# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
#######################################################################
# 
#  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
#  of the CCDC or of third parties, and may not be copied or further
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cu N2 O4'
_chemical_formula_sum            'C20 H16 Cu N2 O4'
_chemical_formula_weight         411.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_hall  '-P 2ybc'

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                   12.6160(4)
_cell_length_b                   23.0976(8)
_cell_length_c                   7.0880(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.372(2)
_cell_angle_gamma                90.00
_cell_volume                     2017.47(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    32430
_cell_measurement_theta_min      1.65
_cell_measurement_theta_max      27.22

_exptl_crystal_description       'Rod shape'
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    1.108
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.758
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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 SMART APEX-II CCD'
_diffrn_measurement_method       Multi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32430
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         27.22
_reflns_number_total             4496
_reflns_number_gt                3037
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART APEX II CCD'
_computing_cell_refinement       'BRUKER SMART APEX II CCD'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    MERCURY-3.1
_computing_publication_material  'SHELXS-97 (Sheldrick, 2008)'

_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)+(0.1544P)²+1.3694P] 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       0.0014(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4496
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2677
_refine_ls_wR_factor_gt          0.2450
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.01336(6) 0.50614(3) 0.25371(8) 0.0635(3) Uani 1 1 d . . .
O4 O 0.1613(3) 0.52315(19) 0.2597(6) 0.0747(11) Uani 1 1 d . . .
C9 C 0.1133(5) 0.4011(3) 0.1597(7) 0.0676(14) Uani 1 1 d . . .
H1 H 0.1078 0.3621 0.1263 0.081 Uiso 1 1 calc R . .
C5 C 0.3034(5) 0.3928(3) 0.1525(8) 0.0772(16) Uani 1 1 d . . .
H3 H 0.2887 0.3544 0.1167 0.093 Uiso 1 1 calc R . .
C12 C -0.2067(5) 0.5198(3) 0.2969(7) 0.0674(14) Uani 1 1 d . . .
H2 H -0.2740 0.5037 0.2998 0.081 Uiso 1 1 calc R . .
N1 N -0.1320(4) 0.4843(2) 0.2711(6) 0.0647(11) Uani 1 1 d . . .
N2 N 0.0272(4) 0.42642(19) 0.1796(6) 0.0613(10) Uani 1 1 d . . .
C6 C 0.4075(5) 0.4127(3) 0.1715(8) 0.0859(18) Uani 1 1 d . . .
C1 C 0.3681(7) 0.5694(4) 0.3097(15) 0.110(2) Uani 1 1 d . . .
C3 C 0.2365(5) 0.4858(3) 0.2316(7) 0.0719(16) Uani 1 1 d . . .
C16 C -0.1896(7) 0.6991(3) 0.3657(9) 0.093(2) Uani 1 1 d . . .
H0VR H -0.1873 0.7392 0.3787 0.112 Uiso 1 1 calc R . .
C14 C -0.0988(5) 0.6101(2) 0.3195(7) 0.0678(14) Uani 1 1 d . . .
O2 O 0.3160(9) 0.5901(4) 0.4319(15) 0.108(3) Uani 0.50 1 d P . .
C18 C -0.2870(5) 0.6117(3) 0.3499(8) 0.0772(16) Uani 1 1 d . . .
H2IG H -0.3502 0.5915 0.3540 0.093 Uiso 1 1 calc R . .
C15 C -0.1011(7) 0.6712(3) 0.3419(8) 0.0867(19) Uani 1 1 d . . .
C8 C 0.5012(6) 0.3759(4) 0.1388(13) 0.121(3) Uani 1 1 d . . .
H3Q1 H 0.5262 0.3903 0.0289 0.181 Uiso 1 1 calc R . .
H3Q2 H 0.4776 0.3365 0.1158 0.181 Uiso 1 1 calc R . .
H3Q3 H 0.5593 0.3776 0.2511 0.181 Uiso 1 1 calc R . .
C7 C 0.4258(6) 0.4712(4) 0.2230(9) 0.091(2) Uani 1 1 d . . .
H3TR H 0.4958 0.4859 0.2387 0.110 Uiso 1 1 calc R . .
C2 C 0.3446(6) 0.5074(3) 0.2511(9) 0.0853(19) Uani 1 1 d . . .
O3 O 0.0030(15) 0.7573(5) 0.342(3) 0.163(6) Uani 0.50 1 d P . .
C19 C -0.3870(8) 0.7033(4) 0.4048(13) 0.125(3) Uani 1 1 d . . .
H4L1 H -0.3821 0.7430 0.3678 0.188 Uiso 1 1 calc R . .
H4L2 H -0.3899 0.7013 0.5389 0.188 Uiso 1 1 calc R . .
H4L3 H -0.4514 0.6862 0.3282 0.188 Uiso 1 1 calc R . .
C20 C 0.0071(8) 0.7030(4) 0.3228(18) 0.134(4) Uani 1 1 d . . .
C13 C -0.1968(5) 0.5807(3) 0.3213(7) 0.0673(14) Uani 1 1 d . . .
C11 C -0.1496(5) 0.4223(3) 0.2607(8) 0.0716(14) Uani 1 1 d . . .
H7L1 H -0.2250 0.4140 0.2035 0.086 Uiso 1 1 calc R . .
H7L2 H -0.1327 0.4057 0.3895 0.086 Uiso 1 1 calc R . .
C10 C -0.0769(5) 0.3956(2) 0.1383(8) 0.0732(14) Uani 1 1 d . . .
H8I1 H -0.0655 0.3549 0.1691 0.088 Uiso 1 1 calc R . .
H8I2 H -0.1107 0.3991 0.0024 0.088 Uiso 1 1 calc R . .
C4 C 0.2189(5) 0.4274(3) 0.1841(7) 0.0678(14) Uani 1 1 d . . .
C17 C -0.2866(6) 0.6700(3) 0.3720(8) 0.0896(19) Uani 1 1 d . . .
O1 O -0.0082(3) 0.58538(18) 0.3014(6) 0.0735(10) Uani 1 1 d . . .
O2A O 0.3149(12) 0.6066(6) 0.209(2) 0.153(6) Uani 0.50 1 d P . .
O3A O 0.0656(11) 0.7084(7) 0.485(2) 0.151(5) Uani 0.50 1 d P . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.892(4) . ?
Cu1 O4 1.899(4) . ?
Cu1 N1 1.931(5) . ?
Cu1 N2 1.933(5) . ?
O4 C3 1.329(8) . ?
C9 N2 1.268(7) . ?
C9 C4 1.439(8) . ?
C9 H1 0.9300 . ?
C5 C6 1.371(9) . ?
C5 C4 1.388(9) . ?
C5 H3 0.9300 . ?
C12 N1 1.291(8) . ?
C12 C13 1.420(8) . ?
C12 H2 0.9300 . ?
N1 C11 1.450(7) . ?
N2 C10 1.467(7) . ?
C6 C7 1.406(10) . ?
C6 C8 1.513(10) . ?
C1 O2A 1.221(15) . ?
C1 O2 1.287(12) . ?
C1 C2 1.502(11) . ?
C3 C4 1.397(8) . ?
C3 C2 1.430(10) . ?
C16 C15 1.331(10) . ?
C16 C17 1.405(10) . ?
C16 H0VR 0.9300 . ?
C14 O1 1.308(7) . ?
C14 C13 1.414(8) . ?
C14 C15 1.422(8) . ?
O2 O2A 1.619(19) . ?
C18 C17 1.354(10) . ?
C18 C13 1.395(8) . ?
C18 H2IG 0.9300 . ?
C15 C20 1.580(12) . ?
C8 H3Q1 0.9600 . ?
C8 H3Q2 0.9600 . ?
C8 H3Q3 0.9600 . ?
C7 C2 1.370(10) . ?
C7 H3TR 0.9300 . ?
O3 C20 1.264(13) . ?
O3 O3A 1.61(2) . ?
C19 C17 1.541(10) . ?
C19 H4L1 0.9600 . ?
C19 H4L2 0.9600 . ?
C19 H4L3 0.9600 . ?
C20 O3A 1.232(16) . ?
C11 C10 1.521(8) . ?
C11 H7L1 0.9700 . ?
C11 H7L2 0.9700 . ?
C10 H8I1 0.9700 . ?
C10 H8I2 0.9700 . ?

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 88.51(19) . . ?
O1 Cu1 N1 93.79(19) . . ?
O4 Cu1 N1 174.21(17) . . ?
O1 Cu1 N2 174.36(16) . . ?
O4 Cu1 N2 93.32(19) . . ?
N1 Cu1 N2 84.9(2) . . ?
C3 O4 Cu1 126.3(4) . . ?
N2 C9 C4 125.8(6) . . ?
N2 C9 H1 117.1 . . ?
C4 C9 H1 117.1 . . ?
C6 C5 C4 123.0(7) . . ?
C6 C5 H3 118.5 . . ?
C4 C5 H3 118.5 . . ?
N1 C12 C13 126.7(6) . . ?
N1 C12 H2 116.6 . . ?
C13 C12 H2 116.6 . . ?
C12 N1 C11 121.7(5) . . ?
C12 N1 Cu1 125.2(4) . . ?
C11 N1 Cu1 113.1(4) . . ?
C9 N2 C10 120.4(5) . . ?
C9 N2 Cu1 126.8(4) . . ?
C10 N2 Cu1 112.8(4) . . ?
C5 C6 C7 116.6(7) . . ?
C5 C6 C8 124.1(7) . . ?
C7 C6 C8 119.3(7) . . ?
O2A C1 O2 80.4(12) . . ?
O2A C1 C2 117.3(10) . . ?
O2 C1 C2 116.2(8) . . ?
O4 C3 C4 125.6(6) . . ?
O4 C3 C2 117.1(6) . . ?
C4 C3 C2 117.4(6) . . ?
C15 C16 C17 122.2(7) . . ?
C15 C16 H0VR 118.9 . . ?
C17 C16 H0VR 118.9 . . ?
O1 C14 C13 125.1(5) . . ?
O1 C14 C15 119.0(6) . . ?
C13 C14 C15 115.9(6) . . ?
C1 O2 O2A 48.0(7) . . ?
C17 C18 C13 122.9(7) . . ?
C17 C18 H2IG 118.5 . . ?
C13 C18 H2IG 118.5 . . ?
C16 C15 C14 122.2(7) . . ?
C16 C15 C20 123.4(7) . . ?
C14 C15 C20 114.4(7) . . ?
C6 C8 H3Q1 109.5 . . ?
C6 C8 H3Q2 109.5 . . ?
H3Q1 C8 H3Q2 109.5 . . ?
C6 C8 H3Q3 109.5 . . ?
H3Q1 C8 H3Q3 109.5 . . ?
H3Q2 C8 H3Q3 109.5 . . ?
C2 C7 C6 122.6(7) . . ?
C2 C7 H3TR 118.7 . . ?
C6 C7 H3TR 118.7 . . ?
C7 C2 C3 120.0(7) . . ?
C7 C2 C1 120.8(7) . . ?
C3 C2 C1 119.2(7) . . ?
C20 O3 O3A 49.0(8) . . ?
C17 C19 H4L1 109.5 . . ?
C17 C19 H4L2 109.5 . . ?
H4L1 C19 H4L2 109.5 . . ?
C17 C19 H4L3 109.5 . . ?
H4L1 C19 H4L3 109.5 . . ?
H4L2 C19 H4L3 109.5 . . ?
O3A C20 O3 80.2(13) . . ?
O3A C20 C15 108.9(11) . . ?
O3 C20 C15 113.3(12) . . ?
C18 C13 C14 119.8(6) . . ?
C18 C13 C12 118.3(6) . . ?
C14 C13 C12 121.9(6) . . ?
N1 C11 C10 108.9(4) . . ?
N1 C11 H7L1 109.9 . . ?
C10 C11 H7L1 109.9 . . ?
N1 C11 H7L2 109.9 . . ?
C10 C11 H7L2 109.9 . . ?
H7L1 C11 H7L2 108.3 . . ?
N2 C10 C11 108.3(4) . . ?
N2 C10 H8I1 110.0 . . ?
C11 C10 H8I1 110.0 . . ?
N2 C10 H8I2 110.0 . . ?
C11 C10 H8I2 110.0 . . ?
H8I1 C10 H8I2 108.4 . . ?
C5 C4 C3 120.4(6) . . ?
C5 C4 C9 117.5(6) . . ?
C3 C4 C9 122.1(6) . . ?
C18 C17 C16 117.0(7) . . ?
C18 C17 C19 122.0(8) . . ?
C16 C17 C19 121.0(7) . . ?
C14 O1 Cu1 127.0(4) . . ?
C1 O2A O2 51.6(9) . . ?
C20 O3A O3 50.8(10) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.22
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.132
_database_code_depnum_ccdc_archive 'CCDC 942788'
