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# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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data_s_cu_1_a
_audit_creation_date             2014-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H15 Cu N3 O7'
_chemical_formula_sum            'C22 H15 Cu N3 O7'
_chemical_formula_weight         496.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8172(2)
_cell_length_b                   17.6565(5)
_cell_length_c                   17.2653(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.966(2)
_cell_angle_gamma                90
_cell_volume                     2058.13(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3707
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.58
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0809 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.9099.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16683
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_min         1.658
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3016
_reflns_number_total             4761
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.621
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4761
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²+1.3073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1685
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N3-H3A
 0.95 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.67340(7) 0.67845(3) 0.43978(3) 0.03702(19) Uani 1 1 d . . . . .
O1 O 0.5612(5) 0.78105(18) 0.4479(2) 0.0508(8) Uani 1 1 d . . . . .
O2 O 0.7995(5) 0.8523(2) 0.4136(3) 0.0739(11) Uani 1 1 d . . . . .
O3 O 0.2931(5) 0.8914(2) 0.4245(2) 0.0646(10) Uani 1 1 d . . . . .
O4 O 0.5642(4) 0.67348(16) 0.32716(18) 0.0449(7) Uani 1 1 d . . . . .
O5 O 0.2755(5) 0.63504(19) 0.36174(19) 0.0543(9) Uani 1 1 d . . . . .
O6 O 0.4093(5) 0.66885(17) 0.17329(18) 0.0466(8) Uani 1 1 d . . . . .
O7 O 0.9780(5) 0.71734(19) 0.4233(2) 0.0644(10) Uani 1 1 d . . . . .
N1 N 0.7201(5) 0.66550(19) 0.5603(2) 0.0372(8) Uani 1 1 d . . . . .
N2 N 0.7257(5) 0.56789(19) 0.44643(19) 0.0343(8) Uani 1 1 d . . . . .
N3 N 0.7576(5) 0.46454(19) 0.5211(2) 0.0360(8) Uani 1 1 d D . . . .
H3A H 0.735(10) 0.437(4) 0.567(3) 0.12(3) Uiso 1 1 d D . . . .
C1 C 0.7238(6) 0.7181(3) 0.6157(3) 0.0446(11) Uani 1 1 d . . . . .
H1 H 0.7092 0.7685 0.6003 0.054 Uiso 1 1 calc R . . . .
C2 C 0.7475(7) 0.7024(3) 0.6938(3) 0.0504(12) Uani 1 1 d . . . . .
H2 H 0.7508 0.7412 0.7304 0.060 Uiso 1 1 calc R . . . .
C3 C 0.7663(7) 0.6285(3) 0.7172(3) 0.0533(13) Uani 1 1 d . . . . .
H3 H 0.7798 0.6164 0.7701 0.064 Uiso 1 1 calc R . . . .
C4 C 0.7652(6) 0.5714(3) 0.6612(3) 0.0415(10) Uani 1 1 d . . . . .
H4 H 0.7790 0.5207 0.6755 0.050 Uiso 1 1 calc R . . . .
C5 C 0.7429(5) 0.5934(2) 0.5840(2) 0.0347(9) Uani 1 1 d . . . . .
C6 C 0.7420(5) 0.5412(2) 0.5184(2) 0.0291(8) Uani 1 1 d . . . . .
C7 C 0.7517(5) 0.4395(2) 0.4451(2) 0.0333(9) Uani 1 1 d . . . . .
C8 C 0.7609(6) 0.3678(2) 0.4143(3) 0.0434(11) Uani 1 1 d . . . . .
H8 H 0.7728 0.3250 0.4459 0.052 Uiso 1 1 calc R . . . .
C9 C 0.7518(7) 0.3627(3) 0.3354(3) 0.0503(12) Uani 1 1 d . . . . .
H9 H 0.7589 0.3153 0.3124 0.060 Uiso 1 1 calc R . . . .
C10 C 0.7322(6) 0.4268(3) 0.2882(3) 0.0473(11) Uani 1 1 d . . . . .
H10 H 0.7250 0.4206 0.2344 0.057 Uiso 1 1 calc R . . . .
C11 C 0.7229(6) 0.4987(3) 0.3173(3) 0.0405(10) Uani 1 1 d . . . . .
H11 H 0.7122 0.5410 0.2849 0.049 Uiso 1 1 calc R . . . .
C12 C 0.7304(5) 0.5051(2) 0.3977(2) 0.0350(9) Uani 1 1 d . . . . .
C13 C 0.3846(7) 0.6528(2) 0.3121(3) 0.0403(10) Uani 1 1 d . . . . .
C14 C 0.2953(6) 0.6496(2) 0.2297(3) 0.0408(10) Uani 1 1 d . . . . .
C15 C 0.1130(7) 0.6328(3) 0.1947(3) 0.0566(13) Uani 1 1 d . . . . .
H15 H 0.0064 0.6180 0.2194 0.068 Uiso 1 1 calc R . . . .
C16 C 0.1117(8) 0.6417(3) 0.1127(3) 0.0619(14) Uani 1 1 d . . . . .
H16 H 0.0054 0.6338 0.0736 0.074 Uiso 1 1 calc R . . . .
C17 C 0.2931(8) 0.6634(3) 0.1036(3) 0.0526(12) Uani 1 1 d . . . . .
H17 H 0.3347 0.6736 0.0556 0.063 Uiso 1 1 calc R . . . .
C18 C 0.6283(7) 0.8384(3) 0.4280(3) 0.0464(11) Uani 1 1 d . . . . .
C19 C 0.4903(7) 0.9042(3) 0.4173(3) 0.0489(11) Uani 1 1 d . . . . .
C20 C 0.5173(8) 0.9772(3) 0.4008(3) 0.0574(13) Uani 1 1 d . . . . .
H20 H 0.6350 1.0000 0.3917 0.069 Uiso 1 1 calc R . . . .
C21 C 0.3295(9) 1.0133(3) 0.4001(3) 0.0722(17) Uani 1 1 d . . . . .
H21 H 0.3029 1.0645 0.3913 0.087 Uiso 1 1 calc R . . . .
C22 C 0.1990(9) 0.9606(3) 0.4141(3) 0.0643(15) Uani 1 1 d . . . . .
H22 H 0.0654 0.9691 0.4166 0.077 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 1.979(3) . ?
Cu1 O4 1.985(3) . ?
Cu1 O7 2.243(3) . ?
Cu1 N1 2.073(4) . ?
Cu1 N2 1.985(3) . ?
O1 C18 1.182(6) . ?
O2 C18 1.251(6) . ?
O3 C19 1.386(6) . ?
O3 C22 1.379(6) . ?
O4 C13 1.270(5) . ?
O5 C13 1.249(5) . ?
O6 C14 1.370(5) . ?
O6 C17 1.350(5) . ?
N1 C1 1.332(6) . ?
N1 C5 1.340(5) . ?
N2 C6 1.319(5) . ?
N2 C12 1.395(5) . ?
N3 H3A 0.96(2) . ?
N3 C6 1.358(5) . ?
N3 C7 1.380(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.364(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(6) . ?
C5 C6 1.459(6) . ?
C7 C8 1.378(6) . ?
C7 C12 1.414(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.358(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(6) . ?
C13 C14 1.470(6) . ?
C14 C15 1.338(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.422(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.325(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.490(7) . ?
C19 C20 1.339(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.428(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.333(8) . ?
C22 H22 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 O4 90.80(13) . . ?
O1 Cu1 O7 95.88(13) . . ?
O1 Cu1 N1 92.10(13) . . ?
O1 Cu1 N2 164.64(13) . . ?
O4 Cu1 O7 96.75(14) . . ?
O4 Cu1 N1 164.27(13) . . ?
N1 Cu1 O7 98.33(14) . . ?
N2 Cu1 O4 93.05(13) . . ?
N2 Cu1 O7 98.41(13) . . ?
N2 Cu1 N1 80.33(13) . . ?
C18 O1 Cu1 126.5(3) . . ?
C22 O3 C19 106.5(4) . . ?
C13 O4 Cu1 115.7(3) . . ?
C17 O6 C14 107.2(4) . . ?
C1 N1 Cu1 129.0(3) . . ?
C1 N1 C5 117.0(4) . . ?
C5 N1 Cu1 114.0(3) . . ?
C6 N2 Cu1 113.4(3) . . ?
C6 N2 C12 106.1(3) . . ?
C12 N2 Cu1 140.0(3) . . ?
C6 N3 H3A 121(4) . . ?
C6 N3 C7 107.2(3) . . ?
C7 N3 H3A 129(4) . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.8(4) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(5) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.2(4) . . ?
C5 C4 H4 121.4 . . ?
N1 C5 C4 123.8(4) . . ?
N1 C5 C6 112.0(4) . . ?
C4 C5 C6 124.2(4) . . ?
N2 C6 N3 112.6(4) . . ?
N2 C6 C5 119.8(3) . . ?
N3 C6 C5 127.6(4) . . ?
N3 C7 C12 105.9(4) . . ?
C8 C7 N3 131.8(4) . . ?
C8 C7 C12 122.3(4) . . ?
C7 C8 H8 121.6 . . ?
C9 C8 C7 116.8(4) . . ?
C9 C8 H8 121.6 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(4) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 118.5 . . ?
C11 C10 C9 123.0(4) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 H11 121.8 . . ?
C10 C11 C12 116.4(4) . . ?
C12 C11 H11 121.8 . . ?
N2 C12 C7 108.2(3) . . ?
C11 C12 N2 131.8(4) . . ?
C11 C12 C7 120.0(4) . . ?
O4 C13 C14 117.8(4) . . ?
O5 C13 O4 125.5(4) . . ?
O5 C13 C14 116.7(4) . . ?
O6 C14 C13 118.6(4) . . ?
C15 C14 O6 108.5(4) . . ?
C15 C14 C13 132.8(4) . . ?
C14 C15 H15 126.2 . . ?
C14 C15 C16 107.6(4) . . ?
C16 C15 H15 126.2 . . ?
C15 C16 H16 127.1 . . ?
C17 C16 C15 105.9(5) . . ?
C17 C16 H16 127.1 . . ?
O6 C17 H17 124.6 . . ?
C16 C17 O6 110.9(4) . . ?
C16 C17 H17 124.6 . . ?
O1 C18 O2 129.5(5) . . ?
O1 C18 C19 116.2(4) . . ?
O2 C18 C19 114.4(5) . . ?
O3 C19 C18 117.7(4) . . ?
C20 C19 O3 109.8(4) . . ?
C20 C19 C18 132.4(5) . . ?
C19 C20 H20 126.8 . . ?
C19 C20 C21 106.4(5) . . ?
C21 C20 H20 126.8 . . ?
C20 C21 H21 126.1 . . ?
C22 C21 C20 107.9(5) . . ?
C22 C21 H21 126.1 . . ?
O3 C22 H22 125.3 . . ?
C21 C22 O3 109.4(5) . . ?
C21 C22 H22 125.3 . . ?

_database_code_depnum_ccdc_archive 'CCDC 1017813'
