# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 2336080'
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             
;
2024-02-28 deposited with the CCDC.	2024-06-17 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. 
;


#--------------------------------------------------------------- 
# _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                   8.18502(15)
_cell_length_b                   13.51475(17)
_cell_length_c                   8.59865(14)
_cell_angle_alpha                90
_cell_angle_beta                 117.183(2)
_cell_angle_gamma                90
_cell_volume                     846.12(3)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

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'
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            4
_chemical_name_systematic        3-Fluoro-1-(trifluoromethyl)isoquinoline
_chemical_formula_moiety         'C10 H5 F4 N'

# Given Formula = C7.50 H3.75 F3 N0.75 
# Dc =      1.27 Fooo =    324.00 Mu =     10.88 M =    161.36
# Found Formula = C10 H5 F4 N1 
# Dc =      1.69 FOOO =    432.00 Mu =     14.50 M =    215.15

_chemical_formula_sum            'C10 H5 F4 N'
_chemical_compound_source        .
_chemical_formula_weight         215.15


_cell_measurement_reflns_used    7290
_cell_measurement_theta_min      6.0540
_cell_measurement_theta_max      81.0410
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.036
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_max          0.212

_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    1.450

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   none
_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     1.54184
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            8064
_reflns_number_total             1847
_diffrn_reflns_av_R_equivalents  0.019
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1847 
# Theoretical number of reflections is about 3735 


_diffrn_reflns_theta_min         6.078
_diffrn_reflns_theta_max         81.287
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        76.446
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -10
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   1.97
_oxford_diffrn_Wilson_scale      0.01

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

_refine_diff_density_min         -0.17
_refine_diff_density_max         0.32


# 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     137
_refine_ls_number_reflns         1814
_refine_ls_R_factor_ref          0.0305
_refine_ls_wR_factor_ref         0.0388
_refine_ls_goodness_of_fit_ref   1.0079
_refine_ls_shift/su_max          0.0004454
_refine_ls_shift/su_mean         0.0000849


# Computed with I/sigma = -10 
_reflns_number_all               1847
_refine_ls_R_factor_all          0.0307
_refine_ls_wR_factor_all         0.0389

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1814
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_gt          0.0388


_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)] 
 302. 356. -21.0 -128. -49.7 
;

# 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 0.03372(9) 0.69976(5) -0.28777(9) 0.0259 1.0000 Uani . . . . . .
C2 C 0.13783(15) 0.62935(8) -0.30885(14) 0.0203 1.0000 Uani . . . . . .
F3 F 0.05434(9) 0.54253(5) -0.31474(9) 0.0279 1.0000 Uani . . . . . .
F4 F 0.12841(10) 0.64318(6) -0.46577(8) 0.0290 1.0000 Uani . . . . . .
C5 C 0.33310(14) 0.63088(7) -0.16290(14) 0.0171 1.0000 Uani . . . . . .
N6 N 0.46060(13) 0.64035(7) -0.21507(12) 0.0191 1.0000 Uani . . . . . .
C7 C 0.63328(15) 0.64365(8) -0.09054(15) 0.0207 1.0000 Uani . . . . . .
F8 F 0.75794(9) 0.65381(6) -0.15147(10) 0.0302 1.0000 Uani . . . . . .
C9 C 0.69083(15) 0.63882(8) 0.08482(15) 0.0222 1.0000 Uani . . . . . .
C10 C 0.55595(15) 0.62671(7) 0.14194(14) 0.0190 1.0000 Uani . . . . . .
C11 C 0.36799(14) 0.62201(7) 0.01403(14) 0.0170 1.0000 Uani . . . . . .
C12 C 0.23060(15) 0.60829(8) 0.07001(15) 0.0216 1.0000 Uani . . . . . .
C13 C 0.27945(17) 0.60037(9) 0.24386(15) 0.0260 1.0000 Uani . . . . . .
C14 C 0.46509(18) 0.60675(9) 0.37098(15) 0.0269 1.0000 Uani . . . . . .
C15 C 0.60021(17) 0.61911(8) 0.32182(15) 0.0248 1.0000 Uani . . . . . .
H91 H 0.8169 0.6417 0.1634 0.0275 1.0000 Uiso R . . . . .
H121 H 0.1043 0.6032 -0.0172 0.0266 1.0000 Uiso R . . . . .
H131 H 0.1898 0.5908 0.2846 0.0318 1.0000 Uiso R . . . . .
H141 H 0.4917 0.6030 0.4912 0.0329 1.0000 Uiso R . . . . .
H151 H 0.7234 0.6221 0.4054 0.0299 1.0000 Uiso R . . . . .
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
F1 0.0195(3) 0.0298(4) 0.0259(4) 0.0011(3) 0.0082(3) 0.0054(3)
C2 0.0212(5) 0.0222(5) 0.0175(5) -0.0002(4) 0.0089(4) -0.0014(4)
F3 0.0229(3) 0.0266(4) 0.0273(4) -0.0017(3) 0.0053(3) -0.0076(3)
F4 0.0282(4) 0.0417(4) 0.0146(3) 0.0006(3) 0.0076(3) -0.0012(3)
C5 0.0187(5) 0.0157(5) 0.0182(5) -0.0012(4) 0.0097(4) -0.0003(4)
N6 0.0223(5) 0.0173(4) 0.0213(4) 0.0001(3) 0.0131(4) 0.0001(3)
C7 0.0186(5) 0.0189(5) 0.0296(6) 0.0020(4) 0.0153(4) 0.0003(4)
F8 0.0226(3) 0.0358(4) 0.0409(4) 0.0057(3) 0.0222(3) 0.0014(3)
C9 0.0162(5) 0.0197(5) 0.0265(6) 0.0012(4) 0.0062(4) -0.0000(4)
C10 0.0209(5) 0.0141(5) 0.0196(5) -0.0006(4) 0.0072(4) 0.0007(4)
C11 0.0188(5) 0.0152(5) 0.0170(5) -0.0015(4) 0.0082(4) 0.0004(4)
C12 0.0229(5) 0.0228(5) 0.0222(5) -0.0001(4) 0.0129(4) 0.0007(4)
C13 0.0361(6) 0.0242(6) 0.0261(6) 0.0013(4) 0.0215(5) 0.0022(5)
C14 0.0425(7) 0.0215(5) 0.0166(5) 0.0012(4) 0.0135(5) 0.0025(5)
C15 0.0291(6) 0.0198(5) 0.0173(5) -0.0000(4) 0.0036(4) 0.0012(4)

_refine_ls_extinction_coef       50(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          7.114(17)
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 . C2 . 1.3437(13) yes
C2 . F3 . 1.3472(13) yes
C2 . F4 . 1.3291(13) yes
C2 . C5 . 1.5157(15) yes
C5 . N6 . 1.3170(13) yes
C5 . C11 . 1.4190(14) yes
N6 . C7 . 1.3279(15) yes
C7 . F8 . 1.3502(12) yes
C7 . C9 . 1.3605(16) yes
C9 . C10 . 1.4080(16) yes
C9 . H91 . 0.941 no
C10 . C11 . 1.4263(15) yes
C10 . C15 . 1.4220(15) yes
C11 . C12 . 1.4231(15) yes
C12 . C13 . 1.3638(16) yes
C12 . H121 . 0.963 no
C13 . C14 . 1.4119(18) yes
C13 . H131 . 0.956 no
C14 . C15 . 1.3627(18) yes
C14 . H141 . 0.955 no
C15 . H151 . 0.935 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
F1 . C2 . F3 . 106.25(9) yes
F1 . C2 . F4 . 106.93(9) yes
F3 . C2 . F4 . 106.92(9) yes
F1 . C2 . C5 . 111.87(9) yes
F3 . C2 . C5 . 111.59(9) yes
F4 . C2 . C5 . 112.88(9) yes
C2 . C5 . N6 . 114.79(9) yes
C2 . C5 . C11 . 120.41(9) yes
N6 . C5 . C11 . 124.80(10) yes
C5 . N6 . C7 . 116.47(9) yes
N6 . C7 . F8 . 113.90(10) yes
N6 . C7 . C9 . 126.46(10) yes
F8 . C7 . C9 . 119.64(10) yes
C7 . C9 . C10 . 117.55(10) yes
C7 . C9 . H91 . 120.3 no
C10 . C9 . H91 . 122.1 no
C9 . C10 . C11 . 118.53(10) yes
C9 . C10 . C15 . 122.49(10) yes
C11 . C10 . C15 . 118.99(10) yes
C10 . C11 . C5 . 116.16(10) yes
C10 . C11 . C12 . 119.05(10) yes
C5 . C11 . C12 . 124.79(10) yes
C11 . C12 . C13 . 119.98(11) yes
C11 . C12 . H121 . 118.6 no
C13 . C12 . H121 . 121.4 no
C12 . C13 . C14 . 121.11(11) yes
C12 . C13 . H131 . 121.5 no
C14 . C13 . H131 . 117.4 no
C13 . C14 . C15 . 120.42(10) yes
C13 . C14 . H141 . 117.8 no
C15 . C14 . H141 . 121.7 no
C10 . C15 . C14 . 120.44(11) yes
C10 . C15 . H151 . 118.9 no
C14 . C15 . H151 . 120.7 no


_iucr_refine_instructions_details 
;
#
# Punched on 27/02/24 at 16:23:36
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
CONT EXTPARAM 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
END                                                                             
#
# Punched on 27/02/24 at 16:23:36
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SINTH/L**2   is  0.100E-02
  Minimum value of RATIO        is   2.00
;

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2336082'
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             
;
2024-02-28 deposited with the CCDC.	2024-06-17 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                   11.6153(7)
_cell_length_b                   5.2160(3)
_cell_length_c                   24.2707(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.344(4)
_cell_angle_gamma                90
_cell_volume                     1470.42(16)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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'
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            4
_chemical_name_systematic        
'(Z)-2,2,2-trifluoro-N-((E)-1-fluoro-2-(phenanthren-9-yl)vinyl)acetimidoyl fluoride'
_chemical_formula_moiety         'C18 H10 F5 N'

# Given Formula = C18 H10 F5 N1 
# Dc =      1.51 Fooo =    680.00 Mu =     11.66 M =    335.27
# Found Formula = C18 H10 F5 N1 
# Dc =      1.51 FOOO =    680.00 Mu =     11.66 M =    335.27

_chemical_formula_sum            'C18 H10 F5 N'
_chemical_compound_source        .
_chemical_formula_weight         335.27


_cell_measurement_reflns_used    6398
_cell_measurement_theta_min      3.6423
_cell_measurement_theta_max      67.5900
_cell_measurement_temperature    180

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.052
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_max          0.410

_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    1.166

# Sheldrick geometric approximatio 0.93 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_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       'Apex3 (Bruker AXS, 2015)'
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_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            20993
_diffrn_reflns_av_unetI/netI     0.183
_reflns_number_total             2706
_diffrn_reflns_av_R_equivalents  0.120
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2706 
# Theoretical number of reflections is about 5480 


_diffrn_reflns_theta_min         3.642
_diffrn_reflns_theta_max         69.096
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        67.023
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   4.03
_oxford_diffrn_Wilson_scale      61.86

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

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.41


# 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     217
_refine_ls_number_reflns         1527
_oxford_refine_ls_R_factor_ref   0.0937
_refine_ls_R_factor_all          0.0937
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_all         0.0808
_refine_ls_goodness_of_fit_ref   0.9374
_refine_ls_shift/su_max          0.0001499
_refine_ls_shift/su_mean         0.0000154


# Computed with I/sigma = -10 
_oxford_reflns_number_all        2706
_oxford_refine_ls_R_factor_all   0.1429
_oxford_refine_ls_wR_factor_all  0.7727

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1527
_refine_ls_R_factor_gt           0.0937
_refine_ls_wR_factor_gt          0.0808


_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)] 
 0.472 0.617 0.439 0.328 
;

# 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 0.6828(4) -0.1697(10) 0.5112(2) 0.0741 1.0000 Uani . . . . . .
C2 C 0.7108(6) -0.0072(14) 0.5524(3) 0.0537 1.0000 Uani . . . . . .
N3 N 0.8187(5) -0.0373(12) 0.5747(2) 0.0522 1.0000 Uani . . . . . .
C4 C 0.8916(8) -0.2069(18) 0.5620(4) 0.0707 1.0000 Uani . . . . . .
F5 F 0.8770(5) -0.3987(11) 0.5266(2) 0.1002 1.0000 Uani . . . . . .
C6 C 1.0088(8) -0.216(2) 0.5877(5) 0.0957 1.0000 Uani . . . . . .
F7 F 1.0858(5) -0.1515(17) 0.5500(3) 0.1333 1.0000 Uani . . . . . .
F8 F 1.0158(6) -0.0647(19) 0.6295(3) 0.1667 1.0000 Uani . . . . . .
F9 F 1.0363(7) -0.4498(17) 0.6035(4) 0.1544 1.0000 Uani . . . . . .
C10 C 0.6351(6) 0.1639(16) 0.5690(3) 0.0551 1.0000 Uani . . . . . .
C11 C 0.6393(6) 0.3577(14) 0.6117(3) 0.0516 1.0000 Uani . . . . . .
C12 C 0.7286(6) 0.3678(14) 0.6490(3) 0.0507 1.0000 Uani . . . . . .
C13 C 0.7354(7) 0.5511(15) 0.6913(3) 0.0551 1.0000 Uani . . . . . .
C14 C 0.6444(7) 0.7347(13) 0.6969(3) 0.0563 1.0000 Uani . . . . . .
C15 C 0.6535(8) 0.9146(16) 0.7402(3) 0.0666 1.0000 Uani . . . . . .
C16 C 0.7447(10) 0.911(2) 0.7755(4) 0.0840 1.0000 Uani . . . . . .
C17 C 0.8328(9) 0.736(2) 0.7700(4) 0.0801 1.0000 Uani . . . . . .
C18 C 0.8275(8) 0.5605(17) 0.7285(4) 0.0707 1.0000 Uani . . . . . .
C19 C 0.5481(6) 0.7237(14) 0.6590(3) 0.0521 1.0000 Uani . . . . . .
C20 C 0.5459(6) 0.5411(15) 0.6167(3) 0.0540 1.0000 Uani . . . . . .
C21 C 0.4510(6) 0.5397(18) 0.5793(4) 0.0679 1.0000 Uani . . . . . .
C22 C 0.3663(7) 0.717(2) 0.5834(4) 0.0799 1.0000 Uani . . . . . .
C23 C 0.3681(7) 0.9018(19) 0.6256(4) 0.0778 1.0000 Uani . . . . . .
C24 C 0.4563(8) 0.9054(16) 0.6626(4) 0.0708 1.0000 Uani . . . . . .
H101 H 0.5649 0.1583 0.5494 0.0705 1.0000 Uiso R . . . . .
H121 H 0.7889 0.2457 0.6459 0.0655 1.0000 Uiso R . . . . .
H151 H 0.5961 1.0380 0.7442 0.0856 1.0000 Uiso R . . . . .
H161 H 0.7480 1.0300 0.8042 0.1022 1.0000 Uiso R . . . . .
H171 H 0.8953 0.7406 0.7944 0.0983 1.0000 Uiso R . . . . .
H181 H 0.8859 0.4401 0.7244 0.0922 1.0000 Uiso R . . . . .
H211 H 0.4470 0.4158 0.5511 0.0834 1.0000 Uiso R . . . . .
H221 H 0.3060 0.7158 0.5577 0.0983 1.0000 Uiso R . . . . .
H231 H 0.3088 1.0203 0.6286 0.0942 1.0000 Uiso R . . . . .
H241 H 0.4578 1.0283 0.6903 0.0872 1.0000 Uiso R . . . . .
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
F1 0.073(3) 0.079(3) 0.071(3) -0.035(3) 0.000(2) 0.002(2)
C2 0.065(5) 0.047(4) 0.049(4) -0.008(3) 0.006(3) -0.008(4)
N3 0.049(3) 0.056(4) 0.052(4) -0.002(3) 0.003(3) 0.008(3)
C4 0.084(6) 0.066(6) 0.062(5) -0.012(4) 0.011(4) 0.014(5)
F5 0.101(4) 0.083(4) 0.116(5) -0.037(4) 0.006(3) 0.028(3)
C6 0.062(6) 0.109(9) 0.116(9) -0.016(7) -0.004(5) 0.053(6)
F7 0.072(4) 0.166(7) 0.162(7) 0.013(6) 0.012(4) 0.021(4)
F8 0.087(4) 0.244(10) 0.169(8) -0.116(8) -0.049(4) 0.067(6)
F9 0.141(6) 0.145(7) 0.176(8) 0.035(6) -0.030(6) 0.063(6)
C10 0.045(4) 0.061(5) 0.059(5) -0.012(4) -0.004(3) 0.004(3)
C11 0.057(4) 0.042(4) 0.056(4) -0.003(3) 0.003(3) 0.002(3)
C12 0.055(4) 0.050(4) 0.047(4) -0.000(3) 0.004(3) 0.009(3)
C13 0.066(4) 0.057(5) 0.042(4) 0.001(4) -0.002(3) -0.016(4)
C14 0.089(5) 0.033(4) 0.047(4) 0.002(3) 0.017(4) -0.005(4)
C15 0.098(6) 0.050(5) 0.052(5) 0.002(4) 0.015(4) -0.005(4)
C16 0.131(9) 0.071(7) 0.050(5) -0.009(5) 0.010(5) -0.021(6)
C17 0.096(7) 0.088(7) 0.057(5) -0.001(5) -0.017(5) -0.031(6)
C18 0.082(6) 0.062(5) 0.068(5) -0.009(5) -0.009(4) 0.003(5)
C19 0.065(4) 0.045(4) 0.046(4) 0.002(3) 0.011(3) 0.006(3)
C20 0.058(4) 0.052(4) 0.053(4) -0.000(4) 0.014(3) 0.006(3)
C21 0.046(4) 0.086(6) 0.071(5) -0.009(5) -0.001(4) 0.016(4)
C22 0.061(5) 0.089(7) 0.090(7) -0.000(6) -0.001(4) 0.012(5)
C23 0.061(5) 0.075(7) 0.098(7) 0.007(5) 0.022(5) 0.026(5)
C24 0.087(6) 0.051(5) 0.075(6) -0.003(4) 0.026(5) 0.008(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1647(6)
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 . C2 . 1.349(8) yes
C2 . N3 . 1.371(9) yes
C2 . C10 . 1.319(10) yes
N3 . C4 . 1.264(10) yes
C4 . F5 . 1.328(10) yes
C4 . C6 . 1.495(13) yes
C6 . F7 . 1.328(13) yes
C6 . F8 . 1.287(13) yes
C6 . F9 . 1.315(13) yes
C10 . C11 . 1.449(10) yes
C10 . H101 . 0.943 no
C11 . C12 . 1.372(9) yes
C11 . C20 . 1.452(10) yes
C12 . C13 . 1.406(10) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.433(11) yes
C13 . C18 . 1.396(10) yes
C14 . C15 . 1.412(11) yes
C14 . C19 . 1.444(11) yes
C15 . C16 . 1.359(12) yes
C15 . H151 . 0.932 no
C16 . C17 . 1.378(14) yes
C16 . H161 . 0.933 no
C17 . C18 . 1.363(12) yes
C17 . H171 . 0.934 no
C18 . H181 . 0.931 no
C19 . C20 . 1.400(10) yes
C19 . C24 . 1.430(11) yes
C20 . C21 . 1.424(10) yes
C21 . C22 . 1.355(12) yes
C21 . H211 . 0.943 no
C22 . C23 . 1.407(13) yes
C22 . H221 . 0.935 no
C23 . C24 . 1.358(12) yes
C23 . H231 . 0.928 no
C24 . H241 . 0.930 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
F1 . C2 . N3 . 115.9(6) yes
F1 . C2 . C10 . 119.6(7) yes
N3 . C2 . C10 . 124.5(7) yes
C2 . N3 . C4 . 126.6(7) yes
N3 . C4 . F5 . 127.0(8) yes
N3 . C4 . C6 . 122.1(9) yes
F5 . C4 . C6 . 110.9(8) yes
C4 . C6 . F7 . 108.5(10) yes
C4 . C6 . F8 . 111.2(7) yes
F7 . C6 . F8 . 110.2(12) yes
C4 . C6 . F9 . 111.9(11) yes
F7 . C6 . F9 . 105.9(8) yes
F8 . C6 . F9 . 109.0(11) yes
C2 . C10 . C11 . 132.2(7) yes
C2 . C10 . H101 . 113.6 no
C11 . C10 . H101 . 114.2 no
C10 . C11 . C12 . 121.4(7) yes
C10 . C11 . C20 . 119.8(7) yes
C12 . C11 . C20 . 118.8(7) yes
C11 . C12 . C13 . 123.1(7) yes
C11 . C12 . H121 . 118.5 no
C13 . C12 . H121 . 118.3 no
C12 . C13 . C14 . 119.0(7) yes
C12 . C13 . C18 . 122.4(8) yes
C14 . C13 . C18 . 118.6(7) yes
C13 . C14 . C15 . 117.5(8) yes
C13 . C14 . C19 . 118.8(6) yes
C15 . C14 . C19 . 123.7(7) yes
C14 . C15 . C16 . 121.0(9) yes
C14 . C15 . H151 . 119.1 no
C16 . C15 . H151 . 119.9 no
C15 . C16 . C17 . 121.6(9) yes
C15 . C16 . H161 . 119.4 no
C17 . C16 . H161 . 119.0 no
C16 . C17 . C18 . 119.1(9) yes
C16 . C17 . H171 . 119.7 no
C18 . C17 . H171 . 121.2 no
C13 . C18 . C17 . 122.2(9) yes
C13 . C18 . H181 . 117.6 no
C17 . C18 . H181 . 120.2 no
C14 . C19 . C20 . 120.3(7) yes
C14 . C19 . C24 . 120.7(7) yes
C20 . C19 . C24 . 119.0(7) yes
C11 . C20 . C19 . 119.9(7) yes
C11 . C20 . C21 . 121.3(7) yes
C19 . C20 . C21 . 118.8(7) yes
C20 . C21 . C22 . 120.7(8) yes
C20 . C21 . H211 . 120.1 no
C22 . C21 . H211 . 119.2 no
C21 . C22 . C23 . 120.9(9) yes
C21 . C22 . H221 . 119.3 no
C23 . C22 . H221 . 119.9 no
C22 . C23 . C24 . 119.9(8) yes
C22 . C23 . H231 . 120.4 no
C24 . C23 . H231 . 119.7 no
C19 . C24 . C23 . 120.7(8) yes
C19 . C24 . H241 . 119.3 no
C23 . C24 . H241 . 120.0 no
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
C12 . H121 . N3 . 127 0.95 2.30 2.972(12) yes


_iucr_refine_instructions_details 
;
#
# Punched on 20/12/23 at 20:37:41
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
END                                                                             
#
# Punched on 20/12/23 at 20:37:41
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2336081'
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             
;
2024-02-28 deposited with the CCDC.	2024-06-17 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. 
;


#--------------------------------------------------------------- 
# _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                   13.5573(4)
_cell_length_b                   16.3320(5)
_cell_length_c                   8.8755(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.9980(14)
_cell_angle_gamma                90
_cell_volume                     1935.35(11)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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            8
_chemical_name_systematic        
3-Fluoro-7-nitro-1-(trifluoromethyl)isoquinoline
_chemical_formula_moiety         'C10 H4 F4 N2 O2'

# Given Formula = C10 H4 F4 N2 O2 
# Dc =      1.79 Fooo =   1040.00 Mu =     15.90 M =    260.15
# Found Formula = C10 H4 F4 N2 O2 
# Dc =      1.79 FOOO =   1040.00 Mu =     15.90 M =    260.15

_chemical_formula_sum            'C10 H4 F4 N2 O2'
_chemical_compound_source        .
_chemical_formula_weight         260.15


_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      4.2771
_cell_measurement_theta_max      68.2900
_cell_measurement_temperature    180

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.070
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_max          0.336

_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    1.590

# Sheldrick geometric approximatio 0.87 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_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       'Apex3 (Bruker AXS, 2015)'
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_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            38767
_reflns_number_total             3554
_diffrn_reflns_av_R_equivalents  0.042
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3554 
# Theoretical number of reflections is about 7117 


_diffrn_reflns_theta_min         3.310
_diffrn_reflns_theta_max         68.434
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        68.434
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   2.70
_oxford_diffrn_Wilson_scale      263.94

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

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.22


# 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     326
_refine_ls_number_reflns         2993
_refine_ls_R_factor_ref          0.0326
_refine_ls_wR_factor_ref         0.0437
_refine_ls_goodness_of_fit_ref   1.0272
_refine_ls_shift/su_max          0.0004430
_refine_ls_shift/su_mean         0.0000533


# Computed with I/sigma = -10 
_reflns_number_all               3554
_refine_ls_R_factor_all          0.0412
_refine_ls_wR_factor_all         0.0631

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2993
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_gt          0.0437


_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)] 
 0.619E-01 0.755E-01 0.146E-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 0.73756(8) 0.69804(6) 0.08577(12) 0.0380 1.0000 Uani . . . . . .
C2 C 0.69199(13) 0.75067(11) -0.0197(2) 0.0300 1.0000 Uani . . . . . .
F3 F 0.67291(8) 0.70889(6) -0.15188(12) 0.0366 1.0000 Uani . . . . . .
F4 F 0.60493(8) 0.77097(7) 0.01733(13) 0.0409 1.0000 Uani . . . . . .
C5 C 0.75749(12) 0.82455(10) -0.03474(19) 0.0278 1.0000 Uani . . . . . .
N6 N 0.72034(11) 0.89505(9) 0.00083(17) 0.0319 1.0000 Uani . . . . . .
C7 C 0.77321(14) 0.96167(11) -0.0197(2) 0.0340 1.0000 Uani . . . . . .
F8 F 0.73204(9) 1.03219(6) 0.02026(14) 0.0446 1.0000 Uani . . . . . .
C9 C 0.85909(14) 0.96465(11) -0.0785(2) 0.0335 1.0000 Uani . . . . . .
C10 C 0.89938(13) 0.88951(11) -0.1170(2) 0.0302 1.0000 Uani . . . . . .
C11 C 0.84908(12) 0.81576(10) -0.08990(18) 0.0272 1.0000 Uani . . . . . .
C12 C 0.88904(12) 0.73980(10) -0.12688(19) 0.0289 1.0000 Uani . . . . . .
C13 C 0.97324(13) 0.74007(11) -0.1919(2) 0.0307 1.0000 Uani . . . . . .
N14 N 1.01172(12) 0.66082(10) -0.23506(19) 0.0371 1.0000 Uani . . . . . .
O15 O 0.96760(13) 0.59862(9) -0.2110(2) 0.0647 1.0000 Uani . . . . . .
O16 O 1.08543(11) 0.66119(9) -0.29634(19) 0.0524 1.0000 Uani . . . . . .
C17 C 1.02321(13) 0.81225(12) -0.2233(2) 0.0348 1.0000 Uani . . . . . .
C18 C 0.98699(13) 0.88542(12) -0.1849(2) 0.0354 1.0000 Uani . . . . . .
F19 F 0.76734(9) 0.30078(7) 0.48477(15) 0.0482 1.0000 Uani . . . . . .
C20 C 0.72949(14) 0.22950(11) 0.5254(2) 0.0352 1.0000 Uani . . . . . .
N21 N 0.76999(11) 0.16369(9) 0.47126(18) 0.0339 1.0000 Uani . . . . . .
C22 C 0.73622(13) 0.09206(11) 0.5068(2) 0.0303 1.0000 Uani . . . . . .
C23 C 0.66073(13) 0.08121(10) 0.59791(19) 0.0289 1.0000 Uani . . . . . .
C24 C 0.62253(12) 0.00413(11) 0.63375(19) 0.0292 1.0000 Uani . . . . . .
C25 C 0.54946(12) 0.00259(11) 0.7223(2) 0.0301 1.0000 Uani . . . . . .
N26 N 0.50792(11) -0.07758(10) 0.75400(18) 0.0352 1.0000 Uani . . . . . .
O27 O 0.53512(12) -0.13827(8) 0.69235(18) 0.0479 1.0000 Uani . . . . . .
O28 O 0.44726(12) -0.07940(9) 0.8413(2) 0.0552 1.0000 Uani . . . . . .
C29 C 0.51056(13) 0.07337(12) 0.7815(2) 0.0345 1.0000 Uani . . . . . .
C30 C 0.54650(13) 0.14726(11) 0.7477(2) 0.0340 1.0000 Uani . . . . . .
C31 C 0.62143(13) 0.15385(11) 0.6546(2) 0.0305 1.0000 Uani . . . . . .
C32 C 0.65774(14) 0.23028(11) 0.6143(2) 0.0354 1.0000 Uani . . . . . .
C33 C 0.78544(14) 0.01930(11) 0.4447(2) 0.0360 1.0000 Uani . . . . . .
F34 F 0.71844(10) -0.02893(7) 0.35783(14) 0.0503 1.0000 Uani . . . . . .
F35 F 0.85133(11) 0.04141(7) 0.35946(18) 0.0635 1.0000 Uani . . . . . .
F36 F 0.83182(9) -0.02838(7) 0.55698(14) 0.0498 1.0000 Uani . . . . . .
H91 H 0.8897 1.0150 -0.0932 0.0405 1.0000 Uiso R . . . . .
H121 H 0.8593 0.6905 -0.1075 0.0342 1.0000 Uiso R . . . . .
H171 H 1.0797 0.8111 -0.2732 0.0403 1.0000 Uiso R . . . . .
H181 H 1.0200 0.9344 -0.2017 0.0413 1.0000 Uiso R . . . . .
H291 H 0.4610 0.0678 0.8446 0.0413 1.0000 Uiso R . . . . .
H301 H 0.5226 0.1941 0.7857 0.0409 1.0000 Uiso R . . . . .
H321 H 0.6341 0.2802 0.6492 0.0424 1.0000 Uiso R . . . . .
H241 H 0.6472 -0.0452 0.5989 0.0366 1.0000 Uiso R . . . . .
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
F1 0.0417(6) 0.0342(6) 0.0387(6) 0.0098(4) 0.0084(5) -0.0032(5)
C2 0.0301(9) 0.0301(9) 0.0313(9) 0.0001(7) 0.0099(7) -0.0013(7)
F3 0.0366(5) 0.0372(6) 0.0369(6) -0.0051(4) 0.0090(4) -0.0108(4)
F4 0.0338(6) 0.0416(6) 0.0526(7) 0.0028(5) 0.0225(5) -0.0016(5)
C5 0.0286(8) 0.0294(9) 0.0260(8) 0.0007(6) 0.0067(6) -0.0021(7)
N6 0.0342(8) 0.0291(8) 0.0335(8) -0.0003(6) 0.0089(6) -0.0002(6)
C7 0.0399(10) 0.0268(9) 0.0359(10) -0.0023(7) 0.0080(8) 0.0005(7)
F8 0.0518(7) 0.0263(5) 0.0598(7) -0.0047(5) 0.0210(6) 0.0060(5)
C9 0.0395(10) 0.0258(9) 0.0351(9) 0.0009(7) 0.0065(8) -0.0068(7)
C10 0.0317(9) 0.0300(9) 0.0294(9) 0.0015(7) 0.0064(7) -0.0062(7)
C11 0.0292(8) 0.0276(8) 0.0247(8) 0.0014(6) 0.0043(6) -0.0031(7)
C12 0.0278(8) 0.0296(9) 0.0300(9) 0.0027(7) 0.0067(7) -0.0038(7)
C13 0.0311(9) 0.0312(9) 0.0302(9) 0.0003(7) 0.0062(7) 0.0008(7)
N14 0.0345(8) 0.0363(9) 0.0427(9) -0.0018(7) 0.0129(7) 0.0018(7)
O15 0.0703(11) 0.0311(8) 0.1057(15) -0.0013(8) 0.0518(10) -0.0015(7)
O16 0.0467(8) 0.0497(9) 0.0687(10) -0.0057(7) 0.0321(8) 0.0029(7)
C17 0.0290(9) 0.0410(10) 0.0367(10) 0.0002(8) 0.0119(7) -0.0051(8)
C18 0.0341(9) 0.0344(10) 0.0397(10) 0.0011(8) 0.0119(8) -0.0100(8)
F19 0.0533(7) 0.0275(6) 0.0673(8) 0.0050(5) 0.0205(6) -0.0051(5)
C20 0.0365(9) 0.0266(9) 0.0421(10) 0.0027(8) 0.0057(8) -0.0012(7)
N21 0.0340(8) 0.0312(8) 0.0378(8) 0.0027(6) 0.0095(6) -0.0001(6)
C22 0.0302(9) 0.0299(9) 0.0315(9) 0.0007(7) 0.0075(7) 0.0014(7)
C23 0.0273(8) 0.0300(9) 0.0294(9) 0.0006(7) 0.0053(7) 0.0040(7)
C24 0.0289(8) 0.0293(9) 0.0304(9) 0.0001(7) 0.0080(7) 0.0045(7)
C25 0.0272(9) 0.0324(9) 0.0311(9) 0.0025(7) 0.0064(7) 0.0018(7)
N26 0.0324(8) 0.0367(9) 0.0382(8) 0.0052(7) 0.0110(7) 0.0002(6)
O27 0.0614(9) 0.0327(7) 0.0562(9) -0.0043(6) 0.0282(7) -0.0036(7)
O28 0.0529(9) 0.0476(9) 0.0761(11) 0.0077(8) 0.0423(8) -0.0010(7)
C29 0.0268(9) 0.0422(11) 0.0360(10) -0.0020(8) 0.0098(7) 0.0046(7)
C30 0.0300(9) 0.0346(10) 0.0381(10) -0.0065(8) 0.0079(7) 0.0068(7)
C31 0.0275(8) 0.0316(9) 0.0316(9) -0.0009(7) 0.0033(7) 0.0045(7)
C32 0.0348(9) 0.0272(9) 0.0436(10) -0.0031(8) 0.0052(8) 0.0053(7)
C33 0.0394(10) 0.0317(9) 0.0417(10) 0.0032(8) 0.0206(8) -0.0001(8)
F34 0.0608(8) 0.0418(7) 0.0511(7) -0.0149(5) 0.0170(6) -0.0018(6)
F35 0.0768(9) 0.0389(7) 0.0929(11) 0.0015(7) 0.0655(8) 0.0015(6)
F36 0.0523(7) 0.0442(7) 0.0547(7) 0.0058(5) 0.0137(6) 0.0202(6)

_refine_ls_extinction_coef       5.0(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.06490(11)
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 . C2 . 1.340(2) yes
C2 . F3 . 1.343(2) yes
C2 . F4 . 1.321(2) yes
C2 . C5 . 1.518(2) yes
C5 . N6 . 1.317(2) yes
C5 . C11 . 1.419(2) yes
N6 . C7 . 1.333(2) yes
C7 . F8 . 1.354(2) yes
C7 . C9 . 1.357(3) yes
C9 . C10 . 1.409(3) yes
C9 . H91 . 0.941 no
C10 . C11 . 1.425(2) yes
C10 . C18 . 1.423(2) yes
C11 . C12 . 1.415(2) yes
C12 . C13 . 1.365(2) yes
C12 . H121 . 0.929 no
C13 . N14 . 1.471(2) yes
C13 . C17 . 1.411(2) yes
N14 . O15 . 1.217(2) yes
N14 . O16 . 1.218(2) yes
C17 . C18 . 1.358(3) yes
C17 . H171 . 0.949 no
C18 . H181 . 0.941 no
F19 . C20 . 1.347(2) yes
C20 . N21 . 1.334(2) yes
C20 . C32 . 1.355(3) yes
N21 . C22 . 1.315(2) yes
C22 . C23 . 1.421(2) yes
C22 . C33 . 1.513(2) yes
C23 . C24 . 1.418(2) yes
C23 . C31 . 1.427(2) yes
C24 . C25 . 1.367(2) yes
C24 . H241 . 0.945 no
C25 . N26 . 1.472(2) yes
C25 . C29 . 1.410(2) yes
N26 . O27 . 1.220(2) yes
N26 . O28 . 1.225(2) yes
C29 . C30 . 1.354(3) yes
C29 . H291 . 0.951 no
C30 . C31 . 1.421(2) yes
C30 . H301 . 0.918 no
C31 . C32 . 1.410(3) yes
C32 . H321 . 0.947 no
C33 . F34 . 1.341(2) yes
C33 . F35 . 1.317(2) yes
C33 . F36 . 1.333(2) yes
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
F1 . C2 . F3 . 106.25(13) yes
F1 . C2 . F4 . 108.11(14) yes
F3 . C2 . F4 . 107.45(14) yes
F1 . C2 . C5 . 111.44(14) yes
F3 . C2 . C5 . 110.72(13) yes
F4 . C2 . C5 . 112.59(14) yes
C2 . C5 . N6 . 114.83(14) yes
C2 . C5 . C11 . 120.70(15) yes
N6 . C5 . C11 . 124.41(15) yes
C5 . N6 . C7 . 116.36(15) yes
N6 . C7 . F8 . 113.76(16) yes
N6 . C7 . C9 . 126.83(17) yes
F8 . C7 . C9 . 119.38(16) yes
C7 . C9 . C10 . 117.19(16) yes
C7 . C9 . H91 . 120.9 no
C10 . C9 . H91 . 121.9 no
C9 . C10 . C11 . 118.55(16) yes
C9 . C10 . C18 . 122.05(16) yes
C11 . C10 . C18 . 119.39(16) yes
C10 . C11 . C5 . 116.48(15) yes
C10 . C11 . C12 . 119.22(15) yes
C5 . C11 . C12 . 124.19(15) yes
C11 . C12 . C13 . 118.48(16) yes
C11 . C12 . H121 . 121.4 no
C13 . C12 . H121 . 120.1 no
C12 . C13 . N14 . 117.87(16) yes
C12 . C13 . C17 . 123.47(16) yes
N14 . C13 . C17 . 118.63(15) yes
C13 . N14 . O15 . 118.78(15) yes
C13 . N14 . O16 . 117.88(15) yes
O15 . N14 . O16 . 123.32(17) yes
C13 . C17 . C18 . 118.58(16) yes
C13 . C17 . H171 . 121.9 no
C18 . C17 . H171 . 119.4 no
C10 . C18 . C17 . 120.82(16) yes
C10 . C18 . H181 . 118.8 no
C17 . C18 . H181 . 120.4 no
F19 . C20 . N21 . 113.58(16) yes
F19 . C20 . C32 . 119.58(17) yes
N21 . C20 . C32 . 126.84(17) yes
C20 . N21 . C22 . 116.62(16) yes
N21 . C22 . C23 . 124.25(16) yes
N21 . C22 . C33 . 114.68(15) yes
C23 . C22 . C33 . 121.07(15) yes
C22 . C23 . C24 . 124.43(16) yes
C22 . C23 . C31 . 116.53(16) yes
C24 . C23 . C31 . 119.04(15) yes
C23 . C24 . C25 . 118.32(16) yes
C23 . C24 . H241 . 121.3 no
C25 . C24 . H241 . 120.4 no
C24 . C25 . N26 . 117.77(16) yes
C24 . C25 . C29 . 123.69(17) yes
N26 . C25 . C29 . 118.53(15) yes
C25 . N26 . O27 . 118.79(15) yes
C25 . N26 . O28 . 117.66(15) yes
O27 . N26 . O28 . 123.56(16) yes
C25 . C29 . C30 . 118.40(17) yes
C25 . C29 . H291 . 119.4 no
C30 . C29 . H291 . 122.2 no
C29 . C30 . C31 . 121.17(16) yes
C29 . C30 . H301 . 119.9 no
C31 . C30 . H301 . 118.9 no
C23 . C31 . C30 . 119.37(16) yes
C23 . C31 . C32 . 118.57(16) yes
C30 . C31 . C32 . 122.06(16) yes
C31 . C32 . C20 . 117.18(16) yes
C31 . C32 . H321 . 121.7 no
C20 . C32 . H321 . 121.1 no
C22 . C33 . F34 . 111.93(15) yes
C22 . C33 . F35 . 112.32(15) yes
F34 . C33 . F35 . 106.86(16) yes
C22 . C33 . F36 . 111.54(15) yes
F34 . C33 . F36 . 105.74(15) yes
F35 . C33 . F36 . 108.09(16) 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
C32 . H321 . O28 3_656 163 0.95 2.55 3.469(3) yes


_iucr_refine_instructions_details 
;
#
# Punched on 27/02/24 at 14:56:25
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
CONT EXTPARAM 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
END                                                                             
#
# Punched on 27/02/24 at 14:56:25
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SINTH/L**2   is  0.100E-02
  Minimum value of RATIO        is   2.00
;

