# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1042451'
_audit_update_record             
;
2015-01-07 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H19 N3'
_chemical_formula_weight         397.46

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'

_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                   15.3114(18)
_cell_length_b                   12.9392(15)
_cell_length_c                   10.8302(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.639(2)
_cell_angle_gamma                90.00
_cell_volume                     2093.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10347
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3681
_reflns_number_gt                2895
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_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)+(0.1000P)²+0.0900P] 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         3681
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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
C1 C 0.46157(10) 0.61650(11) 0.42207(13) 0.0453(4) Uani 1 1 d . . .
C2 C 0.53313(11) 0.65871(12) 0.50941(15) 0.0571(4) Uani 1 1 d . . .
H2 H 0.5918 0.6496 0.5011 0.068 Uiso 1 1 calc R . .
C3 C 0.51392(14) 0.71457(14) 0.60869(16) 0.0674(5) Uani 1 1 d . . .
H3 H 0.5607 0.7435 0.6681 0.081 Uiso 1 1 calc R . .
C4 C 0.42643(13) 0.72875(13) 0.62226(16) 0.0639(5) Uani 1 1 d . . .
H4 H 0.4156 0.7667 0.6903 0.077 Uiso 1 1 calc R . .
C5 C 0.35620(12) 0.68736(12) 0.53635(14) 0.0555(4) Uani 1 1 d . . .
H5 H 0.2978 0.6970 0.5457 0.067 Uiso 1 1 calc R . .
C6 C 0.37312(10) 0.63064(11) 0.43472(13) 0.0442(4) Uani 1 1 d . . .
C7 C 0.31561(9) 0.57533(11) 0.33175(12) 0.0418(3) Uani 1 1 d . . .
C8 C 0.37099(9) 0.52659(11) 0.26138(13) 0.0406(3) Uani 1 1 d . . .
C9 C 0.33504(9) 0.46374(11) 0.15860(13) 0.0438(4) Uani 1 1 d . . .
H9 H 0.3721 0.4304 0.1138 0.053 Uiso 1 1 calc R . .
C10 C 0.24263(9) 0.45172(11) 0.12398(13) 0.0424(3) Uani 1 1 d . . .
C11 C 0.18749(9) 0.50216(11) 0.19206(13) 0.0451(4) Uani 1 1 d . . .
H11 H 0.1258 0.4944 0.1669 0.054 Uiso 1 1 calc R . .
C12 C 0.22251(9) 0.56358(11) 0.29612(14) 0.0443(4) Uani 1 1 d . . .
C13 C 0.16259(10) 0.61657(13) 0.36736(15) 0.0533(4) Uani 1 1 d . . .
C14 C 0.14412(14) 0.72041(16) 0.3495(2) 0.0818(6) Uani 1 1 d . . .
H14 H 0.1680 0.7576 0.2913 0.098 Uiso 1 1 calc R . .
C15 C 0.0896(2) 0.7695(2) 0.4188(3) 0.1173(11) Uani 1 1 d . . .
H15 H 0.0770 0.8395 0.4063 0.141 Uiso 1 1 calc R . .
C16 C 0.05470(19) 0.7160(4) 0.5046(3) 0.1272(13) Uani 1 1 d . . .
H16 H 0.0192 0.7494 0.5516 0.153 Uiso 1 1 calc R . .
C17 C 0.07177(18) 0.6147(3) 0.5209(2) 0.1158(10) Uani 1 1 d . . .
H17 H 0.0472 0.5781 0.5789 0.139 Uiso 1 1 calc R . .
C18 C 0.12513(14) 0.56412(18) 0.45306(19) 0.0788(6) Uani 1 1 d . . .
H18 H 0.1359 0.4937 0.4655 0.095 Uiso 1 1 calc R . .
C19 C 0.20405(9) 0.38519(11) 0.01327(13) 0.0441(4) Uani 1 1 d . . .
C20 C 0.12709(10) 0.41321(13) -0.07344(14) 0.0525(4) Uani 1 1 d . . .
H20 H 0.0964 0.4726 -0.0594 0.063 Uiso 1 1 calc R . .
C21 C 0.09501(11) 0.35442(15) -0.18068(16) 0.0629(5) Uani 1 1 d . . .
H21 H 0.0436 0.3749 -0.2384 0.075 Uiso 1 1 calc R . .
C22 C 0.13921(12) 0.26540(15) -0.20191(17) 0.0681(5) Uani 1 1 d . . .
H22 H 0.1182 0.2260 -0.2741 0.082 Uiso 1 1 calc R . .
C23 C 0.21435(12) 0.23570(15) -0.11557(18) 0.0716(5) Uani 1 1 d . . .
H23 H 0.2440 0.1754 -0.1289 0.086 Uiso 1 1 calc R . .
C24 C 0.24639(11) 0.29435(13) -0.00904(16) 0.0587(4) Uani 1 1 d . . .
H24 H 0.2973 0.2727 0.0489 0.070 Uiso 1 1 calc R . .
C25 C 0.53562(9) 0.52608(12) 0.26580(14) 0.0472(4) Uani 1 1 d . . .
C26 C 0.59291(12) 0.43556(17) 0.12459(18) 0.0708(5) Uani 1 1 d . . .
H26 H 0.5853 0.3911 0.0556 0.085 Uiso 1 1 calc R . .
C27 C 0.67705(12) 0.47037(17) 0.17667(19) 0.0715(5) Uani 1 1 d . . .
H27 H 0.7268 0.4492 0.1472 0.086 Uiso 1 1 calc R . .
C28 C 0.68353(12) 0.53811(17) 0.2745(2) 0.0767(6) Uani 1 1 d . . .
H28 H 0.7396 0.5653 0.3103 0.092 Uiso 1 1 calc R . .
N1 N 0.46111(8) 0.55326(9) 0.31440(11) 0.0432(3) Uani 1 1 d . . .
N2 N 0.52124(9) 0.46239(12) 0.16802(13) 0.0604(4) Uani 1 1 d . . .
N3 N 0.61370(9) 0.56776(12) 0.32189(15) 0.0656(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
C1 C2 1.393(2) . ?
C1 C6 1.403(2) . ?
C1 N1 1.4233(18) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.4497(19) . ?
C7 C12 1.401(2) . ?
C7 C8 1.407(2) . ?
C8 C9 1.3912(19) . ?
C8 N1 1.4163(17) . ?
C9 C10 1.391(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.398(2) . ?
C10 C19 1.489(2) . ?
C11 C12 1.3873(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.489(2) . ?
C13 C18 1.373(3) . ?
C13 C14 1.378(3) . ?
C14 C15 1.391(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.358(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.340(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.385(2) . ?
C19 C24 1.389(2) . ?
C20 C21 1.385(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.322(2) . ?
C25 N3 1.3308(19) . ?
C25 N1 1.4018(19) . ?
C26 N2 1.331(2) . ?
C26 C27 1.365(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.362(3) . ?
C27 H27 0.9300 . ?
C28 N3 1.340(2) . ?
C28 H28 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
C2 C1 C6 121.02(15) . . ?
C2 C1 N1 130.09(15) . . ?
C6 C1 N1 108.86(12) . . ?
C3 C2 C1 117.68(17) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.72(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.55(17) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.28(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 119.75(14) . . ?
C5 C6 C7 132.92(15) . . ?
C1 C6 C7 107.30(13) . . ?
C12 C7 C8 119.97(13) . . ?
C12 C7 C6 132.50(14) . . ?
C8 C7 C6 107.53(12) . . ?
C9 C8 C7 121.03(13) . . ?
C9 C8 N1 130.28(13) . . ?
C7 C8 N1 108.69(12) . . ?
C10 C9 C8 118.82(13) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 120.11(13) . . ?
C9 C10 C19 118.85(13) . . ?
C11 C10 C19 121.03(12) . . ?
C12 C11 C10 121.68(13) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C7 118.36(13) . . ?
C11 C12 C13 120.81(13) . . ?
C7 C12 C13 120.83(13) . . ?
C18 C13 C14 118.27(18) . . ?
C18 C13 C12 121.24(16) . . ?
C14 C13 C12 120.48(17) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C13 C18 C17 120.6(2) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C24 117.64(14) . . ?
C20 C19 C10 121.56(13) . . ?
C24 C19 C10 120.75(13) . . ?
C19 C20 C21 121.18(15) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 120.07(16) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.32(16) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.60(17) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 121.16(15) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
N2 C25 N3 126.44(15) . . ?
N2 C25 N1 116.78(13) . . ?
N3 C25 N1 116.78(14) . . ?
N2 C26 C27 122.99(19) . . ?
N2 C26 H26 118.5 . . ?
C27 C26 H26 118.5 . . ?
C28 C27 C26 115.82(18) . . ?
C28 C27 H27 122.1 . . ?
C26 C27 H27 122.1 . . ?
N3 C28 C27 123.65(17) . . ?
N3 C28 H28 118.2 . . ?
C27 C28 H28 118.2 . . ?
C25 N1 C8 125.98(12) . . ?
C25 N1 C1 126.39(12) . . ?
C8 N1 C1 107.57(11) . . ?
C25 N2 C26 116.10(15) . . ?
C25 N3 C28 114.93(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1042452'
_audit_update_record             
;
2015-01-07 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 Mn N3 O4'
_chemical_formula_weight         375.22

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           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                   11.7689(18)
_cell_length_b                   10.7605(16)
_cell_length_c                   13.511(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.250(3)
_cell_angle_gamma                90.00
_cell_volume                     1634.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7999
_exptl_absorpt_correction_T_max  0.8508
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8088
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2870
_reflns_number_gt                2336
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_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)+(0.0800P)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         2870
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.14660(3) 0.05813(3) 0.81723(3) 0.04950(18) Uani 1 1 d . . .
O1 O 0.1920(2) -0.2012(2) 0.8977(2) 0.0955(8) Uani 1 1 d . . .
O2 O -0.0398(2) -0.0502(3) 0.6420(2) 0.1044(9) Uani 1 1 d . . .
O3 O -0.0346(2) 0.1209(3) 0.9234(2) 0.1073(9) Uani 1 1 d . . .
O4 O 0.1172(2) 0.2898(2) 0.69103(18) 0.0798(6) Uani 1 1 d . . .
C1 C 0.4898(2) 0.05007(19) 0.78860(18) 0.0446(5) Uani 1 1 d . . .
C2 C 0.6085(2) 0.0834(3) 0.8220(2) 0.0582(7) Uani 1 1 d . . .
H2 H 0.6397 0.1279 0.8831 0.070 Uiso 1 1 calc R . .
C3 C 0.6791(3) 0.0484(3) 0.7615(3) 0.0779(9) Uani 1 1 d . . .
H3 H 0.7593 0.0699 0.7821 0.094 Uiso 1 1 calc R . .
C4 C 0.6328(3) -0.0185(3) 0.6704(3) 0.0824(10) Uani 1 1 d . . .
H4 H 0.6827 -0.0424 0.6317 0.099 Uiso 1 1 calc R . .
C5 C 0.5143(3) -0.0497(2) 0.6366(2) 0.0675(8) Uani 1 1 d . . .
H5 H 0.4836 -0.0935 0.5751 0.081 Uiso 1 1 calc R . .
C6 C 0.4411(2) -0.0150(2) 0.69571(19) 0.0482(6) Uani 1 1 d . . .
C7 C 0.3146(2) -0.0296(2) 0.68106(19) 0.0491(6) Uani 1 1 d . . .
C8 C 0.2868(2) 0.0239(2) 0.76140(17) 0.0427(5) Uani 1 1 d . . .
C9 C 0.2312(3) -0.0913(3) 0.5878(2) 0.0754(9) Uani 1 1 d . . .
H9A H 0.1933 -0.1606 0.6096 0.113 Uiso 1 1 calc R . .
H9B H 0.2752 -0.1199 0.5426 0.113 Uiso 1 1 calc R . .
H9C H 0.1720 -0.0327 0.5515 0.113 Uiso 1 1 calc R . .
C10 C 0.3949(2) 0.12349(19) 0.92139(16) 0.0419(5) Uani 1 1 d . . .
C11 C 0.4858(3) 0.2094(2) 1.0772(2) 0.0603(7) Uani 1 1 d . . .
H11 H 0.5545 0.2364 1.1268 0.072 Uiso 1 1 calc R . .
C12 C 0.3799(3) 0.2220(2) 1.0981(2) 0.0653(8) Uani 1 1 d . . .
H12 H 0.3755 0.2572 1.1598 0.078 Uiso 1 1 calc R . .
C13 C 0.2809(3) 0.1807(2) 1.0246(2) 0.0616(7) Uani 1 1 d . . .
H13 H 0.2075 0.1877 1.0369 0.074 Uiso 1 1 calc R . .
C14 C 0.1300(2) 0.2048(3) 0.7428(2) 0.0560(6) Uani 1 1 d . . .
C15 C 0.0355(3) 0.0965(3) 0.8831(3) 0.0714(8) Uani 1 1 d . . .
C16 C 0.0334(3) -0.0085(3) 0.7097(2) 0.0700(8) Uani 1 1 d . . .
C17 C 0.1757(2) -0.1011(3) 0.8724(2) 0.0607(7) Uani 1 1 d . . .
N1 N 0.28555(17) 0.13032(17) 0.93485(15) 0.0469(5) Uani 1 1 d . . .
N2 N 0.49646(18) 0.16033(17) 0.98936(16) 0.0505(5) Uani 1 1 d . . .
N3 N 0.39544(16) 0.07274(15) 0.82926(14) 0.0407(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 C16 1.803(3) . ?
Mn1 C15 1.834(4) . ?
Mn1 C14 1.850(3) . ?
Mn1 C17 1.859(3) . ?
Mn1 C8 2.041(3) . ?
Mn1 N1 2.0644(19) . ?
O1 C17 1.129(3) . ?
O2 C16 1.146(3) . ?
O3 C15 1.145(4) . ?
O4 C14 1.134(3) . ?
C1 C2 1.382(4) . ?
C1 N3 1.399(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.380(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.451(4) . ?
C7 C8 1.352(3) . ?
C7 C9 1.503(4) . ?
C8 N3 1.434(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.333(3) . ?
C10 N1 1.354(3) . ?
C10 N3 1.361(3) . ?
C11 N2 1.339(3) . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(4) . ?
C12 H12 0.9300 . ?
C13 N1 1.344(3) . ?
C13 H13 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
C16 Mn1 C15 90.99(15) . . ?
C16 Mn1 C14 88.14(13) . . ?
C15 Mn1 C14 95.52(13) . . ?
C16 Mn1 C17 87.76(13) . . ?
C15 Mn1 C17 94.93(14) . . ?
C14 Mn1 C17 168.84(13) . . ?
C16 Mn1 C8 96.64(13) . . ?
C15 Mn1 C8 172.34(12) . . ?
C14 Mn1 C8 85.41(10) . . ?
C17 Mn1 C8 84.76(11) . . ?
C16 Mn1 N1 175.68(13) . . ?
C15 Mn1 N1 93.32(12) . . ?
C14 Mn1 N1 91.67(10) . . ?
C17 Mn1 N1 91.63(10) . . ?
C8 Mn1 N1 79.04(8) . . ?
C2 C1 N3 132.1(2) . . ?
C2 C1 C6 121.8(3) . . ?
N3 C1 C6 106.1(2) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 C7 132.7(3) . . ?
C1 C6 C7 107.9(2) . . ?
C8 C7 C6 109.1(2) . . ?
C8 C7 C9 127.4(3) . . ?
C6 C7 C9 123.4(3) . . ?
C7 C8 N3 106.7(2) . . ?
C7 C8 Mn1 142.08(19) . . ?
N3 C8 Mn1 111.27(16) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 N1 125.8(2) . . ?
N2 C10 N3 120.2(2) . . ?
N1 C10 N3 114.01(19) . . ?
N2 C11 C12 123.6(2) . . ?
N2 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C13 C12 C11 116.9(3) . . ?
C13 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
N1 C13 C12 122.4(3) . . ?
N1 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
O4 C14 Mn1 175.2(3) . . ?
O3 C15 Mn1 179.4(3) . . ?
O2 C16 Mn1 179.0(3) . . ?
O1 C17 Mn1 174.2(3) . . ?
C13 N1 C10 115.9(2) . . ?
C13 N1 Mn1 127.70(18) . . ?
C10 N1 Mn1 116.34(15) . . ?
C10 N2 C11 115.3(2) . . ?
C10 N3 C1 130.44(19) . . ?
C10 N3 C8 119.12(19) . . ?
C1 N3 C8 110.27(19) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.050
