# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_Cu_CP_COOH
_database_code_depnum_ccdc_archive 'CCDC 2287966'
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 Cu N4 O9'
_chemical_formula_weight         605.99

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   5.1004(7)
_cell_length_b                   20.907(3)
_cell_length_c                   21.437(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.484(4)
_cell_angle_gamma                90.00
_cell_volume                     2279.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    38329
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      31.52

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1236
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37672
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_sigmaI/netI    0.0926
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         31.52
_reflns_number_total             7574
_reflns_number_gt                4064
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (1998)'

_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     
'calc w=1/[σ²(Fo²)+(0.1510P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7574
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2602
_refine_ls_wR_factor_gt          0.2069
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.18547(11) 0.00208(2) 0.23918(2) 0.02224(17) Uani 1 1 d . . .
N1 N 0.4290(7) 0.00403(15) 0.16722(17) 0.0195(7) Uani 1 1 d . . .
C1 C 0.6287(9) -0.0381(2) 0.1671(2) 0.0270(9) Uani 1 1 d . . .
H1A H 0.6504 -0.0678 0.1994 0.032 Uiso 1 1 calc R . .
O1 O 0.3331(6) -0.07896(15) 0.26838(15) 0.0294(7) Uani 1 1 d . . .
O2 O 0.0637(8) -0.14204(18) 0.20952(19) 0.0454(10) Uani 1 1 d . . .
N2 N 1.4868(8) 0.49262(15) -0.18047(19) 0.0252(8) Uani 1 1 d . . .
C2 C 0.8030(9) -0.0391(2) 0.1207(2) 0.0279(10) Uani 1 1 d . . .
H2A H 0.9362 -0.0695 0.1217 0.033 Uiso 1 1 calc R . .
O3 O 0.1476(7) -0.37759(17) 0.23467(16) 0.0355(8) Uani 1 1 d . . .
N3 N 0.5519(7) 0.10168(18) 0.03007(18) 0.0272(8) Uani 1 1 d . . .
H3B H 0.3952 0.1132 0.0171 0.033 Uiso 1 1 calc R . .
C3 C 0.7778(11) 0.0054(2) 0.0731(2) 0.0314(10) Uani 1 1 d . . .
H3A H 0.8884 0.0045 0.0407 0.038 Uiso 1 1 calc R . .
O4 O 0.4834(6) -0.41907(14) 0.29194(14) 0.0263(7) Uani 1 1 d . . .
N4 N 1.0264(8) 0.38496(18) -0.11071(18) 0.0304(9) Uani 1 1 d . . .
H4A H 0.9298 0.3746 -0.1439 0.036 Uiso 1 1 calc R . .
C4 C 0.5819(9) 0.0520(2) 0.0749(2) 0.0245(9) Uani 1 1 d . . .
O5 O 1.1150(7) -0.27579(17) 0.41208(18) 0.0393(9) Uani 1 1 d . . .
C5 C 0.4128(9) 0.0485(2) 0.1216(2) 0.0266(9) Uani 1 1 d . . .
H5A H 0.2788 0.0786 0.1217 0.032 Uiso 1 1 calc R . .
O6 O 1.0344(8) -0.17157(17) 0.41181(19) 0.0451(10) Uani 1 1 d . . .
H6A H 1.0484 -0.1704 0.4516 0.054 Uiso 1 1 d R . .
C6 C 0.7576(9) 0.1321(2) 0.0064(2) 0.0266(9) Uani 1 1 d . . .
C7 C 0.6932(9) 0.1889(2) -0.0332(2) 0.0239(9) Uani 1 1 d . . .
O7 O 0.9849(7) 0.11467(19) 0.0180(2) 0.0442(10) Uani 1 1 d . . .
C8 C 0.8629(9) 0.2414(2) -0.0276(2) 0.0253(9) Uani 1 1 d . . .
H8A H 1.0074 0.2408 0.0017 0.030 Uiso 1 1 calc R . .
O8 O 1.1196(8) 0.36244(17) -0.00768(16) 0.0392(9) Uani 1 1 d . . .
O9 O 0.2301(7) 0.24587(16) -0.16194(16) 0.0348(8) Uani 1 1 d . . .
H9A H 0.0878 0.2364 -0.1460 0.042 Uiso 1 1 d R . .
C9 C 0.8148(9) 0.2945(2) -0.0660(2) 0.0243(9) Uani 1 1 d . . .
C10 C 0.6001(9) 0.2945(2) -0.1101(2) 0.0253(9) Uani 1 1 d . . .
H10A H 0.5677 0.3301 -0.1355 0.030 Uiso 1 1 calc R . .
C11 C 0.4335(9) 0.2421(2) -0.1167(2) 0.0268(9) Uani 1 1 d . . .
C12 C 0.4743(9) 0.1898(2) -0.0769(2) 0.0270(9) Uani 1 1 d . . .
H12A H 0.3569 0.1557 -0.0794 0.032 Uiso 1 1 calc R . .
C13 C 0.9995(9) 0.3497(2) -0.0578(2) 0.0278(10) Uani 1 1 d . . .
C14 C 1.1987(10) 0.4365(2) -0.1150(2) 0.0293(10) Uani 1 1 d . . .
C15 C 1.2552(15) 0.4803(3) -0.0679(3) 0.0527(17) Uani 1 1 d . . .
H15A H 1.1787 0.4767 -0.0301 0.063 Uiso 1 1 calc R . .
C16 C 1.4255(16) 0.5290(3) -0.0777(3) 0.062(2) Uani 1 1 d . . .
H16A H 1.4600 0.5598 -0.0469 0.074 Uiso 1 1 calc R . .
C17 C 1.5457(13) 0.5329(3) -0.1323(3) 0.0433(14) Uani 1 1 d . . .
H17A H 1.6722 0.5643 -0.1364 0.052 Uiso 1 1 calc R . .
C18 C 1.3160(9) 0.4452(2) -0.1713(2) 0.0269(9) Uani 1 1 d . . .
H18A H 1.2738 0.4168 -0.2039 0.032 Uiso 1 1 calc R . .
C19 C 0.2485(10) -0.1342(2) 0.2494(2) 0.0270(9) Uani 1 1 d . . .
C20 C 0.3960(9) -0.19041(19) 0.2788(2) 0.0221(8) Uani 1 1 d . . .
C21 C 0.6157(9) -0.18292(19) 0.3216(2) 0.0262(9) Uani 1 1 d . . .
H21A H 0.6731 -0.1421 0.3331 0.031 Uiso 1 1 calc R . .
C22 C 0.7492(9) -0.2362(2) 0.3470(2) 0.0241(9) Uani 1 1 d . . .
C23 C 0.9820(9) -0.2305(2) 0.3936(2) 0.0276(9) Uani 1 1 d . . .
C24 C 0.6691(9) -0.2971(2) 0.3293(2) 0.0263(9) Uani 1 1 d . . .
H24A H 0.7638 -0.3325 0.3449 0.032 Uiso 1 1 calc R . .
C25 C 0.4470(9) -0.30573(19) 0.2882(2) 0.0225(8) Uani 1 1 d . . .
C26 C 0.3503(9) -0.3710(2) 0.2698(2) 0.0223(9) Uani 1 1 d . . .
C27 C 0.3107(9) -0.25244(19) 0.2635(2) 0.0238(9) Uani 1 1 d . . .
H27A H 0.1611 -0.2583 0.2364 0.029 Uiso 1 1 calc R . .


_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 1.938(3) . ?
Cu1 O4 1.953(3) 2 ?
Cu1 N1 2.055(4) . ?
Cu1 N2 2.068(4) 4_466 ?
N1 C5 1.347(5) . ?
N1 C1 1.348(5) . ?
C1 C2 1.384(7) . ?
O1 C19 1.288(6) . ?
O2 C19 1.233(6) . ?
N2 C18 1.344(5) . ?
N2 C17 1.347(6) . ?
N2 Cu1 2.069(4) 4_765 ?
C2 C3 1.379(6) . ?
O3 C26 1.238(5) . ?
N3 C6 1.359(6) . ?
N3 C4 1.416(5) . ?
C3 C4 1.398(7) . ?
O4 C26 1.282(5) . ?
O4 Cu1 1.953(3) 2_545 ?
N4 C13 1.369(6) . ?
N4 C14 1.398(5) . ?
C4 C5 1.372(6) . ?
O5 C23 1.213(6) . ?
O6 C23 1.313(5) . ?
C6 O7 1.223(6) . ?
C6 C7 1.481(6) . ?
C7 C8 1.396(6) . ?
C7 C12 1.401(6) . ?
C8 C9 1.394(6) . ?
O8 C13 1.224(6) . ?
O9 C11 1.366(5) . ?
C9 C10 1.390(6) . ?
C9 C13 1.491(6) . ?
C10 C11 1.388(6) . ?
C11 C12 1.390(6) . ?
C14 C15 1.377(7) . ?
C14 C18 1.400(7) . ?
C15 C16 1.366(8) . ?
C16 C17 1.366(8) . ?
C19 C20 1.507(6) . ?
C20 C27 1.399(6) . ?
C20 C21 1.400(6) . ?
C21 C22 1.394(6) . ?
C22 C24 1.382(6) . ?
C22 C23 1.495(6) . ?
C24 C25 1.391(6) . ?
C25 C27 1.396(6) . ?
C25 C26 1.494(6) . ?

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 176.45(14) . 2 ?
O1 Cu1 N1 91.00(13) . . ?
O4 Cu1 N1 90.18(13) 2 . ?
O1 Cu1 N2 88.92(13) . 4_466 ?
O4 Cu1 N2 90.43(13) 2 4_466 ?
N1 Cu1 N2 171.16(15) . 4_466 ?
C5 N1 C1 116.9(4) . . ?
C5 N1 Cu1 123.6(3) . . ?
C1 N1 Cu1 119.4(3) . . ?
N1 C1 C2 122.6(4) . . ?
C19 O1 Cu1 124.7(3) . . ?
C18 N2 C17 117.2(4) . . ?
C18 N2 Cu1 121.8(3) . 4_765 ?
C17 N2 Cu1 120.7(3) . 4_765 ?
C3 C2 C1 119.6(4) . . ?
C6 N3 C4 123.5(4) . . ?
C2 C3 C4 118.4(5) . . ?
C26 O4 Cu1 109.2(3) . 2_545 ?
C13 N4 C14 125.1(4) . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 N3 119.6(4) . . ?
C3 C4 N3 122.2(4) . . ?
N1 C5 C4 124.1(4) . . ?
O7 C6 N3 122.1(4) . . ?
O7 C6 C7 121.3(4) . . ?
N3 C6 C7 116.5(4) . . ?
C8 C7 C12 120.2(4) . . ?
C8 C7 C6 118.2(4) . . ?
C12 C7 C6 121.6(4) . . ?
C9 C8 C7 119.7(4) . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 C13 122.5(4) . . ?
C8 C9 C13 117.8(4) . . ?
C11 C10 C9 120.8(4) . . ?
O9 C11 C10 116.8(4) . . ?
O9 C11 C12 123.3(4) . . ?
C10 C11 C12 119.8(4) . . ?
C11 C12 C7 119.6(4) . . ?
O8 C13 N4 122.3(4) . . ?
O8 C13 C9 122.7(4) . . ?
N4 C13 C9 115.0(4) . . ?
C15 C14 N4 124.1(5) . . ?
C15 C14 C18 117.8(4) . . ?
N4 C14 C18 118.1(4) . . ?
C16 C15 C14 118.9(5) . . ?
C15 C16 C17 120.6(5) . . ?
N2 C17 C16 122.1(5) . . ?
N2 C18 C14 123.2(4) . . ?
O2 C19 O1 123.9(4) . . ?
O2 C19 C20 121.1(4) . . ?
O1 C19 C20 115.0(4) . . ?
C27 C20 C21 118.4(4) . . ?
C27 C20 C19 119.3(4) . . ?
C21 C20 C19 122.3(4) . . ?
C22 C21 C20 120.6(4) . . ?
C24 C22 C21 120.2(4) . . ?
C24 C22 C23 117.4(4) . . ?
C21 C22 C23 122.4(4) . . ?
O5 C23 O6 122.7(4) . . ?
O5 C23 C22 123.4(4) . . ?
O6 C23 C22 113.9(4) . . ?
C22 C24 C25 120.1(4) . . ?
C24 C25 C27 119.6(4) . . ?
C24 C25 C26 121.4(4) . . ?
C27 C25 C26 119.0(4) . . ?
O3 C26 O4 122.1(4) . . ?
O3 C26 C25 120.3(4) . . ?
O4 C26 C25 117.6(4) . . ?
C25 C27 C20 120.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        31.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.640
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.257
####################################################################### 
# 
# 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_Cu_CP-NO2
_database_code_depnum_ccdc_archive 'CCDC 2287967'
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H24 Cu2 N6 O17'
_chemical_formula_weight         915.67

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n m a'

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

_cell_length_a                   13.3687(6)
_cell_length_b                   19.6383(9)
_cell_length_c                   12.8093(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3362.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    54831
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.34

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  0.838
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            52068
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4302
_reflns_number_gt                2850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT+ (Bruker, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (1998)'

_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     
'calc w=1/[σ²(Fo²)+(0.0501P)²+2.7570P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4302
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.63575(3) 0.024511(17) 0.61855(3) 0.02865(12) Uani 1 1 d . . .
O1 O 0.64608(15) 0.11936(10) 0.56800(15) 0.0334(5) Uani 1 1 d . . .
O1W O 0.48953(15) 0.03541(9) 0.61582(14) 0.0323(4) Uani 1 1 d . . .
H1WA H 0.4439 0.0113 0.6434 0.039 Uiso 1 1 d R . .
H1WB H 0.4764 0.0657 0.5704 0.039 Uiso 1 1 d R . .
C1 C 0.8265(3) -0.04663(16) 0.5908(3) 0.0414(8) Uani 1 1 d . . .
H1A H 0.7855 -0.0826 0.5706 0.050 Uiso 1 1 calc R . .
N1 N 0.78523(18) 0.01397(12) 0.61252(18) 0.0330(5) Uani 1 1 d . . .
N2 N 1.00557(19) 0.11829(12) 0.66126(19) 0.0369(6) Uani 1 1 d . . .
H2B H 0.9752 0.1567 0.6548 0.044 Uiso 1 1 calc R . .
O2 O 0.63981(17) 0.06803(10) 0.41424(17) 0.0422(5) Uani 1 1 d . . .
C2 C 0.9280(2) -0.05689(16) 0.5978(3) 0.0426(8) Uani 1 1 d . . .
H2A H 0.9544 -0.0997 0.5836 0.051 Uiso 1 1 calc R . .
N3 N 0.6543(2) 0.2500 0.1401(3) 0.0305(8) Uani 1 2 d S . .
O3 O 0.61807(15) -0.06864(10) 0.67225(17) 0.0384(5) Uani 1 1 d . . .
C3 C 0.9905(3) -0.00495(17) 0.6252(2) 0.0401(7) Uani 1 1 d . . .
H3A H 1.0590 -0.0120 0.6314 0.048 Uiso 1 1 calc R . .
C4 C 0.9484(2) 0.05930(15) 0.6437(2) 0.0330(7) Uani 1 1 d . . .
O4 O 0.59056(17) -0.12383(11) 0.52175(16) 0.0443(6) Uani 1 1 d . . .
N4 N 0.6000(3) -0.2500 0.9530(3) 0.0318(8) Uani 1 2 d S . .
C5 C 0.8457(2) 0.06564(15) 0.6379(2) 0.0330(7) Uani 1 1 d . . .
H5A H 0.8172 0.1078 0.6522 0.040 Uiso 1 1 calc R . .
O5 O 0.6556(3) 0.19682(13) 0.09474(19) 0.0784(10) Uani 1 1 d . . .
O6 O 0.5993(2) -0.19514(12) 0.99811(17) 0.0510(6) Uani 1 1 d . . .
C6 C 1.1039(2) 0.12075(16) 0.6874(2) 0.0338(7) Uani 1 1 d . . .
O7 O 1.15179(16) 0.06969(11) 0.71158(16) 0.0426(5) Uani 1 1 d . . .
C7 C 1.1535(2) 0.18870(16) 0.6810(2) 0.0342(7) Uani 1 1 d . . .
O8 O 1.4083(2) 0.2500 0.6381(3) 0.0650(11) Uani 1 2 d S . .
H8B H 1.4161 0.2812 0.5987 0.078 Uiso 0.50 1 d PR . .
C8 C 1.2564(2) 0.18903(19) 0.6628(2) 0.0447(8) Uani 1 1 d . . .
H8A H 1.2909 0.1481 0.6565 0.054 Uiso 1 1 calc R . .
C9 C 1.3069(3) 0.2500 0.6543(3) 0.0488(13) Uani 1 2 d S . .
C10 C 1.1020(3) 0.2500 0.6907(3) 0.0327(9) Uani 1 2 d S . .
H10A H 1.0335 0.2500 0.7036 0.039 Uiso 1 2 calc SR . .
C11 C 0.6446(2) 0.11990(14) 0.4690(2) 0.0294(6) Uani 1 1 d . . .
C12 C 0.6493(2) 0.18824(13) 0.4155(2) 0.0255(6) Uani 1 1 d . . .
C13 C 0.6513(2) 0.18863(14) 0.3070(2) 0.0270(6) Uani 1 1 d . . .
H13A H 0.6517 0.1479 0.2699 0.032 Uiso 1 1 calc R . .
C14 C 0.6528(3) 0.2500 0.2549(3) 0.0245(8) Uani 1 2 d S . .
C15 C 0.5982(3) -0.2500 0.6251(3) 0.0277(8) Uani 1 2 d S . .
H15A H 0.5949 -0.2500 0.5526 0.033 Uiso 1 2 calc SR . .
C16 C 0.6485(3) 0.2500 0.4693(3) 0.0255(8) Uani 1 2 d S . .
H16A H 0.6474 0.2500 0.5419 0.031 Uiso 1 2 calc SR . .
C17 C 0.6021(2) -0.12156(15) 0.6181(2) 0.0325(6) Uani 1 1 d . . .
C18 C 0.6006(2) -0.18806(13) 0.6784(2) 0.0251(6) Uani 1 1 d . . .
C19 C 0.6027(2) -0.18809(13) 0.7865(2) 0.0254(6) Uani 1 1 d . . .
H19A H 0.6048 -0.1474 0.8236 0.030 Uiso 1 1 calc R . .
C20 C 0.6015(3) -0.2500 0.8380(3) 0.0240(8) Uani 1 2 d S . .


_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 O1W 1.967(2) . ?
Cu1 O3 1.969(2) . ?
Cu1 O1 1.9769(19) . ?
Cu1 N1 2.011(2) . ?
Cu1 O7 2.360(2) 6_557 ?
O1 C11 1.269(3) . ?
C1 N1 1.341(4) . ?
C1 C2 1.375(5) . ?
N1 C5 1.337(4) . ?
N2 C6 1.358(4) . ?
N2 C4 1.406(4) . ?
O2 C11 1.238(3) . ?
C2 C3 1.364(5) . ?
N3 O5 1.195(3) . ?
N3 O5 1.195(3) 8_565 ?
N3 C14 1.471(5) . ?
O3 C17 1.268(4) . ?
C3 C4 1.402(4) . ?
C4 C5 1.380(4) . ?
O4 C17 1.244(3) . ?
N4 O6 1.223(2) . ?
N4 O6 1.223(2) 8 ?
N4 C20 1.473(5) . ?
C6 O7 1.229(3) . ?
C6 C7 1.492(4) . ?
O7 Cu1 2.360(2) 6_657 ?
C7 C8 1.396(4) . ?
C7 C10 1.392(4) . ?
O8 C9 1.371(5) . ?
C8 C9 1.379(4) . ?
C9 C8 1.379(4) 8_565 ?
C10 C7 1.392(4) 8_565 ?
C11 C12 1.508(4) . ?
C12 C13 1.391(4) . ?
C12 C16 1.395(3) . ?
C13 C14 1.378(3) . ?
C14 C13 1.378(3) 8_565 ?
C15 C18 1.395(3) . ?
C15 C18 1.395(3) 8 ?
C16 C12 1.395(3) 8_565 ?
C17 C18 1.518(4) . ?
C18 C19 1.385(4) . ?
C19 C20 1.383(3) . ?
C20 C19 1.383(3) 8 ?

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
O1W Cu1 O3 89.32(8) . . ?
O1W Cu1 O1 87.77(8) . . ?
O3 Cu1 O1 176.78(8) . . ?
O1W Cu1 N1 176.76(9) . . ?
O3 Cu1 N1 92.13(9) . . ?
O1 Cu1 N1 90.86(9) . . ?
O1W Cu1 O7 93.77(7) . 6_557 ?
O3 Cu1 O7 92.18(8) . 6_557 ?
O1 Cu1 O7 86.64(8) . 6_557 ?
N1 Cu1 O7 89.07(9) . 6_557 ?
C11 O1 Cu1 109.53(18) . . ?
N1 C1 C2 121.5(3) . . ?
C5 N1 C1 118.4(3) . . ?
C5 N1 Cu1 120.88(19) . . ?
C1 N1 Cu1 120.5(2) . . ?
C6 N2 C4 126.5(3) . . ?
C3 C2 C1 120.8(3) . . ?
O5 N3 O5 121.8(4) . 8_565 ?
O5 N3 C14 119.08(18) . . ?
O5 N3 C14 119.08(18) 8_565 . ?
C17 O3 Cu1 126.20(18) . . ?
C2 C3 C4 118.1(3) . . ?
C5 C4 N2 118.4(3) . . ?
C5 C4 C3 118.1(3) . . ?
N2 C4 C3 123.4(3) . . ?
O6 N4 O6 123.6(3) . 8 ?
O6 N4 C20 118.22(17) . . ?
O6 N4 C20 118.22(17) 8 . ?
N1 C5 C4 123.1(3) . . ?
O7 C6 N2 122.5(3) . . ?
O7 C6 C7 120.8(3) . . ?
N2 C6 C7 116.6(3) . . ?
C6 O7 Cu1 119.48(18) . 6_657 ?
C8 C7 C10 119.9(3) . . ?
C8 C7 C6 116.8(3) . . ?
C10 C7 C6 123.3(3) . . ?
C9 C8 C7 120.0(3) . . ?
O8 C9 C8 119.8(2) . . ?
O8 C9 C8 119.7(2) . 8_565 ?
C8 C9 C8 120.5(4) . 8_565 ?
C7 C10 C7 119.7(4) . 8_565 ?
O2 C11 O1 124.1(3) . . ?
O2 C11 C12 118.5(2) . . ?
O1 C11 C12 117.4(2) . . ?
C13 C12 C16 119.3(3) . . ?
C13 C12 C11 117.4(2) . . ?
C16 C12 C11 123.3(2) . . ?
C14 C13 C12 119.3(3) . . ?
C13 C14 C13 122.0(3) 8_565 . ?
C13 C14 N3 118.98(17) 8_565 . ?
C13 C14 N3 118.98(17) . . ?
C18 C15 C18 121.3(3) . 8 ?
C12 C16 C12 120.8(3) 8_565 . ?
O4 C17 O3 126.4(3) . . ?
O4 C17 C18 118.2(3) . . ?
O3 C17 C18 115.4(2) . . ?
C19 C18 C15 119.3(3) . . ?
C19 C18 C17 120.6(2) . . ?
C15 C18 C17 120.1(2) . . ?
C18 C19 C20 118.5(3) . . ?
C19 C20 C19 123.0(3) . 8 ?
C19 C20 N4 118.50(17) . . ?
C19 C20 N4 118.50(17) 8 . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.074



