# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1057046'
_audit_update_record             
;
2015-10-17 deposited with the CCDC.
2016-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Cl2 I N'
_chemical_formula_weight         446.13

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   20.9498(7)
_cell_length_b                   12.8783(4)
_cell_length_c                   16.4392(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.777(2)
_cell_angle_gamma                90.00
_cell_volume                     3686.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6063
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      23.56

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    2.023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6334
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13189
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         23.82
_reflns_number_total             2818
_reflns_number_gt                2204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0330P)²+9.4687P] 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         2818
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.003
_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 1.147214(18) 0.12044(3) 1.09274(2) 0.08014(16) Uani 1 1 d . . .
Cl1 Cl 0.90948(7) 0.53004(10) 0.62694(10) 0.0822(4) Uani 1 1 d . . .
Cl2 Cl 0.81519(9) 0.69065(10) 0.66649(11) 0.0958(4) Uani 1 1 d . . .
N1 N 0.92629(17) 0.1935(2) 0.8194(2) 0.0473(7) Uani 1 1 d . . .
C1 C 0.8872(2) 0.2654(3) 0.8479(3) 0.0493(9) Uani 1 1 d . . .
H1A H 0.8403 0.2336 0.8360 0.059 Uiso 1 1 calc R . .
C2 C 0.9548(2) 0.2514(3) 0.9574(3) 0.0514(10) Uani 1 1 d . . .
C3 C 0.9846(2) 0.1643(3) 0.9218(3) 0.0473(9) Uani 1 1 d . . .
H3A H 0.9732 0.0957 0.9367 0.057 Uiso 1 1 calc R . .
C4 C 0.8859(2) 0.1221(3) 0.7426(3) 0.0464(9) Uani 1 1 d . . .
C5 C 0.9151(3) 0.0240(3) 0.7483(3) 0.0583(11) Uani 1 1 d . . .
H5A H 0.9614 0.0038 0.8044 0.070 Uiso 1 1 calc R . .
C6 C 0.8752(3) -0.0442(4) 0.6702(4) 0.0716(13) Uani 1 1 d . . .
H6A H 0.8953 -0.1098 0.6744 0.086 Uiso 1 1 calc R . .
C7 C 0.8075(3) -0.0167(4) 0.5878(4) 0.0800(15) Uani 1 1 d . . .
H7A H 0.7811 -0.0634 0.5362 0.096 Uiso 1 1 calc R . .
C8 C 0.7781(3) 0.0806(5) 0.5812(3) 0.0749(13) Uani 1 1 d . . .
H8A H 0.7316 0.0998 0.5248 0.090 Uiso 1 1 calc R . .
C9 C 0.8171(2) 0.1504(3) 0.6581(3) 0.0592(11) Uani 1 1 d . . .
H9A H 0.7969 0.2162 0.6529 0.071 Uiso 1 1 calc R . .
C10 C 0.8944(2) 0.4008(3) 0.7430(3) 0.0532(10) Uani 1 1 d . . .
H10A H 0.9222 0.3542 0.7310 0.064 Uiso 1 1 calc R . .
C11 C 0.8702(2) 0.3713(3) 0.8023(3) 0.0493(9) Uani 1 1 d . . .
C12 C 0.8283(2) 0.4428(3) 0.8183(3) 0.0606(11) Uani 1 1 d . . .
H12A H 0.8104 0.4242 0.8569 0.073 Uiso 1 1 calc R . .
C13 C 0.8130(2) 0.5402(4) 0.7778(3) 0.0658(12) Uani 1 1 d . . .
H13A H 0.7861 0.5875 0.7905 0.079 Uiso 1 1 calc R . .
C14 C 0.8371(2) 0.5679(3) 0.7190(3) 0.0608(11) Uani 1 1 d . . .
C15 C 0.8781(2) 0.4987(3) 0.7012(3) 0.0547(10) Uani 1 1 d . . .
C18 C 1.0062(3) 0.3463(3) 1.0029(3) 0.0727(13) Uani 1 1 d . . .
H18A H 1.0220 0.3698 0.9612 0.109 Uiso 1 1 calc R . .
H18B H 1.0507 0.3283 1.0659 0.109 Uiso 1 1 calc R . .
H18C H 0.9784 0.4006 1.0101 0.109 Uiso 1 1 calc R . .
C19 C 0.9290(3) 0.2116(4) 1.0224(4) 0.0794(14) Uani 1 1 d . . .
H19A H 0.9728 0.2044 1.0884 0.119 Uiso 1 1 calc R . .
H19B H 0.9044 0.1453 0.9988 0.119 Uiso 1 1 calc R . .
H19C H 0.8934 0.2600 1.0208 0.119 Uiso 1 1 calc R . .
C20 C 1.0645(2) 0.1673(4) 0.9442(3) 0.0599(11) Uani 1 1 d . . .
H20A H 1.0761 0.2372 0.9342 0.072 Uiso 1 1 calc R . .
H20B H 1.0677 0.1213 0.8999 0.072 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 C20 2.150(4) . ?
Cl1 C15 1.726(4) . ?
Cl2 C14 1.736(5) . ?
N1 C4 1.403(5) . ?
N1 C1 1.473(5) . ?
N1 C3 1.476(5) . ?
C1 C11 1.501(5) . ?
C1 C2 1.564(5) . ?
C1 H1A 0.9800 . ?
C2 C18 1.522(6) . ?
C2 C19 1.530(5) . ?
C2 C3 1.548(5) . ?
C3 C20 1.502(5) . ?
C3 H3A 0.9800 . ?
C4 C5 1.384(5) . ?
C4 C9 1.384(6) . ?
C5 C6 1.388(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.355(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.374(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.387(6) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 C11 1.379(5) . ?
C10 C15 1.385(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.394(5) . ?
C12 C13 1.372(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.364(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.377(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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 122.3(3) . . ?
C4 N1 C3 124.2(3) . . ?
C1 N1 C3 93.0(3) . . ?
N1 C1 C11 115.7(3) . . ?
N1 C1 C2 89.2(3) . . ?
C11 C1 C2 119.5(3) . . ?
N1 C1 H1A 110.3 . . ?
C11 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
C18 C2 C19 110.8(3) . . ?
C18 C2 C3 116.3(3) . . ?
C19 C2 C3 113.3(3) . . ?
C18 C2 C1 114.4(3) . . ?
C19 C2 C1 113.5(3) . . ?
C3 C2 C1 86.8(3) . . ?
N1 C3 C20 112.1(3) . . ?
N1 C3 C2 89.7(3) . . ?
C20 C3 C2 121.1(3) . . ?
N1 C3 H3A 110.7 . . ?
C20 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C5 C4 C9 118.9(4) . . ?
C5 C4 N1 121.0(4) . . ?
C9 C4 N1 120.1(4) . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C7 C6 C5 121.1(5) . . ?
C7 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
C6 C7 C8 119.4(4) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C7 C8 C9 120.5(5) . . ?
C7 C8 H8A 119.7 . . ?
C9 C8 H8A 119.7 . . ?
C4 C9 C8 120.1(4) . . ?
C4 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C11 C10 C15 121.0(4) . . ?
C11 C10 H10A 119.5 . . ?
C15 C10 H10A 119.5 . . ?
C10 C11 C12 118.0(4) . . ?
C10 C11 C1 121.6(3) . . ?
C12 C11 C1 120.4(3) . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C14 C13 C12 120.4(4) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 120.1(4) . . ?
C13 C14 Cl2 119.4(3) . . ?
C15 C14 Cl2 120.5(4) . . ?
C14 C15 C10 119.7(4) . . ?
C14 C15 Cl1 121.8(3) . . ?
C10 C15 Cl1 118.6(3) . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 I1 110.9(2) . . ?
C3 C20 H20A 109.5 . . ?
I1 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
I1 C20 H20B 109.5 . . ?
H20A C20 H20B 108.0 . . ?

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 N1 C1 C11 -94.3(4) . . . . ?
C3 N1 C1 C11 131.4(3) . . . . ?
C4 N1 C1 C2 143.0(3) . . . . ?
C3 N1 C1 C2 8.7(3) . . . . ?
N1 C1 C2 C18 109.2(4) . . . . ?
C11 C1 C2 C18 -10.1(5) . . . . ?
N1 C1 C2 C19 -122.4(3) . . . . ?
C11 C1 C2 C19 118.3(4) . . . . ?
N1 C1 C2 C3 -8.3(3) . . . . ?
C11 C1 C2 C3 -127.7(3) . . . . ?
C4 N1 C3 C20 94.4(4) . . . . ?
C1 N1 C3 C20 -132.6(3) . . . . ?
C4 N1 C3 C2 -141.9(3) . . . . ?
C1 N1 C3 C2 -8.8(3) . . . . ?
C18 C2 C3 N1 -107.4(4) . . . . ?
C19 C2 C3 N1 122.5(4) . . . . ?
C1 C2 C3 N1 8.3(3) . . . . ?
C18 C2 C3 C20 8.5(5) . . . . ?
C19 C2 C3 C20 -121.6(4) . . . . ?
C1 C2 C3 C20 124.2(4) . . . . ?
C1 N1 C4 C5 -143.1(4) . . . . ?
C3 N1 C4 C5 -22.8(5) . . . . ?
C1 N1 C4 C9 39.0(5) . . . . ?
C3 N1 C4 C9 159.2(3) . . . . ?
C9 C4 C5 C6 -0.2(6) . . . . ?
N1 C4 C5 C6 -178.1(3) . . . . ?
C4 C5 C6 C7 -0.3(6) . . . . ?
C5 C6 C7 C8 0.5(7) . . . . ?
C6 C7 C8 C9 -0.1(7) . . . . ?
C5 C4 C9 C8 0.5(6) . . . . ?
N1 C4 C9 C8 178.5(4) . . . . ?
C7 C8 C9 C4 -0.4(6) . . . . ?
C15 C10 C11 C12 0.4(6) . . . . ?
C15 C10 C11 C1 179.8(4) . . . . ?
N1 C1 C11 C10 -4.3(5) . . . . ?
C2 C1 C11 C10 100.4(4) . . . . ?
N1 C1 C11 C12 175.1(3) . . . . ?
C2 C1 C11 C12 -80.1(4) . . . . ?
C10 C11 C12 C13 -1.2(6) . . . . ?
C1 C11 C12 C13 179.3(4) . . . . ?
C11 C12 C13 C14 1.6(6) . . . . ?
C12 C13 C14 C15 -1.0(6) . . . . ?
C12 C13 C14 Cl2 178.6(3) . . . . ?
C13 C14 C15 C10 0.2(6) . . . . ?
Cl2 C14 C15 C10 -179.4(3) . . . . ?
C13 C14 C15 Cl1 179.7(3) . . . . ?
Cl2 C14 C15 Cl1 0.1(5) . . . . ?
C11 C10 C15 C14 0.1(6) . . . . ?
C11 C10 C15 Cl1 -179.4(3) . . . . ?
N1 C3 C20 I1 -178.5(2) . . . . ?
C2 C3 C20 I1 77.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        23.82
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.055
