# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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 2122797'
loop_
_audit_author_name
_audit_author_address
'Fan-Zhi Bu'
;Ocean University of China
China
;
_audit_update_record             
;
2021-11-18 deposited with the CCDC.	2022-03-01 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            'C12 H14 F N3 O6'
_chemical_formula_weight         315.26

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.6344(3)
_cell_length_b                   6.3521(3)
_cell_length_c                   28.5161(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.7030(10)
_cell_angle_gamma                90
_cell_volume                     1382.77(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    10208
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      27.54

_exptl_crystal_description       rod
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.978
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20898
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.286
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3171
_reflns_number_gt                2358
_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-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)+(0.0521P)²+0.2145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3171
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0944
_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 0.50121(14) 0.03824(15) 0.21915(3) 0.0555(3) Uani 1 1 d . . . . .
O14 O 0.34741(14) 0.36029(16) 0.05160(3) 0.0416(3) Uani 1 1 d . . . . .
N3 N 0.34019(14) 0.39333(17) 0.13078(4) 0.0291(3) Uani 1 1 d . . . . .
N4 N 0.45739(16) 0.09316(19) 0.09533(4) 0.0342(3) Uani 1 1 d . . . . .
N5 N 0.34147(19) 0.4212(2) 0.21099(4) 0.0419(3) Uani 1 1 d . . . . .
C6 C 0.37938(17) 0.2863(2) 0.09105(4) 0.0295(3) Uani 1 1 d . . . . .
C7 C 0.49918(19) 0.0071(2) 0.13757(5) 0.0356(3) Uani 1 1 d . . . . .
C8 C 0.46329(18) 0.1145(2) 0.17610(5) 0.0337(3) Uani 1 1 d . . . . .
C9 C 0.38010(17) 0.3138(2) 0.17287(4) 0.0289(3) Uani 1 1 d . . . . .
O17 O 0.35649(13) 0.24091(16) 0.38511(3) 0.0358(3) Uani 1 1 d . . . . .
O18 O 0.37525(14) 0.28062(16) 0.30787(3) 0.0407(3) Uani 1 1 d . . . . .
O19 O 0.66959(15) 0.86908(17) 0.45474(3) 0.0474(3) Uani 1 1 d . . . . .
O20 O 0.76099(14) 1.10069(16) 0.38214(4) 0.0424(3) Uani 1 1 d . . . . .
C21 C 0.40791(17) 0.3424(2) 0.34757(4) 0.0285(3) Uani 1 1 d . . . . .
C22 C 0.50568(17) 0.5388(2) 0.35732(4) 0.0291(3) Uani 1 1 d . . . . .
C23 C 0.54128(18) 0.6013(2) 0.40335(5) 0.0314(3) Uani 1 1 d . . . . .
C24 C 0.62636(18) 0.7890(2) 0.41182(5) 0.0318(3) Uani 1 1 d . . . . .
C25 C 0.67708(17) 0.9158(2) 0.37427(5) 0.0320(3) Uani 1 1 d . . . . .
C26 C 0.64146(19) 0.8543(2) 0.32896(5) 0.0360(3) Uani 1 1 d . . . . .
C27 C 0.55619(19) 0.6655(2) 0.32033(5) 0.0344(3) Uani 1 1 d . . . . .
C28 C 0.6102(3) 0.7580(3) 0.49487(5) 0.0509(5) Uani 1 1 d . . . . .
O2 O 0.54733(18) 0.74446(19) 0.03780(4) 0.0463(3) Uani 1 1 d . . . . .
H10 H 0.555(2) -0.123(3) 0.1383(6) 0.055(5) Uiso 1 1 d . . . . .
H11 H 0.477(2) 0.021(3) 0.0700(6) 0.049(5) Uiso 1 1 d . . . . .
H12 H 0.280(2) 0.542(3) 0.2082(6) 0.056(5) Uiso 1 1 d . . . . .
H13 H 0.367(2) 0.375(3) 0.2390(6) 0.047(5) Uiso 1 1 d . . . . .
H29 H 0.298(3) 0.127(3) 0.3768(7) 0.064(6) Uiso 1 1 d . . . . .
H30 H 0.780(2) 1.117(3) 0.4115(7) 0.052(5) Uiso 1 1 d . . . . .
H31 H 0.5044(18) 0.512(2) 0.4296(5) 0.035(4) Uiso 1 1 d . . . . .
H32 H 0.681(2) 0.945(3) 0.3047(6) 0.045(4) Uiso 1 1 d . . . . .
H33 H 0.5319(19) 0.624(2) 0.2888(6) 0.038(4) Uiso 1 1 d . . . . .
H34 H 0.482(3) 0.738(3) 0.4933(6) 0.056(5) Uiso 1 1 d . . . . .
H35 H 0.667(2) 0.615(3) 0.4954(7) 0.065(6) Uiso 1 1 d . . . . .
H36 H 0.645(2) 0.837(3) 0.5219(7) 0.062(5) Uiso 1 1 d . . . . .
H15 H 0.469(3) 0.640(4) 0.0405(8) 0.099(9) Uiso 1 1 d . . . . .
H16 H 0.579(3) 0.727(3) 0.0099(8) 0.067(6) 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
F1 C8 1.3478(15) . ?
O14 C6 1.2405(16) . ?
N3 C9 1.3344(16) . ?
N3 C6 1.3578(17) . ?
N4 C7 1.3573(18) . ?
N4 C6 1.3685(17) . ?
N4 H11 0.870(19) . ?
N5 C9 1.3200(18) . ?
N5 H12 0.90(2) . ?
N5 H13 0.873(18) . ?
C7 C8 1.325(2) . ?
C7 H10 0.930(19) . ?
C8 C9 1.4186(19) . ?
O17 C21 1.3138(16) . ?
O17 H29 0.88(2) . ?
O18 C21 1.2208(16) . ?
O19 C24 1.3623(16) . ?
O19 C28 1.4230(19) . ?
O20 C25 1.3550(16) . ?
O20 H30 0.855(19) . ?
C21 C22 1.4786(18) . ?
C22 C27 1.3854(19) . ?
C22 C23 1.3947(18) . ?
C23 C24 1.3779(19) . ?
C23 H31 0.982(16) . ?
C24 C25 1.3986(19) . ?
C25 C26 1.374(2) . ?
C26 C27 1.385(2) . ?
C26 H32 0.954(17) . ?
C27 H33 0.955(16) . ?
C28 H34 0.990(19) . ?
C28 H35 1.00(2) . ?
C28 H36 0.95(2) . ?
O2 H15 0.89(3) . ?
O2 H16 0.84(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
C9 N3 C6 120.72(11) . . ?
C7 N4 C6 122.51(12) . . ?
C7 N4 H11 119.0(11) . . ?
C6 N4 H11 118.4(11) . . ?
C9 N5 H12 119.3(11) . . ?
C9 N5 H13 121.9(11) . . ?
H12 N5 H13 118.7(16) . . ?
O14 C6 N3 121.60(12) . . ?
O14 C6 N4 120.07(12) . . ?
N3 C6 N4 118.33(11) . . ?
C8 C7 N4 118.68(13) . . ?
C8 C7 H10 122.6(11) . . ?
N4 C7 H10 118.7(11) . . ?
C7 C8 F1 121.73(12) . . ?
C7 C8 C9 120.18(13) . . ?
F1 C8 C9 118.08(12) . . ?
N5 C9 N3 119.62(13) . . ?
N5 C9 C8 120.82(12) . . ?
N3 C9 C8 119.56(12) . . ?
C21 O17 H29 109.8(13) . . ?
C24 O19 C28 117.47(11) . . ?
C25 O20 H30 110.2(13) . . ?
O18 C21 O17 122.58(12) . . ?
O18 C21 C22 122.85(12) . . ?
O17 C21 C22 114.57(11) . . ?
C27 C22 C23 119.90(13) . . ?
C27 C22 C21 119.44(12) . . ?
C23 C22 C21 120.61(12) . . ?
C24 C23 C22 119.82(12) . . ?
C24 C23 H31 120.2(9) . . ?
C22 C23 H31 120.0(9) . . ?
O19 C24 C23 126.11(12) . . ?
O19 C24 C25 113.99(12) . . ?
C23 C24 C25 119.91(12) . . ?
O20 C25 C26 119.35(12) . . ?
O20 C25 C24 120.47(13) . . ?
C26 C25 C24 120.18(13) . . ?
C25 C26 C27 120.05(13) . . ?
C25 C26 H32 116.6(10) . . ?
C27 C26 H32 123.3(10) . . ?
C26 C27 C22 120.14(13) . . ?
C26 C27 H33 119.6(9) . . ?
C22 C27 H33 120.2(9) . . ?
O19 C28 H34 110.7(11) . . ?
O19 C28 H35 108.7(11) . . ?
H34 C28 H35 108.1(15) . . ?
O19 C28 H36 107.6(12) . . ?
H34 C28 H36 111.4(16) . . ?
H35 C28 H36 110.3(16) . . ?
H15 O2 H16 100(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
C9 N3 C6 O14 -178.09(12) . . . . ?
C9 N3 C6 N4 1.34(19) . . . . ?
C7 N4 C6 O14 178.35(13) . . . . ?
C7 N4 C6 N3 -1.1(2) . . . . ?
C6 N4 C7 C8 -0.1(2) . . . . ?
N4 C7 C8 F1 179.96(12) . . . . ?
N4 C7 C8 C9 1.1(2) . . . . ?
C6 N3 C9 N5 179.66(13) . . . . ?
C6 N3 C9 C8 -0.4(2) . . . . ?
C7 C8 C9 N5 179.10(14) . . . . ?
F1 C8 C9 N5 0.2(2) . . . . ?
C7 C8 C9 N3 -0.8(2) . . . . ?
F1 C8 C9 N3 -179.75(12) . . . . ?
O18 C21 C22 C27 3.2(2) . . . . ?
O17 C21 C22 C27 -175.80(12) . . . . ?
O18 C21 C22 C23 -179.30(13) . . . . ?
O17 C21 C22 C23 1.70(18) . . . . ?
C27 C22 C23 C24 0.1(2) . . . . ?
C21 C22 C23 C24 -177.39(12) . . . . ?
C28 O19 C24 C23 -5.2(2) . . . . ?
C28 O19 C24 C25 175.07(15) . . . . ?
C22 C23 C24 O19 -179.89(13) . . . . ?
C22 C23 C24 C25 -0.2(2) . . . . ?
O19 C24 C25 O20 -0.2(2) . . . . ?
C23 C24 C25 O20 -179.93(12) . . . . ?
O19 C24 C25 C26 -179.90(12) . . . . ?
C23 C24 C25 C26 0.4(2) . . . . ?
O20 C25 C26 C27 179.82(13) . . . . ?
C24 C25 C26 C27 -0.5(2) . . . . ?
C25 C26 C27 C22 0.4(2) . . . . ?
C23 C22 C27 C26 -0.2(2) . . . . ?
C21 C22 C27 C26 177.32(13) . . . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.051



