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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_azam_a3_01
#TrackingRef 'AZAM_A3_01.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N2 O2'
_chemical_formula_sum            'C19 H22 N2 O2'
_chemical_formula_weight         310.39

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121
_symmetry_space_group_name_Hall  P2ac2ab

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

_cell_length_a                   6.1281(3)
_cell_length_b                   15.9681(10)
_cell_length_c                   17.3110(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1693.95(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    15570
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.30

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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  'Stoe IPDS-2T'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18886
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3681
_reflns_number_gt                3333
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.1439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         3681
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
O1 O 0.93246(16) 0.22030(7) 0.64143(6) 0.0476(3) Uani 1 1 d . . .
H1O H 0.851(3) 0.2660(11) 0.6523(11) 0.061(5) Uiso 1 1 d . . .
O2 O 0.84251(17) 0.38500(7) 0.98860(6) 0.0488(3) Uani 1 1 d . . .
H2O H 0.769(4) 0.3780(13) 0.9400(14) 0.087(7) Uiso 1 1 d . . .
N1 N 0.60088(19) 0.32222(7) 0.64624(6) 0.0387(2) Uani 1 1 d . . .
N2 N 0.54026(18) 0.35285(6) 0.88923(6) 0.0366(2) Uani 1 1 d . . .
C1 C 0.8110(2) 0.17235(8) 0.59350(7) 0.0369(3) Uani 1 1 d . . .
C2 C 0.8997(2) 0.09823(8) 0.56436(8) 0.0448(3) Uani 1 1 d . . .
H2 H 1.0428 0.0818 0.5791 0.054 Uiso 1 1 calc R . .
C3 C 0.7813(3) 0.04896(9) 0.51459(9) 0.0495(4) Uani 1 1 d . . .
H3 H 0.8435 -0.0014 0.4954 0.059 Uiso 1 1 calc R . .
C4 C 0.5726(3) 0.07163(8) 0.49205(8) 0.0486(3) Uani 1 1 d . . .
H4 H 0.4927 0.0376 0.4570 0.058 Uiso 1 1 calc R . .
C5 C 0.4820(2) 0.14427(8) 0.52108(8) 0.0414(3) Uani 1 1 d . . .
H5 H 0.3385 0.1597 0.5060 0.050 Uiso 1 1 calc R . .
C6 C 0.5974(2) 0.19572(7) 0.57234(7) 0.0342(3) Uani 1 1 d . . .
C7 C 0.4952(2) 0.27158(8) 0.60293(7) 0.0354(3) Uani 1 1 d . . .
H7 H 0.3475 0.2834 0.5904 0.043 Uiso 1 1 calc R . .
C8 C 0.6943(2) 0.36692(7) 1.04393(7) 0.0360(3) Uani 1 1 d . . .
C9 C 0.7562(2) 0.37101(9) 1.12145(8) 0.0435(3) Uani 1 1 d . . .
H9 H 0.9010 0.3868 1.1346 0.052 Uiso 1 1 calc R . .
C10 C 0.6089(3) 0.35225(9) 1.17915(8) 0.0467(3) Uani 1 1 d . . .
H10 H 0.6534 0.3547 1.2317 0.056 Uiso 1 1 calc R . .
C11 C 0.3966(3) 0.32994(9) 1.16109(8) 0.0498(4) Uani 1 1 d . . .
H11 H 0.2954 0.3173 1.2010 0.060 Uiso 1 1 calc R . .
C12 C 0.3329(2) 0.32615(8) 1.08460(8) 0.0439(3) Uani 1 1 d . . .
H12 H 0.1872 0.3108 1.0724 0.053 Uiso 1 1 calc R . .
C13 C 0.4786(2) 0.34454(7) 1.02480(7) 0.0339(3) Uani 1 1 d . . .
C14 C 0.4069(2) 0.34023(7) 0.94454(7) 0.0348(3) Uani 1 1 d . . .
H14 H 0.2587 0.3278 0.9333 0.042 Uiso 1 1 calc R . .
C15 C 0.4928(2) 0.39772(8) 0.67477(7) 0.0418(3) Uani 1 1 d . . .
H15A H 0.3327 0.3904 0.6709 0.050 Uiso 1 1 calc R . .
H15B H 0.5342 0.4458 0.6418 0.050 Uiso 1 1 calc R . .
C16 C 0.5540(2) 0.41691(8) 0.75899(7) 0.0379(3) Uani 1 1 d . . .
C17 C 0.4669(2) 0.34517(8) 0.80957(7) 0.0384(3) Uani 1 1 d . . .
H17A H 0.3054 0.3455 0.8082 0.046 Uiso 1 1 calc R . .
H17B H 0.5174 0.2910 0.7883 0.046 Uiso 1 1 calc R . .
C18 C 0.4431(3) 0.49913(8) 0.78290(8) 0.0479(3) Uani 1 1 d . . .
H18A H 0.4978 0.5450 0.7506 0.072 Uiso 1 1 calc R . .
H18B H 0.4757 0.5110 0.8372 0.072 Uiso 1 1 calc R . .
H18C H 0.2849 0.4939 0.7761 0.072 Uiso 1 1 calc R . .
C19 C 0.8018(2) 0.42481(9) 0.76687(9) 0.0459(3) Uani 1 1 d . . .
H19A H 0.8570 0.4637 0.7277 0.069 Uiso 1 1 calc R . .
H19B H 0.8693 0.3697 0.7595 0.069 Uiso 1 1 calc R . .
H19C H 0.8378 0.4460 0.8184 0.069 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
O1 C1 1.3524(17) . ?
O1 H1O 0.91(2) . ?
O2 C8 1.3512(16) . ?
O2 H2O 0.96(2) . ?
N1 C7 1.2788(17) . ?
N1 C15 1.4616(16) . ?
N2 C14 1.2747(17) . ?
N2 C17 1.4556(16) . ?
C1 C2 1.3968(19) . ?
C1 C6 1.4094(18) . ?
C2 C3 1.374(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4008(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4626(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3961(19) . ?
C8 C13 1.4086(18) . ?
C9 C10 1.379(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3984(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.4588(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.5364(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C19 1.530(2) . ?
C16 C18 1.5353(17) . ?
C16 C17 1.5374(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C1 O1 H1O 106.3(12) . . ?
C8 O2 H2O 106.3(13) . . ?
C7 N1 C15 119.36(12) . . ?
C14 N2 C17 120.03(11) . . ?
O1 C1 C2 119.14(12) . . ?
O1 C1 C6 121.39(12) . . ?
C2 C1 C6 119.47(13) . . ?
C3 C2 C1 120.41(14) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.96(13) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.22(14) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.37(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.55(12) . . ?
C5 C6 C7 119.94(12) . . ?
C1 C6 C7 121.51(12) . . ?
N1 C7 C6 121.29(12) . . ?
N1 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
O2 C8 C9 119.26(12) . . ?
O2 C8 C13 121.21(12) . . ?
C9 C8 C13 119.54(12) . . ?
C10 C9 C8 120.53(13) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.50(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.53(13) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.33(14) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 118.58(12) . . ?
C12 C13 C14 120.19(12) . . ?
C8 C13 C14 121.24(11) . . ?
N2 C14 C13 120.99(12) . . ?
N2 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N1 C15 C16 111.98(11) . . ?
N1 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N1 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C19 C16 C18 110.18(12) . . ?
C19 C16 C15 110.10(11) . . ?
C18 C16 C15 108.55(11) . . ?
C19 C16 C17 110.81(11) . . ?
C18 C16 C17 109.27(11) . . ?
C15 C16 C17 107.88(10) . . ?
N2 C17 C16 111.69(10) . . ?
N2 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C1 C2 C3 -178.96(12) . . . . ?
C6 C1 C2 C3 0.93(19) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C1 0.65(18) . . . . ?
C4 C5 C6 C7 -179.04(12) . . . . ?
O1 C1 C6 C5 178.55(12) . . . . ?
C2 C1 C6 C5 -1.34(17) . . . . ?
O1 C1 C6 C7 -1.76(18) . . . . ?
C2 C1 C6 C7 178.35(11) . . . . ?
C15 N1 C7 C6 179.32(11) . . . . ?
C5 C6 C7 N1 -175.90(11) . . . . ?
C1 C6 C7 N1 4.42(18) . . . . ?
O2 C8 C9 C10 -179.48(12) . . . . ?
C13 C8 C9 C10 0.86(19) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C11 C12 C13 C8 0.26(19) . . . . ?
C11 C12 C13 C14 -179.86(13) . . . . ?
O2 C8 C13 C12 179.71(12) . . . . ?
C9 C8 C13 C12 -0.64(18) . . . . ?
O2 C8 C13 C14 -0.16(18) . . . . ?
C9 C8 C13 C14 179.48(11) . . . . ?
C17 N2 C14 C13 177.72(10) . . . . ?
C12 C13 C14 N2 -176.60(12) . . . . ?
C8 C13 C14 N2 3.27(17) . . . . ?
C7 N1 C15 C16 140.40(12) . . . . ?
N1 C15 C16 C19 56.51(15) . . . . ?
N1 C15 C16 C18 177.19(11) . . . . ?
N1 C15 C16 C17 -64.52(14) . . . . ?
C14 N2 C17 C16 136.46(12) . . . . ?
C19 C16 C17 N2 52.47(15) . . . . ?
C18 C16 C17 N2 -69.12(14) . . . . ?
C15 C16 C17 N2 173.06(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.026


_database_code_depnum_ccdc_archive 'CCDC 935900'
#######################################################################
#
#                 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_azam_a4_01
#TrackingRef 'azam_a4_01.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 N2 O5 U'
_chemical_formula_sum            'C20 H24 N2 O5 U'
_chemical_formula_weight         610.44

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'
U U -9.6767 9.6646 '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
_symmetry_space_group_name_Hall  -P2yn

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                   11.9341(6)
_cell_length_b                   12.2074(5)
_cell_length_c                   15.0211(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.791(4)
_cell_angle_gamma                90.00
_cell_volume                     2105.75(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    37623
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.36

_exptl_crystal_description       piece
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    7.740
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.1724
_exptl_absorpt_correction_T_max  0.4626
_exptl_absorpt_process_details   XShape

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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  'Stoe IPDS-2T'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29131
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         28.00
_reflns_number_total             5074
_reflns_number_gt                4517
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0208P)²+1.2339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5074
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0555
_refine_ls_wR_factor_gt          0.0533
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
U1 U 0.371903(9) 0.358792(8) 0.081764(8) 0.02547(5) Uani 1 1 d . . .
O1 O 0.2700(2) 0.24412(18) -0.02575(17) 0.0353(5) Uani 1 1 d . . .
O2 O 0.4779(2) 0.51812(17) 0.12087(16) 0.0318(5) Uani 1 1 d . . .
O3 O 0.2468(2) 0.4206(2) 0.10373(18) 0.0386(5) Uani 1 1 d . . .
O4 O 0.49938(19) 0.29757(17) 0.06408(16) 0.0321(5) Uani 1 1 d . . .
O5 O 0.3328(2) 0.46939(19) -0.06122(17) 0.0345(5) Uani 1 1 d . . .
H5O H 0.385(3) 0.474(3) -0.078(3) 0.043(12) Uiso 1 1 d . . .
N1 N 0.3225(2) 0.1826(2) 0.1589(2) 0.0317(6) Uani 1 1 d . . .
N2 N 0.4801(2) 0.36220(19) 0.2553(2) 0.0283(6) Uani 1 1 d . . .
C1 C 0.2917(3) 0.1404(2) -0.0430(3) 0.0319(7) Uani 1 1 d . . .
C2 C 0.2957(3) 0.1085(3) -0.1311(3) 0.0401(8) Uani 1 1 d . . .
H2 H 0.2874 0.1618 -0.1785 0.048 Uiso 1 1 calc R . .
C3 C 0.3119(4) -0.0010(3) -0.1500(3) 0.0517(10) Uani 1 1 d . . .
H3 H 0.3161 -0.0216 -0.2100 0.062 Uiso 1 1 calc R . .
C4 C 0.3218(4) -0.0804(3) -0.0826(3) 0.0572(11) Uani 1 1 d . . .
H4 H 0.3309 -0.1551 -0.0967 0.069 Uiso 1 1 calc R . .
C5 C 0.3185(4) -0.0505(3) 0.0051(3) 0.0507(10) Uani 1 1 d . . .
H5 H 0.3247 -0.1054 0.0511 0.061 Uiso 1 1 calc R . .
C6 C 0.3060(3) 0.0609(3) 0.0279(3) 0.0372(7) Uani 1 1 d . . .
C7 C 0.3024(3) 0.0880(3) 0.1203(3) 0.0375(7) Uani 1 1 d . . .
H7 H 0.2834 0.0305 0.1563 0.045 Uiso 1 1 calc R . .
C8 C 0.4790(3) 0.5919(2) 0.1863(2) 0.0285(6) Uani 1 1 d . . .
C9 C 0.4755(3) 0.7046(2) 0.1652(2) 0.0344(7) Uani 1 1 d . . .
H9 H 0.4701 0.7276 0.1038 0.041 Uiso 1 1 calc R . .
C10 C 0.4796(3) 0.7817(3) 0.2330(2) 0.0364(7) Uani 1 1 d . . .
H10 H 0.4766 0.8573 0.2175 0.044 Uiso 1 1 calc R . .
C11 C 0.4882(3) 0.7511(3) 0.3240(3) 0.0379(8) Uani 1 1 d . . .
H11 H 0.4893 0.8049 0.3699 0.045 Uiso 1 1 calc R . .
C12 C 0.4952(3) 0.6415(3) 0.3462(3) 0.0358(8) Uani 1 1 d . . .
H12 H 0.5044 0.6201 0.4086 0.043 Uiso 1 1 calc R . .
C13 C 0.4891(3) 0.5605(2) 0.2785(2) 0.0292(6) Uani 1 1 d . . .
C14 C 0.5089(3) 0.4463(2) 0.3076(2) 0.0303(6) Uani 1 1 d . . .
H14 H 0.5466 0.4332 0.3710 0.036 Uiso 1 1 calc R . .
C15 C 0.3109(3) 0.1941(3) 0.2535(2) 0.0354(7) Uani 1 1 d . . .
H15A H 0.2606 0.1345 0.2654 0.043 Uiso 1 1 calc R . .
H15B H 0.2720 0.2645 0.2585 0.043 Uiso 1 1 calc R . .
C16 C 0.4277(3) 0.1903(3) 0.3277(2) 0.0335(7) Uani 1 1 d . . .
C17 C 0.5210(3) 0.2552(2) 0.2967(2) 0.0304(7) Uani 1 1 d . . .
H17A H 0.5889 0.2669 0.3508 0.036 Uiso 1 1 calc R . .
H17B H 0.5475 0.2110 0.2510 0.036 Uiso 1 1 calc R . .
C18 C 0.4726(3) 0.0732(3) 0.3465(3) 0.0459(9) Uani 1 1 d . . .
H18A H 0.5469 0.0736 0.3946 0.069 Uiso 1 1 calc R . .
H18B H 0.4839 0.0415 0.2896 0.069 Uiso 1 1 calc R . .
H18C H 0.4158 0.0293 0.3673 0.069 Uiso 1 1 calc R . .
C19 C 0.4104(4) 0.2397(3) 0.4165(3) 0.0510(10) Uani 1 1 d . . .
H19A H 0.3836 0.3156 0.4050 0.076 Uiso 1 1 calc R . .
H19B H 0.4843 0.2382 0.4651 0.076 Uiso 1 1 calc R . .
H19C H 0.3520 0.1969 0.4365 0.076 Uiso 1 1 calc R . .
C20 C 0.2698(3) 0.5713(3) -0.0734(3) 0.0422(8) Uani 1 1 d . . .
H20A H 0.1945 0.5604 -0.0602 0.063 Uiso 1 1 calc R . .
H20B H 0.2569 0.5966 -0.1373 0.063 Uiso 1 1 calc R . .
H20C H 0.3149 0.6263 -0.0310 0.063 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
U1 O4 1.779(2) . ?
U1 O3 1.782(2) . ?
U1 O1 2.231(2) . ?
U1 O2 2.308(2) . ?
U1 O5 2.472(2) . ?
U1 N2 2.575(3) . ?
U1 N1 2.586(3) . ?
O1 C1 1.331(4) . ?
O2 C8 1.331(4) . ?
O5 C20 1.440(4) . ?
O5 H5O 0.74(4) . ?
N1 C7 1.286(4) . ?
N1 C15 1.472(4) . ?
N2 C14 1.282(4) . ?
N2 C17 1.472(4) . ?
C1 C2 1.394(5) . ?
C1 C6 1.416(5) . ?
C2 C3 1.391(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.421(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.439(5) . ?
C7 H7 0.9500 . ?
C8 C13 1.410(5) . ?
C8 C9 1.410(4) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.406(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.460(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.530(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.526(5) . ?
C16 C19 1.529(5) . ?
C16 C17 1.539(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O4 U1 O3 177.96(11) . . ?
O4 U1 O1 87.02(9) . . ?
O3 U1 O1 94.64(10) . . ?
O4 U1 O2 87.71(9) . . ?
O3 U1 O2 91.43(9) . . ?
O1 U1 O2 150.02(8) . . ?
O4 U1 O5 93.81(9) . . ?
O3 U1 O5 87.72(10) . . ?
O1 U1 O5 77.11(8) . . ?
O2 U1 O5 73.82(8) . . ?
O4 U1 N2 86.80(9) . . ?
O3 U1 N2 91.17(10) . . ?
O1 U1 N2 140.11(8) . . ?
O2 U1 N2 68.87(8) . . ?
O5 U1 N2 142.63(8) . . ?
O4 U1 N1 91.49(9) . . ?
O3 U1 N1 87.97(10) . . ?
O1 U1 N1 69.94(9) . . ?
O2 U1 N1 139.72(8) . . ?
O5 U1 N1 146.28(8) . . ?
N2 U1 N1 70.88(8) . . ?
C1 O1 U1 129.8(2) . . ?
C8 O2 U1 130.76(18) . . ?
C20 O5 U1 123.4(2) . . ?
C20 O5 H5O 110(3) . . ?
U1 O5 H5O 112(3) . . ?
C7 N1 C15 117.7(3) . . ?
C7 N1 U1 125.6(2) . . ?
C15 N1 U1 116.5(2) . . ?
C14 N2 C17 116.7(3) . . ?
C14 N2 U1 127.6(2) . . ?
C17 N2 U1 115.51(19) . . ?
O1 C1 C2 120.6(3) . . ?
O1 C1 C6 119.7(3) . . ?
C2 C1 C6 119.6(3) . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.3(4) . . ?
C1 C6 C7 122.6(3) . . ?
C5 C6 C7 119.0(3) . . ?
N1 C7 C6 126.2(3) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
O2 C8 C13 121.5(3) . . ?
O2 C8 C9 120.0(3) . . ?
C13 C8 C9 118.4(3) . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 119.5(3) . . ?
C12 C13 C14 118.8(3) . . ?
C8 C13 C14 121.1(3) . . ?
N2 C14 C13 125.9(3) . . ?
N2 C14 H14 117.0 . . ?
C13 C14 H14 117.0 . . ?
N1 C15 C16 113.2(3) . . ?
N1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C18 C16 C19 109.4(3) . . ?
C18 C16 C15 111.5(3) . . ?
C19 C16 C15 108.1(3) . . ?
C18 C16 C17 107.0(3) . . ?
C19 C16 C17 110.0(3) . . ?
C15 C16 C17 110.8(3) . . ?
N2 C17 C16 113.6(3) . . ?
N2 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
N2 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O4 U1 O1 C1 36.7(3) . . . . ?
O3 U1 O1 C1 -142.1(3) . . . . ?
O2 U1 O1 C1 116.9(3) . . . . ?
O5 U1 O1 C1 131.3(3) . . . . ?
N2 U1 O1 C1 -44.7(3) . . . . ?
N1 U1 O1 C1 -55.9(3) . . . . ?
O4 U1 O2 C8 -140.5(3) . . . . ?
O3 U1 O2 C8 37.7(3) . . . . ?
O1 U1 O2 C8 139.5(3) . . . . ?
O5 U1 O2 C8 124.9(3) . . . . ?
N2 U1 O2 C8 -53.0(3) . . . . ?
N1 U1 O2 C8 -50.9(3) . . . . ?
O4 U1 O5 C20 -153.7(3) . . . . ?
O3 U1 O5 C20 25.0(3) . . . . ?
O1 U1 O5 C20 120.3(3) . . . . ?
O2 U1 O5 C20 -67.2(2) . . . . ?
N2 U1 O5 C20 -64.0(3) . . . . ?
N1 U1 O5 C20 107.9(3) . . . . ?
O4 U1 N1 C7 -60.7(3) . . . . ?
O3 U1 N1 C7 121.3(3) . . . . ?
O1 U1 N1 C7 25.6(2) . . . . ?
O2 U1 N1 C7 -148.9(2) . . . . ?
O5 U1 N1 C7 38.4(3) . . . . ?
N2 U1 N1 C7 -146.8(3) . . . . ?
O4 U1 N1 C15 122.6(2) . . . . ?
O3 U1 N1 C15 -55.4(2) . . . . ?
O1 U1 N1 C15 -151.1(2) . . . . ?
O2 U1 N1 C15 34.4(3) . . . . ?
O5 U1 N1 C15 -138.3(2) . . . . ?
N2 U1 N1 C15 36.5(2) . . . . ?
O4 U1 N2 C14 117.5(3) . . . . ?
O3 U1 N2 C14 -62.4(3) . . . . ?
O1 U1 N2 C14 -161.0(2) . . . . ?
O2 U1 N2 C14 28.7(3) . . . . ?
O5 U1 N2 C14 25.4(3) . . . . ?
N1 U1 N2 C14 -149.8(3) . . . . ?
O4 U1 N2 C17 -57.5(2) . . . . ?
O3 U1 N2 C17 122.7(2) . . . . ?
O1 U1 N2 C17 24.0(3) . . . . ?
O2 U1 N2 C17 -146.2(2) . . . . ?
O5 U1 N2 C17 -149.54(18) . . . . ?
N1 U1 N2 C17 35.24(19) . . . . ?
U1 O1 C1 C2 -125.5(3) . . . . ?
U1 O1 C1 C6 57.1(4) . . . . ?
O1 C1 C2 C3 -176.4(3) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
O1 C1 C6 C5 174.4(3) . . . . ?
C2 C1 C6 C5 -3.0(5) . . . . ?
O1 C1 C6 C7 -2.4(5) . . . . ?
C2 C1 C6 C7 -179.8(3) . . . . ?
C4 C5 C6 C1 2.8(6) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
C15 N1 C7 C6 178.2(3) . . . . ?
U1 N1 C7 C6 1.5(5) . . . . ?
C1 C6 C7 N1 -23.0(5) . . . . ?
C5 C6 C7 N1 160.2(3) . . . . ?
U1 O2 C8 C13 48.7(4) . . . . ?
U1 O2 C8 C9 -134.2(3) . . . . ?
O2 C8 C9 C10 -178.3(3) . . . . ?
C13 C8 C9 C10 -1.1(5) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C9 C10 C11 C12 1.4(5) . . . . ?
C10 C11 C12 C13 -2.6(5) . . . . ?
C11 C12 C13 C8 1.9(5) . . . . ?
C11 C12 C13 C14 173.8(3) . . . . ?
O2 C8 C13 C12 177.1(3) . . . . ?
C9 C8 C13 C12 0.0(4) . . . . ?
O2 C8 C13 C14 5.4(5) . . . . ?
C9 C8 C13 C14 -171.7(3) . . . . ?
C17 N2 C14 C13 172.8(3) . . . . ?
U1 N2 C14 C13 -2.0(5) . . . . ?
C12 C13 C14 N2 162.5(3) . . . . ?
C8 C13 C14 N2 -25.8(5) . . . . ?
C7 N1 C15 C16 99.9(3) . . . . ?
U1 N1 C15 C16 -83.1(3) . . . . ?
N1 C15 C16 C18 -78.2(3) . . . . ?
N1 C15 C16 C19 161.5(3) . . . . ?
N1 C15 C16 C17 40.9(4) . . . . ?
C14 N2 C17 C16 100.0(3) . . . . ?
U1 N2 C17 C16 -84.5(3) . . . . ?
C18 C16 C17 N2 166.5(3) . . . . ?
C19 C16 C17 N2 -74.8(4) . . . . ?
C15 C16 C17 N2 44.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.107


_database_code_depnum_ccdc_archive 'CCDC 935908'
