# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_LIFM-11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 Cu N2 O6'
_chemical_formula_weight         363.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'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'
'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'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-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'
'-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'

_cell_length_a                   18.569(3)
_cell_length_b                   18.569(3)
_cell_length_c                   40.907(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     12215(3)
_cell_formula_units_Z            18
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3014
_cell_measurement_theta_min      2.8863
_cell_measurement_theta_max      24.9574

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.890
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3294
_exptl_absorpt_coefficient_mu    1.312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.400236
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDE IP'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3394
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            37403
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         7.01
_diffrn_reflns_theta_max         89.40
_reflns_number_total             6194
_reflns_number_gt                3779
_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)+(0.1775P)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    goem
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6194
_refine_ls_number_parameters     271
_refine_ls_number_restraints     128
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.2652
_refine_ls_wR_factor_gt          0.2375
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      1.012
_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 0.52412(3) 0.04827(3) 0.025927(11) 0.0458(3) Uani 1 1 d . . .
O1 O 0.5630(3) 0.1272(2) 0.06738(8) 0.0975(14) Uani 1 1 d D A .
N1 N 0.5466(4) 0.0940(3) 0.09627(11) 0.1032(19) Uani 1 1 d D . .
C1A C 0.4752(12) 0.0867(15) 0.1082(6) 0.129(6) Uani 0.40 1 d PDU A 1
H1A H 0.4505 0.1099 0.0946 0.155 Uiso 0.40 1 calc PR A 1
C2A C 0.4318(12) 0.0507(12) 0.1371(5) 0.117(4) Uani 0.40 1 d PDU A 1
H2A H 0.3765 0.0376 0.1419 0.140 Uiso 0.40 1 calc PR A 1
C3A C 0.4827(16) 0.0377(16) 0.1571(6) 0.106(5) Uani 0.40 1 d PDU A 1
C4A C 0.5392(18) 0.0177(19) 0.1455(7) 0.121(6) Uani 0.40 1 d PDU A 1
H4A H 0.5550 -0.0165 0.1571 0.146 Uiso 0.40 1 calc PR A 1
C5A C 0.5715(19) 0.0516(16) 0.1151(6) 0.139(7) Uani 0.40 1 d PDU A 1
H5A H 0.6153 0.0442 0.1070 0.167 Uiso 0.40 1 calc PR A 1
C6A C 0.4477(14) -0.0109(11) 0.1891(5) 0.194(8) Uani 0.60 1 d PDU A 1
O2A O 0.3674(15) -0.0573(15) 0.1901(6) 0.339(12) Uani 0.60 1 d PDU A 1
C1B C 0.4791(13) 0.0583(12) 0.1130(4) 0.30(2) Uani 0.60 1 d PD A 2
H1B H 0.4300 0.0572 0.1057 0.359 Uiso 0.60 1 calc PR A 2
C2B C 0.4813(11) 0.0207(14) 0.1428(4) 0.157(8) Uani 0.60 1 d PD A 2
H2B H 0.4307 -0.0168 0.1534 0.188 Uiso 0.60 1 calc PR A 2
C3B C 0.5545(11) 0.0373(11) 0.1565(5) 0.133(7) Uani 0.60 1 d PD A 2
C4B C 0.6218(12) 0.0575(14) 0.1387(3) 0.189(8) Uani 0.60 1 d PD A 2
H4B H 0.6685 0.0536 0.1457 0.227 Uiso 0.60 1 calc PR A 2
C5B C 0.6129(11) 0.0851(10) 0.1086(4) 0.163(8) Uani 0.60 1 d PD A 2
H5B H 0.6580 0.1004 0.0939 0.195 Uiso 0.60 1 calc PR A 2
C6B C 0.5466(11) -0.0084(11) 0.1900(4) 0.175(8) Uani 0.40 1 d PDU A 2
O2B O 0.5901(14) -0.0416(16) 0.1933(4) 0.228(8) Uani 0.40 1 d PDU A 2
C7 C 0.4779(3) -0.0444(4) 0.24388(14) 0.0854(17) Uani 1 1 d . A .
C8 C 0.4042(4) -0.0614(4) 0.25924(13) 0.0865(16) Uani 1 1 d . . .
H8A H 0.3662 -0.0493 0.2485 0.104 Uiso 1 1 calc R . .
C9 C 0.3862(3) -0.0967(3) 0.29070(11) 0.0680(12) Uani 1 1 d . . .
C10 C 0.4437(3) -0.1133(3) 0.30653(10) 0.0642(11) Uani 1 1 d . . .
H10A H 0.4326 -0.1353 0.3281 0.077 Uiso 1 1 calc R . .
C11 C 0.5168(3) -0.0975(3) 0.29073(11) 0.0701(12) Uani 1 1 d . . .
C12 C 0.5348(3) -0.0611(4) 0.25930(13) 0.0875(17) Uani 1 1 d . . .
H12A H 0.5855 -0.0481 0.2487 0.105 Uiso 1 1 calc R . .
C13 C 0.3064(3) -0.1191(3) 0.30676(10) 0.0627(11) Uani 1 1 d . . .
C14 C 0.5746(3) -0.1188(3) 0.30687(10) 0.0637(11) Uani 1 1 d . . .
N2 N 0.4957(3) -0.0104(4) 0.21134(12) 0.1007(17) Uani 1 1 d D . .
H13A H 0.5487 0.0149 0.2059 0.121 Uiso 0.50 1 calc PR A 1
H13B H 0.4661 0.0122 0.2052 0.121 Uiso 0.50 1 d PR A 2
O3 O 0.2555(2) -0.1064(2) 0.29088(8) 0.0767(10) Uani 1 1 d . . .
O4 O 0.2963(2) -0.1477(2) 0.33504(7) 0.0722(9) Uani 1 1 d . . .
O5 O 0.6379(2) -0.1071(2) 0.29074(8) 0.0761(9) Uani 1 1 d . . .
O6 O 0.5559(2) -0.1477(2) 0.33493(8) 0.0729(9) Uani 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 O5 1.971(3) 15_445 ?
Cu1 O4 1.973(3) 8_544 ?
Cu1 O3 1.975(3) 14 ?
Cu1 O6 1.978(3) 9_654 ?
Cu1 O1 2.119(3) . ?
Cu1 Cu1 2.6285(10) 10_655 ?
O1 N1 1.297(6) . ?
N1 C1B 1.282(16) . ?
N1 C5A 1.340(17) . ?
N1 C1A 1.353(16) . ?
N1 C5B 1.416(15) . ?
C1A C2A 1.399(17) . ?
C2A C3A 1.359(18) . ?
C3A C4A 1.362(18) . ?
C3A C6A 1.54(3) . ?
C4A C5A 1.384(19) . ?
C6A O2A 1.297(16) . ?
C6A N2 1.27(2) . ?
C1B C2B 1.418(17) . ?
C2B C3B 1.354(16) . ?
C3B C4B 1.328(16) . ?
C3B C6B 1.58(2) . ?
C4B C5B 1.374(15) . ?
C6B N2 1.272(16) . ?
C6B O2B 1.245(15) . ?
C7 C12 1.392(7) . ?
C7 C8 1.391(7) . ?
C7 N2 1.439(7) . ?
C8 C9 1.406(7) . ?
C9 C10 1.408(6) . ?
C9 C13 1.478(6) . ?
C10 C11 1.396(6) . ?
C11 C12 1.413(7) . ?
C11 C14 1.473(6) . ?
C13 O4 1.247(5) . ?
C13 O3 1.262(5) . ?
C14 O6 1.241(5) . ?
C14 O5 1.267(5) . ?
O3 Cu1 1.975(3) 15_445 ?
O4 Cu1 1.973(3) 6 ?
O5 Cu1 1.971(3) 14 ?
O6 Cu1 1.978(3) 5_545 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Cu1 O4 90.39(16) 15_445 8_544 ?
O5 Cu1 O3 88.64(17) 15_445 14 ?
O4 Cu1 O3 168.63(13) 8_544 14 ?
O5 Cu1 O6 168.63(13) 15_445 9_654 ?
O4 Cu1 O6 88.67(15) 8_544 9_654 ?
O3 Cu1 O6 90.05(16) 14 9_654 ?
O5 Cu1 O1 95.51(15) 15_445 . ?
O4 Cu1 O1 95.33(14) 8_544 . ?
O3 Cu1 O1 96.04(15) 14 . ?
O6 Cu1 O1 95.86(14) 9_654 . ?
O5 Cu1 Cu1 84.72(9) 15_445 10_655 ?
O4 Cu1 Cu1 84.00(9) 8_544 10_655 ?
O3 Cu1 Cu1 84.63(9) 14 10_655 ?
O6 Cu1 Cu1 83.91(9) 9_654 10_655 ?
O1 Cu1 Cu1 179.29(11) . 10_655 ?
N1 O1 Cu1 118.8(3) . . ?
C1B N1 O1 131.8(12) . . ?
C1B N1 C5A 85.7(16) . . ?
O1 N1 C5A 137.5(15) . . ?
C1B N1 C1A 26.1(17) . . ?
O1 N1 C1A 111.1(13) . . ?
C5A N1 C1A 110.0(18) . . ?
C1B N1 C5B 115.6(13) . . ?
O1 N1 C5B 111.7(9) . . ?
C5A N1 C5B 31.7(13) . . ?
C1A N1 C5B 136.6(15) . . ?
N1 C1A C2A 131(2) . . ?
C3A C2A C1A 108(2) . . ?
C4A C3A C2A 122(3) . . ?
C4A C3A C6A 107.1(19) . . ?
C2A C3A C6A 119(2) . . ?
C5A C4A C3A 114(3) . . ?
N1 C5A C4A 126(3) . . ?
O2A C6A N2 124(2) . . ?
O2A C6A C3A 115(2) . . ?
N2 C6A C3A 121.1(19) . . ?
N1 C1B C2B 117(2) . . ?
C3B C2B C1B 121.1(19) . . ?
C2B C3B C4B 122.2(19) . . ?
C2B C3B C6B 115.0(15) . . ?
C4B C3B C6B 116.7(16) . . ?
C3B C4B C5B 109.1(18) . . ?
C4B C5B N1 129.4(17) . . ?
N2 C6B O2B 124.5(13) . . ?
N2 C6B C3B 118.6(12) . . ?
O2B C6B C3B 116.9(14) . . ?
C12 C7 C8 121.0(5) . . ?
C12 C7 N2 118.9(5) . . ?
C8 C7 N2 120.1(5) . . ?
C7 C8 C9 119.8(5) . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 C13 119.8(4) . . ?
C8 C9 C13 120.6(4) . . ?
C11 C10 C9 120.3(4) . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 C14 120.0(4) . . ?
C12 C11 C14 120.4(4) . . ?
C7 C12 C11 119.6(5) . . ?
O4 C13 O3 126.1(4) . . ?
O4 C13 C9 116.6(4) . . ?
O3 C13 C9 117.2(4) . . ?
O6 C14 O5 126.3(4) . . ?
O6 C14 C11 116.5(4) . . ?
O5 C14 C11 117.3(4) . . ?
C6B N2 C6A 91.0(12) . . ?
C6B N2 C7 130.7(8) . . ?
C6A N2 C7 130.7(11) . . ?
C13 O3 Cu1 121.9(3) . 15_445 ?
C13 O4 Cu1 123.0(3) . 6 ?
C14 O5 Cu1 121.8(3) . 14 ?
C14 O6 Cu1 123.1(3) . 5_545 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        89.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.088

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 -0.096 -0.079 -0.001 6812 932 ' '
_database_code_depnum_ccdc_archive 'CCDC 1012810'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_LIFM-10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 Cu N2 O5'
_chemical_formula_weight         347.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'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'
'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'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-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'
'-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'

_cell_length_a                   18.9171(15)
_cell_length_b                   18.9171(15)
_cell_length_c                   37.995(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11775(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3033
_cell_measurement_theta_min      2.9350
_cell_measurement_theta_max      62.9959

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.883
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3150
_exptl_absorpt_coefficient_mu    1.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       \scan
_diffrn_detector_area_resol_mean 16.0855
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9681
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         63.09
_reflns_number_total             4075
_reflns_number_gt                3246
_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)+(0.1497P)²+104.8482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    goem
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4075
_refine_ls_number_parameters     277
_refine_ls_number_restraints     122
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0895
_refine_ls_wR_factor_ref         0.2704
_refine_ls_wR_factor_gt          0.2516
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.004

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 0.52214(5) 0.47797(5) 0.029680(18) 0.0407(4) Uani 1 1 d . . .
N1A N 0.5492(6) 0.4658(7) 0.08477(19) 0.052(5) Uani 0.60 1 d PGU A 1
C1A C 0.6184(5) 0.5335(6) 0.0980(2) 0.067(3) Uani 0.60 1 d PGU A 1
H1AA H 0.6627 0.5665 0.0828 0.080 Uiso 0.60 1 calc PR A 1
C2A C 0.6227(5) 0.5531(5) 0.1335(2) 0.080(4) Uani 0.60 1 d PGU A 1
H2AA H 0.6700 0.5994 0.1426 0.096 Uiso 0.60 1 calc PR A 1
C3A C 0.5578(7) 0.5048(7) 0.15577(18) 0.079(5) Uani 0.60 1 d PGDU A 1
C4A C 0.4887(6) 0.4371(7) 0.1425(2) 0.098(6) Uani 0.60 1 d PGU A 1
H4AA H 0.4443 0.4041 0.1577 0.118 Uiso 0.60 1 calc PR A 1
C5A C 0.4843(5) 0.4175(6) 0.1070(3) 0.083(4) Uani 0.60 1 d PGU A 1
H5AA H 0.4371 0.3712 0.0979 0.100 Uiso 0.60 1 calc PR A 1
C6A C 0.5629(11) 0.5245(9) 0.1960(5) 0.113(5) Uani 0.60 1 d PDU A 1
N1B N 0.5283(15) 0.4490(14) 0.0848(4) 0.040(4) Uani 0.40 1 d PU A 2
C1B C 0.5791(12) 0.5136(11) 0.1072(4) 0.054(4) Uani 0.40 1 d PU A 2
H1BA H 0.6257 0.5598 0.0977 0.065 Uiso 0.40 1 calc PR A 2
C2B C 0.5636(15) 0.5118(13) 0.1420(5) 0.066(4) Uani 0.40 1 d PU A 2
H2BA H 0.5982 0.5564 0.1568 0.079 Uiso 0.40 1 calc PR A 2
C3B C 0.4936(13) 0.4409(11) 0.1562(5) 0.059(3) Uani 0.40 1 d PDU A 2
C4B C 0.4449(10) 0.3737(9) 0.1337(4) 0.050(3) Uani 0.40 1 d PU A 2
H4BA H 0.3995 0.3254 0.1426 0.060 Uiso 0.40 1 calc PR A 2
C5B C 0.4667(11) 0.3811(9) 0.0974(4) 0.045(3) Uani 0.40 1 d PU A 2
H5BA H 0.4363 0.3364 0.0820 0.054 Uiso 0.40 1 calc PR A 2
C6B C 0.4766(10) 0.4345(10) 0.1948(5) 0.073(4) Uani 0.40 1 d PDU A 2
C7 C 0.4817(4) 0.5180(4) 0.24616(17) 0.0564(16) Uani 1 1 d . A .
C8 C 0.5364(4) 0.5907(4) 0.26265(16) 0.0555(16) Uani 1 1 d . . .
H8A H 0.5875 0.6267 0.2520 0.067 Uiso 1 1 calc R . .
C9 C 0.5158(3) 0.6102(4) 0.29477(15) 0.0482(14) Uani 1 1 d . . .
C10 C 0.4437(3) 0.5575(3) 0.31128(14) 0.0433(13) Uani 1 1 d . . .
H10A H 0.4310 0.5709 0.3336 0.052 Uiso 1 1 calc R . .
C11 C 0.3891(4) 0.4840(3) 0.29488(15) 0.0467(13) Uani 1 1 d . . .
C12 C 0.4092(4) 0.4640(4) 0.26246(17) 0.0576(16) Uani 1 1 d . . .
H12A H 0.3730 0.4133 0.2516 0.069 Uiso 1 1 calc R . .
C13 C 0.5711(3) 0.6909(4) 0.31062(14) 0.0454(13) Uani 1 1 d . . .
C14 C 0.3087(4) 0.4296(3) 0.31071(15) 0.0469(14) Uani 1 1 d . . .
N2 N 0.5016(4) 0.4994(4) 0.21235(16) 0.0761(19) Uani 1 1 d D . .
H13A H 0.4589 0.4608 0.2012 0.091 Uiso 1 1 calc R A 1
O2 O 0.6300(2) 0.7424(3) 0.29262(10) 0.0599(12) Uani 1 1 d . . .
O3 O 0.5545(2) 0.7049(3) 0.34161(11) 0.0547(11) Uani 1 1 d . . .
O4 O 0.2588(3) 0.3704(2) 0.29209(11) 0.0611(12) Uani 1 1 d . . .
O5 O 0.2964(2) 0.4468(2) 0.34148(10) 0.0520(10) Uani 1 1 d . . .
O1A O 0.6625(15) 0.5696(12) 0.2125(5) 0.078(6) Uani 0.25 1 d PDU A 1
O1B O 0.4305(14) 0.3313(17) 0.2118(5) 0.089(7) Uani 0.25 1 d PDU A 2
O1C O 0.6286(16) 0.6098(17) 0.2001(6) 0.103(8) Uani 0.25 1 d PU B 3
O1D O 0.397(2) 0.3722(17) 0.2017(7) 0.122(9) Uani 0.25 1 d PU C 4


_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 O3 1.943(4) 8_654 ?
Cu1 O2 1.954(4) 14_455 ?
Cu1 O5 1.967(4) 9_554 ?
Cu1 O4 1.975(4) 15 ?
Cu1 N1B 2.182(16) . ?
Cu1 N1A 2.194(9) . ?
Cu1 Cu1 2.6798(14) 10_665 ?
N1A C1A 1.3900 . ?
N1A C5A 1.3900 . ?
C1A C2A 1.3900 . ?
C1A H1AA 0.9500 . ?
C2A C3A 1.3900 . ?
C2A H2AA 0.9500 . ?
C3A C4A 1.3900 . ?
C3A C6A 1.566(19) . ?
C4A C5A 1.3900 . ?
C4A H4AA 0.9500 . ?
C5A H5AA 0.9500 . ?
C6A N2 1.186(18) . ?
C6A O1A 1.75(3) . ?
N1B C1B 1.40(2) . ?
N1B C5B 1.32(3) . ?
C1B C2B 1.35(3) . ?
C1B H1BA 0.9500 . ?
C2B C3B 1.44(3) . ?
C2B H2BA 0.9500 . ?
C3B C4B 1.42(2) . ?
C3B C6B 1.49(3) . ?
C4B C5B 1.43(2) . ?
C4B H4BA 0.9500 . ?
C5B H5BA 0.9500 . ?
C6B N2 1.264(18) . ?
C6B O1B 1.81(3) . ?
C7 C12 1.380(9) . ?
C7 C8 1.391(9) . ?
C7 N2 1.431(8) . ?
C8 C9 1.386(8) . ?
C8 H8A 0.9500 . ?
C9 C10 1.375(8) . ?
C9 C13 1.479(8) . ?
C10 C11 1.397(8) . ?
C10 H10A 0.9500 . ?
C11 C12 1.396(9) . ?
C11 C14 1.472(8) . ?
C12 H12A 0.9500 . ?
C13 O2 1.254(7) . ?
C13 O3 1.280(7) . ?
C14 O4 1.260(7) . ?
C14 O5 1.266(7) . ?
N2 H13A 0.8800 . ?
O2 Cu1 1.954(4) 15 ?
O3 Cu1 1.943(4) 6_565 ?
O4 Cu1 1.975(4) 14_455 ?
O5 Cu1 1.967(4) 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
O3 Cu1 O2 166.85(17) 8_654 14_455 ?
O3 Cu1 O5 89.39(19) 8_654 9_554 ?
O2 Cu1 O5 89.21(19) 14_455 9_554 ?
O3 Cu1 O4 89.1(2) 8_654 15 ?
O2 Cu1 O4 89.5(2) 14_455 15 ?
O5 Cu1 O4 167.57(17) 9_554 15 ?
O3 Cu1 N1B 108.7(6) 8_654 . ?
O2 Cu1 N1B 84.4(6) 14_455 . ?
O5 Cu1 N1B 100.2(5) 9_554 . ?
O4 Cu1 N1B 91.9(5) 15 . ?
O3 Cu1 N1A 100.7(3) 8_654 . ?
O2 Cu1 N1A 92.2(3) 14_455 . ?
O5 Cu1 N1A 105.8(3) 9_554 . ?
O4 Cu1 N1A 86.6(3) 15 . ?
N1B Cu1 N1A 9.5(7) . . ?
O3 Cu1 Cu1 87.60(12) 8_654 10_665 ?
O2 Cu1 Cu1 79.28(12) 14_455 10_665 ?
O5 Cu1 Cu1 87.76(12) 9_554 10_665 ?
O4 Cu1 Cu1 79.84(12) 15 10_665 ?
N1B Cu1 Cu1 161.8(5) . 10_665 ?
N1A Cu1 Cu1 164.0(3) . 10_665 ?
C1A N1A C5A 120.0 . . ?
C1A N1A Cu1 114.2(5) . . ?
C5A N1A Cu1 118.2(5) . . ?
C2A C1A N1A 120.0 . . ?
C2A C1A H1AA 120.0 . . ?
N1A C1A H1AA 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2AA 120.0 . . ?
C1A C2A H2AA 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A C6A 120.6(9) . . ?
C4A C3A C6A 119.4(9) . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4AA 120.0 . . ?
C5A C4A H4AA 120.0 . . ?
C4A C5A N1A 120.0 . . ?
C4A C5A H5AA 120.0 . . ?
N1A C5A H5AA 120.0 . . ?
N2 C6A C3A 118.9(15) . . ?
N2 C6A O1A 127.5(15) . . ?
C3A C6A O1A 112.8(12) . . ?
C1B N1B C5B 121.0(14) . . ?
C1B N1B Cu1 117.6(15) . . ?
C5B N1B Cu1 117.4(13) . . ?
N1B C1B C2B 121.8(18) . . ?
N1B C1B H1BA 119.1 . . ?
C2B C1B H1BA 119.1 . . ?
C1B C2B C3B 118.5(18) . . ?
C1B C2B H2BA 120.7 . . ?
C3B C2B H2BA 120.7 . . ?
C4B C3B C2B 119.4(17) . . ?
C4B C3B C6B 120.0(15) . . ?
C2B C3B C6B 120.3(16) . . ?
C3B C4B C5B 117.8(15) . . ?
C3B C4B H4BA 121.1 . . ?
C5B C4B H4BA 121.1 . . ?
N1B C5B C4B 121.2(14) . . ?
N1B C5B H5BA 119.4 . . ?
C4B C5B H5BA 119.4 . . ?
N2 C6B C3B 118.7(15) . . ?
N2 C6B O1B 127.0(14) . . ?
C3B C6B O1B 114.0(14) . . ?
C12 C7 C8 120.2(6) . . ?
C12 C7 N2 120.4(6) . . ?
C8 C7 N2 119.4(6) . . ?
C9 C8 C7 119.4(6) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C10 C9 C8 121.2(6) . . ?
C10 C9 C13 119.8(5) . . ?
C8 C9 C13 119.0(5) . . ?
C9 C10 C11 119.4(5) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 C14 119.8(5) . . ?
C10 C11 C14 120.3(5) . . ?
C7 C12 C11 120.0(6) . . ?
C7 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
O2 C13 O3 123.8(5) . . ?
O2 C13 C9 118.4(5) . . ?
O3 C13 C9 117.8(5) . . ?
O4 C14 O5 126.4(6) . . ?
O4 C14 C11 116.4(5) . . ?
O5 C14 C11 117.2(5) . . ?
C6A N2 C6B 85.9(11) . . ?
C6A N2 C7 134.1(10) . . ?
C6B N2 C7 134.2(10) . . ?
C6A N2 H13A 113.0 . . ?
C6B N2 H13A 36.7 . . ?
C7 N2 H13A 112.9 . . ?
C13 O2 Cu1 129.7(4) . 15 ?
C13 O3 Cu1 119.7(4) . 6_565 ?
C14 O4 Cu1 127.5(4) . 14_455 ?
C14 O5 Cu1 118.4(4) . 5 ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        63.09
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.971
_refine_diff_density_min         -1.200
_refine_diff_density_rms         0.108

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 -0.083 -0.067 -0.002 6380 2080 ' '
_database_code_depnum_ccdc_archive 'CCDC 1012811'
