# 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_RY20180528
_database_code_depnum_ccdc_archive 'CCDC 1904675'
loop_
_audit_author_name
_audit_author_address
'fluorianted pipecolic acid intermediates'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C17H22FNO3
_chemical_formula_sum            'C17 H22 F N O3'
_chemical_formula_weight         307.35

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'

_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                   8.6569(13)
_cell_length_b                   11.7473(17)
_cell_length_c                   16.347(2)
_cell_angle_alpha                98.164(11)
_cell_angle_beta                 91.884(11)
_cell_angle_gamma                90.183(12)
_cell_volume                     1644.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3308
_cell_measurement_theta_min      3.9500
_cell_measurement_theta_max      26.4700

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   0.6587
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            12593
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.331
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6127
_reflns_number_gt                3463
_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-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1429P)²+1.2648P] 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         6127
_refine_ls_number_parameters     405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1611
_refine_ls_R_factor_gt           0.1030
_refine_ls_wR_factor_ref         0.3163
_refine_ls_wR_factor_gt          0.2644
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
F1 F 0.1588(5) 0.3081(3) 0.9252(2) 0.1021(12) Uani 1 1 d . . . . .
O1 O 0.4287(4) -0.1944(3) 0.4962(2) 0.0742(10) Uani 1 1 d . . . . .
O2 O -0.1394(4) 0.0852(3) 0.7169(2) 0.0661(9) Uani 1 1 d . . . . .
O3 O -0.0746(4) 0.0338(3) 0.84264(19) 0.0563(8) Uani 1 1 d . . . . .
N1 N 0.0954(4) 0.1311(3) 0.7793(2) 0.0492(9) Uani 1 1 d . . . . .
C1 C 0.3382(8) -0.2617(5) 0.4327(4) 0.092(2) Uani 1 1 d . . . . .
H1A H 0.2917 -0.2124 0.3969 0.138 Uiso 1 1 calc R U . . .
H1B H 0.2588 -0.3017 0.4571 0.138 Uiso 1 1 calc R U . . .
H1C H 0.4032 -0.3165 0.4012 0.138 Uiso 1 1 calc R U . . .
C2 C 0.3588(6) -0.1052(4) 0.5440(3) 0.0558(12) Uani 1 1 d . . . . .
C3 C 0.1999(6) -0.0847(4) 0.5396(3) 0.0606(13) Uani 1 1 d . . . . .
H3 H 0.1359 -0.1322 0.5026 0.073 Uiso 1 1 calc R U . . .
C4 C 0.1389(6) 0.0070(4) 0.5907(3) 0.0594(12) Uani 1 1 d . . . . .
H4 H 0.0336 0.0214 0.5865 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2299(5) 0.0778(4) 0.6478(3) 0.0500(11) Uani 1 1 d . . . . .
C6 C 0.3880(6) 0.0558(5) 0.6502(3) 0.0619(13) Uani 1 1 d . . . . .
H6 H 0.4527 0.1035 0.6867 0.074 Uiso 1 1 calc R U . . .
C7 C 0.4504(6) -0.0351(5) 0.5997(3) 0.0631(13) Uani 1 1 d . . . . .
H7 H 0.5559 -0.0490 0.6036 0.076 Uiso 1 1 calc R U . . .
C8 C 0.1547(6) 0.1740(4) 0.7059(3) 0.0541(12) Uani 1 1 d . . . . .
H8 H 0.0666 0.2024 0.6757 0.065 Uiso 1 1 calc R U . . .
C9 C 0.2072(5) 0.1276(4) 0.8474(3) 0.0505(11) Uani 1 1 d . . . . .
H9A H 0.2905 0.0761 0.8293 0.061 Uiso 1 1 calc R U . . .
H9B H 0.1575 0.0981 0.8925 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2714(7) 0.2441(4) 0.8770(3) 0.0666(14) Uani 1 1 d . . . . .
H10 H 0.3642 0.2368 0.9119 0.080 Uiso 1 1 calc R U . . .
C11 C 0.3119(6) 0.3065(4) 0.8087(4) 0.0677(14) Uani 1 1 d . . . . .
H11 H 0.3745 0.3717 0.8202 0.081 Uiso 1 1 calc R U . . .
C12 C 0.2632(6) 0.2737(4) 0.7322(3) 0.0641(14) Uani 1 1 d . . . . .
H12 H 0.2978 0.3146 0.6916 0.077 Uiso 1 1 calc R U . . .
C13 C -0.0483(5) 0.0831(4) 0.7753(3) 0.0495(11) Uani 1 1 d . . . . .
C14 C -0.2229(5) -0.0218(4) 0.8533(3) 0.0556(12) Uani 1 1 d . . . . .
C15 C -0.3519(7) 0.0675(6) 0.8605(4) 0.0900(19) Uani 1 1 d . . . . .
H15A H -0.3587 0.1027 0.8110 0.135 Uiso 1 1 calc R U . . .
H15B H -0.3294 0.1254 0.9071 0.135 Uiso 1 1 calc R U . . .
H15C H -0.4484 0.0306 0.8680 0.135 Uiso 1 1 calc R U . . .
C16 C -0.1975(7) -0.0653(6) 0.9359(3) 0.0842(18) Uani 1 1 d . . . . .
H16A H -0.1801 -0.0012 0.9787 0.126 Uiso 1 1 calc R U . . .
H16B H -0.1092 -0.1147 0.9335 0.126 Uiso 1 1 calc R U . . .
H16C H -0.2873 -0.1075 0.9478 0.126 Uiso 1 1 calc R U . . .
C17 C -0.2557(8) -0.1188(5) 0.7853(4) 0.0897(19) Uani 1 1 d . . . . .
H17A H -0.1728 -0.1731 0.7836 0.135 Uiso 1 1 calc R U . . .
H17B H -0.2645 -0.0895 0.7334 0.135 Uiso 1 1 calc R U . . .
H17C H -0.3507 -0.1560 0.7952 0.135 Uiso 1 1 calc R U . . .
F2 F 0.6023(5) 0.1926(3) 0.0696(2) 0.1013(12) Uani 1 1 d . . . . .
O4 O 0.9284(4) 0.6897(3) 0.5017(2) 0.0737(10) Uani 1 1 d . . . . .
O5 O 0.3815(4) 0.4682(3) 0.15487(18) 0.0565(8) Uani 1 1 d . . . . .
O6 O 0.3306(4) 0.4140(3) 0.2803(2) 0.0632(9) Uani 1 1 d . . . . .
N2 N 0.5576(4) 0.3684(3) 0.2176(2) 0.0500(9) Uani 1 1 d . . . . .
C18 C 0.8482(8) 0.7553(5) 0.5661(4) 0.0881(19) Uani 1 1 d . . . . .
H18A H 0.7616 0.7922 0.5430 0.132 Uiso 1 1 calc R U . . .
H18B H 0.9165 0.8126 0.5956 0.132 Uiso 1 1 calc R U . . .
H18C H 0.8121 0.7056 0.6033 0.132 Uiso 1 1 calc R U . . .
C19 C 0.8513(6) 0.6014(4) 0.4542(3) 0.0550(12) Uani 1 1 d . . . . .
C20 C 0.9357(6) 0.5308(5) 0.3976(3) 0.0633(13) Uani 1 1 d . . . . .
H20 H 1.0410 0.5445 0.3942 0.076 Uiso 1 1 calc R U . . .
C21 C 0.8673(6) 0.4414(4) 0.3466(3) 0.0615(13) Uani 1 1 d . . . . .
H21 H 0.9270 0.3948 0.3094 0.074 Uiso 1 1 calc R U . . .
C22 C 0.7089(5) 0.4187(4) 0.3494(3) 0.0491(11) Uani 1 1 d . . . . .
C23 C 0.6281(6) 0.4891(4) 0.4072(3) 0.0580(12) Uani 1 1 d . . . . .
H23 H 0.5231 0.4753 0.4116 0.070 Uiso 1 1 calc R U . . .
C24 C 0.6966(6) 0.5790(4) 0.4587(3) 0.0600(13) Uani 1 1 d . . . . .
H24 H 0.6377 0.6248 0.4968 0.072 Uiso 1 1 calc R U . . .
C25 C 0.6257(5) 0.3244(4) 0.2910(3) 0.0521(11) Uani 1 1 d . . . . .
H25 H 0.5409 0.2957 0.3209 0.062 Uiso 1 1 calc R U . . .
C26 C 0.7286(6) 0.2243(4) 0.2632(3) 0.0655(14) Uani 1 1 d . . . . .
H26 H 0.7662 0.1821 0.3035 0.079 Uiso 1 1 calc R U . . .
C27 C 0.7699(7) 0.1914(4) 0.1871(4) 0.0712(15) Uani 1 1 d . . . . .
H27 H 0.8319 0.1269 0.1757 0.085 Uiso 1 1 calc R U . . .
C28 C 0.7192(6) 0.2556(4) 0.1183(3) 0.0669(14) Uani 1 1 d . . . . .
H28 H 0.8076 0.2641 0.0837 0.080 Uiso 1 1 calc R U . . .
C29 C 0.6599(6) 0.3718(4) 0.1493(3) 0.0549(12) Uani 1 1 d . . . . .
H29A H 0.7462 0.4230 0.1674 0.066 Uiso 1 1 calc R U . . .
H29B H 0.6044 0.4020 0.1047 0.066 Uiso 1 1 calc R U . . .
C30 C 0.4128(5) 0.4170(4) 0.2219(3) 0.0496(11) Uani 1 1 d . . . . .
C33 C 0.1034(7) 0.4330(5) 0.1342(4) 0.0802(16) Uani 1 1 d . . . . .
H33A H 0.1263 0.3740 0.0894 0.120 Uiso 1 1 calc R U . . .
H33B H 0.0063 0.4675 0.1226 0.120 Uiso 1 1 calc R U . . .
H33C H 0.0975 0.3998 0.1844 0.120 Uiso 1 1 calc R U . . .
C34 C 0.2492(7) 0.5696(5) 0.0631(3) 0.0777(16) Uani 1 1 d . . . . .
H34A H 0.3352 0.6222 0.0684 0.117 Uiso 1 1 calc R U . . .
H34B H 0.1569 0.6089 0.0493 0.117 Uiso 1 1 calc R U . . .
H34C H 0.2677 0.5069 0.0202 0.117 Uiso 1 1 calc R U . . .
C35 C 0.2297(6) 0.5237(4) 0.1439(3) 0.0581(12) Uani 1 1 d . . . . .
C36 C 0.2067(8) 0.6195(5) 0.2138(4) 0.0852(18) Uani 1 1 d . . . . .
H36A H 0.1966 0.5879 0.2644 0.128 Uiso 1 1 calc R U . . .
H36B H 0.1148 0.6610 0.2027 0.128 Uiso 1 1 calc R U . . .
H36C H 0.2941 0.6709 0.2189 0.128 Uiso 1 1 calc R U . . .


_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 C10 1.423(6) . ?
O1 C2 1.370(6) . ?
O1 C1 1.423(7) . ?
O2 C13 1.221(5) . ?
O3 C13 1.340(5) . ?
O3 C14 1.465(5) . ?
N1 C13 1.361(6) . ?
N1 C9 1.457(5) . ?
N1 C8 1.472(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.369(7) . ?
C2 C3 1.398(7) . ?
C3 C4 1.383(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(7) . ?
C5 C8 1.530(6) . ?
C6 C7 1.377(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C12 1.503(7) . ?
C8 H8 0.9800 . ?
C9 C10 1.485(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.472(7) . ?
C10 H10 0.9800 . ?
C11 C12 1.311(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C17 1.493(7) . ?
C14 C16 1.521(7) . ?
C14 C15 1.531(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
F2 C28 1.408(6) . ?
O4 C19 1.363(6) . ?
O4 C18 1.416(6) . ?
O5 C30 1.343(5) . ?
O5 C35 1.486(6) . ?
O6 C30 1.214(5) . ?
N2 C30 1.379(6) . ?
N2 C29 1.452(5) . ?
N2 C25 1.479(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.370(7) . ?
C19 C20 1.381(7) . ?
C20 C21 1.365(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.399(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(6) . ?
C22 C25 1.519(6) . ?
C23 C24 1.373(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.505(7) . ?
C25 H25 0.9800 . ?
C26 C27 1.311(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.496(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.486(7) . ?
C28 H28 0.9800 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C33 C35 1.514(7) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.510(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.504(7) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 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
C2 O1 C1 118.2(4) . . ?
C13 O3 C14 121.4(3) . . ?
C13 N1 C9 124.2(3) . . ?
C13 N1 C8 119.4(4) . . ?
C9 N1 C8 115.7(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 O1 117.5(5) . . ?
C7 C2 C3 119.2(5) . . ?
O1 C2 C3 123.3(4) . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 121.9(5) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 117.3(4) . . ?
C4 C5 C8 119.6(4) . . ?
C6 C5 C8 123.1(4) . . ?
C7 C6 C5 121.4(5) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C2 C7 C6 120.7(5) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C8 C12 109.8(4) . . ?
N1 C8 C5 111.4(3) . . ?
C12 C8 C5 112.3(4) . . ?
N1 C8 H8 107.7 . . ?
C12 C8 H8 107.7 . . ?
C5 C8 H8 107.7 . . ?
N1 C9 C10 110.8(4) . . ?
N1 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
F1 C10 C11 108.9(4) . . ?
F1 C10 C9 108.4(4) . . ?
C11 C10 C9 112.5(4) . . ?
F1 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C12 C11 C10 122.5(5) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C8 124.2(4) . . ?
C11 C12 H12 117.9 . . ?
C8 C12 H12 117.9 . . ?
O2 C13 O3 125.4(4) . . ?
O2 C13 N1 123.2(4) . . ?
O3 C13 N1 111.4(4) . . ?
O3 C14 C17 111.2(4) . . ?
O3 C14 C16 102.4(4) . . ?
C17 C14 C16 111.2(4) . . ?
O3 C14 C15 110.0(4) . . ?
C17 C14 C15 112.3(5) . . ?
C16 C14 C15 109.3(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 O4 C18 118.0(4) . . ?
C30 O5 C35 120.6(3) . . ?
C30 N2 C29 124.2(4) . . ?
C30 N2 C25 119.2(3) . . ?
C29 N2 C25 116.0(4) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C24 124.4(4) . . ?
O4 C19 C20 117.2(4) . . ?
C24 C19 C20 118.4(5) . . ?
C21 C20 C19 121.2(5) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 121.1(5) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 116.5(4) . . ?
C23 C22 C25 120.3(4) . . ?
C21 C22 C25 123.2(4) . . ?
C24 C23 C22 122.5(5) . . ?
C24 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
C19 C24 C23 120.3(5) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.9 . . ?
N2 C25 C26 109.2(4) . . ?
N2 C25 C22 111.7(3) . . ?
C26 C25 C22 112.7(4) . . ?
N2 C25 H25 107.7 . . ?
C26 C25 H25 107.7 . . ?
C22 C25 H25 107.7 . . ?
C27 C26 C25 125.7(5) . . ?
C27 C26 H26 117.1 . . ?
C25 C26 H26 117.1 . . ?
C26 C27 C28 121.2(5) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
F2 C28 C29 109.0(4) . . ?
F2 C28 C27 109.4(4) . . ?
C29 C28 C27 112.3(4) . . ?
F2 C28 H28 108.7 . . ?
C29 C28 H28 108.7 . . ?
C27 C28 H28 108.7 . . ?
N2 C29 C28 111.5(4) . . ?
N2 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
N2 C29 H29B 109.3 . . ?
C28 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
O6 C30 O5 126.8(4) . . ?
O6 C30 N2 122.7(4) . . ?
O5 C30 N2 110.4(4) . . ?
C35 C33 H33A 109.5 . . ?
C35 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C35 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 H34A 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C35 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O5 C35 C36 110.1(4) . . ?
O5 C35 C34 101.6(4) . . ?
C36 C35 C34 111.4(4) . . ?
O5 C35 C33 109.2(4) . . ?
C36 C35 C33 113.9(5) . . ?
C34 C35 C33 110.0(4) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

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
C1 O1 C2 C7 -174.3(5) . . . . ?
C1 O1 C2 C3 7.2(7) . . . . ?
C7 C2 C3 C4 1.0(7) . . . . ?
O1 C2 C3 C4 179.5(4) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C3 C4 C5 C6 2.1(7) . . . . ?
C3 C4 C5 C8 -176.8(4) . . . . ?
C4 C5 C6 C7 -2.1(7) . . . . ?
C8 C5 C6 C7 176.8(4) . . . . ?
O1 C2 C7 C6 -179.6(4) . . . . ?
C3 C2 C7 C6 -1.0(7) . . . . ?
C5 C6 C7 C2 1.6(8) . . . . ?
C13 N1 C8 C12 149.5(4) . . . . ?
C9 N1 C8 C12 -39.8(5) . . . . ?
C13 N1 C8 C5 -85.4(5) . . . . ?
C9 N1 C8 C5 85.3(5) . . . . ?
C4 C5 C8 N1 84.5(5) . . . . ?
C6 C5 C8 N1 -94.3(5) . . . . ?
C4 C5 C8 C12 -151.8(4) . . . . ?
C6 C5 C8 C12 29.3(6) . . . . ?
C13 N1 C9 C10 -130.5(5) . . . . ?
C8 N1 C9 C10 59.3(5) . . . . ?
N1 C9 C10 F1 76.3(5) . . . . ?
N1 C9 C10 C11 -44.1(6) . . . . ?
F1 C10 C11 C12 -105.3(6) . . . . ?
C9 C10 C11 C12 14.9(8) . . . . ?
C10 C11 C12 C8 3.5(8) . . . . ?
N1 C8 C12 C11 8.2(7) . . . . ?
C5 C8 C12 C11 -116.3(5) . . . . ?
C14 O3 C13 O2 -1.5(7) . . . . ?
C14 O3 C13 N1 178.8(4) . . . . ?
C9 N1 C13 O2 -178.7(4) . . . . ?
C8 N1 C13 O2 -8.8(7) . . . . ?
C9 N1 C13 O3 1.0(6) . . . . ?
C8 N1 C13 O3 170.8(3) . . . . ?
C13 O3 C14 C17 60.3(5) . . . . ?
C13 O3 C14 C16 179.2(4) . . . . ?
C13 O3 C14 C15 -64.7(5) . . . . ?
C18 O4 C19 C24 7.2(7) . . . . ?
C18 O4 C19 C20 -173.2(5) . . . . ?
O4 C19 C20 C21 -179.0(4) . . . . ?
C24 C19 C20 C21 0.7(7) . . . . ?
C19 C20 C21 C22 0.5(8) . . . . ?
C20 C21 C22 C23 -1.5(7) . . . . ?
C20 C21 C22 C25 176.6(4) . . . . ?
C21 C22 C23 C24 1.4(7) . . . . ?
C25 C22 C23 C24 -176.8(4) . . . . ?
O4 C19 C24 C23 178.8(4) . . . . ?
C20 C19 C24 C23 -0.8(7) . . . . ?
C22 C23 C24 C19 -0.3(7) . . . . ?
C30 N2 C25 C26 149.0(4) . . . . ?
C29 N2 C25 C26 -39.6(5) . . . . ?
C30 N2 C25 C22 -85.7(5) . . . . ?
C29 N2 C25 C22 85.7(5) . . . . ?
C23 C22 C25 N2 84.7(5) . . . . ?
C21 C22 C25 N2 -93.4(5) . . . . ?
C23 C22 C25 C26 -152.0(4) . . . . ?
C21 C22 C25 C26 30.0(6) . . . . ?
N2 C25 C26 C27 9.2(7) . . . . ?
C22 C25 C26 C27 -115.6(6) . . . . ?
C25 C26 C27 C28 1.8(8) . . . . ?
C26 C27 C28 F2 -105.2(6) . . . . ?
C26 C27 C28 C29 15.9(7) . . . . ?
C30 N2 C29 C28 -129.9(5) . . . . ?
C25 N2 C29 C28 59.2(5) . . . . ?
F2 C28 C29 N2 77.0(5) . . . . ?
C27 C28 C29 N2 -44.3(6) . . . . ?
C35 O5 C30 O6 -3.5(7) . . . . ?
C35 O5 C30 N2 178.1(4) . . . . ?
C29 N2 C30 O6 -179.1(4) . . . . ?
C25 N2 C30 O6 -8.5(7) . . . . ?
C29 N2 C30 O5 -0.6(6) . . . . ?
C25 N2 C30 O5 170.0(3) . . . . ?
C30 O5 C35 C36 61.0(5) . . . . ?
C30 O5 C35 C34 179.0(4) . . . . ?
C30 O5 C35 C33 -64.8(5) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.073



####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1916814'
loop_
_audit_author_name
_audit_author_address
'difluorinated pipecolic acid'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C17H23F2NO3
_chemical_formula_sum            'C17 H23 F2 N O3'
_chemical_formula_weight         327.36

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.0751(5)
_cell_length_b                   6.1933(3)
_cell_length_c                   15.1581(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.790(4)
_cell_angle_gamma                90
_cell_volume                     841.95(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4471
_cell_measurement_theta_min      3.9720
_cell_measurement_theta_max      26.5570

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   0.7516
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            8892
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.266
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             3025
_reflns_number_gt                2760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.933

_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-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0490P)²+0.0236P] 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_abs_structure_details 
; 
 Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration s
_refine_ls_number_reflns         3025
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.098
_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
C1 C 0.8981(4) 0.3354(6) 0.4724(2) 0.0663(9) Uani 1 1 d . . . . .
H1A H 0.9739 0.3623 0.5227 0.099 Uiso 1 1 calc R U . . .
H1B H 0.8596 0.4703 0.4476 0.099 Uiso 1 1 calc R U . . .
H1C H 0.9402 0.2558 0.4279 0.099 Uiso 1 1 calc R U . . .
C2 C 0.6962(3) 0.3159(5) 0.55569(17) 0.0437(7) Uani 1 1 d . . . . .
C3 C 0.5738(3) 0.2018(5) 0.57365(17) 0.0476(7) Uani 1 1 d . . . . .
H3 H 0.5537 0.0653 0.5491 0.057 Uiso 1 1 calc R U . . .
C4 C 0.4813(3) 0.2905(4) 0.62812(17) 0.0426(7) Uani 1 1 d . . . . .
H4 H 0.3992 0.2121 0.6401 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5079(3) 0.4944(4) 0.66560(14) 0.0355(6) Uani 1 1 d . . . . .
C6 C 0.6303(3) 0.6034(4) 0.64664(16) 0.0417(6) Uani 1 1 d . . . . .
H6 H 0.6506 0.7399 0.6711 0.050 Uiso 1 1 calc R U . . .
C7 C 0.7255(3) 0.5173(5) 0.59205(17) 0.0465(7) Uani 1 1 d . . . . .
H7 H 0.8080 0.5952 0.5803 0.056 Uiso 1 1 calc R U . . .
C8 C 0.3975(3) 0.5922(4) 0.72134(16) 0.0377(6) Uani 1 1 d . . . . .
H8 H 0.3116 0.6450 0.6799 0.045 Uiso 1 1 calc R U . . .
C9 C 0.4589(3) 0.7825(4) 0.78056(19) 0.0423(6) Uani 1 1 d . . . . .
H9A H 0.5021 0.8881 0.7447 0.051 Uiso 1 1 calc R U . . .
H9B H 0.3779 0.8516 0.8048 0.051 Uiso 1 1 calc R U . . .
C10 C 0.5759(3) 0.7086(4) 0.85611(17) 0.0412(6) Uani 1 1 d . . . . .
H10 H 0.6601 0.6463 0.8314 0.049 Uiso 1 1 calc R U . . .
C11 C 0.5126(3) 0.5417(4) 0.91105(16) 0.0398(6) Uani 1 1 d . . . . .
H11 H 0.4338 0.6053 0.9403 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4512(3) 0.3528(4) 0.85304(15) 0.0355(6) Uani 1 1 d . . . . .
H12A H 0.5320 0.2795 0.8302 0.043 Uiso 1 1 calc R U . . .
H12B H 0.4043 0.2504 0.8884 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1987(3) 0.3621(4) 0.76126(16) 0.0375(6) Uani 1 1 d . . . . .
C14 C 0.0180(3) 0.1328(5) 0.82152(17) 0.0445(7) Uani 1 1 d . . . . .
C15 C -0.0839(4) 0.3182(7) 0.8344(3) 0.0831(12) Uani 1 1 d . . . . .
H15A H -0.0384 0.4062 0.8833 0.125 Uiso 1 1 calc R U . . .
H15B H -0.1771 0.2631 0.8473 0.125 Uiso 1 1 calc R U . . .
H15C H -0.1010 0.4035 0.7810 0.125 Uiso 1 1 calc R U . . .
C16 C 0.0389(4) -0.0130(7) 0.9019(2) 0.0772(12) Uani 1 1 d . . . . .
H16A H 0.0802 0.0682 0.9538 0.116 Uiso 1 1 calc R U . . .
H16B H 0.1056 -0.1284 0.8927 0.116 Uiso 1 1 calc R U . . .
H16C H -0.0557 -0.0720 0.9105 0.116 Uiso 1 1 calc R U . . .
C17 C -0.0350(5) 0.0072(7) 0.7376(2) 0.0823(12) Uani 1 1 d . . . . .
H17A H -0.1278 -0.0625 0.7429 0.124 Uiso 1 1 calc R U . . .
H17B H 0.0380 -0.0998 0.7290 0.124 Uiso 1 1 calc R U . . .
H17C H -0.0491 0.1037 0.6875 0.124 Uiso 1 1 calc R U . . .
F1 F 0.6258(2) 0.8869(3) 0.90981(11) 0.0617(5) Uani 1 1 d . . . . .
F2 F 0.62720(18) 0.4618(3) 0.97517(10) 0.0567(5) Uani 1 1 d . . . . .
N1 N 0.3426(2) 0.4294(3) 0.77897(13) 0.0373(5) Uani 1 1 d . . . . .
O1 O 0.7813(3) 0.2141(4) 0.50024(14) 0.0628(6) Uani 1 1 d . . . . .
O2 O 0.16971(19) 0.2124(3) 0.82006(12) 0.0480(5) Uani 1 1 d . . . . .
O3 O 0.1101(2) 0.4297(4) 0.69916(12) 0.0598(6) 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 O1 1.416(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.373(4) . ?
C2 O1 1.378(3) . ?
C2 C3 1.379(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(3) . ?
C5 C8 1.530(4) . ?
C6 C7 1.391(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.470(3) . ?
C8 C9 1.534(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.509(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 F1 1.406(3) . ?
C10 C11 1.496(4) . ?
C10 H10 0.9800 . ?
C11 F2 1.401(3) . ?
C11 C12 1.518(3) . ?
C11 H11 0.9800 . ?
C12 N1 1.456(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.215(3) . ?
C13 O2 1.340(3) . ?
C13 N1 1.358(3) . ?
C14 O2 1.466(3) . ?
C14 C15 1.505(5) . ?
C14 C16 1.505(4) . ?
C14 C17 1.506(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 O1 124.7(3) . . ?
C7 C2 C3 119.9(3) . . ?
O1 C2 C3 115.4(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 117.3(2) . . ?
C6 C5 C8 122.8(2) . . ?
C4 C5 C8 119.8(2) . . ?
C5 C6 C7 122.3(2) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C2 C7 C6 119.2(3) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
N1 C8 C5 111.5(2) . . ?
N1 C8 C9 107.76(19) . . ?
C5 C8 C9 114.7(2) . . ?
N1 C8 H8 107.5 . . ?
C5 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C10 C9 C8 111.2(2) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
F1 C10 C11 109.74(19) . . ?
F1 C10 C9 109.2(2) . . ?
C11 C10 C9 110.3(2) . . ?
F1 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C9 C10 H10 109.2 . . ?
F2 C11 C10 108.9(2) . . ?
F2 C11 C12 107.3(2) . . ?
C10 C11 C12 110.39(19) . . ?
F2 C11 H11 110.1 . . ?
C10 C11 H11 110.1 . . ?
C12 C11 H11 110.1 . . ?
N1 C12 C11 109.92(19) . . ?
N1 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
N1 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O3 C13 O2 125.5(2) . . ?
O3 C13 N1 123.4(2) . . ?
O2 C13 N1 111.2(2) . . ?
O2 C14 C15 110.0(3) . . ?
O2 C14 C16 102.2(2) . . ?
C15 C14 C16 110.9(3) . . ?
O2 C14 C17 109.9(3) . . ?
C15 C14 C17 112.4(3) . . ?
C16 C14 C17 111.0(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N1 C12 124.73(19) . . ?
C13 N1 C8 119.8(2) . . ?
C12 N1 C8 115.52(19) . . ?
C2 O1 C1 117.0(2) . . ?
C13 O2 C14 121.5(2) . . ?

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
C7 C2 C3 C4 0.0(4) . . . . ?
O1 C2 C3 C4 -179.7(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3 C4 C5 C8 176.5(2) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C8 C5 C6 C7 -176.6(2) . . . . ?
O1 C2 C7 C6 179.5(3) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C5 C6 C7 C2 0.0(4) . . . . ?
C6 C5 C8 N1 -143.0(2) . . . . ?
C4 C5 C8 N1 40.2(3) . . . . ?
C6 C5 C8 C9 -20.2(3) . . . . ?
C4 C5 C8 C9 163.1(2) . . . . ?
N1 C8 C9 C10 55.2(3) . . . . ?
C5 C8 C9 C10 -69.6(3) . . . . ?
C8 C9 C10 F1 -178.4(2) . . . . ?
C8 C9 C10 C11 -57.8(3) . . . . ?
F1 C10 C11 F2 -65.2(3) . . . . ?
C9 C10 C11 F2 174.4(2) . . . . ?
F1 C10 C11 C12 177.2(2) . . . . ?
C9 C10 C11 C12 56.9(3) . . . . ?
F2 C11 C12 N1 -173.82(19) . . . . ?
C10 C11 C12 N1 -55.3(3) . . . . ?
O3 C13 N1 C12 179.6(3) . . . . ?
O2 C13 N1 C12 -1.1(3) . . . . ?
O3 C13 N1 C8 0.0(4) . . . . ?
O2 C13 N1 C8 179.3(2) . . . . ?
C11 C12 N1 C13 -122.4(3) . . . . ?
C11 C12 N1 C8 57.2(3) . . . . ?
C5 C8 N1 C13 -110.1(3) . . . . ?
C9 C8 N1 C13 123.2(2) . . . . ?
C5 C8 N1 C12 70.2(3) . . . . ?
C9 C8 N1 C12 -56.5(3) . . . . ?
C7 C2 O1 C1 -6.4(4) . . . . ?
C3 C2 O1 C1 173.2(3) . . . . ?
O3 C13 O2 C14 -8.0(4) . . . . ?
N1 C13 O2 C14 172.8(2) . . . . ?
C15 C14 O2 C13 -57.2(3) . . . . ?
C16 C14 O2 C13 -175.1(3) . . . . ?
C17 C14 O2 C13 67.1(3) . . . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_A_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1916815'
loop_
_audit_author_name
_audit_author_address
'difluorianted pipecolic acid'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C17H23F2NO3
_chemical_formula_sum            'C17 H23 F2 N O3'
_chemical_formula_weight         327.36

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      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                   6.0625(4)
_cell_length_b                   22.0365(15)
_cell_length_c                   12.8581(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.522(7)
_cell_angle_gamma                90
_cell_volume                     1717.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4471
_cell_measurement_theta_min      3.9720
_cell_measurement_theta_max      26.5570

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   0.6557
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            11473
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.361
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3173
_reflns_number_gt                2417
_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-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0527P)²+0.4319P] 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         3173
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C -0.4346(5) 0.04329(13) 0.3701(2) 0.0983(9) Uani 1 1 d . . . . .
H1A H -0.3825 0.0516 0.3013 0.147 Uiso 1 1 calc R U . . .
H1B H -0.5444 0.0727 0.3885 0.147 Uiso 1 1 calc R U . . .
H1C H -0.4980 0.0034 0.3720 0.147 Uiso 1 1 calc R U . . .
C2 C -0.1337(4) 0.09884(9) 0.44525(17) 0.0656(6) Uani 1 1 d . . . . .
C3 C 0.0516(5) 0.09846(10) 0.5088(2) 0.0923(9) Uani 1 1 d . . . . .
H3 H 0.0880 0.0635 0.5456 0.111 Uiso 1 1 calc R U . . .
C4 C 0.1826(4) 0.14907(10) 0.51847(19) 0.0807(8) Uani 1 1 d . . . . .
H4 H 0.3054 0.1477 0.5623 0.097 Uiso 1 1 calc R U . . .
C5 C 0.1362(3) 0.20199(8) 0.46461(14) 0.0499(5) Uani 1 1 d . . . . .
C6 C -0.0492(3) 0.20091(9) 0.40108(15) 0.0560(5) Uani 1 1 d . . . . .
H6 H -0.0856 0.2356 0.3636 0.067 Uiso 1 1 calc R U . . .
C7 C -0.1823(3) 0.15036(9) 0.39104(16) 0.0612(5) Uani 1 1 d . . . . .
H7 H -0.3053 0.1515 0.3473 0.073 Uiso 1 1 calc R U . . .
C8 C 0.2809(3) 0.25855(8) 0.46687(14) 0.0508(5) Uani 1 1 d . . . . .
H8 H 0.3475 0.2620 0.3979 0.061 Uiso 1 1 calc R U . . .
C9 C 0.4719(3) 0.25853(10) 0.54633(16) 0.0590(5) Uani 1 1 d . . . . .
H9A H 0.5496 0.2201 0.5426 0.071 Uiso 1 1 calc R U . . .
H9B H 0.5751 0.2905 0.5290 0.071 Uiso 1 1 calc R U . . .
C10 C 0.3904(3) 0.26797(10) 0.65487(15) 0.0588(5) Uani 1 1 d . . . . .
H10 H 0.2969 0.2336 0.6741 0.071 Uiso 1 1 calc R U . . .
C11 C 0.2593(4) 0.32519(10) 0.66366(16) 0.0610(5) Uani 1 1 d . . . . .
H11 H 0.2028 0.3290 0.7345 0.073 Uiso 1 1 calc R U . . .
C12 C 0.0679(3) 0.32399(10) 0.58708(15) 0.0567(5) Uani 1 1 d . . . . .
H12A H -0.0340 0.2920 0.6060 0.068 Uiso 1 1 calc R U . . .
H12B H -0.0104 0.3623 0.5896 0.068 Uiso 1 1 calc R U . . .
C13 C 0.0848(3) 0.34654(9) 0.39824(16) 0.0542(5) Uani 1 1 d . . . . .
C14 C -0.1689(4) 0.42745(10) 0.34410(19) 0.0737(7) Uani 1 1 d . . . . .
C15 C -0.0007(5) 0.46755(12) 0.2924(2) 0.0981(9) Uani 1 1 d . . . . .
H15A H 0.1002 0.4429 0.2538 0.147 Uiso 1 1 calc R U . . .
H15B H 0.0791 0.4900 0.3445 0.147 Uiso 1 1 calc R U . . .
H15C H -0.0744 0.4952 0.2461 0.147 Uiso 1 1 calc R U . . .
C16 C -0.3267(5) 0.46472(14) 0.4096(3) 0.1155(11) Uani 1 1 d . . . . .
H16A H -0.2445 0.4875 0.4604 0.173 Uiso 1 1 calc R U . . .
H16B H -0.4277 0.4381 0.4442 0.173 Uiso 1 1 calc R U . . .
H16C H -0.4077 0.4921 0.3654 0.173 Uiso 1 1 calc R U . . .
C17 C -0.2928(4) 0.38729(12) 0.2683(2) 0.0961(9) Uani 1 1 d . . . . .
H17A H -0.3873 0.3603 0.3059 0.144 Uiso 1 1 calc R U . . .
H17B H -0.1895 0.3641 0.2284 0.144 Uiso 1 1 calc R U . . .
H17C H -0.3803 0.4120 0.2223 0.144 Uiso 1 1 calc R U . . .
F1 F 0.5730(2) 0.27031(6) 0.72318(10) 0.0829(4) Uani 1 1 d . . . . .
F2 F 0.3953(2) 0.37489(6) 0.64152(11) 0.0838(4) Uani 1 1 d . . . . .
N1 N 0.1481(2) 0.31353(7) 0.48204(11) 0.0503(4) Uani 1 1 d . . . . .
O1 O -0.2556(3) 0.04651(7) 0.44190(14) 0.0940(6) Uani 1 1 d . . . . .
O2 O -0.0577(2) 0.39005(7) 0.42421(12) 0.0710(4) Uani 1 1 d . . . . .
O3 O 0.1493(2) 0.33681(7) 0.31057(11) 0.0688(4) 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 O1 1.420(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.363(3) . ?
C2 O1 1.370(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 C8 1.524(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.469(2) . ?
C8 C9 1.537(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.499(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 F1 1.408(2) . ?
C10 C11 1.495(3) . ?
C10 H10 0.9800 . ?
C11 F2 1.401(2) . ?
C11 C12 1.515(3) . ?
C11 H11 0.9800 . ?
C12 N1 1.458(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.216(2) . ?
C13 O2 1.335(2) . ?
C13 N1 1.353(2) . ?
C14 O2 1.477(2) . ?
C14 C15 1.508(3) . ?
C14 C17 1.512(3) . ?
C14 C16 1.521(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 O1 124.8(2) . . ?
C7 C2 C3 118.6(2) . . ?
O1 C2 C3 116.6(2) . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 116.18(19) . . ?
C6 C5 C8 119.31(16) . . ?
C4 C5 C8 124.42(17) . . ?
C7 C6 C5 122.69(18) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C2 C7 C6 120.03(19) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N1 C8 C5 111.16(14) . . ?
N1 C8 C9 108.80(15) . . ?
C5 C8 C9 116.25(15) . . ?
N1 C8 H8 106.7 . . ?
C5 C8 H8 106.7 . . ?
C9 C8 H8 106.7 . . ?
C10 C9 C8 111.50(15) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
F1 C10 C9 108.81(16) . . ?
F1 C10 C11 109.72(16) . . ?
C9 C10 C11 111.54(17) . . ?
F1 C10 H10 108.9 . . ?
C9 C10 H10 108.9 . . ?
C11 C10 H10 108.9 . . ?
F2 C11 C10 109.25(17) . . ?
F2 C11 C12 109.27(16) . . ?
C10 C11 C12 109.91(16) . . ?
F2 C11 H11 109.5 . . ?
C10 C11 H11 109.5 . . ?
C12 C11 H11 109.5 . . ?
N1 C12 C11 110.17(15) . . ?
N1 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
N1 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O3 C13 O2 124.96(18) . . ?
O3 C13 N1 123.53(18) . . ?
O2 C13 N1 111.51(17) . . ?
O2 C14 C15 109.18(19) . . ?
O2 C14 C17 110.13(19) . . ?
C15 C14 C17 113.1(2) . . ?
O2 C14 C16 101.6(2) . . ?
C15 C14 C16 111.0(2) . . ?
C17 C14 C16 111.2(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N1 C12 123.93(16) . . ?
C13 N1 C8 119.32(15) . . ?
C12 N1 C8 116.19(15) . . ?
C2 O1 C1 118.12(19) . . ?
C13 O2 C14 121.22(17) . . ?

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
C7 C2 C3 C4 0.9(4) . . . . ?
O1 C2 C3 C4 -179.1(2) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 C8 -176.4(2) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C8 C5 C6 C7 176.81(18) . . . . ?
O1 C2 C7 C6 179.3(2) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C6 C5 C8 N1 49.6(2) . . . . ?
C4 C5 C8 N1 -133.9(2) . . . . ?
C6 C5 C8 C9 174.75(17) . . . . ?
C4 C5 C8 C9 -8.8(3) . . . . ?
N1 C8 C9 C10 52.0(2) . . . . ?
C5 C8 C9 C10 -74.3(2) . . . . ?
C8 C9 C10 F1 -177.32(16) . . . . ?
C8 C9 C10 C11 -56.1(2) . . . . ?
F1 C10 C11 F2 57.8(2) . . . . ?
C9 C10 C11 F2 -62.8(2) . . . . ?
F1 C10 C11 C12 177.68(15) . . . . ?
C9 C10 C11 C12 57.0(2) . . . . ?
F2 C11 C12 N1 64.6(2) . . . . ?
C10 C11 C12 N1 -55.3(2) . . . . ?
O3 C13 N1 C12 -178.58(19) . . . . ?
O2 C13 N1 C12 0.7(3) . . . . ?
O3 C13 N1 C8 -7.5(3) . . . . ?
O2 C13 N1 C8 171.80(16) . . . . ?
C11 C12 N1 C13 -132.48(19) . . . . ?
C11 C12 N1 C8 56.2(2) . . . . ?
C5 C8 N1 C13 -96.25(19) . . . . ?
C9 C8 N1 C13 134.50(17) . . . . ?
C5 C8 N1 C12 75.52(19) . . . . ?
C9 C8 N1 C12 -53.7(2) . . . . ?
C7 C2 O1 C1 5.9(4) . . . . ?
C3 C2 O1 C1 -174.1(2) . . . . ?
O3 C13 O2 C14 6.2(3) . . . . ?
N1 C13 O2 C14 -173.11(18) . . . . ?
C15 C14 O2 C13 -68.1(3) . . . . ?
C17 C14 O2 C13 56.7(3) . . . . ?
C16 C14 O2 C13 174.6(2) . . . . ?

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
C17 H17B O3 0.96 2.38 2.948(3) 117.5 .
C15 H15A O3 0.96 2.47 3.030(3) 117.3 .
C10 H10 O3 0.98 2.51 3.396(3) 149.8 4_566
C7 H7 F1 0.93 2.46 3.139(2) 130.2 4_465
C3 H3 O1 0.93 2.63 3.482(3) 152.2 3_556

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.032



