# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_201709186
_database_code_depnum_ccdc_archive 'CCDC 1950379'
_audit_update_record             
;
2019-08-30 deposited with the CCDC.	2020-03-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 F3 N O3'
_chemical_formula_sum            'C19 H12 F3 N O3'
_chemical_formula_weight         359.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         C38H41N2O2F3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.8958(2)
_cell_length_b                   15.5043(9)
_cell_length_c                   17.1980(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.277(4)
_cell_angle_gamma                90
_cell_volume                     1551.49(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1349
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3950
_cell_measurement_theta_min      3.8560
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    1.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5737
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.056
_diffrn_reflns_theta_max         67.056
_diffrn_reflns_theta_min         3.862
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -76.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
  3 omega -102.00  -77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   55.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -116.0000  -15.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega   14.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega   75.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega   20.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  8 omega   56.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega   74.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 10 omega   -4.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
 14 omega   92.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega   55.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
 17 omega   61.00  131.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 18 omega   59.00  124.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  150.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0742962000
_diffrn_orient_matrix_UB_12      0.0474152000
_diffrn_orient_matrix_UB_13      0.0787020000
_diffrn_orient_matrix_UB_21      0.0313810000
_diffrn_orient_matrix_UB_22      -0.0872978000
_diffrn_orient_matrix_UB_23      0.0431840000
_diffrn_orient_matrix_UB_31      0.2521809000
_diffrn_orient_matrix_UB_32      -0.0031237000
_diffrn_orient_matrix_UB_33      -0.0132097000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1915
_reflns_number_total             2762
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.208
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0052(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.002
_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)+(0.0645P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1504
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), N1(H1)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_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 0.2663(4) 0.30773(17) 0.40498(14) 0.0480(6) Uani 1 1 d . . . . .
C2 C 0.1822(5) 0.39810(19) 0.42195(15) 0.0576(7) Uani 1 1 d . . . . .
C3 C -0.0675(4) 0.29620(19) 0.28706(14) 0.0551(7) Uani 1 1 d . . . . .
H3 H -0.1632 0.3383 0.3026 0.066 Uiso 1 1 calc R . . . .
C4 C 0.1431(4) 0.27368(18) 0.32728(13) 0.0476(6) Uani 1 1 d . . . . .
C5 C 0.2290(4) 0.20600(17) 0.28342(13) 0.0478(6) Uani 1 1 d . . . . .
C6 C 0.0621(4) 0.19169(18) 0.21649(14) 0.0526(6) Uani 1 1 d . . . . .
C7 C 0.0879(5) 0.1300(2) 0.15994(14) 0.0633(8) Uani 1 1 d . . . . .
H7 H -0.0249 0.1214 0.1162 0.076 Uiso 1 1 calc R . . . .
C8 C 0.2851(5) 0.0825(2) 0.17115(17) 0.0694(8) Uani 1 1 d . . . . .
H8 H 0.3064 0.0406 0.1343 0.083 Uiso 1 1 calc R . . . .
C9 C 0.4564(5) 0.0952(2) 0.23665(16) 0.0665(8) Uani 1 1 d . . . . .
H9 H 0.5893 0.0619 0.2424 0.080 Uiso 1 1 calc R . . . .
C10 C 0.4304(4) 0.15630(19) 0.29258(15) 0.0570(7) Uani 1 1 d . . . . .
H10 H 0.5449 0.1645 0.3359 0.068 Uiso 1 1 calc R . . . .
C11 C 0.4128(4) 0.24385(19) 0.54326(14) 0.0520(6) Uani 1 1 d . . . . .
C12 C 0.2350(4) 0.24653(17) 0.47302(13) 0.0461(6) Uani 1 1 d . . . . .
C13 C 0.0498(4) 0.19573(18) 0.46989(14) 0.0510(6) Uani 1 1 d . . . . .
H13 H -0.0631 0.1977 0.4254 0.061 Uiso 1 1 calc R . . . .
C14 C 0.0200(4) 0.13833(18) 0.53304(14) 0.0524(6) Uani 1 1 d . . . . .
C15 C 0.1900(5) 0.13651(18) 0.59831(14) 0.0554(6) Uani 1 1 d . . . . .
C16 C 0.1777(6) 0.0823(2) 0.66165(16) 0.0709(8) Uani 1 1 d . . . . .
H16 H 0.2949 0.0816 0.7049 0.085 Uiso 1 1 calc R . . . .
C17 C -0.0102(6) 0.0298(2) 0.65930(18) 0.0781(9) Uani 1 1 d . . . . .
H17 H -0.0207 -0.0066 0.7015 0.094 Uiso 1 1 calc R . . . .
C18 C -0.1848(6) 0.0303(2) 0.5949(2) 0.0769(9) Uani 1 1 d . . . . .
H18 H -0.3115 -0.0057 0.5941 0.092 Uiso 1 1 calc R . . . .
C19 C -0.1703(5) 0.0842(2) 0.53206(17) 0.0678(8) Uani 1 1 d . . . . .
H19 H -0.2876 0.0845 0.4888 0.081 Uiso 1 1 calc R . . . .
F1 F 0.1961(3) 0.45280(12) 0.36309(10) 0.0804(6) Uani 1 1 d . . . . .
F2 F -0.0368(3) 0.39840(12) 0.43408(10) 0.0737(5) Uani 1 1 d . . . . .
F3 F 0.3068(3) 0.43228(12) 0.48634(10) 0.0764(5) Uani 1 1 d . . . . .
N1 N -0.1157(3) 0.24735(17) 0.22067(12) 0.0589(6) Uani 1 1 d . . . . .
H1 H -0.2392 0.2509 0.1865 0.071 Uiso 1 1 calc R . . . .
O1 O 0.5026(3) 0.31656(15) 0.39718(10) 0.0617(6) Uani 1 1 d . . . . .
H1A H 0.5805 0.3217 0.4410 0.093 Uiso 1 1 calc GR . . . .
O2 O 0.5890(3) 0.28516(14) 0.55392(11) 0.0656(6) Uani 1 1 d . . . . .
O3 O 0.3812(3) 0.18831(13) 0.60231(10) 0.0589(5) 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 1.530(4) . ?
C1 C4 1.510(3) . ?
C1 C12 1.541(3) . ?
C1 O1 1.428(3) . ?
C2 F1 1.333(3) . ?
C2 F2 1.340(3) . ?
C2 F3 1.336(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(3) . ?
C3 N1 1.361(3) . ?
C4 C5 1.432(4) . ?
C5 C6 1.406(3) . ?
C5 C10 1.403(4) . ?
C6 C7 1.390(4) . ?
C6 N1 1.369(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.400(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.467(3) . ?
C11 O2 1.209(3) . ?
C11 O3 1.367(3) . ?
C12 C13 1.341(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.437(3) . ?
C14 C15 1.379(3) . ?
C14 C19 1.399(4) . ?
C15 C16 1.387(4) . ?
C15 O3 1.377(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(4) . ?
C19 H19 0.9300 . ?
N1 H1 0.8600 . ?
O1 H1A 0.8200 . ?

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 C12 109.7(2) . . ?
C4 C1 C2 111.4(2) . . ?
C4 C1 C12 111.0(2) . . ?
O1 C1 C2 106.3(2) . . ?
O1 C1 C4 106.73(19) . . ?
O1 C1 C12 111.62(19) . . ?
F1 C2 C1 112.1(2) . . ?
F1 C2 F2 107.1(2) . . ?
F1 C2 F3 106.5(2) . . ?
F2 C2 C1 112.5(2) . . ?
F3 C2 C1 111.7(2) . . ?
F3 C2 F2 106.5(2) . . ?
C4 C3 H3 125.3 . . ?
N1 C3 H3 125.3 . . ?
N1 C3 C4 109.4(2) . . ?
C3 C4 C1 128.8(2) . . ?
C3 C4 C5 106.9(2) . . ?
C5 C4 C1 124.2(2) . . ?
C6 C5 C4 106.7(2) . . ?
C10 C5 C4 135.1(2) . . ?
C10 C5 C6 118.2(2) . . ?
C7 C6 C5 122.7(3) . . ?
N1 C6 C5 107.4(2) . . ?
N1 C6 C7 129.9(2) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.4(2) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 H8 119.1 . . ?
C7 C8 C9 121.8(3) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 120.4 . . ?
C9 C10 C5 119.2(2) . . ?
C9 C10 H10 120.4 . . ?
O2 C11 C12 126.3(3) . . ?
O2 C11 O3 115.9(2) . . ?
O3 C11 C12 117.7(2) . . ?
C11 C12 C1 119.1(2) . . ?
C13 C12 C1 121.9(2) . . ?
C13 C12 C11 119.1(2) . . ?
C12 C13 H13 118.9 . . ?
C12 C13 C14 122.1(2) . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 C19 118.3(3) . . ?
C19 C14 C13 123.9(2) . . ?
C14 C15 C16 121.9(3) . . ?
O3 C15 C14 120.7(2) . . ?
O3 C15 C16 117.4(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 120.9(3) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C3 N1 C6 109.7(2) . . ?
C3 N1 H1 125.2 . . ?
C6 N1 H1 125.2 . . ?
C1 O1 H1A 109.5 . . ?
C11 O3 C15 122.59(19) . . ?

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
N1 H1 O2 0.86 2.41 3.146(3) 144.3 4_465
N1 H1 O3 0.86 2.64 3.462(3) 161.5 4_465
O1 H1A O2 0.82 2.02 2.705(3) 141.3 .

_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_20180138
_database_code_depnum_ccdc_archive 'CCDC 1950380'
_audit_update_record             
;
2019-08-30 deposited with the CCDC.	2020-03-22 downloaded from the CCDC.
;
_audit_creation_date             2018-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 F3 N O5'
_chemical_formula_sum            'C34 H26 F3 N O5'
_chemical_formula_weight         585.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H30O5F2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.1710(10)
_cell_length_b                   8.6836(3)
_cell_length_c                   32.4701(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.054(5)
_cell_angle_gamma                90
_cell_volume                     5833.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5050
_cell_measurement_theta_min      4.1900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            13560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.221
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -41.00  -12.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
  2 omega   61.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega   31.00   77.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega    5.00   50.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -42.0000 -168.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   61.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega  -31.00   59.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000    0.0000 180

#__ type_ start__ end____ width___ exp.time_
  7 omega  -26.00    6.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   90.0000 64

#__ type_ start__ end____ width___ exp.time_
  8 omega   10.00   36.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  9 omega   19.00   45.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega    8.00   65.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 114

#__ type_ start__ end____ width___ exp.time_
 11 omega   77.00  102.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00   83.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   19.00   71.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 104

#__ type_ start__ end____ width___ exp.time_
 14 omega   61.00  109.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
 15 omega   14.00   53.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 78

#__ type_ start__ end____ width___ exp.time_
 16 omega  138.00  165.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
 17 omega   40.00   90.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00  112.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 146

#__ type_ start__ end____ width___ exp.time_
 19 omega   58.00   98.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   91.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 106

#__ type_ start__ end____ width___ exp.time_
 21 omega   61.00   87.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 22 omega  101.00  128.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
 23 omega   98.00  176.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 156

#__ type_ start__ end____ width___ exp.time_
 24 omega   38.00  105.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 134

#__ type_ start__ end____ width___ exp.time_
 25 omega  102.00  162.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 120

#__ type_ start__ end____ width___ exp.time_
 26 omega   53.00   79.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 27 omega  104.00  169.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0110716000
_diffrn_orient_matrix_UB_12      -0.1754274000
_diffrn_orient_matrix_UB_13      -0.0014080000
_diffrn_orient_matrix_UB_21      -0.0721539000
_diffrn_orient_matrix_UB_22      0.0248732000
_diffrn_orient_matrix_UB_23      -0.0272608000
_diffrn_orient_matrix_UB_31      0.0145597000
_diffrn_orient_matrix_UB_32      -0.0101716000
_diffrn_orient_matrix_UB_33      -0.0428790000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3872
_reflns_number_total             5221
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         3.966
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.262
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.354
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2465
_refine_ls_R_factor_gt           0.2308
_refine_ls_restrained_S_all      2.354
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5210
_refine_ls_wR_factor_ref         0.5449
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C10(H10), C12(H12), C16(H16), C17(H17), C18(H18),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), N1(H1A)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.3002(3) 0.1572(7) 0.3490(2) 0.0692(15) Uani 1 1 d . . . . .
C2 C 0.3985(3) 0.0906(8) 0.41934(19) 0.0748(16) Uani 1 1 d . . . . .
C3 C 0.3662(3) 0.1977(7) 0.38444(18) 0.0656(14) Uani 1 1 d . . . . .
C4 C 0.3941(3) 0.3355(7) 0.38363(19) 0.0687(14) Uani 1 1 d . . . . .
H4 H 0.3737 0.4044 0.3609 0.082 Uiso 1 1 calc R . . . .
C5 C 0.4546(3) 0.3779(8) 0.4171(2) 0.0713(15) Uani 1 1 d . . . . .
C6 C 0.4845(3) 0.2740(8) 0.4499(2) 0.0731(16) Uani 1 1 d . . . . .
C7 C 0.5414(3) 0.3017(9) 0.4839(2) 0.0778(17) Uani 1 1 d . . . . .
H7 H 0.5594 0.2288 0.5059 0.093 Uiso 1 1 calc R . . . .
C8 C 0.5714(4) 0.4423(10) 0.4845(2) 0.0844(19) Uani 1 1 d . . . . .
C9 C 0.5428(4) 0.5498(11) 0.4510(3) 0.098(2) Uani 1 1 d . . . . .
H9 H 0.5629 0.6441 0.4515 0.118 Uiso 1 1 calc R . . . .
C10 C 0.4855(4) 0.5179(10) 0.4175(3) 0.092(2) Uani 1 1 d . . . . .
H10 H 0.4674 0.5893 0.3950 0.111 Uiso 1 1 calc R . . . .
C11 C 0.2474(3) 0.2250(10) 0.3640(2) 0.0830(19) Uani 1 1 d . . . . .
C12 C 0.2500(3) 0.3135(8) 0.2770(2) 0.0701(15) Uani 1 1 d . . . . .
H12 H 0.2182 0.3637 0.2843 0.084 Uiso 1 1 calc R . . . .
C13 C 0.2943(3) 0.2158(7) 0.30364(18) 0.0609(13) Uani 1 1 d . . . . .
C14 C 0.3344(3) 0.1646(6) 0.27976(18) 0.0624(13) Uani 1 1 d . . . . .
C15 C 0.3097(3) 0.2380(7) 0.23829(19) 0.0679(14) Uani 1 1 d . . . . .
C16 C 0.3353(4) 0.2164(9) 0.2055(2) 0.0829(19) Uani 1 1 d . . . . .
H16 H 0.3174 0.2634 0.1780 0.099 Uiso 1 1 calc R . . . .
C17 C 0.3882(4) 0.1228(10) 0.2156(3) 0.092(2) Uani 1 1 d . . . . .
H17 H 0.4073 0.1080 0.1947 0.111 Uiso 1 1 calc R . . . .
C18 C 0.4148(4) 0.0466(9) 0.2573(3) 0.0844(19) Uani 1 1 d . . . . .
H18 H 0.4502 -0.0185 0.2630 0.101 Uiso 1 1 calc R . . . .
C19 C 0.3880(3) 0.0702(7) 0.2887(2) 0.0699(15) Uani 1 1 d . . . . .
C20 C 0.4739(3) -0.0691(8) 0.3443(3) 0.0822(18) Uani 1 1 d . . . . .
H20A H 0.4902 -0.0762 0.3763 0.099 Uiso 1 1 calc R . . . .
H20B H 0.5038 -0.0065 0.3359 0.099 Uiso 1 1 calc R . . . .
C21 C 0.4712(3) -0.2294(8) 0.3250(2) 0.0751(16) Uani 1 1 d . . . . .
C22 C 0.4137(4) -0.3098(10) 0.3068(3) 0.091(2) Uani 1 1 d . . . . .
H22 H 0.3751 -0.2625 0.3047 0.109 Uiso 1 1 calc R . . . .
C23 C 0.4128(5) -0.4546(10) 0.2921(3) 0.101(3) Uani 1 1 d . . . . .
H23 H 0.3735 -0.5061 0.2805 0.121 Uiso 1 1 calc R . . . .
C24 C 0.4681(7) -0.5282(12) 0.2938(4) 0.126(4) Uani 1 1 d . . . . .
H24 H 0.4671 -0.6286 0.2837 0.151 Uiso 1 1 calc R . . . .
C25 C 0.5288(6) -0.4434(13) 0.3122(4) 0.118(3) Uani 1 1 d . . . . .
H25 H 0.5675 -0.4889 0.3138 0.142 Uiso 1 1 calc R . . . .
C26 C 0.5281(4) -0.2993(10) 0.3269(3) 0.096(2) Uani 1 1 d . . . . .
H26 H 0.5667 -0.2454 0.3387 0.115 Uiso 1 1 calc R . . . .
C27 C 0.6618(4) 0.3749(13) 0.5485(3) 0.112(3) Uani 1 1 d . . . . .
H27A H 0.7018 0.4183 0.5677 0.168 Uiso 1 1 calc GR . . . .
H27B H 0.6705 0.2851 0.5343 0.168 Uiso 1 1 calc GR . . . .
H27C H 0.6357 0.3466 0.5653 0.168 Uiso 1 1 calc GR . . . .
F1 F 0.1883(2) 0.1888(7) 0.33754(16) 0.1034(16) Uani 1 1 d . . . . .
F2 F 0.2493(2) 0.3799(6) 0.36549(16) 0.0983(14) Uani 1 1 d . . . . .
F3 F 0.2537(3) 0.1770(7) 0.40424(16) 0.1097(17) Uani 1 1 d . . . . .
N1 N 0.2590(3) 0.3273(6) 0.23800(17) 0.0713(13) Uani 1 1 d . . . . .
H1A H 0.2361 0.3840 0.2163 0.086 Uiso 1 1 calc R . . . .
O1 O 0.2886(2) -0.0030(5) 0.34635(14) 0.0759(12) Uani 1 1 d . . . . .
H1 H 0.2946 -0.0377 0.3246 0.114 Uiso 1 1 calc GR . . . .
O2 O 0.3795(3) -0.0368(7) 0.42391(18) 0.1006(19) Uani 1 1 d . . . . .
O3 O 0.4553(2) 0.1326(6) 0.45067(15) 0.0811(13) Uani 1 1 d . . . . .
O4 O 0.6276(3) 0.4873(7) 0.5154(2) 0.1027(18) Uani 1 1 d . . . . .
O5 O 0.4114(2) 0.0052(6) 0.32962(14) 0.0777(13) 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 C3 1.542(8) . ?
C1 C11 1.535(10) . ?
C1 C13 1.521(8) . ?
C1 O1 1.411(7) . ?
C2 C3 1.442(9) . ?
C2 O2 1.212(8) . ?
C2 O3 1.355(8) . ?
C3 C4 1.352(9) . ?
C4 C5 1.439(9) . ?
C5 C6 1.370(10) . ?
C5 C10 1.394(10) . ?
C6 C7 1.367(9) . ?
C6 O3 1.393(8) . ?
C7 C8 1.387(11) . ?
C8 C9 1.400(12) . ?
C8 O4 1.347(8) . ?
C9 C10 1.371(10) . ?
C11 F1 1.321(8) . ?
C11 F2 1.346(10) . ?
C11 F3 1.331(9) . ?
C12 C13 1.350(9) . ?
C12 N1 1.358(8) . ?
C13 C14 1.444(8) . ?
C14 C15 1.410(8) . ?
C14 C19 1.386(9) . ?
C15 C16 1.388(10) . ?
C15 N1 1.362(9) . ?
C16 C17 1.366(11) . ?
C17 C18 1.430(10) . ?
C18 C19 1.368(10) . ?
C19 O5 1.363(7) . ?
C20 C21 1.518(11) . ?
C20 O5 1.445(8) . ?
C21 C22 1.385(11) . ?
C21 C26 1.381(11) . ?
C22 C23 1.342(13) . ?
C23 C24 1.367(17) . ?
C24 C25 1.459(17) . ?
C25 C26 1.341(13) . ?
C27 O4 1.448(12) . ?

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
C11 C1 C3 107.7(5) . . ?
C13 C1 C3 111.9(5) . . ?
C13 C1 C11 111.6(6) . . ?
O1 C1 C3 112.0(5) . . ?
O1 C1 C11 104.8(5) . . ?
O1 C1 C13 108.6(5) . . ?
O2 C2 C3 126.1(6) . . ?
O2 C2 O3 115.1(6) . . ?
O3 C2 C3 118.8(6) . . ?
C2 C3 C1 120.5(5) . . ?
C4 C3 C1 120.4(5) . . ?
C4 C3 C2 119.0(5) . . ?
C3 C4 C5 121.4(6) . . ?
C6 C5 C4 118.5(6) . . ?
C6 C5 C10 118.0(6) . . ?
C10 C5 C4 123.4(6) . . ?
C5 C6 O3 119.8(6) . . ?
C7 C6 C5 124.0(6) . . ?
C7 C6 O3 116.1(6) . . ?
C6 C7 C8 117.7(7) . . ?
C7 C8 C9 119.7(6) . . ?
O4 C8 C7 125.2(7) . . ?
O4 C8 C9 115.1(7) . . ?
C10 C9 C8 120.9(8) . . ?
C9 C10 C5 119.6(8) . . ?
F1 C11 C1 113.2(6) . . ?
F1 C11 F2 105.8(7) . . ?
F1 C11 F3 107.1(6) . . ?
F2 C11 C1 112.2(6) . . ?
F3 C11 C1 111.5(7) . . ?
F3 C11 F2 106.7(6) . . ?
C13 C12 N1 109.6(6) . . ?
C12 C13 C1 128.3(5) . . ?
C12 C13 C14 107.3(5) . . ?
C14 C13 C1 124.3(5) . . ?
C15 C14 C13 105.7(5) . . ?
C19 C14 C13 135.8(5) . . ?
C19 C14 C15 118.5(6) . . ?
C16 C15 C14 123.0(6) . . ?
N1 C15 C14 107.5(5) . . ?
N1 C15 C16 129.4(6) . . ?
C17 C16 C15 116.7(6) . . ?
C16 C17 C18 121.9(6) . . ?
C19 C18 C17 119.6(7) . . ?
C18 C19 C14 120.1(6) . . ?
O5 C19 C14 116.5(5) . . ?
O5 C19 C18 123.3(6) . . ?
O5 C20 C21 112.5(6) . . ?
C22 C21 C20 122.2(7) . . ?
C26 C21 C20 119.0(7) . . ?
C26 C21 C22 118.8(8) . . ?
C23 C22 C21 121.3(9) . . ?
C22 C23 C24 121.6(9) . . ?
C23 C24 C25 117.5(9) . . ?
C26 C25 C24 119.3(10) . . ?
C25 C26 C21 121.4(9) . . ?
C12 N1 C15 109.9(5) . . ?
C2 O3 C6 122.4(5) . . ?
C8 O4 C27 117.1(7) . . ?
C19 O5 C20 119.4(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
