# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_rds582
_database_code_depnum_ccdc_archive 'CCDC 1553660'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            C
_chemical_formula_moiety         'C13 H12 Cl F6 N O'
_chemical_formula_sum            'C13 H12 Cl F6 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         347.69

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.6263(6)
_cell_length_b                   16.9562(13)
_cell_length_c                   10.8430(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.648(4)
_cell_angle_gamma                90
_cell_volume                     1400.64(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    328
_cell_measurement_theta_min      3.9492
_cell_measurement_theta_max      33.6018
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.397
_exptl_crystal_size_min          0.332
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704

_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            54325
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         36.45
_diffrn_reflns_theta_full        36.45
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             6844
_reflns_number_gt                5844
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0887
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         6844
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.3763P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 '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'
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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 786)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.06334(2) 0.59161(2) 0.95250(2) 0.01827(5) Uani d . . . 1 . .
F F1 -0.02829(9) 0.72173(3) 0.54611(6) 0.03143(13) Uani d . . . 1 . .
F F2 -0.02588(8) 0.72702(3) 0.74377(6) 0.03009(14) Uani d . . . 1 . .
F F3 -0.27084(7) 0.72001(3) 0.63829(7) 0.02915(13) Uani d . . . 1 . .
F F4 0.21895(8) 0.36524(3) 0.68055(6) 0.02891(13) Uani d . . . 1 . .
F F5 0.21523(8) 0.42495(4) 0.85526(6) 0.03280(14) Uani d . . . 1 . .
F F6 0.36569(6) 0.47131(3) 0.70980(6) 0.02299(11) Uani d . . . 1 . .
O O1 0.31277(7) 0.63976(3) 0.66938(5) 0.01546(10) Uani d . . . 1 . .
N N1 0.23834(7) 0.61603(4) 0.86725(5) 0.01186(9) Uani d . . . 1 . .
C C1 0.05252(8) 0.56541(4) 0.69423(6) 0.01134(10) Uani d . . . 1 . .
C C2 -0.09881(9) 0.60461(4) 0.64902(6) 0.01304(11) Uani d . . . 1 . .
C C3 -0.24451(9) 0.56257(5) 0.60255(7) 0.01657(12) Uani d . . . 1 . .
H H3 -0.3471 0.59 0.5738 0.02 Uiso calc U . R 1 . .
C C4 -0.24004(10) 0.48099(5) 0.59826(8) 0.01837(13) Uani d . . . 1 . .
H H4 -0.3396 0.4523 0.5671 0.022 Uiso calc U . R 1 . .
C C5 -0.08937(10) 0.44129(4) 0.63964(7) 0.01688(12) Uani d . . . 1 . .
H H5 -0.0853 0.3854 0.6355 0.02 Uiso calc U . R 1 . .
C C6 0.05571(9) 0.48298(4) 0.68721(6) 0.01276(11) Uani d . . . 1 . .
C C7 0.21230(8) 0.61148(4) 0.74185(6) 0.01134(10) Uani d . . . 1 . .
C C8 -0.10581(10) 0.69327(4) 0.64503(8) 0.01766(13) Uani d . . . 1 . .
C C9 0.21378(10) 0.43636(4) 0.73311(7) 0.01593(12) Uani d . . . 1 . .
C C10 0.38949(8) 0.66004(4) 0.93100(6) 0.01218(10) Uani d . . . 1 . .
C C11 0.55951(10) 0.62246(6) 0.88981(8) 0.02160(15) Uani d . . . 1 . .
H H11A 0.5638 0.5671 0.9156 0.032 Uiso calc U . R 1 . .
H H11B 0.6604 0.6507 0.9278 0.032 Uiso calc U . R 1 . .
H H11C 0.5633 0.6256 0.7997 0.032 Uiso calc U . R 1 . .
C C12 0.38191(10) 0.65082(5) 1.07056(7) 0.01736(12) Uani d . . . 1 . .
H H12A 0.2768 0.6772 1.0989 0.026 Uiso calc U . R 1 . .
H H12B 0.4866 0.6747 1.1109 0.026 Uiso calc U . R 1 . .
H H12C 0.3775 0.5947 1.0916 0.026 Uiso calc U . R 1 . .
C C13 0.37696(12) 0.74717(5) 0.89683(8) 0.02183(15) Uani d . . . 1 . .
H H13A 0.3851 0.7531 0.8074 0.033 Uiso calc U . R 1 . .
H H13B 0.4732 0.7761 0.9393 0.033 Uiso calc U . R 1 . .
H H13C 0.2644 0.7683 0.9219 0.033 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 N1 . 1.7091(6) ?
F1 C8 . 1.3384(10) ?
F2 C8 . 1.3361(10) ?
F3 C8 . 1.3366(9) ?
F4 C9 . 1.3351(9) ?
F5 C9 . 1.3381(10) ?
F6 C9 . 1.3358(9) ?
O1 C7 . 1.2207(8) ?
N1 C7 . 1.3673(9) ?
N1 C10 . 1.5132(9) ?
C1 C6 . 1.4001(10) ?
C1 C2 . 1.4006(9) ?
C1 C7 . 1.5177(9) ?
C2 C3 . 1.3946(10) ?
C2 C8 . 1.5048(11) ?
C3 C4 . 1.3847(12) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3882(11) ?
C4 H4 . 0.95 ?
C5 C6 . 1.3918(10) ?
C5 H5 . 0.95 ?
C6 C9 . 1.5068(10) ?
C10 C13 . 1.5250(11) ?
C10 C12 . 1.5251(10) ?
C10 C11 . 1.5298(10) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C10 . . 123.69(5) ?
C7 N1 Cl1 . . 116.30(5) ?
C10 N1 Cl1 . . 118.03(4) ?
C6 C1 C2 . . 118.09(6) ?
C6 C1 C7 . . 121.11(6) ?
C2 C1 C7 . . 120.69(6) ?
C3 C2 C1 . . 120.91(7) ?
C3 C2 C8 . . 118.27(6) ?
C1 C2 C8 . . 120.78(6) ?
C4 C3 C2 . . 120.16(7) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 119.66(7) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 120.36(7) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 120.78(6) ?
C5 C6 C9 . . 117.78(6) ?
C1 C6 C9 . . 121.43(6) ?
O1 C7 N1 . . 123.46(6) ?
O1 C7 C1 . . 120.08(6) ?
N1 C7 C1 . . 116.41(6) ?
F2 C8 F3 . . 106.99(7) ?
F2 C8 F1 . . 106.60(7) ?
F3 C8 F1 . . 106.47(7) ?
F2 C8 C2 . . 113.00(6) ?
F3 C8 C2 . . 111.87(6) ?
F1 C8 C2 . . 111.52(6) ?
F4 C9 F6 . . 106.08(6) ?
F4 C9 F5 . . 107.03(7) ?
F6 C9 F5 . . 106.49(7) ?
F4 C9 C6 . . 111.83(6) ?
F6 C9 C6 . . 113.10(6) ?
F5 C9 C6 . . 111.88(6) ?
N1 C10 C13 . . 109.20(6) ?
N1 C10 C12 . . 109.86(5) ?
C13 C10 C12 . . 109.60(6) ?
N1 C10 C11 . . 107.42(6) ?
C13 C10 C11 . . 112.15(7) ?
C12 C10 C11 . . 108.57(6) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 2.32(10) ?
C7 C1 C2 C3 . . . . 178.52(6) ?
C6 C1 C2 C8 . . . . -175.39(6) ?
C7 C1 C2 C8 . . . . 0.80(10) ?
C1 C2 C3 C4 . . . . -1.29(11) ?
C8 C2 C3 C4 . . . . 176.49(7) ?
C2 C3 C4 C5 . . . . -0.45(12) ?
C3 C4 C5 C6 . . . . 1.08(12) ?
C4 C5 C6 C1 . . . . 0.01(11) ?
C4 C5 C6 C9 . . . . 178.71(7) ?
C2 C1 C6 C5 . . . . -1.68(10) ?
C7 C1 C6 C5 . . . . -177.86(6) ?
C2 C1 C6 C9 . . . . 179.66(6) ?
C7 C1 C6 C9 . . . . 3.48(10) ?
C10 N1 C7 O1 . . . . 3.17(11) ?
Cl1 N1 C7 O1 . . . . 166.78(6) ?
C10 N1 C7 C1 . . . . -179.43(6) ?
Cl1 N1 C7 C1 . . . . -15.82(8) ?
C6 C1 C7 O1 . . . . 96.61(8) ?
C2 C1 C7 O1 . . . . -79.47(9) ?
C6 C1 C7 N1 . . . . -80.89(8) ?
C2 C1 C7 N1 . . . . 103.03(8) ?
C3 C2 C8 F2 . . . . 143.28(7) ?
C1 C2 C8 F2 . . . . -38.94(10) ?
C3 C2 C8 F3 . . . . 22.46(10) ?
C1 C2 C8 F3 . . . . -159.76(7) ?
C3 C2 C8 F1 . . . . -96.66(8) ?
C1 C2 C8 F1 . . . . 81.11(9) ?
C5 C6 C9 F4 . . . . 23.78(9) ?
C1 C6 C9 F4 . . . . -157.53(7) ?
C5 C6 C9 F6 . . . . 143.47(7) ?
C1 C6 C9 F6 . . . . -37.83(9) ?
C5 C6 C9 F5 . . . . -96.28(8) ?
C1 C6 C9 F5 . . . . 82.42(9) ?
C7 N1 C10 C13 . . . . 61.59(8) ?
Cl1 N1 C10 C13 . . . . -101.76(6) ?
C7 N1 C10 C12 . . . . -178.18(6) ?
Cl1 N1 C10 C12 . . . . 18.47(7) ?
C7 N1 C10 C11 . . . . -60.26(9) ?
Cl1 N1 C10 C11 . . . . 136.40(6) ?

