# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_14028
_database_code_depnum_ccdc_archive 'CCDC 1036695'
_audit_update_record             
;
2014-11-28 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_vrf_PLAT431_I                   
;
PROBLEM: Short Inter HL..A  Contact I1     ..  O3      ..       2.97 Ang.  
RESPONSE: ...This short distance is due to halogen bonding between I and
O atom.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 I O4'
_chemical_formula_sum            'C20 H21 I O4'
_chemical_formula_weight         452.27

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'
O O 0.0106 0.0060 '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                   15.062(3)
_cell_length_b                   8.1555(15)
_cell_length_c                   15.606(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.717(4)
_cell_angle_gamma                90.00
_cell_volume                     1854.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    581
_cell_measurement_theta_min      2.699
_cell_measurement_theta_max      23.162

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    1.748
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   
;
absorption correction based on 3380 reflections(SADABS);Rint 0.0770 before
correction and 0.0519 after.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker Apex 2000 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            14049
_diffrn_reflns_av_R_equivalents  0.1203
_diffrn_reflns_av_sigmaI/netI    0.1256
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3635
_reflns_number_gt                2501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0156P)²+0.0000P] 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         3635
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.869
_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 0.06465(2) -0.02700(4) 0.16228(3) 0.02392(12) Uani 1 1 d . . .
O1 O -0.1152(2) -0.0979(4) 0.1501(2) 0.0251(10) Uani 1 1 d . . .
H1 H -0.1340 -0.0908 0.0948 0.038 Uiso 1 1 calc R . .
O2 O 0.1624(3) 0.0864(5) 0.0256(3) 0.0368(11) Uani 1 1 d . . .
O3 O 0.3203(3) 0.1737(5) 0.2913(3) 0.0309(10) Uani 1 1 d . . .
O4 O 0.1889(3) 0.1063(5) 0.3250(3) 0.0328(11) Uani 1 1 d . . .
C1 C -0.0143(4) 0.1931(7) 0.1442(4) 0.0237(14) Uani 1 1 d . . .
C2 C 0.0257(4) 0.3329(7) 0.1187(4) 0.0261(15) Uani 1 1 d . . .
H2 H 0.0844 0.3272 0.1067 0.031 Uiso 1 1 calc R . .
C3 C -0.0208(4) 0.4789(8) 0.1111(4) 0.0338(16) Uani 1 1 d . . .
H3 H 0.0060 0.5749 0.0941 0.041 Uiso 1 1 calc R . .
C4 C -0.1059(4) 0.4874(7) 0.1278(4) 0.0335(16) Uani 1 1 d . . .
H4 H -0.1378 0.5889 0.1222 0.040 Uiso 1 1 calc R . .
C5 C -0.1446(4) 0.3492(7) 0.1525(4) 0.0290(15) Uani 1 1 d . . .
H5 H -0.2032 0.3570 0.1645 0.035 Uiso 1 1 calc R . .
C6 C -0.1001(4) 0.1956(7) 0.1607(3) 0.0205(13) Uani 1 1 d . . .
C7 C -0.1450(4) 0.0426(7) 0.1902(4) 0.0236(13) Uani 1 1 d . . .
C8 C -0.1087(4) 0.0205(8) 0.2891(3) 0.0318(15) Uani 1 1 d . . .
H8A H -0.1317 -0.0830 0.3071 0.048 Uiso 1 1 calc R . .
H8B H -0.1294 0.1118 0.3199 0.048 Uiso 1 1 calc R . .
H8C H -0.0415 0.0183 0.3043 0.048 Uiso 1 1 calc R . .
C9 C -0.2493(4) 0.0478(7) 0.1632(4) 0.0314(15) Uani 1 1 d . . .
H9A H -0.2704 0.0726 0.0999 0.047 Uiso 1 1 calc R . .
H9B H -0.2710 0.1329 0.1973 0.047 Uiso 1 1 calc R . .
H9C H -0.2737 -0.0589 0.1751 0.047 Uiso 1 1 calc R . .
C10 C 0.1935(4) 0.0755(7) 0.1793(4) 0.0220(14) Uani 1 1 d . . .
C11 C 0.2197(4) 0.0937(7) 0.0995(4) 0.0265(14) Uani 1 1 d . . .
C12 C 0.3184(4) 0.1154(7) 0.0979(4) 0.0251(14) Uani 1 1 d . . .
C13 C 0.3390(4) 0.2134(7) 0.0328(4) 0.0298(16) Uani 1 1 d . . .
H13 H 0.2916 0.2726 -0.0069 0.036 Uiso 1 1 calc R . .
C14 C 0.4284(4) 0.2249(8) 0.0256(4) 0.0362(17) Uani 1 1 d . . .
H14 H 0.4423 0.2932 -0.0186 0.043 Uiso 1 1 calc R . .
C15 C 0.4969(4) 0.1386(8) 0.0817(4) 0.0362(17) Uani 1 1 d . . .
H15 H 0.5582 0.1460 0.0763 0.043 Uiso 1 1 calc R . .
C16 C 0.4770(4) 0.0413(8) 0.1460(4) 0.0352(16) Uani 1 1 d . . .
H16 H 0.5246 -0.0186 0.1851 0.042 Uiso 1 1 calc R . .
C17 C 0.3893(4) 0.0299(8) 0.1540(4) 0.0299(15) Uani 1 1 d . . .
H17 H 0.3765 -0.0379 0.1989 0.036 Uiso 1 1 calc R . .
C18 C 0.2425(4) 0.1224(7) 0.2679(4) 0.0238(14) Uani 1 1 d . . .
C19 C 0.2311(4) 0.1399(8) 0.4164(4) 0.0334(16) Uani 1 1 d . . .
H19A H 0.2650 0.2451 0.4226 0.040 Uiso 1 1 calc R . .
H19B H 0.2746 0.0514 0.4426 0.040 Uiso 1 1 calc R . .
C20 C 0.1539(4) 0.1491(8) 0.4614(4) 0.0392(18) Uani 1 1 d . . .
H20A H 0.1178 0.2486 0.4423 0.059 Uiso 1 1 calc R . .
H20B H 0.1793 0.1522 0.5258 0.059 Uiso 1 1 calc R . .
H20C H 0.1144 0.0527 0.4455 0.059 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 C10 2.068(5) . ?
I1 C1 2.132(6) . ?
O1 C7 1.431(6) . ?
O1 H1 0.8400 . ?
O2 C11 1.254(6) . ?
O3 C18 1.210(6) . ?
O4 C18 1.351(6) . ?
O4 C19 1.433(6) . ?
C1 C6 1.381(7) . ?
C1 C2 1.394(8) . ?
C2 C3 1.371(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.411(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.544(8) . ?
C7 C8 1.510(7) . ?
C7 C9 1.520(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.406(8) . ?
C10 C18 1.445(7) . ?
C11 C12 1.503(7) . ?
C12 C17 1.385(7) . ?
C12 C13 1.389(7) . ?
C13 C14 1.382(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.371(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.360(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 C20 1.506(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C10 I1 C1 98.7(2) . . ?
C7 O1 H1 109.5 . . ?
C18 O4 C19 116.7(4) . . ?
C6 C1 C2 122.3(5) . . ?
C6 C1 I1 120.3(4) . . ?
C2 C1 I1 117.4(4) . . ?
C3 C2 C1 119.1(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.6(6) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.8(6) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 122.0(6) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 116.2(5) . . ?
C1 C6 C7 123.1(5) . . ?
C5 C6 C7 120.7(5) . . ?
O1 C7 C8 106.2(4) . . ?
O1 C7 C9 108.5(5) . . ?
C8 C7 C9 111.5(5) . . ?
O1 C7 C6 107.9(4) . . ?
C8 C7 C6 109.2(5) . . ?
C9 C7 C6 113.3(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C18 129.1(5) . . ?
C11 C10 I1 113.2(4) . . ?
C18 C10 I1 117.6(4) . . ?
O2 C11 C10 121.9(5) . . ?
O2 C11 C12 116.2(5) . . ?
C10 C11 C12 121.8(5) . . ?
C17 C12 C13 118.1(5) . . ?
C17 C12 C11 122.5(5) . . ?
C13 C12 C11 119.1(5) . . ?
C14 C13 C12 120.2(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.3(6) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.8(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.3(6) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 121.2(6) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
O3 C18 O4 122.0(5) . . ?
O3 C18 C10 126.9(5) . . ?
O4 C18 C10 111.1(5) . . ?
O4 C19 C20 105.9(5) . . ?
O4 C19 H19A 110.6 . . ?
C20 C19 H19A 110.6 . . ?
O4 C19 H19B 110.6 . . ?
C20 C19 H19B 110.6 . . ?
H19A C19 H19B 108.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 I1 C1 C6 -157.3(5) . . . . ?
C10 I1 C1 C2 20.4(5) . . . . ?
C6 C1 C2 C3 1.2(9) . . . . ?
I1 C1 C2 C3 -176.5(4) . . . . ?
C1 C2 C3 C4 -0.4(9) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
C3 C4 C5 C6 -0.7(9) . . . . ?
C2 C1 C6 C5 -1.6(8) . . . . ?
I1 C1 C6 C5 176.0(4) . . . . ?
C2 C1 C6 C7 -179.2(5) . . . . ?
I1 C1 C6 C7 -1.5(7) . . . . ?
C4 C5 C6 C1 1.4(8) . . . . ?
C4 C5 C6 C7 179.0(5) . . . . ?
C1 C6 C7 O1 -32.5(7) . . . . ?
C5 C6 C7 O1 150.0(5) . . . . ?
C1 C6 C7 C8 82.4(7) . . . . ?
C5 C6 C7 C8 -95.0(6) . . . . ?
C1 C6 C7 C9 -152.6(5) . . . . ?
C5 C6 C7 C9 29.9(7) . . . . ?
C1 I1 C10 C11 -90.4(4) . . . . ?
C1 I1 C10 C18 87.7(4) . . . . ?
C18 C10 C11 O2 -161.5(6) . . . . ?
I1 C10 C11 O2 16.3(7) . . . . ?
C18 C10 C11 C12 21.3(9) . . . . ?
I1 C10 C11 C12 -160.8(4) . . . . ?
O2 C11 C12 C17 -137.7(6) . . . . ?
C10 C11 C12 C17 39.6(9) . . . . ?
O2 C11 C12 C13 36.3(8) . . . . ?
C10 C11 C12 C13 -146.3(6) . . . . ?
C17 C12 C13 C14 -0.5(9) . . . . ?
C11 C12 C13 C14 -174.9(5) . . . . ?
C12 C13 C14 C15 0.8(9) . . . . ?
C13 C14 C15 C16 -0.6(10) . . . . ?
C14 C15 C16 C17 0.1(10) . . . . ?
C15 C16 C17 C12 0.1(10) . . . . ?
C13 C12 C17 C16 0.1(9) . . . . ?
C11 C12 C17 C16 174.2(6) . . . . ?
C19 O4 C18 O3 -5.1(8) . . . . ?
C19 O4 C18 C10 176.5(5) . . . . ?
C11 C10 C18 O3 -7.4(10) . . . . ?
I1 C10 C18 O3 174.8(5) . . . . ?
C11 C10 C18 O4 171.0(6) . . . . ?
I1 C10 C18 O4 -6.8(6) . . . . ?
C18 O4 C19 C20 168.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.82 2.654(5) 173.5 3

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.737
_refine_diff_density_min         -1.008
_refine_diff_density_rms         0.155

