# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 1573097'
_audit_update_record             
;
2017-09-07 deposited with the CCDC.
2018-11-06 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         'C18 H10 Cl2 F N O2'
_chemical_formula_sum            'C18 H10 Cl2 F N O2'
_chemical_formula_weight         362.17

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'
Cl Cl 0.1484 0.1585 '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                   16.6493(13)
_cell_length_b                   13.1167(11)
_cell_length_c                   7.0767(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.220(9)
_cell_angle_gamma                90
_cell_volume                     1529.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1757
_cell_measurement_theta_min      3.8780
_cell_measurement_theta_max      27.5490

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.446
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 6.1049
_diffrn_reflns_number            6007
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.665
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3003
_reflns_number_gt                2041
_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       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'
_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     
'w=1/[σ²(Fo²)+(0.0725P)²+0.8139P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3003
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1822
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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
Cl1 Cl 0.24189(9) 0.12020(8) 0.24328(17) 0.0695(4) Uani 1 1 d . . . . .
Cl2 Cl 0.45066(6) 0.43851(12) 0.2835(2) 0.0777(5) Uani 1 1 d . . . . .
O2 O 0.30217(15) 0.55975(19) 0.2205(4) 0.0464(7) Uani 1 1 d . . . . .
N1 N 0.14486(17) 0.4872(2) 0.2083(4) 0.0362(7) Uani 1 1 d . . . . .
O1 O -0.03374(17) 0.7471(2) 0.0521(4) 0.0571(8) Uani 1 1 d . . . . .
C17 C 0.2108(2) 0.4188(3) 0.2264(5) 0.0363(8) Uani 1 1 d . . . . .
C16 C 0.1975(2) 0.3149(3) 0.2326(5) 0.0404(9) Uani 1 1 d . . . . .
H16 H 0.145018 0.289433 0.225577 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1349(2) 0.5696(2) 0.0886(5) 0.0341(8) Uani 1 1 d . . . . .
C2 C 0.0614(2) 0.6145(3) 0.1120(5) 0.0385(8) Uani 1 1 d . . . . .
C12 C 0.2894(2) 0.4551(3) 0.2360(5) 0.0404(9) Uani 1 1 d . . . . .
C11 C 0.2763(2) 0.5931(3) 0.0348(6) 0.0427(9) Uani 1 1 d . . . . .
C14 C 0.3427(3) 0.2825(3) 0.2660(5) 0.0494(10) Uani 1 1 d . . . . .
C7 C 0.1715(3) 0.6246(3) -0.2261(6) 0.0468(10) Uani 1 1 d . . . . .
H7 H 0.116914 0.624915 -0.277590 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0781(2) 0.4786(3) 0.3035(5) 0.0426(9) Uani 1 1 d . . . . .
H4 H 0.069974 0.428054 0.390952 0.051 Uiso 1 1 calc R U . . .
C1 C 0.0294(2) 0.7080(3) 0.0247(5) 0.0421(9) Uani 1 1 d . . . . .
H1 H 0.059478 0.740587 -0.058580 0.051 Uiso 1 1 calc R U . . .
C6 C 0.1950(2) 0.5961(3) -0.0353(5) 0.0379(8) Uani 1 1 d . . . . .
F1 F 0.41158(16) 0.6248(3) -0.0046(5) 0.0884(10) Uani 1 1 d . . . . .
C15 C 0.2629(3) 0.2498(3) 0.2494(5) 0.0466(10) Uani 1 1 d . . . . .
C3 C 0.0269(2) 0.5559(3) 0.2483(5) 0.0435(9) Uani 1 1 d . . . . .
H3 H -0.022262 0.568527 0.291711 0.052 Uiso 1 1 calc R U . . .
C13 C 0.3538(2) 0.3884(3) 0.2609(5) 0.0483(10) Uani 1 1 d . . . . .
C10 C 0.3330(3) 0.6241(3) -0.0792(7) 0.0575(12) Uani 1 1 d . . . . .
C18 C 0.4125(3) 0.2091(4) 0.2865(7) 0.0692(14) Uani 1 1 d . . . . .
H18A H 0.423349 0.185852 0.416247 0.104 Uiso 1 1 calc R U . . .
H18B H 0.459788 0.242602 0.252977 0.104 Uiso 1 1 calc R U . . .
H18C H 0.399103 0.151919 0.203321 0.104 Uiso 1 1 calc R U . . .
C8 C 0.2297(3) 0.6522(3) -0.3378(7) 0.0603(12) Uani 1 1 d . . . . .
H8 H 0.213615 0.670880 -0.464396 0.072 Uiso 1 1 calc R U . . .
C9 C 0.3099(3) 0.6526(4) -0.2657(8) 0.0673(14) Uani 1 1 d . . . . .
H9 H 0.348562 0.671910 -0.341634 0.081 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
Cl1 C15 1.734(4) . ?
Cl2 C13 1.728(4) . ?
O2 C11 1.394(5) . ?
O2 C12 1.396(5) . ?
N1 C5 1.368(4) . ?
N1 C4 1.385(4) . ?
N1 C17 1.410(4) . ?
O1 C1 1.211(4) . ?
C17 C16 1.382(5) . ?
C17 C12 1.384(5) . ?
C16 C15 1.376(5) . ?
C16 H16 0.9300 . ?
C5 C2 1.390(5) . ?
C5 C6 1.463(5) . ?
C2 C3 1.417(5) . ?
C2 C1 1.441(5) . ?
C12 C13 1.375(5) . ?
C11 C6 1.374(5) . ?
C11 C10 1.388(6) . ?
C14 C15 1.387(6) . ?
C14 C13 1.402(6) . ?
C14 C18 1.500(5) . ?
C7 C8 1.382(6) . ?
C7 C6 1.402(5) . ?
C7 H7 0.9300 . ?
C4 C3 1.345(5) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
F1 C10 1.338(5) . ?
C3 H3 0.9300 . ?
C10 C9 1.373(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C8 C9 1.361(7) . ?
C8 H8 0.9300 . ?
C9 H9 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
C11 O2 C12 110.6(3) . . ?
C5 N1 C4 109.3(3) . . ?
C5 N1 C17 125.6(3) . . ?
C4 N1 C17 125.0(3) . . ?
C16 C17 C12 119.6(3) . . ?
C16 C17 N1 120.2(3) . . ?
C12 C17 N1 120.2(3) . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
N1 C5 C2 106.9(3) . . ?
N1 C5 C6 121.8(3) . . ?
C2 C5 C6 131.3(3) . . ?
C5 C2 C3 107.5(3) . . ?
C5 C2 C1 125.9(3) . . ?
C3 C2 C1 126.4(3) . . ?
C13 C12 C17 120.1(4) . . ?
C13 C12 O2 120.7(3) . . ?
C17 C12 O2 119.3(3) . . ?
C6 C11 C10 120.0(4) . . ?
C6 C11 O2 120.4(3) . . ?
C10 C11 O2 119.7(4) . . ?
C15 C14 C13 115.6(3) . . ?
C15 C14 C18 122.0(4) . . ?
C13 C14 C18 122.4(4) . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C3 C4 N1 108.4(3) . . ?
C3 C4 H4 125.8 . . ?
N1 C4 H4 125.8 . . ?
O1 C1 C2 124.6(4) . . ?
O1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C11 C6 C7 118.7(3) . . ?
C11 C6 C5 119.9(3) . . ?
C7 C6 C5 121.4(3) . . ?
C16 C15 C14 123.5(4) . . ?
C16 C15 Cl1 116.9(3) . . ?
C14 C15 Cl1 119.6(3) . . ?
C4 C3 C2 107.8(3) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
C12 C13 C14 122.0(4) . . ?
C12 C13 Cl2 118.1(3) . . ?
C14 C13 Cl2 119.9(3) . . ?
F1 C10 C9 120.1(4) . . ?
F1 C10 C11 118.7(4) . . ?
C9 C10 C11 121.2(4) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?

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
C5 N1 C17 C16 -135.3(4) . . . . ?
C4 N1 C17 C16 41.7(5) . . . . ?
C5 N1 C17 C12 44.0(5) . . . . ?
C4 N1 C17 C12 -139.0(4) . . . . ?
C12 C17 C16 C15 0.4(5) . . . . ?
N1 C17 C16 C15 179.7(3) . . . . ?
C4 N1 C5 C2 1.1(4) . . . . ?
C17 N1 C5 C2 178.5(3) . . . . ?
C4 N1 C5 C6 -178.2(3) . . . . ?
C17 N1 C5 C6 -0.8(5) . . . . ?
N1 C5 C2 C3 -0.6(4) . . . . ?
C6 C5 C2 C3 178.7(4) . . . . ?
N1 C5 C2 C1 175.0(3) . . . . ?
C6 C5 C2 C1 -5.8(6) . . . . ?
C16 C17 C12 C13 -3.1(5) . . . . ?
N1 C17 C12 C13 177.6(3) . . . . ?
C16 C17 C12 O2 177.0(3) . . . . ?
N1 C17 C12 O2 -2.3(5) . . . . ?
C11 O2 C12 C13 109.7(4) . . . . ?
C11 O2 C12 C17 -70.4(4) . . . . ?
C12 O2 C11 C6 70.0(4) . . . . ?
C12 O2 C11 C10 -110.4(4) . . . . ?
C5 N1 C4 C3 -1.3(4) . . . . ?
C17 N1 C4 C3 -178.7(3) . . . . ?
C5 C2 C1 O1 -177.6(3) . . . . ?
C3 C2 C1 O1 -2.9(6) . . . . ?
C10 C11 C6 C7 4.0(5) . . . . ?
O2 C11 C6 C7 -176.5(3) . . . . ?
C10 C11 C6 C5 -176.2(3) . . . . ?
O2 C11 C6 C5 3.4(5) . . . . ?
C8 C7 C6 C11 -2.1(5) . . . . ?
C8 C7 C6 C5 178.0(3) . . . . ?
N1 C5 C6 C11 -43.5(5) . . . . ?
C2 C5 C6 C11 137.3(4) . . . . ?
N1 C5 C6 C7 136.4(4) . . . . ?
C2 C5 C6 C7 -42.8(6) . . . . ?
C17 C16 C15 C14 1.9(5) . . . . ?
C17 C16 C15 Cl1 -176.6(3) . . . . ?
C13 C14 C15 C16 -1.3(5) . . . . ?
C18 C14 C15 C16 179.2(4) . . . . ?
C13 C14 C15 Cl1 177.2(3) . . . . ?
C18 C14 C15 Cl1 -2.4(5) . . . . ?
N1 C4 C3 C2 0.9(4) . . . . ?
C5 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 -175.7(4) . . . . ?
C17 C12 C13 C14 3.8(6) . . . . ?
O2 C12 C13 C14 -176.3(3) . . . . ?
C17 C12 C13 Cl2 -176.9(3) . . . . ?
O2 C12 C13 Cl2 3.0(5) . . . . ?
C15 C14 C13 C12 -1.6(6) . . . . ?
C18 C14 C13 C12 177.9(4) . . . . ?
C15 C14 C13 Cl2 179.1(3) . . . . ?
C18 C14 C13 Cl2 -1.4(5) . . . . ?
C6 C11 C10 F1 177.0(4) . . . . ?
O2 C11 C10 F1 -2.6(6) . . . . ?
C6 C11 C10 C9 -3.6(6) . . . . ?
O2 C11 C10 C9 176.8(4) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
C7 C8 C9 C10 0.6(7) . . . . ?
F1 C10 C9 C8 -179.4(4) . . . . ?
C11 C10 C9 C8 1.3(7) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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 1573098'
_audit_update_record             
;
2017-09-07 deposited with the CCDC.
2018-11-06 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         'C17 H9 F I N O2'
_chemical_formula_sum            'C17 H9 F I N O2'
_chemical_formula_weight         405.15

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   17.5729(13)
_cell_length_b                   9.1432(10)
_cell_length_c                   17.8218(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2863.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2367
_cell_measurement_theta_min      4.1060
_cell_measurement_theta_max      28.8790

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.254
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56010
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 6.1049
_diffrn_reflns_number            7316
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.946
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2808
_reflns_number_gt                2081
_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       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'
_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     
'w=1/[σ²(Fo²)+(0.0363P)²+3.3228P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00064(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2808
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.002
_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 0.21450(2) 0.41946(5) 0.40205(2) 0.05007(18) Uani 1 1 d . . . . .
C15 C 0.0231(3) 0.0898(6) 0.4005(3) 0.0415(13) Uani 1 1 d . . . . .
H15 H 0.033268 0.021842 0.363004 0.050 Uiso 1 1 calc R U . . .
O2 O -0.02325(18) 0.3812(3) 0.57256(17) 0.0334(7) Uani 1 1 d . . . . .
C12 C -0.0075(3) 0.2871(5) 0.5122(2) 0.0302(10) Uani 1 1 d . . . . .
C1 C 0.2172(3) 0.4144(7) 0.7163(3) 0.0525(15) Uani 1 1 d . . . . .
H1 H 0.183271 0.390673 0.754472 0.063 Uiso 1 1 calc R U . . .
C13 C 0.0669(3) 0.2509(5) 0.4966(2) 0.0295(10) Uani 1 1 d . . . . .
C14 C 0.0826(3) 0.1498(5) 0.4414(3) 0.0359(11) Uani 1 1 d . . . . .
H14 H 0.132523 0.122044 0.431711 0.043 Uiso 1 1 calc R U . . .
C17 C -0.0664(3) 0.2281(6) 0.4714(3) 0.0395(12) Uani 1 1 d . . . . .
H17 H -0.116467 0.254320 0.481750 0.047 Uiso 1 1 calc R U . . .
C16 C -0.0507(3) 0.1303(6) 0.4153(3) 0.0449(14) Uani 1 1 d . . . . .
H16 H -0.090152 0.091079 0.386988 0.054 Uiso 1 1 calc R U . . .
C6 C 0.0619(3) 0.2689(5) 0.6618(2) 0.0321(11) Uani 1 1 d . . . . .
N1 N 0.1266(2) 0.3164(4) 0.5403(2) 0.0326(9) Uani 1 1 d . . . . .
C3 C 0.2361(3) 0.4164(7) 0.5732(3) 0.0493(14) Uani 1 1 d . . . . .
H3 H 0.283754 0.460419 0.571378 0.059 Uiso 1 1 calc R U . . .
C4 C 0.1937(3) 0.3766(6) 0.5138(3) 0.0398(12) Uani 1 1 d . . . . .
C7 C 0.0701(3) 0.1887(6) 0.7282(3) 0.0412(12) Uani 1 1 d . . . . .
H7 H 0.118344 0.157944 0.742819 0.049 Uiso 1 1 calc R U . . .
F1 F -0.1232(2) 0.1690(4) 0.79301(19) 0.0704(10) Uani 1 1 d . . . . .
C9 C -0.0620(3) 0.1997(6) 0.7496(3) 0.0452(13) Uani 1 1 d . . . . .
C2 C 0.1948(3) 0.3791(6) 0.6395(3) 0.0409(13) Uani 1 1 d . . . . .
C5 C 0.1275(3) 0.3182(5) 0.6173(2) 0.0325(11) Uani 1 1 d . . . . .
C11 C -0.0115(3) 0.3061(5) 0.6400(2) 0.0295(10) Uani 1 1 d . . . . .
C8 C 0.0083(4) 0.1545(6) 0.7721(3) 0.0463(14) Uani 1 1 d . . . . .
H8 H 0.014400 0.101611 0.816272 0.056 Uiso 1 1 calc R U . . .
C10 C -0.0742(3) 0.2736(5) 0.6835(3) 0.0384(12) Uani 1 1 d . . . . .
H10 H -0.122960 0.300723 0.668671 0.046 Uiso 1 1 calc R U . . .
O1 O 0.2766(2) 0.4721(6) 0.7343(2) 0.0694(13) 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 C4 2.063(5) . ?
C15 C16 1.374(8) . ?
C15 C14 1.387(7) . ?
C15 H15 0.9300 . ?
O2 C11 1.400(5) . ?
O2 C12 1.405(5) . ?
C12 C17 1.375(7) . ?
C12 C13 1.379(7) . ?
C1 O1 1.213(6) . ?
C1 C2 1.460(7) . ?
C1 H1 0.9300 . ?
C13 C14 1.376(7) . ?
C13 N1 1.437(6) . ?
C14 H14 0.9300 . ?
C17 C16 1.369(7) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C6 C11 1.388(6) . ?
C6 C7 1.399(7) . ?
C6 C5 1.471(6) . ?
N1 C5 1.372(5) . ?
N1 C4 1.383(6) . ?
C3 C4 1.345(7) . ?
C3 C2 1.429(8) . ?
C3 H3 0.9300 . ?
C7 C8 1.375(8) . ?
C7 H7 0.9300 . ?
F1 C9 1.354(6) . ?
C9 C8 1.365(8) . ?
C9 C10 1.374(7) . ?
C2 C5 1.366(7) . ?
C11 C10 1.380(6) . ?
C8 H8 0.9300 . ?
C10 H10 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
C16 C15 C14 120.2(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C11 O2 C12 109.2(3) . . ?
C17 C12 C13 120.9(4) . . ?
C17 C12 O2 119.8(4) . . ?
C13 C12 O2 119.2(4) . . ?
O1 C1 C2 125.2(6) . . ?
O1 C1 H1 117.4 . . ?
C2 C1 H1 117.4 . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 N1 121.4(4) . . ?
C12 C13 N1 118.9(4) . . ?
C13 C14 C15 119.4(5) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C17 C12 119.3(5) . . ?
C16 C17 H17 120.3 . . ?
C12 C17 H17 120.3 . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C11 C6 C7 117.5(4) . . ?
C11 C6 C5 120.2(4) . . ?
C7 C6 C5 122.3(4) . . ?
C5 N1 C4 109.1(4) . . ?
C5 N1 C13 123.7(4) . . ?
C4 N1 C13 127.0(4) . . ?
C4 C3 C2 107.8(5) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
C3 C4 N1 108.1(5) . . ?
C3 C4 I1 127.6(4) . . ?
N1 C4 I1 123.8(3) . . ?
C8 C7 C6 121.2(5) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
F1 C9 C8 119.3(5) . . ?
F1 C9 C10 117.9(5) . . ?
C8 C9 C10 122.8(5) . . ?
C5 C2 C3 107.2(4) . . ?
C5 C2 C1 126.6(5) . . ?
C3 C2 C1 125.9(5) . . ?
C2 C5 N1 107.8(4) . . ?
C2 C5 C6 130.3(4) . . ?
N1 C5 C6 121.8(4) . . ?
C10 C11 C6 122.1(4) . . ?
C10 C11 O2 118.0(4) . . ?
C6 C11 O2 119.8(4) . . ?
C9 C8 C7 118.7(5) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C9 C10 C11 117.6(5) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?

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
C11 O2 C12 C17 104.8(5) . . . . ?
C11 O2 C12 C13 -72.7(5) . . . . ?
C17 C12 C13 C14 -2.7(7) . . . . ?
O2 C12 C13 C14 174.8(4) . . . . ?
C17 C12 C13 N1 179.5(4) . . . . ?
O2 C12 C13 N1 -3.0(6) . . . . ?
C12 C13 C14 C15 2.3(7) . . . . ?
N1 C13 C14 C15 -179.9(4) . . . . ?
C16 C15 C14 C13 -0.4(7) . . . . ?
C13 C12 C17 C16 1.1(7) . . . . ?
O2 C12 C17 C16 -176.4(4) . . . . ?
C12 C17 C16 C15 0.9(8) . . . . ?
C14 C15 C16 C17 -1.3(8) . . . . ?
C14 C13 N1 C5 -127.3(5) . . . . ?
C12 C13 N1 C5 50.5(6) . . . . ?
C14 C13 N1 C4 47.5(7) . . . . ?
C12 C13 N1 C4 -134.6(5) . . . . ?
C2 C3 C4 N1 0.5(7) . . . . ?
C2 C3 C4 I1 172.7(4) . . . . ?
C5 N1 C4 C3 -0.3(6) . . . . ?
C13 N1 C4 C3 -175.7(5) . . . . ?
C5 N1 C4 I1 -172.9(4) . . . . ?
C13 N1 C4 I1 11.6(7) . . . . ?
C11 C6 C7 C8 -3.2(7) . . . . ?
C5 C6 C7 C8 174.4(5) . . . . ?
C4 C3 C2 C5 -0.5(7) . . . . ?
C4 C3 C2 C1 -174.6(6) . . . . ?
O1 C1 C2 C5 -177.9(6) . . . . ?
O1 C1 C2 C3 -5.0(10) . . . . ?
C3 C2 C5 N1 0.3(6) . . . . ?
C1 C2 C5 N1 174.3(5) . . . . ?
C3 C2 C5 C6 -175.7(5) . . . . ?
C1 C2 C5 C6 -1.7(9) . . . . ?
C4 N1 C5 C2 0.0(6) . . . . ?
C13 N1 C5 C2 175.6(4) . . . . ?
C4 N1 C5 C6 176.4(5) . . . . ?
C13 N1 C5 C6 -7.9(7) . . . . ?
C11 C6 C5 C2 134.2(6) . . . . ?
C7 C6 C5 C2 -43.4(8) . . . . ?
C11 C6 C5 N1 -41.4(7) . . . . ?
C7 C6 C5 N1 141.0(5) . . . . ?
C7 C6 C11 C10 3.6(7) . . . . ?
C5 C6 C11 C10 -174.1(4) . . . . ?
C7 C6 C11 O2 -177.4(4) . . . . ?
C5 C6 C11 O2 4.9(7) . . . . ?
C12 O2 C11 C10 -111.1(5) . . . . ?
C12 O2 C11 C6 69.9(5) . . . . ?
F1 C9 C8 C7 -178.9(5) . . . . ?
C10 C9 C8 C7 2.3(8) . . . . ?
C6 C7 C8 C9 0.4(8) . . . . ?
F1 C9 C10 C11 179.2(4) . . . . ?
C8 C9 C10 C11 -2.0(8) . . . . ?
C6 C11 C10 C9 -1.1(7) . . . . ?
O2 C11 C10 C9 179.9(4) . . . . ?

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.093



