# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_sf20190530a_0m
_database_code_depnum_ccdc_archive 'CCDC 2008773'
loop_
_audit_author_name
_audit_author_address
'Feng Shi'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2020-06-09 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2019-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H20 F3 N O2'
_chemical_formula_sum            'C29 H20 F3 N O2'
_chemical_formula_weight         471.46
_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'
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'

_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                   10.333(4)
_cell_length_b                   10.460(4)
_cell_length_c                   11.583(5)
_cell_angle_alpha                88.838(5)
_cell_angle_beta                 68.455(5)
_cell_angle_gamma                79.684(6)
_cell_volume                     1144.2(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1508
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.369
_cell_measurement_theta_min      2.646
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0592 before and 0.0299 after correction.
The Ratio of minimum to maximum transmission is 0.9142.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_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  0.0168
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6041
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_min         2.672
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2817
_reflns_number_total             4240
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    ?
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0797P)²+0.2071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1617
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H17(0.5) H23(0.5) O2(0.5) H2(0.5) O2A(0.5) H2A(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F1 F -0.1767(2) 0.4468(2) 0.23446(18) 0.0947(7) Uani 1 1 d . . . . .
F2 F -0.1522(2) 0.34677(19) 0.3894(2) 0.1030(7) Uani 1 1 d . . . . .
F3 F -0.35579(18) 0.43928(18) 0.40017(19) 0.0840(6) Uani 1 1 d . . . . .
O1 O -0.3025(2) 0.6189(2) 0.50806(18) 0.0638(6) Uani 1 1 d . . . . .
N1 N 0.0320(2) 0.80480(18) 0.29857(18) 0.0403(5) Uani 1 1 d . . . . .
C1 C 0.2687(2) 0.6950(2) 0.1323(2) 0.0401(6) Uani 1 1 d . . . . .
H1 H 0.311630 0.602597 0.114742 0.048 Uiso 1 1 calc R . . . .
C2 C 0.1201(2) 0.6960(2) 0.2233(2) 0.0394(6) Uani 1 1 d . . . . .
C3 C 0.0501(3) 0.5939(2) 0.2535(2) 0.0411(6) Uani 1 1 d . . . . .
C4 C -0.0848(3) 0.6373(2) 0.3509(2) 0.0417(6) Uani 1 1 d . . . . .
C5 C -0.0928(3) 0.7700(2) 0.3792(2) 0.0417(6) Uani 1 1 d . . . . .
C6 C -0.1956(3) 0.8661(3) 0.4611(2) 0.0500(7) Uani 1 1 d . . . . .
H6 H -0.279436 0.845112 0.516488 0.060 Uiso 1 1 calc R . . . .
C7 C -0.1727(3) 0.9902(3) 0.4596(3) 0.0532(7) Uani 1 1 d . . . . .
H7 H -0.240637 1.053887 0.514811 0.064 Uiso 1 1 calc R . . . .
C8 C -0.0471(3) 1.0226(3) 0.3752(3) 0.0526(7) Uani 1 1 d . . . . .
H8 H -0.032803 1.107969 0.373860 0.063 Uiso 1 1 calc R . . . .
C9 C 0.0530(3) 0.9306(2) 0.2960(3) 0.0474(6) Uani 1 1 d . . . . .
H9 H 0.136028 0.952540 0.239987 0.057 Uiso 1 1 calc R . . . .
C10 C -0.2046(3) 0.5756(3) 0.4126(2) 0.0456(6) Uani 1 1 d . . . . .
C11 C -0.2210(3) 0.4510(3) 0.3556(3) 0.0615(8) Uani 1 1 d . . . . .
C12 C 0.3596(2) 0.7511(2) 0.1902(2) 0.0408(6) Uani 1 1 d . . . . .
C13 C 0.4109(3) 0.8640(3) 0.1529(3) 0.0498(7) Uani 1 1 d . . . . .
H13 H 0.391281 0.908177 0.089054 0.060 Uiso 1 1 calc R . . . .
C14 C 0.4910(3) 0.9131(3) 0.2083(3) 0.0615(8) Uani 1 1 d . . . . .
H14 H 0.523327 0.990227 0.182698 0.074 Uiso 1 1 calc R . . . .
C15 C 0.5223(3) 0.8474(3) 0.3012(3) 0.0652(8) Uani 1 1 d . . . . .
H15 H 0.575736 0.880317 0.338844 0.078 Uiso 1 1 calc R . . . .
C16 C 0.4752(3) 0.7332(3) 0.3387(3) 0.0658(8) Uani 1 1 d . . . . .
H16 H 0.497473 0.688295 0.401080 0.079 Uiso 1 1 calc R . . . .
C17 C 0.3944(3) 0.6850(3) 0.2833(3) 0.0527(7) Uani 1 1 d . . . . .
H17 H 0.363075 0.607445 0.308625 0.063 Uiso 0.5 1 calc R . P A 2
C18 C 0.2792(3) 0.7471(2) 0.0066(2) 0.0417(6) Uani 1 1 d . . . . .
C19 C 0.1695(3) 0.8283(3) -0.0134(3) 0.0625(8) Uani 1 1 d . . . . .
H19 H 0.084021 0.854181 0.052583 0.075 Uiso 1 1 calc R . . . .
C20 C 0.1853(4) 0.8721(3) -0.1310(3) 0.0758(10) Uani 1 1 d . . . . .
H20 H 0.110889 0.927820 -0.143015 0.091 Uiso 1 1 calc R . . . .
C21 C 0.3089(4) 0.8339(3) -0.2285(3) 0.0666(9) Uani 1 1 d . . . . .
H21 H 0.318964 0.864101 -0.306876 0.080 Uiso 1 1 calc R . . . .
C22 C 0.4189(3) 0.7510(3) -0.2122(3) 0.0613(8) Uani 1 1 d . . . . .
H22 H 0.503071 0.723938 -0.279362 0.074 Uiso 1 1 calc R . . . .
C23 C 0.4038(3) 0.7082(3) -0.0952(3) 0.0531(7) Uani 1 1 d . . . . .
H23 H 0.478646 0.652020 -0.084303 0.064 Uiso 0.5 1 calc R . P B 1
C24 C 0.1142(2) 0.4617(2) 0.1941(2) 0.0416(6) Uani 1 1 d . . . . .
C25 C 0.1416(3) 0.4382(3) 0.0693(3) 0.0578(7) Uani 1 1 d . . . . .
H25 H 0.120913 0.506221 0.022189 0.069 Uiso 1 1 calc R . . . .
C26 C 0.1989(4) 0.3152(3) 0.0141(3) 0.0744(9) Uani 1 1 d . . . . .
H26 H 0.214756 0.300211 -0.069227 0.089 Uiso 1 1 calc R . . . .
C27 C 0.2329(4) 0.2145(3) 0.0824(3) 0.0731(9) Uani 1 1 d . . . . .
H27 H 0.271152 0.131356 0.045324 0.088 Uiso 1 1 calc R . . . .
C28 C 0.2105(3) 0.2367(3) 0.2042(3) 0.0639(8) Uani 1 1 d . . . . .
H28 H 0.234826 0.168811 0.249734 0.077 Uiso 1 1 calc R . . . .
C29 C 0.1520(3) 0.3593(3) 0.2604(3) 0.0520(7) Uani 1 1 d . . . . .
H29 H 0.137648 0.373474 0.343533 0.062 Uiso 1 1 calc R . . . .
O2 O 0.3517(4) 0.5632(3) 0.3071(3) 0.0458(8) Uani 0.5 1 d . . P C 1
H2 H 0.378957 0.528297 0.360263 0.069 Uiso 0.5 1 calc GR . P C 1
O2A O 0.5037(5) 0.6156(5) -0.0790(4) 0.0823(14) Uani 0.5 1 d . . P D 2
H2A H 0.483594 0.604703 -0.004617 0.123 Uiso 0.5 1 calc GR . P D 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
F1 C11 1.306(4) . ?
F2 C11 1.325(4) . ?
F3 C11 1.323(3) . ?
O1 C10 1.218(3) . ?
N1 C2 1.404(3) . ?
N1 C5 1.392(3) . ?
N1 C9 1.370(3) . ?
C1 C2 1.508(3) . ?
C1 C12 1.534(3) . ?
C1 C18 1.517(3) . ?
C2 C3 1.365(3) . ?
C3 C4 1.435(3) . ?
C3 C24 1.483(3) . ?
C4 C5 1.413(3) . ?
C4 C10 1.442(3) . ?
C5 C6 1.397(3) . ?
C6 C7 1.359(4) . ?
C7 C8 1.403(4) . ?
C8 C9 1.349(4) . ?
C10 C11 1.536(4) . ?
C12 C13 1.377(3) . ?
C12 C17 1.391(3) . ?
C13 C14 1.384(4) . ?
C14 C15 1.371(4) . ?
C15 C16 1.373(4) . ?
C16 C17 1.386(4) . ?
C17 O2 1.412(4) . ?
C18 C19 1.378(4) . ?
C18 C23 1.390(4) . ?
C19 C20 1.390(4) . ?
C20 C21 1.357(5) . ?
C21 C22 1.370(4) . ?
C22 C23 1.381(4) . ?
C23 O2A 1.346(5) . ?
C24 C25 1.386(4) . ?
C24 C29 1.388(4) . ?
C25 C26 1.376(4) . ?
C26 C27 1.377(4) . ?
C27 C28 1.360(5) . ?
C28 C29 1.378(4) . ?

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
C5 N1 C2 109.77(19) . . ?
C9 N1 C2 128.8(2) . . ?
C9 N1 C5 121.3(2) . . ?
C2 C1 C12 112.6(2) . . ?
C2 C1 C18 115.1(2) . . ?
C18 C1 C12 113.75(19) . . ?
N1 C2 C1 124.4(2) . . ?
C3 C2 N1 107.8(2) . . ?
C3 C2 C1 127.8(2) . . ?
C2 C3 C4 108.6(2) . . ?
C2 C3 C24 122.3(2) . . ?
C4 C3 C24 129.0(2) . . ?
C3 C4 C10 133.0(2) . . ?
C5 C4 C3 107.1(2) . . ?
C5 C4 C10 119.8(2) . . ?
N1 C5 C4 106.7(2) . . ?
N1 C5 C6 118.4(2) . . ?
C6 C5 C4 134.8(2) . . ?
C7 C6 C5 119.9(3) . . ?
C6 C7 C8 120.2(3) . . ?
C9 C8 C7 120.4(3) . . ?
C8 C9 N1 119.7(2) . . ?
O1 C10 C4 124.3(3) . . ?
O1 C10 C11 114.8(2) . . ?
C4 C10 C11 120.8(2) . . ?
F1 C11 F2 108.2(3) . . ?
F1 C11 F3 108.5(3) . . ?
F1 C11 C10 114.0(2) . . ?
F2 C11 C10 110.6(3) . . ?
F3 C11 F2 105.7(2) . . ?
F3 C11 C10 109.5(2) . . ?
C13 C12 C1 122.9(2) . . ?
C13 C12 C17 117.9(2) . . ?
C17 C12 C1 119.2(2) . . ?
C12 C13 C14 121.5(3) . . ?
C15 C14 C13 119.6(3) . . ?
C14 C15 C16 120.3(3) . . ?
C15 C16 C17 119.7(3) . . ?
C12 C17 O2 114.8(3) . . ?
C16 C17 C12 120.9(3) . . ?
C16 C17 O2 124.1(3) . . ?
C19 C18 C1 123.5(2) . . ?
C19 C18 C23 117.7(2) . . ?
C23 C18 C1 118.8(2) . . ?
C18 C19 C20 120.8(3) . . ?
C21 C20 C19 120.3(3) . . ?
C20 C21 C22 120.4(3) . . ?
C21 C22 C23 119.4(3) . . ?
C22 C23 C18 121.5(3) . . ?
O2A C23 C18 117.6(3) . . ?
O2A C23 C22 120.5(3) . . ?
C25 C24 C3 120.5(2) . . ?
C25 C24 C29 118.1(2) . . ?
C29 C24 C3 121.3(2) . . ?
C26 C25 C24 120.8(3) . . ?
C25 C26 C27 120.0(3) . . ?
C28 C27 C26 120.0(3) . . ?
C27 C28 C29 120.4(3) . . ?
C28 C29 C24 120.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
