# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_sm079

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H29 Cu1.50 N16 O3'
_chemical_formula_weight         648.91

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/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0662(3)
_cell_length_b                   14.7659(3)
_cell_length_c                   15.3925(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.296(2)
_cell_angle_gamma                90.00
_cell_volume                     2969.70(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13306
_cell_measurement_theta_min      2.9787
_cell_measurement_theta_max      30.4403

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1338
_exptl_absorpt_coefficient_mu    1.137
_exptl_absorpt_correction_T_min  0.7565
_exptl_absorpt_correction_T_max  0.8302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25450
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5226
_reflns_number_gt                4777
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0525P)²+2.5493P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5226
_refine_ls_number_parameters     476
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.097
_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 0.5000 0.5000 0.0000 0.01568(12) Uani 1 2 d S . .
Cu2 Cu 0.51254(2) 0.286005(19) -0.091235(18) 0.01861(11) Uani 1 1 d . . .
O1 O 0.45664(16) 0.16434(13) -0.00190(12) 0.0315(4) Uani 1 1 d . . .
N1 N 0.59455(16) 0.40318(13) 0.04754(12) 0.0188(4) Uani 1 1 d . . .
N2 N 0.60208(16) 0.32237(13) 0.01059(13) 0.0197(4) Uani 1 1 d . . .
N3 N 0.66541(16) 0.27022(14) 0.05652(13) 0.0226(5) Uani 1 1 d . . .
N4 N 0.65291(17) 0.40671(14) 0.11814(13) 0.0222(5) Uani 1 1 d . . .
N5 N 0.40878(15) 0.37453(13) -0.04880(13) 0.0190(4) Uani 1 1 d . . .
N6 N 0.32414(17) 0.34856(15) -0.03405(15) 0.0272(5) Uani 1 1 d . . .
N7 N 0.2424(2) 0.3246(2) -0.0176(2) 0.0527(8) Uani 1 1 d . . .
N8 N 0.42511(16) 0.50225(13) 0.11446(13) 0.0191(4) Uani 1 1 d . . .
N9 N 0.37029(16) 0.43172(14) 0.14163(13) 0.0216(4) Uani 1 1 d . . .
N10 N 0.41436(17) 0.57196(14) 0.16779(13) 0.0231(5) Uani 1 1 d . . .
N11 N 0.35149(18) 0.54832(15) 0.23214(14) 0.0267(5) Uani 1 1 d . . .
N12 N 0.12080(16) 0.29261(14) 0.35366(13) 0.0220(5) Uani 1 1 d . . .
N13 N 0.91230(16) 0.24892(14) 0.31484(13) 0.0217(4) Uani 1 1 d . . .
N14 N 0.4604(2) 0.13556(18) 0.14202(15) 0.0390(6) Uani 1 1 d . . .
C1 C 0.69525(19) 0.32403(17) 0.12214(16) 0.0213(5) Uani 1 1 d . . .
C2 C 0.7682(2) 0.29687(17) 0.18970(16) 0.0226(5) Uani 1 1 d . . .
C3 C 0.8066(2) 0.20906(18) 0.19366(18) 0.0286(6) Uani 1 1 d . . .
H3 H 0.7846 0.1645 0.1532 0.034 Uiso 1 1 calc R . .
C4 C 0.8027(2) 0.35921(18) 0.25060(17) 0.0297(6) Uani 1 1 d . . .
H4 H 0.7770 0.4194 0.2504 0.036 Uiso 1 1 calc R . .
C5 C 0.3263(2) 0.46180(17) 0.21377(16) 0.0215(5) Uani 1 1 d . . .
C6 C 0.2557(2) 0.40510(17) 0.26371(16) 0.0233(5) Uani 1 1 d . . .
C7 C 0.2101(2) 0.33007(18) 0.22387(17) 0.0263(6) Uani 1 1 d . . .
H7 H 0.2247 0.3162 0.1650 0.032 Uiso 1 1 calc R . .
C8 C 0.1444(2) 0.27678(17) 0.27014(17) 0.0250(6) Uani 1 1 d . . .
H8 H 0.1141 0.2262 0.2419 0.030 Uiso 1 1 calc R . .
C9 C 0.1648(2) 0.36415(18) 0.39237(17) 0.0271(6) Uani 1 1 d . . .
H9 H 0.1493 0.3760 0.4515 0.033 Uiso 1 1 calc R . .
C10 C 0.2318(2) 0.42147(18) 0.35000(17) 0.0294(6) Uani 1 1 d . . .
H10 H 0.2612 0.4716 0.3797 0.035 Uiso 1 1 calc R . .
C11 C 0.8745(2) 0.33295(18) 0.31124(18) 0.0297(6) Uani 1 1 d . . .
H11 H 0.8981 0.3763 0.3523 0.036 Uiso 1 1 calc R . .
C12 C 0.8772(2) 0.18788(19) 0.25742(18) 0.0293(6) Uani 1 1 d . . .
H12 H 0.9021 0.1275 0.2608 0.035 Uiso 1 1 calc R . .
C13 C 0.5204(4) 0.0538(2) 0.1329(2) 0.0606(11) Uani 1 1 d . . .
H13A H 0.4983 0.0211 0.0806 0.091 Uiso 1 1 calc R . .
H13B H 0.5106 0.0153 0.1840 0.091 Uiso 1 1 calc R . .
H13C H 0.5930 0.0697 0.1278 0.091 Uiso 1 1 calc R . .
C14 C 0.4313(5) 0.1624(4) 0.2293(3) 0.098(2) Uani 1 1 d . . .
H14A H 0.3878 0.2164 0.2264 0.147 Uiso 1 1 calc R . .
H14B H 0.4929 0.1758 0.2635 0.147 Uiso 1 1 calc R . .
H14C H 0.3935 0.1129 0.2569 0.147 Uiso 1 1 calc R . .
C15 C 0.4364(3) 0.1847(2) 0.0734(2) 0.0393(7) Uani 1 1 d . . .
H15 H 0.4008 0.2399 0.0829 0.047 Uiso 1 1 calc R . .
C111 C 0.8478(14) 0.4103(17) 0.9609(13) 0.101(7) Uani 0.67(3) 1 d P A 1
H11A H 0.8875 0.4242 0.9087 0.151 Uiso 0.67(3) 1 calc PR A 1
H11B H 0.7889 0.4512 0.9643 0.151 Uiso 0.67(3) 1 calc PR A 1
H11C H 0.8237 0.3475 0.9580 0.151 Uiso 0.67(3) 1 calc PR A 1
C222 C 0.9847(17) 0.3541(13) 1.0469(16) 0.152(10) Uani 0.67(3) 1 d P A 1
H22A H 1.0142 0.3652 1.1046 0.228 Uiso 0.67(3) 1 calc PR A 1
H22B H 1.0383 0.3592 1.0029 0.228 Uiso 0.67(3) 1 calc PR A 1
H22C H 0.9550 0.2932 1.0450 0.228 Uiso 0.67(3) 1 calc PR A 1
N111 N 0.9052(17) 0.4207(12) 1.0294(11) 0.038(3) Uani 0.67(3) 1 d PU A 1
C333 C 0.8975(10) 0.4904(6) 1.0890(9) 0.039(3) Uani 0.67(3) 1 d PU A 1
H333 H 0.8478 0.5363 1.0788 0.047 Uiso 0.67(3) 1 calc PR A 1
O111 O 0.9544(9) 0.4966(7) 1.1579(4) 0.092(4) Uani 0.67(3) 1 d PU A 1
C011 C 0.8385(14) 0.4386(16) 0.957(2) 0.038(4) Uani 0.33(3) 1 d P A 2
H01A H 0.7967 0.4936 0.9603 0.057 Uiso 0.33(3) 1 calc PR A 2
H01B H 0.7938 0.3858 0.9497 0.057 Uiso 0.33(3) 1 calc PR A 2
H01C H 0.8847 0.4429 0.9072 0.057 Uiso 0.33(3) 1 calc PR A 2
C022 C 0.971(2) 0.345(2) 1.0468(16) 0.069(7) Uani 0.33(3) 1 d PDU A 2
H02A H 0.9907 0.3254 1.1056 0.103 Uiso 0.33(3) 1 calc PR A 2
H02B H 1.0330 0.3566 1.0129 0.103 Uiso 0.33(3) 1 calc PR A 2
H02C H 0.9312 0.2967 1.0187 0.103 Uiso 0.33(3) 1 calc PR A 2
N011 N 0.910(4) 0.427(3) 1.052(2) 0.044(6) Uani 0.33(3) 1 d PDU A 2
C033 C 0.923(3) 0.493(2) 1.117(2) 0.10(2) Uani 0.33(3) 1 d PD A 2
H033 H 0.8766 0.5423 1.1169 0.124 Uiso 0.33(3) 1 calc PR A 2
O011 O 0.967(5) 0.493(5) 1.156(5) 0.39(5) Uani 0.33(3) 1 d P A 2
C444 C 0.4602(9) 0.5176(8) 0.6328(10) 0.135(6) Uani 0.587(10) 1 d PD B 1
H44A H 0.4358 0.5047 0.6916 0.203 Uiso 0.587(10) 1 calc PR B 1
H44B H 0.5323 0.5359 0.6354 0.203 Uiso 0.587(10) 1 calc PR B 1
H44C H 0.4535 0.4631 0.5969 0.203 Uiso 0.587(10) 1 calc PR B 1
C555 C 0.4382(11) 0.6715(10) 0.6291(8) 0.109(4) Uani 0.587(10) 1 d PD B 1
H55A H 0.3936 0.7209 0.6095 0.164 Uiso 0.587(10) 1 calc PR B 1
H55B H 0.5079 0.6819 0.6080 0.164 Uiso 0.587(10) 1 calc PR B 1
H55C H 0.4389 0.6694 0.6927 0.164 Uiso 0.587(10) 1 calc PR B 1
N222 N 0.4012(11) 0.5884(8) 0.5961(8) 0.069(3) Uani 0.587(10) 1 d PD B 1
C666 C 0.3095(6) 0.5654(6) 0.5580(5) 0.065(2) Uani 0.587(10) 1 d PD B 1
H666 H 0.2692 0.6132 0.5347 0.078 Uiso 0.587(10) 1 calc PR B 1
O222 O 0.2768(7) 0.4918(8) 0.5518(7) 0.091(3) Uani 0.587(10) 1 d P B 1
C044 C 0.3846(19) 0.6245(9) 0.4839(10) 0.134(8) Uani 0.413(10) 1 d P B 2
H04A H 0.3331 0.5874 0.4541 0.201 Uiso 0.413(10) 1 calc PR B 2
H04B H 0.4461 0.6288 0.4480 0.201 Uiso 0.413(10) 1 calc PR B 2
H04C H 0.3569 0.6854 0.4938 0.201 Uiso 0.413(10) 1 calc PR B 2
C055 C 0.475(3) 0.651(3) 0.576(3) 0.27(3) Uani 0.413(10) 1 d P B 2
H05A H 0.4784 0.6907 0.5250 0.407 Uiso 0.413(10) 1 calc PR B 2
H05B H 0.5422 0.6239 0.5867 0.407 Uiso 0.413(10) 1 calc PR B 2
H05C H 0.4532 0.6854 0.6265 0.407 Uiso 0.413(10) 1 calc PR B 2
N022 N 0.409(2) 0.5865(19) 0.5604(11) 0.084(6) Uani 0.413(10) 1 d P B 2
C066 C 0.3662(18) 0.5130(13) 0.5956(11) 0.111(6) Uani 0.413(10) 1 d P B 2
H066 H 0.3810 0.5002 0.6548 0.133 Uiso 0.413(10) 1 calc PR B 2
O022 O 0.314(3) 0.4650(15) 0.5597(17) 0.26(2) Uani 0.413(10) 1 d P B 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 N8 2.020(2) 3_665 ?
Cu1 N8 2.020(2) . ?
Cu1 N1 2.024(2) . ?
Cu1 N1 2.024(2) 3_665 ?
Cu1 N5 2.325(2) . ?
Cu1 N5 2.325(2) 3_665 ?
Cu2 N5 1.996(2) . ?
Cu2 N13 2.013(2) 4_565 ?
Cu2 N12 2.020(2) 4_665 ?
Cu2 N2 2.024(2) . ?
Cu2 O1 2.3795(19) . ?
O1 C15 1.228(4) . ?
N1 N4 1.325(3) . ?
N1 N2 1.326(3) . ?
N2 N3 1.331(3) . ?
N3 C1 1.341(3) . ?
N4 C1 1.342(3) . ?
N5 N6 1.193(3) . ?
N6 N7 1.155(3) . ?
N8 N10 1.324(3) . ?
N8 N9 1.333(3) . ?
N9 C5 1.329(3) . ?
N10 N11 1.337(3) . ?
N11 C5 1.349(3) . ?
N12 C9 1.341(3) . ?
N12 C8 1.344(3) . ?
N12 Cu2 2.020(2) 4_566 ?
N13 C11 1.337(3) . ?
N13 C12 1.341(3) . ?
N13 Cu2 2.013(2) 4_666 ?
N14 C15 1.318(4) . ?
N14 C13 1.447(4) . ?
N14 C14 1.453(5) . ?
C1 C2 1.463(3) . ?
C2 C4 1.387(4) . ?
C2 C3 1.391(4) . ?
C3 C12 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C11 1.375(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.466(4) . ?
C6 C10 1.387(4) . ?
C6 C7 1.398(4) . ?
C7 C8 1.367(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C111 N111 1.30(3) . ?
C111 H11A 0.9800 . ?
C111 H11B 0.9800 . ?
C111 H11C 0.9800 . ?
C222 N111 1.455(16) . ?
C222 H22A 0.9800 . ?
C222 H22B 0.9800 . ?
C222 H22C 0.9800 . ?
N111 C333 1.383(16) . ?
C333 O111 1.296(15) . ?
C333 H333 0.9500 . ?
C011 N011 1.74(5) . ?
C011 H01A 0.9800 . ?
C011 H01B 0.9800 . ?
C011 H01C 0.9800 . ?
C022 N011 1.46(2) . ?
C022 H02A 0.9800 . ?
C022 H02B 0.9800 . ?
C022 H02C 0.9800 . ?
N011 C033 1.41(2) . ?
C033 O011 0.83(7) . ?
C033 H033 0.9500 . ?
C444 N222 1.416(13) . ?
C444 H44A 0.9800 . ?
C444 H44B 0.9800 . ?
C444 H44C 0.9800 . ?
C555 N222 1.413(14) . ?
C555 H55A 0.9800 . ?
C555 H55B 0.9800 . ?
C555 H55C 0.9800 . ?
N222 C666 1.373(14) . ?
C666 O222 1.172(12) . ?
C666 H666 0.9500 . ?
C044 N022 1.34(2) . ?
C044 H04A 0.9800 . ?
C044 H04B 0.9800 . ?
C044 H04C 0.9800 . ?
C055 N022 1.30(4) . ?
C055 H05A 0.9800 . ?
C055 H05B 0.9800 . ?
C055 H05C 0.9800 . ?
N022 C066 1.33(3) . ?
C066 O022 1.13(3) . ?
C066 H066 0.9500 . ?

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
N8 Cu1 N8 180.00(11) 3_665 . ?
N8 Cu1 N1 90.36(8) 3_665 . ?
N8 Cu1 N1 89.64(8) . . ?
N8 Cu1 N1 89.64(8) 3_665 3_665 ?
N8 Cu1 N1 90.36(8) . 3_665 ?
N1 Cu1 N1 180.00(10) . 3_665 ?
N8 Cu1 N5 87.41(7) 3_665 . ?
N8 Cu1 N5 92.59(7) . . ?
N1 Cu1 N5 82.24(7) . . ?
N1 Cu1 N5 97.76(7) 3_665 . ?
N8 Cu1 N5 92.59(7) 3_665 3_665 ?
N8 Cu1 N5 87.41(7) . 3_665 ?
N1 Cu1 N5 97.76(7) . 3_665 ?
N1 Cu1 N5 82.24(7) 3_665 3_665 ?
N5 Cu1 N5 180.00(11) . 3_665 ?
N5 Cu2 N13 87.84(8) . 4_565 ?
N5 Cu2 N12 172.86(8) . 4_665 ?
N13 Cu2 N12 90.32(8) 4_565 4_665 ?
N5 Cu2 N2 87.92(8) . . ?
N13 Cu2 N2 174.70(9) 4_565 . ?
N12 Cu2 N2 94.27(8) 4_665 . ?
N5 Cu2 O1 95.41(8) . . ?
N13 Cu2 O1 91.21(8) 4_565 . ?
N12 Cu2 O1 91.52(8) 4_665 . ?
N2 Cu2 O1 86.02(7) . . ?
C15 O1 Cu2 115.40(19) . . ?
N4 N1 N2 110.09(19) . . ?
N4 N1 Cu1 128.04(16) . . ?
N2 N1 Cu1 121.82(15) . . ?
N1 N2 N3 109.89(18) . . ?
N1 N2 Cu2 121.82(15) . . ?
N3 N2 Cu2 127.83(16) . . ?
N2 N3 C1 103.58(19) . . ?
N1 N4 C1 103.73(19) . . ?
N6 N5 Cu2 118.92(17) . . ?
N6 N5 Cu1 131.95(17) . . ?
Cu2 N5 Cu1 106.24(9) . . ?
N7 N6 N5 178.1(3) . . ?
N10 N8 N9 110.73(19) . . ?
N10 N8 Cu1 127.35(16) . . ?
N9 N8 Cu1 121.63(15) . . ?
C5 N9 N8 103.67(19) . . ?
N8 N10 N11 108.90(19) . . ?
N10 N11 C5 104.0(2) . . ?
C9 N12 C8 117.5(2) . . ?
C9 N12 Cu2 124.45(18) . 4_566 ?
C8 N12 Cu2 117.81(17) . 4_566 ?
C11 N13 C12 118.1(2) . . ?
C11 N13 Cu2 120.44(17) . 4_666 ?
C12 N13 Cu2 121.31(17) . 4_666 ?
C15 N14 C13 120.5(3) . . ?
C15 N14 C14 121.9(3) . . ?
C13 N14 C14 117.5(3) . . ?
N3 C1 N4 112.7(2) . . ?
N3 C1 C2 124.0(2) . . ?
N4 C1 C2 123.3(2) . . ?
C4 C2 C3 118.2(2) . . ?
C4 C2 C1 120.4(2) . . ?
C3 C2 C1 121.3(2) . . ?
C12 C3 C2 118.8(2) . . ?
C12 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C11 C4 C2 119.3(2) . . ?
C11 C4 H4 120.3 . . ?
C2 C4 H4 120.3 . . ?
N9 C5 N11 112.7(2) . . ?
N9 C5 C6 121.5(2) . . ?
N11 C5 C6 125.7(2) . . ?
C10 C6 C7 117.4(2) . . ?
C10 C6 C5 123.2(2) . . ?
C7 C6 C5 119.4(2) . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
N12 C8 C7 123.1(2) . . ?
N12 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
N12 C9 C10 122.9(2) . . ?
N12 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
C9 C10 C6 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C6 C10 H10 120.3 . . ?
N13 C11 C4 122.7(2) . . ?
N13 C11 H11 118.6 . . ?
C4 C11 H11 118.6 . . ?
N13 C12 C3 122.8(2) . . ?
N13 C12 H12 118.6 . . ?
C3 C12 H12 118.6 . . ?
N14 C13 H13A 109.5 . . ?
N14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N14 C14 H14A 109.5 . . ?
N14 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N14 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 N14 124.7(3) . . ?
O1 C15 H15 117.6 . . ?
N14 C15 H15 117.6 . . ?
C111 N111 C333 125.7(15) . . ?
C111 N111 C222 118.6(16) . . ?
C333 N111 C222 115.7(16) . . ?
O111 C333 N111 123.5(12) . . ?
O111 C333 H333 118.2 . . ?
N111 C333 H333 118.2 . . ?
N011 C011 H01A 109.5 . . ?
N011 C011 H01B 109.5 . . ?
H01A C011 H01B 109.5 . . ?
N011 C011 H01C 109.5 . . ?
H01A C011 H01C 109.5 . . ?
H01B C011 H01C 109.5 . . ?
N011 C022 H02A 109.5 . . ?
N011 C022 H02B 109.5 . . ?
H02A C022 H02B 109.5 . . ?
N011 C022 H02C 109.5 . . ?
H02A C022 H02C 109.5 . . ?
H02B C022 H02C 109.5 . . ?
C033 N011 C022 123(3) . . ?
C033 N011 C011 127(2) . . ?
C022 N011 C011 109(3) . . ?
O011 C033 N011 126(7) . . ?
O011 C033 H033 116.8 . . ?
N011 C033 H033 116.8 . . ?
C666 N222 C555 131.7(12) . . ?
C666 N222 C444 117.4(10) . . ?
C555 N222 C444 108.2(12) . . ?
O222 C666 N222 125.5(9) . . ?
O222 C666 H666 117.2 . . ?
N222 C666 H666 117.2 . . ?
N022 C044 H04A 109.5 . . ?
N022 C044 H04B 109.5 . . ?
H04A C044 H04B 109.5 . . ?
N022 C044 H04C 109.5 . . ?
H04A C044 H04C 109.5 . . ?
H04B C044 H04C 109.5 . . ?
N022 C055 H05A 109.5 . . ?
N022 C055 H05B 109.5 . . ?
H05A C055 H05B 109.5 . . ?
N022 C055 H05C 109.5 . . ?
H05A C055 H05C 109.5 . . ?
H05B C055 H05C 109.5 . . ?
C055 N022 C066 143(3) . . ?
C055 N022 C044 90(3) . . ?
C066 N022 C044 127(2) . . ?
O022 C066 N022 124(2) . . ?
O022 C066 H066 117.8 . . ?
N022 C066 H066 117.8 . . ?

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
N5 Cu2 O1 C15 -42.8(2) . . . . ?
N13 Cu2 O1 C15 -130.7(2) 4_565 . . . ?
N12 Cu2 O1 C15 138.9(2) 4_665 . . . ?
N2 Cu2 O1 C15 44.8(2) . . . . ?
N8 Cu1 N1 N4 123.3(2) 3_665 . . . ?
N8 Cu1 N1 N4 -56.7(2) . . . . ?
N1 Cu1 N1 N4 -14(59) 3_665 . . . ?
N5 Cu1 N1 N4 -149.3(2) . . . . ?
N5 Cu1 N1 N4 30.7(2) 3_665 . . . ?
N8 Cu1 N1 N2 -59.63(19) 3_665 . . . ?
N8 Cu1 N1 N2 120.37(19) . . . . ?
N1 Cu1 N1 N2 163(59) 3_665 . . . ?
N5 Cu1 N1 N2 27.71(18) . . . . ?
N5 Cu1 N1 N2 -152.29(18) 3_665 . . . ?
N4 N1 N2 N3 0.4(3) . . . . ?
Cu1 N1 N2 N3 -177.11(15) . . . . ?
N4 N1 N2 Cu2 173.15(16) . . . . ?
Cu1 N1 N2 Cu2 -4.4(3) . . . . ?
N5 Cu2 N2 N1 -26.05(19) . . . . ?
N13 Cu2 N2 N1 -63.0(9) 4_565 . . . ?
N12 Cu2 N2 N1 147.15(19) 4_665 . . . ?
O1 Cu2 N2 N1 -121.63(19) . . . . ?
N5 Cu2 N2 N3 145.3(2) . . . . ?
N13 Cu2 N2 N3 108.4(9) 4_565 . . . ?
N12 Cu2 N2 N3 -41.5(2) 4_665 . . . ?
O1 Cu2 N2 N3 49.7(2) . . . . ?
N1 N2 N3 C1 -0.2(3) . . . . ?
Cu2 N2 N3 C1 -172.40(17) . . . . ?
N2 N1 N4 C1 -0.4(3) . . . . ?
Cu1 N1 N4 C1 176.92(17) . . . . ?
N13 Cu2 N5 N6 52.9(2) 4_565 . . . ?
N12 Cu2 N5 N6 128.1(6) 4_665 . . . ?
N2 Cu2 N5 N6 -123.9(2) . . . . ?
O1 Cu2 N5 N6 -38.10(19) . . . . ?
N13 Cu2 N5 Cu1 -144.10(9) 4_565 . . . ?
N12 Cu2 N5 Cu1 -68.9(7) 4_665 . . . ?
N2 Cu2 N5 Cu1 39.09(9) . . . . ?
O1 Cu2 N5 Cu1 124.89(8) . . . . ?
N8 Cu1 N5 N6 -150.1(2) 3_665 . . . ?
N8 Cu1 N5 N6 29.9(2) . . . . ?
N1 Cu1 N5 N6 119.2(2) . . . . ?
N1 Cu1 N5 N6 -60.8(2) 3_665 . . . ?
N5 Cu1 N5 N6 55(100) 3_665 . . . ?
N8 Cu1 N5 Cu2 49.99(9) 3_665 . . . ?
N8 Cu1 N5 Cu2 -130.01(9) . . . . ?
N1 Cu1 N5 Cu2 -40.72(9) . . . . ?
N1 Cu1 N5 Cu2 139.28(9) 3_665 . . . ?
N5 Cu1 N5 Cu2 -105(100) 3_665 . . . ?
Cu2 N5 N6 N7 131(10) . . . . ?
Cu1 N5 N6 N7 -27(10) . . . . ?
N8 Cu1 N8 N10 76.54(17) 3_665 . . . ?
N1 Cu1 N8 N10 119.8(2) . . . . ?
N1 Cu1 N8 N10 -60.2(2) 3_665 . . . ?
N5 Cu1 N8 N10 -158.0(2) . . . . ?
N5 Cu1 N8 N10 22.0(2) 3_665 . . . ?
N8 Cu1 N8 N9 -110.2(2) 3_665 . . . ?
N1 Cu1 N8 N9 -66.89(18) . . . . ?
N1 Cu1 N8 N9 113.11(18) 3_665 . . . ?
N5 Cu1 N8 N9 15.32(18) . . . . ?
N5 Cu1 N8 N9 -164.68(18) 3_665 . . . ?
N10 N8 N9 C5 -0.2(3) . . . . ?
Cu1 N8 N9 C5 -174.52(16) . . . . ?
N9 N8 N10 N11 0.1(3) . . . . ?
Cu1 N8 N10 N11 174.01(16) . . . . ?
N8 N10 N11 C5 0.0(3) . . . . ?
N2 N3 C1 N4 0.0(3) . . . . ?
N2 N3 C1 C2 -178.5(2) . . . . ?
N1 N4 C1 N3 0.3(3) . . . . ?
N1 N4 C1 C2 178.7(2) . . . . ?
N3 C1 C2 C4 173.8(3) . . . . ?
N4 C1 C2 C4 -4.5(4) . . . . ?
N3 C1 C2 C3 -4.8(4) . . . . ?
N4 C1 C2 C3 177.0(3) . . . . ?
C4 C2 C3 C12 -0.2(4) . . . . ?
C1 C2 C3 C12 178.3(3) . . . . ?
C3 C2 C4 C11 1.3(4) . . . . ?
C1 C2 C4 C11 -177.3(3) . . . . ?
N8 N9 C5 N11 0.2(3) . . . . ?
N8 N9 C5 C6 178.2(2) . . . . ?
N10 N11 C5 N9 -0.2(3) . . . . ?
N10 N11 C5 C6 -178.0(2) . . . . ?
N9 C5 C6 C10 160.5(3) . . . . ?
N11 C5 C6 C10 -21.9(4) . . . . ?
N9 C5 C6 C7 -19.0(4) . . . . ?
N11 C5 C6 C7 158.7(3) . . . . ?
C10 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C7 C8 179.8(2) . . . . ?
C9 N12 C8 C7 -0.3(4) . . . . ?
Cu2 N12 C8 C7 174.5(2) 4_566 . . . ?
C6 C7 C8 N12 -0.1(4) . . . . ?
C8 N12 C9 C10 0.4(4) . . . . ?
Cu2 N12 C9 C10 -173.9(2) 4_566 . . . ?
N12 C9 C10 C6 -0.2(4) . . . . ?
C7 C6 C10 C9 -0.2(4) . . . . ?
C5 C6 C10 C9 -179.6(3) . . . . ?
C12 N13 C11 C4 -1.0(4) . . . . ?
Cu2 N13 C11 C4 -177.3(2) 4_666 . . . ?
C2 C4 C11 N13 -0.7(5) . . . . ?
C11 N13 C12 C3 2.1(4) . . . . ?
Cu2 N13 C12 C3 178.3(2) 4_666 . . . ?
C2 C3 C12 N13 -1.5(5) . . . . ?
Cu2 O1 C15 N14 -139.2(3) . . . . ?
C13 N14 C15 O1 4.2(6) . . . . ?
C14 N14 C15 O1 -178.1(4) . . . . ?
C111 N111 C333 O111 178(2) . . . . ?
C222 N111 C333 O111 -2(3) . . . . ?
C022 N011 C033 O011 4(9) . . . . ?
C011 N011 C033 O011 -164(6) . . . . ?
C555 N222 C666 O222 -160.5(13) . . . . ?
C444 N222 C666 O222 -1.5(19) . . . . ?
C055 N022 C066 O022 -173(5) . . . . ?
C044 N022 C066 O022 12(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 940211'
#######################################################################
#
#                 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_sm053

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 Cu N10 O2'
_chemical_formula_weight         387.82

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   'P b c n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   11.9883(7)
_cell_length_b                   16.0417(6)
_cell_length_c                   13.0715(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2513.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4200
_cell_measurement_theta_min      2.9737
_cell_measurement_theta_max      32.5216

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.025
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_min  0.7890
_exptl_absorpt_correction_T_max  0.8493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19402
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2218
_reflns_number_gt                1709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0923P)²+2.7945P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2218
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1858
_refine_ls_wR_factor_gt          0.1743
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 0.0000 0.0000 0.5000 0.0273(3) Uani 1 2 d S . .
N1 N 0.0955(3) -0.1035(2) 0.4697(3) 0.0346(8) Uani 1 1 d . . .
N2 N 0.1074(3) 0.0764(2) 0.4280(2) 0.0352(8) Uani 1 1 d . . .
N3 N 0.1311(4) 0.0805(3) 0.3300(3) 0.0618(13) Uani 1 1 d . . .
N4 N 0.1993(5) 0.1449(3) 0.3155(3) 0.0749(17) Uani 1 1 d . . .
N5 N 0.1562(3) 0.1376(2) 0.4786(3) 0.0400(9) Uani 1 1 d . . .
C1 C 0.1445(5) -0.1479(3) 0.5441(3) 0.0497(13) Uani 1 1 d . . .
H1 H 0.1351 -0.1298 0.6127 0.060 Uiso 1 1 calc R . .
C2 C 0.2067(5) -0.2174(3) 0.5270(4) 0.0538(14) Uani 1 1 d . . .
H2 H 0.2406 -0.2458 0.5827 0.065 Uiso 1 1 calc R . .
C3 C 0.2206(4) -0.2466(3) 0.4276(3) 0.0422(11) Uani 1 1 d . . .
C4 C 0.1690(5) -0.2017(3) 0.3511(4) 0.0649(17) Uani 1 1 d . . .
H4 H 0.1754 -0.2192 0.2819 0.078 Uiso 1 1 calc R . .
C5 C 0.1084(5) -0.1319(3) 0.3749(3) 0.0567(15) Uani 1 1 d . . .
H5 H 0.0738 -0.1021 0.3206 0.068 Uiso 1 1 calc R . .
C6 C 0.2134(4) 0.1786(3) 0.4069(3) 0.0427(11) Uani 1 1 d . . .
O1 O 0.1036(3) 0.0248(2) 0.6534(2) 0.0453(8) 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 N2 2.011(3) . ?
Cu1 N2 2.011(3) 5_556 ?
Cu1 N1 2.056(3) 5_556 ?
Cu1 N1 2.056(3) . ?
Cu1 O1 2.391(3) 5_556 ?
Cu1 O1 2.391(3) . ?
N1 C5 1.329(5) . ?
N1 C1 1.340(6) . ?
N2 N3 1.314(5) . ?
N2 N5 1.320(5) . ?
N3 N4 1.331(6) . ?
N4 C6 1.323(6) . ?
N5 C6 1.335(6) . ?
C1 C2 1.359(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(6) . ?
C3 C6 1.463(6) 7_655 ?
C4 C5 1.370(7) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C3 1.463(6) 7_665 ?

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
N2 Cu1 N2 180.00(14) . 5_556 ?
N2 Cu1 N1 87.38(14) . 5_556 ?
N2 Cu1 N1 92.62(14) 5_556 5_556 ?
N2 Cu1 N1 92.62(14) . . ?
N2 Cu1 N1 87.38(14) 5_556 . ?
N1 Cu1 N1 180.0 5_556 . ?
N2 Cu1 O1 92.38(12) . 5_556 ?
N2 Cu1 O1 87.62(12) 5_556 5_556 ?
N1 Cu1 O1 90.39(13) 5_556 5_556 ?
N1 Cu1 O1 89.61(13) . 5_556 ?
N2 Cu1 O1 87.62(12) . . ?
N2 Cu1 O1 92.38(12) 5_556 . ?
N1 Cu1 O1 89.61(13) 5_556 . ?
N1 Cu1 O1 90.39(13) . . ?
O1 Cu1 O1 180.0 5_556 . ?
C5 N1 C1 116.3(4) . . ?
C5 N1 Cu1 121.4(3) . . ?
C1 N1 Cu1 122.2(3) . . ?
N3 N2 N5 110.8(3) . . ?
N3 N2 Cu1 128.7(3) . . ?
N5 N2 Cu1 120.2(3) . . ?
N2 N3 N4 108.1(3) . . ?
C6 N4 N3 105.5(4) . . ?
N2 N5 C6 104.1(3) . . ?
N1 C1 C2 123.9(4) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 116.6(4) . . ?
C4 C3 C6 122.5(4) . 7_655 ?
C2 C3 C6 120.9(4) . 7_655 ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 123.5(4) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N4 C6 N5 111.5(4) . . ?
N4 C6 C3 124.9(4) . 7_665 ?
N5 C6 C3 123.5(4) . 7_665 ?

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
N2 Cu1 N1 C5 -67.5(4) . . . . ?
N2 Cu1 N1 C5 112.5(4) 5_556 . . . ?
N1 Cu1 N1 C5 -178(84) 5_556 . . . ?
O1 Cu1 N1 C5 24.9(4) 5_556 . . . ?
O1 Cu1 N1 C5 -155.1(4) . . . . ?
N2 Cu1 N1 C1 115.1(4) . . . . ?
N2 Cu1 N1 C1 -64.9(4) 5_556 . . . ?
N1 Cu1 N1 C1 4(83) 5_556 . . . ?
O1 Cu1 N1 C1 -152.5(4) 5_556 . . . ?
O1 Cu1 N1 C1 27.5(4) . . . . ?
N2 Cu1 N2 N3 151(100) 5_556 . . . ?
N1 Cu1 N2 N3 -112.4(4) 5_556 . . . ?
N1 Cu1 N2 N3 67.6(4) . . . . ?
O1 Cu1 N2 N3 -22.1(4) 5_556 . . . ?
O1 Cu1 N2 N3 157.9(4) . . . . ?
N2 Cu1 N2 N5 -36(100) 5_556 . . . ?
N1 Cu1 N2 N5 60.3(3) 5_556 . . . ?
N1 Cu1 N2 N5 -119.7(3) . . . . ?
O1 Cu1 N2 N5 150.6(3) 5_556 . . . ?
O1 Cu1 N2 N5 -29.4(3) . . . . ?
N5 N2 N3 N4 1.3(6) . . . . ?
Cu1 N2 N3 N4 174.6(4) . . . . ?
N2 N3 N4 C6 -0.7(7) . . . . ?
N3 N2 N5 C6 -1.4(5) . . . . ?
Cu1 N2 N5 C6 -175.3(3) . . . . ?
C5 N1 C1 C2 1.4(8) . . . . ?
Cu1 N1 C1 C2 179.0(4) . . . . ?
N1 C1 C2 C3 -1.1(9) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
C1 C2 C3 C6 -179.6(5) . . . 7_655 ?
C2 C3 C4 C5 0.4(9) . . . . ?
C6 C3 C4 C5 -179.8(5) 7_655 . . . ?
C1 N1 C5 C4 -0.8(8) . . . . ?
Cu1 N1 C5 C4 -178.4(5) . . . . ?
C3 C4 C5 N1 -0.1(10) . . . . ?
N3 N4 C6 N5 -0.1(7) . . . . ?
N3 N4 C6 C3 -177.7(5) . . . 7_665 ?
N2 N5 C6 N4 0.9(6) . . . . ?
N2 N5 C6 C3 178.5(4) . . . 7_665 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.099

# 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 0.000 0.500 -0.007 582 82 ' '
2 0.500 0.000 -0.011 582 82 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 940212'
