C12 C13 1.393(5) . ?
C12 C17 1.396(5) . ?
C13 C14 1.379(6) . ?
C14 C15 1.383(6) . ?
C15 C16 1.385(5) . ?
C16 C17 1.398(5) . ?
Cl1 C20 1.739(4) . ?
Cl2 C21 1.734(4) . ?
Cl3 C22 1.741(4) . ?
Cl4 C23 1.742(4) . ?
C18 C23 1.381(5) . ?
C18 C19 1.421(5) . ?
C19 C20 1.371(5) . ?
C20 C21 1.387(5) . ?
C21 C22 1.380(5) . ?
C22 C23 1.392(5) . ?
Cl5 C24 1.755(4) . ?
Cl6 C24 1.757(4) . ?
Cl7 C24 1.775(4) . ?
Cl8 C25 1.743(4) . ?
Cl9 C25 1.754(5) . ?
Cl10 C25 1.746(5) . ?
