# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1939449'
loop_
_audit_author_name
_audit_author_address
'Yunhe Lv'
;Anyang Normal University
China
;
_audit_update_record             
;
2019-07-09 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H25 F N2 O5'
_chemical_formula_weight         512.52

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0079(5)
_cell_length_b                   11.0103(5)
_cell_length_c                   13.8154(7)
_cell_angle_alpha                68.117(3)
_cell_angle_beta                 74.662(4)
_cell_angle_gamma                67.141(3)
_cell_volume                     1288.87(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3348
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      22.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13223
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.465
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4505
_reflns_number_gt                3297
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2017 (Sheldrick 2017)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0936P)²+0.8309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4505
_refine_ls_number_parameters     344
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1960
_refine_ls_wR_factor_gt          0.1798
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.256
_refine_ls_shift/su_max          0.001
_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_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 0.24952(18) 0.58176(18) 0.20510(13) 0.0547(5) Uani 1 1 d . . . . .
O5 O 0.5724(2) 0.1862(2) 0.36708(19) 0.0550(6) Uani 1 1 d . . . . .
O2 O 0.6220(2) 0.4151(2) 0.15320(17) 0.0562(6) Uani 1 1 d . . . . .
N1 N 0.7777(2) 0.2238(2) 0.37109(18) 0.0411(6) Uani 1 1 d . . . . .
H1A H 0.807689 0.286104 0.373024 0.049 Uiso 1 1 calc R U . . .
C18 C 1.1494(3) -0.0318(3) 0.3583(2) 0.0394(6) Uani 1 1 d . . . . .
C17 C 1.0324(3) 0.0920(3) 0.3603(2) 0.0357(6) Uani 1 1 d . . . . .
C9 C 0.6315(3) 0.2607(3) 0.3715(2) 0.0391(6) Uani 1 1 d . . . . .
C10 C 0.8866(3) 0.0968(3) 0.3679(2) 0.0365(6) Uani 1 1 d . . . . .
C4 C 0.4407(3) 0.6641(3) 0.1827(2) 0.0470(7) Uani 1 1 d . . . . .
C11 C 0.8605(3) -0.0187(3) 0.3726(3) 0.0490(7) Uani 1 1 d . . . . .
H11A H 0.765050 -0.016417 0.377702 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3968(3) 0.4666(3) 0.3435(2) 0.0383(6) Uani 1 1 d . . . . .
C19 C 0.2475(3) 0.4122(3) 0.5232(2) 0.0392(6) Uani 1 1 d . . . . .
C1 C 0.2707(3) 0.4697(3) 0.4078(2) 0.0382(6) Uani 1 1 d . . . . .
H1B H 0.186536 0.513904 0.375473 0.046 Uiso 1 1 calc R U . . .
C20 C 0.3246(3) 0.2779(3) 0.5782(2) 0.0441(7) Uani 1 1 d . . . . .
H20A H 0.396480 0.220718 0.541504 0.053 Uiso 1 1 calc R U . . .
C30 C 0.1387(3) 0.4935(3) 0.5809(2) 0.0451(7) Uani 1 1 d . . . . .
H30A H 0.083229 0.582080 0.545636 0.054 Uiso 1 1 calc R U . . .
C13 C 1.1181(3) -0.1480(3) 0.3634(2) 0.0489(7) Uani 1 1 d . . . . .
H13A H 1.193812 -0.230271 0.362570 0.059 Uiso 1 1 calc R U . . .
C3 C 0.3919(3) 0.5348(3) 0.2262(2) 0.0416(7) Uani 1 1 d . . . . .
C21 C 0.2958(3) 0.2291(3) 0.6861(2) 0.0488(7) Uani 1 1 d . . . . .
H21A H 0.347984 0.139028 0.721166 0.059 Uiso 1 1 calc R U . . .
C8 C 0.5455(3) 0.4056(3) 0.3802(2) 0.0408(6) Uani 1 1 d . . . . .
H8A H 0.532249 0.402593 0.453114 0.049 Uiso 1 1 calc R U . . .
H8B H 0.602708 0.466325 0.338833 0.049 Uiso 1 1 calc R U . . .
C29 C 0.1117(3) 0.4455(3) 0.6889(2) 0.0513(8) Uani 1 1 d . . . . .
H29A H 0.040198 0.502913 0.725628 0.062 Uiso 1 1 calc R U . . .
C12 C 0.9781(3) -0.1407(3) 0.3696(3) 0.0548(8) Uani 1 1 d . . . . .
H12A H 0.959257 -0.218117 0.371977 0.066 Uiso 1 1 calc R U . . .
C28 C 0.1896(3) 0.3122(3) 0.7440(2) 0.0511(7) Uani 1 1 d . U . . .
C14 C 1.2918(3) -0.0314(3) 0.3502(3) 0.0513(8) Uani 1 1 d . . . . .
H14A H 1.371323 -0.111222 0.349424 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4807(4) 0.4327(3) 0.1632(2) 0.0494(7) Uani 1 1 d . . . . .
C16 C 1.1906(4) 0.2036(4) 0.3454(3) 0.0686(10) Uani 1 1 d . . . . .
H16A H 1.206815 0.283521 0.340381 0.082 Uiso 1 1 calc R U . . .
C15 C 1.3128(4) 0.0860(4) 0.3437(3) 0.0685(10) Uani 1 1 d . . . . .
H15A H 1.406580 0.088125 0.338154 0.082 Uiso 1 1 calc R U . . .
C27 C 0.1606(4) 0.2628(4) 0.8598(3) 0.0718(8) Uani 1 1 d . U . . .
C22 C 0.1483(5) 0.1329(5) 0.9112(4) 0.0927(11) Uani 1 1 d . U . . .
H22A H 0.155746 0.075622 0.873380 0.111 Uiso 1 1 calc R U . . .
C5 C 0.4808(5) 0.8382(4) 0.0264(3) 0.0851(13) Uani 1 1 d . . . . .
H5A H 0.473708 0.866464 -0.047241 0.128 Uiso 1 1 calc R U . . .
H5B H 0.417741 0.911461 0.055393 0.128 Uiso 1 1 calc R U . . .
H5C H 0.580132 0.817627 0.035099 0.128 Uiso 1 1 calc R U . . .
C24 C 0.1160(6) 0.1771(7) 1.0717(5) 0.1135(13) Uani 1 1 d . U . . .
H24A H 0.101252 0.147165 1.144947 0.136 Uiso 1 1 calc R U . . .
C23 C 0.1232(6) 0.0869(6) 1.0265(4) 0.1137(13) Uani 1 1 d . U . . .
H23A H 0.113061 0.000760 1.065358 0.136 Uiso 1 1 calc R U . . .
C7 C 0.7222(5) 0.3159(5) 0.0990(3) 0.0864(13) Uani 1 1 d . . . . .
H7A H 0.821014 0.310988 0.096029 0.130 Uiso 1 1 calc R U . . .
H7B H 0.711664 0.226401 0.136501 0.130 Uiso 1 1 calc R U . . .
H7C H 0.699922 0.344896 0.028752 0.130 Uiso 1 1 calc R U . . .
C26 C 0.1476(5) 0.3461(5) 0.9186(3) 0.0914(10) Uani 1 1 d . U . . .
H26A H 0.153185 0.434685 0.883325 0.110 Uiso 1 1 calc R U . . .
C25 C 0.1265(6) 0.3021(6) 1.0289(4) 0.1111(12) Uani 1 1 d . U . . .
H25A H 0.120486 0.356679 1.068523 0.133 Uiso 1 1 calc R U . . .
N2 N 1.0547(3) 0.2096(2) 0.3536(2) 0.0500(6) Uani 1 1 d . . . . .
O4 O 0.4370(3) 0.7162(2) 0.08042(18) 0.0693(7) Uani 1 1 d . . . . .
O3 O 0.4729(3) 0.7099(2) 0.2352(2) 0.0689(7) Uani 1 1 d . . . . .
O1 O 0.4279(3) 0.3791(3) 0.1299(2) 0.0760(7) 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
F1 C3 1.384(3) . ?
O5 C9 1.209(3) . ?
O2 C6 1.326(4) . ?
O2 C7 1.456(4) . ?
N1 C9 1.357(3) . ?
N1 C10 1.408(3) . ?
C18 C14 1.401(4) . ?
C18 C17 1.415(4) . ?
C18 C13 1.404(4) . ?
C17 N2 1.363(3) . ?
C17 C10 1.417(4) . ?
C9 C8 1.524(4) . ?
C10 C11 1.370(4) . ?
C4 O3 1.186(4) . ?
C4 O4 1.316(4) . ?
C4 C3 1.541(4) . ?
C11 C12 1.407(4) . ?
C2 C1 1.334(4) . ?
C2 C8 1.514(4) . ?
C2 C3 1.517(4) . ?
C19 C20 1.395(4) . ?
C19 C30 1.392(4) . ?
C19 C1 1.470(4) . ?
C20 C21 1.374(4) . ?
C30 C29 1.374(4) . ?
C13 C12 1.352(4) . ?
C3 C6 1.534(4) . ?
C21 C28 1.395(4) . ?
C29 C28 1.391(4) . ?
C28 C27 1.472(5) . ?
C14 C15 1.356(4) . ?
C6 O1 1.188(4) . ?
C16 N2 1.312(4) . ?
C16 C15 1.396(5) . ?
C27 C22 1.377(6) . ?
C27 C26 1.388(6) . ?
C22 C23 1.465(7) . ?
C5 O4 1.445(4) . ?
C24 C25 1.315(8) . ?
C24 C23 1.327(8) . ?
C26 C25 1.400(6) . ?

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
C6 O2 C7 116.2(3) . . ?
C9 N1 C10 128.4(2) . . ?
C14 C18 C17 117.8(2) . . ?
C14 C18 C13 123.3(3) . . ?
C17 C18 C13 118.9(2) . . ?
N2 C17 C18 122.2(2) . . ?
N2 C17 C10 118.0(2) . . ?
C18 C17 C10 119.8(2) . . ?
O5 C9 N1 124.0(2) . . ?
O5 C9 C8 122.1(2) . . ?
N1 C9 C8 113.9(2) . . ?
C11 C10 N1 124.9(2) . . ?
C11 C10 C17 119.5(2) . . ?
N1 C10 C17 115.6(2) . . ?
O3 C4 O4 126.1(3) . . ?
O3 C4 C3 124.2(3) . . ?
O4 C4 C3 109.6(2) . . ?
C10 C11 C12 120.0(3) . . ?
C1 C2 C8 124.3(3) . . ?
C1 C2 C3 118.4(2) . . ?
C8 C2 C3 117.2(2) . . ?
C20 C19 C30 117.8(3) . . ?
C20 C19 C1 123.5(2) . . ?
C30 C19 C1 118.6(2) . . ?
C2 C1 C19 128.4(2) . . ?
C21 C20 C19 120.8(3) . . ?
C29 C30 C19 121.3(3) . . ?
C12 C13 C18 120.2(3) . . ?
F1 C3 C2 110.2(2) . . ?
F1 C3 C6 105.9(2) . . ?
C2 C3 C6 112.0(2) . . ?
F1 C3 C4 105.1(2) . . ?
C2 C3 C4 112.7(2) . . ?
C6 C3 C4 110.5(2) . . ?
C20 C21 C28 121.3(3) . . ?
C2 C8 C9 114.1(2) . . ?
C30 C29 C28 120.9(3) . . ?
C13 C12 C11 121.5(3) . . ?
C29 C28 C21 117.8(3) . . ?
C29 C28 C27 120.3(3) . . ?
C21 C28 C27 121.9(3) . . ?
C15 C14 C18 119.6(3) . . ?
O1 C6 O2 126.7(3) . . ?
O1 C6 C3 123.9(3) . . ?
O2 C6 C3 109.3(2) . . ?
N2 C16 C15 124.8(3) . . ?
C14 C15 C16 118.5(3) . . ?
C22 C27 C26 119.2(4) . . ?
C22 C27 C28 120.7(4) . . ?
C26 C27 C28 120.1(4) . . ?
C27 C22 C23 118.7(5) . . ?
C25 C24 C23 130.0(6) . . ?
C24 C23 C22 115.2(6) . . ?
C25 C26 C27 122.6(5) . . ?
C24 C25 C26 114.4(6) . . ?
C16 N2 C17 117.1(3) . . ?
C4 O4 C5 117.0(3) . . ?

_refine_diff_density_max         0.807
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.052
