# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2juld1_0m
_database_code_depnum_ccdc_archive 'CCDC 1405365'
_audit_update_record             
;
2015-06-06 deposited with the CCDC.
2016-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Co N3 O10'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Red

_diffrn_ambient_temperature      273(2)
_chemical_formula_weight         515.27

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   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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

_cell_length_a                   15.020(7)
_cell_length_b                   9.275(4)
_cell_length_c                   15.524(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.849(7)
_cell_angle_gamma                90.00
_cell_volume                     2157.8(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      1.18
_cell_measurement_theta_max      25.0
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.7888
_exptl_absorpt_correction_T_max  0.8748
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10591
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3794
_reflns_number_gt                2783
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1020P)²+1.1677P] 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         3794
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1903
_refine_ls_wR_factor_gt          0.1692
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1883(3) 0.1668(4) 0.1791(3) 0.0396(9) Uani 1 1 d . . .
C2 C 0.2710(3) 0.0841(5) 0.2120(3) 0.0505(11) Uani 1 1 d . . .
C3 C 0.1042(3) 0.1594(5) 0.2071(3) 0.0511(11) Uani 1 1 d . . .
H3 H 0.0911 0.0977 0.2517 0.061 Uiso 1 1 calc R . .
C4 C 0.0385(3) 0.2470(5) 0.1668(3) 0.0521(12) Uani 1 1 d . . .
H1 H -0.0194 0.2440 0.1846 0.062 Uiso 1 1 calc R . .
C5 C 0.0590(3) 0.3385(5) 0.1003(3) 0.0480(11) Uani 1 1 d . . .
H2 H 0.0155 0.3967 0.0726 0.058 Uiso 1 1 calc R . .
C6 C 0.1451(2) 0.3407(4) 0.0767(3) 0.0361(9) Uani 1 1 d . . .
C7 C 0.1862(3) 0.4361(4) 0.0113(3) 0.0389(9) Uani 1 1 d . . .
C8 C 0.4972(3) 0.4113(5) 0.1174(3) 0.0462(10) Uani 1 1 d . . .
C9 C 0.5187(2) 0.3216(4) 0.0405(3) 0.0398(10) Uani 1 1 d . . .
C10 C 0.5969(3) 0.3187(5) -0.0018(3) 0.0510(12) Uani 1 1 d . . .
H6 H 0.6448 0.3779 0.0156 0.061 Uiso 1 1 calc R . .
C11 C 0.6017(3) 0.2257(5) -0.0703(3) 0.0574(13) Uani 1 1 d . . .
H5 H 0.6538 0.2213 -0.0994 0.069 Uiso 1 1 calc R . .
C12 C 0.5298(3) 0.1380(5) -0.0967(3) 0.0547(12) Uani 1 1 d . . .
H4 H 0.5330 0.0751 -0.1431 0.066 Uiso 1 1 calc R . .
C13 C 0.4538(3) 0.1474(4) -0.0522(3) 0.0427(10) Uani 1 1 d . . .
C14 C 0.3682(3) 0.0621(5) -0.0662(3) 0.0470(11) Uani 1 1 d . . .
C20 C 0.3832(4) 0.3073(8) 0.3793(6) 0.105(3) Uani 1 1 d . . .
H20A H 0.3489 0.2284 0.3546 0.158 Uiso 1 1 calc R . .
H20B H 0.3618 0.3962 0.3538 0.158 Uiso 1 1 calc R . .
H20C H 0.3775 0.3101 0.4404 0.158 Uiso 1 1 calc R . .
C17 C 0.4788(3) 0.2876(6) 0.3621(4) 0.0610(14) Uani 1 1 d . . .
C18 C 0.5438(4) 0.3838(6) 0.3895(4) 0.0746(16) Uani 1 1 d . . .
H18 H 0.5284 0.4652 0.4202 0.089 Uiso 1 1 calc R . .
C19 C 0.6297(4) 0.3626(7) 0.3729(5) 0.086(2) Uani 1 1 d . . .
H19 H 0.6732 0.4279 0.3929 0.103 Uiso 1 1 calc R . .
N3 N 0.6515(4) 0.2492(6) 0.3284(4) 0.0748(15) Uani 1 1 d . . .
C16 C 0.5051(4) 0.1743(7) 0.3130(4) 0.0722(15) Uani 1 1 d . . .
H16 H 0.4628 0.1096 0.2898 0.087 Uiso 1 1 calc R . .
C15 C 0.5925(4) 0.1556(8) 0.2981(4) 0.0796(17) Uani 1 1 d . . .
H15 H 0.6102 0.0766 0.2666 0.095 Uiso 1 1 calc R . .
N1 N 0.2060(2) 0.2548(3) 0.1147(2) 0.0316(7) Uani 1 1 d . . .
N1A N 0.4505(2) 0.2379(3) 0.0141(2) 0.0347(8) Uani 1 1 d . . .
O1 O 0.2684(2) 0.0006(5) 0.2713(3) 0.0902(14) Uani 1 1 d . . .
O2W O 0.3214(3) 0.3043(5) -0.2093(3) 0.0839(12) Uani 1 1 d . . .
O2 O 0.34068(18) 0.1133(3) 0.1713(2) 0.0479(8) Uani 1 1 d . . .
O1W O 0.1951(3) -0.2121(5) -0.1128(3) 0.0836(12) Uani 1 1 d . . .
O3 O 0.1411(2) 0.5297(3) -0.0274(2) 0.0552(8) Uani 1 1 d . . .
O4 O 0.26848(18) 0.4100(3) 0.00166(19) 0.0456(7) Uani 1 1 d . . .
O5 O 0.41649(18) 0.3939(3) 0.13908(19) 0.0473(7) Uani 1 1 d . . .
O6 O 0.5531(2) 0.4912(4) 0.1533(2) 0.0666(10) Uani 1 1 d . . .
O7 O 0.30878(19) 0.0991(3) -0.01516(19) 0.0481(7) Uani 1 1 d . . .
O8 O 0.3606(2) -0.0348(4) -0.1199(2) 0.0652(10) Uani 1 1 d . . .
Co1 Co 0.33374(3) 0.25615(6) 0.07468(4) 0.0421(3) Uani 1 1 d . . .
H3N3 H 0.706(4) 0.228(6) 0.312(4) 0.08(2) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.331(5) . ?
C1 C3 1.365(6) . ?
C1 C2 1.519(6) . ?
C2 O1 1.206(5) . ?
C2 O2 1.287(5) . ?
C3 C4 1.393(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(6) . ?
C4 H1 0.9300 . ?
C5 C6 1.367(5) . ?
C5 H2 0.9300 . ?
C6 N1 1.322(5) . ?
C6 C7 1.510(6) . ?
C7 O3 1.232(5) . ?
C7 O4 1.279(5) . ?
C8 O6 1.226(5) . ?
C8 O5 1.290(5) . ?
C8 C9 1.508(6) . ?
C9 N1A 1.327(5) . ?
C9 C10 1.384(6) . ?
C10 C11 1.375(7) . ?
C10 H6 0.9300 . ?
C11 C12 1.392(7) . ?
C11 H5 0.9300 . ?
C12 C13 1.376(6) . ?
C12 H4 0.9300 . ?
C13 N1A 1.332(5) . ?
C13 C14 1.512(6) . ?
C14 O8 1.226(5) . ?
C14 O7 1.280(5) . ?
C20 C17 1.488(8) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C17 C18 1.370(7) . ?
C17 C16 1.372(8) . ?
C18 C19 1.346(8) . ?
C18 H18 0.9300 . ?
C19 N3 1.312(8) . ?
C19 H19 0.9300 . ?
N3 C15 1.305(8) . ?
N3 H3N3 0.89(6) . ?
C16 C15 1.359(8) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
N1 Co1 2.056(3) . ?
N1A Co1 2.052(3) . ?
O2 Co1 1.998(3) . ?
O4 Co1 2.033(3) . ?
O5 Co1 2.003(3) . ?
O7 Co1 2.034(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C3 120.4(4) . . ?
N1 C1 C2 111.2(3) . . ?
C3 C1 C2 128.4(4) . . ?
O1 C2 O2 125.4(4) . . ?
O1 C2 C1 120.8(4) . . ?
O2 C2 C1 113.7(4) . . ?
C1 C3 C4 118.1(4) . . ?
C1 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H1 119.8 . . ?
C3 C4 H1 119.8 . . ?
C6 C5 C4 118.0(4) . . ?
C6 C5 H2 121.0 . . ?
C4 C5 H2 121.0 . . ?
N1 C6 C5 120.7(4) . . ?
N1 C6 C7 110.6(3) . . ?
C5 C6 C7 128.7(4) . . ?
O3 C7 O4 125.4(4) . . ?
O3 C7 C6 120.4(4) . . ?
O4 C7 C6 114.2(3) . . ?
O6 C8 O5 125.7(4) . . ?
O6 C8 C9 121.1(4) . . ?
O5 C8 C9 113.1(4) . . ?
N1A C9 C10 120.3(4) . . ?
N1A C9 C8 111.4(3) . . ?
C10 C9 C8 128.3(4) . . ?
C11 C10 C9 118.0(4) . . ?
C11 C10 H6 121.0 . . ?
C9 C10 H6 121.0 . . ?
C10 C11 C12 121.0(4) . . ?
C10 C11 H5 119.5 . . ?
C12 C11 H5 119.5 . . ?
C13 C12 C11 118.0(4) . . ?
C13 C12 H4 121.0 . . ?
C11 C12 H4 121.0 . . ?
N1A C13 C12 120.2(4) . . ?
N1A C13 C14 111.4(4) . . ?
C12 C13 C14 128.4(4) . . ?
O8 C14 O7 125.5(4) . . ?
O8 C14 C13 121.4(4) . . ?
O7 C14 C13 113.1(4) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C17 C16 116.4(5) . . ?
C18 C17 C20 122.7(6) . . ?
C16 C17 C20 120.8(6) . . ?
C19 C18 C17 121.2(6) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
N3 C19 C18 119.6(6) . . ?
N3 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C15 N3 C19 122.4(6) . . ?
C15 N3 H3N3 111(4) . . ?
C19 N3 H3N3 127(4) . . ?
C15 C16 C17 120.7(5) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
N3 C15 C16 119.6(6) . . ?
N3 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C6 N1 C1 122.5(3) . . ?
C6 N1 Co1 119.6(3) . . ?
C1 N1 Co1 118.0(3) . . ?
C9 N1A C13 122.6(4) . . ?
C9 N1A Co1 118.4(3) . . ?
C13 N1A Co1 118.9(3) . . ?
C2 O2 Co1 120.3(3) . . ?
C7 O4 Co1 120.1(3) . . ?
C8 O5 Co1 120.8(3) . . ?
C14 O7 Co1 120.8(3) . . ?
O2 Co1 O5 92.82(13) . . ?
O2 Co1 O4 151.97(12) . . ?
O5 Co1 O4 95.17(13) . . ?
O2 Co1 O7 92.15(14) . . ?
O5 Co1 O7 151.51(12) . . ?
O4 Co1 O7 93.48(13) . . ?
O2 Co1 N1A 106.61(12) . . ?
O5 Co1 N1A 76.14(13) . . ?
O4 Co1 N1A 101.38(12) . . ?
O7 Co1 N1A 75.55(13) . . ?
O2 Co1 N1 76.81(12) . . ?
O5 Co1 N1 114.42(12) . . ?
O4 Co1 N1 75.42(12) . . ?
O7 Co1 N1 94.03(12) . . ?
N1A Co1 N1 169.02(13) . . ?

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
N1 C1 C2 O1 178.8(5) . . . . ?
C3 C1 C2 O1 -1.3(8) . . . . ?
N1 C1 C2 O2 -0.9(5) . . . . ?
C3 C1 C2 O2 179.0(4) . . . . ?
N1 C1 C3 C4 -0.4(7) . . . . ?
C2 C1 C3 C4 179.7(4) . . . . ?
C1 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C4 C5 C6 N1 2.0(6) . . . . ?
C4 C5 C6 C7 -175.6(4) . . . . ?
N1 C6 C7 O3 -175.8(4) . . . . ?
C5 C6 C7 O3 1.9(6) . . . . ?
N1 C6 C7 O4 4.0(5) . . . . ?
C5 C6 C7 O4 -178.2(4) . . . . ?
O6 C8 C9 N1A 177.0(4) . . . . ?
O5 C8 C9 N1A -3.1(5) . . . . ?
O6 C8 C9 C10 -3.0(7) . . . . ?
O5 C8 C9 C10 176.9(4) . . . . ?
N1A C9 C10 C11 -0.9(6) . . . . ?
C8 C9 C10 C11 179.0(4) . . . . ?
C9 C10 C11 C12 0.5(7) . . . . ?
C10 C11 C12 C13 0.0(7) . . . . ?
C11 C12 C13 N1A -0.2(6) . . . . ?
C11 C12 C13 C14 -178.2(4) . . . . ?
N1A C13 C14 O8 -174.3(4) . . . . ?
C12 C13 C14 O8 3.9(7) . . . . ?
N1A C13 C14 O7 3.5(5) . . . . ?
C12 C13 C14 O7 -178.3(4) . . . . ?
C16 C17 C18 C19 -3.6(9) . . . . ?
C20 C17 C18 C19 179.9(6) . . . . ?
C17 C18 C19 N3 1.2(10) . . . . ?
C18 C19 N3 C15 0.9(10) . . . . ?
C18 C17 C16 C15 4.1(9) . . . . ?
C20 C17 C16 C15 -179.3(6) . . . . ?
C19 N3 C15 C16 -0.3(9) . . . . ?
C17 C16 C15 N3 -2.3(9) . . . . ?
C5 C6 N1 C1 -2.6(6) . . . . ?
C7 C6 N1 C1 175.4(3) . . . . ?
C5 C6 N1 Co1 177.9(3) . . . . ?
C7 C6 N1 Co1 -4.1(4) . . . . ?
C3 C1 N1 C6 1.8(6) . . . . ?
C2 C1 N1 C6 -178.4(3) . . . . ?
C3 C1 N1 Co1 -178.7(3) . . . . ?
C2 C1 N1 Co1 1.2(4) . . . . ?
C10 C9 N1A C13 0.8(6) . . . . ?
C8 C9 N1A C13 -179.2(3) . . . . ?
C10 C9 N1A Co1 -176.3(3) . . . . ?
C8 C9 N1A Co1 3.7(4) . . . . ?
C12 C13 N1A C9 -0.2(6) . . . . ?
C14 C13 N1A C9 178.1(3) . . . . ?
C12 C13 N1A Co1 176.8(3) . . . . ?
C14 C13 N1A Co1 -4.8(4) . . . . ?
O1 C2 O2 Co1 -179.5(4) . . . . ?
C1 C2 O2 Co1 0.1(5) . . . . ?
O3 C7 O4 Co1 177.6(3) . . . . ?
C6 C7 O4 Co1 -2.2(4) . . . . ?
O6 C8 O5 Co1 -178.9(3) . . . . ?
C9 C8 O5 Co1 1.1(5) . . . . ?
O8 C14 O7 Co1 177.0(3) . . . . ?
C13 C14 O7 Co1 -0.7(5) . . . . ?
C2 O2 Co1 O5 114.8(3) . . . . ?
C2 O2 Co1 O4 8.3(5) . . . . ?
C2 O2 Co1 O7 -93.3(3) . . . . ?
C2 O2 Co1 N1A -168.8(3) . . . . ?
C2 O2 Co1 N1 0.4(3) . . . . ?
C8 O5 Co1 O2 107.0(3) . . . . ?
C8 O5 Co1 O4 -99.9(3) . . . . ?
C8 O5 Co1 O7 7.3(5) . . . . ?
C8 O5 Co1 N1A 0.6(3) . . . . ?
C8 O5 Co1 N1 -176.2(3) . . . . ?
C7 O4 Co1 O2 -7.8(5) . . . . ?
C7 O4 Co1 O5 -113.8(3) . . . . ?
C7 O4 Co1 O7 93.4(3) . . . . ?
C7 O4 Co1 N1A 169.3(3) . . . . ?
C7 O4 Co1 N1 0.1(3) . . . . ?
C14 O7 Co1 O2 -108.0(3) . . . . ?
C14 O7 Co1 O5 -8.0(5) . . . . ?
C14 O7 Co1 O4 99.5(3) . . . . ?
C14 O7 Co1 N1A -1.4(3) . . . . ?
C14 O7 Co1 N1 175.1(3) . . . . ?
C9 N1A Co1 O2 -91.4(3) . . . . ?
C13 N1A Co1 O2 91.5(3) . . . . ?
C9 N1A Co1 O5 -2.6(3) . . . . ?
C13 N1A Co1 O5 -179.7(3) . . . . ?
C9 N1A Co1 O4 90.0(3) . . . . ?
C13 N1A Co1 O4 -87.2(3) . . . . ?
C9 N1A Co1 O7 -179.3(3) . . . . ?
C13 N1A Co1 O7 3.5(3) . . . . ?
C9 N1A Co1 N1 162.0(6) . . . . ?
C13 N1A Co1 N1 -15.2(8) . . . . ?
C6 N1 Co1 O2 178.7(3) . . . . ?
C1 N1 Co1 O2 -0.9(3) . . . . ?
C6 N1 Co1 O5 91.6(3) . . . . ?
C1 N1 Co1 O5 -88.0(3) . . . . ?
C6 N1 Co1 O4 2.5(3) . . . . ?
C1 N1 Co1 O4 -177.1(3) . . . . ?
C6 N1 Co1 O7 -90.1(3) . . . . ?
C1 N1 Co1 O7 90.4(3) . . . . ?
C6 N1 Co1 N1A -71.9(7) . . . . ?
C1 N1 Co1 N1A 108.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.097

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1440315'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Fe N3 O10'
_chemical_formula_weight         512.19

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   15.0469(3)
_cell_length_b                   9.2868(2)
_cell_length_c                   15.5703(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.0110(10)
_cell_angle_gamma                90.00
_cell_volume                     2170.43(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1044
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.834
_exptl_absorpt_process_details   'Face indexing'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26129
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4031
_reflns_number_gt                3300
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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+0.5371P] 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         4031
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.019
_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
Fe1 Fe 0.33377(2) 0.24378(4) 0.07470(2) 0.03679(16) Uani 1 1 d . . .
C2 C 0.14540(14) 0.1584(2) 0.07684(14) 0.0341(5) Uani 1 1 d . . .
C1 C 0.18607(15) 0.0636(3) 0.01076(14) 0.0368(5) Uani 1 1 d . . .
C3 C 0.05874(15) 0.1610(3) 0.10016(17) 0.0453(6) Uani 1 1 d . . .
H3 H 0.0152 0.1030 0.0725 0.054 Uiso 1 1 calc R . .
C6 C 0.18829(15) 0.3326(3) 0.17910(15) 0.0384(5) Uani 1 1 d . . .
C7 C 0.27082(18) 0.4157(3) 0.21196(17) 0.0490(6) Uani 1 1 d . . .
C5 C 0.10365(16) 0.3401(3) 0.20788(17) 0.0493(6) Uani 1 1 d . . .
H5 H 0.0908 0.4006 0.2530 0.059 Uiso 1 1 calc R . .
C4 C 0.03841(19) 0.2534(3) 0.1667(2) 0.0533(8) Uani 1 1 d . . .
H4 H -0.0196 0.2570 0.1837 0.064 Uiso 1 1 calc R . .
C9 C 0.51881(14) 0.1787(3) 0.04028(15) 0.0385(5) Uani 1 1 d . . .
C8 C 0.49721(16) 0.0888(3) 0.11738(16) 0.0430(6) Uani 1 1 d . . .
C14 C 0.36824(17) 0.4386(3) -0.06605(16) 0.0450(6) Uani 1 1 d . . .
C13 C 0.45378(16) 0.3533(3) -0.05246(15) 0.0420(6) Uani 1 1 d . . .
C10 C 0.59681(16) 0.1819(3) -0.00188(18) 0.0492(6) Uani 1 1 d . . .
H10 H 0.6446 0.1230 0.0158 0.059 Uiso 1 1 calc R . .
C12 C 0.52983(18) 0.3626(3) -0.09716(16) 0.0525(7) Uani 1 1 d . . .
H12 H 0.5328 0.4255 -0.1433 0.063 Uiso 1 1 calc R . .
C11 C 0.6019(2) 0.2748(3) -0.0709(2) 0.0575(8) Uani 1 1 d . . .
H11 H 0.6538 0.2787 -0.1000 0.069 Uiso 1 1 calc R . .
O7 O 0.41692(11) 0.10567(19) 0.13896(11) 0.0463(4) Uani 1 1 d . . .
O1 O 0.26829(11) 0.09025(19) 0.00168(11) 0.0453(4) Uani 1 1 d . . .
O3 O 0.34049(11) 0.3861(2) 0.17159(11) 0.0473(4) Uani 1 1 d . . .
O5 O 0.30893(11) 0.4014(2) -0.01509(11) 0.0486(4) Uani 1 1 d . . .
O2 O 0.14114(12) -0.0299(2) -0.02767(12) 0.0547(5) Uani 1 1 d . . .
O6 O 0.36028(15) 0.5357(2) -0.11973(13) 0.0643(6) Uani 1 1 d . . .
O8 O 0.55288(13) 0.0097(2) 0.15345(14) 0.0662(6) Uani 1 1 d . . .
O4 O 0.26814(15) 0.4997(3) 0.27160(17) 0.0885(9) Uani 1 1 d . . .
N1 N 0.20637(13) 0.24498(17) 0.11499(13) 0.0307(4) Uani 1 1 d . . .
N2 N 0.45039(14) 0.26203(19) 0.01363(14) 0.0356(5) Uani 1 1 d . . .
C18 C 0.4565(2) 0.8846(4) 0.6094(2) 0.0736(9) Uani 1 1 d . . .
H18 H 0.4717 0.9647 0.5777 0.088 Uiso 1 1 calc R . .
C20 C 0.6171(3) 0.8075(5) 0.6205(3) 0.0998(14) Uani 1 1 d . . .
H20A H 0.6494 0.8484 0.6699 0.150 Uiso 1 1 calc R . .
H20B H 0.6208 0.8707 0.5721 0.150 Uiso 1 1 calc R . .
H20C H 0.6424 0.7157 0.6076 0.150 Uiso 1 1 calc R . .
C15 C 0.4956(2) 0.6734(4) 0.6861(2) 0.0706(9) Uani 1 1 d . . .
H15 H 0.5378 0.6070 0.7076 0.085 Uiso 1 1 calc R . .
C19 C 0.5216(2) 0.7882(4) 0.6389(2) 0.0593(8) Uani 1 1 d . . .
C17 C 0.3700(2) 0.8626(4) 0.6268(3) 0.0833(11) Uani 1 1 d . . .
H17 H 0.3263 0.9277 0.6070 0.100 Uiso 1 1 calc R . .
C16 C 0.4077(3) 0.6557(4) 0.7019(2) 0.0786(10) Uani 1 1 d . . .
H16 H 0.3903 0.5775 0.7341 0.094 Uiso 1 1 calc R . .
N3 N 0.3484(2) 0.7490(3) 0.6716(2) 0.0754(9) Uani 1 1 d . . .
H3A H 0.2934 0.7358 0.6813 0.091 Uiso 1 1 calc R . .
O9 O 0.19527(17) 0.7115(3) 0.88689(17) 0.0816(7) Uani 1 1 d . . .
O10 O 0.17884(16) 0.6959(3) 0.70892(17) 0.0833(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O3 2.0030(17) . ?
Fe1 O7 2.0092(17) . ?
Fe1 O1 2.0347(17) . ?
Fe1 O5 2.0403(18) . ?
Fe1 N1 2.058(2) . ?
Fe1 N2 2.061(2) . ?
C2 N1 1.328(3) . ?
C2 C3 1.378(3) . ?
C2 C1 1.515(3) . ?
C1 O2 1.230(3) . ?
C1 O1 1.279(3) . ?
C3 C4 1.395(4) . ?
C6 N1 1.331(3) . ?
C6 C5 1.381(3) . ?
C6 C7 1.520(3) . ?
C7 O4 1.215(3) . ?
C7 O3 1.289(3) . ?
C5 C4 1.391(4) . ?
C9 N2 1.331(3) . ?
C9 C10 1.385(3) . ?
C9 C8 1.516(4) . ?
C8 O8 1.221(3) . ?
C8 O7 1.286(3) . ?
C14 O6 1.230(3) . ?
C14 O5 1.282(3) . ?
C14 C13 1.514(4) . ?
C13 N2 1.337(3) . ?
C13 C12 1.383(3) . ?
C10 C11 1.384(4) . ?
C12 C11 1.395(4) . ?
C18 C17 1.363(5) . ?
C18 C19 1.382(5) . ?
C20 C19 1.496(5) . ?
C15 C19 1.367(5) . ?
C15 C16 1.372(5) . ?
C17 N3 1.319(5) . ?
C16 N3 1.308(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
O3 Fe1 O7 92.83(8) . . ?
O3 Fe1 O1 151.68(7) . . ?
O7 Fe1 O1 95.24(8) . . ?
O3 Fe1 O5 92.29(8) . . ?
O7 Fe1 O5 151.28(7) . . ?
O1 Fe1 O5 93.52(8) . . ?
O3 Fe1 N1 76.46(7) . . ?
O7 Fe1 N1 114.36(7) . . ?
O1 Fe1 N1 75.48(7) . . ?
O5 Fe1 N1 94.31(7) . . ?
O3 Fe1 N2 107.07(7) . . ?
O7 Fe1 N2 76.20(7) . . ?
O1 Fe1 N2 101.21(7) . . ?
O5 Fe1 N2 75.28(7) . . ?
N1 Fe1 N2 168.99(8) . . ?
N1 C2 C3 120.6(2) . . ?
N1 C2 C1 110.87(18) . . ?
C3 C2 C1 128.6(2) . . ?
O2 C1 O1 125.9(2) . . ?
O2 C1 C2 120.4(2) . . ?
O1 C1 C2 113.72(19) . . ?
C2 C3 C4 117.8(2) . . ?
N1 C6 C5 121.0(2) . . ?
N1 C6 C7 111.0(2) . . ?
C5 C6 C7 128.0(2) . . ?
O4 C7 O3 125.5(3) . . ?
O4 C7 C6 120.9(2) . . ?
O3 C7 C6 113.6(2) . . ?
C6 C5 C4 117.3(2) . . ?
C5 C4 C3 120.9(2) . . ?
N2 C9 C10 120.2(2) . . ?
N2 C9 C8 111.30(19) . . ?
C10 C9 C8 128.5(2) . . ?
O8 C8 O7 125.4(2) . . ?
O8 C8 C9 121.2(2) . . ?
O7 C8 C9 113.4(2) . . ?
O6 C14 O5 125.4(3) . . ?
O6 C14 C13 121.4(2) . . ?
O5 C14 C13 113.2(2) . . ?
N2 C13 C12 120.3(2) . . ?
N2 C13 C14 111.2(2) . . ?
C12 C13 C14 128.5(2) . . ?
C11 C10 C9 118.4(3) . . ?
C13 C12 C11 118.0(3) . . ?
C10 C11 C12 120.5(2) . . ?
C8 O7 Fe1 120.76(16) . . ?
C1 O1 Fe1 120.53(14) . . ?
C7 O3 Fe1 120.53(16) . . ?
C14 O5 Fe1 121.02(16) . . ?
C2 N1 C6 122.3(2) . . ?
C2 N1 Fe1 119.29(15) . . ?
C6 N1 Fe1 118.40(15) . . ?
C9 N2 C13 122.6(2) . . ?
C9 N2 Fe1 118.27(16) . . ?
C13 N2 Fe1 119.14(17) . . ?
C17 C18 C19 120.1(4) . . ?
C19 C15 C16 120.3(3) . . ?
C15 C19 C18 117.5(3) . . ?
C15 C19 C20 120.7(3) . . ?
C18 C19 C20 121.8(4) . . ?
N3 C17 C18 120.0(3) . . ?
N3 C16 C15 119.9(3) . . ?
C16 N3 C17 122.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.109
