#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:25:42 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179843 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/39/7013907.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_7013907
loop_
_publ_author_name
'Reddig, Nicole'
'Pursche, Daniel'
'Rompel, Annette'
_publ_section_title
;
 Unique example of flexible phenol coordination in mononuclear
 manganese compounds.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1474
_journal_page_last               1480
_journal_paper_doi               10.1039/b316305a
_journal_year                    2004
_chemical_formula_sum            'C25 H17 Cl4 Mn N4 O5'
_chemical_formula_weight         650.17
_chemical_name_common
;
Manganese(iii)-tetrachlorocatechol-2-((bis(pyridin-2-
ylmethyl)amino)methyl) -4-nitrophenol
;
_chemical_name_systematic
;
Manganese(III)-tetrachlorocatechol-2-((bis(pyridin-2-ylmethyl)amino)methyl)
-4-nitrophenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4866(3)
_cell_length_b                   13.9788(4)
_cell_length_c                   14.9053(4)
_cell_measurement_temperature    200(2)
_cell_volume                     2601.69(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      200(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker AXS SMART 6000 CCD'
_diffrn_measurement_method       'combined omega theta-scan'
_diffrn_radiation_monochromator  'Goebel mirrow'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_av_sigmaI/netI    0.0759
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15421
_diffrn_reflns_theta_full        71.85
_diffrn_reflns_theta_max         71.85
_diffrn_reflns_theta_min         4.34
_exptl_absorpt_coefficient_mu    8.307
_exptl_absorpt_correction_type   'SADABS software package, Bruker AXS'
_exptl_crystal_colour            'reddish brown'
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needles
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(7)
_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     352
_refine_ls_number_reflns         4854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0920P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                4175
_reflns_number_total             4854
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b316305a.txt
_cod_data_source_block           p212121
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7013907
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Mn1 Mn 0.13179(6) 0.58357(5) 0.20956(5) 0.02449(18) Uani 1 1 d . . .
Cl1 Cl 0.31303(15) 0.79075(12) 0.42369(11) 0.0631(5) Uani 1 1 d . . .
Cl2 Cl 0.56372(16) 0.76115(13) 0.41582(16) 0.0792(7) Uani 1 1 d . . .
Cl3 Cl 0.66056(12) 0.62795(15) 0.26688(16) 0.0766(6) Uani 1 1 d . . .
Cl4 Cl 0.50712(12) 0.50179(12) 0.15011(12) 0.0596(4) Uani 1 1 d . . .
O1 O -0.0036(3) 0.6238(2) 0.2468(2) 0.0296(7) Uani 1 1 d . . .
O2 O 0.1966(3) 0.6800(2) 0.2831(2) 0.0311(7) Uani 1 1 d . . .
O3 O 0.2733(3) 0.5519(2) 0.1763(2) 0.0313(7) Uani 1 1 d . . .
O4 O -0.3211(4) 0.3972(3) 0.4892(3) 0.0518(11) Uani 1 1 d . . .
O5 O -0.3172(3) 0.3045(3) 0.3739(3) 0.0485(10) Uani 1 1 d . . .
N1 N 0.0646(3) 0.4529(3) 0.1475(3) 0.0301(9) Uani 1 1 d . . .
N2 N 0.0977(3) 0.6248(3) 0.0682(3) 0.0312(9) Uani 1 1 d . . .
N3 N 0.1399(3) 0.4751(3) 0.3173(3) 0.0304(9) Uani 1 1 d . . .
N4 N -0.2871(4) 0.3757(3) 0.4144(3) 0.0374(10) Uani 1 1 d . . .
C1 C 0.0967(4) 0.4527(4) 0.0514(3) 0.0367(12) Uani 1 1 d . . .
H1A H 0.0510 0.4073 0.0178 0.044 Uiso 1 1 calc R . .
H1B H 0.1719 0.4309 0.0461 0.044 Uiso 1 1 calc R . .
C2 C 0.0861(4) 0.5503(4) 0.0116(3) 0.0343(11) Uani 1 1 d . . .
C3 C 0.0947(4) 0.7119(4) 0.0345(4) 0.0373(12) Uani 1 1 d . . .
H3A H 0.1015 0.7645 0.0745 0.045 Uiso 1 1 calc R . .
C4 C 0.0819(5) 0.7310(5) -0.0571(4) 0.0475(15) Uani 1 1 d . . .
H4A H 0.0814 0.7949 -0.0789 0.057 Uiso 1 1 calc R . .
C5 C 0.0702(5) 0.6555(5) -0.1142(4) 0.0509(16) Uani 1 1 d . . .
H5A H 0.0624 0.6661 -0.1768 0.061 Uiso 1 1 calc R . .
C6 C 0.0699(5) 0.5634(5) -0.0806(4) 0.0457(14) Uani 1 1 d . . .
H6A H 0.0589 0.5101 -0.1191 0.055 Uiso 1 1 calc R . .
C7 C 0.1097(4) 0.3673(3) 0.1932(3) 0.0358(11) Uani 1 1 d . . .
H7A H 0.1802 0.3515 0.1666 0.043 Uiso 1 1 calc R . .
H7B H 0.0615 0.3120 0.1836 0.043 Uiso 1 1 calc R . .
C8 C 0.1229(4) 0.3842(3) 0.2921(3) 0.0313(10) Uani 1 1 d . . .
C9 C 0.1551(4) 0.4949(4) 0.4046(3) 0.0366(11) Uani 1 1 d . . .
H9A H 0.1650 0.5594 0.4226 0.044 Uiso 1 1 calc R . .
C10 C 0.1566(4) 0.4239(5) 0.4687(4) 0.0445(14) Uani 1 1 d . . .
H10A H 0.1683 0.4394 0.5299 0.053 Uiso 1 1 calc R . .
C11 C 0.1411(5) 0.3313(5) 0.4434(4) 0.0484(15) Uani 1 1 d . . .
H11A H 0.1419 0.2818 0.4871 0.058 Uiso 1 1 calc R . .
C12 C 0.1242(4) 0.3096(4) 0.3542(4) 0.0418(12) Uani 1 1 d . . .
H12A H 0.1137 0.2453 0.3355 0.050 Uiso 1 1 calc R . .
C13 C -0.0561(4) 0.4561(4) 0.1522(3) 0.0314(10) Uani 1 1 d . . .
H13A H -0.0851 0.3942 0.1311 0.038 Uiso 1 1 calc R . .
H13B H -0.0824 0.5065 0.1110 0.038 Uiso 1 1 calc R . .
C14 C -0.0987(4) 0.4759(3) 0.2454(3) 0.0283(10) Uani 1 1 d . . .
C15 C -0.0686(3) 0.5611(3) 0.2883(3) 0.0267(9) Uani 1 1 d . . .
C16 C -0.1080(4) 0.5823(4) 0.3747(3) 0.0330(10) Uani 1 1 d . . .
H16A H -0.0865 0.6395 0.4039 0.040 Uiso 1 1 calc R . .
C17 C -0.1774(4) 0.5203(3) 0.4170(3) 0.0327(11) Uani 1 1 d . . .
H17A H -0.2032 0.5338 0.4756 0.039 Uiso 1 1 calc R . .
C18 C -0.2088(4) 0.4383(3) 0.3725(3) 0.0272(10) Uani 1 1 d . . .
C19 C -0.1691(4) 0.4143(3) 0.2878(3) 0.0294(9) Uani 1 1 d . . .
H19A H -0.1903 0.3563 0.2596 0.035 Uiso 1 1 calc R . .
C20 C 0.3033(4) 0.6686(3) 0.2856(3) 0.0300(10) Uani 1 1 d . . .
C21 C 0.3703(5) 0.7163(4) 0.3448(4) 0.0407(12) Uani 1 1 d . . .
C22 C 0.4814(5) 0.7028(4) 0.3408(5) 0.0509(16) Uani 1 1 d . . .
C23 C 0.5237(4) 0.6424(4) 0.2775(5) 0.0473(15) Uani 1 1 d . . .
C24 C 0.4564(4) 0.5877(4) 0.2204(4) 0.0391(11) Uani 1 1 d . . .
C25 C 0.3460(4) 0.6003(3) 0.2259(3) 0.0302(10) Uani 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 0.0181 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 175.34(15) . . ?
O1 Mn1 O2 90.03(15) . . ?
O3 Mn1 O2 85.39(15) . . ?
O1 Mn1 N3 91.85(15) . . ?
O3 Mn1 N3 89.26(15) . . ?
O2 Mn1 N3 92.76(14) . . ?
O1 Mn1 N1 91.72(15) . . ?
O3 Mn1 N1 92.94(15) . . ?
O2 Mn1 N1 168.48(15) . . ?
N3 Mn1 N1 75.81(14) . . ?
O1 Mn1 N2 91.73(15) . . ?
O3 Mn1 N2 89.49(15) . . ?
O2 Mn1 N2 116.08(15) . . ?
N3 Mn1 N2 150.93(15) . . ?
N1 Mn1 N2 75.26(15) . . ?
C15 O1 Mn1 119.1(3) . . ?
C20 O2 Mn1 110.6(3) . . ?
C25 O3 Mn1 111.6(3) . . ?
C1 N1 C7 109.7(4) . . ?
C1 N1 C13 108.3(4) . . ?
C7 N1 C13 112.4(4) . . ?
C1 N1 Mn1 107.6(3) . . ?
C7 N1 Mn1 109.2(3) . . ?
C13 N1 Mn1 109.5(3) . . ?
C3 N2 C2 118.2(4) . . ?
C3 N2 Mn1 127.3(4) . . ?
C2 N2 Mn1 114.4(3) . . ?
C8 N3 C9 119.2(4) . . ?
C8 N3 Mn1 116.1(3) . . ?
C9 N3 Mn1 124.7(4) . . ?
O5 N4 O4 122.6(4) . . ?
O5 N4 C18 119.0(4) . . ?
O4 N4 C18 118.4(4) . . ?
N1 C1 C2 110.9(4) . . ?
N2 C2 C6 121.9(5) . . ?
N2 C2 C1 116.6(4) . . ?
C6 C2 C1 121.5(5) . . ?
N2 C3 C4 123.4(5) . . ?
C5 C4 C3 118.2(6) . . ?
C4 C5 C6 119.7(5) . . ?
C5 C6 C2 118.5(6) . . ?
N1 C7 C8 111.4(4) . . ?
N3 C8 C12 121.4(5) . . ?
N3 C8 C7 116.1(4) . . ?
C12 C8 C7 122.3(5) . . ?
N3 C9 C10 121.7(5) . . ?
C11 C10 C9 119.4(5) . . ?
C10 C11 C12 119.8(5) . . ?
C11 C12 C8 118.5(5) . . ?
N1 C13 C14 113.5(4) . . ?
C19 C14 C15 119.4(4) . . ?
C19 C14 C13 121.9(4) . . ?
C15 C14 C13 118.7(4) . . ?
O1 C15 C14 120.3(4) . . ?
O1 C15 C16 119.6(4) . . ?
C14 C15 C16 120.1(4) . . ?
C17 C16 C15 120.4(4) . . ?
C16 C17 C18 118.7(4) . . ?
C17 C18 C19 122.2(4) . . ?
C17 C18 N4 119.0(4) . . ?
C19 C18 N4 118.8(4) . . ?
C14 C19 C18 119.2(4) . . ?
O2 C20 C21 124.0(5) . . ?
O2 C20 C25 116.0(4) . . ?
C21 C20 C25 120.0(5) . . ?
C20 C21 C22 120.4(6) . . ?
C20 C21 Cl1 118.3(4) . . ?
C22 C21 Cl1 121.4(5) . . ?
C23 C22 C21 119.6(5) . . ?
C23 C22 Cl2 120.5(5) . . ?
C21 C22 Cl2 119.9(6) . . ?
C22 C23 C24 121.1(5) . . ?
C22 C23 Cl3 121.1(5) . . ?
C24 C23 Cl3 117.8(5) . . ?
C25 C24 C23 118.9(5) . . ?
C25 C24 Cl4 119.3(4) . . ?
C23 C24 Cl4 121.7(4) . . ?
O3 C25 C24 124.7(5) . . ?
O3 C25 C20 115.5(4) . . ?
C24 C25 C20 119.8(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 O1 1.866(3) . ?
Mn1 O3 1.887(3) . ?
Mn1 O2 1.917(3) . ?
Mn1 N3 2.210(4) . ?
Mn1 N1 2.212(4) . ?
Mn1 N2 2.225(4) . ?
Cl1 C21 1.726(6) . ?
Cl2 C22 1.724(6) . ?
Cl3 C23 1.728(5) . ?
Cl4 C24 1.715(6) . ?
O1 C15 1.346(5) . ?
O2 C20 1.342(6) . ?
O3 C25 1.352(6) . ?
O4 N4 1.231(6) . ?
O5 N4 1.223(6) . ?
N1 C1 1.487(6) . ?
N1 C7 1.488(6) . ?
N1 C13 1.510(6) . ?
N2 C3 1.318(7) . ?
N2 C2 1.349(7) . ?
N3 C8 1.342(6) . ?
N3 C9 1.344(6) . ?
N4 C18 1.452(6) . ?
C1 C2 1.493(8) . ?
C2 C6 1.401(7) . ?
C3 C4 1.401(8) . ?
C4 C5 1.364(9) . ?
C5 C6 1.381(9) . ?
C7 C8 1.502(7) . ?
C8 C12 1.394(7) . ?
C9 C10 1.377(7) . ?
C10 C11 1.362(9) . ?
C11 C12 1.380(8) . ?
C13 C14 1.514(6) . ?
C14 C19 1.384(6) . ?
C14 C15 1.403(7) . ?
C15 C16 1.409(7) . ?
C16 C17 1.378(7) . ?
C17 C18 1.381(7) . ?
C18 C19 1.398(7) . ?
C20 C21 1.387(7) . ?
C20 C25 1.410(7) . ?
C21 C22 1.401(9) . ?
C22 C23 1.371(10) . ?
C23 C24 1.420(8) . ?
C24 C25 1.393(7) . ?
