# Electronic Supplementary Material (ESI) for ChemComm.
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1486638'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-benzyl-2-phenyl-4-(trifluoromethyl)-2,5-dihydro-1H-pyrrole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 F3 N'
_chemical_formula_weight         303.32

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.2485(12)
_cell_length_b                   9.5833(19)
_cell_length_c                   26.376(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1579.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1705
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      18.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_T_max  0.9882
_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 Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18515
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2794
_reflns_number_gt                1467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0405P)²+0.0704P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.0(13)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2794
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1255(4) 0.2027(3) 0.07156(9) 0.1198(9) Uani 1 1 d . . .
F2 F 0.3298(4) 0.3523(2) 0.10452(8) 0.1127(8) Uani 1 1 d . . .
F3 F 0.3972(4) 0.2754(2) 0.03102(8) 0.1079(8) Uani 1 1 d . . .
N1 N 0.5339(4) -0.0605(2) 0.15066(9) 0.0551(7) Uani 1 1 d . . .
C1 C 0.3943(8) -0.0724(4) 0.27994(16) 0.0954(12) Uani 1 1 d . . .
H1A H 0.4983 -0.0086 0.2899 0.114 Uiso 1 1 calc R . .
C2 C 0.2193(10) -0.0989(6) 0.31147(18) 0.1204(17) Uani 1 1 d . . .
H2A H 0.2036 -0.0508 0.3419 0.144 Uiso 1 1 calc R . .
C3 C 0.0737(9) -0.1948(7) 0.2973(2) 0.1232(18) Uani 1 1 d . . .
H3A H -0.0409 -0.2142 0.3186 0.148 Uiso 1 1 calc R . .
C4 C 0.0901(8) -0.2632(5) 0.2529(2) 0.1091(15) Uani 1 1 d . . .
H4A H -0.0132 -0.3281 0.2435 0.131 Uiso 1 1 calc R . .
C5 C 0.2612(7) -0.2362(4) 0.22144(15) 0.0816(11) Uani 1 1 d . . .
H5A H 0.2736 -0.2840 0.1909 0.098 Uiso 1 1 calc R . .
C6 C 0.4132(6) -0.1398(4) 0.23458(13) 0.0665(9) Uani 1 1 d . . .
C7 C 0.6019(5) -0.1104(3) 0.20060(12) 0.0715(10) Uani 1 1 d . . .
H7A H 0.6925 -0.0405 0.2164 0.086 Uiso 1 1 calc R . .
H7B H 0.6857 -0.1949 0.1966 0.086 Uiso 1 1 calc R . .
C8 C 0.4144(5) 0.0702(3) 0.15133(11) 0.0606(9) Uani 1 1 d . . .
H8A H 0.4671 0.1329 0.1774 0.073 Uiso 1 1 calc R . .
H8B H 0.2626 0.0542 0.1564 0.073 Uiso 1 1 calc R . .
C9 C 0.4595(5) 0.1251(3) 0.09927(12) 0.0580(8) Uani 1 1 d . . .
C10 C 0.6255(5) 0.0622(3) 0.07921(12) 0.0621(8) Uani 1 1 d . . .
H10A H 0.6820 0.0826 0.0475 0.075 Uiso 1 1 calc R . .
C11 C 0.7112(5) -0.0463(3) 0.11419(11) 0.0570(8) Uani 1 1 d . . .
H11A H 0.8372 -0.0093 0.1318 0.068 Uiso 1 1 calc R . .
C12 C 0.7672(5) -0.1841(3) 0.09039(11) 0.0597(8) Uani 1 1 d . . .
C13 C 0.6189(7) -0.2561(4) 0.06304(13) 0.0797(10) Uani 1 1 d . . .
H13A H 0.4832 -0.2182 0.0585 0.096 Uiso 1 1 calc R . .
C14 C 0.6661(8) -0.3850(4) 0.04180(15) 0.0940(12) Uani 1 1 d . . .
H14A H 0.5632 -0.4334 0.0234 0.113 Uiso 1 1 calc R . .
C15 C 0.8662(9) -0.4396(4) 0.04836(15) 0.0949(13) Uani 1 1 d . . .
H15A H 0.8991 -0.5268 0.0350 0.114 Uiso 1 1 calc R . .
C16 C 1.0179(7) -0.3668(5) 0.07451(16) 0.0970(13) Uani 1 1 d . . .
H16A H 1.1545 -0.4037 0.0784 0.116 Uiso 1 1 calc R . .
C17 C 0.9691(5) -0.2391(3) 0.09502(13) 0.0745(10) Uani 1 1 d . . .
H17A H 1.0740 -0.1893 0.1123 0.089 Uiso 1 1 calc R . .
C18 C 0.3304(7) 0.2363(4) 0.07664(15) 0.0797(11) 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
F1 C18 1.327(4) . ?
F2 C18 1.333(4) . ?
F3 C18 1.328(4) . ?
N1 C8 1.458(3) . ?
N1 C7 1.464(3) . ?
N1 C11 1.474(3) . ?
C1 C6 1.365(5) . ?
C1 C2 1.397(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.346(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.346(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.370(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.508(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.497(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.311(4) . ?
C9 C18 1.464(4) . ?
C10 C11 1.490(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.503(4) . ?
C11 H11A 0.9800 . ?
C12 C13 1.363(4) . ?
C12 C17 1.373(4) . ?
C13 C14 1.387(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.367(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.364(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.372(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?

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 C7 114.7(2) . . ?
C8 N1 C11 108.3(2) . . ?
C7 N1 C11 113.5(2) . . ?
C6 C1 C2 120.3(4) . . ?
C6 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?
C3 C2 C1 119.2(5) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C4 C3 C2 121.5(5) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C1 C6 C5 118.7(4) . . ?
C1 C6 C7 120.0(4) . . ?
C5 C6 C7 121.2(3) . . ?
N1 C7 C6 111.6(3) . . ?
N1 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C9 101.2(2) . . ?
N1 C8 H8A 111.5 . . ?
C9 C8 H8A 111.5 . . ?
N1 C8 H8B 111.5 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
C10 C9 C18 127.3(3) . . ?
C10 C9 C8 110.9(3) . . ?
C18 C9 C8 121.8(3) . . ?
C9 C10 C11 110.8(3) . . ?
C9 C10 H10A 124.6 . . ?
C11 C10 H10A 124.6 . . ?
N1 C11 C10 101.4(2) . . ?
N1 C11 C12 111.5(2) . . ?
C10 C11 C12 116.0(3) . . ?
N1 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C13 C12 C17 118.5(3) . . ?
C13 C12 C11 120.5(3) . . ?
C17 C12 C11 120.9(3) . . ?
C12 C13 C14 121.3(4) . . ?
C12 C13 H13A 119.3 . . ?
C14 C13 H13A 119.3 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14A 120.5 . . ?
C13 C14 H14A 120.5 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C16 C17 C12 120.8(4) . . ?
C16 C17 H17A 119.6 . . ?
C12 C17 H17A 119.6 . . ?
F1 C18 F3 106.3(3) . . ?
F1 C18 F2 104.8(3) . . ?
F3 C18 F2 105.4(3) . . ?
F1 C18 C9 113.3(3) . . ?
F3 C18 C9 113.7(3) . . ?
F2 C18 C9 112.6(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 2.1(6) . . . . ?
C1 C2 C3 C4 -1.6(7) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C2 C1 C6 C5 -1.8(5) . . . . ?
C2 C1 C6 C7 179.7(3) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C8 N1 C7 C6 61.7(4) . . . . ?
C11 N1 C7 C6 -173.1(3) . . . . ?
C1 C6 C7 N1 -121.8(3) . . . . ?
C5 C6 C7 N1 59.8(4) . . . . ?
C7 N1 C8 C9 154.4(3) . . . . ?
C11 N1 C8 C9 26.5(3) . . . . ?
N1 C8 C9 C10 -17.4(3) . . . . ?
N1 C8 C9 C18 163.6(3) . . . . ?
C18 C9 C10 C11 -179.4(3) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C8 N1 C11 C10 -25.7(3) . . . . ?
C7 N1 C11 C10 -154.3(2) . . . . ?
C8 N1 C11 C12 -149.8(3) . . . . ?
C7 N1 C11 C12 81.6(3) . . . . ?
C9 C10 C11 N1 14.7(3) . . . . ?
C9 C10 C11 C12 135.6(3) . . . . ?
N1 C11 C12 C13 60.2(4) . . . . ?
C10 C11 C12 C13 -55.2(4) . . . . ?
N1 C11 C12 C17 -120.8(3) . . . . ?
C10 C11 C12 C17 123.8(3) . . . . ?
C17 C12 C13 C14 2.5(5) . . . . ?
C11 C12 C13 C14 -178.5(3) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
C14 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 C12 1.2(6) . . . . ?
C13 C12 C17 C16 -2.9(5) . . . . ?
C11 C12 C17 C16 178.1(3) . . . . ?
C10 C9 C18 F1 120.5(4) . . . . ?
C8 C9 C18 F1 -60.7(4) . . . . ?
C10 C9 C18 F3 -1.0(5) . . . . ?
C8 C9 C18 F3 177.9(3) . . . . ?
C10 C9 C18 F2 -120.8(4) . . . . ?
C8 C9 C18 F2 58.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.030
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DCM
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1498966'
_audit_update_record             
;
2016-08-12 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-benzyl-3-iodo-2-phenyl-4-(trifluoromethyl)-1H-pyrrole
_chemical_name_common            ?
_chemical_melting_point          335.9-337.6
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 F3 I N'
_chemical_formula_weight         427.19

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'

_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                   11.015(4)
_cell_length_b                   14.627(5)
_cell_length_c                   11.621(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.793(9)
_cell_angle_gamma                90.00
_cell_volume                     1726.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9745
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    1.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4591
_exptl_absorpt_correction_T_max  0.6609
_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 Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18868
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3027
_reflns_number_gt                2634
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0224P)²+2.0734P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3027
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0736
_refine_ls_wR_factor_gt          0.0687
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
I1 I 0.11170(3) 0.14365(2) 0.57878(2) 0.07450(12) Uani 1 1 d . . .
F1 F 0.3308(3) 0.0061(3) 0.4942(3) 0.1333(13) Uani 1 1 d . . .
F2 F 0.3927(3) 0.1410(2) 0.4873(4) 0.1504(16) Uani 1 1 d . . .
F3 F 0.3795(2) 0.0484(2) 0.3464(3) 0.1033(9) Uani 1 1 d . . .
N1 N -0.0016(3) 0.13430(18) 0.1881(2) 0.0502(6) Uani 1 1 d . . .
C1 C -0.1208(4) -0.0438(3) 0.1064(3) 0.0670(10) Uani 1 1 d . . .
H1A H -0.0328 -0.0435 0.1610 0.080 Uiso 1 1 calc R . .
C2 C -0.1923(6) -0.1237(3) 0.0866(4) 0.0885(14) Uani 1 1 d . . .
H2A H -0.1521 -0.1767 0.1281 0.106 Uiso 1 1 calc R . .
C3 C -0.3200(6) -0.1258(4) 0.0074(5) 0.0986(16) Uani 1 1 d . . .
H3A H -0.3674 -0.1801 -0.0060 0.118 Uiso 1 1 calc R . .
C4 C -0.3798(5) -0.0473(4) -0.0532(5) 0.1035(16) Uani 1 1 d . . .
H4A H -0.4678 -0.0483 -0.1075 0.124 Uiso 1 1 calc R . .
C5 C -0.3088(4) 0.0334(3) -0.0334(4) 0.0802(11) Uani 1 1 d . . .
H5A H -0.3496 0.0865 -0.0743 0.096 Uiso 1 1 calc R . .
C6 C -0.1783(3) 0.0358(2) 0.0463(3) 0.0548(8) Uani 1 1 d . . .
C7 C -0.1560(3) 0.1848(2) 0.2847(3) 0.0467(7) Uani 1 1 d . . .
C8 C -0.2293(3) 0.1387(2) 0.3391(4) 0.0608(9) Uani 1 1 d . . .
H8A H -0.1973 0.0846 0.3824 0.073 Uiso 1 1 calc R . .
C9 C -0.3497(4) 0.1724(3) 0.3296(4) 0.0786(12) Uani 1 1 d . . .
H9A H -0.3979 0.1413 0.3675 0.094 Uiso 1 1 calc R . .
C10 C -0.3988(4) 0.2510(3) 0.2648(4) 0.0814(12) Uani 1 1 d . . .
H10A H -0.4810 0.2726 0.2571 0.098 Uiso 1 1 calc R . .
C11 C -0.3277(4) 0.2975(3) 0.2118(4) 0.0769(11) Uani 1 1 d . . .
H11A H -0.3611 0.3512 0.1682 0.092 Uiso 1 1 calc R . .
C12 C -0.2063(3) 0.2660(2) 0.2218(3) 0.0608(9) Uani 1 1 d . . .
H12A H -0.1575 0.2991 0.1864 0.073 Uiso 1 1 calc R . .
C13 C -0.0276(3) 0.14962(19) 0.2933(3) 0.0432(6) Uani 1 1 d . . .
C14 C 0.0847(3) 0.1306(2) 0.3928(3) 0.0464(7) Uani 1 1 d . . .
C15 C 0.1823(3) 0.1029(2) 0.3484(3) 0.0499(7) Uani 1 1 d . . .
C16 C 0.1241(3) 0.1053(2) 0.2217(3) 0.0564(8) Uani 1 1 d . . .
H16A H 0.1641 0.0896 0.1671 0.068 Uiso 1 1 calc R . .
C17 C -0.1013(4) 0.1237(2) 0.0618(3) 0.0594(8) Uani 1 1 d . . .
H17A H -0.0587 0.1244 0.0028 0.071 Uiso 1 1 calc R . .
H17B H -0.1616 0.1750 0.0429 0.071 Uiso 1 1 calc R . .
C18 C 0.3192(4) 0.0759(3) 0.4197(4) 0.0674(10) 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
I1 C14 2.073(3) . ?
F1 C18 1.313(5) . ?
F2 C18 1.299(5) . ?
F3 C18 1.329(4) . ?
N1 C16 1.354(4) . ?
N1 C13 1.377(4) . ?
N1 C17 1.461(4) . ?
C1 C2 1.378(6) . ?
C1 C6 1.378(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.351(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.374(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5A 0.9300 . ?
C6 C17 1.512(5) . ?
C7 C8 1.379(4) . ?
C7 C12 1.391(4) . ?
C7 C13 1.472(4) . ?
C8 C9 1.379(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.367(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.352(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.377(5) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.356(4) . ?
C14 C15 1.420(4) . ?
C15 C16 1.360(5) . ?
C15 C18 1.465(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C16 N1 C13 109.7(3) . . ?
C16 N1 C17 122.9(3) . . ?
C13 N1 C17 125.1(3) . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C3 C2 C1 120.7(5) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 119.7(5) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 C1 118.4(4) . . ?
C5 C6 C17 119.5(3) . . ?
C1 C6 C17 122.1(3) . . ?
C8 C7 C12 118.3(3) . . ?
C8 C7 C13 121.0(3) . . ?
C12 C7 C13 120.7(3) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12A 119.8 . . ?
C7 C12 H12A 119.8 . . ?
C14 C13 N1 106.8(3) . . ?
C14 C13 C7 131.7(3) . . ?
N1 C13 C7 121.4(3) . . ?
C13 C14 C15 108.5(3) . . ?
C13 C14 I1 125.8(2) . . ?
C15 C14 I1 125.6(2) . . ?
C16 C15 C14 106.3(3) . . ?
C16 C15 C18 124.7(3) . . ?
C14 C15 C18 129.0(3) . . ?
N1 C16 C15 108.7(3) . . ?
N1 C16 H16A 125.7 . . ?
C15 C16 H16A 125.7 . . ?
N1 C17 C6 112.3(3) . . ?
N1 C17 H17A 109.1 . . ?
C6 C17 H17A 109.1 . . ?
N1 C17 H17B 109.1 . . ?
C6 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
F2 C18 F1 107.0(4) . . ?
F2 C18 F3 105.0(3) . . ?
F1 C18 F3 104.0(3) . . ?
F2 C18 C15 114.1(3) . . ?
F1 C18 C15 113.5(3) . . ?
F3 C18 C15 112.3(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 0.2(6) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 C6 0.3(8) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C4 C5 C6 C17 177.3(4) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C2 C1 C6 C17 -177.5(3) . . . . ?
C12 C7 C8 C9 0.7(5) . . . . ?
C13 C7 C8 C9 -179.7(3) . . . . ?
C7 C8 C9 C10 0.9(6) . . . . ?
C8 C9 C10 C11 -1.5(7) . . . . ?
C9 C10 C11 C12 0.4(7) . . . . ?
C10 C11 C12 C7 1.3(6) . . . . ?
C8 C7 C12 C11 -1.8(5) . . . . ?
C13 C7 C12 C11 178.6(3) . . . . ?
C16 N1 C13 C14 0.7(3) . . . . ?
C17 N1 C13 C14 163.6(3) . . . . ?
C16 N1 C13 C7 177.8(3) . . . . ?
C17 N1 C13 C7 -19.3(4) . . . . ?
C8 C7 C13 C14 -58.7(5) . . . . ?
C12 C7 C13 C14 120.9(4) . . . . ?
C8 C7 C13 N1 124.9(3) . . . . ?
C12 C7 C13 N1 -55.5(4) . . . . ?
N1 C13 C14 C15 0.0(3) . . . . ?
C7 C13 C14 C15 -176.7(3) . . . . ?
N1 C13 C14 I1 178.2(2) . . . . ?
C7 C13 C14 I1 1.4(5) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
I1 C14 C15 C16 -178.8(2) . . . . ?
C13 C14 C15 C18 179.7(3) . . . . ?
I1 C14 C15 C18 1.5(5) . . . . ?
C13 N1 C16 C15 -1.1(4) . . . . ?
C17 N1 C16 C15 -164.5(3) . . . . ?
C14 C15 C16 N1 1.1(4) . . . . ?
C18 C15 C16 N1 -179.2(3) . . . . ?
C16 N1 C17 C6 91.9(4) . . . . ?
C13 N1 C17 C6 -68.9(4) . . . . ?
C5 C6 C17 N1 146.9(3) . . . . ?
C1 C6 C17 N1 -35.4(4) . . . . ?
C16 C15 C18 F2 115.7(4) . . . . ?
C14 C15 C18 F2 -64.7(5) . . . . ?
C16 C15 C18 F1 -121.3(4) . . . . ?
C14 C15 C18 F1 58.3(5) . . . . ?
C16 C15 C18 F3 -3.7(5) . . . . ?
C14 C15 C18 F3 175.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.057
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/petroleum'
