# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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 2361590'
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             
;
2024-08-02 deposited with the CCDC.	2024-08-12 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                   18.7156(7)
_cell_length_b                   8.5123(3)
_cell_length_c                   21.5158(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3427.7(2)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,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        
6,6-difluoro-4-(4-methoxyphenyl)-5-(p-tolyl)-2-(trifluoromethyl)-6H-1,3-oxazine
_chemical_formula_moiety         'C19 H14 F5 N O2'

# Given Formula = C19 H14 F5 N1 O2 
# Dc =      1.49 Fooo =   1568.00 Mu =     11.64 M =    383.32
# Found Formula = C19 H14 F5 N1 O2 
# Dc =      1.49 FOOO =   1568.00 Mu =     11.64 M =    383.32

_chemical_formula_sum            'C19 H14 F5 N O2'
_chemical_compound_source        .
_chemical_formula_weight         383.32


_cell_measurement_reflns_used    9323
_cell_measurement_theta_min      4.1094
_cell_measurement_theta_max      72.2033
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.080
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_max          0.516

_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1568
_exptl_absorpt_coefficient_mu    1.164

# Sheldrick geometric approximatio 0.86 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.91
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            46820
_diffrn_reflns_av_unetI/netI     0.071
_reflns_number_total             3381
_diffrn_reflns_av_R_equivalents  0.047
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3381 
# Theoretical number of reflections is about 6777 


_diffrn_reflns_theta_min         4.109
_diffrn_reflns_theta_max         72.321
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        72.321
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              0
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              26

_oxford_diffrn_Wilson_B_factor   3.12
_oxford_diffrn_Wilson_scale      68.56

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

_refine_diff_density_min         -0.44
_refine_diff_density_max         0.51


# 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>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3380
_refine_ls_R_factor_ref          0.0451
_refine_ls_wR_factor_ref         0.1098
_refine_ls_goodness_of_fit_ref   0.9901
_refine_ls_shift/su_max          0.0004765
_refine_ls_shift/su_mean         0.0000679


# Computed with I/sigma = -10 
_reflns_number_all               3381
_refine_ls_R_factor_all          0.0452
_refine_ls_wR_factor_all         0.1099

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2934
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_gt          0.1033


_refine_ls_structure_factor_coef Fsqd
_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= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.96P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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 0.48563(6) 0.67569(13) 0.72235(5) 0.0480 1.0000 Uani . . . . . .
C2 C 0.48468(8) 0.58829(18) 0.66955(7) 0.0332 1.0000 Uani . . . . . .
F3 F 0.50815(5) 0.44491(12) 0.68819(5) 0.0432 1.0000 Uani . . . . . .
O4 O 0.41303(6) 0.56995(16) 0.65480(6) 0.0444 1.0000 Uani . . . . . .
C5 C 0.39201(8) 0.59928(18) 0.59568(8) 0.0350 1.0000 Uani . . . . . .
N6 N 0.42829(7) 0.65322(15) 0.55178(6) 0.0317 1.0000 Uani . . . . . .
C7 C 0.50031(8) 0.69290(16) 0.56472(7) 0.0275 1.0000 Uani . . . . . .
C8 C 0.53036(8) 0.65619(17) 0.62002(7) 0.0288 1.0000 Uani . . . . . .
C9 C 0.60816(8) 0.66783(17) 0.63416(7) 0.0284 1.0000 Uani . . . . . .
C10 C 0.63467(9) 0.75513(19) 0.68385(7) 0.0344 1.0000 Uani . . . . . .
C11 C 0.70771(9) 0.7637(2) 0.69424(8) 0.0388 1.0000 Uani . . . . . .
C12 C 0.75609(9) 0.68544(19) 0.65659(8) 0.0376 1.0000 Uani . . . . . .
C13 C 0.72930(9) 0.5973(2) 0.60740(8) 0.0380 1.0000 Uani . . . . . .
C14 C 0.65641(8) 0.58830(19) 0.59622(7) 0.0339 1.0000 Uani . . . . . .
C15 C 0.83552(10) 0.6956(2) 0.66834(11) 0.0542 1.0000 Uani . . . . . .
C16 C 0.53583(7) 0.77956(16) 0.51390(6) 0.0269 1.0000 Uani . . . . . .
C17 C 0.58516(8) 0.89846(17) 0.52682(7) 0.0289 1.0000 Uani . . . . . .
C18 C 0.61577(8) 0.98511(17) 0.47985(7) 0.0302 1.0000 Uani . . . . . .
C19 C 0.59804(8) 0.95471(17) 0.41816(7) 0.0293 1.0000 Uani . . . . . .
O20 O 0.63079(6) 1.04858(14) 0.37541(5) 0.0380 1.0000 Uani . . . . . .
C21 C 0.62368(13) 1.0070(3) 0.31184(8) 0.0555 1.0000 Uani . . . . . .
C22 C 0.54895(8) 0.83761(18) 0.40416(7) 0.0329 1.0000 Uani . . . . . .
C23 C 0.51775(8) 0.75239(18) 0.45204(7) 0.0315 1.0000 Uani . . . . . .
C24 C 0.31354(9) 0.5582(2) 0.58871(10) 0.0461 1.0000 Uani . . . . . .
F25 F 0.27564(6) 0.62152(17) 0.63410(6) 0.0645 1.0000 Uani . . . . . .
F26 F 0.28730(6) 0.61491(19) 0.53626(6) 0.0705 1.0000 Uani . . . . . .
F27 F 0.30382(7) 0.40634(15) 0.58938(11) 0.1026 1.0000 Uani . . . . . .
H101 H 0.6025 0.8114 0.7101 0.0403 1.0000 Uiso R . . . . .
H111 H 0.7247 0.8251 0.7276 0.0478 1.0000 Uiso R . . . . .
H131 H 0.7610 0.5393 0.5818 0.0469 1.0000 Uiso R . . . . .
H141 H 0.6386 0.5265 0.5627 0.0407 1.0000 Uiso R . . . . .
H152 H 0.8639 0.6489 0.6363 0.0821 1.0000 Uiso R . . . . .
H151 H 0.8473 0.6430 0.7069 0.0826 1.0000 Uiso R . . . . .
H153 H 0.8504 0.8018 0.6729 0.0810 1.0000 Uiso R . . . . .
H171 H 0.5957 0.9218 0.5693 0.0354 1.0000 Uiso R . . . . .
H181 H 0.6484 1.0670 0.4888 0.0356 1.0000 Uiso R . . . . .
H211 H 0.6537 1.0779 0.2884 0.0819 1.0000 Uiso R . . . . .
H212 H 0.6390 0.8976 0.3054 0.0817 1.0000 Uiso R . . . . .
H213 H 0.5749 1.0190 0.3000 0.0810 1.0000 Uiso R . . . . .
H221 H 0.5358 0.8146 0.3624 0.0400 1.0000 Uiso R . . . . .
H231 H 0.4835 0.6751 0.4418 0.0385 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       64(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.12223(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 . 1.3580(19) yes
C2 . F3 . 1.3578(18) yes
C2 . O4 . 1.3867(19) yes
C2 . C8 . 1.483(2) yes
O4 . C5 . 1.355(2) yes
C5 . N6 . 1.251(2) yes
C5 . C24 . 1.517(2) yes
N6 . C7 . 1.4171(18) yes
C7 . C8 . 1.353(2) yes
C7 . C16 . 1.477(2) yes
C8 . C9 . 1.491(2) yes
C9 . C10 . 1.393(2) yes
C9 . C14 . 1.393(2) yes
C10 . C11 . 1.387(2) yes
C10 . H101 . 0.954 no
C11 . C12 . 1.386(2) yes
C11 . H111 . 0.943 no
C12 . C13 . 1.391(2) yes
C12 . C15 . 1.510(2) yes
C13 . C14 . 1.387(2) yes
C13 . H131 . 0.947 no
C14 . H141 . 0.954 no
C15 . H152 . 0.955 no
C15 . H151 . 0.968 no
C15 . H153 . 0.951 no
C16 . C17 . 1.398(2) yes
C16 . C23 . 1.393(2) yes
C17 . C18 . 1.376(2) yes
C17 . H171 . 0.956 no
C18 . C19 . 1.392(2) yes
C18 . H181 . 0.947 no
C19 . O20 . 1.3640(18) yes
C19 . C22 . 1.389(2) yes
O20 . C21 . 1.419(2) yes
C21 . H211 . 0.967 no
C21 . H212 . 0.984 no
C21 . H213 . 0.953 no
C22 . C23 . 1.389(2) yes
C22 . H221 . 0.951 no
C23 . H231 . 0.945 no
C24 . F25 . 1.322(2) yes
C24 . F26 . 1.322(2) yes
C24 . F27 . 1.306(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 . 103.95(12) yes
F1 . C2 . O4 . 105.41(13) yes
F3 . C2 . O4 . 106.21(12) yes
F1 . C2 . C8 . 112.33(13) yes
F3 . C2 . C8 . 112.08(13) yes
O4 . C2 . C8 . 115.90(13) yes
C2 . O4 . C5 . 118.36(12) yes
O4 . C5 . N6 . 128.25(14) yes
O4 . C5 . C24 . 109.36(14) yes
N6 . C5 . C24 . 122.38(16) yes
C5 . N6 . C7 . 117.10(14) yes
N6 . C7 . C8 . 120.87(14) yes
N6 . C7 . C16 . 113.69(12) yes
C8 . C7 . C16 . 125.41(13) yes
C2 . C8 . C7 . 118.84(13) yes
C2 . C8 . C9 . 116.25(13) yes
C7 . C8 . C9 . 124.76(13) yes
C8 . C9 . C10 . 122.66(14) yes
C8 . C9 . C14 . 118.77(13) yes
C10 . C9 . C14 . 118.57(14) yes
C9 . C10 . C11 . 120.17(15) yes
C9 . C10 . H101 . 119.9 no
C11 . C10 . H101 . 119.9 no
C10 . C11 . C12 . 121.63(15) yes
C10 . C11 . H111 . 118.9 no
C12 . C11 . H111 . 119.4 no
C11 . C12 . C13 . 117.95(15) yes
C11 . C12 . C15 . 121.19(16) yes
C13 . C12 . C15 . 120.86(16) yes
C12 . C13 . C14 . 121.07(16) yes
C12 . C13 . H131 . 119.8 no
C14 . C13 . H131 . 119.1 no
C9 . C14 . C13 . 120.61(15) yes
C9 . C14 . H141 . 119.1 no
C13 . C14 . H141 . 120.3 no
C12 . C15 . H152 . 113.7 no
C12 . C15 . H151 . 110.0 no
H152 . C15 . H151 . 107.4 no
C12 . C15 . H153 . 111.1 no
H152 . C15 . H153 . 107.8 no
H151 . C15 . H153 . 106.5 no
C7 . C16 . C17 . 120.77(13) yes
C7 . C16 . C23 . 121.01(13) yes
C17 . C16 . C23 . 118.09(14) yes
C16 . C17 . C18 . 121.12(13) yes
C16 . C17 . H171 . 118.5 no
C18 . C17 . H171 . 120.3 no
C17 . C18 . C19 . 120.09(14) yes
C17 . C18 . H181 . 120.9 no
C19 . C18 . H181 . 119.0 no
C18 . C19 . O20 . 115.27(13) yes
C18 . C19 . C22 . 119.86(14) yes
O20 . C19 . C22 . 124.86(14) yes
C19 . O20 . C21 . 117.49(14) yes
O20 . C21 . H211 . 107.1 no
O20 . C21 . H212 . 110.2 no
H211 . C21 . H212 . 110.4 no
O20 . C21 . H213 . 108.6 no
H211 . C21 . H213 . 110.5 no
H212 . C21 . H213 . 110.0 no
C19 . C22 . C23 . 119.49(14) yes
C19 . C22 . H221 . 121.6 no
C23 . C22 . H221 . 119.0 no
C16 . C23 . C22 . 121.34(14) yes
C16 . C23 . H231 . 120.2 no
C22 . C23 . H231 . 118.5 no
C5 . C24 . F25 . 110.65(15) yes
C5 . C24 . F26 . 111.10(15) yes
F25 . C24 . F26 . 106.41(16) yes
C5 . C24 . F27 . 111.22(15) yes
F25 . C24 . F27 . 108.71(18) yes
F26 . C24 . F27 . 108.60(18) yes



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# 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 2361631'
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             
;
2024-08-02 deposited with the CCDC.	2024-08-12 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                   4.8502(2)
_cell_length_b                   10.1006(3)
_cell_length_c                   14.4402(5)
_cell_angle_alpha                109.3028(12)
_cell_angle_beta                 97.3122(13)
_cell_angle_gamma                95.9100(13)
_cell_volume                     654.23(4)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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        
2-fluoro-8-methoxy-2-methyl-5-(trifluoromethyl)-2,3-dihydro-1H-cyclopenta[c]isoquinolin-1-one
_chemical_formula_moiety         'C15 H11 F4 N O2'

# Given Formula = C15 H11 F4 N1 O2 
# Dc =      1.59 Fooo =    320.00 Mu =     12.62 M =    313.25
# Found Formula = C15 H11 F4 N1 O2 
# Dc =      1.59 FOOO =    320.00 Mu =     12.62 M =    313.25

_chemical_formula_sum            'C15 H11 F4 N O2'
_chemical_compound_source        .
_chemical_formula_weight         313.25


_cell_measurement_reflns_used    8520
_cell_measurement_theta_min      3.2918
_cell_measurement_theta_max      70.0945
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.046
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_max          0.358

_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    1.262

# Sheldrick geometric approximatio 0.94 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.85
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            10818
_diffrn_reflns_av_unetI/netI     0.032
_reflns_number_total             2461
_diffrn_reflns_av_R_equivalents  0.018
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2461 
# Theoretical number of reflections is about 4972 


_diffrn_reflns_theta_min         3.292
_diffrn_reflns_theta_max         70.088
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        70.088
_diffrn_measured_fraction_theta_full 0.994


_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -5
_reflns_limit_h_max              5
_reflns_limit_k_min              -12
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.24
_oxford_diffrn_Wilson_scale      5.14

_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         0.29


# 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>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2461
_refine_ls_R_factor_ref          0.0355
_refine_ls_wR_factor_ref         0.0963
_refine_ls_goodness_of_fit_ref   0.9780
_refine_ls_shift/su_max          0.0007588
_refine_ls_shift/su_mean         0.0000678


# Computed with I/sigma = -10 
_reflns_number_all               2461
_refine_ls_R_factor_all          0.0355
_refine_ls_wR_factor_all         0.0963

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2292
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_gt          0.0929


_refine_ls_structure_factor_coef Fsqd
_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= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.24P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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 0.07357(15) 0.11840(8) 0.75533(6) 0.0318 1.0000 Uani . . . . . .
C2 C 0.3607(2) 0.17174(13) 0.79207(9) 0.0228 1.0000 Uani . . . . . .
C3 C 0.4859(3) 0.06705(14) 0.83253(10) 0.0299 1.0000 Uani . . . . . .
C4 C 0.4980(2) 0.18341(13) 0.70348(9) 0.0219 1.0000 Uani . . . . . .
O5 O 0.4696(2) 0.08894(9) 0.62392(7) 0.0298 1.0000 Uani . . . . . .
C6 C 0.6600(2) 0.32740(12) 0.73659(9) 0.0208 1.0000 Uani . . . . . .
C7 C 0.6000(2) 0.40586(13) 0.82747(9) 0.0214 1.0000 Uani . . . . . .
C8 C 0.3970(3) 0.32340(13) 0.86667(9) 0.0257 1.0000 Uani . . . . . .
N9 N 0.7097(2) 0.54378(11) 0.87821(8) 0.0240 1.0000 Uani . . . . . .
C10 C 0.8866(2) 0.60188(13) 0.83517(9) 0.0226 1.0000 Uani . . . . . .
C11 C 0.9950(3) 0.75823(14) 0.89193(10) 0.0278 1.0000 Uani . . . . . .
F12 F 0.9182(2) 0.83761(8) 0.83752(7) 0.0427 1.0000 Uani . . . . . .
F13 F 1.27654(17) 0.78530(9) 0.91421(6) 0.0370 1.0000 Uani . . . . . .
F14 F 0.89965(19) 0.80728(9) 0.97706(7) 0.0430 1.0000 Uani . . . . . .
C15 C 0.9746(2) 0.53246(12) 0.74315(9) 0.0214 1.0000 Uani . . . . . .
C16 C 0.8545(2) 0.38758(12) 0.69019(9) 0.0204 1.0000 Uani . . . . . .
C17 C 0.9343(2) 0.31012(13) 0.59961(9) 0.0227 1.0000 Uani . . . . . .
C18 C 1.1350(3) 0.37639(13) 0.56304(9) 0.0238 1.0000 Uani . . . . . .
O19 O 1.2355(2) 0.31383(10) 0.47876(7) 0.0298 1.0000 Uani . . . . . .
C20 C 1.1237(3) 0.16773(15) 0.42233(11) 0.0349 1.0000 Uani . . . . . .
C21 C 1.2558(3) 0.52081(14) 0.61454(10) 0.0266 1.0000 Uani . . . . . .
C22 C 1.1776(3) 0.59698(13) 0.70140(10) 0.0253 1.0000 Uani . . . . . .
H31 H 0.6799 0.0992 0.8575 0.0436 1.0000 Uiso R . . . . .
H33 H 0.3987 0.0584 0.8875 0.0424 1.0000 Uiso R . . . . .
H32 H 0.4668 -0.0237 0.7802 0.0422 1.0000 Uiso R . . . . .
H82 H 0.4750 0.3286 0.9338 0.0306 1.0000 Uiso R . . . . .
H81 H 0.2153 0.3589 0.8659 0.0295 1.0000 Uiso R . . . . .
H171 H 0.8542 0.2147 0.5673 0.0298 1.0000 Uiso R . . . . .
H203 H 1.2105 0.1424 0.3658 0.0532 1.0000 Uiso R . . . . .
H201 H 1.1636 0.1129 0.4629 0.0500 1.0000 Uiso R . . . . .
H202 H 0.9187 0.1569 0.3999 0.0514 1.0000 Uiso R . . . . .
H211 H 1.3919 0.5581 0.5864 0.0315 1.0000 Uiso R . . . . .
H221 H 1.2570 0.6931 0.7337 0.0321 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4462(9)
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 . 1.4072(14) yes
C2 . C3 . 1.5093(17) yes
C2 . C4 . 1.5473(17) yes
C2 . C8 . 1.5307(17) yes
C3 . H31 . 0.946 no
C3 . H33 . 0.970 no
C3 . H32 . 0.962 no
C4 . O5 . 1.2072(15) yes
C4 . C6 . 1.4733(16) yes
C6 . C7 . 1.3757(17) yes
C6 . C16 . 1.4214(16) yes
C7 . C8 . 1.5058(16) yes
C7 . N9 . 1.3542(16) yes
C8 . H82 . 0.977 no
C8 . H81 . 0.985 no
N9 . C10 . 1.3190(16) yes
C10 . C11 . 1.5185(17) yes
C10 . C15 . 1.4247(17) yes
C11 . F12 . 1.3424(16) yes
C11 . F13 . 1.3404(15) yes
C11 . F14 . 1.3264(16) yes
C15 . C16 . 1.4272(16) yes
C15 . C22 . 1.4269(17) yes
C16 . C17 . 1.4097(17) yes
C17 . C18 . 1.3803(17) yes
C17 . H171 . 0.937 no
C18 . O19 . 1.3505(15) yes
C18 . C21 . 1.4212(18) yes
O19 . C20 . 1.4365(17) yes
C20 . H203 . 0.939 no
C20 . H201 . 0.947 no
C20 . H202 . 0.989 no
C21 . C22 . 1.3609(19) yes
C21 . H211 . 0.927 no
C22 . H221 . 0.941 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 . C3 . 107.55(10) yes
F1 . C2 . C4 . 107.29(10) yes
C3 . C2 . C4 . 110.65(10) yes
F1 . C2 . C8 . 110.35(9) yes
C3 . C2 . C8 . 114.99(11) yes
C4 . C2 . C8 . 105.78(9) yes
C2 . C3 . H31 . 109.9 no
C2 . C3 . H33 . 111.0 no
H31 . C3 . H33 . 107.0 no
C2 . C3 . H32 . 110.0 no
H31 . C3 . H32 . 107.9 no
H33 . C3 . H32 . 111.0 no
C2 . C4 . O5 . 124.17(11) yes
C2 . C4 . C6 . 106.77(10) yes
O5 . C4 . C6 . 129.07(11) yes
C4 . C6 . C7 . 109.03(10) yes
C4 . C6 . C16 . 130.15(11) yes
C7 . C6 . C16 . 120.81(11) yes
C6 . C7 . C8 . 113.42(10) yes
C6 . C7 . N9 . 124.34(11) yes
C8 . C7 . N9 . 122.25(11) yes
C2 . C8 . C7 . 103.47(10) yes
C2 . C8 . H82 . 111.5 no
C7 . C8 . H82 . 110.8 no
C2 . C8 . H81 . 109.9 no
C7 . C8 . H81 . 110.3 no
H82 . C8 . H81 . 110.7 no
C7 . N9 . C10 . 115.53(10) yes
N9 . C10 . C11 . 114.00(11) yes
N9 . C10 . C15 . 126.18(11) yes
C11 . C10 . C15 . 119.80(11) yes
C10 . C11 . F12 . 110.93(11) yes
C10 . C11 . F13 . 112.25(10) yes
F12 . C11 . F13 . 106.36(11) yes
C10 . C11 . F14 . 112.94(11) yes
F12 . C11 . F14 . 107.13(11) yes
F13 . C11 . F14 . 106.86(11) yes
C10 . C15 . C16 . 117.50(11) yes
C10 . C15 . C22 . 124.55(11) yes
C16 . C15 . C22 . 117.95(11) yes
C15 . C16 . C6 . 115.60(11) yes
C15 . C16 . C17 . 121.17(11) yes
C6 . C16 . C17 . 123.20(11) yes
C16 . C17 . C18 . 118.77(11) yes
C16 . C17 . H171 . 119.1 no
C18 . C17 . H171 . 122.1 no
C17 . C18 . O19 . 124.90(11) yes
C17 . C18 . C21 . 120.80(11) yes
O19 . C18 . C21 . 114.30(11) yes
C18 . O19 . C20 . 117.70(10) yes
O19 . C20 . H203 . 106.6 no
O19 . C20 . H201 . 108.5 no
H203 . C20 . H201 . 112.3 no
O19 . C20 . H202 . 110.4 no
H203 . C20 . H202 . 108.2 no
H201 . C20 . H202 . 110.8 no
C18 . C21 . C22 . 120.86(11) yes
C18 . C21 . H211 . 116.2 no
C22 . C21 . H211 . 122.9 no
C15 . C22 . C21 . 120.44(11) yes
C15 . C22 . H221 . 119.9 no
C21 . C22 . H221 . 119.6 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
C17 . H171 . O5 . 124 0.94 2.52 3.1427(19) yes
C21 . H211 . O19 2_866 174 0.93 2.57 3.4898(19) yes



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# 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 2361632'
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             
;
2024-08-02 deposited with the CCDC.	2024-08-12 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                   11.2617(4)
_cell_length_b                   14.3039(5)
_cell_length_c                   9.1250(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.1605(11)
_cell_angle_gamma                90
_cell_volume                     1388.48(8)
_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'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4
_chemical_name_systematic        
5-phenyl-4-(thiophen-2-yl)-2-(trifluoromethyl)-6H-1,3-oxazin-6-one
_chemical_formula_moiety         'C15 H8 F3 N O2 S'

# Given Formula = C15 H8 F3 N1 O2 S1 
# Dc =      1.55 Fooo =    656.00 Mu =     24.77 M =    323.29
# Found Formula = C15 H8 F3 N1 O2 S1 
# Dc =      1.55 FOOO =    656.00 Mu =     24.77 M =    323.29

_chemical_formula_sum            'C15 H8 F3 N O2 S'
_chemical_compound_source        .
_chemical_formula_weight         323.29


_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      4.1558
_cell_measurement_theta_max      70.0287
_cell_measurement_temperature    180

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.516
_exptl_crystal_size_max          0.572

_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    2.477

# Sheldrick geometric approximatio 0.28 0.93 
_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  0.93
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            32093
_diffrn_reflns_av_unetI/netI     0.048
_reflns_number_total             2637
_diffrn_reflns_av_R_equivalents  0.033
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2637 
# Theoretical number of reflections is about 5275 


_diffrn_reflns_theta_min         4.156
_diffrn_reflns_theta_max         70.075
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        70.075
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -13
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   2.37
_oxford_diffrn_Wilson_scale      26.91

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

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.23


# 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>-3.0\s(I)
_refine_ls_number_restraints     14
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2637
_refine_ls_R_factor_ref          0.0298
_refine_ls_wR_factor_ref         0.0738
_refine_ls_goodness_of_fit_ref   0.9336
_refine_ls_shift/su_max          0.0004784
_refine_ls_shift/su_mean         0.0000485


# Computed with I/sigma = -10 
_reflns_number_all               2637
_refine_ls_R_factor_all          0.0298
_refine_ls_wR_factor_all         0.0738

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2497
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_gt          0.0719


_refine_ls_structure_factor_coef Fsqd
_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= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.55P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
C2 C 0.37178(11) 0.60374(8) 0.42181(13) 0.0249 1.0000 Uani . U . . . .
C6 C 0.45441(11) 0.62210(8) 0.33168(13) 0.0237 1.0000 Uani . . . . . .
N7 N 0.57731(9) 0.64436(7) 0.42595(11) 0.0264 1.0000 Uani . . . . . .
C8 C 0.65559(11) 0.66284(8) 0.35807(14) 0.0270 1.0000 Uani . . . . . .
O9 O 0.63778(8) 0.66293(7) 0.20528(10) 0.0319 1.0000 Uani . . . . . .
C10 C 0.51727(11) 0.64052(9) 0.10251(14) 0.0288 1.0000 Uani . . . . . .
C11 C 0.42258(11) 0.62006(8) 0.17368(13) 0.0242 1.0000 Uani . . . . . .
C12 C 0.29508(11) 0.59970(8) 0.06289(13) 0.0241 1.0000 Uani . . . . . .
C13 C 0.25581(12) 0.50846(9) 0.02201(14) 0.0293 1.0000 Uani . . . . . .
C14 C 0.13724(13) 0.49189(9) -0.08425(15) 0.0350 1.0000 Uani . . . . . .
C15 C 0.05840(12) 0.56538(10) -0.15029(16) 0.0378 1.0000 Uani . . . . . .
C16 C 0.09753(13) 0.65612(10) -0.11061(17) 0.0398 1.0000 Uani . . . . . .
C17 C 0.21552(12) 0.67341(9) -0.00478(16) 0.0333 1.0000 Uani . . . . . .
O18 O 0.50597(9) 0.64076(8) -0.03272(10) 0.0407 1.0000 Uani . . . . . .
C19 C 0.78818(12) 0.69375(10) 0.44877(15) 0.0337 1.0000 Uani . . . . . .
F20 F 0.80383(8) 0.78335(6) 0.42216(12) 0.0529 1.0000 Uani . . . . . .
F21 F 0.81344(8) 0.68251(8) 0.59902(10) 0.0553 1.0000 Uani . . . . . .
F22 F 0.87327(7) 0.64614(7) 0.40684(11) 0.0501 1.0000 Uani . . . . . .
H131 H 0.3103 0.4589 0.0671 0.0341 1.0000 Uiso R . . . . .
H141 H 0.1098 0.4309 -0.1098 0.0415 1.0000 Uiso R . . . . .
H151 H -0.0214 0.5539 -0.2213 0.0448 1.0000 Uiso R . . . . .
H161 H 0.0445 0.7067 -0.1573 0.0481 1.0000 Uiso R . . . . .
H171 H 0.2417 0.7341 0.0250 0.0408 1.0000 Uiso R . . . . .
C3 C 0.29865(13) 0.58353(9) 0.64443(15) 0.0330 1.0000 Uani . U . . . .
C1 C 0.20313(13) 0.56986(9) 0.50929(16) 0.0360 1.0000 Uani . . . . . .
S10 S 0.43694(6) 0.61137(5) 0.62109(6) 0.0264 0.827(2) Uani . . P 1 2 .
C4 C 0.4043(13) 0.6016(11) 0.5836(18) 0.0423 0.173(2) Uani . U P 1 1 .
C40 C 0.2460(5) 0.5820(5) 0.3802(7) 0.0374 0.827(2) Uani . . P 1 2 .
S41 S 0.2172(7) 0.5796(7) 0.3477(9) 0.0354 0.173(2) Uani . . P 1 1 .
H31 H 0.2995 0.5877 0.7469 0.0381 0.173(2) Uiso R . P 1 1 .
H32 H 0.2900 0.5789 0.7434 0.0390 0.827(2) Uiso R . P 1 2 .
H11 H 0.1255 0.5512 0.5153 0.0430 0.173(2) Uiso R . P 1 1 .
H12 H 0.1193 0.5565 0.5015 0.0429 0.827(2) Uiso R . P 1 2 .
H41 H 0.4868 0.5961 0.6480 0.0430 0.173(2) Uiso R . P 1 1 .
H401 H 0.1908 0.5712 0.2706 0.0384 0.827(2) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.20519(14)
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
C2 . C6 . 1.4538(16) yes
C2 . C4 . 1.400(16) yes
C2 . S41 . 1.684(8) yes
C2 . C6 . 1.4538(16) yes
C2 . S10 . 1.7266(12) yes
C2 . C40 . 1.376(6) yes
C6 . N7 . 1.4055(15) yes
C6 . C11 . 1.3671(16) yes
N7 . C8 . 1.2606(16) yes
C8 . O9 . 1.3418(15) yes
C8 . C19 . 1.5163(17) yes
O9 . C10 . 1.4102(14) yes
C10 . C11 . 1.4488(17) yes
C10 . O18 . 1.1983(15) yes
C11 . C12 . 1.4885(16) yes
C12 . C13 . 1.3891(17) yes
C12 . C17 . 1.3902(17) yes
C13 . C14 . 1.3891(18) yes
C13 . H131 . 0.940 no
C14 . C15 . 1.380(2) yes
C14 . H141 . 0.929 no
C15 . C16 . 1.380(2) yes
C15 . H151 . 0.934 no
C16 . C17 . 1.3846(18) yes
C16 . H161 . 0.946 no
C17 . H171 . 0.928 no
C19 . F20 . 1.3268(16) yes
C19 . F21 . 1.3155(16) yes
C19 . F22 . 1.3300(15) yes
C3 . C1 . 1.3584(19) yes
C3 . C4 . 1.491(17) yes
C3 . H31 . 0.934 no
C3 . C1 . 1.3584(19) yes
C3 . S10 . 1.6874(14) yes
C3 . H32 . 0.942 no
C1 . S41 . 1.540(8) yes
C1 . H11 . 0.932 no
C1 . C40 . 1.423(7) yes
C1 . H12 . 0.943 no
C4 . H41 . 0.925 no
C40 . H401 . 1.001 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
C6 . C2 . C4 . 127.3(6) yes
C6 . C2 . S41 . 125.4(3) yes
C4 . C2 . S41 . 107.3(7) yes
C6 . C2 . S10 . 117.04(9) yes
C6 . C2 . C40 . 132.6(3) yes
S10 . C2 . C40 . 110.4(3) yes
C2 . C6 . N7 . 112.29(10) yes
C2 . C6 . C11 . 126.71(11) yes
N7 . C6 . C11 . 121.00(11) yes
C6 . N7 . C8 . 116.99(10) yes
N7 . C8 . O9 . 128.36(11) yes
N7 . C8 . C19 . 121.01(11) yes
O9 . C8 . C19 . 110.57(10) yes
C8 . O9 . C10 . 118.28(9) yes
O9 . C10 . C11 . 115.92(10) yes
O9 . C10 . O18 . 115.96(11) yes
C11 . C10 . O18 . 128.11(11) yes
C10 . C11 . C6 . 119.45(11) yes
C10 . C11 . C12 . 115.02(10) yes
C6 . C11 . C12 . 125.52(11) yes
C11 . C12 . C13 . 121.15(11) yes
C11 . C12 . C17 . 119.39(10) yes
C13 . C12 . C17 . 119.42(11) yes
C12 . C13 . C14 . 119.75(12) yes
C12 . C13 . H131 . 119.2 no
C14 . C13 . H131 . 121.1 no
C13 . C14 . C15 . 120.53(12) yes
C13 . C14 . H141 . 120.0 no
C15 . C14 . H141 . 119.5 no
C14 . C15 . C16 . 119.83(12) yes
C14 . C15 . H151 . 120.3 no
C16 . C15 . H151 . 119.9 no
C15 . C16 . C17 . 120.11(13) yes
C15 . C16 . H161 . 120.1 no
C17 . C16 . H161 . 119.8 no
C12 . C17 . C16 . 120.36(12) yes
C12 . C17 . H171 . 118.8 no
C16 . C17 . H171 . 120.8 no
C8 . C19 . F20 . 110.36(11) yes
C8 . C19 . F21 . 111.75(11) yes
F20 . C19 . F21 . 108.21(11) yes
C8 . C19 . F22 . 111.54(10) yes
F20 . C19 . F22 . 106.89(11) yes
F21 . C19 . F22 . 107.90(11) yes
C1 . C3 . C4 . 100.3(5) yes
C1 . C3 . H31 . 131.5 no
C4 . C3 . H31 . 127.9 no
C1 . C3 . S10 . 114.09(10) yes
C1 . C3 . H32 . 124.0 no
S10 . C3 . H32 . 121.9 no
C3 . C1 . S41 . 123.8(3) yes
C3 . C1 . H11 . 117.8 no
S41 . C1 . H11 . 118.4 no
C3 . C1 . C40 . 110.6(2) yes
C3 . C1 . H12 . 124.9 no
C40 . C1 . H12 . 124.5 no
C2 . S10 . C3 . 91.56(6) yes
C3 . C4 . C2 . 115.6(9) yes
C3 . C4 . H41 . 120.4 no
C2 . C4 . H41 . 122.1 no
C1 . C40 . C2 . 113.4(4) yes
C1 . C40 . H401 . 122.6 no
C2 . C40 . H401 . 123.8 no
C2 . S41 . C1 . 93.0(4) yes



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
