#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:25:42 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179843 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/39/7013905.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_7013905
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            'C20 H22 Cl2 Mn N4 O4'
_chemical_formula_weight         508.26
_chemical_name_common
;Manganese(ii)-di-chloro-2-((bis(pyridin-2-
ylmethyl)amino)methyl)-4-nitrophenol
;
_chemical_name_systematic
;
Manganese(II)-di-chloro-2-((bis(pyridin-2-ylmethyl)amino)methyl)-4-nitrophenol
;
_space_group_IT_number           2
_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                97.941(2)
_cell_angle_beta                 92.761(2)
_cell_angle_gamma                98.723(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4619(3)
_cell_length_b                   9.4354(3)
_cell_length_c                   16.1153(5)
_cell_measurement_temperature    200(2)
_cell_volume                     1107.96(7)
_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, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.857
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD'
_diffrn_measurement_method       'combined omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6537
_diffrn_reflns_theta_full        25.92
_diffrn_reflns_theta_max         25.92
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_type   'SADABS software package, Bruker AXS'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needles
_exptl_crystal_F_000             522
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0977P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                2905
_reflns_number_total             3706
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b316305a.txt
_cod_data_source_block           p-1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7013905
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.39571(8) 0.13191(6) 0.77313(4) 0.0263(2) Uani 1 1 d . . .
Cl1 Cl 0.39468(15) -0.02252(11) 0.87691(7) 0.0330(3) Uani 1 1 d . . .
Cl2 Cl 0.12232(14) 0.10689(11) 0.68974(7) 0.0306(3) Uani 1 1 d . . .
O1 O 0.7920(4) 0.6486(3) 0.84170(19) 0.0319(7) Uani 1 1 d . . .
H1A H 0.7999 0.7381 0.8574 0.048 Uiso 1 1 calc R . .
O2 O 1.1713(5) 0.4110(3) 0.5296(2) 0.0426(8) Uani 1 1 d . . .
O3 O 1.2956(5) 0.6346(4) 0.5442(2) 0.0499(10) Uani 1 1 d . . .
N1 N 0.5680(4) 0.3196(3) 0.72167(19) 0.0202(7) Uani 1 1 d . . .
N2 N 0.5657(5) 0.0311(4) 0.6782(2) 0.0257(7) Uani 1 1 d . . .
N3 N 0.3657(4) 0.3347(4) 0.8575(2) 0.0246(7) Uani 1 1 d . . .
N4 N 1.1910(5) 0.5357(4) 0.5660(2) 0.0279(8) Uani 1 1 d . . .
C1 C 0.5727(5) 0.2637(4) 0.6319(2) 0.0240(8) Uani 1 1 d . . .
H1B H 0.6625 0.3297 0.6062 0.029 Uiso 1 1 calc R . .
H1C H 0.4519 0.2609 0.6029 0.029 Uiso 1 1 calc R . .
C2 C 0.6225(5) 0.1147(4) 0.6203(2) 0.0225(8) Uani 1 1 d . . .
C3 C 0.5993(6) -0.1060(5) 0.6683(3) 0.0329(10) Uani 1 1 d . . .
H3A H 0.5587 -0.1653 0.7089 0.039 Uiso 1 1 calc R . .
C4 C 0.6887(6) -0.1655(5) 0.6031(3) 0.0349(10) Uani 1 1 d . . .
H4A H 0.7086 -0.2633 0.5983 0.042 Uiso 1 1 calc R . .
C5 C 0.7489(6) -0.0777(5) 0.5446(3) 0.0344(10) Uani 1 1 d . . .
H5A H 0.8116 -0.1146 0.4985 0.041 Uiso 1 1 calc R . .
C6 C 0.7169(6) 0.0639(5) 0.5538(3) 0.0294(9) Uani 1 1 d . . .
H6A H 0.7595 0.1258 0.5148 0.035 Uiso 1 1 calc R . .
C7 C 0.4612(5) 0.4389(4) 0.7348(2) 0.0217(8) Uani 1 1 d . . .
H7A H 0.3564 0.4200 0.6925 0.026 Uiso 1 1 calc R . .
H7B H 0.5377 0.5306 0.7268 0.026 Uiso 1 1 calc R . .
C8 C 0.3931(5) 0.4550(4) 0.8214(2) 0.0232(8) Uani 1 1 d . . .
C9 C 0.2967(6) 0.3420(5) 0.9331(3) 0.0312(9) Uani 1 1 d . . .
H9A H 0.2807 0.2575 0.9596 0.037 Uiso 1 1 calc R . .
C10 C 0.2482(7) 0.4679(5) 0.9740(3) 0.0379(11) Uani 1 1 d . . .
H10A H 0.1976 0.4697 1.0271 0.045 Uiso 1 1 calc R . .
C11 C 0.2753(7) 0.5910(5) 0.9356(3) 0.0405(11) Uani 1 1 d . . .
H11A H 0.2417 0.6787 0.9619 0.049 Uiso 1 1 calc R . .
C12 C 0.3510(6) 0.5864(5) 0.8594(3) 0.0315(10) Uani 1 1 d . . .
H12A H 0.3741 0.6710 0.8332 0.038 Uiso 1 1 calc R . .
C13 C 0.7549(5) 0.3585(4) 0.7653(2) 0.0202(8) Uani 1 1 d . . .
H13A H 0.8152 0.2715 0.7583 0.024 Uiso 1 1 calc R . .
H13B H 0.7431 0.3857 0.8261 0.024 Uiso 1 1 calc R . .
C14 C 0.8752(5) 0.4804(4) 0.7343(2) 0.0197(8) Uani 1 1 d . . .
C15 C 0.8896(5) 0.6256(4) 0.7741(2) 0.0224(8) Uani 1 1 d . . .
C16 C 0.9989(6) 0.7382(4) 0.7435(2) 0.0253(8) Uani 1 1 d . . .
H16A H 1.0056 0.8351 0.7705 0.030 Uiso 1 1 calc R . .
C17 C 1.0954(5) 0.7099(4) 0.6754(3) 0.0261(9) Uani 1 1 d . . .
H17A H 1.1681 0.7865 0.6540 0.031 Uiso 1 1 calc R . .
C18 C 1.0863(5) 0.5676(4) 0.6375(2) 0.0219(8) Uani 1 1 d . . .
C19 C 0.9787(5) 0.4536(4) 0.6668(2) 0.0215(8) Uani 1 1 d . . .
H19A H 0.9766 0.3569 0.6403 0.026 Uiso 1 1 calc R . .
O4 O 0.7840(4) 0.9137(3) 0.9098(2) 0.0421(8) Uani 1 1 d . . .
H4 H 0.6749 0.9261 0.9083 0.063 Uiso 1 1 calc R . .
C20 C 0.8973(8) 1.0470(6) 0.9068(4) 0.0548(14) Uani 1 1 d . . .
H20A H 0.8821 1.1165 0.9561 0.082 Uiso 1 1 calc R . .
H20B H 0.8640 1.0850 0.8556 0.082 Uiso 1 1 calc R . .
H20C H 1.0244 1.0319 0.9067 0.082 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'
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
N3 Mn1 N2 145.07(13) . . ?
N3 Mn1 N1 73.61(12) . . ?
N2 Mn1 N1 73.39(12) . . ?
N3 Mn1 Cl2 97.87(9) . . ?
N2 Mn1 Cl2 99.32(9) . . ?
N1 Mn1 Cl2 100.97(8) . . ?
N3 Mn1 Cl1 97.69(9) . . ?
N2 Mn1 Cl1 101.94(9) . . ?
N1 Mn1 Cl1 143.45(9) . . ?
Cl2 Mn1 Cl1 115.48(4) . . ?
C7 N1 C1 112.0(3) . . ?
C7 N1 C13 112.6(3) . . ?
C1 N1 C13 112.1(3) . . ?
C7 N1 Mn1 104.0(2) . . ?
C1 N1 Mn1 103.4(2) . . ?
C13 N1 Mn1 112.1(2) . . ?
C3 N2 C2 117.9(4) . . ?
C3 N2 Mn1 127.1(3) . . ?
C2 N2 Mn1 114.7(3) . . ?
C8 N3 C9 118.6(4) . . ?
C8 N3 Mn1 114.3(3) . . ?
C9 N3 Mn1 126.1(3) . . ?
O2 N4 O3 122.6(4) . . ?
O2 N4 C18 118.7(3) . . ?
O3 N4 C18 118.6(4) . . ?
N1 C1 C2 111.1(3) . . ?
N2 C2 C6 121.7(4) . . ?
N2 C2 C1 115.6(3) . . ?
C6 C2 C1 122.7(4) . . ?
N2 C3 C4 124.0(4) . . ?
C3 C4 C5 117.5(4) . . ?
C6 C5 C4 119.4(4) . . ?
C2 C6 C5 119.4(4) . . ?
N1 C7 C8 111.5(3) . . ?
N3 C8 C12 122.2(4) . . ?
N3 C8 C7 116.4(3) . . ?
C12 C8 C7 121.3(4) . . ?
N3 C9 C10 122.6(4) . . ?
C11 C10 C9 118.2(4) . . ?
C12 C11 C10 119.9(4) . . ?
C11 C12 C8 118.4(4) . . ?
N1 C13 C14 114.8(3) . . ?
C19 C14 C15 117.6(3) . . ?
C19 C14 C13 120.8(3) . . ?
C15 C14 C13 121.5(3) . . ?
O1 C15 C16 122.5(3) . . ?
O1 C15 C14 116.6(3) . . ?
C16 C15 C14 120.9(3) . . ?
C17 C16 C15 120.5(4) . . ?
C16 C17 C18 119.0(4) . . ?
C17 C18 C19 121.6(4) . . ?
C17 C18 N4 119.6(3) . . ?
C19 C18 N4 118.8(4) . . ?
C14 C19 C18 120.3(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 N3 2.236(3) . ?
Mn1 N2 2.237(3) . ?
Mn1 N1 2.301(3) . ?
Mn1 Cl2 2.3505(12) . ?
Mn1 Cl1 2.3648(11) . ?
O1 C15 1.351(5) . ?
O2 N4 1.225(5) . ?
O3 N4 1.225(5) . ?
N1 C7 1.474(5) . ?
N1 C1 1.474(5) . ?
N1 C13 1.501(5) . ?
N2 C3 1.344(5) . ?
N2 C2 1.346(5) . ?
N3 C8 1.339(5) . ?
N3 C9 1.342(5) . ?
N4 C18 1.446(5) . ?
C1 C2 1.497(5) . ?
C2 C6 1.381(6) . ?
C3 C4 1.371(6) . ?
C4 C5 1.387(7) . ?
C5 C6 1.382(6) . ?
C7 C8 1.504(5) . ?
C8 C12 1.392(5) . ?
C9 C10 1.383(6) . ?
C10 C11 1.383(7) . ?
C11 C12 1.375(7) . ?
C13 C14 1.505(5) . ?
C14 C19 1.381(5) . ?
C14 C15 1.416(5) . ?
C15 C16 1.399(5) . ?
C16 C17 1.360(6) . ?
C17 C18 1.386(5) . ?
C18 C19 1.393(5) . ?
O4 C20 1.413(6) . ?
