# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_lsh_4_0m
_database_code_depnum_ccdc_archive 'CCDC 1541589'
_audit_update_record             
;
2017-04-01 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H29 F I2 N4 O'
_chemical_formula_weight         650.30

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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.840(3)
_cell_length_b                   12.067(5)
_cell_length_c                   14.220(6)
_cell_angle_alpha                87.101(6)
_cell_angle_beta                 77.634(6)
_cell_angle_gamma                89.744(7)
_cell_volume                     1312.3(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2923
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.54

_exptl_crystal_description       Block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    2.424
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4842
_exptl_absorpt_correction_T_max  0.7435
_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         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7193
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5085
_reflns_number_gt                4084
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0376P)²+1.1931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5085
_refine_ls_number_parameters     290
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
F1 F 0.4296(4) 0.7804(2) -0.0101(2) 0.0752(8) Uani 1 1 d . . .
I1 I 0.17685(4) 0.23885(3) 0.85354(2) 0.05997(11) Uani 1 1 d . . .
I2 I 0.57545(4) 0.28239(3) 0.30489(2) 0.06855(12) Uani 1 1 d . . .
N1 N 0.1392(4) 0.3988(2) 0.1791(2) 0.0421(7) Uani 1 1 d . . .
N2 N 0.1005(4) 0.3432(3) 0.3449(2) 0.0441(7) Uani 1 1 d . . .
N3 N 0.2829(4) 0.5446(3) 0.3567(2) 0.0422(7) Uani 1 1 d . . .
N4 N 0.0870(4) 0.0930(2) 0.1552(2) 0.0429(7) Uani 1 1 d . . .
C1 C 0.2163(5) 0.4882(3) 0.1206(3) 0.0395(8) Uani 1 1 d . . .
C2 C 0.2316(5) 0.5061(3) 0.0212(3) 0.0473(9) Uani 1 1 d . . .
H2 H 0.1923 0.4534 -0.0150 0.057 Uiso 1 1 calc R . .
C3 C 0.3071(5) 0.6046(4) -0.0215(3) 0.0517(10) Uani 1 1 d . . .
H3 H 0.3198 0.6195 -0.0875 0.062 Uiso 1 1 calc R . .
C4 C 0.3638(5) 0.6813(3) 0.0350(3) 0.0528(10) Uani 1 1 d . . .
C5 C 0.3600(5) 0.6646(3) 0.1311(3) 0.0467(9) Uani 1 1 d . . .
H5 H 0.4052 0.7169 0.1651 0.056 Uiso 1 1 calc R . .
C6 C 0.2848(5) 0.5649(3) 0.1762(3) 0.0386(8) Uani 1 1 d . . .
C7 C 0.2503(5) 0.5156(3) 0.2722(3) 0.0378(8) Uani 1 1 d . . .
C8 C 0.1576(5) 0.4125(3) 0.2710(3) 0.0391(8) Uani 1 1 d . . .
C9 C 0.1355(5) 0.3743(3) 0.4294(3) 0.0455(9) Uani 1 1 d . . .
C10 C 0.0798(6) 0.3027(4) 0.5124(3) 0.0575(11) Uani 1 1 d . . .
H10 H 0.0230 0.2365 0.5073 0.069 Uiso 1 1 calc R . .
C11 C 0.1088(6) 0.3300(5) 0.6000(3) 0.0661(13) Uani 1 1 d . . .
H11 H 0.0723 0.2821 0.6539 0.079 Uiso 1 1 calc R . .
C12 C 0.1932(6) 0.4296(5) 0.6087(3) 0.0654(13) Uani 1 1 d . . .
H12 H 0.2100 0.4475 0.6690 0.079 Uiso 1 1 calc R . .
C13 C 0.2522(6) 0.5020(4) 0.5304(3) 0.0567(11) Uani 1 1 d . . .
H13 H 0.3086 0.5677 0.5376 0.068 Uiso 1 1 calc R . .
C14 C 0.2256(5) 0.4749(3) 0.4389(3) 0.0454(9) Uani 1 1 d . . .
C15 C 0.0513(5) 0.3023(3) 0.1523(3) 0.0446(9) Uani 1 1 d . . .
H15A H 0.0115 0.3201 0.0933 0.053 Uiso 1 1 calc R . .
H15B H -0.0497 0.2822 0.2027 0.053 Uiso 1 1 calc R . .
C16 C 0.1774(5) 0.2057(3) 0.1377(3) 0.0420(8) Uani 1 1 d . . .
H16A H 0.2568 0.2108 0.1811 0.050 Uiso 1 1 calc R . .
H16B H 0.2464 0.2115 0.0723 0.050 Uiso 1 1 calc R . .
C17 C 0.0188(6) 0.0628(4) 0.2617(3) 0.0572(11) Uani 1 1 d . . .
H17A H -0.0525 -0.0039 0.2683 0.069 Uiso 1 1 calc R . .
H17B H -0.0550 0.1222 0.2906 0.069 Uiso 1 1 calc R . .
C18 C 0.1652(8) 0.0433(4) 0.3157(4) 0.0766(15) Uani 1 1 d . . .
H18A H 0.1154 0.0177 0.3816 0.092 Uiso 1 1 calc R . .
H18B H 0.2256 0.1129 0.3175 0.092 Uiso 1 1 calc R . .
C19 C 0.2960(8) -0.0421(5) 0.2686(5) 0.0916(19) Uani 1 1 d . . .
H19A H 0.3919 -0.0476 0.3018 0.110 Uiso 1 1 calc R . .
H19B H 0.2396 -0.1142 0.2742 0.110 Uiso 1 1 calc R . .
C20 C 0.3664(7) -0.0089(4) 0.1626(4) 0.0747(15) Uani 1 1 d . . .
H20A H 0.4320 0.0599 0.1571 0.090 Uiso 1 1 calc R . .
H20B H 0.4447 -0.0658 0.1329 0.090 Uiso 1 1 calc R . .
C21 C 0.2170(6) 0.0060(3) 0.1101(3) 0.0588(11) Uani 1 1 d . . .
H21A H 0.1567 -0.0644 0.1119 0.071 Uiso 1 1 calc R . .
H21B H 0.2641 0.0283 0.0431 0.071 Uiso 1 1 calc R . .
C22 C -0.0659(6) 0.0932(4) 0.1062(3) 0.0531(10) Uani 1 1 d . . .
H22A H -0.1561 0.1400 0.1392 0.080 Uiso 1 1 calc R . .
H22B H -0.1103 0.0189 0.1077 0.080 Uiso 1 1 calc R . .
H22C H -0.0285 0.1206 0.0404 0.080 Uiso 1 1 calc R . .
C23 C 0.3816(6) 0.6475(4) 0.3599(3) 0.0587(11) Uani 1 1 d . . .
H23A H 0.3044 0.7098 0.3631 0.088 Uiso 1 1 calc R . .
H23B H 0.4727 0.6561 0.3030 0.088 Uiso 1 1 calc R . .
H23C H 0.4320 0.6435 0.4158 0.088 Uiso 1 1 calc R . .
O1 O 0.655(2) 0.067(3) 0.4813(15) 0.76(3) Uani 1 1 d D . .
H1A H 0.743(3) 0.1100(17) 0.4806(19) -0.006(5) Uiso 1 1 d D . .
H1B H 0.679(8) 0.000(5) 0.469(17) 0.40(13) Uiso 1 1 d 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
F1 C4 1.376(5) . ?
N1 C8 1.363(5) . ?
N1 C1 1.386(5) . ?
N1 C15 1.464(5) . ?
N2 C8 1.310(5) . ?
N2 C9 1.360(5) . ?
N3 C7 1.343(4) . ?
N3 C14 1.399(5) . ?
N3 C23 1.473(5) . ?
N4 C22 1.510(5) . ?
N4 C17 1.520(5) . ?
N4 C16 1.521(5) . ?
N4 C21 1.526(5) . ?
C1 C2 1.399(5) . ?
C1 C6 1.424(5) . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(6) . ?
C5 C6 1.405(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.433(5) . ?
C7 C8 1.446(5) . ?
C9 C10 1.418(6) . ?
C9 C14 1.434(6) . ?
C10 C11 1.369(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.415(5) . ?
C13 H13 0.9300 . ?
C15 C16 1.518(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.523(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.525(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.524(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.523(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O1 H1A 0.865(10) . ?
O1 H1B 0.849(10) . ?

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
C8 N1 C1 108.9(3) . . ?
C8 N1 C15 122.7(3) . . ?
C1 N1 C15 128.4(3) . . ?
C8 N2 C9 114.5(3) . . ?
C7 N3 C14 119.0(3) . . ?
C7 N3 C23 119.3(3) . . ?
C14 N3 C23 121.7(3) . . ?
C22 N4 C17 108.0(3) . . ?
C22 N4 C16 109.6(3) . . ?
C17 N4 C16 112.6(3) . . ?
C22 N4 C21 108.3(3) . . ?
C17 N4 C21 110.1(3) . . ?
C16 N4 C21 108.2(3) . . ?
N1 C1 C2 127.9(3) . . ?
N1 C1 C6 110.2(3) . . ?
C2 C1 C6 121.9(3) . . ?
C3 C2 C1 117.7(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 F1 118.2(4) . . ?
C5 C4 C3 124.6(4) . . ?
F1 C4 C3 117.1(4) . . ?
C4 C5 C6 117.0(4) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 135.7(3) . . ?
C1 C6 C7 105.2(3) . . ?
N3 C7 C6 134.8(3) . . ?
N3 C7 C8 117.9(3) . . ?
C6 C7 C8 107.4(3) . . ?
N2 C8 N1 125.2(3) . . ?
N2 C8 C7 126.5(3) . . ?
N1 C8 C7 108.3(3) . . ?
N2 C9 C10 117.8(4) . . ?
N2 C9 C14 123.7(3) . . ?
C10 C9 C14 118.5(4) . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 121.8(4) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119.0(5) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
N3 C14 C13 121.8(4) . . ?
N3 C14 C9 118.5(3) . . ?
C13 C14 C9 119.8(4) . . ?
N1 C15 C16 109.4(3) . . ?
N1 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
N1 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 N4 113.3(3) . . ?
C15 C16 H16A 108.9 . . ?
N4 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
N4 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
N4 C17 C18 112.5(4) . . ?
N4 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
N4 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 112.0(4) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C18 110.6(4) . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 110.4(5) . . ?
C21 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 N4 111.8(4) . . ?
C20 C21 H21A 109.2 . . ?
N4 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
N4 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H1A O1 H1B 116(2) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.247
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.073
