# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_D1A2
_database_code_depnum_ccdc_archive 'CCDC 1037236'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-SC-2 2,3,5,6-Me4-pyrazine-1,4-dioxide, I-(CF2)2-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H12 N2 O2) (C2 F4 I2)
;
_chemical_formula_sum            'C10 H12 F4 I2 N2 O2'
_chemical_formula_weight         522.02

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'
F F 0.0171 0.0103 '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                   8.6275(16)
_cell_length_b                   12.005(2)
_cell_length_c                   8.3466(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.080(5)
_cell_angle_gamma                90.00
_cell_volume                     762.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8521
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      31.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    4.167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3883
_exptl_absorpt_correction_T_max  0.6807
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11427
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         32.03
_reflns_number_total             2488
_reflns_number_gt                2326
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0200P)²+1.5000P] 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         2488
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0527
_refine_ls_wR_factor_gt          0.0517
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
N11 N 0.4733(2) 0.41717(14) 0.5946(2) 0.0169(3) Uani 1 1 d . . .
O11 O 0.4479(2) 0.33848(14) 0.6876(2) 0.0269(4) Uani 1 1 d . . .
C12 C 0.3817(3) 0.51464(18) 0.5647(3) 0.0183(4) Uani 1 1 d . . .
C16 C 0.5921(3) 0.40132(17) 0.5327(3) 0.0172(4) Uani 1 1 d . . .
C22 C 0.2614(3) 0.5211(3) 0.6456(4) 0.0306(5) Uani 1 1 d . . .
H22A H 0.1939 0.5905 0.6077 0.046 Uiso 1 1 calc R . .
H22B H 0.3301 0.5195 0.7784 0.046 Uiso 1 1 calc R . .
H22C H 0.1807 0.4575 0.6044 0.046 Uiso 1 1 calc R . .
C26 C 0.6843(3) 0.2916(2) 0.5756(3) 0.0269(5) Uani 1 1 d . . .
H26A H 0.7860 0.2958 0.5532 0.040 Uiso 1 1 calc R . .
H26B H 0.6036 0.2338 0.4982 0.040 Uiso 1 1 calc R . .
H26C H 0.7241 0.2732 0.7034 0.040 Uiso 1 1 calc R . .
C31 C 0.0660(3) 0.00824(17) 0.4644(3) 0.0172(4) Uani 1 1 d . . .
I1 I 0.214539(18) 0.161313(11) 0.552898(19) 0.02067(5) Uani 1 1 d . . .
F31A F 0.17877(18) -0.07890(11) 0.5208(2) 0.0239(3) Uani 1 1 d . . .
F31B F -0.02183(18) 0.00428(12) 0.28180(17) 0.0238(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 O11 1.305(2) . ?
N11 C16 1.361(3) . ?
N11 C12 1.367(3) . ?
C12 C16 1.379(3) 3_666 ?
C12 C22 1.484(3) . ?
C16 C12 1.379(3) 3_666 ?
C16 C26 1.493(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C31 F31B 1.346(2) . ?
C31 F31A 1.353(2) . ?
C31 C31 1.525(4) 3_556 ?
C31 I1 2.162(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
O11 N11 C16 119.45(19) . . ?
O11 N11 C12 118.96(19) . . ?
C16 N11 C12 121.57(18) . . ?
N11 C12 C16 119.54(19) . 3_666 ?
N11 C12 C22 115.4(2) . . ?
C16 C12 C22 125.0(2) 3_666 . ?
N11 C16 C12 118.88(18) . 3_666 ?
N11 C16 C26 116.4(2) . . ?
C12 C16 C26 124.7(2) 3_666 . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C26 H26A 109.5 . . ?
C16 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C16 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F31B C31 F31A 107.21(17) . . ?
F31B C31 C31 108.1(2) . 3_556 ?
F31A C31 C31 108.1(2) . 3_556 ?
F31B C31 I1 110.12(13) . . ?
F31A C31 I1 108.95(13) . . ?
C31 C31 I1 114.11(19) 3_556 . ?

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
O11 N11 C12 C16 179.71(18) . . . 3_666 ?
C16 N11 C12 C16 1.0(3) . . . 3_666 ?
O11 N11 C12 C22 0.7(3) . . . . ?
C16 N11 C12 C22 -178.00(19) . . . . ?
O11 N11 C16 C12 -179.70(18) . . . 3_666 ?
C12 N11 C16 C12 -1.0(3) . . . 3_666 ?
O11 N11 C16 C26 0.8(3) . . . . ?
C12 N11 C16 C26 179.53(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         2.752
_refine_diff_density_min         -1.138
_refine_diff_density_rms         0.110
####################################################################### 
# 
# 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_D2A1
_database_code_depnum_ccdc_archive 'CCDC 1037237'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
JB-1-2 pyrazine 1-oxide, I-(CF2)4-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C4 H4 N2 O) (C4 F8 I2)
;
_chemical_formula_sum            'C8 H4 F8 I2 N2 O'
_chemical_formula_weight         549.93

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'
F F 0.0171 0.0103 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.3515(5)
_cell_length_b                   11.1482(11)
_cell_length_c                   12.0159(12)
_cell_angle_alpha                85.076(2)
_cell_angle_beta                 80.408(3)
_cell_angle_gamma                84.424(2)
_cell_volume                     701.72(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      33.72

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    4.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3056
_exptl_absorpt_correction_T_max  0.5670
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18809
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         33.72
_reflns_number_total             5086
_reflns_number_gt                4597
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0300P)²+0.6000P] 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         5086
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.004
_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
N11 N 0.2103(4) 0.91687(18) 0.41343(17) 0.0212(4) Uani 1 1 d . . .
O11 O 0.3439(4) 0.86484(17) 0.48646(18) 0.0329(4) Uani 1 1 d . . .
C12 C 0.0198(5) 0.8614(2) 0.3824(2) 0.0240(4) Uani 1 1 d . . .
H12 H -0.0192 0.7834 0.4151 0.029 Uiso 1 1 calc R . .
C13 C -0.1150(5) 0.9197(2) 0.3033(2) 0.0262(5) Uani 1 1 d . . .
H13 H -0.2458 0.8795 0.2814 0.031 Uiso 1 1 calc R . .
N14 N -0.0722(4) 1.0300(2) 0.25533(19) 0.0272(4) Uani 1 1 d . . .
C15 C 0.1098(5) 1.0830(2) 0.2896(2) 0.0266(5) Uani 1 1 d . . .
H15 H 0.1415 1.1624 0.2586 0.032 Uiso 1 1 calc R . .
C16 C 0.2559(5) 1.0297(2) 0.3675(2) 0.0228(4) Uani 1 1 d . . .
H16 H 0.3857 1.0711 0.3887 0.027 Uiso 1 1 calc R . .
C21 C 0.7346(5) 0.5205(2) 0.7044(2) 0.0259(5) Uani 1 1 d . . .
I1 I 0.52687(3) 0.648915(13) 0.603365(13) 0.02507(5) Uani 1 1 d . . .
F21A F 0.8508(4) 0.58054(17) 0.77050(19) 0.0456(5) Uani 1 1 d . . .
F21B F 0.9179(4) 0.45778(19) 0.63683(18) 0.0471(5) Uani 1 1 d . . .
C22 C 0.5638(4) 0.4320(2) 0.7794(2) 0.0208(4) Uani 1 1 d . . .
F22A F 0.3593(3) 0.49395(16) 0.83250(14) 0.0312(3) Uani 1 1 d . . .
F22B F 0.4856(4) 0.35954(14) 0.71013(14) 0.0314(3) Uani 1 1 d . . .
C23 C 0.6940(4) 0.3521(2) 0.87010(19) 0.0195(4) Uani 1 1 d . . .
F23A F 0.7303(3) 0.42420(14) 0.94875(13) 0.0277(3) Uani 1 1 d . . .
F23B F 0.9221(3) 0.30584(14) 0.81994(14) 0.0264(3) Uani 1 1 d . . .
C24 C 0.5449(5) 0.2470(3) 0.9297(2) 0.0293(5) Uani 1 1 d . . .
I2 I 0.71420(3) 0.153426(14) 1.065633(13) 0.02523(5) Uani 1 1 d . . .
F24A F 0.3083(3) 0.2910(2) 0.96875(19) 0.0502(6) Uani 1 1 d . . .
F24B F 0.5297(5) 0.16858(17) 0.85182(17) 0.0473(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 O11 1.288(3) . ?
N11 C16 1.357(3) . ?
N11 C12 1.360(3) . ?
C12 C13 1.370(4) . ?
C12 H12 0.9500 . ?
C13 N14 1.337(4) . ?
C13 H13 0.9500 . ?
N14 C15 1.325(4) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 F21A 1.343(3) . ?
C21 F21B 1.345(3) . ?
C21 C22 1.540(3) . ?
C21 I1 2.145(2) . ?
C22 F22A 1.334(3) . ?
C22 F22B 1.347(3) . ?
C22 C23 1.560(3) . ?
C23 F23A 1.341(3) . ?
C23 F23B 1.344(3) . ?
C23 C24 1.540(3) . ?
C24 F24A 1.336(4) . ?
C24 F24B 1.351(3) . ?
C24 I2 2.143(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
O11 N11 C16 120.0(2) . . ?
O11 N11 C12 121.1(2) . . ?
C16 N11 C12 118.9(2) . . ?
N11 C12 C13 119.0(2) . . ?
N11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
N14 C13 C12 123.5(2) . . ?
N14 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C15 N14 C13 116.1(2) . . ?
N14 C15 C16 123.8(2) . . ?
N14 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
N11 C16 C15 118.6(2) . . ?
N11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
F21A C21 F21B 107.1(2) . . ?
F21A C21 C22 109.1(2) . . ?
F21B C21 C22 109.3(2) . . ?
F21A C21 I1 108.81(16) . . ?
F21B C21 I1 109.64(17) . . ?
C22 C21 I1 112.79(16) . . ?
F22A C22 F22B 108.17(19) . . ?
F22A C22 C21 109.18(19) . . ?
F22B C22 C21 107.2(2) . . ?
F22A C22 C23 108.18(19) . . ?
F22B C22 C23 108.98(18) . . ?
C21 C22 C23 114.9(2) . . ?
F23A C23 F23B 108.54(18) . . ?
F23A C23 C24 108.4(2) . . ?
F23B C23 C24 108.1(2) . . ?
F23A C23 C22 107.72(18) . . ?
F23B C23 C22 108.42(19) . . ?
C24 C23 C22 115.42(19) . . ?
F24A C24 F24B 107.6(2) . . ?
F24A C24 C23 108.3(2) . . ?
F24B C24 C23 108.3(2) . . ?
F24A C24 I2 109.74(18) . . ?
F24B C24 I2 109.41(18) . . ?
C23 C24 I2 113.37(15) . . ?

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
O11 N11 C12 C13 -179.2(2) . . . . ?
C16 N11 C12 C13 1.9(4) . . . . ?
N11 C12 C13 N14 -1.0(4) . . . . ?
C12 C13 N14 C15 -0.8(4) . . . . ?
C13 N14 C15 C16 1.7(4) . . . . ?
O11 N11 C16 C15 180.0(2) . . . . ?
C12 N11 C16 C15 -1.1(4) . . . . ?
N14 C15 C16 N11 -0.8(4) . . . . ?
F21A C21 C22 F22A 73.4(2) . . . . ?
F21B C21 C22 F22A -169.9(2) . . . . ?
I1 C21 C22 F22A -47.7(2) . . . . ?
F21A C21 C22 F22B -169.7(2) . . . . ?
F21B C21 C22 F22B -52.9(3) . . . . ?
I1 C21 C22 F22B 69.3(2) . . . . ?
F21A C21 C22 C23 -48.4(3) . . . . ?
F21B C21 C22 C23 68.4(3) . . . . ?
I1 C21 C22 C23 -169.40(16) . . . . ?
F22A C22 C23 F23A -52.2(3) . . . . ?
F22B C22 C23 F23A -169.56(18) . . . . ?
C21 C22 C23 F23A 70.1(3) . . . . ?
F22A C22 C23 F23B -169.45(17) . . . . ?
F22B C22 C23 F23B 73.2(2) . . . . ?
C21 C22 C23 F23B -47.2(3) . . . . ?
F22A C22 C23 C24 69.1(3) . . . . ?
F22B C22 C23 C24 -48.3(3) . . . . ?
C21 C22 C23 C24 -168.6(2) . . . . ?
F23A C23 C24 F24A 69.4(2) . . . . ?
F23B C23 C24 F24A -173.1(2) . . . . ?
C22 C23 C24 F24A -51.5(3) . . . . ?
F23A C23 C24 F24B -174.3(2) . . . . ?
F23B C23 C24 F24B -56.8(2) . . . . ?
C22 C23 C24 F24B 64.8(3) . . . . ?
F23A C23 C24 I2 -52.7(2) . . . . ?
F23B C23 C24 I2 64.8(2) . . . . ?
C22 C23 C24 I2 -173.59(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.906
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.969
_refine_diff_density_rms         0.180
####################################################################### 
# 
# 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_D2A2
_database_code_depnum_ccdc_archive 'CCDC 1037238'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
JB-1-34 2,3,5,6-Me4-pyrazine-1,4-dioxide, I-(CF2)4-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H12 N2 O2) (C4 F8 I2)
;
_chemical_formula_sum            'C12 H12 F8 I2 N2 O2'
_chemical_formula_weight         622.04

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'
F F 0.0171 0.0103 '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                   9.3817(10)
_cell_length_b                   12.8620(14)
_cell_length_c                   8.1127(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.521(3)
_cell_angle_gamma                90.00
_cell_volume                     916.82(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8345
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      32.95

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    3.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3336
_exptl_absorpt_correction_T_max  0.7662
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11185
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         32.95
_reflns_number_total             3188
_reflns_number_gt                2911
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0300P)²+0.6000P] 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         3188
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0615
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
N11 N -0.00236(19) 0.43226(13) 0.3705(2) 0.0281(3) Uani 1 1 d . . .
O11 O -0.0043(2) 0.36709(14) 0.2468(2) 0.0403(4) Uani 1 1 d . . .
C12 C 0.0847(2) 0.52008(16) 0.3960(3) 0.0300(4) Uani 1 1 d . . .
C16 C -0.0878(2) 0.41201(15) 0.4721(3) 0.0291(4) Uani 1 1 d . . .
C22 C 0.1691(3) 0.5349(2) 0.2725(4) 0.0474(6) Uani 1 1 d . . .
H22A H 0.2245 0.6010 0.2984 0.071 Uiso 1 1 calc R . .
H22B H 0.0970 0.5358 0.1512 0.071 Uiso 1 1 calc R . .
H22C H 0.2414 0.4776 0.2868 0.071 Uiso 1 1 calc R . .
C26 C -0.1797(3) 0.3148(2) 0.4305(4) 0.0448(5) Uani 1 1 d . . .
H26A H -0.2575 0.3174 0.4854 0.067 Uiso 1 1 calc R . .
H26B H -0.1131 0.2548 0.4762 0.067 Uiso 1 1 calc R . .
H26C H -0.2290 0.3082 0.3027 0.067 Uiso 1 1 calc R . .
C31 C 0.4125(2) 0.11873(16) 0.3358(3) 0.0301(4) Uani 1 1 d . . .
I1 I 0.229922(14) 0.225315(10) 0.310328(16) 0.02818(5) Uani 1 1 d . . .
F31A F 0.54188(17) 0.17117(13) 0.3651(3) 0.0570(5) Uani 1 1 d . . .
F31B F 0.3852(2) 0.06611(13) 0.18391(18) 0.0500(4) Uani 1 1 d . . .
C32 C 0.4344(2) 0.03975(15) 0.4853(2) 0.0245(3) Uani 1 1 d . . .
F32A F 0.45979(17) 0.09231(11) 0.63496(16) 0.0391(3) Uani 1 1 d . . .
F32B F 0.30365(14) -0.01336(10) 0.44811(18) 0.0351(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 O11 1.303(2) . ?
N11 C16 1.361(3) . ?
N11 C12 1.366(3) . ?
C12 C16 1.374(3) 3_566 ?
C12 C22 1.491(3) . ?
C16 C12 1.374(3) 3_566 ?
C16 C26 1.489(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C31 F31A 1.335(2) . ?
C31 F31B 1.349(2) . ?
C31 C32 1.540(3) . ?
C31 I1 2.147(2) . ?
C32 F32A 1.336(2) . ?
C32 F32B 1.343(2) . ?
C32 C32 1.552(4) 3_656 ?

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
O11 N11 C16 119.40(18) . . ?
O11 N11 C12 119.63(18) . . ?
C16 N11 C12 120.96(17) . . ?
N11 C12 C16 119.43(18) . 3_566 ?
N11 C12 C22 115.7(2) . . ?
C16 C12 C22 124.8(2) 3_566 . ?
N11 C16 C12 119.60(18) . 3_566 ?
N11 C16 C26 116.2(2) . . ?
C12 C16 C26 124.2(2) 3_566 . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C26 H26A 109.5 . . ?
C16 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C16 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F31A C31 F31B 106.62(18) . . ?
F31A C31 C32 109.30(17) . . ?
F31B C31 C32 108.58(17) . . ?
F31A C31 I1 109.85(14) . . ?
F31B C31 I1 110.06(14) . . ?
C32 C31 I1 112.27(12) . . ?
F32A C32 F32B 108.60(15) . . ?
F32A C32 C31 108.31(16) . . ?
F32B C32 C31 107.42(15) . . ?
F32A C32 C32 108.33(19) . 3_656 ?
F32B C32 C32 108.17(19) . 3_656 ?
C31 C32 C32 115.82(18) . 3_656 ?

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
O11 N11 C12 C16 -179.25(18) . . . 3_566 ?
C16 N11 C12 C16 1.1(3) . . . 3_566 ?
O11 N11 C12 C22 1.5(3) . . . . ?
C16 N11 C12 C22 -178.2(2) . . . . ?
O11 N11 C16 C12 179.25(18) . . . 3_566 ?
C12 N11 C16 C12 -1.1(3) . . . 3_566 ?
O11 N11 C16 C26 -0.5(3) . . . . ?
C12 N11 C16 C26 179.12(19) . . . . ?
F31A C31 C32 F32A 64.7(2) . . . . ?
F31B C31 C32 F32A -179.35(16) . . . . ?
I1 C31 C32 F32A -57.43(17) . . . . ?
F31A C31 C32 F32B -178.15(17) . . . . ?
F31B C31 C32 F32B -62.2(2) . . . . ?
I1 C31 C32 F32B 59.70(17) . . . . ?
F31A C31 C32 C32 -57.2(3) . . . 3_656 ?
F31B C31 C32 C32 58.8(2) . . . 3_656 ?
I1 C31 C32 C32 -179.31(17) . . . 3_656 ?

_diffrn_measured_fraction_theta_max 0.924
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.776
_refine_diff_density_min         -1.122
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_D3A2
_database_code_depnum_ccdc_archive 'CCDC 1037239'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
JB-1-35 2,3,5,6-Me4-pyrazine-1,4-dioxide, [I-(CF2)6-I]2
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H12 N2 O2) (C6 F12 I2)2
;
_chemical_formula_sum            'C20 H12 F24 I4 N2 O2'
_chemical_formula_weight         1275.92

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'
F F 0.0171 0.0103 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   12.3893(14)
_cell_length_b                   12.6332(14)
_cell_length_c                   13.1553(14)
_cell_angle_alpha                67.319(4)
_cell_angle_beta                 75.273(4)
_cell_angle_gamma                67.884(4)
_cell_volume                     1745.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9817
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      31.97

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1180
_exptl_absorpt_coefficient_mu    3.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3821
_exptl_absorpt_correction_T_max  0.5538
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38902
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         32.11
_reflns_number_total             11420
_reflns_number_gt                9437
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0600P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11420
_refine_ls_number_parameters     481
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.994
_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
N11_1 N 0.4036(3) 0.0987(3) 0.9984(2) 0.0362(6) Uani 1 1 d . . .
O11_1 O 0.3112(3) 0.1933(3) 0.9966(2) 0.0489(7) Uani 1 1 d . . .
C12_1 C 0.3919(3) -0.0019(3) 0.9930(3) 0.0385(7) Uani 1 1 d . . .
C16_1 C 0.5101(3) 0.1021(3) 1.0044(3) 0.0382(7) Uani 1 1 d . . .
C22_1 C 0.2723(4) 0.0057(5) 0.9856(5) 0.0657(13) Uani 1 1 d . . .
H22A_1 H 0.2195 0.0878 0.9787 0.099 Uiso 1 1 calc R . .
H22B_1 H 0.2445 -0.0514 1.0527 0.099 Uiso 1 1 calc R . .
H22C_1 H 0.2735 -0.0144 0.9203 0.099 Uiso 1 1 calc R . .
C26_1 C 0.5107(5) 0.2184(4) 1.0087(5) 0.0645(13) Uani 1 1 d . . .
H26A_1 H 0.5920 0.2161 1.0028 0.097 Uiso 1 1 calc R . .
H26B_1 H 0.4676 0.2298 1.0792 0.097 Uiso 1 1 calc R . .
H26C_1 H 0.4730 0.2854 0.9469 0.097 Uiso 1 1 calc R . .
C31_1 C 0.1631(4) 0.5217(4) 0.6590(4) 0.0548(11) Uani 1 1 d . . .
I1_1 I 0.23447(2) 0.37441(2) 0.79943(2) 0.04127(7) Uani 1 1 d D . .
F31A_1 F 0.1995(3) 0.6152(3) 0.6411(3) 0.0744(9) Uani 1 1 d D . .
F31B_1 F 0.0458(3) 0.5582(4) 0.6841(3) 0.0847(11) Uani 1 1 d D . .
C32_1 C 0.1885(4) 0.4934(5) 0.5490(4) 0.0540(10) Uani 1 1 d . . .
F32A_1 F 0.1084(3) 0.5779(4) 0.4841(3) 0.1011(15) Uani 1 1 d . . .
F32B_1 F 0.1721(3) 0.3866(3) 0.5730(3) 0.0693(9) Uani 1 1 d . . .
C33_1 C 0.3102(4) 0.4923(3) 0.4834(3) 0.0432(8) Uani 1 1 d . . .
F33A_1 F 0.3103(4) 0.6060(3) 0.4343(3) 0.0829(11) Uani 1 1 d . . .
F33B_1 F 0.3899(2) 0.4365(3) 0.5539(2) 0.0526(6) Uani 1 1 d . . .
C34_1 C 0.3460(4) 0.4292(4) 0.3943(3) 0.0461(8) Uani 1 1 d . . .
F34A_1 F 0.2567(3) 0.4739(4) 0.3351(3) 0.0859(12) Uani 1 1 d . . .
F34B_1 F 0.3611(3) 0.3117(3) 0.4475(3) 0.0692(9) Uani 1 1 d . . .
C35_1 C 0.4596(3) 0.4403(4) 0.3148(3) 0.0403(7) Uani 1 1 d . . .
F35A_1 F 0.4523(3) 0.5551(3) 0.2643(3) 0.0880(12) Uani 1 1 d . . .
F35B_1 F 0.5472(2) 0.3914(3) 0.3764(2) 0.0642(8) Uani 1 1 d . . .
C36_1 C 0.4929(4) 0.3778(6) 0.2277(4) 0.0618(14) Uani 1 1 d . . .
I2_1 I 0.65571(2) 0.38514(2) 0.12699(2) 0.04407(7) Uani 1 1 d D . .
F36A_1 F 0.4086(3) 0.4285(8) 0.1642(4) 0.167(3) Uani 1 1 d D . .
F36B_1 F 0.4974(5) 0.2625(5) 0.2771(4) 0.132(2) Uani 1 1 d D . .
N11_2 N 0.9326(2) 0.4399(3) -0.0041(2) 0.0316(5) Uani 1 1 d . . .
O11_2 O 0.8671(2) 0.3823(3) -0.0095(3) 0.0455(6) Uani 1 1 d . . .
C12_2 C 1.0139(3) 0.3828(3) 0.0671(3) 0.0335(6) Uani 1 1 d . . .
C16_2 C 0.9164(3) 0.5567(3) -0.0717(3) 0.0329(6) Uani 1 1 d . . .
C22_2 C 1.0228(4) 0.2558(4) 0.1375(4) 0.0537(10) Uani 1 1 d . . .
H22A_2 H 1.0249 0.2458 0.2147 0.081 Uiso 1 1 calc R . .
H22B_2 H 1.0948 0.2010 0.1109 0.081 Uiso 1 1 calc R . .
H22C_2 H 0.9546 0.2370 0.1332 0.081 Uiso 1 1 calc R . .
C26_2 C 0.8229(4) 0.6105(4) -0.1440(4) 0.0500(9) Uani 1 1 d . . .
H26A_2 H 0.7628 0.6785 -0.1235 0.075 Uiso 1 1 calc R . .
H26B_2 H 0.7873 0.5495 -0.1349 0.075 Uiso 1 1 calc R . .
H26C_2 H 0.8566 0.6392 -0.2216 0.075 Uiso 1 1 calc R . .
C31_2 C 0.9897(6) 0.1002(5) -0.2235(5) 0.0728(17) Uani 1 1 d . . .
I3_2 I 0.93818(3) 0.22786(3) -0.13745(3) 0.05237(8) Uani 1 1 d D . .
F31A_2 F 0.8995(4) 0.1035(7) -0.2587(6) 0.168(3) Uani 1 1 d D . .
F31B_2 F 1.0320(6) -0.0118(4) -0.1526(4) 0.145(3) Uani 1 1 d D . .
C32_2 C 1.0854(4) 0.1183(3) -0.3204(4) 0.0443(8) Uani 1 1 d . . .
F32A_2 F 1.0450(4) 0.2239(3) -0.3947(3) 0.0841(11) Uani 1 1 d . . .
F32B_2 F 1.1737(3) 0.1247(4) -0.2843(3) 0.0810(10) Uani 1 1 d . . .
C33_2 C 1.1383(5) 0.0217(4) -0.3791(4) 0.0588(12) Uani 1 1 d . . .
F33A_2 F 1.0560(5) -0.0140(6) -0.3865(5) 0.136(2) Uani 1 1 d . . .
F33B_2 F 1.2094(5) -0.0736(3) -0.3143(3) 0.125(2) Uani 1 1 d . . .
C34_2 C 1.2079(4) 0.0602(3) -0.4938(4) 0.0500(9) Uani 1 1 d . A .
F34A_2 F 1.1312(4) 0.1297(4) -0.5654(3) 0.1107(17) Uani 1 1 d . . .
F34B_2 F 1.2653(4) 0.1268(4) -0.4932(4) 0.1098(17) Uani 1 1 d . . .
C35_2 C 1.2916(5) -0.0419(4) -0.5374(4) 0.0566(11) Uani 1 1 d . . .
F35A_2 F 1.2467(5) -0.1276(4) -0.5119(4) 0.124(2) Uani 1 1 d . A .
F35B_2 F 1.3848(4) -0.0926(5) -0.4812(3) 0.121(2) Uani 1 1 d . A .
C36A_2 C 1.3396(5) -0.0067(4) -0.6597(4) 0.0644(14) Uani 0.844(5) 1 d PD A 1
I4A_2 I 1.48235(17) -0.14979(6) -0.70258(6) 0.0838(4) Uani 0.844(5) 1 d PD A 1
F36A_2 F 1.2505(5) 0.0203(5) -0.7185(4) 0.0923(16) Uani 0.844(5) 1 d PD A 1
F36B_2 F 1.3668(5) 0.0920(4) -0.6937(4) 0.0884(16) Uani 0.844(5) 1 d PD A 1
C36B_2 C 1.3396(5) -0.0067(4) -0.6597(4) 0.0644(14) Uani 0.156(5) 1 d PD A 2
I4B_2 I 1.4338(7) -0.1459(4) -0.7136(3) 0.0838(4) Uani 0.156(5) 1 d PD A 2
F36C_2 F 1.267(2) 0.079(2) -0.726(2) 0.0923(16) Uani 0.156(5) 1 d PD A 2
F36D_2 F 1.406(2) 0.0527(19) -0.646(2) 0.0884(16) Uani 0.156(5) 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
N11_1 O11_1 1.304(4) . ?
N11_1 C16_1 1.359(5) . ?
N11_1 C12_1 1.362(5) . ?
C12_1 C16_1 1.382(5) 2_657 ?
C12_1 C22_1 1.474(6) . ?
C16_1 C12_1 1.382(5) 2_657 ?
C16_1 C26_1 1.494(6) . ?
C22_1 H22A_1 0.9800 . ?
C22_1 H22B_1 0.9800 . ?
C22_1 H22C_1 0.9800 . ?
C26_1 H26A_1 0.9800 . ?
C26_1 H26B_1 0.9800 . ?
C26_1 H26C_1 0.9800 . ?
C31_1 F31A_1 1.337(6) . ?
C31_1 F31B_1 1.342(5) . ?
C31_1 C32_1 1.551(7) . ?
C31_1 I1_1 2.144(5) . ?
C32_1 F32A_1 1.335(5) . ?
C32_1 F32B_1 1.344(6) . ?
C32_1 C33_1 1.533(6) . ?
C33_1 F33A_1 1.330(5) . ?
C33_1 F33B_1 1.331(5) . ?
C33_1 C34_1 1.547(6) . ?
C34_1 F34A_1 1.332(5) . ?
C34_1 F34B_1 1.337(5) . ?
C34_1 C35_1 1.543(5) . ?
C35_1 F35A_1 1.320(5) . ?
C35_1 F35B_1 1.332(5) . ?
C35_1 C36_1 1.523(6) . ?
C36_1 F36A_1 1.314(7) . ?
C36_1 F36B_1 1.332(7) . ?
C36_1 I2_1 2.126(4) . ?
N11_2 O11_2 1.307(4) . ?
N11_2 C12_2 1.350(5) . ?
N11_2 C16_2 1.366(4) . ?
C12_2 C16_2 1.375(5) 2_765 ?
C12_2 C22_2 1.489(5) . ?
C16_2 C12_2 1.375(5) 2_765 ?
C16_2 C26_2 1.476(5) . ?
C22_2 H22A_2 0.9800 . ?
C22_2 H22B_2 0.9800 . ?
C22_2 H22C_2 0.9800 . ?
C26_2 H26A_2 0.9800 . ?
C26_2 H26B_2 0.9800 . ?
C26_2 H26C_2 0.9800 . ?
C31_2 F31A_2 1.295(8) . ?
C31_2 F31B_2 1.349(8) . ?
C31_2 C32_2 1.515(7) . ?
C31_2 I3_2 2.135(5) . ?
C32_2 F32A_2 1.314(5) . ?
C32_2 F32B_2 1.338(5) . ?
C32_2 C33_2 1.543(6) . ?
C33_2 F33A_2 1.299(7) . ?
C33_2 F33B_2 1.321(7) . ?
C33_2 C34_2 1.531(6) . ?
C34_2 F34B_2 1.293(6) . ?
C34_2 F34A_2 1.323(6) . ?
C34_2 C35_2 1.526(6) . ?
C35_2 F35A_2 1.293(6) . ?
C35_2 F35B_2 1.342(7) . ?
C35_2 C36A_2 1.517(6) . ?
C36A_2 F36B_2 1.296(6) . ?
C36A_2 F36A_2 1.371(7) . ?
C36A_2 I4A_2 2.142(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
O11_1 N11_1 C16_1 119.8(3) . . ?
O11_1 N11_1 C12_1 119.2(3) . . ?
C16_1 N11_1 C12_1 121.0(3) . . ?
N11_1 C12_1 C16_1 119.0(3) . 2_657 ?
N11_1 C12_1 C22_1 116.0(4) . . ?
C16_1 C12_1 C22_1 125.0(4) 2_657 . ?
N11_1 C16_1 C12_1 120.0(3) . 2_657 ?
N11_1 C16_1 C26_1 115.4(4) . . ?
C12_1 C16_1 C26_1 124.5(4) 2_657 . ?
C12_1 C22_1 H22A_1 109.5 . . ?
C12_1 C22_1 H22B_1 109.5 . . ?
H22A_1 C22_1 H22B_1 109.5 . . ?
C12_1 C22_1 H22C_1 109.5 . . ?
H22A_1 C22_1 H22C_1 109.5 . . ?
H22B_1 C22_1 H22C_1 109.5 . . ?
C16_1 C26_1 H26A_1 109.5 . . ?
C16_1 C26_1 H26B_1 109.5 . . ?
H26A_1 C26_1 H26B_1 109.5 . . ?
C16_1 C26_1 H26C_1 109.5 . . ?
H26A_1 C26_1 H26C_1 109.5 . . ?
H26B_1 C26_1 H26C_1 109.5 . . ?
F31A_1 C31_1 F31B_1 107.0(4) . . ?
F31A_1 C31_1 C32_1 108.9(4) . . ?
F31B_1 C31_1 C32_1 106.4(4) . . ?
F31A_1 C31_1 I1_1 110.2(4) . . ?
F31B_1 C31_1 I1_1 107.8(3) . . ?
C32_1 C31_1 I1_1 116.1(3) . . ?
F32A_1 C32_1 F32B_1 107.8(4) . . ?
F32A_1 C32_1 C33_1 107.7(4) . . ?
F32B_1 C32_1 C33_1 110.2(4) . . ?
F32A_1 C32_1 C31_1 107.5(4) . . ?
F32B_1 C32_1 C31_1 107.8(4) . . ?
C33_1 C32_1 C31_1 115.6(4) . . ?
F33A_1 C33_1 F33B_1 108.0(4) . . ?
F33A_1 C33_1 C32_1 108.1(4) . . ?
F33B_1 C33_1 C32_1 108.9(3) . . ?
F33A_1 C33_1 C34_1 109.0(3) . . ?
F33B_1 C33_1 C34_1 108.7(3) . . ?
C32_1 C33_1 C34_1 113.9(4) . . ?
F34A_1 C34_1 F34B_1 108.6(4) . . ?
F34A_1 C34_1 C35_1 109.2(3) . . ?
F34B_1 C34_1 C35_1 107.3(4) . . ?
F34A_1 C34_1 C33_1 107.6(4) . . ?
F34B_1 C34_1 C33_1 107.5(3) . . ?
C35_1 C34_1 C33_1 116.4(3) . . ?
F35A_1 C35_1 F35B_1 106.8(4) . . ?
F35A_1 C35_1 C36_1 108.9(4) . . ?
F35B_1 C35_1 C36_1 107.7(4) . . ?
F35A_1 C35_1 C34_1 110.1(4) . . ?
F35B_1 C35_1 C34_1 107.6(3) . . ?
C36_1 C35_1 C34_1 115.4(3) . . ?
F36A_1 C36_1 F36B_1 106.8(5) . . ?
F36A_1 C36_1 C35_1 108.0(5) . . ?
F36B_1 C36_1 C35_1 109.6(4) . . ?
F36A_1 C36_1 I2_1 109.3(3) . . ?
F36B_1 C36_1 I2_1 108.7(4) . . ?
C35_1 C36_1 I2_1 114.2(3) . . ?
O11_2 N11_2 C12_2 119.6(3) . . ?
O11_2 N11_2 C16_2 118.3(3) . . ?
C12_2 N11_2 C16_2 122.1(3) . . ?
N11_2 C12_2 C16_2 119.3(3) . 2_765 ?
N11_2 C12_2 C22_2 117.3(3) . . ?
C16_2 C12_2 C22_2 123.3(4) 2_765 . ?
N11_2 C16_2 C12_2 118.6(3) . 2_765 ?
N11_2 C16_2 C26_2 117.3(3) . . ?
C12_2 C16_2 C26_2 124.2(3) 2_765 . ?
C12_2 C22_2 H22A_2 109.5 . . ?
C12_2 C22_2 H22B_2 109.5 . . ?
H22A_2 C22_2 H22B_2 109.5 . . ?
C12_2 C22_2 H22C_2 109.5 . . ?
H22A_2 C22_2 H22C_2 109.5 . . ?
H22B_2 C22_2 H22C_2 109.5 . . ?
C16_2 C26_2 H26A_2 109.5 . . ?
C16_2 C26_2 H26B_2 109.5 . . ?
H26A_2 C26_2 H26B_2 109.5 . . ?
C16_2 C26_2 H26C_2 109.5 . . ?
H26A_2 C26_2 H26C_2 109.5 . . ?
H26B_2 C26_2 H26C_2 109.5 . . ?
F31A_2 C31_2 F31B_2 107.7(6) . . ?
F31A_2 C31_2 C32_2 109.1(5) . . ?
F31B_2 C31_2 C32_2 106.8(5) . . ?
F31A_2 C31_2 I3_2 110.0(4) . . ?
F31B_2 C31_2 I3_2 109.0(4) . . ?
C32_2 C31_2 I3_2 113.9(3) . . ?
F32A_2 C32_2 F32B_2 106.1(4) . . ?
F32A_2 C32_2 C31_2 108.6(4) . . ?
F32B_2 C32_2 C31_2 108.1(4) . . ?
F32A_2 C32_2 C33_2 108.6(4) . . ?
F32B_2 C32_2 C33_2 107.3(4) . . ?
C31_2 C32_2 C33_2 117.6(4) . . ?
F33A_2 C33_2 F33B_2 106.0(5) . . ?
F33A_2 C33_2 C34_2 109.7(4) . . ?
F33B_2 C33_2 C34_2 108.3(4) . . ?
F33A_2 C33_2 C32_2 109.8(4) . . ?
F33B_2 C33_2 C32_2 107.5(4) . . ?
C34_2 C33_2 C32_2 115.2(3) . . ?
F34B_2 C34_2 F34A_2 106.5(5) . . ?
F34B_2 C34_2 C35_2 109.5(4) . . ?
F34A_2 C34_2 C35_2 107.6(4) . . ?
F34B_2 C34_2 C33_2 109.3(4) . . ?
F34A_2 C34_2 C33_2 107.6(4) . . ?
C35_2 C34_2 C33_2 116.0(3) . . ?
F35A_2 C35_2 F35B_2 104.5(5) . . ?
F35A_2 C35_2 C36A_2 110.3(4) . . ?
F35B_2 C35_2 C36A_2 106.4(5) . . ?
F35A_2 C35_2 C34_2 111.2(4) . . ?
F35B_2 C35_2 C34_2 106.7(4) . . ?
C36A_2 C35_2 C34_2 116.8(4) . . ?
F36B_2 C36A_2 F36A_2 104.6(5) . . ?
F36B_2 C36A_2 C35_2 112.5(5) . . ?
F36A_2 C36A_2 C35_2 107.4(5) . . ?
F36B_2 C36A_2 I4A_2 111.4(4) . . ?
F36A_2 C36A_2 I4A_2 107.4(4) . . ?
C35_2 C36A_2 I4A_2 112.9(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
O11_1 N11_1 C12_1 C16_1 -179.6(3) . . . 2_657 ?
C16_1 N11_1 C12_1 C16_1 1.2(6) . . . 2_657 ?
O11_1 N11_1 C12_1 C22_1 -0.1(5) . . . . ?
C16_1 N11_1 C12_1 C22_1 -179.3(4) . . . . ?
O11_1 N11_1 C16_1 C12_1 179.6(3) . . . 2_657 ?
C12_1 N11_1 C16_1 C12_1 -1.2(6) . . . 2_657 ?
O11_1 N11_1 C16_1 C26_1 0.2(5) . . . . ?
C12_1 N11_1 C16_1 C26_1 179.4(4) . . . . ?
F31A_1 C31_1 C32_1 F32A_1 -75.5(5) . . . . ?
F31B_1 C31_1 C32_1 F32A_1 39.5(6) . . . . ?
I1_1 C31_1 C32_1 F32A_1 159.5(4) . . . . ?
F31A_1 C31_1 C32_1 F32B_1 168.6(4) . . . . ?
F31B_1 C31_1 C32_1 F32B_1 -76.4(4) . . . . ?
I1_1 C31_1 C32_1 F32B_1 43.6(5) . . . . ?
F31A_1 C31_1 C32_1 C33_1 44.8(5) . . . . ?
F31B_1 C31_1 C32_1 C33_1 159.8(4) . . . . ?
I1_1 C31_1 C32_1 C33_1 -80.2(5) . . . . ?
F32A_1 C32_1 C33_1 F33A_1 44.9(5) . . . . ?
F32B_1 C32_1 C33_1 F33A_1 162.2(4) . . . . ?
C31_1 C32_1 C33_1 F33A_1 -75.3(5) . . . . ?
F32A_1 C32_1 C33_1 F33B_1 162.0(4) . . . . ?
F32B_1 C32_1 C33_1 F33B_1 -80.6(4) . . . . ?
C31_1 C32_1 C33_1 F33B_1 41.9(5) . . . . ?
F32A_1 C32_1 C33_1 C34_1 -76.4(5) . . . . ?
F32B_1 C32_1 C33_1 C34_1 40.9(5) . . . . ?
C31_1 C32_1 C33_1 C34_1 163.4(4) . . . . ?
F33A_1 C33_1 C34_1 F34A_1 -71.8(5) . . . . ?
F33B_1 C33_1 C34_1 F34A_1 170.7(3) . . . . ?
C32_1 C33_1 C34_1 F34A_1 49.0(5) . . . . ?
F33A_1 C33_1 C34_1 F34B_1 171.4(4) . . . . ?
F33B_1 C33_1 C34_1 F34B_1 53.8(4) . . . . ?
C32_1 C33_1 C34_1 F34B_1 -67.8(4) . . . . ?
F33A_1 C33_1 C34_1 C35_1 51.1(5) . . . . ?
F33B_1 C33_1 C34_1 C35_1 -66.4(4) . . . . ?
C32_1 C33_1 C34_1 C35_1 171.9(3) . . . . ?
F34A_1 C34_1 C35_1 F35A_1 65.9(5) . . . . ?
F34B_1 C34_1 C35_1 F35A_1 -176.5(4) . . . . ?
C33_1 C34_1 C35_1 F35A_1 -56.1(5) . . . . ?
F34A_1 C34_1 C35_1 F35B_1 -178.0(4) . . . . ?
F34B_1 C34_1 C35_1 F35B_1 -60.5(4) . . . . ?
C33_1 C34_1 C35_1 F35B_1 59.9(5) . . . . ?
F34A_1 C34_1 C35_1 C36_1 -57.8(5) . . . . ?
F34B_1 C34_1 C35_1 C36_1 59.8(5) . . . . ?
C33_1 C34_1 C35_1 C36_1 -179.9(4) . . . . ?
F35A_1 C35_1 C36_1 F36A_1 -62.3(5) . . . . ?
F35B_1 C35_1 C36_1 F36A_1 -177.8(4) . . . . ?
C34_1 C35_1 C36_1 F36A_1 62.1(6) . . . . ?
F35A_1 C35_1 C36_1 F36B_1 -178.3(5) . . . . ?
F35B_1 C35_1 C36_1 F36B_1 66.2(5) . . . . ?
C34_1 C35_1 C36_1 F36B_1 -53.9(6) . . . . ?
F35A_1 C35_1 C36_1 I2_1 59.5(5) . . . . ?
F35B_1 C35_1 C36_1 I2_1 -56.0(4) . . . . ?
C34_1 C35_1 C36_1 I2_1 -176.1(3) . . . . ?
O11_2 N11_2 C12_2 C16_2 179.3(3) . . . 2_765 ?
C16_2 N11_2 C12_2 C16_2 -0.4(5) . . . 2_765 ?
O11_2 N11_2 C12_2 C22_2 -0.9(4) . . . . ?
C16_2 N11_2 C12_2 C22_2 179.4(3) . . . . ?
O11_2 N11_2 C16_2 C12_2 -179.3(3) . . . 2_765 ?
C12_2 N11_2 C16_2 C12_2 0.4(5) . . . 2_765 ?
O11_2 N11_2 C16_2 C26_2 1.8(4) . . . . ?
C12_2 N11_2 C16_2 C26_2 -178.5(3) . . . . ?
F31A_2 C31_2 C32_2 F32A_2 60.2(6) . . . . ?
F31B_2 C31_2 C32_2 F32A_2 176.4(5) . . . . ?
I3_2 C31_2 C32_2 F32A_2 -63.2(5) . . . . ?
F31A_2 C31_2 C32_2 F32B_2 174.9(5) . . . . ?
F31B_2 C31_2 C32_2 F32B_2 -69.0(5) . . . . ?
I3_2 C31_2 C32_2 F32B_2 51.5(5) . . . . ?
F31A_2 C31_2 C32_2 C33_2 -63.5(7) . . . . ?
F31B_2 C31_2 C32_2 C33_2 52.6(6) . . . . ?
I3_2 C31_2 C32_2 C33_2 173.1(4) . . . . ?
F32A_2 C32_2 C33_2 F33A_2 -84.5(6) . . . . ?
F32B_2 C32_2 C33_2 F33A_2 161.2(5) . . . . ?
C31_2 C32_2 C33_2 F33A_2 39.2(7) . . . . ?
F32A_2 C32_2 C33_2 F33B_2 160.7(5) . . . . ?
F32B_2 C32_2 C33_2 F33B_2 46.4(5) . . . . ?
C31_2 C32_2 C33_2 F33B_2 -75.6(6) . . . . ?
F32A_2 C32_2 C33_2 C34_2 39.9(6) . . . . ?
F32B_2 C32_2 C33_2 C34_2 -74.4(5) . . . . ?
C31_2 C32_2 C33_2 C34_2 163.6(5) . . . . ?
F33A_2 C33_2 C34_2 F34B_2 161.7(5) . . . . ?
F33B_2 C33_2 C34_2 F34B_2 -83.1(5) . . . . ?
C32_2 C33_2 C34_2 F34B_2 37.2(6) . . . . ?
F33A_2 C33_2 C34_2 F34A_2 46.5(6) . . . . ?
F33B_2 C33_2 C34_2 F34A_2 161.6(5) . . . . ?
C32_2 C33_2 C34_2 F34A_2 -78.0(6) . . . . ?
F33A_2 C33_2 C34_2 C35_2 -74.0(6) . . . . ?
F33B_2 C33_2 C34_2 C35_2 41.2(6) . . . . ?
C32_2 C33_2 C34_2 C35_2 161.5(5) . . . . ?
F34B_2 C34_2 C35_2 F35A_2 162.7(5) . . . . ?
F34A_2 C34_2 C35_2 F35A_2 -82.1(6) . . . . ?
C33_2 C34_2 C35_2 F35A_2 38.4(7) . . . . ?
F34B_2 C34_2 C35_2 F35B_2 49.2(6) . . . . ?
F34A_2 C34_2 C35_2 F35B_2 164.5(5) . . . . ?
C33_2 C34_2 C35_2 F35B_2 -75.0(6) . . . . ?
F34B_2 C34_2 C35_2 C36A_2 -69.6(6) . . . . ?
F34A_2 C34_2 C35_2 C36A_2 45.7(7) . . . . ?
C33_2 C34_2 C35_2 C36A_2 166.2(5) . . . . ?
F35A_2 C35_2 C36A_2 F36B_2 168.7(6) . . . . ?
F35B_2 C35_2 C36A_2 F36B_2 -78.5(6) . . . . ?
C34_2 C35_2 C36A_2 F36B_2 40.5(7) . . . . ?
F35A_2 C35_2 C36A_2 F36A_2 54.1(6) . . . . ?
F35B_2 C35_2 C36A_2 F36A_2 166.9(5) . . . . ?
C34_2 C35_2 C36A_2 F36A_2 -74.1(6) . . . . ?
F35A_2 C35_2 C36A_2 I4A_2 -64.1(6) . . . . ?
F35B_2 C35_2 C36A_2 I4A_2 48.7(5) . . . . ?
C34_2 C35_2 C36A_2 I4A_2 167.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.933
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.496
_refine_diff_density_min         -1.733
_refine_diff_density_rms         0.155
####################################################################### 
# 
# 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_A2
_database_code_depnum_ccdc_archive 'CCDC 1037240'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'TW-Pyr-bis-N-oxide 2,3,5,6-Me4-pyrazine-1,4-dioxideC8 H12 N2 O2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 N2 O2'
_chemical_formula_sum            'C8 H12 N2 O2'
_chemical_formula_weight         168.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           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                   3.8328(9)
_cell_length_b                   10.291(3)
_cell_length_c                   10.396(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.770(9)
_cell_angle_gamma                90.00
_cell_volume                     405.26(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2346
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      31.55

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             180
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4747
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         31.61
_reflns_number_total             1245
_reflns_number_gt                987
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0700P)²+0.0800P] 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         1245
_refine_ls_number_parameters     57
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
N11 N 0.4591(2) 0.59500(9) 0.40744(9) 0.0195(2) Uani 1 1 d . . .
O11 O 0.4215(2) 0.68517(8) 0.31937(8) 0.0249(2) Uani 1 1 d . . .
C12 C 0.3043(3) 0.47608(11) 0.37995(11) 0.0201(3) Uani 1 1 d . . .
C16 C 0.6548(3) 0.61959(11) 0.52646(10) 0.0197(3) Uani 1 1 d . . .
C22 C 0.0981(3) 0.46302(12) 0.24765(11) 0.0242(3) Uani 1 1 d . . .
H22A H -0.0110 0.3767 0.2382 0.036 Uiso 1 1 calc R . .
H22B H 0.2555 0.4740 0.1825 0.036 Uiso 1 1 calc R . .
H22C H -0.0864 0.5297 0.2349 0.036 Uiso 1 1 calc R . .
C26 C 0.8096(3) 0.75198(11) 0.54260(11) 0.0240(3) Uani 1 1 d . . .
H26A H 0.9607 0.7583 0.6274 0.036 Uiso 1 1 calc R . .
H26B H 0.6196 0.8163 0.5379 0.036 Uiso 1 1 calc R . .
H26C H 0.9506 0.7687 0.4732 0.036 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
N11 O11 1.2961(12) . ?
N11 C16 1.3691(14) . ?
N11 C12 1.3710(15) . ?
C12 C16 1.3762(16) 3_666 ?
C12 C22 1.4842(16) . ?
C16 C12 1.3762(16) 3_666 ?
C16 C26 1.4853(16) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 N11 C16 119.52(9) . . ?
O11 N11 C12 119.59(9) . . ?
C16 N11 C12 120.89(9) . . ?
N11 C12 C16 119.48(10) . 3_666 ?
N11 C12 C22 115.24(10) . . ?
C16 C12 C22 125.28(10) 3_666 . ?
N11 C16 C12 119.63(10) . 3_666 ?
N11 C16 C26 115.21(10) . . ?
C12 C16 C26 125.15(10) 3_666 . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C26 H26A 109.5 . . ?
C16 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C16 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
O11 N11 C12 C16 179.87(9) . . . 3_666 ?
C16 N11 C12 C16 0.25(17) . . . 3_666 ?
O11 N11 C12 C22 -0.75(15) . . . . ?
C16 N11 C12 C22 179.64(9) . . . . ?
O11 N11 C16 C12 -179.87(9) . . . 3_666 ?
C12 N11 C16 C12 -0.25(17) . . . 3_666 ?
O11 N11 C16 C26 -0.10(14) . . . . ?
C12 N11 C16 C26 179.51(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.913
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_A5
_database_code_depnum_ccdc_archive 'CCDC 1037241'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-4py-der 1,1'-di[(4-pyridyl)methyl]-2,2'-biimidazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N6'
_chemical_formula_sum            'C18 H16 N6'
_chemical_formula_weight         316.37

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'

_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                   5.1637(9)
_cell_length_b                   16.705(3)
_cell_length_c                   9.1021(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.398(6)
_cell_angle_gamma                90.00
_cell_volume                     776.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4234
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      31.56

_exptl_crystal_description       prism
_exptl_crystal_colour            bronze
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9664
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7122
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         31.61
_reflns_number_total             2402
_reflns_number_gt                2092
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2402
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1653
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   1.319
_refine_ls_restrained_S_all      1.319
_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
N11 N 0.24061(17) 0.43365(4) 0.55817(9) 0.0174(2) Uani 1 1 d . . .
C12 C 0.40664(18) 0.46907(5) 0.47346(10) 0.0165(2) Uani 1 1 d . . .
N13 N 0.37463(18) 0.43924(5) 0.33706(9) 0.0203(2) Uani 1 1 d . . .
C14 C 0.1859(2) 0.38168(6) 0.33511(11) 0.0223(2) Uani 1 1 d . . .
H14 H 0.1224 0.3495 0.2516 0.027 Uiso 1 1 calc R . .
C15 C 0.1013(2) 0.37706(6) 0.47031(11) 0.0217(2) Uani 1 1 d . . .
H15 H -0.0278 0.3418 0.4979 0.026 Uiso 1 1 calc R . .
N21 N 0.7643(2) 0.29812(5) 1.00473(10) 0.0256(2) Uani 1 1 d . . .
C22 C 0.5978(2) 0.34890(6) 1.05658(12) 0.0254(3) Uani 1 1 d . . .
H22 H 0.6007 0.3521 1.1610 0.030 Uiso 1 1 calc R . .
C23 C 0.4232(2) 0.39664(5) 0.96755(10) 0.0218(2) Uani 1 1 d . . .
H23 H 0.3113 0.4321 1.0104 0.026 Uiso 1 1 calc R . .
C24 C 0.41190(19) 0.39249(5) 0.81397(10) 0.0169(2) Uani 1 1 d . . .
C25 C 0.5808(2) 0.33958(5) 0.75881(11) 0.0209(2) Uani 1 1 d . . .
H25 H 0.5788 0.3340 0.6548 0.025 Uiso 1 1 calc R . .
C26 C 0.7521(2) 0.29505(6) 0.85736(11) 0.0244(3) Uani 1 1 d . . .
H26 H 0.8688 0.2599 0.8176 0.029 Uiso 1 1 calc R . .
C27 C 0.22150(19) 0.44417(5) 0.71514(10) 0.0181(2) Uani 1 1 d . . .
H27A H 0.0413 0.4310 0.7322 0.022 Uiso 1 1 calc R . .
H27B H 0.2548 0.5010 0.7423 0.022 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
N11 C12 1.3684(11) . ?
N11 C15 1.3722(12) . ?
N11 C27 1.4571(11) . ?
C12 N13 1.3255(12) . ?
C12 C12 1.4474(18) 3_666 ?
N13 C14 1.3674(13) . ?
C14 C15 1.3667(13) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.3346(13) . ?
N21 C22 1.3416(13) . ?
C22 C23 1.3755(15) . ?
C22 H22 0.9500 . ?
C23 C24 1.3923(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.3864(12) . ?
C24 C27 1.5042(14) . ?
C25 C26 1.3814(15) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?

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
C12 N11 C15 106.72(7) . . ?
C12 N11 C27 129.65(8) . . ?
C15 N11 C27 123.35(7) . . ?
N13 C12 N11 111.26(8) . . ?
N13 C12 C12 124.53(10) . 3_666 ?
N11 C12 C12 124.21(10) . 3_666 ?
C12 N13 C14 105.52(8) . . ?
C15 C14 N13 110.42(9) . . ?
C15 C14 H14 124.8 . . ?
N13 C14 H14 124.8 . . ?
C14 C15 N11 106.06(8) . . ?
C14 C15 H15 127.0 . . ?
N11 C15 H15 127.0 . . ?
C26 N21 C22 116.06(9) . . ?
N21 C22 C23 123.91(9) . . ?
N21 C22 H22 118.0 . . ?
C23 C22 H22 118.0 . . ?
C22 C23 C24 119.36(8) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 117.33(9) . . ?
C25 C24 C27 122.69(8) . . ?
C23 C24 C27 119.98(7) . . ?
C26 C25 C24 119.02(9) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
N21 C26 C25 124.31(8) . . ?
N21 C26 H26 117.8 . . ?
C25 C26 H26 117.8 . . ?
N11 C27 C24 112.66(7) . . ?
N11 C27 H27A 109.1 . . ?
C24 C27 H27A 109.1 . . ?
N11 C27 H27B 109.1 . . ?
C24 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?

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
C15 N11 C12 N13 1.50(11) . . . . ?
C27 N11 C12 N13 175.48(8) . . . . ?
C15 N11 C12 C12 -178.34(11) . . . 3_666 ?
C27 N11 C12 C12 -4.35(18) . . . 3_666 ?
N11 C12 N13 C14 -1.26(11) . . . . ?
C12 C12 N13 C14 178.57(11) 3_666 . . . ?
C12 N13 C14 C15 0.56(12) . . . . ?
N13 C14 C15 N11 0.34(12) . . . . ?
C12 N11 C15 C14 -1.07(11) . . . . ?
C27 N11 C15 C14 -175.53(9) . . . . ?
C26 N21 C22 C23 -0.56(17) . . . . ?
N21 C22 C23 C24 0.87(17) . . . . ?
C22 C23 C24 C25 -0.09(14) . . . . ?
C22 C23 C24 C27 179.85(9) . . . . ?
C23 C24 C25 C26 -0.90(14) . . . . ?
C27 C24 C25 C26 179.16(9) . . . . ?
C22 N21 C26 C25 -0.53(16) . . . . ?
C24 C25 C26 N21 1.28(16) . . . . ?
C12 N11 C27 C24 -84.40(11) . . . . ?
C15 N11 C27 C24 88.71(11) . . . . ?
C25 C24 C27 N11 -1.51(13) . . . . ?
C23 C24 C27 N11 178.56(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.920
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.087

#END
