# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1570203'
_audit_update_record             
;
2018-05-04 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-05-01
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H40 B2 F8 N12 O6 Zn'
_chemical_formula_sum            'C24 H40 B2 F8 N12 O6 Zn'
_chemical_formula_weight         831.67
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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                   14.0391(17)
_cell_length_b                   16.899(2)
_cell_length_c                   8.8800(14)
_cell_angle_alpha                90
_cell_angle_beta                 109.629(5)
_cell_angle_gamma                90
_cell_volume                     1984.3(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.985
_cell_measurement_theta_min      2.410
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.854
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.8314
_exptl_absorpt_correction_T_min  0.8125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            29736
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.985
_diffrn_reflns_theta_max         24.985
_diffrn_reflns_theta_min         2.410
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1473
_reflns_number_total             1814
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1814
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+3.6174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 B2-F3 \\sim B2-F4 \\sim B2-F5 \\sim B2-F6
 with sigma of 0.02
 F3-F4 \\sim F4-F5 \\sim F5-F6 \\sim F6-F3 \\sim F4-F6 \\sim F3-F5
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
B2 \\sim F3 \\sim F4 \\sim F5 \\sim F6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(B2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 B2, F3, F4, F5, F6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Others
 Fixed Sof: B2(0.5) F3(0.5) F4(0.5) F5(0.5) F6(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.000000 0.000000 -0.500000 0.0358(3) Uani 1 4 d S T P . .
O1 O -0.36765(19) -0.20283(17) -0.6839(3) 0.0552(7) Uani 1 1 d . . . . .
O2 O -0.500000 -0.1666(2) -0.500000 0.0553(10) Uani 1 2 d S T P . .
N1 N -0.0835(2) -0.09034(16) -0.6518(3) 0.0382(7) Uani 1 1 d . . . . .
N2 N -0.1559(3) -0.16910(19) -0.8616(4) 0.0579(10) Uani 1 1 d . . . . .
N3 N -0.1733(2) -0.19648(16) -0.7299(3) 0.0361(7) Uani 1 1 d . . . . .
C1 C -0.1298(3) -0.1496(2) -0.6085(4) 0.0416(9) Uani 1 1 d . . . . .
H1 H -0.131324 -0.157082 -0.505574 0.050 Uiso 1 1 calc R . . . .
C2 C -0.1012(3) -0.1060(2) -0.8088(4) 0.0528(11) Uani 1 1 d . . . . .
H2 H -0.076537 -0.074439 -0.873262 0.063 Uiso 1 1 calc R . . . .
C3 C -0.2343(3) -0.2675(2) -0.7387(4) 0.0458(10) Uani 1 1 d . . . . .
H3A H -0.216904 -0.290980 -0.633222 0.055 Uiso 1 1 calc R . . . .
H3B H -0.219259 -0.305783 -0.808914 0.055 Uiso 1 1 calc R . . . .
C4 C -0.3447(3) -0.2488(3) -0.7998(5) 0.0549(11) Uani 1 1 d . . . . .
H4A H -0.361481 -0.219662 -0.899486 0.066 Uiso 1 1 calc R . . . .
H4B H -0.383903 -0.297292 -0.819467 0.066 Uiso 1 1 calc R . . . .
C5 C -0.4650(3) -0.1693(3) -0.7446(5) 0.0638(12) Uani 1 1 d . . . . .
H5A H -0.515309 -0.210998 -0.776837 0.077 Uiso 1 1 calc R . . . .
H5B H -0.470367 -0.137405 -0.837949 0.077 Uiso 1 1 calc R . . . .
C6 C -0.4841(4) -0.1193(3) -0.6204(6) 0.0660(12) Uani 1 1 d . . . . .
H6A H -0.426728 -0.084688 -0.573186 0.079 Uiso 1 1 calc R . . . .
H6B H -0.543195 -0.086534 -0.669289 0.079 Uiso 1 1 calc R . . . .
B2 B 0.1681(5) -0.0008(10) -0.7187(8) 0.0503(18) Uani 0.5 1 d D U . A -1
F3 F 0.1948(12) -0.0746(7) -0.716(2) 0.186(6) Uani 0.5 1 d D U . A -1
F4 F 0.1131(9) 0.0222(8) -0.8653(8) 0.185(7) Uani 0.5 1 d D U . A -1
F5 F 0.1071(4) 0.009(2) -0.6319(6) 0.101(4) Uani 0.5 1 d D U . A -1
F6 F 0.2438(9) 0.0468(9) -0.665(3) 0.233(9) Uani 0.5 1 d D U . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.112(3) . ?
Zn1 N1 2.112(3) 6 ?
Zn1 N1 2.112(3) 5_554 ?
Zn1 N1 2.112(3) 2_554 ?
Zn1 F5 2.200(5) . ?
O1 C4 1.410(4) . ?
O1 C5 1.409(5) . ?
O2 C6 1.412(5) 2_454 ?
O2 C6 1.412(5) . ?
N1 C1 1.319(4) . ?
N1 C2 1.357(4) . ?
N2 N3 1.353(4) . ?
N2 C2 1.306(5) . ?
N3 C1 1.312(4) . ?
N3 C3 1.461(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.494(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.484(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
B2 F3 1.301(12) . ?
B2 F4 1.329(10) . ?
B2 F5 1.340(8) . ?
B2 F6 1.289(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 Zn1 N1 180.0 . 5_554 ?
N1 Zn1 N1 180.0 6 2_554 ?
N1 Zn1 N1 87.44(15) . 2_554 ?
N1 Zn1 N1 92.56(15) . 6 ?
N1 Zn1 N1 87.44(15) 5_554 6 ?
N1 Zn1 N1 92.56(15) 5_554 2_554 ?
N1 Zn1 F5 87.7(7) 5_554 . ?
N1 Zn1 F5 93.2(6) 2_554 . ?
N1 Zn1 F5 86.8(6) 6 . ?
N1 Zn1 F5 92.3(7) . . ?
C5 O1 C4 111.8(3) . . ?
C6 O2 C6 111.0(5) . 2_454 ?
C1 N1 Zn1 125.7(2) . . ?
C1 N1 C2 102.4(3) . . ?
C2 N1 Zn1 131.8(2) . . ?
C2 N2 N3 103.0(3) . . ?
N2 N3 C3 120.5(3) . . ?
C1 N3 N2 109.5(3) . . ?
C1 N3 C3 130.0(3) . . ?
N1 C1 H1 124.5 . . ?
N3 C1 N1 110.9(3) . . ?
N3 C1 H1 124.5 . . ?
N1 C2 H2 122.9 . . ?
N2 C2 N1 114.2(3) . . ?
N2 C2 H2 122.9 . . ?
N3 C3 H3A 109.4 . . ?
N3 C3 H3B 109.4 . . ?
N3 C3 C4 111.3(3) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
O1 C4 C3 108.3(3) . . ?
O1 C4 H4A 110.0 . . ?
O1 C4 H4B 110.0 . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
O1 C5 H5A 109.7 . . ?
O1 C5 H5B 109.7 . . ?
O1 C5 C6 109.8(3) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
O2 C6 C5 110.8(4) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
F3 B2 F4 111.5(12) . . ?
F3 B2 F5 109.8(16) . . ?
F4 B2 F5 104.7(8) . . ?
F6 B2 F3 113.3(11) . . ?
F6 B2 F4 108.3(13) . . ?
F6 B2 F5 108.7(14) . . ?
B2 F5 Zn1 169(2) . . ?

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
Zn1 N1 C1 N3 -178.7(2) . . . . ?
Zn1 N1 C2 N2 178.8(3) . . . . ?
O1 C5 C6 O2 -72.9(4) . . . . ?
N2 N3 C1 N1 0.5(4) . . . . ?
N2 N3 C3 C4 -82.5(4) . . . . ?
N3 N2 C2 N1 -0.9(5) . . . . ?
N3 C3 C4 O1 -67.9(4) . . . . ?
C1 N1 C2 N2 1.2(5) . . . . ?
C1 N3 C3 C4 96.2(4) . . . . ?
C2 N1 C1 N3 -1.0(4) . . . . ?
C2 N2 N3 C1 0.3(4) . . . . ?
C2 N2 N3 C3 179.2(3) . . . . ?
C3 N3 C1 N1 -178.3(3) . . . . ?
C4 O1 C5 C6 -178.0(4) . . . . ?
C5 O1 C4 C3 168.0(3) . . . . ?
C6 O2 C6 C5 178.6(4) 2_454 . . . ?
F3 B2 F5 Zn1 -25(4) . . . . ?
F4 B2 F5 Zn1 94(4) . . . . ?
F6 B2 F5 Zn1 -150(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1570228'
_audit_update_record             
;
2018-02-18 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H40 Cu N14 O12'
_chemical_formula_weight         780.24

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'
Cu Cu 0.3201 1.2651 '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'

_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                   13.9407(14)
_cell_length_b                   16.0084(15)
_cell_length_c                   8.8745(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.972(4)
_cell_angle_gamma                90
_cell_volume                     1849.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1710
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             814
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.665
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8215
_exptl_absorpt_correction_T_max  0.9156
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   sadabs
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26770
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1702
_reflns_number_gt                1378
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'MERCURY 3.1'
_computing_publication_material  'ORTEP 3v.2'
_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)+(0.1309P)²+9.1358P] 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         1702
_refine_ls_number_parameters     123
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.2405
_refine_ls_wR_factor_gt          0.2202
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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
Cu1 Cu -1.000000 0.000000 -0.500000 0.0361(5) Uani 1 4 d S T P . .
O1 O -0.3708(3) -0.2064(3) -0.6822(5) 0.0620(13) Uani 1 1 d . . . . .
O2 O -0.500000 -0.1667(4) -0.500000 0.0675(18) Uani 1 2 d S T P . .
O4 O -0.7495(10) 0.000000 -0.732(3) 0.128(4) Uiso 0.6 2 d DS . P A 1
O5 O -0.9028(14) 0.000000 -0.8640(16) 0.128(4) Uiso 0.6 2 d DS . P A 1
O6 O -0.8681(17) 0.000000 -0.615(2) 0.128(4) Uiso 0.6 2 d DS . P A 1
O4A O -0.7596(17) 0.0333(16) -0.623(3) 0.097(6) Uiso 0.2 1 d D . P A 2
O5A O -0.9009(18) 0.0307(16) -0.677(3) 0.097(6) Uiso 0.2 1 d D . P A 2
O6A O -0.814(3) -0.0445(13) -0.823(3) 0.097(6) Uiso 0.2 1 d D . P A 2
N1 N -0.1603(5) -0.1708(4) -0.8588(6) 0.0676(17) Uani 1 1 d . . . . .
N2 N -0.0833(3) -0.0900(3) -0.6469(5) 0.0366(10) Uani 1 1 d . . . . .
N3 N -0.1764(4) -0.2007(3) -0.7285(5) 0.0418(11) Uani 1 1 d . . . . .
N7 N -0.8363(7) 0.000000 -0.7264(10) 0.061(2) Uani 1 2 d DS T P . .
C1 C -0.1039(6) -0.1049(4) -0.8045(7) 0.0620(18) Uani 1 1 d . . . . .
H1A H -0.080045 -0.071114 -0.868866 0.074 Uiso 1 1 calc R U . . .
C2 C -0.1296(4) -0.1525(3) -0.6044(6) 0.0411(13) Uani 1 1 d . . . . .
H2A H -0.129181 -0.161226 -0.500533 0.049 Uiso 1 1 calc R U . . .
C3 C -0.2387(5) -0.2754(4) -0.7382(7) 0.0503(15) Uani 1 1 d . . . . .
H3A H -0.220115 -0.300241 -0.631867 0.060 Uiso 1 1 calc R U . . .
H3B H -0.224604 -0.315919 -0.808863 0.060 Uiso 1 1 calc R U . . .
C4 C -0.3498(5) -0.2549(5) -0.8005(7) 0.0625(18) Uani 1 1 d . . . . .
H4A H -0.367413 -0.223812 -0.900523 0.075 Uiso 1 1 calc R U . . .
H4B H -0.390160 -0.305857 -0.821510 0.075 Uiso 1 1 calc R U . . .
C5 C -0.4659(6) -0.1658(6) -0.7439(10) 0.077(2) Uani 1 1 d . . . . .
H5A H -0.520400 -0.206872 -0.782302 0.093 Uiso 1 1 calc R U . . .
H5B H -0.468081 -0.130897 -0.834471 0.093 Uiso 1 1 calc R U . . .
C6 C -0.4820(7) -0.1146(5) -0.6201(11) 0.084(2) Uani 1 1 d . . . . .
H6A H -0.421992 -0.079935 -0.569140 0.101 Uiso 1 1 calc R U . . .
H6B H -0.540516 -0.078167 -0.668798 0.101 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
Cu1 N2 2.010(4) 5_454 ?
Cu1 N2 2.010(4) 1_455 ?
Cu1 N2 2.010(4) 6_455 ?
Cu1 N2 2.010(4) 2_454 ?
Cu1 O6 2.402(14) 5_354 ?
Cu1 O6 2.402(14) . ?
O1 C5 1.400(9) . ?
O1 C4 1.419(8) . ?
O2 C6 1.444(9) . ?
O2 C6 1.444(9) 2_454 ?
O4 N7 1.228(8) . ?
O5 N7 1.241(8) . ?
O6 N7 1.220(8) . ?
O4A O4A 1.07(5) 6 ?
O4A N7 1.250(9) . ?
O4A O6A 1.67(3) 6 ?
O4A O5A 1.85(3) . ?
O5A O5A 0.98(5) 6 ?
O5A N7 1.236(9) . ?
O6A N7 1.235(9) . ?
O6A O6A 1.43(4) 6 ?
N1 C1 1.300(8) . ?
N1 N3 1.344(7) . ?
N2 C2 1.317(7) . ?
N2 C1 1.344(7) . ?
N3 C2 1.312(7) . ?
N3 C3 1.461(7) . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C4 1.483(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.451(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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
N2 Cu1 N2 180.00(17) 5_454 1_455 ?
N2 Cu1 N2 88.4(2) 5_454 6_455 ?
N2 Cu1 N2 91.6(2) 1_455 6_455 ?
N2 Cu1 N2 91.6(2) 5_454 2_454 ?
N2 Cu1 N2 88.4(2) 1_455 2_454 ?
N2 Cu1 N2 180.0(2) 6_455 2_454 ?
N2 Cu1 O6 94.4(4) 5_454 5_354 ?
N2 Cu1 O6 85.6(4) 1_455 5_354 ?
N2 Cu1 O6 85.6(4) 6_455 5_354 ?
N2 Cu1 O6 94.4(4) 2_454 5_354 ?
N2 Cu1 O6 85.6(4) 5_454 . ?
N2 Cu1 O6 94.4(4) 1_455 . ?
N2 Cu1 O6 94.4(4) 6_455 . ?
N2 Cu1 O6 85.6(4) 2_454 . ?
O6 Cu1 O6 180.0 5_354 . ?
C5 O1 C4 112.5(5) . . ?
C6 O2 C6 109.5(8) . 2_454 ?
N7 O6 Cu1 154.2(16) . . ?
O4A O4A N7 64.8(13) 6 . ?
N7 O4A O6A 47.5(10) . 6 ?
O4A O4A O5A 88.7(12) 6 . ?
N7 O4A O5A 41.5(11) . . ?
O6A O4A O5A 72.0(15) 6 . ?
O5A O5A N7 66.6(13) 6 . ?
O5A O5A O4A 91.3(12) 6 . ?
N7 O5A O4A 42.1(11) . . ?
N7 O6A O6A 54.7(12) . 6 ?
N7 O6A O4A 48.2(11) . 6 ?
C1 N1 N3 103.7(5) . . ?
C2 N2 C1 102.7(4) . . ?
C2 N2 Cu1 125.9(3) . 1_655 ?
C1 N2 Cu1 131.3(4) . 1_655 ?
C2 N3 N1 109.0(5) . . ?
C2 N3 C3 129.6(5) . . ?
N1 N3 C3 121.4(4) . . ?
O6 N7 O4 133.0(17) . . ?
O6 N7 O5A 35.9(13) . 6 ?
O4 N7 O5A 150.2(16) . 6 ?
O6 N7 O6A 144.6(12) . 6 ?
O4 N7 O6A 58.5(15) . 6 ?
O5A N7 O6A 150(2) . . ?
O5A N7 O6A 114(2) 6 . ?
O6A N7 O6A 71(2) 6 . ?
O6 N7 O5 116.0(16) . . ?
O4 N7 O5 111.1(16) . . ?
O5A N7 O4A 96(2) . . ?
O5A N7 O4A 116.7(19) 6 . ?
O6A N7 O4A 84(2) 6 . ?
O6A N7 O4A 113(2) . . ?
O6 N7 O4A 82.6(18) . 6 ?
O4 N7 O4A 55.5(15) . 6 ?
O5 N7 O4A 149.5(15) . 6 ?
N1 C1 N2 113.9(5) . . ?
N1 C1 H1A 123.1 . . ?
N2 C1 H1A 123.1 . . ?
N3 C2 N2 110.7(5) . . ?
N3 C2 H2A 124.6 . . ?
N2 C2 H2A 124.6 . . ?
N3 C3 C4 111.1(5) . . ?
N3 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N3 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 C3 108.1(5) . . ?
O1 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
O1 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
O1 C5 C6 110.3(6) . . ?
O1 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
O1 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
O2 C6 C5 110.4(7) . . ?
O2 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
O2 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?

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
O4A O4A O5A O5A 0.002(1) 6 . . 6 ?
N7 O4A O5A O5A 51.9(11) . . . 6 ?
O6A O4A O5A O5A 96.9(9) 6 . . 6 ?
O4A O4A O5A N7 -51.9(11) 6 . . . ?
O6A O4A O5A N7 45.1(16) 6 . . . ?
C1 N1 N3 C2 -0.2(8) . . . . ?
C1 N1 N3 C3 179.2(6) . . . . ?
Cu1 O6 N7 O4 180.000(8) . . . . ?
Cu1 O6 N7 O5 0.000(5) . . . . ?
O4A O5A N7 O5A 121.0(14) . . . 6 ?
O5A O5A N7 O6A 152.3(18) 6 . . 6 ?
O4A O5A N7 O6A -87(2) . . . 6 ?
O5A O5A N7 O6A 59.2(15) 6 . . . ?
O4A O5A N7 O6A -179.8(6) . . . . ?
O5A O5A N7 O4A -121.0(14) 6 . . . ?
O5A O5A N7 O4A -72.4(18) 6 . . 6 ?
O4A O5A N7 O4A 49(3) . . . 6 ?
O6A O6A N7 O5A 105.2(18) 6 . . . ?
O4A O6A N7 O5A -138(2) 6 . . . ?
O6A O6A N7 O5A 149(2) 6 . . 6 ?
O4A O6A N7 O5A -94(2) 6 . . 6 ?
O4A O6A N7 O6A 117.0(17) 6 . . 6 ?
O6A O6A N7 O4A -74.6(17) 6 . . . ?
O4A O6A N7 O4A 42(2) 6 . . . ?
O6A O6A N7 O4A -117.0(17) 6 . . 6 ?
O4A O4A N7 O5A 119.6(13) 6 . . . ?
O6A O4A N7 O5A -114(2) 6 . . . ?
O4A O4A N7 O5A 75.3(19) 6 . . 6 ?
O6A O4A N7 O5A -158(2) 6 . . 6 ?
O5A O4A N7 O5A -44(3) . . . 6 ?
O4A O4A N7 O6A -126.5(14) 6 . . 6 ?
O5A O4A N7 O6A 114(2) . . . 6 ?
O4A O4A N7 O6A -60.5(13) 6 . . . ?
O6A O4A N7 O6A 66(2) 6 . . . ?
O5A O4A N7 O6A 179.9(3) . . . . ?
O6A O4A N7 O4A 126.5(14) 6 . . 6 ?
O5A O4A N7 O4A -119.6(13) . . . 6 ?
N3 N1 C1 N2 -0.5(9) . . . . ?
C2 N2 C1 N1 1.0(8) . . . . ?
Cu1 N2 C1 N1 179.0(5) 1_655 . . . ?
N1 N3 C2 N2 0.8(7) . . . . ?
C3 N3 C2 N2 -178.5(5) . . . . ?
C1 N2 C2 N3 -1.1(7) . . . . ?
Cu1 N2 C2 N3 -179.2(3) 1_655 . . . ?
C2 N3 C3 C4 97.4(7) . . . . ?
N1 N3 C3 C4 -81.8(7) . . . . ?
C5 O1 C4 C3 164.4(6) . . . . ?
N3 C3 C4 O1 -68.3(7) . . . . ?
C4 O1 C5 C6 -177.9(6) . . . . ?
C6 O2 C6 C5 -178.7(9) 2_454 . . . ?
O1 C5 C6 O2 -71.0(8) . . . . ?

_refine_diff_density_max         1.190
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.113

