# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2151352'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2022-02-10 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 F6 O'
_chemical_formula_weight         310.24

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.8199(8)
_cell_length_b                   11.7062(14)
_cell_length_c                   18.082(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1231.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3723
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5657
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11485
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.072
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_full        25.034
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2168
_reflns_number_gt                1789
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.1042P)²+3.5614P] 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_abs_structure_details 
; 
 Flack x determined using 596 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.5(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2168
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2160
_refine_ls_wR_factor_gt          0.2021
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.5547(15) 0.5897(7) 0.5605(5) 0.036(2) Uani 1 1 d . . . . .
C2 C 0.7663(17) 0.6288(7) 0.5500(5) 0.036(2) Uani 1 1 d . . . . .
C3 C 0.5851(14) 0.5724(7) 0.6415(5) 0.0323(19) Uani 1 1 d . . . . .
C4 C 0.8392(15) 0.6198(6) 0.6280(5) 0.0348(19) Uani 1 1 d . . . . .
C5 C 0.5355(13) 0.6750(6) 0.6910(4) 0.0290(17) Uani 1 1 d . . . . .
C6 C 0.7849(13) 0.7197(6) 0.6772(5) 0.0289(17) Uani 1 1 d . . . . .
C7 C 0.8367(14) 0.6999(7) 0.7614(5) 0.0334(18) Uani 1 1 d . . . . .
H7 H 0.938785 0.632090 0.768483 0.040 Uiso 1 1 calc R U . . .
C8 C 0.9271(16) 0.8023(7) 0.8038(5) 0.0371(19) Uani 1 1 d . . . . .
H8A H 0.847722 0.872208 0.786612 0.045 Uiso 1 1 calc R U . . .
H8B H 1.093343 0.811415 0.793893 0.045 Uiso 1 1 calc R U . . .
C9 C 0.887(3) 0.7869(10) 0.8911(7) 0.088(5) Uani 1 1 d . . . . .
H9A H 0.973725 0.846959 0.917521 0.106 Uiso 1 1 calc R U . . .
H9B H 0.721604 0.798621 0.901867 0.106 Uiso 1 1 calc R U . . .
C10 C 0.9529(19) 0.6801(10) 0.9187(6) 0.056(3) Uani 1 1 d . . . . .
H10 H 1.118954 0.661099 0.911598 0.067 Uiso 1 1 calc R U . . .
C11 C 0.793(2) 0.5773(11) 0.9203(7) 0.071(4) Uani 1 1 d . . . . .
H11 H 0.867694 0.500826 0.915294 0.085 Uiso 1 1 calc R U . . .
C12 C 0.556(2) 0.5819(11) 0.9030(6) 0.071(4) Uani 1 1 d . . . . .
H12A H 0.493388 0.657358 0.917382 0.086 Uiso 1 1 calc R U . . .
H12B H 0.472864 0.522642 0.931564 0.086 Uiso 1 1 calc R U . . .
C13 C 0.5154(17) 0.5624(7) 0.8195(5) 0.040(2) Uani 1 1 d . . . . .
H13A H 0.607982 0.496317 0.802774 0.048 Uiso 1 1 calc R U . . .
H13B H 0.351443 0.544176 0.810929 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5809(13) 0.6676(7) 0.7742(4) 0.0299(18) Uani 1 1 d . . . . .
H14 H 0.504583 0.734909 0.797746 0.036 Uiso 1 1 calc R U . . .
F1 F 0.3671(8) 0.5837(4) 0.5207(3) 0.0391(12) Uani 1 1 d . . . . .
F2 F 0.8656(9) 0.6809(4) 0.4929(3) 0.0441(13) Uani 1 1 d . . . . .
F3 F 0.5552(8) 0.4647(3) 0.6694(3) 0.0365(12) Uani 1 1 d . . . . .
F4 F 1.0252(8) 0.5551(4) 0.6444(3) 0.0388(12) Uani 1 1 d . . . . .
F5 F 0.3428(8) 0.7364(3) 0.6700(2) 0.0326(11) Uani 1 1 d . . . . .
F6 F 0.8343(8) 0.8269(3) 0.6508(2) 0.0315(11) Uani 1 1 d . . . . .
O1 O 0.8604(13) 0.6475(7) 0.9892(3) 0.061(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 F1 1.310(10) . ?
C1 C2 1.328(13) . ?
C1 C3 1.488(12) . ?
C2 F2 1.330(9) . ?
C2 C4 1.477(12) . ?
C3 F3 1.370(9) . ?
C3 C5 1.526(11) . ?
C3 C4 1.598(11) . ?
C4 F4 1.354(10) . ?
C4 C6 1.504(11) . ?
C5 F5 1.385(9) . ?
C5 C14 1.530(11) . ?
C5 C6 1.563(10) . ?
C6 F6 1.373(8) . ?
C6 C7 1.569(12) . ?
C7 C8 1.517(11) . ?
C7 C14 1.554(11) . ?
C8 C9 1.606(16) . ?
C9 C10 1.401(15) . ?
C10 O1 1.434(12) . ?
C10 C11 1.523(18) . ?
C11 C12 1.416(18) . ?
C11 O1 1.543(16) . ?
C12 C13 1.545(14) . ?
C13 C14 1.526(11) . ?

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
F1 C1 C2 135.4(8) . . ?
F1 C1 C3 129.2(8) . . ?
C2 C1 C3 94.5(8) . . ?
C1 C2 F2 132.3(9) . . ?
C1 C2 C4 96.0(7) . . ?
F2 C2 C4 130.5(8) . . ?
F3 C3 C1 118.2(7) . . ?
F3 C3 C5 119.0(7) . . ?
C1 C3 C5 116.6(7) . . ?
F3 C3 C4 119.5(6) . . ?
C1 C3 C4 85.0(6) . . ?
C5 C3 C4 89.5(6) . . ?
F4 C4 C2 118.7(7) . . ?
F4 C4 C6 118.2(7) . . ?
C2 C4 C6 116.7(7) . . ?
F4 C4 C3 120.8(6) . . ?
C2 C4 C3 84.6(6) . . ?
C6 C4 C3 89.1(6) . . ?
F5 C5 C3 113.6(6) . . ?
F5 C5 C14 116.1(7) . . ?
C3 C5 C14 120.0(6) . . ?
F5 C5 C6 122.3(6) . . ?
C3 C5 C6 89.7(6) . . ?
C14 C5 C6 90.9(6) . . ?
F6 C6 C4 117.4(6) . . ?
F6 C6 C5 123.8(6) . . ?
C4 C6 C5 91.7(6) . . ?
F6 C6 C7 115.6(6) . . ?
C4 C6 C7 114.8(6) . . ?
C5 C6 C7 88.5(6) . . ?
C8 C7 C14 116.7(7) . . ?
C8 C7 C6 116.2(6) . . ?
C14 C7 C6 89.8(6) . . ?
C7 C8 C9 111.0(7) . . ?
C10 C9 C8 114.3(11) . . ?
C9 C10 O1 116.9(11) . . ?
C9 C10 C11 122.9(11) . . ?
O1 C10 C11 62.8(7) . . ?
C12 C11 C10 124.2(11) . . ?
C12 C11 O1 114.0(11) . . ?
C10 C11 O1 55.8(7) . . ?
C11 C12 C13 111.0(11) . . ?
C14 C13 C12 111.5(8) . . ?
C13 C14 C5 122.0(7) . . ?
C13 C14 C7 121.1(7) . . ?
C5 C14 C7 90.3(6) . . ?
C10 O1 C11 61.4(6) . . ?

_refine_diff_density_max         0.964
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.094



# start Validation Reply Form
_vrf_PLAT097_4                   
;
PROBLEM: Large Reported Max. (Positive) Residual Density 0.96 eA-3
RESPONSE: The compound exhibited some positional disorder about the epoxide 
functional group.  Modeling multiple positions did not improve the 
refinement. This disorder did result in larger residual electron density 
and greater error in C-C and C-O bonds. However, composition
and connectivity are unambiguous.
;
_vrf_PLAT230_4                   
;
PROBLEM: Hirshfeld Test Diff for O1 --C11 . 9.7 s.u.
RESPONSE: The compound exhibited some positional disorder about the epoxide 
functional group.  Modeling multiple positions did not improve the 
refinement. This disorder did result in larger residual electron density 
and greater error in C-C and C-O bonds. However, composition
and connectivity are unambiguous.
;

_vrf_PLAT340_4                   
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01306 Ang.
RESPONSE: The compound exhibited some positional disorder about the epoxide 
functional group.  Modeling multiple positions did not improve the 
refinement. This disorder did result in larger residual electron density 
and greater error in C-C and C-O bonds. However, composition
and connectivity are unambiguous.
;
# end Validation Reply Form

