# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1856642'
_audit_update_record             
;
2018-07-18 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H15 F3 I3 P'
_chemical_formula_weight         772.03

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.1640(9)
_cell_length_b                   10.9788(11)
_cell_length_c                   13.5101(13)
_cell_angle_alpha                87.9470(10)
_cell_angle_beta                 72.5210(10)
_cell_angle_gamma                76.2900(10)
_cell_volume                     1258.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9249
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.83
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    3.820
_shelx_estimated_absorpt_T_min   0.272
_shelx_estimated_absorpt_T_max   0.531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5814
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21984
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.581
_diffrn_reflns_theta_max         28.201
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5727
_reflns_number_gt                4763
_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       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0185P)²+2.0298P] 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         5727
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0607
_refine_ls_wR_factor_gt          0.0568
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_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
C1 C 1.0309(4) 0.6039(3) 0.6007(3) 0.0379(7) Uani 1 1 d . . . . .
C2 C 0.9347(4) 0.5384(3) 0.6678(3) 0.0383(7) Uani 1 1 d . . . . .
C3 C 0.7794(4) 0.5515(3) 0.6729(2) 0.0383(7) Uani 1 1 d . . . . .
C4 C 0.7208(3) 0.6371(3) 0.6086(2) 0.0361(7) Uani 1 1 d . . . . .
C5 C 0.8101(4) 0.7056(3) 0.5394(2) 0.0349(7) Uani 1 1 d . . . . .
C6 C 0.9660(4) 0.6858(3) 0.5372(2) 0.0369(7) Uani 1 1 d . . . . .
C7 C 0.6165(4) -0.0130(3) 0.7498(2) 0.0395(7) Uani 1 1 d . . . . .
C8 C 0.7236(5) 0.0408(4) 0.6766(3) 0.0565(10) Uani 1 1 d . . . . .
H8 H 0.686787 0.105541 0.635198 0.068 Uiso 1 1 calc R U . . .
C9 C 0.8833(5) 0.0006(4) 0.6639(4) 0.0664(12) Uani 1 1 d . . . . .
H9 H 0.955581 0.038562 0.614551 0.080 Uiso 1 1 calc R U . . .
C10 C 0.9380(5) -0.0946(4) 0.7226(3) 0.0587(10) Uani 1 1 d . . . . .
H10 H 1.047509 -0.120940 0.714680 0.070 Uiso 1 1 calc R U . . .
C11 C 0.8343(4) -0.1509(4) 0.7921(3) 0.0523(9) Uani 1 1 d . . . . .
H11 H 0.872596 -0.217938 0.831057 0.063 Uiso 1 1 calc R U . . .
C12 C 0.6736(4) -0.1110(3) 0.8065(3) 0.0437(8) Uani 1 1 d . . . . .
H12 H 0.602587 -0.150671 0.855107 0.052 Uiso 1 1 calc R U . . .
C13 C 0.3107(4) -0.0544(3) 0.8554(3) 0.0390(7) Uani 1 1 d . . . . .
C14 C 0.3049(5) -0.1668(4) 0.8146(3) 0.0547(10) Uani 1 1 d . . . . .
H14 H 0.349785 -0.185805 0.742182 0.066 Uiso 1 1 calc R U . . .
C15 C 0.2339(5) -0.2520(4) 0.8788(4) 0.0665(12) Uani 1 1 d . . . . .
H15 H 0.233818 -0.329827 0.850279 0.080 Uiso 1 1 calc R U . . .
C16 C 0.1642(5) -0.2239(4) 0.9828(4) 0.0598(11) Uani 1 1 d . . . . .
H16 H 0.114367 -0.281496 1.026146 0.072 Uiso 1 1 calc R U . . .
C17 C 0.1666(5) -0.1118(4) 1.0243(3) 0.0557(10) Uani 1 1 d . . . . .
H17 H 0.117969 -0.092095 1.096426 0.067 Uiso 1 1 calc R U . . .
C18 C 0.2400(4) -0.0274(3) 0.9610(3) 0.0461(8) Uani 1 1 d . . . . .
H18 H 0.241740 0.049427 0.990363 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3646(4) 0.1917(3) 0.8473(2) 0.0363(7) Uani 1 1 d . . . . .
C20 C 0.2322(4) 0.2870(3) 0.8475(3) 0.0451(8) Uani 1 1 d . . . . .
H20 H 0.171068 0.278438 0.803617 0.054 Uiso 1 1 calc R U . . .
C21 C 0.1901(5) 0.3933(4) 0.9110(3) 0.0528(9) Uani 1 1 d . . . . .
H21 H 0.099825 0.457163 0.910762 0.063 Uiso 1 1 calc R U . . .
C22 C 0.2777(5) 0.4076(3) 0.9747(3) 0.0494(9) Uani 1 1 d . . . . .
H22 H 0.247150 0.480301 1.019110 0.059 Uiso 1 1 calc R U . . .
C23 C 0.4108(4) 0.3151(3) 0.9736(3) 0.0455(8) Uani 1 1 d . . . . .
H23 H 0.472865 0.325223 1.016439 0.055 Uiso 1 1 calc R U . . .
C24 C 0.4534(4) 0.2085(3) 0.9105(3) 0.0413(7) Uani 1 1 d . . . . .
H24 H 0.544824 0.145728 0.910375 0.050 Uiso 1 1 calc R U . . .
F1 F 0.9935(3) 0.4582(2) 0.73190(18) 0.0608(6) Uani 1 1 d . . . . .
F2 F 0.5686(2) 0.6532(2) 0.61314(16) 0.0521(5) Uani 1 1 d . . . . .
F3 F 1.0584(2) 0.7496(2) 0.47013(17) 0.0569(6) Uani 1 1 d . . . . .
I1 I 1.26322(3) 0.58399(3) 0.59864(2) 0.06064(9) Uani 1 1 d . . . . .
I2 I 0.63808(4) 0.44657(3) 0.77245(2) 0.06420(9) Uani 1 1 d . . . . .
I3 I 0.71668(3) 0.82544(2) 0.43700(2) 0.04970(7) Uani 1 1 d . . . . .
P1 P 0.40732(11) 0.05112(8) 0.76442(7) 0.03954(19) 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 1.374(5) . ?
C1 C6 1.378(5) . ?
C1 I1 2.080(3) . ?
C2 F1 1.348(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.381(5) . ?
C3 I2 2.089(3) . ?
C4 F2 1.347(3) . ?
C4 C5 1.375(4) . ?
C5 C6 1.384(4) . ?
C5 I3 2.104(3) . ?
C6 F3 1.343(4) . ?
C7 C12 1.390(5) . ?
C7 C8 1.393(5) . ?
C7 P1 1.831(3) . ?
C8 C9 1.384(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.388(5) . ?
C13 C18 1.389(5) . ?
C13 P1 1.834(4) . ?
C14 C15 1.393(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.370(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.388(5) . ?
C19 C20 1.401(4) . ?
C19 P1 1.834(3) . ?
C20 C21 1.381(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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 117.4(3) . . ?
C2 C1 I1 121.2(2) . . ?
C6 C1 I1 121.4(2) . . ?
F1 C2 C1 119.1(3) . . ?
F1 C2 C3 118.2(3) . . ?
C1 C2 C3 122.7(3) . . ?
C2 C3 C4 117.0(3) . . ?
C2 C3 I2 121.8(2) . . ?
C4 C3 I2 121.2(2) . . ?
F2 C4 C5 118.3(3) . . ?
F2 C4 C3 118.2(3) . . ?
C5 C4 C3 123.5(3) . . ?
C4 C5 C6 116.4(3) . . ?
C4 C5 I3 121.3(2) . . ?
C6 C5 I3 122.3(2) . . ?
F3 C6 C1 118.3(3) . . ?
F3 C6 C5 118.6(3) . . ?
C1 C6 C5 123.1(3) . . ?
C12 C7 C8 118.8(3) . . ?
C12 C7 P1 124.3(3) . . ?
C8 C7 P1 117.0(3) . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C14 C13 C18 118.4(3) . . ?
C14 C13 P1 117.3(3) . . ?
C18 C13 P1 124.3(3) . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.9(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.2(4) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.6(3) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C24 C19 C20 118.3(3) . . ?
C24 C19 P1 124.2(2) . . ?
C20 C19 P1 117.5(3) . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.5(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 120.9(3) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C7 P1 C19 101.41(15) . . ?
C7 P1 C13 103.16(15) . . ?
C19 P1 C13 102.04(15) . . ?

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 F1 -179.4(3) . . . . ?
I1 C1 C2 F1 -1.3(4) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
I1 C1 C2 C3 178.5(3) . . . . ?
F1 C2 C3 C4 178.1(3) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
F1 C2 C3 I2 -2.1(4) . . . . ?
C1 C2 C3 I2 178.0(2) . . . . ?
C2 C3 C4 F2 -178.9(3) . . . . ?
I2 C3 C4 F2 1.4(4) . . . . ?
C2 C3 C4 C5 1.7(5) . . . . ?
I2 C3 C4 C5 -178.0(2) . . . . ?
F2 C4 C5 C6 -179.9(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
F2 C4 C5 I3 -3.4(4) . . . . ?
C3 C4 C5 I3 175.9(2) . . . . ?
C2 C1 C6 F3 -179.2(3) . . . . ?
I1 C1 C6 F3 2.7(4) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
I1 C1 C6 C5 -177.2(2) . . . . ?
C4 C5 C6 F3 179.3(3) . . . . ?
I3 C5 C6 F3 2.9(4) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
I3 C5 C6 C1 -177.3(2) . . . . ?
C12 C7 C8 C9 -2.6(6) . . . . ?
P1 C7 C8 C9 177.6(3) . . . . ?
C7 C8 C9 C10 0.9(7) . . . . ?
C8 C9 C10 C11 1.2(7) . . . . ?
C9 C10 C11 C12 -1.8(6) . . . . ?
C10 C11 C12 C7 0.1(6) . . . . ?
C8 C7 C12 C11 2.1(5) . . . . ?
P1 C7 C12 C11 -178.1(3) . . . . ?
C18 C13 C14 C15 -1.9(6) . . . . ?
P1 C13 C14 C15 179.8(3) . . . . ?
C13 C14 C15 C16 2.1(6) . . . . ?
C14 C15 C16 C17 -1.0(7) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C14 C13 C18 C17 0.6(5) . . . . ?
P1 C13 C18 C17 178.8(3) . . . . ?
C16 C17 C18 C13 0.4(6) . . . . ?
C24 C19 C20 C21 -1.5(5) . . . . ?
P1 C19 C20 C21 177.6(3) . . . . ?
C19 C20 C21 C22 0.3(6) . . . . ?
C20 C21 C22 C23 1.0(6) . . . . ?
C21 C22 C23 C24 -1.2(5) . . . . ?
C22 C23 C24 C19 0.0(5) . . . . ?
C20 C19 C24 C23 1.3(5) . . . . ?
P1 C19 C24 C23 -177.7(3) . . . . ?
C12 C7 P1 C19 99.7(3) . . . . ?
C8 C7 P1 C19 -80.5(3) . . . . ?
C12 C7 P1 C13 -5.7(3) . . . . ?
C8 C7 P1 C13 174.1(3) . . . . ?
C24 C19 P1 C7 -21.8(3) . . . . ?
C20 C19 P1 C7 159.2(3) . . . . ?
C24 C19 P1 C13 84.5(3) . . . . ?
C20 C19 P1 C13 -94.5(3) . . . . ?
C14 C13 P1 C7 -82.2(3) . . . . ?
C18 C13 P1 C7 99.6(3) . . . . ?
C14 C13 P1 C19 172.9(3) . . . . ?
C18 C13 P1 C19 -5.3(3) . . . . ?

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
C20 H20 I3 0.95 3.26 3.937(4) 129.9 2_666
C20 H20 F1 0.95 2.60 3.263(4) 127.0 1_455
C14 H14 F2 0.95 2.57 3.365(4) 141.0 1_545
C14 H14 F2 0.95 2.57 3.365(4) 141.0 1_545
C20 H20 F1 0.95 2.60 3.263(4) 127.0 1_455
C20 H20 I3 0.95 3.26 3.937(4) 129.9 2_666

_refine_diff_density_max         1.166
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1857155'
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H15 F3 I3 O P'
_chemical_formula_weight         788.03

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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.230(2)
_cell_length_b                   10.1079(14)
_cell_length_c                   17.790(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.164(2)
_cell_angle_gamma                90
_cell_volume                     2469.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.50
_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.119
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.530
_exptl_crystal_size_min          0.440
_exptl_absorpt_coefficient_mu    3.899
_shelx_estimated_absorpt_T_min   0.127
_shelx_estimated_absorpt_T_max   0.279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5039
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29024
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.338
_diffrn_reflns_theta_max         30.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6464
_reflns_number_gt                5207
_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       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0269P)²+1.7955P] 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         6464
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0624
_refine_ls_wR_factor_gt          0.0573
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_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
C1 C 0.10997(19) 0.4086(3) 0.50315(16) 0.0330(6) Uani 1 1 d . . . . .
C2 C 0.08360(19) 0.4184(3) 0.42255(18) 0.0374(7) Uani 1 1 d . . . . .
C3 C 0.0110(2) 0.3421(3) 0.37510(17) 0.0389(7) Uani 1 1 d . . . . .
C4 C -0.0369(2) 0.2544(3) 0.41091(17) 0.0391(7) Uani 1 1 d . . . . .
C5 C -0.01696(19) 0.2417(3) 0.49069(17) 0.0351(6) Uani 1 1 d . . . . .
C6 C 0.05692(19) 0.3208(3) 0.53546(16) 0.0329(6) Uani 1 1 d . . . . .
C7 C 0.38069(18) 0.9315(3) 0.62657(16) 0.0301(6) Uani 1 1 d . . . . .
C8 C 0.3955(2) 0.9488(3) 0.55288(19) 0.0423(7) Uani 1 1 d . . . . .
H8 H 0.434651 0.887437 0.534158 0.051 Uiso 1 1 calc R U . . .
C9 C 0.3538(2) 1.0547(4) 0.50659(19) 0.0470(8) Uani 1 1 d . . . . .
H9 H 0.363892 1.065494 0.456215 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2979(2) 1.1441(3) 0.5339(2) 0.0479(8) Uani 1 1 d . . . . .
H10 H 0.269557 1.216908 0.502257 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2827(2) 1.1290(3) 0.6061(2) 0.0448(8) Uani 1 1 d . . . . .
H11 H 0.244118 1.191562 0.624526 0.054 Uiso 1 1 calc R U . . .
C12 C 0.3234(2) 1.0231(3) 0.65267(18) 0.0374(6) Uani 1 1 d . . . . .
H12 H 0.312104 1.012880 0.702675 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4213(2) 0.8085(3) 0.77906(17) 0.0337(6) Uani 1 1 d . . . . .
C14 C 0.3293(2) 0.7891(3) 0.7909(2) 0.0504(8) Uani 1 1 d . . . . .
H14 H 0.276307 0.765506 0.748266 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3147(3) 0.8041(4) 0.8644(3) 0.0623(11) Uani 1 1 d . . . . .
H15 H 0.251408 0.792512 0.871759 0.075 Uiso 1 1 calc R U . . .
C16 C 0.3916(3) 0.8357(4) 0.9268(2) 0.0633(11) Uani 1 1 d . . . . .
H16 H 0.381158 0.845851 0.977120 0.076 Uiso 1 1 calc R U . . .
C17 C 0.4830(3) 0.8526(4) 0.9167(2) 0.0562(9) Uani 1 1 d . . . . .
H17 H 0.535948 0.873687 0.959939 0.067 Uiso 1 1 calc R U . . .
C18 C 0.4981(2) 0.8389(3) 0.84303(17) 0.0417(7) Uani 1 1 d . . . . .
H18 H 0.561644 0.850505 0.836287 0.050 Uiso 1 1 calc R U . . .
C19 C 0.56241(18) 0.8005(3) 0.68539(15) 0.0290(5) Uani 1 1 d . . . . .
C20 C 0.6082(2) 0.6922(3) 0.66444(19) 0.0417(7) Uani 1 1 d . . . . .
H20 H 0.572559 0.613211 0.647979 0.050 Uiso 1 1 calc R U . . .
C21 C 0.7071(3) 0.6986(4) 0.6674(2) 0.0597(10) Uani 1 1 d . . . . .
H21 H 0.738814 0.623557 0.653166 0.072 Uiso 1 1 calc R U . . .
C22 C 0.7585(2) 0.8123(4) 0.6907(2) 0.0571(10) Uani 1 1 d . . . . .
H22 H 0.825849 0.815921 0.692891 0.069 Uiso 1 1 calc R U . . .
C23 C 0.7128(2) 0.9214(4) 0.71097(19) 0.0479(8) Uani 1 1 d . . . . .
H23 H 0.748621 1.000308 0.727098 0.057 Uiso 1 1 calc R U . . .
C24 C 0.6147(2) 0.9162(3) 0.70789(18) 0.0387(7) Uani 1 1 d . . . . .
H24 H 0.583039 0.992081 0.721204 0.046 Uiso 1 1 calc R U . . .
F1 F 0.13043(13) 0.50622(19) 0.38864(11) 0.0497(5) Uani 1 1 d . . . . .
F2 F -0.10732(13) 0.1787(2) 0.36658(11) 0.0554(5) Uani 1 1 d . . . . .
F3 F 0.07719(12) 0.31140(19) 0.61317(9) 0.0439(4) Uani 1 1 d . . . . .
I1 I 0.22725(2) 0.51936(2) 0.56943(2) 0.03531(6) Uani 1 1 d . . . . .
I2 I -0.02452(2) 0.36039(3) 0.25428(2) 0.05769(8) Uani 1 1 d . . . . .
I3 I -0.10007(2) 0.11435(2) 0.53885(2) 0.04930(7) Uani 1 1 d . . . . .
P1 P 0.43469(5) 0.78829(7) 0.68167(4) 0.02930(15) Uani 1 1 d . . . . .
O1 O 0.39205(15) 0.6605(2) 0.64553(13) 0.0432(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 C6 1.384(4) . ?
C1 C2 1.388(4) . ?
C1 I1 2.098(3) . ?
C2 F1 1.344(3) . ?
C2 C3 1.385(4) . ?
C3 C4 1.372(4) . ?
C3 I2 2.084(3) . ?
C4 F2 1.341(3) . ?
C4 C5 1.379(4) . ?
C5 C6 1.393(4) . ?
C5 I3 2.078(3) . ?
C6 F3 1.340(3) . ?
C7 C12 1.391(4) . ?
C7 C8 1.392(4) . ?
C7 P1 1.804(3) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.390(4) . ?
C13 C14 1.392(4) . ?
C13 P1 1.803(3) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.370(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.374(4) . ?
C19 C24 1.388(4) . ?
C19 P1 1.805(3) . ?
C20 C21 1.397(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.367(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
P1 O1 1.498(2) . ?

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
C6 C1 C2 116.5(3) . . ?
C6 C1 I1 123.3(2) . . ?
C2 C1 I1 120.2(2) . . ?
F1 C2 C3 118.2(3) . . ?
F1 C2 C1 118.6(3) . . ?
C3 C2 C1 123.1(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 I2 121.3(2) . . ?
C2 C3 I2 121.4(2) . . ?
F2 C4 C3 118.8(3) . . ?
F2 C4 C5 118.2(3) . . ?
C3 C4 C5 123.0(3) . . ?
C4 C5 C6 117.2(3) . . ?
C4 C5 I3 119.7(2) . . ?
C6 C5 I3 123.0(2) . . ?
F3 C6 C1 118.7(2) . . ?
F3 C6 C5 118.4(3) . . ?
C1 C6 C5 122.9(3) . . ?
C12 C7 C8 118.5(3) . . ?
C12 C7 P1 123.8(2) . . ?
C8 C7 P1 117.7(2) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C18 C13 C14 118.4(3) . . ?
C18 C13 P1 123.6(2) . . ?
C14 C13 P1 118.0(2) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.9(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C20 C19 C24 119.6(3) . . ?
C20 C19 P1 118.6(2) . . ?
C24 C19 P1 121.8(2) . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.0(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.1(3) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
O1 P1 C13 112.16(13) . . ?
O1 P1 C7 113.05(12) . . ?
C13 P1 C7 107.10(13) . . ?
O1 P1 C19 111.43(13) . . ?
C13 P1 C19 108.38(13) . . ?
C7 P1 C19 104.29(12) . . ?

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 F1 177.4(2) . . . . ?
I1 C1 C2 F1 -4.3(4) . . . . ?
C6 C1 C2 C3 -2.5(4) . . . . ?
I1 C1 C2 C3 175.8(2) . . . . ?
F1 C2 C3 C4 -179.1(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
F1 C2 C3 I2 0.6(4) . . . . ?
C1 C2 C3 I2 -179.5(2) . . . . ?
C2 C3 C4 F2 -179.8(3) . . . . ?
I2 C3 C4 F2 0.5(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
I2 C3 C4 C5 -178.4(2) . . . . ?
F2 C4 C5 C6 179.6(2) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
F2 C4 C5 I3 -2.9(4) . . . . ?
C3 C4 C5 I3 176.0(2) . . . . ?
C2 C1 C6 F3 -177.5(2) . . . . ?
I1 C1 C6 F3 4.2(4) . . . . ?
C2 C1 C6 C5 2.3(4) . . . . ?
I1 C1 C6 C5 -176.0(2) . . . . ?
C4 C5 C6 F3 179.4(2) . . . . ?
I3 C5 C6 F3 2.0(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
I3 C5 C6 C1 -177.8(2) . . . . ?
C12 C7 C8 C9 -0.2(5) . . . . ?
P1 C7 C8 C9 178.2(2) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C7 0.5(5) . . . . ?
C8 C7 C12 C11 -0.3(4) . . . . ?
P1 C7 C12 C11 -178.6(2) . . . . ?
C18 C13 C14 C15 2.0(5) . . . . ?
P1 C13 C14 C15 -179.6(3) . . . . ?
C13 C14 C15 C16 -1.3(6) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C18 0.5(6) . . . . ?
C16 C17 C18 C13 0.2(5) . . . . ?
C14 C13 C18 C17 -1.4(5) . . . . ?
P1 C13 C18 C17 -179.7(3) . . . . ?
C24 C19 C20 C21 1.3(5) . . . . ?
P1 C19 C20 C21 -179.5(3) . . . . ?
C19 C20 C21 C22 -0.3(5) . . . . ?
C20 C21 C22 C23 -0.3(6) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C19 0.9(5) . . . . ?
C20 C19 C24 C23 -1.5(4) . . . . ?
P1 C19 C24 C23 179.2(2) . . . . ?
C18 C13 P1 O1 128.1(3) . . . . ?
C14 C13 P1 O1 -50.1(3) . . . . ?
C18 C13 P1 C7 -107.3(3) . . . . ?
C14 C13 P1 C7 74.4(3) . . . . ?
C18 C13 P1 C19 4.7(3) . . . . ?
C14 C13 P1 C19 -173.6(2) . . . . ?
C12 C7 P1 O1 112.5(2) . . . . ?
C8 C7 P1 O1 -65.9(3) . . . . ?
C12 C7 P1 C13 -11.6(3) . . . . ?
C8 C7 P1 C13 170.1(2) . . . . ?
C12 C7 P1 C19 -126.3(2) . . . . ?
C8 C7 P1 C19 55.3(2) . . . . ?
C20 C19 P1 O1 -7.0(3) . . . . ?
C24 C19 P1 O1 172.3(2) . . . . ?
C20 C19 P1 C13 116.9(2) . . . . ?
C24 C19 P1 C13 -63.9(3) . . . . ?
C20 C19 P1 C7 -129.3(2) . . . . ?
C24 C19 P1 C7 50.0(3) . . . . ?

_refine_diff_density_max         0.814
_refine_diff_density_min         -1.071
_refine_diff_density_rms         0.091

