# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 1051391'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H28 Co N4 O4'
_chemical_formula_weight         663.57

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   P2(1)/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                   9.3634(15)
_cell_length_b                   21.379(3)
_cell_length_c                   15.200(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.912(2)
_cell_angle_gamma                90.00
_cell_volume                     2977.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4605
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      21.13

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1372
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8438
_exptl_absorpt_correction_T_max  0.9062
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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_reflns_number            28529
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         22.57
_reflns_number_total             3916
_reflns_number_gt                3196
_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    'MERCURY 3.2'
_computing_publication_material  'ORTEP 3V.2'

_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+0.2344P] 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         3916
_refine_ls_number_parameters     426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
Co1 Co 0.23469(4) -0.017847(19) 1.01104(3) 0.0203(2) Uani 1 1 d . . .
N1 N 0.3854(3) 0.04437(12) 1.05563(17) 0.0214(6) Uani 1 1 d . . .
O1 O 0.1537(3) 0.16151(12) 0.66647(17) 0.0415(7) Uani 1 1 d . . .
O4 O 0.2225(3) 0.21669(11) 0.79331(16) 0.0402(7) Uani 1 1 d . . .
C28 C 0.0161(3) 0.03077(15) 0.8497(2) 0.0227(8) Uani 1 1 d . . .
C31 C 0.5068(3) -0.00391(15) 1.1993(2) 0.0203(7) Uani 1 1 d . . .
N3 N 0.0896(3) -0.08152(12) 0.96383(17) 0.0222(6) Uani 1 1 d . . .
C32 C 0.3326(3) 0.12094(15) 0.9328(2) 0.0236(8) Uani 1 1 d . . .
H32 H 0.3670 0.1565 0.9086 0.028 Uiso 1 1 calc R . .
C25 C 0.2064(3) 0.09304(14) 0.8850(2) 0.0236(8) Uani 1 1 d . . .
C19 C 0.4740(3) -0.11658(14) 1.2348(2) 0.0257(8) Uani 1 1 d . . .
H19 H 0.5430 -0.1194 1.2882 0.031 Uiso 1 1 calc R . .
C7 C 0.6157(4) 0.00426(14) 1.2851(2) 0.0229(8) Uani 1 1 d . . .
N2 N 0.3259(3) -0.07503(11) 1.10759(17) 0.0226(6) Uani 1 1 d . . .
C8 C 0.7620(4) 0.01848(14) 1.2867(2) 0.0257(8) Uani 1 1 d . . .
H8 H 0.7933 0.0221 1.2327 0.031 Uiso 1 1 calc R . .
C11 C 0.6711(4) 0.00856(15) 1.4474(2) 0.0309(9) Uani 1 1 d . . .
H11 H 0.6410 0.0051 1.5018 0.037 Uiso 1 1 calc R . .
C12 C 0.5715(4) -0.00101(15) 1.3674(2) 0.0273(8) Uani 1 1 d . . .
H12 H 0.4752 -0.0109 1.3684 0.033 Uiso 1 1 calc R . .
C9 C 0.8612(4) 0.02727(15) 1.3668(2) 0.0287(8) Uani 1 1 d . . .
H9 H 0.9585 0.0359 1.3665 0.034 Uiso 1 1 calc R . .
C1 C 0.1785(4) -0.24076(15) 1.0727(2) 0.0299(8) Uani 1 1 d . . .
C10 C 0.8151(4) 0.02317(15) 1.4470(2) 0.0312(9) Uani 1 1 d . . .
H10 H 0.8808 0.0302 1.5010 0.037 Uiso 1 1 calc R . .
C2 C 0.2340(4) -0.28275(17) 1.0185(2) 0.0427(11) Uani 1 1 d . . .
H2 H 0.2750 -0.2679 0.9718 0.051 Uiso 1 1 calc R . .
C4 C 0.1671(5) -0.36868(18) 1.1024(3) 0.0533(12) Uani 1 1 d . . .
H4 H 0.1648 -0.4115 1.1129 0.064 Uiso 1 1 calc R . .
C6 C 0.1155(4) -0.26399(17) 1.1410(2) 0.0413(10) Uani 1 1 d . . .
H6 H 0.0770 -0.2364 1.1774 0.050 Uiso 1 1 calc R . .
C5 C 0.1092(5) -0.32805(18) 1.1557(3) 0.0488(11) Uani 1 1 d . . .
H5 H 0.0661 -0.3433 1.2014 0.059 Uiso 1 1 calc R . .
C3 C 0.2288(5) -0.34659(18) 1.0334(3) 0.0552(12) Uani 1 1 d . . .
H3 H 0.2667 -0.3744 0.9971 0.066 Uiso 1 1 calc R . .
C26 C 0.1174(3) 0.11767(15) 0.8047(2) 0.0248(8) Uani 1 1 d . . .
C24 C 0.4098(3) 0.09930(14) 1.0137(2) 0.0223(8) Uani 1 1 d . . .
C17 C 0.2973(3) -0.13819(14) 1.1150(2) 0.0227(8) Uani 1 1 d . . .
C21 C 0.4849(3) 0.04458(15) 1.1367(2) 0.0219(8) Uani 1 1 d . . .
C23 C 0.5243(4) 0.13433(15) 1.0698(2) 0.0288(8) Uani 1 1 d . . .
H23 H 0.5614 0.1726 1.0558 0.035 Uiso 1 1 calc R . .
C20 C 0.4356(3) -0.06146(14) 1.1816(2) 0.0209(7) Uani 1 1 d . . .
C13 C -0.0363(3) -0.07409(15) 0.8984(2) 0.0251(8) Uani 1 1 d . . .
C18 C 0.3914(3) -0.16356(16) 1.1928(2) 0.0274(8) Uani 1 1 d . . .
H18 H 0.3950 -0.2051 1.2111 0.033 Uiso 1 1 calc R . .
C14 C -0.1172(4) -0.13137(16) 0.8847(2) 0.0324(9) Uani 1 1 d . . .
H14 H -0.2068 -0.1375 0.8459 0.039 Uiso 1 1 calc R . .
C16 C 0.0881(3) -0.14396(15) 0.9895(2) 0.0251(8) Uani 1 1 d . . .
C22 C 0.5679(3) 0.10176(15) 1.1462(2) 0.0273(8) Uani 1 1 d . . .
H22 H 0.6384 0.1138 1.1957 0.033 Uiso 1 1 calc R . .
C27 C -0.0036(3) 0.07998(14) 0.7839(2) 0.0235(8) Uani 1 1 d . . .
C15 C -0.0395(4) -0.17442(16) 0.9383(2) 0.0312(9) Uani 1 1 d . . .
H15 H -0.0637 -0.2164 0.9419 0.037 Uiso 1 1 calc R . .
C29 C -0.0749(4) -0.02098(15) 0.8478(2) 0.0260(8) Uani 1 1 d . . .
H29 H -0.1668 -0.0196 0.8102 0.031 Uiso 1 1 calc R . .
C30 C 0.1891(3) -0.17183(14) 1.0574(2) 0.0231(8) Uani 1 1 d . . .
N4 N 0.1462(3) 0.03875(12) 0.91120(17) 0.0221(6) Uani 1 1 d . . .
C33 C 0.1629(4) 0.16686(16) 0.7461(3) 0.0299(8) Uani 1 1 d . . .
C34 C -0.1282(4) 0.08546(16) 0.7058(2) 0.0257(8) Uani 1 1 d . . .
O2 O -0.2010(2) 0.04204(12) 0.66962(15) 0.0341(6) Uani 1 1 d . . .
O3 O -0.1487(3) 0.14553(10) 0.67988(15) 0.0346(6) Uani 1 1 d . . .
C36 C -0.2559(4) 0.15824(18) 0.5985(2) 0.0414(10) Uani 1 1 d . . .
H36A H -0.3425 0.1767 0.6134 0.050 Uiso 1 1 calc R . .
H36B H -0.2838 0.1196 0.5659 0.050 Uiso 1 1 calc R . .
C35 C 0.2857(5) 0.26248(17) 0.7405(3) 0.0518(11) Uani 1 1 d . . .
H35A H 0.2087 0.2830 0.6977 0.062 Uiso 1 1 calc R . .
H35B H 0.3500 0.2416 0.7074 0.062 Uiso 1 1 calc R . .
C37 C -0.1922(7) 0.2010(3) 0.5434(4) 0.113(2) Uani 1 1 d . . .
H37A H -0.1623 0.2386 0.5767 0.170 Uiso 1 1 calc R . .
H37B H -0.2632 0.2111 0.4901 0.170 Uiso 1 1 calc R . .
H37C H -0.1090 0.1818 0.5268 0.170 Uiso 1 1 calc R . .
C38 C 0.3682(6) 0.3091(2) 0.8020(4) 0.0885(18) Uani 1 1 d . . .
H38A H 0.3032 0.3308 0.8327 0.133 Uiso 1 1 calc R . .
H38B H 0.4129 0.3385 0.7683 0.133 Uiso 1 1 calc R . .
H38C H 0.4424 0.2884 0.8452 0.133 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 N3 1.952(3) . ?
Co1 N1 1.956(3) . ?
Co1 N2 1.965(3) . ?
Co1 N4 1.984(3) . ?
N1 C24 1.378(4) . ?
N1 C21 1.383(4) . ?
O1 C33 1.201(4) . ?
O4 C33 1.340(4) . ?
O4 C35 1.465(5) . ?
C28 N4 1.384(4) . ?
C28 C29 1.393(5) . ?
C28 C27 1.437(4) . ?
C31 C21 1.394(5) . ?
C31 C20 1.399(4) . ?
C31 C7 1.491(5) . ?
N3 C13 1.386(4) . ?
N3 C16 1.392(4) . ?
C32 C24 1.372(4) . ?
C32 C25 1.388(4) . ?
C25 N4 1.385(4) . ?
C25 C26 1.429(4) . ?
C19 C18 1.345(5) . ?
C19 C20 1.432(4) . ?
C7 C8 1.398(5) . ?
C7 C12 1.401(5) . ?
N2 C17 1.386(4) . ?
N2 C20 1.389(4) . ?
C8 C9 1.384(5) . ?
C11 C10 1.385(5) . ?
C11 C12 1.386(5) . ?
C9 C10 1.377(5) . ?
C1 C6 1.388(5) . ?
C1 C2 1.390(5) . ?
C1 C30 1.498(4) . ?
C2 C3 1.386(5) . ?
C4 C5 1.374(6) . ?
C4 C3 1.380(6) . ?
C6 C5 1.391(5) . ?
C26 C27 1.373(4) . ?
C26 C33 1.495(5) . ?
C24 C23 1.435(4) . ?
C17 C30 1.395(4) . ?
C17 C18 1.427(5) . ?
C21 C22 1.440(4) . ?
C23 C22 1.343(4) . ?
C13 C29 1.377(5) . ?
C13 C14 1.432(5) . ?
C14 C15 1.340(5) . ?
C16 C30 1.383(5) . ?
C16 C15 1.439(5) . ?
C27 C34 1.487(4) . ?
C34 O2 1.214(4) . ?
C34 O3 1.345(4) . ?
O3 C36 1.449(4) . ?
C36 C37 1.449(7) . ?
C35 C38 1.472(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
N3 Co1 N1 177.69(10) . . ?
N3 Co1 N2 90.16(11) . . ?
N1 Co1 N2 89.61(11) . . ?
N3 Co1 N4 89.71(11) . . ?
N1 Co1 N4 90.45(11) . . ?
N2 Co1 N4 178.30(10) . . ?
C24 N1 C21 105.3(2) . . ?
C24 N1 Co1 126.6(2) . . ?
C21 N1 Co1 128.0(2) . . ?
C33 O4 C35 114.1(3) . . ?
N4 C28 C29 124.1(3) . . ?
N4 C28 C27 110.4(3) . . ?
C29 C28 C27 125.2(3) . . ?
C21 C31 C20 121.7(3) . . ?
C21 C31 C7 119.2(3) . . ?
C20 C31 C7 119.0(3) . . ?
C13 N3 C16 104.7(2) . . ?
C13 N3 Co1 127.5(2) . . ?
C16 N3 Co1 127.8(2) . . ?
C24 C32 C25 124.0(3) . . ?
N4 C25 C32 124.2(3) . . ?
N4 C25 C26 110.8(3) . . ?
C32 C25 C26 125.0(3) . . ?
C18 C19 C20 107.1(3) . . ?
C8 C7 C12 118.1(3) . . ?
C8 C7 C31 122.1(3) . . ?
C12 C7 C31 119.8(3) . . ?
C17 N2 C20 105.1(2) . . ?
C17 N2 Co1 127.3(2) . . ?
C20 N2 Co1 127.6(2) . . ?
C9 C8 C7 121.4(3) . . ?
C10 C11 C12 120.6(3) . . ?
C11 C12 C7 120.1(3) . . ?
C10 C9 C8 119.6(3) . . ?
C6 C1 C2 118.8(3) . . ?
C6 C1 C30 121.3(3) . . ?
C2 C1 C30 119.9(3) . . ?
C9 C10 C11 120.1(3) . . ?
C3 C2 C1 120.6(4) . . ?
C5 C4 C3 120.6(4) . . ?
C1 C6 C5 120.7(4) . . ?
C4 C5 C6 119.5(4) . . ?
C4 C3 C2 119.7(4) . . ?
C27 C26 C25 106.8(3) . . ?
C27 C26 C33 126.8(3) . . ?
C25 C26 C33 125.4(3) . . ?
C32 C24 N1 126.5(3) . . ?
C32 C24 C23 123.2(3) . . ?
N1 C24 C23 110.2(3) . . ?
N2 C17 C30 125.4(3) . . ?
N2 C17 C18 110.0(3) . . ?
C30 C17 C18 124.6(3) . . ?
N1 C21 C31 125.7(3) . . ?
N1 C21 C22 110.0(3) . . ?
C31 C21 C22 124.3(3) . . ?
C22 C23 C24 107.4(3) . . ?
N2 C20 C31 125.7(3) . . ?
N2 C20 C19 110.0(3) . . ?
C31 C20 C19 124.1(3) . . ?
C29 C13 N3 125.5(3) . . ?
C29 C13 C14 123.6(3) . . ?
N3 C13 C14 110.6(3) . . ?
C19 C18 C17 107.8(3) . . ?
C15 C14 C13 107.1(3) . . ?
C30 C16 N3 125.3(3) . . ?
C30 C16 C15 124.9(3) . . ?
N3 C16 C15 109.8(3) . . ?
C23 C22 C21 107.0(3) . . ?
C26 C27 C28 106.8(3) . . ?
C26 C27 C34 127.7(3) . . ?
C28 C27 C34 125.4(3) . . ?
C14 C15 C16 107.7(3) . . ?
C13 C29 C28 123.7(3) . . ?
C16 C30 C17 122.9(3) . . ?
C16 C30 C1 118.9(3) . . ?
C17 C30 C1 118.2(3) . . ?
C28 N4 C25 105.2(3) . . ?
C28 N4 Co1 127.7(2) . . ?
C25 N4 Co1 126.9(2) . . ?
O1 C33 O4 123.4(3) . . ?
O1 C33 C26 124.2(3) . . ?
O4 C33 C26 112.3(3) . . ?
O2 C34 O3 124.3(3) . . ?
O2 C34 C27 125.2(3) . . ?
O3 C34 C27 110.5(3) . . ?
C34 O3 C36 117.5(3) . . ?
O3 C36 C37 108.5(4) . . ?
O4 C35 C38 108.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        22.57
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.061
