# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_e_c01
_database_code_depnum_ccdc_archive 'CCDC 1031995'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cl2 Mn N6'
_chemical_formula_sum            'C16 H14 Cl2 Mn N6'
_chemical_formula_weight         416.17

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   10.562(2)
_cell_length_b                   14.818(3)
_cell_length_c                   13.274(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.500(4)
_cell_angle_gamma                90.00
_cell_volume                     2076.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2626
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.37

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    0.903
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.442650
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 Bruker 2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12727
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         28.34
_reflns_number_total             2567
_reflns_number_gt                1908
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          SQUEEZE

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2567
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.494 0.250 96 27 ' '
2 0.000 0.506 0.750 94 27 ' '
3 0.500 0.994 0.250 96 27 ' '
4 0.500 0.006 0.750 94 27 ' '
_platon_squeeze_details          
;
Spurious electron density peaks non attribuitable to any solvent molecule 
 were removed using the SQUEEZE option in PLATON.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.0000 0.11617(3) 0.7500 0.03334(18) Uani 1 2 d S . .
Cl1 Cl 0.09362(7) 0.00646(5) 0.87141(5) 0.0515(2) Uani 1 1 d . . .
N1 N 0.12727(19) 0.23198(14) 0.81892(15) 0.0393(5) Uani 1 1 d . . .
C1 C 0.1053(3) 0.2765(2) 0.9046(2) 0.0507(7) Uani 1 1 d . . .
H1A H 0.0330 0.2622 0.9398 0.061 Uiso 1 1 calc R . .
N2 N 0.1978(2) 0.10868(16) 0.55939(15) 0.0478(6) Uani 1 1 d . . .
H2B H 0.1560 0.0692 0.5246 0.057 Uiso 1 1 calc R . .
C2 C 0.1848(3) 0.3425(2) 0.9429(2) 0.0630(9) Uani 1 1 d . . .
H2A H 0.1665 0.3719 1.0026 0.076 Uiso 1 1 calc R . .
N3 N 0.1568(2) 0.14605(15) 0.64515(14) 0.0387(5) Uani 1 1 d . . .
C3 C 0.2917(3) 0.3640(2) 0.8914(3) 0.0606(8) Uani 1 1 d . . .
H3A H 0.3477 0.4075 0.9164 0.073 Uiso 1 1 calc R . .
C4 C 0.3150(3) 0.3201(2) 0.8017(2) 0.0517(7) Uani 1 1 d . . .
H4A H 0.3853 0.3349 0.7644 0.062 Uiso 1 1 calc R . .
C5 C 0.2313(2) 0.25359(17) 0.76860(18) 0.0390(6) Uani 1 1 d . . .
C6 C 0.2490(2) 0.20268(18) 0.67510(18) 0.0407(6) Uani 1 1 d . . .
C7 C 0.3478(3) 0.2010(2) 0.6076(2) 0.0678(10) Uani 1 1 d . . .
H7A H 0.4227 0.2339 0.6112 0.081 Uiso 1 1 calc R . .
C8 C 0.3106(3) 0.1403(2) 0.5351(2) 0.0689(10) Uani 1 1 d . . .
H8A H 0.3562 0.1242 0.4788 0.083 Uiso 1 1 calc R . .


_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 N3 2.236(2) . ?
Mn1 N3 2.236(2) 2_556 ?
Mn1 N1 2.351(2) . ?
Mn1 N1 2.351(2) 2_556 ?
Mn1 Cl1 2.4768(8) 2_556 ?
Mn1 Cl1 2.4768(8) . ?
N1 C5 1.339(3) . ?
N1 C1 1.340(3) . ?
C1 C2 1.377(4) . ?
C1 H1A 0.9300 . ?
N2 C8 1.329(4) . ?
N2 N3 1.347(3) . ?
N2 H2B 0.8600 . ?
C2 C3 1.372(5) . ?
C2 H2A 0.9300 . ?
N3 C6 1.337(3) . ?
C3 C4 1.384(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.468(3) . ?
C6 C7 1.393(4) . ?
C7 C8 1.367(5) . ?
C7 H7A 0.9300 . ?
C8 H8A 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
N3 Mn1 N3 157.15(12) . 2_556 ?
N3 Mn1 N1 70.87(7) . . ?
N3 Mn1 N1 92.21(8) 2_556 . ?
N3 Mn1 N1 92.21(8) . 2_556 ?
N3 Mn1 N1 70.87(7) 2_556 2_556 ?
N1 Mn1 N1 86.20(10) . 2_556 ?
N3 Mn1 Cl1 90.84(6) . 2_556 ?
N3 Mn1 Cl1 104.21(6) 2_556 2_556 ?
N1 Mn1 Cl1 161.27(5) . 2_556 ?
N1 Mn1 Cl1 90.66(6) 2_556 2_556 ?
N3 Mn1 Cl1 104.21(6) . . ?
N3 Mn1 Cl1 90.84(6) 2_556 . ?
N1 Mn1 Cl1 90.66(5) . . ?
N1 Mn1 Cl1 161.27(5) 2_556 . ?
Cl1 Mn1 Cl1 97.95(4) 2_556 . ?
C5 N1 C1 117.9(2) . . ?
C5 N1 Mn1 116.65(16) . . ?
C1 N1 Mn1 125.45(18) . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1A 118.5 . . ?
C2 C1 H1A 118.5 . . ?
C8 N2 N3 111.7(2) . . ?
C8 N2 H2B 124.1 . . ?
N3 N2 H2B 124.1 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C6 N3 N2 105.2(2) . . ?
C6 N3 Mn1 118.96(15) . . ?
N2 N3 Mn1 134.75(17) . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
N1 C5 C4 122.4(2) . . ?
N1 C5 C6 115.0(2) . . ?
C4 C5 C6 122.6(2) . . ?
N3 C6 C7 110.4(2) . . ?
N3 C6 C5 117.8(2) . . ?
C7 C6 C5 131.8(3) . . ?
C8 C7 C6 105.0(3) . . ?
C8 C7 H7A 127.5 . . ?
C6 C7 H7A 127.5 . . ?
N2 C8 C7 107.7(3) . . ?
N2 C8 H8A 126.2 . . ?
C7 C8 H8A 126.2 . . ?

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
N3 Mn1 N1 C5 -4.67(16) . . . . ?
N3 Mn1 N1 C5 -168.99(17) 2_556 . . . ?
N1 Mn1 N1 C5 -98.33(18) 2_556 . . . ?
Cl1 Mn1 N1 C5 -17.5(3) 2_556 . . . ?
Cl1 Mn1 N1 C5 100.15(17) . . . . ?
N3 Mn1 N1 C1 176.5(2) . . . . ?
N3 Mn1 N1 C1 12.2(2) 2_556 . . . ?
N1 Mn1 N1 C1 82.9(2) 2_556 . . . ?
Cl1 Mn1 N1 C1 163.68(17) 2_556 . . . ?
Cl1 Mn1 N1 C1 -78.6(2) . . . . ?
C5 N1 C1 C2 -0.4(4) . . . . ?
Mn1 N1 C1 C2 178.4(2) . . . . ?
N1 C1 C2 C3 0.0(5) . . . . ?
C8 N2 N3 C6 -0.4(3) . . . . ?
C8 N2 N3 Mn1 -167.8(2) . . . . ?
N3 Mn1 N3 C6 51.70(18) 2_556 . . . ?
N1 Mn1 N3 C6 7.61(18) . . . . ?
N1 Mn1 N3 C6 92.82(19) 2_556 . . . ?
Cl1 Mn1 N3 C6 -176.49(19) 2_556 . . . ?
Cl1 Mn1 N3 C6 -78.07(19) . . . . ?
N3 Mn1 N3 N2 -142.3(2) 2_556 . . . ?
N1 Mn1 N3 N2 173.7(3) . . . . ?
N1 Mn1 N3 N2 -101.1(2) 2_556 . . . ?
Cl1 Mn1 N3 N2 -10.4(2) 2_556 . . . ?
Cl1 Mn1 N3 N2 88.0(2) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C2 C3 C4 C5 -2.1(5) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
Mn1 N1 C5 C4 -179.4(2) . . . . ?
C1 N1 C5 C6 -179.6(2) . . . . ?
Mn1 N1 C5 C6 1.6(3) . . . . ?
C3 C4 C5 N1 1.7(4) . . . . ?
C3 C4 C5 C6 -179.3(3) . . . . ?
N2 N3 C6 C7 0.2(3) . . . . ?
Mn1 N3 C6 C7 170.0(2) . . . . ?
N2 N3 C6 C5 -179.6(2) . . . . ?
Mn1 N3 C6 C5 -9.8(3) . . . . ?
N1 C5 C6 N3 5.2(3) . . . . ?
C4 C5 C6 N3 -173.9(2) . . . . ?
N1 C5 C6 C7 -174.5(3) . . . . ?
C4 C5 C6 C7 6.4(5) . . . . ?
N3 C6 C7 C8 0.1(4) . . . . ?
C5 C6 C7 C8 179.8(3) . . . . ?
N3 N2 C8 C7 0.4(4) . . . . ?
C6 C7 C8 N2 -0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_e_c02
_database_code_depnum_ccdc_archive 'CCDC 1031996'
_audit_update_record             
;
2015-09-02 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 F6 Mn N6 O6 S2'
_chemical_formula_sum            'C18 H14 F6 Mn N6 O6 S2'
_chemical_formula_weight         643.41

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'
S S 0.1246 0.1234 '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                   9.879(2)
_cell_length_b                   10.616(3)
_cell_length_c                   13.434(3)
_cell_angle_alpha                86.091(5)
_cell_angle_beta                 83.134(5)
_cell_angle_gamma                62.840(4)
_cell_volume                     1244.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1721
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      20.52

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             646
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.791
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.589463
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15958
_diffrn_reflns_av_unetI/netI     0.1126
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.329
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5985
_reflns_number_gt                3488
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Constrains/restrains used in the refinement:
 The C-F bond lenghts were restrained to 1.39A
 The ADPs for the disordered F were constrained with
 the EADP instruction taking the Uij of the F4 F5 and F6
 atoms as reference. The EADP constrain also was used for atom
 C17 taking as reference C18.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0740P)²+2.5547P] 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         5985
_refine_ls_number_parameters     338
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1574
_refine_ls_R_factor_gt           0.0935
_refine_ls_wR_factor_ref         0.2334
_refine_ls_wR_factor_gt          0.1950
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.064
_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
Mn1 Mn 0.22644(10) 0.17990(10) 0.23496(7) 0.0348(3) Uani 1 1 d . . . . .
S1 S 0.17048(19) 0.49082(18) 0.10048(13) 0.0424(4) Uani 1 1 d . . . . .
N1 N 0.2511(6) 0.0639(6) 0.0916(4) 0.0414(12) Uani 1 1 d . . . . .
O1 O 0.2440(6) 0.3491(5) 0.1429(4) 0.0585(14) Uani 1 1 d . . . . .
C1 C 0.1455(9) 0.0995(9) 0.0272(5) 0.0568(19) Uani 1 1 d . . . . .
H1A H 0.0566 0.1844 0.0363 0.068 Uiso 1 1 calc R U . . .
F4 F 0.3921(7) 0.3728(6) 0.5769(4) 0.1063(17) Uani 1 1 d D . . . .
F5 F 0.3849(8) 0.4549(6) 0.4275(5) 0.1133(18) Uani 1 1 d D . . . .
F6 F 0.1803(7) 0.4874(6) 0.5140(5) 0.1144(18) Uani 1 1 d D . . . .
F1 F 0.3735(11) 0.5435(19) 0.1170(12) 0.1063(17) Uani 0.348(7) 1 d D . P A 1
F2 F 0.213(3) 0.7082(13) 0.1172(15) 0.1133(18) Uani 0.348(7) 1 d D . P A 1
F3 F 0.298(2) 0.5513(17) 0.2559(10) 0.1144(18) Uani 0.348(7) 1 d D . P A 1
F1' F 0.3828(9) 0.5328(10) 0.1792(10) 0.1133(18) Uani 0.652(7) 1 d D . P A 2
F2' F 0.1694(13) 0.7289(6) 0.1494(9) 0.1144(18) Uani 0.652(7) 1 d D . P A 2
F3' F 0.1657(12) 0.5953(10) 0.2664(5) 0.1063(17) Uani 0.652(7) 1 d D . P A 2
N3 N 0.4629(5) 0.0015(5) 0.2196(4) 0.0382(12) Uani 1 1 d . . . . .
S2 S 0.34141(19) 0.22909(17) 0.45124(13) 0.0412(4) Uani 1 1 d . . . . .
O2 O 0.0103(6) 0.5622(6) 0.1245(5) 0.088(2) Uani 1 1 d . . . . .
C2 C 0.1632(10) 0.0153(11) -0.0527(6) 0.070(2) Uani 1 1 d . . . . .
H2A H 0.0873 0.0427 -0.0959 0.084 Uiso 1 1 calc R U . . .
N2 N 0.5845(6) -0.0573(6) 0.2732(4) 0.0464(14) Uani 1 1 d . . . . .
H2B H 0.5930 -0.0198 0.3254 0.056 Uiso 1 1 calc R U . . .
O3 O 0.2253(8) 0.5025(7) 0.0000(4) 0.093(2) Uani 1 1 d . . . . .
C3 C 0.2950(11) -0.1095(10) -0.0667(6) 0.071(2) Uani 1 1 d . . . . .
H3A H 0.3089 -0.1686 -0.1190 0.085 Uiso 1 1 calc R U . . .
N4 N 0.1507(6) 0.0278(6) 0.3290(4) 0.0425(13) Uani 1 1 d . . . . .
O4 O 0.2549(6) 0.2706(5) 0.3647(4) 0.0652(15) Uani 1 1 d . . . . .
C4 C 0.4060(9) -0.1462(8) -0.0029(6) 0.0573(19) Uani 1 1 d . . . . .
H4A H 0.4969 -0.2292 -0.0125 0.069 Uiso 1 1 calc R U . . .
N6 N -0.0259(6) 0.2768(6) 0.2451(4) 0.0417(13) Uani 1 1 d . . . . .
C5 C 0.3813(7) -0.0584(7) 0.0759(5) 0.0394(14) Uani 1 1 d . . . . .
O5 O 0.5034(6) 0.1506(5) 0.4271(4) 0.0667(15) Uani 1 1 d . . . . .
O6 O 0.2772(7) 0.1763(6) 0.5329(4) 0.0731(16) Uani 1 1 d . . . . .
N5 N -0.1392(6) 0.3974(6) 0.2135(4) 0.0496(15) Uani 1 1 d . . . . .
H5A H -0.1248 0.4632 0.1803 0.059 Uiso 1 1 calc R U . . .
C6 C 0.4953(7) -0.0911(7) 0.1468(5) 0.0405(15) Uani 1 1 d . . . . .
C7 C 0.6391(8) -0.2064(7) 0.1536(5) 0.0516(18) Uani 1 1 d . . . . .
H7A H 0.6888 -0.2835 0.1112 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6900(8) -0.1809(8) 0.2357(5) 0.057(2) Uani 1 1 d . . . . .
H8A H 0.7824 -0.2393 0.2614 0.069 Uiso 1 1 calc R U . . .
C9 C 0.2448(8) -0.0959(7) 0.3697(5) 0.0479(17) Uani 1 1 d . . . . .
H9A H 0.3484 -0.1205 0.3666 0.057 Uiso 1 1 calc R U . . .
C10 C 0.1921(9) -0.1887(7) 0.4164(6) 0.0564(19) Uani 1 1 d . . . . .
H10A H 0.2594 -0.2738 0.4444 0.068 Uiso 1 1 calc R U . . .
C11 C 0.0404(9) -0.1529(8) 0.4202(6) 0.060(2) Uani 1 1 d . . . . .
H11A H 0.0035 -0.2143 0.4501 0.072 Uiso 1 1 calc R U . . .
C12 C -0.0595(9) -0.0239(8) 0.3792(5) 0.0514(18) Uani 1 1 d . . . . .
H12A H -0.1633 0.0021 0.3813 0.062 Uiso 1 1 calc R U . . .
C13 C 0.0002(7) 0.0651(7) 0.3350(5) 0.0387(14) Uani 1 1 d . . . . .
C14 C -0.0956(7) 0.2040(7) 0.2921(5) 0.0393(14) Uani 1 1 d . . . . .
C15 C -0.2544(8) 0.2807(8) 0.2909(5) 0.0520(18) Uani 1 1 d . . . . .
H15A H -0.3285 0.2543 0.3189 0.062 Uiso 1 1 calc R U . . .
C16 C -0.2762(7) 0.4036(8) 0.2394(6) 0.0559(19) Uani 1 1 d . . . . .
H16A H -0.3697 0.4775 0.2251 0.067 Uiso 1 1 calc R U . . .
C17 C 0.2287(8) 0.5839(6) 0.1673(5) 0.082(2) Uani 1 1 d D . . . .
C18 C 0.3219(11) 0.3911(10) 0.4940(7) 0.082(2) Uani 1 1 d D . . . .


_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 2.154(5) . ?
Mn1 O1 2.172(5) . ?
Mn1 N6 2.211(5) . ?
Mn1 N3 2.233(5) . ?
Mn1 N1 2.286(5) . ?
Mn1 N4 2.316(5) . ?
S1 O3 1.412(6) . ?
S1 O2 1.414(5) . ?
S1 O1 1.449(5) . ?
S1 C17 1.696(8) . ?
N1 C1 1.338(8) . ?
N1 C5 1.354(8) . ?
C1 C2 1.388(11) . ?
C1 H1A 0.9300 . ?
F4 C18 1.339(9) . ?
F5 C18 1.347(10) . ?
F6 C18 1.310(9) . ?
F1 C17 1.3906(11) . ?
F1 F2 1.74(2) . ?
F2 C17 1.3896(11) . ?
F3 C17 1.3895(11) . ?
F1' C17 1.3892(11) . ?
F2' C17 1.3894(11) . ?
F3' C17 1.3902(11) . ?
N3 C6 1.340(8) . ?
N3 N2 1.346(7) . ?
S2 O6 1.413(5) . ?
S2 O5 1.434(5) . ?
S2 O4 1.449(5) . ?
S2 C18 1.770(10) . ?
C2 C3 1.373(12) . ?
C2 H2A 0.9300 . ?
N2 C8 1.333(8) . ?
N2 H2B 0.8600 . ?
C3 C4 1.370(11) . ?
C3 H3A 0.9300 . ?
N4 C9 1.340(8) . ?
N4 C13 1.346(8) . ?
C4 C5 1.383(9) . ?
C4 H4A 0.9300 . ?
N6 C14 1.336(8) . ?
N6 N5 1.343(7) . ?
C5 C6 1.466(9) . ?
N5 C16 1.329(8) . ?
N5 H5A 0.8600 . ?
C6 C7 1.398(8) . ?
C7 C8 1.357(10) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C10 1.393(9) . ?
C9 H9A 0.9300 . ?
C10 C11 1.363(10) . ?
C10 H10A 0.9300 . ?
C11 C12 1.395(10) . ?
C11 H11A 0.9300 . ?
C12 C13 1.393(9) . ?
C12 H12A 0.9300 . ?
C13 C14 1.464(9) . ?
C14 C15 1.400(9) . ?
C15 C16 1.372(10) . ?
C15 H15A 0.9300 . ?
C16 H16A 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 O1 89.3(2) . . ?
O4 Mn1 N6 99.9(2) . . ?
O1 Mn1 N6 94.94(19) . . ?
O4 Mn1 N3 96.00(19) . . ?
O1 Mn1 N3 104.22(19) . . ?
N6 Mn1 N3 155.2(2) . . ?
O4 Mn1 N1 167.9(2) . . ?
O1 Mn1 N1 88.79(19) . . ?
N6 Mn1 N1 92.2(2) . . ?
N3 Mn1 N1 72.94(18) . . ?
O4 Mn1 N4 93.7(2) . . ?
O1 Mn1 N4 167.31(18) . . ?
N6 Mn1 N4 72.41(19) . . ?
N3 Mn1 N4 87.75(19) . . ?
N1 Mn1 N4 90.8(2) . . ?
O3 S1 O2 116.5(4) . . ?
O3 S1 O1 114.0(4) . . ?
O2 S1 O1 114.5(3) . . ?
O3 S1 C17 105.0(4) . . ?
O2 S1 C17 101.2(4) . . ?
O1 S1 C17 103.2(3) . . ?
C1 N1 C5 117.8(6) . . ?
C1 N1 Mn1 126.4(5) . . ?
C5 N1 Mn1 115.6(4) . . ?
S1 O1 Mn1 149.2(3) . . ?
N1 C1 C2 122.8(7) . . ?
N1 C1 H1A 118.6 . . ?
C2 C1 H1A 118.6 . . ?
C17 F1 F2 51.1(6) . . ?
C17 F2 F1 51.2(6) . . ?
C6 N3 N2 104.7(5) . . ?
C6 N3 Mn1 116.7(4) . . ?
N2 N3 Mn1 137.7(4) . . ?
O6 S2 O5 116.0(3) . . ?
O6 S2 O4 114.1(3) . . ?
O5 S2 O4 114.0(3) . . ?
O6 S2 C18 104.4(4) . . ?
O5 S2 C18 102.6(4) . . ?
O4 S2 C18 103.7(4) . . ?
C3 C2 C1 118.6(7) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C8 N2 N3 111.8(6) . . ?
C8 N2 H2B 124.1 . . ?
N3 N2 H2B 124.1 . . ?
C4 C3 C2 119.5(8) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C9 N4 C13 119.2(6) . . ?
C9 N4 Mn1 125.4(4) . . ?
C13 N4 Mn1 115.3(4) . . ?
S2 O4 Mn1 140.3(3) . . ?
C3 C4 C5 119.2(7) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C14 N6 N5 105.0(5) . . ?
C14 N6 Mn1 118.3(4) . . ?
N5 N6 Mn1 136.6(4) . . ?
N1 C5 C4 122.1(6) . . ?
N1 C5 C6 115.8(6) . . ?
C4 C5 C6 122.1(6) . . ?
C16 N5 N6 112.3(6) . . ?
C16 N5 H5A 123.9 . . ?
N6 N5 H5A 123.9 . . ?
N3 C6 C7 110.8(6) . . ?
N3 C6 C5 118.0(5) . . ?
C7 C6 C5 131.2(6) . . ?
C8 C7 C6 104.7(6) . . ?
C8 C7 H7A 127.7 . . ?
C6 C7 H7A 127.7 . . ?
N2 C8 C7 108.0(6) . . ?
N2 C8 H8A 126.0 . . ?
C7 C8 H8A 126.0 . . ?
N4 C9 C10 122.0(7) . . ?
N4 C9 H9A 119.0 . . ?
C10 C9 H9A 119.0 . . ?
C11 C10 C9 118.9(7) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C10 C11 C12 119.8(7) . . ?
C10 C11 H11A 120.1 . . ?
C12 C11 H11A 120.1 . . ?
C13 C12 C11 118.3(7) . . ?
C13 C12 H12A 120.8 . . ?
C11 C12 H12A 120.8 . . ?
N4 C13 C12 121.7(6) . . ?
N4 C13 C14 115.8(6) . . ?
C12 C13 C14 122.5(6) . . ?
N6 C14 C15 110.6(6) . . ?
N6 C14 C13 117.8(5) . . ?
C15 C14 C13 131.7(6) . . ?
C16 C15 C14 104.7(6) . . ?
C16 C15 H15A 127.6 . . ?
C14 C15 H15A 127.6 . . ?
N5 C16 C15 107.4(6) . . ?
N5 C16 H16A 126.3 . . ?
C15 C16 H16A 126.3 . . ?
F1' C17 F2' 107.5(8) . . ?
F3 C17 F2 117.2(14) . . ?
F1' C17 F3' 101.3(8) . . ?
F2' C17 F3' 95.3(8) . . ?
F3 C17 F1 87.2(11) . . ?
F2 C17 F1 77.7(13) . . ?
F1' C17 S1 120.1(6) . . ?
F2' C17 S1 118.0(7) . . ?
F3 C17 S1 131.3(9) . . ?
F2 C17 S1 111.3(11) . . ?
F3' C17 S1 110.6(5) . . ?
F1 C17 S1 98.8(8) . . ?
F6 C18 F4 106.9(8) . . ?
F6 C18 F5 104.5(8) . . ?
F4 C18 F5 104.9(8) . . ?
F6 C18 S2 114.6(7) . . ?
F4 C18 S2 111.8(6) . . ?
F5 C18 S2 113.4(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
O3 S1 O1 Mn1 -139.2(7) . . . . ?
O2 S1 O1 Mn1 -1.5(8) . . . . ?
C17 S1 O1 Mn1 107.6(7) . . . . ?
C5 N1 C1 C2 1.4(11) . . . . ?
Mn1 N1 C1 C2 -173.1(6) . . . . ?
N1 C1 C2 C3 -0.5(13) . . . . ?
C6 N3 N2 C8 0.7(8) . . . . ?
Mn1 N3 N2 C8 168.5(5) . . . . ?
C1 C2 C3 C4 -1.1(13) . . . . ?
O6 S2 O4 Mn1 -83.5(6) . . . . ?
O5 S2 O4 Mn1 52.9(7) . . . . ?
C18 S2 O4 Mn1 163.6(6) . . . . ?
C2 C3 C4 C5 1.6(12) . . . . ?
C1 N1 C5 C4 -0.8(9) . . . . ?
Mn1 N1 C5 C4 174.3(5) . . . . ?
C1 N1 C5 C6 178.4(6) . . . . ?
Mn1 N1 C5 C6 -6.5(7) . . . . ?
C3 C4 C5 N1 -0.7(11) . . . . ?
C3 C4 C5 C6 -179.9(7) . . . . ?
C14 N6 N5 C16 0.6(8) . . . . ?
Mn1 N6 N5 C16 179.2(5) . . . . ?
N2 N3 C6 C7 -1.5(7) . . . . ?
Mn1 N3 C6 C7 -172.3(4) . . . . ?
N2 N3 C6 C5 178.5(5) . . . . ?
Mn1 N3 C6 C5 7.7(7) . . . . ?
N1 C5 C6 N3 -0.6(8) . . . . ?
C4 C5 C6 N3 178.6(6) . . . . ?
N1 C5 C6 C7 179.4(7) . . . . ?
C4 C5 C6 C7 -1.4(11) . . . . ?
N3 C6 C7 C8 1.7(8) . . . . ?
C5 C6 C7 C8 -178.3(7) . . . . ?
N3 N2 C8 C7 0.4(9) . . . . ?
C6 C7 C8 N2 -1.2(8) . . . . ?
C13 N4 C9 C10 1.3(10) . . . . ?
Mn1 N4 C9 C10 -173.1(5) . . . . ?
N4 C9 C10 C11 0.4(11) . . . . ?
C9 C10 C11 C12 -1.1(12) . . . . ?
C10 C11 C12 C13 0.1(11) . . . . ?
C9 N4 C13 C12 -2.3(10) . . . . ?
Mn1 N4 C13 C12 172.6(5) . . . . ?
C9 N4 C13 C14 177.8(6) . . . . ?
Mn1 N4 C13 C14 -7.3(7) . . . . ?
C11 C12 C13 N4 1.7(10) . . . . ?
C11 C12 C13 C14 -178.5(6) . . . . ?
N5 N6 C14 C15 -0.8(7) . . . . ?
Mn1 N6 C14 C15 -179.7(4) . . . . ?
N5 N6 C14 C13 179.7(5) . . . . ?
Mn1 N6 C14 C13 0.8(8) . . . . ?
N4 C13 C14 N6 4.5(9) . . . . ?
C12 C13 C14 N6 -175.3(6) . . . . ?
N4 C13 C14 C15 -174.9(7) . . . . ?
C12 C13 C14 C15 5.3(11) . . . . ?
N6 C14 C15 C16 0.7(8) . . . . ?
C13 C14 C15 C16 -179.9(7) . . . . ?
N6 N5 C16 C15 -0.1(9) . . . . ?
C14 C15 C16 N5 -0.3(8) . . . . ?
F1 F2 C17 F1' 30.7(8) . . . . ?
F1 F2 C17 F2' 153(4) . . . . ?
F1 F2 C17 F3 80.3(12) . . . . ?
F1 F2 C17 F3' 136.5(11) . . . . ?
F1 F2 C17 S1 -94.8(10) . . . . ?
F2 F1 C17 F1' -118.9(18) . . . . ?
F2 F1 C17 F2' -10.1(14) . . . . ?
F2 F1 C17 F3 -118.6(13) . . . . ?
F2 F1 C17 F3' -116.8(17) . . . . ?
F2 F1 C17 S1 110.1(11) . . . . ?
O3 S1 C17 F1' -69.9(8) . . . . ?
O2 S1 C17 F1' 168.4(7) . . . . ?
O1 S1 C17 F1' 49.7(8) . . . . ?
O3 S1 C17 F2' 64.6(8) . . . . ?
O2 S1 C17 F2' -57.0(8) . . . . ?
O1 S1 C17 F2' -175.8(7) . . . . ?
O3 S1 C17 F3 -133.6(13) . . . . ?
O2 S1 C17 F3 104.7(13) . . . . ?
O1 S1 C17 F3 -14.0(13) . . . . ?
O3 S1 C17 F2 40.6(12) . . . . ?
O2 S1 C17 F2 -81.0(11) . . . . ?
O1 S1 C17 F2 160.2(11) . . . . ?
O3 S1 C17 F3' 172.7(6) . . . . ?
O2 S1 C17 F3' 51.1(6) . . . . ?
O1 S1 C17 F3' -67.7(6) . . . . ?
O3 S1 C17 F1 -39.6(9) . . . . ?
O2 S1 C17 F1 -161.2(9) . . . . ?
O1 S1 C17 F1 80.0(9) . . . . ?
O6 S2 C18 F6 -63.6(8) . . . . ?
O5 S2 C18 F6 175.0(7) . . . . ?
O4 S2 C18 F6 56.2(8) . . . . ?
O6 S2 C18 F4 58.3(8) . . . . ?
O5 S2 C18 F4 -63.1(8) . . . . ?
O4 S2 C18 F4 178.0(7) . . . . ?
O6 S2 C18 F5 176.6(6) . . . . ?
O5 S2 C18 F5 55.2(7) . . . . ?
O4 S2 C18 F5 -63.6(7) . . . . ?

_refine_diff_density_max         0.768
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_e_c03
_database_code_depnum_ccdc_archive 'CCDC 1031997'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 Mn N6 O8'
_chemical_formula_sum            'C24 H28 Mn N6 O8'
_chemical_formula_weight         583.46

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   13.439(3)
_cell_length_b                   10.422(3)
_cell_length_c                   20.069(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2811.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3506
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      22.96

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1212
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.401869
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40443
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.30
_reflns_number_total             3467
_reflns_number_gt                2102
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
 The N-h and O-H hydrogens were located in the difference Fourier map and
 refined freely.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0504P)²+0.3540P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3467
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.5000 0.10731(4) 0.7500 0.03898(16) Uani 1 2 d S . .
O1 O 0.54258(13) 0.24564(16) 0.82246(10) 0.0623(5) Uani 1 1 d . . .
N1 N 0.43546(13) -0.06149(17) 0.68660(10) 0.0435(5) Uani 1 1 d . . .
H1 H 0.701(2) 0.181(3) 0.6502(15) 0.075(10) Uiso 1 1 d . . .
C1 C 0.48636(17) -0.1301(2) 0.64153(14) 0.0525(6) Uani 1 1 d . . .
H1A H 0.5511 -0.1057 0.6313 0.063 Uiso 1 1 calc R . .
N2 N 0.72306(16) 0.1247(2) 0.67509(12) 0.0531(6) Uani 1 1 d . . .
O2 O 0.42195(13) 0.26067(18) 0.89644(10) 0.0715(6) Uani 1 1 d . . .
C2 C 0.4466(2) -0.2352(2) 0.60992(14) 0.0627(8) Uani 1 1 d . . .
H2A H 0.4833 -0.2798 0.5782 0.075 Uiso 1 1 calc R . .
N3 N 0.65827(13) 0.06887(17) 0.71732(10) 0.0437(5) Uani 1 1 d . . .
C3 C 0.3523(2) -0.2731(3) 0.62566(15) 0.0657(8) Uani 1 1 d . . .
H3A H 0.3248 -0.3447 0.6051 0.079 Uiso 1 1 calc R . .
C4 C 0.29858(19) -0.2062(2) 0.67147(13) 0.0539(6) Uani 1 1 d . . .
H4A H 0.2344 -0.2316 0.6826 0.065 Uiso 1 1 calc R . .
C5 C 0.34130(16) -0.0995(2) 0.70120(12) 0.0409(5) Uani 1 1 d . . .
C6 C 0.71046(15) -0.0217(2) 0.74924(12) 0.0400(5) Uani 1 1 d . . .
C7 C 0.80972(17) -0.0226(3) 0.72633(15) 0.0594(7) Uani 1 1 d . . .
H7A H 0.8612 -0.0762 0.7400 0.071 Uiso 1 1 calc R . .
C8 C 0.81353(19) 0.0728(3) 0.67941(15) 0.0610(7) Uani 1 1 d . . .
H8A H 0.8692 0.0970 0.6550 0.073 Uiso 1 1 calc R . .
C9 C 0.50510(18) 0.2898(2) 0.87467(13) 0.0487(6) Uani 1 1 d . . .
C10 C 0.5656(2) 0.3844(3) 0.9144(2) 0.0946(12) Uani 1 1 d . . .
H10A H 0.5974 0.4438 0.8847 0.142 Uiso 1 1 calc R . .
H10B H 0.6153 0.3392 0.9396 0.142 Uiso 1 1 calc R . .
H10C H 0.5227 0.4303 0.9443 0.142 Uiso 1 1 calc R . .
O1W O 0.32278(16) 0.4087(2) 0.97469(11) 0.0757(6) Uani 1 1 d . . .
H1W H 0.363(3) 0.343(3) 0.9472(18) 0.125(13) Uiso 1 1 d . . .
C1W C 0.2283(2) 0.3870(3) 0.96705(15) 0.0664(8) Uani 1 1 d . . .
O2W O 0.19629(15) 0.3029(2) 0.93186(13) 0.0932(8) Uani 1 1 d . . .
C2W C 0.1619(3) 0.4774(4) 1.00541(19) 0.1001(12) Uani 1 1 d . . .
H2WA H 0.1043 0.4318 1.0209 0.150 Uiso 1 1 calc R . .
H2WB H 0.1414 0.5465 0.9769 0.150 Uiso 1 1 calc R . .
H2WC H 0.1977 0.5115 1.0428 0.150 Uiso 1 1 calc R . .


_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 2.1262(18) . ?
Mn1 O1 2.1262(18) 3_656 ?
Mn1 N3 2.2616(18) 3_656 ?
Mn1 N3 2.2616(18) . ?
Mn1 N1 2.3381(19) . ?
Mn1 N1 2.3381(19) 3_656 ?
O1 C9 1.250(3) . ?
N1 C1 1.341(3) . ?
N1 C5 1.358(3) . ?
C1 C2 1.374(3) . ?
C1 H1A 0.9300 . ?
N2 C8 1.333(3) . ?
N2 N3 1.347(3) . ?
N2 H1 0.83(3) . ?
O2 C9 1.238(3) . ?
C2 C3 1.364(4) . ?
C2 H2A 0.9300 . ?
N3 C6 1.339(3) . ?
C3 C4 1.361(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.460(3) 3_656 ?
C6 C7 1.411(3) . ?
C6 C5 1.460(3) 3_656 ?
C7 C8 1.371(4) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C10 1.507(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O1W C1W 1.298(3) . ?
O1W H1W 1.04(4) . ?
C1W O2W 1.206(3) . ?
C1W C2W 1.509(4) . ?
C2W H2WA 0.9600 . ?
C2W H2WB 0.9600 . ?
C2W H2WC 0.9600 . ?

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 O1 94.61(11) . 3_656 ?
O1 Mn1 N3 100.07(7) . 3_656 ?
O1 Mn1 N3 93.75(7) 3_656 3_656 ?
O1 Mn1 N3 93.75(7) . . ?
O1 Mn1 N3 100.07(7) 3_656 . ?
N3 Mn1 N3 159.59(9) 3_656 . ?
O1 Mn1 N1 169.20(7) . . ?
O1 Mn1 N1 92.19(7) 3_656 . ?
N3 Mn1 N1 71.08(7) 3_656 . ?
N3 Mn1 N1 93.31(7) . . ?
O1 Mn1 N1 92.19(7) . 3_656 ?
O1 Mn1 N1 169.20(7) 3_656 3_656 ?
N3 Mn1 N1 93.31(7) 3_656 3_656 ?
N3 Mn1 N1 71.08(7) . 3_656 ?
N1 Mn1 N1 82.39(9) . 3_656 ?
C9 O1 Mn1 135.59(16) . . ?
C1 N1 C5 117.7(2) . . ?
C1 N1 Mn1 125.41(15) . . ?
C5 N1 Mn1 116.59(15) . . ?
N1 C1 C2 122.6(2) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C8 N2 N3 111.9(2) . . ?
C8 N2 H1 131(2) . . ?
N3 N2 H1 117(2) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C6 N3 N2 105.46(18) . . ?
C6 N3 Mn1 118.60(15) . . ?
N2 N3 Mn1 135.56(15) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
N1 C5 C4 121.8(2) . . ?
N1 C5 C6 115.41(19) . 3_656 ?
C4 C5 C6 122.8(2) . 3_656 ?
N3 C6 C7 110.1(2) . . ?
N3 C6 C5 117.90(18) . 3_656 ?
C7 C6 C5 132.0(2) . 3_656 ?
C8 C7 C6 104.7(2) . . ?
C8 C7 H7A 127.6 . . ?
C6 C7 H7A 127.6 . . ?
N2 C8 C7 107.7(2) . . ?
N2 C8 H8A 126.1 . . ?
C7 C8 H8A 126.1 . . ?
O2 C9 O1 124.7(2) . . ?
O2 C9 C10 117.4(2) . . ?
O1 C9 C10 117.9(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1W O1W H1W 109(2) . . ?
O2W C1W O1W 123.0(3) . . ?
O2W C1W C2W 122.8(3) . . ?
O1W C1W C2W 114.2(3) . . ?
C1W C2W H2WA 109.5 . . ?
C1W C2W H2WB 109.5 . . ?
H2WA C2W H2WB 109.5 . . ?
C1W C2W H2WC 109.5 . . ?
H2WA C2W H2WC 109.5 . . ?
H2WB C2W H2WC 109.5 . . ?

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
O1 Mn1 O1 C9 103.1(3) 3_656 . . . ?
N3 Mn1 O1 C9 8.4(3) 3_656 . . . ?
N3 Mn1 O1 C9 -156.5(2) . . . . ?
N1 Mn1 O1 C9 -25.8(5) . . . . ?
N1 Mn1 O1 C9 -85.3(2) 3_656 . . . ?
O1 Mn1 N1 C1 -139.9(3) . . . . ?
O1 Mn1 N1 C1 91.1(2) 3_656 . . . ?
N3 Mn1 N1 C1 -175.7(2) 3_656 . . . ?
N3 Mn1 N1 C1 -9.1(2) . . . . ?
N1 Mn1 N1 C1 -79.52(19) 3_656 . . . ?
O1 Mn1 N1 C5 34.1(4) . . . . ?
O1 Mn1 N1 C5 -94.97(16) 3_656 . . . ?
N3 Mn1 N1 C5 -1.76(15) 3_656 . . . ?
N3 Mn1 N1 C5 164.80(16) . . . . ?
N1 Mn1 N1 C5 94.40(16) 3_656 . . . ?
C5 N1 C1 C2 0.5(4) . . . . ?
Mn1 N1 C1 C2 174.37(19) . . . . ?
N1 C1 C2 C3 -1.3(4) . . . . ?
C8 N2 N3 C6 -0.1(3) . . . . ?
C8 N2 N3 Mn1 172.42(19) . . . . ?
O1 Mn1 N3 C6 88.59(17) . . . . ?
O1 Mn1 N3 C6 -176.05(16) 3_656 . . . ?
N3 Mn1 N3 C6 -44.15(16) 3_656 . . . ?
N1 Mn1 N3 C6 -83.24(17) . . . . ?
N1 Mn1 N3 C6 -2.44(16) 3_656 . . . ?
O1 Mn1 N3 N2 -83.2(2) . . . . ?
O1 Mn1 N3 N2 12.2(2) 3_656 . . . ?
N3 Mn1 N3 N2 144.1(2) 3_656 . . . ?
N1 Mn1 N3 N2 105.0(2) . . . . ?
N1 Mn1 N3 N2 -174.2(2) 3_656 . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C1 N1 C5 C4 0.7(3) . . . . ?
Mn1 N1 C5 C4 -173.75(18) . . . . ?
C1 N1 C5 C6 179.7(2) . . . 3_656 ?
Mn1 N1 C5 C6 5.3(2) . . . 3_656 ?
C3 C4 C5 N1 -1.0(4) . . . . ?
C3 C4 C5 C6 179.9(2) . . . 3_656 ?
N2 N3 C6 C7 -0.2(3) . . . . ?
Mn1 N3 C6 C7 -174.20(16) . . . . ?
N2 N3 C6 C5 -179.77(19) . . . 3_656 ?
Mn1 N3 C6 C5 6.2(3) . . . 3_656 ?
N3 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C7 C8 179.9(2) 3_656 . . . ?
N3 N2 C8 C7 0.3(3) . . . . ?
C6 C7 C8 N2 -0.4(3) . . . . ?
Mn1 O1 C9 O2 -3.2(4) . . . . ?
Mn1 O1 C9 C10 176.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_e_c04
_database_code_depnum_ccdc_archive 'CCDC 1031998'
_audit_update_record             
;
2015-09-02 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 Cl2 Mn N3 O2'
_chemical_formula_sum            'C8 H11 Cl2 Mn N3 O2'
_chemical_formula_weight         307.04

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.642(2)
_cell_length_b                   19.420(4)
_cell_length_c                   11.223(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.100(4)
_cell_angle_gamma                90
_cell_volume                     2480.8(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4123
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.21

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.483
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.762982
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38802
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.789
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6087
_reflns_number_gt                4907
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
  The O-H hidrogen atoms where located in the diference Fourier map
 and refined with a constrained distance O-H of 0.850(1)Angstroms.

  ADPs of several C and N of the disordered moiety were constrained
 with the EADP instruction using as refernce those of the non
 disordered molecule.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+4.8587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6087
_refine_ls_number_parameters     341
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1337
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.013
_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 0.43972(5) 0.31575(3) 0.29460(5) 0.03978(16) Uani 1 1 d . . . . .
Cl1 Cl 0.36318(9) 0.20068(5) 0.33271(11) 0.0520(3) Uani 1 1 d . . . . .
N3 N 0.2985(3) 0.36541(17) 0.3754(3) 0.0465(8) Uani 1 1 d . . . . .
C8 C 0.1478(4) 0.3959(3) 0.4575(4) 0.0560(11) Uani 1 1 d . . . . .
H8 H 0.0810 0.3927 0.4905 0.067 Uiso 1 1 calc R U . . .
Cl2 Cl 0.60283(9) 0.29309(7) 0.18578(11) 0.0614(3) Uani 1 1 d . . . . .
N2 N 0.2033(3) 0.3435(2) 0.4157(4) 0.0595(10) Uani 1 1 d . . . . .
H2N H 0.1811 0.3012 0.4148 0.071 Uiso 1 1 calc R U . . .
C7 C 0.2075(4) 0.4549(2) 0.4427(4) 0.0537(11) Uani 1 1 d . . . . .
H7 H 0.1899 0.4996 0.4627 0.064 Uiso 1 1 calc R U . . .
O1 O 0.33280(18) 0.3303(2) 0.1082(2) 0.0646(9) Uani 1 1 d D . . . .
H1B H 0.3688(4) 0.329(3) 0.0497(3) 0.097 Uiso 1 1 d D U . . .
H1C H 0.2609(3) 0.3199(7) 0.083(2) 0.097 Uiso 1 1 d D U . . .
N1 N 0.4724(3) 0.43249(17) 0.3058(3) 0.0445(8) Uani 1 1 d . . . . .
C6 C 0.3014(4) 0.4332(2) 0.3905(3) 0.0417(8) Uani 1 1 d . . . . .
C5 C 0.3963(4) 0.47062(19) 0.3537(3) 0.0435(8) Uani 1 1 d . . . . .
O2 O 0.5704(2) 0.30635(14) 0.4665(2) 0.0660(9) Uani 1 1 d D . . . .
H2B H 0.6403(3) 0.3217(4) 0.482(6) 0.099 Uiso 1 1 d D U . . .
H2C H 0.5681(15) 0.2756(2) 0.5199(4) 0.099 Uiso 1 1 d D U . . .
C4 C 0.4079(4) 0.5413(2) 0.3678(4) 0.0521(10) Uani 1 1 d . . . . .
H4 H 0.3544 0.5665 0.4011 0.063 Uiso 1 1 calc R U . . .
C3 C 0.4999(4) 0.5733(3) 0.3315(4) 0.0602(12) Uani 1 1 d . . . . .
H3 H 0.5101 0.6206 0.3411 0.072 Uiso 1 1 calc R U . . .
C2 C 0.5772(4) 0.5351(3) 0.2808(5) 0.0625(13) Uani 1 1 d . . . . .
H2 H 0.6390 0.5562 0.2543 0.075 Uiso 1 1 calc R U . . .
C1 C 0.5606(4) 0.4651(3) 0.2704(5) 0.0617(10) Uani 1 1 d . . . . .
H1 H 0.6133 0.4392 0.2370 0.074 Uiso 1 1 calc R U . . .
Mn1A Mn 0.05540(5) 0.67187(3) 0.23622(6) 0.04297(16) Uani 1 1 d . . . . .
O1A O -0.0979(2) 0.70069(16) 0.3032(2) 0.0669(10) Uani 1 1 d D . . . .
H1AA H -0.1673(3) 0.7094(8) 0.2645(9) 0.100 Uiso 1 1 d D U . . .
H1AB H -0.092(3) 0.7295(2) 0.3613(4) 0.100 Uiso 1 1 d D U . . .
O2A O 0.1306(2) 0.77232(16) 0.2136(2) 0.0651(9) Uani 1 1 d D . . . .
H2AA H 0.1271(18) 0.7904(4) 0.1440(3) 0.098 Uiso 1 1 d D U . . .
H2AB H 0.2030(3) 0.7764(16) 0.2466(12) 0.098 Uiso 1 1 d D U . . .
Cl1A Cl 0.15871(9) 0.65719(6) 0.45611(10) 0.0561(3) Uani 1 1 d . . . . .
C8A C 0.3351(5) 0.5907(4) 0.0523(5) 0.0826(18) Uani 1 1 d . . . . .
H8A H 0.3968 0.5920 0.0114 0.099 Uiso 1 1 calc R U . A 1
C1A C -0.0688(7) 0.5264(4) 0.2484(8) 0.0617(10) Uani 0.659(7) 1 d . . P B 1
H1A H -0.1182 0.5517 0.2871 0.074 Uiso 0.659(7) 1 calc R U P B 1
C3A C -0.0253(7) 0.4201(4) 0.1772(7) 0.064(2) Uani 0.659(7) 1 d . . P B 1
H3A H -0.0402 0.3734 0.1630 0.077 Uiso 0.659(7) 1 calc R U P B 1
C4A C 0.0682(6) 0.4525(3) 0.1379(6) 0.0487(17) Uani 0.659(7) 1 d . . P B 1
H4A H 0.1166 0.4272 0.0980 0.058 Uiso 0.659(7) 1 calc R U P B 1
C5A C 0.0887(7) 0.5255(3) 0.1597(6) 0.0435(8) Uani 0.659(7) 1 d . . P B 1
C6A C 0.1842(8) 0.5610(5) 0.1241(6) 0.0502(17) Uani 0.659(7) 1 d . . P B 1
C7A C 0.2724(8) 0.5385(5) 0.0636(7) 0.058(2) Uani 0.659(7) 1 d . . P B 1
H7A H 0.2825 0.4940 0.0372 0.070 Uiso 0.659(7) 1 calc R U P B 1
N2A N 0.2936(7) 0.6464(5) 0.1134(8) 0.058(2) Uani 0.659(7) 1 d . . P B 1
H2A H 0.3244 0.6869 0.1224 0.070 Uiso 0.659(7) 1 calc R U P B 1
N3A N 0.1983(7) 0.6262(4) 0.1554(7) 0.0446(16) Uani 0.659(7) 1 d . . P B 1
N1A N 0.0045(4) 0.55974(17) 0.2185(3) 0.0611(10) Uani 1 1 d G . . . .
N2' N -0.0888(5) 0.5310(2) 0.2658(7) 0.0595(10) Uani 0.341(7) 1 d G . P B 2
H2' H -0.1336 0.5529 0.3046 0.071 Uiso 0.341(7) 1 calc R U P B 2
C2A C -0.0950(5) 0.4596(2) 0.2378(5) 0.0757(15) Uani 1 1 d G . . B .
H2" H -0.1559 0.4405 0.2689 0.091 Uiso 1 1 calc R U . C 1
C3' C -0.0055(8) 0.4442(2) 0.1732(9) 0.0602(12) Uani 0.341(7) 1 d G . P B 2
H3' H 0.0101 0.4012 0.1439 0.072 Uiso 0.341(7) 1 calc R U P B 2
C5' C 0.0560(7) 0.5061(3) 0.1613(9) 0.0502(17) Uani 0.341(7) 1 d G . P B 2
C4' C 0.1995(13) 0.4886(8) 0.0707(12) 0.057(4) Uani 0.341(7) 1 d . . P B 2
H4' H 0.1744 0.4430 0.0628 0.068 Uiso 0.341(7) 1 calc R U P B 2
C6' C 0.1434(14) 0.5353(9) 0.1251(12) 0.0417(8) Uani 0.341(7) 1 d . . P B 2
C7' C 0.2931(16) 0.5094(10) 0.0277(15) 0.068(5) Uani 0.341(7) 1 d . . P B 2
H7'A H 0.3329 0.4795 -0.0142 0.082 Uiso 0.341(7) 1 calc R U P B 2
C1' C 0.2535(17) 0.6223(13) 0.091(2) 0.065(6) Uani 0.341(7) 1 d . . P B 2
H1' H 0.2563 0.6699 0.0844 0.078 Uiso 0.341(7) 1 calc R U P B 2
N3' N 0.1678(13) 0.6002(8) 0.1384(13) 0.043(3) Uani 0.341(7) 1 d . . P B 2
Cl2A Cl -0.07414(9) 0.69974(6) 0.02416(9) 0.0498(3) Uani 1 1 d . . . . .


_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 O2 2.200(2) . ?
Mn1 O1 2.217(2) . ?
Mn1 N3 2.254(3) . ?
Mn1 N1 2.298(3) . ?
Mn1 Cl1 2.4760(13) . ?
Mn1 Cl2 2.5025(13) . ?
N3 C6 1.326(5) . ?
N3 N2 1.351(5) . ?
C8 N2 1.342(6) . ?
C8 C7 1.369(7) . ?
C8 H8 0.9300 . ?
N2 H2N 0.8600 . ?
C7 C6 1.410(6) . ?
C7 H7 0.9300 . ?
O1 H1B 0.8500(3) . ?
O1 H1C 0.85000(19) . ?
N1 C1 1.336(6) . ?
N1 C5 1.350(5) . ?
C6 C5 1.453(6) . ?
C5 C4 1.385(6) . ?
O2 H2B 0.8500(4) . ?
O2 H2C 0.85000(16) . ?
C4 C3 1.372(6) . ?
C4 H4 0.9300 . ?
C3 C2 1.377(7) . ?
C3 H3 0.9300 . ?
C2 C1 1.374(7) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
Mn1A O1A 2.151(3) . ?
Mn1A O2A 2.175(3) . ?
Mn1A N3A 2.238(8) . ?
Mn1A N1A 2.254(3) . ?
Mn1A N3' 2.336(17) . ?
Mn1A Cl1A 2.5245(13) . ?
Mn1A Cl2A 2.5935(12) . ?
O1A H1AA 0.85000(18) . ?
O1A H1AB 0.85000(18) . ?
O2A H2AA 0.85000(18) . ?
O2A H2AB 0.8500(2) . ?
C8A C7A 1.271(11) . ?
C8A C1' 1.28(3) . ?
C8A N2A 1.420(11) . ?
C8A C7' 1.66(2) . ?
C8A H8A 0.9300 . ?
C1A N1A 1.175(9) . ?
C1A C2A 1.334(9) . ?
C1A H1A 0.9300 . ?
C3A C2A 1.393(11) . ?
C3A C4A 1.406(10) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.449(9) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.434(11) . ?
C5A N1A 1.452(9) . ?
C6A N3A 1.315(10) . ?
C6A C7A 1.414(13) . ?
C7A H7A 0.9300 . ?
N2A N3A 1.352(10) . ?
N2A H2A 0.8600 . ?
N1A N2' 1.4200 . ?
N1A C5' 1.4200 . ?
N2' C2A 1.4200 . ?
N2' H2' 0.8600 . ?
C2A C3' 1.4200 . ?
C2A H2" 0.9300 . ?
C3' C5' 1.4200 . ?
C3' H3' 0.9300 . ?
C5' C6' 1.302(18) . ?
C4' C6' 1.338(19) . ?
C4' C7' 1.34(2) . ?
C4' H4' 0.9300 . ?
C6' N3' 1.294(18) . ?
C7' H7'A 0.9300 . ?
C1' N3' 1.30(2) . ?
C1' H1' 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
O2 Mn1 O1 170.58(10) . . ?
O2 Mn1 N3 96.38(12) . . ?
O1 Mn1 N3 90.73(11) . . ?
O2 Mn1 N1 87.58(11) . . ?
O1 Mn1 N1 88.84(13) . . ?
N3 Mn1 N1 71.49(12) . . ?
O2 Mn1 Cl1 88.93(7) . . ?
O1 Mn1 Cl1 97.29(10) . . ?
N3 Mn1 Cl1 89.85(9) . . ?
N1 Mn1 Cl1 160.48(10) . . ?
O2 Mn1 Cl2 87.56(8) . . ?
O1 Mn1 Cl2 83.98(7) . . ?
N3 Mn1 Cl2 164.50(10) . . ?
N1 Mn1 Cl2 93.79(10) . . ?
Cl1 Mn1 Cl2 105.24(5) . . ?
C6 N3 N2 105.8(3) . . ?
C6 N3 Mn1 118.3(3) . . ?
N2 N3 Mn1 135.9(3) . . ?
N2 C8 C7 107.4(4) . . ?
N2 C8 H8 126.3 . . ?
C7 C8 H8 126.3 . . ?
C8 N2 N3 111.5(4) . . ?
C8 N2 H2N 124.2 . . ?
N3 N2 H2N 124.2 . . ?
C8 C7 C6 104.9(4) . . ?
C8 C7 H7 127.5 . . ?
C6 C7 H7 127.5 . . ?
Mn1 O1 H1B 117.1(7) . . ?
Mn1 O1 H1C 127.3(17) . . ?
H1B O1 H1C 110.1(18) . . ?
C1 N1 C5 117.9(4) . . ?
C1 N1 Mn1 125.5(3) . . ?
C5 N1 Mn1 116.6(3) . . ?
N3 C6 C7 110.4(4) . . ?
N3 C6 C5 117.5(4) . . ?
C7 C6 C5 132.1(4) . . ?
N1 C5 C4 122.2(4) . . ?
N1 C5 C6 116.1(3) . . ?
C4 C5 C6 121.7(4) . . ?
Mn1 O2 H2B 127(4) . . ?
Mn1 O2 H2C 124.0(9) . . ?
H2B O2 H2C 106(3) . . ?
C3 C4 C5 118.6(5) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C1 C2 C3 118.4(5) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
N1 C1 C2 123.1(5) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
O1A Mn1A O2A 101.03(12) . . ?
O1A Mn1A N3A 170.5(2) . . ?
O2A Mn1A N3A 87.5(2) . . ?
O1A Mn1A N1A 93.47(14) . . ?
O2A Mn1A N1A 163.90(14) . . ?
N3A Mn1A N1A 77.6(2) . . ?
O1A Mn1A N3' 155.1(4) . . ?
O2A Mn1A N3' 101.6(4) . . ?
N1A Mn1A N3' 63.0(4) . . ?
O1A Mn1A Cl1A 87.00(7) . . ?
O2A Mn1A Cl1A 95.41(7) . . ?
N3A Mn1A Cl1A 96.3(2) . . ?
N1A Mn1A Cl1A 92.28(10) . . ?
N3' Mn1A Cl1A 101.1(4) . . ?
O1A Mn1A Cl2A 84.33(7) . . ?
O2A Mn1A Cl2A 82.92(7) . . ?
N3A Mn1A Cl2A 92.8(2) . . ?
N1A Mn1A Cl2A 91.67(10) . . ?
N3' Mn1A Cl2A 88.2(4) . . ?
Cl1A Mn1A Cl2A 170.68(4) . . ?
Mn1A O1A H1AA 129.9(8) . . ?
Mn1A O1A H1AB 120(2) . . ?
H1AA O1A H1AB 100(2) . . ?
Mn1A O2A H2AA 122.3(7) . . ?
Mn1A O2A H2AB 115(2) . . ?
H2AA O2A H2AB 102.4(19) . . ?
C7A C8A N2A 107.4(7) . . ?
C1' C8A C7' 107.4(12) . . ?
C7A C8A H8A 126.3 . . ?
N2A C8A H8A 126.3 . . ?
N1A C1A C2A 132.6(8) . . ?
N1A C1A H1A 113.7 . . ?
C2A C1A H1A 113.7 . . ?
C2A C3A C4A 118.4(6) . . ?
C2A C3A H3A 120.8 . . ?
C4A C3A H3A 120.8 . . ?
C3A C4A C5A 119.7(7) . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A H4A 120.1 . . ?
C6A C5A C4A 122.2(8) . . ?
C6A C5A N1A 122.8(6) . . ?
C4A C5A N1A 115.0(6) . . ?
N3A C6A C7A 111.3(8) . . ?
N3A C6A C5A 116.7(8) . . ?
C7A C6A C5A 132.0(9) . . ?
C8A C7A C6A 107.0(8) . . ?
C8A C7A H7A 126.5 . . ?
C6A C7A H7A 126.5 . . ?
N3A N2A C8A 109.5(7) . . ?
N3A N2A H2A 125.3 . . ?
C8A N2A H2A 125.3 . . ?
C6A N3A N2A 104.7(8) . . ?
C6A N3A Mn1A 115.3(6) . . ?
N2A N3A Mn1A 139.4(6) . . ?
N2' N1A C5' 108.0 . . ?
C1A N1A C5A 118.5(6) . . ?
C1A N1A Mn1A 134.4(5) . . ?
N2' N1A Mn1A 123.7(3) . . ?
C5' N1A Mn1A 128.3(3) . . ?
C5A N1A Mn1A 107.1(3) . . ?
N1A N2' C2A 108.0 . . ?
N1A N2' H2' 126.0 . . ?
C2A N2' H2' 126.0 . . ?
C1A C2A C3A 115.7(6) . . ?
C3' C2A N2' 108.0 . . ?
C1A C2A H2" 122.2 . . ?
C3A C2A H2" 122.2 . . ?
C2A C3' C5' 108.0 . . ?
C2A C3' H3' 126.0 . . ?
C5' C3' H3' 126.0 . . ?
C6' C5' C3' 147.2(8) . . ?
C6' C5' N1A 104.7(8) . . ?
C3' C5' N1A 108.0 . . ?
C6' C4' C7' 118.0(17) . . ?
C6' C4' H4' 121.0 . . ?
C7' C4' H4' 121.0 . . ?
N3' C6' C5' 123.7(13) . . ?
N3' C6' C4' 126.7(17) . . ?
C5' C6' C4' 109.6(14) . . ?
C4' C7' C8A 117.4(14) . . ?
C4' C7' H7'A 121.3 . . ?
C8A C7' H7'A 121.3 . . ?
C8A C1' N3' 132(2) . . ?
C8A C1' H1' 114.0 . . ?
N3' C1' H1' 114.0 . . ?
C6' N3' C1' 116.3(18) . . ?
C6' N3' Mn1A 120.2(11) . . ?
C1' N3' Mn1A 123.4(15) . . ?

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
C7 C8 N2 N3 0.9(5) . . . . ?
C6 N3 N2 C8 -1.0(5) . . . . ?
Mn1 N3 N2 C8 179.3(3) . . . . ?
N2 C8 C7 C6 -0.4(5) . . . . ?
N2 N3 C6 C7 0.8(5) . . . . ?
Mn1 N3 C6 C7 -179.5(3) . . . . ?
N2 N3 C6 C5 -179.9(3) . . . . ?
Mn1 N3 C6 C5 -0.1(5) . . . . ?
C8 C7 C6 N3 -0.3(5) . . . . ?
C8 C7 C6 C5 -179.5(4) . . . . ?
C1 N1 C5 C4 -0.6(6) . . . . ?
Mn1 N1 C5 C4 178.6(3) . . . . ?
C1 N1 C5 C6 179.7(4) . . . . ?
Mn1 N1 C5 C6 -1.1(4) . . . . ?
N3 C6 C5 N1 0.8(5) . . . . ?
C7 C6 C5 N1 -180.0(4) . . . . ?
N3 C6 C5 C4 -178.9(4) . . . . ?
C7 C6 C5 C4 0.3(7) . . . . ?
N1 C5 C4 C3 0.1(6) . . . . ?
C6 C5 C4 C3 179.8(4) . . . . ?
C5 C4 C3 C2 0.9(7) . . . . ?
C4 C3 C2 C1 -1.3(7) . . . . ?
C5 N1 C1 C2 0.2(7) . . . . ?
Mn1 N1 C1 C2 -179.0(4) . . . . ?
C3 C2 C1 N1 0.7(8) . . . . ?
C2A C3A C4A C5A -0.8(10) . . . . ?
C3A C4A C5A C6A 178.6(6) . . . . ?
C3A C4A C5A N1A -2.3(9) . . . . ?
C4A C5A C6A N3A -176.0(7) . . . . ?
N1A C5A C6A N3A 5.0(10) . . . . ?
C4A C5A C6A C7A 1.2(12) . . . . ?
N1A C5A C6A C7A -177.8(7) . . . . ?
C1' C8A C7A C6A -8.6(12) . . . . ?
N2A C8A C7A C6A 4.3(8) . . . . ?
C7' C8A C7A C6A -173(2) . . . . ?
N3A C6A C7A C8A -3.6(9) . . . . ?
C5A C6A C7A C8A 179.0(7) . . . . ?
C7A C8A N2A N3A -3.8(9) . . . . ?
C1' C8A N2A N3A 24(2) . . . . ?
C7' C8A N2A N3A -2.0(13) . . . . ?
C7A C6A N3A N2A 1.2(9) . . . . ?
C5A C6A N3A N2A 178.9(6) . . . . ?
C7A C6A N3A Mn1A 174.4(5) . . . . ?
C5A C6A N3A Mn1A -7.8(9) . . . . ?
C8A N2A N3A C6A 1.5(9) . . . . ?
C8A N2A N3A Mn1A -169.1(6) . . . . ?
C2A C1A N1A N2' -173(4) . . . . ?
C2A C1A N1A C5' 2.3(14) . . . . ?
C2A C1A N1A C5A -1.4(14) . . . . ?
C2A C1A N1A Mn1A -178.7(6) . . . . ?
C6A C5A N1A C1A -177.5(8) . . . . ?
C4A C5A N1A C1A 3.4(9) . . . . ?
C6A C5A N1A N2' -175.4(5) . . . . ?
C4A C5A N1A N2' 5.5(9) . . . . ?
C6A C5A N1A C5' 172(2) . . . . ?
C4A C5A N1A C5' -6.6(14) . . . . ?
C6A C5A N1A Mn1A 0.5(7) . . . . ?
C4A C5A N1A Mn1A -178.6(4) . . . . ?
C1A N1A N2' C2A 5(3) . . . . ?
C5' N1A N2' C2A 0.0 . . . . ?
C5A N1A N2' C2A -4.7(8) . . . . ?
Mn1A N1A N2' C2A -179.9(3) . . . . ?
N1A C1A C2A C3A -1.8(14) . . . . ?
N1A C1A C2A C3' -2.2(14) . . . . ?
N1A C1A C2A N2' 174(3) . . . . ?
C4A C3A C2A C1A 2.8(10) . . . . ?
C4A C3A C2A C3' 3.9(14) . . . . ?
C4A C3A C2A N2' 1.6(12) . . . . ?
N1A N2' C2A C1A -4(2) . . . . ?
N1A N2' C2A C3A 0.9(9) . . . . ?
N1A N2' C2A C3' 0.0 . . . . ?
C1A C2A C3' C5' 0.9(5) . . . . ?
C3A C2A C3' C5' -178.1(19) . . . . ?
N2' C2A C3' C5' 0.0 . . . . ?
C2A C3' C5' C6' 175.1(17) . . . . ?
C2A C3' C5' N1A 0.0 . . . . ?
C1A N1A C5' C6' -178.3(8) . . . . ?
N2' N1A C5' C6' -177.3(9) . . . . ?
C5A N1A C5' C6' -7.2(13) . . . . ?
Mn1A N1A C5' C6' 2.6(11) . . . . ?
C1A N1A C5' C3' -1.0(6) . . . . ?
N2' N1A C5' C3' 0.0 . . . . ?
C5A N1A C5' C3' 170.1(17) . . . . ?
Mn1A N1A C5' C3' 179.9(4) . . . . ?
C3' C5' C6' N3' -177.7(10) . . . . ?
N1A C5' C6' N3' -2.4(17) . . . . ?
C3' C5' C6' C4' 4(2) . . . . ?
N1A C5' C6' C4' 179.2(10) . . . . ?
C7' C4' C6' N3' 2(2) . . . . ?
C7' C4' C6' C5' -179.7(12) . . . . ?
C6' C4' C7' C8A 3.1(19) . . . . ?
C7A C8A C7' C4' 5.1(11) . . . . ?
C1' C8A C7' C4' -11.5(18) . . . . ?
N2A C8A C7' C4' 1.1(19) . . . . ?
C7A C8A C1' N3' 11(2) . . . . ?
N2A C8A C1' N3' -142(5) . . . . ?
C7' C8A C1' N3' 19(3) . . . . ?
C5' C6' N3' C1' -176.1(15) . . . . ?
C4' C6' N3' C1' 2(2) . . . . ?
C5' C6' N3' Mn1A 2(2) . . . . ?
C4' C6' N3' Mn1A 179.6(11) . . . . ?
C8A C1' N3' C6' -15(3) . . . . ?
C8A C1' N3' Mn1A 167.3(16) . . . . ?

_refine_diff_density_max         1.029
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_e_c06
_database_code_depnum_ccdc_archive 'CCDC 1031999'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl Mn N4 O2'
_chemical_formula_sum            'C18 H14 Cl Mn N4 O2'
_chemical_formula_weight         408.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.183(4)
_cell_length_b                   7.422(3)
_cell_length_c                   18.732(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.061(6)
_cell_angle_gamma                90.00
_cell_volume                     1684.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3387
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.16

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.907691
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24962
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         28.33
_reflns_number_total             4154
_reflns_number_gt                2661
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
 N-H hydrogens refined freely
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4154
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.00899(3) 0.67167(6) 0.08830(2) 0.03356(14) Uani 1 1 d . . .
Cl1 Cl -0.00742(6) 0.96056(10) 0.14972(4) 0.0440(2) Uani 1 1 d . . .
O1 O -0.07552(15) 0.7087(3) 0.00140(10) 0.0427(5) Uani 1 1 d . . .
C1 C -0.1860(2) 0.7188(4) -0.01587(14) 0.0326(6) Uani 1 1 d . . .
N1 N -0.1215(2) 0.4974(4) 0.19262(15) 0.0461(7) Uani 1 1 d . . .
H1 H -0.068(2) 0.483(4) 0.2149(16) 0.044(10) Uiso 1 1 d . . .
O2 O 0.09921(14) 0.5546(3) 0.15914(10) 0.0398(5) Uani 1 1 d . . .
N2 N -0.12272(18) 0.5697(3) 0.12660(12) 0.0359(6) Uani 1 1 d . . .
C2 C -0.2223(2) 0.7859(4) -0.08384(15) 0.0389(7) Uani 1 1 d . . .
H2A H -0.1711 0.8236 -0.1142 0.047 Uiso 1 1 calc R . .
N3 N 0.1378(2) 0.8119(3) -0.02445(13) 0.0384(6) Uani 1 1 d . . .
H3 H 0.083(3) 0.838(4) -0.0463(17) 0.055(11) Uiso 1 1 d . . .
C3 C -0.3336(3) 0.7965(4) -0.10633(17) 0.0460(8) Uani 1 1 d . . .
H3A H -0.3570 0.8414 -0.1518 0.055 Uiso 1 1 calc R . .
N4 N 0.14051(18) 0.7393(3) 0.04154(12) 0.0324(5) Uani 1 1 d . . .
C4 C -0.4107(2) 0.7410(5) -0.06195(18) 0.0490(8) Uani 1 1 d . . .
H4A H -0.4857 0.7481 -0.0774 0.059 Uiso 1 1 calc R . .
C5 C -0.3758(2) 0.6752(4) 0.00524(17) 0.0436(7) Uani 1 1 d . . .
H5A H -0.4280 0.6382 0.0350 0.052 Uiso 1 1 calc R . .
C6 C -0.2628(2) 0.6625(4) 0.03004(14) 0.0324(6) Uani 1 1 d . . .
C7 C -0.2301(2) 0.5860(4) 0.10103(15) 0.0339(6) Uani 1 1 d . . .
C8 C -0.2941(2) 0.5208(4) 0.15237(17) 0.0469(8) Uani 1 1 d . . .
H8A H -0.3708 0.5149 0.1486 0.056 Uiso 1 1 calc R . .
C9 C -0.2229(3) 0.4670(5) 0.20947(17) 0.0503(8) Uani 1 1 d . . .
H9A H -0.2419 0.4182 0.2522 0.060 Uiso 1 1 calc R . .
C10 C 0.2073(2) 0.5749(4) 0.18109(15) 0.0349(7) Uani 1 1 d . . .
C11 C 0.2466(2) 0.4996(4) 0.24759(16) 0.0439(8) Uani 1 1 d . . .
H11A H 0.1986 0.4378 0.2743 0.053 Uiso 1 1 calc R . .
C12 C 0.3563(3) 0.5174(5) 0.27328(18) 0.0572(10) Uani 1 1 d . . .
H12A H 0.3819 0.4661 0.3172 0.069 Uiso 1 1 calc R . .
C13 C 0.4285(3) 0.6096(6) 0.23504(18) 0.0629(10) Uani 1 1 d . . .
H13A H 0.5018 0.6237 0.2536 0.076 Uiso 1 1 calc R . .
C14 C 0.3916(2) 0.6810(5) 0.16921(17) 0.0500(8) Uani 1 1 d . . .
H14A H 0.4410 0.7425 0.1434 0.060 Uiso 1 1 calc R . .
C15 C 0.2811(2) 0.6632(4) 0.14002(15) 0.0347(6) Uani 1 1 d . . .
C16 C 0.2476(2) 0.7339(4) 0.06816(15) 0.0326(6) Uani 1 1 d . . .
C17 C 0.3108(2) 0.8043(4) 0.01662(16) 0.0418(7) Uani 1 1 d . . .
H17A H 0.3872 0.8162 0.0205 0.050 Uiso 1 1 calc R . .
C18 C 0.2380(2) 0.8521(4) -0.04035(17) 0.0437(8) Uani 1 1 d . . .
H18A H 0.2556 0.9038 -0.0829 0.052 Uiso 1 1 calc R . .


_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 O2 1.8481(19) . ?
Mn1 O1 1.8522(19) . ?
Mn1 N4 1.970(2) . ?
Mn1 N2 1.976(2) . ?
Mn1 Cl1 2.4515(12) . ?
O1 C1 1.353(3) . ?
C1 C2 1.395(4) . ?
C1 C6 1.399(4) . ?
N1 C9 1.326(4) . ?
N1 N2 1.347(3) . ?
N1 H1 0.74(3) . ?
O2 C10 1.346(3) . ?
N2 C7 1.350(3) . ?
C2 C3 1.380(4) . ?
C2 H2A 0.9300 . ?
N3 C18 1.321(4) . ?
N3 N4 1.346(3) . ?
N3 H3 0.77(3) . ?
C3 C4 1.381(4) . ?
C3 H3A 0.9300 . ?
N4 C16 1.347(3) . ?
C4 C5 1.375(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.410(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.462(4) . ?
C7 C8 1.388(4) . ?
C8 C9 1.364(4) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 C11 1.402(4) . ?
C10 C15 1.406(4) . ?
C11 C12 1.378(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.374(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.373(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.405(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.462(4) . ?
C16 C17 1.398(4) . ?
C17 C18 1.361(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 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
O2 Mn1 O1 159.05(10) . . ?
O2 Mn1 N4 89.36(9) . . ?
O1 Mn1 N4 88.53(9) . . ?
O2 Mn1 N2 90.20(9) . . ?
O1 Mn1 N2 88.77(9) . . ?
N4 Mn1 N2 171.29(10) . . ?
O2 Mn1 Cl1 98.39(7) . . ?
O1 Mn1 Cl1 102.56(7) . . ?
N4 Mn1 Cl1 95.52(7) . . ?
N2 Mn1 Cl1 93.14(8) . . ?
C1 O1 Mn1 131.69(18) . . ?
O1 C1 C2 116.7(3) . . ?
O1 C1 C6 123.3(2) . . ?
C2 C1 C6 120.0(3) . . ?
C9 N1 N2 111.5(3) . . ?
C9 N1 H1 129(3) . . ?
N2 N1 H1 120(3) . . ?
C10 O2 Mn1 130.96(18) . . ?
N1 N2 C7 106.1(2) . . ?
N1 N2 Mn1 123.73(19) . . ?
C7 N2 Mn1 129.08(19) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C18 N3 N4 111.3(3) . . ?
C18 N3 H3 126(3) . . ?
N4 N3 H3 122(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
N3 N4 C16 106.3(2) . . ?
N3 N4 Mn1 124.60(18) . . ?
C16 N4 Mn1 128.98(19) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 122.7(2) . . ?
C5 C6 C7 119.2(3) . . ?
N2 C7 C8 108.5(3) . . ?
N2 C7 C6 121.2(2) . . ?
C8 C7 C6 130.3(3) . . ?
C9 C8 C7 106.7(3) . . ?
C9 C8 H8A 126.6 . . ?
C7 C8 H8A 126.6 . . ?
N1 C9 C8 107.2(3) . . ?
N1 C9 H9A 126.4 . . ?
C8 C9 H9A 126.4 . . ?
O2 C10 C11 117.3(3) . . ?
O2 C10 C15 123.1(2) . . ?
C11 C10 C15 119.6(3) . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
C14 C15 C10 118.2(3) . . ?
C14 C15 C16 119.2(3) . . ?
C10 C15 C16 122.6(2) . . ?
N4 C16 C17 108.4(3) . . ?
N4 C16 C15 121.1(3) . . ?
C17 C16 C15 130.5(3) . . ?
C18 C17 C16 106.2(3) . . ?
C18 C17 H17A 126.9 . . ?
C16 C17 H17A 126.9 . . ?
N3 C18 C17 107.8(3) . . ?
N3 C18 H18A 126.1 . . ?
C17 C18 H18A 126.1 . . ?

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
O2 Mn1 O1 C1 107.0(3) . . . . ?
N4 Mn1 O1 C1 -168.6(3) . . . . ?
N2 Mn1 O1 C1 19.6(2) . . . . ?
Cl1 Mn1 O1 C1 -73.3(2) . . . . ?
Mn1 O1 C1 C2 166.8(2) . . . . ?
Mn1 O1 C1 C6 -14.7(4) . . . . ?
O1 Mn1 O2 C10 106.1(3) . . . . ?
N4 Mn1 O2 C10 21.9(2) . . . . ?
N2 Mn1 O2 C10 -166.8(3) . . . . ?
Cl1 Mn1 O2 C10 -73.6(2) . . . . ?
C9 N1 N2 C7 0.2(4) . . . . ?
C9 N1 N2 Mn1 169.4(2) . . . . ?
O2 Mn1 N2 N1 16.7(2) . . . . ?
O1 Mn1 N2 N1 175.7(2) . . . . ?
N4 Mn1 N2 N1 103.8(6) . . . . ?
Cl1 Mn1 N2 N1 -81.8(2) . . . . ?
O2 Mn1 N2 C7 -176.8(3) . . . . ?
O1 Mn1 N2 C7 -17.7(3) . . . . ?
N4 Mn1 N2 C7 -89.7(7) . . . . ?
Cl1 Mn1 N2 C7 84.8(2) . . . . ?
O1 C1 C2 C3 178.4(3) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C18 N3 N4 C16 0.0(3) . . . . ?
C18 N3 N4 Mn1 176.7(2) . . . . ?
O2 Mn1 N4 N3 169.5(2) . . . . ?
O1 Mn1 N4 N3 10.3(2) . . . . ?
N2 Mn1 N4 N3 82.3(6) . . . . ?
Cl1 Mn1 N4 N3 -92.2(2) . . . . ?
O2 Mn1 N4 C16 -14.6(2) . . . . ?
O1 Mn1 N4 C16 -173.8(2) . . . . ?
N2 Mn1 N4 C16 -101.8(6) . . . . ?
Cl1 Mn1 N4 C16 83.7(2) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
O1 C1 C6 C5 -178.3(3) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
O1 C1 C6 C7 -0.4(4) . . . . ?
C2 C1 C6 C7 178.1(3) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 -178.0(3) . . . . ?
N1 N2 C7 C8 -0.5(3) . . . . ?
Mn1 N2 C7 C8 -168.9(2) . . . . ?
N1 N2 C7 C6 179.3(3) . . . . ?
Mn1 N2 C7 C6 10.9(4) . . . . ?
C1 C6 C7 N2 1.5(4) . . . . ?
C5 C6 C7 N2 179.4(3) . . . . ?
C1 C6 C7 C8 -178.6(3) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
N2 C7 C8 C9 0.6(4) . . . . ?
C6 C7 C8 C9 -179.2(3) . . . . ?
N2 N1 C9 C8 0.2(4) . . . . ?
C7 C8 C9 N1 -0.5(4) . . . . ?
Mn1 O2 C10 C11 164.2(2) . . . . ?
Mn1 O2 C10 C15 -17.2(4) . . . . ?
O2 C10 C11 C12 -179.4(3) . . . . ?
C15 C10 C11 C12 2.0(4) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 C14 -1.9(6) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 C14 C15 C10 2.0(5) . . . . ?
C13 C14 C15 C16 -176.9(3) . . . . ?
O2 C10 C15 C14 178.2(3) . . . . ?
C11 C10 C15 C14 -3.3(4) . . . . ?
O2 C10 C15 C16 -2.9(4) . . . . ?
C11 C10 C15 C16 175.7(3) . . . . ?
N3 N4 C16 C17 -0.3(3) . . . . ?
Mn1 N4 C16 C17 -176.76(19) . . . . ?
N3 N4 C16 C15 179.5(2) . . . . ?
Mn1 N4 C16 C15 3.0(4) . . . . ?
C14 C15 C16 N4 -172.0(3) . . . . ?
C10 C15 C16 N4 9.1(4) . . . . ?
C14 C15 C16 C17 7.8(5) . . . . ?
C10 C15 C16 C17 -171.1(3) . . . . ?
N4 C16 C17 C18 0.4(3) . . . . ?
C15 C16 C17 C18 -179.3(3) . . . . ?
N4 N3 C18 C17 0.3(3) . . . . ?
C16 C17 C18 N3 -0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_e_c07
_database_code_depnum_ccdc_archive 'CCDC 1032000'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Mn N8 O6, C4 H10 O'
_chemical_formula_sum            'C20 H24 Mn N8 O7'
_chemical_formula_weight         543.41

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.7494(16)
_cell_length_b                   11.6886(15)
_cell_length_c                   15.753(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.143(2)
_cell_angle_gamma                90
_cell_volume                     2338.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4182
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.35

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             1124
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.624
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.855514
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'sadabs v2.10 bruker 2001'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35946
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.152
_diffrn_reflns_theta_max         28.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5798
_reflns_number_gt                4920
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          SQUEEZE

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.004 0.750 258 54 ' '
2 0.750 -0.038 0.250 258 54 ' '
3 0.653 0.126 0.505 16 1 ' '
4 0.153 0.373 0.005 16 1 ' '
5 0.847 0.626 -0.005 16 1 ' '
6 0.347 0.873 0.495 16 1 ' '
_platon_squeeze_details          
;
 A considerable amount of electron density attibutable to an ethyl ether
 disordered solvent molecule per assymetric unit was removed with the SQUEEZE
 option of PLATON (Spek, A. L. (2011). PLATON, A Multipurpose Crystallographic
 Tool, Utrecht University, Utrecht, THe Netherlands.)
 Those solvent molecules are, however, included in the reported chemical formula
 and derived values (e.g. formula weight, F(000), etc).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+3.8650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5798
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.11834(3) 0.10079(3) 0.24507(2) 0.01492(12) Uani 1 1 d . . . . .
O1 O 0.25522(15) -0.01509(16) 0.27358(12) 0.0204(4) Uani 1 1 d . . . . .
N1 N -0.01097(17) 0.15378(19) 0.14443(14) 0.0177(4) Uani 1 1 d . . . . .
C1 C -0.0408(2) 0.2625(2) 0.12915(17) 0.0218(5) Uani 1 1 d . . . . .
H1A H -0.0046 0.3217 0.1611 0.026 Uiso 1 1 calc R U . . .
O2 O 0.26932(18) 0.09632(17) 0.38336(13) 0.0290(5) Uani 1 1 d . . . . .
N3 N 0.08291(19) -0.17131(19) 0.17431(15) 0.0192(4) Uani 1 1 d . . . . .
H3 H 0.138(3) -0.199(3) 0.204(2) 0.028(9) Uiso 1 1 d . . . . .
C2 C -0.1222(2) 0.2924(2) 0.06886(18) 0.0243(6) Uani 1 1 d . . . . .
H2A H -0.1397 0.3705 0.0585 0.029 Uiso 1 1 calc R U . . .
O3 O 0.4013(2) -0.0090(2) 0.3555(2) 0.0533(8) Uani 1 1 d . . . . .
N2 N 0.06266(17) -0.05797(19) 0.17103(14) 0.0174(4) Uani 1 1 d . . . . .
C3 C -0.1775(2) 0.2062(2) 0.02402(18) 0.0242(6) Uani 1 1 d . . . . .
H3A H -0.2348 0.2241 -0.0166 0.029 Uiso 1 1 calc R U . . .
N4 N 0.00364(17) 0.04500(19) 0.34275(14) 0.0182(4) Uani 1 1 d . . . . .
O4 O 0.25014(15) 0.21800(16) 0.21609(12) 0.0191(4) Uani 1 1 d . . . . .
C4 C -0.1478(2) 0.0932(2) 0.03963(17) 0.0209(5) Uani 1 1 d . . . . .
H4A H -0.1848 0.0324 0.0102 0.025 Uiso 1 1 calc R U . . .
N6 N 0.12287(18) 0.3627(2) 0.33704(15) 0.0201(5) Uani 1 1 d . . . . .
H6 H 0.164(3) 0.394(3) 0.299(2) 0.025(9) Uiso 1 1 d . . . . .
O5 O 0.37020(18) 0.2252(2) 0.12637(14) 0.0366(6) Uani 1 1 d . . . . .
C5 C -0.0630(2) 0.0705(2) 0.09892(15) 0.0161(5) Uani 1 1 d . . . . .
O6 O 0.23128(17) 0.11978(18) 0.09901(14) 0.0298(5) Uani 1 1 d . . . . .
N5 N 0.08515(17) 0.25584(18) 0.32638(14) 0.0173(4) Uani 1 1 d . . . . .
C6 C -0.0227(2) -0.0461(2) 0.11608(15) 0.0168(5) Uani 1 1 d . . . . .
N7 N 0.31023(18) 0.0242(2) 0.33958(14) 0.0210(5) Uani 1 1 d . . . . .
C7 C -0.0575(2) -0.1527(2) 0.08415(18) 0.0230(6) Uani 1 1 d . . . . .
H7A H -0.1161 -0.1678 0.0441 0.028 Uiso 1 1 calc R U . . .
N8 N 0.28504(18) 0.18791(19) 0.14504(14) 0.0188(4) Uani 1 1 d . . . . .
C8 C 0.0116(2) -0.2305(2) 0.12323(18) 0.0236(6) Uani 1 1 d . . . . .
H8A H 0.0096 -0.3111 0.1157 0.028 Uiso 1 1 calc R U . . .
C9 C -0.0426(2) -0.0576(2) 0.34527(17) 0.0218(5) Uani 1 1 d . . . . .
H9A H -0.0238 -0.1151 0.3067 0.026 Uiso 1 1 calc R U . . .
C10 C -0.1168(2) -0.0840(3) 0.40175(19) 0.0273(6) Uani 1 1 d . . . . .
H10A H -0.1480 -0.1578 0.4018 0.033 Uiso 1 1 calc R U . . .
C11 C -0.1443(2) -0.0009(3) 0.45766(18) 0.0287(6) Uani 1 1 d . . . . .
H11A H -0.1945 -0.0170 0.4970 0.034 Uiso 1 1 calc R U . . .
C12 C -0.0983(2) 0.1060(3) 0.45611(18) 0.0255(6) Uani 1 1 d . . . . .
H12A H -0.1167 0.1645 0.4939 0.031 Uiso 1 1 calc R U . . .
C13 C -0.0246(2) 0.1261(2) 0.39807(17) 0.0198(5) Uani 1 1 d . . . . .
C14 C 0.0283(2) 0.2372(2) 0.39240(17) 0.0198(5) Uani 1 1 d . . . . .
C15 C 0.0295(2) 0.3335(3) 0.44569(18) 0.0259(6) Uani 1 1 d . . . . .
H15A H -0.0044 0.3424 0.4966 0.031 Uiso 1 1 calc R U . . .
C16 C 0.0908(2) 0.4122(3) 0.40770(19) 0.0259(6) Uani 1 1 d . . . . .
H16A H 0.1075 0.4874 0.4276 0.031 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 2.2230(19) . ?
Mn1 O4 2.2465(18) . ?
Mn1 N1 2.269(2) . ?
Mn1 N2 2.272(2) . ?
Mn1 N5 2.281(2) . ?
Mn1 N4 2.310(2) . ?
O1 N7 1.286(3) . ?
N1 C1 1.342(3) . ?
N1 C5 1.348(3) . ?
C1 C2 1.387(4) . ?
C1 H1A 0.9500 . ?
O2 N7 1.234(3) . ?
N3 C8 1.349(4) . ?
N3 N2 1.350(3) . ?
N3 H3 0.86(4) . ?
C2 C3 1.387(4) . ?
C2 H2A 0.9500 . ?
O3 N7 1.228(3) . ?
N2 C6 1.335(3) . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9500 . ?
N4 C9 1.339(3) . ?
N4 C13 1.358(3) . ?
O4 N8 1.290(3) . ?
C4 C5 1.389(4) . ?
C4 H4A 0.9500 . ?
N6 N5 1.344(3) . ?
N6 C16 1.350(4) . ?
N6 H6 0.91(4) . ?
O5 N8 1.230(3) . ?
C5 C6 1.474(4) . ?
O6 N8 1.241(3) . ?
N5 C14 1.338(3) . ?
C6 C7 1.400(4) . ?
C7 C8 1.373(4) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 C10 1.390(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.377(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.470(4) . ?
C14 C15 1.403(4) . ?
C15 C16 1.379(4) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?

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 O4 79.90(7) . . ?
O1 Mn1 N1 144.66(7) . . ?
O4 Mn1 N1 101.62(8) . . ?
O1 Mn1 N2 79.02(7) . . ?
O4 Mn1 N2 126.79(7) . . ?
N1 Mn1 N2 71.95(8) . . ?
O1 Mn1 N5 123.55(7) . . ?
O4 Mn1 N5 79.01(7) . . ?
N1 Mn1 N5 90.90(8) . . ?
N2 Mn1 N5 150.74(8) . . ?
O1 Mn1 N4 103.05(8) . . ?
O4 Mn1 N4 146.86(7) . . ?
N1 Mn1 N4 94.52(8) . . ?
N2 Mn1 N4 85.65(8) . . ?
N5 Mn1 N4 71.93(8) . . ?
N7 O1 Mn1 107.87(15) . . ?
C1 N1 C5 118.0(2) . . ?
C1 N1 Mn1 124.09(18) . . ?
C5 N1 Mn1 117.83(17) . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1A 118.5 . . ?
C2 C1 H1A 118.5 . . ?
C8 N3 N2 111.3(2) . . ?
C8 N3 H3 127(2) . . ?
N2 N3 H3 122(2) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C6 N2 N3 105.6(2) . . ?
C6 N2 Mn1 116.56(17) . . ?
N3 N2 Mn1 137.08(17) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C9 N4 C13 117.7(2) . . ?
C9 N4 Mn1 125.40(18) . . ?
C13 N4 Mn1 116.76(17) . . ?
N8 O4 Mn1 109.43(14) . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
N5 N6 C16 111.7(2) . . ?
N5 N6 H6 120(2) . . ?
C16 N6 H6 128(2) . . ?
N1 C5 C4 122.4(2) . . ?
N1 C5 C6 115.1(2) . . ?
C4 C5 C6 122.5(2) . . ?
C14 N5 N6 105.5(2) . . ?
C14 N5 Mn1 116.63(17) . . ?
N6 N5 Mn1 136.60(17) . . ?
N2 C6 C7 110.7(2) . . ?
N2 C6 C5 117.7(2) . . ?
C7 C6 C5 131.5(2) . . ?
O3 N7 O2 122.7(2) . . ?
O3 N7 O1 119.3(2) . . ?
O2 N7 O1 118.0(2) . . ?
C8 C7 C6 105.0(2) . . ?
C8 C7 H7A 127.5 . . ?
C6 C7 H7A 127.5 . . ?
O5 N8 O6 122.7(2) . . ?
O5 N8 O4 119.4(2) . . ?
O6 N8 O4 117.8(2) . . ?
N3 C8 C7 107.4(2) . . ?
N3 C8 H8A 126.3 . . ?
C7 C8 H8A 126.3 . . ?
N4 C9 C10 122.9(3) . . ?
N4 C9 H9A 118.5 . . ?
C10 C9 H9A 118.5 . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10A 120.7 . . ?
C9 C10 H10A 120.7 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C11 C12 C13 118.5(3) . . ?
C11 C12 H12A 120.7 . . ?
C13 C12 H12A 120.7 . . ?
N4 C13 C12 122.6(3) . . ?
N4 C13 C14 115.4(2) . . ?
C12 C13 C14 122.0(3) . . ?
N5 C14 C15 110.9(2) . . ?
N5 C14 C13 118.3(2) . . ?
C15 C14 C13 130.8(3) . . ?
C16 C15 C14 104.6(2) . . ?
C16 C15 H15A 127.7 . . ?
C14 C15 H15A 127.7 . . ?
N6 C16 C15 107.3(3) . . ?
N6 C16 H16A 126.4 . . ?
C15 C16 H16A 126.4 . . ?

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 -0.1(4) . . . . ?
Mn1 N1 C1 C2 -178.1(2) . . . . ?
N1 C1 C2 C3 2.0(4) . . . . ?
C8 N3 N2 C6 -0.5(3) . . . . ?
C8 N3 N2 Mn1 168.3(2) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C1 N1 C5 C4 -2.3(4) . . . . ?
Mn1 N1 C5 C4 175.84(19) . . . . ?
C1 N1 C5 C6 177.2(2) . . . . ?
Mn1 N1 C5 C6 -4.7(3) . . . . ?
C3 C4 C5 N1 2.7(4) . . . . ?
C3 C4 C5 C6 -176.7(2) . . . . ?
C16 N6 N5 C14 -0.4(3) . . . . ?
C16 N6 N5 Mn1 -166.2(2) . . . . ?
N3 N2 C6 C7 0.2(3) . . . . ?
Mn1 N2 C6 C7 -171.39(17) . . . . ?
N3 N2 C6 C5 -179.4(2) . . . . ?
Mn1 N2 C6 C5 9.0(3) . . . . ?
N1 C5 C6 N2 -2.9(3) . . . . ?
C4 C5 C6 N2 176.5(2) . . . . ?
N1 C5 C6 C7 177.6(3) . . . . ?
C4 C5 C6 C7 -3.0(4) . . . . ?
Mn1 O1 N7 O3 -163.1(2) . . . . ?
Mn1 O1 N7 O2 15.3(3) . . . . ?
N2 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C8 179.8(3) . . . . ?
Mn1 O4 N8 O5 -165.1(2) . . . . ?
Mn1 O4 N8 O6 13.3(3) . . . . ?
N2 N3 C8 C7 0.7(3) . . . . ?
C6 C7 C8 N3 -0.6(3) . . . . ?
C13 N4 C9 C10 -0.3(4) . . . . ?
Mn1 N4 C9 C10 -175.3(2) . . . . ?
N4 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C9 N4 C13 C12 0.1(4) . . . . ?
Mn1 N4 C13 C12 175.6(2) . . . . ?
C9 N4 C13 C14 -179.8(2) . . . . ?
Mn1 N4 C13 C14 -4.4(3) . . . . ?
C11 C12 C13 N4 0.2(4) . . . . ?
C11 C12 C13 C14 -179.8(3) . . . . ?
N6 N5 C14 C15 0.1(3) . . . . ?
Mn1 N5 C14 C15 169.32(18) . . . . ?
N6 N5 C14 C13 179.5(2) . . . . ?
Mn1 N5 C14 C13 -11.3(3) . . . . ?
N4 C13 C14 N5 10.5(4) . . . . ?
C12 C13 C14 N5 -169.5(3) . . . . ?
N4 C13 C14 C15 -170.3(3) . . . . ?
C12 C13 C14 C15 9.8(5) . . . . ?
N5 C14 C15 C16 0.1(3) . . . . ?
C13 C14 C15 C16 -179.2(3) . . . . ?
N5 N6 C16 C15 0.4(3) . . . . ?
C14 C15 C16 N6 -0.3(3) . . . . ?

_refine_diff_density_max         1.033
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.093

_shelxl_version_number           2013-3

