# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_p21m
_database_code_depnum_ccdc_archive 'CCDC 1521065'
_audit_update_record             
;
2016-12-06 deposited with the CCDC.
2017-01-09 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 H16 I N'
_chemical_formula_weight         229.10

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           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.2911(14)
_cell_length_b                   8.3667(14)
_cell_length_c                   8.3092(14)
_cell_angle_alpha                90
_cell_angle_beta                 118.950(11)
_cell_angle_gamma                90
_cell_volume                     504.38(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    405(2)
_cell_measurement_reflns_used    1308
_cell_measurement_theta_min      2.7983
_cell_measurement_theta_max      29.6948

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    3.104

_exptl_absorpt_correction_T_min  0.68933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      405(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_detector_area_resol_mean 8.4350
_diffrn_reflns_number            5046
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.801
_diffrn_reflns_theta_max         25.677
_diffrn_reflns_theta_full        25.677
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1018
_reflns_number_gt                422
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_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)+(0.0970P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
#_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1018
_refine_ls_number_parameters     37
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   0.808
_refine_ls_restrained_S_all      0.904
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.010

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 0.34981(6) 0.2500 0.64795(6) 0.12478(19) Uani 1 2 d S T P . .
C4 C 0.6222(6) 0.2500 0.2974(5) 0.229(6) Uiso 1 2 d DS . P . .
C3 C 0.9152(14) 0.1234(5) 0.7106(12) 0.244(9) Uiso 0.5 1 d D . P . .
H3A H 0.8110 0.0753 0.7123 0.367 Uiso 0.5 1 calc R U P . .
H3B H 1.0182 0.1243 0.8329 0.367 Uiso 0.5 1 calc R U P . .
H3C H 0.9465 0.0630 0.6313 0.367 Uiso 0.5 1 calc R U P . .
C1 C 0.8676(8) 0.2948(6) 0.6394(6) 0.162(5) Uiso 0.5 1 d D . P . .
N1 N 0.6778(6) 0.3051(5) 0.4812(4) 0.217(6) Uiso 0.5 1 d D . P . .
H1A H 0.6054 0.2547 0.5164 0.260 Uiso 0.5 2 calc R U P . .
H1B H 0.6466 0.4079 0.4707 0.260 Uiso 0.5 1 calc R U P . .
C6 C 0.7554(5) 0.2152(9) 0.2360(5) 0.110(3) Uiso 0.5 1 d D . P . .
H6A H 0.8427 0.3011 0.2709 0.165 Uiso 0.5 1 calc R U P . .
H6B H 0.6926 0.2038 0.1046 0.165 Uiso 0.5 1 calc R U P . .
H6C H 0.8189 0.1177 0.2917 0.165 Uiso 0.5 1 calc R U P . .
C5 C 0.4236(6) 0.2500 0.1632(9) 0.231(6) Uiso 1 2 d DS . P . .
H5A H 0.3545 0.2767 0.2245 0.347 Uiso 0.5 1 calc R U P . .
H5B H 0.3878 0.1459 0.1088 0.347 Uiso 0.5 1 calc R U P . .
H5C H 0.3994 0.3274 0.0689 0.347 Uiso 0.5 1 calc R U P . .
C2 C 0.8983(13) 0.4061(6) 0.7934(6) 0.163(5) Uiso 0.5 1 d D . P . .
H2A H 0.8763 0.5141 0.7488 0.245 Uiso 0.5 1 calc R U P . .
H2B H 1.0231 0.3961 0.8908 0.245 Uiso 0.5 1 calc R U P . .
H2C H 0.8152 0.3793 0.8390 0.245 Uiso 0.5 1 calc R U P . .
H1 H 0.9473 0.2878 0.5973 0.245 Uiso 0.5 1 d . U P . .
H4 H 0.6039 0.1572 0.3406 0.245 Uiso 0.5 1 d . U P . .


_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




C4 N1 1.441(5) . ?
C4 C6 1.453(6) . ?
C4 C5 1.475(5) . ?
C4 H4 0.8991 . ?
C3 C1 1.528(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C1 N1 1.487(5) . ?
C1 C2 1.501(6) . ?
C1 H1 0.8867 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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

N1 C4 C6 121.9(3) . . ?
N1 C4 C6 121.9(3) 4_565 4_565 ?
N1 C4 C5 117.9(5) . . ?
C6 C4 C5 119.6(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
N1 H1A I1 0.89 2.82 3.629(6) 152.5 4_565
N1 H1A I1 0.89 2.82 3.629(6) 152.5 .
N1 H1B I1 0.89 3.03 3.850(4) 153.7 3_666

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.619
_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_115
_database_code_depnum_ccdc_archive 'CCDC 1521066'
_audit_update_record             
;
2016-12-06 deposited with the CCDC.
2017-01-09 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 H16 I N'
_chemical_formula_weight         229.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.35190(10)
_cell_length_b                   8.3673(2)
_cell_length_c                   14.2217(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     993.85(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3842
_cell_measurement_theta_min      2.8210
_cell_measurement_theta_max      29.3591

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    3.151
_exptl_absorpt_correction_T_min  0.88178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire1, long nozzle'
_diffrn_detector_area_resol_mean 8.4350
_diffrn_reflns_number            11297
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0381
_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       17
_diffrn_reflns_theta_min         2.824
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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             1891
_reflns_number_gt                1348
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.996
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_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)+(0.0122P)²+1.5200P] 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       0.0184(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1891
_refine_ls_number_parameters     90
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0534
_refine_ls_wR_factor_gt          0.0490
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.010
_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
I1 I 0.73933(4) 0.75168(8) 0.86033(3) 0.0609(2) Uani 1 1 d . . . . .
N1 N 1.3257(8) 0.8448(8) 0.8999(5) 0.0520(16) Uani 1 1 d . . . . .
H1A H 1.431(8) 0.819(8) 0.890(5) 0.062 Uiso 1 1 d . U . . .
H1B H 1.306(9) 0.828(8) 0.952(5) 0.062 Uiso 1 1 d . U . . .
C1 C 1.3005(11) 1.0219(9) 0.8882(6) 0.059(2) Uani 1 1 d D . . . .
C2 C 1.4162(10) 1.1073(10) 0.9519(6) 0.077(3) Uani 1 1 d . . . . .
H2A H 1.5234 1.0733 0.9379 0.116 Uiso 1 1 calc R U . . .
H2B H 1.3916 1.0825 1.0162 0.116 Uiso 1 1 calc R U . . .
H2C H 1.4074 1.2205 0.9422 0.116 Uiso 1 1 calc R U . . .
C3 C 1.1298(10) 1.0668(11) 0.9059(8) 0.088(3) Uani 1 1 d . . . . .
H3A H 1.1166 1.1796 0.8965 0.131 Uiso 1 1 calc R U . . .
H3B H 1.1016 1.0398 0.9694 0.131 Uiso 1 1 calc R U . . .
H3C H 1.0617 1.0097 0.8631 0.131 Uiso 1 1 calc R U . . .
C4 C 1.2313(8) 0.7299(12) 0.8397(5) 0.064(2) Uani 1 1 d D . . . .
C5 C 1.2659(11) 0.7616(12) 0.7370(5) 0.094(2) Uani 1 1 d . . . . .
H5A H 1.2121 0.6833 0.6991 0.141 Uiso 1 1 calc R U . . .
H5B H 1.3792 0.7552 0.7261 0.141 Uiso 1 1 calc R U . . .
H5C H 1.2283 0.8664 0.7205 0.141 Uiso 1 1 calc R U . . .
C6 C 1.2730(13) 0.5599(9) 0.8683(6) 0.082(3) Uani 1 1 d . . . . .
H6A H 1.2522 0.5459 0.9342 0.122 Uiso 1 1 calc R U . . .
H6B H 1.3843 0.5402 0.8559 0.122 Uiso 1 1 calc R U . . .
H6C H 1.2089 0.4861 0.8329 0.122 Uiso 1 1 calc R U . . .
H4 H 1.128(4) 0.753(13) 0.853(5) 0.098 Uiso 1 1 d D U . . .
H1 H 1.322(11) 1.049(10) 0.828(2) 0.098 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
N1 C4 1.509(10) . ?
N1 C1 1.506(9) . ?
N1 H1A 0.92(7) . ?
N1 H1B 0.77(7) . ?
C1 C3 1.496(12) . ?
C1 C2 1.505(11) . ?
C1 H1 0.905(13) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.513(10) . ?
C4 C6 1.520(12) . ?
C4 H4 0.901(13) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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 C1 119.4(7) . . ?
C4 N1 H1A 105(4) . . ?
C1 N1 H1A 110(4) . . ?
C4 N1 H1B 109(6) . . ?
C1 N1 H1B 105(6) . . ?
H1A N1 H1B 108(7) . . ?
C3 C1 C2 113.0(8) . . ?
C3 C1 N1 111.2(7) . . ?
C2 C1 N1 108.1(7) . . ?
C3 C1 H1 107(6) . . ?
C2 C1 H1 109(6) . . ?
N1 C1 H1 109(6) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 109.6(7) . . ?
N1 C4 C6 109.0(7) . . ?
C5 C4 C6 112.2(7) . . ?
N1 C4 H4 104(6) . . ?
C5 C4 H4 110(5) . . ?
C6 C4 H4 112(7) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
N1 H1B I1 0.77(7) 2.81(7) 3.577(6) 176(7) 4_567
N1 H1A I1 0.92(7) 2.67(7) 3.586(7) 179(6) 1_655

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.078



