# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Leroy Cronin'
_publ_contact_author_email       LEE@CHEM.GLA.AC.UK

_publ_section_title              
;
Supramolecular self-assembly and anion-dependence of
copper(II) complexes with cationic Dihydro-Imidazo Phenanthridinium
(DIP)- containing ligands
;
loop_
_publ_author_name
'Leroy Cronin'
'Phil. J. Kitson'
'De-Liang Long.'
'Alexis D C Parenty'
;
Yu-Fei Song
;
'Robert J Thatcher'

# Attachment 'compound1.cif'

data_ys026013
_database_code_depnum_ccdc_archive 'CCDC 678279'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C84 H71 B4 Br3 Cu F16 N12'
_chemical_formula_weight         1899.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   28.553(2)
_cell_length_b                   8.2201(6)
_cell_length_c                   16.7163(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.746(3)
_cell_angle_gamma                90.00
_cell_volume                     3854.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3386
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      21.4

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1914
_exptl_absorpt_coefficient_mu    1.934
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7735
_exptl_absorpt_correction_T_max  0.8606
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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 Apex CCD'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            23213
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         22.18
_reflns_number_total             4747
_reflns_number_gt                3725
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex
_computing_cell_refinement       Apex
_computing_data_reduction        Apex
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Wingx

_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)+(0.0000P)²+15.2444P] 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     SHELXL
_refine_ls_extinction_coef       0.00048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4747
_refine_ls_number_parameters     562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_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 0.0000 0.5000 0.5000 0.0256(3) Uani 1 2 d S . .
Br1 Br 0.05000(7) 0.67926(17) 0.59797(8) 0.0298(4) Uani 0.592(2) 1 d P A 1
Br1' Br 0.02164(10) 0.7034(2) 0.59975(11) 0.0246(5) Uani 0.408(2) 1 d P A 2
Br2 Br 0.13929(5) 0.72364(19) 0.65342(9) 0.0305(6) Uani 0.408(2) 1 d P A 2
Br3 Br 0.3626(5) -0.0255(18) 0.4423(8) 0.044(4) Uiso 0.05 1 d P B 2
B1 B 0.4130(3) 0.1882(9) 0.2465(4) 0.0273(18) Uani 1 1 d . . .
B2 B 0.1381(3) 0.4249(10) 0.3803(5) 0.035(2) Uani 1 1 d . . .
F1 F 0.39630(12) 0.2515(5) 0.16880(19) 0.0444(10) Uani 1 1 d . . .
F2 F 0.45841(12) 0.1266(5) 0.2512(2) 0.0472(11) Uani 1 1 d . . .
F3 F 0.38234(13) 0.0644(4) 0.2610(2) 0.0466(10) Uani 1 1 d . . .
F4 F 0.41371(14) 0.3105(5) 0.3032(2) 0.0508(11) Uani 1 1 d . . .
F5 F 0.17351(16) 0.3121(6) 0.3885(3) 0.0795(15) Uani 1 1 d . . .
F6 F 0.09461(15) 0.3451(6) 0.3630(2) 0.0678(13) Uani 1 1 d . . .
F7 F 0.14067(14) 0.5058(5) 0.4534(2) 0.0609(12) Uani 1 1 d . . .
F8 F 0.1406(2) 0.5311(6) 0.3205(3) 0.1029(19) Uani 1 1 d . . .
N1 N 0.17408(18) 0.0223(6) 0.5004(3) 0.0272(13) Uani 1 1 d . . .
N2 N 0.11272(18) 0.1342(6) 0.5422(3) 0.0289(13) Uani 1 1 d . . .
N3 N 0.00612(18) 0.3308(6) 0.5838(3) 0.0229(12) Uani 1 1 d . A .
N4 N 0.34739(18) 0.7631(6) 0.6734(3) 0.0256(12) Uani 1 1 d . . .
N5 N 0.41783(18) 0.7075(6) 0.6463(3) 0.0279(13) Uani 1 1 d . . .
N6 N 0.43452(18) 0.8152(6) 0.4973(3) 0.0333(13) Uani 1 1 d . . .
C7 C 0.2434(2) 0.1842(7) 0.6105(3) 0.0232(15) Uani 1 1 d . C .
C11 C 0.1823(2) 0.2695(7) 0.6863(3) 0.0268(15) Uani 1 1 d . . .
H11 H 0.1499 0.2717 0.6924 0.032 Uiso 1 1 calc R . .
C23 C 0.2774(2) 0.8404(7) 0.7269(3) 0.0278(16) Uani 1 1 d . . .
H23 H 0.2965 0.9036 0.7681 0.033 Uiso 1 1 calc R . .
C22 C 0.2985(2) 0.7550(7) 0.6699(3) 0.0246(15) Uani 1 1 d . . .
C12 C 0.1944(2) 0.1967(7) 0.6174(3) 0.0245(15) Uani 1 1 d . . .
C5 C 0.3041(2) 0.0684(7) 0.5348(4) 0.0278(16) Uani 1 1 d . C 1
H5 H 0.3289 0.1231 0.5705 0.033 Uiso 1 1 calc R C 1
C34 C 0.3712(2) 0.6824(7) 0.6234(3) 0.0232(15) Uani 1 1 d . . .
C38 C 0.4695(2) 0.7258(7) 0.5413(3) 0.0257(15) Uani 1 1 d . . .
C3 C 0.2794(3) -0.1116(8) 0.4223(4) 0.0345(17) Uani 1 1 d . C 1
H3 H 0.2874 -0.1779 0.3803 0.041 Uiso 1 1 calc R C 1
C29 C 0.2686(2) 0.4901(7) 0.4846(3) 0.0302(16) Uani 1 1 d . . .
H29 H 0.2350 0.4825 0.4793 0.036 Uiso 1 1 calc R . .
C16 C 0.0855(2) 0.2775(7) 0.5581(4) 0.0329(16) Uani 1 1 d . A .
H16A H 0.0715 0.3292 0.5055 0.039 Uiso 1 1 calc R . .
H16B H 0.1075 0.3570 0.5900 0.039 Uiso 1 1 calc R . .
C24 C 0.2287(2) 0.8321(7) 0.7228(4) 0.0316(17) Uani 1 1 d . A .
H24 H 0.2143 0.8879 0.7617 0.038 Uiso 1 1 calc R . .
C1 C 0.2214(2) 0.0023(7) 0.4923(3) 0.0263(15) Uani 1 1 d . C .
C42 C 0.4451(3) 0.8879(8) 0.4301(4) 0.0360(18) Uani 1 1 d . . .
H42 H 0.4213 0.9533 0.3980 0.043 Uiso 1 1 calc R . .
C6 C 0.2568(2) 0.0884(7) 0.5452(3) 0.0240(15) Uani 1 1 d . . .
C36 C 0.4271(2) 0.8336(8) 0.7096(4) 0.0332(17) Uani 1 1 d . . .
H36A H 0.4357 0.9382 0.6868 0.040 Uiso 1 1 calc R . .
H36B H 0.4531 0.8004 0.7544 0.040 Uiso 1 1 calc R . .
C27 C 0.2709(2) 0.6621(7) 0.6086(3) 0.0237(15) Uani 1 1 d . . .
C13 C 0.1604(2) 0.1223(7) 0.5546(4) 0.0277(16) Uani 1 1 d . . .
C9 C 0.2641(2) 0.3366(7) 0.7359(4) 0.0315(17) Uani 1 1 d . C .
H9 H 0.2874 0.3902 0.7749 0.038 Uiso 1 1 calc R . .
C39 C 0.5144(2) 0.7088(8) 0.5227(4) 0.0350(17) Uani 1 1 d . . .
H39 H 0.5385 0.6470 0.5563 0.042 Uiso 1 1 calc R . .
C40 C 0.5230(3) 0.7861(8) 0.4524(4) 0.045(2) Uani 1 1 d . . .
H40 H 0.5533 0.7784 0.4372 0.053 Uiso 1 1 calc R . .
C31 C 0.3395(3) 0.4256(7) 0.4346(4) 0.0347(17) Uani 1 1 d . . .
H31 H 0.3546 0.3733 0.3955 0.042 Uiso 1 1 calc R . .
C37 C 0.4578(2) 0.6403(8) 0.6152(3) 0.0313(16) Uani 1 1 d . . .
H37A H 0.4510 0.5247 0.6012 0.038 Uiso 1 1 calc R . .
H37B H 0.4863 0.6437 0.6591 0.038 Uiso 1 1 calc R . .
C18 C 0.0499(2) 0.1220(8) 0.6638(4) 0.0336(17) Uani 1 1 d . A .
H18 H 0.0777 0.0565 0.6765 0.040 Uiso 1 1 calc R . .
C10 C 0.2165(2) 0.3376(7) 0.7451(4) 0.0313(16) Uani 1 1 d . . .
H10 H 0.2078 0.3854 0.7920 0.038 Uiso 1 1 calc R . .
C19 C 0.0128(3) 0.1017(8) 0.7048(4) 0.0339(17) Uani 1 1 d . . .
H19 H 0.0150 0.0226 0.7467 0.041 Uiso 1 1 calc R . .
C8 C 0.2776(2) 0.2583(7) 0.6704(3) 0.0262(15) Uani 1 1 d . . .
H8 H 0.3103 0.2549 0.6661 0.031 Uiso 1 1 calc R C .
C2 C 0.2329(2) -0.0987(7) 0.4312(4) 0.0333(17) Uani 1 1 d . . .
H2 H 0.2086 -0.1575 0.3963 0.040 Uiso 1 1 calc R C 1
C21 C -0.0292(2) 0.3075(7) 0.6243(3) 0.0281(16) Uani 1 1 d . . .
H21 H -0.0571 0.3719 0.6103 0.034 Uiso 1 1 calc R A .
C33 C 0.3443(2) 0.5870(7) 0.5569(3) 0.0229(15) Uani 1 1 d . . .
C4 C 0.3150(2) -0.0283(8) 0.4744(4) 0.0339(17) Uani 1 1 d . C 1
H4 H 0.3473 -0.0387 0.4680 0.041 Uiso 1 1 calc R C 1
C20 C -0.0270(2) 0.1952(8) 0.6853(3) 0.0300(16) Uani 1 1 d . A .
H20 H -0.0528 0.1827 0.7134 0.036 Uiso 1 1 calc R . .
C32 C 0.3661(2) 0.5114(7) 0.4974(3) 0.0307(16) Uani 1 1 d . . .
H32 H 0.3996 0.5201 0.5010 0.037 Uiso 1 1 calc R . .
C26 C 0.2213(2) 0.6588(8) 0.6055(4) 0.0319(17) Uani 1 1 d . A .
H26 H 0.2017 0.5981 0.5639 0.038 Uiso 1 1 calc R . .
C28 C 0.2948(2) 0.5778(7) 0.5500(3) 0.0272(16) Uani 1 1 d . . .
C25 C 0.2007(2) 0.7410(7) 0.6611(4) 0.0314(16) Uani 1 1 d . . .
C30 C 0.2903(3) 0.4154(7) 0.4285(4) 0.0372(18) Uani 1 1 d . . .
H30 H 0.2717 0.3561 0.3851 0.045 Uiso 1 1 calc R . .
C17 C 0.0461(2) 0.2393(7) 0.6037(3) 0.0239(15) Uani 1 1 d . . .
C14 C 0.1329(2) -0.0471(8) 0.4441(4) 0.0372(18) Uani 1 1 d . . .
H14A H 0.1329 -0.1674 0.4470 0.045 Uiso 1 1 calc R . .
H14B H 0.1328 -0.0132 0.3873 0.045 Uiso 1 1 calc R . .
C35 C 0.3802(2) 0.8469(8) 0.7388(4) 0.0304(16) Uani 1 1 d . . .
H35A H 0.3816 0.7917 0.7918 0.036 Uiso 1 1 calc R . .
H35B H 0.3709 0.9619 0.7437 0.036 Uiso 1 1 calc R . .
C15 C 0.0906(2) 0.0249(8) 0.4758(4) 0.0342(17) Uani 1 1 d . . .
H15A H 0.0694 0.0862 0.4325 0.041 Uiso 1 1 calc R . .
H15B H 0.0718 -0.0615 0.4966 0.041 Uiso 1 1 calc R . .
C41 C 0.4871(3) 0.8729(8) 0.4061(4) 0.0383(18) Uani 1 1 d . . .
H41 H 0.4919 0.9225 0.3569 0.046 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 N3 1.959(4) 3_566 ?
Cu1 N3 1.959(4) . ?
Cu1 Br1' 2.3605(18) 3_566 ?
Cu1 Br1' 2.3605(18) . ?
Cu1 Br1 2.4534(14) 3_566 ?
Cu1 Br1 2.4534(14) . ?
Br2 C25 1.739(7) . ?
B1 F2 1.379(8) . ?
B1 F4 1.380(8) . ?
B1 F3 1.393(8) . ?
B1 F1 1.398(7) . ?
B2 F8 1.339(8) . ?
B2 F5 1.360(9) . ?
B2 F7 1.382(8) . ?
B2 F6 1.387(9) . ?
N1 C13 1.335(7) . ?
N1 C1 1.391(7) . ?
N1 C14 1.476(7) . ?
N2 C13 1.342(7) . ?
N2 C16 1.463(7) . ?
N2 C15 1.475(7) . ?
N3 C21 1.328(7) . ?
N3 C17 1.356(7) . ?
N4 C34 1.346(7) . ?
N4 C22 1.388(7) . ?
N4 C35 1.471(7) . ?
N5 C34 1.332(7) . ?
N5 C37 1.449(7) . ?
N5 C36 1.469(7) . ?
N6 C38 1.343(7) . ?
N6 C42 1.356(8) . ?
C7 C8 1.401(8) . ?
C7 C12 1.428(8) . ?
C7 C6 1.453(8) . ?
C11 C10 1.369(8) . ?
C11 C12 1.398(8) . ?
C23 C24 1.379(8) . ?
C23 C22 1.407(8) . ?
C22 C27 1.397(8) . ?
C12 C13 1.427(8) . ?
C5 C4 1.367(8) . ?
C5 C6 1.403(8) . ?
C34 C33 1.456(8) . ?
C38 C39 1.382(8) . ?
C38 C37 1.512(8) . ?
C3 C2 1.367(8) . ?
C3 C4 1.391(9) . ?
C29 C30 1.361(8) . ?
C29 C28 1.404(8) . ?
C16 C17 1.505(8) . ?
C24 C25 1.400(8) . ?
C1 C2 1.403(8) . ?
C1 C6 1.404(8) . ?
C42 C41 1.341(9) . ?
C36 C35 1.512(8) . ?
C27 C26 1.409(8) . ?
C27 C28 1.466(8) . ?
C9 C8 1.386(8) . ?
C9 C10 1.395(8) . ?
C39 C40 1.396(9) . ?
C40 C41 1.365(9) . ?
C31 C32 1.370(8) . ?
C31 C30 1.394(9) . ?
C18 C19 1.376(8) . ?
C18 C17 1.382(8) . ?
C19 C20 1.361(8) . ?
C21 C20 1.369(8) . ?
C33 C28 1.399(8) . ?
C33 C32 1.413(8) . ?
C26 C25 1.366(8) . ?
C14 C15 1.528(8) . ?

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
N3 Cu1 N3 180.000(1) 3_566 . ?
N3 Cu1 Br1' 91.21(14) 3_566 3_566 ?
N3 Cu1 Br1' 88.79(14) . 3_566 ?
N3 Cu1 Br1' 88.79(14) 3_566 . ?
N3 Cu1 Br1' 91.21(14) . . ?
Br1' Cu1 Br1' 180.0 3_566 . ?
N3 Cu1 Br1 89.20(14) 3_566 3_566 ?
N3 Cu1 Br1 90.80(14) . 3_566 ?
Br1' Cu1 Br1 19.97(4) 3_566 3_566 ?
Br1' Cu1 Br1 160.03(4) . 3_566 ?
N3 Cu1 Br1 90.80(14) 3_566 . ?
N3 Cu1 Br1 89.20(14) . . ?
Br1' Cu1 Br1 160.03(4) 3_566 . ?
Br1' Cu1 Br1 19.97(4) . . ?
Br1 Cu1 Br1 180.0 3_566 . ?
F2 B1 F4 109.6(6) . . ?
F2 B1 F3 109.7(5) . . ?
F4 B1 F3 109.9(5) . . ?
F2 B1 F1 110.1(5) . . ?
F4 B1 F1 109.0(5) . . ?
F3 B1 F1 108.5(5) . . ?
F8 B2 F5 112.2(7) . . ?
F8 B2 F7 110.2(7) . . ?
F5 B2 F7 108.9(6) . . ?
F8 B2 F6 108.9(6) . . ?
F5 B2 F6 108.6(6) . . ?
F7 B2 F6 108.0(6) . . ?
C13 N1 C1 123.4(5) . . ?
C13 N1 C14 111.8(5) . . ?
C1 N1 C14 124.3(5) . . ?
C13 N2 C16 126.1(5) . . ?
C13 N2 C15 110.6(5) . . ?
C16 N2 C15 117.3(5) . . ?
C21 N3 C17 118.6(5) . . ?
C21 N3 Cu1 119.4(4) . . ?
C17 N3 Cu1 121.9(4) . . ?
C34 N4 C22 124.7(5) . . ?
C34 N4 C35 111.5(5) . . ?
C22 N4 C35 123.4(5) . . ?
C34 N5 C37 130.6(5) . . ?
C34 N5 C36 110.6(5) . . ?
C37 N5 C36 118.6(5) . . ?
C38 N6 C42 115.9(6) . . ?
C8 C7 C12 118.3(5) . . ?
C8 C7 C6 121.8(6) . . ?
C12 C7 C6 119.9(5) . . ?
C10 C11 C12 120.9(6) . . ?
C24 C23 C22 119.7(6) . . ?
N4 C22 C27 118.8(5) . . ?
N4 C22 C23 120.1(5) . . ?
C27 C22 C23 121.1(6) . . ?
C11 C12 C13 123.3(6) . . ?
C11 C12 C7 119.6(5) . . ?
C13 C12 C7 116.9(5) . . ?
C4 C5 C6 121.2(6) . . ?
N5 C34 N4 109.8(5) . . ?
N5 C34 C33 131.3(6) . . ?
N4 C34 C33 119.0(6) . . ?
N6 C38 C39 124.0(6) . . ?
N6 C38 C37 116.5(6) . . ?
C39 C38 C37 119.5(6) . . ?
C2 C3 C4 120.4(6) . . ?
C30 C29 C28 121.6(6) . . ?
N2 C16 C17 113.4(5) . . ?
C23 C24 C25 119.7(6) . . ?
N1 C1 C2 120.3(6) . . ?
N1 C1 C6 118.5(5) . . ?
C2 C1 C6 121.2(6) . . ?
C41 C42 N6 123.9(6) . . ?
C5 C6 C1 117.4(6) . . ?
C5 C6 C7 123.4(6) . . ?
C1 C6 C7 119.1(6) . . ?
N5 C36 C35 103.4(5) . . ?
C22 C27 C26 117.5(5) . . ?
C22 C27 C28 118.7(6) . . ?
C26 C27 C28 123.8(5) . . ?
N1 C13 N2 110.9(5) . . ?
N1 C13 C12 121.2(6) . . ?
N2 C13 C12 127.9(6) . . ?
C8 C9 C10 120.7(6) . . ?
C38 C39 C40 117.3(6) . . ?
C41 C40 C39 119.0(7) . . ?
C32 C31 C30 119.5(6) . . ?
N5 C37 C38 115.2(5) . . ?
C19 C18 C17 118.9(6) . . ?
C11 C10 C9 119.8(6) . . ?
C20 C19 C18 120.0(6) . . ?
C9 C8 C7 120.5(6) . . ?
C3 C2 C1 119.3(6) . . ?
N3 C21 C20 123.0(6) . . ?
C28 C33 C32 119.3(5) . . ?
C28 C33 C34 118.2(5) . . ?
C32 C33 C34 122.4(6) . . ?
C5 C4 C3 120.5(6) . . ?
C19 C20 C21 118.6(6) . . ?
C31 C32 C33 120.9(6) . . ?
C25 C26 C27 121.6(6) . . ?
C33 C28 C29 118.3(6) . . ?
C33 C28 C27 120.5(5) . . ?
C29 C28 C27 121.1(6) . . ?
C26 C25 C24 120.4(6) . . ?
C26 C25 Br2 117.7(5) . . ?
C24 C25 Br2 121.9(5) . . ?
C29 C30 C31 120.3(6) . . ?
N3 C17 C18 120.9(6) . . ?
N3 C17 C16 115.8(5) . . ?
C18 C17 C16 123.3(6) . . ?
N1 C14 C15 102.5(5) . . ?
N4 C35 C36 101.9(5) . . ?
N2 C15 C14 103.9(5) . . ?
C42 C41 C40 119.8(7) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        22.18
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.42
_refine_diff_density_rms         0.07

# Attachment 'compound2.cif'

data_ys02701
_database_code_depnum_ccdc_archive 'CCDC 678280'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 Br2 Cu N4 O3'
_chemical_formula_weight         597.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   8.8546(5)
_cell_length_b                   11.6779(7)
_cell_length_c                   12.0660(7)
_cell_angle_alpha                63.335(3)
_cell_angle_beta                 76.612(3)
_cell_angle_gamma                78.007(3)
_cell_volume                     1076.90(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6539
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      25.6

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             590
_exptl_absorpt_coefficient_mu    4.756
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2521
_exptl_absorpt_correction_T_max  0.7634
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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 Apex CCD'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            16793
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3787
_reflns_number_gt                3088
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex
_computing_cell_refinement       Apex
_computing_data_reduction        Apex
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Wingx

_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)+(0.0408P)²+5.6902P] 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     SHELXL
_refine_ls_extinction_coef       none
_refine_ls_extinction_expression none
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.98344(7) 0.65678(7) 0.57695(6) 0.0256(2) Uani 1 1 d . . .
Br1 Br 1.11065(6) 0.65127(6) 0.37964(5) 0.02684(19) Uani 1 1 d . . .
Br2 Br 0.86189(6) 0.57038(7) 0.79329(5) 0.0275(3) Uani 0.946(3) 1 d P . .
Br2' Br 0.8639(15) 0.6699(16) 0.7522(13) 0.045(5) Uiso 0.054(3) 1 d P . .
O1 O 0.6783(5) 0.9178(4) 0.4017(5) 0.0536(13) Uani 1 1 d . . .
O2 O 0.7818(4) 0.7253(4) 0.5109(4) 0.0325(10) Uani 1 1 d . . .
O3 O 0.8850(5) 0.8910(4) 0.4837(5) 0.0456(12) Uani 1 1 d . . .
N1 N 1.4433(5) 0.1017(5) 0.8065(4) 0.0232(10) Uani 1 1 d . . .
N2 N 1.3569(5) 0.3100(4) 0.7194(4) 0.0243(10) Uani 1 1 d . . .
N3 N 1.1845(5) 0.6503(4) 0.6271(4) 0.0223(10) Uani 1 1 d . . .
N4 N 0.7795(5) 0.8498(4) 0.4661(5) 0.0300(11) Uani 1 1 d . . .
C1 C 1.4351(6) -0.0295(5) 0.8834(5) 0.0237(12) Uani 1 1 d . . .
C2 C 1.5492(6) -0.1246(6) 0.8621(5) 0.0293(13) Uani 1 1 d . . .
H2 H 1.6387 -0.1004 0.7996 0.035 Uiso 1 1 calc R . .
C3 C 1.5299(7) -0.2522(6) 0.9325(5) 0.0303(13) Uani 1 1 d . . .
H3 H 1.6072 -0.3163 0.9188 0.036 Uiso 1 1 calc R . .
C4 C 1.3990(7) -0.2895(6) 1.0236(6) 0.0316(13) Uani 1 1 d . . .
H4 H 1.3843 -0.3781 1.0686 0.038 Uiso 1 1 calc R . .
C5 C 1.2901(6) -0.1966(6) 1.0484(5) 0.0280(13) Uani 1 1 d . . .
H5 H 1.2025 -0.2228 1.1125 0.034 Uiso 1 1 calc R . .
C6 C 1.3061(6) -0.0639(5) 0.9807(5) 0.0226(12) Uani 1 1 d . . .
C7 C 1.2002(6) 0.0376(5) 1.0080(5) 0.0226(12) Uani 1 1 d . . .
C8 C 1.0865(6) 0.0074(6) 1.1170(5) 0.0260(12) Uani 1 1 d . . .
H8 H 1.0725 -0.0802 1.1706 0.031 Uiso 1 1 calc R . .
C9 C 0.9958(6) 0.1040(6) 1.1461(5) 0.0301(14) Uani 1 1 d . . .
H9 H 0.9188 0.0824 1.2195 0.036 Uiso 1 1 calc R . .
C10 C 1.0152(6) 0.2334(6) 1.0695(5) 0.0304(13) Uani 1 1 d . . .
H10 H 0.9532 0.2989 1.0919 0.036 Uiso 1 1 calc R . .
C11 C 1.1234(6) 0.2663(6) 0.9618(5) 0.0253(12) Uani 1 1 d . . .
H11 H 1.1371 0.3544 0.9102 0.030 Uiso 1 1 calc R . .
C12 C 1.2145(6) 0.1689(5) 0.9278(5) 0.0212(12) Uani 1 1 d . . .
C13 C 1.3349(6) 0.1974(5) 0.8171(5) 0.0217(12) Uani 1 1 d . . .
C14 C 1.5625(6) 0.1522(5) 0.6942(5) 0.0279(13) Uani 1 1 d . . .
H14A H 1.5764 0.1046 0.6416 0.033 Uiso 1 1 calc R . .
H14B H 1.6644 0.1476 0.7175 0.033 Uiso 1 1 calc R . .
C15 C 1.4920(6) 0.2917(6) 0.6273(5) 0.0314(14) Uani 1 1 d . . .
H15A H 1.5688 0.3521 0.6057 0.038 Uiso 1 1 calc R . .
H15B H 1.4572 0.3056 0.5494 0.038 Uiso 1 1 calc R . .
C16 C 1.2424(6) 0.4218(5) 0.6746(5) 0.0253(12) Uani 1 1 d . . .
H16A H 1.1399 0.4017 0.7285 0.030 Uiso 1 1 calc R . .
H16B H 1.2313 0.4400 0.5882 0.030 Uiso 1 1 calc R . .
C17 C 1.2838(6) 0.5416(5) 0.6736(5) 0.0231(12) Uani 1 1 d . . .
C18 C 1.4177(6) 0.5442(6) 0.7142(5) 0.0250(12) Uani 1 1 d . . .
H18 H 1.4866 0.4673 0.7475 0.030 Uiso 1 1 calc R . .
C19 C 1.4497(6) 0.6591(6) 0.7057(5) 0.0285(13) Uani 1 1 d . . .
H19 H 1.5409 0.6614 0.7330 0.034 Uiso 1 1 calc R . .
C20 C 1.3490(6) 0.7702(6) 0.6575(5) 0.0280(13) Uani 1 1 d . . .
H20 H 1.3694 0.8500 0.6506 0.034 Uiso 1 1 calc R . .
C21 C 1.2165(6) 0.7618(6) 0.6191(5) 0.0252(12) Uani 1 1 d . . .
H21 H 1.1460 0.8377 0.5860 0.030 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 N3 1.986(4) . ?
Cu1 O2 1.989(4) . ?
Cu1 O3 2.492(4) . ?
Cu1 Br2' 2.192(13) . ?
Cu1 Br2 2.4035(9) . ?
Cu1 Br1 2.4097(8) . ?
Br2 Br2' 1.042(16) . ?
O1 N4 1.228(6) . ?
O2 N4 1.301(6) . ?
O3 N4 1.233(6) . ?
N1 C13 1.346(7) . ?
N1 C1 1.397(7) . ?
N1 C14 1.476(6) . ?
N2 C13 1.328(7) . ?
N2 C16 1.448(7) . ?
N2 C15 1.484(7) . ?
N3 C21 1.347(7) . ?
N3 C17 1.350(7) . ?
C1 C2 1.411(8) . ?
C1 C6 1.411(7) . ?
C2 C3 1.368(8) . ?
C3 C4 1.390(8) . ?
C4 C5 1.385(8) . ?
C5 C6 1.410(8) . ?
C6 C7 1.462(7) . ?
C7 C8 1.409(7) . ?
C7 C12 1.413(8) . ?
C8 C9 1.375(8) . ?
C9 C10 1.395(8) . ?
C10 C11 1.372(8) . ?
C11 C12 1.413(7) . ?
C12 C13 1.455(7) . ?
C14 C15 1.524(8) . ?
C16 C17 1.513(8) . ?
C17 C18 1.393(7) . ?
C18 C19 1.383(8) . ?
C19 C20 1.378(8) . ?
C20 C21 1.392(7) . ?

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
N3 Cu1 O2 160.88(18) . . ?
N3 Cu1 Br2' 88.0(4) . . ?
O2 Cu1 Br2' 88.4(4) . . ?
N3 Cu1 Br2 90.64(12) . . ?
O2 Cu1 Br2 94.22(12) . . ?
Br2' Cu1 Br2 25.7(4) . . ?
N3 Cu1 Br1 92.79(12) . . ?
O2 Cu1 Br1 90.14(12) . . ?
Br2' Cu1 Br1 177.7(4) . . ?
Br2 Cu1 Br1 156.40(4) . . ?
Br2' Br2 Cu1 65.7(7) . . ?
Br2 Br2' Cu1 88.6(8) . . ?
N4 O2 Cu1 103.4(3) . . ?
C13 N1 C1 124.6(4) . . ?
C13 N1 C14 111.0(4) . . ?
C1 N1 C14 124.0(4) . . ?
C13 N2 C16 127.6(4) . . ?
C13 N2 C15 109.6(4) . . ?
C16 N2 C15 118.0(4) . . ?
C21 N3 C17 119.4(4) . . ?
C21 N3 Cu1 116.2(3) . . ?
C17 N3 Cu1 124.3(4) . . ?
O1 N4 O3 124.6(5) . . ?
O1 N4 O2 117.4(4) . . ?
O3 N4 O2 117.8(4) . . ?
N1 C1 C2 121.2(5) . . ?
N1 C1 C6 117.7(5) . . ?
C2 C1 C6 121.0(5) . . ?
C3 C2 C1 119.4(5) . . ?
C2 C3 C4 121.1(5) . . ?
C5 C4 C3 119.6(6) . . ?
C4 C5 C6 121.6(5) . . ?
C5 C6 C1 117.1(5) . . ?
C5 C6 C7 123.9(5) . . ?
C1 C6 C7 119.0(5) . . ?
C8 C7 C12 118.5(5) . . ?
C8 C7 C6 121.1(5) . . ?
C12 C7 C6 120.3(4) . . ?
C9 C8 C7 120.4(5) . . ?
C8 C9 C10 120.9(5) . . ?
C11 C10 C9 120.2(5) . . ?
C10 C11 C12 119.9(5) . . ?
C7 C12 C11 120.0(5) . . ?
C7 C12 C13 117.4(5) . . ?
C11 C12 C13 122.4(5) . . ?
N2 C13 N1 111.9(4) . . ?
N2 C13 C12 128.7(5) . . ?
N1 C13 C12 119.4(5) . . ?
N1 C14 C15 102.1(4) . . ?
N2 C15 C14 104.4(4) . . ?
N2 C16 C17 113.6(4) . . ?
N3 C17 C18 120.5(5) . . ?
N3 C17 C16 116.0(4) . . ?
C18 C17 C16 123.5(5) . . ?
C19 C18 C17 119.7(5) . . ?
C20 C19 C18 119.9(5) . . ?
C19 C20 C21 118.0(6) . . ?
N3 C21 C20 122.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         2.23
_refine_diff_density_min         -0.65
_refine_diff_density_rms         0.12

# Attachment 'compound3.cif'

data_ys03701
_database_code_depnum_ccdc_archive 'CCDC 678281'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 Br3 Cu N3'
_chemical_formula_weight         615.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
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'

_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                   11.867(4)
_cell_length_b                   13.477(5)
_cell_length_c                   14.980(5)
_cell_angle_alpha                106.773(8)
_cell_angle_beta                 104.342(8)
_cell_angle_gamma                100.370(8)
_cell_volume                     2139.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1012
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      21.9

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1196
_exptl_absorpt_coefficient_mu    6.637
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2773
_exptl_absorpt_correction_T_max  0.6915
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex CCD'
_diffrn_measurement_method       'ω & π'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            5690
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0952
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         23.00
_reflns_number_total             4038
_reflns_number_gt                2906
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex
_computing_cell_refinement       Apex
_computing_data_reduction        Apex
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Wingx

_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)+(0.1403P)²+38.0577P] 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     SHELXL
_refine_ls_extinction_coef       none
_refine_ls_extinction_expression none
_refine_ls_number_reflns         4038
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_ref         0.2489
_refine_ls_wR_factor_gt          0.2231
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.7934(2) 0.25910(19) 0.72892(18) 0.0214(8) Uani 1 1 d . . .
Cu2 Cu 0.5246(2) 0.6016(2) 0.80023(18) 0.0193(8) Uani 1 1 d . . .
Br1 Br 0.90607(19) 0.38593(18) 0.67788(17) 0.0326(8) Uani 1 1 d . . .
Br2 Br 0.76573(17) 0.06945(16) 0.69546(16) 0.0245(7) Uani 1 1 d . . .
Br3 Br 0.59272(17) 0.25763(17) 0.65377(16) 0.0261(7) Uani 1 1 d . . .
Br4 Br 0.70240(17) 0.72114(17) 0.80093(16) 0.0261(7) Uani 1 1 d . . .
Br5 Br 0.61006(18) 0.50996(17) 0.89779(16) 0.0266(7) Uani 1 1 d . . .
Br6 Br 0.35882(19) 0.62898(18) 0.86028(17) 0.0281(7) Uani 1 1 d . . .
N1 N 1.3448(13) 0.1823(12) 0.8699(11) 0.017(4) Uiso 1 1 d . . .
N2 N 1.1882(13) 0.2519(12) 0.8591(11) 0.015(4) Uiso 1 1 d . . .
N3 N 0.9012(14) 0.3105(13) 0.8704(12) 0.019(4) Uiso 1 1 d . . .
N4 N 0.3063(13) 0.9414(12) 0.6018(11) 0.017(4) Uiso 1 1 d . . .
N5 N 0.3729(13) 0.8059(12) 0.6231(11) 0.015(4) Uiso 1 1 d . . .
N6 N 0.4326(14) 0.5551(13) 0.6556(12) 0.023(4) Uiso 1 1 d . . .
C1 C 1.4124(16) 0.1077(15) 0.8763(14) 0.016(5) Uiso 1 1 d . . .
C2 C 1.532(2) 0.133(2) 0.8776(17) 0.037(6) Uiso 1 1 d . . .
H2 H 1.5686 0.2003 0.8772 0.044 Uiso 1 1 calc R . .
C3 C 1.594(2) 0.058(2) 0.8795(18) 0.045(7) Uiso 1 1 d . . .
H3 H 1.6735 0.0730 0.8795 0.054 Uiso 1 1 calc R . .
C4 C 1.540(2) -0.0432(19) 0.8814(16) 0.035(6) Uiso 1 1 d . . .
H4 H 1.5836 -0.0933 0.8852 0.042 Uiso 1 1 calc R . .
C5 C 1.4247(18) -0.0652(18) 0.8776(15) 0.028(5) Uiso 1 1 d . . .
H5 H 1.3887 -0.1333 0.8760 0.034 Uiso 1 1 calc R . .
C6 C 1.3532(18) 0.0083(17) 0.8758(15) 0.024(5) Uiso 1 1 d . . .
C7 C 1.2314(16) -0.0125(15) 0.8796(14) 0.016(5) Uiso 1 1 d . . .
C8 C 1.1682(18) -0.1059(17) 0.8874(15) 0.025(5) Uiso 1 1 d . . .
H8 H 1.2074 -0.1592 0.8909 0.030 Uiso 1 1 calc R . .
C9 C 1.055(2) -0.1234(19) 0.8902(16) 0.034(6) Uiso 1 1 d . . .
H9 H 1.0181 -0.1883 0.8938 0.040 Uiso 1 1 calc R . .
C10 C 0.9919(19) -0.0449(17) 0.8877(15) 0.028(6) Uiso 1 1 d . . .
H10 H 0.9133 -0.0562 0.8904 0.034 Uiso 1 1 calc R . .
C11 C 1.0521(18) 0.0515(17) 0.8808(15) 0.025(5) Uiso 1 1 d . . .
H11 H 1.0134 0.1057 0.8813 0.030 Uiso 1 1 calc R . .
C12 C 1.1684(15) 0.0677(14) 0.8734(13) 0.011(4) Uiso 1 1 d . . .
C13 C 1.2295(17) 0.1659(16) 0.8664(14) 0.019(5) Uiso 1 1 d . . .
C14 C 1.3957(17) 0.2898(16) 0.8706(15) 0.022(5) Uiso 1 1 d . . .
H14A H 1.4365 0.2864 0.8215 0.026 Uiso 1 1 calc R . .
H14B H 1.4521 0.3353 0.9347 0.026 Uiso 1 1 calc R . .
C15 C 1.2849(17) 0.3302(16) 0.8459(16) 0.023(5) Uiso 1 1 d . . .
H15A H 1.2982 0.4028 0.8902 0.027 Uiso 1 1 calc R . .
H15B H 1.2635 0.3293 0.7788 0.027 Uiso 1 1 calc R . .
C16 C 1.0623(16) 0.2534(16) 0.8255(14) 0.017(5) Uiso 1 1 d . . .
H16A H 1.0134 0.1797 0.7899 0.021 Uiso 1 1 calc R . .
H16B H 1.0548 0.2913 0.7793 0.021 Uiso 1 1 calc R . .
C17 C 1.0096(17) 0.3042(16) 0.9039(14) 0.020(5) Uiso 1 1 d . . .
C18 C 1.0760(17) 0.3433(15) 1.0053(14) 0.018(5) Uiso 1 1 d . . .
H18 H 1.1542 0.3374 1.0272 0.022 Uiso 1 1 calc R . .
C19 C 1.0206(17) 0.3903(16) 1.0700(16) 0.023(5) Uiso 1 1 d . . .
H19 H 1.0607 0.4159 1.1373 0.027 Uiso 1 1 calc R . .
C20 C 0.9052(19) 0.3993(17) 1.0347(16) 0.029(5) Uiso 1 1 d . . .
H20 H 0.8669 0.4325 1.0773 0.034 Uiso 1 1 calc R . .
C21 C 0.8468(17) 0.3562(15) 0.9313(14) 0.014(4) Uiso 1 1 d . . .
H21 H 0.7685 0.3602 0.9061 0.017 Uiso 1 1 calc R . .
C22 C 0.2325(17) 1.0131(16) 0.6011(14) 0.019(5) Uiso 1 1 d . . .
C23 C 0.2675(18) 1.1047(16) 0.5816(15) 0.023(5) Uiso 1 1 d . . .
H23 H 0.3397 1.1203 0.5679 0.028 Uiso 1 1 calc R . .
C24 C 0.1958(19) 1.1729(18) 0.5822(16) 0.031(6) Uiso 1 1 d . . .
H24 H 0.2184 1.2354 0.5689 0.038 Uiso 1 1 calc R . .
C25 C 0.0891(18) 1.1485(17) 0.6030(15) 0.023(5) Uiso 1 1 d . . .
H25 H 0.0407 1.1958 0.6050 0.028 Uiso 1 1 calc R . .
C26 C 0.0534(18) 1.0535(16) 0.6210(14) 0.021(5) Uiso 1 1 d . . .
H26 H -0.0193 1.0367 0.6335 0.025 Uiso 1 1 calc R . .
C27 C 0.1248(17) 0.9866(16) 0.6200(14) 0.017(5) Uiso 1 1 d . . .
C28 C 0.0885(17) 0.8784(16) 0.6302(15) 0.021(5) Uiso 1 1 d . . .
C29 C -0.0228(19) 0.8444(17) 0.6456(15) 0.027(5) Uiso 1 1 d . . .
H29 H -0.0722 0.8906 0.6517 0.033 Uiso 1 1 calc R . .
C30 C -0.0587(19) 0.7461(16) 0.6516(15) 0.025(5) Uiso 1 1 d . . .
H30 H -0.1308 0.7261 0.6641 0.031 Uiso 1 1 calc R . .
C31 C 0.0125(18) 0.6753(17) 0.6390(15) 0.026(5) Uiso 1 1 d . . .
H31 H -0.0154 0.6062 0.6389 0.031 Uiso 1 1 calc R . .
C32 C 0.1219(17) 0.7046(16) 0.6270(14) 0.020(5) Uiso 1 1 d . . .
H32 H 0.1683 0.6560 0.6184 0.024 Uiso 1 1 calc R . .
C33 C 0.1655(18) 0.8132(16) 0.6276(15) 0.023(5) Uiso 1 1 d . . .
C34 C 0.2803(18) 0.8477(17) 0.6185(15) 0.024(5) Uiso 1 1 d . . .
C35 C 0.4275(17) 0.9581(16) 0.5849(15) 0.021(5) Uiso 1 1 d . . .
H35A H 0.4184 0.9507 0.5169 0.025 Uiso 1 1 calc R . .
H35B H 0.4803 1.0287 0.6272 0.025 Uiso 1 1 calc R . .
C36 C 0.4754(18) 0.8722(17) 0.6097(16) 0.026(5) Uiso 1 1 d . . .
H36A H 0.4998 0.8307 0.5568 0.031 Uiso 1 1 calc R . .
H36B H 0.5439 0.9020 0.6696 0.031 Uiso 1 1 calc R . .
C37 C 0.3994(18) 0.7310(16) 0.6767(15) 0.024(5) Uiso 1 1 d . . .
H37A H 0.3447 0.7264 0.7149 0.028 Uiso 1 1 calc R . .
H37B H 0.4811 0.7603 0.7223 0.028 Uiso 1 1 calc R . .
C38 C 0.3865(18) 0.6166(16) 0.6075(15) 0.023(5) Uiso 1 1 d . . .
C39 C 0.3324(15) 0.5807(14) 0.5082(12) 0.008(4) Uiso 1 1 d . . .
H39 H 0.3024 0.6259 0.4777 0.009 Uiso 1 1 calc R . .
C40 C 0.3230(16) 0.4753(15) 0.4535(15) 0.017(5) Uiso 1 1 d . . .
H40 H 0.2856 0.4479 0.3857 0.021 Uiso 1 1 calc R . .
C41 C 0.3707(18) 0.4120(18) 0.5024(16) 0.028(6) Uiso 1 1 d . . .
H41 H 0.3669 0.3415 0.4676 0.034 Uiso 1 1 calc R . .
C42 C 0.4242(17) 0.4543(16) 0.6039(14) 0.019(5) Uiso 1 1 d . . .
H42 H 0.4548 0.4109 0.6364 0.023 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 N3 2.024(15) . ?
Cu1 Br3 2.363(3) . ?
Cu1 Br1 2.394(3) . ?
Cu1 Br2 2.402(3) . ?
Cu2 N6 2.019(16) . ?
Cu2 Br5 2.334(3) . ?
Cu2 Br6 2.400(4) . ?
Cu2 Br4 2.409(3) . ?
N1 C13 1.33(2) . ?
N1 C1 1.40(3) . ?
N1 C14 1.46(2) . ?
N2 C13 1.36(2) . ?
N2 C16 1.46(2) . ?
N2 C15 1.51(2) . ?
N3 C17 1.29(2) . ?
N3 C21 1.32(2) . ?
N4 C34 1.35(3) . ?
N4 C22 1.42(3) . ?
N4 C35 1.51(2) . ?
N5 C34 1.32(3) . ?
N5 C36 1.47(2) . ?
N5 C37 1.49(3) . ?
N6 C42 1.33(3) . ?
N6 C38 1.35(3) . ?
C1 C2 1.39(3) . ?
C1 C6 1.39(3) . ?
C2 C3 1.36(3) . ?
C3 C4 1.41(3) . ?
C4 C5 1.33(3) . ?
C5 C6 1.42(3) . ?
C6 C7 1.44(3) . ?
C7 C8 1.40(3) . ?
C7 C12 1.43(3) . ?
C8 C9 1.33(3) . ?
C9 C10 1.41(3) . ?
C10 C11 1.41(3) . ?
C11 C12 1.39(3) . ?
C12 C13 1.44(3) . ?
C14 C15 1.51(3) . ?
C16 C17 1.51(3) . ?
C17 C18 1.41(3) . ?
C18 C19 1.37(3) . ?
C19 C20 1.38(3) . ?
C20 C21 1.42(3) . ?
C22 C23 1.37(3) . ?
C22 C27 1.38(3) . ?
C23 C24 1.36(3) . ?
C24 C25 1.38(3) . ?
C25 C26 1.40(3) . ?
C26 C27 1.34(3) . ?
C27 C28 1.51(3) . ?
C28 C33 1.38(3) . ?
C28 C29 1.41(3) . ?
C29 C30 1.35(3) . ?
C30 C31 1.39(3) . ?
C31 C32 1.36(3) . ?
C32 C33 1.46(3) . ?
C33 C34 1.41(3) . ?
C35 C36 1.48(3) . ?
C37 C38 1.55(3) . ?
C38 C39 1.36(3) . ?
C39 C40 1.39(3) . ?
C40 C41 1.38(3) . ?
C41 C42 1.39(3) . ?

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
N3 Cu1 Br3 133.6(5) . . ?
N3 Cu1 Br1 97.6(4) . . ?
Br3 Cu1 Br1 101.69(12) . . ?
N3 Cu1 Br2 97.5(5) . . ?
Br3 Cu1 Br2 99.33(10) . . ?
Br1 Cu1 Br2 133.01(15) . . ?
N6 Cu2 Br5 132.7(5) . . ?
N6 Cu2 Br6 97.1(5) . . ?
Br5 Cu2 Br6 100.18(12) . . ?
N6 Cu2 Br4 97.5(5) . . ?
Br5 Cu2 Br4 101.28(12) . . ?
Br6 Cu2 Br4 133.79(14) . . ?
C13 N1 C1 124.6(16) . . ?
C13 N1 C14 112.1(17) . . ?
C1 N1 C14 123.2(15) . . ?
C13 N2 C16 126.9(15) . . ?
C13 N2 C15 108.3(15) . . ?
C16 N2 C15 119.7(16) . . ?
C17 N3 C21 120.2(17) . . ?
C17 N3 Cu1 128.6(15) . . ?
C21 N3 Cu1 111.2(12) . . ?
C34 N4 C22 125.7(17) . . ?
C34 N4 C35 109.1(17) . . ?
C22 N4 C35 125.2(15) . . ?
C34 N5 C36 112.8(17) . . ?
C34 N5 C37 125.0(18) . . ?
C36 N5 C37 117.3(16) . . ?
C42 N6 C38 118.4(18) . . ?
C42 N6 Cu2 114.5(14) . . ?
C38 N6 Cu2 127.0(14) . . ?
C2 C1 C6 123(2) . . ?
C2 C1 N1 119.3(18) . . ?
C6 C1 N1 117.4(17) . . ?
C3 C2 C1 118(2) . . ?
C2 C3 C4 121(2) . . ?
C5 C4 C3 119(2) . . ?
C4 C5 C6 124(2) . . ?
C1 C6 C5 114.7(19) . . ?
C1 C6 C7 121(2) . . ?
C5 C6 C7 124.1(19) . . ?
C8 C7 C12 116.8(18) . . ?
C8 C7 C6 125(2) . . ?
C12 C7 C6 118.0(17) . . ?
C9 C8 C7 124(2) . . ?
C8 C9 C10 121(2) . . ?
C9 C10 C11 117(2) . . ?
C12 C11 C10 122(2) . . ?
C11 C12 C7 119.2(17) . . ?
C11 C12 C13 121.6(19) . . ?
C7 C12 C13 119.1(17) . . ?
N1 C13 N2 111.1(16) . . ?
N1 C13 C12 119.4(19) . . ?
N2 C13 C12 129.5(18) . . ?
N1 C14 C15 102.7(15) . . ?
N2 C15 C14 103.7(16) . . ?
N2 C16 C17 116.7(16) . . ?
N3 C17 C18 123(2) . . ?
N3 C17 C16 114.5(17) . . ?
C18 C17 C16 122.1(18) . . ?
C19 C18 C17 117(2) . . ?
C18 C19 C20 120(2) . . ?
C19 C20 C21 118(2) . . ?
N3 C21 C20 121.4(19) . . ?
C23 C22 C27 122(2) . . ?
C23 C22 N4 120.3(19) . . ?
C27 C22 N4 117.9(18) . . ?
C24 C23 C22 119(2) . . ?
C23 C24 C25 119(2) . . ?
C24 C25 C26 121(2) . . ?
C27 C26 C25 120(2) . . ?
C26 C27 C22 119.3(19) . . ?
C26 C27 C28 123.0(19) . . ?
C22 C27 C28 118(2) . . ?
C33 C28 C29 119.5(19) . . ?
C33 C28 C27 120.0(19) . . ?
C29 C28 C27 120(2) . . ?
C30 C29 C28 121(2) . . ?
C29 C30 C31 120(2) . . ?
C32 C31 C30 122(2) . . ?
C31 C32 C33 119(2) . . ?
C28 C33 C34 120.8(19) . . ?
C28 C33 C32 118.2(19) . . ?
C34 C33 C32 121(2) . . ?
N5 C34 N4 110.0(18) . . ?
N5 C34 C33 132(2) . . ?
N4 C34 C33 118(2) . . ?
C36 C35 N4 103.8(15) . . ?
N5 C36 C35 103.4(16) . . ?
N5 C37 C38 113.0(17) . . ?
N6 C38 C39 123.3(19) . . ?
N6 C38 C37 113.1(17) . . ?
C39 C38 C37 123.7(19) . . ?
C38 C39 C40 118.7(19) . . ?
C41 C40 C39 118.2(19) . . ?
C40 C41 C42 120(2) . . ?
N6 C42 C41 122(2) . . ?

_diffrn_measured_fraction_theta_max 0.678
_diffrn_reflns_theta_full        23.00
_diffrn_measured_fraction_theta_full 0.678
_refine_diff_density_max         2.21
_refine_diff_density_min         -0.94
_refine_diff_density_rms         0.26

# Attachment 'compound4.cif'

data_ys02801
_database_code_depnum_ccdc_archive 'CCDC 678282'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H36 Cu2 N24'
_chemical_formula_weight         1004.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   31.917(2)
_cell_length_b                   8.5868(5)
_cell_length_c                   15.9626(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.844(2)
_cell_angle_gamma                90.00
_cell_volume                     4164.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3049
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      23.7

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2056
_exptl_absorpt_coefficient_mu    1.089
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7502
_exptl_absorpt_correction_T_max  0.8989
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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 Apex CCD'
_diffrn_measurement_method       'ω & π'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            18504
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.78
_reflns_number_total             3981
_reflns_number_gt                2959
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex
_computing_cell_refinement       Apex
_computing_data_reduction        Apex
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Wingx

_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)+(0.0327P)²+5.7482P] 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       none
_refine_ls_number_reflns         3981
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Cu Cu 0.041069(11) 0.10693(4) 0.21529(2) 0.01452(12) Uani 1 1 d . . .
N1 N 0.18347(7) -0.4411(3) 0.47129(15) 0.0145(5) Uani 1 1 d . . .
N2 N 0.12194(8) -0.3178(3) 0.40264(15) 0.0156(5) Uani 1 1 d . . .
N3 N 0.04306(8) -0.1586(3) 0.20118(15) 0.0150(5) Uani 1 1 d . . .
N4 N 0.02654(7) 0.1071(3) 0.33034(15) 0.0146(5) Uani 1 1 d . . .
N5 N 0.04570(8) 0.1963(3) 0.38948(16) 0.0188(6) Uani 1 1 d . . .
N6 N 0.06395(9) 0.2777(3) 0.44573(18) 0.0304(7) Uani 1 1 d . . .
N7 N 0.04467(8) 0.1433(3) 0.09473(16) 0.0194(6) Uani 1 1 d . . .
N8 N 0.07507(9) 0.0840(3) 0.07651(16) 0.0194(6) Uani 1 1 d . . .
N9 N 0.10357(9) 0.0286(3) 0.05623(18) 0.0293(7) Uani 1 1 d . . .
N10 N 0.10195(8) 0.1774(3) 0.27567(16) 0.0244(6) Uani 1 1 d . . .
N11 N 0.12345(8) 0.2543(3) 0.24114(16) 0.0205(6) Uani 1 1 d . . .
N12 N 0.14560(9) 0.3294(3) 0.21099(19) 0.0316(7) Uani 1 1 d . . .
C1 C 0.22771(9) -0.4830(3) 0.49431(19) 0.0156(7) Uani 1 1 d . . .
C2 C 0.24590(10) -0.5814(3) 0.56584(19) 0.0174(7) Uani 1 1 d . . .
H2 H 0.2280 -0.6226 0.5983 0.021 Uiso 1 1 calc R . .
C3 C 0.28992(10) -0.6187(3) 0.5892(2) 0.0209(7) Uani 1 1 d . . .
H3 H 0.3024 -0.6857 0.6378 0.025 Uiso 1 1 calc R . .
C4 C 0.31636(10) -0.5585(3) 0.5416(2) 0.0203(7) Uani 1 1 d . . .
H4 H 0.3467 -0.5850 0.5577 0.024 Uiso 1 1 calc R . .
C5 C 0.29846(9) -0.4609(3) 0.47140(19) 0.0178(7) Uani 1 1 d . . .
H5 H 0.3169 -0.4195 0.4401 0.021 Uiso 1 1 calc R . .
C6 C 0.25356(9) -0.4207(3) 0.44478(18) 0.0153(7) Uani 1 1 d . . .
C7 C 0.23231(9) -0.3233(3) 0.36829(18) 0.0147(6) Uani 1 1 d . . .
C8 C 0.25640(10) -0.2623(3) 0.31502(19) 0.0184(7) Uani 1 1 d . . .
H8 H 0.2872 -0.2795 0.3308 0.022 Uiso 1 1 calc R . .
C9 C 0.23572(10) -0.1781(3) 0.2406(2) 0.0221(7) Uani 1 1 d . . .
H9 H 0.2526 -0.1356 0.2063 0.027 Uiso 1 1 calc R . .
C10 C 0.19060(11) -0.1546(4) 0.2148(2) 0.0250(8) Uani 1 1 d . . .
H10 H 0.1765 -0.1003 0.1619 0.030 Uiso 1 1 calc R . .
C11 C 0.16629(10) -0.2101(3) 0.26625(19) 0.0207(7) Uani 1 1 d . . .
H11 H 0.1354 -0.1935 0.2486 0.025 Uiso 1 1 calc R . .
C12 C 0.18665(9) -0.2911(3) 0.34454(18) 0.0159(7) Uani 1 1 d . . .
C13 C 0.16311(9) -0.3473(3) 0.40356(18) 0.0127(6) Uani 1 1 d . . .
C14 C 0.15272(9) -0.4940(3) 0.51886(19) 0.0188(7) Uani 1 1 d . . .
H14A H 0.1651 -0.4759 0.5830 0.023 Uiso 1 1 calc R . .
H14B H 0.1455 -0.6058 0.5081 0.023 Uiso 1 1 calc R . .
C15 C 0.11258(9) -0.3918(3) 0.47860(19) 0.0183(7) Uani 1 1 d . . .
H15A H 0.0854 -0.4552 0.4592 0.022 Uiso 1 1 calc R . .
H15B H 0.1093 -0.3126 0.5212 0.022 Uiso 1 1 calc R . .
C16 C 0.09039(9) -0.2053(3) 0.34923(18) 0.0154(6) Uani 1 1 d . . .
H16A H 0.1067 -0.1127 0.3392 0.018 Uiso 1 1 calc R . .
H16B H 0.0706 -0.1709 0.3827 0.018 Uiso 1 1 calc R . .
C17 C 0.06271(9) -0.2681(3) 0.26096(18) 0.0144(6) Uani 1 1 d . . .
C18 C 0.05832(10) -0.4263(3) 0.2421(2) 0.0206(7) Uani 1 1 d . . .
H18 H 0.0725 -0.5009 0.2855 0.025 Uiso 1 1 calc R . .
C19 C 0.03292(10) -0.4740(4) 0.1587(2) 0.0232(7) Uani 1 1 d . . .
H19 H 0.0296 -0.5815 0.1440 0.028 Uiso 1 1 calc R . .
C20 C 0.01269(10) -0.3621(3) 0.09765(19) 0.0202(7) Uani 1 1 d . . .
H20 H -0.0049 -0.3912 0.0402 0.024 Uiso 1 1 calc R . .
C21 C 0.01844(9) -0.2069(3) 0.12135(19) 0.0165(7) Uani 1 1 d . . .
H21 H 0.0043 -0.1307 0.0790 0.020 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
Cu N10 1.981(3) . ?
Cu N7 1.987(2) . ?
Cu N4 2.027(2) . ?
Cu N4 2.055(2) 2 ?
Cu N3 2.294(2) . ?
N1 C13 1.345(3) . ?
N1 C1 1.393(4) . ?
N1 C14 1.484(3) . ?
N2 C13 1.334(3) . ?
N2 C16 1.465(3) . ?
N2 C15 1.479(3) . ?
N3 C21 1.342(4) . ?
N3 C17 1.350(4) . ?
N4 N5 1.224(3) . ?
N4 Cu 2.055(2) 2 ?
N5 N6 1.146(3) . ?
N7 N8 1.207(3) . ?
N8 N9 1.157(3) . ?
N10 N11 1.201(3) . ?
N11 N12 1.164(3) . ?
C1 C2 1.396(4) . ?
C1 C6 1.411(4) . ?
C2 C3 1.376(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.407(4) . ?
C6 C7 1.464(4) . ?
C7 C8 1.410(4) . ?
C7 C12 1.416(4) . ?
C8 C9 1.375(4) . ?
C9 C10 1.386(4) . ?
C10 C11 1.376(4) . ?
C11 C12 1.403(4) . ?
C12 C13 1.456(4) . ?
C14 C15 1.523(4) . ?
C16 C17 1.514(4) . ?
C17 C18 1.389(4) . ?
C18 C19 1.392(4) . ?
C19 C20 1.380(4) . ?
C20 C21 1.382(4) . ?

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
N10 Cu N7 94.82(10) . . ?
N10 Cu N4 91.23(10) . . ?
N7 Cu N4 166.98(10) . . ?
N10 Cu N4 159.90(10) . 2 ?
N7 Cu N4 91.30(10) . 2 ?
N4 Cu N4 79.30(10) . 2 ?
N10 Cu N3 107.40(10) . . ?
N7 Cu N3 92.83(9) . . ?
N4 Cu N3 96.35(9) . . ?
N4 Cu N3 91.36(9) 2 . ?
C13 N1 C1 124.6(2) . . ?
C13 N1 C14 111.2(2) . . ?
C1 N1 C14 124.2(2) . . ?
C13 N2 C16 129.1(2) . . ?
C13 N2 C15 110.8(2) . . ?
C16 N2 C15 119.0(2) . . ?
C21 N3 C17 117.8(2) . . ?
C21 N3 Cu 112.03(18) . . ?
C17 N3 Cu 130.10(19) . . ?
N5 N4 Cu 120.01(19) . . ?
N5 N4 Cu 119.74(19) . 2 ?
Cu N4 Cu 100.70(10) . 2 ?
N6 N5 N4 178.8(3) . . ?
N8 N7 Cu 117.15(19) . . ?
N9 N8 N7 177.8(3) . . ?
N11 N10 Cu 123.9(2) . . ?
N12 N11 N10 177.2(3) . . ?
N1 C1 C2 120.4(3) . . ?
N1 C1 C6 118.3(3) . . ?
C2 C1 C6 121.3(3) . . ?
C3 C2 C1 119.8(3) . . ?
C2 C3 C4 120.3(3) . . ?
C5 C4 C3 120.0(3) . . ?
C4 C5 C6 121.7(3) . . ?
C5 C6 C1 117.0(3) . . ?
C5 C6 C7 124.1(3) . . ?
C1 C6 C7 118.9(3) . . ?
C8 C7 C12 118.2(3) . . ?
C8 C7 C6 121.1(3) . . ?
C12 C7 C6 120.7(3) . . ?
C9 C8 C7 120.7(3) . . ?
C8 C9 C10 120.9(3) . . ?
C11 C10 C9 119.8(3) . . ?
C10 C11 C12 120.7(3) . . ?
C11 C12 C7 119.5(3) . . ?
C11 C12 C13 123.4(3) . . ?
C7 C12 C13 117.1(3) . . ?
N2 C13 N1 110.8(2) . . ?
N2 C13 C12 129.2(3) . . ?
N1 C13 C12 120.1(2) . . ?
N1 C14 C15 102.1(2) . . ?
N2 C15 C14 103.8(2) . . ?
N2 C16 C17 114.1(2) . . ?
N3 C17 C18 122.3(3) . . ?
N3 C17 C16 115.0(2) . . ?
C18 C17 C16 122.8(3) . . ?
C17 C18 C19 119.1(3) . . ?
C20 C19 C18 118.7(3) . . ?
C19 C20 C21 118.9(3) . . ?
N3 C21 C20 123.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.78
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.63
_refine_diff_density_min         -0.44
_refine_diff_density_rms         0.08

# Attachment 'compound5.cif'

data_ys05701
_database_code_depnum_ccdc_archive 'CCDC 678283'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C48 H42 Cu2 N10 O2 S4), (C H4 O)'
_chemical_formula_sum            'C49 H46 Cu2 N10 O3 S4'
_chemical_formula_weight         1078.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
S S 0.1246 0.1234 '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'
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'

_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                   9.2344(7)
_cell_length_b                   11.5240(9)
_cell_length_c                   12.4542(9)
_cell_angle_alpha                65.526(3)
_cell_angle_beta                 88.615(3)
_cell_angle_gamma                80.281(3)
_cell_volume                     1187.40(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3830
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      24

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    1.126
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7660
_exptl_absorpt_correction_T_max  0.8767
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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 Apex CCD'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            18035
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         24.20
_reflns_number_total             3771
_reflns_number_gt                2813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex
_computing_cell_refinement       Apex
_computing_data_reduction        Apex
_computing_structure_solution    'SHELXS-97 (sHELDRICK, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Wingx

_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)+(0.0508P)²+2.3353P] 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       none
_refine_ls_number_reflns         3771
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Cu Cu 0.47309(6) 0.93199(5) 0.92342(5) 0.03164(19) Uani 1 1 d . . .
N1 N 0.7641(4) 0.3674(3) 1.3554(3) 0.0275(8) Uani 1 1 d . . .
N2 N 0.6536(4) 0.5299(3) 1.1972(3) 0.0258(8) Uani 1 1 d . . .
N3 N 0.6135(4) 0.7919(3) 0.8953(3) 0.0258(8) Uani 1 1 d . . .
N4 N 0.3063(4) 0.8601(4) 0.8992(4) 0.0416(10) Uani 1 1 d . . .
N5 N 0.4797(5) 1.0901(5) 0.7433(5) 0.086(2) Uani 1 1 d . . .
S1 S 0.07566(13) 0.75591(11) 0.85138(11) 0.0362(3) Uani 1 1 d . . .
S2 S 0.47672(12) 1.34995(11) 0.59952(11) 0.0339(3) Uani 1 1 d . . .
O O 0.3667(3) 1.0327(3) 1.0022(3) 0.0379(8) Uani 1 1 d . . .
O1 O 0.4295(5) 0.0213(5) 0.5121(4) 0.0661(14) Uani 0.50 1 d P . .
C C 0.4295(5) 0.0213(5) 0.5121(4) 0.0661(14) Uani 0.50 1 d P . .
C1 C 0.8724(5) 0.2911(4) 1.4452(4) 0.0318(11) Uani 1 1 d . . .
C2 C 0.8540(6) 0.1674(5) 1.5262(4) 0.0437(13) Uani 1 1 d . . .
H2 H 0.7683 0.1344 1.5209 0.052 Uiso 1 1 calc R . .
C3 C 0.9616(6) 0.0944(5) 1.6136(4) 0.0539(16) Uani 1 1 d . . .
H3 H 0.9502 0.0101 1.6686 0.065 Uiso 1 1 calc R . .
C4 C 1.0875(6) 0.1432(6) 1.6221(4) 0.0502(15) Uani 1 1 d . . .
H4 H 1.1612 0.0922 1.6829 0.060 Uiso 1 1 calc R . .
C5 C 1.1051(5) 0.2651(5) 1.5426(4) 0.0404(13) Uani 1 1 d . . .
H5 H 1.1911 0.2973 1.5490 0.048 Uiso 1 1 calc R . .
C6 C 0.9971(5) 0.3428(4) 1.4517(4) 0.0294(11) Uani 1 1 d . . .
C7 C 1.0111(5) 0.4723(4) 1.3633(4) 0.0284(10) Uani 1 1 d . . .
C8 C 1.1351(5) 0.5289(5) 1.3635(4) 0.0336(11) Uani 1 1 d . . .
H8 H 1.2088 0.4847 1.4255 0.040 Uiso 1 1 calc R . .
C9 C 1.1516(5) 0.6463(5) 1.2761(4) 0.0371(12) Uani 1 1 d . . .
H9 H 1.2359 0.6826 1.2784 0.044 Uiso 1 1 calc R . .
C10 C 1.0451(5) 0.7126(5) 1.1841(4) 0.0367(12) Uani 1 1 d . . .
H10 H 1.0584 0.7927 1.1225 0.044 Uiso 1 1 calc R . .
C11 C 0.9213(5) 0.6626(5) 1.1821(4) 0.0331(11) Uani 1 1 d . . .
H11 H 0.8489 0.7089 1.1193 0.040 Uiso 1 1 calc R . .
C12 C 0.9000(5) 0.5439(4) 1.2714(4) 0.0266(10) Uani 1 1 d . . .
C13 C 0.7719(4) 0.4855(4) 1.2719(4) 0.0252(10) Uani 1 1 d . . .
C14 C 0.6331(5) 0.3192(4) 1.3354(4) 0.0337(11) Uani 1 1 d . . .
H14A H 0.5734 0.2931 1.4060 0.040 Uiso 1 1 calc R . .
H14B H 0.6611 0.2449 1.3140 0.040 Uiso 1 1 calc R . .
C15 C 0.5508(5) 0.4374(4) 1.2323(4) 0.0322(11) Uani 1 1 d . . .
H15A H 0.5283 0.4152 1.1665 0.039 Uiso 1 1 calc R . .
H15B H 0.4578 0.4732 1.2574 0.039 Uiso 1 1 calc R . .
C16 C 0.6029(5) 0.6588(4) 1.1048(3) 0.0244(10) Uani 1 1 d . . .
H16A H 0.6366 0.7237 1.1265 0.029 Uiso 1 1 calc R . .
H16B H 0.4940 0.6764 1.0995 0.029 Uiso 1 1 calc R . .
C17 C 0.6584(4) 0.6740(4) 0.9852(3) 0.0217(9) Uani 1 1 d . . .
C18 C 0.7493(4) 0.5761(4) 0.9671(4) 0.0280(10) Uani 1 1 d . . .
H18 H 0.7803 0.4945 1.0312 0.034 Uiso 1 1 calc R . .
C19 C 0.7949(5) 0.5985(5) 0.8543(4) 0.0365(12) Uani 1 1 d . . .
H19 H 0.8575 0.5324 0.8403 0.044 Uiso 1 1 calc R . .
C20 C 0.7482(5) 0.7181(5) 0.7626(4) 0.0389(13) Uani 1 1 d . . .
H20 H 0.7770 0.7353 0.6845 0.047 Uiso 1 1 calc R . .
C21 C 0.6594(5) 0.8115(5) 0.7866(4) 0.0358(12) Uani 1 1 d . . .
H21 H 0.6288 0.8941 0.7236 0.043 Uiso 1 1 calc R . .
C22 C 0.2110(5) 0.8161(4) 0.8792(4) 0.0284(10) Uani 1 1 d . . .
C23 C 0.4785(5) 1.1977(5) 0.6840(4) 0.0356(12) Uani 1 1 d . . .
C24 C 0.2318(5) 1.0079(5) 1.0567(5) 0.0478(14) Uani 1 1 d . . .
H24A H 0.1629 1.0017 1.0014 0.072 Uiso 1 1 calc R . .
H24B H 0.1899 1.0786 1.0786 0.072 Uiso 1 1 calc R . .
H24C H 0.2494 0.9261 1.1277 0.072 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
Cu O 1.946(3) . ?
Cu O 1.948(3) 2_677 ?
Cu N4 1.951(4) . ?
Cu N3 2.038(3) . ?
Cu N5 2.236(5) . ?
Cu Cu 3.0213(12) 2_677 ?
N1 C13 1.340(5) . ?
N1 C1 1.402(5) . ?
N1 C14 1.480(5) . ?
N2 C13 1.336(5) . ?
N2 C16 1.458(5) . ?
N2 C15 1.471(5) . ?
N3 C21 1.346(5) . ?
N3 C17 1.357(5) . ?
N4 C22 1.167(6) . ?
N5 C23 1.149(6) . ?
S1 C22 1.636(5) . ?
S2 C23 1.627(5) . ?
O C24 1.419(5) . ?
O Cu 1.948(3) 2_677 ?
O1 C 1.383(9) 2_656 ?
O1 O1 1.383(9) 2_656 ?
C1 C2 1.400(7) . ?
C1 C6 1.401(6) . ?
C2 C3 1.375(7) . ?
C3 C4 1.399(8) . ?
C4 C5 1.377(8) . ?
C5 C6 1.411(6) . ?
C6 C7 1.467(6) . ?
C7 C8 1.410(6) . ?
C7 C12 1.426(6) . ?
C8 C9 1.371(7) . ?
C9 C10 1.393(7) . ?
C10 C11 1.370(6) . ?
C11 C12 1.402(6) . ?
C12 C13 1.455(6) . ?
C14 C15 1.527(6) . ?
C16 C17 1.512(5) . ?
C17 C18 1.382(6) . ?
C18 C19 1.387(6) . ?
C19 C20 1.382(7) . ?
C20 C21 1.370(7) . ?

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
O Cu O 78.22(13) . 2_677 ?
O Cu N4 96.33(15) . . ?
O Cu N4 162.30(16) 2_677 . ?
O Cu N3 161.29(14) . . ?
O Cu N3 90.56(13) 2_677 . ?
N4 Cu N3 89.87(15) . . ?
O Cu N5 99.54(19) . . ?
O Cu N5 97.18(19) 2_677 . ?
N4 Cu N5 100.3(2) . . ?
N3 Cu N5 96.66(19) . . ?
O Cu Cu 39.13(9) . 2_677 ?
O Cu Cu 39.10(9) 2_677 2_677 ?
N4 Cu Cu 133.25(12) . 2_677 ?
N3 Cu Cu 128.06(10) . 2_677 ?
N5 Cu Cu 100.80(19) . 2_677 ?
C13 N1 C1 125.2(4) . . ?
C13 N1 C14 111.9(3) . . ?
C1 N1 C14 122.7(4) . . ?
C13 N2 C16 130.0(4) . . ?
C13 N2 C15 111.2(3) . . ?
C16 N2 C15 117.7(3) . . ?
C21 N3 C17 118.2(4) . . ?
C21 N3 Cu 121.1(3) . . ?
C17 N3 Cu 120.6(3) . . ?
C22 N4 Cu 175.9(4) . . ?
C23 N5 Cu 149.5(6) . . ?
C24 O Cu 123.5(3) . . ?
C24 O Cu 122.6(3) . 2_677 ?
Cu O Cu 101.78(13) . 2_677 ?
C O1 O1 0.0(5) 2_656 2_656 ?
C2 C1 C6 121.6(4) . . ?
C2 C1 N1 120.2(4) . . ?
C6 C1 N1 118.2(4) . . ?
C3 C2 C1 119.3(5) . . ?
C2 C3 C4 120.5(5) . . ?
C5 C4 C3 120.2(5) . . ?
C4 C5 C6 120.9(5) . . ?
C1 C6 C5 117.6(4) . . ?
C1 C6 C7 119.1(4) . . ?
C5 C6 C7 123.3(4) . . ?
C8 C7 C12 117.6(4) . . ?
C8 C7 C6 122.0(4) . . ?
C12 C7 C6 120.4(4) . . ?
C9 C8 C7 121.5(4) . . ?
C8 C9 C10 120.2(4) . . ?
C11 C10 C9 120.2(5) . . ?
C10 C11 C12 120.9(4) . . ?
C11 C12 C7 119.5(4) . . ?
C11 C12 C13 122.9(4) . . ?
C7 C12 C13 117.5(4) . . ?
N2 C13 N1 110.3(4) . . ?
N2 C13 C12 130.0(4) . . ?
N1 C13 C12 119.6(4) . . ?
N1 C14 C15 102.0(3) . . ?
N2 C15 C14 103.9(3) . . ?
N2 C16 C17 112.8(3) . . ?
N3 C17 C18 121.5(4) . . ?
N3 C17 C16 115.4(3) . . ?
C18 C17 C16 123.1(4) . . ?
C17 C18 C19 119.2(4) . . ?
C20 C19 C18 119.2(4) . . ?
C21 C20 C19 118.7(4) . . ?
N3 C21 C20 123.1(4) . . ?
N4 C22 S1 179.2(4) . . ?
N5 C23 S2 179.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        24.20
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.54
_refine_diff_density_min         -0.49
_refine_diff_density_rms         0.08

# Attachment 'compound6.cif'

data_pk355c
_database_code_depnum_ccdc_archive 'CCDC 678284'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H38 Br4 Cu N6 O'
_chemical_formula_weight         1025.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   13.1236(6)
_cell_length_b                   22.2503(11)
_cell_length_c                   13.7765(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.917(2)
_cell_angle_gamma                90.00
_cell_volume                     3936.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2417
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      22.5

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2036
_exptl_absorpt_coefficient_mu    4.658
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4560
_exptl_absorpt_correction_T_max  0.6530
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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 Apex CCD'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            13804
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         23.29
_reflns_number_total             2829
_reflns_number_gt                2157
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex
_computing_cell_refinement       Apex
_computing_data_reduction        Apex
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Wingx

_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)+(0.0649P)²+76.4964P] 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       none
_refine_ls_number_reflns         2829
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Cu Cu 0.0000 0.87570(6) 0.7500 0.0207(4) Uani 1 2 d S . .
Br1 Br 0.0000 0.98756(5) 0.7500 0.0284(4) Uani 1 2 d S . .
Br2 Br -0.13610(6) 0.80298(4) 0.65296(7) 0.0262(3) Uani 1 1 d . . .
Br3 Br 0.42696(15) 0.78222(10) 0.64975(18) 0.0469(6) Uani 0.50 1 d P . .
O1 O 0.1375(13) 0.7670(7) 0.141(3) 0.197(19) Uani 0.50 1 d P . .
N1 N 0.4670(6) 0.8741(3) 0.3814(5) 0.0252(17) Uani 1 1 d . . .
N2 N 0.2988(5) 0.8645(3) 0.3783(5) 0.0238(17) Uani 1 1 d . . .
N3 N 0.0660(5) 0.8786(3) 0.6308(5) 0.0213(16) Uani 1 1 d . . .
C1 C 0.5610(6) 0.9013(4) 0.3778(6) 0.026(2) Uani 1 1 d . . .
C2 C 0.6504(7) 0.8666(4) 0.3793(7) 0.033(2) Uani 1 1 d . . .
H2 H 0.6470 0.8241 0.3844 0.040 Uiso 1 1 calc R . .
C3 C 0.7423(7) 0.8935(5) 0.3736(7) 0.033(2) Uani 1 1 d . . .
H3 H 0.8026 0.8697 0.3751 0.040 Uiso 1 1 calc R . .
C4 C 0.7481(7) 0.9551(5) 0.3656(7) 0.035(2) Uani 1 1 d . . .
H4 H 0.8121 0.9736 0.3610 0.043 Uiso 1 1 calc R . .
C5 C 0.6605(7) 0.9899(5) 0.3644(6) 0.031(2) Uani 1 1 d . . .
H5 H 0.6651 1.0323 0.3593 0.037 Uiso 1 1 calc R . .
C6 C 0.5641(7) 0.9633(4) 0.3706(6) 0.023(2) Uani 1 1 d . . .
C7 C 0.4701(7) 0.9975(4) 0.3729(6) 0.024(2) Uani 1 1 d . . .
C8 C 0.4687(7) 1.0610(4) 0.3678(6) 0.025(2) Uani 1 1 d . . .
H8 H 0.5301 1.0821 0.3621 0.030 Uiso 1 1 calc R . .
C9 C 0.3792(7) 1.0926(4) 0.3710(6) 0.030(2) Uani 1 1 d . . .
H9 H 0.3788 1.1351 0.3642 0.035 Uiso 1 1 calc R . .
C10 C 0.2906(7) 1.0636(4) 0.3839(6) 0.027(2) Uani 1 1 d . . .
H10 H 0.2299 1.0860 0.3879 0.033 Uiso 1 1 calc R . .
C11 C 0.2901(6) 1.0021(4) 0.3909(6) 0.025(2) Uani 1 1 d . . .
H11 H 0.2295 0.9823 0.4024 0.029 Uiso 1 1 calc R . .
C12 C 0.3768(7) 0.9682(4) 0.3815(6) 0.0221(19) Uani 1 1 d . . .
C13 C 0.3768(6) 0.9035(4) 0.3808(6) 0.0205(19) Uani 1 1 d . . .
C14 C 0.4516(7) 0.8086(4) 0.3848(8) 0.035(2) Uani 1 1 d . . .
H14A H 0.4898 0.7915 0.4483 0.043 Uiso 1 1 calc R . .
H14B H 0.4749 0.7883 0.3292 0.043 Uiso 1 1 calc R . .
C15 C 0.3353(7) 0.8026(4) 0.3752(8) 0.033(2) Uani 1 1 d . . .
H15A H 0.3029 0.7830 0.3118 0.040 Uiso 1 1 calc R . .
H15B H 0.3189 0.7788 0.4308 0.040 Uiso 1 1 calc R . .
C16 C 0.1878(7) 0.8753(4) 0.3632(6) 0.025(2) Uani 1 1 d . . .
H16A H 0.1505 0.8423 0.3225 0.030 Uiso 1 1 calc R . .
H16B H 0.1710 0.9132 0.3257 0.030 Uiso 1 1 calc R . .
C17 C 0.1489(6) 0.8795(4) 0.4602(6) 0.023(2) Uani 1 1 d . . .
C18 C 0.2083(6) 0.8640(4) 0.5497(6) 0.026(2) Uani 1 1 d . . .
H18 H 0.2791 0.8530 0.5548 0.031 Uiso 1 1 calc R . .
C19 C 0.1647(7) 0.8644(4) 0.6343(6) 0.024(2) Uani 1 1 d . . .
H19 H 0.2075 0.8541 0.6965 0.029 Uiso 1 1 calc R . .
C20 C 0.0103(7) 0.8969(5) 0.5450(7) 0.038(2) Uani 1 1 d . . .
H20 H -0.0589 0.9103 0.5430 0.045 Uiso 1 1 calc R . .
C21 C 0.0467(7) 0.8975(5) 0.4584(7) 0.039(3) Uani 1 1 d . . .
H21 H 0.0028 0.9101 0.3980 0.047 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
Cu N3 2.010(6) 2_556 ?
Cu N3 2.010(6) . ?
Cu Br1 2.4888(18) . ?
Cu Br2 2.5709(12) . ?
Cu Br2 2.5709(12) 2_556 ?
N1 C13 1.350(10) . ?
N1 C1 1.384(11) . ?
N1 C14 1.474(11) . ?
N2 C13 1.336(11) . ?
N2 C16 1.447(11) . ?
N2 C15 1.463(11) . ?
N3 C20 1.319(11) . ?
N3 C19 1.325(11) . ?
C1 C6 1.383(12) . ?
C1 C2 1.401(12) . ?
C2 C3 1.363(13) . ?
C3 C4 1.378(14) . ?
C4 C5 1.382(13) . ?
C5 C6 1.414(12) . ?
C6 C7 1.456(12) . ?
C7 C12 1.414(12) . ?
C7 C8 1.414(12) . ?
C8 C9 1.377(12) . ?
C9 C10 1.374(13) . ?
C10 C11 1.372(12) . ?
C11 C12 1.393(11) . ?
C12 C13 1.441(12) . ?
C14 C15 1.511(13) . ?
C16 C17 1.529(11) . ?
C17 C18 1.360(12) . ?
C17 C21 1.395(12) . ?
C18 C19 1.400(11) . ?
C20 C21 1.375(13) . ?

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
N3 Cu N3 176.3(4) 2_556 . ?
N3 Cu Br1 88.13(19) 2_556 . ?
N3 Cu Br1 88.13(19) . . ?
N3 Cu Br2 94.3(2) 2_556 . ?
N3 Cu Br2 88.1(2) . . ?
Br1 Cu Br2 129.00(3) . . ?
N3 Cu Br2 88.1(2) 2_556 2_556 ?
N3 Cu Br2 94.3(2) . 2_556 ?
Br1 Cu Br2 129.00(3) . 2_556 ?
Br2 Cu Br2 101.99(6) . 2_556 ?
C13 N1 C1 125.1(7) . . ?
C13 N1 C14 110.7(7) . . ?
C1 N1 C14 124.2(7) . . ?
C13 N2 C16 129.7(7) . . ?
C13 N2 C15 111.0(7) . . ?
C16 N2 C15 118.5(7) . . ?
C20 N3 C19 117.7(7) . . ?
C20 N3 Cu 119.3(6) . . ?
C19 N3 Cu 123.0(6) . . ?
C6 C1 N1 118.6(8) . . ?
C6 C1 C2 120.8(8) . . ?
N1 C1 C2 120.6(8) . . ?
C3 C2 C1 120.4(9) . . ?
C2 C3 C4 120.4(9) . . ?
C3 C4 C5 119.8(9) . . ?
C4 C5 C6 121.1(9) . . ?
C1 C6 C5 117.5(8) . . ?
C1 C6 C7 118.8(8) . . ?
C5 C6 C7 123.7(8) . . ?
C12 C7 C8 117.5(8) . . ?
C12 C7 C6 120.9(8) . . ?
C8 C7 C6 121.6(8) . . ?
C9 C8 C7 120.7(8) . . ?
C10 C9 C8 121.0(8) . . ?
C11 C10 C9 119.6(8) . . ?
C10 C11 C12 121.1(8) . . ?
C11 C12 C7 119.8(8) . . ?
C11 C12 C13 122.9(8) . . ?
C7 C12 C13 117.3(7) . . ?
N2 C13 N1 110.6(7) . . ?
N2 C13 C12 130.4(8) . . ?
N1 C13 C12 119.0(8) . . ?
N1 C14 C15 103.1(7) . . ?
N2 C15 C14 104.2(7) . . ?
N2 C16 C17 113.1(7) . . ?
C18 C17 C21 117.3(8) . . ?
C18 C17 C16 123.0(7) . . ?
C21 C17 C16 119.7(8) . . ?
C17 C18 C19 119.8(8) . . ?
N3 C19 C18 122.3(8) . . ?
N3 C20 C21 123.6(8) . . ?
C20 C21 C17 119.1(9) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        23.29
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.32
_refine_diff_density_min         -0.70
_refine_diff_density_rms         0.14


# Attachment 'Ligand.cif'

data_ys02901
_database_code_depnum_ccdc_archive 'CCDC 682073'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H38 B N3'
_chemical_formula_weight         631.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   10.3685(7)
_cell_length_b                   18.5863(11)
_cell_length_c                   18.5508(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.445(3)
_cell_angle_gamma                90.00
_cell_volume                     3461.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3714
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      19.3

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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 Apex CCD'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            45379
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         22.00
_reflns_number_total             4248
_reflns_number_gt                2842
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex
_computing_cell_refinement       Apex
_computing_data_reduction        Apex
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Wingx

_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)+(0.0657P)²+0.6189P] 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     SHELXL
_refine_ls_extinction_coef       0.0072(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4248
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
N1 N 0.58558(19) 0.06900(11) 0.41819(11) 0.0449(6) Uani 1 1 d . . .
N2 N 0.5157(2) 0.09774(11) 0.29980(12) 0.0502(6) Uani 1 1 d . . .
N3 N 0.2607(3) 0.06832(16) 0.21838(13) 0.0800(8) Uani 1 1 d . . .
B B 0.4494(3) 0.23444(16) -0.02769(17) 0.0518(8) Uani 1 1 d . . .
C1 C 0.6449(2) 0.02885(14) 0.48108(14) 0.0443(7) Uani 1 1 d . . .
C2 C 0.6820(3) 0.06148(16) 0.55067(15) 0.0551(7) Uani 1 1 d . . .
H2 H 0.6662 0.1113 0.5561 0.066 Uiso 1 1 calc R . .
C3 C 0.7418(3) 0.02050(18) 0.61148(16) 0.0633(8) Uani 1 1 d . . .
H3 H 0.7672 0.0422 0.6593 0.076 Uiso 1 1 calc R . .
C4 C 0.7657(3) -0.05232(18) 0.60384(16) 0.0622(8) Uani 1 1 d . . .
H4 H 0.8066 -0.0802 0.6463 0.075 Uiso 1 1 calc R . .
C5 C 0.7301(3) -0.08377(16) 0.53498(16) 0.0582(8) Uani 1 1 d . . .
H5 H 0.7484 -0.1334 0.5302 0.070 Uiso 1 1 calc R . .
C6 C 0.6674(2) -0.04465(14) 0.47151(14) 0.0454(7) Uani 1 1 d . . .
C7 C 0.6243(2) -0.07578(14) 0.39753(14) 0.0473(7) Uani 1 1 d . . .
C8 C 0.6316(3) -0.14997(15) 0.38645(16) 0.0644(8) Uani 1 1 d . . .
H8 H 0.6677 -0.1804 0.4277 0.077 Uiso 1 1 calc R . .
C9 C 0.5875(4) -0.17945(16) 0.31679(19) 0.0794(10) Uani 1 1 d . . .
H9 H 0.5927 -0.2300 0.3105 0.095 Uiso 1 1 calc R . .
C10 C 0.5354(3) -0.13619(17) 0.25553(18) 0.0798(10) Uani 1 1 d . . .
H10 H 0.5059 -0.1570 0.2074 0.096 Uiso 1 1 calc R . .
C11 C 0.5265(3) -0.06347(16) 0.26461(15) 0.0639(8) Uani 1 1 d . . .
H11 H 0.4903 -0.0340 0.2226 0.077 Uiso 1 1 calc R . .
C12 C 0.5702(2) -0.03174(14) 0.33520(15) 0.0465(7) Uani 1 1 d . . .
C13 C 0.5566(2) 0.04423(14) 0.34829(15) 0.0448(7) Uani 1 1 d . . .
C14 C 0.5655(3) 0.14776(13) 0.41986(14) 0.0544(7) Uani 1 1 d . . .
H14A H 0.6513 0.1734 0.4375 0.065 Uiso 1 1 calc R . .
H14B H 0.5058 0.1607 0.4520 0.065 Uiso 1 1 calc R . .
C15 C 0.5017(3) 0.16426(14) 0.33884(15) 0.0635(8) Uani 1 1 d . . .
H15A H 0.4067 0.1771 0.3316 0.076 Uiso 1 1 calc R . .
H15B H 0.5482 0.2044 0.3210 0.076 Uiso 1 1 calc R . .
C16 C 0.4880(3) 0.09795(15) 0.21916(14) 0.0559(8) Uani 1 1 d . . .
H16A H 0.5551 0.0675 0.2041 0.067 Uiso 1 1 calc R . .
H16B H 0.4989 0.1476 0.2024 0.067 Uiso 1 1 calc R . .
C17 C 0.3512(3) 0.07154(14) 0.17943(14) 0.0486(7) Uani 1 1 d . . .
C18 C 0.3250(3) 0.05299(16) 0.10577(16) 0.0636(8) Uani 1 1 d . . .
H18 H 0.3920 0.0578 0.0793 0.076 Uiso 1 1 calc R . .
C19 C 0.2015(3) 0.02746(18) 0.07057(17) 0.0772(10) Uani 1 1 d . . .
H19 H 0.1824 0.0129 0.0199 0.093 Uiso 1 1 calc R . .
C20 C 0.1070(3) 0.0233(2) 0.10959(19) 0.0913(11) Uani 1 1 d . . .
H20 H 0.0200 0.0063 0.0868 0.110 Uiso 1 1 calc R . .
C21 C 0.1402(3) 0.0441(2) 0.18232(19) 0.1061(14) Uani 1 1 d . . .
H21 H 0.0734 0.0413 0.2092 0.127 Uiso 1 1 calc R . .
C22 C 0.4147(3) 0.25272(14) 0.05241(15) 0.0573(8) Uani 1 1 d . . .
C23 C 0.5010(3) 0.29249(16) 0.10803(17) 0.0734(9) Uani 1 1 d . . .
H23 H 0.5854 0.3058 0.1009 0.088 Uiso 1 1 calc R . .
C24 C 0.4691(5) 0.31347(19) 0.17337(19) 0.0940(12) Uani 1 1 d . . .
H24 H 0.5309 0.3409 0.2093 0.113 Uiso 1 1 calc R . .
C25 C 0.3496(6) 0.2950(2) 0.1864(2) 0.1001(14) Uani 1 1 d . . .
H25 H 0.3279 0.3093 0.2311 0.120 Uiso 1 1 calc R . .
C26 C 0.2615(4) 0.25544(19) 0.1341(2) 0.0865(11) Uani 1 1 d . . .
H26 H 0.1781 0.2420 0.1425 0.104 Uiso 1 1 calc R . .
C27 C 0.2939(3) 0.23477(15) 0.06845(17) 0.0677(9) Uani 1 1 d . . .
H27 H 0.2311 0.2073 0.0331 0.081 Uiso 1 1 calc R . .
C28 C 0.3655(3) 0.16324(14) -0.06657(14) 0.0504(7) Uani 1 1 d . . .
C29 C 0.4209(3) 0.09451(15) -0.06424(14) 0.0538(7) Uani 1 1 d . . .
H29 H 0.5128 0.0887 -0.0407 0.065 Uiso 1 1 calc R . .
C30 C 0.3489(3) 0.03458(16) -0.09444(16) 0.0615(8) Uani 1 1 d . . .
H30 H 0.3911 -0.0111 -0.0903 0.074 Uiso 1 1 calc R . .
C31 C 0.2161(3) 0.04065(18) -0.13054(16) 0.0666(9) Uani 1 1 d . . .
H31 H 0.1666 -0.0003 -0.1523 0.080 Uiso 1 1 calc R . .
C32 C 0.1561(3) 0.10739(19) -0.13457(17) 0.0740(9) Uani 1 1 d . . .
H32 H 0.0645 0.1128 -0.1590 0.089 Uiso 1 1 calc R . .
C33 C 0.2303(3) 0.16609(16) -0.10284(16) 0.0676(9) Uani 1 1 d . . .
H33 H 0.1866 0.2113 -0.1058 0.081 Uiso 1 1 calc R . .
C34 C 0.4122(3) 0.30584(14) -0.08239(15) 0.0519(7) Uani 1 1 d . . .
C35 C 0.3701(3) 0.30160(16) -0.15963(16) 0.0670(9) Uani 1 1 d . . .
H35 H 0.3573 0.2553 -0.1819 0.080 Uiso 1 1 calc R . .
C36 C 0.3459(3) 0.3618(2) -0.20604(18) 0.0773(10) Uani 1 1 d . . .
H36 H 0.3166 0.3558 -0.2584 0.093 Uiso 1 1 calc R . .
C37 C 0.3644(3) 0.42942(19) -0.1760(2) 0.0763(10) Uani 1 1 d . . .
H37 H 0.3496 0.4707 -0.2072 0.092 Uiso 1 1 calc R . .
C38 C 0.4045(3) 0.43678(16) -0.1002(2) 0.0683(9) Uani 1 1 d . . .
H38 H 0.4162 0.4834 -0.0786 0.082 Uiso 1 1 calc R . .
C39 C 0.4279(3) 0.37653(15) -0.05504(17) 0.0584(8) Uani 1 1 d . . .
H39 H 0.4562 0.3834 -0.0027 0.070 Uiso 1 1 calc R . .
C40 C 0.6092(3) 0.21590(14) -0.01562(15) 0.0529(7) Uani 1 1 d . . .
C41 C 0.6766(3) 0.22729(14) -0.07157(17) 0.0597(8) Uani 1 1 d . . .
H41 H 0.6311 0.2514 -0.1157 0.072 Uiso 1 1 calc R . .
C42 C 0.8070(3) 0.20483(16) -0.0652(2) 0.0722(9) Uani 1 1 d . . .
H42 H 0.8477 0.2127 -0.1051 0.087 Uiso 1 1 calc R . .
C43 C 0.8767(3) 0.17143(17) -0.0016(2) 0.0788(10) Uani 1 1 d . . .
H43 H 0.9662 0.1568 0.0033 0.095 Uiso 1 1 calc R . .
C44 C 0.8158(3) 0.15937(16) 0.0549(2) 0.0734(9) Uani 1 1 d . . .
H44 H 0.8632 0.1362 0.0993 0.088 Uiso 1 1 calc R . .
C45 C 0.6856(3) 0.18086(15) 0.04739(16) 0.0615(8) Uani 1 1 d . . .
H45 H 0.6457 0.1713 0.0873 0.074 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
N1 C13 1.338(3) . ?
N1 C1 1.392(3) . ?
N1 C14 1.480(3) . ?
N2 C13 1.337(3) . ?
N2 C16 1.451(3) . ?
N2 C15 1.458(3) . ?
N3 C17 1.321(3) . ?
N3 C21 1.340(4) . ?
B C28 1.648(4) . ?
B C22 1.649(4) . ?
B C40 1.652(4) . ?
B C34 1.656(4) . ?
C1 C2 1.391(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.374(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.369(4) . ?
C5 C6 1.398(3) . ?
C6 C7 1.453(3) . ?
C7 C8 1.399(4) . ?
C7 C12 1.413(3) . ?
C8 C9 1.373(4) . ?
C9 C10 1.387(4) . ?
C10 C11 1.368(4) . ?
C11 C12 1.404(3) . ?
C12 C13 1.446(4) . ?
C14 C15 1.515(3) . ?
C16 C17 1.508(4) . ?
C17 C18 1.369(4) . ?
C18 C19 1.368(4) . ?
C19 C20 1.358(4) . ?
C20 C21 1.363(4) . ?
C22 C23 1.397(4) . ?
C22 C27 1.398(4) . ?
C23 C24 1.390(5) . ?
C24 C25 1.364(5) . ?
C25 C26 1.369(5) . ?
C26 C27 1.395(4) . ?
C28 C29 1.397(3) . ?
C28 C33 1.397(4) . ?
C29 C30 1.380(4) . ?
C30 C31 1.378(4) . ?
C31 C32 1.381(4) . ?
C32 C33 1.379(4) . ?
C34 C35 1.392(4) . ?
C34 C39 1.403(4) . ?
C35 C36 1.396(4) . ?
C36 C37 1.369(4) . ?
C37 C38 1.370(4) . ?
C38 C39 1.383(4) . ?
C40 C45 1.399(4) . ?
C40 C41 1.404(4) . ?
C41 C42 1.392(4) . ?
C42 C43 1.370(4) . ?
C43 C44 1.370(4) . ?
C44 C45 1.381(4) . ?

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
C13 N1 C1 125.0(2) . . ?
C13 N1 C14 111.2(2) . . ?
C1 N1 C14 123.2(2) . . ?
C13 N2 C16 130.1(2) . . ?
C13 N2 C15 110.5(2) . . ?
C16 N2 C15 119.4(2) . . ?
C17 N3 C21 116.3(3) . . ?
C28 B C22 110.5(2) . . ?
C28 B C40 107.1(2) . . ?
C22 B C40 111.0(2) . . ?
C28 B C34 111.0(2) . . ?
C22 B C34 108.5(2) . . ?
C40 B C34 108.8(2) . . ?
C2 C1 N1 120.4(2) . . ?
C2 C1 C6 121.7(2) . . ?
N1 C1 C6 117.9(2) . . ?
C3 C2 C1 118.9(3) . . ?
C2 C3 C4 120.8(3) . . ?
C5 C4 C3 119.8(3) . . ?
C4 C5 C6 121.6(3) . . ?
C5 C6 C1 117.1(2) . . ?
C5 C6 C7 123.9(3) . . ?
C1 C6 C7 119.0(2) . . ?
C8 C7 C12 118.4(2) . . ?
C8 C7 C6 121.1(2) . . ?
C12 C7 C6 120.5(2) . . ?
C9 C8 C7 120.9(3) . . ?
C8 C9 C10 120.7(3) . . ?
C11 C10 C9 119.8(3) . . ?
C10 C11 C12 120.9(3) . . ?
C11 C12 C7 119.3(2) . . ?
C11 C12 C13 123.0(2) . . ?
C7 C12 C13 117.6(2) . . ?
N2 C13 N1 110.7(2) . . ?
N2 C13 C12 129.9(2) . . ?
N1 C13 C12 119.4(2) . . ?
N1 C14 C15 102.0(2) . . ?
N2 C15 C14 104.4(2) . . ?
N2 C16 C17 115.0(2) . . ?
N3 C17 C18 122.9(3) . . ?
N3 C17 C16 117.2(2) . . ?
C18 C17 C16 119.9(3) . . ?
C19 C18 C17 119.5(3) . . ?
C20 C19 C18 118.6(3) . . ?
C19 C20 C21 118.3(3) . . ?
N3 C21 C20 124.3(3) . . ?
C23 C22 C27 114.3(3) . . ?
C23 C22 B 122.1(3) . . ?
C27 C22 B 123.4(3) . . ?
C24 C23 C22 123.0(4) . . ?
C25 C24 C23 120.6(4) . . ?
C24 C25 C26 119.0(4) . . ?
C25 C26 C27 120.2(4) . . ?
C26 C27 C22 122.9(3) . . ?
C29 C28 C33 113.9(3) . . ?
C29 C28 B 123.6(2) . . ?
C33 C28 B 122.5(2) . . ?
C30 C29 C28 123.3(3) . . ?
C31 C30 C29 120.4(3) . . ?
C30 C31 C32 118.8(3) . . ?
C33 C32 C31 119.5(3) . . ?
C32 C33 C28 124.2(3) . . ?
C35 C34 C39 113.8(2) . . ?
C35 C34 B 123.4(2) . . ?
C39 C34 B 122.7(2) . . ?
C34 C35 C36 123.5(3) . . ?
C37 C36 C35 120.0(3) . . ?
C36 C37 C38 119.1(3) . . ?
C37 C38 C39 120.2(3) . . ?
C38 C39 C34 123.5(3) . . ?
C45 C40 C41 113.9(3) . . ?
C45 C40 B 123.4(3) . . ?
C41 C40 B 122.4(2) . . ?
C42 C41 C40 123.0(3) . . ?
C43 C42 C41 120.1(3) . . ?
C42 C43 C44 119.3(3) . . ?
C43 C44 C45 120.1(3) . . ?
C44 C45 C40 123.7(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        22.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.13
_refine_diff_density_rms         0.03

