# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_L_nosl25ab
_database_code_depnum_ccdc_archive 'CCDC 1544119'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;
#####################################################################  

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N2 O2'
_chemical_formula_sum            'C26 H24 N2 O2'
_chemical_formula_weight         396.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.834(3)
_cell_length_b                   5.070(2)
_cell_length_c                   19.480(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.32(3)
_cell_angle_gamma                90
_cell_volume                     965.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    749
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      69.95

_exptl_crystal_description       plate
_exptl_crystal_colour            yellowish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.685
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Oxford Diffraction, Xcalibur PX, Onyx'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_reflns_number            4845
_diffrn_reflns_av_unetI/netI     0.1341
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.524
_diffrn_reflns_theta_max         70.078
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             1751
_reflns_number_gt                718
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²] 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     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.0033(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1751
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
O1 O 0.1428(3) 0.6396(7) 0.52521(18) 0.0393(9) Uani 1 1 d . . . . .
N1 N 0.3313(3) 0.3454(9) 0.5155(2) 0.0362(11) Uani 1 1 d . . . . .
C1 C 0.1673(4) 0.6294(10) 0.5962(3) 0.0334(13) Uani 1 1 d . . . . .
C2 C 0.0923(4) 0.8114(11) 0.6328(3) 0.0366(13) Uani 1 1 d . . . . .
H2 H 0.0297 0.9300 0.6084 0.044 Uiso 1 1 calc R U . . .
C3 C 0.1106(4) 0.8146(11) 0.7024(3) 0.0382(13) Uani 1 1 d . . . . .
H3 H 0.0608 0.9379 0.7265 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2021(4) 0.6392(11) 0.7406(3) 0.0359(13) Uani 1 1 d . . . . .
C5 C 0.2176(4) 0.6354(11) 0.8126(3) 0.0402(13) Uani 1 1 d . . . . .
H5 H 0.1671 0.7570 0.8369 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3043(4) 0.4601(11) 0.8495(3) 0.0432(14) Uani 1 1 d . . . . .
H6 H 0.3138 0.4594 0.8986 0.052 Uiso 1 1 calc R U . . .
C7 C 0.3784(4) 0.2818(11) 0.8125(3) 0.0411(14) Uani 1 1 d . . . . .
H7 H 0.4396 0.1613 0.8372 0.049 Uiso 1 1 calc R U . . .
C8 C 0.3648(4) 0.2780(12) 0.7429(3) 0.0415(14) Uani 1 1 d . . . . .
H8 H 0.4153 0.1533 0.7196 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2762(4) 0.4570(10) 0.7037(3) 0.0329(12) Uani 1 1 d . . . . .
C10 C 0.2594(4) 0.4561(10) 0.6303(3) 0.0315(12) Uani 1 1 d . . . . .
C11 C 0.3410(4) 0.2757(11) 0.5889(3) 0.0369(13) Uani 1 1 d . . . . .
H11A H 0.4382 0.2816 0.6085 0.044 Uiso 1 1 calc R U . . .
H11B H 0.3082 0.0926 0.5933 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4282(4) 0.5538(11) 0.5013(3) 0.0395(13) Uani 1 1 d . . . . .
H12A H 0.4301 0.6904 0.5377 0.047 Uiso 1 1 calc R U . . .
H12B H 0.3965 0.6383 0.4565 0.047 Uiso 1 1 calc R U . . .
C13 C 0.1941(4) 0.4114(11) 0.4922(3) 0.0419(14) Uani 1 1 d . . . . .
H13A H 0.1352 0.2585 0.5001 0.050 Uiso 1 1 calc R U . . .
H13B H 0.1868 0.4434 0.4418 0.050 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
O1 C1 1.378(6) . yes
O1 C13 1.442(6) . yes
N1 C13 1.415(6) . yes
N1 C11 1.466(6) . yes
N1 C12 1.469(6) . yes
C1 C10 1.379(6) . ?
C1 C2 1.421(6) . ?
C2 C3 1.348(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.417(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(7) . ?
C4 C9 1.420(6) . ?
C5 C6 1.378(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.409(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.347(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.421(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.422(7) . ?
C10 C11 1.508(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C12 1.520(8) 3_666 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C13 112.7(4) . . ?
C13 N1 C11 109.0(3) . . ?
C13 N1 C12 112.6(4) . . ?
C11 N1 C12 112.5(4) . . ?
O1 C1 C10 122.7(4) . . ?
O1 C1 C2 115.9(4) . . ?
C10 C1 C2 121.4(5) . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.9(5) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 122.0(5) . . ?
C5 C4 C9 119.7(5) . . ?
C3 C4 C9 118.3(5) . . ?
C6 C5 C4 121.7(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 118.2(5) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C8 C7 C6 121.6(5) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 121.3(5) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 117.5(5) . . ?
C4 C9 C10 120.1(4) . . ?
C8 C9 C10 122.4(5) . . ?
C1 C10 C9 118.7(4) . . ?
C1 C10 C11 119.3(4) . . ?
C9 C10 C11 122.0(4) . . ?
N1 C11 C10 113.2(4) . . ?
N1 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N1 C12 C12 111.8(6) . 3_666 ?
N1 C12 H12A 109.3 . . ?
C12 C12 H12A 109.3 3_666 . ?
N1 C12 H12B 109.3 . . ?
C12 C12 H12B 109.3 3_666 . ?
H12A C12 H12B 107.9 . . ?
N1 C13 O1 114.6(4) . . ?
N1 C13 H13A 108.6 . . ?
O1 C13 H13A 108.6 . . ?
N1 C13 H13B 108.6 . . ?
O1 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?

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
C13 O1 C1 C10 15.2(6) . . . . ?
C13 O1 C1 C2 -165.3(4) . . . . ?
O1 C1 C2 C3 -179.9(4) . . . . ?
C10 C1 C2 C3 -0.3(7) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
C2 C3 C4 C5 -177.6(5) . . . . ?
C2 C3 C4 C9 0.3(7) . . . . ?
C3 C4 C5 C6 178.4(4) . . . . ?
C9 C4 C5 C6 0.5(7) . . . . ?
C4 C5 C6 C7 0.1(7) . . . . ?
C5 C6 C7 C8 -0.9(7) . . . . ?
C6 C7 C8 C9 1.0(8) . . . . ?
C5 C4 C9 C8 -0.4(6) . . . . ?
C3 C4 C9 C8 -178.4(4) . . . . ?
C5 C4 C9 C10 178.9(4) . . . . ?
C3 C4 C9 C10 1.0(6) . . . . ?
C7 C8 C9 C4 -0.3(7) . . . . ?
C7 C8 C9 C10 -179.6(5) . . . . ?
O1 C1 C10 C9 -179.0(4) . . . . ?
C2 C1 C10 C9 1.5(6) . . . . ?
O1 C1 C10 C11 2.3(6) . . . . ?
C2 C1 C10 C11 -177.2(4) . . . . ?
C4 C9 C10 C1 -1.8(7) . . . . ?
C8 C9 C10 C1 177.5(4) . . . . ?
C4 C9 C10 C11 176.9(4) . . . . ?
C8 C9 C10 C11 -3.8(7) . . . . ?
C13 N1 C11 C10 -42.0(6) . . . . ?
C12 N1 C11 C10 83.8(4) . . . . ?
C1 C10 C11 N1 11.6(6) . . . . ?
C9 C10 C11 N1 -167.1(4) . . . . ?
C13 N1 C12 C12 -156.9(5) . . . 3_666 ?
C11 N1 C12 C12 79.4(6) . . . 3_666 ?
C11 N1 C13 O1 63.1(6) . . . . ?
C12 N1 C13 O1 -62.6(5) . . . . ?
C1 O1 C13 N1 -49.4(5) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_nos592ab
_database_code_depnum_ccdc_archive 'CCDC 1544123'
_audit_update_record             
;
2017-06-25 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 F2 Mn N2 O4, N O3'
_chemical_formula_sum            'C22 H26 F2 Mn N3 O7'
_chemical_formula_weight         537.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.561(3)
_cell_length_b                   11.639(4)
_cell_length_c                   12.617(5)
_cell_angle_alpha                83.10(3)
_cell_angle_beta                 79.14(3)
_cell_angle_gamma                72.49(3)
_cell_volume                     1174.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4048
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      37.30

_exptl_crystal_description       plate
_exptl_crystal_colour            tea-like
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.626
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Technologies Xcalibur R, Ruby'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            12582
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.843
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5110
_reflns_number_gt                4219
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond ver. 3.2k, (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.5981P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5110
_refine_ls_number_parameters     318
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_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 0.63475(4) 0.26990(3) 0.31554(3) 0.01702(10) Uani 1 1 d . . . . .
F1 F 0.02032(16) 0.25343(12) 0.74204(12) 0.0302(3) Uani 1 1 d . . . . .
F2 F 1.29469(17) 0.13578(12) -0.09268(12) 0.0318(3) Uani 1 1 d . . . . .
O1 O 0.59453(18) 0.18076(13) 0.44740(13) 0.0206(3) Uani 1 1 d . . . . .
O2 O 0.78489(19) 0.13817(13) 0.24404(13) 0.0216(3) Uani 1 1 d . . . . .
N1 N 0.4764(2) 0.42012(15) 0.37540(15) 0.0193(4) Uani 1 1 d . . . . .
N2 N 0.6607(2) 0.38174(15) 0.18469(15) 0.0200(4) Uani 1 1 d . . . . .
C1 C 0.4535(3) 0.20255(18) 0.51678(18) 0.0186(4) Uani 1 1 d . . . . .
C2 C 0.4207(3) 0.10827(19) 0.58928(19) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.5000 0.0310 0.5873 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2764(3) 0.1245(2) 0.66342(19) 0.0244(5) Uani 1 1 d . . . . .
H3 H 0.2553 0.0591 0.7108 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1627(3) 0.2383(2) 0.66744(19) 0.0225(5) Uani 1 1 d . . . . .
C5 C 0.1877(3) 0.3343(2) 0.60075(19) 0.0216(5) Uani 1 1 d . . . . .
H5 H 0.1081 0.4113 0.6064 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3339(3) 0.31789(18) 0.52284(18) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.3585(3) 0.42246(19) 0.45603(19) 0.0204(5) Uani 1 1 d . . . . .
H7 H 0.2821 0.4987 0.4727 0.024 Uiso 1 1 calc R U . . .
C8 C 0.4964(3) 0.53021(18) 0.30847(18) 0.0194(4) Uani 1 1 d . . . . .
H8 H 0.5997 0.5454 0.3220 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3537(3) 0.64510(18) 0.32941(19) 0.0218(5) Uani 1 1 d . . . . .
H9A H 0.3437 0.6675 0.4042 0.026 Uiso 1 1 calc R U . . .
H9B H 0.2482 0.6308 0.3217 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3856(3) 0.74773(19) 0.2489(2) 0.0258(5) Uani 1 1 d . . . . .
H10A H 0.4863 0.7661 0.2610 0.031 Uiso 1 1 calc R U . . .
H10B H 0.2908 0.8211 0.2611 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4089(3) 0.7143(2) 0.1323(2) 0.0266(5) Uani 1 1 d . . . . .
H11A H 0.4303 0.7820 0.0820 0.032 Uiso 1 1 calc R U . . .
H11B H 0.3061 0.7003 0.1188 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5545(3) 0.60025(19) 0.1108(2) 0.0235(5) Uani 1 1 d . . . . .
H12A H 0.5650 0.5778 0.0360 0.028 Uiso 1 1 calc R U . . .
H12B H 0.6590 0.6160 0.1186 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5250(3) 0.49741(18) 0.19080(18) 0.0195(4) Uani 1 1 d . . . . .
H13 H 0.4224 0.4807 0.1780 0.023 Uiso 1 1 calc R U . . .
C14 C 0.7779(3) 0.3595(2) 0.1035(2) 0.0266(5) Uani 1 1 d . . . . .
H14 H 0.7793 0.4214 0.0472 0.032 Uiso 1 1 calc R U . . .
C15 C 0.9088(3) 0.24619(18) 0.09159(18) 0.0206(5) Uani 1 1 d . . . . .
C16 C 1.0400(3) 0.2438(2) 0.00490(19) 0.0229(5) Uani 1 1 d . . . . .
H16 H 1.0415 0.3138 -0.0421 0.028 Uiso 1 1 calc R U . . .
C17 C 1.1650(3) 0.1390(2) -0.01024(19) 0.0222(5) Uani 1 1 d . . . . .
C18 C 1.1658(3) 0.03470(19) 0.0554(2) 0.0251(5) Uani 1 1 d . . . . .
H18 H 1.2535 -0.0373 0.0421 0.030 Uiso 1 1 calc R U . . .
C19 C 1.0374(3) 0.03667(19) 0.1405(2) 0.0228(5) Uani 1 1 d . . . . .
H19 H 1.0378 -0.0348 0.1858 0.027 Uiso 1 1 calc R U . . .
C20 C 0.9061(3) 0.14201(18) 0.16149(18) 0.0183(4) Uani 1 1 d . . . . .
O1M O 0.8485(2) 0.30615(15) 0.38073(14) 0.0296(4) Uani 1 1 d D . . . .
H1M H 0.9074 0.3484 0.3456 0.044 Uiso 1 1 d DR U . . .
C1M C 0.9595(3) 0.1986(3) 0.4304(3) 0.0420(7) Uani 1 1 d . . . . .
H1M1 H 0.8930 0.1569 0.4841 0.063 Uiso 1 1 calc R U . . .
H1M2 H 1.0352 0.2237 0.4659 0.063 Uiso 1 1 calc R U . . .
H1M3 H 1.0239 0.1440 0.3743 0.063 Uiso 1 1 calc R U . . .
O2M O 0.41708(19) 0.23751(14) 0.26135(14) 0.0256(4) Uani 1 1 d D . . . .
H2M H 0.3250 0.2904 0.2718 0.038 Uiso 1 1 d DR U . . .
C2M C 0.4232(4) 0.1599(3) 0.1815(3) 0.0420(7) Uani 1 1 d . . . . .
H2M1 H 0.4032 0.2075 0.1133 0.063 Uiso 1 1 calc R U . . .
H2M2 H 0.3379 0.1178 0.2052 0.063 Uiso 1 1 calc R U . . .
H2M3 H 0.5329 0.1006 0.1707 0.063 Uiso 1 1 calc R U . . .
N10 N 1.0746(2) 0.45901(16) 0.19649(16) 0.0217(4) Uani 1 1 d . . . . .
O10 O 1.1083(2) 0.39735(15) 0.28510(14) 0.0288(4) Uani 1 1 d . . . . .
O20 O 1.1890(2) 0.46327(17) 0.12133(15) 0.0359(4) Uani 1 1 d . . . . .
O30 O 0.9272(2) 0.51133(14) 0.18935(15) 0.0303(4) 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 1.8778(17) . ?
Mn1 O1 1.8834(18) . ?
Mn1 N1 1.9925(19) . ?
Mn1 N2 1.997(2) . ?
Mn1 O2M 2.2465(17) . ?
Mn1 O1M 2.3064(18) . ?
F1 C4 1.371(3) . ?
F2 C17 1.366(3) . ?
O1 C1 1.326(3) . ?
O2 C20 1.331(3) . ?
N1 C7 1.288(3) . ?
N1 C8 1.484(3) . ?
N2 C14 1.282(3) . ?
N2 C13 1.489(3) . ?
C1 C2 1.403(3) . ?
C1 C6 1.423(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.361(3) . ?
C5 C6 1.417(3) . ?
C6 C7 1.441(3) . ?
C8 C9 1.527(3) . ?
C8 C13 1.534(3) . ?
C9 C10 1.528(3) . ?
C10 C11 1.529(3) . ?
C11 C12 1.534(3) . ?
C12 C13 1.520(3) . ?
C14 C15 1.454(3) . ?
C15 C16 1.409(3) . ?
C15 C20 1.415(3) . ?
C16 C17 1.365(3) . ?
C17 C18 1.384(3) . ?
C18 C19 1.381(3) . ?
C19 C20 1.405(3) . ?
O1M C1M 1.477(3) . ?
O2M C2M 1.416(3) . ?
N10 O20 1.236(2) . ?
N10 O30 1.240(2) . ?
N10 O10 1.286(3) . ?

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 95.31(7) . . ?
O2 Mn1 N1 173.59(8) . . ?
O1 Mn1 N1 91.03(8) . . ?
O2 Mn1 N2 91.44(8) . . ?
O1 Mn1 N2 173.21(7) . . ?
N1 Mn1 N2 82.23(8) . . ?
O2 Mn1 O2M 92.29(7) . . ?
O1 Mn1 O2M 90.19(7) . . ?
N1 Mn1 O2M 86.73(7) . . ?
N2 Mn1 O2M 90.16(8) . . ?
O2 Mn1 O1M 90.35(7) . . ?
O1 Mn1 O1M 87.52(7) . . ?
N1 Mn1 O1M 90.87(7) . . ?
N2 Mn1 O1M 91.82(8) . . ?
O2M Mn1 O1M 176.65(6) . . ?
C1 O1 Mn1 125.93(14) . . ?
C20 O2 Mn1 126.91(13) . . ?
C7 N1 C8 122.90(18) . . ?
C7 N1 Mn1 124.54(15) . . ?
C8 N1 Mn1 112.19(14) . . ?
C14 N2 C13 122.5(2) . . ?
C14 N2 Mn1 125.59(16) . . ?
C13 N2 Mn1 111.95(14) . . ?
O1 C1 C2 118.82(19) . . ?
O1 C1 C6 123.3(2) . . ?
C2 C1 C6 117.9(2) . . ?
C3 C2 C1 121.9(2) . . ?
C2 C3 C4 118.7(2) . . ?
C5 C4 F1 119.4(2) . . ?
C5 C4 C3 122.5(2) . . ?
F1 C4 C3 118.1(2) . . ?
C4 C5 C6 119.2(2) . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 117.54(19) . . ?
C1 C6 C7 122.6(2) . . ?
N1 C7 C6 124.78(19) . . ?
N1 C8 C9 115.81(18) . . ?
N1 C8 C13 105.41(16) . . ?
C9 C8 C13 111.54(19) . . ?
C8 C9 C10 109.73(18) . . ?
C9 C10 C11 111.25(18) . . ?
C10 C11 C12 110.7(2) . . ?
C13 C12 C11 109.59(19) . . ?
N2 C13 C12 116.14(18) . . ?
N2 C13 C8 105.11(18) . . ?
C12 C13 C8 112.12(17) . . ?
N2 C14 C15 124.5(2) . . ?
C16 C15 C20 120.75(19) . . ?
C16 C15 C14 116.6(2) . . ?
C20 C15 C14 122.7(2) . . ?
C17 C16 C15 118.7(2) . . ?
C16 C17 F2 119.4(2) . . ?
C16 C17 C18 122.3(2) . . ?
F2 C17 C18 118.24(19) . . ?
C19 C18 C17 119.1(2) . . ?
C18 C19 C20 121.4(2) . . ?
O2 C20 C19 118.7(2) . . ?
O2 C20 C15 123.61(19) . . ?
C19 C20 C15 117.6(2) . . ?
C1M O1M Mn1 114.80(14) . . ?
C2M O2M Mn1 126.66(15) . . ?
O20 N10 O30 122.3(2) . . ?
O20 N10 O10 119.27(19) . . ?
O30 N10 O10 118.38(19) . . ?

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 -148.47(16) . . . . ?
N1 Mn1 O1 C1 30.59(16) . . . . ?
O2M Mn1 O1 C1 -56.15(16) . . . . ?
O1M Mn1 O1 C1 121.41(16) . . . . ?
O1 Mn1 O2 C20 -153.98(17) . . . . ?
N2 Mn1 O2 C20 25.39(18) . . . . ?
O2M Mn1 O2 C20 115.62(18) . . . . ?
O1M Mn1 O2 C20 -66.44(18) . . . . ?
Mn1 O1 C1 C2 157.41(16) . . . . ?
Mn1 O1 C1 C6 -23.6(3) . . . . ?
O1 C1 C2 C3 -179.9(2) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C3 C4 F1 -179.55(19) . . . . ?
F1 C4 C5 C6 -179.16(19) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C4 C5 C6 C7 -178.1(2) . . . . ?
O1 C1 C6 C5 -178.76(19) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
O1 C1 C6 C7 -2.1(3) . . . . ?
C2 C1 C6 C7 176.9(2) . . . . ?
C8 N1 C7 C6 179.7(2) . . . . ?
Mn1 N1 C7 C6 7.2(3) . . . . ?
C5 C6 C7 N1 -173.2(2) . . . . ?
C1 C6 C7 N1 10.1(3) . . . . ?
C7 N1 C8 C9 -9.0(3) . . . . ?
Mn1 N1 C8 C9 164.27(15) . . . . ?
C7 N1 C8 C13 -132.8(2) . . . . ?
Mn1 N1 C8 C13 40.46(19) . . . . ?
N1 C8 C9 C10 -175.56(18) . . . . ?
C13 C8 C9 C10 -55.0(2) . . . . ?
C8 C9 C10 C11 57.0(3) . . . . ?
C9 C10 C11 C12 -58.7(3) . . . . ?
C10 C11 C12 C13 57.0(3) . . . . ?
C14 N2 C13 C12 -15.2(3) . . . . ?
Mn1 N2 C13 C12 165.14(15) . . . . ?
C14 N2 C13 C8 -139.7(2) . . . . ?
Mn1 N2 C13 C8 40.61(19) . . . . ?
C11 C12 C13 N2 -176.53(18) . . . . ?
C11 C12 C13 C8 -55.7(2) . . . . ?
N1 C8 C13 N2 -50.9(2) . . . . ?
C9 C8 C13 N2 -177.33(16) . . . . ?
N1 C8 C13 C12 -177.89(17) . . . . ?
C9 C8 C13 C12 55.6(2) . . . . ?
C13 N2 C14 C15 -177.2(2) . . . . ?
Mn1 N2 C14 C15 2.5(3) . . . . ?
N2 C14 C15 C16 -171.2(2) . . . . ?
N2 C14 C15 C20 9.7(4) . . . . ?
C20 C15 C16 C17 -0.2(3) . . . . ?
C14 C15 C16 C17 -179.3(2) . . . . ?
C15 C16 C17 F2 -178.78(19) . . . . ?
C15 C16 C17 C18 1.1(4) . . . . ?
C16 C17 C18 C19 -1.1(4) . . . . ?
F2 C17 C18 C19 178.8(2) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
Mn1 O2 C20 C19 159.81(16) . . . . ?
Mn1 O2 C20 C15 -21.6(3) . . . . ?
C18 C19 C20 O2 179.4(2) . . . . ?
C18 C19 C20 C15 0.7(3) . . . . ?
C16 C15 C20 O2 -179.3(2) . . . . ?
C14 C15 C20 O2 -0.2(3) . . . . ?
C16 C15 C20 C19 -0.6(3) . . . . ?
C14 C15 C20 C19 178.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O2 0.95 2.41 3.296(3) 155.3 2_656
C9 H9B F1 0.99 2.51 3.319(3) 138.3 2_566
C12 H12A O20 0.99 2.58 3.327(3) 132.3 2_765
C12 H12B O30 0.99 2.53 3.345(3) 140.0 .
C13 H13 O20 1.00 2.32 3.306(3) 170.1 1_455
C14 H14 O20 0.95 2.39 3.320(3) 166.1 2_765
O1M H1M N10 0.84 2.60 3.420(3) 166.0 .
O1M H1M O10 0.84 1.96 2.762(3) 158.6 .
O1M H1M O30 0.84 2.58 3.310(3) 145.4 .
O2M H2M O10 0.84 1.89 2.723(3) 172.7 1_455

_refine_diff_density_max         0.686
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_2_nos473
_database_code_depnum_ccdc_archive 'CCDC 1544121'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;
#####################################################################


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H36 Mn2 N6 O4 S2'
_chemical_formula_sum            'C50 H36 Mn2 N6 O4 S2'
_chemical_formula_weight         958.85

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'
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                   8.418(4)
_cell_length_b                   9.004(4)
_cell_length_c                   14.787(4)
_cell_angle_alpha                96.34(3)
_cell_angle_beta                 92.01(3)
_cell_angle_gamma                103.59(4)
_cell_volume                     1080.6(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4177
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      36.80

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.736
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Kuma KM4-CCD, Sapphire2, large Be window'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            12754
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.868
_diffrn_reflns_theta_max         27.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5117
_reflns_number_gt                3580
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0880P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5117
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.46031(6) 0.63173(5) 0.42517(3) 0.02450(16) Uani 1 1 d . . . . .
O1 O 0.4000(3) 0.4673(2) 0.32965(13) 0.0262(5) Uani 1 1 d . . . . .
O2 O 0.3178(3) 0.5300(2) 0.50854(13) 0.0284(5) Uani 1 1 d . . . . .
N1 N 0.6552(3) 0.7254(3) 0.36223(15) 0.0242(6) Uani 1 1 d . . . . .
N2 N 0.5727(3) 0.7808(3) 0.53010(15) 0.0241(6) Uani 1 1 d . . . . .
C1 C 0.4646(4) 0.4448(3) 0.24984(19) 0.0261(7) Uani 1 1 d . . . . .
C2 C 0.3905(4) 0.3029(4) 0.1923(2) 0.0293(7) Uani 1 1 d . . . . .
H2 H 0.3000 0.2323 0.2124 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4491(4) 0.2687(4) 0.1090(2) 0.0309(7) Uani 1 1 d . . . . .
H3 H 0.3992 0.1735 0.0735 0.037 Uiso 1 1 calc R U . . .
C4 C 0.5827(4) 0.3711(4) 0.07363(19) 0.0272(7) Uani 1 1 d . . . . .
C5 C 0.6391(4) 0.3350(4) -0.0145(2) 0.0345(8) Uani 1 1 d . . . . .
H5 H 0.5887 0.2397 -0.0497 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7650(4) 0.4359(4) -0.0493(2) 0.0356(8) Uani 1 1 d . . . . .
H6 H 0.7995 0.4125 -0.1086 0.043 Uiso 1 1 calc R U . . .
C7 C 0.8413(4) 0.5748(4) 0.0053(2) 0.0331(7) Uani 1 1 d . . . . .
H7 H 0.9286 0.6447 -0.0180 0.040 Uiso 1 1 calc R U . . .
C8 C 0.7929(4) 0.6126(4) 0.0921(2) 0.0289(7) Uani 1 1 d . . . . .
H8 H 0.8480 0.7068 0.1271 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6615(4) 0.5116(4) 0.12917(19) 0.0263(7) Uani 1 1 d . . . . .
C10 C 0.6025(4) 0.5463(3) 0.22010(19) 0.0245(6) Uani 1 1 d . . . . .
C11 C 0.6944(4) 0.6781(3) 0.28031(19) 0.0253(6) Uani 1 1 d . . . . .
H11 H 0.7921 0.7362 0.2589 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7637(4) 0.8634(4) 0.4167(2) 0.0286(7) Uani 1 1 d . . . . .
H12A H 0.7297 0.9575 0.4041 0.034 Uiso 1 1 calc R U . . .
H12B H 0.8785 0.8738 0.4003 0.034 Uiso 1 1 calc R U . . .
C13 C 0.7497(4) 0.8427(4) 0.51807(19) 0.0266(7) Uani 1 1 d . . . . .
H13A H 0.8139 0.7700 0.5353 0.032 Uiso 1 1 calc R U . . .
H13B H 0.7912 0.9426 0.5566 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5094(4) 0.8140(3) 0.60733(19) 0.0250(6) Uani 1 1 d . . . . .
H14 H 0.5762 0.8888 0.6519 0.030 Uiso 1 1 calc R U . . .
C15 C 0.3440(4) 0.7438(3) 0.62909(19) 0.0235(6) Uani 1 1 d . . . . .
C16 C 0.2756(4) 0.8069(3) 0.71006(19) 0.0243(6) Uani 1 1 d . . . . .
C17 C 0.3539(4) 0.9498(4) 0.76401(19) 0.0271(7) Uani 1 1 d . . . . .
H17 H 0.4547 1.0087 0.7464 0.032 Uiso 1 1 calc R U . . .
C18 C 0.2852(4) 1.0039(4) 0.8415(2) 0.0333(8) Uani 1 1 d . . . . .
H18 H 0.3397 1.0989 0.8758 0.040 Uiso 1 1 calc R U . . .
C19 C 0.1349(5) 0.9192(4) 0.8700(2) 0.0356(8) Uani 1 1 d . . . . .
H19 H 0.0898 0.9555 0.9237 0.043 Uiso 1 1 calc R U . . .
C20 C 0.0556(4) 0.7830(4) 0.8183(2) 0.0317(7) Uani 1 1 d . . . . .
H20 H -0.0459 0.7265 0.8364 0.038 Uiso 1 1 calc R U . . .
C21 C 0.1224(4) 0.7249(4) 0.7380(2) 0.0273(7) Uani 1 1 d . . . . .
C22 C 0.0384(4) 0.5835(4) 0.6845(2) 0.0279(7) Uani 1 1 d . . . . .
H22 H -0.0644 0.5293 0.7023 0.033 Uiso 1 1 calc R U . . .
C23 C 0.1023(4) 0.5246(4) 0.6084(2) 0.0283(7) Uani 1 1 d . . . . .
H23 H 0.0429 0.4311 0.5743 0.034 Uiso 1 1 calc R U . . .
C24 C 0.2581(4) 0.6024(3) 0.57971(19) 0.0250(6) Uani 1 1 d . . . . .
S1 S 0.14033(11) 0.89327(10) 0.24708(5) 0.0345(2) Uani 1 1 d . . . . .
N3 N 0.3019(4) 0.7669(3) 0.37771(19) 0.0340(6) Uani 1 1 d . . . . .
C25 C 0.2323(4) 0.8156(4) 0.3218(2) 0.0279(7) 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 O1 1.892(2) . yes
Mn1 O2 1.906(2) . yes
Mn1 N1 1.975(3) . yes
Mn1 N2 1.986(3) . yes
Mn1 N3 2.153(3) . yes
O1 C1 1.332(4) . ?
O2 C24 1.351(3) . ?
N1 C11 1.318(4) . yes
N1 C12 1.490(4) . yes
N2 C13 1.487(4) . yes
N2 C14 1.311(4) . yes
C1 C10 1.415(5) . ?
C1 C2 1.448(4) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.431(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.433(4) . ?
C4 C9 1.433(4) . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.411(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.425(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.476(4) . ?
C10 C11 1.445(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.536(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.450(4) . ?
C14 H14 0.9500 . ?
C15 C24 1.415(4) . ?
C15 C16 1.463(4) . ?
C16 C21 1.427(4) . ?
C16 C17 1.437(4) . ?
C17 C18 1.394(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.419(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.431(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.435(4) . ?
C22 C23 1.372(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.437(4) . ?
C23 H23 0.9500 . ?
S1 C25 1.635(3) . ?
N3 C25 1.177(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O2 94.47(10) . . yes
O1 Mn1 N1 90.80(10) . . yes
O2 Mn1 N1 163.85(10) . . yes
O1 Mn1 N2 165.18(10) . . yes
O2 Mn1 N2 88.06(10) . . yes
N1 Mn1 N2 83.10(11) . . yes
O1 Mn1 N3 96.41(10) . . yes
O2 Mn1 N3 97.47(11) . . yes
N1 Mn1 N3 97.09(11) . . yes
N2 Mn1 N3 97.74(11) . . yes
C1 O1 Mn1 130.5(2) . . ?
C24 O2 Mn1 124.57(19) . . ?
C11 N1 C12 119.7(3) . . ?
C11 N1 Mn1 126.8(2) . . ?
C12 N1 Mn1 113.50(18) . . ?
C14 N2 C13 120.6(3) . . ?
C14 N2 Mn1 126.3(2) . . ?
C13 N2 Mn1 112.79(17) . . ?
O1 C1 C10 124.6(3) . . ?
O1 C1 C2 116.6(3) . . ?
C10 C1 C2 118.8(3) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 122.5(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 C9 118.4(3) . . ?
C5 C4 C9 120.1(3) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 118.3(3) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 117.4(3) . . ?
C8 C9 C10 123.3(3) . . ?
C4 C9 C10 119.3(3) . . ?
C1 C10 C11 120.7(3) . . ?
C1 C10 C9 120.0(3) . . ?
C11 C10 C9 119.1(3) . . ?
N1 C11 C10 126.0(3) . . ?
N1 C11 H11 117.0 . . ?
C10 C11 H11 117.0 . . ?
N1 C12 C13 108.0(3) . . ?
N1 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
N1 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
N2 C13 C12 106.3(2) . . ?
N2 C13 H13A 110.5 . . ?
C12 C13 H13A 110.5 . . ?
N2 C13 H13B 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
N2 C14 C15 124.2(3) . . ?
N2 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C24 C15 C14 119.8(3) . . ?
C24 C15 C16 119.7(3) . . ?
C14 C15 C16 119.9(3) . . ?
C21 C16 C17 117.1(3) . . ?
C21 C16 C15 119.4(3) . . ?
C17 C16 C15 123.5(3) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 118.7(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C21 121.6(3) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C16 C21 C20 120.1(3) . . ?
C16 C21 C22 118.7(3) . . ?
C20 C21 C22 121.1(3) . . ?
C23 C22 C21 121.9(3) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
O2 C24 C15 123.7(3) . . ?
O2 C24 C23 116.7(3) . . ?
C15 C24 C23 119.5(3) . . ?
C25 N3 Mn1 154.7(3) . . ?
N3 C25 S1 176.7(3) . . ?

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 -170.5(2) . . . . ?
N1 Mn1 O1 C1 -5.8(3) . . . . ?
N2 Mn1 O1 C1 -71.2(5) . . . . ?
N3 Mn1 O1 C1 91.4(3) . . . . ?
Mn1 O1 C1 C10 1.2(4) . . . . ?
Mn1 O1 C1 C2 178.56(19) . . . . ?
O1 C1 C2 C3 -179.5(3) . . . . ?
C10 C1 C2 C3 -2.0(4) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C3 C4 C5 -178.3(3) . . . . ?
C2 C3 C4 C9 2.5(4) . . . . ?
C3 C4 C5 C6 178.3(3) . . . . ?
C9 C4 C5 C6 -2.5(5) . . . . ?
C4 C5 C6 C7 1.9(5) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
C3 C4 C9 C8 -179.3(3) . . . . ?
C5 C4 C9 C8 1.5(4) . . . . ?
C3 C4 C9 C10 -0.3(4) . . . . ?
C5 C4 C9 C10 -179.5(3) . . . . ?
O1 C1 C10 C11 6.1(4) . . . . ?
C2 C1 C10 C11 -171.3(3) . . . . ?
O1 C1 C10 C9 -178.6(2) . . . . ?
C2 C1 C10 C9 4.1(4) . . . . ?
C8 C9 C10 C1 175.9(3) . . . . ?
C4 C9 C10 C1 -3.0(4) . . . . ?
C8 C9 C10 C11 -8.6(4) . . . . ?
C4 C9 C10 C11 172.5(3) . . . . ?
C12 N1 C11 C10 179.5(3) . . . . ?
Mn1 N1 C11 C10 -0.7(4) . . . . ?
C1 C10 C11 N1 -6.2(5) . . . . ?
C9 C10 C11 N1 178.4(3) . . . . ?
C11 N1 C12 C13 -149.4(3) . . . . ?
Mn1 N1 C12 C13 30.7(3) . . . . ?
C14 N2 C13 C12 -148.8(3) . . . . ?
Mn1 N2 C13 C12 37.5(3) . . . . ?
N1 C12 C13 N2 -42.7(3) . . . . ?
C13 N2 C14 C15 -171.9(3) . . . . ?
Mn1 N2 C14 C15 0.8(4) . . . . ?
N2 C14 C15 C24 19.4(4) . . . . ?
N2 C14 C15 C16 -169.5(3) . . . . ?
C24 C15 C16 C21 -0.2(4) . . . . ?
C14 C15 C16 C21 -171.3(2) . . . . ?
C24 C15 C16 C17 -179.7(3) . . . . ?
C14 C15 C16 C17 9.2(4) . . . . ?
C21 C16 C17 C18 1.6(4) . . . . ?
C15 C16 C17 C18 -178.9(3) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C20 -1.4(5) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
C17 C16 C21 C20 -2.0(4) . . . . ?
C15 C16 C21 C20 178.5(3) . . . . ?
C17 C16 C21 C22 178.5(3) . . . . ?
C15 C16 C21 C22 -1.0(4) . . . . ?
C19 C20 C21 C16 0.7(5) . . . . ?
C19 C20 C21 C22 -179.7(3) . . . . ?
C16 C21 C22 C23 0.9(4) . . . . ?
C20 C21 C22 C23 -178.6(3) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
Mn1 O2 C24 C15 -31.9(4) . . . . ?
Mn1 O2 C24 C23 151.6(2) . . . . ?
C14 C15 C24 O2 -3.6(4) . . . . ?
C16 C15 C24 O2 -174.7(2) . . . . ?
C14 C15 C24 C23 172.7(2) . . . . ?
C16 C15 C24 C23 1.6(4) . . . . ?
C22 C23 C24 O2 174.8(3) . . . . ?
C22 C23 C24 C15 -1.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 S1 0.95 2.96 3.874(4) 161.6 1_655
C14 H14 S1 0.95 2.95 3.863(4) 162.7 2_676

_refine_diff_density_max         0.891
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.128

####################################################################### 
# 
# 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_3_nos571
_database_code_depnum_ccdc_archive 'CCDC 1544122'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;
#####################################################################  

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H32 Mn N2 O4, N O3'
_chemical_formula_sum            'C30 H32 Mn N3 O7'
_chemical_formula_weight         601.52

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                   8.716(3)
_cell_length_b                   9.048(3)
_cell_length_c                   35.845(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.10(3)
_cell_angle_gamma                90
_cell_volume                     2815.6(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12863
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      36.81

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.522
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Kuma MK4-CCD, Sapphire2, large Be window'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            25136
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_theta_min         2.779
_diffrn_reflns_theta_max         36.890
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.618
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.618
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.618
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8784
_reflns_number_gt                6676
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0904P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8784
_refine_ls_number_parameters     389
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.095
_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 0.22857(3) 0.68072(3) 0.13573(2) 0.01814(9) Uani 1 1 d . . . . .
O1 O 0.02846(14) 0.60329(13) 0.13387(3) 0.0239(3) Uani 1 1 d . . . . .
O2 O 0.23745(14) 0.73578(14) 0.18642(3) 0.0247(3) Uani 1 1 d . . . . .
N1 N 0.24611(16) 0.62480(15) 0.08314(3) 0.0189(3) Uani 1 1 d . . . . .
N2 N 0.43925(16) 0.75336(15) 0.13236(3) 0.0205(3) Uani 1 1 d . . . . .
C1 C -0.03015(18) 0.49732(18) 0.11155(4) 0.0207(3) Uani 1 1 d . . . . .
C2 C -0.16271(19) 0.4252(2) 0.12319(4) 0.0236(3) Uani 1 1 d . . . . .
H2 H -0.2009 0.4525 0.1462 0.028 Uiso 1 1 calc R U . . .
C3 C -0.2357(2) 0.31772(19) 0.10179(4) 0.0239(3) Uani 1 1 d . . . . .
H3 H -0.3255 0.2729 0.1099 0.029 Uiso 1 1 calc R U . . .
C4 C -0.18036(19) 0.27102(18) 0.06751(4) 0.0210(3) Uani 1 1 d . . . . .
C5 C -0.2565(2) 0.15634(19) 0.04608(5) 0.0250(3) Uani 1 1 d . . . . .
H5 H -0.3464 0.1124 0.0544 0.030 Uiso 1 1 calc R U . . .
C6 C -0.2019(2) 0.10839(19) 0.01361(5) 0.0256(4) Uani 1 1 d . . . . .
H6 H -0.2522 0.0303 -0.0003 0.031 Uiso 1 1 calc R U . . .
C7 C -0.0710(2) 0.17542(19) 0.00109(5) 0.0253(4) Uani 1 1 d . . . . .
H7 H -0.0337 0.1431 -0.0217 0.030 Uiso 1 1 calc R U . . .
C8 C 0.00459(19) 0.28742(19) 0.02122(4) 0.0226(3) Uani 1 1 d . . . . .
H8 H 0.0934 0.3306 0.0121 0.027 Uiso 1 1 calc R U . . .
C9 C -0.04745(19) 0.33968(17) 0.05524(4) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.02909(18) 0.45573(18) 0.07781(4) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.15925(18) 0.52984(18) 0.06444(4) 0.0198(3) Uani 1 1 d . . . . .
H11 H 0.1836 0.5071 0.0398 0.024 Uiso 1 1 calc R U . . .
C12 C 0.37773(19) 0.69835(18) 0.06723(4) 0.0197(3) Uani 1 1 d . . . . .
H12 H 0.3491 0.8039 0.0622 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4330(2) 0.63306(19) 0.03157(4) 0.0218(3) Uani 1 1 d . . . . .
H13A H 0.3487 0.6352 0.0112 0.026 Uiso 1 1 calc R U . . .
H13B H 0.4652 0.5291 0.0359 0.026 Uiso 1 1 calc R U . . .
C14 C 0.5688(2) 0.7253(2) 0.02076(4) 0.0244(3) Uani 1 1 d . . . . .
H14A H 0.6037 0.6875 -0.0030 0.029 Uiso 1 1 calc R U . . .
H14B H 0.5359 0.8292 0.0168 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7016(2) 0.7185(2) 0.05143(4) 0.0252(3) Uani 1 1 d . . . . .
H15A H 0.7886 0.7789 0.0440 0.030 Uiso 1 1 calc R U . . .
H15B H 0.7376 0.6151 0.0546 0.030 Uiso 1 1 calc R U . . .
C16 C 0.65106(19) 0.7762(2) 0.08877(4) 0.0227(3) Uani 1 1 d . . . . .
H16A H 0.7355 0.7619 0.1088 0.027 Uiso 1 1 calc R U . . .
H16B H 0.6290 0.8834 0.0867 0.027 Uiso 1 1 calc R U . . .
C17 C 0.50823(19) 0.69502(18) 0.09900(4) 0.0203(3) Uani 1 1 d . . . . .
H17 H 0.5369 0.5894 0.1040 0.024 Uiso 1 1 calc R U . . .
C18 C 0.5092(2) 0.84752(18) 0.15517(4) 0.0214(3) Uani 1 1 d . . . . .
H18 H 0.6054 0.8844 0.1487 0.026 Uiso 1 1 calc R U . . .
C19 C 0.45470(19) 0.90135(18) 0.18927(4) 0.0208(3) Uani 1 1 d . . . . .
C20 C 0.54395(19) 1.01216(18) 0.21092(4) 0.0214(3) Uani 1 1 d . . . . .
C21 C 0.6682(2) 1.08983(19) 0.19736(5) 0.0254(3) Uani 1 1 d . . . . .
H21 H 0.6940 1.0727 0.1725 0.030 Uiso 1 1 calc R U . . .
C22 C 0.7522(2) 1.1898(2) 0.21965(6) 0.0328(4) Uani 1 1 d . . . . .
H22 H 0.8364 1.2397 0.2102 0.039 Uiso 1 1 calc R U . . .
C23 C 0.7154(2) 1.2191(3) 0.25610(6) 0.0387(5) Uani 1 1 d . . . . .
H23 H 0.7744 1.2885 0.2712 0.046 Uiso 1 1 calc R U . . .
C24 C 0.5953(2) 1.1483(2) 0.26992(5) 0.0342(4) Uani 1 1 d . . . . .
H24 H 0.5701 1.1696 0.2946 0.041 Uiso 1 1 calc R U . . .
C25 C 0.5066(2) 1.0427(2) 0.24787(4) 0.0254(3) Uani 1 1 d . . . . .
C26 C 0.3824(2) 0.9683(2) 0.26245(5) 0.0300(4) Uani 1 1 d . . . . .
H26 H 0.3596 0.9880 0.2874 0.036 Uiso 1 1 calc R U . . .
C27 C 0.2946(2) 0.8691(2) 0.24149(5) 0.0301(4) Uani 1 1 d . . . . .
H27 H 0.2104 0.8223 0.2518 0.036 Uiso 1 1 calc R U . . .
C28 C 0.3277(2) 0.83452(18) 0.20413(4) 0.0225(3) Uani 1 1 d . . . . .
O1M O 0.13512(17) 0.90530(14) 0.11937(4) 0.0369(3) Uani 1 1 d D . . . .
H1M H 0.1955 0.9621 0.1093 0.055 Uiso 1 1 d DR U . . .
C1M C 0.0192(3) 0.9740(3) 0.13954(8) 0.0475(6) Uani 1 1 d . . . . .
H1M1 H 0.0686 1.0340 0.1600 0.071 Uiso 1 1 calc R U . . .
H1M2 H -0.0444 0.8976 0.1499 0.071 Uiso 1 1 calc R U . . .
H1M3 H -0.0459 1.0372 0.1225 0.071 Uiso 1 1 calc R U . . .
O2M O 0.32117(15) 0.45693(14) 0.15447(3) 0.0305(3) Uani 1 1 d D . . . .
H2M H 0.3203 0.3897 0.1383 0.046 Uiso 1 1 d DR U . . .
C2M C 0.4513(2) 0.4379(2) 0.18096(5) 0.0375(5) Uani 1 1 d . . . . .
H2M1 H 0.5459 0.4505 0.1684 0.056 Uiso 1 1 calc R U . . .
H2M2 H 0.4493 0.3385 0.1918 0.056 Uiso 1 1 calc R U . . .
H2M3 H 0.4484 0.5116 0.2009 0.056 Uiso 1 1 calc R U . . .
N10 N 0.3467(3) 0.1858(2) 0.08884(5) 0.0283(5) Uani 0.925(5) 1 d D U P A 1
O10 O 0.2916(3) 0.18753(19) 0.12047(5) 0.0511(7) Uani 0.925(5) 1 d D . P A 1
O20 O 0.3494(4) 0.0693(2) 0.07073(6) 0.0644(7) Uani 0.925(5) 1 d D U P A 1
O30 O 0.3970(4) 0.3016(3) 0.07658(6) 0.0312(6) Uani 0.925(5) 1 d D U P A 1
N100 N 0.358(3) 0.1527(19) 0.0896(4) 0.047(9) Uiso 0.075(5) 1 d D U P A 2
O100 O 0.396(3) 0.129(3) 0.1242(4) 0.051(7) Uiso 0.075(5) 1 d D . P A 2
O200 O 0.2660(19) 0.0671(16) 0.0722(4) 0.015(4) Uiso 0.075(5) 1 d D U P A 2
O300 O 0.385(5) 0.275(3) 0.0766(7) 0.026(8) Uiso 0.075(5) 1 d D U P A 2


_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 1.8753(13) . yes
Mn1 O2 1.8791(12) . yes
Mn1 N2 1.9642(15) . yes
Mn1 N1 1.9710(13) . yes
Mn1 O1M 2.2476(14) . yes
Mn1 O2M 2.2597(14) . yes
O1 C1 1.3219(19) . ?
O2 C28 1.316(2) . ?
N1 C11 1.292(2) . yes
N1 C12 1.483(2) . yes
N2 C18 1.295(2) . yes
N2 C17 1.4826(19) . yes
C1 C10 1.408(2) . ?
C1 C2 1.421(2) . ?
C2 C3 1.361(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.423(2) . ?
C3 H3 0.9500 . ?
C4 C9 1.418(2) . ?
C4 C5 1.420(2) . ?
C5 C6 1.367(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.451(2) . ?
C10 C11 1.436(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.525(2) . ?
C12 C17 1.537(2) . ?
C12 H12 1.0000 . ?
C13 C14 1.526(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.525(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.537(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.518(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 1.0000 . ?
C18 C19 1.435(2) . ?
C18 H18 0.9500 . ?
C19 C28 1.407(2) . ?
C19 C20 1.451(2) . ?
C20 C21 1.413(2) . ?
C20 C25 1.419(2) . ?
C21 C22 1.374(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.357(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.424(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.414(3) . ?
C26 C27 1.361(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.430(2) . ?
C27 H27 0.9500 . ?
O1M C1M 1.435(3) . ?
O1M H1M 0.8394 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
O2M C2M 1.424(2) . ?
O2M H2M 0.8399 . ?
C2M H2M1 0.9800 . ?
C2M H2M2 0.9800 . ?
C2M H2M3 0.9800 . ?
N10 O30 1.232(3) . ?
N10 O20 1.239(3) . ?
N10 O10 1.270(3) . ?
N100 O300 1.233(3) . ?
N100 O200 1.241(3) . ?
N100 O100 1.271(3) . ?

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 O2 95.27(6) . . yes
O1 Mn1 N2 173.97(5) . . yes
O2 Mn1 N2 90.71(6) . . yes
O1 Mn1 N1 91.20(6) . . yes
O2 Mn1 N1 173.20(5) . . yes
N2 Mn1 N1 82.80(6) . . yes
O1 Mn1 O1M 90.81(6) . . yes
O2 Mn1 O1M 89.74(6) . . yes
N2 Mn1 O1M 90.03(6) . . yes
N1 Mn1 O1M 92.27(6) . . yes
O1 Mn1 O2M 88.99(6) . . yes
O2 Mn1 O2M 88.13(5) . . yes
N2 Mn1 O2M 90.40(6) . . yes
N1 Mn1 O2M 89.90(5) . . yes
O1M Mn1 O2M 177.83(5) . . yes
C1 O1 Mn1 126.92(10) . . ?
C28 O2 Mn1 128.16(10) . . ?
C11 N1 C12 122.44(13) . . ?
C11 N1 Mn1 125.10(11) . . ?
C12 N1 Mn1 112.38(10) . . ?
C18 N2 C17 122.79(14) . . ?
C18 N2 Mn1 124.85(12) . . ?
C17 N2 Mn1 112.26(10) . . ?
O1 C1 C10 124.21(15) . . ?
O1 C1 C2 115.83(14) . . ?
C10 C1 C2 119.95(15) . . ?
C3 C2 C1 120.92(15) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.44(16) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C9 C4 C5 120.49(15) . . ?
C9 C4 C3 119.10(15) . . ?
C5 C4 C3 120.41(16) . . ?
C6 C5 C4 120.76(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.38(16) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 121.06(16) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.39(16) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C8 116.92(15) . . ?
C4 C9 C10 119.44(14) . . ?
C8 C9 C10 123.63(15) . . ?
C1 C10 C11 121.51(14) . . ?
C1 C10 C9 119.13(14) . . ?
C11 C10 C9 119.30(14) . . ?
N1 C11 C10 125.53(14) . . ?
N1 C11 H11 117.2 . . ?
C10 C11 H11 117.2 . . ?
N1 C12 C13 117.45(13) . . ?
N1 C12 C17 104.67(12) . . ?
C13 C12 C17 110.22(13) . . ?
N1 C12 H12 108.0 . . ?
C13 C12 H12 108.0 . . ?
C17 C12 H12 108.0 . . ?
C12 C13 C14 108.12(13) . . ?
C12 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C15 C14 C13 110.56(13) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 110.86(14) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 110.52(14) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N2 C17 C16 114.99(13) . . ?
N2 C17 C12 105.32(13) . . ?
C16 C17 C12 112.36(13) . . ?
N2 C17 H17 108.0 . . ?
C16 C17 H17 108.0 . . ?
C12 C17 H17 108.0 . . ?
N2 C18 C19 126.02(16) . . ?
N2 C18 H18 117.0 . . ?
C19 C18 H18 117.0 . . ?
C28 C19 C18 120.50(15) . . ?
C28 C19 C20 119.81(14) . . ?
C18 C19 C20 119.18(15) . . ?
C21 C20 C25 118.09(15) . . ?
C21 C20 C19 123.42(14) . . ?
C25 C20 C19 118.49(15) . . ?
C22 C21 C20 120.83(17) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 120.88(19) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.02(18) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.82(17) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C20 119.95(15) . . ?
C26 C25 C24 120.69(16) . . ?
C20 C25 C24 119.35(17) . . ?
C27 C26 C25 121.42(15) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 120.71(17) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
O2 C28 C19 124.48(14) . . ?
O2 C28 C27 116.00(15) . . ?
C19 C28 C27 119.47(15) . . ?
C1M O1M Mn1 121.00(13) . . ?
C1M O1M H1M 116.6 . . ?
Mn1 O1M H1M 116.0 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
C2M O2M Mn1 123.30(12) . . ?
C2M O2M H2M 109.3 . . ?
Mn1 O2M H2M 117.5 . . ?
O2M C2M H2M1 109.5 . . ?
O2M C2M H2M2 109.5 . . ?
H2M1 C2M H2M2 109.5 . . ?
O2M C2M H2M3 109.5 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?
O30 N10 O20 120.8(2) . . ?
O30 N10 O10 118.9(2) . . ?
O20 N10 O10 120.3(2) . . ?
O300 N100 O200 120.5(5) . . ?
O300 N100 O100 118.3(4) . . ?
O200 N100 O100 119.3(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
O2 Mn1 O1 C1 -151.99(13) . . . . ?
N1 Mn1 O1 C1 25.91(13) . . . . ?
O1M Mn1 O1 C1 118.20(13) . . . . ?
O2M Mn1 O1 C1 -63.96(13) . . . . ?
O1 Mn1 O2 C28 -158.53(14) . . . . ?
N2 Mn1 O2 C28 22.28(14) . . . . ?
O1M Mn1 O2 C28 -67.74(15) . . . . ?
O2M Mn1 O2 C28 112.66(14) . . . . ?
Mn1 O1 C1 C10 -20.8(2) . . . . ?
Mn1 O1 C1 C2 160.18(11) . . . . ?
O1 C1 C2 C3 177.86(15) . . . . ?
C10 C1 C2 C3 -1.2(2) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C9 -0.8(2) . . . . ?
C2 C3 C4 C5 178.59(16) . . . . ?
C9 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C5 C6 -178.38(16) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C5 C4 C9 C8 -0.5(2) . . . . ?
C3 C4 C9 C8 178.94(15) . . . . ?
C5 C4 C9 C10 -179.45(14) . . . . ?
C3 C4 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C4 0.1(2) . . . . ?
C7 C8 C9 C10 179.05(15) . . . . ?
O1 C1 C10 C11 -1.4(2) . . . . ?
C2 C1 C10 C11 177.61(15) . . . . ?
O1 C1 C10 C9 -178.65(14) . . . . ?
C2 C1 C10 C9 0.4(2) . . . . ?
C4 C9 C10 C1 0.2(2) . . . . ?
C8 C9 C10 C1 -178.66(15) . . . . ?
C4 C9 C10 C11 -177.07(14) . . . . ?
C8 C9 C10 C11 4.0(2) . . . . ?
C12 N1 C11 C10 -179.22(14) . . . . ?
Mn1 N1 C11 C10 4.2(2) . . . . ?
C1 C10 C11 N1 9.6(3) . . . . ?
C9 C10 C11 N1 -173.21(15) . . . . ?
C11 N1 C12 C13 -14.3(2) . . . . ?
Mn1 N1 C12 C13 162.62(11) . . . . ?
C11 N1 C12 C17 -136.91(15) . . . . ?
Mn1 N1 C12 C17 40.03(14) . . . . ?
N1 C12 C13 C14 -179.52(13) . . . . ?
C17 C12 C13 C14 -59.81(17) . . . . ?
C12 C13 C14 C15 61.69(18) . . . . ?
C13 C14 C15 C16 -59.10(19) . . . . ?
C14 C15 C16 C17 53.76(19) . . . . ?
C18 N2 C17 C16 -12.2(2) . . . . ?
Mn1 N2 C17 C16 164.38(11) . . . . ?
C18 N2 C17 C12 -136.46(16) . . . . ?
Mn1 N2 C17 C12 40.13(14) . . . . ?
C15 C16 C17 N2 -173.45(14) . . . . ?
C15 C16 C17 C12 -53.00(19) . . . . ?
N1 C12 C17 N2 -49.98(15) . . . . ?
C13 C12 C17 N2 -177.15(13) . . . . ?
N1 C12 C17 C16 -175.87(13) . . . . ?
C13 C12 C17 C16 56.96(18) . . . . ?
C17 N2 C18 C19 -175.54(15) . . . . ?
Mn1 N2 C18 C19 8.3(2) . . . . ?
N2 C18 C19 C28 10.9(3) . . . . ?
N2 C18 C19 C20 -177.24(16) . . . . ?
C28 C19 C20 C21 -176.76(16) . . . . ?
C18 C19 C20 C21 11.4(2) . . . . ?
C28 C19 C20 C25 4.4(2) . . . . ?
C18 C19 C20 C25 -167.50(15) . . . . ?
C25 C20 C21 C22 1.3(3) . . . . ?
C19 C20 C21 C22 -177.62(16) . . . . ?
C20 C21 C22 C23 -1.0(3) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C21 C20 C25 C26 179.51(16) . . . . ?
C19 C20 C25 C26 -1.6(2) . . . . ?
C21 C20 C25 C24 -0.5(2) . . . . ?
C19 C20 C25 C24 178.42(16) . . . . ?
C23 C24 C25 C26 179.5(2) . . . . ?
C23 C24 C25 C20 -0.5(3) . . . . ?
C20 C25 C26 C27 -1.3(3) . . . . ?
C24 C25 C26 C27 178.72(19) . . . . ?
C25 C26 C27 C28 1.4(3) . . . . ?
Mn1 O2 C28 C19 -11.2(2) . . . . ?
Mn1 O2 C28 C27 171.36(13) . . . . ?
C18 C19 C28 O2 -10.0(3) . . . . ?
C20 C19 C28 O2 178.28(15) . . . . ?
C18 C19 C28 C27 167.40(16) . . . . ?
C20 C19 C28 C27 -4.4(2) . . . . ?
C26 C27 C28 O2 179.09(17) . . . . ?
C26 C27 C28 C19 1.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 O20 1.00 2.42 3.368(3) 158.0 1_565
C12 H12 O200 1.00 2.52 3.484(16) 161.0 1_565
C13 H13B O30 0.99 2.62 3.433(3) 139.3 .
O1M H1M N10 0.84 2.56 3.376(3) 165.1 1_565
O1M H1M O10 0.84 2.23 2.894(2) 136.4 1_565
O1M H1M O20 0.84 2.23 3.051(3) 165.0 1_565
O1M H1M N100 0.84 2.38 3.205(16) 169.8 1_565
O1M H1M O100 0.84 2.34 3.04(2) 141.6 1_565
O1M H1M O200 0.84 1.79 2.578(16) 156.1 1_565
O2M H2M N10 0.84 2.58 3.420(3) 174.4 .
O2M H2M O10 0.84 1.95 2.727(2) 154.2 .
O2M H2M O30 0.84 2.50 3.246(3) 148.9 .
O2M H2M O100 0.84 2.51 3.24(3) 146.3 .
O2M H2M O300 0.84 2.55 3.33(4) 154.7 .

_refine_diff_density_max         0.854
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_1_nos472ab
_database_code_depnum_ccdc_archive 'CCDC 1544120'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-07-27 downloaded from the CCDC.
;
#####################################################################  

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Mn N5 O2'
_chemical_formula_sum            'C24 H18 Mn N5 O2'
_chemical_formula_weight         463.37

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   10.088(3)
_cell_length_b                   11.208(3)
_cell_length_c                   34.421(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3891.9(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4633
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      31.91

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark pink'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.713
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Technologies Xcalibur R, Ruby'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            35670
_diffrn_reflns_av_unetI/netI     0.0777
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.340
_diffrn_reflns_theta_max         31.987
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6334
_reflns_number_gt                4133
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+2.6090P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6334
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.25581(3) 0.65691(3) 0.13889(2) 0.01411(10) Uani 1 1 d . . . . .
O1 O 0.34212(16) 0.75433(16) 0.17487(5) 0.0168(4) Uani 1 1 d . . . . .
O2 O 0.37607(16) 0.68515(16) 0.09818(5) 0.0175(4) Uani 1 1 d . . . . .
N1 N 0.1196(2) 0.61996(19) 0.17811(6) 0.0152(4) Uani 1 1 d . . . . .
N2 N 0.15141(19) 0.54924(19) 0.10612(6) 0.0152(4) Uani 1 1 d . . . . .
C1 C 0.3299(2) 0.7610(2) 0.21279(7) 0.0150(5) Uani 1 1 d . . . . .
C2 C 0.4234(2) 0.8358(2) 0.23201(7) 0.0175(5) Uani 1 1 d . . . . .
H2 H 0.4914 0.8735 0.2174 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4166(2) 0.8538(2) 0.27082(7) 0.0178(5) Uani 1 1 d . . . . .
H3 H 0.4799 0.9043 0.2830 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3176(2) 0.7993(2) 0.29361(7) 0.0165(5) Uani 1 1 d . . . . .
C5 C 0.3080(2) 0.8227(2) 0.33391(7) 0.0172(5) Uani 1 1 d . . . . .
H5 H 0.3667 0.8787 0.3455 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2162(2) 0.7662(2) 0.35655(7) 0.0191(5) Uani 1 1 d . . . . .
H6 H 0.2094 0.7840 0.3835 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1328(2) 0.6825(2) 0.33961(7) 0.0189(5) Uani 1 1 d . . . . .
H7 H 0.0710 0.6409 0.3554 0.023 Uiso 1 1 calc R U . . .
C8 C 0.1380(2) 0.6585(2) 0.30052(7) 0.0177(5) Uani 1 1 d . . . . .
H8 H 0.0796 0.6007 0.2898 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2281(2) 0.7180(2) 0.27600(7) 0.0156(5) Uani 1 1 d . . . . .
C10 C 0.2315(2) 0.7028(2) 0.23417(7) 0.0159(5) Uani 1 1 d . . . . .
C11 C 0.1264(2) 0.6400(2) 0.21485(7) 0.0164(5) Uani 1 1 d . . . . .
H11 H 0.0560 0.6108 0.2305 0.020 Uiso 1 1 calc R U . . .
C12 C 0.0020(2) 0.5673(2) 0.15986(7) 0.0167(5) Uani 1 1 d . . . . .
H12A H -0.0549 0.6307 0.1488 0.020 Uiso 1 1 calc R U . . .
H12B H -0.0503 0.5225 0.1793 0.020 Uiso 1 1 calc R U . . .
C13 C 0.0491(2) 0.4843(2) 0.12810(7) 0.0168(5) Uani 1 1 d . . . . .
H13A H 0.0866 0.4105 0.1395 0.020 Uiso 1 1 calc R U . . .
H13B H -0.0255 0.4622 0.1108 0.020 Uiso 1 1 calc R U . . .
C14 C 0.1725(2) 0.5258(2) 0.06992(7) 0.0174(5) Uani 1 1 d . . . . .
H14 H 0.1159 0.4687 0.0580 0.021 Uiso 1 1 calc R U . . .
C15 C 0.2727(2) 0.5775(2) 0.04613(7) 0.0158(5) Uani 1 1 d . . . . .
C16 C 0.2763(2) 0.5472(2) 0.00503(7) 0.0165(5) Uani 1 1 d . . . . .
C17 C 0.1866(3) 0.4679(2) -0.01280(8) 0.0210(5) Uani 1 1 d . . . . .
H17 H 0.1189 0.4320 0.0024 0.025 Uiso 1 1 calc R U . . .
C18 C 0.1948(3) 0.4415(3) -0.05163(8) 0.0228(6) Uani 1 1 d . . . . .
H18 H 0.1342 0.3865 -0.0628 0.027 Uiso 1 1 calc R U . . .
C19 C 0.2920(3) 0.4950(3) -0.07493(8) 0.0233(6) Uani 1 1 d . . . . .
H19 H 0.2963 0.4775 -0.1019 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3802(3) 0.5723(2) -0.05864(8) 0.0218(6) Uani 1 1 d . . . . .
H20 H 0.4459 0.6086 -0.0745 0.026 Uiso 1 1 calc R U . . .
C21 C 0.3757(3) 0.5993(2) -0.01874(7) 0.0185(5) Uani 1 1 d . . . . .
C22 C 0.4709(3) 0.6764(2) -0.00171(8) 0.0190(5) Uani 1 1 d . . . . .
H22 H 0.5381 0.7100 -0.0176 0.023 Uiso 1 1 calc R U . . .
C23 C 0.4685(2) 0.7034(2) 0.03680(7) 0.0190(5) Uani 1 1 d . . . . .
H23 H 0.5339 0.7551 0.0473 0.023 Uiso 1 1 calc R U . . .
C24 C 0.3687(2) 0.6548(2) 0.06150(7) 0.0164(5) Uani 1 1 d . . . . .
N3 N 0.1297(2) 0.8164(2) 0.11996(6) 0.0202(5) Uani 1 1 d . . . . .
N4 N 0.12919(19) 0.9031(2) 0.13933(6) 0.0169(4) Uani 1 1 d . . . . .
N5 N 0.1275(2) 0.9898(2) 0.15842(6) 0.0205(5) 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 O1 1.8665(18) . yes
Mn1 O2 1.8803(17) . yes
Mn1 N1 1.970(2) . yes
Mn1 N2 1.959(2) . yes
Mn1 N3 2.289(2) . yes
Mn1 N5 2.312(2) 8_655 yes
O1 C1 1.313(3) . ?
O2 C24 1.310(3) . ?
N1 C11 1.286(3) . yes
N1 C12 1.467(3) . yes
N2 C13 1.473(3) . yes
N2 C14 1.291(3) . yes
C1 C10 1.397(3) . ?
C1 C2 1.425(3) . ?
C2 C3 1.353(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(3) . ?
C4 C9 1.419(3) . ?
C5 C6 1.366(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.450(3) . ?
C10 C11 1.436(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.512(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.424(3) . ?
C14 H14 0.9500 . ?
C15 C24 1.403(3) . ?
C15 C16 1.455(3) . ?
C16 C17 1.410(4) . ?
C16 C21 1.420(3) . ?
C17 C18 1.372(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.401(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.363(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.407(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.418(4) . ?
C22 C23 1.360(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.426(3) . ?
C23 H23 0.9500 . ?
N3 N4 1.178(3) . ?
N4 N5 1.173(3) . ?
N5 Mn1 2.312(2) 8_665 ?

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 O2 95.45(8) . . yes
O1 Mn1 N2 173.29(8) . . yes
O2 Mn1 N2 91.23(8) . . yes
O1 Mn1 N1 89.64(8) . . yes
O2 Mn1 N1 174.85(8) . . yes
N2 Mn1 N1 83.69(9) . . yes
O1 Mn1 N3 89.49(8) . . yes
O2 Mn1 N3 90.85(8) . . yes
N2 Mn1 N3 91.06(9) . . yes
N1 Mn1 N3 88.38(8) . . yes
O1 Mn1 N5 92.50(8) . 8_655 yes
O2 Mn1 N5 91.41(8) . 8_655 yes
N2 Mn1 N5 86.68(9) . 8_655 yes
N1 Mn1 N5 89.17(8) . 8_655 yes
N3 Mn1 N5 176.84(8) . 8_655 yes
C1 O1 Mn1 130.46(16) . . ?
C24 O2 Mn1 129.66(16) . . ?
C11 N1 C12 122.3(2) . . ?
C11 N1 Mn1 126.83(18) . . ?
C12 N1 Mn1 110.82(15) . . ?
C14 N2 C13 120.7(2) . . ?
C14 N2 Mn1 126.31(18) . . ?
C13 N2 Mn1 112.68(15) . . ?
O1 C1 C10 124.3(2) . . ?
O1 C1 C2 115.6(2) . . ?
C10 C1 C2 120.0(2) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 C9 119.4(2) . . ?
C5 C4 C9 119.6(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 121.3(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 117.3(2) . . ?
C8 C9 C10 123.7(2) . . ?
C4 C9 C10 119.0(2) . . ?
C1 C10 C11 120.6(2) . . ?
C1 C10 C9 119.0(2) . . ?
C11 C10 C9 120.0(2) . . ?
N1 C11 C10 125.5(2) . . ?
N1 C11 H11 117.2 . . ?
C10 C11 H11 117.2 . . ?
N1 C12 C13 107.64(19) . . ?
N1 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
N1 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
N2 C13 C12 106.7(2) . . ?
N2 C13 H13A 110.4 . . ?
C12 C13 H13A 110.4 . . ?
N2 C13 H13B 110.4 . . ?
C12 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
N2 C14 C15 126.1(2) . . ?
N2 C14 H14 116.9 . . ?
C15 C14 H14 116.9 . . ?
C24 C15 C14 121.6(2) . . ?
C24 C15 C16 119.5(2) . . ?
C14 C15 C16 118.9(2) . . ?
C17 C16 C21 117.5(2) . . ?
C17 C16 C15 123.6(2) . . ?
C21 C16 C15 118.8(2) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 120.9(2) . . ?
C20 C21 C16 119.8(2) . . ?
C22 C21 C16 119.4(2) . . ?
C23 C22 C21 121.8(2) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
O2 C24 C15 124.3(2) . . ?
O2 C24 C23 115.8(2) . . ?
C15 C24 C23 119.9(2) . . ?
N4 N3 Mn1 119.05(17) . . ?
N5 N4 N3 179.3(3) . . ?
N4 N5 Mn1 120.08(18) . 8_665 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Mn1 O1 C1 -164.6(2) . . . . ?
N1 Mn1 O1 C1 16.2(2) . . . . ?
N3 Mn1 O1 C1 104.6(2) . . . . ?
N5 Mn1 O1 C1 -72.9(2) 8_655 . . . ?
O1 Mn1 O2 C24 -171.2(2) . . . . ?
N2 Mn1 O2 C24 9.5(2) . . . . ?
N3 Mn1 O2 C24 -81.6(2) . . . . ?
N5 Mn1 O2 C24 96.2(2) 8_655 . . . ?
Mn1 O1 C1 C10 -8.9(4) . . . . ?
Mn1 O1 C1 C2 172.60(16) . . . . ?
O1 C1 C2 C3 176.9(2) . . . . ?
C10 C1 C2 C3 -1.6(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -177.4(2) . . . . ?
C2 C3 C4 C9 4.0(4) . . . . ?
C3 C4 C5 C6 -177.0(2) . . . . ?
C9 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C5 C6 C7 C8 -2.3(4) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C7 C8 C9 C4 3.0(4) . . . . ?
C7 C8 C9 C10 -175.4(2) . . . . ?
C3 C4 C9 C8 174.9(2) . . . . ?
C5 C4 C9 C8 -3.7(4) . . . . ?
C3 C4 C9 C10 -6.6(4) . . . . ?
C5 C4 C9 C10 174.7(2) . . . . ?
O1 C1 C10 C11 -6.7(4) . . . . ?
C2 C1 C10 C11 171.8(2) . . . . ?
O1 C1 C10 C9 -179.6(2) . . . . ?
C2 C1 C10 C9 -1.2(4) . . . . ?
C8 C9 C10 C1 -176.4(2) . . . . ?
C4 C9 C10 C1 5.2(4) . . . . ?
C8 C9 C10 C11 10.6(4) . . . . ?
C4 C9 C10 C11 -167.7(2) . . . . ?
C12 N1 C11 C10 -172.8(2) . . . . ?
Mn1 N1 C11 C10 5.4(4) . . . . ?
C1 C10 C11 N1 8.0(4) . . . . ?
C9 C10 C11 N1 -179.2(2) . . . . ?
C11 N1 C12 C13 -142.6(2) . . . . ?
Mn1 N1 C12 C13 39.0(2) . . . . ?
C14 N2 C13 C12 -152.1(2) . . . . ?
Mn1 N2 C13 C12 33.5(2) . . . . ?
N1 C12 C13 N2 -46.1(3) . . . . ?
C13 N2 C14 C15 -176.4(2) . . . . ?
Mn1 N2 C14 C15 -2.8(4) . . . . ?
N2 C14 C15 C24 5.6(4) . . . . ?
N2 C14 C15 C16 -175.5(2) . . . . ?
C24 C15 C16 C17 178.2(2) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C24 C15 C16 C21 -1.5(4) . . . . ?
C14 C15 C16 C21 179.6(2) . . . . ?
C21 C16 C17 C18 0.2(4) . . . . ?
C15 C16 C17 C18 -179.4(3) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
C17 C18 C19 C20 1.1(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 177.6(3) . . . . ?
C19 C20 C21 C16 -1.2(4) . . . . ?
C17 C16 C21 C20 1.0(4) . . . . ?
C15 C16 C21 C20 -179.3(2) . . . . ?
C17 C16 C21 C22 -177.8(2) . . . . ?
C15 C16 C21 C22 1.9(4) . . . . ?
C20 C21 C22 C23 -179.8(3) . . . . ?
C16 C21 C22 C23 -1.0(4) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
Mn1 O2 C24 C15 -9.5(4) . . . . ?
Mn1 O2 C24 C23 171.98(17) . . . . ?
C14 C15 C24 O2 0.6(4) . . . . ?
C16 C15 C24 O2 -178.2(2) . . . . ?
C14 C15 C24 C23 179.1(2) . . . . ?
C16 C15 C24 C23 0.3(4) . . . . ?
C22 C23 C24 O2 179.2(2) . . . . ?
C22 C23 C24 C15 0.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 O2 0.95 2.58 3.361(3) 139.5 6_556
C13 H13A O1 0.99 2.25 3.231(3) 170.3 8_655
C20 H20 N3 0.95 2.57 3.514(3) 173.7 4_565

_refine_diff_density_max         0.676
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.094

