# 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_shelxla_a_a_a
_database_code_depnum_ccdc_archive 'CCDC 1825223'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 F3 O'
_chemical_formula_weight         290.27

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'
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'

_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                   12.9659(17)
_cell_length_b                   8.4037(11)
_cell_length_c                   12.8931(17)
_cell_angle_alpha                90
_cell_angle_beta                 113.1710(10)
_cell_angle_gamma                90
_cell_volume                     1291.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    3580
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      27.41

_exptl_crystal_description       plate

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   ?

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            7320
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.708
_diffrn_reflns_theta_max         28.728
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3072
_reflns_number_gt                2647
_reflns_threshold_expression     'I > 2σ'
_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       'APEX2 '

_computing_cell_refinement       'APEX2 '

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'

_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0360P)²+0.5955P] 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         3072
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_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 0.37815(10) 0.29766(15) 0.55481(10) 0.0169(2) Uani 1 1 d . . . . .
C2 C 0.42635(11) 0.20097(15) 0.49866(11) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.3818 0.1242 0.4460 0.024 Uiso 1 1 calc R U . . .
C3 C 0.53960(11) 0.21628(16) 0.51934(12) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.5722 0.1504 0.4805 0.029 Uiso 1 1 calc R U . . .
C4 C 0.60485(11) 0.32761(17) 0.59663(12) 0.0259(3) Uani 1 1 d . . . . .
H4 H 0.6825 0.3369 0.6118 0.031 Uiso 1 1 calc R U . . .
C5 C 0.55660(11) 0.42537(17) 0.65165(11) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.6017 0.5016 0.7045 0.029 Uiso 1 1 calc R U . . .
C6 C 0.44271(11) 0.41363(15) 0.63066(10) 0.0201(3) Uani 1 1 d . . . . .
C7 C 0.38946(12) 0.53032(18) 0.68378(12) 0.0270(3) Uani 1 1 d . . . . .
H7A H 0.3771 0.6321 0.6419 0.032 Uiso 1 1 calc R U . . .
H7B H 0.4428 0.5512 0.7621 0.032 Uiso 1 1 calc R U . . .
C8 C 0.27678(12) 0.47564(17) 0.68635(11) 0.0255(3) Uani 1 1 d . . . . .
H8 H 0.2841 0.4798 0.7664 0.031 Uiso 1 1 calc R U . . .
C9 C 0.17728(12) 0.57731(18) 0.61657(12) 0.0276(3) Uani 1 1 d . . . . .
H9A H 0.1111 0.5466 0.6323 0.033 Uiso 1 1 calc R U . . .
H9B H 0.1941 0.6906 0.6374 0.033 Uiso 1 1 calc R U . . .
C10 C 0.15133(10) 0.55581(16) 0.49233(11) 0.0206(3) Uani 1 1 d . . . . .
C11 C 0.09341(11) 0.67322(17) 0.41427(12) 0.0254(3) Uani 1 1 d . . . . .
H11 H 0.0683 0.7660 0.4395 0.030 Uiso 1 1 calc R U . . .
C12 C 0.07197(11) 0.65663(17) 0.30078(12) 0.0253(3) Uani 1 1 d . . . . .
H12 H 0.0313 0.7365 0.2486 0.030 Uiso 1 1 calc R U . . .
C13 C 0.11013(10) 0.52313(17) 0.26371(11) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.0958 0.5116 0.1859 0.027 Uiso 1 1 calc R U . . .
C14 C 0.16926(10) 0.40608(15) 0.33984(10) 0.0179(2) Uani 1 1 d . . . . .
H14 H 0.1974 0.3164 0.3144 0.021 Uiso 1 1 calc R U . . .
C15 C 0.18767(10) 0.41956(15) 0.45423(10) 0.0163(2) Uani 1 1 d . . . . .
C16 C 0.25524(10) 0.29245(15) 0.53909(10) 0.0168(2) Uani 1 1 d . . . . .
C17 C 0.20052(10) 0.12771(16) 0.50687(10) 0.0199(3) Uani 1 1 d . . . . .
F1 F 0.25727(7) 0.01681(10) 0.58277(7) 0.0285(2) Uani 1 1 d . . . . .
F2 F 0.19352(6) 0.07486(9) 0.40624(6) 0.02370(18) Uani 1 1 d . . . . .
F3 F 0.09527(6) 0.12846(10) 0.50222(7) 0.02696(19) Uani 1 1 d . . . . .
O1 O 0.25062(8) 0.31401(11) 0.64739(7) 0.0228(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 1.3896(18) . ?
C1 C6 1.4010(17) . ?
C1 C16 1.5259(16) . ?
C2 C3 1.3912(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3960(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.5098(19) . ?
C7 C8 1.544(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.4416(17) . ?
C8 C9 1.513(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.5125(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3984(19) . ?
C10 C15 1.3988(17) . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3881(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.4028(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.5335(17) . ?
C16 O1 1.4324(14) . ?
C16 C17 1.5364(17) . ?
C17 F2 1.3402(15) . ?
C17 F1 1.3421(15) . ?
C17 F3 1.3423(14) . ?

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 120.18(11) . . ?
C2 C1 C16 125.05(11) . . ?
C6 C1 C16 114.75(11) . . ?
C1 C2 C3 120.21(12) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.00(13) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.84(12) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.01(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.71(12) . . ?
C5 C6 C7 120.25(12) . . ?
C1 C6 C7 120.94(12) . . ?
C6 C7 C8 114.95(11) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O1 C8 C9 107.23(11) . . ?
O1 C8 C7 111.58(11) . . ?
C9 C8 C7 114.31(12) . . ?
O1 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C7 C8 H8 107.8 . . ?
C10 C9 C8 110.15(11) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C15 118.98(12) . . ?
C11 C10 C9 120.70(12) . . ?
C15 C10 C9 120.29(12) . . ?
C12 C11 C10 121.14(13) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 119.72(12) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.20(12) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.29(12) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.60(11) . . ?
C10 C15 C16 119.76(11) . . ?
C14 C15 C16 120.46(11) . . ?
O1 C16 C1 108.00(9) . . ?
O1 C16 C15 112.09(10) . . ?
C1 C16 C15 110.39(10) . . ?
O1 C16 C17 100.70(9) . . ?
C1 C16 C17 114.13(10) . . ?
C15 C16 C17 111.18(10) . . ?
F2 C17 F1 106.54(11) . . ?
F2 C17 F3 106.14(10) . . ?
F1 C17 F3 106.97(10) . . ?
F2 C17 C16 114.11(10) . . ?
F1 C17 C16 111.48(10) . . ?
F3 C17 C16 111.17(10) . . ?
C16 O1 C8 111.38(9) . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6

