# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_sp_coznkgec
_database_code_depnum_ccdc_archive 'CCDC 1883551'
loop_
_audit_author_name
_audit_author_address
'Horst Puschmann'
;Durham University 
United Kingdom
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2015-10-07
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2015.09.07 svn.r3215 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 Co N4 O12'
_chemical_formula_sum            'C16 H22 Co N4 O12'
_chemical_formula_weight         521.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16CoN4O12
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.6210(2)
_cell_length_b                   9.05593(12)
_cell_length_c                   11.20988(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.0872(10)
_cell_angle_gamma                90
_cell_volume                     2081.56(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22533
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.5460
_cell_measurement_theta_min      2.4560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1076
_exptl_crystal_recrystallization_method 
'The material was recrystallised from water by slow evaporation'
_exptl_crystal_size_max          0.6063
_exptl_crystal_size_mid          0.2714
_exptl_crystal_size_min          0.2263
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            52185
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.737
_diffrn_reflns_theta_min         3.000
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.4992   38.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00   18.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.4992  -19.0000  -60.0000 117

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.4992   57.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega   -6.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242 -122.0000 -131.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega   15.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242 -154.0000   69.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242 -178.0000 -180.0000 72

#__ type_ start__ end____ width___ exp.time_
  7 omega  -42.00   48.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242  -57.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega  -95.00   -5.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.4992  -57.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
  9 omega   -3.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242   77.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
 10 omega    6.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242   57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   -3.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242   77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
 12 omega   35.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242  178.0000  150.0000 68

#__ type_ start__ end____ width___ exp.time_
 13 omega   -3.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 14 omega  -95.00   -5.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.4992  -57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 15 omega  -46.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242    0.0000 -150.0000 146

#__ type_ start__ end____ width___ exp.time_
 16 omega    2.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242   38.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
 17 omega  -46.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242    0.0000 -180.0000 146

#__ type_ start__ end____ width___ exp.time_
 18 omega    6.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242   57.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
 19 omega    6.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242   57.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
 20 omega  -46.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1242    0.0000 -120.0000 146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0004793000
_diffrn_orient_matrix_UB_12      -0.0565898000
_diffrn_orient_matrix_UB_13      0.0436272000
_diffrn_orient_matrix_UB_21      -0.0344009000
_diffrn_orient_matrix_UB_22      0.0065016000
_diffrn_orient_matrix_UB_23      -0.0024845000
_diffrn_orient_matrix_UB_31      -0.0036588000
_diffrn_orient_matrix_UB_32      -0.0537332000
_diffrn_orient_matrix_UB_33      -0.0462625000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           35
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3552
_reflns_number_total             3735
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0308P)²+2.6088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.55354(2) 0.2500 0.01045(6) Uani 1 2 d S T P . .
O1 O 0.57337(4) 0.40441(9) 0.22227(6) 0.01693(14) Uani 1 1 d . . . . .
O2 O 0.66677(4) 0.30677(9) 0.30715(7) 0.01915(15) Uani 1 1 d . . . . .
O3 O 0.45733(4) 0.72141(9) 0.36018(7) 0.01705(14) Uani 1 1 d . . . . .
O4 O 0.47382(4) 0.81926(9) 0.54735(7) 0.01660(14) Uani 1 1 d . . . . .
O5 O 0.70710(5) 0.69214(12) 0.34504(11) 0.0359(2) Uani 1 1 d . . . . .
O6 O 0.81085(4) 0.61683(10) 0.36614(8) 0.02233(17) Uani 1 1 d . . . . .
H6 H 0.8165(9) 0.688(2) 0.3065(18) 0.041(5) Uiso 1 1 d . . . . .
N1 N 0.56238(4) 0.56448(9) 0.40591(7) 0.01230(14) Uani 1 1 d . . . . .
N2 N 0.54642(4) 0.66224(10) 0.49065(7) 0.01348(15) Uani 1 1 d . . . . .
H2 H 0.5707 0.6773 0.5590 0.016 Uiso 1 1 calc R . . . .
C1 C 0.61998(5) 0.39185(11) 0.30650(8) 0.01349(16) Uani 1 1 d . . . . .
C2 C 0.61604(4) 0.49141(11) 0.41505(8) 0.01211(16) Uani 1 1 d . . . . .
C3 C 0.48908(5) 0.73441(11) 0.45893(8) 0.01320(16) Uani 1 1 d . . . . .
C5 C 0.41773(5) 0.91833(12) 0.52211(10) 0.01774(18) Uani 1 1 d . . . . .
H5A H 0.3773 0.8609 0.5012 0.021 Uiso 1 1 calc R . . . .
H5B H 0.4243 0.9852 0.4546 0.021 Uiso 1 1 calc R . . . .
C6 C 0.41361(5) 1.00521(13) 0.63582(11) 0.0207(2) Uani 1 1 d . . . . .
H6A H 0.3794 1.0802 0.6221 0.031 Uiso 1 1 calc GR . . . .
H6B H 0.4555 1.0535 0.6594 0.031 Uiso 1 1 calc GR . . . .
H6C H 0.4032 0.9384 0.6999 0.031 Uiso 1 1 calc GR . . . .
C21 C 0.66857(5) 0.49751(12) 0.51824(8) 0.01428(16) Uani 1 1 d . . . . .
H21A H 0.6632 0.4118 0.5711 0.017 Uiso 1 1 calc R . . . .
H21B H 0.6622 0.5879 0.5653 0.017 Uiso 1 1 calc R . . . .
C22 C 0.73857(5) 0.49716(12) 0.48419(9) 0.01533(17) Uani 1 1 d . . . . .
H22A H 0.7691 0.5154 0.5570 0.018 Uiso 1 1 calc R . . . .
H22B H 0.7485 0.3985 0.4528 0.018 Uiso 1 1 calc R . . . .
C23 C 0.74936(5) 0.61223(12) 0.39136(9) 0.01667(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.0760(8) 2_655 ?
Co1 O1 2.0759(8) . ?
Co1 O3 2.2004(8) 2_655 ?
Co1 O3 2.2003(8) . ?
Co1 N1 2.0597(8) . ?
Co1 N1 2.0596(8) 2_655 ?
O1 C1 1.2790(12) . ?
O2 C1 1.2341(12) . ?
O3 C3 1.2305(12) . ?
O4 C3 1.3184(12) . ?
O4 C5 1.4674(12) . ?
O5 C23 1.2069(13) . ?
O6 H6 0.94(2) . ?
O6 C23 1.3288(12) . ?
N1 N2 1.3640(11) . ?
N1 C2 1.2841(12) . ?
N2 H2 0.8800 . ?
N2 C3 1.3648(12) . ?
C1 C2 1.5235(13) . ?
C2 C21 1.4996(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5080(15) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5318(13) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5057(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 Co1 O1 98.84(5) . 2_655 ?
O1 Co1 O3 151.01(3) 2_655 2_655 ?
O1 Co1 O3 91.39(3) . 2_655 ?
O1 Co1 O3 151.01(3) . . ?
O1 Co1 O3 91.39(3) 2_655 . ?
O3 Co1 O3 92.60(4) . 2_655 ?
N1 Co1 O1 107.69(3) 2_655 . ?
N1 Co1 O1 76.04(3) 2_655 2_655 ?
N1 Co1 O1 107.68(3) . 2_655 ?
N1 Co1 O1 76.04(3) . . ?
N1 Co1 O3 75.01(3) 2_655 2_655 ?
N1 Co1 O3 75.01(3) . . ?
N1 Co1 O3 101.08(3) 2_655 . ?
N1 Co1 O3 101.08(3) . 2_655 ?
N1 Co1 N1 174.49(5) 2_655 . ?
C1 O1 Co1 116.74(6) . . ?
C3 O3 Co1 111.39(6) . . ?
C3 O4 C5 117.22(8) . . ?
C23 O6 H6 111.3(12) . . ?
N2 N1 Co1 116.55(6) . . ?
C2 N1 Co1 119.89(7) . . ?
C2 N1 N2 123.26(8) . . ?
N1 N2 H2 123.3 . . ?
N1 N2 C3 113.31(8) . . ?
C3 N2 H2 123.3 . . ?
O1 C1 C2 115.94(8) . . ?
O2 C1 O1 125.85(9) . . ?
O2 C1 C2 118.21(9) . . ?
N1 C2 C1 111.09(8) . . ?
N1 C2 C21 126.04(9) . . ?
C21 C2 C1 122.86(8) . . ?
O3 C3 O4 125.84(9) . . ?
O3 C3 N2 123.52(9) . . ?
O4 C3 N2 110.64(8) . . ?
O4 C5 H5A 110.6 . . ?
O4 C5 H5B 110.6 . . ?
O4 C5 C6 105.66(8) . . ?
H5A C5 H5B 108.7 . . ?
C6 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C21 H21A 108.4 . . ?
C2 C21 H21B 108.4 . . ?
C2 C21 C22 115.49(8) . . ?
H21A C21 H21B 107.5 . . ?
C22 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C21 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 C21 112.52(8) . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
O5 C23 O6 123.46(10) . . ?
O5 C23 C22 124.02(10) . . ?
O6 C23 C22 112.52(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 O2 178.21(8) . . . . ?
Co1 O1 C1 C2 -1.42(11) . . . . ?
Co1 O3 C3 O4 -175.70(8) . . . . ?
Co1 O3 C3 N2 5.22(12) . . . . ?
Co1 N1 N2 C3 2.30(10) . . . . ?
Co1 N1 C2 C1 -6.32(11) . . . . ?
Co1 N1 C2 C21 174.83(7) . . . . ?
O1 C1 C2 N1 4.97(12) . . . . ?
O1 C1 C2 C21 -176.14(9) . . . . ?
O2 C1 C2 N1 -174.70(9) . . . . ?
O2 C1 C2 C21 4.20(14) . . . . ?
N1 N2 C3 O3 -5.28(14) . . . . ?
N1 N2 C3 O4 175.52(8) . . . . ?
N1 C2 C21 C22 -139.48(10) . . . . ?
N2 N1 C2 C1 -179.80(8) . . . . ?
N2 N1 C2 C21 1.35(15) . . . . ?
C1 C2 C21 C22 41.80(13) . . . . ?
C2 N1 N2 C3 175.99(9) . . . . ?
C2 C21 C22 C23 50.99(12) . . . . ?
C3 O4 C5 C6 -177.61(9) . . . . ?
C5 O4 C3 O3 -6.61(15) . . . . ?
C5 O4 C3 N2 172.57(8) . . . . ?
C21 C22 C23 O5 -2.81(16) . . . . ?
C21 C22 C23 O6 176.90(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 0 0 0.1267 0.9998 0.0000 -0.0002 -0.0005 -0.0344 -0.0037
-1 0 0 0.0997 -0.9998 -0.0000 0.0002 0.0005 0.0344 0.0037
2 -4 -5 0.1992 2.0086 -4.0016 -5.0012 0.0073 -0.0827 0.4390
-2 4 5 0.1992 -2.0086 4.0016 5.0012 -0.0073 0.0827 -0.4390
-3 5 0 0.1171 -3.0045 5.0001 -0.0002 -0.2815 0.1359 -0.2577
3 -5 0 0.1171 3.0045 -5.0001 0.0002 0.2815 -0.1359 0.2577
0 -1 -1 0.1994 0.0020 -1.0003 -1.0001 0.0130 -0.0041 0.1000
0 1 1 0.1994 -0.0020 1.0003 1.0001 -0.0130 0.0041 -0.1000
-5 4 -5 0.2065 -4.9981 3.9985 -5.0011 -0.4421 0.2104 0.0348
5 -4 5 0.2065 4.9981 -3.9985 5.0011 0.4421 -0.2104 -0.0348
5 2 -2 0.1692 4.9987 1.9996 -2.0016 -0.2029 -0.1540 -0.0331
-5 -2 2 0.1692 -4.9987 -1.9996 2.0016 0.2029 0.1540 0.0331
5 4 0 0.1452 4.9947 4.0003 -0.0013 -0.2288 -0.1458 -0.2332
-5 -4 0 0.1452 -4.9947 -4.0003 0.0013 0.2288 0.1458 0.2332
-5 -4 -5 0.2089 -4.9898 -4.0018 -5.0001 0.0107 0.1581 0.4646
5 4 5 0.2089 4.9898 4.0018 5.0001 -0.0107 -0.1581 -0.4646

_olex2_date_sample_data_collection 2015-10-06
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 700 PlusSeries'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id CoZnKGEC
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sp_znkgec
_database_code_depnum_ccdc_archive 'CCDC 1883552'
loop_
_audit_author_name
_audit_author_address
'Horst Puschmann'
;Durham University
United Kingdom
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2015-10-05
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2015.09.07 svn.r3215 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 N4 O12 Zn'
_chemical_formula_sum            'C16 H22 N4 O12 Zn'
_chemical_formula_weight         527.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H22N4O12Zn
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.6603(9)
_cell_length_b                   9.0466(4)
_cell_length_c                   11.1969(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.230(4)
_cell_angle_gamma                90
_cell_volume                     2080.40(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4267
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.7550
_cell_measurement_theta_min      2.9770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0972
1 0 0 0.0972
-1 0 1 0.2556
1 0 -1 0.2556
5 -3 0 0.1279
-5 3 0 0.1279
-2 -1 5 0.2466
2 1 -5 0.2466
-1 -1 0 0.1386
1 1 0 0.1386

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.309
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0008 0.0001 -0.0005 0.0019 -0.0344 -0.0030
1.0008 -0.0001 0.0005 -0.0019 0.0344 0.0030
-1.0032 0.0005 0.9984 0.0095 -0.0218 -0.0649
1.0032 -0.0005 -0.9984 -0.0095 0.0218 0.0649
5.0027 -2.9970 0.0007 -0.2421 0.1620 -0.0157
-5.0027 2.9970 -0.0007 0.2421 -0.1620 0.0157
-2.0141 -0.9967 4.9929 -0.0357 -0.0090 -0.3257
2.0141 0.9967 -4.9929 0.0357 0.0090 0.3257
-1.0013 -0.9988 -0.0012 -0.0757 -0.0377 -0.0133
1.0013 0.9988 0.0012 0.0757 0.0377 0.0133

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7565
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        27.496
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         3.002
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0756
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00 -35.00   1.00    4.00    --  -18.25-178.00-150.00   59
  2  ω    -24.00  24.00   1.00    4.00    --  -18.25-100.00  60.00   48
  3  ω    -91.00  26.00   1.00    4.00    --  -18.25 -19.00  60.00  117
  4  ω    -24.00  24.00   1.00    4.00    --  -18.25-100.00-150.00   48
  5  ω    -50.00  29.00   1.00    4.00    --   18.72 -57.00  30.00   79
  6  ω    -51.00 -26.00   1.00    4.00    --   18.72 -77.00 150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0018672000
_diffrn_orient_matrix_UB_12      0.0776736000
_diffrn_orient_matrix_UB_13      0.0076041000
_diffrn_orient_matrix_UB_21      0.0343397000
_diffrn_orient_matrix_UB_22      0.0032650000
_diffrn_orient_matrix_UB_23      0.0127096000
_diffrn_orient_matrix_UB_31      0.0030429000
_diffrn_orient_matrix_UB_32      0.0102965000
_diffrn_orient_matrix_UB_33      -0.0619476000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           35
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2214
_reflns_number_total             2352
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+2.5548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0619
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn 1.0000 0.54831(3) 0.7500 0.01062(8) Uani 1 2 d S T P . .
O1 O 1.04312(5) 0.71892(12) 0.63933(9) 0.0132(2) Uani 1 1 d . . . . .
O2 O 0.92613(5) 0.39988(12) 0.77636(9) 0.0125(2) Uani 1 1 d . . . . .
O3 O 0.83229(5) 0.30601(13) 0.69077(10) 0.0155(2) Uani 1 1 d . . . . .
O4 O 1.02577(5) 0.81961(12) 0.45289(9) 0.0132(2) Uani 1 1 d . . . . .
O5 O 0.68941(5) 0.61715(14) 0.63436(10) 0.0186(3) Uani 1 1 d . . . . .
H5 H 0.6861 0.6785 0.6897 0.028 Uiso 1 1 calc GR . . . .
O6 O 0.79327(6) 0.68982(16) 0.65736(13) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.93718(6) 0.56335(14) 0.59375(10) 0.0089(2) Uani 1 1 d . . . . .
N2 N 0.95334(6) 0.66239(14) 0.50984(11) 0.0105(3) Uani 1 1 d . . . . .
C1 C 1.01104(7) 0.73343(17) 0.54149(13) 0.0104(3) Uani 1 1 d . . . . .
C2 C 1.08209(7) 0.91829(18) 0.47773(15) 0.0148(3) Uani 1 1 d . . . . .
H2A H 1.1224 0.8604 0.4982 0.018 Uiso 1 1 calc R . . . .
H2B H 1.0759 0.9853 0.5455 0.018 Uiso 1 1 calc R . . . .
C3 C 1.08593(8) 1.00516(19) 0.36396(15) 0.0169(3) Uani 1 1 d . . . . .
H3A H 1.1204 1.0796 0.3774 0.025 Uiso 1 1 calc GR . . . .
H3B H 1.0442 1.0543 0.3409 0.025 Uiso 1 1 calc GR . . . .
H3C H 1.0957 0.9381 0.2996 0.025 Uiso 1 1 calc GR . . . .
C4 C 0.87950(7) 0.38985(17) 0.69234(12) 0.0101(3) Uani 1 1 d . . . . .
C5 C 0.88371(7) 0.49127(16) 0.58429(12) 0.0088(3) Uani 1 1 d . . . . .
C6 C 0.83113(7) 0.49882(18) 0.48106(13) 0.0112(3) Uani 1 1 d . . . . .
H6A H 0.8363 0.4136 0.4275 0.013 Uiso 1 1 calc R . . . .
H6B H 0.8376 0.5898 0.4346 0.013 Uiso 1 1 calc R . . . .
C7 C 0.76107(7) 0.49855(18) 0.51511(13) 0.0122(3) Uani 1 1 d . . . . .
H7A H 0.7306 0.5186 0.4424 0.015 Uiso 1 1 calc R . . . .
H7B H 0.7509 0.3993 0.5453 0.015 Uiso 1 1 calc R . . . .
C8 C 0.75088(7) 0.61201(18) 0.60951(14) 0.0135(3) Uani 1 1 d . . . . .
H2 H 0.9379(9) 0.660(2) 0.4405(18) 0.018(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn O1 2.2251(11) 2_756 y
Zn O1 2.2251(11) . y
Zn O2 2.0778(11) . y
Zn O2 2.0777(11) 2_756 y
Zn N1 2.0666(12) . y
Zn N1 2.0666(12) 2_756 y
O1 C1 1.2244(18) . ?
O2 C4 1.2746(18) . ?
O3 C4 1.2341(18) . ?
O4 C1 1.3229(18) . ?
O4 C2 1.4689(18) . ?
O5 H5 0.8400 . ?
O5 C8 1.3302(18) . ?
O6 C8 1.203(2) . ?
N1 N2 1.3657(17) . ?
N1 C5 1.2774(19) . ?
N2 C1 1.3667(19) . ?
N2 H2 0.81(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.506(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.528(2) . ?
C5 C6 1.4994(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5364(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.504(2) . ?

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 Zn O1 92.16(6) . 2_756 y
O2 Zn O1 91.40(4) . 2_756 y
O2 Zn O1 150.70(4) 2_756 2_756 y
O2 Zn O1 91.40(4) 2_756 . y
O2 Zn O1 150.70(4) . . y
O2 Zn O2 99.48(6) 2_756 . y
N1 Zn O1 74.66(4) . . y
N1 Zn O1 99.97(4) . 2_756 y
N1 Zn O1 74.66(4) 2_756 2_756 y
N1 Zn O1 99.97(4) 2_756 . y
N1 Zn O2 109.01(4) . 2_756 y
N1 Zn O2 76.07(4) . . y
N1 Zn O2 109.01(4) 2_756 . y
N1 Zn O2 76.07(4) 2_756 2_756 y
N1 Zn N1 172.45(7) . 2_756 y
C1 O1 Zn 111.23(9) . . ?
C4 O2 Zn 116.69(9) . . ?
C1 O4 C2 117.27(11) . . ?
C8 O5 H5 109.5 . . ?
N2 N1 Zn 116.60(9) . . ?
C5 N1 Zn 119.65(10) . . ?
C5 N1 N2 123.48(12) . . ?
N1 N2 C1 113.67(12) . . ?
N1 N2 H2 122.8(14) . . ?
C1 N2 H2 120.4(14) . . ?
O1 C1 O4 126.01(13) . . ?
O1 C1 N2 123.63(13) . . ?
O4 C1 N2 110.35(12) . . ?
O4 C2 H2A 110.6 . . ?
O4 C2 H2B 110.6 . . ?
O4 C2 C3 105.69(12) . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C5 115.98(12) . . ?
O3 C4 O2 125.95(14) . . ?
O3 C4 C5 118.06(13) . . ?
N1 C5 C4 111.33(12) . . ?
N1 C5 C6 126.05(13) . . ?
C6 C5 C4 122.61(12) . . ?
C5 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C5 C6 C7 115.59(12) . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 112.38(12) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
O5 C8 C7 112.36(13) . . ?
O6 C8 O5 123.49(15) . . ?
O6 C8 C7 124.16(14) . . ?

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
O5 H5 O3 0.84 1.84 2.6729(16) 172.6 4_656
N2 H2 O2 0.81(2) 1.91(2) 2.6737(16) 158.7(19) 6_565

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
Zn O1 C1 O4 -175.91(12) . . . . ?
Zn O1 C1 N2 5.18(18) . . . . ?
Zn O2 C4 O3 178.39(12) . . . . ?
Zn O2 C4 C5 -1.20(16) . . . . ?
Zn N1 N2 C1 2.32(15) . . . . ?
Zn N1 C5 C4 -5.96(16) . . . . ?
Zn N1 C5 C6 175.38(11) . . . . ?
O2 C4 C5 N1 4.62(18) . . . . ?
O2 C4 C5 C6 -176.66(13) . . . . ?
O3 C4 C5 N1 -175.01(13) . . . . ?
O3 C4 C5 C6 3.7(2) . . . . ?
N1 N2 C1 O1 -5.3(2) . . . . ?
N1 N2 C1 O4 175.65(11) . . . . ?
N1 C5 C6 C7 -139.65(15) . . . . ?
N2 N1 C5 C4 -179.70(12) . . . . ?
N2 N1 C5 C6 1.6(2) . . . . ?
C1 O4 C2 C3 -178.26(12) . . . . ?
C2 O4 C1 O1 -6.6(2) . . . . ?
C2 O4 C1 N2 172.44(12) . . . . ?
C4 C5 C6 C7 41.8(2) . . . . ?
C5 N1 N2 C1 176.25(13) . . . . ?
C5 C6 C7 C8 50.54(18) . . . . ?
C6 C7 C8 O5 176.66(13) . . . . ?
C6 C7 C8 O6 -3.2(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-05
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 700 Series'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id ZnKGEC
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.885
####################################################################### 
# 
# 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_nhindncke_0m
_database_code_depnum_ccdc_archive 'CCDC 1895080'
loop_
_audit_author_name
_audit_author_address
'Hung HuyNguyen'
;VNU University of Science, 19 Le Thanh Tong, Hanoi, Vietnam
Vietnam
;
_audit_update_record             
;
2019-02-01 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2019-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H22 Co0.67 N4 Ni0.33 O12'
_chemical_formula_sum            'C16 H22 Co0.66 N4 Ni0.33 O12'
_chemical_formula_weight         521.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.6312(8)
_cell_length_b                   9.2643(4)
_cell_length_c                   11.2605(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.7330(10)
_cell_angle_gamma                90
_cell_volume                     2141.50(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9636
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      28.311
_cell_measurement_theta_min      2.961
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.760
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0523 before and 0.0451 after correction. The Ratio of minimum to maximum transmission is 0.9541. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1077
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34629
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.960
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2440
_reflns_number_total             2671
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+2.2512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0697
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{Ni, Co}
3. Uiso/Uaniso restraints and constraints
Uanis(Ni) = Uanis(Co)
4. Others
 Fixed Sof: Ni(0.167) Co(0.333)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.500000 0.43641(3) 0.750000 0.02277(8) Uani 0.334 2 d S T P . .
Co Co 0.500000 0.43641(3) 0.750000 0.02277(8) Uani 0.666 2 d S T P . .
O1 O 0.42934(5) 0.58466(12) 0.78349(9) 0.0308(2) Uani 1 1 d . . . . .
N1 N 0.43897(5) 0.43194(12) 0.59862(9) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.38298(7) 0.60064(16) 0.70046(12) 0.0251(3) Uani 1 1 d . . . . .
O2 O 0.33756(5) 0.68630(13) 0.70108(10) 0.0392(3) Uani 1 1 d . . . . .
N2 N 0.45503(5) 0.33728(13) 0.51282(9) 0.0246(2) Uani 1 1 d . . . . .
H2 H 0.431700 0.324853 0.445945 0.030 Uiso 1 1 calc R . . . .
C2 C 0.38597(6) 0.50452(15) 0.59111(11) 0.0218(3) Uani 1 1 d . . . . .
O3 O 0.18989(6) 0.38000(16) 0.63400(13) 0.0487(3) Uani 1 1 d . . . . .
H3 H 0.185597 0.318172 0.684733 0.069(8) Uiso 1 1 calc GR . . . .
C3 C 0.33338(6) 0.50180(17) 0.48918(12) 0.0281(3) Uani 1 1 d . . . . .
H3A H 0.339255 0.416315 0.441687 0.034(5) Uiso 1 1 calc R . . . .
H3B H 0.338879 0.585094 0.438969 0.041 Uiso 1 1 calc R . . . .
O4 O 0.29256(7) 0.3086(2) 0.65874(18) 0.0813(6) Uani 1 1 d . . . . .
C4 C 0.26354(7) 0.50214(17) 0.52387(13) 0.0304(3) Uani 1 1 d . . . . .
H4A H 0.254403 0.595570 0.557324 0.037(5) Uiso 1 1 calc R . . . .
H4B H 0.233661 0.488483 0.452624 0.040(5) Uiso 1 1 calc R . . . .
O5 O 0.54257(5) 0.27438(12) 0.64250(9) 0.0316(2) Uani 1 1 d . . . . .
C5 C 0.25162(7) 0.38682(18) 0.61267(14) 0.0338(3) Uani 1 1 d . . . . .
O6 O 0.52693(5) 0.18276(12) 0.45530(9) 0.0332(2) Uani 1 1 d . . . . .
C6 C 0.51162(7) 0.26476(15) 0.54398(12) 0.0247(3) Uani 1 1 d . . . . .
C7 C 0.58282(8) 0.08542(18) 0.47872(16) 0.0372(4) Uani 1 1 d . . . . .
H7A H 0.576414 0.020968 0.544425 0.047(5) Uiso 1 1 calc R . . . .
H7B H 0.622514 0.140085 0.498703 0.056 Uiso 1 1 calc R . . . .
C8 C 0.58679(9) 0.00140(19) 0.36560(17) 0.0436(4) Uani 1 1 d . . . . .
H8A H 0.596840 0.065737 0.303170 0.065 Uiso 1 1 calc GR . . . .
H8B H 0.545755 -0.044844 0.343137 0.065 Uiso 1 1 calc GR . . . .
H8C H 0.620326 -0.070405 0.378201 0.065 Uiso 1 1 calc GR . . . .


_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
Ni O1 2.0649(10) 2_656 ?
Ni O1 2.0648(10) . ?
Ni N1 2.0159(11) . ?
Ni N1 2.0159(11) 2_656 ?
Ni O5 2.1685(10) 2_656 ?
Ni O5 2.1685(10) . ?
O1 C1 1.2777(17) . ?
N1 N2 1.3697(15) . ?
N1 C2 1.2793(17) . ?
C1 O2 1.2286(17) . ?
C1 C2 1.5258(18) . ?
N2 H2 0.8600 . ?
N2 C6 1.3622(17) . ?
C2 C3 1.4988(17) . ?
O3 H3 0.8200 . ?
O3 C5 1.3209(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5300(18) . ?
O4 C5 1.192(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.500(2) . ?
O5 C6 1.2268(17) . ?
O6 C6 1.3180(17) . ?
O6 C7 1.4669(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.502(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
O1 Ni O1 96.61(6) . 2_656 ?
O1 Ni O5 91.48(4) . 2_656 ?
O1 Ni O5 153.52(4) 2_656 2_656 ?
O1 Ni O5 153.52(4) . . ?
O1 Ni O5 91.48(4) 2_656 . ?
N1 Ni O1 104.59(4) 2_656 . ?
N1 Ni O1 77.02(4) 2_656 2_656 ?
N1 Ni O1 104.59(4) . 2_656 ?
N1 Ni O1 77.02(4) . . ?
N1 Ni N1 177.64(7) 2_656 . ?
N1 Ni O5 76.54(4) . . ?
N1 Ni O5 101.78(4) . 2_656 ?
N1 Ni O5 101.79(4) 2_656 . ?
N1 Ni O5 76.54(4) 2_656 2_656 ?
O5 Ni O5 92.39(6) 2_656 . ?
C1 O1 Ni 115.72(9) . . ?
N2 N1 Ni 115.78(8) . . ?
C2 N1 Ni 120.17(9) . . ?
C2 N1 N2 123.73(11) . . ?
O1 C1 C2 115.80(12) . . ?
O2 C1 O1 125.90(13) . . ?
O2 C1 C2 118.29(12) . . ?
N1 N2 H2 123.4 . . ?
C6 N2 N1 113.30(11) . . ?
C6 N2 H2 123.4 . . ?
N1 C2 C1 110.90(11) . . ?
N1 C2 C3 126.19(12) . . ?
C3 C2 C1 122.90(12) . . ?
C5 O3 H3 109.5 . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C2 C3 C4 115.63(11) . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.95(12) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C6 O5 Ni 110.60(9) . . ?
O3 C5 C4 112.36(13) . . ?
O4 C5 O3 123.10(16) . . ?
O4 C5 C4 124.54(14) . . ?
C6 O6 C7 117.50(12) . . ?
O5 C6 N2 123.53(12) . . ?
O5 C6 O6 125.76(13) . . ?
O6 C6 N2 110.69(11) . . ?
O6 C7 H7A 110.5 . . ?
O6 C7 H7B 110.5 . . ?
O6 C7 C8 105.94(13) . . ?
H7A C7 H7B 108.7 . . ?
C8 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nhindzckm_0m
_database_code_depnum_ccdc_archive 'CCDC 1905842'
loop_
_audit_author_name
_audit_author_address
'Hung HuyNguyen'
;VNU University of Science
Vietnam
;
_audit_update_record             
;
2019-03-26 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2019-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 Co0.67 N4 O12 Zn0.33'
_chemical_formula_sum            'C16 H22 Co0.66 N4 O12 Zn0.33'
_chemical_formula_weight         523.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.6689(5)
_cell_length_b                   9.2368(3)
_cell_length_c                   11.2492(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.7590(10)
_cell_angle_gamma                90
_cell_volume                     2136.80(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      2.966
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.755
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0739 before and 0.0537 after correction. The Ratio of minimum to maximum transmission is 0.8888. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23907
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_min         2.966
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2395
_reflns_number_total             2667
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+1.4492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Shared sites
{Co, Zn}
3. Uiso/Uaniso restraints and constraints
Uanis(Co) = Uanis(Zn)
4. Others
 Fixed Sof: Zn(0.167) Co(0.333)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn 0.500000 0.55170(3) 0.250000 0.02511(9) Uani 0.334 2 d S T P . .
Co Co 0.500000 0.55170(3) 0.250000 0.02511(9) Uani 0.666 2 d S T P . .
O1 O 0.57348(6) 0.40609(14) 0.22147(9) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.56260(6) 0.56526(13) 0.40435(10) 0.0240(2) Uani 1 1 d . . . . .
C1 C 0.61963(7) 0.39465(17) 0.30456(13) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.66586(6) 0.31105(14) 0.30593(11) 0.0421(3) Uani 1 1 d . . . . .
N2 N 0.54670(6) 0.66178(14) 0.48881(10) 0.0274(3) Uani 1 1 d . . . . .
H2 H 0.570421 0.676220 0.555022 0.033 Uiso 1 1 calc R . . . .
C2 C 0.61590(7) 0.49396(16) 0.41239(12) 0.0239(3) Uani 1 1 d . . . . .
O3 O 0.81033(6) 0.62086(18) 0.36411(13) 0.0508(4) Uani 1 1 d . . . . .
H3 H 0.813800 0.680191 0.310903 0.076 Uiso 1 1 calc GR . . . .
C3 C 0.66848(7) 0.5000(2) 0.51405(14) 0.0304(3) Uani 1 1 d . . . . .
H3A H 0.663556 0.417321 0.565538 0.037 Uiso 1 1 calc R . . . .
H3B H 0.662179 0.586498 0.560415 0.037 Uiso 1 1 calc R . . . .
O4 O 0.70723(8) 0.6881(2) 0.3387(2) 0.0828(7) Uani 1 1 d . . . . .
C4 C 0.73818(7) 0.5008(2) 0.47905(15) 0.0331(3) Uani 1 1 d . . . . .
H4A H 0.767939 0.518732 0.549792 0.040 Uiso 1 1 calc R . . . .
H4B H 0.748134 0.405992 0.448515 0.040 Uiso 1 1 calc R . . . .
O5 O 0.45781(6) 0.71991(13) 0.36135(10) 0.0356(3) Uani 1 1 d . . . . .
C5 C 0.74895(8) 0.6128(2) 0.38652(16) 0.0361(4) Uani 1 1 d . . . . .
O6 O 0.47510(6) 0.81702(13) 0.54657(10) 0.0355(3) Uani 1 1 d . . . . .
C6 C 0.48968(7) 0.73299(17) 0.45816(13) 0.0269(3) Uani 1 1 d . . . . .
C7 C 0.41868(8) 0.9128(2) 0.52366(17) 0.0385(4) Uani 1 1 d . . . . .
H7A H 0.379334 0.856651 0.504761 0.046 Uiso 1 1 calc R . . . .
H7B H 0.424274 0.977067 0.457268 0.046 Uiso 1 1 calc R . . . .
C8 C 0.41483(10) 0.9979(2) 0.63645(19) 0.0461(4) Uani 1 1 d . . . . .
H8A H 0.380586 1.068173 0.624170 0.069 Uiso 1 1 calc GR . . . .
H8B H 0.455436 1.046450 0.657453 0.069 Uiso 1 1 calc GR . . . .
H8C H 0.405993 0.933508 0.699825 0.069 Uiso 1 1 calc GR . . . .


_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
Co O1 2.0776(12) 2_655 ?
Co O1 2.0776(12) . ?
Co N1 2.0624(12) . ?
Co N1 2.0623(12) 2_655 ?
Co O5 2.2278(12) 2_655 ?
Co O5 2.2278(12) . ?
O1 C1 1.2712(18) . ?
N1 N2 1.3668(17) . ?
N1 C2 1.2790(19) . ?
C1 O2 1.2274(19) . ?
C1 C2 1.529(2) . ?
N2 H2 0.8600 . ?
N2 C6 1.3634(19) . ?
C2 C3 1.498(2) . ?
O3 H3 0.8200 . ?
O3 C5 1.320(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.531(2) . ?
O4 C5 1.194(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.500(2) . ?
O5 C6 1.2209(18) . ?
O6 C6 1.3201(18) . ?
O6 C7 1.466(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.501(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
O1 Co O1 99.31(7) . 2_655 ?
O1 Co O5 91.78(5) . 2_655 ?
O1 Co O5 150.68(4) 2_655 2_655 ?
O1 Co O5 150.67(4) . . ?
O1 Co O5 91.78(5) 2_655 . ?
N1 Co O1 108.41(4) 2_655 . ?
N1 Co O1 76.28(4) 2_655 2_655 ?
N1 Co O1 108.41(4) . 2_655 ?
N1 Co O1 76.28(4) . . ?
N1 Co N1 173.04(7) 2_655 . ?
N1 Co O5 74.47(4) . . ?
N1 Co O5 100.55(4) . 2_655 ?
N1 Co O5 100.55(4) 2_655 . ?
N1 Co O5 74.47(4) 2_655 2_655 ?
O5 Co O5 91.56(7) 2_655 . ?
C1 O1 Co 116.52(10) . . ?
N2 N1 Co 116.78(9) . . ?
C2 N1 Co 119.44(10) . . ?
C2 N1 N2 123.51(12) . . ?
O1 C1 C2 116.08(13) . . ?
O2 C1 O1 125.97(14) . . ?
O2 C1 C2 117.95(13) . . ?
N1 N2 H2 123.2 . . ?
C6 N2 N1 113.63(12) . . ?
C6 N2 H2 123.2 . . ?
N1 C2 C1 111.38(12) . . ?
N1 C2 C3 126.07(13) . . ?
C3 C2 C1 122.53(13) . . ?
C5 O3 H3 109.5 . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C2 C3 C4 115.67(12) . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.99(13) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C6 O5 Co 111.34(10) . . ?
O3 C5 C4 112.57(14) . . ?
O4 C5 O3 123.07(17) . . ?
O4 C5 C4 124.35(16) . . ?
C6 O6 C7 117.39(13) . . ?
O5 C6 N2 123.59(14) . . ?
O5 C6 O6 125.92(14) . . ?
O6 C6 N2 110.48(12) . . ?
O6 C7 H7A 110.5 . . ?
O6 C7 H7B 110.5 . . ?
O6 C7 C8 106.03(15) . . ?
H7A C7 H7B 108.7 . . ?
C8 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_kgec
_database_code_depnum_ccdc_archive 'CCDC 1895072'
loop_
_audit_author_name
_audit_author_address
'Hung HuyNguyen'
;VNU University of Science, 19 Le Thanh Tong, Hanoi, Vietnam
Vietnam
;
_audit_update_record             
;
2019-02-01 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_audit_creation_date             2019-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H12 N2 O6, H2 O'
_chemical_formula_sum            'C8 H14 N2 O7'
_chemical_formula_weight         250.21
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.2750(12)
_cell_length_b                   5.8287(4)
_cell_length_c                   12.9351(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.532(2)
_cell_angle_gamma                90
_cell_volume                     1146.29(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      28.221
_cell_measurement_theta_min      2.978
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0854 before and 0.0587 after correction. The Ratio of minimum to maximum transmission is 0.9427. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39316
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         3.165
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2223
_reflns_number_total             2842
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.3130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1106
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O8(H8D,H8E)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.27963(8) -0.0672(2) 0.14787(10) 0.0590(3) Uani 1 1 d . . . . .
H1 H 0.315462 0.012009 0.183079 0.088 Uiso 1 1 calc GR . . . .
C1 C 0.20008(10) 0.0100(2) 0.15660(11) 0.0400(3) Uani 1 1 d . . . . .
O2 O 0.13683(8) -0.0739(2) 0.10553(9) 0.0566(3) Uani 1 1 d . . . . .
N2 N 0.26094(7) 0.30177(18) 0.26285(8) 0.0312(2) Uani 1 1 d . . . . .
C2 C 0.18850(8) 0.2049(2) 0.22928(9) 0.0293(3) Uani 1 1 d . . . . .
O3 O 0.11626(7) -0.17494(17) 0.35149(8) 0.0415(3) Uani 1 1 d . . . . .
N3 N 0.25823(7) 0.48837(19) 0.32514(9) 0.0345(3) Uani 1 1 d . . . . .
H3 H 0.208985 0.546709 0.339003 0.041 Uiso 1 1 calc R . . . .
C3 C 0.09767(8) 0.2666(2) 0.25487(10) 0.0317(3) Uani 1 1 d . . . . .
H3A H 0.055148 0.176527 0.211570 0.038 Uiso 1 1 calc R . . . .
H3B H 0.086830 0.427084 0.238509 0.038 Uiso 1 1 calc R . . . .
O4 O 0.11631(9) -0.0228(2) 0.50987(8) 0.0526(3) Uani 1 1 d . . . . .
H4 H 0.129889 -0.153692 0.528223 0.079 Uiso 1 1 calc GR . . . .
C4 C 0.08378(9) 0.2254(2) 0.36909(10) 0.0332(3) Uani 1 1 d . . . . .
H4A H 0.119024 0.335006 0.411418 0.040 Uiso 1 1 calc R . . . .
H4B H 0.022553 0.254474 0.378634 0.040 Uiso 1 1 calc R . . . .
C5 C 0.10712(8) -0.0122(2) 0.40729(10) 0.0310(3) Uani 1 1 d . . . . .
O6 O 0.40840(6) 0.5018(2) 0.35324(9) 0.0481(3) Uani 1 1 d . . . . .
C6 C 0.33674(9) 0.5804(2) 0.36512(10) 0.0349(3) Uani 1 1 d . . . . .
O7 O 0.32061(6) 0.76385(18) 0.42013(8) 0.0442(3) Uani 1 1 d . . . . .
C7 C 0.39522(10) 0.8691(3) 0.47999(12) 0.0526(4) Uani 1 1 d . . . . .
H7A H 0.436898 0.926684 0.434247 0.063 Uiso 1 1 calc R . . . .
H7B H 0.424886 0.758142 0.527068 0.063 Uiso 1 1 calc R . . . .
C8 C 0.35974(14) 1.0598(3) 0.53900(15) 0.0654(5) Uani 1 1 d . . . . .
H8A H 0.329649 1.166561 0.491503 0.098 Uiso 1 1 calc GR . . . .
H8B H 0.407187 1.136525 0.579064 0.098 Uiso 1 1 calc GR . . . .
H8C H 0.319366 0.999924 0.584693 0.098 Uiso 1 1 calc GR . . . .
O8 O 0.43293(8) 0.0722(2) 0.24597(11) 0.0618(3) Uani 1 1 d . . . . .
H8D H 0.426671 0.204647 0.275320 0.093 Uiso 1 1 d G . . . .
H8E H 0.479456 0.074812 0.212136 0.093 Uiso 1 1 d G . . . .


_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
O1 H1 0.8200 . ?
O1 C1 1.3108(19) . ?
C1 O2 1.2191(19) . ?
C1 C2 1.4959(18) . ?
N2 C2 1.2803(16) . ?
N2 N3 1.3566(15) . ?
C2 C3 1.5007(17) . ?
O3 C5 1.2082(16) . ?
N3 H3 0.8600 . ?
N3 C6 1.3689(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5316(17) . ?
O4 H4 0.8200 . ?
O4 C5 1.3221(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5018(18) . ?
O6 C6 1.2102(17) . ?
C6 O7 1.3205(17) . ?
O7 C7 1.4506(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.481(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O8 H8D 0.8698 . ?
O8 H8E 0.8700 . ?

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
C1 O1 H1 109.5 . . ?
O1 C1 C2 118.80(12) . . ?
O2 C1 O1 120.55(13) . . ?
O2 C1 C2 120.65(14) . . ?
C2 N2 N3 118.70(10) . . ?
C1 C2 C3 119.23(11) . . ?
N2 C2 C1 113.41(11) . . ?
N2 C2 C3 127.36(11) . . ?
N2 N3 H3 121.2 . . ?
N2 N3 C6 117.57(10) . . ?
C6 N3 H3 121.2 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C2 C3 C4 113.09(10) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C5 O4 H4 109.5 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.28(11) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
O3 C5 O4 123.77(12) . . ?
O3 C5 C4 124.40(12) . . ?
O4 C5 C4 111.84(11) . . ?
O6 C6 N3 125.01(13) . . ?
O6 C6 O7 126.38(12) . . ?
O7 C6 N3 108.59(11) . . ?
C6 O7 C7 116.88(12) . . ?
O7 C7 H7A 110.4 . . ?
O7 C7 H7B 110.4 . . ?
O7 C7 C8 106.55(14) . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H8D O8 H8E 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
