# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_8057
_database_code_depnum_ccdc_archive 'CCDC 1939223'
loop_
_audit_author_name
_audit_author_address
'Pradip Nahide' 'University of Pennsylvania'
_audit_update_record             
;
2019-07-08 deposited with the CCDC.	2026-05-27 downloaded from the CCDC.
;

#Crystallographer: Michael R. Gau

_audit_creation_date             2019-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C29 H25 F O'
_chemical_formula_sum            'C29 H25 F O'
_chemical_formula_weight         408.49
_chemical_absolute_configuration syn

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.9195(5)
_cell_length_b                   13.0385(7)
_cell_length_c                   9.2973(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.357(2)
_cell_angle_gamma                90
_cell_volume                     1072.35(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.357
_cell_measurement_theta_min      3.125
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plank
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22247
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.382
_diffrn_reflns_theta_min         3.125
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'CMOS area detector'
_diffrn_measurement_device_type  'Bruker D8QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3655
_reflns_number_total             3940
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       'Bruker APEX3 v2016.1-0'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1629 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3940
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.1873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0847
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual

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 0.14762(17) 0.49709(14) 0.95048(15) 0.0313(4) Uani 1 1 d . . . . .
O1 O 0.60263(19) 0.31619(14) 0.30615(18) 0.0211(4) Uani 1 1 d . . . . .
C1 C 0.4468(3) 0.57962(19) 0.3544(3) 0.0174(5) Uani 1 1 d . . . . .
H1 H 0.484424 0.634011 0.425822 0.021 Uiso 1 1 calc R . . . .
C2 C 0.4379(3) 0.47595(19) 0.4435(2) 0.0164(5) Uani 1 1 d . . . . .
C3 C 0.6006(3) 0.4441(2) 0.4959(3) 0.0178(5) Uani 1 1 d . . . . .
C4 C 0.6847(3) 0.4951(2) 0.6114(2) 0.0209(5) Uani 1 1 d . . . . .
H4 H 0.636376 0.544243 0.665364 0.025 Uiso 1 1 calc R . . . .
C5 C 0.8372(3) 0.4754(2) 0.6486(3) 0.0284(6) Uani 1 1 d . . . . .
H5 H 0.893275 0.511555 0.726432 0.034 Uiso 1 1 calc R . . . .
C6 C 0.9080(3) 0.4025(2) 0.5717(3) 0.0296(7) Uani 1 1 d . . . . .
H6 H 1.012809 0.389136 0.596500 0.036 Uiso 1 1 calc R . . . .
C7 C 0.8262(3) 0.3493(2) 0.4590(3) 0.0242(6) Uani 1 1 d . . . . .
H7 H 0.873765 0.298425 0.407483 0.029 Uiso 1 1 calc R . . . .
C8 C 0.6738(3) 0.37121(19) 0.4222(3) 0.0187(5) Uani 1 1 d . . . . .
C9 C 0.4467(3) 0.3202(2) 0.2800(3) 0.0194(5) Uani 1 1 d . . . . .
C10 C 0.3800(3) 0.2483(2) 0.1823(3) 0.0243(6) Uani 1 1 d . . . . .
H10 H 0.440589 0.200681 0.138164 0.029 Uiso 1 1 calc R . . . .
C11 C 0.2241(3) 0.2467(2) 0.1495(3) 0.0268(6) Uani 1 1 d . . . . .
H11 H 0.177290 0.198323 0.081651 0.032 Uiso 1 1 calc R . . . .
C12 C 0.1365(3) 0.3155(2) 0.2157(3) 0.0237(6) Uani 1 1 d . . . . .
H12 H 0.029504 0.314104 0.193933 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2051(3) 0.3862(2) 0.3136(3) 0.0184(5) Uani 1 1 d . . . . .
H13 H 0.143985 0.432092 0.360086 0.022 Uiso 1 1 calc R . . . .
C14 C 0.3621(3) 0.39180(19) 0.3459(2) 0.0167(5) Uani 1 1 d . . . . .
C15 C 0.5648(3) 0.5680(2) 0.2505(3) 0.0202(5) Uani 1 1 d . . . . .
C16 C 0.7127(3) 0.6019(2) 0.2911(3) 0.0263(6) Uani 1 1 d . . . . .
H16 H 0.736195 0.639942 0.378257 0.032 Uiso 1 1 calc R . . . .
C17 C 0.8260(3) 0.5806(2) 0.2055(4) 0.0353(7) Uani 1 1 d . . . . .
H17 H 0.926507 0.602941 0.235477 0.042 Uiso 1 1 calc R . . . .
C18 C 0.7924(3) 0.5270(2) 0.0767(4) 0.0364(8) Uani 1 1 d . . . . .
H18 H 0.870385 0.510785 0.019815 0.044 Uiso 1 1 calc R . . . .
C19 C 0.6459(3) 0.4972(2) 0.0315(3) 0.0306(7) Uani 1 1 d . . . . .
H19 H 0.622035 0.462485 -0.058415 0.037 Uiso 1 1 calc R . . . .
C20 C 0.5326(3) 0.5179(2) 0.1175(3) 0.0239(6) Uani 1 1 d . . . . .
H20 H 0.431634 0.497556 0.085017 0.029 Uiso 1 1 calc R . . . .
C21 C 0.2946(3) 0.6171(2) 0.2760(3) 0.0185(5) Uani 1 1 d . . . . .
H21a H 0.256234 0.566175 0.201154 0.022 Uiso 1 1 calc R . . . .
H21b H 0.220760 0.621330 0.346709 0.022 Uiso 1 1 calc R . . . .
C22 C 0.3051(3) 0.7222(2) 0.2035(3) 0.0237(6) Uani 1 1 d . . . . .
H22a H 0.333653 0.774634 0.278962 0.028 Uiso 1 1 calc R . . . .
H22b H 0.385178 0.720037 0.139008 0.028 Uiso 1 1 calc R . . . .
C23 C 0.1563(3) 0.7523(2) 0.1156(3) 0.0283(6) Uani 1 1 d . . . . .
H23a H 0.077987 0.758217 0.180066 0.042 Uiso 1 1 calc GR . . . .
H23b H 0.126770 0.699888 0.041897 0.042 Uiso 1 1 calc GR . . . .
H23c H 0.168130 0.818425 0.068083 0.042 Uiso 1 1 calc GR . . . .
C24 C 0.3554(3) 0.4875(2) 0.5785(2) 0.0167(5) Uani 1 1 d . . . . .
C25 C 0.3385(3) 0.3982(2) 0.6599(3) 0.0203(5) Uani 1 1 d . . . . .
H25 H 0.374378 0.334675 0.627712 0.024 Uiso 1 1 calc R . . . .
C26 C 0.2709(3) 0.4009(2) 0.7860(3) 0.0224(6) Uani 1 1 d . . . . .
H26 H 0.260783 0.340402 0.840945 0.027 Uiso 1 1 calc R . . . .
C27 C 0.2189(3) 0.4937(2) 0.8289(2) 0.0223(6) Uani 1 1 d . . . . .
C28 C 0.2358(3) 0.5830(2) 0.7562(3) 0.0251(6) Uani 1 1 d . . . . .
H28 H 0.201233 0.646325 0.790273 0.030 Uiso 1 1 calc R . . . .
C29 C 0.3058(3) 0.5786(2) 0.6295(3) 0.0209(5) Uani 1 1 d . . . . .
H29 H 0.319329 0.640095 0.577916 0.025 Uiso 1 1 calc R . . . .


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 C27 1.366(3) . ?
O1 C8 1.381(3) . ?
O1 C9 1.382(3) . ?
C1 C2 1.593(3) . ?
C1 C15 1.524(3) . ?
C1 C21 1.536(3) . ?
C2 C3 1.528(3) . ?
C2 C14 1.526(3) . ?
C2 C24 1.542(3) . ?
C3 C4 1.398(3) . ?
C3 C8 1.383(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.389(4) . ?
C6 C7 1.384(4) . ?
C7 C8 1.388(4) . ?
C9 C10 1.386(4) . ?
C9 C14 1.391(3) . ?
C10 C11 1.385(4) . ?
C11 C12 1.385(4) . ?
C12 C13 1.382(4) . ?
C13 C14 1.396(3) . ?
C15 C16 1.397(4) . ?
C15 C20 1.396(4) . ?
C16 C17 1.392(4) . ?
C17 C18 1.386(5) . ?
C18 C19 1.377(4) . ?
C19 C20 1.393(4) . ?
C21 C22 1.535(4) . ?
C22 C23 1.518(4) . ?
C24 C25 1.407(4) . ?
C24 C29 1.374(4) . ?
C25 C26 1.386(4) . ?
C26 C27 1.374(4) . ?
C27 C28 1.365(4) . ?
C28 C29 1.402(4) . ?

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
C8 O1 C9 117.99(19) . . ?
C15 C1 C2 109.2(2) . . ?
C15 C1 C21 111.8(2) . . ?
C21 C1 C2 114.66(19) . . ?
C3 C2 C1 106.79(19) . . ?
C3 C2 C24 107.44(18) . . ?
C14 C2 C1 110.41(18) . . ?
C14 C2 C3 109.0(2) . . ?
C14 C2 C24 109.42(19) . . ?
C24 C2 C1 113.7(2) . . ?
C4 C3 C2 120.7(2) . . ?
C8 C3 C2 121.2(2) . . ?
C8 C3 C4 117.8(2) . . ?
C5 C4 C3 121.1(2) . . ?
C4 C5 C6 119.7(2) . . ?
C7 C6 C5 120.2(2) . . ?
C6 C7 C8 119.2(2) . . ?
O1 C8 C3 123.0(2) . . ?
O1 C8 C7 115.1(2) . . ?
C3 C8 C7 121.9(2) . . ?
O1 C9 C10 115.3(2) . . ?
O1 C9 C14 122.6(2) . . ?
C10 C9 C14 122.1(2) . . ?
C11 C10 C9 119.3(2) . . ?
C10 C11 C12 120.0(2) . . ?
C13 C12 C11 119.8(2) . . ?
C12 C13 C14 121.6(2) . . ?
C9 C14 C2 121.3(2) . . ?
C9 C14 C13 117.2(2) . . ?
C13 C14 C2 121.4(2) . . ?
C16 C15 C1 120.1(2) . . ?
C20 C15 C1 121.8(2) . . ?
C20 C15 C16 117.9(2) . . ?
C17 C16 C15 120.8(3) . . ?
C18 C17 C16 120.2(3) . . ?
C19 C18 C17 119.9(3) . . ?
C18 C19 C20 120.0(3) . . ?
C19 C20 C15 121.2(3) . . ?
C22 C21 C1 113.1(2) . . ?
C23 C22 C21 111.7(2) . . ?
C25 C24 C2 116.9(2) . . ?
C29 C24 C2 125.0(2) . . ?
C29 C24 C25 117.9(2) . . ?
C26 C25 C24 121.5(2) . . ?
C27 C26 C25 117.9(2) . . ?
F1 C27 C26 118.6(2) . . ?
C28 C27 F1 118.4(2) . . ?
C28 C27 C26 123.0(2) . . ?
C27 C28 C29 118.1(2) . . ?
C24 C29 C28 121.5(2) . . ?
