# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_DUT-8Co_op
_database_code_depnum_ccdc_archive 'CCDC 1912199'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2019-04-25 deposited with the CCDC.	2019-09-01 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_DUT-8Co_op          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.905 Why?  
RESPONSE: The dataset was collected on the beamline equipped with 1-axis
goniometer, which allows phi-scans. The orientation of the crystal did 
not allowed to collect 100 % of reflections in this regime.
;
_vrf_PLAT602_DUT-8Co_op          
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info  
RESPONSE: The structure contains large amount of solvent (n-heptane), which
cannot be modelled because of disorder. The SQUEEZE procedure was not applied
in this case because of pseudo-merohedral twinning in the structure
;
_vrf_PLAT770_DUT-8Co_op          
;
PROBLEM: Suspect C-H Bond in CIF:  C7       --H10A      .       1.31 Ang.  
RESPONSE: The bonds are between two separate positions, coming from positional
disorder in the DABCO molecule
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        DUT-8(Co)-heptan
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Co2 N2 O8'
_chemical_formula_weight         658.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3030 1.4690 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   18.720(4)
_cell_length_b                   18.340(4)
_cell_length_c                   9.4900(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.77(3)
_cell_angle_gamma                90
_cell_volume                     3189.6(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    652
_cell_measurement_theta_min      4.53
_cell_measurement_theta_max      22.11

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.685
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.012
_shelx_estimated_absorpt_T_min   0.786
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.89495
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_source_type              'BESSY BL MX-14.3'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_measurement_device_type  'MX-225 CCD'
_diffrn_measurement_method       'Δφ scans'
_diffrn_reflns_number            3012
_diffrn_reflns_av_unetI/netI     0.1308
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.509
_diffrn_reflns_theta_max         33.992
_diffrn_reflns_theta_full        32.478
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 0.905
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.905
_reflns_number_total             3012
_reflns_number_gt                2797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 4-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1419P)²+6.1857P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3012
_refine_ls_number_parameters     118
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0956
_refine_ls_wR_factor_ref         0.2862
_refine_ls_wR_factor_gt          0.2724
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.111
_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_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 0.49302(4) 0.500000 0.35604(10) 0.0307(4) Uani 1 2 d S T P . .
N1 N 0.4985(3) 0.500000 0.1361(8) 0.0410(15) Uani 1 2 d DS T P . .
O1 O 0.4288(2) 0.4224(2) 0.5891(5) 0.0491(10) Uani 1 1 d . . . . .
O2 O 0.4146(2) 0.4229(2) 0.3474(5) 0.0488(10) Uani 1 1 d . . . . .
C1 C 0.3991(3) 0.4012(3) 0.4652(6) 0.0436(12) Uani 1 1 d . . . . .
C2 C 0.3399(3) 0.3449(3) 0.4543(7) 0.0492(14) Uani 1 1 d . . . . .
C3 C 0.3270(3) 0.3118(3) 0.5747(7) 0.0539(15) Uani 1 1 d . . . . .
H3A H 0.355912 0.323810 0.663557 0.065 Uiso 1 1 calc R U . . .
C4 C 0.2709(3) 0.2597(3) 0.5685(7) 0.0540(15) Uani 1 1 d . . . . .
C5 C 0.2565(4) 0.2252(4) 0.6920(8) 0.074(2) Uani 1 1 d . . . . .
H5A H 0.284420 0.237191 0.781731 0.089 Uiso 1 1 calc R U . . .
C6 C 0.2025(4) 0.1746(4) 0.6829(8) 0.072(2) Uani 1 1 d . . . . .
H6A H 0.193279 0.152888 0.765956 0.087 Uiso 1 1 calc R U . . .
C7 C 0.4249(7) 0.500000 0.0456(16) 0.079(5) Uani 0.5 2 d DS TU P . .
H7A H 0.399050 0.542360 0.067440 0.095 Uiso 0.25 1 d R U P . .
H7B H 0.399050 0.457640 0.067440 0.095 Uiso 0.25 1 d R U P . .
C8 C 0.5360(11) 0.4345(9) 0.0980(14) 0.085(5) Uani 0.5 1 d D U P . .
H8A H 0.511165 0.391863 0.121711 0.102 Uiso 0.5 1 d R U P . .
H8B H 0.585195 0.433143 0.152321 0.102 Uiso 0.5 1 d R U P . .
C9 C 0.5731(9) 0.500000 0.114(2) 0.099(7) Uani 0.5 2 d DS TU P . .
H9A H 0.598100 0.457680 0.159258 0.119 Uiso 0.25 1 d R U P . .
H9B H 0.598100 0.542320 0.159258 0.119 Uiso 0.25 1 d R U P . .
C10 C 0.4648(12) 0.4345(9) 0.0637(15) 0.086(4) Uani 0.5 1 d D U P . .
H10A H 0.415367 0.431498 0.076506 0.104 Uiso 0.5 1 d R U P . .
H10B H 0.490447 0.392218 0.107576 0.104 Uiso 0.5 1 d R U P . .


_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 O2 2.027(3) . ?
CO1 O2 2.027(3) 6_565 ?
CO1 O1 2.031(3) 5_666 ?
CO1 O1 2.031(3) 2_656 ?
CO1 N1 2.110(7) . ?
CO1 CO1 2.691(2) 5_666 ?
N1 C9 1.453(15) . ?
N1 C10 1.462(11) 6_565 ?
N1 C10 1.462(11) . ?
N1 C7 1.467(13) . ?
N1 C8 1.472(10) . ?
N1 C8 1.472(10) 6_565 ?
O1 C1 1.256(7) . ?
O1 CO1 2.031(3) 5_666 ?
O2 C1 1.274(7) . ?
C1 C2 1.502(6) . ?
C2 C3 1.359(8) . ?
C2 C6 1.425(8) 7_556 ?
C3 C4 1.413(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.405(10) . ?
C4 C4 1.420(11) 7_556 ?
C5 C6 1.363(8) . ?
C5 H5A 0.9300 . ?
C6 C2 1.425(8) 7_556 ?
C6 H6A 0.9300 . ?
C7 C10 1.41(2) . ?
C7 C10 1.41(2) 6_565 ?
C7 C9 1.527(17) 5_665 ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H10A 1.3106 . ?
C8 C10 1.30(3) . ?
C8 C9 1.38(2) . ?
C8 C10 1.532(14) 2_655 ?
C8 H8A 0.9599 . ?
C8 H8B 0.9601 . ?
C8 H9A 1.2629 . ?
C8 H10B 1.1698 . ?
C9 C8 1.38(2) 6_565 ?
C9 C7 1.527(17) 5_665 ?
C9 H8B 1.2849 . ?
C9 H9A 0.9599 . ?
C9 H9B 0.9599 . ?
C10 C8 1.532(14) 2_655 ?
C10 C10 1.96(4) 2_655 ?
C10 H7B 1.3103 . ?
C10 H8A 1.2125 . ?
C10 H10A 0.9599 . ?
C10 H10B 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
O2 CO1 O2 88.4(3) . 6_565 ?
O2 CO1 O1 167.55(18) . 5_666 ?
O2 CO1 O1 90.0(2) 6_565 5_666 ?
O2 CO1 O1 90.0(2) . 2_656 ?
O2 CO1 O1 167.55(18) 6_565 2_656 ?
O1 CO1 O1 88.9(3) 5_666 2_656 ?
O2 CO1 N1 98.10(18) . . ?
O2 CO1 N1 98.10(18) 6_565 . ?
O1 CO1 N1 94.34(17) 5_666 . ?
O1 CO1 N1 94.34(17) 2_656 . ?
O2 CO1 CO1 87.74(14) . 5_666 ?
O2 CO1 CO1 87.74(13) 6_565 5_666 ?
O1 CO1 CO1 79.86(13) 5_666 5_666 ?
O1 CO1 CO1 79.86(13) 2_656 5_666 ?
N1 CO1 CO1 171.81(16) . 5_666 ?
C9 N1 C10 105.5(10) . 6_565 ?
C9 N1 C10 105.5(10) . . ?
C10 N1 C10 110.6(18) 6_565 . ?
C9 N1 C7 137.0(9) . . ?
C10 N1 C7 57.4(10) 6_565 . ?
C10 N1 C7 57.4(10) . . ?
C9 N1 C8 56.3(10) . . ?
C10 N1 C8 137.4(8) 6_565 . ?
C10 N1 C8 52.8(11) . . ?
C7 N1 C8 107.1(9) . . ?
C9 N1 C8 56.3(10) . 6_565 ?
C10 N1 C8 52.8(11) 6_565 6_565 ?
C10 N1 C8 137.4(8) . 6_565 ?
C7 N1 C8 107.1(9) . 6_565 ?
C8 N1 C8 109.3(18) . 6_565 ?
C9 N1 CO1 112.5(8) . . ?
C10 N1 CO1 111.2(6) 6_565 . ?
C10 N1 CO1 111.2(6) . . ?
C7 N1 CO1 110.5(7) . . ?
C8 N1 CO1 111.4(6) . . ?
C8 N1 CO1 111.4(6) 6_565 . ?
C1 O1 CO1 128.0(4) . 5_666 ?
C1 O2 CO1 118.4(4) . . ?
O1 C1 O2 126.0(5) . . ?
O1 C1 C2 117.2(5) . . ?
O2 C1 C2 116.8(5) . . ?
C3 C2 C6 119.7(5) . 7_556 ?
C3 C2 C1 120.3(5) . . ?
C6 C2 C1 120.1(5) 7_556 . ?
C2 C3 C4 121.7(5) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C5 C4 C3 122.5(6) . . ?
C5 C4 C4 119.1(6) . 7_556 ?
C3 C4 C4 118.3(7) . 7_556 ?
C6 C5 C4 121.3(6) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C2 119.8(6) . 7_556 ?
C5 C6 H6A 120.1 . . ?
C2 C6 H6A 120.1 7_556 . ?
C10 C7 C10 117.3(16) . 6_565 ?
C10 C7 N1 61.1(8) . . ?
C10 C7 N1 61.1(8) 6_565 . ?
C10 C7 C9 90.1(10) . 5_665 ?
C10 C7 C9 90.1(10) 6_565 5_665 ?
N1 C7 C9 111.8(12) . 5_665 ?
C10 C7 H7A 160.6 . . ?
C10 C7 H7A 64.0 6_565 . ?
N1 C7 H7A 109.2 . . ?
C9 C7 H7A 109.3 5_665 . ?
C10 C7 H7B 64.0 . . ?
C10 C7 H7B 160.6 6_565 . ?
N1 C7 H7B 109.2 . . ?
C9 C7 H7B 109.3 5_665 . ?
H7A C7 H7B 108.0 . . ?
C10 C7 H10A 41.2 . . ?
C10 C7 H10A 152.2 6_565 . ?
N1 C7 H10A 91.4 . . ?
C9 C7 H10A 104.7 5_665 . ?
H7A C7 H10A 129.0 . . ?
H7B C7 H10A 22.8 . . ?
C10 C8 C9 119.6(12) . . ?
C10 C8 N1 63.2(8) . . ?
C9 C8 N1 61.1(8) . . ?
C10 C8 C10 87.1(16) . 2_655 ?
C9 C8 C10 90.9(17) . 2_655 ?
N1 C8 C10 109.8(10) . 2_655 ?
C10 C8 H8A 62.6 . . ?
C9 C8 H8A 160.0 . . ?
N1 C8 H8A 109.3 . . ?
C10 C8 H8A 109.1 2_655 . ?
C10 C8 H8B 162.4 . . ?
C9 C8 H8B 63.7 . . ?
N1 C8 H8B 110.1 . . ?
C10 C8 H8B 110.5 2_655 . ?
H8A C8 H8B 108.0 . . ?
C10 C8 H9A 155.9 . . ?
C9 C8 H9A 42.3 . . ?
N1 C8 H9A 93.1 . . ?
C10 C8 H9A 106.3 2_655 . ?
H8A C8 H9A 127.6 . . ?
H8B C8 H9A 21.4 . . ?
C10 C8 H10B 45.3 . . ?
C9 C8 H10B 157.9 . . ?
N1 C8 H10B 97.5 . . ?
C10 C8 H10B 102.6 2_655 . ?
H8A C8 H10B 17.4 . . ?
H8B C8 H10B 125.1 . . ?
H9A C8 H10B 143.5 . . ?
C8 C9 C8 120.9(17) . 6_565 ?
C8 C9 N1 62.6(8) . . ?
C8 C9 N1 62.6(8) 6_565 . ?
C8 C9 C7 90.1(10) . 5_665 ?
C8 C9 C7 90.1(10) 6_565 5_665 ?
N1 C9 C7 111.1(13) . 5_665 ?
C8 C9 H8B 42.0 . . ?
C8 C9 H8B 156.6 6_565 . ?
N1 C9 H8B 94.6 . . ?
C7 C9 H8B 103.9 5_665 . ?
C8 C9 H9A 62.3 . . ?
C8 C9 H9A 160.4 6_565 . ?
N1 C9 H9A 109.4 . . ?
C7 C9 H9A 109.4 5_665 . ?
H8B C9 H9A 20.3 . . ?
C8 C9 H9B 160.4 . . ?
C8 C9 H9B 62.3 6_565 . ?
N1 C9 H9B 109.4 . . ?
C7 C9 H9B 109.4 5_665 . ?
H8B C9 H9B 127.2 . . ?
H9A C9 H9B 107.9 . . ?
C8 C10 C7 121.3(12) . . ?
C8 C10 N1 64.0(8) . . ?
C7 C10 N1 61.5(8) . . ?
C8 C10 C8 92.9(16) . 2_655 ?
C7 C10 C8 88.9(16) . 2_655 ?
N1 C10 C8 112.7(11) . 2_655 ?
C8 C10 C10 51.3(11) . 2_655 ?
C7 C10 C10 109.4(10) . 2_655 ?
N1 C10 C10 90.6(12) . 2_655 ?
C8 C10 C10 41.6(9) 2_655 2_655 ?
C8 C10 H7B 155.5 . . ?
C7 C10 H7B 41.2 . . ?
N1 C10 H7B 92.2 . . ?
C8 C10 H7B 102.1 2_655 . ?
C10 C10 H7B 140.3 2_655 . ?
C8 C10 H8A 44.7 . . ?
C7 C10 H8A 156.7 . . ?
N1 C10 H8A 96.7 . . ?
C8 C10 H8A 108.4 2_655 . ?
C10 C10 H8A 76.8 2_655 . ?
H7B C10 H8A 141.8 . . ?
C8 C10 H10A 158.5 . . ?
C7 C10 H10A 64.0 . . ?
N1 C10 H10A 108.8 . . ?
C8 C10 H10A 108.3 2_655 . ?
C10 C10 H10A 149.8 2_655 . ?
H7B C10 H10A 22.8 . . ?
H8A C10 H10A 121.7 . . ?
C8 C10 H10B 59.9 . . ?
C7 C10 H10B 161.4 . . ?
N1 C10 H10B 109.3 . . ?
C8 C10 H10B 109.7 2_655 . ?
C10 C10 H10B 85.9 2_655 . ?
H7B C10 H10B 129.7 . . ?
H8A C10 H10B 15.4 . . ?
H10A C10 H10B 108.0 . . ?

_refine_diff_density_max         1.015
_refine_diff_density_min         -1.314
_refine_diff_density_rms         0.150


_exptl_crystal_recrystallization_method 'solvent exchange'
_chemical_properties_physical    Moisture-sensitive
