# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_3abn_tfib
_database_code_depnum_ccdc_archive 'CCDC 1494268'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C6 F4 I2, C7 H6 N2 '
_chemical_formula_sum            'C13 H6 F4 I2 N2'
_chemical_formula_weight         520.00

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4368(10)
_cell_length_b                   8.4962(2)
_cell_length_c                   11.8803(10)
_cell_angle_alpha                100.565(11)
_cell_angle_beta                 107.57
_cell_angle_gamma                105.95
_cell_volume                     746.97(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    3215
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      27.0

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.312
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    4.246
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.27
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7773
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.760
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3215
_reflns_number_gt                2285
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0592
_refine_ls_wR_factor_gt          0.0563
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
C10 C 0.6546(5) 0.5639(5) 0.5998(3) 0.0509(9) Uani 1 1 d . . . . .
C3 C 0.6838(5) 0.2446(4) 0.0442(3) 0.0430(8) Uani 1 1 d . . . . .
C7 C 1.0872(6) 0.2225(5) -0.0083(4) 0.0579(10) Uani 1 1 d . . . . .
C12 C 0.9114(5) 0.8317(4) 0.4220(3) 0.0449(9) Uani 1 1 d . . . . .
C11 C 1.0375(5) 0.8672(5) 0.5368(3) 0.0484(9) Uani 1 1 d . . . . .
C13 C 0.8767(5) 0.9683(5) 0.3876(3) 0.0497(9) Uani 1 1 d . . . . .
N1 N 1.2162(6) 0.1997(5) 0.0050(4) 0.0804(12) Uani 1 1 d . . . . .
N2 N 0.6043(5) 0.2209(5) 0.1302(3) 0.0559(9) Uani 1 1 d . . . . .
F1 F 1.0773(4) 0.7428(3) 0.5785(2) 0.0737(7) Uani 1 1 d . . . . .
F2 F 0.7566(4) 0.9411(3) 0.2750(2) 0.0774(8) Uani 1 1 d . . . . .
F3 F 0.3154(4) 0.7027(3) 0.4323(2) 0.0768(7) Uani 1 1 d . . . . .
F4 F 0.8060(3) 0.6219(3) 0.6977(2) 0.0798(8) Uani 1 1 d . . . . .
H1N H 0.621(8) 0.149(7) 0.160(5) 0.120 Uiso 1 1 d . U . . .
H2N H 0.489(8) 0.201(7) 0.094(5) 0.120 Uiso 1 1 d . U . . .
C8 C 0.4089(6) 0.6043(5) 0.4673(3) 0.0516(10) Uani 1 1 d . . . . .
C9 C 0.5650(5) 0.6723(4) 0.5690(3) 0.0498(9) Uani 1 1 d . . . . .
C2 C 0.8402(5) 0.2171(4) 0.0561(3) 0.0435(9) Uani 1 1 d . . . . .
H2 H 0.8917 0.1759 0.1197 0.052 Uiso 1 1 calc R U . . .
C1 C 0.9209(4) 0.2507(4) -0.0266(3) 0.0420(8) Uani 1 1 d . . . . .
C6 C 0.8495(5) 0.3143(4) -0.1206(3) 0.0498(9) Uani 1 1 d . . . . .
H6 H 0.9061 0.3393 -0.1747 0.060 Uiso 1 1 calc R U . . .
C5 C 0.6930(5) 0.3395(5) -0.1320(3) 0.0531(10) Uani 1 1 d . . . . .
H5 H 0.6417 0.3807 -0.1957 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6107(5) 0.3059(5) -0.0525(3) 0.0484(9) Uani 1 1 d . . . . .
H4 H 0.5040 0.3240 -0.0627 0.058 Uiso 1 1 calc R U . . .
I1 I 0.78271(4) 0.58196(3) 0.30642(2) 0.05193(10) Uani 1 1 d . . . . .
I2 I 0.65880(5) 0.92445(3) 0.67279(3) 0.07468(12) 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
C10 F4 1.332(4) . ?
C10 C8 1.367(5) 2_666 ?
C10 C9 1.375(5) . ?
C3 C2 1.372(5) . ?
C3 C4 1.392(5) . ?
C3 N2 1.396(5) . ?
C7 N1 1.127(5) . ?
C7 C1 1.447(6) . ?
C12 C11 1.371(5) . ?
C12 C13 1.374(5) . ?
C12 I1 2.081(3) . ?
C11 F1 1.328(4) . ?
C11 C13 1.369(5) 2_776 ?
C13 F2 1.345(4) . ?
C13 C11 1.369(5) 2_776 ?
F3 C8 1.337(4) . ?
C8 C10 1.367(5) 2_666 ?
C8 C9 1.376(5) . ?
C9 I2 2.061(3) . ?
C2 C1 1.382(5) . ?
C1 C6 1.376(5) . ?
C6 C5 1.366(5) . ?
C5 C4 1.358(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
F4 C10 C8 118.5(4) . 2_666 ?
F4 C10 C9 120.0(3) . . ?
C8 C10 C9 121.5(4) 2_666 . ?
C2 C3 C4 118.3(3) . . ?
C2 C3 N2 121.2(3) . . ?
C4 C3 N2 120.4(3) . . ?
N1 C7 C1 179.5(5) . . ?
C11 C12 C13 116.8(3) . . ?
C11 C12 I1 120.9(3) . . ?
C13 C12 I1 122.3(3) . . ?
F1 C11 C13 118.3(3) . 2_776 ?
F1 C11 C12 120.9(3) . . ?
C13 C11 C12 120.8(3) 2_776 . ?
F2 C13 C11 118.3(3) . 2_776 ?
F2 C13 C12 119.3(3) . . ?
C11 C13 C12 122.4(3) 2_776 . ?
F3 C8 C10 118.5(4) . 2_666 ?
F3 C8 C9 120.2(3) . . ?
C10 C8 C9 121.4(4) 2_666 . ?
C10 C9 C8 117.1(3) . . ?
C10 C9 I2 121.3(3) . . ?
C8 C9 I2 121.6(3) . . ?
C3 C2 C1 119.9(3) . . ?
C6 C1 C2 121.5(3) . . ?
C6 C1 C7 120.9(4) . . ?
C2 C1 C7 117.5(3) . . ?
C5 C6 C1 118.0(4) . . ?
C4 C5 C6 121.5(3) . . ?
C5 C4 C3 120.9(3) . . ?

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_3ap_tfib
_database_code_depnum_ccdc_archive 'CCDC 1494269'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C5 H6 N2 '
_chemical_formula_sum            'C11 H6 F4 I2 N2'
_chemical_formula_weight         495.98

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.5682(17)
_cell_length_b                   13.372(3)
_cell_length_c                   14.198(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.4570(10)
_cell_angle_gamma                90
_cell_volume                     1384.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    2281
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.379
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    4.574
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_T_max  0.61
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6550
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.816
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             2281
_reflns_number_gt                1553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0865P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2281
_refine_ls_number_parameters     178
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.921
_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_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
I1 I 0.56800(7) 0.24853(4) 0.45821(4) 0.0583(2) Uani 1 1 d . . . . .
I2 I 0.64128(12) 0.02607(6) 0.91113(5) 0.0875(3) Uani 1 1 d . . . . .
F1 F 0.6852(7) 0.0311(4) 0.5414(4) 0.0664(13) Uani 1 1 d . . . . .
F3 F 0.4906(7) 0.3298(4) 0.6587(4) 0.0709(14) Uani 1 1 d . . . . .
F2 F 0.7101(7) -0.0543(4) 0.7142(4) 0.0765(15) Uani 1 1 d . . . . .
F4 F 0.5233(8) 0.2447(4) 0.8304(4) 0.0763(16) Uani 1 1 d . . . . .
C7 C 0.6414(9) 0.0850(6) 0.6118(5) 0.0494(19) Uani 1 1 d . . . . .
N1 N 0.5673(11) 0.3268(7) 0.2746(6) 0.070(2) Uani 1 1 d . . . . .
C8 C 0.6565(11) 0.0413(6) 0.7011(7) 0.056(2) Uani 1 1 d . . . . .
C6 C 0.5874(9) 0.1818(6) 0.5951(5) 0.0445(17) Uani 1 1 d . . . . .
C10 C 0.5623(11) 0.1909(6) 0.7595(6) 0.054(2) Uani 1 1 d . . . . .
C11 C 0.5483(11) 0.2343(6) 0.6713(6) 0.0493(19) Uani 1 1 d . . . . .
C9 C 0.6190(11) 0.0925(7) 0.7768(6) 0.056(2) Uani 1 1 d . . . . .
C4 C 0.5808(13) 0.2891(9) 0.1113(9) 0.079(3) Uani 1 1 d . . . . .
H4 H 0.5717 0.2420 0.0621 0.095 Uiso 1 1 calc R U . . .
C3 C 0.6236(12) 0.3814(8) 0.1002(7) 0.066(2) Uani 1 1 d . . . . .
H3 H 0.6441 0.3996 0.0408 0.079 Uiso 1 1 calc R U . . .
C2 C 0.6404(12) 0.4531(7) 0.1695(9) 0.075(3) Uani 1 1 d . . . . .
C1 C 0.6068(12) 0.4196(8) 0.2614(7) 0.071(3) Uani 1 1 d . . . . .
H1 H 0.6138 0.4656 0.3114 0.086 Uiso 1 1 calc R U . . .
C5 C 0.5498(14) 0.2645(9) 0.1989(9) 0.080(3) Uani 1 1 d . . . . .
H5 H 0.5137 0.1992 0.2065 0.096 Uiso 1 1 calc R U . . .
N2 N 0.6920(19) 0.5498(9) 0.1671(11) 0.118(4) Uani 1 1 d D . . . .
H1N H 0.64(2) 0.571(13) 0.106(4) 0.178 Uiso 1 1 d D U . . .
H2N H 0.66(2) 0.584(11) 0.215(7) 0.178 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C6 2.108(7) . ?
I2 C9 2.069(8) . ?
F1 C7 1.343(9) . ?
F3 C11 1.346(9) . ?
F2 C8 1.339(9) . ?
F4 C10 1.334(9) . ?
C7 C6 1.359(11) . ?
C7 C8 1.373(12) . ?
N1 C1 1.302(13) . ?
N1 C5 1.339(14) . ?
C8 C9 1.366(12) . ?
C6 C11 1.387(11) . ?
C10 C11 1.358(12) . ?
C10 C9 1.385(12) . ?
C4 C3 1.296(15) . ?
C4 C5 1.365(16) . ?
C4 H4 0.9300 . ?
C3 C2 1.355(14) . ?
C3 H3 0.9300 . ?
C2 N2 1.354(15) . ?
C2 C1 1.464(14) . ?
C1 H1 0.9300 . ?
C5 H5 0.9300 . ?
N2 H1N 0.89(2) . ?
N2 H2N 0.89(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
F1 C7 C6 120.2(7) . . ?
F1 C7 C8 118.9(7) . . ?
C6 C7 C8 120.9(7) . . ?
C1 N1 C5 117.1(8) . . ?
F2 C8 C9 119.2(8) . . ?
F2 C8 C7 118.8(8) . . ?
C9 C8 C7 122.0(8) . . ?
C7 C6 C11 117.6(7) . . ?
C7 C6 I1 120.5(5) . . ?
C11 C6 I1 121.9(6) . . ?
F4 C10 C11 119.1(8) . . ?
F4 C10 C9 119.9(7) . . ?
C11 C10 C9 121.0(7) . . ?
F3 C11 C10 118.1(7) . . ?
F3 C11 C6 120.4(7) . . ?
C10 C11 C6 121.5(7) . . ?
C8 C9 C10 117.1(8) . . ?
C8 C9 I2 121.8(7) . . ?
C10 C9 I2 121.1(6) . . ?
C3 C4 C5 116.7(12) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 H4 121.7 . . ?
C4 C3 C2 124.3(10) . . ?
C4 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
N2 C2 C3 129.0(11) . . ?
N2 C2 C1 115.7(12) . . ?
C3 C2 C1 115.2(9) . . ?
N1 C1 C2 121.4(10) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
N1 C5 C4 125.2(11) . . ?
N1 C5 H5 117.4 . . ?
C4 C5 H5 117.4 . . ?
C2 N2 H1N 107(10) . . ?
C2 N2 H2N 110(10) . . ?
H1N N2 H2N 116(6) . . ?

_refine_diff_density_max         0.993
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.186

####################################################################### 
# 
# 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_4aap2_tfib
_database_code_depnum_ccdc_archive 'CCDC 1494270'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C8 H9 N O)'
_chemical_formula_sum            'C22 H18 F4 I2 N2 O2'
_chemical_formula_weight         672.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4740 1.8120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1553(3)
_cell_length_b                   9.6907(6)
_cell_length_c                   10.8382(5)
_cell_angle_alpha                113.014(5)
_cell_angle_beta                 96.686(4)
_cell_angle_gamma                104.202(5)
_cell_volume                     560.28(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    295
_cell_measurement_reflns_used    2381
_cell_measurement_theta_min      4.0
_cell_measurement_theta_max      27.0

_exptl_crystal_description       plate
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.992
_exptl_crystal_F_000             322
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    2.862
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7170
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.038
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2381
_reflns_number_gt                2168
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2381
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0492
_refine_ls_wR_factor_gt          0.0487
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002

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
F2 F -0.2507(3) 0.45916(19) 0.17966(17) 0.0558(4) Uani 1 1 d . . . . .
F1 F 0.3145(3) 0.34962(18) -0.06777(17) 0.0557(4) Uani 1 1 d . . . . .
C11 C -0.1238(4) 0.4781(2) 0.0908(2) 0.0359(4) Uani 1 1 d . . . . .
C10 C 0.0366(4) 0.4005(2) 0.0608(2) 0.0342(4) Uani 1 1 d . . . . .
C9 C 0.1587(4) 0.4237(2) -0.0326(2) 0.0360(4) Uani 1 1 d . . . . .
N1 N 0.3067(6) 0.6077(3) 0.5599(3) 0.0610(6) Uani 1 1 d . . . . .
O1 O 0.1475(4) 1.0309(3) 0.2583(2) 0.0641(5) Uani 1 1 d . . . . .
C7 C 0.2905(4) 0.9633(3) 0.2527(2) 0.0422(5) Uani 1 1 d . . . . .
C8 C 0.4663(5) 0.9798(3) 0.1706(3) 0.0538(6) Uani 1 1 d . . . . .
H8A H 0.4473 1.0517 0.1326 0.081 Uiso 1 1 calc R U . . .
H8B H 0.4461 0.8784 0.0971 0.081 Uiso 1 1 calc R U . . .
H8C H 0.6183 1.0200 0.2294 0.081 Uiso 1 1 calc R U . . .
H1N H 0.202(6) 0.620(4) 0.611(3) 0.062(9) Uiso 1 1 d . . . . .
H2N H 0.446(8) 0.626(6) 0.604(5) 0.120(18) Uiso 1 1 d . . . . .
I1 I 0.08904(3) 0.24901(2) 0.14626(2) 0.04367(7) Uani 1 1 d . . . . .
C1 C 0.2941(4) 0.8641(2) 0.3268(2) 0.0341(4) Uani 1 1 d . . . . .
C6 C 0.4638(4) 0.7952(3) 0.3331(2) 0.0401(5) Uani 1 1 d . . . . .
H6 H 0.5772 0.8061 0.2847 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1242(4) 0.8444(3) 0.3995(2) 0.0421(5) Uani 1 1 d . . . . .
H2 H 0.0075 0.8892 0.3961 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3024(4) 0.6934(3) 0.4836(2) 0.0414(5) Uani 1 1 d . . . . .
C3 C 0.1274(4) 0.7596(3) 0.4761(3) 0.0447(5) Uani 1 1 d . . . . .
H3 H 0.0123 0.7467 0.5229 0.054 Uiso 1 1 calc R U . . .
C5 C 0.4684(4) 0.7107(3) 0.4094(3) 0.0465(5) Uani 1 1 d . . . . .
H5 H 0.5839 0.6647 0.4115 0.056 Uiso 1 1 calc R U . . .


_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
F2 C11 1.347(2) . ?
F1 C9 1.337(2) . ?
C11 C10 1.376(3) . ?
C11 C9 1.374(3) 2_565 ?
C10 C9 1.383(3) . ?
C10 I1 2.084(2) . ?
C9 C11 1.374(3) 2_565 ?
N1 C4 1.384(3) . ?
O1 C7 1.213(3) . ?
C7 C1 1.475(3) . ?
C7 C8 1.497(3) . ?
C1 C6 1.380(3) . ?
C1 C2 1.401(3) . ?
C6 C5 1.376(3) . ?
C2 C3 1.379(3) . ?
C4 C5 1.390(3) . ?
C4 C3 1.392(4) . ?

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
F2 C11 C10 120.03(19) . . ?
F2 C11 C9 118.30(19) . 2_565 ?
C10 C11 C9 121.67(19) . 2_565 ?
C11 C10 C9 116.94(19) . . ?
C11 C10 I1 122.17(15) . . ?
C9 C10 I1 120.86(15) . . ?
F1 C9 C11 118.80(19) . 2_565 ?
F1 C9 C10 119.82(19) . . ?
C11 C9 C10 121.38(19) 2_565 . ?
O1 C7 C1 120.7(2) . . ?
O1 C7 C8 120.3(2) . . ?
C1 C7 C8 119.1(2) . . ?
C6 C1 C2 118.1(2) . . ?
C6 C1 C7 123.0(2) . . ?
C2 C1 C7 118.9(2) . . ?
C5 C6 C1 121.2(2) . . ?
C3 C2 C1 121.0(2) . . ?
N1 C4 C5 120.7(2) . . ?
N1 C4 C3 120.6(2) . . ?
C5 C4 C3 118.7(2) . . ?
C2 C3 C4 120.2(2) . . ?
C6 C5 C4 120.8(2) . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_4ab2_tfib
_database_code_depnum_ccdc_archive 'CCDC 1494271'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H11 N O), C6 F4 I2'
_chemical_formula_sum            'C32 H22 F4 I2 N2 O2'
_chemical_formula_weight         796.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.4300(7)
_cell_length_b                   5.6597(4)
_cell_length_c                   31.140(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.781(7)
_cell_angle_gamma                90
_cell_volume                     1480.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    3213
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      27.0

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.736
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    2.182
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14877
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.832
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3213
_reflns_number_gt                1831
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3213
_refine_ls_number_parameters     196
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_restrained_S_all      0.898
_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_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
I1 I 1.03305(4) 0.16170(6) 0.40793(2) 0.07056(17) Uani 1 1 d . . . . .
F1 F 0.8391(3) 0.6300(5) 0.42515(9) 0.0722(8) Uani 1 1 d . . . . .
F2 F 1.1884(4) 0.1131(5) 0.50425(10) 0.0782(8) Uani 1 1 d . . . . .
O1 O 0.5383(4) 0.8269(7) 0.31389(12) 0.0832(11) Uani 1 1 d . . . . .
N1 N -0.1961(5) 1.0714(9) 0.27884(16) 0.0739(12) Uani 1 1 d D . . . .
C4 C -0.0466(5) 1.0019(8) 0.29299(14) 0.0526(11) Uani 1 1 d . . . . .
C2 C 0.1279(5) 0.7265(8) 0.33165(14) 0.0527(11) Uani 1 1 d . . . . .
H2 H 0.1411 0.5912 0.3485 0.063 Uiso 1 1 calc R U . . .
C1 C 0.2626(5) 0.8475(8) 0.32059(14) 0.0498(11) Uani 1 1 d . . . . .
C3 C -0.0228(5) 0.7995(8) 0.31859(14) 0.0537(12) Uani 1 1 d . . . . .
H3 H -0.1099 0.7146 0.3267 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2383(5) 1.0462(9) 0.29511(14) 0.0544(11) Uani 1 1 d . . . . .
H6 H 0.3257 1.1289 0.2866 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4248(6) 0.7617(9) 0.33335(16) 0.0596(13) Uani 1 1 d . . . . .
C5 C 0.0889(6) 1.1235(8) 0.28212(14) 0.0568(12) Uani 1 1 d . . . . .
H5 H 0.0767 1.2604 0.2656 0.068 Uiso 1 1 calc R U . . .
C15 C 0.9197(5) 0.5612(8) 0.46186(15) 0.0525(11) Uani 1 1 d . . . . .
C14 C 1.0139(5) 0.3652(8) 0.46281(15) 0.0508(11) Uani 1 1 d . . . . .
C13 C 0.3947(6) 0.6346(9) 0.40995(17) 0.0612(12) Uani 1 1 d . . . . .
H13 H 0.3337 0.7688 0.4136 0.073 Uiso 1 1 calc R U . . .
C16 C 1.0929(5) 0.3050(8) 0.50143(17) 0.0569(12) Uani 1 1 d . . . . .
C8 C 0.4521(5) 0.5896(8) 0.36977(18) 0.0605(13) Uani 1 1 d . . . . .
C9 C 0.5435(6) 0.3928(11) 0.3650(2) 0.0842(18) Uani 1 1 d . . . . .
H9 H 0.5858 0.3633 0.3389 0.101 Uiso 1 1 calc R U . . .
C11 C 0.5155(9) 0.2864(14) 0.4380(3) 0.111(3) Uani 1 1 d . . . . .
H11 H 0.5366 0.1833 0.4610 0.133 Uiso 1 1 calc R U . . .
C10 C 0.5728(8) 0.2378(12) 0.3991(4) 0.108(3) Uani 1 1 d . . . . .
H10 H 0.6314 0.1010 0.3956 0.130 Uiso 1 1 calc R U . . .
C12 C 0.4267(7) 0.4866(13) 0.4432(2) 0.0898(19) Uani 1 1 d . . . . .
H12 H 0.3889 0.5194 0.4698 0.108 Uiso 1 1 calc R U . . .
H1N H -0.273(5) 0.999(10) 0.291(2) 0.135 Uiso 1 1 d D U . . .
H2N H -0.217(7) 1.200(8) 0.264(2) 0.135 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C14 2.078(4) . ?
F1 C15 1.338(5) . ?
F2 C16 1.350(5) . ?
O1 C7 1.231(5) . ?
N1 C4 1.358(6) . ?
N1 H1N 0.883(19) . ?
N1 H2N 0.868(19) . ?
C4 C5 1.399(6) . ?
C4 C3 1.401(6) . ?
C2 C3 1.365(6) . ?
C2 C1 1.394(6) . ?
C2 H2 0.9300 . ?
C1 C6 1.381(6) . ?
C1 C7 1.474(7) . ?
C3 H3 0.9300 . ?
C6 C5 1.362(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.498(7) . ?
C5 H5 0.9300 . ?
C15 C14 1.363(6) . ?
C15 C16 1.383(7) 3_766 ?
C14 C16 1.368(7) . ?
C13 C12 1.342(7) . ?
C13 C8 1.402(7) . ?
C13 H13 0.9300 . ?
C16 C15 1.383(7) 3_766 ?
C8 C9 1.369(7) . ?
C9 C10 1.383(11) . ?
C9 H9 0.9300 . ?
C11 C10 1.368(11) . ?
C11 C12 1.375(10) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?

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
C4 N1 H1N 115(4) . . ?
C4 N1 H2N 124(4) . . ?
H1N N1 H2N 120(5) . . ?
N1 C4 C5 122.2(4) . . ?
N1 C4 C3 120.4(4) . . ?
C5 C4 C3 117.3(4) . . ?
C3 C2 C1 122.3(4) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C6 C1 C2 117.2(4) . . ?
C6 C1 C7 120.9(4) . . ?
C2 C1 C7 121.9(4) . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C6 C1 121.4(4) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C7 C1 120.7(5) . . ?
O1 C7 C8 119.4(5) . . ?
C1 C7 C8 120.0(4) . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
F1 C15 C14 120.6(4) . . ?
F1 C15 C16 118.6(4) . 3_766 ?
C14 C15 C16 120.8(4) . 3_766 ?
C15 C14 C16 117.5(4) . . ?
C15 C14 I1 121.2(4) . . ?
C16 C14 I1 121.3(3) . . ?
C12 C13 C8 120.9(5) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
F2 C16 C14 120.1(4) . . ?
F2 C16 C15 118.2(5) . 3_766 ?
C14 C16 C15 121.7(4) . 3_766 ?
C9 C8 C13 118.9(6) . . ?
C9 C8 C7 120.0(5) . . ?
C13 C8 C7 121.0(4) . . ?
C8 C9 C10 120.0(7) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C10 C11 C12 120.5(7) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C10 C9 119.8(7) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C13 C12 C11 119.9(7) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?

_refine_diff_density_max         0.621
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_4noa2_tfib
_database_code_depnum_ccdc_archive 'CCDC 1494272'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C6 H6 N2 O2)'
_chemical_formula_sum            'C18 H12 F4 I2 N4 O4'
_chemical_formula_weight         678.12

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4529(6)
_cell_length_b                   10.6844(8)
_cell_length_c                   12.1719(17)
_cell_angle_alpha                96.727(2)
_cell_angle_beta                 112.766(4)
_cell_angle_gamma                103.570(6)
_cell_volume                     1071.86(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    3771
_cell_measurement_theta_min      3.7
_cell_measurement_theta_max      25.0

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.101
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    3.002
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.31
_exptl_absorpt_correction_T_max  0.77
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11446
_diffrn_reflns_av_unetI/netI     0.1402
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.667
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3771
_reflns_number_gt                1750
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0727P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3771
_refine_ls_number_parameters     301
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   0.818
_refine_ls_restrained_S_all      0.817
_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_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 0.1356(12) 0.1572(12) 0.8497(10) 0.054(3) Uani 1 1 d D . . . .
C2 C 0.0466(13) 0.1825(12) 0.9138(11) 0.055(3) Uani 1 1 d . . . . .
H2 H 0.0282 0.1289 0.9648 0.066 Uiso 1 1 calc R U . . .
C3 C -0.0113(13) 0.2848(12) 0.9005(11) 0.054(3) Uani 1 1 d . . . . .
H3 H -0.0722 0.3016 0.9417 0.064 Uiso 1 1 calc R U . . .
C4 C 0.0181(12) 0.3683(12) 0.8247(11) 0.052(3) Uani 1 1 d D . . . .
C5 C 0.1065(13) 0.3402(13) 0.7621(11) 0.056(3) Uani 1 1 d . . . . .
H5 H 0.1262 0.3938 0.7114 0.067 Uiso 1 1 calc R U . . .
C6 C 0.1621(12) 0.2396(12) 0.7738(10) 0.055(3) Uani 1 1 d D . . . .
H6 H 0.2207 0.2222 0.7308 0.066 Uiso 1 1 calc R U . . .
C7 C 0.8422(12) 0.8527(11) 0.6406(10) 0.048(3) Uani 1 1 d . . . . .
C8 C 0.8061(13) 0.9572(12) 0.5845(11) 0.057(3) Uani 1 1 d . . . . .
H8 H 0.8472 0.9808 0.5292 0.069 Uiso 1 1 calc R U . . .
C9 C 0.7124(13) 1.0231(11) 0.6103(11) 0.053(3) Uani 1 1 d . . . . .
H9 H 0.6914 1.0923 0.5735 0.063 Uiso 1 1 calc R U . . .
C10 C 0.6469(13) 0.9882(11) 0.6915(10) 0.046(3) Uani 1 1 d . . . . .
C11 C 0.6867(13) 0.8854(12) 0.7489(10) 0.053(3) Uani 1 1 d . . . . .
H11 H 0.6469 0.8633 0.8052 0.063 Uiso 1 1 calc R U . . .
C12 C 0.7821(13) 0.8169(11) 0.7247(10) 0.053(3) Uani 1 1 d . . . . .
H12 H 0.8057 0.7492 0.7630 0.064 Uiso 1 1 calc R U . . .
C13 C 0.5379(13) 0.5682(12) 0.9183(10) 0.047(3) Uani 1 1 d . . . . .
C14 C 0.4487(12) 0.6094(11) 0.9752(11) 0.049(3) Uani 1 1 d . . . . .
C15 C 0.5855(12) 0.4618(12) 0.9434(11) 0.054(3) Uani 1 1 d . . . . .
C16 C 0.3906(11) 0.5546(12) 0.5207(10) 0.046(3) Uani 1 1 d . . . . .
C17 C 0.4280(12) 0.4520(11) 0.5728(10) 0.044(3) Uani 1 1 d . . . . .
C18 C 0.5333(12) 0.3976(10) 0.5506(10) 0.044(3) Uani 1 1 d . . . . .
N1 N 0.1993(12) 0.0414(11) 0.8612(12) 0.065(3) Uani 1 1 d . . . . .
N2 N -0.0410(12) 0.4735(11) 0.8146(10) 0.074(3) Uani 1 1 d D . . . .
H1N H -0.145(4) 0.455(4) 0.765(9) 0.111 Uiso 1 1 d D U . . .
H2N H 0.016(8) 0.543(5) 0.800(11) 0.111 Uiso 1 1 d D U . . .
N3 N 0.9431(11) 0.7820(11) 0.6129(11) 0.060(3) Uani 1 1 d . . . . .
N4 N 0.5506(14) 1.0487(13) 0.7167(12) 0.075(3) Uani 1 1 d D . . . .
H3N H 0.497(14) 1.015(13) 0.758(11) 0.113 Uiso 1 1 d D U . . .
H4N H 0.519(15) 1.107(11) 0.677(12) 0.113 Uiso 1 1 d D U . . .
O1 O 0.1807(12) -0.0224(11) 0.9366(10) 0.091(3) Uani 1 1 d . . . . .
O2 O 0.2685(11) 0.0150(11) 0.7987(10) 0.096(3) Uani 1 1 d . . . . .
O3 O 0.9700(11) 0.6942(9) 0.6665(10) 0.088(3) Uani 1 1 d . . . . .
O4 O 0.9988(12) 0.8192(11) 0.5418(10) 0.089(3) Uani 1 1 d . . . . .
F1 F 0.5767(8) 0.6299(7) 0.8419(6) 0.0655(19) Uani 1 1 d . . . . .
F2 F 0.6723(8) 0.4246(7) 0.8866(6) 0.070(2) Uani 1 1 d . . . . .
F3 F 0.3555(8) 0.4008(7) 0.6401(6) 0.0667(19) Uani 1 1 d . . . . .
F4 F 0.5637(8) 0.2947(7) 0.6006(6) 0.069(2) Uani 1 1 d . . . . .
I1 I 0.36227(9) 0.77119(8) 0.93807(8) 0.0588(3) Uani 1 1 d . . . . .
I2 I 0.23042(8) 0.64358(8) 0.55358(7) 0.0584(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
C1 C2 1.398(16) . ?
C1 C6 1.399(9) . ?
C1 N1 1.496(15) . ?
C2 C3 1.332(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(16) . ?
C3 H3 0.9300 . ?
C4 N2 1.365(15) . ?
C4 C5 1.388(16) . ?
C5 C6 1.302(16) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.399(15) . ?
C7 C8 1.416(16) . ?
C7 N3 1.456(14) . ?
C8 C9 1.354(15) . ?
C8 H8 0.9300 . ?
C9 C10 1.397(15) . ?
C9 H9 0.9300 . ?
C10 N4 1.337(14) . ?
C10 C11 1.415(15) . ?
C11 C12 1.378(15) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 F1 1.315(12) . ?
C13 C15 1.343(15) . ?
C13 C14 1.392(16) . ?
C14 C15 1.404(16) 2_667 ?
C14 I1 2.103(11) . ?
C15 F2 1.356(13) . ?
C15 C14 1.404(16) 2_667 ?
C16 C17 1.379(15) . ?
C16 C18 1.396(15) 2_666 ?
C16 I2 2.100(10) . ?
C17 F3 1.343(12) . ?
C17 C18 1.358(14) . ?
C18 F4 1.354(12) . ?
C18 C16 1.396(15) 2_666 ?
N1 O2 1.228(14) . ?
N1 O1 1.246(14) . ?
N2 H1N 0.89(2) . ?
N2 H2N 0.89(2) . ?
N3 O3 1.223(13) . ?
N3 O4 1.233(13) . ?
N4 H3N 0.89(2) . ?
N4 H4N 0.88(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
C2 C1 C6 119.5(11) . . ?
C2 C1 N1 119.9(12) . . ?
C6 C1 N1 120.6(12) . . ?
C3 C2 C1 118.9(12) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.1(11) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
N2 C4 C5 121.8(12) . . ?
N2 C4 C3 119.6(12) . . ?
C5 C4 C3 118.7(12) . . ?
C6 C5 C4 120.6(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 121.4(11) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C12 C7 C8 120.1(11) . . ?
C12 C7 N3 119.0(11) . . ?
C8 C7 N3 120.9(12) . . ?
C9 C8 C7 120.9(11) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.7(11) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
N4 C10 C9 122.4(11) . . ?
N4 C10 C11 119.9(12) . . ?
C9 C10 C11 117.8(10) . . ?
C12 C11 C10 122.8(11) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 C7 117.7(11) . . ?
C11 C12 H12 121.1 . . ?
C7 C12 H12 121.1 . . ?
F1 C13 C15 119.5(11) . . ?
F1 C13 C14 122.3(11) . . ?
C15 C13 C14 118.2(12) . . ?
C13 C14 C15 118.3(11) . 2_667 ?
C13 C14 I1 121.2(9) . . ?
C15 C14 I1 120.5(9) 2_667 . ?
C13 C15 F2 116.6(11) . . ?
C13 C15 C14 123.5(11) . 2_667 ?
F2 C15 C14 119.9(11) . 2_667 ?
C17 C16 C18 118.6(9) . 2_666 ?
C17 C16 I2 121.1(9) . . ?
C18 C16 I2 120.3(9) 2_666 . ?
F3 C17 C18 119.6(10) . . ?
F3 C17 C16 120.8(9) . . ?
C18 C17 C16 119.6(11) . . ?
F4 C18 C17 117.8(10) . . ?
F4 C18 C16 120.3(10) . 2_666 ?
C17 C18 C16 121.8(10) . 2_666 ?
O2 N1 O1 123.4(13) . . ?
O2 N1 C1 119.5(13) . . ?
O1 N1 C1 117.2(12) . . ?
C4 N2 H1N 116(3) . . ?
C4 N2 H2N 116(3) . . ?
H1N N2 H2N 110(5) . . ?
O3 N3 O4 125.9(11) . . ?
O3 N3 C7 116.7(12) . . ?
O4 N3 C7 117.4(12) . . ?
C10 N4 H3N 120(9) . . ?
C10 N4 H4N 120(9) . . ?
H3N N4 H4N 118(6) . . ?

_refine_diff_density_max         0.795
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.244

####################################################################### 
# 
# 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_5a2mp2_tfib
_database_code_depnum_ccdc_archive 'CCDC 1494273'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C6 H8 N2 O)'
_chemical_formula_sum            'C18 H16 F4 I2 N4 O2'
_chemical_formula_weight         650.15

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0259(3)
_cell_length_b                   8.6495(4)
_cell_length_c                   20.3527(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.507(5)
_cell_angle_gamma                90
_cell_volume                     1058.82(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_measurement_reflns_used    2077
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      26.0

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.039
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    3.027
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_T_max  0.62
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6366
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.822
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2077
_reflns_number_gt                1433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0169(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2077
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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_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
C6 C 0.7291(8) 0.4912(6) 0.4330(3) 0.0664(14) Uani 1 1 d . . . . .
H1C H 0.7209 0.4405 0.4748 0.100 Uiso 1 1 calc R U . . .
H2C H 0.6035 0.5586 0.4257 0.100 Uiso 1 1 calc R U . . .
H3C H 0.7283 0.4152 0.3987 0.100 Uiso 1 1 calc R U . . .
I1 I 0.28097(5) 0.74331(3) 0.11745(2) 0.05904(19) Uani 1 1 d . . . . .
C2 C 1.1709(8) 0.7367(5) 0.3786(2) 0.0515(12) Uani 1 1 d . . . . .
H2 H 1.2737 0.7271 0.4144 0.062 Uiso 1 1 calc R U . . .
N1 N 0.8205(6) 0.6637(5) 0.3274(2) 0.0544(9) Uani 1 1 d . . . . .
C5 C 0.8677(9) 0.7561(5) 0.2759(2) 0.0572(12) Uani 1 1 d . . . . .
H5 H 0.7653 0.7598 0.2398 0.069 Uiso 1 1 calc R U . . .
F2 F 0.1008(4) 0.6366(3) -0.02726(14) 0.0681(8) Uani 1 1 d . . . . .
C1 C 0.9691(7) 0.6599(5) 0.3773(2) 0.0461(10) Uani 1 1 d . . . . .
F1 F 0.7344(4) 0.5506(4) 0.11556(15) 0.0713(9) Uani 1 1 d . . . . .
C8 C 0.4132(7) 0.5996(4) 0.0467(2) 0.0474(11) Uani 1 1 d . . . . .
N2 N 1.0935(8) 0.9397(5) 0.2199(2) 0.0636(12) Uani 1 1 d . . . . .
H1N H 1.187(10) 1.016(6) 0.229(3) 0.095 Uiso 1 1 d . U . . .
H2N H 0.970(9) 0.994(6) 0.208(3) 0.095 Uiso 1 1 d . U . . .
C3 C 1.2153(7) 0.8282(5) 0.3254(2) 0.0534(12) Uani 1 1 d . . . . .
H3 H 1.3511 0.8788 0.3242 0.064 Uiso 1 1 calc R U . . .
C4 C 1.0568(7) 0.8439(5) 0.2739(2) 0.0494(11) Uani 1 1 d . . . . .
O1 O 0.9292(5) 0.5794(4) 0.43306(16) 0.0591(8) Uani 1 1 d . . . . .
C7 C 0.6161(7) 0.5268(5) 0.0583(2) 0.0507(11) Uani 1 1 d . . . . .
C9 C 0.3010(7) 0.5696(5) -0.0125(3) 0.0503(12) 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
C6 O1 1.427(6) . ?
I1 C8 2.096(4) . ?
C2 C3 1.381(7) . ?
C2 C1 1.385(6) . ?
N1 C1 1.313(5) . ?
N1 C5 1.362(6) . ?
C5 C4 1.372(6) . ?
F2 C9 1.356(5) . ?
C1 O1 1.365(5) . ?
F1 C7 1.345(5) . ?
C8 C9 1.370(6) . ?
C8 C7 1.383(6) . ?
N2 C4 1.404(6) . ?
C3 C4 1.381(6) . ?
C7 C9 1.368(7) 3_665 ?
C9 C7 1.367(7) 3_665 ?

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
C3 C2 C1 118.1(4) . . ?
C1 N1 C5 116.5(4) . . ?
N1 C5 C4 124.1(4) . . ?
N1 C1 O1 120.6(4) . . ?
N1 C1 C2 124.0(4) . . ?
O1 C1 C2 115.3(4) . . ?
C9 C8 C7 116.5(4) . . ?
C9 C8 I1 121.9(3) . . ?
C7 C8 I1 121.5(4) . . ?
C2 C3 C4 119.6(4) . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 N2 121.4(5) . . ?
C3 C4 N2 121.2(4) . . ?
C1 O1 C6 117.7(4) . . ?
F1 C7 C9 119.2(4) . 3_665 ?
F1 C7 C8 119.6(4) . . ?
C9 C7 C8 121.2(4) 3_665 . ?
F2 C9 C7 117.8(4) . 3_665 ?
F2 C9 C8 119.9(4) . . ?
C7 C9 C8 122.3(4) 3_665 . ?

_refine_diff_density_max         0.793
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.425

