# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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 
# this file and to allow appropriate attribution of the data. 
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data_1_Mg_eda
_database_code_depnum_ccdc_archive 'CCDC 1551123'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Mg2 N2 O13'
_chemical_formula_weight         398.86

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'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   13.9212(2)
_cell_length_b                   13.9212(2)
_cell_length_c                   22.6133(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3795.31(14)
_cell_formula_units_Z            9
_cell_measurement_temperature    295
_cell_measurement_reflns_used    8611
_cell_measurement_theta_min      2.926
_cell_measurement_theta_max      25.998

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean 10.4508
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8611
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.926
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.861
_reflns_number_total             2852
_reflns_number_gt                2777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.720
_reflns_Friedel_fraction_full    0.728

_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+(0.0438P)²+4.2359P] 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 
;
 Flack x determined using 1125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2852
_refine_ls_number_parameters     234
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.139
_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
Mg0 Mg 0.66901(8) 0.66023(7) 0.69600(6) 0.0118(2) Uani 1 1 d . . . . .
C1 C 0.6417(3) 0.4910(3) 0.60264(15) 0.0216(7) Uani 1 1 d . . . . .
H1 H 0.7097 0.5463 0.5884 0.026 Uiso 1 1 calc R U . . .
Mg1 Mg 0.6667 0.3333 0.52106(8) 0.0123(4) Uani 1 3 d S T P . .
O1 O 0.60367(19) 0.51317(18) 0.64689(11) 0.0252(5) Uani 1 1 d . . . . .
Mg2 Mg 1.0000 1.0000 0.53702(8) 0.0127(4) Uani 1 3 d S T P . .
O2 O 0.59644(19) 0.40111(19) 0.57576(12) 0.0239(5) Uani 1 1 d . . . . .
C2 C 0.8566(3) 0.8159(3) 0.61951(16) 0.0229(7) Uani 1 1 d . . . . .
H2 H 0.8197 0.8559 0.6222 0.027 Uiso 1 1 calc R U . . .
C3 C 0.8220(3) 0.8509(3) 0.77474(16) 0.0222(7) Uani 1 1 d . . . . .
H3 H 0.8667 0.8191 0.7708 0.027 Uiso 1 1 calc R U . . .
Mg3 Mg 1.0000 1.0000 0.85914(9) 0.0120(3) Uani 1 3 d S T P . .
O3 O 0.81551(17) 0.72628(18) 0.64792(10) 0.0196(5) Uani 1 1 d . . . . .
C4 C 0.4862(3) 0.6287(3) 0.77736(19) 0.0297(8) Uani 1 1 d . . . . .
H4 H 0.5343 0.7031 0.7859 0.036 Uiso 1 1 calc R U . . .
O4 O 0.94081(18) 0.85615(18) 0.58845(11) 0.0233(5) Uani 1 1 d . . . . .
O9 O 0.52101(18) 0.58456(19) 0.74263(11) 0.0236(5) Uani 1 1 d . . . . .
O8 O 0.85662(18) 0.93351(18) 0.80726(12) 0.0235(5) Uani 1 1 d . . . . .
O7 O 0.73192(18) 0.80642(18) 0.74663(11) 0.0215(5) Uani 1 1 d . . . . .
O10 O 0.39448(18) 0.58522(19) 0.80221(12) 0.0241(6) Uani 1 1 d . . . . .
O5 O 0.60258(19) 0.7253(2) 0.63578(12) 0.0256(5) Uani 1 1 d . . . . .
C5 C 0.6942(3) 0.5109(3) 0.78269(16) 0.0239(7) Uani 1 1 d . . . . .
H5 H 0.6186 0.4658 0.7759 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5092(3) 0.6850(3) 0.61471(16) 0.0227(7) Uani 1 1 d . . . . .
H6 H 0.4569 0.6147 0.6279 0.027 Uiso 1 1 calc R U . . .
O6 O 0.47730(18) 0.72901(19) 0.57716(11) 0.0230(5) Uani 1 1 d . . . . .
O12 O 0.73658(18) 0.47731(18) 0.82021(12) 0.0236(5) Uani 1 1 d . . . . .
O11 O 0.7419(2) 0.59742(19) 0.75363(11) 0.0251(6) Uani 1 1 d . . . . .
N21 N 0.3955(2) 0.3267(2) 0.67582(16) 0.0316(7) Uani 1 1 d . . . . .
H21A H 0.3841 0.2581 0.6725 0.047 Uiso 1 1 calc R U . . .
H21B H 0.3841 0.3390 0.7131 0.047 Uiso 1 1 calc R U . . .
H21C H 0.4650 0.3751 0.6655 0.047 Uiso 1 1 calc R U . . .
C21 C 0.3175(3) 0.3399(3) 0.6364(2) 0.0313(9) Uani 1 1 d . . . . .
H21D H 0.3208 0.4097 0.6450 0.038 Uiso 1 1 calc R U . . .
H21E H 0.2425 0.2805 0.6439 0.038 Uiso 1 1 calc R U . . .
N22 N 0.2622(2) 0.3392(2) 0.53311(16) 0.0311(7) Uani 1 1 d . . . . .
H22A H 0.2876 0.3529 0.4962 0.047 Uiso 1 1 calc R U . . .
H22B H 0.2482 0.3920 0.5450 0.047 Uiso 1 1 calc R U . . .
H22C H 0.2002 0.2737 0.5346 0.047 Uiso 1 1 calc R U . . .
C22 C 0.3460(3) 0.3378(3) 0.5720(2) 0.0350(10) Uani 1 1 d . . . . .
H22D H 0.4180 0.4017 0.5636 0.042 Uiso 1 1 calc R U . . .
H22E H 0.3503 0.2715 0.5643 0.042 Uiso 1 1 calc R U . . .
OW O 0.3980(2) 0.3691(2) 0.43828(14) 0.0324(6) Uani 1 1 d D . . . .
HW1 H 0.440(4) 0.434(4) 0.428(2) 0.039 Uiso 1 1 d D U . . .
HW2 H 0.443(4) 0.337(4) 0.445(2) 0.039 Uiso 1 1 d 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
Mg0 O9 2.073(2) . ?
Mg0 O3 2.076(2) . ?
Mg0 O5 2.090(2) . ?
Mg0 O11 2.093(2) . ?
Mg0 O1 2.095(2) . ?
Mg0 O7 2.107(2) . ?
C1 O1 1.241(4) . ?
C1 O2 1.243(4) . ?
C1 H1 0.9300 . ?
Mg1 O2 2.073(2) 3_665 ?
Mg1 O2 2.073(2) 2_655 ?
Mg1 O2 2.073(2) . ?
Mg1 O10 2.090(2) 8_654 ?
Mg1 O10 2.090(2) 9_554 ?
Mg1 O10 2.090(2) 7_544 ?
Mg2 O12 2.073(2) 7_554 ?
Mg2 O12 2.073(2) 8_654 ?
Mg2 O12 2.074(2) 9_664 ?
Mg2 O4 2.096(2) 2_765 ?
Mg2 O4 2.096(2) . ?
Mg2 O4 2.096(2) 3_675 ?
C2 O4 1.235(4) . ?
C2 O3 1.258(4) . ?
C2 H2 0.9300 . ?
C3 O8 1.242(4) . ?
C3 O7 1.259(4) . ?
C3 H3 0.9300 . ?
Mg3 O8 2.090(2) . ?
Mg3 O8 2.090(2) 2_765 ?
Mg3 O8 2.090(2) 3_675 ?
Mg3 O6 2.093(2) 4 ?
Mg3 O6 2.093(2) 6_565 ?
Mg3 O6 2.093(2) 5_665 ?
C4 O9 1.236(4) . ?
C4 O10 1.241(4) . ?
C4 H4 0.9300 . ?
O10 Mg1 2.090(2) 4_455 ?
O5 C6 1.225(4) . ?
C5 O11 1.235(4) . ?
C5 O12 1.249(4) . ?
C5 H5 0.9300 . ?
C6 O6 1.252(4) . ?
C6 H6 0.9300 . ?
O6 Mg3 2.093(2) 7_444 ?
O12 Mg2 2.073(2) 4_445 ?
N21 C21 1.486(5) . ?
N21 H21A 0.8900 . ?
N21 H21B 0.8900 . ?
N21 H21C 0.8900 . ?
C21 C22 1.512(6) . ?
C21 H21D 0.9700 . ?
C21 H21E 0.9700 . ?
N22 C22 1.469(5) . ?
N22 H22A 0.8900 . ?
N22 H22B 0.8900 . ?
N22 H22C 0.8900 . ?
C22 H22D 0.9700 . ?
C22 H22E 0.9700 . ?
OW HW1 0.83(5) . ?
OW HW2 0.94(4) . ?

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
O9 Mg0 O3 176.44(10) . . ?
O9 Mg0 O5 90.51(11) . . ?
O3 Mg0 O5 90.94(10) . . ?
O9 Mg0 O11 92.14(10) . . ?
O3 Mg0 O11 86.38(10) . . ?
O5 Mg0 O11 177.30(12) . . ?
O9 Mg0 O1 86.42(10) . . ?
O3 Mg0 O1 90.32(10) . . ?
O5 Mg0 O1 90.46(11) . . ?
O11 Mg0 O1 89.21(10) . . ?
O9 Mg0 O7 92.40(10) . . ?
O3 Mg0 O7 90.85(10) . . ?
O5 Mg0 O7 89.76(10) . . ?
O11 Mg0 O7 90.63(10) . . ?
O1 Mg0 O7 178.80(11) . . ?
O1 C1 O2 125.5(3) . . ?
O1 C1 H1 117.2 . . ?
O2 C1 H1 117.2 . . ?
O2 Mg1 O2 88.05(12) 3_665 2_655 ?
O2 Mg1 O2 88.05(12) 3_665 . ?
O2 Mg1 O2 88.05(12) 2_655 . ?
O2 Mg1 O10 87.37(9) 3_665 8_654 ?
O2 Mg1 O10 175.14(10) 2_655 8_654 ?
O2 Mg1 O10 93.44(10) . 8_654 ?
O2 Mg1 O10 175.14(10) 3_665 9_554 ?
O2 Mg1 O10 93.44(10) 2_655 9_554 ?
O2 Mg1 O10 87.38(9) . 9_554 ?
O10 Mg1 O10 91.26(12) 8_654 9_554 ?
O2 Mg1 O10 93.44(10) 3_665 7_544 ?
O2 Mg1 O10 87.37(9) 2_655 7_544 ?
O2 Mg1 O10 175.14(10) . 7_544 ?
O10 Mg1 O10 91.25(12) 8_654 7_544 ?
O10 Mg1 O10 91.26(12) 9_554 7_544 ?
C1 O1 Mg0 129.8(2) . . ?
O12 Mg2 O12 92.95(11) 7_554 8_654 ?
O12 Mg2 O12 92.95(11) 7_554 9_664 ?
O12 Mg2 O12 92.95(11) 8_654 9_664 ?
O12 Mg2 O4 84.55(9) 7_554 2_765 ?
O12 Mg2 O4 175.89(9) 8_654 2_765 ?
O12 Mg2 O4 90.45(10) 9_664 2_765 ?
O12 Mg2 O4 175.88(9) 7_554 . ?
O12 Mg2 O4 90.45(10) 8_654 . ?
O12 Mg2 O4 84.55(9) 9_664 . ?
O4 Mg2 O4 92.18(11) 2_765 . ?
O12 Mg2 O4 90.46(10) 7_554 3_675 ?
O12 Mg2 O4 84.56(9) 8_654 3_675 ?
O12 Mg2 O4 175.88(9) 9_664 3_675 ?
O4 Mg2 O4 92.18(11) 2_765 3_675 ?
O4 Mg2 O4 92.18(11) . 3_675 ?
C1 O2 Mg1 129.3(2) . . ?
O4 C2 O3 126.7(3) . . ?
O4 C2 H2 116.6 . . ?
O3 C2 H2 116.6 . . ?
O8 C3 O7 125.7(3) . . ?
O8 C3 H3 117.1 . . ?
O7 C3 H3 117.1 . . ?
O8 Mg3 O8 91.58(11) . 2_765 ?
O8 Mg3 O8 91.58(11) . 3_675 ?
O8 Mg3 O8 91.58(11) 2_765 3_675 ?
O8 Mg3 O6 178.27(10) . 4 ?
O8 Mg3 O6 86.93(9) 2_765 4 ?
O8 Mg3 O6 89.34(9) 3_675 4 ?
O8 Mg3 O6 86.92(9) . 6_565 ?
O8 Mg3 O6 89.34(9) 2_765 6_565 ?
O8 Mg3 O6 178.27(10) 3_675 6_565 ?
O6 Mg3 O6 92.18(11) 4 6_565 ?
O8 Mg3 O6 89.34(9) . 5_665 ?
O8 Mg3 O6 178.27(10) 2_765 5_665 ?
O8 Mg3 O6 86.93(9) 3_675 5_665 ?
O6 Mg3 O6 92.18(11) 4 5_665 ?
O6 Mg3 O6 92.18(11) 6_565 5_665 ?
C2 O3 Mg0 124.4(2) . . ?
O9 C4 O10 127.5(3) . . ?
O9 C4 H4 116.3 . . ?
O10 C4 H4 116.3 . . ?
C2 O4 Mg2 125.4(2) . . ?
C4 O9 Mg0 127.4(2) . . ?
C3 O8 Mg3 125.8(2) . . ?
C3 O7 Mg0 125.5(2) . . ?
C4 O10 Mg1 126.1(2) . 4_455 ?
C6 O5 Mg0 130.7(2) . . ?
O11 C5 O12 127.0(3) . . ?
O11 C5 H5 116.5 . . ?
O12 C5 H5 116.5 . . ?
O5 C6 O6 126.5(3) . . ?
O5 C6 H6 116.8 . . ?
O6 C6 H6 116.8 . . ?
C6 O6 Mg3 132.4(2) . 7_444 ?
C5 O12 Mg2 130.7(2) . 4_445 ?
C5 O11 Mg0 127.1(2) . . ?
C21 N21 H21A 109.5 . . ?
C21 N21 H21B 109.5 . . ?
H21A N21 H21B 109.5 . . ?
C21 N21 H21C 109.5 . . ?
H21A N21 H21C 109.5 . . ?
H21B N21 H21C 109.5 . . ?
N21 C21 C22 111.2(3) . . ?
N21 C21 H21D 109.4 . . ?
C22 C21 H21D 109.4 . . ?
N21 C21 H21E 109.4 . . ?
C22 C21 H21E 109.4 . . ?
H21D C21 H21E 108.0 . . ?
C22 N22 H22A 109.5 . . ?
C22 N22 H22B 109.5 . . ?
H22A N22 H22B 109.5 . . ?
C22 N22 H22C 109.5 . . ?
H22A N22 H22C 109.5 . . ?
H22B N22 H22C 109.5 . . ?
N22 C22 C21 111.1(3) . . ?
N22 C22 H22D 109.4 . . ?
C21 C22 H22D 109.4 . . ?
N22 C22 H22E 109.4 . . ?
C21 C22 H22E 109.4 . . ?
H22D C22 H22E 108.0 . . ?
HW1 OW HW2 107(4) . . ?

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
O2 C1 O1 Mg0 -179.3(3) . . . . ?
O1 C1 O2 Mg1 -157.8(3) . . . . ?
O4 C2 O3 Mg0 -176.9(3) . . . . ?
O3 C2 O4 Mg2 175.4(3) . . . . ?
O10 C4 O9 Mg0 174.7(3) . . . . ?
O7 C3 O8 Mg3 174.9(3) . . . . ?
O8 C3 O7 Mg0 -175.8(3) . . . . ?
O9 C4 O10 Mg1 -173.8(3) . . . 4_455 ?
Mg0 O5 C6 O6 -177.6(3) . . . . ?
O5 C6 O6 Mg3 168.2(3) . . . 7_444 ?
O11 C5 O12 Mg2 -178.7(3) . . . 4_445 ?
O12 C5 O11 Mg0 -174.5(3) . . . . ?
N21 C21 C22 N22 174.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O3 0.93 2.56 3.116(4) 118.5 .
C2 H2 O4 0.93 2.57 3.141(4) 120.3 3_675
C2 H2 O5 0.93 2.65 3.126(4) 112.2 .
C3 H3 O8 0.93 2.55 3.116(4) 119.8 2_765
C4 H4 O7 0.93 2.54 3.137(4) 122.1 .
N21 H21A O3 0.89 2.14 2.932(4) 147.7 2_655
N21 H21A O11 0.89 2.52 3.129(4) 126.4 2_655
N21 H21B OW 0.89 1.92 2.733(4) 150.6 5
N21 H21C O1 0.89 1.97 2.836(4) 163.3 .
N21 H21C O2 0.89 2.63 3.335(4) 136.3 .
C21 H21E O4 0.97 2.67 3.325(4) 124.9 2_655
N22 H22A OW 0.89 1.94 2.749(4) 149.6 .
N22 H22B O6 0.89 1.94 2.813(4) 167.1 3_565
N22 H22C O12 0.89 2.11 2.893(4) 146.9 7_444
C22 H22D O2 0.97 2.50 3.142(4) 123.2 .
OW HW1 O8 0.83(5) 2.70(5) 3.163(3) 117(4) 8_654
OW HW1 O7 0.83(5) 1.94(5) 2.758(4) 171(5) 8_654
OW HW2 O9 0.94(4) 2.54(4) 3.172(4) 125(3) 9_554
OW HW2 O10 0.94(4) 1.85(5) 2.784(4) 172(4) 9_554

_refine_diff_density_max         0.458
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_4_Ni_eda
_database_code_depnum_ccdc_archive 'CCDC 1537667'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N2 Ni2 O13'
_chemical_formula_weight         467.66

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           182
_space_group_name_H-M_alt        'P 63 2 2'
_space_group_name_Hall           'P 6c 2c'

_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'
'-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                   8.0241(4)
_cell_length_b                   8.0241(4)
_cell_length_c                   7.3421(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     409.40(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    295
_cell_measurement_reflns_used    2838
_cell_measurement_theta_min      4.038
_cell_measurement_theta_max      26.957

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    2.371
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean 10.4508
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2838
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.038
_diffrn_reflns_theta_max         26.957
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             301
_reflns_number_gt                288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.440
_reflns_Friedel_fraction_max     1.000
_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+(0.0191P)²+0.1039P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 85 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.10(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         301
_refine_ls_number_parameters     46
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0455
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.159
_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
Ni0 Ni 0.6667 0.3333 0.2500 0.0194(2) Uani 1 6 d S T P . .
O1 O 0.4490(3) 0.3238(3) 0.4074(2) 0.0335(5) Uani 1 1 d . . . . .
C1 C 0.4554(5) 0.4554(5) 0.5000 0.0314(10) Uani 1 2 d S T P . .
N21 N 0.079(5) -0.066(5) 0.289(2) 0.044(4) Uani 0.1667 1 d . U P . .
H1 H 0.582(7) 0.582(7) 0.5000 0.08(2) Uiso 1 2 d S . P . .
H21A H 0.0397 -0.0320 0.3925 0.123 Uiso 0.1667 1 d R U P . .
H21B H 0.0341 -0.1921 0.2900 0.123 Uiso 0.1667 1 d R U P . .
H21C H 0.2098 -0.0023 0.2900 0.123 Uiso 0.1667 1 d R U P . .
C21 C 0.0000 0.0000 0.1016(19) 0.065(3) Uani 0.5 3 d DS TU P . .
H21D H 0.032(13) 0.129(4) 0.138(16) 0.079 Uiso 0.1667 1 d D U P . .
H21E H -0.128(5) -0.044(11) 0.150(12) 0.079 Uiso 0.1667 1 d D U P . .
OW O 0.0000 0.101(3) 0.5000 0.045(5) Uani 0.1667 2 d DS TU P . .
HW1 H 0.0000 0.0000 0.530(12) 0.054 Uiso 0.25 3 d DS U P . .
HW2 H -0.07(4) 0.12(3) 0.58(3) 0.054 Uiso 0.0833 1 d D U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni0 O1 2.0633(19) 11_655 ?
Ni0 O1 2.0633(19) 2_655 ?
Ni0 O1 2.0633(19) 3_665 ?
Ni0 O1 2.0633(19) 12 ?
Ni0 O1 2.0633(19) 10_665 ?
Ni0 O1 2.0633(19) . ?
O1 C1 1.235(3) . ?
C1 O1 1.235(3) 7_556 ?
C1 H1 1.02(6) . ?
N21 N21 0.57(3) 10 ?
N21 C21 1.294(16) 10 ?
N21 OW 1.622(17) 3 ?
N21 C21 1.705(19) . ?
N21 N21 1.75(2) 3 ?
N21 N21 1.75(2) 2 ?
N21 N21 1.79(4) 12 ?
N21 N21 1.89(4) 11 ?
N21 H21A 0.9194 . ?
N21 H21B 0.8858 . ?
N21 H21C 0.9084 . ?
C21 OW 1.102(16) 6_554 ?
C21 OW 1.102(16) 4_554 ?
C21 OW 1.102(16) 5_554 ?
C21 N21 1.294(16) 11 ?
C21 N21 1.294(16) 12 ?
C21 N21 1.294(16) 10 ?
C21 C21 1.49(3) 7 ?
C21 N21 1.705(19) 2 ?
C21 N21 1.705(19) 3 ?
C21 H21D 0.9700(14) . ?
C21 H21E 0.9700(14) . ?
OW C21 1.102(16) 10 ?
OW C21 1.102(16) 4 ?
OW OW 1.40(4) 2 ?
OW OW 1.40(4) 3 ?
OW N21 1.622(17) 7_556 ?
OW N21 1.622(18) 2 ?
OW HW1 0.841(14) . ?
OW HW2 0.841(14) . ?

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 Ni0 O1 85.73(11) 11_655 2_655 ?
O1 Ni0 O1 90.99(12) 11_655 3_665 ?
O1 Ni0 O1 91.70(8) 2_655 3_665 ?
O1 Ni0 O1 91.70(8) 11_655 12 ?
O1 Ni0 O1 90.99(12) 2_655 12 ?
O1 Ni0 O1 176.33(12) 3_665 12 ?
O1 Ni0 O1 91.70(8) 11_655 10_665 ?
O1 Ni0 O1 176.33(12) 2_655 10_665 ?
O1 Ni0 O1 85.73(11) 3_665 10_665 ?
O1 Ni0 O1 91.70(8) 12 10_665 ?
O1 Ni0 O1 176.33(12) 11_655 . ?
O1 Ni0 O1 91.70(8) 2_655 . ?
O1 Ni0 O1 91.70(8) 3_665 . ?
O1 Ni0 O1 85.73(11) 12 . ?
O1 Ni0 O1 90.99(12) 10_665 . ?
C1 O1 Ni0 127.2(2) . . ?
O1 C1 O1 126.8(4) . 7_556 ?
O1 C1 H1 116.6(2) . . ?
O1 C1 H1 116.6(2) 7_556 . ?
N21 N21 C21 127(2) 10 10 ?
N21 N21 OW 169(2) 10 3 ?
C21 N21 OW 42.6(9) 10 3 ?
N21 N21 C21 37.1(13) 10 . ?
C21 N21 C21 92.1(11) 10 . ?
OW N21 C21 131.6(12) 3 . ?
N21 N21 N21 84(5) 10 3 ?
C21 N21 N21 47.4(6) 10 3 ?
OW N21 N21 87.6(9) 3 3 ?
C21 N21 N21 59.1(4) . 3 ?
N21 N21 N21 95(3) 10 2 ?
C21 N21 N21 47.4(6) 10 2 ?
OW N21 N21 74.4(10) 3 2 ?
C21 N21 N21 59.1(4) . 2 ?
N21 N21 N21 60.001(2) 3 2 ?
N21 N21 N21 77(4) 10 12 ?
C21 N21 N21 64.8(15) 10 12 ?
OW N21 N21 92.4(15) 3 12 ?
C21 N21 N21 43.4(9) . 12 ?
N21 N21 N21 64(2) 3 12 ?
N21 N21 N21 18.6(12) 2 12 ?
N21 N21 N21 68(3) 10 11 ?
C21 N21 N21 61.5(15) 10 11 ?
OW N21 N21 103.5(16) 3 11 ?
C21 N21 N21 41.8(9) . 11 ?
N21 N21 N21 17.7(9) 3 11 ?
N21 N21 N21 59(2) 2 11 ?
N21 N21 N21 56.8(3) 12 11 ?
N21 N21 H21A 144.4 10 . ?
C21 N21 H21A 17.6 10 . ?
OW N21 H21A 26.4 3 . ?
C21 N21 H21A 109.7 . . ?
N21 N21 H21A 61.3 3 . ?
N21 N21 H21A 60.9 2 . ?
N21 N21 H21A 79.3 12 . ?
N21 N21 H21A 77.1 11 . ?
N21 N21 H21B 82.8 10 . ?
C21 N21 H21B 117.2 10 . ?
OW N21 H21B 106.1 3 . ?
C21 N21 H21B 111.3 . . ?
N21 N21 H21B 96.4 3 . ?
N21 N21 H21B 156.4 2 . ?
N21 N21 H21B 153.1 12 . ?
N21 N21 H21B 99.1 11 . ?
H21A N21 H21B 109.0 . . ?
N21 N21 H21C 99.5 10 . ?
C21 N21 H21C 115.1 10 . ?
OW N21 H21C 84.1 3 . ?
C21 N21 H21C 109.8 . . ?
N21 N21 H21C 153.6 3 . ?
N21 N21 H21C 93.6 2 . ?
N21 N21 H21C 90.9 12 . ?
N21 N21 H21C 146.7 11 . ?
H21A N21 H21C 107.0 . . ?
H21B N21 H21C 110.0 . . ?
OW C21 OW 79.2(15) 6_554 4_554 ?
OW C21 OW 79.2(15) 6_554 5_554 ?
OW C21 OW 79.2(15) 4_554 5_554 ?
OW C21 N21 84.8(11) 6_554 11 ?
OW C21 N21 116.8(15) 4_554 11 ?
OW C21 N21 154.8(17) 5_554 11 ?
OW C21 N21 116.8(15) 6_554 12 ?
OW C21 N21 154.8(17) 4_554 12 ?
OW C21 N21 84.8(11) 5_554 12 ?
N21 C21 N21 85.3(12) 11 12 ?
OW C21 N21 154.8(17) 6_554 10 ?
OW C21 N21 84.8(11) 4_554 10 ?
OW C21 N21 116.8(15) 5_554 10 ?
N21 C21 N21 85.3(12) 11 10 ?
N21 C21 N21 85.3(12) 12 10 ?
OW C21 C21 47.4(10) 6_554 7 ?
OW C21 C21 47.4(10) 4_554 7 ?
OW C21 C21 47.4(10) 5_554 7 ?
N21 C21 C21 128.6(8) 11 7 ?
N21 C21 C21 128.6(8) 12 7 ?
N21 C21 C21 128.6(8) 10 7 ?
OW C21 N21 121.5(13) 6_554 2 ?
OW C21 N21 159.0(15) 4_554 2 ?
OW C21 N21 100.3(10) 5_554 2 ?
N21 C21 N21 72(2) 11 2 ?
N21 C21 N21 15.5(12) 12 2 ?
N21 C21 N21 77(2) 10 2 ?
C21 C21 N21 143.6(5) 7 2 ?
OW C21 N21 159.0(15) 6_554 . ?
OW C21 N21 100.3(10) 4_554 . ?
OW C21 N21 121.5(13) 5_554 . ?
N21 C21 N21 77(2) 11 . ?
N21 C21 N21 72(2) 12 . ?
N21 C21 N21 15.5(12) 10 . ?
C21 C21 N21 143.6(5) 7 . ?
N21 C21 N21 61.9(9) 2 . ?
OW C21 N21 100.3(10) 6_554 3 ?
OW C21 N21 121.5(13) 4_554 3 ?
OW C21 N21 159.0(15) 5_554 3 ?
N21 C21 N21 15.5(12) 11 3 ?
N21 C21 N21 77(2) 12 3 ?
N21 C21 N21 72(2) 10 3 ?
C21 C21 N21 143.6(5) 7 3 ?
N21 C21 N21 61.9(9) 2 3 ?
N21 C21 N21 61.9(9) . 3 ?
OW C21 H21D 90(8) 6_554 . ?
OW C21 H21D 151(6) 4_554 . ?
OW C21 H21D 72(5) 5_554 . ?
N21 C21 H21D 88(5) 11 . ?
N21 C21 H21D 28(8) 12 . ?
N21 C21 H21D 113(8) 10 . ?
C21 C21 H21D 106(7) 7 . ?
N21 C21 H21D 39(8) 2 . ?
N21 C21 H21D 100(8) . . ?
N21 C21 H21D 87(5) 3 . ?
OW C21 H21E 67(6) 6_554 . ?
OW C21 H21E 112(4) 4_554 . ?
OW C21 H21E 140(7) 5_554 . ?
N21 C21 H21E 18(7) 11 . ?
N21 C21 H21E 93(5) 12 . ?
N21 C21 H21E 102(7) 10 . ?
C21 C21 H21E 112(6) 7 . ?
N21 C21 H21E 82(5) 2 . ?
N21 C21 H21E 95(7) . . ?
N21 C21 H21E 34(6) 3 . ?
H21D C21 H21E 87.4(2) . . ?
C21 OW C21 85(2) 10 4 ?
C21 OW OW 50.4(8) 10 2 ?
C21 OW OW 50.4(8) 4 2 ?
C21 OW OW 50.4(8) 10 3 ?
C21 OW OW 50.4(8) 4 3 ?
OW OW OW 60.0 2 3 ?
C21 OW N21 133.6(19) 10 7_556 ?
C21 OW N21 52.6(8) 4 7_556 ?
OW OW N21 84.6(14) 2 7_556 ?
OW OW N21 101.0(8) 3 7_556 ?
C21 OW N21 52.6(8) 10 2 ?
C21 OW N21 133.6(19) 4 2 ?
OW OW N21 101.0(8) 2 2 ?
OW OW N21 84.6(14) 3 2 ?
N21 OW N21 174(2) 7_556 2 ?
C21 OW HW1 58(7) 10 . ?
C21 OW HW1 27(6) 4 . ?
OW OW HW1 33(3) 2 . ?
OW OW HW1 33(3) 3 . ?
N21 OW HW1 78(5) 7_556 . ?
N21 OW HW1 108(7) 2 . ?
C21 OW HW2 144(10) 10 . ?
C21 OW HW2 83(8) 4 . ?
OW OW HW2 97(10) 2 . ?
OW OW HW2 134(10) 3 . ?
N21 OW HW2 33(10) 7_556 . ?
N21 OW HW2 142(10) 2 . ?
HW1 OW HW2 106(4) . . ?

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
Ni0 O1 C1 O1 179.32(19) . . . 7_556 ?
N21 N21 C21 OW 93(11) 10 . . 6_554 ?
C21 N21 C21 OW -70(4) 10 . . 6_554 ?
OW N21 C21 OW -87(5) 3 . . 6_554 ?
N21 N21 C21 OW -34(4) 3 . . 6_554 ?
N21 N21 C21 OW -105(4) 2 . . 6_554 ?
N21 N21 C21 OW -118(3) 12 . . 6_554 ?
N21 N21 C21 OW -29(3) 11 . . 6_554 ?
N21 N21 C21 OW 7(11) 10 . . 4_554 ?
C21 N21 C21 OW -156.0(16) 10 . . 4_554 ?
OW N21 C21 OW -174(3) 3 . . 4_554 ?
N21 N21 C21 OW -120.4(16) 3 . . 4_554 ?
N21 N21 C21 OW 168.3(16) 2 . . 4_554 ?
N21 N21 C21 OW 155.3(16) 12 . . 4_554 ?
N21 N21 C21 OW -115.4(16) 11 . . 4_554 ?
N21 N21 C21 OW -77(12) 10 . . 5_554 ?
C21 N21 C21 OW 120.4(18) 10 . . 5_554 ?
OW N21 C21 OW 103(3) 3 . . 5_554 ?
N21 N21 C21 OW 156.1(18) 3 . . 5_554 ?
N21 N21 C21 OW 84.8(17) 2 . . 5_554 ?
N21 N21 C21 OW 71.8(19) 12 . . 5_554 ?
N21 N21 C21 OW 161(2) 11 . . 5_554 ?
N21 N21 C21 N21 122(10) 10 . . 11 ?
C21 N21 C21 N21 -41(3) 10 . . 11 ?
OW N21 C21 N21 -58(4) 3 . . 11 ?
N21 N21 C21 N21 -5(3) 3 . . 11 ?
N21 N21 C21 N21 -76(3) 2 . . 11 ?
N21 N21 C21 N21 -89.3(9) 12 . . 11 ?
N21 N21 C21 N21 -149(10) 10 . . 12 ?
C21 N21 C21 N21 49(3) 10 . . 12 ?
OW N21 C21 N21 31(4) 3 . . 12 ?
N21 N21 C21 N21 84(3) 3 . . 12 ?
N21 N21 C21 N21 13(3) 2 . . 12 ?
N21 N21 C21 N21 89.3(9) 11 . . 12 ?
C21 N21 C21 N21 -163(13) 10 . . 10 ?
OW N21 C21 N21 179(14) 3 . . 10 ?
N21 N21 C21 N21 -127(13) 3 . . 10 ?
N21 N21 C21 N21 162(13) 2 . . 10 ?
N21 N21 C21 N21 149(10) 12 . . 10 ?
N21 N21 C21 N21 -122(10) 11 . . 10 ?
N21 N21 C21 C21 -17(13) 10 . . 7 ?
C21 N21 C21 C21 180.000(9) 10 . . 7 ?
OW N21 C21 C21 162.3(14) 3 . . 7 ?
N21 N21 C21 C21 -144.34(19) 3 . . 7 ?
N21 N21 C21 C21 144.34(19) 2 . . 7 ?
N21 N21 C21 C21 131(3) 12 . . 7 ?
N21 N21 C21 C21 -139(3) 11 . . 7 ?
N21 N21 C21 N21 -162(13) 10 . . 2 ?
C21 N21 C21 N21 35.66(19) 10 . . 2 ?
OW N21 C21 N21 17.9(15) 3 . . 2 ?
N21 N21 C21 N21 71.3(4) 3 . . 2 ?
N21 N21 C21 N21 -13(3) 12 . . 2 ?
N21 N21 C21 N21 76(3) 11 . . 2 ?
N21 N21 C21 N21 127(13) 10 . . 3 ?
C21 N21 C21 N21 -35.66(19) 10 . . 3 ?
OW N21 C21 N21 -53.4(13) 3 . . 3 ?
N21 N21 C21 N21 -71.3(4) 2 . . 3 ?
N21 N21 C21 N21 -84(3) 12 . . 3 ?
N21 N21 C21 N21 5(3) 11 . . 3 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O1 1.02(6) 2.57(2) 3.130(3) 114.1(12) 3_665
C1 H1 O1 1.02(6) 2.57(2) 3.130(3) 114.1(12) 9_666
C1 H1 OW 1.02(6) 2.54(6) 3.56(2) 180.000(4) 2_665
N21 H21A OW 0.92 1.49 2.339(19) 152.4 .
N21 H21A OW 0.92 1.26 2.04(2) 139.2 2
N21 H21B O1 0.89 2.00 2.80(3) 150.1 3
N21 H21C O1 0.91 2.50 3.17(4) 131.4 .
N21 H21C O1 0.91 2.21 2.95(3) 138.2 12
C21 H21D O1 0.9700(14) 2.48(9) 3.221(2) 133(9) 11
C21 H21D N21 0.9700(14) 1.13(12) 1.705(19) 109(10) 2
C21 H21D OW 0.9700(14) 2.67(11) 3.035(16) 103(8) .
OW HW1 N21 0.841(14) 2.15(8) 2.76(2) 130(7) 5
OW HW1 N21 0.841(14) 1.67(7) 2.339(19) 135(7) 9_556
OW HW2 O1 0.841(14) 2.4(3) 2.785(11) 106(22) 2
OW HW2 O1 0.841(14) 2.7(3) 3.194(2) 121(26) 9_556

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_5_Zn_eda
_database_code_depnum_ccdc_archive 'CCDC 1537668'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 N2 O13 Zn2'
_chemical_formula_weight         480.98

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   13.9580(2)
_cell_length_b                   13.9580(2)
_cell_length_c                   22.4646(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3790.32(13)
_cell_formula_units_Z            9
_cell_measurement_temperature    295
_cell_measurement_reflns_used    13340
_cell_measurement_theta_min      2.919
_cell_measurement_theta_max      25.990

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_F_000             2196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    2.917
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.922
_oxdiff_exptl_absorpt_empirical_full_max 1.199
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean 10.4508
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13340
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.919
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.853
_reflns_number_total             2817
_reflns_number_gt                2781
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_max     0.704
_reflns_Friedel_fraction_full    0.714

_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+88.5486P] 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     SHELXL
_refine_ls_extinction_coef       0.0038(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.089(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2817
_refine_ls_number_parameters     285
_refine_ls_number_restraints     167
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.259
_refine_ls_restrained_S_all      1.967
_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
Zn0 Zn -0.00883(12) 0.3324(2) -0.00038(7) 0.0150(4) Uani 1 1 d . . . . .
Zn1 Zn 0.3333 0.6667 0.15700(12) 0.0151(7) Uani 1 3 d S T P . .
Zn2 Zn 0.0000 0.0000 0.1654(2) 0.0163(5) Uani 1 3 d S T P . .
Zn3 Zn -0.3333 0.3333 0.17573(12) 0.0150(7) Uani 1 3 d S T P . .
O1 O 0.0603(7) 0.4818(7) 0.0466(4) 0.0221(19) Uani 1 1 d . . . . .
O2 O 0.1885(7) 0.6061(7) 0.1065(5) 0.026(2) Uani 1 1 d . . . . .
O3 O 0.0693(8) 0.2688(8) 0.0544(5) 0.035(2) Uani 1 1 d . . . . .
O4 O 0.0751(8) 0.1449(7) 0.1127(6) 0.035(3) Uani 1 1 d . . . . .
O5 O -0.1500(8) 0.2590(8) 0.0552(5) 0.044(3) Uani 1 1 d . . . . .
O6 O -0.2630(7) 0.2610(7) 0.1231(5) 0.028(2) Uani 1 1 d . . . . .
O7 O -0.0894(7) 0.1844(7) -0.0481(4) 0.0215(19) Uani 1 1 d . . . . .
O8 O -0.0858(7) 0.0586(7) -0.1061(5) 0.024(2) Uani 1 1 d . . . . .
O9 O -0.0820(9) 0.4046(9) -0.0532(5) 0.040(3) Uani 1 1 d . U . . .
O10 O -0.1916(7) 0.4061(7) -0.1223(5) 0.026(2) Uani 1 1 d . . . . .
O11 O 0.1267(8) 0.3955(8) -0.0587(5) 0.033(2) Uani 1 1 d . . . . .
O12 O 0.2586(7) 0.5215(7) -0.1171(5) 0.029(2) Uani 1 1 d . . . . .
C1 C 0.1445(10) 0.5184(11) 0.0778(7) 0.029(3) Uani 1 1 d . . . . .
H1 H 0.1785 0.4757 0.0799 0.035 Uiso 1 1 calc R U . . .
C2 C 0.0260(10) 0.1793(11) 0.0791(6) 0.027(3) Uani 1 1 d . . . . .
H2 H -0.0493 0.1324 0.0729 0.033 Uiso 1 1 calc R U . . .
C3 C -0.1822(9) 0.3059(9) 0.0895(7) 0.025(3) Uani 1 1 d . . . . .
H3 H -0.1416 0.3827 0.0901 0.030 Uiso 1 1 calc R U . . .
C4 C -0.0436(10) 0.1447(10) -0.0774(7) 0.028(3) Uani 1 1 d . . . . .
H4 H 0.0333 0.1852 -0.0778 0.034 Uiso 1 1 calc R U . . .
C5 C -0.1538(9) 0.3608(9) -0.0916(6) 0.019(3) Uani 1 1 d . . . . .
H5 H -0.1821 0.2856 -0.0979 0.023 Uiso 1 1 calc R U . . .
C6 C 0.1778(11) 0.4878(11) -0.0808(7) 0.028(3) Uani 1 1 d . . . . .
H6 H 0.1557 0.5382 -0.0700 0.033 Uiso 1 1 calc R U . . .
N21A N -0.0714(16) 0.6005(16) -0.0185(10) 0.025(4) Uani 0.62 1 d . U P A 1
H21A H -0.0529 0.6174 0.0195 0.037 Uiso 0.62 1 calc R U P A 1
H21B H -0.0861 0.5316 -0.0254 0.037 Uiso 0.62 1 calc R U P A 1
H21C H -0.1309 0.6058 -0.0267 0.037 Uiso 0.62 1 calc R U P A 1
N22A N 0.0748(15) 0.7369(15) -0.1612(9) 0.031(4) Uani 0.62 1 d . U P A 1
H22A H 0.0568 0.7206 -0.1994 0.046 Uiso 0.62 1 calc R U P A 1
H22B H 0.1394 0.7409 -0.1542 0.046 Uiso 0.62 1 calc R U P A 1
H22C H 0.0801 0.8018 -0.1529 0.046 Uiso 0.62 1 calc R U P A 1
C21A C 0.0223(19) 0.6786(19) -0.0572(11) 0.028(4) Uani 0.62 1 d . U P A 1
H21D H 0.0872 0.6724 -0.0488 0.034 Uiso 0.62 1 calc R U P A 1
H21E H 0.0403 0.7540 -0.0489 0.034 Uiso 0.62 1 calc R U P A 1
C22A C -0.0105(17) 0.6510(19) -0.1239(12) 0.029(4) Uani 0.62 1 d . U P A 1
H22D H -0.0182 0.5798 -0.1336 0.035 Uiso 0.62 1 calc R U P A 1
H22E H -0.0810 0.6470 -0.1310 0.035 Uiso 0.62 1 calc R U P A 1
OWA O 0.0637(13) 0.7008(13) 0.0803(8) 0.029(3) Uani 0.62 1 d D U P B 1
HW1A H 0.111(13) 0.685(16) 0.092(8) 0.035 Uiso 0.62 1 d D U P C 1
HW2A H 0.057(17) 0.737(17) 0.108(6) 0.035 Uiso 0.62 1 d D U P D 1
N21B N -0.063(2) 0.599(2) 0.0151(14) 0.016(4) Uani 0.38 1 d . U P E 2
H21F H -0.0406 0.6229 -0.0217 0.024 Uiso 0.38 1 calc R U P E 2
H21G H -0.1318 0.5862 0.0200 0.024 Uiso 0.38 1 calc R U P E 2
H21H H -0.0621 0.5363 0.0210 0.024 Uiso 0.38 1 calc R U P E 2
N22B N 0.076(3) 0.746(3) 0.1569(15) 0.036(6) Uani 0.38 1 d . U P E 2
H22F H 0.0595 0.7290 0.1951 0.055 Uiso 0.38 1 calc R U P E 2
H22G H 0.0809 0.8109 0.1493 0.055 Uiso 0.38 1 calc R U P E 2
H22H H 0.1403 0.7500 0.1487 0.055 Uiso 0.38 1 calc R U P E 2
C21B C 0.014(3) 0.686(3) 0.0599(17) 0.026(5) Uani 0.38 1 d . U P E 2
H21I H 0.0884 0.7008 0.0524 0.031 Uiso 0.38 1 calc R U P E 2
H21J H 0.0132 0.7541 0.0515 0.031 Uiso 0.38 1 calc R U P E 2
C22B C -0.008(3) 0.663(3) 0.1211(18) 0.026(5) Uani 0.38 1 d . U P E 2
H22I H -0.0142 0.5923 0.1299 0.031 Uiso 0.38 1 calc R U P E 2
H22J H -0.0784 0.6579 0.1307 0.031 Uiso 0.38 1 calc R U P E 2
OWB O 0.036(2) 0.732(2) -0.0816(12) 0.026(4) Uani 0.38 1 d D U P F 2
HW1B H 0.01(3) 0.74(3) -0.112(9) 0.031 Uiso 0.38 1 d D U P G 2
HW2B H 0.104(7) 0.76(3) -0.074(18) 0.031 Uiso 0.38 1 d D U P H 2


_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
Zn0 O7 2.087(9) . ?
Zn0 O1 2.093(9) . ?
Zn0 O11 2.100(9) . ?
Zn0 O3 2.112(9) . ?
Zn0 O5 2.115(9) . ?
Zn0 O9 2.119(9) . ?
Zn1 O2 2.093(9) . ?
Zn1 O2 2.093(9) 3_565 ?
Zn1 O2 2.093(9) 2_665 ?
Zn1 O10 2.099(9) 4 ?
Zn1 O10 2.099(9) 6_455 ?
Zn1 O10 2.099(9) 5_565 ?
Zn2 O12 2.093(9) 5 ?
Zn2 O12 2.093(9) 4_445 ?
Zn2 O12 2.093(9) 6_455 ?
Zn2 O4 2.115(9) 2 ?
Zn2 O4 2.115(9) . ?
Zn2 O4 2.115(9) 3 ?
Zn3 O6 2.090(9) 3_455 ?
Zn3 O6 2.090(9) 2_565 ?
Zn3 O6 2.091(9) . ?
Zn3 O8 2.102(9) 6_455 ?
Zn3 O8 2.102(9) 5_455 ?
Zn3 O8 2.102(9) 4_455 ?
O1 C1 1.238(15) . ?
O2 C1 1.241(15) . ?
O3 C2 1.217(16) . ?
O4 C2 1.264(17) . ?
O5 C3 1.230(15) . ?
O6 C3 1.237(15) . ?
O7 C4 1.227(15) . ?
O8 C4 1.225(15) . ?
O8 Zn3 2.102(9) 7_544 ?
O9 C5 1.229(15) . ?
O10 C5 1.221(14) . ?
O10 Zn1 2.099(9) 7_444 ?
O11 C6 1.223(15) . ?
O12 C6 1.276(16) . ?
O12 Zn2 2.093(9) 7_554 ?
N21A C21A 1.49(3) . ?
N22A C22A 1.46(3) . ?
C21A C22A 1.56(3) . ?
N21B C21B 1.53(5) . ?
N22B C22B 1.42(5) . ?
C21B C22B 1.41(5) . ?

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
O7 Zn0 O1 175.3(3) . . ?
O7 Zn0 O11 91.2(4) . . ?
O1 Zn0 O11 91.6(4) . . ?
O7 Zn0 O3 91.1(4) . . ?
O1 Zn0 O3 92.7(4) . . ?
O11 Zn0 O3 89.6(4) . . ?
O7 Zn0 O5 85.0(3) . . ?
O1 Zn0 O5 92.2(4) . . ?
O11 Zn0 O5 176.2(4) . . ?
O3 Zn0 O5 90.3(5) . . ?
O7 Zn0 O9 91.9(4) . . ?
O1 Zn0 O9 84.3(4) . . ?
O11 Zn0 O9 89.9(4) . . ?
O3 Zn0 O9 177.0(4) . . ?
O5 Zn0 O9 90.4(4) . . ?
O2 Zn1 O2 93.4(4) . 3_565 ?
O2 Zn1 O2 93.4(4) . 2_665 ?
O2 Zn1 O2 93.4(4) 3_565 2_665 ?
O2 Zn1 O10 174.2(3) . 4 ?
O2 Zn1 O10 84.7(4) 3_565 4 ?
O2 Zn1 O10 92.2(4) 2_665 4 ?
O2 Zn1 O10 92.2(4) . 6_455 ?
O2 Zn1 O10 174.2(3) 3_565 6_455 ?
O2 Zn1 O10 84.7(4) 2_665 6_455 ?
O10 Zn1 O10 89.9(4) 4 6_455 ?
O2 Zn1 O10 84.7(4) . 5_565 ?
O2 Zn1 O10 92.2(4) 3_565 5_565 ?
O2 Zn1 O10 174.2(3) 2_665 5_565 ?
O10 Zn1 O10 89.9(4) 4 5_565 ?
O10 Zn1 O10 89.9(4) 6_455 5_565 ?
O12 Zn2 O12 93.1(4) 5 4_445 ?
O12 Zn2 O12 93.1(4) 5 6_455 ?
O12 Zn2 O12 93.1(4) 4_445 6_455 ?
O12 Zn2 O4 179.0(5) 5 2 ?
O12 Zn2 O4 87.7(4) 4_445 2 ?
O12 Zn2 O4 87.5(3) 6_455 2 ?
O12 Zn2 O4 87.5(3) 5 . ?
O12 Zn2 O4 179.0(5) 4_445 . ?
O12 Zn2 O4 87.7(4) 6_455 . ?
O4 Zn2 O4 91.7(5) 2 . ?
O12 Zn2 O4 87.7(4) 5 3 ?
O12 Zn2 O4 87.5(3) 4_445 3 ?
O12 Zn2 O4 179.0(5) 6_455 3 ?
O4 Zn2 O4 91.7(5) 2 3 ?
O4 Zn2 O4 91.7(5) . 3 ?
O6 Zn3 O6 91.2(4) 3_455 2_565 ?
O6 Zn3 O6 91.2(4) 3_455 . ?
O6 Zn3 O6 91.2(4) 2_565 . ?
O6 Zn3 O8 174.4(3) 3_455 6_455 ?
O6 Zn3 O8 84.3(4) 2_565 6_455 ?
O6 Zn3 O8 92.2(4) . 6_455 ?
O6 Zn3 O8 92.2(4) 3_455 5_455 ?
O6 Zn3 O8 174.4(3) 2_565 5_455 ?
O6 Zn3 O8 84.3(4) . 5_455 ?
O8 Zn3 O8 92.6(4) 6_455 5_455 ?
O6 Zn3 O8 84.3(4) 3_455 4_455 ?
O6 Zn3 O8 92.2(4) 2_565 4_455 ?
O6 Zn3 O8 174.4(3) . 4_455 ?
O8 Zn3 O8 92.6(4) 6_455 4_455 ?
O8 Zn3 O8 92.6(4) 5_455 4_455 ?
C1 O1 Zn0 124.5(8) . . ?
C1 O2 Zn1 125.6(8) . . ?
C2 O3 Zn0 127.0(9) . . ?
C2 O4 Zn2 126.4(8) . . ?
C3 O5 Zn0 127.7(8) . . ?
C3 O6 Zn3 129.1(8) . . ?
C4 O7 Zn0 125.3(8) . . ?
C4 O8 Zn3 125.7(8) . 7_544 ?
C5 O9 Zn0 128.6(8) . . ?
C5 O10 Zn1 128.5(8) . 7_444 ?
C6 O11 Zn0 128.5(9) . . ?
C6 O12 Zn2 128.8(8) . 7_554 ?
O1 C1 O2 126.9(12) . . ?
O3 C2 O4 125.2(12) . . ?
O5 C3 O6 126.6(11) . . ?
O8 C4 O7 128.5(12) . . ?
O10 C5 O9 126.6(11) . . ?
O11 C6 O12 126.1(12) . . ?
N21A C21A C22A 109.7(19) . . ?
N22A C22A C21A 109.4(17) . . ?
C22B C21B N21B 118(3) . . ?
C21B C22B N22B 112(3) . . ?

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
Zn0 O1 C1 O2 -179.9(11) . . . . ?
Zn1 O2 C1 O1 -178.4(11) . . . . ?
Zn0 O3 C2 O4 -178.4(11) . . . . ?
Zn2 O4 C2 O3 171.3(11) . . . . ?
Zn0 O5 C3 O6 -177.4(11) . . . . ?
Zn3 O6 C3 O5 -172.8(11) . . . . ?
Zn3 O8 C4 O7 177.6(11) 7_544 . . . ?
Zn0 O7 C4 O8 179.8(11) . . . . ?
Zn1 O10 C5 O9 -167.0(11) 7_444 . . . ?
Zn0 O9 C5 O10 -177.8(10) . . . . ?
Zn0 O11 C6 O12 -178.5(11) . . . . ?
Zn2 O12 C6 O11 168.6(11) 7_554 . . . ?
N21A C21A C22A N22A 172.0(17) . . . . ?
N21B C21B C22B N22B 174(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O3 0.93 2.57 3.140(15) 120.3 .
C2 H2 O4 0.93 2.60 3.170(16) 119.8 2
C3 H3 O1 0.93 2.63 3.178(14) 118.4 .
C4 H4 O8 0.93 2.62 3.183(15) 119.2 3
C4 H4 O11 0.93 2.58 3.124(15) 117.6 .
C5 H5 O7 0.93 2.60 3.168(14) 120.1 .
N21A H21A OWA 0.89 1.99 2.79(3) 148.9 .
N21A H21B O9 0.89 1.91 2.77(2) 164.2 .
N21A H21C O5 0.89 2.50 3.05(2) 120.1 2_565
N21A H21C O7 0.89 2.21 2.96(2) 142.6 2_565
N22A H22A OWA 0.89 1.90 2.67(3) 143.8 9_454
N22A H22B O12 0.89 1.91 2.78(2) 164.2 3_565
N22A H22C O6 0.89 2.24 2.91(2) 132.1 7_554
N22A H22C O8 0.89 2.62 3.29(2) 132.7 2_565
C21A H21D O11 0.97 2.69 3.14(3) 109.0 3_565
C21A H21D O12 0.97 2.63 3.30(2) 126.5 3_565
C22A H22D O10 0.97 2.44 3.07(2) 122.8 .
OWA HW1A O2 0.840(14) 1.91(6) 2.726(18) 162(17) .
OWA HW2A N22A 0.840(14) 2.1(2) 2.67(3) 125(20) 5_565
N21B H21F OWB 0.89 1.91 2.74(4) 155.4 .
N21B H21H O1 0.89 2.26 2.99(3) 138.9 .
N21B H21H O9 0.89 2.39 3.01(3) 126.6 .
N22B H22H O2 0.89 2.60 3.26(4) 132.1 .

_refine_diff_density_max         0.714
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.137

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_3_Co_eda
_database_code_depnum_ccdc_archive 'CCDC 1551125'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-06-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_SYMMS02_3_Co_eda            
;
PROBLEM: Cell angle alpha should be 90 for a trigonal/hexagonal
RESPONSE: The cell is rhombohedral
;
_vrf_PLAT112_3_Co_eda            
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem.        2        100 %Fit
RESPONSE: Type of disorder excludes additional symmetry
;
_vrf_PLAT113_3_Co_eda            
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        R32 Check
RESPONSE: Type of disorder excludes additional symmetry
;
# Added during the CSD deposition process: Friday 19 May 2017 08:31 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H18 Co2 N2 O13'
_chemical_formula_weight         468.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :R'
_space_group_name_Hall           'P 3*'

_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'
'z, x, y'
'y, z, x'

_cell_length_a                   10.9975(2)
_cell_length_b                   10.9975(2)
_cell_length_c                   10.9975(2)
_cell_angle_alpha                78.85
_cell_angle_beta                 78.85
_cell_angle_gamma                78.85
_cell_volume                     1263.38(7)
_cell_formula_units_Z            3
_cell_measurement_temperature    295
_cell_measurement_reflns_used    15513
_cell_measurement_theta_min      2.917
_cell_measurement_theta_max      29.575

_exptl_crystal_description       irregular
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_F_000             714
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.041
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_method       ω--scan
_diffrn_detector_area_resol_mean 10.4508
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15513
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.917
_diffrn_reflns_theta_max         29.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_point_group_measured_fraction_full 0.918
_reflns_number_total             3857
_reflns_number_gt                3403
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.675
_reflns_Friedel_fraction_full    0.842

_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       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  ?

_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)+9.5899P] 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     SHELXL
_refine_ls_extinction_coef       0.0160(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1247 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.051(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3857
_refine_ls_number_parameters     285
_refine_ls_number_restraints     161
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.122
_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
Co0 Co 0.2716(3) 0.9264(3) 0.6000(4) 0.0144(3) Uani 1 1 d . . . . .
Co1 Co 0.4258(3) 0.4258(3) 0.4258(3) 0.0137(6) Uani 1 3 d S T P . .
Co2 Co -0.2280(3) 0.7720(3) 0.7720(3) 0.0175(8) Uani 1 3 d S T P . .
Co3 Co 0.0984(4) 1.0984(4) 0.0984(4) 0.0138(4) Uani 1 3 d S T P . .
O1 O 0.3638(8) 0.8028(7) 0.4742(9) 0.037(2) Uani 1 1 d . . . . .
O2 O 0.4088(9) 0.6209(8) 0.4049(8) 0.0309(19) Uani 1 1 d . . . . .
O3 O 0.1550(7) 0.7990(8) 0.6973(7) 0.0253(16) Uani 1 1 d . . . . .
O4 O -0.0322(7) 0.7407(8) 0.7635(8) 0.0317(19) Uani 1 1 d . . . . .
O5 O 0.1420(8) 1.0092(9) 0.4794(7) 0.0334(19) Uani 1 1 d . . . . .
O6 O 0.0787(8) 1.0740(9) 0.2940(8) 0.0324(19) Uani 1 1 d . . . . .
O7 O 0.1828(9) 1.0597(8) 0.7174(7) 0.0340(19) Uani 1 1 d . . . . .
O8 O 0.1139(9) 1.1221(8) 0.9001(8) 0.032(2) Uani 1 1 d . . . . .
O9 O 0.4000(8) 1.0438(7) 0.5005(7) 0.0257(16) Uani 1 1 d . . . . .
O10 O 0.4587(7) 1.2307(7) 0.4364(7) 0.0247(16) Uani 1 1 d . . . . .
O11 O 0.3925(7) 0.8399(8) 0.7292(9) 0.041(2) Uani 1 1 d . . . . .
O12 O 0.5767(7) 0.7868(9) 0.7930(8) 0.032(2) Uani 1 1 d . . . . .
C1 C 0.3557(10) 0.6895(9) 0.4821(10) 0.023(2) Uani 1 1 d . . . . .
H1 H 0.3051 0.6539 0.5526 0.027 Uiso 1 1 calc R U . . .
C2 C 0.0387(10) 0.8158(11) 0.7082(12) 0.035(3) Uani 1 1 d . . . . .
H2 H 0.0008 0.8934 0.6706 0.042 Uiso 1 1 calc R U . . .
C3 C 0.1611(11) 1.0304(11) 0.3628(10) 0.031(2) Uani 1 1 d . . . . .
H3 H 0.2436 1.0125 0.3228 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1659(10) 1.0414(10) 0.8340(10) 0.025(2) Uani 1 1 d . . . . .
H4 H 0.1943 0.9615 0.8746 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3838(10) 1.1595(9) 0.4945(11) 0.027(2) Uani 1 1 d . . . . .
H5 H 0.3086 1.1966 0.5374 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5071(9) 0.8377(11) 0.7155(10) 0.026(2) Uani 1 1 d . . . . .
H6 H 0.5447 0.8784 0.6393 0.031 Uiso 1 1 calc R U . . .
N21A N 0.5851(15) 0.8418(16) 0.3141(16) 0.041(4) Uani 0.7 1 d . U P A 1
H21A H 0.6233 0.8956 0.3376 0.062 Uiso 0.7 1 calc R U P A 1
H21B H 0.6395 0.7723 0.3018 0.062 Uiso 0.7 1 calc R U P A 1
H21C H 0.5214 0.8225 0.3738 0.062 Uiso 0.7 1 calc R U P A 1
N22A N 0.4406(15) 0.8430(15) 0.0343(13) 0.038(3) Uani 0.7 1 d . U P A 1
H22A H 0.4039 0.7856 0.0147 0.056 Uiso 0.7 1 calc R U P A 1
H22B H 0.5085 0.8550 -0.0226 0.056 Uiso 0.7 1 calc R U P A 1
H22C H 0.3871 0.9149 0.0350 0.056 Uiso 0.7 1 calc R U P A 1
C21A C 0.5405(18) 0.8955(19) 0.2048(18) 0.037(3) Uani 0.7 1 d . U P A 1
H21D H 0.6092 0.9206 0.1408 0.045 Uiso 0.7 1 calc R U P A 1
H21E H 0.4795 0.9700 0.2185 0.045 Uiso 0.7 1 calc R U P A 1
C22A C 0.477(2) 0.799(2) 0.158(2) 0.045(3) Uani 0.7 1 d . U P A 1
H22D H 0.5351 0.7209 0.1565 0.054 Uiso 0.7 1 calc R U P A 1
H22E H 0.4030 0.7824 0.2188 0.054 Uiso 0.7 1 calc R U P A 1
OWA O 0.6506(14) 1.0797(14) 0.3136(13) 0.045(3) Uani 0.7 1 d D U P B 1
HWA1 H 0.585(11) 1.129(12) 0.337(17) 0.054 Uiso 0.7 1 d D U P C 1
HWA2 H 0.644(18) 1.011(10) 0.362(17) 0.054 Uiso 0.7 1 d D U P D 1
N21B N 0.608(3) 0.893(3) 0.352(3) 0.027(5) Uani 0.3 1 d . U P E 2
H21F H 0.5719 0.8734 0.2943 0.040 Uiso 0.3 1 calc R U P E 2
H21G H 0.5493 0.9125 0.4167 0.040 Uiso 0.3 1 calc R U P E 2
H21H H 0.6630 0.8271 0.3790 0.040 Uiso 0.3 1 calc R U P E 2
N22B N 0.769(3) 1.170(3) 0.353(3) 0.022(5) Uani 0.3 1 d . U P E 2
H22F H 0.8078 1.1836 0.4113 0.033 Uiso 0.3 1 calc R U P E 2
H22G H 0.7036 1.2307 0.3423 0.033 Uiso 0.3 1 calc R U P E 2
H22H H 0.8220 1.1688 0.2805 0.033 Uiso 0.3 1 calc R U P E 2
C22B C 0.721(4) 1.040(4) 0.395(4) 0.036(5) Uani 0.3 1 d . U P E 2
H22I H 0.7906 0.9766 0.4200 0.044 Uiso 0.3 1 calc R U P E 2
H22J H 0.6563 1.0454 0.4678 0.044 Uiso 0.3 1 calc R U P E 2
C21B C 0.672(4) 0.999(4) 0.299(4) 0.034(5) Uani 0.3 1 d . U P E 2
H21I H 0.6141 1.0678 0.2612 0.041 Uiso 0.3 1 calc R U P E 2
H21J H 0.7405 0.9756 0.2328 0.041 Uiso 0.3 1 calc R U P E 2
OWB O 0.551(2) 0.889(2) 0.126(2) 0.037(4) Uani 0.3 1 d D U P F 2
HWB1 H 0.527(17) 0.965(2) 0.097(9) 0.045 Uiso 0.3 1 d D U P G 2
HWB2 H 0.543(11) 0.848(4) 0.072(5) 0.045 Uiso 0.3 1 d D U P H 2


_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
Co0 O3 2.082(7) . ?
Co0 O5 2.092(7) . ?
Co0 O11 2.100(7) . ?
Co0 O9 2.102(7) . ?
Co0 O1 2.107(7) . ?
Co0 O7 2.112(8) . ?
Co1 O2 2.089(7) . ?
Co1 O2 2.089(7) 3 ?
Co1 O2 2.089(7) 2 ?
Co1 O10 2.090(7) 3_455 ?
Co1 O10 2.090(7) 1_545 ?
Co1 O10 2.090(7) 2_554 ?
Co2 O12 2.093(7) 3_455 ?
Co2 O12 2.093(7) 1_455 ?
Co2 O12 2.093(7) 2_455 ?
Co2 O4 2.100(7) . ?
Co2 O4 2.100(7) 2_465 ?
Co2 O4 2.100(7) 3_456 ?
Co3 O6 2.089(7) 2_564 ?
Co3 O6 2.089(7) . ?
Co3 O6 2.089(7) 3_465 ?
Co3 O8 2.123(7) 1_554 ?
Co3 O8 2.123(7) 2_464 ?
Co3 O8 2.123(7) 3_455 ?
O1 C1 1.252(11) . ?
O2 C1 1.231(11) . ?
O3 C2 1.242(12) . ?
O4 C2 1.238(12) . ?
O5 C3 1.243(12) . ?
O6 C3 1.258(13) . ?
O7 C4 1.242(12) . ?
O8 C4 1.239(13) . ?
O8 Co3 2.123(7) 1_556 ?
O9 C5 1.242(12) . ?
O10 C5 1.245(12) . ?
O10 Co1 2.090(7) 1_565 ?
O11 C6 1.236(12) . ?
O12 C6 1.236(12) . ?
O12 Co2 2.093(7) 1_655 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N21A C21A 1.37(2) . ?
N21A H21A 0.8900 . ?
N21A H21B 0.8900 . ?
N21A H21C 0.8900 . ?
N22A C22A 1.46(3) . ?
N22A H22A 0.8900 . ?
N22A H22B 0.8900 . ?
N22A H22C 0.8900 . ?
C21A C22A 1.58(2) . ?
C21A H21D 0.9700 . ?
C21A H21E 0.9700 . ?
C22A H22D 0.9700 . ?
C22A H22E 0.9700 . ?
OWA HWA1 0.843(14) . ?
OWA HWA2 0.843(14) . ?
N21B C21B 1.45(6) . ?
N21B H21F 0.8900 . ?
N21B H21G 0.8900 . ?
N21B H21H 0.8900 . ?
N22B C22B 1.57(5) . ?
N22B H22F 0.8900 . ?
N22B H22G 0.8900 . ?
N22B H22H 0.8900 . ?
C22B C21B 1.46(5) . ?
C22B H22I 0.9700 . ?
C22B H22J 0.9700 . ?
C21B H21I 0.9700 . ?
C21B H21J 0.9700 . ?
OWB HWB1 0.8400(14) . ?
OWB HWB2 0.8400(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Co0 O5 91.7(3) . . ?
O3 Co0 O11 85.2(3) . . ?
O5 Co0 O11 176.5(3) . . ?
O3 Co0 O9 175.8(3) . . ?
O5 Co0 O9 91.0(3) . . ?
O11 Co0 O9 92.2(3) . . ?
O3 Co0 O1 92.2(3) . . ?
O5 Co0 O1 90.9(3) . . ?
O11 Co0 O1 90.7(4) . . ?
O9 Co0 O1 84.5(3) . . ?
O3 Co0 O7 91.1(3) . . ?
O5 Co0 O7 87.6(3) . . ?
O11 Co0 O7 90.9(4) . . ?
O9 Co0 O7 92.2(3) . . ?
O1 Co0 O7 176.4(3) . . ?
O2 Co1 O2 91.4(3) . 3 ?
O2 Co1 O2 91.4(3) . 2 ?
O2 Co1 O2 91.4(3) 3 2 ?
O2 Co1 O10 91.3(3) . 3_455 ?
O2 Co1 O10 174.8(3) 3 3_455 ?
O2 Co1 O10 84.1(3) 2 3_455 ?
O2 Co1 O10 174.8(3) . 1_545 ?
O2 Co1 O10 84.1(3) 3 1_545 ?
O2 Co1 O10 91.3(3) 2 1_545 ?
O10 Co1 O10 93.4(3) 3_455 1_545 ?
O2 Co1 O10 84.1(3) . 2_554 ?
O2 Co1 O10 91.3(3) 3 2_554 ?
O2 Co1 O10 174.8(3) 2 2_554 ?
O10 Co1 O10 93.4(3) 3_455 2_554 ?
O10 Co1 O10 93.4(3) 1_545 2_554 ?
O12 Co2 O12 90.7(4) 3_455 1_455 ?
O12 Co2 O12 90.7(4) 3_455 2_455 ?
O12 Co2 O12 90.7(4) 1_455 2_455 ?
O12 Co2 O4 92.6(4) 3_455 . ?
O12 Co2 O4 174.4(3) 1_455 . ?
O12 Co2 O4 84.8(3) 2_455 . ?
O12 Co2 O4 84.8(3) 3_455 2_465 ?
O12 Co2 O4 92.6(3) 1_455 2_465 ?
O12 Co2 O4 174.4(3) 2_455 2_465 ?
O4 Co2 O4 92.2(4) . 2_465 ?
O12 Co2 O4 174.4(3) 3_455 3_456 ?
O12 Co2 O4 84.8(3) 1_455 3_456 ?
O12 Co2 O4 92.6(3) 2_455 3_456 ?
O4 Co2 O4 92.2(4) . 3_456 ?
O4 Co2 O4 92.2(4) 2_465 3_456 ?
O6 Co3 O6 93.4(3) 2_564 . ?
O6 Co3 O6 93.4(3) 2_564 3_465 ?
O6 Co3 O6 93.4(3) . 3_465 ?
O6 Co3 O8 88.0(3) 2_564 1_554 ?
O6 Co3 O8 178.6(4) . 1_554 ?
O6 Co3 O8 87.0(3) 3_465 1_554 ?
O6 Co3 O8 178.6(4) 2_564 2_464 ?
O6 Co3 O8 87.0(3) . 2_464 ?
O6 Co3 O8 88.0(3) 3_465 2_464 ?
O8 Co3 O8 91.7(3) 1_554 2_464 ?
O6 Co3 O8 87.0(3) 2_564 3_455 ?
O6 Co3 O8 88.0(3) . 3_455 ?
O6 Co3 O8 178.6(4) 3_465 3_455 ?
O8 Co3 O8 91.7(3) 1_554 3_455 ?
O8 Co3 O8 91.7(3) 2_464 3_455 ?
C1 O1 Co0 127.8(7) . . ?
C1 O2 Co1 127.8(7) . . ?
C2 O3 Co0 126.0(7) . . ?
C2 O4 Co2 125.3(7) . . ?
C3 O5 Co0 128.0(7) . . ?
C3 O6 Co3 128.6(7) . . ?
C4 O7 Co0 126.3(7) . . ?
C4 O8 Co3 125.4(7) . 1_556 ?
C5 O9 Co0 125.1(7) . . ?
C5 O10 Co1 124.8(6) . 1_565 ?
C6 O11 Co0 127.3(7) . . ?
C6 O12 Co2 128.2(7) . 1_655 ?
O2 C1 O1 125.9(9) . . ?
O2 C1 H1 117.0 . . ?
O1 C1 H1 117.0 . . ?
O4 C2 O3 127.1(10) . . ?
O4 C2 H2 116.4 . . ?
O3 C2 H2 116.4 . . ?
O5 C3 O6 125.7(10) . . ?
O5 C3 H3 117.2 . . ?
O6 C3 H3 117.2 . . ?
O8 C4 O7 124.6(10) . . ?
O8 C4 H4 117.7 . . ?
O7 C4 H4 117.7 . . ?
O9 C5 O10 126.1(9) . . ?
O9 C5 H5 116.9 . . ?
O10 C5 H5 116.9 . . ?
O12 C6 O11 126.4(9) . . ?
O12 C6 H6 116.8 . . ?
O11 C6 H6 116.8 . . ?
C21A N21A H21A 109.5 . . ?
C21A N21A H21B 109.5 . . ?
H21A N21A H21B 109.5 . . ?
C21A N21A H21C 109.5 . . ?
H21A N21A H21C 109.5 . . ?
H21B N21A H21C 109.5 . . ?
C22A N22A H22A 109.5 . . ?
C22A N22A H22B 109.5 . . ?
H22A N22A H22B 109.5 . . ?
C22A N22A H22C 109.5 . . ?
H22A N22A H22C 109.5 . . ?
H22B N22A H22C 109.5 . . ?
N21A C21A C22A 110.3(16) . . ?
N21A C21A H21D 109.6 . . ?
C22A C21A H21D 109.6 . . ?
N21A C21A H21E 109.6 . . ?
C22A C21A H21E 109.6 . . ?
H21D C21A H21E 108.1 . . ?
N22A C22A C21A 114.1(15) . . ?
N22A C22A H22D 108.7 . . ?
C21A C22A H22D 108.7 . . ?
N22A C22A H22E 108.7 . . ?
C21A C22A H22E 108.7 . . ?
H22D C22A H22E 107.6 . . ?
HWA1 OWA HWA2 105(4) . . ?
C21B N21B H21F 109.5 . . ?
C21B N21B H21G 109.5 . . ?
H21F N21B H21G 109.5 . . ?
C21B N21B H21H 109.5 . . ?
H21F N21B H21H 109.5 . . ?
H21G N21B H21H 109.5 . . ?
C22B N22B H22F 109.5 . . ?
C22B N22B H22G 109.5 . . ?
H22F N22B H22G 109.5 . . ?
C22B N22B H22H 109.5 . . ?
H22F N22B H22H 109.5 . . ?
H22G N22B H22H 109.5 . . ?
C21B C22B N22B 114(3) . . ?
C21B C22B H22I 108.7 . . ?
N22B C22B H22I 108.7 . . ?
C21B C22B H22J 108.7 . . ?
N22B C22B H22J 108.7 . . ?
H22I C22B H22J 107.6 . . ?
N21B C21B C22B 110(3) . . ?
N21B C21B H21I 109.6 . . ?
C22B C21B H21I 109.6 . . ?
N21B C21B H21J 109.6 . . ?
C22B C21B H21J 109.6 . . ?
H21I C21B H21J 108.1 . . ?
HWB1 OWB HWB2 105.8(4) . . ?

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 O1 168.2(9) . . . . ?
Co0 O1 C1 O2 178.0(9) . . . . ?
Co2 O4 C2 O3 -177.2(10) . . . . ?
Co0 O3 C2 O4 178.6(10) . . . . ?
Co0 O5 C3 O6 175.7(9) . . . . ?
Co3 O6 C3 O5 -174.1(9) . . . . ?
Co3 O8 C4 O7 -174.2(8) 1_556 . . . ?
Co0 O7 C4 O8 179.6(8) . . . . ?
Co0 O9 C5 O10 179.8(9) . . . . ?
Co1 O10 C5 O9 178.7(9) 1_565 . . . ?
Co2 O12 C6 O11 176.6(9) 1_655 . . . ?
Co0 O11 C6 O12 179.6(9) . . . . ?
N21A C21A C22A N22A -172.8(15) . . . . ?
N22B C22B C21B N21B -168(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O3 0.93 2.60 3.159(12) 119.3 .
C2 H2 O4 0.93 2.59 3.153(13) 119.3 2_465
C2 H2 O5 0.93 2.63 3.146(13) 115.6 .
C4 H4 O8 0.93 2.59 3.160(12) 119.8 3_456
C5 H5 O7 0.93 2.59 3.147(12) 119.1 .
C6 H6 O12 0.93 2.65 3.150(12) 114.4 3
N21A H21A OWA 0.89 2.06 2.84(2) 145.9 .
N21A H21B O3 0.89 2.29 3.026(17) 140.5 3
N21A H21B O11 0.89 2.52 3.052(18) 119.1 3
N21A H21C O1 0.89 1.89 2.768(18) 167.2 .
N22A H22A OWA 0.89 1.89 2.67(2) 145.1 2_554
N22A H22B O4 0.89 2.55 3.224(17) 133.4 3
N22A H22B O12 0.89 2.24 2.899(16) 130.5 1_554
N22A H22C O6 0.89 1.97 2.839(17) 163.9 2_564
C21A H21E O5 0.97 2.68 3.17(2) 111.4 2_564
C21A H21E O6 0.97 2.77 3.43(2) 125.4 2_564
C22A H22E O2 0.97 2.44 3.08(2) 123.3 .
OWA HWA1 O10 0.843(14) 1.91(7) 2.728(16) 162(21) .
OWA HWA2 N21A 0.843(14) 2.3(2) 2.84(2) 125(22) .
N21B H21F OWB 0.89 1.88 2.69(4) 150.6 .
N21B H21G O1 0.89 2.48 3.02(3) 118.9 .
N21B H21G O9 0.89 2.15 2.96(3) 150.6 .
N21B H21H O11 0.89 2.05 2.88(3) 154.6 3
N22B H22G O10 0.89 2.69 3.33(3) 129.2 .
C22B H22I O12 0.97 2.39 3.10(4) 129.4 3
OWB HWB1 O6 0.8400(14) 2.66(15) 3.24(3) 128(15) 2_564

_refine_diff_density_max         0.697
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.130

_shelxl_version_number           2013-4

