# 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 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_268
_database_code_depnum_ccdc_archive 'CCDC 1037113'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 Co N5 O4'
_chemical_formula_weight         476.35

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   P21/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                   10.225(5)
_cell_length_b                   13.530(6)
_cell_length_c                   15.503(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.795(9)
_cell_angle_gamma                90.00
_cell_volume                     2091.6(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       acicular
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_T_max  0.8817
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'rigaku MM007 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17615
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4753
_reflns_number_gt                3604
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0412P)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         4753
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.73949(3) 0.69145(3) 0.96927(3) 0.03364(14) Uani 1 1 d . . .
O1 O 0.58853(18) 0.78674(16) 0.96258(15) 0.0443(6) Uani 1 1 d . . .
O2 O 0.49563(19) 0.64704(17) 0.99273(16) 0.0464(6) Uani 1 1 d . . .
O3 O -0.00582(19) 0.64020(17) 0.95733(16) 0.0515(6) Uani 1 1 d . . .
O4 O -0.11657(17) 0.78143(15) 0.94852(14) 0.0380(5) Uani 1 1 d . . .
N1 N 0.2326(2) 1.0481(2) 0.9628(2) 0.0592(9) Uani 1 1 d . . .
H1A H 0.1576 1.0789 0.9571 0.071 Uiso 1 1 calc R . .
H1B H 0.3057 1.0809 0.9664 0.071 Uiso 1 1 calc R . .
N2 N 0.6942(2) 0.58652(19) 0.87622(16) 0.0357(6) Uani 1 1 d . . .
N3 N 0.6243(2) 0.4492(2) 0.80622(19) 0.0491(7) Uani 1 1 d . . .
N4 N 0.8878(2) -0.0447(2) 0.70658(19) 0.0459(7) Uani 1 1 d . . .
N5 N 0.8000(2) -0.1381(2) 0.59285(17) 0.0381(6) Uani 1 1 d . . .
C1 C -0.0079(3) 0.7309(2) 0.9542(2) 0.0358(7) Uani 1 1 d . . .
C2 C 0.1194(2) 0.7884(2) 0.95839(19) 0.0326(7) Uani 1 1 d . . .
C3 C 0.1189(3) 0.8901(2) 0.9603(2) 0.0368(7) Uani 1 1 d . . .
H3 H 0.0383 0.9231 0.9576 0.044 Uiso 1 1 calc R . .
C4 C 0.2357(3) 0.9448(2) 0.9660(2) 0.0411(8) Uani 1 1 d . . .
C5 C 0.3553(3) 0.8934(2) 0.9701(2) 0.0389(7) Uani 1 1 d . . .
H5 H 0.4346 0.9283 0.9733 0.047 Uiso 1 1 calc R . .
C6 C 0.3577(3) 0.7907(2) 0.9695(2) 0.0346(7) Uani 1 1 d . . .
C7 C 0.2393(2) 0.7384(2) 0.9638(2) 0.0371(7) Uani 1 1 d . . .
H7 H 0.2405 0.6696 0.9636 0.044 Uiso 1 1 calc R . .
C8 C 0.4879(3) 0.7362(2) 0.9764(2) 0.0355(7) Uani 1 1 d . . .
C9 C 0.6320(3) 0.5020(2) 0.8800(2) 0.0379(7) Uani 1 1 d . . .
H9 H 0.5977 0.4817 0.9278 0.045 Uiso 1 1 calc R . .
C10 C 0.7294(3) 0.5876(3) 0.7955(2) 0.0472(8) Uani 1 1 d . . .
H10 H 0.7759 0.6381 0.7746 0.057 Uiso 1 1 calc R . .
C11 C 0.6854(3) 0.5035(3) 0.7514(2) 0.0601(11) Uani 1 1 d . . .
H11 H 0.6947 0.4860 0.6950 0.072 Uiso 1 1 calc R . .
C12 C 0.5673(3) 0.3503(3) 0.7889(3) 0.0660(12) Uani 1 1 d . . .
H12A H 0.4993 0.3518 0.7343 0.079 Uiso 1 1 calc R . .
H12B H 0.5235 0.3325 0.8362 0.079 Uiso 1 1 calc R . .
C13 C 0.6682(3) 0.2719(3) 0.7818(2) 0.0487(9) Uani 1 1 d . . .
C14 C 0.8050(3) 0.2810(3) 0.8176(3) 0.0657(12) Uani 1 1 d . . .
H14 H 0.8382 0.3384 0.8476 0.079 Uiso 1 1 calc R . .
C15 C 0.8911(3) 0.2059(3) 0.8088(3) 0.0591(10) Uani 1 1 d . . .
H15 H 0.9822 0.2135 0.8329 0.071 Uiso 1 1 calc R . .
C16 C 0.8466(3) 0.1198(3) 0.7657(2) 0.0429(8) Uani 1 1 d . . .
C17 C 0.7107(3) 0.1108(3) 0.7316(2) 0.0603(10) Uani 1 1 d . . .
H17 H 0.6775 0.0531 0.7020 0.072 Uiso 1 1 calc R . .
C18 C 0.6235(3) 0.1853(3) 0.7403(2) 0.0553(10) Uani 1 1 d . . .
H18 H 0.5322 0.1767 0.7175 0.066 Uiso 1 1 calc R . .
C19 C 0.9473(3) 0.0424(3) 0.7544(3) 0.0625(11) Uani 1 1 d . . .
H19A H 1.0101 0.0714 0.7230 0.075 Uiso 1 1 calc R . .
H19B H 0.9976 0.0223 0.8124 0.075 Uiso 1 1 calc R . .
C20 C 0.8710(3) -0.0578(2) 0.6191(2) 0.0423(8) Uani 1 1 d . . .
H20 H 0.9050 -0.0159 0.5819 0.051 Uiso 1 1 calc R . .
C21 C 0.7702(3) -0.1776(3) 0.6675(2) 0.0458(8) Uani 1 1 d . . .
H21 H 0.7205 -0.2348 0.6693 0.055 Uiso 1 1 calc R . .
C22 C 0.8239(3) -0.1209(3) 0.7384(2) 0.0522(9) Uani 1 1 d . . .
H22 H 0.8185 -0.1315 0.7968 0.063 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 O4 1.990(2) 1_655 ?
Co1 O1 1.996(2) . ?
Co1 N2 2.004(3) . ?
Co1 N5 2.013(3) 4_566 ?
O1 C8 1.292(3) . ?
O2 C8 1.232(4) . ?
O3 C1 1.228(4) . ?
O4 C1 1.291(3) . ?
O4 Co1 1.9905(19) 1_455 ?
N1 C4 1.399(4) . ?
N2 C9 1.316(4) . ?
N2 C10 1.377(4) . ?
N3 C9 1.336(4) . ?
N3 C11 1.374(4) . ?
N3 C12 1.460(4) . ?
N4 C20 1.340(4) . ?
N4 C22 1.370(4) . ?
N4 C19 1.452(4) . ?
N5 C20 1.319(4) . ?
N5 C21 1.370(4) . ?
N5 Co1 2.013(3) 4_565 ?
C1 C2 1.505(4) . ?
C2 C3 1.376(4) . ?
C2 C7 1.387(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.397(4) . ?
C5 C6 1.390(4) . ?
C6 C7 1.388(4) . ?
C6 C8 1.504(4) . ?
C10 C11 1.352(5) . ?
C12 C13 1.501(5) . ?
C13 C18 1.365(5) . ?
C13 C14 1.391(5) . ?
C14 C15 1.371(5) . ?
C15 C16 1.370(5) . ?
C16 C17 1.378(4) . ?
C16 C19 1.506(5) . ?
C17 C18 1.372(5) . ?
C21 C22 1.352(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Co1 O1 100.81(9) 1_655 . ?
O4 Co1 N2 112.22(9) 1_655 . ?
O1 Co1 N2 111.57(9) . . ?
O4 Co1 N5 106.91(9) 1_655 4_566 ?
O1 Co1 N5 110.64(10) . 4_566 ?
N2 Co1 N5 113.85(11) . 4_566 ?
C8 O1 Co1 106.54(19) . . ?
C1 O4 Co1 108.70(19) . 1_455 ?
C9 N2 C10 106.0(3) . . ?
C9 N2 Co1 128.4(2) . . ?
C10 N2 Co1 125.6(2) . . ?
C9 N3 C11 107.1(3) . . ?
C9 N3 C12 126.3(3) . . ?
C11 N3 C12 126.5(3) . . ?
C20 N4 C22 107.5(3) . . ?
C20 N4 C19 124.7(3) . . ?
C22 N4 C19 127.4(3) . . ?
C20 N5 C21 105.7(3) . . ?
C20 N5 Co1 128.4(2) . 4_565 ?
C21 N5 Co1 125.8(2) . 4_565 ?
O3 C1 O4 122.6(2) . . ?
O3 C1 C2 120.5(2) . . ?
O4 C1 C2 116.8(3) . . ?
C3 C2 C7 119.6(2) . . ?
C3 C2 C1 120.7(2) . . ?
C7 C2 C1 119.7(3) . . ?
C2 C3 C4 121.8(3) . . ?
C3 C4 C5 117.9(3) . . ?
C3 C4 N1 121.2(3) . . ?
C5 C4 N1 120.8(3) . . ?
C6 C5 C4 120.9(3) . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 C8 120.0(3) . . ?
C5 C6 C8 120.4(2) . . ?
C2 C7 C6 120.2(3) . . ?
O2 C8 O1 122.3(2) . . ?
O2 C8 C6 120.7(2) . . ?
O1 C8 C6 117.0(3) . . ?
N2 C9 N3 111.4(3) . . ?
C11 C10 N2 109.0(3) . . ?
C10 C11 N3 106.5(3) . . ?
N3 C12 C13 114.1(3) . . ?
C18 C13 C14 117.8(3) . . ?
C18 C13 C12 118.5(3) . . ?
C14 C13 C12 123.7(3) . . ?
C15 C14 C13 120.4(3) . . ?
C16 C15 C14 121.9(3) . . ?
C15 C16 C17 117.4(3) . . ?
C15 C16 C19 119.1(3) . . ?
C17 C16 C19 123.5(3) . . ?
C18 C17 C16 121.3(3) . . ?
C13 C18 C17 121.3(3) . . ?
N4 C19 C16 113.8(3) . . ?
N5 C20 N4 111.1(3) . . ?
C22 C21 N5 109.8(3) . . ?
C21 C22 N4 106.0(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
N1 H1A O4 0.86 2.48 3.056(3) 124.9 3_577
N1 H1B O1 0.86 2.25 2.956(3) 139.4 3_677

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_285
_database_code_depnum_ccdc_archive 'CCDC 1037114'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Co N3 O5'
_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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.630(4)
_cell_length_b                   10.167(5)
_cell_length_c                   12.475(7)
_cell_angle_alpha                109.11(3)
_cell_angle_beta                 103.70(2)
_cell_angle_gamma                100.43(3)
_cell_volume                     740.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    1.191
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_T_max  0.8702
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'rigaku MM007 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5814
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3361
_reflns_number_gt                2815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0441P)²+0.0537P] 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         3361
_refine_ls_number_parameters     225
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.53487(5) 0.64204(3) 0.83564(3) 0.01960(11) Uani 1 1 d . . .
O1 O 0.8166(2) 0.54523(17) 0.82083(14) 0.0231(3) Uani 1 1 d . . .
O2 O 0.5247(2) 0.43704(17) 0.84727(14) 0.0230(3) Uani 1 1 d . . .
O3 O 0.3978(3) -0.0550(2) 0.84079(18) 0.0373(4) Uani 1 1 d . . .
O4 O 0.6563(3) -0.16803(17) 0.82418(15) 0.0269(4) Uani 1 1 d . . .
N1 N 0.3693(3) 0.5337(2) 0.65275(16) 0.0246(4) Uani 1 1 d . . .
N2 N 0.1795(3) 0.3556(2) 0.47924(17) 0.0265(4) Uani 1 1 d . . .
N3 N 1.3287(3) 0.2574(2) 0.96818(15) 0.0201(4) Uani 1 1 d . . .
H3A H 1.4003 0.3142 0.9390 0.024 Uiso 1 1 calc R . .
H3B H 1.3598 0.1720 0.9441 0.024 Uiso 1 1 calc R . .
C1 C 0.7106(3) 0.4399(2) 0.83515(18) 0.0181(4) Uani 1 1 d . . .
C2 C 0.7997(4) 0.3168(2) 0.84356(18) 0.0182(4) Uani 1 1 d . . .
C3 C 0.6580(3) 0.1851(2) 0.82202(18) 0.0190(4) Uani 1 1 d . . .
H3 H 0.5097 0.1697 0.7910 0.023 Uiso 1 1 calc R . .
C4 C 0.7361(3) 0.0768(2) 0.84637(18) 0.0184(4) Uani 1 1 d . . .
C5 C 0.5819(4) -0.0587(2) 0.83578(19) 0.0209(5) Uani 1 1 d . . .
C6 C 0.9589(4) 0.0999(2) 0.89071(18) 0.0197(4) Uani 1 1 d . . .
H6 H 1.0121 0.0272 0.9063 0.024 Uiso 1 1 calc R . .
C7 C 1.1017(3) 0.2304(2) 0.91170(18) 0.0174(4) Uani 1 1 d . . .
C8 C 1.0232(4) 0.3395(2) 0.88729(18) 0.0203(5) Uani 1 1 d . . .
H8 H 1.1186 0.4264 0.9000 0.024 Uiso 1 1 calc R . .
C9 C 0.2753(4) 0.3933(3) 0.5974(2) 0.0273(5) Uani 1 1 d . . .
H9 H 0.2750 0.3280 0.6350 0.033 Uiso 1 1 calc R . .
C10 C 0.3325(4) 0.5887(3) 0.5650(2) 0.0280(5) Uani 1 1 d . . .
H10 H 0.3803 0.6859 0.5771 0.034 Uiso 1 1 calc R . .
C11 C 0.2156(4) 0.4793(3) 0.4577(2) 0.0301(6) Uani 1 1 d . . .
H11 H 0.1696 0.4874 0.3842 0.036 Uiso 1 1 calc R . .
C12 C 0.0629(5) 0.2087(3) 0.3883(2) 0.0370(6) Uani 1 1 d . . .
H12A H 0.1448 0.1800 0.3341 0.044 Uiso 1 1 calc R . .
H12B H -0.0763 0.2099 0.3420 0.044 Uiso 1 1 calc R . .
C13 C 0.0282(4) 0.0991(3) 0.4443(2) 0.0314(6) Uani 1 1 d . . .
C14 C 0.1613(5) 0.0104(4) 0.4497(3) 0.0481(8) Uani 1 1 d . . .
H14 H 0.2706 0.0152 0.4150 0.058 Uiso 1 1 calc R . .
C15 C -0.1359(5) 0.0850(4) 0.4946(3) 0.0495(8) Uani 1 1 d . . .
H15 H -0.2311 0.1415 0.4906 0.059 Uiso 1 1 calc R . .
O1W O 0.2549(3) 0.6973(2) 0.87250(17) 0.0303(4) Uani 1 1 d D . .
H1W1 H 0.260(5) 0.775(2) 0.864(3) 0.046(9) Uiso 1 1 d D . .
H1W2 H 0.127(3) 0.653(3) 0.855(2) 0.044(9) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O4 2.0173(18) 1_565 ?
Co1 N1 2.087(2) . ?
Co1 O2 2.1264(18) . ?
Co1 O1W 2.141(2) . ?
Co1 N3 2.198(2) 2_767 ?
Co1 O1 2.2804(19) . ?
O1 C1 1.259(3) . ?
O2 C1 1.273(3) . ?
O3 C5 1.244(3) . ?
O4 C5 1.275(3) . ?
O4 Co1 2.0173(18) 1_545 ?
N1 C9 1.316(3) . ?
N1 C10 1.377(3) . ?
N2 C9 1.350(3) . ?
N2 C11 1.361(3) . ?
N2 C12 1.474(3) . ?
N3 C7 1.435(3) . ?
N3 Co1 2.198(2) 2_767 ?
C1 C2 1.500(3) . ?
C2 C3 1.392(3) . ?
C2 C8 1.399(3) . ?
C3 C4 1.387(3) . ?
C4 C6 1.395(3) . ?
C4 C5 1.506(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.396(3) . ?
C10 C11 1.361(4) . ?
C12 C13 1.509(4) . ?
C13 C14 1.377(4) . ?
C13 C15 1.387(4) . ?
C14 C15 1.375(4) 2_556 ?
C15 C14 1.375(4) 2_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Co1 N1 94.80(8) 1_565 . ?
O4 Co1 O2 158.51(7) 1_565 . ?
N1 Co1 O2 88.60(8) . . ?
O4 Co1 O1W 94.29(8) 1_565 . ?
N1 Co1 O1W 92.40(8) . . ?
O2 Co1 O1W 106.78(7) . . ?
O4 Co1 N3 90.62(8) 1_565 2_767 ?
N1 Co1 N3 172.57(7) . 2_767 ?
O2 Co1 N3 88.20(7) . 2_767 ?
O1W Co1 N3 82.12(8) . 2_767 ?
O4 Co1 O1 98.89(7) 1_565 . ?
N1 Co1 O1 92.51(7) . . ?
O2 Co1 O1 59.71(6) . . ?
O1W Co1 O1 165.49(7) . . ?
N3 Co1 O1 91.66(7) 2_767 . ?
C1 O1 Co1 86.57(13) . . ?
C1 O2 Co1 93.18(13) . . ?
C5 O4 Co1 130.04(16) . 1_545 ?
C9 N1 C10 105.27(19) . . ?
C9 N1 Co1 125.46(16) . . ?
C10 N1 Co1 129.27(17) . . ?
C9 N2 C11 107.1(2) . . ?
C9 N2 C12 127.3(2) . . ?
C11 N2 C12 125.6(2) . . ?
C7 N3 Co1 119.73(13) . 2_767 ?
O1 C1 O2 120.5(2) . . ?
O1 C1 C2 122.0(2) . . ?
O2 C1 C2 117.41(19) . . ?
C3 C2 C8 120.0(2) . . ?
C3 C2 C1 119.2(2) . . ?
C8 C2 C1 120.27(19) . . ?
C4 C3 C2 120.5(2) . . ?
C3 C4 C6 119.4(2) . . ?
C3 C4 C5 120.3(2) . . ?
C6 C4 C5 120.13(19) . . ?
O3 C5 O4 125.7(2) . . ?
O3 C5 C4 118.6(2) . . ?
O4 C5 C4 115.6(2) . . ?
C7 C6 C4 120.5(2) . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 N3 119.65(19) . . ?
C8 C7 N3 120.0(2) . . ?
C7 C8 C2 119.4(2) . . ?
N1 C9 N2 111.7(2) . . ?
C11 C10 N1 109.6(2) . . ?
C10 C11 N2 106.3(2) . . ?
N2 C12 C13 111.8(2) . . ?
C14 C13 C15 117.1(3) . . ?
C14 C13 C12 121.2(3) . . ?
C15 C13 C12 121.6(3) . . ?
C15 C14 C13 121.3(3) 2_556 . ?
C14 C15 C13 121.5(3) 2_556 . ?

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
O1W H1W1 O3 0.823(18) 1.95(2) 2.713(3) 154(3) 1_565
O1W H1W2 O1 0.825(18) 2.020(18) 2.844(3) 177(3) 1_455

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_441
_database_code_depnum_ccdc_archive 'CCDC 1037115'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H38 Mn2 N10 O8'
_chemical_formula_weight         944.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.695(3)
_cell_length_b                   12.743(3)
_cell_length_c                   13.731(3)
_cell_angle_alpha                79.510(4)
_cell_angle_beta                 82.465(6)
_cell_angle_gamma                84.529(5)
_cell_volume                     1989.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             972
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8004
_exptl_absorpt_correction_T_max  0.8894
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'rigaku MM007 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            15767
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.47
_reflns_number_total             8567
_reflns_number_gt                6859
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.1508P)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         8567
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1925
_refine_ls_wR_factor_gt          0.1838
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn -0.11576(3) 0.85146(3) 0.34189(3) 0.02415(14) Uani 1 1 d . . .
Mn2 Mn 0.11683(3) 0.65179(3) 0.14989(3) 0.02419(14) Uani 1 1 d . . .
O1 O 0.04421(15) 0.76052(15) 0.35702(16) 0.0362(5) Uani 1 1 d . . .
O2 O 0.19523(15) 0.69102(16) 0.26854(15) 0.0340(4) Uani 1 1 d . . .
O3 O 0.11654(15) 1.07738(15) 0.51575(15) 0.0344(4) Uani 1 1 d . . .
O4 O 0.27152(16) 1.04437(16) 0.59422(15) 0.0353(4) Uani 1 1 d . . .
O5 O -0.19045(16) 0.83059(15) 0.21207(14) 0.0332(4) Uani 1 1 d . . .
O6 O -0.03934(15) 0.75014(16) 0.13273(16) 0.0362(5) Uani 1 1 d . . .
O7 O -0.12108(15) 0.44261(15) -0.02485(15) 0.0338(4) Uani 1 1 d . . .
O8 O -0.27402(17) 0.46697(16) -0.10702(15) 0.0377(5) Uani 1 1 d . . .
N1 N 0.54354(17) 0.8428(2) 0.35217(19) 0.0407(6) Uani 1 1 d . . .
H1A H 0.5709 0.7963 0.3154 0.049 Uiso 1 1 calc R . .
H1B H 0.5896 0.8807 0.3726 0.049 Uiso 1 1 calc R . .
N2 N -0.54012(18) 0.7142(2) 0.0938(2) 0.0478(7) Uani 1 1 d . . .
H2A H -0.5868 0.6785 0.0716 0.057 Uiso 1 1 calc R . .
H2B H -0.5669 0.7637 0.1274 0.057 Uiso 1 1 calc R . .
N3 N -0.20559(18) 0.70502(18) 0.42140(18) 0.0336(5) Uani 1 1 d . . .
N4 N -0.29406(18) 0.58852(18) 0.53941(18) 0.0332(5) Uani 1 1 d . . .
N5 N -0.91652(18) 0.62024(18) 0.70901(18) 0.0318(5) Uani 1 1 d . . .
N6 N -1.02697(19) 0.48513(19) 0.75378(18) 0.0337(5) Uani 1 1 d . . .
N7 N -0.03536(19) 1.00028(18) 0.25636(18) 0.0315(5) Uani 1 1 d . . .
N8 N 0.06922(18) 1.14017(18) 0.21475(18) 0.0315(5) Uani 1 1 d . . .
N9 N 0.70226(17) 1.11488(18) 0.08205(17) 0.0330(5) Uani 1 1 d . . .
N10 N 0.79672(18) 1.21564(17) -0.04525(17) 0.0313(5) Uani 1 1 d . . .
C1 C 0.1504(2) 0.74970(18) 0.32977(18) 0.0237(5) Uani 1 1 d . . .
C2 C 0.23075(19) 0.81172(18) 0.37140(17) 0.0227(5) Uani 1 1 d . . .
C3 C 0.18611(19) 0.88707(18) 0.43055(17) 0.0229(5) Uani 1 1 d . . .
H3 H 0.1069 0.8961 0.4490 0.027 Uiso 1 1 calc R . .
C4 C 0.2616(2) 0.94908(18) 0.46199(17) 0.0241(5) Uani 1 1 d . . .
C5 C 0.2141(2) 1.02904(19) 0.52763(18) 0.0257(5) Uani 1 1 d . . .
C6 C 0.3795(2) 0.9341(2) 0.43625(19) 0.0275(5) Uani 1 1 d . . .
H6 H 0.4288 0.9760 0.4577 0.033 Uiso 1 1 calc R . .
C7 C 0.42603(19) 0.8568(2) 0.37832(18) 0.0276(5) Uani 1 1 d . . .
C8 C 0.34945(19) 0.79665(19) 0.34628(18) 0.0260(5) Uani 1 1 d . . .
H8 H 0.3783 0.7454 0.3073 0.031 Uiso 1 1 calc R . .
C9 C -0.1457(2) 0.77032(18) 0.15170(18) 0.0240(5) Uani 1 1 d . . .
C10 C -0.22647(19) 0.71872(18) 0.10084(17) 0.0235(5) Uani 1 1 d . . .
C11 C -0.18345(19) 0.63795(18) 0.04692(17) 0.0228(5) Uani 1 1 d . . .
H11 H -0.1043 0.6204 0.0367 0.027 Uiso 1 1 calc R . .
C12 C -0.2607(2) 0.58342(18) 0.00821(17) 0.0251(5) Uani 1 1 d . . .
C13 C -0.2163(2) 0.49225(19) -0.04492(18) 0.0277(5) Uani 1 1 d . . .
C14 C -0.3783(2) 0.6119(2) 0.02113(19) 0.0291(5) Uani 1 1 d . . .
H14 H -0.4286 0.5770 -0.0070 0.035 Uiso 1 1 calc R . .
C15 C -0.42284(19) 0.6921(2) 0.07565(18) 0.0282(5) Uani 1 1 d . . .
C16 C -0.34498(19) 0.74567(19) 0.11438(18) 0.0274(5) Uani 1 1 d . . .
H16 H -0.3729 0.8002 0.1498 0.033 Uiso 1 1 calc R . .
C17 C -0.2421(3) 0.6268(2) 0.3797(2) 0.0443(7) Uani 1 1 d . . .
H17 H -0.2309 0.6234 0.3120 0.053 Uiso 1 1 calc R . .
C18 C -0.2972(3) 0.5546(2) 0.4513(2) 0.0473(8) Uani 1 1 d . . .
H18 H -0.3304 0.4942 0.4420 0.057 Uiso 1 1 calc R . .
C19 C -0.2396(2) 0.6792(2) 0.5174(2) 0.0362(6) Uani 1 1 d . . .
H19 H -0.2271 0.7194 0.5646 0.043 Uiso 1 1 calc R . .
C20 C -0.3517(2) 0.5406(2) 0.6357(2) 0.0406(7) Uani 1 1 d . . .
H20A H -0.3109 0.5556 0.6882 0.049 Uiso 1 1 calc R . .
H20B H -0.3475 0.4636 0.6397 0.049 Uiso 1 1 calc R . .
C21 C -0.4773(2) 0.5815(2) 0.6532(2) 0.0316(6) Uani 1 1 d . . .
C22 C -0.5472(2) 0.5303(2) 0.7337(2) 0.0426(7) Uani 1 1 d . . .
H22 H -0.5168 0.4704 0.7743 0.051 Uiso 1 1 calc R . .
C23 C -0.6615(2) 0.5666(2) 0.7546(2) 0.0410(7) Uani 1 1 d . . .
H23 H -0.7068 0.5310 0.8092 0.049 Uiso 1 1 calc R . .
C24 C -0.7094(2) 0.6553(2) 0.6953(2) 0.0307(5) Uani 1 1 d . . .
C25 C -0.6398(2) 0.7053(2) 0.6144(2) 0.0417(7) Uani 1 1 d . . .
H25 H -0.6706 0.7644 0.5731 0.050 Uiso 1 1 calc R . .
C26 C -0.5254(2) 0.6695(2) 0.5931(2) 0.0427(7) Uani 1 1 d . . .
H26 H -0.4804 0.7047 0.5382 0.051 Uiso 1 1 calc R . .
C27 C -0.8337(2) 0.6972(2) 0.7171(2) 0.0381(6) Uani 1 1 d . . .
H27A H -0.8457 0.7140 0.7840 0.046 Uiso 1 1 calc R . .
H27B H -0.8483 0.7628 0.6708 0.046 Uiso 1 1 calc R . .
C28 C -0.9609(2) 0.5473(2) 0.7850(2) 0.0320(6) Uani 1 1 d . . .
H28 H -0.9467 0.5417 0.8509 0.038 Uiso 1 1 calc R . .
C29 C -0.9572(3) 0.6038(3) 0.6238(2) 0.0415(7) Uani 1 1 d . . .
H29 H -0.9412 0.6420 0.5597 0.050 Uiso 1 1 calc R . .
C30 C -1.0248(3) 0.5210(3) 0.6522(2) 0.0422(7) Uani 1 1 d . . .
H30 H -1.0641 0.4923 0.6098 0.051 Uiso 1 1 calc R . .
C31 C 0.0266(2) 1.0648(2) 0.2894(2) 0.0297(5) Uani 1 1 d . . .
H31 H 0.0392 1.0591 0.3557 0.036 Uiso 1 1 calc R . .
C32 C -0.0316(2) 1.0373(2) 0.1549(2) 0.0371(6) Uani 1 1 d . . .
H32 H -0.0677 1.0073 0.1112 0.045 Uiso 1 1 calc R . .
C33 C 0.0320(2) 1.1230(2) 0.1287(2) 0.0380(7) Uani 1 1 d . . .
H33 H 0.0474 1.1626 0.0651 0.046 Uiso 1 1 calc R . .
C34 C 0.1492(2) 1.2187(2) 0.2242(3) 0.0393(7) Uani 1 1 d . . .
H34A H 0.1328 1.2373 0.2904 0.047 Uiso 1 1 calc R . .
H34B H 0.1352 1.2833 0.1763 0.047 Uiso 1 1 calc R . .
C35 C 0.2751(2) 1.1801(2) 0.2078(2) 0.0302(5) Uani 1 1 d . . .
C36 C 0.3133(2) 1.0779(2) 0.1954(3) 0.0487(8) Uani 1 1 d . . .
H36 H 0.2599 1.0285 0.1947 0.058 Uiso 1 1 calc R . .
C37 C 0.4308(2) 1.0471(2) 0.1841(3) 0.0478(8) Uani 1 1 d . . .
H37 H 0.4547 0.9777 0.1743 0.057 Uiso 1 1 calc R . .
C38 C 0.5121(2) 1.1163(2) 0.1870(2) 0.0349(6) Uani 1 1 d . . .
C39 C 0.4727(2) 1.2210(3) 0.1962(3) 0.0501(8) Uani 1 1 d . . .
H39 H 0.5260 1.2706 0.1964 0.060 Uiso 1 1 calc R . .
C40 C 0.3559(2) 1.2530(2) 0.2052(3) 0.0483(8) Uani 1 1 d . . .
H40 H 0.3318 1.3238 0.2096 0.058 Uiso 1 1 calc R . .
C41 C 0.6395(2) 1.0814(3) 0.1808(2) 0.0435(7) Uani 1 1 d . . .
H41A H 0.6737 1.1108 0.2296 0.052 Uiso 1 1 calc R . .
H41B H 0.6486 1.0040 0.1979 0.052 Uiso 1 1 calc R . .
C42 C 0.7268(3) 1.0555(2) 0.0086(2) 0.0439(7) Uani 1 1 d . . .
H42 H 0.7076 0.9859 0.0109 0.053 Uiso 1 1 calc R . .
C43 C 0.7852(3) 1.1181(2) -0.0692(2) 0.0431(7) Uani 1 1 d . . .
H43 H 0.8133 1.0975 -0.1299 0.052 Uiso 1 1 calc R . .
C44 C 0.7459(2) 1.2101(2) 0.0465(2) 0.0331(6) Uani 1 1 d . . .
H44 H 0.7406 1.2657 0.0827 0.040 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.1183(18) . ?
Mn1 O5 2.1533(19) . ?
Mn1 N7 2.258(2) . ?
Mn1 N3 2.260(2) . ?
Mn1 O3 2.2983(19) 2_576 ?
Mn1 O4 2.3224(19) 2_576 ?
Mn2 O2 2.1262(19) . ?
Mn2 O6 2.1285(18) . ?
Mn2 N10 2.236(2) 2_675 ?
Mn2 N6 2.246(2) 2_466 ?
Mn2 O7 2.2618(19) 2_565 ?
Mn2 O8 2.3508(19) 2_565 ?
Mn2 C13 2.630(2) 2_565 ?
O1 C1 1.252(3) . ?
O2 C1 1.257(3) . ?
O3 C5 1.259(3) . ?
O3 Mn1 2.2983(19) 2_576 ?
O4 C5 1.256(3) . ?
O4 Mn1 2.3224(19) 2_576 ?
O5 C9 1.262(3) . ?
O6 C9 1.249(3) . ?
O7 C13 1.265(3) . ?
O7 Mn2 2.2618(19) 2_565 ?
O8 C13 1.256(3) . ?
O8 Mn2 2.3508(19) 2_565 ?
N1 C7 1.377(3) . ?
N2 C15 1.373(3) . ?
N3 C19 1.316(4) . ?
N3 C17 1.363(4) . ?
N4 C19 1.340(3) . ?
N4 C18 1.363(4) . ?
N4 C20 1.458(3) . ?
N5 C28 1.348(3) . ?
N5 C29 1.376(4) . ?
N5 C27 1.470(3) . ?
N6 C28 1.318(4) . ?
N6 C30 1.384(4) . ?
N6 Mn2 2.246(2) 2_466 ?
N7 C31 1.320(3) . ?
N7 C32 1.383(4) . ?
N8 C31 1.349(3) . ?
N8 C33 1.372(4) . ?
N8 C34 1.467(3) . ?
N9 C44 1.344(3) . ?
N9 C42 1.353(4) . ?
N9 C41 1.465(3) . ?
N10 C44 1.313(3) . ?
N10 C43 1.364(4) . ?
N10 Mn2 2.236(2) 2_675 ?
C1 C2 1.510(3) . ?
C2 C8 1.390(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.395(3) . ?
C4 C6 1.382(3) . ?
C4 C5 1.502(3) . ?
C6 C7 1.403(3) . ?
C7 C8 1.393(3) . ?
C9 C10 1.507(3) . ?
C10 C16 1.392(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.400(3) . ?
C12 C14 1.386(3) . ?
C12 C13 1.498(3) . ?
C13 Mn2 2.630(2) 2_565 ?
C14 C15 1.397(3) . ?
C15 C16 1.398(3) . ?
C17 C18 1.359(4) . ?
C20 C21 1.514(3) . ?
C21 C26 1.385(3) . ?
C21 C22 1.385(4) . ?
C22 C23 1.384(4) . ?
C23 C24 1.386(4) . ?
C24 C25 1.381(4) . ?
C24 C27 1.510(3) . ?
C25 C26 1.384(3) . ?
C29 C30 1.349(4) . ?
C32 C33 1.349(4) . ?
C34 C35 1.509(4) . ?
C35 C36 1.369(4) . ?
C35 C40 1.381(4) . ?
C36 C37 1.389(4) . ?
C37 C38 1.366(4) . ?
C38 C39 1.392(4) . ?
C38 C41 1.510(4) . ?
C39 C40 1.383(4) . ?
C42 C43 1.359(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 O5 112.46(7) . . ?
O1 Mn1 N7 94.69(8) . . ?
O5 Mn1 N7 90.68(8) . . ?
O1 Mn1 N3 88.26(8) . . ?
O5 Mn1 N3 86.19(8) . . ?
N7 Mn1 N3 176.35(8) . . ?
O1 Mn1 O3 94.69(7) . 2_576 ?
O5 Mn1 O3 152.85(7) . 2_576 ?
N7 Mn1 O3 87.58(8) . 2_576 ?
N3 Mn1 O3 94.33(8) . 2_576 ?
O1 Mn1 O4 150.82(8) . 2_576 ?
O5 Mn1 O4 96.17(7) . 2_576 ?
N7 Mn1 O4 90.31(8) . 2_576 ?
N3 Mn1 O4 88.15(8) . 2_576 ?
O3 Mn1 O4 56.76(6) 2_576 2_576 ?
O2 Mn2 O6 109.05(7) . . ?
O2 Mn2 N10 89.51(8) . 2_675 ?
O6 Mn2 N10 85.80(8) . 2_675 ?
O2 Mn2 N6 94.16(9) . 2_466 ?
O6 Mn2 N6 93.70(8) . 2_466 ?
N10 Mn2 N6 176.25(8) 2_675 2_466 ?
O2 Mn2 O7 150.00(7) . 2_565 ?
O6 Mn2 O7 100.89(7) . 2_565 ?
N10 Mn2 O7 90.83(8) 2_675 2_565 ?
N6 Mn2 O7 85.61(8) 2_466 2_565 ?
O2 Mn2 O8 92.93(7) . 2_565 ?
O6 Mn2 O8 157.34(8) . 2_565 ?
N10 Mn2 O8 89.04(8) 2_675 2_565 ?
N6 Mn2 O8 90.02(8) 2_466 2_565 ?
O7 Mn2 O8 57.09(6) 2_565 2_565 ?
O2 Mn2 C13 121.28(8) . 2_565 ?
O6 Mn2 C13 129.61(8) . 2_565 ?
N10 Mn2 C13 92.11(8) 2_675 2_565 ?
N6 Mn2 C13 85.34(8) 2_466 2_565 ?
O7 Mn2 C13 28.73(7) 2_565 2_565 ?
O8 Mn2 C13 28.51(7) 2_565 2_565 ?
C1 O1 Mn1 148.48(18) . . ?
C1 O2 Mn2 126.54(16) . . ?
C5 O3 Mn1 91.01(15) . 2_576 ?
C5 O4 Mn1 89.99(14) . 2_576 ?
C9 O5 Mn1 124.47(16) . . ?
C9 O6 Mn2 152.78(18) . . ?
C13 O7 Mn2 92.01(15) . 2_565 ?
C13 O8 Mn2 88.18(15) . 2_565 ?
C19 N3 C17 104.7(2) . . ?
C19 N3 Mn1 127.8(2) . . ?
C17 N3 Mn1 127.45(19) . . ?
C19 N4 C18 106.5(2) . . ?
C19 N4 C20 127.8(3) . . ?
C18 N4 C20 125.4(2) . . ?
C28 N5 C29 107.4(2) . . ?
C28 N5 C27 125.1(3) . . ?
C29 N5 C27 127.4(2) . . ?
C28 N6 C30 105.4(2) . . ?
C28 N6 Mn2 125.2(2) . 2_466 ?
C30 N6 Mn2 129.3(2) . 2_466 ?
C31 N7 C32 105.1(2) . . ?
C31 N7 Mn1 128.07(19) . . ?
C32 N7 Mn1 126.6(2) . . ?
C31 N8 C33 107.3(2) . . ?
C31 N8 C34 125.4(3) . . ?
C33 N8 C34 127.1(2) . . ?
C44 N9 C42 106.7(2) . . ?
C44 N9 C41 127.0(3) . . ?
C42 N9 C41 126.3(2) . . ?
C44 N10 C43 104.6(2) . . ?
C44 N10 Mn2 131.56(19) . 2_675 ?
C43 N10 Mn2 123.84(19) . 2_675 ?
O1 C1 O2 124.1(2) . . ?
O1 C1 C2 118.6(2) . . ?
O2 C1 C2 117.3(2) . . ?
C8 C2 C3 120.2(2) . . ?
C8 C2 C1 119.5(2) . . ?
C3 C2 C1 120.2(2) . . ?
C2 C3 C4 119.2(2) . . ?
C6 C4 C3 120.3(2) . . ?
C6 C4 C5 120.2(2) . . ?
C3 C4 C5 119.5(2) . . ?
O4 C5 O3 121.7(2) . . ?
O4 C5 C4 119.2(2) . . ?
O3 C5 C4 119.1(2) . . ?
C4 C6 C7 121.1(2) . . ?
N1 C7 C8 121.2(2) . . ?
N1 C7 C6 120.9(2) . . ?
C8 C7 C6 117.9(2) . . ?
C2 C8 C7 121.3(2) . . ?
O6 C9 O5 124.1(2) . . ?
O6 C9 C10 118.4(2) . . ?
O5 C9 C10 117.5(2) . . ?
C16 C10 C11 120.0(2) . . ?
C16 C10 C9 119.9(2) . . ?
C11 C10 C9 119.8(2) . . ?
C10 C11 C12 119.3(2) . . ?
C14 C12 C11 120.1(2) . . ?
C14 C12 C13 119.9(2) . . ?
C11 C12 C13 120.0(2) . . ?
O8 C13 O7 122.0(2) . . ?
O8 C13 C12 119.8(2) . . ?
O7 C13 C12 118.2(2) . . ?
O8 C13 Mn2 63.30(13) . 2_565 ?
O7 C13 Mn2 59.25(13) . 2_565 ?
C12 C13 Mn2 172.47(17) . 2_565 ?
C12 C14 C15 121.2(2) . . ?
N2 C15 C14 120.5(2) . . ?
N2 C15 C16 121.3(2) . . ?
C14 C15 C16 118.1(2) . . ?
C10 C16 C15 121.2(2) . . ?
C18 C17 N3 110.2(3) . . ?
C17 C18 N4 106.2(3) . . ?
N3 C19 N4 112.5(3) . . ?
N4 C20 C21 113.0(2) . . ?
C26 C21 C22 118.2(2) . . ?
C26 C21 C20 122.9(2) . . ?
C22 C21 C20 118.9(2) . . ?
C23 C22 C21 121.1(2) . . ?
C22 C23 C24 120.8(2) . . ?
C25 C24 C23 117.9(2) . . ?
C25 C24 C27 120.3(2) . . ?
C23 C24 C27 121.8(2) . . ?
C24 C25 C26 121.6(2) . . ?
C25 C26 C21 120.5(2) . . ?
N5 C27 C24 112.7(2) . . ?
N6 C28 N5 111.2(3) . . ?
C30 C29 N5 106.0(3) . . ?
C29 C30 N6 110.0(3) . . ?
N7 C31 N8 111.4(2) . . ?
C33 C32 N7 110.1(3) . . ?
C32 C33 N8 106.1(2) . . ?
N8 C34 C35 113.9(2) . . ?
C36 C35 C40 118.5(3) . . ?
C36 C35 C34 124.1(2) . . ?
C40 C35 C34 117.4(2) . . ?
C35 C36 C37 120.8(3) . . ?
C38 C37 C36 121.6(3) . . ?
C37 C38 C39 117.2(3) . . ?
C37 C38 C41 121.8(3) . . ?
C39 C38 C41 121.0(3) . . ?
C40 C39 C38 121.5(3) . . ?
C35 C40 C39 120.2(3) . . ?
N9 C41 C38 113.4(2) . . ?
N9 C42 C43 106.2(3) . . ?
C42 C43 N10 110.2(3) . . ?
N10 C44 N9 112.3(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
N1 H1B O4 0.86 2.10 2.946(3) 168.2 2_676

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         1.463
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.134
####################################################################### 
# 
# 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_1017
_database_code_depnum_ccdc_archive 'CCDC 1037116'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H34 Mn N6 O7'
_chemical_formula_weight         609.54

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   P21/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                   9.888(6)
_cell_length_b                   19.869(12)
_cell_length_c                   15.089(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.072(12)
_cell_angle_gamma                90.00
_cell_volume                     2909(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1276
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'rigaku MM007 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            22426
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.47
_reflns_number_total             6619
_reflns_number_gt                4578
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0687P)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         6619
_refine_ls_number_parameters     393
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.1784
_refine_ls_wR_factor_gt          0.1546
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.178
_refine_ls_shift/su_max          0.015
_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 1.0000 1.0000 0.5000 0.03619(19) Uani 1 2 d S . .
O1 O 1.0057(2) 0.90699(10) 0.42805(13) 0.0456(5) Uani 1 1 d . . .
N1 N 0.7884(3) 0.96947(14) 0.52610(18) 0.0471(7) Uani 1 1 d . . .
C1 C 0.9806(3) 0.89250(14) 0.34478(18) 0.0353(7) Uani 1 1 d . . .
Mn2 Mn 1.0000 0.5000 0.5000 0.0372(2) Uani 1 2 d S . .
O2 O 0.9690(3) 0.93557(10) 0.28258(13) 0.0487(6) Uani 1 1 d . . .
N2 N 0.5796(3) 0.92863(14) 0.5227(2) 0.0540(8) Uani 1 1 d . . .
C2 C 0.9642(3) 0.81843(14) 0.32038(17) 0.0314(6) Uani 1 1 d . . .
O3 O 1.0060(2) 0.59002(10) 0.42012(14) 0.0450(5) Uani 1 1 d . . .
N3 N 0.5732(3) 0.57239(16) 0.4924(3) 0.0691(9) Uani 1 1 d . . .
C3 C 0.9385(3) 0.79830(14) 0.23088(18) 0.0350(7) Uani 1 1 d . . .
H3 H 0.9247 0.8305 0.1853 0.042 Uiso 1 1 calc R . .
O4 O 0.9976(3) 0.67046(11) 0.52190(14) 0.0618(7) Uani 1 1 d . . .
N4 N 0.7832(3) 0.52716(16) 0.5140(2) 0.0589(8) Uani 1 1 d . . .
C4 C 0.9332(3) 0.72931(15) 0.20843(19) 0.0362(7) Uani 1 1 d . . .
O5 O 0.3329(3) 0.87496(16) 0.6908(2) 0.0875(9) Uani 1 1 d . . .
N5 N 0.9117(3) 0.70956(14) 0.11844(15) 0.0512(8) Uani 1 1 d . . .
H5A H 0.9075 0.6675 0.1048 0.061 Uiso 1 1 calc R . .
H5B H 0.9025 0.7394 0.0764 0.061 Uiso 1 1 calc R . .
C5 C 0.9483(3) 0.68204(14) 0.27761(18) 0.0345(6) Uani 1 1 d . . .
H5 H 0.9443 0.6364 0.2636 0.041 Uiso 1 1 calc R . .
N6 N 0.3786(4) 0.76223(19) 0.7041(3) 0.0712(10) Uani 1 1 d . . .
C6 C 0.9695(3) 0.70231(14) 0.36813(18) 0.0317(6) Uani 1 1 d . . .
C7 C 0.9770(3) 0.77074(14) 0.38915(18) 0.0334(6) Uani 1 1 d . . .
H7 H 0.9905 0.7845 0.4491 0.040 Uiso 1 1 calc R . .
C8 C 0.9929(3) 0.65051(15) 0.44223(19) 0.0377(7) Uani 1 1 d . . .
C9 C 0.7606(4) 0.96890(18) 0.6138(2) 0.0531(9) Uani 1 1 d . . .
H9 H 0.8204 0.9839 0.6653 0.064 Uiso 1 1 calc R . .
C10 C 0.6347(4) 0.94346(18) 0.6120(3) 0.0586(10) Uani 1 1 d . . .
H10 H 0.5924 0.9370 0.6613 0.070 Uiso 1 1 calc R . .
C11 C 0.6769(4) 0.94437(17) 0.4737(2) 0.0511(9) Uani 1 1 d . . .
C12 C 0.6561(4) 0.9340(2) 0.3747(2) 0.0658(11) Uani 1 1 d . . .
H12A H 0.6604 0.8868 0.3620 0.099 Uiso 1 1 calc R . .
H12B H 0.7269 0.9573 0.3513 0.099 Uiso 1 1 calc R . .
H12C H 0.5676 0.9513 0.3466 0.099 Uiso 1 1 calc R . .
C13 C 0.4471(4) 0.89707(18) 0.4905(3) 0.0602(10) Uani 1 1 d . . .
H13A H 0.4067 0.9164 0.4324 0.072 Uiso 1 1 calc R . .
H13B H 0.3866 0.9075 0.5322 0.072 Uiso 1 1 calc R . .
C14 C 0.4532(4) 0.82167(18) 0.4804(2) 0.0513(8) Uani 1 1 d . . .
C15 C 0.3340(4) 0.7871(2) 0.4499(3) 0.0712(12) Uani 1 1 d . . .
H15 H 0.2513 0.8104 0.4342 0.085 Uiso 1 1 calc R . .
C16 C 0.3351(4) 0.7182(2) 0.4422(3) 0.0739(12) Uani 1 1 d . . .
H16 H 0.2527 0.6957 0.4212 0.089 Uiso 1 1 calc R . .
C17 C 0.4549(4) 0.68171(19) 0.4648(3) 0.0585(10) Uani 1 1 d . . .
C18 C 0.5750(4) 0.71621(19) 0.4939(3) 0.0622(10) Uani 1 1 d . . .
H18 H 0.6577 0.6927 0.5082 0.075 Uiso 1 1 calc R . .
C19 C 0.5753(4) 0.78564(19) 0.5024(3) 0.0616(10) Uani 1 1 d . . .
H19 H 0.6578 0.8082 0.5228 0.074 Uiso 1 1 calc R . .
C20 C 0.4473(4) 0.6059(2) 0.4557(3) 0.0756(13) Uani 1 1 d . . .
H20A H 0.3756 0.5894 0.4860 0.091 Uiso 1 1 calc R . .
H20B H 0.4210 0.5945 0.3923 0.091 Uiso 1 1 calc R . .
C21 C 0.6799(4) 0.55061(18) 0.4559(3) 0.0608(10) Uani 1 1 d . . .
C22 C 0.7439(5) 0.5351(2) 0.5995(3) 0.0669(11) Uani 1 1 d . . .
H22 H 0.7973 0.5232 0.6550 0.080 Uiso 1 1 calc R . .
C23 C 0.6198(5) 0.5621(2) 0.5874(3) 0.0797(13) Uani 1 1 d . . .
H23 H 0.5711 0.5725 0.6325 0.096 Uiso 1 1 calc R . .
C24 C 0.6731(5) 0.5525(3) 0.3568(3) 0.0856(14) Uani 1 1 d . . .
H24A H 0.7106 0.5943 0.3406 0.128 Uiso 1 1 calc R . .
H24B H 0.5789 0.5486 0.3263 0.128 Uiso 1 1 calc R . .
H24C H 0.7255 0.5158 0.3394 0.128 Uiso 1 1 calc R . .
C25 C 0.5252(5) 0.7695(3) 0.7350(3) 0.0923(15) Uani 1 1 d . . .
H25A H 0.5490 0.7570 0.7976 0.138 Uiso 1 1 calc R . .
H25B H 0.5512 0.8155 0.7281 0.138 Uiso 1 1 calc R . .
H25C H 0.5731 0.7409 0.7001 0.138 Uiso 1 1 calc R . .
C26 C 0.3236(6) 0.6946(3) 0.6948(4) 0.1122(19) Uani 1 1 d . . .
H26A H 0.2276 0.6962 0.6677 0.168 Uiso 1 1 calc R . .
H26B H 0.3346 0.6741 0.7533 0.168 Uiso 1 1 calc R . .
H26C H 0.3723 0.6687 0.6573 0.168 Uiso 1 1 calc R . .
C27 C 0.2976(5) 0.8151(3) 0.6855(3) 0.0815(13) Uani 1 1 d . . .
H27 H 0.2041 0.8066 0.6663 0.098 Uiso 1 1 calc R . .
O1W O 0.9150(3) 1.05193(13) 0.36781(16) 0.0512(6) Uani 1 1 d D . .
O2W O 1.0775(3) 0.56272(12) 0.62288(15) 0.0519(6) Uani 1 1 d D . .
H3W H 1.056(4) 0.6002(12) 0.598(2) 0.063(12) Uiso 1 1 d D . .
H4W H 1.055(4) 0.5630(19) 0.6745(16) 0.069(12) Uiso 1 1 d D . .
H1W H 0.839(3) 1.071(2) 0.353(3) 0.108(19) Uiso 1 1 d D . .
H2W H 0.917(4) 1.0196(15) 0.330(2) 0.080(14) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.150(2) 3_776 ?
Mn1 O1 2.150(2) . ?
Mn1 O1W 2.260(3) 3_776 ?
Mn1 O1W 2.260(3) . ?
Mn1 N1 2.284(3) . ?
Mn1 N1 2.284(3) 3_776 ?
O1 C1 1.266(3) . ?
N1 C11 1.325(4) . ?
N1 C9 1.403(4) . ?
C1 O2 1.259(3) . ?
C1 C2 1.518(4) . ?
Mn2 O3 2.164(2) 3_766 ?
Mn2 O3 2.164(2) . ?
Mn2 O2W 2.243(3) 3_766 ?
Mn2 O2W 2.243(3) . ?
Mn2 N4 2.259(3) . ?
Mn2 N4 2.259(3) 3_766 ?
N2 C11 1.357(4) . ?
N2 C10 1.386(5) . ?
N2 C13 1.450(5) . ?
C2 C3 1.384(4) . ?
C2 C7 1.393(4) . ?
O3 C8 1.261(3) . ?
N3 C21 1.351(5) . ?
N3 C20 1.427(5) . ?
N3 C23 1.434(5) . ?
C3 C4 1.410(4) . ?
O4 C8 1.258(3) . ?
N4 C21 1.297(5) . ?
N4 C22 1.427(5) . ?
C4 N5 1.390(3) . ?
C4 C5 1.391(4) . ?
O5 C27 1.237(5) . ?
C5 C6 1.401(4) . ?
N6 C27 1.318(5) . ?
N6 C25 1.443(6) . ?
N6 C26 1.445(6) . ?
C6 C7 1.395(4) . ?
C6 C8 1.505(4) . ?
C9 C10 1.339(5) . ?
C11 C12 1.483(5) . ?
C13 C14 1.508(5) . ?
C14 C15 1.366(5) . ?
C14 C19 1.388(5) . ?
C15 C16 1.374(6) . ?
C16 C17 1.375(5) . ?
C17 C18 1.369(5) . ?
C17 C20 1.513(5) . ?
C18 C19 1.385(5) . ?
C21 C24 1.485(5) . ?
C22 C23 1.319(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O1 180.000(1) 3_776 . ?
O1 Mn1 O1W 89.32(9) 3_776 3_776 ?
O1 Mn1 O1W 90.68(9) . 3_776 ?
O1 Mn1 O1W 90.68(9) 3_776 . ?
O1 Mn1 O1W 89.32(9) . . ?
O1W Mn1 O1W 180.000(1) 3_776 . ?
O1 Mn1 N1 91.57(9) 3_776 . ?
O1 Mn1 N1 88.43(9) . . ?
O1W Mn1 N1 85.65(10) 3_776 . ?
O1W Mn1 N1 94.35(10) . . ?
O1 Mn1 N1 88.43(9) 3_776 3_776 ?
O1 Mn1 N1 91.57(9) . 3_776 ?
O1W Mn1 N1 94.35(10) 3_776 3_776 ?
O1W Mn1 N1 85.65(10) . 3_776 ?
N1 Mn1 N1 180.00(4) . 3_776 ?
C1 O1 Mn1 132.64(18) . . ?
C11 N1 C9 105.6(3) . . ?
C11 N1 Mn1 133.0(2) . . ?
C9 N1 Mn1 121.1(2) . . ?
O2 C1 O1 123.9(3) . . ?
O2 C1 C2 119.2(2) . . ?
O1 C1 C2 116.9(2) . . ?
O3 Mn2 O3 180.00(10) 3_766 . ?
O3 Mn2 O2W 87.68(9) 3_766 3_766 ?
O3 Mn2 O2W 92.32(9) . 3_766 ?
O3 Mn2 O2W 92.32(9) 3_766 . ?
O3 Mn2 O2W 87.68(9) . . ?
O2W Mn2 O2W 180.000(1) 3_766 . ?
O3 Mn2 N4 90.99(10) 3_766 . ?
O3 Mn2 N4 89.01(10) . . ?
O2W Mn2 N4 91.71(11) 3_766 . ?
O2W Mn2 N4 88.29(11) . . ?
O3 Mn2 N4 89.01(10) 3_766 3_766 ?
O3 Mn2 N4 90.99(10) . 3_766 ?
O2W Mn2 N4 88.29(11) 3_766 3_766 ?
O2W Mn2 N4 91.71(11) . 3_766 ?
N4 Mn2 N4 180.00(16) . 3_766 ?
C11 N2 C10 107.1(3) . . ?
C11 N2 C13 127.4(3) . . ?
C10 N2 C13 125.4(3) . . ?
C3 C2 C7 120.2(3) . . ?
C3 C2 C1 120.5(2) . . ?
C7 C2 C1 119.2(2) . . ?
C8 O3 Mn2 128.70(18) . . ?
C21 N3 C20 133.1(4) . . ?
C21 N3 C23 103.6(3) . . ?
C20 N3 C23 122.9(4) . . ?
C2 C3 C4 120.4(2) . . ?
C21 N4 C22 104.8(4) . . ?
C21 N4 Mn2 131.4(3) . . ?
C22 N4 Mn2 122.6(3) . . ?
N5 C4 C5 121.1(3) . . ?
N5 C4 C3 120.0(3) . . ?
C5 C4 C3 118.8(3) . . ?
C4 C5 C6 120.8(3) . . ?
C27 N6 C25 121.3(4) . . ?
C27 N6 C26 121.2(5) . . ?
C25 N6 C26 117.4(4) . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 C8 120.3(2) . . ?
C5 C6 C8 120.1(2) . . ?
C2 C7 C6 120.0(2) . . ?
O4 C8 O3 124.5(3) . . ?
O4 C8 C6 117.8(3) . . ?
O3 C8 C6 117.7(2) . . ?
C10 C9 N1 109.5(3) . . ?
C9 C10 N2 106.9(3) . . ?
N1 C11 N2 111.0(3) . . ?
N1 C11 C12 126.3(3) . . ?
N2 C11 C12 122.8(3) . . ?
N2 C13 C14 114.4(3) . . ?
C15 C14 C19 118.4(3) . . ?
C15 C14 C13 119.0(3) . . ?
C19 C14 C13 122.5(3) . . ?
C14 C15 C16 120.6(3) . . ?
C15 C16 C17 121.7(3) . . ?
C18 C17 C16 118.0(4) . . ?
C18 C17 C20 123.5(3) . . ?
C16 C17 C20 118.5(3) . . ?
C17 C18 C19 121.0(3) . . ?
C18 C19 C14 120.3(3) . . ?
N3 C20 C17 113.9(3) . . ?
N4 C21 N3 114.6(4) . . ?
N4 C21 C24 124.5(4) . . ?
N3 C21 C24 120.9(4) . . ?
C23 C22 N4 109.1(4) . . ?
C22 C23 N3 108.0(4) . . ?
O5 C27 N6 126.9(5) . . ?

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
N5 H5B O4 0.86 2.25 3.000(4) 145.7 4_575
O2W H3W O4 0.844(18) 1.83(2) 2.658(3) 168(4) .
O2W H4W O2 0.847(18) 1.982(19) 2.820(3) 170(4) 4_576
O1W H1W O5 0.835(19) 2.01(2) 2.841(4) 173(5) 3_676
O1W H2W O2 0.862(19) 1.92(2) 2.747(3) 159(4) .
N5 H5B O4 0.86 2.25 3.000(4) 145.7 4_575
C9 H9 O2 0.93 2.62 3.404(5) 141.8 3_776
C12 H12B O1W 0.96 2.62 3.486(5) 149.7 .
C13 H13B O5 0.97 2.63 3.451(5) 142.6 .
C22 H22 O2 0.93 2.45 3.250(5) 144.0 4_576
C24 H24C O2W 0.96 2.47 3.335(6) 149.2 3_766
O2W H3W O3 0.844(18) 2.64(3) 3.053(4) 112(3) .
O2W H3W O4 0.844(18) 1.83(2) 2.658(3) 168(4) .
O2W H4W O2 0.847(18) 1.982(19) 2.820(3) 170(4) 4_576
O1W H1W O5 0.835(19) 2.01(2) 2.841(4) 173(5) 3_676
O1W H2W O2 0.862(19) 1.92(2) 2.747(3) 159(4) .

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_1200
_database_code_depnum_ccdc_archive 'CCDC 1037117'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Co N3 O5'
_chemical_formula_weight         389.25

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   P21/c

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

_cell_length_a                   12.8113(10)
_cell_length_b                   7.8747(6)
_cell_length_c                   15.8919(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.871(8)
_cell_angle_gamma                90.00
_cell_volume                     1603.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_T_max  0.8260
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'rigaku MM007 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12196
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3646
_reflns_number_gt                3283
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0467P)²+0.1627P] 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         3646
_refine_ls_number_parameters     235
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.008
_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
Co1 Co 0.334635(17) 0.01150(3) 0.719458(13) 0.02363(10) Uani 1 1 d . . .
O1 O 0.36623(10) 0.23753(14) 1.21288(7) 0.0309(3) Uani 1 1 d . . .
O2 O 0.34436(10) 0.34330(14) 1.08574(8) 0.0326(3) Uani 1 1 d . . .
O3 O 0.39211(11) -0.30718(16) 0.85132(8) 0.0373(3) Uani 1 1 d . . .
O4 O 0.33835(11) -0.03763(16) 0.84015(8) 0.0331(3) Uani 1 1 d . . .
N1 N 0.46194(11) -0.38313(16) 1.16851(8) 0.0246(3) Uani 1 1 d . . .
H1A H 0.5018 -0.3408 1.2107 0.030 Uiso 1 1 calc R . .
H1B H 0.5010 -0.4572 1.1396 0.030 Uiso 1 1 calc R . .
N2 N 0.18453(12) -0.0318(2) 0.68233(10) 0.0331(3) Uani 1 1 d . . .
N3 N 0.03236(12) -0.1515(2) 0.65781(11) 0.0384(4) Uani 1 1 d . . .
C1 C 0.36199(12) 0.2193(2) 1.13253(11) 0.0256(3) Uani 1 1 d . . .
C2 C 0.37803(12) 0.0458(2) 1.09606(10) 0.0234(3) Uani 1 1 d . . .
C3 C 0.41023(12) -0.0875(2) 1.14817(10) 0.0237(3) Uani 1 1 d . . .
H3 H 0.4184 -0.0704 1.2058 0.028 Uiso 1 1 calc R . .
C4 C 0.43000(12) -0.24619(19) 1.11330(10) 0.0224(3) Uani 1 1 d . . .
C5 C 0.41617(13) -0.27172(19) 1.02765(10) 0.0242(3) Uani 1 1 d . . .
H5 H 0.4297 -0.3779 1.0046 0.029 Uiso 1 1 calc R . .
C6 C 0.38211(12) -0.13931(19) 0.97570(10) 0.0227(3) Uani 1 1 d . . .
C7 C 0.36377(13) 0.01954(19) 1.01005(11) 0.0234(3) Uani 1 1 d . . .
H7 H 0.3419 0.1086 0.9756 0.028 Uiso 1 1 calc R . .
C8 C 0.37088(12) -0.1667(2) 0.88207(10) 0.0245(3) Uani 1 1 d . . .
C9 C 0.16337(17) -0.3269(3) 0.73862(16) 0.0503(5) Uani 1 1 d . . .
H9A H 0.2346 -0.3133 0.7571 0.075 Uiso 1 1 calc R . .
H9B H 0.1583 -0.4219 0.7009 0.075 Uiso 1 1 calc R . .
H9C H 0.1201 -0.3466 0.7864 0.075 Uiso 1 1 calc R . .
C10 C 0.12807(14) -0.1704(2) 0.69434(12) 0.0344(4) Uani 1 1 d . . .
C11 C 0.12203(15) 0.0787(3) 0.63592(13) 0.0405(4) Uani 1 1 d . . .
H11 H 0.1415 0.1868 0.6185 0.049 Uiso 1 1 calc R . .
C12 C 0.02882(17) 0.0054(2) 0.61995(15) 0.0419(5) Uani 1 1 d . . .
H12 H -0.0268 0.0516 0.5894 0.050 Uiso 1 1 calc R . .
C13 C -0.04499(15) -0.2853(3) 0.64459(14) 0.0456(5) Uani 1 1 d . . .
H13A H -0.1133 -0.2343 0.6361 0.055 Uiso 1 1 calc R . .
H13B H -0.0477 -0.3561 0.6945 0.055 Uiso 1 1 calc R . .
C14 C -0.01956(14) -0.3948(3) 0.56919(13) 0.0389(4) Uani 1 1 d . . .
C15 C -0.08739(17) -0.5251(3) 0.54822(16) 0.0473(5) Uani 1 1 d . . .
H15 H -0.1467 -0.5426 0.5801 0.057 Uiso 1 1 calc R . .
C16 C 0.06791(16) -0.3701(3) 0.51984(15) 0.0497(6) Uani 1 1 d . . .
H16 H 0.1139 -0.2821 0.5327 0.060 Uiso 1 1 calc R . .
O1W O 0.2339(2) 0.4608(4) 0.93122(17) 0.0919(8) Uani 1 1 d D . .
H1W1 H 0.269(3) 0.423(5) 0.9724(18) 0.108(13) Uiso 1 1 d D . .
H1W2 H 0.282(3) 0.494(5) 0.901(3) 0.129(19) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O4 1.9566(12) . ?
Co1 O1 2.0204(12) 4_565 ?
Co1 N2 2.0317(16) . ?
Co1 N1 2.0922(14) 4 ?
O1 C1 1.285(2) . ?
O1 Co1 2.0204(12) 4_566 ?
O2 C1 1.2462(19) . ?
O3 C8 1.241(2) . ?
O4 C8 1.2815(19) . ?
N1 C4 1.4455(19) . ?
N1 Co1 2.0923(14) 4_556 ?
N2 C10 1.325(2) . ?
N2 C11 1.387(2) . ?
N3 C10 1.357(2) . ?
N3 C12 1.374(3) . ?
N3 C13 1.460(2) . ?
C1 C2 1.499(2) . ?
C2 C7 1.392(2) . ?
C2 C3 1.396(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.385(2) . ?
C5 C6 1.396(2) . ?
C6 C7 1.386(2) . ?
C6 C8 1.508(2) . ?
C9 C10 1.486(3) . ?
C11 C12 1.347(3) . ?
C13 C14 1.516(3) . ?
C14 C15 1.382(3) . ?
C14 C16 1.391(3) . ?
C15 C16 1.386(3) 3_546 ?
C16 C15 1.386(3) 3_546 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Co1 O1 104.02(5) . 4_565 ?
O4 Co1 N2 105.09(6) . . ?
O1 Co1 N2 109.79(6) 4_565 . ?
O4 Co1 N1 106.04(5) . 4 ?
O1 Co1 N1 107.14(5) 4_565 4 ?
N2 Co1 N1 123.13(6) . 4 ?
C1 O1 Co1 98.94(10) . 4_566 ?
C8 O4 Co1 132.01(11) . . ?
C4 N1 Co1 112.34(10) . 4_556 ?
C10 N2 C11 106.34(16) . . ?
C10 N2 Co1 127.80(13) . . ?
C11 N2 Co1 125.82(13) . . ?
C10 N3 C12 108.05(16) . . ?
C10 N3 C13 126.10(18) . . ?
C12 N3 C13 124.62(17) . . ?
O2 C1 O1 120.64(15) . . ?
O2 C1 C2 120.53(15) . . ?
O1 C1 C2 118.83(14) . . ?
C7 C2 C3 120.27(15) . . ?
C7 C2 C1 119.91(14) . . ?
C3 C2 C1 119.80(15) . . ?
C4 C3 C2 119.55(15) . . ?
C5 C4 C3 120.03(14) . . ?
C5 C4 N1 121.28(14) . . ?
C3 C4 N1 118.66(14) . . ?
C4 C5 C6 120.48(14) . . ?
C7 C6 C5 119.63(14) . . ?
C7 C6 C8 120.22(14) . . ?
C5 C6 C8 120.06(14) . . ?
C6 C7 C2 120.03(14) . . ?
O3 C8 O4 125.02(15) . . ?
O3 C8 C6 119.85(14) . . ?
O4 C8 C6 115.13(14) . . ?
N2 C10 N3 109.85(17) . . ?
N2 C10 C9 126.05(17) . . ?
N3 C10 C9 124.08(17) . . ?
C12 C11 N2 109.52(18) . . ?
C11 C12 N3 106.23(18) . . ?
N3 C13 C14 111.77(17) . . ?
C15 C14 C16 118.47(19) . . ?
C15 C14 C13 118.10(18) . . ?
C16 C14 C13 123.42(18) . . ?
C14 C15 C16 120.7(2) . 3_546 ?
C15 C16 C14 120.85(19) 3_546 . ?

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
N1 H1A O1 0.90 2.16 3.0291(18) 163.0 2_647
N1 H1B O3 0.90 2.31 3.0920(18) 145.4 3_647
O1W H1W1 O2 0.842(19) 2.13(2) 2.963(3) 173(4) .
O1W H1W2 O3 0.825(19) 2.26(2) 3.023(3) 153(4) 1_565

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_1876
_database_code_depnum_ccdc_archive 'CCDC 1037118'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 Mn N4 O4'
_chemical_formula_weight         444.33

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   P21/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                   10.4640(19)
_cell_length_b                   11.5072(12)
_cell_length_c                   16.689(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.865(8)
_cell_angle_gamma                90.00
_cell_volume                     1959.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7312
_exptl_absorpt_correction_T_max  0.8948
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'rigaku MM007 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14947
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4467
_reflns_number_gt                3865
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0444P)²+0.2427P] 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         4467
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.090
_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 0.24690(2) 0.06518(2) 0.241739(16) 0.02513(10) Uani 1 1 d . . .
O1 O -0.09124(12) -0.30531(11) 0.30521(8) 0.0342(3) Uani 1 1 d . . .
O2 O -0.03915(13) -0.46012(11) 0.24177(8) 0.0337(3) Uani 1 1 d . . .
O3 O 0.42541(15) -0.50654(14) 0.20163(11) 0.0571(5) Uani 1 1 d . . .
O4 O 0.57461(13) -0.40037(13) 0.28754(9) 0.0389(3) Uani 1 1 d . . .
N1 N 0.08508(19) -0.18332(15) 0.04843(10) 0.0414(4) Uani 1 1 d . . .
N2 N 0.19835(18) -0.06312(14) 0.14046(10) 0.0375(4) Uani 1 1 d . . .
N3 N 0.30389(17) 0.17839(14) 0.35903(10) 0.0358(4) Uani 1 1 d . . .
N4 N 0.32711(15) -0.05480(12) 0.35098(9) 0.0253(3) Uani 1 1 d . . .
H4 H 0.4160 -0.0515 0.3591 0.030 Uiso 1 1 calc R . .
C1 C 0.0723(2) -0.43720(18) 0.06489(12) 0.0422(5) Uani 1 1 d . . .
H1 H 0.1216 -0.3956 0.1088 0.051 Uiso 1 1 calc R . .
C2 C -0.0808(2) -0.44242(18) -0.06437(12) 0.0410(5) Uani 1 1 d . . .
H2 H -0.1353 -0.4042 -0.1081 0.049 Uiso 1 1 calc R . .
C3 C -0.0086(2) -0.37834(18) 0.00109(11) 0.0368(5) Uani 1 1 d . . .
C4 C -0.0281(2) -0.24860(19) 0.00158(13) 0.0481(6) Uani 1 1 d . . .
H4A H -0.0478 -0.2209 -0.0547 0.058 Uiso 1 1 calc R . .
H4B H -0.1036 -0.2321 0.0245 0.058 Uiso 1 1 calc R . .
C5 C 0.2073(3) -0.1750(2) 0.03281(16) 0.0613(7) Uani 1 1 d . . .
H5 H 0.2375 -0.2126 -0.0087 0.074 Uiso 1 1 calc R . .
C6 C 0.2759(2) -0.1012(2) 0.08956(15) 0.0548(6) Uani 1 1 d . . .
H6 H 0.3627 -0.0795 0.0934 0.066 Uiso 1 1 calc R . .
C7 C 0.0852(2) -0.11525(18) 0.11382(12) 0.0397(5) Uani 1 1 d . . .
H7 H 0.0133 -0.1061 0.1375 0.048 Uiso 1 1 calc R . .
C8 C 0.3222(3) 0.29377(18) 0.36009(14) 0.0491(6) Uani 1 1 d . . .
H8 H 0.3097 0.3333 0.3103 0.059 Uiso 1 1 calc R . .
C9 C 0.3591(3) 0.35624(19) 0.43247(15) 0.0561(7) Uani 1 1 d . . .
H9 H 0.3699 0.4364 0.4313 0.067 Uiso 1 1 calc R . .
C10 C 0.3795(2) 0.2980(2) 0.50602(15) 0.0536(6) Uani 1 1 d . . .
H10 H 0.4048 0.3382 0.5554 0.064 Uiso 1 1 calc R . .
C11 C 0.3622(2) 0.17899(19) 0.50581(13) 0.0437(5) Uani 1 1 d . . .
H11 H 0.3767 0.1377 0.5549 0.052 Uiso 1 1 calc R . .
C12 C 0.32255(19) 0.12196(16) 0.43087(11) 0.0322(4) Uani 1 1 d . . .
C13 C 0.2956(2) -0.00690(16) 0.42576(11) 0.0354(4) Uani 1 1 d . . .
H13A H 0.3483 -0.0453 0.4737 0.043 Uiso 1 1 calc R . .
H13B H 0.2040 -0.0210 0.4251 0.043 Uiso 1 1 calc R . .
C14 C 0.29198(17) -0.17289(14) 0.32985(10) 0.0237(3) Uani 1 1 d . . .
C15 C 0.16401(17) -0.21246(15) 0.32193(10) 0.0245(4) Uani 1 1 d . . .
H15 H 0.1010 -0.1647 0.3363 0.029 Uiso 1 1 calc R . .
C16 C 0.13100(16) -0.32444(14) 0.29222(10) 0.0234(3) Uani 1 1 d . . .
C17 C 0.22549(17) -0.39595(15) 0.27009(10) 0.0249(4) Uani 1 1 d . . .
H17 H 0.2030 -0.4702 0.2499 0.030 Uiso 1 1 calc R . .
C18 C 0.35293(17) -0.35607(15) 0.27835(10) 0.0258(4) Uani 1 1 d . . .
C19 C 0.38550(17) -0.24468(15) 0.30847(10) 0.0261(4) Uani 1 1 d . . .
H19 H 0.4710 -0.2181 0.3143 0.031 Uiso 1 1 calc R . .
C20 C -0.00789(17) -0.36600(15) 0.27890(10) 0.0254(4) Uani 1 1 d . . .
C21 C 0.45782(19) -0.42843(16) 0.25280(12) 0.0315(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 O4 2.0714(13) 2_655 ?
Mn1 N2 2.2164(16) . ?
Mn1 O1 2.2180(13) 2 ?
Mn1 O2 2.2699(13) 2 ?
Mn1 N4 2.2920(15) . ?
Mn1 N3 2.3162(16) . ?
Mn1 C20 2.5724(18) 2 ?
O1 C20 1.269(2) . ?
O1 Mn1 2.2180(13) 2_545 ?
O2 C20 1.254(2) . ?
O2 Mn1 2.2700(13) 2_545 ?
O3 C21 1.234(2) . ?
O4 C21 1.272(2) . ?
O4 Mn1 2.0713(13) 2_645 ?
N1 C7 1.343(2) . ?
N1 C5 1.364(3) . ?
N1 C4 1.472(3) . ?
N2 C7 1.314(3) . ?
N2 C6 1.371(3) . ?
N3 C12 1.339(2) . ?
N3 C8 1.341(2) . ?
N4 C14 1.431(2) . ?
N4 C13 1.467(2) . ?
C1 C3 1.381(3) . ?
C1 C2 1.388(3) 3_545 ?
C2 C1 1.388(3) 3_545 ?
C2 C3 1.393(3) . ?
C3 C4 1.507(3) . ?
C5 C6 1.353(3) . ?
C8 C9 1.385(3) . ?
C9 C10 1.373(3) . ?
C10 C11 1.382(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.508(3) . ?
C14 C19 1.387(2) . ?
C14 C15 1.393(2) . ?
C15 C16 1.396(2) . ?
C16 C17 1.398(2) . ?
C16 C20 1.499(2) . ?
C17 C18 1.388(2) . ?
C18 C19 1.391(2) . ?
C18 C21 1.513(2) . ?
C20 Mn1 2.5724(18) 2_545 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Mn1 N2 90.76(6) 2_655 . ?
O4 Mn1 O1 114.70(5) 2_655 2 ?
N2 Mn1 O1 98.78(6) . 2 ?
O4 Mn1 O2 172.43(5) 2_655 2 ?
N2 Mn1 O2 86.78(6) . 2 ?
O1 Mn1 O2 58.75(5) 2 2 ?
O4 Mn1 N4 96.50(6) 2_655 . ?
N2 Mn1 N4 100.75(6) . . ?
O1 Mn1 N4 142.73(5) 2 . ?
O2 Mn1 N4 90.99(5) 2 . ?
O4 Mn1 N3 90.90(6) 2_655 . ?
N2 Mn1 N3 172.45(6) . . ?
O1 Mn1 N3 87.21(6) 2 . ?
O2 Mn1 N3 92.46(6) 2 . ?
N4 Mn1 N3 71.75(5) . . ?
O4 Mn1 C20 144.13(6) 2_655 2 ?
N2 Mn1 C20 92.98(6) . 2 ?
O1 Mn1 C20 29.57(5) 2 2 ?
O2 Mn1 C20 29.18(5) 2 2 ?
N4 Mn1 C20 117.70(5) . 2 ?
N3 Mn1 C20 89.98(6) . 2 ?
C20 O1 Mn1 90.87(11) . 2_545 ?
C20 O2 Mn1 88.90(10) . 2_545 ?
C21 O4 Mn1 132.00(13) . 2_645 ?
C7 N1 C5 106.45(17) . . ?
C7 N1 C4 125.74(19) . . ?
C5 N1 C4 127.74(18) . . ?
C7 N2 C6 104.95(17) . . ?
C7 N2 Mn1 126.77(14) . . ?
C6 N2 Mn1 128.20(15) . . ?
C12 N3 C8 118.46(18) . . ?
C12 N3 Mn1 116.28(12) . . ?
C8 N3 Mn1 125.25(14) . . ?
C14 N4 C13 118.19(14) . . ?
C14 N4 Mn1 110.33(10) . . ?
C13 N4 Mn1 109.79(11) . . ?
C3 C1 C2 120.93(18) . 3_545 ?
C1 C2 C3 120.6(2) 3_545 . ?
C1 C3 C2 118.5(2) . . ?
C1 C3 C4 122.84(18) . . ?
C2 C3 C4 118.5(2) . . ?
N1 C4 C3 114.47(19) . . ?
C6 C5 N1 106.53(19) . . ?
C5 C6 N2 109.8(2) . . ?
N2 C7 N1 112.26(18) . . ?
N3 C8 C9 122.5(2) . . ?
C10 C9 C8 119.0(2) . . ?
C9 C10 C11 119.2(2) . . ?
C10 C11 C12 118.9(2) . . ?
N3 C12 C11 122.07(18) . . ?
N3 C12 C13 115.97(16) . . ?
C11 C12 C13 121.95(18) . . ?
N4 C13 C12 110.06(15) . . ?
C19 C14 C15 119.97(16) . . ?
C19 C14 N4 118.16(15) . . ?
C15 C14 N4 121.51(15) . . ?
C14 C15 C16 119.48(15) . . ?
C15 C16 C17 120.24(16) . . ?
C15 C16 C20 120.15(15) . . ?
C17 C16 C20 119.51(15) . . ?
C18 C17 C16 119.98(16) . . ?
C17 C18 C19 119.55(16) . . ?
C17 C18 C21 122.10(16) . . ?
C19 C18 C21 118.31(16) . . ?
C14 C19 C18 120.78(16) . . ?
O2 C20 O1 121.47(16) . . ?
O2 C20 C16 119.10(15) . . ?
O1 C20 C16 119.43(16) . . ?
O2 C20 Mn1 61.92(9) . 2_545 ?
O1 C20 Mn1 59.56(9) . 2_545 ?
C16 C20 Mn1 178.92(13) . 2_545 ?
O3 C21 O4 126.04(18) . . ?
O3 C21 C18 119.41(18) . . ?
O4 C21 C18 114.55(17) . . ?

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
N4 H4 O3 0.91 2.19 2.966(2) 142.7 2_655

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.054
