#######################################################################
#
#                 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_ff06pc1n
_database_code_depnum_ccdc_archive 'CCDC 651791'

_audit_creation_date             2006-11-08T10:34:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C13 H15 I1 N4 O1'
_chemical_formula_sum            'C13 H15 I N4 O'
_chemical_formula_weight         370.19
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   7.4415(13)
_cell_length_b                   21.445(4)
_cell_length_c                   8.9163(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.154(2)
_cell_angle_gamma                90
_cell_volume                     1379.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4722
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      26.4
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.319
_exptl_absorpt_correction_T_min  0.4959
_exptl_absorpt_correction_T_max  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_number            11541
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.9
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2713
_reflns_number_gt                2139
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       "'BRUKER Smart"
_computing_cell_refinement       "'BRUKER Smart"
_computing_data_reduction        'APPEX2 (BRUKER AXS, 2005)'
_computing_structure_solution    'DIRDIF99 (Beurskens et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0336P)^2^+0.2723P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         2713
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.105

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.03206(3) 0.226962(10) 0.00036(2) 0.02103(9) Uani 1 1 d . . .
C1 C 0.2765(5) 0.28434(14) 0.0280(4) 0.0177(7) Uani 1 1 d . . .
H1 H 0.3544 0.2788 0.133 0.021 Uiso 1 1 calc R . .
C2 C 0.3892(4) 0.26880(14) -0.0875(4) 0.0159(7) Uani 1 1 d . . .
H2 H 0.3076 0.2687 -0.192 0.019 Uiso 1 1 calc R . .
C3 C 0.5221(5) 0.32474(15) -0.0705(4) 0.0228(7) Uani 1 1 d . . .
H3A H 0.558 0.3323 -0.1665 0.027 Uiso 1 1 calc R . .
H3B H 0.6329 0.3173 0.011 0.027 Uiso 1 1 calc R . .
C5 C 0.2322(5) 0.35330(15) 0.0005(4) 0.0221(8) Uani 1 1 d . . .
H5A H 0.2033 0.3723 0.0904 0.027 Uiso 1 1 calc R . .
H5B H 0.1284 0.3593 -0.0883 0.027 Uiso 1 1 calc R . .
C4 C 0.4119(5) 0.38090(16) -0.0295(4) 0.0242(8) Uani 1 1 d . B .
H4 H 0.3794 0.4089 -0.1189 0.029 Uiso 1 1 calc R . .
N6 N 0.4839(4) 0.20880(12) -0.0581(3) 0.0153(6) Uani 1 1 d . . .
N7 N 0.5960(4) 0.19624(13) 0.0830(3) 0.0227(6) Uani 1 1 d . . .
N8 N 0.6596(4) 0.13941(13) 0.0784(3) 0.0217(6) Uani 1 1 d . . .
C9 C 0.5888(4) 0.11528(15) -0.0656(4) 0.0178(7) Uani 1 1 d . . .
C10 C 0.4773(5) 0.15969(15) -0.1518(4) 0.0168(7) Uani 1 1 d . . .
C11 C 0.6301(4) 0.05174(15) -0.1073(4) 0.0191(7) Uani 1 1 d . . .
C12 C 0.7514(5) 0.01376(16) -0.0046(4) 0.0231(8) Uani 1 1 d . . .
H12 H 0.81 0.0281 0.0936 0.028 Uiso 1 1 calc R . .
C13 C 0.7843(5) -0.04562(17) -0.0500(4) 0.0256(8) Uani 1 1 d . . .
H13 H 0.867 -0.0717 0.0165 0.031 Uiso 1 1 calc R . .
C14 C 0.6937(5) -0.06582(16) -0.1944(4) 0.0279(8) Uani 1 1 d . . .
H14 H 0.7116 -0.106 -0.2272 0.033 Uiso 1 1 calc R . .
C15 C 0.5761(6) -0.02536(18) -0.2894(5) 0.0381(10) Uani 1 1 d . . .
H15 H 0.5178 -0.0389 -0.3884 0.046 Uiso 1 1 calc R . .
N16 N 0.5398(5) 0.03249(14) -0.2483(4) 0.0355(8) Uani 1 1 d . . .
C41 C 0.5266(5) 0.41614(18) 0.1057(5) 0.0322(9) Uani 1 1 d . . .
H41A H 0.454 0.449 0.1372 0.039 Uiso 0.5 1 calc PR A 1
H41B H 0.5714 0.3884 0.1928 0.039 Uiso 0.5 1 calc PR A 1
H41C H 0.5509 0.3833 0.1955 0.039 Uiso 0.5 1 d PR A 2
H41D H 0.6462 0.4336 0.0814 0.039 Uiso 0.5 1 d PR A 2
O42 O 0.6840(7) 0.4429(2) 0.0521(6) 0.0306(12) Uani 0.5 1 d P B 1
H42 H 0.7801 0.4383 0.1195 0.037 Uiso 0.5 1 calc PR B 1
O42B O 0.4328(7) 0.4625(2) 0.1699(6) 0.0337(13) Uani 0.5 1 d P B 2
H42B H 0.4006 0.4907 0.107 0.04 Uiso 0.5 1 calc PR B 2
H10 H 0.406(4) 0.1597(14) -0.247(4) 0.012(8) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01638(13) 0.02452(13) 0.02418(14) 0.00018(10) 0.00878(9) -0.00205(10)
C1 0.0146(17) 0.0237(19) 0.0144(17) -0.0053(13) 0.0028(13) -0.0030(13)
C2 0.0121(16) 0.0185(17) 0.0168(17) -0.0008(13) 0.0030(13) -0.0023(13)
C3 0.0212(19) 0.0224(18) 0.0274(19) -0.0040(16) 0.0113(15) -0.0051(15)
C5 0.0216(19) 0.0240(18) 0.0222(19) -0.0052(14) 0.0079(15) -0.0020(14)
C4 0.025(2) 0.0231(19) 0.024(2) -0.0023(14) 0.0061(15) -0.0023(15)
N6 0.0109(14) 0.0218(14) 0.0123(13) 0.0000(11) 0.0011(10) 0.0015(10)
N7 0.0211(16) 0.0281(17) 0.0164(15) -0.0007(12) -0.0001(12) 0.0042(13)
N8 0.0184(15) 0.0256(16) 0.0184(16) 0.0008(12) -0.0011(12) 0.0019(12)
C9 0.0126(17) 0.0213(18) 0.0188(18) 0.0008(13) 0.0028(14) -0.0035(13)
C10 0.0149(17) 0.0207(18) 0.0143(17) -0.0009(13) 0.0026(14) -0.0020(13)
C11 0.0183(18) 0.0176(17) 0.0218(19) 0.0023(14) 0.0056(14) -0.0019(13)
C12 0.0178(19) 0.027(2) 0.0235(19) 0.0038(14) 0.0042(15) -0.0003(14)
C13 0.0182(18) 0.028(2) 0.031(2) 0.0085(16) 0.0061(15) 0.0050(15)
C14 0.027(2) 0.0207(19) 0.039(2) 0.0030(16) 0.0121(17) -0.0007(15)
C15 0.055(3) 0.0217(19) 0.029(2) -0.0055(17) -0.0054(19) 0.0018(18)
N16 0.050(2) 0.0199(17) 0.0272(18) -0.0023(14) -0.0093(15) 0.0059(14)
C41 0.024(2) 0.034(2) 0.039(2) -0.0116(17) 0.0072(17) -0.0054(16)
O42 0.023(3) 0.036(3) 0.027(3) 0.002(2) -0.004(2) -0.015(2)
O42B 0.036(3) 0.026(3) 0.038(3) -0.007(2) 0.007(3) 0.002(2)


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C1 2.160(3) . ?
C1 C2 1.516(4) . ?
C1 C5 1.522(4) . ?
C1 H1 0.98 . ?
C2 N6 1.459(4) . ?
C2 C3 1.538(4) . ?
C2 H2 0.98 . ?
C3 C4 1.550(5) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C5 C4 1.544(5) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C4 C41 1.500(5) . ?
C4 H4 0.98 . ?
N6 C10 1.338(4) . ?
N6 N7 1.355(4) . ?
N7 N8 1.311(4) . ?
N8 C9 1.365(4) . ?
C9 C10 1.369(4) . ?
C9 C11 1.465(4) . ?
C10 H10 0.88(3) . ?
C11 N16 1.338(4) . ?
C11 C12 1.383(5) . ?
C12 C13 1.376(5) . ?
C12 H12 0.93 . ?
C13 C14 1.370(5) . ?
C13 H13 0.93 . ?
C14 C15 1.368(5) . ?
C14 H14 0.93 . ?
C15 N16 1.339(5) . ?
C15 H15 0.93 . ?
C41 O42B 1.413(6) . ?
C41 O42 1.485(6) . ?
C41 H41A 0.97 . ?
C41 H41B 0.97 . ?
C41 H41C 1.0487 . ?
C41 H41D 1.0368 . ?
O42 H41D 0.4721 . ?
O42 H42 0.82 . ?
O42B H42B 0.82 . ?

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
C2 C1 C5 103.8(3) . . ?
C2 C1 I1 112.8(2) . . ?
C5 C1 I1 113.1(2) . . ?
C2 C1 H1 109 . . ?
C5 C1 H1 109 . . ?
I1 C1 H1 109 . . ?
N6 C2 C1 113.2(3) . . ?
N6 C2 C3 113.5(3) . . ?
C1 C2 C3 102.2(2) . . ?
N6 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C2 C3 C4 105.3(3) . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C1 C5 C4 103.8(3) . . ?
C1 C5 H5A 111 . . ?
C4 C5 H5A 111 . . ?
C1 C5 H5B 111 . . ?
C4 C5 H5B 111 . . ?
H5A C5 H5B 109 . . ?
C41 C4 C5 113.6(3) . . ?
C41 C4 C3 110.6(3) . . ?
C5 C4 C3 105.9(3) . . ?
C41 C4 H4 108.9 . . ?
C5 C4 H4 108.9 . . ?
C3 C4 H4 108.9 . . ?
C10 N6 N7 110.1(3) . . ?
C10 N6 C2 129.7(3) . . ?
N7 N6 C2 120.2(3) . . ?
N8 N7 N6 107.5(3) . . ?
N7 N8 C9 108.8(3) . . ?
N8 C9 C10 107.8(3) . . ?
N8 C9 C11 122.3(3) . . ?
C10 C9 C11 129.8(3) . . ?
N6 C10 C9 105.8(3) . . ?
N6 C10 H10 121(2) . . ?
C9 C10 H10 133(2) . . ?
N16 C11 C12 122.5(3) . . ?
N16 C11 C9 115.9(3) . . ?
C12 C11 C9 121.6(3) . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 118.3(3) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
N16 C15 C14 124.0(4) . . ?
N16 C15 H15 118 . . ?
C14 C15 H15 118 . . ?
C11 N16 C15 117.0(3) . . ?
O42B C41 O42 111.4(4) . . ?
O42B C41 C4 116.1(4) . . ?
O42 C41 C4 105.9(3) . . ?
O42 C41 H41A 110.6 . . ?
C4 C41 H41A 110.6 . . ?
O42B C41 H41B 102.4 . . ?
O42 C41 H41B 110.6 . . ?
C4 C41 H41B 110.6 . . ?
H41A C41 H41B 108.7 . . ?
O42B C41 H41C 100 . . ?
O42 C41 H41C 120.2 . . ?
C4 C41 H41C 103.5 . . ?
H41A C41 H41C 105.8 . . ?
O42B C41 H41D 111.4 . . ?
C4 C41 H41D 111.3 . . ?
H41A C41 H41D 111.4 . . ?
H41B C41 H41D 104.2 . . ?
H41C C41 H41D 114 . . ?
C41 O42 H42 109.5 . . ?
H41D O42 H42 94.2 . . ?
C41 O42B H42B 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
C5 C1 C2 N6 166.4(3) . . . . ?
I1 C1 C2 N6 -70.8(3) . . . . ?
C5 C1 C2 C3 44.0(3) . . . . ?
I1 C1 C2 C3 166.7(2) . . . . ?
N6 C2 C3 C4 -154.3(3) . . . . ?
C1 C2 C3 C4 -32.0(3) . . . . ?
C2 C1 C5 C4 -38.7(3) . . . . ?
I1 C1 C5 C4 -161.3(2) . . . . ?
C1 C5 C4 C41 -103.4(3) . . . . ?
C1 C5 C4 C3 18.1(3) . . . . ?
C2 C3 C4 C41 132.0(3) . . . . ?
C2 C3 C4 C5 8.6(4) . . . . ?
C1 C2 N6 C10 124.8(3) . . . . ?
C3 C2 N6 C10 -119.2(4) . . . . ?
C1 C2 N6 N7 -54.0(4) . . . . ?
C3 C2 N6 N7 62.0(4) . . . . ?
C10 N6 N7 N8 -0.2(4) . . . . ?
C2 N6 N7 N8 178.8(3) . . . . ?
N6 N7 N8 C9 0.1(4) . . . . ?
N7 N8 C9 C10 0.0(4) . . . . ?
N7 N8 C9 C11 -178.6(3) . . . . ?
N7 N6 C10 C9 0.2(4) . . . . ?
C2 N6 C10 C9 -178.7(3) . . . . ?
N8 C9 C10 N6 -0.1(4) . . . . ?
C11 C9 C10 N6 178.4(3) . . . . ?
N8 C9 C11 N16 174.9(3) . . . . ?
C10 C9 C11 N16 -3.4(5) . . . . ?
N8 C9 C11 C12 -3.4(5) . . . . ?
C10 C9 C11 C12 178.3(3) . . . . ?
N16 C11 C12 C13 1.5(5) . . . . ?
C9 C11 C12 C13 179.7(3) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C12 C13 C14 C15 1.3(5) . . . . ?
C13 C14 C15 N16 -1.9(6) . . . . ?
C12 C11 N16 C15 -2.0(5) . . . . ?
C9 C11 N16 C15 179.7(3) . . . . ?
C14 C15 N16 C11 2.3(6) . . . . ?
C5 C4 C41 O42B -51.6(5) . . . . ?
C3 C4 C41 O42B -170.5(4) . . . . ?
C5 C4 C41 O42 -175.9(3) . . . . ?
C3 C4 C41 O42 65.3(4) . . . . ?