# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1533551'
_audit_update_record             
;
2017-02-19 deposited with the CCDC.
2017-03-15 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 H26 Co2 N6 O11'
_chemical_formula_weight         740.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   22.089(13)
_cell_length_b                   6.142(4)
_cell_length_c                   13.906(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.968(9)
_cell_angle_gamma                90.00
_cell_volume                     1527.0(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    756
_cell_measurement_theta_min      0.872
_cell_measurement_theta_max      0.893

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    1.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.893
_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  'Brucker SMART APEX'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5487
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2954
_reflns_number_gt                2541
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.95(4)
_refine_ls_number_reflns         2954
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.197
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.004

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
Co1 Co 0.08289(4) 0.25365(14) 0.20097(7) 0.0232(2) Uani 1 1 d . . .
N3 N 0.2285(4) 0.260(2) 0.5828(6) 0.067(2) Uani 1 1 d . . .
H3B H 0.2396 0.2532 0.6532 0.081 Uiso 1 1 calc R . .
N1 N 0.0041(3) 0.3287(9) 0.2407(5) 0.0236(12) Uani 1 1 d . . .
H1A H 0.0141 0.4637 0.2737 0.028 Uiso 1 1 calc R . .
O1W O 0.0000 0.1545(11) 0.0000 0.0244(13) Uani 1 2 d S . .
C7 C -0.2514(3) 0.2507(19) 0.1122(6) 0.0333(13) Uani 1 1 d . . .
H7A H -0.2881 0.1450 0.0852 0.040 Uiso 1 1 calc R . .
C10 C 0.0842(3) 0.2497(19) 0.4575(5) 0.0342(14) Uani 1 1 d . . .
H10A H 0.0709 0.3937 0.4681 0.041 Uiso 1 1 calc R . .
H10B H 0.0885 0.1548 0.5169 0.041 Uiso 1 1 calc R . .
N2 N 0.1652(3) 0.2769(12) 0.3845(5) 0.0309(13) Uani 1 1 d . . .
C11 C 0.1574(4) 0.2614(16) 0.4770(5) 0.0348(14) Uani 1 1 d . . .
O1 O -0.3877(3) 0.3919(9) 0.0563(5) 0.0360(12) Uani 1 1 d . . .
O3 O 0.0568(3) -0.0542(8) 0.2307(4) 0.0306(11) Uani 1 1 d . . .
C8 C -0.0734(4) 0.3209(14) 0.1353(6) 0.036(2) Uani 1 1 d . . .
H8A H -0.0820 0.1781 0.0996 0.043 Uiso 1 1 calc R . .
H8B H -0.0788 0.4264 0.0788 0.043 Uiso 1 1 calc R . .
C2 C -0.2595(4) 0.4533(13) 0.1480(6) 0.0281(14) Uani 1 1 d . . .
C5 C -0.1347(4) 0.3631(13) 0.1508(6) 0.0327(16) Uani 1 1 d . . .
O2W O 0.0751(3) 0.5703(9) 0.1494(5) 0.0430(13) Uani 1 1 d . . .
C14 C 0.0412(4) -0.0528(12) 0.3045(6) 0.0283(15) Uani 1 1 d . . .
C1 C -0.3317(4) 0.5103(12) 0.1282(6) 0.0276(14) Uani 1 1 d . . .
O4 O 0.0451(3) -0.2174(10) 0.3588(5) 0.0482(15) Uani 1 1 d . . .
C12 C 0.2774(3) 0.2727(15) 0.5538(6) 0.0347(16) Uani 1 1 d . . .
H12A H 0.3292 0.2745 0.6075 0.042 Uiso 1 1 calc R . .
C13 C 0.2387(4) 0.2818(14) 0.4353(6) 0.0374(17) Uani 1 1 d . . .
H13A H 0.2600 0.2904 0.3942 0.045 Uiso 1 1 calc R . .
C3 C -0.2021(4) 0.6052(13) 0.1934(7) 0.0372(17) Uani 1 1 d . . .
H3A H -0.2050 0.7374 0.2231 0.045 Uiso 1 1 calc R . .
C6 C -0.1885(4) 0.2076(13) 0.1169(6) 0.040(2) Uani 1 1 d . . .
H6A H -0.1822 0.0694 0.0966 0.048 Uiso 1 1 calc R . .
C4 C -0.1404(4) 0.5577(14) 0.1941(7) 0.0390(18) Uani 1 1 d . . .
H4A H -0.1021 0.6594 0.2245 0.047 Uiso 1 1 calc R . .
O2 O -0.3338(3) 0.6735(9) 0.1807(4) 0.0351(12) Uani 1 1 d . . .
C9 C 0.0199(4) 0.1632(12) 0.3307(6) 0.0271(14) Uani 1 1 d . . .
H9A H -0.0252 0.1419 0.3275 0.033 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2W 2.045(5) . ?
Co1 O2 2.079(5) 3_545 ?
Co1 O3 2.087(5) . ?
Co1 N2 2.095(5) . ?
Co1 N1 2.162(5) . ?
Co1 O1W 2.350(2) . ?
N3 C12 1.358(11) . ?
N3 C11 1.385(9) . ?
N1 C8 1.460(9) . ?
N1 C9 1.486(9) . ?
O1W Co1 2.350(2) 2 ?
C7 C6 1.377(9) . ?
C7 C2 1.391(14) . ?
C10 C11 1.474(9) . ?
C10 C9 1.570(9) . ?
N2 C13 1.338(8) . ?
N2 C11 1.398(8) . ?
O1 C1 1.267(9) . ?
O3 C14 1.260(8) . ?
C8 C5 1.514(9) . ?
C2 C3 1.392(10) . ?
C2 C1 1.493(9) . ?
C5 C6 1.374(11) . ?
C5 C4 1.377(11) . ?
C14 O4 1.234(10) . ?
C14 C9 1.521(10) . ?
C1 O2 1.256(9) . ?
C12 C13 1.339(10) . ?
C3 C4 1.388(11) . ?
O2 Co1 2.079(5) 3_455 ?

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
O2W Co1 O2 94.4(2) . 3_545 ?
O2W Co1 O3 162.7(2) . . ?
O2 Co1 O3 100.5(2) 3_545 . ?
O2W Co1 N2 101.3(3) . . ?
O2 Co1 N2 88.7(2) 3_545 . ?
O3 Co1 N2 87.9(2) . . ?
O2W Co1 N1 88.4(2) . . ?
O2 Co1 N1 174.3(2) 3_545 . ?
O3 Co1 N1 77.6(2) . . ?
N2 Co1 N1 85.8(2) . . ?
O2W Co1 O1W 89.0(2) . . ?
O2 Co1 O1W 84.88(14) 3_545 . ?
O3 Co1 O1W 83.6(2) . . ?
N2 Co1 O1W 168.2(2) . . ?
N1 Co1 O1W 100.20(16) . . ?
C12 N3 C11 106.8(6) . . ?
C8 N1 C9 112.4(5) . . ?
C8 N1 Co1 112.4(4) . . ?
C9 N1 Co1 104.0(4) . . ?
Co1 O1W Co1 149.9(3) . 2 ?
C6 C7 C2 119.6(8) . . ?
C11 C10 C9 113.2(5) . . ?
C13 N2 C11 106.5(5) . . ?
C13 N2 Co1 124.1(5) . . ?
C11 N2 Co1 128.9(4) . . ?
N3 C11 N2 107.5(6) . . ?
N3 C11 C10 129.2(6) . . ?
N2 C11 C10 123.2(5) . . ?
C14 O3 Co1 113.2(4) . . ?
N1 C8 C5 118.1(6) . . ?
C3 C2 C7 119.2(6) . . ?
C3 C2 C1 121.1(7) . . ?
C7 C2 C1 119.5(6) . . ?
C6 C5 C4 118.1(6) . . ?
C6 C5 C8 119.9(7) . . ?
C4 C5 C8 122.0(7) . . ?
O4 C14 O3 122.6(7) . . ?
O4 C14 C9 119.2(6) . . ?
O3 C14 C9 118.2(6) . . ?
O2 C1 O1 124.4(6) . . ?
O2 C1 C2 118.6(6) . . ?
O1 C1 C2 116.9(6) . . ?
C13 C12 N3 108.9(6) . . ?
N2 C13 C12 110.4(7) . . ?
C4 C3 C2 119.4(7) . . ?
C5 C6 C7 121.8(8) . . ?
C5 C4 C3 121.4(7) . . ?
C1 O2 Co1 127.2(4) . 3_455 ?
N1 C9 C14 110.3(5) . . ?
N1 C9 C10 108.9(6) . . ?
C14 C9 C10 111.2(6) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.314
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.131
####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1533552'
_audit_update_record             
;
2017-02-19 deposited with the CCDC.
2017-03-15 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 H24 Mn2 N6 O11'
_chemical_formula_weight         730.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   22.4588(11)
_cell_length_b                   6.1786(4)
_cell_length_c                   14.1282(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.551(4)
_cell_angle_gamma                90.00
_cell_volume                     1554.29(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    744
_cell_measurement_theta_min      0.433
_cell_measurement_theta_max      0.494

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    0.882
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.433
_exptl_absorpt_correction_T_max  0.494
_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  'Brucker SMART APEX'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1275
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.95
_diffrn_reflns_theta_max         50.96
_reflns_number_total             1275
_reflns_number_gt                1232
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.1546P)²+3.5451P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(11)
_refine_ls_number_reflns         1275
_refine_ls_number_parameters     213
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1806
_refine_ls_wR_factor_gt          0.1769
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.090
_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 0.41695(6) 0.6089(2) 0.30165(10) 0.0144(6) Uani 1 1 d . . .
C12 C 0.2665(5) 0.621(2) -0.0914(8) 0.025(2) Uani 1 1 d . . .
H12A H 0.2547 0.6300 -0.1669 0.030 Uiso 1 1 calc R . .
N2 N 0.3290(4) 0.6017(17) 0.1053(6) 0.0185(18) Uani 1 1 d . . .
O1W O 0.5000 0.7253(18) 0.5000 0.018(2) Uani 1 2 d S . .
N3 N 0.2171(4) 0.6100(17) -0.0658(6) 0.028(2) Uani 1 1 d . . .
H3B H 0.1689 0.6087 -0.1169 0.033 Uiso 1 1 calc R . .
O4 O 0.4538(3) 1.0786(12) 0.1355(5) 0.0252(18) Uani 1 1 d . . .
C10 C 0.4109(5) 0.617(2) 0.0360(7) 0.018(2) Uani 1 1 d . . .
H10A H 0.4068 0.7096 -0.0232 0.022 Uiso 1 1 calc R . .
H10B H 0.4217 0.4716 0.0245 0.022 Uiso 1 1 calc R . .
C7 C 0.7509(5) 0.610(2) 0.3877(7) 0.022(2) Uani 1 1 d . . .
H7A H 0.7877 0.7148 0.4146 0.026 Uiso 1 1 calc R . .
N1 N 0.4957(4) 0.5338(13) 0.2525(6) 0.0162(19) Uani 1 1 d U . .
H1A H 0.4858 0.3988 0.2204 0.019 Uiso 1 1 calc R . .
O3 O 0.4498(3) 0.9209(10) 0.2699(5) 0.0190(16) Uani 1 1 d . . .
O2 O 0.8854(3) 0.4692(12) 0.4394(5) 0.0191(16) Uani 1 1 d . . .
O1 O 0.8295(3) 0.1887(12) 0.3177(6) 0.0258(19) Uani 1 1 d . . .
O2W O 0.4271(4) 0.2757(12) 0.3506(6) 0.0233(17) Uani 1 1 d . . .
C13 C 0.2565(5) 0.6019(19) 0.0522(8) 0.022(2) Uani 1 1 d . . .
H13A H 0.2355 0.5970 0.0921 0.026 Uiso 1 1 calc R . .
C14 C 0.4599(5) 0.9147(17) 0.1913(8) 0.013(2) Uani 1 1 d U . .
C11 C 0.3366(5) 0.6160(18) 0.0151(8) 0.019(2) Uani 1 1 d . . .
C8 C 0.5746(5) 0.5454(19) 0.3595(8) 0.024(3) Uani 1 1 d . . .
H8A H 0.5866 0.5809 0.4333 0.028 Uiso 1 1 calc R . .
C5 C 0.6346(6) 0.4998(18) 0.3481(8) 0.024(3) Uani 1 1 d . . .
C9 C 0.4771(5) 0.6960(17) 0.1613(8) 0.020(2) Uani 1 1 d . . .
H9A H 0.5210 0.7142 0.1627 0.023 Uiso 1 1 calc R . .
C4 C 0.6395(5) 0.3034(18) 0.3015(8) 0.021(3) Uani 1 1 d . . .
H4A H 0.6011 0.2023 0.2698 0.025 Uiso 1 1 calc R . .
C6 C 0.6891(5) 0.6537(18) 0.3846(8) 0.022(3) Uani 1 1 d . . .
H6A H 0.6844 0.7897 0.4075 0.027 Uiso 1 1 calc R . .
C2 C 0.7575(5) 0.4092(19) 0.3506(8) 0.019(2) Uani 1 1 d . . .
C1 C 0.8297(5) 0.3588(18) 0.3699(8) 0.017(2) Uani 1 1 d . . .
C3 C 0.6990(5) 0.2588(19) 0.3021(7) 0.022(3) Uani 1 1 d . . .
H3A H 0.7009 0.1293 0.2704 0.027 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O2W 2.139(7) . ?
Mn1 O1 2.166(7) 3_455 ?
Mn1 O3 2.206(6) . ?
Mn1 N2 2.218(6) . ?
Mn1 N1 2.308(7) . ?
Mn1 O1W 2.341(4) . ?
C12 N3 1.362(12) . ?
C12 C11 1.363(13) . ?
C12 H12A 0.9300 . ?
N2 C13 1.313(12) . ?
N2 C11 1.386(11) . ?
O1W Mn1 2.341(4) 2_656 ?
N3 C13 1.329(12) . ?
N3 H3B 0.8600 . ?
O4 C14 1.239(13) . ?
C10 C11 1.508(13) . ?
C10 C9 1.541(13) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 C6 1.387(13) . ?
C7 C2 1.390(17) . ?
C7 H7A 0.9300 . ?
N1 C8 1.471(12) . ?
N1 C9 1.478(12) . ?
N1 H1A 0.9100 . ?
O3 C14 1.261(11) . ?
O2 C1 1.223(12) . ?
O1 C1 1.283(12) . ?
O1 Mn1 2.166(7) 3_545 ?
C13 H13A 0.9300 . ?
C14 C9 1.535(15) . ?
C8 C5 1.478(14) . ?
C8 H8A 0.9300 . ?
C5 C6 1.379(15) . ?
C5 C4 1.417(16) . ?
C9 H9A 0.9800 . ?
C4 C3 1.360(14) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C2 C3 1.400(15) . ?
C2 C1 1.505(13) . ?
C3 H3A 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
O2W Mn1 O1 96.3(3) . 3_455 ?
O2W Mn1 O3 157.5(2) . . ?
O1 Mn1 O3 105.0(3) 3_455 . ?
O2W Mn1 N2 102.9(3) . . ?
O1 Mn1 N2 87.9(2) 3_455 . ?
O3 Mn1 N2 85.2(3) . . ?
O2W Mn1 N1 87.4(3) . . ?
O1 Mn1 N1 170.9(2) 3_455 . ?
O3 Mn1 N1 72.6(3) . . ?
N2 Mn1 N1 83.2(3) . . ?
O2W Mn1 O1W 93.4(3) . . ?
O1 Mn1 O1W 85.21(18) 3_455 . ?
O3 Mn1 O1W 81.6(3) . . ?
N2 Mn1 O1W 162.9(3) . . ?
N1 Mn1 O1W 102.96(19) . . ?
N3 C12 C11 106.6(7) . . ?
N3 C12 H12A 126.7 . . ?
C11 C12 H12A 126.7 . . ?
C13 N2 C11 106.2(7) . . ?
C13 N2 Mn1 124.3(6) . . ?
C11 N2 Mn1 129.3(6) . . ?
Mn1 O1W Mn1 144.2(5) . 2_656 ?
C13 N3 C12 107.9(7) . . ?
C13 N3 H3B 126.1 . . ?
C12 N3 H3B 126.1 . . ?
C11 C10 C9 113.9(7) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C6 C7 C2 119.7(10) . . ?
C6 C7 H7A 120.1 . . ?
C2 C7 H7A 120.1 . . ?
C8 N1 C9 112.7(7) . . ?
C8 N1 Mn1 110.2(5) . . ?
C9 N1 Mn1 105.4(5) . . ?
C8 N1 H1A 109.5 . . ?
C9 N1 H1A 109.5 . . ?
Mn1 N1 H1A 109.5 . . ?
C14 O3 Mn1 114.5(6) . . ?
C1 O1 Mn1 124.1(6) . 3_545 ?
N2 C13 N3 111.3(8) . . ?
N2 C13 H13A 124.4 . . ?
N3 C13 H13A 124.4 . . ?
O4 C14 O3 121.8(9) . . ?
O4 C14 C9 119.5(7) . . ?
O3 C14 C9 118.7(8) . . ?
C12 C11 N2 108.1(7) . . ?
C12 C11 C10 127.7(8) . . ?
N2 C11 C10 124.2(7) . . ?
N1 C8 C5 119.0(7) . . ?
N1 C8 H8A 120.5 . . ?
C5 C8 H8A 120.5 . . ?
C6 C5 C4 117.5(9) . . ?
C6 C5 C8 119.3(10) . . ?
C4 C5 C8 123.3(10) . . ?
N1 C9 C14 109.9(7) . . ?
N1 C9 C10 110.4(8) . . ?
C14 C9 C10 111.5(8) . . ?
N1 C9 H9A 108.3 . . ?
C14 C9 H9A 108.3 . . ?
C10 C9 H9A 108.3 . . ?
C3 C4 C5 121.7(10) . . ?
C3 C4 H4A 119.1 . . ?
C5 C4 H4A 119.1 . . ?
C5 C6 C7 121.4(11) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C7 C2 C3 119.6(9) . . ?
C7 C2 C1 117.9(9) . . ?
C3 C2 C1 122.5(10) . . ?
O2 C1 O1 124.2(9) . . ?
O2 C1 C2 119.5(9) . . ?
O1 C1 C2 116.1(9) . . ?
C4 C3 C2 119.6(11) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2W Mn1 N2 C13 83.6(10) . . . . ?
O1 Mn1 N2 C13 -12.4(10) 3_455 . . . ?
O3 Mn1 N2 C13 -117.7(10) . . . . ?
N1 Mn1 N2 C13 169.3(10) . . . . ?
O1W Mn1 N2 C13 -78.4(13) . . . . ?
O2W Mn1 N2 C11 -102.9(10) . . . . ?
O1 Mn1 N2 C11 161.1(10) 3_455 . . . ?
O3 Mn1 N2 C11 55.8(10) . . . . ?
N1 Mn1 N2 C11 -17.2(10) . . . . ?
O1W Mn1 N2 C11 95.1(11) . . . . ?
O2W Mn1 O1W Mn1 6.24(17) . . . 2_656 ?
O1 Mn1 O1W Mn1 102.3(2) 3_455 . . 2_656 ?
O3 Mn1 O1W Mn1 -151.69(17) . . . 2_656 ?
N2 Mn1 O1W Mn1 168.7(7) . . . 2_656 ?
N1 Mn1 O1W Mn1 -81.8(2) . . . 2_656 ?
C11 C12 N3 C13 0.8(15) . . . . ?
O2W Mn1 N1 C8 -84.3(6) . . . . ?
O1 Mn1 N1 C8 161.7(17) 3_455 . . . ?
O3 Mn1 N1 C8 85.3(6) . . . . ?
N2 Mn1 N1 C8 172.4(7) . . . . ?
O1W Mn1 N1 C8 8.6(7) . . . . ?
O2W Mn1 N1 C9 153.9(6) . . . . ?
O1 Mn1 N1 C9 40(2) 3_455 . . . ?
O3 Mn1 N1 C9 -36.6(5) . . . . ?
N2 Mn1 N1 C9 50.5(6) . . . . ?
O1W Mn1 N1 C9 -113.3(6) . . . . ?
O2W Mn1 O3 C14 61.2(9) . . . . ?
O1 Mn1 O3 C14 -137.8(6) 3_455 . . . ?
N2 Mn1 O3 C14 -51.3(6) . . . . ?
N1 Mn1 O3 C14 33.0(6) . . . . ?
O1W Mn1 O3 C14 139.5(6) . . . . ?
C11 N2 C13 N3 1.5(14) . . . . ?
Mn1 N2 C13 N3 176.3(7) . . . . ?
C12 N3 C13 N2 -1.5(15) . . . . ?
Mn1 O3 C14 O4 155.7(7) . . . . ?
Mn1 O3 C14 C9 -22.0(9) . . . . ?
N3 C12 C11 N2 0.1(15) . . . . ?
N3 C12 C11 C10 178.0(12) . . . . ?
C13 N2 C11 C12 -1.0(14) . . . . ?
Mn1 N2 C11 C12 -175.4(9) . . . . ?
C13 N2 C11 C10 -178.9(11) . . . . ?
Mn1 N2 C11 C10 6.7(17) . . . . ?
C9 C10 C11 C12 158.1(12) . . . . ?
C9 C10 C11 N2 -24.4(16) . . . . ?
C9 N1 C8 C5 -63.4(12) . . . . ?
Mn1 N1 C8 C5 179.2(8) . . . . ?
N1 C8 C5 C6 123.4(10) . . . . ?
N1 C8 C5 C4 -56.9(13) . . . . ?
C8 N1 C9 C14 -82.7(9) . . . . ?
Mn1 N1 C9 C14 37.5(8) . . . . ?
C8 N1 C9 C10 153.8(8) . . . . ?
Mn1 N1 C9 C10 -86.0(7) . . . . ?
O4 C14 C9 N1 169.5(7) . . . . ?
O3 C14 C9 N1 -12.8(11) . . . . ?
O4 C14 C9 C10 -67.7(10) . . . . ?
O3 C14 C9 C10 110.0(9) . . . . ?
C11 C10 C9 N1 70.7(11) . . . . ?
C11 C10 C9 C14 -51.8(12) . . . . ?
C6 C5 C4 C3 5.7(13) . . . . ?
C8 C5 C4 C3 -174.1(9) . . . . ?
C4 C5 C6 C7 -6.8(13) . . . . ?
C8 C5 C6 C7 173.0(8) . . . . ?
C2 C7 C6 C5 1.7(13) . . . . ?
C6 C7 C2 C3 4.8(13) . . . . ?
C6 C7 C2 C1 -172.5(8) . . . . ?
Mn1 O1 C1 O2 -17.5(12) 3_545 . . . ?
Mn1 O1 C1 C2 168.1(6) 3_545 . . . ?
C7 C2 C1 O2 16.3(13) . . . . ?
C3 C2 C1 O2 -160.9(9) . . . . ?
C7 C2 C1 O1 -169.0(8) . . . . ?
C3 C2 C1 O1 13.8(12) . . . . ?
C5 C4 C3 C2 0.6(13) . . . . ?
C7 C2 C3 C4 -5.9(13) . . . . ?
C1 C2 C3 C4 171.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        50.96
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.126
