# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZX_I2
_database_code_depnum_ccdc_archive 'CCDC 1475009'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                              CHEMICAL_INFORMATION                          #
#----------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H5 I2 N O2'
_chemical_formula_sum            'C12 H5 I2 N O2'
_chemical_formula_weight         448.97
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      Monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.3887(3)
_cell_length_b                   23.7759(18)
_cell_length_c                   11.1283(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.847(3)
_cell_angle_gamma                90
_cell_volume                     1159.75(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9818
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.50
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.571
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    5.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.417
_exptl_absorpt_correction_T_max  0.685

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0302
_diffrn_reflns_av_uneti/neti     0.0246
_diffrn_reflns_number            11189
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.157
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2656
_reflns_number_gt                2463
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CRYSCALc (T. Roisnel, local program, 2015)'

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

_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     
'w=1/[σ²(Fo²)+(0.0145P)²+2.1997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2656
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0501
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_restrained_S_all      1.217
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.578
_refine_diff_density_min         -1.089
_refine_diff_density_rms         0.139

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ...........................................................
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                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 0.0000 0.0000 '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 0.0060 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5463(7) 0.48149(13) 0.7468(3) 0.0131(6) Uani 1 1 d . . . . .
C2 C 0.3620(7) 0.49367(14) 0.8411(3) 0.0159(6) Uani 1 1 d . . . . .
H2 H 0.3144 0.5317 0.8587 0.019 Uiso 1 1 calc R U . . .
C3 C 0.2457(8) 0.45019(15) 0.9105(3) 0.0192(7) Uani 1 1 d . . . . .
H3 H 0.1236 0.4590 0.9761 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3069(8) 0.39476(14) 0.8843(3) 0.0156(7) Uani 1 1 d . . . . .
H4 H 0.2246 0.3655 0.9310 0.019 Uiso 1 1 calc R U . . .
C5 C 0.4907(7) 0.38162(13) 0.7889(3) 0.0120(6) Uani 1 1 d . . . . .
C6 C 0.6108(7) 0.42513(13) 0.7221(3) 0.0114(6) Uani 1 1 d . . . . .
O7 O 0.7998(5) 0.41480(9) 0.6302(2) 0.0131(4) Uani 1 1 d . . . . .
C8 C 0.8684(7) 0.36086(13) 0.5998(3) 0.0116(6) Uani 1 1 d . . . . .
C9 C 0.7513(7) 0.31382(13) 0.6585(3) 0.0103(6) Uani 1 1 d . . . . .
C10 C 0.5547(7) 0.32231(14) 0.7604(3) 0.0137(6) Uani 1 1 d . . . . .
O11 O 0.4492(6) 0.28396(10) 0.8181(2) 0.0254(6) Uani 1 1 d . . . . .
C12 C 0.8374(7) 0.26115(13) 0.6125(3) 0.0123(6) Uani 1 1 d . . . . .
C13 C 1.0278(8) 0.25888(14) 0.5173(3) 0.0157(6) Uani 1 1 d . . . . .
H13 H 1.0865 0.2237 0.4850 0.019 Uiso 1 1 calc R U . . .
C14 C 1.1316(8) 0.30892(14) 0.4696(3) 0.0171(7) Uani 1 1 d . . . . .
H14 H 1.2646 0.3069 0.4049 0.020 Uiso 1 1 calc R U . . .
N15 N 1.0550(6) 0.35961(11) 0.5095(2) 0.0143(5) Uani 1 1 d . . . . .
I1 I 0.72057(5) 0.54592(2) 0.64148(2) 0.01465(7) Uani 1 1 d . . . . .
I2 I 0.69559(5) 0.18304(2) 0.67815(2) 0.01670(7) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                               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
C1 C2 1.387(5) . ?
C1 C6 1.399(4) . ?
C1 I1 2.096(3) . ?
C2 C3 1.402(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 C10 1.475(4) . ?
C6 O7 1.371(4) . ?
O7 C8 1.364(4) . ?
C8 N15 1.328(4) . ?
C8 C9 1.405(4) . ?
C9 C12 1.411(4) . ?
C9 C10 1.473(4) . ?
C10 O11 1.220(4) . ?
C12 C13 1.383(5) . ?
C12 I2 2.101(3) . ?
C13 C14 1.389(5) . ?
C13 H13 0.9500 . ?
C14 N15 1.333(4) . ?
C14 H14 0.9500 . ?

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 C6 118.7(3) . . ?
C2 C1 I1 120.9(2) . . ?
C6 C1 I1 120.5(2) . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 C10 121.0(3) . . ?
C4 C5 C10 119.9(3) . . ?
O7 C6 C5 121.6(3) . . ?
O7 C6 C1 117.0(3) . . ?
C5 C6 C1 121.4(3) . . ?
C8 O7 C6 120.2(2) . . ?
N15 C8 O7 111.2(3) . . ?
N15 C8 C9 126.0(3) . . ?
O7 C8 C9 122.9(3) . . ?
C8 C9 C12 115.3(3) . . ?
C8 C9 C10 119.4(3) . . ?
C12 C9 C10 125.3(3) . . ?
O11 C10 C9 123.7(3) . . ?
O11 C10 C5 121.4(3) . . ?
C9 C10 C5 114.9(3) . . ?
C13 C12 C9 119.7(3) . . ?
C13 C12 I2 115.6(2) . . ?
C9 C12 I2 124.7(2) . . ?
C12 C13 C14 118.8(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
N15 C14 C13 123.6(3) . . ?
N15 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
C8 N15 C14 116.6(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
C6 C1 C2 C3 0.5(5) . . . . ?
I1 C1 C2 C3 179.7(3) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C3 C4 C5 C10 -179.6(3) . . . . ?
C4 C5 C6 O7 177.9(3) . . . . ?
C10 C5 C6 O7 -2.0(5) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C10 C5 C6 C1 178.6(3) . . . . ?
C2 C1 C6 O7 -178.4(3) . . . . ?
I1 C1 C6 O7 2.4(4) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
I1 C1 C6 C5 -178.2(2) . . . . ?
C5 C6 O7 C8 1.7(4) . . . . ?
C1 C6 O7 C8 -178.9(3) . . . . ?
C6 O7 C8 N15 -179.7(3) . . . . ?
C6 O7 C8 C9 0.5(4) . . . . ?
N15 C8 C9 C12 -2.0(5) . . . . ?
O7 C8 C9 C12 177.8(3) . . . . ?
N15 C8 C9 C10 177.8(3) . . . . ?
O7 C8 C9 C10 -2.4(5) . . . . ?
C8 C9 C10 O11 -178.3(3) . . . . ?
C12 C9 C10 O11 1.5(5) . . . . ?
C8 C9 C10 C5 2.0(4) . . . . ?
C12 C9 C10 C5 -178.2(3) . . . . ?
C6 C5 C10 O11 -179.7(3) . . . . ?
C4 C5 C10 O11 0.4(5) . . . . ?
C6 C5 C10 C9 0.1(4) . . . . ?
C4 C5 C10 C9 -179.8(3) . . . . ?
C8 C9 C12 C13 0.8(4) . . . . ?
C10 C9 C12 C13 -179.0(3) . . . . ?
C8 C9 C12 I2 -179.0(2) . . . . ?
C10 C9 C12 I2 1.2(5) . . . . ?
C9 C12 C13 C14 0.5(5) . . . . ?
I2 C12 C13 C14 -179.7(2) . . . . ?
C12 C13 C14 N15 -0.9(5) . . . . ?
O7 C8 N15 C14 -178.2(3) . . . . ?
C9 C8 N15 C14 1.6(5) . . . . ?
C13 C14 N15 C8 -0.1(5) . . . . ?

#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR AZX_I2                                               #
#----------------------------------------------------------------------------#
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_HM110
_database_code_depnum_ccdc_archive 'CCDC 1475010'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_date             2015-03-09T19:03:08-00:00
_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         'C26 H16 O2'
_chemical_formula_sum            'C26 H16 O2'
_chemical_formula_weight         360.39
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   8.1791(3)
_cell_length_b                   15.1330(9)
_cell_length_c                   14.8514(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.614(2)
_cell_angle_gamma                90
_cell_volume                     1806.77(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2668
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      24.54
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.986


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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_number            16086
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4140
_reflns_number_gt                2969
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare 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, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;

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

_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)+(0.0609P)²+0.3171P] 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_number_reflns         4140
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.79
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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'
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
C1 C 0.6242(2) 0.77085(11) 0.54091(11) 0.0237(4) Uani 1 1 d . . .
C2 C 0.5703(2) 0.84322(11) 0.47071(12) 0.0254(4) Uani 1 1 d . . .
C3 C 0.6579(2) 0.87717(12) 0.40687(12) 0.0301(4) Uani 1 1 d . . .
H3 H 0.764 0.8543 0.4019 0.036 Uiso 1 1 calc R . .
C4 C 0.5868(3) 0.94535(12) 0.35052(13) 0.0345(5) Uani 1 1 d . . .
H4 H 0.6454 0.9698 0.3068 0.041 Uiso 1 1 calc R . .
C5 C 0.4318(3) 0.97827(12) 0.35716(13) 0.0358(5) Uani 1 1 d . . .
H5 H 0.3851 1.0248 0.3177 0.043 Uiso 1 1 calc R . .
C6 C 0.3434(2) 0.94436(12) 0.42057(13) 0.0324(4) Uani 1 1 d . . .
H6 H 0.2366 0.9669 0.4247 0.039 Uiso 1 1 calc R . .
C7 C 0.4143(2) 0.87676(11) 0.47789(12) 0.0256(4) Uani 1 1 d . . .
C8 C 0.3573(2) 0.83142(12) 0.55445(12) 0.0271(4) Uani 1 1 d . . .
C9 C 0.2126(2) 0.84091(13) 0.59042(13) 0.0343(5) Uani 1 1 d . . .
H9 H 0.128 0.881 0.5638 0.041 Uiso 1 1 calc R . .
C10 C 0.1946(3) 0.79050(13) 0.66602(14) 0.0375(5) Uani 1 1 d . . .
H10 H 0.0967 0.7965 0.6914 0.045 Uiso 1 1 calc R . .
C11 C 0.3169(2) 0.73161(13) 0.70524(13) 0.0364(5) Uani 1 1 d . . .
H11 H 0.3014 0.6974 0.7567 0.044 Uiso 1 1 calc R . .
C12 C 0.4619(2) 0.72207(12) 0.67005(12) 0.0314(4) Uani 1 1 d . . .
H12 H 0.5465 0.6823 0.6974 0.038 Uiso 1 1 calc R . .
C13 C 0.4805(2) 0.77173(11) 0.59440(11) 0.0250(4) Uani 1 1 d . . .
C14 C 0.6301(2) 0.67960(11) 0.49628(11) 0.0220(4) Uani 1 1 d . . .
C15 C 0.5297(2) 0.66445(11) 0.41071(11) 0.0248(4) Uani 1 1 d . . .
H15 H 0.4616 0.7112 0.3823 0.03 Uiso 1 1 calc R . .
C16 C 0.5256(2) 0.58410(12) 0.36588(12) 0.0285(4) Uani 1 1 d . . .
H16 H 0.4552 0.5771 0.3079 0.034 Uiso 1 1 calc R . .
C17 C 0.6224(2) 0.51364(12) 0.40421(12) 0.0272(4) Uani 1 1 d . . .
H17 H 0.621 0.4588 0.373 0.033 Uiso 1 1 calc R . .
C18 C 0.7208(2) 0.52590(11) 0.48916(12) 0.0250(4) Uani 1 1 d . . .
C19 C 0.7250(2) 0.60767(11) 0.53596(11) 0.0235(4) Uani 1 1 d . . .
C20 C 0.8380(2) 0.59538(12) 0.62680(12) 0.0280(4) Uani 1 1 d . . .
C21 C 0.9029(2) 0.50341(12) 0.62783(13) 0.0303(4) Uani 1 1 d . . .
C22 C 1.0153(2) 0.46060(14) 0.69481(15) 0.0404(5) Uani 1 1 d . . .
H22 H 1.0619 0.4891 0.7507 0.048 Uiso 1 1 calc R . .
C23 C 1.0573(3) 0.37370(15) 0.67670(17) 0.0460(6) Uani 1 1 d . . .
H23 H 1.1356 0.3426 0.7206 0.055 Uiso 1 1 calc R . .
C24 C 0.9867(3) 0.33229(14) 0.59603(17) 0.0453(6) Uani 1 1 d . . .
H24 H 1.016 0.2728 0.5859 0.054 Uiso 1 1 calc R . .
C25 C 0.8734(2) 0.37595(13) 0.52908(14) 0.0355(5) Uani 1 1 d . . .
H25 H 0.8254 0.3471 0.4737 0.043 Uiso 1 1 calc R . .
C26 C 0.8330(2) 0.46236(12) 0.54560(13) 0.0287(4) Uani 1 1 d . . .
O1 O 0.77991(15) 0.79649(9) 0.59369(9) 0.0326(3) Uani 1 1 d . . .
H1 H 0.814(3) 0.7521(15) 0.6376(16) 0.049 Uiso 1 1 d . . .
O2 O 0.87056(16) 0.64864(9) 0.69023(9) 0.0388(4) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   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
C1 O1 1.421(2) . ?
C1 C2 1.520(2) . ?
C1 C13 1.535(2) . ?
C1 C14 1.536(2) . ?
C2 C3 1.388(2) . ?
C2 C7 1.396(2) . ?
C3 C4 1.387(3) . ?
C3 H3 0.95 . ?
C4 C5 1.383(3) . ?
C4 H4 0.95 . ?
C5 C6 1.387(3) . ?
C5 H5 0.95 . ?
C6 C7 1.388(3) . ?
C6 H6 0.95 . ?
C7 C8 1.475(2) . ?
C8 C9 1.393(3) . ?
C8 C13 1.401(2) . ?
C9 C10 1.387(3) . ?
C9 H9 0.95 . ?
C10 C11 1.385(3) . ?
C10 H10 0.95 . ?
C11 C12 1.389(3) . ?
C11 H11 0.95 . ?
C12 C13 1.383(2) . ?
C12 H12 0.95 . ?
C14 C15 1.399(2) . ?
C14 C19 1.402(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.95 . ?
C16 C17 1.387(2) . ?
C16 H16 0.95 . ?
C17 C18 1.378(2) . ?
C17 H17 0.95 . ?
C18 C19 1.417(2) . ?
C18 C26 1.478(2) . ?
C19 C20 1.500(2) . ?
C20 O2 1.231(2) . ?
C20 C21 1.489(3) . ?
C21 C22 1.385(3) . ?
C21 C26 1.395(3) . ?
C22 C23 1.398(3) . ?
C22 H22 0.95 . ?
C23 C24 1.381(3) . ?
C23 H23 0.95 . ?
C24 C25 1.395(3) . ?
C24 H24 0.95 . ?
C25 C26 1.382(3) . ?
C25 H25 0.95 . ?
O1 H1 0.94(2) . ?


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
O1 C1 C2 107.37(14) . . ?
O1 C1 C13 113.95(14) . . ?
C2 C1 C13 101.31(13) . . ?
O1 C1 C14 112.75(14) . . ?
C2 C1 C14 112.33(14) . . ?
C13 C1 C14 108.62(13) . . ?
C3 C2 C7 120.79(17) . . ?
C3 C2 C1 127.92(16) . . ?
C7 C2 C1 111.28(15) . . ?
C4 C3 C2 118.42(18) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 120.87(18) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.97(18) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 118.57(18) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C2 120.38(17) . . ?
C6 C7 C8 131.32(17) . . ?
C2 C7 C8 108.23(15) . . ?
C9 C8 C13 119.98(17) . . ?
C9 C8 C7 131.22(17) . . ?
C13 C8 C7 108.78(15) . . ?
C10 C9 C8 118.53(18) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 121.24(18) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.58(18) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 118.59(18) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C8 121.07(17) . . ?
C12 C13 C1 128.68(16) . . ?
C8 C13 C1 110.22(15) . . ?
C15 C14 C19 116.19(15) . . ?
C15 C14 C1 118.62(15) . . ?
C19 C14 C1 125.15(15) . . ?
C16 C15 C14 122.63(16) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C15 C16 C17 121.11(17) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 117.75(16) . . ?
C18 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
C17 C18 C19 121.58(16) . . ?
C17 C18 C26 128.92(16) . . ?
C19 C18 C26 109.49(16) . . ?
C14 C19 C18 120.71(16) . . ?
C14 C19 C20 132.52(16) . . ?
C18 C19 C20 106.75(15) . . ?
O2 C20 C21 125.28(17) . . ?
O2 C20 C19 128.16(17) . . ?
C21 C20 C19 106.54(15) . . ?
C22 C21 C26 122.09(18) . . ?
C22 C21 C20 129.28(19) . . ?
C26 C21 C20 108.62(15) . . ?
C21 C22 C23 117.1(2) . . ?
C21 C22 H22 121.4 . . ?
C23 C22 H22 121.4 . . ?
C24 C23 C22 121.05(19) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 121.3(2) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 118.1(2) . . ?
C26 C25 H25 121 . . ?
C24 C25 H25 121 . . ?
C25 C26 C21 120.26(17) . . ?
C25 C26 C18 131.19(18) . . ?
C21 C26 C18 108.55(16) . . ?
C1 O1 H1 107.7(13) . . ?


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 55.1(2) . . . . ?
C13 C1 C2 C3 174.88(17) . . . . ?
C14 C1 C2 C3 -69.4(2) . . . . ?
O1 C1 C2 C7 -123.41(15) . . . . ?
C13 C1 C2 C7 -3.64(17) . . . . ?
C14 C1 C2 C7 112.08(16) . . . . ?
C7 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C4 -178.25(16) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C5 C6 C7 C8 175.87(18) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C1 C2 C7 C6 179.16(15) . . . . ?
C3 C2 C7 C8 -176.82(15) . . . . ?
C1 C2 C7 C8 1.82(19) . . . . ?
C6 C7 C8 C9 2.4(3) . . . . ?
C2 C7 C8 C9 179.30(18) . . . . ?
C6 C7 C8 C13 -175.89(18) . . . . ?
C2 C7 C8 C13 1.05(19) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 -177.85(18) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C8 0.9(3) . . . . ?
C11 C12 C13 C1 -177.49(16) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C7 C8 C13 C12 177.91(15) . . . . ?
C9 C8 C13 C1 178.05(15) . . . . ?
C7 C8 C13 C1 -3.47(19) . . . . ?
O1 C1 C13 C12 -62.3(2) . . . . ?
C2 C1 C13 C12 -177.24(17) . . . . ?
C14 C1 C13 C12 64.3(2) . . . . ?
O1 C1 C13 C8 119.23(16) . . . . ?
C2 C1 C13 C8 4.27(17) . . . . ?
C14 C1 C13 C8 -114.16(15) . . . . ?
O1 C1 C14 C15 -146.77(15) . . . . ?
C2 C1 C14 C15 -25.3(2) . . . . ?
C13 C1 C14 C15 85.94(18) . . . . ?
O1 C1 C14 C19 35.6(2) . . . . ?
C2 C1 C14 C19 157.11(15) . . . . ?
C13 C1 C14 C19 -91.66(19) . . . . ?
C19 C14 C15 C16 -1.4(2) . . . . ?
C1 C14 C15 C16 -179.26(15) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C16 C17 C18 C26 179.07(16) . . . . ?
C15 C14 C19 C18 1.9(2) . . . . ?
C1 C14 C19 C18 179.57(15) . . . . ?
C15 C14 C19 C20 -176.03(16) . . . . ?
C1 C14 C19 C20 1.6(3) . . . . ?
C17 C18 C19 C14 -1.0(2) . . . . ?
C26 C18 C19 C14 179.33(14) . . . . ?
C17 C18 C19 C20 177.45(15) . . . . ?
C26 C18 C19 C20 -2.25(18) . . . . ?
C14 C19 C20 O2 1.7(3) . . . . ?
C18 C19 C20 O2 -176.49(18) . . . . ?
C14 C19 C20 C21 -179.76(17) . . . . ?
C18 C19 C20 C21 2.08(17) . . . . ?
O2 C20 C21 C22 -3.5(3) . . . . ?
C19 C20 C21 C22 177.84(18) . . . . ?
O2 C20 C21 C26 177.49(17) . . . . ?
C19 C20 C21 C26 -1.14(18) . . . . ?
C26 C21 C22 C23 0.2(3) . . . . ?
C20 C21 C22 C23 -178.65(17) . . . . ?
C21 C22 C23 C24 -1.2(3) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C24 C25 C26 C21 -0.9(3) . . . . ?
C24 C25 C26 C18 179.24(17) . . . . ?
C22 C21 C26 C25 0.8(3) . . . . ?
C20 C21 C26 C25 179.90(15) . . . . ?
C22 C21 C26 C18 -179.28(16) . . . . ?
C20 C21 C26 C18 -0.21(19) . . . . ?
C17 C18 C26 C25 1.8(3) . . . . ?
C19 C18 C26 C25 -178.54(18) . . . . ?
C17 C18 C26 C21 -178.09(17) . . . . ?
C19 C18 C26 C21 1.59(19) . . . . ?


#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR HM110                                                #
#----------------------------------------------------------------------------#
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZF_I2
_database_code_depnum_ccdc_archive 'CCDC 1475309'
_audit_update_record             
;
2016-04-19 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                              CHEMICAL_INFORMATION                          #
#----------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H5 I2 N O'
_chemical_formula_sum            'C12 H5 I2 N O'
_chemical_formula_weight         432.97
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      Monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.4324(15)
_cell_length_b                   4.1685(4)
_cell_length_c                   15.7648(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.635(4)
_cell_angle_gamma                90
_cell_volume                     1140.04(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    6958
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       stick
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.523
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             792
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    5.492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_T_max  0.803

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0443
_diffrn_reflns_av_uneti/neti     0.0393
_diffrn_reflns_number            11373
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.326
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             2610
_reflns_number_gt                2404
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CRYSCALc (T. Roisnel, local program, 2015)'

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

_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     
'w=1/[σ²(Fo²)+(0.0482P)²+9.0043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2610
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.480
_refine_diff_density_min         -1.672
_refine_diff_density_rms         0.222




# ............... End of .HKL file ...........................................
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                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 0.0000 0.0000 '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 0.0060 '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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1329(3) 0.9103(14) 0.3164(4) 0.0185(11) Uani 1 1 d . . . . .
C2 C 0.0916(4) 0.9941(16) 0.2390(4) 0.0239(13) Uani 1 1 d . . . . .
H2 H 0.0452 1.1134 0.2395 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1168(4) 0.9074(18) 0.1617(4) 0.0279(14) Uani 1 1 d . . . . .
H3 H 0.0874 0.9641 0.1099 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1855(4) 0.7368(17) 0.1597(4) 0.0255(14) Uani 1 1 d . . . . .
H4 H 0.2031 0.6747 0.1070 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2272(3) 0.6602(15) 0.2358(4) 0.0201(12) Uani 1 1 d . . . . .
C6 C 0.3020(4) 0.4888(15) 0.2504(4) 0.0204(12) Uani 1 1 d . . . . .
O7 O 0.3405(3) 0.3919(13) 0.1956(3) 0.0312(11) Uani 1 1 d . . . . .
C8 C 0.3194(3) 0.4693(14) 0.3458(4) 0.0171(11) Uani 1 1 d . . . . .
C9 C 0.3800(3) 0.3435(14) 0.3969(4) 0.0175(11) Uani 1 1 d . . . . .
C10 C 0.3799(4) 0.3725(16) 0.4853(4) 0.0247(13) Uani 1 1 d . . . . .
H10 H 0.4204 0.2858 0.5231 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3180(4) 0.5335(17) 0.5158(4) 0.0270(14) Uani 1 1 d . . . . .
H11 H 0.3185 0.5547 0.5759 0.032 Uiso 1 1 calc R U . . .
N12 N 0.2577(3) 0.6616(14) 0.4676(3) 0.0225(11) Uani 1 1 d . . . . .
C13 C 0.2598(3) 0.6244(14) 0.3833(4) 0.0159(11) Uani 1 1 d . . . . .
C14 C 0.2018(3) 0.7453(14) 0.3158(4) 0.0166(11) Uani 1 1 d . . . . .
I1 I 0.08654(2) 1.04792(10) 0.42947(3) 0.02432(14) Uani 1 1 d . . . . .
I2 I 0.47374(2) 0.11933(9) 0.34799(3) 0.02369(14) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                               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
C1 C14 1.384(8) . ?
C1 C2 1.399(9) . ?
C1 I1 2.108(6) . ?
C2 C3 1.384(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(9) . ?
C4 H4 0.9500 . ?
C5 C14 1.423(8) . ?
C5 C6 1.485(9) . ?
C6 O7 1.214(8) . ?
C6 C8 1.508(8) . ?
C8 C9 1.368(8) . ?
C8 C13 1.402(8) . ?
C9 C10 1.399(8) . ?
C9 I2 2.095(6) . ?
C10 C11 1.396(9) . ?
C10 H10 0.9500 . ?
C11 N12 1.347(8) . ?
C11 H11 0.9500 . ?
N12 C13 1.342(8) . ?
C13 C14 1.483(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 119.4(6) . . ?
C14 C1 I1 123.1(4) . . ?
C2 C1 I1 117.6(5) . . ?
C3 C2 C1 121.5(6) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 118.6(6) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C14 122.1(6) . . ?
C4 C5 C6 128.8(6) . . ?
C14 C5 C6 109.1(5) . . ?
O7 C6 C5 126.1(6) . . ?
O7 C6 C8 128.4(6) . . ?
C5 C6 C8 105.5(5) . . ?
C9 C8 C13 119.3(5) . . ?
C9 C8 C6 132.5(6) . . ?
C13 C8 C6 108.1(5) . . ?
C8 C9 C10 118.5(6) . . ?
C8 C9 I2 122.7(4) . . ?
C10 C9 I2 118.8(5) . . ?
C11 C10 C9 117.4(6) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
N12 C11 C10 125.7(6) . . ?
N12 C11 H11 117.2 . . ?
C10 C11 H11 117.2 . . ?
C13 N12 C11 114.7(5) . . ?
N12 C13 C8 124.3(6) . . ?
N12 C13 C14 126.0(5) . . ?
C8 C13 C14 109.6(5) . . ?
C1 C14 C5 118.4(5) . . ?
C1 C14 C13 134.1(5) . . ?
C5 C14 C13 107.6(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
C14 C1 C2 C3 2.0(9) . . . . ?
I1 C1 C2 C3 -178.5(5) . . . . ?
C1 C2 C3 C4 -1.0(10) . . . . ?
C2 C3 C4 C5 -0.5(10) . . . . ?
C3 C4 C5 C14 1.0(10) . . . . ?
C3 C4 C5 C6 -178.4(6) . . . . ?
C4 C5 C6 O7 1.8(11) . . . . ?
C14 C5 C6 O7 -177.7(6) . . . . ?
C4 C5 C6 C8 -179.3(6) . . . . ?
C14 C5 C6 C8 1.3(6) . . . . ?
O7 C6 C8 C9 -0.2(11) . . . . ?
C5 C6 C8 C9 -179.1(6) . . . . ?
O7 C6 C8 C13 177.7(6) . . . . ?
C5 C6 C8 C13 -1.2(6) . . . . ?
C13 C8 C9 C10 0.5(9) . . . . ?
C6 C8 C9 C10 178.2(6) . . . . ?
C13 C8 C9 I2 -178.1(4) . . . . ?
C6 C8 C9 I2 -0.4(9) . . . . ?
C8 C9 C10 C11 -0.9(9) . . . . ?
I2 C9 C10 C11 177.7(5) . . . . ?
C9 C10 C11 N12 0.7(11) . . . . ?
C10 C11 N12 C13 0.1(10) . . . . ?
C11 N12 C13 C8 -0.6(9) . . . . ?
C11 N12 C13 C14 -179.0(6) . . . . ?
C9 C8 C13 N12 0.3(9) . . . . ?
C6 C8 C13 N12 -177.9(6) . . . . ?
C9 C8 C13 C14 179.0(5) . . . . ?
C6 C8 C13 C14 0.7(6) . . . . ?
C2 C1 C14 C5 -1.5(8) . . . . ?
I1 C1 C14 C5 179.1(4) . . . . ?
C2 C1 C14 C13 179.0(6) . . . . ?
I1 C1 C14 C13 -0.4(10) . . . . ?
C4 C5 C14 C1 0.0(9) . . . . ?
C6 C5 C14 C1 179.5(5) . . . . ?
C4 C5 C14 C13 179.6(6) . . . . ?
C6 C5 C14 C13 -0.8(6) . . . . ?
N12 C13 C14 C1 -1.8(11) . . . . ?
C8 C13 C14 C1 179.6(6) . . . . ?
N12 C13 C14 C5 178.6(6) . . . . ?
C8 C13 C14 C5 0.1(7) . . . . ?

#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR AZF_I2                                               #
#----------------------------------------------------------------------------#
