# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1906672'
loop_
_audit_author_name
_audit_author_address
'Ma Jian-ping'
;Shandong Normal University
China
;
_audit_update_record             
;
2019-03-30 deposited with the CCDC.	2019-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-03-15
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H38 I2 N2'
_chemical_formula_sum            'C28 H38 I2 N2'
_chemical_formula_weight         656.40
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.6628(3)
_cell_length_b                   17.8319(5)
_cell_length_c                   8.5916(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.541(3)
_cell_angle_gamma                90.00
_cell_volume                     1426.26(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2737
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      70.8330
_cell_measurement_theta_min      7.8740
_exptl_absorpt_coefficient_mu    17.429
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5003
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.02
_diffrn_reflns_theta_min         4.75
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9787
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00  56.00   1.00    1.00    --    0.00  57.00  90.00   26
  2  ω     37.00  69.00   1.00    1.00    --    0.00  57.00 120.00   32
  3  ω     26.00 123.00   1.00    1.00    --   54.00  77.00 150.00   97
  4  ω     32.00  68.00   1.00    1.00    --   54.00 -57.00 150.00   36
  5  ω     43.00 138.00   1.00    1.00    --  108.00 -77.00 120.00   95
  6  ω     83.00 110.00   1.00    1.00    --  108.00-111.00  90.00   27
  7  ω     69.00 102.00   1.00    1.00    --   54.00-125.00  30.00   33
  8  ω     47.00  84.00   1.00    1.00    --  108.00-111.00 120.00   37
  9  ω     38.00  77.00   1.00    1.00    --  108.00-111.00  90.00   39
 10  ω     -4.00  72.00   1.00    1.00    --   54.00 -57.00  30.00   76
 11  ω     92.00 140.00   1.00    1.00    --  108.00 -25.00 -90.00   48
 12  ω     85.00 111.00   1.00    1.00    --   54.00  57.00-150.00   26
 13  ω    112.00 175.00   1.00    1.00    --  108.00  77.00-120.00   63
 14  ω    103.00 153.00   1.00    1.00    --  108.00 111.00 -60.00   50
 15  ω     36.00 141.00   1.00    1.00    --  108.00 -25.00-180.00  105
 16  ω     89.00 114.00   1.00    1.00    --  108.00-111.00-180.00   25
 17  ω     38.00  63.00   1.00    1.00    --  108.00 -25.00 -90.00   25
 18  ω    -20.00   7.00   1.00    1.00    --    0.00  57.00 120.00   27
 19  ω    -14.00  13.00   1.00    1.00    --    0.00  57.00  90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0978980000
_diffrn_orient_matrix_UB_12      0.0697084000
_diffrn_orient_matrix_UB_13      0.0280966000
_diffrn_orient_matrix_UB_21      0.1333768000
_diffrn_orient_matrix_UB_22      -0.0509707000
_diffrn_orient_matrix_UB_23      0.0504182000
_diffrn_orient_matrix_UB_31      0.0068127000
_diffrn_orient_matrix_UB_32      -0.0034601000
_diffrn_orient_matrix_UB_33      -0.1767797000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2299
_reflns_number_total             2547
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         2.317
_refine_diff_density_min         -2.204
_refine_diff_density_rms         0.314
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0902
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1874P)²+0.3721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2424
_refine_ls_wR_factor_ref         0.2483
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
C1 C 0.4602(8) 0.0409(5) -0.2833(10) 0.0334(17) Uani 1 1 d . . .
H1A H 0.4283 0.0061 -0.2151 0.050 Uiso 1 1 calc R . .
H1B H 0.4526 0.0181 -0.3866 0.050 Uiso 1 1 calc R . .
H1C H 0.4015 0.0851 -0.2975 0.050 Uiso 1 1 calc R . .
C2 C 0.6166(7) 0.0621(4) -0.2052(8) 0.0217(13) Uani 1 1 d . . .
H2 H 0.6738 0.0160 -0.1902 0.026 Uiso 1 1 calc R . .
C3 C 0.6696(8) 0.1133(5) -0.3225(9) 0.0348(17) Uani 1 1 d . . .
H3A H 0.6088 0.1566 -0.3479 0.052 Uiso 1 1 calc R . .
H3B H 0.6665 0.0862 -0.4200 0.052 Uiso 1 1 calc R . .
H3C H 0.7665 0.1288 -0.2727 0.052 Uiso 1 1 calc R . .
C4 C 0.6414(7) 0.0996(3) -0.0427(8) 0.0178(13) Uani 1 1 d . . .
C5 C 0.5282(6) 0.1284(3) 0.0134(8) 0.0198(13) Uani 1 1 d . . .
H5 H 0.4343 0.1232 -0.0501 0.024 Uiso 1 1 calc R . .
C6 C 0.5536(7) 0.1647(3) 0.1621(9) 0.0216(14) Uani 1 1 d . . .
C7 C 0.6931(7) 0.1765(4) 0.2527(8) 0.0224(14) Uani 1 1 d . . .
H7 H 0.7102 0.2029 0.3493 0.027 Uiso 1 1 calc R . .
C8 C 0.8085(7) 0.1495(4) 0.2013(8) 0.0184(13) Uani 1 1 d . . .
C9 C 0.7818(7) 0.1075(3) 0.0575(8) 0.0176(13) Uani 1 1 d . . .
C10 C 0.9627(7) 0.1608(4) 0.3030(8) 0.0193(14) Uani 1 1 d . . .
H10 H 1.0253 0.1531 0.2315 0.023 Uiso 1 1 calc R . .
C11 C 1.0093(12) 0.1070(7) 0.4386(14) 0.062(3) Uani 1 1 d . . .
H11A H 0.9475 0.1114 0.5089 0.092 Uiso 1 1 calc R . .
H11B H 1.1063 0.1179 0.4979 0.092 Uiso 1 1 calc R . .
H11C H 1.0041 0.0569 0.3966 0.092 Uiso 1 1 calc R . .
C12 C 0.9871(10) 0.2418(5) 0.3670(16) 0.059(3) Uani 1 1 d . . .
H12A H 0.9449 0.2479 0.4554 0.088 Uiso 1 1 calc R . .
H12B H 0.9433 0.2762 0.2822 0.088 Uiso 1 1 calc R . .
H12C H 1.0883 0.2516 0.4035 0.088 Uiso 1 1 calc R . .
C13 C 0.9361(6) 0.0113(4) 0.0289(7) 0.0166(13) Uani 1 1 d . . .
C14 C 0.8685(8) -0.0467(4) 0.1122(10) 0.0283(16) Uani 1 1 d . . .
H14A H 0.7840 -0.0261 0.1346 0.042 Uiso 1 1 calc R . .
H14B H 0.9356 -0.0613 0.2116 0.042 Uiso 1 1 calc R . .
H14C H 0.8426 -0.0898 0.0435 0.042 Uiso 1 1 calc R . .
I1 I 0.37921(5) 0.20005(3) 0.24157(6) 0.0386(4) Uani 1 1 d . . .
N1 N 0.8983(5) 0.0802(3) 0.0056(6) 0.0185(11) 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 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.528(8) . ?
C2 H2 0.9800 . ?
C2 C3 1.545(11) . ?
C2 C4 1.507(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.405(9) . ?
C4 C9 1.406(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(10) . ?
C6 C7 1.380(9) . ?
C6 I1 2.078(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(10) . ?
C8 C9 1.408(9) . ?
C8 C10 1.526(9) . ?
C9 N1 1.404(8) . ?
C10 H10 0.9800 . ?
C10 C11 1.483(11) . ?
C10 C12 1.540(10) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C13 1.505(12) 3_755 ?
C13 C14 1.503(9) . ?
C13 N1 1.283(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2 107.8 . . ?
C1 C2 C3 108.7(6) . . ?
C3 C2 H2 107.8 . . ?
C4 C2 C1 114.2(5) . . ?
C4 C2 H2 107.8 . . ?
C4 C2 C3 110.2(6) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 122.3(6) . . ?
C5 C4 C9 117.7(6) . . ?
C9 C4 C2 120.0(6) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(5) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 I1 118.9(4) . . ?
C7 C6 C5 119.5(6) . . ?
C7 C6 I1 121.6(5) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.9(6) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 119.3(6) . . ?
C7 C8 C10 121.0(6) . . ?
C9 C8 C10 119.6(6) . . ?
C4 C9 C8 120.7(6) . . ?
N1 C9 C4 119.7(6) . . ?
N1 C9 C8 119.2(6) . . ?
C8 C10 H10 107.1 . . ?
C8 C10 C12 111.2(5) . . ?
C11 C10 C8 114.1(6) . . ?
C11 C10 H10 107.1 . . ?
C11 C10 C12 109.9(8) . . ?
C12 C10 H10 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C13 118.3(7) . 3_755 ?
N1 C13 C13 115.4(7) . 3_755 ?
N1 C13 C14 126.3(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 N1 C9 120.0(6) . . ?

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
C1 C2 C4 C5 -14.5(9) . . . . ?
C1 C2 C4 C9 166.4(6) . . . . ?
C2 C4 C5 C6 -178.2(6) . . . . ?
C2 C4 C9 C8 173.0(6) . . . . ?
C2 C4 C9 N1 -0.2(9) . . . . ?
C3 C2 C4 C5 108.2(7) . . . . ?
C3 C2 C4 C9 -70.9(8) . . . . ?
C4 C5 C6 C7 3.7(10) . . . . ?
C4 C5 C6 I1 -176.4(5) . . . . ?
C4 C9 N1 C13 -85.3(8) . . . . ?
C5 C4 C9 C8 -6.2(9) . . . . ?
C5 C4 C9 N1 -179.3(6) . . . . ?
C5 C6 C7 C8 -3.2(10) . . . . ?
C6 C7 C8 C9 -2.0(10) . . . . ?
C6 C7 C8 C10 -178.6(6) . . . . ?
C7 C8 C9 C4 6.8(10) . . . . ?
C7 C8 C9 N1 179.9(6) . . . . ?
C7 C8 C10 C11 80.1(9) . . . . ?
C7 C8 C10 C12 -44.9(10) . . . . ?
C8 C9 N1 C13 101.5(7) . . . . ?
C9 C4 C5 C6 0.9(9) . . . . ?
C9 C8 C10 C11 -96.5(10) . . . . ?
C9 C8 C10 C12 138.5(8) . . . . ?
C10 C8 C9 C4 -176.6(6) . . . . ?
C10 C8 C9 N1 -3.5(9) . . . . ?
C13 C13 N1 C9 -178.9(6) 3_755 . . . ?
C14 C13 N1 C9 -1.2(10) . . . . ?
I1 C6 C7 C8 177.0(5) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.892
_oxdiff_exptl_absorpt_empirical_full_min 0.365

