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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_r-3c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 Cu N2 O5'
_chemical_formula_sum            'C14 H8 Cu N2 O5'
_chemical_formula_weight         347.77

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

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   'R -3 c '
_symmetry_space_group_name_Hall  '-R 3 2"c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'-x, -x+y, -z+1/2'
'x-y, -y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'x, x-y, z-1/2'
'-x+y, y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'

_cell_length_a                   18.4310(17)
_cell_length_b                   18.4310(17)
_cell_length_c                   69.911(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     20567(7)
_cell_formula_units_Z            36
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6607
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      22.12

_exptl_crystal_description       block
_exptl_crystal_colour            Aquamarine
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.011
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6300
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_process_details   'SADABA, (Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            36383
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -83
_diffrn_reflns_limit_l_max       80
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4039
_reflns_number_gt                3296
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1061P)²+76.8451P] 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         4040
_refine_ls_number_parameters     199
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1905
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.209
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 115 43 ' '
2 0.000 0.000 0.088 34 3 ' '
3 0.000 0.000 0.250 430 75 ' '
4 0.000 0.000 0.412 34 2 ' '
5 0.000 0.000 0.500 115 43 ' '
6 0.000 0.000 0.588 34 3 ' '
7 0.000 0.000 0.750 430 75 ' '
8 0.000 0.000 0.912 34 2 ' '
9 0.333 0.667 0.417 430 75 ' '
10 0.333 0.667 0.917 430 75 ' '
11 0.333 0.667 0.167 115 43 ' '
12 0.333 0.667 0.667 115 43 ' '
13 0.333 0.667 0.255 35 3 ' '
14 0.333 0.667 0.755 35 3 ' '
15 0.333 0.667 0.079 35 2 ' '
16 0.333 0.667 0.579 35 2 ' '
17 0.667 0.333 0.083 430 75 ' '
18 0.667 0.333 0.583 430 75 ' '
19 0.667 0.333 0.333 115 43 ' '
20 0.667 0.333 0.833 115 43 ' '
21 0.667 0.333 0.421 35 3 ' '
22 0.667 0.333 0.921 35 3 ' '
23 0.667 0.333 0.245 35 2 ' '
24 0.667 0.333 0.745 35 2 ' '

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 0.28408(3) 1.12300(3) 0.901319(7) 0.0322(2) Uani 1 1 d . . .
N1 N 0.2014(3) 0.7443(3) 1.04200(5) 0.0416(9) Uani 1 1 d . . .
O1 O 0.3009(2) 1.0563(2) 0.94107(5) 0.0490(9) Uani 1 1 d . . .
O2 O 0.2213(2) 1.0182(2) 0.91489(4) 0.0464(9) Uani 1 1 d . . .
O3 O -0.0563(2) 0.7751(2) 0.91626(5) 0.0593(10) Uani 1 1 d . . .
O4 O -0.0991(2) 0.6912(2) 0.94197(5) 0.0590(11) Uani 1 1 d . . .
C1 C 0.2384(3) 1.0063(3) 0.93164(7) 0.0393(10) Uani 1 1 d . . .
C2 C 0.1780(3) 0.9242(3) 0.94058(7) 0.0461(12) Uani 1 1 d . . .
C3 C 0.0995(3) 0.8778(3) 0.93251(7) 0.0477(12) Uani 1 1 d . . .
H3 H 0.0860 0.8966 0.9214 0.057 Uiso 1 1 calc R . .
C4 C 0.0401(3) 0.8024(3) 0.94104(8) 0.0528(14) Uani 1 1 d . . .
C5 C 0.0607(4) 0.7748(4) 0.95736(9) 0.0700(19) Uani 1 1 d . . .
H5 H 0.0211 0.7250 0.9631 0.084 Uiso 1 1 calc R . .
C6 C 0.1402(4) 0.8209(4) 0.96535(10) 0.0699(19) Uani 1 1 d . . .
C7 C 0.1997(4) 0.8965(4) 0.95687(8) 0.0584(15) Uani 1 1 d . . .
H7 H 0.2531 0.9275 0.9621 0.070 Uiso 1 1 calc R . .
C8 C -0.0442(3) 0.7531(3) 0.93225(7) 0.0484(12) Uani 1 1 d . . .
C9 C 0.2022(6) 0.7471(7) 1.00804(9) 0.109(4) Uani 1 1 d D . .
C10 C 0.1993(7) 0.6704(8) 1.00780(10) 0.127(4) Uani 1 1 d . A .
H10 H 0.1982 0.6452 0.9962 0.152 Uiso 1 1 calc R . .
C11 C 0.1982(6) 0.6323(5) 1.02452(11) 0.094(3) Uani 1 1 d . . .
H11 H 0.1951 0.5804 1.0245 0.112 Uiso 1 1 calc R A .
C12 C 0.2017(4) 0.6722(4) 1.04136(7) 0.0573(15) Uani 1 1 d . A .
H12 H 0.2043 0.6479 1.0528 0.069 Uiso 1 1 calc R . .
C13 C 0.2028(5) 0.7798(5) 1.02561(8) 0.078(2) Uani 1 1 d . A .
H13 H 0.2043 0.8310 1.0260 0.093 Uiso 1 1 calc R . .
C14 C 0.2205(6) 0.8103(7) 0.99175(15) 0.120(2) Uani 1 1 d DU A 2
O5 O 0.2715(5) 0.8930(5) 0.99203(10) 0.133(2) Uani 1 1 d DU A 2
N2 N 0.1565(4) 0.7919(4) 0.98247(11) 0.111(3) Uani 1 1 d DU A 2
H2' H 0.1119 0.7525 0.9877 0.133 Uiso 1 1 calc R 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 O2 1.932(3) . ?
Cu1 O4 1.936(4) 10_466 ?
Cu1 O3 1.975(4) 2_675 ?
Cu1 O1 2.004(3) 11_556 ?
Cu1 N1 2.176(4) 30_455 ?
Cu1 Cu1 2.6603(10) 11_556 ?
N1 C13 1.313(7) . ?
N1 C12 1.333(6) . ?
N1 Cu1 2.176(4) 36_445 ?
O1 C1 1.245(6) . ?
O1 Cu1 2.004(3) 11_556 ?
O2 C1 1.260(5) . ?
O3 C8 1.247(6) . ?
O3 Cu1 1.975(4) 3_465 ?
O4 C8 1.278(6) . ?
O4 Cu1 1.936(3) 10_356 ?
C1 C2 1.495(7) . ?
C2 C3 1.380(7) . ?
C2 C7 1.387(7) . ?
C3 C4 1.401(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(7) . ?
C4 C8 1.486(7) . ?
C5 C6 1.392(8) . ?
C5 H5 0.9300 . ?
C6 N2 1.403(9) . ?
C6 C7 1.403(8) . ?
C7 H7 0.9300 . ?
C9 C13 1.366(9) . ?
C9 C10 1.388(13) . ?
C9 C14 1.541(11) . ?
C10 C11 1.358(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N2 1.235(10) . ?
C14 O5 1.332(10) . ?
N2 H2' 0.8600 . ?

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
O2 Cu1 O4 170.85(14) . 10_466 ?
O2 Cu1 O3 89.02(18) . 2_675 ?
O4 Cu1 O3 89.1(2) 10_466 2_675 ?
O2 Cu1 O1 90.54(16) . 11_556 ?
O4 Cu1 O1 88.81(19) 10_466 11_556 ?
O3 Cu1 O1 164.25(14) 2_675 11_556 ?
O2 Cu1 N1 94.52(14) . 30_455 ?
O4 Cu1 N1 94.63(15) 10_466 30_455 ?
O3 Cu1 N1 103.20(15) 2_675 30_455 ?
O1 Cu1 N1 92.53(14) 11_556 30_455 ?
O2 Cu1 Cu1 84.86(10) . 11_556 ?
O4 Cu1 Cu1 86.01(11) 10_466 11_556 ?
O3 Cu1 Cu1 81.72(10) 2_675 11_556 ?
O1 Cu1 Cu1 82.56(10) 11_556 11_556 ?
N1 Cu1 Cu1 175.04(11) 30_455 11_556 ?
C13 N1 C12 117.3(5) . . ?
C13 N1 Cu1 119.0(4) . 36_445 ?
C12 N1 Cu1 122.4(3) . 36_445 ?
C1 O1 Cu1 123.1(3) . 11_556 ?
C1 O2 Cu1 123.6(3) . . ?
C8 O3 Cu1 125.4(3) . 3_465 ?
C8 O4 Cu1 121.6(3) . 10_356 ?
O1 C1 O2 125.6(4) . . ?
O1 C1 C2 118.2(4) . . ?
O2 C1 C2 116.1(4) . . ?
C3 C2 C7 120.9(5) . . ?
C3 C2 C1 118.4(4) . . ?
C7 C2 C1 120.7(4) . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 C8 120.9(5) . . ?
C3 C4 C8 119.3(4) . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 N2 118.1(5) . . ?
C5 C6 C7 119.9(5) . . ?
N2 C6 C7 121.9(6) . . ?
C2 C7 C6 119.1(5) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
O3 C8 O4 125.2(5) . . ?
O3 C8 C4 118.3(4) . . ?
O4 C8 C4 116.4(4) . . ?
C13 C9 C10 116.6(6) . . ?
C13 C9 C14 112.4(8) . . ?
C10 C9 C14 130.0(7) . . ?
C11 C10 C9 119.9(6) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 118.5(7) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
N1 C12 C11 122.7(5) . . ?
N1 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N1 C13 C9 124.8(6) . . ?
N1 C13 H13 117.6 . . ?
C9 C13 H13 117.6 . . ?
N2 C14 O5 110.6(9) . . ?
N2 C14 C9 111.3(8) . . ?
O5 C14 C9 128.1(9) . . ?
C14 N2 C6 134.5(7) . . ?
C14 N2 H2' 112.8 . . ?
C6 N2 H2' 112.8 . . ?

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
O4 Cu1 O2 C1 0.1(13) 10_466 . . . ?
O3 Cu1 O2 C1 -78.4(4) 2_675 . . . ?
O1 Cu1 O2 C1 85.9(4) 11_556 . . . ?
N1 Cu1 O2 C1 178.5(4) 30_455 . . . ?
Cu1 Cu1 O2 C1 3.4(4) 11_556 . . . ?
Cu1 O1 C1 O2 5.8(7) 11_556 . . . ?
Cu1 O1 C1 C2 -174.9(3) 11_556 . . . ?
Cu1 O2 C1 O1 -6.5(7) . . . . ?
Cu1 O2 C1 C2 174.1(3) . . . . ?
O1 C1 C2 C3 164.1(5) . . . . ?
O2 C1 C2 C3 -16.5(7) . . . . ?
O1 C1 C2 C7 -14.3(8) . . . . ?
O2 C1 C2 C7 165.1(5) . . . . ?
C7 C2 C3 C4 1.2(9) . . . . ?
C1 C2 C3 C4 -177.2(5) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
C2 C3 C4 C8 179.8(5) . . . . ?
C3 C4 C5 C6 -0.6(11) . . . . ?
C8 C4 C5 C6 179.2(7) . . . . ?
C4 C5 C6 N2 177.1(7) . . . . ?
C4 C5 C6 C7 0.6(12) . . . . ?
C3 C2 C7 C6 -1.2(10) . . . . ?
C1 C2 C7 C6 177.2(6) . . . . ?
C5 C6 C7 C2 0.3(11) . . . . ?
N2 C6 C7 C2 -176.1(7) . . . . ?
Cu1 O3 C8 O4 -3.9(9) 3_465 . . . ?
Cu1 O3 C8 C4 176.7(4) 3_465 . . . ?
Cu1 O4 C8 O3 3.6(8) 10_356 . . . ?
Cu1 O4 C8 C4 -176.9(4) 10_356 . . . ?
C5 C4 C8 O3 -171.1(6) . . . . ?
C3 C4 C8 O3 8.7(9) . . . . ?
C5 C4 C8 O4 9.4(9) . . . . ?
C3 C4 C8 O4 -170.8(5) . . . . ?
C13 C9 C10 C11 -0.7(16) . . . . ?
C14 C9 C10 C11 167.1(10) . . . . ?
C9 C10 C11 C12 -1.3(16) . . . . ?
C13 N1 C12 C11 -4.1(10) . . . . ?
Cu1 N1 C12 C11 162.6(6) 36_445 . . . ?
C10 C11 C12 N1 3.8(13) . . . . ?
C12 N1 C13 C9 1.9(11) . . . . ?
Cu1 N1 C13 C9 -165.2(7) 36_445 . . . ?
C10 C9 C13 N1 0.4(14) . . . . ?
C14 C9 C13 N1 -169.5(7) . . . . ?
C13 C9 C14 N2 -107.0(11) . . . . ?
C10 C9 C14 N2 84.9(14) . . . . ?
C13 C9 C14 O5 34.7(14) . . . . ?
C10 C9 C14 O5 -133.4(13) . . . . ?
O5 C14 N2 C6 40.7(18) . . . . ?
C9 C14 N2 C6 -170.7(10) . . . . ?
C5 C6 N2 C14 168.8(12) . . . . ?
C7 C6 N2 C14 -14.8(18) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.008
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.098
_database_code_depnum_ccdc_archive 'CCDC 981374'
