# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Enamullah_CoL48R
_database_code_depnum_ccdc_archive 'CCDC 2060528'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
2-{(E)-((R)-1-(phenyl)ethylimino)(phenyl)methyl}phenol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N O'
_chemical_formula_sum            'C21 H19 N O'
_chemical_formula_weight         301.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   9.9056(5)
_cell_length_b                   8.1390(4)
_cell_length_c                   10.8874(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.182(2)
_cell_angle_gamma                90
_cell_volume                     818.46(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      4.355
_cell_measurement_theta_max      67.585

_exptl_crystal_description       block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             320
_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    0.581
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8925
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22837
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.355
_diffrn_reflns_theta_max         67.819
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2955
_reflns_number_gt                2913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.991

_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       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4.3.1 (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'

_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.1002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2955
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35734(12) 0.22569(15) 0.16066(12) 0.0329(3) Uani 1 1 d . . . . .
C1 C 0.48895(17) 0.2196(2) 0.15078(15) 0.0267(3) Uani 1 1 d . . . . .
H1 H 0.359(2) 0.313(3) 0.212(2) 0.040 Uiso 1 1 d . U . . .
N1 N 0.44353(13) 0.48213(17) 0.29865(12) 0.0264(3) Uani 1 1 d . . . . .
C6 C 0.59830(17) 0.3358(2) 0.21455(14) 0.0246(3) Uani 1 1 d . . . . .
C2 C 0.51580(19) 0.0961(2) 0.07385(17) 0.0332(4) Uani 1 1 d . . . . .
H2 H 0.443137 0.016819 0.032701 0.040 Uiso 1 1 calc R U . . .
C5 C 0.73131(17) 0.3220(2) 0.19704(15) 0.0285(3) Uani 1 1 d . . . . .
H5 H 0.806491 0.397716 0.240278 0.034 Uiso 1 1 calc R U . . .
C3 C 0.64693(19) 0.0884(2) 0.05707(17) 0.0355(4) Uani 1 1 d . . . . .
H3 H 0.663173 0.005062 0.002892 0.043 Uiso 1 1 calc R U . . .
C4 C 0.75575(18) 0.2012(2) 0.11853(16) 0.0334(4) Uani 1 1 d . . . . .
H4 H 0.846035 0.195153 0.106648 0.040 Uiso 1 1 calc R U . . .
C8 C 0.69063(16) 0.58957(19) 0.35950(16) 0.0255(3) Uani 1 1 d . . . . .
C7 C 0.57033(16) 0.4714(2) 0.29182(14) 0.0244(3) Uani 1 1 d . . . . .
C9 C 0.77344(17) 0.5662(2) 0.49214(16) 0.0307(4) Uani 1 1 d . . . . .
H9 H 0.753466 0.476349 0.538672 0.037 Uiso 1 1 calc R U . . .
C10 C 0.88532(18) 0.6742(2) 0.55644(17) 0.0350(4) Uani 1 1 d . . . . .
H10 H 0.941725 0.658044 0.646934 0.042 Uiso 1 1 calc R U . . .
C11 C 0.91483(19) 0.8049(2) 0.48945(18) 0.0377(4) Uani 1 1 d . . . . .
H11 H 0.991812 0.878093 0.533586 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8322(2) 0.8292(2) 0.35801(19) 0.0398(4) Uani 1 1 d . . . . .
H12 H 0.852048 0.919718 0.312067 0.048 Uiso 1 1 calc R U . . .
C13 C 0.72048(19) 0.7218(2) 0.29298(17) 0.0342(4) Uani 1 1 d . . . . .
H13 H 0.664180 0.738888 0.202574 0.041 Uiso 1 1 calc R U . . .
C14 C 0.40297(17) 0.6204(2) 0.36501(16) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.478696 0.707837 0.383474 0.034 Uiso 1 1 calc R U . . .
C15 C 0.25984(16) 0.6887(2) 0.27159(15) 0.0263(3) Uani 1 1 d . . . . .
C16 C 0.25283(19) 0.8463(2) 0.22279(16) 0.0316(4) Uani 1 1 d . . . . .
H16 H 0.338336 0.910951 0.247011 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1229(2) 0.9118(2) 0.13893(18) 0.0403(4) Uani 1 1 d . . . . .
H17 H 0.119430 1.021231 0.107664 0.048 Uiso 1 1 calc R U . . .
C18 C -0.0012(2) 0.8179(3) 0.10107(18) 0.0411(5) Uani 1 1 d . . . . .
H18 H -0.090065 0.861819 0.042658 0.049 Uiso 1 1 calc R U . . .
C19 C 0.00425(19) 0.6596(3) 0.14847(18) 0.0412(5) Uani 1 1 d . . . . .
H19 H -0.081227 0.594742 0.122810 0.049 Uiso 1 1 calc R U . . .
C20 C 0.13382(18) 0.5950(2) 0.23323(18) 0.0352(4) Uani 1 1 d . . . . .
H20 H 0.136676 0.486063 0.265397 0.042 Uiso 1 1 calc R U . . .
C21 C 0.3948(2) 0.5614(3) 0.49506(17) 0.0394(4) Uani 1 1 d . . . . .
H21A H 0.331508 0.464985 0.479128 0.059 Uiso 1 1 calc R U . . .
H21B H 0.355719 0.649293 0.533995 0.059 Uiso 1 1 calc R U . . .
H21C H 0.492008 0.531906 0.555628 0.059 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 C1 1.347(2) . ?
O1 H1 0.90(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.417(2) . ?
N1 C7 1.288(2) . ?
N1 C14 1.470(2) . ?
C6 C5 1.402(2) . ?
C6 C7 1.473(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C5 C4 1.381(2) . ?
C5 H5 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C8 C13 1.388(2) . ?
C8 C9 1.392(2) . ?
C8 C7 1.501(2) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.520(2) . ?
C14 C21 1.525(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.381(3) . ?
C15 C20 1.392(2) . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C1 O1 H1 106.1(13) . . ?
O1 C1 C2 118.36(15) . . ?
O1 C1 C6 121.78(14) . . ?
C2 C1 C6 119.86(14) . . ?
C7 N1 C14 121.72(13) . . ?
C5 C6 C1 118.00(15) . . ?
C5 C6 C7 121.15(14) . . ?
C1 C6 C7 120.79(13) . . ?
C3 C2 C1 120.44(16) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C5 C6 121.65(16) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C2 C3 C4 120.72(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.31(15) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C13 C8 C9 119.39(15) . . ?
C13 C8 C7 121.46(14) . . ?
C9 C8 C7 119.15(14) . . ?
N1 C7 C6 118.18(14) . . ?
N1 C7 C8 123.10(14) . . ?
C6 C7 C8 118.72(13) . . ?
C10 C9 C8 119.97(16) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.30(16) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.90(16) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.20(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.24(16) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
N1 C14 C15 107.78(13) . . ?
N1 C14 C21 109.30(14) . . ?
C15 C14 C21 112.77(13) . . ?
N1 C14 H14 109.0 . . ?
C15 C14 H14 109.0 . . ?
C21 C14 H14 109.0 . . ?
C16 C15 C20 118.59(15) . . ?
C16 C15 C14 120.13(14) . . ?
C20 C15 C14 121.28(15) . . ?
C15 C16 C17 121.04(16) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.95(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.68(17) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.28(17) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.44(17) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.90(2) 1.71(2) 2.5328(18) 151(2) . yes

_refine_diff_density_max         0.098
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.028



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_CuL48R
_database_code_depnum_ccdc_archive 'CCDC 2060529'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        bis[2-oxo-benzophenonato-\kO,O']-copper(II)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18.88 Cu N0.88 O3.12'
_chemical_formula_sum            'C26 H18.88 Cu N0.88 O3.12'
_chemical_formula_weight         457.08

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'
O O 0.0106 0.0060 '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'

_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                   18.4742(15)
_cell_length_b                   5.8299(5)
_cell_length_c                   19.8803(17)
_cell_angle_alpha                90
_cell_angle_beta                 113.803(4)
_cell_angle_gamma                90
_cell_volume                     1959.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    3429
_cell_measurement_theta_min      2.543
_cell_measurement_theta_max      27.604

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear black'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_F_000             940
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    1.145
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9081
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10309
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.239
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2278
_reflns_number_gt                1928
_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       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4.3.1 (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'

_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+2.8120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2278
_refine_ls_number_parameters     150
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.500000 1.000000 0.500000 0.02213(15) Uani 1 2 d S . P . .
O1 O 0.48243(9) 0.7706(3) 0.42669(8) 0.0250(4) Uani 1 1 d . . . . .
C1 C 0.52868(12) 0.5993(4) 0.42792(11) 0.0202(4) Uani 1 1 d . . . . .
O2 O 0.5986(7) 0.8646(18) 0.5584(6) 0.0269(18) Uani 0.56(3) 1 d . . P A 1
N1 N 0.6063(10) 0.893(3) 0.5639(9) 0.020(2) Uiso 0.44(3) 1 d D . P A 2
H1 H 0.627(4) 0.941(11) 0.6102(19) 0.030 Uiso 0.44(3) 1 d D U P A 2
C2 C 0.50256(13) 0.4485(4) 0.36691(12) 0.0254(5) Uani 1 1 d . . . . .
H2A H 0.453063 0.476318 0.327231 0.030 Uiso 1 1 calc R U . . .
C3 C 0.54679(13) 0.2630(4) 0.36349(12) 0.0261(5) Uani 1 1 d . . . . .
H3 H 0.527208 0.164939 0.321798 0.031 Uiso 1 1 calc R U . . .
C4 C 0.62044(13) 0.2161(4) 0.42062(12) 0.0243(5) Uani 1 1 d . . . . .
H4 H 0.650796 0.087478 0.418034 0.029 Uiso 1 1 calc R U . . .
C5 C 0.64757(12) 0.3595(4) 0.48011(11) 0.0216(5) Uani 1 1 d . . . . .
H5 H 0.697704 0.329265 0.518609 0.026 Uiso 1 1 calc R U . . .
C6 C 0.60368(12) 0.5516(4) 0.48649(11) 0.0189(4) Uani 1 1 d . . . . .
C7 C 0.63569(11) 0.6943(4) 0.55141(11) 0.0185(4) Uani 1 1 d . . . . .
C8 C 0.71294(11) 0.6365(4) 0.61322(10) 0.0182(4) Uani 1 1 d . . . . .
C9 C 0.72143(13) 0.4388(4) 0.65497(12) 0.0217(5) Uani 1 1 d . . . . .
H9 H 0.679740 0.329766 0.641662 0.026 Uiso 1 1 calc R U . . .
C10 C 0.79163(13) 0.4021(5) 0.71650(12) 0.0263(5) Uani 1 1 d . . . . .
H10 H 0.797607 0.268312 0.745562 0.032 Uiso 1 1 calc R U . . .
C11 C 0.85290(13) 0.5605(5) 0.73547(12) 0.0280(5) Uani 1 1 d . . . . .
H11 H 0.900432 0.535435 0.777717 0.034 Uiso 1 1 calc R U . . .
C12 C 0.84485(13) 0.7549(5) 0.69293(12) 0.0281(5) Uani 1 1 d . . . . .
H12 H 0.887247 0.861243 0.705309 0.034 Uiso 1 1 calc R U . . .
C13 C 0.77455(13) 0.7940(4) 0.63207(12) 0.0237(5) Uani 1 1 d . . . . .
H13 H 0.768584 0.928528 0.603338 0.028 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 O2 1.892(11) 5_676 ?
Cu1 O2 1.892(11) . ?
Cu1 O1 1.9070(16) . ?
Cu1 O1 1.9071(16) 5_676 ?
Cu1 N1 1.961(18) . ?
Cu1 N1 1.961(18) 5_676 ?
O1 C1 1.308(3) . ?
C1 C2 1.416(3) . ?
C1 C6 1.432(3) . ?
O2 C7 1.246(11) . ?
N1 C7 1.343(19) . ?
N1 H1 0.89(2) . ?
C2 C3 1.373(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.403(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.418(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.446(3) . ?
C7 C8 1.498(3) . ?
C8 C13 1.391(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
O2 Cu1 O2 180.0 5_676 . ?
O2 Cu1 O1 89.9(3) 5_676 . ?
O2 Cu1 O1 90.1(3) . . ?
O2 Cu1 O1 90.1(3) 5_676 5_676 ?
O2 Cu1 O1 89.9(3) . 5_676 ?
O1 Cu1 O1 180.00(7) . 5_676 ?
O1 Cu1 N1 95.1(5) . . ?
O1 Cu1 N1 84.9(5) 5_676 . ?
O2 Cu1 N1 6.1(7) 5_676 5_676 ?
O2 Cu1 N1 173.9(7) . 5_676 ?
O1 Cu1 N1 84.9(5) . 5_676 ?
O1 Cu1 N1 95.1(5) 5_676 5_676 ?
N1 Cu1 N1 180.0(7) . 5_676 ?
C1 O1 Cu1 127.79(13) . . ?
O1 C1 C2 117.64(18) . . ?
O1 C1 C6 125.0(2) . . ?
C2 C1 C6 117.3(2) . . ?
C7 O2 Cu1 134.5(7) . . ?
C7 N1 Cu1 121.9(11) . . ?
C7 N1 H1 115(5) . . ?
Cu1 N1 H1 118(5) . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2A 119.1 . . ?
C1 C2 H2A 119.1 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 122.47(19) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 119.44(18) . . ?
C1 C6 C7 121.8(2) . . ?
O2 C7 C6 120.8(5) . . ?
N1 C7 C6 127.6(7) . . ?
O2 C7 C8 118.2(5) . . ?
N1 C7 C8 111.4(7) . . ?
C6 C7 C8 120.90(19) . . ?
C13 C8 C9 120.21(19) . . ?
C13 C8 C7 118.51(19) . . ?
C9 C8 C7 121.09(19) . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.084



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/dichloromethane'
