# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 2291313'
loop_
_audit_author_name
_audit_author_address
'Blanka Klepetarova'
;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 
Czech Republic
;
_audit_update_record             
;
2023-08-28 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.6612(3)
_cell_length_b                   8.6533(3)
_cell_length_c                   8.7731(3)
_cell_angle_alpha                107.8102(12)
_cell_angle_beta                 94.3444(13)
_cell_angle_gamma                95.6658(13)
_cell_volume                     547.57(3)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2
_chemical_name_systematic        
'1-(perfluoroethyl)-1H-indole-2-carboxylic acid'
_chemical_formula_moiety         'C11 H6 F5 N O2'

# Given Formula = C11 H6 F5 N1 O2 
# Dc =      1.69 Fooo =    280.00 Mu =     15.57 M =    279.16
# Found Formula = C11 H6 F5 N1 O2 
# Dc =      1.69 FOOO =    280.00 Mu =     15.57 M =    279.16

_chemical_formula_sum            'C11 H6 F5 N O2'
_chemical_compound_source        .
_chemical_formula_weight         279.16


_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      5.3293
_cell_measurement_theta_max      68.1760
_cell_measurement_temperature    180

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.090
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_max          0.254

_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    1.557

# Sheldrick geometric approximatio 0.81 0.87 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Unknown
_diffrn_radiation_monochromator  Unknown
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .
_diffrn_reflns_number            15955
_diffrn_reflns_av_unetI/netI     0.054
_reflns_number_total             2004
_diffrn_reflns_av_R_equivalents  0.032
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2004 
# Theoretical number of reflections is about 4009 


_diffrn_reflns_theta_min         5.329
_diffrn_reflns_theta_max         68.214
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        66.850
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   3.05
_oxford_diffrn_Wilson_scale      7.52

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.54


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>2.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1887
_oxford_refine_ls_R_factor_ref   0.0438
_refine_ls_R_factor_all          0.0438
_refine_ls_wR_factor_ref         0.0555
_refine_ls_wR_factor_all         0.0555
_refine_ls_goodness_of_fit_ref   1.0102
_refine_ls_shift/su_max          0.0047659
_refine_ls_shift/su_mean         0.0008702


# Computed with I/sigma = -10 
_oxford_reflns_number_all        2004
_oxford_refine_ls_R_factor_all   0.0464
_oxford_refine_ls_wR_factor_all  0.0613

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1887
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_gt          0.0555


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method = Chebychev polynomial, (Carruthers & Watkin, 1979) 
 W = 1.0/[A[0]*T[0]'(X)+A[1]*T[1]'(X) ... +A[NP-1]*T[NP-1]'(X)] 
 0.298 0.393 0.123 0.970E-03 -0.156E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F 0.96102(18) 0.92451(16) 0.23118(16) 0.0479 1.0000 Uani . . . . . .
F2 F 0.85689(17) 0.83899(15) 0.41618(14) 0.0446 1.0000 Uani . . . . . .
F3 F 0.7359(2) 1.10815(16) 0.40117(18) 0.0668 1.0000 Uani . . . . . .
F4 F 0.5219(2) 0.9082(2) 0.3083(2) 0.0639 1.0000 Uani . . . . . .
O5 O 0.5766(2) 0.64867(17) 0.43089(16) 0.0396 1.0000 Uani . . . . . .
O6 O 0.5856(2) 0.38046(17) 0.32089(19) 0.0480 1.0000 Uani . . . . . .
F7 F 0.6548(2) 1.0037(2) 0.14423(19) 0.0665 1.0000 Uani . . . . . .
N8 N 0.7578(2) 0.69312(19) 0.1515(2) 0.0358 1.0000 Uani . . . . . .
C9 C 0.7057(3) 0.4180(2) 0.0477(2) 0.0335 1.0000 Uani . . . . . .
C10 C 0.8661(3) 0.7474(3) -0.0975(3) 0.0412 1.0000 Uani . . . . . .
C11 C 0.7729(3) 0.4790(2) -0.0721(2) 0.0322 1.0000 Uani . . . . . .
C12 C 0.8038(3) 0.6506(2) -0.0071(2) 0.0340 1.0000 Uani . . . . . .
C13 C 0.8134(3) 0.8506(3) 0.2698(3) 0.0400 1.0000 Uani . . . . . .
C14 C 0.6960(3) 0.5462(2) 0.1811(2) 0.0334 1.0000 Uani . . . . . .
C15 C 0.8089(3) 0.4025(3) -0.2302(2) 0.0379 1.0000 Uani . . . . . .
C16 C 0.6151(3) 0.5342(2) 0.3242(2) 0.0337 1.0000 Uani . . . . . .
C17 C 0.8985(3) 0.6683(3) -0.2527(3) 0.0445 1.0000 Uani . . . . . .
C18 C 0.8722(3) 0.4979(3) -0.3177(3) 0.0439 1.0000 Uani . . . . . .
C19 C 0.6765(4) 0.9707(3) 0.2820(3) 0.0478 1.0000 Uani . . . . . .
H91 H 0.6713 0.3082 0.0364 0.0390 1.0000 Uiso R . . . . .
H101 H 0.8848 0.8625 -0.0561 0.0486 1.0000 Uiso R . . . . .
H151 H 0.7902 0.2877 -0.2739 0.0449 1.0000 Uiso R . . . . .
H171 H 0.9403 0.7319 -0.3146 0.0530 1.0000 Uiso R . . . . .
H181 H 0.8964 0.4485 -0.4222 0.0534 1.0000 Uiso R . . . . .
H61 H 0.5403 0.3742 0.4022 0.0720 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       21(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.3947(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C13 . 1.361(2) yes
F2 . C13 . 1.339(2) yes
F3 . C19 . 1.332(3) yes
F4 . C19 . 1.319(3) yes
O5 . C16 . 1.215(2) yes
O6 . C16 . 1.318(2) yes
O6 . H61 . 0.831 no
F7 . C19 . 1.327(3) yes
N8 . C12 . 1.407(3) yes
N8 . C13 . 1.438(3) yes
N8 . C14 . 1.418(2) yes
C9 . C11 . 1.420(3) yes
C9 . C14 . 1.357(3) yes
C9 . H91 . 0.934 no
C10 . C12 . 1.395(3) yes
C10 . C17 . 1.378(3) yes
C10 . H101 . 0.942 no
C11 . C12 . 1.406(3) yes
C11 . C15 . 1.403(3) yes
C13 . C19 . 1.535(3) yes
C14 . C16 . 1.469(3) yes
C15 . C18 . 1.368(3) yes
C15 . H151 . 0.941 no
C17 . C18 . 1.396(3) yes
C17 . H171 . 0.935 no
C18 . H181 . 0.927 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 . O6 . H61 . 110.5 no
C12 . N8 . C13 . 123.39(17) yes
C12 . N8 . C14 . 107.54(16) yes
C13 . N8 . C14 . 126.86(16) yes
C11 . C9 . C14 . 108.75(17) yes
C11 . C9 . H91 . 125.9 no
C14 . C9 . H91 . 125.3 no
C12 . C10 . C17 . 117.4(2) yes
C12 . C10 . H101 . 122.2 no
C17 . C10 . H101 . 120.4 no
C9 . C11 . C12 . 107.44(17) yes
C9 . C11 . C15 . 132.90(18) yes
C12 . C11 . C15 . 119.66(18) yes
N8 . C12 . C11 . 107.51(17) yes
N8 . C12 . C10 . 131.09(19) yes
C11 . C12 . C10 . 121.39(19) yes
N8 . C13 . F1 . 110.41(17) yes
N8 . C13 . F2 . 112.17(17) yes
F1 . C13 . F2 . 105.76(17) yes
N8 . C13 . C19 . 113.60(19) yes
F1 . C13 . C19 . 105.49(17) yes
F2 . C13 . C19 . 108.91(18) yes
N8 . C14 . C9 . 108.76(17) yes
N8 . C14 . C16 . 126.00(17) yes
C9 . C14 . C16 . 124.89(18) yes
C11 . C15 . C18 . 118.7(2) yes
C11 . C15 . H151 . 120.1 no
C18 . C15 . H151 . 121.2 no
C14 . C16 . O6 . 110.84(17) yes
C14 . C16 . O5 . 125.37(18) yes
O6 . C16 . O5 . 123.78(18) yes
C10 . C17 . C18 . 121.8(2) yes
C10 . C17 . H171 . 118.2 no
C18 . C17 . H171 . 120.0 no
C17 . C18 . C15 . 121.0(2) yes
C17 . C18 . H181 . 119.6 no
C15 . C18 . H181 . 119.4 no
C13 . C19 . F3 . 108.7(2) yes
C13 . C19 . F7 . 109.14(19) yes
F3 . C19 . F7 . 109.47(19) yes
C13 . C19 . F4 . 111.56(18) yes
F3 . C19 . F4 . 110.1(2) yes
F7 . C19 . F4 . 107.9(2) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O6 . H61 . O5 2_666 175 0.83 1.82 2.653(3) yes


# looking for ARCHIVE-HKL.CIF 


# end of ARCHIVE-HKL.CIF 
