#------------------------------------------------------------------------------
#$Date: 2016-02-17 16:13:21 +0200 (Wed, 17 Feb 2016) $
#$Revision: 176652 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/14/2241446.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2241446
loop_
_publ_author_name
'An, Zhe'
'Gao, Jing'
'Harrison, William T. A.'
_publ_section_title
;
 Crystal structures of [Mn(bdc)(Hspar)₂(H₂O)~0.25~]·2H₂O
 containing MnO₆₊₁ capped trigonal prisms and
 [Cu(Hspar)₂](bdc)·2H₂O containing CuO₄ squares (Hspar =
 sparfloxacin and bdc = benzene-1,4-dicarboxylate)
;
_journal_coeditor_code           SJ5492
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              96
_journal_page_last               101
_journal_paper_doi               10.1107/S205698901502424X
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac
'[Mn (C8 H4 O4) (C19 H22 F2 N4 O3)2 (H2 O)0.25], 2H2 O'
_chemical_formula_moiety         'C46 H48.50 F4 Mn N8 O10.25, 2(H2 O)'
_chemical_formula_sum            'C46 H52.5 F4 Mn N8 O12.25'
_chemical_formula_weight         1044.40
_chemical_name_systematic
'0.25-Aqua(benzene-1,4-dicarboxylato-κ²O,O')bis(sparfloxacin-κ²O,O')manganese(II) dihydrate'
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.7250(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1128(7)
_cell_length_b                   20.8621(12)
_cell_length_c                   17.6284(10)
_cell_measurement_reflns_used    3519
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.83
_cell_measurement_theta_min      2.41
_cell_volume                     4618.4(4)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
SMART (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0816
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43573
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  0.9457
_exptl_absorpt_correction_T_min  0.9286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2174
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         10603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0592
_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)+(0.0624P)²+0.3922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1548
_reflns_number_gt                5832
_reflns_number_total             10603
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5492sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
;Adding full bibliography for 2241446--2241447.cif.

 Adding full bibliography for 2241446--2241447.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C46 H52.50 F4 Mn N8 O12.25'
_cod_database_code               2241446
_cod_database_fobs_code          2241446
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Mn Mn1 0.24557(4) 0.50546(2) -0.08355(3) 0.03353(14) Uani d . 1 1
C C1 0.3662(3) 0.37777(17) -0.0926(2) 0.0436(8) Uani d . 1 1
C C2 0.3073(2) 0.34168(14) -0.04545(17) 0.0343(7) Uani d . 1 1
C C3 0.2279(2) 0.36801(15) -0.01256(16) 0.0328(7) Uani d . 1 1
C C4 0.1766(2) 0.32345(14) 0.02819(17) 0.0341(7) Uani d . 1 1
C C5 0.0966(2) 0.34353(16) 0.06350(18) 0.0388(8) Uani d . 1 1
C C6 0.0445(3) 0.29665(18) 0.0930(2) 0.0488(9) Uani d . 1 1
C C7 0.0655(3) 0.23150(18) 0.0926(2) 0.0530(10) Uani d . 1 1
C C8 0.1433(3) 0.21331(16) 0.0586(2) 0.0497(9) Uani d . 1 1
C C9 0.2041(2) 0.25707(15) 0.03201(18) 0.0380(8) Uani d . 1 1
C C10 0.3369(2) 0.27935(15) -0.02990(18) 0.0391(8) Uani d . 1 1
H H10 0.3935 0.2647 -0.0470 0.047 Uiso calc R 1 1
C C11 0.3414(3) 0.17419(15) 0.0295(2) 0.0467(9) Uani d . 1 1
H H11 0.3110 0.1386 -0.0061 0.056 Uiso calc R 1 1
C C12 0.3858(3) 0.15806(17) 0.1143(2) 0.0547(10) Uani d . 1 1
H H12A 0.3813 0.1138 0.1299 0.066 Uiso calc R 1 1
H H12B 0.3788 0.1896 0.1529 0.066 Uiso calc R 1 1
C C13 0.4591(3) 0.17312(19) 0.0659(2) 0.0644(11) Uani d . 1 1
H H13A 0.4988 0.1380 0.0520 0.077 Uiso calc R 1 1
H H13B 0.4963 0.2139 0.0750 0.077 Uiso calc R 1 1
C C14 -0.0986(3) 0.1819(2) 0.1131(2) 0.0652(11) Uani d . 1 1
H H14A -0.1236 0.1457 0.0781 0.078 Uiso calc R 1 1
H H14B -0.1331 0.2202 0.0867 0.078 Uiso calc R 1 1
C C15 -0.1268(3) 0.1725(2) 0.1865(2) 0.0589(10) Uani d . 1 1
H H15 -0.1085 0.2120 0.2175 0.071 Uiso calc R 1 1
C C16 0.0533(3) 0.12232(19) 0.2441(2) 0.0574(10) Uani d . 1 1
H H16 0.0815 0.1602 0.2763 0.069 Uiso calc R 1 1
C C17 0.0725(3) 0.1306(2) 0.1677(3) 0.0833(15) Uani d . 1 1
H H17A 0.0476 0.0932 0.1349 0.100 Uiso calc R 1 1
H H17B 0.1483 0.1353 0.1747 0.100 Uiso calc R 1 1
C C18 -0.2450(3) 0.1593(2) 0.1752(3) 0.0715(12) Uani d . 1 1
H H18A -0.2859 0.1964 0.1527 0.107 Uiso calc R 1 1
H H18B -0.2560 0.1499 0.2256 0.107 Uiso calc R 1 1
H H18C -0.2673 0.1234 0.1403 0.107 Uiso calc R 1 1
C C19 0.1081(3) 0.06386(17) 0.2888(2) 0.0610(11) Uani d . 1 1
H H19A 0.0833 0.0261 0.2579 0.091 Uiso calc R 1 1
H H19B 0.0922 0.0607 0.3385 0.091 Uiso calc R 1 1
H H19C 0.1837 0.0678 0.2982 0.091 Uiso calc R 1 1
N N1 0.0748(2) 0.40641(14) 0.07178(16) 0.0518(8) Uani d . 1 1
H H1A 0.0284 0.4170 0.0955 0.062 Uiso calc R 1 1
H H1B 0.1074 0.4356 0.0533 0.062 Uiso calc R 1 1
N N2 0.2918(2) 0.23737(12) 0.00780(15) 0.0383(6) Uani d . 1 1
N N3 0.0158(2) 0.18803(16) 0.1292(2) 0.0799(12) Uani d . 1 1
N N4 -0.0632(2) 0.11872(13) 0.23537(16) 0.0450(7) Uani d . 1 1
H H4A -0.0731 0.1195 0.2838 0.054 Uiso calc R 1 1
H H4B -0.0884 0.0811 0.2126 0.054 Uiso calc R 1 1
O O1 0.4253(2) 0.34607(12) -0.12306(16) 0.0638(7) Uani d . 1 1
O O2 0.3552(2) 0.43743(11) -0.10042(16) 0.0626(7) Uani d . 1 1
O O3 0.20213(16) 0.42675(10) -0.01847(12) 0.0388(5) Uani d . 1 1
F F1 -0.02880(15) 0.31754(10) 0.12892(12) 0.0642(6) Uani d . 1 1
F F2 0.15513(17) 0.14946(10) 0.04660(15) 0.0718(7) Uani d . 1 1
C C20 0.3488(3) 0.64075(16) -0.07543(19) 0.0410(8) Uani d . 1 1
C C21 0.3025(2) 0.66361(14) -0.01229(17) 0.0327(7) Uani d . 1 1
C C22 0.2345(2) 0.62688(14) 0.02221(16) 0.0304(7) Uani d . 1 1
C C23 0.1873(2) 0.66087(14) 0.07591(16) 0.0306(7) Uani d . 1 1
C C24 0.1099(2) 0.63154(14) 0.10809(17) 0.0330(7) Uani d . 1 1
C C25 0.0609(2) 0.66937(16) 0.15148(19) 0.0391(8) Uani d . 1 1
C C26 0.0803(2) 0.73363(16) 0.1662(2) 0.0418(8) Uani d . 1 1
C C27 0.1566(3) 0.76117(15) 0.1359(2) 0.0421(8) Uani d . 1 1
C C28 0.2130(2) 0.72662(15) 0.09484(18) 0.0340(7) Uani d . 1 1
C C29 0.3311(2) 0.72359(15) 0.01592(18) 0.0366(7) Uani d . 1 1
H H29 0.3808 0.7449 -0.0033 0.044 Uiso calc R 1 1
C C30 0.3460(3) 0.81431(15) 0.1034(2) 0.0458(9) Uani d . 1 1
H H30 0.3127 0.8543 0.0793 0.055 Uiso calc R 1 1
C C31 0.3993(3) 0.81582(18) 0.1898(2) 0.0588(10) Uani d . 1 1
H H31A 0.3964 0.7774 0.2201 0.071 Uiso calc R 1 1
H H31B 0.3976 0.8557 0.2177 0.071 Uiso calc R 1 1
C C32 0.4648(3) 0.81376(19) 0.1328(3) 0.0674(12) Uani d . 1 1
H H32A 0.5023 0.8524 0.1261 0.081 Uiso calc R 1 1
H H32B 0.5012 0.7740 0.1285 0.081 Uiso calc R 1 1
C C33 -0.0843(2) 0.76537(17) 0.2025(2) 0.0481(9) Uani d . 1 1
H H33A -0.0922 0.7443 0.2495 0.058 Uiso calc R 1 1
H H33B -0.1194 0.7394 0.1568 0.058 Uiso calc R 1 1
C C34 -0.1347(2) 0.83148(17) 0.19441(19) 0.0437(8) Uani d . 1 1
H H34 -0.1318 0.8506 0.1443 0.052 Uiso calc R 1 1
C C35 0.0423(2) 0.87778(15) 0.27129(18) 0.0380(8) Uani d . 1 1
H H35 0.0548 0.9011 0.2266 0.046 Uiso calc R 1 1
C C36 0.0863(2) 0.81119(15) 0.2745(2) 0.0439(8) Uani d . 1 1
H H36A 0.1603 0.8135 0.2747 0.053 Uiso calc R 1 1
H H36B 0.0840 0.7909 0.3235 0.053 Uiso calc R 1 1
C C37 -0.2504(3) 0.8294(2) 0.1959(2) 0.0652(11) Uani d . 1 1
H H37A -0.2536 0.8123 0.2457 0.098 Uiso calc R 1 1
H H37B -0.2908 0.8025 0.1537 0.098 Uiso calc R 1 1
H H37C -0.2794 0.8719 0.1892 0.098 Uiso calc R 1 1
C C38 0.0920(3) 0.91361(16) 0.3473(2) 0.0535(10) Uani d . 1 1
H H38A 0.0518 0.9518 0.3487 0.080 Uiso calc R 1 1
H H38B 0.1639 0.9250 0.3500 0.080 Uiso calc R 1 1
H H38C 0.0921 0.8868 0.3916 0.080 Uiso calc R 1 1
N N5 0.0885(2) 0.56800(12) 0.10051(15) 0.0446(7) Uani d . 1 1
H H5A 0.0444 0.5513 0.1227 0.053 Uiso calc R 1 1
H H5B 0.1189 0.5444 0.0735 0.053 Uiso calc R 1 1
N N6 0.2939(2) 0.75471(11) 0.06912(15) 0.0360(6) Uani d . 1 1
N N7 0.0278(2) 0.77193(14) 0.20811(18) 0.0532(8) Uani d . 1 1
N N8 -0.07495(19) 0.87282(12) 0.26085(14) 0.0377(6) Uani d . 1 1
H H8A -0.0846 0.8576 0.3060 0.045 Uiso calc R 1 1
H H8B -0.1030 0.9125 0.2533 0.045 Uiso calc R 1 1
O O4 0.4009(2) 0.68048(11) -0.10270(14) 0.0559(7) Uani d . 1 1
O O5 0.3336(2) 0.58419(12) -0.10073(15) 0.0627(8) Uani d . 1 1
O O6 0.21452(16) 0.56810(10) 0.00687(12) 0.0382(5) Uani d . 1 1
F F3 -0.00977(15) 0.63937(9) 0.18330(11) 0.0524(5) Uani d . 1 1
F F4 0.16868(16) 0.82596(9) 0.14286(13) 0.0595(6) Uani d . 1 1
C C39 -0.0089(2) 0.50896(15) -0.28773(18) 0.0386(8) Uani d . 1 1
C C40 -0.1129(3) 0.51354(16) -0.28443(19) 0.0417(8) Uani d . 1 1
H H40 -0.1266 0.5163 -0.2356 0.050 Uiso calc R 1 1
C C41 -0.1973(3) 0.51408(16) -0.35408(19) 0.0433(8) Uani d . 1 1
H H41 -0.2669 0.5175 -0.3513 0.052 Uiso calc R 1 1
C C42 -0.1783(3) 0.50961(15) -0.42676(18) 0.0396(8) Uani d . 1 1
C C43 -0.0744(3) 0.50486(19) -0.4288(2) 0.0557(10) Uani d . 1 1
H H43 -0.0608 0.5012 -0.4776 0.067 Uiso calc R 1 1
C C44 0.0102(3) 0.50530(18) -0.3607(2) 0.0544(10) Uani d . 1 1
H H44 0.0797 0.5032 -0.3640 0.065 Uiso calc R 1 1
C C45 0.0824(3) 0.50855(15) -0.21292(19) 0.0383(8) Uani d . 1 1
C C46 -0.2660(3) 0.50852(18) -0.5041(2) 0.0501(9) Uani d . 1 1
O O7 0.17498(19) 0.50044(13) -0.21779(14) 0.0646(8) Uani d . 1 1
O O8 0.06601(16) 0.51510(10) -0.14685(12) 0.0407(5) Uani d . 1 1
O O9 -0.2441(2) 0.48093(17) -0.56076(15) 0.0837(10) Uani d . 1 1
O O10 -0.3529(2) 0.53337(14) -0.50676(15) 0.0693(8) Uani d . 1 1
O O11 0.65934(16) 0.49527(10) 0.28884(12) 0.0432(6) Uani d . 1 1
H H1W 0.6939 0.4892 0.3369 0.052 Uiso d R 1 1
H H2W 0.7131 0.4987 0.2717 0.052 Uiso d R 1 1
O O12 0.4787(2) 0.45928(17) 0.39436(16) 0.0930(10) Uani d . 1 1
H H3W 0.4443 0.4509 0.4274 0.112 Uiso d R 1 1
H H4W 0.5267 0.4809 0.4268 0.112 Uiso d R 1 1
O O13 0.4286(9) 0.5077(5) 0.0220(7) 0.076(3) Uiso d P 0.25 1
H H5W 0.4567 0.5407 0.0593 0.091 Uiso d PR 0.25 1
H H6W 0.5000 0.5000 0.0000 0.091 Uiso d SPR 0.50 2
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'
F F 0.0171 0.0103 '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_publ_flag
O5 Mn1 O2 94.69(10) y
O5 Mn1 O3 156.29(10) y
O2 Mn1 O3 81.86(8) y
O5 Mn1 O6 82.05(8) y
O2 Mn1 O6 141.70(10) y
O3 Mn1 O6 86.26(8) y
O5 Mn1 O7 87.81(10) y
O2 Mn1 O7 84.96(10) y
O3 Mn1 O7 115.05(9) y
O6 Mn1 O7 132.68(9) y
O5 Mn1 O8 113.13(10) y
O2 Mn1 O8 129.45(10) y
O3 Mn1 O8 86.27(8) y
O6 Mn1 O8 85.54(8) y
O7 Mn1 O8 56.58(8) y
O1 C1 O2 122.8(3) ?
O1 C1 C2 117.1(3) ?
O2 C1 C2 120.0(3) ?
C10 C2 C3 118.7(3) ?
C10 C2 C1 115.6(3) ?
C3 C2 C1 125.6(3) ?
O3 C3 C2 122.9(3) ?
O3 C3 C4 120.6(3) ?
C2 C3 C4 116.5(3) ?
C9 C4 C5 118.1(3) ?
C9 C4 C3 119.9(3) ?
C5 C4 C3 122.0(3) ?
N1 C5 C6 120.2(3) ?
N1 C5 C4 122.2(3) ?
C6 C5 C4 117.5(3) ?
F1 C6 C5 116.1(3) ?
F1 C6 C7 118.8(3) ?
C5 C6 C7 125.0(3) ?
C8 C7 N3 122.1(3) ?
C8 C7 C6 116.4(3) ?
N3 C7 C6 121.4(3) ?
F2 C8 C7 117.9(3) ?
F2 C8 C9 119.4(3) ?
C7 C8 C9 122.6(3) ?
C8 C9 N2 121.0(3) ?
C8 C9 C4 119.7(3) ?
N2 C9 C4 119.3(3) ?
N2 C10 C2 125.8(3) ?
N2 C10 H10 117.1 ?
C2 C10 H10 117.1 ?
N2 C11 C12 118.9(3) ?
N2 C11 C13 116.8(3) ?
C12 C11 C13 60.3(2) ?
N2 C11 H11 116.4 ?
C12 C11 H11 116.4 ?
C13 C11 H11 116.4 ?
C11 C12 C13 60.3(2) ?
C11 C12 H12A 117.7 ?
C13 C12 H12A 117.7 ?
C11 C12 H12B 117.7 ?
C13 C12 H12B 117.7 ?
H12A C12 H12B 114.9 ?
C12 C13 C11 59.4(2) ?
C12 C13 H13A 117.8 ?
C11 C13 H13A 117.8 ?
C12 C13 H13B 117.8 ?
C11 C13 H13B 117.8 ?
H13A C13 H13B 115.0 ?
N3 C14 C15 110.5(3) ?
N3 C14 H14A 109.6 ?
C15 C14 H14A 109.6 ?
N3 C14 H14B 109.6 ?
C15 C14 H14B 109.6 ?
H14A C14 H14B 108.1 ?
C14 C15 N4 111.6(3) ?
C14 C15 C18 114.5(3) ?
N4 C15 C18 108.2(3) ?
C14 C15 H15 107.4 ?
N4 C15 H15 107.4 ?
C18 C15 H15 107.4 ?
C17 C16 N4 110.9(3) ?
C17 C16 C19 113.2(3) ?
N4 C16 C19 109.4(3) ?
C17 C16 H16 107.7 ?
N4 C16 H16 107.7 ?
C19 C16 H16 107.7 ?
C16 C17 N3 109.0(4) ?
C16 C17 H17A 109.9 ?
N3 C17 H17A 109.9 ?
C16 C17 H17B 109.9 ?
N3 C17 H17B 109.9 ?
H17A C17 H17B 108.3 ?
C15 C18 H18A 109.5 ?
C15 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C15 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C16 C19 H19A 109.5 ?
C16 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C16 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C5 N1 H1A 120.0 ?
C5 N1 H1B 120.0 ?
H1A N1 H1B 120.0 ?
C10 N2 C9 118.7(3) ?
C10 N2 C11 119.4(3) ?
C9 N2 C11 121.7(3) ?
C7 N3 C14 124.6(3) ?
C7 N3 C17 120.4(3) ?
C14 N3 C17 112.1(3) ?
C16 N4 C15 113.7(3) ?
C16 N4 H4A 108.8 ?
C15 N4 H4A 108.8 ?
C16 N4 H4B 108.8 ?
C15 N4 H4B 108.8 ?
H4A N4 H4B 107.7 ?
C1 O2 Mn1 135.6(2) ?
C3 O3 Mn1 132.10(19) ?
O4 C20 O5 122.2(3) ?
O4 C20 C21 117.3(3) ?
O5 C20 C21 120.5(3) ?
C29 C21 C22 118.4(3) ?
C29 C21 C20 116.0(3) ?
C22 C21 C20 125.5(3) ?
O6 C22 C21 122.8(3) ?
O6 C22 C23 120.6(3) ?
C21 C22 C23 116.6(3) ?
C28 C23 C24 117.6(3) ?
C28 C23 C22 120.2(3) ?
C24 C23 C22 122.1(3) ?
N5 C24 C25 119.9(3) ?
N5 C24 C23 121.9(3) ?
C25 C24 C23 118.1(3) ?
F3 C25 C26 118.7(3) ?
F3 C25 C24 116.4(3) ?
C26 C25 C24 124.8(3) ?
C25 C26 C27 116.5(3) ?
C25 C26 N7 124.3(3) ?
C27 C26 N7 119.1(3) ?
F4 C27 C28 120.0(3) ?
F4 C27 C26 117.0(3) ?
C28 C27 C26 122.8(3) ?
C27 C28 N6 121.6(3) ?
C27 C28 C23 119.9(3) ?
N6 C28 C23 118.5(3) ?
N6 C29 C21 125.7(3) ?
N6 C29 H29 117.2 ?
C21 C29 H29 117.2 ?
N6 C30 C31 118.0(3) ?
N6 C30 C32 117.0(3) ?
C31 C30 C32 60.5(3) ?
N6 C30 H30 116.6 ?
C31 C30 H30 116.6 ?
C32 C30 H30 116.6 ?
C30 C31 C32 60.1(2) ?
C30 C31 H31A 117.8 ?
C32 C31 H31A 117.8 ?
C30 C31 H31B 117.8 ?
C32 C31 H31B 117.8 ?
H31A C31 H31B 114.9 ?
C30 C32 C31 59.4(2) ?
C30 C32 H32A 117.8 ?
C31 C32 H32A 117.8 ?
C30 C32 H32B 117.8 ?
C31 C32 H32B 117.8 ?
H32A C32 H32B 115.0 ?
N7 C33 C34 109.1(3) ?
N7 C33 H33A 109.9 ?
C34 C33 H33A 109.9 ?
N7 C33 H33B 109.9 ?
C34 C33 H33B 109.9 ?
H33A C33 H33B 108.3 ?
N8 C34 C33 109.7(3) ?
N8 C34 C37 107.8(3) ?
C33 C34 C37 112.4(3) ?
N8 C34 H34 109.0 ?
C33 C34 H34 109.0 ?
C37 C34 H34 109.0 ?
N8 C35 C36 108.1(2) ?
N8 C35 C38 108.0(3) ?
C36 C35 C38 111.2(3) ?
N8 C35 H35 109.8 ?
C36 C35 H35 109.8 ?
C38 C35 H35 109.8 ?
N7 C36 C35 112.6(3) ?
N7 C36 H36A 109.1 ?
C35 C36 H36A 109.1 ?
N7 C36 H36B 109.1 ?
C35 C36 H36B 109.1 ?
H36A C36 H36B 107.8 ?
C34 C37 H37A 109.5 ?
C34 C37 H37B 109.5 ?
H37A C37 H37B 109.5 ?
C34 C37 H37C 109.5 ?
H37A C37 H37C 109.5 ?
H37B C37 H37C 109.5 ?
C35 C38 H38A 109.5 ?
C35 C38 H38B 109.5 ?
H38A C38 H38B 109.5 ?
C35 C38 H38C 109.5 ?
H38A C38 H38C 109.5 ?
H38B C38 H38C 109.5 ?
C24 N5 H5A 120.0 ?
C24 N5 H5B 120.0 ?
H5A N5 H5B 120.0 ?
C29 N6 C28 119.1(3) ?
C29 N6 C30 118.6(3) ?
C28 N6 C30 122.0(3) ?
C26 N7 C33 123.6(3) ?
C26 N7 C36 121.4(3) ?
C33 N7 C36 113.5(2) ?
C34 N8 C35 115.3(2) ?
C34 N8 H8A 108.4 ?
C35 N8 H8A 108.4 ?
C34 N8 H8B 108.4 ?
C35 N8 H8B 108.4 ?
H8A N8 H8B 107.5 ?
C20 O5 Mn1 136.7(2) ?
C22 O6 Mn1 131.53(18) ?
C44 C39 C40 119.2(3) ?
C44 C39 C45 120.3(3) ?
C40 C39 C45 120.6(3) ?
C39 C40 C41 120.3(3) ?
C39 C40 H40 119.9 ?
C41 C40 H40 119.9 ?
C42 C41 C40 120.5(3) ?
C42 C41 H41 119.8 ?
C40 C41 H41 119.8 ?
C43 C42 C41 118.3(3) ?
C43 C42 C46 118.5(3) ?
C41 C42 C46 123.1(3) ?
C42 C43 C44 122.1(3) ?
C42 C43 H43 119.0 ?
C44 C43 H43 119.0 ?
C43 C44 C39 119.6(3) ?
C43 C44 H44 120.2 ?
C39 C44 H44 120.2 ?
O8 C45 O7 120.5(3) ?
O8 C45 C39 120.6(3) ?
O7 C45 C39 118.9(3) ?
O10 C46 O9 125.4(3) ?
O10 C46 C42 118.7(3) ?
O9 C46 C42 115.9(3) ?
C45 O7 Mn1 91.98(19) ?
C45 O8 Mn1 90.91(19) ?
H1W O11 H2W 96.2 ?
H3W O12 H4W 94.9 ?
H5W O13 H6W 98.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 O5 2.079(2) y
Mn1 O2 2.102(2) y
Mn1 O3 2.171(2) y
Mn1 O6 2.188(2) y
Mn1 O7 2.282(2) y
Mn1 O8 2.306(2) y
Mn1 O13 2.580(12) y
C1 O1 1.251(4) y
C1 O2 1.256(4) y
C1 C2 1.491(4) ?
C2 C10 1.362(4) ?
C2 C3 1.439(4) ?
C3 O3 1.267(3) ?
C3 C4 1.452(4) ?
C4 C9 1.428(4) ?
C4 C5 1.429(4) ?
C5 N1 1.359(4) ?
C5 C6 1.377(4) ?
C6 F1 1.367(4) ?
C6 C7 1.387(5) ?
C7 C8 1.377(5) ?
C7 N3 1.381(4) ?
C8 F2 1.364(4) ?
C8 C9 1.380(4) ?
C9 N2 1.398(4) ?
C10 N2 1.336(4) ?
C10 H10 0.9300 ?
C11 N2 1.471(4) ?
C11 C12 1.478(5) ?
C11 C13 1.491(5) ?
C11 H11 0.9800 ?
C12 C13 1.491(5) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 N3 1.450(4) ?
C14 C15 1.457(5) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 N4 1.511(4) ?
C15 C18 1.530(5) ?
C15 H15 0.9800 ?
C16 C17 1.450(5) ?
C16 N4 1.493(4) ?
C16 C19 1.516(5) ?
C16 H16 0.9800 ?
C17 N3 1.470(4) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
N1 H1A 0.8600 ?
N1 H1B 0.8600 ?
N4 H4A 0.9000 ?
N4 H4B 0.9000 ?
C20 O4 1.254(4) y
C20 O5 1.257(4) y
C20 C21 1.492(4) ?
C21 C29 1.359(4) ?
C21 C22 1.436(4) ?
C22 O6 1.267(3) ?
C22 C23 1.457(4) ?
C23 C28 1.429(4) ?
C23 C24 1.434(4) ?
C24 N5 1.354(4) ?
C24 C25 1.380(4) ?
C25 F3 1.365(3) ?
C25 C26 1.375(4) ?
C26 C27 1.386(4) ?
C26 N7 1.398(4) ?
C27 F4 1.362(3) ?
C27 C28 1.378(4) ?
C28 N6 1.397(4) ?
C29 N6 1.343(4) ?
C29 H29 0.9300 ?
C30 N6 1.463(4) ?
C30 C31 1.482(5) ?
C30 C32 1.493(5) ?
C30 H30 0.9800 ?
C31 C32 1.498(5) ?
C31 H31A 0.9700 ?
C31 H31B 0.9700 ?
C32 H32A 0.9700 ?
C32 H32B 0.9700 ?
C33 N7 1.450(4) ?
C33 C34 1.519(5) ?
C33 H33A 0.9700 ?
C33 H33B 0.9700 ?
C34 N8 1.484(4) ?
C34 C37 1.524(4) ?
C34 H34 0.9800 ?
C35 N8 1.499(4) ?
C35 C36 1.499(4) ?
C35 C38 1.509(4) ?
C35 H35 0.9800 ?
C36 N7 1.453(4) ?
C36 H36A 0.9700 ?
C36 H36B 0.9700 ?
C37 H37A 0.9600 ?
C37 H37B 0.9600 ?
C37 H37C 0.9600 ?
C38 H38A 0.9600 ?
C38 H38B 0.9600 ?
C38 H38C 0.9600 ?
N5 H5A 0.8600 ?
N5 H5B 0.8600 ?
N8 H8A 0.9000 ?
N8 H8B 0.9000 ?
C39 C44 1.382(4) ?
C39 C40 1.385(4) ?
C39 C45 1.505(4) ?
C40 C41 1.397(4) ?
C40 H40 0.9300 ?
C41 C42 1.377(4) ?
C41 H41 0.9300 ?
C42 C43 1.376(5) ?
C42 C46 1.510(4) ?
C43 C44 1.380(5) ?
C43 H43 0.9300 ?
C44 H44 0.9300 ?
C45 O8 1.251(4) y
C45 O7 1.253(4) y
C46 O10 1.241(4) y
C46 O9 1.256(4) y
O11 H1W 0.8467 ?
O11 H2W 0.8454 ?
O12 H3W 0.8505 ?
O12 H4W 0.8491 ?
O13 H5W 0.9503 ?
O13 H6W 1.1238 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O8 3_565 0.86 2.24 3.041(3) 156
N1 H1B O3 . 0.86 2.02 2.651(3) 129
N4 H4A O1 4_566 0.90 1.80 2.647(4) 156
N4 H4B O11 2_545 0.90 2.01 2.845(3) 153
N5 H5A O8 3_565 0.86 2.13 2.954(3) 160
N5 H5B O6 . 0.86 2.01 2.651(3) 131
N8 H8A O4 4_576 0.90 1.85 2.750(3) 175
N8 H8B O11 2 0.90 1.94 2.821(3) 166
O11 H1W O9 1_656 0.85 1.76 2.606(3) 174
O11 H2W O7 3_665 0.85 1.97 2.804(3) 171
O12 H3W O10 3_565 0.85 2.11 2.924(4) 159
O12 H4W O10 1_656 0.85 2.00 2.844(4) 174
O13 H5W O2 3_665 0.95 2.41 3.000(12) 120
C13 H13B O4 3_665 0.97 2.56 3.526(5) 178
C35 H35 O12 2 0.98 2.38 3.321(4) 161
C38 H38A O13 2 0.96 2.51 3.097(12) 120
C12 H12A Cg9 4_666 0.97 2.59 3.529(4) 162
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
O1 C1 C2 C10 10.0(5)
O2 C1 C2 C10 -170.0(3)
O1 C1 C2 C3 -173.4(3)
O2 C1 C2 C3 6.6(5)
C10 C2 C3 O3 174.0(3)
C1 C2 C3 O3 -2.6(5)
C10 C2 C3 C4 -6.4(4)
C1 C2 C3 C4 177.0(3)
O3 C3 C4 C9 177.9(3)
C2 C3 C4 C9 -1.7(4)
O3 C3 C4 C5 -0.5(4)
C2 C3 C4 C5 179.9(3)
C9 C4 C5 N1 171.4(3)
C3 C4 C5 N1 -10.2(5)
C9 C4 C5 C6 -5.5(4)
C3 C4 C5 C6 172.9(3)
N1 C5 C6 F1 0.7(5)
C4 C5 C6 F1 177.7(3)
N1 C5 C6 C7 -175.4(3)
C4 C5 C6 C7 1.6(5)
F1 C6 C7 C8 -177.3(3)
C5 C6 C7 C8 -1.3(6)
F1 C6 C7 N3 -1.5(5)
C5 C6 C7 N3 174.6(4)
N3 C7 C8 F2 13.7(6)
C6 C7 C8 F2 -170.5(3)
N3 C7 C8 C9 -170.5(4)
C6 C7 C8 C9 5.3(5)
F2 C8 C9 N2 -13.1(5)
C7 C8 C9 N2 171.2(3)
F2 C8 C9 C4 166.2(3)
C7 C8 C9 C4 -9.6(5)
C5 C4 C9 C8 9.4(5)
C3 C4 C9 C8 -169.0(3)
C5 C4 C9 N2 -171.3(3)
C3 C4 C9 N2 10.2(4)
C3 C2 C10 N2 6.6(5)
C1 C2 C10 N2 -176.6(3)
N2 C11 C12 C13 -106.1(3)
N2 C11 C13 C12 109.6(3)
N3 C14 C15 N4 -51.3(4)
N3 C14 C15 C18 -174.7(3)
N4 C16 C17 N3 56.3(5)
C19 C16 C17 N3 179.7(3)
C2 C10 N2 C9 2.2(5)
C2 C10 N2 C11 -171.9(3)
C8 C9 N2 C10 168.7(3)
C4 C9 N2 C10 -10.6(4)
C8 C9 N2 C11 -17.4(5)
C4 C9 N2 C11 163.4(3)
C12 C11 N2 C10 114.2(3)
C13 C11 N2 C10 45.1(4)
C12 C11 N2 C9 -59.7(4)
C13 C11 N2 C9 -128.8(3)
C8 C7 N3 C14 -129.4(4)
C6 C7 N3 C14 55.0(6)
C8 C7 N3 C17 30.0(6)
C6 C7 N3 C17 -145.7(4)
C15 C14 N3 C7 -138.7(4)
C15 C14 N3 C17 60.5(5)
C16 C17 N3 C7 135.3(4)
C16 C17 N3 C14 -63.0(5)
C17 C16 N4 C15 -50.3(4)
C19 C16 N4 C15 -175.9(3)
C14 C15 N4 C16 47.4(4)
C18 C15 N4 C16 174.3(3)
O1 C1 O2 Mn1 163.6(3)
C2 C1 O2 Mn1 -16.4(5)
O5 Mn1 O2 C1 171.9(4)
O3 Mn1 O2 C1 15.5(4)
O6 Mn1 O2 C1 88.8(4)
O7 Mn1 O2 C1 -100.8(4)
O8 Mn1 O2 C1 -62.8(4)
C2 C3 O3 Mn1 7.0(4)
C4 C3 O3 Mn1 -172.56(19)
O5 Mn1 O3 C3 -93.1(3)
O2 Mn1 O3 C3 -10.0(3)
O6 Mn1 O3 C3 -153.5(3)
O7 Mn1 O3 C3 70.5(3)
O8 Mn1 O3 C3 120.7(3)
O4 C20 C21 C29 -7.0(4)
O5 C20 C21 C29 174.4(3)
O4 C20 C21 C22 175.4(3)
O5 C20 C21 C22 -3.1(5)
C29 C21 C22 O6 -171.0(3)
C20 C21 C22 O6 6.6(5)
C29 C21 C22 C23 9.9(4)
C20 C21 C22 C23 -172.6(3)
O6 C22 C23 C28 178.0(3)
C21 C22 C23 C28 -2.8(4)
O6 C22 C23 C24 -5.5(4)
C21 C22 C23 C24 173.7(3)
C28 C23 C24 N5 -172.9(3)
C22 C23 C24 N5 10.5(4)
C28 C23 C24 C25 3.5(4)
C22 C23 C24 C25 -173.1(3)
N5 C24 C25 F3 -1.4(4)
C23 C24 C25 F3 -178.0(3)
N5 C24 C25 C26 176.8(3)
C23 C24 C25 C26 0.3(5)
F3 C25 C26 C27 176.9(3)
C24 C25 C26 C27 -1.3(5)
F3 C25 C26 N7 -3.9(5)
C24 C25 C26 N7 177.9(3)
C25 C26 C27 F4 173.4(3)
N7 C26 C27 F4 -5.9(5)
C25 C26 C27 C28 -1.7(5)
N7 C26 C27 C28 179.1(3)
F4 C27 C28 N6 9.1(5)
C26 C27 C28 N6 -176.0(3)
F4 C27 C28 C23 -169.3(3)
C26 C27 C28 C23 5.6(5)
C24 C23 C28 C27 -6.3(4)
C22 C23 C28 C27 170.3(3)
C24 C23 C28 N6 175.2(3)
C22 C23 C28 N6 -8.1(4)
C22 C21 C29 N6 -6.4(5)
C20 C21 C29 N6 175.8(3)
N6 C30 C31 C32 106.8(3)
N6 C30 C32 C31 -108.5(3)
N7 C33 C34 N8 -54.7(4)
N7 C33 C34 C37 -174.6(3)
N8 C35 C36 N7 51.8(3)
C38 C35 C36 N7 170.3(3)
C21 C29 N6 C28 -5.1(5)
C21 C29 N6 C30 169.6(3)
C27 C28 N6 C29 -166.3(3)
C23 C28 N6 C29 12.2(4)
C27 C28 N6 C30 19.2(5)
C23 C28 N6 C30 -162.3(3)
C31 C30 N6 C29 -116.4(3)
C32 C30 N6 C29 -47.3(4)
C31 C30 N6 C28 58.1(4)
C32 C30 N6 C28 127.3(3)
C25 C26 N7 C33 -37.3(5)
C27 C26 N7 C33 141.8(4)
C25 C26 N7 C36 127.9(4)
C27 C26 N7 C36 -52.9(5)
C34 C33 N7 C26 -135.1(3)
C34 C33 N7 C36 58.6(4)
C35 C36 N7 C26 134.6(3)
C35 C36 N7 C33 -58.8(4)
C33 C34 N8 C35 54.3(3)
C37 C34 N8 C35 176.9(3)
C36 C35 N8 C34 -51.8(3)
C38 C35 N8 C34 -172.3(3)
O4 C20 O5 Mn1 -173.4(3)
C21 C20 O5 Mn1 5.1(6)
O2 Mn1 O5 C20 -148.0(4)
O3 Mn1 O5 C20 -67.6(5)
O6 Mn1 O5 C20 -6.4(4)
O7 Mn1 O5 C20 127.3(4)
O8 Mn1 O5 C20 75.3(4)
C21 C22 O6 Mn1 -11.2(4)
C23 C22 O6 Mn1 167.89(19)
O5 Mn1 O6 C22 9.3(3)
O2 Mn1 O6 C22 96.8(3)
O3 Mn1 O6 C22 168.7(3)
O7 Mn1 O6 C22 -70.2(3)
O8 Mn1 O6 C22 -104.8(3)
C44 C39 C40 C41 0.4(5)
C45 C39 C40 C41 179.8(3)
C39 C40 C41 C42 0.5(5)
C40 C41 C42 C43 -0.2(5)
C40 C41 C42 C46 178.7(3)
C41 C42 C43 C44 -0.9(5)
C46 C42 C43 C44 -179.8(3)
C42 C43 C44 C39 1.7(6)
C40 C39 C44 C43 -1.4(5)
C45 C39 C44 C43 179.1(3)
C44 C39 C45 O8 176.4(3)
C40 C39 C45 O8 -3.1(5)
C44 C39 C45 O7 -4.8(5)
C40 C39 C45 O7 175.7(3)
C43 C42 C46 O10 -156.2(4)
C41 C42 C46 O10 24.9(5)
C43 C42 C46 O9 25.0(5)
C41 C42 C46 O9 -153.9(4)
O8 C45 O7 Mn1 -0.2(3)
C39 C45 O7 Mn1 -179.0(2)
O5 Mn1 O7 C45 -119.6(2)
O2 Mn1 O7 C45 145.4(2)
O3 Mn1 O7 C45 66.9(2)
O6 Mn1 O7 C45 -42.6(2)
O8 Mn1 O7 C45 0.11(18)
O7 C45 O8 Mn1 0.2(3)
C39 C45 O8 Mn1 179.0(3)
O5 Mn1 O8 C45 70.51(19)
O2 Mn1 O8 C45 -47.3(2)
O3 Mn1 O8 C45 -123.57(18)
O6 Mn1 O8 C45 149.90(18)
O7 Mn1 O8 C45 -0.11(18)
