# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

####################################################################### 
# 
# 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_n3540
_database_code_depnum_ccdc_archive 'CCDC 1837582'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_audit_creation_date             2014-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H28 N, C H I3, Br'
_chemical_formula_sum            'C13 H29 Br I3 N'
_chemical_formula_weight         659.98
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   8.7748(6)
_cell_length_b                   8.9163(7)
_cell_length_c                   13.3043(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.065(3)
_cell_angle_gamma                90
_cell_volume                     1030.62(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.664
_cell_measurement_theta_min      2.759
_shelx_estimated_absorpt_T_max   0.782
_shelx_estimated_absorpt_T_min   0.243
_exptl_absorpt_coefficient_mu    6.477
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1254 before and 0.0869 after correction.
The Ratio of minimum to maximum transmission is 0.5746.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0893
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9213
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         2.621
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.776
_reflns_number_gt                5206
_reflns_number_total             5325
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         1.492
_refine_diff_density_min         -1.364
_refine_diff_density_rms         0.273
_refine_ls_abs_structure_details 
;
 Flack x determined using 2231 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0774P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1336
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B),
 C11(H11A,H11B), C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.08720(8) 0.41694(6) 0.50297(5) 0.01669(15) Uani 1 1 d . . . . .
I2 I -0.14496(7) 0.24603(6) 0.29680(5) 0.01727(16) Uani 1 1 d . . . . .
I3 I 0.26015(6) 0.26505(6) 0.29745(5) 0.01758(15) Uani 1 1 d . . . . .
C1 C 0.0767(14) 0.2432(10) 0.3889(8) 0.0184(19) Uani 1 1 d . . . . .
H1 H 0.0889 0.1443 0.4245 0.022 Uiso 1 1 calc R . . . .
Br1 Br 0.53255(12) 0.30816(11) 0.15348(9) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.5709(10) 0.7573(7) 0.3777(7) 0.0124(15) Uani 1 1 d . . . . .
C2 C 0.5212(12) 0.8742(10) 0.4507(7) 0.0170(16) Uani 1 1 d . . . . .
H2A H 0.5899 0.8648 0.5161 0.020 Uiso 1 1 calc R . . . .
H2B H 0.5389 0.9747 0.4230 0.020 Uiso 1 1 calc R . . . .
C3 C 0.3568(12) 0.8684(12) 0.4728(8) 0.0215(19) Uani 1 1 d . . . . .
H3A H 0.3349 0.7689 0.5005 0.026 Uiso 1 1 calc R . . . .
H3B H 0.2847 0.8849 0.4096 0.026 Uiso 1 1 calc R . . . .
C4 C 0.3365(14) 0.9902(12) 0.5496(9) 0.025(2) Uani 1 1 d . . . . .
H4A H 0.3501 1.0888 0.5194 0.037 Uiso 1 1 calc GR . . . .
H4B H 0.4134 0.9772 0.6099 0.037 Uiso 1 1 calc GR . . . .
H4C H 0.2331 0.9834 0.5690 0.037 Uiso 1 1 calc GR . . . .
C5 C 0.4734(12) 0.7687(10) 0.2732(8) 0.0161(17) Uani 1 1 d . . . . .
H5A H 0.4997 0.6834 0.2312 0.019 Uiso 1 1 calc R . . . .
H5B H 0.3637 0.7583 0.2819 0.019 Uiso 1 1 calc R . . . .
C6 C 0.4927(13) 0.9117(10) 0.2166(8) 0.0196(19) Uani 1 1 d . . . . .
H6A H 0.5957 0.9138 0.1944 0.024 Uiso 1 1 calc R . . . .
H6B H 0.4847 0.9987 0.2619 0.024 Uiso 1 1 calc R . . . .
C7 C 0.3670(15) 0.9224(13) 0.1233(9) 0.025(2) Uani 1 1 d . . . . .
H7A H 0.3807 1.0153 0.0862 0.037 Uiso 1 1 calc GR . . . .
H7B H 0.2653 0.9226 0.1457 0.037 Uiso 1 1 calc GR . . . .
H7C H 0.3753 0.8362 0.0787 0.037 Uiso 1 1 calc GR . . . .
C8 C 0.7387(11) 0.7908(10) 0.3717(7) 0.0146(15) Uani 1 1 d . . . . .
H8A H 0.7966 0.7820 0.4409 0.018 Uiso 1 1 calc R . . . .
H8B H 0.7466 0.8964 0.3501 0.018 Uiso 1 1 calc R . . . .
C9 C 0.8178(12) 0.6926(12) 0.3009(8) 0.0224(19) Uani 1 1 d . . . . .
H9A H 0.7626 0.6994 0.2308 0.027 Uiso 1 1 calc R . . . .
H9B H 0.8170 0.5866 0.3230 0.027 Uiso 1 1 calc R . . . .
C10 C 0.9834(16) 0.7471(13) 0.3038(11) 0.029(3) Uani 1 1 d . . . . .
H10A H 1.0396 0.6776 0.2652 0.044 Uiso 1 1 calc GR . . . .
H10B H 1.0335 0.7512 0.3743 0.044 Uiso 1 1 calc GR . . . .
H10C H 0.9833 0.8473 0.2736 0.044 Uiso 1 1 calc GR . . . .
C11 C 0.5457(13) 0.5991(11) 0.4142(7) 0.0187(18) Uani 1 1 d . . . . .
H11A H 0.5820 0.5274 0.3659 0.022 Uiso 1 1 calc R . . . .
H11B H 0.4338 0.5829 0.4127 0.022 Uiso 1 1 calc R . . . .
C12 C 0.6265(15) 0.5634(13) 0.5209(9) 0.026(2) Uani 1 1 d . . . . .
H12A H 0.7380 0.5843 0.5251 0.031 Uiso 1 1 calc R . . . .
H12B H 0.5843 0.6273 0.5712 0.031 Uiso 1 1 calc R . . . .
C13 C 0.6018(17) 0.4003(12) 0.5440(10) 0.030(3) Uani 1 1 d . . . . .
H13A H 0.6564 0.3375 0.5002 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.4916 0.3773 0.5315 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.6415 0.3800 0.6152 0.045 Uiso 1 1 calc GR . . . .


_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 C1 2.161(10) . ?
I2 C1 2.149(11) . ?
I3 C1 2.159(12) . ?
C1 H1 1.0000 . ?
N1 C2 1.529(12) . ?
N1 C5 1.530(13) . ?
N1 C8 1.516(13) . ?
N1 C11 1.518(12) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.512(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.519(14) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.503(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.544(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.523(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.528(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.528(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.508(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
I1 C1 H1 108.0 . . ?
I2 C1 I1 109.8(5) . . ?
I2 C1 I3 111.4(5) . . ?
I2 C1 H1 108.0 . . ?
I3 C1 I1 111.7(5) . . ?
I3 C1 H1 108.0 . . ?
C2 N1 C5 111.0(7) . . ?
C8 N1 C2 105.4(7) . . ?
C8 N1 C5 111.3(8) . . ?
C8 N1 C11 112.7(8) . . ?
C11 N1 C2 111.3(7) . . ?
C11 N1 C5 105.3(7) . . ?
N1 C2 H2A 107.9 . . ?
N1 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
C3 C2 N1 117.7(8) . . ?
C3 C2 H2A 107.9 . . ?
C3 C2 H2B 107.9 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
C2 C3 C4 108.1(9) . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 108.5 . . ?
N1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 N1 115.1(8) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C5 C6 C7 109.8(9) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 108.1 . . ?
N1 C8 H8B 108.1 . . ?
N1 C8 C9 116.7(8) . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
C8 C9 C10 108.4(9) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 108.5 . . ?
N1 C11 H11B 108.5 . . ?
N1 C11 C12 114.9(8) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 C11 109.2(10) . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
N1 C2 C3 C4 177.9(8) . . . . ?
N1 C5 C6 C7 -169.1(9) . . . . ?
N1 C8 C9 C10 178.5(9) . . . . ?
N1 C11 C12 C13 -175.7(10) . . . . ?
C2 N1 C5 C6 65.6(11) . . . . ?
C2 N1 C8 C9 -178.4(8) . . . . ?
C2 N1 C11 C12 -56.7(12) . . . . ?
C5 N1 C2 C3 59.9(11) . . . . ?
C5 N1 C8 C9 -57.9(10) . . . . ?
C5 N1 C11 C12 -177.1(9) . . . . ?
C8 N1 C2 C3 -179.6(9) . . . . ?
C8 N1 C5 C6 -51.5(11) . . . . ?
C8 N1 C11 C12 61.4(11) . . . . ?
C11 N1 C2 C3 -57.1(11) . . . . ?
C11 N1 C5 C6 -173.9(9) . . . . ?
C11 N1 C8 C9 60.1(11) . . . . ?

####################################################################### 
# 
# 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_n3542
_database_code_depnum_ccdc_archive 'CCDC 1837583'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_audit_creation_date             2014-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H28 N, C H I3, Cl'
_chemical_formula_sum            'C13 H29 Cl I3 N'
_chemical_formula_weight         615.52
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   8.7174(5)
_cell_length_b                   8.8068(5)
_cell_length_c                   13.2169(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.763(3)
_cell_angle_gamma                90
_cell_volume                     1005.39(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.424
_cell_measurement_theta_min      2.312
_shelx_estimated_absorpt_T_max   0.731
_shelx_estimated_absorpt_T_min   0.191
_exptl_absorpt_coefficient_mu    4.785
_exptl_absorpt_correction_T_max  0.7285
_exptl_absorpt_correction_T_min  0.6230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1182 before and 0.0970 after correction.
The Ratio of minimum to maximum transmission is 0.8552.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24409
_diffrn_reflns_point_group_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.336
_diffrn_reflns_theta_min         2.644
_diffrn_ambient_temperature      99.86
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.848
_reflns_Friedel_fraction_max     0.849
_reflns_number_gt                3228
_reflns_number_total             3359
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details 
;
 Flack x determined using 1451 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3359
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0614
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B),
 C11(H11A,H11B), C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.26836(8) 0.76082(6) 0.28736(5) 0.01746(17) Uani 1 1 d . . . . .
I2 I 0.49973(8) 0.92844(6) 0.49857(5) 0.01722(17) Uani 1 1 d . . . . .
I3 I 0.67793(7) 0.78010(6) 0.29082(4) 0.01789(17) Uani 1 1 d . . . . .
C1 C 0.4919(15) 0.7581(10) 0.3815(7) 0.022(3) Uani 1 1 d . . . . .
H1 H 0.5033 0.6571 0.4162 0.026 Uiso 1 1 calc R . . . .
Cl1 Cl -0.0501(3) 0.8160(3) 0.15474(18) 0.0227(6) Uani 1 1 d . . . . .
N1 N -0.0077(10) 0.2666(7) 0.3719(6) 0.0106(18) Uani 1 1 d . . . . .
C2 C -0.1053(15) 0.2768(10) 0.2657(8) 0.020(3) Uani 1 1 d . . . . .
H2A H -0.0727 0.1947 0.2221 0.024 Uiso 1 1 calc R . . . .
H2B H -0.2153 0.2591 0.2733 0.024 Uiso 1 1 calc R . . . .
C3 C -0.0922(13) 0.4259(10) 0.2127(6) 0.019(2) Uani 1 1 d . . . . .
H3A H 0.0135 0.4370 0.1941 0.022 Uiso 1 1 calc R . . . .
H3B H -0.1100 0.5100 0.2595 0.022 Uiso 1 1 calc R . . . .
C4 C -0.2102(14) 0.4355(10) 0.1166(7) 0.023(3) Uani 1 1 d . . . . .
H4A H -0.1925 0.5285 0.0791 0.035 Uiso 1 1 calc GR . . . .
H4B H -0.3149 0.4373 0.1357 0.035 Uiso 1 1 calc GR . . . .
H4C H -0.1989 0.3470 0.0733 0.035 Uiso 1 1 calc GR . . . .
C5 C 0.1619(12) 0.3031(10) 0.3657(7) 0.016(2) Uani 1 1 d . . . . .
H5A H 0.2213 0.2878 0.4342 0.019 Uiso 1 1 calc R . . . .
H5B H 0.1696 0.4120 0.3485 0.019 Uiso 1 1 calc R . . . .
C6 C 0.2393(13) 0.2108(10) 0.2887(8) 0.020(2) Uani 1 1 d . . . . .
H6A H 0.1863 0.2283 0.2186 0.024 Uiso 1 1 calc R . . . .
H6B H 0.2350 0.1011 0.3042 0.024 Uiso 1 1 calc R . . . .
C7 C 0.4085(14) 0.2649(11) 0.2981(8) 0.022(3) Uani 1 1 d . . . . .
H7A H 0.4559 0.2274 0.2398 0.033 Uiso 1 1 calc GR . . . .
H7B H 0.4660 0.2257 0.3616 0.033 Uiso 1 1 calc GR . . . .
H7C H 0.4115 0.3762 0.2990 0.033 Uiso 1 1 calc GR . . . .
C8 C -0.0275(13) 0.1026(9) 0.4075(6) 0.016(2) Uani 1 1 d . . . . .
H8A H -0.1395 0.0801 0.4022 0.019 Uiso 1 1 calc R . . . .
H8B H 0.0174 0.0332 0.3604 0.019 Uiso 1 1 calc R . . . .
C9 C 0.0464(13) 0.0681(10) 0.5157(7) 0.021(3) Uani 1 1 d . . . . .
H9A H 0.1580 0.0933 0.5234 0.025 Uiso 1 1 calc R . . . .
H9B H -0.0026 0.1308 0.5646 0.025 Uiso 1 1 calc R . . . .
C10 C 0.0258(16) -0.0988(11) 0.5385(8) 0.031(3) Uani 1 1 d . . . . .
H10A H 0.0704 -0.1605 0.4881 0.046 Uiso 1 1 calc GR . . . .
H10B H -0.0848 -0.1218 0.5351 0.046 Uiso 1 1 calc GR . . . .
H10C H 0.0784 -0.1221 0.6070 0.046 Uiso 1 1 calc GR . . . .
C11 C -0.0590(13) 0.3799(10) 0.4469(7) 0.017(2) Uani 1 1 d . . . . .
H11A H 0.0072 0.3662 0.5133 0.021 Uiso 1 1 calc R . . . .
H11B H -0.0393 0.4833 0.4222 0.021 Uiso 1 1 calc R . . . .
C12 C -0.2243(13) 0.3715(11) 0.4649(7) 0.022(2) Uani 1 1 d . . . . .
H12A H -0.2464 0.2699 0.4917 0.026 Uiso 1 1 calc R . . . .
H12B H -0.2932 0.3874 0.3999 0.026 Uiso 1 1 calc R . . . .
C13 C -0.2542(15) 0.4928(12) 0.5414(8) 0.025(3) Uani 1 1 d . . . . .
H13A H -0.2459 0.5933 0.5108 0.038 Uiso 1 1 calc GR . . . .
H13B H -0.1776 0.4838 0.6025 0.038 Uiso 1 1 calc GR . . . .
H13C H -0.3584 0.4796 0.5601 0.038 Uiso 1 1 calc GR . . . .


_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 C1 2.166(12) . ?
I2 C1 2.149(9) . ?
I3 C1 2.152(12) . ?
C1 H1 1.0000 . ?
N1 C2 1.543(13) . ?
N1 C5 1.526(13) . ?
N1 C8 1.536(10) . ?
N1 C11 1.515(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.501(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.524(15) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.528(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.539(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.517(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.516(12) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.494(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.517(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
I1 C1 H1 107.4 . . ?
I2 C1 I1 110.2(5) . . ?
I2 C1 I3 112.7(5) . . ?
I2 C1 H1 107.4 . . ?
I3 C1 I1 111.5(4) . . ?
I3 C1 H1 107.4 . . ?
C5 N1 C2 111.0(7) . . ?
C5 N1 C8 111.4(7) . . ?
C8 N1 C2 105.2(6) . . ?
C11 N1 C2 112.4(7) . . ?
C11 N1 C5 105.7(7) . . ?
C11 N1 C8 111.3(6) . . ?
N1 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 N1 114.1(8) . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 C4 110.6(8) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 108.2 . . ?
N1 C5 H5B 108.2 . . ?
N1 C5 C6 116.3(8) . . ?
H5A C5 H5B 107.4 . . ?
C6 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C5 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
C5 C6 C7 106.6(8) . . ?
H6A C6 H6B 108.6 . . ?
C7 C6 H6A 110.4 . . ?
C7 C6 H6B 110.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 108.5 . . ?
N1 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 N1 115.2(7) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 C8 109.6(8) . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 108.1 . . ?
N1 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 N1 116.6(8) . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C11 C12 C13 109.1(9) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
N1 C2 C3 C4 -171.2(8) . . . . ?
N1 C5 C6 C7 -178.7(8) . . . . ?
N1 C8 C9 C10 -176.9(8) . . . . ?
N1 C11 C12 C13 -179.9(8) . . . . ?
C2 N1 C5 C6 -53.9(10) . . . . ?
C2 N1 C8 C9 -174.4(9) . . . . ?
C2 N1 C11 C12 57.2(10) . . . . ?
C5 N1 C2 C3 -54.8(10) . . . . ?
C5 N1 C8 C9 65.2(10) . . . . ?
C5 N1 C11 C12 178.3(8) . . . . ?
C8 N1 C2 C3 -175.4(8) . . . . ?
C8 N1 C5 C6 63.0(10) . . . . ?
C8 N1 C11 C12 -60.6(11) . . . . ?
C11 N1 C2 C3 63.3(11) . . . . ?
C11 N1 C5 C6 -176.0(8) . . . . ?
C11 N1 C8 C9 -52.4(11) . . . . ?

####################################################################### 
# 
# 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_RS2_0m
_database_code_depnum_ccdc_archive 'CCDC 1837584'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, C H I3, I'
_chemical_formula_sum            'C17 H37 I4 N'
_chemical_formula_weight         763.07

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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   15.9191(6)
_cell_length_b                   17.5775(7)
_cell_length_c                   17.8152(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4985.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9017
_cell_measurement_theta_min      2.8653
_cell_measurement_theta_max      36.2966

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_F_000             2864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    5.000
_shelx_estimated_absorpt_T_min   0.177
_shelx_estimated_absorpt_T_max   0.563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4089
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube X-ray source'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67764
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.809
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7607
_reflns_number_gt                6492
_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       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_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)+43.3708P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00035(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7607
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_restrained_S_all      1.295
_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
C1 C 0.6651(3) 0.1130(2) 0.7175(2) 0.0153(8) Uani 1 1 d . . . . .
H1 H 0.603073 0.103764 0.716910 0.018 Uiso 1 1 calc R U . . .
C2 C 0.9633(3) 0.2544(2) 0.4379(3) 0.0140(7) Uani 1 1 d . . . . .
H2A H 0.966340 0.246448 0.382952 0.017 Uiso 1 1 calc R U . . .
H2B H 1.021069 0.249709 0.458002 0.017 Uiso 1 1 calc R U . . .
C3 C 0.9321(3) 0.3349(2) 0.4527(3) 0.0159(8) Uani 1 1 d . . . . .
H3A H 0.871937 0.338477 0.439177 0.019 Uiso 1 1 calc R U . . .
H3B H 0.937732 0.346658 0.506763 0.019 Uiso 1 1 calc R U . . .
C4 C 0.9820(3) 0.3925(2) 0.4071(3) 0.0199(9) Uani 1 1 d . . . . .
H4A H 1.040580 0.394276 0.425710 0.024 Uiso 1 1 calc R U . . .
H4B H 0.983356 0.376525 0.353824 0.024 Uiso 1 1 calc R U . . .
C5 C 0.9432(3) 0.4712(3) 0.4129(3) 0.0241(10) Uani 1 1 d . . . . .
H5A H 0.979537 0.508263 0.387738 0.036 Uiso 1 1 calc R U . . .
H5B H 0.937015 0.485118 0.465867 0.036 Uiso 1 1 calc R U . . .
H5C H 0.887815 0.471013 0.388777 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8966(3) 0.2047(2) 0.5556(2) 0.0146(8) Uani 1 1 d . . . . .
H6A H 0.860770 0.250320 0.561922 0.017 Uiso 1 1 calc R U . . .
H6B H 0.865212 0.160792 0.576240 0.017 Uiso 1 1 calc R U . . .
C7 C 0.9758(3) 0.2156(3) 0.6020(2) 0.0182(8) Uani 1 1 d . . . . .
H7A H 1.010701 0.256367 0.579726 0.022 Uiso 1 1 calc R U . . .
H7B H 1.009078 0.167958 0.602065 0.022 Uiso 1 1 calc R U . . .
C8 C 0.9516(3) 0.2369(3) 0.6830(3) 0.0225(9) Uani 1 1 d . . . . .
H8A H 0.909310 0.200142 0.701540 0.027 Uiso 1 1 calc R U . . .
H8B H 1.001877 0.232588 0.715341 0.027 Uiso 1 1 calc R U . . .
C9 C 0.9161(4) 0.3168(3) 0.6900(3) 0.0284(11) Uani 1 1 d . . . . .
H9A H 0.958039 0.353762 0.672890 0.043 Uiso 1 1 calc R U . . .
H9B H 0.901968 0.327017 0.742623 0.043 Uiso 1 1 calc R U . . .
H9C H 0.865394 0.321282 0.659141 0.043 Uiso 1 1 calc R U . . .
C10 C 0.9531(3) 0.1155(2) 0.4607(2) 0.0136(7) Uani 1 1 d . . . . .
H10A H 1.007927 0.116937 0.486882 0.016 Uiso 1 1 calc R U . . .
H10B H 0.918725 0.075440 0.484807 0.016 Uiso 1 1 calc R U . . .
C11 C 0.9681(3) 0.0932(2) 0.3797(2) 0.0157(8) Uani 1 1 d . . . . .
H11A H 1.006744 0.130164 0.355901 0.019 Uiso 1 1 calc R U . . .
H11B H 0.914305 0.094202 0.351862 0.019 Uiso 1 1 calc R U . . .
C12 C 1.0063(3) 0.0133(2) 0.3755(3) 0.0165(8) Uani 1 1 d . . . . .
H12A H 1.058293 0.011580 0.405882 0.020 Uiso 1 1 calc R U . . .
H12B H 0.966187 -0.023982 0.396831 0.020 Uiso 1 1 calc R U . . .
C13 C 1.0265(3) -0.0086(3) 0.2946(3) 0.0221(9) Uani 1 1 d . . . . .
H13A H 0.976148 -0.002445 0.263508 0.033 Uiso 1 1 calc R U . . .
H13B H 1.045062 -0.061693 0.292832 0.033 Uiso 1 1 calc R U . . .
H13C H 1.071267 0.024419 0.275445 0.033 Uiso 1 1 calc R U . . .
C14 C 0.8238(2) 0.1930(2) 0.4339(2) 0.0130(7) Uani 1 1 d . . . . .
H14A H 0.795777 0.241495 0.447038 0.016 Uiso 1 1 calc R U . . .
H14B H 0.832402 0.192848 0.378847 0.016 Uiso 1 1 calc R U . . .
C15 C 0.7648(3) 0.1278(3) 0.4539(2) 0.0169(8) Uani 1 1 d . . . . .
H15A H 0.760400 0.122989 0.509102 0.020 Uiso 1 1 calc R U . . .
H15B H 0.787158 0.079387 0.433671 0.020 Uiso 1 1 calc R U . . .
C16 C 0.6779(3) 0.1436(3) 0.4204(3) 0.0242(10) Uani 1 1 d . . . . .
H16A H 0.636877 0.107558 0.442322 0.029 Uiso 1 1 calc R U . . .
H16B H 0.660262 0.195697 0.434380 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6760(4) 0.1361(3) 0.3351(4) 0.0341(13) Uani 1 1 d . . . . .
H17A H 0.708993 0.177276 0.312562 0.051 Uiso 1 1 calc R U . . .
H17B H 0.617809 0.139259 0.317412 0.051 Uiso 1 1 calc R U . . .
H17C H 0.700018 0.086947 0.320438 0.051 Uiso 1 1 calc R U . . .
N1 N 0.9097(2) 0.19147(19) 0.4718(2) 0.0114(6) Uani 1 1 d . . . . .
I1 I 0.68298(2) 0.21928(2) 0.65904(2) 0.01393(7) Uani 1 1 d . . . . .
I2 I 0.69937(2) 0.11678(2) 0.83452(2) 0.01613(7) Uani 1 1 d . . . . .
I3 I 0.71917(2) 0.01913(2) 0.65616(2) 0.01690(7) Uani 1 1 d . . . . .
I4 I 0.79686(2) -0.12519(2) 0.53608(2) 0.01533(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 I2 2.156(4) . ?
C1 I3 2.158(4) . ?
C1 I1 2.159(4) . ?
C1 H1 1.0000 . ?
C2 N1 1.522(5) . ?
C2 C3 1.522(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.522(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.518(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.520(6) . ?
C6 N1 1.525(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.540(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.519(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.514(6) . ?
C10 N1 1.517(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.532(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.526(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.525(6) . ?
C14 N1 1.525(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.532(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.526(8) . ?
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
I2 C1 I3 114.36(19) . . ?
I2 C1 I1 113.96(19) . . ?
I3 C1 I1 111.38(19) . . ?
I2 C1 H1 105.4 . . ?
I3 C1 H1 105.4 . . ?
I1 C1 H1 105.4 . . ?
N1 C2 C3 115.1(3) . . ?
N1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
N1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C2 110.9(4) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 111.0(4) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
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 . . ?
C7 C6 N1 115.9(3) . . ?
C7 C6 H6A 108.3 . . ?
N1 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
N1 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C6 C7 C8 109.4(4) . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 113.4(4) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 115.1(3) . . ?
C11 C10 H10A 108.5 . . ?
N1 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
N1 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 110.3(3) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 111.1(4) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N1 115.8(3) . . ?
C15 C14 H14A 108.3 . . ?
N1 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
N1 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 C16 109.2(4) . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C17 C16 C15 113.0(4) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 N1 C2 109.4(3) . . ?
C10 N1 C6 108.9(3) . . ?
C2 N1 C6 110.8(3) . . ?
C10 N1 C14 111.5(3) . . ?
C2 N1 C14 108.3(3) . . ?
C6 N1 C14 107.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -171.5(4) . . . . ?
C2 C3 C4 C5 171.8(4) . . . . ?
N1 C6 C7 C8 173.8(4) . . . . ?
C6 C7 C8 C9 -71.2(5) . . . . ?
N1 C10 C11 C12 -175.9(3) . . . . ?
C10 C11 C12 C13 -176.8(4) . . . . ?
N1 C14 C15 C16 172.1(4) . . . . ?
C14 C15 C16 C17 70.9(5) . . . . ?
C11 C10 N1 C2 -60.6(5) . . . . ?
C11 C10 N1 C6 178.2(4) . . . . ?
C11 C10 N1 C14 59.2(5) . . . . ?
C3 C2 N1 C10 -173.4(4) . . . . ?
C3 C2 N1 C6 -53.3(5) . . . . ?
C3 C2 N1 C14 64.8(5) . . . . ?
C7 C6 N1 C10 66.5(4) . . . . ?
C7 C6 N1 C2 -53.8(5) . . . . ?
C7 C6 N1 C14 -172.3(4) . . . . ?
C15 C14 N1 C10 52.4(5) . . . . ?
C15 C14 N1 C2 172.9(3) . . . . ?
C15 C14 N1 C6 -67.2(4) . . . . ?

_refine_diff_density_max         1.900
_refine_diff_density_min         -1.572
_refine_diff_density_rms         0.227

