# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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-H
_database_code_depnum_ccdc_archive 'CCDC 1911910'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C5 H14 N'
_chemical_formula_sum            'C13 H15 F4 N O4'
_chemical_formula_weight         325.26

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                   8.5321(10)
_cell_length_b                   9.2554(10)
_cell_length_c                   9.7500(8)
_cell_angle_alpha                104.633(8)
_cell_angle_beta                 91.429(8)
_cell_angle_gamma                102.163(9)
_cell_volume                     725.75(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9756
_cell_measurement_theta_min      2.166
_cell_measurement_theta_max      29.476

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9756
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.166
_diffrn_reflns_theta_max         29.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4036
_reflns_number_gt                2441
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0898P)²+0.2905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3469
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1867
_refine_ls_wR_factor_gt          0.1651
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.1289(3) 0.2550(2) -0.0451(2) 0.0342(5) Uani 1 1 d . . . . .
C2 C 0.0873(2) 0.2486(2) 0.1046(2) 0.0311(4) Uani 1 1 d . . . . .
C3 C -0.0139(3) 0.3313(3) 0.1795(2) 0.0358(5) Uani 1 1 d . . . . .
C4 C -0.0453(3) 0.3280(2) 0.3169(2) 0.0342(5) Uani 1 1 d . . . . .
C5 C 0.0247(2) 0.2408(2) 0.3874(2) 0.0315(4) Uani 1 1 d . . . . .
C6 C -0.0199(3) 0.2330(3) 0.5346(2) 0.0368(5) Uani 1 1 d . . . . .
C7 C 0.1274(3) 0.1587(3) 0.3117(2) 0.0336(5) Uani 1 1 d . . . . .
C8 C 0.1569(3) 0.1619(3) 0.1743(2) 0.0346(5) Uani 1 1 d . . . . .
C9 C 0.4876(5) 0.5173(5) 0.7239(5) 0.0911(12) Uani 1 1 d . . . . .
H9A H 0.3813 0.5093 0.7558 0.137 Uiso 1 1 calc R U . . .
H9B H 0.4994 0.5759 0.6548 0.137 Uiso 1 1 calc R U . . .
H9C H 0.5656 0.5674 0.8034 0.137 Uiso 1 1 calc R U . . .
C10 C 0.5122(5) 0.3665(5) 0.6603(4) 0.0890(12) Uani 1 1 d . . . . .
H10A H 0.6189 0.3760 0.6266 0.107 Uiso 1 1 calc R U . . .
H10B H 0.4350 0.3182 0.5784 0.107 Uiso 1 1 calc R U . . .
C11 C 0.6324(4) 0.2958(4) 0.8660(3) 0.0724(9) Uani 1 1 d . . . . .
H11A H 0.6069 0.2349 0.9322 0.109 Uiso 1 1 calc R U . . .
H11B H 0.6557 0.4025 0.9161 0.109 Uiso 1 1 calc R U . . .
H11C H 0.7244 0.2719 0.8184 0.109 Uiso 1 1 calc R U . . .
C12 C 0.4602(4) 0.1031(4) 0.6738(3) 0.0686(9) Uani 1 1 d . . . . .
H12A H 0.5573 0.0813 0.6319 0.082 Uiso 1 1 calc R U . . .
H12B H 0.3803 0.0913 0.5969 0.082 Uiso 1 1 calc R U . . .
C13 C 0.3991(5) -0.0117(4) 0.7565(5) 0.0866(11) Uani 1 1 d . . . . .
H13A H 0.4803 -0.0052 0.8291 0.130 Uiso 1 1 calc R U . . .
H13B H 0.3744 -0.1130 0.6933 0.130 Uiso 1 1 calc R U . . .
H13C H 0.3039 0.0101 0.7996 0.130 Uiso 1 1 calc R U . . .
F1 F -0.0834(2) 0.42070(19) 0.11967(15) 0.0590(5) Uani 1 1 d . . . . .
F2 F -0.14287(19) 0.41458(18) 0.38279(14) 0.0537(4) Uani 1 1 d . . . . .
F3 F 0.20080(18) 0.07109(18) 0.37001(14) 0.0509(4) Uani 1 1 d . . . . .
F4 F 0.25729(19) 0.07934(19) 0.10697(15) 0.0550(4) Uani 1 1 d . . . . .
H1 H 0.059(5) 0.215(4) 0.706(4) 0.101(12) Uiso 1 1 d . . . . .
H1A H 0.409(4) 0.282(3) 0.813(3) 0.057(8) Uiso 1 1 d . . . . .
N1 N 0.4953(3) 0.2627(3) 0.7613(2) 0.0507(6) Uani 1 1 d . . . . .
O1 O 0.0964(2) 0.2168(2) 0.61408(17) 0.0492(5) Uani 1 1 d . . . . .
O2 O -0.1519(2) 0.2408(3) 0.56967(19) 0.0611(6) Uani 1 1 d . . . . .
O3 O 0.0192(2) 0.1947(2) -0.14135(16) 0.0543(5) Uani 1 1 d . . . . .
O4 O 0.26841(19) 0.3200(2) -0.05519(16) 0.0467(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 O4 1.234(3) . ?
C1 O3 1.241(3) . ?
C1 C2 1.523(3) . ?
C2 C3 1.376(3) . ?
C2 C8 1.383(3) . ?
C3 F1 1.345(2) . ?
C3 C4 1.378(3) . ?
C4 F2 1.341(2) . ?
C4 C5 1.394(3) . ?
C5 C7 1.386(3) . ?
C5 C6 1.509(3) . ?
C6 O2 1.196(3) . ?
C6 O1 1.300(3) . ?
C7 F3 1.342(2) . ?
C7 C8 1.376(3) . ?
C8 F4 1.341(2) . ?
C9 C10 1.438(6) . ?
C10 N1 1.530(4) . ?
C11 N1 1.461(4) . ?
C12 N1 1.471(4) . ?
C12 C13 1.506(5) . ?

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
O4 C1 O3 128.09(18) . . ?
O4 C1 C2 115.52(18) . . ?
O3 C1 C2 116.39(18) . . ?
C3 C2 C8 116.58(17) . . ?
C3 C2 C1 122.97(18) . . ?
C8 C2 C1 120.40(18) . . ?
F1 C3 C2 119.92(17) . . ?
F1 C3 C4 118.13(19) . . ?
C2 C3 C4 121.94(19) . . ?
F2 C4 C3 117.89(18) . . ?
F2 C4 C5 120.47(17) . . ?
C3 C4 C5 121.63(19) . . ?
C7 C5 C4 116.12(17) . . ?
C7 C5 C6 123.79(18) . . ?
C4 C5 C6 120.00(18) . . ?
O2 C6 O1 125.42(19) . . ?
O2 C6 C5 120.90(19) . . ?
O1 C6 C5 113.68(18) . . ?
F3 C7 C8 117.44(19) . . ?
F3 C7 C5 120.79(17) . . ?
C8 C7 C5 121.76(18) . . ?
F4 C8 C7 118.68(18) . . ?
F4 C8 C2 119.36(17) . . ?
C7 C8 C2 121.97(19) . . ?
C9 C10 N1 113.9(3) . . ?
N1 C12 C13 113.3(2) . . ?
C11 N1 C12 112.2(2) . . ?
C11 N1 C10 114.7(3) . . ?
C12 N1 C10 107.6(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
O4 C1 C2 C3 110.0(2) . . . . ?
O3 C1 C2 C3 -69.9(3) . . . . ?
O4 C1 C2 C8 -67.3(3) . . . . ?
O3 C1 C2 C8 112.8(2) . . . . ?
C8 C2 C3 F1 178.6(2) . . . . ?
C1 C2 C3 F1 1.2(3) . . . . ?
C8 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 -177.6(2) . . . . ?
F1 C3 C4 F2 -0.2(3) . . . . ?
C2 C3 C4 F2 178.67(19) . . . . ?
F1 C3 C4 C5 -178.6(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
F2 C4 C5 C7 -178.17(19) . . . . ?
C3 C4 C5 C7 0.2(3) . . . . ?
F2 C4 C5 C6 5.1(3) . . . . ?
C3 C4 C5 C6 -176.5(2) . . . . ?
C7 C5 C6 O2 -144.6(2) . . . . ?
C4 C5 C6 O2 31.9(3) . . . . ?
C7 C5 C6 O1 35.1(3) . . . . ?
C4 C5 C6 O1 -148.5(2) . . . . ?
C4 C5 C7 F3 -179.95(19) . . . . ?
C6 C5 C7 F3 -3.4(3) . . . . ?
C4 C5 C7 C8 -0.7(3) . . . . ?
C6 C5 C7 C8 175.9(2) . . . . ?
F3 C7 C8 F4 -0.5(3) . . . . ?
C5 C7 C8 F4 -179.80(19) . . . . ?
F3 C7 C8 C2 -180.0(2) . . . . ?
C5 C7 C8 C2 0.8(3) . . . . ?
C3 C2 C8 F4 -179.71(19) . . . . ?
C1 C2 C8 F4 -2.3(3) . . . . ?
C3 C2 C8 C7 -0.3(3) . . . . ?
C1 C2 C8 C7 177.2(2) . . . . ?
C13 C12 N1 C11 67.6(3) . . . . ?
C13 C12 N1 C10 -165.3(3) . . . . ?
C9 C10 N1 C11 -76.1(4) . . . . ?
C9 C10 N1 C12 158.3(3) . . . . ?

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
O1 H1 O3 0.96(4) 1.59(4) 2.536(2) 170(4) 1_556
N1 H1A O4 0.93(3) 1.80(3) 2.712(3) 168(3) 1_556
C13 H13A F4 0.96 2.58 3.429(4) 147.3 2_656
C12 H12B F3 0.97 2.60 3.566(3) 171.8 .
C11 H11C O2 0.96 2.64 3.451(4) 142.3 1_655
C11 H11B O4 0.96 2.52 3.479(4) 176.6 2_666
C10 H10A O2 0.97 2.54 3.371(4) 144.1 1_655
C9 H9C O4 0.96 2.65 3.595(5) 167.5 2_666

_refine_diff_density_max         0.863
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_6-D
_database_code_depnum_ccdc_archive 'CCDC 1911921'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C6 H7 D N'
_chemical_formula_sum            'C14 H7 D2 F4 N O4'
_chemical_formula_weight         333.23

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                   9.6660(7)
_cell_length_b                   10.5577(8)
_cell_length_c                   13.3682(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.575(7)
_cell_angle_gamma                90
_cell_volume                     1352.33(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6902
_cell_measurement_theta_min      2.125
_cell_measurement_theta_max      29.505

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             672.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6902
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.125
_diffrn_reflns_theta_max         29.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3778
_reflns_number_gt                2109
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0674P)²+0.0787P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3193
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.38152(19) 0.9410(2) 0.10782(15) 0.0343(5) Uani 1 1 d . . . . .
C2 C 0.22955(17) 0.95549(18) 0.12058(14) 0.0301(4) Uani 1 1 d . . . . .
C3 C 0.15452(19) 0.85175(19) 0.14723(15) 0.0344(5) Uani 1 1 d . . . . .
C4 C 0.01706(18) 0.86177(19) 0.16353(15) 0.0353(5) Uani 1 1 d . . . . .
C5 C -0.05474(18) 0.97522(19) 0.15269(14) 0.0328(5) Uani 1 1 d . . . . .
C6 C -0.20381(19) 0.9856(2) 0.17674(16) 0.0391(5) Uani 1 1 d . . . . .
C7 C 0.01854(18) 1.07724(18) 0.12245(15) 0.0337(4) Uani 1 1 d . . . . .
C8 C 0.15667(18) 1.06821(19) 0.10724(15) 0.0332(5) Uani 1 1 d . . . . .
C9 C 0.5081(2) 0.5667(2) 0.14611(17) 0.0459(6) Uani 1 1 d . . . . .
H9 H 0.4574 0.6374 0.1611 0.055 Uiso 1 1 calc R U . . .
C10 C 0.6321(2) 0.5818(2) 0.10914(17) 0.0463(5) Uani 1 1 d . . . . .
H10 H 0.6656 0.6627 0.0989 0.056 Uiso 1 1 calc R U . . .
C11 C 0.7082(2) 0.4765(2) 0.08681(16) 0.0423(5) Uani 1 1 d . . . . .
C12 C 0.6535(2) 0.3583(2) 0.10254(17) 0.0451(5) Uani 1 1 d . . . . .
H12 H 0.7018 0.2858 0.0880 0.054 Uiso 1 1 calc R U . . .
C13 C 0.5284(2) 0.3477(2) 0.13947(17) 0.0447(5) Uani 1 1 d . . . . .
H13 H 0.4916 0.2680 0.1496 0.054 Uiso 1 1 calc R U . . .
C14 C 0.8445(3) 0.4902(3) 0.0457(2) 0.0658(7) Uani 1 1 d . . . . .
H14A H 0.9200 0.4733 0.0982 0.099 Uiso 1 1 calc R U . . .
H14B H 0.8530 0.5750 0.0212 0.099 Uiso 1 1 calc R U . . .
H14C H 0.8479 0.4313 -0.0086 0.099 Uiso 1 1 calc R U . . .
F1 F 0.21321(12) 0.73722(11) 0.16151(12) 0.0586(4) Uani 1 1 d . . . . .
F2 F -0.04839(13) 0.75648(12) 0.18776(12) 0.0589(4) Uani 1 1 d . . . . .
F3 F 0.21665(11) 1.17395(11) 0.07731(11) 0.0550(4) Uani 1 1 d . . . . .
F4 F -0.04459(11) 1.19031(12) 0.10645(11) 0.0534(4) Uani 1 1 d . . . . .
D1 D 0.378(3) 0.444(2) 0.1955(19) 0.073(8) Uiso 1 1 d . . . . .
N1 N 0.45942(18) 0.45106(18) 0.16082(13) 0.0422(5) Uani 1 1 d . . . . .
O1 O 0.43337(14) 0.84026(15) 0.09476(14) 0.0550(5) Uani 1 1 d . . . . .
O2 O 0.44996(14) 1.04811(14) 0.11679(12) 0.0448(4) Uani 1 1 d . . . . .
O3 O -0.22394(16) 0.94500(18) 0.26004(12) 0.0611(5) Uani 1 1 d . . . . .
O4 O -0.28887(14) 1.03504(16) 0.11017(13) 0.0556(5) Uani 1 1 d . . . . .
D2 D 0.545(4) 1.031(3) 0.111(2) 0.103(11) 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
C1 O1 1.198(2) . ?
C1 O2 1.308(2) . ?
C1 C2 1.509(2) . ?
C2 C8 1.383(3) . ?
C2 C3 1.386(3) . ?
C3 F1 1.339(2) . ?
C3 C4 1.379(2) . ?
C4 F2 1.340(2) . ?
C4 C5 1.382(3) . ?
C5 C7 1.379(3) . ?
C5 C6 1.521(2) . ?
C6 O3 1.232(2) . ?
C6 O4 1.244(3) . ?
C7 F4 1.345(2) . ?
C7 C8 1.380(2) . ?
C8 F3 1.343(2) . ?
C9 N1 1.332(3) . ?
C9 C10 1.365(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.383(3) . ?
C11 C14 1.500(3) . ?
C12 C13 1.370(3) . ?
C13 N1 1.329(3) . ?

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 O2 124.38(17) . . ?
O1 C1 C2 122.61(18) . . ?
O2 C1 C2 112.96(16) . . ?
C8 C2 C3 116.01(16) . . ?
C8 C2 C1 124.06(16) . . ?
C3 C2 C1 119.94(16) . . ?
F1 C3 C4 116.48(17) . . ?
F1 C3 C2 121.62(16) . . ?
C4 C3 C2 121.87(17) . . ?
F2 C4 C3 118.05(17) . . ?
F2 C4 C5 119.85(15) . . ?
C3 C4 C5 122.07(17) . . ?
C7 C5 C4 115.94(16) . . ?
C7 C5 C6 122.92(17) . . ?
C4 C5 C6 121.10(17) . . ?
O3 C6 O4 128.61(18) . . ?
O3 C6 C5 115.66(18) . . ?
O4 C6 C5 115.73(18) . . ?
F4 C7 C5 120.02(15) . . ?
F4 C7 C8 117.73(16) . . ?
C5 C7 C8 122.25(17) . . ?
F3 C8 C7 116.78(16) . . ?
F3 C8 C2 121.42(15) . . ?
C7 C8 C2 121.79(17) . . ?
N1 C9 C10 120.34(19) . . ?
C9 C10 C11 120.0(2) . . ?
C12 C11 C10 117.80(19) . . ?
C12 C11 C14 121.0(2) . . ?
C10 C11 C14 121.2(2) . . ?
C13 C12 C11 120.1(2) . . ?
N1 C13 C12 120.1(2) . . ?
C13 N1 C9 121.56(18) . . ?

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
O1 C1 C2 C8 -160.9(2) . . . . ?
O2 C1 C2 C8 21.8(3) . . . . ?
O1 C1 C2 C3 19.1(3) . . . . ?
O2 C1 C2 C3 -158.18(18) . . . . ?
C8 C2 C3 F1 179.48(18) . . . . ?
C1 C2 C3 F1 -0.5(3) . . . . ?
C8 C2 C3 C4 -2.6(3) . . . . ?
C1 C2 C3 C4 177.42(18) . . . . ?
F1 C3 C4 F2 -2.9(3) . . . . ?
C2 C3 C4 F2 179.13(17) . . . . ?
F1 C3 C4 C5 179.10(18) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
F2 C4 C5 C7 -176.67(17) . . . . ?
C3 C4 C5 C7 1.3(3) . . . . ?
F2 C4 C5 C6 5.4(3) . . . . ?
C3 C4 C5 C6 -176.56(18) . . . . ?
C7 C5 C6 O3 -126.5(2) . . . . ?
C4 C5 C6 O3 51.3(3) . . . . ?
C7 C5 C6 O4 52.8(3) . . . . ?
C4 C5 C6 O4 -129.4(2) . . . . ?
C4 C5 C7 F4 177.61(18) . . . . ?
C6 C5 C7 F4 -4.5(3) . . . . ?
C4 C5 C7 C8 -2.2(3) . . . . ?
C6 C5 C7 C8 175.68(19) . . . . ?
F4 C7 C8 F3 -0.1(3) . . . . ?
C5 C7 C8 F3 179.66(17) . . . . ?
F4 C7 C8 C2 -179.16(18) . . . . ?
C5 C7 C8 C2 0.6(3) . . . . ?
C3 C2 C8 F3 -177.21(17) . . . . ?
C1 C2 C8 F3 2.8(3) . . . . ?
C3 C2 C8 C7 1.8(3) . . . . ?
C1 C2 C8 C7 -178.25(18) . . . . ?
N1 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C9 C10 C11 C14 179.7(2) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C14 C11 C12 C13 -179.5(2) . . . . ?
C11 C12 C13 N1 -0.4(3) . . . . ?
C12 C13 N1 C9 0.8(3) . . . . ?
C10 C9 N1 C13 -0.6(3) . . . . ?

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
O2 D2 O4 0.95(3) 1.60(3) 2.5414(18) 167(3) 1_655
N1 D1 O3 0.97(3) 1.67(3) 2.634(2) 171(2) 2_545
C13 H13 O2 0.93 2.39 3.258(3) 155.7 1_545
C12 H12 F4 0.93 2.63 3.409(2) 141.5 1_645
C9 H9 O1 0.93 2.32 3.034(3) 133.5 .
C9 H9 F1 0.93 2.59 3.401(2) 146.7 .

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_5-D
_database_code_depnum_ccdc_archive 'CCDC 1911919'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C6 H7 D N'
_chemical_formula_sum            'C14 H7 D2 F4 N O4'
_chemical_formula_weight         333.23

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.2862(8)
_cell_length_b                   9.7081(7)
_cell_length_c                   19.2903(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1364.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5425
_cell_measurement_theta_min      2.111
_cell_measurement_theta_max      29.487

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             672.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5425
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         29.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3798
_reflns_number_gt                2421
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_max     0.710
_reflns_Friedel_fraction_full    0.908

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0386P)²+0.1610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3069
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.2523(4) 0.7913(3) -0.03262(14) 0.0325(6) Uani 1 1 d . . . . .
C2 C 0.2774(4) 0.6412(2) -0.01546(14) 0.0290(6) Uani 1 1 d . . . . .
C3 C 0.2369(4) 0.5865(3) 0.04872(14) 0.0324(6) Uani 1 1 d . . . . .
C4 C 0.2621(4) 0.4496(3) 0.06354(13) 0.0312(6) Uani 1 1 d . . . . .
C5 C 0.3301(4) 0.3585(2) 0.01521(14) 0.0303(6) Uani 1 1 d . . . . .
C6 C 0.3570(4) 0.2055(3) 0.03122(14) 0.0316(6) Uani 1 1 d . . . . .
C7 C 0.3703(4) 0.4124(3) -0.04897(13) 0.0317(6) Uani 1 1 d . . . . .
C8 C 0.3444(4) 0.5493(3) -0.06445(14) 0.0324(6) Uani 1 1 d . . . . .
C9 C 0.5250(7) 0.2870(4) 0.2413(3) 0.0764(13) Uani 1 1 d . . . . .
H9 H 0.4322 0.2213 0.2407 0.092 Uiso 1 1 calc R U . . .
C10 C 0.5760(6) 0.3470(4) 0.3022(2) 0.0671(11) Uani 1 1 d . . . . .
H10 H 0.5200 0.3218 0.3436 0.080 Uiso 1 1 calc R U . . .
C11 C 0.7108(5) 0.4447(3) 0.30134(16) 0.0465(8) Uani 1 1 d . . . . .
H11 H 0.7457 0.4865 0.3427 0.056 Uiso 1 1 calc R U . . .
C12 C 0.7960(5) 0.4827(3) 0.24064(14) 0.0397(7) Uani 1 1 d . . . . .
C13 C 0.7408(5) 0.4174(3) 0.18090(16) 0.0484(8) Uani 1 1 d . . . . .
H13 H 0.7964 0.4395 0.1389 0.058 Uiso 1 1 calc R U . . .
C14 C 0.9410(6) 0.5917(4) 0.23837(18) 0.0645(11) Uani 1 1 d . . . . .
H14A H 0.9312 0.6490 0.2788 0.097 Uiso 1 1 calc R U . . .
H14B H 0.9249 0.6470 0.1976 0.097 Uiso 1 1 calc R U . . .
H14C H 1.0599 0.5492 0.2373 0.097 Uiso 1 1 calc R U . . .
F1 F 0.1646(3) 0.66783(16) 0.09817(9) 0.0516(5) Uani 1 1 d . . . . .
F2 F 0.2142(3) 0.40448(16) 0.12736(8) 0.0500(5) Uani 1 1 d . . . . .
F3 F 0.4413(3) 0.33095(15) -0.09859(9) 0.0510(5) Uani 1 1 d . . . . .
F4 F 0.3889(3) 0.59391(16) -0.12808(8) 0.0510(5) Uani 1 1 d . . . . .
D1 D 0.560(7) 0.279(5) 0.139(2) 0.124(18) Uiso 1 1 d . . . . .
D2 D 0.299(6) 0.970(4) 0.0045(17) 0.081(12) Uiso 1 1 d . . . . .
N1 N 0.6085(5) 0.3228(3) 0.18255(18) 0.0615(9) Uani 1 1 d . . . . .
O1 O 0.1838(3) 0.8288(2) -0.08605(11) 0.0485(6) Uani 1 1 d . . . . .
O2 O 0.3142(3) 0.87107(19) 0.01647(11) 0.0436(6) Uani 1 1 d . . . . .
O3 O 0.2878(3) 0.12515(18) -0.01232(10) 0.0433(6) Uani 1 1 d . . . . .
O4 O 0.4408(3) 0.17411(19) 0.08456(10) 0.0446(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 1.202(3) . ?
C1 O2 1.304(3) . ?
C1 C2 1.505(3) . ?
C2 C3 1.379(4) . ?
C2 C8 1.389(4) . ?
C3 F1 1.346(3) . ?
C3 C4 1.372(4) . ?
C4 F2 1.352(3) . ?
C4 C5 1.377(4) . ?
C5 C7 1.375(4) . ?
C5 C6 1.530(3) . ?
C6 O4 1.235(3) . ?
C6 O3 1.252(3) . ?
C7 F3 1.345(3) . ?
C7 C8 1.376(4) . ?
C8 F4 1.341(3) . ?
C9 N1 1.332(5) . ?
C9 C10 1.363(6) . ?
C10 C11 1.366(5) . ?
C11 C12 1.376(4) . ?
C12 C13 1.375(4) . ?
C12 C14 1.496(5) . ?
C13 N1 1.331(5) . ?

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 O2 125.9(2) . . ?
O1 C1 C2 122.2(3) . . ?
O2 C1 C2 111.9(2) . . ?
C3 C2 C8 116.0(2) . . ?
C3 C2 C1 123.0(2) . . ?
C8 C2 C1 121.0(2) . . ?
F1 C3 C4 118.2(2) . . ?
F1 C3 C2 119.6(2) . . ?
C4 C3 C2 122.1(2) . . ?
F2 C4 C3 118.0(2) . . ?
F2 C4 C5 120.1(2) . . ?
C3 C4 C5 121.9(2) . . ?
C7 C5 C4 116.2(2) . . ?
C7 C5 C6 121.6(2) . . ?
C4 C5 C6 122.2(2) . . ?
O4 C6 O3 127.2(2) . . ?
O4 C6 C5 118.1(2) . . ?
O3 C6 C5 114.7(2) . . ?
F3 C7 C5 120.0(2) . . ?
F3 C7 C8 117.8(2) . . ?
C5 C7 C8 122.2(2) . . ?
F4 C8 C7 118.5(2) . . ?
F4 C8 C2 120.0(2) . . ?
C7 C8 C2 121.4(2) . . ?
N1 C9 C10 119.8(4) . . ?
C9 C10 C11 118.8(4) . . ?
C10 C11 C12 121.4(3) . . ?
C13 C12 C11 117.3(3) . . ?
C13 C12 C14 120.5(3) . . ?
C11 C12 C14 122.2(3) . . ?
N1 C13 C12 120.6(3) . . ?
C13 N1 C9 122.1(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
O1 C1 C2 C3 -135.7(3) . . . . ?
O2 C1 C2 C3 44.8(4) . . . . ?
O1 C1 C2 C8 44.6(4) . . . . ?
O2 C1 C2 C8 -135.0(3) . . . . ?
C8 C2 C3 F1 -177.4(3) . . . . ?
C1 C2 C3 F1 2.8(4) . . . . ?
C8 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C4 -179.5(3) . . . . ?
F1 C3 C4 F2 -0.6(4) . . . . ?
C2 C3 C4 F2 -178.3(3) . . . . ?
F1 C3 C4 C5 178.0(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
F2 C4 C5 C7 178.2(3) . . . . ?
C3 C4 C5 C7 -0.4(4) . . . . ?
F2 C4 C5 C6 -0.9(4) . . . . ?
C3 C4 C5 C6 -179.5(3) . . . . ?
C7 C5 C6 O4 130.9(3) . . . . ?
C4 C5 C6 O4 -50.1(4) . . . . ?
C7 C5 C6 O3 -49.7(4) . . . . ?
C4 C5 C6 O3 129.3(3) . . . . ?
C4 C5 C7 F3 178.5(3) . . . . ?
C6 C5 C7 F3 -2.5(4) . . . . ?
C4 C5 C7 C8 0.0(4) . . . . ?
C6 C5 C7 C8 179.1(3) . . . . ?
F3 C7 C8 F4 0.8(4) . . . . ?
C5 C7 C8 F4 179.3(3) . . . . ?
F3 C7 C8 C2 -177.9(3) . . . . ?
C5 C7 C8 C2 0.6(5) . . . . ?
C3 C2 C8 F4 -179.4(3) . . . . ?
C1 C2 C8 F4 0.4(4) . . . . ?
C3 C2 C8 C7 -0.7(4) . . . . ?
C1 C2 C8 C7 179.0(3) . . . . ?
N1 C9 C10 C11 1.0(6) . . . . ?
C9 C10 C11 C12 -0.4(6) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C10 C11 C12 C14 178.6(4) . . . . ?
C11 C12 C13 N1 0.8(5) . . . . ?
C14 C12 C13 N1 -178.3(3) . . . . ?
C12 C13 N1 C9 -0.3(5) . . . . ?
C10 C9 N1 C13 -0.7(6) . . . . ?

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
O2 D2 O3 1.00(4) 1.54(4) 2.536(2) 177(4) 1_565
N1 D1 O4 1.00(5) 1.70(5) 2.674(4) 162(4) .
C13 H13 O3 0.93 2.52 3.296(4) 140.7 4
C13 H13 O1 0.93 2.60 3.097(4) 113.8 4_565
C10 H10 O1 0.93 2.49 3.339(4) 152.3 2_565

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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-D
_database_code_depnum_ccdc_archive 'CCDC 1911911'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C5 H13 D N'
_chemical_formula_sum            'C13 H13 D2 F4 N O4'
_chemical_formula_weight         327.26

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                   8.534(2)
_cell_length_b                   9.250(2)
_cell_length_c                   9.752(2)
_cell_angle_alpha                104.72(2)
_cell_angle_beta                 90.99(2)
_cell_angle_gamma                102.03(2)
_cell_volume                     726.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7529
_cell_measurement_theta_min      2.165
_cell_measurement_theta_max      29.312

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             336.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7529
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.165
_diffrn_reflns_theta_max         29.312
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3968
_reflns_number_gt                1785
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1864P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3393
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.3181
_refine_ls_wR_factor_gt          0.2482
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.5188(4) 0.2667(4) -0.0344(3) 0.0450(8) Uani 1 1 d . . . . .
C2 C 0.4739(3) 0.2587(4) 0.1127(3) 0.0389(7) Uani 1 1 d . . . . .
C3 C 0.5446(4) 0.1730(4) 0.1836(3) 0.0404(7) Uani 1 1 d . . . . .
C4 C 0.5142(4) 0.1694(4) 0.3215(3) 0.0420(8) Uani 1 1 d . . . . .
C5 C 0.4124(3) 0.2508(4) 0.3950(3) 0.0394(8) Uani 1 1 d . . . . .
C6 C 0.3714(4) 0.2447(4) 0.5452(3) 0.0433(8) Uani 1 1 d . . . . .
C7 C 0.3428(4) 0.3386(4) 0.3266(3) 0.0437(8) Uani 1 1 d . . . . .
C8 C 0.3712(4) 0.3414(4) 0.1884(3) 0.0430(8) Uani 1 1 d . . . . .
C9 C 1.1025(6) 0.5104(6) 0.7459(6) 0.0913(15) Uani 1 1 d . . . . .
H9A H 1.0227 0.5071 0.6739 0.137 Uiso 1 1 calc R U . . .
H9B H 1.1979 0.4887 0.7022 0.137 Uiso 1 1 calc R U . . .
H9C H 1.1275 0.6105 0.8112 0.137 Uiso 1 1 calc R U . . .
C10 C 1.0392(5) 0.3930(6) 0.8246(4) 0.0774(14) Uani 1 1 d . . . . .
H10A H 1.1182 0.4019 0.9008 0.093 Uiso 1 1 calc R U . . .
H10B H 0.9426 0.4159 0.8678 0.093 Uiso 1 1 calc R U . . .
C11 C 0.8667(5) 0.2055(7) 0.6328(5) 0.0902(15) Uani 1 1 d . . . . .
H11A H 0.8938 0.2663 0.5666 0.135 Uiso 1 1 calc R U . . .
H11B H 0.7745 0.2306 0.6802 0.135 Uiso 1 1 calc R U . . .
H11C H 0.8429 0.0989 0.5826 0.135 Uiso 1 1 calc R U . . .
C12 C 0.9845(7) 0.1331(8) 0.8386(6) 0.1045(19) Uani 1 1 d . . . . .
H12A H 1.0596 0.1818 0.9212 0.125 Uiso 1 1 calc R U . . .
H12B H 0.8769 0.1223 0.8709 0.125 Uiso 1 1 calc R U . . .
C13 C 1.0124(7) -0.0179(7) 0.7748(6) 0.0996(17) Uani 1 1 d . . . . .
H13A H 1.1198 -0.0086 0.7448 0.149 Uiso 1 1 calc R U . . .
H13B H 0.9370 -0.0680 0.6940 0.149 Uiso 1 1 calc R U . . .
H13C H 0.9990 -0.0772 0.8432 0.149 Uiso 1 1 calc R U . . .
F1 F 0.6427(3) 0.0864(3) 0.1175(2) 0.0614(7) Uani 1 1 d . . . . .
F2 F 0.5833(3) 0.0799(3) 0.3797(2) 0.0667(7) Uani 1 1 d . . . . .
F3 F 0.2411(3) 0.4208(3) 0.3936(2) 0.0609(7) Uani 1 1 d . . . . .
F4 F 0.2978(2) 0.4285(3) 0.13066(19) 0.0580(6) Uani 1 1 d . . . . .
D1A D 1.086(4) 0.217(4) 0.693(4) 0.054(10) Uiso 1 1 d . . . . .
N1 N 1.0025(4) 0.2372(4) 0.7378(3) 0.0595(9) Uani 1 1 d . . . . .
O1 O 0.4029(3) 0.2836(3) -0.1133(2) 0.0574(8) Uani 1 1 d . . . . .
O2 O 0.6497(3) 0.2580(4) -0.0701(3) 0.0691(9) Uani 1 1 d . . . . .
O3 O 0.4794(3) 0.3071(3) 0.6413(2) 0.0623(8) Uani 1 1 d . . . . .
O4 O 0.2313(3) 0.1799(3) 0.5555(2) 0.0561(7) Uani 1 1 d . . . . .
D1 D 0.444(5) 0.292(5) -0.198(5) 0.073(12) 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
C1 O2 1.188(4) . ?
C1 O1 1.301(4) . ?
C1 C2 1.508(4) . ?
C2 C8 1.383(4) . ?
C2 C3 1.391(4) . ?
C3 F1 1.340(3) . ?
C3 C4 1.381(4) . ?
C4 F2 1.337(3) . ?
C4 C5 1.362(4) . ?
C5 C7 1.385(4) . ?
C5 C6 1.525(4) . ?
C6 O4 1.238(4) . ?
C6 O3 1.239(4) . ?
C7 F3 1.342(4) . ?
C7 C8 1.379(4) . ?
C8 F4 1.336(4) . ?
C9 C10 1.502(7) . ?
C10 N1 1.441(5) . ?
C11 N1 1.464(6) . ?
C12 C13 1.448(8) . ?
C12 N1 1.530(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
O2 C1 O1 125.4(3) . . ?
O2 C1 C2 120.8(3) . . ?
O1 C1 C2 113.8(3) . . ?
C8 C2 C3 116.2(2) . . ?
C8 C2 C1 123.4(2) . . ?
C3 C2 C1 120.3(3) . . ?
F1 C3 C4 117.3(3) . . ?
F1 C3 C2 120.4(2) . . ?
C4 C3 C2 122.3(3) . . ?
F2 C4 C5 120.7(2) . . ?
F2 C4 C3 118.2(3) . . ?
C5 C4 C3 121.1(3) . . ?
C4 C5 C7 117.3(2) . . ?
C4 C5 C6 122.4(3) . . ?
C7 C5 C6 120.3(3) . . ?
O4 C6 O3 128.2(3) . . ?
O4 C6 C5 115.0(2) . . ?
O3 C6 C5 116.8(3) . . ?
F3 C7 C8 118.1(3) . . ?
F3 C7 C5 120.0(2) . . ?
C8 C7 C5 121.9(3) . . ?
F4 C8 C7 117.8(3) . . ?
F4 C8 C2 121.0(2) . . ?
C7 C8 C2 121.2(3) . . ?
N1 C10 C9 114.4(3) . . ?
C13 C12 N1 113.7(4) . . ?
C10 N1 C11 113.0(4) . . ?
C10 N1 C12 107.2(4) . . ?
C11 N1 C12 115.1(4) . . ?

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
O2 C1 C2 C8 144.9(4) . . . . ?
O1 C1 C2 C8 -35.1(5) . . . . ?
O2 C1 C2 C3 -30.7(5) . . . . ?
O1 C1 C2 C3 149.3(3) . . . . ?
C8 C2 C3 F1 178.4(3) . . . . ?
C1 C2 C3 F1 -5.7(5) . . . . ?
C8 C2 C3 C4 0.3(5) . . . . ?
C1 C2 C3 C4 176.2(3) . . . . ?
F1 C3 C4 F2 -0.3(5) . . . . ?
C2 C3 C4 F2 177.8(3) . . . . ?
F1 C3 C4 C5 -178.2(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
F2 C4 C5 C7 -178.7(3) . . . . ?
C3 C4 C5 C7 -0.9(5) . . . . ?
F2 C4 C5 C6 -0.2(5) . . . . ?
C3 C4 C5 C6 177.6(3) . . . . ?
C4 C5 C6 O4 -111.0(4) . . . . ?
C7 C5 C6 O4 67.5(4) . . . . ?
C4 C5 C6 O3 70.5(4) . . . . ?
C7 C5 C6 O3 -111.0(4) . . . . ?
C4 C5 C7 F3 179.7(3) . . . . ?
C6 C5 C7 F3 1.2(5) . . . . ?
C4 C5 C7 C8 1.7(5) . . . . ?
C6 C5 C7 C8 -176.9(3) . . . . ?
F3 C7 C8 F4 1.3(5) . . . . ?
C5 C7 C8 F4 179.4(3) . . . . ?
F3 C7 C8 C2 -179.6(3) . . . . ?
C5 C7 C8 C2 -1.5(5) . . . . ?
C3 C2 C8 F4 179.5(3) . . . . ?
C1 C2 C8 F4 3.8(5) . . . . ?
C3 C2 C8 C7 0.5(5) . . . . ?
C1 C2 C8 C7 -175.3(3) . . . . ?
C9 C10 N1 C11 -67.2(5) . . . . ?
C9 C10 N1 C12 165.0(4) . . . . ?
C13 C12 N1 C10 -156.2(5) . . . . ?
C13 C12 N1 C11 77.2(6) . . . . ?

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
O1 D1 O3 0.92(4) 1.64(4) 2.542(3) 168(4) 1_554
N1 D1A O4 0.87(4) 1.86(4) 2.707(4) 165(3) 1_655
C13 H13B O4 0.96 2.65 3.600(7) 169.3 2_656
C12 H12B O2 0.97 2.52 3.352(6) 143.7 1_556
C11 H11C O4 0.96 2.53 3.487(6) 177.3 2_656
C11 H11B O2 0.96 2.65 3.451(5) 141.3 1_556
C10 H10A F4 0.97 2.62 3.586(5) 171.8 1_656
C9 H9A F3 0.96 2.60 3.454(6) 148.9 2_666

_refine_diff_density_max         0.702
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_2-H
_database_code_depnum_ccdc_archive 'CCDC 1911912'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C9 H22 N'
_chemical_formula_sum            'C17 H23 F4 N O4'
_chemical_formula_weight         381.36

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      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                   8.4644(5)
_cell_length_b                   9.7485(15)
_cell_length_c                   12.6644(13)
_cell_angle_alpha                69.875(13)
_cell_angle_beta                 74.399(7)
_cell_angle_gamma                79.718(9)
_cell_volume                     940.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8374
_cell_measurement_theta_min      2.235
_cell_measurement_theta_max      2.235

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8374
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         29.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5240
_reflns_number_gt                2593
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0566P)²+0.1560P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4364
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.2110(2) 0.5587(2) 0.2885(2) 0.0396(5) Uani 1 1 d . . . . .
C2 C 0.1707(2) 0.4105(2) 0.29129(19) 0.0363(5) Uani 1 1 d . . . . .
C3 C 0.0457(2) 0.3356(2) 0.37533(19) 0.0372(5) Uani 1 1 d . . . . .
C4 C 0.0111(2) 0.2016(2) 0.37834(19) 0.0362(5) Uani 1 1 d . . . . .
C5 C 0.0996(2) 0.1325(2) 0.29837(18) 0.0343(5) Uani 1 1 d . . . . .
C6 C 0.0523(2) -0.0107(2) 0.3005(2) 0.0392(5) Uani 1 1 d . . . . .
C7 C 0.2255(2) 0.2076(2) 0.21523(19) 0.0387(5) Uani 1 1 d . . . . .
C8 C 0.2590(2) 0.3423(2) 0.2119(2) 0.0390(5) Uani 1 1 d . . . . .
C9 C 0.8198(4) 0.4047(3) 0.1170(3) 0.0845(10) Uani 1 1 d . . . . .
H9A H 0.9333 0.4071 0.1155 0.127 Uiso 1 1 calc R U . . .
H9B H 0.8118 0.3916 0.0470 0.127 Uiso 1 1 calc R U . . .
H9C H 0.7750 0.3248 0.1818 0.127 Uiso 1 1 calc R U . . .
C10 C 0.7233(3) 0.5486(3) 0.1279(3) 0.0629(7) Uani 1 1 d . . . . .
H10A H 0.7638 0.6286 0.0600 0.076 Uiso 1 1 calc R U . . .
H10B H 0.6079 0.5449 0.1321 0.076 Uiso 1 1 calc R U . . .
C11 C 0.7397(3) 0.5768(3) 0.2339(2) 0.0543(7) Uani 1 1 d . . . . .
H11A H 0.8499 0.6039 0.2209 0.065 Uiso 1 1 calc R U . . .
H11B H 0.7270 0.4867 0.2981 0.065 Uiso 1 1 calc R U . . .
C12 C 0.6384(3) 0.7108(3) 0.3764(2) 0.0525(6) Uani 1 1 d . . . . .
H12A H 0.6470 0.6139 0.4322 0.063 Uiso 1 1 calc R U . . .
H12B H 0.7408 0.7535 0.3602 0.063 Uiso 1 1 calc R U . . .
C13 C 0.5010(3) 0.8032(3) 0.4279(3) 0.0714(8) Uani 1 1 d . . . . .
H13A H 0.3971 0.7671 0.4367 0.086 Uiso 1 1 calc R U . . .
H13B H 0.5001 0.9033 0.3762 0.086 Uiso 1 1 calc R U . . .
C14 C 0.5180(4) 0.8016(3) 0.5451(3) 0.0711(8) Uani 1 1 d . . . . .
H14A H 0.5224 0.7023 0.5956 0.107 Uiso 1 1 calc R U . . .
H14B H 0.4249 0.8582 0.5776 0.107 Uiso 1 1 calc R U . . .
H14C H 0.6173 0.8433 0.5358 0.107 Uiso 1 1 calc R U . . .
C15 C 0.6100(3) 0.8387(3) 0.1700(2) 0.0528(6) Uani 1 1 d . . . . .
H15A H 0.5783 0.8212 0.1078 0.063 Uiso 1 1 calc R U . . .
H15B H 0.5251 0.9070 0.1980 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7700(3) 0.9088(3) 0.1221(3) 0.0765(9) Uani 1 1 d . . . . .
H16A H 0.8519 0.8478 0.0838 0.092 Uiso 1 1 calc R U . . .
H16B H 0.8097 0.9161 0.1849 0.092 Uiso 1 1 calc R U . . .
C17 C 0.7473(4) 1.0610(3) 0.0368(3) 0.0881(10) Uani 1 1 d . . . . .
H17A H 0.7067 1.0540 -0.0248 0.132 Uiso 1 1 calc R U . . .
H17B H 0.8511 1.1024 0.0059 0.132 Uiso 1 1 calc R U . . .
H17C H 0.6697 1.1227 0.0755 0.132 Uiso 1 1 calc R U . . .
F1 F 0.38144(16) 0.40974(15) 0.12615(13) 0.0602(4) Uani 1 1 d . . . . .
F2 F 0.31660(16) 0.15267(14) 0.13094(12) 0.0587(4) Uani 1 1 d . . . . .
F3 F -0.04599(15) 0.39443(14) 0.45652(13) 0.0576(4) Uani 1 1 d . . . . .
F4 F -0.11273(14) 0.13732(14) 0.46291(12) 0.0521(4) Uani 1 1 d . . . . .
H1 H 0.507(3) 0.661(3) 0.284(2) 0.072(8) Uiso 1 1 d . . . . .
H1A H 0.153(3) -0.190(4) 0.269(3) 0.104(11) Uiso 1 1 d . . . . .
N1 N 0.6164(2) 0.6958(2) 0.26648(18) 0.0471(5) Uani 1 1 d . . . . .
O1 O 0.17794(18) -0.09661(16) 0.26820(16) 0.0502(4) Uani 1 1 d . . . . .
O2 O -0.08831(19) -0.03764(19) 0.3300(2) 0.0709(6) Uani 1 1 d . . . . .
O3 O 0.34042(18) 0.55828(17) 0.31545(18) 0.0608(5) Uani 1 1 d . . . . .
O4 O 0.10830(19) 0.66474(16) 0.25956(16) 0.0553(5) 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 O3 1.231(2) . ?
C1 O4 1.244(2) . ?
C1 C2 1.529(3) . ?
C2 C8 1.374(3) . ?
C2 C3 1.386(3) . ?
C3 F3 1.344(2) . ?
C3 C4 1.375(3) . ?
C4 F4 1.344(2) . ?
C4 C5 1.386(3) . ?
C5 C7 1.388(3) . ?
C5 C6 1.509(3) . ?
C6 O2 1.196(2) . ?
C6 O1 1.297(2) . ?
C7 F2 1.351(2) . ?
C7 C8 1.377(3) . ?
C8 F1 1.354(2) . ?
C9 C10 1.522(4) . ?
C10 C11 1.505(4) . ?
C11 N1 1.507(3) . ?
C12 C13 1.486(3) . ?
C12 N1 1.511(3) . ?
C13 C14 1.524(4) . ?
C15 C16 1.508(3) . ?
C15 N1 1.508(3) . ?
C16 C17 1.520(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 O4 128.10(19) . . ?
O3 C1 C2 116.10(18) . . ?
O4 C1 C2 115.80(18) . . ?
C8 C2 C3 116.07(18) . . ?
C8 C2 C1 121.83(18) . . ?
C3 C2 C1 122.09(18) . . ?
F3 C3 C4 118.28(18) . . ?
F3 C3 C2 119.82(17) . . ?
C4 C3 C2 121.91(18) . . ?
F4 C4 C3 117.68(18) . . ?
F4 C4 C5 120.10(17) . . ?
C3 C4 C5 122.21(18) . . ?
C4 C5 C7 115.51(18) . . ?
C4 C5 C6 120.75(18) . . ?
C7 C5 C6 123.66(18) . . ?
O2 C6 O1 125.59(19) . . ?
O2 C6 C5 121.29(18) . . ?
O1 C6 C5 113.12(17) . . ?
F2 C7 C8 117.25(18) . . ?
F2 C7 C5 120.59(18) . . ?
C8 C7 C5 122.11(19) . . ?
F1 C8 C2 119.51(17) . . ?
F1 C8 C7 118.29(18) . . ?
C2 C8 C7 122.19(18) . . ?
C11 C10 C9 111.1(2) . . ?
C10 C11 N1 113.9(2) . . ?
C13 C12 N1 113.18(19) . . ?
C12 C13 C14 111.5(2) . . ?
C16 C15 N1 114.3(2) . . ?
C15 C16 C17 110.9(2) . . ?
C11 N1 C15 114.54(19) . . ?
C11 N1 C12 109.71(18) . . ?
C15 N1 C12 114.35(18) . . ?

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
O3 C1 C2 C8 -70.3(3) . . . . ?
O4 C1 C2 C8 110.0(2) . . . . ?
O3 C1 C2 C3 108.3(2) . . . . ?
O4 C1 C2 C3 -71.5(3) . . . . ?
C8 C2 C3 F3 179.70(19) . . . . ?
C1 C2 C3 F3 1.1(3) . . . . ?
C8 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
F3 C3 C4 F4 -0.1(3) . . . . ?
C2 C3 C4 F4 -179.83(19) . . . . ?
F3 C3 C4 C5 -179.76(19) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
F4 C4 C5 C7 -179.53(18) . . . . ?
C3 C4 C5 C7 0.1(3) . . . . ?
F4 C4 C5 C6 3.7(3) . . . . ?
C3 C4 C5 C6 -176.7(2) . . . . ?
C4 C5 C6 O2 32.9(3) . . . . ?
C7 C5 C6 O2 -143.6(2) . . . . ?
C4 C5 C6 O1 -146.7(2) . . . . ?
C7 C5 C6 O1 36.8(3) . . . . ?
C4 C5 C7 F2 -178.01(19) . . . . ?
C6 C5 C7 F2 -1.3(3) . . . . ?
C4 C5 C7 C8 -0.6(3) . . . . ?
C6 C5 C7 C8 176.1(2) . . . . ?
C3 C2 C8 F1 179.00(19) . . . . ?
C1 C2 C8 F1 -2.4(3) . . . . ?
C3 C2 C8 C7 0.1(3) . . . . ?
C1 C2 C8 C7 178.7(2) . . . . ?
F2 C7 C8 F1 -0.9(3) . . . . ?
C5 C7 C8 F1 -178.38(19) . . . . ?
F2 C7 C8 C2 178.0(2) . . . . ?
C5 C7 C8 C2 0.5(4) . . . . ?
C9 C10 C11 N1 -165.8(2) . . . . ?
N1 C12 C13 C14 173.6(2) . . . . ?
N1 C15 C16 C17 -172.5(2) . . . . ?
C10 C11 N1 C15 -52.4(3) . . . . ?
C10 C11 N1 C12 177.5(2) . . . . ?
C16 C15 N1 C11 -60.4(3) . . . . ?
C16 C15 N1 C12 67.4(3) . . . . ?
C13 C12 N1 C11 -168.1(2) . . . . ?
C13 C12 N1 C15 61.6(3) . . . . ?

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
C10 H10B F1 0.97 2.54 3.414(3) 149.6 .
C11 H11A O4 0.97 2.57 3.502(3) 160.6 1_655
C12 H12B O2 0.97 2.57 3.466(3) 153.7 1_665
C13 H13A F4 0.97 2.58 3.237(3) 125.3 2_566
C16 H16B O2 0.97 2.43 3.393(4) 173.7 1_665
N1 H1 O3 0.99(3) 1.75(3) 2.722(2) 166(2) .
O1 H1A O4 0.96(3) 1.59(3) 2.544(2) 174(3) 1_545
O1 H1A O3 0.96(3) 2.65(3) 3.313(2) 127(2) 1_545

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_7-H
_database_code_depnum_ccdc_archive 'CCDC 1911922'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C2 H8 N'
_chemical_formula_sum            'C10 H9 F4 N O4'
_chemical_formula_weight         283.18

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                   9.6384(15)
_cell_length_b                   7.9971(14)
_cell_length_c                   15.099(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.642(17)
_cell_angle_gamma                90
_cell_volume                     1147.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8306
_cell_measurement_theta_min      2.143
_cell_measurement_theta_max      29.548

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8306
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.143
_diffrn_reflns_theta_max         29.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3209
_reflns_number_gt                1897
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0759P)²+0.1192P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2826
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1602
_refine_ls_wR_factor_gt          0.1335
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.39951(17) 0.2598(2) 0.23493(13) 0.0329(4) Uani 1 1 d . . . . .
C2 C 0.35773(19) 0.2034(2) 0.31285(13) 0.0362(5) Uani 1 1 d . . . . .
C3 C 0.22249(19) 0.2287(2) 0.32878(13) 0.0352(5) Uani 1 1 d . . . . .
C4 C 0.12457(18) 0.3160(2) 0.26941(13) 0.0326(4) Uani 1 1 d . . . . .
C5 C -0.02024(19) 0.3515(2) 0.29176(14) 0.0362(5) Uani 1 1 d . . . . .
C6 C 0.16636(18) 0.3706(2) 0.19166(13) 0.0338(4) Uani 1 1 d . . . . .
C7 C 0.30047(19) 0.3408(2) 0.17412(12) 0.0333(4) Uani 1 1 d . . . . .
C8 C 0.54776(19) 0.2362(2) 0.21699(14) 0.0371(5) Uani 1 1 d . . . . .
C9 C 0.8114(4) 0.2757(3) 0.01219(18) 0.0698(8) Uani 1 1 d . . . . .
H9A H 0.7246 0.3299 -0.0123 0.105 Uiso 1 1 calc R U . . .
H9B H 0.8670 0.2604 -0.0343 0.105 Uiso 1 1 calc R U . . .
H9C H 0.8623 0.3436 0.0591 0.105 Uiso 1 1 calc R U . . .
C10 C 0.7052(3) 0.0016(3) -0.01988(16) 0.0590(7) Uani 1 1 d . . . . .
H10A H 0.7656 -0.0288 -0.0618 0.088 Uiso 1 1 calc R U . . .
H10B H 0.6236 0.0582 -0.0511 0.088 Uiso 1 1 calc R U . . .
H10C H 0.6767 -0.0973 0.0083 0.088 Uiso 1 1 calc R U . . .
F1 F 0.33267(12) 0.39714(16) 0.09627(8) 0.0480(4) Uani 1 1 d . . . . .
F2 F 0.07747(12) 0.45918(17) 0.13085(9) 0.0541(4) Uani 1 1 d . . . . .
F3 F 0.44780(13) 0.12059(18) 0.37477(9) 0.0595(4) Uani 1 1 d . . . . .
F4 F 0.18728(13) 0.16628(17) 0.40495(8) 0.0510(4) Uani 1 1 d . . . . .
H1 H 0.745(3) 0.292(4) 0.261(2) 0.115(12) Uiso 1 1 d . . . . .
N1 N 0.78146(19) 0.1128(2) 0.04881(12) 0.0470(5) Uani 1 1 d . . . . .
H1A H 0.7304 0.1276 0.0922 0.056 Uiso 1 1 calc R U . . .
H1B H 0.8621 0.0646 0.0731 0.056 Uiso 1 1 calc R U . . .
O1 O 0.64081(14) 0.3049(2) 0.27594(11) 0.0573(5) Uani 1 1 d . . . . .
O2 O 0.56814(15) 0.1591(2) 0.15138(11) 0.0578(5) Uani 1 1 d . . . . .
O3 O -0.02714(14) 0.43829(19) 0.35792(10) 0.0491(4) Uani 1 1 d . . . . .
O4 O -0.12059(14) 0.2859(2) 0.23858(11) 0.0514(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 C7 1.371(3) . ?
C1 C2 1.381(3) . ?
C1 C8 1.510(2) . ?
C2 F3 1.340(2) . ?
C2 C3 1.380(2) . ?
C3 F4 1.348(2) . ?
C3 C4 1.377(3) . ?
C4 C6 1.375(3) . ?
C4 C5 1.517(2) . ?
C5 O3 1.227(2) . ?
C5 O4 1.263(2) . ?
C6 F2 1.347(2) . ?
C6 C7 1.383(2) . ?
C7 F1 1.343(2) . ?
C8 O2 1.211(2) . ?
C8 O1 1.277(2) . ?
C9 N1 1.462(3) . ?
C10 N1 1.467(3) . ?

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
C7 C1 C2 117.06(15) . . ?
C7 C1 C8 120.82(17) . . ?
C2 C1 C8 122.12(18) . . ?
F3 C2 C3 118.14(17) . . ?
F3 C2 C1 120.56(16) . . ?
C3 C2 C1 121.29(18) . . ?
F4 C3 C4 119.99(15) . . ?
F4 C3 C2 118.33(17) . . ?
C4 C3 C2 121.68(17) . . ?
C6 C4 C3 116.74(15) . . ?
C6 C4 C5 122.86(17) . . ?
C3 C4 C5 120.38(16) . . ?
O3 C5 O4 127.76(17) . . ?
O3 C5 C4 117.68(17) . . ?
O4 C5 C4 114.57(17) . . ?
F2 C6 C4 120.35(15) . . ?
F2 C6 C7 117.92(16) . . ?
C4 C6 C7 121.72(18) . . ?
F1 C7 C1 120.51(15) . . ?
F1 C7 C6 118.06(17) . . ?
C1 C7 C6 121.42(17) . . ?
O2 C8 O1 126.75(17) . . ?
O2 C8 C1 119.90(18) . . ?
O1 C8 C1 113.35(16) . . ?
C9 N1 C10 112.32(19) . . ?

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 C1 C2 F3 178.84(17) . . . . ?
C8 C1 C2 F3 -1.9(3) . . . . ?
C7 C1 C2 C3 -0.4(3) . . . . ?
C8 C1 C2 C3 178.83(18) . . . . ?
F3 C2 C3 F4 -1.2(3) . . . . ?
C1 C2 C3 F4 178.07(17) . . . . ?
F3 C2 C3 C4 178.52(17) . . . . ?
C1 C2 C3 C4 -2.2(3) . . . . ?
F4 C3 C4 C6 -177.68(17) . . . . ?
C2 C3 C4 C6 2.6(3) . . . . ?
F4 C3 C4 C5 3.8(3) . . . . ?
C2 C3 C4 C5 -175.95(18) . . . . ?
C6 C4 C5 O3 -116.1(2) . . . . ?
C3 C4 C5 O3 62.4(2) . . . . ?
C6 C4 C5 O4 64.1(2) . . . . ?
C3 C4 C5 O4 -117.4(2) . . . . ?
C3 C4 C6 F2 -178.90(17) . . . . ?
C5 C4 C6 F2 -0.4(3) . . . . ?
C3 C4 C6 C7 -0.5(3) . . . . ?
C5 C4 C6 C7 178.02(18) . . . . ?
C2 C1 C7 F1 -179.09(17) . . . . ?
C8 C1 C7 F1 1.7(3) . . . . ?
C2 C1 C7 C6 2.5(3) . . . . ?
C8 C1 C7 C6 -176.74(18) . . . . ?
F2 C6 C7 F1 -2.1(3) . . . . ?
C4 C6 C7 F1 179.45(17) . . . . ?
F2 C6 C7 C1 176.34(16) . . . . ?
C4 C6 C7 C1 -2.1(3) . . . . ?
C7 C1 C8 O2 -60.0(3) . . . . ?
C2 C1 C8 O2 120.8(2) . . . . ?
C7 C1 C8 O1 119.6(2) . . . . ?
C2 C1 C8 O1 -59.6(3) . . . . ?

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
C9 H9A F1 0.96 2.54 3.270(3) 133.1 3_665
C9 H9B O3 0.96 2.60 3.463(3) 149.4 4_665
C9 H9C F2 0.96 2.36 3.225(3) 149.4 1_655
C10 H10A O3 0.96 2.61 3.447(3) 146.3 4_665
C10 H10C F4 0.96 2.54 3.267(3) 132.9 2_645
O1 H1 O4 1.08(3) 1.39(3) 2.4626(19) 176(3) 1_655
N1 H1A O2 0.89 1.94 2.798(2) 160.4 .
N1 H1B O3 0.89 2.02 2.902(2) 170.8 2_645

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_3-D
_database_code_depnum_ccdc_archive 'CCDC 1911915'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C5 H5 D N'
_chemical_formula_sum            'C13 H5 D2 F4 N O4'
_chemical_formula_weight         319.20

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.2513(6)
_cell_length_b                   9.6741(8)
_cell_length_c                   18.5924(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1304.25(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4644
_cell_measurement_theta_min      2.191
_cell_measurement_theta_max      29.574

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             640.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4644
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3656
_reflns_number_gt                1957
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.597
_reflns_Friedel_fraction_max     0.702
_reflns_Friedel_fraction_full    0.939

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0502P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 622 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2907
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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 0.1652(4) 1.2892(3) 0.96690(16) 0.0336(7) Uani 1 1 d . . . . .
C2 C 0.1937(4) 1.1372(3) 0.98360(15) 0.0306(7) Uani 1 1 d . . . . .
C3 C 0.1540(4) 1.0821(3) 1.05007(15) 0.0324(7) Uani 1 1 d . . . . .
C4 C 0.1826(4) 0.9454(3) 1.06565(15) 0.0332(7) Uani 1 1 d . . . . .
C5 C 0.2515(4) 0.8543(3) 1.01519(15) 0.0312(7) Uani 1 1 d . . . . .
C6 C 0.2773(4) 0.7048(3) 1.03282(16) 0.0343(7) Uani 1 1 d . . . . .
C7 C 0.2918(4) 0.9101(3) 0.94857(15) 0.0329(7) Uani 1 1 d . . . . .
C8 C 0.2632(4) 1.0470(3) 0.93381(15) 0.0325(7) Uani 1 1 d . . . . .
C9 C 0.2668(8) 0.4091(5) 0.17709(19) 0.0731(14) Uani 1 1 d . . . . .
H9 H 0.2190 0.4184 0.1309 0.088 Uiso 1 1 calc R U . . .
C10 C 0.1876(6) 0.4775(4) 0.2335(2) 0.0720(12) Uani 1 1 d . . . . .
H10 H 0.0856 0.5340 0.2263 0.086 Uiso 1 1 calc R U . . .
C11 C 0.2596(6) 0.4615(4) 0.29925(19) 0.0638(11) Uani 1 1 d . . . . .
H11 H 0.2072 0.5072 0.3382 0.077 Uiso 1 1 calc R U . . .
C12 C 0.4053(6) 0.3807(5) 0.3092(2) 0.0733(13) Uani 1 1 d . . . . .
H12 H 0.4542 0.3696 0.3551 0.088 Uiso 1 1 calc R U . . .
C13 C 0.4805(6) 0.3165(5) 0.2545(3) 0.0834(13) Uani 1 1 d . . . . .
H13 H 0.5834 0.2606 0.2614 0.100 Uiso 1 1 calc R U . . .
F1 F 0.0809(3) 1.16202(18) 1.10166(9) 0.0483(5) Uani 1 1 d . . . . .
F2 F 0.1375(3) 0.90013(18) 1.13156(9) 0.0489(5) Uani 1 1 d . . . . .
F3 F 0.3104(3) 1.09273(18) 0.86819(9) 0.0493(5) Uani 1 1 d . . . . .
F4 F 0.3661(3) 0.83034(19) 0.89773(9) 0.0506(5) Uani 1 1 d . . . . .
D1 D 0.444(8) 0.291(6) 0.148(3) 0.16(3) Uiso 1 1 d . . . . .
D3 D 0.218(6) 0.518(4) 0.9978(19) 0.082(12) Uiso 1 1 d . . . . .
N1 N 0.4087(6) 0.3314(4) 0.1885(2) 0.0757(13) Uani 1 1 d . . . . .
O1 O 0.0813(3) 1.3198(2) 0.91195(12) 0.0489(6) Uani 1 1 d . . . . .
O2 O 0.2346(3) 1.3707(2) 1.01162(11) 0.0464(6) Uani 1 1 d . . . . .
O3 O 0.2124(3) 0.6243(2) 0.98262(11) 0.0453(6) Uani 1 1 d . . . . .
O4 O 0.3477(3) 0.6671(2) 1.08752(12) 0.0530(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
C1 O1 1.225(4) . ?
C1 O2 1.252(3) . ?
C1 C2 1.517(4) . ?
C2 C8 1.368(4) . ?
C2 C3 1.376(4) . ?
C3 F1 1.341(3) . ?
C3 C4 1.370(4) . ?
C4 F2 1.342(3) . ?
C4 C5 1.381(4) . ?
C5 C7 1.383(4) . ?
C5 C6 1.494(4) . ?
C6 O4 1.195(3) . ?
C6 O3 1.304(4) . ?
C7 F4 1.334(3) . ?
C7 C8 1.368(4) . ?
C8 F3 1.342(3) . ?
C9 N1 1.292(6) . ?
C9 C10 1.365(6) . ?
C10 C11 1.339(5) . ?
C11 C12 1.327(6) . ?
C12 C13 1.311(6) . ?
C13 N1 1.340(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
O1 C1 O2 127.0(3) . . ?
O1 C1 C2 118.2(3) . . ?
O2 C1 C2 114.8(3) . . ?
C8 C2 C3 115.9(3) . . ?
C8 C2 C1 122.0(3) . . ?
C3 C2 C1 122.1(3) . . ?
F1 C3 C4 117.7(3) . . ?
F1 C3 C2 120.1(3) . . ?
C4 C3 C2 122.2(3) . . ?
F2 C4 C3 118.1(3) . . ?
F2 C4 C5 120.0(3) . . ?
C3 C4 C5 121.8(3) . . ?
C4 C5 C7 115.8(3) . . ?
C4 C5 C6 120.9(3) . . ?
C7 C5 C6 123.2(3) . . ?
O4 C6 O3 125.5(3) . . ?
O4 C6 C5 122.4(3) . . ?
O3 C6 C5 112.1(3) . . ?
F4 C7 C8 118.6(3) . . ?
F4 C7 C5 119.6(3) . . ?
C8 C7 C5 121.7(3) . . ?
F3 C8 C7 117.6(3) . . ?
F3 C8 C2 119.9(3) . . ?
C7 C8 C2 122.5(3) . . ?
N1 C9 C10 119.3(4) . . ?
C11 C10 C9 118.8(4) . . ?
C12 C11 C10 120.4(4) . . ?
C13 C12 C11 120.1(4) . . ?
C12 C13 N1 119.8(4) . . ?
C9 N1 C13 121.5(4) . . ?

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
O1 C1 C2 C8 50.3(4) . . . . ?
O2 C1 C2 C8 -128.6(3) . . . . ?
O1 C1 C2 C3 -130.7(3) . . . . ?
O2 C1 C2 C3 50.3(4) . . . . ?
C8 C2 C3 F1 -178.3(2) . . . . ?
C1 C2 C3 F1 2.7(4) . . . . ?
C8 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C4 -178.8(3) . . . . ?
F1 C3 C4 F2 -0.6(4) . . . . ?
C2 C3 C4 F2 -179.1(2) . . . . ?
F1 C3 C4 C5 177.9(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
F2 C4 C5 C7 179.2(3) . . . . ?
C3 C4 C5 C7 0.8(4) . . . . ?
F2 C4 C5 C6 -0.1(4) . . . . ?
C3 C4 C5 C6 -178.5(3) . . . . ?
C4 C5 C6 O4 -45.9(4) . . . . ?
C7 C5 C6 O4 134.8(3) . . . . ?
C4 C5 C6 O3 133.2(3) . . . . ?
C7 C5 C6 O3 -46.1(4) . . . . ?
C4 C5 C7 F4 177.2(3) . . . . ?
C6 C5 C7 F4 -3.5(4) . . . . ?
C4 C5 C7 C8 -0.6(4) . . . . ?
C6 C5 C7 C8 178.7(3) . . . . ?
F4 C7 C8 F3 0.7(4) . . . . ?
C5 C7 C8 F3 178.5(3) . . . . ?
F4 C7 C8 C2 -177.7(3) . . . . ?
C5 C7 C8 C2 0.1(5) . . . . ?
C3 C2 C8 F3 -178.2(3) . . . . ?
C1 C2 C8 F3 0.8(4) . . . . ?
C3 C2 C8 C7 0.1(4) . . . . ?
C1 C2 C8 C7 179.1(3) . . . . ?
N1 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C11 C12 C13 N1 -0.7(7) . . . . ?
C10 C9 N1 C13 -0.2(6) . . . . ?
C12 C13 N1 C9 0.6(7) . . . . ?

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
O3 D3 O2 1.06(4) 1.46(4) 2.517(3) 174(4) 1_545
N1 D1 O1 0.88(6) 1.85(6) 2.683(4) 158(6) 4_566
C12 H12 O3 0.93 2.66 3.335(5) 129.9 2_564
C12 H12 O4 0.93 2.65 3.341(5) 131.3 3_646
C9 H9 O2 0.93 2.27 3.108(4) 149.8 1_544

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_6-H
_database_code_depnum_ccdc_archive 'CCDC 1911920'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C6 H8 N'
_chemical_formula_sum            'C14 H9 F4 N O4'
_chemical_formula_weight         331.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   9.6564(6)
_cell_length_b                   10.5717(8)
_cell_length_c                   13.3865(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.686(6)
_cell_angle_gamma                90
_cell_volume                     1354.28(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6736
_cell_measurement_theta_min      2.128
_cell_measurement_theta_max      29.486

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             672.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6736
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.128
_diffrn_reflns_theta_max         29.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3775
_reflns_number_gt                2246
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0668P)²+0.1703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3187
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.38241(16) 0.94081(18) 0.10834(13) 0.0319(4) Uani 1 1 d . . . . .
C2 C 0.23022(15) 0.95485(17) 0.12079(13) 0.0291(4) Uani 1 1 d . . . . .
C3 C 0.15526(17) 0.85142(18) 0.14807(14) 0.0335(4) Uani 1 1 d . . . . .
C4 C 0.01725(17) 0.86174(18) 0.16413(14) 0.0343(4) Uani 1 1 d . . . . .
C5 C -0.05399(16) 0.97482(18) 0.15305(13) 0.0317(4) Uani 1 1 d . . . . .
C6 C -0.20409(17) 0.98518(19) 0.17656(15) 0.0373(5) Uani 1 1 d . . . . .
C7 C 0.01838(16) 1.07702(17) 0.12221(14) 0.0328(4) Uani 1 1 d . . . . .
C8 C 0.15694(16) 1.06808(17) 0.10713(14) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.5282(2) 0.3473(2) 0.13934(16) 0.0439(5) Uani 1 1 d . . . . .
H9 H 0.4915 0.2678 0.1497 0.053 Uiso 1 1 calc R U . . .
C10 C 0.6530(2) 0.3580(2) 0.10199(16) 0.0436(5) Uani 1 1 d . . . . .
H10 H 0.7009 0.2857 0.0869 0.052 Uiso 1 1 calc R U . . .
C11 C 0.70772(19) 0.4764(2) 0.08674(15) 0.0411(5) Uani 1 1 d . . . . .
C12 C 0.6323(2) 0.5816(2) 0.10904(16) 0.0450(5) Uani 1 1 d . . . . .
H12 H 0.6657 0.6624 0.0987 0.054 Uiso 1 1 calc R U . . .
C13 C 0.5080(2) 0.5662(2) 0.14635(16) 0.0449(5) Uani 1 1 d . . . . .
H13 H 0.4575 0.6368 0.1616 0.054 Uiso 1 1 calc R U . . .
C14 C 0.8447(2) 0.4896(3) 0.0456(2) 0.0649(7) Uani 1 1 d . . . . .
H14A H 0.9203 0.4744 0.0985 0.097 Uiso 1 1 calc R U . . .
H14B H 0.8525 0.5736 0.0197 0.097 Uiso 1 1 calc R U . . .
H14C H 0.8486 0.4294 -0.0076 0.097 Uiso 1 1 calc R U . . .
F1 F 0.21653(10) 1.17318(11) 0.07679(11) 0.0531(4) Uani 1 1 d . . . . .
F2 F -0.04488(10) 1.18966(11) 0.10585(10) 0.0516(4) Uani 1 1 d . . . . .
F3 F 0.21400(11) 0.73716(11) 0.16263(11) 0.0565(4) Uani 1 1 d . . . . .
F4 F -0.04784(12) 0.75606(12) 0.18858(11) 0.0568(4) Uani 1 1 d . . . . .
H1 H 0.375(3) 0.446(3) 0.195(2) 0.083(8) Uiso 1 1 d . . . . .
H2 H 0.545(3) 1.035(3) 0.111(2) 0.095(10) Uiso 1 1 d . . . . .
N1 N 0.45918(17) 0.45115(17) 0.16092(12) 0.0408(4) Uani 1 1 d . . . . .
O1 O 0.43368(13) 0.84009(14) 0.09450(13) 0.0536(4) Uani 1 1 d . . . . .
O2 O 0.45071(13) 1.04765(13) 0.11733(11) 0.0431(4) Uani 1 1 d . . . . .
O3 O -0.22421(14) 0.94459(17) 0.25973(12) 0.0589(5) Uani 1 1 d . . . . .
O4 O -0.28929(12) 1.03471(16) 0.10979(11) 0.0522(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 1.199(2) . ?
C1 O2 1.305(2) . ?
C1 C2 1.508(2) . ?
C2 C3 1.387(2) . ?
C2 C8 1.390(2) . ?
C3 F3 1.338(2) . ?
C3 C4 1.382(2) . ?
C4 F4 1.344(2) . ?
C4 C5 1.377(3) . ?
C5 C7 1.380(2) . ?
C5 C6 1.528(2) . ?
C6 O3 1.233(2) . ?
C6 O4 1.246(2) . ?
C7 F2 1.343(2) . ?
C7 C8 1.383(2) . ?
C8 F1 1.339(2) . ?
C9 N1 1.335(3) . ?
C9 C10 1.370(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.384(3) . ?
C11 C14 1.506(3) . ?
C12 C13 1.369(3) . ?
C13 N1 1.328(3) . ?

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 O2 124.66(15) . . ?
O1 C1 C2 122.20(16) . . ?
O2 C1 C2 113.10(15) . . ?
C3 C2 C8 116.05(14) . . ?
C3 C2 C1 120.13(15) . . ?
C8 C2 C1 123.82(15) . . ?
F3 C3 C4 116.58(16) . . ?
F3 C3 C2 121.61(14) . . ?
C4 C3 C2 121.78(16) . . ?
F4 C4 C5 120.31(14) . . ?
F4 C4 C3 117.67(16) . . ?
C5 C4 C3 121.99(16) . . ?
C4 C5 C7 116.50(14) . . ?
C4 C5 C6 120.93(16) . . ?
C7 C5 C6 122.55(16) . . ?
O3 C6 O4 128.72(16) . . ?
O3 C6 C5 115.44(17) . . ?
O4 C6 C5 115.84(16) . . ?
F2 C7 C5 120.38(14) . . ?
F2 C7 C8 117.69(15) . . ?
C5 C7 C8 121.93(16) . . ?
F1 C8 C7 116.81(15) . . ?
F1 C8 C2 121.50(14) . . ?
C7 C8 C2 121.67(15) . . ?
N1 C9 C10 120.01(19) . . ?
C9 C10 C11 120.00(18) . . ?
C12 C11 C10 118.19(17) . . ?
C12 C11 C14 121.2(2) . . ?
C10 C11 C14 120.60(19) . . ?
C13 C12 C11 119.67(19) . . ?
N1 C13 C12 120.56(18) . . ?
C13 N1 C9 121.57(16) . . ?

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
O1 C1 C2 C3 20.3(3) . . . . ?
O2 C1 C2 C3 -157.69(16) . . . . ?
O1 C1 C2 C8 -160.14(19) . . . . ?
O2 C1 C2 C8 21.8(2) . . . . ?
C8 C2 C3 F3 179.50(17) . . . . ?
C1 C2 C3 F3 -0.9(3) . . . . ?
C8 C2 C3 C4 -2.2(3) . . . . ?
C1 C2 C3 C4 177.35(16) . . . . ?
F3 C3 C4 F4 -2.8(3) . . . . ?
C2 C3 C4 F4 178.83(16) . . . . ?
F3 C3 C4 C5 179.01(17) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
F4 C4 C5 C7 -176.37(16) . . . . ?
C3 C4 C5 C7 1.8(3) . . . . ?
F4 C4 C5 C6 5.1(3) . . . . ?
C3 C4 C5 C6 -176.79(16) . . . . ?
C4 C5 C6 O3 51.4(3) . . . . ?
C7 C5 C6 O3 -127.1(2) . . . . ?
C4 C5 C6 O4 -129.4(2) . . . . ?
C7 C5 C6 O4 52.1(3) . . . . ?
C4 C5 C7 F2 177.47(16) . . . . ?
C6 C5 C7 F2 -4.0(3) . . . . ?
C4 C5 C7 C8 -2.6(3) . . . . ?
C6 C5 C7 C8 175.96(17) . . . . ?
F2 C7 C8 F1 -0.3(3) . . . . ?
C5 C7 C8 F1 179.73(16) . . . . ?
F2 C7 C8 C2 -179.03(16) . . . . ?
C5 C7 C8 C2 1.0(3) . . . . ?
C3 C2 C8 F1 -177.25(16) . . . . ?
C1 C2 C8 F1 3.2(3) . . . . ?
C3 C2 C8 C7 1.4(3) . . . . ?
C1 C2 C8 C7 -178.14(16) . . . . ?
N1 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C9 C10 C11 C14 -179.9(2) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C14 C11 C12 C13 180.0(2) . . . . ?
C11 C12 C13 N1 -0.3(3) . . . . ?
C12 C13 N1 C9 -0.5(3) . . . . ?
C10 C9 N1 C13 0.5(3) . . . . ?

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
O2 H2 O4 0.93(3) 1.60(3) 2.5299(16) 171(3) 1_655
N1 H1 O3 0.99(3) 1.65(3) 2.632(2) 173(3) 2_545
C13 H13 O1 0.93 2.33 3.041(3) 133.2 .
C13 H13 F3 0.93 2.58 3.397(2) 146.8 .
C10 H10 F2 0.93 2.64 3.412(2) 141.2 1_645
C9 H9 O2 0.93 2.39 3.260(3) 155.5 1_545

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_7-D
_database_code_depnum_ccdc_archive 'CCDC 1911923'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C2 H6 D2 N'
_chemical_formula_sum            'C10 H6 D3 F4 N O4'
_chemical_formula_weight         286.19

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                   9.6821(9)
_cell_length_b                   8.0228(9)
_cell_length_c                   15.0539(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.715(9)
_cell_angle_gamma                90
_cell_volume                     1152.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5319
_cell_measurement_theta_min      2.134
_cell_measurement_theta_max      29.367

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5319
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.134
_diffrn_reflns_theta_max         29.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3176
_reflns_number_gt                1935
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0735P)²+0.2492P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2656
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1357
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1 C 1.0462(2) 0.7645(3) 0.21728(13) 0.0357(5) Uani 1 1 d . . . . .
C2 C 0.89867(19) 0.7409(2) 0.23545(12) 0.0316(4) Uani 1 1 d . . . . .
C3 C 0.8560(2) 0.7971(3) 0.31342(13) 0.0354(5) Uani 1 1 d . . . . .
C4 C 0.7216(2) 0.7718(2) 0.32903(12) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.62350(19) 0.6848(2) 0.26982(12) 0.0311(4) Uani 1 1 d . . . . .
C6 C 0.47889(19) 0.6488(3) 0.29210(13) 0.0344(4) Uani 1 1 d . . . . .
C7 C 0.66612(19) 0.6290(3) 0.19206(12) 0.0334(4) Uani 1 1 d . . . . .
C8 C 0.79928(19) 0.6591(3) 0.17446(12) 0.0320(4) Uani 1 1 d . . . . .
C9 C 0.3118(4) 0.7242(3) 0.01265(17) 0.0695(8) Uani 1 1 d . . . . .
H9A H 0.2255 0.6724 -0.0143 0.104 Uiso 1 1 calc R U . . .
H9B H 0.3586 0.6550 0.0605 0.104 Uiso 1 1 calc R U . . .
H9C H 0.3707 0.7385 -0.0321 0.104 Uiso 1 1 calc R U . . .
C10 C 0.2060(3) 0.9982(3) -0.01898(16) 0.0584(7) Uani 1 1 d . . . . .
H10A H 0.2663 1.0313 -0.0603 0.088 Uiso 1 1 calc R U . . .
H10B H 0.1757 1.0952 0.0098 0.088 Uiso 1 1 calc R U . . .
H10C H 0.1258 0.9409 -0.0512 0.088 Uiso 1 1 calc R U . . .
F1 F 0.83224(13) 0.60236(17) 0.09664(8) 0.0472(4) Uani 1 1 d . . . . .
F2 F 0.57718(13) 0.54076(18) 0.13112(8) 0.0525(4) Uani 1 1 d . . . . .
F3 F 0.94643(14) 0.8809(2) 0.37532(8) 0.0577(4) Uani 1 1 d . . . . .
F4 F 0.68577(13) 0.83479(17) 0.40530(8) 0.0498(4) Uani 1 1 d . . . . .
D1 D 1.238(3) 0.703(4) 0.2610(18) 0.090(10) Uiso 1 1 d . . . . .
N1 N 0.2820(2) 0.8875(2) 0.04912(12) 0.0477(5) Uani 1 1 d . . . . .
D1A D 0.2318 0.8729 0.0929 0.057 Uiso 1 1 calc R U . . .
D1B D 0.3625 0.9355 0.0732 0.057 Uiso 1 1 calc R U . . .
O1 O 1.13893(16) 0.6961(2) 0.27682(10) 0.0560(5) Uani 1 1 d . . . . .
O2 O 1.06739(16) 0.8409(2) 0.15179(11) 0.0582(5) Uani 1 1 d . . . . .
O3 O 0.47251(15) 0.5620(2) 0.35820(10) 0.0485(4) Uani 1 1 d . . . . .
O4 O 0.37851(15) 0.7135(2) 0.23914(10) 0.0502(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 O2 1.207(2) . ?
C1 O1 1.280(2) . ?
C1 C2 1.511(3) . ?
C2 C8 1.379(3) . ?
C2 C3 1.384(3) . ?
C3 F3 1.346(2) . ?
C3 C4 1.376(3) . ?
C4 F4 1.352(2) . ?
C4 C5 1.377(3) . ?
C5 C7 1.380(3) . ?
C5 C6 1.521(3) . ?
C6 O3 1.225(2) . ?
C6 O4 1.260(2) . ?
C7 F2 1.348(2) . ?
C7 C8 1.381(3) . ?
C8 F1 1.345(2) . ?
C9 N1 1.467(3) . ?
C10 N1 1.459(3) . ?

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
O2 C1 O1 126.40(18) . . ?
O2 C1 C2 120.50(18) . . ?
O1 C1 C2 113.10(16) . . ?
C8 C2 C3 116.43(17) . . ?
C8 C2 C1 120.93(17) . . ?
C3 C2 C1 122.63(18) . . ?
F3 C3 C4 118.62(17) . . ?
F3 C3 C2 119.85(17) . . ?
C4 C3 C2 121.52(18) . . ?
F4 C4 C3 118.36(17) . . ?
F4 C4 C5 119.43(16) . . ?
C3 C4 C5 122.21(17) . . ?
C4 C5 C7 116.18(17) . . ?
C4 C5 C6 120.87(16) . . ?
C7 C5 C6 122.91(17) . . ?
O3 C6 O4 127.52(18) . . ?
O3 C6 C5 117.49(17) . . ?
O4 C6 C5 114.99(17) . . ?
F2 C7 C5 119.97(16) . . ?
F2 C7 C8 118.12(16) . . ?
C5 C7 C8 121.91(18) . . ?
F1 C8 C2 119.99(16) . . ?
F1 C8 C7 118.32(17) . . ?
C2 C8 C7 121.66(17) . . ?
C10 N1 C9 112.84(18) . . ?

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
O2 C1 C2 C8 60.2(3) . . . . ?
O1 C1 C2 C8 -119.5(2) . . . . ?
O2 C1 C2 C3 -120.7(2) . . . . ?
O1 C1 C2 C3 59.7(3) . . . . ?
C8 C2 C3 F3 -178.71(17) . . . . ?
C1 C2 C3 F3 2.1(3) . . . . ?
C8 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 -178.96(19) . . . . ?
F3 C3 C4 F4 1.1(3) . . . . ?
C2 C3 C4 F4 -177.87(18) . . . . ?
F3 C3 C4 C5 -178.86(18) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
F4 C4 C5 C7 177.92(17) . . . . ?
C3 C4 C5 C7 -2.1(3) . . . . ?
F4 C4 C5 C6 -4.2(3) . . . . ?
C3 C4 C5 C6 175.79(19) . . . . ?
C4 C5 C6 O3 -62.6(3) . . . . ?
C7 C5 C6 O3 115.2(2) . . . . ?
C4 C5 C6 O4 117.4(2) . . . . ?
C7 C5 C6 O4 -64.8(3) . . . . ?
C4 C5 C7 F2 179.04(17) . . . . ?
C6 C5 C7 F2 1.2(3) . . . . ?
C4 C5 C7 C8 -0.2(3) . . . . ?
C6 C5 C7 C8 -178.11(19) . . . . ?
C3 C2 C8 F1 179.31(17) . . . . ?
C1 C2 C8 F1 -1.5(3) . . . . ?
C3 C2 C8 C7 -2.6(3) . . . . ?
C1 C2 C8 C7 176.63(19) . . . . ?
F2 C7 C8 F1 1.5(3) . . . . ?
C5 C7 C8 F1 -179.20(17) . . . . ?
F2 C7 C8 C2 -176.62(17) . . . . ?
C5 C7 C8 C2 2.7(3) . . . . ?

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
N1 D1B O3 0.89 2.02 2.905(2) 170.8 2_655
N1 D1A O2 0.89 1.97 2.816(2) 159.5 1_455
O1 D1 O4 1.03(3) 1.46(3) 2.483(2) 180(3) 1_655
C10 H10B F4 0.96 2.56 3.273(3) 131.3 2_655
C10 H10A O3 0.96 2.62 3.453(3) 145.0 4_575
C9 H9C O3 0.96 2.61 3.463(3) 148.2 4_575
C9 H9B F2 0.96 2.39 3.226(3) 145.9 .
C9 H9A F1 0.96 2.54 3.278(3) 133.3 3_665

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_3-H
_database_code_depnum_ccdc_archive 'CCDC 1911914'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C5 H6 N'
_chemical_formula_sum            'C13 H7 F4 N O4'
_chemical_formula_weight         317.20

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.2625(8)
_cell_length_b                   9.6940(10)
_cell_length_c                   18.657(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1313.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10157
_cell_measurement_theta_min      2.183
_cell_measurement_theta_max      29.555

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             640.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10157
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.183
_diffrn_reflns_theta_max         29.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3671
_reflns_number_gt                2296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_max     0.845
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0656P)²+0.0584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.5(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3250
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.1656(5) 0.7882(3) 0.96676(18) 0.0379(8) Uani 1 1 d . . . . .
C2 C 0.1939(4) 0.6366(3) 0.98342(17) 0.0333(7) Uani 1 1 d . . . . .
C3 C 0.2645(4) 0.5462(3) 0.93381(17) 0.0360(7) Uani 1 1 d . . . . .
C4 C 0.2926(4) 0.4087(3) 0.94866(17) 0.0365(7) Uani 1 1 d . . . . .
C5 C 0.2521(4) 0.3535(3) 1.01504(17) 0.0341(7) Uani 1 1 d . . . . .
C6 C 0.2774(5) 0.2037(3) 1.03251(18) 0.0380(7) Uani 1 1 d . . . . .
C7 C 0.1831(4) 0.4445(3) 1.06547(18) 0.0355(7) Uani 1 1 d . . . . .
C8 C 0.1543(4) 0.5816(3) 1.04984(16) 0.0352(7) Uani 1 1 d . . . . .
C9 C 0.2666(9) 0.9102(5) 0.1776(2) 0.0765(15) Uani 1 1 d . . . . .
H9 H 0.2197 0.9206 0.1315 0.092 Uiso 1 1 calc R U . . .
C10 C 0.1874(7) 0.9765(5) 0.2337(3) 0.0757(14) Uani 1 1 d . . . . .
H10 H 0.0848 1.0322 0.2267 0.091 Uiso 1 1 calc R U . . .
C11 C 0.2590(7) 0.9608(5) 0.2996(2) 0.0702(13) Uani 1 1 d . . . . .
H11 H 0.2064 1.0067 0.3383 0.084 Uiso 1 1 calc R U . . .
C12 C 0.4059(7) 0.8792(6) 0.3100(2) 0.0771(14) Uani 1 1 d . . . . .
H12 H 0.4542 0.8676 0.3557 0.092 Uiso 1 1 calc R U . . .
C13 C 0.4813(7) 0.8156(6) 0.2548(4) 0.0849(15) Uani 1 1 d . . . . .
H13 H 0.5840 0.7597 0.2614 0.102 Uiso 1 1 calc R U . . .
F1 F 0.3105(3) 0.59197(19) 0.86793(10) 0.0524(6) Uani 1 1 d . . . . .
F2 F 0.3669(3) 0.3293(2) 0.89751(11) 0.0544(6) Uani 1 1 d . . . . .
F3 F 0.1382(3) 0.39949(19) 1.13131(11) 0.0519(6) Uani 1 1 d . . . . .
F4 F 0.0813(3) 0.66173(19) 1.10137(11) 0.0525(6) Uani 1 1 d . . . . .
N1 N 0.4094(8) 0.8317(4) 0.1892(3) 0.0817(16) Uani 1 1 d . . . . .
O1 O 0.0822(4) 0.8201(3) 0.91146(13) 0.0518(7) Uani 1 1 d . . . . .
O2 O 0.2349(4) 0.8702(2) 1.01124(13) 0.0490(7) Uani 1 1 d . . . . .
O3 O 0.2126(4) 0.1228(2) 0.98270(13) 0.0487(7) Uani 1 1 d . . . . .
O4 O 0.3490(4) 0.1666(3) 1.08758(14) 0.0558(7) Uani 1 1 d . . . . .
H1 H 0.449(7) 0.795(5) 0.157(3) 0.074(16) Uiso 1 1 d . . . . .
H3 H 0.234(7) 0.011(4) 0.9973(19) 0.074(13) 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
C1 O1 1.236(4) . ?
C1 O2 1.254(4) . ?
C1 C2 1.516(4) . ?
C2 C3 1.374(4) . ?
C2 C8 1.380(4) . ?
C3 F1 1.349(4) . ?
C3 C4 1.376(4) . ?
C4 F2 1.339(3) . ?
C4 C5 1.381(4) . ?
C5 C7 1.384(4) . ?
C5 C6 1.499(4) . ?
C6 O4 1.207(4) . ?
C6 O3 1.304(4) . ?
C7 F3 1.344(4) . ?
C7 C8 1.376(4) . ?
C8 F4 1.345(3) . ?
C9 N1 1.305(7) . ?
C9 C10 1.356(7) . ?
C10 C11 1.344(6) . ?
C11 C12 1.342(7) . ?
C12 C13 1.319(7) . ?
C13 N1 1.340(7) . ?

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 O2 126.2(3) . . ?
O1 C1 C2 118.7(3) . . ?
O2 C1 C2 115.1(3) . . ?
C3 C2 C8 115.8(3) . . ?
C3 C2 C1 122.1(3) . . ?
C8 C2 C1 122.1(3) . . ?
F1 C3 C2 119.7(3) . . ?
F1 C3 C4 117.7(3) . . ?
C2 C3 C4 122.5(3) . . ?
F2 C4 C3 118.2(3) . . ?
F2 C4 C5 120.1(3) . . ?
C3 C4 C5 121.6(3) . . ?
C4 C5 C7 116.1(3) . . ?
C4 C5 C6 123.0(3) . . ?
C7 C5 C6 120.9(3) . . ?
O4 C6 O3 125.6(3) . . ?
O4 C6 C5 121.8(3) . . ?
O3 C6 C5 112.6(3) . . ?
F3 C7 C8 118.1(3) . . ?
F3 C7 C5 120.1(3) . . ?
C8 C7 C5 121.8(3) . . ?
F4 C8 C7 117.8(3) . . ?
F4 C8 C2 120.0(3) . . ?
C7 C8 C2 122.1(3) . . ?
N1 C9 C10 119.0(4) . . ?
C11 C10 C9 119.3(5) . . ?
C12 C11 C10 120.4(4) . . ?
C13 C12 C11 119.6(5) . . ?
C12 C13 N1 119.8(5) . . ?
C9 N1 C13 122.0(4) . . ?

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
O1 C1 C2 C3 50.3(4) . . . . ?
O2 C1 C2 C3 -128.2(3) . . . . ?
O1 C1 C2 C8 -131.2(3) . . . . ?
O2 C1 C2 C8 50.2(4) . . . . ?
C8 C2 C3 F1 -178.7(3) . . . . ?
C1 C2 C3 F1 -0.1(5) . . . . ?
C8 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C4 179.2(3) . . . . ?
F1 C3 C4 F2 1.2(4) . . . . ?
C2 C3 C4 F2 -178.1(3) . . . . ?
F1 C3 C4 C5 179.0(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
F2 C4 C5 C7 177.3(3) . . . . ?
C3 C4 C5 C7 -0.4(5) . . . . ?
F2 C4 C5 C6 -3.6(5) . . . . ?
C3 C4 C5 C6 178.7(3) . . . . ?
C4 C5 C6 O4 134.6(4) . . . . ?
C7 C5 C6 O4 -46.3(5) . . . . ?
C4 C5 C6 O3 -46.0(4) . . . . ?
C7 C5 C6 O3 133.0(3) . . . . ?
C4 C5 C7 F3 179.4(3) . . . . ?
C6 C5 C7 F3 0.3(5) . . . . ?
C4 C5 C7 C8 0.9(5) . . . . ?
C6 C5 C7 C8 -178.2(3) . . . . ?
F3 C7 C8 F4 -0.6(4) . . . . ?
C5 C7 C8 F4 177.9(3) . . . . ?
F3 C7 C8 C2 -179.1(3) . . . . ?
C5 C7 C8 C2 -0.6(5) . . . . ?
C3 C2 C8 F4 -178.7(3) . . . . ?
C1 C2 C8 F4 2.7(5) . . . . ?
C3 C2 C8 C7 -0.2(5) . . . . ?
C1 C2 C8 C7 -178.8(3) . . . . ?
N1 C9 C10 C11 0.6(7) . . . . ?
C9 C10 C11 C12 -0.7(7) . . . . ?
C10 C11 C12 C13 0.8(8) . . . . ?
C11 C12 C13 N1 -0.8(8) . . . . ?
C10 C9 N1 C13 -0.6(7) . . . . ?
C12 C13 N1 C9 0.7(8) . . . . ?

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
C9 H9 O2 0.93 2.30 3.136(5) 149.5 1_554
C12 H12 O4 0.93 2.64 3.327(6) 131.4 3_656
N1 H1 O1 0.75(5) 1.95(5) 2.695(5) 168(5) 4_566
O3 H3 O2 1.13(4) 1.39(4) 2.511(3) 172(4) 1_545

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_4-H
_database_code_depnum_ccdc_archive 'CCDC 1911916'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C6 H8 N'
_chemical_formula_sum            'C14 H9 F4 N O4'
_chemical_formula_weight         331.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   9.7554(5)
_cell_length_b                   14.2346(8)
_cell_length_c                   9.7170(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.127(4)
_cell_angle_gamma                90
_cell_volume                     1332.26(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10834
_cell_measurement_theta_min      2.114
_cell_measurement_theta_max      29.603

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             672.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10834
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         29.603
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3747
_reflns_number_gt                2393
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0645P)²+0.2949P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3317
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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
C1 C 1.04206(17) 0.14723(12) 0.27585(15) 0.0295(4) Uani 1 1 d . . . . .
C2 C 1.01047(16) 0.13542(11) 0.42333(15) 0.0276(3) Uani 1 1 d . . . . .
C3 C 0.88051(17) 0.15275(12) 0.45809(15) 0.0299(4) Uani 1 1 d . . . . .
C4 C 0.85181(16) 0.13913(12) 0.59117(16) 0.0298(4) Uani 1 1 d . . . . .
C5 C 0.95254(17) 0.10870(11) 0.69866(15) 0.0272(3) Uani 1 1 d . . . . .
C6 C 0.91852(17) 0.09217(12) 0.84336(15) 0.0296(4) Uani 1 1 d . . . . .
C7 C 1.08276(17) 0.09315(11) 0.66496(15) 0.0282(4) Uani 1 1 d . . . . .
C8 C 1.11099(17) 0.10537(12) 0.53134(16) 0.0288(4) Uani 1 1 d . . . . .
C9 C 0.47727(18) 0.09542(14) 0.16552(19) 0.0387(4) Uani 1 1 d . . . . .
C10 C 0.5854(2) 0.10303(15) 0.0911(2) 0.0458(5) Uani 1 1 d . . . . .
H10 H 0.6710 0.0763 0.1255 0.055 Uiso 1 1 calc R U . . .
C11 C 0.5675(2) 0.15000(15) -0.0339(2) 0.0530(5) Uani 1 1 d . . . . .
H11 H 0.6410 0.1552 -0.0839 0.064 Uiso 1 1 calc R U . . .
C12 C 0.4405(2) 0.18953(16) -0.0855(2) 0.0522(5) Uani 1 1 d . . . . .
H12 H 0.4272 0.2210 -0.1704 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3356(2) 0.18162(14) -0.0100(2) 0.0447(5) Uani 1 1 d . . . . .
H13 H 0.2495 0.2082 -0.0427 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4843(3) 0.04654(19) 0.3020(2) 0.0618(6) Uani 1 1 d . . . . .
H14A H 0.4889 0.0923 0.3752 0.093 Uiso 1 1 calc R U . . .
H14B H 0.5655 0.0075 0.3178 0.093 Uiso 1 1 calc R U . . .
H14C H 0.4030 0.0084 0.3009 0.093 Uiso 1 1 calc R U . . .
F1 F 0.77777(10) 0.18655(9) 0.36211(10) 0.0465(3) Uani 1 1 d . . . . .
F2 F 0.72308(11) 0.15847(9) 0.61615(10) 0.0473(3) Uani 1 1 d . . . . .
F3 F 1.18727(10) 0.06342(8) 0.76216(10) 0.0418(3) Uani 1 1 d . . . . .
F4 F 1.24009(10) 0.08466(8) 0.50864(10) 0.0451(3) Uani 1 1 d . . . . .
H1 H 0.284(3) 0.1320(16) 0.165(2) 0.063(7) Uiso 1 1 d . . . . .
N1 N 0.35584(16) 0.13565(12) 0.11123(16) 0.0404(4) Uani 1 1 d . . . . .
O1 O 1.15616(13) 0.18098(9) 0.26238(12) 0.0406(3) Uani 1 1 d . . . . .
O2 O 0.94778(14) 0.12040(10) 0.18082(11) 0.0440(3) Uani 1 1 d . . . . .
O3 O 1.00202(14) 0.13570(10) 0.93905(12) 0.0420(3) Uani 1 1 d . . . . .
O4 O 0.82065(14) 0.04389(10) 0.85999(13) 0.0456(4) Uani 1 1 d . . . . .
H3 H 0.975(3) 0.130(2) 1.033(3) 0.112(11) 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
C1 O1 1.238(2) . ?
C1 O2 1.255(2) . ?
C1 C2 1.522(2) . ?
C2 C3 1.385(2) . ?
C2 C8 1.386(2) . ?
C3 F1 1.3451(18) . ?
C3 C4 1.379(2) . ?
C4 F2 1.3449(18) . ?
C4 C5 1.385(2) . ?
C5 C7 1.379(2) . ?
C5 C6 1.513(2) . ?
C6 O4 1.208(2) . ?
C6 O3 1.293(2) . ?
C7 F3 1.3436(17) . ?
C7 C8 1.380(2) . ?
C8 F4 1.3453(18) . ?
C9 N1 1.346(2) . ?
C9 C10 1.375(3) . ?
C9 C14 1.490(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.355(3) . ?
C13 N1 1.335(3) . ?

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 O2 127.33(14) . . ?
O1 C1 C2 117.52(14) . . ?
O2 C1 C2 115.15(14) . . ?
C3 C2 C8 115.82(13) . . ?
C3 C2 C1 122.67(14) . . ?
C8 C2 C1 121.51(14) . . ?
F1 C3 C4 117.42(14) . . ?
F1 C3 C2 120.32(13) . . ?
C4 C3 C2 122.23(14) . . ?
F2 C4 C3 118.33(14) . . ?
F2 C4 C5 119.93(13) . . ?
C3 C4 C5 121.71(15) . . ?
C7 C5 C4 116.18(14) . . ?
C7 C5 C6 122.80(14) . . ?
C4 C5 C6 121.02(14) . . ?
O4 C6 O3 126.70(15) . . ?
O4 C6 C5 120.48(14) . . ?
O3 C6 C5 112.80(14) . . ?
F3 C7 C5 120.56(13) . . ?
F3 C7 C8 117.29(14) . . ?
C5 C7 C8 122.13(14) . . ?
F4 C8 C7 117.27(14) . . ?
F4 C8 C2 120.80(13) . . ?
C7 C8 C2 121.91(15) . . ?
N1 C9 C10 117.48(18) . . ?
N1 C9 C14 117.45(18) . . ?
C10 C9 C14 125.06(18) . . ?
C11 C10 C9 120.21(18) . . ?
C10 C11 C12 120.01(19) . . ?
C13 C12 C11 118.8(2) . . ?
N1 C13 C12 119.97(18) . . ?
C13 N1 C9 123.54(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
O1 C1 C2 C3 141.01(17) . . . . ?
O2 C1 C2 C3 -39.5(2) . . . . ?
O1 C1 C2 C8 -39.7(2) . . . . ?
O2 C1 C2 C8 139.79(17) . . . . ?
C8 C2 C3 F1 176.75(15) . . . . ?
C1 C2 C3 F1 -3.9(2) . . . . ?
C8 C2 C3 C4 -1.3(2) . . . . ?
C1 C2 C3 C4 178.01(15) . . . . ?
F1 C3 C4 F2 1.3(2) . . . . ?
C2 C3 C4 F2 179.45(15) . . . . ?
F1 C3 C4 C5 -177.00(15) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
F2 C4 C5 C7 -178.13(15) . . . . ?
C3 C4 C5 C7 0.2(2) . . . . ?
F2 C4 C5 C6 3.0(2) . . . . ?
C3 C4 C5 C6 -178.71(15) . . . . ?
C7 C5 C6 O4 -127.71(19) . . . . ?
C4 C5 C6 O4 51.1(2) . . . . ?
C7 C5 C6 O3 53.5(2) . . . . ?
C4 C5 C6 O3 -127.73(17) . . . . ?
C4 C5 C7 F3 -179.91(15) . . . . ?
C6 C5 C7 F3 -1.1(2) . . . . ?
C4 C5 C7 C8 -1.2(2) . . . . ?
C6 C5 C7 C8 177.66(15) . . . . ?
F3 C7 C8 F4 1.3(2) . . . . ?
C5 C7 C8 F4 -177.41(15) . . . . ?
F3 C7 C8 C2 179.74(15) . . . . ?
C5 C7 C8 C2 1.0(3) . . . . ?
C3 C2 C8 F4 178.64(15) . . . . ?
C1 C2 C8 F4 -0.7(2) . . . . ?
C3 C2 C8 C7 0.3(2) . . . . ?
C1 C2 C8 C7 -179.05(15) . . . . ?
N1 C9 C10 C11 -0.2(3) . . . . ?
C14 C9 C10 C11 -179.9(2) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 N1 -0.5(3) . . . . ?
C12 C13 N1 C9 0.1(3) . . . . ?
C10 C9 N1 C13 0.3(3) . . . . ?
C14 C9 N1 C13 179.95(19) . . . . ?

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
O3 H3 O2 0.99(3) 1.51(3) 2.4982(16) 175(3) 1_556
N1 H1 O1 0.94(2) 1.82(3) 2.697(2) 154(2) 1_455
C14 H14C O4 0.96 2.58 3.391(3) 141.9 3_656
C13 H13 O3 0.93 2.61 3.279(2) 129.7 1_454
C13 H13 O1 0.93 2.52 3.248(2) 135.2 4_465
C10 H10 F3 0.93 2.56 3.400(2) 149.6 3_756

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_2-D
_database_code_depnum_ccdc_archive 'CCDC 1911913'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C9 H21 D N'
_chemical_formula_sum            'C17 H21 D2 F4 N O4'
_chemical_formula_weight         383.37

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                   8.4573(12)
_cell_length_b                   9.7338(14)
_cell_length_c                   12.660(2)
_cell_angle_alpha                69.848(14)
_cell_angle_beta                 74.392(13)
_cell_angle_gamma                79.621(12)
_cell_volume                     937.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8288
_cell_measurement_theta_min      2.239
_cell_measurement_theta_max      29.563

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8288
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.239
_diffrn_reflns_theta_max         29.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5268
_reflns_number_gt                2823
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0508P)²+0.2116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4379
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.4472(2) 1.01055(19) 0.19954(17) 0.0390(5) Uani 1 1 d . . . . .
C2 C 0.4004(2) 0.86693(17) 0.20158(16) 0.0345(4) Uani 1 1 d . . . . .
C3 C 0.2746(2) 0.79220(19) 0.28514(17) 0.0374(4) Uani 1 1 d . . . . .
C4 C 0.2410(2) 0.65726(19) 0.28815(17) 0.0389(4) Uani 1 1 d . . . . .
C5 C 0.3294(2) 0.58967(18) 0.20846(17) 0.0361(4) Uani 1 1 d . . . . .
C6 C 0.2893(2) 0.44077(19) 0.21159(18) 0.0401(5) Uani 1 1 d . . . . .
C7 C 0.4543(2) 0.66390(19) 0.12471(17) 0.0365(4) Uani 1 1 d . . . . .
C8 C 0.4890(2) 0.79860(18) 0.12184(16) 0.0351(4) Uani 1 1 d . . . . .
C9 C 0.6807(4) 0.5956(3) 0.3827(3) 0.0857(9) Uani 1 1 d . . . . .
H9A H 0.7240 0.6752 0.3170 0.128 Uiso 1 1 calc R U . . .
H9B H 0.6909 0.6099 0.4519 0.128 Uiso 1 1 calc R U . . .
H9C H 0.5665 0.5928 0.3861 0.128 Uiso 1 1 calc R U . . .
C10 C 0.7767(3) 0.4515(3) 0.3721(2) 0.0634(6) Uani 1 1 d . . . . .
H10A H 0.8921 0.4546 0.3683 0.076 Uiso 1 1 calc R U . . .
H10B H 0.7356 0.3714 0.4399 0.076 Uiso 1 1 calc R U . . .
C11 C 0.7604(3) 0.4238(2) 0.2656(2) 0.0532(6) Uani 1 1 d . . . . .
H11A H 0.6501 0.3972 0.2783 0.064 Uiso 1 1 calc R U . . .
H11B H 0.7736 0.5142 0.2015 0.064 Uiso 1 1 calc R U . . .
C12 C 0.8896(3) 0.1619(2) 0.3302(2) 0.0532(6) Uani 1 1 d . . . . .
H12A H 0.9754 0.0935 0.3026 0.064 Uiso 1 1 calc R U . . .
H12B H 0.9201 0.1798 0.3925 0.064 Uiso 1 1 calc R U . . .
C13 C 0.7305(3) 0.0916(3) 0.3770(2) 0.0757(8) Uani 1 1 d . . . . .
H13A H 0.6924 0.0831 0.3139 0.091 Uiso 1 1 calc R U . . .
H13B H 0.6473 0.1532 0.4142 0.091 Uiso 1 1 calc R U . . .
C14 C 0.7528(4) -0.0594(3) 0.4631(3) 0.0855(9) Uani 1 1 d . . . . .
H14A H 0.8247 -0.1239 0.4242 0.128 Uiso 1 1 calc R U . . .
H14B H 0.6475 -0.0978 0.4981 0.128 Uiso 1 1 calc R U . . .
H14C H 0.8002 -0.0523 0.5217 0.128 Uiso 1 1 calc R U . . .
C15 C 0.8611(3) 0.2900(2) 0.12330(19) 0.0515(5) Uani 1 1 d . . . . .
H15A H 0.7586 0.2474 0.1395 0.062 Uiso 1 1 calc R U . . .
H15B H 0.8525 0.3871 0.0674 0.062 Uiso 1 1 calc R U . . .
C16 C 0.9993(3) 0.1969(3) 0.0720(2) 0.0710(7) Uani 1 1 d . . . . .
H16A H 1.0006 0.0968 0.1239 0.085 Uiso 1 1 calc R U . . .
H16B H 1.1033 0.2333 0.0628 0.085 Uiso 1 1 calc R U . . .
C17 C 0.9813(3) 0.1981(3) -0.0451(2) 0.0700(7) Uani 1 1 d . . . . .
H17A H 0.8829 0.1547 -0.0352 0.105 Uiso 1 1 calc R U . . .
H17B H 1.0753 0.1429 -0.0784 0.105 Uiso 1 1 calc R U . . .
H17C H 0.9744 0.2977 -0.0953 0.105 Uiso 1 1 calc R U . . .
F1 F 0.61268(14) 0.86279(12) 0.03696(10) 0.0520(3) Uani 1 1 d . . . . .
F2 F 0.54606(15) 0.60550(12) 0.04360(11) 0.0578(4) Uani 1 1 d . . . . .
F3 F 0.18338(16) 0.84698(12) 0.36912(11) 0.0580(4) Uani 1 1 d . . . . .
F4 F 0.11862(15) 0.59001(13) 0.37395(11) 0.0599(4) Uani 1 1 d . . . . .
D1 D 0.985(3) 0.339(2) 0.2142(19) 0.059(6) Uiso 1 1 d . . . . .
D1A D 0.348(3) 1.188(3) 0.232(2) 0.095(9) Uiso 1 1 d . . . . .
N1 N 0.8833(2) 0.30478(18) 0.23327(16) 0.0464(4) Uani 1 1 d . . . . .
O1 O 0.32196(17) 1.09581(14) 0.23207(14) 0.0493(4) Uani 1 1 d . . . . .
O2 O 0.58845(19) 1.03751(17) 0.16944(17) 0.0699(5) Uani 1 1 d . . . . .
O3 O 0.16018(18) 0.44144(15) 0.18412(15) 0.0604(5) Uani 1 1 d . . . . .
O4 O 0.39188(18) 0.33531(14) 0.24147(15) 0.0562(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 O2 1.201(2) . ?
C1 O1 1.290(2) . ?
C1 C2 1.510(2) . ?
C2 C8 1.378(3) . ?
C2 C3 1.387(3) . ?
C3 F3 1.346(2) . ?
C3 C4 1.379(2) . ?
C4 F4 1.353(2) . ?
C4 C5 1.372(3) . ?
C5 C7 1.381(3) . ?
C5 C6 1.532(2) . ?
C6 O3 1.230(2) . ?
C6 O4 1.240(2) . ?
C7 F2 1.339(2) . ?
C7 C8 1.381(2) . ?
C8 F1 1.344(2) . ?
C9 C10 1.518(3) . ?
C10 C11 1.507(3) . ?
C11 N1 1.501(3) . ?
C12 C13 1.502(3) . ?
C12 N1 1.508(3) . ?
C13 C14 1.514(4) . ?
C15 C16 1.492(3) . ?
C15 N1 1.511(3) . ?
C16 C17 1.526(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 125.83(17) . . ?
O2 C1 C2 121.02(18) . . ?
O1 C1 C2 113.15(16) . . ?
C8 C2 C3 116.05(15) . . ?
C8 C2 C1 120.60(16) . . ?
C3 C2 C1 123.26(17) . . ?
F3 C3 C4 117.21(16) . . ?
F3 C3 C2 120.99(15) . . ?
C4 C3 C2 121.77(18) . . ?
F4 C4 C5 119.84(15) . . ?
F4 C4 C3 118.15(17) . . ?
C5 C4 C3 122.00(17) . . ?
C4 C5 C7 116.49(15) . . ?
C4 C5 C6 121.53(16) . . ?
C7 C5 C6 121.97(17) . . ?
O3 C6 O4 128.56(16) . . ?
O3 C6 C5 115.98(16) . . ?
O4 C6 C5 115.46(16) . . ?
F2 C7 C5 120.17(15) . . ?
F2 C7 C8 118.14(16) . . ?
C5 C7 C8 121.69(17) . . ?
F1 C8 C2 120.50(15) . . ?
F1 C8 C7 117.50(17) . . ?
C2 C8 C7 122.00(16) . . ?
C11 C10 C9 110.9(2) . . ?
N1 C11 C10 113.84(18) . . ?
C13 C12 N1 114.20(19) . . ?
C12 C13 C14 110.9(2) . . ?
C16 C15 N1 112.93(18) . . ?
C15 C16 C17 111.2(2) . . ?
C11 N1 C12 114.43(18) . . ?
C11 N1 C15 109.62(16) . . ?
C12 N1 C15 114.58(16) . . ?

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
O2 C1 C2 C8 -32.8(3) . . . . ?
O1 C1 C2 C8 146.93(18) . . . . ?
O2 C1 C2 C3 143.7(2) . . . . ?
O1 C1 C2 C3 -36.6(3) . . . . ?
C8 C2 C3 F3 178.12(17) . . . . ?
C1 C2 C3 F3 1.5(3) . . . . ?
C8 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 -176.38(18) . . . . ?
F3 C3 C4 F4 0.6(3) . . . . ?
C2 C3 C4 F4 178.57(17) . . . . ?
F3 C3 C4 C5 -178.31(17) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
F4 C4 C5 C7 -178.89(17) . . . . ?
C3 C4 C5 C7 0.0(3) . . . . ?
F4 C4 C5 C6 2.0(3) . . . . ?
C3 C4 C5 C6 -179.07(18) . . . . ?
C4 C5 C6 O3 70.9(3) . . . . ?
C7 C5 C6 O3 -108.1(2) . . . . ?
C4 C5 C6 O4 -109.2(2) . . . . ?
C7 C5 C6 O4 71.8(3) . . . . ?
C4 C5 C7 F2 -179.85(17) . . . . ?
C6 C5 C7 F2 -0.8(3) . . . . ?
C4 C5 C7 C8 0.4(3) . . . . ?
C6 C5 C7 C8 179.50(18) . . . . ?
C3 C2 C8 F1 179.53(16) . . . . ?
C1 C2 C8 F1 -3.8(3) . . . . ?
C3 C2 C8 C7 0.2(3) . . . . ?
C1 C2 C8 C7 176.91(17) . . . . ?
F2 C7 C8 F1 0.4(3) . . . . ?
C5 C7 C8 F1 -179.89(16) . . . . ?
F2 C7 C8 C2 179.72(16) . . . . ?
C5 C7 C8 C2 -0.6(3) . . . . ?
C9 C10 C11 N1 165.7(2) . . . . ?
N1 C12 C13 C14 173.0(2) . . . . ?
N1 C15 C16 C17 -173.97(19) . . . . ?
C10 C11 N1 C12 52.0(2) . . . . ?
C10 C11 N1 C15 -177.74(18) . . . . ?
C13 C12 N1 C11 61.1(3) . . . . ?
C13 C12 N1 C15 -66.7(3) . . . . ?
C16 C15 N1 C11 168.08(19) . . . . ?
C16 C15 N1 C12 -61.7(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
C10 H10A F4 0.97 2.54 3.413(3) 149.4 1_655
C11 H11A O4 0.97 2.56 3.495(3) 161.2 .
C13 H13A O2 0.97 2.43 3.392(3) 174.1 1_545
C15 H15A O2 0.97 2.57 3.468(3) 153.5 1_545
C16 H16B F1 0.97 2.57 3.231(3) 125.4 2_765
N1 D1 O3 0.92(2) 1.82(2) 2.722(2) 167(2) 1_655
O1 D1A O3 0.96(3) 2.66(3) 3.308(2) 125(2) 1_565
O1 D1A O4 0.96(3) 1.59(3) 2.5542(18) 176(3) 1_565

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_8-H
_database_code_depnum_ccdc_archive 'CCDC 1911924'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C4 H12 N'
_chemical_formula_sum            'C12 H13 F4 N O4'
_chemical_formula_weight         311.23

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      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                   9.5943(8)
_cell_length_b                   20.769(2)
_cell_length_c                   6.8719(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.423(8)
_cell_angle_gamma                90
_cell_volume                     1365.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6627
_cell_measurement_theta_min      2.129
_cell_measurement_theta_max      29.523

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             640.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6627
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.129
_diffrn_reflns_theta_max         29.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3821
_reflns_number_gt                2170
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0523P)²+1.0262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3238
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1575
_refine_ls_wR_factor_gt          0.1394
_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
C1 C 1.0952(2) 0.18170(12) 0.8401(4) 0.0333(6) Uani 1 1 d . . . . .
C2 C 0.9403(2) 0.18312(12) 0.8751(3) 0.0307(5) Uani 1 1 d . . . . .
C3 C 0.8664(2) 0.12741(12) 0.9030(4) 0.0362(6) Uani 1 1 d . . . . .
C4 C 0.7239(2) 0.12842(12) 0.9276(4) 0.0357(6) Uani 1 1 d . . . . .
C5 C 0.6514(2) 0.18585(12) 0.9350(3) 0.0306(5) Uani 1 1 d . . . . .
C6 C 0.4987(2) 0.18865(13) 0.9726(4) 0.0341(6) Uani 1 1 d . . . . .
C7 C 0.7270(2) 0.24168(12) 0.9117(3) 0.0306(5) Uani 1 1 d . . . . .
C8 C 0.8669(2) 0.24013(12) 0.8771(3) 0.0296(5) Uani 1 1 d . . . . .
C9 C 0.3405(3) 0.11084(15) 0.4057(5) 0.0554(8) Uani 1 1 d . . . . .
H9A H 0.4132 0.1160 0.5106 0.066 Uiso 1 1 calc R U . . .
H9B H 0.3835 0.0959 0.2907 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2325(4) 0.06163(18) 0.4646(7) 0.0842(12) Uani 1 1 d . . . . .
H10A H 0.1797 0.0805 0.5651 0.101 Uiso 1 1 calc R U . . .
H10B H 0.1676 0.0529 0.3524 0.101 Uiso 1 1 calc R U . . .
C11 C 0.2927(6) 0.0003(2) 0.5373(9) 0.1114(16) Uani 1 1 d . . . . .
H11A H 0.3598 0.0088 0.6472 0.134 Uiso 1 1 calc R U . . .
H11B H 0.3424 -0.0197 0.4354 0.134 Uiso 1 1 calc R U . . .
C12 C 0.1852(6) -0.0451(2) 0.5993(7) 0.1146(18) Uani 1 1 d . . . . .
H12A H 0.1440 -0.0281 0.7113 0.172 Uiso 1 1 calc R U . . .
H12B H 0.2279 -0.0859 0.6319 0.172 Uiso 1 1 calc R U . . .
H12C H 0.1140 -0.0508 0.4946 0.172 Uiso 1 1 calc R U . . .
F1 F 0.92995(15) 0.06971(7) 0.9022(3) 0.0568(5) Uani 1 1 d . . . . .
F2 F 0.65993(15) 0.07189(8) 0.9509(3) 0.0592(5) Uani 1 1 d . . . . .
F3 F 0.66513(15) 0.29958(7) 0.9170(2) 0.0452(4) Uani 1 1 d . . . . .
F4 F 0.93096(15) 0.29667(7) 0.8492(2) 0.0438(4) Uani 1 1 d . . . . .
H3 H 0.323(4) 0.1487(18) 0.915(5) 0.088(12) Uiso 1 1 d . . . . .
N1 N 0.2696(2) 0.17283(11) 0.3643(3) 0.0458(6) Uani 1 1 d . . . . .
H1A H 0.2065 0.1683 0.2635 0.069 Uiso 1 1 calc R U . . .
H1B H 0.3323 0.2023 0.3358 0.069 Uiso 1 1 calc R U . . .
H1C H 0.2274 0.1854 0.4687 0.069 Uiso 1 1 calc R U . . .
O1 O 1.13320(18) 0.21171(10) 0.6992(3) 0.0462(5) Uani 1 1 d . . . . .
O2 O 1.17178(16) 0.14874(9) 0.9604(3) 0.0419(5) Uani 1 1 d . . . . .
O3 O 0.42438(17) 0.14329(10) 0.8883(3) 0.0471(5) Uani 1 1 d . . . . .
O4 O 0.45551(18) 0.23064(10) 1.0747(3) 0.0468(5) 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 1.230(3) . ?
C1 O2 1.264(3) . ?
C1 C2 1.524(3) . ?
C2 C8 1.378(3) . ?
C2 C3 1.378(3) . ?
C3 F1 1.345(3) . ?
C3 C4 1.390(3) . ?
C4 F2 1.340(3) . ?
C4 C5 1.383(3) . ?
C5 C7 1.383(3) . ?
C5 C6 1.509(3) . ?
C6 O4 1.212(3) . ?
C6 O3 1.292(3) . ?
C7 F3 1.343(3) . ?
C7 C8 1.382(3) . ?
C8 F4 1.346(3) . ?
C9 N1 1.473(4) . ?
C9 C10 1.532(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.471(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.485(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O3 H3 1.01(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 126.6(2) . . ?
O1 C1 C2 117.8(2) . . ?
O2 C1 C2 115.6(2) . . ?
C8 C2 C3 116.84(19) . . ?
C8 C2 C1 121.5(2) . . ?
C3 C2 C1 121.6(2) . . ?
F1 C3 C2 120.6(2) . . ?
F1 C3 C4 117.7(2) . . ?
C2 C3 C4 121.7(2) . . ?
F2 C4 C5 120.99(19) . . ?
F2 C4 C3 117.7(2) . . ?
C5 C4 C3 121.3(2) . . ?
C7 C5 C4 116.70(19) . . ?
C7 C5 C6 120.8(2) . . ?
C4 C5 C6 122.5(2) . . ?
O4 C6 O3 125.7(2) . . ?
O4 C6 C5 120.4(2) . . ?
O3 C6 C5 113.9(2) . . ?
F3 C7 C8 117.6(2) . . ?
F3 C7 C5 120.75(19) . . ?
C8 C7 C5 121.7(2) . . ?
F4 C8 C2 120.62(19) . . ?
F4 C8 C7 117.7(2) . . ?
C2 C8 C7 121.7(2) . . ?
N1 C9 C10 108.8(3) . . ?
N1 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
N1 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C11 C10 C9 114.3(4) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 112.6(5) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 O3 H3 110(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
O1 C1 C2 C8 -49.6(3) . . . . ?
O2 C1 C2 C8 131.0(2) . . . . ?
O1 C1 C2 C3 129.3(3) . . . . ?
O2 C1 C2 C3 -50.1(3) . . . . ?
C8 C2 C3 F1 179.7(2) . . . . ?
C1 C2 C3 F1 0.7(4) . . . . ?
C8 C2 C3 C4 1.5(4) . . . . ?
C1 C2 C3 C4 -177.5(2) . . . . ?
F1 C3 C4 F2 0.7(4) . . . . ?
C2 C3 C4 F2 179.0(2) . . . . ?
F1 C3 C4 C5 178.4(2) . . . . ?
C2 C3 C4 C5 -3.4(4) . . . . ?
F2 C4 C5 C7 179.2(2) . . . . ?
C3 C4 C5 C7 1.7(4) . . . . ?
F2 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C5 C6 -176.5(2) . . . . ?
C7 C5 C6 O4 -37.2(3) . . . . ?
C4 C5 C6 O4 140.9(3) . . . . ?
C7 C5 C6 O3 143.1(2) . . . . ?
C4 C5 C6 O3 -38.8(3) . . . . ?
C4 C5 C7 F3 -180.0(2) . . . . ?
C6 C5 C7 F3 -1.7(3) . . . . ?
C4 C5 C7 C8 1.7(3) . . . . ?
C6 C5 C7 C8 180.0(2) . . . . ?
C3 C2 C8 F4 -179.4(2) . . . . ?
C1 C2 C8 F4 -0.4(3) . . . . ?
C3 C2 C8 C7 2.0(3) . . . . ?
C1 C2 C8 C7 -179.0(2) . . . . ?
F3 C7 C8 F4 -0.7(3) . . . . ?
C5 C7 C8 F4 177.7(2) . . . . ?
F3 C7 C8 C2 178.0(2) . . . . ?
C5 C7 C8 C2 -3.7(4) . . . . ?
N1 C9 C10 C11 -171.6(4) . . . . ?
C9 C10 C11 C12 178.0(4) . . . . ?

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
O3 H3 O2 1.01(4) 1.50(4) 2.513(2) 173(4) 1_455
N1 H1C O1 0.89 1.96 2.851(3) 179.1 1_455
N1 H1B O4 0.89 2.39 2.982(3) 123.7 4_565
N1 H1B O4 0.89 2.30 3.021(3) 138.1 1_554
N1 H1A O2 0.89 2.12 2.904(3) 146.1 1_454
C9 H9A O3 0.97 2.65 3.419(4) 136.4 .

_refine_diff_density_max         0.523
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_5-H
_database_code_depnum_ccdc_archive 'CCDC 1911918'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C6 H8 N'
_chemical_formula_sum            'C14 H9 F4 N O4'
_chemical_formula_weight         331.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.2846(5)
_cell_length_b                   9.7080(6)
_cell_length_c                   19.3450(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1368.06(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10472
_cell_measurement_theta_min      2.106
_cell_measurement_theta_max      29.509

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             672.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10472
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.106
_diffrn_reflns_theta_max         29.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3811
_reflns_number_gt                2589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_max     0.821
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0408P)²+0.1483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 824 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3368
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.2522(3) 0.7072(3) -0.03247(13) 0.0306(6) Uani 1 1 d . . . . .
C2 C 0.2770(3) 0.8579(2) -0.01558(12) 0.0289(5) Uani 1 1 d . . . . .
C3 C 0.3442(4) 0.9500(3) -0.06435(12) 0.0315(6) Uani 1 1 d . . . . .
C4 C 0.3709(4) 1.0866(3) -0.04893(12) 0.0318(6) Uani 1 1 d . . . . .
C5 C 0.3307(3) 1.1413(2) 0.01556(13) 0.0297(6) Uani 1 1 d . . . . .
C6 C 0.3569(4) 1.2937(3) 0.03123(13) 0.0317(6) Uani 1 1 d . . . . .
C7 C 0.2619(4) 1.0493(3) 0.06353(12) 0.0313(6) Uani 1 1 d . . . . .
C8 C 0.2371(4) 0.9122(3) 0.04881(12) 0.0311(6) Uani 1 1 d . . . . .
C9 C 0.5250(6) 0.2131(4) 0.2423(2) 0.0765(12) Uani 1 1 d . . . . .
H9 H 0.4321 0.2788 0.2420 0.092 Uiso 1 1 calc R U . . .
C10 C 0.5761(5) 0.1537(4) 0.30292(19) 0.0660(10) Uani 1 1 d . . . . .
H10 H 0.5207 0.1790 0.3443 0.079 Uiso 1 1 calc R U . . .
C11 C 0.7110(4) 0.0557(3) 0.30163(14) 0.0457(7) Uani 1 1 d . . . . .
H11 H 0.7461 0.0134 0.3427 0.055 Uiso 1 1 calc R U . . .
C12 C 0.7958(4) 0.0184(3) 0.24086(12) 0.0391(7) Uani 1 1 d . . . . .
C13 C 0.7403(5) 0.0833(3) 0.18145(14) 0.0487(8) Uani 1 1 d . . . . .
H13 H 0.7959 0.0613 0.1396 0.058 Uiso 1 1 calc R U . . .
C14 C 0.9416(5) -0.0911(4) 0.23844(16) 0.0645(10) Uani 1 1 d . . . . .
H14A H 0.9262 -0.1457 0.1975 0.097 Uiso 1 1 calc R U . . .
H14B H 0.9313 -0.1490 0.2785 0.097 Uiso 1 1 calc R U . . .
H14C H 1.0605 -0.0485 0.2378 0.097 Uiso 1 1 calc R U . . .
F1 F 0.3888(3) 0.90522(16) -0.12795(7) 0.0500(5) Uani 1 1 d . . . . .
F2 F 0.4417(3) 1.16848(16) -0.09840(8) 0.0503(5) Uani 1 1 d . . . . .
F3 F 0.1643(3) 0.83106(17) 0.09805(8) 0.0510(5) Uani 1 1 d . . . . .
F4 F 0.2142(3) 1.09457(16) 0.12727(7) 0.0493(5) Uani 1 1 d . . . . .
H1 H 0.562(6) 0.225(5) 0.140(2) 0.112(15) Uiso 1 1 d . . . . .
H2 H 0.296(6) 0.527(4) 0.0040(16) 0.087(12) Uiso 1 1 d . . . . .
N1 N 0.6074(5) 0.1777(3) 0.18306(16) 0.0615(8) Uani 1 1 d . . . . .
O1 O 0.1832(3) 0.6702(2) -0.08595(9) 0.0486(5) Uani 1 1 d . . . . .
O2 O 0.3146(3) 0.62749(19) 0.01628(10) 0.0428(5) Uani 1 1 d . . . . .
O3 O 0.2884(3) 1.37470(18) -0.01218(9) 0.0427(5) Uani 1 1 d . . . . .
O4 O 0.4410(3) 1.3253(2) 0.08467(9) 0.0441(5) 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 1.205(3) . ?
C1 O2 1.302(3) . ?
C1 C2 1.510(3) . ?
C2 C8 1.384(3) . ?
C2 C3 1.389(3) . ?
C3 F1 1.345(3) . ?
C3 C4 1.373(4) . ?
C4 F2 1.346(3) . ?
C4 C5 1.387(3) . ?
C5 C7 1.382(3) . ?
C5 C6 1.522(3) . ?
C6 O4 1.240(3) . ?
C6 O3 1.254(3) . ?
C7 F4 1.354(3) . ?
C7 C8 1.373(4) . ?
C8 F3 1.345(3) . ?
C9 N1 1.339(5) . ?
C9 C10 1.359(5) . ?
C10 C11 1.368(5) . ?
C11 C12 1.377(4) . ?
C12 C13 1.372(4) . ?
C12 C14 1.503(5) . ?
C13 N1 1.333(5) . ?

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 O2 126.2(2) . . ?
O1 C1 C2 121.7(2) . . ?
O2 C1 C2 112.2(2) . . ?
C8 C2 C3 116.1(2) . . ?
C8 C2 C1 122.6(2) . . ?
C3 C2 C1 121.3(2) . . ?
F1 C3 C4 118.5(2) . . ?
F1 C3 C2 119.9(2) . . ?
C4 C3 C2 121.6(2) . . ?
F2 C4 C3 118.0(2) . . ?
F2 C4 C5 119.6(2) . . ?
C3 C4 C5 122.3(2) . . ?
C7 C5 C4 115.7(2) . . ?
C7 C5 C6 122.7(2) . . ?
C4 C5 C6 121.7(2) . . ?
O4 C6 O3 126.9(2) . . ?
O4 C6 C5 117.9(2) . . ?
O3 C6 C5 115.2(2) . . ?
F4 C7 C8 118.0(2) . . ?
F4 C7 C5 119.7(2) . . ?
C8 C7 C5 122.3(2) . . ?
F3 C8 C7 118.2(2) . . ?
F3 C8 C2 119.8(2) . . ?
C7 C8 C2 121.9(2) . . ?
N1 C9 C10 120.4(4) . . ?
C9 C10 C11 118.5(3) . . ?
C10 C11 C12 121.4(3) . . ?
C13 C12 C11 117.5(3) . . ?
C13 C12 C14 120.5(3) . . ?
C11 C12 C14 122.0(3) . . ?
N1 C13 C12 120.7(3) . . ?
C13 N1 C9 121.5(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
O1 C1 C2 C8 136.0(3) . . . . ?
O2 C1 C2 C8 -44.6(3) . . . . ?
O1 C1 C2 C3 -44.7(4) . . . . ?
O2 C1 C2 C3 134.6(2) . . . . ?
C8 C2 C3 F1 179.1(2) . . . . ?
C1 C2 C3 F1 -0.2(4) . . . . ?
C8 C2 C3 C4 0.7(4) . . . . ?
C1 C2 C3 C4 -178.6(2) . . . . ?
F1 C3 C4 F2 -0.4(4) . . . . ?
C2 C3 C4 F2 178.0(2) . . . . ?
F1 C3 C4 C5 -179.3(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
F2 C4 C5 C7 -178.8(2) . . . . ?
C3 C4 C5 C7 0.1(4) . . . . ?
F2 C4 C5 C6 2.6(4) . . . . ?
C3 C4 C5 C6 -178.5(2) . . . . ?
C7 C5 C6 O4 50.5(3) . . . . ?
C4 C5 C6 O4 -131.0(3) . . . . ?
C7 C5 C6 O3 -129.2(3) . . . . ?
C4 C5 C6 O3 49.3(3) . . . . ?
C4 C5 C7 F4 -178.3(2) . . . . ?
C6 C5 C7 F4 0.3(4) . . . . ?
C4 C5 C7 C8 0.9(4) . . . . ?
C6 C5 C7 C8 179.4(2) . . . . ?
F4 C7 C8 F3 1.0(4) . . . . ?
C5 C7 C8 F3 -178.1(2) . . . . ?
F4 C7 C8 C2 178.1(2) . . . . ?
C5 C7 C8 C2 -1.0(4) . . . . ?
C3 C2 C8 F3 177.2(2) . . . . ?
C1 C2 C8 F3 -3.5(4) . . . . ?
C3 C2 C8 C7 0.2(4) . . . . ?
C1 C2 C8 C7 179.5(2) . . . . ?
N1 C9 C10 C11 -1.1(6) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C10 C11 C12 C14 -178.8(3) . . . . ?
C11 C12 C13 N1 -0.8(5) . . . . ?
C14 C12 C13 N1 178.1(3) . . . . ?
C12 C13 N1 C9 0.6(5) . . . . ?
C10 C9 N1 C13 0.4(6) . . . . ?

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
O2 H2 O3 1.01(4) 1.51(4) 2.522(2) 174(4) 1_545
N1 H1 O4 1.00(4) 1.70(4) 2.673(3) 163(4) 1_545
C13 H13 O3 0.93 2.54 3.318(3) 141.1 4_565
C13 H13 O1 0.93 2.61 3.105(4) 114.0 4
C10 H10 O1 0.93 2.48 3.334(4) 152.0 2_565

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_11-H
_database_code_depnum_ccdc_archive 'CCDC 1911930'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C3 H5 N2'
_chemical_formula_sum            'C11 H6 F4 N2 O4'
_chemical_formula_weight         306.18

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   9.6878(5)
_cell_length_b                   7.2046(5)
_cell_length_c                   17.3573(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1211.48(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6714
_cell_measurement_theta_min      2.347
_cell_measurement_theta_max      29.637

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_F_000             616.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.167
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6714
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         29.637
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             3408
_reflns_number_gt                2259
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.711
_reflns_Friedel_fraction_full    0.894

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2770
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.7646(3) 0.4441(4) 0.91283(17) 0.0257(7) Uani 1 1 d . . . . .
C2 C 0.6117(3) 0.4724(4) 0.92871(19) 0.0254(6) Uani 1 1 d . . . . .
C3 C 0.5241(3) 0.5446(4) 0.87327(17) 0.0269(7) Uani 1 1 d . . . . .
C4 C 0.3864(3) 0.5732(4) 0.88792(19) 0.0280(7) Uani 1 1 d . . . . .
C5 C 0.3284(3) 0.5304(4) 0.95873(19) 0.0267(7) Uani 1 1 d . . . . .
C6 C 0.1784(3) 0.5591(4) 0.97595(19) 0.0292(7) Uani 1 1 d . . . . .
C7 C 0.4158(3) 0.4576(4) 1.01361(19) 0.0269(7) Uani 1 1 d . . . . .
C8 C 0.5535(3) 0.4290(4) 0.99857(19) 0.0270(7) Uani 1 1 d . . . . .
C9 C 0.9534(4) 0.4953(6) 0.1660(2) 0.0485(9) Uani 1 1 d . . . . .
H9 H 1.0162 0.4089 0.1471 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7884(4) 0.6968(6) 0.1706(2) 0.0486(9) Uani 1 1 d . . . . .
H10 H 0.7165 0.7752 0.1563 0.058 Uiso 1 1 calc R U . . .
C11 C 0.9414(4) 0.5505(6) 0.2383(2) 0.0498(10) Uani 1 1 d . . . . .
H11 H 0.9940 0.5105 0.2799 0.060 Uiso 1 1 calc R U . . .
F1 F 0.5723(2) 0.5916(3) 0.80387(11) 0.0419(5) Uani 1 1 d . . . . .
F2 F 0.30849(19) 0.6499(3) 0.83278(11) 0.0429(5) Uani 1 1 d . . . . .
F3 F 0.63035(18) 0.3520(3) 1.05435(11) 0.0424(5) Uani 1 1 d . . . . .
F4 F 0.36642(19) 0.4082(3) 1.08285(11) 0.0437(5) Uani 1 1 d . . . . .
H1 H 0.841(5) 0.581(7) 0.078(3) 0.074(17) Uiso 1 1 d . . . . .
H2 H 0.803(5) 0.738(6) 0.283(3) 0.067(14) Uiso 1 1 d . . . . .
H3 H 0.022(5) 0.497(8) 0.935(3) 0.052(12) Uiso 1 1 d . . . . .
N1 N 0.8571(3) 0.5879(5) 0.1248(2) 0.0484(8) Uani 1 1 d . . . . .
N2 N 0.8375(3) 0.6770(5) 0.24007(18) 0.0421(8) Uani 1 1 d . . . . .
O1 O 0.7985(2) 0.3640(4) 0.85328(13) 0.0385(6) Uani 1 1 d . . . . .
O2 O 0.8453(2) 0.5085(4) 0.96308(13) 0.0340(6) Uani 1 1 d . . . . .
O3 O 0.0975(2) 0.4850(4) 0.92439(15) 0.0386(6) Uani 1 1 d . . . . .
O4 O 0.1405(2) 0.6412(4) 1.03220(14) 0.0426(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
C1 O1 1.229(4) . ?
C1 O2 1.260(4) . ?
C1 C2 1.520(4) . ?
C2 C8 1.373(5) . ?
C2 C3 1.384(4) . ?
C3 F1 1.336(3) . ?
C3 C4 1.374(4) . ?
C4 F2 1.338(4) . ?
C4 C5 1.386(5) . ?
C5 C7 1.378(5) . ?
C5 C6 1.498(4) . ?
C6 O4 1.199(4) . ?
C6 O3 1.304(4) . ?
C7 F4 1.342(4) . ?
C7 C8 1.375(4) . ?
C8 F3 1.342(4) . ?
C9 C11 1.321(6) . ?
C9 N1 1.351(5) . ?
C10 N1 1.301(5) . ?
C10 N2 1.304(5) . ?
C11 N2 1.358(5) . ?

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 O2 126.1(3) . . ?
O1 C1 C2 118.5(3) . . ?
O2 C1 C2 115.5(3) . . ?
C8 C2 C3 116.6(3) . . ?
C8 C2 C1 122.0(3) . . ?
C3 C2 C1 121.4(3) . . ?
F1 C3 C4 117.9(3) . . ?
F1 C3 C2 120.5(3) . . ?
C4 C3 C2 121.5(3) . . ?
F2 C4 C3 118.5(3) . . ?
F2 C4 C5 119.8(3) . . ?
C3 C4 C5 121.6(3) . . ?
C7 C5 C4 116.6(3) . . ?
C7 C5 C6 120.7(3) . . ?
C4 C5 C6 122.7(3) . . ?
O4 C6 O3 125.2(3) . . ?
O4 C6 C5 121.9(3) . . ?
O3 C6 C5 112.9(3) . . ?
F4 C7 C8 118.4(3) . . ?
F4 C7 C5 120.1(3) . . ?
C8 C7 C5 121.5(3) . . ?
F3 C8 C2 120.2(3) . . ?
F3 C8 C7 117.6(3) . . ?
C2 C8 C7 122.2(3) . . ?
C11 C9 N1 107.1(3) . . ?
N1 C10 N2 108.2(4) . . ?
C9 C11 N2 106.8(4) . . ?
C10 N1 C9 109.1(3) . . ?
C10 N2 C11 108.8(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
O1 C1 C2 C8 131.5(3) . . . . ?
O2 C1 C2 C8 -49.2(4) . . . . ?
O1 C1 C2 C3 -49.0(4) . . . . ?
O2 C1 C2 C3 130.4(3) . . . . ?
C8 C2 C3 F1 179.6(3) . . . . ?
C1 C2 C3 F1 0.0(4) . . . . ?
C8 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C4 -178.9(3) . . . . ?
F1 C3 C4 F2 -1.3(4) . . . . ?
C2 C3 C4 F2 177.5(3) . . . . ?
F1 C3 C4 C5 -179.2(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
F2 C4 C5 C7 -177.9(3) . . . . ?
C3 C4 C5 C7 -0.1(4) . . . . ?
F2 C4 C5 C6 2.6(5) . . . . ?
C3 C4 C5 C6 -179.6(3) . . . . ?
C7 C5 C6 O4 51.3(5) . . . . ?
C4 C5 C6 O4 -129.2(4) . . . . ?
C7 C5 C6 O3 -128.1(3) . . . . ?
C4 C5 C6 O3 51.4(4) . . . . ?
C4 C5 C7 F4 -178.2(3) . . . . ?
C6 C5 C7 F4 1.3(5) . . . . ?
C4 C5 C7 C8 0.0(5) . . . . ?
C6 C5 C7 C8 179.5(3) . . . . ?
C3 C2 C8 F3 177.5(3) . . . . ?
C1 C2 C8 F3 -2.9(5) . . . . ?
C3 C2 C8 C7 -0.8(5) . . . . ?
C1 C2 C8 C7 178.8(3) . . . . ?
F4 C7 C8 F3 0.4(5) . . . . ?
C5 C7 C8 F3 -177.9(3) . . . . ?
F4 C7 C8 C2 178.7(3) . . . . ?
C5 C7 C8 C2 0.5(5) . . . . ?
N1 C9 C11 N2 -0.1(4) . . . . ?
N2 C10 N1 C9 0.0(5) . . . . ?
C11 C9 N1 C10 0.0(4) . . . . ?
N1 C10 N2 C11 -0.1(5) . . . . ?
C9 C11 N2 C10 0.1(5) . . . . ?

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
O3 H3 O2 0.76(5) 1.78(5) 2.539(3) 175(6) 1_455
N2 H2 O1 0.92(5) 1.81(5) 2.723(4) 168(4) 4_654
N1 H1 O2 0.83(5) 2.06(5) 2.867(4) 164(5) 1_554
C11 H11 O3 0.93 2.66 3.263(5) 123.1 2_664
C11 H11 O1 0.93 2.55 3.273(5) 135.4 2_764
C10 H10 O4 0.93 2.36 3.032(5) 129.3 3_564

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_10-H
_database_code_depnum_ccdc_archive 'CCDC 1911928'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C4 H12 N O'
_chemical_formula_sum            'C12 H13 F4 N O5'
_chemical_formula_weight         327.23

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                   9.6026(9)
_cell_length_b                   17.6586(15)
_cell_length_c                   9.0164(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.170(11)
_cell_angle_gamma                90
_cell_volume                     1435.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7375
_cell_measurement_theta_min      2.259
_cell_measurement_theta_max      29.513

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7375
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.259
_diffrn_reflns_theta_max         29.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4001
_reflns_number_gt                2195
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0431P)²+0.4762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3397
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 -0.1186(2) 0.74254(13) 1.0312(2) 0.0419(5) Uani 1 1 d . . . . .
C2 C 0.02330(19) 0.72943(12) 0.9982(2) 0.0376(5) Uani 1 1 d . . . . .
C3 C 0.0824(2) 0.65877(12) 0.9978(2) 0.0421(5) Uani 1 1 d . . . . .
C4 C 0.2091(2) 0.64795(12) 0.9619(3) 0.0448(5) Uani 1 1 d . . . . .
C5 C 0.2840(2) 0.70770(12) 0.9259(2) 0.0386(5) Uani 1 1 d . . . . .
C6 C 0.2247(2) 0.77864(12) 0.9270(2) 0.0413(5) Uani 1 1 d . . . . .
C7 C 0.0981(2) 0.78926(12) 0.9626(3) 0.0427(5) Uani 1 1 d . . . . .
C8 C 0.4241(2) 0.69612(13) 0.8871(3) 0.0439(5) Uani 1 1 d . . . . .
C9 C 0.6419(5) 0.5766(2) 0.2161(4) 0.1204(14) Uani 1 1 d . . . . .
H9A H 0.7338 0.5796 0.1962 0.181 Uiso 1 1 calc R U . . .
H9B H 0.5822 0.6201 0.1717 0.181 Uiso 1 1 calc R U . . .
H9C H 0.5898 0.5315 0.1684 0.181 Uiso 1 1 calc R U . . .
C10 C 0.7602(3) 0.51360(17) 0.4549(3) 0.0707(7) Uani 1 1 d . . . . .
H10A H 0.8420 0.5074 0.4160 0.085 Uiso 1 1 calc R U . . .
H10B H 0.7025 0.4672 0.4339 0.085 Uiso 1 1 calc R U . . .
C11 C 0.8189(3) 0.52853(15) 0.6281(3) 0.0614(7) Uani 1 1 d . . . . .
H11A H 0.8896 0.5699 0.6484 0.074 Uiso 1 1 calc R U . . .
H11B H 0.8723 0.4840 0.6811 0.074 Uiso 1 1 calc R U . . .
C12 C 0.7037(3) 0.54805(15) 0.6994(3) 0.0608(7) Uani 1 1 d . . . . .
H12A H 0.6261 0.5100 0.6692 0.073 Uiso 1 1 calc R U . . .
H12B H 0.7486 0.5475 0.8136 0.073 Uiso 1 1 calc R U . . .
F1 F 0.28923(14) 0.83937(8) 0.88769(18) 0.0632(4) Uani 1 1 d . . . . .
F2 F 0.04369(15) 0.85951(8) 0.9550(2) 0.0717(5) Uani 1 1 d . . . . .
F3 F 0.01626(14) 0.59784(8) 1.03424(19) 0.0685(4) Uani 1 1 d . . . . .
F4 F 0.26064(15) 0.57709(8) 0.9665(2) 0.0750(5) Uani 1 1 d . . . . .
H3 H -0.337(3) 0.7215(16) 0.952(3) 0.096(9) Uiso 1 1 d . . . . .
N1 N 0.63717(19) 0.62378(10) 0.6474(2) 0.0490(5) Uani 1 1 d . . . . .
H1A H 0.7070 0.6592 0.6811 0.073 Uiso 1 1 calc R U . . .
H1B H 0.5660 0.6325 0.6875 0.073 Uiso 1 1 calc R U . . .
H1C H 0.5987 0.6250 0.5424 0.073 Uiso 1 1 calc R U . . .
O1 O 0.42237(17) 0.64998(11) 0.7861(2) 0.0663(5) Uani 1 1 d . . . . .
O2 O 0.53193(16) 0.73649(10) 0.9673(2) 0.0623(5) Uani 1 1 d . . . . .
O3 O -0.22979(16) 0.70628(11) 0.9367(2) 0.0660(5) Uani 1 1 d . . . . .
O4 O -0.12063(16) 0.78350(10) 1.13632(19) 0.0587(5) Uani 1 1 d . . . . .
O5 O 0.6707(2) 0.57449(12) 0.3771(2) 0.0884(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
C1 O4 1.198(2) . ?
C1 O3 1.284(3) . ?
C1 C2 1.509(3) . ?
C2 C3 1.371(3) . ?
C2 C7 1.377(3) . ?
C3 F3 1.346(2) . ?
C3 C4 1.376(3) . ?
C4 F4 1.341(2) . ?
C4 C5 1.378(3) . ?
C5 C6 1.377(3) . ?
C5 C8 1.516(3) . ?
C6 F1 1.345(2) . ?
C6 C7 1.373(3) . ?
C7 F2 1.339(2) . ?
C8 O1 1.218(3) . ?
C8 O2 1.260(3) . ?
C9 O5 1.382(3) . ?
C10 O5 1.404(3) . ?
C10 C11 1.490(4) . ?
C11 C12 1.499(3) . ?
C12 N1 1.487(3) . ?

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
O4 C1 O3 126.14(18) . . ?
O4 C1 C2 120.69(18) . . ?
O3 C1 C2 113.17(18) . . ?
C3 C2 C7 116.61(17) . . ?
C3 C2 C1 122.86(18) . . ?
C7 C2 C1 120.51(19) . . ?
F3 C3 C2 119.75(17) . . ?
F3 C3 C4 118.43(19) . . ?
C2 C3 C4 121.82(19) . . ?
F4 C4 C3 118.00(19) . . ?
F4 C4 C5 120.30(17) . . ?
C3 C4 C5 121.7(2) . . ?
C6 C5 C4 116.38(17) . . ?
C6 C5 C8 121.73(18) . . ?
C4 C5 C8 121.89(19) . . ?
F1 C6 C7 118.54(19) . . ?
F1 C6 C5 119.63(17) . . ?
C7 C6 C5 121.80(19) . . ?
F2 C7 C6 118.44(19) . . ?
F2 C7 C2 119.80(17) . . ?
C6 C7 C2 121.69(19) . . ?
O1 C8 O2 127.21(18) . . ?
O1 C8 C5 118.60(19) . . ?
O2 C8 C5 114.19(19) . . ?
O5 C10 C11 109.5(2) . . ?
C10 C11 C12 115.0(2) . . ?
N1 C12 C11 111.85(19) . . ?
C9 O5 C10 114.3(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
O4 C1 C2 C3 123.1(2) . . . . ?
O3 C1 C2 C3 -57.1(3) . . . . ?
O4 C1 C2 C7 -58.6(3) . . . . ?
O3 C1 C2 C7 121.1(2) . . . . ?
C7 C2 C3 F3 178.89(18) . . . . ?
C1 C2 C3 F3 -2.8(3) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C4 177.64(19) . . . . ?
F3 C3 C4 F4 -0.5(3) . . . . ?
C2 C3 C4 F4 179.04(19) . . . . ?
F3 C3 C4 C5 -178.97(19) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
F4 C4 C5 C6 -178.77(19) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
F4 C4 C5 C8 1.3(3) . . . . ?
C3 C4 C5 C8 179.70(19) . . . . ?
C4 C5 C6 F1 -177.75(18) . . . . ?
C8 C5 C6 F1 2.2(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C8 C5 C6 C7 -179.80(19) . . . . ?
F1 C6 C7 F2 0.7(3) . . . . ?
C5 C6 C7 F2 -177.36(19) . . . . ?
F1 C6 C7 C2 177.64(18) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C3 C2 C7 F2 177.50(19) . . . . ?
C1 C2 C7 F2 -0.9(3) . . . . ?
C3 C2 C7 C6 0.6(3) . . . . ?
C1 C2 C7 C6 -177.79(19) . . . . ?
C6 C5 C8 O1 -128.3(2) . . . . ?
C4 C5 C8 O1 51.6(3) . . . . ?
C6 C5 C8 O2 52.3(3) . . . . ?
C4 C5 C8 O2 -127.8(2) . . . . ?
O5 C10 C11 C12 52.7(3) . . . . ?
C10 C11 C12 N1 -69.5(3) . . . . ?
C11 C10 O5 C9 164.0(3) . . . . ?

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
C11 H11A O4 0.97 2.59 3.366(3) 136.9 4_675
O3 H3 O1 1.11(3) 2.61(3) 3.296(2) 119.2(18) 1_455
O3 H3 O2 1.11(3) 1.34(3) 2.4561(19) 177(3) 1_455
N1 H1A O3 0.89 2.32 2.874(2) 119.9 1_655
N1 H1A O4 0.89 2.10 2.874(2) 145.6 4_675
N1 H1B O1 0.89 1.91 2.795(2) 176.5 .
N1 H1C O5 0.89 2.05 2.709(3) 129.9 .

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_9-D
_database_code_depnum_ccdc_archive 'CCDC 1911927'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C5 H11 D3 N'
_chemical_formula_sum            'C13 H11 D4 F4 N O4'
_chemical_formula_weight         329.27

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      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                   9.5797(8)
_cell_length_b                   23.308(2)
_cell_length_c                   6.8151(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.216(8)
_cell_angle_gamma                90
_cell_volume                     1517.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7994
_cell_measurement_theta_min      2.132
_cell_measurement_theta_max      29.457

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             672.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7994
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.132
_diffrn_reflns_theta_max         29.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4219
_reflns_number_gt                2360
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0530P)²+0.7995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3587
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 1.0481(2) 0.19130(10) 0.2682(3) 0.0352(5) Uani 1 1 d . . . . .
C2 C 0.8932(2) 0.19329(10) 0.3040(3) 0.0340(5) Uani 1 1 d . . . . .
C3 C 0.8181(2) 0.14361(10) 0.3307(4) 0.0411(6) Uani 1 1 d . . . . .
C4 C 0.6766(2) 0.14463(10) 0.3564(4) 0.0408(6) Uani 1 1 d . . . . .
C5 C 0.6046(2) 0.19574(10) 0.3654(3) 0.0351(5) Uani 1 1 d . . . . .
C6 C 0.4517(2) 0.19797(10) 0.4034(3) 0.0371(5) Uani 1 1 d . . . . .
C7 C 0.6798(2) 0.24552(9) 0.3418(3) 0.0326(5) Uani 1 1 d . . . . .
C8 C 0.8194(2) 0.24403(9) 0.3080(3) 0.0326(5) Uani 1 1 d . . . . .
F1 F 0.88195(14) 0.09238(6) 0.3286(3) 0.0657(5) Uani 1 1 d . . . . .
F2 F 0.61211(14) 0.09423(6) 0.3789(3) 0.0666(5) Uani 1 1 d . . . . .
F3 F 0.88425(13) 0.29437(6) 0.2804(2) 0.0462(4) Uani 1 1 d . . . . .
F4 F 0.61828(13) 0.29708(6) 0.3485(2) 0.0469(4) Uani 1 1 d . . . . .
O1 O 1.12356(15) 0.16148(7) 0.3875(2) 0.0438(4) Uani 1 1 d . . . . .
O2 O 1.08606(16) 0.21830(8) 0.1266(2) 0.0482(4) Uani 1 1 d . . . . .
O3 O 0.37805(17) 0.15771(8) 0.3169(3) 0.0487(5) Uani 1 1 d . . . . .
O4 O 0.40733(15) 0.23475(8) 0.5081(3) 0.0489(5) Uani 1 1 d . . . . .
C9 C 0.2948(3) 0.12592(13) -0.1669(4) 0.0653(8) Uani 1 1 d . . . . .
H9A H 0.3741 0.1332 -0.0735 0.078 Uiso 1 1 calc R U . . .
H9B H 0.3305 0.1118 -0.2873 0.078 Uiso 1 1 calc R U . . .
C10 C 0.2055(5) 0.08166(16) -0.0866(7) 0.1017(13) Uani 1 1 d . . . . .
H10A H 0.1317 0.0715 -0.1856 0.122 Uiso 1 1 calc R U . A 1
H10B H 0.1618 0.0973 0.0257 0.122 Uiso 1 1 calc R U . A 1
N1 N 0.2193(2) 0.17983(9) -0.2082(3) 0.0479(5) Uani 1 1 d . . . . .
D1A D 0.1543 0.1745 -0.3067 0.072 Uiso 1 1 calc R U . . .
D1B D 0.2792 0.2067 -0.2417 0.072 Uiso 1 1 calc R U . . .
D1C D 0.1785 0.1910 -0.1014 0.072 Uiso 1 1 calc R U . . .
C11 C 0.2866(8) 0.0275(2) -0.0228(11) 0.163(3) Uani 0.414(11) 1 d . . P B 1
H11A H 0.2688 -0.0003 -0.1277 0.196 Uiso 0.414(11) 1 calc R U P B 1
H11B H 0.3851 0.0372 -0.0211 0.196 Uiso 0.414(11) 1 calc R U P B 1
C12 C 0.272(3) 0.0039(15) 0.119(5) 0.187(12) Uani 0.414(11) 1 d . . P B 1
H12A H 0.3692 -0.0048 0.1596 0.224 Uiso 0.414(11) 1 calc R U P B 1
H12B H 0.2346 -0.0320 0.0673 0.224 Uiso 0.414(11) 1 calc R U P B 1
C13 C 0.217(2) 0.0041(8) 0.299(3) 0.181(9) Uani 0.414(11) 1 d . . P B 1
H13A H 0.2902 -0.0033 0.4002 0.271 Uiso 0.414(11) 1 calc R U P B 1
H13B H 0.1468 -0.0252 0.3019 0.271 Uiso 0.414(11) 1 calc R U P B 1
H13C H 0.1761 0.0408 0.3214 0.271 Uiso 0.414(11) 1 calc R U P B 1
C11' C 0.2866(8) 0.0275(2) -0.0228(11) 0.163(3) Uani 0.586(11) 1 d . . P B 2
H11C H 0.3146 0.0078 -0.1391 0.196 Uiso 0.586(11) 1 calc R U P B 2
H11D H 0.3711 0.0385 0.0552 0.196 Uiso 0.586(11) 1 calc R U P B 2
C12' C 0.2049(18) -0.0136(5) 0.095(3) 0.129(5) Uani 0.586(11) 1 d . . P B 2
H12C H 0.1755 0.0060 0.2106 0.155 Uiso 0.586(11) 1 calc R U P B 2
H12D H 0.1214 -0.0255 0.0164 0.155 Uiso 0.586(11) 1 calc R U P B 2
C13' C 0.2825(14) -0.0625(4) 0.1549(17) 0.183(6) Uani 0.586(11) 1 d . . P B 2
H13D H 0.2961 -0.0861 0.0425 0.275 Uiso 0.586(11) 1 calc R U P B 2
H13E H 0.2326 -0.0839 0.2478 0.275 Uiso 0.586(11) 1 calc R U P B 2
H13F H 0.3718 -0.0510 0.2153 0.275 Uiso 0.586(11) 1 calc R U P B 2
D3 D 0.283(3) 0.1572(13) 0.341(5) 0.080(10) 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
C1 O2 1.229(3) . ?
C1 O1 1.257(3) . ?
C1 C2 1.522(3) . ?
C2 C8 1.379(3) . ?
C2 C3 1.382(3) . ?
C3 F1 1.342(3) . ?
C3 C4 1.380(3) . ?
C4 F2 1.341(3) . ?
C4 C5 1.380(3) . ?
C5 C7 1.381(3) . ?
C5 C6 1.507(3) . ?
C6 O4 1.212(3) . ?
C6 O3 1.290(3) . ?
C7 F4 1.341(2) . ?
C7 C8 1.375(3) . ?
C8 F3 1.347(2) . ?
O3 D3 0.93(3) . ?
C9 N1 1.467(4) . ?
C9 C10 1.471(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11' 1.529(7) . ?
C10 C11 1.529(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 D1A 0.8900 . ?
N1 D1B 0.8900 . ?
N1 D1C 0.8900 . ?
C11 C12 1.13(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.37(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11' C12' 1.505(16) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' C13' 1.41(2) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 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
O2 C1 O1 126.96(19) . . ?
O2 C1 C2 117.3(2) . . ?
O1 C1 C2 115.73(19) . . ?
C8 C2 C3 116.36(19) . . ?
C8 C2 C1 122.4(2) . . ?
C3 C2 C1 121.2(2) . . ?
F1 C3 C4 118.0(2) . . ?
F1 C3 C2 120.15(19) . . ?
C4 C3 C2 121.8(2) . . ?
F2 C4 C3 117.7(2) . . ?
F2 C4 C5 120.98(19) . . ?
C3 C4 C5 121.3(2) . . ?
C4 C5 C7 116.96(19) . . ?
C4 C5 C6 122.2(2) . . ?
C7 C5 C6 120.8(2) . . ?
O4 C6 O3 125.46(19) . . ?
O4 C6 C5 120.8(2) . . ?
O3 C6 C5 113.7(2) . . ?
F4 C7 C8 117.63(19) . . ?
F4 C7 C5 120.99(18) . . ?
C8 C7 C5 121.4(2) . . ?
F3 C8 C7 117.76(19) . . ?
F3 C8 C2 120.16(18) . . ?
C7 C8 C2 122.1(2) . . ?
C6 O3 D3 115.6(19) . . ?
N1 C9 C10 112.4(3) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11' 112.8(4) . . ?
C9 C10 C11 112.8(4) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C9 N1 D1A 109.5 . . ?
C9 N1 D1B 109.5 . . ?
D1A N1 D1B 109.5 . . ?
C9 N1 D1C 109.5 . . ?
D1A N1 D1C 109.5 . . ?
D1B N1 D1C 109.5 . . ?
C12 C11 C10 123.6(18) . . ?
C12 C11 H11A 106.4 . . ?
C10 C11 H11A 106.4 . . ?
C12 C11 H11B 106.4 . . ?
C10 C11 H11B 106.4 . . ?
H11A C11 H11B 106.5 . . ?
C11 C12 C13 148(3) . . ?
C11 C12 H12A 99.9 . . ?
C13 C12 H12A 99.9 . . ?
C11 C12 H12B 99.9 . . ?
C13 C12 H12B 99.9 . . ?
H12A C12 H12B 104.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12' C11' C10 113.8(9) . . ?
C12' C11' H11C 108.8 . . ?
C10 C11' H11C 108.8 . . ?
C12' C11' H11D 108.8 . . ?
C10 C11' H11D 108.8 . . ?
H11C C11' H11D 107.7 . . ?
C13' C12' C11' 112.7(13) . . ?
C13' C12' H12C 109.0 . . ?
C11' C12' H12C 109.0 . . ?
C13' C12' H12D 109.0 . . ?
C11' C12' H12D 109.0 . . ?
H12C C12' H12D 107.8 . . ?
C12' C13' H13D 109.5 . . ?
C12' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 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
O2 C1 C2 C8 -49.4(3) . . . . ?
O1 C1 C2 C8 131.1(2) . . . . ?
O2 C1 C2 C3 129.3(2) . . . . ?
O1 C1 C2 C3 -50.2(3) . . . . ?
C8 C2 C3 F1 179.9(2) . . . . ?
C1 C2 C3 F1 1.1(3) . . . . ?
C8 C2 C3 C4 1.1(3) . . . . ?
C1 C2 C3 C4 -177.7(2) . . . . ?
F1 C3 C4 F2 0.4(4) . . . . ?
C2 C3 C4 F2 179.3(2) . . . . ?
F1 C3 C4 C5 178.2(2) . . . . ?
C2 C3 C4 C5 -3.0(4) . . . . ?
F2 C4 C5 C7 179.6(2) . . . . ?
C3 C4 C5 C7 1.9(3) . . . . ?
F2 C4 C5 C6 0.8(4) . . . . ?
C3 C4 C5 C6 -176.9(2) . . . . ?
C4 C5 C6 O4 140.6(2) . . . . ?
C7 C5 C6 O4 -38.1(3) . . . . ?
C4 C5 C6 O3 -38.8(3) . . . . ?
C7 C5 C6 O3 142.5(2) . . . . ?
C4 C5 C7 F4 180.00(19) . . . . ?
C6 C5 C7 F4 -1.2(3) . . . . ?
C4 C5 C7 C8 0.9(3) . . . . ?
C6 C5 C7 C8 179.73(19) . . . . ?
F4 C7 C8 F3 -1.1(3) . . . . ?
C5 C7 C8 F3 177.95(18) . . . . ?
F4 C7 C8 C2 178.10(18) . . . . ?
C5 C7 C8 C2 -2.8(3) . . . . ?
C3 C2 C8 F3 -179.04(19) . . . . ?
C1 C2 C8 F3 -0.3(3) . . . . ?
C3 C2 C8 C7 1.7(3) . . . . ?
C1 C2 C8 C7 -179.52(19) . . . . ?
N1 C9 C10 C11' -174.0(4) . . . . ?
N1 C9 C10 C11 -174.0(4) . . . . ?
C9 C10 C11 C12 136(2) . . . . ?
C10 C11 C12 C13 -12(7) . . . . ?
C9 C10 C11' C12' 168.7(8) . . . . ?
C10 C11' C12' C13' -178.9(10) . . . . ?

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
O3 D3 O1 0.93(3) 1.59(3) 2.521(2) 176(3) 1_455
N1 D1C O2 0.89 1.95 2.841(3) 177.6 1_455
N1 D1B O4 0.89 2.44 2.999(3) 121.0 4_565
N1 D1B O4 0.89 2.27 3.022(3) 142.2 1_554
N1 D1A O1 0.89 2.11 2.871(3) 143.7 1_454

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_9-H
_database_code_depnum_ccdc_archive 'CCDC 1911926'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C5 H14 N'
_chemical_formula_sum            'C13 H15 F4 N O4'
_chemical_formula_weight         325.26

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      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                   9.5893(9)
_cell_length_b                   23.360(3)
_cell_length_c                   6.8268(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.249(8)
_cell_angle_gamma                90
_cell_volume                     1525.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7903
_cell_measurement_theta_min      2.130
_cell_measurement_theta_max      29.338

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             672.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7903
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.130
_diffrn_reflns_theta_max         29.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4197
_reflns_number_gt                2258
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0528P)²+0.7573P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3605
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 1.0485(2) 0.19791(11) 0.0961(3) 0.0380(6) Uani 1 1 d . . . . .
C2 C 0.8957(2) 0.19575(11) 0.1351(3) 0.0354(5) Uani 1 1 d . . . . .
C3 C 0.8200(2) 0.24539(10) 0.1574(3) 0.0342(5) Uani 1 1 d . . . . .
C4 C 0.6802(2) 0.24414(10) 0.1923(3) 0.0337(5) Uani 1 1 d . . . . .
C5 C 0.6069(2) 0.19336(11) 0.1956(3) 0.0343(5) Uani 1 1 d . . . . .
C6 C 0.4519(2) 0.19150(11) 0.2319(3) 0.0364(5) Uani 1 1 d . . . . .
C7 C 0.6816(2) 0.14369(11) 0.1691(4) 0.0417(6) Uani 1 1 d . . . . .
C8 C 0.8234(2) 0.14484(11) 0.1435(4) 0.0420(6) Uani 1 1 d . . . . .
C9 C 0.2050(3) 0.12558(14) 0.6670(4) 0.0672(8) Uani 1 1 d . . . . .
H9A H 0.1251 0.1325 0.5743 0.081 Uiso 1 1 calc R U . . .
H9B H 0.1700 0.1116 0.7878 0.081 Uiso 1 1 calc R U . . .
C10 C 0.2942(5) 0.08122(17) 0.5865(7) 0.1066(14) Uani 1 1 d . . . . .
H10A H 0.3681 0.0712 0.6852 0.128 Uiso 1 1 calc R U . A 1
H10B H 0.3376 0.0968 0.4743 0.128 Uiso 1 1 calc R U . A 1
C11 C 0.2145(9) 0.0274(2) 0.5236(12) 0.176(3) Uani 0.396(12) 1 d . . P B 1
H11A H 0.2378 -0.0006 0.6256 0.212 Uiso 0.396(12) 1 calc R U P B 1
H11B H 0.1165 0.0365 0.5320 0.212 Uiso 0.396(12) 1 calc R U P B 1
C12 C 0.221(2) 0.0041(16) 0.381(5) 0.183(12) Uani 0.396(12) 1 d . . P B 1
H12A H 0.1222 0.0010 0.3381 0.220 Uiso 0.396(12) 1 calc R U P B 1
H12B H 0.2460 -0.0340 0.4281 0.220 Uiso 0.396(12) 1 calc R U P B 1
C13 C 0.281(2) 0.0043(8) 0.197(3) 0.181(9) Uani 0.396(12) 1 d . . P B 1
H13A H 0.2780 0.0423 0.1439 0.271 Uiso 0.396(12) 1 calc R U P B 1
H13B H 0.2301 -0.0212 0.1082 0.271 Uiso 0.396(12) 1 calc R U P B 1
H13C H 0.3768 -0.0081 0.2155 0.271 Uiso 0.396(12) 1 calc R U P B 1
C11' C 0.2145(9) 0.0274(2) 0.5236(12) 0.176(3) Uani 0.604(12) 1 d . . P B 2
H11C H 0.1873 0.0077 0.6399 0.212 Uiso 0.604(12) 1 calc R U P B 2
H11D H 0.1296 0.0383 0.4464 0.212 Uiso 0.604(12) 1 calc R U P B 2
C12' C 0.2956(17) -0.0131(5) 0.406(2) 0.128(5) Uani 0.604(12) 1 d . . P B 2
H12C H 0.3246 0.0067 0.2907 0.154 Uiso 0.604(12) 1 calc R U P B 2
H12D H 0.3792 -0.0249 0.4839 0.154 Uiso 0.604(12) 1 calc R U P B 2
C13' C 0.2188(14) -0.0618(5) 0.3455(17) 0.190(6) Uani 0.604(12) 1 d . . P B 2
H13D H 0.1994 -0.0841 0.4585 0.285 Uiso 0.604(12) 1 calc R U P B 2
H13E H 0.2719 -0.0844 0.2602 0.285 Uiso 0.604(12) 1 calc R U P B 2
H13F H 0.1324 -0.0504 0.2766 0.285 Uiso 0.604(12) 1 calc R U P B 2
F1 F 0.88186(14) 0.29701(6) 0.1509(2) 0.0485(4) Uani 1 1 d . . . . .
F2 F 0.61591(14) 0.29443(6) 0.2191(2) 0.0473(4) Uani 1 1 d . . . . .
F3 F 0.88775(15) 0.09440(7) 0.1216(3) 0.0680(5) Uani 1 1 d . . . . .
F4 F 0.61809(15) 0.09255(7) 0.1715(3) 0.0677(5) Uani 1 1 d . . . . .
N1 N 0.2793(2) 0.17986(10) 0.7070(3) 0.0492(6) Uani 1 1 d . . . . .
H1A H 0.3440 0.1750 0.8060 0.074 Uiso 1 1 calc R U . . .
H1B H 0.2188 0.2066 0.7389 0.074 Uiso 1 1 calc R U . . .
H1C H 0.3202 0.1908 0.6003 0.074 Uiso 1 1 calc R U . . .
O2 O 0.41383(16) 0.21859(9) 0.3730(2) 0.0496(5) Uani 1 1 d . . . . .
O1 O 0.37620(15) 0.16135(8) 0.1130(2) 0.0449(4) Uani 1 1 d . . . . .
O3 O 1.12221(18) 0.15778(9) 0.1831(3) 0.0501(5) Uani 1 1 d . . . . .
O4 O 1.09262(16) 0.23446(9) -0.0091(2) 0.0514(5) Uani 1 1 d . . . . .
H3 H 1.217(4) 0.1585(15) 0.156(5) 0.086(11) 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
C1 O4 1.212(3) . ?
C1 O3 1.292(3) . ?
C1 C2 1.509(3) . ?
C2 C8 1.380(3) . ?
C2 C3 1.383(3) . ?
C3 F1 1.346(3) . ?
C3 C4 1.379(3) . ?
C4 F2 1.345(3) . ?
C4 C5 1.380(3) . ?
C5 C7 1.382(3) . ?
C5 C6 1.525(3) . ?
C6 O2 1.230(3) . ?
C6 O1 1.263(3) . ?
C7 F4 1.341(3) . ?
C7 C8 1.384(3) . ?
C8 F3 1.343(3) . ?
C9 N1 1.470(4) . ?
C9 C10 1.476(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11' 1.516(8) . ?
C10 C11 1.516(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.12(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.42(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11' C12' 1.496(16) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' C13' 1.401(19) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O3 H3 0.94(3) . ?

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
O4 C1 O3 125.5(2) . . ?
O4 C1 C2 121.0(2) . . ?
O3 C1 C2 113.6(2) . . ?
C8 C2 C3 116.68(19) . . ?
C8 C2 C1 122.2(2) . . ?
C3 C2 C1 121.1(2) . . ?
F1 C3 C4 117.5(2) . . ?
F1 C3 C2 120.75(19) . . ?
C4 C3 C2 121.8(2) . . ?
F2 C4 C3 117.8(2) . . ?
F2 C4 C5 120.64(19) . . ?
C3 C4 C5 121.6(2) . . ?
C4 C5 C7 116.75(19) . . ?
C4 C5 C6 122.0(2) . . ?
C7 C5 C6 121.2(2) . . ?
O2 C6 O1 126.9(2) . . ?
O2 C6 C5 117.5(2) . . ?
O1 C6 C5 115.60(19) . . ?
F4 C7 C5 120.4(2) . . ?
F4 C7 C8 118.0(2) . . ?
C5 C7 C8 121.6(2) . . ?
F3 C8 C2 121.0(2) . . ?
F3 C8 C7 117.4(2) . . ?
C2 C8 C7 121.5(2) . . ?
N1 C9 C10 112.8(3) . . ?
N1 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11' 113.2(5) . . ?
C9 C10 C11 113.2(5) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 126.3(18) . . ?
C12 C11 H11A 105.8 . . ?
C10 C11 H11A 105.8 . . ?
C12 C11 H11B 105.8 . . ?
C10 C11 H11B 105.8 . . ?
H11A C11 H11B 106.2 . . ?
C11 C12 C13 145(3) . . ?
C11 C12 H12A 100.7 . . ?
C13 C12 H12A 100.7 . . ?
C11 C12 H12B 100.7 . . ?
C13 C12 H12B 100.7 . . ?
H12A C12 H12B 104.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12' C11' C10 113.9(9) . . ?
C12' C11' H11C 108.8 . . ?
C10 C11' H11C 108.8 . . ?
C12' C11' H11D 108.8 . . ?
C10 C11' H11D 108.8 . . ?
H11C C11' H11D 107.7 . . ?
C13' C12' C11' 112.9(13) . . ?
C13' C12' H12C 109.0 . . ?
C11' C12' H12C 109.0 . . ?
C13' C12' H12D 109.0 . . ?
C11' C12' H12D 109.0 . . ?
H12C C12' H12D 107.8 . . ?
C12' C13' H13D 109.5 . . ?
C12' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 O3 H3 114(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
O4 C1 C2 C8 140.0(3) . . . . ?
O3 C1 C2 C8 -39.5(3) . . . . ?
O4 C1 C2 C3 -37.6(3) . . . . ?
O3 C1 C2 C3 142.8(2) . . . . ?
C8 C2 C3 F1 -179.86(19) . . . . ?
C1 C2 C3 F1 -2.1(3) . . . . ?
C8 C2 C3 C4 1.9(3) . . . . ?
C1 C2 C3 C4 179.70(19) . . . . ?
F1 C3 C4 F2 -0.6(3) . . . . ?
C2 C3 C4 F2 177.66(18) . . . . ?
F1 C3 C4 C5 178.00(18) . . . . ?
C2 C3 C4 C5 -3.7(3) . . . . ?
F2 C4 C5 C7 -179.23(18) . . . . ?
C3 C4 C5 C7 2.2(3) . . . . ?
F2 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C6 -179.36(18) . . . . ?
C4 C5 C6 O2 -49.0(3) . . . . ?
C7 C5 C6 O2 129.4(3) . . . . ?
C4 C5 C6 O1 131.8(2) . . . . ?
C7 C5 C6 O1 -49.9(3) . . . . ?
C4 C5 C7 F4 179.6(2) . . . . ?
C6 C5 C7 F4 1.2(3) . . . . ?
C4 C5 C7 C8 0.9(3) . . . . ?
C6 C5 C7 C8 -177.5(2) . . . . ?
C3 C2 C8 F3 179.4(2) . . . . ?
C1 C2 C8 F3 1.6(4) . . . . ?
C3 C2 C8 C7 1.2(3) . . . . ?
C1 C2 C8 C7 -176.5(2) . . . . ?
F4 C7 C8 F3 0.4(4) . . . . ?
C5 C7 C8 F3 179.1(2) . . . . ?
F4 C7 C8 C2 178.6(2) . . . . ?
C5 C7 C8 C2 -2.7(4) . . . . ?
N1 C9 C10 C11' -173.6(4) . . . . ?
N1 C9 C10 C11 -173.6(4) . . . . ?
C9 C10 C11 C12 133(2) . . . . ?
C10 C11 C12 C13 -2(7) . . . . ?
C9 C10 C11' C12' 168.4(7) . . . . ?
C10 C11' C12' C13' -178.6(9) . . . . ?

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
N1 H1C O2 0.89 1.96 2.849(2) 177.0 .
N1 H1B O4 0.89 2.43 2.999(3) 121.7 4_466
N1 H1B O4 0.89 2.27 3.017(3) 141.3 1_456
N1 H1A O1 0.89 2.12 2.890(3) 144.3 1_556
O3 H3 O1 0.94(3) 1.57(3) 2.518(2) 179(3) 1_655

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_10-D
_database_code_depnum_ccdc_archive 'CCDC 1911929'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C4 H9 D3 N O'
_chemical_formula_sum            'C12 H9 D4 F4 N O5'
_chemical_formula_weight         331.24

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                   9.6156(18)
_cell_length_b                   17.699(3)
_cell_length_c                   9.019(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.26(2)
_cell_angle_gamma                90
_cell_volume                     1440.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7219
_cell_measurement_theta_min      2.258
_cell_measurement_theta_max      29.598

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7219
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_max         29.598
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4055
_reflns_number_gt                1915
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0387P)²+0.3518P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3409
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.0753(2) 0.69596(15) 0.1140(3) 0.0454(6) Uani 1 1 d . . . . .
C2 C 0.2152(2) 0.70781(13) 0.0740(3) 0.0389(5) Uani 1 1 d . . . . .
C3 C 0.2900(2) 0.64760(14) 0.0377(3) 0.0462(6) Uani 1 1 d . . . . .
C4 C 0.4169(2) 0.65836(14) 0.0020(3) 0.0432(6) Uani 1 1 d . . . . .
C5 C 0.4752(2) 0.72950(13) 0.0015(2) 0.0384(5) Uani 1 1 d . . . . .
C6 C 0.4007(2) 0.78920(13) 0.0375(3) 0.0435(6) Uani 1 1 d . . . . .
C7 C 0.2743(2) 0.77861(13) 0.0730(3) 0.0418(6) Uani 1 1 d . . . . .
C8 C 0.6176(2) 0.74235(14) -0.0310(3) 0.0429(6) Uani 1 1 d . . . . .
C9 C 0.8587(5) 0.5772(2) 0.7837(4) 0.1229(15) Uani 1 1 d . . . . .
H9A H 0.7673 0.5807 0.8041 0.184 Uiso 1 1 calc R U . . .
H9B H 0.9192 0.6204 0.8278 0.184 Uiso 1 1 calc R U . . .
H9C H 0.9103 0.5320 0.8313 0.184 Uiso 1 1 calc R U . . .
C10 C 0.7400(3) 0.51396(17) 0.5451(3) 0.0712(8) Uani 1 1 d . . . . .
H10A H 0.6585 0.5076 0.5840 0.085 Uiso 1 1 calc R U . . .
H10B H 0.7982 0.4679 0.5664 0.085 Uiso 1 1 calc R U . . .
C11 C 0.6810(3) 0.52856(16) 0.3718(3) 0.0633(7) Uani 1 1 d . . . . .
H11A H 0.6100 0.5696 0.3511 0.076 Uiso 1 1 calc R U . . .
H11B H 0.6283 0.4839 0.3189 0.076 Uiso 1 1 calc R U . . .
C12 C 0.7965(3) 0.54832(15) 0.3011(3) 0.0605(7) Uani 1 1 d . . . . .
H12A H 0.8742 0.5104 0.3316 0.073 Uiso 1 1 calc R U . . .
H12B H 0.7519 0.5477 0.1868 0.073 Uiso 1 1 calc R U . . .
F1 F 0.21008(14) 0.83957(8) 0.11159(19) 0.0642(4) Uani 1 1 d . . . . .
F2 F 0.45540(16) 0.85964(8) 0.0442(2) 0.0731(5) Uani 1 1 d . . . . .
F3 F 0.23843(15) 0.57692(8) 0.0337(2) 0.0759(5) Uani 1 1 d . . . . .
F4 F 0.48251(15) 0.59750(8) -0.0343(2) 0.0700(5) Uani 1 1 d . . . . .
D3 D 0.834(3) 0.7211(18) 0.047(3) 0.105(10) Uiso 1 1 d . . . . .
N1 N 0.8632(2) 0.62400(11) 0.3530(2) 0.0501(5) Uani 1 1 d . . . . .
D1A D 0.7930 0.6592 0.3211 0.075 Uiso 1 1 calc R U . . .
D1B D 0.9327 0.6331 0.3109 0.075 Uiso 1 1 calc R U . . .
D1C D 0.9036 0.6250 0.4579 0.075 Uiso 1 1 calc R U . . .
O1 O 0.07759(18) 0.65007(11) 0.2148(2) 0.0675(6) Uani 1 1 d . . . . .
O2 O -0.03257(17) 0.73642(11) 0.0330(2) 0.0624(5) Uani 1 1 d . . . . .
O3 O 0.72843(18) 0.70605(12) 0.0635(2) 0.0687(6) Uani 1 1 d . . . . .
O4 O 0.61983(17) 0.78324(11) -0.1363(2) 0.0596(5) Uani 1 1 d . . . . .
O5 O 0.8290(2) 0.57498(13) 0.6227(2) 0.0895(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
C1 O1 1.214(3) . ?
C1 O2 1.264(3) . ?
C1 C2 1.523(3) . ?
C2 C7 1.377(3) . ?
C2 C3 1.387(3) . ?
C3 F3 1.342(3) . ?
C3 C4 1.379(3) . ?
C4 F4 1.345(2) . ?
C4 C5 1.379(3) . ?
C5 C6 1.377(3) . ?
C5 C8 1.513(3) . ?
C6 F2 1.346(3) . ?
C6 C7 1.373(3) . ?
C7 F1 1.347(2) . ?
C8 O4 1.200(3) . ?
C8 O3 1.283(3) . ?
C9 O5 1.380(4) . ?
C10 O5 1.405(3) . ?
C10 C11 1.489(4) . ?
C11 C12 1.501(3) . ?
C12 N1 1.489(3) . ?

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 O2 127.61(19) . . ?
O1 C1 C2 118.8(2) . . ?
O2 C1 C2 113.6(2) . . ?
C7 C2 C3 116.65(17) . . ?
C7 C2 C1 121.8(2) . . ?
C3 C2 C1 121.5(2) . . ?
F3 C3 C4 118.1(2) . . ?
F3 C3 C2 120.39(18) . . ?
C4 C3 C2 121.5(2) . . ?
F4 C4 C3 118.3(2) . . ?
F4 C4 C5 120.32(17) . . ?
C3 C4 C5 121.4(2) . . ?
C6 C5 C4 117.03(17) . . ?
C6 C5 C8 120.7(2) . . ?
C4 C5 C8 122.3(2) . . ?
F2 C6 C7 118.6(2) . . ?
F2 C6 C5 119.62(17) . . ?
C7 C6 C5 121.7(2) . . ?
F1 C7 C6 118.2(2) . . ?
F1 C7 C2 119.97(17) . . ?
C6 C7 C2 121.8(2) . . ?
O4 C8 O3 126.12(19) . . ?
O4 C8 C5 120.6(2) . . ?
O3 C8 C5 113.3(2) . . ?
O5 C10 C11 109.6(2) . . ?
C10 C11 C12 114.7(2) . . ?
N1 C12 C11 112.2(2) . . ?
C9 O5 C10 114.5(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
O1 C1 C2 C7 -128.1(3) . . . . ?
O2 C1 C2 C7 52.6(3) . . . . ?
O1 C1 C2 C3 51.5(3) . . . . ?
O2 C1 C2 C3 -127.7(3) . . . . ?
C7 C2 C3 F3 -179.0(2) . . . . ?
C1 C2 C3 F3 1.4(3) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
F3 C3 C4 F4 -0.3(3) . . . . ?
C2 C3 C4 F4 -179.1(2) . . . . ?
F3 C3 C4 C5 179.1(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
F4 C4 C5 C6 179.0(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
F4 C4 C5 C8 -3.1(3) . . . . ?
C3 C4 C5 C8 177.5(2) . . . . ?
C4 C5 C6 F2 177.7(2) . . . . ?
C8 C5 C6 F2 -0.2(3) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C8 C5 C6 C7 -177.6(2) . . . . ?
F2 C6 C7 F1 0.7(3) . . . . ?
C5 C6 C7 F1 178.0(2) . . . . ?
F2 C6 C7 C2 -177.6(2) . . . . ?
C5 C6 C7 C2 -0.2(4) . . . . ?
C3 C2 C7 F1 -178.1(2) . . . . ?
C1 C2 C7 F1 1.6(3) . . . . ?
C3 C2 C7 C6 0.2(3) . . . . ?
C1 C2 C7 C6 179.8(2) . . . . ?
C6 C5 C8 O4 -58.8(3) . . . . ?
C4 C5 C8 O4 123.4(3) . . . . ?
C6 C5 C8 O3 121.0(3) . . . . ?
C4 C5 C8 O3 -56.8(3) . . . . ?
O5 C10 C11 C12 52.6(3) . . . . ?
C10 C11 C12 N1 -69.3(3) . . . . ?
C11 C10 O5 C9 164.3(3) . . . . ?

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
C11 H11A O4 0.97 2.61 3.379(3) 136.7 4_576
O3 D3 O1 1.11(3) 2.62(3) 3.308(2) 119(2) 1_655
O3 D3 O2 1.11(3) 1.36(3) 2.467(2) 177(3) 1_655
N1 D1A O3 0.89 2.34 2.874(3) 118.7 .
N1 D1A O4 0.89 2.10 2.888(2) 147.3 4_576
N1 D1B O1 0.89 1.90 2.792(2) 177.9 1_655
N1 D1C O5 0.89 2.06 2.708(3) 128.7 .

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_12-D
_database_code_depnum_ccdc_archive 'CCDC 1911933'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C3 H3 D2 N2'
_chemical_formula_sum            'C11 H3 D3 F4 N2 O4'
_chemical_formula_weight         309.18

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                   7.1303(6)
_cell_length_b                   17.4758(13)
_cell_length_c                   9.7449(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.380(8)
_cell_angle_gamma                90
_cell_volume                     1186.05(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6111
_cell_measurement_theta_min      2.331
_cell_measurement_theta_max      29.507

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_F_000             616.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6111
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.331
_diffrn_reflns_theta_max         29.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3309
_reflns_number_gt                2011
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2813
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.2395(3) 0.47687(13) 0.82758(19) 0.0321(4) Uani 1 1 d . . . . .
C2 C 0.2407(2) 0.46001(11) 0.67369(18) 0.0280(4) Uani 1 1 d . . . . .
C3 C 0.2409(2) 0.38638(11) 0.62207(18) 0.0275(4) Uani 1 1 d . . . . .
C4 C 0.2555(2) 0.37133(11) 0.48570(19) 0.0278(4) Uani 1 1 d . . . . .
C5 C 0.2631(2) 0.42975(11) 0.39038(18) 0.0269(4) Uani 1 1 d . . . . .
C6 C 0.2721(3) 0.41084(12) 0.24102(19) 0.0312(4) Uani 1 1 d . . . . .
C7 C 0.2580(3) 0.50352(11) 0.44084(19) 0.0312(4) Uani 1 1 d . . . . .
C8 C 0.2488(3) 0.51850(11) 0.57889(19) 0.0307(4) Uani 1 1 d . . . . .
C9 C 0.3541(3) 0.72264(14) 0.1961(3) 0.0495(6) Uani 1 1 d . . . . .
H9 H 0.4551 0.7499 0.2506 0.059 Uiso 1 1 calc R U . . .
C10 C 0.1629(3) 0.73839(14) 0.1829(2) 0.0481(6) Uani 1 1 d . . . . .
H10 H 0.1093 0.7778 0.2260 0.058 Uiso 1 1 calc R U . . .
C11 C 0.0671(3) 0.68420(12) 0.0931(2) 0.0423(5) Uani 1 1 d . . . . .
H11 H -0.0655 0.6803 0.0634 0.051 Uiso 1 1 calc R U . . .
F1 F 0.26672(17) 0.29778(7) 0.44948(12) 0.0434(3) Uani 1 1 d . . . . .
F2 F 0.22897(16) 0.32607(7) 0.70495(11) 0.0426(3) Uani 1 1 d . . . . .
F3 F 0.2531(2) 0.59167(7) 0.61886(13) 0.0518(4) Uani 1 1 d . . . . .
F4 F 0.2631(2) 0.56465(7) 0.35878(13) 0.0524(4) Uani 1 1 d . . . . .
D1 D 0.473(4) 0.6305(17) 0.109(3) 0.068(8) Uiso 1 1 d . . . . .
D4 D 0.336(4) 0.4546(17) 0.089(3) 0.071(8) Uiso 1 1 d . . . . .
N1 N 0.3707(3) 0.66196(12) 0.11810(19) 0.0430(5) Uani 1 1 d . . . . .
N2 N 0.1950(2) 0.63825(11) 0.05551(18) 0.0403(4) Uani 1 1 d . . . . .
D2 D 0.1693 0.5996 0.0001 0.048 Uiso 1 1 calc R U . . .
O1 O 0.34100(19) 0.43327(9) 0.91675(13) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.1406(2) 0.53072(10) 0.85128(15) 0.0517(5) Uani 1 1 d . . . . .
O3 O 0.2205(3) 0.34991(10) 0.18946(15) 0.0602(5) Uani 1 1 d . . . . .
O4 O 0.3425(2) 0.46615(10) 0.17814(15) 0.0447(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 O2 1.227(2) . ?
C1 O1 1.261(2) . ?
C1 C2 1.530(2) . ?
C2 C3 1.382(3) . ?
C2 C8 1.387(3) . ?
C3 F2 1.342(2) . ?
C3 C4 1.380(2) . ?
C4 F1 1.340(2) . ?
C4 C5 1.389(3) . ?
C5 C7 1.383(3) . ?
C5 C6 1.507(2) . ?
C6 O3 1.201(2) . ?
C6 O4 1.301(2) . ?
C7 F4 1.340(2) . ?
C7 C8 1.386(2) . ?
C8 F3 1.335(2) . ?
C9 N1 1.325(3) . ?
C9 C10 1.369(3) . ?
C10 C11 1.369(3) . ?
C11 N2 1.324(3) . ?
N1 N2 1.336(2) . ?

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
O2 C1 O1 127.00(17) . . ?
O2 C1 C2 117.14(18) . . ?
O1 C1 C2 115.86(17) . . ?
C3 C2 C8 116.12(15) . . ?
C3 C2 C1 122.46(18) . . ?
C8 C2 C1 121.38(17) . . ?
F2 C3 C4 117.22(17) . . ?
F2 C3 C2 120.48(15) . . ?
C4 C3 C2 122.29(17) . . ?
F1 C4 C3 117.22(17) . . ?
F1 C4 C5 121.06(15) . . ?
C3 C4 C5 121.70(17) . . ?
C7 C5 C4 116.09(15) . . ?
C7 C5 C6 123.88(17) . . ?
C4 C5 C6 120.03(17) . . ?
O3 C6 O4 125.16(17) . . ?
O3 C6 C5 121.72(18) . . ?
O4 C6 C5 113.11(17) . . ?
F4 C7 C5 121.68(15) . . ?
F4 C7 C8 116.22(17) . . ?
C5 C7 C8 122.11(17) . . ?
F3 C8 C7 117.46(17) . . ?
F3 C8 C2 120.87(15) . . ?
C7 C8 C2 121.65(17) . . ?
N1 C9 C10 108.5(2) . . ?
C11 C10 C9 105.8(2) . . ?
N2 C11 C10 108.51(19) . . ?
C9 N1 N2 108.62(17) . . ?
C11 N2 N1 108.65(18) . . ?

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
O2 C1 C2 C3 -141.0(2) . . . . ?
O1 C1 C2 C3 38.9(2) . . . . ?
O2 C1 C2 C8 41.4(3) . . . . ?
O1 C1 C2 C8 -138.74(19) . . . . ?
C8 C2 C3 F2 -178.43(15) . . . . ?
C1 C2 C3 F2 3.8(2) . . . . ?
C8 C2 C3 C4 2.3(3) . . . . ?
C1 C2 C3 C4 -175.38(16) . . . . ?
F2 C3 C4 F1 -3.4(2) . . . . ?
C2 C3 C4 F1 175.83(15) . . . . ?
F2 C3 C4 C5 178.09(15) . . . . ?
C2 C3 C4 C5 -2.7(3) . . . . ?
F1 C4 C5 C7 -177.49(16) . . . . ?
C3 C4 C5 C7 0.9(3) . . . . ?
F1 C4 C5 C6 3.7(3) . . . . ?
C3 C4 C5 C6 -177.88(16) . . . . ?
C7 C5 C6 O3 -157.7(2) . . . . ?
C4 C5 C6 O3 21.1(3) . . . . ?
C7 C5 C6 O4 23.2(3) . . . . ?
C4 C5 C6 O4 -158.03(17) . . . . ?
C4 C5 C7 F4 -179.55(16) . . . . ?
C6 C5 C7 F4 -0.8(3) . . . . ?
C4 C5 C7 C8 0.9(3) . . . . ?
C6 C5 C7 C8 179.67(17) . . . . ?
F4 C7 C8 F3 -2.5(3) . . . . ?
C5 C7 C8 F3 177.09(16) . . . . ?
F4 C7 C8 C2 179.29(16) . . . . ?
C5 C7 C8 C2 -1.1(3) . . . . ?
C3 C2 C8 F3 -178.65(16) . . . . ?
C1 C2 C8 F3 -0.9(3) . . . . ?
C3 C2 C8 C7 -0.5(3) . . . . ?
C1 C2 C8 C7 177.26(16) . . . . ?
N1 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 N2 0.4(3) . . . . ?
C10 C9 N1 N2 -0.2(3) . . . . ?
C10 C11 N2 N1 -0.5(2) . . . . ?
C9 N1 N2 C11 0.4(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
C9 H9 F2 0.93 2.57 3.044(3) 112.0 3_666
C11 H11 F1 0.93 2.49 3.059(2) 119.4 2
C11 H11 O3 0.93 2.53 3.118(3) 121.4 3_565
N1 D1 O1 0.93(3) 1.79(3) 2.722(2) 176(3) 3_666
N2 D2 O2 0.86 1.86 2.704(2) 166.0 1_554
O4 D4 O1 0.88(3) 1.73(3) 2.6091(18) 176(3) 1_554

_refine_diff_density_max         0.559
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.314

####################################################################### 
# 
# 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_4-D
_database_code_depnum_ccdc_archive 'CCDC 1911917'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C6 D H7 N'
_chemical_formula_sum            'C14 H7 D2 F4 N O4'
_chemical_formula_weight         333.23

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                   9.7549(6)
_cell_length_b                   14.2234(8)
_cell_length_c                   9.7356(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.178(5)
_cell_angle_gamma                90
_cell_volume                     1333.50(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10081
_cell_measurement_theta_min      2.115
_cell_measurement_theta_max      29.403

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             672.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10081
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.115
_diffrn_reflns_theta_max         29.403
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3692
_reflns_number_gt                2414
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0487P)²+0.4242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3207
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.58151(17) 0.09220(12) 0.15725(16) 0.0297(4) Uani 1 1 d . . . . .
C2 C 0.54695(17) 0.10872(11) 0.30161(15) 0.0273(3) Uani 1 1 d . . . . .
C3 C 0.41631(17) 0.09339(11) 0.33487(16) 0.0281(3) Uani 1 1 d . . . . .
C4 C 0.38860(16) 0.10549(11) 0.46798(16) 0.0281(3) Uani 1 1 d . . . . .
C5 C 0.48905(16) 0.13527(11) 0.57628(15) 0.0272(3) Uani 1 1 d . . . . .
C6 C 0.45728(18) 0.14695(12) 0.72381(16) 0.0300(4) Uani 1 1 d . . . . .
C7 C 0.61888(17) 0.15285(12) 0.54175(16) 0.0297(4) Uani 1 1 d . . . . .
C8 C 0.64751(17) 0.13924(12) 0.40898(16) 0.0305(4) Uani 1 1 d . . . . .
C9 C 0.02293(19) 0.09595(13) 0.83336(19) 0.0388(4) Uani 1 1 d . . . . .
C10 C -0.0855(2) 0.10298(14) 0.9074(2) 0.0459(5) Uani 1 1 d . . . . .
H10 H -0.1710 0.0761 0.8728 0.055 Uiso 1 1 calc R U . . .
C11 C -0.0675(2) 0.14961(15) 1.0324(2) 0.0529(5) Uani 1 1 d . . . . .
H11 H -0.1410 0.1544 1.0822 0.063 Uiso 1 1 calc R U . . .
C12 C 0.0592(2) 0.18937(15) 1.0845(2) 0.0521(5) Uani 1 1 d . . . . .
H12 H 0.0724 0.2204 1.1696 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1639(2) 0.18217(14) 1.0088(2) 0.0453(5) Uani 1 1 d . . . . .
H13 H 0.2498 0.2091 1.0414 0.054 Uiso 1 1 calc R U . . .
C14 C 0.0154(3) 0.04715(18) 0.6970(2) 0.0612(6) Uani 1 1 d . . . . .
H14A H 0.0056 0.0929 0.6235 0.092 Uiso 1 1 calc R U . . .
H14B H -0.0631 0.0056 0.6836 0.092 Uiso 1 1 calc R U . . .
H14C H 0.0989 0.0116 0.6960 0.092 Uiso 1 1 calc R U . . .
F1 F 0.77637(11) 0.15851(9) 0.38434(10) 0.0476(3) Uani 1 1 d . . . . .
F2 F 0.72138(11) 0.18674(9) 0.63767(10) 0.0468(3) Uani 1 1 d . . . . .
F3 F 0.25938(10) 0.08441(8) 0.49062(10) 0.0450(3) Uani 1 1 d . . . . .
F4 F 0.31239(10) 0.06364(8) 0.23732(10) 0.0417(3) Uani 1 1 d . . . . .
D1 D 0.214(3) 0.1336(16) 0.833(2) 0.063(7) Uiso 1 1 d . . . . .
D3 D 0.524(3) 0.1286(19) -0.026(3) 0.100(10) Uiso 1 1 d . . . . .
N1 N 0.14389(16) 0.13658(12) 0.88786(17) 0.0404(4) Uani 1 1 d . . . . .
O1 O 0.34327(13) 0.18109(9) 0.73661(12) 0.0405(3) Uani 1 1 d . . . . .
O2 O 0.55099(14) 0.11942(10) 0.81820(11) 0.0444(3) Uani 1 1 d . . . . .
O3 O 0.49620(14) 0.13459(10) 0.06147(12) 0.0420(3) Uani 1 1 d . . . . .
O4 O 0.68003(14) 0.04509(10) 0.14036(13) 0.0453(3) 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 O4 1.204(2) . ?
C1 O3 1.295(2) . ?
C1 C2 1.515(2) . ?
C2 C3 1.381(2) . ?
C2 C8 1.384(2) . ?
C3 F4 1.3421(18) . ?
C3 C4 1.376(2) . ?
C4 F3 1.3477(18) . ?
C4 C5 1.386(2) . ?
C5 C7 1.384(2) . ?
C5 C6 1.526(2) . ?
C6 O1 1.238(2) . ?
C6 O2 1.251(2) . ?
C7 F2 1.3439(18) . ?
C7 C8 1.379(2) . ?
C8 F1 1.3449(18) . ?
C9 N1 1.345(2) . ?
C9 C10 1.375(3) . ?
C9 C14 1.489(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.355(3) . ?
C13 N1 1.331(3) . ?

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
O4 C1 O3 126.57(15) . . ?
O4 C1 C2 120.90(15) . . ?
O3 C1 C2 112.52(14) . . ?
C3 C2 C8 116.21(14) . . ?
C3 C2 C1 122.89(14) . . ?
C8 C2 C1 120.89(14) . . ?
F4 C3 C4 117.78(14) . . ?
F4 C3 C2 120.32(13) . . ?
C4 C3 C2 121.88(15) . . ?
F3 C4 C3 117.10(14) . . ?
F3 C4 C5 120.64(13) . . ?
C3 C4 C5 122.23(14) . . ?
C7 C5 C4 115.70(14) . . ?
C7 C5 C6 122.69(14) . . ?
C4 C5 C6 121.61(14) . . ?
O1 C6 O2 127.71(15) . . ?
O1 C6 C5 117.26(14) . . ?
O2 C6 C5 115.02(14) . . ?
F2 C7 C8 117.53(14) . . ?
F2 C7 C5 120.28(13) . . ?
C8 C7 C5 122.16(15) . . ?
F1 C8 C7 118.25(14) . . ?
F1 C8 C2 119.94(14) . . ?
C7 C8 C2 121.79(15) . . ?
N1 C9 C10 117.50(18) . . ?
N1 C9 C14 117.86(17) . . ?
C10 C9 C14 124.64(19) . . ?
C11 C10 C9 120.00(19) . . ?
C10 C11 C12 120.23(19) . . ?
C13 C12 C11 118.6(2) . . ?
N1 C13 C12 120.04(19) . . ?
C13 N1 C9 123.65(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
O4 C1 C2 C3 -128.80(19) . . . . ?
O3 C1 C2 C3 52.1(2) . . . . ?
O4 C1 C2 C8 50.2(2) . . . . ?
O3 C1 C2 C8 -128.87(17) . . . . ?
C8 C2 C3 F4 -179.94(15) . . . . ?
C1 C2 C3 F4 -0.9(2) . . . . ?
C8 C2 C3 C4 -1.6(2) . . . . ?
C1 C2 C3 C4 177.50(15) . . . . ?
F4 C3 C4 F3 1.4(2) . . . . ?
C2 C3 C4 F3 -176.97(15) . . . . ?
F4 C3 C4 C5 179.52(15) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
F3 C4 C5 C7 178.55(15) . . . . ?
C3 C4 C5 C7 0.5(2) . . . . ?
F3 C4 C5 C6 -1.0(2) . . . . ?
C3 C4 C5 C6 -179.08(15) . . . . ?
C7 C5 C6 O1 140.57(17) . . . . ?
C4 C5 C6 O1 -39.9(2) . . . . ?
C7 C5 C6 O2 -40.1(2) . . . . ?
C4 C5 C6 O2 139.44(17) . . . . ?
C4 C5 C7 F2 176.49(15) . . . . ?
C6 C5 C7 F2 -3.9(2) . . . . ?
C4 C5 C7 C8 -1.6(2) . . . . ?
C6 C5 C7 C8 177.94(15) . . . . ?
F2 C7 C8 F1 1.5(2) . . . . ?
C5 C7 C8 F1 179.69(15) . . . . ?
F2 C7 C8 C2 -176.99(15) . . . . ?
C5 C7 C8 C2 1.2(3) . . . . ?
C3 C2 C8 F1 -178.01(15) . . . . ?
C1 C2 C8 F1 2.9(2) . . . . ?
C3 C2 C8 C7 0.5(3) . . . . ?
C1 C2 C8 C7 -178.64(15) . . . . ?
N1 C9 C10 C11 -0.4(3) . . . . ?
C14 C9 C10 C11 180.0(2) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 N1 -0.8(3) . . . . ?
C12 C13 N1 C9 0.2(3) . . . . ?
C10 C9 N1 C13 0.4(3) . . . . ?
C14 C9 N1 C13 -179.95(19) . . . . ?

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
O3 D3 O2 0.94(3) 1.59(3) 2.5190(16) 172(3) 1_554
N1 D1 O1 0.93(2) 1.82(2) 2.695(2) 156(2) .
C14 H14C O4 0.96 2.60 3.399(3) 141.3 3_656
C13 H13 O3 0.93 2.61 3.271(2) 128.9 1_556
C13 H13 O1 0.93 2.52 3.244(2) 135.4 4_566
C10 H10 F4 0.93 2.56 3.392(2) 149.8 3_556

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_11-D
_database_code_depnum_ccdc_archive 'CCDC 1911931'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C3 H3 D2 N2'
_chemical_formula_sum            'C11 H3 D3 F4 N2 O4'
_chemical_formula_weight         309.18

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   9.7270(5)
_cell_length_b                   7.2158(5)
_cell_length_c                   17.3952(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1220.94(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9385
_cell_measurement_theta_min      2.342
_cell_measurement_theta_max      29.595

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             616.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9385
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.342
_diffrn_reflns_theta_max         29.595
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.786
_diffrn_reflns_point_group_measured_fraction_full 0.905
_reflns_number_total             3421
_reflns_number_gt                2277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_max     0.644
_reflns_Friedel_fraction_full    0.804

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0457P)²+0.0094P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 798 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2689
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.3218(3) 0.4412(3) 0.43475(17) 0.0281(6) Uani 1 1 d . . . . .
C2 C 0.1716(3) 0.4696(4) 0.45236(16) 0.0272(6) Uani 1 1 d . . . . .
C3 C 0.0844(3) 0.5426(4) 0.39749(17) 0.0281(6) Uani 1 1 d . . . . .
C4 C -0.0526(3) 0.5706(4) 0.41201(17) 0.0274(6) Uani 1 1 d . . . . .
C5 C -0.1113(2) 0.5272(3) 0.48234(17) 0.0249(5) Uani 1 1 d . . . . .
C6 C -0.2634(2) 0.5557(3) 0.49780(15) 0.0252(6) Uani 1 1 d . . . . .
C7 C -0.0234(3) 0.4550(3) 0.53773(15) 0.0276(6) Uani 1 1 d . . . . .
C8 C 0.1139(3) 0.4267(3) 0.52311(16) 0.0275(6) Uani 1 1 d . . . . .
C9 C 0.5459(3) 0.5046(4) 0.24505(19) 0.0485(8) Uani 1 1 d . . . . .
H9 H 0.4830 0.5906 0.2638 0.058 Uiso 1 1 calc R U . . .
C10 C 0.5575(4) 0.4482(5) 0.1727(2) 0.0504(9) Uani 1 1 d . . . . .
H10 H 0.5043 0.4865 0.1313 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7117(3) 0.3050(5) 0.24087(19) 0.0482(8) Uani 1 1 d . . . . .
H11 H 0.7838 0.2277 0.2553 0.058 Uiso 1 1 calc R U . . .
F1 F 0.13370(16) 0.5913(3) 0.32795(10) 0.0442(4) Uani 1 1 d . . . . .
F2 F -0.12956(15) 0.6475(3) 0.35640(10) 0.0432(4) Uani 1 1 d . . . . .
F3 F -0.07169(17) 0.4078(3) 0.60713(9) 0.0419(4) Uani 1 1 d . . . . .
F4 F 0.19178(16) 0.3510(2) 0.57832(10) 0.0435(4) Uani 1 1 d . . . . .
D1 D 0.657(5) 0.424(5) 0.337(3) 0.072(13) Uiso 1 1 d . . . . .
D2 D 0.695(4) 0.265(5) 0.128(2) 0.066(12) Uiso 1 1 d . . . . .
D3 D 0.480(5) 0.505(7) 0.477(2) 0.064(11) Uiso 1 1 d . . . . .
N1 N 0.6431(3) 0.4132(4) 0.28656(18) 0.0475(7) Uani 1 1 d . . . . .
N2 N 0.6627(3) 0.3229(4) 0.17102(16) 0.0423(6) Uani 1 1 d . . . . .
O1 O -0.29791(19) 0.6351(3) 0.55754(11) 0.0382(5) Uani 1 1 d . . . . .
O2 O -0.34451(18) 0.4914(3) 0.44777(11) 0.0358(5) Uani 1 1 d . . . . .
O3 O 0.4025(2) 0.5149(3) 0.48703(13) 0.0392(5) Uani 1 1 d . . . . .
O4 O 0.35982(19) 0.3606(3) 0.37838(12) 0.0427(5) 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 O4 1.199(3) . ?
C1 O3 1.314(3) . ?
C1 C2 1.507(4) . ?
C2 C3 1.381(4) . ?
C2 C8 1.388(4) . ?
C3 F1 1.348(3) . ?
C3 C4 1.371(4) . ?
C4 F2 1.343(3) . ?
C4 C5 1.386(4) . ?
C5 C7 1.390(4) . ?
C5 C6 1.518(3) . ?
C6 O1 1.233(3) . ?
C6 O2 1.263(3) . ?
C7 F3 1.339(3) . ?
C7 C8 1.375(4) . ?
C8 F4 1.340(3) . ?
C9 C10 1.327(5) . ?
C9 N1 1.360(4) . ?
C10 N2 1.365(4) . ?
C11 N1 1.299(4) . ?
C11 N2 1.312(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 C1 O3 125.3(2) . . ?
O4 C1 C2 122.1(3) . . ?
O3 C1 C2 112.6(2) . . ?
C3 C2 C8 116.7(2) . . ?
C3 C2 C1 120.5(3) . . ?
C8 C2 C1 122.8(2) . . ?
F1 C3 C4 118.2(2) . . ?
F1 C3 C2 120.1(2) . . ?
C4 C3 C2 121.7(3) . . ?
F2 C4 C3 118.0(3) . . ?
F2 C4 C5 120.0(2) . . ?
C3 C4 C5 122.0(2) . . ?
C4 C5 C7 116.3(2) . . ?
C4 C5 C6 121.8(2) . . ?
C7 C5 C6 121.9(3) . . ?
O1 C6 O2 125.6(2) . . ?
O1 C6 C5 118.5(2) . . ?
O2 C6 C5 115.9(2) . . ?
F3 C7 C8 118.0(2) . . ?
F3 C7 C5 120.3(2) . . ?
C8 C7 C5 121.7(2) . . ?
F4 C8 C7 118.5(2) . . ?
F4 C8 C2 119.9(2) . . ?
C7 C8 C2 121.6(2) . . ?
C10 C9 N1 107.2(3) . . ?
C9 C10 N2 106.7(3) . . ?
N1 C11 N2 108.7(3) . . ?
C11 N1 C9 108.9(3) . . ?
C11 N2 C10 108.5(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
O4 C1 C2 C3 -50.9(4) . . . . ?
O3 C1 C2 C3 128.6(3) . . . . ?
O4 C1 C2 C8 129.6(3) . . . . ?
O3 C1 C2 C8 -50.8(3) . . . . ?
C8 C2 C3 F1 178.6(2) . . . . ?
C1 C2 C3 F1 -0.9(4) . . . . ?
C8 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 -179.7(2) . . . . ?
F1 C3 C4 F2 -0.9(4) . . . . ?
C2 C3 C4 F2 178.0(2) . . . . ?
F1 C3 C4 C5 -179.0(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
F2 C4 C5 C7 -177.5(2) . . . . ?
C3 C4 C5 C7 0.6(4) . . . . ?
F2 C4 C5 C6 2.9(4) . . . . ?
C3 C4 C5 C6 -179.1(2) . . . . ?
C4 C5 C6 O1 -131.9(3) . . . . ?
C7 C5 C6 O1 48.5(3) . . . . ?
C4 C5 C6 O2 49.3(3) . . . . ?
C7 C5 C6 O2 -130.3(3) . . . . ?
C4 C5 C7 F3 -179.5(2) . . . . ?
C6 C5 C7 F3 0.1(4) . . . . ?
C4 C5 C7 C8 -0.6(4) . . . . ?
C6 C5 C7 C8 179.0(2) . . . . ?
F3 C7 C8 F4 1.0(4) . . . . ?
C5 C7 C8 F4 -177.8(2) . . . . ?
F3 C7 C8 C2 179.1(2) . . . . ?
C5 C7 C8 C2 0.3(4) . . . . ?
C3 C2 C8 F4 178.3(2) . . . . ?
C1 C2 C8 F4 -2.3(4) . . . . ?
C3 C2 C8 C7 0.2(4) . . . . ?
C1 C2 C8 C7 179.6(2) . . . . ?
N1 C9 C10 N2 -0.3(4) . . . . ?
N2 C11 N1 C9 0.0(4) . . . . ?
C10 C9 N1 C11 0.1(4) . . . . ?
N1 C11 N2 C10 -0.2(4) . . . . ?
C9 C10 N2 C11 0.3(4) . . . . ?

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
C10 H10 O1 0.93 2.54 3.279(4) 136.8 2_564
C11 H11 O4 0.93 2.35 3.037(4) 130.1 3
O3 D3 O2 0.78(4) 1.78(4) 2.560(2) 176(5) 1_655
N2 D2 O1 0.91(4) 1.84(4) 2.732(3) 166(3) 4_544
N1 D1 O2 0.90(5) 1.98(5) 2.863(4) 167(4) 1_655

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_8-D
_database_code_depnum_ccdc_archive 'CCDC 1911925'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 D F4 O4, C4 H9 D3 N'
_chemical_formula_sum            'C12 H9 D4 F4 N O4'
_chemical_formula_weight         315.24

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                   9.5827(15)
_cell_length_b                   20.741(3)
_cell_length_c                   6.8689(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.476(13)
_cell_angle_gamma                90
_cell_volume                     1361.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5785
_cell_measurement_theta_min      1.964
_cell_measurement_theta_max      25.004

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             640.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5785
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.964
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_full        25.004
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2401
_reflns_number_gt                1411
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0834P)²+0.6388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2402
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0747
_refine_ls_wR_factor_ref         0.2123
_refine_ls_wR_factor_gt          0.1737
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 1.0941(4) 0.1814(2) 0.8397(6) 0.0367(10) Uani 1 1 d . . . . .
C2 C 0.9389(4) 0.1829(2) 0.8740(5) 0.0349(10) Uani 1 1 d . . . . .
C3 C 0.8652(4) 0.1275(2) 0.9021(6) 0.0422(11) Uani 1 1 d . . . . .
C4 C 0.7218(4) 0.1286(2) 0.9269(6) 0.0423(11) Uani 1 1 d . . . . .
C5 C 0.6502(4) 0.1859(2) 0.9347(5) 0.0356(10) Uani 1 1 d . . . . .
C6 C 0.4970(4) 0.1887(2) 0.9719(6) 0.0403(11) Uani 1 1 d . . . . .
C7 C 0.7252(4) 0.2415(2) 0.9103(5) 0.0347(10) Uani 1 1 d . . . . .
C8 C 0.8659(4) 0.2399(2) 0.8762(5) 0.0342(10) Uani 1 1 d . . . . .
C9 C 0.3387(5) 0.1113(3) 0.4044(7) 0.0626(14) Uani 1 1 d . . . . .
H9A H 0.4120 0.1168 0.5087 0.075 Uiso 1 1 calc R U . . .
H9B H 0.3815 0.0964 0.2892 0.075 Uiso 1 1 calc R U . . .
C10 C 0.2335(7) 0.0617(3) 0.4642(10) 0.0908(19) Uani 1 1 d . . . . .
H10A H 0.1803 0.0806 0.5644 0.109 Uiso 1 1 calc R U . . .
H10B H 0.1684 0.0527 0.3522 0.109 Uiso 1 1 calc R U . . .
C11 C 0.2924(9) 0.0008(4) 0.5376(12) 0.116(2) Uani 1 1 d . . . . .
H11A H 0.3593 0.0095 0.6478 0.140 Uiso 1 1 calc R U . . .
H11B H 0.3426 -0.0192 0.4363 0.140 Uiso 1 1 calc R U . . .
C12 C 0.1857(9) -0.0451(3) 0.5998(11) 0.125(3) Uani 1 1 d . . . . .
H12A H 0.1161 -0.0521 0.4937 0.187 Uiso 1 1 calc R U . . .
H12B H 0.1422 -0.0275 0.7093 0.187 Uiso 1 1 calc R U . . .
H12C H 0.2299 -0.0853 0.6366 0.187 Uiso 1 1 calc R U . . .
F1 F 0.6636(2) 0.29964(12) 0.9163(3) 0.0505(7) Uani 1 1 d . . . . .
F2 F 0.9290(2) 0.29679(12) 0.8481(3) 0.0490(7) Uani 1 1 d . . . . .
F3 F 0.6583(3) 0.07180(13) 0.9504(4) 0.0647(8) Uani 1 1 d . . . . .
F4 F 0.9284(2) 0.06965(13) 0.9014(4) 0.0623(8) Uani 1 1 d . . . . .
D3 D 0.324(7) 0.150(3) 0.911(9) 0.12(2) Uiso 1 1 d . . . . .
N1 N 0.2682(4) 0.17295(18) 0.3630(5) 0.0528(11) Uani 1 1 d . . . . .
D1A D 0.2238 0.1850 0.4661 0.079 Uiso 1 1 calc R U . . .
D1B D 0.2067 0.1686 0.2599 0.079 Uiso 1 1 calc R U . . .
D1C D 0.3313 0.2027 0.3378 0.079 Uiso 1 1 calc R U . . .
O1 O 1.1314(3) 0.21152(16) 0.6983(4) 0.0526(9) Uani 1 1 d . . . . .
O2 O 1.1700(3) 0.14877(15) 0.9595(4) 0.0471(8) Uani 1 1 d . . . . .
O3 O 0.4235(3) 0.14317(16) 0.8874(4) 0.0518(9) Uani 1 1 d . . . . .
O4 O 0.4539(3) 0.23064(17) 1.0735(4) 0.0534(9) 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 1.232(5) . ?
C1 O2 1.253(5) . ?
C1 C2 1.524(5) . ?
C2 C3 1.369(6) . ?
C2 C8 1.375(6) . ?
C3 F4 1.345(5) . ?
C3 C4 1.398(6) . ?
C4 F3 1.341(5) . ?
C4 C5 1.377(6) . ?
C5 C7 1.375(6) . ?
C5 C6 1.511(6) . ?
C6 O4 1.208(5) . ?
C6 O3 1.289(5) . ?
C7 F1 1.344(4) . ?
C7 C8 1.387(5) . ?
C8 F2 1.346(5) . ?
C9 N1 1.464(6) . ?
C9 C10 1.518(8) . ?
C10 C11 1.458(8) . ?
C11 C12 1.483(10) . ?

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 O2 127.1(4) . . ?
O1 C1 C2 117.3(3) . . ?
O2 C1 C2 115.7(3) . . ?
C3 C2 C8 116.9(4) . . ?
C3 C2 C1 121.6(4) . . ?
C8 C2 C1 121.5(4) . . ?
F4 C3 C2 120.7(4) . . ?
F4 C3 C4 117.5(4) . . ?
C2 C3 C4 121.8(4) . . ?
F3 C4 C5 121.5(3) . . ?
F3 C4 C3 117.4(4) . . ?
C5 C4 C3 121.0(4) . . ?
C7 C5 C4 116.9(4) . . ?
C7 C5 C6 120.8(4) . . ?
C4 C5 C6 122.2(4) . . ?
O4 C6 O3 126.0(4) . . ?
O4 C6 C5 120.4(4) . . ?
O3 C6 C5 113.6(4) . . ?
F1 C7 C5 120.9(3) . . ?
F1 C7 C8 117.4(4) . . ?
C5 C7 C8 121.7(4) . . ?
F2 C8 C2 121.2(3) . . ?
F2 C8 C7 117.2(4) . . ?
C2 C8 C7 121.6(4) . . ?
N1 C9 C10 109.8(4) . . ?
C11 C10 C9 115.7(6) . . ?
C10 C11 C12 113.5(7) . . ?

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
O1 C1 C2 C3 129.5(4) . . . . ?
O2 C1 C2 C3 -50.1(5) . . . . ?
O1 C1 C2 C8 -49.8(5) . . . . ?
O2 C1 C2 C8 130.6(4) . . . . ?
C8 C2 C3 F4 179.8(3) . . . . ?
C1 C2 C3 F4 0.4(6) . . . . ?
C8 C2 C3 C4 1.6(6) . . . . ?
C1 C2 C3 C4 -177.7(3) . . . . ?
F4 C3 C4 F3 0.8(6) . . . . ?
C2 C3 C4 F3 179.0(4) . . . . ?
F4 C3 C4 C5 178.2(4) . . . . ?
C2 C3 C4 C5 -3.6(6) . . . . ?
F3 C4 C5 C7 179.5(3) . . . . ?
C3 C4 C5 C7 2.2(6) . . . . ?
F3 C4 C5 C6 0.6(6) . . . . ?
C3 C4 C5 C6 -176.7(4) . . . . ?
C7 C5 C6 O4 -37.6(5) . . . . ?
C4 C5 C6 O4 141.3(4) . . . . ?
C7 C5 C6 O3 142.7(4) . . . . ?
C4 C5 C6 O3 -38.4(5) . . . . ?
C4 C5 C7 F1 -179.8(3) . . . . ?
C6 C5 C7 F1 -0.9(5) . . . . ?
C4 C5 C7 C8 1.0(5) . . . . ?
C6 C5 C7 C8 179.9(3) . . . . ?
C3 C2 C8 F2 -179.4(3) . . . . ?
C1 C2 C8 F2 0.0(5) . . . . ?
C3 C2 C8 C7 1.6(5) . . . . ?
C1 C2 C8 C7 -179.1(3) . . . . ?
F1 C7 C8 F2 -1.3(5) . . . . ?
C5 C7 C8 F2 177.9(3) . . . . ?
F1 C7 C8 C2 177.8(3) . . . . ?
C5 C7 C8 C2 -3.0(5) . . . . ?
N1 C9 C10 C11 -171.3(6) . . . . ?
C9 C10 C11 C12 178.2(6) . . . . ?

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
N1 D1C O4 0.89 2.37 2.975(5) 125.4 4_565
N1 D1C O4 0.89 2.31 3.017(5) 136.1 1_554
N1 D1B O2 0.89 2.11 2.900(4) 148.0 1_454
N1 D1A O1 0.89 1.96 2.852(4) 178.3 1_455
O3 D3 O2 0.99(7) 1.54(7) 2.519(4) 170(6) 1_455
O3 D3 O1 0.99(7) 2.60(6) 3.311(4) 129(5) 1_455
C9 H9A O3 0.97 2.65 3.418(6) 136.1 .

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_12-H
_database_code_depnum_ccdc_archive 'CCDC 1911932'
loop_
_audit_author_name
_audit_author_address
'Tong Jin'
;southeast univerity
China
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-06-26 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         'C8 H F4 O4, C3 H5 N2'
_chemical_formula_sum            'C11 H6 F4 N2 O4'
_chemical_formula_weight         306.18

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                   7.1345(5)
_cell_length_b                   17.4678(13)
_cell_length_c                   9.7338(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.264(7)
_cell_angle_gamma                90
_cell_volume                     1185.38(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6065
_cell_measurement_theta_min      2.332
_cell_measurement_theta_max      29.462

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_F_000             616.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6065
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         29.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3284
_reflns_number_gt                1965
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0630P)²+0.1035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
C1 C 0.2603(3) 0.47674(14) 0.6725(2) 0.0333(5) Uani 1 1 d . . . . .
C2 C 0.2592(2) 0.46012(12) 0.82617(19) 0.0293(4) Uani 1 1 d . . . . .
C3 C 0.2584(2) 0.38640(12) 0.8777(2) 0.0298(4) Uani 1 1 d . . . . .
C4 C 0.2445(2) 0.37134(12) 1.0141(2) 0.0284(4) Uani 1 1 d . . . . .
C5 C 0.2373(2) 0.42970(12) 1.1098(2) 0.0289(4) Uani 1 1 d . . . . .
C6 C 0.2279(3) 0.41069(13) 1.2593(2) 0.0331(5) Uani 1 1 d . . . . .
C7 C 0.2418(3) 0.50358(12) 1.0595(2) 0.0323(5) Uani 1 1 d . . . . .
C8 C 0.2513(3) 0.51852(12) 0.9210(2) 0.0319(4) Uani 1 1 d . . . . .
C9 C 0.1465(3) 0.72247(15) 0.3046(3) 0.0511(6) Uani 1 1 d . . . . .
H9 H 0.0455 0.7498 0.2502 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3373(3) 0.73856(14) 0.3173(3) 0.0488(6) Uani 1 1 d . . . . .
H10 H 0.3908 0.7780 0.2740 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4325(3) 0.68448(14) 0.4070(2) 0.0440(6) Uani 1 1 d . . . . .
H11 H 0.5649 0.6807 0.4367 0.053 Uiso 1 1 calc R U . . .
F1 F 0.27077(17) 0.32607(8) 0.79464(12) 0.0442(4) Uani 1 1 d . . . . .
F2 F 0.23285(18) 0.29794(7) 1.05024(13) 0.0449(3) Uani 1 1 d . . . . .
F3 F 0.2469(2) 0.59166(8) 0.88097(14) 0.0532(4) Uani 1 1 d . . . . .
F4 F 0.2376(2) 0.56451(8) 1.14154(14) 0.0537(4) Uani 1 1 d . . . . .
H1 H 0.027(4) 0.6330(18) 0.394(3) 0.071(9) Uiso 1 1 d . . . . .
H2 H 0.318(3) 0.5984(16) 0.505(3) 0.051(7) Uiso 1 1 d . . . . .
H4 H 0.154(4) 0.4539(19) 1.409(3) 0.077(9) Uiso 1 1 d . . . . .
N1 N 0.1294(3) 0.66187(13) 0.3821(2) 0.0445(5) Uani 1 1 d . . . . .
N2 N 0.3052(2) 0.63832(13) 0.4448(2) 0.0408(5) Uani 1 1 d . . . . .
O1 O 0.15889(19) 0.43336(9) 0.58305(14) 0.0392(4) Uani 1 1 d . . . . .
O2 O 0.3587(2) 0.53082(11) 0.64844(16) 0.0533(5) Uani 1 1 d . . . . .
O3 O 0.2804(3) 0.34975(11) 1.31110(17) 0.0626(5) Uani 1 1 d . . . . .
O4 O 0.1574(2) 0.46584(10) 1.32246(17) 0.0462(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 O2 1.228(3) . ?
C1 O1 1.260(3) . ?
C1 C2 1.526(3) . ?
C2 C3 1.383(3) . ?
C2 C8 1.385(3) . ?
C3 F1 1.343(2) . ?
C3 C4 1.377(3) . ?
C4 F2 1.337(2) . ?
C4 C5 1.389(3) . ?
C5 C7 1.383(3) . ?
C5 C6 1.508(3) . ?
C6 O3 1.203(3) . ?
C6 O4 1.300(3) . ?
C7 F4 1.334(2) . ?
C7 C8 1.389(3) . ?
C8 F3 1.334(2) . ?
C9 N1 1.321(3) . ?
C9 C10 1.369(3) . ?
C10 C11 1.365(3) . ?
C11 N2 1.323(3) . ?
N1 N2 1.338(3) . ?

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
O2 C1 O1 126.74(18) . . ?
O2 C1 C2 117.09(19) . . ?
O1 C1 C2 116.17(18) . . ?
C3 C2 C8 116.12(17) . . ?
C3 C2 C1 122.32(19) . . ?
C8 C2 C1 121.52(19) . . ?
F1 C3 C4 117.26(18) . . ?
F1 C3 C2 120.43(17) . . ?
C4 C3 C2 122.31(19) . . ?
F2 C4 C3 117.25(18) . . ?
F2 C4 C5 120.96(17) . . ?
C3 C4 C5 121.76(19) . . ?
C7 C5 C4 116.18(17) . . ?
C7 C5 C6 123.76(19) . . ?
C4 C5 C6 120.06(18) . . ?
O3 C6 O4 125.1(2) . . ?
O3 C6 C5 121.7(2) . . ?
O4 C6 C5 113.20(19) . . ?
F4 C7 C5 121.85(17) . . ?
F4 C7 C8 116.28(19) . . ?
C5 C7 C8 121.87(19) . . ?
F3 C8 C2 120.83(17) . . ?
F3 C8 C7 117.41(19) . . ?
C2 C8 C7 121.73(19) . . ?
N1 C9 C10 108.9(2) . . ?
C11 C10 C9 105.4(2) . . ?
N2 C11 C10 108.8(2) . . ?
C9 N1 N2 108.41(19) . . ?
C11 N2 N1 108.5(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
O2 C1 C2 C3 -141.5(2) . . . . ?
O1 C1 C2 C3 38.8(3) . . . . ?
O2 C1 C2 C8 41.1(3) . . . . ?
O1 C1 C2 C8 -138.60(19) . . . . ?
C8 C2 C3 F1 -178.25(15) . . . . ?
C1 C2 C3 F1 4.2(3) . . . . ?
C8 C2 C3 C4 1.9(3) . . . . ?
C1 C2 C3 C4 -175.59(16) . . . . ?
F1 C3 C4 F2 -3.9(2) . . . . ?
C2 C3 C4 F2 175.88(15) . . . . ?
F1 C3 C4 C5 177.89(15) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
F2 C4 C5 C7 -177.16(16) . . . . ?
C3 C4 C5 C7 0.9(3) . . . . ?
F2 C4 C5 C6 3.7(3) . . . . ?
C3 C4 C5 C6 -178.21(17) . . . . ?
C7 C5 C6 O3 -157.5(2) . . . . ?
C4 C5 C6 O3 21.6(3) . . . . ?
C7 C5 C6 O4 23.1(3) . . . . ?
C4 C5 C6 O4 -157.83(18) . . . . ?
C4 C5 C7 F4 -179.33(17) . . . . ?
C6 C5 C7 F4 -0.2(3) . . . . ?
C4 C5 C7 C8 0.6(3) . . . . ?
C6 C5 C7 C8 179.70(18) . . . . ?
C3 C2 C8 F3 -178.46(16) . . . . ?
C1 C2 C8 F3 -0.9(3) . . . . ?
C3 C2 C8 C7 -0.4(3) . . . . ?
C1 C2 C8 C7 177.15(17) . . . . ?
F4 C7 C8 F3 -2.8(3) . . . . ?
C5 C7 C8 F3 177.27(17) . . . . ?
F4 C7 C8 C2 179.05(16) . . . . ?
C5 C7 C8 C2 -0.9(3) . . . . ?
N1 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 N2 0.4(3) . . . . ?
C10 C9 N1 N2 0.0(3) . . . . ?
C10 C11 N2 N1 -0.5(3) . . . . ?
C9 N1 N2 C11 0.3(3) . . . . ?

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
O4 H4 O1 0.87(3) 1.73(3) 2.597(2) 177(3) 1_556
N2 H2 O2 0.90(3) 1.80(3) 2.698(3) 170(2) .
N1 H1 O1 0.92(3) 1.81(3) 2.722(2) 173(3) 3_566
C11 H11 O3 0.93 2.52 3.114(3) 121.5 3_667
C11 H11 F2 0.93 2.49 3.063(3) 119.8 2_656
C9 H9 F1 0.93 2.57 3.049(3) 112.2 3_566

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.170

