# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2008988'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H12 Br2 O4'
_chemical_formula_sum            'C12 H12 Br2 O4'
_chemical_formula_weight         380.04
_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'
Br Br -0.2901 2.4595 '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                   10.0468(3)
_cell_length_b                   7.6582(2)
_cell_length_c                   9.6509(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.188(3)
_cell_angle_gamma                90
_cell_volume                     660.50(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14777
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      32.2690
_cell_measurement_theta_min      3.4800
_shelx_estimated_absorpt_T_max   0.480
_shelx_estimated_absorpt_T_min   0.133
_exptl_absorpt_coefficient_mu    6.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   32.3860
_exptl_transmission_factor_min   3.5036
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            48241
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.025
_diffrn_reflns_theta_min         3.504
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2030
_reflns_number_total             2280
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.539
_refine_diff_density_min         -1.094
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         2280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.117
_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)+(0.0334P)²+0.9271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0794
_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
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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
O2 O 0.60392(17) -0.0736(2) 0.31224(19) 0.0253(3) Uani 1 1 d . . . . .
O1 O 0.6764(2) -0.1564(3) 0.1339(2) 0.0333(4) Uani 1 1 d . . . . .
C3 C 0.8575(2) -0.0441(3) 0.3811(2) 0.0178(3) Uani 1 1 d . . . . .
C1 C 1.1067(2) 0.0687(3) 0.4621(2) 0.0193(4) Uani 1 1 d . . . . .
H1 H 1.1793 0.1162 0.4354 0.023 Uiso 1 1 calc R . . . .
C4 C 0.7047(2) -0.0978(3) 0.2600(2) 0.0198(4) Uani 1 1 d . . . . .
C2 C 0.9661(2) 0.0244(3) 0.3452(2) 0.0184(3) Uani 1 1 d . . . . .
C5 C 0.4501(2) -0.1217(4) 0.2057(3) 0.0280(4) Uani 1 1 d . . . . .
H5A H 0.4471 -0.2380 0.1596 0.034 Uiso 1 1 calc R . . . .
H5B H 0.4055 -0.0352 0.1204 0.034 Uiso 1 1 calc R . . . .
C6 C 0.3653(3) -0.1248(4) 0.2998(3) 0.0342(5) Uani 1 1 d . . . . .
H6A H 0.4098 -0.2119 0.3829 0.051 Uiso 1 1 calc GR . . . .
H6B H 0.2606 -0.1552 0.2320 0.051 Uiso 1 1 calc GR . . . .
H6C H 0.3703 -0.0094 0.3458 0.051 Uiso 1 1 calc GR . . . .
Br1 Br 0.93289(3) 0.06466(3) 0.13843(2) 0.02899(8) 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
O2 C4 1.335(3) . ?
O2 C5 1.459(3) . ?
O1 C4 1.202(3) . ?
C3 C1 1.398(3) 3_756 ?
C3 C4 1.501(3) . ?
C3 C2 1.391(3) . ?
C1 C3 1.398(3) 3_756 ?
C1 C2 1.388(3) . ?
C2 Br1 1.8916(19) . ?
C5 C6 1.502(3) . ?

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
C4 O2 C5 116.17(17) . . ?
C1 C3 C4 118.18(18) 3_756 . ?
C2 C3 C1 118.50(17) . 3_756 ?
C2 C3 C4 123.30(18) . . ?
C2 C1 C3 120.69(18) . 3_756 ?
O2 C4 C3 110.48(17) . . ?
O1 C4 O2 124.37(19) . . ?
O1 C4 C3 125.15(19) . . ?
C3 C2 Br1 122.98(14) . . ?
C1 C2 C3 120.81(18) . . ?
C1 C2 Br1 116.21(15) . . ?
O2 C5 C6 106.78(19) . . ?

_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_ZnL(H2O)
_database_code_depnum_ccdc_archive 'CCDC 2008991'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H10 N2 O5 Zn'
_chemical_formula_sum            'C18 H10 N2 O5 Zn'
_chemical_formula_weight         399.65
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.620(2)
_cell_length_b                   8.4200(17)
_cell_length_c                   17.350(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.64(3)
_cell_angle_gamma                90
_cell_volume                     1478.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    33771
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.103
_cell_measurement_theta_min      2.016
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    1.698
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   27.103
_exptl_transmission_factor_min   2.016
_diffrn_reflns_av_R_equivalents  0.1459
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33771
_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         27.103
_diffrn_reflns_theta_min         2.016
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Dectris Eiger 9M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_source                   Synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2277
_reflns_number_total             3265
_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       'XDS (Kabsch, 1993)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_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         1.691
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.013
_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)+(0.0639P)²+4.0959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1394
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_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
C1 C 0.9680(4) 0.5792(6) 0.6068(3) 0.0250(10) Uani 1 1 d . . . . .
H1 H 0.9953 0.5133 0.6534 0.030 Uiso 1 1 calc R . . . .
C2 C 0.8347(4) 0.5852(6) 0.5637(3) 0.0248(10) Uani 1 1 d . . . . .
H2 H 0.7726 0.5263 0.5816 0.030 Uiso 1 1 calc R . . . .
C3 C 0.7920(4) 0.6779(6) 0.4939(3) 0.0210(9) Uani 1 1 d . . . . .
C4 C 0.8876(4) 0.7622(6) 0.4717(3) 0.0241(10) Uani 1 1 d . . . . .
H4 H 0.8634 0.8271 0.4247 0.029 Uiso 1 1 calc R . . . .
C5 C 1.0182(5) 0.7513(6) 0.5183(3) 0.0249(10) Uani 1 1 d . . . . .
H5 H 1.0821 0.8100 0.5019 0.030 Uiso 1 1 calc R . . . .
C6 C 0.6493(4) 0.6965(6) 0.4498(3) 0.0213(9) Uani 1 1 d . . . . .
C7 C 0.5607(4) 0.7154(6) 0.4948(3) 0.0223(10) Uani 1 1 d . . . . .
H7 H 0.5925 0.7036 0.5519 0.027 Uiso 1 1 calc R . . . .
C8 C 0.4274(4) 0.7510(6) 0.4587(3) 0.0222(10) Uani 1 1 d . . . . .
C9 C 0.3775(4) 0.7583(6) 0.3736(3) 0.0209(10) Uani 1 1 d . . . . .
C10 C 0.4651(4) 0.7376(6) 0.3287(3) 0.0223(10) Uani 1 1 d . . . . .
H10 H 0.4325 0.7435 0.2714 0.027 Uiso 1 1 calc R . . . .
C11 C 0.5989(4) 0.7088(5) 0.3652(3) 0.0203(10) Uani 1 1 d . . . . .
C12 C 0.2343(4) 0.7798(6) 0.3281(3) 0.0231(10) Uani 1 1 d . . . . .
C13 C 0.1516(4) 0.8917(7) 0.3477(3) 0.0262(11) Uani 1 1 d . . . . .
H13 H 0.1853 0.9616 0.3922 0.031 Uiso 1 1 calc R . . . .
C14 C 0.0185(4) 0.8998(7) 0.3010(3) 0.0270(11) Uani 1 1 d . . . . .
H14 H -0.0360 0.9770 0.3150 0.032 Uiso 1 1 calc R . . . .
C15 C 0.0448(5) 0.6969(6) 0.2192(3) 0.0275(11) Uani 1 1 d . . . . .
H15 H 0.0091 0.6290 0.1741 0.033 Uiso 1 1 calc R . . . .
C16 C 0.1766(4) 0.6808(6) 0.2625(3) 0.0264(10) Uani 1 1 d . . . . .
H16 H 0.2285 0.6017 0.2474 0.032 Uiso 1 1 calc R . . . .
C17 C 0.3506(4) 0.7863(6) 0.5169(3) 0.0222(10) Uani 1 1 d . . . . .
C18 C 0.6844(4) 0.6857(6) 0.3103(2) 0.0211(9) Uani 1 1 d . . . . .
N1 N 1.0600(3) 0.6620(5) 0.5856(2) 0.0230(9) Uani 1 1 d . . . . .
N2 N -0.0362(4) 0.8043(5) 0.2377(2) 0.0226(8) Uani 1 1 d . . . . .
O1 O 0.3334(3) 0.6736(4) 0.56095(18) 0.0239(7) Uani 1 1 d . . . . .
O2 O 0.3162(3) 0.9279(5) 0.5197(2) 0.0310(8) Uani 1 1 d . . . . .
O3 O 0.7482(3) 0.5611(4) 0.31388(18) 0.0213(7) Uani 1 1 d . . . . .
O4 O 0.6824(3) 0.7998(4) 0.26182(18) 0.0220(7) Uani 1 1 d . . . . .
O5 O 0.7585(3) 0.0712(4) 0.35255(18) 0.0249(7) Uani 1 1 d . . . . .
Zn1 Zn 0.74053(5) 0.31929(7) 0.33813(3) 0.02004(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.387(6) . ?
C1 N1 1.338(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(6) . ?
C3 C4 1.385(6) . ?
C3 C6 1.484(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(6) . ?
C5 H5 0.9500 . ?
C5 N1 1.347(6) . ?
C6 C7 1.403(6) . ?
C6 C11 1.405(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.396(6) . ?
C8 C9 1.411(6) . ?
C8 C17 1.508(6) . ?
C9 C10 1.393(6) . ?
C9 C12 1.498(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(6) . ?
C11 C18 1.514(6) . ?
C12 C13 1.398(7) . ?
C12 C16 1.394(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.401(6) . ?
C14 H14 0.9500 . ?
C14 N2 1.343(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(7) . ?
C15 N2 1.352(6) . ?
C16 H16 0.9500 . ?
C17 O1 1.266(6) . ?
C17 O2 1.253(6) . ?
C18 O3 1.240(6) . ?
C18 O4 1.273(6) . ?
N1 Zn1 2.137(4) 3_766 ?
N2 Zn1 2.174(4) 2 ?
O1 Zn1 2.125(3) 3_666 ?
O3 Zn1 2.086(3) . ?
O4 Zn1 2.136(3) 2_655 ?
O5 Zn1 2.105(4) . ?
Zn1 N1 2.137(4) 3_766 ?
Zn1 N2 2.174(4) 2_545 ?
Zn1 O1 2.125(3) 3_666 ?
Zn1 O4 2.136(3) 2_645 ?

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
C2 C1 H1 118.5 . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 122.9(4) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.9(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C6 121.3(4) . . ?
C4 C3 C2 117.0(4) . . ?
C4 C3 C6 121.5(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 118.2 . . ?
N1 C5 C4 123.6(5) . . ?
N1 C5 H5 118.2 . . ?
C7 C6 C3 118.5(4) . . ?
C7 C6 C11 117.8(4) . . ?
C11 C6 C3 123.5(4) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.3(4) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C9 119.2(4) . . ?
C7 C8 C17 115.0(4) . . ?
C9 C8 C17 125.8(4) . . ?
C8 C9 C12 123.8(4) . . ?
C10 C9 C8 118.5(4) . . ?
C10 C9 C12 117.7(4) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.0(4) . . ?
C11 C10 H10 119.0 . . ?
C6 C11 C18 122.4(4) . . ?
C10 C11 C6 120.2(4) . . ?
C10 C11 C18 117.4(4) . . ?
C13 C12 C9 124.5(4) . . ?
C16 C12 C9 118.9(4) . . ?
C16 C12 C13 116.7(4) . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.3(5) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 118.2 . . ?
N2 C14 C13 123.7(5) . . ?
N2 C14 H14 118.2 . . ?
C16 C15 H15 118.4 . . ?
N2 C15 H15 118.4 . . ?
N2 C15 C16 123.3(5) . . ?
C12 C16 H16 119.7 . . ?
C15 C16 C12 120.5(5) . . ?
C15 C16 H16 119.7 . . ?
O1 C17 C8 117.6(4) . . ?
O2 C17 C8 115.9(4) . . ?
O2 C17 O1 126.4(4) . . ?
O3 C18 C11 120.0(4) . . ?
O3 C18 O4 124.8(4) . . ?
O4 C18 C11 115.2(4) . . ?
C1 N1 C5 116.9(4) . . ?
C1 N1 Zn1 122.5(3) . 3_766 ?
C5 N1 Zn1 120.0(3) . 3_766 ?
C14 N2 C15 116.5(4) . . ?
C14 N2 Zn1 124.4(3) . 2 ?
C15 N2 Zn1 119.0(3) . 2 ?
C17 O1 Zn1 129.3(3) . 3_666 ?
C18 O3 Zn1 141.4(3) . . ?
C18 O4 Zn1 131.4(3) . 2_655 ?
N1 Zn1 N2 178.67(16) 3_766 2_545 ?
O1 Zn1 N1 91.85(13) 3_666 3_766 ?
O1 Zn1 N2 87.15(13) 3_666 2_545 ?
O1 Zn1 O4 177.09(13) 3_666 2_645 ?
O3 Zn1 N1 87.76(14) . 3_766 ?
O3 Zn1 N2 91.56(14) . 2_545 ?
O3 Zn1 O1 100.68(13) . 3_666 ?
O3 Zn1 O4 82.14(12) . 2_645 ?
O3 Zn1 O5 169.99(12) . . ?
O4 Zn1 N1 87.49(13) 2_645 3_766 ?
O4 Zn1 N2 93.55(13) 2_645 2_545 ?
O5 Zn1 N1 87.85(14) . 3_766 ?
O5 Zn1 N2 93.00(14) . 2_545 ?
O5 Zn1 O1 88.45(13) . 3_666 ?
O5 Zn1 O4 88.68(12) . 2_645 ?

_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_Et2L
_database_code_depnum_ccdc_archive 'CCDC 2008989'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H20 N2 O4'
_chemical_formula_sum            'C22 H20 N2 O4'
_chemical_formula_weight         376.40
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.4240(19)
_cell_length_b                   9.5020(19)
_cell_length_c                   20.940(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1875.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31317
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.889
_cell_measurement_theta_min      2.354
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  27.889
_exptl_absorpt_correction_T_min  2.354
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   27.889
_exptl_transmission_factor_min   2.354
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31317
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.889
_diffrn_reflns_theta_min         2.354
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Dectris Eiger 9M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_source                   Synchrotron
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4321
_reflns_number_total             4443
_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       'XDS (Kabsch, 1993)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_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         0.355
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1830 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_coef       0.156(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.117
_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)+(0.0493P)²+0.7238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1128
_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
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C16(H16), C2(H2), C11(H11), C4(H4), C13(H13), C1(H1), C15(H15),
 C14(H14), C5(H5)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C19(H19A,H19B,H19C)
;
_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
O4 O 0.63106(18) 0.39733(19) 0.65378(7) 0.0287(4) Uani 1 1 d . . . . .
O2 O 0.40669(18) 0.61777(19) 0.34467(7) 0.0282(4) Uani 1 1 d . . . . .
O1 O 0.5880(2) 0.4694(2) 0.32550(8) 0.0385(5) Uani 1 1 d . . . . .
O3 O 0.4575(2) 0.5547(2) 0.67311(8) 0.0389(5) Uani 1 1 d . . . . .
N1 N 0.5192(2) 1.0627(2) 0.39194(9) 0.0296(4) Uani 1 1 d . . . . .
N2 N 0.5261(2) -0.0430(2) 0.60522(9) 0.0295(4) Uani 1 1 d . . . . .
C12 C 0.5301(2) 0.2306(2) 0.55380(10) 0.0226(4) Uani 1 1 d . . . . .
C8 C 0.5333(2) 0.3925(2) 0.46035(10) 0.0231(4) Uani 1 1 d . . . . .
H8 H 0.5425 0.3124 0.4335 0.028 Uiso 1 1 calc R . . . .
C7 C 0.5229(2) 0.5259(2) 0.43333(10) 0.0220(4) Uani 1 1 d . . . . .
C9 C 0.5303(2) 0.3751(2) 0.52663(10) 0.0227(4) Uani 1 1 d . . . . .
C3 C 0.5128(2) 0.7903(2) 0.44428(10) 0.0231(4) Uani 1 1 d . . . . .
C6 C 0.5120(2) 0.6459(2) 0.47179(10) 0.0218(4) Uani 1 1 d . . . . .
C20 C 0.5293(2) 0.4869(2) 0.63688(10) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.4175(3) 0.1837(3) 0.59160(10) 0.0260(5) Uani 1 1 d . . . . .
H16 H 0.3397 0.2441 0.6006 0.031 Uiso 1 1 calc R . . . .
C2 C 0.4040(2) 0.8857(2) 0.45605(11) 0.0256(5) Uani 1 1 d . . . . .
H2 H 0.3260 0.8602 0.4823 0.031 Uiso 1 1 calc R . . . .
C11 C 0.5091(2) 0.6288(2) 0.53806(10) 0.0234(4) Uani 1 1 d . . . . .
H11 H 0.5001 0.7090 0.5648 0.028 Uiso 1 1 calc R . . . .
C10 C 0.5194(2) 0.4957(2) 0.56522(10) 0.0231(4) Uani 1 1 d . . . . .
C4 C 0.6257(2) 0.8354(2) 0.40645(10) 0.0247(4) Uani 1 1 d . . . . .
H4 H 0.7030 0.7741 0.3977 0.030 Uiso 1 1 calc R . . . .
C17 C 0.5123(2) 0.5337(2) 0.36169(10) 0.0253(4) Uani 1 1 d . . . . .
C13 C 0.6396(2) 0.1353(2) 0.54156(11) 0.0253(4) Uani 1 1 d . . . . .
H13 H 0.7174 0.1614 0.5152 0.030 Uiso 1 1 calc R . . . .
C1 C 0.4111(3) 1.0185(3) 0.42897(11) 0.0285(5) Uani 1 1 d . . . . .
H1 H 0.3353 1.0820 0.4369 0.034 Uiso 1 1 calc R . . . .
C15 C 0.4206(3) 0.0483(3) 0.61573(10) 0.0288(5) Uani 1 1 d . . . . .
H15 H 0.3432 0.0184 0.6414 0.035 Uiso 1 1 calc R . . . .
C14 C 0.6330(3) 0.0026(3) 0.56832(11) 0.0275(5) Uani 1 1 d . . . . .
H14 H 0.7090 -0.0605 0.5601 0.033 Uiso 1 1 calc R . . . .
C5 C 0.6239(3) 0.9707(3) 0.38171(11) 0.0290(5) Uani 1 1 d . . . . .
H5 H 0.7016 0.9997 0.3560 0.035 Uiso 1 1 calc R . . . .
C18 C 0.3836(3) 0.6390(3) 0.27665(11) 0.0400(6) Uani 1 1 d . . . . .
H18A H 0.3682 0.5475 0.2551 0.048 Uiso 1 1 calc R . . . .
H18B H 0.4671 0.6852 0.2571 0.048 Uiso 1 1 calc R . . . .
C21 C 0.6517(3) 0.3675(3) 0.72152(11) 0.0356(6) Uani 1 1 d . . . . .
H21A H 0.5592 0.3545 0.7431 0.043 Uiso 1 1 calc R . . . .
H21B H 0.7031 0.4456 0.7425 0.043 Uiso 1 1 calc R . . . .
C22 C 0.7369(3) 0.2351(3) 0.72429(14) 0.0427(7) Uani 1 1 d . . . . .
H22A H 0.8269 0.2490 0.7017 0.064 Uiso 1 1 calc GR . . . .
H22B H 0.6837 0.1586 0.7040 0.064 Uiso 1 1 calc GR . . . .
H22C H 0.7559 0.2109 0.7690 0.064 Uiso 1 1 calc GR . . . .
C19 C 0.2570(4) 0.7290(4) 0.26979(16) 0.0549(9) Uani 1 1 d . . . . .
H19A H 0.2343 0.7401 0.2244 0.082 Uiso 1 1 calc GR . . . .
H19B H 0.2760 0.8215 0.2886 0.082 Uiso 1 1 calc GR . . . .
H19C H 0.1766 0.6851 0.2918 0.082 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
O4 C20 1.330(3) . ?
O4 C21 1.460(3) . ?
O2 C17 1.325(3) . ?
O2 C18 1.455(3) . ?
O1 C17 1.207(3) . ?
O3 C20 1.204(3) . ?
N1 C1 1.348(3) . ?
N1 C5 1.336(3) . ?
N2 C15 1.338(3) . ?
N2 C14 1.342(3) . ?
C12 C9 1.487(3) . ?
C12 C16 1.397(3) . ?
C12 C13 1.396(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.391(3) . ?
C8 C9 1.398(3) . ?
C7 C6 1.400(3) . ?
C7 C17 1.505(3) . ?
C9 C10 1.406(3) . ?
C3 C6 1.488(3) . ?
C3 C2 1.391(3) . ?
C3 C4 1.394(3) . ?
C6 C11 1.397(3) . ?
C20 C10 1.506(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.382(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C1 H1 0.9500 . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?
C5 H5 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.475(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.493(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C20 O4 C21 118.61(19) . . ?
C17 O2 C18 117.35(19) . . ?
C5 N1 C1 116.5(2) . . ?
C15 N2 C14 116.3(2) . . ?
C16 C12 C9 120.8(2) . . ?
C13 C12 C9 121.8(2) . . ?
C13 C12 C16 117.3(2) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C7 C6 120.88(18) . . ?
C8 C7 C17 117.04(19) . . ?
C6 C7 C17 121.90(19) . . ?
C8 C9 C12 119.27(19) . . ?
C8 C9 C10 118.43(19) . . ?
C10 C9 C12 122.19(19) . . ?
C2 C3 C6 121.9(2) . . ?
C2 C3 C4 117.6(2) . . ?
C4 C3 C6 120.5(2) . . ?
C7 C6 C3 121.86(18) . . ?
C11 C6 C7 118.53(19) . . ?
C11 C6 C3 119.48(19) . . ?
O4 C20 C10 110.19(19) . . ?
O3 C20 O4 125.5(2) . . ?
O3 C20 C10 124.3(2) . . ?
C12 C16 H16 120.4 . . ?
C15 C16 C12 119.2(2) . . ?
C15 C16 H16 120.4 . . ?
C3 C2 H2 120.4 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.4 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
C9 C10 C20 121.6(2) . . ?
C11 C10 C9 120.74(19) . . ?
C11 C10 C20 117.6(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
O2 C17 C7 110.35(19) . . ?
O1 C17 O2 125.5(2) . . ?
O1 C17 C7 124.2(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.5 . . ?
N1 C1 C2 123.8(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
N2 C15 C16 124.0(2) . . ?
N2 C15 H15 118.0 . . ?
C16 C15 H15 118.0 . . ?
N2 C14 C13 124.2(2) . . ?
N2 C14 H14 117.9 . . ?
C13 C14 H14 117.9 . . ?
N1 C5 C4 123.8(2) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
O2 C18 H18A 110.3 . . ?
O2 C18 H18B 110.3 . . ?
O2 C18 C19 107.3(2) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
O4 C21 H21A 110.6 . . ?
O4 C21 H21B 110.6 . . ?
O4 C21 C22 105.8(2) . . ?
H21A C21 H21B 108.7 . . ?
C22 C21 H21A 110.6 . . ?
C22 C21 H21B 110.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
O4 C20 C10 C9 41.2(3) . . . . ?
O4 C20 C10 C11 -134.3(2) . . . . ?
O3 C20 C10 C9 -140.7(3) . . . . ?
O3 C20 C10 C11 43.7(3) . . . . ?
C12 C9 C10 C20 9.5(3) . . . . ?
C12 C9 C10 C11 -175.1(2) . . . . ?
C12 C16 C15 N2 0.0(3) . . . . ?
C12 C13 C14 N2 1.0(3) . . . . ?
C8 C7 C6 C3 174.8(2) . . . . ?
C8 C7 C6 C11 -1.1(3) . . . . ?
C8 C7 C17 O2 131.5(2) . . . . ?
C8 C7 C17 O1 -47.0(3) . . . . ?
C8 C9 C10 C20 -174.2(2) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C7 C8 C9 C12 175.2(2) . . . . ?
C7 C8 C9 C10 -1.2(3) . . . . ?
C7 C6 C11 C10 1.1(3) . . . . ?
C9 C12 C16 C15 179.6(2) . . . . ?
C9 C12 C13 C14 180.0(2) . . . . ?
C9 C8 C7 C6 1.2(3) . . . . ?
C9 C8 C7 C17 -174.0(2) . . . . ?
C3 C6 C11 C10 -175.0(2) . . . . ?
C3 C2 C1 N1 -0.9(3) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C6 C7 C17 O2 -43.7(3) . . . . ?
C6 C7 C17 O1 137.8(3) . . . . ?
C6 C3 C2 C1 -180.0(2) . . . . ?
C6 C3 C4 C5 -179.7(2) . . . . ?
C6 C11 C10 C9 -1.1(3) . . . . ?
C6 C11 C10 C20 174.4(2) . . . . ?
C20 O4 C21 C22 162.7(2) . . . . ?
C16 C12 C9 C8 -119.1(2) . . . . ?
C16 C12 C9 C10 57.1(3) . . . . ?
C16 C12 C13 C14 -1.5(3) . . . . ?
C2 C3 C6 C7 124.5(2) . . . . ?
C2 C3 C6 C11 -59.6(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C4 C3 C6 C7 -56.8(3) . . . . ?
C4 C3 C6 C11 119.1(2) . . . . ?
C4 C3 C2 C1 1.3(3) . . . . ?
C17 O2 C18 C19 176.9(2) . . . . ?
C17 C7 C6 C3 -10.1(3) . . . . ?
C17 C7 C6 C11 173.9(2) . . . . ?
C13 C12 C9 C8 59.3(3) . . . . ?
C13 C12 C9 C10 -124.5(2) . . . . ?
C13 C12 C16 C15 1.1(3) . . . . ?
C1 N1 C5 C4 0.4(3) . . . . ?
C15 N2 C14 C13 0.1(3) . . . . ?
C14 N2 C15 C16 -0.6(3) . . . . ?
C5 N1 C1 C2 0.0(3) . . . . ?
C18 O2 C17 O1 -2.6(4) . . . . ?
C18 O2 C17 C7 178.9(2) . . . . ?
C21 O4 C20 O3 5.7(4) . . . . ?
C21 O4 C20 C10 -176.3(2) . . . . ?

_olex2_diffrn_ambient_temperature_device ?
_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_Na2(H2L)L
_database_code_depnum_ccdc_archive 'CCDC 2008990'
loop_
_audit_author_name
_audit_author_address
'Jack Clegg'
;The University of Queensalnd
Australia
;
_audit_update_record             
;
2020-06-10 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
'H20 Na2 O10, C18 H12 N2 O4, C18 H10 N2 O4, 8(H2 O)'
_chemical_formula_sum            'C36 H58 N4 Na2 O26'
_chemical_formula_weight         1008.84
_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'
Na Na 0.0362 0.0249 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4109(6)
_cell_length_b                   11.1279(7)
_cell_length_c                   12.1125(10)
_cell_angle_alpha                101.580(7)
_cell_angle_beta                 98.222(6)
_cell_angle_gamma                117.146(6)
_cell_volume                     1178.13(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4205
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      25.123
_cell_measurement_theta_min      3.566
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66335
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   25.123
_exptl_transmission_factor_min   3.566
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4205
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.123
_diffrn_reflns_theta_min         3.566
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3706
_reflns_number_total             4205
_reflns_special_details          
;
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.392
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0947
_refine_ls_restrained_S_all      1.267
_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)+(0.0424P)²+3.8075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1949
_refine_ls_wR_factor_ref         0.2013
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.855(4)
 0.145(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All H(H) groups, All H(H,H,H,H) groups, All O(H) groups, All O(H,H) groups
3. Restrained distances
 H2N-N2N
 0.84 with sigma of 0.02
 O5-H5B
 0.88 with sigma of 0.02
 O5-H5A
 0.88 with sigma of 0.02
 H10B-O10
 0.87 with sigma of 0.02
 H11B-O11
 0.87 with sigma of 0.02
 H9B-O9
 0.87 with sigma of 0.02
 O6-H6B
 0.87 with sigma of 0.02
 O13-H13A
 0.87 with sigma of 0.02
 O13-H13B
 0.87 with sigma of 0.02
4.a Free rotating group:
 O11(H11A), O10(H10A), O12(H12A,H12B)
4.b Rotating group:
 O9(H9A), O8(H8A,H8B), O6(H6A), O7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
;
_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
Na1 Na 0.8326(2) 0.8496(2) 0.51826(18) 0.0296(5) Uani 1 1 d . . . . .
O4 O 0.8651(4) 0.6676(4) 0.2110(3) 0.0223(8) Uani 1 1 d . . . . .
O5 O 1.0557(4) 1.0680(4) 0.6343(3) 0.0251(8) Uani 1 1 d D . . . .
O1 O 1.2241(4) 1.0243(4) -0.2030(3) 0.0282(9) Uani 1 1 d . . . . .
O3 O 1.0408(4) 0.6413(4) 0.3129(3) 0.0293(9) Uani 1 1 d . . . . .
O9 O 1.0084(4) 0.7459(4) 0.5378(3) 0.0305(9) Uani 1 1 d D . . . .
H9A H 1.0112 0.7048 0.4668 0.046 Uiso 1 1 d GR . . . .
O2 O 1.3010(4) 0.8970(4) -0.3094(3) 0.0352(10) Uani 1 1 d . . . . .
O8 O 0.6918(4) 0.6062(4) 0.3709(3) 0.0339(9) Uani 1 1 d . . . . .
H8A H 0.7044 0.5440 0.4010 0.051 Uiso 1 1 d GR . . . .
H8B H 0.7312 0.6050 0.3100 0.051 Uiso 1 1 d GR . . . .
O6 O 0.6871(5) 0.7758(4) 0.6502(4) 0.0380(10) Uani 1 1 d D . . . .
H6A H 0.6735 0.6911 0.6586 0.057 Uiso 1 1 d GR . . . .
N2N N 0.3973(4) 0.2986(4) 0.0157(4) 0.0209(9) Uani 1 1 d D . . . .
N1N N 0.8895(4) 0.7951(4) -0.0092(4) 0.0229(10) Uani 1 1 d . . . . .
O11 O 0.8376(5) 0.4998(5) 0.5921(4) 0.0429(11) Uani 1 1 d D . . . .
H11A H 0.8848 0.4732 0.6378 0.064 Uiso 1 1 d G . . . .
O13 O 0.3803(5) 0.4857(5) 0.3098(4) 0.0448(11) Uani 1 1 d D . . . .
O7 O 0.6452(5) 0.9202(5) 0.4561(4) 0.0450(11) Uani 1 1 d . . . . .
H7A H 0.5640 0.8474 0.4011 0.067 Uiso 1 1 d GR . . . .
H7B H 0.6812 0.9864 0.4190 0.067 Uiso 1 1 d GR . . . .
O10 O 0.6257(5) 0.3101(5) 0.3832(4) 0.0488(12) Uani 1 1 d D . . . .
H10A H 0.6208 0.2289 0.3574 0.073 Uiso 1 1 d G . . . .
C12 C 1.1875(5) 0.8954(5) -0.0062(4) 0.0139(9) Uani 1 1 d . . . . .
C15 C 1.3479(5) 0.9514(5) -0.0050(4) 0.0146(9) Uani 1 1 d . . . . .
C8 C 0.9581(5) 0.6263(5) 0.2180(4) 0.0152(10) Uani 1 1 d . . . . .
C17 C 1.2991(5) 0.9642(5) -0.2145(4) 0.0166(10) Uani 1 1 d . . . . .
C16 C 1.3996(5) 0.9775(4) -0.1029(4) 0.0129(9) Uani 1 1 d . . . . .
C3 C 0.6938(5) 0.4014(5) 0.0121(4) 0.0144(9) Uani 1 1 d . . . . .
C13 C 1.1481(5) 0.9514(6) 0.0880(4) 0.0186(10) Uani 1 1 d . . . . .
C18 C 1.4495(5) 0.9758(5) 0.0965(4) 0.0134(9) Uani 1 1 d . . . . .
C2 C 0.6449(5) 0.3593(5) 0.1075(4) 0.0162(10) Uani 1 1 d . . . . .
C6 C 0.8541(5) 0.4578(5) 0.0095(4) 0.0150(10) Uani 1 1 d . . . . .
C9 C 0.8803(5) 0.4044(5) -0.0949(4) 0.0155(10) Uani 1 1 d . . . . .
C4 C 0.5892(5) 0.3878(5) -0.0806(4) 0.0174(10) Uani 1 1 d . . . . .
C7 C 0.9749(5) 0.5552(5) 0.1053(4) 0.0139(9) Uani 1 1 d . . . . .
C1 C 0.4960(5) 0.3100(5) 0.1051(4) 0.0195(10) Uani 1 1 d . . . . .
H1 H 0.4633 0.2833 0.1701 0.023 Uiso 1 1 calc R . . . .
C5 C 0.4415(5) 0.3347(5) -0.0771(5) 0.0199(11) Uani 1 1 d . . . . .
O12 O 1.3462(5) 0.8626(6) 0.3634(5) 0.0676(16) Uani 1 1 d . . . . .
H12A H 1.2611 0.7920 0.3620 0.101 Uiso 1 1 d G . . . .
H12B H 1.3535 0.9357 0.4125 0.101 Uiso 1 1 d G . . . .
C11 C 1.0733(5) 0.7868(5) -0.1004(4) 0.0193(10) Uani 1 1 d . . . . .
C14 C 0.9982(6) 0.8991(6) 0.0829(5) 0.0226(11) Uani 1 1 d . . . . .
C10 C 0.9262(5) 0.7383(5) -0.0997(5) 0.0227(11) Uani 1 1 d . . . . .
H2 H 0.703(5) 0.358(5) 0.175(4) 0.006(11) Uiso 1 1 d . . . . .
H14 H 0.968(5) 0.930(5) 0.150(4) 0.012(12) Uiso 1 1 d . . . . .
H10 H 0.839(5) 0.663(5) -0.164(4) 0.009(11) Uiso 1 1 d . . . . .
H11 H 1.099(6) 0.746(5) -0.166(5) 0.022(13) Uiso 1 1 d . . . . .
H9 H 0.792(6) 0.329(5) -0.167(4) 0.017(12) Uiso 1 1 d . . . . .
H4 H 0.618(6) 0.420(6) -0.150(5) 0.027(14) Uiso 1 1 d . . . . .
H5 H 0.370(5) 0.323(5) -0.140(4) 0.007(11) Uiso 1 1 d . . . . .
H18 H 1.420(6) 0.962(5) 0.155(5) 0.015(13) Uiso 1 1 d . . . . .
H2N H 0.303(3) 0.255(11) 0.006(10) 0.14(5) Uiso 1 1 d D . . . .
H13 H 1.212(6) 1.013(6) 0.147(5) 0.028(16) Uiso 1 1 d . . . . .
H5A H 1.059(6) 1.145(4) 0.675(4) 0.023(14) Uiso 1 1 d D . . . .
H5B H 1.121(6) 1.052(7) 0.674(5) 0.06(2) Uiso 1 1 d D . . . .
H10B H 0.688(8) 0.351(9) 0.453(4) 0.086 Uiso 1 1 d DR . . . .
H9B H 1.100(4) 0.796(8) 0.581(6) 0.086 Uiso 1 1 d DR . . . .
H11B H 0.900(8) 0.574(6) 0.574(7) 0.086 Uiso 1 1 d DR . . . .
H6B H 0.592(3) 0.745(9) 0.638(7) 0.086 Uiso 1 1 d DR . . . .
H13A H 0.467(6) 0.550(8) 0.357(7) 0.12(4) Uiso 1 1 d D . . . .
H13B H 0.322(13) 0.478(15) 0.356(10) 0.177 Uiso 1 1 d DR . . . .


_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
Na1 Na1 3.734(4) 2_776 ?
Na1 O5 2.412(4) . ?
Na1 O5 2.435(4) 2_776 ?
Na1 O9 2.579(4) . ?
Na1 O8 2.522(4) . ?
Na1 O6 2.367(5) . ?
Na1 O7 2.492(5) . ?
O4 C8 1.247(6) . ?
O5 Na1 2.435(4) 2_776 ?
O5 H5A 0.88(2) . ?
O5 H5B 0.88(2) . ?
O1 C17 1.243(6) . ?
O3 C8 1.264(6) . ?
O9 H9A 0.8999 . ?
O9 H9B 0.87(2) . ?
O2 C17 1.247(6) . ?
O8 H8A 0.8944 . ?
O8 H8B 0.8944 . ?
O6 H6A 0.9159 . ?
O6 H6B 0.87(2) . ?
N2N C1 1.324(6) . ?
N2N C5 1.340(7) . ?
N2N H2N 0.85(2) . ?
N1N C14 1.338(7) . ?
N1N C10 1.345(7) . ?
O11 H11A 0.8698 . ?
O11 H11B 0.88(2) . ?
O13 H13A 0.87(2) . ?
O13 H13B 0.87(2) . ?
O7 H7A 0.9008 . ?
O7 H7B 0.9018 . ?
O10 H10A 0.8701 . ?
O10 H10B 0.87(2) . ?
C12 C15 1.489(6) . ?
C12 C13 1.392(7) . ?
C12 C11 1.387(7) . ?
C15 C16 1.400(6) . ?
C15 C18 1.390(6) . ?
C8 C7 1.510(6) . ?
C17 C16 1.523(6) . ?
C16 C18 1.396(6) 2_875 ?
C3 C2 1.408(6) . ?
C3 C6 1.499(6) . ?
C3 C4 1.378(6) . ?
C13 C14 1.381(7) . ?
C13 H13 0.82(6) . ?
C18 C16 1.396(6) 2_875 ?
C18 H18 0.83(5) . ?
C2 C1 1.381(6) . ?
C2 H2 0.95(5) . ?
C6 C9 1.404(6) . ?
C6 C7 1.392(6) . ?
C9 C7 1.396(6) 2_765 ?
C9 H9 1.04(5) . ?
C4 C5 1.383(6) . ?
C4 H4 1.01(5) . ?
C7 C9 1.396(6) 2_765 ?
C1 H1 0.9500 . ?
C5 H5 0.93(5) . ?
O12 H12A 0.8704 . ?
O12 H12B 0.8701 . ?
C11 C10 1.374(7) . ?
C11 H11 0.97(5) . ?
C14 H14 0.97(5) . ?
C10 H10 0.98(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Na1 Na1 39.85(9) . 2_776 ?
O5 Na1 Na1 39.41(9) 2_776 2_776 ?
O5 Na1 O5 79.26(14) . 2_776 ?
O5 Na1 O9 83.22(13) . . ?
O5 Na1 O9 85.86(14) 2_776 . ?
O5 Na1 O8 154.23(15) . . ?
O5 Na1 O8 86.33(14) 2_776 . ?
O5 Na1 O7 87.34(14) 2_776 . ?
O5 Na1 O7 105.03(16) . . ?
O9 Na1 Na1 82.92(11) . 2_776 ?
O8 Na1 Na1 122.69(13) . 2_776 ?
O8 Na1 O9 74.46(13) . . ?
O6 Na1 Na1 144.03(15) . 2_776 ?
O6 Na1 O5 169.15(17) . 2_776 ?
O6 Na1 O5 105.15(16) . . ?
O6 Na1 O9 104.39(15) . . ?
O6 Na1 O8 92.94(15) . . ?
O6 Na1 O7 81.95(15) . . ?
O7 Na1 Na1 97.89(13) . 2_776 ?
O7 Na1 O9 168.14(16) . . ?
O7 Na1 O8 95.43(16) . . ?
Na1 O5 Na1 100.74(14) . 2_776 ?
Na1 O5 H5A 126(3) . . ?
Na1 O5 H5A 100(3) 2_776 . ?
Na1 O5 H5B 103(5) 2_776 . ?
Na1 O5 H5B 112(5) . . ?
H5A O5 H5B 110(6) . . ?
Na1 O9 H9A 110.7 . . ?
Na1 O9 H9B 122(6) . . ?
H9A O9 H9B 107.2 . . ?
Na1 O8 H8A 110.5 . . ?
Na1 O8 H8B 110.6 . . ?
H8A O8 H8B 103.4 . . ?
Na1 O6 H6A 112.2 . . ?
Na1 O6 H6B 127(6) . . ?
H6A O6 H6B 90.6 . . ?
C1 N2N C5 119.5(4) . . ?
C1 N2N H2N 124(8) . . ?
C5 N2N H2N 115(8) . . ?
C14 N1N C10 119.5(4) . . ?
H11A O11 H11B 111.4 . . ?
H13A O13 H13B 102(10) . . ?
Na1 O7 H7A 110.9 . . ?
Na1 O7 H7B 110.9 . . ?
H7A O7 H7B 103.2 . . ?
H10A O10 H10B 106.1 . . ?
C13 C12 C15 120.6(4) . . ?
C11 C12 C15 121.4(4) . . ?
C11 C12 C13 118.0(4) . . ?
C16 C15 C12 122.4(4) . . ?
C18 C15 C12 118.8(4) . . ?
C18 C15 C16 118.8(4) . . ?
O4 C8 O3 124.6(4) . . ?
O4 C8 C7 117.8(4) . . ?
O3 C8 C7 117.6(4) . . ?
O1 C17 O2 125.5(4) . . ?
O1 C17 C16 116.8(4) . . ?
O2 C17 C16 117.7(4) . . ?
C15 C16 C17 122.4(4) . . ?
C18 C16 C15 119.0(4) 2_875 . ?
C18 C16 C17 118.5(4) 2_875 . ?
C2 C3 C6 121.5(4) . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 C6 120.5(4) . . ?
C12 C13 H13 121(4) . . ?
C14 C13 C12 119.1(5) . . ?
C14 C13 H13 120(4) . . ?
C15 C18 C16 122.1(4) . 2_875 ?
C15 C18 H18 119(3) . . ?
C16 C18 H18 119(3) 2_875 . ?
C3 C2 H2 127(3) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 115(3) . . ?
C9 C6 C3 117.0(4) . . ?
C7 C6 C3 123.4(4) . . ?
C7 C6 C9 119.6(4) . . ?
C6 C9 H9 121(3) . . ?
C7 C9 C6 121.8(4) 2_765 . ?
C7 C9 H9 117(3) 2_765 . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4 122(3) . . ?
C5 C4 H4 118(3) . . ?
C6 C7 C8 123.4(4) . . ?
C6 C7 C9 118.6(4) . 2_765 ?
C9 C7 C8 118.0(4) 2_765 . ?
N2N C1 C2 122.5(5) . . ?
N2N C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
N2N C5 C4 121.6(5) . . ?
N2N C5 H5 119(3) . . ?
C4 C5 H5 120(3) . . ?
H12A O12 H12B 104.5 . . ?
C12 C11 H11 119(3) . . ?
C10 C11 C12 120.2(5) . . ?
C10 C11 H11 121(3) . . ?
N1N C14 C13 122.0(5) . . ?
N1N C14 H14 117(3) . . ?
C13 C14 H14 120(3) . . ?
N1N C10 C11 121.2(5) . . ?
N1N C10 H10 114(3) . . ?
C11 C10 H10 125(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9A O3 0.90 1.98 2.870(5) 171.9 .
O8 H8B O4 0.89 1.95 2.807(5) 160.5 .
O6 H6A O13 0.92 1.92 2.828(6) 170.0 2_666
O7 H7A O12 0.90 2.34 2.873(7) 118.0 1_455
O10 H10A O2 0.87 1.95 2.770(6) 155.7 2_765
N2N H2N N1N 0.85(2) 1.83(4) 2.659(5) 165(11) 2_665
O10 H10B O11 0.87(2) 1.95(4) 2.781(7) 160(8) .
O9 H9B O2 0.87(2) 1.96(2) 2.827(5) 174(8) 1_556

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.855(4)
2 0.145(4)
