# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_exp_3042
_database_code_depnum_ccdc_archive 'CCDC 1062275'
loop_
_audit_author_name
_audit_author_address
'Jifeng Chen'
;beijing institute of technology
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H6 F2 N4 O6'
_chemical_formula_weight         244.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.7184(4)
_cell_length_b                   8.2861(10)
_cell_length_c                   9.6182(7)
_cell_angle_alpha                100.379(8)
_cell_angle_beta                 103.018(6)
_cell_angle_gamma                92.979(8)
_cell_volume                     434.72(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1495
_cell_measurement_theta_min      2.9993
_cell_measurement_theta_max      29.2656

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.908
_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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2903
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.004
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1698
_reflns_number_gt                1519
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.0661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1698
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.46478(17) 0.73181(12) 0.02409(9) 0.0254(3) Uani 1 1 d . . . . .
F2 F 0.75553(18) 0.92304(12) 0.05598(10) 0.0254(3) Uani 1 1 d . . . . .
O3 O 0.33423(19) 0.80071(13) 0.49114(10) 0.0165(3) Uani 1 1 d . . . . .
O5 O 0.9264(2) 0.66336(14) 0.81747(11) 0.0211(3) Uani 1 1 d . . . . .
O6 O 0.6036(2) 0.48897(14) 0.75916(11) 0.0217(3) Uani 1 1 d . . . . .
O4 O 0.25424(19) 0.56241(13) 0.54852(11) 0.0187(3) Uani 1 1 d . . . . .
O2 O 0.7398(2) 1.00187(13) 0.75244(11) 0.0196(3) Uani 1 1 d . . . . .
N2 N 0.7502(2) 0.87370(15) 0.66932(13) 0.0141(3) Uani 1 1 d . . . . .
N3 N 0.3869(2) 0.69260(15) 0.56814(12) 0.0136(3) Uani 1 1 d . . . . .
O1 O 0.8802(2) 0.85731(14) 0.58357(11) 0.0208(3) Uani 1 1 d . . . . .
N4 N 0.7123(2) 0.62008(16) 0.75257(13) 0.0158(3) Uani 1 1 d . . . . .
N1 N 0.8716(2) 0.68942(16) 0.28531(12) 0.0150(3) Uani 1 1 d . . . . .
H1A H 1.017103 0.724228 0.342914 0.018 Uiso 1 1 calc R U . . .
H1B H 0.807762 0.602237 0.310795 0.018 Uiso 1 1 calc R U . . .
C1 C 0.8668(3) 0.6636(2) 0.12443(15) 0.0172(3) Uani 1 1 d . . . . .
H1C H 0.801364 0.553971 0.070550 0.021 Uiso 1 1 calc R U . . .
H1D H 1.020102 0.694696 0.104611 0.021 Uiso 1 1 calc R U . . .
C4 C 0.5982(3) 0.72864(18) 0.67297(15) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.6875(3) 0.79326(19) 0.10878(15) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.7045(3) 0.82571(18) 0.27159(15) 0.0150(3) Uani 1 1 d . . . . .
H3A H 0.552654 0.802581 0.296461 0.018 Uiso 1 1 calc R U . . .
H3B H 0.780414 0.934244 0.322249 0.018 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0197(5) 0.0289(6) 0.0206(5) 0.0019(4) -0.0073(4) 0.0027(4)
F2 0.0309(6) 0.0245(5) 0.0257(5) 0.0155(4) 0.0076(4) 0.0049(4)
O3 0.0146(6) 0.0191(6) 0.0159(5) 0.0082(4) 0.0001(4) 0.0021(4)
O5 0.0169(6) 0.0222(6) 0.0198(5) 0.0060(5) -0.0056(5) 0.0007(5)
O6 0.0245(6) 0.0166(6) 0.0230(6) 0.0087(5) 0.0010(5) -0.0028(5)
O4 0.0166(6) 0.0185(6) 0.0190(5) 0.0054(4) 0.0003(4) -0.0057(5)
O2 0.0234(6) 0.0137(6) 0.0183(5) -0.0001(4) 0.0004(5) 0.0029(5)
N2 0.0124(6) 0.0157(7) 0.0118(6) 0.0039(5) -0.0026(5) -0.0001(5)
N3 0.0133(6) 0.0152(7) 0.0120(6) 0.0027(5) 0.0024(5) 0.0009(5)
O1 0.0188(6) 0.0264(7) 0.0175(5) 0.0035(5) 0.0066(5) -0.0024(5)
N4 0.0174(7) 0.0168(7) 0.0120(6) 0.0034(5) 0.0009(5) 0.0007(5)
N1 0.0134(6) 0.0180(7) 0.0124(6) 0.0045(5) -0.0004(5) 0.0008(5)
C1 0.0200(8) 0.0200(8) 0.0105(7) 0.0024(6) 0.0017(6) 0.0033(7)
C4 0.0144(8) 0.0146(8) 0.0145(7) 0.0041(6) -0.0004(6) 0.0003(6)
C2 0.0167(8) 0.0171(8) 0.0154(7) 0.0050(6) -0.0016(6) -0.0001(6)
C3 0.0143(7) 0.0134(8) 0.0163(7) 0.0018(6) 0.0022(6) 0.0015(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.3641(18) . ?
F2 C2 1.3446(18) . ?
O3 N3 1.2682(15) . ?
O5 N4 1.2436(17) . ?
O6 N4 1.2420(17) . ?
O4 N3 1.2458(17) . ?
O2 N2 1.2218(16) . ?
N2 O1 1.2234(17) . ?
N2 C4 1.457(2) . ?
N3 C4 1.3678(19) . ?
N4 C4 1.3804(18) . ?
N1 C1 1.5171(17) . ?
N1 C3 1.5214(18) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C1 C2 1.527(2) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 C3 1.5201(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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 N2 O1 124.98(13) . . ?
O2 N2 C4 117.75(13) . . ?
O1 N2 C4 117.27(12) . . ?
O4 N3 O3 121.81(11) . . ?
O4 N3 C4 122.66(12) . . ?
O3 N3 C4 115.53(12) . . ?
O6 N4 O5 123.04(11) . . ?
O6 N4 C4 121.12(12) . . ?
O5 N4 C4 115.84(13) . . ?
C1 N1 C3 91.11(10) . . ?
C1 N1 H1A 113.4 . . ?
C3 N1 H1A 113.4 . . ?
C1 N1 H1B 113.4 . . ?
C3 N1 H1B 113.4 . . ?
H1A N1 H1B 110.7 . . ?
N1 C1 C2 88.92(11) . . ?
N1 C1 H1C 113.8 . . ?
C2 C1 H1C 113.8 . . ?
N1 C1 H1D 113.8 . . ?
C2 C1 H1D 113.8 . . ?
H1C C1 H1D 111.1 . . ?
N3 C4 N4 125.78(14) . . ?
N3 C4 N2 116.23(12) . . ?
N4 C4 N2 115.22(12) . . ?
F2 C2 F1 106.17(11) . . ?
F2 C2 C3 115.63(13) . . ?
F1 C2 C3 114.68(13) . . ?
F2 C2 C1 115.76(13) . . ?
F1 C2 C1 113.71(13) . . ?
C3 C2 C1 90.78(10) . . ?
C2 C3 N1 89.02(10) . . ?
C2 C3 H3A 113.8 . . ?
N1 C3 H3A 113.8 . . ?
C2 C3 H3B 113.8 . . ?
N1 C3 H3B 113.8 . . ?
H3A C3 H3B 111.0 . . ?

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
C3 N1 C1 C2 -3.10(12) . . . . ?
O4 N3 C4 N4 11.4(2) . . . . ?
O3 N3 C4 N4 -168.45(13) . . . . ?
O4 N3 C4 N2 171.53(12) . . . . ?
O3 N3 C4 N2 -8.27(19) . . . . ?
O6 N4 C4 N3 -16.9(2) . . . . ?
O5 N4 C4 N3 164.03(14) . . . . ?
O6 N4 C4 N2 -177.26(13) . . . . ?
O5 N4 C4 N2 3.67(19) . . . . ?
O2 N2 C4 N3 98.73(15) . . . . ?
O1 N2 C4 N3 -81.74(16) . . . . ?
O2 N2 C4 N4 -98.97(15) . . . . ?
O1 N2 C4 N4 80.56(15) . . . . ?
N1 C1 C2 F2 122.23(13) . . . . ?
N1 C1 C2 F1 -114.42(13) . . . . ?
N1 C1 C2 C3 3.10(12) . . . . ?
F2 C2 C3 N1 -122.34(13) . . . . ?
F1 C2 C3 N1 113.58(13) . . . . ?
C1 C2 C3 N1 -3.09(12) . . . . ?
C1 N1 C3 C2 3.11(12) . . . . ?

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
_geom_hbond_publ_flag
N1 H1A O3 0.89 2.03 2.9150(16) 174.3 1_655 yes
N1 H1B O6 0.89 2.34 2.9301(18) 123.8 2_666 yes
N1 H1B O4 0.89 2.16 2.9985(16) 157.7 2_666 yes
C3 H3A O3 0.97 2.48 3.3335(19) 147.3 . yes
C3 H3A O6 0.97 2.45 3.0003(19) 115.4 2_666 yes
C3 H3A O2 0.97 2.42 2.9634(17) 115.2 2_676 yes
C3 H3B O1 0.97 2.42 3.320(2) 153.8 2_776 yes

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.060

_shelx_res_file                  
;
TITL exp_3042 in P-1 #2
    exp_3042.res
    created by SHELXL-2018/3 at 16:51:49 on 15-Aug-2019
CELL 0.71073 5.718429 8.286133 9.618158 100.379 103.018 92.9788
ZERR 2 0.000449 0.000964 0.000691 0.0077 0.0064 0.0078
LATT 1

SFAC C H F N O
UNIT 8 12 4 8 12
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!

L.S. 4
PLAN  4
SIZE 0.5 0.55 0.5

bond $H
conf
EQIV $1 x+1, y, z
HTAB N1 O3_$1
EQIV $2 -x+1, -y+1, -z+1
HTAB N1 O6_$2
HTAB N1 O4_$2
HTAB C3 O3
HTAB C3 O6_$2
EQIV $3 -x+1, -y+2, -z+1
HTAB C3 O2_$3
EQIV $4 -x+2, -y+2, -z+1
HTAB C3 O1_$4
fmap 2
acta
OMIT -2 52

WGHT    0.043800    0.066100
FVAR      12.51456
F1    3    0.464783    0.731809    0.024089    11.00000    0.01973    0.02888 =
         0.02058    0.00188   -0.00733    0.00269
F2    3    0.755532    0.923044    0.055983    11.00000    0.03089    0.02448 =
         0.02566    0.01554    0.00764    0.00488
O3    5    0.334231    0.800713    0.491137    11.00000    0.01460    0.01915 =
         0.01588    0.00825    0.00011    0.00208
O5    5    0.926398    0.663358    0.817467    11.00000    0.01691    0.02222 =
         0.01979    0.00600   -0.00562    0.00074
O6    5    0.603645    0.488974    0.759156    11.00000    0.02445    0.01660 =
         0.02303    0.00870    0.00098   -0.00278
O4    5    0.254237    0.562413    0.548522    11.00000    0.01659    0.01854 =
         0.01901    0.00535    0.00030   -0.00570
O2    5    0.739791    1.001866    0.752443    11.00000    0.02344    0.01369 =
         0.01829   -0.00011    0.00040    0.00290
N2    4    0.750248    0.873696    0.669318    11.00000    0.01242    0.01567 =
         0.01177    0.00387   -0.00260   -0.00013
N3    4    0.386893    0.692605    0.568136    11.00000    0.01328    0.01521 =
         0.01198    0.00272    0.00244    0.00086
O1    5    0.880166    0.857305    0.583569    11.00000    0.01876    0.02641 =
         0.01752    0.00354    0.00660   -0.00241
N4    4    0.712303    0.620078    0.752575    11.00000    0.01740    0.01677 =
         0.01201    0.00340    0.00088    0.00071
N1    4    0.871622    0.689423    0.285306    11.00000    0.01342    0.01802 =
         0.01237    0.00448   -0.00042    0.00078
AFIX  23
H1A   2    1.017103    0.724228    0.342914    11.00000   -1.20000
H1B   2    0.807762    0.602237    0.310795    11.00000   -1.20000
AFIX   0
C1    1    0.866799    0.663558    0.124428    11.00000    0.01999    0.02000 =
         0.01054    0.00240    0.00167    0.00334
AFIX  23
H1C   2    0.801364    0.553971    0.070550    11.00000   -1.20000
H1D   2    1.020102    0.694696    0.104611    11.00000   -1.20000
AFIX   0

C4    1    0.598177    0.728640    0.672968    11.00000    0.01440    0.01464 =
         0.01453    0.00411   -0.00042    0.00033
C2    1    0.687512    0.793261    0.108784    11.00000    0.01671    0.01711 =
         0.01542    0.00500   -0.00162   -0.00012
C3    1    0.704516    0.825705    0.271589    11.00000    0.01430    0.01336 =
         0.01626    0.00179    0.00217    0.00149
AFIX  23
H3A   2    0.552654    0.802581    0.296461    11.00000   -1.20000
H3B   2    0.780414    0.934244    0.322249    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_3042 in P-1 #2
REM wR2 = 0.089292, GooF = S = 1.06892, Restrained GooF = 1.06892 for all data
REM R1 = 0.034510 for 1519 Fo > 4sig(Fo) and 0.038736 for all 1698 data
REM 145 parameters refined using 0 restraints

END

WGHT      0.0439      0.0673

REM Highest difference peak  0.258,  deepest hole -0.277,  1-sigma level  0.060
Q1    1   0.6817  0.8174  0.1877  11.00000  0.05    0.26
Q2    1   0.7691  0.7268  0.0954  11.00000  0.05    0.23
Q3    1   0.9996  0.5449  0.8009  11.00000  0.05    0.21
Q4    1   0.9169  0.5362  0.0924  11.00000  0.05    0.18
;
_shelx_res_checksum              59902
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_3232
_database_code_depnum_ccdc_archive 'CCDC 1434944'
loop_
_audit_author_name
_audit_author_address
'Jifeng Chen'
;beijing institute of technology
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 Cl F2 N O4'
_chemical_formula_weight         193.54

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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   12.1852(8)
_cell_length_b                   7.0366(3)
_cell_length_c                   7.5024(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     643.27(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    864
_cell_measurement_theta_min      3.1820
_cell_measurement_theta_max      29.4324

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.998
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.602
_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      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2483
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.189
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             687
_reflns_number_gt                635
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+13.3715P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         687
_refine_ls_number_parameters     74
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.1904
_refine_ls_wR_factor_gt          0.1893
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4174(4) 0.250000 -0.6300(8) 0.0242(15) Uani 1 2 d S T P . .
F2 F 0.4526(5) 0.250000 -0.9158(8) 0.0261(15) Uani 1 2 d S T P . .
N1 N 0.6733(6) 0.250000 -0.7310(11) 0.025(2) Uani 1 2 d S T P . .
H1C H 0.715522 0.250000 -0.830854 0.030 Uiso 1 2 d R U P . .
H1D H 0.715680 0.250000 -0.631302 0.030 Uiso 1 2 d R U P . .
C1 C 0.5863(5) 0.0966(9) -0.7302(9) 0.0187(15) Uani 1 1 d . . . . .
H1A H 0.581168 0.026303 -0.616166 0.022 Uiso 1 1 calc R U . . .
H1B H 0.591077 0.008153 -0.832509 0.022 Uiso 1 1 calc R U . . .
C2 C 0.5000(7) 0.250000 -0.7519(12) 0.0132(18) Uani 1 2 d S T P . .
Cl1 Cl 0.67736(17) 0.250000 -0.2333(3) 0.0113(6) Uani 1 2 d S TU P . .
O3 O 0.7591(5) 0.250000 -0.3742(8) 0.0178(15) Uani 1 2 d S TU P A .
O1 O 0.5710(6) 0.2103(12) -0.3086(11) 0.016(3) Uani 0.5 1 d . U P A -1
O2 O 0.6785(10) 0.4336(18) -0.1521(17) 0.019(3) Uani 0.5 1 d . U P A -1
O4 O 0.7045(10) 0.1131(19) -0.0988(15) 0.018(3) Uani 0.5 1 d . U P A -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.010(3) 0.040(4) 0.022(3) 0.000 0.007(2) 0.000
F2 0.019(3) 0.042(4) 0.017(3) 0.000 -0.007(2) 0.000
N1 0.013(4) 0.047(6) 0.015(4) 0.000 -0.003(3) 0.000
C1 0.026(3) 0.014(3) 0.016(3) -0.003(3) 0.003(3) 0.008(3)
C2 0.013(4) 0.014(4) 0.013(4) 0.000 0.002(3) 0.000
Cl1 0.0127(10) 0.0111(10) 0.0101(10) 0.000 0.0001(8) 0.000
O3 0.019(3) 0.023(3) 0.012(3) 0.000 0.003(3) 0.000
O1 0.014(3) 0.017(7) 0.018(4) -0.002(3) -0.005(3) 0.001(3)
O2 0.024(6) 0.010(5) 0.021(6) -0.009(4) 0.004(5) 0.003(4)
O4 0.020(5) 0.021(6) 0.014(6) 0.006(4) -0.004(4) 0.008(5)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.360(10) . ?
F2 C2 1.359(11) . ?
N1 C1 1.513(8) . ?
N1 C1 1.513(8) 8_565 ?
N1 H1C 0.9090 . ?
N1 H1D 0.9089 . ?
C1 C2 1.516(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
Cl1 O2 1.429(12) . ?
Cl1 O4 1.433(13) . ?
Cl1 O1 1.441(8) . ?
Cl1 O3 1.453(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
C1 N1 C1 91.1(6) . 8_565 ?
C1 N1 H1C 113.6 . . ?
C1 N1 H1C 113.6 8_565 . ?
C1 N1 H1D 113.3 . . ?
C1 N1 H1D 113.3 8_565 . ?
H1C N1 H1D 110.9 . . ?
N1 C1 C2 88.7(5) . . ?
N1 C1 H1A 113.9 . . ?
C2 C1 H1A 113.9 . . ?
N1 C1 H1B 113.9 . . ?
C2 C1 H1B 113.9 . . ?
H1A C1 H1B 111.1 . . ?
F2 C2 F1 107.1(7) . . ?
F2 C2 C1 113.1(5) . 8_565 ?
F1 C2 C1 116.2(5) . 8_565 ?
F2 C2 C1 113.1(5) . . ?
F1 C2 C1 116.2(5) . . ?
C1 C2 C1 90.8(7) 8_565 . ?
O2 Cl1 O4 107.8(8) . . ?
O2 Cl1 O1 110.6(6) . . ?
O4 Cl1 O1 110.7(6) . . ?
O2 Cl1 O3 107.7(5) . . ?
O4 Cl1 O3 110.7(5) . . ?
O1 Cl1 O3 109.4(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
C1 N1 C1 C2 6.4(7) 8_565 . . . ?
N1 C1 C2 F2 109.2(6) . . . . ?
N1 C1 C2 F1 -126.3(6) . . . . ?
N1 C1 C2 C1 -6.4(7) . . . 8_565 ?

_refine_diff_density_max         0.658
_refine_diff_density_min         -0.992
_refine_diff_density_rms         0.155

_shelx_res_file                  
;
TITL exp_3232         P 21 21 21   R = 0.03 New:Pnma
    exp_3232.res
    created by SHELXL-2018/3 at 17:32:44 on 20-Aug-2019
CELL  0.71073   12.1852    7.0366    7.5024    90.000    90.000    90.000
ZERR        4    0.0008    0.0003    0.0005     0.000     0.000     0.000
LATT   1
SYMM     0.50000 - X ,            - Y ,    0.50000 + Z
SYMM     0.50000 + X ,    0.50000 - Y ,    0.50000 - Z
SYMM             - X ,    0.50000 + Y ,            - Z
SFAC  C  H Cl  F  N  O
UNIT    12   24   4   8   4  16
OMIT 3 2 3
OMIT 1 3 1
OMIT 3 1 1
LIST 4
TEMP  -172
L.S. 5
FMAP 2
PLAN -20
ACTA
BOND $H
omit -3 52
CONF
WGHT    0.020000   13.371490
EXTI    0.011262
FVAR       6.70227
RESI 0
F1    4    0.417428    0.250000   -0.630014    10.50000    0.01047    0.03977 =
         0.02237    0.00000    0.00663    0.00000
F2    4    0.452646    0.250000   -0.915845    10.50000    0.01889    0.04207 =
         0.01733    0.00000   -0.00675    0.00000
N1    5    0.673292    0.250000   -0.730984    10.50000    0.01297    0.04689 =
         0.01524    0.00000   -0.00256    0.00000
AFIX   3
H1C   2    0.715522    0.250000   -0.830854    10.50000   -1.20000
H1D   2    0.715680    0.250000   -0.631302    10.50000   -1.20000
AFIX   0
C1    1    0.586338    0.096590   -0.730168    11.00000    0.02569    0.01397 =
         0.01642   -0.00322    0.00297    0.00845
AFIX  23
H1A   2    0.581168    0.026303   -0.616166    11.00000   -1.20000
H1B   2    0.591077    0.008153   -0.832509    11.00000   -1.20000
AFIX   0
C2    1    0.500023    0.250000   -0.751919    10.50000    0.01301    0.01372 =
         0.01287    0.00000    0.00179    0.00000
simu 0.01 0.02 2.5 cl1 > O4
CL1   3    0.677359    0.250000   -0.233287    10.50000    0.01266    0.01108 =
         0.01014    0.00000    0.00010    0.00000
O3    6    0.759135    0.250000   -0.374189    10.50000    0.01854    0.02261 =
         0.01231    0.00000    0.00288    0.00000
part -1 10.5
O1    6    0.571007    0.210329   -0.308622    10.50000    0.01413    0.01737 =
         0.01784   -0.00224   -0.00524    0.00083
O2    6    0.678519    0.433649   -0.152062    10.50000    0.02394    0.01041 =
         0.02141   -0.00886    0.00429    0.00250
O4    6    0.704496    0.113139   -0.098826    10.50000    0.01980    0.02068 =
         0.01355    0.00578   -0.00439    0.00818
part 0

HKLF 4 1 0.0000 0.0000 1.0000 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000




REM  exp_3232         P 21 21 21   R = 0.03 New:Pnma
REM wR2 = 0.1904, GooF = S = 1.147, Restrained GooF = 1.100 for all data
REM R1 = 0.0781 for 635 Fo > 4sig(Fo) and 0.0813 for all 687 data
REM 74 parameters refined using 60 restraints

END

WGHT      0.0000      8.5686

REM Highest difference peak  0.658,  deepest hole -0.992,  1-sigma level  0.155
Q1    1   0.4679  0.2500 -1.0548  10.50000  0.05    0.66
Q2    1   0.6055  0.2500 -1.1206  10.50000  0.05    0.58
Q3    1   0.3263  0.2500 -0.6394  10.50000  0.05    0.54
Q4    1   0.5642  0.2500 -0.9690  10.50000  0.05    0.51
Q5    1   0.4300  0.2500 -0.3486  10.50000  0.05    0.50
Q6    1   0.7573  0.1670 -1.0427  11.00000  0.05    0.48
Q7    1   0.2870  0.1772 -0.4466  11.00000  0.05    0.47
Q8    1   0.5587  0.1569 -0.4966  11.00000  0.05    0.46
Q9    1   0.7937  0.1168 -0.1785  11.00000  0.05    0.45
Q10   1   0.7057  0.2500 -0.4490  10.50000  0.05    0.43
Q11   1   0.6404  0.0391 -0.5875  11.00000  0.05    0.42
Q12   1   0.3081  0.1478 -0.6895  11.00000  0.05    0.41
Q13   1   0.4175  0.1619 -0.7178  11.00000  0.05    0.41
Q14   1   0.7334  0.2500 -0.4950  10.50000  0.05    0.40
Q15   1   0.7132 -0.0182 -0.8511  11.00000  0.05    0.37
Q16   1   0.7536  0.2500 -0.3233  10.50000  0.05    0.37
Q17   1   0.5692  0.0918 -0.1121  11.00000  0.05    0.37
Q18   1   0.7419  0.0642 -0.6068  11.00000  0.05    0.35
Q19   1   0.5115  0.2003 -0.6371  11.00000  0.05    0.35
Q20   1   0.5378 -0.1398 -0.7166  11.00000  0.05    0.35
;
_shelx_res_checksum              13398
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_3231
_database_code_depnum_ccdc_archive 'CCDC 1434943'
loop_
_audit_author_name
_audit_author_address
'Jifeng Chen'
;beijing institute of technology
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 F2 N2 O3'
_chemical_formula_weight         156.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.5333(8)
_cell_length_b                   6.1726(9)
_cell_length_c                   9.2437(16)
_cell_angle_alpha                91.249(13)
_cell_angle_beta                 106.658(14)
_cell_angle_gamma                92.337(12)
_cell_volume                     302.03(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    707
_cell_measurement_theta_min      3.2996
_cell_measurement_theta_max      29.3828

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_F_000             160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.973
_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      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1910
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.305
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1184
_reflns_number_gt                999
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+0.0423P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1184
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4130(2) 0.74495(18) 0.95768(13) 0.0260(3) Uani 1 1 d . . . . .
O2 O 0.2357(2) 0.7547(2) 0.42008(15) 0.0200(3) Uani 1 1 d . . . . .
O3 O 0.0949(2) 0.7070(2) 0.61362(14) 0.0158(3) Uani 1 1 d . . . . .
N2 N 0.0530(3) 0.7524(2) 0.47605(17) 0.0136(4) Uani 1 1 d . . . . .
F2 F 0.8215(2) 0.75028(18) 1.03488(13) 0.0281(3) Uani 1 1 d . . . . .
O1 O -0.1619(2) 0.7939(2) 0.39950(15) 0.0199(3) Uani 1 1 d . . . . .
N1 N 0.6463(3) 0.7341(2) 0.68301(17) 0.0162(4) Uani 1 1 d . . . . .
H1A H 0.795215 0.734028 0.659571 0.019 Uiso 1 1 calc R U . . .
H1B H 0.513490 0.729682 0.597683 0.019 Uiso 1 1 calc R U . . .
C2 C 0.6224(3) 0.7436(3) 0.9083(2) 0.0163(4) Uani 1 1 d . . . . .
C1 C 0.6230(3) 0.5632(3) 0.7942(2) 0.0160(4) Uani 1 1 d . . . . .
H1C H 0.770729 0.471720 0.825209 0.019 Uiso 1 1 calc R U . . .
H1D H 0.463459 0.473029 0.761691 0.019 Uiso 1 1 calc R U . . .
C3 C 0.6367(4) 0.9141(3) 0.7948(2) 0.0171(4) Uani 1 1 d . . . . .
H3A H 0.484062 0.999682 0.762698 0.021 Uiso 1 1 calc R U . . .
H3B H 0.791769 1.010136 0.826237 0.021 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0348(7) 0.0257(7) 0.0263(7) 0.0008(5) 0.0225(6) 0.0027(5)
O2 0.0195(7) 0.0264(8) 0.0173(7) 0.0007(6) 0.0109(6) -0.0006(6)
O3 0.0164(7) 0.0202(7) 0.0118(7) 0.0026(5) 0.0052(5) 0.0018(5)
N2 0.0147(8) 0.0117(8) 0.0148(8) -0.0005(6) 0.0050(7) 0.0004(6)
F2 0.0349(7) 0.0275(7) 0.0141(7) 0.0007(5) -0.0052(5) -0.0017(5)
O1 0.0150(7) 0.0213(7) 0.0195(8) 0.0012(6) -0.0015(6) 0.0036(6)
N1 0.0125(8) 0.0243(9) 0.0120(8) 0.0019(7) 0.0038(6) 0.0000(7)
C2 0.0170(9) 0.0207(10) 0.0116(10) 0.0014(8) 0.0048(8) 0.0008(8)
C1 0.0174(9) 0.0166(9) 0.0149(10) 0.0021(8) 0.0057(8) 0.0022(7)
C3 0.0194(10) 0.0172(9) 0.0147(10) -0.0011(8) 0.0052(8) -0.0004(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.362(2) . ?
O2 N2 1.2607(18) . ?
O3 N2 1.2654(19) . ?
N2 O1 1.2371(19) . ?
F2 C2 1.357(2) . ?
N1 C3 1.514(2) . ?
N1 C1 1.516(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
C2 C3 1.517(3) . ?
C2 C1 1.518(3) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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 N2 O2 121.31(15) . . ?
O1 N2 O3 120.50(14) . . ?
O2 N2 O3 118.19(15) . . ?
C3 N1 C1 91.16(13) . . ?
C3 N1 H1A 113.4 . . ?
C1 N1 H1A 113.4 . . ?
C3 N1 H1B 113.4 . . ?
C1 N1 H1B 113.4 . . ?
H1A N1 H1B 110.7 . . ?
F2 C2 F1 105.60(14) . . ?
F2 C2 C3 114.86(16) . . ?
F1 C2 C3 115.24(15) . . ?
F2 C2 C1 114.85(15) . . ?
F1 C2 C1 115.40(16) . . ?
C3 C2 C1 90.94(14) . . ?
N1 C1 C2 88.88(13) . . ?
N1 C1 H1C 113.8 . . ?
C2 C1 H1C 113.8 . . ?
N1 C1 H1D 113.8 . . ?
C2 C1 H1D 113.8 . . ?
H1C C1 H1D 111.1 . . ?
N1 C3 C2 88.96(13) . . ?
N1 C3 H3A 113.8 . . ?
C2 C3 H3A 113.8 . . ?
N1 C3 H3B 113.8 . . ?
C2 C3 H3B 113.8 . . ?
H3A C3 H3B 111.0 . . ?

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
C3 N1 C1 C2 -1.82(14) . . . . ?
F2 C2 C1 N1 -116.28(15) . . . . ?
F1 C2 C1 N1 120.50(16) . . . . ?
C3 C2 C1 N1 1.81(13) . . . . ?
C1 N1 C3 C2 1.82(14) . . . . ?
F2 C2 C3 N1 116.27(15) . . . . ?
F1 C2 C3 N1 -120.63(16) . . . . ?
C1 C2 C3 N1 -1.82(13) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.077

_shelx_res_file                  
;
TITL exp_3231 in P-1 #2
    exp_3231.res
    created by SHELXL-2018/3 at 16:53:22 on 15-Aug-2019
CELL 0.71073 5.533298 6.172559 9.243666 91.2485 106.6579 92.3373
ZERR 2 0.000814 0.000856 0.00156 0.0128 0.0141 0.0116
LATT 1

SFAC C H F N O
UNIT 6 12 4 4 6
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!

L.S. 4
PLAN  5
SIZE 0.3 0.34 0.15
TEMP -171.65

bond $H
conf
htab
fmap 2
acta
OMIT -2 52

WGHT    0.042300    0.042300
FVAR      14.91746
F1    3    0.412972    0.744952    0.957679    11.00000    0.03479    0.02574 =
         0.02625    0.00080    0.02252    0.00268
O2    5    0.235705    0.754716    0.420083    11.00000    0.01954    0.02645 =
         0.01726    0.00066    0.01092   -0.00062
O3    5    0.094910    0.706974    0.613624    11.00000    0.01641    0.02017 =
         0.01181    0.00261    0.00522    0.00181
N2    4    0.052964    0.752351    0.476045    11.00000    0.01467    0.01170 =
         0.01482   -0.00050    0.00501    0.00038
F2    3    0.821536    0.750283    1.034875    11.00000    0.03486    0.02745 =
         0.01410    0.00072   -0.00524   -0.00170
O1    5   -0.161903    0.793874    0.399497    11.00000    0.01504    0.02125 =
         0.01953    0.00118   -0.00146    0.00357
N1    4    0.646319    0.734127    0.683009    11.00000    0.01246    0.02434 =
         0.01202    0.00190    0.00378    0.00001
AFIX  23
H1A   2    0.795215    0.734028    0.659571    11.00000   -1.20000
H1B   2    0.513490    0.729682    0.597683    11.00000   -1.20000
AFIX   0
C2    1    0.622397    0.743624    0.908284    11.00000    0.01699    0.02065 =
         0.01164    0.00137    0.00482    0.00084
C1    1    0.622984    0.563249    0.794174    11.00000    0.01741    0.01657 =
         0.01489    0.00213    0.00567    0.00215
AFIX  23
H1C   2    0.770729    0.471720    0.825209    11.00000   -1.20000
H1D   2    0.463459    0.473029    0.761691    11.00000   -1.20000
AFIX   0
C3    1    0.636706    0.914096    0.794824    11.00000    0.01943    0.01716 =
         0.01472   -0.00114    0.00524   -0.00040
AFIX  23
H3A   2    0.484062    0.999682    0.762698    11.00000   -1.20000
H3B   2    0.791769    1.010136    0.826237    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_3231 in P-1 #2
REM wR2 = 0.098527, GooF = S = 1.12307, Restrained GooF = 1.12307 for all data
REM R1 = 0.038251 for 999 Fo > 4sig(Fo) and 0.046691 for all 1184 data
REM 91 parameters refined using 0 restraints

END

WGHT      0.0423      0.0423

REM Instructions for potential hydrogen bonds
EQIV $1 x+1, y, z
HTAB N1 O3_$1
HTAB N1 N2_$1
HTAB N1 O1_$1
HTAB N1 O2
HTAB N1 O3
HTAB N1 N2
EQIV $2 -x, -y+1, -z+1
HTAB C1 O1_$2
EQIV $3 -x, -y+2, -z+1
HTAB C3 O1_$3
EQIV $4 -x+2, -y+2, -z+2
HTAB C3 F2_$4

REM Highest difference peak  0.322,  deepest hole -0.320,  1-sigma level  0.077
Q1    1   0.8521  0.9771  1.0335  11.00000  0.05    0.32
Q2    1  -0.1833  0.6047  0.3998  11.00000  0.05    0.24
Q3    1  -0.1215  0.9931  0.4178  11.00000  0.05    0.24
Q4    1   0.1424  0.4931  0.6176  11.00000  0.05    0.23
Q5    1   0.3905  0.4941  0.5471  11.00000  0.05    0.23
;
_shelx_res_checksum              14609
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1434945'
loop_
_audit_author_name
_audit_author_address
'Jifeng Chen'
;beijing institute of technology
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 Cl F2 N'
_chemical_formula_weight         129.54

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.334(7)
_cell_length_b                   9.277(6)
_cell_length_c                   11.237(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1077.3(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1992
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      27.69

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.623
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.970
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6927
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.464
_diffrn_reflns_theta_max         27.706
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1263
_reflns_number_gt                1032
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.3639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1263
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.07974(10) 0.81482(14) 0.19260(9) 0.0369(3) Uani 1 1 d . . . . .
F2 F -0.05144(10) 0.58808(13) 0.22076(8) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.14168(12) 0.75299(13) 0.37851(11) 0.0124(3) Uani 1 1 d . . . . .
H1A H 0.183572 0.678733 0.414789 0.015 Uiso 1 1 d R U . . .
H1B H 0.173822 0.839133 0.403539 0.015 Uiso 1 1 d R U . . .
C1 C 0.13667(15) 0.73910(17) 0.24500(13) 0.0156(3) Uani 1 1 d . . . . .
H1C H 0.182832 0.653578 0.213790 0.019 Uiso 1 1 calc R U . . .
H1D H 0.162934 0.827588 0.202084 0.019 Uiso 1 1 calc R U . . .
C2 C -0.00815(15) 0.7195(2) 0.25416(13) 0.0182(3) Uani 1 1 d . . . . .
C3 C -0.00323(14) 0.74303(17) 0.38770(13) 0.0157(3) Uani 1 1 d . . . . .
H3A H -0.045225 0.833408 0.414220 0.019 Uiso 1 1 calc R U . . .
H3B H -0.034053 0.659616 0.434779 0.019 Uiso 1 1 calc R U . . .
Cl1 Cl 0.25070(3) 0.99514(3) 0.02393(3) 0.01298(14) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0199(5) 0.0603(9) 0.0305(6) 0.0180(6) -0.0083(4) 0.0083(5)
F2 0.0328(6) 0.0413(7) 0.0288(6) -0.0133(5) 0.0007(4) -0.0207(5)
N1 0.0133(6) 0.0117(7) 0.0123(6) -0.0012(4) -0.0016(5) -0.0002(4)
C1 0.0152(8) 0.0204(8) 0.0112(6) -0.0010(6) 0.0005(6) -0.0006(6)
C2 0.0147(8) 0.0251(9) 0.0147(7) 0.0009(6) -0.0029(6) -0.0020(6)
C3 0.0124(8) 0.0201(9) 0.0148(7) 0.0000(5) 0.0024(6) -0.0001(5)
Cl1 0.0149(2) 0.0116(2) 0.0124(2) 0.00009(12) 0.00005(12) -0.00096(12)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.345(2) . ?
F2 C2 1.351(2) . ?
N1 C3 1.504(2) . ?
N1 C1 1.507(2) . ?
N1 H1A 0.9101 . ?
N1 H1B 0.9100 . ?
C1 C2 1.511(2) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C2 C3 1.517(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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
C3 N1 C1 91.65(10) . . ?
C3 N1 H1A 113.4 . . ?
C1 N1 H1A 113.4 . . ?
C3 N1 H1B 113.3 . . ?
C1 N1 H1B 113.3 . . ?
H1A N1 H1B 110.7 . . ?
N1 C1 C2 88.66(11) . . ?
N1 C1 H1C 113.9 . . ?
C2 C1 H1C 113.9 . . ?
N1 C1 H1D 113.9 . . ?
C2 C1 H1D 113.9 . . ?
H1C C1 H1D 111.1 . . ?
F1 C2 F2 105.57(13) . . ?
F1 C2 C1 115.50(14) . . ?
F2 C2 C1 114.69(14) . . ?
F1 C2 C3 115.61(14) . . ?
F2 C2 C3 114.56(13) . . ?
C1 C2 C3 90.96(11) . . ?
N1 C3 C2 88.53(10) . . ?
N1 C3 H3A 113.9 . . ?
C2 C3 H3A 113.9 . . ?
N1 C3 H3B 113.9 . . ?
C2 C3 H3B 113.9 . . ?
H3A C3 H3B 111.1 . . ?

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
C3 N1 C1 C2 -3.39(12) . . . . ?
N1 C1 C2 F1 122.50(14) . . . . ?
N1 C1 C2 F2 -114.37(13) . . . . ?
N1 C1 C2 C3 3.36(12) . . . . ?
C1 N1 C3 C2 3.38(12) . . . . ?
F1 C2 C3 N1 -122.41(14) . . . . ?
F2 C2 C3 N1 114.47(13) . . . . ?
C1 C2 C3 N1 -3.37(12) . . . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.102

_shelx_res_file                  
;
TITL 1 in Pbca
    1.res
    created by SHELXL-2018/3 at 17:11:39 on 15-Aug-2019
CELL 0.71073 10.334 9.277 11.237 90 90 90
ZERR 8 0.007 0.006 0.007 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl F N
UNIT 24 48 8 16 8
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!

L.S. 20
PLAN  20
SIZE 0.21 0.19 0.05
TEMP -173
BOND $H
fmap 2
acta
MORE -1
CONF
OMIT 0 4 2
OMIT 4 1 0
REM <olex2.extras>
REM <HklSrc "%.\\1.hkl">
REM </olex2.extras>

WGHT    0.033800    0.363900
FVAR       0.15847
F1    4   -0.079742    0.814822    0.192603    11.00000    0.01986    0.06028 =
         0.03055    0.01800   -0.00829    0.00830
F2    4   -0.051438    0.588077    0.220757    11.00000    0.03276    0.04135 =
         0.02880   -0.01327    0.00069   -0.02071
N1    5    0.141682    0.752993    0.378509    11.00000    0.01328    0.01172 =
         0.01228   -0.00116   -0.00163   -0.00017
AFIX   3
H1A   2    0.183572    0.678733    0.414789    11.00000   -1.20000
H1B   2    0.173822    0.839133    0.403539    11.00000   -1.20000
AFIX   0
C1    1    0.136667    0.739103    0.245001    11.00000    0.01520    0.02041 =
         0.01119   -0.00097    0.00051   -0.00055
AFIX  23
H1C   2    0.182832    0.653578    0.213790    11.00000   -1.20000
H1D   2    0.162934    0.827588    0.202084    11.00000   -1.20000
AFIX   0
C2    1   -0.008147    0.719459    0.254156    11.00000    0.01472    0.02509 =
         0.01475    0.00090   -0.00287   -0.00197
C3    1   -0.003233    0.743029    0.387701    11.00000    0.01237    0.02006 =
         0.01480    0.00001    0.00237   -0.00009
AFIX  23
H3A   2   -0.045225    0.833408    0.414220    11.00000   -1.20000
H3B   2   -0.034053    0.659616    0.434779    11.00000   -1.20000
AFIX   0

CL1   3    0.250696    0.995136    0.023934    11.00000    0.01488    0.01165 =
         0.01243    0.00009    0.00005   -0.00096
HKLF 4 1 0 -1 0 0 0 1 -1 0 0




REM  1 in Pbca
REM wR2 = 0.082559, GooF = S = 1.06905, Restrained GooF = 1.06905 for all data
REM R1 = 0.032535 for 1032 Fo > 4sig(Fo) and 0.045317 for all 1263 data
REM 64 parameters refined using 0 restraints

END

WGHT      0.0338      0.3639

REM Highest difference peak  0.435,  deepest hole -0.378,  1-sigma level  0.102
Q1    1   0.2448  0.8747  0.2770  11.00000  0.05    0.44
Q2    1   0.0607  0.7366  0.2347  11.00000  0.05    0.42
Q3    1   0.2588  0.7544  0.2777  11.00000  0.05    0.38
Q4    1  -0.0365  0.8851  0.1899  11.00000  0.05    0.36
Q5    1   0.3023  0.9350  0.2299  11.00000  0.05    0.32
Q6    1  -0.0277  0.7328  0.3224  11.00000  0.05    0.31
Q7    1   0.2048  0.4989  0.2821  11.00000  0.05    0.31
Q8    1  -0.1902  0.4972  0.2116  11.00000  0.05    0.30
Q9    1   0.1884  0.9284  0.0275  11.00000  0.05    0.29
Q10   1   0.2554  0.8023  0.2154  11.00000  0.05    0.28
Q11   1  -0.0778  0.6663  0.1929  11.00000  0.05    0.28
Q12   1   0.3163  0.9980 -0.0381  11.00000  0.05    0.27
Q13   1   0.1841  0.9979 -0.0369  11.00000  0.05    0.27
Q14   1   0.2583  0.7960  0.4010  11.00000  0.05    0.27
Q15   1   0.1933  0.4959  0.1621  11.00000  0.05    0.26
Q16   1  -0.0569  0.7745  0.2297  11.00000  0.05    0.26
Q17   1   0.2261  0.6233  0.2758  11.00000  0.05    0.26
Q18   1   0.3119  0.9974  0.0833  11.00000  0.05    0.26
Q19   1  -0.0241  0.6188  0.1685  11.00000  0.05    0.26
Q20   1  -0.0542  0.6962  0.4398  11.00000  0.05    0.26
;
_shelx_res_checksum              35967
####################################################################### 
# 
# 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_151120a_0m
_database_code_depnum_ccdc_archive 'CCDC 1441551'
loop_
_audit_author_name
_audit_author_address
'Jifeng Chen'
;beijing institute of technology
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2019-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H6 F2 N4 O4'
_chemical_formula_weight         200.12

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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   6.042(5)
_cell_length_b                   9.000(8)
_cell_length_c                   13.277(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     721.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2007
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      28.14

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.944
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4448
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.069
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             889
_reflns_number_gt                794
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²+0.3541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         889
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.250000 0.750000 -0.01736(14) 0.0270(5) Uani 1 2 d S T P . .
C2 C 0.0708(2) 0.73664(15) 0.06332(9) 0.0205(3) Uani 1 1 d . . . . .
H2A H -0.036287 0.819913 0.063409 0.025 Uiso 1 1 calc R U . . .
H2B H -0.006470 0.639636 0.063409 0.025 Uiso 1 1 calc R U . . .
F1 F 0.22905(15) 0.87013(16) -0.07844(7) 0.0543(4) Uani 1 1 d . . . . .
N1 N 0.250000 0.750000 0.14330(11) 0.0180(3) Uani 1 2 d S T P . .
H1A H 0.263674 0.667331 0.182269 0.022 Uiso 0.5 1 calc R U P . .
H1B H 0.236327 0.832668 0.182270 0.022 Uiso 0.5 1 calc R U P . .
N2 N 0.21050(16) 0.12451(11) 0.18996(8) 0.0162(3) Uani 1 1 d . . . . .
N3 N 0.250000 0.250000 0.24667(11) 0.0200(4) Uani 1 2 d S T P . .
O1 O 0.27294(16) 0.10608(11) 0.10268(6) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.11822(16) 0.02377(10) 0.23978(7) 0.0235(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0161(8) 0.0510(13) 0.0137(8) 0.000 0.000 0.0002(8)
C2 0.0158(6) 0.0298(7) 0.0159(6) 0.0017(5) 0.0008(4) 0.0016(5)
F1 0.0248(5) 0.1041(10) 0.0341(5) 0.0416(6) -0.0021(4) -0.0034(5)
N1 0.0227(8) 0.0178(7) 0.0136(7) 0.000 0.000 0.0006(5)
N2 0.0138(5) 0.0170(5) 0.0177(5) 0.0007(4) -0.0004(4) 0.0015(4)
N3 0.0278(8) 0.0167(7) 0.0153(7) 0.000 0.000 -0.0006(6)
O1 0.0251(5) 0.0237(5) 0.0172(5) -0.0037(3) 0.0039(3) 0.0014(4)
O2 0.0253(5) 0.0192(5) 0.0259(5) 0.0038(4) 0.0050(4) -0.0032(4)

_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 F1 1.3575(17) 2_565 ?
C1 F1 1.3575(17) . ?
C1 C2 1.5277(19) 2_565 ?
C1 C2 1.5277(19) . ?
C2 N1 1.5213(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N2 O1 1.2299(16) . ?
N2 O2 1.2531(15) . ?
N2 N3 1.3781(15) . ?

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
F1 C1 F1 106.63(18) 2_565 . ?
F1 C1 C2 114.55(8) 2_565 2_565 ?
F1 C1 C2 114.98(8) . 2_565 ?
F1 C1 C2 114.98(8) 2_565 . ?
F1 C1 C2 114.55(7) . . ?
C2 C1 C2 90.97(15) 2_565 . ?
N1 C2 C1 88.78(11) . . ?
N1 C2 H2A 113.9 . . ?
C1 C2 H2A 113.9 . . ?
N1 C2 H2B 113.9 . . ?
C1 C2 H2B 113.9 . . ?
H2A C2 H2B 111.1 . . ?
C2 N1 C2 91.46(13) . 2_565 ?
C2 N1 H1A 113.4 . . ?
C2 N1 H1A 113.4 2_565 . ?
C2 N1 H1B 113.4 . . ?
C2 N1 H1B 113.4 2_565 . ?
H1A N1 H1B 110.7 . . ?
O1 N2 O2 122.42(11) . . ?
O1 N2 N3 124.90(11) . . ?
O2 N2 N3 112.44(11) . . ?
N2 N3 N2 113.78(15) 2 . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.065

_shelx_res_file                  
;

TITL 151120a_0m in Pccn
    151120a_0m.res
    created by SHELXL-2018/3 at 17:31:11 on 15-Aug-2019
CELL 0.71073   6.04150   9.00000  13.27690  90.0000  90.0000  90.0000
ZERR    4.00   0.00500   0.00760   0.01070   0.0000   0.0000   0.0000
LATT 1
SYMM 0.5-X, 0.5-Y, Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, -Y, 0.5-Z
SFAC C  H  N  O  F
UNIT 12  24  16  16  8
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 5
ACTA
BOND $H
FMAP 2
PLAN 5
SIZE 0.40 0.36 0.30
TEMP -173.000
WGHT    0.031800    0.354100
EXTI    0.038290
FVAR       0.22258
MOLE 2
C1    1    0.250000    0.750000   -0.017356    10.50000    0.01615    0.05098 =
         0.01372    0.00000    0.00000    0.00019
C2    1    0.070786    0.736643    0.063318    11.00000    0.01579    0.02983 =
         0.01586    0.00173    0.00077    0.00165
AFIX  23
H2A   2   -0.036287    0.819913    0.063409    11.00000   -1.20000
H2B   2   -0.006470    0.639636    0.063409    11.00000   -1.20000
AFIX   0
F1    5    0.229052    0.870134   -0.078441    11.00000    0.02478    0.10412 =
         0.03413    0.04163   -0.00213   -0.00344
N1    3    0.250000    0.750000    0.143299    10.50000    0.02269    0.01776 =
         0.01355    0.00000    0.00000    0.00058
AFIX  23
H1A   2    0.263674    0.667331    0.182269    10.50000   -1.20000
H1B   2    0.236327    0.832668    0.182270    10.50000   -1.20000
AFIX   0
MOLE 1
N2    3    0.210501    0.124511    0.189963    11.00000    0.01384    0.01698 =
         0.01775    0.00071   -0.00035    0.00152
N3    3    0.250000    0.250000    0.246666    10.50000    0.02785    0.01669 =
         0.01532    0.00000    0.00000   -0.00063
O1    4    0.272945    0.106076    0.102680    11.00000    0.02515    0.02374 =
         0.01725   -0.00368    0.00387    0.00136
O2    4    0.118223    0.023774    0.239776    11.00000    0.02525    0.01921 =
         0.02593    0.00377    0.00501   -0.00318
HKLF 4




REM  151120a_0m in Pccn
REM wR2 = 0.094813, GooF = S = 1.06069, Restrained GooF = 1.06069 for all data
REM R1 = 0.036052 for 794 Fo > 4sig(Fo) and 0.040561 for all 889 data
REM 62 parameters refined using 0 restraints

END

WGHT      0.0301      0.3927

REM Highest difference peak  0.349,  deepest hole -0.318,  1-sigma level  0.065
Q1    1   0.1533  0.7439  0.0154  11.00000  0.05    0.35
Q2    1   0.2474  0.8994 -0.0642  11.00000  0.05    0.26
Q3    1   0.1556  0.7423  0.1058  11.00000  0.05    0.24
Q4    1   0.2197  0.8236 -0.1166  11.00000  0.05    0.19
Q5    1   0.2337  0.0263  0.0802  11.00000  0.05    0.19
;
_shelx_res_checksum              13094
