# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2342113'
loop_
_audit_author_name
_audit_author_address
'Lidija Andros Dubraja'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-21 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_shelx               
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE:High Rint value is due to a twinned crystal in with very high 
proportion of completely overlapped reflections, which makes it impossible 
to obtain a better structural model.
;
_vrf_PLAT020_shelx               
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.396 Report
RESPONSE:High Rint value is due to a twinned crystal in with very high 
proportion of completely overlapped reflections, which makes it impossible 
to obtain a better structural model.
;
_vrf_PLAT029_shelx               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.825 Why?  
RESPONSE:  High Rint value is due to a twinned crystal in with very high 
proportion of completely overlapped reflections, which makes it impossible 
to obtain a better structural model.
;
_vrf_PLAT084_shelx               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.51 Report
RESPONSE: High Rint value is due to a twinned crystal in with very high 
proportion of completely overlapped reflections, which makes it impossible 
to obtain a better structural model.
;
_vrf_PLAT201_shelx               
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         15 Report
RESPONSE: Low quality XRD data due to twinned crystal.
;
_vrf_PLAT213_shelx               
;
PROBLEM: Atom C27             has ADP max/min Ratio .....       10.6 prolat
RESPONSE: Low quality XRD data due to twinned crystal.
;
_vrf_PLAT972_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  1.16Ang From Co2            -3.52 eA-3  
RESPONSE: Low quality XRD data due to twinned crystal.
;
_vrf_PLAT973_shelx               
;
PROBLEM: Check Calcd Positive Resid. Density on       Co1       2.23 eA-3  
RESPONSE: Low quality XRD data due to twinned crystal.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'3-oxo-1-azabicyclo[2.2.2]octan-1-ium tetrachloro-cobalt(II)'
_chemical_name_common            '[H-(O)ABCO]2(CoCl4) 293K'
_chemical_formula_moiety         '2(C7 H12 N O), Cl4 Co'
_chemical_formula_sum            'C28 H48 Cl8 Co2 N4 O4'
_chemical_formula_weight         906.16

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   6.5717(5)
_cell_length_b                   13.5034(7)
_cell_length_c                   21.0441(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.322(6)
_cell_angle_gamma                90
_cell_volume                     1867.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3228
_cell_measurement_theta_min      4.1760
_cell_measurement_theta_max      78.4830

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_F_000             932
_exptl_absorpt_coefficient_mu    12.550
_exptl_absorpt_correction_T_min  0.43535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.541
_oxdiff_exptl_absorpt_empirical_full_max 2.491
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            6711
_diffrn_reflns_av_unetI/netI     0.1162
_diffrn_reflns_av_R_equivalents  0.3964
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         7.048
_diffrn_reflns_theta_max         79.417
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.778
_diffrn_measured_fraction_theta_full 0.825
_diffrn_reflns_Laue_measured_fraction_max 0.778
_diffrn_reflns_Laue_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.483
_diffrn_reflns_point_group_measured_fraction_full 0.519
_reflns_number_total             3920
_reflns_number_gt                2454
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.191
_reflns_Friedel_fraction_max     0.162
_reflns_Friedel_fraction_full    0.184

_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       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Mercury (2020)'
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.2000P)²] 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_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3920
_refine_ls_number_parameters     340
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2494
_refine_ls_R_factor_gt           0.1884
_refine_ls_wR_factor_ref         0.5132
_refine_ls_wR_factor_gt          0.4327
_refine_ls_goodness_of_fit_ref   1.969
_refine_ls_restrained_S_all      1.968
_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
C1 C 1.759(3) 0.1611(19) 0.3566(10) 0.026(4) Uiso 1 1 d . . . . .
H1A H 1.806349 0.095121 0.346034 0.032 Uiso 1 1 calc R U . . .
H1B H 1.863253 0.193160 0.382059 0.032 Uiso 1 1 calc R U . . .
C2 C 1.725(3) 0.2195(18) 0.2960(10) 0.022(4) Uiso 1 1 d . . . . .
C3 C 1.505(4) 0.264(2) 0.2944(11) 0.028(5) Uiso 1 1 d . . . . .
H3 H 1.484137 0.304817 0.256490 0.033 Uiso 1 1 calc R U . . .
C4 C 1.363(4) 0.178(2) 0.2949(15) 0.036(7) Uani 1 1 d . . . . .
H4A H 1.381493 0.139976 0.256110 0.043 Uiso 1 1 calc R U . . .
H4B H 1.224126 0.202175 0.295000 0.043 Uiso 1 1 calc R U . . .
C5 C 1.393(6) 0.110(3) 0.3508(15) 0.047(8) Uani 1 1 d . . . . .
H5A H 1.430328 0.044458 0.336357 0.056 Uiso 1 1 calc R U . . .
H5B H 1.267398 0.104954 0.374681 0.056 Uiso 1 1 calc R U . . .
C6 C 1.504(4) 0.261(2) 0.4125(13) 0.038(6) Uiso 1 1 d . . . . .
H6A H 1.376909 0.259313 0.435592 0.045 Uiso 1 1 calc R U . . .
H6B H 1.607221 0.289010 0.440335 0.045 Uiso 1 1 calc R U . . .
C7 C 1.480(4) 0.326(3) 0.3555(18) 0.046(8) Uani 1 1 d . . . . .
H7A H 1.581140 0.378071 0.356611 0.055 Uiso 1 1 calc R U . . .
H7B H 1.346243 0.356349 0.355788 0.055 Uiso 1 1 calc R U . . .
C8 C 0.246(4) 0.414(2) 0.8554(13) 0.036(6) Uani 1 1 d . . . . .
H8A H 0.353796 0.443212 0.881164 0.043 Uiso 1 1 calc R U . . .
H8B H 0.288964 0.348087 0.843668 0.043 Uiso 1 1 calc R U . . .
C9 C 0.222(3) 0.4745(19) 0.7964(11) 0.025(5) Uani 1 1 d . . . . .
C10 C 0.006(4) 0.514(2) 0.7929(12) 0.028(5) Uiso 1 1 d . . . . .
H10 H -0.017478 0.553158 0.754474 0.034 Uiso 1 1 calc R U . . .
C11 C -0.030(4) 0.575(2) 0.8547(14) 0.034(6) Uani 1 1 d . . . . .
H11A H 0.065121 0.630024 0.855875 0.041 Uiso 1 1 calc R U . . .
H11B H -0.166490 0.602885 0.853142 0.041 Uiso 1 1 calc R U . . .
C12 C -0.008(5) 0.519(3) 0.9122(16) 0.049(8) Uiso 1 1 d . . . . .
H12A H -0.136091 0.517761 0.934997 0.059 Uiso 1 1 calc R U . . .
H12B H 0.094087 0.548825 0.939374 0.059 Uiso 1 1 calc R U . . .
C13 C -0.100(4) 0.363(3) 0.8556(13) 0.042(8) Uani 1 1 d . . . . .
H13A H -0.225187 0.360306 0.879808 0.050 Uiso 1 1 calc R U . . .
H13B H -0.062040 0.296293 0.844456 0.050 Uiso 1 1 calc R U . . .
C14 C -0.137(4) 0.421(2) 0.7963(12) 0.032(5) Uiso 1 1 d . . . . .
H14A H -0.278166 0.442733 0.794947 0.038 Uiso 1 1 calc R U . . .
H14B H -0.113956 0.379044 0.759662 0.038 Uiso 1 1 calc R U . . .
C15 C 0.241(3) 0.166(2) 0.6466(12) 0.035(6) Uani 1 1 d . . . . .
H15A H 0.133044 0.197616 0.622345 0.042 Uiso 1 1 calc R U . . .
H15B H 0.197013 0.099854 0.657557 0.042 Uiso 1 1 calc R U . . .
C16 C 0.279(3) 0.2228(18) 0.7047(11) 0.026(5) Uani 1 1 d . . . . .
C17 C 0.500(4) 0.262(2) 0.7051(12) 0.030(5) Uiso 1 1 d . . . . .
H17 H 0.524402 0.301632 0.743386 0.036 Uiso 1 1 calc R U . . .
C18 C 0.639(4) 0.1770(18) 0.7039(15) 0.036(6) Uani 1 1 d . . . . .
H18A H 0.622656 0.139002 0.742658 0.043 Uiso 1 1 calc R U . . .
H18B H 0.778017 0.200785 0.702557 0.043 Uiso 1 1 calc R U . . .
C19 C 0.600(5) 0.111(3) 0.6475(15) 0.041(7) Uiso 1 1 d . . . . .
H19A H 0.553461 0.046257 0.661615 0.050 Uiso 1 1 calc R U . . .
H19B H 0.724219 0.101865 0.623496 0.050 Uiso 1 1 calc R U . . .
C20 C 0.504(5) 0.269(2) 0.5891(11) 0.039(7) Uani 1 1 d . . . . .
H20A H 0.630295 0.267182 0.565585 0.047 Uiso 1 1 calc R U . . .
H20B H 0.401396 0.299994 0.562241 0.047 Uiso 1 1 calc R U . . .
C21 C 0.531(4) 0.327(2) 0.6450(12) 0.028(5) Uiso 1 1 d . . . . .
H21A H 0.434700 0.381042 0.645005 0.033 Uiso 1 1 calc R U . . .
H21B H 0.667382 0.354507 0.645508 0.033 Uiso 1 1 calc R U . . .
C22 C 0.252(4) 0.915(2) 0.8555(13) 0.037(5) Uiso 1 1 d . . . . .
H22A H 0.355550 0.945138 0.882022 0.044 Uiso 1 1 calc R U . . .
H22B H 0.299046 0.849404 0.843466 0.044 Uiso 1 1 calc R U . . .
C23 C 0.221(3) 0.975(2) 0.7980(11) 0.026(5) Uiso 1 1 d . . . . .
C24 C 0.008(4) 1.021(2) 0.7950(13) 0.034(5) Uiso 1 1 d . . . . .
H24 H -0.014918 1.063959 0.757979 0.041 Uiso 1 1 calc R U . . .
C25 C -0.022(4) 1.072(2) 0.8575(14) 0.035(6) Uani 1 1 d . . . . .
H25A H 0.076673 1.125520 0.861254 0.042 Uiso 1 1 calc R U . . .
H25B H -0.156374 1.101731 0.858048 0.042 Uiso 1 1 calc R U . . .
C26 C -0.002(6) 1.012(3) 0.9087(18) 0.054(8) Uiso 1 1 d . . . . .
H26A H -0.130357 1.010151 0.931208 0.064 Uiso 1 1 calc R U . . .
H26B H 0.099445 1.039523 0.937250 0.064 Uiso 1 1 calc R U . . .
C27 C -0.110(5) 0.869(3) 0.8519(14) 0.053(10) Uani 1 1 d . . . . .
H27A H -0.083344 0.800200 0.840640 0.063 Uiso 1 1 calc R U . . .
H27B H -0.234682 0.870327 0.876269 0.063 Uiso 1 1 calc R U . . .
C28 C -0.137(4) 0.924(2) 0.7967(12) 0.036(6) Uani 1 1 d . . . . .
H28A H -0.277887 0.943894 0.793341 0.043 Uiso 1 1 calc R U . . .
H28B H -0.106358 0.882186 0.760238 0.043 Uiso 1 1 calc R U . . .
Cl1 Cl 0.5095(11) 0.6680(7) 1.0949(4) 0.050(2) Uani 1 1 d . . . . .
Cl2 Cl 0.4712(11) 0.6733(7) 0.9057(4) 0.049(2) Uani 1 1 d . . . . .
Cl3 Cl 0.4721(13) 0.8981(7) 1.0019(3) 0.0478(19) Uani 1 1 d . . . . .
Cl4 Cl 0.9286(9) 0.7457(6) 0.9969(3) 0.0386(17) Uani 1 1 d . . . . .
Cl5 Cl 1.0124(11) -0.0814(7) 0.5964(3) 0.0466(18) Uani 1 1 d . . . . .
Cl6 Cl 0.9709(10) -0.0789(6) 0.4056(3) 0.0454(18) Uani 1 1 d . . . . .
Cl7 Cl 1.4292(9) -0.0059(6) 0.4982(4) 0.0404(18) Uani 1 1 d . . . . .
Cl8 Cl 0.9755(13) 0.1479(7) 0.5018(3) 0.049(2) Uani 1 1 d . . . . .
Co1 Co 0.5751(6) 0.7363(4) 0.9993(2) 0.0320(13) Uani 1 1 d . . . . .
Co2 Co 1.0752(6) -0.0151(4) 0.5010(2) 0.0339(14) Uani 1 1 d . . . . .
N1 N 1.566(3) 0.1537(19) 0.3943(10) 0.033(5) Uani 1 1 d . . . . .
H1 H 1.586226 0.112875 0.432336 0.040 Uiso 1 1 calc R U . . .
N2 N 0.059(3) 0.407(2) 0.8947(10) 0.033(5) Uani 1 1 d . . . . .
H2 H 0.082916 0.367375 0.933133 0.040 Uiso 1 1 calc R U . . .
N3 N 0.436(3) 0.1602(17) 0.6055(9) 0.027(4) Uani 1 1 d . . . . .
H3A H 0.410962 0.121675 0.566718 0.032 Uiso 1 1 calc R U . . .
N4 N 0.060(3) 0.9055(18) 0.8922(10) 0.031(4) Uiso 1 1 d . . . . .
H4 H 0.078111 0.864891 0.930362 0.037 Uiso 1 1 calc R U . . .
O1 O 1.855(3) 0.236(2) 0.2619(10) 0.048(6) Uani 1 1 d . . . . .
O2 O 0.347(3) 0.4844(18) 0.7616(11) 0.042(5) Uani 1 1 d . . . . .
O3 O 0.151(3) 0.2386(18) 0.7391(11) 0.043(5) Uani 1 1 d . . . . .
O4 O 0.352(3) 0.9859(19) 0.7605(11) 0.044(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.50(3) . ?
C1 C2 1.51(3) . ?
C2 O1 1.14(3) . ?
C2 C3 1.57(3) . ?
C3 C4 1.49(3) . ?
C3 C7 1.54(5) . ?
C4 C5 1.50(4) . ?
C5 N1 1.57(4) . ?
C6 C7 1.49(4) . ?
C6 N1 1.55(4) . ?
C8 C9 1.49(4) . ?
C8 N2 1.49(3) . ?
C9 O2 1.11(3) . ?
C9 C10 1.52(3) . ?
C10 C11 1.56(3) . ?
C10 C14 1.57(4) . ?
C11 C12 1.44(4) . ?
C12 N2 1.62(4) . ?
C13 N2 1.45(3) . ?
C13 C14 1.49(4) . ?
C15 C16 1.46(4) . ?
C15 N3 1.55(3) . ?
C16 O3 1.13(3) . ?
C16 C17 1.54(3) . ?
C17 C18 1.47(3) . ?
C17 C21 1.55(4) . ?
C18 C19 1.51(4) . ?
C19 N3 1.54(4) . ?
C20 C21 1.42(3) . ?
C20 N3 1.58(3) . ?
C22 C23 1.47(3) . ?
C22 N4 1.49(3) . ?
C23 O4 1.18(3) . ?
C23 C24 1.53(3) . ?
C24 C25 1.50(4) . ?
C24 C28 1.63(4) . ?
C25 C26 1.36(5) . ?
C26 N4 1.53(4) . ?
C27 C28 1.39(4) . ?
C27 N4 1.48(3) . ?
Cl1 Co1 2.257(9) . ?
Cl2 Co1 2.248(8) . ?
Cl3 Co1 2.288(10) . ?
Cl4 Co1 2.327(7) . ?
Cl5 Co2 2.238(9) . ?
Cl6 Co2 2.287(8) . ?
Cl7 Co2 2.331(7) . ?
Cl8 Co2 2.297(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 111.1(18) . . ?
O1 C2 C1 122(2) . . ?
O1 C2 C3 127(2) . . ?
C1 C2 C3 110.4(18) . . ?
C4 C3 C7 110(2) . . ?
C4 C3 C2 106(2) . . ?
C7 C3 C2 107.1(19) . . ?
C3 C4 C5 114(2) . . ?
C4 C5 N1 109(3) . . ?
C7 C6 N1 112(2) . . ?
C6 C7 C3 110(3) . . ?
C9 C8 N2 115(2) . . ?
O2 C9 C8 123(2) . . ?
O2 C9 C10 128(2) . . ?
C8 C9 C10 109(2) . . ?
C9 C10 C11 107(2) . . ?
C9 C10 C14 106(2) . . ?
C11 C10 C14 107(2) . . ?
C12 C11 C10 114(3) . . ?
C11 C12 N2 109(3) . . ?
N2 C13 C14 112(2) . . ?
C13 C14 C10 111(2) . . ?
C16 C15 N3 110.9(19) . . ?
O3 C16 C15 120(2) . . ?
O3 C16 C17 129(2) . . ?
C15 C16 C17 110(2) . . ?
C18 C17 C16 108(2) . . ?
C18 C17 C21 110(2) . . ?
C16 C17 C21 108.6(19) . . ?
C17 C18 C19 112(2) . . ?
C18 C19 N3 108(2) . . ?
C21 C20 N3 111.4(18) . . ?
C20 C21 C17 110(2) . . ?
C23 C22 N4 111(2) . . ?
O4 C23 C22 121(2) . . ?
O4 C23 C24 126(2) . . ?
C22 C23 C24 112(2) . . ?
C25 C24 C23 106(2) . . ?
C25 C24 C28 106(2) . . ?
C23 C24 C28 102(2) . . ?
C26 C25 C24 114(3) . . ?
C25 C26 N4 114(3) . . ?
C28 C27 N4 113(3) . . ?
C27 C28 C24 112(2) . . ?
Cl2 Co1 Cl1 124.6(5) . . ?
Cl2 Co1 Cl3 107.1(3) . . ?
Cl1 Co1 Cl3 108.1(4) . . ?
Cl2 Co1 Cl4 107.5(3) . . ?
Cl1 Co1 Cl4 103.7(3) . . ?
Cl3 Co1 Cl4 104.1(3) . . ?
Cl5 Co2 Cl6 125.5(4) . . ?
Cl5 Co2 Cl8 108.9(4) . . ?
Cl6 Co2 Cl8 106.4(3) . . ?
Cl5 Co2 Cl7 103.5(3) . . ?
Cl6 Co2 Cl7 107.0(4) . . ?
Cl8 Co2 Cl7 103.5(3) . . ?
C1 N1 C6 107(2) . . ?
C1 N1 C5 109(2) . . ?
C6 N1 C5 108(2) . . ?
C13 N2 C8 108(2) . . ?
C13 N2 C12 108(2) . . ?
C8 N2 C12 107(2) . . ?
C19 N3 C15 106(2) . . ?
C19 N3 C20 109(2) . . ?
C15 N3 C20 108(2) . . ?
C27 N4 C22 112(2) . . ?
C27 N4 C26 104(3) . . ?
C22 N4 C26 105(2) . . ?

_refine_diff_density_max         3.527
_refine_diff_density_min         -3.505
_refine_diff_density_rms         0.582



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2342115'
loop_
_audit_author_name
_audit_author_address
'Lidija Andros Dubraja'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-21 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'3-oxo-1-azabicyclo[2.2.2]octan-1-ium tetrachloro-cobalt(II)'
_chemical_name_common            '[H-(O)ABCO]2(CoCl4)xH2O'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H12 N O), Cl4 Co, H2 O'
_chemical_formula_sum            'C14 H26 Cl4 Co N2 O3'
_chemical_formula_weight         471.10

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'
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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P c 21 n'
_space_group_name_Hall           'P -2n -2ac'

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

_cell_length_a                   14.2651(2)
_cell_length_b                   9.0392(2)
_cell_length_c                   15.7057(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2025.17(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6677
_cell_measurement_theta_min      4.1650
_cell_measurement_theta_max      7.4440

_exptl_crystal_description       stick
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             972
_exptl_absorpt_coefficient_mu    11.632
_exptl_absorpt_correction_T_min  0.49749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.582
_oxdiff_exptl_absorpt_empirical_full_max 1.669
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            9146
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.187
_diffrn_reflns_theta_max         88.168
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.656
_diffrn_reflns_point_group_measured_fraction_full 0.736
_reflns_number_total             3031
_reflns_number_gt                2917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.368
_reflns_Friedel_fraction_max     0.377
_reflns_Friedel_fraction_full    0.446

_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       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_structure_solution    'SIR-2019 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Mercury (2020)'
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0856P)²+0.1950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.010(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3031
_refine_ls_number_parameters     225
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.099
_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
C1 C 0.9821(3) 0.1101(6) 0.6720(3) 0.0472(10) Uani 1 1 d . . . . .
H1A H 0.934905 0.157372 0.707185 0.057 Uiso 1 1 calc R U . . .
H1B H 0.971885 0.004090 0.674241 0.057 Uiso 1 1 calc R U . . .
C2 C 0.9716(3) 0.1678(6) 0.5733(3) 0.0482(10) Uani 1 1 d . . . . .
C3 C 1.0528(4) 0.2338(7) 0.5359(3) 0.0540(12) Uani 1 1 d . . . . .
H3 H 1.042470 0.269914 0.477815 0.065 Uiso 1 1 calc R U . . .
C4 C 1.0779(4) 0.3586(7) 0.6007(4) 0.0667(15) Uani 1 1 d . . . . .
H4A H 1.031227 0.436250 0.596099 0.080 Uiso 1 1 calc R U . . .
H4B H 1.137834 0.400820 0.584639 0.080 Uiso 1 1 calc R U . . .
C5 C 1.0840(4) 0.3051(6) 0.7021(4) 0.0539(11) Uani 1 1 d . . . . .
H5A H 1.144555 0.330595 0.725926 0.065 Uiso 1 1 calc R U . . .
H5B H 1.035620 0.353651 0.735339 0.065 Uiso 1 1 calc R U . . .
C6 C 1.1337(3) 0.0628(7) 0.6429(4) 0.0528(12) Uani 1 1 d . . . . .
H6A H 1.122193 -0.042577 0.647814 0.063 Uiso 1 1 calc R U . . .
H6B H 1.198186 0.080693 0.659629 0.063 Uiso 1 1 calc R U . . .
C7 C 1.1206(3) 0.1124(8) 0.5411(3) 0.0596(15) Uani 1 1 d . . . . .
H7A H 1.180376 0.143995 0.517884 0.072 Uiso 1 1 calc R U . . .
H7B H 1.098531 0.028769 0.507988 0.072 Uiso 1 1 calc R U . . .
C8 C 0.9170(3) 0.2943(7) 1.0097(4) 0.0572(13) Uani 1 1 d . . . . .
H8A H 0.963001 0.275544 1.053948 0.069 Uiso 1 1 calc R U . . .
H8B H 0.928817 0.392038 0.986571 0.069 Uiso 1 1 calc R U . . .
C9 C 0.9274(3) 0.1763(7) 0.9378(3) 0.0556(13) Uani 1 1 d . . . . .
C10 C 0.8507(5) 0.0752(7) 0.9322(4) 0.0621(14) Uani 1 1 d . . . . .
H10 H 0.863899 -0.007540 0.893747 0.074 Uiso 1 1 calc R U . . .
C11 C 0.8345(6) 0.0205(7) 1.0313(4) 0.0728(18) Uani 1 1 d . . . . .
H11A H 0.784778 -0.052651 1.032085 0.087 Uiso 1 1 calc R U . . .
H11B H 0.891291 -0.027351 1.051129 0.087 Uiso 1 1 calc R U . . .
C12 C 0.8086(3) 0.1475(7) 1.0947(3) 0.0523(11) Uani 1 1 d . . . . .
H12A H 0.743318 0.141209 1.111528 0.063 Uiso 1 1 calc R U . . .
H12B H 0.847531 0.143054 1.145340 0.063 Uiso 1 1 calc R U . . .
C13 C 0.7682(3) 0.3045(6) 0.9618(4) 0.0621(14) Uani 1 1 d . . . . .
H13A H 0.702994 0.317923 0.977373 0.075 Uiso 1 1 calc R U . . .
H13B H 0.788227 0.392666 0.931611 0.075 Uiso 1 1 calc R U . . .
C14 C 0.7758(4) 0.1700(9) 0.9007(3) 0.0691(16) Uani 1 1 d . . . . .
H14A H 0.717066 0.116104 0.899498 0.083 Uiso 1 1 calc R U . . .
H14B H 0.789972 0.203275 0.843409 0.083 Uiso 1 1 calc R U . . .
N1 N 1.0703(2) 0.1427(5) 0.7035(2) 0.0403(7) Uani 1 1 d . . . . .
H1 H 1.077650 0.104032 0.761433 0.048 Uiso 1 1 calc R U . . .
N2 N 0.8274(2) 0.2896(4) 1.0446(3) 0.0477(9) Uani 1 1 d . . . . .
H2 H 0.817262 0.375963 1.081140 0.057 Uiso 1 1 calc R U . . .
O1 O 0.9048(2) 0.1586(7) 0.5330(3) 0.0791(14) Uani 1 1 d . . . . .
O2 O 0.9912(3) 0.1680(8) 0.8897(3) 0.0891(18) Uani 1 1 d . . . . .
O3 O 0.6672(2) 0.5697(4) 0.6308(2) 0.0515(8) Uani 1 1 d D . . . .
Cl1 Cl 1.02933(8) 0.71610(18) 0.73029(10) 0.0618(3) Uani 1 1 d . . . . .
Cl2 Cl 0.86830(9) 0.67167(16) 0.91806(7) 0.0554(3) Uani 1 1 d . . . . .
Cl3 Cl 0.85034(8) 0.43488(14) 0.70916(9) 0.0560(3) Uani 1 1 d . . . . .
Cl4 Cl 0.80644(8) 0.83150(14) 0.68900(9) 0.0587(3) Uani 1 1 d D . . . .
Co1 Co 0.89111(4) 0.66309(9) 0.76054(4) 0.03750(19) Uani 1 1 d . . . . .
H3A H 0.657(6) 0.621(9) 0.577(3) 0.09(3) Uiso 1 1 d D . . . .
H3B H 0.722(3) 0.540(3) 0.639(7) 0.29(11) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.383(5) . ?
C1 C2 1.642(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O1 1.147(5) . ?
C2 C3 1.429(7) . ?
C3 C7 1.465(8) . ?
C3 C4 1.561(9) . ?
C3 H3 0.9800 . ?
C4 C5 1.666(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.481(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.498(6) . ?
C6 C7 1.672(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.392(6) . ?
C8 C9 1.561(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O2 1.186(6) . ?
C9 C10 1.427(9) . ?
C10 C14 1.456(10) . ?
C10 C11 1.649(9) . ?
C10 H10 0.9800 . ?
C11 C12 1.564(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.530(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.553(10) . ?
C13 N2 1.555(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N1 H1 0.9800 . ?
N2 H2 0.9800 . ?
O3 H3A 0.98(2) . ?
O3 H3B 0.83(2) . ?
Cl1 Co1 2.0840(13) . ?
Cl2 Co1 2.4964(12) . ?
Cl3 Co1 2.2902(15) . ?
Cl4 Co1 2.2447(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 110.7(4) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C3 118.5(5) . . ?
O1 C2 C1 125.0(5) . . ?
C3 C2 C1 116.5(4) . . ?
C2 C3 C7 101.6(5) . . ?
C2 C3 C4 102.7(4) . . ?
C7 C3 C4 110.7(5) . . ?
C2 C3 H3 113.6 . . ?
C7 C3 H3 113.6 . . ?
C4 C3 H3 113.6 . . ?
C3 C4 C5 115.2(4) . . ?
C3 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C5 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
N1 C5 C4 107.2(4) . . ?
N1 C5 H5A 110.3 . . ?
C4 C5 H5A 110.3 . . ?
N1 C5 H5B 110.3 . . ?
C4 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
N1 C6 C7 114.3(4) . . ?
N1 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
N1 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C3 C7 C6 109.1(4) . . ?
C3 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
C3 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N2 C8 C9 110.5(4) . . ?
N2 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O2 C9 C10 120.5(6) . . ?
O2 C9 C8 125.3(6) . . ?
C10 C9 C8 114.2(4) . . ?
C9 C10 C14 101.9(5) . . ?
C9 C10 C11 104.0(5) . . ?
C14 C10 C11 113.2(5) . . ?
C9 C10 H10 112.3 . . ?
C14 C10 H10 112.3 . . ?
C11 C10 H10 112.3 . . ?
C12 C11 C10 114.5(5) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
N2 C12 C11 104.3(4) . . ?
N2 C12 H12A 110.9 . . ?
C11 C12 H12A 110.9 . . ?
N2 C12 H12B 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C14 C13 N2 114.2(4) . . ?
C14 C13 H13A 108.7 . . ?
N2 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
N2 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C10 C14 C13 107.6(4) . . ?
C10 C14 H14A 110.2 . . ?
C13 C14 H14A 110.2 . . ?
C10 C14 H14B 110.2 . . ?
C13 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C1 N1 C5 109.0(4) . . ?
C1 N1 C6 102.7(4) . . ?
C5 N1 C6 112.8(4) . . ?
C1 N1 H1 110.7 . . ?
C5 N1 H1 110.7 . . ?
C6 N1 H1 110.7 . . ?
C8 N2 C12 112.9(4) . . ?
C8 N2 C13 99.6(4) . . ?
C12 N2 C13 114.1(4) . . ?
C8 N2 H2 109.9 . . ?
C12 N2 H2 109.9 . . ?
C13 N2 H2 109.9 . . ?
H3A O3 H3B 114(6) . . ?
Cl1 Co1 Cl4 103.83(6) . . ?
Cl1 Co1 Cl3 111.53(6) . . ?
Cl4 Co1 Cl3 107.33(6) . . ?
Cl1 Co1 Cl2 110.01(6) . . ?
Cl4 Co1 Cl2 113.88(6) . . ?
Cl3 Co1 Cl2 110.12(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 -177.7(6) . . . . ?
N1 C1 C2 C3 2.6(6) . . . . ?
O1 C2 C3 C7 -119.9(6) . . . . ?
C1 C2 C3 C7 59.9(6) . . . . ?
O1 C2 C3 C4 125.5(6) . . . . ?
C1 C2 C3 C4 -54.7(6) . . . . ?
C2 C3 C4 C5 50.2(6) . . . . ?
C7 C3 C4 C5 -57.5(6) . . . . ?
C3 C4 C5 N1 4.4(6) . . . . ?
C2 C3 C7 C6 -58.7(6) . . . . ?
C4 C3 C7 C6 49.7(6) . . . . ?
N1 C6 C7 C3 4.2(7) . . . . ?
N2 C8 C9 O2 169.5(5) . . . . ?
N2 C8 C9 C10 -9.5(7) . . . . ?
O2 C9 C10 C14 -109.3(6) . . . . ?
C8 C9 C10 C14 69.7(6) . . . . ?
O2 C9 C10 C11 132.8(5) . . . . ?
C8 C9 C10 C11 -48.2(6) . . . . ?
C9 C10 C11 C12 61.0(7) . . . . ?
C14 C10 C11 C12 -48.8(8) . . . . ?
C10 C11 C12 N2 -11.5(7) . . . . ?
C9 C10 C14 C13 -54.0(5) . . . . ?
C11 C10 C14 C13 57.0(7) . . . . ?
N2 C13 C14 C10 -9.7(6) . . . . ?
C2 C1 N1 C5 60.8(5) . . . . ?
C2 C1 N1 C6 -59.1(5) . . . . ?
C4 C5 N1 C1 -62.1(5) . . . . ?
C4 C5 N1 C6 51.3(5) . . . . ?
C7 C6 N1 C1 57.6(6) . . . . ?
C7 C6 N1 C5 -59.6(5) . . . . ?
C9 C8 N2 C12 68.2(6) . . . . ?
C9 C8 N2 C13 -53.2(5) . . . . ?
C11 C12 N2 C8 -52.8(6) . . . . ?
C11 C12 N2 C13 60.0(5) . . . . ?
C14 C13 N2 C8 67.0(5) . . . . ?
C14 C13 N2 C12 -53.5(5) . . . . ?

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.080



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2342114'
loop_
_audit_author_name
_audit_author_address
'Lidija Andros Dubraja'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2024-03-21 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'3-oxo-1-azabicyclo[2.2.2]octan-1-ium tetrachloro-cobalt(II)'
_chemical_name_common            '[H-(O)ABCO]2(CoCl4) 100K'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H12 N O), Cl4 Co'
_chemical_formula_sum            'C14 H24 Cl4 Co N2 O2'
_chemical_formula_weight         453.08

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   6.93160(10)
_cell_length_b                   12.3079(2)
_cell_length_c                   11.5102(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.751(2)
_cell_angle_gamma                90
_cell_volume                     945.10(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5226
_cell_measurement_theta_min      3.9480
_cell_measurement_theta_max      78.8570

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             466
_exptl_absorpt_coefficient_mu    12.398
_exptl_absorpt_correction_T_min  0.49574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.445
_oxdiff_exptl_absorpt_empirical_full_max 3.188
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      100(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            6761
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.990
_diffrn_reflns_theta_max         79.671
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.763
_diffrn_reflns_point_group_measured_fraction_full 0.811
_reflns_number_total             3138
_reflns_number_gt                2988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.499
_reflns_Friedel_fraction_max     0.533
_reflns_Friedel_fraction_full    0.606

_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       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_structure_solution    'SIR-2019 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Mercury (2020)'
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0670P)²+0.1906P] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0022(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.030(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3138
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.58877(9) 0.11822(6) 0.27490(6) 0.0396(2) Uani 1 1 d . . . . .
Cl2 Cl 0.60118(18) 0.10162(11) 0.08071(10) 0.0552(3) Uani 1 1 d . . . . .
Cl3 Cl 0.61970(16) 0.29333(9) 0.34627(9) 0.0460(3) Uani 1 1 d . . . . .
Cl4 Cl 0.27227(15) 0.06709(12) 0.27565(9) 0.0543(3) Uani 1 1 d . . . . .
Cl5 Cl 0.8022(2) 0.02148(11) 0.42091(16) 0.0756(5) Uani 1 1 d . . . . .
O14 O 0.8251(5) 0.1044(4) 0.8077(3) 0.0607(9) Uani 1 1 d . . . . .
N15 N 0.6309(5) 0.7014(3) 0.4649(3) 0.0403(8) Uani 1 1 d . . . . .
H15 H 0.582149 0.699905 0.537259 0.048 Uiso 1 1 calc R U . . .
N9 N 1.1426(5) -0.0675(3) 1.0279(3) 0.0385(7) Uani 1 1 d . . . . .
H9 H 1.259201 -0.058328 1.097830 0.046 Uiso 1 1 calc R U . . .
C11 C 0.8959(6) 0.0263(4) 0.8685(4) 0.0409(9) Uani 1 1 d . . . . .
O23 O 0.4980(6) 0.8302(3) 0.1763(3) 0.0591(9) Uani 1 1 d . . . . .
C13 C 0.9850(8) -0.1284(4) 1.0660(4) 0.0515(11) Uani 1 1 d . . . . .
H13A H 0.953215 -0.090995 1.132635 0.062 Uiso 1 1 calc R U . . .
H13B H 1.033883 -0.200417 1.093315 0.062 Uiso 1 1 calc R U . . .
C16 C 0.6249(8) 0.5878(4) 0.4162(4) 0.0486(10) Uani 1 1 d . . . . .
H16A H 0.489648 0.559135 0.398835 0.058 Uiso 1 1 calc R U . . .
H16B H 0.712634 0.540926 0.475314 0.058 Uiso 1 1 calc R U . . .
C19 C 0.5766(6) 0.7778(4) 0.2643(4) 0.0394(9) Uani 1 1 d . . . . .
C17 C 0.6938(8) 0.5913(4) 0.3004(4) 0.0483(10) Uani 1 1 d . . . . .
H17A H 0.805861 0.542165 0.307837 0.058 Uiso 1 1 calc R U . . .
H17B H 0.585363 0.567730 0.232453 0.058 Uiso 1 1 calc R U . . .
C8 C 1.2061(6) -0.1282(5) 0.9309(4) 0.0506(11) Uani 1 1 d . . . . .
H8A H 1.266578 -0.196976 0.962412 0.061 Uiso 1 1 calc R U . . .
H8B H 1.304586 -0.086087 0.904464 0.061 Uiso 1 1 calc R U . . .
C18 C 0.7565(6) 0.7064(4) 0.2779(4) 0.0411(9) Uani 1 1 d . . . . .
H18 H 0.804379 0.709121 0.205280 0.049 Uiso 1 1 calc R U . . .
C10 C 1.0662(6) 0.0417(4) 0.9815(4) 0.0394(9) Uani 1 1 d . . . . .
H10A H 1.172567 0.083824 0.963342 0.047 Uiso 1 1 calc R U . . .
H10B H 1.019104 0.080404 1.041984 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7962(7) -0.1379(4) 0.9601(5) 0.0510(11) Uani 1 1 d . . . . .
H12A H 0.686506 -0.098897 0.978616 0.061 Uiso 1 1 calc R U . . .
H12B H 0.757794 -0.213550 0.946449 0.061 Uiso 1 1 calc R U . . .
C7 C 1.0221(7) -0.1483(4) 0.8245(4) 0.0473(10) Uani 1 1 d . . . . .
H7A H 0.995386 -0.225682 0.815703 0.057 Uiso 1 1 calc R U . . .
H7B H 1.047705 -0.121966 0.750672 0.057 Uiso 1 1 calc R U . . .
C20 C 0.4990(6) 0.7740(4) 0.3746(4) 0.0442(10) Uani 1 1 d . . . . .
H20A H 0.499138 0.846418 0.407891 0.053 Uiso 1 1 calc R U . . .
H20B H 0.362660 0.746684 0.353170 0.053 Uiso 1 1 calc R U . . .
C21 C 0.8418(6) 0.7436(4) 0.4995(4) 0.0421(9) Uani 1 1 d . . . . .
H21A H 0.925690 0.697752 0.561472 0.051 Uiso 1 1 calc R U . . .
H21B H 0.844713 0.816692 0.531453 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8390(6) -0.0894(4) 0.8457(4) 0.0447(10) Uani 1 1 d . . . . .
H6 H 0.722191 -0.097020 0.775650 0.054 Uiso 1 1 calc R U . . .
C22 C 0.9206(6) 0.7442(4) 0.3891(4) 0.0461(10) Uani 1 1 d . . . . .
H22A H 1.035578 0.696226 0.402179 0.055 Uiso 1 1 calc R U . . .
H22B H 0.963604 0.816963 0.375574 0.055 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 Cl5 2.2541(14) . ?
Co1 Cl2 2.2692(12) . ?
Co1 Cl4 2.2846(12) . ?
Co1 Cl3 2.2957(13) . ?
O14 C11 1.211(6) . ?
N15 C20 1.483(6) . ?
N15 C21 1.500(5) . ?
N15 C16 1.504(6) . ?
N9 C13 1.486(6) . ?
N9 C10 1.489(6) . ?
N9 C8 1.505(6) . ?
C11 C6 1.483(7) . ?
C11 C10 1.512(5) . ?
O23 C19 1.200(5) . ?
C13 C12 1.531(7) . ?
C16 C17 1.534(7) . ?
C19 C18 1.499(6) . ?
C19 C20 1.508(6) . ?
C17 C18 1.524(7) . ?
C8 C7 1.529(6) . ?
C18 C22 1.536(6) . ?
C12 C6 1.546(7) . ?
C7 C6 1.538(7) . ?
C21 C22 1.512(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
Cl5 Co1 Cl2 119.61(7) . . ?
Cl5 Co1 Cl4 106.75(6) . . ?
Cl2 Co1 Cl4 105.79(5) . . ?
Cl5 Co1 Cl3 104.50(5) . . ?
Cl2 Co1 Cl3 114.34(5) . . ?
Cl4 Co1 Cl3 104.70(5) . . ?
C20 N15 C21 110.4(3) . . ?
C20 N15 C16 110.4(3) . . ?
C21 N15 C16 110.3(4) . . ?
C13 N9 C10 110.0(4) . . ?
C13 N9 C8 110.8(4) . . ?
C10 N9 C8 109.2(3) . . ?
O14 C11 C6 127.8(4) . . ?
O14 C11 C10 119.8(5) . . ?
C6 C11 C10 112.3(4) . . ?
N9 C13 C12 110.0(4) . . ?
N15 C16 C17 108.3(4) . . ?
O23 C19 C18 125.3(4) . . ?
O23 C19 C20 122.9(4) . . ?
C18 C19 C20 111.7(3) . . ?
C18 C17 C16 110.1(4) . . ?
N9 C8 C7 109.1(3) . . ?
C19 C18 C17 107.1(4) . . ?
C19 C18 C22 108.4(4) . . ?
C17 C18 C22 108.7(4) . . ?
N9 C10 C11 108.3(3) . . ?
C13 C12 C6 109.2(4) . . ?
C8 C7 C6 110.0(3) . . ?
N15 C20 C19 108.4(3) . . ?
N15 C21 C22 109.1(3) . . ?
C11 C6 C7 106.8(4) . . ?
C11 C6 C12 108.8(4) . . ?
C7 C6 C12 108.1(4) . . ?
C21 C22 C18 110.1(3) . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.066



