# 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. 
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#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1436062'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Co N4 O4'
_chemical_formula_weight         387.26

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3256(7)
_cell_length_b                   9.0006(9)
_cell_length_c                   13.7874(14)
_cell_angle_alpha                82.0240(10)
_cell_angle_beta                 78.2670(10)
_cell_angle_gamma                72.3450(10)
_cell_volume                     845.25(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2568
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.44

_exptl_crystal_description       rhombic
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             398
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.044
_shelx_estimated_absorpt_T_min   0.711
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details   '(SADABS;Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart-Apex CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7277
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.514
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3633
_reflns_number_gt                3075
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.2550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3633
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.19568(5) 0.79137(4) 0.76961(2) 0.04257(13) Uani 1 1 d . . . . .
O1 O 0.0167(3) 0.8400(2) 0.89950(13) 0.0511(4) Uani 1 1 d . . . . .
O2 O -0.1155(3) 1.0084(2) 0.78404(15) 0.0612(5) Uani 1 1 d . . . . .
C1 C -0.1277(4) 0.9421(3) 0.86888(19) 0.0446(6) Uani 1 1 d . . . . .
C2 C -0.3202(3) 0.9746(3) 0.93784(18) 0.0409(5) Uani 1 1 d . . . . .
C3 C -0.4896(4) 1.0505(3) 0.90027(18) 0.0434(5) Uani 1 1 d . . . . .
H3A H -0.4827 1.0849 0.8332 0.052 Uiso 1 1 calc R U . . .
C4 C -0.3310(4) 0.9246(3) 1.03818(19) 0.0447(6) Uani 1 1 d . . . . .
H4A H -0.2180 0.8744 1.0640 0.054 Uiso 1 1 calc R U . . .
O3 O 0.0505(4) 0.6791(3) 0.71130(18) 0.0789(7) Uani 1 1 d . . . . .
O4 O 0.3195(4) 0.6577(3) 0.60419(19) 0.0919(8) Uani 1 1 d . . . . .
C5 C 0.1552(5) 0.6376(3) 0.6304(2) 0.0613(8) Uani 1 1 d . . . . .
C6 C 0.0745(4) 0.5643(3) 0.5635(2) 0.0481(6) Uani 1 1 d . . . . .
C7 C -0.1016(4) 0.5331(3) 0.5939(2) 0.0540(6) Uani 1 1 d . . . . .
H7A H -0.1707 0.5549 0.6572 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1769(4) 0.5310(3) 0.4694(2) 0.0558(7) Uani 1 1 d . . . . .
H8A H 0.2965 0.5515 0.4485 0.067 Uiso 1 1 calc R U . . .
N1 N 0.4218(3) 0.6186(2) 0.81903(17) 0.0490(5) Uani 1 1 d . . . . .
C9 C 0.5454(5) 0.6344(3) 0.8703(2) 0.0605(7) Uani 1 1 d . . . . .
H9A H 0.5376 0.7271 0.8956 0.073 Uiso 1 1 calc R U . . .
N2 N 0.6847(4) 0.5002(3) 0.8819(2) 0.0622(7) Uani 1 1 d . . . . .
C10 C 0.6473(5) 0.3934(4) 0.8361(3) 0.0718(9) Uani 1 1 d . . . . .
H10A H 0.7195 0.2892 0.8320 0.086 Uiso 1 1 calc R U . . .
C11 C 0.4856(4) 0.4657(3) 0.7973(3) 0.0628(8) Uani 1 1 d . . . . .
H11A H 0.4265 0.4191 0.7614 0.075 Uiso 1 1 calc R U . . .
C12 C 0.8513(6) 0.4817(5) 0.9314(3) 0.1002(15) Uani 1 1 d . . . . .
H12A H 0.9313 0.3753 0.9306 0.150 Uiso 1 1 calc R U . . .
H12B H 0.9264 0.5499 0.8969 0.150 Uiso 1 1 calc R U . . .
H12C H 0.8050 0.5080 0.9989 0.150 Uiso 1 1 calc R U . . .
N3 N 0.3321(3) 0.9526(2) 0.70081(16) 0.0465(5) Uani 1 1 d . . . . .
C13 C 0.5187(4) 0.9169(3) 0.6635(2) 0.0531(6) Uani 1 1 d . . . . .
H13A H 0.6040 0.8174 0.6710 0.064 Uiso 1 1 calc R U . . .
N4 N 0.5717(3) 1.0386(3) 0.61404(17) 0.0541(6) Uani 1 1 d . . . . .
C14 C 0.4098(5) 1.1611(4) 0.6190(3) 0.0654(8) Uani 1 1 d . . . . .
H14A H 0.4011 1.2625 0.5908 0.078 Uiso 1 1 calc R U . . .
C15 C 0.2625(4) 1.1083(3) 0.6728(2) 0.0590(7) Uani 1 1 d . . . . .
H15A H 0.1341 1.1684 0.6884 0.071 Uiso 1 1 calc R U . . .
C16 C 0.7704(5) 1.0376(5) 0.5657(2) 0.0748(10) Uani 1 1 d . . . . .
H16A H 0.7703 1.1401 0.5350 0.112 Uiso 1 1 calc R U . . .
H16B H 0.8543 1.0084 0.6145 0.112 Uiso 1 1 calc R U . . .
H16C H 0.8162 0.9637 0.5160 0.112 Uiso 1 1 calc R U . . .


_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 O3 2.006(2) . ?
Co1 O1 2.0080(18) . ?
Co1 N3 2.029(2) . ?
Co1 N1 2.056(2) . ?
O1 C1 1.275(3) . ?
O2 C1 1.236(3) . ?
C1 C2 1.503(3) . ?
C2 C3 1.387(3) . ?
C2 C4 1.388(3) . ?
C3 C4 1.385(3) 2_477 ?
C3 H3A 0.9300 . ?
C4 C3 1.385(3) 2_477 ?
C4 H4A 0.9300 . ?
O3 C5 1.252(4) . ?
O4 C5 1.245(4) . ?
C5 C6 1.504(4) . ?
C6 C7 1.373(4) . ?
C6 C8 1.382(4) . ?
C7 C8 1.388(4) 2_566 ?
C7 H7A 0.9300 . ?
C8 C7 1.388(4) 2_566 ?
C8 H8A 0.9300 . ?
N1 C9 1.306(4) . ?
N1 C11 1.367(4) . ?
C9 N2 1.338(4) . ?
C9 H9A 0.9300 . ?
N2 C10 1.340(4) . ?
N2 C12 1.473(4) . ?
C10 C11 1.344(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N3 C13 1.315(3) . ?
N3 C15 1.367(3) . ?
C13 N4 1.327(3) . ?
C13 H13A 0.9300 . ?
N4 C14 1.350(4) . ?
N4 C16 1.470(4) . ?
C14 C15 1.352(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 Co1 O1 100.01(9) . . ?
O3 Co1 N3 128.41(10) . . ?
O1 Co1 N3 117.77(8) . . ?
O3 Co1 N1 105.26(9) . . ?
O1 Co1 N1 100.00(8) . . ?
N3 Co1 N1 101.44(8) . . ?
C1 O1 Co1 100.28(15) . . ?
O2 C1 O1 122.2(2) . . ?
O2 C1 C2 119.9(2) . . ?
O1 C1 C2 117.8(2) . . ?
C3 C2 C4 119.6(2) . . ?
C3 C2 C1 119.7(2) . . ?
C4 C2 C1 120.7(2) . . ?
C4 C3 C2 120.5(2) 2_477 . ?
C4 C3 H3A 119.7 2_477 . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C2 119.9(2) 2_477 . ?
C3 C4 H4A 120.1 2_477 . ?
C2 C4 H4A 120.1 . . ?
C5 O3 Co1 105.2(2) . . ?
O4 C5 O3 122.0(3) . . ?
O4 C5 C6 120.3(3) . . ?
O3 C5 C6 117.7(3) . . ?
C7 C6 C8 119.6(2) . . ?
C7 C6 C5 120.9(3) . . ?
C8 C6 C5 119.6(3) . . ?
C6 C7 C8 120.4(3) . 2_566 ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 2_566 . ?
C6 C8 C7 120.1(3) . 2_566 ?
C6 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 2_566 . ?
C9 N1 C11 105.3(2) . . ?
C9 N1 Co1 127.38(19) . . ?
C11 N1 Co1 127.1(2) . . ?
N1 C9 N2 111.4(3) . . ?
N1 C9 H9A 124.3 . . ?
N2 C9 H9A 124.3 . . ?
C9 N2 C10 107.1(3) . . ?
C9 N2 C12 124.6(3) . . ?
C10 N2 C12 128.1(3) . . ?
C11 C10 N2 106.9(3) . . ?
C11 C10 H10A 126.6 . . ?
N2 C10 H10A 126.6 . . ?
C10 C11 N1 109.3(3) . . ?
C10 C11 H11A 125.4 . . ?
N1 C11 H11A 125.4 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 N3 C15 104.7(2) . . ?
C13 N3 Co1 123.22(18) . . ?
C15 N3 Co1 131.75(19) . . ?
N3 C13 N4 112.5(2) . . ?
N3 C13 H13A 123.7 . . ?
N4 C13 H13A 123.7 . . ?
C13 N4 C14 106.6(2) . . ?
C13 N4 C16 125.7(3) . . ?
C14 N4 C16 127.7(3) . . ?
C15 C14 N4 107.0(3) . . ?
C15 C14 H14A 126.5 . . ?
N4 C14 H14A 126.5 . . ?
C14 C15 N3 109.2(3) . . ?
C14 C15 H15A 125.4 . . ?
N3 C15 H15A 125.4 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
Co1 O1 C1 O2 -15.5(3) . . . . ?
Co1 O1 C1 C2 161.23(18) . . . . ?
O2 C1 C2 C3 14.1(4) . . . . ?
O1 C1 C2 C3 -162.6(2) . . . . ?
O2 C1 C2 C4 -168.2(2) . . . . ?
O1 C1 C2 C4 15.0(3) . . . . ?
C4 C2 C3 C4 -0.5(4) . . . 2_477 ?
C1 C2 C3 C4 177.2(2) . . . 2_477 ?
C3 C2 C4 C3 0.5(4) . . . 2_477 ?
C1 C2 C4 C3 -177.1(2) . . . 2_477 ?
Co1 O3 C5 O4 5.1(4) . . . . ?
Co1 O3 C5 C6 -173.70(19) . . . . ?
O4 C5 C6 C7 176.2(3) . . . . ?
O3 C5 C6 C7 -5.0(4) . . . . ?
O4 C5 C6 C8 -5.2(4) . . . . ?
O3 C5 C6 C8 173.6(3) . . . . ?
C8 C6 C7 C8 -0.3(5) . . . 2_566 ?
C5 C6 C7 C8 178.4(2) . . . 2_566 ?
C7 C6 C8 C7 0.3(5) . . . 2_566 ?
C5 C6 C8 C7 -178.4(2) . . . 2_566 ?
C11 N1 C9 N2 0.4(3) . . . . ?
Co1 N1 C9 N2 -174.20(19) . . . . ?
N1 C9 N2 C10 -0.4(4) . . . . ?
N1 C9 N2 C12 176.5(3) . . . . ?
C9 N2 C10 C11 0.2(4) . . . . ?
C12 N2 C10 C11 -176.5(3) . . . . ?
N2 C10 C11 N1 0.0(4) . . . . ?
C9 N1 C11 C10 -0.2(4) . . . . ?
Co1 N1 C11 C10 174.4(2) . . . . ?
C15 N3 C13 N4 0.0(3) . . . . ?
Co1 N3 C13 N4 174.00(18) . . . . ?
N3 C13 N4 C14 -0.2(3) . . . . ?
N3 C13 N4 C16 178.6(3) . . . . ?
C13 N4 C14 C15 0.4(3) . . . . ?
C16 N4 C14 C15 -178.4(3) . . . . ?
N4 C14 C15 N3 -0.4(4) . . . . ?
C13 N3 C15 C14 0.3(3) . . . . ?
Co1 N3 C15 C14 -173.0(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
C10 H10A O2 0.93 2.56 3.475(4) 166.7 1_645
C12 H12A O1 0.96 2.84 3.479(4) 125.2 2_667

_refine_diff_density_max         0.462
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.064

