# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Tweig_ZL05014_0m
_database_code_depnum_ccdc_archive 'CCDC 1456337'
loop_
_audit_author_name
_audit_author_address
'Scott Daniel Bunge'
;Kent State University
United States of America
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2021-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            1,4-difluoro-2,3-dimethoxytriphenylene
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 F2 O2'
_chemical_formula_sum            'C20 H14 F2 O2'
_chemical_formula_weight         324.31

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                   9.680(3)
_cell_length_b                   3.9219(10)
_cell_length_c                   37.508(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.613(8)
_cell_angle_gamma                90
_cell_volume                     1423.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    760
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      22.60

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   sadabs

_exptl_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            5570
_diffrn_reflns_av_unetI/netI     0.1364
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         1.086
_diffrn_reflns_theta_max         25.723
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.921
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.921
_reflns_number_total             2451
_reflns_number_gt                1220
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1000P)²+0.4371P] 
 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         2451
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1540
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2046
_refine_ls_wR_factor_gt          0.1491
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_restrained_S_all      0.904
_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 0.9524(2) -0.1513(7) 0.12732(7) 0.0299(7) Uani 1 1 d . . . . .
F2 F 0.4407(2) -0.1669(7) 0.06578(7) 0.0305(8) Uani 1 1 d . . . . .
O1 O 0.9128(3) -0.4242(8) 0.06280(9) 0.0308(9) Uani 1 1 d . . . . .
O2 O 0.6469(3) -0.4376(8) 0.03195(8) 0.0320(9) Uani 1 1 d . . . . .
C1 C 0.3709(4) 0.4499(11) 0.18715(12) 0.0199(11) Uani 1 1 d . . . . .
H1 H 0.3833 0.5260 0.2111 0.024 Uiso 1 1 calc R U . . .
C2 C 0.2429(5) 0.4815(12) 0.17061(13) 0.0240(12) Uani 1 1 d . . . . .
H2 H 0.1684 0.5792 0.1830 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2229(5) 0.3705(11) 0.13576(13) 0.0253(12) Uani 1 1 d . . . . .
H3 H 0.1350 0.3950 0.1241 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3313(4) 0.2239(12) 0.11794(12) 0.0226(11) Uani 1 1 d . . . . .
H4 H 0.3163 0.1489 0.0941 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4640(4) 0.1826(11) 0.13431(11) 0.0179(11) Uani 1 1 d . . . . .
C6 C 0.5813(4) 0.0257(11) 0.11576(11) 0.0167(11) Uani 1 1 d . . . . .
C7 C 0.5670(4) -0.1338(11) 0.08255(12) 0.0196(11) Uani 1 1 d . . . . .
C8 C 0.6740(5) -0.2735(11) 0.06378(12) 0.0212(11) Uani 1 1 d . . . . .
C9 C 0.8052(5) -0.2643(11) 0.07985(13) 0.0231(11) Uani 1 1 d . . . . .
C10 C 0.8221(4) -0.1233(12) 0.11316(12) 0.0212(11) Uani 1 1 d . . . . .
C11 C 0.7151(4) 0.0286(11) 0.13225(11) 0.0167(11) Uani 1 1 d . . . . .
C12 C 0.7376(4) 0.1811(11) 0.16802(11) 0.0172(11) Uani 1 1 d . . . . .
C13 C 0.8707(4) 0.2176(11) 0.18486(12) 0.0217(11) Uani 1 1 d . . . . .
H13 H 0.9499 0.1489 0.1723 0.026 Uiso 1 1 calc R U . . .
C14 C 0.8882(5) 0.3476(12) 0.21839(12) 0.0244(12) Uani 1 1 d . . . . .
H14 H 0.9784 0.3678 0.2288 0.029 Uiso 1 1 calc R U . . .
C15 C 0.7739(5) 0.4509(12) 0.23745(12) 0.0231(11) Uani 1 1 d . . . . .
H15 H 0.7851 0.5349 0.2611 0.028 Uiso 1 1 calc R U . . .
C16 C 0.6454(4) 0.4293(12) 0.22153(11) 0.0195(11) Uani 1 1 d . . . . .
H16 H 0.5682 0.5048 0.2345 0.023 Uiso 1 1 calc R U . . .
C17 C 0.6221(4) 0.3001(11) 0.18672(11) 0.0160(10) Uani 1 1 d . . . . .
C18 C 0.4843(4) 0.3076(11) 0.16958(11) 0.0164(11) Uani 1 1 d . . . . .
C19 C 1.0249(5) -0.2061(12) 0.05268(13) 0.0345(14) Uani 1 1 d . . . . .
H19A H 0.9875 -0.0016 0.0409 0.052 Uiso 1 1 calc R U . . .
H19B H 1.0843 -0.3287 0.0363 0.052 Uiso 1 1 calc R U . . .
H19C H 1.0792 -0.1396 0.0740 0.052 Uiso 1 1 calc R U . . .
C20 C 0.6776(6) -0.2469(13) 0.00119(13) 0.0405(15) Uani 1 1 d . . . . .
H20A H 0.6353 -0.0206 0.0027 0.061 Uiso 1 1 calc R U . . .
H20B H 0.6409 -0.3652 -0.0201 0.061 Uiso 1 1 calc R U . . .
H20C H 0.7780 -0.2228 -0.0004 0.061 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 C10 1.359(5) . ?
F2 C7 1.365(5) . ?
O1 C9 1.387(5) . ?
O1 C19 1.441(5) . ?
O2 C8 1.375(5) . ?
O2 C20 1.414(5) . ?
C1 C2 1.376(6) . ?
C1 C18 1.412(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(6) . ?
C4 H4 0.9500 . ?
C5 C18 1.420(6) . ?
C5 C6 1.482(6) . ?
C6 C7 1.397(6) . ?
C6 C11 1.419(6) . ?
C7 C8 1.382(6) . ?
C8 C9 1.390(6) . ?
C9 C10 1.372(6) . ?
C10 C11 1.408(6) . ?
C11 C12 1.480(6) . ?
C12 C17 1.416(6) . ?
C12 C13 1.426(6) . ?
C13 C14 1.363(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.367(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.413(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.464(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C9 O1 C19 115.7(3) . . ?
C8 O2 C20 114.9(4) . . ?
C2 C1 C18 121.9(4) . . ?
C2 C1 H1 119.1 . . ?
C18 C1 H1 119.1 . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.9(4) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C18 117.7(4) . . ?
C4 C5 C6 122.8(4) . . ?
C18 C5 C6 119.5(4) . . ?
C7 C6 C11 117.3(4) . . ?
C7 C6 C5 123.1(4) . . ?
C11 C6 C5 119.6(4) . . ?
F2 C7 C8 113.7(4) . . ?
F2 C7 C6 121.2(4) . . ?
C8 C7 C6 125.1(4) . . ?
O2 C8 C7 120.0(4) . . ?
O2 C8 C9 122.6(4) . . ?
C7 C8 C9 117.2(4) . . ?
C10 C9 O1 122.0(4) . . ?
C10 C9 C8 119.3(4) . . ?
O1 C9 C8 118.5(4) . . ?
F1 C10 C9 114.2(4) . . ?
F1 C10 C11 121.5(4) . . ?
C9 C10 C11 124.3(4) . . ?
C10 C11 C6 116.8(4) . . ?
C10 C11 C12 122.7(4) . . ?
C6 C11 C12 120.5(4) . . ?
C17 C12 C13 117.6(4) . . ?
C17 C12 C11 119.0(4) . . ?
C13 C12 C11 123.4(4) . . ?
C14 C13 C12 122.2(4) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 120.1(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 118.9(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 123.1(4) . . ?
C15 C16 H16 118.5 . . ?
C17 C16 H16 118.5 . . ?
C16 C17 C12 117.9(4) . . ?
C16 C17 C18 121.2(4) . . ?
C12 C17 C18 120.7(4) . . ?
C1 C18 C5 118.8(4) . . ?
C1 C18 C17 120.9(4) . . ?
C5 C18 C17 120.2(4) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-2

# start Validation Reply Form
_vrf_PLAT029_Tweig_ZL05014_0m    
;
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.921 Note
RESPONSE:  Reflections are missing from the high angle data
because they are too weak to be counted.
;
# end Validation Reply Form 
