# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Co-pydc
_database_code_depnum_ccdc_archive 'CCDC 1851529'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_audit_creation_date             2018-06-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        Co-pydc
_chemical_formula_moiety         '0.5(C58 H36 Co6 N2 O32)'
_chemical_formula_sum            'C29 H18 Co3 N O16'
_chemical_formula_weight         813.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Co'
_chemical_oxdiff_usercomment     st
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'
Co Co 0.3494 0.9721 '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'

_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.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           190
_space_group_name_H-M_alt        'P -6 2 c'
_space_group_name_Hall           'P -6c -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z+1/2'
'-y, x-y, -z+1/2'
'-x+y, -x, -z+1/2'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, z+1/2'

_cell_length_a                   14.5594(5)
_cell_length_b                   14.5594(5)
_cell_length_c                   13.7247(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2519.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5314
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.5970
_cell_measurement_theta_min      2.2240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12677
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.494
_diffrn_reflns_theta_min         2.193
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  41.00   0.50    1.00    --    6.80 -57.00  30.00  210
  2  ω    -78.00  -9.00   0.50    1.00    --   -7.10 -57.00-120.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0435698000
_diffrn_orient_matrix_UB_12      0.0090306000
_diffrn_orient_matrix_UB_13      -0.0011338000
_diffrn_orient_matrix_UB_21      0.0350457000
_diffrn_orient_matrix_UB_22      0.0549758000
_diffrn_orient_matrix_UB_23      0.0075872000
_diffrn_orient_matrix_UB_31      0.0061842000
_diffrn_orient_matrix_UB_32      0.0079647000
_diffrn_orient_matrix_UB_33      -0.0511235000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                1706
_reflns_number_total             1821
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.004(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1821
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0317P)²+0.7485P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0691
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups, All O(H,H) groups
2. Shared sites
{C7, N1}
3. Restrained distances
 O2-H2B
 0.85 with sigma of 0.01
 O2-H2A
 0.85 with sigma of 0.01
 H2A-H2B
 1.23 with sigma of 0.01
4. Rigid bond restraints
 Co1, O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(Co1) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C7) = Uanis(N1)
6. Others
 Fixed Sof: C7(0.33333) N1(0.16667) H1(0.33333) H1A(0.16667)
7.a Ternary CH refined with riding coordinates:
 O1(H1A)
7.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), N1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.18783(4) 0.53524(4) 0.7500 0.01719(16) Uani 1 2 d S TU P . .
O4 O 0.40620(18) 0.53544(17) 0.64289(18) 0.0366(6) Uani 1 1 d . . . . .
O3 O 0.2310(2) 0.4623(2) 0.6452(2) 0.0466(7) Uani 1 1 d . . . . .
C7 C 0.0956(2) 0.0000 0.5000 0.0191(8) Uani 0.6667 2 d S T P A 3
O2 O 0.0388(3) 0.3946(3) 0.7500 0.0601(14) Uani 1 2 d DS T P . .
H2A H 0.003(4) 0.3282(11) 0.7500 0.072 Uiso 1 2 d DRS T P . .
H2B H -0.015(3) 0.402(5) 0.7500 0.072 Uiso 1 2 d DRS T P . .
C6 C 0.0947(3) 0.0947(3) 0.5000 0.0190(9) Uani 1 2 d S T P . .
C4 C 0.2069(2) 0.2831(2) 0.5536(2) 0.0241(7) Uani 1 1 d . . . . .
H4 H 0.1491 0.2779 0.5873 0.029 Uiso 1 1 calc R . . A .
C2 C 0.3034(2) 0.3767(2) 0.5563(2) 0.0257(7) Uani 1 1 d . . . . .
C5 C 0.1962(3) 0.1962(3) 0.5000 0.0236(10) Uani 1 2 d S T P A .
C1 C 0.3151(3) 0.4662(2) 0.6195(2) 0.0273(7) Uani 1 1 d . . . . .
C3 C 0.3871(3) 0.3871(3) 0.5000 0.0280(11) Uani 1 2 d S T P . .
H3 H 0.4510 0.4510 0.5000 0.034 Uiso 1 2 calc RS T P . .
N1 N 0.0956(2) 0.0000 0.5000 0.0191(8) Uani 0.3333 2 d S T P A 4
H1 H 0.1547 0.0000 0.5000 0.023 Uiso 0.6667 2 calc RS T P A 4
O1 O 0.3333 0.6667 0.7500 0.0108(8) Uani 1 6 d S TU P . .
H1A H 0.3333 0.6667 0.8214 0.013 Uiso 0.5 3 calc RS T 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 O4 2.084(2) 3_565 ?
Co1 O4 2.084(2) 6_566 ?
Co1 O3 2.063(2) . ?
Co1 O3 2.063(2) 4_556 ?
Co1 O2 2.112(4) . ?
Co1 O1 2.0238(5) . ?
O4 Co1 2.084(2) 2_665 ?
O4 C1 1.242(4) . ?
O3 C1 1.248(4) . ?
C7 C6 1.386(3) . ?
C7 C6 1.386(3) 3 ?
O2 H2A 0.838(14) . ?
O2 H2B 0.851(14) . ?
C6 C7 1.386(3) 2 ?
C6 C5 1.477(6) . ?
C6 N1 1.386(3) 2 ?
C4 H4 0.9300 . ?
C4 C2 1.384(4) . ?
C4 C5 1.404(4) . ?
C2 C1 1.503(4) . ?
C2 C3 1.386(4) . ?
C5 C4 1.404(4) 7_556 ?
C3 C2 1.386(4) 7_556 ?
C3 H3 0.9300 . ?
O1 Co1 2.0238(5) 2_665 ?
O1 Co1 2.0238(5) 3_565 ?
O1 H1A 0.9800 . ?

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 O4 89.73(14) 6_566 3_565 ?
O4 Co1 O2 87.97(11) 3_565 . ?
O4 Co1 O2 87.97(11) 6_566 . ?
O3 Co1 O4 173.96(11) . 6_566 ?
O3 Co1 O4 90.63(11) . 3_565 ?
O3 Co1 O4 90.63(11) 4_556 6_566 ?
O3 Co1 O4 173.96(11) 4_556 3_565 ?
O3 Co1 O3 88.39(16) 4_556 . ?
O3 Co1 O2 86.02(11) 4_556 . ?
O3 Co1 O2 86.02(11) . . ?
O1 Co1 O4 93.57(7) . 3_565 ?
O1 Co1 O4 93.57(7) . 6_566 ?
O1 Co1 O3 92.42(7) . 4_556 ?
O1 Co1 O3 92.42(7) . . ?
O1 Co1 O2 177.82(12) . . ?
C1 O4 Co1 132.9(2) . 2_665 ?
C1 O3 Co1 135.9(2) . . ?
C6 C7 C6 119.1(4) 3 . ?
Co1 O2 H2A 150(4) . . ?
Co1 O2 H2B 116(4) . . ?
H2A O2 H2B 94.1(19) . . ?
C7 C6 C7 120.9(4) . 2 ?
C7 C6 C5 119.53(19) . . ?
C7 C6 C5 119.53(19) 2 . ?
N1 C6 C5 119.53(19) 2 . ?
C2 C4 H4 119.9 . . ?
C2 C4 C5 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C2 C1 119.2(3) . . ?
C4 C2 C3 119.8(3) . . ?
C3 C2 C1 121.0(3) . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 C6 120.5(2) 7_556 . ?
C4 C5 C4 119.1(4) . 7_556 ?
O4 C1 O3 126.1(3) . . ?
O4 C1 C2 117.7(3) . . ?
O3 C1 C2 116.2(3) . . ?
C2 C3 C2 120.7(4) 7_556 . ?
C2 C3 H3 119.6 7_556 . ?
C2 C3 H3 119.6 . . ?
Co1 O1 Co1 119.999(1) . 2_665 ?
Co1 O1 Co1 120.0 3_565 . ?
Co1 O1 Co1 120.0 3_565 2_665 ?
Co1 O1 H1A 90.0 3_565 . ?
Co1 O1 H1A 90.0 . . ?
Co1 O1 H1A 90.0 2_665 . ?

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 O4 C1 O3 14.5(6) 2_665 . . . ?
Co1 O4 C1 C2 -163.9(2) 2_665 . . . ?
Co1 O3 C1 O4 -14.4(6) . . . . ?
Co1 O3 C1 C2 164.0(3) . . . . ?
C7 C6 C5 C4 -142.58(15) . . . . ?
C7 C6 C5 C4 37.42(15) . . . 7_556 ?
C7 C6 C5 C4 37.42(15) 2 . . . ?
C7 C6 C5 C4 -142.58(15) 2 . . 7_556 ?
C6 C7 C6 C7 0.0 3 . . 2 ?
C6 C7 C6 C5 180.0 3 . . . ?
C6 C7 C6 N1 0.0 3 . . 2 ?
C4 C2 C1 O4 159.8(3) . . . . ?
C4 C2 C1 O3 -18.7(5) . . . . ?
C4 C2 C3 C2 -2.5(2) . . . 7_556 ?
C2 C4 C5 C6 177.5(2) . . . . ?
C2 C4 C5 C4 -2.5(2) . . . 7_556 ?
C5 C4 C2 C1 -175.9(3) . . . . ?
C5 C4 C2 C3 5.0(4) . . . . ?
C1 C2 C3 C2 178.4(3) . . . 7_556 ?
C3 C2 C1 O4 -21.1(5) . . . . ?
C3 C2 C1 O3 160.4(3) . . . . ?
N1 C6 C5 C4 -142.58(15) 2 . . 7_556 ?
N1 C6 C5 C4 37.42(15) 2 . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.113 -0.166 -0.611 1350.6 808.4 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.589
####################################################################### 
# 
# 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_Co-pydc-TPB-activated
_database_code_depnum_ccdc_archive 'CCDC 1851531'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        Co-pydc-TPB-activated
_chemical_formula_moiety         '0.5(C100.02 H56 Co6 N8 O26)'
_chemical_formula_sum            'C50.01 H28 Co3 N4 O13'
_chemical_formula_weight         1069.67
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S Fe F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           190
_space_group_name_H-M_alt        'P -6 2 c'
_space_group_name_Hall           'P -6c -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x, y, -z+1/2'
'-y, x-y, -z+1/2'
'-x+y, -x, -z+1/2'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, z+1/2'

_cell_length_a                   14.3406(2)
_cell_length_b                   14.3406(2)
_cell_length_c                   14.1626(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2522.37(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4500
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3780
_cell_measurement_theta_min      3.5380
_shelx_estimated_absorpt_T_max   0.495
_shelx_estimated_absorpt_T_min   0.495
_exptl_absorpt_coefficient_mu    8.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1082
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9154
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.490
_diffrn_reflns_theta_min         3.559
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  51.00   0.50    0.50    --    0.00  77.00-150.00  126
  2  ω    -15.00  12.00   0.50    0.50    --    0.00  38.00  30.00   54
  3  ω     56.00  84.00   0.50    0.50    --    0.00  77.00-150.00   56
  4  ω     24.00 119.00   0.50    4.00    --   95.20 -61.00-120.00  190
  5  ω     12.00 107.00   0.50    4.00    --   95.20 -45.00 -30.00  190
  6  ω      9.00  98.00   0.50    4.00    --   95.20 -61.00 -30.00  178
  7  ω     40.00 117.00   0.50    4.00    --   95.20 -82.00-120.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0070226000
_diffrn_orient_matrix_UB_12      -0.0212469000
_diffrn_orient_matrix_UB_13      0.1071371000
_diffrn_orient_matrix_UB_21      -0.0581741000
_diffrn_orient_matrix_UB_22      -0.1220951000
_diffrn_orient_matrix_UB_23      -0.0187498000
_diffrn_orient_matrix_UB_31      0.1093347000
_diffrn_orient_matrix_UB_32      0.0039912000
_diffrn_orient_matrix_UB_33      -0.0031314000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                1414
_reflns_number_total             1526
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 
;
 Flack x determined using 562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.008(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1526
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1033P)²+3.9798P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1659
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2. Shared sites
{C14, N2}
3. Restrained distances
 C6-C2
 1.38 with sigma of 0.02
 N1-C2
 1.32 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C14) = Uanis(N2)
5. Others
 Fixed Sof: H1(0.16667) C14(0.335) C2(0.5) H2(0.5) C6(0.5) C4(0.5) H4(0.5)
 C3(0.5) H3(0.5) C5(0.5) H5(0.5) N2(0.16667)
6.a Ternary CH refined with riding coordinates:
 O1(H1)
6.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C8(H8), C2(H2), C4(H4), C3(H3), C11(H11), C9(H9), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.18617(11) 0.52998(11) 0.7500 0.0264(5) Uani 1 2 d S T P B .
O1 O 0.3333 0.6667 0.7500 0.028(3) Uani 1 6 d S T P . .
H1 H 0.3333 0.6667 0.8206 0.033 Uiso 0.5 3 calc RS T P . .
C14 C 0.0969(6) 0.0000 0.5000 0.0280(19) Uani 0.67 2 d S T P A 3
H14 H 0.1631 0.0000 0.5000 0.034 Uiso 1 2 calc RS T P . .
C13 C 0.0970(6) 0.0970(6) 0.5000 0.027(2) Uani 1 2 d S T P . .
O3 O 0.4154(5) 0.5387(5) 0.6448(5) 0.063(2) Uani 1 1 d . . . . .
O2 O 0.2382(5) 0.4658(5) 0.6471(6) 0.069(2) Uani 1 1 d . . . . .
C8 C -0.1021(8) -0.0149(9) 0.7500 0.038(2) Uani 1 2 d S T P . .
H8 H -0.1731 -0.0258 0.7500 0.046 Uiso 1 2 calc RS T P . .
N1 N 0.0389(8) 0.3763(8) 0.7500 0.051(3) Uani 1 2 d DS T P . .
C2 C 0.0480(9) 0.2871(9) 0.746(6) 0.035(5) Uani 0.5 1 d D . . B -1
H2 H 0.1182 0.2970 0.7543 0.041 Uiso 0.5 1 calc R . . B -1
C6 C -0.0344(12) 0.1829(10) 0.7317(15) 0.037(7) Uani 0.5 1 d D . . B -1
C4 C -0.1451(19) 0.2584(19) 0.696(2) 0.083(7) Uani 0.5 1 d . U . B -1
H4 H -0.2121 0.2495 0.6752 0.100 Uiso 0.5 1 calc R . . B -1
C3 C -0.0569(17) 0.3613(16) 0.7142(15) 0.064(6) Uani 0.5 1 d . U . B -1
H3 H -0.0637 0.4226 0.7015 0.077 Uiso 0.5 1 calc R . . B -1
C7 C -0.0168(9) 0.0876(8) 0.7500 0.036(2) Uani 1 2 d S T P . .
C11 C 0.2115(6) 0.2863(6) 0.5524(6) 0.0380(17) Uani 1 1 d . . . . .
H11 H 0.1519 0.2806 0.5866 0.046 Uiso 1 1 calc R . . A .
C12 C 0.1995(7) 0.1995(7) 0.5000 0.035(2) Uani 1 2 d S T P A .
C9 C 0.3956(8) 0.3956(8) 0.5000 0.052(3) Uani 1 2 d S T P . .
H9 H 0.4618 0.4618 0.5000 0.063 Uiso 1 2 calc RS T P . .
C10 C 0.3096(6) 0.3815(7) 0.5556(6) 0.0439(19) Uani 1 1 d . . . . .
C1 C 0.3224(6) 0.4687(6) 0.6225(6) 0.0418(19) Uani 1 1 d . . . . .
C5 C -0.1311(18) 0.1720(18) 0.7087(16) 0.067(6) Uani 0.5 1 d . U . B -1
H5 H -0.1912 0.1016 0.7011 0.080 Uiso 0.5 1 calc R . . B -1
N2 N 0.0969(6) 0.0000 0.5000 0.0280(19) Uani 0.3333 2 d S T P A 4


_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 O1 2.0395(14) . ?
Co1 O3 2.086(6) 6_566 ?
Co1 O3 2.086(6) 3_565 ?
Co1 O2 2.052(6) 4_556 ?
Co1 O2 2.052(6) . ?
Co1 N1 2.159(11) . ?
O1 Co1 2.0394(14) 3_565 ?
O1 Co1 2.0394(14) 2_665 ?
O1 H1 1.0000 . ?
C14 H14 0.9500 . ?
C14 C13 1.390(6) . ?
C14 C13 1.390(6) 3 ?
C13 C14 1.390(6) 2 ?
C13 C12 1.470(13) . ?
C13 N2 1.390(6) 2 ?
O3 Co1 2.086(6) 2_665 ?
O3 C1 1.244(10) . ?
O2 C1 1.237(10) . ?
C8 H8 0.9500 . ?
C8 C7 1.399(15) 2 ?
C8 C7 1.363(15) . ?
N1 C2 1.350(13) . ?
N1 C3 1.38(2) . ?
C2 H2 0.9500 . ?
C2 C6 1.380(19) . ?
C6 C7 1.531(16) . ?
C6 C5 1.35(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.41(3) . ?
C4 C5 1.36(3) . ?
C3 H3 0.9500 . ?
C7 C8 1.399(15) 3 ?
C11 H11 0.9500 . ?
C11 C12 1.384(9) . ?
C11 C10 1.387(11) . ?
C12 C11 1.384(9) 7_556 ?
C9 H9 0.9500 . ?
C9 C10 1.389(9) . ?
C9 C10 1.389(9) 7_556 ?
C10 C1 1.506(11) . ?
C5 H5 0.9500 . ?

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
O1 Co1 O3 94.17(19) . 3_565 ?
O1 Co1 O3 94.17(19) . 6_566 ?
O1 Co1 O2 89.84(17) . 4_556 ?
O1 Co1 O2 89.85(17) . . ?
O1 Co1 N1 174.2(2) . . ?
O3 Co1 O3 91.2(5) 3_565 6_566 ?
O3 Co1 N1 89.9(2) 3_565 . ?
O3 Co1 N1 89.9(2) 6_566 . ?
O2 Co1 O3 89.0(4) . 3_565 ?
O2 Co1 O3 176.0(3) 4_556 3_565 ?
O2 Co1 O3 89.0(4) 4_556 6_566 ?
O2 Co1 O3 176.0(3) . 6_566 ?
O2 Co1 O2 90.5(5) 4_556 . ?
O2 Co1 N1 86.1(2) . . ?
O2 Co1 N1 86.1(2) 4_556 . ?
Co1 O1 Co1 120.0 3_565 . ?
Co1 O1 Co1 120.0 . 2_665 ?
Co1 O1 Co1 120.000(1) 3_565 2_665 ?
Co1 O1 H1 90.0 3_565 . ?
Co1 O1 H1 90.0 2_665 . ?
Co1 O1 H1 90.0 . . ?
C13 C14 H14 119.9 3 . ?
C13 C14 H14 119.9 . . ?
C13 C14 C13 120.1(8) . 3 ?
C14 C13 C14 119.9(8) 2 . ?
C14 C13 C12 120.1(4) 2 . ?
C14 C13 C12 120.1(4) . . ?
N2 C13 C12 120.1(4) 2 . ?
C1 O3 Co1 130.6(6) . 2_665 ?
C1 O2 Co1 138.8(6) . . ?
C7 C8 H8 119.2 2 . ?
C7 C8 H8 119.2 . . ?
C7 C8 C7 121.7(10) . 2 ?
C2 N1 Co1 117.3(8) . . ?
C2 N1 C3 113.5(19) . . ?
C3 N1 Co1 123.4(10) . . ?
N1 C2 H2 116.7 . . ?
N1 C2 C6 126.5(15) . . ?
C6 C2 H2 116.7 . . ?
C2 C6 C7 120.4(15) . . ?
C5 C6 C2 115.8(17) . . ?
C5 C6 C7 123.6(15) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C5 C4 C3 118(2) . . ?
N1 C3 C4 122.4(17) . . ?
N1 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C8 C7 C8 118.3(10) . 3 ?
C8 C7 C6 120.5(10) 3 . ?
C8 C7 C6 120.2(11) . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C10 120.7(7) . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.8(5) 7_556 . ?
C11 C12 C13 120.8(5) . . ?
C11 C12 C11 118.5(10) 7_556 . ?
C10 C9 H9 121.1 7_556 . ?
C10 C9 H9 121.1 . . ?
C10 C9 C10 117.8(10) 7_556 . ?
C11 C10 C9 121.0(7) . . ?
C11 C10 C1 118.6(7) . . ?
C9 C10 C1 120.3(8) . . ?
O3 C1 C10 117.8(7) . . ?
O2 C1 O3 126.1(8) . . ?
O2 C1 C10 116.0(7) . . ?
C6 C5 C4 122(2) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?

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 O3 C1 O2 14.8(17) 2_665 . . . ?
Co1 O3 C1 C10 -168.2(6) 2_665 . . . ?
Co1 O2 C1 O3 -19.1(19) . . . . ?
Co1 O2 C1 C10 163.9(7) . . . . ?
Co1 N1 C2 C6 -170(5) . . . . ?
Co1 N1 C3 C4 165.8(18) . . . . ?
C14 C13 C12 C11 38.6(4) . . . 7_556 ?
C14 C13 C12 C11 38.6(4) 2 . . . ?
C14 C13 C12 C11 -141.4(4) . . . . ?
C14 C13 C12 C11 -141.4(4) 2 . . 7_556 ?
C13 C14 C13 C14 0.000(0) 3 . . 2 ?
C13 C14 C13 C12 180.000(0) 3 . . . ?
C13 C14 C13 N2 0.000(0) 3 . . 2 ?
N1 C2 C6 C7 -167(5) . . . . ?
N1 C2 C6 C5 8(8) . . . . ?
C2 N1 C3 C4 13(4) . . . . ?
C2 C6 C7 C8 -22(4) . . . 3 ?
C2 C6 C7 C8 170(4) . . . . ?
C2 C6 C5 C4 3(5) . . . . ?
C3 N1 C2 C6 -16(8) . . . . ?
C3 C4 C5 C6 -5(4) . . . . ?
C7 C8 C7 C8 0.000(1) 2 . . 3 ?
C7 C8 C7 C6 168.7(9) 2 . . . ?
C7 C6 C5 C4 178(2) . . . . ?
C11 C10 C1 O3 160.0(9) . . . . ?
C11 C10 C1 O2 -22.8(13) . . . . ?
C12 C11 C10 C9 5.6(13) . . . . ?
C12 C11 C10 C1 -172.8(7) . . . . ?
C9 C10 C1 O3 -18.5(13) . . . . ?
C9 C10 C1 O2 158.8(8) . . . . ?
C10 C11 C12 C13 177.2(6) . . . . ?
C10 C11 C12 C11 -2.8(6) . . . 7_556 ?
C10 C9 C10 C11 -2.8(6) 7_556 . . . ?
C10 C9 C10 C1 175.6(9) 7_556 . . . ?
C5 C6 C7 C8 -5(2) . . . . ?
C5 C6 C7 C8 163.8(16) . . . 3 ?
C5 C4 C3 N1 -4(4) . . . . ?
N2 C13 C12 C11 38.6(4) 2 . . . ?
N2 C13 C12 C11 -141.4(4) 2 . . 7_556 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.642
####################################################################### 
# 
# 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_Co-pydc-TPB
_database_code_depnum_ccdc_archive 'CCDC 1851530'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        Co-pydc-TPB
_chemical_formula_moiety         '0.5(C100.02 H56 Co6 N8 O26)'
_chemical_formula_sum            'C50.01 H28 Co3 N4 O13'
_chemical_formula_weight         1069.67
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Co'
_chemical_oxdiff_usercomment     st
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           190
_space_group_name_H-M_alt        'P -6 2 c'
_space_group_name_Hall           'P -6c -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+y, -x, -z+1/2'
'-y, x-y, z'
'x, y, -z+1/2'
'-x+y, -x, z'
'-y, x-y, -z+1/2'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, -z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, z+1/2'

_cell_length_a                   14.3390(2)
_cell_length_b                   14.3390(2)
_cell_length_c                   14.3590(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2556.78(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3907
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.3450
_cell_measurement_theta_min      3.5500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1082
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8196
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.395
_diffrn_reflns_theta_min         3.559
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  75.00   0.50    0.50    --   45.70 -19.00 120.00  178
  2  ω    100.00 129.00   0.50    0.50    --   45.70 -19.00 120.00   58
  3  ω    113.00 139.00   0.50    1.50    --  100.10 -79.00 159.00   52
  4  ω     21.00  81.00   0.50    1.50    --  100.10 -79.00 159.00  120
  5  ω     94.00 181.00   0.50    1.50    --  100.10  82.00 -60.00  174
  6  ω     88.00 179.00   0.50    1.50    --  100.10  82.00 -90.00  182
  7  ω     86.00 188.00   0.50    1.50    --  100.10  77.00   0.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1183085000
_diffrn_orient_matrix_UB_12      -0.0785838000
_diffrn_orient_matrix_UB_13      -0.0258168000
_diffrn_orient_matrix_UB_21      0.0350603000
_diffrn_orient_matrix_UB_22      -0.0699560000
_diffrn_orient_matrix_UB_23      -0.0544425000
_diffrn_orient_matrix_UB_31      -0.0128652000
_diffrn_orient_matrix_UB_32      -0.0656950000
_diffrn_orient_matrix_UB_33      0.0887657000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                1510
_reflns_number_total             1654
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 
;
 Flack x determined using 555 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.013(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1654
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1370P)²+2.2804P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1835
_refine_ls_wR_factor_ref         0.1914
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2. Shared sites
{C14, N2}
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14) = Uanis(N2)
4. Others
 Fixed Sof: H1(0.16667) C14(0.335) C3(0.5) H3(0.5) N1(0.5) C2(0.5) H2(0.5)
 C5(0.5) C6(0.5) H6(0.5) C4(0.5) H4(0.5) N2(0.16667)
5.a Ternary CH refined with riding coordinates:
 O1(H1)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C11(H11), C10(H10), C3(H3), C2(H2), C6(H6), C4(H4)
5.c Fitted hexagon refined as free rotating group:
 C3(N1,C2,C5,C6,C4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.34398(11) 0.53012(11) 0.7500 0.0183(4) Uani 1 2 d S T P . .
O1 O 0.3333 0.6667 0.7500 0.0083(18) Uani 1 6 d S T P B .
H1 H 0.3333 0.6667 0.6818 0.010 Uiso 0.5 3 calc RS T P . .
O2 O 0.4620(4) 0.5829(4) 0.6469(4) 0.0383(14) Uani 1 1 d . . . . .
O3 O 0.5365(4) 0.7636(5) 0.6482(4) 0.0396(14) Uani 1 1 d . . . . .
C7 C 0.1061(8) 0.0892(8) 0.7500 0.033(2) Uani 1 2 d S T P . .
C1 C 0.5295(6) 0.6764(6) 0.6230(5) 0.0306(17) Uani 1 1 d . . . . .
C8 C 0.0878(8) -0.0154(8) 0.7500 0.028(2) Uani 1 2 d S T P B .
H8 H 0.1466 -0.0261 0.7500 0.034 Uiso 1 2 calc RS T P . .
C14 C 0.9029(6) 1.0000 0.5000 0.0249(19) Uani 0.67 2 d S T P A 3
H14 H 0.8381 1.0000 0.5000 0.030 Uiso 1 2 calc RS T P . .
C11 C 0.7127(6) 0.7862(7) 0.5529(5) 0.0334(17) Uani 1 1 d . . . . .
H11 H 0.7191 0.8443 0.5869 0.040 Uiso 1 1 calc R . . . .
C9 C 0.6175(6) 0.6893(6) 0.5561(5) 0.0327(17) Uani 1 1 d . . . . .
C12 C 0.7990(7) 0.7990(7) 0.5000 0.027(2) Uani 1 2 d S T P A .
C13 C 0.9051(6) 0.9051(6) 0.5000 0.0207(19) Uani 1 2 d S T P . .
C10 C 0.6045(8) 0.6045(8) 0.5000 0.048(3) Uani 1 2 d S T P . .
H10 H 0.5396 0.5396 0.5000 0.057 Uiso 1 2 calc RS T P . .
C3 C 0.4186(7) 0.3649(7) 0.7012(15) 0.058(6) Uani 0.5 1 d . . . B -2
H3 H 0.4855 0.4254 0.6903 0.069 Uiso 0.5 1 calc R . . B -2
N1 N 0.3360(7) 0.3761(5) 0.7401(18) 0.040(4) Uani 0.5 1 d G . . B -2
C2 C 0.2361(6) 0.2856(7) 0.756(2) 0.026(3) Uani 0.5 1 d G . . B -2
H2 H 0.1808 0.2931 0.7825 0.031 Uiso 0.5 1 calc R . . B -2
C5 C 0.2189(7) 0.1839(5) 0.7340(18) 0.058(9) Uani 0.5 1 d G . . B -2
C6 C 0.3015(10) 0.1727(7) 0.6951(14) 0.067(7) Uani 0.5 1 d G . . B -2
H6 H 0.2899 0.1046 0.6801 0.080 Uiso 0.5 1 calc R . . B -2
C4 C 0.4014(10) 0.2632(9) 0.6787(12) 0.071(6) Uani 0.5 1 d G U . B -2
H4 H 0.4567 0.2556 0.6527 0.086 Uiso 0.5 1 calc R . . B -2
N2 N 0.9029(6) 1.0000 0.5000 0.0249(19) Uani 0.3333 2 d S T P A 4


_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 O1 2.0385(13) . ?
Co1 O2 2.085(5) 4_556 ?
Co1 O2 2.085(5) . ?
Co1 O3 2.063(5) 5_565 ?
Co1 O3 2.063(5) 2_566 ?
Co1 N1 2.158(6) . ?
O1 Co1 2.0385(13) 2_566 ?
O1 Co1 2.0385(14) 3_665 ?
O1 H1 0.9800 . ?
O2 C1 1.246(9) . ?
O3 Co1 2.063(5) 3_665 ?
O3 C1 1.257(10) . ?
C7 C8 1.387(14) . ?
C7 C8 1.412(14) 3 ?
C7 C5 1.521(12) . ?
C1 C9 1.522(10) . ?
C8 C7 1.412(14) 2_556 ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.376(6) . ?
C14 C13 1.376(6) 5_675 ?
C11 H11 0.9300 . ?
C11 C9 1.378(12) . ?
C11 C12 1.383(9) . ?
C9 C10 1.392(9) . ?
C12 C11 1.383(9) 9_556 ?
C12 C13 1.522(13) . ?
C13 C14 1.376(6) 3_765 ?
C13 N2 1.376(6) 3_765 ?
C10 C9 1.392(9) 9_556 ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
C3 N1 1.3900 . ?
C3 C4 1.3900 . ?
N1 C2 1.3900 . ?
C2 H2 0.9300 . ?
C2 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C4 1.3900 . ?
C4 H4 0.9300 . ?

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
O1 Co1 O2 95.06(18) . . ?
O1 Co1 O2 95.06(18) . 4_556 ?
O1 Co1 O3 90.63(16) . 5_565 ?
O1 Co1 O3 90.63(16) . 2_566 ?
O1 Co1 N1 172.6(5) . . ?
O2 Co1 O2 90.5(4) . 4_556 ?
O2 Co1 N1 86.7(5) . . ?
O2 Co1 N1 92.1(6) 4_556 . ?
O3 Co1 O2 174.3(2) 2_566 . ?
O3 Co1 O2 89.4(3) 5_565 . ?
O3 Co1 O2 174.3(2) 5_565 4_556 ?
O3 Co1 O2 89.4(3) 2_566 4_556 ?
O3 Co1 O3 90.2(4) 5_565 2_566 ?
O3 Co1 N1 87.6(5) 2_566 . ?
O3 Co1 N1 82.2(6) 5_565 . ?
Co1 O1 Co1 120.0 2_566 3_665 ?
Co1 O1 Co1 120.000(1) 3_665 . ?
Co1 O1 Co1 120.000(1) 2_566 . ?
Co1 O1 H1 90.0 2_566 . ?
Co1 O1 H1 90.0 . . ?
Co1 O1 H1 90.0 3_665 . ?
C1 O2 Co1 129.7(5) . . ?
C1 O3 Co1 137.0(5) . 3_665 ?
C8 C7 C8 117.6(10) . 3 ?
C8 C7 C5 120.5(9) . . ?
C8 C7 C5 121.1(9) 3 . ?
O2 C1 O3 128.5(7) . . ?
O2 C1 C9 117.2(7) . . ?
O3 C1 C9 114.3(7) . . ?
C7 C8 C7 122.4(10) . 2_556 ?
C7 C8 H8 118.8 . . ?
C7 C8 H8 118.8 2_556 . ?
C13 C14 H14 121.1 5_675 . ?
C13 C14 H14 121.1 . . ?
C13 C14 C13 117.7(9) 5_675 . ?
C9 C11 H11 119.3 . . ?
C9 C11 C12 121.4(7) . . ?
C12 C11 H11 119.3 . . ?
C11 C9 C1 119.2(6) . . ?
C11 C9 C10 119.6(7) . . ?
C10 C9 C1 121.2(8) . . ?
C11 C12 C11 118.3(10) 9_556 . ?
C11 C12 C13 120.9(5) 9_556 . ?
C11 C12 C13 120.9(5) . . ?
C14 C13 C14 122.3(9) . 3_765 ?
C14 C13 C12 118.9(4) 3_765 . ?
C14 C13 C12 118.9(4) . . ?
N2 C13 C12 118.9(4) 3_765 . ?
C9 C10 C9 119.4(11) 9_556 . ?
C9 C10 H10 120.3 . . ?
C9 C10 H10 120.3 9_556 . ?
N1 C3 H3 120.0 . . ?
N1 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 N1 Co1 122.2(6) . . ?
C2 N1 Co1 116.5(5) . . ?
C2 N1 C3 120.0 . . ?
N1 C2 H2 120.0 . . ?
C5 C2 N1 120.0 . . ?
C5 C2 H2 120.0 . . ?
C2 C5 C7 117.0(7) . . ?
C2 C5 C6 120.0 . . ?
C6 C5 C7 123.0(8) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C4 120.0 . . ?
C4 C6 H6 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C4 C3 120.0 . . ?
C6 C4 H4 120.0 . . ?

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 O2 C1 O3 -8.6(14) . . . . ?
Co1 O2 C1 C9 170.0(5) . . . . ?
Co1 O3 C1 O2 12.2(15) 3_665 . . . ?
Co1 O3 C1 C9 -166.4(6) 3_665 . . . ?
Co1 N1 C2 C5 167.4(15) . . . . ?
O2 C1 C9 C11 -157.2(8) . . . . ?
O2 C1 C9 C10 21.2(11) . . . . ?
O3 C1 C9 C11 21.6(11) . . . . ?
O3 C1 C9 C10 -160.0(7) . . . . ?
C7 C5 C6 C4 177(2) . . . . ?
C1 C9 C10 C9 -176.1(9) . . . 9_556 ?
C8 C7 C8 C7 0.000(0) 3 . . 2_556 ?
C8 C7 C5 C2 25.2(15) 3 . . . ?
C8 C7 C5 C2 -165.2(8) . . . . ?
C8 C7 C5 C6 17(2) . . . . ?
C8 C7 C5 C6 -152.1(10) 3 . . . ?
C11 C9 C10 C9 2.3(6) . . . 9_556 ?
C11 C12 C13 C14 -39.7(4) . . . . ?
C11 C12 C13 C14 140.3(4) 9_556 . . . ?
C11 C12 C13 C14 140.3(4) . . . 3_765 ?
C11 C12 C13 C14 -39.7(4) 9_556 . . 3_765 ?
C11 C12 C13 N2 140.3(4) . . . 3_765 ?
C11 C12 C13 N2 -39.7(4) 9_556 . . 3_765 ?
C9 C11 C12 C11 2.4(6) . . . 9_556 ?
C9 C11 C12 C13 -177.6(6) . . . . ?
C12 C11 C9 C1 173.7(6) . . . . ?
C12 C11 C9 C10 -4.7(11) . . . . ?
C13 C14 C13 C14 0.0 5_675 . . 3_765 ?
C13 C14 C13 C12 180.0 5_675 . . . ?
C13 C14 C13 N2 0.0 5_675 . . 3_765 ?
C3 N1 C2 C5 0.0 . . . . ?
N1 C3 C4 C6 0.0 . . . . ?
N1 C2 C5 C7 -177.4(19) . . . . ?
N1 C2 C5 C6 0.0 . . . . ?
C2 C5 C6 C4 0.0 . . . . ?
C5 C7 C8 C7 -169.9(12) . . . 2_556 ?
C5 C6 C4 C3 0.0 . . . . ?
C4 C3 N1 Co1 -166.7(16) . . . . ?
C4 C3 N1 C2 0.0 . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.816 -0.684 0.279 522.5 145.4 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.177
_oxdiff_exptl_absorpt_empirical_full_min 0.857
