#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:17:56 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179475 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/72/4337267.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_4337267
loop_
_publ_author_name
'Zampakou, Marianthi'
'Rizeq, Natalia'
'Tangoulis, Vassilis'
'Papadopoulos, Athanasios N.'
'Perdih, Franc'
'Turel, Iztok'
'Psomas, George'
_publ_section_title
;
 Manganese(II) Complexes with the Non-steroidal Anti-Inflammatory Drug
 Tolfenamic Acid: Structure and Biological Perspectives.
;
_journal_issue                   4
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2040
_journal_page_last               2052
_journal_paper_doi               10.1021/ic4025487
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C76 H62 Cl4 Mn2 N10 O8'
_chemical_formula_sum            'C76 H62 Cl4 Mn2 N10 O8'
_chemical_formula_weight         1495.04
_chemical_name_common
;        
bis(di(2-pyridyl)amine-N,N')-bis(μ₂-tolfenamato-O,O')-bis(tolfenamato-O,O')-di-manganese(II)
;
_chemical_name_systematic
;
bis(di(2-pyridyl)amine-N,N')-bis(μ₂-2-[(3-chloro-2-methylphenyl)amino]benzoato-O,O')-bis(2-[(3-chloro-2-methylphenyl)amino]benzoato-O,O')-di-manganese(II) 
;
_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                 104.966(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.8066(3)
_cell_length_b                   11.6969(2)
_cell_length_c                   20.8490(5)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3298
_cell_measurement_theta_min      2.7627
_cell_volume                     3488.38(13)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            33243
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.9443
_exptl_absorpt_correction_T_min  0.8452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1540
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         7982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0545
_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)+(0.0659P)²+2.6311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                5775
_reflns_number_total             7982
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic4025487_si_004.cif
_cod_data_source_block           mo25
_cod_original_cell_volume        3488.38(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4337267
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 0.49190(2) 0.19237(3) 0.01331(2) 0.03866(13) Uani 1 1 d .
Cl1 Cl 0.10035(11) -0.31702(11) 0.10105(10) 0.1331(6) Uani 1 1 d .
Cl2 Cl 0.06802(14) -0.51781(12) -0.27558(8) 0.1386(6) Uani 1 1 d .
N1 N 0.27475(18) 0.0676(2) 0.13777(14) 0.0577(7) Uani 1 1 d .
H1 H 0.3330 0.0687 0.1384 0.087 Uiso 1 1 calc R
N2 N 0.23790(17) -0.1890(2) -0.12806(18) 0.0719(9) Uani 1 1 d .
H2 H 0.2970 -0.1925 -0.1246 0.108 Uiso 1 1 calc R
N3 N 0.56672(16) 0.33423(18) 0.08034(12) 0.0448(5) Uani 1 1 d .
N4 N 0.56251(15) 0.27859(19) -0.05687(12) 0.0447(5) Uani 1 1 d .
N5 N 0.60383(16) 0.45418(19) -0.00048(12) 0.0476(6) Uani 1 1 d .
H5 H 0.6126 0.5250 -0.0081 0.071 Uiso 1 1 calc R
O1 O 0.39521(13) 0.15010(17) 0.07510(11) 0.0526(5) Uani 1 1 d .
O2 O 0.36060(13) 0.30593(15) 0.01519(10) 0.0482(5) Uani 1 1 d .
O3 O 0.40482(13) 0.09823(16) -0.06438(10) 0.0497(5) Uani 1 1 d .
O4 O 0.39500(13) -0.08916(17) -0.05944(13) 0.0626(6) Uani 1 1 d .
C1 C 0.34001(18) 0.2323(2) 0.05362(14) 0.0416(6) Uani 1 1 d .
C2 C 0.25011(18) 0.2420(2) 0.07264(14) 0.0432(6) Uani 1 1 d .
C3 C 0.1929(2) 0.3344(3) 0.04883(19) 0.0613(9) Uani 1 1 d .
H3 H 0.2122 0.3880 0.0221 0.074 Uiso 1 1 calc R
C4 C 0.1084(3) 0.3491(3) 0.0636(3) 0.0880(14) Uani 1 1 d .
H4 H 0.0719 0.4131 0.0484 0.106 Uiso 1 1 calc R
C5 C 0.0785(2) 0.2684(3) 0.1011(3) 0.0907(15) Uani 1 1 d .
H5A H 0.0207 0.2769 0.1104 0.109 Uiso 1 1 calc R
C6 C 0.1330(2) 0.1751(3) 0.1250(2) 0.0685(10) Uani 1 1 d .
H6 H 0.1116 0.1212 0.1505 0.082 Uiso 1 1 calc R
C7 C 0.2203(2) 0.1595(2) 0.11188(15) 0.0468(6) Uani 1 1 d .
C8 C 0.2388(2) -0.0299(2) 0.16378(16) 0.0515(7) Uani 1 1 d .
C9 C 0.1890(2) -0.1124(3) 0.12070(18) 0.0601(8) Uani 1 1 d .
C10 C 0.1577(3) -0.2065(3) 0.1504(2) 0.0728(11) Uani 1 1 d .
C11 C 0.1722(3) -0.2158(3) 0.2176(3) 0.0906(15) Uani 1 1 d .
H11 H 0.1495 -0.2788 0.2356 0.109 Uiso 1 1 calc R
C12 C 0.2198(4) -0.1332(4) 0.2579(2) 0.0955(15) Uani 1 1 d .
H12 H 0.2291 -0.1392 0.3036 0.115 Uiso 1 1 calc R
C13 C 0.2543(3) -0.0404(3) 0.23137(19) 0.0732(10) Uani 1 1 d .
H13 H 0.2883 0.0154 0.2593 0.088 Uiso 1 1 calc R
C14 C 0.1731(4) -0.0999(4) 0.0473(2) 0.1032(15) Uani 1 1 d .
H14A H 0.1595 -0.0215 0.0351 0.155 Uiso 1 1 calc R
H14B H 0.1214 -0.1470 0.0251 0.155 Uiso 1 1 calc R
H14C H 0.2282 -0.1232 0.0347 0.155 Uiso 1 1 calc R
C15 C 0.35930(17) 0.0078(2) -0.07285(13) 0.0390(6) Uani 1 1 d .
C16 C 0.25490(17) 0.0139(2) -0.10097(13) 0.0376(5) Uani 1 1 d .
C17 C 0.2120(2) 0.1188(2) -0.09989(16) 0.0500(7) Uani 1 1 d .
H17 H 0.2489 0.1827 -0.0849 0.060 Uiso 1 1 calc R
C18 C 0.1163(2) 0.1314(3) -0.12044(19) 0.0641(9) Uani 1 1 d .
H18 H 0.0887 0.2021 -0.1179 0.077 Uiso 1 1 calc R
C19 C 0.0620(2) 0.0372(3) -0.14483(19) 0.0630(9) Uani 1 1 d .
H19 H -0.0025 0.0451 -0.1594 0.076 Uiso 1 1 calc R
C20 C 0.10202(18) -0.0676(2) -0.14783(16) 0.0497(7) Uani 1 1 d .
H20 H 0.0643 -0.1298 -0.1649 0.060 Uiso 1 1 calc R
C21 C 0.19903(17) -0.0825(2) -0.12547(13) 0.0406(6) Uani 1 1 d .
C22 C 0.18704(19) -0.2931(2) -0.13598(18) 0.0561(8) Uani 1 1 d .
C23 C 0.1559(2) -0.3455(3) -0.19715(17) 0.0584(8) Uani 1 1 d .
C24 C 0.1104(3) -0.4490(3) -0.19926(19) 0.0671(9) Uani 1 1 d .
C25 C 0.0929(3) -0.5009(3) -0.1453(3) 0.0810(12) Uani 1 1 d .
H25 H 0.0601 -0.5695 -0.1493 0.097 Uiso 1 1 calc R
C26 C 0.1257(3) -0.4478(4) -0.0839(2) 0.0855(13) Uani 1 1 d .
H26 H 0.1162 -0.4820 -0.0459 0.103 Uiso 1 1 calc R
C27 C 0.1718(2) -0.3459(4) -0.07899(19) 0.0720(10) Uani 1 1 d .
H27 H 0.1933 -0.3111 -0.0377 0.086 Uiso 1 1 calc R
C28 C 0.1741(3) -0.2946(4) -0.2588(2) 0.0916(13) Uani 1 1 d .
H28A H 0.1904 -0.3543 -0.2854 0.137 Uiso 1 1 calc R
H28B H 0.2247 -0.2409 -0.2466 0.137 Uiso 1 1 calc R
H28C H 0.1190 -0.2561 -0.2837 0.137 Uiso 1 1 calc R
C29 C 0.5664(2) 0.3190(3) 0.14436(16) 0.0588(8) Uani 1 1 d .
H29 H 0.5436 0.2502 0.1561 0.071 Uiso 1 1 calc R
C30 C 0.5972(3) 0.3976(3) 0.19258(19) 0.0760(11) Uani 1 1 d .
H30 H 0.5951 0.3836 0.2361 0.091 Uiso 1 1 calc R
C31 C 0.6318(3) 0.4996(3) 0.1751(2) 0.0813(12) Uani 1 1 d .
H31 H 0.6540 0.5551 0.2072 0.098 Uiso 1 1 calc R
C32 C 0.6335(2) 0.5188(3) 0.11141(19) 0.0634(9) Uani 1 1 d .
H32 H 0.6559 0.5874 0.0991 0.076 Uiso 1 1 calc R
C33 C 0.60050(18) 0.4327(2) 0.06427(15) 0.0436(6) Uani 1 1 d .
C34 C 0.59596(18) 0.3851(2) -0.05502(15) 0.0448(6) Uani 1 1 d .
C35 C 0.6237(2) 0.4320(3) -0.10865(18) 0.0648(9) Uani 1 1 d .
H35 H 0.6447 0.5071 -0.1069 0.078 Uiso 1 1 calc R
C36 C 0.6197(3) 0.3667(3) -0.1634(2) 0.0746(10) Uani 1 1 d .
H36 H 0.6375 0.3971 -0.1995 0.089 Uiso 1 1 calc R
C37 C 0.5892(3) 0.2552(3) -0.16500(19) 0.0718(10) Uani 1 1 d .
H37 H 0.5877 0.2085 -0.2014 0.086 Uiso 1 1 calc R
C38 C 0.5611(2) 0.2151(3) -0.11152(17) 0.0599(8) Uani 1 1 d .
H38 H 0.5398 0.1401 -0.1128 0.072 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'
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'
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'
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
O4 Mn1 O3 108.15(8) 3_655 .
O4 Mn1 O1 99.50(9) 3_655 .
O3 Mn1 O1 88.35(8) . .
O4 Mn1 N4 96.14(9) 3_655 .
O3 Mn1 N4 91.68(8) . .
O1 Mn1 N4 163.53(8) . .
O4 Mn1 N3 86.16(8) 3_655 .
O3 Mn1 N3 164.50(8) . .
O1 Mn1 N3 95.23(8) . .
N4 Mn1 N3 80.63(8) . .
O4 Mn1 O2 152.03(9) 3_655 .
O3 Mn1 O2 87.92(7) . .
O1 Mn1 O2 57.16(7) . .
N4 Mn1 O2 106.37(7) . .
N3 Mn1 O2 81.46(8) . .
O4 Mn1 C1 127.18(9) 3_655 .
O3 Mn1 C1 86.25(8) . .
O1 Mn1 C1 28.60(8) . .
N4 Mn1 C1 134.97(8) . .
N3 Mn1 C1 89.71(8) . .
O2 Mn1 C1 28.65(7) . .
C7 N1 C8 122.6(2) . .
C7 N1 H1 118.7 . .
C8 N1 H1 118.7 . .
C21 N2 C22 124.4(2) . .
C21 N2 H2 117.8 . .
C22 N2 H2 117.8 . .
C33 N3 C29 117.4(3) . .
C33 N3 Mn1 129.3(2) . .
C29 N3 Mn1 112.83(19) . .
C34 N4 C38 117.4(2) . .
C34 N4 Mn1 129.11(19) . .
C38 N4 Mn1 113.14(19) . .
C34 N5 C33 133.0(2) . .
C34 N5 H5 113.5 . .
C33 N5 H5 113.5 . .
C1 O1 Mn1 94.57(16) . .
C1 O2 Mn1 87.82(15) . .
C15 O3 Mn1 139.28(19) . .
C15 O4 Mn1 150.37(18) . 3_655
O2 C1 O1 120.1(2) . .
O2 C1 C2 119.7(2) . .
O1 C1 C2 120.2(2) . .
O2 C1 Mn1 63.53(14) . .
O1 C1 Mn1 56.83(13) . .
C2 C1 Mn1 173.32(19) . .
C3 C2 C7 119.3(2) . .
C3 C2 C1 118.0(2) . .
C7 C2 C1 122.6(2) . .
C4 C3 C2 121.7(3) . .
C4 C3 H3 119.2 . .
C2 C3 H3 119.2 . .
C5 C4 C3 119.3(3) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 C6 120.6(3) . .
C4 C5 H5A 119.7 . .
C6 C5 H5A 119.7 . .
C5 C6 C7 121.2(3) . .
C5 C6 H6 119.4 . .
C7 C6 H6 119.4 . .
N1 C7 C6 120.3(3) . .
N1 C7 C2 121.8(2) . .
C6 C7 C2 117.9(3) . .
C13 C8 C9 121.4(3) . .
C13 C8 N1 118.8(3) . .
C9 C8 N1 119.8(3) . .
C8 C9 C10 116.1(3) . .
C8 C9 C14 120.7(3) . .
C10 C9 C14 123.2(4) . .
C11 C10 C9 122.3(4) . .
C11 C10 Cl1 118.2(3) . .
C9 C10 Cl1 119.5(3) . .
C12 C11 C10 119.9(3) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C13 120.2(4) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C8 C13 C12 120.1(4) . .
C8 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C9 C14 H14A 109.5 . .
C9 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C9 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O3 C15 O4 123.9(2) . .
O3 C15 C16 118.6(2) . .
O4 C15 C16 117.5(2) . .
C17 C16 C21 119.0(2) . .
C17 C16 C15 117.7(2) . .
C21 C16 C15 123.3(2) . .
C18 C17 C16 121.9(3) . .
C18 C17 H17 119.1 . .
C16 C17 H17 119.1 . .
C17 C18 C19 118.9(3) . .
C17 C18 H18 120.5 . .
C19 C18 H18 120.5 . .
C20 C19 C18 120.9(3) . .
C20 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
C19 C20 C21 120.9(3) . .
C19 C20 H20 119.6 . .
C21 C20 H20 119.6 . .
N2 C21 C20 120.1(2) . .
N2 C21 C16 121.6(2) . .
C20 C21 C16 118.4(2) . .
C23 C22 C27 119.7(3) . .
C23 C22 N2 121.9(3) . .
C27 C22 N2 118.3(3) . .
C24 C23 C22 117.5(3) . .
C24 C23 C28 121.0(3) . .
C22 C23 C28 121.5(3) . .
C25 C24 C23 124.1(4) . .
C25 C24 Cl2 116.5(3) . .
C23 C24 Cl2 119.3(3) . .
C24 C25 C26 117.7(4) . .
C24 C25 H25 121.2 . .
C26 C25 H25 121.2 . .
C27 C26 C25 120.5(4) . .
C27 C26 H26 119.7 . .
C25 C26 H26 119.7 . .
C26 C27 C22 120.4(4) . .
C26 C27 H27 119.8 . .
C22 C27 H27 119.8 . .
C23 C28 H28A 109.5 . .
C23 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C23 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
N3 C29 C30 124.1(3) . .
N3 C29 H29 118.0 . .
C30 C29 H29 118.0 . .
C29 C30 C31 117.8(4) . .
C29 C30 H30 121.1 . .
C31 C30 H30 121.1 . .
C32 C31 C30 120.2(3) . .
C32 C31 H31 119.9 . .
C30 C31 H31 119.9 . .
C31 C32 C33 118.5(3) . .
C31 C32 H32 120.8 . .
C33 C32 H32 120.8 . .
N3 C33 N5 120.7(2) . .
N3 C33 C32 122.0(3) . .
N5 C33 C32 117.3(3) . .
N4 C34 N5 121.5(2) . .
N4 C34 C35 121.7(3) . .
N5 C34 C35 116.8(3) . .
C36 C35 C34 119.5(3) . .
C36 C35 H35 120.3 . .
C34 C35 H35 120.3 . .
C35 C36 C37 119.7(3) . .
C35 C36 H36 120.2 . .
C37 C36 H36 120.2 . .
C38 C37 C36 118.1(3) . .
C38 C37 H37 121.0 . .
C36 C37 H37 121.0 . .
N4 C38 C37 123.7(3) . .
N4 C38 H38 118.1 . .
C37 C38 H38 118.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O4 2.087(2) 3_655
Mn1 O3 2.1023(19) .
Mn1 O1 2.2152(19) .
Mn1 N4 2.245(2) .
Mn1 N3 2.266(2) .
Mn1 O2 2.3632(19) .
Mn1 C1 2.638(3) .
Cl1 C10 1.732(4) .
Cl2 C24 1.749(4) .
N1 C7 1.368(4) .
N1 C8 1.424(4) .
N1 H1 0.8600 .
N2 C21 1.379(3) .
N2 C22 1.419(4) .
N2 H2 0.8600 .
N3 C33 1.333(3) .
N3 C29 1.348(4) .
N4 C34 1.337(3) .
N4 C38 1.355(4) .
N5 C34 1.375(4) .
N5 C33 1.386(4) .
N5 H5 0.8600 .
O1 C1 1.267(3) .
O2 C1 1.266(3) .
O3 C15 1.242(3) .
O4 C15 1.252(3) .
O4 Mn1 2.087(2) 3_655
C1 C2 1.488(4) .
C2 C3 1.384(4) .
C2 C7 1.408(4) .
C3 C4 1.375(4) .
C3 H3 0.9300 .
C4 C5 1.370(5) .
C4 H4 0.9300 .
C5 C6 1.373(5) .
C5 H5A 0.9300 .
C6 C7 1.401(4) .
C6 H6 0.9300 .
C8 C13 1.373(5) .
C8 C9 1.392(5) .
C9 C10 1.398(5) .
C9 C14 1.493(5) .
C10 C11 1.367(6) .
C11 C12 1.352(7) .
C11 H11 0.9300 .
C12 C13 1.376(5) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 C16 1.507(3) .
C16 C17 1.384(4) .
C16 C21 1.414(3) .
C17 C18 1.379(4) .
C17 H17 0.9300 .
C18 C19 1.380(4) .
C18 H18 0.9300 .
C19 C20 1.370(4) .
C19 H19 0.9300 .
C20 C21 1.402(4) .
C20 H20 0.9300 .
C22 C23 1.383(5) .
C22 C27 1.408(5) .
C23 C24 1.381(4) .
C23 C28 1.503(5) .
C24 C25 1.361(6) .
C25 C26 1.393(6) .
C25 H25 0.9300 .
C26 C27 1.364(6) .
C26 H26 0.9300 .
C27 H27 0.9300 .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C29 C30 1.351(5) .
C29 H29 0.9300 .
C30 C31 1.384(5) .
C30 H30 0.9300 .
C31 C32 1.353(5) .
C31 H31 0.9300 .
C32 C33 1.403(4) .
C32 H32 0.9300 .
C34 C35 1.399(4) .
C35 C36 1.362(5) .
C35 H35 0.9300 .
C36 C37 1.378(5) .
C36 H36 0.9300 .
C37 C38 1.369(5) .
C37 H37 0.9300 .
C38 H38 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.03 2.650(3) 128.3 .
N2 H2 O4 0.86 2.10 2.665(3) 123.0 .
N5 H5 O2 0.86 2.03 2.886(3) 173.8 3_665
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
O4 Mn1 N3 C33 116.9(2) 3_655
O3 Mn1 N3 C33 -41.0(4) .
O1 Mn1 N3 C33 -143.9(2) .
N4 Mn1 N3 C33 20.1(2) .
O2 Mn1 N3 C33 -88.2(2) .
C1 Mn1 N3 C33 -115.8(2) .
O4 Mn1 N3 C29 -71.0(2) 3_655
O3 Mn1 N3 C29 131.0(3) .
O1 Mn1 N3 C29 28.2(2) .
N4 Mn1 N3 C29 -167.9(2) .
O2 Mn1 N3 C29 83.8(2) .
C1 Mn1 N3 C29 56.3(2) .
O4 Mn1 N4 C34 -105.9(2) 3_655
O3 Mn1 N4 C34 145.7(2) .
O1 Mn1 N4 C34 55.8(4) .
N3 Mn1 N4 C34 -20.8(2) .
O2 Mn1 N4 C34 57.3(2) .
C1 Mn1 N4 C34 59.3(3) .
O4 Mn1 N4 C38 81.5(2) 3_655
O3 Mn1 N4 C38 -26.9(2) .
O1 Mn1 N4 C38 -116.8(3) .
N3 Mn1 N4 C38 166.6(2) .
O2 Mn1 N4 C38 -115.3(2) .
C1 Mn1 N4 C38 -113.3(2) .
O4 Mn1 O1 C1 166.69(17) 3_655
O3 Mn1 O1 C1 -85.18(17) .
N4 Mn1 O1 C1 5.2(4) .
N3 Mn1 O1 C1 79.72(17) .
O2 Mn1 O1 C1 3.41(15) .
O4 Mn1 O2 C1 -40.6(2) 3_655
O3 Mn1 O2 C1 85.98(16) .
O1 Mn1 O2 C1 -3.40(15) .
N4 Mn1 O2 C1 177.12(16) .
N3 Mn1 O2 C1 -105.33(16) .
O4 Mn1 O3 C15 58.7(3) 3_655
O1 Mn1 O3 C15 -40.8(3) .
N4 Mn1 O3 C15 155.7(3) .
N3 Mn1 O3 C15 -144.5(3) .
O2 Mn1 O3 C15 -97.9(3) .
C1 Mn1 O3 C15 -69.3(3) .
Mn1 O2 C1 O1 5.8(3) .
Mn1 O2 C1 C2 -173.4(2) .
Mn1 O1 C1 O2 -6.2(3) .
Mn1 O1 C1 C2 173.0(2) .
O4 Mn1 C1 O2 157.46(14) 3_655
O3 Mn1 C1 O2 -92.53(16) .
O1 Mn1 C1 O2 174.0(3) .
N4 Mn1 C1 O2 -3.9(2) .
N3 Mn1 C1 O2 72.50(16) .
O4 Mn1 C1 O1 -16.6(2) 3_655
O3 Mn1 C1 O1 93.45(17) .
N4 Mn1 C1 O1 -177.92(16) .
N3 Mn1 C1 O1 -101.52(17) .
O2 Mn1 C1 O1 -174.0(3) .
O2 C1 C2 C3 -2.0(4) .
O1 C1 C2 C3 178.9(3) .
O2 C1 C2 C7 176.1(3) .
O1 C1 C2 C7 -3.1(4) .
C7 C2 C3 C4 1.4(6) .
C1 C2 C3 C4 179.4(4) .
C2 C3 C4 C5 -2.2(7) .
C3 C4 C5 C6 1.5(8) .
C4 C5 C6 C7 -0.1(8) .
C8 N1 C7 C6 16.5(5) .
C8 N1 C7 C2 -164.7(3) .
C5 C6 C7 N1 178.2(4) .
C5 C6 C7 C2 -0.7(6) .
C3 C2 C7 N1 -178.7(3) .
C1 C2 C7 N1 3.3(5) .
C3 C2 C7 C6 0.1(5) .
C1 C2 C7 C6 -177.9(3) .
C7 N1 C8 C13 -101.0(4) .
C7 N1 C8 C9 79.2(4) .
C13 C8 C9 C10 -1.1(5) .
N1 C8 C9 C10 178.8(3) .
C13 C8 C9 C14 -179.7(4) .
N1 C8 C9 C14 0.1(5) .
C8 C9 C10 C11 2.0(5) .
C14 C9 C10 C11 -179.4(4) .
C8 C9 C10 Cl1 -176.8(2) .
C14 C9 C10 Cl1 1.8(5) .
C9 C10 C11 C12 -1.2(6) .
Cl1 C10 C11 C12 177.6(3) .
C10 C11 C12 C13 -0.6(7) .
C9 C8 C13 C12 -0.7(5) .
N1 C8 C13 C12 179.5(3) .
C11 C12 C13 C8 1.6(7) .
Mn1 O3 C15 O4 -61.3(4) .
Mn1 O3 C15 C16 118.7(3) .
Mn1 O4 C15 O3 13.7(6) 3_655
Mn1 O4 C15 C16 -166.3(3) 3_655
O3 C15 C16 C17 -16.4(4) .
O4 C15 C16 C17 163.6(3) .
O3 C15 C16 C21 166.4(2) .
O4 C15 C16 C21 -13.6(4) .
C21 C16 C17 C18 1.7(5) .
C15 C16 C17 C18 -175.7(3) .
C16 C17 C18 C19 -2.2(5) .
C17 C18 C19 C20 1.0(6) .
C18 C19 C20 C21 0.8(5) .
C22 N2 C21 C20 -16.8(5) .
C22 N2 C21 C16 163.6(3) .
C19 C20 C21 N2 179.1(3) .
C19 C20 C21 C16 -1.3(4) .
C17 C16 C21 N2 179.6(3) .
C15 C16 C21 N2 -3.1(4) .
C17 C16 C21 C20 0.1(4) .
C15 C16 C21 C20 177.3(2) .
C21 N2 C22 C23 97.8(4) .
C21 N2 C22 C27 -84.9(4) .
C27 C22 C23 C24 0.1(5) .
N2 C22 C23 C24 177.4(3) .
C27 C22 C23 C28 -177.4(3) .
N2 C22 C23 C28 -0.2(5) .
C22 C23 C24 C25 1.4(5) .
C28 C23 C24 C25 178.9(4) .
C22 C23 C24 Cl2 179.0(3) .
C28 C23 C24 Cl2 -3.4(5) .
C23 C24 C25 C26 -2.2(6) .
Cl2 C24 C25 C26 -179.9(3) .
C24 C25 C26 C27 1.5(6) .
C25 C26 C27 C22 -0.2(5) .
C23 C22 C27 C26 -0.7(5) .
N2 C22 C27 C26 -178.0(3) .
C33 N3 C29 C30 0.7(5) .
Mn1 N3 C29 C30 -172.4(3) .
N3 C29 C30 C31 -0.5(6) .
C29 C30 C31 C32 0.6(6) .
C30 C31 C32 C33 -0.8(6) .
C29 N3 C33 N5 179.5(3) .
Mn1 N3 C33 N5 -8.8(4) .
C29 N3 C33 C32 -0.9(4) .
Mn1 N3 C33 C32 170.8(2) .
C34 N5 C33 N3 -15.4(4) .
C34 N5 C33 C32 164.9(3) .
C31 C32 C33 N3 1.0(5) .
C31 C32 C33 N5 -179.4(3) .
C38 N4 C34 N5 -177.2(3) .
Mn1 N4 C34 N5 10.4(4) .
C38 N4 C34 C35 3.4(4) .
Mn1 N4 C34 C35 -168.9(2) .
C33 N5 C34 N4 14.7(4) .
C33 N5 C34 C35 -166.0(3) .
N4 C34 C35 C36 -2.3(5) .
N5 C34 C35 C36 178.4(3) .
C34 C35 C36 C37 -0.5(6) .
C35 C36 C37 C38 1.9(6) .
C34 N4 C38 C37 -2.0(5) .
Mn1 N4 C38 C37 171.6(3) .
C36 C37 C38 N4 -0.7(6) .
