# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_psu-505(bara-35)-2
_database_code_depnum_ccdc_archive 'CCDC 1905220'
loop_
_audit_author_name
_audit_author_address
'Maksim Dmitriev'
;Perm State University
Russia
;
_audit_update_record             
;
2019-03-24 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3877(14)
_cell_length_b                   9.9122(19)
_cell_length_c                   14.758(3)
_cell_angle_alpha                79.468(16)
_cell_angle_beta                 78.355(18)
_cell_angle_gamma                72.386(18)
_cell_volume                     864.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1331
_cell_measurement_theta_min      3.3800
_cell_measurement_theta_max      27.4530

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75471
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6426
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         29.26
_reflns_number_total             3957
_reflns_number_gt                2418
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0740P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3957
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.469(3) 0.3207(19) 0.5082(12) 0.050(5) Uiso 1 1 d . . .
O1 O -0.20937(19) 0.57591(14) 0.38167(8) 0.0561(4) Uani 1 1 d . . .
O2 O -0.16830(18) 0.58635(13) 0.22771(7) 0.0505(3) Uani 1 1 d . . .
C5 C 0.1432(2) 0.45853(16) 0.30048(10) 0.0348(4) Uani 1 1 d . . .
C13 C -0.0946(3) 0.54559(17) 0.30902(11) 0.0382(4) Uani 1 1 d . . .
C2 C 0.5831(3) 0.29863(17) 0.29306(10) 0.0389(4) Uani 1 1 d . . .
H2 H 0.7320 0.2471 0.2899 0.047 Uiso 1 1 calc R . .
C6 C 0.2361(3) 0.41468(17) 0.38097(10) 0.0387(4) Uani 1 1 d . . .
H6 H 0.1506 0.4404 0.4373 0.046 Uiso 1 1 calc R . .
N1 N 0.5409(3) 0.28190(17) 0.46160(10) 0.0521(4) Uani 1 1 d . . .
C4 C 0.2682(3) 0.42128(17) 0.21513(10) 0.0376(4) Uani 1 1 d . . .
H4 H 0.2044 0.4497 0.1609 0.045 Uiso 1 1 calc R . .
C1 C 0.4585(3) 0.33149(17) 0.37963(10) 0.0379(4) Uani 1 1 d . . .
C3 C 0.4898(3) 0.34105(17) 0.21185(10) 0.0370(4) Uani 1 1 d . . .
C7 C 0.6263(3) 0.29755(18) 0.12195(10) 0.0416(4) Uani 1 1 d . . .
C16 C 0.8051(3) 0.13656(17) 0.56350(10) 0.0392(4) Uani 1 1 d . . .
C15 C 0.7696(3) 0.2027(2) 0.46560(11) 0.0497(5) Uani 1 1 d . . .
H15A H 0.8637 0.2661 0.4423 0.060 Uiso 1 1 calc R . .
H15B H 0.8127 0.1281 0.4256 0.060 Uiso 1 1 calc R . .
C17 C 0.9505(3) 0.1703(2) 0.60652(12) 0.0526(5) Uani 1 1 d . . .
H17 H 1.0248 0.2370 0.5754 0.063 Uiso 1 1 calc R . .
C14 C -0.3984(3) 0.6702(2) 0.23028(14) 0.0603(5) Uani 1 1 d . . .
H14A H -0.4916 0.6229 0.2761 0.090 Uiso 1 1 calc R . .
H14B H -0.4411 0.6804 0.1701 0.090 Uiso 1 1 calc R . .
H14C H -0.4150 0.7629 0.2464 0.090 Uiso 1 1 calc R . .
C20 C 0.7349(4) -0.0274(2) 0.69989(13) 0.0611(5) Uani 1 1 d . . .
H20 H 0.6617 -0.0945 0.7313 0.073 Uiso 1 1 calc R . .
C19 C 0.8806(3) 0.0084(2) 0.74187(12) 0.0604(6) Uani 1 1 d . . .
H19 H 0.9058 -0.0342 0.8017 0.072 Uiso 1 1 calc R . .
C21 C 0.6972(3) 0.0361(2) 0.61128(12) 0.0522(5) Uani 1 1 d . . .
H21 H 0.5985 0.0113 0.5832 0.063 Uiso 1 1 calc R . .
C8 C 0.8272(3) 0.3287(2) 0.08949(12) 0.0608(5) Uani 1 1 d . . .
H8 H 0.8778 0.3783 0.1242 0.073 Uiso 1 1 calc R . .
C18 C 0.9883(4) 0.1070(2) 0.69508(13) 0.0645(6) Uani 1 1 d . . .
H18 H 1.0873 0.1313 0.7232 0.077 Uiso 1 1 calc R . .
C12 C 0.5563(3) 0.2228(2) 0.06963(12) 0.0612(5) Uani 1 1 d . . .
H12 H 0.4211 0.2013 0.0898 0.073 Uiso 1 1 calc R . .
C11 C 0.6858(4) 0.1794(3) -0.01291(13) 0.0785(7) Uani 1 1 d . . .
H11 H 0.6377 0.1281 -0.0474 0.094 Uiso 1 1 calc R . .
C10 C 0.8842(4) 0.2116(3) -0.04378(13) 0.0783(7) Uani 1 1 d . . .
H10 H 0.9711 0.1818 -0.0990 0.094 Uiso 1 1 calc R . .
C9 C 0.9542(4) 0.2876(3) 0.00652(14) 0.0782(7) Uani 1 1 d . . .
H9 H 1.0871 0.3117 -0.0150 0.094 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.2018(18) . ?
O2 C13 1.3266(18) . ?
O2 C14 1.450(2) . ?
C5 C6 1.376(2) . ?
C5 C4 1.395(2) . ?
C5 C13 1.496(2) . ?
C2 C3 1.386(2) . ?
C2 C1 1.399(2) . ?
C2 H2 0.9300 . ?
C6 C1 1.408(2) . ?
C6 H6 0.9300 . ?
N1 C1 1.366(2) . ?
N1 C15 1.441(2) . ?
N1 H1 0.832(18) . ?
C4 C3 1.394(2) . ?
C4 H4 0.9300 . ?
C3 C7 1.490(2) . ?
C7 C12 1.376(2) . ?
C7 C8 1.381(2) . ?
C16 C17 1.372(2) . ?
C16 C21 1.389(2) . ?
C16 C15 1.505(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.377(2) . ?
C17 H17 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C20 C19 1.374(3) . ?
C20 C21 1.378(2) . ?
C20 H20 0.9300 . ?
C19 C18 1.369(3) . ?
C19 H19 0.9300 . ?
C21 H21 0.9300 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C18 H18 0.9300 . ?
C12 C11 1.387(3) . ?
C12 H12 0.9300 . ?
C11 C10 1.369(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.364(3) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C14 116.44(13) . . ?
C6 C5 C4 120.44(15) . . ?
C6 C5 C13 117.32(13) . . ?
C4 C5 C13 122.24(14) . . ?
O1 C13 O2 122.81(15) . . ?
O1 C13 C5 124.06(15) . . ?
O2 C13 C5 113.13(13) . . ?
C3 C2 C1 121.55(15) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C5 C6 C1 121.21(14) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C1 N1 C15 122.87(14) . . ?
C1 N1 H1 116.9(12) . . ?
C15 N1 H1 117.2(12) . . ?
C3 C4 C5 119.36(14) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C1 C2 122.81(15) . . ?
N1 C1 C6 119.63(14) . . ?
C2 C1 C6 117.51(14) . . ?
C2 C3 C4 119.88(14) . . ?
C2 C3 C7 119.55(14) . . ?
C4 C3 C7 120.56(14) . . ?
C12 C7 C8 118.16(16) . . ?
C12 C7 C3 120.49(15) . . ?
C8 C7 C3 121.35(16) . . ?
C17 C16 C21 118.36(15) . . ?
C17 C16 C15 120.89(16) . . ?
C21 C16 C15 120.71(15) . . ?
N1 C15 C16 111.70(13) . . ?
N1 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N1 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C16 C17 C18 121.08(17) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C20 C21 120.13(18) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C18 C19 C20 119.63(17) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C20 C21 C16 120.59(17) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C9 C8 C7 121.32(19) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C19 C18 C17 120.22(18) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C7 C12 C11 120.53(18) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C9 C10 C11 119.88(19) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O2 C13 O1 -0.3(2) . . . . ?
C14 O2 C13 C5 179.45(13) . . . . ?
C6 C5 C13 O1 -2.0(2) . . . . ?
C4 C5 C13 O1 177.60(15) . . . . ?
C6 C5 C13 O2 178.24(13) . . . . ?
C4 C5 C13 O2 -2.2(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C13 C5 C6 C1 179.55(14) . . . . ?
C6 C5 C4 C3 -1.0(2) . . . . ?
C13 C5 C4 C3 179.40(14) . . . . ?
C15 N1 C1 C2 6.1(3) . . . . ?
C15 N1 C1 C6 -176.59(16) . . . . ?
C3 C2 C1 N1 174.83(15) . . . . ?
C3 C2 C1 C6 -2.6(2) . . . . ?
C5 C6 C1 N1 -175.68(15) . . . . ?
C5 C6 C1 C2 1.8(2) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C1 C2 C3 C7 -177.11(14) . . . . ?
C5 C4 C3 C2 0.3(2) . . . . ?
C5 C4 C3 C7 178.94(14) . . . . ?
C2 C3 C7 C12 123.25(19) . . . . ?
C4 C3 C7 C12 -55.4(2) . . . . ?
C2 C3 C7 C8 -55.7(2) . . . . ?
C4 C3 C7 C8 125.63(18) . . . . ?
C1 N1 C15 C16 -168.71(15) . . . . ?
C17 C16 C15 N1 -120.26(18) . . . . ?
C21 C16 C15 N1 62.0(2) . . . . ?
C21 C16 C17 C18 -0.3(3) . . . . ?
C15 C16 C17 C18 -178.13(17) . . . . ?
C21 C20 C19 C18 -0.2(3) . . . . ?
C19 C20 C21 C16 -0.1(3) . . . . ?
C17 C16 C21 C20 0.3(3) . . . . ?
C15 C16 C21 C20 178.12(17) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
C3 C7 C8 C9 179.60(19) . . . . ?
C20 C19 C18 C17 0.2(3) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C8 C7 C12 C11 0.5(3) . . . . ?
C3 C7 C12 C11 -178.47(18) . . . . ?
C7 C12 C11 C10 -0.6(3) . . . . ?
C12 C11 C10 C9 -0.4(4) . . . . ?
C11 C10 C9 C8 1.6(4) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.840
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_psu-831(r-44-r)
_database_code_depnum_ccdc_archive 'CCDC 1905221'
loop_
_audit_author_name
_audit_author_address
'Maksim Dmitriev'
;Perm State University
Russia
;
_audit_update_record             
;
2019-03-24 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 F3 O2 S'
_chemical_formula_sum            'C11 H9 F3 O2 S'
_chemical_formula_weight         262.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N1 O3 S1 F3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.470(2)
_cell_length_b                   13.267(3)
_cell_length_c                   9.675(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.53(2)
_cell_angle_gamma                90
_cell_volume                     1086.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1939
_cell_measurement_temperature    295
_cell_measurement_theta_max      28.7160
_cell_measurement_theta_min      3.7170
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6252
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.420
_diffrn_reflns_theta_min         3.509
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -95.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7103  -19.0000    0.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7103  -19.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7103  -99.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega  -82.00  -52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2416  -38.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega  -30.00    8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2416  -38.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega  -98.00  -64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2416  -19.0000  -30.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0779981000
_diffrn_orient_matrix_UB_12      0.0138010000
_diffrn_orient_matrix_UB_13      -0.0205835000
_diffrn_orient_matrix_UB_21      -0.0211953000
_diffrn_orient_matrix_UB_22      0.0024807000
_diffrn_orient_matrix_UB_23      0.0702983000
_diffrn_orient_matrix_UB_31      0.0222662000
_diffrn_orient_matrix_UB_32      0.0515954000
_diffrn_orient_matrix_UB_33      0.0019613000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2093
_reflns_number_total             2635
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2635
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.3586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1221
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5704(2) 0.19582(13) 0.44350(17) 0.0287(4) Uani 1 1 d . . . . .
C2 C 0.6571(2) 0.26390(14) 0.5146(2) 0.0371(4) Uani 1 1 d . . . . .
H2 H 0.764951 0.252563 0.526604 0.044 Uiso 1 1 calc R . . . .
C3 C 0.5906(2) 0.35371(14) 0.57304(19) 0.0363(4) Uani 1 1 d . . . . .
C4 C 0.4133(2) 0.36229(15) 0.5716(2) 0.0385(4) Uani 1 1 d . . . . .
H4A H 0.383814 0.432730 0.578220 0.046 Uiso 1 1 calc R . . . .
H4B H 0.372764 0.327475 0.651318 0.046 Uiso 1 1 calc R . . . .
C5 C 0.3399(2) 0.31771(13) 0.44113(18) 0.0303(4) Uani 1 1 d . . . . .
C6 C 0.3966(2) 0.21107(13) 0.41478(19) 0.0314(4) Uani 1 1 d . . . . .
H6A H 0.338190 0.165079 0.472209 0.038 Uiso 1 1 calc R . . . .
H6B H 0.372922 0.193859 0.319026 0.038 Uiso 1 1 calc R . . . .
C7 C 0.1606(2) 0.31812(14) 0.4516(2) 0.0390(4) Uani 1 1 d . . . . .
C8 C 0.6375(2) 0.10318(13) 0.39187(18) 0.0299(4) Uani 1 1 d . . . . .
C9 C 0.5697(2) 0.03428(13) 0.3014(2) 0.0360(4) Uani 1 1 d . . . . .
H9 H 0.467708 0.039774 0.264180 0.043 Uiso 1 1 calc R . . . .
C10 C 0.6743(3) -0.04588(14) 0.2718(2) 0.0419(5) Uani 1 1 d . . . . .
H10 H 0.648514 -0.098230 0.211415 0.050 Uiso 1 1 calc R . . . .
C11 C 0.8135(2) -0.03874(15) 0.3395(2) 0.0407(5) Uani 1 1 d . . . . .
H11 H 0.894500 -0.085593 0.332100 0.049 Uiso 1 1 calc R . . . .
F1 F 0.08851(15) 0.27481(10) 0.34366(15) 0.0589(4) Uani 1 1 d . . . . .
F2 F 0.10315(14) 0.41060(9) 0.46222(14) 0.0498(3) Uani 1 1 d . . . . .
F3 F 0.11145(15) 0.26785(10) 0.56357(15) 0.0592(4) Uani 1 1 d . . . . .
O1 O 0.37865(17) 0.37484(11) 0.32351(14) 0.0411(3) Uani 1 1 d . . . . .
H1 H 0.363(3) 0.436(2) 0.341(3) 0.064(8) Uiso 1 1 d . . . . .
O2 O 0.67366(18) 0.41830(10) 0.62791(17) 0.0504(4) Uani 1 1 d . . . . .
S1 S 0.82520(6) 0.06526(4) 0.43998(6) 0.04459(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.342(3) . ?
C1 C6 1.504(2) . ?
C1 C8 1.449(2) . ?
C2 C3 1.440(3) . ?
C3 C4 1.506(3) . ?
C3 O2 1.221(2) . ?
C4 C5 1.512(3) . ?
C5 C6 1.518(2) . ?
C5 C7 1.525(3) . ?
C5 O1 1.413(2) . ?
C7 F1 1.327(2) . ?
C7 F2 1.325(2) . ?
C7 F3 1.347(2) . ?
C8 C9 1.380(3) . ?
C8 S1 1.7199(18) . ?
C9 C10 1.418(3) . ?
C10 C11 1.337(3) . ?
C11 S1 1.689(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.57(16) . . ?
C2 C1 C8 122.23(17) . . ?
C8 C1 C6 116.20(15) . . ?
C1 C2 C3 122.95(17) . . ?
C2 C3 C4 117.33(16) . . ?
O2 C3 C2 121.67(18) . . ?
O2 C3 C4 120.91(18) . . ?
C3 C4 C5 111.47(16) . . ?
C4 C5 C6 112.31(15) . . ?
C4 C5 C7 109.33(16) . . ?
C6 C5 C7 109.56(15) . . ?
O1 C5 C4 111.30(15) . . ?
O1 C5 C6 106.46(14) . . ?
O1 C5 C7 107.75(15) . . ?
C1 C6 C5 114.01(14) . . ?
F1 C7 C5 112.59(16) . . ?
F1 C7 F3 105.84(16) . . ?
F2 C7 C5 112.14(16) . . ?
F2 C7 F1 107.45(16) . . ?
F2 C7 F3 105.92(16) . . ?
F3 C7 C5 112.42(16) . . ?
C1 C8 S1 121.55(13) . . ?
C9 C8 C1 128.35(16) . . ?
C9 C8 S1 110.09(14) . . ?
C8 C9 C10 111.93(17) . . ?
C11 C10 C9 113.31(18) . . ?
C10 C11 S1 112.16(15) . . ?
C11 S1 C8 92.50(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.84(3) 1.99(3) 2.821(2) 177(3) 3_666 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_psu-683(bara-67)
_database_code_depnum_ccdc_archive 'CCDC 1905223'
loop_
_audit_author_name
_audit_author_address
'Maksim Dmitriev'
;Perm State University
Russia
;
_audit_update_record             
;
2019-03-24 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 Cl F3 N'
_chemical_formula_sum            'C19 H13 Cl F3 N'
_chemical_formula_weight         347.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.452(7)
_cell_length_b                   16.461(7)
_cell_length_c                   10.122(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3241(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1785
_cell_measurement_theta_min      3.2520
_cell_measurement_theta_max      23.1150
_cell_measurement_temperature    295
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_min  0.85371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11089
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.468
_diffrn_reflns_theta_min         3.157
_diffrn_ambient_temperature      295.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2212
_reflns_number_total             3920
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+0.3880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1354
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(F1A)=Sof(F2A)=Sof(F23A)=1-FVAR(1)
 Sof(F1)=Sof(F3)=Sof(F3A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55730(11) 0.61608(12) 1.0350(2) 0.0552(5) Uani 1 1 d . . . . .
C2 C 0.60456(11) 0.55466(13) 1.0090(2) 0.0586(6) Uani 1 1 d . . . . .
H2 H 0.636542 0.539550 1.072689 0.070 Uiso 1 1 calc R . . . .
C3 C 0.60354(11) 0.51649(12) 0.8880(2) 0.0555(5) Uani 1 1 d . . . . .
C4 C 0.55806(11) 0.53828(12) 0.7905(2) 0.0566(6) Uani 1 1 d . . . . .
H4 H 0.558980 0.511905 0.709266 0.068 Uiso 1 1 calc R . . . .
C5 C 0.51047(11) 0.60007(12) 0.8136(2) 0.0529(5) Uani 1 1 d . . . . .
C6 C 0.51091(12) 0.63698(12) 0.9369(2) 0.0565(6) Uani 1 1 d . . . . .
H6 H 0.478750 0.677386 0.954343 0.068 Uiso 1 1 calc R . . . .
C7 C 0.46191(12) 0.62670(12) 0.7098(2) 0.0552(6) Uani 1 1 d . . . . .
C8 C 0.48066(13) 0.62857(13) 0.5773(2) 0.0671(6) Uani 1 1 d . . . . .
H8 H 0.525028 0.613586 0.553267 0.081 Uiso 1 1 calc R . . . .
C9 C 0.43498(17) 0.65210(16) 0.4814(3) 0.0792(8) Uani 1 1 d . . . . .
H9 H 0.448699 0.652777 0.393414 0.095 Uiso 1 1 calc R . . . .
C10 C 0.36919(18) 0.67465(15) 0.5141(3) 0.0833(8) Uani 1 1 d . . . . .
H10 H 0.338351 0.690553 0.448873 0.100 Uiso 1 1 calc R . . . .
C11 C 0.34951(14) 0.67343(16) 0.6441(3) 0.0826(8) Uani 1 1 d . . . . .
H11 H 0.304927 0.688285 0.666844 0.099 Uiso 1 1 calc R . . . .
C12 C 0.39500(14) 0.65047(14) 0.7415(3) 0.0681(6) Uani 1 1 d . . . . .
H12 H 0.380990 0.650793 0.829353 0.082 Uiso 1 1 calc R . . . .
C13 C 0.59786(11) 0.65055(13) 1.2642(2) 0.0547(5) Uani 1 1 d . . . . .
C14 C 0.62327(11) 0.71873(12) 1.3266(2) 0.0575(5) Uani 1 1 d . . . . .
H14 H 0.614299 0.769784 1.291184 0.069 Uiso 1 1 calc R . . . .
C15 C 0.66150(11) 0.71248(13) 1.4397(2) 0.0608(6) Uani 1 1 d . . . . .
H15 H 0.677461 0.759157 1.481427 0.073 Uiso 1 1 calc R . . . .
C16 C 0.67636(11) 0.63731(13) 1.4918(2) 0.0581(6) Uani 1 1 d . . . . .
C17 C 0.65151(12) 0.56864(13) 1.4308(2) 0.0628(6) Uani 1 1 d . . . . .
H17 H 0.661492 0.517626 1.465290 0.075 Uiso 1 1 calc R . . . .
C18 C 0.61200(12) 0.57535(12) 1.3189(2) 0.0615(6) Uani 1 1 d . . . . .
H18 H 0.594506 0.528734 1.279399 0.074 Uiso 1 1 calc R . . . .
C19 C 0.65304(14) 0.44860(16) 0.8627(3) 0.0692(7) Uani 1 1 d . . . . .
Cl1 Cl 0.72581(3) 0.62946(4) 1.63387(6) 0.0813(3) Uani 1 1 d . . . . .
N1 N 0.55578(12) 0.66015(14) 1.1526(2) 0.0690(6) Uani 1 1 d . . . . .
H1 H 0.5367(14) 0.7053(17) 1.145(2) 0.094(10) Uiso 1 1 d . . . . .
F1 F 0.6210(5) 0.3776(4) 0.8517(9) 0.102(3) Uani 0.593(19) 1 d . . P A 1
F3 F 0.6953(6) 0.4323(7) 0.9645(7) 0.105(2) Uani 0.593(19) 1 d . . P A 1
F3A F 0.6887(7) 0.4545(6) 0.7588(11) 0.127(4) Uani 0.593(19) 1 d . . P A 1
F1A F 0.6361(11) 0.3831(9) 0.912(3) 0.172(8) Uani 0.407(19) 1 d . . P A 2
F2A F 0.7156(5) 0.4705(12) 0.899(3) 0.127(6) Uani 0.407(19) 1 d . . P A 2
F23A F 0.6643(9) 0.4350(10) 0.7372(10) 0.123(5) Uani 0.407(19) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.392(3) . ?
C1 C6 1.386(3) . ?
C1 N1 1.394(3) . ?
C2 C3 1.377(3) . ?
C3 C4 1.373(3) . ?
C3 C19 1.497(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.388(3) . ?
C5 C7 1.479(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.397(3) . ?
C8 C9 1.372(3) . ?
C9 C10 1.373(4) . ?
C10 C11 1.370(4) . ?
C11 C12 1.377(3) . ?
C13 C14 1.379(3) . ?
C13 C18 1.384(3) . ?
C13 N1 1.404(3) . ?
C14 C15 1.369(3) . ?
C15 C16 1.376(3) . ?
C16 C17 1.376(3) . ?
C16 Cl1 1.734(2) . ?
C17 C18 1.373(3) . ?
C19 F1 1.329(8) . ?
C19 F3 1.346(5) . ?
C19 F3A 1.264(7) . ?
C19 F1A 1.233(12) . ?
C19 F2A 1.320(8) . ?
C19 F23A 1.308(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 123.6(2) . . ?
C6 C1 C2 118.34(19) . . ?
C6 C1 N1 118.0(2) . . ?
C3 C2 C1 119.4(2) . . ?
C2 C3 C19 118.9(2) . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 C19 119.12(19) . . ?
C3 C4 C5 119.85(19) . . ?
C4 C5 C7 121.39(19) . . ?
C6 C5 C4 117.7(2) . . ?
C6 C5 C7 120.9(2) . . ?
C1 C6 C5 122.7(2) . . ?
C8 C7 C5 121.6(2) . . ?
C8 C7 C12 117.4(2) . . ?
C12 C7 C5 121.0(2) . . ?
C9 C8 C7 121.3(3) . . ?
C8 C9 C10 120.6(3) . . ?
C11 C10 C9 119.2(3) . . ?
C10 C11 C12 120.8(3) . . ?
C11 C12 C7 120.7(2) . . ?
C14 C13 C18 118.3(2) . . ?
C14 C13 N1 119.0(2) . . ?
C18 C13 N1 122.6(2) . . ?
C15 C14 C13 121.1(2) . . ?
C14 C15 C16 120.2(2) . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 Cl1 120.09(18) . . ?
C17 C16 Cl1 120.40(18) . . ?
C18 C17 C16 120.1(2) . . ?
C17 C18 C13 120.9(2) . . ?
F1 C19 C3 111.7(5) . . ?
F1 C19 F3 100.1(6) . . ?
F3 C19 C3 114.3(3) . . ?
F3A C19 C3 116.0(4) . . ?
F3A C19 F1 104.8(6) . . ?
F3A C19 F3 108.5(5) . . ?
F1A C19 C3 114.4(6) . . ?
F1A C19 F2A 111.9(8) . . ?
F1A C19 F23A 106.7(11) . . ?
F2A C19 C3 110.0(4) . . ?
F23A C19 C3 113.7(6) . . ?
F23A C19 F2A 99.2(8) . . ?
C1 N1 C13 128.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_psu-345(md-356)
_database_code_depnum_ccdc_archive 'CCDC 1905222'
loop_
_audit_author_name
_audit_author_address
'Maksim Dmitriev'
;Perm State University
Russia
;
_audit_update_record             
;
2019-03-24 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2016-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H17 N O3'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6883(17)
_cell_length_b                   9.4591(15)
_cell_length_c                   11.7328(19)
_cell_angle_alpha                82.664(14)
_cell_angle_beta                 79.063(17)
_cell_angle_gamma                76.170(16)
_cell_volume                     810.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1861
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.8870
_cell_measurement_theta_min      4.0570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6254
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.439
_diffrn_reflns_theta_min         2.964
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   94.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -       14.0072   77.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   86.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -       14.0072   77.0000   90.0000 108

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   57.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541   77.0000 -180.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0563322000
_diffrn_orient_matrix_UB_12      -0.0152984000
_diffrn_orient_matrix_UB_13      -0.0542870000
_diffrn_orient_matrix_UB_21      -0.0003181000
_diffrn_orient_matrix_UB_22      0.0753626000
_diffrn_orient_matrix_UB_23      -0.0130852000
_diffrn_orient_matrix_UB_31      0.0781495000
_diffrn_orient_matrix_UB_32      -0.0097441000
_diffrn_orient_matrix_UB_33      0.0264836000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2429
_reflns_number_total             3760
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0892P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1868
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23659(17) 0.74534(12) 0.52581(11) 0.0556(4) Uani 1 1 d . . . . .
O2 O 0.37580(15) 0.59715(11) 0.38714(10) 0.0507(3) Uani 1 1 d . . . . .
O3 O 0.01390(19) 0.09953(15) 0.30686(14) 0.0649(4) Uani 1 1 d . . . . .
H3 H -0.047(3) 0.146(3) 0.365(2) 0.087(8) Uiso 1 1 d . . . . .
N1 N 0.1821(2) 0.13314(15) 0.48903(13) 0.0504(4) Uani 1 1 d . . . . .
H1 H 0.130(3) 0.075(2) 0.5293(17) 0.069(6) Uiso 1 1 d . . . . .
C1 C 0.0478(2) 0.38583(18) 0.71927(14) 0.0443(4) Uani 1 1 d . . . . .
C2 C 0.0752(2) 0.26335(17) 0.65975(14) 0.0451(4) Uani 1 1 d . . . . .
H2 H 0.0301 0.1835 0.6970 0.054 Uiso 1 1 calc R . . . .
C3 C 0.1677(2) 0.25541(16) 0.54628(13) 0.0418(4) Uani 1 1 d . . . . .
C4 C 0.2340(2) 0.37458(16) 0.49175(14) 0.0429(4) Uani 1 1 d . . . . .
H4 H 0.2970 0.3717 0.4158 0.052 Uiso 1 1 calc R . . . .
C5 C 0.2068(2) 0.49790(16) 0.54997(13) 0.0418(4) Uani 1 1 d . . . . .
C6 C 0.1152(2) 0.50509(17) 0.66271(14) 0.0449(4) Uani 1 1 d . . . . .
H6 H 0.0986 0.5889 0.7008 0.054 Uiso 1 1 calc R . . . .
C7 C -0.0548(2) 0.39042(19) 0.83951(15) 0.0505(4) Uani 1 1 d . . . . .
C8 C -0.0332(3) 0.2671(2) 0.91740(17) 0.0678(6) Uani 1 1 d . . . . .
H8 H 0.0470 0.1813 0.8944 0.081 Uiso 1 1 calc R . . . .
C9 C -0.1302(3) 0.2713(3) 1.02898(19) 0.0852(7) Uani 1 1 d . . . . .
H9 H -0.1136 0.1886 1.0813 0.102 Uiso 1 1 calc R . . . .
C10 C -0.2502(3) 0.3954(3) 1.06332(19) 0.0875(8) Uani 1 1 d . . . . .
H10 H -0.3170 0.3968 1.1382 0.105 Uiso 1 1 calc R . . . .
C11 C -0.2720(3) 0.5172(3) 0.9878(2) 0.0819(7) Uani 1 1 d . . . . .
H11 H -0.3530 0.6024 1.0113 0.098 Uiso 1 1 calc R . . . .
C12 C -0.1750(3) 0.5148(2) 0.87728(17) 0.0676(6) Uani 1 1 d . . . . .
H12 H -0.1907 0.5991 0.8265 0.081 Uiso 1 1 calc R . . . .
C13 C 0.2726(2) 0.62613(17) 0.48887(14) 0.0424(4) Uani 1 1 d . . . . .
C14 C 0.4322(3) 0.71634(19) 0.31353(16) 0.0589(5) Uani 1 1 d . . . . .
H14A H 0.5283 0.6789 0.2525 0.088 Uiso 1 1 calc GR . . . .
H14B H 0.4750 0.7747 0.3587 0.088 Uiso 1 1 calc GR . . . .
H14C H 0.3313 0.7753 0.2799 0.088 Uiso 1 1 calc GR . . . .
C15 C 0.2842(2) 0.10956(15) 0.37754(14) 0.0448(4) Uani 1 1 d . . . . .
C16 C 0.1957(2) 0.09391(16) 0.28831(15) 0.0493(4) Uani 1 1 d . . . . .
C17 C 0.2941(3) 0.0681(2) 0.17987(17) 0.0642(5) Uani 1 1 d . . . . .
H17 H 0.2362 0.0559 0.1202 0.077 Uiso 1 1 calc R . . . .
C18 C 0.4788(3) 0.0603(2) 0.15866(18) 0.0709(6) Uani 1 1 d . . . . .
H18 H 0.5445 0.0432 0.0847 0.085 Uiso 1 1 calc R . . . .
C19 C 0.5663(3) 0.0776(2) 0.24600(18) 0.0659(5) Uani 1 1 d . . . . .
H19 H 0.6906 0.0730 0.2314 0.079 Uiso 1 1 calc R . . . .
C20 C 0.4687(3) 0.10150(19) 0.35476(16) 0.0549(5) Uani 1 1 d . . . . .
H20 H 0.5277 0.1125 0.4142 0.066 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.2109(19) . ?
O2 C13 1.3226(19) . ?
O2 C14 1.4312(19) . ?
O3 H3 0.86(2) . ?
O3 C16 1.362(2) . ?
N1 H1 0.81(2) . ?
N1 C3 1.382(2) . ?
N1 C15 1.407(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.393(2) . ?
C1 C7 1.480(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C3 C4 1.381(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(2) . ?
C5 C6 1.377(2) . ?
C5 C13 1.475(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(3) . ?
C7 C12 1.376(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.357(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(3) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.393(2) . ?
C15 C20 1.377(2) . ?
C16 C17 1.370(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.368(3) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C14 117.76(13) . . ?
C16 O3 H3 115.0(16) . . ?
C3 N1 H1 111.5(14) . . ?
C3 N1 C15 123.95(13) . . ?
C15 N1 H1 124.5(14) . . ?
C2 C1 C6 118.53(15) . . ?
C2 C1 C7 120.32(15) . . ?
C6 C1 C7 121.14(15) . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.23(14) . . ?
C3 C2 H2 118.9 . . ?
N1 C3 C2 119.56(14) . . ?
C4 C3 N1 121.92(14) . . ?
C4 C3 C2 118.42(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.95(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C13 119.19(14) . . ?
C6 C5 C4 121.40(14) . . ?
C6 C5 C13 119.39(15) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.48(15) . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C1 120.24(17) . . ?
C12 C7 C1 121.86(16) . . ?
C12 C7 C8 117.90(17) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.5(2) . . ?
C11 C12 H12 119.3 . . ?
O1 C13 O2 123.04(14) . . ?
O1 C13 C5 124.68(15) . . ?
O2 C13 C5 112.28(13) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N1 118.82(16) . . ?
C20 C15 N1 121.71(15) . . ?
C20 C15 C16 119.48(16) . . ?
O3 C16 C15 121.63(16) . . ?
O3 C16 C17 118.96(16) . . ?
C17 C16 C15 119.38(17) . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.34(18) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.48(18) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.29(19) . . ?
C20 C19 H19 120.4 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 121.02(18) . . ?
C19 C20 H20 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.86(2) 1.93(3) 2.769(2) 165(2) 2_566

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C16 C17 C18 -179.32(16) . . . . ?
N1 C3 C4 C5 175.99(14) . . . . ?
N1 C15 C16 O3 -0.6(2) . . . . ?
N1 C15 C16 C17 -178.78(14) . . . . ?
N1 C15 C20 C19 179.58(15) . . . . ?
C1 C2 C3 N1 -176.44(15) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C7 C8 C9 -179.37(18) . . . . ?
C1 C7 C12 C11 178.66(18) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C2 C1 C7 C8 38.7(2) . . . . ?
C2 C1 C7 C12 -140.53(19) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 N1 C15 C16 -119.89(17) . . . . ?
C3 N1 C15 C20 60.2(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C5 C13 -177.74(14) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C13 O1 170.26(15) . . . . ?
C4 C5 C13 O2 -9.2(2) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C6 C1 C7 C8 -142.73(18) . . . . ?
C6 C1 C7 C12 38.0(3) . . . . ?
C6 C5 C13 O1 -8.0(3) . . . . ?
C6 C5 C13 O2 172.52(13) . . . . ?
C7 C1 C2 C3 178.83(15) . . . . ?
C7 C1 C6 C5 -178.65(14) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C8 C7 C12 C11 -0.6(3) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C7 0.3(4) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
C13 C5 C6 C1 177.94(14) . . . . ?
C14 O2 C13 O1 -6.1(2) . . . . ?
C14 O2 C13 C5 173.38(14) . . . . ?
C15 N1 C3 C2 -175.03(15) . . . . ?
C15 N1 C3 C4 8.7(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C15 C20 C19 -0.4(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -0.5(3) . . . . ?
C20 C15 C16 O3 179.31(14) . . . . ?
C20 C15 C16 C17 1.2(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_psu-1012(b-344)
_database_code_depnum_ccdc_archive 'CCDC 1960904'
loop_
_audit_author_name
_audit_author_address
'Maksim Dmitriev'
;Perm State University
Russia
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H16 F3 N O S'
_chemical_formula_sum            'C16 H16 F3 N O S'
_chemical_formula_weight         327.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.153(4)
_cell_length_b                   15.177(5)
_cell_length_c                   7.937(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.57(3)
_cell_angle_gamma                90
_cell_volume                     1518.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2321
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.7880
_cell_measurement_theta_min      3.6700
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7255
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.423
_diffrn_reflns_theta_min         3.232
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -27.00   38.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       14.1634  -38.0000 -120.0000 65

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00    3.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       14.1634   77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega   22.00   97.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       14.1634   77.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   26.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7103  -99.0000   60.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0070603000
_diffrn_orient_matrix_UB_12      -0.0389217000
_diffrn_orient_matrix_UB_13      0.0518727000
_diffrn_orient_matrix_UB_21      -0.0076974000
_diffrn_orient_matrix_UB_22      -0.0258331000
_diffrn_orient_matrix_UB_23      -0.0767036000
_diffrn_orient_matrix_UB_31      0.0553520000
_diffrn_orient_matrix_UB_32      0.0012360000
_diffrn_orient_matrix_UB_33      0.0096203000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2418
_reflns_number_total             3526
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.135(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.1001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1271
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1-C8 \\sim S1A-C8
 with sigma of 0.02
 S1-C11 \\sim S1A-C11A
 with sigma of 0.02
 C8-C9 \\sim C8-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 S1-C10 \\sim S1A-C10A
 with sigma of 0.04
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
 C8-C11 \\sim C8-C11A
 with sigma of 0.04
 C9-C11 \\sim C9A-C11A
 with sigma of 0.04
 F1-C12 \\sim F1A-C12
 with sigma of 0.02
 F2-C12 \\sim F2A-C12
 with sigma of 0.02
 F3-C12 \\sim F3A-C12
 with sigma of 0.02
3. Rigid bond restraints
 F1, F1A, F2, F2A, F3, F3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F1 \\sim F1A \\sim F2 \\sim F2A \\sim F3 \\sim F3A: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Others
 Sof(S1A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=1-FVAR(1)
 Sof(S1)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C9(H9), C9A(H9A), C10(H10), C10A(H10A), C11(H11), C11A(H11A)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.27116(12) 0.52167(11) 0.23355(19) 0.0361(4) Uani 1 1 d . . . . .
N1 N 0.22145(10) 0.59139(9) 0.12043(16) 0.0388(4) Uani 1 1 d . . . . .
O1 O 0.12309(11) 0.69376(10) -0.18088(15) 0.0618(4) Uani 1 1 d . . . . .
F1 F 0.5785(4) 0.4288(4) 0.2818(10) 0.092(2) Uani 0.593(15) 1 d D U P A 1
S1 S 0.31177(13) 0.36761(9) 0.81400(15) 0.0620(4) Uani 0.741(4) 1 d D . P B 1
F1A F 0.5807(7) 0.3610(9) 0.4504(12) 0.109(4) Uani 0.407(15) 1 d D U P A 2
S1A S 0.1049(7) 0.3627(6) 0.5842(11) 0.0467(11) Uani 0.259(4) 1 d D . P B 2
C2 C 0.36440(12) 0.48342(12) 0.2187(2) 0.0417(4) Uani 1 1 d . . . . .
H2 H 0.395177 0.503537 0.133981 0.050 Uiso 1 1 calc R . . . .
F2 F 0.5608(7) 0.3277(8) 0.4481(9) 0.132(3) Uani 0.593(15) 1 d D U P A 1
F2A F 0.4975(12) 0.2963(10) 0.239(3) 0.129(6) Uani 0.407(15) 1 d D U P A 2
C3 C 0.41125(12) 0.41553(12) 0.3300(2) 0.0427(4) Uani 1 1 d . . . . .
F3 F 0.4892(8) 0.3183(7) 0.1795(11) 0.100(3) Uani 0.593(15) 1 d D U P A 1
F3A F 0.5510(13) 0.4186(10) 0.204(3) 0.166(5) Uani 0.407(15) 1 d D U P A 2
C4 C 0.36566(13) 0.38430(12) 0.4536(2) 0.0436(4) Uani 1 1 d . . . . .
H4 H 0.396295 0.337037 0.524620 0.052 Uiso 1 1 calc R . . . .
C5 C 0.27363(13) 0.42309(11) 0.47340(19) 0.0379(4) Uani 1 1 d . . . . .
C6 C 0.22689(12) 0.49403(11) 0.36717(19) 0.0358(4) Uani 1 1 d . . . . .
C7 C 0.13751(14) 0.54500(12) 0.4045(2) 0.0478(4) Uani 1 1 d . . . . .
H7A H 0.071572 0.515393 0.351997 0.072 Uiso 1 1 calc GR . . . .
H7B H 0.135020 0.603199 0.356172 0.072 Uiso 1 1 calc GR . . . .
H7C H 0.148937 0.548888 0.529291 0.072 Uiso 1 1 calc GR . . . .
C8 C 0.23025(15) 0.38877(12) 0.6131(2) 0.0410(4) Uani 1 1 d D . . . .
C9 C 0.1296(7) 0.3636(8) 0.6060(15) 0.059(3) Uani 0.741(4) 1 d D . P B 1
H9 H 0.073307 0.367113 0.503990 0.071 Uiso 0.741(4) 1 calc R . P B 1
C9A C 0.2867(16) 0.3631(17) 0.777(3) 0.165(17) Uani 0.259(4) 1 d D . P B 2
H9A H 0.358859 0.374626 0.821492 0.198 Uiso 0.259(4) 1 calc R . P B 2
C10 C 0.1182(7) 0.3315(6) 0.7674(12) 0.054(2) Uani 0.741(4) 1 d D . P B 1
H10 H 0.054312 0.313641 0.784824 0.065 Uiso 0.741(4) 1 calc R . P B 1
C10A C 0.2290(19) 0.318(2) 0.877(3) 0.058(7) Uani 0.259(4) 1 d D . P B 2
H10A H 0.256962 0.295586 0.990025 0.070 Uiso 0.259(4) 1 calc R . P B 2
C11 C 0.2112(7) 0.3304(8) 0.8903(13) 0.060(2) Uani 0.741(4) 1 d D . P B 1
H11 H 0.220214 0.311385 1.005092 0.072 Uiso 0.741(4) 1 calc R . P B 1
C11A C 0.1287(18) 0.3124(16) 0.782(3) 0.044(4) Uani 0.259(4) 1 d D . P B 2
H11A H 0.076605 0.283796 0.819322 0.052 Uiso 0.259(4) 1 calc R . P B 2
C12 C 0.50938(15) 0.37347(15) 0.3091(3) 0.0550(5) Uani 1 1 d D . . . .
C13 C 0.11749(14) 0.56873(13) 0.0041(2) 0.0500(5) Uani 1 1 d . . . . .
H13A H 0.075000 0.540867 0.070836 0.060 Uiso 1 1 calc R . . . .
H13B H 0.125234 0.527554 -0.084931 0.060 Uiso 1 1 calc R . . . .
C14 C 0.06352(15) 0.65097(15) -0.0818(2) 0.0581(5) Uani 1 1 d . . . . .
H14A H -0.006011 0.636058 -0.158557 0.070 Uiso 1 1 calc R . . . .
H14B H 0.053799 0.690874 0.007781 0.070 Uiso 1 1 calc R . . . .
C15 C 0.22463(16) 0.71564(14) -0.0680(2) 0.0606(6) Uani 1 1 d . . . . .
H15A H 0.216487 0.756327 0.021553 0.073 Uiso 1 1 calc R . . . .
H15B H 0.265758 0.744868 -0.135393 0.073 Uiso 1 1 calc R . . . .
C16 C 0.28327(14) 0.63510(14) 0.0189(2) 0.0516(5) Uani 1 1 d . . . . .
H16A H 0.294394 0.595172 -0.069607 0.062 Uiso 1 1 calc R . . . .
H16B H 0.352057 0.651893 0.095772 0.062 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.421(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.411(2) . ?
N1 C13 1.456(2) . ?
N1 C16 1.457(2) . ?
O1 C14 1.416(2) . ?
O1 C15 1.419(2) . ?
F1 C12 1.300(5) . ?
S1 C8 1.680(2) . ?
S1 C11 1.701(9) . ?
F1A C12 1.254(8) . ?
S1A C8 1.646(8) . ?
S1A C11A 1.690(18) . ?
C2 C3 1.382(2) . ?
F2 C12 1.316(6) . ?
F2A C12 1.286(12) . ?
C3 C4 1.372(2) . ?
C3 C12 1.491(2) . ?
F3 C12 1.294(8) . ?
F3A C12 1.317(10) . ?
C4 C5 1.395(2) . ?
C5 C6 1.397(2) . ?
C5 C8 1.479(2) . ?
C6 C7 1.506(2) . ?
C8 C9 1.363(9) . ?
C8 C9A 1.359(17) . ?
C9 C10 1.418(12) . ?
C9A C10A 1.42(2) . ?
C10 C11 1.330(7) . ?
C10A C11A 1.323(15) . ?
C13 C14 1.500(3) . ?
C15 C16 1.504(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 121.00(14) . . ?
C2 C1 C6 120.12(14) . . ?
C6 C1 N1 118.83(14) . . ?
C1 N1 C13 113.87(13) . . ?
C1 N1 C16 117.36(13) . . ?
C13 N1 C16 109.14(13) . . ?
C14 O1 C15 109.07(13) . . ?
C8 S1 C11 92.9(3) . . ?
C8 S1A C11A 93.8(9) . . ?
C3 C2 C1 120.00(15) . . ?
C2 C3 C12 119.38(16) . . ?
C4 C3 C2 120.54(15) . . ?
C4 C3 C12 120.02(16) . . ?
C3 C4 C5 120.33(16) . . ?
C4 C5 C6 120.26(15) . . ?
C4 C5 C8 117.94(15) . . ?
C6 C5 C8 121.77(15) . . ?
C1 C6 C7 120.53(14) . . ?
C5 C6 C1 118.54(14) . . ?
C5 C6 C7 120.71(14) . . ?
C5 C8 S1 120.06(14) . . ?
C5 C8 S1A 124.4(3) . . ?
C9 C8 S1 109.6(5) . . ?
C9 C8 C5 130.2(5) . . ?
C9A C8 S1A 108.4(9) . . ?
C9A C8 C5 126.7(9) . . ?
C8 C9 C10 114.3(8) . . ?
C8 C9A C10A 116.1(16) . . ?
C11 C10 C9 110.8(8) . . ?
C11A C10A C9A 108(2) . . ?
C10 C11 S1 112.3(7) . . ?
C10A C11A S1A 113.2(19) . . ?
F1 C12 F2 105.3(5) . . ?
F1 C12 C3 114.2(3) . . ?
F1A C12 F2A 102.5(8) . . ?
F1A C12 C3 114.6(5) . . ?
F1A C12 F3A 107.9(8) . . ?
F2 C12 C3 112.8(3) . . ?
F2A C12 C3 115.8(7) . . ?
F2A C12 F3A 102.8(9) . . ?
F3 C12 F1 106.3(6) . . ?
F3 C12 F2 105.4(5) . . ?
F3 C12 C3 112.2(5) . . ?
F3A C12 C3 112.2(5) . . ?
N1 C13 C14 109.19(15) . . ?
O1 C14 C13 111.65(16) . . ?
O1 C15 C16 111.50(17) . . ?
N1 C16 C15 109.23(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
