# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ic15835

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '[2a]I2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H36 I2 N8 O4'
_chemical_formula_weight         898.53

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'
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   C2/c

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

_cell_length_a                   21.0444(10)
_cell_length_b                   12.4275(5)
_cell_length_c                   15.2824(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.665(2)
_cell_angle_gamma                90.00
_cell_volume                     3632.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11333
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1784
_exptl_absorpt_coefficient_mu    1.782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'SORTAV, (Blessing,1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11333
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3201
_reflns_number_gt                2288
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'NONIUS COLLECT'
_computing_cell_refinement       DENZO-SMN
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0350P)²+9.5697P] 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         3201
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.285703(19) 0.27483(3) 0.37543(2) 0.04152(15) Uani 1 1 d . . .
O1 O 0.4907(2) 0.1792(3) 0.5052(2) 0.0386(9) Uani 1 1 d . . .
O2 O 0.41632(19) 0.3978(3) 0.2396(2) 0.0358(9) Uani 1 1 d . . .
N1 N 0.4642(2) 0.3120(3) 0.3884(3) 0.0281(10) Uani 1 1 d . . .
N2 N 0.3977(2) -0.1192(4) 0.2007(3) 0.0312(10) Uani 1 1 d . . .
N3 N 0.3596(2) -0.0136(4) 0.0741(3) 0.0340(11) Uani 1 1 d . . .
C1 C 0.3672(3) -0.1151(5) 0.1043(3) 0.0354(13) Uani 1 1 d . . .
H1 H 0.3529 -0.1762 0.0633 0.042 Uiso 1 1 calc R . .
C2 C 0.4082(3) -0.0132(4) 0.2349(3) 0.0276(11) Uani 1 1 d . . .
C3 C 0.4375(3) 0.0266(4) 0.3294(3) 0.0296(12) Uani 1 1 d . . .
H3 H 0.4538 -0.0185 0.3846 0.036 Uiso 1 1 calc R . .
C4 C 0.4405(3) 0.1375(4) 0.3345(3) 0.0271(11) Uani 1 1 d . . .
C5 C 0.4168(3) 0.2034(4) 0.2537(3) 0.0292(12) Uani 1 1 d . . .
C6 C 0.3875(3) 0.1660(4) 0.1604(3) 0.0316(12) Uani 1 1 d . . .
H6 H 0.3714 0.2120 0.1058 0.038 Uiso 1 1 calc R . .
C7 C 0.3837(3) 0.0540(4) 0.1539(3) 0.0311(12) Uani 1 1 d . . .
C8 C 0.4684(3) 0.2069(4) 0.4222(3) 0.0321(13) Uani 1 1 d . . .
C9 C 0.4301(3) 0.3166(4) 0.2862(3) 0.0289(12) Uani 1 1 d . . .
C10 C 0.5262(3) 0.4816(4) 0.4315(3) 0.0329(13) Uani 1 1 d . . .
H10 H 0.5441 0.4690 0.3847 0.040 Uiso 1 1 calc R . .
C11 C 0.4831(3) 0.4071(4) 0.4463(3) 0.0286(12) Uani 1 1 d . . .
C12 C 0.4571(3) 0.4253(4) 0.5145(3) 0.0324(12) Uani 1 1 d . . .
H12 H 0.4276 0.3733 0.5242 0.039 Uiso 1 1 calc R . .
C13 C 0.4105(3) -0.2175(4) 0.2610(3) 0.0361(13) Uani 1 1 d . . .
H13A H 0.3745 -0.2224 0.2868 0.043 Uiso 1 1 calc R . .
H13B H 0.4567 -0.2115 0.3164 0.043 Uiso 1 1 calc R . .
C14 C 0.4087(3) -0.3192(5) 0.2054(4) 0.0429(14) Uani 1 1 d . . .
H14A H 0.3616 -0.3292 0.1543 0.064 Uiso 1 1 calc R . .
H14B H 0.4208 -0.3810 0.2491 0.064 Uiso 1 1 calc R . .
H14C H 0.4424 -0.3131 0.1768 0.064 Uiso 1 1 calc R . .
C15 C 0.3282(3) 0.0214(5) -0.0279(3) 0.0420(15) Uani 1 1 d . . .
H15A H 0.3313 -0.0379 -0.0691 0.050 Uiso 1 1 calc R . .
H15B H 0.3549 0.0833 -0.0359 0.050 Uiso 1 1 calc R . .
C16 C 0.2525(3) 0.0534(5) -0.0599(4) 0.0547(17) Uani 1 1 d . . .
H16A H 0.2260 -0.0077 -0.0519 0.082 Uiso 1 1 calc R . .
H16B H 0.2330 0.0747 -0.1279 0.082 Uiso 1 1 calc R . .
H16C H 0.2494 0.1140 -0.0208 0.082 Uiso 1 1 calc R . .
N4 N 0.3455(4) 0.2845(5) -0.0501(4) 0.0713(18) Uani 1 1 d . . .
C17 C 0.3260(4) 0.3510(5) -0.1056(4) 0.0514(17) Uani 1 1 d . . .
C18 C 0.3022(5) 0.4357(6) -0.1770(5) 0.077(2) Uani 1 1 d . . .
H18A H 0.3423 0.4673 -0.1843 0.116 Uiso 1 1 calc R . .
H18B H 0.2785 0.4915 -0.1562 0.116 Uiso 1 1 calc R . .
H18C H 0.2695 0.4058 -0.2387 0.116 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 C8 1.204(6) . ?
O2 C9 1.200(6) . ?
N1 C8 1.395(7) . ?
N1 C9 1.422(6) . ?
N1 C11 1.429(6) . ?
N2 C1 1.340(6) . ?
N2 C2 1.401(6) . ?
N2 C13 1.485(6) . ?
N3 C1 1.329(7) . ?
N3 C7 1.391(6) . ?
N3 C15 1.482(6) . ?
C2 C3 1.402(7) . ?
C2 C7 1.402(7) . ?
C3 C4 1.380(7) . ?
C4 C5 1.389(7) . ?
C4 C8 1.493(7) . ?
C5 C6 1.377(7) . ?
C5 C9 1.479(7) . ?
C6 C7 1.395(7) . ?
C10 C11 1.379(7) . ?
C10 C12 1.379(7) 5_666 ?
C11 C12 1.382(7) . ?
C12 C10 1.379(7) 5_666 ?
C13 C14 1.515(7) . ?
C15 C16 1.511(8) . ?
N4 C17 1.131(8) . ?
C17 C18 1.447(9) . ?

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
C8 N1 C9 111.6(4) . . ?
C8 N1 C11 126.0(4) . . ?
C9 N1 C11 122.0(4) . . ?
C1 N2 C2 107.6(4) . . ?
C1 N2 C13 126.4(4) . . ?
C2 N2 C13 125.6(4) . . ?
C1 N3 C7 108.8(4) . . ?
C1 N3 C15 125.5(4) . . ?
C7 N3 C15 125.7(4) . . ?
N3 C1 N2 110.6(5) . . ?
N2 C2 C3 130.5(5) . . ?
N2 C2 C7 106.8(4) . . ?
C3 C2 C7 122.8(5) . . ?
C4 C3 C2 113.6(4) . . ?
C3 C4 C5 123.2(4) . . ?
C3 C4 C8 128.2(4) . . ?
C5 C4 C8 108.6(4) . . ?
C6 C5 C4 124.1(5) . . ?
C6 C5 C9 127.5(5) . . ?
C4 C5 C9 108.4(4) . . ?
C5 C6 C7 113.5(5) . . ?
N3 C7 C6 130.9(5) . . ?
N3 C7 C2 106.2(4) . . ?
C6 C7 C2 122.8(4) . . ?
O1 C8 N1 126.5(5) . . ?
O1 C8 C4 128.0(5) . . ?
N1 C8 C4 105.6(4) . . ?
O2 C9 N1 124.8(5) . . ?
O2 C9 C5 129.6(4) . . ?
N1 C9 C5 105.6(4) . . ?
C11 C10 C12 119.1(5) . 5_666 ?
C10 C11 C12 120.5(5) . . ?
C10 C11 N1 119.1(4) . . ?
C12 C11 N1 120.4(5) . . ?
C10 C12 C11 120.4(5) 5_666 . ?
N2 C13 C14 112.4(4) . . ?
N3 C15 C16 111.5(5) . . ?
N4 C17 C18 179.1(8) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.105
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile, ether'
_database_code_depnum_ccdc_archive 'CCDC 1020160'
#######################################################################
#
#                 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_ic16141

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2a-(NiCpI)2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H40 Cl6 I2 N6 Ni2 O4'
_chemical_formula_weight         1300.74

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'
Ni Ni 0.3393 1.1124 '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   P2(1)/c

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

_cell_length_a                   9.0998(3)
_cell_length_b                   24.2692(7)
_cell_length_c                   11.5148(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.2740(13)
_cell_angle_gamma                90.00
_cell_volume                     2400.45(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12336
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1284
_exptl_absorpt_coefficient_mu    2.453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12336
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4218
_reflns_number_gt                2627
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'NONIUS COLLECT'
_computing_cell_refinement       DENZO-SMN
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. The structure restraints 
 are applied to the disordered Cp ring. The distance restraints are used to 
 the disordered CHCl3 solvent. 
;

_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)+(0.1420P)²+20.3435P] 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         4218
_refine_ls_number_parameters     288
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1690
_refine_ls_R_factor_gt           0.1254
_refine_ls_wR_factor_ref         0.3470
_refine_ls_wR_factor_gt          0.3282
_refine_ls_goodness_of_fit_ref   1.333
_refine_ls_restrained_S_all      1.340
_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
Ni1 Ni 0.34540(19) 0.16136(7) 0.61510(15) 0.0355(5) Uani 1 1 d . . .
I1 I 0.43707(19) 0.25052(6) 0.60610(14) 0.0874(7) Uani 1 1 d . A .
O3 O 0.6099(11) 0.0725(4) -0.0017(8) 0.049(3) Uani 1 1 d . A .
O4 O 0.9973(9) 0.0070(4) 0.3334(7) 0.0310(19) Uani 1 1 d . . .
N1 N 0.8249(12) 0.0340(4) 0.1446(8) 0.031(2) Uani 1 1 d . A .
N2 N 0.4089(11) 0.1380(4) 0.3904(8) 0.025(2) Uani 1 1 d . . .
N3 N 0.5849(11) 0.1017(4) 0.5489(8) 0.026(2) Uani 1 1 d . . .
C1 C 0.4531(15) 0.1318(5) 0.5155(11) 0.033(3) Uani 1 1 d . A .
C2 C 0.5121(14) 0.1125(5) 0.3448(11) 0.028(3) Uani 1 1 d . A .
C3 C 0.5152(14) 0.1058(5) 0.2236(11) 0.031(3) Uani 1 1 d . . .
H3 H 0.4363 0.1202 0.1537 0.037 Uiso 1 1 calc R A .
C4 C 0.6407(14) 0.0771(5) 0.2145(11) 0.030(3) Uani 1 1 d . A .
C5 C 0.7568(12) 0.0551(5) 0.3171(10) 0.026(3) Uani 1 1 d . . .
C6 C 0.7549(12) 0.0607(5) 0.4365(10) 0.023(2) Uani 1 1 d . A .
H6 H 0.8341 0.0461 0.5058 0.027 Uiso 1 1 calc R . .
C7 C 0.6288(13) 0.0893(5) 0.4463(10) 0.025(3) Uani 1 1 d . A .
C8 C 0.6787(14) 0.0630(5) 0.1029(11) 0.033(3) Uani 1 1 d . . .
C9 C 0.8792(14) 0.0280(5) 0.2754(10) 0.027(3) Uani 1 1 d . A .
C10 C 0.9489(14) 0.0542(5) -0.0074(10) 0.030(3) Uani 1 1 d . . .
H10 H 0.9145 0.0913 -0.0107 0.036 Uiso 1 1 calc R . .
C11 C 0.9091(14) 0.0163(5) 0.0691(10) 0.030(3) Uani 1 1 d . . .
C12 C 0.9638(14) -0.0383(5) 0.0766(10) 0.032(3) Uani 1 1 d . . .
H12 H 0.9396 -0.0639 0.1301 0.039 Uiso 1 1 calc R . .
C13 C 0.2706(15) 0.1696(5) 0.3157(12) 0.035(3) Uani 1 1 d . A .
H13A H 0.2991 0.1937 0.2571 0.043 Uiso 1 1 calc R . .
H13B H 0.2333 0.1933 0.3702 0.043 Uiso 1 1 calc R . .
C14 C 0.1413(18) 0.1302(7) 0.2452(15) 0.059(4) Uani 1 1 d . . .
H14A H 0.1850 0.1012 0.2072 0.089 Uiso 1 1 calc R A .
H14B H 0.0617 0.1506 0.1811 0.089 Uiso 1 1 calc R . .
H14C H 0.0942 0.1136 0.3020 0.089 Uiso 1 1 calc R . .
C15 C 0.6696(14) 0.0839(5) 0.6735(10) 0.029(3) Uani 1 1 d . A .
H15A H 0.6375 0.1066 0.7326 0.035 Uiso 1 1 calc R . .
H15B H 0.7826 0.0895 0.6907 0.035 Uiso 1 1 calc R . .
C16 C 0.6378(14) 0.0231(5) 0.6908(12) 0.036(3) Uani 1 1 d . . .
H16A H 0.5270 0.0181 0.6795 0.053 Uiso 1 1 calc R A .
H16B H 0.7002 0.0114 0.7739 0.053 Uiso 1 1 calc R . .
H16C H 0.6656 0.0009 0.6301 0.053 Uiso 1 1 calc R . .
C17 C 0.2131(18) 0.0923(6) 0.6283(14) 0.027(3) Uiso 0.788(7) 1 d PD A 1
H17A H 0.2164 0.0598 0.5831 0.032 Uiso 0.788(7) 1 calc PR A 1
C18 C 0.318(2) 0.1054(9) 0.7536(19) 0.043(4) Uiso 0.788(7) 1 d PD A 1
H18A H 0.3947 0.0818 0.8060 0.052 Uiso 0.788(7) 1 calc PR A 1
C19 C 0.283(2) 0.1583(9) 0.7803(18) 0.044(4) Uiso 0.788(7) 1 d PD A 1
H19A H 0.3354 0.1782 0.8533 0.053 Uiso 0.788(7) 1 calc PR A 1
C20 C 0.155(2) 0.1780(7) 0.6794(19) 0.043(5) Uiso 0.788(7) 1 d PD A 1
H20A H 0.1075 0.2132 0.6732 0.052 Uiso 0.788(7) 1 calc PR A 1
C21 C 0.111(2) 0.1347(7) 0.5886(16) 0.041(4) Uiso 0.788(7) 1 d PD A 1
H21A H 0.0257 0.1356 0.5140 0.050 Uiso 0.788(7) 1 calc PR A 1
C17' C 0.170(7) 0.0986(19) 0.602(4) 0.027(3) Uiso 0.212(7) 1 d PD A 2
H17B H 0.1320 0.0744 0.5332 0.032 Uiso 0.212(7) 1 calc PR A 2
C18' C 0.300(7) 0.088(2) 0.716(6) 0.043(4) Uiso 0.212(7) 1 d PD A 2
H18B H 0.3624 0.0553 0.7334 0.052 Uiso 0.212(7) 1 calc PR A 2
C19' C 0.316(7) 0.132(3) 0.794(4) 0.044(4) Uiso 0.212(7) 1 d PD A 2
H19B H 0.3870 0.1346 0.8753 0.053 Uiso 0.212(7) 1 calc PR A 2
C20' C 0.206(9) 0.173(2) 0.729(6) 0.043(5) Uiso 0.212(7) 1 d PD A 2
H20B H 0.1962 0.2088 0.7582 0.052 Uiso 0.212(7) 1 calc PR A 2
C21' C 0.114(7) 0.150(2) 0.612(5) 0.041(4) Uiso 0.212(7) 1 d PD A 2
H21B H 0.0280 0.1672 0.5529 0.050 Uiso 0.212(7) 1 calc PR A 2
C22 C 0.792(2) 0.2644(4) 0.3480(15) 0.085(6) Uani 1 1 d D . .
H22A H 0.7178 0.2838 0.2758 0.102 Uiso 0.788(7) 1 calc PR A 1
H22B H 0.7379 0.2642 0.2570 0.102 Uiso 0.212(7) 1 calc PR A 2
Cl1 Cl 0.9670(9) 0.2998(3) 0.3968(8) 0.130(3) Uani 1 1 d . A .
Cl2 Cl 0.8390(7) 0.1983(2) 0.3012(7) 0.0833(19) Uani 0.788(7) 1 d PD A 1
Cl3 Cl 0.7076(9) 0.2548(4) 0.4592(7) 0.112(3) Uani 0.788(7) 1 d PD A 1
Cl2' Cl 0.792(3) 0.2014(6) 0.423(2) 0.0833(19) Uani 0.212(7) 1 d PD A 2
Cl3' Cl 0.714(3) 0.3116(8) 0.434(2) 0.112(3) Uani 0.212(7) 1 d PD A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C1 1.881(12) . ?
Ni1 C17 2.098(17) . ?
Ni1 C21' 2.12(7) . ?
Ni1 C20' 2.12(7) . ?
Ni1 C20 2.135(19) . ?
Ni1 C21 2.15(2) . ?
Ni1 C19 2.158(19) . ?
Ni1 C18 2.17(2) . ?
Ni1 C17' 2.18(6) . ?
Ni1 C18' 2.25(6) . ?
Ni1 C19' 2.28(6) . ?
Ni1 I1 2.334(2) . ?
O3 C8 1.183(14) . ?
O4 C9 1.178(14) . ?
N1 C11 1.402(15) . ?
N1 C9 1.429(15) . ?
N1 C8 1.440(15) . ?
N2 C2 1.366(15) . ?
N2 C1 1.370(15) . ?
N2 C13 1.482(15) . ?
N3 C1 1.347(16) . ?
N3 C7 1.398(14) . ?
N3 C15 1.453(15) . ?
C2 C7 1.410(16) . ?
C2 C3 1.415(17) . ?
C3 C4 1.371(17) . ?
C4 C5 1.405(16) . ?
C4 C8 1.477(17) . ?
C5 C6 1.387(16) . ?
C5 C9 1.503(16) . ?
C6 C7 1.377(16) . ?
C10 C12 1.354(17) 3_755 ?
C10 C11 1.402(18) . ?
C11 C12 1.409(18) . ?
C12 C10 1.354(17) 3_755 ?
C13 C14 1.53(2) . ?
C15 C16 1.530(18) . ?
C17 C21 1.36(2) . ?
C17 C18 1.48(2) . ?
C18 C19 1.38(3) . ?
C19 C20 1.43(3) . ?
C20 C21 1.44(2) . ?
C17' C21' 1.36(3) . ?
C17' C18' 1.48(3) . ?
C18' C19' 1.37(3) . ?
C19' C20' 1.43(3) . ?
C20' C21' 1.45(3) . ?
C22 Cl3 1.716(9) . ?
C22 Cl1 1.729(19) . ?
C22 Cl2' 1.757(10) . ?
C22 Cl2 1.788(9) . ?
C22 Cl3' 1.805(9) . ?

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 Ni1 C17 99.6(6) . . ?
C1 Ni1 C21' 131.1(17) . . ?
C17 Ni1 C21' 45.7(15) . . ?
C1 Ni1 C20' 164.8(14) . . ?
C17 Ni1 C20' 65.5(15) . . ?
C21' Ni1 C20' 39.9(13) . . ?
C1 Ni1 C20 158.4(7) . . ?
C17 Ni1 C20 64.9(6) . . ?
C21' Ni1 C20 27.4(15) . . ?
C20' Ni1 C20 16.8(18) . . ?
C1 Ni1 C21 119.4(6) . . ?
C17 Ni1 C21 37.3(6) . . ?
C21' Ni1 C21 12.1(15) . . ?
C20' Ni1 C21 50.3(18) . . ?
C20 Ni1 C21 39.3(7) . . ?
C1 Ni1 C19 150.0(8) . . ?
C17 Ni1 C19 65.5(6) . . ?
C21' Ni1 C19 57.3(16) . . ?
C20' Ni1 C19 22.3(17) . . ?
C20 Ni1 C19 38.9(7) . . ?
C21 Ni1 C19 65.1(7) . . ?
C1 Ni1 C18 114.8(7) . . ?
C17 Ni1 C18 40.5(7) . . ?
C21' Ni1 C18 64.7(16) . . ?
C20' Ni1 C18 52.4(17) . . ?
C20 Ni1 C18 63.9(7) . . ?
C21 Ni1 C18 64.3(7) . . ?
C19 Ni1 C18 37.2(7) . . ?
C1 Ni1 C17' 102.0(13) . . ?
C17 Ni1 C17' 11.6(13) . . ?
C21' Ni1 C17' 37.0(11) . . ?
C20' Ni1 C17' 64.0(16) . . ?
C20 Ni1 C17' 59.7(14) . . ?
C21 Ni1 C17' 27.0(14) . . ?
C19 Ni1 C17' 68.8(14) . . ?
C18 Ni1 C17' 49.8(14) . . ?
C1 Ni1 C18' 103.5(16) . . ?
C17 Ni1 C18' 28.1(16) . . ?
C21' Ni1 C18' 63.2(17) . . ?
C20' Ni1 C18' 62.2(16) . . ?
C20 Ni1 C18' 70.2(15) . . ?
C21 Ni1 C18' 59.4(15) . . ?
C19 Ni1 C18' 50.9(16) . . ?
C18 Ni1 C18' 15.3(13) . . ?
C17' Ni1 C18' 39.0(12) . . ?
C1 Ni1 C19' 132(2) . . ?
C17 Ni1 C19' 56.0(16) . . ?
C21' Ni1 C19' 63.8(17) . . ?
C20' Ni1 C19' 37.8(12) . . ?
C20 Ni1 C19' 52.8(17) . . ?
C21 Ni1 C19' 68.1(15) . . ?
C19 Ni1 C19' 18.1(16) . . ?
C18 Ni1 C19' 20.3(16) . . ?
C17' Ni1 C19' 62.7(16) . . ?
C18' Ni1 C19' 35.3(12) . . ?
C1 Ni1 I1 93.5(4) . . ?
C17 Ni1 I1 165.0(4) . . ?
C21' Ni1 I1 119.5(14) . . ?
C20' Ni1 I1 101.6(14) . . ?
C20 Ni1 I1 100.5(5) . . ?
C21 Ni1 I1 128.7(5) . . ?
C19 Ni1 I1 105.8(5) . . ?
C18 Ni1 I1 137.9(6) . . ?
C17' Ni1 I1 155.6(13) . . ?
C18' Ni1 I1 153.0(17) . . ?
C19' Ni1 I1 118.9(17) . . ?
C11 N1 C9 123.5(10) . . ?
C11 N1 C8 125.2(9) . . ?
C9 N1 C8 111.2(9) . . ?
C2 N2 C1 110.6(9) . . ?
C2 N2 C13 124.9(9) . . ?
C1 N2 C13 124.4(10) . . ?
C1 N3 C7 110.5(9) . . ?
C1 N3 C15 125.1(10) . . ?
C7 N3 C15 124.4(9) . . ?
N3 C1 N2 106.6(10) . . ?
N3 C1 Ni1 128.8(9) . . ?
N2 C1 Ni1 124.6(9) . . ?
N2 C2 C7 106.7(10) . . ?
N2 C2 C3 132.1(11) . . ?
C7 C2 C3 121.2(11) . . ?
C4 C3 C2 114.9(11) . . ?
C3 C4 C5 122.9(11) . . ?
C3 C4 C8 128.6(11) . . ?
C5 C4 C8 108.4(10) . . ?
C6 C5 C4 123.0(10) . . ?
C6 C5 C9 127.8(10) . . ?
C4 C5 C9 109.2(10) . . ?
C7 C6 C5 114.4(10) . . ?
C6 C7 N3 130.9(10) . . ?
C6 C7 C2 123.6(10) . . ?
N3 C7 C2 105.5(9) . . ?
O3 C8 N1 123.7(11) . . ?
O3 C8 C4 130.1(11) . . ?
N1 C8 C4 106.2(9) . . ?
O4 C9 N1 125.1(10) . . ?
O4 C9 C5 130.0(10) . . ?
N1 C9 C5 104.9(10) . . ?
C12 C10 C11 120.4(12) 3_755 . ?
N1 C11 C10 119.8(11) . . ?
N1 C11 C12 120.3(11) . . ?
C10 C11 C12 119.8(11) . . ?
C10 C12 C11 119.8(11) 3_755 . ?
N2 C13 C14 110.0(11) . . ?
N3 C15 C16 110.7(10) . . ?
C21 C17 C18 108.3(14) . . ?
C21 C17 Ni1 73.5(11) . . ?
C18 C17 Ni1 72.4(10) . . ?
C19 C18 C17 107.2(16) . . ?
C19 C18 Ni1 70.9(11) . . ?
C17 C18 Ni1 67.1(10) . . ?
C18 C19 C20 108.3(15) . . ?
C18 C19 Ni1 71.9(11) . . ?
C20 C19 Ni1 69.7(10) . . ?
C19 C20 C21 107.6(15) . . ?
C19 C20 Ni1 71.4(11) . . ?
C21 C20 Ni1 70.9(11) . . ?
C17 C21 C20 108.2(15) . . ?
C17 C21 Ni1 69.2(11) . . ?
C20 C21 Ni1 69.7(11) . . ?
C21' C17' C18' 107(2) . . ?
C21' C17' Ni1 69(4) . . ?
C18' C17' Ni1 73(3) . . ?
C19' C18' C17' 109(2) . . ?
C19' C18' Ni1 74(4) . . ?
C17' C18' Ni1 68(3) . . ?
C18' C19' C20' 107(2) . . ?
C18' C19' Ni1 71(3) . . ?
C20' C19' Ni1 65(3) . . ?
C19' C20' C21' 108(2) . . ?
C19' C20' Ni1 77(3) . . ?
C21' C20' Ni1 70(4) . . ?
C17' C21' C20' 108(2) . . ?
C17' C21' Ni1 74(4) . . ?
C20' C21' Ni1 70(4) . . ?
Cl3 C22 Cl1 114.6(10) . . ?
Cl3 C22 Cl2' 55.9(8) . . ?
Cl1 C22 Cl2' 115.1(14) . . ?
Cl3 C22 Cl2 108.2(7) . . ?
Cl1 C22 Cl2 105.1(8) . . ?
Cl2' C22 Cl2 53.6(9) . . ?
Cl3 C22 Cl3' 47.4(8) . . ?
Cl1 C22 Cl3' 89.5(11) . . ?
Cl2' C22 Cl3' 102.6(7) . . ?
Cl2 C22 Cl3' 155.6(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.986
_refine_diff_density_min         -2.686
_refine_diff_density_rms         0.331
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform '
_database_code_depnum_ccdc_archive 'CCDC 1020161'
#######################################################################
#
#                 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_ic16325

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '[5]I'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 I N3 O2'
_chemical_formula_weight         447.26

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'
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   P2(1)/c

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

_cell_length_a                   14.4332(10)
_cell_length_b                   8.5362(6)
_cell_length_c                   15.4137(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.356(2)
_cell_angle_gamma                90.00
_cell_volume                     1868.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4801
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.32

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    1.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6715
_exptl_absorpt_correction_T_max  0.8063
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_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            13991
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4273
_reflns_number_gt                3781
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.2929P] 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         4273
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.216
_refine_ls_shift/su_max          0.003
_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 0.554862(17) 1.31374(3) 1.177630(15) 0.02909(10) Uani 1 1 d . . .
O1 O 0.16270(18) 0.4254(3) 0.86239(19) 0.0355(6) Uani 1 1 d . . .
O2 O -0.0350(2) 0.8130(3) 0.9249(2) 0.0448(8) Uani 1 1 d . . .
N1 N 0.4100(2) 0.8337(3) 1.07732(19) 0.0230(6) Uani 1 1 d . . .
N2 N 0.3147(2) 1.0165(3) 1.10739(18) 0.0226(6) Uani 1 1 d . . .
N3 N 0.0439(2) 0.5992(3) 0.8802(2) 0.0274(7) Uani 1 1 d . . .
C1 C 0.4036(2) 0.9663(4) 1.1207(2) 0.0233(7) Uani 1 1 d . . .
H1 H 0.4551 1.0182 1.1563 0.028 Uiso 1 1 calc R . .
C2 C 0.3207(3) 0.7904(4) 1.0355(2) 0.0221(7) Uani 1 1 d . . .
C3 C 0.2890(2) 0.6597(4) 0.9843(2) 0.0218(7) Uani 1 1 d . . .
H3 H 0.3298 0.5783 0.9722 0.026 Uiso 1 1 calc R . .
C4 C 0.1937(3) 0.6593(4) 0.9528(2) 0.0239(7) Uani 1 1 d . . .
C5 C 0.1332(2) 0.7790(4) 0.9701(2) 0.0239(7) Uani 1 1 d . . .
C6 C 0.1633(2) 0.9086(4) 1.0209(2) 0.0256(7) Uani 1 1 d . . .
H6 H 0.1220 0.9897 1.0323 0.031 Uiso 1 1 calc R . .
C7 C 0.2596(2) 0.9096(4) 1.0540(2) 0.0227(7) Uani 1 1 d . . .
C8 C 0.1370(3) 0.5426(4) 0.8942(2) 0.0268(7) Uani 1 1 d . . .
C9 C 0.0370(3) 0.7405(5) 0.9248(2) 0.0320(8) Uani 1 1 d . . .
C10 C -0.0352(3) 0.5262(5) 0.8259(2) 0.0299(8) Uani 1 1 d . . .
C11 C -0.0569(3) 0.3728(5) 0.8406(3) 0.0381(10) Uani 1 1 d . . .
H11 H -0.0183 0.3130 0.8850 0.046 Uiso 1 1 calc R . .
C12 C -0.1365(4) 0.3066(5) 0.7891(3) 0.0484(13) Uani 1 1 d . . .
H12 H -0.1517 0.2000 0.7974 0.058 Uiso 1 1 calc R . .
C13 C -0.1934(3) 0.3953(7) 0.7261(3) 0.0500(12) Uani 1 1 d . . .
H13 H -0.2486 0.3502 0.6924 0.060 Uiso 1 1 calc R . .
C14 C -0.1708(3) 0.5489(6) 0.7117(3) 0.0450(11) Uani 1 1 d . . .
H14 H -0.2097 0.6091 0.6677 0.054 Uiso 1 1 calc R . .
C15 C -0.0912(3) 0.6147(5) 0.7616(3) 0.0370(9) Uani 1 1 d . . .
H15 H -0.0749 0.7203 0.7518 0.044 Uiso 1 1 calc R . .
C16 C 0.4945(3) 0.7328(4) 1.0833(2) 0.0281(8) Uani 1 1 d . . .
H16A H 0.4942 0.6822 1.0255 0.034 Uiso 1 1 calc R . .
H16B H 0.4917 0.6491 1.1272 0.034 Uiso 1 1 calc R . .
C17 C 0.5852(3) 0.8233(5) 1.1094(3) 0.0364(9) Uani 1 1 d . . .
H17A H 0.5856 0.9124 1.0695 0.055 Uiso 1 1 calc R . .
H17B H 0.6387 0.7546 1.1058 0.055 Uiso 1 1 calc R . .
H17C H 0.5899 0.8614 1.1700 0.055 Uiso 1 1 calc R . .
C18 C 0.2811(3) 1.1586(4) 1.1474(3) 0.0292(8) Uani 1 1 d . . .
H18A H 0.3276 1.1889 1.2000 0.035 Uiso 1 1 calc R . .
H18B H 0.2208 1.1352 1.1668 0.035 Uiso 1 1 calc R . .
C19 C 0.2671(3) 1.2935(4) 1.0828(3) 0.0387(10) Uani 1 1 d . . .
H19A H 0.3269 1.3178 1.0642 0.058 Uiso 1 1 calc R . .
H19B H 0.2451 1.3856 1.1112 0.058 Uiso 1 1 calc R . .
H19C H 0.2201 1.2644 1.0312 0.058 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 C8 1.201(4) . ?
O2 C9 1.210(5) . ?
N1 C1 1.326(4) . ?
N1 C2 1.384(5) . ?
N1 C16 1.482(5) . ?
N2 C1 1.334(4) . ?
N2 C7 1.381(4) . ?
N2 C18 1.480(4) . ?
N3 C9 1.400(5) . ?
N3 C8 1.407(5) . ?
N3 C10 1.432(4) . ?
C2 C3 1.395(5) . ?
C2 C7 1.408(5) . ?
C3 C4 1.375(5) . ?
C4 C5 1.399(5) . ?
C4 C8 1.487(5) . ?
C5 C6 1.380(5) . ?
C5 C9 1.475(5) . ?
C6 C7 1.393(5) . ?
C10 C11 1.375(6) . ?
C10 C15 1.386(6) . ?
C11 C12 1.393(6) . ?
C12 C13 1.380(7) . ?
C13 C14 1.379(7) . ?
C14 C15 1.381(6) . ?
C16 C17 1.510(5) . ?
C18 C19 1.511(5) . ?

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 N1 C2 108.6(3) . . ?
C1 N1 C16 126.6(3) . . ?
C2 N1 C16 124.1(3) . . ?
C1 N2 C7 108.3(3) . . ?
C1 N2 C18 125.2(3) . . ?
C7 N2 C18 126.4(3) . . ?
C9 N3 C8 111.8(3) . . ?
C9 N3 C10 122.8(3) . . ?
C8 N3 C10 125.4(3) . . ?
N1 C1 N2 110.4(3) . . ?
N1 C2 C3 131.3(3) . . ?
N1 C2 C7 106.1(3) . . ?
C3 C2 C7 122.6(3) . . ?
C4 C3 C2 114.0(3) . . ?
C3 C4 C5 123.3(3) . . ?
C3 C4 C8 128.5(3) . . ?
C5 C4 C8 108.1(3) . . ?
C6 C5 C4 123.4(3) . . ?
C6 C5 C9 128.3(3) . . ?
C4 C5 C9 108.3(3) . . ?
C5 C6 C7 113.8(3) . . ?
N2 C7 C6 130.7(3) . . ?
N2 C7 C2 106.5(3) . . ?
C6 C7 C2 122.8(3) . . ?
O1 C8 N3 125.4(3) . . ?
O1 C8 C4 129.0(3) . . ?
N3 C8 C4 105.6(3) . . ?
O2 C9 N3 125.3(3) . . ?
O2 C9 C5 128.4(4) . . ?
N3 C9 C5 106.3(3) . . ?
C11 C10 C15 121.1(4) . . ?
C11 C10 N3 120.0(4) . . ?
C15 C10 N3 118.8(4) . . ?
C10 C11 C12 118.8(4) . . ?
C13 C12 C11 120.3(4) . . ?
C14 C13 C12 120.4(4) . . ?
C13 C14 C15 119.7(4) . . ?
C14 C15 C10 119.7(4) . . ?
N1 C16 C17 112.5(3) . . ?
N2 C18 C19 111.4(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.229
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.119
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile, ether'
_database_code_depnum_ccdc_archive 'CCDC 1020162'
