# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_S130_0m
_database_code_depnum_ccdc_archive 'CCDC 1580147'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            S130
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H38 Cu2 N6 O4'
_chemical_formula_sum            'C34 H38 Cu2 N6 O4'
_chemical_formula_weight         721.78

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.4708(6)
_cell_length_b                   14.4673(7)
_cell_length_c                   9.4198(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.641(2)
_cell_angle_gamma                90
_cell_volume                     1545.49(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9772
_cell_measurement_theta_min      2.2819
_cell_measurement_theta_max      27.5105

_exptl_crystal_description       nugget
_exptl_crystal_colour            dark
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.158
_exptl_absorpt_coefficient_mu    1.426
_shelx_estimated_absorpt_T_min   0.669
_shelx_estimated_absorpt_T_max   0.806
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_process_details   
; SADABS
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_reflns_number            31312
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.282
_diffrn_reflns_theta_max         27.525
_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             3554
_reflns_number_gt                3310
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  ?
_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)+(0.0242P)²+1.1132P] 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         3554
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0562
_refine_ls_wR_factor_gt          0.0550
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
Cu1 Cu 0.55159(2) 0.40119(2) 0.56048(2) 0.01049(6) Uani 1 1 d . . . . .
N1 N 0.52477(10) 0.36122(8) 0.35071(12) 0.0136(2) Uani 1 1 d . . . . .
H1 H 0.5335(15) 0.4152(13) 0.3114(18) 0.016(4) Uiso 1 1 d . . . . .
C2 C 0.62738(12) 0.30422(10) 0.32935(15) 0.0179(3) Uani 1 1 d . . . . .
H2A H 0.634964 0.302138 0.226087 0.021 Uiso 1 1 calc R U . . .
H2B H 0.616721 0.240252 0.362454 0.021 Uiso 1 1 calc R U . . .
C3 C 0.73746(12) 0.34613(10) 0.41412(14) 0.0152(3) Uani 1 1 d . . . . .
H3A H 0.804942 0.303356 0.415046 0.018 Uiso 1 1 calc R U . . .
H3B H 0.756890 0.404986 0.369427 0.018 Uiso 1 1 calc R U . . .
N4 N 0.71479(10) 0.36289(8) 0.56192(12) 0.0121(2) Uani 1 1 d . . . . .
C5 C 0.80437(12) 0.38118(9) 0.66123(15) 0.0120(2) Uani 1 1 d . . . . .
C6 C 0.78859(12) 0.40152(9) 0.80929(14) 0.0118(2) Uani 1 1 d . . . . .
C7 C 0.68332(12) 0.44311(9) 0.83862(14) 0.0121(2) Uani 1 1 d . . . . .
O7 O 0.58589(8) 0.45217(7) 0.74756(10) 0.01397(19) Uani 1 1 d . . . . .
C8 C 0.68114(12) 0.48366(10) 0.97754(15) 0.0153(3) Uani 1 1 d . . . . .
H8 H 0.612570 0.515902 0.995046 0.018 Uiso 1 1 calc R U . . .
C9 C 0.77417(13) 0.47714(10) 1.08407(15) 0.0165(3) Uani 1 1 d . . . . .
H9 H 0.771392 0.507547 1.172882 0.020 Uiso 1 1 calc R U . . .
C10 C 0.87606(12) 0.42532(9) 1.06471(14) 0.0147(3) Uani 1 1 d . . . . .
C11 C 0.96744(13) 0.41051(10) 1.18115(16) 0.0196(3) Uani 1 1 d . . . . .
H11 H 0.960982 0.436739 1.272101 0.023 Uiso 1 1 calc R U . . .
C12 C 1.06492(13) 0.35920(11) 1.16549(17) 0.0225(3) Uani 1 1 d . . . . .
H12 H 1.127150 0.352019 1.243484 0.027 Uiso 1 1 calc R U . . .
C13 C 1.07163(13) 0.31754(10) 1.03323(17) 0.0216(3) Uani 1 1 d . . . . .
H13 H 1.138220 0.280705 1.022090 0.026 Uiso 1 1 calc R U . . .
C14 C 0.98259(12) 0.32923(10) 0.91829(16) 0.0170(3) Uani 1 1 d . . . . .
H14 H 0.987740 0.298075 0.830672 0.020 Uiso 1 1 calc R U . . .
C15 C 0.88379(12) 0.38651(9) 0.92788(15) 0.0133(3) Uani 1 1 d . . . . .
C16 C 0.92472(12) 0.39110(10) 0.61699(16) 0.0168(3) Uani 1 1 d . . . . .
H16A H 0.980200 0.415076 0.697891 0.025 Uiso 1 1 calc R U . . .
H16B H 0.920286 0.434043 0.535895 0.025 Uiso 1 1 calc R U . . .
H16C H 0.951905 0.330622 0.588415 0.025 Uiso 1 1 calc R U . . .
C17 C 0.41084(13) 0.32148(10) 0.28153(15) 0.0176(3) Uani 1 1 d . . . . .
H17A H 0.416307 0.307744 0.179784 0.021 Uiso 1 1 calc R U . . .
H17B H 0.348055 0.368256 0.283124 0.021 Uiso 1 1 calc R U . . .
C18 C 0.37600(14) 0.23402(10) 0.35317(17) 0.0223(3) Uani 1 1 d . . . . .
H18A H 0.298190 0.213653 0.306230 0.033 Uiso 1 1 calc R U . . .
H18B H 0.373082 0.246355 0.454879 0.033 Uiso 1 1 calc R U . . .
H18C H 0.434193 0.185514 0.344740 0.033 Uiso 1 1 calc R U . . .
N1' N 0.38836(10) 0.43691(9) 0.55669(13) 0.0166(2) Uani 1 1 d . . . . .
C2' C 0.28797(13) 0.42018(10) 0.55435(15) 0.0160(3) Uani 1 1 d . . . . .
O3' O 0.18464(10) 0.40677(9) 0.55258(16) 0.0338(3) Uani 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 O7 1.8964(10) . ?
Cu1 N1' 1.9376(12) . ?
Cu1 N4 1.9504(11) . ?
Cu1 N1 2.0374(11) . ?
N1 C2 1.4755(17) . ?
N1 C17 1.4856(17) . ?
N1 H1 0.876(18) . ?
C2 C3 1.5155(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N4 1.4743(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N4 C5 1.3084(17) . ?
C5 C6 1.4630(18) . ?
C5 C16 1.5077(18) . ?
C6 C7 1.4131(18) . ?
C6 C15 1.4564(18) . ?
C7 O7 1.3091(16) . ?
C7 C8 1.4377(18) . ?
C8 C9 1.3538(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.423(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4150(19) . ?
C10 C15 1.4209(19) . ?
C11 C12 1.369(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.4177(19) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.516(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1' C2' 1.1737(19) . ?
C2' O3' 1.1987(19) . ?

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
O7 Cu1 N1' 88.76(5) . . ?
O7 Cu1 N4 92.24(4) . . ?
N1' Cu1 N4 178.78(5) . . ?
O7 Cu1 N1 172.62(5) . . ?
N1' Cu1 N1 93.05(5) . . ?
N4 Cu1 N1 86.05(5) . . ?
C2 N1 C17 113.03(11) . . ?
C2 N1 Cu1 106.47(8) . . ?
C17 N1 Cu1 122.00(9) . . ?
C2 N1 H1 107.2(11) . . ?
C17 N1 H1 108.0(11) . . ?
Cu1 N1 H1 98.4(11) . . ?
N1 C2 C3 108.86(11) . . ?
N1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N4 C3 C2 108.19(11) . . ?
N4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
N4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C5 N4 C3 118.52(11) . . ?
C5 N4 Cu1 126.67(9) . . ?
C3 N4 Cu1 110.21(8) . . ?
N4 C5 C6 121.73(12) . . ?
N4 C5 C16 118.35(12) . . ?
C6 C5 C16 119.60(12) . . ?
C7 C6 C15 118.55(12) . . ?
C7 C6 C5 120.25(12) . . ?
C15 C6 C5 121.02(12) . . ?
O7 C7 C6 125.80(12) . . ?
O7 C7 C8 115.19(12) . . ?
C6 C7 C8 118.94(12) . . ?
C7 O7 Cu1 127.40(8) . . ?
C9 C8 C7 121.78(13) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 120.85(13) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C15 120.23(13) . . ?
C11 C10 C9 120.49(13) . . ?
C15 C10 C9 119.26(12) . . ?
C12 C11 C10 121.38(14) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.06(14) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.84(14) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 121.68(14) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C10 116.63(12) . . ?
C14 C15 C6 123.56(13) . . ?
C10 C15 C6 119.67(12) . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 113.65(12) . . ?
N1 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
N1 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2' N1' Cu1 152.63(12) . . ?
N1' C2' O3' 177.40(16) . . ?

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
C17 N1 C2 C3 -175.22(11) . . . . ?
Cu1 N1 C2 C3 -38.66(13) . . . . ?
N1 C2 C3 N4 49.90(15) . . . . ?
C2 C3 N4 C5 166.36(12) . . . . ?
C2 C3 N4 Cu1 -36.06(13) . . . . ?
C3 N4 C5 C6 177.99(11) . . . . ?
Cu1 N4 C5 C6 24.50(18) . . . . ?
C3 N4 C5 C16 4.46(18) . . . . ?
Cu1 N4 C5 C16 -149.03(10) . . . . ?
N4 C5 C6 C7 -29.20(19) . . . . ?
C16 C5 C6 C7 144.26(13) . . . . ?
N4 C5 C6 C15 155.82(12) . . . . ?
C16 C5 C6 C15 -30.72(18) . . . . ?
C15 C6 C7 O7 -172.22(12) . . . . ?
C5 C6 C7 O7 12.7(2) . . . . ?
C15 C6 C7 C8 10.86(18) . . . . ?
C5 C6 C7 C8 -164.24(12) . . . . ?
C6 C7 O7 Cu1 7.63(19) . . . . ?
C8 C7 O7 Cu1 -175.35(9) . . . . ?
N1' Cu1 O7 C7 168.92(11) . . . . ?
N4 Cu1 O7 C7 -10.39(11) . . . . ?
O7 C7 C8 C9 177.85(13) . . . . ?
C6 C7 C8 C9 -4.9(2) . . . . ?
C7 C8 C9 C10 -3.4(2) . . . . ?
C8 C9 C10 C11 -173.16(13) . . . . ?
C8 C9 C10 C15 5.2(2) . . . . ?
C15 C10 C11 C12 0.2(2) . . . . ?
C9 C10 C11 C12 178.57(13) . . . . ?
C10 C11 C12 C13 -2.7(2) . . . . ?
C11 C12 C13 C14 1.4(2) . . . . ?
C12 C13 C14 C15 2.6(2) . . . . ?
C13 C14 C15 C10 -4.9(2) . . . . ?
C13 C14 C15 C6 179.40(13) . . . . ?
C11 C10 C15 C14 3.56(19) . . . . ?
C9 C10 C15 C14 -174.86(12) . . . . ?
C11 C10 C15 C6 179.40(12) . . . . ?
C9 C10 C15 C6 0.99(19) . . . . ?
C7 C6 C15 C14 166.54(12) . . . . ?
C5 C6 C15 C14 -18.40(19) . . . . ?
C7 C6 C15 C10 -9.00(18) . . . . ?
C5 C6 C15 C10 166.06(12) . . . . ?
C2 N1 C17 C18 69.62(15) . . . . ?
Cu1 N1 C17 C18 -59.35(15) . . . . ?

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
N1 H1 O7 0.876(18) 2.374(18) 3.0666(15) 136.1(15) 3_666
N1 H1 N1' 0.876(18) 2.567(18) 3.1658(17) 126.3(14) 3_666

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_s137
_database_code_depnum_ccdc_archive 'CCDC 1580148'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H38 Cu2 N6 O2 S2, 2(C3 H7 N O), 2(H2 O)'
_chemical_formula_sum            'C40 H56 Cu2 N8 O6 S2'
_chemical_formula_weight         936.12

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'
S S 0.1246 0.1234 '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           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                   15.5100(4)
_cell_length_b                   7.1497(3)
_cell_length_c                   19.7873(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.121(2)
_cell_angle_gamma                90
_cell_volume                     2153.05(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30738
_cell_measurement_theta_min      1.34
_cell_measurement_theta_max      27.23

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    1.140
_shelx_estimated_absorpt_T_min   0.628
_shelx_estimated_absorpt_T_max   0.741
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.6202
_exptl_absorpt_correction_T_max  0.7713
_exptl_absorpt_process_details   'STOE XSHAPE/XRED'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            23622
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.533
_diffrn_reflns_theta_max         26.822
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4551
_reflns_number_gt                3977
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  ?
_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)+(0.0487P)²+0.4225P] 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         4551
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.44231(2) 0.33764(3) 0.43258(2) 0.02156(7) Uani 1 1 d . . . . .
N1 N 0.34412(9) 0.34982(19) 0.48820(7) 0.0242(3) Uani 1 1 d . . . . .
H1 H 0.3529(12) 0.450(3) 0.5105(10) 0.027(5) Uiso 1 1 d . . . . .
C2 C 0.26176(10) 0.3730(2) 0.43741(8) 0.0257(3) Uani 1 1 d . . . . .
H2A H 0.215002 0.421503 0.460396 0.031 Uiso 1 1 calc R U . . .
H2B H 0.242425 0.250866 0.416211 0.031 Uiso 1 1 calc R U . . .
C3 C 0.27788(10) 0.5089(2) 0.38261(8) 0.0246(3) Uani 1 1 d . . . . .
H3A H 0.226252 0.512997 0.344403 0.030 Uiso 1 1 calc R U . . .
H3B H 0.288055 0.636208 0.402243 0.030 Uiso 1 1 calc R U . . .
N4 N 0.35587(8) 0.44396(17) 0.35716(6) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.36745(9) 0.4910(2) 0.29609(8) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.44562(10) 0.4303(2) 0.27071(8) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.52605(10) 0.4053(2) 0.31694(8) 0.0238(3) Uani 1 1 d . . . . .
O7 O 0.53578(7) 0.39631(16) 0.38417(5) 0.0246(2) Uani 1 1 d . . . . .
C8 C 0.60544(10) 0.3965(2) 0.28943(8) 0.0279(3) Uani 1 1 d . . . . .
H8 H 0.660457 0.392194 0.320372 0.033 Uiso 1 1 calc R U . . .
C9 C 0.60402(10) 0.3941(2) 0.22086(9) 0.0291(3) Uani 1 1 d . . . . .
H9 H 0.657863 0.391719 0.204720 0.035 Uiso 1 1 calc R U . . .
C10 C 0.52300(10) 0.3950(2) 0.17244(8) 0.0254(3) Uani 1 1 d . . . . .
C11 C 0.52133(11) 0.3760(2) 0.10078(8) 0.0290(3) Uani 1 1 d . . . . .
H11 H 0.575117 0.369309 0.084674 0.035 Uiso 1 1 calc R U . . .
C12 C 0.44359(11) 0.3673(2) 0.05459(8) 0.0293(3) Uani 1 1 d . . . . .
H12 H 0.443297 0.356309 0.006702 0.035 Uiso 1 1 calc R U . . .
C13 C 0.36437(11) 0.3746(2) 0.07851(8) 0.0267(3) Uani 1 1 d . . . . .
H13 H 0.310142 0.365598 0.046752 0.032 Uiso 1 1 calc R U . . .
C14 C 0.36450(10) 0.3948(2) 0.14783(8) 0.0245(3) Uani 1 1 d . . . . .
H14 H 0.309960 0.398159 0.162908 0.029 Uiso 1 1 calc R U . . .
C15 C 0.44344(10) 0.4107(2) 0.19725(8) 0.0231(3) Uani 1 1 d . . . . .
C16 C 0.33992(11) 0.1961(2) 0.53809(9) 0.0294(3) Uani 1 1 d . . . . .
H16A H 0.394943 0.196545 0.573093 0.035 Uiso 1 1 calc R U . . .
H16B H 0.336833 0.075297 0.513289 0.035 Uiso 1 1 calc R U . . .
C17 C 0.26255(11) 0.2084(3) 0.57470(9) 0.0341(4) Uani 1 1 d . . . . .
H17A H 0.267696 0.110322 0.609847 0.051 Uiso 1 1 calc R U . . .
H17B H 0.207677 0.191610 0.541212 0.051 Uiso 1 1 calc R U . . .
H17C H 0.262380 0.331227 0.596663 0.051 Uiso 1 1 calc R U . . .
C18 C 0.30454(10) 0.6279(2) 0.25407(8) 0.0247(3) Uani 1 1 d . . . . .
H18A H 0.328571 0.669543 0.214288 0.037 Uiso 1 1 calc R U . . .
H18B H 0.296553 0.736049 0.282640 0.037 Uiso 1 1 calc R U . . .
H18C H 0.247744 0.566646 0.238043 0.037 Uiso 1 1 calc R U . . .
O1L O 0.83802(10) 0.3235(2) 0.38369(9) 0.0612(5) Uani 1 1 d . . . . .
C1L C 0.86138(13) 0.3536(3) 0.32922(12) 0.0465(5) Uani 1 1 d . . . . .
H1L H 0.816778 0.353944 0.288885 0.056 Uiso 1 1 calc R U . . .
N2L N 0.94243(9) 0.3858(2) 0.32077(8) 0.0328(3) Uani 1 1 d . . . . .
C3L C 1.01576(12) 0.3841(3) 0.37904(10) 0.0404(4) Uani 1 1 d . . . . .
H3LA H 1.053424 0.492807 0.376350 0.061 Uiso 1 1 calc R U . . .
H3LB H 1.049921 0.269179 0.377987 0.061 Uiso 1 1 calc R U . . .
H3LC H 0.993315 0.389120 0.422036 0.061 Uiso 1 1 calc R U . . .
C4L C 0.96384(14) 0.4103(3) 0.25306(10) 0.0431(4) Uani 1 1 d . . . . .
H4LA H 0.997024 0.526611 0.252167 0.065 Uiso 1 1 calc R U . . .
H4LB H 0.909517 0.416350 0.218344 0.065 Uiso 1 1 calc R U . . .
H4LC H 0.999446 0.304415 0.242952 0.065 Uiso 1 1 calc R U . . .
H1W H 0.6572(17) 0.280(4) 0.4327(13) 0.056(7) Uiso 1 1 d . . . . .
O1W O 0.70312(9) 0.26830(19) 0.45722(6) 0.0323(3) Uani 1 1 d . . . . .
H2W H 0.7390(16) 0.285(3) 0.4316(12) 0.053(7) Uiso 1 1 d . . . . .
N1' N 0.52879(8) 0.25203(19) 0.51248(7) 0.0250(3) Uani 1 1 d . . . . .
C2' C 0.55841(9) 0.1529(2) 0.55759(8) 0.0235(3) Uani 1 1 d . . . . .
S3' S 0.60025(3) 0.01547(5) 0.62169(2) 0.02710(10) Uani 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 O7 1.9317(10) . ?
Cu1 N4 1.9572(13) . ?
Cu1 N1' 1.9635(13) . ?
Cu1 N1 2.0456(13) . ?
Cu1 S3' 2.7730(4) 3_656 ?
N1 C2 1.4744(19) . ?
N1 C16 1.487(2) . ?
N1 H1 0.84(2) . ?
C2 C3 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N4 1.4722(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N4 C5 1.2999(19) . ?
C5 C6 1.465(2) . ?
C5 C18 1.512(2) . ?
C6 C7 1.409(2) . ?
C6 C15 1.454(2) . ?
C7 O7 1.3113(18) . ?
C7 C8 1.441(2) . ?
C8 C9 1.353(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.426(2) . ?
C9 H9 0.9500 . ?
C10 C15 1.418(2) . ?
C10 C11 1.420(2) . ?
C11 C12 1.367(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.400(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(2) . ?
C14 H14 0.9500 . ?
C16 C17 1.519(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1L C1L 1.221(3) . ?
C1L N2L 1.320(2) . ?
C1L H1L 0.9500 . ?
N2L C4L 1.452(2) . ?
N2L C3L 1.455(2) . ?
C3L H3LA 0.9800 . ?
C3L H3LB 0.9800 . ?
C3L H3LC 0.9800 . ?
C4L H4LA 0.9800 . ?
C4L H4LB 0.9800 . ?
C4L H4LC 0.9800 . ?
O1W H1W 0.79(3) . ?
O1W H2W 0.83(2) . ?
N1' C2' 1.163(2) . ?
C2' S3' 1.6366(16) . ?

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
O7 Cu1 N4 90.39(5) . . ?
O7 Cu1 N1' 90.31(5) . . ?
N4 Cu1 N1' 174.96(5) . . ?
O7 Cu1 N1 164.89(5) . . ?
N4 Cu1 N1 85.53(5) . . ?
N1' Cu1 N1 92.52(5) . . ?
O7 Cu1 S3' 98.68(4) . 3_656 ?
N4 Cu1 S3' 88.93(4) . 3_656 ?
N1' Cu1 S3' 95.89(4) . 3_656 ?
N1 Cu1 S3' 95.79(4) . 3_656 ?
C2 N1 C16 113.11(12) . . ?
C2 N1 Cu1 105.97(9) . . ?
C16 N1 Cu1 117.27(10) . . ?
C2 N1 H1 107.1(13) . . ?
C16 N1 H1 107.7(13) . . ?
Cu1 N1 H1 104.9(12) . . ?
N1 C2 C3 108.64(12) . . ?
N1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
N1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.3 . . ?
N4 C3 C2 107.63(12) . . ?
N4 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
N4 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C5 N4 C3 120.41(13) . . ?
C5 N4 Cu1 127.75(10) . . ?
C3 N4 Cu1 110.42(10) . . ?
N4 C5 C6 120.92(13) . . ?
N4 C5 C18 119.23(13) . . ?
C6 C5 C18 119.48(13) . . ?
C7 C6 C15 118.93(13) . . ?
C7 C6 C5 120.19(13) . . ?
C15 C6 C5 120.67(13) . . ?
O7 C7 C6 125.40(13) . . ?
O7 C7 C8 116.21(13) . . ?
C6 C7 C8 118.34(14) . . ?
C7 O7 Cu1 124.28(10) . . ?
C9 C8 C7 121.99(15) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 121.04(14) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C15 C10 C11 120.27(14) . . ?
C15 C10 C9 118.74(14) . . ?
C11 C10 C9 120.98(14) . . ?
C12 C11 C10 121.07(15) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.39(15) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.47(15) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 122.03(14) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C10 116.66(14) . . ?
C14 C15 C6 123.24(13) . . ?
C10 C15 C6 119.99(14) . . ?
N1 C16 C17 114.43(14) . . ?
N1 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
N1 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1L C1L N2L 126.5(2) . . ?
O1L C1L H1L 116.8 . . ?
N2L C1L H1L 116.8 . . ?
C1L N2L C4L 122.06(18) . . ?
C1L N2L C3L 121.08(17) . . ?
C4L N2L C3L 116.70(15) . . ?
N2L C3L H3LA 109.5 . . ?
N2L C3L H3LB 109.5 . . ?
H3LA C3L H3LB 109.5 . . ?
N2L C3L H3LC 109.5 . . ?
H3LA C3L H3LC 109.5 . . ?
H3LB C3L H3LC 109.5 . . ?
N2L C4L H4LA 109.5 . . ?
N2L C4L H4LB 109.5 . . ?
H4LA C4L H4LB 109.5 . . ?
N2L C4L H4LC 109.5 . . ?
H4LA C4L H4LC 109.5 . . ?
H4LB C4L H4LC 109.5 . . ?
H1W O1W H2W 104(2) . . ?
C2' N1' Cu1 156.29(12) . . ?
N1' C2' S3' 179.33(14) . . ?
C2' S3' Cu1 102.55(5) . 3_656 ?

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
C16 N1 C2 C3 -170.62(13) . . . . ?
Cu1 N1 C2 C3 -40.81(14) . . . . ?
N1 C2 C3 N4 51.66(16) . . . . ?
C2 C3 N4 C5 156.07(13) . . . . ?
C2 C3 N4 Cu1 -36.47(14) . . . . ?
C3 N4 C5 C6 178.81(13) . . . . ?
Cu1 N4 C5 C6 13.7(2) . . . . ?
C3 N4 C5 C18 5.7(2) . . . . ?
Cu1 N4 C5 C18 -159.39(11) . . . . ?
N4 C5 C6 C7 -31.7(2) . . . . ?
C18 C5 C6 C7 141.40(15) . . . . ?
N4 C5 C6 C15 153.70(14) . . . . ?
C18 C5 C6 C15 -33.2(2) . . . . ?
C15 C6 C7 O7 -171.26(14) . . . . ?
C5 C6 C7 O7 14.0(2) . . . . ?
C15 C6 C7 C8 11.5(2) . . . . ?
C5 C6 C7 C8 -163.17(14) . . . . ?
C6 C7 O7 Cu1 20.2(2) . . . . ?
C8 C7 O7 Cu1 -162.53(11) . . . . ?
O7 C7 C8 C9 176.34(15) . . . . ?
C6 C7 C8 C9 -6.2(2) . . . . ?
C7 C8 C9 C10 -1.8(3) . . . . ?
C8 C9 C10 C15 4.0(2) . . . . ?
C8 C9 C10 C11 -174.46(16) . . . . ?
C15 C10 C11 C12 -1.8(2) . . . . ?
C9 C10 C11 C12 176.62(16) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C12 C13 C14 1.5(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C13 C14 C15 C10 -3.2(2) . . . . ?
C13 C14 C15 C6 -179.39(15) . . . . ?
C11 C10 C15 C14 3.8(2) . . . . ?
C9 C10 C15 C14 -174.74(15) . . . . ?
C11 C10 C15 C6 -179.92(14) . . . . ?
C9 C10 C15 C6 1.6(2) . . . . ?
C7 C6 C15 C14 166.64(15) . . . . ?
C5 C6 C15 C14 -18.7(2) . . . . ?
C7 C6 C15 C10 -9.4(2) . . . . ?
C5 C6 C15 C10 165.26(14) . . . . ?
C2 N1 C16 C17 -53.00(19) . . . . ?
Cu1 N1 C16 C17 -176.81(11) . . . . ?
O1L C1L N2L C4L 176.7(2) . . . . ?
O1L C1L N2L C3L 1.4(3) . . . . ?

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
N1 H1 O1W 0.84(2) 2.33(2) 3.0763(19) 148.3(16) 3_666
O1W H1W O7 0.79(3) 2.11(3) 2.8663(17) 161(3) .
O1W H2W O1L 0.83(2) 1.97(3) 2.7971(19) 171(2) .

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054

