# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_KA129_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1579886'
_audit_update_record             
;
2017-10-13 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H13 Cl F3 N3 O'
_chemical_formula_sum            'C23 H13 Cl F3 N3 O'
_chemical_formula_weight         439.81

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      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                   9.584(5)
_cell_length_b                   9.866(4)
_cell_length_c                   11.366(6)
_cell_angle_alpha                80.384(9)
_cell_angle_beta                 84.059(12)
_cell_angle_gamma                66.028(10)
_cell_volume                     967.5(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.377
_cell_measurement_theta_max      30.438

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.247
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24696
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.281
_diffrn_reflns_theta_max         30.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5909
_reflns_number_gt                4938
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0649P)²+0.2290P] 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         5909
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C1 C -0.08622(14) 0.83940(15) 0.97667(11) 0.0369(2) Uani 1 1 d . . . . .
C2 C 0.01736(15) 0.69205(15) 0.98922(11) 0.0375(3) Uani 1 1 d . . . . .
H2 H 0.0487 0.6401 1.0644 0.045 Uiso 1 1 calc R U . . .
C3 C 0.07359(14) 0.62324(14) 0.88801(11) 0.0363(2) Uani 1 1 d . . . . .
H3 H 0.1451 0.5248 0.8945 0.044 Uiso 1 1 calc R U . . .
C4 C 0.02321(13) 0.70117(13) 0.77676(10) 0.0319(2) Uani 1 1 d . . . . .
C5 C -0.08470(15) 0.84690(14) 0.76584(11) 0.0397(3) Uani 1 1 d . . . . .
H5 H -0.1205 0.8972 0.6912 0.048 Uiso 1 1 calc R U . . .
C6 C -0.13898(16) 0.91724(15) 0.86628(13) 0.0424(3) Uani 1 1 d . . . . .
H6 H -0.2102 1.0159 0.8598 0.051 Uiso 1 1 calc R U . . .
C7 C 0.07094(14) 0.49837(13) 0.66038(10) 0.0328(2) Uani 1 1 d . . . . .
C8 C 0.16904(14) 0.41514(13) 0.56562(10) 0.0313(2) Uani 1 1 d . . . . .
C9 C 0.18138(17) 0.26918(14) 0.56382(12) 0.0397(3) Uani 1 1 d . . . . .
H9 H 0.1196 0.2318 0.6155 0.048 Uiso 1 1 calc R U . . .
C10 C 0.28402(19) 0.18081(15) 0.48620(13) 0.0462(3) Uani 1 1 d . . . . .
H10 H 0.2907 0.0845 0.4843 0.055 Uiso 1 1 calc R U . . .
C11 C 0.37789(19) 0.23648(15) 0.41039(13) 0.0458(3) Uani 1 1 d . . . . .
H11 H 0.4494 0.1755 0.3596 0.055 Uiso 1 1 calc R U . . .
C12 C 0.36667(16) 0.38112(14) 0.40929(11) 0.0391(3) Uani 1 1 d . . . . .
H12 H 0.4302 0.4170 0.3584 0.047 Uiso 1 1 calc R U . . .
C13 C 0.25940(13) 0.47207(12) 0.48512(10) 0.0300(2) Uani 1 1 d . . . . .
C14 C 0.16667(14) 0.69170(13) 0.58786(10) 0.0332(2) Uani 1 1 d . . . . .
C15 C 0.18767(18) 0.82164(15) 0.57602(12) 0.0450(3) Uani 1 1 d . . . . .
H15 H 0.1533 0.8896 0.6309 0.054 Uiso 1 1 calc R U . . .
C16 C 0.29735(14) 0.71859(13) 0.41939(10) 0.0332(2) Uani 1 1 d . . . . .
C17 C 0.36666(13) 0.70616(13) 0.29772(10) 0.0316(2) Uani 1 1 d . . . . .
C18 C 0.30677(15) 0.66496(15) 0.21004(11) 0.0369(3) Uani 1 1 d . . . . .
H18 H 0.2283 0.6317 0.2299 0.044 Uiso 1 1 calc R U . . .
C19 C 0.36384(16) 0.67339(15) 0.09281(11) 0.0380(3) Uani 1 1 d . . . . .
H19 H 0.3233 0.6461 0.0342 0.046 Uiso 1 1 calc R U . . .
C20 C 0.48105(14) 0.72238(13) 0.06317(11) 0.0341(2) Uani 1 1 d . . . . .
C21 C 0.54296(15) 0.76217(15) 0.15038(12) 0.0395(3) Uani 1 1 d . . . . .
H21 H 0.6224 0.7940 0.1304 0.047 Uiso 1 1 calc R U . . .
C22 C 0.48589(14) 0.75420(15) 0.26691(11) 0.0374(3) Uani 1 1 d . . . . .
H22 H 0.5271 0.7810 0.3253 0.045 Uiso 1 1 calc R U . . .
C23 C 0.54014(16) 0.73672(16) -0.06323(12) 0.0422(3) Uani 1 1 d . . . . .
Cl1 Cl -0.15094(5) 0.92983(5) 1.10245(4) 0.05711(12) Uani 1 1 d . . . . .
F1 F 0.68451(11) 0.64095(12) -0.07851(9) 0.0656(3) Uani 1 1 d . . . . .
F2 F 0.53852(13) 0.87254(11) -0.10218(9) 0.0656(3) Uani 1 1 d . . . . .
F3 F 0.45902(13) 0.71164(15) -0.13931(8) 0.0694(3) Uani 1 1 d . . . . .
N1 N 0.08840(12) 0.62756(11) 0.67315(9) 0.0335(2) Uani 1 1 d . . . . .
N2 N 0.23903(11) 0.62147(10) 0.48939(8) 0.03007(19) Uani 1 1 d . . . . .
N3 N 0.26760(15) 0.83726(13) 0.47039(10) 0.0442(3) Uani 1 1 d . . . . .
O1 O -0.01360(12) 0.45356(12) 0.72820(9) 0.0447(2) 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 1.381(2) . ?
C1 C6 1.383(2) . ?
C1 Cl1 1.7371(15) . ?
C2 C3 1.3819(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.3868(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3823(18) . ?
C4 N1 1.4384(16) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.2223(15) . ?
C7 N1 1.3835(16) . ?
C7 C8 1.4754(18) . ?
C8 C9 1.3997(17) . ?
C8 C13 1.4008(16) . ?
C9 C10 1.374(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.3848(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.3894(18) . ?
C12 H12 0.9300 . ?
C13 N2 1.4146(15) . ?
C14 C15 1.3596(17) . ?
C14 N2 1.3862(16) . ?
C14 N1 1.3904(15) . ?
C15 N3 1.3769(18) . ?
C15 H15 0.9300 . ?
C16 N3 1.3073(17) . ?
C16 N2 1.3971(14) . ?
C16 C17 1.4727(17) . ?
C17 C18 1.3897(17) . ?
C17 C22 1.3982(17) . ?
C18 C19 1.3895(18) . ?
C18 H18 0.9300 . ?
C19 C20 1.3848(18) . ?
C19 H19 0.9300 . ?
C20 C21 1.3892(19) . ?
C20 C23 1.4944(19) . ?
C21 C22 1.3820(19) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 F2 1.3335(17) . ?
C23 F3 1.3342(19) . ?
C23 F1 1.3343(17) . ?

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 121.65(12) . . ?
C2 C1 Cl1 119.22(10) . . ?
C6 C1 Cl1 119.13(11) . . ?
C1 C2 C3 118.78(11) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 119.94(12) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.69(11) . . ?
C5 C4 N1 120.99(11) . . ?
C3 C4 N1 118.30(11) . . ?
C6 C5 C4 119.63(11) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.24(12) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O1 C7 N1 121.45(12) . . ?
O1 C7 C8 123.24(11) . . ?
N1 C7 C8 115.17(10) . . ?
C9 C8 C13 119.39(12) . . ?
C9 C8 C7 118.11(11) . . ?
C13 C8 C7 122.26(10) . . ?
C10 C9 C8 120.47(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.52(12) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 121.17(13) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.26(12) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 120.08(11) . . ?
C12 C13 N2 123.17(10) . . ?
C8 C13 N2 116.71(10) . . ?
C15 C14 N2 106.99(10) . . ?
C15 C14 N1 132.73(11) . . ?
N2 C14 N1 120.26(11) . . ?
C14 C15 N3 109.62(11) . . ?
C14 C15 H15 125.2 . . ?
N3 C15 H15 125.2 . . ?
N3 C16 N2 110.86(11) . . ?
N3 C16 C17 121.50(10) . . ?
N2 C16 C17 127.23(10) . . ?
C18 C17 C22 119.31(11) . . ?
C18 C17 C16 122.30(11) . . ?
C22 C17 C16 117.98(11) . . ?
C19 C18 C17 120.14(11) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.03(12) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.30(11) . . ?
C19 C20 C23 120.61(12) . . ?
C21 C20 C23 119.08(12) . . ?
C22 C21 C20 119.67(11) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C17 120.55(12) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
F2 C23 F3 106.21(12) . . ?
F2 C23 F1 105.77(12) . . ?
F3 C23 F1 106.27(13) . . ?
F2 C23 C20 112.69(12) . . ?
F3 C23 C20 112.69(12) . . ?
F1 C23 C20 112.66(12) . . ?
C7 N1 C14 122.25(10) . . ?
C7 N1 C4 120.07(10) . . ?
C14 N1 C4 117.68(10) . . ?
C14 N2 C16 105.51(10) . . ?
C14 N2 C13 120.52(9) . . ?
C16 N2 C13 133.25(10) . . ?
C16 N3 C15 106.99(11) . . ?

_refine_diff_density_max         0.747
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
