# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_exp_2986
_database_code_depnum_ccdc_archive 'CCDC 2404419'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2024-11-21 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_audit_creation_date             2022-03-15
_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        1,4-dichlorotetrafluorobenzene
_chemical_formula_moiety         'C6 Cl2 F4'
_chemical_formula_sum            'C6 Cl2 F4'
_chemical_formula_weight         218.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6F4Cl2
_chemical_oxdiff_usercomment     
'Recrystallized from filtered p-xylene solution'
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'
Cl Cl 0.3639 0.7018 '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'

_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.0094(4)
_cell_length_b                   7.6502(4)
_cell_length_c                   5.0908(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.673(4)
_cell_angle_gamma                90
_cell_volume                     347.74(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1768
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.0260
_cell_measurement_theta_min      7.5720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.634
_exptl_absorpt_correction_T_max  0.636
_exptl_absorpt_correction_T_min  0.169
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.091
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             212
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -4 1 0.1397
-2 4 -1 0.1228
2 -3 2 0.1195
1 0 3 0.0971
-1 -1 -3 0.0939
0 2 3 0.1047
-4 3 1 0.1187
-3 -4 0 0.1279
-6 -1 1 0.1468
5 -2 -1 0.1452
5 3 -1 0.0955
-3 -2 3 0.1213
3 2 -3 0.1246
3 -2 -3 0.1383
-1 5 0 0.1312
-1 0 3 0.1054
-1 1 3 0.1088
1 -2 -3 0.1170
0 2 -3 0.1250
0 -2 3 0.1167
-2 1 -3 0.1113
2 3 2 0.1052
3 0 2 0.1134
4 -3 2 0.1237
3 -4 1 0.1349
-2 -2 -3 0.1044
-3 0 -3 0.1017
-4 2 -2 0.1068
3 3 2 0.0973
-3 -3 -2 0.1105
5 0 1 0.1181
5 -2 1 0.1350
-5 1 -1 0.1189
4 -4 0 0.1438
-2 5 1 0.1240
1 5 1 0.1199
0 -5 0 0.1358
-2 -4 1 0.1218
-4 -3 2 0.1167
-4 0 2 0.1209

_exptl_crystal_preparation       'Evaporation from benzene to dryness'
_exptl_crystal_recrystallization_method 'Grown from benzene solvent'
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.194
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.3627 -4.1407 1.0552 0.2930 -0.4998 -0.8151
-2.4029 3.7433 -1.4983 -0.3548 0.6041 0.7136
2.3042 -2.6838 2.2596 0.4503 -0.7648 -0.4609
1.3733 0.2989 3.0717 0.4991 -0.8447 0.1936
-1.2132 -0.6673 -3.0800 -0.4899 0.8288 -0.2705
0.2767 2.4751 2.8131 0.3940 -0.6648 0.6346
-4.4205 3.0355 1.1098 -0.5038 -0.2111 0.8376
-3.4249 -4.0197 0.1225 -0.7414 -0.3066 -0.5969
-5.6615 -1.0732 0.8473 -0.9186 -0.3817 0.1027
4.9085 -2.4502 -1.1258 0.6101 0.2550 -0.7502
4.8163 2.8089 -0.5013 0.8859 0.3673 0.2833
-2.7881 -1.6847 2.8651 -0.2998 -0.9539 -0.0091
2.7881 1.6847 -2.8651 0.2998 0.9539 0.0091
3.1035 -2.4118 -2.5103 0.1959 0.6288 -0.7525
-1.0256 4.8881 0.1818 0.0668 0.2054 0.9764
-0.9009 0.0157 3.3024 0.1276 -0.9583 0.2556
-1.2654 1.2964 3.1756 0.1146 -0.8558 0.5044
1.3872 -1.7891 -3.0587 -0.1069 0.7966 -0.5949
0.1601 2.0829 -2.9819 -0.1286 0.9728 0.1925
-0.3565 -1.5764 3.1243 0.1309 -0.9882 -0.0794
-1.8975 1.4260 -2.8065 -0.4856 0.8573 0.1711
1.5663 2.7076 2.4820 0.5911 -0.5389 0.6001
3.3374 -0.4782 2.4171 0.7353 -0.6728 -0.0815
3.6067 -2.5825 1.6627 0.6213 -0.5698 -0.5378
3.3338 -3.6458 0.9584 0.4687 -0.4309 -0.7711
-2.3707 -1.6175 -2.6166 -0.6866 0.6269 -0.3682
-3.1725 -0.0069 -2.5099 -0.7377 0.6747 -0.0230
-3.5988 1.7722 -2.0290 -0.6875 0.6299 0.3614
3.3002 3.0712 1.5405 0.8169 -0.2246 0.5312
-3.3245 -3.0498 -1.5405 -0.8200 0.2255 -0.5261
5.0249 0.4753 1.2657 0.9626 -0.2661 -0.0509
5.1285 -1.6736 0.7368 0.8379 -0.2326 -0.4937
-5.2150 0.5723 -1.0396 -0.9277 0.2569 0.2709
3.8065 -3.7627 -0.1010 0.4532 -0.1271 -0.8823
-2.2712 4.5219 0.6456 -0.1180 0.0347 0.9924
0.5591 4.8172 0.6919 0.3696 0.0774 0.9260
-0.1249 -4.9569 0.2055 -0.2286 -0.3364 -0.9136
-1.9343 -4.4053 1.1998 -0.4210 -0.6160 -0.6658
-3.7441 -2.5412 2.1582 -0.5568 -0.8123 -0.1735
-4.4323 0.0329 2.4716 -0.5280 -0.7686 0.3612

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1936
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.141
_diffrn_reflns_theta_min         7.626
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  26.00   1.00    1.00    --   38.00  90.00  57.36   25
  2  ω    -67.00   8.00   1.00    1.00    --  -42.37  38.00   0.00   75
  3  ω     31.00  75.00   1.00    1.00    --   42.37-125.00 150.00   44
  4  ω    -21.00  43.00   1.00    1.00    --   42.37 -77.00  60.00   64
  5  ω      7.00  63.00   1.00    1.00    --   42.37 -99.00-150.00   56
  6  ω     91.00 117.00   1.00    1.00    --   50.00  60.00 -79.59   26
  7  ω     21.00  53.00   1.00    1.00    --   50.00  71.00 110.96   32
  8  ω     58.00  84.00   1.00    1.00    --   50.00  60.00 -79.59   26
  9  ω     21.00  46.00   1.00    1.00    --   50.00  60.00 -79.59   25
 10  ω     16.00  41.00   1.00    1.00    --   50.00  82.00 -73.29   25
 11  ω     16.00  42.00   1.00    1.00    --   50.00  82.00  58.20   26
 12  ω     22.00  52.00   1.00    1.00    --   50.00  67.00 171.74   30
 13  ω     74.00 117.00   1.00    1.00    --   50.00  67.00 171.74   43
 14  ω     16.00  42.00   1.00    1.00    --   50.00  81.00-145.68   26
 15  ω     27.00  75.00   1.00    1.00    --   54.00  58.00   9.66   48
 16  ω     77.00 104.00   1.00    1.00    --   54.00  65.00 -11.17   27
 17  ω     24.00  50.00   1.00    1.00    --   54.00  65.00 -11.17   26
 18  ω     91.00 123.00   1.00    1.00    --   54.00  58.00   9.66   32
 19  ω     68.00  96.00   1.00    1.00    --   74.00  61.00  98.84   28
 20  ω     58.00 100.00   1.00    1.00    --   86.00  61.00  72.14   42
 21  ω     76.00 108.00   1.00    1.00    --  105.44  61.00-180.00   32
 22  ω     87.00 112.00   1.00    1.00    --  105.44  61.00 -60.00   25
 23  ω    131.00 178.00   1.00    1.00    --  105.44  77.00   0.00   47
 24  ω     82.00 159.00   1.00    1.00    --  105.44  61.00 -90.00   77
 25  ω     39.00 134.00   1.00    1.00    --  105.44 -61.00 -90.00   95
 26  ω     38.00 100.00   1.00    1.00    --  105.44 -95.00 150.00   62
 27  ω     81.00 107.00   1.00    1.00    --  105.44  45.00  30.00   26
 28  ω    127.00 176.00   1.00    1.00    --  105.44  61.00 -60.00   49
 29  ω     26.00  75.00   1.00    1.00    --  105.44 -95.00  90.00   49
 30  ω     80.00 161.00   1.00    1.00    --  105.44  45.00-150.00   81
 31  ω     81.00 120.00   1.00    1.00    --  105.44  45.00  60.00   39
 32  ω     76.00 111.00   1.00    1.00    --  105.44  61.00  90.00   35
 33  ω     76.00 157.00   1.00    1.00    --  105.44  61.00-120.00   81
 34  ω     77.00 150.00   1.00    1.00    --  105.44  61.00 120.00   73
 35  ω     77.00 104.00   1.00    1.00    --  105.44  61.00-150.00   27
 36  ω     87.00 113.00   1.00    1.00    --  105.44  45.00   0.00   26
 37  ω     77.00 103.00   1.00    1.00    --  105.44  61.00 -30.00   26
 38  ω    125.00 168.00   1.00    1.00    --  105.44  77.00 -30.00   43
 39  ω     77.00 104.00   1.00    1.00    --  105.44  61.00  30.00   27
 40  ω     82.00 112.00   1.00    1.00    --  105.44-125.00 -60.00   30
 41  ω     85.00 110.00   1.00    1.00    --  105.44-125.00  60.00   25
 42  ω    132.00 178.00   1.00    1.00    --  105.44  45.00  60.00   46
 43  ω     51.00  78.00   1.00    1.00    --  105.44-125.00 -60.00   27
 44  ω    120.00 149.00   1.00    1.00    --  105.44  61.00 150.00   29
 45  ω     78.00 105.00   1.00    1.00    --  105.44  61.00 150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1661740000
_diffrn_orient_matrix_UB_12      0.0454122000
_diffrn_orient_matrix_UB_13      0.0837589000
_diffrn_orient_matrix_UB_21      0.0139791000
_diffrn_orient_matrix_UB_22      0.0556210000
_diffrn_orient_matrix_UB_23      -0.2866424000
_diffrn_orient_matrix_UB_31      -0.0441535000
_diffrn_orient_matrix_UB_32      0.1880852000
_diffrn_orient_matrix_UB_33      0.0644613000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                364
_reflns_number_total             368
_reflns_odcompleteness_completeness 97.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_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         0.260
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     31
_refine_ls_number_reflns         368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0220
_refine_ls_restrained_S_all      1.168
_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)+(0.0314P)²+0.2678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0596
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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
Cl1 Cl 0.23788(5) 0.0000 -0.38996(9) 0.0297(2) Uani 1 2 d S T P . .
F1 F 0.10153(10) -0.30772(11) -0.16995(18) 0.0314(3) Uani 1 1 d . . . . .
C1 C 0.1071(2) 0.0000 -0.1751(4) 0.0212(4) Uani 1 2 d S T P . .
C2 C 0.05267(15) -0.15523(18) -0.0866(3) 0.0223(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0260(3) 0.0409(4) 0.0246(3) 0.000 0.01253(19) 0.000
F1 0.0364(5) 0.0227(5) 0.0372(5) -0.0058(4) 0.0122(4) 0.0050(4)
C1 0.0186(8) 0.0275(10) 0.0182(9) 0.000 0.0050(7) 0.000
C2 0.0227(6) 0.0210(7) 0.0229(7) -0.0028(5) 0.0027(5) 0.0025(5)

_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
Cl1 C1 1.7110(19) . ?
F1 C2 1.3359(16) . ?
C1 C2 1.3831(17) 6 ?
C1 C2 1.3831(17) . ?
C2 C2 1.379(3) 2 ?

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
C2 C1 Cl1 120.84(9) 6 . ?
C2 C1 Cl1 120.84(9) . . ?
C2 C1 C2 118.31(17) 6 . ?
F1 C2 C1 120.00(12) . . ?
F1 C2 C2 119.15(7) . 2 ?
C2 C2 C1 120.84(9) 2 . ?

_shelx_res_file                  
;
    exp_2986.res created by SHELXL-2014/7

TITL exp_2986_a.res in C2/m
REM Old TITL exp_2986 in C2/m
REM SHELXT solution in C2/m
REM R1 0.098, Rweak 0.012, Alpha 0.046, Orientation as input
REM Formula found by SHELXT: C3 F2 Cl
CELL 1.54184 9.0094 7.6502 5.0908 90 97.673 90
ZERR 2 0.0004 0.0004 0.0002 0 0.004 0
LATT 7
SYMM -X,+Y,-Z
SFAC C Cl F
UNIT 12 4 8

L.S. 10
PLAN  4
list 4
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\exp_2986.hkl">
REM </olex2.extras>

WGHT    0.031400    0.267800
FVAR       1.68453
CL1   2    0.237883    0.000000   -0.389961    10.50000    0.02604    0.04088 =
         0.02464    0.00000    0.01253    0.00000
F1    3    0.101535   -0.307723   -0.169947    11.00000    0.03635    0.02270 =
         0.03720   -0.00581    0.01224    0.00498
C1    1    0.107149    0.000000   -0.175119    10.50000    0.01856    0.02751 =
         0.01820    0.00000    0.00498    0.00000
C2    1    0.052672   -0.155229   -0.086631    11.00000    0.02274    0.02104 =
         0.02290   -0.00280    0.00268    0.00246
HKLF 4

REM  exp_2986_a.res in C2/m
REM R1 =  0.0220 for     364 Fo > 4sig(Fo)  and  0.0221 for all     368 data
REM     31 parameters refined using      0 restraints

END

WGHT      0.0314      0.2678

REM Highest difference peak  0.260,  deepest hole -0.172,  1-sigma level  0.049
Q1    1   0.0000 -0.1552  0.0000  10.50000  0.05    0.26
Q2    1   0.1713  0.0000 -0.2619  10.50000  0.05    0.25
Q3    1   0.1476  0.0000 -0.5541  10.50000  0.05    0.24
Q4    1   0.0774  0.0739 -0.1322  11.00000  0.05    0.20
;
_shelx_res_checksum              14983
_olex2_date_sample_data_collection 2021-12-08
_olex2_exptl_crystal_mounting_method '0.3mm Hampton Research nylon loop'
_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 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.819
####################################################################### 
# 
# 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_exp_2991
_database_code_depnum_ccdc_archive 'CCDC 2404421'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2024-11-21 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_audit_creation_date             2022-03-29
_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        Chloropentafluorobenzene
_chemical_formula_moiety         'C6 Cl F5'
_chemical_formula_sum            'C6 Cl F5'
_chemical_formula_weight         202.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6F5Cl
_chemical_oxdiff_usercomment     
'Liquid in 0.3mm capillary, centrifuge, nucleated at 240K -> 200K -> 150K'
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'
Cl Cl 0.3639 0.7018 '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'

_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.0176(3)
_cell_length_b                   7.6579(3)
_cell_length_c                   9.4977(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.562(3)
_cell_angle_gamma                90
_cell_volume                     651.58(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3394
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.8260
_cell_measurement_theta_min      4.6740
_shelx_estimated_absorpt_T_max   0.252
_shelx_estimated_absorpt_T_min   0.075
_exptl_absorpt_coefficient_mu    5.690
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.066
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.064
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 4 0 0.1902
4 -4 0 0.1574
3 3 3 0.1787
-4 -3 -3 0.1590
3 2 -5 0.4704
-3 -2 6 0.4655
5 -2 1 0.1525
-5 2 -1 0.2017
5 1 2 0.1574
-5 -1 -2 0.1918
1 4 2 0.1787
-1 -4 -2 0.1508
-2 5 1 0.1885
2 -5 -1 0.1508

_exptl_crystal_preparation       'Liquid sealed in 0.3mm X-ray capillary'
_exptl_crystal_recrystallization_method 'Grown in situ from the melt'
_exptl_crystal_size_max          0.947
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.334
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.0564 3.5721 0.1350 0.2324 0.9723 0.0253
4.0487 -3.5773 -0.1172 -0.2325 -0.9724 -0.0221
3.4986 3.0718 2.7060 0.9725 -0.2325 -0.0094
-3.5042 -3.0752 -2.6934 -0.9725 0.2325 0.0116
2.5384 1.5786 -5.4710 0.0160 -0.0015 -0.9999
-2.5030 -1.5461 5.5005 -0.0058 -0.0008 1.0000
5.2350 -1.6408 1.2129 0.2681 -0.9631 -0.0232
-5.2162 1.6531 -1.2564 -0.2681 0.9633 0.0153
5.0612 0.8758 2.2675 0.7259 -0.6875 -0.0222
-5.0478 -0.8673 -2.2986 -0.7259 0.6876 0.0166
1.1037 4.4256 2.4088 0.9634 0.2681 -0.0002
-1.0809 -4.4115 -2.4593 -0.9634 -0.2681 -0.0090
-1.8095 4.6409 1.3349 0.6749 0.7379 0.0003
1.8310 -4.6275 -1.3828 -0.6749 -0.7379 -0.0090

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3896
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.004
_diffrn_reflns_theta_min         4.687
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  23.00   1.00    1.00    --   34.00  92.00  71.60   27
  2  ω      8.00  41.00   1.00    1.00    --   42.00  81.00-101.61   33
  3  ω    -67.00  31.00   1.00    1.00    --  -42.37  38.00-180.00   98
  4  ω     27.00  94.00   1.00    1.00    --   42.37-125.00 -30.00   67
  5  ω     31.00  57.00   1.00    1.00    --   42.37  38.00-180.00   26
  6  ω     73.00  98.00   1.00    1.00    --   42.37-125.00  60.00   25
  7  ω     32.00  60.00   1.00    1.00    --   42.37-125.00  60.00   28
  8  ω     13.00  42.00   1.00    1.00    --   46.00  81.00 -37.29   29
  9  ω     16.00  42.00   1.00    1.00    --   46.00  68.00-111.70   26
 10  ω     13.00  38.00   1.00    1.00    --   46.00  78.00  48.63   25
 11  ω     16.00  41.00   1.00    1.00    --   50.00  81.00 142.47   25
 12  ω    102.00 127.00   1.00    1.00    --   54.00  67.00  98.68   25
 13  ω     25.00  51.00   1.00    1.00    --   54.00  67.00  98.68   26
 14  ω     82.00 127.00   1.00    1.00    --   58.00  69.00  -2.04   45
 15  ω     39.00  65.00   1.00    1.00    --   58.00  69.00  -2.04   26
 16  ω     93.00 130.00   1.00    1.00    --   58.00  70.00  57.95   37
 17  ω     27.00  70.00   1.00    1.00    --   58.00  70.00  57.95   43
 18  ω     91.00 117.00   1.00    1.00    --   66.00  70.00 152.59   26
 19  ω     40.00  78.00   1.00    1.00    --   66.00  54.00-100.12   38
 20  ω     37.00  73.00   1.00    1.00    --   66.00  65.00 -46.56   36
 21  ω     53.00 138.00   1.00    1.00    --   66.00  61.00-178.88   85
 22  ω     35.00  66.00   1.00    1.00    --   66.00  70.00 152.59   31
 23  ω     49.00  77.00   1.00    1.00    --   78.00  62.00  88.56   28
 24  ω     77.00 123.00   1.00    1.00    --  105.44  61.00-150.00   46
 25  ω    101.00 150.00   1.00    1.00    --  105.44 125.00  30.00   49
 26  ω     79.00 144.00   1.00    1.00    --  105.44  61.00 -30.00   65
 27  ω    117.00 149.00   1.00    1.00    --  105.44  61.00   0.00   32
 28  ω     25.00 100.00   1.00    1.00    --  105.44 -95.00 -30.00   75
 29  ω     77.00 110.00   1.00    1.00    --  105.44  61.00   0.00   33
 30  ω    126.00 178.00   1.00    1.00    --  105.44  61.00-150.00   52
 31  ω     76.00 102.00   1.00    1.00    --  105.44  61.00  30.00   26
 32  ω     84.00 110.00   1.00    1.00    --  105.44  45.00 -60.00   26
 33  ω     41.00 105.00   1.00    1.00    --  105.44 -95.00  60.00   64
 34  ω     86.00 139.00   1.00    1.00    --  105.44  45.00  60.00   53
 35  ω    124.00 178.00   1.00    1.00    --  105.44  77.00 150.00   54
 36  ω     77.00 148.00   1.00    1.00    --  105.44  61.00  90.00   71
 37  ω     23.00 100.00   1.00    1.00    --  105.44 -95.00-120.00   77
 38  ω     33.00  71.00   1.00    1.00    --  105.44 -95.00 120.00   38
 39  ω    124.00 176.00   1.00    1.00    --  105.44  61.00 -90.00   52
 40  ω     41.00 101.00   1.00    1.00    --  105.44-125.00-150.00   60
 41  ω     80.00 169.00   1.00    1.00    --  105.44  61.00 120.00   89
 42  ω     79.00 119.00   1.00    1.00    --  105.44  61.00-180.00   40
 43  ω     78.00 103.00   1.00    1.00    --  105.44  61.00 -90.00   25
 44  ω     84.00 110.00   1.00    1.00    --  105.44  45.00 -30.00   26
 45  ω     76.00 139.00   1.00    1.00    --  105.44  61.00-120.00   63
 46  ω     76.00 102.00   1.00    1.00    --  105.44  61.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0812026000
_diffrn_orient_matrix_UB_12      0.1542869000
_diffrn_orient_matrix_UB_13      0.0792711000
_diffrn_orient_matrix_UB_21      -0.1409359000
_diffrn_orient_matrix_UB_22      0.1133678000
_diffrn_orient_matrix_UB_23      -0.0324038000
_diffrn_orient_matrix_UB_31      -0.0559727000
_diffrn_orient_matrix_UB_32      -0.0617282000
_diffrn_orient_matrix_UB_33      0.1389773000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                675
_reflns_number_total             699
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_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         0.235
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         699
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.083
_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)+(0.0564P)²+0.4791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_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
Cl1 Cl 0.23659(6) 0.0000 0.06092(7) 0.0381(3) Uani 1 2 d S T P . .
F1 F -0.22267(15) 0.0000 0.44435(17) 0.0440(4) Uani 1 2 d S T P . .
F2 F -0.11364(12) 0.30626(14) 0.35763(14) 0.0432(3) Uani 1 1 d . . . . .
F3 F 0.09804(11) 0.30740(13) 0.17847(13) 0.0399(3) Uani 1 1 d . . . . .
C1 C -0.1168(2) 0.0000 0.3570(3) 0.0297(5) Uani 1 2 d S T P . .
C2 C -0.06211(17) 0.1561(2) 0.31181(19) 0.0287(4) Uani 1 1 d . . . . .
C3 C 0.04716(17) 0.1552(2) 0.22167(18) 0.0270(4) Uani 1 1 d . . . . .
C4 C 0.1026(2) 0.0000 0.1747(2) 0.0259(5) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0260(3) 0.0563(4) 0.0341(4) 0.000 0.0127(2) 0.000
F1 0.0307(7) 0.0671(11) 0.0374(9) 0.000 0.0183(6) 0.000
F2 0.0415(6) 0.0366(6) 0.0519(7) -0.0114(5) 0.0071(5) 0.0131(4)
F3 0.0391(6) 0.0279(5) 0.0531(7) 0.0090(4) 0.0073(5) -0.0052(4)
C1 0.0190(9) 0.0427(13) 0.0282(12) 0.000 0.0068(8) 0.000
C2 0.0243(7) 0.0284(8) 0.0329(9) -0.0041(6) 0.0017(6) 0.0052(6)
C3 0.0224(7) 0.0268(8) 0.0315(9) 0.0029(6) 0.0015(6) -0.0021(5)
C4 0.0179(9) 0.0316(11) 0.0282(12) 0.000 0.0031(8) 0.000

_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
Cl1 C4 1.711(2) . ?
F1 C1 1.334(3) . ?
F2 C2 1.3318(18) . ?
F3 C3 1.3344(18) . ?
C1 C2 1.380(2) 6 ?
C1 C2 1.380(2) . ?
C2 C3 1.377(3) . ?
C3 C4 1.383(2) . ?
C4 C3 1.383(2) 6 ?

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 120.00(11) . 6 ?
F1 C1 C2 120.00(11) . . ?
C2 C1 C2 120.0(2) 6 . ?
F2 C2 C1 119.71(16) . . ?
F2 C2 C3 120.58(14) . . ?
C3 C2 C1 119.71(15) . . ?
F3 C3 C2 118.83(14) . . ?
F3 C3 C4 120.13(15) . . ?
C2 C3 C4 121.03(15) . . ?
C3 C4 Cl1 120.74(10) 6 . ?
C3 C4 Cl1 120.74(10) . . ?
C3 C4 C3 118.5(2) . 6 ?

_shelx_res_file                  
;
    exp_2991.res created by SHELXL-2014/7

TITL exp_2991_a.res in C2/m
REM Old TITL exp_2991_a.res in C2/m
REM SHELXT solution in C2/m
REM R1 0.133, Rweak 0.011, Alpha 0.040, Orientation as input
REM Formula found by SHELXT: C6 F5 Cl
CELL 1.54184 9.0176 7.6579 9.4977 90 96.562 90
ZERR 4 0.0003 0.0003 0.0004 0 0.003 0
LATT 7
SYMM -X,+Y,-Z
SFAC C Cl F
UNIT 24 4 20

L.S. 10
PLAN  2
SIZE 0.334 0.358 0.947
TEMP -123.15
list 4
fmap 2 53
acta
OMIT -6 0 10
OMIT -5 1 10
OMIT -6 0 9
OMIT -2 4 2
REM <olex2.extras>
REM <HklSrc "%.\\exp_2991.hkl">
REM </olex2.extras>

WGHT    0.056400    0.479100
FVAR       0.92460
CL1   2    0.236585    0.000000    0.060916    10.50000    0.02598    0.05634 =
         0.03406    0.00000    0.01268    0.00000
F1    3   -0.222666    0.000000    0.444346    10.50000    0.03068    0.06714 =
         0.03737    0.00000    0.01826    0.00000
F2    3   -0.113641    0.306256    0.357627    11.00000    0.04154    0.03660 =
         0.05187   -0.01141    0.00708    0.01307
F3    3    0.098038    0.307402    0.178474    11.00000    0.03910    0.02789 =
         0.05307    0.00902    0.00726   -0.00519
C1    1   -0.116811    0.000000    0.357039    10.50000    0.01900    0.04270 =
         0.02821    0.00000    0.00676    0.00000
C2    1   -0.062107    0.156098    0.311808    11.00000    0.02435    0.02843 =
         0.03291   -0.00415    0.00165    0.00520
C3    1    0.047164    0.155179    0.221673    11.00000    0.02242    0.02678 =
         0.03152    0.00286    0.00153   -0.00207
C4    1    0.102554    0.000000    0.174697    10.50000    0.01785    0.03158 =
         0.02823    0.00000    0.00313    0.00000
HKLF 4

REM  exp_2991_a.res in C2/m
REM R1 =  0.0343 for     675 Fo > 4sig(Fo)  and  0.0357 for all     699 data
REM     61 parameters refined using      0 restraints

END

WGHT      0.0564      0.4791

REM Highest difference peak  0.235,  deepest hole -0.283,  1-sigma level  0.067
Q1    1   0.0045  0.1559  0.2764  11.00000  0.05    0.24
Q2    1  -0.0593 -0.0764  0.3676  11.00000  0.05    0.22
;
_shelx_res_checksum              1450
_olex2_date_sample_data_collection 2021-12-08
_olex2_exptl_crystal_mounting_method '0.3mm X-ray capillary'
_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 1.598
_oxdiff_exptl_absorpt_empirical_full_min 0.668
####################################################################### 
# 
# 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_exp_2989
_database_code_depnum_ccdc_archive 'CCDC 2404420'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2024-11-21 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_audit_creation_date             2024-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        Chloropentafluorobenzene
_chemical_formula_moiety         'C6 Cl F5'
_chemical_formula_sum            'C6 Cl F5'
_chemical_formula_weight         202.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6F5Cl
_chemical_oxdiff_usercomment     
'Liquid in 0.3mm capillary, centrifuge, nucleated at 240K, then 200K'
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'
Cl Cl 0.3639 0.7018 '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'

_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.1116(6)
_cell_length_b                   7.7713(6)
_cell_length_c                   4.8027(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.977(7)
_cell_angle_gamma                90
_cell_volume                     338.23(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1571
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.5330
_cell_measurement_theta_min      9.8010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.481
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.063
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             196
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 2 3 0.4720
3 -2 -3 0.4671
-4 -4 0 0.1131
-5 -2 -1 0.1115
5 2 1 0.2476
5 -1 1 0.2329
-5 1 -1 0.1312
4 -3 1 0.2001
-4 3 -1 0.1559
1 -5 1 0.1655
-1 5 -1 0.1967
-2 -5 1 0.1377
2 5 -1 0.2245
4 4 0 0.2393

_exptl_crystal_preparation       'Liquid sealed in 0.3mm X-ray capillary'
_exptl_crystal_recrystallization_method 'Grown in situ from the melt'
_exptl_crystal_size_max          0.961
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.357
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.5170 1.5098 2.7868 -0.0003 -0.0093 -1.0000
2.5029 -1.5226 -2.7869 -0.0005 0.0059 1.0000
-4.1056 -3.6185 0.0371 -0.2325 -0.9724 -0.0198
-5.3237 -1.5673 -0.6551 0.2849 -0.9584 -0.0203
5.3168 1.5719 0.6633 -0.2849 0.9584 0.0174
5.1414 -0.9204 1.1414 -0.7258 0.6874 0.0262
-5.1173 0.9048 -1.1701 0.7259 -0.6876 -0.0160
3.5793 -3.1595 1.3255 -0.9723 0.2324 0.0238
-3.6257 3.1880 -1.2694 0.9717 -0.2322 -0.0436
1.0235 -4.5314 1.1941 -0.9586 -0.2849 0.0009
-0.9990 4.5160 -1.2217 0.9585 0.2849 0.0090
-1.7750 -4.7086 0.7056 -0.6877 -0.7260 -0.0090
1.7750 4.7086 -0.7056 0.6877 0.7260 0.0090
4.1285 3.6028 -0.0646 0.2325 0.9721 0.0296

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1277
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2160
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.892
_diffrn_reflns_theta_min         9.796
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  21.00   1.00    1.00    --   34.00  92.00-108.93   25
  2  ω      2.00  27.00   1.00    1.00    --   38.00  88.00 111.78   25
  3  ω    -71.00 -20.00   1.00    1.00    --  -42.37 -38.00-120.00   51
  4  ω   -104.00 -75.00   1.00    1.00    --  -42.37 -38.00-120.00   29
  5  ω   -116.00 -53.00   1.00    1.00    --  -42.37 -57.00 150.00   63
  6  ω     -7.00  28.00   1.00    1.00    --  -42.37  57.00 -90.00   35
  7  ω    -80.00  -7.00   1.00    1.00    --  -42.37 125.00  30.00   73
  8  ω    -71.00 -11.00   1.00    1.00    --  -42.37  57.00 -90.00   60
  9  ω      9.00  34.00   1.00    1.00    --   42.37  80.00   3.93   25
 10  ω     42.00  69.00   1.00    1.00    --   42.37-125.00   0.00   27
 11  ω     12.00  37.00   1.00    1.00    --   46.00  82.00 -11.75   25
 12  ω     15.00  40.00   1.00    1.00    --   46.00  79.00-168.07   25
 13  ω     12.00  37.00   1.00    1.00    --   46.00  82.00  54.08   25
 14  ω     16.00  41.00   1.00    1.00    --   50.00  82.00-124.90   25
 15  ω     77.00 129.00   1.00    1.00    --   58.00  71.00 126.19   52
 16  ω     31.00  65.00   1.00    1.00    --   58.00  71.00 126.19   34
 17  ω     28.00  54.00   1.00    1.00    --   58.00  65.00-120.23   26
 18  ω     35.00  61.00   1.00    1.00    --   66.00  70.00  -2.61   26
 19  ω     42.00  68.00   1.00    1.00    --   70.00  69.00   8.23   26
 20  ω     39.00  78.00   1.00    1.00    --   70.00  71.00  25.21   39
 21  ω     41.00  74.00   1.00    1.00    --   70.00  68.00 153.20   33
 22  ω    113.00 142.00   1.00    1.00    --   70.00  68.00 153.20   29
 23  ω    109.00 143.00   1.00    1.00    --   70.00  71.00 -79.68   34
 24  ω     39.00  69.00   1.00    1.00    --   70.00  71.00 -79.68   30
 25  ω     44.00  80.00   1.00    1.00    --   74.00  69.00  54.66   36
 26  ω     46.00  80.00   1.00    1.00    --   74.00  61.00-111.07   34
 27  ω     57.00  83.00   1.00    1.00    --   86.00  61.00-101.42   26
 28  ω    139.00 171.00   1.00    1.00    --  102.00  61.00 -68.41   32
 29  ω     73.00 126.00   1.00    1.00    --  102.00  61.00 -68.41   53
 30  ω    131.00 157.00   1.00    1.00    --  105.44  61.00 -30.00   26
 31  ω     76.00 113.00   1.00    1.00    --  105.44  62.00  10.62   37
 32  ω     76.00 103.00   1.00    1.00    --  105.44  61.00 -30.00   27
 33  ω     80.00 107.00   1.00    1.00    --  105.44  45.00 150.00   27
 34  ω     24.00 103.00   1.00    1.00    --  105.44 -95.00  30.00   79
 35  ω     87.00 114.00   1.00    1.00    --  105.44  45.00   0.00   27
 36  ω     80.00 109.00   1.00    1.00    --  105.44  61.00 150.00   29
 37  ω     77.00 109.00   1.00    1.00    --  105.44  61.00  30.00   32
 38  ω    136.00 171.00   1.00    1.00    --  105.44  61.00 -90.00   35
 39  ω     96.00 131.00   1.00    1.00    --  105.44 -61.00 150.00   35
 40  ω     36.00  82.00   1.00    1.00    --  105.44 -61.00 150.00   46
 41  ω     85.00 115.00   1.00    1.00    --  105.44  61.00-150.00   30
 42  ω    114.00 174.00   1.00    1.00    --  105.44  77.00 120.00   60
 43  ω     77.00 102.00   1.00    1.00    --  105.44  61.00  90.00   25
 44  ω     23.00 104.00   1.00    1.00    --  105.44 -95.00 120.00   81
 45  ω    141.00 176.00   1.00    1.00    --  105.44  61.00-150.00   35
 46  ω     76.00 102.00   1.00    1.00    --  105.44  61.00 -90.00   26
 47  ω     71.00 105.00   1.00    1.00    --  105.44 -95.00-150.00   34
 48  ω     42.00 112.00   1.00    1.00    --  105.44-125.00   0.00   70
 49  ω    125.00 178.00   1.00    1.00    --  105.44  61.00-180.00   53
 50  ω     78.00 122.00   1.00    1.00    --  105.44  61.00-180.00   44
 51  ω    110.00 177.00   1.00    1.00    --  105.44  61.00  60.00   67
 52  ω     76.00 106.00   1.00    1.00    --  105.44  61.00  60.00   30
 53  ω    122.00 149.00   1.00    1.00    --  105.44  30.00 -90.00   27
 54  ω     90.00 130.00   1.00    1.00    --  105.44  45.00 120.00   40
 55  ω     80.00 107.00   1.00    1.00    --  105.44  30.00 -90.00   27
 56  ω    118.00 177.00   1.00    1.00    --  105.44  62.00  10.62   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0794665000
_diffrn_orient_matrix_UB_12      0.1528249000
_diffrn_orient_matrix_UB_13      -0.1546847000
_diffrn_orient_matrix_UB_21      0.1396465000
_diffrn_orient_matrix_UB_22      0.1109293000
_diffrn_orient_matrix_UB_23      0.0626803000
_diffrn_orient_matrix_UB_31      0.0555465000
_diffrn_orient_matrix_UB_32      -0.0603751000
_diffrn_orient_matrix_UB_33      -0.2759434000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                323
_reflns_number_total             359
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.09(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     32
_refine_ls_number_reflns         359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      1.084
_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)+(0.0801P)²+0.4739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1861
_refine_ls_wR_factor_ref         0.1889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Shared sites
{Cl1, F1}
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(F1)
3. Others
 Fixed Sof: Cl1(0.25) F1(0.25)
;
_atom_sites_solution_hydrogens   .
_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
Cl1 Cl 0.2292(2) 0.0000 -0.3783(4) 0.1069(14) Uani 0.5 2 d S T P . .
F1 F 0.2292(2) 0.0000 -0.3783(4) 0.1069(14) Uani 0.5 2 d S T P . .
F2 F 0.1038(3) -0.3031(4) -0.1829(7) 0.1096(16) Uani 1 1 d . . . . .
C1 C 0.1068(5) 0.0000 -0.1789(11) 0.0731(16) Uani 1 2 d S T P . .
C2 C 0.0537(4) -0.1523(5) -0.0897(8) 0.0750(14) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0875(18) 0.156(3) 0.0811(17) 0.000 0.0265(11) 0.000
F1 0.0875(18) 0.156(3) 0.0811(17) 0.000 0.0265(11) 0.000
F2 0.097(2) 0.0788(19) 0.149(3) -0.0290(15) -0.0064(17) 0.0241(13)
C1 0.055(3) 0.091(4) 0.073(3) 0.000 0.003(2) 0.000
C2 0.066(2) 0.067(2) 0.089(3) -0.0095(16) -0.0061(17) 0.0077(14)

_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
Cl1 C1 1.544(6) . ?
F2 C2 1.351(4) . ?
C1 C2 1.364(5) 6 ?
C1 C2 1.364(5) . ?
C2 C2 1.370(9) 2 ?

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
C2 C1 Cl1 119.8(3) 6 . ?
C2 C1 Cl1 119.8(3) . . ?
C2 C1 C2 120.3(5) 6 . ?
F2 C2 C1 120.4(4) . . ?
F2 C2 C2 119.8(2) . 2 ?
C1 C2 C2 119.8(3) . 2 ?

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
Cl1 C1 C2 F2 -2.4(6) . . . . ?
Cl1 C1 C2 C2 179.3(4) . . . 2 ?
C2 C1 C2 F2 178.5(3) 6 . . . ?
C2 C1 C2 C2 0.1(8) 6 . . 2 ?

_shelx_res_file                  
;
    exp_2989.res created by SHELXL-2014/7

TITL exp_2989_a.res in C2/m
REM Old TITL exp_2989 in C2/m
REM SHELXT solution in C2/m
REM R1 0.244, Rweak 0.100, Alpha 0.073, Orientation as input
REM Formula found by SHELXT: C3 F2 Cl
CELL 1.54184 9.1116 7.7713 4.8027 90 95.977 90
ZERR 2 0.0006 0.0006 0.0004 0 0.007 0
LATT 7
SYMM -X,+Y,-Z
SFAC C Cl F
UNIT 12 2 10
EADP Cl1 F1
EXYZ Cl1 F1

L.S. 10
PLAN  5
TEMP 173
CONF
list 4
fmap 2 53
acta
MORE -1
OMIT 0 2 0
OMIT 1 1 5
REM <olex2.extras>
REM <HklSrc "%.\\exp_2989.hkl">
REM </olex2.extras>

WGHT    0.080100    0.473900
EXTI    0.092541
FVAR       2.53280
CL1   2    0.229203    0.000000   -0.378308    10.25000    0.08753    0.15595 =
         0.08105    0.00000    0.02654    0.00000
F1    3    0.229203    0.000000   -0.378308    10.25000    0.08753    0.15595 =
         0.08105    0.00000    0.02654    0.00000
F2    3    0.103797   -0.303133   -0.182917    11.00000    0.09660    0.07876 =
         0.14942   -0.02897   -0.00640    0.02407
C1    1    0.106797    0.000000   -0.178886    10.50000    0.05490    0.09073 =
         0.07306    0.00000    0.00333    0.00000
C2    1    0.053698   -0.152268   -0.089737    11.00000    0.06587    0.06712 =
         0.08916   -0.00946   -0.00606    0.00769
HKLF 4

REM  exp_2989_a.res in C2/m
REM R1 =  0.0694 for     323 Fo > 4sig(Fo)  and  0.0725 for all     359 data
REM     32 parameters refined using      0 restraints

END

WGHT      0.0804      0.4592

REM Highest difference peak  0.201,  deepest hole -0.332,  1-sigma level  0.055
Q1    1   0.1813 -0.1083 -0.3311  11.00000  0.05    0.20
Q2    1   0.1621 -0.2237 -0.2582  11.00000  0.05    0.19
Q3    1   0.1243  0.0000 -0.5019  10.50000  0.05    0.17
Q4    1   0.0000 -0.1379  0.0000  10.50000  0.05    0.15
Q5    1   0.1008 -0.3642 -0.2698  11.00000  0.05    0.14
;
_shelx_res_checksum              55627
_olex2_date_sample_data_collection 2021-12-08
_olex2_exptl_crystal_mounting_method '0.3mm X-ray capillary'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 4.464
_oxdiff_exptl_absorpt_empirical_full_min 0.392
