# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s
_database_code_depnum_ccdc_archive 'CCDC 1444337'
_audit_update_record             
;
2015-12-26 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H34 Cu4 N4 O15'
_chemical_formula_weight         1184.97

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c '

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                   7.4800(15)
_cell_length_b                   23.630(5)
_cell_length_c                   12.470(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.05(3)
_cell_angle_gamma                90.00
_cell_volume                     2182.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5011
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1196
_exptl_absorpt_coefficient_mu    2.005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6237
_exptl_absorpt_correction_T_max  0.6898
_exptl_absorpt_process_details   ?

_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  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21262
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4994
_reflns_number_gt                4057
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_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)+(0.1081P)²+21.8368P] 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         4994
_refine_ls_number_parameters     338
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0839
_refine_ls_wR_factor_ref         0.2322
_refine_ls_wR_factor_gt          0.2165
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.075
_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 -0.91183(11) -0.10136(3) -1.13707(6) 0.0255(2) Uani 1 1 d . . .
Cu2 Cu -1.0000 0.0000 -1.0000 0.0213(3) Uani 1 2 d S . .
Cu3 Cu -1.5000 0.0000 -1.0000 0.0183(3) Uani 1 2 d S . .
N1 N -1.0411(8) -0.1694(2) -1.2047(5) 0.0286(12) Uani 1 1 d . . .
N2 N -1.4367(7) -0.4223(2) -1.4299(4) 0.0213(10) Uani 1 1 d . . .
O1 O -1.1812(6) -0.0593(2) -1.1307(4) 0.0292(10) Uani 1 1 d . . .
O2 O -1.4616(6) -0.02559(19) -1.1434(3) 0.0211(9) Uani 1 1 d . . .
O3 O -1.8106(12) -0.0536(7) -1.2916(8) 0.131(6) Uani 1 1 d . . .
O4 O -1.6794(19) -0.1270(6) -1.2287(12) 0.050(5) Uani 0.50(3) 1 d PU . .
O5 O -1.9514(7) -0.0600(2) -1.8882(4) 0.0315(11) Uani 1 1 d . . .
O6 O -1.8905(7) -0.1355(2) -1.9851(4) 0.0295(10) Uani 1 1 d . . .
O7 O -1.7385(7) -0.1078(3) -1.5025(4) 0.0394(13) Uani 1 1 d . . .
O8 O -0.8145(6) -0.03106(18) -1.0753(3) 0.0208(8) Uani 1 1 d . . .
H8A H -0.7048 -0.0378 -1.0256 0.025 Uiso 1 1 calc R . .
H8B H -0.7875 -0.0055 -1.1317 0.025 Uiso 1 1 calc R . .
C1 C -1.3308(8) -0.0471(2) -1.1826(5) 0.0200(11) Uani 1 1 d . . .
C2 C -1.3688(8) -0.0581(3) -1.3030(5) 0.0196(11) Uani 1 1 d . . .
C3 C -1.5386(8) -0.0771(3) -1.3505(5) 0.0234(12) Uani 1 1 d . . .
C4 C -1.5681(9) -0.0873(3) -1.4613(5) 0.0273(14) Uani 1 1 d . . .
C5 C -1.4359(11) -0.0756(4) -1.5248(5) 0.043(2) Uani 1 1 d . . .
H5A H -1.4593 -0.0808 -1.5994 0.052 Uiso 1 1 calc R . .
C6 C -1.2687(11) -0.0563(4) -1.4778(6) 0.044(2) Uani 1 1 d . . .
H6A H -1.1791 -0.0491 -1.5207 0.053 Uiso 1 1 calc R . .
C7 C -1.2346(9) -0.0478(3) -1.3671(6) 0.0322(15) Uani 1 1 d . . .
H7A H -1.1217 -0.0351 -1.3355 0.039 Uiso 1 1 calc R . .
C8 C -1.6814(14) -0.0895(9) -1.2836(8) 0.095(6) Uani 1 1 d . . .
C9 C -1.7487(9) -0.1379(3) -1.6000(5) 0.0309(15) Uani 1 1 d . . .
C10 C -1.8163(9) -0.1108(3) -1.6958(5) 0.0275(13) Uani 1 1 d . . .
H10A H -1.8548 -0.0734 -1.6947 0.033 Uiso 1 1 calc R . .
C11 C -1.8262(9) -0.1398(3) -1.7936(5) 0.0238(12) Uani 1 1 d . . .
C12 C -1.7711(10) -0.1956(3) -1.7939(6) 0.0311(14) Uani 1 1 d . . .
H12A H -1.7761 -0.2151 -1.8591 0.037 Uiso 1 1 calc R . .
C13 C -1.7085(12) -0.2225(3) -1.6975(7) 0.0431(19) Uani 1 1 d . . .
H13A H -1.6746 -0.2604 -1.6980 0.052 Uiso 1 1 calc R . .
C14 C -1.6960(11) -0.1935(4) -1.5999(6) 0.0424(18) Uani 1 1 d . . .
H14A H -1.6523 -0.2116 -1.5352 0.051 Uiso 1 1 calc R . .
C15 C -1.8944(9) -0.1092(3) -1.8979(5) 0.0223(12) Uani 1 1 d . . .
C16 C -1.1153(12) -0.2064(3) -1.1426(6) 0.042(2) Uani 1 1 d . . .
H16A H -1.1065 -0.1996 -1.0686 0.051 Uiso 1 1 calc R . .
C17 C -1.2048(13) -0.2544(4) -1.1850(6) 0.043(2) Uani 1 1 d . . .
H17A H -1.2507 -0.2798 -1.1388 0.052 Uiso 1 1 calc R . .
C18 C -1.2267(9) -0.2651(3) -1.2949(6) 0.0287(14) Uani 1 1 d . . .
C19 C -1.1537(11) -0.2251(3) -1.3591(6) 0.0355(16) Uani 1 1 d . . .
H19A H -1.1659 -0.2298 -1.4338 0.043 Uiso 1 1 calc R . .
C20 C -1.0628(11) -0.1785(3) -1.3107(6) 0.0342(16) Uani 1 1 d . . .
H20A H -1.0150 -0.1523 -1.3546 0.041 Uiso 1 1 calc R . .
C21 C -1.3071(9) -0.3188(3) -1.3408(5) 0.0257(13) Uani 1 1 d . . .
C22 C -1.3952(10) -0.3229(3) -1.4466(6) 0.0293(14) Uani 1 1 d . . .
H22A H -1.4132 -0.2907 -1.4896 0.035 Uiso 1 1 calc R . .
C23 C -1.4553(9) -0.3746(3) -1.4874(5) 0.0269(13) Uani 1 1 d . . .
H23A H -1.5118 -0.3763 -1.5586 0.032 Uiso 1 1 calc R . .
C24 C -1.3592(9) -0.4182(3) -1.3260(5) 0.0265(13) Uani 1 1 d . . .
H24A H -1.3502 -0.4507 -1.2835 0.032 Uiso 1 1 calc R . .
C25 C -1.2928(9) -0.3685(3) -1.2799(5) 0.0272(13) Uani 1 1 d . . .
H25A H -1.2383 -0.3678 -1.2082 0.033 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O8 1.930(4) . ?
Cu1 N1 2.000(6) . ?
Cu1 O6 2.045(5) 1_656 ?
Cu1 O1 2.258(5) . ?
Cu1 O4 2.291(15) 1_655 ?
Cu2 O8 1.927(4) . ?
Cu2 O8 1.927(4) 3_353 ?
Cu2 O5 1.985(5) 3_252 ?
Cu2 O5 1.985(5) 1_656 ?
Cu2 O1 2.417(5) . ?
Cu2 O1 2.417(5) 3_353 ?
Cu3 O2 1.947(4) . ?
Cu3 O2 1.947(4) 3_253 ?
Cu3 N2 2.060(5) 2_252 ?
Cu3 N2 2.060(5) 4_556 ?
N1 C20 1.326(9) . ?
N1 C16 1.339(9) . ?
N2 C23 1.333(8) . ?
N2 C24 1.347(8) . ?
N2 Cu3 2.060(5) 2_242 ?
O1 C1 1.245(7) . ?
O2 C1 1.260(7) . ?
O3 C8 1.28(2) . ?
O4 C8 1.12(2) . ?
O4 Cu1 2.292(15) 1_455 ?
O5 C15 1.252(8) . ?
O5 Cu2 1.985(5) 1_454 ?
O6 C15 1.256(7) . ?
O6 Cu1 2.045(5) 1_454 ?
O7 C4 1.393(8) . ?
O7 C9 1.400(8) . ?
O8 H8A 0.9700 . ?
O8 H8B 0.9700 . ?
C1 C2 1.510(8) . ?
C2 C7 1.389(9) . ?
C2 C3 1.399(8) . ?
C3 C4 1.389(8) . ?
C3 C8 1.475(11) . ?
C4 C5 1.378(10) . ?
C5 C6 1.382(11) . ?
C5 H5A 0.9300 . ?
C6 C7 1.384(10) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C9 C14 1.373(12) . ?
C9 C10 1.387(9) . ?
C10 C11 1.391(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.383(10) . ?
C11 C15 1.512(8) . ?
C12 C13 1.383(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.389(12) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C16 C17 1.384(10) . ?
C16 H16A 0.9300 . ?
C17 C18 1.381(10) . ?
C17 H17A 0.9300 . ?
C18 C19 1.399(10) . ?
C18 C21 1.483(9) . ?
C19 C20 1.389(10) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C22 1.393(9) . ?
C21 C25 1.394(9) . ?
C22 C23 1.373(9) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 C25 1.371(9) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Cu1 N1 173.1(2) . . ?
O8 Cu1 O6 89.68(18) . 1_656 ?
N1 Cu1 O6 92.5(2) . 1_656 ?
O8 Cu1 O1 84.03(18) . . ?
N1 Cu1 O1 89.3(2) . . ?
O6 Cu1 O1 95.5(2) 1_656 . ?
O8 Cu1 O4 99.0(4) . 1_655 ?
N1 Cu1 O4 86.2(4) . 1_655 ?
O6 Cu1 O4 113.0(4) 1_656 1_655 ?
O1 Cu1 O4 151.3(4) . 1_655 ?
O8 Cu2 O8 179.998(1) . 3_353 ?
O8 Cu2 O5 90.18(19) . 3_252 ?
O8 Cu2 O5 89.82(19) 3_353 3_252 ?
O8 Cu2 O5 89.82(19) . 1_656 ?
O8 Cu2 O5 90.18(19) 3_353 1_656 ?
O5 Cu2 O5 179.999(1) 3_252 1_656 ?
O8 Cu2 O1 79.89(17) . . ?
O8 Cu2 O1 100.11(17) 3_353 . ?
O5 Cu2 O1 84.84(19) 3_252 . ?
O5 Cu2 O1 95.16(19) 1_656 . ?
O8 Cu2 O1 100.11(17) . 3_353 ?
O8 Cu2 O1 79.89(17) 3_353 3_353 ?
O5 Cu2 O1 95.2(2) 3_252 3_353 ?
O5 Cu2 O1 84.84(19) 1_656 3_353 ?
O1 Cu2 O1 180.000(1) . 3_353 ?
O2 Cu3 O2 179.998(1) . 3_253 ?
O2 Cu3 N2 86.68(19) . 2_252 ?
O2 Cu3 N2 93.33(19) 3_253 2_252 ?
O2 Cu3 N2 93.33(19) . 4_556 ?
O2 Cu3 N2 86.67(19) 3_253 4_556 ?
N2 Cu3 N2 179.998(1) 2_252 4_556 ?
C20 N1 C16 117.9(6) . . ?
C20 N1 Cu1 122.4(5) . . ?
C16 N1 Cu1 119.7(5) . . ?
C23 N2 C24 117.1(5) . . ?
C23 N2 Cu3 121.7(4) . 2_242 ?
C24 N2 Cu3 120.9(4) . 2_242 ?
C1 O1 Cu1 145.6(4) . . ?
C1 O1 Cu2 126.5(4) . . ?
Cu1 O1 Cu2 81.94(14) . . ?
C1 O2 Cu3 134.7(4) . . ?
C8 O4 Cu1 98.6(11) . 1_455 ?
C15 O5 Cu2 128.9(4) . 1_454 ?
C15 O6 Cu1 126.7(4) . 1_454 ?
C4 O7 C9 115.6(5) . . ?
Cu2 O8 Cu1 105.4(2) . . ?
Cu2 O8 H8A 110.7 . . ?
Cu1 O8 H8A 110.7 . . ?
Cu2 O8 H8B 110.7 . . ?
Cu1 O8 H8B 110.7 . . ?
H8A O8 H8B 108.8 . . ?
O1 C1 O2 125.6(5) . . ?
O1 C1 C2 120.4(5) . . ?
O2 C1 C2 114.0(5) . . ?
C7 C2 C3 119.9(6) . . ?
C7 C2 C1 119.4(6) . . ?
C3 C2 C1 120.6(5) . . ?
C4 C3 C2 119.1(6) . . ?
C4 C3 C8 120.1(6) . . ?
C2 C3 C8 120.7(6) . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 O7 123.4(6) . . ?
C3 C4 O7 115.9(6) . . ?
C4 C5 C6 120.1(6) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C7 120.1(7) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C6 C7 C2 120.1(6) . . ?
C6 C7 H7A 120.0 . . ?
C2 C7 H7A 120.0 . . ?
O4 C8 O3 121.3(12) . . ?
O4 C8 C3 123.8(18) . . ?
O3 C8 C3 115.0(17) . . ?
C14 C9 C10 120.8(7) . . ?
C14 C9 O7 120.3(7) . . ?
C10 C9 O7 118.9(7) . . ?
C9 C10 C11 119.8(7) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
C12 C11 C10 119.5(6) . . ?
C12 C11 C15 121.2(6) . . ?
C10 C11 C15 119.3(6) . . ?
C13 C12 C11 120.1(7) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 120.5(7) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C9 C14 C13 119.2(7) . . ?
C9 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
O5 C15 O6 126.4(6) . . ?
O5 C15 C11 116.0(5) . . ?
O6 C15 C11 117.6(6) . . ?
N1 C16 C17 122.1(7) . . ?
N1 C16 H16A 118.9 . . ?
C17 C16 H16A 118.9 . . ?
C18 C17 C16 120.9(7) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C17 C18 C19 116.2(6) . . ?
C17 C18 C21 121.8(6) . . ?
C19 C18 C21 121.7(6) . . ?
C20 C19 C18 119.6(7) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
N1 C20 C19 123.1(7) . . ?
N1 C20 H20A 118.4 . . ?
C19 C20 H20A 118.4 . . ?
C22 C21 C25 116.6(6) . . ?
C22 C21 C18 122.5(6) . . ?
C25 C21 C18 120.9(6) . . ?
C23 C22 C21 120.0(6) . . ?
C23 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
N2 C23 C22 123.3(6) . . ?
N2 C23 H23A 118.4 . . ?
C22 C23 H23A 118.4 . . ?
N2 C24 C25 123.1(6) . . ?
N2 C24 H24A 118.5 . . ?
C25 C24 H24A 118.5 . . ?
C24 C25 C21 119.9(6) . . ?
C24 C25 H25A 120.0 . . ?
C21 C25 H25A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         4.880
_refine_diff_density_min         -2.582
_refine_diff_density_rms         0.201
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s
_database_code_depnum_ccdc_archive 'CCDC 1444338'
_audit_update_record             
;
2015-12-26 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H34 Cu2 N4 O14'
_chemical_formula_weight         1041.91

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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.8383(6)
_cell_length_b                   9.4782(6)
_cell_length_c                   14.9216(13)
_cell_angle_alpha                91.826(6)
_cell_angle_beta                 95.897(6)
_cell_angle_gamma                103.056(6)
_cell_volume                     1072.46(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4961
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    1.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7681
_exptl_absorpt_correction_T_max  0.8143
_exptl_absorpt_process_details   ?

_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  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6414
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         27.56
_reflns_number_total             4897
_reflns_number_gt                3392
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL

_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)+(0.0452P)²+0.7082P] 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         4897
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_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 0.35551(5) 1.07108(4) 0.08697(4) 0.05377(17) Uani 1 1 d . . .
O1 O 1.1780(3) 1.1936(3) 0.21326(18) 0.0623(7) Uani 1 1 d . . .
O2 O 0.9331(3) 1.2626(2) 0.22499(16) 0.0501(6) Uani 1 1 d . . .
H13A H 0.8788 1.2707 0.2685 0.060 Uiso 1 1 d R . .
O3 O 0.6880(3) 0.9596(3) 0.12496(15) 0.0507(6) Uani 1 1 d . . .
O4 O 0.5342(3) 1.0298(2) 0.22724(15) 0.0422(5) Uani 1 1 d . . .
O7 O 0.5864(3) 0.7489(2) 0.30028(15) 0.0535(6) Uani 1 1 d . . .
O6 O 0.4643(3) 0.8827(2) 0.61538(16) 0.0493(6) Uani 1 1 d . . .
H6A H 0.4573 0.9068 0.6680 0.059 Uiso 1 1 d R . .
O5 O 0.2491(3) 0.6994(3) 0.64452(17) 0.0574(7) Uani 1 1 d . . .
N1 N 0.1781(3) 0.8959(2) 0.08170(18) 0.0349(6) Uani 1 1 d . . .
N2 N 0.4989(3) 1.2605(2) 0.07734(18) 0.0353(6) Uani 1 1 d . . .
C1 C 0.1493(4) 0.8219(3) 0.1559(2) 0.0400(7) Uani 1 1 d . . .
H1A H 0.2231 0.8545 0.2089 0.048 Uiso 1 1 calc R . .
C2 C 0.0150(4) 0.6996(3) 0.1572(2) 0.0356(7) Uani 1 1 d . . .
H2A H -0.0002 0.6514 0.2102 0.043 Uiso 1 1 calc R . .
C3 C -0.0976(3) 0.6487(3) 0.07881(19) 0.0270(6) Uani 1 1 d . . .
C4 C -0.0663(4) 0.7242(3) 0.0022(2) 0.0330(7) Uani 1 1 d . . .
H4A H -0.1369 0.6933 -0.0520 0.040 Uiso 1 1 calc R . .
C5 C 0.0706(4) 0.8460(3) 0.0067(2) 0.0368(7) Uani 1 1 d . . .
H5A H 0.0887 0.8959 -0.0454 0.044 Uiso 1 1 calc R . .
C6 C -0.2421(3) 0.5172(3) 0.07727(19) 0.0267(6) Uani 1 1 d . . .
C7 C -0.3201(4) 0.4748(3) 0.1543(2) 0.0362(7) Uani 1 1 d . . .
H7A H -0.2868 0.5323 0.2076 0.043 Uiso 1 1 calc R . .
C8 C 0.5529(4) 1.3473(3) 0.1516(2) 0.0389(7) Uani 1 1 d . . .
H8A H 0.5025 1.3207 0.2041 0.047 Uiso 1 1 calc R . .
C9 C 0.5677(4) 1.3042(3) 0.0012(2) 0.0361(7) Uani 1 1 d . . .
H9A H 0.5270 1.2476 -0.0521 0.043 Uiso 1 1 calc R . .
C10 C -0.3041(3) 0.4297(3) -0.0008(2) 0.0326(6) Uani 1 1 d . . .
H10A H -0.2589 0.4558 -0.0547 0.039 Uiso 1 1 calc R . .
C21 C 0.9705(4) 1.0444(4) 0.2949(2) 0.0393(7) Uani 1 1 d . . .
C22 C 1.0884(5) 1.0074(5) 0.3604(3) 0.0619(11) Uani 1 1 d . . .
H22A H 1.2033 1.0629 0.3707 0.074 Uiso 1 1 calc R . .
C23 C 1.0365(6) 0.8897(6) 0.4098(3) 0.0773(14) Uani 1 1 d . . .
H23A H 1.1149 0.8678 0.4554 0.093 Uiso 1 1 calc R . .
C24 C 0.8679(6) 0.8029(5) 0.3925(3) 0.0666(11) Uani 1 1 d . . .
H24A H 0.8341 0.7210 0.4250 0.080 Uiso 1 1 calc R . .
C25 C 0.7517(4) 0.8381(4) 0.3275(2) 0.0430(8) Uani 1 1 d . . .
C26 C 0.7983(4) 0.9595(3) 0.27755(19) 0.0327(6) Uani 1 1 d . . .
C27 C 0.4787(4) 0.6896(3) 0.3642(2) 0.0433(8) Uani 1 1 d . . .
C28 C 0.4798(4) 0.7569(3) 0.4469(2) 0.0376(7) Uani 1 1 d . . .
H28A H 0.5581 0.8453 0.4639 0.045 Uiso 1 1 calc R . .
C29 C 0.3626(4) 0.6912(3) 0.5049(2) 0.0366(7) Uani 1 1 d . . .
C30 C 0.2449(5) 0.5610(4) 0.4781(3) 0.0554(10) Uani 1 1 d . . .
H30A H 0.1660 0.5170 0.5170 0.067 Uiso 1 1 calc R . .
C31 C 0.2438(6) 0.4964(4) 0.3946(3) 0.0731(13) Uani 1 1 d . . .
H31 H 0.1638 0.4092 0.3767 0.088 Uiso 1 1 calc R . .
C32 C 0.3612(5) 0.5606(4) 0.3370(3) 0.0613(11) Uani 1 1 d . . .
H32 H 0.3610 0.5171 0.2802 0.074 Uiso 1 1 calc R . .
C33 C 1.0363(4) 1.1720(4) 0.2414(2) 0.0408(8) Uani 1 1 d . . .
C34 C 0.6661(4) 0.9848(3) 0.2032(2) 0.0332(7) Uani 1 1 d . . .
C35 C 0.3552(4) 0.7603(3) 0.5953(2) 0.0397(7) 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 N1 1.904(2) . ?
Cu1 N2 1.909(2) . ?
Cu1 O4 2.489(2) . ?
O1 C33 1.204(3) . ?
O2 C33 1.319(4) . ?
O2 H13A 0.8222 . ?
O3 C34 1.222(3) . ?
O4 C34 1.282(4) . ?
O7 C27 1.388(4) . ?
O7 C25 1.390(4) . ?
O6 C35 1.282(4) . ?
O6 H6A 0.8216 . ?
O5 C35 1.226(4) . ?
N1 C5 1.333(4) . ?
N1 C1 1.341(4) . ?
N2 C8 1.331(4) . ?
N2 C9 1.345(4) . ?
C1 C2 1.381(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.393(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.382(4) . ?
C3 C6 1.481(3) . ?
C4 C5 1.381(4) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.385(4) . ?
C6 C10 1.386(4) . ?
C7 C8 1.378(4) 1_445 ?
C7 H7A 0.9300 . ?
C8 C7 1.378(4) 1_665 ?
C8 H8A 0.9300 . ?
C9 C10 1.376(4) 1_665 ?
C9 H9A 0.9300 . ?
C10 C9 1.376(4) 1_445 ?
C10 H10A 0.9300 . ?
C21 C22 1.383(5) . ?
C21 C26 1.401(4) . ?
C21 C33 1.494(4) . ?
C22 C23 1.365(6) . ?
C22 H22A 0.9300 . ?
C23 C24 1.384(6) . ?
C23 H23A 0.9300 . ?
C24 C25 1.363(5) . ?
C24 H24A 0.9300 . ?
C25 C26 1.391(4) . ?
C26 C34 1.501(4) . ?
C27 C28 1.369(4) . ?
C27 C32 1.375(5) . ?
C28 C29 1.386(4) . ?
C28 H28A 0.9300 . ?
C29 C30 1.384(4) . ?
C29 C35 1.492(5) . ?
C30 C31 1.369(5) . ?
C30 H30A 0.9300 . ?
C31 C32 1.378(5) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N2 168.56(11) . . ?
N1 Cu1 O4 97.77(9) . . ?
N2 Cu1 O4 92.89(9) . . ?
C33 O2 H13A 110.2 . . ?
C34 O4 Cu1 107.20(18) . . ?
C27 O7 C25 120.0(3) . . ?
C35 O6 H6A 108.0 . . ?
C5 N1 C1 117.1(2) . . ?
C5 N1 Cu1 122.2(2) . . ?
C1 N1 Cu1 120.6(2) . . ?
C8 N2 C9 117.5(2) . . ?
C8 N2 Cu1 119.0(2) . . ?
C9 N2 Cu1 122.9(2) . . ?
N1 C1 C2 122.9(3) . . ?
N1 C1 H1A 118.5 . . ?
C2 C1 H1A 118.5 . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 C2 117.2(2) . . ?
C4 C3 C6 121.5(2) . . ?
C2 C3 C6 121.3(3) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
N1 C5 C4 123.6(3) . . ?
N1 C5 H5A 118.2 . . ?
C4 C5 H5A 118.2 . . ?
C7 C6 C10 116.9(2) . . ?
C7 C6 C3 121.4(2) . . ?
C10 C6 C3 121.7(2) . . ?
C8 C7 C6 119.8(3) 1_445 . ?
C8 C7 H7A 120.1 1_445 . ?
C6 C7 H7A 120.1 . . ?
N2 C8 C7 123.1(3) . 1_665 ?
N2 C8 H8A 118.5 . . ?
C7 C8 H8A 118.5 1_665 . ?
N2 C9 C10 122.4(3) . 1_665 ?
N2 C9 H9A 118.8 . . ?
C10 C9 H9A 118.8 1_665 . ?
C9 C10 C6 120.1(3) 1_445 . ?
C9 C10 H10A 119.9 1_445 . ?
C6 C10 H10A 119.9 . . ?
C22 C21 C26 120.2(3) . . ?
C22 C21 C33 117.8(3) . . ?
C26 C21 C33 121.9(3) . . ?
C23 C22 C21 120.2(4) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C22 C23 C24 120.4(4) . . ?
C22 C23 H23A 119.8 . . ?
C24 C23 H23A 119.8 . . ?
C25 C24 C23 119.6(4) . . ?
C25 C24 H24A 120.2 . . ?
C23 C24 H24A 120.2 . . ?
C24 C25 O7 122.8(3) . . ?
C24 C25 C26 121.6(3) . . ?
O7 C25 C26 115.3(3) . . ?
C25 C26 C21 117.9(3) . . ?
C25 C26 C34 118.1(3) . . ?
C21 C26 C34 123.8(3) . . ?
C28 C27 C32 121.4(3) . . ?
C28 C27 O7 123.3(3) . . ?
C32 C27 O7 115.1(3) . . ?
C27 C28 C29 119.0(3) . . ?
C27 C28 H28A 120.5 . . ?
C29 C28 H28A 120.5 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 C35 118.6(3) . . ?
C28 C29 C35 121.5(3) . . ?
C31 C30 C29 120.3(3) . . ?
C31 C30 H30A 119.8 . . ?
C29 C30 H30A 119.8 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 119.3(3) . . ?
C27 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
O1 C33 O2 119.9(3) . . ?
O1 C33 C21 122.4(3) . . ?
O2 C33 C21 117.7(3) . . ?
O3 C34 O4 124.3(3) . . ?
O3 C34 C26 119.0(3) . . ?
O4 C34 C26 116.7(3) . . ?
O5 C35 O6 124.6(3) . . ?
O5 C35 C29 119.7(3) . . ?
O6 C35 C29 115.7(3) . . ?

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
N1 Cu1 O4 C34 100.29(18) . . . . ?
N2 Cu1 O4 C34 -83.88(18) . . . . ?
N2 Cu1 N1 C5 38.3(7) . . . . ?
O4 Cu1 N1 C5 -163.2(2) . . . . ?
N2 Cu1 N1 C1 -137.5(5) . . . . ?
O4 Cu1 N1 C1 21.0(2) . . . . ?
N1 Cu1 N2 C8 116.8(6) . . . . ?
O4 Cu1 N2 C8 -41.9(2) . . . . ?
N1 Cu1 N2 C9 -72.1(6) . . . . ?
O4 Cu1 N2 C9 129.2(2) . . . . ?
C5 N1 C1 C2 -0.3(5) . . . . ?
Cu1 N1 C1 C2 175.7(2) . . . . ?
N1 C1 C2 C3 -0.1(5) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C1 C2 C3 C6 179.5(3) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C6 C3 C4 C5 -179.7(2) . . . . ?
C1 N1 C5 C4 0.1(4) . . . . ?
Cu1 N1 C5 C4 -175.9(2) . . . . ?
C3 C4 C5 N1 0.7(5) . . . . ?
C4 C3 C6 C7 -153.8(3) . . . . ?
C2 C3 C6 C7 27.6(4) . . . . ?
C4 C3 C6 C10 27.0(4) . . . . ?
C2 C3 C6 C10 -151.5(3) . . . . ?
C10 C6 C7 C8 2.9(4) . . . 1_445 ?
C3 C6 C7 C8 -176.2(3) . . . 1_445 ?
C9 N2 C8 C7 -3.0(4) . . . 1_665 ?
Cu1 N2 C8 C7 168.6(2) . . . 1_665 ?
C8 N2 C9 C10 3.4(4) . . . 1_665 ?
Cu1 N2 C9 C10 -167.8(2) . . . 1_665 ?
C7 C6 C10 C9 -2.5(4) . . . 1_445 ?
C3 C6 C10 C9 176.7(3) . . . 1_445 ?
C26 C21 C22 C23 -1.4(6) . . . . ?
C33 C21 C22 C23 -178.4(4) . . . . ?
C21 C22 C23 C24 2.6(7) . . . . ?
C22 C23 C24 C25 -2.0(7) . . . . ?
C23 C24 C25 O7 173.5(4) . . . . ?
C23 C24 C25 C26 0.2(6) . . . . ?
C27 O7 C25 C24 47.5(5) . . . . ?
C27 O7 C25 C26 -138.8(3) . . . . ?
C24 C25 C26 C21 1.0(5) . . . . ?
O7 C25 C26 C21 -172.8(3) . . . . ?
C24 C25 C26 C34 176.1(3) . . . . ?
O7 C25 C26 C34 2.3(4) . . . . ?
C22 C21 C26 C25 -0.4(5) . . . . ?
C33 C21 C26 C25 176.5(3) . . . . ?
C22 C21 C26 C34 -175.1(3) . . . . ?
C33 C21 C26 C34 1.7(5) . . . . ?
C25 O7 C27 C28 30.9(5) . . . . ?
C25 O7 C27 C32 -152.8(3) . . . . ?
C32 C27 C28 C29 1.6(5) . . . . ?
O7 C27 C28 C29 177.7(3) . . . . ?
C27 C28 C29 C30 -1.1(5) . . . . ?
C27 C28 C29 C35 -178.9(3) . . . . ?
C28 C29 C30 C31 0.1(6) . . . . ?
C35 C29 C30 C31 178.0(4) . . . . ?
C29 C30 C31 C32 0.5(7) . . . . ?
C28 C27 C32 C31 -1.0(6) . . . . ?
O7 C27 C32 C31 -177.4(4) . . . . ?
C30 C31 C32 C27 -0.1(7) . . . . ?
C22 C21 C33 O1 42.1(5) . . . . ?
C26 C21 C33 O1 -134.8(3) . . . . ?
C22 C21 C33 O2 -137.9(3) . . . . ?
C26 C21 C33 O2 45.1(4) . . . . ?
Cu1 O4 C34 O3 -4.2(3) . . . . ?
Cu1 O4 C34 C26 177.05(18) . . . . ?
C25 C26 C34 O3 -105.0(3) . . . . ?
C21 C26 C34 O3 69.8(4) . . . . ?
C25 C26 C34 O4 73.8(3) . . . . ?
C21 C26 C34 O4 -111.5(3) . . . . ?
C30 C29 C35 O5 1.8(5) . . . . ?
C28 C29 C35 O5 179.6(3) . . . . ?
C30 C29 C35 O6 -178.2(3) . . . . ?
C28 C29 C35 O6 -0.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.061
