# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1575107'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_shelx               
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: The molecule is achiral. There is only one oxygen atom and there  are no other atoms with considerable anomalous dispersion effect.
;
# Added during the CSD deposition process: Monday 18 September 2017 01:31 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        7-(piperidin-1-ylmethyl)quinolin-8-ol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N2 O'
_chemical_formula_sum            'C15 H18 N2 O'
_chemical_formula_weight         242.31

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.9362(7)
_cell_length_b                   11.4735(10)
_cell_length_c                   12.7458(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1306.82(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24530
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.40

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       RX
_diffrn_measurement_device       RAXIS-RAPID
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           40.0000
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       dtprofit.ref
_diffrn_measurement_details      
;
 scan:  N=1,PHI=0.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                  
 scan:  N=2,PHI=180.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                
 scan:  N=3,PHI=0.0,CHI=0.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                   
 scan:  N=4,PHI=90.0,CHI=0.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                  
 Orientation Matrix:
    UB11 -0.0633 UB12 -0.0285 UB13 -0.0594
    UB21  0.0213 UB22  0.0734 UB23 -0.0396
    UB31  0.0898 UB32 -0.0375 UB33 -0.0325
    Matrix type: 'd*Trek'
;
_diffrn_reflns_number            41004
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.197
_diffrn_reflns_theta_max         27.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2956
_reflns_number_gt                2309
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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.
The molecule is achiral. There is only one oxygen atom and there 
are no other atoms with considerable anomalous dispersion effect.
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'Sir2014 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2006)'
_computing_publication_material  'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_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)+(0.0895P)²+0.0073P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 775 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2956
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1402
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
O1 O 0.8570(2) 0.81438(17) 0.32001(14) 0.0633(5) Uani 1 1 d . . . . .
C7 C 0.7215(3) 0.7990(2) 0.48149(18) 0.0561(6) Uani 1 1 d . . . . .
N10 N 0.6900(2) 0.62856(18) 0.36243(17) 0.0599(6) Uani 1 1 d . . . . .
N1 N 0.9062(3) 1.0459(2) 0.35370(17) 0.0652(6) Uani 1 1 d . . . . .
C8A C 0.8222(2) 0.9858(2) 0.42484(18) 0.0530(6) Uani 1 1 d . . . . .
C8 C 0.7989(3) 0.8638(2) 0.40897(17) 0.0528(6) Uani 1 1 d . . . . .
C4A C 0.7583(3) 1.0393(2) 0.51473(19) 0.0585(6) Uani 1 1 d . . . . .
C6 C 0.6585(3) 0.8549(3) 0.56959(19) 0.0658(7) Uani 1 1 d . . . . .
H6 H 0.6043 0.8106 0.6175 0.079 Uiso 1 1 calc R U . . .
C9 C 0.7147(3) 0.6671(2) 0.4713(2) 0.0697(8) Uani 1 1 d . . . . .
H9A H 0.8078 0.6340 0.4968 0.084 Uiso 1 1 calc R U . . .
H9B H 0.6344 0.6377 0.5151 0.092(10) Uiso 1 1 calc R . . . .
C5 C 0.6741(3) 0.9720(3) 0.5870(2) 0.0670(7) Uani 1 1 d . . . . .
H5 H 0.6303 1.0068 0.6453 0.080 Uiso 1 1 calc R U . . .
C2 C 0.9277(4) 1.1583(3) 0.3726(2) 0.0775(8) Uani 1 1 d . . . . .
H2 H 0.9838 1.2004 0.3243 0.093 Uiso 1 1 calc R U . . .
C11 C 0.5366(3) 0.6540(2) 0.3300(2) 0.0601(6) Uani 1 1 d . . . . .
H11A H 0.5179 0.7369 0.3373 0.072 Uiso 1 1 calc R U . . .
H11B H 0.4675 0.6131 0.3758 0.072 Uiso 1 1 calc R U . . .
C13 C 0.5403(4) 0.4890(3) 0.2030(3) 0.0837(9) Uani 1 1 d . . . . .
H13B H 0.4684 0.4433 0.2424 0.100 Uiso 1 1 calc R U . . .
H13A H 0.5309 0.4688 0.1295 0.100 Uiso 1 1 calc R U . . .
C4 C 0.7866(3) 1.1591(2) 0.5301(2) 0.0728(8) Uani 1 1 d . . . . .
H4 H 0.7468 1.1975 0.5880 0.087 Uiso 1 1 calc R U . . .
C15 C 0.7200(4) 0.5026(3) 0.3515(3) 0.0877(10) Uani 1 1 d . . . . .
H15A H 0.6542 0.4595 0.3980 0.105 Uiso 1 1 calc R U . . .
H15B H 0.8224 0.4866 0.3722 0.105 Uiso 1 1 calc R U . . .
C12 C 0.5083(4) 0.6179(3) 0.2179(2) 0.0761(9) Uani 1 1 d . . . . .
H12B H 0.5718 0.6631 0.1714 0.091 Uiso 1 1 calc R U . . .
H12A H 0.4049 0.6339 0.1997 0.091 Uiso 1 1 calc R U . . .
C3 C 0.8722(4) 1.2181(3) 0.4599(3) 0.0807(9) Uani 1 1 d . . . . .
H3 H 0.8934 1.2967 0.4697 0.097 Uiso 1 1 calc R U . . .
C14 C 0.6960(4) 0.4619(3) 0.2404(4) 0.1014(12) Uani 1 1 d . . . . .
H14A H 0.7681 0.4997 0.1948 0.122 Uiso 1 1 calc R U . . .
H14B H 0.7128 0.3785 0.2366 0.122 Uiso 1 1 calc R U . . .
H1O H 0.804(6) 0.737(4) 0.326(4) 0.124(14) 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 1.370(3) . ?
O1 H1O 1.01(5) . ?
C7 C8 1.373(3) . ?
C7 C6 1.411(4) . ?
C7 C9 1.520(4) . ?
N10 C11 1.461(3) . ?
N10 C9 1.473(3) . ?
N10 C15 1.477(4) . ?
N1 C2 1.326(4) . ?
N1 C8A 1.364(3) . ?
C8A C4A 1.420(3) . ?
C8A C8 1.430(3) . ?
C4A C4 1.412(4) . ?
C4A C5 1.418(4) . ?
C6 C5 1.369(4) . ?
C6 H6 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C5 H5 0.9300 . ?
C2 C3 1.398(4) . ?
C2 H2 0.9300 . ?
C11 C12 1.510(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C14 1.503(5) . ?
C13 C12 1.518(5) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C4 C3 1.357(4) . ?
C4 H4 0.9300 . ?
C15 C14 1.506(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C3 H3 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 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
C8 O1 H1O 97(3) . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 C9 120.1(2) . . ?
C6 C7 C9 120.3(2) . . ?
C11 N10 C9 110.3(2) . . ?
C11 N10 C15 109.8(2) . . ?
C9 N10 C15 110.8(2) . . ?
C2 N1 C8A 116.8(2) . . ?
N1 C8A C4A 122.7(2) . . ?
N1 C8A C8 118.8(2) . . ?
C4A C8A C8 118.6(2) . . ?
O1 C8 C7 121.6(2) . . ?
O1 C8 C8A 117.8(2) . . ?
C7 C8 C8A 120.6(2) . . ?
C4 C4A C5 122.4(3) . . ?
C4 C4A C8A 117.4(2) . . ?
C5 C4A C8A 120.2(2) . . ?
C5 C6 C7 122.3(2) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
N10 C9 C7 112.7(2) . . ?
N10 C9 H9A 109.1 . . ?
C7 C9 H9A 109.1 . . ?
N10 C9 H9B 109.1 . . ?
C7 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C6 C5 C4A 118.9(2) . . ?
C6 C5 H5 120.6 . . ?
C4A C5 H5 120.6 . . ?
N1 C2 C3 124.8(3) . . ?
N1 C2 H2 117.6 . . ?
C3 C2 H2 117.6 . . ?
N10 C11 C12 111.7(2) . . ?
N10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C14 C13 C12 109.7(3) . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
H13B C13 H13A 108.2 . . ?
C3 C4 C4A 119.7(3) . . ?
C3 C4 H4 120.1 . . ?
C4A C4 H4 120.1 . . ?
N10 C15 C14 111.5(3) . . ?
N10 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
N10 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C11 C12 C13 110.7(3) . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
H12B C12 H12A 108.1 . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C13 C14 C15 111.4(3) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1575109'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'bis(7-(morpholin-4-ylmethyl)quinolin-8-ol)-bis-(μ-2-(7-(morpholin-4-ylmethyl)quinolin-8-ol)-di-copper(II) tetrachlorid dimethanol solvate dihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C56 H64 Cu2 N8 O8, 2(C H4 O), Cl4, 2(H2 O)
;
_chemical_formula_sum            'C58 H76 Cl4 Cu2 N8 O12'
_chemical_formula_weight         1346.14

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'
Cl Cl 0.1484 0.1585 '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                   25.0347(19)
_cell_length_b                   10.5428(7)
_cell_length_c                   23.7514(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.299(2)
_cell_angle_gamma                90
_cell_volume                     6258.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    28431
_cell_measurement_theta_min      3.115
_cell_measurement_theta_max      25.315

_exptl_crystal_description       Chip
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             2808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.916
_shelx_estimated_absorpt_T_min   0.803
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.780337
_exptl_absorpt_correction_T_max  0.881580
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           40.0000
_diffrn_radiation_detector       RX
_diffrn_measurement_device       RAXIS-RAPID

_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       dtprofit.ref
_diffrn_measurement_details      
;
 scan:  N=1,PHI=90.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                 
 scan:  N=2,PHI=270.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                
 scan:  N=3,PHI=0.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                  
 scan:  N=4,PHI=0.0,CHI=0.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                   
 Orientation Matrix:
    UB11 -0.0046 UB12  0.0450 UB13  0.0365
    UB21  0.0397 UB22  0.0079 UB23  0.0060
    UB31 -0.0013 UB32  0.0831 UB33 -0.0203
    Matrix type: 'd*Trek'
;
_diffrn_reflns_number            69245
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.1184
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.116
_diffrn_reflns_theta_max         25.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5720
_reflns_number_gt                4123
_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       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'Sir2014 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2006)'
_computing_publication_material  'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_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)+(0.0530P)²+14.9002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5720
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
Cu1 Cu 0.22486(2) 0.34279(5) 0.05050(2) 0.03968(17) Uani 1 1 d . . . . .
O11 O 0.23422(11) 0.1044(3) 0.01306(11) 0.0390(7) Uani 1 1 d . . . . .
O1 O 0.18472(11) 0.2891(3) 0.11334(11) 0.0396(7) Uani 1 1 d . . . . .
N1 N 0.15308(14) 0.3651(3) 0.01135(14) 0.0367(8) Uani 1 1 d . . . . .
N21 N 0.20534(14) 0.1515(3) -0.09290(14) 0.0388(8) Uani 1 1 d . . . . .
N30 N 0.18678(15) -0.1472(3) 0.10040(16) 0.0395(9) Uani 1 1 d . . . . .
C7 C 0.09478(17) 0.2433(4) 0.13694(17) 0.0383(10) Uani 1 1 d . . . . .
O13 O 0.14794(14) 0.3889(4) 0.34590(14) 0.0676(11) Uani 1 1 d . . . . .
N10 N 0.10602(16) 0.2756(4) 0.24277(15) 0.0401(9) Uani 1 1 d . . . . .
C28A C 0.16758(17) 0.0984(4) -0.06130(18) 0.0379(10) Uani 1 1 d . . . . .
C28 C 0.18511(17) 0.0717(4) -0.00391(18) 0.0371(10) Uani 1 1 d . . . . .
O33 O 0.21980(16) -0.3944(3) 0.06898(15) 0.0668(10) Uani 1 1 d . . . . .
C27 C 0.14844(18) 0.0139(4) 0.02984(18) 0.0402(10) Uani 1 1 d . . . . .
C8A C 0.11389(16) 0.3277(4) 0.04583(17) 0.0351(9) Uani 1 1 d . . . . .
C9 C 0.11181(19) 0.1875(4) 0.19333(17) 0.0417(11) Uani 1 1 d . . . . .
H9A H 0.1490 0.1618 0.1927 0.050 Uiso 1 1 calc R U . . .
H9B H 0.0908 0.1119 0.1991 0.050 Uiso 1 1 calc R U . . .
C24A C 0.11525(19) 0.0742(4) -0.0829(2) 0.0469(12) Uani 1 1 d . . . . .
C8 C 0.13293(17) 0.2862(4) 0.10085(16) 0.0344(10) Uani 1 1 d . . . . .
C4A C 0.05899(18) 0.3294(5) 0.02826(19) 0.0479(11) Uani 1 1 d . . . . .
C23 C 0.1408(2) 0.1626(6) -0.1703(2) 0.0623(14) Uani 1 1 d . . . . .
H23 H 0.1327 0.1854 -0.2076 0.075 Uiso 1 1 calc R U . . .
C3 C 0.0856(2) 0.4140(5) -0.0602(2) 0.0579(14) Uani 1 1 d . . . . .
H3 H 0.0770 0.4457 -0.0961 0.069 Uiso 1 1 calc R U . . .
C2 C 0.13911(19) 0.4067(4) -0.04001(18) 0.0457(11) Uani 1 1 d . . . . .
H2 H 0.1657 0.4318 -0.0634 0.055 Uiso 1 1 calc R U . . .
C6 C 0.04023(19) 0.2428(5) 0.1184(2) 0.0539(13) Uani 1 1 d . . . . .
H6 H 0.0154 0.2122 0.1428 0.065 Uiso 1 1 calc R U . . .
C26 C 0.09557(19) -0.0095(4) 0.0078(2) 0.0521(13) Uani 1 1 d . . . . .
H26 H 0.0713 -0.0457 0.0313 0.063 Uiso 1 1 calc R U . . .
C15 C 0.1455(2) 0.3820(5) 0.2432(2) 0.0501(12) Uani 1 1 d . . . . .
H15A H 0.1391 0.4337 0.2097 0.060 Uiso 1 1 calc R U . . .
H15B H 0.1815 0.3481 0.2430 0.060 Uiso 1 1 calc R U . . .
C5 C 0.02206(19) 0.2850(5) 0.0664(2) 0.0595(14) Uani 1 1 d . . . . .
H5 H -0.0144 0.2844 0.0562 0.071 Uiso 1 1 calc R U . . .
C25 C 0.07875(19) 0.0186(5) -0.0464(2) 0.0573(13) Uani 1 1 d . . . . .
H25 H 0.0437 0.0015 -0.0593 0.069 Uiso 1 1 calc R U . . .
C29 C 0.16468(19) -0.0152(4) 0.09021(18) 0.0435(11) Uani 1 1 d . . . . .
H29A H 0.1338 -0.0041 0.1126 0.052 Uiso 1 1 calc R U . . .
H29B H 0.1915 0.0459 0.1034 0.052 Uiso 1 1 calc R U . . .
C22 C 0.19222(19) 0.1830(5) -0.14577(19) 0.0521(12) Uani 1 1 d . . . . .
H22 H 0.2179 0.2199 -0.1673 0.063 Uiso 1 1 calc R U . . .
C32 C 0.2581(2) -0.3033(5) 0.0880(2) 0.0579(14) Uani 1 1 d . . . . .
H32A H 0.2913 -0.3182 0.0698 0.069 Uiso 1 1 calc R U . . .
H32B H 0.2653 -0.3128 0.1284 0.069 Uiso 1 1 calc R U . . .
C12 C 0.1083(2) 0.2922(5) 0.3465(2) 0.0603(14) Uani 1 1 d . . . . .
H12A H 0.0731 0.3309 0.3452 0.072 Uiso 1 1 calc R U . . .
H12B H 0.1129 0.2443 0.3813 0.072 Uiso 1 1 calc R U . . .
C31 C 0.23927(19) -0.1689(5) 0.07545(19) 0.0506(12) Uani 1 1 d . . . . .
H31A H 0.2654 -0.1088 0.0912 0.061 Uiso 1 1 calc R U . . .
H31B H 0.2356 -0.1558 0.0350 0.061 Uiso 1 1 calc R U . . .
C35 C 0.1478(2) -0.2486(4) 0.0823(2) 0.0558(13) Uani 1 1 d . . . . .
H35A H 0.1397 -0.2437 0.0419 0.067 Uiso 1 1 calc R U . . .
H35B H 0.1147 -0.2375 0.1010 0.067 Uiso 1 1 calc R U . . .
C24 C 0.1027(2) 0.1093(5) -0.1394(2) 0.0591(14) Uani 1 1 d . . . . .
H24 H 0.0685 0.0959 -0.1555 0.071 Uiso 1 1 calc R U . . .
C11 C 0.1119(2) 0.2038(5) 0.29707(18) 0.0493(12) Uani 1 1 d . . . . .
H11A H 0.1462 0.1607 0.2996 0.059 Uiso 1 1 calc R U . . .
H11B H 0.0841 0.1401 0.2980 0.059 Uiso 1 1 calc R U . . .
C4 C 0.0463(2) 0.3746(5) -0.0270(2) 0.0609(14) Uani 1 1 d . . . . .
H4 H 0.0108 0.3774 -0.0408 0.073 Uiso 1 1 calc R U . . .
C14 C 0.1401(2) 0.4631(5) 0.2957(2) 0.0638(15) Uani 1 1 d . . . . .
H14A H 0.1663 0.5309 0.2962 0.077 Uiso 1 1 calc R U . . .
H14B H 0.1048 0.5012 0.2945 0.077 Uiso 1 1 calc R U . . .
C34 C 0.1721(2) -0.3763(5) 0.0974(2) 0.0637(15) Uani 1 1 d . . . . .
H34A H 0.1800 -0.3808 0.1379 0.076 Uiso 1 1 calc R U . . .
H34B H 0.1468 -0.4430 0.0870 0.076 Uiso 1 1 calc R U . . .
Cl3 Cl 0.25517(6) 0.59763(14) 0.24183(6) 0.0727(4) Uani 1 1 d . . . . .
O5 O 0.3007(2) 0.3475(5) 0.28887(16) 0.0758(12) Uani 1 1 d . . . . .
O6 O 0.4546(3) 0.3265(7) 0.3439(3) 0.165(3) Uani 1 1 d . . . . .
H6O H 0.4548 0.3742 0.3166 0.248 Uiso 1 1 calc R U . . .
Cl1 Cl 0.0000 0.0025(2) 0.2500 0.0717(6) Uani 1 2 d S T P . .
Cl2 Cl 0.0000 0.42160(19) 0.2500 0.0715(6) Uani 1 2 d S T P . .
C36 C 0.4618(4) 0.1947(11) 0.3252(5) 0.184(5) Uani 1 1 d . . . . .
H36A H 0.4529 0.1377 0.3547 0.276 Uiso 1 1 calc R U . . .
H36B H 0.4984 0.1818 0.3165 0.276 Uiso 1 1 calc R U . . .
H36C H 0.4389 0.1788 0.2921 0.276 Uiso 1 1 calc R U . . .
H30 H 0.1924(18) -0.152(4) 0.140(2) 0.055(14) Uiso 1 1 d . . . . .
H5W H 0.284(2) 0.416(5) 0.276(2) 0.067(19) Uiso 1 1 d . . . . .
H5O H 0.281(2) 0.285(6) 0.278(3) 0.08(2) Uiso 1 1 d . . . . .
H10 H 0.0757(18) 0.309(4) 0.2385(18) 0.042(14) 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
Cu1 O1 1.931(3) . ?
Cu1 O11 1.954(3) 7 ?
Cu1 N21 1.967(3) 7 ?
Cu1 N1 1.989(3) . ?
O11 C28 1.318(5) . ?
O11 Cu1 1.954(3) 7 ?
O1 C8 1.314(5) . ?
N1 C2 1.324(5) . ?
N1 C8A 1.372(5) . ?
N21 C22 1.322(5) . ?
N21 C28A 1.361(5) . ?
N21 Cu1 1.967(3) 7 ?
N30 C31 1.490(6) . ?
N30 C35 1.495(6) . ?
N30 C29 1.512(5) . ?
N30 H30 0.95(5) . ?
C7 C8 1.395(6) . ?
C7 C6 1.410(6) . ?
C7 C9 1.502(6) . ?
O13 C12 1.424(6) . ?
O13 C14 1.430(6) . ?
N10 C15 1.494(6) . ?
N10 C11 1.496(6) . ?
N10 C9 1.511(5) . ?
N10 H10 0.84(4) . ?
C28A C24A 1.402(6) . ?
C28A C28 1.436(6) . ?
C28 C27 1.393(6) . ?
O33 C32 1.414(6) . ?
O33 C34 1.419(6) . ?
C27 C26 1.417(6) . ?
C27 C29 1.500(6) . ?
C8A C4A 1.413(6) . ?
C8A C8 1.434(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C24A C24 1.410(7) . ?
C24A C25 1.422(7) . ?
C4A C5 1.411(6) . ?
C4A C4 1.415(7) . ?
C23 C24 1.358(7) . ?
C23 C22 1.398(7) . ?
C23 H23 0.9300 . ?
C3 C4 1.360(7) . ?
C3 C2 1.398(7) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C6 C5 1.366(7) . ?
C6 H6 0.9300 . ?
C26 C25 1.362(7) . ?
C26 H26 0.9300 . ?
C15 C14 1.524(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C5 H5 0.9300 . ?
C25 H25 0.9300 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C22 H22 0.9300 . ?
C32 C31 1.518(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C12 C11 1.506(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C35 C34 1.512(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C24 H24 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 H4 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
O5 H5W 0.89(6) . ?
O5 H5O 0.86(6) . ?
O6 C36 1.473(10) . ?
O6 H6O 0.8200 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O11 179.48(13) . 7 ?
O1 Cu1 N21 95.72(13) . 7 ?
O11 Cu1 N21 84.08(13) 7 7 ?
O1 Cu1 N1 84.24(13) . . ?
O11 Cu1 N1 96.03(13) 7 . ?
N21 Cu1 N1 171.05(14) 7 . ?
C28 O11 Cu1 111.1(2) . 7 ?
C8 O1 Cu1 112.5(2) . . ?
C2 N1 C8A 119.0(4) . . ?
C2 N1 Cu1 130.8(3) . . ?
C8A N1 Cu1 110.2(3) . . ?
C22 N21 C28A 119.0(4) . . ?
C22 N21 Cu1 130.1(3) . 7 ?
C28A N21 Cu1 110.8(3) . 7 ?
C31 N30 C35 110.6(4) . . ?
C31 N30 C29 113.6(3) . . ?
C35 N30 C29 112.7(4) . . ?
C31 N30 H30 108(3) . . ?
C35 N30 H30 108(3) . . ?
C29 N30 H30 104(3) . . ?
C8 C7 C6 119.6(4) . . ?
C8 C7 C9 120.4(4) . . ?
C6 C7 C9 119.8(4) . . ?
C12 O13 C14 109.7(4) . . ?
C15 N10 C11 109.9(4) . . ?
C15 N10 C9 112.0(3) . . ?
C11 N10 C9 110.5(3) . . ?
C15 N10 H10 106(3) . . ?
C11 N10 H10 111(3) . . ?
C9 N10 H10 107(3) . . ?
N21 C28A C24A 122.5(4) . . ?
N21 C28A C28 114.9(4) . . ?
C24A C28A C28 122.6(4) . . ?
O11 C28 C27 124.9(4) . . ?
O11 C28 C28A 117.9(4) . . ?
C27 C28 C28A 117.2(4) . . ?
C32 O33 C34 109.3(4) . . ?
C28 C27 C26 119.7(4) . . ?
C28 C27 C29 119.2(4) . . ?
C26 C27 C29 120.9(4) . . ?
N1 C8A C4A 122.5(4) . . ?
N1 C8A C8 114.8(4) . . ?
C4A C8A C8 122.7(4) . . ?
C7 C9 N10 114.7(4) . . ?
C7 C9 H9A 108.6 . . ?
N10 C9 H9A 108.6 . . ?
C7 C9 H9B 108.6 . . ?
N10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C28A C24A C24 116.9(4) . . ?
C28A C24A C25 118.2(4) . . ?
C24 C24A C25 125.0(5) . . ?
O1 C8 C7 124.8(4) . . ?
O1 C8 C8A 118.1(3) . . ?
C7 C8 C8A 117.1(4) . . ?
C5 C4A C8A 117.9(4) . . ?
C5 C4A C4 126.0(4) . . ?
C8A C4A C4 116.1(4) . . ?
C24 C23 C22 119.8(5) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
N1 C2 C3 122.1(4) . . ?
N1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C5 C6 C7 123.2(4) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C25 C26 C27 122.9(4) . . ?
C25 C26 H26 118.6 . . ?
C27 C26 H26 118.6 . . ?
N10 C15 C14 109.7(4) . . ?
N10 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N10 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C6 C5 C4A 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C4A C5 H5 120.3 . . ?
C26 C25 C24A 119.4(5) . . ?
C26 C25 H25 120.3 . . ?
C24A C25 H25 120.3 . . ?
C27 C29 N30 114.7(3) . . ?
C27 C29 H29A 108.6 . . ?
N30 C29 H29A 108.6 . . ?
C27 C29 H29B 108.6 . . ?
N30 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
N21 C22 C23 121.9(5) . . ?
N21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
O33 C32 C31 112.0(4) . . ?
O33 C32 H32A 109.2 . . ?
C31 C32 H32A 109.2 . . ?
O33 C32 H32B 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
O13 C12 C11 111.2(4) . . ?
O13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
O13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N30 C31 C32 109.7(4) . . ?
N30 C31 H31A 109.7 . . ?
C32 C31 H31A 109.7 . . ?
N30 C31 H31B 109.7 . . ?
C32 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
N30 C35 C34 108.7(4) . . ?
N30 C35 H35A 109.9 . . ?
C34 C35 H35A 109.9 . . ?
N30 C35 H35B 109.9 . . ?
C34 C35 H35B 109.9 . . ?
H35A C35 H35B 108.3 . . ?
C23 C24 C24A 119.9(5) . . ?
C23 C24 H24 120.1 . . ?
C24A C24 H24 120.1 . . ?
N10 C11 C12 110.5(4) . . ?
N10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C3 C4 C4A 120.6(5) . . ?
C3 C4 H4 119.7 . . ?
C4A C4 H4 119.7 . . ?
O13 C14 C15 111.1(4) . . ?
O13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
O13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O33 C34 C35 110.2(4) . . ?
O33 C34 H34A 109.6 . . ?
C35 C34 H34A 109.6 . . ?
O33 C34 H34B 109.6 . . ?
C35 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
H5W O5 H5O 106(5) . . ?
C36 O6 H6O 109.5 . . ?
O6 C36 H36A 109.5 . . ?
O6 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O6 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

_refine_diff_density_max         0.578
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1575108'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
; 
5-chloro-7-{[(2-fluorobenzyl)amino]methyl}quinolin-8-ol
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Cl F N2 O, Cl, H2 O'
_chemical_formula_sum            'C17 H17 Cl2 F N2 O2'
_chemical_formula_weight         371.22

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'
Cl Cl 0.1484 0.1585 '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'

_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                   7.0220(3)
_cell_length_b                   9.4970(5)
_cell_length_c                   13.8230(6)
_cell_angle_alpha                95.430(2)
_cell_angle_beta                 101.7900(10)
_cell_angle_gamma                99.440(2)
_cell_volume                     882.29(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    23627
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.44

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.389
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.5925
_exptl_absorpt_correction_T_max  0.8590
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       RX
_diffrn_measurement_device       RAXIS-RAPID
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           40.0000
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       dtprofit.ref
_diffrn_measurement_details      
;
 scan:  N=1,PHI=90.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                 
 scan:  N=2,PHI=270.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                
 scan:  N=3,PHI=0.0,CHI=0.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                   
 scan:  N=4,PHI=90.0,CHI=0.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                  
 scan:  N=5,PHI=0.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                  
 Orientation Matrix:
    UB11  0.1141 UB12 -0.0073 UB13  0.0548
    UB21  0.0348 UB22  0.1074 UB23  0.0142
    UB31 -0.0879 UB32 -0.0011 UB33  0.0486
    Matrix type: 'd*Trek'
;

_diffrn_reflns_number            34133
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.017
_diffrn_reflns_theta_max         27.436
_diffrn_reflns_theta_full        25.242
_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             4014
_reflns_number_gt                3421
_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       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'Sir2014 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2006)'
_computing_publication_material  'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_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)+(0.0570P)²+0.1551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4014
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
Cl1 Cl 0.85641(6) 0.85200(5) 0.43005(4) 0.06747(15) Uani 1 1 d . . . . .
F1 F 0.41379(16) 0.08822(13) 0.11163(11) 0.0862(4) Uani 1 1 d . . . . .
O1 O 0.11853(17) 0.43225(13) 0.38152(9) 0.0571(3) Uani 1 1 d . . . . .
H1O H 0.055(3) 0.443(2) 0.4223(18) 0.085(7) Uiso 1 1 d . . . . .
N1 N 0.20945(19) 0.65572(14) 0.53693(9) 0.0511(3) Uani 1 1 d . . . . .
N10 N 0.21120(17) 0.41016(12) 0.16353(8) 0.0410(3) Uani 1 1 d . . . . .
H10A H 0.2573 0.4912 0.1415 0.049 Uiso 1 1 calc R U . . .
H10B H 0.1001 0.4211 0.1824 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2560(3) 0.76509(19) 0.60946(12) 0.0580(4) Uani 1 1 d . . . . .
H2 H 0.1704 0.7717 0.6522 0.070 Uiso 1 1 calc R U . . .
C3 C 0.4269(3) 0.87167(18) 0.62555(12) 0.0585(4) Uani 1 1 d . . . . .
H3 H 0.4518 0.9469 0.6773 0.070 Uiso 1 1 calc R U . . .
C4 C 0.5553(2) 0.86429(17) 0.56516(12) 0.0534(4) Uani 1 1 d . . . . .
H4 H 0.6700 0.9338 0.5757 0.064 Uiso 1 1 calc R U . . .
C4A C 0.5139(2) 0.75018(15) 0.48579(10) 0.0454(3) Uani 1 1 d . . . . .
C5 C 0.6364(2) 0.72972(16) 0.41792(11) 0.0482(3) Uani 1 1 d . . . . .
C6 C 0.5878(2) 0.61620(16) 0.34387(11) 0.0478(3) Uani 1 1 d . . . . .
H6 H 0.6719 0.6050 0.3009 0.057 Uiso 1 1 calc R U . . .
C7 C 0.4102(2) 0.51543(15) 0.33205(10) 0.0436(3) Uani 1 1 d . . . . .
C8 C 0.2865(2) 0.53136(15) 0.39571(10) 0.0436(3) Uani 1 1 d . . . . .
C8A C 0.3358(2) 0.64817(15) 0.47445(10) 0.0438(3) Uani 1 1 d . . . . .
C9 C 0.3597(2) 0.38798(15) 0.25202(10) 0.0440(3) Uani 1 1 d . . . . .
H9A H 0.4792 0.3718 0.2314 0.053 Uiso 1 1 calc R U . . .
H9B H 0.3071 0.3029 0.2788 0.053 Uiso 1 1 calc R U . . .
C11 C 0.1632(2) 0.28865(15) 0.07922(11) 0.0495(3) Uani 1 1 d . . . . .
H11A H 0.0572 0.3061 0.0273 0.059 Uiso 1 1 calc R U . . .
H11B H 0.2786 0.2866 0.0511 0.059 Uiso 1 1 calc R U . . .
C12 C 0.1017(2) 0.14474(15) 0.11181(11) 0.0454(3) Uani 1 1 d . . . . .
C13 C 0.2292(2) 0.04892(17) 0.12665(13) 0.0546(4) Uani 1 1 d . . . . .
C14 C 0.1790(3) -0.08427(18) 0.15583(14) 0.0673(5) Uani 1 1 d . . . . .
H14 H 0.2691 -0.1462 0.1645 0.081 Uiso 1 1 calc R U . . .
C15 C -0.0077(3) -0.12282(18) 0.17170(15) 0.0732(5) Uani 1 1 d . . . . .
H15 H -0.0447 -0.2116 0.1924 0.088 Uiso 1 1 calc R U . . .
C16 C -0.1410(3) -0.0315(2) 0.15731(17) 0.0743(5) Uani 1 1 d . . . . .
H16 H -0.2680 -0.0593 0.1674 0.089 Uiso 1 1 calc R U . . .
C17 C -0.0866(3) 0.10146(18) 0.12787(14) 0.0597(4) Uani 1 1 d . . . . .
H17 H -0.1774 0.1628 0.1187 0.072 Uiso 1 1 calc R U . . .
Cl2 Cl 0.78054(6) 0.47363(5) 0.13137(3) 0.06019(14) Uani 1 1 d . . . . .
O2 O 0.4199(2) 0.64003(14) 0.09311(12) 0.0609(3) Uani 1 1 d . . . . .
H2O H 0.527(4) 0.608(3) 0.102(2) 0.101(9) Uiso 1 1 d . . . . .
H2W H 0.374(4) 0.623(3) 0.036(2) 0.084(8) 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
Cl1 C5 1.7416(15) . ?
F1 C13 1.3522(19) . ?
O1 C8 1.3496(18) . ?
O1 H1O 0.80(2) . ?
N1 C2 1.322(2) . ?
N1 C8A 1.364(2) . ?
N10 C9 1.4924(18) . ?
N10 C11 1.5037(17) . ?
N10 H10A 0.8900 . ?
N10 H10B 0.8900 . ?
C2 C3 1.401(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(3) . ?
C3 H3 0.9300 . ?
C4 C4A 1.416(2) . ?
C4 H4 0.9300 . ?
C4A C5 1.417(2) . ?
C4A C8A 1.421(2) . ?
C5 C6 1.362(2) . ?
C6 C7 1.412(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(2) . ?
C7 C9 1.5034(18) . ?
C8 C8A 1.4236(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.503(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.378(2) . ?
C12 C17 1.387(2) . ?
C13 C14 1.377(3) . ?
C14 C15 1.370(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
O2 H2O 0.85(3) . ?
O2 H2W 0.78(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 O1 H1O 114.1(17) . . ?
C2 N1 C8A 117.41(14) . . ?
C9 N10 C11 113.79(11) . . ?
C9 N10 H10A 108.8 . . ?
C11 N10 H10A 108.8 . . ?
C9 N10 H10B 108.8 . . ?
C11 N10 H10B 108.8 . . ?
H10A N10 H10B 107.7 . . ?
N1 C2 C3 123.73(16) . . ?
N1 C2 H2 118.1 . . ?
C3 C2 H2 118.1 . . ?
C4 C3 C2 119.53(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C4A 119.59(15) . . ?
C3 C4 H4 120.2 . . ?
C4A C4 H4 120.2 . . ?
C4 C4A C5 125.13(14) . . ?
C4 C4A C8A 116.92(14) . . ?
C5 C4A C8A 117.96(13) . . ?
C6 C5 C4A 121.83(13) . . ?
C6 C5 Cl1 118.96(12) . . ?
C4A C5 Cl1 119.21(11) . . ?
C5 C6 C7 120.26(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.94(13) . . ?
C8 C7 C9 119.89(12) . . ?
C6 C7 C9 120.14(13) . . ?
O1 C8 C7 117.79(12) . . ?
O1 C8 C8A 121.53(13) . . ?
C7 C8 C8A 120.68(13) . . ?
N1 C8A C4A 122.82(13) . . ?
N1 C8A C8 117.86(13) . . ?
C4A C8A C8 119.32(13) . . ?
N10 C9 C7 111.74(11) . . ?
N10 C9 H9A 109.3 . . ?
C7 C9 H9A 109.3 . . ?
N10 C9 H9B 109.3 . . ?
C7 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C12 C11 N10 112.55(12) . . ?
C12 C11 H11A 109.1 . . ?
N10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
N10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C17 116.70(14) . . ?
C13 C12 C11 121.61(14) . . ?
C17 C12 C11 121.69(14) . . ?
F1 C13 C14 118.32(15) . . ?
F1 C13 C12 118.02(15) . . ?
C14 C13 C12 123.66(16) . . ?
C15 C14 C13 117.97(17) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C16 120.65(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 120.10(18) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.92(17) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
H2O O2 H2W 105(2) . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1575110'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_shelx               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.937 Note
RESPONSE: The collection of the high angle data was limited because of the application of copper wavelength
;
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: This is the consequence of low resolution
;
_vrf_PLAT911_shelx               
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.555        131 Report
RESPONSE: This is the consequence of low resolution
;
# Added during the CSD deposition process: Monday 18 September 2017 01:31 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
; 
bis(7-(piperidin-1-ylmethyl)quinolin-8-ol)-copper(II) dichlorid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H36 Cu N4 O2, 2(Cl)'
_chemical_formula_sum            'C30 H36 Cl2 Cu N4 O2'
_chemical_formula_weight         619.07

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'
Cl Cl 0.3639 0.7018 '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'
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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.5336(2)
_cell_length_b                   10.8906(4)
_cell_length_c                   20.7810(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.408(2)
_cell_angle_gamma                90
_cell_volume                     1478.22(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5907
_cell_measurement_theta_min      7.06
_cell_measurement_theta_max      58.86

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             646
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.973
_shelx_estimated_absorpt_T_min   0.524
_shelx_estimated_absorpt_T_max   0.755
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_T_max  0.9085
_exptl_absorpt_process_details   
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       RX
_diffrn_measurement_device       RAXIS-RAPID

_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       dtprofit.ref
_diffrn_measurement_details      
;
 scan:  N=1,PHI=0.0,CHI=40.0,OMEGA=5.0,185.0,5.0,COUPLE=0.00                   
 scan:  N=2,PHI=90.0,CHI=40.0,OMEGA=38.0,173.0,5.0,COUPLE=0.00                 
 scan:  N=3,PHI=0.0,CHI=0.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                   
 scan:  N=4,PHI=90.0,CHI=0.0,OMEGA=20.0,160.0,5.0,COUPLE=0.00                  
 Orientation Matrix:
    UB11 -0.1271 UB12 -0.0201 UB13  0.0237
    UB21 -0.0002 UB22 -0.0844 UB23 -0.0189
    UB31  0.0854 UB32 -0.0300 UB33  0.0374
    Matrix type: 'd*Trek'
;
_diffrn_reflns_number            10477
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         7.057
_diffrn_reflns_theta_max         58.881
_diffrn_reflns_theta_full        58.881
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.937
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             1982
_reflns_number_gt                1233
_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.

The collection of the high angle data was limited because of the application of
copper wavelength
;

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'Sir2014 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2006)'
_computing_publication_material  'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_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)+(0.0634P)²+7.3639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1982
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.2482
_refine_ls_wR_factor_gt          0.1839
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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
Cl1 Cl 0.0936(4) 0.1769(3) 0.28878(14) 0.0927(10) Uani 1 1 d . . . . .
O1 O 0.6685(9) -0.0448(6) 0.0748(3) 0.0698(18) Uani 1 1 d . . . . .
N1 N 0.6969(12) 0.1327(7) -0.0106(4) 0.067(2) Uani 1 1 d . . . . .
C2 C 0.7067(16) 0.2211(10) -0.0526(5) 0.080(3) Uani 1 1 d . . . . .
H2 H 0.5987 0.2304 -0.0822 0.096 Uiso 1 1 calc R U . . .
Cu2 Cu 0.5000 0.0000 0.0000 0.0739(8) Uani 1 2 d S . P . .
C3 C 0.8709(17) 0.3022(10) -0.0555(5) 0.083(3) Uani 1 1 d . . . . .
H3 H 0.8703 0.3658 -0.0854 0.099 Uiso 1 1 calc R U . . .
C4 C 1.0318(16) 0.2864(10) -0.0138(6) 0.081(3) Uani 1 1 d . . . . .
H4 H 1.1455 0.3373 -0.0166 0.097 Uiso 1 1 calc R U . . .
C4A C 1.0298(15) 0.1946(10) 0.0336(5) 0.068(3) Uani 1 1 d . . . . .
N10 N 0.8926(10) -0.0615(7) 0.2378(4) 0.066(2) Uani 1 1 d . . . . .
H10 H 0.9741 0.0080 0.2539 0.080 Uiso 1 1 calc R U . . .
C5 C 1.1856(16) 0.1726(11) 0.0799(6) 0.079(3) Uani 1 1 d . . . . .
H5 H 1.3035 0.2205 0.0806 0.095 Uiso 1 1 calc R U . . .
C6 C 1.1642(15) 0.0816(11) 0.1237(5) 0.083(3) Uani 1 1 d . . . . .
H6 H 1.2706 0.0686 0.1535 0.100 Uiso 1 1 calc R U . . .
C7 C 0.9913(14) 0.0056(9) 0.1268(4) 0.058(2) Uani 1 1 d . . . . .
C8 C 0.8381(15) 0.0215(10) 0.0800(5) 0.066(3) Uani 1 1 d . . . . .
C8A C 0.8545(16) 0.1206(9) 0.0338(5) 0.066(3) Uani 1 1 d . . . . .
C9 C 0.9751(14) -0.0974(10) 0.1732(5) 0.077(3) Uani 1 1 d . . . . .
H9A H 1.1097 -0.1334 0.1799 0.092 Uiso 1 1 calc R U . . .
H9B H 0.8867 -0.1600 0.1543 0.092 Uiso 1 1 calc R U . . .
C11 C 0.9173(17) -0.1638(10) 0.2852(5) 0.086(3) Uani 1 1 d . . . . .
H11A H 1.0604 -0.1871 0.2888 0.103 Uiso 1 1 calc R U . . .
H11B H 0.8398 -0.2346 0.2703 0.103 Uiso 1 1 calc R U . . .
C12 C 0.8429(17) -0.1246(11) 0.3506(5) 0.095(4) Uani 1 1 d . . . . .
H12A H 0.9257 -0.0569 0.3669 0.114 Uiso 1 1 calc R U . . .
H12B H 0.8566 -0.1923 0.3807 0.114 Uiso 1 1 calc R U . . .
C13 C 0.6199(17) -0.0852(11) 0.3451(6) 0.097(4) Uani 1 1 d . . . . .
H13A H 0.5359 -0.1545 0.3317 0.117 Uiso 1 1 calc R U . . .
H13B H 0.5740 -0.0574 0.3866 0.117 Uiso 1 1 calc R U . . .
C14 C 0.5966(15) 0.0166(10) 0.2968(5) 0.081(3) Uani 1 1 d . . . . .
H14A H 0.6717 0.0879 0.3123 0.097 Uiso 1 1 calc R U . . .
H14B H 0.4532 0.0390 0.2927 0.097 Uiso 1 1 calc R U . . .
C15 C 0.6740(13) -0.0193(9) 0.2313(5) 0.070(3) Uani 1 1 d . . . . .
H15A H 0.5899 -0.0848 0.2133 0.085 Uiso 1 1 calc R U . . .
H15B H 0.6650 0.0505 0.2024 0.085 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
O1 C8 1.324(10) . ?
O1 Cu2 1.945(6) . ?
N1 C2 1.302(12) . ?
N1 C8A 1.373(12) . ?
N1 Cu2 1.951(8) . ?
C2 C3 1.392(13) . ?
C2 H2 0.9300 . ?
Cu2 O1 1.945(6) 3_655 ?
Cu2 N1 1.951(8) 3_655 ?
C3 C4 1.358(13) . ?
C3 H3 0.9300 . ?
C4 C4A 1.403(13) . ?
C4 H4 0.9300 . ?
C4A C8A 1.400(13) . ?
C4A C5 1.405(13) . ?
N10 C11 1.494(11) . ?
N10 C15 1.503(10) . ?
N10 C9 1.510(11) . ?
N10 H10 0.9800 . ?
C5 C6 1.355(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(13) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(12) . ?
C7 C9 1.485(13) . ?
C8 C8A 1.450(13) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.516(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.520(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.500(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.515(12) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 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
C8 O1 Cu2 112.6(6) . . ?
C2 N1 C8A 118.3(9) . . ?
C2 N1 Cu2 131.8(8) . . ?
C8A N1 Cu2 109.8(7) . . ?
N1 C2 C3 123.3(10) . . ?
N1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
O1 Cu2 O1 180.0 3_655 . ?
O1 Cu2 N1 94.9(3) 3_655 . ?
O1 Cu2 N1 85.1(3) . . ?
O1 Cu2 N1 85.1(3) 3_655 3_655 ?
O1 Cu2 N1 94.9(3) . 3_655 ?
N1 Cu2 N1 180.0 . 3_655 ?
C4 C3 C2 118.5(10) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C4A 121.2(10) . . ?
C3 C4 H4 119.4 . . ?
C4A C4 H4 119.4 . . ?
C8A C4A C4 115.8(10) . . ?
C8A C4A C5 118.6(10) . . ?
C4 C4A C5 125.7(10) . . ?
C11 N10 C15 112.0(7) . . ?
C11 N10 C9 111.0(8) . . ?
C15 N10 C9 111.0(7) . . ?
C11 N10 H10 107.5 . . ?
C15 N10 H10 107.5 . . ?
C9 N10 H10 107.5 . . ?
C6 C5 C4A 120.0(10) . . ?
C6 C5 H5 120.0 . . ?
C4A C5 H5 120.0 . . ?
C5 C6 C7 123.9(10) . . ?
C5 C6 H6 118.0 . . ?
C7 C6 H6 118.0 . . ?
C8 C7 C6 117.5(10) . . ?
C8 C7 C9 119.1(9) . . ?
C6 C7 C9 123.0(9) . . ?
O1 C8 C7 125.2(10) . . ?
O1 C8 C8A 115.3(9) . . ?
C7 C8 C8A 119.5(10) . . ?
N1 C8A C4A 122.8(9) . . ?
N1 C8A C8 116.8(9) . . ?
C4A C8A C8 120.3(10) . . ?
C7 C9 N10 114.5(8) . . ?
C7 C9 H9A 108.6 . . ?
N10 C9 H9A 108.6 . . ?
C7 C9 H9B 108.6 . . ?
N10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
N10 C11 C12 110.5(8) . . ?
N10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 109.8(9) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 109.9(9) . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 C15 112.3(9) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
N10 C15 C14 109.6(8) . . ?
N10 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N10 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1575111'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'bis-(5-chloro-7{[(2-fluorobenzyl)amino]methyl}quinolin-8-ol)-aqua-copper(II) zinctetrachlorid methanol solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H32 Cl2 Cu F2 N4 O3, Cl4 Zn, C H4 O'
_chemical_formula_sum            'C36 H36 Cl6 Cu F2 N4 O4 Zn'
_chemical_formula_weight         968.30

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
Cu Cu 0.3201 1.2651 '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                   11.8498(12)
_cell_length_b                   12.9144(11)
_cell_length_c                   14.7891(17)
_cell_angle_alpha                76.700(3)
_cell_angle_beta                 72.214(3)
_cell_angle_gamma                67.890(3)
_cell_volume                     1979.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    35862
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.43

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             982
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.602
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 T.Higashi, Empirical Absorption Correction, 2001
;
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_diffrn_source_current           40.0000
_diffrn_radiation_detector       RX
_diffrn_measurement_device       RAXIS-RAPID
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       dtprofit.ref
_diffrn_measurement_details      
;
 scan:  N=1,PHI=180.0,CHI=0.0,OMEGA=21.0,201.0,5.0,COUPLE=0.00                 
 scan:  N=2,PHI=0.0,CHI=40.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                  
 scan:  N=3,PHI=180.0,CHI=40.0,OMEGA=35.0,215.0,5.0,COUPLE=0.00                
 scan:  N=4,PHI=90.0,CHI=0.0,OMEGA=20.0,200.0,5.0,COUPLE=0.00                  
 Orientation Matrix:
    UB11  0.0200 UB12  0.0030 UB13 -0.0711
    UB21  0.0881 UB22 -0.0499 UB23  0.0001
    UB31 -0.0254 UB32 -0.0679 UB33  0.0084
    Matrix type: 'd*Trek'
;
_diffrn_reflns_number            60741
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.076
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8981
_reflns_number_gt                6884
_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       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'Sir2014 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2006)'
_computing_publication_material  'Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.'
_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)+(0.0383P)²+4.9893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8981
_refine_ls_number_parameters     497
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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
Zn1 Zn 0.31892(4) 0.75194(4) 0.38887(3) 0.02696(12) Uani 1 1 d . . . . .
Cu1 Cu 0.88962(5) 0.64048(4) -0.04716(3) 0.02931(13) Uani 1 1 d . . . . .
Cl4 Cl 0.12909(9) 0.87942(8) 0.37771(7) 0.0320(2) Uani 1 1 d . . . . .
Cl3 Cl 0.35229(9) 0.74085(8) 0.53351(6) 0.0310(2) Uani 1 1 d . . . . .
Cl1 Cl 1.23518(10) 0.99073(9) -0.16020(8) 0.0360(2) Uani 1 1 d . . . . .
Cl2 Cl 0.54104(10) 0.29327(9) 0.07770(8) 0.0402(2) Uani 1 1 d . . . . .
Cl5 Cl 0.46981(9) 0.80988(9) 0.27119(7) 0.0376(2) Uani 1 1 d . . . . .
Cl6 Cl 0.35363(10) 0.57390(8) 0.36357(7) 0.0360(2) Uani 1 1 d . . . . .
O1 O 0.9566(2) 0.7050(2) -0.17777(17) 0.0253(5) Uani 1 1 d . . . . .
O2 O 0.8396(3) 0.5671(2) 0.08231(18) 0.0311(6) Uani 1 1 d . . . . .
F2 F 0.9094(2) 0.42462(19) 0.4137(2) 0.0436(6) Uani 1 1 d . . . . .
N21 N 0.8153(3) 0.5469(3) -0.0835(2) 0.0259(7) Uani 1 1 d . . . . .
O4 O 0.2844(3) 1.0234(3) 0.1790(2) 0.0358(7) Uani 1 1 d . . . . .
O3 O 0.7031(3) 0.7879(3) -0.0489(2) 0.0401(7) Uani 1 1 d . . . . .
N1 N 0.9772(3) 0.7213(3) -0.0082(2) 0.0259(7) Uani 1 1 d . . . . .
C24A C 0.6833(4) 0.4289(3) -0.0084(3) 0.0272(8) Uani 1 1 d . . . . .
C8 C 1.0175(3) 0.7711(3) -0.1761(2) 0.0236(7) Uani 1 1 d . . . . .
N10 N 0.9068(3) 0.8529(3) -0.3384(2) 0.0249(6) Uani 1 1 d . . . . .
H10A H 0.8616 0.9216 -0.3183 0.030 Uiso 1 1 calc R U . . .
H10B H 0.8837 0.7999 -0.2916 0.030 Uiso 1 1 calc R U . . .
C8A C 1.0326(3) 0.7808(3) -0.0859(2) 0.0238(7) Uani 1 1 d . . . . .
F1 F 0.7998(3) 0.6601(2) -0.3880(2) 0.0614(8) Uani 1 1 d . . . . .
C28 C 0.7714(3) 0.5059(3) 0.0848(2) 0.0243(7) Uani 1 1 d . . . . .
C9 C 1.0433(3) 0.8328(3) -0.3512(2) 0.0251(8) Uani 1 1 d . . . . .
H9A H 1.0692 0.8916 -0.4000 0.030 Uiso 1 1 calc R U . . .
H9B H 1.0940 0.7585 -0.3734 0.030 Uiso 1 1 calc R U . . .
C6 C 1.1319(3) 0.9030(3) -0.2501(3) 0.0265(8) Uani 1 1 d . . . . .
H6 H 1.1659 0.9451 -0.3063 0.032 Uiso 1 1 calc R U . . .
N30 N 0.6443(3) 0.5516(3) 0.3079(2) 0.0321(7) Uani 1 1 d . . . . .
H30A H 0.5674 0.5445 0.3199 0.039 Uiso 1 1 calc R U . . .
H30B H 0.6442 0.6158 0.2665 0.039 Uiso 1 1 calc R U . . .
C23 C 0.7369(4) 0.4787(4) -0.1801(3) 0.0352(9) Uani 1 1 d . . . . .
H23 H 0.7322 0.4751 -0.2422 0.042 Uiso 1 1 calc R U . . .
C2 C 0.9838(4) 0.7276(3) 0.0785(3) 0.0288(8) Uani 1 1 d . . . . .
H2 H 0.9442 0.6869 0.1328 0.035 Uiso 1 1 calc R U . . .
C26 C 0.6454(4) 0.3846(3) 0.1639(3) 0.0289(8) Uani 1 1 d . . . . .
H26 H 0.6082 0.3468 0.2216 0.035 Uiso 1 1 calc R U . . .
C7 C 1.0653(3) 0.8359(3) -0.2573(3) 0.0238(7) Uani 1 1 d . . . . .
C3 C 1.0476(4) 0.7927(4) 0.0917(3) 0.0335(9) Uani 1 1 d . . . . .
H3 H 1.0514 0.7953 0.1544 0.040 Uiso 1 1 calc R U . . .
C24 C 0.6750(4) 0.4248(3) -0.1010(3) 0.0320(9) Uani 1 1 d . . . . .
H24 H 0.6263 0.3845 -0.1083 0.038 Uiso 1 1 calc R U . . .
C25 C 0.6279(4) 0.3757(3) 0.0787(3) 0.0305(8) Uani 1 1 d . . . . .
C4A C 1.0976(3) 0.8495(3) -0.0783(3) 0.0263(8) Uani 1 1 d . . . . .
C28A C 0.7544(3) 0.4931(3) -0.0039(3) 0.0257(8) Uani 1 1 d . . . . .
C27 C 0.7174(4) 0.4488(3) 0.1679(3) 0.0271(8) Uani 1 1 d . . . . .
C29 C 0.7402(4) 0.4542(3) 0.2611(3) 0.0273(8) Uani 1 1 d . . . . .
H29A H 0.7387 0.3836 0.3046 0.033 Uiso 1 1 calc R U . . .
H29B H 0.8245 0.4604 0.2490 0.033 Uiso 1 1 calc R U . . .
C4 C 1.1042(4) 0.8524(3) 0.0149(3) 0.0297(8) Uani 1 1 d . . . . .
H4 H 1.1481 0.8960 0.0239 0.036 Uiso 1 1 calc R U . . .
C32 C 0.7704(4) 0.6075(3) 0.3849(3) 0.0305(8) Uani 1 1 d . . . . .
C5 C 1.1486(3) 0.9090(3) -0.1642(3) 0.0261(8) Uani 1 1 d . . . . .
C22 C 0.8070(4) 0.5389(3) -0.1687(3) 0.0321(9) Uani 1 1 d . . . . .
H22 H 0.8501 0.5754 -0.2241 0.038 Uiso 1 1 calc R U . . .
C11 C 0.8745(4) 0.8491(4) -0.4276(3) 0.0318(9) Uani 1 1 d . . . . .
H11A H 0.9295 0.7778 -0.4538 0.038 Uiso 1 1 calc R U . . .
H11B H 0.8894 0.9124 -0.4763 0.038 Uiso 1 1 calc R U . . .
C34 C 0.9863(4) 0.5753(4) 0.3847(3) 0.0366(9) Uani 1 1 d . . . . .
H34 H 1.0658 0.5239 0.3927 0.044 Uiso 1 1 calc R U . . .
C33 C 0.8884(4) 0.5378(3) 0.3936(3) 0.0316(9) Uani 1 1 d . . . . .
C13 C 0.7061(4) 0.7613(4) -0.3870(3) 0.0326(9) Uani 1 1 d . . . . .
C12 C 0.7399(4) 0.8568(4) -0.4069(3) 0.0318(9) Uani 1 1 d . . . . .
C37 C 0.7529(5) 0.7224(4) 0.3639(3) 0.0465(12) Uani 1 1 d . . . . .
H37 H 0.6733 0.7741 0.3566 0.056 Uiso 1 1 calc R U . . .
C31 C 0.6640(4) 0.5640(4) 0.4005(3) 0.0354(9) Uani 1 1 d . . . . .
H31A H 0.5859 0.6163 0.4356 0.042 Uiso 1 1 calc R U . . .
H31B H 0.6813 0.4897 0.4408 0.042 Uiso 1 1 calc R U . . .
C35 C 0.9651(5) 0.6907(4) 0.3637(3) 0.0434(11) Uani 1 1 d . . . . .
H35 H 1.0308 0.7194 0.3565 0.052 Uiso 1 1 calc R U . . .
C14 C 0.5868(5) 0.7597(5) -0.3670(4) 0.0503(12) Uani 1 1 d . . . . .
H14 H 0.5692 0.6912 -0.3552 0.060 Uiso 1 1 calc R U . . .
C36 C 0.8499(6) 0.7625(4) 0.3535(4) 0.0551(14) Uani 1 1 d . . . . .
H36 H 0.8359 0.8413 0.3390 0.066 Uiso 1 1 calc R U . . .
C38 C 0.6164(5) 0.8248(5) 0.0369(4) 0.0577(14) Uani 1 1 d . . . . .
H38A H 0.5958 0.7606 0.0793 0.087 Uiso 1 1 calc R U . . .
H38B H 0.5397 0.8817 0.0219 0.087 Uiso 1 1 calc R U . . .
H38C H 0.6537 0.8577 0.0689 0.087 Uiso 1 1 calc R U . . .
C15 C 0.4943(5) 0.8614(6) -0.3649(6) 0.088(3) Uani 1 1 d . . . . .
H15 H 0.4094 0.8646 -0.3509 0.106 Uiso 1 1 calc R U . . .
C17 C 0.6438(5) 0.9575(5) -0.4058(6) 0.080(2) Uani 1 1 d . . . . .
H17 H 0.6616 1.0262 -0.4210 0.096 Uiso 1 1 calc R U . . .
C16 C 0.5211(6) 0.9596(6) -0.3826(8) 0.127(4) Uani 1 1 d . . . . .
H16 H 0.4546 1.0297 -0.3789 0.153 Uiso 1 1 calc R U . . .
C39 C 0.2424(4) 0.9648(4) 0.1312(3) 0.0397(10) Uani 1 1 d . . . . .
H39A H 0.1904 0.9241 0.1788 0.060 Uiso 1 1 calc R U . . .
H39C H 0.3153 0.9112 0.0942 0.060 Uiso 1 1 calc R U . . .
H39B H 0.1928 1.0193 0.0879 0.060 Uiso 1 1 calc R U . . .
H3O H 0.696(5) 0.854(5) -0.097(4) 0.062(16) Uiso 1 1 d . . . . .
H2O H 0.342(7) 0.977(6) 0.207(5) 0.10(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
Zn1 Cl3 2.2551(10) . ?
Zn1 Cl4 2.2609(10) . ?
Zn1 Cl6 2.2772(11) . ?
Zn1 Cl5 2.3006(11) . ?
Cu1 O2 1.952(3) . ?
Cu1 O1 1.969(2) . ?
Cu1 N21 1.979(3) . ?
Cu1 N1 1.989(3) . ?
Cu1 O3 2.314(3) . ?
Cl1 C5 1.746(4) . ?
Cl2 C25 1.741(4) . ?
O1 C8 1.317(4) . ?
O2 C28 1.315(5) . ?
F2 C33 1.363(5) . ?
N21 C22 1.324(5) . ?
N21 C28A 1.368(5) . ?
O4 C39 1.437(5) . ?
O4 H2O 0.87(7) . ?
O3 C38 1.417(5) . ?
O3 H3O 0.97(6) . ?
N1 C2 1.330(5) . ?
N1 C8A 1.362(5) . ?
C24A C25 1.406(5) . ?
C24A C28A 1.411(5) . ?
C24A C24 1.417(5) . ?
C8 C7 1.394(5) . ?
C8 C8A 1.437(5) . ?
N10 C9 1.496(4) . ?
N10 C11 1.498(5) . ?
N10 H10A 0.9100 . ?
N10 H10B 0.9100 . ?
C8A C4A 1.417(5) . ?
F1 C13 1.360(5) . ?
C28 C27 1.386(5) . ?
C28 C28A 1.440(5) . ?
C9 C7 1.501(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C6 C5 1.367(5) . ?
C6 C7 1.413(5) . ?
C6 H6 0.9500 . ?
N30 C29 1.483(5) . ?
N30 C31 1.508(5) . ?
N30 H30A 0.9100 . ?
N30 H30B 0.9100 . ?
C23 C24 1.369(6) . ?
C23 C22 1.398(6) . ?
C23 H23 0.9500 . ?
C2 C3 1.401(6) . ?
C2 H2 0.9500 . ?
C26 C25 1.375(6) . ?
C26 C27 1.415(6) . ?
C26 H26 0.9500 . ?
C3 C4 1.362(6) . ?
C3 H3 0.9500 . ?
C24 H24 0.9500 . ?
C4A C4 1.413(5) . ?
C4A C5 1.415(5) . ?
C27 C29 1.504(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C4 H4 0.9500 . ?
C32 C33 1.375(6) . ?
C32 C37 1.392(6) . ?
C32 C31 1.502(6) . ?
C22 H22 0.9500 . ?
C11 C12 1.498(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C34 C33 1.378(6) . ?
C34 C35 1.391(6) . ?
C34 H34 0.9500 . ?
C13 C14 1.360(6) . ?
C13 C12 1.379(6) . ?
C12 C17 1.368(7) . ?
C37 C36 1.384(7) . ?
C37 H37 0.9500 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C35 C36 1.362(7) . ?
C35 H35 0.9500 . ?
C14 C15 1.357(8) . ?
C14 H14 0.9500 . ?
C36 H36 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C15 C16 1.370(10) . ?
C15 H15 0.9500 . ?
C17 C16 1.379(8) . ?
C17 H17 0.9500 . ?
C16 H16 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39C 0.9800 . ?
C39 H39B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl3 Zn1 Cl4 110.51(4) . . ?
Cl3 Zn1 Cl6 107.78(4) . . ?
Cl4 Zn1 Cl6 116.10(4) . . ?
Cl3 Zn1 Cl5 109.41(4) . . ?
Cl4 Zn1 Cl5 108.04(4) . . ?
Cl6 Zn1 Cl5 104.73(4) . . ?
O2 Cu1 O1 174.54(12) . . ?
O2 Cu1 N21 84.22(12) . . ?
O1 Cu1 N21 97.09(11) . . ?
O2 Cu1 N1 93.95(12) . . ?
O1 Cu1 N1 84.27(11) . . ?
N21 Cu1 N1 174.61(13) . . ?
O2 Cu1 O3 97.94(11) . . ?
O1 Cu1 O3 87.42(11) . . ?
N21 Cu1 O3 87.81(12) . . ?
N1 Cu1 O3 97.48(12) . . ?
C8 O1 Cu1 110.8(2) . . ?
C28 O2 Cu1 111.2(2) . . ?
C22 N21 C28A 118.8(3) . . ?
C22 N21 Cu1 130.1(3) . . ?
C28A N21 Cu1 110.7(2) . . ?
C39 O4 H2O 112(5) . . ?
C38 O3 Cu1 121.6(3) . . ?
C38 O3 H3O 107(3) . . ?
Cu1 O3 H3O 123(3) . . ?
C2 N1 C8A 119.2(3) . . ?
C2 N1 Cu1 130.1(3) . . ?
C8A N1 Cu1 110.6(2) . . ?
C25 C24A C28A 117.2(3) . . ?
C25 C24A C24 126.6(4) . . ?
C28A C24A C24 116.2(3) . . ?
O1 C8 C7 123.4(3) . . ?
O1 C8 C8A 119.0(3) . . ?
C7 C8 C8A 117.5(3) . . ?
C9 N10 C11 113.6(3) . . ?
C9 N10 H10A 108.8 . . ?
C11 N10 H10A 108.8 . . ?
C9 N10 H10B 108.8 . . ?
C11 N10 H10B 108.8 . . ?
H10A N10 H10B 107.7 . . ?
N1 C8A C4A 122.5(3) . . ?
N1 C8A C8 115.1(3) . . ?
C4A C8A C8 122.4(3) . . ?
O2 C28 C27 124.0(3) . . ?
O2 C28 C28A 118.8(3) . . ?
C27 C28 C28A 117.1(3) . . ?
N10 C9 C7 109.0(3) . . ?
N10 C9 H9A 109.9 . . ?
C7 C9 H9A 109.9 . . ?
N10 C9 H9B 109.9 . . ?
C7 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C29 N30 C31 114.4(3) . . ?
C29 N30 H30A 108.7 . . ?
C31 N30 H30A 108.7 . . ?
C29 N30 H30B 108.7 . . ?
C31 N30 H30B 108.7 . . ?
H30A N30 H30B 107.6 . . ?
C24 C23 C22 119.6(4) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
N1 C2 C3 121.7(4) . . ?
N1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C25 C26 C27 121.7(3) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 C9 118.4(3) . . ?
C6 C7 C9 121.5(3) . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C23 C24 C24A 120.1(4) . . ?
C23 C24 H24 119.9 . . ?
C24A C24 H24 119.9 . . ?
C26 C25 C24A 120.8(4) . . ?
C26 C25 Cl2 119.8(3) . . ?
C24A C25 Cl2 119.4(3) . . ?
C4 C4A C5 126.4(4) . . ?
C4 C4A C8A 116.6(3) . . ?
C5 C4A C8A 117.0(3) . . ?
N21 C28A C24A 122.9(3) . . ?
N21 C28A C28 114.2(3) . . ?
C24A C28A C28 122.9(3) . . ?
C28 C27 C26 120.2(3) . . ?
C28 C27 C29 118.5(3) . . ?
C26 C27 C29 121.3(3) . . ?
N30 C29 C27 111.6(3) . . ?
N30 C29 H29A 109.3 . . ?
C27 C29 H29A 109.3 . . ?
N30 C29 H29B 109.3 . . ?
C27 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
C3 C4 C4A 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C4A C4 H4 120.0 . . ?
C33 C32 C37 116.2(4) . . ?
C33 C32 C31 122.5(4) . . ?
C37 C32 C31 121.2(4) . . ?
C6 C5 C4A 121.1(3) . . ?
C6 C5 Cl1 119.6(3) . . ?
C4A C5 Cl1 119.3(3) . . ?
N21 C22 C23 122.3(4) . . ?
N21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
N10 C11 C12 110.6(3) . . ?
N10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C33 C34 C35 117.9(4) . . ?
C33 C34 H34 121.1 . . ?
C35 C34 H34 121.1 . . ?
F2 C33 C32 118.0(4) . . ?
F2 C33 C34 117.9(4) . . ?
C32 C33 C34 124.1(4) . . ?
F1 C13 C14 117.1(4) . . ?
F1 C13 C12 117.4(4) . . ?
C14 C13 C12 125.5(4) . . ?
C17 C12 C13 116.1(4) . . ?
C17 C12 C11 122.7(4) . . ?
C13 C12 C11 121.2(4) . . ?
C36 C37 C32 121.0(5) . . ?
C36 C37 H37 119.5 . . ?
C32 C37 H37 119.5 . . ?
C32 C31 N30 112.6(3) . . ?
C32 C31 H31A 109.1 . . ?
N30 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
N30 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C36 C35 C34 119.8(5) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C15 C14 C13 116.3(5) . . ?
C15 C14 H14 121.8 . . ?
C13 C14 H14 121.8 . . ?
C35 C36 C37 121.0(4) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
O3 C38 H38A 109.5 . . ?
O3 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O3 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C14 C15 C16 121.2(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C12 C17 C16 120.2(6) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C15 C16 C17 120.5(6) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
O4 C39 H39A 109.5 . . ?
O4 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
O4 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39C C39 H39B 109.5 . . ?

_refine_diff_density_max         0.738
_refine_diff_density_min         -0.963
_refine_diff_density_rms         0.126

