# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a51228a
_database_code_depnum_ccdc_archive 'CCDC 1477485'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 F3 I N O'
_chemical_formula_weight         471.24

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   31.800(14)
_cell_length_b                   8.994(4)
_cell_length_c                   13.605(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.595(5)
_cell_angle_gamma                90
_cell_volume                     3643(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    822
_cell_measurement_theta_min      2.988
_cell_measurement_theta_max      25.624

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.796
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.284
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7945
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.366
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3564
_reflns_number_gt                2648
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0489P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3564
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.02154(2) 0.32260(3) 0.43239(2) 0.06528(12) Uani 1 1 d . . . . .
F1 F 0.22399(8) 0.1360(2) 0.81258(16) 0.0702(6) Uani 1 1 d . . . . .
F2 F 0.15750(7) 0.0889(3) 0.71121(19) 0.0904(8) Uani 1 1 d . . . . .
F3 F 0.21263(9) -0.0258(2) 0.69354(18) 0.0854(7) Uani 1 1 d . . . . .
N1 N 0.17575(8) 0.4936(3) 0.4911(2) 0.0448(6) Uani 1 1 d . . . . .
O1 O 0.20648(8) 0.3255(3) 0.41427(18) 0.0575(6) Uani 1 1 d . . . . .
C1 C 0.18555(10) 0.3520(3) 0.4716(2) 0.0417(7) Uani 1 1 d . . . . .
C2 C 0.16953(9) 0.2252(3) 0.5266(2) 0.0346(6) Uani 1 1 d . . . . .
C3 C 0.12219(9) 0.2727(3) 0.5198(2) 0.0332(6) Uani 1 1 d . . . . .
C4 C 0.12478(9) 0.4152(3) 0.5757(2) 0.0360(7) Uani 1 1 d . . . . .
C5 C 0.10408(10) 0.4401(3) 0.6482(2) 0.0449(7) Uani 1 1 d . . . . .
H5 H 0.0863 0.3660 0.6610 0.054 Uiso 1 1 calc R U . . .
C6 C 0.10941(12) 0.5729(4) 0.7015(3) 0.0565(9) Uani 1 1 d . . . . .
H6 H 0.0950 0.5887 0.7494 0.068 Uiso 1 1 calc R U . . .
C7 C 0.13610(13) 0.6816(4) 0.6837(3) 0.0583(10) Uani 1 1 d . . . . .
H7 H 0.1394 0.7719 0.7189 0.070 Uiso 1 1 calc R U . . .
C8 C 0.15782(12) 0.6580(3) 0.6144(3) 0.0528(9) Uani 1 1 d . . . . .
H8 H 0.1760 0.7321 0.6033 0.063 Uiso 1 1 calc R U . . .
C9 C 0.15288(10) 0.5245(3) 0.5606(2) 0.0401(7) Uani 1 1 d . . . . .
C10 C 0.20358(9) 0.2261(3) 0.6416(2) 0.0378(7) Uani 1 1 d . . . . .
H10A H 0.2336 0.2197 0.6390 0.045 Uiso 1 1 calc R U . . .
H10B H 0.2012 0.3215 0.6725 0.045 Uiso 1 1 calc R U . . .
C11 C 0.19904(11) 0.1074(4) 0.7140(3) 0.0491(8) Uani 1 1 d . . . . .
C12 C 0.08367(9) 0.2080(3) 0.4620(2) 0.0377(7) Uani 1 1 d . . . . .
C13 C 0.07458(9) 0.0607(3) 0.4099(2) 0.0371(7) Uani 1 1 d . . . . .
C14 C 0.06404(10) 0.0470(3) 0.3019(3) 0.0467(8) Uani 1 1 d . . . . .
H14 H 0.0630 0.1309 0.2612 0.056 Uiso 1 1 calc R U . . .
C15 C 0.05512(11) -0.0918(4) 0.2555(3) 0.0587(9) Uani 1 1 d . . . . .
H15 H 0.0484 -0.1009 0.1835 0.070 Uiso 1 1 calc R U . . .
C16 C 0.05602(12) -0.2164(4) 0.3147(3) 0.0577(9) Uani 1 1 d . . . . .
H16 H 0.0505 -0.3096 0.2831 0.069 Uiso 1 1 calc R U . . .
C17 C 0.06509(11) -0.2025(3) 0.4200(3) 0.0547(9) Uani 1 1 d . . . . .
H17 H 0.0649 -0.2862 0.4599 0.066 Uiso 1 1 calc R U . . .
C18 C 0.07453(10) -0.0650(3) 0.4674(3) 0.0484(8) Uani 1 1 d . . . . .
H18 H 0.0810 -0.0571 0.5394 0.058 Uiso 1 1 calc R U . . .
C19 C 0.17387(10) 0.0786(3) 0.4737(3) 0.0464(8) Uani 1 1 d . . . . .
H19A H 0.1632 -0.0016 0.5051 0.070 Uiso 1 1 calc R U . . .
H19B H 0.2048 0.0618 0.4828 0.070 Uiso 1 1 calc R U . . .
H19C H 0.1564 0.0837 0.4002 0.070 Uiso 1 1 calc R U . . .
C20 C 0.19105(13) 0.6165(4) 0.4413(3) 0.0666(10) Uani 1 1 d . . . . .
H20A H 0.2171 0.6617 0.4917 0.100 Uiso 1 1 calc R U . . .
H20B H 0.1676 0.6892 0.4164 0.100 Uiso 1 1 calc R U . . .
H20C H 0.1985 0.5793 0.3834 0.100 Uiso 1 1 calc R U . . .


_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 C12 2.138(3) . ?
F1 C11 1.321(4) . ?
F2 C11 1.319(4) . ?
F3 C11 1.336(4) . ?
N1 C1 1.359(4) . ?
N1 C9 1.409(4) . ?
N1 C20 1.466(4) . ?
O1 C1 1.214(4) . ?
C1 C2 1.545(4) . ?
C2 C19 1.531(4) . ?
C2 C3 1.536(4) . ?
C2 C10 1.559(4) . ?
C3 C12 1.334(4) . ?
C3 C4 1.478(4) . ?
C4 C5 1.383(4) . ?
C4 C9 1.391(4) . ?
C5 C6 1.377(4) . ?
C6 C7 1.371(5) . ?
C7 C8 1.367(5) . ?
C8 C9 1.386(4) . ?
C10 C11 1.493(4) . ?
C12 C13 1.481(4) . ?
C13 C18 1.375(4) . ?
C13 C14 1.393(4) . ?
C14 C15 1.383(5) . ?
C15 C16 1.374(5) . ?
C16 C17 1.364(5) . ?
C17 C18 1.378(4) . ?

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
C1 N1 C9 121.6(2) . . ?
C1 N1 C20 118.8(3) . . ?
C9 N1 C20 119.6(3) . . ?
O1 C1 N1 121.6(3) . . ?
O1 C1 C2 121.0(3) . . ?
N1 C1 C2 117.4(3) . . ?
C19 C2 C3 117.4(2) . . ?
C19 C2 C1 108.0(2) . . ?
C3 C2 C1 104.4(2) . . ?
C19 C2 C10 109.3(2) . . ?
C3 C2 C10 112.3(2) . . ?
C1 C2 C10 104.6(2) . . ?
C12 C3 C4 123.7(3) . . ?
C12 C3 C2 126.2(3) . . ?
C4 C3 C2 109.5(2) . . ?
C5 C4 C9 118.9(3) . . ?
C5 C4 C3 123.5(3) . . ?
C9 C4 C3 117.4(2) . . ?
C6 C5 C4 121.0(3) . . ?
C7 C6 C5 119.6(3) . . ?
C8 C7 C6 120.4(3) . . ?
C7 C8 C9 120.5(3) . . ?
C8 C9 C4 119.6(3) . . ?
C8 C9 N1 122.4(3) . . ?
C4 C9 N1 118.0(3) . . ?
C11 C10 C2 117.7(2) . . ?
F2 C11 F1 106.9(3) . . ?
F2 C11 F3 106.0(3) . . ?
F1 C11 F3 105.3(3) . . ?
F2 C11 C10 113.5(3) . . ?
F1 C11 C10 111.6(3) . . ?
F3 C11 C10 113.0(3) . . ?
C3 C12 C13 131.0(3) . . ?
C3 C12 I1 119.8(2) . . ?
C13 C12 I1 109.21(18) . . ?
C18 C13 C14 118.6(3) . . ?
C18 C13 C12 120.2(3) . . ?
C14 C13 C12 121.2(3) . . ?
C15 C14 C13 119.8(3) . . ?
C16 C15 C14 120.7(3) . . ?
C17 C16 C15 119.6(3) . . ?
C16 C17 C18 120.3(3) . . ?
C13 C18 C17 121.0(3) . . ?

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
C9 N1 C1 O1 -177.7(3) . . . . ?
C20 N1 C1 O1 -0.1(5) . . . . ?
C9 N1 C1 C2 1.6(4) . . . . ?
C20 N1 C1 C2 179.1(3) . . . . ?
O1 C1 C2 C19 -14.3(4) . . . . ?
N1 C1 C2 C19 166.5(3) . . . . ?
O1 C1 C2 C3 -139.9(3) . . . . ?
N1 C1 C2 C3 40.9(3) . . . . ?
O1 C1 C2 C10 102.0(3) . . . . ?
N1 C1 C2 C10 -77.2(3) . . . . ?
C19 C2 C3 C12 -8.5(4) . . . . ?
C1 C2 C3 C12 111.0(3) . . . . ?
C10 C2 C3 C12 -136.4(3) . . . . ?
C19 C2 C3 C4 179.6(3) . . . . ?
C1 C2 C3 C4 -61.0(3) . . . . ?
C10 C2 C3 C4 51.7(3) . . . . ?
C12 C3 C4 C5 56.4(4) . . . . ?
C2 C3 C4 C5 -131.4(3) . . . . ?
C12 C3 C4 C9 -129.5(3) . . . . ?
C2 C3 C4 C9 42.7(3) . . . . ?
C9 C4 C5 C6 2.8(5) . . . . ?
C3 C4 C5 C6 176.9(3) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C4 1.5(5) . . . . ?
C7 C8 C9 N1 -177.9(3) . . . . ?
C5 C4 C9 C8 -3.1(4) . . . . ?
C3 C4 C9 C8 -177.5(3) . . . . ?
C5 C4 C9 N1 176.3(3) . . . . ?
C3 C4 C9 N1 1.9(4) . . . . ?
C1 N1 C9 C8 153.3(3) . . . . ?
C20 N1 C9 C8 -24.2(4) . . . . ?
C1 N1 C9 C4 -26.0(4) . . . . ?
C20 N1 C9 C4 156.4(3) . . . . ?
C19 C2 C10 C11 -60.3(3) . . . . ?
C3 C2 C10 C11 71.7(3) . . . . ?
C1 C2 C10 C11 -175.7(3) . . . . ?
C2 C10 C11 F2 -47.4(4) . . . . ?
C2 C10 C11 F1 -168.3(2) . . . . ?
C2 C10 C11 F3 73.3(4) . . . . ?
C4 C3 C12 C13 -173.2(3) . . . . ?
C2 C3 C12 C13 16.0(5) . . . . ?
C4 C3 C12 I1 6.8(4) . . . . ?
C2 C3 C12 I1 -164.1(2) . . . . ?
C3 C12 C13 C18 79.2(4) . . . . ?
I1 C12 C13 C18 -100.8(3) . . . . ?
C3 C12 C13 C14 -103.6(4) . . . . ?
I1 C12 C13 C14 76.4(3) . . . . ?
C18 C13 C14 C15 -1.9(4) . . . . ?
C12 C13 C14 C15 -179.1(3) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C14 C15 C16 C17 1.1(5) . . . . ?
C15 C16 C17 C18 -1.8(5) . . . . ?
C14 C13 C18 C17 1.2(4) . . . . ?
C12 C13 C18 C17 178.4(3) . . . . ?
C16 C17 C18 C13 0.7(5) . . . . ?

_refine_diff_density_max         0.874
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-2



