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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2205686'
loop_
_audit_author_name
_audit_author_address
'Fan-zhi Bu '
;Ocean University of China
China
;
_audit_update_record             
;
2022-09-07 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 F N3 O5'
_chemical_formula_weight         283.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4921(2)
_cell_length_b                   6.37760(10)
_cell_length_c                   12.2609(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.057(2)
_cell_angle_gamma                90
_cell_volume                     562.99(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10117
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      27.54

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.255
_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      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Brooker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3529
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.751
_diffrn_reflns_theta_max         71.897
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_point_group_measured_fraction_full 0.898
_reflns_number_total             1917
_reflns_number_gt                1906
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_max     0.748
_reflns_Friedel_fraction_full    0.775

_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0361P)²+0.0871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1917
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0622
_refine_ls_wR_factor_gt          0.0621
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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 0.27950(15) -0.22535(18) 0.56331(8) 0.0171(3) Uani 1 1 d . . . . .
O1 O 0.32979(16) 0.0573(2) 0.98107(10) 0.0129(3) Uani 1 1 d . . . . .
N1 N 0.2228(2) 0.0987(2) 0.78918(12) 0.0106(3) Uani 1 1 d . . . . .
H3 H 0.167331 0.216303 0.798570 0.013 Uiso 1 1 calc R U . . .
N2 N 0.3979(2) -0.1925(3) 0.86624(12) 0.0115(3) Uani 1 1 d . . . . .
H2 H 0.460202 -0.265833 0.925329 0.014 Uiso 1 1 calc R U . . .
N3 N 0.1212(2) 0.1514(3) 0.59502(12) 0.0124(3) Uani 1 1 d . . . . .
H4 H 0.070314 0.270753 0.606519 0.015 Uiso 1 1 calc R U . . .
H5 H 0.112911 0.109594 0.525394 0.015 Uiso 1 1 calc R U . . .
C1 C 0.3179(2) -0.0096(3) 0.88514(14) 0.0103(4) Uani 1 1 d . . . . .
C2 C 0.3866(2) -0.2682(3) 0.76036(14) 0.0117(4) Uani 1 1 d . . . . .
H1 H 0.443661 -0.397740 0.751486 0.014 Uiso 1 1 calc R U . . .
C3 C 0.2947(2) -0.1583(3) 0.66935(14) 0.0119(4) Uani 1 1 d . . . . .
C4 C 0.2089(2) 0.0363(3) 0.68127(14) 0.0104(3) Uani 1 1 d . . . . .
O2 O -0.04326(17) -0.0487(2) 0.18232(10) 0.0125(3) Uani 1 1 d . . . . .
O3 O 0.05220(18) 0.0102(2) 0.36799(10) 0.0143(3) Uani 1 1 d . . . . .
O4 O 0.23358(17) 0.5796(2) 0.01901(10) 0.0142(3) Uani 1 1 d . . . . .
H9 H 0.160584 0.513236 -0.034149 0.021 Uiso 1 1 calc R U . . .
O5 O 0.37391(17) 0.8251(2) 0.19389(10) 0.0140(3) Uani 1 1 d . . . . .
H8 H 0.341003 0.853080 0.124230 0.021 Uiso 1 1 calc R U . . .
C5 C 0.0438(2) 0.0601(3) 0.26750(14) 0.0106(4) Uani 1 1 d . . . . .
C6 C 0.1366(2) 0.2593(3) 0.24748(14) 0.0113(4) Uani 1 1 d . . . . .
C7 C 0.1357(2) 0.3202(3) 0.13734(14) 0.0106(3) Uani 1 1 d . . . . .
H10 H 0.079807 0.232419 0.074596 0.013 Uiso 1 1 calc R U . . .
C8 C 0.2164(2) 0.5083(3) 0.12009(13) 0.0112(4) Uani 1 1 d . . . . .
C9 C 0.2964(2) 0.6401(3) 0.21219(14) 0.0115(4) Uani 1 1 d . . . . .
C10 C 0.3012(2) 0.5792(3) 0.32172(14) 0.0131(4) Uani 1 1 d . . . . .
H7 H 0.357835 0.666799 0.384390 0.016 Uiso 1 1 calc R U . . .
C11 C 0.2226(2) 0.3893(3) 0.33892(15) 0.0127(4) Uani 1 1 d . . . . .
H6 H 0.227166 0.346920 0.413921 0.015 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.3432(19) . ?
O1 C1 1.231(2) . ?
N1 C4 1.358(2) . ?
N1 C1 1.380(2) . ?
N1 H3 0.8800 . ?
N2 C1 1.360(3) . ?
N2 C2 1.366(2) . ?
N2 H2 0.8800 . ?
N3 C4 1.306(2) . ?
N3 H4 0.8800 . ?
N3 H5 0.8800 . ?
C2 C3 1.336(3) . ?
C2 H1 0.9500 . ?
C3 C4 1.424(3) . ?
O2 C5 1.273(2) . ?
O3 C5 1.257(2) . ?
O4 C8 1.359(2) . ?
O4 H9 0.8400 . ?
O5 C9 1.361(2) . ?
O5 H8 0.8400 . ?
C5 C6 1.501(3) . ?
C6 C11 1.400(3) . ?
C6 C7 1.403(2) . ?
C7 C8 1.385(3) . ?
C7 H10 0.9500 . ?
C8 C9 1.403(2) . ?
C9 C10 1.389(2) . ?
C10 C11 1.388(3) . ?
C10 H7 0.9500 . ?
C11 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 124.47(16) . . ?
C4 N1 H3 117.8 . . ?
C1 N1 H3 117.8 . . ?
C1 N2 C2 123.42(15) . . ?
C1 N2 H2 118.3 . . ?
C2 N2 H2 118.3 . . ?
C4 N3 H4 120.0 . . ?
C4 N3 H5 120.0 . . ?
H4 N3 H5 120.0 . . ?
O1 C1 N2 122.74(15) . . ?
O1 C1 N1 121.68(17) . . ?
N2 C1 N1 115.58(15) . . ?
C3 C2 N2 119.37(17) . . ?
C3 C2 H1 120.3 . . ?
N2 C2 H1 120.3 . . ?
C2 C3 F1 121.83(17) . . ?
C2 C3 C4 120.97(16) . . ?
F1 C3 C4 117.20(15) . . ?
N3 C4 N1 120.65(18) . . ?
N3 C4 C3 123.19(15) . . ?
N1 C4 C3 116.16(16) . . ?
C8 O4 H9 109.5 . . ?
C9 O5 H8 109.5 . . ?
O3 C5 O2 122.78(16) . . ?
O3 C5 C6 118.35(15) . . ?
O2 C5 C6 118.85(14) . . ?
C11 C6 C7 119.04(16) . . ?
C11 C6 C5 120.12(15) . . ?
C7 C6 C5 120.83(15) . . ?
C8 C7 C6 120.02(15) . . ?
C8 C7 H10 120.0 . . ?
C6 C7 H10 120.0 . . ?
O4 C8 C7 125.75(15) . . ?
O4 C8 C9 113.98(16) . . ?
C7 C8 C9 120.23(15) . . ?
O5 C9 C10 120.27(16) . . ?
O5 C9 C8 119.59(15) . . ?
C10 C9 C8 120.12(17) . . ?
C11 C10 C9 119.50(17) . . ?
C11 C10 H7 120.2 . . ?
C9 C10 H7 120.2 . . ?
C10 C11 C6 121.04(16) . . ?
C10 C11 H6 119.5 . . ?
C6 C11 H6 119.5 . . ?

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
C2 N2 C1 O1 -179.70(15) . . . . ?
C2 N2 C1 N1 -0.2(2) . . . . ?
C4 N1 C1 O1 178.14(16) . . . . ?
C4 N1 C1 N2 -1.3(2) . . . . ?
C1 N2 C2 C3 0.8(3) . . . . ?
N2 C2 C3 F1 179.91(15) . . . . ?
N2 C2 C3 C4 0.2(3) . . . . ?
C1 N1 C4 N3 -177.78(15) . . . . ?
C1 N1 C4 C3 2.2(2) . . . . ?
C2 C3 C4 N3 178.42(17) . . . . ?
F1 C3 C4 N3 -1.3(2) . . . . ?
C2 C3 C4 N1 -1.5(2) . . . . ?
F1 C3 C4 N1 178.69(14) . . . . ?
O3 C5 C6 C11 -2.9(2) . . . . ?
O2 C5 C6 C11 175.69(16) . . . . ?
O3 C5 C6 C7 178.38(15) . . . . ?
O2 C5 C6 C7 -3.1(2) . . . . ?
C11 C6 C7 C8 -1.1(2) . . . . ?
C5 C6 C7 C8 177.69(16) . . . . ?
C6 C7 C8 O4 176.22(15) . . . . ?
C6 C7 C8 C9 -1.1(2) . . . . ?
O4 C8 C9 O5 2.9(2) . . . . ?
C7 C8 C9 O5 -179.53(15) . . . . ?
O4 C8 C9 C10 -175.24(15) . . . . ?
C7 C8 C9 C10 2.4(2) . . . . ?
O5 C9 C10 C11 -179.54(14) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C9 C10 C11 C6 -0.7(3) . . . . ?
C7 C6 C11 C10 2.0(2) . . . . ?
C5 C6 C11 C10 -176.78(15) . . . . ?

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042



