# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_200611a_a
_database_code_depnum_ccdc_archive 'CCDC 2013468'
loop_
_audit_author_name
_audit_author_address
'Yichao Gu'
;Tongji University
China
;
_audit_update_record             
;
2020-07-01 deposited with the CCDC.	2020-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 F'
_chemical_formula_weight         226.28

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'
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                   14.697(8)
_cell_length_b                   5.790(3)
_cell_length_c                   14.578(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.759(19)
_cell_angle_gamma                90
_cell_volume                     1199.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    281(2)
_cell_measurement_reflns_used    4977
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   0.5697
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      281(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13101
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.867
_diffrn_reflns_theta_max         25.334
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2173
_reflns_number_gt                1608
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0895P)²+0.3831P] 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-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2173
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
F1 F 0.47166(9) 0.1749(3) 0.61439(10) 0.0728(5) Uani 1 1 d . . . . .
C1 C 0.80923(13) 0.5637(4) 0.49697(14) 0.0472(5) Uani 1 1 d . . . . .
C2 C 0.86518(15) 0.5358(4) 0.43386(16) 0.0567(6) Uani 1 1 d . . . . .
H2 H 0.921776 0.615825 0.444329 0.068 Uiso 1 1 calc R U . . .
C3 C 0.83874(17) 0.3924(5) 0.35619(16) 0.0660(7) Uani 1 1 d . . . . .
H3 H 0.877787 0.375146 0.315485 0.079 Uiso 1 1 calc R U . . .
C4 C 0.75508(16) 0.2752(5) 0.33874(16) 0.0654(7) Uani 1 1 d . . . . .
H4 H 0.736845 0.180391 0.285729 0.078 Uiso 1 1 calc R U . . .
C5 C 0.69806(15) 0.2983(4) 0.40000(15) 0.0555(6) Uani 1 1 d . . . . .
H5 H 0.641407 0.218191 0.387945 0.067 Uiso 1 1 calc R U . . .
C6 C 0.72406(13) 0.4405(4) 0.48009(13) 0.0459(5) Uani 1 1 d . . . . .
C7 C 0.66319(13) 0.4625(4) 0.54671(13) 0.0453(5) Uani 1 1 d . . . . .
C8 C 0.59382(14) 0.3015(4) 0.54978(14) 0.0499(5) Uani 1 1 d . . . . .
H8 H 0.584239 0.173985 0.509662 0.060 Uiso 1 1 calc R U . . .
C9 C 0.53962(14) 0.3334(4) 0.61288(15) 0.0536(6) Uani 1 1 d . . . . .
C10 C 0.55123(16) 0.5162(5) 0.67381(16) 0.0611(6) Uani 1 1 d . . . . .
H10 H 0.513557 0.533220 0.715857 0.073 Uiso 1 1 calc R U . . .
C11 C 0.62035(16) 0.6748(4) 0.67123(16) 0.0600(6) Uani 1 1 d . . . . .
H11 H 0.629517 0.799974 0.712565 0.072 Uiso 1 1 calc R U . . .
C12 C 0.67691(14) 0.6523(4) 0.60811(15) 0.0498(5) Uani 1 1 d . . . . .
C13 C 0.75075(16) 0.8248(4) 0.60248(18) 0.0603(6) Uani 1 1 d . . . . .
H13A H 0.767726 0.911538 0.661300 0.072 Uiso 1 1 calc R U . . .
H13B H 0.724945 0.932636 0.551588 0.072 Uiso 1 1 calc R U . . .
C14 C 0.83945(14) 0.7146(4) 0.58501(15) 0.0506(5) Uani 1 1 d . . . . .
C15 C 0.90668(18) 0.9082(4) 0.5743(2) 0.0707(7) Uani 1 1 d . . . . .
H15A H 0.964094 0.842541 0.566171 0.106 Uiso 1 1 calc R U . . .
H15B H 0.920185 1.003281 0.630103 0.106 Uiso 1 1 calc R U . . .
H15C H 0.878001 1.000521 0.519911 0.106 Uiso 1 1 calc R U . . .
C16 C 0.88814(17) 0.5613(4) 0.66917(16) 0.0624(6) Uani 1 1 d . . . . .
H16A H 0.845775 0.441560 0.677512 0.094 Uiso 1 1 calc R U . . .
H16B H 0.905691 0.653372 0.725694 0.094 Uiso 1 1 calc R U . . .
H16C H 0.943406 0.493060 0.656904 0.094 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
F1 C9 1.361(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.407(3) . ?
C1 C14 1.522(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.484(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.399(3) . ?
C8 C9 1.374(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.492(3) . ?
C13 C14 1.530(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.529(3) . ?
C14 C16 1.535(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 118.4(2) . . ?
C2 C1 C14 122.00(19) . . ?
C6 C1 C14 119.60(18) . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.06(19) . . ?
C5 C6 C7 120.95(18) . . ?
C1 C6 C7 119.99(18) . . ?
C8 C7 C12 119.57(19) . . ?
C8 C7 C6 122.19(19) . . ?
C12 C7 C6 118.24(18) . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
F1 C9 C10 118.91(19) . . ?
F1 C9 C8 118.2(2) . . ?
C10 C9 C8 122.8(2) . . ?
C9 C10 C11 118.1(2) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C10 C11 C12 121.6(2) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C7 118.8(2) . . ?
C11 C12 C13 122.5(2) . . ?
C7 C12 C13 118.61(19) . . ?
C12 C13 C14 113.12(18) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C1 C14 C15 113.08(19) . . ?
C1 C14 C13 107.56(17) . . ?
C15 C14 C13 108.16(19) . . ?
C1 C14 C16 108.57(18) . . ?
C15 C14 C16 108.89(19) . . ?
C13 C14 C16 110.58(19) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
_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 0.3(3) . . . . ?
C14 C1 C2 C3 177.6(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C14 C1 C6 C5 -178.58(18) . . . . ?
C2 C1 C6 C7 178.94(18) . . . . ?
C14 C1 C6 C7 1.5(3) . . . . ?
C5 C6 C7 C8 18.6(3) . . . . ?
C1 C6 C7 C8 -161.48(18) . . . . ?
C5 C6 C7 C12 -161.46(19) . . . . ?
C1 C6 C7 C12 18.5(3) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
C6 C7 C8 C9 -179.62(18) . . . . ?
C7 C8 C9 F1 179.55(17) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
F1 C9 C10 C11 -179.99(19) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?
C10 C11 C12 C13 178.6(2) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C6 C7 C12 C11 -179.86(18) . . . . ?
C8 C7 C12 C13 -179.05(19) . . . . ?
C6 C7 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C14 142.4(2) . . . . ?
C7 C12 C13 C14 -38.5(3) . . . . ?
C2 C1 C14 C15 26.8(3) . . . . ?
C6 C1 C14 C15 -155.87(19) . . . . ?
C2 C1 C14 C13 146.1(2) . . . . ?
C6 C1 C14 C13 -36.5(3) . . . . ?
C2 C1 C14 C16 -94.2(2) . . . . ?
C6 C1 C14 C16 83.2(2) . . . . ?
C12 C13 C14 C1 54.0(2) . . . . ?
C12 C13 C14 C15 176.40(19) . . . . ?
C12 C13 C14 C16 -64.4(2) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.054



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
