# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_111021d
_database_code_depnum_ccdc_archive 'CCDC 996766'
_audit_update_record             
;
2014-04-11 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 Cu N4 O6'
_chemical_formula_weight         385.82

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   Pbca

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

_cell_length_a                   19.4754(18)
_cell_length_b                   7.2595(5)
_cell_length_c                   22.789(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3222.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1492
_cell_measurement_theta_min      3.126
_cell_measurement_theta_max      18.179

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
_exptl_absorpt_coefficient_mu    1.393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5728
_exptl_absorpt_correction_T_max  0.8506
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            14980
_diffrn_reflns_av_R_equivalents  0.2228
_diffrn_reflns_av_sigmaI/netI    0.1477
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2797
_reflns_number_gt                1520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1036P)²+46.8153P] 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         2797
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2053
_refine_ls_R_factor_gt           0.1431
_refine_ls_wR_factor_ref         0.3247
_refine_ls_wR_factor_gt          0.2969
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.55183(8) 0.1887(3) 0.39825(7) 0.0487(6) Uani 1 1 d . A .
N1 N 0.4911(6) 0.0969(18) 0.3333(5) 0.046(3) Uani 1 1 d . . .
N2 N 0.6412(6) 0.2008(17) 0.3540(5) 0.048(3) Uani 1 1 d . . .
N3 N 0.6096(6) 0.2956(17) 0.4613(5) 0.047(3) Uani 1 1 d . . .
N4 N 0.5162(7) 0.598(2) 0.3237(6) 0.059(4) Uani 1 1 d . A .
O1 O 0.4712(5) 0.1791(15) 0.4462(4) 0.050(2) Uani 1 1 d . . .
O2 O 0.3624(5) 0.0848(17) 0.4479(5) 0.065(3) Uani 1 1 d . . .
O3 O 0.5909(5) -0.1206(15) 0.4275(4) 0.057(3) Uani 1 1 d . . .
H3F H 0.6023 -0.1277 0.4635 0.068 Uiso 1 1 d R A .
H3G H 0.5744 -0.2238 0.4169 0.068 Uiso 1 1 d R . .
O4 O 0.5312(6) 0.5491(16) 0.3731(5) 0.065(3) Uani 1 1 d . . .
O5 O 0.4672(7) 0.511(2) 0.3011(6) 0.088(4) Uani 1 1 d . . .
O6 O 0.5422(7) 0.7211(19) 0.2971(5) 0.081(4) Uani 1 1 d . . .
C1 C 0.4174(8) 0.108(2) 0.4206(7) 0.052(4) Uani 1 1 d . A .
C2 C 0.419(3) 0.112(14) 0.354(2) 0.053(13) Uani 0.59(13) 1 d P A 1
H2 H 0.4017 0.2320 0.3418 0.064 Uiso 0.59(13) 1 calc PR A 1
C3 C 0.375(6) -0.036(13) 0.325(5) 0.059(18) Uani 0.59(13) 1 d P A 1
H3A H 0.4035 -0.1398 0.3150 0.088 Uiso 0.59(13) 1 calc PR A 1
H3B H 0.3550 0.0136 0.2899 0.088 Uiso 0.59(13) 1 calc PR A 1
H3C H 0.3396 -0.0743 0.3514 0.088 Uiso 0.59(13) 1 calc PR A 1
C2' C 0.429(4) 0.019(18) 0.362(4) 0.053(18) Uani 0.41(13) 1 d P A 2
H2' H 0.4378 -0.1122 0.3687 0.064 Uiso 0.41(13) 1 calc PR A 2
C3' C 0.366(8) 0.035(18) 0.322(7) 0.06(3) Uani 0.41(13) 1 d P A 2
H3'1 H 0.3449 0.1531 0.3277 0.088 Uiso 0.41(13) 1 calc PR A 2
H3'2 H 0.3337 -0.0603 0.3322 0.088 Uiso 0.41(13) 1 calc PR A 2
H3'3 H 0.3796 0.0212 0.2820 0.088 Uiso 0.41(13) 1 calc PR A 2
C4 C 0.6546(8) 0.146(2) 0.2982(6) 0.052(4) Uani 1 1 d . A .
H4 H 0.6188 0.1085 0.2739 0.063 Uiso 1 1 calc R . .
C5 C 0.7189(8) 0.145(2) 0.2782(8) 0.061(4) Uani 1 1 d . . .
H5 H 0.7267 0.1134 0.2392 0.073 Uiso 1 1 calc R A .
C6 C 0.7728(8) 0.188(2) 0.3124(7) 0.060(4) Uani 1 1 d . A .
H6 H 0.8173 0.1804 0.2978 0.072 Uiso 1 1 calc R . .
C7 C 0.7615(8) 0.242(2) 0.3687(7) 0.052(4) Uani 1 1 d . . .
H7 H 0.7981 0.2719 0.3930 0.062 Uiso 1 1 calc R A .
C8 C 0.6958(7) 0.251(2) 0.3890(7) 0.049(4) Uani 1 1 d . A .
C9 C 0.6775(7) 0.307(2) 0.4479(6) 0.050(4) Uani 1 1 d . A .
C10 C 0.7222(8) 0.381(2) 0.4878(7) 0.056(4) Uani 1 1 d . . .
H10 H 0.7685 0.3912 0.4783 0.067 Uiso 1 1 calc R A .
C11 C 0.6994(8) 0.441(2) 0.5422(7) 0.058(4) Uani 1 1 d . A .
H11 H 0.7299 0.4920 0.5692 0.070 Uiso 1 1 calc R . .
C12 C 0.6288(9) 0.424(2) 0.5556(8) 0.060(4) Uani 1 1 d . . .
H12 H 0.6114 0.4579 0.5920 0.072 Uiso 1 1 calc R A .
C13 C 0.5875(8) 0.355(2) 0.5126(7) 0.055(4) Uani 1 1 d . A .
H13 H 0.5405 0.3502 0.5199 0.066 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 1.915(9) . ?
Cu1 N3 1.982(11) . ?
Cu1 N1 2.008(11) . ?
Cu1 N2 2.014(11) . ?
Cu1 O3 2.464(11) . ?
Cu1 O4 2.708(12) . ?
N1 C2' 1.48(8) . ?
N1 C2 1.48(5) . ?
N2 C4 1.359(18) . ?
N2 C8 1.377(17) . ?
N3 C13 1.320(19) . ?
N3 C9 1.360(18) . ?
N4 O6 1.195(18) . ?
N4 O4 1.215(15) . ?
N4 O5 1.256(17) . ?
O1 C1 1.304(17) . ?
O2 C1 1.250(17) . ?
O3 H3F 0.8499 . ?
O3 H3G 0.8500 . ?
C1 C2' 1.50(8) . ?
C1 C2 1.51(6) . ?
C2 C3 1.53(15) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C2' C3' 1.5(2) . ?
C2' H2' 0.9800 . ?
C3' H3'1 0.9600 . ?
C3' H3'2 0.9600 . ?
C3' H3'3 0.9600 . ?
C4 C5 1.33(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.35(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.36(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.362(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.45(2) . ?
C9 C10 1.37(2) . ?
C10 C11 1.39(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.42(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.36(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

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 N3 93.8(5) . . ?
O1 Cu1 N1 85.7(4) . . ?
N3 Cu1 N1 176.3(5) . . ?
O1 Cu1 N2 175.2(4) . . ?
N3 Cu1 N2 81.7(5) . . ?
N1 Cu1 N2 98.9(5) . . ?
O1 Cu1 O3 93.8(4) . . ?
N3 Cu1 O3 89.1(4) . . ?
N1 Cu1 O3 94.6(4) . . ?
N2 Cu1 O3 84.7(4) . . ?
O1 Cu1 O4 92.0(4) . . ?
N3 Cu1 O4 81.9(4) . . ?
N1 Cu1 O4 94.5(4) . . ?
N2 Cu1 O4 88.9(4) . . ?
O3 Cu1 O4 169.7(3) . . ?
C2' N1 C2 28(3) . . ?
C2' N1 Cu1 106(3) . . ?
C2 N1 Cu1 107(2) . . ?
C4 N2 C8 118.2(12) . . ?
C4 N2 Cu1 128.4(10) . . ?
C8 N2 Cu1 112.9(9) . . ?
C13 N3 C9 119.7(13) . . ?
C13 N3 Cu1 125.9(10) . . ?
C9 N3 Cu1 114.4(10) . . ?
O6 N4 O4 125.8(15) . . ?
O6 N4 O5 119.3(15) . . ?
O4 N4 O5 114.8(15) . . ?
C1 O1 Cu1 114.7(9) . . ?
Cu1 O3 H3F 113.3 . . ?
Cu1 O3 H3G 127.5 . . ?
H3F O3 H3G 108.7 . . ?
N4 O4 Cu1 120.7(10) . . ?
O2 C1 O1 121.2(13) . . ?
O2 C1 C2' 121(3) . . ?
O1 C1 C2' 116(3) . . ?
O2 C1 C2 121(2) . . ?
O1 C1 C2 115(2) . . ?
C2' C1 C2 28(3) . . ?
N1 C2 C1 110(4) . . ?
N1 C2 C3 110(6) . . ?
C1 C2 C3 114(7) . . ?
N1 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
C3 C2 H2 107.5 . . ?
N1 C2' C1 111(5) . . ?
N1 C2' C3' 112(9) . . ?
C1 C2' C3' 112(10) . . ?
N1 C2' H2' 107.6 . . ?
C1 C2' H2' 107.6 . . ?
C3' C2' H2' 107.6 . . ?
C2' C3' H3'1 109.5 . . ?
C2' C3' H3'2 109.5 . . ?
H3'1 C3' H3'2 109.5 . . ?
C2' C3' H3'3 109.5 . . ?
H3'1 C3' H3'3 109.5 . . ?
H3'2 C3' H3'3 109.5 . . ?
C5 C4 N2 120.1(15) . . ?
C5 C4 H4 119.9 . . ?
N2 C4 H4 119.9 . . ?
C4 C5 C6 122.3(16) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C7 119.2(15) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C8 119.2(15) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 N2 121.0(14) . . ?
C7 C8 C9 124.1(14) . . ?
N2 C8 C9 114.9(12) . . ?
N3 C9 C10 119.6(14) . . ?
N3 C9 C8 115.5(12) . . ?
C10 C9 C8 124.7(14) . . ?
C9 C10 C11 120.9(15) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 118.4(15) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 116.9(17) . . ?
C13 C12 H12 121.6 . . ?
C11 C12 H12 121.6 . . ?
N3 C13 C12 124.4(16) . . ?
N3 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 N1 C2' -18(6) . . . . ?
N3 Cu1 N1 C2' -100(9) . . . . ?
N2 Cu1 N1 C2' 161(6) . . . . ?
O3 Cu1 N1 C2' 76(6) . . . . ?
O4 Cu1 N1 C2' -109(6) . . . . ?
O1 Cu1 N1 C2 12(4) . . . . ?
N3 Cu1 N1 C2 -71(9) . . . . ?
N2 Cu1 N1 C2 -170(4) . . . . ?
O3 Cu1 N1 C2 105(4) . . . . ?
O4 Cu1 N1 C2 -80(4) . . . . ?
O1 Cu1 N2 C4 161(6) . . . . ?
N3 Cu1 N2 C4 178.7(14) . . . . ?
N1 Cu1 N2 C4 -5.0(14) . . . . ?
O3 Cu1 N2 C4 88.8(13) . . . . ?
O4 Cu1 N2 C4 -99.3(13) . . . . ?
O1 Cu1 N2 C8 -11(7) . . . . ?
N3 Cu1 N2 C8 7.3(10) . . . . ?
N1 Cu1 N2 C8 -176.4(10) . . . . ?
O3 Cu1 N2 C8 -82.6(10) . . . . ?
O4 Cu1 N2 C8 89.3(10) . . . . ?
O1 Cu1 N3 C13 -8.3(13) . . . . ?
N1 Cu1 N3 C13 74(8) . . . . ?
N2 Cu1 N3 C13 173.2(13) . . . . ?
O3 Cu1 N3 C13 -102.0(13) . . . . ?
O4 Cu1 N3 C13 83.1(13) . . . . ?
O1 Cu1 N3 C9 172.5(11) . . . . ?
N1 Cu1 N3 C9 -105(7) . . . . ?
N2 Cu1 N3 C9 -6.0(11) . . . . ?
O3 Cu1 N3 C9 78.8(11) . . . . ?
O4 Cu1 N3 C9 -96.0(11) . . . . ?
N3 Cu1 O1 C1 -178.2(11) . . . . ?
N1 Cu1 O1 C1 5.5(12) . . . . ?
N2 Cu1 O1 C1 -160(6) . . . . ?
O3 Cu1 O1 C1 -88.8(11) . . . . ?
O4 Cu1 O1 C1 99.8(11) . . . . ?
O6 N4 O4 Cu1 -132.5(15) . . . . ?
O5 N4 O4 Cu1 50.2(18) . . . . ?
O1 Cu1 O4 N4 -112.2(12) . . . . ?
N3 Cu1 O4 N4 154.3(12) . . . . ?
N1 Cu1 O4 N4 -26.3(12) . . . . ?
N2 Cu1 O4 N4 72.5(12) . . . . ?
O3 Cu1 O4 N4 124.1(18) . . . . ?
Cu1 O1 C1 O2 176.3(13) . . . . ?
Cu1 O1 C1 C2' 9(6) . . . . ?
Cu1 O1 C1 C2 -22(4) . . . . ?
C2' N1 C2 C1 69(9) . . . . ?
Cu1 N1 C2 C1 -24(7) . . . . ?
C2' N1 C2 C3 -58(11) . . . . ?
Cu1 N1 C2 C3 -151(6) . . . . ?
O2 C1 C2 N1 -167(3) . . . . ?
O1 C1 C2 N1 31(7) . . . . ?
C2' C1 C2 N1 -69(9) . . . . ?
O2 C1 C2 C3 -43(10) . . . . ?
O1 C1 C2 C3 155(6) . . . . ?
C2' C1 C2 C3 55(11) . . . . ?
C2 N1 C2' C1 -70(10) . . . . ?
Cu1 N1 C2' C1 26(9) . . . . ?
C2 N1 C2' C3' 55(13) . . . . ?
Cu1 N1 C2' C3' 151(9) . . . . ?
O2 C1 C2' N1 168(5) . . . . ?
O1 C1 C2' N1 -24(11) . . . . ?
C2 C1 C2' N1 69(10) . . . . ?
O2 C1 C2' C3' 43(13) . . . . ?
O1 C1 C2' C3' -149(8) . . . . ?
C2 C1 C2' C3' -56(13) . . . . ?
C8 N2 C4 C5 -1(2) . . . . ?
Cu1 N2 C4 C5 -172.3(12) . . . . ?
N2 C4 C5 C6 4(3) . . . . ?
C4 C5 C6 C7 -3(3) . . . . ?
C5 C6 C7 C8 0(3) . . . . ?
C6 C7 C8 N2 2(2) . . . . ?
C6 C7 C8 C9 -179.7(15) . . . . ?
C4 N2 C8 C7 -1(2) . . . . ?
Cu1 N2 C8 C7 170.9(12) . . . . ?
C4 N2 C8 C9 -179.8(13) . . . . ?
Cu1 N2 C8 C9 -7.5(17) . . . . ?
C13 N3 C9 C10 0(2) . . . . ?
Cu1 N3 C9 C10 179.1(12) . . . . ?
C13 N3 C9 C8 -175.6(13) . . . . ?
Cu1 N3 C9 C8 3.6(17) . . . . ?
C7 C8 C9 N3 -175.6(15) . . . . ?
N2 C8 C9 N3 3(2) . . . . ?
C7 C8 C9 C10 9(3) . . . . ?
N2 C8 C9 C10 -172.6(15) . . . . ?
N3 C9 C10 C11 1(2) . . . . ?
C8 C9 C10 C11 176.2(15) . . . . ?
C9 C10 C11 C12 0(2) . . . . ?
C10 C11 C12 C13 -3(2) . . . . ?
C9 N3 C13 C12 -3(2) . . . . ?
Cu1 N3 C13 C12 178.3(12) . . . . ?
C11 C12 C13 N3 4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.141
####################################################################### 
# 
# 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_111018f
_database_code_depnum_ccdc_archive 'CCDC 996767'
_audit_update_record             
;
2014-04-11 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 Cu N5 O7'
_chemical_formula_weight         416.84

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   Pnma

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

_cell_length_a                   8.0946(6)
_cell_length_b                   16.0439(12)
_cell_length_c                   14.1781(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1841.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2656
_cell_measurement_theta_min      2.539
_cell_measurement_theta_max      24.731

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             852
_exptl_absorpt_coefficient_mu    1.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5839
_exptl_absorpt_correction_T_max  0.6942
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            8631
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1690
_reflns_number_gt                1202
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1212P)²+3.0103P] 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     SHELXL
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1690
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.2148
_refine_ls_wR_factor_gt          0.1775
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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 0.53499(12) 0.2500 0.45654(6) 0.0465(5) Uani 1 2 d S . .
N1 N 0.5261(6) 0.1693(3) 0.3496(3) 0.0451(11) Uani 1 1 d . . .
N2 N 0.7175(8) 0.1337(4) 0.5567(4) 0.0734(17) Uani 1 1 d . . .
N3 N 0.1559(13) 0.2232(7) 0.6320(7) 0.071(6) Uani 0.50 1 d P . .
O1 O 0.5719(6) 0.1626(3) 0.5540(3) 0.0633(12) Uani 1 1 d . . .
O2 O 0.8138(7) 0.1524(6) 0.4967(5) 0.143(3) Uani 1 1 d . . .
O3 O 0.7552(8) 0.0891(5) 0.6225(5) 0.127(2) Uani 1 1 d . . .
O4 O 0.2714(7) 0.2500 0.4958(4) 0.0541(14) Uani 1 2 d S . .
C1 C 0.5373(6) 0.2039(3) 0.2644(3) 0.0428(12) Uani 1 1 d . . .
C2 C 0.5438(8) 0.1556(4) 0.1832(4) 0.0633(17) Uani 1 1 d . . .
H2 H 0.5537 0.1806 0.1243 0.076 Uiso 1 1 calc R . .
C3 C 0.5357(9) 0.0719(5) 0.1911(5) 0.075(2) Uani 1 1 d . . .
H3 H 0.5416 0.0387 0.1374 0.091 Uiso 1 1 calc R . .
C4 C 0.5188(9) 0.0355(4) 0.2786(5) 0.074(2) Uani 1 1 d . . .
H4 H 0.5085 -0.0220 0.2850 0.089 Uiso 1 1 calc R . .
C5 C 0.5176(9) 0.0867(4) 0.3561(5) 0.0635(17) Uani 1 1 d . . .
H5 H 0.5105 0.0627 0.4157 0.076 Uiso 1 1 calc R . .
C6 C 0.2099(13) 0.2796(8) 0.5704(8) 0.057(4) Uani 0.50 1 d P . .
H6 H 0.2029 0.3366 0.5815 0.068 Uiso 0.50 1 d PR . .
C7 C 0.0675(16) 0.2500 0.7174(8) 0.112(5) Uani 1 2 d S . .
H7A H 0.1264 0.2312 0.7722 0.167 Uiso 0.50 1 d PR . .
H7B H -0.0416 0.2265 0.7174 0.167 Uiso 0.50 1 d PR . .
H7C H 0.0599 0.3097 0.7183 0.167 Uiso 0.50 1 d PR . .
C8 C 0.1807(13) 0.1343(7) 0.6060(8) 0.049(3) Uani 0.50 1 d P . .
H8A H 0.2591 0.1306 0.5554 0.074 Uiso 0.50 1 d PR . .
H8B H 0.0774 0.1107 0.5862 0.074 Uiso 0.50 1 d PR . .
H8C H 0.2215 0.1042 0.6596 0.074 Uiso 0.50 1 d PR . .


_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 1.992(4) 7_565 ?
Cu1 O1 1.992(4) . ?
Cu1 N1 1.995(4) . ?
Cu1 N1 1.995(4) 7_565 ?
Cu1 O4 2.205(5) . ?
N1 C5 1.330(8) . ?
N1 C1 1.333(7) . ?
N2 O2 1.192(8) . ?
N2 O3 1.214(7) . ?
N2 O1 1.267(7) . ?
N3 N3 0.86(2) 7_565 ?
N3 C6 0.978(13) 7_565 ?
N3 C6 1.331(14) . ?
N3 C7 1.471(14) . ?
N3 C8 1.487(16) . ?
O4 C6 1.261(12) 7_565 ?
O4 C6 1.261(12) . ?
C1 C2 1.389(8) . ?
C1 C1 1.478(11) 7_565 ?
C2 C3 1.350(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(9) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C6 0.95(3) 7_565 ?
C6 N3 0.978(13) 7_565 ?
C6 C8 1.490(15) 7_565 ?
C6 H6 0.9300 . ?
C7 N3 1.471(14) 7_565 ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C6 1.490(15) 7_565 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 89.5(3) 7_565 . ?
O1 Cu1 N1 171.82(18) 7_565 . ?
O1 Cu1 N1 94.3(2) . . ?
O1 Cu1 N1 94.3(2) 7_565 7_565 ?
O1 Cu1 N1 171.82(18) . 7_565 ?
N1 Cu1 N1 80.9(3) . 7_565 ?
O1 Cu1 O4 88.29(16) 7_565 . ?
O1 Cu1 O4 88.29(16) . . ?
N1 Cu1 O4 99.02(17) . . ?
N1 Cu1 O4 99.02(17) 7_565 . ?
C5 N1 C1 118.8(5) . . ?
C5 N1 Cu1 126.6(4) . . ?
C1 N1 Cu1 114.6(4) . . ?
O2 N2 O3 122.2(7) . . ?
O2 N2 O1 119.7(6) . . ?
O3 N2 O1 118.1(6) . . ?
N3 N3 C6 92.6(11) 7_565 7_565 ?
N3 N3 C6 47.2(7) 7_565 . ?
C6 N3 C6 45.4(13) 7_565 . ?
N3 N3 C7 73.0(5) 7_565 . ?
C6 N3 C7 165.1(14) 7_565 . ?
C6 N3 C7 120.2(9) . . ?
N3 N3 C8 163.6(6) 7_565 . ?
C6 N3 C8 71.0(11) 7_565 . ?
C6 N3 C8 116.4(9) . . ?
C7 N3 C8 123.3(8) . . ?
N2 O1 Cu1 114.7(4) . . ?
C6 O4 C6 44.2(12) 7_565 . ?
C6 O4 Cu1 126.4(6) 7_565 . ?
C6 O4 Cu1 126.4(6) . . ?
N1 C1 C2 121.4(5) . . ?
N1 C1 C1 114.6(3) . 7_565 ?
C2 C1 C1 123.9(3) . 7_565 ?
C3 C2 C1 119.0(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.1(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 117.9(6) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 122.8(6) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C6 C6 N3 87.4(11) 7_565 7_565 ?
C6 C6 O4 67.9(6) 7_565 . ?
N3 C6 O4 155.2(15) 7_565 . ?
C6 C6 N3 47.2(7) 7_565 . ?
N3 C6 N3 40.1(12) 7_565 . ?
O4 C6 N3 115.1(10) . . ?
C6 C6 C8 158.0(7) 7_565 7_565 ?
N3 C6 C8 70.7(11) 7_565 7_565 ?
O4 C6 C8 134.1(12) . 7_565 ?
N3 C6 C8 110.8(10) . 7_565 ?
C6 C6 H6 169.6 7_565 . ?
N3 C6 H6 82.3 7_565 . ?
O4 C6 H6 122.4 . . ?
N3 C6 H6 122.4 . . ?
C8 C6 H6 11.7 7_565 . ?
N3 C7 N3 33.9(9) . 7_565 ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7A 121.1 7_565 . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7B 124.2 7_565 . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
N3 C7 H7C 75.6 7_565 . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C6 38.4(6) . 7_565 ?
N3 C8 H8A 109.5 . . ?
C6 C8 H8A 72.5 7_565 . ?
N3 C8 H8B 109.5 . . ?
C6 C8 H8B 113.9 7_565 . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
C6 C8 H8C 132.9 7_565 . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 N1 C5 128.6(13) 7_565 . . . ?
O1 Cu1 N1 C5 10.7(6) . . . . ?
N1 Cu1 N1 C5 -176.1(5) 7_565 . . . ?
O4 Cu1 N1 C5 -78.3(5) . . . . ?
O1 Cu1 N1 C1 -48.3(15) 7_565 . . . ?
O1 Cu1 N1 C1 -166.2(4) . . . . ?
N1 Cu1 N1 C1 7.0(5) 7_565 . . . ?
O4 Cu1 N1 C1 104.8(4) . . . . ?
O2 N2 O1 Cu1 -8.3(10) . . . . ?
O3 N2 O1 Cu1 169.8(6) . . . . ?
O1 Cu1 O1 N2 -96.4(5) 7_565 . . . ?
N1 Cu1 O1 N2 76.4(5) . . . . ?
N1 Cu1 O1 N2 21.8(16) 7_565 . . . ?
O4 Cu1 O1 N2 175.3(5) . . . . ?
O1 Cu1 O4 C6 -72.6(7) 7_565 . . 7_565 ?
O1 Cu1 O4 C6 16.9(7) . . . 7_565 ?
N1 Cu1 O4 C6 111.1(8) . . . 7_565 ?
N1 Cu1 O4 C6 -166.8(7) 7_565 . . 7_565 ?
O1 Cu1 O4 C6 -16.9(7) 7_565 . . . ?
O1 Cu1 O4 C6 72.6(7) . . . . ?
N1 Cu1 O4 C6 166.8(7) . . . . ?
N1 Cu1 O4 C6 -111.1(7) 7_565 . . . ?
C5 N1 C1 C2 -1.4(8) . . . . ?
Cu1 N1 C1 C2 175.7(5) . . . . ?
C5 N1 C1 C1 177.0(4) . . . 7_565 ?
Cu1 N1 C1 C1 -5.9(4) . . . 7_565 ?
N1 C1 C2 C3 1.2(10) . . . . ?
C1 C1 C2 C3 -177.1(5) 7_565 . . . ?
C1 C2 C3 C4 0.9(11) . . . . ?
C2 C3 C4 C5 -2.7(12) . . . . ?
C1 N1 C5 C4 -0.4(10) . . . . ?
Cu1 N1 C5 C4 -177.2(5) . . . . ?
C3 C4 C5 N1 2.4(11) . . . . ?
Cu1 O4 C6 C6 -107.4(6) . . . 7_565 ?
C6 O4 C6 N3 -3(3) 7_565 . . 7_565 ?
Cu1 O4 C6 N3 -111(3) . . . 7_565 ?
C6 O4 C6 N3 -1.1(11) 7_565 . . . ?
Cu1 O4 C6 N3 -108.5(9) . . . . ?
C6 O4 C6 C8 180.0(10) 7_565 . . 7_565 ?
Cu1 O4 C6 C8 72.6(14) . . . 7_565 ?
N3 N3 C6 C6 180.000(7) 7_565 . . 7_565 ?
C7 N3 C6 C6 -175.6(14) . . . 7_565 ?
C8 N3 C6 C6 0.6(6) . . . 7_565 ?
C6 N3 C6 N3 180.000(2) 7_565 . . 7_565 ?
C7 N3 C6 N3 4.4(15) . . . 7_565 ?
C8 N3 C6 N3 -179.4(6) . . . 7_565 ?
N3 N3 C6 O4 -178.6(14) 7_565 . . . ?
C6 N3 C6 O4 1.4(14) 7_565 . . . ?
C7 N3 C6 O4 -174.2(9) . . . . ?
C8 N3 C6 O4 2.1(14) . . . . ?
N3 N3 C6 C8 0.6(5) 7_565 . . 7_565 ?
C6 N3 C6 C8 -179.4(5) 7_565 . . 7_565 ?
C7 N3 C6 C8 5.0(15) . . . 7_565 ?
C8 N3 C6 C8 -178.8(11) . . . 7_565 ?
C6 N3 C7 N3 -16(5) 7_565 . . 7_565 ?
C6 N3 C7 N3 -3.4(11) . . . 7_565 ?
C8 N3 C7 N3 -179.3(8) . . . 7_565 ?
N3 N3 C8 C6 -2.1(19) 7_565 . . 7_565 ?
C6 N3 C8 C6 -0.5(4) . . . 7_565 ?
C7 N3 C8 C6 175.6(15) . . . 7_565 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.075
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.101
####################################################################### 
# 
# 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_AA
_database_code_depnum_ccdc_archive 'CCDC 996768'
_audit_update_record             
;
2014-04-11 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_formula_moiety         'C13 H15 Cu N5 O7'
_chemical_formula_sum            'C13 H15 Cu N5 O7'
_chemical_formula_weight         416.84
_chemical_melting_point          ?
_chemical_name_common            ?
_chemical_name_systematic        ?
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'
Cu Cu 0.3201 1.2651 '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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_angle_alpha                75.219(3)
_cell_angle_beta                 76.986(3)
_cell_angle_gamma                86.001(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3639(5)
_cell_length_b                   9.9381(5)
_cell_length_c                   11.0317(6)
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_cell_volume                     863.78(8)
_exptl_absorpt_coefficient_mu    1.312
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_F_000             426
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           ?
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11947
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2818
_reflns_number_total             4035
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
;
A short history of SHELX (Sheldrick, 2007)/Bruker
;
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.051
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0429
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1260
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.0664P)²+0.1404P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
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 0.72532(4) 0.68588(3) 0.72351(3) 0.06124(16) Uani 1 1 d . . .
O1 O 0.4930(2) 0.6840(2) 0.7990(2) 0.0740(6) Uani 1 1 d . A .
N2 N 0.7337(3) 0.4781(2) 0.7443(2) 0.0586(6) Uani 1 1 d . A .
N1 N 0.9622(3) 0.6641(3) 0.6531(2) 0.0596(6) Uani 1 1 d . A .
N3 N 0.2571(3) 0.7842(3) 0.8747(2) 0.0679(6) Uani 1 1 d . A .
C5 C 1.0158(3) 0.5321(3) 0.6591(3) 0.0592(7) Uani 1 1 d . . .
C12 C 0.4100(4) 0.7902(4) 0.8131(3) 0.0666(7) Uani 1 1 d . . .
C6 C 0.8856(4) 0.4267(3) 0.7074(2) 0.0590(7) Uani 1 1 d . A .
O4 O 0.6640(8) 0.7419(5) 0.4968(11) 0.103(2) Uani 0.84(2) 1 d P A 1
N5 N 0.6888(4) 0.8603(4) 0.4883(4) 0.0938(11) Uani 1 1 d . . .
C1 C 1.0706(4) 0.7679(4) 0.6077(3) 0.0714(8) Uani 1 1 d . . .
H1 H 1.0330 0.8588 0.6042 0.086 Uiso 1 1 calc R A .
C10 C 0.6075(4) 0.3909(3) 0.7891(3) 0.0747(8) Uani 1 1 d . . .
H10 H 0.5027 0.4259 0.8147 0.090 Uiso 1 1 calc R A .
C7 C 0.9136(5) 0.2875(3) 0.7149(3) 0.0778(9) Uani 1 1 d . . .
H7 H 1.0190 0.2538 0.6891 0.093 Uiso 1 1 calc R A .
N4 N 0.7499(4) 0.7809(5) 0.9449(4) 0.1006(13) Uani 1 1 d . . .
C2 C 1.2350(4) 0.7444(4) 0.5664(3) 0.0811(9) Uani 1 1 d . A .
H2 H 1.3073 0.8184 0.5330 0.097 Uiso 1 1 calc R . .
C4 C 1.1813(4) 0.5031(4) 0.6216(3) 0.0790(9) Uani 1 1 d . A .
H4 H 1.2183 0.4116 0.6277 0.095 Uiso 1 1 calc R . .
O2 O 0.7204(4) 0.8865(3) 0.5919(4) 0.0959(11) Uani 0.845(5) 1 d P A 1
O10 O 0.7644(5) 0.8407(4) 0.8180(4) 0.0939(11) Uani 0.703(4) 1 d P A 1
C11 C 0.1745(4) 0.6517(4) 0.9313(3) 0.0832(10) Uani 1 1 d . . .
H11A H 0.1092 0.6352 0.8753 0.125 Uiso 1 1 calc R A .
H11C H 0.1049 0.6540 1.0129 0.125 Uiso 1 1 calc R . .
H11B H 0.2547 0.5783 0.9431 0.125 Uiso 1 1 calc R . .
C3 C 1.2904(4) 0.6113(5) 0.5752(4) 0.0852(10) Uani 1 1 d . . .
H3 H 1.4019 0.5933 0.5498 0.102 Uiso 1 1 calc R A .
C9 C 0.6291(5) 0.2504(4) 0.7984(4) 0.0904(11) Uani 1 1 d . A .
H9 H 0.5399 0.1911 0.8296 0.109 Uiso 1 1 calc R . .
C8 C 0.7830(6) 0.1990(4) 0.7612(4) 0.0938(11) Uani 1 1 d . A .
H8 H 0.7993 0.1042 0.7672 0.113 Uiso 1 1 calc R . .
C13 C 0.1617(5) 0.9103(4) 0.8878(4) 0.0991(12) Uani 1 1 d . . .
H13A H 0.0748 0.9198 0.8422 0.149 Uiso 1 1 calc R A .
H13B H 0.2318 0.9896 0.8529 0.149 Uiso 1 1 calc R . .
H13C H 0.1159 0.9043 0.9770 0.149 Uiso 1 1 calc R . .
O8 O 0.7518(7) 0.6590(6) 0.9598(7) 0.1177(18) Uani 0.738(10) 1 d P A 1
O9 O 0.7547(11) 0.8682(11) 0.9992(8) 0.134(2) Uani 0.491(6) 1 d P A 1
O3 O 0.6856(11) 0.9574(8) 0.3988(6) 0.204(4) Uani 0.771(11) 1 d P A 1
H12 H 0.454(4) 0.888(4) 0.777(3) 0.078(9) Uiso 1 1 d . . .
O7 O 0.7762(10) 0.7477(10) 1.0702(8) 0.134(2) Uani 0.509(6) 1 d P A 2
O5 O 0.803(2) 0.7082(17) 0.891(2) 0.1177(18) Uani 0.262(10) 1 d P A 2
O6 O 0.6677(12) 0.8822(10) 0.9397(10) 0.0939(11) Uani 0.297(4) 1 d P A 2
O11 O 0.633(4) 0.748(3) 0.557(5) 0.103(2) Uani 0.16(2) 1 d P A 2
O12 O 0.648(4) 0.866(3) 0.379(2) 0.204(4) Uani 0.229(11) 1 d P A 2
O13 O 0.798(2) 0.9135(18) 0.463(2) 0.0959(11) Uani 0.155(5) 1 d P A 2


_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 1.933(2) . ?
Cu1 N2 2.016(2) . ?
Cu1 N1 1.977(2) . ?
Cu1 O2 2.150(3) . ?
Cu1 O10 2.145(4) . ?
Cu1 O5 2.158(19) . ?
Cu1 O11 2.08(4) . ?
O1 C12 1.246(4) . ?
N2 C6 1.350(4) . ?
N2 C10 1.336(4) . ?
N1 C5 1.347(4) . ?
N1 C1 1.341(4) . ?
N3 C12 1.304(4) . ?
N3 C11 1.455(4) . ?
N3 C13 1.458(4) . ?
C5 C6 1.477(4) . ?
C5 C4 1.384(4) . ?
C6 C7 1.371(4) . ?
O4 N5 1.186(6) . ?
N5 O2 1.319(5) . ?
N5 O3 1.195(6) . ?
N5 O11 1.23(3) . ?
N5 O12 1.32(3) . ?
N5 O13 1.03(2) . ?
C1 C2 1.371(4) . ?
C10 C9 1.375(5) . ?
C7 C8 1.371(5) . ?
N4 O10 1.356(6) . ?
N4 O8 1.179(7) . ?
N4 O9 1.181(8) . ?
N4 O7 1.401(9) . ?
N4 O5 1.06(2) . ?
N4 O6 1.175(10) . ?
C2 C3 1.357(5) . ?
C4 C3 1.378(5) . ?
C9 C8 1.365(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 N2 92.29(9) . . ?
O1 Cu1 N1 173.40(9) . . ?
O1 Cu1 O2 95.22(11) . . ?
O1 Cu1 O10 91.07(12) . . ?
O1 Cu1 O5 95.6(5) . . ?
O1 Cu1 O11 80.3(11) . . ?
O1 C12 N3 122.3(3) . . ?
N2 Cu1 O2 145.67(13) . . ?
N2 Cu1 O10 141.38(13) . . ?
N2 Cu1 O5 103.0(4) . . ?
N2 Cu1 O11 99.7(9) . . ?
N2 C6 C5 114.5(2) . . ?
N2 C6 C7 121.8(3) . . ?
N2 C10 C9 121.5(3) . . ?
N1 Cu1 N2 81.23(10) . . ?
N1 Cu1 O2 90.85(11) . . ?
N1 Cu1 O10 93.27(12) . . ?
N1 Cu1 O5 84.8(5) . . ?
N1 Cu1 O11 101.9(11) . . ?
N1 C5 C6 114.6(2) . . ?
N1 C5 C4 120.6(3) . . ?
N1 C1 C2 122.2(3) . . ?
C5 N1 Cu1 115.36(19) . . ?
C12 O1 Cu1 123.9(2) . . ?
C12 N3 C11 121.2(3) . . ?
C12 N3 C13 121.3(3) . . ?
C6 N2 Cu1 114.08(19) . . ?
C6 C7 C8 118.7(3) . . ?
O4 N5 O2 115.1(6) . . ?
O4 N5 O3 127.8(9) . . ?
O4 N5 O11 32.3(17) . . ?
O4 N5 O12 77.7(14) . . ?
N5 O2 Cu1 104.9(2) . . ?
N5 O11 Cu1 112(2) . . ?
C1 N1 Cu1 125.3(2) . . ?
C1 N1 C5 119.2(3) . . ?
C10 N2 Cu1 127.0(2) . . ?
C10 N2 C6 119.0(3) . . ?
C7 C6 C5 123.7(3) . . ?
N4 O10 Cu1 109.0(3) . . ?
N4 O5 Cu1 123.8(12) . . ?
C2 C3 C4 119.9(3) . . ?
C4 C5 C6 124.8(3) . . ?
O2 Cu1 O5 109.5(4) . . ?
O10 Cu1 O2 72.00(15) . . ?
O10 Cu1 O5 38.4(4) . . ?
O10 N4 O7 161.7(5) . . ?
C11 N3 C13 117.5(3) . . ?
C3 C2 C1 118.8(3) . . ?
C3 C4 C5 119.2(3) . . ?
C9 C8 C7 119.8(3) . . ?
C8 C9 C10 119.3(3) . . ?
O8 N4 O10 108.3(5) . . ?
O8 N4 O9 142.1(8) . . ?
O8 N4 O7 83.6(6) . . ?
O9 N4 O10 109.1(7) . . ?
O9 N4 O7 58.6(5) . . ?
O3 N5 O2 117.1(6) . . ?
O3 N5 O11 149.9(18) . . ?
O3 N5 O12 50.3(10) . . ?
O5 N4 O10 70.5(11) . . ?
O5 N4 O8 43.2(9) . . ?
O5 N4 O9 154.1(10) . . ?
O5 N4 O7 114.0(12) . . ?
O5 N4 O6 142.4(13) . . ?
O6 N4 O10 74.6(7) . . ?
O6 N4 O8 145.8(6) . . ?
O6 N4 O9 53.7(7) . . ?
O6 N4 O7 103.6(7) . . ?
O11 Cu1 O2 49.2(8) . . ?
O11 Cu1 O10 118.8(9) . . ?
O11 Cu1 O5 157.1(10) . . ?
O11 N5 O2 87(2) . . ?
O11 N5 O12 103(2) . . ?
O12 N5 O2 166.4(13) . . ?
O13 N5 O4 130.3(11) . . ?
O13 N5 O2 71.1(13) . . ?
O13 N5 O3 70.3(12) . . ?
O13 N5 O11 138.2(19) . . ?
O13 N5 O12 104.8(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C12 N3 -173.7(2) . . . . ?
Cu1 N2 C6 C5 0.0(3) . . . . ?
Cu1 N2 C6 C7 -179.9(2) . . . . ?
Cu1 N2 C10 C9 179.8(3) . . . . ?
Cu1 N1 C5 C6 5.0(3) . . . . ?
Cu1 N1 C5 C4 -175.2(2) . . . . ?
Cu1 N1 C1 C2 176.5(2) . . . . ?
O1 Cu1 N2 C6 -176.75(19) . . . . ?
O1 Cu1 N2 C10 3.4(3) . . . . ?
O1 Cu1 N1 C5 6.6(9) . . . . ?
O1 Cu1 N1 C1 -169.6(7) . . . . ?
O1 Cu1 O2 N5 -88.5(2) . . . . ?
O1 Cu1 O10 N4 72.6(3) . . . . ?
O1 Cu1 O5 N4 -46.7(16) . . . . ?
O1 Cu1 O11 N5 124(3) . . . . ?
N2 Cu1 O1 C12 -179.5(3) . . . . ?
N2 Cu1 N1 C5 -3.92(19) . . . . ?
N2 Cu1 N1 C1 179.8(3) . . . . ?
N2 Cu1 O2 N5 13.3(3) . . . . ?
N2 Cu1 O10 N4 -22.4(4) . . . . ?
N2 Cu1 O5 N4 -140.4(15) . . . . ?
N2 Cu1 O11 N5 -146(2) . . . . ?
N2 C6 C7 C8 0.0(5) . . . . ?
N2 C10 C9 C8 0.1(6) . . . . ?
N1 Cu1 O1 C12 170.0(7) . . . . ?
N1 Cu1 N2 C6 2.05(19) . . . . ?
N1 Cu1 N2 C10 -177.8(3) . . . . ?
N1 Cu1 O2 N5 88.9(2) . . . . ?
N1 Cu1 O10 N4 -102.4(3) . . . . ?
N1 Cu1 O5 N4 139.9(16) . . . . ?
N1 Cu1 O11 N5 -63(3) . . . . ?
N1 C5 C6 N2 -3.2(4) . . . . ?
N1 C5 C6 C7 176.6(3) . . . . ?
N1 C5 C4 C3 -1.4(5) . . . . ?
N1 C1 C2 C3 -1.9(5) . . . . ?
C5 N1 C1 C2 0.4(5) . . . . ?
C5 C6 C7 C8 -179.9(3) . . . . ?
C5 C4 C3 C2 -0.2(5) . . . . ?
C6 N2 C10 C9 0.0(5) . . . . ?
C6 C5 C4 C3 178.4(3) . . . . ?
C6 C7 C8 C9 0.1(6) . . . . ?
O4 N5 O2 Cu1 3.8(5) . . . . ?
O4 N5 O11 Cu1 127(4) . . . . ?
C1 N1 C5 C6 -178.5(3) . . . . ?
C1 N1 C5 C4 1.3(4) . . . . ?
C1 C2 C3 C4 1.8(6) . . . . ?
C10 N2 C6 C5 179.8(2) . . . . ?
C10 N2 C6 C7 0.0(4) . . . . ?
C10 C9 C8 C7 -0.2(6) . . . . ?
C4 C5 C6 N2 176.9(3) . . . . ?
C4 C5 C6 C7 -3.2(5) . . . . ?
O2 Cu1 O1 C12 -33.1(3) . . . . ?
O2 Cu1 N2 C6 80.6(3) . . . . ?
O2 Cu1 N2 C10 -99.3(3) . . . . ?
O2 Cu1 N1 C5 -150.4(2) . . . . ?
O2 Cu1 N1 C1 33.4(3) . . . . ?
O2 Cu1 O10 N4 167.7(3) . . . . ?
O2 Cu1 O5 N4 50.9(17) . . . . ?
O2 Cu1 O11 N5 18.1(16) . . . . ?
O2 N5 O11 Cu1 -22.6(19) . . . . ?
O10 Cu1 O1 C12 38.9(3) . . . . ?
O10 Cu1 N2 C6 -82.2(3) . . . . ?
O10 Cu1 N2 C10 98.0(3) . . . . ?
O10 Cu1 N1 C5 137.6(2) . . . . ?
O10 Cu1 N1 C1 -38.6(3) . . . . ?
O10 Cu1 O2 N5 -178.0(3) . . . . ?
O10 Cu1 O5 N4 38.0(11) . . . . ?
O10 Cu1 O11 N5 38(3) . . . . ?
O10 N4 O5 Cu1 -39.9(11) . . . . ?
C11 N3 C12 O1 0.2(5) . . . . ?
C13 N3 C12 O1 -178.9(3) . . . . ?
O8 N4 O10 Cu1 13.3(4) . . . . ?
O8 N4 O5 Cu1 109.9(18) . . . . ?
O9 N4 O10 Cu1 -172.9(5) . . . . ?
O9 N4 O5 Cu1 -134(2) . . . . ?
O3 N5 O2 Cu1 -177.5(5) . . . . ?
O3 N5 O11 Cu1 -168.5(19) . . . . ?
O7 N4 O10 Cu1 142.0(16) . . . . ?
O7 N4 O5 Cu1 159.3(9) . . . . ?
O5 Cu1 O1 C12 77.1(5) . . . . ?
O5 Cu1 N2 C6 -80.5(6) . . . . ?
O5 Cu1 N2 C10 99.7(6) . . . . ?
O5 Cu1 N1 C5 100.1(5) . . . . ?
O5 Cu1 N1 C1 -76.1(5) . . . . ?
O5 Cu1 O2 N5 173.6(6) . . . . ?
O5 Cu1 O10 N4 -25.0(8) . . . . ?
O5 Cu1 O11 N5 42(5) . . . . ?
O5 N4 O10 Cu1 34.6(9) . . . . ?
O6 N4 O10 Cu1 -131.1(6) . . . . ?
O6 N4 O5 Cu1 -17(3) . . . . ?
O11 Cu1 O1 C12 -80.1(9) . . . . ?
O11 Cu1 N2 C6 102.7(11) . . . . ?
O11 Cu1 N2 C10 -77.1(11) . . . . ?
O11 Cu1 N1 C5 -102.0(9) . . . . ?
O11 Cu1 N1 C1 81.7(9) . . . . ?
O11 Cu1 O2 N5 -16.2(15) . . . . ?
O11 Cu1 O10 N4 152.1(12) . . . . ?
O11 Cu1 O5 N4 32(4) . . . . ?
O11 N5 O2 Cu1 20.9(16) . . . . ?
O12 N5 O2 Cu1 163(6) . . . . ?
O12 N5 O11 Cu1 166(2) . . . . ?
O13 N5 O2 Cu1 -122.7(11) . . . . ?
O13 N5 O11 Cu1 35(5) . . . . ?
####################################################################### 
# 
# 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_090611b_0m
_database_code_depnum_ccdc_archive 'CCDC 996769'
_audit_update_record             
;
2014-04-11 deposited with the CCDC.
2015-11-11 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 H15 Cu N3 O5'
_chemical_formula_weight         380.84

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   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                   8.8890(2)
_cell_length_b                   11.9445(3)
_cell_length_c                   15.1962(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.838(2)
_cell_angle_gamma                90.00
_cell_volume                     1589.73(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6327
_cell_measurement_theta_min      2.884
_cell_measurement_theta_max      27.837

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5402
_exptl_absorpt_correction_T_max  0.7664
_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            17798
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2811
_reflns_number_gt                2534
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0407P)²+0.6269P] 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     SHELXL
_refine_ls_extinction_coef       0.0072(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2811
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.61763(3) 0.329255(19) 0.107007(16) 0.03938(12) Uani 1 1 d . . .
O3 O 0.77041(18) 0.32676(12) 0.24969(10) 0.0515(4) Uani 1 1 d . . .
N2 N 0.41297(19) 0.31929(13) 0.14448(11) 0.0389(4) Uani 1 1 d . . .
O5 O 0.62998(17) 0.17057(12) 0.09652(11) 0.0509(4) Uani 1 1 d . . .
O4 O 0.78537(17) 0.35778(12) 0.04579(10) 0.0471(3) Uani 1 1 d . . .
N1 N 0.5712(2) 0.49214(14) 0.11290(11) 0.0402(4) Uani 1 1 d . . .
C7 C 0.2166(2) 0.4237(2) 0.19548(15) 0.0520(5) Uani 1 1 d . . .
H7 H 0.1786 0.4920 0.2113 0.062 Uiso 1 1 calc R . .
C8 C 0.1362(3) 0.3260(2) 0.20248(17) 0.0572(6) Uani 1 1 d . . .
H8 H 0.0428 0.3282 0.2222 0.069 Uiso 1 1 calc R . .
C6 C 0.3540(2) 0.41856(17) 0.16472(13) 0.0401(4) Uani 1 1 d . . .
N3 N 0.7826(2) 0.41439(15) 0.29698(12) 0.0460(4) Uani 1 1 d . . .
C13 C 0.8391(3) 0.16854(18) 0.01957(15) 0.0500(5) Uani 1 1 d . . .
H13 H 0.9045 0.1218 -0.0051 0.060 Uiso 1 1 calc R . .
C12 C 0.8612(2) 0.28236(19) 0.01337(13) 0.0439(5) Uani 1 1 d . . .
O1 O 0.9099(2) 0.45497(18) 0.32234(15) 0.0824(6) Uani 1 1 d . . .
C10 C 0.3349(2) 0.22527(19) 0.15242(14) 0.0450(5) Uani 1 1 d . . .
H10 H 0.3763 0.1573 0.1387 0.054 Uiso 1 1 calc R . .
O2 O 0.66802(19) 0.45667(14) 0.31904(11) 0.0591(4) Uani 1 1 d . . .
C5 C 0.4455(2) 0.51721(17) 0.14721(12) 0.0395(4) Uani 1 1 d . . .
C4 C 0.4064(2) 0.62705(18) 0.16203(14) 0.0478(5) Uani 1 1 d . . .
H4 H 0.3218 0.6431 0.1883 0.057 Uiso 1 1 calc R . .
C11 C 0.9832(3) 0.3238(2) -0.03573(17) 0.0604(6) Uani 1 1 d . . .
H11C H 1.0803 0.3214 0.0032 0.091 Uiso 1 1 calc R . .
H11B H 0.9609 0.3995 -0.0550 0.091 Uiso 1 1 calc R . .
H11A H 0.9864 0.2771 -0.0868 0.091 Uiso 1 1 calc R . .
C1 C 0.6574(3) 0.57593(18) 0.08998(15) 0.0491(5) Uani 1 1 d . . .
H1 H 0.7445 0.5587 0.0664 0.059 Uiso 1 1 calc R . .
C14 C 0.7268(2) 0.11776(17) 0.05972(14) 0.0433(5) Uani 1 1 d . . .
C3 C 0.4949(3) 0.71220(19) 0.13718(15) 0.0531(6) Uani 1 1 d . . .
H3 H 0.4695 0.7865 0.1454 0.064 Uiso 1 1 calc R . .
C2 C 0.6210(3) 0.68638(19) 0.10017(15) 0.0539(6) Uani 1 1 d . . .
H2 H 0.6811 0.7429 0.0822 0.065 Uiso 1 1 calc R . .
C9 C 0.1949(2) 0.2255(2) 0.18019(15) 0.0529(6) Uani 1 1 d . . .
H9 H 0.1416 0.1592 0.1837 0.063 Uiso 1 1 calc R . .
C15 C 0.7148(3) -0.00722(19) 0.05939(18) 0.0603(6) Uani 1 1 d . . .
H15C H 0.8096 -0.0388 0.0887 0.090 Uiso 1 1 calc R . .
H15B H 0.6928 -0.0336 -0.0011 0.090 Uiso 1 1 calc R . .
H15A H 0.6342 -0.0295 0.0904 0.090 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 O5 1.9068(14) . ?
Cu1 O4 1.9180(14) . ?
Cu1 N1 1.9940(17) . ?
Cu1 N2 2.0005(17) . ?
Cu1 O3 2.3538(16) . ?
O3 N3 1.264(2) . ?
N2 C10 1.337(3) . ?
N2 C6 1.353(3) . ?
O5 C14 1.271(3) . ?
O4 C12 1.274(3) . ?
N1 C1 1.342(3) . ?
N1 C5 1.345(3) . ?
C7 C8 1.382(3) . ?
C7 C6 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(3) . ?
C8 H8 0.9300 . ?
C6 C5 1.481(3) . ?
N3 O1 1.231(2) . ?
N3 O2 1.233(2) . ?
C13 C12 1.379(3) . ?
C13 C14 1.395(3) . ?
C13 H13 0.9300 . ?
C12 C11 1.502(3) . ?
C10 C9 1.380(3) . ?
C10 H10 0.9300 . ?
C5 C4 1.385(3) . ?
C4 C3 1.377(3) . ?
C4 H4 0.9300 . ?
C11 H11C 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11A 0.9600 . ?
C1 C2 1.373(3) . ?
C1 H1 0.9300 . ?
C14 C15 1.497(3) . ?
C3 C2 1.372(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C15 H15C 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15A 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Cu1 O4 94.32(6) . . ?
O5 Cu1 N1 171.46(7) . . ?
O4 Cu1 N1 91.86(7) . . ?
O5 Cu1 N2 91.88(7) . . ?
O4 Cu1 N2 165.64(7) . . ?
N1 Cu1 N2 80.79(7) . . ?
O5 Cu1 O3 91.84(6) . . ?
O4 Cu1 O3 94.30(6) . . ?
N1 Cu1 O3 93.57(6) . . ?
N2 Cu1 O3 98.43(6) . . ?
N3 O3 Cu1 119.56(12) . . ?
C10 N2 C6 119.25(18) . . ?
C10 N2 Cu1 125.97(15) . . ?
C6 N2 Cu1 114.77(13) . . ?
C14 O5 Cu1 125.67(14) . . ?
C12 O4 Cu1 124.66(14) . . ?
C1 N1 C5 118.92(18) . . ?
C1 N1 Cu1 125.75(15) . . ?
C5 N1 Cu1 115.25(14) . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
N2 C6 C7 121.0(2) . . ?
N2 C6 C5 114.25(17) . . ?
C7 C6 C5 124.71(19) . . ?
O1 N3 O2 120.8(2) . . ?
O1 N3 O3 119.28(19) . . ?
O2 N3 O3 119.93(18) . . ?
C12 C13 C14 125.4(2) . . ?
C12 C13 H13 117.3 . . ?
C14 C13 H13 117.3 . . ?
O4 C12 C13 125.4(2) . . ?
O4 C12 C11 115.7(2) . . ?
C13 C12 C11 118.9(2) . . ?
N2 C10 C9 122.3(2) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
N1 C5 C4 121.44(19) . . ?
N1 C5 C6 114.22(17) . . ?
C4 C5 C6 124.32(19) . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C12 C11 H11C 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
C12 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
N1 C1 C2 122.1(2) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
O5 C14 C13 124.4(2) . . ?
O5 C14 C15 116.3(2) . . ?
C13 C14 C15 119.2(2) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C8 C9 C10 118.5(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C14 C15 H15C 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
H15B C15 H15A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 Cu1 O3 N3 -169.34(15) . . . . ?
O4 Cu1 O3 N3 96.18(15) . . . . ?
N1 Cu1 O3 N3 4.04(15) . . . . ?
N2 Cu1 O3 N3 -77.17(15) . . . . ?
O5 Cu1 N2 C10 -1.23(18) . . . . ?
O4 Cu1 N2 C10 114.4(3) . . . . ?
N1 Cu1 N2 C10 174.36(18) . . . . ?
O3 Cu1 N2 C10 -93.36(17) . . . . ?
O5 Cu1 N2 C6 177.35(14) . . . . ?
O4 Cu1 N2 C6 -67.0(3) . . . . ?
N1 Cu1 N2 C6 -7.06(14) . . . . ?
O3 Cu1 N2 C6 85.22(14) . . . . ?
O4 Cu1 O5 C14 0.73(18) . . . . ?
N1 Cu1 O5 C14 137.0(4) . . . . ?
N2 Cu1 O5 C14 167.78(17) . . . . ?
O3 Cu1 O5 C14 -93.72(17) . . . . ?
O5 Cu1 O4 C12 0.94(17) . . . . ?
N1 Cu1 O4 C12 -173.17(16) . . . . ?
N2 Cu1 O4 C12 -114.4(3) . . . . ?
O3 Cu1 O4 C12 93.11(16) . . . . ?
O5 Cu1 N1 C1 -144.6(4) . . . . ?
O4 Cu1 N1 C1 -8.18(18) . . . . ?
N2 Cu1 N1 C1 -175.77(18) . . . . ?
O3 Cu1 N1 C1 86.25(18) . . . . ?
O5 Cu1 N1 C5 38.8(5) . . . . ?
O4 Cu1 N1 C5 175.18(14) . . . . ?
N2 Cu1 N1 C5 7.59(14) . . . . ?
O3 Cu1 N1 C5 -90.39(14) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C10 N2 C6 C7 1.6(3) . . . . ?
Cu1 N2 C6 C7 -177.06(15) . . . . ?
C10 N2 C6 C5 -175.87(17) . . . . ?
Cu1 N2 C6 C5 5.5(2) . . . . ?
C8 C7 C6 N2 -2.3(3) . . . . ?
C8 C7 C6 C5 174.9(2) . . . . ?
Cu1 O3 N3 O1 -121.56(19) . . . . ?
Cu1 O3 N3 O2 60.2(2) . . . . ?
Cu1 O4 C12 C13 -2.4(3) . . . . ?
Cu1 O4 C12 C11 177.18(15) . . . . ?
C14 C13 C12 O4 2.3(4) . . . . ?
C14 C13 C12 C11 -177.3(2) . . . . ?
C6 N2 C10 C9 0.4(3) . . . . ?
Cu1 N2 C10 C9 178.90(15) . . . . ?
C1 N1 C5 C4 -2.2(3) . . . . ?
Cu1 N1 C5 C4 174.67(15) . . . . ?
C1 N1 C5 C6 176.35(18) . . . . ?
Cu1 N1 C5 C6 -6.8(2) . . . . ?
N2 C6 C5 N1 0.8(2) . . . . ?
C7 C6 C5 N1 -176.54(19) . . . . ?
N2 C6 C5 C4 179.35(18) . . . . ?
C7 C6 C5 C4 2.0(3) . . . . ?
N1 C5 C4 C3 3.0(3) . . . . ?
C6 C5 C4 C3 -175.41(19) . . . . ?
C5 N1 C1 C2 -0.2(3) . . . . ?
Cu1 N1 C1 C2 -176.74(16) . . . . ?
Cu1 O5 C14 C13 -1.0(3) . . . . ?
Cu1 O5 C14 C15 179.94(15) . . . . ?
C12 C13 C14 O5 -0.4(4) . . . . ?
C12 C13 C14 C15 178.6(2) . . . . ?
C5 C4 C3 C2 -1.3(3) . . . . ?
C4 C3 C2 C1 -1.0(3) . . . . ?
N1 C1 C2 C3 1.8(3) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
N2 C10 C9 C8 -1.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.055
