# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_86711
_database_code_depnum_ccdc_archive 'CCDC 1833356'
loop_
_audit_author_name
_audit_author_address
'Bella Chan'
;The Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2018-03-29 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        7-fluoro-1,3-dimethyl-9H-fluorene
_chemical_name_common            ?
_chemical_melting_point          378.7-380.4
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 F'
_chemical_formula_weight         212.25

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.5004(7)
_cell_length_b                   5.6062(2)
_cell_length_c                   15.1666(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.7377(15)
_cell_angle_gamma                90
_cell_volume                     1110.13(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    164
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5841
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26329
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.337
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2012
_reflns_number_gt                1569
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0618P)²+0.3204P] 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         2012
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.27311(9) 0.0383(2) -0.06388(8) 0.0795(4) Uani 1 1 d . . . . .
C1 C -0.14701(15) 0.4088(4) 0.20760(14) 0.0629(5) Uani 1 1 d . . . . .
H1A H -0.1891 0.4153 0.2499 0.094 Uiso 1 1 calc R U . . .
H1B H -0.1129 0.5591 0.2075 0.094 Uiso 1 1 calc R U . . .
H1C H -0.1891 0.3763 0.1476 0.094 Uiso 1 1 calc R U . . .
C2 C -0.06863(12) 0.2144(3) 0.23543(12) 0.0475(4) Uani 1 1 d . . . . .
C3 C -0.06563(13) 0.0712(3) 0.31133(12) 0.0513(5) Uani 1 1 d . . . . .
H3A H -0.1122 0.1016 0.3458 0.062 Uiso 1 1 calc R U . . .
C4 C 0.00375(14) -0.1146(3) 0.33790(12) 0.0516(5) Uani 1 1 d . . . . .
C5 C 0.00127(18) -0.2667(4) 0.41920(14) 0.0727(6) Uani 1 1 d . . . . .
H5A H -0.0512 -0.2094 0.4463 0.109 Uiso 1 1 calc R U . . .
H5B H -0.0131 -0.4290 0.4000 0.109 Uiso 1 1 calc R U . . .
H5C H 0.0665 -0.2587 0.4631 0.109 Uiso 1 1 calc R U . . .
C6 C 0.07350(13) -0.1619(3) 0.28685(12) 0.0498(4) Uani 1 1 d . . . . .
H6A H 0.1205 -0.2856 0.3033 0.060 Uiso 1 1 calc R U . . .
C7 C 0.07244(11) -0.0231(3) 0.21129(11) 0.0423(4) Uani 1 1 d . . . . .
C8 C 0.13556(12) -0.0355(3) 0.14546(11) 0.0428(4) Uani 1 1 d . . . . .
C9 C 0.21283(13) -0.1925(3) 0.13854(13) 0.0521(5) Uani 1 1 d . . . . .
H9A H 0.2332 -0.3139 0.1811 0.063 Uiso 1 1 calc R U . . .
C10 C 0.25917(13) -0.1657(3) 0.06718(14) 0.0574(5) Uani 1 1 d . . . . .
H10A H 0.3109 -0.2689 0.0611 0.069 Uiso 1 1 calc R U . . .
C11 C 0.22731(14) 0.0150(4) 0.00619(13) 0.0554(5) Uani 1 1 d . . . . .
C12 C 0.15170(13) 0.1731(3) 0.01086(12) 0.0527(5) Uani 1 1 d . . . . .
H12A H 0.1323 0.2942 -0.0320 0.063 Uiso 1 1 calc R U . . .
C13 C 0.10534(12) 0.1467(3) 0.08123(11) 0.0435(4) Uani 1 1 d . . . . .
C14 C 0.01913(13) 0.2884(3) 0.10268(12) 0.0465(4) Uani 1 1 d . . . . .
H14A H 0.0386 0.4538 0.1155 0.056 Uiso 1 1 calc R U . . .
H14B H -0.0421 0.2817 0.0527 0.056 Uiso 1 1 calc R U . . .
C15 C 0.00293(12) 0.1649(3) 0.18596(11) 0.0434(4) 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
F1 C11 1.365(2) . ?
C1 C2 1.503(3) . ?
C2 C15 1.393(2) . ?
C2 C3 1.396(2) . ?
C3 C4 1.390(3) . ?
C4 C6 1.388(2) . ?
C4 C5 1.507(3) . ?
C6 C7 1.382(2) . ?
C7 C15 1.399(2) . ?
C7 C8 1.470(2) . ?
C8 C9 1.389(2) . ?
C8 C13 1.398(2) . ?
C9 C10 1.389(2) . ?
C10 C11 1.366(3) . ?
C11 C12 1.367(3) . ?
C12 C13 1.376(2) . ?
C13 C14 1.511(2) . ?
C14 C15 1.504(2) . ?

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
C15 C2 C3 116.80(16) . . ?
C15 C2 C1 121.90(16) . . ?
C3 C2 C1 121.29(16) . . ?
C4 C3 C2 123.10(16) . . ?
C6 C4 C3 118.93(16) . . ?
C6 C4 C5 120.53(18) . . ?
C3 C4 C5 120.52(17) . . ?
C7 C6 C4 119.32(17) . . ?
C6 C7 C15 121.10(15) . . ?
C6 C7 C8 130.64(15) . . ?
C15 C7 C8 108.26(14) . . ?
C9 C8 C13 120.11(15) . . ?
C9 C8 C7 131.09(15) . . ?
C13 C8 C7 108.78(14) . . ?
C10 C9 C8 119.07(17) . . ?
C11 C10 C9 118.77(16) . . ?
F1 C11 C10 118.11(16) . . ?
F1 C11 C12 118.06(17) . . ?
C10 C11 C12 123.83(17) . . ?
C11 C12 C13 117.59(17) . . ?
C12 C13 C8 120.63(15) . . ?
C12 C13 C14 129.60(15) . . ?
C8 C13 C14 109.76(14) . . ?
C15 C14 C13 102.90(13) . . ?
C2 C15 C7 120.73(15) . . ?
C2 C15 C14 128.98(15) . . ?
C7 C15 C14 110.28(14) . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate, hexane'
