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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1443872'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 Cu N2 O5'
_chemical_formula_weight         411.93

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                   21.607(4)
_cell_length_b                   6.2550(13)
_cell_length_c                   26.077(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3524.3(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    7527
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1720
_exptl_absorpt_coefficient_mu    1.272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7850
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            33033
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         27.90
_reflns_number_total             4209
_reflns_number_gt                3748
_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)+(0.0542P)²+4.6449P] 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       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4209
_refine_ls_number_parameters     244
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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 0.125061(15) 0.20076(6) 0.317153(13) 0.01909(14) Uani 1 1 d . . .
C7 C 0.12881(14) 0.2576(6) 0.04798(12) 0.0308(7) Uani 1 1 d . . .
H7A H 0.1127 0.1647 0.0235 0.037 Uiso 1 1 calc R . .
O3 O 0.17146(9) 0.2989(3) 0.37680(8) 0.0231(4) Uani 1 1 d . . .
O1 O 0.16298(9) 0.4252(3) 0.27793(7) 0.0252(5) Uani 1 1 d . . .
C8 C 0.12141(14) 0.2133(5) 0.09886(12) 0.0262(7) Uani 1 1 d . . .
H8A H 0.1003 0.0899 0.1083 0.031 Uiso 1 1 calc R . .
O4 O 0.10504(10) 0.5509(3) 0.40195(9) 0.0311(5) Uani 1 1 d . . .
C1 C 0.16471(12) 0.4488(5) 0.22789(11) 0.0216(6) Uani 1 1 d . . .
N1 N 0.09506(11) 0.0649(4) 0.25561(9) 0.0197(5) Uani 1 1 d . . .
C10 C 0.13865(12) 0.3056(4) 0.19217(11) 0.0184(5) Uani 1 1 d . . .
N2 N 0.07495(11) -0.0240(4) 0.35437(9) 0.0204(5) Uani 1 1 d . . .
H2C H 0.1018 -0.1329 0.3608 0.024 Uiso 1 1 calc R . .
C17 C 0.15604(13) 0.4595(4) 0.40451(10) 0.0214(6) Uani 1 1 d . . .
C11 C 0.10519(12) 0.1196(4) 0.20863(10) 0.0185(5) Uani 1 1 d . . .
H11A H 0.0894 0.0307 0.1832 0.022 Uiso 1 1 calc R . .
C15 C -0.00722(14) 0.1855(5) 0.40122(11) 0.0237(6) Uani 1 1 d . . .
H15A H -0.0433 0.1055 0.3889 0.028 Uiso 1 1 calc R . .
C13 C 0.02949(14) -0.1112(5) 0.31748(10) 0.0229(6) Uani 1 1 d . . .
H13A H -0.0056 -0.0151 0.3145 0.027 Uiso 1 1 calc R . .
H13B H 0.0145 -0.2489 0.3293 0.027 Uiso 1 1 calc R . .
O2 O 0.00460(10) 0.3535(3) 0.36550(8) 0.0269(5) Uani 1 1 d . . .
H2B H 0.0352 0.4212 0.3747 0.040 Uiso 1 1 calc R . .
C3 C 0.20028(13) 0.6786(5) 0.15866(12) 0.0259(6) Uani 1 1 d . . .
H3A H 0.2198 0.8035 0.1481 0.031 Uiso 1 1 calc R . .
C4 C 0.17623(12) 0.5372(5) 0.12119(11) 0.0225(6) Uani 1 1 d . . .
C18 C 0.20375(15) 0.5339(5) 0.44233(11) 0.0278(6) Uani 1 1 d . . .
H18A H 0.1879 0.6541 0.4611 0.042 Uiso 1 1 calc R . .
H18B H 0.2406 0.5754 0.4244 0.042 Uiso 1 1 calc R . .
H18C H 0.2132 0.4200 0.4657 0.042 Uiso 1 1 calc R . .
C5 C 0.18350(14) 0.5792(5) 0.06818(12) 0.0276(6) Uani 1 1 d . . .
H5A H 0.2043 0.7021 0.0578 0.033 Uiso 1 1 calc R . .
C6 C 0.16073(15) 0.4435(6) 0.03212(12) 0.0327(7) Uani 1 1 d . . .
H6A H 0.1661 0.4726 -0.0026 0.039 Uiso 1 1 calc R . .
C9 C 0.14488(12) 0.3491(5) 0.13769(11) 0.0211(6) Uani 1 1 d . . .
C12 C 0.06109(14) -0.1353(5) 0.26611(10) 0.0227(6) Uani 1 1 d . . .
H12A H 0.0895 -0.2552 0.2669 0.027 Uiso 1 1 calc R . .
H12B H 0.0306 -0.1610 0.2395 0.027 Uiso 1 1 calc R . .
C2 C 0.19557(13) 0.6365(5) 0.20953(12) 0.0253(6) Uani 1 1 d . . .
H2A H 0.2127 0.7315 0.2330 0.030 Uiso 1 1 calc R . .
C16 C -0.02224(16) 0.2694(5) 0.45442(12) 0.0321(7) Uani 1 1 d . . .
H16A H -0.0563 0.3674 0.4524 0.048 Uiso 1 1 calc R . .
H16B H 0.0133 0.3417 0.4682 0.048 Uiso 1 1 calc R . .
H16C H -0.0331 0.1521 0.4764 0.048 Uiso 1 1 calc R . .
C14 C 0.04697(14) 0.0303(5) 0.40450(10) 0.0237(6) Uani 1 1 d . . .
H14A H 0.0786 0.0923 0.4263 0.028 Uiso 1 1 calc R . .
H14B H 0.0329 -0.1004 0.4208 0.028 Uiso 1 1 calc R . .
O5 O 0.20128(11) 0.8139(4) 0.33132(9) 0.0312(5) Uani 1 1 d D . .
H5B H 0.196(2) 0.690(3) 0.3180(15) 0.058(15) Uiso 1 1 d D . .
H5C H 0.2385(10) 0.822(10) 0.342(2) 0.11(2) Uiso 1 1 d 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 O1 1.921(2) . ?
Cu1 N1 1.928(2) . ?
Cu1 O3 1.950(2) . ?
Cu1 N2 2.023(2) . ?
C7 C8 1.365(4) . ?
C7 C6 1.414(5) . ?
O3 C17 1.281(3) . ?
O1 C1 1.314(3) . ?
C8 C9 1.416(4) . ?
O4 C17 1.243(3) . ?
C1 C10 1.410(4) . ?
C1 C2 1.432(4) . ?
N1 C11 1.291(3) . ?
N1 C12 1.477(4) . ?
C10 C11 1.435(4) . ?
C10 C9 1.453(4) . ?
N2 C13 1.479(3) . ?
N2 C14 1.480(3) . ?
C17 C18 1.501(4) . ?
C15 O2 1.428(3) . ?
C15 C16 1.518(4) . ?
C15 C14 1.523(4) . ?
C13 C12 1.511(4) . ?
C3 C2 1.356(4) . ?
C3 C4 1.417(4) . ?
C4 C5 1.416(4) . ?
C4 C9 1.424(4) . ?
C5 C6 1.359(5) . ?

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 N1 91.29(9) . . ?
O1 Cu1 O3 88.58(9) . . ?
N1 Cu1 O3 167.33(9) . . ?
O1 Cu1 N2 172.77(9) . . ?
N1 Cu1 N2 85.01(9) . . ?
O3 Cu1 N2 96.40(9) . . ?
C8 C7 C6 120.6(3) . . ?
C17 O3 Cu1 124.27(18) . . ?
C1 O1 Cu1 128.55(18) . . ?
C7 C8 C9 122.1(3) . . ?
O1 C1 C10 125.0(3) . . ?
O1 C1 C2 115.9(3) . . ?
C10 C1 C2 119.1(3) . . ?
C11 N1 C12 119.0(2) . . ?
C11 N1 Cu1 128.0(2) . . ?
C12 N1 Cu1 112.73(17) . . ?
C1 C10 C11 121.3(3) . . ?
C1 C10 C9 119.3(3) . . ?
C11 C10 C9 119.4(2) . . ?
C13 N2 C14 112.8(2) . . ?
C13 N2 Cu1 107.44(17) . . ?
C14 N2 Cu1 118.87(18) . . ?
O4 C17 O3 124.1(3) . . ?
O4 C17 C18 120.1(3) . . ?
O3 C17 C18 115.8(3) . . ?
N1 C11 C10 125.7(3) . . ?
O2 C15 C16 112.3(2) . . ?
O2 C15 C14 111.6(2) . . ?
C16 C15 C14 109.5(2) . . ?
N2 C13 C12 108.3(2) . . ?
C2 C3 C4 121.7(3) . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 C9 118.8(3) . . ?
C5 C4 C9 120.1(3) . . ?
C6 C5 C4 121.3(3) . . ?
C5 C6 C7 119.2(3) . . ?
C8 C9 C4 116.7(3) . . ?
C8 C9 C10 123.6(3) . . ?
C4 C9 C10 119.6(3) . . ?
N1 C12 C13 107.7(2) . . ?
C3 C2 C1 121.4(3) . . ?
N2 C14 C15 114.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.90
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.127
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.098

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1443873'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-04-25 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 H24 Cu N2 O7'
_chemical_formula_weight         467.95

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                   11.6184(12)
_cell_length_b                   16.4826(18)
_cell_length_c                   12.0036(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.565(2)
_cell_angle_gamma                90.00
_cell_volume                     2252.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    386(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             972
_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8234
_exptl_absorpt_correction_T_max  0.8883
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      386(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22531
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.53
_reflns_number_total             5132
_reflns_number_gt                4749
_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)+(0.0678P)²+1.4687P] 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         5132
_refine_ls_number_parameters     307
_refine_ls_number_restraints     400
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.175
_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 0.61492(2) 1.020320(14) 0.60991(2) 0.02388(11) Uani 1 1 d . . .
C3 C 0.8105(2) 0.81998(15) 0.35573(19) 0.0318(4) Uani 1 1 d U . .
H3A H 0.8518 0.8149 0.2973 0.038 Uiso 1 1 calc R . .
C10 C 0.68980(17) 0.83809(12) 0.53594(17) 0.0235(4) Uani 1 1 d U . .
C4 C 0.79260(19) 0.75026(14) 0.41930(19) 0.0291(4) Uani 1 1 d U . .
C9 C 0.72919(17) 0.75818(12) 0.50849(17) 0.0249(4) Uani 1 1 d U . .
C1 C 0.70805(18) 0.90596(13) 0.46957(18) 0.0253(4) Uani 1 1 d U . .
C2 C 0.76887(19) 0.89387(14) 0.37787(19) 0.0297(4) Uani 1 1 d U . .
H2A H 0.7800 0.9378 0.3326 0.036 Uiso 1 1 calc R . .
C8 C 0.7084(2) 0.68640(13) 0.56645(19) 0.0310(4) Uani 1 1 d U . .
H8A H 0.6633 0.6889 0.6222 0.037 Uiso 1 1 calc R . .
C7 C 0.7538(2) 0.61307(15) 0.5415(2) 0.0401(5) Uani 1 1 d U . .
H7A H 0.7399 0.5670 0.5815 0.048 Uiso 1 1 calc R . .
C5 C 0.8378(2) 0.67384(16) 0.3958(2) 0.0396(5) Uani 1 1 d U . .
H5A H 0.8798 0.6694 0.3379 0.048 Uiso 1 1 calc R . .
C6 C 0.8209(3) 0.60662(16) 0.4567(2) 0.0448(6) Uani 1 1 d U . .
H6A H 0.8533 0.5571 0.4422 0.054 Uiso 1 1 calc R . .
O1 O 0.67506(16) 0.97969(9) 0.48548(14) 0.0306(4) Uani 1 1 d . . .
N1 N 0.60064(15) 0.91301(10) 0.67283(14) 0.0231(3) Uani 1 1 d . . .
C11 C 0.63778(17) 0.84684(12) 0.63413(17) 0.0233(4) Uani 1 1 d U . .
H11A H 0.6299 0.7996 0.6744 0.028 Uiso 1 1 calc R . .
O3 O 0.54466(13) 1.07855(9) 0.72281(12) 0.0262(3) Uani 1 1 d . . .
O4 O 0.61564(14) 1.12936(9) 0.54120(12) 0.0278(3) Uani 1 1 d . . .
O5 O 0.51306(17) 1.20425(10) 0.77500(15) 0.0391(4) Uani 1 1 d . . .
O6 O 0.6012(2) 1.25879(11) 0.59151(16) 0.0500(5) Uani 1 1 d . . .
C12 C 0.55271(18) 0.90564(13) 0.77710(17) 0.0250(4) Uani 1 1 d U . .
H12A H 0.5894 0.9458 0.8319 0.030 Uiso 1 1 calc R . .
H12B H 0.5714 0.8524 0.8102 0.030 Uiso 1 1 calc R . .
C18 C 0.54426(19) 1.15518(13) 0.71037(18) 0.0265(4) Uani 1 1 d U . .
C13 C 0.42066(19) 0.91756(13) 0.75313(18) 0.0273(4) Uani 1 1 d U . .
H13A H 0.3937 0.9206 0.8245 0.033 Uiso 1 1 calc R . .
H13B H 0.4012 0.9684 0.7130 0.033 Uiso 1 1 calc R . .
C17 C 0.5904(2) 1.18568(13) 0.60541(18) 0.0294(4) Uani 1 1 d U . .
N3 N 0.35954(16) 0.84970(11) 0.68346(15) 0.0278(4) Uani 1 1 d . . .
H3B H 0.3944 0.8149 0.6483 0.033 Uiso 1 1 calc R . .
C14 C 0.2311(2) 0.84905(18) 0.6817(2) 0.0417(6) Uani 1 1 d U . .
H14A H 0.1955 0.8965 0.6410 0.050 Uiso 1 1 calc R . .
H14B H 0.2187 0.8524 0.7591 0.050 Uiso 1 1 calc R . .
C15 C 0.1713(2) 0.77385(18) 0.6258(3) 0.0459(6) Uani 1 1 d U . .
C16 C 0.0434(3) 0.7737(3) 0.6367(4) 0.0691(10) Uani 1 1 d DU . .
H16A H 0.0055 0.7258 0.6013 0.104 Uiso 1 1 calc R . .
H16B H 0.0049 0.8209 0.5999 0.104 Uiso 1 1 calc R . .
H16C H 0.0388 0.7743 0.7157 0.104 Uiso 1 1 calc R . .
O7 O 0.80120(19) 1.05715(17) 0.7319(2) 0.0624(6) Uani 1 1 d DU . .
H7B H 0.8051 1.0669 0.8089 0.094 Uiso 1 1 calc RD . .
C20 C 0.9057(4) 1.0638(4) 0.6844(6) 0.0938(14) Uani 1 1 d U . .
C19A C 0.9636(7) 0.9842(4) 0.6970(9) 0.067(2) Uani 0.50 1 d PU . .
O2 O 0.2237(3) 0.6981(2) 0.6674(3) 0.0444(7) Uani 0.60 1 d PD . .
O2' O 0.1771(4) 0.7634(3) 0.5196(4) 0.0401(10) Uani 0.40 1 d PD . .
C19B C 0.9092(17) 1.0067(11) 0.7049(17) 0.053(3) Uani 0.20 1 d PU . .
C19C C 1.0006(13) 1.0143(11) 0.7778(18) 0.055(3) Uani 0.20 1 d PU . .
C19D C 0.930(2) 1.057(2) 0.607(3) 0.051(4) Uani 0.10 1 d PU . .


_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 1.8937(16) . ?
Cu1 N1 1.9434(17) . ?
Cu1 O3 1.9666(14) . ?
Cu1 O4 1.9782(15) . ?
Cu1 O7 2.435(2) . ?
C3 C2 1.356(3) . ?
C3 C4 1.418(3) . ?
C10 C1 1.414(3) . ?
C10 C11 1.436(3) . ?
C10 C9 1.454(3) . ?
C4 C5 1.414(3) . ?
C4 C9 1.422(3) . ?
C9 C8 1.418(3) . ?
C1 O1 1.300(3) . ?
C1 C2 1.436(3) . ?
C8 C7 1.376(3) . ?
C7 C6 1.405(4) . ?
C5 C6 1.363(4) . ?
N1 C11 1.293(3) . ?
N1 C12 1.473(2) . ?
O3 C18 1.272(3) . ?
O4 C17 1.278(3) . ?
O5 C18 1.225(3) . ?
O6 C17 1.227(3) . ?
C12 C13 1.516(3) . ?
C18 C17 1.549(3) . ?
C13 N3 1.489(3) . ?
N3 C14 1.488(3) . ?
C14 C15 1.511(4) . ?
C15 O2' 1.303(5) . ?
C15 O2 1.434(4) . ?
C15 C16 1.517(4) . ?
O7 C20 1.446(5) . ?
C20 C19B 0.972(17) . ?
C20 C19D 1.03(3) . ?
C20 C19A 1.469(9) . ?
C20 C19C 1.626(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 93.35(7) . . ?
O1 Cu1 O3 170.36(6) . . ?
N1 Cu1 O3 95.55(7) . . ?
O1 Cu1 O4 87.68(6) . . ?
N1 Cu1 O4 175.39(7) . . ?
O3 Cu1 O4 83.16(6) . . ?
O1 Cu1 O7 97.97(9) . . ?
N1 Cu1 O7 97.35(8) . . ?
O3 Cu1 O7 84.57(8) . . ?
O4 Cu1 O7 86.95(8) . . ?
C2 C3 C4 121.8(2) . . ?
C1 C10 C11 121.23(18) . . ?
C1 C10 C9 119.97(18) . . ?
C11 C10 C9 118.73(18) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 C9 120.0(2) . . ?
C3 C4 C9 118.99(19) . . ?
C8 C9 C4 117.26(19) . . ?
C8 C9 C10 123.53(19) . . ?
C4 C9 C10 119.21(19) . . ?
O1 C1 C10 125.10(18) . . ?
O1 C1 C2 116.56(19) . . ?
C10 C1 C2 118.33(19) . . ?
C3 C2 C1 121.6(2) . . ?
C7 C8 C9 121.0(2) . . ?
C8 C7 C6 121.1(2) . . ?
C6 C5 C4 121.2(2) . . ?
C5 C6 C7 119.2(2) . . ?
C1 O1 Cu1 127.79(14) . . ?
C11 N1 C12 116.48(17) . . ?
C11 N1 Cu1 124.56(14) . . ?
C12 N1 Cu1 118.78(13) . . ?
N1 C11 C10 127.27(19) . . ?
C18 O3 Cu1 113.33(13) . . ?
C17 O4 Cu1 112.83(13) . . ?
N1 C12 C13 111.62(17) . . ?
O5 C18 O3 125.2(2) . . ?
O5 C18 C17 119.71(19) . . ?
O3 C18 C17 115.09(18) . . ?
N3 C13 C12 111.09(17) . . ?
O6 C17 O4 126.1(2) . . ?
O6 C17 C18 119.41(19) . . ?
O4 C17 C18 114.44(18) . . ?
C14 N3 C13 112.18(18) . . ?
N3 C14 C15 112.6(2) . . ?
O2' C15 O2 97.1(3) . . ?
O2' C15 C14 115.6(3) . . ?
O2 C15 C14 115.7(2) . . ?
O2' C15 C16 109.2(3) . . ?
O2 C15 C16 108.9(3) . . ?
C14 C15 C16 109.6(3) . . ?
C20 O7 Cu1 119.8(3) . . ?
C19B C20 C19D 97(2) . . ?
C19B C20 O7 79.7(13) . . ?
C19D C20 O7 138.5(17) . . ?
C19B C20 C19A 27.6(11) . . ?
C19D C20 C19A 78.2(19) . . ?
O7 C20 C19A 107.1(5) . . ?
C19B C20 C19C 49.5(13) . . ?
C19D C20 C19C 108(2) . . ?
O7 C20 C19C 101.3(6) . . ?
C19A C20 C19C 41.2(8) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.079


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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1443874'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 Cu N2 O4'
_chemical_formula_weight         455.98

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   Cc

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'

_cell_length_a                   25.619(7)
_cell_length_b                   10.632(3)
_cell_length_c                   7.5173(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.056(5)
_cell_angle_gamma                90.00
_cell_volume                     2022.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    113
_cell_measurement_reflns_used    3872
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             948
_exptl_absorpt_coefficient_mu    1.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8080
_exptl_absorpt_correction_T_max  0.8780
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12682
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4492
_reflns_number_gt                4337
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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)+(0.0305P)²+0.0894P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.026(7)
_refine_ls_number_reflns         4492
_refine_ls_number_parameters     275
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0530
_refine_ls_wR_factor_gt          0.0528
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.341343(15) 0.252270(14) 0.10377(4) 0.01360(5) Uani 1 1 d . . .
O1 O 0.37164(4) 0.35897(10) -0.06095(15) 0.0162(2) Uani 1 1 d . . .
N1 N 0.40986(5) 0.17758(11) 0.19126(18) 0.0156(2) Uani 1 1 d . . .
N2 N 0.31881(5) 0.16387(12) 0.31455(19) 0.0160(3) Uani 1 1 d . . .
C11 C 0.44884(6) 0.17294(13) 0.1028(2) 0.0158(3) Uani 1 1 d . . .
H11A H 0.4774 0.1223 0.1491 0.019 Uiso 1 1 calc R . .
C1 C 0.41529(6) 0.33507(13) -0.1250(2) 0.0149(3) Uani 1 1 d . . .
C3 C 0.46892(6) 0.39398(15) -0.3522(2) 0.0205(3) Uani 1 1 d . . .
H3A H 0.4752 0.4480 -0.4438 0.025 Uiso 1 1 calc R . .
C4 C 0.50436(6) 0.29196(15) -0.3022(2) 0.0188(3) Uani 1 1 d . . .
C22 C 0.20544(6) 0.15459(14) -0.23499(19) 0.0140(3) Uani 1 1 d . . .
C9 C 0.49582(6) 0.21328(15) -0.1577(2) 0.0167(3) Uani 1 1 d . . .
C23 C 0.26134(6) 0.17086(13) -0.1394(2) 0.0135(3) Uani 1 1 d . . .
C2 C 0.42629(6) 0.41427(14) -0.2698(2) 0.0182(3) Uani 1 1 d . . .
H2A H 0.4037 0.4808 -0.3076 0.022 Uiso 1 1 calc R . .
C7 C 0.57334(6) 0.09269(16) -0.2049(2) 0.0243(3) Uani 1 1 d . . .
H7A H 0.5964 0.0262 -0.1721 0.029 Uiso 1 1 calc R . .
C10 C 0.45204(7) 0.23937(12) -0.0615(2) 0.0153(3) Uani 1 1 d . . .
C20 C 0.11462(7) 0.22342(16) -0.2928(2) 0.0201(3) Uani 1 1 d . . .
H20A H 0.0886 0.2805 -0.2735 0.024 Uiso 1 1 calc R . .
C8 C 0.53115(6) 0.11078(15) -0.1147(2) 0.0196(3) Uani 1 1 d . . .
H8A H 0.5257 0.0550 -0.0241 0.023 Uiso 1 1 calc R . .
C18 C 0.14065(6) 0.03702(16) -0.4360(2) 0.0212(3) Uani 1 1 d . . .
H18A H 0.1321 -0.0308 -0.5132 0.025 Uiso 1 1 calc R . .
C17 C 0.19213(6) 0.05333(14) -0.3504(2) 0.0176(3) Uani 1 1 d . . .
H17A H 0.2180 -0.0040 -0.3701 0.021 Uiso 1 1 calc R . .
C6 C 0.58207(7) 0.17255(17) -0.3448(3) 0.0274(4) Uani 1 1 d . . .
H6A H 0.6108 0.1597 -0.4043 0.033 Uiso 1 1 calc R . .
C19 C 0.10171(6) 0.12210(16) -0.4067(2) 0.0219(3) Uani 1 1 d . . .
H19A H 0.0671 0.1109 -0.4634 0.026 Uiso 1 1 calc R . .
C14 C 0.27414(7) 0.22795(16) 0.3791(3) 0.0212(3) Uani 1 1 d . . .
H14A H 0.2650 0.1822 0.4815 0.025 Uiso 1 1 calc R . .
H14B H 0.2437 0.2263 0.2845 0.025 Uiso 1 1 calc R . .
C21 C 0.16630(7) 0.24032(13) -0.2069(2) 0.0167(3) Uani 1 1 d . . .
H21A H 0.1748 0.3088 -0.1308 0.020 Uiso 1 1 calc R . .
C12 C 0.41089(6) 0.10325(14) 0.3569(2) 0.0180(3) Uani 1 1 d . . .
H12A H 0.4448 0.1127 0.4340 0.022 Uiso 1 1 calc R . .
H12B H 0.4055 0.0149 0.3277 0.022 Uiso 1 1 calc R . .
C5 C 0.54776(8) 0.27033(17) -0.3935(3) 0.0254(4) Uani 1 1 d . . .
H5A H 0.5531 0.3230 -0.4877 0.031 Uiso 1 1 calc R . .
C13 C 0.36686(6) 0.15171(15) 0.4517(2) 0.0192(3) Uani 1 1 d . . .
H13A H 0.3605 0.0935 0.5453 0.023 Uiso 1 1 calc R . .
H13B H 0.3764 0.2327 0.5067 0.023 Uiso 1 1 calc R . .
O4 O 0.29654(4) 0.09668(10) -0.16875(16) 0.0210(2) Uani 1 1 d . . .
O3 O 0.26924(5) 0.26257(9) -0.02900(17) 0.0173(2) Uani 1 1 d . . .
O2 O 0.31623(5) 0.41723(11) 0.30663(16) 0.0221(3) Uani 1 1 d . . .
H2B H 0.3314 0.4808 0.3496 0.033 Uiso 1 1 calc R . .
C15 C 0.28646(7) 0.36350(16) 0.4341(3) 0.0251(4) Uani 1 1 d . . .
H15A H 0.3084 0.3640 0.5532 0.030 Uiso 1 1 calc R . .
C16 C 0.23612(7) 0.43433(15) 0.4454(3) 0.0273(4) Uani 1 1 d . . .
H16A H 0.2444 0.5198 0.4802 0.041 Uiso 1 1 calc R . .
H16B H 0.2180 0.3952 0.5333 0.041 Uiso 1 1 calc R . .
H16C H 0.2139 0.4331 0.3300 0.041 Uiso 1 1 calc R . .
H2C H 0.3093(7) 0.0980(19) 0.292(3) 0.012(5) 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 O1 1.9300(11) . ?
Cu1 N1 1.9446(14) . ?
Cu1 O3 1.9597(13) . ?
Cu1 N2 2.0037(14) . ?
O1 C1 1.3101(18) . ?
N1 C11 1.2847(19) . ?
N1 C12 1.471(2) . ?
N2 C14 1.478(2) . ?
N2 C13 1.482(2) . ?
C11 C10 1.436(2) . ?
C1 C10 1.417(2) . ?
C1 C2 1.439(2) . ?
C3 C2 1.355(2) . ?
C3 C4 1.426(2) . ?
C4 C5 1.414(2) . ?
C4 C9 1.416(2) . ?
C22 C17 1.391(2) . ?
C22 C21 1.395(2) . ?
C22 C23 1.508(2) . ?
C9 C8 1.421(2) . ?
C9 C10 1.454(2) . ?
C23 O4 1.2436(17) . ?
C23 O3 1.2757(18) . ?
C7 C8 1.377(2) . ?
C7 C6 1.397(2) . ?
C20 C19 1.383(2) . ?
C20 C21 1.390(3) . ?
C18 C17 1.384(2) . ?
C18 C19 1.390(2) . ?
C6 C5 1.373(3) . ?
C14 C15 1.519(2) . ?
C12 C13 1.516(2) . ?
O2 C15 1.434(2) . ?
C15 C16 1.507(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
O1 Cu1 N1 91.39(5) . . ?
O1 Cu1 O3 94.73(5) . . ?
N1 Cu1 O3 157.45(5) . . ?
O1 Cu1 N2 167.96(5) . . ?
N1 Cu1 N2 84.15(6) . . ?
O3 Cu1 N2 93.62(6) . . ?
C1 O1 Cu1 125.06(9) . . ?
C11 N1 C12 120.36(13) . . ?
C11 N1 Cu1 125.06(11) . . ?
C12 N1 Cu1 113.61(10) . . ?
C14 N2 C13 114.40(14) . . ?
C14 N2 Cu1 112.21(10) . . ?
C13 N2 Cu1 106.26(9) . . ?
N1 C11 C10 125.48(14) . . ?
O1 C1 C10 125.16(14) . . ?
O1 C1 C2 116.40(13) . . ?
C10 C1 C2 118.43(14) . . ?
C2 C3 C4 121.73(14) . . ?
C5 C4 C9 120.31(16) . . ?
C5 C4 C3 120.82(15) . . ?
C9 C4 C3 118.86(14) . . ?
C17 C22 C21 119.22(14) . . ?
C17 C22 C23 120.49(13) . . ?
C21 C22 C23 120.28(14) . . ?
C4 C9 C8 117.25(14) . . ?
C4 C9 C10 119.59(14) . . ?
C8 C9 C10 123.16(14) . . ?
O4 C23 O3 123.71(14) . . ?
O4 C23 C22 120.23(13) . . ?
O3 C23 C22 116.06(13) . . ?
C3 C2 C1 121.39(14) . . ?
C8 C7 C6 121.14(16) . . ?
C1 C10 C11 121.19(15) . . ?
C1 C10 C9 119.56(15) . . ?
C11 C10 C9 119.13(14) . . ?
C19 C20 C21 120.34(15) . . ?
C7 C8 C9 121.09(15) . . ?
C17 C18 C19 119.97(15) . . ?
C18 C17 C22 120.61(14) . . ?
C5 C6 C7 119.29(16) . . ?
C20 C19 C18 119.85(15) . . ?
N2 C14 C15 112.84(14) . . ?
C20 C21 C22 120.01(15) . . ?
N1 C12 C13 107.44(12) . . ?
C6 C5 C4 120.86(17) . . ?
N2 C13 C12 107.50(13) . . ?
C23 O3 Cu1 109.20(10) . . ?
O2 C15 C16 112.86(14) . . ?
O2 C15 C14 107.82(14) . . ?
C16 C15 C14 110.27(15) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.039

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1443875'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 Cu N2 O5'
_chemical_formula_weight         470.97

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   Cc

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'

_cell_length_a                   25.496(3)
_cell_length_b                   10.9096(11)
_cell_length_c                   7.4583(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.245(2)
_cell_angle_gamma                90.00
_cell_volume                     2034.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    386(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    1.113
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8081
_exptl_absorpt_correction_T_max  0.8420
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      386(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12785
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4382
_reflns_number_gt                4243
_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)+(0.0328P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(7)
_refine_ls_number_reflns         4382
_refine_ls_number_parameters     284
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0181
_refine_ls_R_factor_gt           0.0176
_refine_ls_wR_factor_ref         0.0500
_refine_ls_wR_factor_gt          0.0498
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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 0.732962(14) 0.747096(14) 0.68400(4) 0.00975(5) Uani 1 1 d . . .
O3 O 0.68559(4) 0.90442(10) 0.42112(16) 0.0170(2) Uani 1 1 d . . .
O1 O 0.76260(4) 0.63933(10) 0.52560(15) 0.0118(2) Uani 1 1 d . . .
N2 N 0.71117(5) 0.83947(12) 0.89037(19) 0.0112(3) Uani 1 1 d . . .
O2 O 0.65863(5) 0.73463(9) 0.54062(17) 0.0128(2) Uani 1 1 d . . .
N1 N 0.80179(5) 0.82471(11) 0.76936(17) 0.0114(2) Uani 1 1 d . . .
C11 C 0.83998(6) 0.82854(13) 0.6790(2) 0.0124(3) Uani 1 1 d . . .
H11A H 0.8687 0.8798 0.7229 0.015 Uiso 1 1 calc R . .
C23 C 0.64972(6) 0.83057(13) 0.4363(2) 0.0108(3) Uani 1 1 d . . .
C2 C 0.81511(6) 0.58406(14) 0.3146(2) 0.0140(3) Uani 1 1 d . . .
H2A H 0.7931 0.5165 0.2818 0.017 Uiso 1 1 calc R . .
C9 C 0.88388(6) 0.78605(14) 0.4150(2) 0.0125(3) Uani 1 1 d . . .
C4 C 0.89082(6) 0.70745(14) 0.2698(2) 0.0146(3) Uani 1 1 d . . .
C3 C 0.85605(6) 0.60514(14) 0.2262(2) 0.0160(3) Uani 1 1 d . . .
H3A H 0.8615 0.5513 0.1348 0.019 Uiso 1 1 calc R . .
C1 C 0.80507(6) 0.66354(13) 0.4576(2) 0.0118(3) Uani 1 1 d . . .
C8 C 0.91878(6) 0.88757(14) 0.4526(2) 0.0155(3) Uani 1 1 d . . .
H8A H 0.9143 0.9424 0.5439 0.019 Uiso 1 1 calc R . .
C22 C 0.55246(7) 0.76629(13) 0.3543(2) 0.0123(3) Uani 1 1 d . . .
C21 C 0.50005(6) 0.78995(15) 0.2653(2) 0.0163(3) Uani 1 1 d . . .
H21A H 0.4729 0.7355 0.2773 0.020 Uiso 1 1 calc R . .
C17 C 0.59344(6) 0.84914(13) 0.3380(2) 0.0111(3) Uani 1 1 d . . .
C12 C 0.80399(6) 0.90169(14) 0.9328(2) 0.0128(3) Uani 1 1 d . . .
H12A H 0.7980 0.9870 0.8978 0.015 Uiso 1 1 calc R . .
H12B H 0.8388 0.8947 1.0126 0.015 Uiso 1 1 calc R . .
C19 C 0.52858(6) 0.97600(15) 0.1396(2) 0.0189(3) Uani 1 1 d . . .
H19A H 0.5206 1.0455 0.0672 0.023 Uiso 1 1 calc R . .
C10 C 0.84167(6) 0.75996(12) 0.5159(2) 0.0116(3) Uani 1 1 d . . .
C20 C 0.48836(6) 0.89362(16) 0.1595(2) 0.0182(3) Uani 1 1 d . . .
H20A H 0.4533 0.9087 0.1008 0.022 Uiso 1 1 calc R . .
C7 C 0.95914(6) 0.90710(15) 0.3575(2) 0.0189(3) Uani 1 1 d . . .
H7A H 0.9821 0.9733 0.3879 0.023 Uiso 1 1 calc R . .
C6 C 0.96612(7) 0.82817(16) 0.2147(3) 0.0216(4) Uani 1 1 d . . .
H6A H 0.9934 0.8419 0.1506 0.026 Uiso 1 1 calc R . .
C5 C 0.93203(7) 0.73064(16) 0.1716(3) 0.0197(4) Uani 1 1 d . . .
H5A H 0.9361 0.6788 0.0761 0.024 Uiso 1 1 calc R . .
C13 C 0.76056(6) 0.85694(14) 1.0300(2) 0.0137(3) Uani 1 1 d . . .
H13A H 0.7712 0.7802 1.0921 0.016 Uiso 1 1 calc R . .
H13B H 0.7545 0.9167 1.1200 0.016 Uiso 1 1 calc R . .
C18 C 0.58029(6) 0.95315(14) 0.2288(2) 0.0152(3) Uani 1 1 d . . .
H18A H 0.6071 1.0083 0.2160 0.018 Uiso 1 1 calc R . .
O4 O 0.56151(4) 0.66244(10) 0.45529(17) 0.0175(2) Uani 1 1 d . . .
C14 C 0.66758(6) 0.77861(15) 0.9611(2) 0.0133(3) Uani 1 1 d . . .
H14A H 0.6361 0.7736 0.8643 0.016 Uiso 1 1 calc R . .
H14B H 0.6585 0.8275 1.0593 0.016 Uiso 1 1 calc R . .
C15 C 0.68338(6) 0.64998(13) 1.0320(2) 0.0135(3) Uani 1 1 d . . .
H15A H 0.7080 0.6558 1.1502 0.016 Uiso 1 1 calc R . .
O5 O 0.71022(5) 0.59305(10) 0.90091(16) 0.0149(2) Uani 1 1 d . . .
H5B H 0.7240 0.5287 0.9432 0.022 Uiso 1 1 calc R . .
C16 C 0.63394(7) 0.57887(15) 1.0550(2) 0.0185(3) Uani 1 1 d . . .
H16A H 0.6441 0.4980 1.0994 0.028 Uiso 1 1 calc R . .
H16B H 0.6098 0.5731 0.9392 0.028 Uiso 1 1 calc R . .
H16C H 0.6166 0.6205 1.1409 0.028 Uiso 1 1 calc R . .
H2B H 0.7000(9) 0.895(2) 0.863(3) 0.020(6) 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 O1 1.9228(11) . ?
Cu1 N1 1.9407(13) . ?
Cu1 O2 1.9907(12) . ?
Cu1 N2 2.0067(14) . ?
O3 C23 1.2404(18) . ?
O1 C1 1.3093(18) . ?
N2 C14 1.477(2) . ?
N2 C13 1.481(2) . ?
O2 C23 1.2976(18) . ?
N1 C11 1.288(2) . ?
N1 C12 1.4722(19) . ?
C11 C10 1.436(2) . ?
C23 C17 1.492(2) . ?
C2 C3 1.359(2) . ?
C2 C1 1.435(2) . ?
C9 C8 1.414(2) . ?
C9 C4 1.419(2) . ?
C9 C10 1.457(2) . ?
C4 C5 1.416(2) . ?
C4 C3 1.423(2) . ?
C1 C10 1.417(2) . ?
C8 C7 1.376(2) . ?
C22 O4 1.3551(18) . ?
C22 C21 1.395(2) . ?
C22 C17 1.405(2) . ?
C21 C20 1.378(2) . ?
C17 C18 1.399(2) . ?
C12 C13 1.517(2) . ?
C19 C18 1.379(2) . ?
C19 C20 1.393(2) . ?
C7 C6 1.408(2) . ?
C6 C5 1.372(3) . ?
C14 C15 1.526(2) . ?
C15 O5 1.4388(18) . ?
C15 C16 1.518(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
O1 Cu1 N1 91.71(5) . . ?
O1 Cu1 O2 94.31(5) . . ?
N1 Cu1 O2 155.68(5) . . ?
O1 Cu1 N2 168.27(5) . . ?
N1 Cu1 N2 84.10(6) . . ?
O2 Cu1 N2 93.98(5) . . ?
C1 O1 Cu1 124.65(9) . . ?
C14 N2 C13 113.74(12) . . ?
C14 N2 Cu1 112.84(10) . . ?
C13 N2 Cu1 106.20(9) . . ?
C23 O2 Cu1 107.70(9) . . ?
C11 N1 C12 120.26(13) . . ?
C11 N1 Cu1 124.74(11) . . ?
C12 N1 Cu1 113.98(9) . . ?
N1 C11 C10 125.23(14) . . ?
O3 C23 O2 122.18(14) . . ?
O3 C23 C17 121.49(13) . . ?
O2 C23 C17 116.32(12) . . ?
C3 C2 C1 121.57(14) . . ?
C8 C9 C4 117.24(14) . . ?
C8 C9 C10 123.37(14) . . ?
C4 C9 C10 119.40(14) . . ?
C5 C4 C9 120.15(15) . . ?
C5 C4 C3 120.92(15) . . ?
C9 C4 C3 118.93(14) . . ?
C2 C3 C4 121.66(14) . . ?
O1 C1 C10 125.14(14) . . ?
O1 C1 C2 116.52(13) . . ?
C10 C1 C2 118.33(14) . . ?
C7 C8 C9 121.59(15) . . ?
O4 C22 C21 117.57(14) . . ?
O4 C22 C17 122.49(14) . . ?
C21 C22 C17 119.94(14) . . ?
C20 C21 C22 120.31(14) . . ?
C18 C17 C22 118.33(14) . . ?
C18 C17 C23 119.64(13) . . ?
C22 C17 C23 122.02(13) . . ?
N1 C12 C13 107.36(12) . . ?
C18 C19 C20 119.12(15) . . ?
C1 C10 C11 121.35(14) . . ?
C1 C10 C9 119.65(15) . . ?
C11 C10 C9 118.90(14) . . ?
C21 C20 C19 120.59(14) . . ?
C8 C7 C6 120.88(15) . . ?
C5 C6 C7 118.93(16) . . ?
C6 C5 C4 121.17(17) . . ?
N2 C13 C12 107.77(12) . . ?
C19 C18 C17 121.71(14) . . ?
N2 C14 C15 111.76(12) . . ?
O5 C15 C16 111.81(12) . . ?
O5 C15 C14 106.86(12) . . ?
C16 C15 C14 109.88(13) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.045


