# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1491826'
_audit_update_record             
;
2016-07-10 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H38 Cu2 N4 O17'
_chemical_formula_weight         733.62

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.2493(11)
_cell_length_b                   16.5313(17)
_cell_length_c                   8.4611(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1573.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    8107
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      30.05

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.429
_shelx_estimated_absorpt_T_min   0.716
_shelx_estimated_absorpt_T_max   0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7164
_exptl_absorpt_correction_T_max  0.7631
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8549
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.190
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             2749
_reflns_number_gt                2672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.955

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

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0357P)²+0.3989P] 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_abs_structure_details 
; 
 Flack x determined using 1102 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.029(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2749
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0645
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
Cu1 Cu 1.09547(3) 0.25085(2) 0.89173(4) 0.02837(13) Uani 1 1 d . . . . .
C1 C 1.0050(3) 0.2386(2) 0.5819(4) 0.0403(7) Uani 1 1 d . . . . .
C2 C 0.9794(4) 0.2093(3) 0.4312(4) 0.0607(11) Uani 1 1 d . . . . .
H2 H 0.9254 0.2364 0.3671 0.073 Uiso 1 1 calc R U . . .
C3 C 1.0339(4) 0.1407(3) 0.3782(5) 0.0718(13) Uani 1 1 d . . . . .
H3 H 1.0165 0.1202 0.2784 0.086 Uiso 1 1 calc R U . . .
C4 C 1.1157(4) 0.1017(3) 0.4751(5) 0.0632(11) Uani 1 1 d . . . . .
H4 H 1.1538 0.0550 0.4408 0.076 Uiso 1 1 calc R U . . .
C5 C 1.1398(4) 0.1337(2) 0.6245(4) 0.0502(9) Uani 1 1 d . . . . .
H5 H 1.1947 0.1081 0.6897 0.060 Uiso 1 1 calc R U . . .
C6 C 0.9489(3) 0.3134(2) 0.6500(4) 0.0414(8) Uani 1 1 d . . . . .
H6A H 0.9949 0.3607 0.6211 0.050 Uiso 1 1 calc R U . . .
H6B H 0.8689 0.3198 0.6090 0.050 Uiso 1 1 calc R U . . .
C7 C 0.9389(3) 0.37969(18) 0.9180(4) 0.0352(7) Uani 1 1 d . . . . .
H7 H 0.9991 0.4166 0.8755 0.042 Uiso 1 1 calc R U . . .
C8 C 0.9779(3) 0.3581(2) 1.0849(4) 0.0404(8) Uani 1 1 d . . . . .
C9 C 0.8212(3) 0.42444(18) 0.9115(5) 0.0419(8) Uani 1 1 d . . . . .
H9A H 0.8304 0.4758 0.9657 0.050 Uiso 1 1 calc R U . . .
H9B H 0.8030 0.4362 0.8018 0.050 Uiso 1 1 calc R U . . .
C10 C 0.7168(3) 0.38052(18) 0.9829(4) 0.0316(6) Uani 1 1 d . . . . .
N1 N 1.0846(2) 0.20086(16) 0.6751(3) 0.0356(6) Uani 1 1 d . . . . .
N2 N 0.9456(2) 0.30470(14) 0.8230(3) 0.0300(5) Uani 1 1 d . . . . .
H2A H 0.8904 0.2697 0.8583 0.045 Uiso 1 1 d R U . . .
O1 O 1.0546(2) 0.30060(14) 1.0957(3) 0.0400(5) Uani 1 1 d . . . . .
O2 O 0.9383(3) 0.39576(18) 1.1993(4) 0.0656(9) Uani 1 1 d . . . . .
O3 O 0.73056(18) 0.30660(13) 1.0185(3) 0.0350(5) Uani 1 1 d . . . . .
O4 O 0.6224(2) 0.41815(15) 1.0005(3) 0.0466(6) Uani 1 1 d . . . . .
O5 O 1.2137(2) 0.35462(16) 0.8174(3) 0.0512(6) Uani 1 1 d . . . . .
H5A H 1.2200 0.3740 0.7285 0.077 Uiso 1 1 d R U . . .
H5B H 1.2587 0.3680 0.8890 0.077 Uiso 1 1 d R U . . .
O6 O 0.8817(2) 0.08436(16) 0.9704(4) 0.0523(7) Uani 1 1 d . . . . .
H6C H 0.9466 0.1045 0.9903 0.078 Uiso 1 1 d R U . . .
H6D H 0.8684 0.0364 0.9874 0.078 Uiso 1 1 d R U . . .
O7 O 0.7648(2) 0.17113(17) 0.7297(3) 0.0583(7) Uani 1 1 d . . . . .
H7A H 0.7993 0.1399 0.7893 0.088 Uiso 1 1 d R U . . .
H7B H 0.6929 0.1788 0.7363 0.088 Uiso 1 1 d R U . . .
O8 O 0.2160(3) 0.4277(2) 0.5321(4) 0.0719(9) Uani 1 1 d . . . . .
H8A H 0.2302 0.4009 0.4526 0.108 Uiso 1 1 d R U . . .
H8B H 0.1558 0.4554 0.5389 0.108 Uiso 1 1 d R U . . .
O9 O 0.0000 0.5000 0.4306(4) 0.0609(11) Uani 1 2 d S T P . .
H9 H 0.0204 0.5340 0.3654 0.091 Uiso 1 1 d 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 O3 1.946(2) 4_557 ?
Cu1 O1 1.966(2) . ?
Cu1 N2 1.993(2) . ?
Cu1 N1 2.014(3) . ?
Cu1 O5 2.260(2) . ?
C1 N1 1.346(4) . ?
C1 C2 1.394(5) . ?
C1 C6 1.504(5) . ?
C2 C3 1.366(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.342(5) . ?
C5 H5 0.9300 . ?
C6 N2 1.471(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.480(4) . ?
C7 C9 1.518(4) . ?
C7 C8 1.522(5) . ?
C7 H7 0.9800 . ?
C8 O2 1.234(4) . ?
C8 O1 1.287(4) . ?
C9 C10 1.507(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O4 1.239(4) . ?
C10 O3 1.268(4) . ?
N2 H2A 0.8999 . ?
O3 Cu1 1.946(2) 4_457 ?
O5 H5A 0.8202 . ?
O5 H5B 0.8200 . ?
O6 H6C 0.8202 . ?
O6 H6D 0.8203 . ?
O7 H7A 0.8196 . ?
O7 H7B 0.8198 . ?
O8 H8A 0.8203 . ?
O8 H8B 0.8201 . ?
O9 H9 0.8201 . ?

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
O3 Cu1 O1 92.52(10) 4_557 . ?
O3 Cu1 N2 172.84(10) 4_557 . ?
O1 Cu1 N2 82.64(10) . . ?
O3 Cu1 N1 101.67(10) 4_557 . ?
O1 Cu1 N1 162.97(10) . . ?
N2 Cu1 N1 82.32(11) . . ?
O3 Cu1 O5 91.11(9) 4_557 . ?
O1 Cu1 O5 93.69(10) . . ?
N2 Cu1 O5 94.45(10) . . ?
N1 Cu1 O5 95.38(10) . . ?
N1 C1 C2 120.8(4) . . ?
N1 C1 C6 115.8(3) . . ?
C2 C1 C6 123.3(3) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 120.8(4) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
N2 C6 C1 108.2(3) . . ?
N2 C6 H6A 110.1 . . ?
C1 C6 H6A 110.1 . . ?
N2 C6 H6B 110.1 . . ?
C1 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
N2 C7 C9 115.7(3) . . ?
N2 C7 C8 107.0(2) . . ?
C9 C7 C8 113.6(3) . . ?
N2 C7 H7 106.7 . . ?
C9 C7 H7 106.7 . . ?
C8 C7 H7 106.7 . . ?
O2 C8 O1 124.0(4) . . ?
O2 C8 C7 120.4(3) . . ?
O1 C8 C7 115.6(3) . . ?
C10 C9 C7 115.5(3) . . ?
C10 C9 H9A 108.4 . . ?
C7 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C7 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
O4 C10 O3 124.1(3) . . ?
O4 C10 C9 118.3(3) . . ?
O3 C10 C9 117.6(3) . . ?
C5 N1 C1 120.2(3) . . ?
C5 N1 Cu1 127.0(2) . . ?
C1 N1 Cu1 112.6(2) . . ?
C6 N2 C7 117.4(3) . . ?
C6 N2 Cu1 108.2(2) . . ?
C7 N2 Cu1 105.02(18) . . ?
C6 N2 H2A 114.2 . . ?
C7 N2 H2A 108.8 . . ?
Cu1 N2 H2A 101.5 . . ?
C8 O1 Cu1 113.8(2) . . ?
C10 O3 Cu1 117.86(19) . 4_457 ?
Cu1 O5 H5A 127.0 . . ?
Cu1 O5 H5B 111.2 . . ?
H5A O5 H5B 121.3 . . ?
H6C O6 H6D 121.3 . . ?
H7A O7 H7B 121.5 . . ?
H8A O8 H8B 121.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.2(6) . . . . ?
C6 C1 C2 C3 -179.8(4) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C3 C4 C5 N1 0.4(7) . . . . ?
N1 C1 C6 N2 -29.1(4) . . . . ?
C2 C1 C6 N2 151.8(4) . . . . ?
N2 C7 C8 O2 -150.7(3) . . . . ?
C9 C7 C8 O2 -21.7(4) . . . . ?
N2 C7 C8 O1 30.6(4) . . . . ?
C9 C7 C8 O1 159.6(3) . . . . ?
N2 C7 C9 C10 65.9(4) . . . . ?
C8 C7 C9 C10 -58.5(4) . . . . ?
C7 C9 C10 O4 170.4(3) . . . . ?
C7 C9 C10 O3 -11.0(5) . . . . ?
C4 C5 N1 C1 -0.1(6) . . . . ?
C4 C5 N1 Cu1 174.1(3) . . . . ?
C2 C1 N1 C5 -0.7(5) . . . . ?
C6 C1 N1 C5 -179.8(3) . . . . ?
C2 C1 N1 Cu1 -175.7(3) . . . . ?
C6 C1 N1 Cu1 5.2(3) . . . . ?
C1 C6 N2 C7 156.9(3) . . . . ?
C1 C6 N2 Cu1 38.3(3) . . . . ?
C9 C7 N2 C6 70.9(4) . . . . ?
C8 C7 N2 C6 -161.4(3) . . . . ?
C9 C7 N2 Cu1 -168.8(2) . . . . ?
C8 C7 N2 Cu1 -41.1(3) . . . . ?
O2 C8 O1 Cu1 178.2(3) . . . . ?
C7 C8 O1 Cu1 -3.2(3) . . . . ?
O4 C10 O3 Cu1 -0.6(4) . . . 4_457 ?
C9 C10 O3 Cu1 -179.2(2) . . . 4_457 ?

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
O9 H9 O2 0.82 1.88 2.698(4) 174.0 2_664
O8 H8B O9 0.82 2.11 2.841(4) 148.3 .
O8 H8A O7 0.82 1.99 2.806(5) 175.8 4_456
O7 H7B O1 0.82 2.13 2.826(3) 142.0 4_457
O7 H7A O6 0.82 2.01 2.817(4) 167.0 .
O6 H6D O4 0.82 1.96 2.759(3) 164.6 3_647
O6 H6C O4 0.82 2.01 2.720(3) 143.8 4_557
O5 H5B O6 0.82 1.99 2.795(4) 168.2 4_557
O5 H5A O8 0.82 1.88 2.699(4) 171.9 1_655
N2 H2A O7 0.90 2.42 3.104(4) 133.5 .
N2 H2A O3 0.90 2.33 2.931(3) 123.8 .
C4 H4 O8 0.93 2.57 3.445(6) 156.1 3_646

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1491827'
_audit_update_record             
;
2016-07-10 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 Cu N2 O5, 2(H2 O)'
_chemical_formula_sum            'C13 H24 Cu N2 O7'
_chemical_formula_weight         383.88

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'
Cu Cu 0.3201 1.2651 '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                   7.2507(16)
_cell_length_b                   16.263(4)
_cell_length_c                   7.3756(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.652(4)
_cell_angle_gamma                90
_cell_volume                     868.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4387
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      30.18

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             402
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.293
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7640
_exptl_absorpt_correction_T_max  0.8101
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5000
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_point_group_measured_fraction_full 0.761
_reflns_number_total             2455
_reflns_number_gt                2404
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.467
_reflns_Friedel_fraction_max     0.502
_reflns_Friedel_fraction_full    0.506

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0584P)²+0.6370P] 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_abs_structure_details 
; 
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.038(8)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2455
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0762
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   0.844
_refine_ls_restrained_S_all      0.844
_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 0.43931(5) 1.11345(3) 0.45217(5) 0.02438(14) Uani 1 1 d . . . . .
N1 N 0.5908(4) 0.7247(2) 0.6682(5) 0.0264(7) Uani 1 1 d . . . . .
N2 N 0.4199(4) 1.0051(2) 0.5837(4) 0.0231(6) Uani 1 1 d . . . . .
H2 H 0.4464 1.0097 0.7041 0.035 Uiso 1 1 d R U . . .
O1 O 0.2008(4) 1.0818(2) 0.3382(4) 0.0364(7) Uani 1 1 d . . . . .
O2 O -0.0283(5) 0.9925(3) 0.3418(5) 0.0463(10) Uani 1 1 d . . . . .
O3 O 0.6351(5) 1.0716(2) 0.2412(4) 0.0469(9) Uani 1 1 d . . . . .
H3A H 0.7333 1.0489 0.2714 0.070 Uiso 1 1 d R U . . .
H3B H 0.6018 1.0784 0.1339 0.070 Uiso 1 1 d R U . . .
O4 O 0.6367(4) 1.1587(2) 0.6177(4) 0.0336(7) Uani 1 1 d . . . . .
O5 O 0.5830(5) 1.0964(2) 0.8775(4) 0.0427(9) Uani 1 1 d . . . . .
O6 O 0.1163(6) 0.3226(3) 0.6672(6) 0.0654(12) Uani 1 1 d . . . . .
H6C H 0.0692 0.2943 0.5848 0.098 Uiso 1 1 d R U . . .
H6D H 0.1081 0.3729 0.6650 0.098 Uiso 1 1 d R U . . .
O7 O 0.9305(6) 0.2245(3) 0.4003(7) 0.0681(13) Uani 1 1 d . . . . .
H7A H 0.9841 0.2082 0.3125 0.102 Uiso 1 1 d R U . . .
H7B H 0.8427 0.2564 0.3951 0.102 Uiso 1 1 d R U . . .
C1 C 0.5586(5) 0.7952(3) 0.5779(5) 0.0277(8) Uani 1 1 d . . . . .
H1 H 0.5101 0.7921 0.4583 0.033 Uiso 1 1 calc R U . . .
C2 C 0.5929(5) 0.8724(3) 0.6512(5) 0.0267(8) Uani 1 1 d . . . . .
C3 C 0.6656(6) 0.8760(3) 0.8304(6) 0.0338(9) Uani 1 1 d . . . . .
H3 H 0.6935 0.9265 0.8844 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6959(7) 0.8041(3) 0.9276(6) 0.0374(10) Uani 1 1 d . . . . .
H4 H 0.7397 0.8055 1.0488 0.045 Uiso 1 1 calc R U . . .
C5 C 0.6595(6) 0.7299(3) 0.8401(6) 0.0326(9) Uani 1 1 d . . . . .
H5 H 0.6841 0.6814 0.9042 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5687(5) 0.9483(3) 0.5335(5) 0.0290(9) Uani 1 1 d . . . . .
H6A H 0.6846 0.9782 0.5391 0.035 Uiso 1 1 calc R U . . .
H6B H 0.5428 0.9310 0.4086 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2303(5) 0.9714(3) 0.5543(6) 0.0295(9) Uani 1 1 d . . . . .
H7 H 0.2398 0.9135 0.5198 0.035 Uiso 1 1 calc R U . . .
C8 C 0.1272(5) 1.0176(3) 0.3971(6) 0.0309(9) Uani 1 1 d . . . . .
C9 C 0.1177(6) 0.9765(4) 0.7253(7) 0.0483(14) Uani 1 1 d . . . . .
H9 H -0.0061 0.9557 0.6893 0.058 Uiso 1 1 calc R U . . .
C10 C 0.1946(9) 0.9212(5) 0.8796(8) 0.070(2) Uani 1 1 d . . . . .
H10A H 0.1131 0.9224 0.9772 0.106 Uiso 1 1 calc R U . . .
H10B H 0.3146 0.9405 0.9225 0.106 Uiso 1 1 calc R U . . .
H10C H 0.2042 0.8658 0.8359 0.106 Uiso 1 1 calc R U . . .
C11 C 0.0928(9) 1.0636(5) 0.7893(8) 0.071(2) Uani 1 1 d . . . . .
H11A H 0.0450 1.0968 0.6894 0.106 Uiso 1 1 calc R U . . .
H11B H 0.2098 1.0852 0.8352 0.106 Uiso 1 1 calc R U . . .
H11C H 0.0078 1.0643 0.8838 0.106 Uiso 1 1 calc R U . . .
C12 C 0.6539(6) 1.1524(3) 0.7903(6) 0.0294(9) Uani 1 1 d . . . . .
C13 C 0.7643(8) 1.2187(4) 0.8884(7) 0.0510(13) Uani 1 1 d . . . . .
H13A H 0.8009 1.2006 1.0092 0.077 Uiso 1 1 calc R U . . .
H13B H 0.6902 1.2675 0.8945 0.077 Uiso 1 1 calc R U . . .
H13C H 0.8723 1.2306 0.8243 0.077 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 O1 1.943(3) . ?
Cu1 O4 1.964(3) . ?
Cu1 N2 2.021(3) . ?
Cu1 N1 2.021(3) 2_656 ?
Cu1 O3 2.277(3) . ?
N1 C5 1.335(5) . ?
N1 C1 1.340(6) . ?
N1 Cu1 2.021(3) 2_646 ?
N2 C7 1.483(5) . ?
N2 C6 1.485(5) . ?
N2 H2 0.9001 . ?
O1 C8 1.263(5) . ?
O2 C8 1.244(5) . ?
O3 H3A 0.8199 . ?
O3 H3B 0.8200 . ?
O4 C12 1.276(5) . ?
O5 C12 1.244(6) . ?
O6 H6C 0.8201 . ?
O6 H6D 0.8201 . ?
O7 H7A 0.8200 . ?
O7 H7B 0.8199 . ?
C1 C2 1.383(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(6) . ?
C2 C6 1.512(6) . ?
C3 C4 1.381(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.535(6) . ?
C7 C9 1.547(6) . ?
C7 H7 0.9800 . ?
C9 C11 1.508(10) . ?
C9 C10 1.528(8) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.502(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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 O4 164.00(14) . . ?
O1 Cu1 N2 83.67(12) . . ?
O4 Cu1 N2 95.64(13) . . ?
O1 Cu1 N1 88.77(13) . 2_656 ?
O4 Cu1 N1 89.55(14) . 2_656 ?
N2 Cu1 N1 169.33(13) . 2_656 ?
O1 Cu1 O3 101.62(14) . . ?
O4 Cu1 O3 94.32(14) . . ?
N2 Cu1 O3 97.62(13) . . ?
N1 Cu1 O3 91.27(13) 2_656 . ?
C5 N1 C1 117.5(4) . . ?
C5 N1 Cu1 119.8(3) . 2_646 ?
C1 N1 Cu1 122.5(3) . 2_646 ?
C7 N2 C6 114.5(3) . . ?
C7 N2 Cu1 110.1(2) . . ?
C6 N2 Cu1 110.4(2) . . ?
C7 N2 H2 108.2 . . ?
C6 N2 H2 100.7 . . ?
Cu1 N2 H2 112.6 . . ?
C8 O1 Cu1 117.0(3) . . ?
Cu1 O3 H3A 121.1 . . ?
Cu1 O3 H3B 117.4 . . ?
H3A O3 H3B 121.4 . . ?
C12 O4 Cu1 127.7(3) . . ?
H6C O6 H6D 121.3 . . ?
H7A O7 H7B 124.9 . . ?
N1 C1 C2 124.2(4) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 117.2(4) . . ?
C1 C2 C6 120.3(4) . . ?
C3 C2 C6 122.3(4) . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.4(4) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 123.0(4) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
N2 C6 C2 115.1(3) . . ?
N2 C6 H6A 108.5 . . ?
C2 C6 H6A 108.5 . . ?
N2 C6 H6B 108.5 . . ?
C2 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
N2 C7 C8 109.4(3) . . ?
N2 C7 C9 113.2(4) . . ?
C8 C7 C9 109.4(4) . . ?
N2 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
C9 C7 H7 108.2 . . ?
O2 C8 O1 123.6(4) . . ?
O2 C8 C7 118.4(4) . . ?
O1 C8 C7 117.9(3) . . ?
C11 C9 C10 111.4(6) . . ?
C11 C9 C7 112.6(5) . . ?
C10 C9 C7 112.9(5) . . ?
C11 C9 H9 106.4 . . ?
C10 C9 H9 106.4 . . ?
C7 C9 H9 106.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 O4 123.9(4) . . ?
O5 C12 C13 120.1(4) . . ?
O4 C12 C13 116.0(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.4(6) . . . . ?
Cu1 N1 C1 C2 -174.1(3) 2_646 . . . ?
N1 C1 C2 C3 0.0(6) . . . . ?
N1 C1 C2 C6 174.3(4) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C6 C2 C3 C4 -175.7(4) . . . . ?
C2 C3 C4 C5 2.6(7) . . . . ?
C1 N1 C5 C4 0.8(6) . . . . ?
Cu1 N1 C5 C4 175.4(4) 2_646 . . . ?
C3 C4 C5 N1 -2.3(7) . . . . ?
C7 N2 C6 C2 -67.1(4) . . . . ?
Cu1 N2 C6 C2 167.9(3) . . . . ?
C1 C2 C6 N2 115.2(4) . . . . ?
C3 C2 C6 N2 -70.8(5) . . . . ?
C6 N2 C7 C8 -110.8(4) . . . . ?
Cu1 N2 C7 C8 14.4(4) . . . . ?
C6 N2 C7 C9 126.9(4) . . . . ?
Cu1 N2 C7 C9 -107.9(4) . . . . ?
Cu1 O1 C8 O2 176.8(4) . . . . ?
Cu1 O1 C8 C7 1.0(5) . . . . ?
N2 C7 C8 O2 173.3(4) . . . . ?
C9 C7 C8 O2 -62.2(6) . . . . ?
N2 C7 C8 O1 -10.7(5) . . . . ?
C9 C7 C8 O1 113.9(5) . . . . ?
N2 C7 C9 C11 60.7(5) . . . . ?
C8 C7 C9 C11 -61.6(5) . . . . ?
N2 C7 C9 C10 -66.7(6) . . . . ?
C8 C7 C9 C10 171.0(5) . . . . ?
Cu1 O4 C12 O5 23.6(6) . . . . ?
Cu1 O4 C12 C13 -155.2(4) . . . . ?

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
N2 H2 O5 0.90 2.11 2.824(4) 135.8 .
O3 H3A O2 0.82 2.00 2.816(5) 179.1 1_655
O3 H3B O5 0.82 1.91 2.715(4) 167.0 1_554
O6 H6C O7 0.82 1.99 2.811(7) 173.8 1_455
O6 H6D O2 0.82 2.03 2.835(7) 167.6 2_546
O7 H7A O1 0.82 2.59 3.090(6) 121.0 1_645
C1 H1 O4 0.93 2.47 2.960(5) 113.3 2_646
C4 H4 O6 0.93 2.30 3.219(6) 170.9 2_657
C6 H6A O2 0.97 2.62 3.403(5) 137.4 1_655
C13 H13C O6 0.96 2.64 3.544(8) 157.0 1_665

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.070

_shelxl_version_number           2014/6

