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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_100K
_database_code_depnum_ccdc_archive 'CCDC 2082045'
loop_
_audit_author_name
_audit_author_address
'Hans-Georg Stammler'
;Bielefeld University
Germany
;
_audit_update_record             
;
2021-05-06 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
# was jasc33_2_100_00_twin1_hklf4
_audit_creation_date             2017-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 F4 I N, C7 H8'
_chemical_formula_sum            'C12 H8 F4 I N'
_chemical_formula_weight         369.09
_chemical_melting_point          287
_chemical_oxdiff_formula         'C11 H5 F5 I N'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   7.4116(3)
_cell_length_b                   7.88224(9)
_cell_length_c                   10.6922(2)
_cell_angle_alpha                92.9070(14)
_cell_angle_beta                 94.961(2)
_cell_angle_gamma                94.097(2)
_cell_volume                     619.69(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    32146
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      36.6110
_cell_measurement_theta_min      3.1250
_cell_oxdiff_angle_alpha         92.9070(14)
_cell_oxdiff_angle_beta          94.961(2)
_cell_oxdiff_angle_gamma         94.097(2)
_cell_oxdiff_length_a            7.4116(2)
_cell_oxdiff_length_b            7.88224(9)
_cell_oxdiff_length_c            10.6922(2)
_cell_oxdiff_measurement_reflns_used 32146
_cell_oxdiff_volume              619.69(3)
_shelx_estimated_absorpt_T_max   0.458
_shelx_estimated_absorpt_T_min   0.292
_exptl_absorpt_coefficient_mu    2.614
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.107
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.15e (Rigaku Oxford Diffraction, 2015)
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_primary    colourless
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cylindrically
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.2951
8 0 8 0.1950
-8 0 -8 0.1950
11 -1 -1 0.1885
0 -1 0 0.2951
-11 1 1 0.1885
-9 1 10 0.1983
-4 0 -13 0.1967
4 0 13 0.1967
10 0 -7 0.1869
-10 0 7 0.1869
-6 0 13 0.1770
6 0 -13 0.1770
0 0 15 0.1770
0 0 -15 0.1770
7 -1 11 0.1787
-7 0 -11 0.1951
9 -1 -10 0.1983

_exptl_crystal_size_max          0.624
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.354
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
-0.0017 0.9949 0.0011 0.0030 0.0020 0.0898
7.9838 -0.0285 7.9813 0.4317 0.8715 0.0519
-7.9838 0.0285 -7.9813 -0.4317 -0.8715 -0.0519
10.9163 -1.0398 -0.8739 -0.1820 1.0288 -0.0360
0.0017 -0.9949 -0.0011 -0.0030 -0.0020 -0.0898
-10.9163 1.0398 0.8739 0.1820 -1.0288 0.0360
-8.8836 1.0359 9.7801 0.7406 -0.7131 0.0592
-4.0392 0.0100 -12.8760 -0.7953 -0.5615 -0.0390
4.0392 -0.0100 12.8760 0.7953 0.5615 0.0390
9.8904 -0.0436 -6.8068 -0.5549 0.8520 0.0400
-9.8904 0.0436 6.8068 0.5549 -0.8520 -0.0400
-5.8880 0.0303 12.7720 0.8995 -0.3883 -0.0112
5.8880 -0.0303 -12.7720 -0.8995 0.3883 0.0112
0.0788 0.0070 14.8089 0.9658 0.2095 0.0219
-0.0788 -0.0070 -14.8089 -0.9658 -0.2095 -0.0219
7.0085 -1.0180 10.9316 0.6323 0.8164 -0.0386
-7.0068 0.0231 -10.9327 -0.6353 -0.8185 -0.0512
8.8836 -1.0359 -9.7801 -0.7406 0.7131 -0.0592

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            68657
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.838
_diffrn_reflns_theta_min         2.595
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0951
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00 105.00   1.00   16.00    --   35.84  77.00-120.00   98
  2  ω     17.00 104.00   1.00   16.00    --   35.84  57.00  30.00   87
  3  ω     35.00 110.00   1.00   16.00    --   35.84 178.00-120.00   75
  4  ω     -4.00  22.00   1.00   16.00    --   35.84  97.00 -50.16   26
  5  ω     17.00 104.00   1.00   16.00    --   35.84  57.00 -30.00   87
  6  ω     35.00 110.00   1.00   16.00    --   35.84 178.00 -60.00   75
  7  ω     -2.00  25.00   1.00   16.00    --   35.84  95.00-175.00   27
  8  ω     14.00 106.00   1.00   16.00    --   35.84  38.00-120.00   92
  9  ω     35.00 110.00   1.00   16.00    --   35.84 178.00  60.00   75
 10  ω    -20.00  76.00   1.00   16.00    --   35.84 -99.00 120.00   96
 11  ω      7.00 105.00   1.00   16.00    --   35.84  77.00  60.00   98
 12  ω      7.00 105.00   1.00   16.00    --   35.84  77.00 120.00   98
 13  ω     34.00 111.00   1.00   16.00    --   35.84-178.00 120.00   77
 14  ω    -20.00  76.00   1.00   16.00    --   35.84 -99.00 -60.00   96
 15  ω    -33.00  54.00   1.00   16.00    --   35.84 -57.00   0.00   87
 16  ω     34.00 111.00   1.00   16.00    --   35.84-178.00 -30.00   77
 17  ω     17.00 104.00   1.00   16.00    --   35.84  57.00  60.00   87
 18  ω     17.00 104.00   1.00   16.00    --   35.84  57.00 150.00   87
 19  ω     -2.00 108.00   1.00   16.00    --   35.84  19.00  30.00  110
 20  ω     17.00 104.00   1.00   16.00    --   35.84  57.00-120.00   87
 21  ω     17.00 104.00   1.00   16.00    --   35.84  57.00 120.00   87
 22  ω     17.00 104.00   1.00   16.00    --   35.84  57.00 -90.00   87
 23  ω    -35.00 107.00   1.00   16.00    --   35.84   0.00-180.00  142
 24  ω    -35.00 107.00   1.00   16.00    --   35.84   0.00-150.00  142
 25  ω    -35.00 107.00   1.00   16.00    --   35.84   0.00-120.00  142
 26  ω    -35.00 107.00   1.00   16.00    --   35.84   0.00 -90.00  142
 27  ω     14.00 106.00   1.00   16.00    --   35.84  38.00  30.00   92
 28  ω    -35.00 107.00   1.00   16.00    --   35.84   0.00 -30.00  142
 29  ω    -35.00 107.00   1.00   16.00    --   35.84   0.00 -60.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0111710000
_diffrn_orient_matrix_UB_12      0.0028910000
_diffrn_orient_matrix_UB_13      0.0652728000
_diffrn_orient_matrix_UB_21      0.0955384000
_diffrn_orient_matrix_UB_22      0.0021664000
_diffrn_orient_matrix_UB_23      0.0136364000
_diffrn_orient_matrix_UB_31      0.0054139000
_diffrn_orient_matrix_UB_32      0.0902937000
_diffrn_orient_matrix_UB_33      0.0014047000
_diffrn_oxdiff_ac3_digest_frames 
;
0148f493577466de9410b867f057a371d90276453df
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01c8878af9b9efdb0197887cfc9e152964e7cc
;
_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          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10641
_reflns_number_total             10787
_reflns_special_details          
;
 _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 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.798
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         10787
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0173
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.1180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0477
_refine_special_details          
'Just below the m.p. of the mixture (287 K) a crystal seed was manuallly in-situ grown at 286 K and chilled to 200 K with 20 K/h and to 100 K with 50 K/h. The crystal undergoes a phase transition at ca. 232 K from a monoclic phase to this triclinic phase. Also if the cell parameters are changing considerably, the crystal was not destroyed, but forms a twin with the two domains rotated by 180&deg around the former monoclinic axis with ratio 1:1. All hydrogen atomes were taken into account using a riding model. The methyl group was refined with idealized disordered hydrogen atoms, i.e. with two positions rotated from each other by 60&deg , their ratio was found to be 72:28.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
3.b Disordered Me refined as rotating group:
 C12(H12A,H12B,H12C,H12D,H12E,H12F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 1.00023(2) 0.28453(2) 0.75279(2) 0.01750(2) Uani 1 1 d . . . . .
F1 F 0.85434(12) 0.88316(12) 0.56150(8) 0.02423(15) Uani 1 1 d . . . . .
F2 F 0.83844(11) 0.53908(11) 0.55242(7) 0.02058(13) Uani 1 1 d . . . . .
F3 F 1.16469(10) 0.58544(11) 0.95537(7) 0.02002(13) Uani 1 1 d . . . . .
F4 F 1.15992(12) 0.92727(11) 0.94593(8) 0.02365(15) Uani 1 1 d . . . . .
N1 N 1.00749(14) 0.90238(12) 0.75394(10) 0.01718(15) Uani 1 1 d . . . . .
C1 C 0.92956(15) 0.80410(16) 0.65794(10) 0.01656(17) Uani 1 1 d . . . . .
C2 C 0.92237(14) 0.62844(14) 0.65320(10) 0.01454(16) Uani 1 1 d . . . . .
C3 C 1.00178(14) 0.54760(13) 0.75374(10) 0.01368(14) Uani 1 1 d . . . . .
C4 C 1.08436(14) 0.65166(14) 0.85473(10) 0.01427(16) Uani 1 1 d . . . . .
C5 C 1.08223(15) 0.82609(15) 0.84972(11) 0.01619(17) Uani 1 1 d . . . . .
C6 C 0.51492(15) 0.13919(17) 0.27680(11) 0.01957(19) Uani 1 1 d . . . . .
C7 C 0.56367(16) 0.28588(18) 0.35437(11) 0.02088(19) Uani 1 1 d . . . . .
H7 H 0.616757 0.275616 0.437489 0.025 Uiso 1 1 calc R . . . .
C8 C 0.53602(17) 0.44645(19) 0.31235(13) 0.0239(2) Uani 1 1 d . . . . .
H8 H 0.570420 0.544705 0.366655 0.029 Uiso 1 1 calc R . . . .
C9 C 0.45820(18) 0.4642(2) 0.19111(14) 0.0262(2) Uani 1 1 d . . . . .
H9 H 0.439104 0.574117 0.162235 0.031 Uiso 1 1 calc R . . . .
C10 C 0.40859(17) 0.3192(2) 0.11253(12) 0.0262(2) Uani 1 1 d . . . . .
H10 H 0.355095 0.330118 0.029617 0.031 Uiso 1 1 calc R . . . .
C11 C 0.43670(16) 0.1591(2) 0.15443(12) 0.0237(2) Uani 1 1 d . . . . .
H11 H 0.402628 0.061210 0.099678 0.028 Uiso 1 1 calc R . . . .
C12 C 0.5421(2) -0.0355(2) 0.32125(16) 0.0304(3) Uani 1 1 d . . . . .
H12A H 0.492064 -0.046909 0.402545 0.037 Uiso 0.28(2) 1 calc GR . P . .
H12B H 0.672232 -0.052351 0.330502 0.037 Uiso 0.28(2) 1 calc GR . P . .
H12C H 0.479878 -0.121237 0.259728 0.037 Uiso 0.28(2) 1 calc GR . P . .
H12D H 0.604052 -0.100089 0.259305 0.037 Uiso 0.72(2) 1 calc GR . P . .
H12E H 0.423884 -0.094647 0.331348 0.037 Uiso 0.72(2) 1 calc GR . P . .
H12F H 0.616238 -0.025761 0.402122 0.037 Uiso 0.72(2) 1 calc GR . P . .


_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
I1 C3 2.0723(10) . ?
F1 C1 1.3334(13) . ?
F2 C2 1.3374(12) . ?
F3 C4 1.3325(12) . ?
F4 C5 1.3322(13) . ?
N1 C1 1.3192(15) . ?
N1 C5 1.3150(15) . ?
C1 C2 1.3800(17) . ?
C2 C3 1.3863(15) . ?
C3 C4 1.3919(14) . ?
C4 C5 1.3798(17) . ?
C6 C7 1.3952(18) . ?
C6 C11 1.4054(17) . ?
C6 C12 1.501(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.3906(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12D 0.9800 . ?
C12 H12E 0.9800 . ?
C12 H12F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 117.10(10) . . ?
F1 C1 C2 119.70(10) . . ?
N1 C1 F1 116.45(11) . . ?
N1 C1 C2 123.85(10) . . ?
F2 C2 C1 119.67(10) . . ?
F2 C2 C3 121.12(10) . . ?
C1 C2 C3 119.21(9) . . ?
C2 C3 I1 121.58(8) . . ?
C2 C3 C4 116.80(10) . . ?
C4 C3 I1 121.61(8) . . ?
F3 C4 C3 121.08(10) . . ?
F3 C4 C5 119.88(9) . . ?
C5 C4 C3 119.04(10) . . ?
F4 C5 C4 119.71(10) . . ?
N1 C5 F4 116.29(10) . . ?
N1 C5 C4 124.00(10) . . ?
C7 C6 C11 117.88(12) . . ?
C7 C6 C12 121.86(12) . . ?
C11 C6 C12 120.25(13) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.20(12) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.30(13) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.23(14) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.42(12) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.5 . . ?
C10 C11 C6 120.97(13) . . ?
C10 C11 H11 119.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
C6 C12 H12D 109.5 . . ?
C6 C12 H12E 109.5 . . ?
C6 C12 H12F 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12A C12 H12D 141.1 . . ?
H12A C12 H12E 56.3 . . ?
H12A C12 H12F 56.3 . . ?
H12B C12 H12C 109.5 . . ?
H12B C12 H12D 56.3 . . ?
H12B C12 H12E 141.1 . . ?
H12B C12 H12F 56.3 . . ?
H12C C12 H12D 56.3 . . ?
H12C C12 H12E 56.3 . . ?
H12C C12 H12F 141.1 . . ?
H12D C12 H12E 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?

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
I1 C3 C4 F3 -0.49(14) . . . . ?
I1 C3 C4 C5 179.55(8) . . . . ?
F1 C1 C2 F2 -0.66(15) . . . . ?
F1 C1 C2 C3 179.69(10) . . . . ?
F2 C2 C3 I1 1.28(14) . . . . ?
F2 C2 C3 C4 -179.41(9) . . . . ?
F3 C4 C5 F4 -0.30(15) . . . . ?
F3 C4 C5 N1 179.45(11) . . . . ?
N1 C1 C2 F2 179.20(11) . . . . ?
N1 C1 C2 C3 -0.44(17) . . . . ?
C1 N1 C5 F4 -179.86(11) . . . . ?
C1 N1 C5 C4 0.39(16) . . . . ?
C1 C2 C3 I1 -179.07(8) . . . . ?
C1 C2 C3 C4 0.23(15) . . . . ?
C2 C3 C4 F3 -179.79(9) . . . . ?
C2 C3 C4 C5 0.24(15) . . . . ?
C3 C4 C5 F4 179.67(10) . . . . ?
C3 C4 C5 N1 -0.59(17) . . . . ?
C5 N1 C1 F1 180.00(11) . . . . ?
C5 N1 C1 C2 0.13(16) . . . . ?
C6 C7 C8 C9 0.12(19) . . . . ?
C7 C6 C11 C10 -0.17(18) . . . . ?
C7 C8 C9 C10 -0.05(19) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C6 0.2(2) . . . . ?
C11 C6 C7 C8 -0.01(17) . . . . ?
C12 C6 C7 C8 -179.36(12) . . . . ?
C12 C6 C11 C10 179.18(13) . . . . ?

_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 8.650
_oxdiff_exptl_absorpt_empirical_full_min 0.656
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5036 32598 23378 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4964 32613 23378 nmt -1.0001 -0.1348 0.0001 0.0002 1.0000 -0.0001 0.0001
-0.1371 -0.9998

_twin_special_details            
;
Component 2 rotated by -179.9950° 
 around [-0.07 1.00 -0.07] (reciprocal) or [0.00 1.00 0.00] (direct)
;
####################################################################### 
# 
# 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_1_232K
_database_code_depnum_ccdc_archive 'CCDC 2082044'
loop_
_audit_author_name
_audit_author_address
'Hans-Georg Stammler'
;Bielefeld University
Germany
;
_audit_update_record             
;
2021-10-13 deposited with the CCDC.	2021-12-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_1_232K              
;
PROBLEM: Hirshfeld Test Diff for    C1       --C2       .        7.4 s.u.
RESPONSE: Both atoms were checked to be carbon atoms. All thermal 
parameters are large because of the high temperature. 
;
# Added during the CSD deposition process: Thursday 06 May 2021 08:23 AM
# end Validation Reply Form

# was jasc33_c_3_232_00
_audit_creation_date             2017-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 F4 I N, 1(C7 H8)'
_chemical_formula_sum            'C12 H8 F4 I N'
_chemical_formula_weight         369.09
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c12 h8 F4 N I'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   7.4279(2)
_cell_length_b                   7.9778(2)
_cell_length_c                   11.0063(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.478(3)
_cell_angle_gamma                90
_cell_volume                     646.67(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7071
_cell_measurement_temperature    232.0(1)
_cell_measurement_theta_max      31.6980
_cell_measurement_theta_min      2.5410
_shelx_estimated_absorpt_T_max   0.471
_shelx_estimated_absorpt_T_min   0.304
_exptl_absorpt_coefficient_mu    2.505
_exptl_absorpt_correction_T_max  0.4345
_exptl_absorpt_correction_T_min  0.1746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0892 before and 0.0365 after correction. The Ratio of minimum to maximum transmission is 0.4018. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cylindrically
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.2951
11 -1 -2 0.1885
9 -1 -11 0.1983
-7 0 -11 0.1951
0 0 -15 0.1770
0 0 15 0.1770
6 0 -14 0.1770
-6 0 14 0.1770
10 0 -8 0.1869
4 0 13 0.1967
-4 0 -13 0.1967
0 -1 0 0.2951
-9 1 11 0.1983
-11 1 2 0.1885
8 0 8 0.1950
-10 0 8 0.1869
-8 0 -8 0.1950
7 -1 11 0.1787

_exptl_crystal_size_max          0.624
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.354
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
0.0589 1.0083 0.0436 0.0030 0.0020 0.0898
10.9106 -0.9614 -1.7971 -0.1820 1.0288 -0.0360
8.7901 -1.0900 -10.7582 -0.7406 0.7131 -0.0592
-7.1404 -0.1819 -10.6449 -0.6353 -0.8185 -0.0512
-0.2060 -0.1961 -15.1603 -0.9658 -0.2095 -0.0219
0.2060 0.1961 15.1603 0.9658 0.2095 0.0219
5.8124 -0.1373 -13.5441 -0.8995 0.3883 0.0112
-5.8124 0.1373 13.5441 0.8995 -0.3883 -0.0112
9.8887 -0.0370 -7.7501 -0.5549 0.8520 0.0400
4.1724 0.1917 12.8688 0.7953 0.5615 0.0390
-4.1724 -0.1917 -12.8688 -0.7953 -0.5615 -0.0390
-0.0589 -1.0083 -0.0436 -0.0030 -0.0020 -0.0898
-8.7901 1.0900 10.7582 0.7406 -0.7131 0.0592
-10.9106 0.9614 1.7971 0.1820 -1.0288 0.0360
8.0977 0.1482 7.5453 0.4317 0.8715 0.0519
-9.8887 0.0370 7.7501 0.5549 -0.8520 -0.0400
-8.0977 -0.1482 -7.5453 -0.4317 -0.8715 -0.0519
7.0815 -0.8264 10.6013 0.6323 0.8164 -0.0386

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11846
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_min         2.553
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      232.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0951
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  79.00   1.00    8.00    --   24.87   0.00-120.00  124
  2  ω    -38.00  45.00   1.00    8.00    --   24.87 -38.00-180.00   83
  3  ω     -4.00  91.00   1.00    8.00    --   24.87  77.00  30.00   95
  4  ω     30.00  85.00   1.00    8.00    --   24.87-134.00 158.00   55
  5  ω     -4.00  91.00   1.00    8.00    --   24.87  77.00-150.00   95
  6  ω     32.00  87.00   1.00    8.00    --   24.87-136.00 -20.00   55
  7  ω      6.00  54.00   1.00    8.00    --   24.87  57.00 -30.00   48
  8  ω      6.00  54.00   1.00    8.00    --   24.87  57.00 150.00   48
  9  ω     36.00  99.00   1.00    8.00    --   24.87 178.00 120.00   63
 10  ω    -44.00  86.00   1.00    8.00    --   24.87   0.00  30.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0061277000
_diffrn_orient_matrix_UB_12      0.0005439000
_diffrn_orient_matrix_UB_13      0.0637794000
_diffrn_orient_matrix_UB_21      0.0959931000
_diffrn_orient_matrix_UB_22      -0.0041584000
_diffrn_orient_matrix_UB_23      0.0125676000
_diffrn_orient_matrix_UB_31      0.0045637000
_diffrn_orient_matrix_UB_32      0.0888143000
_diffrn_orient_matrix_UB_33      0.0002314000
_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'
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3385
_reflns_number_total             3768
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_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 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.15e (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3768
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0190
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0171P)²+0.0827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0442
_refine_special_details          
'Grown as described for 2_100K, afterwards warming up to the temperature of phase transition at 232K. The toluene shows a diordering with ratio of 65:35. Viewing along the a axis the transition to the triclinic phase is forshaded by this disorder. All carbon atoms of the toluene molecule were restrained to have the same Uij components as their neighbouring atoms, their benzene rings were constrained to idealized hexagons. The crystal is a 1:1 inversion twin.'
_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
 C6A-C12A \\sim C6B-C12B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C6A \\sim C7A \\sim H7A \\sim C8A \\sim H8A \\sim C9A \\sim H9A \\sim C10A
\\sim H10A \\sim C11A \\sim H11A \\sim C12A \\sim H12A \\sim H12B \\sim H12C
\\sim C6B \\sim C7B \\sim H7B \\sim C8B \\sim H8B \\sim C9B \\sim H9B \\sim
C10B \\sim H10B \\sim C11B \\sim H11B \\sim C12B \\sim H12D \\sim H12E \\sim
H12F: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(C8B)=Sof(H8B)=Sof(C7B)=Sof(H7B)=Sof(C6B)=Sof(C11B)=Sof(H11B)=Sof(C10B)=
 Sof(H10B)=Sof(C9B)=Sof(H9B)=Sof(C12B)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(C10A)=Sof(H10A)=Sof(C9A)=Sof(H9A)=Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=
 Sof(C6A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C9A(H9A), C8A(H8A), C7A(H7A), C11A(H11A), C8B(H8B), C7B(H7B),
 C11B(H11B), C10B(H10B), C9B(H9B)
5.b Fitted hexagon refined as free rotating group:
 C10A(C9A,C8A,C7A,C6A,C11A), C8B(C7B,C6B,C11B,C10B,C9B)
5.c Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.5575(4) 0.68344(2) 0.6143(2) 0.05847(8) Uani 1 1 d . . . . .
F1 F 0.4028(13) 0.0835(10) 0.4189(9) 0.087(2) Uani 1 1 d . . . . .
F2 F 0.3974(10) 0.4124(9) 0.4138(5) 0.072(2) Uani 1 1 d . . . . .
F3 F 0.7156(9) 0.4080(7) 0.8127(6) 0.0622(17) Uani 1 1 d . . . . .
F4 F 0.7071(13) 0.0638(8) 0.8001(9) 0.0713(18) Uani 1 1 d . . . . .
N1 N 0.5508(19) 0.0775(3) 0.6065(14) 0.0554(14) Uani 1 1 d . . . . .
C1 C 0.4811(17) 0.1684(13) 0.5228(13) 0.064(3) Uani 1 1 d . . . . .
C2 C 0.4788(14) 0.3381(10) 0.5160(10) 0.048(2) Uani 1 1 d . . . . .
C3 C 0.5594(19) 0.4228(3) 0.6158(12) 0.0432(6) Uani 1 1 d . . . . .
C4 C 0.6370(13) 0.3268(9) 0.7143(7) 0.046(2) Uani 1 1 d . . . . .
C5 C 0.6321(14) 0.1578(9) 0.7117(11) 0.0453(19) Uani 1 1 d . . . . .
C10A C 0.1012(18) 0.4186(12) 0.6713(11) 0.061(4) Uani 0.652(17) 1 d . U P A 1
H10A H 0.139094 0.509256 0.722926 0.074 Uiso 0.652(17) 1 calc R U P A 1
C9A C 0.023(2) 0.4478(8) 0.5514(12) 0.062(3) Uani 0.652(17) 1 d G U P A 1
H9A H 0.008181 0.558202 0.521998 0.074 Uiso 0.652(17) 1 calc R U P A 1
C8A C -0.033(2) 0.3137(13) 0.4751(8) 0.062(3) Uani 0.652(17) 1 d G U P A 1
H8A H -0.085698 0.333491 0.394006 0.074 Uiso 0.652(17) 1 calc R U P A 1
C7A C -0.011(2) 0.1505(10) 0.5186(11) 0.064(4) Uani 0.652(17) 1 d G U P A 1
H7A H -0.048667 0.059833 0.466938 0.077 Uiso 0.652(17) 1 calc R U P A 1
C6A C 0.067(2) 0.1213(9) 0.6384(12) 0.055(3) Uani 0.652(17) 1 d DG U P A 1
C11A C 0.1233(14) 0.2553(15) 0.7148(8) 0.056(3) Uani 0.652(17) 1 d G U P A 1
H11A H 0.176126 0.235594 0.795860 0.067 Uiso 0.652(17) 1 calc R U P A 1
C12A C 0.101(3) -0.0557(18) 0.666(2) 0.105(7) Uani 0.652(17) 1 d D U P A 1
H12A H 0.107613 -0.116207 0.589857 0.157 Uiso 0.652(17) 1 calc GR U P A 1
H12B H 0.002371 -0.100651 0.705618 0.157 Uiso 0.652(17) 1 calc GR U P A 1
H12C H 0.214363 -0.067868 0.719160 0.157 Uiso 0.652(17) 1 calc GR U P A 1
C8B C -0.007(3) 0.3888(19) 0.5232(17) 0.063(6) Uani 0.348(17) 1 d . U P A 2
H8B H -0.048588 0.463475 0.459592 0.076 Uiso 0.348(17) 1 calc R U P A 2
C7B C -0.015(3) 0.217(2) 0.5025(13) 0.063(6) Uani 0.348(17) 1 d G U P A 2
H7B H -0.062292 0.175362 0.424936 0.076 Uiso 0.348(17) 1 calc R U P A 2
C6B C 0.046(3) 0.1066(13) 0.5965(15) 0.043(5) Uani 0.348(17) 1 d DG U P A 2
C11B C 0.116(3) 0.1681(15) 0.7112(13) 0.038(4) Uani 0.348(17) 1 d G U P A 2
H11B H 0.157868 0.093402 0.774749 0.046 Uiso 0.348(17) 1 calc R U P A 2
C10B C 0.124(3) 0.3399(17) 0.7319(16) 0.068(6) Uani 0.348(17) 1 d G U P A 2
H10B H 0.171573 0.381513 0.809408 0.082 Uiso 0.348(17) 1 calc R U P A 2
C9B C 0.063(4) 0.4503(12) 0.638(2) 0.063(6) Uani 0.348(17) 1 d G U P A 2
H9B H 0.068347 0.566552 0.651831 0.075 Uiso 0.348(17) 1 calc R U P A 2
C12B C 0.039(4) -0.071(2) 0.548(3) 0.066(6) Uani 0.348(17) 1 d D U P A 2
H12D H 0.024422 -0.068760 0.458660 0.099 Uiso 0.348(17) 1 calc GR U P A 2
H12E H -0.062538 -0.129884 0.574972 0.099 Uiso 0.348(17) 1 calc GR U P A 2
H12F H 0.151177 -0.128926 0.577573 0.099 Uiso 0.348(17) 1 calc GR U 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
I1 C3 2.079(3) . ?
F1 C1 1.389(15) . ?
F2 C2 1.344(13) . ?
F3 C4 1.330(11) . ?
F4 C5 1.296(13) . ?
N1 C1 1.233(19) . ?
N1 C5 1.390(17) . ?
C1 C2 1.356(9) . ?
C2 C3 1.360(16) . ?
C3 C4 1.390(15) . ?
C4 C5 1.349(7) . ?
C10A H10A 0.9400 . ?
C10A C9A 1.3900 . ?
C10A C11A 1.3900 . ?
C9A H9A 0.9400 . ?
C9A C8A 1.3900 . ?
C8A H8A 0.9400 . ?
C8A C7A 1.3900 . ?
C7A H7A 0.9400 . ?
C7A C6A 1.3900 . ?
C6A C11A 1.3900 . ?
C6A C12A 1.457(13) . ?
C11A H11A 0.9400 . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C12A H12C 0.9700 . ?
C8B H8B 0.9400 . ?
C8B C7B 1.3900 . ?
C8B C9B 1.3900 . ?
C7B H7B 0.9400 . ?
C7B C6B 1.3900 . ?
C6B C11B 1.3900 . ?
C6B C12B 1.516(17) . ?
C11B H11B 0.9400 . ?
C11B C10B 1.3900 . ?
C10B H10B 0.9400 . ?
C10B C9B 1.3900 . ?
C9B H9B 0.9400 . ?
C12B H12D 0.9700 . ?
C12B H12E 0.9700 . ?
C12B H12F 0.9700 . ?

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
C1 N1 C5 116.5(3) . . ?
N1 C1 F1 114.7(9) . . ?
N1 C1 C2 129.0(12) . . ?
C2 C1 F1 116.2(13) . . ?
F2 C2 C1 119.1(11) . . ?
F2 C2 C3 124.1(7) . . ?
C1 C2 C3 116.8(11) . . ?
C2 C3 I1 119.2(8) . . ?
C2 C3 C4 116.8(3) . . ?
C4 C3 I1 124.0(7) . . ?
F3 C4 C3 117.4(6) . . ?
F3 C4 C5 120.8(8) . . ?
C5 C4 C3 121.8(9) . . ?
F4 C5 N1 117.2(7) . . ?
F4 C5 C4 123.6(10) . . ?
C4 C5 N1 119.1(9) . . ?
C9A C10A H10A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C6A C7A C8A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C7A C6A C11A 120.0 . . ?
C7A C6A C12A 113.3(13) . . ?
C11A C6A C12A 126.3(13) . . ?
C10A C11A H11A 120.0 . . ?
C6A C11A C10A 120.0 . . ?
C6A C11A H11A 120.0 . . ?
C6A C12A H12A 109.5 . . ?
C6A C12A H12B 109.5 . . ?
C6A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C7B C8B H8B 120.0 . . ?
C7B C8B C9B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C6B C7B C8B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C7B C6B C11B 120.0 . . ?
C7B C6B C12B 109.6(15) . . ?
C11B C6B C12B 130.2(16) . . ?
C6B C11B H11B 120.0 . . ?
C10B C11B C6B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C11B C10B C9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C6B C12B H12D 109.5 . . ?
C6B C12B H12E 109.5 . . ?
C6B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?

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
I1 C3 C4 F3 -0.5(16) . . . . ?
I1 C3 C4 C5 178.9(9) . . . . ?
F1 C1 C2 F2 2.4(19) . . . . ?
F1 C1 C2 C3 -178.2(12) . . . . ?
F2 C2 C3 I1 0.5(17) . . . . ?
F2 C2 C3 C4 179.8(7) . . . . ?
F3 C4 C5 F4 -2.6(19) . . . . ?
F3 C4 C5 N1 -179.1(12) . . . . ?
N1 C1 C2 F2 178.5(16) . . . . ?
N1 C1 C2 C3 -2(3) . . . . ?
C1 N1 C5 F4 -179.5(9) . . . . ?
C1 N1 C5 C4 -3(3) . . . . ?
C1 C2 C3 I1 -178.8(10) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 F3 -179.7(7) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 F4 178.0(12) . . . . ?
C3 C4 C5 N1 1.5(19) . . . . ?
C5 N1 C1 F1 179.4(8) . . . . ?
C5 N1 C1 C2 3(3) . . . . ?
C10A C9A C8A C7A 0.0 . . . . ?
C9A C10A C11A C6A 0.0 . . . . ?
C9A C8A C7A C6A 0.0 . . . . ?
C8A C7A C6A C11A 0.0 . . . . ?
C8A C7A C6A C12A -173.1(15) . . . . ?
C7A C6A C11A C10A 0.0 . . . . ?
C11A C10A C9A C8A 0.0 . . . . ?
C12A C6A C11A C10A 172.1(18) . . . . ?
C8B C7B C6B C11B 0.0 . . . . ?
C8B C7B C6B C12B -175(2) . . . . ?
C7B C8B C9B C10B 0.0 . . . . ?
C7B C6B C11B C10B 0.0 . . . . ?
C6B C11B C10B C9B 0.0 . . . . ?
C11B C10B C9B C8B 0.0 . . . . ?
C9B C8B C7B C6B 0.0 . . . . ?
C12B C6B C11B C10B 173(3) . . . . ?

_olex2_date_sample_data_collection 2017-10-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details ?
_oxdiff_exptl_absorpt_empirical_full_max 4.544
_oxdiff_exptl_absorpt_empirical_full_min 0.666
