# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_exp_12570
_database_code_depnum_ccdc_archive 'CCDC 2235475'
loop_
_audit_author_name
_audit_author_address
'HFZ-carboxylic acid'
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2023-01-11 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 F N O2'
_chemical_formula_weight         209.22

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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.2503(5)
_cell_length_b                   16.2082(13)
_cell_length_c                   12.1305(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.976(13)
_cell_angle_gamma                90
_cell_volume                     1016.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    790
_cell_measurement_theta_min      4.5720
_cell_measurement_theta_max      67.1820

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.895
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_T_min  0.85144
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3422
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.598
_diffrn_reflns_theta_max         67.249
_diffrn_reflns_theta_full        67.249
_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             1817
_reflns_number_gt                998
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0906P)²+0.1945P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1817
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2021
_refine_ls_wR_factor_gt          0.1672
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_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
N1 N 0.0486(6) 0.26068(16) 0.2369(2) 0.0716(9) Uani 1 1 d . . . . .
F1 F -0.2385(5) 0.50169(13) 0.4002(2) 0.1020(9) Uani 1 1 d . . . . .
O1 O 0.2959(7) 0.51812(15) 0.0976(3) 0.1098(11) Uani 1 1 d . . . . .
H1 H 0.390948 0.537586 0.057350 0.165 Uiso 1 1 calc R U . . .
O2 O 0.4114(6) 0.40387(15) 0.0245(2) 0.0968(10) Uani 1 1 d . . . . .
C1 C -0.2251(7) 0.4176(2) 0.3972(3) 0.0739(10) Uani 1 1 d . . . . .
C2 C -0.3514(8) 0.3736(3) 0.4661(3) 0.0870(12) Uani 1 1 d . . . . .
H2 H -0.446059 0.399498 0.514261 0.104 Uiso 1 1 calc R U . . .
C3 C -0.3335(8) 0.2900(3) 0.4617(4) 0.0880(12) Uani 1 1 d . . . . .
H3 H -0.412639 0.258031 0.509750 0.106 Uiso 1 1 calc R U . . .
C4 C -0.2002(7) 0.2516(2) 0.3874(3) 0.0744(10) Uani 1 1 d . . . . .
H4 H -0.192952 0.194265 0.385331 0.089 Uiso 1 1 calc R U . . .
C5 C -0.0763(6) 0.29796(19) 0.3154(3) 0.0611(9) Uani 1 1 d . . . . .
C6 C 0.2112(7) 0.3086(2) 0.1775(3) 0.0748(11) Uani 1 1 d . . . . .
H6A H 0.227175 0.280148 0.108610 0.090 Uiso 1 1 calc R U . . .
H6B H 0.382485 0.312208 0.222533 0.090 Uiso 1 1 calc R U . . .
C7 C 0.1135(8) 0.3927(2) 0.1500(3) 0.0798(11) Uani 1 1 d . . . . .
H7 H -0.049217 0.385654 0.097468 0.096 Uiso 1 1 calc R U . . .
C8 C 0.0443(7) 0.43961(19) 0.2481(3) 0.0683(10) Uani 1 1 d . . . . .
H8A H 0.200037 0.462646 0.292029 0.082 Uiso 1 1 calc R U . . .
H8B H -0.070146 0.484908 0.220815 0.082 Uiso 1 1 calc R U . . .
C9 C -0.0865(6) 0.38421(19) 0.3211(3) 0.0598(8) Uani 1 1 d . . . . .
C10 C 0.0906(9) 0.1724(2) 0.2395(4) 0.0909(13) Uani 1 1 d . . . . .
H10A H 0.193603 0.157169 0.309873 0.136 Uiso 1 1 calc R U . . .
H10B H 0.179116 0.156926 0.179700 0.136 Uiso 1 1 calc R U . . .
H10C H -0.072917 0.144471 0.230676 0.136 Uiso 1 1 calc R U . . .
C11 C 0.2886(7) 0.4411(2) 0.0872(3) 0.0715(10) 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
N1 C5 1.385(4) . ?
N1 C6 1.437(4) . ?
N1 C10 1.448(4) . ?
F1 C1 1.365(4) . ?
O1 C11 1.255(4) . ?
O1 H1 0.8200 . ?
O2 C11 1.236(4) . ?
C1 C2 1.356(5) . ?
C1 C9 1.381(4) . ?
C2 C3 1.360(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C9 1.401(4) . ?
C6 C7 1.474(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.508(4) . ?
C7 C11 1.512(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.508(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 C6 120.2(3) . . ?
C5 N1 C10 120.3(3) . . ?
C6 N1 C10 116.3(3) . . ?
C11 O1 H1 109.5 . . ?
C2 C1 F1 118.4(3) . . ?
C2 C1 C9 125.2(3) . . ?
F1 C1 C9 116.4(3) . . ?
C1 C2 C3 117.1(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 121.5(3) . . ?
N1 C5 C9 119.7(3) . . ?
C4 C5 C9 118.7(3) . . ?
N1 C6 C7 113.5(3) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 114.2(3) . . ?
C6 C7 C11 112.1(3) . . ?
C8 C7 C11 112.7(3) . . ?
C6 C7 H7 105.6 . . ?
C8 C7 H7 105.7 . . ?
C11 C7 H7 105.6 . . ?
C9 C8 C7 111.1(3) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C1 C9 C5 117.0(3) . . ?
C1 C9 C8 120.4(3) . . ?
C5 C9 C8 122.6(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O1 122.6(3) . . ?
O2 C11 C7 119.0(3) . . ?
O1 C11 C7 118.4(3) . . ?

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
F1 C1 C2 C3 -179.6(4) . . . . ?
C9 C1 C2 C3 1.9(7) . . . . ?
C1 C2 C3 C4 -2.3(7) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C6 N1 C5 C4 -169.3(3) . . . . ?
C10 N1 C5 C4 -10.2(5) . . . . ?
C6 N1 C5 C9 12.7(5) . . . . ?
C10 N1 C5 C9 171.8(3) . . . . ?
C3 C4 C5 N1 -177.1(4) . . . . ?
C3 C4 C5 C9 0.9(6) . . . . ?
C5 N1 C6 C7 -36.6(5) . . . . ?
C10 N1 C6 C7 163.5(4) . . . . ?
N1 C6 C7 C8 50.5(5) . . . . ?
N1 C6 C7 C11 -179.8(3) . . . . ?
C6 C7 C8 C9 -39.7(4) . . . . ?
C11 C7 C8 C9 -169.1(3) . . . . ?
C2 C1 C9 C5 -0.1(6) . . . . ?
F1 C1 C9 C5 -178.6(3) . . . . ?
C2 C1 C9 C8 179.5(4) . . . . ?
F1 C1 C9 C8 1.0(5) . . . . ?
N1 C5 C9 C1 176.8(3) . . . . ?
C4 C5 C9 C1 -1.3(5) . . . . ?
N1 C5 C9 C8 -2.8(5) . . . . ?
C4 C5 C9 C8 179.1(3) . . . . ?
C7 C8 C9 C1 -162.9(3) . . . . ?
C7 C8 C9 C5 16.6(5) . . . . ?
C6 C7 C11 O2 31.3(6) . . . . ?
C8 C7 C11 O2 161.8(4) . . . . ?
C6 C7 C11 O1 -151.3(4) . . . . ?
C8 C7 C11 O1 -20.8(6) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.043

