# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_cu_2021524_0m
_database_code_depnum_ccdc_archive 'CCDC 2084340'
loop_
_audit_author_name
_audit_author_address
APf
;shanghai institute of material medical
China
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_audit_creation_date             2021-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 F N O3'
_chemical_formula_sum            'C10 H12 F N O3'
_chemical_formula_weight         213.21
_chemical_absolute_configuration rmad
_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 0.0181 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.93840(10)
_cell_length_b                   5.30530(10)
_cell_length_c                   15.9518(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.2890(10)
_cell_angle_gamma                90
_cell_volume                     501.734(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4835
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.544
_cell_measurement_theta_min      2.775
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1097 before and 0.0639 after correction. The Ratio of minimum to maximum transmission is 0.8794. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5180
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        63.685
_diffrn_reflns_theta_max         63.685
_diffrn_reflns_theta_min         2.775
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                1564
_reflns_number_total             1596
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1596
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.095
_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)+(0.0365P)²+0.0545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0676
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C6'(H6'), C4'(H4'), C5'(H5')
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O2 O -0.0223(2) 0.9423(3) 0.62711(9) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.6370(2) 0.6146(3) 0.64596(9) 0.0289(4) Uani 1 1 d . . . . .
H3 H 0.744078 0.717739 0.651780 0.043 Uiso 1 1 calc GR . . . .
O1 O 0.2556(2) 0.9381(3) 0.53872(9) 0.0295(4) Uani 1 1 d . . . . .
F1 F 1.0105(3) 0.0564(3) 0.86270(9) 0.0524(4) Uani 1 1 d . . . . .
N1 N 0.2992(3) 0.4450(4) 0.53809(11) 0.0223(4) Uani 1 1 d . . . . .
C1 C 0.1308(3) 0.8356(4) 0.58973(12) 0.0213(4) Uani 1 1 d . . . . .
C1' C 0.6085(3) 0.5368(5) 0.79520(13) 0.0270(5) Uani 1 1 d . . . . .
C2 C 0.1651(3) 0.5536(4) 0.60541(12) 0.0212(4) Uani 1 1 d . . . . .
H2 H 0.013355 0.471271 0.601811 0.025 Uiso 1 1 calc R . . . .
C4 C 0.4954(3) 0.6391(4) 0.71433(12) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.458673 0.821193 0.722194 0.029 Uiso 1 1 calc R . . . .
C3 C 0.2779(3) 0.4942(4) 0.69229(12) 0.0237(5) Uani 1 1 d . . . . .
H3A H 0.169123 0.531309 0.735398 0.028 Uiso 1 1 calc R . . . .
H3B H 0.311454 0.311518 0.695083 0.028 Uiso 1 1 calc R . . . .
C2' C 0.7588(4) 0.3368(5) 0.79212(13) 0.0293(5) Uani 1 1 d . . . . .
H2' H 0.791967 0.263275 0.739946 0.035 Uiso 1 1 calc R . . . .
C6' C 0.5603(4) 0.6383(5) 0.87222(13) 0.0343(6) Uani 1 1 d . . . . .
H6' H 0.456697 0.774189 0.874628 0.041 Uiso 1 1 calc R . . . .
C3' C 0.8589(4) 0.2474(5) 0.86638(16) 0.0355(6) Uani 1 1 d . . . . .
C4' C 0.8146(4) 0.3445(6) 0.94349(14) 0.0394(6) Uani 1 1 d . . . . .
H4' H 0.885927 0.278075 0.993542 0.047 Uiso 1 1 calc R . . . .
C5' C 0.6631(4) 0.5417(6) 0.94618(14) 0.0403(6) Uani 1 1 d . . . . .
H5' H 0.628853 0.611937 0.998736 0.048 Uiso 1 1 calc R . . . .
H1A H 0.441(5) 0.493(5) 0.5464(14) 0.030(6) Uiso 1 1 d . . . . .
H1B H 0.249(4) 0.501(5) 0.4869(16) 0.025(6) Uiso 1 1 d . . . . .
H1C H 0.283(4) 0.279(7) 0.5390(16) 0.030(7) Uiso 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
O2 C1 1.251(3) . ?
O3 H3 0.8400 . ?
O3 C4 1.421(2) . ?
O1 C1 1.255(3) . ?
F1 C3' 1.359(3) . ?
N1 C2 1.489(3) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.90(3) . ?
N1 H1C 0.88(3) . ?
C1 C2 1.528(3) . ?
C1' C4 1.520(3) . ?
C1' C2' 1.389(3) . ?
C1' C6' 1.386(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.537(3) . ?
C4 H4 1.0000 . ?
C4 C3 1.526(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2' H2' 0.9500 . ?
C2' C3' 1.379(3) . ?
C6' H6' 0.9500 . ?
C6' C5' 1.394(3) . ?
C3' C4' 1.373(4) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.382(4) . ?
C5' H5' 0.9500 . ?

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
C4 O3 H3 109.5 . . ?
C2 N1 H1A 109.0(16) . . ?
C2 N1 H1B 111.5(15) . . ?
C2 N1 H1C 108.1(17) . . ?
H1A N1 H1B 108(2) . . ?
H1A N1 H1C 113(3) . . ?
H1B N1 H1C 108(2) . . ?
O2 C1 O1 125.8(2) . . ?
O2 C1 C2 117.30(18) . . ?
O1 C1 C2 116.88(19) . . ?
C2' C1' C4 119.75(19) . . ?
C6' C1' C4 120.6(2) . . ?
C6' C1' C2' 119.6(2) . . ?
N1 C2 C1 109.41(17) . . ?
N1 C2 H2 107.9 . . ?
N1 C2 C3 110.33(16) . . ?
C1 C2 H2 107.9 . . ?
C1 C2 C3 113.28(16) . . ?
C3 C2 H2 107.9 . . ?
O3 C4 C1' 111.53(16) . . ?
O3 C4 H4 109.1 . . ?
O3 C4 C3 107.90(15) . . ?
C1' C4 H4 109.1 . . ?
C1' C4 C3 110.03(17) . . ?
C3 C4 H4 109.1 . . ?
C2 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 C2 115.08(16) . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C1' C2' H2' 120.7 . . ?
C3' C2' C1' 118.6(2) . . ?
C3' C2' H2' 120.7 . . ?
C1' C6' H6' 119.9 . . ?
C1' C6' C5' 120.3(2) . . ?
C5' C6' H6' 119.9 . . ?
F1 C3' C2' 118.3(2) . . ?
F1 C3' C4' 118.7(2) . . ?
C4' C3' C2' 123.1(2) . . ?
C3' C4' H4' 121.0 . . ?
C3' C4' C5' 118.1(2) . . ?
C5' C4' H4' 121.0 . . ?
C6' C5' H5' 119.8 . . ?
C4' C5' C6' 120.4(2) . . ?
C4' C5' H5' 119.8 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
