# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_jx4_2_292_b_auto
_database_code_depnum_ccdc_archive 'CCDC 2390297'
loop_
_audit_author_name
_audit_author_address
'Chris Ritchie'
;Monash University
Australia
;
_audit_update_record             
;
2024-10-11 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_audit_creation_date             2024-07-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
2-(4-(diphenylamino)-2-methylpyridin-1-ium-1-yl)-4,4,5,5-tetrafluoro-3-oxocyclopent-1-en-1-olate
_chemical_formula_moiety         'C23 H16 F4 N2 O2, 1.5[H2O]'
_chemical_formula_sum            'C23 H19 F4 N2 O3.50'
_chemical_formula_weight         455.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H16F4N2O2
_chemical_oxdiff_usercomment     'Colourless block at 292.5 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.4180(5)
_cell_length_b                   10.7857(2)
_cell_length_c                   18.1600(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.368(3)
_cell_angle_gamma                90
_cell_volume                     4327.26(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8293
_cell_measurement_temperature    292.47(10)
_cell_measurement_theta_max      79.4020
_cell_measurement_theta_min      3.9510
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.537
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (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    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1880
_exptl_crystal_preparation       oil
_exptl_crystal_recrystallization_method acetone
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.219
_diffrn_reflns_theta_min         4.002
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.47(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 -48.00   0.50    0.78    --  -91.75 125.00  60.00   52
  2  ω    -68.00 -43.00   0.50    0.78    --  -91.75  24.00   3.00   50
  3  ω   -121.00 -35.00   0.50    0.20    --  -47.91 -24.00-161.00  172
  4  ω    -51.00  21.00   0.50    0.20    --  -47.91  24.00   3.00  144
  5  ω   -146.00-121.00   0.50    0.78    --  -91.75 -24.00-161.00   50
  6  ω     48.00 104.00   0.50    0.78    --  113.25 -94.00 150.00  112
  7  ω     73.00  99.00   0.50    0.78    --  113.25 -94.00  90.00   52
  8  ω     46.00 134.00   0.50    0.78    --  113.25 -77.00 -60.00  176
  9  ω     63.00 111.00   0.50    0.78    --  113.25 -61.00  30.00   96
 10  ω     47.00  73.00   0.50    0.78    --  113.25 -45.00 -30.00   52
 11  ω     44.00  76.00   0.50    0.78    --  113.25 -45.00   0.00   64
 12  ω     49.00  76.00   0.50    0.78    --  113.25 -45.00  30.00   54
 13  ω     45.00  76.00   0.50    0.78    --  113.25 -45.00  60.00   62
 14  ω     42.00  68.00   0.50    0.78    --  113.25 -45.00 120.00   52
 15  ω     40.00  65.00   0.50    0.78    --  113.25 -30.00 150.00   50
 16  ω     39.00  65.00   0.50    0.78    --  113.25 -30.00  60.00   52
 17  ω     39.00  65.00   0.50    0.78    --  113.25 -30.00  30.00   52
 18  ω     41.00  66.00   0.50    0.78    --  113.25 -30.00   0.00   50
 19  ω     39.00  65.00   0.50    0.78    --  113.25 -30.00-120.00   52
 20  ω     39.00  65.00   0.50    0.78    --  113.25 -30.00-180.00   52
 21  ω     40.00  69.00   0.50    0.78    --  113.25 -24.00-161.00   58
 22  ω     44.00  70.00   0.50    0.78    --  113.25 -45.00-120.00   52
 23  ω    112.00 161.00   0.50    0.78    --  113.25  30.00-120.00   98
 24  ω    103.00 178.00   0.50    0.78    --  113.25  24.00   3.00  150
 25  ω    119.00 170.00   0.50    0.78    --  113.25  15.00 -30.00  102
 26  ω     79.00 117.00   0.50    0.20    --   47.91  24.00   3.00   76
 27  ω     44.00  70.00   0.50    0.20    --   47.91  24.00   3.00   52
 28  ω     -7.00  18.00   0.50    0.20    --   47.91 -24.00-161.00   50
 29  ω    -20.00  59.00   0.50    0.20    --   47.91 -37.00  90.00  158
 30  ω    153.00 178.00   0.50    0.78    --  113.25 125.00-150.00   50
 31  ω    103.00 129.00   0.50    0.78    --  113.25 125.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0605725000
_diffrn_orient_matrix_UB_12      0.0083915000
_diffrn_orient_matrix_UB_13      -0.0157885000
_diffrn_orient_matrix_UB_21      0.0337710000
_diffrn_orient_matrix_UB_22      -0.0436480000
_diffrn_orient_matrix_UB_23      0.0839850000
_diffrn_orient_matrix_UB_31      -0.0070933000
_diffrn_orient_matrix_UB_32      -0.1357736000
_diffrn_orient_matrix_UB_33      -0.0279907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3749
_reflns_number_total             4603
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4603
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.058
_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)+(0.0688P)²+1.5302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1379
_refine_special_details          ?
_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. Restrained distances
 F2-C21 \\sim F2A-C21A
 with sigma of 0.02
 C20-C21 \\sim C20-C21A
 with sigma of 0.02
 F1-C21 \\sim F1A-C21A
 with sigma of 0.02
 F4-C22 \\sim F4A-C22A
 with sigma of 0.02
 F3-C22 \\sim F3A-C22A
 with sigma of 0.02
 C23-C22 \\sim C23-C22A
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 F2-C20 \\sim F2A-C20
 with sigma of 0.04
 F2-F1 \\sim F2A-F1A
 with sigma of 0.04
 F2-C22 \\sim F2A-C22A
 with sigma of 0.04
 C20-F1 \\sim C20-F1A
 with sigma of 0.04
 C20-C22 \\sim C20-C22A
 with sigma of 0.04
 F1-C22 \\sim F1A-C22A
 with sigma of 0.04
 F4-F3 \\sim F4A-F3A
 with sigma of 0.04
 F4-C23 \\sim F4A-C23
 with sigma of 0.04
 F4-C21 \\sim F4A-C21A
 with sigma of 0.04
 F3-C23 \\sim F3A-C23
 with sigma of 0.04
 F3-C21 \\sim F3A-C21A
 with sigma of 0.04
 C23-C21 \\sim C23-C21A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F2, F1, F4, F3, C21, C22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2A, F1A, F4A, F3A, C21A, C22A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C21A)=Sof(F2A)=Sof(C22A)=Sof(F1A)=Sof(F4A)=Sof(F3A)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F4)=Sof(F3)=Sof(C21)=Sof(C22)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C15(H15), C3(H3), C5(H5), C11(H11), C1(H1), C6(H6),
 C9(H9), C2(H2), C12(H12), C7(H7), C8(H8)
5.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
N2 N 0.59723(5) 0.65608(10) 0.54802(6) 0.0401(3) Uani 1 1 d . . . . .
O1 O 0.59694(6) 0.82662(13) 0.41956(8) 0.0681(3) Uani 1 1 d . . . . .
N1 N 0.74171(5) 0.45347(11) 0.68972(7) 0.0448(3) Uani 1 1 d . . . . .
O2 O 0.46543(6) 0.62958(15) 0.53176(9) 0.0755(4) Uani 1 1 d . . . . .
F2 F 0.4724(4) 0.8093(12) 0.3150(4) 0.107(2) Uani 0.574(19) 1 d D . P A 1
C13 C 0.69509(6) 0.52194(12) 0.64331(8) 0.0395(3) Uani 1 1 d . . . . .
C17 C 0.65996(6) 0.59833(13) 0.67424(8) 0.0421(3) Uani 1 1 d . . . . .
H17 H 0.669371 0.603067 0.728099 0.051 Uiso 1 1 calc R U . . .
C4 C 0.74912(6) 0.42746(12) 0.77027(8) 0.0412(3) Uani 1 1 d . . . . .
C14 C 0.68009(7) 0.52113(13) 0.56150(8) 0.0443(3) Uani 1 1 d . . . . .
H14 H 0.703623 0.476594 0.538345 0.053 Uiso 1 1 calc R U . . .
C10 C 0.78032(6) 0.38514(13) 0.65651(8) 0.0429(3) Uani 1 1 d . . . . .
C16 C 0.61232(6) 0.66584(12) 0.62729(8) 0.0414(3) Uani 1 1 d . . . . .
C19 C 0.54616(6) 0.71914(14) 0.49532(8) 0.0451(3) Uani 1 1 d . . . . .
C15 C 0.63142(6) 0.58528(13) 0.51686(8) 0.0439(3) Uani 1 1 d . . . . .
H15 H 0.620927 0.580847 0.462847 0.053 Uiso 1 1 calc R U . . .
C3 C 0.80104(7) 0.46506(15) 0.82809(9) 0.0511(3) Uani 1 1 d . . . . .
H3 H 0.830019 0.511188 0.815392 0.061 Uiso 1 1 calc R U . . .
C20 C 0.55211(7) 0.79755(15) 0.43647(9) 0.0520(4) Uani 1 1 d D . . . .
F1 F 0.4902(5) 0.9702(8) 0.3909(8) 0.136(3) Uani 0.574(19) 1 d D . P A 1
C5 C 0.70581(7) 0.35949(15) 0.78910(9) 0.0513(3) Uani 1 1 d . . . . .
H5 H 0.670725 0.334182 0.750114 0.062 Uiso 1 1 calc R U . . .
C11 C 0.76834(8) 0.26224(14) 0.63793(10) 0.0527(4) Uani 1 1 d . . . . .
H11 H 0.735347 0.223833 0.645985 0.063 Uiso 1 1 calc R U . . .
C1 C 0.76722(8) 0.36615(16) 0.92394(9) 0.0570(4) Uani 1 1 d . . . . .
H1 H 0.773566 0.345041 0.975707 0.068 Uiso 1 1 calc R U . . .
F4 F 0.39890(19) 0.7460(10) 0.3806(3) 0.1069(19) Uani 0.574(19) 1 d D . P A 1
F3 F 0.4289(4) 0.8870(6) 0.4666(3) 0.1037(18) Uani 0.574(19) 1 d D . P A 1
C23 C 0.48630(7) 0.69748(17) 0.49279(10) 0.0567(4) Uani 1 1 d D . . . .
C6 C 0.71499(8) 0.32918(16) 0.86660(10) 0.0568(4) Uani 1 1 d . . . . .
H6 H 0.685896 0.284020 0.879674 0.068 Uiso 1 1 calc R U . . .
C9 C 0.82857(8) 0.44321(16) 0.64373(11) 0.0575(4) Uani 1 1 d . . . . .
H9 H 0.836509 0.526504 0.656181 0.069 Uiso 1 1 calc R U . . .
C2 C 0.81002(8) 0.43410(17) 0.90506(10) 0.0596(4) Uani 1 1 d . . . . .
H2 H 0.845097 0.459331 0.944083 0.071 Uiso 1 1 calc R U . . .
C18 C 0.57743(8) 0.75260(17) 0.66025(10) 0.0586(4) Uani 1 1 d . . . . .
H18A H 0.574214 0.831768 0.635035 0.088 Uiso 1 1 calc R U . . .
H18B H 0.597958 0.762204 0.715266 0.088 Uiso 1 1 calc R U . . .
H18C H 0.537658 0.719641 0.651642 0.088 Uiso 1 1 calc R U . . .
C12 C 0.80576(10) 0.19596(17) 0.60709(11) 0.0649(5) Uani 1 1 d . . . . .
H12 H 0.798162 0.112434 0.595102 0.078 Uiso 1 1 calc R U . . .
C7 C 0.85387(10) 0.25262(19) 0.59415(12) 0.0699(5) Uani 1 1 d . . . . .
H7 H 0.878802 0.207765 0.573312 0.084 Uiso 1 1 calc R U . . .
C8 C 0.86520(9) 0.3756(2) 0.61199(13) 0.0699(5) Uani 1 1 d . . . . .
H8 H 0.897702 0.414126 0.602745 0.084 Uiso 1 1 calc R U . . .
C21 C 0.4904(4) 0.8452(9) 0.3895(5) 0.075(2) Uani 0.574(19) 1 d D . P A 1
C22 C 0.4497(4) 0.7943(8) 0.4326(5) 0.073(2) Uani 0.574(19) 1 d D . P A 1
C21A C 0.4853(4) 0.8446(9) 0.3946(5) 0.065(3) Uani 0.426(19) 1 d D . P A 2
F2A F 0.4720(6) 0.8382(17) 0.3180(5) 0.122(4) Uani 0.426(19) 1 d D . P A 2
C22A C 0.4434(4) 0.7675(13) 0.4240(6) 0.072(3) Uani 0.426(19) 1 d D . P A 2
F1A F 0.4801(7) 0.9657(9) 0.4079(10) 0.131(5) Uani 0.426(19) 1 d D . P A 2
F4A F 0.4104(6) 0.6833(16) 0.3726(5) 0.127(4) Uani 0.426(19) 1 d D . P A 2
F3A F 0.4048(6) 0.8337(19) 0.4480(8) 0.139(5) Uani 0.426(19) 1 d D . P A 2


_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
N2 C16 1.3677(17) . ?
N2 C19 1.4317(17) . ?
N2 C15 1.3584(17) . ?
O1 C20 1.228(2) . ?
N1 C13 1.3554(17) . ?
N1 C4 1.4423(17) . ?
N1 C10 1.4443(17) . ?
O2 C23 1.227(2) . ?
F2 C21 1.334(9) . ?
C13 C17 1.4063(18) . ?
C13 C14 1.4087(19) . ?
C17 H17 0.9300 . ?
C17 C16 1.3677(19) . ?
C4 C3 1.378(2) . ?
C4 C5 1.383(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.350(2) . ?
C10 C11 1.374(2) . ?
C10 C9 1.377(2) . ?
C16 C18 1.492(2) . ?
C19 C20 1.406(2) . ?
C19 C23 1.407(2) . ?
C15 H15 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.384(2) . ?
C20 C21 1.504(8) . ?
C20 C21A 1.578(8) . ?
F1 C21 1.349(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(2) . ?
C1 H1 0.9300 . ?
C1 C6 1.377(3) . ?
C1 C2 1.374(3) . ?
F4 C22 1.353(8) . ?
F3 C22 1.348(7) . ?
C23 C22 1.549(8) . ?
C23 C22A 1.519(9) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.388(2) . ?
C2 H2 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C7 1.369(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(3) . ?
C8 H8 0.9300 . ?
C21 C22 1.522(8) . ?
C21A F2A 1.322(10) . ?
C21A C22A 1.514(10) . ?
C21A F1A 1.342(9) . ?
C22A F4A 1.348(11) . ?
C22A F3A 1.333(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
C16 N2 C19 122.29(11) . . ?
C15 N2 C16 119.96(11) . . ?
C15 N2 C19 117.75(11) . . ?
C13 N1 C4 122.54(11) . . ?
C13 N1 C10 120.34(11) . . ?
C4 N1 C10 116.27(10) . . ?
N1 C13 C17 121.88(12) . . ?
N1 C13 C14 121.34(12) . . ?
C17 C13 C14 116.78(12) . . ?
C13 C17 H17 119.1 . . ?
C16 C17 C13 121.81(12) . . ?
C16 C17 H17 119.1 . . ?
C3 C4 N1 119.65(13) . . ?
C3 C4 C5 120.11(13) . . ?
C5 C4 N1 120.15(13) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.72(12) . . ?
C15 C14 H14 120.1 . . ?
C11 C10 N1 119.33(13) . . ?
C11 C10 C9 120.63(14) . . ?
C9 C10 N1 120.04(13) . . ?
N2 C16 C18 119.06(12) . . ?
C17 C16 N2 119.20(12) . . ?
C17 C16 C18 121.72(13) . . ?
C20 C19 N2 121.52(13) . . ?
C20 C19 C23 115.09(14) . . ?
C23 C19 N2 123.04(14) . . ?
N2 C15 H15 118.8 . . ?
C14 C15 N2 122.34(12) . . ?
C14 C15 H15 118.8 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.92(15) . . ?
C2 C3 H3 120.0 . . ?
O1 C20 C19 130.71(15) . . ?
O1 C20 C21 120.7(4) . . ?
O1 C20 C21A 126.1(4) . . ?
C19 C20 C21 108.5(4) . . ?
C19 C20 C21A 103.2(4) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.67(14) . . ?
C6 C5 H5 120.2 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.50(15) . . ?
C12 C11 H11 120.3 . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.30(15) . . ?
O2 C23 C19 131.57(16) . . ?
O2 C23 C22 125.2(4) . . ?
O2 C23 C22A 119.3(4) . . ?
C19 C23 C22 102.9(4) . . ?
C19 C23 C22A 109.0(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 C5 119.86(15) . . ?
C1 C6 H6 120.1 . . ?
C10 C9 H9 120.5 . . ?
C10 C9 C8 119.05(16) . . ?
C8 C9 H9 120.5 . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.13(15) . . ?
C1 C2 H2 119.9 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C12 H12 119.8 . . ?
C7 C12 C11 120.40(17) . . ?
C7 C12 H12 119.8 . . ?
C12 C7 H7 120.1 . . ?
C12 C7 C8 119.84(16) . . ?
C8 C7 H7 120.1 . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.57(17) . . ?
C7 C8 H8 119.7 . . ?
F2 C21 C20 113.4(7) . . ?
F2 C21 F1 107.9(9) . . ?
F2 C21 C22 112.0(8) . . ?
C20 C21 C22 103.5(6) . . ?
F1 C21 C20 109.8(8) . . ?
F1 C21 C22 110.1(8) . . ?
F4 C22 C23 112.7(6) . . ?
F4 C22 C21 109.6(7) . . ?
F3 C22 F4 103.8(5) . . ?
F3 C22 C23 112.0(6) . . ?
F3 C22 C21 110.5(7) . . ?
C21 C22 C23 108.1(6) . . ?
F2A C21A C20 109.9(9) . . ?
F2A C21A C22A 112.9(10) . . ?
F2A C21A F1A 103.7(10) . . ?
C22A C21A C20 108.0(6) . . ?
F1A C21A C20 111.2(9) . . ?
F1A C21A C22A 111.2(10) . . ?
C21A C22A C23 103.5(6) . . ?
F4A C22A C23 107.8(8) . . ?
F4A C22A C21A 114.5(8) . . ?
F3A C22A C23 109.5(7) . . ?
F3A C22A C21A 114.3(9) . . ?
F3A C22A F4A 107.1(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C19 C20 O1 -0.5(3) . . . . ?
N2 C19 C20 C21 177.8(4) . . . . ?
N2 C19 C20 C21A -179.9(4) . . . . ?
N2 C19 C23 O2 1.9(3) . . . . ?
N2 C19 C23 C22 175.5(3) . . . . ?
N2 C19 C23 C22A -173.0(6) . . . . ?
O1 C20 C21 F2 61.7(9) . . . . ?
O1 C20 C21 F1 -59.1(9) . . . . ?
O1 C20 C21 C22 -176.7(4) . . . . ?
O1 C20 C21A F2A 46.0(11) . . . . ?
O1 C20 C21A C22A 169.5(7) . . . . ?
O1 C20 C21A F1A -68.2(11) . . . . ?
N1 C13 C17 C16 -178.93(13) . . . . ?
N1 C13 C14 C15 176.50(14) . . . . ?
N1 C4 C3 C2 -176.23(14) . . . . ?
N1 C4 C5 C6 176.51(13) . . . . ?
N1 C10 C11 C12 -179.10(15) . . . . ?
N1 C10 C9 C8 179.80(15) . . . . ?
O2 C23 C22 F4 -50.9(7) . . . . ?
O2 C23 C22 F3 65.8(7) . . . . ?
O2 C23 C22 C21 -172.2(5) . . . . ?
O2 C23 C22A C21A 177.0(6) . . . . ?
O2 C23 C22A F4A -61.4(9) . . . . ?
O2 C23 C22A F3A 54.7(10) . . . . ?
F2 C21 C22 F4 -12.0(11) . . . . ?
F2 C21 C22 F3 -125.8(8) . . . . ?
F2 C21 C22 C23 111.2(8) . . . . ?
C13 N1 C4 C3 -120.57(15) . . . . ?
C13 N1 C4 C5 62.81(19) . . . . ?
C13 N1 C10 C11 -95.25(17) . . . . ?
C13 N1 C10 C9 84.72(19) . . . . ?
C13 C17 C16 N2 2.0(2) . . . . ?
C13 C17 C16 C18 -176.27(14) . . . . ?
C13 C14 C15 N2 3.0(2) . . . . ?
C17 C13 C14 C15 -4.4(2) . . . . ?
C4 N1 C13 C17 16.7(2) . . . . ?
C4 N1 C13 C14 -164.16(13) . . . . ?
C4 N1 C10 C11 74.47(18) . . . . ?
C4 N1 C10 C9 -105.56(16) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C14 C13 C17 C16 1.9(2) . . . . ?
C10 N1 C13 C17 -174.21(13) . . . . ?
C10 N1 C13 C14 4.9(2) . . . . ?
C10 N1 C4 C3 69.96(17) . . . . ?
C10 N1 C4 C5 -106.67(15) . . . . ?
C10 C11 C12 C7 -0.9(3) . . . . ?
C10 C9 C8 C7 -0.5(3) . . . . ?
C16 N2 C19 C20 125.50(16) . . . . ?
C16 N2 C19 C23 -61.6(2) . . . . ?
C16 N2 C15 C14 1.1(2) . . . . ?
C19 N2 C16 C17 176.86(13) . . . . ?
C19 N2 C16 C18 -4.8(2) . . . . ?
C19 N2 C15 C14 -179.30(14) . . . . ?
C19 C20 C21 F2 -116.8(8) . . . . ?
C19 C20 C21 F1 122.4(7) . . . . ?
C19 C20 C21 C22 4.8(7) . . . . ?
C19 C20 C21A F2A -134.6(10) . . . . ?
C19 C20 C21A C22A -11.0(9) . . . . ?
C19 C20 C21A F1A 111.2(10) . . . . ?
C19 C23 C22 F4 135.0(5) . . . . ?
C19 C23 C22 F3 -108.4(6) . . . . ?
C19 C23 C22 C21 13.7(7) . . . . ?
C19 C23 C22A C21A -7.3(11) . . . . ?
C19 C23 C22A F4A 114.3(9) . . . . ?
C19 C23 C22A F3A -129.6(10) . . . . ?
C15 N2 C16 C17 -3.6(2) . . . . ?
C15 N2 C16 C18 174.73(14) . . . . ?
C15 N2 C19 C20 -54.07(19) . . . . ?
C15 N2 C19 C23 118.85(16) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C20 C19 C23 O2 175.23(19) . . . . ?
C20 C19 C23 C22 -11.2(4) . . . . ?
C20 C19 C23 C22A 0.3(6) . . . . ?
C20 C21 C22 F4 -134.5(7) . . . . ?
C20 C21 C22 F3 111.6(7) . . . . ?
C20 C21 C22 C23 -11.3(8) . . . . ?
C20 C21A C22A C23 11.1(12) . . . . ?
C20 C21A C22A F4A -105.9(11) . . . . ?
C20 C21A C22A F3A 130.1(10) . . . . ?
F1 C21 C22 F4 108.1(10) . . . . ?
F1 C21 C22 F3 -5.8(10) . . . . ?
F1 C21 C22 C23 -128.7(8) . . . . ?
C5 C4 C3 C2 0.4(2) . . . . ?
C11 C10 C9 C8 -0.2(3) . . . . ?
C11 C12 C7 C8 0.2(3) . . . . ?
C23 C19 C20 O1 -173.99(18) . . . . ?
C23 C19 C20 C21 4.4(5) . . . . ?
C23 C19 C20 C21A 6.6(5) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
F2A C21A C22A C23 132.8(11) . . . . ?
F2A C21A C22A F4A 15.8(14) . . . . ?
F2A C21A C22A F3A -108.2(12) . . . . ?
F1A C21A C22A C23 -111.1(10) . . . . ?
F1A C21A C22A F4A 131.9(11) . . . . ?
F1A C21A C22A F3A 7.8(12) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 116 electrons were 
found in a volume of 496Å³ in 1 void per unit cell. 
This is consistent with the presence of 
1.5[H2O] per formula unit 
which account for 120 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.059 0.250 124.2 29.4 '3 water'
2 0.000 0.059 0.750 124.2 29.4 '3 water'
3 0.500 0.441 0.250 124.2 29.4 '3 water'
4 0.500 0.559 0.750 124.2 29.4 '3 water'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 'oil on loop'
_olex2_submission_original_sample_id Jx4_2
_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 2.124
_oxdiff_exptl_absorpt_empirical_full_min 0.327
