# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1945478'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;
_audit_creation_date             2019-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 Co N2 O4, 2(C8 H5 N2 O6)'
_chemical_formula_sum            'C30 H28 Co N6 O16'
_chemical_formula_weight         787.51
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   27.2275(6)
_cell_length_b                   16.8312(5)
_cell_length_c                   14.5288(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.280(2)
_cell_angle_gamma                90
_cell_volume                     6529.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    27896
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.10
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.508
_shelx_estimated_absorpt_T_min   0.441
_exptl_absorpt_coefficient_mu    4.903
_exptl_absorpt_correction_T_max  0.563
_exptl_absorpt_correction_T_min  0.024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35970
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.638
_diffrn_reflns_theta_min         3.104
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4910
_reflns_number_total             6181
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         6181
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.129
_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)+(0.0339P)²+13.7886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 C26-N5A \\sim C26-N5B \\sim C18-N3A \\sim C18-N3B
 with sigma of 0.005
 N5A-O13A \\sim N5B-O13B \\sim N5A-O14A \\sim N5B-O14B
 with sigma of 0.005
 N6-O15A \\sim N6-O15B \\sim N6-O16A \\sim N6-O16B
 with sigma of 0.005
 N3A-O9A \\sim N3A-O10A \\sim N3B-O9B \\sim N3B-O10B
 with sigma of 0.005
 O13A-O14A \\sim O13B-O14B \\sim O15A-O16A \\sim O15B-O16B
 with sigma of 0.01
 O9A-O10A \\sim O9B-O10B
 with sigma of 0.01
 C26-O13A \\sim C26-O13B \\sim C26-O14A \\sim C26-O14B
 with sigma of 0.01
 C28-O15A \\sim C28-O15B \\sim C28-O16A \\sim C28-O16B
 with sigma of 0.01
 C18-O9A \\sim C18-O10A \\sim C18-O9B \\sim C18-O10B
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O13A) = Uanis(O14A)
Uanis(O13B) = Uanis(O14B)
Uanis(O15B) = Uanis(O16B)
Uanis(O15A) = Uanis(O16A)
Uanis(N5A) = Uanis(N5B)
Uanis(N3A) = Uanis(N3B)
Uanis(O10A) = Uanis(O10B)
Uanis(O9A) = Uanis(O9B)
4. Rigid body (RIGU) restrains
 O9A, O10A, N3A, O13A, O14A, O15A, O16A, O9B, O10B, N3B, O13B, O14B, O15B,
 O16B, N5A, N5B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O13B)=Sof(O14B)=Sof(N5B)=1-FVAR(1)
 Sof(O13A)=Sof(O14A)=Sof(N5A)=FVAR(1)
 Sof(O15B)=Sof(O16B)=1-FVAR(2)
 Sof(O15A)=Sof(O16A)=FVAR(2)
 Sof(O9B)=Sof(O10B)=Sof(N3B)=1-FVAR(3)
 Sof(O9A)=Sof(O10A)=Sof(N3A)=FVAR(3)
 Fixed Sof: H30A(0.5) H30B(0.5) H30C(0.5) H30D(0.5) H30E(0.5) H30F(0.5)
6.a Riding coordinates:
 O1(H1), O2(H2), O3(H3), O4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C8(H8A,H8B), C14(H14A,H14B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C5(H5), C10(H10), C11(H11), C12(H12), C17(H17), C21(H21),
 C25(H25), C29(H29)
6.d Disordered Me refined with riding coordinates:
 C30(H30A,H30B,H30C,H30D,H30E,H30F)
6.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
Co1 Co 0.36632(2) 0.41394(2) 0.54790(3) 0.01960(11) Uani 1 1 d . . . . .
O1 O 0.37029(6) 0.53993(10) 0.55051(12) 0.0243(4) Uani 1 1 d . . . . .
H1 H 0.361200 0.560951 0.497484 0.036 Uiso 1 1 d R . . . .
O2 O 0.39673(6) 0.29780(10) 0.55632(12) 0.0237(4) Uani 1 1 d . . . . .
H2 H 0.394464 0.275239 0.504083 0.036 Uiso 1 1 d R . . . .
O3 O 0.33618(7) 0.39669(10) 0.66772(12) 0.0258(4) Uani 1 1 d . . . . .
H3 H 0.350980 0.368115 0.712003 0.039 Uiso 1 1 d R . . . .
O4 O 0.36535(6) 0.41445(10) 0.40001(12) 0.0228(4) Uani 1 1 d . . . . .
H4 H 0.382140 0.379400 0.378916 0.034 Uiso 1 1 d R . . . .
N1 N 0.44019(8) 0.43405(12) 0.60247(15) 0.0220(5) Uani 1 1 d . . . . .
N2 N 0.29321(8) 0.39078(12) 0.49193(15) 0.0224(5) Uani 1 1 d . . . . .
C1 C 0.41773(10) 0.57214(15) 0.59482(19) 0.0271(6) Uani 1 1 d . . . . .
H1A H 0.414902 0.595604 0.656046 0.033 Uiso 1 1 calc R . . . .
H1B H 0.427407 0.614930 0.555120 0.033 Uiso 1 1 calc R . . . .
C2 C 0.45765(10) 0.50871(16) 0.60983(18) 0.0247(6) Uani 1 1 d . . . . .
C3 C 0.50865(10) 0.52422(17) 0.63163(19) 0.0300(6) Uani 1 1 d . . . . .
H3A H 0.520765 0.577283 0.636621 0.036 Uiso 1 1 calc R . . . .
C4 C 0.54149(10) 0.46058(18) 0.64594(19) 0.0323(7) Uani 1 1 d . . . . .
H4A H 0.576586 0.469713 0.660592 0.039 Uiso 1 1 calc R . . . .
C5 C 0.52317(10) 0.38369(17) 0.63889(18) 0.0283(6) Uani 1 1 d . . . . .
H5 H 0.545345 0.339593 0.649289 0.034 Uiso 1 1 calc R . . . .
C6 C 0.47177(10) 0.37230(16) 0.61632(17) 0.0237(6) Uani 1 1 d . . . . .
C7 C 0.44687(10) 0.29186(15) 0.60820(19) 0.0260(6) Uani 1 1 d . . . . .
H7A H 0.466100 0.254542 0.576197 0.031 Uiso 1 1 calc R . . . .
H7B H 0.446558 0.270718 0.671670 0.031 Uiso 1 1 calc R . . . .
C8 C 0.28411(10) 0.37700(17) 0.6523(2) 0.0303(6) Uani 1 1 d . . . . .
H8A H 0.265780 0.419178 0.679026 0.036 Uiso 1 1 calc R . . . .
H8B H 0.279703 0.326588 0.684815 0.036 Uiso 1 1 calc R . . . .
C9 C 0.26272(9) 0.36838(15) 0.54957(19) 0.0247(6) Uani 1 1 d . . . . .
C10 C 0.21508(10) 0.33936(16) 0.5144(2) 0.0309(6) Uani 1 1 d . . . . .
H10 H 0.193399 0.324543 0.555418 0.037 Uiso 1 1 calc R . . . .
C11 C 0.19995(10) 0.33256(16) 0.4182(2) 0.0322(7) Uani 1 1 d . . . . .
H11 H 0.167741 0.311769 0.392485 0.039 Uiso 1 1 calc R . . . .
C12 C 0.23155(10) 0.35593(16) 0.3589(2) 0.0291(6) Uani 1 1 d . . . . .
H12 H 0.221262 0.351876 0.292685 0.035 Uiso 1 1 calc R . . . .
C13 C 0.27822(9) 0.38517(15) 0.39837(19) 0.0234(6) Uani 1 1 d . . . . .
C14 C 0.31602(9) 0.41583(16) 0.34347(18) 0.0255(6) Uani 1 1 d . . . . .
H14A H 0.315121 0.382479 0.287046 0.031 Uiso 1 1 calc R . . . .
H14B H 0.307261 0.470896 0.322504 0.031 Uiso 1 1 calc R . . . .
O5 O 0.34525(7) 0.60984(10) 0.39234(12) 0.0291(4) Uani 1 1 d . . . . .
O6 O 0.36730(7) 0.70313(11) 0.29926(13) 0.0278(4) Uani 1 1 d . . . . .
O11 O 0.27284(7) 0.69907(12) 0.65593(14) 0.0337(5) Uani 1 1 d . . . . .
O12 O 0.29699(8) 0.81200(13) 0.72148(14) 0.0391(5) Uani 1 1 d . . . . .
N4 N 0.29130(8) 0.76574(14) 0.65515(16) 0.0267(5) Uani 1 1 d . . . . .
C15 C 0.35248(9) 0.68058(15) 0.37168(18) 0.0234(6) Uani 1 1 d . . . . .
C16 C 0.34005(9) 0.74556(15) 0.43524(18) 0.0214(5) Uani 1 1 d . . . . .
C17 C 0.34170(9) 0.82402(15) 0.40742(19) 0.0242(6) Uani 1 1 d . . . . .
H17 H 0.353796 0.837282 0.352306 0.029 Uiso 1 1 calc R . . . .
C18 C 0.32562(9) 0.88248(14) 0.46060(18) 0.0248(6) Uani 1 1 d D . . . .
C19 C 0.30742(9) 0.86999(15) 0.54316(19) 0.0250(6) Uani 1 1 d . . . . .
C20 C 0.30829(9) 0.78985(15) 0.56896(18) 0.0224(5) Uani 1 1 d . . . . .
C21 C 0.32326(9) 0.72860(15) 0.51715(18) 0.0229(5) Uani 1 1 d . . . . .
H21 H 0.322032 0.675167 0.537656 0.027 Uiso 1 1 calc R . . . .
C22 C 0.28553(11) 0.93601(17) 0.5922(2) 0.0332(7) Uani 1 1 d . . . . .
H22A H 0.309826 0.952361 0.648007 0.050 Uiso 1 1 calc GR . . . .
H22B H 0.254865 0.917313 0.611080 0.050 Uiso 1 1 calc GR . . . .
H22C H 0.277636 0.981338 0.549569 0.050 Uiso 1 1 calc GR . . . .
O7 O 0.41075(7) 0.31069(11) 0.31655(14) 0.0320(5) Uani 1 1 d . . . . .
O8 O 0.39023(7) 0.21410(11) 0.40857(13) 0.0316(4) Uani 1 1 d . . . . .
O9A O 0.3114(2) 0.9732(3) 0.3376(4) 0.0445(11) Uani 0.555(8) 1 d D U P A 1
O10A O 0.3462(4) 1.0158(4) 0.4763(7) 0.043(2) Uani 0.555(8) 1 d D U P A 1
N3A N 0.3281(5) 0.9631(3) 0.4216(5) 0.0317(10) Uani 0.555(8) 1 d D U P A 1
O13A O 0.4822(2) 0.2361(3) 0.0518(4) 0.0421(11) Uani 0.465(5) 1 d D U P B 1
O14A O 0.45873(17) 0.1224(3) -0.0187(3) 0.0421(11) Uani 0.465(5) 1 d D U P B 1
O15A O 0.42439(16) -0.0608(2) 0.3366(2) 0.0430(10) Uani 0.507(4) 1 d D U P C 1
O16A O 0.39754(16) -0.0903(2) 0.1915(3) 0.0430(10) Uani 0.507(4) 1 d D U P C 1
O9B O 0.2917(3) 0.9801(4) 0.3556(5) 0.0445(11) Uani 0.445(8) 1 d D U P A 2
O10B O 0.3559(5) 1.0114(5) 0.4642(9) 0.043(2) Uani 0.445(8) 1 d D U P A 2
N3B N 0.3235(5) 0.9650(4) 0.4256(8) 0.0317(10) Uani 0.445(8) 1 d D U P A 2
O13B O 0.45800(16) 0.2414(2) 0.0233(3) 0.0360(9) Uani 0.535(5) 1 d D U P B 2
O14B O 0.50369(13) 0.1370(2) 0.0253(3) 0.0360(9) Uani 0.535(5) 1 d D U P B 2
O15B O 0.37273(13) -0.0575(2) 0.2544(3) 0.0397(10) Uani 0.493(4) 1 d D U P C 2
O16B O 0.44797(14) -0.0892(2) 0.2338(3) 0.0397(10) Uani 0.493(4) 1 d D U P C 2
N5A N 0.4653(3) 0.1685(3) 0.0478(4) 0.0320(8) Uani 0.465(5) 1 d D U P B 1
N5B N 0.4716(3) 0.1753(3) 0.0565(4) 0.0320(8) Uani 0.535(5) 1 d D U P B 2
N6 N 0.41578(9) -0.04179(14) 0.24911(17) 0.0377(6) Uani 1 1 d D . . . .
C23 C 0.40516(10) 0.23933(16) 0.33750(19) 0.0262(6) Uani 1 1 d . . . . .
C24 C 0.41776(9) 0.17703(15) 0.27098(18) 0.0240(6) Uani 1 1 d . . . . .
C25 C 0.43659(10) 0.19906(16) 0.19303(19) 0.0268(6) Uani 1 1 d . . . . .
H25 H 0.440881 0.253695 0.180220 0.032 Uiso 1 1 calc R . . . .
C26 C 0.44920(9) 0.14163(16) 0.13368(18) 0.0267(6) Uani 1 1 d D . . . .
C27 C 0.44432(10) 0.06003(17) 0.1472(2) 0.0296(6) Uani 1 1 d . . . . .
C28 C 0.42403(10) 0.04164(16) 0.2259(2) 0.0288(6) Uani 1 1 d D . . . .
C29 C 0.41093(10) 0.09703(16) 0.2876(2) 0.0271(6) Uani 1 1 d . . . . .
H29 H 0.397546 0.080494 0.340190 0.033 Uiso 1 1 calc R . . . .
C30 C 0.45992(14) -0.0028(2) 0.0854(3) 0.0523(10) Uani 1 1 d . . . . .
H30A H 0.452861 -0.055444 0.108691 0.078 Uiso 0.5 1 calc R . P . .
H30B H 0.441204 0.003906 0.021073 0.078 Uiso 0.5 1 calc R . P . .
H30C H 0.495867 0.001972 0.086227 0.078 Uiso 0.5 1 calc R . P . .
H30D H 0.473761 0.022400 0.035302 0.078 Uiso 0.5 1 calc R . P . .
H30E H 0.485417 -0.036950 0.122921 0.078 Uiso 0.5 1 calc R . P . .
H30F H 0.430755 -0.035016 0.057767 0.078 Uiso 0.5 1 calc R . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.1232(17) . ?
Co1 O2 2.1172(17) . ?
Co1 O3 2.0850(17) . ?
Co1 O4 2.1437(17) . ?
Co1 N1 2.041(2) . ?
Co1 N2 2.035(2) . ?
O1 C1 1.432(3) . ?
O2 C7 1.428(3) . ?
O3 C8 1.430(3) . ?
O4 C14 1.431(3) . ?
N1 C2 1.340(3) . ?
N1 C6 1.339(3) . ?
N2 C9 1.344(3) . ?
N2 C13 1.344(3) . ?
C1 C2 1.508(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.385(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.387(4) . ?
C6 C7 1.508(4) . ?
C8 C9 1.499(4) . ?
C9 C10 1.386(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.388(4) . ?
C12 C13 1.379(4) . ?
C13 C14 1.511(4) . ?
O5 C15 1.253(3) . ?
O6 C15 1.257(3) . ?
O11 N4 1.231(3) . ?
O12 N4 1.225(3) . ?
N4 C20 1.474(3) . ?
C15 C16 1.512(3) . ?
C16 C17 1.384(4) . ?
C16 C21 1.385(4) . ?
C17 C18 1.375(4) . ?
C18 C19 1.400(4) . ?
C18 N3A 1.477(4) . ?
C18 N3B 1.476(4) . ?
C19 C20 1.399(4) . ?
C19 C22 1.505(4) . ?
C20 C21 1.384(4) . ?
O7 C23 1.256(3) . ?
O8 C23 1.255(3) . ?
O9A N3A 1.228(4) . ?
O10A N3A 1.228(4) . ?
O13A N5A 1.224(4) . ?
O14A N5A 1.225(4) . ?
O15A N6 1.287(3) . ?
O16A N6 1.205(3) . ?
O9B N3B 1.227(4) . ?
O10B N3B 1.227(4) . ?
O13B N5B 1.240(3) . ?
O14B N5B 1.241(4) . ?
O15B N6 1.218(3) . ?
O16B N6 1.237(3) . ?
N5A C26 1.473(4) . ?
N5B C26 1.489(4) . ?
N6 C28 1.472(4) . ?
C23 C24 1.510(4) . ?
C24 C25 1.382(4) . ?
C24 C29 1.387(4) . ?
C25 C26 1.382(4) . ?
C26 C27 1.397(4) . ?
C27 C28 1.399(4) . ?
C27 C30 1.501(4) . ?
C28 C29 1.388(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
O1 Co1 O4 90.26(7) . . ?
O2 Co1 O1 154.57(7) . . ?
O2 Co1 O4 89.40(7) . . ?
O3 Co1 O1 98.69(7) . . ?
O3 Co1 O2 92.09(7) . . ?
O3 Co1 O4 155.20(7) . . ?
N1 Co1 O1 77.56(8) . . ?
N1 Co1 O2 77.65(8) . . ?
N1 Co1 O3 102.57(8) . . ?
N1 Co1 O4 101.93(7) . . ?
N2 Co1 O1 103.93(8) . . ?
N2 Co1 O2 100.79(7) . . ?
N2 Co1 O3 78.05(8) . . ?
N2 Co1 O4 77.35(7) . . ?
N2 Co1 N1 178.31(8) . . ?
C1 O1 Co1 115.11(14) . . ?
C7 O2 Co1 114.70(14) . . ?
C8 O3 Co1 116.18(15) . . ?
C14 O4 Co1 113.67(14) . . ?
C2 N1 Co1 119.59(18) . . ?
C6 N1 Co1 119.00(17) . . ?
C6 N1 C2 120.6(2) . . ?
C9 N2 Co1 118.69(18) . . ?
C9 N2 C13 120.6(2) . . ?
C13 N2 Co1 119.83(16) . . ?
O1 C1 C2 111.0(2) . . ?
N1 C2 C1 114.7(2) . . ?
N1 C2 C3 121.2(3) . . ?
C3 C2 C1 124.1(2) . . ?
C4 C3 C2 118.5(3) . . ?
C5 C4 C3 120.0(3) . . ?
C4 C5 C6 118.6(3) . . ?
N1 C6 C5 121.1(2) . . ?
N1 C6 C7 114.8(2) . . ?
C5 C6 C7 124.0(2) . . ?
O2 C7 C6 110.3(2) . . ?
O3 C8 C9 111.0(2) . . ?
N2 C9 C8 115.2(2) . . ?
N2 C9 C10 121.1(3) . . ?
C10 C9 C8 123.6(2) . . ?
C11 C10 C9 118.3(3) . . ?
C10 C11 C12 120.4(3) . . ?
C13 C12 C11 118.4(3) . . ?
N2 C13 C12 121.3(2) . . ?
N2 C13 C14 114.0(2) . . ?
C12 C13 C14 124.7(2) . . ?
O4 C14 C13 110.6(2) . . ?
O11 N4 C20 117.1(2) . . ?
O12 N4 O11 124.1(2) . . ?
O12 N4 C20 118.8(2) . . ?
O5 C15 O6 125.4(2) . . ?
O5 C15 C16 118.5(2) . . ?
O6 C15 C16 116.1(2) . . ?
C17 C16 C15 119.2(2) . . ?
C17 C16 C21 118.8(2) . . ?
C21 C16 C15 121.8(2) . . ?
C18 C17 C16 119.1(2) . . ?
C17 C18 C19 125.4(2) . . ?
C17 C18 N3A 113.4(5) . . ?
C17 C18 N3B 118.4(7) . . ?
C19 C18 N3A 121.2(5) . . ?
C19 C18 N3B 116.1(7) . . ?
C18 C19 C22 122.3(2) . . ?
C20 C19 C18 112.6(2) . . ?
C20 C19 C22 124.9(2) . . ?
C19 C20 N4 120.1(2) . . ?
C21 C20 N4 115.6(2) . . ?
C21 C20 C19 124.3(2) . . ?
C20 C21 C16 119.7(2) . . ?
O9A N3A C18 118.2(4) . . ?
O9A N3A O10A 124.5(4) . . ?
O10A N3A C18 117.3(4) . . ?
O9B N3B C18 117.0(4) . . ?
O9B N3B O10B 125.0(5) . . ?
O10B N3B C18 117.8(5) . . ?
O13A N5A O14A 128.5(4) . . ?
O13A N5A C26 114.6(4) . . ?
O14A N5A C26 116.8(4) . . ?
O13B N5B O14B 120.1(3) . . ?
O13B N5B C26 119.9(3) . . ?
O14B N5B C26 119.9(3) . . ?
O15A N6 C28 117.2(3) . . ?
O16A N6 O15A 119.2(3) . . ?
O16A N6 C28 123.2(3) . . ?
O15B N6 O16B 126.5(3) . . ?
O15B N6 C28 114.4(3) . . ?
O16B N6 C28 115.4(3) . . ?
O7 C23 C24 117.1(2) . . ?
O8 C23 O7 126.7(2) . . ?
O8 C23 C24 116.2(2) . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 C29 119.2(2) . . ?
C29 C24 C23 120.5(2) . . ?
C24 C25 C26 120.1(2) . . ?
C25 C26 N5A 117.7(3) . . ?
C25 C26 N5B 113.1(3) . . ?
C25 C26 C27 123.9(2) . . ?
C27 C26 N5A 118.2(3) . . ?
C27 C26 N5B 122.9(3) . . ?
C26 C27 C28 113.3(2) . . ?
C26 C27 C30 124.3(3) . . ?
C28 C27 C30 122.4(3) . . ?
C27 C28 N6 120.1(2) . . ?
C29 C28 N6 115.0(2) . . ?
C29 C28 C27 124.9(3) . . ?
C24 C29 C28 118.6(3) . . ?

_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_2
_database_code_depnum_ccdc_archive 'CCDC 1945479'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;
_audit_creation_date             2019-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 Co0.8 N2 O4 Zn0.2, 2(C8 H5 N2 O6)'
_chemical_formula_sum            'C30 H28 Co0.80 N6 O16 Zn0.20'
_chemical_formula_weight         788.78
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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                   27.2147(9)
_cell_length_b                   16.8283(7)
_cell_length_c                   14.5231(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.134(3)
_cell_angle_gamma                90
_cell_volume                     6526.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    25881
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.81
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.546
_shelx_estimated_absorpt_T_min   0.438
_exptl_absorpt_coefficient_mu    4.301
_exptl_absorpt_correction_T_max  0.172
_exptl_absorpt_correction_T_min  0.038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light pink'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3245
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33310
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.751
_diffrn_reflns_theta_min         3.104
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4597
_reflns_number_total             6225
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       'X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)'
_computing_data_reduction        
'X-Area Integrate 1.73.1.0 (STOE, 2018) X-Area LANA 1.73.2.0 (STOE, 2018)'
_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         1.051
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6225
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.091
_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)+(0.0732P)²+22.0487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1594
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Shared sites
{Co1, Zn1}
3. Restrained distances
 C26-N5A \\sim C26-N5B \\sim C18-N3A \\sim C18-N3B
 with sigma of 0.005
 N5A-O13A \\sim N5B-O13B \\sim N5A-O14A \\sim N5B-O14B
 with sigma of 0.005
 N6-O15A \\sim N6-O15B \\sim N6-O16A \\sim N6-O16B
 with sigma of 0.005
 N3A-O9A \\sim N3A-O10A \\sim N3B-O9B \\sim N3B-O10B
 with sigma of 0.005
 O13A-O14A \\sim O13B-O14B \\sim O15A-O16A \\sim O15B-O16B
 with sigma of 0.01
 O9A-O10A \\sim O9B-O10B
 with sigma of 0.01
 C26-O13A \\sim C26-O13B \\sim C26-O14A \\sim C26-O14B
 with sigma of 0.01
 C28-O15A \\sim C28-O15B \\sim C28-O16A \\sim C28-O16B
 with sigma of 0.01
 C18-O9A \\sim C18-O10A \\sim C18-O9B \\sim C18-O10B
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(O13A) = Uanis(O14A)
Uanis(O13B) = Uanis(O14B)
Uanis(O15B) = Uanis(O16B)
Uanis(O15A) = Uanis(O16A)
Uanis(N5A) = Uanis(N5B)
Uanis(N3A) = Uanis(N3B)
Uanis(O10A) = Uanis(O10B)
Uanis(O9A) = Uanis(O9B)
Uanis(Co1) = Uanis(Zn1)
5. Rigid body (RIGU) restrains
 O9A, O10A, N3A, O13A, O14A, O15A, O16A, O9B, O10B, N3B, O13B, O14B, O15B,
 O16B, N5A, N5B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(O13B)=Sof(O14B)=Sof(N5B)=1-FVAR(1)
 Sof(O13A)=Sof(O14A)=Sof(N5A)=FVAR(1)
 Sof(O15B)=Sof(O16B)=1-FVAR(2)
 Sof(O15A)=Sof(O16A)=FVAR(2)
 Sof(O9B)=Sof(O10B)=Sof(N3B)=1-FVAR(3)
 Sof(O9A)=Sof(O10A)=Sof(N3A)=FVAR(3)
 Sof(Zn1)=1-FVAR(4)
 Sof(Co1)=FVAR(4)
 Fixed Sof: H30A(0.5) H30B(0.5) H30C(0.5) H30D(0.5) H30E(0.5) H30F(0.5)
7.a Riding coordinates:
 O1(H1), O2(H2), O3(H3), O4(H4)
7.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C8(H8A,H8B), C14(H14A,H14B)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C5(H5), C10(H10), C11(H11), C12(H12), C17(H17), C21(H21),
 C25(H25), C29(H29)
7.d Disordered Me refined with riding coordinates:
 C30(H30A,H30B,H30C,H30D,H30E,H30F)
7.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
Co1 Co 0.36643(2) 0.41392(3) 0.54881(4) 0.0258(2) Uani 0.804(12) 1 d . . P A 1
Zn1 Zn 0.36643(2) 0.41392(3) 0.54881(4) 0.0258(2) Uani 0.196(12) 1 d . . P A 2
O1 O 0.37042(9) 0.54067(15) 0.55305(19) 0.0330(6) Uani 1 1 d . . . . .
H1 H 0.361343 0.561693 0.500009 0.049 Uiso 1 1 d R . . A .
O2 O 0.39666(9) 0.29668(15) 0.55834(19) 0.0331(6) Uani 1 1 d . . . . .
H2 H 0.394387 0.274124 0.506113 0.050 Uiso 1 1 d R . . A .
O3 O 0.33557(10) 0.39804(16) 0.6687(2) 0.0353(6) Uani 1 1 d . . . . .
H3 H 0.350373 0.369481 0.712928 0.053 Uiso 1 1 d R . . A .
O4 O 0.36582(9) 0.41538(14) 0.39995(19) 0.0313(6) Uani 1 1 d . . . . .
H4 H 0.382610 0.380327 0.378863 0.047 Uiso 1 1 d R . . A .
N1 N 0.44022(11) 0.43369(18) 0.6021(2) 0.0285(7) Uani 1 1 d . . . . .
N2 N 0.29355(11) 0.39052(18) 0.4922(2) 0.0297(7) Uani 1 1 d . . . . .
C1 C 0.41815(15) 0.5720(2) 0.5956(3) 0.0353(9) Uani 1 1 d . . . . .
H1A H 0.415888 0.596123 0.656791 0.042 Uiso 1 1 calc R . . . .
H1B H 0.427721 0.614339 0.555049 0.042 Uiso 1 1 calc R . . . .
C2 C 0.45783(14) 0.5086(2) 0.6102(3) 0.0327(9) Uani 1 1 d . . . . .
C3 C 0.50879(15) 0.5234(3) 0.6314(3) 0.0375(9) Uani 1 1 d . . . . .
H3A H 0.521059 0.576396 0.636171 0.045 Uiso 1 1 calc R . . . .
C4 C 0.54152(15) 0.4599(3) 0.6455(3) 0.0411(10) Uani 1 1 d . . . . .
H4A H 0.576638 0.468788 0.660058 0.049 Uiso 1 1 calc R . . . .
C5 C 0.52290(15) 0.3831(3) 0.6383(3) 0.0380(9) Uani 1 1 d . . . . .
H5 H 0.545022 0.338947 0.648442 0.046 Uiso 1 1 calc R . . . .
C6 C 0.47193(14) 0.3717(2) 0.6164(3) 0.0310(8) Uani 1 1 d . . . . .
C7 C 0.44684(14) 0.2914(2) 0.6084(3) 0.0329(9) Uani 1 1 d . . . . .
H7A H 0.465820 0.254215 0.575619 0.039 Uiso 1 1 calc R . . . .
H7B H 0.447072 0.270028 0.672013 0.039 Uiso 1 1 calc R . . . .
C8 C 0.28398(15) 0.3769(3) 0.6528(3) 0.0380(9) Uani 1 1 d . . . . .
H8A H 0.265017 0.418308 0.679452 0.046 Uiso 1 1 calc R . . . .
H8B H 0.280035 0.326128 0.685015 0.046 Uiso 1 1 calc R . . . .
C9 C 0.26302(14) 0.3682(2) 0.5494(3) 0.0323(9) Uani 1 1 d . . . . .
C10 C 0.21519(14) 0.3394(2) 0.5142(3) 0.0370(10) Uani 1 1 d . . . . .
H10 H 0.193369 0.324748 0.555052 0.044 Uiso 1 1 calc R . . . .
C11 C 0.20027(15) 0.3327(2) 0.4180(3) 0.0418(11) Uani 1 1 d . . . . .
H11 H 0.168110 0.311913 0.392128 0.050 Uiso 1 1 calc R . . . .
C12 C 0.23219(14) 0.3562(2) 0.3589(3) 0.0366(9) Uani 1 1 d . . . . .
H12 H 0.222126 0.352126 0.292734 0.044 Uiso 1 1 calc R . . . .
C13 C 0.27874(14) 0.3856(2) 0.3986(3) 0.0306(8) Uani 1 1 d . . . . .
C14 C 0.31636(14) 0.4159(2) 0.3436(3) 0.0331(9) Uani 1 1 d . . . . .
H14A H 0.315606 0.382143 0.287539 0.040 Uiso 1 1 calc R . . . .
H14B H 0.307409 0.470787 0.321961 0.040 Uiso 1 1 calc R . . . .
O5 O 0.34511(11) 0.60934(15) 0.3941(2) 0.0382(7) Uani 1 1 d . . . . .
O6 O 0.36729(10) 0.70191(15) 0.2999(2) 0.0354(6) Uani 1 1 d . . . . .
O11 O 0.27281(11) 0.70027(17) 0.6574(2) 0.0420(7) Uani 1 1 d . . . . .
O12 O 0.29720(12) 0.81322(19) 0.7220(2) 0.0484(8) Uani 1 1 d . . . . .
N4 N 0.29135(11) 0.7670(2) 0.6560(2) 0.0346(8) Uani 1 1 d . . . . .
C15 C 0.35226(14) 0.6800(2) 0.3721(3) 0.0311(8) Uani 1 1 d . . . . .
C16 C 0.34003(13) 0.7451(2) 0.4359(3) 0.0282(8) Uani 1 1 d . . . . .
C17 C 0.34172(13) 0.8240(2) 0.4075(3) 0.0305(8) Uani 1 1 d . . . . .
H17 H 0.354037 0.837164 0.352548 0.037 Uiso 1 1 calc R . . . .
C18 C 0.32522(13) 0.8825(2) 0.4605(3) 0.0322(9) Uani 1 1 d D . . . .
C19 C 0.30742(13) 0.8703(2) 0.5433(3) 0.0318(9) Uani 1 1 d . . . . .
C20 C 0.30826(13) 0.7906(2) 0.5695(3) 0.0298(8) Uani 1 1 d . . . . .
C21 C 0.32303(13) 0.7286(2) 0.5181(3) 0.0306(8) Uani 1 1 d . . . . .
H21 H 0.321539 0.675249 0.538864 0.037 Uiso 1 1 calc R . . . .
C22 C 0.28552(16) 0.9367(2) 0.5918(3) 0.0400(10) Uani 1 1 d . . . . .
H22A H 0.309870 0.953569 0.647157 0.060 Uiso 1 1 calc GR . . . .
H22B H 0.254943 0.918141 0.611221 0.060 Uiso 1 1 calc GR . . . .
H22C H 0.277490 0.981651 0.548611 0.060 Uiso 1 1 calc GR . . . .
O7 O 0.41164(11) 0.31095(16) 0.3179(2) 0.0402(7) Uani 1 1 d . . . . .
O8 O 0.39006(11) 0.21455(17) 0.4089(2) 0.0408(7) Uani 1 1 d . . . . .
O9A O 0.3119(3) 0.9728(4) 0.3375(5) 0.0498(16) Uani 0.557(11) 1 d D U P B 1
O10A O 0.3469(8) 1.0154(5) 0.4760(10) 0.052(4) Uani 0.557(11) 1 d D U P B 1
N3A N 0.3281(7) 0.9631(4) 0.4216(7) 0.0395(13) Uani 0.557(11) 1 d D U P B 1
O13A O 0.4826(3) 0.2367(4) 0.0500(5) 0.0518(17) Uani 0.455(7) 1 d D U P C 1
O14A O 0.4587(3) 0.1229(4) -0.0190(4) 0.0518(17) Uani 0.455(7) 1 d D U P C 1
O15A O 0.4242(2) -0.0599(3) 0.3358(3) 0.0528(16) Uani 0.510(6) 1 d D U P D 1
O16A O 0.3960(2) -0.0888(3) 0.1906(4) 0.0528(16) Uani 0.510(6) 1 d D U P D 1
O9B O 0.2909(4) 0.9788(6) 0.3532(7) 0.0498(16) Uani 0.443(11) 1 d D U P B 2
O10B O 0.3549(11) 1.0115(7) 0.4610(14) 0.052(4) Uani 0.443(11) 1 d D U P B 2
N3B N 0.3231(8) 0.9642(5) 0.4227(11) 0.0395(13) Uani 0.443(11) 1 d D U P B 2
O13B O 0.4574(2) 0.2412(3) 0.0239(5) 0.0466(14) Uani 0.545(7) 1 d D U P C 2
O14B O 0.50333(19) 0.1367(3) 0.0258(4) 0.0466(14) Uani 0.545(7) 1 d D U P C 2
O15B O 0.37265(17) -0.0588(3) 0.2549(5) 0.0470(16) Uani 0.490(6) 1 d D U P D 2
O16B O 0.4483(2) -0.0888(3) 0.2353(5) 0.0470(16) Uani 0.490(6) 1 d D U P D 2
N5A N 0.4653(4) 0.1690(4) 0.0481(5) 0.0413(11) Uani 0.455(7) 1 d D U P C 1
N5B N 0.4711(3) 0.1751(3) 0.0566(5) 0.0413(11) Uani 0.545(7) 1 d D U P C 2
N6 N 0.41576(12) -0.0414(2) 0.2498(2) 0.0445(9) Uani 1 1 d D . . . .
C23 C 0.40534(14) 0.2396(2) 0.3387(3) 0.0352(9) Uani 1 1 d . . . . .
C24 C 0.41786(14) 0.1773(2) 0.2714(3) 0.0327(9) Uani 1 1 d . . . . .
C25 C 0.43661(14) 0.1991(2) 0.1933(3) 0.0355(9) Uani 1 1 d . . . . .
H25 H 0.440915 0.253761 0.180322 0.043 Uiso 1 1 calc R . . . .
C26 C 0.44904(14) 0.1420(2) 0.1341(3) 0.0355(9) Uani 1 1 d D . . . .
C27 C 0.44413(14) 0.0600(2) 0.1475(3) 0.0368(9) Uani 1 1 d . . . . .
C28 C 0.42397(14) 0.0421(2) 0.2261(3) 0.0360(9) Uani 1 1 d D . . . .
C29 C 0.41105(14) 0.0971(2) 0.2880(3) 0.0346(9) Uani 1 1 d . . . . .
H29 H 0.397791 0.080415 0.340736 0.041 Uiso 1 1 calc R . . . .
C30 C 0.4596(2) -0.0024(3) 0.0854(4) 0.0600(14) Uani 1 1 d . . . . .
H30A H 0.472755 0.023043 0.034517 0.090 Uiso 0.5 1 calc R . P . .
H30B H 0.485655 -0.035992 0.122253 0.090 Uiso 0.5 1 calc R . P . .
H30C H 0.430588 -0.035264 0.058843 0.090 Uiso 0.5 1 calc R . P . .
H30D H 0.453244 -0.055185 0.109225 0.090 Uiso 0.5 1 calc R . P . .
H30E H 0.440344 0.003850 0.021489 0.090 Uiso 0.5 1 calc R . P . .
H30F H 0.495411 0.003122 0.084899 0.090 Uiso 0.5 1 calc R . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.136(3) . ?
Co1 O2 2.132(3) . ?
Co1 O3 2.091(3) . ?
Co1 O4 2.159(3) . ?
Co1 N1 2.035(3) . ?
Co1 N2 2.033(3) . ?
Zn1 O1 2.136(3) . ?
Zn1 O2 2.132(3) . ?
Zn1 O3 2.091(3) . ?
Zn1 O4 2.159(3) . ?
Zn1 N1 2.035(3) . ?
Zn1 N2 2.033(3) . ?
O1 C1 1.427(5) . ?
O2 C7 1.421(4) . ?
O3 C8 1.423(5) . ?
O4 C14 1.434(4) . ?
N1 C2 1.345(5) . ?
N1 C6 1.344(5) . ?
N2 C9 1.337(5) . ?
N2 C13 1.345(5) . ?
C1 C2 1.504(6) . ?
C2 C3 1.384(5) . ?
C3 C4 1.382(6) . ?
C4 C5 1.384(6) . ?
C5 C6 1.376(5) . ?
C6 C7 1.508(5) . ?
C8 C9 1.506(6) . ?
C9 C10 1.391(5) . ?
C10 C11 1.382(6) . ?
C11 C12 1.391(6) . ?
C12 C13 1.378(5) . ?
C13 C14 1.504(6) . ?
O5 C15 1.257(5) . ?
O6 C15 1.252(5) . ?
O11 N4 1.233(4) . ?
O12 N4 1.221(4) . ?
N4 C20 1.473(5) . ?
C15 C16 1.513(5) . ?
C16 C17 1.393(5) . ?
C16 C21 1.389(6) . ?
C17 C18 1.378(5) . ?
C18 C19 1.395(6) . ?
C18 N3A 1.478(5) . ?
C18 N3B 1.478(5) . ?
C19 C20 1.394(5) . ?
C19 C22 1.504(5) . ?
C20 C21 1.387(5) . ?
O7 C23 1.259(5) . ?
O8 C23 1.247(5) . ?
O9A N3A 1.227(5) . ?
O10A N3A 1.227(5) . ?
O13A N5A 1.230(4) . ?
O14A N5A 1.231(4) . ?
O15A N6 1.265(4) . ?
O16A N6 1.220(4) . ?
O9B N3B 1.227(5) . ?
O10B N3B 1.227(5) . ?
O13B N5B 1.239(4) . ?
O14B N5B 1.239(4) . ?
O15B N6 1.225(4) . ?
O16B N6 1.240(4) . ?
N5A C26 1.475(5) . ?
N5B C26 1.483(5) . ?
N6 C28 1.473(5) . ?
C23 C24 1.515(6) . ?
C24 C25 1.381(6) . ?
C24 C29 1.391(5) . ?
C25 C26 1.374(5) . ?
C26 C27 1.403(6) . ?
C27 C28 1.392(6) . ?
C27 C30 1.498(6) . ?
C28 C29 1.382(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O4 90.46(10) . . ?
O2 Co1 O1 154.89(10) . . ?
O2 Co1 O4 90.22(10) . . ?
O3 Co1 O1 97.47(10) . . ?
O3 Co1 O2 92.27(11) . . ?
O3 Co1 O4 155.30(10) . . ?
N1 Co1 O1 77.58(11) . . ?
N1 Co1 O2 77.68(11) . . ?
N1 Co1 O3 103.28(12) . . ?
N1 Co1 O4 101.26(11) . . ?
N2 Co1 O1 104.20(11) . . ?
N2 Co1 O2 100.43(11) . . ?
N2 Co1 O3 78.12(12) . . ?
N2 Co1 O4 77.25(12) . . ?
N2 Co1 N1 177.64(13) . . ?
O1 Zn1 O4 90.46(10) . . ?
O2 Zn1 O1 154.89(10) . . ?
O2 Zn1 O4 90.22(10) . . ?
O3 Zn1 O1 97.47(10) . . ?
O3 Zn1 O2 92.27(11) . . ?
O3 Zn1 O4 155.30(10) . . ?
N1 Zn1 O1 77.58(11) . . ?
N1 Zn1 O2 77.68(11) . . ?
N1 Zn1 O3 103.28(12) . . ?
N1 Zn1 O4 101.26(11) . . ?
N2 Zn1 O1 104.20(11) . . ?
N2 Zn1 O2 100.43(11) . . ?
N2 Zn1 O3 78.12(12) . . ?
N2 Zn1 O4 77.25(12) . . ?
N2 Zn1 N1 177.64(13) . . ?
C1 O1 Co1 114.7(2) . . ?
C1 O1 Zn1 114.7(2) . . ?
C7 O2 Co1 114.3(2) . . ?
C7 O2 Zn1 114.3(2) . . ?
C8 O3 Co1 116.0(2) . . ?
C8 O3 Zn1 116.0(2) . . ?
C14 O4 Co1 113.4(2) . . ?
C14 O4 Zn1 113.4(2) . . ?
C2 N1 Co1 119.7(3) . . ?
C2 N1 Zn1 119.7(3) . . ?
C6 N1 Co1 119.2(2) . . ?
C6 N1 Zn1 119.2(2) . . ?
C6 N1 C2 120.4(3) . . ?
C9 N2 Co1 118.6(3) . . ?
C9 N2 Zn1 118.6(3) . . ?
C9 N2 C13 120.7(3) . . ?
C13 N2 Co1 119.9(2) . . ?
C13 N2 Zn1 119.9(2) . . ?
O1 C1 C2 111.5(3) . . ?
N1 C2 C1 114.8(3) . . ?
N1 C2 C3 120.9(4) . . ?
C3 C2 C1 124.4(4) . . ?
C4 C3 C2 118.9(4) . . ?
C3 C4 C5 119.7(4) . . ?
C6 C5 C4 119.1(4) . . ?
N1 C6 C5 121.0(4) . . ?
N1 C6 C7 114.6(3) . . ?
C5 C6 C7 124.4(4) . . ?
O2 C7 C6 111.1(3) . . ?
O3 C8 C9 111.0(3) . . ?
N2 C9 C8 115.5(3) . . ?
N2 C9 C10 121.2(4) . . ?
C10 C9 C8 123.3(4) . . ?
C11 C10 C9 118.2(4) . . ?
C10 C11 C12 120.2(4) . . ?
C13 C12 C11 118.5(4) . . ?
N2 C13 C12 121.1(4) . . ?
N2 C13 C14 114.5(3) . . ?
C12 C13 C14 124.4(4) . . ?
O4 C14 C13 110.8(3) . . ?
O11 N4 C20 117.1(3) . . ?
O12 N4 O11 124.0(4) . . ?
O12 N4 C20 118.9(3) . . ?
O5 C15 C16 117.8(4) . . ?
O6 C15 O5 125.6(4) . . ?
O6 C15 C16 116.5(3) . . ?
C17 C16 C15 119.0(3) . . ?
C21 C16 C15 122.0(3) . . ?
C21 C16 C17 118.8(4) . . ?
C18 C17 C16 118.8(4) . . ?
C17 C18 C19 125.5(3) . . ?
C17 C18 N3A 113.3(7) . . ?
C17 C18 N3B 116.8(11) . . ?
C19 C18 N3A 121.2(7) . . ?
C19 C18 N3B 117.5(11) . . ?
C18 C19 C22 121.9(3) . . ?
C20 C19 C18 112.8(3) . . ?
C20 C19 C22 125.0(4) . . ?
C19 C20 N4 120.1(3) . . ?
C21 C20 N4 115.3(3) . . ?
C21 C20 C19 124.6(4) . . ?
C20 C21 C16 119.4(4) . . ?
O9A N3A C18 117.9(4) . . ?
O10A N3A C18 117.3(5) . . ?
O10A N3A O9A 124.8(5) . . ?
O9B N3B C18 117.6(5) . . ?
O9B N3B O10B 124.9(6) . . ?
O10B N3B C18 117.5(5) . . ?
O13A N5A O14A 126.7(6) . . ?
O13A N5A C26 116.2(5) . . ?
O14A N5A C26 117.0(4) . . ?
O13B N5B O14B 120.8(5) . . ?
O13B N5B C26 119.4(4) . . ?
O14B N5B C26 119.8(4) . . ?
O15A N6 C28 117.3(4) . . ?
O16A N6 O15A 120.4(5) . . ?
O16A N6 C28 121.7(4) . . ?
O15B N6 O16B 125.4(5) . . ?
O15B N6 C28 115.6(4) . . ?
O16B N6 C28 115.4(4) . . ?
O7 C23 C24 116.5(4) . . ?
O8 C23 O7 127.0(4) . . ?
O8 C23 C24 116.5(4) . . ?
C25 C24 C23 120.8(4) . . ?
C25 C24 C29 118.9(4) . . ?
C29 C24 C23 120.4(4) . . ?
C26 C25 C24 120.2(4) . . ?
C25 C26 N5A 117.6(4) . . ?
C25 C26 N5B 113.4(4) . . ?
C25 C26 C27 124.0(4) . . ?
C27 C26 N5A 118.2(4) . . ?
C27 C26 N5B 122.5(4) . . ?
C26 C27 C30 124.1(4) . . ?
C28 C27 C26 113.0(4) . . ?
C28 C27 C30 122.9(4) . . ?
C27 C28 N6 120.0(3) . . ?
C29 C28 N6 114.7(4) . . ?
C29 C28 C27 125.3(4) . . ?
C28 C29 C24 118.6(4) . . ?

_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_3
_database_code_depnum_ccdc_archive 'CCDC 1945480'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;
_audit_creation_date             2019-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 N2 O4 Zn, 2(C8 H5 N2 O6)'
_chemical_formula_sum            'C30 H28 N6 O16 Zn'
_chemical_formula_weight         793.95
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   27.3034(9)
_cell_length_b                   16.8405(8)
_cell_length_c                   14.4655(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.163(3)
_cell_angle_gamma                90
_cell_volume                     6525.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    27215
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.76
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.838
_shelx_estimated_absorpt_T_min   0.784
_exptl_absorpt_coefficient_mu    1.828
_exptl_absorpt_correction_T_max  0.657
_exptl_absorpt_correction_T_min  0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3264
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            35121
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.909
_diffrn_reflns_theta_min         3.100
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4682
_reflns_number_total             6207
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.000190(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6207
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      1.078
_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)+(0.0359P)²+79.4458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 C26-N5A \\sim C26-N5B \\sim C18-N3A \\sim C18-N3B
 with sigma of 0.005
 N5A-O13A \\sim N5B-O13B \\sim N5A-O14A \\sim N5B-O14B
 with sigma of 0.005
 N6-O15A \\sim N6-O15B \\sim N6-O16A \\sim N6-O16B
 with sigma of 0.005
 N3A-O9A \\sim N3A-O10A \\sim N3B-O9B \\sim N3B-O10B
 with sigma of 0.005
 O13A-O14A \\sim O13B-O14B \\sim O15A-O16A \\sim O15B-O16B
 with sigma of 0.01
 O9A-O10A \\sim O9B-O10B
 with sigma of 0.01
 C26-O13A \\sim C26-O13B \\sim C26-O14A \\sim C26-O14B
 with sigma of 0.01
 C28-O15A \\sim C28-O15B \\sim C28-O16A \\sim C28-O16B
 with sigma of 0.01
 C18-O9A \\sim C18-O10A \\sim C18-O9B \\sim C18-O10B
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O13A) = Uanis(O14A)
Uanis(O13B) = Uanis(O14B)
Uanis(O15B) = Uanis(O16B)
Uanis(O15A) = Uanis(O16A)
Uanis(N5A) = Uanis(N5B)
Uanis(N3A) = Uanis(N3B)
Uanis(O10A) = Uanis(O10B)
Uanis(O9A) = Uanis(O9B)
4. Rigid body (RIGU) restrains
 O9A, O10A, N3A, O13A, O14A, O15A, O16A, O9B, O10B, N3B, O13B, O14B, O15B,
 O16B, N5A, N5B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O13B)=Sof(O14B)=Sof(N5B)=1-FVAR(1)
 Sof(O13A)=Sof(O14A)=Sof(N5A)=FVAR(1)
 Sof(O15B)=Sof(O16B)=1-FVAR(2)
 Sof(O15A)=Sof(O16A)=FVAR(2)
 Sof(O9B)=Sof(O10B)=Sof(N3B)=1-FVAR(3)
 Sof(O9A)=Sof(O10A)=Sof(N3A)=FVAR(3)
 Fixed Sof: H30A(0.5) H30B(0.5) H30C(0.5) H30D(0.5) H30E(0.5) H30F(0.5)
6.a Riding coordinates:
 O1(H1), O2(H2), O3(H3), O4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C8(H8A,H8B), C14(H14A,H14B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C5(H5), C10(H10), C11(H11), C12(H12), C17(H17), C21(H21),
 C25(H25), C29(H29)
6.d Disordered Me refined with riding coordinates:
 C30(H30A,H30B,H30C,H30D,H30E,H30F)
6.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
Zn1 Zn 0.36657(2) 0.41397(4) 0.55051(5) 0.0265(2) Uani 1 1 d . . . . .
O1 O 0.37052(13) 0.5418(2) 0.5579(3) 0.0311(8) Uani 1 1 d . . . . .
H1 H 0.361427 0.562831 0.504838 0.047 Uiso 1 1 d R . . . .
O2 O 0.39643(13) 0.29460(19) 0.5623(3) 0.0300(8) Uani 1 1 d . . . . .
H2 H 0.394163 0.272039 0.510049 0.045 Uiso 1 1 d R . . . .
O3 O 0.33448(13) 0.4011(2) 0.6708(2) 0.0304(8) Uani 1 1 d . . . . .
H3 H 0.349263 0.372589 0.715052 0.046 Uiso 1 1 d R . . . .
O4 O 0.36658(12) 0.4169(2) 0.3997(2) 0.0280(7) Uani 1 1 d . . . . .
H4 H 0.383374 0.381881 0.378592 0.042 Uiso 1 1 d R . . . .
N1 N 0.44046(15) 0.4331(2) 0.6023(3) 0.0276(9) Uani 1 1 d . . . . .
N2 N 0.29424(15) 0.3901(2) 0.4930(3) 0.0275(9) Uani 1 1 d . . . . .
C1 C 0.4192(2) 0.5723(3) 0.5982(4) 0.0336(12) Uani 1 1 d . . . . .
H1A H 0.418326 0.596698 0.660117 0.040 Uiso 1 1 calc R . . . .
H1B H 0.428461 0.614136 0.556603 0.040 Uiso 1 1 calc R . . . .
C2 C 0.45831(19) 0.5073(3) 0.6108(4) 0.0294(11) Uani 1 1 d . . . . .
C3 C 0.5089(2) 0.5226(3) 0.6310(4) 0.0339(12) Uani 1 1 d . . . . .
H3A H 0.521152 0.575466 0.635987 0.041 Uiso 1 1 calc R . . . .
C4 C 0.5413(2) 0.4582(4) 0.6439(4) 0.0379(13) Uani 1 1 d . . . . .
H4A H 0.576303 0.466917 0.656837 0.046 Uiso 1 1 calc R . . . .
C5 C 0.5228(2) 0.3817(3) 0.6381(4) 0.0364(12) Uani 1 1 d . . . . .
H5 H 0.544816 0.337576 0.649033 0.044 Uiso 1 1 calc R . . . .
C6 C 0.47164(19) 0.3705(3) 0.6159(3) 0.0289(11) Uani 1 1 d . . . . .
C7 C 0.44734(19) 0.2899(3) 0.6090(4) 0.0324(12) Uani 1 1 d . . . . .
H7A H 0.465601 0.253515 0.573972 0.039 Uiso 1 1 calc R . . . .
H7B H 0.449169 0.268014 0.673120 0.039 Uiso 1 1 calc R . . . .
C8 C 0.28322(19) 0.3762(3) 0.6532(4) 0.0347(12) Uani 1 1 d . . . . .
H8A H 0.263006 0.415628 0.680167 0.042 Uiso 1 1 calc R . . . .
H8B H 0.280467 0.324635 0.684599 0.042 Uiso 1 1 calc R . . . .
C9 C 0.26337(19) 0.3681(3) 0.5499(4) 0.0302(11) Uani 1 1 d . . . . .
C10 C 0.21546(19) 0.3396(3) 0.5137(4) 0.0344(12) Uani 1 1 d . . . . .
H10 H 0.193471 0.325022 0.554329 0.041 Uiso 1 1 calc R . . . .
C11 C 0.2012(2) 0.3334(3) 0.4178(4) 0.0360(13) Uani 1 1 d . . . . .
H11 H 0.169056 0.313043 0.391420 0.043 Uiso 1 1 calc R . . . .
C12 C 0.2332(2) 0.3567(3) 0.3582(4) 0.0336(12) Uani 1 1 d . . . . .
H12 H 0.223258 0.353121 0.291689 0.040 Uiso 1 1 calc R . . . .
C13 C 0.27982(19) 0.3849(3) 0.3990(4) 0.0301(11) Uani 1 1 d . . . . .
C14 C 0.31781(18) 0.4159(3) 0.3435(4) 0.0315(11) Uani 1 1 d . . . . .
H14A H 0.317535 0.381614 0.287760 0.038 Uiso 1 1 calc R . . . .
H14B H 0.308405 0.470262 0.320852 0.038 Uiso 1 1 calc R . . . .
O5 O 0.34504(14) 0.6083(2) 0.3971(3) 0.0354(9) Uani 1 1 d . . . . .
O6 O 0.36725(13) 0.6999(2) 0.3007(3) 0.0329(8) Uani 1 1 d . . . . .
O11 O 0.27253(14) 0.7024(2) 0.6599(3) 0.0399(9) Uani 1 1 d . . . . .
O12 O 0.29811(16) 0.8154(3) 0.7231(3) 0.0454(10) Uani 1 1 d . . . . .
N4 N 0.29159(16) 0.7687(3) 0.6570(3) 0.0331(10) Uani 1 1 d . . . . .
C15 C 0.35209(18) 0.6788(3) 0.3740(4) 0.0306(11) Uani 1 1 d . . . . .
C16 C 0.33972(18) 0.7454(3) 0.4366(3) 0.0262(10) Uani 1 1 d . . . . .
C17 C 0.34143(18) 0.8228(3) 0.4071(4) 0.0296(11) Uani 1 1 d . . . . .
H17 H 0.353663 0.835151 0.351619 0.036 Uiso 1 1 calc R . . . .
C18 C 0.32520(18) 0.8821(3) 0.4591(3) 0.0286(11) Uani 1 1 d D . . . .
C19 C 0.30748(18) 0.8708(3) 0.5426(4) 0.0300(11) Uani 1 1 d . . . . .
C20 C 0.30840(18) 0.7916(3) 0.5701(4) 0.0286(11) Uani 1 1 d . . . . .
C21 C 0.32332(18) 0.7294(3) 0.5190(4) 0.0280(11) Uani 1 1 d . . . . .
H21 H 0.322247 0.676260 0.540672 0.034 Uiso 1 1 calc R . . . .
C22 C 0.2858(2) 0.9378(3) 0.5919(4) 0.0393(13) Uani 1 1 d . . . . .
H22A H 0.311286 0.958035 0.643651 0.059 Uiso 1 1 calc GR . . . .
H22B H 0.257237 0.917969 0.617109 0.059 Uiso 1 1 calc GR . . . .
H22C H 0.274709 0.980618 0.546857 0.059 Uiso 1 1 calc GR . . . .
O7 O 0.41303(14) 0.3112(2) 0.3207(3) 0.0383(9) Uani 1 1 d . . . . .
O8 O 0.38944(15) 0.2152(2) 0.4107(3) 0.0390(9) Uani 1 1 d . . . . .
O9A O 0.3119(5) 0.9732(5) 0.3365(6) 0.0487(19) Uani 0.559(13) 1 d D U P A 1
O10A O 0.3477(11) 1.0149(6) 0.4751(12) 0.048(4) Uani 0.559(13) 1 d D U P A 1
N3A N 0.3291(8) 0.9626(4) 0.4204(7) 0.035(2) Uani 0.559(13) 1 d D U P A 1
O13A O 0.4812(4) 0.2381(5) 0.0484(6) 0.050(2) Uani 0.463(9) 1 d D U P B 1
O14A O 0.4584(3) 0.1247(5) -0.0198(5) 0.050(2) Uani 0.463(9) 1 d D U P B 1
O15A O 0.4241(3) -0.0593(4) 0.3370(4) 0.052(2) Uani 0.518(8) 1 d D U P C 1
O16A O 0.3942(3) -0.0867(4) 0.1916(5) 0.052(2) Uani 0.518(8) 1 d D U P C 1
O9B O 0.2893(5) 0.9756(7) 0.3493(8) 0.0487(19) Uani 0.441(13) 1 d D U P A 2
O10B O 0.3524(14) 1.0124(9) 0.4563(17) 0.048(4) Uani 0.441(13) 1 d D U P A 2
N3B N 0.3211(10) 0.9635(6) 0.4202(13) 0.035(2) Uani 0.441(13) 1 d D U P A 2
O13B O 0.4574(3) 0.2413(4) 0.0247(6) 0.0410(17) Uani 0.537(9) 1 d D U P B 2
O14B O 0.5033(3) 0.1368(4) 0.0271(5) 0.0410(17) Uani 0.537(9) 1 d D U P B 2
O15B O 0.3728(2) -0.0602(4) 0.2554(6) 0.044(2) Uani 0.482(8) 1 d D U P C 2
O16B O 0.4480(3) -0.0885(4) 0.2362(6) 0.044(2) Uani 0.482(8) 1 d D U P C 2
N5A N 0.4659(5) 0.1695(4) 0.0487(6) 0.0399(13) Uani 0.463(9) 1 d D U P B 1
N5B N 0.4711(4) 0.1754(4) 0.0567(7) 0.0399(13) Uani 0.537(9) 1 d D U P B 2
N6 N 0.41586(16) -0.0407(3) 0.2516(3) 0.0446(12) Uani 1 1 d D . . . .
C23 C 0.40576(19) 0.2403(3) 0.3402(4) 0.0321(12) Uani 1 1 d . . . . .
C24 C 0.41833(19) 0.1782(3) 0.2736(4) 0.0303(11) Uani 1 1 d . . . . .
C25 C 0.43661(19) 0.1995(3) 0.1949(4) 0.0328(12) Uani 1 1 d . . . . .
H25 H 0.440761 0.254122 0.181918 0.039 Uiso 1 1 calc R . . . .
C26 C 0.44904(19) 0.1426(3) 0.1346(3) 0.0331(12) Uani 1 1 d D . . . .
C27 C 0.4443(2) 0.0607(3) 0.1487(4) 0.0348(12) Uani 1 1 d . . . . .
C28 C 0.42346(19) 0.0424(3) 0.2271(4) 0.0348(12) Uani 1 1 d D . . . .
C29 C 0.41108(19) 0.0977(3) 0.2897(4) 0.0335(12) Uani 1 1 d . . . . .
H29 H 0.397876 0.081113 0.342644 0.040 Uiso 1 1 calc R . . . .
C30 C 0.4591(3) -0.0029(4) 0.0856(5) 0.0552(18) Uani 1 1 d . . . . .
H30A H 0.472873 0.021988 0.035049 0.083 Uiso 0.5 1 calc R . P . .
H30B H 0.484233 -0.037677 0.122699 0.083 Uiso 0.5 1 calc R . P . .
H30C H 0.429581 -0.034290 0.058214 0.083 Uiso 0.5 1 calc R . P . .
H30D H 0.451585 -0.055307 0.108925 0.083 Uiso 0.5 1 calc R . P . .
H30E H 0.440225 0.004357 0.021276 0.083 Uiso 0.5 1 calc R . P . .
H30F H 0.494877 0.000971 0.085761 0.083 Uiso 0.5 1 calc R . 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
Zn1 O1 2.157(3) . ?
Zn1 O2 2.164(3) . ?
Zn1 O3 2.105(3) . ?
Zn1 O4 2.182(3) . ?
Zn1 N1 2.037(4) . ?
Zn1 N2 2.029(4) . ?
O1 C1 1.440(6) . ?
O2 C7 1.425(6) . ?
O3 C8 1.436(6) . ?
O4 C14 1.420(6) . ?
N1 C2 1.339(6) . ?
N1 C6 1.346(6) . ?
N2 C9 1.339(6) . ?
N2 C13 1.343(7) . ?
C1 C2 1.515(7) . ?
C2 C3 1.378(7) . ?
C3 C4 1.388(8) . ?
C4 C5 1.380(8) . ?
C5 C6 1.385(7) . ?
C6 C7 1.505(7) . ?
C8 C9 1.494(8) . ?
C9 C10 1.396(7) . ?
C10 C11 1.371(8) . ?
C11 C12 1.398(8) . ?
C12 C13 1.379(7) . ?
C13 C14 1.522(7) . ?
O5 C15 1.257(6) . ?
O6 C15 1.263(6) . ?
O11 N4 1.236(6) . ?
O12 N4 1.225(6) . ?
N4 C20 1.470(6) . ?
C15 C16 1.520(7) . ?
C16 C17 1.376(7) . ?
C16 C21 1.379(7) . ?
C17 C18 1.373(7) . ?
C18 C19 1.399(7) . ?
C18 N3A 1.479(6) . ?
C18 N3B 1.479(6) . ?
C19 C20 1.390(7) . ?
C19 C22 1.515(7) . ?
C20 C21 1.388(7) . ?
O7 C23 1.253(6) . ?
O8 C23 1.262(6) . ?
O9A N3A 1.227(6) . ?
O10A N3A 1.227(6) . ?
O13A N5A 1.229(5) . ?
O14A N5A 1.229(5) . ?
O15A N6 1.253(5) . ?
O16A N6 1.226(5) . ?
O9B N3B 1.227(6) . ?
O10B N3B 1.227(6) . ?
O13B N5B 1.233(5) . ?
O14B N5B 1.234(5) . ?
O15B N6 1.232(5) . ?
O16B N6 1.242(5) . ?
N5A C26 1.477(6) . ?
N5B C26 1.482(6) . ?
N6 C28 1.468(7) . ?
C23 C24 1.506(7) . ?
C24 C25 1.375(7) . ?
C24 C29 1.396(7) . ?
C25 C26 1.382(7) . ?
C26 C27 1.404(7) . ?
C27 C28 1.399(8) . ?
C27 C30 1.512(7) . ?
C28 C29 1.385(7) . ?

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 Zn1 O2 155.36(14) . . ?
O1 Zn1 O4 90.97(13) . . ?
O2 Zn1 O4 91.55(13) . . ?
O3 Zn1 O1 94.96(13) . . ?
O3 Zn1 O2 92.89(13) . . ?
O3 Zn1 O4 155.40(13) . . ?
N1 Zn1 O1 77.74(15) . . ?
N1 Zn1 O2 77.69(15) . . ?
N1 Zn1 O3 104.68(15) . . ?
N1 Zn1 O4 99.92(14) . . ?
N2 Zn1 O1 104.68(15) . . ?
N2 Zn1 O2 99.80(15) . . ?
N2 Zn1 O3 77.91(15) . . ?
N2 Zn1 O4 77.49(14) . . ?
N2 Zn1 N1 176.40(17) . . ?
C1 O1 Zn1 114.2(3) . . ?
C7 O2 Zn1 114.0(3) . . ?
C8 O3 Zn1 115.5(3) . . ?
C14 O4 Zn1 113.0(3) . . ?
C2 N1 Zn1 119.9(3) . . ?
C2 N1 C6 120.6(4) . . ?
C6 N1 Zn1 118.9(3) . . ?
C9 N2 Zn1 118.8(4) . . ?
C9 N2 C13 120.5(4) . . ?
C13 N2 Zn1 119.9(3) . . ?
O1 C1 C2 111.4(4) . . ?
N1 C2 C1 115.4(4) . . ?
N1 C2 C3 121.7(5) . . ?
C3 C2 C1 123.0(5) . . ?
C2 C3 C4 118.0(5) . . ?
C5 C4 C3 120.3(5) . . ?
C4 C5 C6 118.8(5) . . ?
N1 C6 C5 120.5(5) . . ?
N1 C6 C7 116.0(4) . . ?
C5 C6 C7 123.4(5) . . ?
O2 C7 C6 111.0(4) . . ?
O3 C8 C9 110.9(4) . . ?
N2 C9 C8 116.1(4) . . ?
N2 C9 C10 121.4(5) . . ?
C10 C9 C8 122.6(5) . . ?
C11 C10 C9 117.9(5) . . ?
C10 C11 C12 120.9(5) . . ?
C13 C12 C11 117.9(5) . . ?
N2 C13 C12 121.4(5) . . ?
N2 C13 C14 114.6(4) . . ?
C12 C13 C14 124.0(5) . . ?
O4 C14 C13 111.2(4) . . ?
O11 N4 C20 118.0(4) . . ?
O12 N4 O11 123.5(4) . . ?
O12 N4 C20 118.5(5) . . ?
O5 C15 O6 125.6(5) . . ?
O5 C15 C16 118.4(5) . . ?
O6 C15 C16 116.0(4) . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 C21 119.3(5) . . ?
C21 C16 C15 121.2(4) . . ?
C18 C17 C16 119.0(5) . . ?
C17 C18 C19 125.2(4) . . ?
C17 C18 N3A 113.9(9) . . ?
C17 C18 N3B 118.3(13) . . ?
C19 C18 N3A 120.9(9) . . ?
C19 C18 N3B 116.2(13) . . ?
C18 C19 C22 122.5(5) . . ?
C20 C19 C18 112.8(4) . . ?
C20 C19 C22 124.5(5) . . ?
C19 C20 N4 120.3(4) . . ?
C21 C20 N4 115.4(4) . . ?
C21 C20 C19 124.2(5) . . ?
C16 C21 C20 119.4(5) . . ?
O9A N3A C18 117.8(5) . . ?
O10A N3A C18 117.8(5) . . ?
O10A N3A O9A 124.4(6) . . ?
O9B N3B C18 117.4(6) . . ?
O10B N3B C18 117.7(6) . . ?
O10B N3B O9B 124.6(7) . . ?
O13A N5A O14A 125.3(7) . . ?
O13A N5A C26 116.8(5) . . ?
O14A N5A C26 117.3(5) . . ?
O13B N5B O14B 121.8(6) . . ?
O13B N5B C26 118.8(5) . . ?
O14B N5B C26 119.3(5) . . ?
O15A N6 C28 118.0(4) . . ?
O16A N6 O15A 120.7(6) . . ?
O16A N6 C28 120.2(5) . . ?
O15B N6 O16B 123.3(6) . . ?
O15B N6 C28 116.4(4) . . ?
O16B N6 C28 115.9(4) . . ?
O7 C23 O8 126.7(5) . . ?
O7 C23 C24 116.9(5) . . ?
O8 C23 C24 116.4(5) . . ?
C25 C24 C23 120.8(5) . . ?
C25 C24 C29 118.5(5) . . ?
C29 C24 C23 120.7(5) . . ?
C24 C25 C26 121.0(5) . . ?
C25 C26 N5A 118.3(5) . . ?
C25 C26 N5B 114.1(5) . . ?
C25 C26 C27 123.2(5) . . ?
C27 C26 N5A 118.4(5) . . ?
C27 C26 N5B 122.6(5) . . ?
C26 C27 C30 124.5(5) . . ?
C28 C27 C26 113.5(5) . . ?
C28 C27 C30 122.1(5) . . ?
C27 C28 N6 120.3(4) . . ?
C29 C28 N6 114.8(4) . . ?
C29 C28 C27 124.8(5) . . ?
C28 C29 C24 118.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
