# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_R_P21
_database_code_depnum_ccdc_archive 'CCDC 1995556'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-18 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 H13 F N, I'
_chemical_formula_sum            'C6 H13 F I N'
_chemical_formula_weight         245.07

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.9613(3)
_cell_length_b                   7.6228(3)
_cell_length_c                   10.1630(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.627(4)
_cell_angle_gamma                90
_cell_volume                     444.75(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3722
_cell_measurement_theta_min      2.6700
_cell_measurement_theta_max      30.2280

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    3.543
_shelx_estimated_absorpt_T_min   0.510
_shelx_estimated_absorpt_T_max   0.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.463
_exptl_absorpt_correction_T_max  0.475
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3477
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_av_R_equivalents  0.0093
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.388
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1748
_reflns_number_gt                1626
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+0.4091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1748
_refine_ls_number_parameters     85
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0477
_refine_ls_wR_factor_gt          0.0476
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.007

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 0.96634(4) 0.12132(18) 0.67638(3) 0.04246(11) Uani 1 1 d . . . . .
N1 N 0.4026(6) 0.1306(13) 0.2821(3) 0.0329(8) Uani 1 1 d . . . . .
F1 F 0.6278(9) 0.0054(7) 0.0664(5) 0.0819(13) Uani 1 1 d . . . . .
C1 C 0.5366(17) -0.0382(11) 0.2814(9) 0.0364(19) Uani 1 1 d . . . . .
H1A H 0.4851 -0.1285 0.3338 0.044 Uiso 1 1 calc R U . . .
H1B H 0.7023 -0.0195 0.3197 0.044 Uiso 1 1 calc R U . . .
C2 C 0.4832(13) -0.0903(9) 0.1307(6) 0.0557(15) Uani 1 1 d . . . . .
H2 H 0.4994 -0.2171 0.1200 0.067 Uiso 1 1 calc R U . . .
C3 C 0.2363(13) -0.0317(10) 0.0731(6) 0.0659(19) Uani 1 1 d . . . . .
H3A H 0.2048 -0.0091 -0.0241 0.079 Uiso 1 1 calc R U . . .
H3B H 0.1290 -0.1208 0.0872 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2113(9) 0.132(3) 0.1476(6) 0.0639(19) Uani 1 1 d . . . . .
H4A H 0.0592 0.1359 0.1650 0.077 Uiso 1 1 calc R U . . .
H4B H 0.2275 0.2339 0.0938 0.077 Uiso 1 1 calc R U . . .
C5 C 0.559(2) 0.2856(15) 0.2866(15) 0.065(3) Uani 1 1 d . . . . .
H5A H 0.4696 0.3916 0.2801 0.097 Uiso 1 1 calc R U . . .
H5B H 0.6276 0.2796 0.2114 0.097 Uiso 1 1 calc R U . . .
H5C H 0.6795 0.2850 0.3710 0.097 Uiso 1 1 calc R U . . .
C6 C 0.3049(9) 0.128(2) 0.4029(5) 0.0501(12) Uani 1 1 d . . . . .
H6A H 0.1961 0.0333 0.3939 0.075 Uiso 1 1 calc R U . . .
H6B H 0.2268 0.2374 0.4076 0.075 Uiso 1 1 calc R U . . .
H6C H 0.4290 0.1130 0.4847 0.075 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
N1 C6 1.494(5) . ?
N1 C5 1.498(13) . ?
N1 C1 1.516(12) . ?
N1 C4 1.526(6) . ?
F1 C2 1.416(8) . ?
C1 C2 1.530(10) . ?
C2 C3 1.498(10) . ?
C3 C4 1.487(18) . ?

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
C6 N1 C5 111.1(9) . . ?
C6 N1 C1 108.5(8) . . ?
C5 N1 C1 110.2(4) . . ?
C6 N1 C4 111.9(4) . . ?
C5 N1 C4 109.3(10) . . ?
C1 N1 C4 105.6(9) . . ?
N1 C1 C2 104.9(6) . . ?
F1 C2 C3 108.8(6) . . ?
F1 C2 C1 109.9(6) . . ?
C3 C2 C1 103.4(6) . . ?
C4 C3 C2 105.9(5) . . ?
C3 C4 N1 107.3(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 C2 141.4(7) . . . . ?
C5 N1 C1 C2 -96.7(8) . . . . ?
C4 N1 C1 C2 21.2(8) . . . . ?
N1 C1 C2 F1 81.4(7) . . . . ?
N1 C1 C2 C3 -34.5(8) . . . . ?
F1 C2 C3 C4 -81.9(7) . . . . ?
C1 C2 C3 C4 34.8(9) . . . . ?
C2 C3 C4 N1 -21.9(9) . . . . ?
C6 N1 C4 C3 -117.8(11) . . . . ?
C5 N1 C4 C3 118.6(10) . . . . ?
C1 N1 C4 C3 0.1(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A I1 0.97 3.28 4.075(10) 140.8 2_646
C3 H3A I1 0.97 3.15 4.088(6) 162.2 1_454
C3 H3B I1 0.97 3.27 4.074(8) 141.4 2_646
C5 H5A I1 0.96 3.26 4.139(14) 152.9 2_656
C5 H5B F1 0.96 2.56 3.199(16) 124.3 .
C6 H6A I1 0.96 3.31 4.183(16) 152.6 2_646
C6 H6B I1 0.96 3.18 4.084(15) 158.4 2_656

_refine_diff_density_max         0.258
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.100



####################################################################### 
# 
# 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_P21n
_database_code_depnum_ccdc_archive 'CCDC 1995558'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-18 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 H14 N, I'
_chemical_formula_sum            'C6 H14 I N'
_chemical_formula_weight         227.08

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'
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                   7.2325(2)
_cell_length_b                   11.9157(3)
_cell_length_c                   10.4951(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.932(2)
_cell_angle_gamma                90
_cell_volume                     901.12(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3802
_cell_measurement_theta_min      2.6550
_cell_measurement_theta_max      30.8310

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.474
_shelx_estimated_absorpt_T_min   0.558
_shelx_estimated_absorpt_T_max   0.574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_T_max  0.535
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7171
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.592
_diffrn_reflns_theta_max         26.973
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1969
_reflns_number_gt                1827
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0282P)²+0.5100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1969
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0510
_refine_ls_wR_factor_gt          0.0504
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.18448(2) 0.58806(2) 0.30174(2) 0.04937(7) Uani 1 1 d . . . . .
N1 N 0.1888(3) 0.72375(15) 0.90901(18) 0.0432(4) Uani 1 1 d . . . . .
C1 C 0.1885(4) 0.7464(3) 0.7678(3) 0.0618(7) Uani 1 1 d . . . . .
H1A H 0.2718 0.8076 0.7518 0.074 Uiso 1 1 calc R U . . .
H1B H 0.0647 0.7651 0.7310 0.074 Uiso 1 1 calc R U . . .
C2 C 0.2544(6) 0.6380(3) 0.7130(3) 0.0846(10) Uani 1 1 d . . . . .
H2A H 0.3407 0.6532 0.6493 0.101 Uiso 1 1 calc R U . . .
H2B H 0.1501 0.5962 0.6727 0.101 Uiso 1 1 calc R U . . .
C3 C 0.3490(6) 0.5716(3) 0.8229(4) 0.0917(12) Uani 1 1 d . . . . .
H3A H 0.2786 0.5046 0.8391 0.110 Uiso 1 1 calc R U . . .
H3B H 0.4731 0.5497 0.8045 0.110 Uiso 1 1 calc R U . . .
C4 C 0.3559(4) 0.6501(2) 0.9359(3) 0.0623(7) Uani 1 1 d . . . . .
H4A H 0.3488 0.6088 1.0150 0.075 Uiso 1 1 calc R U . . .
H4B H 0.4691 0.6941 0.9420 0.075 Uiso 1 1 calc R U . . .
C5 C 0.2066(4) 0.8290(2) 0.9851(3) 0.0666(7) Uani 1 1 d . . . . .
H5A H 0.1036 0.8774 0.9605 0.100 Uiso 1 1 calc R U . . .
H5B H 0.3202 0.8662 0.9696 0.100 Uiso 1 1 calc R U . . .
H5C H 0.2074 0.8115 1.0744 0.100 Uiso 1 1 calc R U . . .
C6 C 0.0154(3) 0.6640(2) 0.9373(2) 0.0524(5) Uani 1 1 d . . . . .
H6A H 0.0229 0.6440 1.0262 0.079 Uiso 1 1 calc R U . . .
H6B H 0.0013 0.5973 0.8861 0.079 Uiso 1 1 calc R U . . .
H6C H -0.0894 0.7123 0.9179 0.079 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
N1 C5 1.487(3) . ?
N1 C6 1.494(3) . ?
N1 C4 1.500(3) . ?
N1 C1 1.507(3) . ?
C1 C2 1.508(5) . ?
C2 C3 1.514(6) . ?
C3 C4 1.509(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
C5 N1 C6 109.28(19) . . ?
C5 N1 C4 111.2(2) . . ?
C6 N1 C4 111.11(19) . . ?
C5 N1 C1 111.7(2) . . ?
C6 N1 C1 110.53(19) . . ?
C4 N1 C1 102.9(2) . . ?
N1 C1 C2 104.3(2) . . ?
C1 C2 C3 107.1(3) . . ?
C4 C3 C2 104.9(3) . . ?
N1 C4 C3 104.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 155.7(2) . . . . ?
C6 N1 C1 C2 -82.4(3) . . . . ?
C4 N1 C1 C2 36.3(3) . . . . ?
N1 C1 C2 C3 -18.2(4) . . . . ?
C1 C2 C3 C4 -6.8(4) . . . . ?
C5 N1 C4 C3 -160.7(3) . . . . ?
C6 N1 C4 C3 77.4(3) . . . . ?
C1 N1 C4 C3 -40.9(3) . . . . ?
C2 C3 C4 N1 29.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6C I1 0.96 3.08 3.987(3) 158.5 4_576
C6 H6B I1 0.96 3.18 4.097(3) 160.2 3_566
C6 H6A I1 0.96 3.10 4.017(3) 161.1 1_556
C3 H3B I1 0.97 3.25 4.180(3) 161.9 3_666
C2 H2B I1 0.97 3.30 4.156(4) 148.8 3_566
C1 H1A I1 0.97 3.23 4.083(3) 147.1 4_676

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.106



####################################################################### 
# 
# 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_P21c
_database_code_depnum_ccdc_archive 'CCDC 1995559'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-18 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         ?
_chemical_formula_sum            'C6 H13 F I N'
_chemical_formula_weight         245.07

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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.27230(10)
_cell_length_b                   10.4559(2)
_cell_length_c                   11.9429(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.868(2)
_cell_angle_gamma                90
_cell_volume                     899.57(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8076
_cell_measurement_theta_min      2.6050
_cell_measurement_theta_max      31.0730

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    3.503
_shelx_estimated_absorpt_T_min   0.513
_shelx_estimated_absorpt_T_max   0.527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_T_max  0.479
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8115
_diffrn_reflns_av_unetI/netI     0.0091
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_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         2.600
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1597
_reflns_number_gt                1540
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0261P)²+0.6682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1597
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0170
_refine_ls_wR_factor_ref         0.0458
_refine_ls_wR_factor_gt          0.0453
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.002
_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 0.73575(2) 0.81484(2) 0.09656(2) 0.04548(8) Uani 1 1 d . . . . .
N1 N 0.7213(3) 0.41786(19) 0.22088(15) 0.0365(4) Uani 1 1 d . . . . .
F1 F 0.7972(3) 0.3840(2) -0.03072(13) 0.0755(5) Uani 1 1 d . . . . .
C1 C 0.8831(3) 0.4503(2) 0.15958(19) 0.0410(5) Uani 1 1 d . . . . .
H1A H 0.8642 0.5325 0.1220 0.049 Uiso 1 1 calc R U . . .
H1B H 0.9976 0.4535 0.2118 0.049 Uiso 1 1 calc R U . . .
C2 C 0.8903(4) 0.3451(3) 0.0748(2) 0.0527(6) Uani 1 1 d . . . . .
H2 H 1.0193 0.3225 0.0686 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7894(5) 0.2320(3) 0.1186(3) 0.0677(8) Uani 1 1 d . . . . .
H3A H 0.6806 0.2099 0.0658 0.081 Uiso 1 1 calc R U . . .
H3B H 0.8704 0.1581 0.1291 0.081 Uiso 1 1 calc R U . . .
C4 C 0.7336(4) 0.2749(3) 0.2309(2) 0.0535(7) Uani 1 1 d . . . . .
H4A H 0.6148 0.2386 0.2422 0.064 Uiso 1 1 calc R U . . .
H4B H 0.8262 0.2499 0.2933 0.064 Uiso 1 1 calc R U . . .
C5 C 0.7399(4) 0.4828(3) 0.3337(2) 0.0557(7) Uani 1 1 d . . . . .
H5A H 0.8542 0.4571 0.3780 0.084 Uiso 1 1 calc R U . . .
H5B H 0.6376 0.4589 0.3723 0.084 Uiso 1 1 calc R U . . .
H5C H 0.7399 0.5738 0.3232 0.084 Uiso 1 1 calc R U . . .
C6 C 0.5406(3) 0.4570(3) 0.1538(2) 0.0462(6) Uani 1 1 d . . . . .
H6A H 0.5438 0.5468 0.1372 0.069 Uiso 1 1 calc R U . . .
H6B H 0.4411 0.4399 0.1968 0.069 Uiso 1 1 calc R U . . .
H6C H 0.5214 0.4095 0.0844 0.069 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
N1 C5 1.498(3) . ?
N1 C6 1.500(3) . ?
N1 C4 1.501(3) . ?
N1 C1 1.507(3) . ?
F1 C2 1.407(3) . ?
C1 C2 1.500(4) . ?
C2 C3 1.522(5) . ?
C3 C4 1.521(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
C5 N1 C6 108.76(19) . . ?
C5 N1 C4 112.5(2) . . ?
C6 N1 C4 110.65(19) . . ?
C5 N1 C1 110.76(18) . . ?
C6 N1 C1 111.36(17) . . ?
C4 N1 C1 102.78(18) . . ?
C2 C1 N1 105.3(2) . . ?
F1 C2 C1 109.6(2) . . ?
F1 C2 C3 109.7(2) . . ?
C1 C2 C3 106.0(2) . . ?
C4 C3 C2 105.8(2) . . ?
N1 C4 C3 104.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 158.3(2) . . . . ?
C6 N1 C1 C2 -80.5(2) . . . . ?
C4 N1 C1 C2 37.9(2) . . . . ?
N1 C1 C2 F1 96.3(2) . . . . ?
N1 C1 C2 C3 -22.0(3) . . . . ?
F1 C2 C3 C4 -120.5(3) . . . . ?
C1 C2 C3 C4 -2.2(3) . . . . ?
C5 N1 C4 C3 -158.1(2) . . . . ?
C6 N1 C4 C3 80.1(3) . . . . ?
C1 N1 C4 C3 -38.9(3) . . . . ?
C2 C3 C4 N1 25.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6C F1 0.96 2.60 3.169(3) 118.6 .
C6 H6B I1 0.96 3.21 4.097(2) 153.8 2_645
C6 H6A I1 0.96 3.20 4.092(3) 155.7 .
C5 H5B I1 0.96 3.17 4.066(3) 155.8 2_645
C5 H5A I1 0.96 3.31 4.177(3) 151.4 2_745
C4 H4B F1 0.97 2.56 3.275(3) 130.8 4_566
C2 H2 I1 0.98 3.18 3.988(3) 141.3 3_765
C1 H1B I1 0.97 3.14 3.995(2) 147.3 2_745
C1 H1A I1 0.97 3.10 4.003(2) 155.6 .

_refine_diff_density_max         0.503
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_S_P21
_database_code_depnum_ccdc_archive 'CCDC 1995557'
loop_
_audit_author_name
_audit_author_address
'Yong Ai'
;Nanchang University
China
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-18 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 H13 F N, I'
_chemical_formula_sum            'C6 H13 F I N'
_chemical_formula_weight         245.07

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.9585(2)
_cell_length_b                   7.6205(3)
_cell_length_c                   10.1558(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.571(4)
_cell_angle_gamma                90
_cell_volume                     444.22(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3240
_cell_measurement_theta_min      2.6610
_cell_measurement_theta_max      30.5840

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    3.547
_shelx_estimated_absorpt_T_min   0.509
_shelx_estimated_absorpt_T_max   0.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.463
_exptl_absorpt_correction_T_max  0.475
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3005
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_av_R_equivalents  0.0082
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.389
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1746
_reflns_number_gt                1556
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0283P)²+0.3793P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1746
_refine_ls_number_parameters     85
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0474
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_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 0.03369(4) 0.7179(2) 0.32365(3) 0.04220(11) Uani 1 1 d . . . . .
N1 N 0.5979(6) 0.7080(12) 0.7187(3) 0.0324(8) Uani 1 1 d . . . . .
F1 F 0.3721(9) 0.8351(7) 0.9337(5) 0.0816(13) Uani 1 1 d . . . . .
C1 C 0.4644(17) 0.8781(10) 0.7195(9) 0.0359(19) Uani 1 1 d . . . . .
H1A H 0.2986 0.8602 0.6809 0.043 Uiso 1 1 calc R U . . .
H1B H 0.5171 0.9683 0.6674 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5170(12) 0.9295(9) 0.8697(6) 0.0545(14) Uani 1 1 d . . . . .
H2 H 0.5004 1.0563 0.8801 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7637(13) 0.8725(10) 0.9271(6) 0.0647(18) Uani 1 1 d . . . . .
H3A H 0.7960 0.8513 1.0246 0.078 Uiso 1 1 calc R U . . .
H3B H 0.8702 0.9615 0.9117 0.078 Uiso 1 1 calc R U . . .
C4 C 0.7885(9) 0.705(3) 0.8523(6) 0.062(2) Uani 1 1 d . . . . .
H4A H 0.7708 0.6034 0.9063 0.074 Uiso 1 1 calc R U . . .
H4B H 0.9406 0.6997 0.8348 0.074 Uiso 1 1 calc R U . . .
C5 C 0.440(2) 0.5532(15) 0.7121(15) 0.062(3) Uani 1 1 d . . . . .
H5A H 0.3171 0.5577 0.6288 0.093 Uiso 1 1 calc R U . . .
H5B H 0.3748 0.5558 0.7887 0.093 Uiso 1 1 calc R U . . .
H5C H 0.5276 0.4469 0.7144 0.093 Uiso 1 1 calc R U . . .
C6 C 0.6956(9) 0.714(2) 0.5974(5) 0.0498(11) Uani 1 1 d . . . . .
H6A H 0.5709 0.7281 0.5157 0.075 Uiso 1 1 calc R U . . .
H6B H 0.7770 0.6065 0.5922 0.075 Uiso 1 1 calc R U . . .
H6C H 0.8015 0.8109 0.6067 0.075 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
N1 C6 1.497(5) . ?
N1 C5 1.498(13) . ?
N1 C4 1.518(6) . ?
N1 C1 1.522(11) . ?
F1 C2 1.409(8) . ?
C1 C2 1.523(10) . ?
C2 C3 1.493(10) . ?
C3 C4 1.514(18) . ?

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
C6 N1 C5 111.4(9) . . ?
C6 N1 C4 111.9(4) . . ?
C5 N1 C4 109.8(10) . . ?
C6 N1 C1 107.3(8) . . ?
C5 N1 C1 110.4(4) . . ?
C4 N1 C1 106.0(9) . . ?
N1 C1 C2 104.9(6) . . ?
F1 C2 C3 109.4(5) . . ?
F1 C2 C1 110.1(6) . . ?
C3 C2 C1 103.5(6) . . ?
C2 C3 C4 105.5(5) . . ?
C3 C4 N1 106.6(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 C2 -141.1(7) . . . . ?
C5 N1 C1 C2 97.4(8) . . . . ?
C4 N1 C1 C2 -21.4(8) . . . . ?
N1 C1 C2 F1 -81.5(7) . . . . ?
N1 C1 C2 C3 35.4(8) . . . . ?
F1 C2 C3 C4 81.6(7) . . . . ?
C1 C2 C3 C4 -35.8(8) . . . . ?
C2 C3 C4 N1 22.7(9) . . . . ?
C6 N1 C4 C3 116.2(11) . . . . ?
C5 N1 C4 C3 -119.6(10) . . . . ?
C1 N1 C4 C3 -0.4(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6C I1 0.96 3.27 4.159(16) 154.4 2_656
C6 H6B I1 0.96 3.20 4.103(15) 157.0 2_646
C5 H5C I1 0.96 3.25 4.135(14) 153.9 2_646
C5 H5B F1 0.96 2.59 3.215(15) 122.9 .
C3 H3B I1 0.97 3.25 4.064(7) 142.2 2_656
C3 H3A I1 0.97 3.16 4.089(6) 162.0 1_656
C1 H1B I1 0.97 3.26 4.067(10) 141.3 2_656

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.102



