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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_ups1613shi_2_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H38 Cd N8 O10'
_chemical_formula_sum            'C46 H38 Cd N8 O10'
_chemical_formula_weight         975.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   24.6035(5)
_cell_length_b                   11.9649(3)
_cell_length_c                   18.4269(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.5710(10)
_cell_angle_gamma                90.00
_cell_volume                     4933.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    156
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      26.42

_exptl_crystal_description       block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992.0
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41014
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.42
_reflns_number_total             5034
_reflns_number_gt                4082
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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. 

_platon_squeeze_details
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.500  0.000  0.047       510       113 ' '
   2  0.000  0.500  0.244       510       113 ' '
;

_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)+(0.0789P)²+12.5789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5034
_refine_ls_number_parameters     291
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1508
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.0000 0.0000 0.5000 0.04071(15) Uani 1 2 d S . .
C15 C 0.33228(19) -0.2747(4) 0.9089(2) 0.0634(8) Uani 1 1 d . . .
H15 H 0.3037 -0.2577 0.8581 0.076 Uiso 1 1 calc R . .
N1 N 0.05702(12) -0.0480(3) 0.63685(17) 0.0428(7) Uani 1 1 d . . .
C9 C 0.28934(15) -0.0613(3) 1.0204(2) 0.0460(8) Uani 1 1 d . . .
H9 H 0.3219 -0.0654 1.0696 0.055 Uiso 1 1 calc R . .
C7 C 0.19892(17) 0.0219(3) 0.9307(2) 0.0432(8) Uani 1 1 d . . .
H7 H 0.1693 0.0761 0.9178 0.052 Uiso 1 1 calc R . .
C3 C 0.14571(15) -0.0594(3) 0.79396(19) 0.0407(7) Uani 1 1 d . . .
C4 C 0.09441(18) 0.0034(3) 0.7744(2) 0.0512(10) Uani 1 1 d . . .
H4 H 0.0885 0.0436 0.8137 0.061 Uiso 1 1 calc R . .
C5 C 0.05198(18) 0.0066(3) 0.6966(2) 0.0508(10) Uani 1 1 d . . .
H5 H 0.0179 0.0495 0.6852 0.061 Uiso 1 1 calc R . .
C1 C 0.10537(18) -0.1107(4) 0.6559(2) 0.0587(11) Uani 1 1 d . . .
H1 H 0.1093 -0.1519 0.6156 0.070 Uiso 1 1 calc R . .
C2 C 0.15043(17) -0.1186(4) 0.7322(2) 0.0579(11) Uani 1 1 d . . .
H2 H 0.1836 -0.1634 0.7419 0.069 Uiso 1 1 calc R . .
C14 C 0.1230(2) 0.1496(6) 0.5824(3) 0.098(2) Uani 1 1 d . . .
H14 H 0.1232 0.1167 0.6283 0.117 Uiso 1 1 calc R . .
C11 C 0.32951(19) -0.2252(4) 0.9730(2) 0.0634(8) Uani 1 1 d . . .
C6 C 0.19515(15) -0.0598(3) 0.87569(19) 0.0407(7) Uani 1 1 d . . .
N3 N 0.07987(14) 0.1210(3) 0.51276(18) 0.0521(8) Uani 1 1 d . . .
C13 C 0.0842(2) 0.1668(4) 0.4496(2) 0.0620(11) Uani 1 1 d . . .
H13 H 0.0562 0.1460 0.3992 0.074 Uiso 1 1 calc R . .
N2 N 0.23694(12) -0.1393(3) 0.88992(17) 0.0438(7) Uani 1 1 d . . .
C16 C 0.25238(15) 0.1133(3) 1.0639(2) 0.0412(7) Uani 1 1 d . . .
C17 C 0.30600(17) 0.1330(3) 1.1305(2) 0.0511(9) Uani 1 1 d . . .
H17 H 0.3392 0.0888 1.1390 0.061 Uiso 1 1 calc R . .
C10 C 0.28293(15) -0.1391(3) 0.9618(2) 0.0435(8) Uani 1 1 d . . .
C8 C 0.24714(17) 0.0233(3) 1.0058(2) 0.0415(8) Uani 1 1 d . . .
O1 O 0.27039(15) 0.3660(3) 1.22774(18) 0.0679(8) Uani 1 1 d . . .
O2 O 0.36129(17) 0.2422(3) 1.2498(2) 0.0927(13) Uani 1 1 d . . .
C19 C 0.26127(18) 0.2841(3) 1.1719(2) 0.0493(9) Uani 1 1 d . . .
C21 C 0.20452(17) 0.1820(4) 1.0524(2) 0.0590(11) Uani 1 1 d . . .
H21 H 0.1688 0.1713 1.0078 0.071 Uiso 1 1 calc R . .
C20 C 0.20834(19) 0.2664(4) 1.1056(3) 0.0588(10) Uani 1 1 d . . .
H20 H 0.1753 0.3112 1.0968 0.071 Uiso 1 1 calc R . .
C18 C 0.31031(18) 0.2168(3) 1.1835(2) 0.0539(10) Uani 1 1 d . . .
O3 O -0.05817(18) 0.1030(3) 0.5547(3) 0.0963(12) Uani 1 1 d . . .
N4 N -0.05264(16) 0.2058(4) 0.5598(2) 0.0613(9) Uani 1 1 d U . .
C12 C 0.1274(2) 0.2425(4) 0.4537(2) 0.0622(11) Uani 1 1 d . . .
H12 H 0.1275 0.2721 0.4071 0.075 Uiso 1 1 calc R . .
C23 C 0.2210(3) 0.4328(5) 1.2209(4) 0.0885(17) Uani 1 1 d . . .
H23A H 0.2073 0.4749 1.1722 0.133 Uiso 1 1 calc R . .
H23C H 0.2328 0.4831 1.2655 0.133 Uiso 1 1 calc R . .
H23B H 0.1893 0.3856 1.2205 0.133 Uiso 1 1 calc R . .
C22 C 0.4112(3) 0.1750(6) 1.2683(4) 0.115(3) Uani 1 1 d . . .
H22B H 0.4018 0.0999 1.2775 0.172 Uiso 1 1 calc R . .
H22C H 0.4434 0.2029 1.3155 0.172 Uiso 1 1 calc R . .
H22A H 0.4229 0.1758 1.2247 0.172 Uiso 1 1 calc R . .
O5 O -0.0680(2) 0.2614(6) 0.5982(5) 0.194(4) Uani 1 1 d U . .
O4 O -0.0299(3) 0.2370(7) 0.5191(4) 0.174(3) Uani 1 1 d U . .


_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
Cd1 N3 2.373(3) . ?
Cd1 N3 2.373(3) 5_556 ?
Cd1 N1 2.391(3) . ?
Cd1 N1 2.391(3) 5_556 ?
Cd1 O3 2.406(5) . ?
Cd1 O3 2.406(5) 5_556 ?
C15 C11 1.348(6) . ?
C15 C14 1.381(6) 4_546 ?
C15 H15 0.9300 . ?
N1 C1 1.324(5) . ?
N1 C5 1.330(5) . ?
C9 C10 1.384(5) . ?
C9 C8 1.393(5) . ?
C9 H9 0.9300 . ?
C7 C6 1.384(5) . ?
C7 C8 1.399(5) . ?
C7 H7 0.9300 . ?
C3 C4 1.382(5) . ?
C3 C2 1.387(5) . ?
C3 C6 1.491(4) . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C1 C2 1.385(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C14 N3 1.326(5) . ?
C14 C15 1.381(6) 4_556 ?
C14 H14 0.9300 . ?
C11 C12 1.382(5) 4_546 ?
C11 C10 1.491(5) . ?
C6 N2 1.344(4) . ?
N3 C13 1.331(5) . ?
C13 C12 1.374(6) . ?
C13 H13 0.9300 . ?
N2 C10 1.337(4) . ?
C16 C21 1.378(5) . ?
C16 C17 1.399(5) . ?
C16 C8 1.486(5) . ?
C17 C18 1.373(5) . ?
C17 H17 0.9300 . ?
O1 C19 1.370(4) . ?
O1 C23 1.416(6) . ?
O2 C18 1.372(5) . ?
O2 C22 1.386(7) . ?
C19 C20 1.382(6) . ?
C19 C18 1.391(6) . ?
C21 C20 1.384(6) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
O3 N4 1.236(5) . ?
N4 O5 1.145(6) . ?
N4 O4 1.166(6) . ?
C12 C11 1.382(5) 4_556 ?
C12 H12 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23B 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 H22A 0.9600 . ?

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 Cd1 N3 180.0 . 5_556 ?
N3 Cd1 N1 86.77(10) . . ?
N3 Cd1 N1 93.23(10) 5_556 . ?
N3 Cd1 N1 93.24(10) . 5_556 ?
N3 Cd1 N1 86.77(10) 5_556 5_556 ?
N1 Cd1 N1 180.0 . 5_556 ?
N3 Cd1 O3 104.96(13) . . ?
N3 Cd1 O3 75.04(13) 5_556 . ?
N1 Cd1 O3 82.61(12) . . ?
N1 Cd1 O3 97.39(12) 5_556 . ?
N3 Cd1 O3 75.04(13) . 5_556 ?
N3 Cd1 O3 104.96(13) 5_556 5_556 ?
N1 Cd1 O3 97.39(12) . 5_556 ?
N1 Cd1 O3 82.61(12) 5_556 5_556 ?
O3 Cd1 O3 180.00(16) . 5_556 ?
C11 C15 C14 121.0(4) . 4_546 ?
C11 C15 H15 119.5 . . ?
C14 C15 H15 119.5 4_546 . ?
C1 N1 C5 116.2(3) . . ?
C1 N1 Cd1 119.0(2) . . ?
C5 N1 Cd1 122.6(2) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C4 C3 C2 116.3(3) . . ?
C4 C3 C6 122.6(3) . . ?
C2 C3 C6 121.0(3) . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 123.8(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
N1 C1 C2 124.0(4) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N3 C14 C15 124.0(4) . 4_556 ?
N3 C14 H14 118.0 . . ?
C15 C14 H14 118.0 4_556 . ?
C15 C11 C12 115.9(4) . 4_546 ?
C15 C11 C10 119.9(3) . . ?
C12 C11 C10 124.2(4) 4_546 . ?
N2 C6 C7 123.0(3) . . ?
N2 C6 C3 115.9(3) . . ?
C7 C6 C3 121.0(3) . . ?
C14 N3 C13 114.7(4) . . ?
C14 N3 Cd1 123.4(3) . . ?
C13 N3 Cd1 121.9(2) . . ?
N3 C13 C12 124.3(3) . . ?
N3 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
C10 N2 C6 117.1(3) . . ?
C21 C16 C17 117.9(3) . . ?
C21 C16 C8 120.6(3) . . ?
C17 C16 C8 121.5(3) . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
N2 C10 C9 123.3(3) . . ?
N2 C10 C11 114.9(3) . . ?
C9 C10 C11 121.7(3) . . ?
C9 C8 C7 116.1(3) . . ?
C9 C8 C16 123.6(3) . . ?
C7 C8 C16 120.3(3) . . ?
C19 O1 C23 118.1(4) . . ?
C18 O2 C22 118.6(4) . . ?
O1 C19 C20 125.0(4) . . ?
O1 C19 C18 115.9(3) . . ?
C20 C19 C18 119.1(3) . . ?
C16 C21 C20 121.6(4) . . ?
C16 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
O2 C18 C17 124.5(4) . . ?
O2 C18 C19 115.0(4) . . ?
C17 C18 C19 120.5(3) . . ?
N4 O3 Cd1 118.4(4) . . ?
O5 N4 O4 125.5(7) . . ?
O5 N4 O3 124.8(6) . . ?
O4 N4 O3 109.7(6) . . ?
C13 C12 C11 120.0(4) . 4_556 ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 4_556 . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cd1 N1 C1 107.9(3) 5_556 . . . ?
O3 Cd1 N1 C1 -177.6(3) . . . . ?
O3 Cd1 N1 C1 2.4(3) 5_556 . . . ?
N3 Cd1 N1 C5 90.5(3) . . . . ?
N3 Cd1 N1 C5 -89.5(3) 5_556 . . . ?
O3 Cd1 N1 C5 -15.1(3) . . . . ?
O3 Cd1 N1 C5 164.9(3) 5_556 . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C6 C3 C4 C5 175.6(4) . . . . ?
C1 N1 C5 C4 2.0(6) . . . . ?
Cd1 N1 C5 C4 -161.0(3) . . . . ?
C3 C4 C5 N1 -0.1(7) . . . . ?
C5 N1 C1 C2 -2.3(7) . . . . ?
Cd1 N1 C1 C2 161.4(4) . . . . ?
N1 C1 C2 C3 0.8(7) . . . . ?
C4 C3 C2 C1 1.1(6) . . . . ?
C6 C3 C2 C1 -175.9(4) . . . . ?
C14 C15 C11 C12 -1.8(8) 4_546 . . 4_546 ?
C14 C15 C11 C10 176.5(5) 4_546 . . . ?
C8 C7 C6 N2 -1.3(6) . . . . ?
C8 C7 C6 C3 -176.9(3) . . . . ?
C4 C3 C6 N2 168.3(4) . . . . ?
C2 C3 C6 N2 -14.9(5) . . . . ?
C4 C3 C6 C7 -15.8(6) . . . . ?
C2 C3 C6 C7 161.0(4) . . . . ?
C15 C14 N3 C13 3.4(9) 4_556 . . . ?
C15 C14 N3 Cd1 -175.9(5) 4_556 . . . ?
N1 Cd1 N3 C14 -13.6(5) . . . . ?
N1 Cd1 N3 C14 166.4(5) 5_556 . . . ?
O3 Cd1 N3 C14 67.9(5) . . . . ?
O3 Cd1 N3 C14 -112.1(5) 5_556 . . . ?
N1 Cd1 N3 C13 167.2(4) . . . . ?
N1 Cd1 N3 C13 -12.8(4) 5_556 . . . ?
O3 Cd1 N3 C13 -111.3(4) . . . . ?
O3 Cd1 N3 C13 68.7(4) 5_556 . . . ?
C14 N3 C13 C12 -3.4(8) . . . . ?
Cd1 N3 C13 C12 175.9(4) . . . . ?
C7 C6 N2 C10 1.8(5) . . . . ?
C3 C6 N2 C10 177.6(3) . . . . ?
C21 C16 C17 C18 1.3(6) . . . . ?
C8 C16 C17 C18 179.8(4) . . . . ?
C6 N2 C10 C9 -0.7(5) . . . . ?
C6 N2 C10 C11 -177.0(4) . . . . ?
C8 C9 C10 N2 -0.8(6) . . . . ?
C8 C9 C10 C11 175.2(4) . . . . ?
C15 C11 C10 N2 17.9(6) . . . . ?
C12 C11 C10 N2 -164.0(5) 4_546 . . . ?
C15 C11 C10 C9 -158.5(5) . . . . ?
C12 C11 C10 C9 19.7(7) 4_546 . . . ?
C10 C9 C8 C7 1.3(6) . . . . ?
C10 C9 C8 C16 -176.7(4) . . . . ?
C6 C7 C8 C9 -0.3(6) . . . . ?
C6 C7 C8 C16 177.8(3) . . . . ?
C21 C16 C8 C9 -168.0(4) . . . . ?
C17 C16 C8 C9 13.5(6) . . . . ?
C21 C16 C8 C7 14.0(6) . . . . ?
C17 C16 C8 C7 -164.4(4) . . . . ?
C23 O1 C19 C20 4.9(6) . . . . ?
C23 O1 C19 C18 -176.6(4) . . . . ?
C17 C16 C21 C20 -1.5(6) . . . . ?
C8 C16 C21 C20 -180.0(4) . . . . ?
O1 C19 C20 C21 179.0(4) . . . . ?
C18 C19 C20 C21 0.5(6) . . . . ?
C16 C21 C20 C19 0.6(7) . . . . ?
C22 O2 C18 C17 -4.4(8) . . . . ?
C22 O2 C18 C19 176.3(6) . . . . ?
C16 C17 C18 O2 -179.4(4) . . . . ?
C16 C17 C18 C19 -0.2(6) . . . . ?
O1 C19 C18 O2 0.0(6) . . . . ?
C20 C19 C18 O2 178.5(4) . . . . ?
O1 C19 C18 C17 -179.3(4) . . . . ?
C20 C19 C18 C17 -0.7(6) . . . . ?
N3 Cd1 O3 N4 20.2(4) . . . . ?
N3 Cd1 O3 N4 -159.8(4) 5_556 . . . ?
N1 Cd1 O3 N4 104.8(3) . . . . ?
N1 Cd1 O3 N4 -75.2(3) 5_556 . . . ?
Cd1 O3 N4 O5 -163.7(5) . . . . ?
Cd1 O3 N4 O4 16.8(6) . . . . ?
N3 C13 C12 C11 0.9(8) . . . 4_556 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.151
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.080
_database_code_depnum_ccdc_archive 'CCDC 978705'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ups1986shibr_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H38 Br2 Cd N6 O4'
_chemical_formula_sum            'C46 H38 Br2 Cd N6 O4'
_chemical_formula_weight         1011.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   24.665(2)
_cell_length_b                   11.9542(11)
_cell_length_c                   17.8777(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.764(4)
_cell_angle_gamma                90.00
_cell_volume                     4860.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    114
_cell_measurement_theta_min      1.79
_cell_measurement_theta_max      28.32

_exptl_crystal_description       Block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2024.0
_exptl_absorpt_coefficient_mu    2.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_T_max  0.757
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16597
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         28.32
_reflns_number_total             5943
_reflns_number_gt                4497
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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.

_platon_squeeze_details 
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.000  0.000 -0.001       578        78 ' '
   2  0.500  0.500  0.244       578        78 ' '

;

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5943
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.0000 0.5000 0.0000 0.02052(11) Uani 1 2 d S . .
Br1 Br -0.046642(15) 0.33036(4) 0.05594(2) 0.03378(13) Uani 1 1 d . . .
N1 N 0.05727(12) 0.5569(3) 0.14186(16) 0.0238(6) Uani 1 1 d . . .
N2 N 0.23755(12) 0.6438(2) 0.39450(16) 0.0213(6) Uani 1 1 d . . .
C16 C 0.25521(14) 0.3822(3) 0.56778(18) 0.0214(7) Uani 1 1 d . . .
C8 C 0.24855(15) 0.4755(3) 0.51000(19) 0.0199(7) Uani 1 1 d . . .
C19 C 0.26791(16) 0.2059(3) 0.67694(19) 0.0255(7) Uani 1 1 d . . .
C10 C 0.28421(14) 0.6394(3) 0.46473(19) 0.0200(6) Uani 1 1 d . . .
C9 C 0.29096(14) 0.5579(3) 0.52408(19) 0.0220(7) Uani 1 1 d . . .
H9 H 0.3237 0.5591 0.5727 0.026 Uiso 1 1 calc R . .
C20 C 0.31709(15) 0.2691(3) 0.68219(19) 0.0238(7) Uani 1 1 d . . .
C17 C 0.20718(15) 0.3178(3) 0.5635(2) 0.0234(7) Uani 1 1 d . . .
H17 H 0.1703 0.3340 0.5242 0.028 Uiso 1 1 calc R . .
C7 C 0.19980(15) 0.4804(3) 0.43645(19) 0.0211(7) Uani 1 1 d . . .
H7 H 0.1702 0.4270 0.4247 0.025 Uiso 1 1 calc R . .
C21 C 0.31090(15) 0.3570(3) 0.62834(19) 0.0226(7) Uani 1 1 d . . .
H21 H 0.3435 0.3993 0.6322 0.027 Uiso 1 1 calc R . .
C11 C 0.33066(13) 0.7252(3) 0.47596(19) 0.0201(6) Uani 1 1 d . . .
C1 C 0.10593(15) 0.6196(3) 0.1594(2) 0.0261(8) Uani 1 1 d . . .
H1 H 0.1099 0.6606 0.1176 0.031 Uiso 1 1 calc R . .
C18 C 0.21334(15) 0.2292(3) 0.61700(19) 0.0253(7) Uani 1 1 d . . .
H18 H 0.1809 0.1858 0.6124 0.030 Uiso 1 1 calc R . .
C2 C 0.15026(14) 0.6269(3) 0.2355(2) 0.0244(7) Uani 1 1 d . . .
H2 H 0.1831 0.6711 0.2438 0.029 Uiso 1 1 calc R . .
C6 C 0.19548(14) 0.5645(3) 0.38108(19) 0.0206(7) Uani 1 1 d . . .
C3 C 0.14550(14) 0.5675(3) 0.30006(19) 0.0223(7) Uani 1 1 d . . .
C5 C 0.05193(15) 0.5033(3) 0.2050(2) 0.0273(8) Uani 1 1 d . . .
H5 H 0.0181 0.4616 0.1954 0.033 Uiso 1 1 calc R . .
C23 C 0.22999(18) 0.0576(4) 0.7335(3) 0.0406(10) Uani 1 1 d . . .
H23A H 0.2009 0.1076 0.7381 0.061 Uiso 1 1 calc R . .
H23B H 0.2429 0.0073 0.7789 0.061 Uiso 1 1 calc R . .
H23C H 0.2132 0.0155 0.6841 0.061 Uiso 1 1 calc R . .
C4 C 0.09406(16) 0.5072(3) 0.2833(2) 0.0275(8) Uani 1 1 d . . .
H4 H 0.0879 0.4692 0.3248 0.033 Uiso 1 1 calc R . .
C22 C 0.42152(17) 0.2905(5) 0.7423(3) 0.0482(12) Uani 1 1 d . . .
H22A H 0.4237 0.2802 0.6903 0.072 Uiso 1 1 calc R . .
H22B H 0.4552 0.2570 0.7836 0.072 Uiso 1 1 calc R . .
H22C H 0.4207 0.3691 0.7531 0.072 Uiso 1 1 calc R . .
N3 N 0.07968(12) 0.3795(3) 0.01018(17) 0.0247(6) Uani 1 1 d . . .
C13 C 0.08394(17) 0.3309(3) -0.0545(2) 0.0307(8) Uani 1 1 d . . .
H13 H 0.0566 0.3503 -0.1055 0.037 Uiso 1 1 calc R . .
C14 C 0.12132(17) 0.3515(4) 0.0823(2) 0.0429(11) Uani 1 1 d . . .
H14 H 0.1197 0.3840 0.1287 0.051 Uiso 1 1 calc R . .
C12 C 0.12588(17) 0.2549(3) -0.0503(2) 0.0315(8) Uani 1 1 d . . .
H12 H 0.1256 0.2222 -0.0976 0.038 Uiso 1 1 calc R . .
C15 C 0.33352(17) 0.7771(4) 0.4083(2) 0.0412(11) Uani 1 1 d . . .
H15 H 0.3053 0.7622 0.3570 0.049 Uiso 1 1 calc R . .
O1 O 0.36925(11) 0.2389(2) 0.74231(14) 0.0345(7) Uani 1 1 d . . .
O2 O 0.27871(11) 0.1205(2) 0.73276(15) 0.0321(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N3 2.386(3) 5_565 ?
Cd1 N3 2.386(3) . ?
Cd1 N1 2.473(3) 5_565 ?
Cd1 N1 2.473(3) . ?
Cd1 Br1 2.7067(4) 5_565 ?
Cd1 Br1 2.7067(4) . ?
N1 C1 1.345(4) . ?
N1 C5 1.347(4) . ?
N2 C10 1.336(4) . ?
N2 C6 1.357(4) . ?
C16 C17 1.390(5) . ?
C16 C21 1.414(4) . ?
C16 C8 1.485(5) . ?
C8 C9 1.387(5) . ?
C8 C7 1.398(4) . ?
C19 O2 1.380(4) . ?
C19 C18 1.386(5) . ?
C19 C20 1.401(5) . ?
C10 C9 1.402(5) . ?
C10 C11 1.492(5) . ?
C9 H9 0.9300 . ?
C20 O1 1.368(4) . ?
C20 C21 1.393(5) . ?
C17 C18 1.396(5) . ?
C17 H17 0.9300 . ?
C7 C6 1.386(4) . ?
C7 H7 0.9300 . ?
C21 H21 0.9300 . ?
C11 C15 1.386(5) . ?
C11 C12 1.392(4) 4 ?
C1 C2 1.379(4) . ?
C1 H1 0.9300 . ?
C18 H18 0.9300 . ?
C2 C3 1.398(4) . ?
C2 H2 0.9300 . ?
C6 C3 1.496(4) . ?
C3 C4 1.388(5) . ?
C5 C4 1.385(5) . ?
C5 H5 0.9300 . ?
C23 O2 1.422(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C4 H4 0.9300 . ?
C22 O1 1.429(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N3 C13 1.335(5) . ?
N3 C14 1.344(4) . ?
C13 C12 1.357(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(5) 4_545 ?
C14 H14 0.9300 . ?
C12 C11 1.392(4) 4_545 ?
C12 H12 0.9300 . ?
C15 C14 1.383(5) 4 ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cd1 N3 180.0 5_565 . ?
N3 Cd1 N1 87.76(10) 5_565 5_565 ?
N3 Cd1 N1 92.25(10) . 5_565 ?
N3 Cd1 N1 92.24(10) 5_565 . ?
N3 Cd1 N1 87.75(10) . . ?
N1 Cd1 N1 180.0 5_565 . ?
N3 Cd1 Br1 88.56(7) 5_565 5_565 ?
N3 Cd1 Br1 91.44(7) . 5_565 ?
N1 Cd1 Br1 89.01(7) 5_565 5_565 ?
N1 Cd1 Br1 90.99(7) . 5_565 ?
N3 Cd1 Br1 91.44(7) 5_565 . ?
N3 Cd1 Br1 88.57(7) . . ?
N1 Cd1 Br1 90.99(7) 5_565 . ?
N1 Cd1 Br1 89.01(7) . . ?
Br1 Cd1 Br1 180.0 5_565 . ?
C1 N1 C5 115.9(3) . . ?
C1 N1 Cd1 119.8(2) . . ?
C5 N1 Cd1 121.7(2) . . ?
C10 N2 C6 117.4(3) . . ?
C17 C16 C21 118.6(3) . . ?
C17 C16 C8 121.0(3) . . ?
C21 C16 C8 120.4(3) . . ?
C9 C8 C7 117.0(3) . . ?
C9 C8 C16 122.3(3) . . ?
C7 C8 C16 120.6(3) . . ?
O2 C19 C18 124.4(3) . . ?
O2 C19 C20 115.5(3) . . ?
C18 C19 C20 120.0(3) . . ?
N2 C10 C9 123.1(3) . . ?
N2 C10 C11 115.9(3) . . ?
C9 C10 C11 121.0(3) . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
O1 C20 C21 124.1(3) . . ?
O1 C20 C19 115.9(3) . . ?
C21 C20 C19 120.0(3) . . ?
C16 C17 C18 121.2(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C20 C21 C16 120.3(3) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C15 C11 C12 116.0(3) . 4 ?
C15 C11 C10 119.1(3) . . ?
C12 C11 C10 124.9(3) 4 . ?
N1 C1 C2 124.1(3) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N2 C6 C7 122.6(3) . . ?
N2 C6 C3 116.2(3) . . ?
C7 C6 C3 121.1(3) . . ?
C4 C3 C2 116.6(3) . . ?
C4 C3 C6 122.6(3) . . ?
C2 C3 C6 120.7(3) . . ?
N1 C5 C4 123.6(3) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 N3 C14 115.8(3) . . ?
C13 N3 Cd1 122.4(2) . . ?
C14 N3 Cd1 121.7(3) . . ?
N3 C13 C12 123.8(3) . . ?
N3 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?
N3 C14 C15 123.9(4) . 4_545 ?
N3 C14 H14 118.1 . . ?
C15 C14 H14 118.1 4_545 . ?
C13 C12 C11 120.9(3) . 4_545 ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 4_545 . ?
C14 C15 C11 119.5(3) 4 . ?
C14 C15 H15 120.2 4 . ?
C11 C15 H15 120.2 . . ?
C20 O1 C22 117.4(3) . . ?
C19 O2 C23 118.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cd1 N1 C1 -110.0(3) 5_565 . . . ?
N3 Cd1 N1 C1 70.0(3) . . . . ?
Br1 Cd1 N1 C1 -21.4(3) 5_565 . . . ?
Br1 Cd1 N1 C1 158.6(3) . . . . ?
N3 Cd1 N1 C5 89.0(3) 5_565 . . . ?
N3 Cd1 N1 C5 -91.0(3) . . . . ?
Br1 Cd1 N1 C5 177.6(3) 5_565 . . . ?
Br1 Cd1 N1 C5 -2.4(3) . . . . ?
C17 C16 C8 C9 163.6(3) . . . . ?
C21 C16 C8 C9 -16.6(5) . . . . ?
C17 C16 C8 C7 -19.5(5) . . . . ?
C21 C16 C8 C7 160.2(3) . . . . ?
C6 N2 C10 C9 -0.4(5) . . . . ?
C6 N2 C10 C11 177.7(3) . . . . ?
C7 C8 C9 C10 -1.5(5) . . . . ?
C16 C8 C9 C10 175.5(3) . . . . ?
N2 C10 C9 C8 1.6(5) . . . . ?
C11 C10 C9 C8 -176.4(3) . . . . ?
O2 C19 C20 O1 -0.7(5) . . . . ?
C18 C19 C20 O1 -178.9(3) . . . . ?
O2 C19 C20 C21 179.7(3) . . . . ?
C18 C19 C20 C21 1.5(5) . . . . ?
C21 C16 C17 C18 -0.6(5) . . . . ?
C8 C16 C17 C18 179.2(3) . . . . ?
C9 C8 C7 C6 0.4(5) . . . . ?
C16 C8 C7 C6 -176.6(3) . . . . ?
O1 C20 C21 C16 179.8(3) . . . . ?
C19 C20 C21 C16 -0.6(5) . . . . ?
C17 C16 C21 C20 0.1(5) . . . . ?
C8 C16 C21 C20 -179.7(3) . . . . ?
N2 C10 C11 C15 -21.0(5) . . . . ?
C9 C10 C11 C15 157.2(4) . . . . ?
N2 C10 C11 C12 162.0(3) . . . 4 ?
C9 C10 C11 C12 -19.8(5) . . . 4 ?
C5 N1 C1 C2 3.2(6) . . . . ?
Cd1 N1 C1 C2 -158.9(3) . . . . ?
O2 C19 C18 C17 -180.0(3) . . . . ?
C20 C19 C18 C17 -1.9(5) . . . . ?
C16 C17 C18 C19 1.5(5) . . . . ?
N1 C1 C2 C3 -0.8(6) . . . . ?
C10 N2 C6 C7 -0.7(5) . . . . ?
C10 N2 C6 C3 -176.6(3) . . . . ?
C8 C7 C6 N2 0.8(5) . . . . ?
C8 C7 C6 C3 176.4(3) . . . . ?
C1 C2 C3 C4 -2.5(5) . . . . ?
C1 C2 C3 C6 173.7(3) . . . . ?
N2 C6 C3 C4 -167.0(3) . . . . ?
C7 C6 C3 C4 17.1(5) . . . . ?
N2 C6 C3 C2 17.1(5) . . . . ?
C7 C6 C3 C2 -158.8(3) . . . . ?
C1 N1 C5 C4 -2.4(6) . . . . ?
Cd1 N1 C5 C4 159.3(3) . . . . ?
N1 C5 C4 C3 -0.7(6) . . . . ?
C2 C3 C4 C5 3.2(6) . . . . ?
C6 C3 C4 C5 -172.9(3) . . . . ?
N1 Cd1 N3 C13 12.4(3) 5_565 . . . ?
N1 Cd1 N3 C13 -167.6(3) . . . . ?
Br1 Cd1 N3 C13 -76.7(3) 5_565 . . . ?
Br1 Cd1 N3 C13 103.3(3) . . . . ?
N1 Cd1 N3 C14 -163.7(3) 5_565 . . . ?
N1 Cd1 N3 C14 16.3(3) . . . . ?
Br1 Cd1 N3 C14 107.2(3) 5_565 . . . ?
Br1 Cd1 N3 C14 -72.8(3) . . . . ?
C14 N3 C13 C12 2.0(6) . . . . ?
Cd1 N3 C13 C12 -174.3(3) . . . . ?
C13 N3 C14 C15 -0.1(7) . . . 4_545 ?
Cd1 N3 C14 C15 176.2(4) . . . 4_545 ?
N3 C13 C12 C11 -2.2(6) . . . 4_545 ?
C12 C11 C15 C14 1.4(6) 4 . . 4 ?
C10 C11 C15 C14 -175.9(4) . . . 4 ?
C21 C20 O1 C22 -9.1(5) . . . . ?
C19 C20 O1 C22 171.3(4) . . . . ?
C18 C19 O2 C23 -5.5(5) . . . . ?
C20 C19 O2 C23 176.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         1.064
_refine_diff_density_min         -1.613
_refine_diff_density_rms         0.116
_database_code_depnum_ccdc_archive 'CCDC 978706'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ups1722shi_1_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H38 Cd I2 N6 O4'
_chemical_formula_sum            'C46 H38 Cd I2 N6 O4'
_chemical_formula_weight         1105.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   25.6110(7)
_cell_length_b                   11.5667(3)
_cell_length_c                   18.5397(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.3450(10)
_cell_angle_gamma                90.00
_cell_volume                     5003.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    189
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      26.40

_exptl_crystal_description       Block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2168.0
_exptl_absorpt_coefficient_mu    1.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31991
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.40
_reflns_number_total             5122
_reflns_number_gt                4215
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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. 

_platon_squeeze_details 
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.000  0.000 -0.008       570        74 ' '
   2  0.500  0.500  0.748       570        74 ' '

;

_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)+(0.0953P)²+20.2693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5122
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   0.809
_refine_ls_restrained_S_all      0.809
_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
I1 I 1.043423(11) 0.69206(3) 0.442305(16) 0.04845(12) Uani 1 1 d . . .
Cd1 Cd 1.0000 0.5000 0.5000 0.03227(12) Uani 1 2 d S . .
N1 N 0.94128(13) 0.4392(3) 0.35629(18) 0.0363(7) Uani 1 1 d . . .
C8 C 0.75375(16) 0.5221(3) -0.0054(2) 0.0324(8) Uani 1 1 d . . .
C11 C 0.74765(16) 0.6137(3) -0.0642(2) 0.0346(8) Uani 1 1 d . . .
C6 C 0.80388(14) 0.4335(3) 0.1225(2) 0.0302(7) Uani 1 1 d . . .
C7 C 0.80054(15) 0.5179(3) 0.0677(2) 0.0334(8) Uani 1 1 d . . .
H7 H 0.8298 0.5720 0.0798 0.040 Uiso 1 1 calc R . .
C10 C 0.71764(15) 0.3570(3) 0.0395(2) 0.0332(8) Uani 1 1 d . . .
C9 C 0.71179(15) 0.4363(3) -0.0193(2) 0.0351(8) Uani 1 1 d . . .
H9 H 0.6802 0.4328 -0.0679 0.042 Uiso 1 1 calc R . .
C12 C 0.79446(19) 0.6791(4) -0.0587(3) 0.0462(10) Uani 1 1 d . . .
H12 H 0.8302 0.6639 -0.0182 0.055 Uiso 1 1 calc R . .
C3 C 0.85315(15) 0.4304(3) 0.2022(2) 0.0323(7) Uani 1 1 d . . .
C16 C 0.69474(18) 0.6381(3) -0.1256(2) 0.0401(9) Uani 1 1 d . . .
H16 H 0.6627 0.5954 -0.1306 0.048 Uiso 1 1 calc R . .
C1 C 0.89258(18) 0.3801(4) 0.3397(2) 0.0484(10) Uani 1 1 d . . .
H1 H 0.8883 0.3413 0.3808 0.058 Uiso 1 1 calc R . .
C2 C 0.84862(18) 0.3735(4) 0.2652(2) 0.0446(10) Uani 1 1 d . . .
H2 H 0.8159 0.3309 0.2571 0.053 Uiso 1 1 calc R . .
C5 C 0.94582(17) 0.4901(4) 0.2947(2) 0.0411(9) Uani 1 1 d . . .
H5 H 0.9795 0.5300 0.3038 0.049 Uiso 1 1 calc R . .
C13 C 0.78905(19) 0.7666(4) -0.1123(3) 0.0466(10) Uani 1 1 d . . .
H13 H 0.8210 0.8098 -0.1072 0.056 Uiso 1 1 calc R . .
C4 C 0.90406(16) 0.4876(4) 0.2186(2) 0.0399(9) Uani 1 1 d . . .
H4 H 0.9101 0.5246 0.1782 0.048 Uiso 1 1 calc R . .
C15 C 0.6895(2) 0.7252(4) -0.1793(2) 0.0463(10) Uani 1 1 d . . .
C14 C 0.7368(2) 0.7900(3) -0.1730(3) 0.0427(10) Uani 1 1 d . . .
N2 N 0.76270(13) 0.3545(3) 0.10989(17) 0.0330(6) Uani 1 1 d . . .
O2 O 0.72694(17) 0.8742(3) -0.22898(19) 0.0613(9) Uani 1 1 d . . .
O1 O 0.63891(16) 0.7550(3) -0.2403(2) 0.0721(11) Uani 1 1 d . . .
C18 C 0.67082(15) 0.2708(3) 0.0285(2) 0.0338(8) Uani 1 1 d . . .
C19 C 0.62986(18) 0.2388(4) -0.0446(2) 0.0434(9) Uani 1 1 d . . .
H19 H 0.6313 0.2678 -0.0906 0.052 Uiso 1 1 calc R . .
C17 C 0.6663(2) 0.2242(5) 0.0940(3) 0.0621(14) Uani 1 1 d . . .
H17 H 0.6930 0.2425 0.1446 0.075 Uiso 1 1 calc R . .
C22 C 0.7741(3) 0.9398(5) -0.2276(4) 0.0786(18) Uani 1 1 d . . .
H22A H 0.7925 0.9775 -0.1772 0.118 Uiso 1 1 calc R . .
H22B H 0.7607 0.9970 -0.2688 0.118 Uiso 1 1 calc R . .
H22C H 0.8009 0.8896 -0.2359 0.118 Uiso 1 1 calc R . .
N3 N 0.91819(13) 0.6181(3) 0.48642(19) 0.0372(7) Uani 1 1 d . . .
C20 C 0.91315(18) 0.6639(4) 0.5492(3) 0.0457(10) Uani 1 1 d . . .
H20 H 0.9404 0.6440 0.5992 0.055 Uiso 1 1 calc R . .
C21 C 0.8788(2) 0.6497(5) 0.4164(3) 0.0633(15) Uani 1 1 d . . .
H21 H 0.8815 0.6201 0.3714 0.076 Uiso 1 1 calc R . .
C23 C 0.5888(3) 0.6941(6) -0.2467(4) 0.106(3) Uani 1 1 d . . .
H23A H 0.5922 0.6143 -0.2582 0.159 Uiso 1 1 calc R . .
H23B H 0.5558 0.7271 -0.2886 0.159 Uiso 1 1 calc R . .
H23C H 0.5846 0.7000 -0.1977 0.159 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
I1 Cd1 2.8804(3) . ?
Cd1 N3 2.426(3) 5_766 ?
Cd1 N3 2.426(3) . ?
Cd1 N1 2.560(3) 5_766 ?
Cd1 N1 2.560(3) . ?
Cd1 I1 2.8804(3) 5_766 ?
N1 C5 1.332(5) . ?
N1 C1 1.342(5) . ?
C8 C7 1.391(5) . ?
C8 C9 1.407(5) . ?
C8 C11 1.481(5) . ?
C11 C12 1.385(6) . ?
C11 C16 1.393(5) . ?
C6 N2 1.341(5) . ?
C6 C7 1.386(5) . ?
C6 C3 1.497(5) . ?
C7 H7 0.9300 . ?
C10 N2 1.339(5) . ?
C10 C9 1.386(5) . ?
C10 C18 1.508(5) . ?
C9 H9 0.9300 . ?
C12 C13 1.386(6) . ?
C12 H12 0.9300 . ?
C3 C4 1.380(5) . ?
C3 C2 1.386(5) . ?
C16 C15 1.383(6) . ?
C16 H16 0.9300 . ?
C1 C2 1.378(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C5 C4 1.375(5) . ?
C5 H5 0.9300 . ?
C13 C14 1.374(6) . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C15 O1 1.366(5) . ?
C15 C14 1.389(7) . ?
C14 O2 1.369(5) . ?
O2 C22 1.417(7) . ?
O1 C23 1.426(8) . ?
C18 C17 1.376(6) . ?
C18 C19 1.379(5) . ?
C19 C20 1.376(6) 4_645 ?
C19 H19 0.9300 . ?
C17 C21 1.388(6) 4_645 ?
C17 H17 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N3 C21 1.325(5) . ?
N3 C20 1.333(5) . ?
C20 C19 1.376(6) 4_655 ?
C20 H20 0.9300 . ?
C21 C17 1.388(6) 4_655 ?
C21 H21 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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 Cd1 N3 180.00(16) 5_766 . ?
N3 Cd1 N1 86.27(11) 5_766 5_766 ?
N3 Cd1 N1 93.73(11) . 5_766 ?
N3 Cd1 N1 93.73(11) 5_766 . ?
N3 Cd1 N1 86.27(11) . . ?
N1 Cd1 N1 180.000(1) 5_766 . ?
N3 Cd1 I1 91.36(8) 5_766 . ?
N3 Cd1 I1 88.64(8) . . ?
N1 Cd1 I1 91.34(7) 5_766 . ?
N1 Cd1 I1 88.66(7) . . ?
N3 Cd1 I1 88.64(8) 5_766 5_766 ?
N3 Cd1 I1 91.36(8) . 5_766 ?
N1 Cd1 I1 88.66(7) 5_766 5_766 ?
N1 Cd1 I1 91.34(7) . 5_766 ?
I1 Cd1 I1 180.0 . 5_766 ?
C5 N1 C1 115.5(3) . . ?
C5 N1 Cd1 123.3(3) . . ?
C1 N1 Cd1 118.1(3) . . ?
C7 C8 C9 116.1(3) . . ?
C7 C8 C11 121.9(3) . . ?
C9 C8 C11 122.0(3) . . ?
C12 C11 C16 118.1(4) . . ?
C12 C11 C8 120.7(4) . . ?
C16 C11 C8 121.2(3) . . ?
N2 C6 C7 123.0(3) . . ?
N2 C6 C3 116.0(3) . . ?
C7 C6 C3 120.9(3) . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
N2 C10 C9 123.5(3) . . ?
N2 C10 C18 115.8(3) . . ?
C9 C10 C18 120.6(3) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C12 C13 121.2(4) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C4 C3 C2 116.2(3) . . ?
C4 C3 C6 122.8(3) . . ?
C2 C3 C6 120.9(3) . . ?
C15 C16 C11 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N1 C1 C2 123.8(4) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N1 C5 C4 124.4(4) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O1 C15 C16 123.9(4) . . ?
O1 C15 C14 115.5(4) . . ?
C16 C15 C14 120.6(4) . . ?
O2 C14 C13 125.0(4) . . ?
O2 C14 C15 116.0(4) . . ?
C13 C14 C15 119.0(4) . . ?
C10 N2 C6 117.1(3) . . ?
C14 O2 C22 118.6(4) . . ?
C15 O1 C23 117.2(4) . . ?
C17 C18 C19 117.1(4) . . ?
C17 C18 C10 119.4(3) . . ?
C19 C18 C10 123.4(3) . . ?
C20 C19 C18 119.7(4) 4_645 . ?
C20 C19 H19 120.2 4_645 . ?
C18 C19 H19 120.2 . . ?
C18 C17 C21 119.2(4) . 4_645 ?
C18 C17 H17 120.4 . . ?
C21 C17 H17 120.4 4_645 . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 N3 C20 115.9(3) . . ?
C21 N3 Cd1 122.2(3) . . ?
C20 N3 Cd1 121.6(3) . . ?
N3 C20 C19 124.0(4) . 4_655 ?
N3 C20 H20 118.0 . . ?
C19 C20 H20 118.0 4_655 . ?
N3 C21 C17 124.1(4) . 4_655 ?
N3 C21 H21 117.9 . . ?
C17 C21 H21 117.9 4_655 . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cd1 N1 C5 -84.9(3) 5_766 . . . ?
N3 Cd1 N1 C5 95.1(3) . . . . ?
I1 Cd1 N1 C5 6.4(3) . . . . ?
I1 Cd1 N1 C5 -173.6(3) 5_766 . . . ?
N3 Cd1 N1 C1 116.1(3) 5_766 . . . ?
N3 Cd1 N1 C1 -63.9(3) . . . . ?
I1 Cd1 N1 C1 -152.6(3) . . . . ?
I1 Cd1 N1 C1 27.4(3) 5_766 . . . ?
C7 C8 C11 C12 17.9(6) . . . . ?
C9 C8 C11 C12 -164.0(4) . . . . ?
C7 C8 C11 C16 -161.0(4) . . . . ?
C9 C8 C11 C16 17.1(6) . . . . ?
N2 C6 C7 C8 -1.7(6) . . . . ?
C3 C6 C7 C8 -178.2(3) . . . . ?
C9 C8 C7 C6 -0.7(5) . . . . ?
C11 C8 C7 C6 177.6(3) . . . . ?
N2 C10 C9 C8 -2.1(6) . . . . ?
C18 C10 C9 C8 174.8(3) . . . . ?
C7 C8 C9 C10 2.5(6) . . . . ?
C11 C8 C9 C10 -175.8(3) . . . . ?
C16 C11 C12 C13 0.3(7) . . . . ?
C8 C11 C12 C13 -178.6(4) . . . . ?
N2 C6 C3 C4 165.6(4) . . . . ?
C7 C6 C3 C4 -17.8(6) . . . . ?
N2 C6 C3 C2 -17.8(5) . . . . ?
C7 C6 C3 C2 158.9(4) . . . . ?
C12 C11 C16 C15 0.0(6) . . . . ?
C8 C11 C16 C15 178.9(4) . . . . ?
C5 N1 C1 C2 -1.9(7) . . . . ?
Cd1 N1 C1 C2 158.7(4) . . . . ?
N1 C1 C2 C3 -0.3(7) . . . . ?
C4 C3 C2 C1 2.6(6) . . . . ?
C6 C3 C2 C1 -174.3(4) . . . . ?
C1 N1 C5 C4 1.8(6) . . . . ?
Cd1 N1 C5 C4 -157.7(3) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
N1 C5 C4 C3 0.5(7) . . . . ?
C2 C3 C4 C5 -2.7(6) . . . . ?
C6 C3 C4 C5 174.1(4) . . . . ?
C11 C16 C15 O1 -179.0(4) . . . . ?
C11 C16 C15 C14 0.0(7) . . . . ?
C12 C13 C14 O2 -179.9(4) . . . . ?
C12 C13 C14 C15 0.5(7) . . . . ?
O1 C15 C14 O2 -0.7(6) . . . . ?
C16 C15 C14 O2 -179.9(4) . . . . ?
O1 C15 C14 C13 178.9(4) . . . . ?
C16 C15 C14 C13 -0.3(7) . . . . ?
C9 C10 N2 C6 -0.2(6) . . . . ?
C18 C10 N2 C6 -177.3(3) . . . . ?
C7 C6 N2 C10 2.2(6) . . . . ?
C3 C6 N2 C10 178.8(3) . . . . ?
C13 C14 O2 C22 3.1(7) . . . . ?
C15 C14 O2 C22 -177.3(4) . . . . ?
C16 C15 O1 C23 1.9(8) . . . . ?
C14 C15 O1 C23 -177.2(6) . . . . ?
N2 C10 C18 C17 21.6(6) . . . . ?
C9 C10 C18 C17 -155.6(5) . . . . ?
N2 C10 C18 C19 -161.5(4) . . . . ?
C9 C10 C18 C19 21.3(6) . . . . ?
C17 C18 C19 C20 0.3(7) . . . 4_645 ?
C10 C18 C19 C20 -176.7(4) . . . 4_645 ?
C19 C18 C17 C21 -0.6(8) . . . 4_645 ?
C10 C18 C17 C21 176.5(5) . . . 4_645 ?
N1 Cd1 N3 C21 159.8(4) 5_766 . . . ?
N1 Cd1 N3 C21 -20.2(4) . . . . ?
I1 Cd1 N3 C21 68.6(4) . . . . ?
I1 Cd1 N3 C21 -111.4(4) 5_766 . . . ?
N1 Cd1 N3 C20 -13.8(3) 5_766 . . . ?
N1 Cd1 N3 C20 166.2(3) . . . . ?
I1 Cd1 N3 C20 -105.1(3) . . . . ?
I1 Cd1 N3 C20 74.9(3) 5_766 . . . ?
C21 N3 C20 C19 0.6(7) . . . 4_655 ?
Cd1 N3 C20 C19 174.6(4) . . . 4_655 ?
C20 N3 C21 C17 -0.9(9) . . . 4_655 ?
Cd1 N3 C21 C17 -174.9(5) . . . 4_655 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.024
_refine_diff_density_min         -1.284
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 978707'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ups1728shi_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H38 Cl2 Co N6 O4'
_chemical_formula_sum            'C46 H38 Cl2 Co N6 O4'
_chemical_formula_weight         868.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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                   24.4845(18)
_cell_length_b                   11.8901(8)
_cell_length_c                   18.1106(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.564(4)
_cell_angle_gamma                90.00
_cell_volume                     4795.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    154
_cell_measurement_theta_min      1.83
_cell_measurement_theta_max      26.42

_exptl_crystal_description       cubic
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1796.0
_exptl_absorpt_coefficient_mu    0.514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36341
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         26.42
_reflns_number_total             4874
_reflns_number_gt                2840
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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. 

_platon_squeeze_details 
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.500  0.000  0.032       574       253 ' '
   2  1.000  0.500  0.745       574       253 ' '

;

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4874
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.2277
_refine_ls_wR_factor_gt          0.2150
_refine_ls_goodness_of_fit_ref   1.330
_refine_ls_restrained_S_all      1.330
_refine_ls_shift/su_max          0.002
_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
Co1 Co 0.0000 0.0000 0.0000 0.0408(3) Uani 1 2 d S . .
Cl1 Cl -0.04574(5) 0.14386(10) 0.05122(7) 0.0603(4) Uani 1 1 d . . .
C10 C 0.28791(18) -0.1441(3) 0.4601(2) 0.0414(10) Uani 1 1 d . . .
C9 C 0.29351(18) -0.0647(4) 0.5193(2) 0.0481(11) Uani 1 1 d . . .
H9 H 0.3266 -0.0672 0.5692 0.058 Uiso 1 1 calc R . .
C8 C 0.25039(19) 0.0180(4) 0.5049(2) 0.0472(11) Uani 1 1 d . . .
C18 C 0.3352(2) -0.2281(4) 0.4719(3) 0.0626(10) Uani 1 1 d . . .
C14 C 0.2658(2) 0.2854(4) 0.6714(3) 0.0531(12) Uani 1 1 d . . .
C11 C 0.25549(19) 0.1106(4) 0.5628(2) 0.0454(11) Uani 1 1 d . . .
C15 C 0.3167(2) 0.2235(4) 0.6780(3) 0.0612(14) Uani 1 1 d . . .
C3 C 0.14582(18) -0.0690(3) 0.2908(2) 0.0448(11) Uani 1 1 d . . .
C6 C 0.19711(17) -0.0689(3) 0.3737(2) 0.0426(10) Uani 1 1 d . . .
C7 C 0.20069(19) 0.0137(3) 0.4299(2) 0.0472(11) Uani 1 1 d . . .
H7 H 0.1700 0.0661 0.4175 0.057 Uiso 1 1 calc R . .
C16 C 0.3116(2) 0.1364(4) 0.6246(3) 0.0591(13) Uani 1 1 d . . .
H16 H 0.3454 0.0953 0.6298 0.071 Uiso 1 1 calc R . .
C4 C 0.0935(2) -0.0132(4) 0.2746(3) 0.0541(12) Uani 1 1 d . . .
H4 H 0.0868 0.0206 0.3164 0.065 Uiso 1 1 calc R . .
C2 C 0.1508(2) -0.1225(4) 0.2273(3) 0.0572(13) Uani 1 1 d . . .
H2 H 0.1848 -0.1652 0.2363 0.069 Uiso 1 1 calc R . .
C12 C 0.2069(2) 0.1744(4) 0.5552(3) 0.0585(13) Uani 1 1 d . . .
H12 H 0.1698 0.1601 0.5129 0.070 Uiso 1 1 calc R . .
C1 C 0.1059(2) -0.1140(4) 0.1497(3) 0.0575(13) Uani 1 1 d . . .
H1 H 0.1107 -0.1517 0.1077 0.069 Uiso 1 1 calc R . .
C5 C 0.0502(2) -0.0072(4) 0.1949(3) 0.0545(12) Uani 1 1 d . . .
H5 H 0.0151 0.0322 0.1854 0.065 Uiso 1 1 calc R . .
C19 C 0.3750(2) -0.2660(5) 0.5458(3) 0.0701(15) Uani 1 1 d . . .
H19 H 0.3729 -0.2399 0.5929 0.084 Uiso 1 1 calc R . .
C17 C 0.3424(2) -0.2694(4) 0.4054(3) 0.0626(10) Uani 1 1 d . . .
H17 H 0.3172 -0.2456 0.3534 0.075 Uiso 1 1 calc R . .
C22 C 0.0816(2) 0.1572(4) -0.0508(3) 0.0543(8) Uani 1 1 d . . .
H22 H 0.0563 0.1313 -0.1021 0.065 Uiso 1 1 calc R . .
C13 C 0.2123(2) 0.2597(4) 0.6095(3) 0.0603(13) Uani 1 1 d . . .
H13 H 0.1783 0.3007 0.6035 0.072 Uiso 1 1 calc R . .
C21 C 0.2266(3) 0.4271(5) 0.7270(4) 0.0921(19) Uani 1 1 d . . .
H21A H 0.2058 0.4651 0.6762 0.138 Uiso 1 1 calc R . .
H21B H 0.2403 0.4811 0.7703 0.138 Uiso 1 1 calc R . .
H21C H 0.1998 0.3748 0.7355 0.138 Uiso 1 1 calc R . .
C23 C 0.1132(3) 0.1543(5) 0.0835(3) 0.091(2) Uani 1 1 d . . .
H23 H 0.1107 0.1258 0.1298 0.109 Uiso 1 1 calc R . .
C20 C 0.4237(3) 0.2036(6) 0.7433(4) 0.1087(14) Uani 1 1 d . . .
H20A H 0.4225 0.1252 0.7554 0.163 Uiso 1 1 calc R . .
H20B H 0.4580 0.2381 0.7854 0.163 Uiso 1 1 calc R . .
H20C H 0.4265 0.2114 0.6923 0.163 Uiso 1 1 calc R . .
N1 N 0.24002(15) -0.1467(3) 0.3875(2) 0.0475(9) Uani 1 1 d . . .
N3 N 0.07323(16) 0.1171(3) 0.0124(2) 0.0543(8) Uani 1 1 d . . .
N2 N 0.05538(14) -0.0533(3) 0.1322(2) 0.0444(9) Uani 1 1 d . . .
O2 O 0.27600(16) 0.3689(3) 0.7257(2) 0.0690(10) Uani 1 1 d . . .
O1 O 0.36988(17) 0.2576(3) 0.7387(3) 0.1087(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N3 2.207(4) . ?
Co1 N3 2.207(4) 5 ?
Co1 N2 2.296(3) 5 ?
Co1 N2 2.296(3) . ?
Co1 Cl1 2.4298(11) 5 ?
Co1 Cl1 2.4298(11) . ?
C10 N1 1.351(5) . ?
C10 C9 1.392(6) . ?
C10 C18 1.476(6) . ?
C9 C8 1.386(6) . ?
C9 H9 0.9300 . ?
C8 C7 1.398(6) . ?
C8 C11 1.489(6) . ?
C18 C19 1.364(6) . ?
C18 C17 1.378(7) . ?
C14 O2 1.346(5) . ?
C14 C13 1.360(6) . ?
C14 C15 1.409(7) . ?
C11 C12 1.368(6) . ?
C11 C16 1.399(6) . ?
C15 O1 1.371(5) . ?
C15 C16 1.387(6) . ?
C3 C4 1.360(6) . ?
C3 C2 1.364(6) . ?
C3 C6 1.504(5) . ?
C6 N1 1.343(5) . ?
C6 C7 1.390(6) . ?
C7 H7 0.9300 . ?
C16 H16 0.9300 . ?
C4 C5 1.393(6) . ?
C4 H4 0.9300 . ?
C2 C1 1.382(6) . ?
C2 H2 0.9300 . ?
C12 C13 1.380(6) . ?
C12 H12 0.9300 . ?
C1 N2 1.352(5) . ?
C1 H1 0.9300 . ?
C5 N2 1.315(5) . ?
C5 H5 0.9300 . ?
C19 C22 1.374(7) 4_545 ?
C19 H19 0.9300 . ?
C17 C23 1.366(7) 4_545 ?
C17 H17 0.9300 . ?
C22 N3 1.332(6) . ?
C22 C19 1.374(7) 4 ?
C22 H22 0.9300 . ?
C13 H13 0.9300 . ?
C21 O2 1.402(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 N3 1.327(6) . ?
C23 C17 1.366(7) 4 ?
C23 H23 0.9300 . ?
C20 O1 1.437(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 Co1 N3 180.0 . 5 ?
N3 Co1 N2 91.99(13) . 5 ?
N3 Co1 N2 88.01(13) 5 5 ?
N3 Co1 N2 88.01(13) . . ?
N3 Co1 N2 91.99(13) 5 . ?
N2 Co1 N2 180.0 5 . ?
N3 Co1 Cl1 89.95(10) . 5 ?
N3 Co1 Cl1 90.05(10) 5 5 ?
N2 Co1 Cl1 87.84(9) 5 5 ?
N2 Co1 Cl1 92.16(9) . 5 ?
N3 Co1 Cl1 90.05(10) . . ?
N3 Co1 Cl1 89.95(10) 5 . ?
N2 Co1 Cl1 92.16(9) 5 . ?
N2 Co1 Cl1 87.84(9) . . ?
Cl1 Co1 Cl1 180.00(5) 5 . ?
N1 C10 C9 122.2(4) . . ?
N1 C10 C18 115.9(4) . . ?
C9 C10 C18 121.8(3) . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C8 C7 116.4(4) . . ?
C9 C8 C11 123.9(4) . . ?
C7 C8 C11 119.7(4) . . ?
C19 C18 C17 116.2(4) . . ?
C19 C18 C10 124.3(5) . . ?
C17 C18 C10 119.5(4) . . ?
O2 C14 C13 126.2(5) . . ?
O2 C14 C15 115.8(4) . . ?
C13 C14 C15 117.9(4) . . ?
C12 C11 C16 118.9(4) . . ?
C12 C11 C8 121.6(4) . . ?
C16 C11 C8 119.5(4) . . ?
O1 C15 C16 124.1(5) . . ?
O1 C15 C14 115.1(4) . . ?
C16 C15 C14 120.8(4) . . ?
C4 C3 C2 116.8(4) . . ?
C4 C3 C6 122.4(4) . . ?
C2 C3 C6 120.7(4) . . ?
N1 C6 C7 122.9(4) . . ?
N1 C6 C3 116.7(4) . . ?
C7 C6 C3 120.2(4) . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C15 C16 C11 119.7(4) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C11 C12 C13 121.0(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
N2 C1 C2 122.8(4) . . ?
N2 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
N2 C5 C4 124.6(4) . . ?
N2 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C18 C19 C22 120.1(5) . 4_545 ?
C18 C19 H19 119.9 . . ?
C22 C19 H19 119.9 4_545 . ?
C23 C17 C18 119.4(4) 4_545 . ?
C23 C17 H17 120.3 4_545 . ?
C18 C17 H17 120.3 . . ?
N3 C22 C19 124.9(4) . 4 ?
N3 C22 H22 117.6 . . ?
C19 C22 H22 117.6 4 . ?
C14 C13 C12 121.7(5) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C23 C17 125.8(5) . 4 ?
N3 C23 H23 117.1 . . ?
C17 C23 H23 117.1 4 . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 N1 C10 117.4(4) . . ?
C23 N3 C22 113.5(4) . . ?
C23 N3 Co1 123.3(4) . . ?
C22 N3 Co1 123.2(3) . . ?
C5 N2 C1 115.4(3) . . ?
C5 N2 Co1 124.0(3) . . ?
C1 N2 Co1 118.6(3) . . ?
C14 O2 C21 118.5(4) . . ?
C15 O1 C20 117.1(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C10 C9 C8 -2.0(7) . . . . ?
C18 C10 C9 C8 175.7(4) . . . . ?
C10 C9 C8 C7 2.6(7) . . . . ?
C10 C9 C8 C11 -175.3(4) . . . . ?
N1 C10 C18 C19 -156.1(5) . . . . ?
C9 C10 C18 C19 26.1(8) . . . . ?
N1 C10 C18 C17 26.7(7) . . . . ?
C9 C10 C18 C17 -151.2(5) . . . . ?
C9 C8 C11 C12 -164.7(5) . . . . ?
C7 C8 C11 C12 17.4(7) . . . . ?
C9 C8 C11 C16 17.8(7) . . . . ?
C7 C8 C11 C16 -160.0(4) . . . . ?
O2 C14 C15 O1 -0.5(7) . . . . ?
C13 C14 C15 O1 176.4(5) . . . . ?
O2 C14 C15 C16 -179.2(4) . . . . ?
C13 C14 C15 C16 -2.3(7) . . . . ?
C4 C3 C6 N1 164.8(4) . . . . ?
C2 C3 C6 N1 -17.6(6) . . . . ?
C4 C3 C6 C7 -19.5(6) . . . . ?
C2 C3 C6 C7 158.1(4) . . . . ?
N1 C6 C7 C8 -0.3(7) . . . . ?
C3 C6 C7 C8 -175.8(4) . . . . ?
C9 C8 C7 C6 -1.5(7) . . . . ?
C11 C8 C7 C6 176.5(4) . . . . ?
O1 C15 C16 C11 -177.7(5) . . . . ?
C14 C15 C16 C11 0.9(7) . . . . ?
C12 C11 C16 C15 1.7(7) . . . . ?
C8 C11 C16 C15 179.2(5) . . . . ?
C2 C3 C4 C5 -4.1(7) . . . . ?
C6 C3 C4 C5 173.6(4) . . . . ?
C4 C3 C2 C1 3.7(7) . . . . ?
C6 C3 C2 C1 -174.0(4) . . . . ?
C16 C11 C12 C13 -2.8(7) . . . . ?
C8 C11 C12 C13 179.8(4) . . . . ?
C3 C2 C1 N2 0.1(8) . . . . ?
C3 C4 C5 N2 0.7(8) . . . . ?
C17 C18 C19 C22 -1.3(8) . . . 4_545 ?
C10 C18 C19 C22 -178.6(5) . . . 4_545 ?
C19 C18 C17 C23 1.4(8) . . . 4_545 ?
C10 C18 C17 C23 178.9(5) . . . 4_545 ?
O2 C14 C13 C12 177.8(5) . . . . ?
C15 C14 C13 C12 1.3(7) . . . . ?
C11 C12 C13 C14 1.3(8) . . . . ?
C7 C6 N1 C10 1.1(6) . . . . ?
C3 C6 N1 C10 176.7(4) . . . . ?
C9 C10 N1 C6 0.0(6) . . . . ?
C18 C10 N1 C6 -177.8(4) . . . . ?
C17 C23 N3 C22 3.3(9) 4 . . . ?
C17 C23 N3 Co1 -176.8(5) 4 . . . ?
C19 C22 N3 C23 -3.1(8) 4 . . . ?
C19 C22 N3 Co1 177.0(4) 4 . . . ?
N2 Co1 N3 C23 158.6(5) 5 . . . ?
N2 Co1 N3 C23 -21.4(5) . . . . ?
Cl1 Co1 N3 C23 -113.6(5) 5 . . . ?
Cl1 Co1 N3 C23 66.4(5) . . . . ?
N2 Co1 N3 C22 -21.5(4) 5 . . . ?
N2 Co1 N3 C22 158.5(4) . . . . ?
Cl1 Co1 N3 C22 66.3(4) 5 . . . ?
Cl1 Co1 N3 C22 -113.7(4) . . . . ?
C4 C5 N2 C1 3.1(7) . . . . ?
C4 C5 N2 Co1 -160.2(4) . . . . ?
C2 C1 N2 C5 -3.5(7) . . . . ?
C2 C1 N2 Co1 160.7(4) . . . . ?
N3 Co1 N2 C5 92.5(4) . . . . ?
N3 Co1 N2 C5 -87.5(4) 5 . . . ?
Cl1 Co1 N2 C5 -177.7(3) 5 . . . ?
Cl1 Co1 N2 C5 2.3(3) . . . . ?
N3 Co1 N2 C1 -70.3(3) . . . . ?
N3 Co1 N2 C1 109.7(3) 5 . . . ?
Cl1 Co1 N2 C1 19.6(3) 5 . . . ?
Cl1 Co1 N2 C1 -160.4(3) . . . . ?
C13 C14 O2 C21 9.0(7) . . . . ?
C15 C14 O2 C21 -174.4(5) . . . . ?
C16 C15 O1 C20 4.0(9) . . . . ?
C14 C15 O1 C20 -174.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.110
_database_code_depnum_ccdc_archive 'CCDC 978708'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ups1540shi_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N3 O2'
_chemical_formula_sum            'C23 H19 N3 O2'
_chemical_formula_weight         369.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.4682(14)
_cell_length_b                   10.4331(17)
_cell_length_c                   10.7425(17)
_cell_angle_alpha                67.349(9)
_cell_angle_beta                 73.251(9)
_cell_angle_gamma                85.916(9)
_cell_volume                     936.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    132
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      26.42

_exptl_crystal_description       Cubic
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10452
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         26.42
_reflns_number_total             3579
_reflns_number_gt                2436
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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)+(0.1000P)²+0.1119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3579
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.11301(15) 0.84593(16) 0.67577(16) 0.0381(4) Uani 1 1 d . . .
C3 C 0.88566(18) 0.71334(19) 0.92135(19) 0.0379(4) Uani 1 1 d . . .
C4 C 1.00602(19) 0.7798(2) 0.9241(2) 0.0405(5) Uani 1 1 d . . .
H4 H 1.0123 0.7814 1.0083 0.049 Uiso 1 1 calc R . .
O1 O 0.46848(15) 0.37715(15) 1.41974(14) 0.0570(4) Uani 1 1 d . . .
C6 C 0.99665(18) 0.79192(19) 0.52995(19) 0.0379(4) Uani 1 1 d . . .
O2 O 0.37708(14) 0.52756(15) 1.20551(15) 0.0591(4) Uani 1 1 d . . .
C1 C 0.99359(18) 0.78729(19) 0.67122(19) 0.0365(4) Uani 1 1 d . . .
C16 C 0.77506(18) 0.62842(19) 1.05415(19) 0.0378(4) Uani 1 1 d . . .
C13 C 1.25311(19) 0.90501(19) 0.80147(19) 0.0378(4) Uani 1 1 d . . .
C17 C 0.62496(19) 0.62271(19) 1.0638(2) 0.0395(5) Uani 1 1 d . . .
H17 H 0.5918 0.6760 0.9867 0.047 Uiso 1 1 calc R . .
C2 C 0.87858(18) 0.72070(19) 0.79140(19) 0.0387(5) Uani 1 1 d . . .
H2 H 0.7974 0.6814 0.7846 0.046 Uiso 1 1 calc R . .
C5 C 1.11680(18) 0.84376(19) 0.8004(2) 0.0374(4) Uani 1 1 d . . .
C19 C 0.5750(2) 0.45699(19) 1.30343(19) 0.0410(5) Uani 1 1 d . . .
C18 C 0.52540(19) 0.53887(19) 1.1866(2) 0.0405(5) Uani 1 1 d . . .
C7 C 1.1087(2) 0.8647(2) 0.4121(2) 0.0463(5) Uani 1 1 d . . .
H7 H 1.1819 0.9133 0.4202 0.056 Uiso 1 1 calc R . .
C20 C 0.7226(2) 0.4629(2) 1.2942(2) 0.0462(5) Uani 1 1 d . . .
H20 H 0.7562 0.4095 1.3710 0.055 Uiso 1 1 calc R . .
C21 C 0.8210(2) 0.5477(2) 1.1711(2) 0.0459(5) Uani 1 1 d . . .
H21 H 0.9203 0.5509 1.1665 0.055 Uiso 1 1 calc R . .
N3 N 1.51603(19) 1.00026(19) 0.81583(19) 0.0569(5) Uani 1 1 d . . .
C10 C 0.8914(2) 0.7238(3) 0.5079(2) 0.0622(7) Uani 1 1 d . . .
H10 H 0.8124 0.6736 0.5827 0.075 Uiso 1 1 calc R . .
C8 C 1.1125(2) 0.8657(3) 0.2834(2) 0.0571(6) Uani 1 1 d . . .
H8 H 1.1896 0.9161 0.2065 0.069 Uiso 1 1 calc R . .
C9 C 0.9052(3) 0.7314(3) 0.3745(3) 0.0722(8) Uani 1 1 d . . .
H9 H 0.8326 0.6850 0.3629 0.087 Uiso 1 1 calc R . .
N2 N 1.01354(19) 0.7994(2) 0.26075(19) 0.0638(6) Uani 1 1 d . . .
C14 C 1.2512(2) 0.9767(2) 0.8863(2) 0.0454(5) Uani 1 1 d . . .
H14 H 1.1621 0.9939 0.9412 0.054 Uiso 1 1 calc R . .
C12 C 1.3905(2) 0.8850(2) 0.7220(2) 0.0493(5) Uani 1 1 d . . .
H12 H 1.3978 0.8396 0.6611 0.059 Uiso 1 1 calc R . .
C15 C 1.3837(2) 1.0226(2) 0.8888(2) 0.0543(6) Uani 1 1 d . . .
H15 H 1.3799 1.0724 0.9451 0.065 Uiso 1 1 calc R . .
C11 C 1.5161(2) 0.9326(2) 0.7337(2) 0.0568(6) Uani 1 1 d . . .
H11 H 1.6068 0.9163 0.6805 0.068 Uiso 1 1 calc R . .
C22 C 0.5143(3) 0.2966(2) 1.5423(2) 0.0673(7) Uani 1 1 d . . .
H22A H 0.5836 0.2306 1.5220 0.101 Uiso 1 1 calc R . .
H22B H 0.4298 0.2481 1.6179 0.101 Uiso 1 1 calc R . .
H22C H 0.5600 0.3571 1.5692 0.101 Uiso 1 1 calc R . .
C23 C 0.3162(2) 0.6304(2) 1.1055(3) 0.0665(7) Uani 1 1 d . . .
H23A H 0.3454 0.7211 1.0949 0.100 Uiso 1 1 calc R . .
H23B H 0.2104 0.6191 1.1374 0.100 Uiso 1 1 calc R . .
H23C H 0.3515 0.6204 1.0166 0.100 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 C5 1.341(2) . ?
N1 C1 1.345(2) . ?
C3 C4 1.389(2) . ?
C3 C2 1.389(3) . ?
C3 C16 1.488(2) . ?
C4 C5 1.387(2) . ?
C4 H4 0.9300 . ?
O1 C19 1.365(2) . ?
O1 C22 1.433(3) . ?
C6 C7 1.380(3) . ?
C6 C10 1.385(3) . ?
C6 C1 1.491(3) . ?
O2 C18 1.367(2) . ?
O2 C23 1.421(2) . ?
C1 C2 1.394(2) . ?
C16 C21 1.387(3) . ?
C16 C17 1.399(2) . ?
C13 C14 1.380(3) . ?
C13 C12 1.387(3) . ?
C13 C5 1.485(2) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C2 H2 0.9300 . ?
C19 C20 1.376(3) . ?
C19 C18 1.408(3) . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N3 C11 1.325(3) . ?
N3 C15 1.331(3) . ?
C10 C9 1.373(3) . ?
C10 H10 0.9300 . ?
C8 N2 1.330(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.328(3) . ?
C9 H9 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C12 C11 1.376(3) . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C11 H11 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C5 N1 C1 117.89(15) . . ?
C4 C3 C2 117.56(16) . . ?
C4 C3 C16 120.81(16) . . ?
C2 C3 C16 121.45(15) . . ?
C5 C4 C3 119.54(17) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C19 O1 C22 117.05(16) . . ?
C7 C6 C10 115.93(18) . . ?
C7 C6 C1 120.74(15) . . ?
C10 C6 C1 123.33(17) . . ?
C18 O2 C23 117.49(15) . . ?
N1 C1 C2 122.26(16) . . ?
N1 C1 C6 115.31(15) . . ?
C2 C1 C6 122.36(15) . . ?
C21 C16 C17 118.22(16) . . ?
C21 C16 C3 119.84(16) . . ?
C17 C16 C3 121.89(16) . . ?
C14 C13 C12 116.78(17) . . ?
C14 C13 C5 122.43(17) . . ?
C12 C13 C5 120.68(17) . . ?
C18 C17 C16 120.77(17) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C3 C2 C1 119.74(15) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
N1 C5 C4 122.88(15) . . ?
N1 C5 C13 116.03(15) . . ?
C4 C5 C13 120.93(16) . . ?
O1 C19 C20 125.02(17) . . ?
O1 C19 C18 115.60(16) . . ?
C20 C19 C18 119.37(16) . . ?
O2 C18 C17 124.66(17) . . ?
O2 C18 C19 115.44(16) . . ?
C17 C18 C19 119.91(16) . . ?
C8 C7 C6 120.34(18) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C19 C20 C21 120.19(17) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 121.53(17) . . ?
C20 C21 H21 119.2 . . ?
C16 C21 H21 119.2 . . ?
C11 N3 C15 115.76(17) . . ?
C9 C10 C6 119.25(19) . . ?
C9 C10 H10 120.4 . . ?
C6 C10 H10 120.4 . . ?
N2 C8 C7 124.5(2) . . ?
N2 C8 H8 117.7 . . ?
C7 C8 H8 117.7 . . ?
N2 C9 C10 125.3(2) . . ?
N2 C9 H9 117.3 . . ?
C10 C9 H9 117.3 . . ?
C9 N2 C8 114.61(19) . . ?
C13 C14 C15 119.14(19) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
N3 C15 C14 124.4(2) . . ?
N3 C15 H15 117.8 . . ?
C14 C15 H15 117.8 . . ?
N3 C11 C12 124.3(2) . . ?
N3 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 -3.3(3) . . . . ?
C16 C3 C4 C5 172.03(17) . . . . ?
C5 N1 C1 C2 -2.6(3) . . . . ?
C5 N1 C1 C6 -179.47(15) . . . . ?
C7 C6 C1 N1 -6.4(3) . . . . ?
C10 C6 C1 N1 172.71(19) . . . . ?
C7 C6 C1 C2 176.77(19) . . . . ?
C10 C6 C1 C2 -4.2(3) . . . . ?
C4 C3 C16 C21 -37.7(3) . . . . ?
C2 C3 C16 C21 137.45(19) . . . . ?
C4 C3 C16 C17 144.86(18) . . . . ?
C2 C3 C16 C17 -40.0(3) . . . . ?
C21 C16 C17 C18 0.0(3) . . . . ?
C3 C16 C17 C18 177.43(17) . . . . ?
C4 C3 C2 C1 3.1(3) . . . . ?
C16 C3 C2 C1 -172.24(17) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
C6 C1 C2 C3 176.53(17) . . . . ?
C1 N1 C5 C4 2.3(3) . . . . ?
C1 N1 C5 C13 177.81(16) . . . . ?
C3 C4 C5 N1 0.6(3) . . . . ?
C3 C4 C5 C13 -174.62(17) . . . . ?
C14 C13 C5 N1 144.98(18) . . . . ?
C12 C13 C5 N1 -38.9(3) . . . . ?
C14 C13 C5 C4 -39.4(3) . . . . ?
C12 C13 C5 C4 136.7(2) . . . . ?
C22 O1 C19 C20 1.8(3) . . . . ?
C22 O1 C19 C18 -177.65(18) . . . . ?
C23 O2 C18 C17 -14.9(3) . . . . ?
C23 O2 C18 C19 165.30(19) . . . . ?
C16 C17 C18 O2 179.63(17) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
O1 C19 C18 O2 0.1(2) . . . . ?
C20 C19 C18 O2 -179.41(17) . . . . ?
O1 C19 C18 C17 -179.73(17) . . . . ?
C20 C19 C18 C17 0.8(3) . . . . ?
C10 C6 C7 C8 -0.7(3) . . . . ?
C1 C6 C7 C8 178.45(18) . . . . ?
O1 C19 C20 C21 -179.83(17) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C16 -0.2(3) . . . . ?
C17 C16 C21 C20 0.4(3) . . . . ?
C3 C16 C21 C20 -177.08(18) . . . . ?
C7 C6 C10 C9 0.6(3) . . . . ?
C1 C6 C10 C9 -178.5(2) . . . . ?
C6 C7 C8 N2 -0.2(3) . . . . ?
C6 C10 C9 N2 0.3(4) . . . . ?
C10 C9 N2 C8 -1.1(4) . . . . ?
C7 C8 N2 C9 1.1(4) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C5 C13 C14 C15 175.61(18) . . . . ?
C14 C13 C12 C11 1.8(3) . . . . ?
C5 C13 C12 C11 -174.53(18) . . . . ?
C11 N3 C15 C14 2.0(3) . . . . ?
C13 C14 C15 N3 -1.3(3) . . . . ?
C15 N3 C11 C12 -0.7(3) . . . . ?
C13 C12 C11 N3 -1.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.98
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 978709'
