# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_yoshi95m
_database_code_depnum_ccdc_archive 'CCDC 1981452'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT906_yoshi95m            
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.003 Check
RESPONSE: Checked. It is not caused by an omission or oversight
;
_vrf_PLAT911_yoshi95m            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
RESPONSE: Checked. It is not caused by an omission or oversight
;
_vrf_PLAT934_yoshi95m            
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check
RESPONSE: Checked. It is not caused by an omission or oversight
;
# Added during the CSD deposition process: Monday 03 February 2020 02:03 AM
# end Validation Reply Form

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 F6 I N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         517.16

_chemical_melting_point          271-273

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5364(3)
_cell_length_b                   8.1598(3)
_cell_length_c                   14.6308(6)
_cell_angle_alpha                74.8246(15)
_cell_angle_beta                 86.9207(15)
_cell_angle_gamma                83.5890(14)
_cell_volume                     862.64(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7468
_cell_measurement_theta_min      2.5997
_cell_measurement_theta_max      31.4720
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500

_exptl_absorpt_coefficient_mu    1.938
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.83

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            20823
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         33.80
_diffrn_reflns_theta_full        33.80
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_reflns_number_total             6892
_reflns_number_gt                5554
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0791
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         6892
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0148P)²+0.7450P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.770
_refine_diff_density_min         -1.134
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5841(4) 0.3201(3) 0.23384(18) 0.0160(5) Uani d . . . 1 . .
C C2 0.4802(3) 0.4691(3) 0.23941(18) 0.0166(5) Uani d . . . 1 . .
H H2 0.400367 0.470823 0.291741 0.02 Uiso calc U . R 1 . .
C C3 0.4960(4) 0.6151(3) 0.16662(19) 0.0187(5) Uani d . . . 1 . .
H H3 0.427705 0.719134 0.168942 0.022 Uiso calc U . R 1 . .
C C4 0.6119(4) 0.6088(4) 0.09028(19) 0.0203(5) Uani d . . . 1 . .
H H4 0.621256 0.708555 0.040023 0.024 Uiso calc U . R 1 . .
C C5 0.7145(4) 0.4580(4) 0.08663(19) 0.0192(5) Uani d . . . 1 . .
H H5 0.793483 0.455783 0.034026 0.023 Uiso calc U . R 1 . .
C C6 0.7026(4) 0.3097(3) 0.15957(18) 0.0162(5) Uani d . . . 1 . .
C C7 0.8108(4) 0.1369(3) 0.16156(18) 0.0167(5) Uani d . . . 1 . .
C C8 0.7583(4) 0.0735(4) 0.0774(2) 0.0225(6) Uani d . . . 1 . .
C C9 1.0122(4) 0.1589(4) 0.15599(19) 0.0210(6) Uani d . . . 1 . .
C C10 0.3793(4) 0.2079(3) 0.42896(18) 0.0158(5) Uani d . . . 1 . .
C C11 0.1977(3) 0.1838(3) 0.43380(18) 0.0159(5) Uani d . . . 1 . .
H H11 0.146078 0.132579 0.391699 0.019 Uiso calc U . R 1 . .
C C12 0.0989(3) 0.2396(3) 0.50396(18) 0.0144(5) Uani d . . . 1 . .
C C13 0.1734(3) 0.3122(3) 0.56713(17) 0.0124(4) Uani d . . . 1 . .
C C14 0.3519(3) 0.3369(3) 0.56214(18) 0.0155(5) Uani d . . . 1 . .
H H14 0.402095 0.388941 0.604347 0.019 Uiso calc U . R 1 . .
C C15 0.4552(3) 0.2815(3) 0.49175(18) 0.0160(5) Uani d . . . 1 . .
H H15 0.57941 0.29404 0.486446 0.019 Uiso calc U . R 1 . .
C C16 -0.1167(4) 0.2876(3) 0.60748(19) 0.0176(5) Uani d . . . 1 . .
C C17 0.0545(4) 0.3994(4) 0.71469(19) 0.0207(6) Uani d . . . 1 . .
H H17A -0.062233 0.407915 0.746921 0.031 Uiso calc U . R 1 . .
H H17B 0.100914 0.511295 0.697649 0.031 Uiso calc U . R 1 . .
H H17C 0.137589 0.31654 0.756999 0.031 Uiso calc U . R 1 . .
F F1 0.5838(2) 0.0510(2) 0.08540(14) 0.0347(4) Uani d . . . 1 . .
F F2 0.8472(3) -0.0766(2) 0.07548(12) 0.0282(4) Uani d . . . 1 . .
F F3 0.7840(3) 0.1803(2) -0.00754(12) 0.0280(4) Uani d . . . 1 . .
F F4 1.1133(2) 0.0105(2) 0.16745(13) 0.0308(4) Uani d . . . 1 . .
F F5 1.0676(2) 0.2620(2) 0.07499(12) 0.0283(4) Uani d . . . 1 . .
F F6 1.0529(3) 0.2264(3) 0.22571(13) 0.0346(5) Uani d . . . 1 . .
I I1 0.56286(2) 0.09166(2) 0.34153(2) 0.01746(5) Uani d . . . 1 . .
N N1 0.0357(3) 0.3437(3) 0.62921(15) 0.0150(4) Uani d . . . 1 . .
O O1 0.7790(3) 0.0157(3) 0.24262(14) 0.0267(5) Uani d . . . 1 . .
O O2 -0.0795(2) 0.2257(3) 0.52724(13) 0.0186(4) Uani d . . . 1 . .
O O3 -0.2617(3) 0.2882(3) 0.64531(15) 0.0240(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.383(4) ?
C1 C2 . 1.389(4) ?
C1 I1 . 2.118(3) ?
C2 C3 . 1.386(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.389(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.390(4) ?
C4 H4 . 0.95 ?
C5 C6 . 1.396(4) ?
C5 H5 . 0.95 ?
C6 C7 . 1.542(4) ?
C7 O1 . 1.360(3) ?
C7 C8 . 1.541(4) ?
C7 C9 . 1.543(4) ?
C8 F2 . 1.334(3) ?
C8 F3 . 1.336(3) ?
C8 F1 . 1.343(3) ?
C9 F4 . 1.333(3) ?
C9 F5 . 1.338(3) ?
C9 F6 . 1.343(3) ?
C10 C15 . 1.398(4) ?
C10 C11 . 1.400(4) ?
C10 I1 . 2.145(2) ?
C11 C12 . 1.379(3) ?
C11 H11 . 0.95 ?
C12 O2 . 1.379(3) ?
C12 C13 . 1.392(3) ?
C13 C14 . 1.378(3) ?
C13 N1 . 1.389(3) ?
C14 C15 . 1.396(4) ?
C14 H14 . 0.95 ?
C15 H15 . 0.95 ?
C16 O3 . 1.198(3) ?
C16 N1 . 1.364(3) ?
C16 O2 . 1.399(3) ?
C17 N1 . 1.457(3) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
I1 O1 . 2.2633(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 123.5(2) ?
C6 C1 I1 . . 116.38(19) ?
C2 C1 I1 . . 120.12(19) ?
C3 C2 C1 . . 118.3(2) ?
C3 C2 H2 . . 120.9 ?
C1 C2 H2 . . 120.9 ?
C2 C3 C4 . . 119.8(2) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C4 C5 C6 . . 120.6(2) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C1 C6 C5 . . 117.1(2) ?
C1 C6 C7 . . 118.6(2) ?
C5 C6 C7 . . 124.2(2) ?
O1 C7 C6 . . 112.0(2) ?
O1 C7 C8 . . 108.0(2) ?
C6 C7 C8 . . 109.2(2) ?
O1 C7 C9 . . 107.7(2) ?
C6 C7 C9 . . 109.4(2) ?
C8 C7 C9 . . 110.6(2) ?
F2 C8 F3 . . 106.9(2) ?
F2 C8 F1 . . 107.0(2) ?
F3 C8 F1 . . 106.7(2) ?
F2 C8 C7 . . 112.1(2) ?
F3 C8 C7 . . 114.5(2) ?
F1 C8 C7 . . 109.2(2) ?
F4 C9 F5 . . 106.8(2) ?
F4 C9 F6 . . 106.6(2) ?
F5 C9 F6 . . 106.4(2) ?
F4 C9 C7 . . 112.2(2) ?
F5 C9 C7 . . 114.6(2) ?
F6 C9 C7 . . 109.7(2) ?
C15 C10 C11 . . 122.2(2) ?
C15 C10 I1 . . 116.15(19) ?
C11 C10 I1 . . 120.74(18) ?
C12 C11 C10 . . 115.3(2) ?
C12 C11 H11 . . 122.3 ?
C10 C11 H11 . . 122.3 ?
O2 C12 C11 . . 127.7(2) ?
O2 C12 C13 . . 109.3(2) ?
C11 C12 C13 . . 122.9(2) ?
C14 C13 N1 . . 132.1(2) ?
C14 C13 C12 . . 121.8(2) ?
N1 C13 C12 . . 106.1(2) ?
C13 C14 C15 . . 116.5(2) ?
C13 C14 H14 . . 121.8 ?
C15 C14 H14 . . 121.8 ?
C14 C15 C10 . . 121.3(2) ?
C14 C15 H15 . . 119.4 ?
C10 C15 H15 . . 119.4 ?
O3 C16 N1 . . 129.9(2) ?
O3 C16 O2 . . 122.2(2) ?
N1 C16 O2 . . 107.8(2) ?
N1 C17 H17A . . 109.5 ?
N1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C1 I1 C10 . . 94.78(10) ?
C1 I1 O1 . . 76.58(8) ?
C10 I1 O1 . . 169.35(9) ?
C16 N1 C13 . . 109.6(2) ?
C16 N1 C17 . . 123.7(2) ?
C13 N1 C17 . . 125.9(2) ?
C7 O1 I1 . . 116.07(15) ?
C12 O2 C16 . . 107.09(19) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and hexane'
