# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_5
_database_code_depnum_ccdc_archive 'CCDC 1025434'
_audit_update_record             
;
2014-11-06 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Cl6 I2 N2'
_chemical_formula_weight         622.68

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   8.0564(16)
_cell_length_b                   13.093(3)
_cell_length_c                   16.894(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.39(3)
_cell_angle_gamma                90.00
_cell_volume                     1767.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    4.456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4021
_exptl_absorpt_correction_T_max  0.5180
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8218
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3084
_reflns_number_gt                2780
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXP
_computing_publication_material  SHELXP

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0309P)²+0.0123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3084
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0557
_refine_ls_wR_factor_gt          0.0536
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.21942(3) 0.302055(16) 0.163022(12) 0.02118(8) Uani 1 1 d . . .
I1 I 0.14201(3) 0.366299(16) 0.430749(12) 0.02158(8) Uani 1 1 d . . .
Cl3 Cl -0.06164(11) 0.32542(7) 0.20529(5) 0.0307(2) Uani 1 1 d . . .
Cl4 Cl 0.27598(12) 0.15995(8) 0.26457(6) 0.0363(2) Uani 1 1 d . . .
Cl5 Cl 0.50507(12) 0.28002(7) 0.12072(6) 0.0371(2) Uani 1 1 d . . .
Cl1 Cl 0.26583(13) 0.53899(7) 0.44702(6) 0.0363(2) Uani 1 1 d . . .
Cl6 Cl 0.15530(12) 0.44426(7) 0.06874(6) 0.0347(2) Uani 1 1 d . . .
Cl2 Cl 0.38313(12) 0.26482(8) 0.48746(6) 0.0395(2) Uani 1 1 d . . .
N1 N -0.1148(4) 0.4246(2) 0.37698(16) 0.0219(6) Uani 1 1 d . . .
N2 N -0.0287(3) 0.2293(2) 0.40577(16) 0.0218(6) Uani 1 1 d . . .
C6 C -0.2390(4) 0.3556(3) 0.3636(2) 0.0232(8) Uani 1 1 d . . .
C5 C -0.1928(4) 0.2481(3) 0.37935(19) 0.0220(7) Uani 1 1 d . . .
C2 C -0.1428(5) 0.5239(3) 0.3609(2) 0.0298(8) Uani 1 1 d . . .
H2A H -0.0533 0.5713 0.3703 0.036 Uiso 1 1 calc R . .
C1 C 0.0274(5) 0.1338(3) 0.4174(2) 0.0284(8) Uani 1 1 d . . .
H1A H 0.1424 0.1225 0.4358 0.034 Uiso 1 1 calc R . .
C11 C -0.3988(5) 0.3862(3) 0.3333(2) 0.0290(8) Uani 1 1 d . . .
H11A H -0.4866 0.3376 0.3234 0.035 Uiso 1 1 calc R . .
C10 C -0.3024(5) 0.1678(3) 0.3667(2) 0.0314(9) Uani 1 1 d . . .
H10A H -0.4176 0.1802 0.3496 0.038 Uiso 1 1 calc R . .
C9 C -0.3004(5) 0.5575(3) 0.3310(2) 0.0372(10) Uani 1 1 d . . .
H9A H -0.3199 0.6279 0.3196 0.045 Uiso 1 1 calc R . .
C8 C -0.0771(5) 0.0526(3) 0.4033(2) 0.0330(9) Uani 1 1 d . . .
H8A H -0.0349 -0.0150 0.4103 0.040 Uiso 1 1 calc R . .
C4 C -0.4290(5) 0.4883(3) 0.3176(2) 0.0366(10) Uani 1 1 d . . .
H4A H -0.5385 0.5108 0.2977 0.044 Uiso 1 1 calc R . .
C3 C -0.2448(5) 0.0689(3) 0.3788(2) 0.0345(9) Uani 1 1 d . . .
H3A H -0.3199 0.0129 0.3704 0.041 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 Cl6 2.4615(10) . ?
I2 Cl3 2.4792(10) . ?
I2 Cl5 2.5125(11) . ?
I2 Cl4 2.5320(10) . ?
I1 N2 2.267(3) . ?
I1 N1 2.282(3) . ?
I1 Cl2 2.4450(11) . ?
I1 Cl1 2.4724(10) . ?
N1 C2 1.341(4) . ?
N1 C6 1.345(4) . ?
N2 C1 1.335(4) . ?
N2 C5 1.363(4) . ?
C6 C11 1.382(5) . ?
C6 C5 1.472(5) . ?
C5 C10 1.372(5) . ?
C2 C9 1.377(6) . ?
C2 H2A 0.9500 . ?
C1 C8 1.358(5) . ?
C1 H1A 0.9500 . ?
C11 C4 1.378(6) . ?
C11 H11A 0.9500 . ?
C10 C3 1.382(5) . ?
C10 H10A 0.9500 . ?
C9 C4 1.373(6) . ?
C9 H9A 0.9500 . ?
C8 C3 1.378(6) . ?
C8 H8A 0.9500 . ?
C4 H4A 0.9500 . ?
C3 H3A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl6 I2 Cl3 88.26(4) . . ?
Cl6 I2 Cl5 91.52(4) . . ?
Cl3 I2 Cl5 179.46(3) . . ?
Cl6 I2 Cl4 177.12(3) . . ?
Cl3 I2 Cl4 89.26(4) . . ?
Cl5 I2 Cl4 90.96(4) . . ?
N2 I1 N1 72.14(10) . . ?
N2 I1 Cl2 94.31(8) . . ?
N1 I1 Cl2 166.39(8) . . ?
N2 I1 Cl1 166.16(8) . . ?
N1 I1 Cl1 94.06(7) . . ?
Cl2 I1 Cl1 99.47(4) . . ?
C2 N1 C6 121.0(3) . . ?
C2 N1 I1 121.7(2) . . ?
C6 N1 I1 117.4(2) . . ?
C1 N2 C5 120.9(3) . . ?
C1 N2 I1 121.9(2) . . ?
C5 N2 I1 117.2(2) . . ?
N1 C6 C11 120.3(3) . . ?
N1 C6 C5 116.5(3) . . ?
C11 C6 C5 123.1(3) . . ?
N2 C5 C10 119.4(3) . . ?
N2 C5 C6 116.4(3) . . ?
C10 C5 C6 124.2(3) . . ?
N1 C2 C9 120.5(4) . . ?
N1 C2 H2A 119.7 . . ?
C9 C2 H2A 119.7 . . ?
N2 C1 C8 121.1(4) . . ?
N2 C1 H1A 119.5 . . ?
C8 C1 H1A 119.5 . . ?
C4 C11 C6 119.0(4) . . ?
C4 C11 H11A 120.5 . . ?
C6 C11 H11A 120.5 . . ?
C5 C10 C3 119.9(4) . . ?
C5 C10 H10A 120.1 . . ?
C3 C10 H10A 120.1 . . ?
C4 C9 C2 119.3(4) . . ?
C4 C9 H9A 120.3 . . ?
C2 C9 H9A 120.3 . . ?
C1 C8 C3 119.5(4) . . ?
C1 C8 H8A 120.2 . . ?
C3 C8 H8A 120.2 . . ?
C9 C4 C11 119.9(4) . . ?
C9 C4 H4A 120.1 . . ?
C11 C4 H4A 120.1 . . ?
C8 C3 C10 119.2(4) . . ?
C8 C3 H3A 120.4 . . ?
C10 C3 H3A 120.4 . . ?

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
N2 I1 N1 C2 -176.3(3) . . . . ?
Cl2 I1 N1 C2 178.2(2) . . . . ?
Cl1 I1 N1 C2 4.7(3) . . . . ?
N2 I1 N1 C6 5.2(2) . . . . ?
Cl2 I1 N1 C6 -0.3(5) . . . . ?
Cl1 I1 N1 C6 -173.8(2) . . . . ?
N1 I1 N2 C1 175.8(3) . . . . ?
Cl2 I1 N2 C1 -5.5(3) . . . . ?
Cl1 I1 N2 C1 179.9(2) . . . . ?
N1 I1 N2 C5 -5.2(2) . . . . ?
Cl2 I1 N2 C5 173.5(2) . . . . ?
Cl1 I1 N2 C5 -1.1(5) . . . . ?
C2 N1 C6 C11 -0.4(5) . . . . ?
I1 N1 C6 C11 178.1(2) . . . . ?
C2 N1 C6 C5 176.9(3) . . . . ?
I1 N1 C6 C5 -4.6(4) . . . . ?
C1 N2 C5 C10 1.8(5) . . . . ?
I1 N2 C5 C10 -177.2(2) . . . . ?
C1 N2 C5 C6 -176.2(3) . . . . ?
I1 N2 C5 C6 4.8(4) . . . . ?
N1 C6 C5 N2 -0.1(4) . . . . ?
C11 C6 C5 N2 177.1(3) . . . . ?
N1 C6 C5 C10 -178.0(3) . . . . ?
C11 C6 C5 C10 -0.8(5) . . . . ?
C6 N1 C2 C9 0.6(5) . . . . ?
I1 N1 C2 C9 -177.8(3) . . . . ?
C5 N2 C1 C8 0.0(5) . . . . ?
I1 N2 C1 C8 178.9(3) . . . . ?
N1 C6 C11 C4 -0.4(5) . . . . ?
C5 C6 C11 C4 -177.6(3) . . . . ?
N2 C5 C10 C3 -1.6(5) . . . . ?
C6 C5 C10 C3 176.2(3) . . . . ?
N1 C2 C9 C4 0.0(5) . . . . ?
N2 C1 C8 C3 -1.9(6) . . . . ?
C2 C9 C4 C11 -0.9(6) . . . . ?
C6 C11 C4 C9 1.1(5) . . . . ?
C1 C8 C3 C10 2.0(6) . . . . ?
C5 C10 C3 C8 -0.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.542
_refine_diff_density_min         -1.190
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_HBipyICl2
_database_code_depnum_ccdc_archive 'CCDC 1025435'
_audit_update_record             
;
2014-11-06 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 Cl2 I N2'
_chemical_formula_weight         354.99

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.666(2)
_cell_length_b                   7.9147(16)
_cell_length_c                   13.981(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.62(3)
_cell_angle_gamma                90.00
_cell_volume                     1279.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    2.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4776
_exptl_absorpt_correction_T_max  0.6710
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11753
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.10
_reflns_number_total             2784
_reflns_number_gt                2546
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXP
_computing_publication_material  SHELXP

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0219P)²+0.5459P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0495
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.747772(13) 0.018555(18) 0.235341(11) 0.02901(7) Uani 1 1 d . . .
Cl2 Cl 0.91788(6) 0.17112(9) 0.33627(5) 0.04124(16) Uani 1 1 d . . .
Cl1 Cl 0.58123(6) -0.12242(9) 0.13451(5) 0.04669(18) Uani 1 1 d . . .
N2 N 0.7952(2) 0.4740(3) 0.12571(16) 0.0365(5) Uani 1 1 d . . .
C5 C 0.7707(2) 0.5513(3) 0.28535(18) 0.0291(5) Uani 1 1 d . . .
N1 N 0.88042(19) 0.6040(2) 0.29111(15) 0.0309(4) Uani 1 1 d . . .
C6 C 0.7212(2) 0.4804(3) 0.19089(19) 0.0300(5) Uani 1 1 d . . .
C7 C 0.6079(2) 0.4254(3) 0.1724(2) 0.0367(6) Uani 1 1 d . . .
H7A H 0.5572 0.4328 0.2201 0.044 Uiso 1 1 calc R . .
C8 C 0.5705(3) 0.3587(3) 0.0814(2) 0.0441(7) Uani 1 1 d . . .
H8A H 0.4934 0.3191 0.0661 0.053 Uiso 1 1 calc R . .
C4 C 0.7151(2) 0.5667(3) 0.36590(19) 0.0377(6) Uani 1 1 d . . .
H4A H 0.6374 0.5297 0.3644 0.045 Uiso 1 1 calc R . .
C10 C 0.7563(3) 0.4101(4) 0.03892(19) 0.0448(7) Uani 1 1 d . . .
H10A H 0.8078 0.4055 -0.0083 0.054 Uiso 1 1 calc R . .
C9 C 0.6451(3) 0.3506(3) 0.0146(2) 0.0462(7) Uani 1 1 d . . .
H9A H 0.6211 0.3048 -0.0477 0.055 Uiso 1 1 calc R . .
C1 C 0.9394(3) 0.6734(3) 0.36979(19) 0.0416(6) Uani 1 1 d . . .
H1A H 1.0168 0.7106 0.3693 0.050 Uiso 1 1 calc R . .
C2 C 0.8867(3) 0.6900(4) 0.4511(2) 0.0484(7) Uani 1 1 d . . .
H2A H 0.9272 0.7377 0.5082 0.058 Uiso 1 1 calc R . .
C3 C 0.7737(3) 0.6363(4) 0.4489(2) 0.0487(7) Uani 1 1 d . . .
H3A H 0.7361 0.6475 0.5048 0.058 Uiso 1 1 calc R . .
H1 H 0.917(3) 0.590(4) 0.238(2) 0.046(8) Uiso 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
I1 Cl1 2.5060(9) . ?
I1 Cl2 2.5776(9) . ?
N2 C6 1.337(4) . ?
N2 C10 1.337(3) . ?
C5 N1 1.338(3) . ?
C5 C4 1.377(4) . ?
C5 C6 1.480(4) . ?
N1 C1 1.336(3) . ?
N1 H1 0.91(3) . ?
C6 C7 1.383(4) . ?
C7 C8 1.393(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.360(4) . ?
C8 H8A 0.9500 . ?
C4 C3 1.381(4) . ?
C4 H4A 0.9500 . ?
C10 C9 1.380(4) . ?
C10 H10A 0.9500 . ?
C9 H9A 0.9500 . ?
C1 C2 1.369(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.381(4) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 I1 Cl2 178.41(2) . . ?
C6 N2 C10 117.4(3) . . ?
N1 C5 C4 118.3(2) . . ?
N1 C5 C6 115.4(2) . . ?
C4 C5 C6 126.3(3) . . ?
C1 N1 C5 124.2(2) . . ?
C1 N1 H1 118.2(19) . . ?
C5 N1 H1 117.6(19) . . ?
N2 C6 C7 123.2(3) . . ?
N2 C6 C5 114.3(2) . . ?
C7 C6 C5 122.5(3) . . ?
C6 C7 C8 117.8(3) . . ?
C6 C7 H7A 121.1 . . ?
C8 C7 H7A 121.1 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
N2 C10 C9 123.2(3) . . ?
N2 C10 H10A 118.4 . . ?
C9 C10 H10A 118.4 . . ?
C8 C9 C10 118.7(3) . . ?
C8 C9 H9A 120.6 . . ?
C10 C9 H9A 120.6 . . ?
N1 C1 C2 119.0(3) . . ?
N1 C1 H1A 120.5 . . ?
C2 C1 H1A 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C5 N1 C1 -1.1(4) . . . . ?
C6 C5 N1 C1 179.2(2) . . . . ?
C10 N2 C6 C7 -0.3(4) . . . . ?
C10 N2 C6 C5 179.5(2) . . . . ?
N1 C5 C6 N2 2.2(3) . . . . ?
C4 C5 C6 N2 -177.5(2) . . . . ?
N1 C5 C6 C7 -177.9(2) . . . . ?
C4 C5 C6 C7 2.3(4) . . . . ?
N2 C6 C7 C8 0.7(4) . . . . ?
C5 C6 C7 C8 -179.2(2) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
N1 C5 C4 C3 0.4(4) . . . . ?
C6 C5 C4 C3 -179.9(2) . . . . ?
C6 N2 C10 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
N2 C10 C9 C8 0.8(4) . . . . ?
C5 N1 C1 C2 1.2(4) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C5 C4 C3 C2 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_nBuNICl4
_database_code_depnum_ccdc_archive 'CCDC 1032987'
_audit_update_record             
;
2014-11-06 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H35 Cl4 I N'
_chemical_formula_weight         510.15

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   14.863(3)
_cell_length_b                   8.7539(18)
_cell_length_c                   18.783(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.06(3)
_cell_angle_gamma                90.00
_cell_volume                     2323.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5910
_exptl_absorpt_correction_T_max  0.7702
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20507
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4077
_reflns_number_gt                3209
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXP
_computing_publication_material  SHELXP

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0502P)²+5.0768P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4077
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.01002(2) 0.37068(3) 0.230032(17) 0.03184(13) Uani 1 1 d . . .
Cl2 Cl -0.15129(10) 0.39632(15) 0.13532(8) 0.0474(3) Uani 1 1 d . . .
Cl3 Cl 0.17159(12) 0.3484(2) 0.31906(9) 0.0655(5) Uani 1 1 d . . .
Cl1 Cl 0.05797(10) 0.19555(16) 0.14349(8) 0.0461(3) Uani 1 1 d . . .
Cl6 Cl -0.03955(13) 0.5390(2) 0.31883(10) 0.0668(5) Uani 1 1 d . . .
N1 N 0.2977(2) 0.6219(4) 0.5515(2) 0.0217(8) Uani 1 1 d . . .
C2 C 0.3990(3) 0.6226(5) 0.5479(3) 0.0251(10) Uani 1 1 d . . .
H2A H 0.4239 0.5390 0.5278 0.030 Uiso 1 1 calc R . .
C3 C 0.2960(3) 0.6491(5) 0.6311(2) 0.0254(10) Uani 1 1 d . . .
H3A H 0.3224 0.7519 0.6469 0.030 Uiso 1 1 calc R . .
H3B H 0.2291 0.6501 0.6304 0.030 Uiso 1 1 calc R . .
C4 C 0.2582(3) 0.4647(5) 0.5238(3) 0.0255(10) Uani 1 1 d . . .
H4A H 0.2643 0.4489 0.4733 0.031 Uiso 1 1 calc R . .
H4B H 0.2981 0.3868 0.5573 0.031 Uiso 1 1 calc R . .
C5 C 0.2383(3) 0.7480(5) 0.5040(3) 0.0254(10) Uani 1 1 d . . .
H5A H 0.1747 0.7450 0.5105 0.030 Uiso 1 1 calc R . .
H5B H 0.2673 0.8473 0.5238 0.030 Uiso 1 1 calc R . .
C6 C 0.1581(4) 0.8670(6) 0.3802(3) 0.0422(13) Uani 1 1 d . . .
H6A H 0.0961 0.8516 0.3885 0.051 Uiso 1 1 calc R . .
H6B H 0.1827 0.9678 0.4013 0.051 Uiso 1 1 calc R . .
C7 C 0.4577(3) 0.7634(5) 0.5780(3) 0.0302(11) Uani 1 1 d . . .
H7A H 0.4638 0.7773 0.6316 0.036 Uiso 1 1 calc R . .
H7B H 0.4264 0.8550 0.5503 0.036 Uiso 1 1 calc R . .
C8 C 0.5557(3) 0.7440(6) 0.5687(3) 0.0349(11) Uani 1 1 d . . .
H8A H 0.5874 0.6550 0.5985 0.042 Uiso 1 1 calc R . .
H8B H 0.5483 0.7222 0.5154 0.042 Uiso 1 1 calc R . .
C9 C 0.3493(4) 0.5349(5) 0.6896(3) 0.0321(11) Uani 1 1 d . . .
H9A H 0.3280 0.4301 0.6728 0.038 Uiso 1 1 calc R . .
H9B H 0.4179 0.5420 0.6962 0.038 Uiso 1 1 calc R . .
C10 C 0.6176(4) 0.8828(6) 0.5928(4) 0.0521(15) Uani 1 1 d . . .
H10A H 0.6793 0.8639 0.5857 0.078 Uiso 1 1 calc R . .
H10B H 0.6265 0.9037 0.6458 0.078 Uiso 1 1 calc R . .
H10C H 0.5874 0.9709 0.5626 0.078 Uiso 1 1 calc R . .
C11 C 0.1563(3) 0.4364(5) 0.5196(3) 0.0321(11) Uani 1 1 d . . .
H11A H 0.1143 0.5021 0.4802 0.038 Uiso 1 1 calc R . .
H11B H 0.1470 0.4637 0.5680 0.038 Uiso 1 1 calc R . .
C12 C 0.3815(4) 0.4540(7) 0.8243(3) 0.0467(14) Uani 1 1 d . . .
H12A H 0.3678 0.4794 0.8707 0.070 Uiso 1 1 calc R . .
H12B H 0.4500 0.4591 0.8331 0.070 Uiso 1 1 calc R . .
H12C H 0.3590 0.3505 0.8085 0.070 Uiso 1 1 calc R . .
C13 C 0.1303(4) 0.2699(6) 0.5018(3) 0.0396(12) Uani 1 1 d . . .
H13A H 0.1417 0.2426 0.4542 0.048 Uiso 1 1 calc R . .
H13B H 0.1719 0.2051 0.5418 0.048 Uiso 1 1 calc R . .
C14 C 0.2261(4) 0.7431(6) 0.4214(3) 0.0363(12) Uani 1 1 d . . .
H14A H 0.2013 0.6418 0.4011 0.044 Uiso 1 1 calc R . .
H14B H 0.2882 0.7578 0.4133 0.044 Uiso 1 1 calc R . .
C15 C 0.1441(5) 0.8677(8) 0.2979(4) 0.0652(19) Uani 1 1 d . . .
H15A H 0.1002 0.9497 0.2741 0.098 Uiso 1 1 calc R . .
H15B H 0.1179 0.7692 0.2764 0.098 Uiso 1 1 calc R . .
H15C H 0.2050 0.8845 0.2892 0.098 Uiso 1 1 calc R . .
C16 C 0.3317(4) 0.5674(6) 0.7633(3) 0.0422(13) Uani 1 1 d . . .
H16A H 0.2628 0.5636 0.7558 0.051 Uiso 1 1 calc R . .
H16B H 0.3540 0.6719 0.7800 0.051 Uiso 1 1 calc R . .
C17 C 0.0279(4) 0.2363(6) 0.4952(3) 0.0460(14) Uani 1 1 d . . .
H17A H 0.0146 0.1280 0.4833 0.069 Uiso 1 1 calc R . .
H17B H -0.0137 0.2990 0.4552 0.069 Uiso 1 1 calc R . .
H17C H 0.0167 0.2601 0.5427 0.069 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cl3 2.4721(18) . ?
I1 Cl1 2.4937(14) . ?
I1 Cl6 2.5014(15) . ?
I1 Cl2 2.5136(17) . ?
N1 C5 1.518(5) . ?
N1 C3 1.521(5) . ?
N1 C4 1.523(5) . ?
N1 C2 1.529(5) . ?
C2 C7 1.514(6) . ?
C2 H2A 0.9500 . ?
C3 C9 1.515(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.513(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C14 1.505(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C15 1.494(8) . ?
C6 C14 1.521(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.507(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C16 1.514(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.519(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.523(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C17 1.516(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl3 I1 Cl1 88.76(5) . . ?
Cl3 I1 Cl6 91.19(6) . . ?
Cl1 I1 Cl6 178.14(6) . . ?
Cl3 I1 Cl2 177.61(6) . . ?
Cl1 I1 Cl2 89.79(5) . . ?
Cl6 I1 Cl2 90.33(6) . . ?
C5 N1 C3 106.3(3) . . ?
C5 N1 C4 111.3(3) . . ?
C3 N1 C4 110.8(3) . . ?
C5 N1 C2 111.8(3) . . ?
C3 N1 C2 111.1(3) . . ?
C4 N1 C2 105.6(3) . . ?
C7 C2 N1 116.6(3) . . ?
C7 C2 H2A 121.7 . . ?
N1 C2 H2A 121.7 . . ?
C9 C3 N1 116.4(3) . . ?
C9 C3 H3A 108.2 . . ?
N1 C3 H3A 108.2 . . ?
C9 C3 H3B 108.2 . . ?
N1 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
C11 C4 N1 116.0(4) . . ?
C11 C4 H4A 108.3 . . ?
N1 C4 H4A 108.3 . . ?
C11 C4 H4B 108.3 . . ?
N1 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C14 C5 N1 116.6(4) . . ?
C14 C5 H5A 108.1 . . ?
N1 C5 H5A 108.1 . . ?
C14 C5 H5B 108.1 . . ?
N1 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C15 C6 C14 112.8(5) . . ?
C15 C6 H6A 109.0 . . ?
C14 C6 H6A 109.0 . . ?
C15 C6 H6B 109.0 . . ?
C14 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C2 C7 C8 109.0(4) . . ?
C2 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
C2 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C10 C8 C7 113.0(4) . . ?
C10 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C10 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C16 C9 C3 109.9(4) . . ?
C16 C9 H9A 109.7 . . ?
C3 C9 H9A 109.7 . . ?
C16 C9 H9B 109.7 . . ?
C3 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 C13 110.5(4) . . ?
C4 C11 H11A 109.5 . . ?
C13 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C13 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C16 C12 H12A 109.5 . . ?
C16 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C16 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C17 C13 C11 112.6(4) . . ?
C17 C13 H13A 109.1 . . ?
C11 C13 H13A 109.1 . . ?
C17 C13 H13B 109.1 . . ?
C11 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C5 C14 C6 110.7(4) . . ?
C5 C14 H14A 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 C12 112.6(4) . . ?
C9 C16 H16A 109.1 . . ?
C12 C16 H16A 109.1 . . ?
C9 C16 H16B 109.1 . . ?
C12 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C7 63.0(5) . . . . ?
C3 N1 C2 C7 -55.5(5) . . . . ?
C4 N1 C2 C7 -175.7(4) . . . . ?
C5 N1 C3 C9 178.8(4) . . . . ?
C4 N1 C3 C9 57.7(5) . . . . ?
C2 N1 C3 C9 -59.3(5) . . . . ?
C5 N1 C4 C11 -56.5(5) . . . . ?
C3 N1 C4 C11 61.6(5) . . . . ?
C2 N1 C4 C11 -178.1(4) . . . . ?
C3 N1 C5 C14 -177.9(4) . . . . ?
C4 N1 C5 C14 -57.2(5) . . . . ?
C2 N1 C5 C14 60.7(5) . . . . ?
N1 C2 C7 C8 -179.2(4) . . . . ?
C2 C7 C8 C10 176.5(5) . . . . ?
N1 C3 C9 C16 -173.7(4) . . . . ?
N1 C4 C11 C13 -172.1(4) . . . . ?
C4 C11 C13 C17 -178.7(4) . . . . ?
N1 C5 C14 C6 174.8(4) . . . . ?
C15 C6 C14 C5 179.6(5) . . . . ?
C3 C9 C16 C12 178.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.651
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.105


