# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 2251498'
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             
;
2023-03-24 deposited with the CCDC.	2023-05-22 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                   9.2049(3)
_cell_length_b                   11.1696(4)
_cell_length_c                   11.5661(4)
_cell_angle_alpha                100.8672(13)
_cell_angle_beta                 106.0273(12)
_cell_angle_gamma                94.3334(12)
_cell_volume                     1112.14(7)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .
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        
(E)-N-(1-(bis(4-methylbenzyl)amino)-2-phenylethylidene)-2,2,2-trifluoroacetamide
_chemical_formula_moiety         'C26 H25 F3 N2 O'

# Given Formula = C26 H26 F3 N2 O1 
# Dc =      1.31 Fooo =    460.00 Mu =      8.09 M =    439.50
# Found Formula = C26 H25 F3 N2 O1 
# Dc =      1.31 FOOO =    460.00 Mu =      8.09 M =    438.49

_chemical_formula_sum            'C26 H25 F3 N2 O'
_chemical_compound_source        ?
_chemical_formula_weight         438.49


_cell_measurement_reflns_used    9706
_cell_measurement_theta_min      4.0675
_cell_measurement_theta_max      68.2917
_cell_measurement_temperature    180

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.136
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_max          0.552

_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.809

# Sheldrick geometric approximatio 0.74 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_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       '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            41508
_reflns_number_total             4048
_diffrn_reflns_av_R_equivalents  0.035
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4048 
# Theoretical number of reflections is about 8154 


_diffrn_reflns_theta_min         4.067
_diffrn_reflns_theta_max         68.285
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        68.285
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -11
_reflns_limit_h_max              10
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.77
_oxford_diffrn_Wilson_scale      12.86

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

_refine_diff_density_min         -0.63
_refine_diff_density_max         0.83


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_number_parameters     290
_oxford_refine_ls_R_factor_ref   0.0598
_refine_ls_wR_factor_ref         0.0637
_refine_ls_goodness_of_fit_ref   1.1073
_refine_ls_shift/su_max          0.0001943
_refine_ls_shift/su_mean         0.0000217


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4048
_refine_ls_R_factor_all          0.0621
_refine_ls_wR_factor_all         0.0679

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3872
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_gt          0.0637


_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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.262 0.187 0.716E-01 0.133E-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 -0.35728(15) 0.33227(13) 0.4045(2) 0.0764 1.0000 Uani . . . . . .
C2 C -0.2158(2) 0.34273(17) 0.40114(19) 0.0346 1.0000 Uani . . . . . .
F3 F -0.14905(18) 0.44046(13) 0.48921(19) 0.0781 1.0000 Uani . . . . . .
F4 F -0.2087(3) 0.3714(2) 0.29966(18) 0.1119 1.0000 Uani . . . . . .
C5 C -0.1410(2) 0.22689(16) 0.42199(17) 0.0299 1.0000 Uani . . . . . .
O6 O -0.22400(16) 0.13196(12) 0.41000(16) 0.0455 1.0000 Uani . . . . . .
N7 N 0.00919(17) 0.24732(14) 0.44100(15) 0.0307 1.0000 Uani . . . . . .
C8 C 0.11153(19) 0.19036(15) 0.50669(16) 0.0260 1.0000 Uani . . . . . .
N9 N 0.24329(16) 0.18354(13) 0.48107(14) 0.0271 1.0000 Uani . . . . . .
C10 C 0.37822(19) 0.14388(16) 0.55794(17) 0.0287 1.0000 Uani . . . . . .
C11 C 0.5040(2) 0.24968(16) 0.62710(16) 0.0272 1.0000 Uani . . . . . .
C12 C 0.6504(2) 0.22348(17) 0.67743(18) 0.0331 1.0000 Uani . . . . . .
C13 C 0.7685(2) 0.31681(18) 0.74203(19) 0.0362 1.0000 Uani . . . . . .
C14 C 0.7452(2) 0.43970(18) 0.75738(17) 0.0328 1.0000 Uani . . . . . .
C15 C 0.5989(2) 0.46557(17) 0.70705(18) 0.0329 1.0000 Uani . . . . . .
C16 C 0.4798(2) 0.37229(17) 0.64321(17) 0.0313 1.0000 Uani . . . . . .
C17 C 0.8751(2) 0.5416(2) 0.8242(2) 0.0437 1.0000 Uani . . . . . .
C18 C 0.2659(2) 0.22219(17) 0.37133(17) 0.0307 1.0000 Uani . . . . . .
C19 C 0.2514(2) 0.11287(17) 0.26732(17) 0.0302 1.0000 Uani . . . . . .
C20 C 0.3762(2) 0.08659(19) 0.22636(19) 0.0385 1.0000 Uani . . . . . .
C21 C 0.3615(3) -0.0123(2) 0.1291(2) 0.0444 1.0000 Uani . . . . . .
C22 C 0.2243(3) -0.0877(2) 0.07119(19) 0.0423 1.0000 Uani . . . . . .
C23 C 0.1007(2) -0.0622(2) 0.11383(19) 0.0421 1.0000 Uani . . . . . .
C24 C 0.1136(2) 0.03645(19) 0.20993(18) 0.0371 1.0000 Uani . . . . . .
C25 C 0.2101(3) -0.1962(3) -0.0330(3) 0.0655 1.0000 Uani . . . . . .
C26 C 0.0877(2) 0.14234(16) 0.61527(17) 0.0280 1.0000 Uani . . . . . .
C27 C 0.1801(2) 0.22169(16) 0.73923(17) 0.0290 1.0000 Uani . . . . . .
C28 C 0.2623(2) 0.1683(2) 0.83082(19) 0.0396 1.0000 Uani . . . . . .
C29 C 0.3461(3) 0.2407(2) 0.9447(2) 0.0506 1.0000 Uani . . . . . .
C30 C 0.3486(3) 0.3668(2) 0.9675(2) 0.0498 1.0000 Uani . . . . . .
C31 C 0.2662(3) 0.4208(2) 0.8772(2) 0.0456 1.0000 Uani . . . . . .
C32 C 0.1819(2) 0.34862(18) 0.76357(19) 0.0357 1.0000 Uani . . . . . .
H101 H 0.3488 0.1014 0.6157 0.0353 1.0000 Uiso R . . . . .
H102 H 0.4152 0.0851 0.5023 0.0352 1.0000 Uiso R . . . . .
H121 H 0.6709 0.1406 0.6656 0.0394 1.0000 Uiso R . . . . .
H131 H 0.8661 0.2962 0.7757 0.0436 1.0000 Uiso R . . . . .
H151 H 0.5810 0.5487 0.7154 0.0397 1.0000 Uiso R . . . . .
H161 H 0.3787 0.3929 0.6120 0.0376 1.0000 Uiso R . . . . .
H171 H 0.8382 0.6178 0.8517 0.0661 1.0000 Uiso R . . . . .
H173 H 0.9451 0.5201 0.8926 0.0666 1.0000 Uiso R . . . . .
H172 H 0.9316 0.5581 0.7667 0.0653 1.0000 Uiso R . . . . .
H181 H 0.3687 0.2680 0.3954 0.0361 1.0000 Uiso R . . . . .
H182 H 0.1903 0.2775 0.3449 0.0374 1.0000 Uiso R . . . . .
H201 H 0.4717 0.1364 0.2651 0.0457 1.0000 Uiso R . . . . .
H211 H 0.4473 -0.0286 0.1016 0.0539 1.0000 Uiso R . . . . .
H231 H 0.0052 -0.1126 0.0747 0.0507 1.0000 Uiso R . . . . .
H241 H 0.0264 0.0530 0.2370 0.0454 1.0000 Uiso R . . . . .
H251 H 0.1074 -0.2225 -0.0839 0.0994 1.0000 Uiso R . . . . .
H253 H 0.2519 -0.2641 -0.0009 0.0990 1.0000 Uiso R . . . . .
H252 H 0.2701 -0.1752 -0.0831 0.0997 1.0000 Uiso R . . . . .
H261 H -0.0188 0.1400 0.6095 0.0342 1.0000 Uiso R . . . . .
H262 H 0.1139 0.0596 0.6086 0.0337 1.0000 Uiso R . . . . .
H281 H 0.2630 0.0813 0.8148 0.0482 1.0000 Uiso R . . . . .
H291 H 0.4022 0.2012 1.0068 0.0608 1.0000 Uiso R . . . . .
H301 H 0.4068 0.4161 1.0434 0.0599 1.0000 Uiso R . . . . .
H311 H 0.2682 0.5088 0.8924 0.0550 1.0000 Uiso R . . . . .
H321 H 0.1259 0.3868 0.7024 0.0430 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       52(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.3022(7)
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 . 1.310(2) yes
C2 . F3 . 1.319(2) yes
C2 . F4 . 1.290(3) yes
C2 . C5 . 1.539(3) yes
C5 . O6 . 1.221(2) yes
C5 . N7 . 1.333(2) yes
N7 . C8 . 1.322(2) yes
C8 . N9 . 1.330(2) yes
C8 . C26 . 1.517(2) yes
N9 . C10 . 1.467(2) yes
N9 . C18 . 1.476(2) yes
C10 . C11 . 1.517(2) yes
C10 . H101 . 0.972 no
C10 . H102 . 0.978 no
C11 . C12 . 1.390(3) yes
C11 . C16 . 1.390(3) yes
C12 . C13 . 1.383(3) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.391(3) yes
C13 . H131 . 0.941 no
C14 . C15 . 1.387(3) yes
C14 . C17 . 1.508(3) yes
C15 . C16 . 1.387(3) yes
C15 . H151 . 0.947 no
C16 . H161 . 0.963 no
C17 . H171 . 0.970 no
C17 . H173 . 0.956 no
C17 . H172 . 0.985 no
C18 . C19 . 1.513(3) yes
C18 . H181 . 0.981 no
C18 . H182 . 0.989 no
C19 . C20 . 1.389(3) yes
C19 . C24 . 1.391(3) yes
C20 . C21 . 1.389(3) yes
C20 . H201 . 0.948 no
C21 . C22 . 1.383(3) yes
C21 . H211 . 0.946 no
C22 . C23 . 1.387(3) yes
C22 . C25 . 1.508(3) yes
C23 . C24 . 1.382(3) yes
C23 . H231 . 0.951 no
C24 . H241 . 0.957 no
C25 . H251 . 0.955 no
C25 . H253 . 0.965 no
C25 . H252 . 0.951 no
C26 . C27 . 1.516(2) yes
C26 . H261 . 0.962 no
C26 . H262 . 0.967 no
C27 . C28 . 1.383(3) yes
C27 . C32 . 1.390(3) yes
C28 . C29 . 1.388(3) yes
C28 . H281 . 0.955 no
C29 . C30 . 1.381(4) yes
C29 . H291 . 0.963 no
C30 . C31 . 1.377(4) yes
C30 . H301 . 0.935 no
C31 . C32 . 1.386(3) yes
C31 . H311 . 0.963 no
C32 . H321 . 0.945 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 . 103.43(18) yes
F1 . C2 . F4 . 110.3(2) yes
F3 . C2 . F4 . 105.9(2) yes
F1 . C2 . C5 . 112.24(16) yes
F3 . C2 . C5 . 112.46(16) yes
F4 . C2 . C5 . 112.01(17) yes
C2 . C5 . O6 . 118.09(16) yes
C2 . C5 . N7 . 111.23(15) yes
O6 . C5 . N7 . 130.42(17) yes
C5 . N7 . C8 . 125.40(16) yes
N7 . C8 . N9 . 118.09(16) yes
N7 . C8 . C26 . 122.02(16) yes
N9 . C8 . C26 . 119.72(15) yes
C8 . N9 . C10 . 124.91(15) yes
C8 . N9 . C18 . 120.78(14) yes
C10 . N9 . C18 . 114.26(14) yes
N9 . C10 . C11 . 112.83(14) yes
N9 . C10 . H101 . 109.5 no
C11 . C10 . H101 . 110.0 no
N9 . C10 . H102 . 106.5 no
C11 . C10 . H102 . 109.6 no
H101 . C10 . H102 . 108.2 no
C10 . C11 . C12 . 118.80(15) yes
C10 . C11 . C16 . 123.09(16) yes
C12 . C11 . C16 . 118.11(17) yes
C11 . C12 . C13 . 120.87(17) yes
C11 . C12 . H121 . 119.9 no
C13 . C12 . H121 . 119.2 no
C12 . C13 . C14 . 121.24(17) yes
C12 . C13 . H131 . 118.9 no
C14 . C13 . H131 . 119.8 no
C13 . C14 . C15 . 117.76(17) yes
C13 . C14 . C17 . 121.18(17) yes
C15 . C14 . C17 . 121.05(18) yes
C14 . C15 . C16 . 121.27(17) yes
C14 . C15 . H151 . 119.1 no
C16 . C15 . H151 . 119.6 no
C11 . C16 . C15 . 120.74(17) yes
C11 . C16 . H161 . 119.8 no
C15 . C16 . H161 . 119.4 no
C14 . C17 . H171 . 111.5 no
C14 . C17 . H173 . 112.1 no
H171 . C17 . H173 . 109.7 no
C14 . C17 . H172 . 108.9 no
H171 . C17 . H172 . 106.6 no
H173 . C17 . H172 . 107.8 no
N9 . C18 . C19 . 111.64(14) yes
N9 . C18 . H181 . 107.7 no
C19 . C18 . H181 . 109.2 no
N9 . C18 . H182 . 108.8 no
C19 . C18 . H182 . 110.5 no
H181 . C18 . H182 . 108.9 no
C18 . C19 . C20 . 120.50(17) yes
C18 . C19 . C24 . 121.26(17) yes
C20 . C19 . C24 . 118.24(18) yes
C19 . C20 . C21 . 120.31(19) yes
C19 . C20 . H201 . 119.7 no
C21 . C20 . H201 . 120.0 no
C20 . C21 . C22 . 121.5(2) yes
C20 . C21 . H211 . 119.4 no
C22 . C21 . H211 . 119.1 no
C21 . C22 . C23 . 117.88(19) yes
C21 . C22 . C25 . 121.1(2) yes
C23 . C22 . C25 . 121.0(2) yes
C22 . C23 . C24 . 121.12(19) yes
C22 . C23 . H231 . 119.1 no
C24 . C23 . H231 . 119.8 no
C19 . C24 . C23 . 120.91(19) yes
C19 . C24 . H241 . 119.4 no
C23 . C24 . H241 . 119.6 no
C22 . C25 . H251 . 113.0 no
C22 . C25 . H253 . 110.2 no
H251 . C25 . H253 . 109.6 no
C22 . C25 . H252 . 109.6 no
H251 . C25 . H252 . 108.4 no
H253 . C25 . H252 . 105.8 no
C8 . C26 . C27 . 113.44(14) yes
C8 . C26 . H261 . 107.6 no
C27 . C26 . H261 . 108.5 no
C8 . C26 . H262 . 108.4 no
C27 . C26 . H262 . 109.8 no
H261 . C26 . H262 . 109.1 no
C26 . C27 . C28 . 120.29(17) yes
C26 . C27 . C32 . 120.80(17) yes
C28 . C27 . C32 . 118.91(18) yes
C27 . C28 . C29 . 120.4(2) yes
C27 . C28 . H281 . 119.7 no
C29 . C28 . H281 . 119.9 no
C28 . C29 . C30 . 120.3(2) yes
C28 . C29 . H291 . 118.7 no
C30 . C29 . H291 . 121.1 no
C29 . C30 . C31 . 119.8(2) yes
C29 . C30 . H301 . 120.5 no
C31 . C30 . H301 . 119.7 no
C30 . C31 . C32 . 120.1(2) yes
C30 . C31 . H311 . 120.1 no
C32 . C31 . H311 . 119.8 no
C27 . C32 . C31 . 120.6(2) yes
C27 . C32 . H321 . 120.2 no
C31 . C32 . H321 . 119.2 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
C26 . H261 . O6 . 123.02(5) 0.962 2.528 3.157(3) yes
C26 . H262 . O6 2_556 169.62(5) 0.967 2.434 3.390(3) yes



####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2251499'
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             
;
2023-03-24 deposited with the CCDC.	2023-05-22 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                   11.4557(5)
_cell_length_b                   5.2006(2)
_cell_length_c                   13.2348(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.7150(18)
_cell_angle_gamma                90
_cell_volume                     742.26(5)
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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        
N-(perfluoroethyl)-2-(phenanthren-9-yl)ethen-1-imine
_chemical_formula_moiety         'C18 H10 F5 N'

# Given Formula = C17 H9 F5 N1 O1 
# Dc =      1.51 Fooo =    340.00 Mu =     12.13 M =    338.25
# Found Formula = C18 H10 F5 N1 
# Dc =      1.50 FOOO =    340.00 Mu =     11.55 M =    335.27

_chemical_formula_sum            'C18 H10 F5 N'
_chemical_compound_source        ?
_chemical_formula_weight         335.27


_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      3.5475
_cell_measurement_theta_max      68.4192
_cell_measurement_temperature    180

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.047
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_max          0.956

_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    1.155

# Sheldrick geometric approximatio 0.94 0.95 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.95
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_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       '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            16615
_reflns_number_total             2691
_diffrn_reflns_av_R_equivalents  0.029
# Number of reflections without Friedels Law is 2691 
# Number of reflections with Friedels Law is 1530 
# Theoretical number of reflections is about 1364 


_diffrn_reflns_theta_min         3.547
_diffrn_reflns_theta_max         68.414
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        68.414
_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       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              -6
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   3.52
_oxford_diffrn_Wilson_scale      10.90

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

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.88


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     1
_refine_ls_number_parameters     218
_oxford_refine_ls_R_factor_ref   0.0618
_refine_ls_wR_factor_ref         0.0689
_refine_ls_goodness_of_fit_ref   1.0691
_refine_ls_shift/su_max          0.0001481
_refine_ls_shift/su_mean         0.0000217


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2691
_refine_ls_R_factor_all          0.0654
_refine_ls_wR_factor_all         0.0766

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2563
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_gt          0.0689

_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_abs_structure_details 'Flack (1983), 1161 Friedel-pairs'


_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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.347 0.325 0.140 0.362E-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 -0.0515(2) 0.0866(6) 0.7950(2) 0.0811 1.0000 Uani . . . . . .
C2 C 0.0148(3) 0.2494(9) 0.7563(3) 0.0622 1.0000 Uani . . . . . .
F3 F 0.0313(2) 0.4696(6) 0.8224(2) 0.0873 1.0000 Uani . . . . . .
N4 N 0.1269(3) 0.1410(7) 0.7610(3) 0.0614 1.0000 Uani . . . . . .
C5 C 0.2258(3) 0.2448(7) 0.8135(3) 0.0498 1.0000 Uani . . . . . .
C6 C 0.3369(3) 0.3247(6) 0.8639(2) 0.0377 1.0000 Uani . . . . . .
C7 C 0.4049(2) 0.5077(5) 0.8185(2) 0.0329 1.0000 Uani . . . . . .
C8 C 0.5385(2) 0.5038(5) 0.8574(2) 0.0306 1.0000 Uani . . . . . .
C9 C 0.6050(2) 0.6834(5) 0.8164(2) 0.0326 1.0000 Uani . . . . . .
C10 C 0.5369(3) 0.8620(5) 0.7321(2) 0.0332 1.0000 Uani . . . . . .
C11 C 0.4056(3) 0.8573(5) 0.6955(2) 0.0342 1.0000 Uani . . . . . .
C12 C 0.3431(3) 0.6789(5) 0.7416(2) 0.0343 1.0000 Uani . . . . . .
C13 C 0.3375(3) 1.0315(6) 0.6152(2) 0.0402 1.0000 Uani . . . . . .
C14 C 0.3983(3) 1.2047(6) 0.5722(2) 0.0469 1.0000 Uani . . . . . .
C15 C 0.5276(3) 1.2086(6) 0.6079(2) 0.0460 1.0000 Uani . . . . . .
C16 C 0.5957(3) 1.0435(6) 0.6861(2) 0.0417 1.0000 Uani . . . . . .
C17 C 0.7347(3) 0.6784(6) 0.8571(2) 0.0436 1.0000 Uani . . . . . .
C18 C 0.7983(3) 0.5057(7) 0.9348(3) 0.0481 1.0000 Uani . . . . . .
C19 C 0.7339(3) 0.3276(6) 0.9737(3) 0.0453 1.0000 Uani . . . . . .
C20 C 0.6073(3) 0.3253(6) 0.9362(2) 0.0381 1.0000 Uani . . . . . .
C21 C -0.0658(4) 0.3363(10) 0.6467(3) 0.0697 1.0000 Uani . . . . . .
F22 F -0.0052(3) 0.4892(8) 0.6045(3) 0.1138 1.0000 Uani . . . . . .
F23 F -0.1651(2) 0.4545(7) 0.6503(2) 0.1004 1.0000 Uani . . . . . .
F24 F -0.1026(4) 0.1350(9) 0.5829(3) 0.1267 1.0000 Uani . . . . . .
H61 H 0.3775 0.2664 0.9332 0.0449 1.0000 Uiso R . . . . .
H121 H 0.2572 0.6796 0.7174 0.0402 1.0000 Uiso R . . . . .
H131 H 0.2507 1.0234 0.5909 0.0479 1.0000 Uiso R . . . . .
H141 H 0.3519 1.3246 0.5211 0.0557 1.0000 Uiso R . . . . .
H151 H 0.5672 1.3266 0.5784 0.0561 1.0000 Uiso R . . . . .
H161 H 0.6833 1.0488 0.7101 0.0497 1.0000 Uiso R . . . . .
H171 H 0.7798 0.8006 0.8320 0.0519 1.0000 Uiso R . . . . .
H181 H 0.8853 0.5037 0.9623 0.0577 1.0000 Uiso R . . . . .
H191 H 0.7772 0.2059 1.0262 0.0541 1.0000 Uiso R . . . . .
H201 H 0.5651 0.2042 0.9615 0.0456 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3526(10)
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(4) yes
C2 . F3 . 1.415(5) yes
C2 . N4 . 1.384(5) yes
C2 . C21 . 1.502(6) yes
N4 . C5 . 1.236(5) yes
C5 . C6 . 1.291(5) yes
C6 . C7 . 1.479(4) yes
C6 . H61 . 0.928 no
C7 . C8 . 1.441(4) yes
C7 . C12 . 1.358(4) yes
C8 . C9 . 1.423(4) yes
C8 . C20 . 1.419(4) yes
C9 . C10 . 1.459(4) yes
C9 . C17 . 1.399(4) yes
C10 . C11 . 1.417(4) yes
C10 . C16 . 1.411(4) yes
C11 . C12 . 1.428(4) yes
C11 . C13 . 1.414(4) yes
C12 . H121 . 0.927 no
C13 . C14 . 1.374(5) yes
C13 . H131 . 0.938 no
C14 . C15 . 1.395(5) yes
C14 . H141 . 0.942 no
C15 . C16 . 1.368(5) yes
C15 . H151 . 0.925 no
C16 . H161 . 0.946 no
C17 . C18 . 1.374(5) yes
C17 . H171 . 0.948 no
C18 . C19 . 1.388(5) yes
C18 . H181 . 0.939 no
C19 . C20 . 1.365(5) yes
C19 . H191 . 0.947 no
C20 . H201 . 0.923 no
C21 . F22 . 1.299(5) yes
C21 . F23 . 1.308(5) yes
C21 . F24 . 1.321(6) 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 . 104.3(3) yes
F1 . C2 . N4 . 111.1(4) yes
F3 . C2 . N4 . 111.9(3) yes
F1 . C2 . C21 . 108.3(3) yes
F3 . C2 . C21 . 105.3(4) yes
N4 . C2 . C21 . 115.1(3) yes
C2 . N4 . C5 . 120.5(4) yes
N4 . C5 . C6 . 171.4(4) yes
C5 . C6 . C7 . 124.0(3) yes
C5 . C6 . H61 . 118.9 no
C7 . C6 . H61 . 117.1 no
C6 . C7 . C8 . 119.1(2) yes
C6 . C7 . C12 . 120.9(2) yes
C8 . C7 . C12 . 119.9(2) yes
C7 . C8 . C9 . 119.7(2) yes
C7 . C8 . C20 . 122.1(2) yes
C9 . C8 . C20 . 118.3(2) yes
C8 . C9 . C10 . 119.5(2) yes
C8 . C9 . C17 . 118.5(3) yes
C10 . C9 . C17 . 122.0(2) yes
C9 . C10 . C11 . 118.9(2) yes
C9 . C10 . C16 . 123.1(3) yes
C11 . C10 . C16 . 118.0(3) yes
C10 . C11 . C12 . 119.5(2) yes
C10 . C11 . C13 . 119.9(2) yes
C12 . C11 . C13 . 120.6(3) yes
C11 . C12 . C7 . 122.5(2) yes
C11 . C12 . H121 . 118.4 no
C7 . C12 . H121 . 119.1 no
C11 . C13 . C14 . 120.2(3) yes
C11 . C13 . H131 . 118.8 no
C14 . C13 . H131 . 121.0 no
C13 . C14 . C15 . 119.9(3) yes
C13 . C14 . H141 . 119.3 no
C15 . C14 . H141 . 120.7 no
C14 . C15 . C16 . 121.1(3) yes
C14 . C15 . H151 . 118.9 no
C16 . C15 . H151 . 120.0 no
C10 . C16 . C15 . 120.9(3) yes
C10 . C16 . H161 . 118.7 no
C15 . C16 . H161 . 120.4 no
C9 . C17 . C18 . 121.7(3) yes
C9 . C17 . H171 . 119.1 no
C18 . C17 . H171 . 119.1 no
C17 . C18 . C19 . 120.0(3) yes
C17 . C18 . H181 . 121.6 no
C19 . C18 . H181 . 118.4 no
C18 . C19 . C20 . 120.2(3) yes
C18 . C19 . H191 . 120.4 no
C20 . C19 . H191 . 119.4 no
C8 . C20 . C19 . 121.3(3) yes
C8 . C20 . H201 . 118.9 no
C19 . C20 . H201 . 119.7 no
C2 . C21 . F22 . 110.8(3) yes
C2 . C21 . F23 . 111.4(3) yes
F22 . C21 . F23 . 109.0(5) yes
C2 . C21 . F24 . 109.7(4) yes
F22 . C21 . F24 . 108.2(4) yes
F23 . C21 . F24 . 107.6(4) yes



####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2251500'
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             
;
2023-03-24 deposited with the CCDC.	2023-05-22 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                   9.3435(3)
_cell_length_b                   10.6287(4)
_cell_length_c                   11.0605(4)
_cell_angle_alpha                66.5847(13)
_cell_angle_beta                 85.0791(13)
_cell_angle_gamma                78.7344(13)
_cell_volume                     988.49(6)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .
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 0.0033 0.0016 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 0.0061 0.0033 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 0.0171 0.0103 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        
(E)-N-(perfluoroethyl)-2,3,4-triphenylcyclobut-2-en-1-imine
_chemical_formula_moiety         'C24 H16 F5 N'

# Given Formula = C24 H19 F5 N1 
# Dc =      1.40 Fooo =    424.00 Mu =      1.14 M =    416.41
# Found Formula = C24 H16 F5 N1 
# Dc =      1.39 FOOO =    424.00 Mu =      1.14 M =    413.39

_chemical_formula_sum            'C24 H16 F5 N'
_chemical_compound_source        ?
_chemical_formula_weight         413.39


_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      2.2826
_cell_measurement_theta_max      26.2799
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.021
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_max          0.081

_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.114

# Sheldrick geometric approximatio 0.99 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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            73711
_reflns_number_total             4532
_diffrn_reflns_av_R_equivalents  0.083
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4532 
# Theoretical number of reflections is about 9068 


_diffrn_reflns_theta_min         2.007
_diffrn_reflns_theta_max         27.483
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        27.483
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -11
_reflns_limit_h_max              12
_reflns_limit_k_min              -12
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   3.38
_oxford_diffrn_Wilson_scale      15.88

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

_refine_diff_density_min         -0.25
_refine_diff_density_max         0.21


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         2835
_refine_ls_number_restraints     0
_refine_ls_number_parameters     272
_oxford_refine_ls_R_factor_ref   0.0452
_refine_ls_wR_factor_ref         0.0407
_refine_ls_goodness_of_fit_ref   1.0615
_refine_ls_shift/su_max          0.0092702
_refine_ls_shift/su_mean         0.0006916


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4531
_refine_ls_R_factor_all          0.0847
_refine_ls_wR_factor_all         0.0836

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2835
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_gt          0.0407


_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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.236 0.210 0.114 
;

# 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 0.58661(11) 0.00009(11) 0.09746(11) 0.0489 1.0000 Uani . . . . . .
C2 C 0.70080(17) -0.02682(18) 0.17718(18) 0.0394 1.0000 Uani . . . . . .
F3 F 0.82248(11) -0.04423(11) 0.10333(11) 0.0522 1.0000 Uani . . . . . .
N4 N 0.71172(14) 0.07569(14) 0.22305(14) 0.0368 1.0000 Uani . . . . . .
C5 C 0.60858(17) 0.17952(17) 0.20585(16) 0.0343 1.0000 Uani . . . . . .
C6 C 0.59787(17) 0.29992(17) 0.24087(17) 0.0353 1.0000 Uani . . . . . .
C7 C 0.46382(17) 0.35611(17) 0.18431(16) 0.0357 1.0000 Uani . . . . . .
C8 C 0.45315(17) 0.23390(17) 0.14703(16) 0.0354 1.0000 Uani . . . . . .
C9 C 0.33755(16) 0.14836(17) 0.21878(16) 0.0340 1.0000 Uani . . . . . .
C10 C 0.23766(18) 0.12440(18) 0.14808(18) 0.0414 1.0000 Uani . . . . . .
C11 C 0.1304(2) 0.0475(2) 0.2136(2) 0.0519 1.0000 Uani . . . . . .
C12 C 0.1227(2) -0.0064(2) 0.3489(2) 0.0544 1.0000 Uani . . . . . .
C13 C 0.2216(2) 0.0168(2) 0.4198(2) 0.0518 1.0000 Uani . . . . . .
C14 C 0.32798(19) 0.09408(19) 0.35513(18) 0.0433 1.0000 Uani . . . . . .
C15 C 0.35925(18) 0.48457(17) 0.15937(17) 0.0403 1.0000 Uani . . . . . .
C16 C 0.3937(2) 0.59649(18) 0.18002(19) 0.0476 1.0000 Uani . . . . . .
C17 C 0.2910(2) 0.7170(2) 0.1560(2) 0.0592 1.0000 Uani . . . . . .
C18 C 0.1546(3) 0.7264(2) 0.1132(2) 0.0673 1.0000 Uani . . . . . .
C19 C 0.1195(2) 0.6185(2) 0.0903(3) 0.0730 1.0000 Uani . . . . . .
C20 C 0.2215(2) 0.4976(2) 0.1121(2) 0.0574 1.0000 Uani . . . . . .
C21 C 0.69914(18) 0.33364(16) 0.31342(17) 0.0368 1.0000 Uani . . . . . .
C22 C 0.6492(2) 0.38239(19) 0.41152(19) 0.0476 1.0000 Uani . . . . . .
C23 C 0.7464(3) 0.4076(2) 0.4826(2) 0.0625 1.0000 Uani . . . . . .
C24 C 0.8928(3) 0.3841(2) 0.4580(3) 0.0678 1.0000 Uani . . . . . .
C25 C 0.9445(2) 0.3354(2) 0.3617(2) 0.0633 1.0000 Uani . . . . . .
C26 C 0.84794(19) 0.30947(19) 0.2898(2) 0.0481 1.0000 Uani . . . . . .
C27 C 0.6968(2) -0.1689(2) 0.2869(2) 0.0543 1.0000 Uani . . . . . .
F28 F 0.81154(16) -0.20994(13) 0.36351(14) 0.0830 1.0000 Uani . . . . . .
F29 F 0.57820(16) -0.16422(15) 0.36117(14) 0.0826 1.0000 Uani . . . . . .
F30 F 0.69542(16) -0.26411(12) 0.23755(14) 0.0754 1.0000 Uani . . . . . .
H81 H 0.4497 0.2581 0.0536 0.0406 1.0000 Uiso R . . . . .
H101 H 0.2423 0.1633 0.0550 0.0487 1.0000 Uiso R . . . . .
H111 H 0.0620 0.0350 0.1626 0.0617 1.0000 Uiso R . . . . .
H121 H 0.0488 -0.0593 0.3946 0.0654 1.0000 Uiso R . . . . .
H131 H 0.2161 -0.0213 0.5138 0.0618 1.0000 Uiso R . . . . .
H141 H 0.3965 0.1122 0.4023 0.0519 1.0000 Uiso R . . . . .
H161 H 0.4872 0.5892 0.2123 0.0567 1.0000 Uiso R . . . . .
H171 H 0.3169 0.7903 0.1695 0.0716 1.0000 Uiso R . . . . .
H181 H 0.0844 0.8089 0.0995 0.0803 1.0000 Uiso R . . . . .
H191 H 0.0248 0.6245 0.0587 0.0861 1.0000 Uiso R . . . . .
H201 H 0.1944 0.4211 0.0976 0.0682 1.0000 Uiso R . . . . .
H221 H 0.5502 0.3950 0.4305 0.0562 1.0000 Uiso R . . . . .
H231 H 0.7118 0.4398 0.5479 0.0746 1.0000 Uiso R . . . . .
H241 H 0.9586 0.4002 0.5080 0.0809 1.0000 Uiso R . . . . .
H251 H 1.0432 0.3188 0.3454 0.0752 1.0000 Uiso R . . . . .
H261 H 0.8827 0.2755 0.2253 0.0578 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       160(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.2803(5)
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 . 1.3562(18) yes
C2 . F3 . 1.3685(19) yes
C2 . N4 . 1.395(2) yes
C2 . C27 . 1.520(3) yes
N4 . C5 . 1.277(2) yes
C5 . C6 . 1.461(2) yes
C5 . C8 . 1.550(2) yes
C6 . C7 . 1.365(2) yes
C6 . C21 . 1.469(2) yes
C7 . C8 . 1.533(2) yes
C7 . C15 . 1.456(2) yes
C8 . C9 . 1.512(2) yes
C8 . H81 . 0.963 no
C9 . C10 . 1.387(2) yes
C9 . C14 . 1.386(2) yes
C10 . C11 . 1.386(3) yes
C10 . H101 . 0.945 no
C11 . C12 . 1.375(3) yes
C11 . H111 . 0.949 no
C12 . C13 . 1.377(3) yes
C12 . H121 . 0.957 no
C13 . C14 . 1.380(3) yes
C13 . H131 . 0.955 no
C14 . H141 . 0.951 no
C15 . C16 . 1.396(3) yes
C15 . C20 . 1.392(3) yes
C16 . C17 . 1.387(3) yes
C16 . H161 . 0.950 no
C17 . C18 . 1.369(3) yes
C17 . H171 . 0.928 no
C18 . C19 . 1.370(4) yes
C18 . H181 . 0.954 no
C19 . C20 . 1.390(3) yes
C19 . H191 . 0.960 no
C20 . H201 . 0.971 no
C21 . C22 . 1.389(2) yes
C21 . C26 . 1.385(2) yes
C22 . C23 . 1.379(3) yes
C22 . H221 . 0.926 no
C23 . C24 . 1.365(3) yes
C23 . H231 . 0.926 no
C24 . C25 . 1.375(3) yes
C24 . H241 . 0.942 no
C25 . C26 . 1.384(3) yes
C25 . H251 . 0.921 no
C26 . H261 . 0.930 no
C27 . F28 . 1.318(2) yes
C27 . F29 . 1.327(3) yes
C27 . F30 . 1.330(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 . 105.08(13) yes
F1 . C2 . N4 . 116.50(14) yes
F3 . C2 . N4 . 108.64(13) yes
F1 . C2 . C27 . 106.66(14) yes
F3 . C2 . C27 . 105.79(14) yes
N4 . C2 . C27 . 113.36(15) yes
C2 . N4 . C5 . 121.11(14) yes
N4 . C5 . C6 . 130.62(15) yes
N4 . C5 . C8 . 138.73(15) yes
C6 . C5 . C8 . 90.66(12) yes
C5 . C6 . C7 . 91.72(13) yes
C5 . C6 . C21 . 130.42(14) yes
C7 . C6 . C21 . 137.83(15) yes
C6 . C7 . C8 . 95.16(13) yes
C6 . C7 . C15 . 136.48(16) yes
C8 . C7 . C15 . 128.35(15) yes
C7 . C8 . C5 . 82.32(12) yes
C7 . C8 . C9 . 116.21(13) yes
C5 . C8 . C9 . 116.39(14) yes
C7 . C8 . H81 . 114.0 no
C5 . C8 . H81 . 114.4 no
C9 . C8 . H81 . 110.9 no
C8 . C9 . C10 . 120.03(15) yes
C8 . C9 . C14 . 121.12(15) yes
C10 . C9 . C14 . 118.84(16) yes
C9 . C10 . C11 . 120.13(18) yes
C9 . C10 . H101 . 119.1 no
C11 . C10 . H101 . 120.8 no
C10 . C11 . C12 . 120.41(18) yes
C10 . C11 . H111 . 118.2 no
C12 . C11 . H111 . 121.3 no
C11 . C12 . C13 . 119.81(18) yes
C11 . C12 . H121 . 120.7 no
C13 . C12 . H121 . 119.5 no
C12 . C13 . C14 . 120.06(19) yes
C12 . C13 . H131 . 119.5 no
C14 . C13 . H131 . 120.4 no
C9 . C14 . C13 . 120.75(17) yes
C9 . C14 . H141 . 117.9 no
C13 . C14 . H141 . 121.3 no
C7 . C15 . C16 . 121.85(16) yes
C7 . C15 . C20 . 119.44(16) yes
C16 . C15 . C20 . 118.70(16) yes
C15 . C16 . C17 . 120.28(19) yes
C15 . C16 . H161 . 119.7 no
C17 . C16 . H161 . 120.0 no
C16 . C17 . C18 . 120.2(2) yes
C16 . C17 . H171 . 118.6 no
C18 . C17 . H171 . 121.2 no
C17 . C18 . C19 . 120.38(19) yes
C17 . C18 . H181 . 119.2 no
C19 . C18 . H181 . 120.4 no
C18 . C19 . C20 . 120.3(2) yes
C18 . C19 . H191 . 121.2 no
C20 . C19 . H191 . 118.5 no
C15 . C20 . C19 . 120.1(2) yes
C15 . C20 . H201 . 120.4 no
C19 . C20 . H201 . 119.5 no
C6 . C21 . C22 . 121.08(16) yes
C6 . C21 . C26 . 120.03(16) yes
C22 . C21 . C26 . 118.79(16) yes
C21 . C22 . C23 . 120.28(19) yes
C21 . C22 . H221 . 119.3 no
C23 . C22 . H221 . 120.4 no
C22 . C23 . C24 . 120.5(2) yes
C22 . C23 . H231 . 119.4 no
C24 . C23 . H231 . 120.1 no
C23 . C24 . C25 . 120.14(19) yes
C23 . C24 . H241 . 119.9 no
C25 . C24 . H241 . 120.0 no
C24 . C25 . C26 . 120.0(2) yes
C24 . C25 . H251 . 120.3 no
C26 . C25 . H251 . 119.8 no
C21 . C26 . C25 . 120.37(19) yes
C21 . C26 . H261 . 119.6 no
C25 . C26 . H261 . 120.1 no
C2 . C27 . F28 . 111.21(16) yes
C2 . C27 . F29 . 110.39(16) yes
F28 . C27 . F29 . 107.98(19) yes
C2 . C27 . F30 . 110.77(17) yes
F28 . C27 . F30 . 108.05(17) yes
F29 . C27 . F30 . 108.33(17) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-1 0 2 x .

