# 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_H2L
_database_code_depnum_ccdc_archive 'CCDC 1858827'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2018-07-27 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 N2 O3'
_chemical_formula_weight         250.29

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'
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'

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

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

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

_cell_length_a                   5.3989(3)
_cell_length_b                   10.1581(5)
_cell_length_c                   23.3868(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.508(2)
_cell_angle_gamma                90
_cell_volume                     1282.54(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      68.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.002
_exptl_absorpt_coefficient_mu    0.761
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6648
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker CCD Smart 6000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22929
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.780
_diffrn_reflns_theta_max         68.383
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2316
_reflns_number_gt                2115
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1474P)²+0.4208P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2316
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.2145
_refine_ls_wR_factor_gt          0.2082
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1447(3) 0.64487(15) 0.47656(6) 0.0525(5) Uani 1 1 d . . . . .
N2 N 0.2577(3) 0.53526(18) 0.55470(8) 0.0436(5) Uani 1 1 d . . . . .
C8 C 0.2952(4) 0.63093(19) 0.51636(8) 0.0413(5) Uani 1 1 d . . . . .
C2 C 0.5440(4) 0.37997(19) 0.67799(8) 0.0421(5) Uani 1 1 d . . . . .
C1 C 0.3807(4) 0.41219(19) 0.63021(8) 0.0426(5) Uani 1 1 d . . . . .
H1 H 0.2450 0.3586 0.6223 0.051 Uiso 1 1 calc R U . . .
O2 O 1.0703(3) 1.13538(17) 0.57593(7) 0.0590(5) Uani 1 1 d . . . . .
C7 C 0.4880(4) 0.2723(2) 0.71282(10) 0.0506(5) Uani 1 1 d . . . . .
H7 H 0.3479 0.2220 0.7049 0.061 Uiso 1 1 calc R U . . .
C3 C 0.7578(4) 0.4542(2) 0.69046(9) 0.0457(5) Uani 1 1 d . . . . .
C9 C 0.5184(4) 0.7179(2) 0.52327(9) 0.0457(5) Uani 1 1 d . . . . .
H9A H 0.5588 0.7552 0.4863 0.055 Uiso 1 1 calc R U . . .
H9B H 0.6577 0.6643 0.5355 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6373(5) 0.2394(2) 0.75880(10) 0.0584(6) Uani 1 1 d . . . . .
H6 H 0.5972 0.1679 0.7818 0.070 Uiso 1 1 calc R U . . .
C5 C 0.8466(5) 0.3131(3) 0.77061(10) 0.0599(6) Uani 1 1 d . . . . .
H5 H 0.9478 0.2909 0.8015 0.072 Uiso 1 1 calc R U . . .
C10 C 0.4850(4) 0.8293(2) 0.56581(10) 0.0507(6) Uani 1 1 d . . . . .
H10A H 0.4287 0.7941 0.6020 0.061 Uiso 1 1 calc R U . . .
H10B H 0.3605 0.8902 0.5516 0.061 Uiso 1 1 calc R U . . .
C4 C 0.9061(4) 0.4194(2) 0.73674(10) 0.0554(6) Uani 1 1 d . . . . .
H4 H 1.0475 0.4684 0.7450 0.066 Uiso 1 1 calc R U . . .
C13 C 0.9542(4) 1.0860(2) 0.62538(10) 0.0541(6) Uani 1 1 d . . . . .
H13A H 0.9282 1.1584 0.6517 0.065 Uiso 1 1 calc R U . . .
H13B H 1.0658 1.0241 0.6439 0.065 Uiso 1 1 calc R U . . .
C12 C 0.7094(4) 1.0182(2) 0.61492(10) 0.0551(6) Uani 1 1 d . . . . .
H12A H 0.5929 1.0812 0.5989 0.066 Uiso 1 1 calc R U . . .
H12B H 0.6441 0.9882 0.6512 0.066 Uiso 1 1 calc R U . . .
C11 C 0.7304(4) 0.9018(2) 0.57475(10) 0.0531(6) Uani 1 1 d . . . . .
H11A H 0.8521 0.8407 0.5900 0.064 Uiso 1 1 calc R U . . .
H11B H 0.7895 0.9325 0.5380 0.064 Uiso 1 1 calc R U . . .
N1 N 0.4208(3) 0.51304(16) 0.59903(7) 0.0424(5) Uani 1 1 d . . . . .
O3 O 0.8266(5) 0.5566(3) 0.65828(13) 0.1016(8) Uani 1 1 d . . . . .
H3OA H 0.7167 0.5735 0.6350 0.152 Uiso 1 1 calc R U . . .
H1O H 0.968(7) 1.190(4) 0.5563(14) 0.080(10) Uiso 1 1 d . . . . .
H2N H 0.164(5) 0.491(3) 0.5500(11) 0.041(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.238(2) . ?
N2 C8 1.339(3) . ?
N2 N1 1.373(2) . ?
C8 C9 1.502(3) . ?
C2 C7 1.399(3) . ?
C2 C3 1.407(3) . ?
C2 C1 1.455(3) . ?
C1 N1 1.277(3) . ?
O2 C13 1.413(3) . ?
C7 C6 1.379(3) . ?
C3 O3 1.339(3) . ?
C3 C4 1.386(3) . ?
C9 C10 1.518(3) . ?
C6 C5 1.382(4) . ?
C5 C4 1.379(4) . ?
C10 C11 1.529(3) . ?
C13 C12 1.508(3) . ?
C12 C11 1.515(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
C8 N2 N1 121.68(17) . . ?
O1 C8 N2 118.96(17) . . ?
O1 C8 C9 122.30(18) . . ?
N2 C8 C9 118.74(18) . . ?
C7 C2 C3 118.64(19) . . ?
C7 C2 C1 119.39(18) . . ?
C3 C2 C1 121.96(19) . . ?
N1 C1 C2 120.96(18) . . ?
C6 C7 C2 121.0(2) . . ?
O3 C3 C4 118.4(2) . . ?
O3 C3 C2 122.1(2) . . ?
C4 C3 C2 119.5(2) . . ?
C8 C9 C10 114.16(17) . . ?
C7 C6 C5 119.7(2) . . ?
C4 C5 C6 120.3(2) . . ?
C9 C10 C11 109.95(18) . . ?
C5 C4 C3 120.8(2) . . ?
O2 C13 C12 115.09(19) . . ?
C13 C12 C11 112.71(19) . . ?
C12 C11 C10 113.04(19) . . ?
C1 N1 N2 116.89(17) . . ?

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
N1 N2 C8 O1 178.54(18) . . . . ?
N1 N2 C8 C9 -1.6(3) . . . . ?
C7 C2 C1 N1 177.07(18) . . . . ?
C3 C2 C1 N1 -2.9(3) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C1 C2 C7 C6 -179.43(19) . . . . ?
C7 C2 C3 O3 178.4(2) . . . . ?
C1 C2 C3 O3 -1.7(3) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 179.64(19) . . . . ?
O1 C8 C9 C10 98.0(2) . . . . ?
N2 C8 C9 C10 -81.8(2) . . . . ?
C2 C7 C6 C5 -0.5(4) . . . . ?
C7 C6 C5 C4 0.2(4) . . . . ?
C8 C9 C10 C11 173.56(18) . . . . ?
C6 C5 C4 C3 0.0(4) . . . . ?
O3 C3 C4 C5 -178.7(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
O2 C13 C12 C11 59.0(3) . . . . ?
C13 C12 C11 C10 177.7(2) . . . . ?
C9 C10 C11 C12 177.63(19) . . . . ?
C2 C1 N1 N2 179.63(17) . . . . ?
C8 N2 N1 C1 -173.80(18) . . . . ?

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
O2 H1O O1 0.91(4) 1.94(4) 2.795(2) 157(3) 3_676
N2 H2N O1 0.68(3) 2.25(3) 2.928(2) 173(3) 3_566
C1 H1 O2 0.93 2.68 3.505(2) 148.2 1_445
O3 H3OA N1 0.82 1.90 2.620(3) 145.7 .
O3 H3OA N1 0.82 1.90 2.620(3) 145.7 .
C1 H1 O2 0.93 2.68 3.505(2) 148.2 1_445
N2 H2N O1 0.68(3) 2.25(3) 2.928(2) 173(3) 3_566
O2 H1O O1 0.91(4) 1.94(4) 2.795(2) 157(3) 3_676
O3 H3OA N1 0.82 1.90 2.620(3) 145.7 .
O2 H1O O1 0.91(4) 1.94(4) 2.795(2) 157(3) 3_676
N2 H2N O1 0.68(3) 2.25(3) 2.928(2) 173(3) 3_566

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4


# start Validation Reply Form
_vrf_PLAT230_H2L                 
;
PROBLEM: Hirshfeld Test Diff for   O3       --C3        .       21.5 s.u.  
RESPONSE: The model has been established in base on the spectroscopic and 
analytical data. We have searched for alternative positions for the O3 
atom as cause of the large anisotropical factors but those attempts were 
unsuccessfull. Although a possible disorder can be due to proton transfer 
from the O(3)-H to N(1), the observed bond distances involving both heavy 
atoms don't support that model. 
;
####################################################################### 
# 
# 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_Zn1
_database_code_depnum_ccdc_archive 'CCDC 1858828'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2018-07-27 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H41 N5 O10 Zn'
_chemical_formula_weight         673.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.6157(14)
_cell_length_b                   14.5331(16)
_cell_length_c                   18.1322(19)
_cell_angle_alpha                109.291(3)
_cell_angle_beta                 110.987(3)
_cell_angle_gamma                95.422(3)
_cell_volume                     3068.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9512
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.47

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    0.864
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6325
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS-2014/4 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            87023
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.310
_diffrn_reflns_theta_max         26.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             12633
_reflns_number_gt                10390
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+25.6705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         12633
_refine_ls_number_parameters     821
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0901
_refine_ls_wR_factor_ref         0.2389
_refine_ls_wR_factor_gt          0.2286
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N21 N 0.4871(5) 0.1892(5) 0.4541(4) 0.0424(15) Uani 1 1 d . . . . .
O51 O 0.5461(6) 0.1405(5) 0.4288(5) 0.0663(18) Uani 1 1 d . . . . .
O52 O 0.4985(4) 0.2800(4) 0.4650(4) 0.0523(14) Uani 1 1 d . . . . .
O53 O 0.4136(4) 0.1482(4) 0.4658(4) 0.0448(12) Uani 1 1 d . . . . .
C64 C 0.2475(9) 0.3994(7) 0.1516(6) 0.071(3) Uani 1 1 d . . . . .
H64A H 0.3000 0.3584 0.1623 0.106 Uiso 1 1 calc R U . . .
H64B H 0.2392 0.4346 0.2045 0.106 Uiso 1 1 calc R U . . .
H64C H 0.2735 0.4486 0.1324 0.106 Uiso 1 1 calc R U . . .
C63 C 0.1418(8) 0.3340(6) 0.0843(5) 0.050(2) Uani 1 1 d . . . . .
H63A H 0.1063 0.2982 0.1095 0.060 Uiso 1 1 calc R U . . .
H63B H 0.0948 0.3761 0.0637 0.060 Uiso 1 1 calc R U . . .
O15 O 0.1519(4) 0.2618(3) 0.0130(3) 0.0351(11) Uani 1 1 d . . . . .
H15 H 0.2103 0.2825 0.0110 0.053 Uiso 1 1 calc R U . . .
C60 C 0.6405(8) 0.5169(7) 0.5937(6) 0.060(2) Uani 1 1 d . . . . .
H60A H 0.6385 0.5680 0.5693 0.091 Uiso 1 1 calc R U . . .
H60B H 0.6613 0.5496 0.6556 0.091 Uiso 1 1 calc R U . . .
H60C H 0.5686 0.4709 0.5664 0.091 Uiso 1 1 calc R U . . .
C61 C 0.7197(7) 0.4603(7) 0.5784(5) 0.054(2) Uani 1 1 d . . . . .
H61A H 0.7897 0.5087 0.5999 0.065 Uiso 1 1 calc R U . . .
H61B H 0.7310 0.4183 0.6126 0.065 Uiso 1 1 calc R U . . .
O40 O 0.6911(4) 0.3975(4) 0.4918(3) 0.0419(12) Uani 1 1 d . . . . .
H40 H 0.6450 0.3452 0.4777 0.063 Uiso 1 1 calc R U . . .
Zn1 Zn 0.84813(5) 0.14471(5) 0.08865(4) 0.02067(18) Uani 1 1 d . . . . .
Zn2 Zn 0.02693(6) 0.26460(5) 0.40451(4) 0.0252(2) Uani 1 1 d . . . . .
O6 O 0.0210(4) 0.3266(3) 0.3161(3) 0.0264(9) Uani 1 1 d D . . . .
H601 H 0.018(6) 0.289(5) 0.274(4) 0.032 Uiso 1 1 d D U . . .
O3 O 0.8872(4) 0.1856(3) -0.0016(3) 0.0295(9) Uani 1 1 d . . . . .
O4 O 0.7035(3) 0.0352(3) -0.0023(3) 0.0247(9) Uani 1 1 d . . . . .
O8 O 0.7961(3) 0.1544(3) 0.1848(3) 0.0240(8) Uani 1 1 d D . . . .
O2 O -0.0198(4) 0.2244(4) 0.4927(3) 0.0348(10) Uani 1 1 d . . . . .
O1 O 0.1701(4) 0.3711(3) 0.5031(3) 0.0319(10) Uani 1 1 d . . . . .
O7 O 1.0074(3) 0.2019(3) 0.1822(3) 0.0236(8) Uani 1 1 d . . . . .
O5 O -0.0732(3) 0.1292(3) 0.3043(3) 0.0241(8) Uani 1 1 d . . . . .
N7 N 0.8978(4) 0.0082(3) 0.0652(3) 0.0176(9) Uani 1 1 d . . . . .
N5 N 0.7860(4) 0.2723(3) 0.0902(3) 0.0223(10) Uani 1 1 d . . . . .
N3 N -0.0871(4) 0.3497(4) 0.4230(3) 0.0252(11) Uani 1 1 d . . . . .
N8 N 0.8109(4) -0.0733(3) 0.0112(3) 0.0192(9) Uani 1 1 d . . . . .
H801 H 0.817(5) -0.147(5) -0.005(4) 0.023 Uiso 1 1 d . U . . .
N1 N 0.1474(4) 0.1848(4) 0.4057(3) 0.0247(10) Uani 1 1 d . . . . .
C18 C 0.9923(4) -0.0111(4) 0.0894(3) 0.0184(10) Uani 1 1 d . . . . .
H18 H 0.9967 -0.0789 0.0669 0.022 Uiso 1 1 calc R U . . .
C19 C 1.0911(4) 0.0639(4) 0.1483(3) 0.0185(10) Uani 1 1 d . . . . .
C31 C 0.5880(5) 0.3056(5) 0.2681(4) 0.0281(13) Uani 1 1 d . . . . .
H31 H 0.5420 0.3411 0.2889 0.034 Uiso 1 1 calc R U . . .
C23 C 1.1982(5) 0.2308(5) 0.2515(4) 0.0278(13) Uani 1 1 d . . . . .
H23 H 1.2023 0.2995 0.2810 0.033 Uiso 1 1 calc R U . . .
C17 C 0.7132(5) -0.0535(4) -0.0192(3) 0.0223(11) Uani 1 1 d . . . . .
C21 C 1.2876(5) 0.0961(5) 0.2237(4) 0.0291(13) Uani 1 1 d . . . . .
H21 H 1.3521 0.0726 0.2342 0.035 Uiso 1 1 calc R U . . .
C26 C 0.7282(4) 0.3145(4) 0.1280(4) 0.0219(11) Uani 1 1 d . . . . .
H26 H 0.7066 0.3714 0.1186 0.026 Uiso 1 1 calc R U . . .
C2 C 0.1433(5) 0.0920(5) 0.3661(4) 0.0271(12) Uani 1 1 d . . . . .
H2 H 0.2098 0.0721 0.3760 0.032 Uiso 1 1 calc R U . . .
N6 N 0.8094(5) 0.3128(4) 0.0375(4) 0.0284(11) Uani 1 1 d . . . . .
H61 H 0.790(6) 0.362(6) 0.034(5) 0.034 Uiso 1 1 d . U . . .
C29 C 0.6848(5) 0.1762(4) 0.2617(4) 0.0241(12) Uani 1 1 d . . . . .
H29 H 0.7037 0.1219 0.2773 0.029 Uiso 1 1 calc R U . . .
N2 N 0.2496(4) 0.2457(4) 0.4631(3) 0.0291(11) Uani 1 1 d . . . . .
H30 H 0.294(6) 0.214(6) 0.463(5) 0.035 Uiso 1 1 d . U . . .
C8 C -0.0372(5) -0.1631(5) 0.2211(4) 0.0300(13) Uani 1 1 d . . . . .
H8 H -0.0295 -0.2299 0.2004 0.036 Uiso 1 1 calc R U . . .
C6 C -0.1508(5) -0.0452(4) 0.2250(4) 0.0237(12) Uani 1 1 d . . . . .
H6 H -0.2213 -0.0332 0.2066 0.028 Uiso 1 1 calc R U . . .
C15 C 0.0124(5) 0.4443(4) 0.2510(4) 0.0278(13) Uani 1 1 d . . . . .
H1 H 0.0547 0.4128 0.2232 0.033 Uiso 1 1 calc R U . . .
C27 C 0.6943(4) 0.2809(4) 0.1837(3) 0.0192(11) Uani 1 1 d . . . . .
N4 N -0.1370(4) 0.3212(4) 0.4687(3) 0.0291(11) Uani 1 1 d . . . . .
H41 H -0.201(6) 0.339(5) 0.471(5) 0.035 Uiso 1 1 d . U . . .
C13 C -0.0829(6) 0.5738(5) 0.2774(5) 0.0359(15) Uani 1 1 d . . . . .
H13 H -0.1064 0.6301 0.2680 0.043 Uiso 1 1 calc R U . . .
C28 C 0.7266(4) 0.2030(4) 0.2088(3) 0.0197(11) Uani 1 1 d . . . . .
C24 C 1.0973(4) 0.1657(4) 0.1933(4) 0.0209(11) Uani 1 1 d . . . . .
C11 C -0.0746(4) 0.4557(4) 0.3477(3) 0.0240(12) Uani 1 1 d . . . . .
C7 C -0.0610(4) 0.0360(4) 0.2799(3) 0.0209(11) Uani 1 1 d . . . . .
C9 C -0.1007(5) 0.2551(5) 0.4996(4) 0.0330(14) Uani 1 1 d . . . . .
C5 C -0.1391(5) -0.1429(4) 0.1968(4) 0.0262(12) Uani 1 1 d . . . . .
H5 H -0.2016 -0.1967 0.1604 0.031 Uiso 1 1 calc R U . . .
C25 C 0.8585(6) 0.2619(5) -0.0093(5) 0.0353(15) Uani 1 1 d . . . . .
C32 C 0.6258(5) 0.3321(4) 0.2149(4) 0.0252(12) Uani 1 1 d . . . . .
H32 H 0.6052 0.3859 0.1992 0.030 Uiso 1 1 calc R U . . .
C20 C 1.1875(5) 0.0312(4) 0.1652(4) 0.0247(12) Uani 1 1 d . . . . .
H20 H 1.1843 -0.0374 0.1359 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0128(4) 0.4075(4) 0.3053(4) 0.0226(11) Uani 1 1 d . . . . .
C3 C 0.0435(5) 0.0157(4) 0.3071(4) 0.0225(11) Uani 1 1 d . . . . .
C1 C 0.2514(5) 0.3398(5) 0.5128(4) 0.0293(13) Uani 1 1 d . . . . .
C10 C -0.1129(5) 0.4208(4) 0.4004(4) 0.0261(12) Uani 1 1 d . . . . .
H10 H -0.1613 0.4537 0.4198 0.031 Uiso 1 1 calc R U . . .
C30 C 0.6173(5) 0.2269(5) 0.2911(4) 0.0263(12) Uani 1 1 d . . . . .
H3 H 0.5908 0.2080 0.3272 0.032 Uiso 1 1 calc R U . . .
C12 C -0.1078(5) 0.5393(5) 0.3312(4) 0.0334(14) Uani 1 1 d . . . . .
H12 H -0.1493 0.5726 0.3590 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0532(5) -0.0837(5) 0.2762(4) 0.0270(12) Uani 1 1 d . . . . .
H4 H 0.1231 -0.0970 0.2933 0.032 Uiso 1 1 calc R U . . .
C22 C 1.2912(5) 0.1971(5) 0.2668(4) 0.0306(13) Uani 1 1 d . . . . .
H22 H 1.3588 0.2426 0.3070 0.037 Uiso 1 1 calc R U . . .
C14 C -0.0223(5) 0.5252(5) 0.2362(4) 0.0316(14) Uani 1 1 d . . . . .
H14 H -0.0048 0.5478 0.1978 0.038 Uiso 1 1 calc R U . . .
C41 C 0.5913(5) -0.1885(5) -0.0130(4) 0.0306(13) Uani 1 1 d . . . . .
H41A H 0.5358 -0.2526 -0.0498 0.037 Uiso 1 1 calc R U . . .
H41B H 0.6573 -0.2040 0.0217 0.037 Uiso 1 1 calc R U . . .
O10 O -0.1609(5) -0.2084(4) 0.3845(4) 0.0566(15) Uani 1 1 d . . . . .
H10A H -0.1189 -0.2256 0.4216 0.085 Uiso 1 1 calc R U . . .
C40 C 0.6185(5) -0.1427(5) -0.0710(4) 0.0290(13) Uani 1 1 d . . . . .
H40A H 0.6353 -0.1941 -0.1134 0.035 Uiso 1 1 calc R U . . .
H40B H 0.5547 -0.1223 -0.1029 0.035 Uiso 1 1 calc R U . . .
C42 C 0.5504(5) -0.1219(6) 0.0466(4) 0.0368(15) Uani 1 1 d . . . . .
H42A H 0.4816 -0.1098 0.0124 0.044 Uiso 1 1 calc R U . . .
H42B H 0.6039 -0.0563 0.0817 0.044 Uiso 1 1 calc R U . . .
C35 C -0.1615(6) 0.2160(6) 0.5422(5) 0.0389(16) Uani 1 1 d . . . . .
H35A H -0.2343 0.2300 0.5248 0.047 Uiso 1 1 calc R U . . .
H35B H -0.1224 0.2517 0.6053 0.047 Uiso 1 1 calc R U . . .
O11 O 0.3946(6) -0.0941(7) 0.1384(5) 0.079(2) Uani 1 1 d . . . . .
H11 H 0.3841 -0.0814 0.0946 0.118 Uiso 1 1 calc R U . . .
C45 C 0.3621(6) 0.3988(6) 0.5830(5) 0.0405(16) Uani 1 1 d . . . . .
H45A H 0.3682 0.4715 0.5966 0.049 Uiso 1 1 calc R U . . .
H45B H 0.4188 0.3795 0.5630 0.049 Uiso 1 1 calc R U . . .
C43 C 0.5313(6) -0.1698(7) 0.1066(5) 0.0477(19) Uani 1 1 d . . . . .
H43A H 0.4735 -0.2326 0.0710 0.057 Uiso 1 1 calc R U . . .
H43B H 0.5984 -0.1880 0.1360 0.057 Uiso 1 1 calc R U . . .
C38 C -0.2490(6) -0.0727(6) 0.3982(5) 0.0457(18) Uani 1 1 d . . . . .
H38A H -0.2850 -0.0934 0.4308 0.055 Uiso 1 1 calc R U . . .
H38B H -0.2966 -0.1088 0.3363 0.055 Uiso 1 1 calc R U . . .
C39 C -0.1420(6) -0.1026(6) 0.4170(5) 0.0463(18) Uani 1 1 d . . . . .
H39A H -0.1016 -0.0754 0.3899 0.056 Uiso 1 1 calc R U . . .
H39B H -0.0977 -0.0742 0.4797 0.056 Uiso 1 1 calc R U . . .
C44 C 0.5001(7) -0.1048(7) 0.1724(6) 0.0498(19) Uani 1 1 d . . . . .
H44A H 0.5073 -0.1336 0.2160 0.060 Uiso 1 1 calc R U . . .
H44B H 0.5508 -0.0375 0.2017 0.060 Uiso 1 1 calc R U . . .
C49 C 0.7612(7) 0.2477(7) -0.1635(6) 0.053(2) Uani 1 1 d . . . . .
H49A H 0.7456 0.1739 -0.1809 0.063 Uiso 1 1 calc R U . . .
H49B H 0.7001 0.2709 -0.1520 0.063 Uiso 1 1 calc R U . . .
C46 C 0.3799(7) 0.3775(7) 0.6657(5) 0.055(2) Uani 1 1 d . . . . .
H46A H 0.3248 0.4003 0.6866 0.066 Uiso 1 1 calc R U . . .
H46B H 0.3678 0.3041 0.6501 0.066 Uiso 1 1 calc R U . . .
C36 C -0.1739(6) 0.1020(6) 0.5183(4) 0.0373(15) Uani 1 1 d . . . . .
H36A H -0.1010 0.0886 0.5383 0.045 Uiso 1 1 calc R U . . .
H36B H -0.2130 0.0801 0.5486 0.045 Uiso 1 1 calc R U . . .
C37 C -0.2352(6) 0.0400(5) 0.4217(5) 0.0401(16) Uani 1 1 d . . . . .
H37A H -0.3077 0.0542 0.4015 0.048 Uiso 1 1 calc R U . . .
H37B H -0.1956 0.0612 0.3914 0.048 Uiso 1 1 calc R U . . .
C48 C 0.8696(8) 0.2978(6) -0.0766(7) 0.058(3) Uani 1 1 d . . . . .
H48A H 0.9324 0.2791 -0.0879 0.070 Uiso 1 1 calc R U . . .
H48B H 0.8823 0.3719 -0.0551 0.070 Uiso 1 1 calc R U . . .
C47 C 0.4901(6) 0.4278(6) 0.7373(5) 0.0451(18) Uani 1 1 d . . . . .
H47A H 0.4987 0.5014 0.7577 0.054 Uiso 1 1 calc R U . . .
H47B H 0.5453 0.4116 0.7147 0.054 Uiso 1 1 calc R U . . .
O12 O 0.6747(5) 0.0630(5) -0.3702(5) 0.0602(16) Uani 1 1 d . . . . .
H12A H 0.6517 0.0038 -0.3768 0.072 Uiso 1 1 calc R U . . .
O13 O 0.4951(7) 0.5497(5) 0.9098(5) 0.078(2) Uani 1 1 d D . . . .
H990 H 0.5605 0.5642 0.9441 0.094 Uiso 1 1 calc R U . . .
C51 C 0.6582(8) 0.2328(8) -0.3184(6) 0.067(3) Uani 1 1 d . . . . .
H51A H 0.6071 0.2726 -0.3053 0.080 Uiso 1 1 calc R U . . .
H51B H 0.6703 0.2444 -0.3656 0.080 Uiso 1 1 calc R U . . .
C50 C 0.7670(9) 0.2719(8) -0.2384(6) 0.063(3) Uani 1 1 d . . . . .
H50A H 0.8224 0.2419 -0.2544 0.076 Uiso 1 1 calc R U . . .
H50B H 0.7905 0.3456 -0.2190 0.076 Uiso 1 1 calc R U . . .
C53 C 0.5116(7) 0.3975(6) 0.8130(6) 0.0507(19) Uani 1 1 d . . . . .
H53A H 0.5908 0.4156 0.8480 0.061 Uiso 1 1 calc R U . . .
H53B H 0.4862 0.3236 0.7911 0.061 Uiso 1 1 calc R U . . .
C52 C 0.6051(7) 0.1213(8) -0.3499(6) 0.060(2) Uani 1 1 d . . . . .
H52A H 0.5886 0.1089 -0.3046 0.072 Uiso 1 1 calc R U . . .
H52B H 0.5362 0.1023 -0.4013 0.072 Uiso 1 1 calc R U . . .
C54 C 0.4566(9) 0.4464(5) 0.8704(6) 0.069(3) Uani 1 1 d D . . . .
H54A H 0.3775 0.4298 0.8355 0.082 Uiso 1 1 calc R U . . .
H54B H 0.4687 0.4184 0.9150 0.082 Uiso 1 1 calc R U . . .
H7 H 0.843(6) 0.154(6) 0.224(4) 0.04(2) Uiso 1 1 d D . . . .
N20 N 0.7752(5) 0.5500(4) 1.0407(4) 0.0343(13) Uani 1 1 d . . . . .
O56 O 0.7349(5) 0.6258(4) 1.0413(4) 0.0558(16) Uani 1 1 d . . . . .
O54 O 0.7130(5) 0.4706(4) 1.0265(4) 0.0487(14) Uani 1 1 d . . . . .
O55 O 0.8675(5) 0.5538(4) 1.0494(4) 0.0558(15) 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
N21 O51 1.231(8) . ?
N21 O53 1.234(8) . ?
N21 O52 1.254(9) . ?
C64 C63 1.476(12) . ?
C63 O15 1.431(8) . ?
C60 C61 1.465(13) . ?
C61 O40 1.415(9) . ?
Zn1 O8 2.074(4) . ?
Zn1 O7 2.089(4) . ?
Zn1 N5 2.106(5) . ?
Zn1 N7 2.115(4) . ?
Zn1 O4 2.117(4) . ?
Zn1 O3 2.126(4) . ?
Zn2 O6 2.066(4) . ?
Zn2 N1 2.095(5) . ?
Zn2 O5 2.095(4) . ?
Zn2 O1 2.120(4) . ?
Zn2 N3 2.124(5) . ?
Zn2 O2 2.140(5) . ?
O6 C16 1.349(7) . ?
O3 C25 1.244(8) . ?
O4 C17 1.254(7) . ?
O8 C28 1.343(7) . ?
O2 C9 1.258(8) . ?
O1 C1 1.214(8) . ?
O7 C24 1.353(7) . ?
O5 C7 1.325(7) . ?
N7 C18 1.294(7) . ?
N7 N8 1.379(6) . ?
N5 C26 1.290(7) . ?
N5 N6 1.382(7) . ?
N3 C10 1.267(8) . ?
N3 N4 1.377(7) . ?
N8 C17 1.345(7) . ?
N1 C2 1.287(8) . ?
N1 N2 1.386(7) . ?
C18 C19 1.436(8) . ?
C19 C20 1.404(8) . ?
C19 C24 1.410(8) . ?
C31 C32 1.381(9) . ?
C31 C30 1.386(9) . ?
C23 C22 1.369(9) . ?
C23 C24 1.398(8) . ?
C17 C40 1.496(8) . ?
C21 C20 1.390(9) . ?
C21 C22 1.404(9) . ?
C26 C27 1.444(8) . ?
C2 C3 1.453(8) . ?
N6 C25 1.342(8) . ?
C29 C30 1.375(8) . ?
C29 C28 1.412(8) . ?
N2 C1 1.359(8) . ?
C8 C5 1.389(9) . ?
C8 C4 1.391(9) . ?
C6 C5 1.387(8) . ?
C6 C7 1.400(8) . ?
C15 C14 1.378(9) . ?
C15 C16 1.388(8) . ?
C27 C28 1.405(8) . ?
C27 C32 1.406(8) . ?
N4 C9 1.314(9) . ?
C13 C12 1.358(10) . ?
C13 C14 1.394(9) . ?
C11 C16 1.418(8) . ?
C11 C12 1.422(9) . ?
C11 C10 1.437(8) . ?
C7 C3 1.424(8) . ?
C9 C35 1.505(9) . ?
C25 C48 1.524(9) . ?
C3 C4 1.404(8) . ?
C1 C45 1.512(9) . ?
C41 C42 1.501(10) . ?
C41 C40 1.543(8) . ?
O10 C39 1.413(9) . ?
C42 C43 1.552(10) . ?
C35 C36 1.543(10) . ?
O11 C44 1.392(10) . ?
C45 C46 1.571(12) . ?
C43 C44 1.479(12) . ?
C38 C39 1.512(11) . ?
C38 C37 1.524(11) . ?
C49 C50 1.536(11) . ?
C49 C48 1.601(14) . ?
C46 C47 1.498(11) . ?
C36 C37 1.532(10) . ?
C47 C53 1.516(11) . ?
O12 C52 1.394(10) . ?
O13 C54 1.383(2) . ?
C51 C52 1.532(15) . ?
C51 C50 1.542(14) . ?
C53 C54 1.523(13) . ?
N20 O55 1.203(8) . ?
N20 O54 1.256(7) . ?
N20 O56 1.274(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
O51 N21 O53 120.3(7) . . ?
O51 N21 O52 120.1(7) . . ?
O53 N21 O52 119.5(6) . . ?
O15 C63 C64 112.6(7) . . ?
O40 C61 C60 115.3(7) . . ?
O8 Zn1 O7 88.91(16) . . ?
O8 Zn1 N5 83.32(17) . . ?
O7 Zn1 N5 104.67(17) . . ?
O8 Zn1 N7 103.31(16) . . ?
O7 Zn1 N7 82.23(16) . . ?
N5 Zn1 N7 170.68(18) . . ?
O8 Zn1 O4 89.72(16) . . ?
O7 Zn1 O4 157.62(15) . . ?
N5 Zn1 O4 97.34(17) . . ?
N7 Zn1 O4 76.37(16) . . ?
O8 Zn1 O3 159.35(16) . . ?
O7 Zn1 O3 92.93(17) . . ?
N5 Zn1 O3 76.31(17) . . ?
N7 Zn1 O3 97.32(16) . . ?
O4 Zn1 O3 96.16(17) . . ?
O6 Zn2 N1 103.92(18) . . ?
O6 Zn2 O5 89.83(16) . . ?
N1 Zn2 O5 82.70(17) . . ?
O6 Zn2 O1 94.23(18) . . ?
N1 Zn2 O1 76.68(18) . . ?
O5 Zn2 O1 159.35(17) . . ?
O6 Zn2 N3 83.21(18) . . ?
N1 Zn2 N3 171.49(19) . . ?
O5 Zn2 N3 102.20(17) . . ?
O1 Zn2 N3 98.39(17) . . ?
O6 Zn2 O2 157.85(18) . . ?
N1 Zn2 O2 98.07(19) . . ?
O5 Zn2 O2 90.33(17) . . ?
O1 Zn2 O2 93.38(17) . . ?
N3 Zn2 O2 75.11(19) . . ?
C16 O6 Zn2 132.1(4) . . ?
C25 O3 Zn1 113.9(4) . . ?
C17 O4 Zn1 113.9(4) . . ?
C28 O8 Zn1 132.0(4) . . ?
C9 O2 Zn2 113.0(4) . . ?
C1 O1 Zn2 113.8(4) . . ?
C24 O7 Zn1 132.5(3) . . ?
C7 O5 Zn2 132.9(3) . . ?
C18 N7 N8 116.2(4) . . ?
C18 N7 Zn1 132.2(4) . . ?
N8 N7 Zn1 111.5(3) . . ?
C26 N5 N6 116.9(5) . . ?
C26 N5 Zn1 131.4(4) . . ?
N6 N5 Zn1 111.6(3) . . ?
C10 N3 N4 117.6(5) . . ?
C10 N3 Zn2 130.5(4) . . ?
N4 N3 Zn2 111.9(4) . . ?
C17 N8 N7 116.7(4) . . ?
C2 N1 N2 116.1(5) . . ?
C2 N1 Zn2 132.4(4) . . ?
N2 N1 Zn2 111.5(4) . . ?
N7 C18 C19 123.8(5) . . ?
C20 C19 C24 118.2(5) . . ?
C20 C19 C18 116.8(5) . . ?
C24 C19 C18 124.9(5) . . ?
C32 C31 C30 119.8(6) . . ?
C22 C23 C24 121.1(6) . . ?
O4 C17 N8 121.0(5) . . ?
O4 C17 C40 122.9(5) . . ?
N8 C17 C40 116.0(5) . . ?
C20 C21 C22 118.4(5) . . ?
N5 C26 C27 124.4(5) . . ?
N1 C2 C3 124.2(6) . . ?
C25 N6 N5 116.6(5) . . ?
C30 C29 C28 121.4(6) . . ?
C1 N2 N1 115.4(5) . . ?
C5 C8 C4 118.8(6) . . ?
C5 C6 C7 121.4(5) . . ?
C14 C15 C16 122.0(6) . . ?
C28 C27 C32 119.1(5) . . ?
C28 C27 C26 124.4(5) . . ?
C32 C27 C26 116.5(5) . . ?
C9 N4 N3 116.7(5) . . ?
C12 C13 C14 118.9(6) . . ?
O8 C28 C27 122.2(5) . . ?
O8 C28 C29 119.4(5) . . ?
C27 C28 C29 118.4(5) . . ?
O7 C24 C23 118.9(5) . . ?
O7 C24 C19 121.6(5) . . ?
C23 C24 C19 119.6(5) . . ?
C16 C11 C12 117.2(6) . . ?
C16 C11 C10 124.4(6) . . ?
C12 C11 C10 118.1(5) . . ?
O5 C7 C6 120.6(5) . . ?
O5 C7 C3 121.3(5) . . ?
C6 C7 C3 118.1(5) . . ?
O2 C9 N4 121.7(6) . . ?
O2 C9 C35 121.2(6) . . ?
N4 C9 C35 117.1(6) . . ?
C6 C5 C8 120.9(6) . . ?
O3 C25 N6 121.3(6) . . ?
O3 C25 C48 122.0(6) . . ?
N6 C25 C48 116.6(6) . . ?
C31 C32 C27 121.2(6) . . ?
C21 C20 C19 122.0(5) . . ?
O6 C16 C15 119.7(5) . . ?
O6 C16 C11 121.4(5) . . ?
C15 C16 C11 118.9(5) . . ?
C4 C3 C7 119.3(5) . . ?
C4 C3 C2 116.6(5) . . ?
C7 C3 C2 124.1(5) . . ?
O1 C1 N2 122.3(6) . . ?
O1 C1 C45 123.7(6) . . ?
N2 C1 C45 113.9(6) . . ?
N3 C10 C11 125.2(5) . . ?
C29 C30 C31 120.0(6) . . ?
C13 C12 C11 123.0(6) . . ?
C8 C4 C3 121.5(6) . . ?
C23 C22 C21 120.7(6) . . ?
C15 C14 C13 120.0(6) . . ?
C42 C41 C40 114.2(5) . . ?
C17 C40 C41 111.1(5) . . ?
C41 C42 C43 111.5(6) . . ?
C9 C35 C36 112.0(6) . . ?
C1 C45 C46 110.1(6) . . ?
C44 C43 C42 114.7(7) . . ?
C39 C38 C37 112.4(6) . . ?
O10 C39 C38 109.7(6) . . ?
O11 C44 C43 113.0(8) . . ?
C50 C49 C48 114.1(7) . . ?
C47 C46 C45 114.2(7) . . ?
C37 C36 C35 113.0(6) . . ?
C38 C37 C36 113.0(6) . . ?
C25 C48 C49 109.7(7) . . ?
C46 C47 C53 114.0(7) . . ?
C52 C51 C50 114.8(8) . . ?
C49 C50 C51 113.5(8) . . ?
C47 C53 C54 113.9(7) . . ?
O12 C52 C51 109.9(8) . . ?
O13 C54 C53 112.3(8) . . ?
O55 N20 O54 121.8(6) . . ?
O55 N20 O56 120.8(6) . . ?
O54 N20 O56 117.2(6) . . ?

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
O15 H15 O56 0.84 2.09 2.772(7) 137.5 2_666
C60 H60C O52 0.98 2.62 3.352(11) 131.7 .
O40 H40 O52 0.84 2.02 2.779(7) 149.2 .
O6 H601 O7 0.77(6) 1.66(6) 2.433(5) 177(8) 1_455
N8 H801 O15 1.04(7) 1.73(7) 2.754(6) 169(6) 2_655
C18 H18 O3 0.95 2.63 3.413(6) 140.3 2_755
C26 H26 O54 0.95 2.56 3.339(7) 139.5 1_554
C2 H2 O53 0.95 2.56 3.342(8) 139.4 .
C2 H2 O12 0.95 2.63 3.501(8) 152.9 2_655
N6 H61 O54 0.81(8) 1.98(8) 2.776(7) 167(7) 1_554
N2 H30 O53 0.80(8) 1.95(8) 2.751(8) 175(8) .
N4 H41 O40 0.94(8) 1.86(8) 2.787(7) 169(7) 1_455
C10 H10 O1 0.95 2.51 3.278(7) 138.4 2_566
O10 H10A O2 0.84 1.96 2.756(7) 156.8 2_556
O11 H11 O4 0.84 2.03 2.804(8) 151.9 2_655
C45 H45B O52 0.99 2.53 3.467(10) 157.6 .
O12 H12A O53 0.84 2.13 2.857(9) 145.3 2_655
O13 H990 O56 0.84 2.26 3.094(11) 171.9 .
O8 H7 O5 0.78(6) 1.66(6) 2.426(6) 168(9) 1_655

_refine_diff_density_max         3.364
_refine_diff_density_min         -1.322
_refine_diff_density_rms         0.140

_shelxl_version_number           2013-4



# start Validation Reply Form
_vrf_PLAT097_Zn1                 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.36 eA-3  
RESPONSE: A large number of reflections show a large number of disagreeable 
values of error/esd with Fo2 bigger that Fc2. Both findings suggest are
likely a signal of non-merohedral twining but the searching of additional
domains were unsucessful. This is likely yielding and some residual density
around the heavier atoms.
;
_vrf_PLAT230_Zn1                 
;
PROBLEM: Hirshfeld Test Diff for   C48      --C49       .        7.5 s.u.  
RESPONSE: Related with some dissorder of this terminal group but it is not
with the nature of the atoms.
;
_vrf_PLAT417_Zn1                 
;
PROBLEM: Short Inter D-H..H-D       H15      ..H801             1.93 Ang.  
RESPONSE: There is a rather strong H-bonding interactions between the 
N8-H201 group (as donor group) anf the  oxygen atom of the ethanolic 
O15(H15) group.
;
_vrf_PLAT780_Zn1                 
;
PROBLEM: Coordinates do not Form a Properly Connected Set     Please Do ! 
RESPONSE: ...
;
_vrf_PLAT971_Zn1                 
;
PROBLEM: Check Calcd Resid. Dens.  0.91A   From Zn2             3.33 eA-3  
RESPONSE:  A large number of reflections show a large number of disagreeable 
values of error/esd with Fo2 bigger that Fc2. Both findings suggest are
likely a signal of non-merohedral twining but the searching of additional
domains were unsucessful. This is likely yielding and some residual density
around the heavier atoms.
;
####################################################################### 
# 
# 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_Cu2b
_database_code_depnum_ccdc_archive 'CCDC 1858830'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2018-07-27 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H32 Cu2 F6 N4 O6 Si'
_chemical_formula_weight         765.72

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'
Si Si 0.2541 0.3302 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

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

_cell_length_a                   15.2574(3)
_cell_length_b                   7.15810(10)
_cell_length_c                   13.6618(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.2698(6)
_cell_angle_gamma                90
_cell_volume                     1457.98(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5544
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      66.64

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    2.987
_shelx_estimated_absorpt_T_min   0.783
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5624
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker CCD Smart 6000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8288
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.310
_diffrn_reflns_theta_max         66.636
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             1389
_reflns_number_gt                1288
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+2.4371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1389
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.1211(3) 0.0000 0.2716(3) 0.169(4) Uani 1 2 d S T P . .
H3 H 0.0934 0.0745 0.2309 0.253 Uiso 0.5 1 calc R U P . .
C11 C 0.1599(3) 0.0000 0.4472(3) 0.0627(13) Uani 1 2 d S T P . .
H11A H 0.1972 0.1094 0.4461 0.075 Uiso 0.5 1 calc R U P . .
H11B H 0.1972 -0.1094 0.4461 0.075 Uiso 0.5 1 calc R U P . .
C12 C 0.0867(3) 0.0000 0.3544(3) 0.0688(15) Uani 1 2 d S T P . .
H12 H 0.0257 0.0000 0.3542 0.083 Uiso 1 2 calc R U P . .
C13 C 0.3878(3) 0.0000 1.3526(3) 0.0454(9) Uani 1 2 d S T P . .
H13 H 0.3694 0.0000 1.4132 0.054 Uiso 1 2 calc R U P . .
Cu1 Cu 0.40550(3) 0.0000 0.94871(3) 0.0312(2) Uani 1 2 d S T P . .
O1 O 0.47522(14) 0.0000 1.08407(16) 0.0299(5) Uani 1 2 d S T P . .
O2 O 0.32174(15) 0.0000 0.81841(17) 0.0419(6) Uani 1 2 d S T P . .
N1 N 0.29311(17) 0.0000 0.9941(2) 0.0303(6) Uani 1 2 d S T P . .
C7 C 0.2409(2) 0.0000 0.8242(2) 0.0314(7) Uani 1 2 d S T P . .
C6 C 0.2808(2) 0.0000 1.0838(2) 0.0335(7) Uani 1 2 d S T P . .
H1 H 0.2223 0.0000 1.0933 0.040 Uiso 1 2 calc R U P . .
N2 N 0.22030(18) 0.0000 0.9134(2) 0.0354(7) Uani 1 2 d S T P . .
H6 H 0.1658 0.0000 0.9210 0.042 Uiso 1 2 calc R U P . .
C1 C 0.4455(2) 0.0000 1.1692(2) 0.0299(7) Uani 1 2 d S T P . .
C9 C 0.2013(2) 0.0000 0.6366(3) 0.0431(9) Uani 1 2 d S T P . .
H9A H 0.2386 -0.1095 0.6356 0.052 Uiso 0.5 1 calc R U P . .
H9B H 0.2386 0.1095 0.6356 0.052 Uiso 0.5 1 calc R U P . .
C5 C 0.5063(2) 0.0000 1.2609(3) 0.0466(10) Uani 1 2 d S T P . .
H5 H 0.5674 0.0000 1.2619 0.056 Uiso 1 2 calc R U P . .
C8 C 0.1668(2) 0.0000 0.7327(3) 0.0366(8) Uani 1 2 d S T P . .
H8A H 0.1296 0.1095 0.7339 0.044 Uiso 0.5 1 calc R U P . .
H8B H 0.1296 -0.1095 0.7339 0.044 Uiso 0.5 1 calc R U P . .
C3 C 0.3265(2) 0.0000 1.2637(3) 0.0397(8) Uani 1 2 d S T P . .
H3A H 0.2657 0.0000 1.2645 0.048 Uiso 1 2 calc R U P . .
C4 C 0.4783(3) 0.0000 1.3503(3) 0.0504(10) Uani 1 2 d S T P . .
H4 H 0.5207 0.0000 1.4102 0.061 Uiso 1 2 calc R U P . .
C2 C 0.3528(2) 0.0000 1.1705(2) 0.0322(7) Uani 1 2 d S T P . .
C10 C 0.1268(2) 0.0000 0.5434(3) 0.0439(9) Uani 1 2 d S T P . .
H10A H 0.0895 -0.1094 0.5447 0.053 Uiso 0.5 1 calc R U P . .
H10B H 0.0895 0.1094 0.5447 0.053 Uiso 0.5 1 calc R U P . .
Si1 Si 0.5000 0.5000 1.0000 0.0284(3) Uani 1 4 d S T P . .
F1 F 0.42220(9) 0.3362(2) 0.95606(11) 0.0437(4) Uani 1 1 d . . . . .
F2 F 0.53407(14) 0.5000 0.89096(15) 0.0537(6) Uani 1 2 d S T 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
O3 C12 1.345(6) . ?
C11 C12 1.501(5) . ?
C11 C10 1.505(5) . ?
C13 C3 1.367(5) . ?
C13 C4 1.386(6) . ?
Cu1 O1 1.927(2) . ?
Cu1 N1 1.943(3) . ?
Cu1 O2 1.958(2) . ?
Cu1 O1 1.964(2) 5_657 ?
Cu1 Cu1 2.9261(8) 5_657 ?
O1 C1 1.335(4) . ?
O1 Cu1 1.964(2) 5_657 ?
O2 C7 1.253(4) . ?
N1 C6 1.278(4) . ?
N1 N2 1.389(4) . ?
C7 N2 1.321(4) . ?
C7 C8 1.497(4) . ?
C6 C2 1.435(5) . ?
C1 C5 1.391(5) . ?
C1 C2 1.419(5) . ?
C9 C8 1.515(5) . ?
C9 C10 1.517(5) . ?
C5 C4 1.377(5) . ?
C3 C2 1.414(5) . ?
Si1 F2 1.679(2) . ?
Si1 F2 1.679(2) 5_667 ?
Si1 F1 1.6854(14) . ?
Si1 F1 1.6855(14) 5_667 ?
Si1 F1 1.6855(13) 2_657 ?
Si1 F1 1.6855(13) 6_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C10 114.2(4) . . ?
O3 C12 C11 110.9(4) . . ?
C3 C13 C4 118.5(3) . . ?
O1 Cu1 N1 92.21(10) . . ?
O1 Cu1 O2 173.02(9) . . ?
N1 Cu1 O2 80.81(10) . . ?
O1 Cu1 O1 82.50(9) . 5_657 ?
N1 Cu1 O1 174.71(10) . 5_657 ?
O2 Cu1 O1 104.47(9) . 5_657 ?
O1 Cu1 Cu1 41.73(6) . 5_657 ?
N1 Cu1 Cu1 133.94(8) . 5_657 ?
O2 Cu1 Cu1 145.25(7) . 5_657 ?
O1 Cu1 Cu1 40.77(6) 5_657 5_657 ?
C1 O1 Cu1 128.0(2) . . ?
C1 O1 Cu1 134.5(2) . 5_657 ?
Cu1 O1 Cu1 97.50(9) . 5_657 ?
C7 O2 Cu1 113.8(2) . . ?
C6 N1 N2 120.3(3) . . ?
C6 N1 Cu1 128.7(2) . . ?
N2 N1 Cu1 111.0(2) . . ?
O2 C7 N2 119.2(3) . . ?
O2 C7 C8 121.8(3) . . ?
N2 C7 C8 119.0(3) . . ?
N1 C6 C2 123.3(3) . . ?
C7 N2 N1 115.2(3) . . ?
O1 C1 C5 120.0(3) . . ?
O1 C1 C2 122.4(3) . . ?
C5 C1 C2 117.6(3) . . ?
C8 C9 C10 113.0(3) . . ?
C4 C5 C1 121.7(3) . . ?
C7 C8 C9 112.5(3) . . ?
C13 C3 C2 121.8(3) . . ?
C5 C4 C13 121.2(3) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 C6 115.4(3) . . ?
C1 C2 C6 125.4(3) . . ?
C11 C10 C9 113.7(3) . . ?
F2 Si1 F2 180.00(13) . 5_667 ?
F2 Si1 F1 90.66(7) . . ?
F2 Si1 F1 89.34(7) 5_667 . ?
F2 Si1 F1 89.34(7) . 5_667 ?
F2 Si1 F1 90.66(7) 5_667 5_667 ?
F1 Si1 F1 180.0 . 5_667 ?
F2 Si1 F1 89.34(7) . 2_657 ?
F2 Si1 F1 90.66(7) 5_667 2_657 ?
F1 Si1 F1 91.86(9) . 2_657 ?
F1 Si1 F1 88.13(9) 5_667 2_657 ?
F2 Si1 F1 90.66(7) . 6_565 ?
F2 Si1 F1 89.34(7) 5_667 6_565 ?
F1 Si1 F1 88.14(9) . 6_565 ?
F1 Si1 F1 91.87(9) 5_667 6_565 ?
F1 Si1 F1 180.0 2_657 6_565 ?

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
C6 H1 F1 0.93 2.46 3.248(3) 142.5 4_547
C6 H1 F1 0.93 2.46 3.248(3) 142.5 7_557
C5 H5 O2 0.93 2.20 3.044(4) 150.1 5_657
N2 H6 F2 0.86 1.96 2.792(3) 161.5 3_445
N2 H6 F1 0.86 2.64 3.306(3) 135.5 4_547
N2 H6 F1 0.86 2.64 3.306(3) 135.5 7_557
O3 H3 F2 0.82 2.34 2.882(4) 124.5 7_556
O3 H3 F1 0.82 2.59 3.258(4) 139.0 7_556
C6 H1 F1 0.93 2.46 3.248(3) 142.5 4_547
C6 H1 F1 0.93 2.46 3.248(3) 142.5 7_557
C5 H5 O2 0.93 2.20 3.044(4) 150.1 5_657
N2 H6 F2 0.86 1.96 2.792(3) 161.5 3_445
N2 H6 F1 0.86 2.64 3.306(3) 135.5 4_547
N2 H6 F1 0.86 2.64 3.306(3) 135.5 7_557
O3 H3 F2 0.82 2.34 2.882(4) 124.5 7_556
O3 H3 F1 0.82 2.59 3.258(4) 139.0 7_556
C6 H1 F1 0.93 2.46 3.248(3) 142.5 4_547
C6 H1 F1 0.93 2.46 3.248(3) 142.5 7_557
C5 H5 O2 0.93 2.20 3.044(4) 150.1 5_657
N2 H6 F2 0.86 1.96 2.792(3) 161.5 3_445
N2 H6 F1 0.86 2.64 3.306(3) 135.5 4_547
N2 H6 F1 0.86 2.64 3.306(3) 135.5 7_557
O3 H3 F2 0.82 2.34 2.882(4) 124.5 7_556
O3 H3 F1 0.82 2.59 3.258(4) 139.0 7_556

_refine_diff_density_max         0.449
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ni2
_database_code_depnum_ccdc_archive 'CCDC 1858831'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2018-07-27 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H25 N3 Ni O8'
_chemical_formula_weight         434.09

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4517(14)
_cell_length_b                   10.1415(14)
_cell_length_c                   10.5338(15)
_cell_angle_alpha                107.386(7)
_cell_angle_beta                 91.631(8)
_cell_angle_gamma                92.042(8)
_cell_volume                     962.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8059
_cell_measurement_theta_min      4.40
_cell_measurement_theta_max      68.07

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.887
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3734
_exptl_absorpt_correction_T_max  0.7374
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker CCD Smart 6000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15387
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.402
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             3362
_reflns_number_gt                2245
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1926P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3362
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.2785
_refine_ls_wR_factor_gt          0.2411
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H4WA H 0.458(7) 0.884(7) -0.297(7) 0.05(2) Uiso 1 1 d . . . . .
H4WB H 0.542(9) 0.966(9) -0.294(8) 0.09(3) Uiso 1 1 d . . . . .
H1 H 0.890(7) 0.902(6) 0.300(6) 0.057(17) Uiso 1 1 d . . . . .
Ni1 Ni 0.42147(9) 1.06240(9) -0.09620(9) 0.0485(4) Uani 1 1 d . . . . .
O1 O 0.6134(4) 1.0808(4) 0.0013(4) 0.0517(10) Uani 1 1 d . . . . .
O2 O 0.5869(4) 0.7969(5) 0.2050(4) 0.0620(11) Uani 1 1 d . . . . .
O3 O 0.3510(5) 1.2106(5) 0.0781(5) 0.0624(12) Uani 1 1 d . . . . .
O4 O 0.5120(6) 0.9152(6) -0.2571(5) 0.0590(12) Uani 1 1 d . . . . .
N1 N 0.7739(5) 0.9754(5) 0.1765(5) 0.0490(11) Uani 1 1 d . . . . .
N2 N 0.8022(6) 0.8972(6) 0.2609(5) 0.0578(13) Uani 1 1 d . . . . .
C1 C 0.7324(6) 1.1516(6) -0.0027(5) 0.0449(12) Uani 1 1 d . . . . .
C2 C 0.7365(6) 1.2432(6) -0.0792(6) 0.0553(14) Uani 1 1 d . . . . .
H2 H 0.6554 1.2533 -0.1268 0.066 Uiso 1 1 calc R U . . .
C3 C 0.8588(7) 1.3185(7) -0.0847(7) 0.0660(17) Uani 1 1 d . . . . .
H3 H 0.8584 1.3785 -0.1364 0.079 Uiso 1 1 calc R U . . .
C4 C 0.9831(7) 1.3075(7) -0.0152(7) 0.0682(18) Uani 1 1 d . . . . .
H4A H 1.0651 1.3592 -0.0192 0.082 Uiso 1 1 calc R U . . .
C5 C 0.9799(7) 1.2171(7) 0.0597(7) 0.0621(16) Uani 1 1 d . . . . .
H5 H 1.0622 1.2076 0.1061 0.075 Uiso 1 1 calc R U . . .
C6 C 0.8589(6) 1.1398(6) 0.0685(6) 0.0483(13) Uani 1 1 d . . . . .
C7 C 0.8729(6) 1.0521(6) 0.1534(6) 0.0539(14) Uani 1 1 d . . . . .
H7 H 0.9614 1.0518 0.1943 0.065 Uiso 1 1 calc R U . . .
C8 C 0.6996(7) 0.8072(6) 0.2703(6) 0.0550(14) Uani 1 1 d . . . . .
O10 O 0.6925(5) 0.0391(6) 0.6042(5) 0.0787(15) Uani 1 1 d . . . . .
O5 O 0.6633(6) 0.2265(6) 0.4626(6) 0.0904(17) Uani 1 1 d . . . . .
H5A H 0.6844 0.1685 0.4989 0.136 Uiso 1 1 calc R U . . .
O11 O 0.9169(6) 0.0961(7) 0.6165(5) 0.0857(16) Uani 1 1 d . . . . .
N10 N 0.8184(6) 0.0222(6) 0.6353(5) 0.0672(15) Uani 1 1 d . . . . .
O12 O 0.8355(7) -0.0728(7) 0.6861(7) 0.105(2) Uani 1 1 d . . . . .
C9 C 0.7307(8) 0.7189(8) 0.3565(7) 0.074(2) Uani 1 1 d . . . . .
H9A H 0.6421 0.6864 0.3835 0.089 Uiso 1 1 calc R U . . .
H9B H 0.7832 0.7742 0.4362 0.089 Uiso 1 1 calc R U . . .
C13 C 0.7813(8) 0.3069(8) 0.4576(7) 0.075(2) Uani 1 1 d . . . . .
H13A H 0.8555 0.2491 0.4126 0.090 Uiso 1 1 calc R U . . .
H13B H 0.8163 0.3572 0.5471 0.090 Uiso 1 1 calc R U . . .
C10 C 0.8157(12) 0.5949(9) 0.2878(9) 0.100(3) Uani 1 1 d . . . . .
H10A H 0.9032 0.6281 0.2595 0.120 Uiso 1 1 calc R U . . .
H10B H 0.7624 0.5400 0.2085 0.120 Uiso 1 1 calc R U . . .
C11 C 0.8522(11) 0.5012(10) 0.3731(10) 0.106(3) Uani 1 1 d . . . . .
H11A H 0.9330 0.4485 0.3364 0.128 Uiso 1 1 calc R U . . .
H11B H 0.8803 0.5589 0.4622 0.128 Uiso 1 1 calc R U . . .
C12 C 0.7416(10) 0.4084(9) 0.3821(8) 0.090(3) Uani 1 1 d . . . . .
H12A H 0.7082 0.3561 0.2927 0.108 Uiso 1 1 calc R U . . .
H12B H 0.6637 0.4613 0.4257 0.108 Uiso 1 1 calc R U . . .
C20 C 0.3984(9) 1.3535(8) 0.1166(8) 0.083(2) Uani 1 1 d . . . . .
H20A H 0.3672 1.3940 0.0487 0.100 Uiso 1 1 calc R U . . .
H20B H 0.5012 1.3596 0.1219 0.100 Uiso 1 1 calc R U . . .
C21 C 0.3457(11) 1.4324(11) 0.2438(10) 0.112(3) Uani 1 1 d . . . . .
H21A H 0.2448 1.4178 0.2428 0.169 Uiso 1 1 calc R U . . .
H21B H 0.3690 1.5289 0.2591 0.169 Uiso 1 1 calc R U . . .
H21C H 0.3887 1.4025 0.3136 0.169 Uiso 1 1 calc R U . . .
H101 H 0.350(8) 1.170(8) 0.121(8) 0.07(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 1.985(5) 2_675 ?
Ni1 O1 2.017(4) 2_675 ?
Ni1 O1 2.034(4) . ?
Ni1 O2 2.082(4) 2_675 ?
Ni1 O4 2.120(5) . ?
Ni1 O3 2.137(5) . ?
O1 C1 1.321(6) . ?
O1 Ni1 2.017(4) 2_675 ?
O2 C8 1.236(7) . ?
O2 Ni1 2.082(4) 2_675 ?
O3 C20 1.434(9) . ?
N1 C7 1.271(7) . ?
N1 N2 1.384(6) . ?
N1 Ni1 1.985(5) 2_675 ?
N2 C8 1.334(8) . ?
C1 C2 1.400(8) . ?
C1 C6 1.421(7) . ?
C2 C3 1.374(8) . ?
C3 C4 1.392(9) . ?
C4 C5 1.377(9) . ?
C5 C6 1.385(8) . ?
C6 C7 1.443(8) . ?
C8 C9 1.484(8) . ?
O10 N10 1.257(7) . ?
O5 C13 1.370(9) . ?
O11 N10 1.231(7) . ?
N10 O12 1.247(8) . ?
C9 C10 1.520(11) . ?
C13 C12 1.527(9) . ?
C10 C11 1.532(10) . ?
C11 C12 1.405(12) . ?
C20 C21 1.452(11) . ?

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
N1 Ni1 O1 89.82(17) 2_675 2_675 ?
N1 Ni1 O1 171.37(17) 2_675 . ?
O1 Ni1 O1 81.58(17) 2_675 . ?
N1 Ni1 O2 78.45(17) 2_675 2_675 ?
O1 Ni1 O2 168.17(16) 2_675 2_675 ?
O1 Ni1 O2 110.13(17) . 2_675 ?
N1 Ni1 O4 94.1(2) 2_675 . ?
O1 Ni1 O4 91.49(18) 2_675 . ?
O1 Ni1 O4 86.81(19) . . ?
O2 Ni1 O4 90.88(19) 2_675 . ?
N1 Ni1 O3 91.89(19) 2_675 . ?
O1 Ni1 O3 86.82(19) 2_675 . ?
O1 Ni1 O3 87.02(17) . . ?
O2 Ni1 O3 91.99(19) 2_675 . ?
O4 Ni1 O3 173.78(19) . . ?
C1 O1 Ni1 128.4(3) . 2_675 ?
C1 O1 Ni1 132.9(3) . . ?
Ni1 O1 Ni1 98.42(16) 2_675 . ?
C8 O2 Ni1 112.8(4) . 2_675 ?
C20 O3 Ni1 122.4(5) . . ?
C7 N1 N2 118.9(5) . . ?
C7 N1 Ni1 128.7(4) . 2_675 ?
N2 N1 Ni1 112.2(4) . 2_675 ?
C8 N2 N1 116.5(5) . . ?
O1 C1 C2 119.7(5) . . ?
O1 C1 C6 122.7(5) . . ?
C2 C1 C6 117.5(5) . . ?
C3 C2 C1 120.9(5) . . ?
C2 C3 C4 121.9(6) . . ?
C5 C4 C3 117.5(6) . . ?
C4 C5 C6 122.5(6) . . ?
C5 C6 C1 119.7(5) . . ?
C5 C6 C7 115.4(5) . . ?
C1 C6 C7 124.9(5) . . ?
N1 C7 C6 125.1(5) . . ?
O2 C8 N2 119.9(5) . . ?
O2 C8 C9 123.0(6) . . ?
N2 C8 C9 117.0(5) . . ?
O11 N10 O12 123.2(6) . . ?
O11 N10 O10 121.3(6) . . ?
O12 N10 O10 115.5(6) . . ?
C8 C9 C10 112.9(6) . . ?
O5 C13 C12 108.6(6) . . ?
C9 C10 C11 115.0(7) . . ?
C12 C11 C10 114.7(8) . . ?
C11 C12 C13 114.8(7) . . ?
O3 C20 C21 112.7(8) . . ?

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
C7 N1 N2 C8 -172.8(6) . . . . ?
Ni1 N1 N2 C8 2.8(7) 2_675 . . . ?
Ni1 O1 C1 C2 177.5(4) 2_675 . . . ?
Ni1 O1 C1 C2 5.4(8) . . . . ?
Ni1 O1 C1 C6 -2.9(8) 2_675 . . . ?
Ni1 O1 C1 C6 -174.9(4) . . . . ?
O1 C1 C2 C3 179.8(6) . . . . ?
C6 C1 C2 C3 0.1(9) . . . . ?
C1 C2 C3 C4 -0.1(11) . . . . ?
C2 C3 C4 C5 0.4(11) . . . . ?
C3 C4 C5 C6 -0.6(11) . . . . ?
C4 C5 C6 C1 0.7(10) . . . . ?
C4 C5 C6 C7 -178.8(6) . . . . ?
O1 C1 C6 C5 180.0(5) . . . . ?
C2 C1 C6 C5 -0.4(9) . . . . ?
O1 C1 C6 C7 -0.6(10) . . . . ?
C2 C1 C6 C7 179.1(5) . . . . ?
N2 N1 C7 C6 -179.6(5) . . . . ?
Ni1 N1 C7 C6 5.7(9) 2_675 . . . ?
C5 C6 C7 N1 178.6(6) . . . . ?
C1 C6 C7 N1 -0.8(10) . . . . ?
Ni1 O2 C8 N2 -3.0(8) 2_675 . . . ?
Ni1 O2 C8 C9 179.6(5) 2_675 . . . ?
N1 N2 C8 O2 0.2(9) . . . . ?
N1 N2 C8 C9 177.8(5) . . . . ?
O2 C8 C9 C10 96.4(9) . . . . ?
N2 C8 C9 C10 -81.0(8) . . . . ?
C8 C9 C10 C11 179.3(7) . . . . ?
C9 C10 C11 C12 79.7(11) . . . . ?
C10 C11 C12 C13 175.2(7) . . . . ?
O5 C13 C12 C11 178.0(8) . . . . ?
Ni1 O3 C20 C21 -175.3(5) . . . . ?

_refine_diff_density_max         0.951
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.135

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Cu2a
_database_code_depnum_ccdc_archive 'CCDC 1858829'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2018-07-27 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H34 Cu2 N6 O12'
_chemical_formula_weight         749.67

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'
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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.8828(4)
_cell_length_b                   7.2916(2)
_cell_length_c                   17.5807(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.6591(6)
_cell_angle_gamma                90
_cell_volume                     1521.63(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      3.72
_cell_measurement_theta_max      68.29

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    2.364
_shelx_estimated_absorpt_T_min   0.633
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker CCD Smart 6000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17607
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.724
_diffrn_reflns_theta_max         68.276
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2766
_reflns_number_gt                2701
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.5660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2766
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.83050(19) 0.6798(3) 0.37996(12) 0.0944(7) Uani 1 1 d . . . . .
O5 O 0.71175(16) 0.4586(3) 0.36950(9) 0.0682(5) Uani 1 1 d . . . . .
N4 N 0.76081(14) 0.5784(2) 0.40704(10) 0.0432(4) Uani 1 1 d . . . . .
Cu1 Cu 0.60940(2) 0.41826(3) 0.52834(2) 0.03302(12) Uani 1 1 d . . . . .
O2 O 0.72004(12) 0.41258(17) 0.61726(8) 0.0456(3) Uani 1 1 d . . . . .
O3 O 1.12371(11) 0.31755(19) 0.93565(8) 0.0474(3) Uani 1 1 d . . . . .
H3 H 1.1672 0.2488 0.9594 0.071 Uiso 1 1 calc R U . . .
O1 O 0.51285(9) 0.63116(17) 0.54572(7) 0.0362(3) Uani 1 1 d . . . . .
N1 N 0.67582(11) 0.18053(19) 0.51192(8) 0.0322(3) Uani 1 1 d . . . . .
O4 O 0.73784(14) 0.5983(2) 0.47551(9) 0.0608(4) Uani 1 1 d . . . . .
C5 C 0.55422(15) 0.0781(2) 0.40785(10) 0.0356(4) Uani 1 1 d . . . . .
N2 N 0.76615(12) 0.1480(2) 0.56261(8) 0.0363(3) Uani 1 1 d . . . . .
H2 H 0.8084 0.0527 0.5597 0.044 Uiso 1 1 calc R U . . .
C8 C 0.64851(15) 0.0596(2) 0.46165(10) 0.0368(4) Uani 1 1 d . . . . .
H8 H 0.6921 -0.0461 0.4598 0.044 Uiso 1 1 calc R U . . .
C6 C 0.53851(17) -0.0660(3) 0.35475(12) 0.0474(5) Uani 1 1 d . . . . .
H6A H 0.5893 -0.1631 0.3559 0.057 Uiso 1 1 calc R U . . .
C2 C 0.52288(13) 0.7745(2) 0.59394(9) 0.0318(3) Uani 1 1 d . . . . .
C4 C 0.62552(17) 0.9234(3) 0.69885(11) 0.0450(5) Uani 1 1 d . . . . .
H4 H 0.6859 0.9229 0.7344 0.054 Uiso 1 1 calc R U . . .
C13 C 1.01056(16) 0.2662(3) 0.94903(11) 0.0464(4) Uani 1 1 d . . . . .
H13A H 0.9903 0.3110 0.9985 0.056 Uiso 1 1 calc R U . . .
H13B H 1.0043 0.1336 0.9491 0.056 Uiso 1 1 calc R U . . .
C3 C 0.61348(15) 0.7810(3) 0.64753(10) 0.0409(4) Uani 1 1 d . . . . .
H3A H 0.6667 0.6874 0.6486 0.049 Uiso 1 1 calc R U . . .
C1 C 0.78275(14) 0.2757(2) 0.61629(10) 0.0376(4) Uani 1 1 d . . . . .
C9 C 0.87804(16) 0.2467(3) 0.67327(10) 0.0449(4) Uani 1 1 d . . . . .
H9A H 0.9458 0.2997 0.6537 0.054 Uiso 1 1 calc R U . . .
H9B H 0.8907 0.1160 0.6794 0.054 Uiso 1 1 calc R U . . .
C7 C 0.45046(18) -0.0667(3) 0.30158(12) 0.0509(5) Uani 1 1 d . . . . .
H7 H 0.4420 -0.1618 0.2665 0.061 Uiso 1 1 calc R U . . .
C11 C 0.94977(15) 0.2704(3) 0.80921(10) 0.0404(4) Uani 1 1 d . . . . .
H11A H 0.9517 0.1375 0.8114 0.048 Uiso 1 1 calc R U . . .
H11B H 1.0223 0.3122 0.7929 0.048 Uiso 1 1 calc R U . . .
C10 C 0.85848(15) 0.3300(3) 0.75071(10) 0.0413(4) Uani 1 1 d . . . . .
H10A H 0.7854 0.2918 0.7674 0.050 Uiso 1 1 calc R U . . .
H10B H 0.8583 0.4627 0.7467 0.050 Uiso 1 1 calc R U . . .
C12 C 0.93119(15) 0.3449(3) 0.88817(10) 0.0431(4) Uani 1 1 d . . . . .
H12A H 0.9401 0.4771 0.8874 0.052 Uiso 1 1 calc R U . . .
H12B H 0.8544 0.3187 0.9011 0.052 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 N4 1.223(2) . ?
O5 N4 1.225(2) . ?
N4 O4 1.255(2) . ?
Cu1 N1 1.9319(14) . ?
Cu1 O1 1.9390(11) 3_666 ?
Cu1 O1 1.9627(12) . ?
Cu1 O2 1.9959(13) . ?
Cu1 O4 2.2465(15) . ?
Cu1 Cu1 2.9889(4) 3_666 ?
O2 C1 1.246(2) . ?
O3 C13 1.426(2) . ?
O1 C2 1.3475(19) . ?
O1 Cu1 1.9391(11) 3_666 ?
N1 C8 1.279(2) . ?
N1 N2 1.3835(19) . ?
C5 C6 1.412(2) . ?
C5 C2 1.412(2) 3_666 ?
C5 C8 1.439(2) . ?
N2 C1 1.334(2) . ?
C6 C7 1.370(3) . ?
C2 C3 1.398(2) . ?
C2 C5 1.412(2) 3_666 ?
C4 C3 1.379(3) . ?
C4 C7 1.381(3) 3_666 ?
C13 C12 1.507(3) . ?
C1 C9 1.492(2) . ?
C9 C10 1.518(2) . ?
C7 C4 1.381(3) 3_666 ?
C11 C12 1.517(2) . ?
C11 C10 1.523(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 N4 O5 122.34(19) . . ?
O6 N4 O4 118.99(18) . . ?
O5 N4 O4 118.66(17) . . ?
N1 Cu1 O1 91.80(5) . 3_666 ?
N1 Cu1 O1 168.18(6) . . ?
O1 Cu1 O1 80.00(5) 3_666 . ?
N1 Cu1 O2 80.77(5) . . ?
O1 Cu1 O2 165.43(6) 3_666 . ?
O1 Cu1 O2 105.25(5) . . ?
N1 Cu1 O4 99.92(6) . . ?
O1 Cu1 O4 109.46(6) 3_666 . ?
O1 Cu1 O4 90.89(6) . . ?
O2 Cu1 O4 84.29(7) . . ?
N1 Cu1 Cu1 131.54(4) . 3_666 ?
O1 Cu1 Cu1 40.29(3) 3_666 3_666 ?
O1 Cu1 Cu1 39.71(3) . 3_666 ?
O2 Cu1 Cu1 143.19(4) . 3_666 ?
O4 Cu1 Cu1 103.08(5) . 3_666 ?
C1 O2 Cu1 112.24(11) . . ?
C2 O1 Cu1 127.46(10) . 3_666 ?
C2 O1 Cu1 132.54(10) . . ?
Cu1 O1 Cu1 100.00(5) 3_666 . ?
C8 N1 N2 119.43(14) . . ?
C8 N1 Cu1 128.99(12) . . ?
N2 N1 Cu1 111.57(10) . . ?
N4 O4 Cu1 120.74(11) . . ?
C6 C5 C2 119.09(16) . 3_666 ?
C6 C5 C8 116.12(16) . . ?
C2 C5 C8 124.78(15) 3_666 . ?
C1 N2 N1 114.91(13) . . ?
N1 C8 C5 123.70(15) . . ?
C7 C6 C5 121.80(17) . . ?
O1 C2 C3 119.55(15) . . ?
O1 C2 C5 122.56(14) . 3_666 ?
C3 C2 C5 117.89(15) . 3_666 ?
C3 C4 C7 121.23(18) . 3_666 ?
O3 C13 C12 110.30(15) . . ?
C4 C3 C2 121.32(17) . . ?
O2 C1 N2 119.99(15) . . ?
O2 C1 C9 122.68(16) . . ?
N2 C1 C9 117.34(15) . . ?
C1 C9 C10 113.74(15) . . ?
C6 C7 C4 118.64(17) . 3_666 ?
C12 C11 C10 112.73(15) . . ?
C9 C10 C11 110.94(15) . . ?
C13 C12 C11 113.62(16) . . ?

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
O3 H3 O4 0.82 1.92 2.732(2) 173.8 2_746
N2 H2 O3 0.86 1.90 2.7416(19) 167.7 2_746
C3 H3A O2 0.93 2.18 3.027(2) 151.0 .

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NiHl@solv
_database_code_depnum_ccdc_archive 'CCDC 1858832'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2018-07-27 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H30 N4 Ni O9'
_chemical_formula_weight         673.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   22.063(9)
_cell_length_b                   5.803(2)
_cell_length_c                   24.656(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.727(7)
_cell_angle_gamma                90
_cell_volume                     3039(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2115
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      20.67

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.701
_shelx_estimated_absorpt_T_min   0.752
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART1000 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13416
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.716
_diffrn_reflns_theta_max         28.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3701
_reflns_number_gt                1845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1058P)²+8.5273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3701
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.2291
_refine_ls_wR_factor_gt          0.1721
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O20 O 0.1194(2) 0.8919(13) 0.12206(19) 0.111(2) Uani 1 1 d . . . . .
Ni1 Ni 0.2500 0.7500 0.5000 0.0411(3) Uani 1 2 d S . P . .
N2 N 0.2966(2) 0.4837(8) 0.4911(2) 0.0580(12) Uani 1 1 d . . . . .
O10 O 0.21431(19) 0.7153(7) 0.42375(17) 0.0639(11) Uani 1 1 d . . . . .
C3 C 0.1972(3) 0.2346(11) 0.2621(2) 0.0608(14) Uani 1 1 d . . . . .
H3 H 0.2063 0.0944 0.2477 0.073 Uiso 1 1 calc R U . . .
C2 C 0.2204(3) 0.2833(10) 0.3191(2) 0.0583(14) Uani 1 1 d . . . . .
H2 H 0.2446 0.1725 0.3425 0.070 Uiso 1 1 calc R U . . .
C1 C 0.2092(3) 0.4876(10) 0.3420(2) 0.0549(14) Uani 1 1 d . . . . .
C7 C 0.2368(3) 0.5396(9) 0.4053(3) 0.0556(14) Uani 1 1 d . . . . .
C6 C 0.1723(4) 0.6440(12) 0.3071(3) 0.0776(19) Uani 1 1 d . . . . .
H6 H 0.1631 0.7826 0.3221 0.093 Uiso 1 1 calc R U . . .
C4 C 0.1611(3) 0.3940(13) 0.2275(2) 0.0679(17) Uani 1 1 d . . . . .
C5 C 0.1478(4) 0.6035(12) 0.2497(3) 0.084(2) Uani 1 1 d . . . . .
H5 H 0.1231 0.7138 0.2265 0.101 Uiso 1 1 calc R U . . .
N1 N 0.28147(18) 0.4078(7) 0.43485(16) 0.0418(9) Uani 1 1 d . . . . .
O12 O 0.50341(19) -0.3536(7) 0.54369(18) 0.0727(12) Uani 1 1 d . . . . .
H12 H 0.4867 -0.4628 0.5242 0.109 Uiso 0.5 1 calc R U P . .
C11 C 0.4612(3) -0.1764(9) 0.5377(2) 0.0522(13) Uani 1 1 d . . . . .
C10 C 0.4131(2) -0.1517(9) 0.4881(2) 0.0515(13) Uani 1 1 d . . . . .
H10 H 0.4093 -0.2559 0.4587 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3770(3) 0.1860(9) 0.5270(3) 0.0572(15) Uani 1 1 d . . . . .
C9 C 0.3712(2) 0.0277(9) 0.4829(2) 0.0548(14) Uani 1 1 d . . . . .
H9 H 0.3389 0.0443 0.4499 0.066 Uiso 1 1 calc R U . . .
O11 O 0.1382(3) 0.3593(11) 0.17026(19) 0.1075(18) Uani 1 1 d . . . . .
H11 H 0.1410 0.2224 0.1631 0.161 Uiso 1 1 calc R U . . .
C14 C 0.3370(3) 0.3881(11) 0.5293(2) 0.0613(15) Uani 1 1 d . . . . .
H14 H 0.3430 0.4533 0.5649 0.074 Uiso 1 1 calc R U . . .
C12 C 0.4673(3) -0.0244(12) 0.5813(3) 0.0781(19) Uani 1 1 d . . . . .
H12A H 0.5000 -0.0411 0.6141 0.094 Uiso 1 1 calc R U . . .
C13 C 0.4249(3) 0.1528(13) 0.5764(3) 0.0760(19) Uani 1 1 d . . . . .
H13 H 0.4283 0.2526 0.6066 0.091 Uiso 1 1 calc R U . . .
C21 C 0.4882(10) 0.724(3) 0.2203(4) 0.221(9) Uani 1 1 d . . . . .
H21A H 0.4454 0.7823 0.2092 0.266 Uiso 1 1 calc R U . . .
H21B H 0.5141 0.8212 0.2036 0.266 Uiso 1 1 calc R U . . .
O1 O 0.5000 0.373(4) 0.2500 0.345(18) Uani 1 2 d S T P . .
C20 C 0.4899(13) 0.513(3) 0.2040(8) 0.297(15) Uani 1 1 d . . . . .
H20A H 0.5234 0.4932 0.1858 0.356 Uiso 1 1 calc R U . . .
H20B H 0.4503 0.4729 0.1771 0.356 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O10 1.842(4) 7_566 ?
Ni1 O10 1.842(4) . ?
Ni1 N2 1.901(5) . ?
Ni1 N2 1.901(5) 7_566 ?
N2 C14 1.238(7) . ?
N2 N1 1.407(6) . ?
O10 C7 1.272(6) . ?
C3 C4 1.361(8) . ?
C3 C2 1.387(7) . ?
C2 C1 1.366(8) . ?
C1 C6 1.359(9) . ?
C1 C7 1.541(8) . ?
C7 N1 1.303(6) . ?
C6 C5 1.393(9) . ?
C4 O11 1.378(7) . ?
C4 C5 1.396(10) . ?
O12 C11 1.368(6) . ?
C11 C12 1.369(8) . ?
C11 C10 1.392(7) . ?
C10 C9 1.374(7) . ?
C8 C13 1.394(8) . ?
C8 C9 1.403(8) . ?
C8 C14 1.478(8) . ?
C12 C13 1.373(9) . ?
C21 C20 1.296(18) . ?
C21 C21 1.41(2) 2_655 ?
O1 C20 1.363(18) . ?
O1 C20 1.363(18) 2_655 ?

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
O10 Ni1 O10 180.0 7_566 . ?
O10 Ni1 N2 96.39(19) 7_566 . ?
O10 Ni1 N2 83.61(19) . . ?
O10 Ni1 N2 83.61(19) 7_566 7_566 ?
O10 Ni1 N2 96.39(19) . 7_566 ?
N2 Ni1 N2 180.00(16) . 7_566 ?
C14 N2 N1 122.6(5) . . ?
C14 N2 Ni1 125.2(5) . . ?
N1 N2 Ni1 112.1(3) . . ?
C7 O10 Ni1 110.7(4) . . ?
C4 C3 C2 119.3(6) . . ?
C1 C2 C3 122.6(6) . . ?
C6 C1 C2 117.5(6) . . ?
C6 C1 C7 120.9(5) . . ?
C2 C1 C7 121.5(5) . . ?
O10 C7 N1 125.4(5) . . ?
O10 C7 C1 115.7(5) . . ?
N1 C7 C1 118.9(5) . . ?
C1 C6 C5 122.1(6) . . ?
C3 C4 O11 122.2(6) . . ?
C3 C4 C5 119.7(6) . . ?
O11 C4 C5 118.1(6) . . ?
C6 C5 C4 118.8(6) . . ?
C7 N1 N2 108.0(4) . . ?
O12 C11 C12 118.7(5) . . ?
O12 C11 C10 120.5(5) . . ?
C12 C11 C10 120.9(5) . . ?
C9 C10 C11 119.6(5) . . ?
C13 C8 C9 118.4(5) . . ?
C13 C8 C14 113.3(6) . . ?
C9 C8 C14 128.3(6) . . ?
C10 C9 C8 120.4(5) . . ?
N2 C14 C8 129.8(6) . . ?
C11 C12 C13 119.6(6) . . ?
C12 C13 C8 121.2(6) . . ?
C20 C21 C21 106.7(11) . 2_655 ?
C20 O1 C20 107(2) . 2_655 ?
C21 C20 O1 108.6(19) . . ?

_refine_diff_density_max         0.949
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.092

_shelxl_version_number           2013-4


# start Validation Reply Form
_vrf_PLAT230_NiHl@solv           
;
PROBLEM: Hirshfeld Test Diff for   N1       --N2        .        8.0 s.u.  
RESPONSE: The nature of the ligand has been established by other spectroscopic
techniques such as NMR, IR and elemental analysis. The disorder imposed by the
solvent (THF) in the crystals is likely affecting to the other parts of the model.
;
_vrf_PLAT306_NiHl@solv           
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O20 Check 
RESPONSE: The presence of water in the net has been also established by other 
spectroscopic techniques such as NMR, IR and elemental analysis.
;
_vrf_PLAT360_NiHl@solv           
;
PROBLEM: Short  C(sp3)-C(sp3) Bond  C20      - C21      .       1.29 Ang.  
RESPONSE: The THF molecule is present in the crystal but with rather 
high values of the anisotropic factors. This suggests that the solvent 
molecule is disordered and, consequently, the interatomic distances are 
not significant.
;
# end Validation Reply Form 
