# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_b-zs14-67
_database_code_depnum_ccdc_archive 'CCDC 1586700'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H5 Mn N O4'
_chemical_formula_sum            'C13 H5 Mn N O4'
_chemical_formula_weight         294.12

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           67
_space_group_name_H-M_alt        'C m m a'
_space_group_name_Hall           '-C 2b 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z'
'x, -y, -z'
'-x, y+1/2, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1, -z'
'-x, -y, -z'
'x, y-1/2, -z'
'-x, y, z'
'x, -y-1/2, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z'
'-x+1/2, y+1/2, z'
'x+1/2, -y, z'

_cell_length_a                   12.783(3)
_cell_length_b                   41.280(8)
_cell_length_c                   8.1610(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4306.4(16)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7692
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.5

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_F_000             2352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.234
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7086
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         2.496
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2118
_reflns_number_gt                1388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1659P)²+4.7300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2015)'
_refine_ls_extinction_coef       0.0107(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2118
_refine_ls_number_parameters     230
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.2418
_refine_ls_wR_factor_gt          0.2047
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.000000 0.09979(2) 1.00069(5) 0.0140(4) Uani 1 2 d S T P . .
Mn2 Mn -0.250000 0.15022(2) 1.000000 0.0140(4) Uani 1 2 d S T P . .
N1 N 0.000000 0.06223(7) 1.1975(3) 0.0144(7) Uani 1 2 d S T P . .
C1 C 0.000000 0.06941(9) 1.3582(4) 0.0162(9) Uani 1 2 d S T P . .
H1 H 0.000000 0.091058 1.389763 0.019 Uiso 1 2 calc R U P . .
C2 C 0.000000 0.04558(12) 1.4790(5) 0.0156(10) Uani 1 2 d S T P . .
H2 H 0.000000 0.051490 1.588954 0.019 Uiso 1 2 calc R U P . .
C3 C 0.000000 0.01318(8) 1.4362(4) 0.0131(8) Uani 1 2 d S T P . .
C4 C 0.000000 0.00585(11) 1.2711(5) 0.0204(10) Uani 1 2 d S T P . .
H4 H 0.000000 -0.015660 1.237279 0.025 Uiso 1 2 calc R U P . .
C5 C 0.000000 0.03061(9) 1.1552(4) 0.0227(10) Uani 1 2 d S T P . .
H5 H 0.000000 0.025159 1.044594 0.027 Uiso 1 2 calc R U P . .
O1 O 0.12698(16) 0.07571(4) 0.8861(2) 0.0184(6) Uani 1 1 d . . . . .
O2 O 0.23984(15) 0.11498(6) 0.8145(3) 0.0177(6) Uani 1 1 d . . . . .
O3 O 0.000000 0.13509(7) 0.8144(4) 0.0228(8) Uani 1 2 d S T P . .
O4 O -0.1205(3) 0.17482(9) 0.8888(4) 0.0199(9) Uani 0.5 1 d . . P . .
O5 O 0.000000 0.13484(8) 0.1850(4) 0.0240(8) Uani 1 2 d S T P . .
O6 O 0.1244(3) 0.17375(9) 0.1172(4) 0.0200(9) Uani 0.5 1 d . . P . .
N2 N -0.2527(2) 0.18804(9) 0.8026(4) 0.0133(12) Uani 0.5 1 d G . P . .
C6 C -0.2512(3) 0.17991(7) 0.6373(5) 0.0153(13) Uani 0.5 1 d G U P . .
C7 C -0.2501(3) 0.20415(9) 0.5191(4) 0.0175(14) Uani 0.5 1 d G . P . .
C8 C -0.2505(3) 0.23651(8) 0.5661(4) 0.0132(12) Uani 0.5 1 d G . P . .
C9 C -0.2520(3) 0.24464(8) 0.7314(4) 0.026(2) Uani 0.5 1 d G . P . .
C10 C -0.2531(3) 0.22040(9) 0.8496(3) 0.0253(17) Uani 0.5 1 d G . P . .
C11 C 0.1962(2) 0.08812(6) 0.7942(3) 0.0149(7) Uani 1 1 d . . . . .
C12 C 0.2277(2) 0.06902(8) 0.6436(3) 0.0151(7) Uani 1 1 d . . . . .
C13 C 0.250000 0.08604(13) 0.500000 0.0186(12) Uani 1 2 d S T P . .
H13 H 0.249999 0.108564 0.499999 0.022 Uiso 1 2 calc R U P . .
C14 C 0.2277(2) 0.03532(8) 0.6429(3) 0.0146(7) Uani 1 1 d . . . . .
H14 H 0.212579 0.024160 0.739061 0.018 Uiso 1 1 calc R U . . .
C15 C 0.250000 0.01793(12) 0.500000 0.0158(11) Uani 1 2 d S T P . .
C16 C -0.0534(4) 0.16203(12) 0.7954(6) 0.0139(11) Uani 0.5 1 d . . P . .
C17 C 0.000000 0.18124(14) 0.6448(6) 0.0446(14) Uani 1 2 d S TU P . .
C18 C 0.000000 0.16384(13) 0.5015(3) 0.0146(11) Uani 1 2 d S T P . .
H18 H 0.000000 0.141310 0.502283 0.017 Uiso 1 2 calc R U P . .
C19 C 0.000000 0.18087(14) 0.3568(6) 0.0475(15) Uani 1 2 d S TU P . .
C20 C 0.0550(4) 0.16151(12) 0.2065(6) 0.0136(11) Uani 0.5 1 d . . P . .
C21 C 0.000000 0.21446(14) 0.3572(6) 0.0437(14) Uani 1 2 d S TU P . .
H21 H 0.000000 0.225369 0.257513 0.052 Uiso 1 2 calc R U P . .
C22 C 0.000000 0.23214(13) 0.4992(4) 0.0163(11) Uani 1 2 d S T P . .
C23 C 0.000000 0.21493(14) 0.6424(6) 0.0435(14) Uani 1 2 d S TU P . .
H23 H 0.000000 0.226104 0.741369 0.052 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O5 2.087(3) 1_556 ?
Mn1 O3 2.106(3) . ?
Mn1 O1 2.1206(19) 11 ?
Mn1 O1 2.1206(19) . ?
Mn1 N1 2.232(3) . ?
Mn2 O2 2.104(3) 11 ?
Mn2 O2 2.104(3) 14_457 ?
Mn2 O6 2.106(4) 11_556 ?
Mn2 O6 2.106(4) 14_456 ?
Mn2 O4 2.144(4) 8_447 ?
Mn2 O4 2.144(4) . ?
Mn2 N2 2.244(3) . ?
Mn2 N2 2.244(3) 8_447 ?
N1 C1 1.344(4) . ?
N1 C5 1.350(5) . ?
C1 C2 1.393(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(5) . ?
C3 C3 1.506(6) 9_558 ?
C4 C5 1.393(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
O1 C11 1.269(3) . ?
O2 C11 1.252(4) . ?
O3 C16 1.314(6) 11 ?
O3 C16 1.314(6) . ?
O4 C16 1.263(6) . ?
O5 C20 1.318(6) . ?
O5 C20 1.318(6) 11 ?
O6 C20 1.254(6) . ?
O6 N2 1.802(5) 14_556 ?
N2 C6 1.3900 . ?
N2 C10 1.3900 . ?
C6 C7 1.3900 . ?
C6 C7 1.622(5) 8_446 ?
C7 C7 0.311(6) 8_446 ?
C7 C8 1.3900 . ?
C7 C8 1.506(3) 8_446 ?
C8 C8 1.079(7) 8_446 ?
C8 C8 1.114(7) 12_565 ?
C8 C9 1.3900 . ?
C8 C8 1.551(6) 13_456 ?
C8 C9 1.557(3) 12_565 ?
C9 C9 0.443(6) 12_565 ?
C9 C10 1.3900 . ?
C9 C10 1.736(7) 12_565 ?
C11 C12 1.514(4) . ?
C12 C14 1.391(4) . ?
C12 C13 1.396(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.399(4) . ?
C14 H14 0.9300 . ?
C15 C15 1.480(10) 6_545 ?
C16 C16 1.364(10) 11 ?
C16 C17 1.614(7) . ?
C17 C18 1.372(6) . ?
C17 C23 1.391(7) . ?
C18 C19 1.374(6) . ?
C18 H18 0.9300 . ?
C19 C21 1.386(7) . ?
C19 C20 1.625(7) 11 ?
C19 C20 1.625(7) . ?
C20 C20 1.407(10) 11 ?
C21 C22 1.370(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(6) . ?
C22 C22 1.475(10) 2 ?
C23 H23 0.9300 . ?

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
O5 Mn1 O3 92.34(15) 1_556 . ?
O5 Mn1 O1 129.99(5) 1_556 11 ?
O3 Mn1 O1 90.35(8) . 11 ?
O5 Mn1 O1 129.99(5) 1_556 . ?
O3 Mn1 O1 90.35(8) . . ?
O1 Mn1 O1 99.89(10) 11 . ?
O5 Mn1 N1 87.87(12) 1_556 . ?
O3 Mn1 N1 179.78(11) . . ?
O1 Mn1 N1 89.51(7) 11 . ?
O1 Mn1 N1 89.51(7) . . ?
O2 Mn2 O2 92.49(14) 11 14_457 ?
O2 Mn2 O6 126.77(12) 11 11_556 ?
O2 Mn2 O6 92.25(12) 14_457 11_556 ?
O2 Mn2 O6 92.25(12) 11 14_456 ?
O2 Mn2 O6 126.77(12) 14_457 14_456 ?
O6 Mn2 O6 125.1(2) 11_556 14_456 ?
O2 Mn2 O4 132.83(12) 11 8_447 ?
O2 Mn2 O4 88.58(12) 14_457 8_447 ?
O6 Mn2 O4 100.27(17) 11_556 8_447 ?
O6 Mn2 O4 52.05(16) 14_456 8_447 ?
O2 Mn2 O4 88.58(12) 11 . ?
O2 Mn2 O4 132.83(12) 14_457 . ?
O6 Mn2 O4 52.05(16) 11_556 . ?
O6 Mn2 O4 100.27(17) 14_456 . ?
O4 Mn2 O4 123.5(2) 8_447 . ?
O2 Mn2 N2 88.02(14) 11 . ?
O2 Mn2 N2 175.58(9) 14_457 . ?
O6 Mn2 N2 90.96(13) 11_556 . ?
O6 Mn2 N2 48.81(13) 14_456 . ?
O4 Mn2 N2 87.86(13) 8_447 . ?
O4 Mn2 N2 51.56(13) . . ?
O2 Mn2 N2 175.58(9) 11 8_447 ?
O2 Mn2 N2 88.02(14) 14_457 8_447 ?
O6 Mn2 N2 48.81(13) 11_556 8_447 ?
O6 Mn2 N2 90.96(13) 14_456 8_447 ?
O4 Mn2 N2 51.56(13) 8_447 8_447 ?
O4 Mn2 N2 87.86(13) . 8_447 ?
N2 Mn2 N2 91.8(2) . 8_447 ?
C1 N1 C5 117.6(3) . . ?
C1 N1 Mn1 123.3(2) . . ?
C5 N1 Mn1 119.2(2) . . ?
N1 C1 C2 122.3(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 C3 121.1(4) . 9_558 ?
C2 C3 C3 121.6(4) . 9_558 ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 122.4(3) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C11 O1 Mn1 127.27(16) . . ?
C11 O2 Mn2 137.3(2) . 14_557 ?
C16 O3 C16 62.5(5) 11 . ?
C16 O3 Mn1 132.1(3) 11 . ?
C16 O3 Mn1 132.1(3) . . ?
C16 O4 Mn2 125.6(3) . . ?
C20 O5 C20 64.5(5) . 11 ?
C20 O5 Mn1 132.4(3) . 1_554 ?
C20 O5 Mn1 132.4(3) 11 1_554 ?
C20 O6 N2 122.5(3) . 14_556 ?
C20 O6 Mn2 128.1(3) . 14_556 ?
N2 O6 Mn2 69.57(15) 14_556 14_556 ?
C6 N2 C10 120.0 . . ?
C6 N2 O6 106.6(2) . 14_456 ?
C10 N2 O6 102.2(2) . 14_456 ?
C6 N2 Mn2 121.91(19) . . ?
C10 N2 Mn2 118.07(19) . . ?
O6 N2 Mn2 61.61(14) 14_456 . ?
N2 C6 C7 120.0 . . ?
N2 C6 C7 127.95(13) . 8_446 ?
C7 C7 C8 106.0 8_446 . ?
C7 C7 C6 134.0 8_446 . ?
C8 C7 C6 120.0 . . ?
C7 C7 C8 62.5(2) 8_446 8_446 ?
C6 C7 C8 163.5(2) . 8_446 ?
C8 C7 C6 144.11(16) . 8_446 ?
C6 C7 C6 95.89(16) . 8_446 ?
C8 C7 C6 100.6(3) 8_446 8_446 ?
C8 C8 C8 90.0 8_446 12_565 ?
C8 C8 C7 74.0 8_446 . ?
C8 C8 C7 164.0 12_565 . ?
C8 C8 C9 166.0 8_446 . ?
C8 C8 C9 76.0 12_565 . ?
C7 C8 C9 120.0 . . ?
C8 C8 C7 62.51(19) 8_446 8_446 ?
C8 C8 C7 152.50(19) 12_565 8_446 ?
C9 C8 C7 131.46(19) . 8_446 ?
C8 C8 C8 45.9(4) 8_446 13_456 ?
C7 C8 C8 119.9(4) . 13_456 ?
C9 C8 C8 120.1(4) . 13_456 ?
C7 C8 C8 108.4(5) 8_446 13_456 ?
C8 C8 C9 150.0(2) 8_446 12_565 ?
C8 C8 C9 60.0(2) 12_565 12_565 ?
C7 C8 C9 136.0(2) . 12_565 ?
C7 C8 C9 147.5(3) 8_446 12_565 ?
C8 C8 C9 104.1(5) 13_456 12_565 ?
C9 C9 C8 104.0 12_565 . ?
C9 C9 C10 136.0 12_565 . ?
C8 C9 C10 120.0 . . ?
C9 C9 C8 60.0(2) 12_565 12_565 ?
C10 C9 C8 163.9(2) . 12_565 ?
C8 C9 C10 137.74(14) . 12_565 ?
C10 C9 C10 102.26(14) . 12_565 ?
C8 C9 C10 93.8(3) 12_565 12_565 ?
C9 C10 N2 120.0 . . ?
N2 C10 C9 130.20(12) . 12_565 ?
O2 C11 O1 126.2(2) . . ?
O2 C11 C12 116.8(2) . . ?
O1 C11 C12 117.1(2) . . ?
C14 C12 C13 120.0(3) . . ?
C14 C12 C11 121.6(3) . . ?
C13 C12 C11 118.3(3) . . ?
C12 C13 C12 119.6(5) . 8_546 ?
C12 C13 H13 120.2 . . ?
C12 C13 H13 120.2 8_546 . ?
C12 C14 C15 121.1(3) . . ?
C12 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C14 118.3(4) 8_546 . ?
C14 C15 C15 120.9(2) 8_546 6_545 ?
C14 C15 C15 120.9(2) . 6_545 ?
O4 C16 O3 129.4(4) . . ?
O4 C16 C16 132.8(3) . 11 ?
O3 C16 C16 58.7(2) . 11 ?
O4 C16 C17 122.8(4) . . ?
O3 C16 C17 106.6(4) . . ?
C16 C16 C17 65.0(2) 11 . ?
C18 C17 C23 120.8(5) . . ?
C18 C17 C16 113.1(4) . . ?
C23 C17 C16 120.1(4) . . ?
C18 C17 C16 113.1(4) . 11 ?
C23 C17 C16 120.1(4) . 11 ?
C16 C17 C16 50.0(4) . 11 ?
C17 C18 C19 117.7(5) . . ?
C17 C18 H18 121.2 . . ?
C19 C18 H18 121.2 . . ?
C18 C19 C21 120.6(5) . . ?
C18 C19 C20 113.4(4) . 11 ?
C21 C19 C20 119.6(4) . 11 ?
C18 C19 C20 113.4(4) . . ?
C21 C19 C20 119.6(4) . . ?
C20 C19 C20 51.3(4) 11 . ?
O6 C20 O5 129.5(5) . . ?
O6 C20 C20 135.0(3) . 11 ?
O5 C20 C20 57.8(2) . 11 ?
O6 C20 C19 123.1(4) . . ?
O5 C20 C19 106.3(4) . . ?
C20 C20 C19 64.3(2) 11 . ?
C22 C21 C19 122.3(5) . . ?
C22 C21 H21 118.8 . . ?
C19 C21 H21 118.8 . . ?
C23 C22 C21 116.5(5) . . ?
C23 C22 C22 121.3(3) . 2 ?
C21 C22 C22 122.2(3) . 2 ?
C22 C23 C17 122.1(4) . . ?
C22 C23 H23 119.0 . . ?
C17 C23 H23 119.0 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.000(2) . . . . ?
Mn1 N1 C1 C2 180.000(1) . . . . ?
N1 C1 C2 C3 0.000(2) . . . . ?
C1 C2 C3 C4 0.000(2) . . . . ?
C1 C2 C3 C3 180.000(1) . . . 9_558 ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C3 C4 C5 180.000(1) 9_558 . . . ?
C1 N1 C5 C4 0.000(1) . . . . ?
Mn1 N1 C5 C4 180.000(1) . . . . ?
C3 C4 C5 N1 0.000(1) . . . . ?
C10 N2 C6 C7 0.0 . . . . ?
O6 N2 C6 C7 115.2(2) 14_456 . . . ?
Mn2 N2 C6 C7 -178.3(2) . . . . ?
C10 N2 C6 C7 0.0(4) . . . 8_446 ?
O6 N2 C6 C7 115.2(5) 14_456 . . 8_446 ?
Mn2 N2 C6 C7 -178.3(4) . . . 8_446 ?
N2 C6 C7 C7 -180(2) . . . 8_446 ?
N2 C6 C7 C8 0.0 . . . . ?
C7 C6 C7 C8 180(100) 8_446 . . . ?
N2 C6 C7 C8 -0.3(15) . . . 8_446 ?
C7 C6 C7 C8 179(100) 8_446 . . 8_446 ?
N2 C6 C7 C6 -180.0(5) . . . 8_446 ?
C7 C6 C7 C6 0(2) 8_446 . . 8_446 ?
C7 C7 C8 C8 -0.1(13) 8_446 . . 8_446 ?
C6 C7 C8 C8 -179.9(6) . . . 8_446 ?
C6 C7 C8 C8 0.1(6) 8_446 . . 8_446 ?
C7 C7 C8 C8 -0.1(19) 8_446 . . 12_565 ?
C6 C7 C8 C8 -179.9 . . . 12_565 ?
C8 C7 C8 C8 0.0(6) 8_446 . . 12_565 ?
C6 C7 C8 C8 0.1(9) 8_446 . . 12_565 ?
C7 C7 C8 C9 179.8(19) 8_446 . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C8 C7 C8 C9 179.9(6) 8_446 . . . ?
C6 C7 C8 C9 180.0(9) 8_446 . . . ?
C6 C7 C8 C7 -179.8(19) . . . 8_446 ?
C8 C7 C8 C7 0.1(13) 8_446 . . 8_446 ?
C6 C7 C8 C7 0.2(10) 8_446 . . 8_446 ?
C7 C7 C8 C8 -0.1(15) 8_446 . . 13_456 ?
C6 C7 C8 C8 -179.9(5) . . . 13_456 ?
C8 C7 C8 C8 0.0(2) 8_446 . . 13_456 ?
C6 C7 C8 C8 0.1(8) 8_446 . . 13_456 ?
C7 C7 C8 C9 179.8(19) 8_446 . . 12_565 ?
C6 C7 C8 C9 0.0 . . . 12_565 ?
C8 C7 C8 C9 179.9(6) 8_446 . . 12_565 ?
C6 C7 C8 C9 180.0(9) 8_446 . . 12_565 ?
C8 C8 C9 C9 0(2) 8_446 . . 12_565 ?
C8 C8 C9 C9 0.0 12_565 . . 12_565 ?
C7 C8 C9 C9 -180.0 . . . 12_565 ?
C7 C8 C9 C9 -179.9(5) 8_446 . . 12_565 ?
C8 C8 C9 C9 -0.1(5) 13_456 . . 12_565 ?
C8 C8 C9 C10 180(100) 8_446 . . . ?
C8 C8 C9 C10 180.0 12_565 . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C7 C8 C9 C10 0.1(5) 8_446 . . . ?
C8 C8 C9 C10 179.9(5) 13_456 . . . ?
C9 C8 C9 C10 180.0 12_565 . . . ?
C8 C8 C9 C8 0(2) 8_446 . . 12_565 ?
C7 C8 C9 C8 -180.0 . . . 12_565 ?
C7 C8 C9 C8 -179.9(5) 8_446 . . 12_565 ?
C8 C8 C9 C8 -0.1(5) 13_456 . . 12_565 ?
C9 C8 C9 C8 0.0 12_565 . . 12_565 ?
C8 C8 C9 C10 0(2) 8_446 . . 12_565 ?
C8 C8 C9 C10 0.0 12_565 . . 12_565 ?
C7 C8 C9 C10 -179.9 . . . 12_565 ?
C7 C8 C9 C10 -179.9(5) 8_446 . . 12_565 ?
C8 C8 C9 C10 -0.1(5) 13_456 . . 12_565 ?
C9 C8 C9 C10 0.0 12_565 . . 12_565 ?
C9 C9 C10 N2 180.0 12_565 . . . ?
C8 C9 C10 N2 0.0 . . . . ?
C8 C9 C10 N2 0.1 12_565 . . . ?
C10 C9 C10 N2 180.0 12_565 . . . ?
C8 C9 C10 C9 -180.0 . . . 12_565 ?
C8 C9 C10 C9 -180(100) 12_565 . . 12_565 ?
C10 C9 C10 C9 0.0 12_565 . . 12_565 ?
C6 N2 C10 C9 0.0 . . . . ?
O6 N2 C10 C9 -117.5(2) 14_456 . . . ?
Mn2 N2 C10 C9 178.33(19) . . . . ?
C6 N2 C10 C9 0.0 . . . 12_565 ?
O6 N2 C10 C9 -117.5(2) 14_456 . . 12_565 ?
Mn2 N2 C10 C9 178.34(19) . . . 12_565 ?
Mn2 O2 C11 O1 11.1(5) 14_557 . . . ?
Mn2 O2 C11 C12 -170.30(19) 14_557 . . . ?
Mn1 O1 C11 O2 40.3(4) . . . . ?
Mn1 O1 C11 C12 -138.34(19) . . . . ?
O2 C11 C12 C14 148.8(3) . . . . ?
O1 C11 C12 C14 -32.5(4) . . . . ?
O2 C11 C12 C13 -35.7(3) . . . . ?
O1 C11 C12 C13 143.1(2) . . . . ?
C14 C12 C13 C12 -0.07(19) . . . 8_546 ?
C11 C12 C13 C12 -175.7(3) . . . 8_546 ?
C13 C12 C14 C15 0.1(4) . . . . ?
C11 C12 C14 C15 175.6(2) . . . . ?
C12 C14 C15 C14 -0.07(19) . . . 8_546 ?
C12 C14 C15 C15 179.93(19) . . . 6_545 ?
Mn2 O4 C16 O3 -48.1(7) . . . . ?
Mn2 O4 C16 C16 -129.2(3) . . . 11 ?
Mn2 O4 C16 C17 145.9(3) . . . . ?
C16 O3 C16 O4 -121.9(5) 11 . . . ?
Mn1 O3 C16 O4 1.4(7) . . . . ?
Mn1 O3 C16 C16 123.3(4) . . . 11 ?
C16 O3 C16 C17 45.8(4) 11 . . . ?
Mn1 O3 C16 C17 169.1(2) . . . . ?
O4 C16 C17 C18 -132.3(4) . . . . ?
O3 C16 C17 C18 58.9(4) . . . . ?
C16 C16 C17 C18 101.5(3) 11 . . . ?
O4 C16 C17 C23 20.5(6) . . . . ?
O3 C16 C17 C23 -148.2(3) . . . . ?
C16 C16 C17 C23 -105.7(3) 11 . . . ?
O4 C16 C17 C16 126.2(4) . . . 11 ?
O3 C16 C17 C16 -42.5(4) . . . 11 ?
C23 C17 C18 C19 0.000(2) . . . . ?
C16 C17 C18 C19 152.6(3) . . . . ?
C16 C17 C18 C19 -152.6(3) 11 . . . ?
C17 C18 C19 C21 0.000(2) . . . . ?
C17 C18 C19 C20 -151.8(3) . . . 11 ?
C17 C18 C19 C20 151.8(3) . . . . ?
N2 O6 C20 O5 -133.2(5) 14_556 . . . ?
Mn2 O6 C20 O5 -44.7(7) 14_556 . . . ?
N2 O6 C20 C20 145.6(2) 14_556 . . 11 ?
Mn2 O6 C20 C20 -125.9(3) 14_556 . . 11 ?
N2 O6 C20 C19 60.1(6) 14_556 . . . ?
Mn2 O6 C20 C19 148.6(3) 14_556 . . . ?
C20 O5 C20 O6 -124.3(5) 11 . . . ?
Mn1 O5 C20 O6 0.9(7) 1_554 . . . ?
Mn1 O5 C20 C20 125.2(4) 1_554 . . 11 ?
C20 O5 C20 C19 44.2(4) 11 . . . ?
Mn1 O5 C20 C19 169.4(2) 1_554 . . . ?
C18 C19 C20 O6 -129.5(4) . . . . ?
C21 C19 C20 O6 22.7(6) . . . . ?
C20 C19 C20 O6 128.5(4) 11 . . . ?
C18 C19 C20 O5 61.2(4) . . . . ?
C21 C19 C20 O5 -146.6(3) . . . . ?
C20 C19 C20 O5 -40.8(4) 11 . . . ?
C18 C19 C20 C20 102.0(3) . . . 11 ?
C21 C19 C20 C20 -105.8(3) . . . 11 ?
C18 C19 C21 C22 0.000(2) . . . . ?
C20 C19 C21 C22 150.1(3) 11 . . . ?
C20 C19 C21 C22 -150.1(3) . . . . ?
C19 C21 C22 C23 0.000(2) . . . . ?
C19 C21 C22 C22 180.000(1) . . . 2 ?
C21 C22 C23 C17 0.000(2) . . . . ?
C22 C22 C23 C17 180.000(2) 2 . . . ?
C18 C17 C23 C22 0.000(2) . . . . ?
C16 C17 C23 C22 -150.8(3) . . . . ?
C16 C17 C23 C22 150.7(3) 11 . . . ?

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
C1 H1 O5 0.93 2.46 3.048(5) 121.2 1_556

_refine_diff_density_max         1.039
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.155

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sf171102a-2
_database_code_depnum_ccdc_archive 'CCDC 1586703'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H17 Mn N4 O4), H4 O'
_chemical_formula_sum            'C44 H38 Mn2 N8 O9'
_chemical_formula_weight         932.70

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6821(6)
_cell_length_b                   10.2379(7)
_cell_length_c                   12.0940(9)
_cell_angle_alpha                68.497(2)
_cell_angle_beta                 84.952(2)
_cell_angle_gamma                89.683(2)
_cell_volume                     995.88(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9139
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.705
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9096
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.840
_diffrn_reflns_theta_max         26.880
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4235
_reflns_number_gt                3048
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+0.9571P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4235
_refine_ls_number_parameters     289
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.00266(6) 0.36748(5) 0.38002(4) 0.02207(16) Uani 1 1 d . . . . .
O1 O 0.0478(3) 0.1502(2) 0.37927(18) 0.0274(5) Uani 1 1 d . . . . .
O2 O -0.0486(3) 0.3001(2) 0.2204(2) 0.0330(6) Uani 1 1 d . . . . .
O3 O -0.1065(3) -0.3563(2) 0.46441(18) 0.0316(6) Uani 1 1 d . . . . .
O4 O -0.0811(3) -0.4260(2) 0.31029(19) 0.0317(6) Uani 1 1 d . . . . .
O5 O 0.8434(6) 0.5606(5) 0.0450(4) 0.0433(13) Uani 0.5 1 d . U P . .
H5A H 0.857702 0.481779 0.093178 0.065 Uiso 1 1 d R U . . .
H5B H 0.768292 0.555120 0.010098 0.065 Uiso 1 1 d R U . . .
N1 N 0.2320(3) 0.4478(3) 0.2810(2) 0.0319(7) Uani 1 1 d . . . . .
N2 N 0.4377(3) 0.5866(3) 0.2028(2) 0.0316(7) Uani 1 1 d . . . . .
N3 N 0.5798(3) 1.1283(3) -0.4227(2) 0.0302(6) Uani 1 1 d . . . . .
N4 N 0.7708(3) 1.2778(3) -0.5224(2) 0.0296(6) Uani 1 1 d . . . . .
C1 C -0.0068(4) 0.1787(3) 0.2804(3) 0.0209(7) Uani 1 1 d . . . . .
C2 C -0.0221(3) 0.0622(3) 0.2333(2) 0.0174(6) Uani 1 1 d . . . . .
C3 C -0.0474(3) -0.0748(3) 0.3131(3) 0.0189(6) Uani 1 1 d . . . . .
H3 H -0.058064 -0.094165 0.394768 0.023 Uiso 1 1 calc R U . . .
C4 C -0.0568(3) -0.1830(3) 0.2703(2) 0.0185(6) Uani 1 1 d . . . . .
C5 C -0.0359(3) -0.1525(3) 0.1475(3) 0.0203(6) Uani 1 1 d . . . . .
H5 H -0.038171 -0.225862 0.119613 0.024 Uiso 1 1 calc R U . . .
C6 C -0.0118(3) -0.0158(3) 0.0657(2) 0.0172(6) Uani 1 1 d . . . . .
C7 C -0.0069(3) 0.0914(3) 0.1118(2) 0.0183(6) Uani 1 1 d . . . . .
H7 H 0.006796 0.184234 0.059432 0.022 Uiso 1 1 calc R U . . .
C8 C -0.0830(3) -0.3327(3) 0.3551(3) 0.0202(6) Uani 1 1 d . . . . .
C9 C 0.3372(5) 0.3825(4) 0.2298(3) 0.0419(10) Uani 1 1 d . . . . .
H9 H 0.323484 0.293007 0.228717 0.050 Uiso 1 1 calc R U . . .
C10 C 0.4642(5) 0.4663(4) 0.1811(4) 0.0451(10) Uani 1 1 d . . . . .
H10 H 0.551888 0.446147 0.140862 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2971(4) 0.5712(4) 0.2616(3) 0.0336(8) Uani 1 1 d . . . . .
H11 H 0.250705 0.639441 0.285954 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5339(4) 0.7145(4) 0.1532(3) 0.0361(9) Uani 1 1 d . . . . .
H12A H 0.641305 0.690692 0.164018 0.043 Uiso 1 1 calc R U . . .
H12B H 0.505362 0.775542 0.196505 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5176(4) 0.7927(3) 0.0216(3) 0.0287(8) Uani 1 1 d . . . . .
C14 C 0.6251(4) 0.8973(4) -0.0448(3) 0.0311(8) Uani 1 1 d . . . . .
H14 H 0.703650 0.920606 -0.007182 0.037 Uiso 1 1 calc R U . . .
C15 C 0.6183(4) 0.9681(4) -0.1664(3) 0.0310(8) Uani 1 1 d . . . . .
H15 H 0.692785 1.037138 -0.209316 0.037 Uiso 1 1 calc R U . . .
C16 C 0.5022(4) 0.9369(3) -0.2238(3) 0.0260(7) Uani 1 1 d . . . . .
C17 C 0.3914(4) 0.8353(4) -0.1569(3) 0.0329(8) Uani 1 1 d . . . . .
H17 H 0.311223 0.813930 -0.194267 0.040 Uiso 1 1 calc R U . . .
C18 C 0.3979(4) 0.7650(4) -0.0357(3) 0.0348(8) Uani 1 1 d . . . . .
H18 H 0.321093 0.698494 0.007762 0.042 Uiso 1 1 calc R U . . .
C19 C 0.4965(4) 0.9950(4) -0.3572(3) 0.0391(9) Uani 1 1 d . . . . .
H19A H 0.537867 0.925729 -0.388303 0.047 Uiso 1 1 calc R U . . .
H19B H 0.388963 1.006658 -0.373842 0.047 Uiso 1 1 calc R U . . .
C20 C 0.5194(4) 1.2602(4) -0.4586(3) 0.0410(9) Uani 1 1 d . . . . .
H20 H 0.417656 1.282844 -0.444088 0.049 Uiso 1 1 calc R U . . .
C21 C 0.6376(5) 1.3504(4) -0.5191(3) 0.0413(9) Uani 1 1 d . . . . .
H21 H 0.630124 1.447431 -0.553461 0.050 Uiso 1 1 calc R U . . .
C22 C 0.7303(4) 1.1451(3) -0.4637(3) 0.0275(7) Uani 1 1 d . . . . .
H22 H 0.797807 1.071371 -0.451938 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O4 2.120(2) 1_565 ?
Mn1 O3 2.122(2) 2_556 ?
Mn1 N1 2.225(3) . ?
Mn1 N4 2.258(3) 1_446 ?
Mn1 O1 2.260(2) . ?
Mn1 O2 2.351(2) . ?
Mn1 C1 2.631(3) . ?
O1 C1 1.258(4) . ?
O2 C1 1.258(4) . ?
O3 C8 1.252(3) . ?
O4 C8 1.258(3) . ?
O5 H5A 0.8200 . ?
O5 H5B 0.8201 . ?
N1 C11 1.318(4) . ?
N1 C9 1.364(4) . ?
N2 C11 1.337(4) . ?
N2 C10 1.365(4) . ?
N2 C12 1.456(4) . ?
N3 C22 1.344(4) . ?
N3 C20 1.375(4) . ?
N3 C19 1.460(4) . ?
N4 C22 1.315(4) . ?
N4 C21 1.376(4) . ?
C1 C2 1.510(4) . ?
C2 C7 1.382(4) . ?
C2 C3 1.385(4) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(4) . ?
C4 C8 1.505(4) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(4) . ?
C6 C6 1.496(5) 2 ?
C7 H7 0.9300 . ?
C9 C10 1.351(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.516(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.383(5) . ?
C13 C18 1.384(5) . ?
C14 C15 1.387(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(5) . ?
C16 C19 1.507(5) . ?
C17 C18 1.383(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.350(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
O4 Mn1 O3 105.03(8) 1_565 2_556 ?
O4 Mn1 N1 89.19(10) 1_565 . ?
O3 Mn1 N1 86.33(10) 2_556 . ?
O4 Mn1 N4 92.62(10) 1_565 1_446 ?
O3 Mn1 N4 94.97(9) 2_556 1_446 ?
N1 Mn1 N4 177.42(10) . 1_446 ?
O4 Mn1 O1 154.26(8) 1_565 . ?
O3 Mn1 O1 100.69(8) 2_556 . ?
N1 Mn1 O1 91.47(9) . . ?
N4 Mn1 O1 86.10(9) 1_446 . ?
O4 Mn1 O2 97.33(8) 1_565 . ?
O3 Mn1 O2 156.53(9) 2_556 . ?
N1 Mn1 O2 86.95(9) . . ?
N4 Mn1 O2 90.99(9) 1_446 . ?
O1 Mn1 O2 57.04(7) . . ?
O4 Mn1 C1 125.74(9) 1_565 . ?
O3 Mn1 C1 129.09(9) 2_556 . ?
N1 Mn1 C1 90.48(10) . . ?
N4 Mn1 C1 86.97(9) 1_446 . ?
O1 Mn1 C1 28.54(8) . . ?
O2 Mn1 C1 28.56(8) . . ?
C1 O1 Mn1 92.33(17) . . ?
C1 O2 Mn1 88.14(17) . . ?
C8 O3 Mn1 145.1(2) . 2_556 ?
C8 O4 Mn1 128.5(2) . 1_545 ?
H5A O5 H5B 107.7 . . ?
C11 N1 C9 104.7(3) . . ?
C11 N1 Mn1 126.3(2) . . ?
C9 N1 Mn1 129.0(2) . . ?
C11 N2 C10 106.8(3) . . ?
C11 N2 C12 126.9(3) . . ?
C10 N2 C12 125.5(3) . . ?
C22 N3 C20 106.6(3) . . ?
C22 N3 C19 126.3(3) . . ?
C20 N3 C19 127.1(3) . . ?
C22 N4 C21 105.0(3) . . ?
C22 N4 Mn1 127.8(2) . 1_664 ?
C21 N4 Mn1 127.0(2) . 1_664 ?
O1 C1 O2 122.2(3) . . ?
O1 C1 C2 118.3(3) . . ?
O2 C1 C2 119.5(3) . . ?
O1 C1 Mn1 59.13(14) . . ?
O2 C1 Mn1 63.30(15) . . ?
C2 C1 Mn1 174.6(2) . . ?
C7 C2 C3 120.4(3) . . ?
C7 C2 C1 120.3(3) . . ?
C3 C2 C1 119.3(3) . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 C8 120.6(3) . . ?
C5 C4 C8 119.9(2) . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 117.1(2) . . ?
C5 C6 C6 121.6(3) . 2 ?
C7 C6 C6 121.2(3) . 2 ?
C2 C7 C6 121.5(3) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
O3 C8 O4 124.5(3) . . ?
O3 C8 C4 118.4(3) . . ?
O4 C8 C4 117.1(3) . . ?
C10 C9 N1 110.4(3) . . ?
C10 C9 H9 124.8 . . ?
N1 C9 H9 124.8 . . ?
C9 C10 N2 106.0(3) . . ?
C9 C10 H10 127.0 . . ?
N2 C10 H10 127.0 . . ?
N1 C11 N2 112.1(3) . . ?
N1 C11 H11 124.0 . . ?
N2 C11 H11 124.0 . . ?
N2 C12 C13 112.3(3) . . ?
N2 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C18 118.0(3) . . ?
C14 C13 C12 119.3(3) . . ?
C18 C13 C12 122.8(3) . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 C19 124.1(3) . . ?
C17 C16 C19 117.2(3) . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
N3 C19 C16 116.4(3) . . ?
N3 C19 H19A 108.2 . . ?
C16 C19 H19A 108.2 . . ?
N3 C19 H19B 108.2 . . ?
C16 C19 H19B 108.2 . . ?
H19A C19 H19B 107.4 . . ?
C21 C20 N3 106.2(3) . . ?
C21 C20 H20 126.9 . . ?
N3 C20 H20 126.9 . . ?
C20 C21 N4 110.1(3) . . ?
C20 C21 H21 124.9 . . ?
N4 C21 H21 124.9 . . ?
N4 C22 N3 112.1(3) . . ?
N4 C22 H22 123.9 . . ?
N3 C22 H22 123.9 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C1 O2 5.4(3) . . . . ?
Mn1 O1 C1 C2 -174.6(2) . . . . ?
Mn1 O2 C1 O1 -5.1(3) . . . . ?
Mn1 O2 C1 C2 174.8(2) . . . . ?
O1 C1 C2 C7 -148.3(3) . . . . ?
O2 C1 C2 C7 31.7(4) . . . . ?
O1 C1 C2 C3 30.0(4) . . . . ?
O2 C1 C2 C3 -150.0(3) . . . . ?
C7 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C4 -178.0(3) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C2 C3 C4 C8 179.5(3) . . . . ?
C3 C4 C5 C6 -2.6(5) . . . . ?
C8 C4 C5 C6 179.8(3) . . . . ?
C4 C5 C6 C7 0.9(4) . . . . ?
C4 C5 C6 C6 179.5(3) . . . 2 ?
C3 C2 C7 C6 -2.0(5) . . . . ?
C1 C2 C7 C6 176.3(3) . . . . ?
C5 C6 C7 C2 1.4(4) . . . . ?
C6 C6 C7 C2 -177.2(3) 2 . . . ?
Mn1 O3 C8 O4 105.5(4) 2_556 . . . ?
Mn1 O3 C8 C4 -75.2(4) 2_556 . . . ?
Mn1 O4 C8 O3 -36.0(5) 1_545 . . . ?
Mn1 O4 C8 C4 144.6(2) 1_545 . . . ?
C3 C4 C8 O3 4.7(4) . . . . ?
C5 C4 C8 O3 -177.7(3) . . . . ?
C3 C4 C8 O4 -175.9(3) . . . . ?
C5 C4 C8 O4 1.7(4) . . . . ?
C11 N1 C9 C10 0.3(4) . . . . ?
Mn1 N1 C9 C10 -178.3(3) . . . . ?
N1 C9 C10 N2 0.2(5) . . . . ?
C11 N2 C10 C9 -0.7(4) . . . . ?
C12 N2 C10 C9 -171.4(3) . . . . ?
C9 N1 C11 N2 -0.8(4) . . . . ?
Mn1 N1 C11 N2 177.8(2) . . . . ?
C10 N2 C11 N1 1.0(4) . . . . ?
C12 N2 C11 N1 171.5(3) . . . . ?
C11 N2 C12 C13 -96.4(4) . . . . ?
C10 N2 C12 C13 72.5(5) . . . . ?
N2 C12 C13 C14 -165.4(3) . . . . ?
N2 C12 C13 C18 15.2(5) . . . . ?
C18 C13 C14 C15 -3.1(5) . . . . ?
C12 C13 C14 C15 177.6(3) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
C14 C15 C16 C17 1.1(5) . . . . ?
C14 C15 C16 C19 -172.1(3) . . . . ?
C15 C16 C17 C18 -0.9(5) . . . . ?
C19 C16 C17 C18 172.7(3) . . . . ?
C16 C17 C18 C13 -1.3(5) . . . . ?
C14 C13 C18 C17 3.3(5) . . . . ?
C12 C13 C18 C17 -177.4(3) . . . . ?
C22 N3 C19 C16 86.8(4) . . . . ?
C20 N3 C19 C16 -96.0(4) . . . . ?
C15 C16 C19 N3 -24.8(5) . . . . ?
C17 C16 C19 N3 161.9(3) . . . . ?
C22 N3 C20 C21 -0.4(4) . . . . ?
C19 N3 C20 C21 -178.1(3) . . . . ?
N3 C20 C21 N4 0.3(4) . . . . ?
C22 N4 C21 C20 0.0(4) . . . . ?
Mn1 N4 C21 C20 175.8(2) 1_664 . . . ?
C21 N4 C22 N3 -0.2(4) . . . . ?
Mn1 N4 C22 N3 -176.0(2) 1_664 . . . ?
C20 N3 C22 N4 0.4(4) . . . . ?
C19 N3 C22 N4 178.1(3) . . . . ?

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
C22 H22 O1 0.93 2.53 3.451(4) 168.6 2_665
O5 H5A O2 0.82 2.14 2.944(5) 165.2 1_655

_refine_diff_density_max         0.670
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.080

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sf171022a-19
_database_code_depnum_ccdc_archive 'CCDC 1586702'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H34 Mn2 N8 O8, 2(H2 O)'
_chemical_formula_sum            'C44 H38 Mn2 N8 O10'
_chemical_formula_weight         948.70

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   13.2825(7)
_cell_length_b                   16.7322(10)
_cell_length_c                   17.9666(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3993.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6212
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.65

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.706
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30864
_diffrn_reflns_av_unetI/netI     0.1988
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.434
_diffrn_reflns_theta_max         26.761
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8440
_reflns_number_gt                4381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0225P)²+1.8054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.50(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8440
_refine_ls_number_parameters     578
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1849
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.90174(7) 0.77914(7) 0.13056(7) 0.0218(3) Uani 1 1 d . . . . .
Mn2 Mn 0.81033(7) 0.78895(7) 0.36469(6) 0.0199(3) Uani 1 1 d . . . . .
O1 O 0.7531(3) 0.7756(4) 0.1704(3) 0.0346(15) Uani 1 1 d . . . . .
O2 O 0.6993(4) 0.8133(3) 0.2828(3) 0.0280(14) Uani 1 1 d . . . . .
O3 O 0.5053(3) 0.7217(4) -0.0291(3) 0.0312(15) Uani 1 1 d . . . . .
O4 O 0.3435(3) 0.7177(3) -0.0015(2) 0.0283(14) Uani 1 1 d . . . . .
O5 O 0.0148(3) 0.7712(4) 0.2135(3) 0.0351(17) Uani 1 1 d . . . . .
O6 O -0.0364(3) 0.7954(4) 0.3297(3) 0.0350(16) Uani 1 1 d . . . . .
O7 O 0.3639(3) 0.7333(3) 0.5147(3) 0.0243(14) Uani 1 1 d . . . . .
O8 O 0.2022(3) 0.7373(3) 0.5348(3) 0.0264(14) Uani 1 1 d . . . . .
O9 O 0.5342(4) 0.6667(4) 0.4565(3) 0.056(2) Uani 1 1 d D . . . .
H9A H 0.483049 0.688192 0.472429 0.083 Uiso 1 1 d DR U . . .
H9B H 0.581250 0.697159 0.464960 0.083 Uiso 1 1 d DR U . . .
O10 O 0.2005(4) 0.8326(3) 0.0544(3) 0.0595(19) Uani 1 1 d D . . . .
H10A H 0.139919 0.829426 0.045946 0.089 Uiso 1 1 d DR U . . .
H10B H 0.224364 0.790973 0.037976 0.089 Uiso 1 1 d DR U . . .
N1 N 0.9027(5) 0.6470(4) 0.1206(4) 0.0334(18) Uani 1 1 d . . . . .
N2 N 0.8566(5) 0.5266(4) 0.0860(4) 0.0323(19) Uani 1 1 d . . . . .
N3 N 0.4373(5) 0.4657(5) -0.0946(4) 0.032(2) Uani 1 1 d . . . . .
N4 N 0.4123(5) 0.5907(4) -0.1322(5) 0.0344(18) Uani 1 1 d . . . . .
N5 N 0.8023(5) 0.9179(4) 0.3948(4) 0.0243(17) Uani 1 1 d . . . . .
N6 N 0.8150(4) 1.0277(4) 0.4637(4) 0.0288(17) Uani 1 1 d . . . . .
N7 N 1.2333(4) 0.9622(4) 0.6715(4) 0.0294(18) Uani 1 1 d . . . . .
N8 N 1.2923(5) 0.8383(4) 0.6645(3) 0.0279(17) Uani 1 1 d . . . . .
C1 C 0.6852(5) 0.7862(5) 0.2178(4) 0.0195(18) Uani 1 1 d . . . . .
C2 C 0.5798(5) 0.7666(4) 0.1951(4) 0.0154(19) Uani 1 1 d . . . . .
C3 C 0.5576(5) 0.7488(4) 0.1216(4) 0.0166(19) Uani 1 1 d . . . . .
H3 H 0.609462 0.745915 0.086882 0.020 Uiso 1 1 calc R U . . .
C4 C 0.4595(5) 0.7353(4) 0.0990(4) 0.018(2) Uani 1 1 d . . . . .
C5 C 0.4354(5) 0.7236(5) 0.0177(4) 0.022(2) Uani 1 1 d . . . . .
C6 C 0.3824(5) 0.7385(4) 0.1512(4) 0.020(2) Uani 1 1 d . . . . .
H6 H 0.316519 0.729749 0.135729 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4010(5) 0.7546(4) 0.2269(4) 0.018(2) Uani 1 1 d . . . . .
C8 C 0.5011(5) 0.7683(4) 0.2471(4) 0.018(2) Uani 1 1 d . . . . .
H8 H 0.516108 0.778869 0.296697 0.022 Uiso 1 1 calc R U . . .
C9 C 0.3158(5) 0.7580(4) 0.2815(4) 0.019(2) Uani 1 1 d . . . . .
C10 C 0.3337(5) 0.7471(4) 0.3578(4) 0.0186(19) Uani 1 1 d . . . . .
H10 H 0.398575 0.736344 0.374521 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2558(5) 0.7524(4) 0.4079(4) 0.0179(19) Uani 1 1 d . . . . .
C12 C 0.1576(5) 0.7653(4) 0.3838(4) 0.0168(19) Uani 1 1 d . . . . .
H12 H 0.105420 0.768197 0.418235 0.020 Uiso 1 1 calc R U . . .
C13 C 0.1376(5) 0.7739(5) 0.3081(4) 0.0188(19) Uani 1 1 d . . . . .
C14 C 0.2173(5) 0.7694(4) 0.2573(4) 0.0188(19) Uani 1 1 d . . . . .
H14 H 0.204260 0.774084 0.206605 0.023 Uiso 1 1 calc R U . . .
C15 C 0.0298(5) 0.7819(5) 0.2814(4) 0.0225(19) Uani 1 1 d . . . . .
C16 C 0.2759(5) 0.7409(4) 0.4904(4) 0.0173(19) Uani 1 1 d . . . . .
C17 C 0.8325(6) 0.6037(5) 0.0892(5) 0.033(2) Uani 1 1 d . . . . .
H17 H 0.772420 0.624543 0.071070 0.040 Uiso 1 1 calc R U . . .
C18 C 0.9512(6) 0.5199(6) 0.1184(6) 0.043(3) Uani 1 1 d . . . . .
H18 H 0.988484 0.473370 0.124810 0.051 Uiso 1 1 calc R U . . .
C19 C 0.9775(6) 0.5938(6) 0.1383(5) 0.039(2) Uani 1 1 d . . . . .
H19 H 1.038134 0.607293 0.160966 0.047 Uiso 1 1 calc R U . . .
C20 C 0.8051(6) 0.4647(5) 0.0440(5) 0.046(3) Uani 1 1 d . . . . .
H20A H 0.838222 0.414104 0.053715 0.055 Uiso 1 1 calc R U . . .
H20B H 0.813016 0.476152 -0.008648 0.055 Uiso 1 1 calc R U . . .
C21 C 0.6948(6) 0.4551(5) 0.0601(5) 0.031(2) Uani 1 1 d . . . . .
C22 C 0.6591(7) 0.4549(5) 0.1314(6) 0.046(3) Uani 1 1 d . . . . .
H22 H 0.701923 0.468004 0.170503 0.055 Uiso 1 1 calc R U . . .
C23 C 0.5614(7) 0.4357(6) 0.1457(6) 0.058(3) Uani 1 1 d . . . . .
H23 H 0.537798 0.435812 0.194393 0.069 Uiso 1 1 calc R U . . .
C24 C 0.6295(6) 0.4383(5) 0.0028(5) 0.037(2) Uani 1 1 d . . . . .
H24 H 0.652851 0.439929 -0.045939 0.045 Uiso 1 1 calc R U . . .
C25 C 0.5303(6) 0.4190(5) 0.0160(5) 0.035(2) Uani 1 1 d . . . . .
C26 C 0.4983(7) 0.4165(5) 0.0888(6) 0.047(3) Uani 1 1 d . . . . .
H26 H 0.432394 0.401376 0.099319 0.056 Uiso 1 1 calc R U . . .
C27 C 0.4615(6) 0.3972(5) -0.0471(5) 0.040(3) Uani 1 1 d . . . . .
H27A H 0.493286 0.356103 -0.077075 0.048 Uiso 1 1 calc R U . . .
H27B H 0.399633 0.375254 -0.027044 0.048 Uiso 1 1 calc R U . . .
C28 C 0.4073(6) 0.4625(6) -0.1670(6) 0.041(3) Uani 1 1 d . . . . .
H28 H 0.398249 0.416578 -0.195373 0.050 Uiso 1 1 calc R U . . .
C29 C 0.3931(6) 0.5381(6) -0.1896(5) 0.039(2) Uani 1 1 d . . . . .
H29 H 0.373207 0.552938 -0.237236 0.047 Uiso 1 1 calc R U . . .
C30 C 0.4389(6) 0.5429(6) -0.0768(5) 0.037(3) Uani 1 1 d . . . . .
H30 H 0.456956 0.561512 -0.029903 0.044 Uiso 1 1 calc R U . . .
C31 C 0.7479(6) 0.9790(5) 0.3638(5) 0.037(2) Uani 1 1 d . . . . .
H31 H 0.711106 0.975018 0.319933 0.045 Uiso 1 1 calc R U . . .
C32 C 0.8419(5) 0.9496(5) 0.4549(5) 0.032(2) Uani 1 1 d . . . . .
H32 H 0.883510 0.922014 0.487638 0.039 Uiso 1 1 calc R U . . .
C33 C 0.7549(6) 1.0453(6) 0.4054(5) 0.043(3) Uani 1 1 d . . . . .
H33 H 0.724101 1.094199 0.395839 0.051 Uiso 1 1 calc R U . . .
C34 C 0.8503(6) 1.0845(5) 0.5203(5) 0.041(3) Uani 1 1 d . . . . .
H34A H 0.793038 1.112953 0.540764 0.049 Uiso 1 1 calc R U . . .
H34B H 0.894508 1.123379 0.497121 0.049 Uiso 1 1 calc R U . . .
C35 C 0.9060(6) 1.0428(5) 0.5824(5) 0.033(2) Uani 1 1 d . . . . .
C36 C 1.0093(6) 1.0533(5) 0.5914(5) 0.030(2) Uani 1 1 d . . . . .
H36 H 1.044257 1.086259 0.558742 0.036 Uiso 1 1 calc R U . . .
C37 C 1.0609(6) 1.0151(5) 0.6487(5) 0.031(2) Uani 1 1 d . . . . .
C38 C 1.0077(7) 0.9653(5) 0.6957(5) 0.038(3) Uani 1 1 d . . . . .
H38 H 1.041155 0.939357 0.734172 0.046 Uiso 1 1 calc R U . . .
C39 C 0.9060(7) 0.9536(6) 0.6863(5) 0.044(3) Uani 1 1 d . . . . .
H39 H 0.871760 0.918538 0.717514 0.053 Uiso 1 1 calc R U . . .
C40 C 0.8550(6) 0.9931(5) 0.6313(6) 0.043(2) Uani 1 1 d . . . . .
H40 H 0.785714 0.986683 0.626750 0.052 Uiso 1 1 calc R U . . .
C41 C 1.1718(5) 1.0347(5) 0.6595(5) 0.037(2) Uani 1 1 d . . . . .
H41A H 1.196459 1.062810 0.615970 0.044 Uiso 1 1 calc R U . . .
H41B H 1.179073 1.069960 0.702056 0.044 Uiso 1 1 calc R U . . .
C42 C 1.3273(6) 0.9636(6) 0.7032(4) 0.036(2) Uani 1 1 d . . . . .
H42 H 1.360862 1.007335 0.723401 0.043 Uiso 1 1 calc R U . . .
C43 C 1.3603(6) 0.8872(6) 0.6986(4) 0.037(3) Uani 1 1 d . . . . .
H43 H 1.422249 0.869999 0.716678 0.044 Uiso 1 1 calc R U . . .
C44 C 1.2162(6) 0.8868(5) 0.6492(4) 0.028(2) Uani 1 1 d . . . . .
H44 H 1.157362 0.870512 0.625516 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 2.102(5) . ?
Mn1 O5 2.119(5) 1_655 ?
Mn1 N4 2.183(7) 4_565 ?
Mn1 N1 2.218(7) . ?
Mn1 O3 2.284(5) 4_565 ?
Mn1 O4 2.445(5) 4_565 ?
Mn2 O2 2.122(5) . ?
Mn2 O6 2.133(5) 1_655 ?
Mn2 N8 2.205(7) 4_466 ?
Mn2 N5 2.227(6) . ?
Mn2 O7 2.311(5) 4_566 ?
Mn2 O8 2.349(5) 4_566 ?
O1 C1 1.253(7) . ?
O2 C1 1.266(8) . ?
O3 C5 1.254(8) . ?
O4 C5 1.272(7) . ?
O5 C15 1.249(8) . ?
O6 C15 1.256(8) . ?
O7 C16 1.254(7) . ?
O8 C16 1.264(8) . ?
O9 H9A 0.8203 . ?
O9 H9B 0.8208 . ?
O10 H10A 0.8209 . ?
O10 H10B 0.8205 . ?
N1 C17 1.309(9) . ?
N1 C19 1.372(9) . ?
N2 C17 1.330(9) . ?
N2 C18 1.389(9) . ?
N2 C20 1.453(9) . ?
N3 C30 1.330(10) . ?
N3 C28 1.361(10) . ?
N3 C27 1.465(10) . ?
N4 C30 1.324(10) . ?
N4 C29 1.380(10) . ?
N5 C32 1.313(9) . ?
N5 C31 1.371(9) . ?
N6 C33 1.350(9) . ?
N6 C32 1.364(9) . ?
N6 C34 1.468(9) . ?
N7 C44 1.342(9) . ?
N7 C42 1.372(9) . ?
N7 C41 1.479(9) . ?
N8 C44 1.327(9) . ?
N8 C43 1.364(9) . ?
C1 C2 1.496(9) . ?
C2 C3 1.386(9) . ?
C2 C8 1.402(9) . ?
C3 C4 1.384(8) . ?
C3 H3 0.9300 . ?
C4 C6 1.390(9) . ?
C4 C5 1.509(9) . ?
C6 C7 1.408(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(10) . ?
C7 C9 1.497(9) . ?
C8 H8 0.9300 . ?
C9 C14 1.392(9) . ?
C9 C10 1.403(9) . ?
C10 C11 1.375(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(8) . ?
C11 C16 1.520(9) . ?
C12 C13 1.393(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.401(9) . ?
C13 C15 1.515(9) . ?
C14 H14 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.334(11) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.502(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.366(11) . ?
C21 C24 1.375(10) . ?
C22 C23 1.361(11) . ?
C22 H22 0.9300 . ?
C23 C26 1.361(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(11) . ?
C25 C27 1.501(11) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.342(12) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C33 1.341(10) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C35 1.511(11) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C40 1.386(11) . ?
C35 C36 1.393(10) . ?
C36 C37 1.392(10) . ?
C36 H36 0.9300 . ?
C37 C38 1.380(10) . ?
C37 C41 1.521(10) . ?
C38 C39 1.375(11) . ?
C38 H38 0.9300 . ?
C39 C40 1.369(12) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.355(11) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?

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 O5 115.1(2) . 1_655 ?
O1 Mn1 N4 94.8(2) . 4_565 ?
O5 Mn1 N4 90.4(3) 1_655 4_565 ?
O1 Mn1 N1 90.3(2) . . ?
O5 Mn1 N1 89.5(3) 1_655 . ?
N4 Mn1 N1 174.4(3) 4_565 . ?
O1 Mn1 O3 146.92(19) . 4_565 ?
O5 Mn1 O3 97.69(18) 1_655 4_565 ?
N4 Mn1 O3 88.7(3) 4_565 4_565 ?
N1 Mn1 O3 85.7(2) . 4_565 ?
O1 Mn1 O4 91.51(18) . 4_565 ?
O5 Mn1 O4 153.16(17) 1_655 4_565 ?
N4 Mn1 O4 90.7(2) 4_565 4_565 ?
N1 Mn1 O4 86.9(2) . 4_565 ?
O3 Mn1 O4 55.53(15) 4_565 4_565 ?
O2 Mn2 O6 116.7(2) . 1_655 ?
O2 Mn2 N8 86.9(2) . 4_466 ?
O6 Mn2 N8 94.7(2) 1_655 4_466 ?
O2 Mn2 N5 87.1(2) . . ?
O6 Mn2 N5 93.9(2) 1_655 . ?
N8 Mn2 N5 171.0(2) 4_466 . ?
O2 Mn2 O7 153.47(17) . 4_566 ?
O6 Mn2 O7 89.47(17) 1_655 4_566 ?
N8 Mn2 O7 95.8(2) 4_466 4_566 ?
N5 Mn2 O7 86.7(2) . 4_566 ?
O2 Mn2 O8 98.25(18) . 4_566 ?
O6 Mn2 O8 145.06(18) 1_655 4_566 ?
N8 Mn2 O8 86.3(2) 4_466 4_566 ?
N5 Mn2 O8 88.0(2) . 4_566 ?
O7 Mn2 O8 55.77(16) 4_566 4_566 ?
C1 O1 Mn1 154.6(5) . . ?
C1 O2 Mn2 132.3(5) . . ?
C5 O3 Mn1 95.1(4) . 4_465 ?
C5 O4 Mn1 87.2(4) . 4_465 ?
C15 O5 Mn1 142.3(5) . 1_455 ?
C15 O6 Mn2 149.6(5) . 1_455 ?
C16 O7 Mn2 93.1(4) . 4_466 ?
C16 O8 Mn2 91.1(4) . 4_466 ?
H9A O9 H9B 107.1 . . ?
H10A O10 H10B 104.9 . . ?
C17 N1 C19 104.8(7) . . ?
C17 N1 Mn1 125.6(6) . . ?
C19 N1 Mn1 129.3(6) . . ?
C17 N2 C18 106.1(7) . . ?
C17 N2 C20 126.9(7) . . ?
C18 N2 C20 125.8(8) . . ?
C30 N3 C28 105.8(8) . . ?
C30 N3 C27 128.0(8) . . ?
C28 N3 C27 126.1(9) . . ?
C30 N4 C29 103.0(7) . . ?
C30 N4 Mn1 127.6(7) . 4_465 ?
C29 N4 Mn1 129.4(7) . 4_465 ?
C32 N5 C31 104.1(7) . . ?
C32 N5 Mn2 124.9(6) . . ?
C31 N5 Mn2 130.5(6) . . ?
C33 N6 C32 105.9(7) . . ?
C33 N6 C34 125.8(7) . . ?
C32 N6 C34 128.1(7) . . ?
C44 N7 C42 107.2(7) . . ?
C44 N7 C41 129.3(7) . . ?
C42 N7 C41 123.3(8) . . ?
C44 N8 C43 103.3(6) . . ?
C44 N8 Mn2 128.6(5) . 4_566 ?
C43 N8 Mn2 127.9(6) . 4_566 ?
O1 C1 O2 124.9(7) . . ?
O1 C1 C2 117.1(6) . . ?
O2 C1 C2 118.0(6) . . ?
C3 C2 C8 118.8(6) . . ?
C3 C2 C1 120.4(6) . . ?
C8 C2 C1 120.7(6) . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C6 119.3(7) . . ?
C3 C4 C5 120.3(6) . . ?
C6 C4 C5 120.2(6) . . ?
O3 C5 O4 121.8(7) . . ?
O3 C5 C4 119.7(6) . . ?
O4 C5 C4 118.4(6) . . ?
C4 C6 C7 122.0(7) . . ?
C4 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 116.6(6) . . ?
C8 C7 C9 122.9(6) . . ?
C6 C7 C9 120.5(6) . . ?
C7 C8 C2 122.2(7) . . ?
C7 C8 H8 118.9 . . ?
C2 C8 H8 118.9 . . ?
C14 C9 C10 118.8(7) . . ?
C14 C9 C7 120.7(6) . . ?
C10 C9 C7 120.4(6) . . ?
C11 C10 C9 120.2(6) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.9(7) . . ?
C10 C11 C16 119.9(6) . . ?
C12 C11 C16 119.2(6) . . ?
C11 C12 C13 119.9(6) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 119.1(6) . . ?
C12 C13 C15 119.9(6) . . ?
C14 C13 C15 120.8(6) . . ?
C9 C14 C13 120.9(7) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
O5 C15 O6 126.0(7) . . ?
O5 C15 C13 116.6(6) . . ?
O6 C15 C13 117.3(7) . . ?
O7 C16 O8 119.9(7) . . ?
O7 C16 C11 121.0(6) . . ?
O8 C16 C11 119.1(6) . . ?
N1 C17 N2 112.6(7) . . ?
N1 C17 H17 123.7 . . ?
N2 C17 H17 123.7 . . ?
C19 C18 N2 105.9(8) . . ?
C19 C18 H18 127.0 . . ?
N2 C18 H18 127.0 . . ?
C18 C19 N1 110.5(8) . . ?
C18 C19 H19 124.8 . . ?
N1 C19 H19 124.8 . . ?
N2 C20 C21 115.8(7) . . ?
N2 C20 H20A 108.3 . . ?
C21 C20 H20A 108.3 . . ?
N2 C20 H20B 108.3 . . ?
C21 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C24 118.8(8) . . ?
C22 C21 C20 121.3(8) . . ?
C24 C21 C20 119.5(8) . . ?
C23 C22 C21 120.5(9) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C26 C23 C22 120.2(10) . . ?
C26 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C21 C24 C25 121.6(8) . . ?
C21 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C26 C25 C24 117.8(9) . . ?
C26 C25 C27 121.5(8) . . ?
C24 C25 C27 120.6(8) . . ?
C23 C26 C25 121.0(9) . . ?
C23 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
N3 C27 C25 112.6(7) . . ?
N3 C27 H27A 109.1 . . ?
C25 C27 H27A 109.1 . . ?
N3 C27 H27B 109.1 . . ?
C25 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C29 C28 N3 107.0(9) . . ?
C29 C28 H28 126.5 . . ?
N3 C28 H28 126.5 . . ?
C28 C29 N4 110.4(8) . . ?
C28 C29 H29 124.8 . . ?
N4 C29 H29 124.8 . . ?
N4 C30 N3 113.7(8) . . ?
N4 C30 H30 123.2 . . ?
N3 C30 H30 123.2 . . ?
C33 C31 N5 110.8(8) . . ?
C33 C31 H31 124.6 . . ?
N5 C31 H31 124.6 . . ?
N5 C32 N6 112.2(7) . . ?
N5 C32 H32 123.9 . . ?
N6 C32 H32 123.9 . . ?
C31 C33 N6 107.0(8) . . ?
C31 C33 H33 126.5 . . ?
N6 C33 H33 126.5 . . ?
N6 C34 C35 111.7(7) . . ?
N6 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
N6 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
C40 C35 C36 118.9(8) . . ?
C40 C35 C34 120.4(8) . . ?
C36 C35 C34 120.7(8) . . ?
C35 C36 C37 120.9(8) . . ?
C35 C36 H36 119.6 . . ?
C37 C36 H36 119.6 . . ?
C38 C37 C36 118.5(8) . . ?
C38 C37 C41 123.2(8) . . ?
C36 C37 C41 118.2(8) . . ?
C39 C38 C37 121.0(9) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C38 C39 C40 120.3(9) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C39 C40 C35 120.3(8) . . ?
C39 C40 H40 119.8 . . ?
C35 C40 H40 119.8 . . ?
N7 C41 C37 112.1(7) . . ?
N7 C41 H41A 109.2 . . ?
C37 C41 H41A 109.2 . . ?
N7 C41 H41B 109.2 . . ?
C37 C41 H41B 109.2 . . ?
H41A C41 H41B 107.9 . . ?
C43 C42 N7 104.6(8) . . ?
C43 C42 H42 127.7 . . ?
N7 C42 H42 127.7 . . ?
C42 C43 N8 112.3(7) . . ?
C42 C43 H43 123.8 . . ?
N8 C43 H43 123.8 . . ?
N8 C44 N7 112.5(7) . . ?
N8 C44 H44 123.7 . . ?
N7 C44 H44 123.7 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C1 O2 -1.9(19) . . . . ?
Mn1 O1 C1 C2 177.1(9) . . . . ?
Mn2 O2 C1 O1 -43.5(11) . . . . ?
Mn2 O2 C1 C2 137.6(6) . . . . ?
O1 C1 C2 C3 -9.2(11) . . . . ?
O2 C1 C2 C3 169.9(7) . . . . ?
O1 C1 C2 C8 172.9(7) . . . . ?
O2 C1 C2 C8 -8.1(11) . . . . ?
C8 C2 C3 C4 1.9(11) . . . . ?
C1 C2 C3 C4 -176.1(7) . . . . ?
C2 C3 C4 C6 -0.9(11) . . . . ?
C2 C3 C4 C5 174.3(7) . . . . ?
Mn1 O3 C5 O4 5.9(9) 4_465 . . . ?
Mn1 O3 C5 C4 -172.5(6) 4_465 . . . ?
Mn1 O4 C5 O3 -5.5(8) 4_465 . . . ?
Mn1 O4 C5 C4 172.9(7) 4_465 . . . ?
C3 C4 C5 O3 4.0(12) . . . . ?
C6 C4 C5 O3 179.2(7) . . . . ?
C3 C4 C5 O4 -174.5(7) . . . . ?
C6 C4 C5 O4 0.7(12) . . . . ?
C3 C4 C6 C7 -0.5(11) . . . . ?
C5 C4 C6 C7 -175.7(7) . . . . ?
C4 C6 C7 C8 0.8(11) . . . . ?
C4 C6 C7 C9 179.7(7) . . . . ?
C6 C7 C8 C2 0.3(11) . . . . ?
C9 C7 C8 C2 -178.6(7) . . . . ?
C3 C2 C8 C7 -1.6(12) . . . . ?
C1 C2 C8 C7 176.4(7) . . . . ?
C8 C7 C9 C14 159.5(7) . . . . ?
C6 C7 C9 C14 -19.4(12) . . . . ?
C8 C7 C9 C10 -22.7(12) . . . . ?
C6 C7 C9 C10 158.5(6) . . . . ?
C14 C9 C10 C11 -3.8(11) . . . . ?
C7 C9 C10 C11 178.3(7) . . . . ?
C9 C10 C11 C12 2.6(11) . . . . ?
C9 C10 C11 C16 -179.7(7) . . . . ?
C10 C11 C12 C13 -0.7(11) . . . . ?
C16 C11 C12 C13 -178.4(7) . . . . ?
C11 C12 C13 C14 0.0(11) . . . . ?
C11 C12 C13 C15 175.5(7) . . . . ?
C10 C9 C14 C13 3.1(12) . . . . ?
C7 C9 C14 C13 -179.0(7) . . . . ?
C12 C13 C14 C9 -1.3(12) . . . . ?
C15 C13 C14 C9 -176.7(7) . . . . ?
Mn1 O5 C15 O6 9.9(17) 1_455 . . . ?
Mn1 O5 C15 C13 -173.0(6) 1_455 . . . ?
Mn2 O6 C15 O5 21.8(19) 1_455 . . . ?
Mn2 O6 C15 C13 -155.2(8) 1_455 . . . ?
C12 C13 C15 O5 -164.2(8) . . . . ?
C14 C13 C15 O5 11.2(13) . . . . ?
C12 C13 C15 O6 13.0(12) . . . . ?
C14 C13 C15 O6 -171.5(8) . . . . ?
Mn2 O7 C16 O8 2.5(8) 4_466 . . . ?
Mn2 O7 C16 C11 -176.0(6) 4_466 . . . ?
Mn2 O8 C16 O7 -2.4(7) 4_466 . . . ?
Mn2 O8 C16 C11 176.1(6) 4_466 . . . ?
C10 C11 C16 O7 6.1(11) . . . . ?
C12 C11 C16 O7 -176.2(7) . . . . ?
C10 C11 C16 O8 -172.4(7) . . . . ?
C12 C11 C16 O8 5.3(11) . . . . ?
C19 N1 C17 N2 0.5(10) . . . . ?
Mn1 N1 C17 N2 175.1(5) . . . . ?
C18 N2 C17 N1 -0.1(10) . . . . ?
C20 N2 C17 N1 -168.5(7) . . . . ?
C17 N2 C18 C19 -0.4(10) . . . . ?
C20 N2 C18 C19 168.2(8) . . . . ?
N2 C18 C19 N1 0.7(11) . . . . ?
C17 N1 C19 C18 -0.8(10) . . . . ?
Mn1 N1 C19 C18 -175.0(6) . . . . ?
C17 N2 C20 C21 -56.2(12) . . . . ?
C18 N2 C20 C21 137.5(8) . . . . ?
N2 C20 C21 C22 -44.5(12) . . . . ?
N2 C20 C21 C24 142.1(8) . . . . ?
C24 C21 C22 C23 2.2(14) . . . . ?
C20 C21 C22 C23 -171.3(8) . . . . ?
C21 C22 C23 C26 0.1(15) . . . . ?
C22 C21 C24 C25 -2.0(13) . . . . ?
C20 C21 C24 C25 171.6(8) . . . . ?
C21 C24 C25 C26 -0.4(13) . . . . ?
C21 C24 C25 C27 -177.3(8) . . . . ?
C22 C23 C26 C25 -2.6(16) . . . . ?
C24 C25 C26 C23 2.7(14) . . . . ?
C27 C25 C26 C23 179.5(9) . . . . ?
C30 N3 C27 C25 -24.3(12) . . . . ?
C28 N3 C27 C25 156.4(8) . . . . ?
C26 C25 C27 N3 113.1(10) . . . . ?
C24 C25 C27 N3 -70.2(10) . . . . ?
C30 N3 C28 C29 0.6(10) . . . . ?
C27 N3 C28 C29 -180.0(8) . . . . ?
N3 C28 C29 N4 -0.9(11) . . . . ?
C30 N4 C29 C28 0.8(10) . . . . ?
Mn1 N4 C29 C28 -179.0(6) 4_465 . . . ?
C29 N4 C30 N3 -0.4(10) . . . . ?
Mn1 N4 C30 N3 179.4(5) 4_465 . . . ?
C28 N3 C30 N4 -0.2(10) . . . . ?
C27 N3 C30 N4 -179.6(7) . . . . ?
C32 N5 C31 C33 -0.5(9) . . . . ?
Mn2 N5 C31 C33 171.7(6) . . . . ?
C31 N5 C32 N6 0.3(9) . . . . ?
Mn2 N5 C32 N6 -172.5(5) . . . . ?
C33 N6 C32 N5 0.1(9) . . . . ?
C34 N6 C32 N5 -174.8(7) . . . . ?
N5 C31 C33 N6 0.5(10) . . . . ?
C32 N6 C33 C31 -0.4(9) . . . . ?
C34 N6 C33 C31 174.6(7) . . . . ?
C33 N6 C34 C35 173.2(7) . . . . ?
C32 N6 C34 C35 -12.9(11) . . . . ?
N6 C34 C35 C40 -68.7(10) . . . . ?
N6 C34 C35 C36 111.2(9) . . . . ?
C40 C35 C36 C37 -0.3(12) . . . . ?
C34 C35 C36 C37 179.8(7) . . . . ?
C35 C36 C37 C38 1.2(12) . . . . ?
C35 C36 C37 C41 -174.8(8) . . . . ?
C36 C37 C38 C39 0.0(13) . . . . ?
C41 C37 C38 C39 175.7(8) . . . . ?
C37 C38 C39 C40 -2.0(14) . . . . ?
C38 C39 C40 C35 2.8(14) . . . . ?
C36 C35 C40 C39 -1.7(13) . . . . ?
C34 C35 C40 C39 178.1(8) . . . . ?
C44 N7 C41 C37 26.2(12) . . . . ?
C42 N7 C41 C37 -160.7(7) . . . . ?
C38 C37 C41 N7 49.1(11) . . . . ?
C36 C37 C41 N7 -135.1(8) . . . . ?
C44 N7 C42 C43 -0.9(9) . . . . ?
C41 N7 C42 C43 -175.3(7) . . . . ?
N7 C42 C43 N8 1.0(10) . . . . ?
C44 N8 C43 C42 -0.7(9) . . . . ?
Mn2 N8 C43 C42 175.5(5) 4_566 . . . ?
C43 N8 C44 N7 0.1(9) . . . . ?
Mn2 N8 C44 N7 -176.1(5) 4_566 . . . ?
C42 N7 C44 N8 0.5(9) . . . . ?
C41 N7 C44 N8 174.5(7) . . . . ?

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
C44 H44 O9 0.93 2.29 3.201(9) 167.0 4_566
C41 H41A O10 0.97 2.48 3.372(10) 152.6 2_675
C34 H34A O4 0.97 2.62 3.422(9) 140.3 3_655
C32 H32 O7 0.93 2.61 3.122(10) 115.1 4_566
C27 H27B O8 0.97 2.57 3.458(9) 152.1 2_564
C17 H17 O10 0.93 2.55 3.297(10) 137.4 4_565
O10 H10B O4 0.82 2.12 2.883(8) 153.9 .
O10 H10A O3 0.82 2.00 2.785(7) 158.4 4_465
O9 H9B O8 0.82 1.94 2.754(7) 168.4 4_566
O9 H9A O7 0.82 1.91 2.730(7) 176.2 .

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.096

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zs63-2_sq
_database_code_depnum_ccdc_archive 'CCDC 1586701'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 Mn N4 O4,C3H7NO,H2O'
_chemical_formula_sum            'C23 H20 Mn N5 O5'
_chemical_formula_weight         501.38

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.109(5)
_cell_length_b                   10.461(5)
_cell_length_c                   12.102(6)
_cell_angle_alpha                67.592(7)
_cell_angle_beta                 68.056(7)
_cell_angle_gamma                84.450(7)
_cell_volume                     1095.9(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3078
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.2

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.633
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14956
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.956
_diffrn_reflns_theta_max         28.206
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5375
_reflns_number_gt                4142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.0371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5375
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.14878(13) 0.55620(13) 0.59924(12) 0.0296(3) Uani 1 1 d . . . . .
Mn1 Mn -0.36999(3) 0.50349(3) 0.62047(3) 0.02384(9) Uani 1 1 d . . . . .
O1 O -0.30788(13) 0.46960(15) 0.79522(13) 0.0360(3) Uani 1 1 d . . . . .
O3 O 0.34876(14) 0.40387(15) 0.57318(12) 0.0353(3) Uani 1 1 d . . . . .
O4 O 0.42072(13) 0.40816(14) 0.72326(12) 0.0314(3) Uani 1 1 d . . . . .
N1 N -0.28502(17) 0.29497(17) 0.62171(17) 0.0341(4) Uani 1 1 d . . . . .
N2 N -0.14106(17) 0.12320(17) 0.64828(19) 0.0391(4) Uani 1 1 d . . . . .
N3 N 0.35809(18) -0.15732(18) 0.66398(18) 0.0379(4) Uani 1 1 d . . . . .
N4 N 0.52808(17) -0.30498(18) 0.64577(17) 0.0352(4) Uani 1 1 d . . . . .
C1 C -0.18174(18) 0.50792(19) 0.71935(18) 0.0250(4) Uani 1 1 d . . . . .
C2 C -0.06510(18) 0.49356(19) 0.77120(17) 0.0247(4) Uani 1 1 d . . . . .
C3 C -0.09322(18) 0.5037(2) 0.88879(17) 0.0283(4) Uani 1 1 d . . . . .
H3 H -0.185734 0.518336 0.936094 0.034 Uiso 1 1 calc R U . . .
C4 C 0.01448(18) 0.4924(2) 0.93775(17) 0.0267(4) Uani 1 1 d . . . . .
C5 C 0.15067(18) 0.4647(2) 0.86584(17) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.224162 0.455898 0.896512 0.033 Uiso 1 1 calc R U . . .
C6 C 0.17922(18) 0.45006(19) 0.74965(17) 0.0238(4) Uani 1 1 d . . . . .
C7 C 0.32749(18) 0.41851(18) 0.67617(17) 0.0241(4) Uani 1 1 d . . . . .
C8 C 0.07112(18) 0.46703(18) 0.70123(17) 0.0231(4) Uani 1 1 d . . . . .
H8 H 0.090027 0.460628 0.622222 0.028 Uiso 1 1 calc R U . . .
C9 C -0.3634(2) 0.1722(2) 0.6840(3) 0.0590(7) Uani 1 1 d . . . . .
H9 H -0.462246 0.163258 0.710817 0.071 Uiso 1 1 calc R U . . .
C10 C -0.2773(2) 0.0657(3) 0.7012(3) 0.0704(9) Uani 1 1 d . . . . .
H10 H -0.304768 -0.028118 0.741061 0.085 Uiso 1 1 calc R U . . .
C11 C -0.1512(2) 0.2612(2) 0.60114(19) 0.0328(4) Uani 1 1 d . . . . .
H11 H -0.073506 0.324948 0.559206 0.039 Uiso 1 1 calc R U . . .
C12 C -0.0125(2) 0.0518(2) 0.6486(2) 0.0366(5) Uani 1 1 d . . . . .
C13 C 0.1030(2) 0.1200(2) 0.6388(3) 0.0506(6) Uani 1 1 d . . . . .
H13 H 0.098181 0.212127 0.630924 0.061 Uiso 1 1 calc R U . . .
C14 C 0.2269(2) 0.0516(2) 0.6408(3) 0.0525(7) Uani 1 1 d . . . . .
H14 H 0.306274 0.098255 0.631911 0.063 Uiso 1 1 calc R U . . .
C15 C 0.2321(2) -0.0850(2) 0.6558(2) 0.0371(5) Uani 1 1 d . . . . .
C16 C 0.1169(2) -0.1534(2) 0.6656(3) 0.0517(6) Uani 1 1 d . . . . .
H16 H 0.121183 -0.246154 0.675349 0.062 Uiso 1 1 calc R U . . .
C17 C -0.0061(2) -0.0839(2) 0.6608(3) 0.0551(7) Uani 1 1 d . . . . .
H17 H -0.083951 -0.129515 0.665895 0.066 Uiso 1 1 calc R U . . .
C18 C 0.4332(3) -0.1516(3) 0.7349(3) 0.0777(10) Uani 1 1 d . . . . .
H18 H 0.416361 -0.095790 0.782471 0.093 Uiso 1 1 calc R U . . .
C19 C 0.5364(3) -0.2422(3) 0.7228(3) 0.0693(9) Uani 1 1 d . . . . .
H19 H 0.603702 -0.259338 0.761516 0.083 Uiso 1 1 calc R U . . .
C20 C 0.4190(2) -0.2519(2) 0.6137(2) 0.0387(5) Uani 1 1 d . . . . .
H20 H 0.387308 -0.277237 0.561594 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O2 C1 1.261(2) . ?
O2 Mn1 2.2522(16) . ?
Mn1 O3 2.1001(17) 2_566 ?
Mn1 O4 2.1245(16) 1_455 ?
Mn1 N4 2.2366(18) 1_465 ?
Mn1 N1 2.2624(19) . ?
Mn1 O1 2.3173(17) . ?
Mn1 C1 2.6110(19) . ?
O1 C1 1.254(2) . ?
O3 C7 1.250(2) . ?
O4 C7 1.249(2) . ?
N1 C11 1.319(2) . ?
N1 C9 1.363(3) . ?
N2 C11 1.344(2) . ?
N2 C10 1.369(3) . ?
N2 C12 1.436(2) . ?
N3 C20 1.338(2) . ?
N3 C18 1.360(3) . ?
N3 C15 1.434(2) . ?
N4 C20 1.308(2) . ?
N4 C19 1.358(3) . ?
C1 C2 1.501(2) . ?
C2 C3 1.387(2) . ?
C2 C8 1.387(2) . ?
C3 C4 1.398(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(2) . ?
C4 C4 1.492(3) 2_567 ?
C5 C6 1.392(2) . ?
C5 H5 0.9300 . ?
C6 C8 1.390(2) . ?
C6 C7 1.509(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.347(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.368(3) . ?
C12 C13 1.371(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(3) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.346(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
C1 O2 Mn1 91.56(10) . . ?
O3 Mn1 O4 106.29(5) 2_566 1_455 ?
O3 Mn1 N4 87.58(6) 2_566 1_465 ?
O4 Mn1 N4 85.59(6) 1_455 1_465 ?
O3 Mn1 O2 98.87(5) 2_566 . ?
O4 Mn1 O2 154.75(5) 1_455 . ?
N4 Mn1 O2 97.73(6) 1_465 . ?
O3 Mn1 N1 98.79(6) 2_566 . ?
O4 Mn1 N1 88.96(6) 1_455 . ?
N4 Mn1 N1 172.58(6) 1_465 . ?
O2 Mn1 N1 85.10(6) . . ?
O3 Mn1 O1 154.59(6) 2_566 . ?
O4 Mn1 O1 97.99(6) 1_455 . ?
N4 Mn1 O1 86.92(6) 1_465 . ?
O2 Mn1 O1 57.44(5) . . ?
N1 Mn1 O1 88.86(6) . . ?
O3 Mn1 C1 127.55(6) 2_566 . ?
O4 Mn1 C1 126.14(6) 1_455 . ?
N4 Mn1 C1 94.53(6) 1_465 . ?
O2 Mn1 C1 28.87(5) . . ?
N1 Mn1 C1 84.62(6) . . ?
O1 Mn1 C1 28.70(5) . . ?
C1 O1 Mn1 88.76(11) . . ?
C7 O3 Mn1 147.91(13) . 2_566 ?
C7 O4 Mn1 125.12(12) . 1_655 ?
C11 N1 C9 105.21(17) . . ?
C11 N1 Mn1 125.84(13) . . ?
C9 N1 Mn1 125.61(14) . . ?
C11 N2 C10 106.61(17) . . ?
C11 N2 C12 126.11(17) . . ?
C10 N2 C12 127.20(18) . . ?
C20 N3 C18 105.82(17) . . ?
C20 N3 C15 127.87(18) . . ?
C18 N3 C15 126.10(18) . . ?
C20 N4 C19 104.76(17) . . ?
C20 N4 Mn1 124.37(14) . 1_645 ?
C19 N4 Mn1 128.84(14) . 1_645 ?
O1 C1 O2 121.71(16) . . ?
O1 C1 C2 119.86(16) . . ?
O2 C1 C2 118.41(16) . . ?
O1 C1 Mn1 62.54(10) . . ?
O2 C1 Mn1 59.57(9) . . ?
C2 C1 Mn1 172.03(12) . . ?
C3 C2 C8 120.16(16) . . ?
C3 C2 C1 120.68(15) . . ?
C8 C2 C1 119.15(16) . . ?
C2 C3 C4 121.44(16) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 117.28(16) . . ?
C3 C4 C4 121.55(19) . 2_567 ?
C5 C4 C4 121.16(19) . 2_567 ?
C6 C5 C4 121.80(16) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C8 C6 C5 119.52(16) . . ?
C8 C6 C7 120.56(16) . . ?
C5 C6 C7 119.91(15) . . ?
O4 C7 O3 124.42(16) . . ?
O4 C7 C6 117.38(16) . . ?
O3 C7 C6 118.19(15) . . ?
C2 C8 C6 119.73(16) . . ?
C2 C8 H8 120.1 . . ?
C6 C8 H8 120.1 . . ?
C10 C9 N1 110.3(2) . . ?
C10 C9 H9 124.9 . . ?
N1 C9 H9 124.9 . . ?
C9 C10 N2 106.3(2) . . ?
C9 C10 H10 126.9 . . ?
N2 C10 H10 126.9 . . ?
N1 C11 N2 111.63(18) . . ?
N1 C11 H11 124.2 . . ?
N2 C11 H11 124.2 . . ?
C17 C12 C13 120.22(19) . . ?
C17 C12 N2 120.25(19) . . ?
C13 C12 N2 119.52(18) . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.48(19) . . ?
C14 C15 N3 119.57(19) . . ?
C16 C15 N3 119.94(19) . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 119.8(2) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 N3 106.7(2) . . ?
C19 C18 H18 126.7 . . ?
N3 C18 H18 126.7 . . ?
C18 C19 N4 110.1(2) . . ?
C18 C19 H19 125.0 . . ?
N4 C19 H19 125.0 . . ?
N4 C20 N3 112.66(18) . . ?
N4 C20 H20 123.7 . . ?
N3 C20 H20 123.7 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C1 O2 7.20(18) . . . . ?
Mn1 O1 C1 C2 -171.33(15) . . . . ?
Mn1 O2 C1 O1 -7.41(18) . . . . ?
Mn1 O2 C1 C2 171.14(14) . . . . ?
O1 C1 C2 C3 -31.2(3) . . . . ?
O2 C1 C2 C3 150.26(18) . . . . ?
O1 C1 C2 C8 147.50(18) . . . . ?
O2 C1 C2 C8 -31.1(3) . . . . ?
C8 C2 C3 C4 2.2(3) . . . . ?
C1 C2 C3 C4 -179.16(17) . . . . ?
C2 C3 C4 C5 -2.6(3) . . . . ?
C2 C3 C4 C4 178.1(2) . . . 2_567 ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C4 C5 C6 179.9(2) 2_567 . . . ?
C4 C5 C6 C8 1.9(3) . . . . ?
C4 C5 C6 C7 -179.26(17) . . . . ?
Mn1 O4 C7 O3 47.1(2) 1_655 . . . ?
Mn1 O4 C7 C6 -133.24(14) 1_655 . . . ?
Mn1 O3 C7 O4 -108.7(2) 2_566 . . . ?
Mn1 O3 C7 C6 71.7(3) 2_566 . . . ?
C8 C6 C7 O4 178.11(17) . . . . ?
C5 C6 C7 O4 -0.8(3) . . . . ?
C8 C6 C7 O3 -2.2(3) . . . . ?
C5 C6 C7 O3 178.90(17) . . . . ?
C3 C2 C8 C6 0.3(3) . . . . ?
C1 C2 C8 C6 -178.39(17) . . . . ?
C5 C6 C8 C2 -2.2(3) . . . . ?
C7 C6 C8 C2 178.86(16) . . . . ?
C11 N1 C9 C10 0.3(3) . . . . ?
Mn1 N1 C9 C10 -159.9(2) . . . . ?
N1 C9 C10 N2 0.0(4) . . . . ?
C11 N2 C10 C9 -0.3(3) . . . . ?
C12 N2 C10 C9 176.5(2) . . . . ?
C9 N1 C11 N2 -0.5(3) . . . . ?
Mn1 N1 C11 N2 159.64(14) . . . . ?
C10 N2 C11 N1 0.6(3) . . . . ?
C12 N2 C11 N1 -176.36(19) . . . . ?
C11 N2 C12 C17 -159.3(2) . . . . ?
C10 N2 C12 C17 24.4(4) . . . . ?
C11 N2 C12 C13 21.8(3) . . . . ?
C10 N2 C12 C13 -154.5(3) . . . . ?
C17 C12 C13 C14 0.3(4) . . . . ?
N2 C12 C13 C14 179.1(2) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C13 C14 C15 C16 1.7(4) . . . . ?
C13 C14 C15 N3 -177.0(2) . . . . ?
C20 N3 C15 C14 -141.5(3) . . . . ?
C18 N3 C15 C14 44.6(4) . . . . ?
C20 N3 C15 C16 39.8(3) . . . . ?
C18 N3 C15 C16 -134.1(3) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
N3 C15 C16 C17 178.4(2) . . . . ?
C13 C12 C17 C16 1.1(4) . . . . ?
N2 C12 C17 C16 -177.7(2) . . . . ?
C15 C16 C17 C12 -1.1(4) . . . . ?
C20 N3 C18 C19 0.5(3) . . . . ?
C15 N3 C18 C19 175.5(2) . . . . ?
N3 C18 C19 N4 0.0(4) . . . . ?
C20 N4 C19 C18 -0.5(3) . . . . ?
Mn1 N4 C19 C18 -164.6(2) 1_645 . . . ?
C19 N4 C20 N3 0.9(3) . . . . ?
Mn1 N4 C20 N3 165.87(14) 1_645 . . . ?
C18 N3 C20 N4 -0.9(3) . . . . ?
C15 N3 C20 N4 -175.8(2) . . . . ?

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.052



