# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_d:\syq\01\w
_audit_block_doi                 10.5517/cc141ff1
_database_code_depnum_ccdc_archive 'CCDC 1044062'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 Cu N2 O5'
_chemical_formula_weight         362.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.7922(6)
_cell_length_b                   14.9186(8)
_cell_length_c                   13.4193(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.130(5)
_cell_angle_gamma                90.00
_cell_volume                     1522.35(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    1.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7299
_exptl_absorpt_correction_T_max  0.8797
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12583
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3465
_reflns_number_gt                3237
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0404P)²+1.0091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3465
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.005
_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 -0.32886(3) -0.039100(17) 0.55281(2) 0.02261(10) Uani 1 1 d . . .
O1 O -0.2692(2) 0.07034(11) 0.50031(14) 0.0295(4) Uani 1 1 d . . .
O2 O -0.5466(2) 0.12296(11) 0.39980(14) 0.0308(4) Uani 1 1 d . . .
O3 O -0.6946(2) 0.32461(13) 0.06894(15) 0.0400(4) Uani 1 1 d . . .
O4 O -0.4985(2) 0.43109(11) 0.10605(13) 0.0294(4) Uani 1 1 d . . .
O5 O 0.0695(2) 0.28769(18) 0.3955(2) 0.0816(10) Uani 1 1 d . . .
H5 H 0.1330 0.2553 0.4503 0.098 Uiso 1 1 calc R . .
N1 N -0.1225(3) -0.04093(13) 0.70859(17) 0.0305(5) Uani 1 1 d . . .
N2 N 0.1395(3) -0.03237(16) 0.86010(19) 0.0417(6) Uani 1 1 d . . .
C1 C -0.3859(3) 0.12350(15) 0.43037(19) 0.0267(5) Uani 1 1 d . . .
C2 C -0.3290(3) 0.19332(16) 0.3764(2) 0.0299(5) Uani 1 1 d . . .
C3 C -0.1520(3) 0.20735(18) 0.4145(2) 0.0384(6) Uani 1 1 d . . .
H3 H -0.0670 0.1741 0.4759 0.046 Uiso 1 1 calc R . .
C4 C -0.1022(3) 0.27073(19) 0.3613(3) 0.0456(7) Uani 1 1 d . . .
C5 C -0.2286(3) 0.32101(18) 0.2696(2) 0.0398(6) Uani 1 1 d . . .
H5A H -0.1948 0.3643 0.2347 0.048 Uiso 1 1 calc R . .
C6 C -0.4061(3) 0.30583(16) 0.23064(19) 0.0291(5) Uani 1 1 d . . .
C7 C -0.5451(3) 0.35604(16) 0.12795(19) 0.0270(5) Uani 1 1 d . . .
C8 C -0.4564(3) 0.24280(16) 0.2841(2) 0.0288(5) Uani 1 1 d . . .
H8 H -0.5750 0.2335 0.2585 0.035 Uiso 1 1 calc R . .
C9 C 0.1137(4) 0.0225(3) 0.6771(3) 0.0552(9) Uani 1 1 d . . .
H9A H 0.0442 0.0031 0.5985 0.083 Uiso 1 1 calc R . .
H9B H 0.2330 0.0029 0.7076 0.083 Uiso 1 1 calc R . .
H9C H 0.1108 0.0868 0.6803 0.083 Uiso 1 1 calc R . .
C10 C 0.0419(3) -0.01616(17) 0.7460(2) 0.0306(5) Uani 1 1 d . . .
C11 C -0.1293(4) -0.0727(3) 0.8024(2) 0.0569(9) Uani 1 1 d . . .
H11 H -0.2295 -0.0939 0.8014 0.068 Uiso 1 1 calc R . .
C12 C 0.0321(4) -0.0682(3) 0.8959(3) 0.0669(11) Uani 1 1 d . . .
H12 H 0.0643 -0.0860 0.9704 0.080 Uiso 1 1 calc R . .
C13 C 0.3249(3) -0.0153(2) 0.9319(2) 0.0414(6) Uani 1 1 d . . .
C14 C 0.4372(5) -0.0845(3) 0.9722(4) 0.0993(19) Uani 1 1 d . . .
H14 H 0.3955 -0.1429 0.9531 0.119 Uiso 1 1 calc R . .
C15 C 0.3841(5) 0.0687(3) 0.9576(5) 0.0998(19) Uani 1 1 d . . .
H15 H 0.3059 0.1165 0.9285 0.120 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 O4 1.9488(15) 2_445 ?
Cu1 O1 1.9516(16) . ?
Cu1 N1 1.9633(19) . ?
Cu1 O2 1.9667(16) 3_456 ?
Cu1 Cu1 2.8538(5) 3_456 ?
O1 C1 1.263(3) . ?
O2 C1 1.258(3) . ?
O2 Cu1 1.9667(16) 3_456 ?
O3 C7 1.237(3) . ?
O4 C7 1.276(3) . ?
O4 Cu1 1.9488(15) 2_455 ?
O5 C4 1.363(3) . ?
N1 C10 1.323(3) . ?
N1 C11 1.375(3) . ?
N2 C10 1.350(3) . ?
N2 C12 1.366(4) . ?
N2 C13 1.439(3) . ?
C1 C2 1.492(3) . ?
C2 C3 1.388(3) . ?
C2 C8 1.393(3) . ?
C3 C4 1.382(4) . ?
C4 C5 1.392(3) . ?
C5 C6 1.393(3) . ?
C6 C8 1.383(3) . ?
C6 C7 1.504(3) . ?
C9 C10 1.474(4) . ?
C11 C12 1.343(4) . ?
C13 C15 1.334(5) . ?
C13 C14 1.340(5) . ?
C14 C15 1.388(5) 3_657 ?
C15 C14 1.388(5) 3_657 ?

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
O4 Cu1 O1 89.94(7) 2_445 . ?
O4 Cu1 N1 163.26(8) 2_445 . ?
O1 Cu1 N1 97.11(7) . . ?
O4 Cu1 O2 87.37(7) 2_445 3_456 ?
O1 Cu1 O2 160.60(7) . 3_456 ?
N1 Cu1 O2 90.79(8) . 3_456 ?
O4 Cu1 Cu1 60.12(5) 2_445 3_456 ?
O1 Cu1 Cu1 83.47(5) . 3_456 ?
N1 Cu1 Cu1 135.64(7) . 3_456 ?
O2 Cu1 Cu1 78.53(5) 3_456 3_456 ?
C1 O1 Cu1 121.88(15) . . ?
C1 O2 Cu1 127.97(14) . 3_456 ?
C7 O4 Cu1 106.75(14) . 2_455 ?
C10 N1 C11 106.9(2) . . ?
C10 N1 Cu1 130.52(17) . . ?
C11 N1 Cu1 122.59(18) . . ?
C10 N2 C12 108.1(2) . . ?
C10 N2 C13 126.1(2) . . ?
C12 N2 C13 125.8(2) . . ?
O2 C1 O1 126.8(2) . . ?
O2 C1 C2 116.22(19) . . ?
O1 C1 C2 117.0(2) . . ?
C3 C2 C8 120.0(2) . . ?
C3 C2 C1 120.9(2) . . ?
C8 C2 C1 119.1(2) . . ?
C4 C3 C2 120.0(2) . . ?
O5 C4 C3 122.5(2) . . ?
O5 C4 C5 117.1(2) . . ?
C3 C4 C5 120.4(2) . . ?
C4 C5 C6 119.4(2) . . ?
C8 C6 C5 120.4(2) . . ?
C8 C6 C7 119.3(2) . . ?
C5 C6 C7 120.3(2) . . ?
O3 C7 O4 123.1(2) . . ?
O3 C7 C6 120.7(2) . . ?
O4 C7 C6 116.1(2) . . ?
C6 C8 C2 119.8(2) . . ?
N1 C10 N2 109.4(2) . . ?
N1 C10 C9 127.0(2) . . ?
N2 C10 C9 123.6(2) . . ?
C12 C11 N1 109.1(3) . . ?
C11 C12 N2 106.5(3) . . ?
C15 C13 C14 120.4(3) . . ?
C15 C13 N2 120.2(3) . . ?
C14 C13 N2 119.4(3) . . ?
C13 C14 C15 119.8(4) . 3_657 ?
C13 C15 C14 119.8(3) . 3_657 ?

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
O5 H5 O3 0.82 1.96 2.771(3) 171.2 4_666

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_d:\syq\2-a\crysta~1\a
_audit_block_doi                 10.5517/cc141fg2
_database_code_depnum_ccdc_archive 'CCDC 1044063'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20.50 H17 Cu2 N2 O8.50'
_chemical_formula_weight         554.44

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'
Cu Cu 0.3201 1.2651 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   26.424(14)
_cell_length_b                   9.529(4)
_cell_length_c                   19.889(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.468(8)
_cell_angle_gamma                90.00
_cell_volume                     4129(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2240
_exptl_absorpt_coefficient_mu    2.116
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15677
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4732
_reflns_number_gt                4095
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0477P)²+1.3836P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4732
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.164603(14) 0.03849(3) 0.494913(18) 0.02774(10) Uani 1 1 d . . .
Cu2 Cu 0.275063(14) 0.15015(3) 0.465743(18) 0.02786(10) Uani 1 1 d . . .
O1 O 0.17330(9) -0.09744(19) 0.42471(11) 0.0351(4) Uani 1 1 d . . .
O2 O 0.20339(9) 0.05573(19) 0.36811(11) 0.0381(4) Uani 1 1 d . . .
O3 O 0.17479(9) -0.09774(19) 0.10074(12) 0.0392(4) Uani 1 1 d . . .
O4 O 0.19278(10) -0.32701(19) 0.10018(13) 0.0434(5) Uani 1 1 d . . .
O5 O 0.16765(10) -0.55531(18) 0.30367(11) 0.0403(5) Uani 1 1 d . . .
O6 O 0.10060(9) 0.1902(2) 0.39638(12) 0.0473(5) Uani 1 1 d . . .
O7 O 0.14427(9) 0.4020(2) 0.43933(12) 0.0438(5) Uani 1 1 d . . .
O8 O 0.0168(2) 0.7531(5) 0.2748(3) 0.0624(14) Uani 0.50 1 d P . .
O9 O 0.24161(8) 0.12797(17) 0.53040(10) 0.0247(3) Uani 1 1 d . . .
N1 N 0.09247(10) -0.0694(2) 0.47212(14) 0.0353(5) Uani 1 1 d . . .
N2 N 0.03773(10) -0.2419(2) 0.47312(16) 0.0398(5) Uani 1 1 d . . .
C1 C 0.18587(11) -0.0635(3) 0.37448(14) 0.0289(5) Uani 1 1 d . . .
C2 C 0.18083(11) -0.1756(3) 0.31748(14) 0.0273(5) Uani 1 1 d . . .
C3 C 0.18223(11) -0.1419(2) 0.25008(15) 0.0285(5) Uani 1 1 d . . .
H3 H 0.1856 -0.0488 0.2391 0.034 Uiso 1 1 calc R . .
C4 C 0.17866(11) -0.2479(3) 0.19947(15) 0.0286(5) Uani 1 1 d . . .
C5 C 0.17407(11) -0.3880(3) 0.21630(15) 0.0301(5) Uani 1 1 d . . .
H5 H 0.1725 -0.4592 0.1832 0.036 Uiso 1 1 calc R . .
C6 C 0.17190(12) -0.4202(2) 0.28269(15) 0.0293(5) Uani 1 1 d . . .
C7 C 0.17581(11) -0.3154(3) 0.33382(14) 0.0298(5) Uani 1 1 d . . .
H7 H 0.1751 -0.3381 0.3787 0.036 Uiso 1 1 calc R . .
C8 C 0.18237(11) -0.2204(3) 0.12743(15) 0.0296(5) Uani 1 1 d . . .
C9 C 0.14957(18) -0.6634(3) 0.24454(19) 0.0550(9) Uani 1 1 d . . .
H9A H 0.1118 -0.6376 0.1947 0.083 Uiso 1 1 calc R . .
H9B H 0.1439 -0.7496 0.2646 0.083 Uiso 1 1 calc R . .
H9C H 0.1809 -0.6759 0.2346 0.083 Uiso 1 1 calc R . .
C10 C 0.10152(12) 0.3195(3) 0.38890(17) 0.0371(6) Uani 1 1 d . . .
C11 C 0.04800(12) 0.3919(3) 0.31524(17) 0.0373(6) Uani 1 1 d . . .
C12 C 0.0000 0.3186(4) 0.2500 0.0323(8) Uani 1 2 d S . .
H12 H 0.0000 0.2210 0.2500 0.039 Uiso 1 2 calc SR . .
C13 C 0.04794(15) 0.5391(3) 0.3144(2) 0.0513(8) Uani 1 1 d . . .
H13 H 0.0806 0.5882 0.3577 0.062 Uiso 1 1 calc R . .
C14 C 0.0000 0.6109(5) 0.2500 0.0585(13) Uani 1 2 d S . .
C16 C 0.15366(13) -0.2754(3) 0.55419(19) 0.0496(8) Uani 1 1 d . . .
H16A H 0.1649 -0.3232 0.5220 0.074 Uiso 1 1 calc R . .
H16B H 0.1482 -0.3426 0.5856 0.074 Uiso 1 1 calc R . .
H16C H 0.1855 -0.2106 0.5903 0.074 Uiso 1 1 calc R . .
C17 C 0.09555(12) -0.1979(3) 0.49978(16) 0.0336(6) Uani 1 1 d . . .
C18 C 0.03159(15) -0.0302(3) 0.4263(2) 0.0583(10) Uani 1 1 d . . .
H18 H 0.0163 0.0548 0.3992 0.070 Uiso 1 1 calc R . .
C19 C -0.00226(15) -0.1352(3) 0.4272(3) 0.0628(10) Uani 1 1 d . . .
H19 H -0.0446 -0.1354 0.4016 0.075 Uiso 1 1 calc R . .
C20 C 0.01987(12) -0.3740(3) 0.48841(18) 0.0368(6) Uani 1 1 d . . .
C21 C 0.04575(13) -0.4972(3) 0.48619(19) 0.0426(7) Uani 1 1 d . . .
H21 H 0.0764 -0.4957 0.4766 0.051 Uiso 1 1 calc R . .
C22 C -0.02622(14) -0.3758(3) 0.5018(2) 0.0470(7) Uani 1 1 d . . .
H22 H -0.0440 -0.2922 0.5028 0.056 Uiso 1 1 calc R . .
C15 C 0.0302(4) 0.8427(8) 0.2768(5) 0.071(2) Uani 0.50 1 d P . .
H9 H 0.2712(13) 0.092(3) 0.5748(17) 0.030(7) Uiso 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 O9 1.9339(19) . ?
Cu1 N1 1.979(2) . ?
Cu1 O1 2.0109(18) . ?
Cu1 O3 2.045(2) 6_556 ?
Cu1 O6 2.245(2) . ?
Cu2 O4 1.9364(19) 4 ?
Cu2 O9 1.9407(18) . ?
Cu2 O7 1.949(2) 7_556 ?
Cu2 O2 2.0011(19) . ?
Cu2 O9 2.1699(19) 7_556 ?
Cu2 Cu2 3.0455(10) 7_556 ?
O1 C1 1.260(3) . ?
O2 C1 1.260(3) . ?
O3 C8 1.252(3) . ?
O3 Cu1 2.045(2) 6 ?
O4 C8 1.253(3) . ?
O4 Cu2 1.9364(19) 4_545 ?
O5 C6 1.377(3) . ?
O5 C9 1.427(3) . ?
O6 C10 1.243(4) . ?
O7 C10 1.272(3) . ?
O7 Cu2 1.949(2) 7_556 ?
O8 O8 0.878(8) 2 ?
O8 C15 0.917(8) . ?
O8 C15 1.372(7) 2 ?
O8 C14 1.424(6) . ?
O9 Cu2 2.1699(19) 7_556 ?
N1 C17 1.326(3) . ?
N1 C18 1.378(4) . ?
N2 C17 1.369(3) . ?
N2 C19 1.376(4) . ?
N2 C20 1.435(3) . ?
C1 C2 1.507(3) . ?
C2 C7 1.395(4) . ?
C2 C3 1.399(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.399(3) . ?
C4 C8 1.513(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.387(3) . ?
C10 C11 1.509(4) . ?
C11 C12 1.384(3) . ?
C11 C13 1.403(4) . ?
C12 C11 1.384(3) 2 ?
C13 C14 1.370(4) . ?
C14 C13 1.370(4) 2 ?
C14 O8 1.424(6) 2 ?
C16 C17 1.481(4) . ?
C18 C19 1.348(4) . ?
C20 C21 1.372(4) . ?
C20 C22 1.386(4) . ?
C21 C22 1.388(4) 5_546 ?
C22 C21 1.388(4) 5_546 ?
C15 C15 1.325(16) 2 ?
C15 O8 1.372(7) 2 ?

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
O9 Cu1 N1 172.13(9) . . ?
O9 Cu1 O1 91.56(7) . . ?
N1 Cu1 O1 88.87(8) . . ?
O9 Cu1 O3 90.25(7) . 6_556 ?
N1 Cu1 O3 85.86(8) . 6_556 ?
O1 Cu1 O3 153.19(8) . 6_556 ?
O9 Cu1 O6 98.74(8) . . ?
N1 Cu1 O6 88.99(9) . . ?
O1 Cu1 O6 97.72(9) . . ?
O3 Cu1 O6 108.43(9) 6_556 . ?
O4 Cu2 O9 179.14(8) 4 . ?
O4 Cu2 O7 91.50(10) 4 7_556 ?
O9 Cu2 O7 89.36(9) . 7_556 ?
O4 Cu2 O2 86.01(9) 4 . ?
O9 Cu2 O2 93.34(9) . . ?
O7 Cu2 O2 137.81(9) 7_556 . ?
O4 Cu2 O9 95.17(7) 4 7_556 ?
O9 Cu2 O9 84.55(7) . 7_556 ?
O7 Cu2 O9 110.28(8) 7_556 7_556 ?
O2 Cu2 O9 111.89(8) . 7_556 ?
O4 Cu2 Cu2 134.54(6) 4 7_556 ?
O9 Cu2 Cu2 45.18(5) . 7_556 ?
O7 Cu2 Cu2 103.88(7) 7_556 7_556 ?
O2 Cu2 Cu2 107.62(7) . 7_556 ?
O9 Cu2 Cu2 39.37(4) 7_556 7_556 ?
C1 O1 Cu1 124.78(16) . . ?
C1 O2 Cu2 120.50(17) . . ?
C8 O3 Cu1 126.18(16) . 6 ?
C8 O4 Cu2 132.22(17) . 4_545 ?
C6 O5 C9 118.1(2) . . ?
C10 O6 Cu1 133.37(19) . . ?
C10 O7 Cu2 127.1(2) . 7_556 ?
O8 O8 C15 99.7(7) 2 . ?
O8 O8 C15 41.2(4) 2 2 ?
C15 O8 C15 67.4(9) . 2 ?
O8 O8 C14 72.05(18) 2 . ?
C15 O8 C14 159.7(10) . . ?
C15 O8 C14 111.1(4) 2 . ?
Cu1 O9 Cu2 125.87(9) . . ?
Cu1 O9 Cu2 104.46(8) . 7_556 ?
Cu2 O9 Cu2 95.45(7) . 7_556 ?
C17 N1 C18 107.4(2) . . ?
C17 N1 Cu1 124.02(18) . . ?
C18 N1 Cu1 128.6(2) . . ?
C17 N2 C19 107.4(2) . . ?
C17 N2 C20 128.0(2) . . ?
C19 N2 C20 124.6(2) . . ?
O1 C1 O2 126.0(2) . . ?
O1 C1 C2 117.6(2) . . ?
O2 C1 C2 116.4(2) . . ?
C7 C2 C3 120.0(2) . . ?
C7 C2 C1 118.7(2) . . ?
C3 C2 C1 121.3(2) . . ?
C4 C3 C2 120.0(2) . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 C8 123.1(2) . . ?
C5 C4 C8 116.9(2) . . ?
C6 C5 C4 119.7(2) . . ?
O5 C6 C7 115.9(2) . . ?
O5 C6 C5 123.3(2) . . ?
C7 C6 C5 120.8(2) . . ?
C6 C7 C2 119.6(2) . . ?
O3 C8 O4 126.5(2) . . ?
O3 C8 C4 118.8(2) . . ?
O4 C8 C4 114.7(2) . . ?
O6 C10 O7 125.9(3) . . ?
O6 C10 C11 119.9(2) . . ?
O7 C10 C11 114.2(3) . . ?
C12 C11 C13 119.9(3) . . ?
C12 C11 C10 122.5(3) . . ?
C13 C11 C10 117.6(3) . . ?
C11 C12 C11 119.5(4) 2 . ?
C14 C13 C11 120.3(3) . . ?
C13 C14 C13 120.1(4) 2 . ?
C13 C14 O8 102.1(2) 2 2 ?
C13 C14 O8 137.8(3) . 2 ?
C13 C14 O8 137.8(3) 2 . ?
C13 C14 O8 102.1(2) . . ?
O8 C14 O8 35.9(3) 2 . ?
N1 C17 N2 109.2(2) . . ?
N1 C17 C16 124.0(2) . . ?
N2 C17 C16 126.7(2) . . ?
C19 C18 N1 109.0(3) . . ?
C18 C19 N2 106.9(3) . . ?
C21 C20 C22 120.2(3) . . ?
C21 C20 N2 120.9(2) . . ?
C22 C20 N2 118.8(3) . . ?
C20 C21 C22 120.0(3) . 5_546 ?
C20 C22 C21 119.8(3) . 5_546 ?
O8 C15 C15 72.9(6) . 2 ?
O8 C15 O8 39.1(5) . 2 ?
C15 C15 O8 39.7(3) 2 2 ?

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 O5 0.85(3) 2.04(3) 2.857(3) 161(3) 7_546

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_d:\syq\02b-un~1\w
_audit_block_doi                 10.5517/cc141fh3
_database_code_depnum_ccdc_archive 'CCDC 1044064'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 Cu N6 O9'
_chemical_formula_weight         669.12

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'
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   Pbcn

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

_cell_length_a                   13.5914(6)
_cell_length_b                   12.6315(7)
_cell_length_c                   18.4809(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3172.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       sheet
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8233
_exptl_absorpt_correction_T_max  0.9425
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25129
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3614
_reflns_number_gt                3403
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0742P)²+2.3153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3614
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.5000 0.03045(17) Uani 1 2 d S . .
O1 O 0.48535(14) 0.52156(17) 0.38872(13) 0.0503(5) Uani 1 1 d . . .
O2 O 0.52974(17) 0.66847(19) 0.44261(10) 0.0600(6) Uani 1 1 d . . .
O3 O 0.5000 0.9478(3) 0.2500 0.0788(12) Uani 1 2 d S . .
N1 N 0.36121(14) 0.54178(16) 0.51581(11) 0.0337(4) Uani 1 1 d . . .
N2 N 0.20020(13) 0.54774(16) 0.51823(11) 0.0335(4) Uani 1 1 d . . .
N3 N 0.2401(2) 0.5932(3) 0.25437(13) 0.0602(7) Uani 1 1 d . . .
C1 C 0.50711(17) 0.6195(2) 0.38732(15) 0.0437(6) Uani 1 1 d . . .
C2 C 0.50360(15) 0.6749(2) 0.31531(14) 0.0346(5) Uani 1 1 d . . .
C3 C 0.5000 0.6195(3) 0.2500 0.0356(7) Uani 1 2 d S . .
H3 H 0.5000 0.5459 0.2500 0.043 Uiso 1 2 calc SR . .
C4 C 0.50390(17) 0.7845(2) 0.31493(14) 0.0400(6) Uani 1 1 d . . .
H4 H 0.5067 0.8216 0.3584 0.048 Uiso 1 1 calc R . .
C5 C 0.5000 0.8390(3) 0.2500 0.0412(8) Uani 1 2 d S . .
C6 C 0.5030(5) 1.0099(5) 0.3030(5) 0.062(2) Uani 0.50 1 d P . .
C7 C 0.27660(18) 0.3924(2) 0.45332(15) 0.0444(6) Uani 1 1 d . . .
H7A H 0.3346 0.3870 0.4239 0.067 Uiso 1 1 calc R . .
H7B H 0.2194 0.3928 0.4229 0.067 Uiso 1 1 calc R . .
H7C H 0.2735 0.3331 0.4857 0.067 Uiso 1 1 calc R . .
C8 C 0.2802(2) 0.49177(18) 0.49573(11) 0.0312(5) Uani 1 1 d . . .
C9 C 0.33286(17) 0.63124(19) 0.55273(14) 0.0409(6) Uani 1 1 d . . .
H9 H 0.3754 0.6804 0.5733 0.049 Uiso 1 1 calc R . .
C10 C 0.23367(17) 0.63668(19) 0.55453(14) 0.0403(5) Uani 1 1 d . . .
H10 H 0.1956 0.6894 0.5758 0.048 Uiso 1 1 calc R . .
C11 C 0.09847(18) 0.5223(2) 0.50812(12) 0.0324(5) Uani 1 1 d . . .
C12 C 0.03612(18) 0.59972(19) 0.48230(15) 0.0385(5) Uani 1 1 d . . .
H12 H 0.0603 0.6664 0.4705 0.046 Uiso 1 1 calc R . .
C13 C 0.06363(17) 0.42302(19) 0.52597(15) 0.0380(5) Uani 1 1 d . . .
H13 H 0.1065 0.3716 0.5434 0.046 Uiso 1 1 calc R . .
C14 C 0.2719(5) 0.4866(4) 0.2461(2) 0.0895(16) Uani 1 1 d . . .
H14A H 0.3184 0.4698 0.2834 0.134 Uiso 1 1 calc R . .
H14B H 0.3023 0.4781 0.1996 0.134 Uiso 1 1 calc R . .
H14C H 0.2162 0.4401 0.2497 0.134 Uiso 1 1 calc R . .
C15 C 0.2344(5) 0.6338(5) 0.3241(3) 0.1076(17) Uani 1 1 d . . .
C16 C 0.2180(5) 0.6600(6) 0.1972(3) 0.128(2) Uani 1 1 d . . .
O4A O 0.2393(4) 0.6458(5) 0.1392(3) 0.1019(17) Uani 0.60 1 d P . .
O4B O 0.2136(7) 0.7180(9) 0.3295(6) 0.133(4) Uani 0.40 1 d P . .
O1W O 0.4787(2) 0.3121(3) 0.3264(2) 0.1005(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 N1 1.9805(19) . ?
Cu1 N1 1.9805(19) 5_666 ?
Cu1 O1 2.084(2) 5_666 ?
Cu1 O1 2.084(2) . ?
Cu1 O2 2.412(2) . ?
Cu1 O2 2.412(2) 5_666 ?
O1 C1 1.272(4) . ?
O2 C1 1.234(4) . ?
O3 C6 1.255(7) . ?
O3 C6 1.255(7) 4_655 ?
O3 C5 1.374(5) . ?
N1 C8 1.323(3) . ?
N1 C9 1.375(3) . ?
N2 C8 1.362(3) . ?
N2 C10 1.385(3) . ?
N2 C11 1.432(3) . ?
N3 C16 1.384(6) . ?
N3 C15 1.389(6) . ?
N3 C14 1.422(5) . ?
C1 C2 1.505(4) . ?
C2 C4 1.384(4) . ?
C2 C3 1.396(3) . ?
C3 C2 1.396(3) 4_655 ?
C4 C5 1.385(3) . ?
C5 C4 1.385(3) 4_655 ?
C6 C6 1.960(18) 4_655 ?
C7 C8 1.480(3) . ?
C9 C10 1.350(3) . ?
C11 C12 1.379(3) . ?
C11 C13 1.381(3) . ?
C12 C13 1.394(3) 5_566 ?
C13 C12 1.394(3) 5_566 ?
C15 O4B 1.106(10) . ?
C16 O4A 1.125(7) . ?

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
N1 Cu1 N1 180.0 . 5_666 ?
N1 Cu1 O1 88.87(8) . 5_666 ?
N1 Cu1 O1 91.13(8) 5_666 5_666 ?
N1 Cu1 O1 91.13(8) . . ?
N1 Cu1 O1 88.87(8) 5_666 . ?
O1 Cu1 O1 180.00(15) 5_666 . ?
N1 Cu1 O2 89.39(8) . . ?
N1 Cu1 O2 90.61(8) 5_666 . ?
O1 Cu1 O2 122.23(8) 5_666 . ?
O1 Cu1 O2 57.78(8) . . ?
N1 Cu1 O2 90.61(8) . 5_666 ?
N1 Cu1 O2 89.39(8) 5_666 5_666 ?
O1 Cu1 O2 57.78(8) 5_666 5_666 ?
O1 Cu1 O2 122.22(8) . 5_666 ?
O2 Cu1 O2 180.0 . 5_666 ?
C1 O1 Cu1 97.18(19) . . ?
C1 O2 Cu1 83.10(18) . . ?
C6 O3 C6 102.7(7) . 4_655 ?
C6 O3 C5 128.7(4) . . ?
C6 O3 C5 128.7(4) 4_655 . ?
C8 N1 C9 107.4(2) . . ?
C8 N1 Cu1 128.64(17) . . ?
C9 N1 Cu1 123.99(16) . . ?
C8 N2 C10 107.86(19) . . ?
C8 N2 C11 127.9(2) . . ?
C10 N2 C11 124.2(2) . . ?
C16 N3 C15 118.1(5) . . ?
C16 N3 C14 124.1(4) . . ?
C15 N3 C14 117.7(4) . . ?
O2 C1 O1 121.9(3) . . ?
O2 C1 C2 120.5(3) . . ?
O1 C1 C2 117.6(3) . . ?
C4 C2 C3 119.8(3) . . ?
C4 C2 C1 118.0(2) . . ?
C3 C2 C1 122.2(3) . . ?
C2 C3 C2 119.8(3) 4_655 . ?
C2 C4 C5 120.1(3) . . ?
O3 C5 C4 119.82(17) . 4_655 ?
O3 C5 C4 119.82(17) . . ?
C4 C5 C4 120.4(3) 4_655 . ?
O3 C6 C6 38.7(4) . 4_655 ?
N1 C8 N2 109.3(2) . . ?
N1 C8 C7 125.5(2) . . ?
N2 C8 C7 125.1(2) . . ?
C10 C9 N1 109.5(2) . . ?
C9 C10 N2 105.9(2) . . ?
C12 C11 C13 121.1(2) . . ?
C12 C11 N2 118.7(2) . . ?
C13 C11 N2 120.2(2) . . ?
C11 C12 C13 119.3(2) . 5_566 ?
C11 C13 C12 119.6(2) . 5_566 ?
O4B C15 N3 116.9(8) . . ?
O4A C16 N3 125.0(7) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_d:\syq\03b-sq~1\final
_audit_block_doi                 10.5517/cc141fj4
_database_code_depnum_ccdc_archive 'CCDC 1044065'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-05-19 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 H34 Cu2 N4 O12'
_chemical_formula_weight         817.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   23.182(11)
_cell_length_b                   12.610(5)
_cell_length_c                   17.333(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.001(7)
_cell_angle_gamma                90.00
_cell_volume                     3881(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    1.158
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8186
_exptl_absorpt_correction_T_max  0.8735
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14575
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4308
_reflns_number_gt                3826
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0443P)²+2.5155P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4308
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.292514(11) 0.148243(16) 0.152315(15) 0.02861(8) Uani 1 1 d . . .
O1 O 0.15349(7) 0.21688(10) 0.01197(10) 0.0373(3) Uani 1 1 d . . .
O2 O 0.20132(6) 0.05696(9) 0.07160(9) 0.0307(3) Uani 1 1 d . . .
O3 O -0.12119(7) 0.25515(10) -0.27297(10) 0.0384(3) Uani 1 1 d . . .
O4 O -0.18695(8) 0.10879(12) -0.35792(10) 0.0499(4) Uani 1 1 d . . .
O5 O -0.03541(7) -0.17566(11) -0.10244(11) 0.0459(4) Uani 1 1 d . . .
O1W O 0.30258(7) 0.13417(9) 0.04890(9) 0.0309(3) Uani 1 1 d . . .
H6A H 0.3251 0.1808 0.0413 0.037 Uiso 1 1 d R . .
H6B H 0.2609 0.1290 -0.0107 0.037 Uiso 1 1 d R . .
N1 N 0.29626(8) 0.13685(11) 0.26994(11) 0.0311(3) Uani 1 1 d . . .
N2 N 0.28197(9) 0.16180(11) 0.38214(12) 0.0305(3) Uani 1 1 d . . .
C2 C 0.14577(9) 0.11872(14) 0.01229(12) 0.0273(3) Uani 1 1 d . . .
C3 C 0.06824(9) 0.07121(13) -0.05906(12) 0.0274(3) Uani 1 1 d . . .
C4 C 0.00920(9) 0.13190(13) -0.13777(13) 0.0286(4) Uani 1 1 d . . .
H4 H 0.0177 0.2012 -0.1465 0.034 Uiso 1 1 calc R . .
C5 C -0.06302(9) 0.08882(14) -0.20389(12) 0.0290(4) Uani 1 1 d . . .
C6 C -0.07561(10) -0.01518(15) -0.19112(13) 0.0342(4) Uani 1 1 d . . .
H6 H -0.1235 -0.0445 -0.2365 0.041 Uiso 1 1 calc R . .
C7 C -0.01659(10) -0.07556(14) -0.11039(13) 0.0331(4) Uani 1 1 d . . .
C8 C 0.05531(9) -0.03233(13) -0.04466(13) 0.0311(4) Uani 1 1 d . . .
H8 H 0.0949 -0.0724 0.0090 0.037 Uiso 1 1 calc R . .
C9 C -0.12935(10) 0.15484(14) -0.28612(13) 0.0317(4) Uani 1 1 d . . .
C10 C 0.02182(10) -0.23795(14) -0.01685(15) 0.0384(4) Uani 1 1 d . . .
H10A H 0.0449 -0.1984 0.0448 0.046 Uiso 1 1 calc R . .
H10B H 0.0606 -0.2568 -0.0205 0.046 Uiso 1 1 calc R . .
C11 C -0.01590(13) -0.33651(16) -0.0185(2) 0.0539(6) Uani 1 1 d . . .
H11A H -0.0584 -0.3167 -0.0240 0.081 Uiso 1 1 calc R . .
H11B H 0.0193 -0.3758 0.0427 0.081 Uiso 1 1 calc R . .
H11C H -0.0325 -0.3797 -0.0751 0.081 Uiso 1 1 calc R . .
C12 C 0.22990(14) 0.30367(18) 0.24936(17) 0.0520(6) Uani 1 1 d . . .
H12A H 0.2650 0.3614 0.2829 0.078 Uiso 1 1 calc R . .
H12B H 0.1904 0.3137 0.2524 0.078 Uiso 1 1 calc R . .
H12C H 0.2088 0.3014 0.1802 0.078 Uiso 1 1 calc R . .
C13 C 0.26952(10) 0.20230(14) 0.29967(13) 0.0307(4) Uani 1 1 d . . .
C14 C 0.32650(11) 0.05123(14) 0.33484(15) 0.0371(4) Uani 1 1 d . . .
H14 H 0.3493 -0.0071 0.3313 0.044 Uiso 1 1 calc R . .
C15 C 0.31792(11) 0.06508(14) 0.40353(15) 0.0369(4) Uani 1 1 d . . .
H15 H 0.3331 0.0189 0.4554 0.044 Uiso 1 1 calc R . .
C16 C 0.23408(12) 0.14381(14) 0.47148(15) 0.0362(4) Uani 1 1 d . . .
H16 H 0.2232 0.0730 0.4521 0.043 Uiso 1 1 calc R . .
C17 C 0.26424(10) 0.20785(13) 0.44008(13) 0.0298(4) Uani 1 1 d . . .
C18 C 0.27972(11) 0.31383(14) 0.46822(15) 0.0363(4) Uani 1 1 d . . .
H18 H 0.2995 0.3565 0.4464 0.044 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 O3 1.9576(14) 8_556 ?
Cu1 O1W 1.9587(15) . ?
Cu1 O2 1.9873(13) . ?
Cu1 N1 1.9893(18) . ?
O1 C2 1.251(2) . ?
O2 C2 1.273(2) . ?
O3 C9 1.278(2) . ?
O3 Cu1 1.9577(14) 8_455 ?
O4 C9 1.238(2) . ?
O5 C7 1.371(2) . ?
O5 C10 1.431(2) . ?
N1 C13 1.320(2) . ?
N1 C14 1.382(2) . ?
N2 C13 1.363(2) . ?
N2 C15 1.387(2) . ?
N2 C17 1.430(2) . ?
C2 C3 1.504(2) . ?
C3 C4 1.385(2) . ?
C3 C8 1.398(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.392(3) . ?
C5 C9 1.507(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.390(2) . ?
C10 C11 1.510(3) . ?
C12 C13 1.486(3) . ?
C14 C15 1.339(3) . ?
C16 C18 1.382(3) 7_556 ?
C16 C17 1.388(3) . ?
C17 C18 1.388(2) . ?
C18 C16 1.382(3) 7_556 ?

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 O1W 89.40(6) 8_556 . ?
O3 Cu1 O2 176.79(5) 8_556 . ?
O1W Cu1 O2 90.11(6) . . ?
O3 Cu1 N1 90.81(6) 8_556 . ?
O1W Cu1 N1 168.22(6) . . ?
O2 Cu1 N1 90.32(6) . . ?
C2 O2 Cu1 106.28(11) . . ?
C9 O3 Cu1 121.80(12) . 8_455 ?
C7 O5 C10 117.82(14) . . ?
C13 N1 C14 106.90(16) . . ?
C13 N1 Cu1 129.27(12) . . ?
C14 N1 Cu1 123.78(12) . . ?
C13 N2 C15 107.20(15) . . ?
C13 N2 C17 128.45(15) . . ?
C15 N2 C17 124.33(15) . . ?
O1 C2 O2 122.38(15) . . ?
O1 C2 C3 119.30(15) . . ?
O2 C2 C3 118.32(15) . . ?
C4 C3 C8 120.16(15) . . ?
C4 C3 C2 119.45(15) . . ?
C8 C3 C2 120.37(15) . . ?
C3 C4 C5 119.89(15) . . ?
C6 C5 C4 120.00(15) . . ?
C6 C5 C9 118.69(15) . . ?
C4 C5 C9 121.21(16) . . ?
C5 C6 C7 120.18(16) . . ?
O5 C7 C8 124.76(15) . . ?
O5 C7 C6 115.64(15) . . ?
C8 C7 C6 119.61(16) . . ?
C7 C8 C3 120.12(15) . . ?
O4 C9 O3 125.73(16) . . ?
O4 C9 C5 118.50(16) . . ?
O3 C9 C5 115.73(15) . . ?
O5 C10 C11 107.02(16) . . ?
N1 C13 N2 109.83(15) . . ?
N1 C13 C12 125.25(17) . . ?
N2 C13 C12 124.90(17) . . ?
C15 C14 N1 109.54(16) . . ?
C14 C15 N2 106.52(16) . . ?
C18 C16 C17 119.44(16) 7_556 . ?
C16 C17 C18 120.26(17) . . ?
C16 C17 N2 118.93(15) . . ?
C18 C17 N2 120.76(16) . . ?
C16 C18 C17 120.30(17) 7_556 . ?

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
O1W H6A O1 0.85 1.83 2.6569(19) 163.2 7
O1W H6B O4 0.85 1.78 2.615(2) 166.6 2_554

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.233
_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_w
_audit_block_doi                 10.5517/cc141fk5
_database_code_depnum_ccdc_archive 'CCDC 1044066'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15.50 Cu0.50 N2.50 O3'
_chemical_formula_weight         322.58

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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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, 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                   12.725(5)
_cell_length_b                   18.008(8)
_cell_length_c                   13.521(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3098(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.757
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21554
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.155
_diffrn_reflns_theta_max         27.570
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3667
_reflns_number_gt                3044
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0474P)²+2.6837P]
 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         3667
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.5000 0.5000 0.0000 0.03006(13) Uani 1 2 d S . P . .
O1 O 0.52974(13) 0.60906(9) 0.00954(11) 0.0363(4) Uani 1 1 d . . . . .
O2 O 0.67769(14) 0.55396(9) -0.03466(15) 0.0490(4) Uani 1 1 d . . . . .
O3 O 0.9529(2) 0.7500 0.0277(3) 0.0900(12) Uani 1 2 d S T P . .
O22 O 0.6776(4) 0.6648(3) -0.2780(4) 0.0901(16) Uani 0.5 1 d . . P . .
N1 N 0.54707(15) 0.48676(10) 0.13831(13) 0.0336(4) Uani 1 1 d . . . . .
N2 N 0.55360(15) 0.48649(11) 0.29984(13) 0.0364(4) Uani 1 1 d . . . . .
N3 N 0.5490(3) 0.7500 -0.2469(3) 0.0702(10) Uani 1 2 d S T P . .
C1 C 0.62744(18) 0.61018(12) -0.00966(15) 0.0347(5) Uani 1 1 d . . . . .
C2 C 0.68365(17) 0.68348(12) -0.00147(16) 0.0333(5) Uani 1 1 d . . . . .
C3 C 0.6289(2) 0.7500 -0.0026(2) 0.0343(7) Uani 1 2 d S T P . .
H3 H 0.5559 0.7500 -0.0041 0.041 Uiso 1 2 calc R U P . .
C4 C 0.79262(19) 0.68331(13) 0.00654(18) 0.0410(5) Uani 1 1 d . . . . .
H4 H 0.8293 0.6386 0.0071 0.049 Uiso 1 1 calc R U . . .
C5 C 0.8463(3) 0.7500 0.0137(3) 0.0449(8) Uani 1 2 d S T P . .
C6 C 1.0126(4) 0.6992(3) 0.0435(7) 0.076(2) Uani 0.5 1 d . . P . .
C7 C 1.1182(4) 0.7212(3) 0.0840(5) 0.0511(13) Uani 0.5 1 d . . P . .
C8 C 1.1302(6) 0.7500 0.1783(6) 0.128(3) Uani 1 2 d S T P . .
H8A H 1.0707 0.7692 0.2137 0.154 Uiso 0.5 1 d R U P . .
C9 C 1.2310(8) 0.7500 0.2168(6) 0.153(4) Uani 1 2 d S T P . .
H9A H 1.2382 0.7500 0.2875 0.183 Uiso 1 2 d R U P . .
C10 C 1.3137(5) 0.7500 0.1595(8) 0.110(3) Uani 1 2 d S T P . .
H10A H 1.3806 0.7655 0.1850 0.132 Uiso 0.5 1 d R U P . .
C11 C 1.3015(5) 0.7269(4) 0.0673(8) 0.095(3) Uani 0.5 1 d . . P . .
H11A H 1.3626 0.7189 0.0271 0.114 Uiso 0.5 1 d R U P . .
C12 C 1.2049(6) 0.7151(5) 0.0288(6) 0.084(2) Uani 0.5 1 d . . P . .
H12A H 1.1972 0.7026 -0.0398 0.100 Uiso 0.5 1 d R U P . .
C13 C 0.4047(2) 0.55751(16) 0.22166(19) 0.0540(7) Uani 1 1 d . . . . .
H13A H 0.4043 0.5896 0.1649 0.081 Uiso 1 1 calc R U . . .
H13B H 0.4049 0.5870 0.2808 0.081 Uiso 1 1 calc R U . . .
H13C H 0.3431 0.5267 0.2207 0.081 Uiso 1 1 calc R U . . .
C14 C 0.49957(18) 0.51026(12) 0.21937(18) 0.0358(5) Uani 1 1 d . . . . .
C15 C 0.63419(19) 0.44772(14) 0.16758(17) 0.0415(5) Uani 1 1 d . . . . .
H15 H 0.6818 0.4249 0.1251 0.050 Uiso 1 1 calc R U . . .
C16 C 0.64049(18) 0.44729(14) 0.26667(17) 0.0418(5) Uani 1 1 d . . . . .
H16 H 0.6924 0.4252 0.3051 0.050 Uiso 1 1 calc R U . . .
C17 C 0.52573(19) 0.49475(11) 0.40196(17) 0.0344(5) Uani 1 1 d . . . . .
C18 C 0.59994(19) 0.51909(15) 0.46824(18) 0.0415(5) Uani 1 1 d . . . . .
H18 H 0.6670 0.5318 0.4468 0.050 Uiso 1 1 calc R U . . .
C19 C 0.57392(19) 0.52442(15) 0.56710(17) 0.0422(5) Uani 1 1 d . . . . .
H19 H 0.6234 0.5409 0.6127 0.051 Uiso 1 1 calc R U . . .
C20 C 0.4427(5) 0.7500 -0.2069(6) 0.111(2) Uani 1 2 d S T P . .
H20A H 0.4363 0.7114 -0.1583 0.167 Uiso 0.5 1 calc R U P . .
H20B H 0.3933 0.7414 -0.2593 0.167 Uiso 0.5 1 calc R U P . .
H20C H 0.4285 0.7972 -0.1767 0.167 Uiso 0.5 1 calc R U P . .
C21 C 0.5954(4) 0.6817(2) -0.2586(5) 0.1164(17) 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 N1 1.978(2) . ?
Cu1 N1 1.978(2) 5_665 ?
Cu1 O1 2.0042(18) . ?
Cu1 O1 2.0043(18) 5_665 ?
O1 C1 1.270(3) . ?
O2 C1 1.244(3) . ?
O3 C6 1.208(6) . ?
O3 C6 1.208(6) 8_575 ?
O3 C5 1.370(4) . ?
O22 C21 1.121(6) . ?
N1 C14 1.321(3) . ?
N1 C15 1.371(3) . ?
N2 C14 1.356(3) . ?
N2 C16 1.386(3) . ?
N2 C17 1.433(3) . ?
N3 C21 1.373(5) . ?
N3 C21 1.373(5) 8_575 ?
N3 C20 1.456(7) . ?
C1 C2 1.506(3) . ?
C2 C3 1.386(3) . ?
C2 C4 1.391(3) . ?
C3 C2 1.386(3) 8_575 ?
C4 C5 1.385(3) . ?
C5 C4 1.385(3) 8_575 ?
C6 C7 1.504(7) . ?
C6 C6 1.829(12) 8_575 ?
C6 C7 2.039(8) 8_575 ?
C7 C7 1.036(10) 8_575 ?
C7 C12 1.337(9) . ?
C7 C8 1.384(8) . ?
C7 C12 1.758(9) 8_575 ?
C7 C6 2.039(8) 8_575 ?
C8 C7 1.384(8) 8_575 ?
C8 C9 1.384(10) . ?
C9 C10 1.307(11) . ?
C10 C11 1.323(11) 8_575 ?
C10 C11 1.323(11) . ?
C11 C11 0.833(15) 8_575 ?
C11 C12 1.351(10) . ?
C11 C12 1.695(10) 8_575 ?
C12 C12 1.258(16) 8_575 ?
C12 C11 1.695(10) 8_575 ?
C12 C7 1.758(9) 8_575 ?
C13 C14 1.478(3) . ?
C15 C16 1.342(3) . ?
C17 C18 1.374(3) . ?
C17 C19 1.379(3) 5_666 ?
C18 C19 1.380(3) . ?
C19 C17 1.379(3) 5_666 ?

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
N1 Cu1 N1 180.0 . 5_665 ?
N1 Cu1 O1 90.00(7) . . ?
N1 Cu1 O1 89.99(7) 5_665 . ?
N1 Cu1 O1 90.00(7) . 5_665 ?
N1 Cu1 O1 90.01(7) 5_665 5_665 ?
O1 Cu1 O1 180.0 . 5_665 ?
C1 O1 Cu1 100.79(14) . . ?
C6 O3 C6 98.4(6) . 8_575 ?
C6 O3 C5 130.3(3) . . ?
C6 O3 C5 130.3(3) 8_575 . ?
C14 N1 C15 107.14(19) . . ?
C14 N1 Cu1 127.38(16) . . ?
C15 N1 Cu1 125.42(15) . . ?
C14 N2 C16 107.78(19) . . ?
C14 N2 C17 127.9(2) . . ?
C16 N2 C17 124.19(19) . . ?
C21 N3 C21 127.1(6) . 8_575 ?
C21 N3 C20 116.2(3) . . ?
C21 N3 C20 116.2(3) 8_575 . ?
O2 C1 O1 123.1(2) . . ?
O2 C1 C2 119.3(2) . . ?
O1 C1 C2 117.64(19) . . ?
C3 C2 C4 120.2(2) . . ?
C3 C2 C1 121.2(2) . . ?
C4 C2 C1 118.5(2) . . ?
C2 C3 C2 119.7(3) 8_575 . ?
C5 C4 C2 119.7(2) . . ?
O3 C5 C4 119.89(16) . 8_575 ?
O3 C5 C4 119.89(16) . . ?
C4 C5 C4 120.2(3) 8_575 . ?
O3 C6 C7 115.2(5) . . ?
O3 C6 C6 40.8(3) . 8_575 ?
C7 C6 C6 74.7(3) . 8_575 ?
O3 C6 C7 86.0(4) . 8_575 ?
C7 C6 C7 29.4(3) . 8_575 ?
C6 C6 C7 45.4(2) 8_575 8_575 ?
C7 C7 C12 94.8(4) 8_575 . ?
C7 C7 C8 68.0(2) 8_575 . ?
C12 C7 C8 117.0(6) . . ?
C7 C7 C6 105.3(3) 8_575 . ?
C12 C7 C6 120.8(6) . . ?
C8 C7 C6 122.2(6) . . ?
C7 C7 C12 49.3(3) 8_575 8_575 ?
C12 C7 C12 45.5(6) . 8_575 ?
C8 C7 C12 94.4(4) . 8_575 ?
C6 C7 C12 125.3(6) . 8_575 ?
C7 C7 C6 45.4(2) 8_575 8_575 ?
C12 C7 C6 116.9(6) . 8_575 ?
C8 C7 C6 93.3(4) . 8_575 ?
C6 C7 C6 59.9(4) . 8_575 ?
C12 C7 C6 80.9(4) 8_575 8_575 ?
C7 C8 C7 43.9(5) 8_575 . ?
C7 C8 C9 116.7(6) 8_575 . ?
C7 C8 C9 116.7(6) . . ?
C10 C9 C8 121.5(7) . . ?
C9 C10 C11 117.6(6) . 8_575 ?
C9 C10 C11 117.6(6) . . ?
C11 C10 C11 36.7(7) 8_575 . ?
C11 C11 C10 71.6(4) 8_575 . ?
C11 C11 C12 99.0(5) 8_575 . ?
C10 C11 C12 121.2(7) . . ?
C11 C11 C12 51.9(4) 8_575 8_575 ?
C10 C11 C12 100.4(6) . 8_575 ?
C12 C11 C12 47.1(7) . 8_575 ?
C12 C12 C7 85.2(4) 8_575 . ?
C12 C12 C11 81.0(5) 8_575 . ?
C7 C12 C11 121.6(7) . . ?
C12 C12 C11 51.9(4) 8_575 8_575 ?
C7 C12 C11 112.1(6) . 8_575 ?
C11 C12 C11 29.0(5) . 8_575 ?
C12 C12 C7 49.3(3) 8_575 8_575 ?
C7 C12 C7 36.0(4) . 8_575 ?
C11 C12 C7 107.8(6) . 8_575 ?
C11 C12 C7 85.6(5) 8_575 8_575 ?
N1 C14 N2 109.4(2) . . ?
N1 C14 C13 125.2(2) . . ?
N2 C14 C13 125.4(2) . . ?
C16 C15 N1 109.8(2) . . ?
C15 C16 N2 105.8(2) . . ?
C18 C17 C19 120.9(2) . 5_666 ?
C18 C17 N2 119.4(2) . . ?
C19 C17 N2 119.6(2) 5_666 . ?
C17 C18 C19 119.3(2) . . ?
C17 C19 C18 119.8(2) 5_666 . ?
O22 C21 N3 132.2(6) . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_d
_audit_block_doi                 10.5517/cc141gc0
_database_code_depnum_ccdc_archive 'CCDC 1044091'
_audit_update_record             
;
2015-01-19 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H29 Cu N4 O7.50'
_chemical_formula_weight         569.06

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.751(2)
_cell_length_b                   12.916(3)
_cell_length_c                   14.603(4)
_cell_angle_alpha                83.875(6)
_cell_angle_beta                 88.192(7)
_cell_angle_gamma                74.126(6)
_cell_volume                     1398.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11757
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         27.47
_reflns_number_total             6181
_reflns_number_gt                4404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0976P)²+0.2721P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6181
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1708
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.003

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 0.5000 0.5000 1.0000 0.03036(19) Uani 1 2 d S . .
Cu2 Cu 1.0000 0.0000 0.5000 0.03171(19) Uani 1 2 d S . .
O1 O 0.5993(4) 0.4994(2) 0.87327(16) 0.0395(6) Uani 1 1 d . . .
O2 O 0.5784(4) 0.3318(2) 0.90120(19) 0.0486(7) Uani 1 1 d . . .
O3 O 0.8392(4) 0.0791(2) 0.6557(2) 0.0532(8) Uani 1 1 d . . .
O4 O 0.9314(4) 0.1511(2) 0.52610(17) 0.0393(6) Uani 1 1 d . . .
O5 O 0.7124(5) 0.5564(2) 0.54093(18) 0.0524(8) Uani 1 1 d . . .
N1 N 0.2581(4) 0.5368(3) 0.9443(2) 0.0384(7) Uani 1 1 d . . .
N2 N 0.0145(5) 0.6177(3) 0.8674(2) 0.0444(8) Uani 1 1 d . . .
N3 N -0.5299(5) 0.9154(3) 0.6548(2) 0.0447(8) Uani 1 1 d . . .
N4 N -0.7731(4) 0.9761(3) 0.5714(2) 0.0371(7) Uani 1 1 d . . .
C1 C 0.6127(5) 0.4055(3) 0.8492(2) 0.0359(8) Uani 1 1 d . . .
C2 C 0.6721(5) 0.3881(3) 0.7514(2) 0.0341(8) Uani 1 1 d . . .
C3 C 0.7329(5) 0.2847(3) 0.7237(3) 0.0372(8) Uani 1 1 d . . .
H3 H 0.7340 0.2248 0.7654 0.045 Uiso 1 1 calc R . .
C4 C 0.7916(5) 0.2705(3) 0.6351(2) 0.0341(8) Uani 1 1 d . . .
C5 C 0.8591(5) 0.1582(3) 0.6051(3) 0.0353(8) Uani 1 1 d . . .
C6 C 0.7861(5) 0.3589(3) 0.5717(2) 0.0363(8) Uani 1 1 d . . .
H6 H 0.8240 0.3486 0.5114 0.044 Uiso 1 1 calc R . .
C7 C 0.7242(5) 0.4626(3) 0.5978(3) 0.0383(9) Uani 1 1 d . . .
C8 C 0.6678(5) 0.4775(3) 0.6880(2) 0.0383(9) Uani 1 1 d . . .
H8 H 0.6274 0.5470 0.7060 0.046 Uiso 1 1 calc R . .
C9 C 0.7542(6) 0.5479(3) 0.4463(3) 0.0446(10) Uani 1 1 d . . .
H9A H 0.6748 0.5137 0.4186 0.054 Uiso 1 1 calc R . .
H9B H 0.8769 0.5050 0.4390 0.054 Uiso 1 1 calc R . .
C10 C 0.7296(7) 0.6623(4) 0.4014(3) 0.0539(11) Uani 1 1 d . . .
H10A H 0.8046 0.6964 0.4327 0.065 Uiso 1 1 calc R . .
H10B H 0.6058 0.7033 0.4088 0.065 Uiso 1 1 calc R . .
C11 C 0.7770(8) 0.6666(5) 0.2989(3) 0.0743(16) Uani 1 1 d . . .
H11A H 0.9029 0.6335 0.2915 0.111 Uiso 1 1 calc R . .
H11B H 0.7485 0.7407 0.2727 0.111 Uiso 1 1 calc R . .
H11C H 0.7094 0.6285 0.2682 0.111 Uiso 1 1 calc R . .
C12 C 0.1957(8) 0.7386(4) 0.9128(4) 0.0748(17) Uani 1 1 d . . .
H12A H 0.1504 0.7674 0.9694 0.112 Uiso 1 1 calc R . .
H12B H 0.1381 0.7876 0.8617 0.112 Uiso 1 1 calc R . .
H12C H 0.3228 0.7296 0.9093 0.112 Uiso 1 1 calc R . .
C13 C 0.1585(6) 0.6322(4) 0.9097(3) 0.0439(10) Uani 1 1 d . . .
C14 C 0.1773(5) 0.4595(3) 0.9237(3) 0.0425(9) Uani 1 1 d . . .
H14 H 0.2198 0.3854 0.9402 0.051 Uiso 1 1 calc R . .
C15 C 0.0259(6) 0.5091(4) 0.8755(3) 0.0451(10) Uani 1 1 d . . .
H15 H -0.0543 0.4763 0.8525 0.054 Uiso 1 1 calc R . .
C16 C -0.1215(6) 0.7000(4) 0.8131(3) 0.0457(10) Uani 1 1 d . . .
C17 C -0.2341(7) 0.7836(4) 0.8529(3) 0.0714(17) Uani 1 1 d . . .
H17 H -0.2199 0.7921 0.9144 0.086 Uiso 1 1 calc R . .
C18 C -0.3702(7) 0.8561(4) 0.8010(3) 0.0724(17) Uani 1 1 d . . .
H18 H -0.4488 0.9133 0.8274 0.087 Uiso 1 1 calc R . .
C19 C -0.3870(6) 0.8422(3) 0.7107(3) 0.0442(10) Uani 1 1 d . . .
C20 C -0.2734(6) 0.7585(4) 0.6705(3) 0.0503(11) Uani 1 1 d . . .
H20 H -0.2863 0.7501 0.6089 0.060 Uiso 1 1 calc R . .
C21 C -0.1389(6) 0.6866(4) 0.7235(3) 0.0501(11) Uani 1 1 d . . .
H21 H -0.0605 0.6290 0.6976 0.060 Uiso 1 1 calc R . .
C22 C -0.7057(7) 0.7831(4) 0.6408(3) 0.0668(16) Uani 1 1 d . . .
H22A H -0.8324 0.7908 0.6403 0.100 Uiso 1 1 calc R . .
H22B H -0.6579 0.7513 0.7003 0.100 Uiso 1 1 calc R . .
H22C H -0.6481 0.7373 0.5948 0.100 Uiso 1 1 calc R . .
C23 C -0.6727(6) 0.8905(3) 0.6207(3) 0.0404(9) Uani 1 1 d . . .
C24 C -0.6905(6) 1.0577(3) 0.5744(3) 0.0537(12) Uani 1 1 d . . .
H24 H -0.7324 1.1274 0.5451 0.064 Uiso 1 1 calc R . .
C25 C -0.5403(6) 1.0222(4) 0.6259(4) 0.0585(13) Uani 1 1 d . . .
H25 H -0.4611 1.0612 0.6390 0.070 Uiso 1 1 calc R . .
O1W O 0.2692(11) 0.0374(7) 0.9360(6) 0.227(4) Uani 1 1 d . . .
O2W O 0.9676(9) 0.0099(4) 0.8413(4) 0.142(2) Uani 1 1 d . . .
O3W O 0.5653(13) 0.1156(5) 0.9236(5) 0.083(3) Uani 0.50 1 d 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 O1 1.982(2) . ?
Cu1 O1 1.982(2) 2_667 ?
Cu1 N1 1.982(3) . ?
Cu1 N1 1.982(3) 2_667 ?
Cu2 O4 1.953(2) 2_756 ?
Cu2 O4 1.953(2) . ?
Cu2 N4 2.006(3) 2_566 ?
Cu2 N4 2.006(3) 1_745 ?
O1 C1 1.275(5) . ?
O2 C1 1.236(5) . ?
O3 C5 1.237(5) . ?
O4 C5 1.267(5) . ?
O5 C7 1.377(4) . ?
O5 C9 1.418(5) . ?
N1 C13 1.319(5) . ?
N1 C14 1.379(5) . ?
N2 C13 1.359(5) . ?
N2 C15 1.373(6) . ?
N2 C16 1.459(5) . ?
N3 C23 1.356(5) . ?
N3 C25 1.380(6) . ?
N3 C19 1.451(5) . ?
N4 C23 1.319(5) . ?
N4 C24 1.380(5) . ?
N4 Cu2 2.006(3) 1_365 ?
C1 C2 1.507(5) . ?
C2 C3 1.388(5) . ?
C2 C8 1.394(5) . ?
C3 C4 1.373(5) . ?
C4 C6 1.383(5) . ?
C4 C5 1.509(5) . ?
C6 C7 1.384(5) . ?
C7 C8 1.391(5) . ?
C9 C10 1.515(6) . ?
C10 C11 1.529(6) . ?
C12 C13 1.485(6) . ?
C14 C15 1.352(6) . ?
C16 C21 1.353(6) . ?
C16 C17 1.361(6) . ?
C17 C18 1.386(6) . ?
C18 C19 1.365(6) . ?
C19 C20 1.367(6) . ?
C20 C21 1.384(6) . ?
C22 C23 1.476(6) . ?
C24 C25 1.349(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 O1 179.999(1) . 2_667 ?
O1 Cu1 N1 87.69(12) . . ?
O1 Cu1 N1 92.31(12) 2_667 . ?
O1 Cu1 N1 92.31(12) . 2_667 ?
O1 Cu1 N1 87.69(12) 2_667 2_667 ?
N1 Cu1 N1 180.00(8) . 2_667 ?
O4 Cu2 O4 179.999(1) 2_756 . ?
O4 Cu2 N4 89.26(11) 2_756 2_566 ?
O4 Cu2 N4 90.74(11) . 2_566 ?
O4 Cu2 N4 90.74(11) 2_756 1_745 ?
O4 Cu2 N4 89.26(11) . 1_745 ?
N4 Cu2 N4 180.00(15) 2_566 1_745 ?
C1 O1 Cu1 106.3(2) . . ?
C5 O4 Cu2 109.4(2) . . ?
C7 O5 C9 118.1(3) . . ?
C13 N1 C14 108.0(3) . . ?
C13 N1 Cu1 128.5(3) . . ?
C14 N1 Cu1 122.8(3) . . ?
C13 N2 C15 108.7(3) . . ?
C13 N2 C16 126.9(4) . . ?
C15 N2 C16 124.1(3) . . ?
C23 N3 C25 108.6(3) . . ?
C23 N3 C19 126.2(4) . . ?
C25 N3 C19 125.2(4) . . ?
C23 N4 C24 106.3(3) . . ?
C23 N4 Cu2 132.3(3) . 1_365 ?
C24 N4 Cu2 121.3(3) . 1_365 ?
O2 C1 O1 123.3(3) . . ?
O2 C1 C2 120.5(3) . . ?
O1 C1 C2 116.2(3) . . ?
C3 C2 C8 119.5(3) . . ?
C3 C2 C1 121.2(3) . . ?
C8 C2 C1 119.3(3) . . ?
C4 C3 C2 120.2(4) . . ?
C3 C4 C6 120.5(3) . . ?
C3 C4 C5 120.3(3) . . ?
C6 C4 C5 119.2(3) . . ?
O3 C5 O4 123.3(3) . . ?
O3 C5 C4 120.3(4) . . ?
O4 C5 C4 116.4(3) . . ?
C4 C6 C7 120.1(3) . . ?
O5 C7 C6 125.3(3) . . ?
O5 C7 C8 115.0(3) . . ?
C6 C7 C8 119.7(3) . . ?
C7 C8 C2 120.0(3) . . ?
O5 C9 C10 106.5(3) . . ?
C9 C10 C11 112.9(4) . . ?
N1 C13 N2 108.5(4) . . ?
N1 C13 C12 127.1(4) . . ?
N2 C13 C12 124.5(4) . . ?
C15 C14 N1 108.7(4) . . ?
C14 C15 N2 106.1(4) . . ?
C21 C16 C17 121.3(4) . . ?
C21 C16 N2 117.7(4) . . ?
C17 C16 N2 120.9(4) . . ?
C16 C17 C18 119.5(4) . . ?
C19 C18 C17 119.0(4) . . ?
C18 C19 C20 121.6(4) . . ?
C18 C19 N3 120.4(4) . . ?
C20 C19 N3 118.0(4) . . ?
C19 C20 C21 118.6(4) . . ?
C16 C21 C20 120.1(4) . . ?
N4 C23 N3 109.7(3) . . ?
N4 C23 C22 127.6(4) . . ?
N3 C23 C22 122.7(4) . . ?
C25 C24 N4 110.4(4) . . ?
C24 C25 N3 105.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.920
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.086
