# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 
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data_Cu-deox2-h2o
_database_code_depnum_ccdc_archive 'CCDC 1549267'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
 
;
_chemical_formula_moiety         'C16 H24 Cu O11'
_chemical_formula_sum            'C16 H24 Cu O11'
_chemical_formula_weight         455.89

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.6672(5)
_cell_length_b                   24.3174(15)
_cell_length_c                   10.4133(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.6960(10)
_cell_angle_gamma                90
_cell_volume                     2078.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3375
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      21.49

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.104
_shelx_estimated_absorpt_T_min   0.567
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            16544
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.675
_diffrn_reflns_theta_max         28.807
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5068
_reflns_number_gt                3284
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SHELXTL-NT 6.1 (Bruker)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0666P)²+0.5879P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5068
_refine_ls_number_parameters     279
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_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
Cu1 Cu 0.74796(4) 0.95528(2) 1.01075(4) 0.05508(16) Uani 1 1 d . . . . .
O1 O 1.0138(3) 0.93704(10) 1.1360(2) 0.0634(6) Uani 1 1 d . . . . .
H1A H 1.068911 0.934638 1.085273 0.095 Uiso 1 1 calc R U . . .
H1B H 1.042(5) 0.9594(16) 1.190(4) 0.095 Uiso 1 1 d . U . . .
C11 C 0.7365(4) 1.12539(13) 1.1009(3) 0.0631(8) Uani 1 1 d . . . . .
O11A O 0.7169(4) 1.15670(10) 1.1828(3) 0.0996(9) Uani 1 1 d . . . . .
O11B O 0.7819(3) 1.13951(9) 0.9965(2) 0.0709(6) Uani 1 1 d . . . . .
C12 C 0.7119(3) 1.06342(12) 1.1055(3) 0.0538(7) Uani 1 1 d . . . . .
O12 O 0.7610(2) 1.03442(8) 1.0226(2) 0.0591(5) Uani 1 1 d . . . . .
C13 C 0.6413(4) 1.04543(12) 1.1974(3) 0.0591(8) Uani 1 1 d . . . . .
H13 H 0.610042 1.071208 1.250297 0.071 Uiso 1 1 calc R U . . .
C14 C 0.6136(3) 0.98885(12) 1.2155(3) 0.0544(7) Uani 1 1 d . . . . .
O14A O 0.6494(3) 0.94984(8) 1.1536(2) 0.0611(6) Uani 1 1 d . . . . .
O14B O 0.5432(3) 0.97941(9) 1.3088(2) 0.0626(5) Uani 1 1 d . . . . .
C15 C 0.8164(5) 1.19775(14) 0.9863(4) 0.0864(11) Uani 1 1 d D . . . .
H15A H 0.908970 1.208897 1.062658 0.104 Uiso 0.735(18) 1 calc R U P A 1
H15B H 0.723007 1.219805 0.986049 0.104 Uiso 0.735(18) 1 calc R U P A 1
H15C H 0.932898 1.203728 1.011063 0.104 Uiso 0.265(18) 1 calc R U P A 2
H15D H 0.774891 1.219154 1.046718 0.104 Uiso 0.265(18) 1 calc R U P A 2
C16A C 0.8532(16) 1.2055(3) 0.8556(7) 0.098(3) Uani 0.735(18) 1 d D . P A 1
H16A H 0.876562 1.243511 0.845400 0.146 Uiso 0.735(18) 1 calc R U P A 1
H16B H 0.945735 1.183492 0.857121 0.146 Uiso 0.735(18) 1 calc R U P A 1
H16C H 0.760624 1.194350 0.780863 0.146 Uiso 0.735(18) 1 calc R U P A 1
C16B C 0.733(4) 1.2147(7) 0.8411(10) 0.092(8) Uani 0.265(18) 1 d D . P A 2
H16D H 0.753628 1.253023 0.830626 0.138 Uiso 0.265(18) 1 calc R U P A 2
H16E H 0.775528 1.193320 0.782361 0.138 Uiso 0.265(18) 1 calc R U P A 2
H16F H 0.618236 1.208676 0.817854 0.138 Uiso 0.265(18) 1 calc R U P A 2
C17 C 0.4931(4) 0.92370(14) 1.3229(4) 0.0696(9) Uani 1 1 d . . . . .
H17A H 0.585698 0.899023 1.342662 0.083 Uiso 1 1 calc R U . . .
H17B H 0.411883 0.911721 1.239639 0.083 Uiso 1 1 calc R U . . .
C18 C 0.4240(5) 0.92337(15) 1.4359(4) 0.0822(11) Uani 1 1 d . . . . .
H18A H 0.330545 0.947071 1.414003 0.123 Uiso 1 1 calc R U . . .
H18B H 0.504474 0.936203 1.517119 0.123 Uiso 1 1 calc R U . . .
H18C H 0.392096 0.886607 1.449717 0.123 Uiso 1 1 calc R U . . .
O19 O 0.8017(3) 0.96033(8) 0.8461(2) 0.0590(5) Uani 1 1 d . . . . .
C21 C 0.8898(4) 0.93602(14) 0.6646(3) 0.0564(7) Uani 1 1 d . . . . .
O21A O 0.9268(3) 0.98187(10) 0.6492(2) 0.0769(7) Uani 1 1 d . . . . .
O21B O 0.9049(3) 0.89395(9) 0.5893(2) 0.0726(7) Uani 1 1 d . . . . .
C22 C 0.8235(3) 0.91938(12) 0.7782(3) 0.0518(7) Uani 1 1 d . . . . .
C23 C 0.7955(4) 0.86518(12) 0.7975(3) 0.0638(8) Uani 1 1 d . . . . .
H23 H 0.816363 0.839084 0.739846 0.077 Uiso 1 1 calc R U . . .
C24 C 0.7358(4) 0.84741(12) 0.9021(3) 0.0617(8) Uani 1 1 d . . . . .
O24A O 0.7051(3) 0.87639(9) 0.9874(2) 0.0642(6) Uani 1 1 d . . . . .
O24B O 0.7144(4) 0.79319(9) 0.9044(3) 0.0885(8) Uani 1 1 d . . . . .
C25 C 0.9773(5) 0.90686(14) 0.4840(3) 0.0794(10) Uani 1 1 d D . . . .
H25A H 1.092273 0.914987 0.524683 0.095 Uiso 0.46(5) 1 calc R U P B 3
H25B H 0.924358 0.938780 0.432711 0.095 Uiso 0.46(5) 1 calc R U P B 3
H25C H 1.072522 0.930034 0.519987 0.095 Uiso 0.54(5) 1 calc R U P B 4
H25D H 0.899432 0.925863 0.408976 0.095 Uiso 0.54(5) 1 calc R U P B 4
C26A C 0.955(4) 0.8576(7) 0.392(2) 0.090(5) Uani 0.46(5) 1 d D . P B 3
H26A H 1.001897 0.865193 0.321502 0.135 Uiso 0.46(5) 1 calc R U P B 3
H26B H 1.008314 0.826286 0.443146 0.135 Uiso 0.46(5) 1 calc R U P B 3
H26C H 0.841040 0.849989 0.351525 0.135 Uiso 0.46(5) 1 calc R U P B 3
C26B C 1.024(4) 0.8524(5) 0.438(3) 0.095(5) Uani 0.54(5) 1 d D . P B 4
H26D H 1.072676 0.858425 0.368124 0.142 Uiso 0.54(5) 1 calc R U P B 4
H26E H 1.100839 0.834053 0.513230 0.142 Uiso 0.54(5) 1 calc R U P B 4
H26F H 0.928720 0.829906 0.402842 0.142 Uiso 0.54(5) 1 calc R U P B 4
C27 C 0.6613(7) 0.77303(15) 1.0176(5) 0.1207(18) Uani 1 1 d D . . . .
H27A H 0.585463 0.798682 1.036242 0.145 Uiso 1 1 calc R U . . .
H27B H 0.754103 0.768642 1.099045 0.145 Uiso 1 1 calc R U . . .
C28 C 0.5810(7) 0.71910(18) 0.9728(6) 0.147(2) Uani 1 1 d D . . . .
H28A H 0.497012 0.723460 0.887023 0.220 Uiso 1 1 calc R U . . .
H28B H 0.533912 0.705924 1.038785 0.220 Uiso 1 1 calc R U . . .
H28C H 0.660220 0.693133 0.963602 0.220 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
Cu1 O19 1.919(2) . ?
Cu1 O12 1.930(2) . ?
Cu1 O14A 1.9425(19) . ?
Cu1 O24A 1.954(2) . ?
Cu1 O1 2.298(2) . ?
O1 H1A 0.8200 . ?
O1 H1B 0.76(4) . ?
C11 O11A 1.195(4) . ?
C11 O11B 1.315(4) . ?
C11 C12 1.525(4) . ?
O11B C15 1.458(4) . ?
C12 O12 1.288(3) . ?
C12 C13 1.363(4) . ?
C13 C14 1.420(4) . ?
C13 H13 0.9300 . ?
C14 O14A 1.241(3) . ?
C14 O14B 1.323(3) . ?
O14B C17 1.444(4) . ?
C15 C16A 1.506(3) . ?
C15 C16B 1.509(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17 C18 1.481(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O19 C22 1.270(3) . ?
C21 O21A 1.185(4) . ?
C21 O21B 1.321(4) . ?
C21 C22 1.527(4) . ?
O21B C25 1.462(3) . ?
C22 C23 1.366(4) . ?
C23 C24 1.415(4) . ?
C23 H23 0.9300 . ?
C24 O24A 1.228(4) . ?
C24 O24B 1.333(3) . ?
O24B C27 1.479(5) . ?
C25 C26B 1.509(3) . ?
C25 C26A 1.509(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C25 H25D 0.9700 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C26B H26D 0.9600 . ?
C26B H26E 0.9600 . ?
C26B H26F 0.9600 . ?
C27 C28 1.488(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O19 Cu1 O12 88.12(8) . . ?
O19 Cu1 O14A 168.65(9) . . ?
O12 Cu1 O14A 92.87(8) . . ?
O19 Cu1 O24A 92.45(8) . . ?
O12 Cu1 O24A 172.72(9) . . ?
O14A Cu1 O24A 85.16(8) . . ?
O19 Cu1 O1 91.90(9) . . ?
O12 Cu1 O1 97.40(9) . . ?
O14A Cu1 O1 99.17(9) . . ?
O24A Cu1 O1 89.83(9) . . ?
Cu1 O1 H1A 109.5 . . ?
Cu1 O1 H1B 108(3) . . ?
H1A O1 H1B 113.8 . . ?
O11A C11 O11B 124.9(3) . . ?
O11A C11 C12 123.6(3) . . ?
O11B C11 C12 111.5(3) . . ?
C11 O11B C15 115.9(3) . . ?
O12 C12 C13 127.9(3) . . ?
O12 C12 C11 116.2(3) . . ?
C13 C12 C11 116.0(3) . . ?
C12 O12 Cu1 124.33(19) . . ?
C12 C13 C14 122.5(3) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
O14A C14 O14B 120.0(3) . . ?
O14A C14 C13 126.2(3) . . ?
O14B C14 C13 113.8(3) . . ?
C14 O14A Cu1 126.19(19) . . ?
C14 O14B C17 117.5(2) . . ?
O11B C15 C16A 107.1(3) . . ?
O11B C15 C16B 107.2(7) . . ?
O11B C15 H15A 110.3 . . ?
C16A C15 H15A 110.3 . . ?
O11B C15 H15B 110.3 . . ?
C16A C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
O11B C15 H15C 110.3 . . ?
C16B C15 H15C 110.3 . . ?
O11B C15 H15D 110.3 . . ?
C16B C15 H15D 110.3 . . ?
H15C C15 H15D 108.5 . . ?
C15 C16A H16A 109.5 . . ?
C15 C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C15 C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C15 C16B H16D 109.5 . . ?
C15 C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15 C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
O14B C17 C18 107.3(3) . . ?
O14B C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
O14B C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 O19 Cu1 124.68(18) . . ?
O21A C21 O21B 124.5(3) . . ?
O21A C21 C22 122.6(3) . . ?
O21B C21 C22 112.9(3) . . ?
C21 O21B C25 115.3(2) . . ?
O19 C22 C23 127.6(3) . . ?
O19 C22 C21 112.6(2) . . ?
C23 C22 C21 119.9(3) . . ?
C22 C23 C24 122.2(3) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
O24A C24 O24B 119.4(3) . . ?
O24A C24 C23 126.8(3) . . ?
O24B C24 C23 113.8(3) . . ?
C24 O24A Cu1 125.20(19) . . ?
C24 O24B C27 115.0(3) . . ?
O21B C25 C26B 105.9(9) . . ?
O21B C25 C26A 108.1(10) . . ?
O21B C25 H25A 110.1 . . ?
C26A C25 H25A 110.1 . . ?
O21B C25 H25B 110.1 . . ?
C26A C25 H25B 110.1 . . ?
H25A C25 H25B 108.4 . . ?
O21B C25 H25C 110.6 . . ?
C26B C25 H25C 110.6 . . ?
O21B C25 H25D 110.6 . . ?
C26B C25 H25D 110.6 . . ?
H25C C25 H25D 108.7 . . ?
C25 C26A H26A 109.5 . . ?
C25 C26A H26B 109.5 . . ?
H26A C26A H26B 109.5 . . ?
C25 C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C25 C26B H26D 109.5 . . ?
C25 C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25 C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
O24B C27 C28 106.0(4) . . ?
O24B C27 H27A 110.5 . . ?
C28 C27 H27A 110.5 . . ?
O24B C27 H27B 110.5 . . ?
C28 C27 H27B 110.5 . . ?
H27A C27 H27B 108.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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-deox2-tbpy2--h2o
_database_code_depnum_ccdc_archive 'CCDC 1549268'
_audit_update_record             
;
2017-05-11 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
 
;
_chemical_formula_moiety         'C34 H48 Co N2 O10, H2 O'
_chemical_formula_sum            'C34 H50 Co N2 O11'
_chemical_formula_weight         721.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   11.6167(6)
_cell_length_b                   11.6167(6)
_cell_length_c                   27.9840(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3776.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4573
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      19.52

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             1532
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.511
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            29341
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.455
_diffrn_reflns_theta_max         28.821
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4726
_reflns_number_gt                3204
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    1.000

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SHELXTL-NT 6.1 (Bruker)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.2247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4726
_refine_ls_number_parameters     245
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.000000 0.500000 0.89105(2) 0.04253(16) Uani 1 2 d S T P . .
N1 N -0.0800(2) 0.3299(2) 0.89073(10) 0.0469(6) Uani 1 1 d . . . . .
C2 C -0.0856(3) 0.2646(3) 0.92929(13) 0.0552(10) Uani 1 1 d . . . . .
H2 H -0.057290 0.293988 0.957874 0.066 Uiso 1 1 calc R U . . .
C3 C -0.1315(3) 0.1546(3) 0.92938(13) 0.0563(10) Uani 1 1 d . . . . .
H3 H -0.133283 0.112539 0.957660 0.068 Uiso 1 1 calc R U . . .
C4 C -0.1745(3) 0.1067(3) 0.88806(12) 0.0470(8) Uani 1 1 d . . . . .
C5 C -0.1691(3) 0.1763(3) 0.84812(12) 0.0510(9) Uani 1 1 d . . . . .
H5 H -0.197682 0.149581 0.819117 0.061 Uiso 1 1 calc R U . . .
C6 C -0.1220(3) 0.2847(3) 0.85083(12) 0.0525(9) Uani 1 1 d . . . . .
H6 H -0.119420 0.328861 0.823128 0.063 Uiso 1 1 calc R U . . .
C7 C -0.2237(3) -0.0157(3) 0.88525(13) 0.0542(9) Uani 1 1 d . . . . .
C8 C -0.3488(4) -0.0093(5) 0.8704(2) 0.0975(15) Uani 1 1 d . . . . .
H8A H -0.353820 0.019760 0.838310 0.146 Uiso 1 1 calc R U . . .
H8B H -0.389533 0.041186 0.891596 0.146 Uiso 1 1 calc R U . . .
H8C H -0.382273 -0.084770 0.871715 0.146 Uiso 1 1 calc R U . . .
C9 C -0.2150(5) -0.0799(4) 0.93276(18) 0.1031(18) Uani 1 1 d . . . . .
H9A H -0.243050 -0.157079 0.928822 0.155 Uiso 1 1 calc R U . . .
H9B H -0.260424 -0.040922 0.956411 0.155 Uiso 1 1 calc R U . . .
H9C H -0.136097 -0.082107 0.942909 0.155 Uiso 1 1 calc R U . . .
C10 C -0.1551(4) -0.0835(4) 0.84756(17) 0.0832(14) Uani 1 1 d . . . . .
H10A H -0.171903 -0.053578 0.816347 0.125 Uiso 1 1 calc R U . . .
H10B H -0.176371 -0.163270 0.848925 0.125 Uiso 1 1 calc R U . . .
H10C H -0.074237 -0.075877 0.853881 0.125 Uiso 1 1 calc R U . . .
C18 C -0.3258(4) 0.5865(4) 1.05989(15) 0.0749(13) Uani 1 1 d . . . . .
H18A H -0.393467 0.542278 1.052824 0.112 Uiso 1 1 calc R U . . .
H18B H -0.344474 0.666991 1.059491 0.112 Uiso 1 1 calc R U . . .
H18C H -0.297343 0.565712 1.090922 0.112 Uiso 1 1 calc R U . . .
C17 C -0.2358(3) 0.5625(4) 1.02333(12) 0.0655(11) Uani 1 1 d . . . . .
H17A H -0.167557 0.607981 1.029813 0.079 Uiso 1 1 calc R U . . .
H17B H -0.214723 0.481746 1.024093 0.079 Uiso 1 1 calc R U . . .
O5 O -0.2822(2) 0.5920(2) 0.97700(8) 0.0569(7) Uani 1 1 d . . . . .
C16 C -0.2132(3) 0.5766(3) 0.93946(12) 0.0437(8) Uani 1 1 d . . . . .
O4 O -0.1129(2) 0.5472(2) 0.94556(7) 0.0486(6) Uani 1 1 d . . . . .
C15 C -0.2693(3) 0.5976(3) 0.89491(12) 0.0517(8) Uani 1 1 d . . . . .
H15 H -0.345948 0.620641 0.895694 0.062 Uiso 1 1 calc R U . . .
C14 C -0.2183(3) 0.5864(3) 0.85137(11) 0.0446(8) Uani 1 1 d . . . . .
O1 O -0.1157(2) 0.5553(2) 0.84195(8) 0.0519(6) Uani 1 1 d . . . . .
C13 C -0.2877(3) 0.6135(3) 0.80664(13) 0.0557(9) Uani 1 1 d D . . . .
O2 O -0.2539(3) 0.6000(3) 0.76734(10) 0.0863(10) Uani 1 1 d . . . . .
O3 O -0.3921(2) 0.6540(3) 0.81635(10) 0.0868(10) Uani 1 1 d D . . . .
C12A C -0.4632(7) 0.6772(16) 0.7743(2) 0.082(4) Uani 0.74(2) 1 d D . P A 1
H12A H -0.463023 0.611861 0.752725 0.099 Uiso 0.74(2) 1 calc R U P A 1
H12B H -0.435500 0.744448 0.757288 0.099 Uiso 0.74(2) 1 calc R U P A 1
C11A C -0.5819(6) 0.6979(13) 0.7940(4) 0.094(4) Uani 0.74(2) 1 d D . P A 1
H11A H -0.634077 0.713873 0.768259 0.141 Uiso 0.74(2) 1 calc R U P A 1
H11B H -0.607419 0.630672 0.810955 0.141 Uiso 0.74(2) 1 calc R U P A 1
H11C H -0.580080 0.762372 0.815487 0.141 Uiso 0.74(2) 1 calc R U P A 1
C12B C -0.457(2) 0.733(3) 0.7863(14) 0.103(13) Uani 0.26(2) 1 d D . P A 2
H12C H -0.415369 0.751531 0.757352 0.124 Uiso 0.26(2) 1 calc R U P A 2
H12D H -0.475443 0.803350 0.803234 0.124 Uiso 0.26(2) 1 calc R U P A 2
C11B C -0.565(3) 0.665(3) 0.7752(16) 0.16(2) Uani 0.26(2) 1 d D . P A 2
H11D H -0.614774 0.710273 0.755152 0.247 Uiso 0.26(2) 1 calc R U P A 2
H11E H -0.544730 0.595270 0.758858 0.247 Uiso 0.26(2) 1 calc R U P A 2
H11F H -0.604316 0.646668 0.804369 0.247 Uiso 0.26(2) 1 calc R U P A 2
O10 O 0.000000 0.500000 0.74846(17) 0.137(3) Uani 1 2 d S T P . .
H10 H -0.061(5) 0.505(9) 0.765(2) 0.164 Uiso 1 1 d . 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 O1 2.026(2) . ?
Co1 O1 2.026(2) 2_565 ?
Co1 O4 2.085(2) . ?
Co1 O4 2.086(2) 2_565 ?
Co1 N1 2.183(3) . ?
Co1 N1 2.183(3) 2_565 ?
N1 C2 1.321(4) . ?
N1 C6 1.327(4) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(5) . ?
C4 C7 1.535(5) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.513(5) . ?
C7 C9 1.528(6) . ?
C7 C10 1.538(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C18 C17 1.489(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 O5 1.445(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O5 C16 1.333(4) . ?
C16 O4 1.225(4) . ?
C16 C15 1.428(5) . ?
C15 C14 1.361(5) . ?
C15 H15 0.9300 . ?
C14 O1 1.273(4) . ?
C14 C13 1.522(5) . ?
C13 O2 1.178(4) . ?
C13 O3 1.328(3) . ?
O3 C12B 1.456(4) . ?
O3 C12A 1.463(4) . ?
C12A C11A 1.505(4) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12B C11B 1.511(4) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
O10 H10 0.84(6) . ?
O10 H10 0.84(6) 2_565 ?

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 O1 94.61(13) . 2_565 ?
O1 Co1 O4 89.74(9) . . ?
O1 Co1 O4 175.23(9) 2_565 . ?
O1 Co1 O4 175.23(9) . 2_565 ?
O1 Co1 O4 89.74(9) 2_565 2_565 ?
O4 Co1 O4 85.97(12) . 2_565 ?
O1 Co1 N1 90.11(10) . . ?
O1 Co1 N1 89.58(10) 2_565 . ?
O4 Co1 N1 88.47(10) . . ?
O4 Co1 N1 91.87(10) 2_565 . ?
O1 Co1 N1 89.58(10) . 2_565 ?
O1 Co1 N1 90.11(10) 2_565 2_565 ?
O4 Co1 N1 91.87(10) . 2_565 ?
O4 Co1 N1 88.47(10) 2_565 2_565 ?
N1 Co1 N1 179.53(15) . 2_565 ?
C2 N1 C6 116.2(3) . . ?
C2 N1 Co1 122.5(2) . . ?
C6 N1 Co1 121.2(2) . . ?
N1 C2 C3 123.4(3) . . ?
N1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 115.3(3) . . ?
C3 C4 C7 123.5(3) . . ?
C5 C4 C7 121.2(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
N1 C6 C5 123.7(3) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C8 C7 C9 109.1(4) . . ?
C8 C7 C4 109.0(3) . . ?
C9 C7 C4 112.5(3) . . ?
C8 C7 C10 109.5(4) . . ?
C9 C7 C10 108.2(4) . . ?
C4 C7 C10 108.4(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C17 C18 108.1(3) . . ?
O5 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O5 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C16 O5 C17 116.8(3) . . ?
O4 C16 O5 119.9(3) . . ?
O4 C16 C15 127.1(3) . . ?
O5 C16 C15 113.0(3) . . ?
C16 O4 Co1 124.7(2) . . ?
C14 C15 C16 124.5(3) . . ?
C14 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
O1 C14 C15 128.3(3) . . ?
O1 C14 C13 112.6(3) . . ?
C15 C14 C13 119.0(3) . . ?
C14 O1 Co1 124.8(2) . . ?
O2 C13 O3 122.8(3) . . ?
O2 C13 C14 124.3(3) . . ?
O3 C13 C14 112.9(3) . . ?
C13 O3 C12B 125.4(17) . . ?
C13 O3 C12A 114.6(4) . . ?
O3 C12A C11A 104.6(5) . . ?
O3 C12A H12A 110.8 . . ?
C11A C12A H12A 110.8 . . ?
O3 C12A H12B 110.8 . . ?
C11A C12A H12B 110.8 . . ?
H12A C12A H12B 108.9 . . ?
C12A C11A H11A 109.5 . . ?
C12A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C12A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
O3 C12B C11B 102.9(14) . . ?
O3 C12B H12C 111.2 . . ?
C11B C12B H12C 111.2 . . ?
O3 C12B H12D 111.2 . . ?
C11B C12B H12D 111.2 . . ?
H12C C12B H12D 109.1 . . ?
C12B C11B H11D 109.5 . . ?
C12B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C12B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
H10 O10 H10 114(9) . 2_565 ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
