# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_od3_auto
_database_code_depnum_ccdc_archive 'CCDC 2211859'
loop_
_audit_author_name
_audit_author_address
'Lingsong Wang'
;Tianjin University
China
;
_audit_update_record             
;
2022-10-09 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2022-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        OFN-DMA
_chemical_formula_moiety         '0.07(C10 F8), 0.07(C16 H14)'
_chemical_formula_sum            'C1.86 H F0.57'
_chemical_formula_weight         34.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHF
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8480(4)
_cell_length_b                   8.8391(6)
_cell_length_c                   9.0199(7)
_cell_angle_alpha                100.682(6)
_cell_angle_beta                 102.679(6)
_cell_angle_gamma                104.957(6)
_cell_volume                     497.36(6)
_cell_formula_units_Z            14
_cell_measurement_reflns_used    2380
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.5170
_cell_measurement_theta_min      4.2830
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             242
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5521
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.484
_diffrn_reflns_theta_min         3.209
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  75.00   1.00   40.00    --   10.51-149.00 -85.00   27
  2  ω     28.00  63.00   1.00   40.00    --   10.51-123.00  78.00   35
  3  ω    -59.00  -9.00   1.00   40.00    --   10.51 -57.00 150.00   50
  4  ω     -5.00  39.00   1.00   40.00    --   10.51 -57.00 150.00   44
  5  ω    -36.00  20.00   1.00   40.00    --  -10.82  77.00  30.00   56
  6  ω    -43.00 -12.00   1.00   40.00    --  -10.82  77.00 -60.00   31
  7  ω    -40.00  22.00   1.00   40.00    --  -10.82 -77.00  90.00   62
  8  ω    -37.00  62.00   1.00   40.00    --  -10.82  57.00 -90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0415818000
_diffrn_orient_matrix_UB_12      0.0835315000
_diffrn_orient_matrix_UB_13      0.0396830000
_diffrn_orient_matrix_UB_21      -0.0237261000
_diffrn_orient_matrix_UB_22      0.0202091000
_diffrn_orient_matrix_UB_23      -0.0729678000
_diffrn_orient_matrix_UB_31      -0.1009553000
_diffrn_orient_matrix_UB_32      0.0000134000
_diffrn_orient_matrix_UB_33      0.0075025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          NONE
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1657
_reflns_number_total             2370
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0709
_refine_ls_restrained_S_all      1.050
_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)+(0.1075P)²+0.1241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2153
_refine_special_details          NONE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00D(H00D), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00G(H00B,H00C,H00E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F001 F 0.0871(3) 0.34092(17) -0.0308(2) 0.1005(6) Uani 1 1 d . . . . .
F002 F 0.1991(2) 0.1952(3) 0.44186(15) 0.1078(7) Uani 1 1 d . . . . .
F003 F 0.2140(2) 0.42185(17) 0.2826(2) 0.1070(7) Uani 1 1 d . . . . .
F004 F 0.0611(3) -0.1180(2) 0.29209(19) 0.1015(6) Uani 1 1 d . . . . .
C005 C 0.4266(2) 0.83263(19) 0.9273(2) 0.0429(4) Uani 1 1 d . . . . .
C006 C 0.5047(3) 1.1151(2) 0.9076(2) 0.0450(4) Uani 1 1 d . . . . .
C007 C 0.0037(2) 0.0603(2) -0.0422(2) 0.0443(4) Uani 1 1 d . . . . .
C008 C 0.4310(2) 0.9481(2) 0.83471(19) 0.0424(4) Uani 1 1 d . . . . .
C009 C 0.3499(3) 0.6646(2) 0.8460(3) 0.0598(5) Uani 1 1 d . . . . .
H009 H 0.3455 0.5876 0.9039 0.072 Uiso 1 1 calc R . . . .
C00A C 0.3571(3) 0.8869(3) 0.6668(2) 0.0587(5) Uani 1 1 d . . . . .
H00A H 0.3581 0.9599 0.6045 0.070 Uiso 1 1 calc R . . . .
C00B C 0.0786(3) 0.2236(2) 0.0446(3) 0.0592(5) Uani 1 1 d . . . . .
C00C C 0.0646(3) -0.0091(3) 0.2078(2) 0.0591(5) Uani 1 1 d . . . . .
C00D C 0.2866(4) 0.7271(3) 0.5968(3) 0.0699(6) Uani 1 1 d . . . . .
H00D H 0.2396 0.6915 0.4877 0.084 Uiso 1 1 calc R . . . .
C00E C 0.1425(3) 0.2659(3) 0.2031(3) 0.0659(6) Uani 1 1 d . . . . .
C00F C 0.2833(3) 0.6144(3) 0.6868(3) 0.0710(7) Uani 1 1 d . . . . .
H00F H 0.2353 0.5042 0.6373 0.085 Uiso 1 1 calc R . . . .
C00G C 0.5114(4) 1.2374(3) 0.8107(3) 0.0755(7) Uani 1 1 d . . . . .
H00B H 0.3930 1.2769 0.8087 0.113 Uiso 1 1 calc GR . . . .
H00C H 0.5058 1.1870 0.7053 0.113 Uiso 1 1 calc GR . . . .
H00E H 0.6395 1.3262 0.8563 0.113 Uiso 1 1 calc GR . . . .
C00H C 0.1353(3) 0.1496(3) 0.2848(2) 0.0659(6) 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
F001 C00B 1.337(3) . ?
F002 C00H 1.337(2) . ?
F003 C00E 1.336(2) . ?
F004 C00C 1.331(3) . ?
C005 C006 1.407(2) 2_677 ?
C005 C008 1.432(3) . ?
C005 C009 1.429(2) . ?
C006 C005 1.407(2) 2_677 ?
C006 C008 1.405(2) . ?
C006 C00G 1.510(3) . ?
C007 C007 1.416(4) 2 ?
C007 C00B 1.408(3) . ?
C007 C00C 1.410(3) 2 ?
C008 C00A 1.436(2) . ?
C009 H009 0.9300 . ?
C009 C00F 1.356(3) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.346(3) . ?
C00B C00E 1.348(3) . ?
C00C C007 1.410(3) 2 ?
C00C C00H 1.352(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.396(4) . ?
C00E C00H 1.368(4) . ?
C00F H00F 0.9300 . ?
C00G H00B 0.9600 . ?
C00G H00C 0.9600 . ?
C00G H00E 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
C006 C005 C008 120.38(16) 2_677 . ?
C006 C005 C009 121.91(18) 2_677 . ?
C009 C005 C008 117.72(17) . . ?
C005 C006 C00G 120.13(17) 2_677 . ?
C008 C006 C005 119.16(16) . 2_677 ?
C008 C006 C00G 120.71(17) . . ?
C00B C007 C007 117.9(2) . 2 ?
C00B C007 C00C 124.1(2) . 2 ?
C00C C007 C007 117.9(2) 2 2 ?
C005 C008 C00A 117.66(17) . . ?
C006 C008 C005 120.46(16) . . ?
C006 C008 C00A 121.87(18) . . ?
C005 C009 H009 119.1 . . ?
C00F C009 C005 121.8(2) . . ?
C00F C009 H009 119.1 . . ?
C008 C00A H00A 119.0 . . ?
C00D C00A C008 121.9(2) . . ?
C00D C00A H00A 119.0 . . ?
F001 C00B C007 119.7(2) . . ?
F001 C00B C00E 118.6(2) . . ?
C00E C00B C007 121.7(2) . . ?
F004 C00C C007 120.1(2) . 2 ?
F004 C00C C00H 118.4(2) . . ?
C00H C00C C007 121.5(2) . 2 ?
C00A C00D H00D 119.8 . . ?
C00A C00D C00F 120.5(2) . . ?
C00F C00D H00D 119.8 . . ?
F003 C00E C00B 120.5(2) . . ?
F003 C00E C00H 119.1(2) . . ?
C00B C00E C00H 120.45(19) . . ?
C009 C00F C00D 120.39(19) . . ?
C009 C00F H00F 119.8 . . ?
C00D C00F H00F 119.8 . . ?
C006 C00G H00B 109.5 . . ?
C006 C00G H00C 109.5 . . ?
C006 C00G H00E 109.5 . . ?
H00B C00G H00C 109.5 . . ?
H00B C00G H00E 109.5 . . ?
H00C C00G H00E 109.5 . . ?
F002 C00H C00C 120.4(3) . . ?
F002 C00H C00E 119.1(2) . . ?
C00C C00H C00E 120.49(19) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.735
