# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ZJNU-11
_database_code_depnum_ccdc_archive 'CCDC 1921552'
loop_
_audit_author_name
_audit_author_address
'Yabing He'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2019-06-07 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Cu2 N O10'
_chemical_formula_weight         594.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'

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

_cell_length_a                   18.5626(7)
_cell_length_b                   18.5626(7)
_cell_length_c                   23.7453(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7085.7(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    24253
_cell_measurement_theta_min      3
_cell_measurement_theta_max      65

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.836
_exptl_crystal_F_000             1800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.374
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.875
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24310
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.320
_diffrn_reflns_theta_max         65.197
_diffrn_reflns_theta_full        65.197
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2272
_reflns_number_gt                1690
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2272
_refine_ls_number_parameters     107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.2745
_refine_ls_wR_factor_gt          0.2631
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.098
_refine_ls_shift/su_mean         0.016

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.04724(4) 0.52362(2) 0.95385(3) 0.0980(5) Uani 1 2 d S T P . .
O1 O 0.97027(18) 0.5599(2) 0.92882(13) 0.1133(10) Uani 1 1 d . . . . .
O1W O 1.1158(5) 0.5579(2) 0.8765(3) 0.185(3) Uani 1 2 d S T P . .
H1WA H 1.1545 0.5491 0.8798 0.222 Uiso 1 1 d R U . . .
O2 O 0.88879(18) 0.5171(2) 1.00637(13) 0.1201(11) Uani 1 1 d . . . . .
N1 N 0.8106(8) 0.5618(8) 0.7500 0.132(5) Uani 0.5 2 d S T P . .
H1A H 0.8176 0.5403 0.7821 0.158 Uiso 0.25 1 d R U P . .
C1 C 0.9086(3) 0.5495(3) 0.9575(2) 0.1085(14) Uani 1 1 d . . . . .
C2 C 0.8529(2) 0.5764(3) 0.93166(18) 0.1070(13) Uani 1 1 d . . . . .
C3 C 0.7786(2) 0.5571(4) 0.9570(2) 0.1034(16) Uani 1 2 d S T P . .
H3A H 0.7650 0.5300 0.9925 0.124 Uiso 1 2 calc R U P . .
C4 C 0.8748(3) 0.6217(3) 0.88133(18) 0.1094(13) Uani 1 1 d . . . . .
H4A H 0.9267 0.6369 0.8643 0.131 Uiso 1 1 calc R U . . .
C5 C 0.8225(2) 0.6450(4) 0.8559(2) 0.1033(16) Uani 1 2 d S T P . .
C6 C 0.8445(2) 0.6889(4) 0.8010(3) 0.1111(17) Uani 1 2 d S T P . .
C7 C 0.8536(6) 0.7700(6) 0.7998(4) 0.124(3) Uani 0.5 1 d . . P . .
H7A H 0.8498 0.7948 0.8342 0.149 Uiso 0.5 1 d R U P . .
C8 C 0.8605(11) 0.8091(11) 0.7500 0.164(7) Uani 0.5 2 d S T P . .
C9 C 0.8573(19) 0.8886(14) 0.7500 0.282(17) Uani 0.5 2 d S T P . .
H9A H 0.8631 0.9093 0.7113 0.423 Uiso 0.25 1 calc R U P . .
H9B H 0.8040 0.8780 0.7655 0.423 Uiso 0.25 1 calc R U P . .
H9C H 0.9028 0.9304 0.7731 0.423 Uiso 0.25 1 calc R U P . .
C10 C 0.8244(3) 0.6488(6) 0.7500 0.103(2) Uani 1 4 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.942(3) 9_767 ?
Cu1 O2 1.942(3) 13_767 ?
Cu1 O1 1.952(3) . ?
Cu1 O1 1.952(3) 21 ?
Cu1 O1W 2.142(6) . ?
Cu1 Cu1 2.6664(15) 13_767 ?
O1 C1 1.260(5) . ?
O1W H1WA 0.8158 . ?
O2 C1 1.274(6) . ?
O2 Cu1 1.942(3) 13_767 ?
N1 N1 1.10(2) 20_655 ?
N1 C10 1.502(14) . ?
N1 H1A 0.9001 . ?
C1 C2 1.488(6) . ?
C2 C3 1.377(5) . ?
C2 C4 1.400(7) . ?
C3 C2 1.377(5) 20_655 ?
C3 H3A 0.9500 . ?
C4 C5 1.382(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.483(9) . ?
C5 C4 1.382(5) 20_655 ?
C6 C10 1.373(8) . ?
C6 C7 1.428(11) . ?
C6 C7 1.428(11) 20_655 ?
C7 C7 1.165(19) 20_655 ?
C7 C8 1.360(12) . ?
C7 C8 1.937(15) 20_655 ?
C7 H7A 0.9558 . ?
C8 C7 1.360(12) 16_557 ?
C8 C9 1.51(2) . ?
C8 C8 1.63(3) 20_655 ?
C8 C7 1.937(15) 20_655 ?
C8 C7 1.937(15) 11_656 ?
C9 C9 1.49(4) 21_565 ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C6 1.373(8) 16_557 ?
C10 N1 1.502(14) 20_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 88.0(2) 9_767 13_767 ?
O2 Cu1 O1 89.40(15) 9_767 . ?
O2 Cu1 O1 167.93(14) 13_767 . ?
O2 Cu1 O1 167.92(14) 9_767 21 ?
O2 Cu1 O1 89.40(15) 13_767 21 ?
O1 Cu1 O1 90.6(2) . 21 ?
O2 Cu1 O1W 98.33(19) 9_767 . ?
O2 Cu1 O1W 98.31(19) 13_767 . ?
O1 Cu1 O1W 93.73(19) . . ?
O1 Cu1 O1W 93.72(19) 21 . ?
O2 Cu1 Cu1 84.37(10) 9_767 13_767 ?
O2 Cu1 Cu1 84.37(10) 13_767 13_767 ?
O1 Cu1 Cu1 83.64(10) . 13_767 ?
O1 Cu1 Cu1 83.64(10) 21 13_767 ?
O1W Cu1 Cu1 176.2(2) . 13_767 ?
C1 O1 Cu1 123.2(3) . . ?
Cu1 O1W H1WA 108.0 . . ?
C1 O2 Cu1 122.6(3) . 13_767 ?
N1 N1 C10 68.5(5) 20_655 . ?
N1 N1 H1A 111.5 20_655 . ?
C10 N1 H1A 119.5 . . ?
O1 C1 O2 126.1(4) . . ?
O1 C1 C2 117.2(4) . . ?
O2 C1 C2 116.7(4) . . ?
C3 C2 C4 118.7(4) . . ?
C3 C2 C1 120.5(5) . . ?
C4 C2 C1 120.8(4) . . ?
C2 C3 C2 121.2(6) . 20_655 ?
C2 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 20_655 . ?
C2 C4 C5 121.5(4) . . ?
C2 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 C4 120.9(3) . 20_655 ?
C4 C5 C4 118.2(6) . 20_655 ?
C10 C6 C5 123.5(7) . . ?
C10 C6 C7 114.3(7) . . ?
C5 C6 C7 116.9(7) . . ?
C10 C6 C7 114.3(7) . 20_655 ?
C5 C6 C7 116.9(7) . 20_655 ?
C7 C6 C7 48.2(8) . 20_655 ?
C7 C7 C8 99.9(9) 20_655 . ?
C7 C7 C6 65.9(4) 20_655 . ?
C8 C7 C6 120.7(11) . . ?
C7 C7 C8 43.7(5) 20_655 20_655 ?
C8 C7 C8 56.2(12) . 20_655 ?
C6 C7 C8 90.8(7) . 20_655 ?
C7 C7 H7A 108.3 20_655 . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.4 . . ?
C8 C7 H7A 127.8 20_655 . ?
C7 C8 C7 120.9(16) . 16_557 ?
C7 C8 C9 118.9(8) . . ?
C7 C8 C9 118.9(8) 16_557 . ?
C7 C8 C8 80.1(9) . 20_655 ?
C7 C8 C8 80.1(9) 16_557 20_655 ?
C9 C8 C8 122.0(14) . 20_655 ?
C7 C8 C7 36.3(7) . 20_655 ?
C7 C8 C7 104.8(13) 16_557 20_655 ?
C9 C8 C7 131.1(11) . 20_655 ?
C8 C8 C7 43.7(5) 20_655 20_655 ?
C7 C8 C7 104.8(13) . 11_656 ?
C7 C8 C7 36.3(7) 16_557 11_656 ?
C9 C8 C7 131.1(11) . 11_656 ?
C8 C8 C7 43.7(5) 20_655 11_656 ?
C7 C8 C7 75.2(9) 20_655 11_656 ?
C8 C9 C9 178.0(13) . 21_565 ?
C8 C9 H9A 109.5 . . ?
C9 C9 H9A 70.3 21_565 . ?
C8 C9 H9B 109.5 . . ?
C9 C9 H9B 72.3 21_565 . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.4 . . ?
C9 C9 H9C 69.0 21_565 . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C6 123.9(9) . 16_557 ?
C6 C10 N1 115.9(4) . 20_655 ?
C6 C10 N1 115.9(4) 16_557 20_655 ?
C6 C10 N1 115.9(4) . . ?
C6 C10 N1 115.9(4) 16_557 . ?
N1 C10 N1 43.0(10) 20_655 . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_ZJNU-12
_database_code_depnum_ccdc_archive 'CCDC 1921553'
loop_
_audit_author_name
_audit_author_address
'Yabing He'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2019-06-07 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Cu2 N O10'
_chemical_formula_weight         594.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'

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

_cell_length_a                   18.6231(7)
_cell_length_b                   18.6231(7)
_cell_length_c                   23.8591(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7166.2(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    35611
_cell_measurement_theta_min      6
_cell_measurement_theta_max      68

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.826
_exptl_crystal_F_000             1800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.359
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53611
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.1458
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         5.791
_diffrn_reflns_theta_max         68.181
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2464
_reflns_number_gt                1838
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     107
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.2016
_refine_ls_wR_factor_gt          0.1705
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.003
_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 1.04704(3) 0.52352(2) 0.95434(2) 0.0226(3) Uani 1 2 d S T P . .
O1 O 0.97031(15) 0.56036(18) 0.92919(10) 0.0511(7) Uani 1 1 d . . . . .
O1W O 1.1170(4) 0.55848(19) 0.8791(2) 0.0985(18) Uani 1 2 d S T P . .
H1WA H 1.1556 0.5491 0.8825 0.118 Uiso 1 1 d R U . . .
O2 O 0.88923(15) 0.51825(17) 1.00595(10) 0.0513(7) Uani 1 1 d . . . . .
N1 N 0.8557(10) 0.8886(7) 0.7500 0.135(6) Uani 0.5 2 d S T P . .
H1A H 0.8530 0.9115 0.7826 0.162 Uiso 0.25 1 d R U P . .
H1B H 0.8597 0.9147 0.7174 0.162 Uiso 0.25 1 d R U P . .
C1 C 0.9092(2) 0.5506(2) 0.95780(14) 0.0413(8) Uani 1 1 d . U . . .
C2 C 0.8536(2) 0.5780(2) 0.93178(14) 0.0406(8) Uani 1 1 d . U . . .
C3 C 0.77850(16) 0.5570(3) 0.95742(18) 0.0400(11) Uani 1 2 d S TU P . .
H3A H 0.7642 0.5284 0.9922 0.048 Uiso 1 2 calc R U P . .
C4 C 0.8744(2) 0.6201(2) 0.88104(14) 0.0443(9) Uani 1 1 d . U . . .
H4A H 0.9255 0.6339 0.8636 0.053 Uiso 1 1 calc R U . . .
C5 C 0.82109(17) 0.6422(3) 0.85553(19) 0.0438(11) Uani 1 2 d S TU P . .
C6 C 0.84361(18) 0.6872(4) 0.7999(2) 0.0524(13) Uani 1 2 d S TU P . .
C7 C 0.8231(3) 0.6462(5) 0.7500 0.0490(17) Uani 1 4 d S TU P . .
C8 C 0.8103(9) 0.5538(8) 0.7500 0.076(4) Uani 0.5 2 d S TU P . .
H8A H 0.7950 0.5277 0.7139 0.114 Uiso 0.25 1 d R U P . .
H8B H 0.8667 0.5690 0.7580 0.114 Uiso 0.25 1 d R U P . .
H8C H 0.7745 0.5159 0.7781 0.114 Uiso 0.25 1 d R U P . .
C9 C 0.8446(5) 0.7659(5) 0.8010(3) 0.0565(19) Uani 0.5 1 d . U P . .
H9A H 0.8408 0.7907 0.8353 0.068 Uiso 0.5 1 d R U P . .
C10 C 0.8522(8) 0.8073(7) 0.7500 0.063(3) Uani 0.5 2 d S TU P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.958(2) 13_767 ?
Cu1 O2 1.958(3) 9_767 ?
Cu1 O1 1.963(3) 21 ?
Cu1 O1 1.963(3) . ?
Cu1 O1W 2.119(4) . ?
Cu1 Cu1 2.6549(10) 13_767 ?
O1 C1 1.260(4) . ?
O1W H1WA 0.8256 . ?
O2 C1 1.264(4) . ?
O2 Cu1 1.958(2) 13_767 ?
N1 N1 1.46(3) 21_565 ?
N1 C10 1.483(16) . ?
N1 H1A 0.9001 . ?
N1 H1B 0.9001 . ?
C1 C2 1.499(5) . ?
C2 C4 1.388(5) . ?
C2 C3 1.391(4) . ?
C3 C2 1.391(4) 20_655 ?
C3 H3A 0.9500 . ?
C4 C5 1.391(4) . ?
C4 H4A 0.9500 . ?
C5 C4 1.390(4) 20_655 ?
C5 C6 1.512(7) . ?
C6 C7 1.363(6) . ?
C6 C9 1.457(9) 20_655 ?
C6 C9 1.457(9) . ?
C7 C6 1.363(7) 16_557 ?
C7 C8 1.615(14) 20_655 ?
C7 C8 1.615(14) . ?
C8 C8 1.25(3) 20_655 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9601 . ?
C9 C10 1.408(9) . ?
C9 C9 1.429(16) 20_655 ?
C9 H9A 0.9600 . ?
C10 C9 1.408(9) 16_557 ?
C10 C10 1.92(3) 20_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 88.90(16) 13_767 9_767 ?
O2 Cu1 O1 88.81(12) 13_767 21 ?
O2 Cu1 O1 168.09(11) 9_767 21 ?
O2 Cu1 O1 168.09(11) 13_767 . ?
O2 Cu1 O1 88.81(12) 9_767 . ?
O1 Cu1 O1 91.04(17) 21 . ?
O2 Cu1 O1W 97.50(14) 13_767 . ?
O2 Cu1 O1W 97.50(14) 9_767 . ?
O1 Cu1 O1W 94.39(15) 21 . ?
O1 Cu1 O1W 94.39(15) . . ?
O2 Cu1 Cu1 84.43(8) 13_767 13_767 ?
O2 Cu1 Cu1 84.43(8) 9_767 13_767 ?
O1 Cu1 Cu1 83.72(8) 21 13_767 ?
O1 Cu1 Cu1 83.72(8) . 13_767 ?
O1W Cu1 Cu1 177.28(18) . 13_767 ?
C1 O1 Cu1 123.2(2) . . ?
Cu1 O1W H1WA 108.7 . . ?
C1 O2 Cu1 122.5(2) . 13_767 ?
N1 N1 C10 177.8(8) 21_565 . ?
N1 N1 H1A 59.9 21_565 . ?
C10 N1 H1A 119.9 . . ?
N1 N1 H1B 60.1 21_565 . ?
C10 N1 H1B 120.1 . . ?
H1A N1 H1B 120.0 . . ?
O1 C1 O2 126.2(3) . . ?
O1 C1 C2 117.1(3) . . ?
O2 C1 C2 116.8(3) . . ?
C4 C2 C3 120.0(3) . . ?
C4 C2 C1 120.5(3) . . ?
C3 C2 C1 119.4(3) . . ?
C2 C3 C2 119.6(4) 20_655 . ?
C2 C3 H3A 120.2 20_655 . ?
C2 C3 H3A 120.2 . . ?
C2 C4 C5 120.6(3) . . ?
C2 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C4 119.0(4) 20_655 . ?
C4 C5 C6 120.5(2) 20_655 . ?
C4 C5 C6 120.5(2) . . ?
C7 C6 C9 116.0(5) . 20_655 ?
C7 C6 C9 116.0(5) . . ?
C9 C6 C9 58.7(7) 20_655 . ?
C7 C6 C5 122.2(6) . . ?
C9 C6 C5 113.8(5) 20_655 . ?
C9 C6 C5 113.8(5) . . ?
C6 C7 C6 121.9(8) . 16_557 ?
C6 C7 C8 116.6(4) . 20_655 ?
C6 C7 C8 116.6(4) 16_557 20_655 ?
C6 C7 C8 116.6(3) . . ?
C6 C7 C8 116.6(3) 16_557 . ?
C8 C7 C8 45.3(11) 20_655 . ?
C7 C8 C8 67.3(5) . 20_655 ?
C7 C8 H8A 112.8 . . ?
C8 C8 H8A 87.4 20_655 . ?
C7 C8 H8B 97.4 . . ?
C8 C8 H8B 161.1 20_655 . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 117.5 . . ?
C8 C8 H8C 70.9 20_655 . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C9 100.0(7) . 20_655 ?
C10 C9 C6 118.9(7) . . ?
C9 C9 C6 60.6(3) 20_655 . ?
C10 C9 H9A 119.1 . . ?
C9 C9 H9A 108.3 20_655 . ?
C6 C9 H9A 122.0 . . ?
C9 C10 C9 119.5(11) . 16_557 ?
C9 C10 N1 120.0(5) . . ?
C9 C10 N1 120.0(5) 16_557 . ?
C9 C10 C10 80.0(7) . 20_655 ?
C9 C10 C10 80.0(7) 16_557 20_655 ?
N1 C10 C10 117.8(8) . 20_655 ?

_refine_diff_density_max         1.131
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.068



