# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1451801'
_audit_update_record             
;
2016-02-04 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 F3 I N0 O2'
_chemical_formula_weight         416.12

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3920(11)
_cell_length_b                   15.7128(16)
_cell_length_c                   9.0091(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.556(3)
_cell_angle_gamma                90.00
_cell_volume                     1435.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7064
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    2.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5693
_exptl_absorpt_correction_T_max  0.6354
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9177
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2512
_reflns_number_gt                2169
_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)+(0.0555P)²+2.2678P] 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         2512
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C1 C 0.2741(4) 0.0320(3) 0.4653(5) 0.0390(10) Uani 1 1 d . . .
H1 H 0.3467 0.0501 0.5381 0.047 Uiso 1 1 calc R . .
C2 C 0.2070(5) -0.0407(3) 0.4887(5) 0.0506(13) Uani 1 1 d . . .
H2 H 0.2349 -0.0720 0.5776 0.061 Uiso 1 1 calc R . .
C3 C 0.0994(4) -0.0674(2) 0.3818(5) 0.0377(10) Uani 1 1 d . . .
H3 H 0.0539 -0.1162 0.3989 0.045 Uiso 1 1 calc R . .
C4 C 0.0593(4) -0.0224(2) 0.2505(5) 0.0314(9) Uani 1 1 d . . .
H4 H -0.0136 -0.0406 0.1782 0.038 Uiso 1 1 calc R . .
C5 C 0.1259(4) 0.0497(2) 0.2245(4) 0.0280(8) Uani 1 1 d . . .
H5 H 0.0992 0.0795 0.1338 0.034 Uiso 1 1 calc R . .
C6 C 0.2324(3) 0.07784(19) 0.3326(4) 0.0175(7) Uani 1 1 d . . .
C7 C 0.2991(3) 0.1591(2) 0.3055(4) 0.0161(7) Uani 1 1 d . . .
C8 C 0.2526(4) 0.2357(2) 0.3356(4) 0.0186(7) Uani 1 1 d . . .
C9 C 0.3148(3) 0.3161(2) 0.3064(4) 0.0200(7) Uani 1 1 d . . .
C10 C 0.4675(4) 0.2328(2) 0.2001(4) 0.0173(7) Uani 1 1 d . . .
C11 C 0.5715(4) 0.2354(2) 0.1285(5) 0.0216(8) Uani 1 1 d . . .
H11 H 0.6057 0.2871 0.1048 0.026 Uiso 1 1 calc R . .
C12 C 0.6238(3) 0.1593(2) 0.0927(4) 0.0222(7) Uani 1 1 d . . .
C13 C 0.5758(3) 0.0816(2) 0.1307(4) 0.0228(7) Uani 1 1 d . . .
H13 H 0.6143 0.0310 0.1088 0.027 Uiso 1 1 calc R . .
C14 C 0.4710(3) 0.0801(2) 0.2011(4) 0.0210(7) Uani 1 1 d . . .
H14 H 0.4375 0.0282 0.2246 0.025 Uiso 1 1 calc R . .
C15 C 0.4137(3) 0.1561(2) 0.2379(4) 0.0166(7) Uani 1 1 d . . .
C16 C 0.7368(4) 0.1589(2) 0.0130(5) 0.0298(8) Uani 1 1 d . . .
F1 F 0.7046(3) 0.11989(18) -0.1213(3) 0.0506(7) Uani 1 1 d . . .
F2 F 0.8400(3) 0.1192(2) 0.0912(4) 0.0718(10) Uani 1 1 d . . .
F3 F 0.7745(4) 0.23637(18) -0.0188(5) 0.0622(10) Uani 1 1 d . . .
I1 I 0.08333(2) 0.250204(11) 0.41932(3) 0.02245(15) Uani 1 1 d . . .
O1 O 0.2836(3) 0.38618(15) 0.3374(3) 0.0293(6) Uani 1 1 d . . .
O2 O 0.4182(2) 0.30983(14) 0.2353(3) 0.0206(5) 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 C2 1.379(6) . ?
C1 C6 1.382(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.498(4) . ?
C7 C8 1.347(5) . ?
C7 C15 1.452(5) . ?
C8 C9 1.469(5) . ?
C8 I1 2.072(4) . ?
C9 O1 1.198(4) . ?
C9 O2 1.369(4) . ?
C10 C11 1.375(6) . ?
C10 O2 1.378(4) . ?
C10 C15 1.401(5) . ?
C11 C12 1.380(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(5) . ?
C12 C16 1.504(5) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.405(5) . ?
C14 H14 0.9300 . ?
C16 F2 1.307(5) . ?
C16 F3 1.328(5) . ?
C16 F1 1.333(5) . ?

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
C2 C1 C6 119.4(4) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 C7 119.1(3) . . ?
C1 C6 C7 121.1(3) . . ?
C8 C7 C15 118.4(3) . . ?
C8 C7 C6 122.0(3) . . ?
C15 C7 C6 119.5(3) . . ?
C7 C8 C9 122.8(4) . . ?
C7 C8 I1 122.8(3) . . ?
C9 C8 I1 114.3(2) . . ?
O1 C9 O2 117.1(3) . . ?
O1 C9 C8 126.6(3) . . ?
O2 C9 C8 116.2(3) . . ?
C11 C10 O2 116.8(3) . . ?
C11 C10 C15 122.4(3) . . ?
O2 C10 C15 120.8(3) . . ?
C10 C11 C12 118.3(3) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C11 C12 C13 121.5(3) . . ?
C11 C12 C16 120.2(3) . . ?
C13 C12 C16 118.2(3) . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 117.5(3) . . ?
C10 C15 C7 118.8(3) . . ?
C14 C15 C7 123.7(3) . . ?
F2 C16 F3 107.9(4) . . ?
F2 C16 F1 106.5(3) . . ?
F3 C16 F1 104.7(3) . . ?
F2 C16 C12 112.3(3) . . ?
F3 C16 C12 113.4(3) . . ?
F1 C16 C12 111.5(3) . . ?
C9 O2 C10 122.7(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
C6 C1 C2 C3 -0.3(8) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 -1.3(6) . . . . ?
C4 C5 C6 C1 1.8(6) . . . . ?
C4 C5 C6 C7 -176.8(3) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
C2 C1 C6 C7 177.5(4) . . . . ?
C5 C6 C7 C8 82.5(5) . . . . ?
C1 C6 C7 C8 -96.1(5) . . . . ?
C5 C6 C7 C15 -94.5(4) . . . . ?
C1 C6 C7 C15 86.9(4) . . . . ?
C15 C7 C8 C9 -1.5(6) . . . . ?
C6 C7 C8 C9 -178.5(3) . . . . ?
C15 C7 C8 I1 176.1(2) . . . . ?
C6 C7 C8 I1 -0.9(5) . . . . ?
C7 C8 C9 O1 -175.8(4) . . . . ?
I1 C8 C9 O1 6.4(5) . . . . ?
C7 C8 C9 O2 4.9(5) . . . . ?
I1 C8 C9 O2 -173.0(2) . . . . ?
O2 C10 C11 C12 179.5(3) . . . . ?
C15 C10 C11 C12 0.2(6) . . . . ?
C10 C11 C12 C13 -1.6(6) . . . . ?
C10 C11 C12 C16 179.4(3) . . . . ?
C11 C12 C13 C14 2.2(5) . . . . ?
C16 C12 C13 C14 -178.8(3) . . . . ?
C12 C13 C14 C15 -1.4(5) . . . . ?
C11 C10 C15 C14 0.6(5) . . . . ?
O2 C10 C15 C14 -178.8(3) . . . . ?
C11 C10 C15 C7 -176.5(3) . . . . ?
O2 C10 C15 C7 4.2(5) . . . . ?
C13 C14 C15 C10 0.0(5) . . . . ?
C13 C14 C15 C7 176.9(3) . . . . ?
C8 C7 C15 C10 -3.0(5) . . . . ?
C6 C7 C15 C10 174.1(3) . . . . ?
C8 C7 C15 C14 -179.9(3) . . . . ?
C6 C7 C15 C14 -2.8(5) . . . . ?
C11 C12 C16 F2 121.4(4) . . . . ?
C13 C12 C16 F2 -57.7(5) . . . . ?
C11 C12 C16 F3 -1.3(5) . . . . ?
C13 C12 C16 F3 179.6(4) . . . . ?
C11 C12 C16 F1 -119.2(4) . . . . ?
C13 C12 C16 F1 61.8(4) . . . . ?
O1 C9 O2 C10 176.9(3) . . . . ?
C8 C9 O2 C10 -3.7(5) . . . . ?
C11 C10 O2 C9 179.9(3) . . . . ?
C15 C10 O2 C9 -0.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.709
_refine_diff_density_min         -1.573
_refine_diff_density_rms         0.154
