# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_md_21_0m
_database_code_depnum_ccdc_archive 'CCDC 1421271'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 Co N7 O5 S2'
_chemical_formula_weight         622.54

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'
S S 0.1246 0.1234 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   10.692(2)
_cell_length_b                   11.464(2)
_cell_length_c                   24.031(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2945.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6073
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.99

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1276
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8307
_exptl_absorpt_correction_T_max  0.9200
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13288
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5758
_reflns_number_gt                5193
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 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)+(0.0645P)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     SHELXL
_refine_ls_extinction_coef       0.0143(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(14)
_refine_ls_number_reflns         5758
_refine_ls_number_parameters     370
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.002
_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
O3 O 0.2894(3) 0.1498(3) 0.45388(11) 0.0760(9) Uani 1 1 d . . .
O4 O 0.3877(5) 0.3739(3) 0.30091(16) 0.1081(13) Uani 1 1 d . . .
O6 O 0.2086(4) 0.3209(3) 0.37884(17) 0.0969(11) Uani 1 1 d . . .
H5A H -0.083(3) 0.662(3) 0.6925(14) 0.040(9) Uiso 1 1 d . . .
C1 C 0.3824(3) 0.4814(3) 0.59594(12) 0.0374(6) Uani 1 1 d . . .
C2 C 0.4920(3) 0.5479(3) 0.59386(16) 0.0512(9) Uani 1 1 d . . .
H2 H 0.5649 0.5181 0.5782 0.061 Uiso 1 1 calc R . .
C3 C 0.4885(4) 0.6600(3) 0.61590(19) 0.0617(11) Uani 1 1 d . . .
H3 H 0.5602 0.7060 0.6154 0.074 Uiso 1 1 calc R . .
C4 C 0.3791(4) 0.7035(3) 0.63853(16) 0.0556(9) Uani 1 1 d . . .
H4 H 0.3762 0.7790 0.6527 0.067 Uiso 1 1 calc R . .
C5 C 0.2734(3) 0.6327(3) 0.63985(12) 0.0390(7) Uani 1 1 d . . .
C6 C 0.1504(3) 0.6658(3) 0.66357(13) 0.0399(8) Uani 1 1 d . . .
C7 C 0.3710(3) 0.3602(3) 0.57487(12) 0.0388(7) Uani 1 1 d . . .
C8 C 0.1297(4) 0.7849(3) 0.68758(16) 0.0569(9) Uani 1 1 d . . .
H8A H 0.0454 0.7909 0.7010 0.085 Uiso 1 1 calc R . .
H8B H 0.1436 0.8427 0.6593 0.085 Uiso 1 1 calc R . .
H8C H 0.1869 0.7974 0.7178 0.085 Uiso 1 1 calc R . .
C9 C 0.4768(3) 0.2984(3) 0.54633(18) 0.0590(10) Uani 1 1 d . . .
H9A H 0.4506 0.2212 0.5360 0.088 Uiso 1 1 calc R . .
H9B H 0.5470 0.2934 0.5711 0.088 Uiso 1 1 calc R . .
H9C H 0.5005 0.3409 0.5136 0.088 Uiso 1 1 calc R . .
C10 C 0.1281(3) 0.1579(2) 0.58521(12) 0.0355(6) Uani 1 1 d D . .
C11 C 0.0981(3) 0.0361(3) 0.56772(12) 0.0408(7) Uani 1 1 d . . .
C12 C -0.0275(4) 0.0005(3) 0.56692(14) 0.0506(9) Uani 1 1 d . . .
H12 H -0.0898 0.0528 0.5773 0.061 Uiso 1 1 calc R . .
C13 C -0.0598(5) -0.1114(3) 0.55085(16) 0.0651(11) Uani 1 1 d . . .
H13 H -0.1435 -0.1336 0.5503 0.078 Uiso 1 1 calc R . .
C14 C 0.0314(5) -0.1904(4) 0.53568(17) 0.0723(13) Uani 1 1 d . . .
H14 H 0.0099 -0.2658 0.5251 0.087 Uiso 1 1 calc R . .
C15 C 0.1571(5) -0.1554(3) 0.53646(17) 0.0696(13) Uani 1 1 d . . .
H15 H 0.2190 -0.2081 0.5262 0.083 Uiso 1 1 calc R . .
C16 C 0.1903(4) -0.0437(3) 0.55223(15) 0.0529(9) Uani 1 1 d . . .
H16 H 0.2740 -0.0218 0.5525 0.063 Uiso 1 1 calc R . .
C17 C -0.1173(3) 0.4940(2) 0.68458(11) 0.0350(6) Uani 1 1 d . . .
C18 C -0.2391(3) 0.4983(3) 0.71556(12) 0.0379(7) Uani 1 1 d . . .
C19 C -0.2544(4) 0.5733(3) 0.76111(15) 0.0535(9) Uani 1 1 d . . .
H19 H -0.1905 0.6236 0.7717 0.064 Uiso 1 1 calc R . .
C20 C -0.3666(5) 0.5712(4) 0.79019(19) 0.0726(12) Uani 1 1 d . . .
H20 H -0.3779 0.6206 0.8205 0.087 Uiso 1 1 calc R . .
C21 C -0.4610(4) 0.4970(4) 0.77470(18) 0.0716(12) Uani 1 1 d . . .
H21 H -0.5359 0.4971 0.7943 0.086 Uiso 1 1 calc R . .
C22 C -0.4456(4) 0.4213(4) 0.72978(17) 0.0660(11) Uani 1 1 d . . .
H22 H -0.5097 0.3708 0.7195 0.079 Uiso 1 1 calc R . .
C23 C -0.3332(3) 0.4221(3) 0.70046(14) 0.0497(8) Uani 1 1 d . . .
H23 H -0.3216 0.3714 0.6707 0.060 Uiso 1 1 calc R . .
C25 C 0.2008(3) 0.3569(3) 0.75431(13) 0.0394(7) Uani 1 1 d . . .
C26 C 0.0540(3) 0.4909(3) 0.50340(13) 0.0386(7) Uani 1 1 d . . .
N1 N 0.2769(2) 0.5234(2) 0.61886(10) 0.0357(6) Uani 1 1 d . . .
N2 N 0.2640(2) 0.3145(2) 0.58460(10) 0.0352(6) Uani 1 1 d . . .
N3 N 0.2383(2) 0.2024(2) 0.56706(11) 0.0374(6) Uani 1 1 d D . .
N4 N 0.0706(2) 0.5821(2) 0.66189(10) 0.0374(6) Uani 1 1 d . . .
N5 N -0.0474(3) 0.5941(2) 0.68384(11) 0.0417(6) Uani 1 1 d . . .
N6 N 0.1801(3) 0.3617(2) 0.70684(11) 0.0454(6) Uani 1 1 d . . .
N7 N 0.0468(3) 0.4560(2) 0.54875(11) 0.0444(6) Uani 1 1 d . . .
O1 O 0.0584(2) 0.21645(19) 0.61565(9) 0.0445(6) Uani 1 1 d . . .
O2 O -0.0786(2) 0.40397(19) 0.66238(9) 0.0416(5) Uani 1 1 d . . .
S1 S 0.06071(13) 0.54185(9) 0.43993(4) 0.0659(3) Uani 1 1 d . . .
S2 S 0.22756(11) 0.34815(10) 0.82140(4) 0.0603(3) Uani 1 1 d . . .
Co1 Co 0.11517(4) 0.40831(3) 0.628385(15) 0.03175(13) Uani 1 1 d . . .
H3A H 0.278(4) 0.167(4) 0.5388(15) 0.099(17) 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
C1 N1 1.344(4) . ?
C1 C2 1.400(5) . ?
C1 C7 1.484(4) . ?
C2 C3 1.390(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.351(4) . ?
C5 C6 1.483(5) . ?
C6 N4 1.285(4) . ?
C6 C8 1.498(5) . ?
C7 N2 1.280(4) . ?
C7 C9 1.501(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O1 1.242(4) . ?
C10 N3 1.356(4) . ?
C10 C11 1.493(4) . ?
C11 C16 1.396(5) . ?
C11 C12 1.403(5) . ?
C12 C13 1.384(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.402(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O2 1.233(4) . ?
C17 N5 1.369(4) . ?
C17 C18 1.501(5) . ?
C18 C23 1.381(5) . ?
C18 C19 1.402(5) . ?
C19 C20 1.389(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.393(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 N6 1.163(4) . ?
C25 S2 1.641(3) . ?
C26 N7 1.164(4) . ?
C26 S1 1.635(3) . ?
N1 Co1 2.187(2) . ?
N2 N3 1.380(4) . ?
N2 Co1 2.190(3) . ?
N3 H3A 0.896(19) . ?
N4 N5 1.374(4) . ?
N4 Co1 2.200(3) . ?
N5 H5A 0.89(4) . ?
N6 Co1 2.079(3) . ?
N7 Co1 2.120(3) . ?
O1 Co1 2.302(2) . ?
O2 Co1 2.228(2) . ?

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 C2 121.5(3) . . ?
N1 C1 C7 114.0(3) . . ?
C2 C1 C7 124.5(3) . . ?
C3 C2 C1 117.9(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 120.7(3) . . ?
N1 C5 C6 113.9(3) . . ?
C4 C5 C6 125.4(3) . . ?
N4 C6 C5 112.7(3) . . ?
N4 C6 C8 126.5(3) . . ?
C5 C6 C8 120.8(3) . . ?
N2 C7 C1 113.2(3) . . ?
N2 C7 C9 124.3(3) . . ?
C1 C7 C9 122.5(3) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 N3 120.5(3) . . ?
O1 C10 C11 122.8(3) . . ?
N3 C10 C11 116.7(3) . . ?
C16 C11 C12 118.8(3) . . ?
C16 C11 C10 122.4(3) . . ?
C12 C11 C10 118.8(3) . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.4(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 119.9(4) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
O2 C17 N5 120.8(3) . . ?
O2 C17 C18 122.2(3) . . ?
N5 C17 C18 116.9(3) . . ?
C23 C18 C19 120.5(3) . . ?
C23 C18 C17 118.8(3) . . ?
C19 C18 C17 120.6(3) . . ?
C20 C19 C18 118.9(4) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 120.6(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.3(4) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C18 C23 C22 120.0(4) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
N6 C25 S2 178.8(3) . . ?
N7 C26 S1 178.6(3) . . ?
C1 N1 C5 120.5(3) . . ?
C1 N1 Co1 119.33(19) . . ?
C5 N1 Co1 119.9(2) . . ?
C7 N2 N3 120.2(3) . . ?
C7 N2 Co1 122.4(2) . . ?
N3 N2 Co1 117.36(18) . . ?
C10 N3 N2 115.2(2) . . ?
C10 N3 H3A 119(3) . . ?
N2 N3 H3A 124(3) . . ?
C6 N4 N5 121.5(3) . . ?
C6 N4 Co1 123.0(2) . . ?
N5 N4 Co1 115.5(2) . . ?
C17 N5 N4 115.0(3) . . ?
C17 N5 H5A 120(2) . . ?
N4 N5 H5A 125(2) . . ?
C25 N6 Co1 164.8(3) . . ?
C26 N7 Co1 155.7(3) . . ?
C10 O1 Co1 115.9(2) . . ?
C17 O2 Co1 116.8(2) . . ?
N6 Co1 N7 179.33(12) . . ?
N6 Co1 N1 89.20(10) . . ?
N7 Co1 N1 91.29(10) . . ?
N6 Co1 N2 93.84(11) . . ?
N7 Co1 N2 86.75(10) . . ?
N1 Co1 N2 70.83(9) . . ?
N6 Co1 N4 88.45(10) . . ?
N7 Co1 N4 91.28(10) . . ?
N1 Co1 N4 70.33(10) . . ?
N2 Co1 N4 141.05(9) . . ?
N6 Co1 O2 88.40(10) . . ?
N7 Co1 O2 90.93(10) . . ?
N1 Co1 O2 141.92(9) . . ?
N2 Co1 O2 147.24(9) . . ?
N4 Co1 O2 71.62(9) . . ?
N6 Co1 O1 87.88(10) . . ?
N7 Co1 O1 92.03(10) . . ?
N1 Co1 O1 140.44(9) . . ?
N2 Co1 O1 70.03(9) . . ?
N4 Co1 O1 148.90(9) . . ?
O2 Co1 O1 77.41(8) . . ?

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 C3 -0.6(5) . . . . ?
C7 C1 C2 C3 -179.3(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C3 C4 C5 N1 -0.7(5) . . . . ?
C3 C4 C5 C6 178.8(3) . . . . ?
N1 C5 C6 N4 2.8(4) . . . . ?
C4 C5 C6 N4 -176.7(3) . . . . ?
N1 C5 C6 C8 -178.8(3) . . . . ?
C4 C5 C6 C8 1.7(5) . . . . ?
N1 C1 C7 N2 -3.2(4) . . . . ?
C2 C1 C7 N2 175.7(3) . . . . ?
N1 C1 C7 C9 178.2(3) . . . . ?
C2 C1 C7 C9 -3.0(5) . . . . ?
O1 C10 C11 C16 -155.4(3) . . . . ?
N3 C10 C11 C16 23.3(4) . . . . ?
O1 C10 C11 C12 24.4(5) . . . . ?
N3 C10 C11 C12 -156.8(3) . . . . ?
C16 C11 C12 C13 -0.3(5) . . . . ?
C10 C11 C12 C13 179.8(3) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C14 C15 C16 C11 0.0(6) . . . . ?
C12 C11 C16 C15 0.1(5) . . . . ?
C10 C11 C16 C15 179.9(3) . . . . ?
O2 C17 C18 C23 -28.0(5) . . . . ?
N5 C17 C18 C23 154.6(3) . . . . ?
O2 C17 C18 C19 148.2(3) . . . . ?
N5 C17 C18 C19 -29.1(4) . . . . ?
C23 C18 C19 C20 -1.1(5) . . . . ?
C17 C18 C19 C20 -177.3(3) . . . . ?
C18 C19 C20 C21 0.1(7) . . . . ?
C19 C20 C21 C22 0.6(7) . . . . ?
C20 C21 C22 C23 -0.3(7) . . . . ?
C19 C18 C23 C22 1.5(5) . . . . ?
C17 C18 C23 C22 177.7(3) . . . . ?
C21 C22 C23 C18 -0.7(6) . . . . ?
C2 C1 N1 C5 1.1(4) . . . . ?
C7 C1 N1 C5 180.0(3) . . . . ?
C2 C1 N1 Co1 -173.7(2) . . . . ?
C7 C1 N1 Co1 5.1(3) . . . . ?
C4 C5 N1 C1 -0.5(4) . . . . ?
C6 C5 N1 C1 180.0(3) . . . . ?
C4 C5 N1 Co1 174.3(2) . . . . ?
C6 C5 N1 Co1 -5.3(3) . . . . ?
C1 C7 N2 N3 179.3(2) . . . . ?
C9 C7 N2 N3 -2.1(5) . . . . ?
C1 C7 N2 Co1 -0.2(3) . . . . ?
C9 C7 N2 Co1 178.4(3) . . . . ?
O1 C10 N3 N2 -0.4(4) . . . . ?
C11 C10 N3 N2 -179.1(2) . . . . ?
C7 N2 N3 C10 172.5(3) . . . . ?
Co1 N2 N3 C10 -7.9(3) . . . . ?
C5 C6 N4 N5 177.4(3) . . . . ?
C8 C6 N4 N5 -0.9(5) . . . . ?
C5 C6 N4 Co1 0.9(4) . . . . ?
C8 C6 N4 Co1 -177.4(3) . . . . ?
O2 C17 N5 N4 -6.1(4) . . . . ?
C18 C17 N5 N4 171.3(2) . . . . ?
C6 N4 N5 C17 -173.1(3) . . . . ?
Co1 N4 N5 C17 3.7(3) . . . . ?
S2 C25 N6 Co1 93(17) . . . . ?
S1 C26 N7 Co1 -138(12) . . . . ?
N3 C10 O1 Co1 8.0(4) . . . . ?
C11 C10 O1 Co1 -173.3(2) . . . . ?
N5 C17 O2 Co1 5.3(4) . . . . ?
C18 C17 O2 Co1 -171.9(2) . . . . ?
C25 N6 Co1 N7 -48(10) . . . . ?
C25 N6 Co1 N1 88.8(10) . . . . ?
C25 N6 Co1 N2 159.5(10) . . . . ?
C25 N6 Co1 N4 18.4(10) . . . . ?
C25 N6 Co1 O2 -53.2(10) . . . . ?
C25 N6 Co1 O1 -130.7(10) . . . . ?
C26 N7 Co1 N6 160(10) . . . . ?
C26 N7 Co1 N1 23.1(6) . . . . ?
C26 N7 Co1 N2 -47.6(6) . . . . ?
C26 N7 Co1 N4 93.5(6) . . . . ?
C26 N7 Co1 O2 165.1(6) . . . . ?
C26 N7 Co1 O1 -117.4(6) . . . . ?
C1 N1 Co1 N6 90.4(2) . . . . ?
C5 N1 Co1 N6 -84.4(2) . . . . ?
C1 N1 Co1 N7 -90.0(2) . . . . ?
C5 N1 Co1 N7 95.1(2) . . . . ?
C1 N1 Co1 N2 -3.9(2) . . . . ?
C5 N1 Co1 N2 -178.8(2) . . . . ?
C1 N1 Co1 N4 179.1(2) . . . . ?
C5 N1 Co1 N4 4.2(2) . . . . ?
C1 N1 Co1 O2 176.82(18) . . . . ?
C5 N1 Co1 O2 2.0(3) . . . . ?
C1 N1 Co1 O1 4.7(3) . . . . ?
C5 N1 Co1 O1 -170.13(19) . . . . ?
C7 N2 Co1 N6 -85.7(2) . . . . ?
N3 N2 Co1 N6 94.8(2) . . . . ?
C7 N2 Co1 N7 94.6(2) . . . . ?
N3 N2 Co1 N7 -84.9(2) . . . . ?
C7 N2 Co1 N1 2.1(2) . . . . ?
N3 N2 Co1 N1 -177.4(2) . . . . ?
C7 N2 Co1 N4 6.6(3) . . . . ?
N3 N2 Co1 N4 -172.95(18) . . . . ?
C7 N2 Co1 O2 -178.7(2) . . . . ?
N3 N2 Co1 O2 1.7(3) . . . . ?
C7 N2 Co1 O1 -172.0(3) . . . . ?
N3 N2 Co1 O1 8.41(19) . . . . ?
C6 N4 Co1 N6 87.0(2) . . . . ?
N5 N4 Co1 N6 -89.7(2) . . . . ?
C6 N4 Co1 N7 -93.6(2) . . . . ?
N5 N4 Co1 N7 89.7(2) . . . . ?
C6 N4 Co1 N1 -2.7(2) . . . . ?
N5 N4 Co1 N1 -179.4(2) . . . . ?
C6 N4 Co1 N2 -7.2(3) . . . . ?
N5 N4 Co1 N2 176.08(18) . . . . ?
C6 N4 Co1 O2 175.9(3) . . . . ?
N5 N4 Co1 O2 -0.89(18) . . . . ?
C6 N4 Co1 O1 170.4(2) . . . . ?
N5 N4 Co1 O1 -6.4(3) . . . . ?
C17 O2 Co1 N6 86.6(2) . . . . ?
C17 O2 Co1 N7 -93.3(2) . . . . ?
C17 O2 Co1 N1 -0.1(3) . . . . ?
C17 O2 Co1 N2 -178.8(2) . . . . ?
C17 O2 Co1 N4 -2.3(2) . . . . ?
C17 O2 Co1 O1 174.8(2) . . . . ?
C10 O1 Co1 N6 -103.6(2) . . . . ?
C10 O1 Co1 N7 77.1(2) . . . . ?
C10 O1 Co1 N1 -17.4(3) . . . . ?
C10 O1 Co1 N2 -8.7(2) . . . . ?
C10 O1 Co1 N4 172.9(2) . . . . ?
C10 O1 Co1 O2 167.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.134
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_cmc21
_database_code_depnum_ccdc_archive 'CCDC 1421272'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 Co N5 O4'
_chemical_formula_weight         490.38

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Cmc2(1)

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

_cell_length_a                   26.0390(11)
_cell_length_b                   11.4044(5)
_cell_length_c                   7.3288(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2176.35(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1765
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      24.71

_exptl_crystal_description       Needle
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1012
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7771
_exptl_absorpt_correction_T_max  0.9519
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4585
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         26.10
_reflns_number_total             1815
_reflns_number_gt                1631
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 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)+(0.0690P)²+0.1598P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_number_reflns         1815
_refine_ls_number_parameters     162
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_restrained_S_all      1.209
_refine_ls_shift/su_max          0.208
_refine_ls_shift/su_mean         0.001

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 1.0000 0.15509(5) 0.04478(9) 0.0118(2) Uani 1 2 d S . .
C1 C 0.86716(14) -0.1749(3) 0.0491(10) 0.0212(9) Uani 1 1 d . . .
H1 H 0.8981 -0.1946 -0.0060 0.025 Uiso 1 1 calc R . .
C7 C 0.89735(14) 0.0328(3) 0.0743(6) 0.0124(10) Uani 1 1 d . . .
C6 C 0.85840(15) -0.0608(4) 0.1063(6) 0.0180(11) Uani 1 1 d . . .
C5 C 0.81233(16) -0.0324(4) 0.1907(7) 0.0199(10) Uani 1 1 d . . .
H5 H 0.8063 0.0443 0.2281 0.024 Uiso 1 1 calc R . .
C2 C 0.82959(17) -0.2597(4) 0.0743(10) 0.0306(15) Uani 1 1 d . . .
H2 H 0.8353 -0.3361 0.0348 0.037 Uiso 1 1 calc R . .
C4 C 0.77535(17) -0.1175(4) 0.2194(8) 0.0281(12) Uani 1 1 d . . .
H4 H 0.7450 -0.0987 0.2796 0.034 Uiso 1 1 calc R . .
C3 C 0.78358(19) -0.2308(4) 0.1585(8) 0.0312(13) Uani 1 1 d . . .
H3 H 0.7583 -0.2875 0.1739 0.037 Uiso 1 1 calc R . .
O1 O 0.94446(8) 0.00281(19) 0.0430(6) 0.0149(6) Uani 1 1 d . . .
N1 N 1.07919(10) 0.2185(2) 0.0577(7) 0.0139(7) Uani 1 1 d . . .
N3 N 1.11958(13) 0.1418(2) 0.0815(6) 0.0159(11) Uani 1 1 d . . .
C9 C 1.09032(13) 0.3289(3) 0.0424(11) 0.0167(8) Uani 1 1 d . . .
N2 N 1.0000 0.3460(3) 0.0339(13) 0.0140(10) Uani 1 2 d S . .
C11 C 1.14307(14) 0.3785(3) 0.0438(11) 0.0297(11) Uani 1 1 d . . .
H11A H 1.1677 0.3159 0.0372 0.045 Uiso 1 1 calc R . .
H11B H 1.1483 0.4220 0.1544 0.045 Uiso 1 1 calc R . .
H11C H 1.1474 0.4296 -0.0592 0.045 Uiso 1 1 calc R . .
C10 C 1.04626(15) 0.5274(3) 0.0168(8) 0.0207(12) Uani 1 1 d . . .
H10 H 1.0774 0.5673 0.0123 0.025 Uiso 1 1 calc R . .
C12 C 1.04497(13) 0.4051(3) 0.0290(8) 0.0152(9) Uani 1 1 d . . .
C13 C 1.0000 0.5879(5) 0.0117(11) 0.0229(18) Uani 1 2 d S . .
H13 H 1.0000 0.6693 0.0047 0.028 Uiso 1 2 calc SR . .
O4 O 1.0000 0.1435(4) 0.3303(8) 0.0144(13) Uani 1 2 d S . .
O3 O 1.0000 0.1512(4) -0.2444(7) 0.0139(13) Uani 1 2 d S . .
H4A H 1.0277(15) 0.116(3) 0.371(6) 0.000(10) 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
Co1 O4 2.097(6) . ?
Co1 O3 2.119(5) . ?
Co1 N2 2.179(4) . ?
Co1 N1 2.187(3) . ?
Co1 N1 2.187(3) 3_755 ?
Co1 O1 2.260(2) . ?
Co1 O1 2.260(2) 3_755 ?
C1 C6 1.387(6) . ?
C1 C2 1.388(5) . ?
C7 O1 1.294(4) . ?
C7 N3 1.320(4) 3_755 ?
C7 C6 1.490(5) . ?
C6 C5 1.388(6) . ?
C5 C4 1.384(6) . ?
C2 C3 1.387(7) . ?
C4 C3 1.384(7) . ?
N1 C9 1.297(4) . ?
N1 N3 1.379(4) . ?
N3 C7 1.320(4) 3_755 ?
C9 C12 1.469(5) . ?
C9 C11 1.485(5) . ?
N2 C12 1.351(4) . ?
N2 C12 1.352(4) 3_755 ?
C10 C13 1.388(5) . ?
C10 C12 1.398(5) . ?
C13 C10 1.388(5) 3_755 ?

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 O3 175.21(13) . . ?
O4 Co1 N2 95.7(3) . . ?
O3 Co1 N2 89.1(3) . . ?
O4 Co1 N1 88.71(15) . . ?
O3 Co1 N1 92.88(15) . . ?
N2 Co1 N1 70.80(8) . . ?
O4 Co1 N1 88.71(15) . 3_755 ?
O3 Co1 N1 92.88(15) . 3_755 ?
N2 Co1 N1 70.80(8) . 3_755 ?
N1 Co1 N1 141.04(15) . 3_755 ?
O4 Co1 O1 87.55(16) . . ?
O3 Co1 O1 88.76(15) . . ?
N2 Co1 O1 140.15(6) . . ?
N1 Co1 O1 149.05(10) . . ?
N1 Co1 O1 69.58(9) 3_755 . ?
O4 Co1 O1 87.55(16) . 3_755 ?
O3 Co1 O1 88.76(15) . 3_755 ?
N2 Co1 O1 140.15(6) . 3_755 ?
N1 Co1 O1 69.58(9) . 3_755 ?
N1 Co1 O1 149.05(10) 3_755 3_755 ?
O1 Co1 O1 79.57(11) . 3_755 ?
C6 C1 C2 119.9(4) . . ?
O1 C7 N3 124.9(3) . 3_755 ?
O1 C7 C6 119.0(3) . . ?
N3 C7 C6 116.1(3) 3_755 . ?
C1 C6 C5 119.7(4) . . ?
C1 C6 C7 120.8(4) . . ?
C5 C6 C7 119.4(4) . . ?
C4 C5 C6 120.4(4) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C4 C5 119.9(5) . . ?
C4 C3 C2 119.9(4) . . ?
C7 O1 Co1 113.8(2) . . ?
C9 N1 N3 117.2(3) . . ?
C9 N1 Co1 121.9(2) . . ?
N3 N1 Co1 121.0(2) . . ?
C7 N3 N1 109.7(3) 3_755 . ?
N1 C9 C12 113.6(3) . . ?
N1 C9 C11 125.1(3) . . ?
C12 C9 C11 121.2(3) . . ?
C12 N2 C12 120.1(4) . 3_755 ?
C12 N2 Co1 119.94(19) . . ?
C12 N2 Co1 119.94(19) 3_755 . ?
C13 C10 C12 118.5(4) . . ?
N2 C12 C10 121.3(3) . . ?
N2 C12 C9 113.6(3) . . ?
C10 C12 C9 125.1(3) . . ?
C10 C13 C10 120.4(5) . 3_755 ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.10
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.138
